data_global _publ_contact_author_email XRAYLUIG@SCIENCE.UCT.AC.ZA _publ_contact_author_name 'Prof Luigi Nassimbeni' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_address ; Chemistry University of Cape Town Rondebosch Cape Town South Africa 7701 ; _publ_section_title ; Inclusion of quinolines by binaphthol: structures and selectivity ; loop_ _publ_author_name 'Luigi Nassimbeni' 'Mino R. Caira' 'Y.Paul Chang' 'Hong Su' data_c_bnpq _database_code_depnum_ccdc_archive 'CCDC 224350' _chemical_name_common '2,2’-dihydroxyl-1,1’-binaphthyl diquinoline' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2’-dihydroxyl-1,1’-binaphthyl diquinoline ; _chemical_melting_point ? _chemical_formula_moiety C20H14O22C9H7N1 _chemical_formula_sum 'C38 H28 N2 O2' _chemical_formula_weight 544.62 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' N N 0.0061 0.0033 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.1633(8) _cell_length_b 11.0249(5) _cell_length_c 14.0928(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.171(2) _cell_angle_gamma 90.00 _cell_volume 2800.0(2) _cell_formula_units_Z 4 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_min 0.9889 _exptl_absorpt_correction_T_max 0.9921 _exptl_special_details ; Complete half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 35 mm; combination of \f and \w scans of 1.0\%, 60s per \%, 2 iterations. ; _diffrn_ambient_temperature 203(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 '1.0\% \f scans and \w scans' _diffrn_reflns_number 5175 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.14 _reflns_number_total 3064 _reflns_number_gt 1668 _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-86 (Sheldrick, 1986)' _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^)+(0.0451P)^2^+0.8610P] 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 3064 _refine_ls_number_parameters 189 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1264 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.016 _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 0.47260(8) 0.78976(13) 0.37095(11) 0.0506(4) Uani 1 1 d D . . C1 C 0.45881(9) 0.64266(15) 0.25022(13) 0.0286(4) Uani 1 1 d . . . H1 H 0.4484(16) 0.850(2) 0.4074(19) 0.119(11) Uiso 1 1 d D . . C9 C 0.33507(10) 0.56238(16) 0.19074(15) 0.0348(5) Uani 1 1 d . . . C10 C 0.41287(10) 0.56434(15) 0.18776(14) 0.0299(5) Uani 1 1 d . . . C8 C 0.44240(11) 0.48712(16) 0.12172(14) 0.0354(5) Uani 1 1 d . . . H8 H 0.4938 0.4878 0.1185 0.043 Uiso 1 1 calc R . . C5 C 0.29073(11) 0.48250(18) 0.12896(17) 0.0463(6) Uani 1 1 d . . . H5 H 0.2392 0.4806 0.1309 0.056 Uiso 1 1 calc R . . C2 C 0.42681(11) 0.71776(16) 0.31149(14) 0.0339(5) Uiso 1 1 d . . . N1G N 0.40754(9) 0.96350(15) 0.47010(13) 0.0427(5) Uani 1 1 d D . . C3 C 0.34939(11) 0.71662(18) 0.31332(15) 0.0386(5) Uani 1 1 d . . . H3 H 0.3283 0.7686 0.3554 0.046 Uiso 1 1 calc R . . C4 C 0.30481(11) 0.64170(17) 0.25533(15) 0.0400(5) Uani 1 1 d . . . H4 H 0.2533 0.6422 0.2579 0.048 Uiso 1 1 calc R . . C10G C 0.39890(10) 1.07968(18) 0.43550(14) 0.0342(5) Uani 1 1 d . . . C9G C 0.36580(10) 1.17110(17) 0.48600(14) 0.0349(5) Uani 1 1 d . . . C7 C 0.39814(12) 0.41167(17) 0.06253(16) 0.0447(6) Uani 1 1 d . . . H7 H 0.4191 0.3618 0.0189 0.054 Uiso 1 1 calc R . . C6 C 0.32084(12) 0.40851(19) 0.06684(18) 0.0528(7) Uani 1 1 d . . . H6 H 0.2904 0.3556 0.0270 0.063 Uiso 1 1 calc R . . C4G C 0.34310(12) 1.14019(19) 0.57427(15) 0.0453(6) Uani 1 1 d . . . H4G H 0.3215 1.1992 0.6102 0.054 Uiso 1 1 calc R . . C3G C 0.35228(13) 1.0256(2) 0.60774(16) 0.0501(6) Uani 1 1 d . . . H3G H 0.3370 1.0038 0.6667 0.060 Uiso 1 1 calc R . . C2G C 0.38494(13) 0.94038(19) 0.55294(17) 0.0490(6) Uani 1 1 d . . . H2G H 0.3911 0.8611 0.5771 0.059 Uiso 1 1 calc R . . C5G C 0.35672(13) 1.28849(19) 0.44580(18) 0.0510(6) Uani 1 1 d . . . H5G H 0.3350 1.3502 0.4790 0.061 Uiso 1 1 calc R . . C8G C 0.42278(12) 1.1081(2) 0.34660(16) 0.0544(6) Uani 1 1 d . . . H8G H 0.4458 1.0485 0.3127 0.065 Uiso 1 1 calc R . . C6G C 0.37911(14) 1.3122(2) 0.3601(2) 0.0650(8) Uani 1 1 d . . . H6G H 0.3723 1.3903 0.3336 0.078 Uiso 1 1 calc R . . C7G C 0.41237(14) 1.2219(3) 0.31003(19) 0.0681(8) Uani 1 1 d . . . H7G H 0.4277 1.2402 0.2504 0.082 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 0.0373(9) 0.0526(10) 0.0611(11) -0.0220(8) 0.0031(7) 0.0064(7) C1 0.0250(10) 0.0252(9) 0.0359(11) 0.0047(8) 0.0048(8) 0.0010(8) C9 0.0283(11) 0.0285(10) 0.0465(13) 0.0151(9) 0.0005(9) -0.0034(8) C10 0.0281(10) 0.0234(9) 0.0376(12) 0.0070(8) 0.0015(9) -0.0018(8) C8 0.0323(11) 0.0282(10) 0.0449(13) 0.0001(9) 0.0010(9) -0.0015(8) C5 0.0292(11) 0.0387(12) 0.0680(16) 0.0168(11) -0.0057(11) -0.0056(10) N1G 0.0394(10) 0.0371(10) 0.0501(12) -0.0079(9) -0.0003(9) 0.0068(8) C3 0.0304(11) 0.0406(11) 0.0463(13) 0.0060(10) 0.0110(9) 0.0106(9) C4 0.0269(10) 0.0399(11) 0.0540(14) 0.0172(10) 0.0077(10) 0.0050(9) C10G 0.0259(10) 0.0408(11) 0.0352(12) -0.0043(9) 0.0019(9) -0.0021(8) C9G 0.0336(11) 0.0338(10) 0.0366(12) -0.0042(9) 0.0017(9) -0.0054(9) C7 0.0509(14) 0.0308(11) 0.0498(14) -0.0041(10) -0.0032(11) 0.0001(10) C6 0.0499(15) 0.0335(12) 0.0694(18) -0.0003(11) -0.0154(13) -0.0109(11) C4G 0.0505(14) 0.0431(13) 0.0434(14) -0.0143(10) 0.0096(11) -0.0018(10) C3G 0.0621(15) 0.0528(14) 0.0365(13) -0.0008(10) 0.0108(11) -0.0108(12) C2G 0.0590(15) 0.0349(11) 0.0509(15) 0.0047(11) -0.0019(12) -0.0021(10) C5G 0.0527(14) 0.0360(12) 0.0608(17) 0.0022(11) -0.0061(12) -0.0046(10) C8G 0.0360(13) 0.0860(19) 0.0418(15) -0.0044(13) 0.0072(11) -0.0051(12) C6G 0.0604(16) 0.0581(16) 0.071(2) 0.0261(14) -0.0133(14) -0.0206(14) C7G 0.0515(16) 0.108(2) 0.0434(16) 0.0233(16) -0.0005(12) -0.0260(16) _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 C2 1.360(2) . ? O1 H1 0.975(7) . ? C1 C2 1.376(3) . ? C1 C10 1.426(2) . ? C1 C1 1.497(3) 2_655 ? C9 C5 1.417(3) . ? C9 C10 1.419(2) . ? C9 C4 1.421(3) . ? C10 C8 1.415(3) . ? C8 C7 1.366(3) . ? C8 H8 0.9400 . ? C5 C6 1.360(3) . ? C5 H5 0.9400 . ? C2 C3 1.410(3) . ? N1G C2G 1.310(3) . ? N1G C10G 1.373(3) . ? C3 C4 1.357(3) . ? C3 H3 0.9400 . ? C4 H4 0.9400 . ? C10G C9G 1.411(3) . ? C10G C8G 1.411(3) . ? C9G C4G 1.401(3) . ? C9G C5G 1.414(3) . ? C7 C6 1.413(3) . ? C7 H7 0.9400 . ? C6 H6 0.9400 . ? C4G C3G 1.352(3) . ? C4G H4G 0.9400 . ? C3G C2G 1.395(3) . ? C3G H3G 0.9400 . ? C2G H2G 0.9400 . ? C5G C6G 1.348(3) . ? C5G H5G 0.9400 . ? C8G C7G 1.361(3) . ? C8G H8G 0.9400 . ? C6G C7G 1.400(4) . ? C6G H6G 0.9400 . ? C7G H7G 0.9400 . ? 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 C2 O1 H1 116.0(19) . . ? C2 C1 C10 119.41(17) . . ? C2 C1 C1 120.21(17) . 2_655 ? C10 C1 C1 120.37(16) . 2_655 ? C5 C9 C10 118.88(19) . . ? C5 C9 C4 122.72(19) . . ? C10 C9 C4 118.40(18) . . ? C8 C10 C9 118.08(17) . . ? C8 C10 C1 121.98(17) . . ? C9 C10 C1 119.94(17) . . ? C7 C8 C10 121.70(19) . . ? C7 C8 H8 119.2 . . ? C10 C8 H8 119.2 . . ? C6 C5 C9 121.7(2) . . ? C6 C5 H5 119.2 . . ? C9 C5 H5 119.2 . . ? O1 C2 C1 117.63(17) . . ? O1 C2 C3 121.91(18) . . ? C1 C2 C3 120.43(18) . . ? C2G N1G C10G 117.61(18) . . ? C4 C3 C2 121.07(19) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C9 120.73(19) . . ? C3 C4 H4 119.6 . . ? C9 C4 H4 119.6 . . ? N1G C10G C9G 121.64(18) . . ? N1G C10G C8G 119.2(2) . . ? C9G C10G C8G 119.1(2) . . ? C4G C9G C10G 117.73(18) . . ? C4G C9G C5G 123.1(2) . . ? C10G C9G C5G 119.17(19) . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C3G C4G C9G 120.0(2) . . ? C3G C4G H4G 120.0 . . ? C9G C4G H4G 120.0 . . ? C4G C3G C2G 118.6(2) . . ? C4G C3G H3G 120.7 . . ? C2G C3G H3G 120.7 . . ? N1G C2G C3G 124.4(2) . . ? N1G C2G H2G 117.8 . . ? C3G C2G H2G 117.8 . . ? C6G C5G C9G 120.2(2) . . ? C6G C5G H5G 119.9 . . ? C9G C5G H5G 119.9 . . ? C7G C8G C10G 119.8(2) . . ? C7G C8G H8G 120.1 . . ? C10G C8G H8G 120.1 . . ? C5G C6G C7G 120.7(2) . . ? C5G C6G H6G 119.6 . . ? C7G C6G H6G 119.6 . . ? C8G C7G C6G 120.9(2) . . ? C8G C7G H7G 119.6 . . ? C6G C7G H7G 119.6 . . ? 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 C5 C9 C10 C8 0.9(3) . . . . ? C4 C9 C10 C8 -178.58(17) . . . . ? C5 C9 C10 C1 -179.08(17) . . . . ? C4 C9 C10 C1 1.4(3) . . . . ? C2 C1 C10 C8 178.56(17) . . . . ? C1 C1 C10 C8 -1.9(3) 2_655 . . . ? C2 C1 C10 C9 -1.4(3) . . . . ? C1 C1 C10 C9 178.11(17) 2_655 . . . ? C9 C10 C8 C7 -0.5(3) . . . . ? C1 C10 C8 C7 179.53(17) . . . . ? C10 C9 C5 C6 -0.4(3) . . . . ? C4 C9 C5 C6 179.1(2) . . . . ? C10 C1 C2 O1 179.03(16) . . . . ? C1 C1 C2 O1 -0.5(3) 2_655 . . . ? C10 C1 C2 C3 0.6(3) . . . . ? C1 C1 C2 C3 -178.92(17) 2_655 . . . ? O1 C2 C3 C4 -178.13(18) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C9 -0.2(3) . . . . ? C5 C9 C4 C3 179.92(18) . . . . ? C10 C9 C4 C3 -0.6(3) . . . . ? C2G N1G C10G C9G -1.0(3) . . . . ? C2G N1G C10G C8G 179.83(19) . . . . ? N1G C10G C9G C4G 1.2(3) . . . . ? C8G C10G C9G C4G -179.63(18) . . . . ? N1G C10G C9G C5G -178.49(18) . . . . ? C8G C10G C9G C5G 0.6(3) . . . . ? C10 C8 C7 C6 -0.6(3) . . . . ? C9 C5 C6 C7 -0.7(3) . . . . ? C8 C7 C6 C5 1.2(3) . . . . ? C10G C9G C4G C3G -0.9(3) . . . . ? C5G C9G C4G C3G 178.8(2) . . . . ? C9G C4G C3G C2G 0.4(3) . . . . ? C10G N1G C2G C3G 0.5(3) . . . . ? C4G C3G C2G N1G -0.2(3) . . . . ? C4G C9G C5G C6G -179.4(2) . . . . ? C10G C9G C5G C6G 0.4(3) . . . . ? N1G C10G C8G C7G 177.9(2) . . . . ? C9G C10G C8G C7G -1.3(3) . . . . ? C9G C5G C6G C7G -0.7(3) . . . . ? C10G C8G C7G C6G 0.9(3) . . . . ? C5G C6G C7G C8G 0.1(4) . . . . ? 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 N1G 0.98(3) 1.75(3) 2.726(2) 177(2) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.194 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.041 #===END data_c:BINAP.2(2MeQ) _database_code_depnum_ccdc_archive 'CCDC 224351' _chemical_name_common '2,2-dihydroxyl-1,1’-binaphthyl di-2-methylquinoline' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2-dihydroxyl-1,1’-binaphthyl di-2-methylquinoline ; _chemical_melting_point ? _chemical_formula_moiety C20H14O22C10H9N1 _chemical_formula_sum 'C40 H32 N2 O2' _chemical_formula_weight 572.68 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' N N 0.0061 0.0033 '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 Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 14.8402(3) _cell_length_b 10.5377(2) _cell_length_c 9.7304(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.4430(10) _cell_angle_gamma 90.00 _cell_volume 1501.04(5) _cell_formula_units_Z 2 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_min 0.9808 _exptl_absorpt_correction_T_max 0.9946 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 32mm; combination of \f and \w scans of 1.0\%, 40s per \%, 2 iterations. ; _diffrn_ambient_temperature 203(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 '1.0\% \f scans and \w scans' _diffrn_reflns_number 6421 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3420 _reflns_number_gt 2538 _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-86 (Sheldrick, 1986)' _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^)+(0.0483P)^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 N/A _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.6(13) _refine_ls_number_reflns 3420 _refine_ls_number_parameters 204 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _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 C1 C 0.02990(10) 0.38199(13) 0.94511(15) 0.0262(3) Uani 1 1 d . . . C9 C 0.15976(10) 0.29521(15) 0.84486(15) 0.0308(4) Uani 1 1 d . . . C10 C 0.10264(10) 0.29297(14) 0.94942(15) 0.0273(3) Uani 1 1 d . . . N1G N -0.03704(9) 0.77800(13) 0.70216(14) 0.0345(3) Uani 1 1 d D . . C6 C 0.24610(12) 0.11567(16) 0.95460(17) 0.0412(4) Uani 1 1 d . . . H6 H 0.2936 0.0563 0.9566 0.049 Uiso 1 1 calc R . . C10G C -0.10166(11) 0.81723(14) 0.59294(15) 0.0317(4) Uani 1 1 d . . . C8 C 0.12098(10) 0.19999(14) 1.05536(15) 0.0323(4) Uani 1 1 d . . . H8 H 0.0851 0.1979 1.1264 0.039 Uiso 1 1 calc R . . C9G C -0.11418(11) 0.94657(15) 0.55628(16) 0.0347(4) Uani 1 1 d . . . C3 C 0.07219(12) 0.47177(16) 0.73496(17) 0.0387(4) Uani 1 1 d . . . H3 H 0.0616 0.5321 0.6629 0.046 Uiso 1 1 calc R . . C2 C 0.01529(10) 0.46937(14) 0.83824(15) 0.0314(4) Uani 1 1 d . . . C7 C 0.18955(11) 0.11320(16) 1.05690(18) 0.0396(4) Uani 1 1 d . . . H7 H 0.1989 0.0512 1.1272 0.047 Uiso 1 1 calc R . . C5 C 0.23145(10) 0.20511(16) 0.85233(17) 0.0382(4) Uani 1 1 d . . . H5 H 0.2700 0.2072 0.7847 0.046 Uiso 1 1 calc R . . C4 C 0.14243(12) 0.38712(16) 0.73895(17) 0.0389(4) Uani 1 1 d . . . H4 H 0.1798 0.3904 0.6698 0.047 Uiso 1 1 calc R . . C2G C 0.01663(11) 0.86450(16) 0.77369(16) 0.0356(4) Uani 1 1 d . . . C4G C -0.05610(12) 1.03531(16) 0.63564(17) 0.0416(4) Uani 1 1 d . . . H4G H -0.0622 1.1224 0.6152 0.050 Uiso 1 1 calc R . . C3G C 0.00850(12) 0.99459(16) 0.74141(17) 0.0399(4) Uani 1 1 d . . . H3G H 0.0479 1.0534 0.7933 0.048 Uiso 1 1 calc R . . C5G C -0.18249(12) 0.97931(19) 0.44289(17) 0.0459(5) Uani 1 1 d . . . H5G H -0.1914 1.0650 0.4172 0.055 Uiso 1 1 calc R . . C8G C -0.15673(12) 0.72530(16) 0.51539(18) 0.0407(4) Uani 1 1 d . . . H8G H -0.1484 0.6390 0.5383 0.049 Uiso 1 1 calc R . . C7G C -0.22244(13) 0.7607(2) 0.40680(18) 0.0507(5) Uani 1 1 d . . . H7G H -0.2592 0.6985 0.3560 0.061 Uiso 1 1 calc R . . C6G C -0.23547(13) 0.8886(2) 0.37049(19) 0.0530(5) Uani 1 1 d . . . H6G H -0.2810 0.9119 0.2958 0.064 Uiso 1 1 calc R . . O1 O -0.05579(8) 0.55148(10) 0.83261(12) 0.0426(3) Uani 1 1 d D . . C11G C 0.08802(13) 0.81799(19) 0.89020(18) 0.0495(5) Uani 1 1 d . . . H11A H 0.0729 0.7326 0.9160 0.074 Uiso 1 1 calc R . . H11B H 0.0902 0.8737 0.9700 0.074 Uiso 1 1 calc R . . H11C H 0.1471 0.8175 0.8599 0.074 Uiso 1 1 calc R . . H1 H -0.0476(14) 0.6240(11) 0.7739(18) 0.064(6) 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 C1 0.0244(8) 0.0263(7) 0.0286(8) -0.0026(6) 0.0068(6) -0.0008(6) C9 0.0261(8) 0.0338(8) 0.0338(8) -0.0093(7) 0.0086(6) -0.0051(7) C10 0.0242(8) 0.0272(7) 0.0304(7) -0.0059(6) 0.0039(6) -0.0036(6) N1G 0.0332(8) 0.0369(7) 0.0335(7) 0.0050(6) 0.0058(6) 0.0030(6) C6 0.0301(9) 0.0425(10) 0.0488(10) -0.0155(8) 0.0003(8) 0.0086(7) C10G 0.0319(9) 0.0358(9) 0.0290(8) 0.0037(7) 0.0095(7) 0.0030(7) C8 0.0302(8) 0.0354(8) 0.0313(8) -0.0015(7) 0.0049(6) 0.0028(7) C9G 0.0357(9) 0.0379(9) 0.0323(8) 0.0064(7) 0.0104(7) 0.0063(8) C3 0.0447(10) 0.0383(9) 0.0350(8) 0.0068(8) 0.0119(7) -0.0035(8) C2 0.0279(8) 0.0314(8) 0.0355(8) 0.0025(7) 0.0070(7) 0.0000(7) C7 0.0352(9) 0.0389(9) 0.0418(9) -0.0038(8) -0.0019(8) 0.0066(7) C5 0.0265(8) 0.0477(10) 0.0417(10) -0.0167(9) 0.0095(7) -0.0041(8) C4 0.0387(10) 0.0443(10) 0.0376(9) -0.0034(8) 0.0177(8) -0.0070(8) C2G 0.0347(9) 0.0417(10) 0.0316(9) 0.0020(7) 0.0089(7) 0.0012(8) C4G 0.0514(11) 0.0310(9) 0.0447(10) 0.0023(8) 0.0145(9) 0.0030(8) C3G 0.0427(10) 0.0369(10) 0.0401(9) -0.0062(8) 0.0070(8) -0.0025(8) C5G 0.0446(11) 0.0517(11) 0.0417(10) 0.0135(9) 0.0081(8) 0.0140(9) C8G 0.0421(10) 0.0428(10) 0.0376(9) 0.0010(8) 0.0073(8) -0.0051(8) C7G 0.0434(11) 0.0691(14) 0.0385(10) -0.0024(9) 0.0038(8) -0.0098(10) C6G 0.0404(11) 0.0813(15) 0.0353(10) 0.0115(10) 0.0003(9) 0.0070(10) O1 0.0403(7) 0.0382(6) 0.0514(7) 0.0148(5) 0.0140(6) 0.0092(6) C11G 0.0455(11) 0.0579(12) 0.0419(10) 0.0080(9) -0.0023(9) -0.0003(9) _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 C1 C2 1.379(2) . ? C1 C10 1.4254(19) . ? C1 C1 1.497(3) 2_557 ? C9 C4 1.407(2) . ? C9 C5 1.419(2) . ? C9 C10 1.4273(19) . ? C10 C8 1.416(2) . ? N1G C2G 1.330(2) . ? N1G C10G 1.373(2) . ? C6 C5 1.362(2) . ? C6 C7 1.404(2) . ? C6 H6 0.9400 . ? C10G C8G 1.405(2) . ? C10G C9G 1.413(2) . ? C8 C7 1.366(2) . ? C8 H8 0.9400 . ? C9G C4G 1.413(2) . ? C9G C5G 1.413(2) . ? C3 C4 1.368(2) . ? C3 C2 1.415(2) . ? C3 H3 0.9400 . ? C2 O1 1.3585(19) . ? C7 H7 0.9400 . ? C5 H5 0.9400 . ? C4 H4 0.9400 . ? C2G C3G 1.407(3) . ? C2G C11G 1.501(2) . ? C4G C3G 1.356(2) . ? C4G H4G 0.9400 . ? C3G H3G 0.9400 . ? C5G C6G 1.359(3) . ? C5G H5G 0.9400 . ? C8G C7G 1.367(3) . ? C8G H8G 0.9400 . ? C7G C6G 1.398(3) . ? C7G H7G 0.9400 . ? C6G H6G 0.9400 . ? O1 H1 0.974(7) . ? C11G H11A 0.9700 . ? C11G H11B 0.9700 . ? C11G H11C 0.9700 . ? 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 C2 C1 C10 119.09(13) . . ? C2 C1 C1 119.99(12) . 2_557 ? C10 C1 C1 120.92(12) . 2_557 ? C4 C9 C5 122.93(14) . . ? C4 C9 C10 118.36(14) . . ? C5 C9 C10 118.71(14) . . ? C8 C10 C1 122.08(13) . . ? C8 C10 C9 117.69(13) . . ? C1 C10 C9 120.23(13) . . ? C2G N1G C10G 118.76(14) . . ? C5 C6 C7 119.26(15) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N1G C10G C8G 118.62(14) . . ? N1G C10G C9G 122.12(14) . . ? C8G C10G C9G 119.25(14) . . ? C7 C8 C10 121.67(15) . . ? C7 C8 H8 119.2 . . ? C10 C8 H8 119.2 . . ? C4G C9G C5G 124.08(15) . . ? C4G C9G C10G 117.21(14) . . ? C5G C9G C10G 118.70(16) . . ? C4 C3 C2 120.60(15) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? O1 C2 C1 118.73(13) . . ? O1 C2 C3 120.65(13) . . ? C1 C2 C3 120.60(14) . . ? C8 C7 C6 120.71(16) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C6 C5 C9 121.94(15) . . ? C6 C5 H5 119.0 . . ? C9 C5 H5 119.0 . . ? C3 C4 C9 121.11(15) . . ? C3 C4 H4 119.4 . . ? C9 C4 H4 119.4 . . ? N1G C2G C3G 121.94(15) . . ? N1G C2G C11G 117.35(16) . . ? C3G C2G C11G 120.71(17) . . ? C3G C4G C9G 119.83(15) . . ? C3G C4G H4G 120.1 . . ? C9G C4G H4G 120.1 . . ? C4G C3G C2G 120.12(16) . . ? C4G C3G H3G 119.9 . . ? C2G C3G H3G 119.9 . . ? C6G C5G C9G 120.86(17) . . ? C6G C5G H5G 119.6 . . ? C9G C5G H5G 119.6 . . ? C7G C8G C10G 120.35(17) . . ? C7G C8G H8G 119.8 . . ? C10G C8G H8G 119.8 . . ? C8G C7G C6G 120.66(18) . . ? C8G C7G H7G 119.7 . . ? C6G C7G H7G 119.7 . . ? C5G C6G C7G 120.18(17) . . ? C5G C6G H6G 119.9 . . ? C7G C6G H6G 119.9 . . ? C2 O1 H1 110.6(12) . . ? C2G C11G H11A 109.5 . . ? C2G C11G H11B 109.5 . . ? H11A C11G H11B 109.5 . . ? C2G C11G H11C 109.5 . . ? H11A C11G H11C 109.5 . . ? H11B C11G H11C 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 C2 C1 C10 C8 -179.43(14) . . . . ? C1 C1 C10 C8 0.9(2) 2_557 . . . ? C2 C1 C10 C9 0.43(19) . . . . ? C1 C1 C10 C9 -179.24(14) 2_557 . . . ? C4 C9 C10 C8 -179.95(14) . . . . ? C5 C9 C10 C8 -0.07(19) . . . . ? C4 C9 C10 C1 0.2(2) . . . . ? C5 C9 C10 C1 -179.94(13) . . . . ? C2G N1G C10G C8G 178.43(15) . . . . ? C2G N1G C10G C9G -1.4(2) . . . . ? C1 C10 C8 C7 178.49(14) . . . . ? C9 C10 C8 C7 -1.4(2) . . . . ? N1G C10G C9G C4G 1.0(2) . . . . ? C8G C10G C9G C4G -178.86(14) . . . . ? N1G C10G C9G C5G -179.68(14) . . . . ? C8G C10G C9G C5G 0.5(2) . . . . ? C10 C1 C2 O1 178.12(13) . . . . ? C1 C1 C2 O1 -2.2(2) 2_557 . . . ? C10 C1 C2 C3 -0.7(2) . . . . ? C1 C1 C2 C3 179.00(14) 2_557 . . . ? C4 C3 C2 O1 -178.48(15) . . . . ? C4 C3 C2 C1 0.3(2) . . . . ? C10 C8 C7 C6 1.7(2) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? C7 C6 C5 C9 -0.8(2) . . . . ? C4 C9 C5 C6 -178.96(15) . . . . ? C10 C9 C5 C6 1.2(2) . . . . ? C2 C3 C4 C9 0.4(2) . . . . ? C5 C9 C4 C3 179.55(15) . . . . ? C10 C9 C4 C3 -0.6(2) . . . . ? C10G N1G C2G C3G 0.6(2) . . . . ? C10G N1G C2G C11G -178.55(14) . . . . ? C5G C9G C4G C3G -178.98(15) . . . . ? C10G C9G C4G C3G 0.3(2) . . . . ? C9G C4G C3G C2G -1.1(2) . . . . ? N1G C2G C3G C4G 0.7(3) . . . . ? C11G C2G C3G C4G 179.80(15) . . . . ? C4G C9G C5G C6G 179.49(16) . . . . ? C10G C9G C5G C6G 0.2(2) . . . . ? N1G C10G C8G C7G 179.33(15) . . . . ? C9G C10G C8G C7G -0.8(2) . . . . ? C10G C8G C7G C6G 0.5(3) . . . . ? C9G C5G C6G C7G -0.5(3) . . . . ? C8G C7G C6G C5G 0.2(3) . . . . ? 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 N1G 0.974(14) 1.784(13) 2.7390(17) 166.2(15) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.130 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.034 #===END data_c_BINAP.2.5(6MeQ) _database_code_depnum_ccdc_archive 'CCDC 224352' _chemical_name_common '2,2’-dihydroxyl-1,1’-binaphthyl 6-methylquinoline clathrate' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2’-dihydroxyl-1,1’-binaphthyl 6-methylquinoline clathrate ; _chemical_melting_point ? _chemical_formula_moiety C20H14O22.5C10H9N1 _chemical_formula_sum 'C45 H36.50 N2.50 O2' _chemical_formula_weight 644.27 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' N N 0.0061 0.0033 '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 8.83960(10) _cell_length_b 9.46950(10) _cell_length_c 21.6106(3) _cell_angle_alpha 94.6520(10) _cell_angle_beta 98.0680(10) _cell_angle_gamma 103.8220(10) _cell_volume 1726.77(4) _cell_formula_units_Z 2 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9970 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 32mm; combination of \f and \w scans of 1.0\%, 30s per \%, 2 iterations. ; _diffrn_ambient_temperature 203(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 '1.0\% \f scans and \w scans' _diffrn_reflns_number 14800 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7905 _reflns_number_gt 4984 _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-86 (Sheldrick, 1986)' _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^)+(0.0955P)^2^+1.5288P] 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 7905 _refine_ls_number_parameters 429 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.2283 _refine_ls_wR_factor_gt 0.2028 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.014 _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 0.6636(2) 0.2596(2) 0.26556(9) 0.0413(5) Uani 1 1 d D . . C4C C 0.5347(6) 0.0507(5) 0.4094(2) 0.0870(13) Uiso 1 1 d . . . O2 O 0.5088(2) 0.2359(2) 0.12202(9) 0.0394(5) Uani 1 1 d D . . C2C C 0.7738(9) -0.0413(8) 0.4191(3) 0.134(2) Uiso 1 1 d . . . C11 C 0.4683(3) 0.0324(3) 0.17981(11) 0.0264(5) Uani 1 1 d . . . C1 C 0.4046(3) 0.1189(3) 0.22622(11) 0.0268(5) Uani 1 1 d . . . C20 C 0.4778(3) -0.1137(3) 0.18681(11) 0.0278(5) Uani 1 1 d . . . C10 C 0.2387(3) 0.0885(3) 0.22738(11) 0.0264(5) Uani 1 1 d . . . C9 C 0.1804(3) 0.1784(3) 0.26951(12) 0.0307(5) Uani 1 1 d . . . N1B N 0.7871(3) 0.3984(3) 0.10118(11) 0.0412(6) Uani 1 1 d D . . C6C C 0.6200(6) -0.0441(5) 0.5045(2) 0.0853(13) Uiso 1 1 d . . . C3 C 0.4466(3) 0.3222(3) 0.30792(12) 0.0347(6) Uani 1 1 d . . . H3 H 0.5169 0.4004 0.3349 0.042 Uiso 1 1 calc R . . C2 C 0.5054(3) 0.2337(3) 0.26643(12) 0.0296(5) Uani 1 1 d . . . C19 C 0.5387(3) -0.1919(3) 0.14119(12) 0.0324(6) Uani 1 1 d . . . N1A N 0.8772(3) 0.5081(3) 0.32917(11) 0.0429(6) Uiso 1 1 d D . . C3C C 0.6443(11) 0.0231(10) 0.3869(4) 0.080(2) Uiso 0.50 1 d P . . C8 C 0.1285(3) -0.0263(3) 0.18681(12) 0.0306(5) Uani 1 1 d . . . H8 H 0.1651 -0.0864 0.1587 0.037 Uiso 1 1 calc R . . C9B C 0.9771(3) 0.6038(3) 0.07235(12) 0.0320(6) Uani 1 1 d . . . C7 C -0.0300(3) -0.0520(3) 0.18748(13) 0.0372(6) Uani 1 1 d . . . H7 H -0.1007 -0.1296 0.1603 0.045 Uiso 1 1 calc R . . C12 C 0.5207(3) 0.0968(3) 0.12904(12) 0.0313(6) Uani 1 1 d . . . C10B C 0.8275(3) 0.5027(3) 0.06207(12) 0.0334(6) Uani 1 1 d . . . C13 C 0.5824(3) 0.0192(3) 0.08418(12) 0.0379(6) Uani 1 1 d . . . H13 H 0.6182 0.0648 0.0500 0.045 Uiso 1 1 calc R . . C5 C 0.0146(3) 0.1486(3) 0.26839(13) 0.0407(7) Uani 1 1 d . . . H5 H -0.0251 0.2075 0.2958 0.049 Uiso 1 1 calc R . . C18 C 0.4305(3) -0.1855(3) 0.23904(12) 0.0340(6) Uani 1 1 d . . . H18 H 0.3903 -0.1363 0.2699 0.041 Uiso 1 1 calc R . . C14 C 0.5903(3) -0.1206(3) 0.09001(13) 0.0394(6) Uani 1 1 d . . . H14 H 0.6307 -0.1709 0.0596 0.047 Uiso 1 1 calc R . . C15 C 0.5484(3) -0.3367(3) 0.14918(14) 0.0423(7) Uani 1 1 d . . . H15 H 0.5890 -0.3881 0.1192 0.051 Uiso 1 1 calc R . . C4 C 0.2882(3) 0.2950(3) 0.30907(13) 0.0365(6) Uani 1 1 d . . . H4 H 0.2508 0.3552 0.3368 0.044 Uiso 1 1 calc R . . C5B C 1.0084(3) 0.7120(3) 0.03128(13) 0.0395(6) Uani 1 1 d . . . H5B H 1.1082 0.7791 0.0378 0.047 Uiso 1 1 calc R . . C10A C 0.9884(3) 0.4971(3) 0.37854(12) 0.0350(6) Uiso 1 1 d . . . C9A C 1.1292(3) 0.6084(3) 0.39891(13) 0.0384(6) Uani 1 1 d . . . C17 C 0.4430(3) -0.3254(3) 0.24466(14) 0.0419(7) Uani 1 1 d . . . H17 H 0.4123 -0.3704 0.2797 0.050 Uiso 1 1 calc R . . C8B C 0.7148(3) 0.5100(3) 0.01010(13) 0.0396(6) Uani 1 1 d . . . H8B H 0.6160 0.4414 0.0019 0.048 Uiso 1 1 calc R . . C16 C 0.5007(4) -0.4031(3) 0.19915(15) 0.0458(7) Uani 1 1 d . . . H16 H 0.5062 -0.4999 0.2032 0.055 Uiso 1 1 calc R . . C4B C 1.0884(3) 0.5903(3) 0.12412(13) 0.0402(6) Uani 1 1 d . . . H4B H 1.1905 0.6535 0.1321 0.048 Uiso 1 1 calc R . . C6 C -0.0882(3) 0.0372(3) 0.22877(14) 0.0431(7) Uani 1 1 d . . . H6 H -0.1974 0.0198 0.2289 0.052 Uiso 1 1 calc R . . C6B C 0.8964(4) 0.7211(3) -0.01789(13) 0.0413(7) Uani 1 1 d . . . C7B C 0.7492(4) 0.6169(3) -0.02835(14) 0.0436(7) Uani 1 1 d . . . H7B H 0.6728 0.6210 -0.0626 0.052 Uiso 1 1 calc R . . C7A C 1.0698(4) 0.3573(4) 0.45904(15) 0.0477(7) Uani 1 1 d . . . H7A H 1.0495 0.2723 0.4794 0.057 Uiso 1 1 calc R . . C8A C 0.9613(4) 0.3717(3) 0.41010(14) 0.0444(7) Uani 1 1 d . . . H8A H 0.8677 0.2972 0.3974 0.053 Uiso 1 1 calc R . . C5A C 1.2384(3) 0.5888(4) 0.44977(14) 0.0461(7) Uani 1 1 d . . . H5A H 1.3325 0.6623 0.4632 0.055 Uiso 1 1 calc R . . C6A C 1.2115(4) 0.4662(4) 0.48001(13) 0.0453(7) Uani 1 1 d . . . C3B C 1.0461(4) 0.4851(3) 0.16212(14) 0.0469(7) Uani 1 1 d . . . H3B H 1.1187 0.4747 0.1966 0.056 Uiso 1 1 calc R . . C2B C 0.8937(4) 0.3926(3) 0.14940(15) 0.0471(7) Uani 1 1 d . . . H2B H 0.8656 0.3222 0.1768 0.057 Uiso 1 1 calc R . . C2A C 0.9051(4) 0.6283(4) 0.30121(15) 0.0527(8) Uani 1 1 d . . . H2A H 0.8293 0.6367 0.2675 0.063 Uiso 1 1 calc R . . C11A C 1.3268(4) 0.4482(5) 0.53553(16) 0.0654(10) Uani 1 1 d . . . HA1 H 1.4088 0.5386 0.5477 0.098 Uiso 1 1 calc R . . HA2 H 1.3742 0.3695 0.5240 0.098 Uiso 1 1 calc R . . HA3 H 1.2715 0.4248 0.5706 0.098 Uiso 1 1 calc R . . C4A C 1.1525(4) 0.7334(4) 0.36688(16) 0.0546(8) Uani 1 1 d . . . H4A H 1.2451 0.8094 0.3788 0.065 Uiso 1 1 calc R . . C5C C 0.4932(10) 0.0194(9) 0.4717(4) 0.071(2) Uiso 0.50 1 d P . . C3A C 1.0407(4) 0.7440(4) 0.31865(17) 0.0611(9) Uani 1 1 d . . . H3A H 1.0542 0.8277 0.2974 0.073 Uiso 1 1 calc R . . C11B C 0.9265(5) 0.8380(4) -0.06157(17) 0.0643(10) Uani 1 1 d . . . HB1 H 0.8609 0.9050 -0.0554 0.096 Uiso 1 1 calc R . . HB2 H 0.9012 0.7924 -0.1049 0.096 Uiso 1 1 calc R . . HB3 H 1.0369 0.8915 -0.0525 0.096 Uiso 1 1 calc R . . N1C N 0.7312(11) -0.0649(10) 0.4851(4) 0.103(3) Uiso 0.50 1 d P . . C7C C 0.6575(13) -0.0107(12) 0.4420(5) 0.099(3) Uiso 0.50 1 d P . . C8C C 0.4310(12) 0.0771(11) 0.4290(5) 0.086(3) Uiso 0.50 1 d P . . H2 H 0.605(2) 0.289(4) 0.1090(17) 0.086(13) Uiso 1 1 d D . . H1 H 0.721(3) 0.350(3) 0.2916(16) 0.084(13) 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 0.0235(9) 0.0423(11) 0.0516(12) -0.0086(9) 0.0023(8) 0.0026(8) O2 0.0368(11) 0.0361(11) 0.0497(11) 0.0160(9) 0.0127(9) 0.0108(8) C11 0.0190(11) 0.0289(12) 0.0291(12) 0.0001(10) 0.0014(9) 0.0044(9) C1 0.0266(12) 0.0259(12) 0.0287(12) 0.0046(10) 0.0040(9) 0.0079(10) C20 0.0205(11) 0.0277(12) 0.0327(13) -0.0003(10) 0.0010(9) 0.0047(9) C10 0.0247(12) 0.0277(12) 0.0286(12) 0.0067(10) 0.0045(9) 0.0091(10) C9 0.0296(13) 0.0320(13) 0.0341(13) 0.0068(11) 0.0080(10) 0.0120(11) N1B 0.0368(13) 0.0403(13) 0.0471(14) 0.0125(11) 0.0102(11) 0.0067(10) C3 0.0367(14) 0.0288(13) 0.0339(14) -0.0037(11) -0.0011(11) 0.0058(11) C2 0.0242(12) 0.0294(13) 0.0341(13) 0.0052(10) 0.0031(10) 0.0053(10) C19 0.0228(12) 0.0345(14) 0.0368(14) -0.0036(11) 0.0007(10) 0.0062(10) C8 0.0266(12) 0.0331(13) 0.0327(13) 0.0034(11) 0.0046(10) 0.0086(10) C9B 0.0331(13) 0.0278(13) 0.0362(14) 0.0021(11) 0.0081(11) 0.0089(11) C7 0.0254(13) 0.0387(15) 0.0441(15) 0.0048(12) 0.0003(11) 0.0047(11) C12 0.0246(12) 0.0334(14) 0.0341(13) 0.0040(11) 0.0017(10) 0.0055(10) C10B 0.0319(14) 0.0329(14) 0.0380(14) 0.0032(11) 0.0097(11) 0.0114(11) C13 0.0340(14) 0.0459(16) 0.0314(14) 0.0028(12) 0.0089(11) 0.0039(12) C5 0.0358(15) 0.0490(17) 0.0432(16) 0.0046(13) 0.0124(12) 0.0191(13) C18 0.0310(13) 0.0334(14) 0.0371(14) 0.0055(11) 0.0036(11) 0.0076(11) C14 0.0345(14) 0.0479(17) 0.0351(14) -0.0050(12) 0.0083(11) 0.0111(12) C15 0.0352(15) 0.0381(16) 0.0534(18) -0.0065(13) 0.0022(13) 0.0161(12) C4 0.0392(15) 0.0365(15) 0.0366(14) -0.0022(11) 0.0084(11) 0.0157(12) C5B 0.0430(16) 0.0303(14) 0.0448(16) 0.0018(12) 0.0132(13) 0.0058(12) C9A 0.0343(14) 0.0384(15) 0.0378(15) -0.0017(12) 0.0038(11) 0.0033(12) C17 0.0440(16) 0.0359(15) 0.0453(16) 0.0105(12) 0.0007(13) 0.0114(13) C8B 0.0288(14) 0.0449(16) 0.0455(16) 0.0040(13) 0.0053(12) 0.0113(12) C16 0.0455(17) 0.0299(14) 0.0609(19) 0.0030(14) -0.0018(14) 0.0144(13) C4B 0.0349(14) 0.0372(15) 0.0451(16) -0.0005(12) 0.0020(12) 0.0067(12) C6 0.0244(13) 0.0519(18) 0.0538(18) 0.0073(14) 0.0071(12) 0.0104(12) C6B 0.0558(18) 0.0330(15) 0.0400(15) 0.0056(12) 0.0117(13) 0.0183(13) C7B 0.0455(17) 0.0495(18) 0.0395(15) 0.0039(13) 0.0024(13) 0.0226(14) C7A 0.0546(19) 0.0449(17) 0.0488(17) 0.0089(14) 0.0170(15) 0.0168(15) C8A 0.0399(16) 0.0389(16) 0.0501(17) -0.0013(13) 0.0098(13) 0.0025(13) C5A 0.0359(15) 0.0542(19) 0.0423(16) -0.0050(14) 0.0022(12) 0.0061(13) C6A 0.0469(17) 0.059(2) 0.0344(15) 0.0011(14) 0.0082(13) 0.0223(15) C3B 0.0464(17) 0.0496(18) 0.0426(16) 0.0090(14) -0.0013(13) 0.0121(14) C2B 0.0503(18) 0.0455(17) 0.0483(17) 0.0184(14) 0.0117(14) 0.0111(14) C2A 0.0472(18) 0.062(2) 0.0446(17) 0.0070(15) -0.0026(14) 0.0115(16) C11A 0.064(2) 0.096(3) 0.0451(19) 0.0122(19) 0.0067(16) 0.037(2) C4A 0.0488(19) 0.0463(18) 0.058(2) 0.0078(15) 0.0026(15) -0.0059(15) C3A 0.065(2) 0.052(2) 0.059(2) 0.0199(17) 0.0024(17) 0.0013(17) C11B 0.095(3) 0.047(2) 0.057(2) 0.0194(16) 0.0173(19) 0.0224(19) _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 C2 1.364(3) . ? O1 H1 0.968(9) . ? C4C C8C 1.133(10) . ? C4C C3C 1.216(10) . ? C4C C7C 1.471(12) . ? C4C C5C 1.478(9) . ? O2 C12 1.365(3) . ? O2 H2 0.969(8) . ? C2C C7C 1.284(12) . ? C2C C3C 1.531(11) . ? C2C N1C 1.546(11) . ? C11 C12 1.381(3) . ? C11 C20 1.424(3) . ? C11 C1 1.497(3) . ? C1 C2 1.377(3) . ? C1 C10 1.430(3) . ? C20 C19 1.425(3) . ? C20 C18 1.426(4) . ? C10 C8 1.414(3) . ? C10 C9 1.426(3) . ? C9 C4 1.405(4) . ? C9 C5 1.421(4) . ? N1B C2B 1.317(4) . ? N1B C10B 1.367(3) . ? C6C N1C 1.173(9) . ? C6C C5C 1.248(9) 2_656 ? C6C C7C 1.476(12) . ? C6C C5C 1.514(10) . ? C6C C8C 1.598(11) 2_656 ? C3 C4 1.365(4) . ? C3 C2 1.412(4) . ? C3 H3 0.9400 . ? C19 C14 1.415(4) . ? C19 C15 1.417(4) . ? N1A C2A 1.319(4) . ? N1A C10A 1.374(4) . ? C3C C7C 1.255(13) . ? C8 C7 1.366(3) . ? C8 H8 0.9400 . ? C9B C10B 1.412(4) . ? C9B C5B 1.413(4) . ? C9B C4B 1.418(4) . ? C7 C6 1.410(4) . ? C7 H7 0.9400 . ? C12 C13 1.415(4) . ? C10B C8B 1.411(4) . ? C13 C14 1.357(4) . ? C13 H13 0.9400 . ? C5 C6 1.359(4) . ? C5 H5 0.9400 . ? C18 C17 1.370(4) . ? C18 H18 0.9400 . ? C14 H14 0.9400 . ? C15 C16 1.361(4) . ? C15 H15 0.9400 . ? C4 H4 0.9400 . ? C5B C6B 1.371(4) . ? C5B H5B 0.9400 . ? C10A C8A 1.405(4) . ? C10A C9A 1.414(4) . ? C9A C4A 1.407(4) . ? C9A C5A 1.413(4) . ? C17 C16 1.404(4) . ? C17 H17 0.9400 . ? C8B C7B 1.367(4) . ? C8B H8B 0.9400 . ? C16 H16 0.9400 . ? C4B C3B 1.359(4) . ? C4B H4B 0.9400 . ? C6 H6 0.9400 . ? C6B C7B 1.408(4) . ? C6B C11B 1.512(4) . ? C7B H7B 0.9400 . ? C7A C8A 1.363(4) . ? C7A C6A 1.409(5) . ? C7A H7A 0.9400 . ? C8A H8A 0.9400 . ? C5A C6A 1.365(4) . ? C5A H5A 0.9400 . ? C6A C11A 1.510(4) . ? C3B C2B 1.397(4) . ? C3B H3B 0.9400 . ? C2B H2B 0.9400 . ? C2A C3A 1.399(5) . ? C2A H2A 0.9400 . ? C11A HA1 0.9700 . ? C11A HA2 0.9700 . ? C11A HA3 0.9700 . ? C4A C3A 1.360(5) . ? C4A H4A 0.9400 . ? C5C C8C 1.239(12) . ? C5C C6C 1.248(9) 2_656 ? C5C C5C 1.304(16) 2_656 ? C5C C7C 1.741(14) . ? C3A H3A 0.9400 . ? C11B HB1 0.9700 . ? C11B HB2 0.9700 . ? C11B HB3 0.9700 . ? N1C C7C 1.274(13) . ? C8C C6C 1.598(11) 2_656 ? 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 C2 O1 H1 111.3(19) . . ? C8C C4C C3C 178.3(9) . . ? C8C C4C C7C 127.0(8) . . ? C3C C4C C7C 54.7(6) . . ? C8C C4C C5C 54.7(6) . . ? C3C C4C C5C 126.9(7) . . ? C7C C4C C5C 72.3(6) . . ? C12 O2 H2 108(2) . . ? C7C C2C C3C 52.1(6) . . ? C7C C2C N1C 52.5(6) . . ? C3C C2C N1C 104.6(7) . . ? C12 C11 C20 119.1(2) . . ? C12 C11 C1 118.9(2) . . ? C20 C11 C1 122.0(2) . . ? C2 C1 C10 119.2(2) . . ? C2 C1 C11 120.0(2) . . ? C10 C1 C11 120.7(2) . . ? C11 C20 C19 119.9(2) . . ? C11 C20 C18 122.2(2) . . ? C19 C20 C18 117.9(2) . . ? C8 C10 C9 118.3(2) . . ? C8 C10 C1 122.2(2) . . ? C9 C10 C1 119.5(2) . . ? C4 C9 C5 122.6(2) . . ? C4 C9 C10 118.9(2) . . ? C5 C9 C10 118.4(2) . . ? C2B N1B C10B 117.9(2) . . ? N1C C6C C5C 176.6(8) . 2_656 ? N1C C6C C7C 56.1(6) . . ? C5C C6C C7C 126.5(7) 2_656 . ? N1C C6C C5C 127.3(7) . . ? C5C C6C C5C 55.4(6) 2_656 . ? C7C C6C C5C 71.2(6) . . ? N1C C6C C8C 127.7(7) . 2_656 ? C5C C6C C8C 49.8(5) 2_656 2_656 ? C7C C6C C8C 176.2(7) . 2_656 ? C5C C6C C8C 105.1(6) . 2_656 ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? O1 C2 C1 118.5(2) . . ? O1 C2 C3 120.6(2) . . ? C1 C2 C3 120.8(2) . . ? C14 C19 C15 122.3(2) . . ? C14 C19 C20 118.5(2) . . ? C15 C19 C20 119.1(2) . . ? C2A N1A C10A 117.6(3) . . ? C4C C3C C7C 73.1(8) . . ? C4C C3C C2C 126.9(8) . . ? C7C C3C C2C 53.8(6) . . ? C7 C8 C10 121.5(2) . . ? C7 C8 H8 119.2 . . ? C10 C8 H8 119.2 . . ? C10B C9B C5B 119.1(2) . . ? C10B C9B C4B 117.3(2) . . ? C5B C9B C4B 123.6(3) . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O2 C12 C11 118.8(2) . . ? O2 C12 C13 120.4(2) . . ? C11 C12 C13 120.8(2) . . ? N1B C10B C8B 118.6(2) . . ? N1B C10B C9B 122.3(2) . . ? C8B C10B C9B 119.1(2) . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C6 C5 C9 121.8(3) . . ? C6 C5 H5 119.1 . . ? C9 C5 H5 119.1 . . ? C17 C18 C20 120.6(3) . . ? C17 C18 H18 119.7 . . ? C20 C18 H18 119.7 . . ? C13 C14 C19 121.1(2) . . ? C13 C14 H14 119.5 . . ? C19 C14 H14 119.5 . . ? C16 C15 C19 121.7(3) . . ? C16 C15 H15 119.2 . . ? C19 C15 H15 119.2 . . ? C3 C4 C9 121.0(2) . . ? C3 C4 H4 119.5 . . ? C9 C4 H4 119.5 . . ? C6B C5B C9B 121.3(3) . . ? C6B C5B H5B 119.3 . . ? C9B C5B H5B 119.3 . . ? N1A C10A C8A 119.1(3) . . ? N1A C10A C9A 122.1(2) . . ? C8A C10A C9A 118.8(3) . . ? C4A C9A C5A 123.6(3) . . ? C4A C9A C10A 117.6(3) . . ? C5A C9A C10A 118.8(3) . . ? C18 C17 C16 121.4(3) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C7B C8B C10B 120.0(3) . . ? C7B C8B H8B 120.0 . . ? C10B C8B H8B 120.0 . . ? C15 C16 C17 119.3(3) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C3B C4B C9B 119.4(3) . . ? C3B C4B H4B 120.3 . . ? C9B C4B H4B 120.3 . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C5B C6B C7B 118.7(3) . . ? C5B C6B C11B 122.1(3) . . ? C7B C6B C11B 119.2(3) . . ? C8B C7B C6B 121.7(3) . . ? C8B C7B H7B 119.2 . . ? C6B C7B H7B 119.2 . . ? C8A C7A C6A 121.9(3) . . ? C8A C7A H7A 119.1 . . ? C6A C7A H7A 119.1 . . ? C7A C8A C10A 120.5(3) . . ? C7A C8A H8A 119.8 . . ? C10A C8A H8A 119.8 . . ? C6A C5A C9A 122.0(3) . . ? C6A C5A H5A 119.0 . . ? C9A C5A H5A 119.0 . . ? C5A C6A C7A 118.0(3) . . ? C5A C6A C11A 121.6(3) . . ? C7A C6A C11A 120.3(3) . . ? C4B C3B C2B 119.3(3) . . ? C4B C3B H3B 120.4 . . ? C2B C3B H3B 120.4 . . ? N1B C2B C3B 123.7(3) . . ? N1B C2B H2B 118.1 . . ? C3B C2B H2B 118.1 . . ? N1A C2A C3A 124.0(3) . . ? N1A C2A H2A 118.0 . . ? C3A C2A H2A 118.0 . . ? C6A C11A HA1 109.5 . . ? C6A C11A HA2 109.5 . . ? HA1 C11A HA2 109.5 . . ? C6A C11A HA3 109.5 . . ? HA1 C11A HA3 109.5 . . ? HA2 C11A HA3 109.5 . . ? C3A C4A C9A 119.8(3) . . ? C3A C4A H4A 120.1 . . ? C9A C4A H4A 120.1 . . ? C8C C5C C6C 80.0(7) . 2_656 ? C8C C5C C5C 152.4(12) . 2_656 ? C6C C5C C5C 72.7(7) 2_656 2_656 ? C8C C5C C4C 48.3(5) . . ? C6C C5C C4C 128.3(7) 2_656 . ? C5C C5C C4C 158.9(11) 2_656 . ? C8C C5C C6C 155.2(9) . . ? C6C C5C C6C 124.6(6) 2_656 . ? C5C C5C C6C 51.9(6) 2_656 . ? C4C C5C C6C 107.1(6) . . ? C8C C5C C7C 101.9(8) . . ? C6C C5C C7C 177.1(8) 2_656 . ? C5C C5C C7C 105.3(9) 2_656 . ? C4C C5C C7C 53.6(5) . . ? C6C C5C C7C 53.4(5) . . ? C4A C3A C2A 118.9(3) . . ? C4A C3A H3A 120.5 . . ? C2A C3A H3A 120.5 . . ? C6B C11B HB1 109.5 . . ? C6B C11B HB2 109.5 . . ? HB1 C11B HB2 109.5 . . ? C6B C11B HB3 109.5 . . ? HB1 C11B HB3 109.5 . . ? HB2 C11B HB3 109.5 . . ? C6C N1C C7C 74.1(8) . . ? C6C N1C C2C 127.1(8) . . ? C7C N1C C2C 53.1(6) . . ? C3C C7C N1C 148.5(12) . . ? C3C C7C C2C 74.1(8) . . ? N1C C7C C2C 74.4(8) . . ? C3C C7C C4C 52.2(6) . . ? N1C C7C C4C 159.2(11) . . ? C2C C7C C4C 126.4(10) . . ? C3C C7C C6C 161.2(11) . . ? N1C C7C C6C 49.8(6) . . ? C2C C7C C6C 124.1(9) . . ? C4C C7C C6C 109.4(8) . . ? C3C C7C C5C 106.1(9) . . ? N1C C7C C5C 105.2(9) . . ? C2C C7C C5C 176.4(10) . . ? C4C C7C C5C 54.0(5) . . ? C6C C7C C5C 55.4(5) . . ? C4C C8C C5C 77.0(8) . . ? C4C C8C C6C 127.2(8) . 2_656 ? C5C C8C C6C 50.3(6) . 2_656 ? 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 C11 C1 C2 -71.2(3) . . . . ? C20 C11 C1 C2 108.2(3) . . . . ? C12 C11 C1 C10 105.8(3) . . . . ? C20 C11 C1 C10 -74.9(3) . . . . ? C12 C11 C20 C19 -0.9(3) . . . . ? C1 C11 C20 C19 179.7(2) . . . . ? C12 C11 C20 C18 178.1(2) . . . . ? C1 C11 C20 C18 -1.3(3) . . . . ? C2 C1 C10 C8 179.1(2) . . . . ? C11 C1 C10 C8 2.2(4) . . . . ? C2 C1 C10 C9 0.7(3) . . . . ? C11 C1 C10 C9 -176.2(2) . . . . ? C8 C10 C9 C4 -178.5(2) . . . . ? C1 C10 C9 C4 -0.1(3) . . . . ? C8 C10 C9 C5 -0.3(3) . . . . ? C1 C10 C9 C5 178.1(2) . . . . ? C10 C1 C2 O1 178.8(2) . . . . ? C11 C1 C2 O1 -4.2(3) . . . . ? C10 C1 C2 C3 -0.9(4) . . . . ? C11 C1 C2 C3 176.1(2) . . . . ? C4 C3 C2 O1 -179.3(2) . . . . ? C4 C3 C2 C1 0.3(4) . . . . ? C11 C20 C19 C14 0.8(3) . . . . ? C18 C20 C19 C14 -178.3(2) . . . . ? C11 C20 C19 C15 179.5(2) . . . . ? C18 C20 C19 C15 0.5(3) . . . . ? C8C C4C C3C C7C -172(30) . . . . ? C5C C4C C3C C7C -4.9(10) . . . . ? C8C C4C C3C C2C -172(30) . . . . ? C7C C4C C3C C2C 0.3(8) . . . . ? C5C C4C C3C C2C -4.6(14) . . . . ? C7C C2C C3C C4C -0.4(10) . . . . ? N1C C2C C3C C4C 1.0(12) . . . . ? N1C C2C C3C C7C 1.3(9) . . . . ? C9 C10 C8 C7 -0.1(4) . . . . ? C1 C10 C8 C7 -178.5(2) . . . . ? C10 C8 C7 C6 0.5(4) . . . . ? C20 C11 C12 O2 178.9(2) . . . . ? C1 C11 C12 O2 -1.7(3) . . . . ? C20 C11 C12 C13 0.3(4) . . . . ? C1 C11 C12 C13 179.7(2) . . . . ? C2B N1B C10B C8B 179.8(3) . . . . ? C2B N1B C10B C9B -0.9(4) . . . . ? C5B C9B C10B N1B -177.7(2) . . . . ? C4B C9B C10B N1B 2.3(4) . . . . ? C5B C9B C10B C8B 1.7(4) . . . . ? C4B C9B C10B C8B -178.4(2) . . . . ? O2 C12 C13 C14 -178.1(2) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C4 C9 C5 C6 178.5(3) . . . . ? C10 C9 C5 C6 0.4(4) . . . . ? C11 C20 C18 C17 -179.2(2) . . . . ? C19 C20 C18 C17 -0.2(4) . . . . ? C12 C13 C14 C19 -0.6(4) . . . . ? C15 C19 C14 C13 -178.7(3) . . . . ? C20 C19 C14 C13 0.0(4) . . . . ? C14 C19 C15 C16 179.0(3) . . . . ? C20 C19 C15 C16 0.3(4) . . . . ? C2 C3 C4 C9 0.4(4) . . . . ? C5 C9 C4 C3 -178.6(3) . . . . ? C10 C9 C4 C3 -0.5(4) . . . . ? C10B C9B C5B C6B 0.4(4) . . . . ? C4B C9B C5B C6B -179.5(3) . . . . ? C2A N1A C10A C8A 178.9(3) . . . . ? C2A N1A C10A C9A -0.7(4) . . . . ? N1A C10A C9A C4A 0.3(4) . . . . ? C8A C10A C9A C4A -179.3(3) . . . . ? N1A C10A C9A C5A -179.6(3) . . . . ? C8A C10A C9A C5A 0.7(4) . . . . ? C20 C18 C17 C16 -0.7(4) . . . . ? N1B C10B C8B C7B 177.3(2) . . . . ? C9B C10B C8B C7B -2.1(4) . . . . ? C19 C15 C16 C17 -1.2(4) . . . . ? C18 C17 C16 C15 1.5(4) . . . . ? C10B C9B C4B C3B -1.8(4) . . . . ? C5B C9B C4B C3B 178.2(3) . . . . ? C9 C5 C6 C7 0.1(4) . . . . ? C8 C7 C6 C5 -0.5(4) . . . . ? C9B C5B C6B C7B -2.0(4) . . . . ? C9B C5B C6B C11B 178.8(3) . . . . ? C10B C8B C7B C6B 0.5(4) . . . . ? C5B C6B C7B C8B 1.6(4) . . . . ? C11B C6B C7B C8B -179.2(3) . . . . ? C6A C7A C8A C10A 0.3(4) . . . . ? N1A C10A C8A C7A 179.7(3) . . . . ? C9A C10A C8A C7A -0.6(4) . . . . ? C4A C9A C5A C6A 179.6(3) . . . . ? C10A C9A C5A C6A -0.5(4) . . . . ? C9A C5A C6A C7A 0.1(4) . . . . ? C9A C5A C6A C11A -178.2(3) . . . . ? C8A C7A C6A C5A 0.0(4) . . . . ? C8A C7A C6A C11A 178.3(3) . . . . ? C9B C4B C3B C2B -0.1(4) . . . . ? C10B N1B C2B C3B -1.2(4) . . . . ? C4B C3B C2B N1B 1.7(5) . . . . ? C10A N1A C2A C3A 0.3(5) . . . . ? C5A C9A C4A C3A -179.5(3) . . . . ? C10A C9A C4A C3A 0.6(5) . . . . ? C3C C4C C5C C8C -179.6(11) . . . . ? C7C C4C C5C C8C 176.3(9) . . . . ? C8C C4C C5C C6C 0.9(9) . . . 2_656 ? C3C C4C C5C C6C -178.6(9) . . . 2_656 ? C7C C4C C5C C6C 177.2(10) . . . 2_656 ? C8C C4C C5C C5C -171(3) . . . 2_656 ? C3C C4C C5C C5C 9(3) . . . 2_656 ? C7C C4C C5C C5C 5(3) . . . 2_656 ? C8C C4C C5C C6C -176.5(10) . . . . ? C3C C4C C5C C6C 4.0(10) . . . . ? C7C C4C C5C C6C -0.2(6) . . . . ? C8C C4C C5C C7C -176.3(9) . . . . ? C3C C4C C5C C7C 4.2(9) . . . . ? N1C C6C C5C C8C -6(2) . . . . ? C5C C6C C5C C8C 171(3) 2_656 . . . ? C7C C6C C5C C8C -6(2) . . . . ? C8C C6C C5C C8C 174.2(18) 2_656 . . . ? N1C C6C C5C C6C -177.3(10) . . . 2_656 ? C5C C6C C5C C6C 0.000(1) 2_656 . . 2_656 ? C7C C6C C5C C6C -177.3(10) . . . 2_656 ? C8C C6C C5C C6C 3.0(9) 2_656 . . 2_656 ? N1C C6C C5C C5C -177.3(10) . . . 2_656 ? C7C C6C C5C C5C -177.3(10) . . . 2_656 ? C8C C6C C5C C5C 3.0(9) 2_656 . . 2_656 ? N1C C6C C5C C4C 0.2(11) . . . . ? C5C C6C C5C C4C 177.5(12) 2_656 . . . ? C7C C6C C5C C4C 0.2(6) . . . . ? C8C C6C C5C C4C -179.5(6) 2_656 . . . ? N1C C6C C5C C7C 0.0(9) . . . . ? C5C C6C C5C C7C 177.3(10) 2_656 . . . ? C8C C6C C5C C7C -179.8(7) 2_656 . . . ? C9A C4A C3A C2A -1.0(5) . . . . ? N1A C2A C3A C4A 0.6(6) . . . . ? C5C C6C N1C C7C -140(13) 2_656 . . . ? C5C C6C N1C C7C 0.0(10) . . . . ? C8C C6C N1C C7C 179.7(9) 2_656 . . . ? C5C C6C N1C C2C -144(13) 2_656 . . . ? C7C C6C N1C C2C -3.7(8) . . . . ? C5C C6C N1C C2C -3.7(14) . . . . ? C8C C6C N1C C2C 176.0(7) 2_656 . . . ? C7C C2C N1C C6C 4.5(10) . . . . ? C3C C2C N1C C6C 3.2(12) . . . . ? C3C C2C N1C C7C -1.3(9) . . . . ? C4C C3C C7C N1C 177(2) . . . . ? C2C C3C C7C N1C -3.0(19) . . . . ? C4C C3C C7C C2C 179.7(8) . . . . ? C2C C3C C7C C4C -179.7(8) . . . . ? C4C C3C C7C C6C 13(3) . . . . ? C2C C3C C7C C6C -167(4) . . . . ? C4C C3C C7C C5C 3.5(7) . . . . ? C2C C3C C7C C5C -176.2(10) . . . . ? C6C N1C C7C C3C -173(2) . . . . ? C2C N1C C7C C3C 3.0(19) . . . . ? C6C N1C C7C C2C -176.3(8) . . . . ? C6C N1C C7C C4C -1(3) . . . . ? C2C N1C C7C C4C 176(3) . . . . ? C2C N1C C7C C6C 176.3(8) . . . . ? C6C N1C C7C C5C 0.0(7) . . . . ? C2C N1C C7C C5C 176.3(10) . . . . ? N1C C2C C7C C3C -178.4(10) . . . . ? C3C C2C C7C N1C 178.4(10) . . . . ? C3C C2C C7C C4C 0.3(8) . . . . ? N1C C2C C7C C4C -178.1(15) . . . . ? C3C C2C C7C C6C 175.0(14) . . . . ? N1C C2C C7C C6C -3.4(8) . . . . ? C3C C2C C7C C5C 95(16) . . . . ? N1C C2C C7C C5C -84(16) . . . . ? C8C C4C C7C C3C 179.7(11) . . . . ? C5C C4C C7C C3C 175.9(9) . . . . ? C8C C4C C7C N1C 5(3) . . . . ? C3C C4C C7C N1C -175(3) . . . . ? C5C C4C C7C N1C 1(3) . . . . ? C8C C4C C7C C2C 179.4(10) . . . . ? C3C C4C C7C C2C -0.4(10) . . . . ? C5C C4C C7C C2C 175.5(12) . . . . ? C8C C4C C7C C6C 4.1(13) . . . . ? C3C C4C C7C C6C -175.7(11) . . . . ? C5C C4C C7C C6C 0.2(7) . . . . ? C8C C4C C7C C5C 3.8(10) . . . . ? C3C C4C C7C C5C -175.9(9) . . . . ? N1C C6C C7C C3C 169(4) . . . . ? C5C C6C C7C C3C -14(4) 2_656 . . . ? C5C C6C C7C C3C -11(3) . . . . ? C8C C6C C7C C3C -7(13) 2_656 . . . ? C5C C6C C7C N1C 177.2(10) 2_656 . . . ? C5C C6C C7C N1C -180.0(9) . . . . ? C8C C6C C7C N1C -176(10) 2_656 . . . ? N1C C6C C7C C2C 4.3(10) . . . . ? C5C C6C C7C C2C -178.4(9) 2_656 . . . ? C5C C6C C7C C2C -175.7(12) . . . . ? C8C C6C C7C C2C -172(10) 2_656 . . . ? N1C C6C C7C C4C 179.8(11) . . . . ? C5C C6C C7C C4C -3.0(12) 2_656 . . . ? C5C C6C C7C C4C -0.2(7) . . . . ? C8C C6C C7C C4C 3(11) 2_656 . . . ? N1C C6C C7C C5C 180.0(9) . . . . ? C5C C6C C7C C5C -2.8(10) 2_656 . . . ? C8C C6C C7C C5C 4(11) 2_656 . . . ? C8C C5C C7C C3C -6.2(11) . . . . ? C6C C5C C7C C3C -134(16) 2_656 . . . ? C5C C5C C7C C3C 178.6(11) 2_656 . . . ? C4C C5C C7C C3C -3.4(7) . . . . ? C6C C5C C7C C3C 176.4(11) . . . . ? C8C C5C C7C N1C 177.4(10) . . . . ? C6C C5C C7C N1C 49(16) 2_656 . . . ? C5C C5C C7C N1C 2.2(13) 2_656 . . . ? C4C C5C C7C N1C -179.7(11) . . . . ? C6C C5C C7C N1C 0.0(7) . . . . ? C8C C5C C7C C2C -100(16) . . . . ? C6C C5C C7C C2C 132(17) 2_656 . . . ? C5C C5C C7C C2C 85(16) 2_656 . . . ? C4C C5C C7C C2C -97(16) . . . . ? C6C C5C C7C C2C 83(16) . . . . ? C8C C5C C7C C4C -2.9(7) . . . . ? C6C C5C C7C C4C -131(16) 2_656 . . . ? C5C C5C C7C C4C -178.0(11) 2_656 . . . ? C6C C5C C7C C4C 179.8(8) . . . . ? C8C C5C C7C C6C 177.4(9) . . . . ? C6C C5C C7C C6C 49(16) 2_656 . . . ? C5C C5C C7C C6C 2.2(8) 2_656 . . . ? C4C C5C C7C C6C -179.8(8) . . . . ? C3C C4C C8C C5C 168(30) . . . . ? C7C C4C C8C C5C -4.5(11) . . . . ? C3C C4C C8C C6C 167(30) . . . 2_656 ? C7C C4C C8C C6C -5.2(15) . . . 2_656 ? C5C C4C C8C C6C -0.7(7) . . . 2_656 ? C6C C5C C8C C4C -179.3(7) 2_656 . . . ? C5C C5C C8C C4C 173(3) 2_656 . . . ? C6C C5C C8C C4C 8(2) . . . . ? C7C C5C C8C C4C 3.1(8) . . . . ? C5C C5C C8C C6C -8(2) 2_656 . . 2_656 ? C4C C5C C8C C6C 179.3(7) . . . 2_656 ? C6C C5C C8C C6C -173(2) . . . 2_656 ? C7C C5C C8C C6C -177.6(8) . . . 2_656 ? 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 N1A 0.97(3) 1.82(3) 2.760(3) 163(3) . O2 H2 N1B 0.97(3) 1.73(3) 2.690(3) 169(3) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.018 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.061 #===END data_c_BINAP.2(8MeQ) _database_code_depnum_ccdc_archive 'CCDC 224353' _chemical_name_common '2,2-dihydroxyl-1,1’-binaphthyl di-8-methylquinoline' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2-dihydroxyl-1,1’-binaphthyl di-8-methylquinoline ; _chemical_melting_point ? _chemical_formula_moiety C20H14O22C10H9N1 _chemical_formula_sum 'C40 H32 N2 O2' _chemical_formula_weight 572.68 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' N N 0.0061 0.0033 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.4495(3) _cell_length_b 11.0481(3) _cell_length_c 19.6571(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.1000(10) _cell_angle_gamma 90.00 _cell_volume 3029.70(14) _cell_formula_units_Z 4 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_min 0.9699 _exptl_absorpt_correction_T_max 0.9932 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 36mm; combination of \f and \w scans of 1.0\%, 50s per \%, 2 iterations. ; _diffrn_ambient_temperature 203(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 '1.0\% \f scans and \w scans' _diffrn_reflns_number 5783 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3402 _reflns_number_gt 1937 _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-86 (Sheldrick, 1986)' _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^)+(0.0637P)^2^+1.3132P] 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 3402 _refine_ls_number_parameters 204 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _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 C1 C 0.02806(12) 0.53714(15) 0.22273(9) 0.0334(4) Uani 1 1 d . . . C9 C 0.15659(13) 0.45283(16) 0.17484(10) 0.0394(4) Uani 1 1 d . . . C10 C 0.10369(12) 0.45221(15) 0.22671(9) 0.0342(4) Uani 1 1 d . . . C2 C 0.00692(12) 0.61851(16) 0.16791(10) 0.0390(4) Uani 1 1 d . . . C8 C 0.12858(13) 0.36455(17) 0.28075(10) 0.0426(5) Uani 1 1 d . . . H8 H 0.0948 0.3621 0.3156 0.051 Uiso 1 1 calc R . . C3 C 0.05872(15) 0.61758(18) 0.11575(11) 0.0495(5) Uani 1 1 d . . . H3 H 0.0428 0.6730 0.0782 0.059 Uiso 1 1 calc R . . C5 C 0.23164(14) 0.36743(19) 0.18020(12) 0.0502(5) Uani 1 1 d . . . H5 H 0.2673 0.3683 0.1464 0.060 Uiso 1 1 calc R . . C7 C 0.20085(14) 0.28319(19) 0.28336(11) 0.0522(5) Uani 1 1 d . . . H7 H 0.2155 0.2254 0.3197 0.063 Uiso 1 1 calc R . . C6 C 0.25296(15) 0.2850(2) 0.23278(12) 0.0566(6) Uani 1 1 d . . . H6 H 0.3027 0.2290 0.2352 0.068 Uiso 1 1 calc R . . C4 C 0.13105(15) 0.53747(18) 0.11944(11) 0.0502(5) Uani 1 1 d . . . H4 H 0.1647 0.5384 0.0845 0.060 Uiso 1 1 calc R . . C10G C -0.07741(13) 1.00041(16) 0.06149(10) 0.0402(5) Uani 1 1 d . . . C9G C -0.13748(14) 1.0769(2) 0.00954(11) 0.0488(5) Uani 1 1 d . . . N1G N -0.08652(13) 0.87660(16) 0.05610(10) 0.0545(5) Uani 1 1 d D . . C8G C -0.00664(15) 1.0520(2) 0.11715(11) 0.0530(5) Uani 1 1 d . . . C5G C -0.12504(16) 1.2037(2) 0.01624(13) 0.0567(6) Uani 1 1 d . . . H5G H -0.1650 1.2555 -0.0166 0.068 Uiso 1 1 calc R . . C4G C -0.20433(17) 1.0240(2) -0.04601(12) 0.0638(6) Uani 1 1 d . . . H4G H -0.2458 1.0728 -0.0798 0.077 Uiso 1 1 calc R . . C6G C -0.05612(19) 1.2504(2) 0.06952(14) 0.0651(7) Uani 1 1 d . . . H6G H -0.0473 1.3347 0.0730 0.078 Uiso 1 1 calc R . . C3G C -0.20992(19) 0.9009(3) -0.05166(13) 0.0744(7) Uani 1 1 d . . . H3G H -0.2536 0.8638 -0.0898 0.089 Uiso 1 1 calc R . . C7G C 0.00295(18) 1.1739(2) 0.12011(13) 0.0651(6) Uani 1 1 d . . . H7G H 0.0504 1.2087 0.1570 0.078 Uiso 1 1 calc R . . C2G C -0.14953(18) 0.8324(2) 0.00033(13) 0.0643(6) Uani 1 1 d . . . H2G H -0.1536 0.7477 -0.0043 0.077 Uiso 1 1 calc R . . O1 O -0.06544(10) 0.69967(12) 0.16339(7) 0.0528(4) Uani 1 1 d D . . C11G C 0.05822(18) 0.9707(3) 0.17100(13) 0.0770(8) Uani 1 1 d . . . H11A H 0.1010 1.0200 0.2065 0.115 Uiso 1 1 calc R . . H11B H 0.0956 0.9201 0.1478 0.115 Uiso 1 1 calc R . . H11C H 0.0196 0.9200 0.1932 0.115 Uiso 1 1 calc R . . H1 H -0.0607(18) 0.7596(18) 0.1284(10) 0.100(9) 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 C1 0.0301(9) 0.0328(9) 0.0383(10) -0.0027(8) 0.0108(8) -0.0032(7) C9 0.0350(10) 0.0387(10) 0.0460(11) -0.0075(8) 0.0135(8) -0.0035(8) C10 0.0269(9) 0.0330(9) 0.0418(10) -0.0070(8) 0.0073(8) -0.0027(7) C2 0.0378(10) 0.0335(10) 0.0484(11) 0.0028(8) 0.0162(9) 0.0012(8) C8 0.0384(10) 0.0477(11) 0.0402(10) -0.0018(9) 0.0075(8) 0.0061(9) C3 0.0560(13) 0.0471(12) 0.0512(12) 0.0090(9) 0.0245(10) 0.0015(10) C5 0.0391(11) 0.0552(13) 0.0609(13) -0.0160(11) 0.0214(10) -0.0012(10) C7 0.0449(12) 0.0536(13) 0.0505(12) 0.0005(10) -0.0013(10) 0.0137(10) C6 0.0395(11) 0.0612(14) 0.0661(15) -0.0150(12) 0.0083(11) 0.0138(10) C4 0.0556(13) 0.0489(12) 0.0566(13) -0.0026(10) 0.0336(11) -0.0034(10) C10G 0.0413(11) 0.0388(11) 0.0445(10) 0.0064(9) 0.0180(9) 0.0048(9) C9G 0.0438(11) 0.0613(13) 0.0451(12) 0.0090(10) 0.0186(10) 0.0059(10) N1G 0.0570(11) 0.0510(11) 0.0577(11) 0.0061(9) 0.0188(9) 0.0028(9) C8G 0.0508(13) 0.0633(15) 0.0454(12) 0.0001(10) 0.0132(10) -0.0013(11) C5G 0.0615(14) 0.0483(13) 0.0697(15) 0.0189(12) 0.0340(13) 0.0147(11) C4G 0.0575(14) 0.0804(18) 0.0511(13) 0.0177(13) 0.0097(12) 0.0072(13) C6G 0.0780(17) 0.0487(13) 0.0783(17) 0.0015(13) 0.0377(15) 0.0016(13) C3G 0.0721(17) 0.088(2) 0.0551(15) -0.0043(14) 0.0022(13) -0.0152(15) C7G 0.0684(16) 0.0614(15) 0.0673(16) -0.0095(12) 0.0211(13) -0.0088(13) C2G 0.0733(16) 0.0564(14) 0.0636(15) -0.0063(12) 0.0186(14) -0.0127(12) O1 0.0526(8) 0.0498(9) 0.0628(9) 0.0181(7) 0.0269(7) 0.0168(7) C11G 0.0657(16) 0.097(2) 0.0569(14) 0.0161(14) -0.0045(12) 0.0111(14) _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 C1 C2 1.375(2) . ? C1 C10 1.427(2) . ? C1 C1 1.503(3) 2 ? C9 C4 1.410(3) . ? C9 C5 1.420(3) . ? C9 C10 1.425(2) . ? C10 C8 1.413(3) . ? C2 O1 1.363(2) . ? C2 C3 1.418(2) . ? C8 C7 1.369(3) . ? C8 H8 0.9400 . ? C3 C4 1.357(3) . ? C3 H3 0.9400 . ? C5 C6 1.352(3) . ? C5 H5 0.9400 . ? C7 C6 1.395(3) . ? C7 H7 0.9400 . ? C6 H6 0.9400 . ? C4 H4 0.9400 . ? C10G N1G 1.376(3) . ? C10G C8G 1.409(3) . ? C10G C9G 1.431(3) . ? C9G C4G 1.385(3) . ? C9G C5G 1.415(3) . ? N1G C2G 1.323(3) . ? C8G C7G 1.354(3) . ? C8G C11G 1.513(3) . ? C5G C6G 1.346(3) . ? C5G H5G 0.9400 . ? C4G C3G 1.365(3) . ? C4G H4G 0.9400 . ? C6G C7G 1.411(3) . ? C6G H6G 0.9400 . ? C3G C2G 1.384(4) . ? C3G H3G 0.9400 . ? C7G H7G 0.9400 . ? C2G H2G 0.9400 . ? O1 H1 0.969(8) . ? C11G H11A 0.9700 . ? C11G H11B 0.9700 . ? C11G H11C 0.9700 . ? 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 C2 C1 C10 118.91(15) . . ? C2 C1 C1 120.52(14) . 2 ? C10 C1 C1 120.57(14) . 2 ? C4 C9 C5 122.63(17) . . ? C4 C9 C10 118.34(16) . . ? C5 C9 C10 119.02(18) . . ? C8 C10 C9 117.53(16) . . ? C8 C10 C1 122.23(16) . . ? C9 C10 C1 120.24(16) . . ? O1 C2 C1 119.42(15) . . ? O1 C2 C3 119.88(16) . . ? C1 C2 C3 120.70(16) . . ? C7 C8 C10 121.38(18) . . ? C7 C8 H8 119.3 . . ? C10 C8 H8 119.3 . . ? C4 C3 C2 120.67(18) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C6 C5 C9 121.47(18) . . ? C6 C5 H5 119.3 . . ? C9 C5 H5 119.3 . . ? C8 C7 C6 120.8(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C5 C6 C7 119.77(19) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C3 C4 C9 121.14(17) . . ? C3 C4 H4 119.4 . . ? C9 C4 H4 119.4 . . ? N1G C10G C8G 119.83(18) . . ? N1G C10G C9G 120.26(18) . . ? C8G C10G C9G 119.88(18) . . ? C4G C9G C5G 122.5(2) . . ? C4G C9G C10G 118.9(2) . . ? C5G C9G C10G 118.7(2) . . ? C2G N1G C10G 117.56(19) . . ? C7G C8G C10G 118.8(2) . . ? C7G C8G C11G 121.5(2) . . ? C10G C8G C11G 119.7(2) . . ? C6G C5G C9G 120.2(2) . . ? C6G C5G H5G 119.9 . . ? C9G C5G H5G 119.9 . . ? C3G C4G C9G 119.9(2) . . ? C3G C4G H4G 120.0 . . ? C9G C4G H4G 120.0 . . ? C5G C6G C7G 120.5(2) . . ? C5G C6G H6G 119.7 . . ? C7G C6G H6G 119.7 . . ? C4G C3G C2G 118.2(2) . . ? C4G C3G H3G 120.9 . . ? C2G C3G H3G 120.9 . . ? C8G C7G C6G 122.0(2) . . ? C8G C7G H7G 119.0 . . ? C6G C7G H7G 119.0 . . ? N1G C2G C3G 125.1(2) . . ? N1G C2G H2G 117.4 . . ? C3G C2G H2G 117.4 . . ? C2 O1 H1 107.6(15) . . ? C8G C11G H11A 109.5 . . ? C8G C11G H11B 109.5 . . ? H11A C11G H11B 109.5 . . ? C8G C11G H11C 109.5 . . ? H11A C11G H11C 109.5 . . ? H11B C11G H11C 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 C4 C9 C10 C8 178.30(17) . . . . ? C5 C9 C10 C8 -0.7(2) . . . . ? C4 C9 C10 C1 -1.1(2) . . . . ? C5 C9 C10 C1 179.85(16) . . . . ? C2 C1 C10 C8 -178.93(16) . . . . ? C1 C1 C10 C8 0.6(3) 2 . . . ? C2 C1 C10 C9 0.5(2) . . . . ? C1 C1 C10 C9 -179.96(16) 2 . . . ? C10 C1 C2 O1 179.70(15) . . . . ? C1 C1 C2 O1 0.1(3) 2 . . . ? C10 C1 C2 C3 0.6(3) . . . . ? C1 C1 C2 C3 -179.01(17) 2 . . . ? C9 C10 C8 C7 0.1(3) . . . . ? C1 C10 C8 C7 179.46(17) . . . . ? O1 C2 C3 C4 179.94(18) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C4 C9 C5 C6 -178.12(19) . . . . ? C10 C9 C5 C6 0.9(3) . . . . ? C10 C8 C7 C6 0.5(3) . . . . ? C9 C5 C6 C7 -0.3(3) . . . . ? C8 C7 C6 C5 -0.4(3) . . . . ? C2 C3 C4 C9 0.2(3) . . . . ? C5 C9 C4 C3 179.76(19) . . . . ? C10 C9 C4 C3 0.8(3) . . . . ? N1G C10G C9G C4G -0.2(3) . . . . ? C8G C10G C9G C4G 177.81(18) . . . . ? N1G C10G C9G C5G -179.03(16) . . . . ? C8G C10G C9G C5G -1.0(3) . . . . ? C8G C10G N1G C2G -175.47(18) . . . . ? C9G C10G N1G C2G 2.5(3) . . . . ? N1G C10G C8G C7G 177.95(18) . . . . ? C9G C10G C8G C7G 0.0(3) . . . . ? N1G C10G C8G C11G -0.6(3) . . . . ? C9G C10G C8G C11G -178.60(18) . . . . ? C4G C9G C5G C6G -177.0(2) . . . . ? C10G C9G C5G C6G 1.8(3) . . . . ? C5G C9G C4G C3G 176.7(2) . . . . ? C10G C9G C4G C3G -2.1(3) . . . . ? C9G C5G C6G C7G -1.5(3) . . . . ? C9G C4G C3G C2G 1.9(4) . . . . ? C10G C8G C7G C6G 0.4(3) . . . . ? C11G C8G C7G C6G 178.9(2) . . . . ? C5G C6G C7G C8G 0.3(3) . . . . ? C10G N1G C2G C3G -2.8(3) . . . . ? C4G C3G C2G N1G 0.6(4) . . . . ? 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 N1G 0.97(2) 1.89(2) 2.833(2) 165(2) . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.372 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.037