Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Packianathan Thomas Muthiah' 'Gabriele Bocelli' 'Andrea Cantoni' 'S. Francis' 'Madhukar Hemamalini' ; S.B.Raj ; 'Urszula Rychlewska' 'V. Sethuraman' 'B. Warzajtis' _publ_contact_author_name 'Dr Packianathan Thomas Muthiah' _publ_contact_author_address ; Department of Chemistry Bharathidasan University Tiruchirappalli-620024 Tamilnadu, India ; _publ_contact_author_email tommtrichy@yahoo.co.in _publ_contact_author_fax 0431-407045 _publ_contact_author_phone 0431-407053 #============================================================================ # 3. TITLE AND AUTHOR LIST _publ_section_title ; Supramolecular organisation via hydrogen bonding in trimethoprim sulphonate salts ; data_for_compound_3 _database_code_CSD 192069 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [2,4-diamino-5-(3',4',5'-trimethoxybenzyl pyrimidinium)] 4-methylbenzene sulfonate ; _chemical_name_common 'Trimethoprim p-toluenesulfonate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 N4 O6 S' _chemical_formula_weight 462.52 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 13.407(3) _cell_length_b 10.039(3) _cell_length_c 17.115(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.60(3) _cell_angle_gamma 90.00 _cell_volume 2303.4(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.185 _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 'CAD-4 Enraf Nonius' _diffrn_measurement_method '\w-2 scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4216 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4031 _reflns_number_gt 2868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Enraf-Nonius' _computing_cell_refinement 'CAD4 Enraf-Nonius' _computing_data_reduction 'CAD4 Enraf-Nonius' _computing_structure_solution ? _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^)+(0.0564P)^2^+0.8259P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0171(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4031 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 C2 C 0.61380(15) 0.5647(2) 0.34279(11) 0.0397(5) Uani 1 1 d . . . C4 C 0.50119(15) 0.6756(2) 0.41966(11) 0.0403(5) Uani 1 1 d . . . C5 C 0.49299(15) 0.7835(2) 0.36473(11) 0.0386(5) Uani 1 1 d . . . C6 C 0.55281(16) 0.7728(2) 0.30261(12) 0.0412(5) Uani 1 1 d . . . C7 C 0.4228(2) 0.9003(3) 0.37712(14) 0.0541(6) Uani 1 1 d . . . C8 C 0.38962(18) 0.9670(2) 0.30153(13) 0.0498(6) Uani 1 1 d . . . C9 C 0.4538(2) 1.0514(2) 0.26208(14) 0.0526(6) Uani 1 1 d . . . C10 C 0.42418(18) 1.1065(2) 0.19078(14) 0.0534(6) Uani 1 1 d . . . C11 C 0.33042(19) 1.0804(2) 0.16074(15) 0.0592(6) Uani 1 1 d . . . C12 C 0.26628(19) 0.9966(3) 0.20086(16) 0.0633(7) Uani 1 1 d . . . C13 C 0.2966(2) 0.9401(3) 0.27124(16) 0.0592(7) Uani 1 1 d . . . C14 C 0.5830(2) 1.2047(4) 0.1683(2) 0.0993(11) Uani 1 1 d . . . H14A H 0.6145 1.2653 0.1329 0.149 Uiso 1 1 calc R . . H14B H 0.6158 1.1197 0.1660 0.149 Uiso 1 1 calc R . . H14C H 0.5879 1.2392 0.2205 0.149 Uiso 1 1 calc R . . C15 C 0.3152(4) 1.0651(4) 0.0249(2) 0.1258(16) Uani 1 1 d . . . H15A H 0.2794 0.9826 0.0288 0.189 Uiso 1 1 calc R . . H15B H 0.3852 1.0471 0.0198 0.189 Uiso 1 1 calc R . . H15C H 0.2919 1.1136 -0.0201 0.189 Uiso 1 1 calc R . . C16 C 0.1160(2) 0.8697(4) 0.1946(2) 0.1027(12) Uani 1 1 d . . . H16A H 0.0548 0.8646 0.1652 0.154 Uiso 1 1 calc R . . H16B H 0.1016 0.8858 0.2486 0.154 Uiso 1 1 calc R . . H16C H 0.1516 0.7872 0.1898 0.154 Uiso 1 1 calc R . . C17 C 0.72178(16) 0.5178(2) 0.04547(12) 0.0438(5) Uani 1 1 d . . . C18 C 0.6452(2) 0.5745(3) 0.00409(16) 0.0669(7) Uani 1 1 d . . . C19 C 0.6051(3) 0.5087(3) -0.06023(19) 0.0802(9) Uani 1 1 d . . . C20 C 0.6400(2) 0.3863(3) -0.08243(16) 0.0690(7) Uani 1 1 d . . . C21 C 0.7179(3) 0.3327(3) -0.04154(18) 0.0757(8) Uani 1 1 d . . . C22 C 0.7597(2) 0.3970(3) 0.02226(16) 0.0646(7) Uani 1 1 d . . . C23 C 0.5926(3) 0.3147(4) -0.1514(2) 0.1095(12) Uani 1 1 d . . . H23A H 0.5391 0.3678 -0.1724 0.164 Uiso 1 1 calc R . . H23B H 0.5669 0.2303 -0.1345 0.164 Uiso 1 1 calc R . . H23C H 0.6418 0.3006 -0.1909 0.164 Uiso 1 1 calc R . . N1 N 0.61384(13) 0.66705(17) 0.29197(10) 0.0414(4) Uani 1 1 d . . . N2 N 0.67049(18) 0.4602(2) 0.32754(13) 0.0585(6) Uani 1 1 d . . . N3 N 0.55833(13) 0.56767(17) 0.40670(9) 0.0435(4) Uani 1 1 d . . . N4 N 0.45282(17) 0.6777(2) 0.48664(11) 0.0562(6) Uani 1 1 d . . . O1 O 0.48226(14) 1.18971(18) 0.14721(11) 0.0730(6) Uani 1 1 d . . . O2 O 0.29946(15) 1.1411(2) 0.09223(12) 0.0812(6) Uani 1 1 d . . . O3 O 0.17536(15) 0.9753(2) 0.16529(14) 0.0955(8) Uani 1 1 d . . . O4 O 0.86736(13) 0.6584(2) 0.10124(9) 0.0707(5) Uani 1 1 d . . . O5 O 0.78838(12) 0.50000(17) 0.18758(8) 0.0569(4) Uani 1 1 d . . . O6 O 0.70392(13) 0.70273(16) 0.15011(9) 0.0606(5) Uani 1 1 d . . . S1 S 0.77460(4) 0.60019(6) 0.12691(3) 0.04697(19) Uani 1 1 d . . . H1 H 0.6496(18) 0.667(3) 0.2496(16) 0.064(7) Uiso 1 1 d . . . H2A H 0.705(2) 0.461(3) 0.2908(17) 0.067(9) Uiso 1 1 d . . . H2B H 0.663(2) 0.388(3) 0.3546(17) 0.078(9) Uiso 1 1 d . . . H4A H 0.4529(19) 0.605(3) 0.5165(16) 0.069(8) Uiso 1 1 d . . . H4B H 0.4139(19) 0.743(3) 0.4991(15) 0.065(8) Uiso 1 1 d . . . H6 H 0.5575(14) 0.836(2) 0.2645(12) 0.035(5) Uiso 1 1 d . . . H7A H 0.4534(18) 0.962(3) 0.4090(15) 0.061(8) Uiso 1 1 d . . . H7B H 0.362(2) 0.869(3) 0.4058(16) 0.077(8) Uiso 1 1 d . . . H9 H 0.5155(18) 1.067(2) 0.2827(13) 0.053(7) Uiso 1 1 d . . . H13 H 0.2548(18) 0.882(3) 0.2962(14) 0.061(7) Uiso 1 1 d . . . H18 H 0.6192(19) 0.656(3) 0.0175(15) 0.073(8) Uiso 1 1 d . . . H19 H 0.548(2) 0.545(3) -0.0885(18) 0.102(11) Uiso 1 1 d . . . H21 H 0.744(2) 0.247(3) -0.0540(19) 0.101(11) Uiso 1 1 d . . . H22 H 0.811(2) 0.357(3) 0.0482(18) 0.087(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0486(12) 0.0379(11) 0.0328(10) 0.0033(9) 0.0042(9) 0.0025(9) C4 0.0484(12) 0.0399(11) 0.0327(10) 0.0016(9) 0.0054(9) 0.0033(10) C5 0.0459(11) 0.0371(11) 0.0328(10) 0.0029(9) 0.0023(9) 0.0035(9) C6 0.0553(13) 0.0350(11) 0.0333(10) 0.0077(9) 0.0023(9) 0.0010(10) C7 0.0692(17) 0.0508(14) 0.0424(12) 0.0059(12) 0.0069(12) 0.0183(13) C8 0.0610(15) 0.0408(12) 0.0477(12) 0.0073(10) 0.0054(11) 0.0174(11) C9 0.0585(15) 0.0427(13) 0.0563(14) 0.0058(11) -0.0054(12) 0.0081(12) C10 0.0633(15) 0.0398(12) 0.0571(14) 0.0118(11) 0.0019(11) 0.0026(11) C11 0.0684(16) 0.0481(14) 0.0609(15) 0.0199(12) -0.0125(12) 0.0016(12) C12 0.0575(15) 0.0557(15) 0.0764(17) 0.0193(13) -0.0112(13) 0.0005(12) C13 0.0565(16) 0.0520(15) 0.0692(17) 0.0196(13) 0.0073(13) 0.0077(12) C14 0.071(2) 0.117(3) 0.110(3) 0.045(2) -0.0016(18) -0.0186(19) C15 0.201(5) 0.105(3) 0.071(2) 0.028(2) -0.035(3) -0.019(3) C16 0.071(2) 0.105(3) 0.132(3) 0.048(2) -0.0190(19) -0.0274(19) C17 0.0487(13) 0.0430(12) 0.0399(11) 0.0007(9) 0.0081(10) -0.0058(10) C18 0.0787(19) 0.0572(17) 0.0644(16) -0.0137(13) -0.0104(14) 0.0138(14) C19 0.084(2) 0.082(2) 0.0738(19) -0.0093(17) -0.0261(17) 0.0125(18) C20 0.0824(19) 0.0657(17) 0.0588(15) -0.0141(14) -0.0057(14) -0.0090(15) C21 0.098(2) 0.0550(17) 0.0741(19) -0.0182(15) -0.0071(17) 0.0126(16) C22 0.0766(18) 0.0559(16) 0.0610(16) -0.0073(13) -0.0094(14) 0.0130(14) C23 0.132(3) 0.108(3) 0.087(2) -0.036(2) -0.029(2) -0.011(2) N1 0.0505(11) 0.0405(10) 0.0335(9) 0.0050(8) 0.0110(8) 0.0056(8) N2 0.0800(16) 0.0470(12) 0.0492(12) 0.0109(10) 0.0256(11) 0.0207(11) N3 0.0579(11) 0.0400(10) 0.0330(9) 0.0065(7) 0.0102(8) 0.0091(8) N4 0.0788(15) 0.0498(12) 0.0404(10) 0.0118(9) 0.0230(10) 0.0212(11) O1 0.0734(12) 0.0667(12) 0.0788(12) 0.0339(10) -0.0055(10) -0.0121(10) O2 0.0935(14) 0.0721(13) 0.0774(14) 0.0367(11) -0.0281(11) -0.0093(11) O3 0.0718(13) 0.0951(16) 0.1188(18) 0.0564(14) -0.0320(12) -0.0209(12) O4 0.0701(11) 0.0944(14) 0.0479(9) 0.0049(9) 0.0091(8) -0.0386(10) O5 0.0673(11) 0.0625(10) 0.0412(8) 0.0102(7) 0.0075(7) -0.0032(8) O6 0.0892(12) 0.0482(9) 0.0446(9) -0.0037(7) 0.0129(8) 0.0029(9) S1 0.0571(4) 0.0492(3) 0.0348(3) 0.0020(2) 0.0094(2) -0.0124(3) _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 C2 N2 1.323(3) . ? C2 N3 1.330(3) . ? C2 N1 1.346(3) . ? C4 N4 1.323(3) . ? C4 N3 1.347(3) . ? C4 C5 1.438(3) . ? C5 C6 1.343(3) . ? C5 C7 1.519(3) . ? C6 N1 1.354(3) . ? C7 C8 1.519(3) . ? C8 C13 1.373(4) . ? C8 C9 1.388(3) . ? C9 C10 1.394(3) . ? C10 O1 1.369(3) . ? C10 C11 1.378(3) . ? C11 O2 1.381(3) . ? C11 C12 1.390(3) . ? C12 O3 1.373(3) . ? C12 C13 1.388(4) . ? C14 O1 1.403(3) . ? C15 O2 1.399(4) . ? C16 O3 1.420(3) . ? C17 C18 1.366(3) . ? C17 C22 1.374(3) . ? C17 S1 1.763(2) . ? C18 C19 1.387(4) . ? C19 C20 1.370(4) . ? C20 C21 1.362(4) . ? C20 C23 1.516(4) . ? C21 C22 1.382(4) . ? O4 S1 1.4465(16) . ? O5 S1 1.4561(16) . ? O6 S1 1.4571(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 N2 C2 N3 120.51(19) . . ? N2 C2 N1 118.27(19) . . ? N3 C2 N1 121.23(18) . . ? N4 C4 N3 116.12(19) . . ? N4 C4 C5 121.3(2) . . ? N3 C4 C5 122.58(17) . . ? C6 C5 C4 114.51(19) . . ? C6 C5 C7 123.25(19) . . ? C4 C5 C7 122.23(18) . . ? C5 C6 N1 122.4(2) . . ? C8 C7 C5 113.42(18) . . ? C13 C8 C9 120.1(2) . . ? C13 C8 C7 119.4(2) . . ? C9 C8 C7 120.4(2) . . ? C8 C9 C10 119.7(2) . . ? O1 C10 C11 115.8(2) . . ? O1 C10 C9 124.1(2) . . ? C11 C10 C9 120.1(2) . . ? C10 C11 O2 119.9(2) . . ? C10 C11 C12 119.8(2) . . ? O2 C11 C12 120.3(2) . . ? O3 C12 C13 124.8(2) . . ? O3 C12 C11 115.2(2) . . ? C13 C12 C11 119.9(2) . . ? C8 C13 C12 120.2(2) . . ? C18 C17 C22 119.8(2) . . ? C18 C17 S1 120.50(19) . . ? C22 C17 S1 119.72(19) . . ? C17 C18 C19 119.7(3) . . ? C20 C19 C18 121.1(3) . . ? C21 C20 C19 118.3(3) . . ? C21 C20 C23 121.7(3) . . ? C19 C20 C23 120.0(3) . . ? C20 C21 C22 121.5(3) . . ? C17 C22 C21 119.5(3) . . ? C2 N1 C6 120.48(18) . . ? C2 N3 C4 118.53(17) . . ? C10 O1 C14 118.5(2) . . ? C11 O2 C15 114.3(2) . . ? C12 O3 C16 117.2(2) . . ? O4 S1 O5 113.11(11) . . ? O4 S1 O6 111.17(11) . . ? O5 S1 O6 111.82(10) . . ? O4 S1 C17 106.79(10) . . ? O5 S1 C17 106.65(10) . . ? O6 S1 C17 106.86(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.200 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.041 #============================================================================= data_for_compound_2 _database_code_CSD 192070 _chemical_name_systematic ; [2,4-diamino-5-(3',4',5'-trimethoxybenzyl pyrimidinium)] 4-aminobenzene sulfonate ; _chemical_name_common 'Trimethoprim sulfanilate monohydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H27 N5 O7 S' _chemical_formula_weight 481.53 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.855(4) _cell_length_b 6.136(10) _cell_length_c 21.349(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.080(3) _cell_angle_gamma 90.00 _cell_volume 2210(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6751 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.200 _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 'Kuma KM4CCD \k-geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 16161 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.06 _reflns_number_total 3918 _reflns_number_gt 3380 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; KUMA KM4CCD software(Kuma diffraction, 1999) ; _computing_cell_refinement 'KUMA KM4CCD software' _computing_data_reduction 'KUMA KM4CCD software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON97 (Spek, 1997)' _computing_publication_material 'PLATON97 (Spek, 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^)+(0.1000P)^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 3918 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1630 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.88411(5) 0.88413(13) 0.16318(4) 0.0154(2) Uani 1 1 d . . . O4 O 0.93717(13) 0.9905(4) 0.22167(11) 0.0217(6) Uani 1 1 d . . . O5 O 0.88191(13) 0.6482(4) 0.17059(11) 0.0207(6) Uani 1 1 d . . . O2 O 0.52125(13) 0.1503(4) 0.40033(11) 0.0192(5) Uani 1 1 d . . . O3 O 0.55863(13) 0.4478(4) 0.32300(11) 0.0201(6) Uani 1 1 d . . . O6 O 0.89885(13) 0.9456(4) 0.10225(11) 0.0193(5) Uani 1 1 d . . . O1 O 0.62543(13) -0.1608(4) 0.46285(12) 0.0215(6) Uani 1 1 d . . . O7 O 0.91837(15) 0.6061(4) 0.02253(13) 0.0237(6) Uani 1 1 d . . . N3 N 0.93432(15) 0.6020(4) 0.41937(13) 0.0157(6) Uani 1 1 d . . . N5 N 0.56424(18) 1.2184(6) 0.14245(17) 0.0286(8) Uani 1 1 d . . . N4 N 0.88371(17) 0.3463(5) 0.47284(15) 0.0187(7) Uani 1 1 d . . . N1 N 0.91593(16) 0.5655(4) 0.30636(15) 0.0167(6) Uani 1 1 d . . . N2 N 0.98619(17) 0.8542(5) 0.36463(17) 0.0186(7) Uani 1 1 d . . . C5 C 0.86149(18) 0.2937(5) 0.35672(16) 0.0147(7) Uani 1 1 d . . . C12 C 0.61357(18) 0.2893(5) 0.34937(16) 0.0161(7) Uani 1 1 d . . . C11 C 0.59435(18) 0.1401(5) 0.39115(17) 0.0174(7) Uani 1 1 d . . . C10 C 0.64820(19) -0.0233(6) 0.42165(16) 0.0182(7) Uani 1 1 d . . . C2 C 0.94587(18) 0.6726(5) 0.36373(16) 0.0154(7) Uani 1 1 d . . . C21 C 0.6913(2) 1.2688(6) 0.12635(17) 0.0193(7) Uani 1 1 d . . . C20 C 0.6374(2) 1.1409(6) 0.14581(17) 0.0195(8) Uani 1 1 d . . . C16 C 0.5757(2) 0.6018(6) 0.27860(19) 0.0232(8) Uani 1 1 d . . . C4 C 0.89430(18) 0.4158(5) 0.41712(16) 0.0147(7) Uani 1 1 d . . . C6 C 0.87462(19) 0.3767(5) 0.30266(17) 0.0165(7) Uani 1 1 d . . . C9 C 0.72052(19) -0.0387(6) 0.40988(17) 0.0175(7) Uani 1 1 d . . . C19 C 0.6615(2) 0.9307(6) 0.17015(17) 0.0212(8) Uani 1 1 d . . . C14 C 0.6830(2) -0.3150(6) 0.4991(2) 0.0248(8) Uani 1 1 d . . . C8 C 0.73835(18) 0.1078(5) 0.36760(16) 0.0163(7) Uani 1 1 d . . . C17 C 0.78811(18) 0.9807(5) 0.15511(16) 0.0158(7) Uani 1 1 d . . . C13 C 0.68526(19) 0.2714(6) 0.33699(17) 0.0175(7) Uani 1 1 d . . . C15 C 0.5235(2) 0.2581(7) 0.4608(2) 0.0262(9) Uani 1 1 d . . . C7 C 0.81670(19) 0.0838(5) 0.35421(17) 0.0162(7) Uani 1 1 d . . . C18 C 0.73588(19) 0.8522(6) 0.17496(16) 0.0170(7) Uani 1 1 d . . . C22 C 0.76554(19) 1.1909(5) 0.13109(17) 0.0179(7) Uani 1 1 d . . . H22 H 0.8007(18) 1.286(5) 0.1162(15) 0.005(7) Uiso 1 1 d . . . H13 H 0.700(2) 0.370(6) 0.3099(18) 0.021(9) Uiso 1 1 d . . . H16B H 0.626(2) 0.689(5) 0.3021(16) 0.012(8) Uiso 1 1 d . . . H7A H 0.8054(19) 0.013(6) 0.3097(18) 0.019(9) Uiso 1 1 d . . . H2A H 0.9949(19) 0.903(5) 0.3290(18) 0.011(9) Uiso 1 1 d . . . H6 H 0.856(2) 0.314(6) 0.2590(18) 0.019(9) Uiso 1 1 d . . . H9 H 0.759(2) -0.142(5) 0.4339(17) 0.016(9) Uiso 1 1 d . . . H1 H 0.929(2) 0.603(5) 0.2735(18) 0.016(9) Uiso 1 1 d . . . H19 H 0.624(2) 0.847(6) 0.1842(18) 0.029(10) Uiso 1 1 d . . . H15C H 0.567(3) 0.206(7) 0.499(2) 0.043(12) Uiso 1 1 d . . . H7B H 0.850(2) -0.021(6) 0.3845(18) 0.021(9) Uiso 1 1 d . . . H21 H 0.670(2) 1.410(6) 0.1079(17) 0.018(9) Uiso 1 1 d . . . H18 H 0.7491(19) 0.700(6) 0.1903(17) 0.017(9) Uiso 1 1 d . . . H14C H 0.660(3) -0.386(7) 0.533(2) 0.047(12) Uiso 1 1 d . . . H4A H 0.906(2) 0.422(6) 0.510(2) 0.025(10) Uiso 1 1 d . . . H14B H 0.733(3) -0.242(7) 0.528(2) 0.043(12) Uiso 1 1 d . . . H15A H 0.532(3) 0.419(8) 0.456(2) 0.053(14) Uiso 1 1 d . . . H15B H 0.474(2) 0.239(6) 0.4656(18) 0.026(10) Uiso 1 1 d . . . H2B H 1.012(2) 0.923(6) 0.402(2) 0.024(11) Uiso 1 1 d . . . H7D H 0.913(3) 0.699(8) 0.055(2) 0.053(14) Uiso 1 1 d . . . H4B H 0.858(3) 0.202(7) 0.475(2) 0.044(12) Uiso 1 1 d . . . H16A H 0.528(3) 0.696(7) 0.265(2) 0.047(13) Uiso 1 1 d . . . H5A H 0.547(2) 1.344(7) 0.124(2) 0.036(12) Uiso 1 1 d . . . H5B H 0.529(3) 1.123(7) 0.149(2) 0.043(13) Uiso 1 1 d . . . H16C H 0.579(2) 0.529(6) 0.238(2) 0.034(11) Uiso 1 1 d . . . H14A H 0.699(2) -0.424(6) 0.4679(19) 0.026(10) Uiso 1 1 d . . . H7C H 0.932(3) 0.691(8) -0.006(3) 0.060(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0161(4) 0.0178(5) 0.0128(4) -0.0002(3) 0.0056(3) -0.0005(3) O4 0.0169(12) 0.0307(14) 0.0163(13) -0.0048(11) 0.0038(10) -0.0021(10) O5 0.0254(13) 0.0175(13) 0.0205(13) 0.0037(10) 0.0094(11) 0.0037(10) O2 0.0135(11) 0.0273(14) 0.0181(13) -0.0032(10) 0.0068(10) -0.0010(10) O3 0.0171(12) 0.0213(13) 0.0223(13) 0.0059(10) 0.0072(10) 0.0045(10) O6 0.0231(12) 0.0210(13) 0.0169(13) 0.0020(10) 0.0108(10) -0.0005(10) O1 0.0206(12) 0.0215(13) 0.0246(14) 0.0089(10) 0.0104(11) 0.0008(10) O7 0.0376(15) 0.0154(13) 0.0212(14) -0.0001(12) 0.0138(12) 0.0025(11) N3 0.0175(14) 0.0131(14) 0.0167(15) 0.0011(12) 0.0057(12) 0.0002(11) N5 0.0211(17) 0.0264(19) 0.041(2) 0.0047(16) 0.0139(15) 0.0051(15) N4 0.0252(16) 0.0164(16) 0.0137(16) -0.0014(13) 0.0052(13) -0.0068(13) N1 0.0190(15) 0.0174(15) 0.0170(16) 0.0032(12) 0.0107(13) 0.0010(11) N2 0.0201(15) 0.0180(16) 0.0197(18) 0.0049(14) 0.0090(14) -0.0023(12) C5 0.0122(15) 0.0154(17) 0.0159(18) -0.0010(14) 0.0039(13) 0.0040(13) C12 0.0130(16) 0.0174(17) 0.0145(17) -0.0049(14) -0.0003(13) -0.0003(13) C11 0.0107(15) 0.0221(18) 0.0194(18) -0.0045(15) 0.0047(14) -0.0019(13) C10 0.0194(17) 0.0198(18) 0.0157(18) -0.0017(14) 0.0059(14) -0.0056(14) C2 0.0129(15) 0.0187(18) 0.0153(18) 0.0010(14) 0.0056(13) 0.0061(13) C21 0.0219(18) 0.0148(18) 0.0197(19) -0.0014(15) 0.0046(15) -0.0004(14) C20 0.0194(17) 0.0216(19) 0.0171(18) -0.0048(14) 0.0055(14) -0.0020(14) C16 0.027(2) 0.021(2) 0.022(2) 0.0072(16) 0.0080(17) 0.0024(16) C4 0.0149(16) 0.0147(17) 0.0158(17) 0.0009(14) 0.0066(13) 0.0045(13) C6 0.0138(16) 0.0201(18) 0.0159(19) -0.0018(15) 0.0053(14) 0.0013(14) C9 0.0144(16) 0.0175(18) 0.0186(18) 0.0019(15) 0.0026(14) 0.0003(14) C19 0.0195(18) 0.025(2) 0.0216(19) 0.0018(15) 0.0095(15) -0.0037(15) C14 0.026(2) 0.026(2) 0.022(2) 0.0091(17) 0.0072(17) 0.0034(16) C8 0.0165(16) 0.0174(17) 0.0146(18) -0.0060(14) 0.0044(14) -0.0030(13) C17 0.0165(16) 0.0179(17) 0.0117(17) -0.0041(14) 0.0030(13) -0.0013(13) C13 0.0187(17) 0.0187(18) 0.0165(18) 0.0011(15) 0.0074(14) -0.0002(14) C15 0.022(2) 0.035(2) 0.025(2) -0.0035(18) 0.0124(17) 0.0012(17) C7 0.0176(17) 0.0162(18) 0.0149(18) -0.0032(15) 0.0055(14) -0.0022(14) C18 0.0195(17) 0.0150(18) 0.0163(18) 0.0011(14) 0.0053(14) -0.0017(14) C22 0.0186(17) 0.0182(18) 0.0160(18) -0.0001(14) 0.0046(14) -0.0036(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 S1 O4 1.452(2) . ? S1 O5 1.458(3) . ? S1 O6 1.458(2) . ? S1 C17 1.768(3) . ? O2 C11 1.383(4) . ? O2 C15 1.440(4) . ? O3 C12 1.366(4) . ? O3 C16 1.440(4) . ? O1 C10 1.373(4) . ? O1 C14 1.425(4) . ? N3 C4 1.340(4) . ? N3 C2 1.342(4) . ? N5 C20 1.370(4) . ? N4 C4 1.334(4) . ? N1 C2 1.338(4) . ? N1 C6 1.362(5) . ? N2 C2 1.323(5) . ? C5 C6 1.350(5) . ? C5 C4 1.440(5) . ? C5 C7 1.508(5) . ? C12 C13 1.394(4) . ? C12 C11 1.397(5) . ? C11 C10 1.394(5) . ? C10 C9 1.397(5) . ? C21 C22 1.381(5) . ? C21 C20 1.406(5) . ? C20 C19 1.405(5) . ? C9 C8 1.383(5) . ? C19 C18 1.385(5) . ? C8 C13 1.389(5) . ? C8 C7 1.524(4) . ? C17 C18 1.389(5) . ? C17 C22 1.397(5) . ? 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 O4 S1 O5 112.70(15) . . ? O4 S1 O6 113.18(14) . . ? O5 S1 O6 111.87(14) . . ? O4 S1 C17 105.80(15) . . ? O5 S1 C17 106.48(15) . . ? O6 S1 C17 106.16(15) . . ? C11 O2 C15 113.4(3) . . ? C12 O3 C16 117.4(3) . . ? C10 O1 C14 116.3(3) . . ? C4 N3 C2 118.6(3) . . ? C2 N1 C6 121.2(3) . . ? C6 C5 C4 115.8(3) . . ? C6 C5 C7 122.0(3) . . ? C4 C5 C7 122.1(3) . . ? O3 C12 C13 123.9(3) . . ? O3 C12 C11 115.9(3) . . ? C13 C12 C11 120.2(3) . . ? O2 C11 C10 120.3(3) . . ? O2 C11 C12 120.1(3) . . ? C10 C11 C12 119.6(3) . . ? O1 C10 C11 116.0(3) . . ? O1 C10 C9 123.9(3) . . ? C11 C10 C9 120.1(3) . . ? N2 C2 N1 118.7(3) . . ? N2 C2 N3 120.0(3) . . ? N1 C2 N3 121.4(3) . . ? C22 C21 C20 121.2(3) . . ? N5 C20 C19 120.6(3) . . ? N5 C20 C21 121.6(3) . . ? C19 C20 C21 117.8(3) . . ? N4 C4 N3 118.0(3) . . ? N4 C4 C5 119.8(3) . . ? N3 C4 C5 122.1(3) . . ? C5 C6 N1 120.9(3) . . ? C8 C9 C10 119.8(3) . . ? C18 C19 C20 121.1(3) . . ? C9 C8 C13 120.7(3) . . ? C9 C8 C7 118.8(3) . . ? C13 C8 C7 120.6(3) . . ? C18 C17 C22 119.6(3) . . ? C18 C17 S1 120.4(3) . . ? C22 C17 S1 119.9(2) . . ? C8 C13 C12 119.7(3) . . ? C5 C7 C8 114.8(3) . . ? C19 C18 C17 120.2(3) . . ? C21 C22 C17 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.183 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.055 data_for_compound_1 _database_code_CSD 200798 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium] benzenesulfonate, monohydrate. ; _chemical_name_common ; (2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium) benzenesulfonate, monohydrate. ; _chemical_melting_point ? _chemical_formula_moiety (C14H19N4O3+),(C6H5SO3-).H20 _chemical_formula_sum 'C20 H26 N4 O7 S' _chemical_formula_weight 466.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.507(2) _cell_length_b 6.323(3) _cell_length_c 21.350(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.80(2) _cell_angle_gamma 90.00 _cell_volume 2250.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Plate shaped crystal' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.193 _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 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart diffractometer' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17125 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.1294 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4924 _reflns_number_gt 2022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS Smart Single Crystal with CCD' _computing_cell_refinement 'Bruker AXS Smart Single Crystal with CCD' _computing_data_reduction 'Bruker AXS Smart Single Crystal with CCD' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1997)' _computing_publication_material 'PLATON (Spek, 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^)+(0.0382P)^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 4924 _refine_ls_number_parameters 393 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1560 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 0.714 _refine_ls_restrained_S_all 0.714 _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 S S 0.62089(4) 0.11062(11) 0.33943(3) 0.0472(2) Uani 1 1 d . . . N3 N 0.56671(11) 0.3887(3) 0.08150(9) 0.0391(5) Uani 1 1 d . . . O5 O 0.60077(10) 0.0561(3) 0.39828(8) 0.0565(5) Uani 1 1 d . . . O2 O 0.98582(10) 0.8850(3) 0.10033(10) 0.0625(5) Uani 1 1 d . . . N4 N 0.61688(15) 0.6429(4) 0.02933(12) 0.0507(7) Uani 1 1 d . . . N1 N 0.58715(13) 0.4145(4) 0.19483(12) 0.0467(6) Uani 1 1 d . . . C5 C 0.64064(14) 0.6865(4) 0.14507(12) 0.0380(6) Uani 1 1 d . . . O1W O 0.41702(14) 0.9015(4) 0.02286(12) 0.0664(6) Uani 1 1 d . . . C4 C 0.60749(13) 0.5715(4) 0.08495(12) 0.0367(6) Uani 1 1 d . . . O1 O 0.95265(10) 0.5796(3) 0.17405(9) 0.0612(5) Uani 1 1 d . . . O4 O 0.56722(10) 0.0179(3) 0.27973(8) 0.0606(5) Uani 1 1 d . . . C2 C 0.55547(15) 0.3162(4) 0.13697(14) 0.0401(6) Uani 1 1 d . . . N2 N 0.51327(15) 0.1407(4) 0.13538(15) 0.0521(7) Uani 1 1 d . . . C6 C 0.62855(16) 0.5994(5) 0.19876(14) 0.0474(7) Uani 1 1 d . . . O6 O 0.63000(12) 0.3379(3) 0.33314(9) 0.0639(6) Uani 1 1 d . . . C7 C 0.68428(17) 0.8931(5) 0.14803(16) 0.0468(7) Uani 1 1 d . . . C8 C 0.76406(14) 0.8818(4) 0.13406(12) 0.0407(6) Uani 1 1 d . . . C11 C 0.91085(15) 0.8804(4) 0.10942(13) 0.0462(7) Uani 1 1 d . . . C12 C 0.85442(16) 1.0327(4) 0.08104(13) 0.0475(7) Uani 1 1 d . . . C13 C 0.78068(16) 1.0326(4) 0.09302(14) 0.0456(7) Uani 1 1 d . . . C10 C 0.89373(15) 0.7256(4) 0.14927(13) 0.0453(7) Uani 1 1 d . . . C18 C 0.77213(19) 0.0997(6) 0.32611(15) 0.0615(8) Uani 1 1 d . . . O3 O 0.87589(11) 1.1777(3) 0.04177(10) 0.0662(6) Uani 1 1 d . . . C17 C 0.71596(15) -0.0050(4) 0.34812(13) 0.0455(7) Uani 1 1 d . . . C9 C 0.81999(16) 0.7275(5) 0.16191(13) 0.0461(7) Uani 1 1 d . . . C22 C 0.7323(2) -0.2056(5) 0.37479(16) 0.0650(9) Uani 1 1 d . . . C20 C 0.8616(3) -0.1937(9) 0.3584(2) 0.0972(15) Uani 1 1 d . . . C16 C 0.8178(3) 1.3305(7) 0.0091(2) 0.0750(11) Uani 1 1 d . . . C15 C 0.9908(3) 0.7548(8) 0.0471(2) 0.0843(12) Uani 1 1 d . . . C14 C 0.9378(3) 0.4144(7) 0.2143(2) 0.0753(11) Uani 1 1 d . . . C19 C 0.8447(2) 0.0033(9) 0.3315(2) 0.0866(13) Uani 1 1 d . . . C21 C 0.8053(3) -0.2992(7) 0.3795(2) 0.0881(12) Uani 1 1 d . . . H9 H 0.8100(13) 0.621(3) 0.1875(11) 0.043(7) Uiso 1 1 d . . . H7B H 0.6914(12) 0.945(3) 0.1910(11) 0.038(7) Uiso 1 1 d . . . H13 H 0.7430(12) 1.137(3) 0.0761(10) 0.029(6) Uiso 1 1 d . . . H7A H 0.6502(14) 0.987(4) 0.1161(12) 0.055(8) Uiso 1 1 d . . . H2A H 0.5090(18) 0.099(5) 0.1740(15) 0.097(12) Uiso 1 1 d . . . H16B H 0.7682(19) 1.251(5) -0.0197(15) 0.102(13) Uiso 1 1 d . . . H4A H 0.5972(17) 0.570(5) -0.0089(14) 0.083(11) Uiso 1 1 d . . . H14C H 0.9839(17) 0.331(4) 0.2234(13) 0.079(11) Uiso 1 1 d . . . H4B H 0.6377(14) 0.765(4) 0.0280(11) 0.044(8) Uiso 1 1 d . . . H16A H 0.8428(17) 1.409(4) -0.0179(15) 0.091(11) Uiso 1 1 d . . . H18 H 0.7587(14) 0.246(4) 0.3093(12) 0.060(9) Uiso 1 1 d . . . H2W H 0.4054(19) 0.805(5) 0.0532(18) 0.121(14) Uiso 1 1 d . . . H14B H 0.927(2) 0.477(5) 0.2526(17) 0.114(15) Uiso 1 1 d . . . H1 H 0.5828(15) 0.370(4) 0.2330(13) 0.073(10) Uiso 1 1 d . . . H2B H 0.4890(15) 0.070(4) 0.0970(13) 0.061(10) Uiso 1 1 d . . . H14A H 0.889(2) 0.333(5) 0.1919(17) 0.118(14) Uiso 1 1 d . . . H16C H 0.8037(16) 1.412(4) 0.0402(14) 0.074(11) Uiso 1 1 d . . . H22 H 0.6942(17) -0.272(5) 0.3910(14) 0.082(11) Uiso 1 1 d . . . H15A H 1.042(2) 0.790(5) 0.0445(15) 0.099(12) Uiso 1 1 d . . . H21 H 0.8157(19) -0.445(5) 0.3986(16) 0.107(13) Uiso 1 1 d . . . H15C H 0.984(2) 0.587(6) 0.0588(18) 0.129(15) Uiso 1 1 d . . . H15B H 0.948(2) 0.794(5) 0.0069(18) 0.115(15) Uiso 1 1 d . . . H20 H 0.914(2) -0.261(5) 0.3638(16) 0.115(13) Uiso 1 1 d . . . H19 H 0.878(2) 0.081(5) 0.3182(18) 0.116(16) Uiso 1 1 d . . . H1W H 0.4310(19) 0.837(5) -0.0051(16) 0.097(15) Uiso 1 1 d . . . H6 H 0.6497(14) 0.661(4) 0.2427(12) 0.060(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0515(4) 0.0541(5) 0.0384(4) -0.0003(4) 0.0174(4) -0.0056(4) N3 0.0393(12) 0.0426(13) 0.0354(13) 0.0019(11) 0.0113(10) -0.0017(11) O5 0.0725(14) 0.0679(13) 0.0377(11) 0.0025(10) 0.0295(10) -0.0065(10) O2 0.0367(12) 0.0769(14) 0.0756(15) -0.0017(12) 0.0196(10) -0.0024(10) N4 0.0706(18) 0.0460(17) 0.0358(16) -0.0036(13) 0.0167(14) -0.0179(14) N1 0.0512(15) 0.0582(17) 0.0355(15) 0.0045(13) 0.0204(12) 0.0016(13) C5 0.0348(15) 0.0449(17) 0.0373(16) -0.0027(13) 0.0152(13) 0.0006(12) O1W 0.0928(17) 0.0541(14) 0.0579(15) 0.0035(13) 0.0315(13) -0.0069(13) C4 0.0343(15) 0.0442(17) 0.0315(16) 0.0033(13) 0.0096(12) 0.0038(13) O1 0.0483(12) 0.0613(13) 0.0691(14) 0.0117(12) 0.0107(10) 0.0117(10) O4 0.0501(12) 0.0896(14) 0.0391(11) -0.0118(10) 0.0093(10) -0.0126(11) C2 0.0367(16) 0.0407(17) 0.0447(18) 0.0064(14) 0.0150(14) 0.0106(13) N2 0.0551(16) 0.0479(17) 0.057(2) 0.0034(15) 0.0231(15) -0.0035(13) C6 0.0444(17) 0.060(2) 0.0390(18) -0.0084(17) 0.0146(14) -0.0002(16) O6 0.0861(15) 0.0438(12) 0.0681(14) 0.0060(10) 0.0328(12) 0.0001(11) C7 0.0486(18) 0.0469(18) 0.0466(19) -0.0097(17) 0.0170(16) -0.0020(16) C8 0.0371(15) 0.0454(16) 0.0383(16) -0.0063(14) 0.0097(13) -0.0028(14) C11 0.0334(16) 0.0572(18) 0.0468(17) -0.0014(15) 0.0105(13) -0.0020(15) C12 0.0395(17) 0.0530(18) 0.0489(19) 0.0013(14) 0.0121(14) -0.0050(15) C13 0.0382(17) 0.0449(18) 0.0497(19) 0.0026(14) 0.0074(15) 0.0043(15) C10 0.0365(17) 0.0470(17) 0.0468(18) -0.0033(14) 0.0044(14) 0.0037(14) C18 0.057(2) 0.073(2) 0.057(2) -0.0056(19) 0.0205(17) -0.005(2) O3 0.0561(13) 0.0697(14) 0.0771(15) 0.0260(12) 0.0266(11) 0.0035(11) C17 0.0460(17) 0.0470(17) 0.0400(17) -0.0067(13) 0.0082(14) -0.0069(14) C9 0.0488(19) 0.0482(19) 0.0409(18) -0.0001(15) 0.0129(15) -0.0069(16) C22 0.064(2) 0.060(2) 0.064(2) -0.0094(18) 0.0076(19) -0.005(2) C20 0.067(3) 0.131(4) 0.084(3) -0.028(3) 0.009(2) 0.028(3) C16 0.075(3) 0.075(3) 0.077(3) 0.026(2) 0.028(3) 0.010(2) C15 0.060(3) 0.126(4) 0.076(3) -0.003(3) 0.034(2) 0.013(3) C14 0.069(3) 0.061(3) 0.086(3) 0.017(2) 0.010(2) 0.016(2) C19 0.059(3) 0.129(4) 0.075(3) -0.010(3) 0.026(2) -0.008(3) C21 0.091(3) 0.070(3) 0.087(3) -0.015(2) 0.003(3) 0.017(3) _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 S O5 1.4465(16) . ? S O4 1.4557(17) . ? S O6 1.4564(18) . ? S C17 1.775(3) . ? N3 C2 1.339(3) . ? N3 C4 1.348(3) . ? O2 C11 1.385(3) . ? O2 C15 1.427(4) . ? N4 C4 1.327(3) . ? N1 C2 1.342(3) . ? N1 C6 1.365(3) . ? C5 C6 1.345(3) . ? C5 C4 1.435(3) . ? C5 C7 1.505(3) . ? O1 C10 1.365(3) . ? O1 C14 1.426(4) . ? C2 N2 1.327(3) . ? C7 C8 1.517(3) . ? C8 C9 1.381(3) . ? C8 C13 1.384(3) . ? C11 C12 1.380(3) . ? C11 C10 1.388(3) . ? C12 O3 1.370(3) . ? C12 C13 1.391(3) . ? C10 C9 1.397(3) . ? C18 C17 1.382(4) . ? C18 C19 1.382(5) . ? O3 C16 1.421(4) . ? C17 C22 1.384(4) . ? C22 C21 1.384(5) . ? C20 C19 1.366(6) . ? C20 C21 1.375(5) . ? 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 O5 S O4 113.66(11) . . ? O5 S O6 112.18(11) . . ? O4 S O6 112.11(12) . . ? O5 S C17 106.30(12) . . ? O4 S C17 105.02(12) . . ? O6 S C17 106.88(13) . . ? C2 N3 C4 117.6(2) . . ? C11 O2 C15 113.0(2) . . ? C2 N1 C6 121.1(2) . . ? C6 C5 C4 115.4(2) . . ? C6 C5 C7 122.0(3) . . ? C4 C5 C7 122.6(2) . . ? N4 C4 N3 116.8(2) . . ? N4 C4 C5 120.1(2) . . ? N3 C4 C5 123.1(2) . . ? C10 O1 C14 118.3(2) . . ? N2 C2 N3 119.6(3) . . ? N2 C2 N1 118.7(3) . . ? N3 C2 N1 121.6(3) . . ? C5 C6 N1 121.1(3) . . ? C5 C7 C8 115.9(2) . . ? C9 C8 C13 120.0(2) . . ? C9 C8 C7 121.5(3) . . ? C13 C8 C7 118.4(3) . . ? C12 C11 O2 120.4(2) . . ? C12 C11 C10 120.1(2) . . ? O2 C11 C10 119.5(2) . . ? O3 C12 C11 116.2(2) . . ? O3 C12 C13 123.8(3) . . ? C11 C12 C13 119.9(3) . . ? C8 C13 C12 120.2(3) . . ? O1 C10 C11 115.8(2) . . ? O1 C10 C9 124.4(3) . . ? C11 C10 C9 119.8(3) . . ? C17 C18 C19 119.5(4) . . ? C12 O3 C16 117.8(2) . . ? C18 C17 C22 120.0(3) . . ? C18 C17 S 120.6(2) . . ? C22 C17 S 119.3(2) . . ? C8 C9 C10 119.9(3) . . ? C21 C22 C17 119.5(4) . . ? C19 C20 C21 119.7(4) . . ? C20 C19 C18 120.8(4) . . ? C20 C21 C22 120.5(4) . . ? _diffrn_measured_fraction_theta_max 0.876 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.876 _refine_diff_density_max 0.141 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.033 #============================================================================= data_compound_4 _database_code_CSD 200799 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium 3-carboxy-4-hydroxybenzene sulfonate dihydrate ; _chemical_name_common ; 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium 3- carboxy-4-hydroxybenzene sulfonate dihydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C14H19N4O3,C7H5O6S, 2H2O' _chemical_formula_sum 'C21 H28 N4 O11 S' _chemical_formula_weight 544.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.442(2) _cell_length_b 18.769(3) _cell_length_c 12.783(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.18(3) _cell_angle_gamma 90.00 _cell_volume 2504.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.4 _exptl_crystal_description 'plate like' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS smart with CCD' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% negligible _diffrn_reflns_number 21406 _diffrn_reflns_av_R_equivalents 0.1402 _diffrn_reflns_av_sigmaI/netI 0.2647 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.43 _reflns_number_total 5595 _reflns_number_gt 1718 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MolEN (Fair, 1990)' _computing_cell_refinement 'MolEN (Fair, 1990)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1997)' _computing_publication_material 'PLATON (Spek, 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^)+(0.0106P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5595 _refine_ls_number_parameters 435 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.2598 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 0.793 _refine_ls_restrained_S_all 0.796 _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 O6 O -0.0958(3) 0.19659(15) 0.3823(2) 0.0662(10) Uani 1 1 d . . . O8 O -0.0679(3) 0.20271(17) 0.0274(2) 0.0575(9) Uani 1 1 d . . . S S -0.05961(12) 0.12314(7) 0.41811(9) 0.0487(3) Uani 1 1 d . . . O5 O 0.0462(3) 0.11843(14) 0.53221(19) 0.0605(8) Uani 1 1 d . . . C23 C 0.0026(4) 0.1467(2) 0.0376(3) 0.0442(11) Uani 1 1 d . . . C22 C -0.0224(4) 0.1275(2) 0.2208(3) 0.0412(11) Uani 1 1 d . . . O9 O 0.0492(3) 0.13036(14) -0.0299(2) 0.0591(9) Uani 1 1 d . . . O1W O 0.3811(4) 0.5444(2) 0.0234(3) 0.1187(14) Uani 1 1 d D . . O4 O -0.1660(3) 0.07848(16) 0.4105(2) 0.0665(9) Uani 1 1 d . . . C17 C 0.0247(4) 0.1035(2) 0.1417(3) 0.0378(11) Uani 1 1 d . . . C21 C 0.0009(4) 0.0898(2) 0.3192(3) 0.0368(10) Uani 1 1 d . . . C18 C 0.0950(4) 0.0411(2) 0.1640(3) 0.0468(11) Uani 1 1 d . . . C20 C 0.0685(4) 0.0271(2) 0.3414(3) 0.0470(12) Uani 1 1 d . . . C16 C 0.2820(6) 0.4967(3) 0.3534(5) 0.0680(17) Uani 1 1 d . . . O7 O 0.1477(3) 0.01546(16) 0.0931(3) 0.0652(10) Uani 1 1 d D . . C19 C 0.1164(5) 0.0029(2) 0.2640(4) 0.0532(14) Uani 1 1 d . . . O1 O 0.3651(3) 0.44365(16) 0.3426(2) 0.0592(9) Uani 1 1 d . . . O2W O 0.3237(4) 0.4165(2) 0.1051(3) 0.0739(10) Uani 1 1 d D . . C15 C 0.6296(4) 0.3829(3) 0.3173(3) 0.0871(17) Uani 1 1 d . . . H15A H 0.6394 0.4279 0.3558 0.131 Uiso 1 1 calc R . . H15B H 0.6196 0.3908 0.2399 0.131 Uiso 1 1 calc R . . H15C H 0.7042 0.3542 0.3568 0.131 Uiso 1 1 calc R . . C12 C 0.4270(4) 0.4000(2) 0.4352(3) 0.0420(11) Uani 1 1 d . . . C13 C 0.4132(4) 0.4046(2) 0.5378(3) 0.0452(12) Uani 1 1 d . . . O2 O 0.5199(3) 0.34743(14) 0.3166(2) 0.0548(8) Uani 1 1 d . . . C11 C 0.5098(4) 0.3512(2) 0.4219(3) 0.0432(11) Uani 1 1 d . . . C7 C 0.4680(5) 0.3621(3) 0.7386(4) 0.0502(14) Uani 1 1 d . . . C8 C 0.4816(4) 0.3582(2) 0.6263(3) 0.0436(11) Uani 1 1 d . . . N4 N 0.3919(4) 0.3584(2) 0.9266(3) 0.0555(12) Uani 1 1 d . . . C10 C 0.5772(4) 0.3041(2) 0.5092(4) 0.0451(11) Uani 1 1 d . . . C9 C 0.5649(4) 0.3081(2) 0.6131(3) 0.0459(12) Uani 1 1 d . . . C5 C 0.3650(4) 0.3138(2) 0.7441(3) 0.0394(11) Uani 1 1 d . . . C4 C 0.3324(4) 0.3134(2) 0.8416(3) 0.0418(11) Uani 1 1 d . . . O3 O 0.6530(3) 0.25642(16) 0.4860(2) 0.0602(8) Uani 1 1 d . . . C14 C 0.7243(7) 0.2066(3) 0.5738(7) 0.0694(18) Uani 1 1 d . . . N3 N 0.2468(3) 0.26951(19) 0.8536(3) 0.0461(10) Uani 1 1 d . . . C6 C 0.2974(4) 0.2685(2) 0.6606(4) 0.0458(12) Uani 1 1 d . . . N1 N 0.2069(4) 0.2256(2) 0.6702(3) 0.0476(11) Uani 1 1 d . . . C2 C 0.1856(4) 0.2257(2) 0.7681(4) 0.0460(12) Uani 1 1 d . . . N2 N 0.0979(4) 0.1808(3) 0.7723(4) 0.0643(14) Uani 1 1 d . . . H1 H 0.670(4) 0.176(2) 0.593(3) 0.081(17) Uiso 1 1 d . . . H2 H 0.358(3) 0.4368(14) 0.549(2) 0.014(9) Uiso 1 1 d . . . H3 H 0.252(4) 0.5193(19) 0.287(3) 0.054(14) Uiso 1 1 d . . . H4 H 0.442(3) 0.4066(16) 0.748(2) 0.021(10) Uiso 1 1 d . . . H5 H -0.070(3) 0.1679(14) 0.206(2) 0.012(9) Uiso 1 1 d . . . H6 H 0.308(3) 0.2651(17) 0.596(3) 0.045(12) Uiso 1 1 d . . . H7 H 0.203(4) 0.4739(19) 0.358(3) 0.071(16) Uiso 1 1 d . . . H2W1 H 0.480(3) 0.519(2) 0.050(3) 0.095(18) Uiso 1 1 d D . . H8 H 0.163(3) -0.0390(17) 0.279(3) 0.049(13) Uiso 1 1 d . . . H9 H 0.083(3) -0.0035(16) 0.407(3) 0.042(11) Uiso 1 1 d . . . H10 H 0.541(3) 0.3449(18) 0.798(3) 0.053(14) Uiso 1 1 d . . . H12 H 0.361(4) 0.362(2) 0.981(3) 0.085(17) Uiso 1 1 d . . . H13 H 0.609(3) 0.2711(18) 0.674(3) 0.063(13) Uiso 1 1 d . . . H15 H 0.336(4) 0.528(2) 0.423(3) 0.11(2) Uiso 1 1 d . . . H1W2 H 0.356(4) 0.398(2) 0.177(2) 0.12(2) Uiso 1 1 d D . . H16 H 0.057(3) 0.1501(18) 0.714(3) 0.051(14) Uiso 1 1 d . . . H17 H 0.163(4) 0.1914(18) 0.622(3) 0.046(13) Uiso 1 1 d . . . H18 H 0.769(5) 0.178(2) 0.535(4) 0.14(2) Uiso 1 1 d . . . H2W2 H 0.240(3) 0.430(3) 0.093(4) 0.19(3) Uiso 1 1 d D . . H20 H 0.462(3) 0.3838(19) 0.935(3) 0.044(14) Uiso 1 1 d . . . H21 H -0.069(4) 0.240(2) -0.033(4) 0.13(2) Uiso 1 1 d . . . H22 H 0.077(4) 0.181(3) 0.821(3) 0.09(2) Uiso 1 1 d . . . H23 H 0.114(4) 0.0481(17) 0.031(2) 0.069(15) Uiso 1 1 d D . . H24 H 0.775(5) 0.229(3) 0.634(4) 0.10(3) Uiso 1 1 d . . . H1W1 H 0.368(5) 0.503(3) 0.073(6) 0.34(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 O6 0.114(3) 0.0439(19) 0.0523(18) -0.0056(16) 0.0465(19) 0.0094(19) O8 0.079(3) 0.057(2) 0.0502(19) 0.0185(17) 0.0405(19) 0.0154(19) S 0.0651(9) 0.0532(8) 0.0343(7) -0.0080(6) 0.0269(7) -0.0061(8) O5 0.070(2) 0.078(2) 0.0279(16) -0.0108(16) 0.0144(16) -0.0100(19) C23 0.047(3) 0.049(3) 0.040(3) -0.002(2) 0.022(2) -0.007(3) C22 0.043(3) 0.032(3) 0.047(3) 0.003(3) 0.017(2) 0.001(2) O9 0.082(2) 0.066(2) 0.0477(18) 0.0013(16) 0.0457(18) 0.0002(19) O1W 0.119(4) 0.106(3) 0.110(3) -0.009(3) 0.025(3) -0.030(3) O4 0.066(2) 0.091(2) 0.0585(19) -0.0216(17) 0.0421(17) -0.026(2) C17 0.046(3) 0.038(3) 0.034(2) -0.007(2) 0.021(2) -0.009(2) C21 0.044(3) 0.041(3) 0.027(2) -0.002(2) 0.017(2) -0.004(2) C18 0.052(3) 0.050(3) 0.043(3) -0.004(2) 0.024(3) -0.001(3) C20 0.060(3) 0.057(3) 0.028(3) 0.006(3) 0.022(3) 0.007(3) C16 0.059(4) 0.085(5) 0.055(4) 0.019(4) 0.018(4) 0.019(4) O7 0.080(3) 0.077(2) 0.057(2) 0.008(2) 0.046(2) 0.024(2) C19 0.061(4) 0.043(3) 0.053(3) 0.008(3) 0.022(3) 0.020(3) O1 0.063(2) 0.076(2) 0.0408(19) 0.0100(17) 0.0233(17) 0.0196(19) O2W 0.076(3) 0.111(3) 0.040(2) 0.008(2) 0.0283(19) 0.010(2) C15 0.086(4) 0.125(5) 0.074(3) -0.005(3) 0.057(3) -0.020(4) C12 0.043(3) 0.046(3) 0.039(3) 0.003(2) 0.019(2) 0.000(2) C13 0.045(3) 0.055(3) 0.041(3) -0.003(2) 0.022(3) 0.004(3) O2 0.060(2) 0.073(2) 0.0388(17) -0.0053(15) 0.0278(16) -0.0081(18) C11 0.041(3) 0.057(3) 0.040(3) -0.003(2) 0.025(2) -0.009(2) C7 0.052(4) 0.060(4) 0.042(3) 0.003(3) 0.023(3) 0.008(3) C8 0.049(3) 0.050(3) 0.033(3) 0.002(2) 0.019(2) -0.003(2) N4 0.065(3) 0.066(3) 0.048(3) -0.008(2) 0.036(3) -0.009(2) C10 0.045(3) 0.047(3) 0.052(3) 0.000(3) 0.029(3) -0.001(3) C9 0.049(3) 0.051(3) 0.037(3) 0.006(3) 0.018(3) 0.004(3) C5 0.048(3) 0.045(3) 0.031(2) -0.002(2) 0.021(2) 0.003(2) C4 0.044(3) 0.047(3) 0.028(3) -0.006(2) 0.008(2) 0.008(2) O3 0.067(2) 0.061(2) 0.065(2) 0.0092(18) 0.0391(18) 0.0158(19) C14 0.071(5) 0.055(4) 0.098(6) 0.011(4) 0.051(5) 0.012(4) N3 0.051(3) 0.055(3) 0.034(2) -0.0002(19) 0.020(2) 0.000(2) C6 0.049(3) 0.063(3) 0.035(3) 0.001(3) 0.026(3) -0.002(3) N1 0.054(3) 0.058(3) 0.033(2) -0.010(2) 0.021(2) -0.011(2) C2 0.047(3) 0.056(3) 0.040(3) 0.006(3) 0.023(3) 0.005(3) N2 0.071(4) 0.086(4) 0.046(3) -0.013(3) 0.034(3) -0.028(3) _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 O6 S 1.458(3) . ? O8 C23 1.299(4) . ? S O4 1.448(3) . ? S O5 1.468(3) . ? S C21 1.785(3) . ? C23 O9 1.224(4) . ? C23 C17 1.490(5) . ? C22 C21 1.371(4) . ? C22 C17 1.401(5) . ? C17 C18 1.382(5) . ? C21 C20 1.372(5) . ? C18 O7 1.365(4) . ? C18 C19 1.398(5) . ? C20 C19 1.389(5) . ? C16 O1 1.421(6) . ? O1 C12 1.374(4) . ? C15 O2 1.418(4) . ? C12 C11 1.377(5) . ? C12 C13 1.386(4) . ? C13 C8 1.388(5) . ? O2 C11 1.399(4) . ? C11 C10 1.385(5) . ? C7 C8 1.507(5) . ? C7 C5 1.511(6) . ? C8 C9 1.396(5) . ? N4 C4 1.323(5) . ? C10 O3 1.360(4) . ? C10 C9 1.394(5) . ? C5 C6 1.336(5) . ? C5 C4 1.440(5) . ? C4 N3 1.337(5) . ? O3 C14 1.431(6) . ? N3 C2 1.316(5) . ? C6 N1 1.357(5) . ? N1 C2 1.370(4) . ? C2 N2 1.328(5) . ? 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 O4 S O6 113.80(19) . . ? O4 S O5 111.13(16) . . ? O6 S O5 112.43(17) . . ? O4 S C21 107.96(16) . . ? O6 S C21 104.60(17) . . ? O5 S C21 106.32(18) . . ? O9 C23 O8 124.3(4) . . ? O9 C23 C17 122.0(4) . . ? O8 C23 C17 113.7(4) . . ? C21 C22 C17 120.5(4) . . ? C18 C17 C22 119.2(4) . . ? C18 C17 C23 121.1(4) . . ? C22 C17 C23 119.7(4) . . ? C22 C21 C20 120.9(4) . . ? C22 C21 S 118.8(3) . . ? C20 C21 S 120.3(3) . . ? O7 C18 C17 122.7(4) . . ? O7 C18 C19 117.8(4) . . ? C17 C18 C19 119.5(4) . . ? C21 C20 C19 119.1(4) . . ? C20 C19 C18 120.8(4) . . ? C12 O1 C16 117.6(4) . . ? O1 C12 C11 115.3(4) . . ? O1 C12 C13 124.1(4) . . ? C11 C12 C13 120.6(4) . . ? C12 C13 C8 119.2(4) . . ? C11 O2 C15 113.0(3) . . ? C12 C11 C10 120.6(4) . . ? C12 C11 O2 119.0(4) . . ? C10 C11 O2 120.3(4) . . ? C8 C7 C5 113.7(4) . . ? C13 C8 C9 120.6(4) . . ? C13 C8 C7 120.1(4) . . ? C9 C8 C7 119.3(4) . . ? O3 C10 C11 116.0(4) . . ? O3 C10 C9 124.4(4) . . ? C11 C10 C9 119.5(4) . . ? C10 C9 C8 119.5(4) . . ? C6 C5 C4 114.7(4) . . ? C6 C5 C7 123.5(4) . . ? C4 C5 C7 121.8(4) . . ? N4 C4 N3 117.0(4) . . ? N4 C4 C5 118.7(4) . . ? N3 C4 C5 124.3(4) . . ? C10 O3 C14 117.9(4) . . ? C2 N3 C4 117.1(4) . . ? C5 C6 N1 121.3(4) . . ? C6 N1 C2 120.6(4) . . ? N3 C2 N2 121.1(4) . . ? N3 C2 N1 121.8(4) . . ? N2 C2 N1 117.1(5) . . ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 0.213 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.042 #==============================================================================