data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Ayesha Jacobs' _publ_contact_author_address ; Interdisciplinary Maths and Science Studies Cape Technikon PO Box 652 Cape Town 8000 Cape Town SOUTH AFRICA ; _publ_contact_author_email JACOBSA@CTECH.AC.ZA _publ_section_title ; Xanthenol Clathrates: structure, thermal stability, guest exchange and kinetics of desolvation. ; loop_ _publ_author_name 'Ayesha Jacobs' 'Luigi R. Nassimbeni' 'Hong Su.' 'Benjamin Taljaard' data_1a _database_code_depnum_ccdc_archive 'CCDC 239532' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol p-xylene clathrate ; _chemical_formula_moiety 'C20 H16 O3.C4 H5' _chemical_formula_sum 'C24 H21 O3' _chemical_formula_weight 357.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3773(2) _cell_length_b 9.1657(3) _cell_length_c 12.7261(4) _cell_angle_alpha 94.8100(10) _cell_angle_beta 96.3740(10) _cell_angle_gamma 108.9480(10) _cell_volume 910.99(5) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description rectangle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9816 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1.0\%, 60s per \%, 2 iterations. ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 3932 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.16 _reflns_number_total 3932 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai & Pritzkow, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1429P)^2^+0.0253P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef N/A _refine_ls_number_reflns 3932 _refine_ls_number_parameters 250 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.2074 _refine_ls_wR_factor_gt 0.1596 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.28014(14) 0.21733(13) 0.47030(8) 0.0177(3) Uani 1 1 d D . . H1 H -0.213(3) 0.3092(17) 0.5168(15) 0.050(7) Uiso 1 1 d D . . O2 O 0.07446(14) 0.51309(13) 0.38629(10) 0.0207(3) Uani 1 1 d . . . O3 O -0.65430(17) -0.30850(14) 0.09196(10) 0.0282(3) Uani 1 1 d . . . C1 C -0.03428(19) 0.23238(19) 0.38368(12) 0.0160(4) Uani 1 1 d . . . C2 C 0.0074(2) 0.0980(2) 0.39341(13) 0.0196(4) Uani 1 1 d . . . H2 H -0.0809 -0.0003 0.3816 0.024 Uiso 1 1 calc R . . C3 C 0.1750(2) 0.1052(2) 0.41997(14) 0.0221(4) Uani 1 1 d . . . H3 H 0.2006 0.0123 0.4261 0.026 Uiso 1 1 calc R . . C4 C 0.3055(2) 0.2484(2) 0.43759(13) 0.0219(4) Uani 1 1 d . . . H4 H 0.4200 0.2539 0.4581 0.026 Uiso 1 1 calc R . . C5 C 0.2683(2) 0.3824(2) 0.42529(14) 0.0212(4) Uani 1 1 d . . . H5 H 0.3573 0.4803 0.4352 0.025 Uiso 1 1 calc R . . C6 C 0.0994(2) 0.37297(19) 0.39814(13) 0.0171(4) Uani 1 1 d . . . C7 C -0.22810(19) 0.37609(18) 0.32715(12) 0.0156(4) Uani 1 1 d . . . C8 C -0.3823(2) 0.3884(2) 0.28178(13) 0.0199(4) Uani 1 1 d . . . H8 H -0.4821 0.2988 0.2699 0.024 Uiso 1 1 calc R . . C9 C -0.3929(2) 0.5278(2) 0.25379(14) 0.0227(4) Uani 1 1 d . . . H9 H -0.4997 0.5338 0.2246 0.027 Uiso 1 1 calc R . . C10 C -0.2468(2) 0.6595(2) 0.26849(14) 0.0236(4) Uani 1 1 d . . . H10 H -0.2534 0.7554 0.2490 0.028 Uiso 1 1 calc R . . C11 C -0.0930(2) 0.6497(2) 0.31145(14) 0.0216(4) Uani 1 1 d . . . H11 H 0.0076 0.7386 0.3208 0.026 Uiso 1 1 calc R . . C12 C -0.0854(2) 0.50957(19) 0.34108(13) 0.0176(4) Uani 1 1 d . . . C13 C -0.21902(19) 0.22715(18) 0.36839(12) 0.0158(4) Uani 1 1 d . . . C14 C -0.3356(2) 0.08271(18) 0.29473(13) 0.0164(4) Uani 1 1 d . . . C15 C -0.3031(2) 0.05736(19) 0.19109(13) 0.0200(4) Uani 1 1 d . . . H15 H -0.2076 0.1296 0.1683 0.024 Uiso 1 1 calc R . . C16 C -0.4062(2) -0.0705(2) 0.12010(13) 0.0212(4) Uani 1 1 d . . . H16 H -0.3824 -0.0852 0.0495 0.025 Uiso 1 1 calc R . . C17 C -0.5447(2) -0.17617(19) 0.15406(14) 0.0208(4) Uani 1 1 d . . . C18 C -0.5780(2) -0.1538(2) 0.25742(14) 0.0218(4) Uani 1 1 d . . . H18 H -0.6728 -0.2268 0.2803 0.026 Uiso 1 1 calc R . . C19 C -0.4738(2) -0.02530(19) 0.32775(13) 0.0192(4) Uani 1 1 d . . . H19 H -0.4972 -0.0113 0.3985 0.023 Uiso 1 1 calc R . . C20 C -0.6195(3) -0.3388(2) -0.01277(15) 0.0355(5) Uani 1 1 d . . . H20A H -0.6181 -0.2509 -0.0519 0.053 Uiso 1 1 calc R . . H20B H -0.7082 -0.4334 -0.0497 0.053 Uiso 1 1 calc R . . H20C H -0.5082 -0.3532 -0.0090 0.053 Uiso 1 1 calc R . . C1G C 0.0620(3) 0.1532(3) 0.05281(17) 0.0382(5) Uani 1 1 d . . . C2G C 0.1032(3) 0.0346(3) 0.09674(16) 0.0408(6) Uani 1 1 d . . . H2G H 0.1745 0.0570 0.1637 0.049 Uiso 1 1 calc R . . C3G C 0.0426(3) -0.1156(3) 0.04517(18) 0.0402(6) Uani 1 1 d . . . H3G H 0.0729 -0.1947 0.0772 0.048 Uiso 1 1 calc R . . C4G C 0.1273(4) 0.3170(3) 0.1095(2) 0.0696(9) Uani 1 1 d . . . H4G1 H 0.2333 0.3758 0.0844 0.104 Uiso 1 1 calc R . . H4G2 H 0.1495 0.3147 0.1864 0.104 Uiso 1 1 calc R . . H4G3 H 0.0417 0.3671 0.0944 0.104 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0165(6) 0.0189(6) 0.0170(6) 0.0016(5) 0.0032(5) 0.0048(5) O2 0.0147(6) 0.0148(6) 0.0315(7) 0.0020(5) -0.0019(5) 0.0057(5) O3 0.0316(7) 0.0197(7) 0.0269(7) -0.0057(5) -0.0050(5) 0.0053(6) C1 0.0140(8) 0.0183(8) 0.0159(8) 0.0010(6) 0.0009(6) 0.0066(6) C2 0.0170(8) 0.0184(9) 0.0242(9) 0.0041(7) 0.0014(7) 0.0072(7) C3 0.0207(9) 0.0213(9) 0.0277(9) 0.0039(7) 0.0026(7) 0.0118(7) C4 0.0155(8) 0.0277(10) 0.0249(9) 0.0036(7) 0.0020(7) 0.0108(7) C5 0.0140(8) 0.0220(9) 0.0257(9) 0.0009(7) 0.0002(7) 0.0047(7) C6 0.0173(8) 0.0168(8) 0.0187(8) 0.0016(6) 0.0017(6) 0.0082(7) C7 0.0149(8) 0.0159(8) 0.0168(8) 0.0010(6) 0.0015(6) 0.0068(6) C8 0.0160(8) 0.0194(9) 0.0237(9) 0.0017(7) 0.0000(7) 0.0065(7) C9 0.0197(9) 0.0224(9) 0.0264(9) 0.0011(7) -0.0039(7) 0.0104(7) C10 0.0248(9) 0.0184(9) 0.0292(10) 0.0042(7) -0.0005(7) 0.0105(7) C11 0.0187(8) 0.0154(8) 0.0285(9) 0.0013(7) 0.0009(7) 0.0041(7) C12 0.0143(8) 0.0194(9) 0.0192(8) 0.0006(6) 0.0001(6) 0.0072(7) C13 0.0139(8) 0.0170(8) 0.0174(8) 0.0029(6) 0.0017(6) 0.0064(6) C14 0.0142(8) 0.0165(8) 0.0205(8) 0.0030(6) 0.0000(6) 0.0084(7) C15 0.0207(8) 0.0174(9) 0.0228(9) 0.0051(6) 0.0035(7) 0.0072(7) C16 0.0274(9) 0.0198(9) 0.0182(8) 0.0023(6) 0.0005(7) 0.0114(7) C17 0.0208(9) 0.0156(8) 0.0252(9) -0.0013(7) -0.0049(7) 0.0085(7) C18 0.0162(8) 0.0187(9) 0.0282(10) 0.0016(7) 0.0016(7) 0.0036(7) C19 0.0165(8) 0.0190(9) 0.0226(8) 0.0010(7) 0.0027(6) 0.0074(7) C20 0.0514(13) 0.0252(10) 0.0238(10) -0.0027(8) -0.0050(9) 0.0095(9) C1G 0.0274(10) 0.0407(12) 0.0406(12) 0.0030(9) 0.0165(9) 0.0004(9) C2G 0.0245(10) 0.0632(16) 0.0280(11) 0.0058(10) 0.0009(8) 0.0065(10) C3G 0.0355(12) 0.0483(14) 0.0427(13) 0.0198(10) 0.0135(10) 0.0161(10) C4G 0.0634(18) 0.0485(16) 0.078(2) -0.0089(14) 0.0385(15) -0.0119(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4454(18) . ? O1 H1 0.954(7) . ? O2 C6 1.3839(19) . ? O2 C12 1.3866(19) . ? O3 C17 1.376(2) . ? O3 C20 1.420(2) . ? C1 C2 1.396(2) . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C3 1.391(2) . ? C4 H4 0.9500 . ? C5 C4 1.378(2) . ? C5 C6 1.392(2) . ? C5 H5 0.9500 . ? C6 C1 1.388(2) . ? C7 C12 1.387(2) . ? C7 C8 1.398(2) . ? C8 C9 1.382(2) . ? C8 H8 0.9500 . ? C9 C10 1.393(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C10 1.376(2) . ? C11 C12 1.388(2) . ? C11 H11 0.9500 . ? C13 C1 1.523(2) . ? C13 C7 1.524(2) . ? C14 C19 1.390(2) . ? C14 C15 1.392(2) . ? C14 C13 1.528(2) . ? C15 H15 0.9500 . ? C16 C17 1.386(2) . ? C16 C15 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.387(3) . ? C18 H18 0.9500 . ? C19 C18 1.390(2) . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C1G C3G 1.390(3) 2 ? C1G C4G 1.507(3) . ? C2G C3G 1.380(3) . ? C2G C1G 1.384(3) . ? C2G H2G 0.9500 . ? C3G C1G 1.390(3) 2 ? C3G H3G 0.9500 . ? C4G H4G1 0.9800 . ? C4G H4G2 0.9800 . ? C4G H4G3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C13 C1 108.73(12) . . ? O1 C13 C7 108.83(12) . . ? O1 C13 C14 106.34(12) . . ? O2 C6 C1 122.56(14) . . ? O2 C6 C5 115.38(14) . . ? O2 C12 C7 122.58(14) . . ? O2 C12 C11 115.21(14) . . ? O3 C17 C16 124.29(16) . . ? O3 C17 C18 115.57(15) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? C1 C6 C5 122.07(15) . . ? C1 C13 C7 109.31(13) . . ? C1 C13 C14 111.93(13) . . ? C1 C2 H2 119.3 . . ? C2 C1 C13 121.48(14) . . ? C2 C3 C4 119.88(16) . . ? C2 C3 H3 120.1 . . ? C3 C2 C1 121.39(16) . . ? C3 C2 H2 119.3 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.42(15) . . ? C4 C5 H5 120.3 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.88(15) . . ? C5 C4 H4 120.1 . . ? C6 O2 C12 118.20(12) . . ? C6 C5 H5 120.3 . . ? C6 C1 C2 117.28(14) . . ? C6 C1 C13 120.99(14) . . ? C7 C13 C14 111.58(12) . . ? C7 C8 H8 119.2 . . ? C7 C12 C11 122.21(15) . . ? C8 C7 C13 121.76(14) . . ? C8 C9 C10 119.89(15) . . ? C8 C9 H9 120.1 . . ? C9 C8 C7 121.61(15) . . ? C9 C8 H8 119.2 . . ? C9 C10 H10 120.2 . . ? C10 C9 H9 120.1 . . ? C10 C11 C12 119.71(16) . . ? C10 C11 H11 120.1 . . ? C11 C10 C9 119.59(16) . . ? C11 C10 H10 120.2 . . ? C12 C7 C8 116.97(15) . . ? C12 C7 C13 121.06(14) . . ? C12 C11 H11 120.1 . . ? C13 O1 H1 108.0(15) . . ? C14 C19 C18 120.15(16) . . ? C14 C15 H15 119.1 . . ? C14 C19 H19 119.9 . . ? C15 C14 C13 119.35(14) . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 120.13(15) . . ? C16 C15 C14 121.88(15) . . ? C16 C15 H15 119.1 . . ? C17 O3 C20 117.12(15) . . ? C17 C16 C15 118.83(16) . . ? C17 C16 H16 120.6 . . ? C17 C18 C19 120.51(16) . . ? C17 C18 H18 119.7 . . ? C18 C19 H19 119.9 . . ? C19 C14 C15 118.50(15) . . ? C19 C14 C13 122.14(15) . . ? C19 C18 H18 119.7 . . ? C1G C2G H2G 119.4 . . ? C1G C3G H3G 119.4 2 . ? C1G C4G H4G1 109.5 . . ? C1G C4G H4G2 109.5 . . ? C1G C4G H4G3 109.5 . . ? C2G C1G C3G 117.6(2) . 2 ? C2G C1G C4G 121.2(2) . . ? C2G C3G C1G 121.1(2) . 2 ? C2G C3G H3G 119.4 . . ? C3G C1G C4G 121.1(2) 2 . ? C3G C2G C1G 121.3(2) . . ? C3G C2G H2G 119.4 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H4G1 C4G H4G2 109.5 . . ? H4G1 C4G H4G3 109.5 . . ? H4G2 C4G H4G3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C13 C1 C6 -95.69(17) . . . . ? O1 C13 C7 C8 -77.10(18) . . . . ? O1 C13 C1 C2 78.40(17) . . . . ? O1 C13 C7 C12 97.55(16) . . . . ? O2 C6 C1 C13 -8.3(2) . . . . ? O2 C6 C1 C2 177.35(14) . . . . ? O3 C17 C18 C19 178.96(14) . . . . ? C1 C13 C7 C8 164.29(14) . . . . ? C1 C13 C7 C12 -21.1(2) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C4 C5 C6 O2 -179.28(14) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C5 C6 C1 C13 171.91(15) . . . . ? C5 C6 C1 C2 -2.4(2) . . . . ? C5 C4 C3 C2 -2.0(3) . . . . ? C6 C1 C2 C3 2.1(2) . . . . ? C6 O2 C12 C7 13.2(2) . . . . ? C6 O2 C12 C11 -167.36(14) . . . . ? C6 C5 C4 C3 1.8(3) . . . . ? C7 C13 C1 C6 23.0(2) . . . . ? C7 C13 C1 C2 -162.92(14) . . . . ? C7 C8 C9 C10 1.4(3) . . . . ? C8 C7 C12 O2 179.23(14) . . . . ? C8 C7 C12 C11 -0.2(2) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C10 C11 C12 O2 -178.24(15) . . . . ? C10 C11 C12 C7 1.2(3) . . . . ? C12 C11 C10 C9 -0.9(3) . . . . ? C12 O2 C6 C1 -11.1(2) . . . . ? C12 O2 C6 C5 168.64(14) . . . . ? C12 C7 C8 C9 -1.1(2) . . . . ? C13 C7 C8 C9 173.72(15) . . . . ? C13 C14 C19 C18 178.98(14) . . . . ? C13 C7 C12 O2 4.3(2) . . . . ? C13 C14 C15 C16 -178.93(14) . . . . ? C13 C1 C2 C3 -172.17(15) . . . . ? C13 C7 C12 C11 -175.11(15) . . . . ? C14 C19 C18 C17 0.4(3) . . . . ? C14 C13 C1 C6 147.13(15) . . . . ? C14 C13 C1 C2 -38.8(2) . . . . ? C14 C13 C7 C12 -145.41(15) . . . . ? C14 C13 C7 C8 39.9(2) . . . . ? C15 C14 C13 C7 63.91(19) . . . . ? C15 C14 C13 C1 -58.95(19) . . . . ? C15 C14 C13 O1 -177.55(13) . . . . ? C15 C16 C17 O3 -178.81(15) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C15 C14 C19 C18 -1.1(2) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C16 C15 C14 -0.5(3) . . . . ? C19 C14 C15 C16 1.2(2) . . . . ? C19 C14 C13 O1 2.3(2) . . . . ? C19 C14 C13 C1 120.95(16) . . . . ? C19 C14 C13 C7 -116.19(16) . . . . ? C20 O3 C17 C16 1.4(3) . . . . ? C20 O3 C17 C18 -177.24(15) . . . . ? C20 O3 C17 C16 1.4(3) . . . . ? C20 O3 C17 C18 -177.24(15) . . . . ? C1G C2G C3G C1G 0.0(3) . . . 2 ? C3G C2G C1G C3G 0.0(3) . . . 2 ? C3G C2G C1G C4G 179.63(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.954(7) 1.908(7) 2.8610(15) 177(2) 2_566 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.16 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.870 _refine_diff_density_min -1.037 _refine_diff_density_rms 0.318 _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol p-xylene clathrate' data_1b _database_code_depnum_ccdc_archive 'CCDC 239533' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol p-xylene clathrate ; _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol p-xylene clathrate' _chemical_formula_moiety 'C20 H16 O3.C4 H5' _chemical_formula_sum 'C24 H21 O3' _chemical_formula_weight 357.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3762(2) _cell_length_b 9.1588(3) _cell_length_c 12.7193(4) _cell_angle_alpha 94.8930(10) _cell_angle_beta 96.4010(10) _cell_angle_gamma 108.8720(10) _cell_volume 909.89(5) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description Cuboid _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9815 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1.0\%, 55s per \%, 2 iterations. ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 3966 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.17 _reflns_number_total 3966 _reflns_number_gt 3297 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.63(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3966 _refine_ls_number_parameters 251 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1330 _refine_ls_R_factor_gt 0.1137 _refine_ls_wR_factor_ref 0.3761 _refine_ls_wR_factor_gt 0.3574 _refine_ls_goodness_of_fit_ref 1.711 _refine_ls_restrained_S_all 1.710 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2799(2) 0.2169(2) 0.47026(14) 0.0206(6) Uani 1 1 d D . . O2 O 0.0736(2) 0.5129(2) 0.38612(16) 0.0237(6) Uani 1 1 d . . . O3 O -0.6551(3) -0.3090(2) 0.09187(17) 0.0324(7) Uani 1 1 d . . . C14 C -0.3360(3) 0.0817(3) 0.2947(2) 0.0204(7) Uani 1 1 d . . . C7 C -0.0339(3) 0.2318(3) 0.3834(2) 0.0189(7) Uani 1 1 d . . . C13 C -0.2187(3) 0.2270(3) 0.3681(2) 0.0193(7) Uani 1 1 d . . . C11 C 0.2680(4) 0.3825(3) 0.4255(2) 0.0237(7) Uani 1 1 d . . . H11 H 0.3567 0.4806 0.4357 0.028 Uiso 1 1 calc R . . C1 C -0.2270(3) 0.3759(3) 0.3273(2) 0.0185(7) Uani 1 1 d . . . C18 C -0.4073(4) -0.0718(3) 0.1196(2) 0.0259(7) Uani 1 1 d . . . H18 H -0.3837 -0.0869 0.0490 0.031 Uiso 1 1 calc R . . C12 C 0.0991(4) 0.3727(3) 0.3980(2) 0.0213(7) Uani 1 1 d . . . C10 C 0.3051(4) 0.2483(4) 0.4377(2) 0.0256(7) Uani 1 1 d . . . H10 H 0.4196 0.2538 0.4585 0.031 Uiso 1 1 calc R . . C17 C -0.5454(4) -0.1766(3) 0.1537(2) 0.0247(7) Uani 1 1 d . . . C3 C -0.3935(4) 0.5267(3) 0.2543(2) 0.0261(7) Uani 1 1 d . . . H3 H -0.5006 0.5325 0.2256 0.031 Uiso 1 1 calc R . . C16 C -0.5783(4) -0.1544(3) 0.2573(2) 0.0248(7) Uani 1 1 d . . . H16 H -0.6730 -0.2273 0.2802 0.030 Uiso 1 1 calc R . . C6 C -0.0869(4) 0.5095(3) 0.3409(2) 0.0214(7) Uani 1 1 d . . . C2 C -0.3827(4) 0.3873(3) 0.2820(2) 0.0225(7) Uani 1 1 d . . . H2 H -0.4823 0.2975 0.2702 0.027 Uiso 1 1 calc R . . C15 C -0.4733(4) -0.0259(3) 0.3276(2) 0.0224(7) Uani 1 1 d . . . H15 H -0.4960 -0.0120 0.3986 0.027 Uiso 1 1 calc R . . C8 C 0.0090(4) 0.0978(3) 0.3933(2) 0.0227(7) Uani 1 1 d . . . H8 H -0.0788 -0.0008 0.3816 0.027 Uiso 1 1 calc R . . C9 C 0.1755(4) 0.1057(3) 0.4197(2) 0.0255(7) Uani 1 1 d . . . H9 H 0.2017 0.0129 0.4256 0.031 Uiso 1 1 calc R . . C19 C -0.3035(4) 0.0562(3) 0.1909(2) 0.0229(7) Uani 1 1 d . . . H19 H -0.2079 0.1283 0.1681 0.027 Uiso 1 1 calc R . . C5 C -0.0938(4) 0.6503(3) 0.3119(2) 0.0254(7) Uani 1 1 d . . . H5 H 0.0064 0.7395 0.3221 0.031 Uiso 1 1 calc R . . C4 C -0.2481(4) 0.6589(3) 0.2683(2) 0.0270(7) Uani 1 1 d . . . H4 H -0.2553 0.7542 0.2478 0.032 Uiso 1 1 calc R . . C20 C -0.6204(5) -0.3390(4) -0.0133(3) 0.0406(9) Uani 1 1 d . . . H20A H -0.6207 -0.2515 -0.0524 0.061 Uiso 1 1 calc R . . H20B H -0.7082 -0.4343 -0.0502 0.061 Uiso 1 1 calc R . . H20C H -0.5084 -0.3520 -0.0097 0.061 Uiso 1 1 calc R . . C2G C 0.1029(5) 0.0350(5) 0.0969(3) 0.0507(11) Uani 1 1 d . . . H2G H 0.1740 0.0582 0.1640 0.061 Uiso 1 1 calc R . . C1G C 0.0607(5) 0.1537(5) 0.0518(3) 0.0464(10) Uani 1 1 d . . . C3G C 0.0433(5) -0.1153(5) 0.0459(3) 0.0470(10) Uani 1 1 d . . . H3G H 0.0741 -0.1939 0.0783 0.056 Uiso 1 1 calc R . . C4G C 0.1255(7) 0.3168(6) 0.1078(4) 0.0746(16) Uani 1 1 d . . . H4G1 H 0.2332 0.3744 0.0843 0.112 Uiso 1 1 calc R . . H4G2 H 0.1443 0.3149 0.1850 0.112 Uiso 1 1 calc R . . H4G3 H 0.0413 0.3679 0.0906 0.112 Uiso 1 1 calc R . . H1 H -0.226(4) 0.313(2) 0.517(2) 0.038(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0211(11) 0.0221(11) 0.0205(11) 0.0027(8) 0.0048(8) 0.0093(8) O2 0.0202(11) 0.0183(11) 0.0328(12) 0.0030(8) 0.0017(8) 0.0078(8) O3 0.0367(13) 0.0250(12) 0.0309(13) -0.0042(9) -0.0021(10) 0.0083(10) C14 0.0196(14) 0.0208(14) 0.0248(15) 0.0021(11) 0.0029(11) 0.0123(11) C7 0.0213(14) 0.0199(14) 0.0205(13) 0.0041(10) 0.0037(10) 0.0129(11) C13 0.0199(14) 0.0188(14) 0.0211(13) 0.0032(10) 0.0008(10) 0.0096(11) C11 0.0212(14) 0.0232(15) 0.0282(15) 0.0040(11) 0.0023(11) 0.0098(12) C1 0.0194(14) 0.0195(14) 0.0196(13) 0.0022(10) 0.0053(10) 0.0097(11) C18 0.0339(16) 0.0250(15) 0.0229(14) 0.0035(11) 0.0033(12) 0.0154(13) C12 0.0224(15) 0.0212(15) 0.0226(14) 0.0034(11) 0.0030(11) 0.0105(12) C10 0.0219(14) 0.0316(17) 0.0290(15) 0.0037(12) 0.0046(11) 0.0166(13) C17 0.0253(15) 0.0206(15) 0.0288(16) 0.0010(11) -0.0035(12) 0.0114(12) C3 0.0234(15) 0.0250(16) 0.0323(16) 0.0025(12) -0.0012(12) 0.0134(12) C16 0.0197(14) 0.0225(15) 0.0334(17) 0.0021(12) 0.0050(12) 0.0088(11) C6 0.0203(14) 0.0226(15) 0.0241(14) 0.0022(11) 0.0034(11) 0.0111(12) C2 0.0219(14) 0.0223(14) 0.0257(14) 0.0036(11) 0.0045(11) 0.0101(11) C15 0.0222(14) 0.0222(15) 0.0253(14) 0.0017(11) 0.0044(11) 0.0109(11) C8 0.0253(15) 0.0206(15) 0.0268(15) 0.0032(11) 0.0037(11) 0.0138(12) C9 0.0262(15) 0.0241(16) 0.0331(16) 0.0062(12) 0.0050(12) 0.0171(12) C19 0.0252(15) 0.0206(15) 0.0257(15) 0.0067(11) 0.0060(11) 0.0099(12) C5 0.0251(15) 0.0189(15) 0.0320(16) 0.0032(11) 0.0025(12) 0.0074(12) C4 0.0298(16) 0.0210(15) 0.0344(16) 0.0056(12) 0.0020(12) 0.0147(13) C20 0.057(2) 0.0316(18) 0.0271(17) -0.0031(13) -0.0042(15) 0.0117(17) C2G 0.0313(19) 0.080(3) 0.0325(19) 0.0056(19) 0.0054(15) 0.0077(19) C1G 0.036(2) 0.050(2) 0.047(2) 0.0044(17) 0.0163(16) 0.0030(17) C3G 0.042(2) 0.052(2) 0.052(2) 0.0167(19) 0.0151(18) 0.0181(19) C4G 0.069(3) 0.050(3) 0.086(4) -0.008(2) 0.036(3) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.448(3) . ? O1 H1 0.959(8) . ? O2 C12 1.385(3) . ? O2 C6 1.392(3) . ? O3 C17 1.375(4) . ? O3 C20 1.423(4) . ? C14 C15 1.383(4) . ? C14 C19 1.393(4) . ? C14 C13 1.532(4) . ? C7 C12 1.387(4) . ? C7 C8 1.397(4) . ? C7 C13 1.524(4) . ? C13 C1 1.520(4) . ? C11 C10 1.379(4) . ? C11 C12 1.390(4) . ? C11 H11 0.9500 . ? C1 C6 1.377(4) . ? C1 C2 1.405(4) . ? C18 C17 1.382(4) . ? C18 C19 1.391(4) . ? C18 H18 0.9500 . ? C10 C9 1.383(4) . ? C10 H10 0.9500 . ? C17 C16 1.387(4) . ? C3 C2 1.381(4) . ? C3 C4 1.394(4) . ? C3 H3 0.9500 . ? C16 C15 1.391(4) . ? C16 H16 0.9500 . ? C6 C5 1.388(4) . ? C2 H2 0.9500 . ? C15 H15 0.9500 . ? C8 C9 1.375(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C19 H19 0.9500 . ? C5 C4 1.377(4) . ? C5 H5 0.9500 . ? C4 H4 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C2G C3G 1.377(6) . ? C2G C1G 1.395(6) . ? C2G H2G 0.9500 . ? C1G C3G 1.383(6) 2 ? C1G C4G 1.497(6) . ? C3G C1G 1.383(6) 2 ? C3G H3G 0.9500 . ? C4G H4G1 0.9800 . ? C4G H4G2 0.9800 . ? C4G H4G3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 H1 111(2) . . ? C12 O2 C6 118.4(2) . . ? C17 O3 C20 116.8(3) . . ? C15 C14 C19 118.5(3) . . ? C15 C14 C13 122.5(3) . . ? C19 C14 C13 119.0(2) . . ? C12 C7 C8 117.2(3) . . ? C12 C7 C13 120.6(2) . . ? C8 C7 C13 122.0(2) . . ? O1 C13 C1 109.0(2) . . ? O1 C13 C7 108.7(2) . . ? C1 C13 C7 109.2(2) . . ? O1 C13 C14 105.9(2) . . ? C1 C13 C14 112.0(2) . . ? C7 C13 C14 111.9(2) . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C6 C1 C2 116.6(3) . . ? C6 C1 C13 122.1(2) . . ? C2 C1 C13 121.1(2) . . ? C17 C18 C19 118.7(3) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? O2 C12 C7 122.7(2) . . ? O2 C12 C11 115.3(2) . . ? C7 C12 C11 122.0(3) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? O3 C17 C18 124.3(3) . . ? O3 C17 C16 115.3(3) . . ? C18 C17 C16 120.3(3) . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C1 C6 C5 123.2(3) . . ? C1 C6 O2 121.8(2) . . ? C5 C6 O2 114.9(3) . . ? C3 C2 C1 121.2(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C9 C8 C7 121.5(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C18 C19 C14 121.8(3) . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? C4 C5 C6 119.1(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C3G C2G C1G 121.2(4) . . ? C3G C2G H2G 119.4 . . ? C1G C2G H2G 119.4 . . ? C3G C1G C2G 117.7(4) 2 . ? C3G C1G C4G 121.3(4) 2 . ? C2G C1G C4G 121.0(4) . . ? C2G C3G C1G 121.1(4) . 2 ? C2G C3G H3G 119.5 . . ? C1G C3G H3G 119.5 2 . ? C1G C4G H4G1 109.5 . . ? C1G C4G H4G2 109.5 . . ? H4G1 C4G H4G2 109.5 . . ? C1G C4G H4G3 109.5 . . ? H4G1 C4G H4G3 109.5 . . ? H4G2 C4G H4G3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C7 C13 O1 -95.8(3) . . . . ? C8 C7 C13 O1 78.1(3) . . . . ? C12 C7 C13 C1 22.9(3) . . . . ? C8 C7 C13 C1 -163.1(2) . . . . ? C12 C7 C13 C14 147.5(3) . . . . ? C8 C7 C13 C14 -38.5(3) . . . . ? C15 C14 C13 O1 2.4(3) . . . . ? C19 C14 C13 O1 -177.5(2) . . . . ? C15 C14 C13 C1 -116.3(3) . . . . ? C19 C14 C13 C1 63.8(3) . . . . ? C15 C14 C13 C7 120.7(3) . . . . ? C19 C14 C13 C7 -59.2(3) . . . . ? O1 C13 C1 C6 97.3(3) . . . . ? C7 C13 C1 C6 -21.4(3) . . . . ? C14 C13 C1 C6 -145.9(3) . . . . ? O1 C13 C1 C2 -77.0(3) . . . . ? C7 C13 C1 C2 164.4(2) . . . . ? C14 C13 C1 C2 39.8(3) . . . . ? C6 O2 C12 C7 -10.9(4) . . . . ? C6 O2 C12 C11 169.0(2) . . . . ? C8 C7 C12 O2 177.4(2) . . . . ? C13 C7 C12 O2 -8.4(4) . . . . ? C8 C7 C12 C11 -2.5(4) . . . . ? C13 C7 C12 C11 171.7(3) . . . . ? C10 C11 C12 O2 -179.3(2) . . . . ? C10 C11 C12 C7 0.6(5) . . . . ? C12 C11 C10 C9 1.8(4) . . . . ? C20 O3 C17 C18 0.9(4) . . . . ? C20 O3 C17 C16 -177.2(3) . . . . ? C19 C18 C17 O3 -178.6(2) . . . . ? C19 C18 C17 C16 -0.5(4) . . . . ? O3 C17 C16 C15 178.7(2) . . . . ? C18 C17 C16 C15 0.4(4) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? C13 C1 C6 C5 -174.8(3) . . . . ? C2 C1 C6 O2 179.3(2) . . . . ? C13 C1 C6 O2 4.7(4) . . . . ? C12 O2 C6 C1 12.8(4) . . . . ? C12 O2 C6 C5 -167.6(2) . . . . ? C4 C3 C2 C1 1.7(4) . . . . ? C6 C1 C2 C3 -0.9(4) . . . . ? C13 C1 C2 C3 173.7(3) . . . . ? C19 C14 C15 C16 -1.5(4) . . . . ? C13 C14 C15 C16 178.6(2) . . . . ? C17 C16 C15 C14 0.6(4) . . . . ? C12 C7 C8 C9 2.0(4) . . . . ? C13 C7 C8 C9 -172.1(3) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C11 C10 C9 C8 -2.3(5) . . . . ? C17 C18 C19 C14 -0.5(4) . . . . ? C15 C14 C19 C18 1.5(4) . . . . ? C13 C14 C19 C18 -178.7(2) . . . . ? C1 C6 C5 C4 0.7(5) . . . . ? O2 C6 C5 C4 -178.9(3) . . . . ? C6 C5 C4 C3 0.1(5) . . . . ? C2 C3 C4 C5 -1.3(5) . . . . ? C3G C2G C1G C3G 0.1(6) . . . 2 ? C3G C2G C1G C4G 179.8(4) . . . . ? C1G C2G C3G C1G -0.1(6) . . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.959(8) 1.925(8) 2.865(3) 166(3) 2_566 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.17 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.140 _refine_diff_density_min -0.863 _refine_diff_density_rms 0.278 data_c:\struct~1\a1pxy_~1\1c _database_code_depnum_ccdc_archive 'CCDC 239534' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate ; _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate' _chemical_formula_moiety 'C20 H16 O3.C3 H3' _chemical_formula_sum 'C23 H19 O3' _chemical_formula_weight 343.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3719(4) _cell_length_b 9.1093(5) _cell_length_c 12.6935(7) _cell_angle_alpha 97.482(2) _cell_angle_beta 103.946(2) _cell_angle_gamma 109.425(3) _cell_volume 862.30(8) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9645 _exptl_absorpt_correction_T_max 0.9812 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1.0\%, 60s per \%, 2 iterations. ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 3421 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.54 _reflns_number_total 3421 _reflns_number_gt 2744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3421 _refine_ls_number_parameters 240 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.2241 _refine_ls_R_factor_gt 0.2028 _refine_ls_wR_factor_ref 0.5249 _refine_ls_wR_factor_gt 0.5102 _refine_ls_goodness_of_fit_ref 2.409 _refine_ls_restrained_S_all 2.408 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.0409(5) 0.4981(4) 0.3818(3) 0.0194(10) Uani 1 1 d . . . O1 O -0.2893(5) 0.2084(4) 0.4670(3) 0.0194(10) Uani 1 1 d D . . C7 C -0.0647(7) 0.2128(6) 0.3760(4) 0.0171(12) Uani 1 1 d . . . C1 C -0.2755(7) 0.3447(6) 0.3171(5) 0.0189(13) Uani 1 1 d . . . C13 C -0.2559(7) 0.2029(6) 0.3595(5) 0.0186(13) Uani 1 1 d . . . O3 O -0.7803(6) -0.3788(5) 0.0701(4) 0.0294(12) Uani 1 1 d . . . C11 C 0.2474(7) 0.3742(6) 0.4200(5) 0.0208(13) Uani 1 1 d . . . H11 H 0.3392 0.4753 0.4310 0.025 Uiso 1 1 calc R . . C10 C 0.2882(7) 0.2412(6) 0.4318(5) 0.0206(13) Uani 1 1 d . . . H10 H 0.4088 0.2508 0.4513 0.025 Uiso 1 1 calc R . . C6 C -0.1338(7) 0.4858(6) 0.3351(5) 0.0173(12) Uani 1 1 d . . . C8 C -0.0181(8) 0.0811(6) 0.3870(5) 0.0200(13) Uani 1 1 d . . . H8 H -0.1091 -0.0210 0.3745 0.024 Uiso 1 1 calc R . . C16 C -0.6492(8) -0.2014(7) 0.2458(5) 0.0237(13) Uani 1 1 d . . . H16 H -0.7355 -0.2727 0.2711 0.028 Uiso 1 1 calc R . . C14 C -0.3943(7) 0.0445(6) 0.2829(5) 0.0184(13) Uani 1 1 d . . . C12 C 0.0714(8) 0.3587(6) 0.3920(5) 0.0197(13) Uani 1 1 d . . . C5 C -0.1488(8) 0.6246(6) 0.3076(5) 0.0232(13) Uani 1 1 d . . . H5 H -0.0460 0.7185 0.3212 0.028 Uiso 1 1 calc R . . C18 C -0.5189(8) -0.1362(7) 0.0989(5) 0.0238(13) Uani 1 1 d . . . H18 H -0.5163 -0.1622 0.0246 0.029 Uiso 1 1 calc R . . C9 C 0.1554(7) 0.0954(7) 0.4154(5) 0.0242(14) Uani 1 1 d . . . H9 H 0.1840 0.0042 0.4239 0.029 Uiso 1 1 calc R . . C4 C -0.3146(8) 0.6230(7) 0.2607(5) 0.0244(14) Uani 1 1 d . . . H4 H -0.3280 0.7173 0.2430 0.029 Uiso 1 1 calc R . . C17 C -0.6503(7) -0.2385(6) 0.1363(5) 0.0196(13) Uani 1 1 d . . . C15 C -0.5225(7) -0.0603(7) 0.3195(5) 0.0220(13) Uani 1 1 d . . . H15 H -0.5236 -0.0358 0.3944 0.026 Uiso 1 1 calc R . . C2 C -0.4442(8) 0.3462(7) 0.2670(5) 0.0224(13) Uani 1 1 d . . . H2 H -0.5468 0.2518 0.2522 0.027 Uiso 1 1 calc R . . C19 C -0.3938(7) 0.0028(7) 0.1729(5) 0.0214(13) Uani 1 1 d . . . H19 H -0.3049 0.0722 0.1482 0.026 Uiso 1 1 calc R . . C3 C -0.4638(8) 0.4833(7) 0.2386(5) 0.0269(14) Uani 1 1 d . . . H3 H -0.5788 0.4816 0.2044 0.032 Uiso 1 1 calc R . . C20 C -0.7896(10) -0.4193(8) -0.0433(6) 0.0431(19) Uani 1 1 d . . . H20A H -0.7990 -0.3319 -0.0787 0.065 Uiso 1 1 calc R . . H20B H -0.8942 -0.5172 -0.0816 0.065 Uiso 1 1 calc R . . H20C H -0.6821 -0.4369 -0.0482 0.065 Uiso 1 1 calc R . . C2G C 0.0554(9) 0.0847(9) 0.1080(6) 0.0435(19) Uani 1 1 d . . . H2G H 0.0957 0.1435 0.1832 0.052 Uiso 1 1 calc R . . C3G C -0.0159(11) -0.0776(11) 0.0841(7) 0.052(2) Uani 1 1 d . . . H3G H -0.0290 -0.1318 0.1424 0.062 Uiso 1 1 calc R . . C1G C 0.0692(12) 0.1637(10) 0.0236(8) 0.058(2) Uani 1 1 d . . . H1G H 0.1155 0.2773 0.0397 0.070 Uiso 1 1 calc R . . H1 H -0.207(6) 0.304(4) 0.521(3) 0.014(14) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.020(2) 0.0124(19) 0.028(2) 0.0047(16) 0.0073(17) 0.0088(16) O1 0.021(2) 0.023(2) 0.019(2) 0.0059(16) 0.0089(17) 0.0125(17) C7 0.025(3) 0.015(3) 0.016(3) 0.000(2) 0.010(2) 0.011(2) C1 0.029(3) 0.013(3) 0.020(3) 0.005(2) 0.012(2) 0.012(2) C13 0.026(3) 0.017(3) 0.022(3) 0.008(2) 0.012(2) 0.015(2) O3 0.030(2) 0.023(2) 0.031(3) 0.0009(19) 0.009(2) 0.0073(19) C11 0.021(3) 0.017(3) 0.022(3) 0.002(2) 0.005(2) 0.007(2) C10 0.019(3) 0.024(3) 0.022(3) 0.003(2) 0.005(2) 0.014(2) C6 0.015(3) 0.018(3) 0.019(3) 0.001(2) 0.008(2) 0.007(2) C8 0.028(3) 0.018(3) 0.021(3) 0.007(2) 0.009(2) 0.015(2) C16 0.023(3) 0.020(3) 0.034(3) 0.012(2) 0.015(3) 0.010(2) C14 0.021(3) 0.021(3) 0.023(3) 0.008(2) 0.010(2) 0.016(2) C12 0.027(3) 0.016(3) 0.021(3) 0.009(2) 0.006(2) 0.015(2) C5 0.029(3) 0.014(3) 0.023(3) 0.000(2) 0.009(3) 0.004(2) C18 0.024(3) 0.026(3) 0.024(3) 0.009(2) 0.007(2) 0.011(2) C9 0.024(3) 0.026(3) 0.030(3) 0.007(2) 0.008(2) 0.018(3) C4 0.033(3) 0.018(3) 0.028(3) 0.007(2) 0.009(3) 0.017(2) C17 0.019(3) 0.018(3) 0.023(3) 0.004(2) 0.003(2) 0.011(2) C15 0.020(3) 0.024(3) 0.028(3) 0.007(2) 0.009(2) 0.015(2) C2 0.023(3) 0.019(3) 0.031(3) 0.007(2) 0.013(2) 0.012(2) C19 0.023(3) 0.022(3) 0.026(3) 0.009(2) 0.014(2) 0.012(2) C3 0.028(3) 0.029(3) 0.031(3) 0.010(3) 0.010(3) 0.017(3) C20 0.046(4) 0.033(4) 0.033(4) 0.001(3) 0.010(3) -0.002(3) C2G 0.037(4) 0.053(5) 0.031(4) 0.003(3) 0.008(3) 0.011(3) C3G 0.050(5) 0.067(6) 0.040(4) 0.017(4) 0.016(4) 0.020(4) C1G 0.064(6) 0.038(4) 0.066(6) 0.005(4) 0.019(5) 0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C12 1.391(6) . ? O2 C6 1.400(6) . ? O1 C13 1.455(6) . ? O1 H1 0.963(8) . ? C7 C12 1.384(8) . ? C7 C8 1.392(7) . ? C7 C13 1.534(7) . ? C1 C6 1.375(8) . ? C1 C2 1.407(8) . ? C1 C13 1.505(7) . ? C13 C14 1.533(8) . ? O3 C17 1.370(7) . ? O3 C20 1.415(8) . ? C11 C10 1.380(8) . ? C11 C12 1.384(8) . ? C11 H11 0.9500 . ? C10 C9 1.371(8) . ? C10 H10 0.9500 . ? C6 C5 1.391(8) . ? C8 C9 1.366(7) . ? C8 H8 0.9500 . ? C16 C17 1.384(8) . ? C16 C15 1.398(8) . ? C16 H16 0.9500 . ? C14 C15 1.398(8) . ? C14 C19 1.400(8) . ? C5 C4 1.366(8) . ? C5 H5 0.9500 . ? C18 C19 1.385(8) . ? C18 C17 1.410(8) . ? C18 H18 0.9500 . ? C9 H9 0.9500 . ? C4 C3 1.393(9) . ? C4 H4 0.9500 . ? C15 H15 0.9500 . ? C2 C3 1.393(8) . ? C2 H2 0.9500 . ? C19 H19 0.9500 . ? C3 H3 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C2G C3G 1.357(11) . ? C2G C1G 1.373(12) . ? C2G H2G 0.9500 . ? C3G C1G 1.370(12) 2 ? C3G H3G 0.9500 . ? C1G C3G 1.370(12) 2 ? C1G H1G 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O2 C6 118.5(4) . . ? C13 O1 H1 111(3) . . ? C12 C7 C8 117.5(5) . . ? C12 C7 C13 120.2(5) . . ? C8 C7 C13 121.9(5) . . ? C6 C1 C2 115.7(5) . . ? C6 C1 C13 122.7(5) . . ? C2 C1 C13 121.3(5) . . ? O1 C13 C1 108.9(4) . . ? O1 C13 C14 105.9(4) . . ? C1 C13 C14 111.8(4) . . ? O1 C13 C7 108.4(4) . . ? C1 C13 C7 109.1(4) . . ? C14 C13 C7 112.5(4) . . ? C17 O3 C20 118.5(5) . . ? C10 C11 C12 119.3(5) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.4 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C1 C6 C5 124.4(5) . . ? C1 C6 O2 121.0(5) . . ? C5 C6 O2 114.6(5) . . ? C9 C8 C7 121.5(5) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.2 . . ? C17 C16 C15 120.8(5) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C15 C14 C19 118.6(5) . . ? C15 C14 C13 121.9(5) . . ? C19 C14 C13 119.5(5) . . ? C11 C12 C7 121.4(5) . . ? C11 C12 O2 115.9(5) . . ? C7 C12 O2 122.6(5) . . ? C4 C5 C6 118.6(5) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C19 C18 C17 118.6(5) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C8 C9 C10 120.1(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? O3 C17 C16 116.6(5) . . ? O3 C17 C18 123.4(5) . . ? C16 C17 C18 120.0(5) . . ? C14 C15 C16 119.8(5) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C3 C2 C1 121.4(5) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C18 C19 C14 122.0(5) . . ? C18 C19 H19 119.0 . . ? C14 C19 H19 119.0 . . ? C4 C3 C2 119.9(6) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C3G C2G C1G 120.0(7) . . ? C3G C2G H2G 120.0 . . ? C1G C2G H2G 120.0 . . ? C2G C3G C1G 120.5(8) . 2 ? C2G C3G H3G 119.8 . . ? C1G C3G H3G 119.8 2 . ? C3G C1G C2G 119.5(8) 2 . ? C3G C1G H1G 120.2 2 . ? C2G C1G H1G 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C13 O1 94.0(6) . . . . ? C2 C1 C13 O1 -78.8(6) . . . . ? C6 C1 C13 C14 -149.4(5) . . . . ? C2 C1 C13 C14 37.8(7) . . . . ? C6 C1 C13 C7 -24.2(7) . . . . ? C2 C1 C13 C7 163.0(5) . . . . ? C12 C7 C13 O1 -95.2(6) . . . . ? C8 C7 C13 O1 78.1(6) . . . . ? C12 C7 C13 C1 23.3(7) . . . . ? C8 C7 C13 C1 -163.4(5) . . . . ? C12 C7 C13 C14 148.1(5) . . . . ? C8 C7 C13 C14 -38.7(7) . . . . ? C12 C11 C10 C9 0.3(9) . . . . ? C2 C1 C6 C5 0.2(8) . . . . ? C13 C1 C6 C5 -172.9(5) . . . . ? C2 C1 C6 O2 -178.4(4) . . . . ? C13 C1 C6 O2 8.4(8) . . . . ? C12 O2 C6 C1 11.0(7) . . . . ? C12 O2 C6 C5 -167.8(5) . . . . ? C12 C7 C8 C9 1.7(8) . . . . ? C13 C7 C8 C9 -171.8(5) . . . . ? O1 C13 C14 C15 1.6(6) . . . . ? C1 C13 C14 C15 -116.9(5) . . . . ? C7 C13 C14 C15 119.8(5) . . . . ? O1 C13 C14 C19 -178.7(4) . . . . ? C1 C13 C14 C19 62.8(6) . . . . ? C7 C13 C14 C19 -60.4(6) . . . . ? C10 C11 C12 C7 0.3(9) . . . . ? C10 C11 C12 O2 179.9(5) . . . . ? C8 C7 C12 C11 -1.2(8) . . . . ? C13 C7 C12 C11 172.3(5) . . . . ? C8 C7 C12 O2 179.2(5) . . . . ? C13 C7 C12 O2 -7.2(8) . . . . ? C6 O2 C12 C11 169.0(5) . . . . ? C6 O2 C12 C7 -11.4(8) . . . . ? C1 C6 C5 C4 0.8(9) . . . . ? O2 C6 C5 C4 179.5(5) . . . . ? C7 C8 C9 C10 -1.2(9) . . . . ? C11 C10 C9 C8 0.2(9) . . . . ? C6 C5 C4 C3 -1.6(9) . . . . ? C20 O3 C17 C16 178.2(5) . . . . ? C20 O3 C17 C18 -3.6(8) . . . . ? C15 C16 C17 O3 -179.5(5) . . . . ? C15 C16 C17 C18 2.2(8) . . . . ? C19 C18 C17 O3 179.9(5) . . . . ? C19 C18 C17 C16 -1.9(8) . . . . ? C19 C14 C15 C16 -1.5(8) . . . . ? C13 C14 C15 C16 178.2(5) . . . . ? C17 C16 C15 C14 -0.5(8) . . . . ? C6 C1 C2 C3 -0.4(8) . . . . ? C13 C1 C2 C3 172.9(5) . . . . ? C17 C18 C19 C14 -0.1(8) . . . . ? C15 C14 C19 C18 1.8(8) . . . . ? C13 C14 C19 C18 -177.9(5) . . . . ? C5 C4 C3 C2 1.5(9) . . . . ? C1 C2 C3 C4 -0.5(9) . . . . ? C1G C2G C3G C1G 2.1(14) . . . 2 ? C3G C2G C1G C3G -2.1(14) . . . 2 ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 26.54 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 2.167 _refine_diff_density_min -1.350 _refine_diff_density_rms 0.337 data_1d _database_code_depnum_ccdc_archive 'CCDC 239535' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate ; _chemical_formula_moiety 'C20 H16 O3.C3 H3' _chemical_formula_sum 'C23 H19 O3' _chemical_formula_weight 343.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.37630(10) _cell_length_b 9.0965(2) _cell_length_c 12.6943(3) _cell_angle_alpha 97.4850(10) _cell_angle_beta 104.1640(10) _cell_angle_gamma 109.3880(10) _cell_volume 860.68(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description Cuboid _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 0.9811 _exptl_special_details ; "Complete sphere of data collected using COLLECT strategy (Nonius, 2000)." Crystal to detector distance = 40mm; combination of \f and \w scans of "1.0\%, 55s per \%, 2 iterations." ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 3760 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.15 _reflns_number_total 3760 _reflns_number_gt 2827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and "goodness of fit S are based on F^2^, conventional R-factors R are based" "on F, with F set to zero for negative F^2^. The threshold expression of" F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based "on F^2^ are statistically about twice as large as those based on F, and R-" factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1444P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3760 _refine_ls_number_parameters 240 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.2044 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.28905(16) 0.20785(14) 0.46648(9) 0.0158(3) Uani 1 1 d D . . H1 H -0.202(3) 0.3083(17) 0.5119(17) 0.053(8) Uiso 1 1 d D . . O2 O 0.04041(16) 0.49751(14) 0.38198(10) 0.0174(3) Uani 1 1 d . . . H2 H -0.5492 0.2498 0.2479 0.022 Uiso 1 1 calc R . . O3 O -0.78248(17) -0.37923(15) 0.07014(10) 0.0225(4) Uani 1 1 d . . . C1 C -0.2785(2) 0.3447(2) 0.31624(14) 0.0148(4) Uani 1 1 d . . . C2 C -0.4469(2) 0.3453(2) 0.26478(16) 0.0187(4) Uani 1 1 d . . . C3 C -0.4670(3) 0.4820(2) 0.23825(16) 0.0224(5) Uani 1 1 d . . . H3 H -0.5822 0.4803 0.2042 0.027 Uiso 1 1 calc R . . C4 C -0.3178(3) 0.6224(2) 0.26147(16) 0.0209(4) Uani 1 1 d . . . H4 H -0.3314 0.7172 0.2447 0.025 Uiso 1 1 calc R . . C5 C -0.1503(3) 0.6237(2) 0.30885(15) 0.0188(4) Uani 1 1 d . . . H5 H -0.0479 0.7184 0.3233 0.023 Uiso 1 1 calc R . . C6 C -0.1329(2) 0.4850(2) 0.33519(14) 0.0150(4) Uani 1 1 d . . . C7 C -0.0665(2) 0.2123(2) 0.37574(14) 0.0136(4) Uani 1 1 d . . . C8 C -0.0202(2) 0.0804(2) 0.38718(15) 0.0170(4) Uani 1 1 d . . . H8 H -0.1113 -0.0214 0.3756 0.020 Uiso 1 1 calc R . . C9 C 0.1561(2) 0.0942(2) 0.41511(15) 0.0186(4) Uani 1 1 d . . . H9 H 0.1847 0.0027 0.4228 0.022 Uiso 1 1 calc R . . C10 C 0.2901(2) 0.2423(2) 0.43169(15) 0.0196(4) Uani 1 1 d . . . H10 H 0.4110 0.2528 0.4522 0.023 Uiso 1 1 calc R . . C11 C 0.2475(2) 0.3742(2) 0.41826(15) 0.0185(4) Uani 1 1 d . . . H11 H 0.3384 0.4753 0.4275 0.022 Uiso 1 1 calc R . . C12 C 0.0703(2) 0.3579(2) 0.39107(14) 0.0145(4) Uani 1 1 d . . . C13 C -0.2565(2) 0.2018(2) 0.35904(14) 0.0143(4) Uani 1 1 d . . . C14 C -0.3941(2) 0.0431(2) 0.28244(14) 0.0140(4) Uani 1 1 d . . . C15 C -0.5226(2) -0.0612(2) 0.31847(15) 0.0168(4) Uani 1 1 d . . . H15 H -0.5231 -0.0363 0.3934 0.020 Uiso 1 1 calc R . . C16 C -0.6499(2) -0.2012(2) 0.24535(16) 0.0186(4) Uani 1 1 d . . . H16 H -0.7367 -0.2720 0.2706 0.022 Uiso 1 1 calc R . . C17 C -0.6509(2) -0.2384(2) 0.13550(15) 0.0166(4) Uani 1 1 d . . . C18 C -0.5210(2) -0.1371(2) 0.09900(15) 0.0180(4) Uani 1 1 d . . . H18 H -0.5192 -0.1631 0.0245 0.022 Uiso 1 1 calc R . . C19 C -0.3943(2) 0.0024(2) 0.17294(15) 0.0169(4) Uani 1 1 d . . . H19 H -0.3056 0.0716 0.1482 0.020 Uiso 1 1 calc R . . C20 C -0.7928(3) -0.4178(3) -0.04425(17) 0.0346(6) Uani 1 1 d . . . H20A H -0.8016 -0.3290 -0.0784 0.052 Uiso 1 1 calc R . . H20B H -0.8980 -0.5151 -0.0833 0.052 Uiso 1 1 calc R . . H20C H -0.6858 -0.4358 -0.0498 0.052 Uiso 1 1 calc R . . C1G C 0.0158(3) 0.0777(3) -0.08528(19) 0.0390(6) Uani 1 1 d . . . H1G H 0.0273 0.1319 -0.1438 0.047 Uiso 1 1 calc R . . C2G C -0.0548(3) -0.0865(3) -0.10913(18) 0.0341(6) Uani 1 1 d . . . H2G H -0.0928 -0.1459 -0.1841 0.041 Uiso 1 1 calc R . . C3G C -0.0707(3) -0.1650(3) -0.0242(2) 0.0403(6) Uani 1 1 d . . . H3G H -0.1191 -0.2788 -0.0404 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0170(7) 0.0161(7) 0.0143(7) 0.0029(5) 0.0064(5) 0.0055(5) O2 0.0138(7) 0.0115(7) 0.0241(7) 0.0030(5) 0.0027(5) 0.0040(5) O3 0.0212(7) 0.0176(7) 0.0192(7) 0.0000(5) 0.0045(6) -0.0017(6) C1 0.0165(9) 0.0134(9) 0.0160(9) 0.0033(7) 0.0070(7) 0.0061(7) C2 0.0175(10) 0.0173(9) 0.0224(10) 0.0061(7) 0.0063(8) 0.0071(8) C3 0.0190(10) 0.0230(11) 0.0278(10) 0.0077(8) 0.0060(8) 0.0112(8) C4 0.0250(10) 0.0174(10) 0.0246(10) 0.0070(8) 0.0075(8) 0.0128(8) C5 0.0222(10) 0.0131(9) 0.0206(9) 0.0037(7) 0.0067(8) 0.0062(8) C6 0.0143(9) 0.0163(9) 0.0149(8) 0.0027(7) 0.0040(7) 0.0070(7) C7 0.0136(9) 0.0152(9) 0.0122(8) 0.0027(7) 0.0039(7) 0.0059(7) C8 0.0169(10) 0.0150(9) 0.0202(9) 0.0049(7) 0.0063(7) 0.0066(7) C9 0.0196(10) 0.0187(10) 0.0209(10) 0.0054(7) 0.0069(8) 0.0106(8) C10 0.0153(9) 0.0252(10) 0.0206(9) 0.0045(8) 0.0062(7) 0.0104(8) C11 0.0151(9) 0.0180(10) 0.0194(9) 0.0018(7) 0.0046(7) 0.0040(8) C12 0.0164(9) 0.0133(9) 0.0142(8) 0.0023(7) 0.0048(7) 0.0065(7) C13 0.0144(9) 0.0141(9) 0.0159(9) 0.0048(7) 0.0065(7) 0.0054(7) C14 0.0137(9) 0.0140(9) 0.0165(9) 0.0044(7) 0.0045(7) 0.0077(7) C15 0.0156(9) 0.0169(9) 0.0190(9) 0.0036(7) 0.0064(7) 0.0069(7) C16 0.0151(9) 0.0170(10) 0.0237(10) 0.0062(7) 0.0083(8) 0.0040(7) C17 0.0136(9) 0.0135(9) 0.0195(9) 0.0015(7) 0.0021(7) 0.0041(7) C18 0.0204(10) 0.0170(9) 0.0153(9) 0.0038(7) 0.0047(7) 0.0059(8) C19 0.0176(9) 0.0149(9) 0.0191(9) 0.0068(7) 0.0067(7) 0.0056(7) C20 0.0313(12) 0.0331(13) 0.0209(11) -0.0062(9) 0.0082(9) -0.0064(10) C1G 0.0446(15) 0.0465(15) 0.0278(12) 0.0183(10) 0.0118(11) 0.0155(12) C2G 0.0321(13) 0.0407(14) 0.0241(11) 0.0012(9) 0.0061(9) 0.0111(11) C3G 0.0444(15) 0.0308(13) 0.0394(14) 0.0067(10) 0.0107(11) 0.0086(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken "into account individually in the estimation of esds in distances, angles" and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4525(19) . ? O1 H1 0.955(7) . ? O2 C12 1.387(2) . ? O2 C6 1.387(2) . ? O3 C17 1.372(2) . ? O3 C20 1.423(2) . ? C1 C2 1.404(3) . ? C1 C6 1.384(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C3 1.393(3) . ? C4 H4 0.9500 . ? C5 C4 1.380(3) . ? C5 C6 1.391(2) . ? C5 H5 0.9500 . ? C7 C12 1.386(3) . ? C7 C8 1.392(2) . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.381(3) . ? C10 C9 1.388(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C11 1.391(3) . ? C13 C1 1.521(2) . ? C13 C7 1.522(2) . ? C14 C13 1.530(2) . ? C14 C15 1.394(2) . ? C14 C19 1.391(2) . ? C15 H15 0.9500 . ? C16 C15 1.388(3) . ? C16 C17 1.389(3) . ? C16 H16 0.9500 . ? C17 C18 1.393(2) . ? C18 H18 0.9500 . ? C19 C18 1.388(3) . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C1G C3G 1.389(3) 2 ? C1G H1G 0.9500 . ? C2G C1G 1.371(3) . ? C2G C3G 1.378(3) . ? C2G H2G 0.9500 . ? C3G C1G 1.389(3) 2 ? C3G H3G 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C13 C1 108.49(13) . . ? O1 C13 C14 106.14(13) . . ? O1 C13 C7 108.33(13) . . ? O2 C12 C11 115.43(15) . . ? O2 C6 C5 115.20(15) . . ? O3 C17 C16 115.67(16) . . ? O3 C17 C18 124.30(16) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? C1 C13 C14 111.75(14) . . ? C1 C13 C7 109.52(14) . . ? C1 C2 H2 119.3 . . ? C1 C6 C5 122.26(17) . . ? C1 C6 O2 122.54(16) . . ? C2 C1 C13 121.81(15) . . ? C2 C3 C4 119.83(18) . . ? C2 C3 H3 120.1 . . ? C3 C2 C1 121.38(17) . . ? C3 C2 H2 119.3 . . ? C3 C4 H4 120.0 . . ? C4 C3 H3 120.1 . . ? C4 C5 C6 119.32(17) . . ? C4 C5 H5 120.3 . . ? C5 C4 C3 119.95(17) . . ? C5 C4 H4 120.0 . . ? C6 C1 C13 120.79(16) . . ? C6 C1 C2 117.19(16) . . ? C6 C5 H5 120.3 . . ? C7 C12 C11 122.11(16) . . ? C7 C12 O2 122.46(16) . . ? C7 C13 C14 112.43(14) . . ? C7 C8 H8 119.2 . . ? C8 C7 C13 121.61(15) . . ? C8 C9 H9 120.1 . . ? C9 C10 H10 120.1 . . ? C9 C8 C7 121.58(17) . . ? C9 C8 H8 119.2 . . ? C10 C11 C12 119.44(17) . . ? C10 C11 H11 120.3 . . ? C10 C9 C8 119.70(17) . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 119.88(17) . . ? C11 C10 H10 120.1 . . ? C12 C11 H11 120.3 . . ? C12 C7 C13 120.82(15) . . ? C12 C7 C8 117.27(16) . . ? C12 O2 C6 118.19(14) . . ? C13 O1 H1 104.0(15) . . ? C14 C15 H15 119.9 . . ? C14 C19 H19 119.2 . . ? C15 C14 C13 121.85(15) . . ? C15 C16 C17 120.32(17) . . ? C15 C16 H16 119.8 . . ? C16 C15 C14 120.30(17) . . ? C16 C15 H15 119.9 . . ? C16 C17 C18 120.01(16) . . ? C17 C16 H16 119.8 . . ? C17 C18 H18 120.4 . . ? C17 O3 C20 117.28(14) . . ? C18 C19 C14 121.50(17) . . ? C18 C19 H19 119.2 . . ? C19 C14 C13 119.41(15) . . ? C19 C14 C15 118.73(16) . . ? C19 C18 C17 119.12(17) . . ? C19 C18 H18 120.4 . . ? C1G C2G C3G 119.9(2) . . ? C1G C2G H2G 120.1 . . ? C1G C3G H3G 120.0 2 . ? C2G C1G C3G 120.2(2) . 2 ? C2G C1G H1G 119.9 . . ? C2G C3G C1G 119.9(2) . 2 ? C2G C3G H3G 120.0 . . ? C3G C1G H1G 119.9 2 . ? C3G C2G H2G 120.1 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C13 C1 C2 -79.8(2) . . . . ? O1 C13 C1 C6 94.69(18) . . . . ? O1 C13 C7 C12 -95.49(18) . . . . ? O1 C13 C7 C8 78.12(19) . . . . ? O2 C12 C11 C10 178.47(14) . . . . ? O3 C17 C18 C19 -179.88(16) . . . . ? C1 C13 C7 C12 22.7(2) . . . . ? C1 C13 C7 C8 -163.72(15) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C1 C6 C5 2.4(3) . . . . ? C2 C1 C6 O2 -177.81(15) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C4 C5 C6 O2 179.72(16) . . . . ? C5 C4 C3 C2 1.3(3) . . . . ? C6 C1 C2 C3 -2.5(3) . . . . ? C6 C5 C4 C3 -1.4(3) . . . . ? C6 O2 C12 C11 168.19(14) . . . . ? C6 O2 C12 C7 -12.7(2) . . . . ? C7 C12 C11 C10 -0.6(3) . . . . ? C7 C13 C1 C2 162.16(15) . . . . ? C7 C13 C1 C6 -23.4(2) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C7 C12 C11 -0.8(3) . . . . ? C8 C7 C12 O2 -179.90(14) . . . . ? C9 C10 C11 C12 1.7(3) . . . . ? C11 C10 C9 C8 -1.2(3) . . . . ? C12 C7 C8 C9 1.3(3) . . . . ? C12 O2 C6 C1 12.0(2) . . . . ? C12 O2 C6 C5 -168.20(14) . . . . ? C13 C1 C2 C3 172.15(16) . . . . ? C13 C1 C6 C5 -172.35(15) . . . . ? C13 C1 C6 O2 7.5(3) . . . . ? C13 C14 C15 C16 177.39(16) . . . . ? C13 C14 C19 C18 -177.27(16) . . . . ? C13 C7 C12 C11 173.03(15) . . . . ? C13 C7 C12 O2 -6.0(3) . . . . ? C13 C7 C8 C9 -172.51(16) . . . . ? C14 C13 C1 C2 36.9(2) . . . . ? C14 C13 C1 C6 -148.63(16) . . . . ? C14 C13 C7 C12 147.54(16) . . . . ? C14 C13 C7 C8 -38.8(2) . . . . ? C14 C19 C18 C17 0.0(3) . . . . ? C15 C14 C13 C1 -115.84(17) . . . . ? C15 C14 C13 C7 120.52(17) . . . . ? C15 C14 C13 O1 2.3(2) . . . . ? C15 C14 C19 C18 1.4(3) . . . . ? C15 C16 C17 C18 1.7(3) . . . . ? C15 C16 C17 O3 -179.83(15) . . . . ? C16 C17 C18 C19 -1.6(3) . . . . ? C17 C16 C15 C14 -0.3(3) . . . . ? C19 C14 C13 C1 62.7(2) . . . . ? C19 C14 C13 C7 -60.9(2) . . . . ? C19 C14 C13 O1 -179.15(14) . . . . ? C19 C14 C15 C16 -1.2(3) . . . . ? C20 O3 C17 C16 177.24(17) . . . . ? C20 O3 C17 C18 -4.4(3) . . . . ? C1G C2G C3G C1G 0.3(4) . . . 2 ? C3G C2G C1G C3G -0.3(4) . . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.955(7) 1.915(7) 2.8655(16) 173(2) 2_566 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.907 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.311 _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate' data_c:\struct~1\a1benzen\a1benzen _database_code_depnum_ccdc_archive 'CCDC 253840' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate ; _chemical_formula_moiety 'C20 H16 O3.C3 H3' _chemical_formula_sum 'C23 H19 O3' _chemical_formula_weight 343.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.37570(10) _cell_length_b 9.10040(10) _cell_length_c 12.6928(2) _cell_angle_alpha 97.5410(10) _cell_angle_beta 104.0530(10) _cell_angle_gamma 109.4050(10) _cell_volume 861.135(19) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9744 _exptl_special_details ; "Complete sphere of data collected using COLLECT strategy (Nonius, 2000)." Crystal to detector distance = 40mm; combination of \f and \w scans of "1.0\%, 55s per \%, 2 iterations." ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 7360 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3932 _reflns_number_gt 3323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and "goodness of fit S are based on F^2^, conventional R-factors R are based" "on F, with F set to zero for negative F^2^. The threshold expression of" F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based "on F^2^ are statistically about twice as large as those based on F, and R-" factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.2666P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3932 _refine_ls_number_parameters 240 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.28900(10) 0.20799(9) 0.46642(6) 0.01629(18) Uani 1 1 d D . . H1 H -0.2041(18) 0.3060(13) 0.5149(12) 0.043(5) Uiso 1 1 d D . . O2 O 0.04079(10) 0.49768(9) 0.38176(7) 0.01771(19) Uani 1 1 d . . . H2 H -0.1110 -0.0222 0.3757 0.021 Uiso 1 1 calc R . . O3 O -0.78200(11) -0.37959(10) 0.07044(7) 0.0236(2) Uani 1 1 d . . . H3 H 0.1847 0.0027 0.4231 0.023 Uiso 1 1 calc R . . C1 C -0.06645(14) 0.21222(13) 0.37570(9) 0.0144(2) Uani 1 1 d . . . C2 C -0.02002(15) 0.07973(14) 0.38725(9) 0.0175(2) Uani 1 1 d . . . C3 C 0.15589(16) 0.09406(14) 0.41518(10) 0.0191(2) Uani 1 1 d . . . C3G C -0.0153(2) -0.0784(2) 0.08491(13) 0.0405(4) Uani 1 1 d . . . C4 C 0.29037(15) 0.24250(14) 0.43158(10) 0.0195(2) Uani 1 1 d . . . H4 H 0.4111 0.2528 0.4519 0.023 Uiso 1 1 calc R . . C5 C 0.24830(15) 0.37493(14) 0.41839(10) 0.0186(2) Uani 1 1 d . . . H5 H 0.3392 0.4761 0.4279 0.022 Uiso 1 1 calc R . . C6 C 0.07082(15) 0.35799(13) 0.39101(9) 0.0150(2) Uani 1 1 d . . . C7 C -0.27835(15) 0.34444(13) 0.31604(9) 0.0151(2) Uani 1 1 d . . . C8 C -0.44643(15) 0.34484(14) 0.26474(10) 0.0193(2) Uani 1 1 d . . . H8 H -0.5487 0.2493 0.2479 0.023 Uiso 1 1 calc R . . C9 C -0.46628(16) 0.48196(15) 0.23819(10) 0.0225(3) Uani 1 1 d . . . H9 H -0.5814 0.4802 0.2042 0.027 Uiso 1 1 calc R . . C10 C -0.31717(17) 0.62240(14) 0.26143(10) 0.0218(3) Uani 1 1 d . . . H10 H -0.3308 0.7171 0.2446 0.026 Uiso 1 1 calc R . . C11 C -0.14970(16) 0.62405(14) 0.30885(10) 0.0190(2) Uani 1 1 d . . . H11 H -0.0474 0.7189 0.3236 0.023 Uiso 1 1 calc R . . C12 C -0.13247(15) 0.48493(13) 0.33487(9) 0.0156(2) Uani 1 1 d . . . C13 C -0.25639(14) 0.20148(13) 0.35915(9) 0.0140(2) Uani 1 1 d . . . C14 C -0.39349(14) 0.04324(13) 0.28271(9) 0.0142(2) Uani 1 1 d . . . C15 C -0.52224(15) -0.06129(14) 0.31854(9) 0.0171(2) Uani 1 1 d . . . H15 H -0.5228 -0.0365 0.3935 0.021 Uiso 1 1 calc R . . C16 C -0.64949(15) -0.20121(14) 0.24551(10) 0.0187(2) Uani 1 1 d . . . H16 H -0.7365 -0.2717 0.2708 0.022 Uiso 1 1 calc R . . C17 C -0.65040(15) -0.23875(13) 0.13581(9) 0.0175(2) Uani 1 1 d . . . C18 C -0.52092(16) -0.13737(14) 0.09903(9) 0.0190(2) Uani 1 1 d . . . H18 H -0.5193 -0.1633 0.0244 0.023 Uiso 1 1 calc R . . C19 C -0.39380(15) 0.00256(13) 0.17325(9) 0.0173(2) Uani 1 1 d . . . H19 H -0.3052 0.0719 0.1484 0.021 Uiso 1 1 calc R . . C20 C -0.7926(2) -0.41786(18) -0.04413(11) 0.0360(3) Uani 1 1 d . . . H20A H -0.8045 -0.3302 -0.0785 0.054 Uiso 1 1 calc R . . H20B H -0.8962 -0.5166 -0.0828 0.054 Uiso 1 1 calc R . . H20C H -0.6843 -0.4332 -0.0500 0.054 Uiso 1 1 calc R . . C1G C 0.0702(2) 0.16483(19) 0.02426(14) 0.0420(4) Uani 1 1 d . . . H1G H 0.1181 0.2786 0.0406 0.050 Uiso 1 1 calc R . . C2G C 0.05545(19) 0.08652(19) 0.10915(12) 0.0348(3) Uani 1 1 d . . . H2G H 0.0939 0.1459 0.1842 0.042 Uiso 1 1 calc R . . H3G H -0.0265 -0.1329 0.1433 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0175(4) 0.0154(4) 0.0150(4) 0.0022(3) 0.0062(3) 0.0047(3) O2 0.0142(4) 0.0117(4) 0.0245(4) 0.0028(3) 0.0028(3) 0.0043(3) O3 0.0220(4) 0.0182(4) 0.0207(4) -0.0006(3) 0.0045(3) -0.0013(4) C1 0.0144(5) 0.0148(5) 0.0136(5) 0.0025(4) 0.0038(4) 0.0058(4) C2 0.0179(6) 0.0150(5) 0.0196(5) 0.0043(4) 0.0053(4) 0.0065(5) C3 0.0208(6) 0.0188(6) 0.0213(6) 0.0052(4) 0.0066(5) 0.0115(5) C4 0.0154(5) 0.0233(6) 0.0207(6) 0.0033(5) 0.0048(4) 0.0094(5) C5 0.0152(5) 0.0173(6) 0.0207(6) 0.0020(4) 0.0052(4) 0.0042(4) C6 0.0171(5) 0.0131(5) 0.0147(5) 0.0016(4) 0.0042(4) 0.0069(4) C7 0.0164(5) 0.0137(5) 0.0160(5) 0.0025(4) 0.0057(4) 0.0066(4) C8 0.0169(6) 0.0180(6) 0.0231(6) 0.0057(4) 0.0058(4) 0.0067(5) C9 0.0196(6) 0.0226(6) 0.0270(6) 0.0071(5) 0.0050(5) 0.0111(5) C10 0.0265(6) 0.0173(6) 0.0256(6) 0.0069(5) 0.0073(5) 0.0129(5) C11 0.0219(6) 0.0132(5) 0.0207(5) 0.0036(4) 0.0062(5) 0.0057(5) C12 0.0151(5) 0.0157(5) 0.0153(5) 0.0017(4) 0.0033(4) 0.0067(4) C13 0.0142(5) 0.0135(5) 0.0151(5) 0.0036(4) 0.0054(4) 0.0054(4) C14 0.0132(5) 0.0128(5) 0.0169(5) 0.0033(4) 0.0029(4) 0.0063(4) C15 0.0170(5) 0.0169(5) 0.0180(5) 0.0036(4) 0.0063(4) 0.0066(4) C16 0.0165(5) 0.0165(6) 0.0230(6) 0.0057(4) 0.0080(4) 0.0043(5) C17 0.0151(5) 0.0139(5) 0.0203(6) 0.0022(4) 0.0021(4) 0.0044(4) C18 0.0213(6) 0.0185(6) 0.0153(5) 0.0034(4) 0.0043(4) 0.0063(5) C19 0.0167(5) 0.0154(5) 0.0189(5) 0.0059(4) 0.0057(4) 0.0043(4) C20 0.0332(8) 0.0317(8) 0.0241(7) -0.0060(6) 0.0095(6) -0.0069(6) C1G 0.0485(10) 0.0306(8) 0.0405(8) 0.0063(6) 0.0118(7) 0.0092(7) C2G 0.0320(8) 0.0433(9) 0.0241(7) 0.0010(6) 0.0068(6) 0.0120(7) C3G 0.0470(9) 0.0450(9) 0.0303(7) 0.0175(7) 0.0125(7) 0.0148(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken "into account individually in the estimation of esds in distances, angles" and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4498(12) . ? O1 H1 0.950(7) . ? O2 C12 1.3871(13) . ? O2 C6 1.3894(13) . ? O3 C17 1.3726(13) . ? O3 C20 1.4241(15) . ? C1 C2 1.3988(15) . ? C1 C6 1.3892(16) . ? C2 H2 0.9500 . ? C3 C2 1.3856(16) . ? C3 C4 1.3922(17) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C4 1.3825(16) . ? C5 H5 0.9500 . ? C6 C5 1.3917(16) . ? C7 C12 1.3873(16) . ? C7 C8 1.4017(16) . ? C8 C9 1.3854(16) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C9 1.3934(18) . ? C10 H10 0.9500 . ? C11 C10 1.3797(17) . ? C11 C12 1.3931(15) . ? C11 H11 0.9500 . ? C13 C1 1.5211(15) . ? C13 C7 1.5241(14) . ? C14 C13 1.5255(15) . ? C14 C15 1.3945(15) . ? C14 C19 1.3893(15) . ? C15 H15 0.9500 . ? C16 C15 1.3875(16) . ? C16 C17 1.3870(16) . ? C16 H16 0.9500 . ? C17 C18 1.3926(16) . ? C18 H18 0.9500 . ? C19 C18 1.3928(16) . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C1G C3G 1.384(2) 2 ? C1G H1G 0.9500 . ? C2G C1G 1.375(2) . ? C2G C3G 1.377(2) . ? C2G H2G 0.9500 . ? C3G C1G 1.384(2) 2 ? C3G H3G 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C13 C1 108.41(8) . . ? O1 C13 C14 106.30(8) . . ? O1 C13 C7 108.46(8) . . ? O2 C12 C11 115.13(10) . . ? O2 C12 C7 122.57(10) . . ? O2 C6 C5 115.27(10) . . ? O3 C17 C16 115.77(10) . . ? O3 C17 C18 124.23(10) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? C1 C13 C14 112.48(9) . . ? C1 C13 C7 109.40(9) . . ? C1 C2 H2 119.3 . . ? C1 C6 C5 122.38(10) . . ? C1 C6 O2 122.33(10) . . ? C2 C1 C13 121.48(10) . . ? C2 C3 C4 119.90(10) . . ? C2 C3 H3 120.0 . . ? C3 C2 C1 121.36(11) . . ? C3 C2 H2 119.3 . . ? C3 C4 H4 120.0 . . ? C4 C3 H3 120.0 . . ? C4 C5 C6 119.07(11) . . ? C4 C5 H5 120.5 . . ? C5 C4 C3 120.05(10) . . ? C5 C4 H4 120.0 . . ? C6 C1 C13 121.00(9) . . ? C6 C1 C2 117.22(10) . . ? C6 C5 H5 120.5 . . ? C7 C12 C11 122.30(10) . . ? C7 C13 C14 111.62(9) . . ? C7 C8 H8 119.4 . . ? C8 C7 C13 121.75(10) . . ? C8 C9 C10 119.92(11) . . ? C8 C9 H9 120.0 . . ? C9 C10 H10 120.0 . . ? C9 C8 C7 121.24(11) . . ? C9 C8 H8 119.4 . . ? C10 C11 C12 119.18(11) . . ? C10 C11 H11 120.4 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.03(11) . . ? C11 C10 H10 120.0 . . ? C12 C11 H11 120.4 . . ? C12 C7 C13 120.77(10) . . ? C12 C7 C8 117.26(10) . . ? C12 O2 C6 118.19(9) . . ? C13 O1 H1 107.1(10) . . ? C14 C15 H15 119.8 . . ? C14 C19 C18 121.58(10) . . ? C14 C19 H19 119.2 . . ? C15 C14 C13 121.95(10) . . ? C15 C16 H16 119.8 . . ? C16 C15 C14 120.47(10) . . ? C16 C15 H15 119.8 . . ? C16 C17 C18 119.99(10) . . ? C17 C16 C15 120.38(11) . . ? C17 C16 H16 119.8 . . ? C17 C18 C19 119.02(10) . . ? C17 C18 H18 120.5 . . ? C17 O3 C20 117.27(9) . . ? C18 C19 H19 119.2 . . ? C19 C14 C13 119.51(10) . . ? C19 C14 C15 118.53(10) . . ? C19 C18 H18 120.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1G C2G C3G 119.70(14) . . ? C1G C2G H2G 120.2 . . ? C1G C3G H3G 119.9 2 . ? C2G C1G C3G 120.17(15) . 2 ? C2G C1G H1G 119.9 . . ? C2G C3G C1G 120.13(14) . 2 ? C2G C3G H3G 119.9 . . ? C3G C1G H1G 119.9 2 . ? C3G C2G H2G 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C13 C1 C2 78.23(12) . . . . ? O1 C13 C1 C6 -95.30(11) . . . . ? O1 C13 C7 C12 94.65(11) . . . . ? O1 C13 C7 C8 -79.75(12) . . . . ? O2 C6 C5 C4 178.65(10) . . . . ? O3 C17 C18 C19 -179.94(10) . . . . ? C1 C13 C7 C12 -23.42(14) . . . . ? C1 C13 C7 C8 162.18(10) . . . . ? C1 C6 C5 C4 -0.40(17) . . . . ? C2 C1 C6 C5 -0.95(16) . . . . ? C2 C1 C6 O2 -179.93(9) . . . . ? C2 C3 C4 C5 -0.97(17) . . . . ? C4 C3 C2 C1 -0.43(17) . . . . ? C6 C1 C2 C3 1.36(16) . . . . ? C6 C5 C4 C3 1.37(17) . . . . ? C6 O2 C12 C11 -168.46(9) . . . . ? C6 O2 C12 C7 12.08(15) . . . . ? C7 C13 C1 C2 -163.67(10) . . . . ? C7 C13 C1 C6 22.81(14) . . . . ? C7 C8 C9 C10 0.69(18) . . . . ? C8 C7 C12 C11 2.64(17) . . . . ? C8 C7 C12 O2 -177.93(10) . . . . ? C10 C11 C12 C7 -0.80(17) . . . . ? C10 C11 C12 O2 179.74(10) . . . . ? C11 C10 C9 C8 1.25(18) . . . . ? C12 C11 C10 C9 -1.20(18) . . . . ? C12 C7 C8 C9 -2.57(17) . . . . ? C12 O2 C6 C1 -12.74(15) . . . . ? C12 O2 C6 C5 168.21(9) . . . . ? C13 C1 C2 C3 -172.40(10) . . . . ? C13 C1 C6 C5 172.84(10) . . . . ? C13 C1 C6 O2 -6.14(16) . . . . ? C13 C14 C15 C16 177.37(10) . . . . ? C13 C14 C19 C18 -177.29(10) . . . . ? C13 C7 C12 C11 -172.01(10) . . . . ? C13 C7 C12 O2 7.42(16) . . . . ? C13 C7 C8 C9 172.02(10) . . . . ? C14 C13 C1 C2 -39.02(14) . . . . ? C14 C13 C1 C6 147.46(10) . . . . ? C14 C13 C7 C12 -148.56(10) . . . . ? C14 C13 C7 C8 37.03(14) . . . . ? C14 C19 C18 C17 -0.11(17) . . . . ? C15 C14 C13 C1 120.59(11) . . . . ? C15 C14 C13 C7 -115.99(11) . . . . ? C15 C14 C13 O1 2.09(13) . . . . ? C15 C14 C19 C18 1.28(17) . . . . ? C15 C16 C17 C18 1.30(17) . . . . ? C15 C16 C17 O3 -179.84(10) . . . . ? C16 C17 C18 C19 -1.19(17) . . . . ? C17 C16 C15 C14 -0.11(17) . . . . ? C19 C14 C13 C1 -60.89(13) . . . . ? C19 C14 C13 C7 62.53(13) . . . . ? C19 C14 C13 O1 -179.39(9) . . . . ? C19 C14 C15 C16 -1.17(16) . . . . ? C20 O3 C17 C16 176.85(11) . . . . ? C20 O3 C17 C18 -4.35(17) . . . . ? C1G C2G C3G C1G 0.5(3) . . . 2 ? C3G C2G C1G C3G -0.5(3) . . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.950(7) 1.916(7) 2.8652(11) 176.8(15) 2_566 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.297 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.058 _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol benzene clathrate' data_c:\opix\myexam~1\a1oxy\a1oxy _database_code_depnum_ccdc_archive 'CCDC 253841' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol o-xylene clathrate ; _chemical_formula_moiety 'C20 H16 O3.C4 H5' _chemical_formula_sum 'C24 H21 O3' _chemical_formula_weight 357.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.36540(10) _cell_length_b 9.06520(10) _cell_length_c 12.8730(3) _cell_angle_alpha 96.6960(10) _cell_angle_beta 94.0480(10) _cell_angle_gamma 109.7170(10) _cell_volume 906.38(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_min 0.9716 _exptl_absorpt_correction_T_max 0.9831 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1.0\%, 55s per \%, 2 iterations. ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 7595 _diffrn_reflns_av_R_equivalents 0.0108 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.44 _reflns_number_total 4095 _reflns_number_gt 3609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^2^+2.6123P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4095 _refine_ls_number_parameters 233 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0904 _refine_ls_wR_factor_ref 0.2341 _refine_ls_wR_factor_gt 0.2273 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2808(2) 0.2134(2) 0.46869(14) 0.0163(4) Uani 1 1 d D . . C1 C -0.0305(3) 0.2280(3) 0.38218(19) 0.0148(5) Uani 1 1 d . . . H1 H -0.209(5) 0.304(3) 0.518(3) 0.051(12) Uiso 1 1 d D . . O2 O 0.0796(2) 0.5136(2) 0.38408(15) 0.0189(4) Uani 1 1 d . . . C2 C 0.0105(3) 0.0930(3) 0.3935(2) 0.0188(5) Uani 1 1 d . . . H2 H -0.0782 -0.0078 0.3825 0.023 Uiso 1 1 calc R . . C3 C 0.1772(3) 0.1026(3) 0.4204(2) 0.0207(6) Uani 1 1 d . . . H3 H 0.2021 0.0094 0.4281 0.025 Uiso 1 1 calc R . . C4 C 0.3083(3) 0.2495(3) 0.4362(2) 0.0203(5) Uani 1 1 d . . . H4 H 0.4225 0.2567 0.4561 0.024 Uiso 1 1 calc R . . C5 C 0.2727(3) 0.3853(3) 0.4229(2) 0.0193(5) Uani 1 1 d . . . H5 H 0.3620 0.4856 0.4323 0.023 Uiso 1 1 calc R . . C6 C 0.1041(3) 0.3720(3) 0.39555(19) 0.0157(5) Uani 1 1 d . . . C7 C -0.2224(3) 0.3695(3) 0.32676(19) 0.0149(5) Uani 1 1 d . . . C8 C -0.3762(3) 0.3778(3) 0.2818(2) 0.0182(5) Uani 1 1 d . . . H8 H -0.4759 0.2852 0.2700 0.022 Uiso 1 1 calc R . . C9 C -0.3858(4) 0.5179(3) 0.2544(2) 0.0210(6) Uani 1 1 d . . . H9 H -0.4919 0.5215 0.2255 0.025 Uiso 1 1 calc R . . C10 C -0.2399(4) 0.6535(3) 0.2690(2) 0.0218(6) Uani 1 1 d . . . H10 H -0.2462 0.7496 0.2499 0.026 Uiso 1 1 calc R . . C11 C -0.0859(3) 0.6482(3) 0.3114(2) 0.0202(5) Uani 1 1 d . . . H11 H 0.0143 0.7401 0.3208 0.024 Uiso 1 1 calc R . . C12 C -0.0793(3) 0.5067(3) 0.3401(2) 0.0163(5) Uani 1 1 d . . . C13 C -0.2153(3) 0.2203(3) 0.36742(19) 0.0136(5) Uani 1 1 d . . . C14 C -0.3309(3) 0.0708(3) 0.29505(19) 0.0143(5) Uani 1 1 d . . . C15 C -0.4677(3) -0.0416(3) 0.3299(2) 0.0167(5) Uani 1 1 d . . . H15 H -0.4888 -0.0276 0.4013 0.020 Uiso 1 1 calc R . . C16 C -0.5734(3) -0.1737(3) 0.2612(2) 0.0193(5) Uani 1 1 d . . . H16 H -0.6659 -0.2499 0.2859 0.023 Uiso 1 1 calc R . . C17 C -0.5447(3) -0.1951(3) 0.1565(2) 0.0184(5) Uani 1 1 d . . . C18 C -0.4072(4) -0.0850(3) 0.1207(2) 0.0196(5) Uani 1 1 d . . . H18 H -0.3858 -0.0994 0.0494 0.023 Uiso 1 1 calc R . . C19 C -0.3016(3) 0.0463(3) 0.1905(2) 0.0180(5) Uani 1 1 d . . . H19 H -0.2072 0.1210 0.1663 0.022 Uiso 1 1 calc R . . O3 O -0.6566(3) -0.3290(2) 0.09508(16) 0.0265(5) Uani 1 1 d . . . C20 C -0.6335(5) -0.3511(4) -0.0137(2) 0.0330(7) Uani 1 1 d . . . H20A H -0.6378 -0.2590 -0.0452 0.049 Uiso 1 1 calc R . . H20B H -0.7245 -0.4467 -0.0501 0.049 Uiso 1 1 calc R . . H20C H -0.5222 -0.3627 -0.0204 0.049 Uiso 1 1 calc R . . C1G C 0.1632(11) 0.1851(10) 0.1329(7) 0.0447(17) Uiso 0.50 1 d P . . C2G C 0.0939(11) 0.2645(10) 0.0638(7) 0.0457(18) Uiso 0.50 1 d P . . C3G C 0.0063(9) 0.2045(8) -0.0183(6) 0.0871(18) Uiso 1 1 d . . . C4G C -0.0379(6) 0.0357(6) -0.0369(4) 0.0586(11) Uiso 1 1 d . . . C5G C -0.1568(9) -0.0586(8) -0.1279(6) 0.0873(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0162(9) 0.0163(9) 0.0146(9) 0.0012(7) 0.0025(7) 0.0036(7) C1 0.0142(11) 0.0165(12) 0.0138(11) 0.0017(9) 0.0014(9) 0.0058(9) O2 0.0150(9) 0.0129(8) 0.0270(10) 0.0015(7) -0.0023(7) 0.0040(7) C2 0.0181(12) 0.0158(12) 0.0222(13) 0.0026(9) 0.0007(10) 0.0059(10) C3 0.0201(13) 0.0208(13) 0.0248(13) 0.0045(10) 0.0022(10) 0.0115(10) C4 0.0149(12) 0.0256(14) 0.0216(13) 0.0022(10) 0.0004(10) 0.0096(10) C5 0.0146(12) 0.0192(12) 0.0221(13) 0.0006(10) 0.0007(10) 0.0042(10) C6 0.0175(12) 0.0149(11) 0.0151(11) 0.0011(9) 0.0010(9) 0.0066(9) C7 0.0157(12) 0.0156(11) 0.0140(11) 0.0017(9) 0.0020(9) 0.0064(9) C8 0.0173(12) 0.0178(12) 0.0189(12) 0.0008(9) -0.0002(9) 0.0066(10) C9 0.0209(13) 0.0215(13) 0.0220(13) 0.0023(10) -0.0029(10) 0.0104(11) C10 0.0269(14) 0.0162(12) 0.0243(13) 0.0044(10) 0.0000(11) 0.0100(11) C11 0.0206(13) 0.0139(12) 0.0243(13) 0.0022(10) 0.0014(10) 0.0042(10) C12 0.0161(12) 0.0170(12) 0.0167(11) 0.0018(9) 0.0012(9) 0.0073(10) C13 0.0137(11) 0.0147(11) 0.0130(11) 0.0019(9) 0.0015(8) 0.0056(9) C14 0.0140(11) 0.0130(11) 0.0166(12) 0.0018(9) -0.0002(9) 0.0061(9) C15 0.0158(12) 0.0162(11) 0.0182(12) 0.0025(9) 0.0024(9) 0.0056(9) C16 0.0159(12) 0.0169(12) 0.0234(13) 0.0041(10) 0.0014(10) 0.0033(10) C17 0.0187(12) 0.0134(11) 0.0202(13) -0.0007(9) -0.0047(10) 0.0044(10) C18 0.0256(13) 0.0180(12) 0.0152(12) 0.0025(9) 0.0011(10) 0.0081(10) C19 0.0193(12) 0.0152(12) 0.0187(12) 0.0041(9) 0.0020(10) 0.0045(10) O3 0.0300(11) 0.0187(10) 0.0210(10) -0.0023(8) -0.0043(8) -0.0009(8) C20 0.0423(18) 0.0266(15) 0.0199(14) -0.0025(11) -0.0039(12) 0.0025(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.449(3) . ? O1 H1 0.965(7) . ? C1 C6 1.389(3) . ? C1 C2 1.398(3) . ? C1 C13 1.521(3) . ? O2 C12 1.386(3) . ? O2 C6 1.389(3) . ? C2 C3 1.384(4) . ? C2 H2 0.9500 . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.387(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C7 C12 1.388(4) . ? C7 C8 1.402(3) . ? C7 C13 1.524(3) . ? C8 C9 1.384(4) . ? C8 H8 0.9500 . ? C9 C10 1.392(4) . ? C9 H9 0.9500 . ? C10 C11 1.381(4) . ? C10 H10 0.9500 . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C13 C14 1.528(3) . ? C14 C19 1.390(4) . ? C14 C15 1.393(3) . ? C15 C16 1.389(4) . ? C15 H15 0.9500 . ? C16 C17 1.388(4) . ? C16 H16 0.9500 . ? C17 O3 1.371(3) . ? C17 C18 1.393(4) . ? C18 C19 1.391(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O3 C20 1.427(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C1G C5G 1.124(10) 2 ? C1G C2G 1.415(11) . ? C2G C3G 1.199(10) . ? C3G C4G 1.434(8) . ? C4G C4G 1.434(10) 2 ? C4G C5G 1.456(8) . ? C5G C1G 1.124(10) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 H1 110(3) . . ? C6 C1 C2 117.2(2) . . ? C6 C1 C13 121.1(2) . . ? C2 C1 C13 121.4(2) . . ? C12 O2 C6 118.15(19) . . ? C3 C2 C1 121.6(2) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 118.8(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? O2 C6 C1 122.4(2) . . ? O2 C6 C5 115.1(2) . . ? C1 C6 C5 122.5(2) . . ? C12 C7 C8 117.2(2) . . ? C12 C7 C13 121.2(2) . . ? C8 C7 C13 121.5(2) . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.3(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? O2 C12 C7 122.6(2) . . ? O2 C12 C11 115.2(2) . . ? C7 C12 C11 122.2(2) . . ? O1 C13 C1 108.59(19) . . ? O1 C13 C7 108.74(19) . . ? C1 C13 C7 109.4(2) . . ? O1 C13 C14 106.23(19) . . ? C1 C13 C14 112.39(19) . . ? C7 C13 C14 111.39(19) . . ? C19 C14 C15 118.5(2) . . ? C19 C14 C13 119.4(2) . . ? C15 C14 C13 122.0(2) . . ? C16 C15 C14 120.5(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? O3 C17 C16 115.8(2) . . ? O3 C17 C18 124.3(2) . . ? C16 C17 C18 119.9(2) . . ? C19 C18 C17 119.2(2) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C14 C19 C18 121.5(2) . . ? C14 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C17 O3 C20 117.0(2) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5G C1G C2G 132.2(9) 2 . ? C3G C2G C1G 125.6(8) . . ? C2G C3G C4G 112.8(7) . . ? C3G C4G C4G 117.9(6) . 2 ? C3G C4G C5G 120.4(5) . . ? C4G C4G C5G 121.7(6) 2 . ? C1G C5G C4G 109.1(7) 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.1(4) . . . . ? C13 C1 C2 C3 -171.5(2) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 -1.3(4) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C12 O2 C6 C1 -11.5(4) . . . . ? C12 O2 C6 C5 169.4(2) . . . . ? C2 C1 C6 O2 178.6(2) . . . . ? C13 C1 C6 O2 -7.7(4) . . . . ? C2 C1 C6 C5 -2.3(4) . . . . ? C13 C1 C6 C5 171.3(2) . . . . ? C4 C5 C6 O2 179.8(2) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C12 C7 C8 C9 -1.5(4) . . . . ? C13 C7 C8 C9 173.6(2) . . . . ? C7 C8 C9 C10 1.5(4) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C6 O2 C12 C7 13.1(4) . . . . ? C6 O2 C12 C11 -167.7(2) . . . . ? C8 C7 C12 O2 179.7(2) . . . . ? C13 C7 C12 O2 4.5(4) . . . . ? C8 C7 C12 C11 0.5(4) . . . . ? C13 C7 C12 C11 -174.7(2) . . . . ? C10 C11 C12 O2 -178.6(2) . . . . ? C10 C11 C12 C7 0.6(4) . . . . ? C6 C1 C13 O1 -96.0(3) . . . . ? C2 C1 C13 O1 77.4(3) . . . . ? C6 C1 C13 C7 22.5(3) . . . . ? C2 C1 C13 C7 -164.1(2) . . . . ? C6 C1 C13 C14 146.8(2) . . . . ? C2 C1 C13 C14 -39.8(3) . . . . ? C12 C7 C13 O1 97.5(3) . . . . ? C8 C7 C13 O1 -77.5(3) . . . . ? C12 C7 C13 C1 -21.0(3) . . . . ? C8 C7 C13 C1 164.0(2) . . . . ? C12 C7 C13 C14 -145.8(2) . . . . ? C8 C7 C13 C14 39.2(3) . . . . ? O1 C13 C14 C19 178.4(2) . . . . ? C1 C13 C14 C19 -63.0(3) . . . . ? C7 C13 C14 C19 60.1(3) . . . . ? O1 C13 C14 C15 -0.5(3) . . . . ? C1 C13 C14 C15 118.1(2) . . . . ? C7 C13 C14 C15 -118.7(2) . . . . ? C19 C14 C15 C16 -0.9(4) . . . . ? C13 C14 C15 C16 178.0(2) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C15 C16 C17 O3 -179.8(2) . . . . ? C15 C16 C17 C18 1.2(4) . . . . ? O3 C17 C18 C19 -179.7(2) . . . . ? C16 C17 C18 C19 -0.8(4) . . . . ? C15 C14 C19 C18 1.3(4) . . . . ? C13 C14 C19 C18 -177.6(2) . . . . ? C17 C18 C19 C14 -0.5(4) . . . . ? C16 C17 O3 C20 177.9(3) . . . . ? C18 C17 O3 C20 -3.1(4) . . . . ? C5G C1G C2G C3G 1.6(17) 2 . . . ? C1G C2G C3G C4G 5.7(12) . . . . ? C2G C3G C4G C4G -5.5(10) . . . 2 ? C2G C3G C4G C5G 174.2(7) . . . . ? C3G C4G C5G C1G 174.0(7) . . . 2 ? C4G C4G C5G C1G -6.3(11) 2 . . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.965(7) 1.898(7) 2.863(2) 177(4) 2_566 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.741 _refine_diff_density_min -1.089 _refine_diff_density_rms 0.102 _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol o-xylene clathrate' data_c:\opix\myexam~1\a1mxyrt\a1mxyrt _database_code_depnum_ccdc_archive 'CCDC 253842' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol m-xylene clathrate ; _chemical_formula_moiety 'C20 H16 O3.C4 H5' _chemical_formula_sum 'C24 H21 O3' _chemical_formula_weight 357.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.49020(10) _cell_length_b 9.19230(10) _cell_length_c 12.9946(2) _cell_angle_alpha 95.6200(10) _cell_angle_beta 94.8400(10) _cell_angle_gamma 109.6600(10) _cell_volume 942.97(2) _cell_formula_units_Z 2 _cell_measurement_temperature 283 _cell_measurement_reflns_used 'All data' _exptl_crystal_description colourless _exptl_crystal_colour cuboid _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9758 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1.0\%, 55s per \%, 2 iterations. ; _diffrn_ambient_temperature 283 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 7718 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.06 _reflns_number_total 4106 _reflns_number_gt 3208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1415P)^2^+0.3756P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4106 _refine_ls_number_parameters 237 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.2463 _refine_ls_wR_factor_gt 0.2286 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.27697(18) 0.21665(17) 0.46846(11) 0.0424(4) Uani 1 1 d D . . C1 C -0.2188(2) 0.3744(2) 0.32842(15) 0.0380(5) Uani 1 1 d . . . O2 O 0.07889(19) 0.51333(17) 0.38479(13) 0.0495(4) Uani 1 1 d . . . C2 C -0.3703(3) 0.3846(3) 0.28441(18) 0.0466(5) Uani 1 1 d . . . H2 H -0.4694 0.2945 0.2738 0.056 Uiso 1 1 calc R . . O3 O -0.6376(3) -0.3130(2) 0.09874(16) 0.0785(7) Uani 1 1 d . . . C3 C -0.3785(3) 0.5230(3) 0.2561(2) 0.0565(6) Uani 1 1 d . . . H3 H -0.4829 0.5279 0.2272 0.068 Uiso 1 1 calc R . . C4 C -0.2338(3) 0.6551(3) 0.2699(2) 0.0581(6) Uani 1 1 d . . . H4 H -0.2394 0.7503 0.2503 0.070 Uiso 1 1 calc R . . C5 C -0.0833(3) 0.6485(3) 0.3118(2) 0.0547(6) Uani 1 1 d . . . H5 H 0.0161 0.7383 0.3207 0.066 Uiso 1 1 calc R . . C6 C -0.0775(3) 0.5081(2) 0.34122(16) 0.0418(5) Uani 1 1 d . . . C7 C -0.0309(2) 0.2322(2) 0.38359(15) 0.0380(5) Uani 1 1 d . . . C8 C 0.0093(3) 0.0990(3) 0.39421(19) 0.0482(5) Uani 1 1 d . . . H8 H -0.0783 0.0000 0.3834 0.058 Uiso 1 1 calc R . . C9 C 0.1744(3) 0.1076(3) 0.4202(2) 0.0549(6) Uani 1 1 d . . . H9 H 0.1989 0.0154 0.4277 0.066 Uiso 1 1 calc R . . C10 C 0.3034(3) 0.2509(3) 0.4352(2) 0.0538(6) Uani 1 1 d . . . H10 H 0.4162 0.2574 0.4545 0.065 Uiso 1 1 calc R . . C11 C 0.2684(3) 0.3844(3) 0.42223(19) 0.0500(5) Uani 1 1 d . . . H11 H 0.3568 0.4827 0.4310 0.060 Uiso 1 1 calc R . . C12 C 0.1025(3) 0.3735(2) 0.39622(16) 0.0397(5) Uani 1 1 d . . . C13 C -0.2126(2) 0.2261(2) 0.36851(15) 0.0364(4) Uani 1 1 d . . . C14 C -0.3264(2) 0.0806(2) 0.29690(15) 0.0385(5) Uani 1 1 d . . . C15 C -0.4607(3) -0.0313(3) 0.32980(18) 0.0456(5) Uani 1 1 d . . . H15 H -0.4836 -0.0189 0.3998 0.055 Uiso 1 1 calc R . . C16 C -0.5620(3) -0.1610(3) 0.2616(2) 0.0543(6) Uani 1 1 d . . . H16 H -0.6533 -0.2371 0.2853 0.065 Uiso 1 1 calc R . . C17 C -0.5311(3) -0.1800(3) 0.15973(19) 0.0530(6) Uani 1 1 d . . . C18 C -0.3978(4) -0.0701(3) 0.12556(18) 0.0561(6) Uani 1 1 d . . . H18 H -0.3758 -0.0825 0.0554 0.067 Uiso 1 1 calc R . . C19 C -0.2964(3) 0.0584(3) 0.19440(17) 0.0492(5) Uani 1 1 d . . . H19 H -0.2039 0.1333 0.1708 0.059 Uiso 1 1 calc R . . C20 C -0.6102(7) -0.3367(5) -0.0066(3) 0.1067(14) Uani 1 1 d . . . H20A H -0.4964 -0.3398 -0.0094 0.160 Uiso 1 1 calc R . . H20B H -0.6221 -0.2511 -0.0422 0.160 Uiso 1 1 calc R . . H20C H -0.6932 -0.4357 -0.0410 0.160 Uiso 1 1 calc R . . C1G C 0.1220(13) -0.0188(12) 0.1196(8) 0.113(3) Uiso 0.50 1 d P . . C2G C 0.0341(10) -0.1047(9) 0.0340(6) 0.152(2) Uiso 1 1 d . . . C3G C -0.0748(14) -0.0665(14) -0.0478(9) 0.116(3) Uiso 0.50 1 d P . . C4G C -0.1559(13) -0.1525(12) -0.1257(9) 0.208(3) Uiso 1 1 d . . . C5G C -0.0491(11) -0.1629(10) -0.0396(7) 0.0883(19) Uiso 0.50 1 d P . . C6G C -0.084(3) -0.332(3) -0.074(2) 0.270(11) Uiso 0.50 1 d P . . H1 H -0.210(4) 0.301(2) 0.5223(19) 0.083(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0401(8) 0.0449(8) 0.0403(8) 0.0028(6) 0.0060(6) 0.0129(6) C1 0.0377(10) 0.0388(10) 0.0401(10) 0.0029(8) 0.0038(8) 0.0174(8) O2 0.0375(8) 0.0375(8) 0.0702(10) 0.0038(7) -0.0044(7) 0.0122(6) C2 0.0408(11) 0.0461(11) 0.0542(12) 0.0057(9) -0.0010(9) 0.0187(9) O3 0.0892(15) 0.0564(11) 0.0699(13) -0.0163(9) -0.0213(11) 0.0134(10) C3 0.0542(14) 0.0553(14) 0.0651(15) 0.0055(11) -0.0076(11) 0.0301(11) C4 0.0637(15) 0.0445(12) 0.0712(16) 0.0115(11) -0.0023(12) 0.0269(11) C5 0.0561(14) 0.0387(11) 0.0689(15) 0.0085(10) 0.0010(11) 0.0173(10) C6 0.0403(11) 0.0399(10) 0.0465(11) 0.0030(8) 0.0016(8) 0.0172(9) C7 0.0339(10) 0.0407(10) 0.0402(10) 0.0045(8) 0.0021(8) 0.0151(8) C8 0.0424(11) 0.0443(12) 0.0611(13) 0.0094(10) 0.0033(10) 0.0193(9) C9 0.0487(13) 0.0569(14) 0.0678(15) 0.0109(11) 0.0033(11) 0.0301(11) C10 0.0381(11) 0.0664(15) 0.0625(14) 0.0082(11) 0.0023(10) 0.0266(11) C11 0.0351(11) 0.0514(12) 0.0604(13) 0.0024(10) 0.0007(9) 0.0137(9) C12 0.0364(10) 0.0400(10) 0.0436(10) 0.0031(8) 0.0026(8) 0.0155(8) C13 0.0332(9) 0.0386(10) 0.0388(10) 0.0044(8) 0.0034(7) 0.0149(8) C14 0.0371(10) 0.0394(10) 0.0410(10) 0.0036(8) 0.0001(8) 0.0175(8) C15 0.0387(11) 0.0461(11) 0.0489(12) 0.0007(9) 0.0043(9) 0.0123(9) C16 0.0431(12) 0.0471(12) 0.0659(15) 0.0002(10) 0.0006(10) 0.0103(10) C17 0.0565(14) 0.0433(12) 0.0551(13) -0.0049(10) -0.0140(10) 0.0200(10) C18 0.0758(17) 0.0539(13) 0.0414(12) 0.0008(10) 0.0001(11) 0.0294(12) C19 0.0549(13) 0.0474(12) 0.0450(12) 0.0057(9) 0.0066(10) 0.0174(10) C20 0.156(4) 0.079(2) 0.0616(19) -0.0213(16) -0.021(2) 0.027(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.450(2) . ? O1 H1 0.969(8) . ? C1 C6 1.383(3) . ? C1 C2 1.399(3) . ? C1 C13 1.521(3) . ? O2 C6 1.382(3) . ? O2 C12 1.386(2) . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? O3 C17 1.373(3) . ? O3 C20 1.416(4) . ? C3 C4 1.390(4) . ? C3 H3 0.9500 . ? C4 C5 1.370(4) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 H5 0.9500 . ? C7 C12 1.390(3) . ? C7 C8 1.393(3) . ? C7 C13 1.520(3) . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 C10 1.384(4) . ? C9 H9 0.9500 . ? C10 C11 1.378(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C13 C14 1.524(3) . ? C14 C19 1.386(3) . ? C14 C15 1.386(3) . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C16 C17 1.378(4) . ? C16 H16 0.9500 . ? C17 C18 1.379(4) . ? C18 C19 1.385(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C1G C2G 1.308(11) . ? C1G C3G 1.391(14) 2 ? C1G C4G 1.495(13) 2 ? C2G C5G 1.109(9) . ? C2G C3G 1.482(12) 2 ? C2G C3G 1.495(13) . ? C3G C5G 0.995(11) . ? C3G C4G 1.218(12) . ? C3G C1G 1.391(14) 2 ? C3G C2G 1.482(12) 2 ? C3G C3G 1.74(2) 2 ? C4G C5G 1.411(13) . ? C4G C1G 1.495(13) 2 ? C5G C6G 1.49(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 H1 113.9(19) . . ? C6 C1 C2 117.22(19) . . ? C6 C1 C13 121.26(17) . . ? C2 C1 C13 121.34(18) . . ? C6 O2 C12 118.16(16) . . ? C3 C2 C1 121.3(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C17 O3 C20 117.6(3) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? O2 C6 C1 122.71(18) . . ? O2 C6 C5 115.13(19) . . ? C1 C6 C5 122.2(2) . . ? C12 C7 C8 116.99(18) . . ? C12 C7 C13 121.09(17) . . ? C8 C7 C13 121.71(18) . . ? C9 C8 C7 121.5(2) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.3(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? O2 C12 C11 115.37(18) . . ? O2 C12 C7 122.33(17) . . ? C11 C12 C7 122.30(19) . . ? O1 C13 C7 108.61(15) . . ? O1 C13 C1 108.86(15) . . ? C7 C13 C1 109.39(16) . . ? O1 C13 C14 106.11(15) . . ? C7 C13 C14 112.00(15) . . ? C1 C13 C14 111.73(16) . . ? C19 C14 C15 118.1(2) . . ? C19 C14 C13 119.27(19) . . ? C15 C14 C13 122.65(18) . . ? C14 C15 C16 120.7(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.3(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? O3 C17 C16 115.9(2) . . ? O3 C17 C18 124.3(2) . . ? C16 C17 C18 119.8(2) . . ? C17 C18 C19 119.4(2) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C14 121.6(2) . . ? C18 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C2G C1G C3G 66.5(7) . 2 ? C2G C1G C4G 116.3(9) . 2 ? C3G C1G C4G 49.7(6) 2 2 ? C5G C2G C1G 171.0(10) . . ? C5G C2G C3G 112.4(9) . 2 ? C1G C2G C3G 59.4(7) . 2 ? C5G C2G C3G 41.7(6) . . ? C1G C2G C3G 129.4(9) . . ? C3G C2G C3G 71.8(8) 2 . ? C5G C3G C4G 78.6(11) . . ? C5G C3G C1G 144.6(12) . 2 ? C4G C3G C1G 69.5(8) . 2 ? C5G C3G C2G 153.5(12) . 2 ? C4G C3G C2G 123.6(11) . 2 ? C1G C3G C2G 54.0(6) 2 2 ? C5G C3G C2G 47.9(7) . . ? C4G C3G C2G 126.5(12) . . ? C1G C3G C2G 158.4(10) 2 . ? C2G C3G C2G 108.2(8) 2 . ? C5G C3G C3G 100.7(12) . 2 ? C4G C3G C3G 168.2(13) . 2 ? C1G C3G C3G 107.3(11) 2 2 ? C2G C3G C3G 54.4(7) 2 2 ? C2G C3G C3G 53.8(6) . 2 ? C3G C4G C5G 43.7(6) . . ? C3G C4G C1G 60.7(8) . 2 ? C5G C4G C1G 103.1(8) . 2 ? C3G C5G C2G 90.4(10) . . ? C3G C5G C4G 57.7(8) . . ? C2G C5G C4G 148.1(10) . . ? C3G C5G C6G 149.3(15) . . ? C2G C5G C6G 120.0(13) . . ? C4G C5G C6G 91.9(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.7(3) . . . . ? C13 C1 C2 C3 174.5(2) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C12 O2 C6 C1 13.5(3) . . . . ? C12 O2 C6 C5 -167.09(19) . . . . ? C2 C1 C6 O2 179.27(19) . . . . ? C13 C1 C6 O2 4.1(3) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C13 C1 C6 C5 -175.3(2) . . . . ? C4 C5 C6 O2 -178.6(2) . . . . ? C4 C5 C6 C1 0.8(4) . . . . ? C12 C7 C8 C9 2.4(3) . . . . ? C13 C7 C8 C9 -172.3(2) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C11 -1.4(4) . . . . ? C9 C10 C11 C12 1.4(4) . . . . ? C6 O2 C12 C11 168.70(19) . . . . ? C6 O2 C12 C7 -12.0(3) . . . . ? C10 C11 C12 O2 179.9(2) . . . . ? C10 C11 C12 C7 0.6(3) . . . . ? C8 C7 C12 O2 178.24(19) . . . . ? C13 C7 C12 O2 -7.0(3) . . . . ? C8 C7 C12 C11 -2.5(3) . . . . ? C13 C7 C12 C11 172.27(19) . . . . ? C12 C7 C13 O1 -96.8(2) . . . . ? C8 C7 C13 O1 77.6(2) . . . . ? C12 C7 C13 C1 21.9(3) . . . . ? C8 C7 C13 C1 -163.67(19) . . . . ? C12 C7 C13 C14 146.30(19) . . . . ? C8 C7 C13 C14 -39.2(3) . . . . ? C6 C1 C13 O1 98.1(2) . . . . ? C2 C1 C13 O1 -76.9(2) . . . . ? C6 C1 C13 C7 -20.5(3) . . . . ? C2 C1 C13 C7 164.52(18) . . . . ? C6 C1 C13 C14 -145.07(19) . . . . ? C2 C1 C13 C14 39.9(2) . . . . ? O1 C13 C14 C19 179.22(17) . . . . ? C7 C13 C14 C19 -62.4(2) . . . . ? C1 C13 C14 C19 60.7(2) . . . . ? O1 C13 C14 C15 -0.4(2) . . . . ? C7 C13 C14 C15 118.0(2) . . . . ? C1 C13 C14 C15 -118.9(2) . . . . ? C19 C14 C15 C16 -0.3(3) . . . . ? C13 C14 C15 C16 179.31(19) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C20 O3 C17 C16 179.8(3) . . . . ? C20 O3 C17 C18 -1.3(4) . . . . ? C15 C16 C17 O3 179.4(2) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? O3 C17 C18 C19 -178.8(2) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C17 C18 C19 C14 -0.7(4) . . . . ? C15 C14 C19 C18 0.9(3) . . . . ? C13 C14 C19 C18 -178.8(2) . . . . ? C3G C1G C2G C5G -27(6) 2 . . . ? C4G C1G C2G C5G -27(7) 2 . . . ? C4G C1G C2G C3G 0.1(8) 2 . . 2 ? C3G C1G C2G C3G -17.3(13) 2 . . . ? C4G C1G C2G C3G -17.3(15) 2 . . . ? C1G C2G C3G C5G -177.7(13) . . . . ? C3G C2G C3G C5G 166.6(13) 2 . . . ? C5G C2G C3G C4G -1.2(11) . . . . ? C1G C2G C3G C4G -179.0(11) . . . . ? C3G C2G C3G C4G 165.4(16) 2 . . . ? C5G C2G C3G C1G -134(3) . . . 2 ? C1G C2G C3G C1G 48(3) . . . 2 ? C3G C2G C3G C1G 32(2) 2 . . 2 ? C5G C2G C3G C2G -166.6(13) . . . 2 ? C1G C2G C3G C2G 15.7(12) . . . 2 ? C3G C2G C3G C2G 0.0 2 . . 2 ? C5G C2G C3G C3G -166.6(13) . . . 2 ? C1G C2G C3G C3G 15.7(12) . . . 2 ? C1G C3G C4G C5G 164.3(11) 2 . . . ? C2G C3G C4G C5G 164.2(15) 2 . . . ? C2G C3G C4G C5G 0.9(8) . . . . ? C3G C3G C4G C5G 88(7) 2 . . . ? C5G C3G C4G C1G -164.3(11) . . . 2 ? C2G C3G C4G C1G -0.1(9) 2 . . 2 ? C2G C3G C4G C1G -163.3(13) . . . 2 ? C3G C3G C4G C1G -76(7) 2 . . 2 ? C4G C3G C5G C2G 179.0(9) . . . . ? C1G C3G C5G C2G 153.0(19) 2 . . . ? C2G C3G C5G C2G 30(3) 2 . . . ? C3G C3G C5G C2G 11.0(11) 2 . . . ? C1G C3G C5G C4G -26.0(18) 2 . . . ? C2G C3G C5G C4G -149(3) 2 . . . ? C2G C3G C5G C4G -179.0(9) . . . . ? C3G C3G C5G C4G -168.0(13) 2 . . . ? C4G C3G C5G C6G -10(3) . . . . ? C1G C3G C5G C6G -36(4) 2 . . . ? C2G C3G C5G C6G -159(3) 2 . . . ? C2G C3G C5G C6G 171(3) . . . . ? C3G C3G C5G C6G -178(2) 2 . . . ? C1G C2G C5G C3G 11(6) . . . . ? C3G C2G C5G C3G -13.8(14) 2 . . . ? C1G C2G C5G C4G 13(7) . . . . ? C3G C2G C5G C4G -12(2) 2 . . . ? C3G C2G C5G C4G 1.6(15) . . . . ? C1G C2G C5G C6G -164(6) . . . . ? C3G C2G C5G C6G 171.3(14) 2 . . . ? C3G C2G C5G C6G -175.0(18) . . . . ? C1G C4G C5G C3G 14.0(10) 2 . . . ? C3G C4G C5G C2G -1.9(17) . . . . ? C1G C4G C5G C2G 12(2) 2 . . . ? C3G C4G C5G C6G 175.1(15) . . . . ? C1G C4G C5G C6G -170.8(12) 2 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.969(8) 1.927(8) 2.889(2) 172(3) 2_566 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.669 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.058 _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol m-xylene clathrate' data_c:\xprep\a1mxynew _database_code_depnum_ccdc_archive 'CCDC 253843' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol m-xylene clathrate ; _chemical_formula_moiety 'C20 H16 O3.C4 H5' _chemical_formula_sum 'C48 H42 O6' _chemical_formula_weight 714.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4150(2) _cell_length_b 18.2852(3) _cell_length_c 12.7741(4) _cell_angle_alpha 95.6370(10) _cell_angle_beta 94.9190(10) _cell_angle_gamma 109.7170(10) _cell_volume 1826.47(8) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 'all data' _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9718 _exptl_absorpt_correction_T_max 0.9833 _exptl_special_details ; "Complete sphere of data collected using COLLECT strategy (Nonius, 2000)." Crystal to detector distance = 40mm; combination of \f and \w scans of "1.0\%, 55s per \%, 2 iterations." ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 14802 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.12 _reflns_number_total 7957 _reflns_number_gt 4988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and "goodness of fit S are based on F^2^, conventional R-factors R are based" "on F, with F set to zero for negative F^2^. The threshold expression of" F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based "on F^2^ are statistically about twice as large as those based on F, and R-" factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.0460P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7957 _refine_ls_number_parameters 499 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 1.22353(12) 0.35759(6) 0.46397(8) 0.0175(2) Uani 1 1 d D . . O1B O 0.78228(12) 0.14259(6) 0.52421(8) 0.0182(2) Uani 1 1 d D . . O2A O 1.58224(12) 0.50944(6) 0.38585(8) 0.0193(3) Uani 1 1 d . . . O2B O 0.42677(12) -0.00426(6) 0.61688(8) 0.0213(3) Uani 1 1 d . . . O3A O 0.87395(14) 0.09327(6) 0.08185(9) 0.0293(3) Uani 1 1 d . . . O3B O 1.17092(13) 0.41509(6) 0.88932(8) 0.0258(3) Uani 1 1 d . . . C1A C 1.47422(18) 0.36747(9) 0.37863(11) 0.0156(3) Uani 1 1 d . . . H1A H 1.291(2) 0.4030(7) 0.5126(11) 0.037(5) Uiso 1 1 d D . . H1B H 0.712(2) 0.0953(7) 0.4787(13) 0.054(6) Uiso 1 1 d D . . C1B C 0.53847(18) 0.13709(9) 0.61352(11) 0.0168(3) Uani 1 1 d . . . C2A C 1.51595(19) 0.30056(9) 0.38639(12) 0.0198(4) Uani 1 1 d . . . C2B C 0.49819(19) 0.20382(9) 0.60038(12) 0.0201(4) Uani 1 1 d . . . H2A H 1.4280 0.2506 0.3738 0.024 Uiso 1 1 calc R . . H2B H 0.5869 0.2535 0.6098 0.024 Uiso 1 1 calc R . . C3A C 1.68269(19) 0.30504(9) 0.41208(12) 0.0224(4) Uani 1 1 d . . . C3B C 0.33195(19) 0.19946(9) 0.57385(12) 0.0221(4) Uani 1 1 d . . . H3A H 1.7082 0.2586 0.4172 0.027 Uiso 1 1 calc R . . H3B H 0.3076 0.2458 0.5652 0.027 Uiso 1 1 calc R . . C4A C 1.81227(19) 0.37772(9) 0.43034(12) 0.0215(4) Uani 1 1 d . . . C4B C 0.20069(19) 0.12721(9) 0.55983(12) 0.0221(4) Uani 1 1 d . . . H4A H 1.9263 0.3811 0.4498 0.026 Uiso 1 1 calc R . . H4B H 0.0869 0.1238 0.5393 0.027 Uiso 1 1 calc R . . C5A C 1.77601(19) 0.44481(9) 0.42038(12) 0.0200(4) Uani 1 1 d . . . C5B C 0.23611(19) 0.06045(9) 0.57587(12) 0.0208(4) Uani 1 1 d . . . H5A H 1.8647 0.4945 0.4309 0.024 Uiso 1 1 calc R . . H5B H 0.1467 0.0111 0.5686 0.025 Uiso 1 1 calc R . . C6A C 1.60808(18) 0.43899(9) 0.39469(11) 0.0163(3) Uani 1 1 d . . . C6B C 0.40291(19) 0.06600(9) 0.60263(12) 0.0178(3) Uani 1 1 d . . . C7A C 1.28262(18) 0.43842(8) 0.32317(11) 0.0162(3) Uani 1 1 d . . . C7B C 0.72990(18) 0.06582(9) 0.66921(11) 0.0167(3) Uani 1 1 d . . . C8A C 1.13098(19) 0.44314(9) 0.27586(12) 0.0199(3) Uani 1 1 d . . . C8B C 0.88359(19) 0.06011(9) 0.71089(12) 0.0201(4) Uani 1 1 d . . . H8A H 1.0320 0.3973 0.2624 0.024 Uiso 1 1 calc R . . H8B H 0.9839 0.1053 0.7202 0.024 Uiso 1 1 calc R . . C9A C 1.1216(2) 0.51281(9) 0.24822(12) 0.0226(4) Uani 1 1 d . . . C9B C 0.8938(2) -0.00964(9) 0.73903(12) 0.0234(4) Uani 1 1 d . . . H9A H 1.0165 0.5148 0.2176 0.027 Uiso 1 1 calc R . . H9B H 1.0002 -0.0122 0.7661 0.028 Uiso 1 1 calc R . . C10A C 1.2663(2) 0.58005(9) 0.26527(12) 0.0229(4) Uani 1 1 d . . . C10B C 0.7472(2) -0.07579(9) 0.72739(12) 0.0233(4) Uani 1 1 d . . . H10A H 1.2603 0.6279 0.2457 0.027 Uiso 1 1 calc R . . H10B H 0.7533 -0.1238 0.7464 0.028 Uiso 1 1 calc R . . C11A C 1.41856(19) 0.57720(9) 0.31055(12) 0.0212(4) Uani 1 1 d . . . C11B C 0.5932(2) -0.07178(9) 0.68829(12) 0.0230(4) Uani 1 1 d . . . H11A H 1.5180 0.6229 0.3219 0.025 Uiso 1 1 calc R . . H11B H 0.4925 -0.1166 0.6816 0.028 Uiso 1 1 calc R . . C12A C 1.42477(18) 0.50675(9) 0.33934(11) 0.0170(3) Uani 1 1 d . . . C12B C 0.58604(18) -0.00171(9) 0.65867(12) 0.0184(3) Uani 1 1 d . . . C13A C 1.29033(18) 0.36371(8) 0.36308(11) 0.0154(3) Uani 1 1 d . . . C13B C 0.72208(18) 0.14005(9) 0.62725(11) 0.0163(3) Uani 1 1 d . . . C14A C 1.17788(18) 0.29110(8) 0.28805(11) 0.0156(3) Uani 1 1 d . . . C14B C 0.84062(18) 0.21419(9) 0.69771(12) 0.0167(3) Uani 1 1 d . . . C15A C 1.03690(18) 0.23527(9) 0.31827(12) 0.0186(3) Uani 1 1 d . . . C15B C 0.96986(18) 0.27058(9) 0.65862(12) 0.0186(3) Uani 1 1 d . . . H15A H 1.0089 0.2417 0.3882 0.022 Uiso 1 1 calc R . . H15B H 0.9853 0.2635 0.5860 0.022 Uiso 1 1 calc R . . C16A C 0.93715(19) 0.17049(9) 0.24736(12) 0.0218(4) Uani 1 1 d . . . C16B C 1.07648(19) 0.33707(9) 0.72459(12) 0.0204(4) Uani 1 1 d . . . H16A H 0.8410 0.1329 0.2688 0.026 Uiso 1 1 calc R . . H16B H 1.1635 0.3754 0.6966 0.024 Uiso 1 1 calc R . . C17A C 0.97726(19) 0.16033(9) 0.14508(12) 0.0202(4) Uani 1 1 d . . . C17B C 1.05685(19) 0.34792(9) 0.83107(12) 0.0190(4) Uani 1 1 d . . . C18A C 1.11760(19) 0.21551(9) 0.11331(12) 0.0208(4) Uani 1 1 d . . . C18B C 0.92674(19) 0.29270(9) 0.87098(12) 0.0209(4) Uani 1 1 d . . . H18A H 1.1458 0.2090 0.0434 0.025 Uiso 1 1 calc R . . H18B H 0.9108 0.2999 0.9435 0.025 Uiso 1 1 calc R . . C19A C 1.21558(19) 0.28014(9) 0.18545(12) 0.0190(3) Uani 1 1 d . . . C19B C 0.82000(19) 0.22675(9) 0.80348(12) 0.0206(4) Uani 1 1 d . . . H19A H 1.3113 0.3180 0.1639 0.023 Uiso 1 1 calc R . . H19B H 0.7305 0.1893 0.8308 0.025 Uiso 1 1 calc R . . C20A C 0.9137(2) 0.08069(10) -0.02298(13) 0.0333(4) Uani 1 1 d . . . C20B C 1.1534(2) 0.42886(10) 0.99893(13) 0.0338(4) Uani 1 1 d . . . H20A H 0.9101 0.1243 -0.0608 0.050 Uiso 1 1 calc R . . H20E H 1.2438 0.4773 1.0322 0.051 Uiso 1 1 calc R . . H21A H 0.8305 0.0315 -0.0605 0.050 Uiso 1 1 calc R . . H21B H 1.1620 0.3848 1.0341 0.051 Uiso 1 1 calc R . . H22A H 1.0280 0.0775 -0.0198 0.050 Uiso 1 1 calc R . . H22B H 1.0423 0.4339 1.0058 0.051 Uiso 1 1 calc R . . C1G C 0.4629(2) 0.16446(11) -0.04523(16) 0.0381(5) Uani 1 1 d . . . H2G H 0.6252 0.2148 0.0901 0.047 Uiso 1 1 calc R . . C2G C 0.5603(2) 0.22574(12) 0.03316(15) 0.0390(5) Uani 1 1 d . . . C3G C 0.5653(2) 0.30204(12) 0.03059(15) 0.0388(5) Uani 1 1 d . . . C4G C 0.4701(3) 0.31682(12) -0.05206(15) 0.0411(5) Uani 1 1 d . . . H4G H 0.4711 0.3686 -0.0553 0.049 Uiso 1 1 calc R . . C5G C 0.3730(2) 0.25696(12) -0.13058(15) 0.0401(5) Uani 1 1 d . . . H5G H 0.3081 0.2680 -0.1875 0.048 Uiso 1 1 calc R . . C6G C 0.3696(2) 0.18175(12) -0.12675(15) 0.0367(5) Uani 1 1 d . . . H6G H 0.3020 0.1411 -0.1810 0.044 Uiso 1 1 calc R . . C7G C 0.4641(3) 0.08278(13) -0.0426(2) 0.0739(8) Uani 1 1 d . . . H7G1 H 0.3568 0.0450 -0.0798 0.111 Uiso 1 1 calc R . . H7G2 H 0.4772 0.0731 0.0312 0.111 Uiso 1 1 calc R . . H7G3 H 0.5593 0.0769 -0.0775 0.111 Uiso 1 1 calc R . . C8G C 0.6740(3) 0.36733(15) 0.11583(18) 0.0709(8) Uani 1 1 d . . . H8G1 H 0.7906 0.3873 0.0981 0.106 Uiso 1 1 calc R . . H8G2 H 0.6744 0.3472 0.1841 0.106 Uiso 1 1 calc R . . H8G3 H 0.6274 0.4098 0.1205 0.106 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0168(5) 0.0178(6) 0.0157(5) 0.0010(4) 0.0026(4) 0.0032(4) O1B 0.0186(5) 0.0194(6) 0.0162(6) 0.0017(5) 0.0031(5) 0.0061(5) O2A 0.0151(5) 0.0146(6) 0.0272(6) 0.0014(5) -0.0017(5) 0.0053(4) O2B 0.0155(5) 0.0166(6) 0.0303(6) 0.0019(5) -0.0016(5) 0.0050(4) O3A 0.0311(6) 0.0228(7) 0.0227(6) -0.0055(5) -0.0031(5) -0.0012(5) O3B 0.0274(6) 0.0215(6) 0.0223(6) -0.0022(5) -0.0028(5) 0.0031(5) C1A 0.0149(7) 0.0178(8) 0.0137(7) 0.0015(6) 0.0013(6) 0.0056(6) C1B 0.0153(7) 0.0193(8) 0.0156(8) 0.0018(6) 0.0012(6) 0.0061(6) C2A 0.0171(8) 0.0177(9) 0.0237(8) 0.0035(7) 0.0023(7) 0.0049(6) C2B 0.0194(8) 0.0192(9) 0.0220(8) 0.0032(7) 0.0017(7) 0.0071(7) C3A 0.0242(9) 0.0200(9) 0.0262(9) 0.0039(7) 0.0026(7) 0.0115(7) C3B 0.0233(9) 0.0229(9) 0.0243(9) 0.0044(7) 0.0028(7) 0.0132(7) C4A 0.0148(8) 0.0276(9) 0.0232(8) 0.0034(7) 0.0009(7) 0.0092(7) C4B 0.0155(8) 0.0306(10) 0.0218(8) 0.0032(7) 0.0016(7) 0.0102(7) C5A 0.0158(8) 0.0204(9) 0.0216(8) 0.0014(7) 0.0007(7) 0.0042(7) C5B 0.0158(8) 0.0226(9) 0.0211(8) 0.0006(7) 0.0006(7) 0.0043(7) C6A 0.0184(8) 0.0163(8) 0.0153(7) 0.0014(6) 0.0024(6) 0.0076(6) C6B 0.0196(8) 0.0181(9) 0.0176(8) 0.0014(6) 0.0025(7) 0.0095(7) C7A 0.0175(8) 0.0170(8) 0.0144(7) 0.0011(6) 0.0027(6) 0.0067(6) C7B 0.0179(8) 0.0193(8) 0.0143(7) 0.0005(6) 0.0023(6) 0.0089(6) C8A 0.0185(8) 0.0185(8) 0.0222(8) 0.0020(7) 0.0011(7) 0.0066(7) C8B 0.0179(8) 0.0220(9) 0.0197(8) 0.0020(7) 0.0013(7) 0.0062(7) C9A 0.0209(8) 0.0234(9) 0.0240(9) 0.0010(7) -0.0025(7) 0.0103(7) C9B 0.0231(8) 0.0272(9) 0.0219(8) 0.0013(7) -0.0012(7) 0.0129(7) C10A 0.0267(9) 0.0171(9) 0.0260(9) 0.0040(7) -0.0008(7) 0.0098(7) C10B 0.0295(9) 0.0193(9) 0.0239(9) 0.0033(7) 0.0009(7) 0.0125(7) C11A 0.0213(8) 0.0158(8) 0.0249(9) 0.0027(7) 0.0016(7) 0.0049(7) C11B 0.0247(8) 0.0179(9) 0.0259(9) 0.0025(7) 0.0032(7) 0.0068(7) C12A 0.0147(7) 0.0194(8) 0.0165(8) 0.0008(6) -0.0002(6) 0.0065(6) C12B 0.0170(8) 0.0208(9) 0.0168(8) 0.0013(6) 0.0013(7) 0.0065(7) C13A 0.0144(7) 0.0169(8) 0.0151(7) 0.0020(6) 0.0026(6) 0.0054(6) C13B 0.0159(7) 0.0179(8) 0.0152(8) 0.0020(6) 0.0025(6) 0.0058(6) C14A 0.0140(7) 0.0158(8) 0.0182(8) 0.0016(6) 0.0001(6) 0.0075(6) C14B 0.0149(7) 0.0191(8) 0.0181(8) 0.0028(6) -0.0005(6) 0.0089(6) C15A 0.0175(8) 0.0185(8) 0.0197(8) 0.0015(7) 0.0029(7) 0.0063(7) C15B 0.0190(8) 0.0223(9) 0.0164(8) 0.0032(6) 0.0019(7) 0.0096(7) C16A 0.0170(8) 0.0200(9) 0.0259(9) 0.0026(7) 0.0034(7) 0.0032(7) C16B 0.0158(8) 0.0190(8) 0.0257(9) 0.0057(7) 0.0033(7) 0.0043(6) C17A 0.0191(8) 0.0162(8) 0.0226(8) -0.0008(7) -0.0048(7) 0.0055(7) C17B 0.0184(8) 0.0163(8) 0.0222(8) 0.0009(7) -0.0039(7) 0.0082(7) C18A 0.0267(9) 0.0204(9) 0.0153(8) 0.0021(7) 0.0008(7) 0.0088(7) C18B 0.0248(8) 0.0212(9) 0.0175(8) 0.0029(7) 0.0012(7) 0.0095(7) C19A 0.0176(8) 0.0180(8) 0.0204(8) 0.0043(7) 0.0023(7) 0.0046(6) C19B 0.0197(8) 0.0196(9) 0.0234(8) 0.0072(7) 0.0035(7) 0.0067(7) C20A 0.0424(11) 0.0271(10) 0.0215(9) -0.0050(7) -0.0018(8) 0.0042(8) C20B 0.0430(11) 0.0280(10) 0.0231(9) -0.0032(8) -0.0024(8) 0.0065(8) C1G 0.0258(9) 0.0366(11) 0.0555(13) 0.0162(10) 0.0160(9) 0.0102(8) C1G 0.0258(9) 0.0366(11) 0.0555(13) 0.0162(10) 0.0160(9) 0.0102(8) C2G 0.0206(9) 0.0604(14) 0.0359(11) 0.0253(10) 0.0034(8) 0.0087(9) C3G 0.0300(10) 0.0437(12) 0.0343(11) 0.0051(9) 0.0145(9) -0.0005(9) C4G 0.0504(12) 0.0422(12) 0.0399(12) 0.0132(10) 0.0226(10) 0.0218(10) C5G 0.0399(11) 0.0633(15) 0.0297(10) 0.0123(10) 0.0075(9) 0.0317(10) C6G 0.0239(9) 0.0491(13) 0.0351(11) -0.0026(9) 0.0041(8) 0.0126(9) C7G 0.0491(14) 0.0473(15) 0.135(3) 0.0378(16) 0.0313(15) 0.0171(11) C8G 0.0484(14) 0.0843(19) 0.0471(14) -0.0124(13) 0.0166(11) -0.0160(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken "into account individually in the estimation of esds in distances, angles" and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C13A 1.4489(17) . ? O1A H1A 0.958(7) . ? O1B C13B 1.4497(17) . ? O1B H1B 0.965(7) . ? O2A C12A 1.3880(17) . ? O2A C6A 1.3904(17) . ? O2B C12B 1.3834(17) . ? O2B C6B 1.3919(17) . ? O3A C17A 1.3702(18) . ? O3A C20A 1.424(2) . ? O3B C17B 1.3732(17) . ? O3B C20B 1.4273(19) . ? C1A C2A 1.392(2) . ? C1A C6A 1.391(2) . ? C2A C3A 1.386(2) . ? C2A H2A 0.9500 . ? C2B C1B 1.393(2) . ? C2B H2B 0.9500 . ? C3A H3A 0.9500 . ? C3B C2B 1.384(2) . ? C3B C4B 1.390(2) . ? C3B H3B 0.9500 . ? C4A C3A 1.388(2) . ? C4A H4A 0.9500 . ? C4B H4B 0.9500 . ? C4G C3G 1.373(3) . ? C4G C5G 1.383(3) . ? C4G H4G 0.9500 . ? C5A C4A 1.375(2) . ? C5A H5A 0.9500 . ? C5B C4B 1.380(2) . ? C5B C6B 1.383(2) . ? C5B H5B 0.9500 . ? C5G H5G 0.9500 . ? C6A C5A 1.389(2) . ? C6B C1B 1.395(2) . ? C6G C1G 1.376(3) . ? C6G C5G 1.372(3) . ? C6G H6G 0.9500 . ? C7A C12A 1.390(2) . ? C7B C12B 1.393(2) . ? C7G H7G1 0.9800 . ? C7G H7G2 0.9800 . ? C7G H7G3 0.9800 . ? C8A C7A 1.398(2) . ? C8A C9A 1.380(2) . ? C8A H8A 0.9500 . ? C8B C7B 1.397(2) . ? C8B H8B 0.9500 . ? C8G H8G1 0.9800 . ? C8G H8G2 0.9800 . ? C8G H8G3 0.9800 . ? C9A H9A 0.9500 . ? C9B C10B 1.390(2) . ? C9B C8B 1.386(2) . ? C9B H9B 0.9500 . ? C10A C9A 1.390(2) . ? C10A H10A 0.9500 . ? C10B C11B 1.376(2) . ? C10B H10B 0.9500 . ? C11A C10A 1.380(2) . ? C11A H11A 0.9500 . ? C11B H11B 0.9500 . ? C12A C11A 1.390(2) . ? C12B C11B 1.390(2) . ? C13A C1A 1.520(2) . ? C13A C7A 1.524(2) . ? C13B C1B 1.522(2) . ? C13B C7B 1.527(2) . ? C14A C13A 1.524(2) . ? C14A C15A 1.392(2) . ? C14A C19A 1.386(2) . ? C14B C13B 1.529(2) . ? C14B C19B 1.384(2) . ? C15A H15A 0.9500 . ? C15B C14B 1.390(2) . ? C15B H15B 0.9500 . ? C16A C15A 1.384(2) . ? C16A H16A 0.9500 . ? C16B C15B 1.388(2) . ? C16B C17B 1.387(2) . ? C16B H16B 0.9500 . ? C17A C16A 1.388(2) . ? C17A C18A 1.391(2) . ? C17B C18B 1.389(2) . ? C18A H18A 0.9500 . ? C18B H18B 0.9500 . ? C19A C18A 1.387(2) . ? C19A H19A 0.9500 . ? C19B C18B 1.392(2) . ? C19B H19B 0.9500 . ? C20A H20A 0.9800 . ? C20A H21A 0.9800 . ? C20A H22A 0.9800 . ? C20B H20E 0.9800 . ? C20B H21B 0.9800 . ? C20B H22B 0.9800 . ? C1G C7G 1.501(3) . ? C2G C1G 1.396(3) . ? C2G C3G 1.385(3) . ? C2G H2G 0.9500 . ? C3G C8G 1.512(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1A C13A C14A 106.48(11) . . ? O1A C13A C1A 109.02(11) . . ? O1A C13A C7A 108.84(12) . . ? O1B C13B C14B 106.22(11) . . ? O1B C13B C1B 108.33(11) . . ? O1B C13B C7B 108.39(12) . . ? O2A C12A C11A 115.42(12) . . ? O2A C12A C7A 122.35(13) . . ? O2A C6A C1A 122.05(13) . . ? O2B C12B C11B 115.27(13) . . ? O2B C12B C7B 122.61(13) . . ? O2B C6B C1B 122.20(13) . . ? O3A C17A C16A 115.83(14) . . ? O3A C17A C18A 124.10(14) . . ? O3A C20A H20A 109.5 . . ? O3A C20A H21A 109.5 . . ? O3A C20A H22A 109.5 . . ? O3B C17B C16B 115.55(13) . . ? O3B C17B C18B 124.88(14) . . ? O3B C20B H20E 109.5 . . ? O3B C20B H21B 109.5 . . ? O3B C20B H22B 109.5 . . ? C1A C13A C14A 111.65(12) . . ? C1A C13A C7A 109.52(11) . . ? C1A C2A H2A 119.2 . . ? C1B C13B C14B 112.36(13) . . ? C1B C13B C7B 109.54(12) . . ? C1B C2B H2B 119.2 . . ? C2A C1A C13A 121.75(13) . . ? C2A C3A C4A 119.68(15) . . ? C2A C3A H3A 120.2 . . ? C2B C1B C13B 121.56(13) . . ? C2B C1B C6B 116.92(13) . . ? C2B C3B C4B 119.89(15) . . ? C2B C3B H3B 120.1 . . ? C3A C2A C1A 121.61(14) . . ? C3A C2A H2A 119.2 . . ? C3A C4A H4A 119.9 . . ? C3B C2B C1B 121.57(14) . . ? C3B C2B H2B 119.2 . . ? C3B C4B H4B 120.1 . . ? C4A C3A H3A 120.2 . . ? C4A C5A C6A 119.16(14) . . ? C4A C5A H5A 120.4 . . ? C4B C3B H3B 120.1 . . ? C4B C5B C6B 119.44(14) . . ? C4B C5B H5B 120.3 . . ? C5A C4A C3A 120.19(14) . . ? C5A C4A H4A 119.9 . . ? C5A C6A C1A 122.35(14) . . ? C5A C6A O2A 115.60(12) . . ? C5B C4B C3B 119.81(14) . . ? C5B C4B H4B 120.1 . . ? C5B C6B C1B 122.29(14) . . ? C5B C6B O2B 115.50(13) . . ? C6A C1A C13A 121.07(13) . . ? C6A C1A C2A 116.96(13) . . ? C6A C5A H5A 120.4 . . ? C6B C1B C13B 121.20(13) . . ? C6B C5B H5B 120.3 . . ? C7A C13A C14A 111.23(11) . . ? C7A C8A H8A 119.2 . . ? C7B C13B C14B 111.82(11) . . ? C7B C8B H8B 119.1 . . ? C8A C7A C13A 121.90(13) . . ? C8A C9A C10A 119.89(14) . . ? C8A C9A H9A 120.1 . . ? C8B C7B C13B 121.71(13) . . ? C8B C9B C10B 119.56(15) . . ? C8B C9B H9B 120.2 . . ? C9A C10A H10A 120.0 . . ? C9A C8A C7A 121.60(14) . . ? C9A C8A H8A 119.2 . . ? C9B C10B H10B 120.0 . . ? C9B C8B C7B 121.85(14) . . ? C9B C8B H8B 119.1 . . ? C10A C11A C12A 119.24(14) . . ? C10A C11A H11A 120.4 . . ? C10A C9A H9A 120.1 . . ? C10B C11B C12B 119.56(14) . . ? C10B C11B H11B 120.2 . . ? C10B C9B H9B 120.2 . . ? C11A C10A C9A 119.99(15) . . ? C11A C10A H10A 120.0 . . ? C11A C12A C7A 122.23(14) . . ? C11B C10B C9B 120.04(15) . . ? C11B C10B H10B 120.0 . . ? C11B C12B C7B 122.12(14) . . ? C12A C11A H11A 120.4 . . ? C12A C7A C13A 120.91(13) . . ? C12A C7A C8A 117.04(14) . . ? C12A O2A C6A 118.29(11) . . ? C12B C11B H11B 120.2 . . ? C12B C7B C13B 121.18(13) . . ? C12B C7B C8B 116.85(14) . . ? C12B O2B C6B 118.56(11) . . ? C13A O1A H1A 108.3(11) . . ? C13B O1B H1B 108.0(12) . . ? C14A C15A H15A 119.7 . . ? C14A C19A C18A 121.90(14) . . ? C14A C19A H19A 119.1 . . ? C14B C15B H15B 119.7 . . ? C14B C19B C18B 121.86(14) . . ? C14B C19B H19B 119.1 . . ? C15A C14A C13A 122.46(13) . . ? C15A C16A C17A 120.19(14) . . ? C15A C16A H16A 119.9 . . ? C15B C14B C13B 121.90(13) . . ? C15B C16B H16B 119.8 . . ? C16A C15A C14A 120.64(14) . . ? C16A C15A H15A 119.7 . . ? C16A C17A C18A 120.05(14) . . ? C16B C15B C14B 120.68(14) . . ? C16B C15B H15B 119.7 . . ? C16B C17B C18B 119.57(14) . . ? C17A C16A H16A 119.9 . . ? C17A C18A H18A 120.6 . . ? C17A O3A C20A 117.06(12) . . ? C17B C16B C15B 120.44(14) . . ? C17B C16B H16B 119.8 . . ? C17B C18B C19B 119.21(14) . . ? C17B C18B H18B 120.4 . . ? C17B O3B C20B 117.20(12) . . ? C18A C19A H19A 119.1 . . ? C18B C19B H19B 119.1 . . ? C19A C14A C13A 119.18(13) . . ? C19A C14A C15A 118.35(14) . . ? C19A C18A C17A 118.86(14) . . ? C19A C18A H18A 120.6 . . ? C19B C14B C13B 119.89(13) . . ? C19B C14B C15B 118.21(14) . . ? C19B C18B H18B 120.4 . . ? H20A C20A H21A 109.5 . . ? H20A C20A H22A 109.5 . . ? H20E C20B H21B 109.5 . . ? H21A C20A H22A 109.5 . . ? H22B C20B H20E 109.5 . . ? H22B C20B H21B 109.5 . . ? C1G C2G H2G 118.9 . . ? C1G C6G H6G 119.6 . . ? C1G C7G H7G1 109.5 . . ? C1G C7G H7G2 109.5 . . ? C1G C7G H7G3 109.5 . . ? C2G C1G C7G 121.12(19) . . ? C2G C3G C8G 120.86(19) . . ? C3G C2G C1G 122.13(16) . . ? C3G C2G H2G 118.9 . . ? C3G C4G C5G 120.61(19) . . ? C3G C4G H4G 119.7 . . ? C3G C8G H8G1 109.5 . . ? C3G C8G H8G2 109.5 . . ? C3G C8G H8G3 109.5 . . ? C4G C3G C2G 118.17(17) . . ? C4G C3G C8G 121.0(2) . . ? C4G C5G H5G 119.8 . . ? C5G C4G H4G 119.7 . . ? C5G C6G C1G 120.79(18) . . ? C5G C6G H6G 119.6 . . ? C6G C1G C2G 117.88(18) . . ? C6G C1G C7G 121.0(2) . . ? C6G C5G C4G 120.42(18) . . ? C6G C5G H5G 119.8 . . ? H7G1 C7G H7G2 109.5 . . ? H7G1 C7G H7G3 109.5 . . ? H7G2 C7G H7G3 109.5 . . ? H8G1 C8G H8G2 109.5 . . ? H8G1 C8G H8G3 109.5 . . ? H8G2 C8G H8G3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C13A C1A C2A 78.75(17) . . . . ? O1A C13A C1A C6A -95.75(15) . . . . ? O1A C13A C7A C12A 97.30(15) . . . . ? O1A C13A C7A C8A -78.05(16) . . . . ? O1B C13B C1B C2B -77.17(17) . . . . ? O1B C13B C1B C6B 96.15(16) . . . . ? O1B C13B C7B C12B -97.84(16) . . . . ? O1B C13B C7B C8B 76.21(16) . . . . ? O2A C12A C11A C10A -179.01(14) . . . . ? O2A C6A C5A C4A -179.84(13) . . . . ? O2B C12B C11B C10B 177.84(14) . . . . ? O2B C6B C1B C13B 8.2(2) . . . . ? O2B C6B C1B C2B -178.17(13) . . . . ? O3A C17A C16A C15A 178.13(13) . . . . ? O3A C17A C18A C19A -178.22(14) . . . . ? O3B C17B C18B C19B -179.67(14) . . . . ? C1A C13A C7A C12A -21.80(19) . . . . ? C1A C13A C7A C8A 162.85(14) . . . . ? C1A C2A C3A C4A -0.2(2) . . . . ? C1A C6A C5A C4A 0.1(2) . . . . ? C1B C13B C7B C12B 20.17(19) . . . . ? C1B C13B C7B C8B -165.78(14) . . . . ? C2A C1A C6A C5A -1.8(2) . . . . ? C2A C1A C6A O2A 178.07(13) . . . . ? C2B C3B C4B C5B 2.1(2) . . . . ? C3B C2B C1B C13B 171.25(14) . . . . ? C3B C2B C1B C6B -2.3(2) . . . . ? C4B C3B C2B C1B 0.1(2) . . . . ? C4B C5B C6B C1B -0.4(2) . . . . ? C4B C5B C6B O2B -179.77(13) . . . . ? C5A C4A C3A C2A -1.6(2) . . . . ? C5B C6B C1B C13B -171.08(14) . . . . ? C5B C6B C1B C2B 2.5(2) . . . . ? C6A C1A C2A C3A 1.9(2) . . . . ? C6A C5A C4A C3A 1.7(2) . . . . ? C6A O2A C12A C11A -165.75(13) . . . . ? C6A O2A C12A C7A 14.6(2) . . . . ? C6B C5B C4B C3B -2.0(2) . . . . ? C6B O2B C12B C11B 168.97(13) . . . . ? C6B O2B C12B C7B -11.8(2) . . . . ? C7A C12A C11A C10A 0.6(2) . . . . ? C7A C13A C1A C2A -162.26(13) . . . . ? C7A C13A C1A C6A 23.24(19) . . . . ? C7A C8A C9A C10A 1.4(2) . . . . ? C7B C12B C11B C10B -1.4(2) . . . . ? C7B C13B C1B C2B 164.78(13) . . . . ? C7B C13B C1B C6B -21.90(19) . . . . ? C8A C7A C12A C11A 0.2(2) . . . . ? C8A C7A C12A O2A 179.81(13) . . . . ? C8B C7B C12B C11B 0.2(2) . . . . ? C8B C7B C12B O2B -178.90(13) . . . . ? C8B C9B C10B C11B -0.1(2) . . . . ? C9A C8A C7A C12A -1.2(2) . . . . ? C9A C8A C7A C13A 174.30(14) . . . . ? C9B C10B C11B C12B 1.3(2) . . . . ? C9B C8B C7B C12B 1.0(2) . . . . ? C9B C8B C7B C13B -173.30(14) . . . . ? C10B C9B C8B C7B -1.1(2) . . . . ? C11A C10A C9A C8A -0.5(2) . . . . ? C12A C11A C10A C9A -0.4(2) . . . . ? C12A O2A C6A C1A -13.1(2) . . . . ? C12A O2A C6A C5A 166.78(13) . . . . ? C12B O2B C6B C1B 10.0(2) . . . . ? C12B O2B C6B C5B -170.66(13) . . . . ? C13A C14A C15A C16A 179.41(14) . . . . ? C13A C14A C19A C18A -179.65(14) . . . . ? C13A C1A C2A C3A -172.82(14) . . . . ? C13A C1A C6A C5A 172.92(13) . . . . ? C13A C1A C6A O2A -7.2(2) . . . . ? C13A C7A C12A C11A -175.36(14) . . . . ? C13A C7A C12A O2A 4.2(2) . . . . ? C13B C14B C19B C18B 178.87(14) . . . . ? C13B C7B C12B C11B 174.56(14) . . . . ? C13B C7B C12B O2B -4.6(2) . . . . ? C14A C13A C1A C2A -38.61(18) . . . . ? C14A C13A C1A C6A 146.89(14) . . . . ? C14A C13A C7A C12A -145.70(14) . . . . ? C14A C13A C7A C8A 38.95(19) . . . . ? C14A C19A C18A C17A 0.2(2) . . . . ? C14B C13B C1B C2B 39.86(19) . . . . ? C14B C13B C1B C6B -146.82(14) . . . . ? C14B C13B C7B C12B 145.41(14) . . . . ? C14B C13B C7B C8B -40.54(19) . . . . ? C14B C19B C18B C17B 0.6(2) . . . . ? C15A C14A C13A C1A 121.35(15) . . . . ? C15A C14A C13A C7A -115.98(15) . . . . ? C15A C14A C13A O1A 2.46(18) . . . . ? C15A C14A C19A C18A -0.2(2) . . . . ? C15B C14B C13B C1B -114.93(15) . . . . ? C15B C14B C13B C7B 121.40(15) . . . . ? C15B C14B C13B O1B 3.35(18) . . . . ? C15B C14B C19B C18B -1.5(2) . . . . ? C15B C16B C17B C18B -1.6(2) . . . . ? C15B C16B C17B O3B 178.99(13) . . . . ? C16A C17A C18A C19A 0.1(2) . . . . ? C16B C15B C14B C13B -179.50(14) . . . . ? C16B C15B C14B C19B 0.9(2) . . . . ? C16B C17B C18B C19B 1.0(2) . . . . ? C17A C16A C15A C14A 0.3(2) . . . . ? C17B C16B C15B C14B 0.7(2) . . . . ? C18A C17A C16A C15A -0.3(2) . . . . ? C19A C14A C13A C1A -59.24(17) . . . . ? C19A C14A C13A C7A 63.43(18) . . . . ? C19A C14A C13A O1A -178.13(13) . . . . ? C19A C14A C15A C16A 0.0(2) . . . . ? C19B C14B C13B C1B 64.69(17) . . . . ? C19B C14B C13B C7B -58.98(18) . . . . ? C19B C14B C13B O1B -177.03(13) . . . . ? C20A O3A C17A C16A -179.02(15) . . . . ? C20A O3A C17A C18A -0.7(2) . . . . ? C20B O3B C17B C16B 179.17(14) . . . . ? C20B O3B C17B C18B -0.2(2) . . . . ? C1G C2G C3G C4G 0.3(3) . . . . ? C1G C2G C3G C8G -179.07(18) . . . . ? C1G C6G C5G C4G -0.2(3) . . . . ? C3G C2G C1G C6G -0.2(3) . . . . ? C3G C2G C1G C7G 177.95(18) . . . . ? C3G C4G C5G C6G 0.3(3) . . . . ? C5G C4G C3G C2G -0.3(3) . . . . ? C5G C4G C3G C8G 179.03(18) . . . . ? C5G C6G C1G C2G 0.2(3) . . . . ? C5G C6G C1G C7G -177.97(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1A O2A 0.958(7) 1.894(7) 2.8509(14) 177.0(17) 2_866 O1B H1B O2B 0.965(7) 1.916(7) 2.8809(14) 177.4(18) 2_656 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.246 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.054 _chemical_name_common '9-(4-methoxyphenyl)-9H-xanthen-9-ol m-xylene clathrate'