# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Marina Fonari' _publ_contact_author_address ; X-ray laboratory Institute of Applied Physics Academy of Sciences of Moldova Academy str., 5 Chisinau MD2028 MOLDOVA ; _publ_contact_author_email FONARI.XRAY@PHYS.ASM.MD _publ_section_title ; 2,4-Dithiouracil: the reproducible H-bonded structural motifs in the complexes with 18-membered crown ethers ; loop_ _publ_author_name 'Marina Fonari' 'Gabriele Bocelli' 'Eduard V. Ganin' 'Yurii A. Simonov' 'Wen-Jwu Wang' data_dtu1 _database_code_depnum_ccdc_archive 'CCDC 268384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4,7,10,13,16-hexaoxacyclooctadecane pyrimidine-2,4(1H,3H)-dithione monohydrate ; _chemical_name_common ; 1,4,7,10,13,16-hexaoxacyclooctadecane pyrimidine-2,4(1H,3H)- dithione monohydrate ; _chemical_melting_point 265 _chemical_formula_moiety 'C12 H24 O6, C4 H4 N2 S2, H2 O' _chemical_formula_sum 'C16 H30 N2 O7 S2' _chemical_formula_weight 426.54 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7070(15) _cell_length_b 17.374(4) _cell_length_c 16.622(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.17(3) _cell_angle_gamma 90.00 _cell_volume 2224.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.22 _cell_measurement_theta_max 17.90 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9121 _exptl_absorpt_correction_T_max 0.9444 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips Pw100' _diffrn_measurement_method 'omega-2theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4524 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4380 _reflns_number_gt 3152 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0719P)^2^+0.2350P] 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 4380 _refine_ls_number_parameters 256 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.089 _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 S1 S 0.83374(8) 0.39910(3) 0.34792(3) 0.05751(19) Uani 1 1 d . . . S2 S 0.90385(9) 0.09654(3) 0.32263(3) 0.0611(2) Uani 1 1 d . . . N1U N 0.85880(18) 0.24579(8) 0.34830(8) 0.0339(3) Uani 1 1 d D . . H1U H 0.893(3) 0.2521(12) 0.3038(10) 0.051 Uiso 1 1 d D . . N2U N 0.7549(2) 0.30024(10) 0.46245(9) 0.0410(4) Uani 1 1 d D . . H2U H 0.721(3) 0.3391(10) 0.4874(13) 0.062 Uiso 1 1 d D . . C1U C 0.8146(2) 0.31173(10) 0.38777(10) 0.0349(4) Uani 1 1 d . . . C2U C 0.8470(2) 0.17167(10) 0.37762(10) 0.0362(4) Uani 1 1 d . . . C3U C 0.7848(3) 0.16582(11) 0.45675(11) 0.0439(5) Uani 1 1 d . . . H3U H 0.7749 0.1179 0.4811 0.053 Uiso 1 1 calc R . . C4U C 0.7407(3) 0.22962(12) 0.49606(11) 0.0465(5) Uani 1 1 d . . . H4U H 0.6992 0.2254 0.5477 0.056 Uiso 1 1 calc R . . O1 O 0.9162(2) 0.32898(9) 0.64854(9) 0.0605(4) Uani 1 1 d . . . C2 C 0.9858(4) 0.28521(18) 0.71391(19) 0.0942(10) Uani 1 1 d . . . H2A H 0.9097 0.2891 0.7589 0.113 Uiso 1 1 calc R . . H2B H 1.0981 0.3060 0.7309 0.113 Uiso 1 1 calc R . . C3 C 1.0052(4) 0.20461(19) 0.6919(2) 0.0909(9) Uani 1 1 d . . . H3A H 1.0577 0.2010 0.6400 0.109 Uiso 1 1 calc R . . H3B H 1.0812 0.1791 0.7314 0.109 Uiso 1 1 calc R . . O4 O 0.8400(2) 0.16735(9) 0.68838(10) 0.0670(5) Uani 1 1 d . . . C5 C 0.8564(4) 0.08763(14) 0.67455(16) 0.0780(8) Uani 1 1 d . . . H5A H 0.9269 0.0644 0.7176 0.094 Uiso 1 1 calc R . . H5B H 0.9131 0.0789 0.6242 0.094 Uiso 1 1 calc R . . C6 C 0.6823(4) 0.05225(14) 0.67100(15) 0.0821(9) Uani 1 1 d . . . H6A H 0.6928 -0.0033 0.6688 0.099 Uiso 1 1 calc R . . H6B H 0.6209 0.0656 0.7189 0.099 Uiso 1 1 calc R . . O7 O 0.5880(2) 0.07928(9) 0.60152(10) 0.0662(5) Uani 1 1 d . . . C8 C 0.4120(4) 0.05721(14) 0.6000(2) 0.0863(9) Uani 1 1 d . . . H8A H 0.3571 0.0756 0.6479 0.104 Uiso 1 1 calc R . . H8B H 0.4022 0.0016 0.5983 0.104 Uiso 1 1 calc R . . C9 C 0.3265(4) 0.09157(18) 0.5270(2) 0.0979(11) Uani 1 1 d . . . H9A H 0.3951 0.0810 0.4805 0.118 Uiso 1 1 calc R . . H9B H 0.2127 0.0687 0.5177 0.118 Uiso 1 1 calc R . . O10 O 0.3096(2) 0.17287(10) 0.53730(12) 0.0780(5) Uani 1 1 d . . . C11 C 0.2823(4) 0.2163(2) 0.46502(18) 0.0954(10) Uani 1 1 d . . . H11A H 0.1852 0.1951 0.4334 0.114 Uiso 1 1 calc R . . H11B H 0.3848 0.2139 0.4330 0.114 Uiso 1 1 calc R . . C12 C 0.2452(4) 0.2980(2) 0.4870(2) 0.0930(10) Uani 1 1 d . . . H12A H 0.2258 0.3285 0.4386 0.112 Uiso 1 1 calc R . . H12B H 0.1415 0.3004 0.5182 0.112 Uiso 1 1 calc R . . O13 O 0.38787(19) 0.32708(9) 0.53231(11) 0.0661(5) Uani 1 1 d . . . C14 C 0.3706(3) 0.40575(14) 0.5567(2) 0.0837(9) Uani 1 1 d . . . H14A H 0.2652 0.4119 0.5862 0.100 Uiso 1 1 calc R . . H14B H 0.3623 0.4387 0.5096 0.100 Uiso 1 1 calc R . . C15 C 0.5207(4) 0.42821(14) 0.60773(16) 0.0713(7) Uani 1 1 d . . . H15A H 0.5055 0.4802 0.6274 0.086 Uiso 1 1 calc R . . H15B H 0.5323 0.3940 0.6537 0.086 Uiso 1 1 calc R . . O16 O 0.67023(19) 0.42417(8) 0.56227(8) 0.0504(4) Uani 1 1 d . . . C17 C 0.8272(3) 0.45128(13) 0.60243(16) 0.0694(7) Uani 1 1 d . . . H17A H 0.8087 0.5038 0.6200 0.083 Uiso 1 1 calc R . . H17B H 0.9185 0.4523 0.5639 0.083 Uiso 1 1 calc R . . C18 C 0.8867(4) 0.40592(14) 0.67159(18) 0.0764(8) Uani 1 1 d . . . H18A H 0.9933 0.4278 0.6945 0.092 Uiso 1 1 calc R . . H18B H 0.8001 0.4073 0.7124 0.092 Uiso 1 1 calc R . . O1W O 0.9930(2) 0.26086(9) 0.19317(9) 0.0629(5) Uani 1 1 d D . . H1W H 0.940(3) 0.2604(16) 0.1481(13) 0.094 Uiso 1 1 d D . . H2W H 1.090(3) 0.2827(16) 0.1953(16) 0.094 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 S1 0.0813(4) 0.0346(3) 0.0575(3) -0.0014(2) 0.0149(3) -0.0066(3) S2 0.0913(5) 0.0369(3) 0.0569(3) -0.0051(2) 0.0257(3) 0.0062(3) N1U 0.0379(8) 0.0348(8) 0.0295(7) -0.0014(6) 0.0064(6) -0.0032(6) N2U 0.0429(9) 0.0442(9) 0.0365(8) -0.0087(7) 0.0086(7) 0.0010(7) C1U 0.0305(9) 0.0388(10) 0.0354(9) -0.0058(7) 0.0004(7) -0.0037(7) C2U 0.0339(9) 0.0387(10) 0.0362(9) -0.0014(8) 0.0026(7) -0.0023(7) C3U 0.0503(11) 0.0435(11) 0.0386(10) 0.0071(8) 0.0090(8) -0.0014(9) C4U 0.0507(12) 0.0574(12) 0.0323(9) 0.0013(9) 0.0123(8) -0.0039(10) O1 0.0596(10) 0.0570(9) 0.0636(10) -0.0098(7) -0.0144(8) 0.0075(7) C2 0.096(2) 0.095(2) 0.088(2) 0.0024(17) -0.0489(18) -0.0019(18) C3 0.0668(18) 0.094(2) 0.109(2) 0.0230(19) -0.0285(16) 0.0174(16) O4 0.0764(12) 0.0591(10) 0.0655(10) 0.0087(8) 0.0013(8) 0.0209(8) C5 0.109(2) 0.0577(15) 0.0674(16) 0.0189(12) 0.0080(15) 0.0364(15) C6 0.144(3) 0.0400(13) 0.0652(16) 0.0182(11) 0.0393(17) 0.0159(15) O7 0.0815(12) 0.0468(9) 0.0725(11) 0.0103(8) 0.0314(9) -0.0040(8) C8 0.092(2) 0.0408(13) 0.130(3) -0.0143(15) 0.0538(19) -0.0182(14) C9 0.0645(18) 0.090(2) 0.141(3) -0.059(2) 0.0191(19) -0.0277(15) O10 0.0727(12) 0.0756(12) 0.0865(13) -0.0209(10) 0.0122(10) -0.0076(9) C11 0.0536(16) 0.152(3) 0.079(2) -0.015(2) -0.0237(14) -0.0222(18) C12 0.0510(16) 0.118(3) 0.108(2) 0.029(2) -0.0218(15) 0.0029(16) O13 0.0410(8) 0.0721(11) 0.0849(11) 0.0145(9) -0.0030(8) 0.0104(7) C14 0.0548(15) 0.0578(16) 0.141(3) 0.0319(16) 0.0319(16) 0.0254(12) C15 0.0859(19) 0.0490(13) 0.0819(17) -0.0025(12) 0.0406(15) 0.0075(12) O16 0.0604(9) 0.0430(7) 0.0483(8) -0.0045(6) 0.0078(7) 0.0076(6) C17 0.0787(17) 0.0482(13) 0.0805(17) -0.0141(12) -0.0059(14) -0.0126(12) C18 0.0820(19) 0.0595(16) 0.0860(19) -0.0250(14) -0.0196(15) -0.0019(13) O1W 0.0835(12) 0.0612(10) 0.0456(8) -0.0031(8) 0.0234(8) -0.0182(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 S1 C1U 1.6649(18) . ? S2 C2U 1.6620(18) . ? N1U C1U 1.370(2) . ? N1U C2U 1.381(2) . ? N1U H1U 0.802(15) . ? N2U C4U 1.354(3) . ? N2U C1U 1.355(2) . ? N2U H2U 0.838(15) . ? C2U C3U 1.421(3) . ? C3U C4U 1.337(3) . ? C3U H3U 0.9300 . ? C4U H4U 0.9300 . ? O1 C18 1.411(3) . ? O1 C2 1.415(3) . ? C2 C3 1.456(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O4 1.428(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C5 1.411(3) . ? C5 C6 1.476(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O7 1.421(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O7 C8 1.409(3) . ? C8 C9 1.484(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O10 1.429(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? O10 C11 1.427(4) . ? C11 C12 1.496(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O13 1.404(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O13 C14 1.433(3) . ? C14 C15 1.461(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 O16 1.403(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? O16 C17 1.439(3) . ? C17 C18 1.454(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? O1W H1W 0.841(16) . ? O1W H2W 0.837(16) . ? 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 C1U N1U C2U 126.15(15) . . ? C1U N1U H1U 115.1(15) . . ? C2U N1U H1U 118.7(15) . . ? C4U N2U C1U 123.17(16) . . ? C4U N2U H2U 119.6(16) . . ? C1U N2U H2U 117.2(16) . . ? N2U C1U N1U 114.51(15) . . ? N2U C1U S1 122.49(14) . . ? N1U C1U S1 123.00(13) . . ? N1U C2U C3U 115.00(16) . . ? N1U C2U S2 121.06(13) . . ? C3U C2U S2 123.93(14) . . ? C4U C3U C2U 119.61(17) . . ? C4U C3U H3U 120.2 . . ? C2U C3U H3U 120.2 . . ? C3U C4U N2U 121.56(17) . . ? C3U C4U H4U 119.2 . . ? N2U C4U H4U 119.2 . . ? C18 O1 C2 111.1(2) . . ? O1 C2 C3 111.3(2) . . ? O1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? O1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? O4 C3 C2 110.3(3) . . ? O4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 O4 C3 111.5(2) . . ? O4 C5 C6 109.2(2) . . ? O4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? O4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? O7 C6 C5 109.33(19) . . ? O7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? O7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C8 O7 C6 112.7(2) . . ? O7 C8 C9 107.6(2) . . ? O7 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? O7 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? O10 C9 C8 109.9(2) . . ? O10 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? O10 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 O10 C9 115.6(3) . . ? O10 C11 C12 108.6(2) . . ? O10 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? O10 C11 H11B 110.0 . . ? C12 C11 H11B 110.0 . . ? H11A C11 H11B 108.3 . . ? O13 C12 C11 108.7(2) . . ? O13 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? O13 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.3 . . ? C12 O13 C14 114.6(2) . . ? O13 C14 C15 109.81(19) . . ? O13 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? O13 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? O16 C15 C14 108.8(2) . . ? O16 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? O16 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C15 O16 C17 115.3(2) . . ? O16 C17 C18 115.1(2) . . ? O16 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? O16 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? O1 C18 C17 110.4(2) . . ? O1 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? O1 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? H1W O1W H2W 116(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 C4U N2U C1U N1U 0.4(2) . . . . ? C4U N2U C1U S1 -179.12(15) . . . . ? C2U N1U C1U N2U 0.2(2) . . . . ? C2U N1U C1U S1 179.77(14) . . . . ? C1U N1U C2U C3U -0.9(3) . . . . ? C1U N1U C2U S2 179.47(13) . . . . ? N1U C2U C3U C4U 1.0(3) . . . . ? S2 C2U C3U C4U -179.39(16) . . . . ? C2U C3U C4U N2U -0.5(3) . . . . ? C1U N2U C4U C3U -0.3(3) . . . . ? C18 O1 C2 C3 176.1(3) . . . . ? O1 C2 C3 O4 -75.0(4) . . . . ? C2 C3 O4 C5 -174.5(2) . . . . ? C3 O4 C5 C6 -179.7(2) . . . . ? O4 C5 C6 O7 67.1(3) . . . . ? C5 C6 O7 C8 -171.1(2) . . . . ? C6 O7 C8 C9 177.5(2) . . . . ? O7 C8 C9 O10 -71.7(3) . . . . ? C8 C9 O10 C11 160.8(2) . . . . ? C9 O10 C11 C12 172.9(2) . . . . ? O10 C11 C12 O13 59.8(3) . . . . ? C11 C12 O13 C14 179.3(2) . . . . ? C12 O13 C14 C15 176.3(2) . . . . ? O13 C14 C15 O16 63.5(3) . . . . ? C14 C15 O16 C17 174.72(18) . . . . ? C15 O16 C17 C18 65.6(3) . . . . ? C2 O1 C18 C17 175.9(2) . . . . ? O16 C17 C18 O1 58.6(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 N2U H2U O16 0.838(15) 1.982(16) 2.810(2) 170(2) . N1U H1U O1W 0.802(15) 2.027(16) 2.826(2) 175(2) . C3U H3U O7 0.93 2.60 3.260(2) 128.6 . O1W H1W O10 0.841(16) 2.37(2) 3.124(3) 150(2) 4_665 O1W H1W O13 0.841(16) 2.47(2) 3.158(2) 139(2) 4_665 O1W H2W O4 0.837(16) 2.122(17) 2.955(2) 174(3) 4_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.432 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.051 data_dtu2 _database_code_depnum_ccdc_archive 'CCDC 268385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis-anti-cis (B) isomer (2,3,11,12-Dicyclohexano-1,4,7,10,13,16-hexaoxacyclooctadecane) bis(pyrimidine-2,4(1H,3H)-dithione) clathrate ; _chemical_name_common ; cis-anti-cis (B) isomer (2,3,11,12-Dicyclohexano- 1,4,7,10,13,16-hexaoxacyclooctadecane) bis(pyrimidine-2,4(1H,3H)- dithione) clathrate ; _chemical_melting_point '>250 (decomp)' _chemical_formula_moiety 'C20 H36 O6, 2(C4 H4 N2 S2)' _chemical_formula_sum 'C28 H44 N4 O6 S4' _chemical_formula_weight 660.91 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.624(2) _cell_length_b 12.698(3) _cell_length_c 12.093(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.69(3) _cell_angle_gamma 90.00 _cell_volume 1680.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 7.04 _cell_measurement_theta_max 16.39 _exptl_crystal_description 'triangular based pyramidal crystal' _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips Pw1100' _diffrn_measurement_method 'omega-2theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 3454 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0839 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3302 _reflns_number_gt 1669 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0654P)^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 3302 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1279 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _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 S1 S -0.30300(8) 0.48215(8) 0.04043(8) 0.0490(3) Uani 1 1 d . . . S2 S -0.58712(8) 0.54266(9) 0.29474(9) 0.0596(3) Uani 1 1 d . . . N1U N -0.4253(2) 0.5128(2) 0.1887(2) 0.0325(6) Uani 1 1 d D . . H1U H -0.485(2) 0.503(3) 0.126(2) 0.049 Uiso 1 1 d D . . N2U N -0.2179(2) 0.5240(2) 0.2705(2) 0.0365(7) Uani 1 1 d D . . H2U H -0.150(2) 0.523(3) 0.257(3) 0.055 Uiso 1 1 d D . . C1U C -0.3154(3) 0.5064(2) 0.1712(3) 0.0324(8) Uani 1 1 d . . . C2U C -0.4462(3) 0.5362(3) 0.2918(3) 0.0361(8) Uani 1 1 d . . . C3U C -0.3377(3) 0.5537(3) 0.3888(3) 0.0466(9) Uani 1 1 d . . . H3U H -0.3429 0.5693 0.4621 0.056 Uiso 1 1 calc R . . C4U C -0.2285(3) 0.5479(3) 0.3755(3) 0.0443(9) Uani 1 1 d . . . H4U H -0.1584 0.5605 0.4396 0.053 Uiso 1 1 calc R . . O1 O -0.02386(19) 0.71626(18) 0.37876(18) 0.0413(6) Uani 1 1 d . . . C2 C 0.0776(3) 0.7199(3) 0.4854(3) 0.0471(9) Uani 1 1 d . . . H2A H 0.1296 0.7791 0.4836 0.057 Uiso 1 1 calc R . . H2B H 0.1253 0.6559 0.4936 0.057 Uiso 1 1 calc R . . C3 C 0.0338(3) 0.7308(3) 0.5878(3) 0.0478(10) Uani 1 1 d . . . H3A H 0.1011 0.7525 0.6565 0.057 Uiso 1 1 calc R . . H3B H -0.0289 0.7847 0.5711 0.057 Uiso 1 1 calc R . . O4 O -0.0147(2) 0.63343(17) 0.61126(18) 0.0392(6) Uani 1 1 d . . . C5 C -0.0381(3) 0.6368(3) 0.7193(3) 0.0438(9) Uani 1 1 d . . . H5A H -0.0868 0.6985 0.7207 0.053 Uiso 1 1 calc R . . H5B H 0.0385 0.6423 0.7840 0.053 Uiso 1 1 calc R . . C6 C -0.1042(3) 0.5405(3) 0.7339(3) 0.0452(9) Uani 1 1 d . . . H6A H -0.1295 0.5479 0.8022 0.054 Uiso 1 1 calc R . . H6B H -0.1768 0.5308 0.6655 0.054 Uiso 1 1 calc R . . O7 O -0.02618(17) 0.45128(18) 0.74811(18) 0.0364(6) Uani 1 1 d . . . C8 C -0.0891(3) 0.3527(3) 0.7451(3) 0.0385(8) Uani 1 1 d . . . H8 H -0.1667 0.3543 0.6795 0.046 Uiso 1 1 calc R . . C9 C -0.0095(3) 0.2659(3) 0.7234(3) 0.0362(8) Uani 1 1 d . . . H9 H -0.0565 0.2003 0.7110 0.043 Uiso 1 1 calc R . . C10 C 0.1064(3) 0.2491(3) 0.8271(3) 0.0446(9) Uani 1 1 d . . . H10A H 0.1577 0.3112 0.8379 0.054 Uiso 1 1 calc R . . H10B H 0.1513 0.1900 0.8111 0.054 Uiso 1 1 calc R . . C11 C 0.0782(3) 0.2278(3) 0.9392(3) 0.0561(11) Uani 1 1 d . . . H11A H 0.0347 0.1615 0.9318 0.067 Uiso 1 1 calc R . . H11B H 0.1540 0.2220 1.0049 0.067 Uiso 1 1 calc R . . C12 C 0.0011(4) 0.3158(3) 0.9625(3) 0.0600(11) Uani 1 1 d . . . H12A H 0.0480 0.3806 0.9779 0.072 Uiso 1 1 calc R . . H12B H -0.0197 0.2989 1.0317 0.072 Uiso 1 1 calc R . . C13 C -0.1154(3) 0.3318(3) 0.8585(3) 0.0537(10) Uani 1 1 d . . . H13A H -0.1605 0.3908 0.8744 0.064 Uiso 1 1 calc R . . H13B H -0.1663 0.2695 0.8486 0.064 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 S1 0.0302(5) 0.0767(8) 0.0379(5) -0.0128(5) 0.0084(4) -0.0031(5) S2 0.0303(5) 0.0968(9) 0.0523(6) -0.0022(6) 0.0146(4) 0.0067(5) N1U 0.0196(14) 0.0430(17) 0.0292(15) -0.0028(13) 0.0007(11) -0.0016(13) N2U 0.0172(13) 0.051(2) 0.0348(15) -0.0006(14) 0.0008(11) -0.0012(13) C1U 0.0206(15) 0.0328(19) 0.0379(18) -0.0003(15) 0.0022(13) -0.0008(14) C2U 0.0283(17) 0.042(2) 0.0344(17) 0.0023(16) 0.0062(14) -0.0021(16) C3U 0.037(2) 0.064(3) 0.0341(19) -0.0071(18) 0.0065(16) -0.0037(19) C4U 0.0307(19) 0.061(3) 0.0307(18) -0.0020(17) -0.0031(14) -0.0088(18) O1 0.0391(13) 0.0521(15) 0.0287(12) -0.0021(11) 0.0063(10) -0.0065(12) C2 0.041(2) 0.054(2) 0.038(2) -0.0002(18) 0.0021(16) -0.0118(18) C3 0.062(3) 0.041(2) 0.0323(19) -0.0051(17) 0.0046(18) -0.0091(19) O4 0.0479(14) 0.0374(14) 0.0293(12) -0.0067(10) 0.0091(10) -0.0026(11) C5 0.048(2) 0.045(2) 0.040(2) -0.0073(17) 0.0168(17) 0.0031(18) C6 0.040(2) 0.056(3) 0.043(2) -0.0035(19) 0.0188(16) 0.0069(19) O7 0.0243(11) 0.0447(15) 0.0386(12) 0.0001(11) 0.0084(10) 0.0029(11) C8 0.0284(17) 0.053(2) 0.0316(18) -0.0001(16) 0.0063(15) -0.0088(17) C9 0.0338(18) 0.039(2) 0.0348(19) -0.0021(16) 0.0105(15) -0.0068(16) C10 0.043(2) 0.045(2) 0.0392(19) 0.0058(17) 0.0054(16) 0.0043(17) C11 0.051(2) 0.070(3) 0.040(2) 0.011(2) 0.0062(18) 0.003(2) C12 0.067(3) 0.083(3) 0.032(2) 0.001(2) 0.019(2) -0.005(2) C13 0.042(2) 0.073(3) 0.052(2) 0.006(2) 0.0229(18) 0.001(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 S1 C1U 1.665(3) . ? S2 C2U 1.653(3) . ? N1U C1U 1.366(4) . ? N1U C2U 1.379(4) . ? N1U H1U 0.851(17) . ? N2U C4U 1.350(4) . ? N2U C1U 1.364(4) . ? N2U H2U 0.861(18) . ? C2U C3U 1.421(4) . ? C3U C4U 1.335(4) . ? C3U H3U 0.9300 . ? C4U H4U 0.9300 . ? O1 C2 1.425(4) . ? O1 C9 1.431(4) 3_566 ? C2 C3 1.495(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O4 1.426(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C5 1.422(4) . ? C5 C6 1.487(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O7 1.425(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O7 C8 1.444(4) . ? C8 C9 1.518(4) . ? C8 C13 1.526(4) . ? C8 H8 0.9800 . ? C9 O1 1.431(4) 3_566 ? C9 C10 1.515(4) . ? C9 H9 0.9800 . ? C10 C11 1.522(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.517(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.520(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 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 C1U N1U C2U 127.7(3) . . ? C1U N1U H1U 112(2) . . ? C2U N1U H1U 120(2) . . ? C4U N2U C1U 123.6(3) . . ? C4U N2U H2U 124(2) . . ? C1U N2U H2U 112(2) . . ? N2U C1U N1U 113.4(3) . . ? N2U C1U S1 123.7(2) . . ? N1U C1U S1 122.9(2) . . ? N1U C2U C3U 113.7(3) . . ? N1U C2U S2 120.5(2) . . ? C3U C2U S2 125.8(3) . . ? C4U C3U C2U 120.5(3) . . ? C4U C3U H3U 119.8 . . ? C2U C3U H3U 119.8 . . ? C3U C4U N2U 121.2(3) . . ? C3U C4U H4U 119.4 . . ? N2U C4U H4U 119.4 . . ? C2 O1 C9 113.2(2) . 3_566 ? O1 C2 C3 110.1(3) . . ? O1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? O1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.2 . . ? O4 C3 C2 110.6(3) . . ? O4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? O4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 O4 C3 111.5(2) . . ? O4 C5 C6 110.5(3) . . ? O4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? O4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O7 C6 C5 109.6(3) . . ? O7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? O7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C6 O7 C8 112.9(2) . . ? O7 C8 C9 107.5(2) . . ? O7 C8 C13 112.4(3) . . ? C9 C8 C13 110.3(3) . . ? O7 C8 H8 108.8 . . ? C9 C8 H8 108.8 . . ? C13 C8 H8 108.8 . . ? O1 C9 C10 108.2(3) 3_566 . ? O1 C9 C8 113.1(3) 3_566 . ? C10 C9 C8 112.5(3) . . ? O1 C9 H9 107.6 3_566 . ? C10 C9 H9 107.6 . . ? C8 C9 H9 107.6 . . ? C9 C10 C11 111.3(3) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 110.6(3) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.2(3) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C8 112.0(3) . . ? C12 C13 H13A 109.2 . . ? C8 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C8 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? 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 C2 C3 O4 74.8(4) . . . . ? C2 C3 O4 C5 170.3(3) . . . . ? C3 O4 C5 C6 172.1(3) . . . . ? O4 C5 C6 O7 67.2(3) . . . . ? C5 C6 O7 C8 -171.2(3) . . . . ? C6 O7 C8 C9 162.9(2) . . . . ? O7 C8 C9 O1 -54.1(3) . . . 3_566 ? C8 C9 O1 C2 -66.1(3) . . 3_566 3_566 ? C9 O1 C2 C3 -164.3(3) . 3_566 3_566 3_566 ? 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 N1U H1U S1 0.851(17) 2.61(2) 3.430(3) 163(3) 3_465 N2U H2U O7 0.861(18) 2.09(2) 2.938(3) 167(3) 3_566 C4U H4U O4 0.93 2.37 3.273(4) 163.4 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.317 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.063 data_dtu3 _database_code_depnum_ccdc_archive 'CCDC 268386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; cis-syn-cis (A) isomer (2,3,11,12-Dicyclohexano-1,4,7,10,13,16-hexaoxacyclooctadecane) pyrimidine-2,4(1H,3H)-dithione monohydrate ; _chemical_name_common ; cis-syn-cis (A) isomer (2,3,11,12-Dicyclohexano- 1,4,7,10,13,16-hexaoxacyclooctadecane) pyrimidine-2,4(1H,3H)-dithione monohydrate ; _chemical_melting_point >260(decomp) _chemical_formula_moiety 'C20 H36 O6, C4 H4 N2 S2, H2 O' _chemical_formula_sum 'C24 H42 N2 O7 S2' _chemical_formula_weight 534.72 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9880(16) _cell_length_b 21.627(4) _cell_length_c 16.439(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.17(3) _cell_angle_gamma 90.00 _cell_volume 2835.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 4.69 _cell_measurement_theta_max 12.61 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips Pw1100' _diffrn_measurement_method 'omega-2theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5741 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.2743 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5555 _reflns_number_gt 1556 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0221P)^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 5555 _refine_ls_number_parameters 322 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2645 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 0.709 _refine_ls_restrained_S_all 0.709 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 S1 S 1.20392(15) 0.86034(5) 0.37252(7) 0.0686(4) Uani 1 1 d . . . S2 S 1.27116(16) 0.61986(5) 0.32588(7) 0.0737(4) Uani 1 1 d . . . N1U N 1.2214(3) 0.73770(15) 0.36092(17) 0.0386(9) Uani 1 1 d . . . H1U H 1.2615 0.7443 0.3142 0.058 Uiso 1 1 calc R . . N2U N 1.1080(4) 0.77532(16) 0.4750(2) 0.0490(10) Uani 1 1 d . . . H2U H 1.0708 0.8052 0.5034 0.074 Uiso 1 1 calc R . . C1U C 1.1773(5) 0.78905(19) 0.4037(3) 0.0421(11) Uani 1 1 d . . . C2U C 1.2088(5) 0.67663(18) 0.3840(2) 0.0413(11) Uani 1 1 d . . . C3U C 1.1426(5) 0.66778(19) 0.4612(2) 0.0487(12) Uani 1 1 d . . . H3U H 1.1325 0.6281 0.4822 0.058 Uiso 1 1 calc R . . C4U C 1.0942(5) 0.7170(2) 0.5039(2) 0.0537(13) Uani 1 1 d . . . H4U H 1.0503 0.7109 0.5545 0.064 Uiso 1 1 calc R . . O1 O 0.7365(3) 0.77925(12) 0.52398(16) 0.0549(8) Uani 1 1 d . . . C2 C 0.5984(5) 0.74244(19) 0.4939(3) 0.0736(15) Uani 1 1 d . . . H2A H 0.5527 0.7592 0.4427 0.088 Uiso 1 1 calc R . . H2B H 0.5108 0.7430 0.5325 0.088 Uiso 1 1 calc R . . C3 C 0.6556(5) 0.6785(2) 0.4819(3) 0.0718(15) Uani 1 1 d . . . H3A H 0.5626 0.6534 0.4605 0.086 Uiso 1 1 calc R . . H3B H 0.7420 0.6780 0.4427 0.086 Uiso 1 1 calc R . . O4 O 0.7198(3) 0.65351(13) 0.55645(17) 0.0543(8) Uani 1 1 d . . . C5 C 0.7568(5) 0.58988(19) 0.5493(3) 0.0665(14) Uani 1 1 d . . . H5A H 0.8323 0.5836 0.5058 0.080 Uiso 1 1 calc R . . H5B H 0.6546 0.5669 0.5361 0.080 Uiso 1 1 calc R . . C6 C 0.8360(5) 0.56736(18) 0.6274(3) 0.0661(14) Uani 1 1 d . . . H6A H 0.7714 0.5809 0.6723 0.079 Uiso 1 1 calc R . . H6B H 0.8392 0.5225 0.6276 0.079 Uiso 1 1 calc R . . O7 O 1.0016(3) 0.59138(11) 0.63646(16) 0.0491(8) Uani 1 1 d . . . C8 C 1.0809(5) 0.57852(18) 0.7143(2) 0.0468(11) Uani 1 1 d . . . H8A H 1.0094 0.5933 0.7568 0.056 Uiso 1 1 calc R . . C9 C 1.2434(5) 0.6138(2) 0.7195(2) 0.0535(13) Uani 1 1 d . . . H9A H 1.2960 0.6079 0.7742 0.064 Uiso 1 1 calc R . . O10 O 1.2067(3) 0.67844(13) 0.70911(15) 0.0545(8) Uani 1 1 d . . . C11 C 1.3416(6) 0.7176(2) 0.7382(3) 0.0877(17) Uani 1 1 d . . . H11A H 1.4392 0.7101 0.7071 0.105 Uiso 1 1 calc R . . H11B H 1.3713 0.7082 0.7949 0.105 Uiso 1 1 calc R . . C12 C 1.2912(6) 0.7833(2) 0.7304(3) 0.0803(16) Uani 1 1 d . . . H12A H 1.1851 0.7894 0.7552 0.096 Uiso 1 1 calc R . . H12B H 1.3747 0.8091 0.7588 0.096 Uiso 1 1 calc R . . O13 O 1.2753(3) 0.80052(13) 0.64780(17) 0.0547(8) Uani 1 1 d . . . C14 C 1.2542(5) 0.86536(19) 0.6348(3) 0.0703(14) Uani 1 1 d . . . H14A H 1.2861 0.8751 0.5802 0.084 Uiso 1 1 calc R . . H14B H 1.3306 0.8872 0.6727 0.084 Uiso 1 1 calc R . . C15 C 1.0846(5) 0.88860(18) 0.6443(3) 0.0690(14) Uani 1 1 d . . . H15A H 1.0467 0.8760 0.6969 0.083 Uiso 1 1 calc R . . H15B H 1.0849 0.9334 0.6424 0.083 Uiso 1 1 calc R . . O16 O 0.9727(3) 0.86511(11) 0.58110(14) 0.0470(7) Uani 1 1 d . . . C17 C 0.7999(5) 0.87117(18) 0.5998(2) 0.0461(11) Uani 1 1 d . . . H17A H 0.7802 0.8487 0.6501 0.055 Uiso 1 1 calc R . . C18 C 0.6947(5) 0.84350(18) 0.5302(3) 0.0451(12) Uani 1 1 d . . . H18A H 0.5772 0.8461 0.5440 0.054 Uiso 1 1 calc R . . C19 C 0.7113(5) 0.87801(19) 0.4514(2) 0.0612(13) Uani 1 1 d . . . H19A H 0.6371 0.8599 0.4092 0.073 Uiso 1 1 calc R . . H19B H 0.8254 0.8745 0.4346 0.073 Uiso 1 1 calc R . . C20 C 0.6674(6) 0.9456(2) 0.4621(3) 0.0915(18) Uani 1 1 d . . . H20A H 0.5494 0.9491 0.4725 0.110 Uiso 1 1 calc R . . H20B H 0.6864 0.9678 0.4122 0.110 Uiso 1 1 calc R . . C21 C 0.7716(6) 0.97474(19) 0.5322(3) 0.0796(16) Uani 1 1 d . . . H21A H 0.8889 0.9750 0.5197 0.096 Uiso 1 1 calc R . . H21B H 0.7363 1.0172 0.5396 0.096 Uiso 1 1 calc R . . C22 C 0.7503(5) 0.93876(19) 0.6092(3) 0.0621(14) Uani 1 1 d . . . H22A H 0.6342 0.9410 0.6234 0.074 Uiso 1 1 calc R . . H22B H 0.8189 0.9572 0.6533 0.074 Uiso 1 1 calc R . . C23 C 1.3645(5) 0.59062(18) 0.6579(2) 0.0646(13) Uani 1 1 d . . . H23A H 1.4693 0.6131 0.6646 0.077 Uiso 1 1 calc R . . H23B H 1.3174 0.5980 0.6031 0.077 Uiso 1 1 calc R . . C24 C 1.3974(6) 0.5213(2) 0.6699(3) 0.0828(16) Uani 1 1 d . . . H24A H 1.4560 0.5145 0.7224 0.099 Uiso 1 1 calc R . . H24B H 1.4683 0.5065 0.6280 0.099 Uiso 1 1 calc R . . C25 C 1.2320(6) 0.48500(19) 0.6658(3) 0.0778(15) Uani 1 1 d . . . H25A H 1.1790 0.4884 0.6114 0.093 Uiso 1 1 calc R . . H25B H 1.2550 0.4416 0.6765 0.093 Uiso 1 1 calc R . . C26 C 1.1149(5) 0.50923(18) 0.7270(2) 0.0662(14) Uani 1 1 d . . . H26A H 1.1639 0.5025 0.7816 0.079 Uiso 1 1 calc R . . H26B H 1.0099 0.4867 0.7217 0.079 Uiso 1 1 calc R . . O1W O 1.3612(4) 0.76812(14) 0.20607(17) 0.0656(9) Uani 1 1 d D . . H1W H 1.446(3) 0.7892(17) 0.216(2) 0.098 Uiso 1 1 d D . . H2W H 1.297(4) 0.7730(19) 0.1649(18) 0.098 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 S1 0.0791(10) 0.0491(8) 0.0790(9) -0.0068(7) 0.0161(8) -0.0105(7) S2 0.1112(12) 0.0528(8) 0.0593(8) -0.0119(7) 0.0254(8) 0.0049(8) N1U 0.037(2) 0.051(2) 0.029(2) -0.0051(19) 0.0085(17) -0.0054(19) N2U 0.046(2) 0.060(3) 0.043(2) -0.014(2) 0.012(2) 0.007(2) C1U 0.032(3) 0.057(3) 0.037(3) -0.013(3) 0.001(2) 0.001(2) C2U 0.039(3) 0.045(3) 0.040(3) 0.000(2) 0.000(2) -0.004(2) C3U 0.062(3) 0.046(3) 0.039(3) 0.006(2) 0.014(3) -0.003(2) C4U 0.048(3) 0.080(4) 0.033(3) 0.006(3) 0.009(2) -0.001(3) O1 0.0417(19) 0.0393(18) 0.082(2) -0.0082(17) -0.0127(16) -0.0021(16) C2 0.057(3) 0.057(3) 0.102(4) -0.002(3) -0.032(3) 0.002(3) C3 0.061(3) 0.063(4) 0.087(4) -0.008(3) -0.027(3) -0.013(3) O4 0.053(2) 0.050(2) 0.058(2) 0.0036(17) -0.0113(17) -0.0048(17) C5 0.055(3) 0.048(3) 0.096(4) -0.009(3) -0.005(3) -0.014(3) C6 0.056(4) 0.050(3) 0.091(4) 0.009(3) -0.008(3) -0.002(3) O7 0.0362(19) 0.0544(19) 0.056(2) 0.0101(16) -0.0021(16) -0.0060(16) C8 0.048(3) 0.046(3) 0.047(3) 0.003(2) 0.013(3) -0.003(3) C9 0.060(4) 0.055(3) 0.044(3) 0.017(3) -0.002(3) 0.012(3) O10 0.045(2) 0.046(2) 0.071(2) 0.0049(17) -0.0114(16) -0.0016(17) C11 0.081(4) 0.058(4) 0.118(5) 0.022(3) -0.045(3) -0.011(3) C12 0.088(4) 0.077(4) 0.071(4) -0.003(3) -0.032(3) -0.025(3) O13 0.056(2) 0.0428(19) 0.064(2) -0.0048(17) -0.0128(17) -0.0015(16) C14 0.049(3) 0.055(3) 0.106(4) -0.017(3) -0.005(3) -0.016(3) C15 0.046(3) 0.056(3) 0.104(4) -0.027(3) -0.002(3) -0.001(3) O16 0.0366(18) 0.0478(18) 0.0561(19) -0.0093(16) -0.0037(16) 0.0021(16) C17 0.049(3) 0.050(3) 0.040(3) 0.002(2) 0.009(2) 0.004(3) C18 0.027(3) 0.054(3) 0.056(3) 0.001(3) 0.011(2) 0.004(2) C19 0.057(3) 0.081(4) 0.046(3) 0.009(3) -0.001(2) 0.006(3) C20 0.105(5) 0.065(4) 0.105(5) 0.031(3) 0.004(4) 0.025(3) C21 0.087(4) 0.041(3) 0.110(5) 0.004(3) -0.002(4) 0.010(3) C22 0.050(3) 0.062(3) 0.075(4) -0.015(3) 0.013(3) 0.011(3) C23 0.051(3) 0.066(4) 0.077(4) 0.015(3) 0.012(3) 0.005(3) C24 0.080(4) 0.078(4) 0.093(4) 0.005(3) 0.027(3) 0.035(3) C25 0.106(5) 0.047(3) 0.081(4) 0.004(3) 0.018(4) 0.018(3) C26 0.093(4) 0.050(3) 0.056(3) 0.012(3) 0.008(3) -0.002(3) O1W 0.074(3) 0.075(2) 0.049(2) 0.002(2) 0.0070(18) -0.018(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 S1 C1U 1.642(4) . ? S2 C2U 1.649(4) . ? N1U C1U 1.371(4) . ? N1U C2U 1.379(4) . ? N1U H1U 0.8600 . ? N2U C4U 1.355(4) . ? N2U C1U 1.357(4) . ? N2U H2U 0.8600 . ? C2U C3U 1.414(4) . ? C3U C4U 1.344(4) . ? C3U H3U 0.9300 . ? C4U H4U 0.9300 . ? O1 C2 1.427(4) . ? O1 C18 1.434(4) . ? C2 C3 1.473(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O4 1.409(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C5 1.414(4) . ? C5 C6 1.482(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O7 1.422(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O7 C8 1.424(4) . ? C8 C9 1.504(5) . ? C8 C26 1.535(4) . ? C8 H8A 0.9800 . ? C9 O10 1.436(4) . ? C9 C23 1.523(5) . ? C9 H9A 0.9800 . ? O10 C11 1.432(4) . ? C11 C12 1.480(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O13 1.407(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O13 C14 1.427(4) . ? C14 C15 1.462(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 O16 1.426(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? O16 C17 1.437(4) . ? C17 C18 1.505(4) . ? C17 C22 1.525(5) . ? C17 H17A 0.9800 . ? C18 C19 1.506(4) . ? C18 H18A 0.9800 . ? C19 C20 1.515(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.521(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.503(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.532(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.535(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.506(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? O1W H1W 0.826(17) . ? O1W H2W 0.832(17) . ? 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 C1U N1U C2U 127.6(3) . . ? C1U N1U H1U 116.2 . . ? C2U N1U H1U 116.2 . . ? C4U N2U C1U 123.5(4) . . ? C4U N2U H2U 118.3 . . ? C1U N2U H2U 118.3 . . ? N2U C1U N1U 113.2(3) . . ? N2U C1U S1 122.8(3) . . ? N1U C1U S1 124.0(3) . . ? N1U C2U C3U 114.4(3) . . ? N1U C2U S2 121.6(3) . . ? C3U C2U S2 124.0(3) . . ? C4U C3U C2U 119.6(4) . . ? C4U C3U H3U 120.2 . . ? C2U C3U H3U 120.2 . . ? C3U C4U N2U 121.5(4) . . ? C3U C4U H4U 119.2 . . ? N2U C4U H4U 119.2 . . ? C2 O1 C18 112.7(3) . . ? O1 C2 C3 109.3(3) . . ? O1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? O1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? O4 C3 C2 110.1(4) . . ? O4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C3 O4 C5 111.6(3) . . ? O4 C5 C6 109.2(4) . . ? O4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? O4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? O7 C6 C5 108.7(3) . . ? O7 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? O7 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C6 O7 C8 112.8(3) . . ? O7 C8 C9 106.9(3) . . ? O7 C8 C26 112.3(3) . . ? C9 C8 C26 110.0(4) . . ? O7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C26 C8 H8A 109.2 . . ? O10 C9 C8 108.5(3) . . ? O10 C9 C23 112.0(3) . . ? C8 C9 C23 111.9(4) . . ? O10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C23 C9 H9A 108.1 . . ? C11 O10 C9 113.0(3) . . ? O10 C11 C12 110.0(4) . . ? O10 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? O10 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O13 C12 C11 110.4(4) . . ? O13 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? O13 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C12 O13 C14 114.1(3) . . ? O13 C14 C15 115.1(3) . . ? O13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? O13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? O16 C15 C14 110.3(3) . . ? O16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? O16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 O16 C17 112.5(3) . . ? O16 C17 C18 107.7(3) . . ? O16 C17 C22 111.6(3) . . ? C18 C17 C22 108.7(3) . . ? O16 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? C22 C17 H17A 109.6 . . ? O1 C18 C19 112.8(3) . . ? O1 C18 C17 108.5(3) . . ? C19 C18 C17 112.6(3) . . ? O1 C18 H18A 107.6 . . ? C19 C18 H18A 107.6 . . ? C17 C18 H18A 107.6 . . ? C18 C19 C20 110.3(3) . . ? C18 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? C18 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C19 C20 C21 111.5(4) . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C20 109.9(4) . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C21 C22 C17 111.6(3) . . ? C21 C22 H22A 109.3 . . ? C17 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? C17 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C9 C23 C24 110.3(3) . . ? C9 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C9 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C25 110.7(4) . . ? C23 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C26 C25 C24 110.9(4) . . ? C26 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C8 111.2(3) . . ? C25 C26 H26A 109.4 . . ? C8 C26 H26A 109.4 . . ? C25 C26 H26B 109.4 . . ? C8 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? H1W O1W H2W 124(3) . . ? 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 C2 C3 O4 60.4(5) . . . . ? C2 C3 O4 C5 172.8(3) . . . . ? C3 O4 C5 C6 175.6(3) . . . . ? O4 C5 C6 O7 -72.3(4) . . . . ? C5 C6 O7 C8 172.8(3) . . . . ? C6 O7 C8 C9 -172.2(3) . . . . ? O7 C8 C9 O10 59.0(4) . . . . ? C8 C9 O10 C11 161.1(3) . . . . ? C9 O10 C11 C12 -176.4(4) . . . . ? O10 C11 C12 O13 -69.3(5) . . . . ? C11 C12 O13 C14 -170.2(3) . . . . ? C12 O13 C14 C15 -79.5(5) . . . . ? O13 C14 C15 O16 -67.6(5) . . . . ? C14 C15 O16 C17 163.1(3) . . . . ? C15 O16 C17 C18 -178.5(3) . . . . ? O16 C17 C18 O1 61.6(4) . . . . ? C17 C18 O1 C2 149.1(3) . . . . ? C18 O1 C2 C3 174.6(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 N2U H2U O16 0.86 2.01 2.862(4) 171.3 . N1U H1U O1W 0.86 2.05 2.911(4) 174.9 . O1W H2W O1 0.832(17) 2.60(3) 3.267(4) 138(4) 4_675 O1W H2W O4 0.832(17) 2.44(3) 3.145(4) 143(3) 4_675 O1W H1W O10 0.826(17) 2.21(2) 2.990(4) 159(4) 4_675 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.172 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.043 data_dtu8 _database_code_depnum_ccdc_archive 'CCDC 268387' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2-ene pyrimidine-2,4(1H,3H)-dithione monohydrate ; _chemical_name_common ; 2,3-benzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2-ene pyrimidine-2,4(1H,3H)-dithione monohydrate ; _chemical_melting_point >250(decomp) _chemical_formula_moiety 'C16 H24 O6, C4 H4 N2 S2, H2 O' _chemical_formula_sum 'C20 H30 N2 O7 S2' _chemical_formula_weight 474.58 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.9730(16) _cell_length_b 16.918(3) _cell_length_c 17.566(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2369.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 5.37 _cell_measurement_theta_max 15.30 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Philips Pw1100' _diffrn_measurement_method 'omega-2theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2644 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2644 _reflns_number_gt 1493 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0417P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.22(13) _refine_ls_number_reflns 2644 _refine_ls_number_parameters 292 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 S1 S -0.5897(2) -0.35452(6) 0.16174(7) 0.0721(4) Uani 1 1 d . . . S2 S -0.61006(19) -0.66532(6) 0.18934(7) 0.0647(4) Uani 1 1 d . . . N1U N -0.6005(5) -0.51152(19) 0.16074(17) 0.0395(8) Uani 1 1 d D . . H1U H -0.634(5) -0.507(2) 0.2064(13) 0.059 Uiso 1 1 d D . . N2U N -0.5290(5) -0.4540(2) 0.0475(2) 0.0570(11) Uani 1 1 d D . . H2U H -0.522(6) -0.4119(18) 0.020(2) 0.085 Uiso 1 1 d D . . C1U C -0.5738(6) -0.4435(2) 0.1224(2) 0.0448(12) Uani 1 1 d . . . C2U C -0.5787(5) -0.5879(2) 0.1340(2) 0.0402(11) Uani 1 1 d . . . C3U C -0.5303(5) -0.5919(3) 0.0568(2) 0.0505(12) Uani 1 1 d . . . H3U H -0.5135 -0.6410 0.0343 0.061 Uiso 1 1 calc R . . C4U C -0.5086(5) -0.5270(3) 0.0161(2) 0.0541(13) Uani 1 1 d . . . H4U H -0.4788 -0.5313 -0.0349 0.065 Uiso 1 1 calc R . . O1 O -0.8743(3) -0.59234(15) -0.04749(14) 0.0449(7) Uani 1 1 d . . . C2 C -0.8676(6) -0.6767(2) -0.0554(2) 0.0495(12) Uani 1 1 d . . . H2A H -0.9802 -0.6981 -0.0591 0.059 Uiso 1 1 calc R . . H2B H -0.8133 -0.7000 -0.0113 0.059 Uiso 1 1 calc R . . C3 C -0.7713(6) -0.6957(3) -0.1254(2) 0.0520(12) Uani 1 1 d . . . H3A H -0.7800 -0.7518 -0.1365 0.062 Uiso 1 1 calc R . . H3B H -0.8167 -0.6666 -0.1683 0.062 Uiso 1 1 calc R . . O4 O -0.6019(4) -0.67493(16) -0.11417(16) 0.0536(8) Uani 1 1 d . . . C5 C -0.5036(6) -0.6868(2) -0.1813(3) 0.0610(14) Uani 1 1 d . . . H5A H -0.5590 -0.6630 -0.2247 0.073 Uiso 1 1 calc R . . H5B H -0.4913 -0.7430 -0.1911 0.073 Uiso 1 1 calc R . . C6 C -0.3376(6) -0.6507(3) -0.1703(3) 0.0620(13) Uani 1 1 d . . . H6A H -0.2896 -0.6686 -0.1226 0.074 Uiso 1 1 calc R . . H6B H -0.2633 -0.6665 -0.2113 0.074 Uiso 1 1 calc R . . O7 O -0.3541(4) -0.56711(16) -0.16941(15) 0.0518(8) Uani 1 1 d . . . C8 C -0.1959(6) -0.5293(3) -0.1606(3) 0.0659(15) Uani 1 1 d . . . H8A H -0.1193 -0.5480 -0.1995 0.079 Uiso 1 1 calc R . . H8B H -0.1489 -0.5427 -0.1113 0.079 Uiso 1 1 calc R . . C9 C -0.2151(8) -0.4424(3) -0.1667(2) 0.0713(16) Uani 1 1 d . . . H9A H -0.1060 -0.4184 -0.1749 0.086 Uiso 1 1 calc R . . H9B H -0.2853 -0.4299 -0.2102 0.086 Uiso 1 1 calc R . . O10 O -0.2868(4) -0.4111(2) -0.10094(19) 0.0749(10) Uani 1 1 d . . . C11 C -0.3191(7) -0.3281(3) -0.1070(4) 0.090(2) Uani 1 1 d . . . H11A H -0.2425 -0.3053 -0.1439 0.108 Uiso 1 1 calc R . . H11B H -0.2976 -0.3033 -0.0582 0.108 Uiso 1 1 calc R . . C12 C -0.4963(7) -0.3108(3) -0.1309(3) 0.0759(18) Uani 1 1 d . . . H12A H -0.5100 -0.2546 -0.1401 0.091 Uiso 1 1 calc R . . H12B H -0.5228 -0.3390 -0.1775 0.091 Uiso 1 1 calc R . . O13 O -0.6035(4) -0.33515(16) -0.07223(16) 0.0562(8) Uani 1 1 d . . . C14 C -0.7774(6) -0.3226(3) -0.0903(3) 0.0593(14) Uani 1 1 d . . . H14A H -0.8045 -0.3481 -0.1382 0.071 Uiso 1 1 calc R . . H14B H -0.7995 -0.2664 -0.0954 0.071 Uiso 1 1 calc R . . C15 C -0.8817(7) -0.3562(2) -0.0284(3) 0.0595(13) Uani 1 1 d . . . H15A H -0.8371 -0.3404 0.0207 0.071 Uiso 1 1 calc R . . H15B H -0.9957 -0.3366 -0.0324 0.071 Uiso 1 1 calc R . . O16 O -0.8804(4) -0.44034(15) -0.03475(16) 0.0507(8) Uani 1 1 d . . . C17 C -0.9611(5) -0.4820(3) 0.0224(2) 0.0460(11) Uani 1 1 d . . . C18 C -0.9566(5) -0.5636(3) 0.0157(2) 0.0440(11) Uani 1 1 d . . . C19 C -1.0347(6) -0.6099(3) 0.0696(3) 0.0597(14) Uani 1 1 d . . . H19 H -1.0335 -0.6646 0.0646 0.072 Uiso 1 1 calc R . . C20 C -1.1140(7) -0.5761(3) 0.1306(3) 0.0753(16) Uani 1 1 d . . . H20 H -1.1657 -0.6078 0.1670 0.090 Uiso 1 1 calc R . . C21 C -1.1168(7) -0.4972(4) 0.1377(3) 0.0745(16) Uani 1 1 d . . . H21 H -1.1701 -0.4748 0.1796 0.089 Uiso 1 1 calc R . . C22 C -1.0415(7) -0.4475(3) 0.0836(3) 0.0662(15) Uani 1 1 d . . . H22 H -1.0455 -0.3928 0.0888 0.079 Uiso 1 1 calc R . . O1W O -0.7771(4) -0.4995(2) 0.30943(17) 0.0637(9) Uani 1 1 d D . . H1W H -0.882(2) -0.489(3) 0.309(2) 0.095 Uiso 1 1 d D . . H2W H -0.727(5) -0.490(3) 0.3516(18) 0.095 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 S1 0.1112(12) 0.0387(6) 0.0664(8) 0.0042(6) 0.0052(10) 0.0033(8) S2 0.0873(10) 0.0382(6) 0.0686(8) 0.0004(6) 0.0112(9) -0.0041(8) N1U 0.051(2) 0.0394(18) 0.0276(18) -0.0013(18) 0.000(2) 0.001(2) N2U 0.068(3) 0.061(3) 0.042(2) 0.016(2) 0.002(2) 0.004(2) C1U 0.052(3) 0.047(3) 0.035(2) 0.010(2) -0.004(2) -0.001(3) C2U 0.036(3) 0.049(3) 0.036(2) -0.0053(19) 0.000(2) 0.003(2) C3U 0.055(3) 0.051(3) 0.045(3) -0.010(2) -0.005(3) 0.003(3) C4U 0.056(3) 0.068(3) 0.039(3) -0.014(3) -0.003(2) 0.012(3) O1 0.0487(19) 0.0441(16) 0.0420(15) -0.0051(13) 0.0079(17) 0.0036(16) C2 0.053(3) 0.042(3) 0.053(3) 0.002(2) 0.003(3) -0.002(3) C3 0.063(3) 0.037(3) 0.057(3) -0.005(2) 0.000(3) -0.007(3) O4 0.053(2) 0.0532(18) 0.0546(18) -0.0115(15) 0.0099(18) -0.0038(19) C5 0.074(4) 0.039(3) 0.070(3) -0.012(3) 0.020(3) 0.004(3) C6 0.062(3) 0.052(3) 0.072(3) 0.004(3) 0.018(3) 0.013(3) O7 0.0450(19) 0.0491(17) 0.0613(19) 0.0047(16) 0.0009(17) 0.0038(16) C8 0.038(3) 0.101(4) 0.059(3) -0.017(3) 0.002(3) 0.003(3) C9 0.103(4) 0.070(4) 0.041(3) -0.008(3) 0.010(3) -0.038(3) O10 0.077(3) 0.064(2) 0.084(2) 0.012(2) 0.013(2) 0.000(2) C11 0.085(5) 0.054(4) 0.132(5) 0.018(4) 0.012(4) -0.011(3) C12 0.097(5) 0.042(3) 0.089(4) 0.025(3) -0.008(4) -0.007(3) O13 0.063(2) 0.0519(18) 0.0540(18) 0.0140(15) 0.0019(19) -0.001(2) C14 0.076(4) 0.040(3) 0.062(3) 0.006(2) -0.019(3) 0.012(3) C15 0.059(3) 0.057(3) 0.062(3) -0.007(2) -0.008(3) 0.013(3) O16 0.058(2) 0.0416(17) 0.0522(17) -0.0096(15) 0.0010(19) 0.0003(17) C17 0.041(3) 0.065(3) 0.032(2) -0.007(2) 0.001(2) -0.001(3) C18 0.038(3) 0.055(3) 0.039(2) -0.004(2) -0.002(2) 0.001(2) C19 0.057(3) 0.076(3) 0.047(3) 0.003(3) 0.007(3) -0.007(3) C20 0.084(4) 0.089(4) 0.052(3) -0.004(3) 0.022(3) -0.023(4) C21 0.074(4) 0.107(5) 0.043(3) -0.013(3) 0.023(3) -0.009(4) C22 0.073(4) 0.066(3) 0.060(3) -0.019(3) 0.003(3) 0.000(3) O1W 0.072(2) 0.066(2) 0.052(2) -0.0001(18) 0.0029(19) 0.011(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 S1 C1U 1.662(4) . ? S2 C2U 1.651(4) . ? N1U C1U 1.350(5) . ? N1U C2U 1.385(5) . ? N1U H1U 0.850(19) . ? N2U C4U 1.361(5) . ? N2U C1U 1.375(5) . ? N2U H2U 0.857(19) . ? C2U C3U 1.411(5) . ? C3U C4U 1.322(6) . ? C3U H3U 0.9300 . ? C4U H4U 0.9300 . ? O1 C18 1.377(4) . ? O1 C2 1.435(4) . ? C2 C3 1.486(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O4 1.409(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C5 1.430(5) . ? C5 C6 1.470(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O7 1.420(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O7 C8 1.422(5) . ? C8 C9 1.483(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O10 1.393(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? O10 C11 1.431(6) . ? C11 C12 1.503(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O13 1.401(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? O13 C14 1.438(5) . ? C14 C15 1.483(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 O16 1.429(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? O16 C17 1.385(5) . ? C17 C22 1.381(6) . ? C17 C18 1.385(6) . ? C18 C19 1.379(6) . ? C19 C20 1.369(6) . ? C19 H19 0.9300 . ? C20 C21 1.341(7) . ? C20 H20 0.9300 . ? C21 C22 1.404(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? O1W H1W 0.858(14) . ? O1W H2W 0.855(18) . ? 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 C1U N1U C2U 127.2(3) . . ? C1U N1U H1U 116(3) . . ? C2U N1U H1U 117(3) . . ? C4U N2U C1U 122.3(4) . . ? C4U N2U H2U 121(3) . . ? C1U N2U H2U 116(3) . . ? N1U C1U N2U 114.1(4) . . ? N1U C1U S1 123.5(3) . . ? N2U C1U S1 122.4(3) . . ? N1U C2U C3U 113.9(4) . . ? N1U C2U S2 121.4(3) . . ? C3U C2U S2 124.6(3) . . ? C4U C3U C2U 121.0(4) . . ? C4U C3U H3U 119.5 . . ? C2U C3U H3U 119.5 . . ? C3U C4U N2U 121.3(4) . . ? C3U C4U H4U 119.3 . . ? N2U C4U H4U 119.3 . . ? C18 O1 C2 116.5(3) . . ? O1 C2 C3 108.3(3) . . ? O1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? O1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? O4 C3 C2 109.0(4) . . ? O4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? O4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C3 O4 C5 112.0(3) . . ? O4 C5 C6 109.1(4) . . ? O4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? O4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? O7 C6 C5 109.4(4) . . ? O7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? O7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C6 O7 C8 111.5(3) . . ? O7 C8 C9 110.3(4) . . ? O7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? O7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O10 C9 C8 111.0(4) . . ? O10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 O10 C11 112.6(4) . . ? O10 C11 C12 112.4(4) . . ? O10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? O10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? O13 C12 C11 108.1(4) . . ? O13 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? O13 C12 H12B 110.1 . . ? C11 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C12 O13 C14 112.4(4) . . ? O13 C14 C15 108.8(4) . . ? O13 C14 H14A 109.9 . . ? C15 C14 H14A 109.9 . . ? O13 C14 H14B 109.9 . . ? C15 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O16 C15 C14 108.7(4) . . ? O16 C15 H15A 110.0 . . ? C14 C15 H15A 110.0 . . ? O16 C15 H15B 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.3 . . ? C17 O16 C15 116.6(3) . . ? C22 C17 C18 120.0(4) . . ? C22 C17 O16 124.3(4) . . ? C18 C17 O16 115.7(4) . . ? O1 C18 C19 124.6(4) . . ? O1 C18 C17 115.7(4) . . ? C19 C18 C17 119.7(4) . . ? C20 C19 C18 120.6(5) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C21 C20 C19 119.8(5) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 121.7(5) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C17 C22 C21 118.2(5) . . ? C17 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? H1W O1W H2W 115(3) . . ? 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 C2 C3 O4 68.5(4) . . . . ? C2 C3 O4 C5 -176.2(3) . . . . ? C3 O4 C5 C6 169.6(4) . . . . ? O4 C5 C6 O7 -69.7(5) . . . . ? C5 C6 O7 C8 -178.7(4) . . . . ? C6 O7 C8 C9 175.0(4) . . . . ? O7 C8 C9 O10 75.0(5) . . . . ? C8 C9 O10 C11 -175.5(4) . . . . ? C9 O10 C11 C12 95.5(6) . . . . ? O10 C11 C12 O13 66.3(6) . . . . ? C11 C12 O13 C14 -178.7(4) . . . . ? C12 O13 C14 C15 175.2(4) . . . . ? O13 C14 C15 O16 -74.5(5) . . . . ? C14 C15 O16 C17 175.0(4) . . . . ? C15 O16 C17 C18 -179.2(4) . . . . ? O16 C17 C18 O1 -0.8(6) . . . . ? C17 C18 O1 C2 179.8(4) . . . . ? C18 O1 C2 C3 -178.8(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 N1U H1U O1W 0.850(19) 2.14(2) 2.974(4) 166(4) . N2U H2U O13 0.857(19) 2.18(3) 2.970(4) 153(4) . C4U H4U O7 0.93 2.63 3.550(5) 168.2 . O1W H2W O1 0.855(18) 2.40(3) 3.191(4) 155(5) 2_345 O1W H2W O16 0.855(18) 2.47(4) 3.179(4) 141(5) 2_345 O1W H1W O7 0.858(14) 2.337(16) 3.171(4) 164(4) 2_345 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.299 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.039