Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Kidowaki, Masatoshi' ; Institute for Material and Chemical Process National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 5, Higashi 1-1-1, Tsukuba Ibaraki Japan 305-8565 ; 'Tamaoki, Nobuyuki' ; Institute for Material and Chemical Process National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 5, Higashi 1-1-1, Tsukuba Ibaraki Japan 305-8565 ; #------------------------------------------------------------------------------- # SUBMISSION DETAILS _publ_contact_author ; Dr. Nobuyuki Tamaoki Institute for Material and Chemical Process National Institute of Advanced Industrial Science and Technology (AIST) Tsukuba Central 5, Higashi 1-1-1, Tsukuba Ibaraki Japan 305-8565 ; _publ_contact_author_email n.tamaoki@aist.go.jp _publ_contact_author_fax +81-298-61-4673 _publ_contact_author_phone +81-298-61-4671 _publ_requested_journal 'Chemical Communications' #------------------------------------------------------------------------------- # TITLE AND AUTHOR LIST _publ_section_title ; Unique crystal structure of donor acceptor complex: crossed arrangement of two charge-transfer columns ; #------------------------------------------------------------------------------- data_C3 _database_code_CSD 191673 #------------------------------------------------------------------------------- #------------------------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C38 H36 N2 O14 S2 ' _chemical_formula_moiety 'C14 H6 O8 S2, C12 H14 N2, 2(C6 H4 O2), 2(H2 O)' _chemical_formula_weight 808.83 _chemical_melting_point ? 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 C C 0.0033 0.0016 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 H H 0.0000 0.0000 International Tables Vol C Tables 4.2.6.8 and 6.1.1.4 #------------------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 c 1' _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,1/2+z _cell_length_a 7.830(2) _cell_length_b 11.920(3) _cell_length_c 20.356(3) _cell_angle_alpha 90 _cell_angle_beta 101.77(2) _cell_angle_gamma 90 _cell_volume 1859.9(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.2 _cell_measurement_theta_max 11.4 _cell_measurement_temperature 223.2 _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _exptl_crystal_F_000 840 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5232 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.92 _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 ? #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). H atoms attached to oxygen of phenol were omitted, because they were not observed to D-fourier map. The hydrogen atoms of waters were found in D-fourier map and refined riding on their carrier oxygen atoms by using 0.96 for OH distance and 1.5 for H---H distance to a tolerance of plus or minus 0.04. ; _reflns_number_total 4592 _reflns_number_gt 1752 _reflns_threshold_expression >2.0sigma(I) _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 and d-fourier' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack ,but not accurately' _refine_ls_abs_structure_Flack -0.04(19) _refine_ls_number_reflns 4592 _refine_ls_number_parameters 517 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1336 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.2019 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.847 _refine_ls_shift/su_max 0.028 _refine_diff_density_max 0.364 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.080 #------------------------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.5862(3) 0.4117(2) 0.47064(14) 0.0299(6) Uani 1 1 d . . . S2 S 0.0674(3) -0.1747(2) 0.36689(13) 0.0305(6) Uani 1 1 d . . . O1 O 0.6425(10) 0.4618(6) 0.4135(4) 0.0362(19) Uani 1 1 d . . . O2 O 0.5572(10) 0.4972(7) 0.5194(4) 0.042(2) Uani 1 1 d . . . O3 O 0.6960(10) 0.3206(6) 0.5027(4) 0.0377(18) Uani 1 1 d . . . O4 O -0.0112(10) -0.1104(6) 0.4122(3) 0.0357(18) Uani 1 1 d . . . O5 O -0.0387(9) -0.1858(6) 0.2991(3) 0.0379(19) Uani 1 1 d . . . O6 O 0.1281(10) -0.2860(6) 0.3937(4) 0.040(2) Uani 1 1 d . . . O7 O -0.0100(9) 0.0726(6) 0.3296(4) 0.0358(18) Uani 1 1 d . . . O8 O 0.6120(10) 0.2264(6) 0.3703(4) 0.0385(19) Uani 1 1 d . . . O9 O 0.5962(14) 0.2579(6) 0.6173(4) 0.060(3) Uani 1 1 d . . . O10 O 0.3514(14) -0.1774(7) 0.6100(5) 0.063(3) Uani 1 1 d . . . O11 O 1.2680(14) -0.2706(7) 0.7214(5) 0.066(3) Uani 1 1 d . . . O12 O 1.0856(15) -0.7196(7) 0.6981(5) 0.072(3) Uani 1 1 d . . . O13 O 0.9019(17) -0.3746(9) 0.4770(5) 0.086(3) Uani 1 1 d D . . O14 O 0.3997(15) -0.2963(7) 0.5081(5) 0.067(3) Uani 1 1 d D . . N1 N 0.9569(13) 0.0130(9) 0.5911(5) 0.046(3) Uani 1 1 d . . . N2 N 0.6883(14) -0.4755(8) 0.7318(5) 0.043(3) Uani 1 1 d . . . C1 C 0.3748(14) 0.3499(8) 0.4430(5) 0.032(3) Uani 1 1 d . . . C2 C 0.2373(16) 0.4037(9) 0.4599(6) 0.038(3) Uani 1 1 d . . . C3 C 0.0663(15) 0.3632(9) 0.4445(6) 0.036(3) Uani 1 1 d . . . C4 C 0.0379(13) 0.2609(8) 0.4115(5) 0.030(2) Uani 1 1 d . . . C5 C 0.1759(13) 0.2040(9) 0.3946(5) 0.030(2) Uani 1 1 d . . . C6 C 0.1356(13) 0.0919(8) 0.3598(5) 0.026(2) Uani 1 1 d . . . C7 C 0.2830(13) 0.0133(8) 0.3641(5) 0.025(2) Uani 1 1 d . . . C8 C 0.2623(14) -0.1051(9) 0.3583(5) 0.031(2) Uani 1 1 d . . . C9 C 0.4095(14) -0.1704(9) 0.3565(6) 0.033(3) Uani 1 1 d . . . C10 C 0.5685(16) -0.1234(9) 0.3570(7) 0.047(3) Uani 1 1 d . . . C11 C 0.5902(14) -0.0079(9) 0.3635(6) 0.034(3) Uani 1 1 d . . . C12 C 0.4494(13) 0.0574(8) 0.3689(5) 0.026(2) Uani 1 1 d . . . C13 C 0.4811(12) 0.1832(8) 0.3813(5) 0.024(2) Uani 1 1 d . . . C14 C 0.3465(13) 0.2466(8) 0.4071(5) 0.024(2) Uani 1 1 d . . . C15 C 0.944(2) -0.0856(12) 0.5584(7) 0.065(4) Uani 1 1 d . . . C16 C 0.891(2) -0.1795(11) 0.5846(6) 0.056(4) Uani 1 1 d . . . C17 C 0.8479(14) -0.1786(10) 0.6475(5) 0.032(2) Uani 1 1 d . . . C18 C 0.8554(16) -0.0753(10) 0.6790(5) 0.040(3) Uani 1 1 d . . . C19 C 0.9110(17) 0.0187(11) 0.6526(6) 0.048(3) Uani 1 1 d . . . C20 C 1.014(2) 0.1183(12) 0.5621(7) 0.067(5) Uani 1 1 d . . . C21 C 0.7895(15) -0.2797(9) 0.6756(5) 0.034(3) Uani 1 1 d . . . C22 C 0.7737(18) -0.3837(10) 0.6396(5) 0.045(3) Uani 1 1 d . . . C23 C 0.7256(18) -0.4781(11) 0.6698(6) 0.049(3) Uani 1 1 d . . . C24 C 0.7023(17) -0.3807(10) 0.7667(6) 0.044(3) Uani 1 1 d . . . C25 C 0.7517(16) -0.2843(9) 0.7398(5) 0.039(3) Uani 1 1 d . . . C26 C 0.6362(19) -0.5802(10) 0.7614(7) 0.053(4) Uani 1 1 d . . . C27 C 0.5311(17) 0.1524(10) 0.6135(6) 0.043(3) Uani 1 1 d . . . C28 C 0.5273(14) 0.0872(10) 0.5582(5) 0.035(3) Uani 1 1 d . . . C29 C 0.4665(16) -0.0260(9) 0.5547(5) 0.035(3) Uani 1 1 d . . . C30 C 0.4120(15) -0.0701(9) 0.6095(6) 0.038(3) Uani 1 1 d . . . C31 C 0.4088(18) -0.0024(11) 0.6655(6) 0.050(3) Uani 1 1 d . . . C32 C 0.469(2) 0.1071(10) 0.6660(6) 0.055(4) Uani 1 1 d . . . C33 C 1.2262(17) -0.3813(10) 0.7146(6) 0.044(3) Uani 1 1 d . . . C34 C 1.227(2) -0.4404(11) 0.6567(6) 0.052(4) Uani 1 1 d . . . C35 C 1.180(2) -0.5536(11) 0.6507(6) 0.060(4) Uani 1 1 d . . . C36 C 1.135(2) -0.6086(11) 0.7049(6) 0.054(4) Uani 1 1 d . . . C37 C 1.1363(18) -0.5491(11) 0.7630(6) 0.050(4) Uani 1 1 d . . . C38 C 1.1828(17) -0.4367(10) 0.7682(6) 0.043(3) Uani 1 1 d . . . H1 H 0.2507 0.4726 0.4810 0.043 Uiso 1 1 d . . . H2 H -0.0346 0.4048 0.4532 0.042 Uiso 1 1 d . . . H3 H -0.0851 0.2324 0.3976 0.035 Uiso 1 1 d . . . H4 H 0.3894 -0.2487 0.3517 0.038 Uiso 1 1 d . . . H5 H 0.6589 -0.1709 0.3514 0.058 Uiso 1 1 d . . . H6 H 0.6941 0.0274 0.3623 0.043 Uiso 1 1 d . . . H7 H 0.9711 -0.0878 0.5143 0.073 Uiso 1 1 d . . . H8 H 0.8809 -0.2475 0.5592 0.066 Uiso 1 1 d . . . H9 H 0.8137 -0.0688 0.7188 0.052 Uiso 1 1 d . . . H10 H 0.9127 0.0892 0.6733 0.056 Uiso 1 1 d . . . H11 H 0.7915 -0.3852 0.5934 0.057 Uiso 1 1 d . . . H12 H 0.7093 -0.5486 0.6435 0.061 Uiso 1 1 d . . . H13 H 0.6749 -0.3789 0.8092 0.052 Uiso 1 1 d . . . H14 H 0.7563 -0.2164 0.7643 0.047 Uiso 1 1 d . . . H15 H 0.5560 0.1177 0.5173 0.038 Uiso 1 1 d . . . H16 H 0.4561 -0.0703 0.5132 0.048 Uiso 1 1 d . . . H17 H 0.3582 -0.0317 0.7000 0.060 Uiso 1 1 d . . . H18 H 0.4596 0.1520 0.7016 0.067 Uiso 1 1 d . . . H19 H 1.2489 -0.4012 0.6173 0.065 Uiso 1 1 d . . . H20 H 1.1731 -0.5926 0.6080 0.074 Uiso 1 1 d . . . H21 H 1.0972 -0.5848 0.7978 0.056 Uiso 1 1 d . . . H22 H 1.1742 -0.3945 0.8062 0.058 Uiso 1 1 d . . . H23 H 1.1062 0.1501 0.5889 0.077 Uiso 1 1 d . . . H24 H 1.0339 0.1050 0.5171 0.077 Uiso 1 1 d . . . H25 H 0.9144 0.1742 0.5540 0.077 Uiso 1 1 d . . . H26 H 0.6054 -0.5686 0.8032 0.062 Uiso 1 1 d . . . H27 H 0.5252 -0.6123 0.7317 0.062 Uiso 1 1 d . . . H28 H 0.7192 -0.6368 0.7633 0.062 Uiso 1 1 d . . . H29 H 0.816(4) -0.316(7) 0.472(4) 0.098 Uiso 1 1 d D . . H30 H 0.925(7) -0.393(8) 0.524(4) 0.098 Uiso 1 1 d D . . H31 H 0.386(7) -0.360(8) 0.534(6) 0.098 Uiso 1 1 d D . . H32 H 0.282(9) -0.287(11) 0.480(7) 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 0.0276(15) 0.0278(14) 0.0341(14) -0.0034(13) 0.0062(12) -0.0067(13) S2 0.0270(15) 0.0321(15) 0.0335(14) -0.0058(13) 0.0089(12) -0.0037(13) O1 0.037(5) 0.028(4) 0.041(4) -0.001(4) 0.004(4) -0.012(4) O2 0.039(5) 0.041(5) 0.041(5) -0.016(4) -0.005(4) -0.006(4) O3 0.032(4) 0.033(4) 0.042(4) 0.004(4) -0.007(4) 0.007(4) O4 0.038(4) 0.045(5) 0.031(4) -0.005(4) 0.023(3) 0.002(4) O5 0.029(4) 0.045(5) 0.036(4) -0.018(4) -0.002(3) -0.007(4) O6 0.038(5) 0.023(4) 0.059(5) 0.006(3) 0.008(4) 0.000(4) O7 0.020(4) 0.041(4) 0.042(4) -0.007(4) -0.004(3) -0.003(4) O8 0.030(4) 0.037(4) 0.054(5) 0.000(4) 0.021(4) -0.006(4) O9 0.100(8) 0.036(5) 0.044(5) -0.019(4) 0.019(5) -0.023(5) O10 0.092(7) 0.020(4) 0.077(7) 0.008(4) 0.018(6) -0.014(5) O11 0.091(8) 0.042(5) 0.059(6) 0.000(4) 0.005(6) -0.020(5) O12 0.130(10) 0.031(5) 0.061(6) -0.011(4) 0.036(6) -0.023(6) O13 0.115(9) 0.069(7) 0.087(7) -0.036(6) 0.056(7) -0.042(7) O14 0.094(8) 0.037(5) 0.060(6) -0.003(4) -0.008(6) 0.011(5) N1 0.044(7) 0.052(7) 0.044(6) 0.007(5) 0.012(5) -0.002(6) N2 0.043(6) 0.039(6) 0.045(6) -0.007(5) 0.006(5) -0.011(5) C1 0.035(6) 0.026(6) 0.033(6) 0.002(5) 0.004(5) 0.004(5) C2 0.042(8) 0.028(6) 0.047(7) -0.004(5) 0.016(6) -0.002(6) C3 0.029(7) 0.030(6) 0.056(7) -0.005(5) 0.023(6) 0.004(5) C4 0.021(6) 0.032(6) 0.037(6) 0.004(5) 0.010(5) -0.005(5) C5 0.026(6) 0.037(6) 0.026(5) 0.010(5) 0.005(5) 0.010(5) C6 0.026(5) 0.024(5) 0.028(5) 0.014(4) 0.006(5) 0.007(5) C7 0.024(5) 0.031(6) 0.020(5) 0.001(4) 0.003(4) -0.007(5) C8 0.028(6) 0.034(6) 0.032(6) -0.011(5) 0.010(5) -0.014(5) C9 0.022(6) 0.033(6) 0.047(7) -0.005(5) 0.013(5) -0.001(5) C10 0.032(7) 0.035(6) 0.073(9) -0.011(6) 0.010(6) -0.003(6) C11 0.026(6) 0.035(6) 0.044(6) -0.007(6) 0.012(5) 0.000(5) C12 0.019(5) 0.033(6) 0.024(5) -0.008(4) 0.001(4) 0.006(5) C13 0.021(5) 0.029(6) 0.023(5) -0.002(4) 0.004(4) 0.006(5) C14 0.017(5) 0.028(5) 0.023(5) 0.004(4) -0.006(4) 0.000(4) C15 0.097(13) 0.052(8) 0.052(8) 0.000(7) 0.030(9) 0.010(9) C16 0.090(11) 0.039(8) 0.046(8) 0.002(6) 0.035(8) -0.004(8) C17 0.025(5) 0.040(6) 0.032(6) -0.014(5) 0.007(5) 0.006(5) C18 0.045(7) 0.036(7) 0.034(6) 0.001(5) -0.002(6) -0.005(6) C19 0.050(8) 0.052(8) 0.041(7) -0.004(6) 0.007(6) 0.005(7) C20 0.083(12) 0.067(10) 0.054(8) 0.026(8) 0.017(8) -0.006(9) C21 0.034(7) 0.034(6) 0.034(6) -0.006(5) 0.008(5) 0.002(5) C22 0.072(9) 0.051(8) 0.011(5) -0.013(5) 0.004(6) -0.010(7) C23 0.064(9) 0.054(8) 0.026(6) -0.023(6) 0.002(6) -0.001(7) C24 0.054(8) 0.043(7) 0.035(7) 0.007(6) 0.012(6) -0.005(6) C25 0.062(9) 0.026(6) 0.032(6) -0.009(5) 0.020(6) 0.001(6) C26 0.069(10) 0.031(7) 0.064(9) 0.009(6) 0.022(7) 0.004(7) C27 0.038(7) 0.046(8) 0.042(7) 0.005(6) 0.002(6) -0.002(6) C28 0.034(6) 0.043(7) 0.027(5) 0.014(5) 0.007(5) 0.007(6) C29 0.052(8) 0.027(6) 0.031(6) -0.004(5) 0.019(6) -0.006(6) C30 0.038(7) 0.034(7) 0.042(7) 0.020(5) 0.011(6) 0.005(5) C31 0.062(9) 0.062(8) 0.032(6) 0.001(6) 0.019(6) -0.020(8) C32 0.095(12) 0.037(7) 0.039(7) -0.004(6) 0.031(8) 0.001(7) C33 0.037(7) 0.039(7) 0.052(8) -0.005(6) -0.003(6) -0.009(6) C34 0.075(10) 0.050(8) 0.032(6) 0.005(6) 0.017(7) 0.002(7) C35 0.108(13) 0.046(8) 0.035(7) 0.000(6) 0.031(8) -0.011(8) C36 0.086(11) 0.049(9) 0.034(7) 0.005(6) 0.031(7) 0.006(8) C37 0.052(9) 0.059(9) 0.037(7) 0.011(6) 0.003(6) -0.003(7) C38 0.055(8) 0.037(7) 0.037(6) 0.011(5) 0.005(6) -0.016(6) #------------------------------------------------------------------------------- # MOLCULAR GEOMETRY _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 O1 1.454(8) . ? S1 O3 1.455(7) . ? S1 O2 1.472(8) . ? S1 C1 1.794(11) . ? S2 O4 1.431(7) . ? S2 O5 1.464(7) . ? S2 O6 1.476(7) . ? S2 C8 1.777(11) . ? O7 C6 1.202(12) . ? O8 C13 1.209(12) . ? O9 C27 1.353(13) . ? O10 C30 1.365(13) . ? O11 C33 1.359(13) . ? O12 C36 1.378(15) . ? O13 H29 0.96(4) . ? O13 H30 0.96(8) . ? O14 H31 0.95(9) . ? O14 H32 0.99(5) . ? N1 C15 1.345(17) . ? N1 C19 1.372(15) . ? N1 C20 1.496(17) . ? N2 C24 1.327(14) . ? N2 C23 1.354(15) . ? N2 C26 1.478(15) . ? C1 C2 1.357(15) . ? C1 C14 1.426(14) . ? C2 C3 1.398(16) . ? C2 H1 0.922 . ? C3 C4 1.387(15) . ? C3 H2 0.979 . ? C4 C5 1.378(14) . ? C4 H3 1.006 . ? C5 C14 1.404(14) . ? C5 C6 1.515(15) . ? C6 C7 1.476(14) . ? C7 C12 1.390(14) . ? C7 C8 1.422(14) . ? C8 C9 1.397(15) . ? C9 C10 1.364(16) . ? C9 H4 0.948 . ? C10 C11 1.389(15) . ? C10 H5 0.932 . ? C11 C12 1.372(14) . ? C11 H6 0.921 . ? C12 C13 1.532(14) . ? C13 C14 1.477(14) . ? C15 C16 1.341(18) . ? C15 H7 0.964 . ? C16 C17 1.390(15) . ? C16 H8 0.956 . ? C17 C18 1.384(15) . ? C17 C21 1.447(16) . ? C18 C19 1.353(17) . ? C18 H9 0.936 . ? C19 H10 0.940 . ? C20 H23 0.893 . ? C20 H24 0.972 . ? C20 H25 1.015 . ? C21 C25 1.400(15) . ? C21 C22 1.433(15) . ? C22 C23 1.371(17) . ? C22 H11 0.979 . ? C23 H12 0.990 . ? C24 C25 1.361(15) . ? C24 H13 0.934 . ? C25 H14 0.947 . ? C26 H26 0.940 . ? C26 H27 1.025 . ? C26 H28 0.932 . ? C27 C28 1.363(16) . ? C27 C32 1.371(17) . ? C28 C29 1.427(15) . ? C28 H15 0.976 . ? C29 C30 1.377(15) . ? C29 H16 0.985 . ? C30 C31 1.401(17) . ? C31 C32 1.387(17) . ? C31 H17 0.941 . ? C32 H18 0.916 . ? C33 C34 1.374(17) . ? C33 C38 1.376(16) . ? C34 C35 1.397(17) . ? C34 H19 0.974 . ? C35 C36 1.390(16) . ? C35 H20 0.976 . ? C36 C37 1.378(17) . ? C37 C38 1.387(16) . ? C37 H21 0.930 . ? C38 H22 0.937 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O3 114.7(5) . . ? O1 S1 O2 111.7(5) . . ? O3 S1 O2 111.9(5) . . ? O1 S1 C1 109.2(5) . . ? O3 S1 C1 104.9(5) . . ? O2 S1 C1 103.7(5) . . ? O4 S2 O5 114.8(4) . . ? O4 S2 O6 113.1(5) . . ? O5 S2 O6 110.2(4) . . ? O4 S2 C8 107.7(5) . . ? O5 S2 C8 106.4(5) . . ? O6 S2 C8 103.8(5) . . ? H29 O13 H30 105(5) . . ? H31 O14 H32 103(6) . . ? C15 N1 C19 119.2(12) . . ? C15 N1 C20 122.4(11) . . ? C19 N1 C20 118.3(11) . . ? C24 N2 C23 120.5(11) . . ? C24 N2 C26 120.1(10) . . ? C23 N2 C26 119.4(10) . . ? C2 C1 C14 119.4(10) . . ? C2 C1 S1 117.1(8) . . ? C14 C1 S1 123.5(8) . . ? C1 C2 C3 123.5(10) . . ? C1 C2 H1 121.2 . . ? C3 C2 H1 115.2 . . ? C4 C3 C2 117.7(10) . . ? C4 C3 H2 118.5 . . ? C2 C3 H2 123.7 . . ? C5 C4 C3 119.8(10) . . ? C5 C4 H3 121.2 . . ? C3 C4 H3 118.9 . . ? C4 C5 C14 122.9(10) . . ? C4 C5 C6 116.9(9) . . ? C14 C5 C6 120.3(9) . . ? O7 C6 C7 123.9(10) . . ? O7 C6 C5 119.6(9) . . ? C7 C6 C5 116.5(9) . . ? C12 C7 C8 118.1(9) . . ? C12 C7 C6 118.3(9) . . ? C8 C7 C6 123.4(10) . . ? C9 C8 C7 118.3(10) . . ? C9 C8 S2 118.1(8) . . ? C7 C8 S2 122.7(8) . . ? C10 C9 C8 121.8(10) . . ? C10 C9 H4 122.5 . . ? C8 C9 H4 115.5 . . ? C9 C10 C11 120.1(11) . . ? C9 C10 H5 117.7 . . ? C11 C10 H5 122.2 . . ? C12 C11 C10 119.0(11) . . ? C12 C11 H6 118.1 . . ? C10 C11 H6 122.8 . . ? C11 C12 C7 122.4(9) . . ? C11 C12 C13 117.6(9) . . ? C7 C12 C13 120.0(9) . . ? O8 C13 C14 122.8(9) . . ? O8 C13 C12 120.1(9) . . ? C14 C13 C12 117.2(8) . . ? C5 C14 C1 116.6(9) . . ? C5 C14 C13 118.1(9) . . ? C1 C14 C13 125.2(9) . . ? N1 C15 C16 122.0(12) . . ? N1 C15 H7 118.5 . . ? C16 C15 H7 119.5 . . ? C15 C16 C17 120.9(12) . . ? C15 C16 H8 119.5 . . ? C17 C16 H8 119.6 . . ? C18 C17 C16 116.0(11) . . ? C18 C17 C21 123.0(9) . . ? C16 C17 C21 120.9(10) . . ? C19 C18 C17 122.6(11) . . ? C19 C18 H9 118.2 . . ? C17 C18 H9 119.1 . . ? C18 C19 N1 119.1(12) . . ? C18 C19 H10 122.6(13) . . ? N1 C19 H10 118.1 . . ? N1 C20 H23 112.7 . . ? N1 C20 H24 110.7 . . ? H23 C20 H24 112.5 . . ? N1 C20 H25 109.3 . . ? H23 C20 H25 108.6 . . ? H24 C20 H25 102.6 . . ? C25 C21 C22 115.5(10) . . ? C25 C21 C17 123.1(9) . . ? C22 C21 C17 121.3(10) . . ? C23 C22 C21 119.0(9) . . ? C23 C22 H11 121.4 . . ? C21 C22 H11 119.5 . . ? N2 C23 C22 122.0(10) . . ? N2 C23 H12 119.7 . . ? C22 C23 H12 118.1 . . ? N2 C24 C25 120.2(10) . . ? N2 C24 H13 120.3 . . ? C25 C24 H13 119.5 . . ? C24 C25 C21 122.7(10) . . ? C24 C25 H14 119.6 . . ? C21 C25 H14 117.7 . . ? N2 C26 H26 112.8 . . ? N2 C26 H27 110.3 . . ? H26 C26 H27 104.1 . . ? N2 C26 H28 112.4 . . ? H26 C26 H28 111.9 . . ? H27 C26 H28 104.7 . . ? O9 C27 C28 121.5(11) . . ? O9 C27 C32 120.7(12) . . ? C28 C27 C32 117.9(11) . . ? C27 C28 C29 122.1(10) . . ? C27 C28 H15 121.5 . . ? C29 C28 H15 116.3 . . ? C30 C29 C28 118.4(10) . . ? C30 C29 H16 120.3 . . ? C28 C29 H16 121.2 . . ? O10 C30 C29 121.9(11) . . ? O10 C30 C31 118.0(10) . . ? C29 C30 C31 119.9(11) . . ? C32 C31 C30 119.0(11) . . ? C32 C31 H17 122.7 . . ? C30 C31 H17 118.2 . . ? C27 C32 C31 122.6(11) . . ? C27 C32 H18 119.0 . . ? C31 C32 H18 118.2 . . ? O11 C33 C34 122.9(12) . . ? O11 C33 C38 118.6(11) . . ? C34 C33 C38 118.6(11) . . ? C33 C34 C35 121.7(11) . . ? C33 C34 H19 119.5 . . ? C35 C34 H19 118.6 . . ? C36 C35 C34 119.3(11) . . ? C36 C35 H20 120.2 . . ? C34 C35 H20 120.3 . . ? C37 C36 O12 122.3(11) . . ? C37 C36 C35 118.7(12) . . ? O12 C36 C35 119.0(11) . . ? C36 C37 C38 121.2(12) . . ? C36 C37 H21 118.2 . . ? C38 C37 H21 120.5 . . ? C33 C38 C37 120.5(12) . . ? C33 C38 H22 117.9 . . ? C37 C38 H22 121.3 . . ? 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 S1 C1 C2 -107.0(9) . . . . ? O3 S1 C1 C2 129.7(9) . . . . ? O2 S1 C1 C2 12.2(10) . . . . ? O1 S1 C1 C14 75.6(9) . . . . ? O3 S1 C1 C14 -47.8(9) . . . . ? O2 S1 C1 C14 -165.3(8) . . . . ? C14 C1 C2 C3 0.4(17) . . . . ? S1 C1 C2 C3 -177.1(9) . . . . ? C1 C2 C3 C4 1.7(17) . . . . ? C2 C3 C4 C5 -0.7(16) . . . . ? C3 C4 C5 C14 -2.3(16) . . . . ? C3 C4 C5 C6 178.9(9) . . . . ? C4 C5 C6 O7 23.6(14) . . . . ? C14 C5 C6 O7 -155.2(10) . . . . ? C4 C5 C6 C7 -158.0(9) . . . . ? C14 C5 C6 C7 23.2(13) . . . . ? O7 C6 C7 C12 148.2(10) . . . . ? C5 C6 C7 C12 -30.1(13) . . . . ? O7 C6 C7 C8 -26.7(16) . . . . ? C5 C6 C7 C8 155.0(9) . . . . ? C12 C7 C8 C9 -1.0(15) . . . . ? C6 C7 C8 C9 173.9(9) . . . . ? C12 C7 C8 S2 168.3(7) . . . . ? C6 C7 C8 S2 -16.7(15) . . . . ? O4 S2 C8 C9 139.3(9) . . . . ? O5 S2 C8 C9 -97.2(9) . . . . ? O6 S2 C8 C9 19.1(10) . . . . ? O4 S2 C8 C7 -30.1(10) . . . . ? O5 S2 C8 C7 93.4(9) . . . . ? O6 S2 C8 C7 -150.3(9) . . . . ? C7 C8 C9 C10 -3.3(17) . . . . ? S2 C8 C9 C10 -173.1(10) . . . . ? C8 C9 C10 C11 4(2) . . . . ? C9 C10 C11 C12 -1(2) . . . . ? C10 C11 C12 C7 -3.8(18) . . . . ? C10 C11 C12 C13 175.5(10) . . . . ? C8 C7 C12 C11 4.6(15) . . . . ? C6 C7 C12 C11 -170.6(10) . . . . ? C8 C7 C12 C13 -174.7(9) . . . . ? C6 C7 C12 C13 10.1(14) . . . . ? C11 C12 C13 O8 17.8(15) . . . . ? C7 C12 C13 O8 -162.9(9) . . . . ? C11 C12 C13 C14 -162.0(9) . . . . ? C7 C12 C13 C14 17.3(13) . . . . ? C4 C5 C14 C1 4.3(14) . . . . ? C6 C5 C14 C1 -177.0(9) . . . . ? C4 C5 C14 C13 -174.6(10) . . . . ? C6 C5 C14 C13 4.2(13) . . . . ? C2 C1 C14 C5 -3.3(14) . . . . ? S1 C1 C14 C5 174.1(7) . . . . ? C2 C1 C14 C13 175.5(10) . . . . ? S1 C1 C14 C13 -7.2(14) . . . . ? O8 C13 C14 C5 156.0(10) . . . . ? C12 C13 C14 C5 -24.2(12) . . . . ? O8 C13 C14 C1 -22.7(15) . . . . ? C12 C13 C14 C1 157.1(9) . . . . ? C19 N1 C15 C16 -1(2) . . . . ? C20 N1 C15 C16 -179.4(14) . . . . ? N1 C15 C16 C17 0(2) . . . . ? C15 C16 C17 C18 3(2) . . . . ? C15 C16 C17 C21 179.6(14) . . . . ? C16 C17 C18 C19 -3.8(18) . . . . ? C21 C17 C18 C19 179.7(11) . . . . ? C17 C18 C19 N1 2.1(19) . . . . ? C15 N1 C19 C18 0.5(19) . . . . ? C20 N1 C19 C18 178.7(12) . . . . ? C18 C17 C21 C25 -6.4(18) . . . . ? C16 C17 C21 C25 177.2(13) . . . . ? C18 C17 C21 C22 176.2(12) . . . . ? C16 C17 C21 C22 -0.2(17) . . . . ? C25 C21 C22 C23 -0.5(18) . . . . ? C17 C21 C22 C23 177.0(12) . . . . ? C24 N2 C23 C22 -2(2) . . . . ? C26 N2 C23 C22 179.6(12) . . . . ? C21 C22 C23 N2 2(2) . . . . ? C23 N2 C24 C25 1(2) . . . . ? C26 N2 C24 C25 179.5(12) . . . . ? N2 C24 C25 C21 0(2) . . . . ? C22 C21 C25 C24 -0.3(18) . . . . ? C17 C21 C25 C24 -177.8(11) . . . . ? O9 C27 C28 C29 177.1(11) . . . . ? C32 C27 C28 C29 -1.9(19) . . . . ? C27 C28 C29 C30 -0.7(18) . . . . ? C28 C29 C30 O10 179.7(11) . . . . ? C28 C29 C30 C31 3.3(18) . . . . ? O10 C30 C31 C32 -179.7(13) . . . . ? C29 C30 C31 C32 -3(2) . . . . ? O9 C27 C32 C31 -176.9(14) . . . . ? C28 C27 C32 C31 2(2) . . . . ? C30 C31 C32 C27 0(2) . . . . ? O11 C33 C34 C35 -178.9(14) . . . . ? C38 C33 C34 C35 2(2) . . . . ? C33 C34 C35 C36 -1(2) . . . . ? C34 C35 C36 C37 1(2) . . . . ? C34 C35 C36 O12 178.4(14) . . . . ? O12 C36 C37 C38 -178.4(13) . . . . ? C35 C36 C37 C38 -1(2) . . . . ? O11 C33 C38 C37 178.9(13) . . . . ? C34 C33 C38 C37 -2(2) . . . . ? C36 C37 C38 C33 1(2) . . . . ? #------------------------------------------------------- data_c2 database_code_CSD 191674 #------------------------------------------------------------------------------- #------------------------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C58 H46 N4 O18 S4 ' _chemical_formula_moiety ? _chemical_formula_weight 1215.26 _chemical_melting_point ? 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 C C 0.0033 0.0016 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 H H 0.0000 0.0000 International Tables Vol C Tables 4.2.6.8 and 6.1.1.4 #---------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 6.866(1) _cell_length_b 10.475(2) _cell_length_c 18.808(4) _cell_angle_alpha 75.84(1) _cell_angle_beta 84.34(1) _cell_angle_gamma 86.28(1) _cell_volume 1304.2(5) _cell_formula_units_Z 1 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 17.9 _cell_measurement_theta_max 26.2 _cell_measurement_temperature 296.2 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.020 _exptl_crystal_F_000 630.0 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 2.400 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.998 #------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w _diffrn_reflns_number 5044 _diffrn_reflns_av_R_equivalents 0.008 _diffrn_reflns_theta_max 69.93 _diffrn_measured_fraction_theta_max 0.9933 _diffrn_reflns_theta_full 69.93 _diffrn_measured_fraction_theta_full 0.9933 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.05 _computing_data_collection . _computing_cell_refinement . _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #--------------------------------------------------------------- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4895 _reflns_number_gt 4547 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1742 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 4895 _refine_ls_number_parameters 379 _refine_ls_goodness_of_fit_ref 2.238 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.06600(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0148 _refine_diff_density_max 0.35 _refine_diff_density_min -0.75 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? #----------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S 0.70843(8) 0.48458(5) -0.30989(3) 0.0466(2) Uani 1.00 d . . . S(2) S 0.24452(8) 0.03235(5) 0.23136(3) 0.0423(2) Uani 1.00 d . . . O(1) O 0.9007(3) 0.4543(2) -0.2854(1) 0.0882(7) Uani 1.00 d . . . O(2) O 0.6929(3) 0.6147(2) -0.3569(1) 0.0820(7) Uani 1.00 d . . . O(3) O 0.6332(4) 0.3866(3) -0.3394(1) 0.0986(9) Uani 1.00 d . . . O(4) O 0.4099(3) 0.0575(2) 0.26769(9) 0.0638(6) Uani 1.00 d . . . O(5) O 0.0581(3) 0.0375(2) 0.27415(9) 0.0626(5) Uani 1.00 d . . . O(6) O 0.2749(3) -0.0812(2) 0.20054(9) 0.0601(5) Uani 1.00 d . . . O(7) O 0.2001(2) 0.6216(1) -0.01193(9) 0.0479(4) Uani 1.00 d . . . O(8) O 0.5017(3) 0.1566(1) -0.05315(8) 0.0499(4) Uani 1.00 d . . . O(9) O 0.3688(3) 0.2568(1) -0.50466(9) 0.0544(5) Uani 1.00 d . . . N(1) N 0.1676(3) 0.1375(2) -0.18395(10) 0.0413(4) Uani 1.00 d . . . N(2) N 0.8377(3) 0.3321(2) -0.5344(1) 0.0452(5) Uani 1.00 d . . . C(1) C 0.5539(3) 0.4898(2) -0.2288(1) 0.0355(5) Uani 1.00 d . . . C(2) C 0.4599(3) 0.6079(2) -0.2208(1) 0.0403(5) Uani 1.00 d . . . C(3) C 0.3587(3) 0.6140(2) -0.1542(1) 0.0396(5) Uani 1.00 d . . . C(4) C 0.3497(3) 0.5026(2) -0.0957(1) 0.0330(5) Uani 1.00 d . . . C(5) C 0.2595(3) 0.5145(2) -0.0226(1) 0.0344(5) Uani 1.00 d . . . C(6) C 0.2486(3) 0.3939(2) 0.0383(1) 0.0320(5) Uani 1.00 d . . . C(7) C 0.1603(3) 0.4020(2) 0.1075(1) 0.0382(5) Uani 1.00 d . . . C(8) C 0.1540(3) 0.2916(2) 0.1652(1) 0.0399(5) Uani 1.00 d . . . C(9) C 0.2361(3) 0.1709(2) 0.1548(1) 0.0355(5) Uani 1.00 d . . . C(10) C 0.3208(3) 0.1610(2) 0.0863(1) 0.0343(5) Uani 1.00 d . . . C(11) C 0.3291(3) 0.2729(2) 0.02794(10) 0.0316(4) Uani 1.00 d . . . C(12) C 0.4280(3) 0.2615(2) -0.04436(10) 0.0330(5) Uani 1.00 d . . . C(13) C 0.4380(3) 0.3824(2) -0.1055(1) 0.0316(4) Uani 1.00 d . . . C(14) C 0.5398(3) 0.3759(2) -0.1721(1) 0.0347(5) Uani 1.00 d . . . C(15) C 0.0467(3) 0.2083(2) -0.1466(1) 0.0461(6) Uani 1.00 d . . . C(16) C -0.0181(3) 0.1573(2) -0.0745(1) 0.0436(5) Uani 1.00 d . . . C(17) C 0.0359(3) 0.0292(2) -0.0389(1) 0.0353(5) Uani 1.00 d . . . C(18) C 0.1593(3) -0.0426(2) -0.0800(1) 0.0464(6) Uani 1.00 d . . . C(19) C 0.2232(3) 0.0138(2) -0.1514(1) 0.0485(6) Uani 1.00 d . . . C(20) C 0.2336(4) 0.1935(3) -0.2617(1) 0.0550(7) Uani 1.00 d . . . C(21) C 0.8432(4) 0.2605(2) -0.4650(1) 0.0506(6) Uani 1.00 d . . . C(22) C 0.9066(4) 0.1309(2) -0.4501(1) 0.0472(6) Uani 1.00 d . . . C(23) C 0.9667(3) 0.0701(2) -0.5075(1) 0.0373(5) Uani 1.00 d . . . C(24) C 0.9591(3) 0.1472(2) -0.5785(1) 0.0461(6) Uani 1.00 d . . . C(25) C 0.8958(3) 0.2772(2) -0.5910(1) 0.0492(6) Uani 1.00 d . . . C(26) C 0.7682(4) 0.4717(2) -0.5497(2) 0.0628(8) Uani 1.00 d . . . C(27) C 0.4325(3) 0.1295(2) -0.5038(1) 0.0391(5) Uani 1.00 d . . . C(28) C 0.4633(3) 0.0442(2) -0.4365(1) 0.0433(5) Uani 1.00 d . . . C(29) C 0.5300(3) -0.0847(2) -0.4324(1) 0.0411(5) Uani 1.00 d . . . H(1) H 0.4645 0.6845 -0.2612 0.0462 Uiso 1.00 calc . . . H(2) H 0.2962 0.6953 -0.1483 0.0449 Uiso 1.00 calc . . . H(3) H 0.1053 0.4845 0.1142 0.0440 Uiso 1.00 calc . . . H(4) H 0.0906 0.2970 0.2123 0.0449 Uiso 1.00 calc . . . H(5) H 0.3720 0.0780 0.0788 0.0391 Uiso 1.00 calc . . . H(6) H 0.5988 0.2939 -0.1792 0.0395 Uiso 1.00 calc . . . H(7) H 0.0053 0.2959 -0.1704 0.0518 Uiso 1.00 calc . . . H(8) H -0.1013 0.2108 -0.0485 0.0498 Uiso 1.00 calc . . . H(9) H 0.1977 -0.1316 -0.0586 0.0523 Uiso 1.00 calc . . . H(10) H 0.3098 -0.0363 -0.1781 0.0541 Uiso 1.00 calc . . . H(11) H 0.7999 0.3001 -0.4252 0.0575 Uiso 1.00 calc . . . H(12) H 0.9110 0.0817 -0.3997 0.0548 Uiso 1.00 calc . . . H(13) H 0.9960 0.1094 -0.6195 0.0531 Uiso 1.00 calc . . . H(14) H 0.8950 0.3294 -0.6399 0.0571 Uiso 1.00 calc . . . H(15) H 0.4384 0.0752 -0.3922 0.0493 Uiso 1.00 calc . . . H(16) H 0.5516 -0.1429 -0.3857 0.0507 Uiso 1.00 calc . . . H(17) H 0.3728 0.1925 -0.2678 0.0663 Uiso 1.00 calc . . . H(18) H 0.1892 0.1405 -0.2914 0.0663 Uiso 1.00 calc . . . H(19) H 0.1820 0.2805 -0.2771 0.0663 Uiso 1.00 calc . . . H(20) H 0.8702 0.5257 -0.5763 0.0749 Uiso 1.00 calc . . . H(21) H 0.6578 0.4845 -0.5773 0.0749 Uiso 1.00 calc . . . H(22) H 0.7331 0.4958 -0.5041 0.0749 Uiso 1.00 calc . . . H(23) H 0.3742 0.3053 -0.5600 0.0632 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0622(4) 0.0390(3) 0.0308(3) 0.0060(2) 0.0086(2) -0.0007(2) S(2) 0.0606(4) 0.0414(3) 0.0245(3) -0.0017(2) 0.0019(2) -0.0092(2) O(1) 0.060(1) 0.116(2) 0.064(1) 0.026(1) 0.0145(9) 0.011(1) O(2) 0.109(2) 0.060(1) 0.051(1) 0.026(1) 0.022(1) 0.0194(9) O(3) 0.145(2) 0.100(2) 0.063(1) -0.041(2) 0.038(1) -0.052(1) O(4) 0.079(1) 0.069(1) 0.0440(9) 0.0009(9) -0.0233(9) -0.0096(8) O(5) 0.076(1) 0.063(1) 0.0412(9) -0.0063(9) 0.0213(8) -0.0085(8) O(6) 0.102(1) 0.0405(8) 0.0370(8) -0.0010(8) 0.0058(8) -0.0129(7) O(7) 0.0623(9) 0.0356(8) 0.0465(9) 0.0150(6) -0.0021(7) -0.0164(6) O(8) 0.079(1) 0.0302(7) 0.0357(8) 0.0090(7) 0.0117(7) -0.0076(6) O(9) 0.073(1) 0.0359(8) 0.0534(10) 0.0101(7) -0.0103(8) -0.0111(7) N(1) 0.0453(9) 0.0419(9) 0.0364(9) 0.0034(7) -0.0013(7) -0.0114(7) N(2) 0.0434(9) 0.0369(9) 0.055(1) -0.0005(7) 0.0050(8) -0.0141(8) C(1) 0.0416(10) 0.0345(9) 0.0295(9) 0.0014(7) -0.0010(7) -0.0075(7) C(2) 0.049(1) 0.0337(10) 0.035(1) 0.0026(8) -0.0041(8) -0.0026(8) C(3) 0.046(1) 0.0317(9) 0.040(1) 0.0063(7) -0.0044(8) -0.0077(8) C(4) 0.0332(9) 0.0312(9) 0.0351(10) 0.0038(7) -0.0050(7) -0.0094(7) C(5) 0.0355(9) 0.0340(9) 0.0363(10) 0.0047(7) -0.0059(7) -0.0139(8) C(6) 0.0314(9) 0.0347(9) 0.0316(9) 0.0037(7) -0.0034(7) -0.0120(7) C(7) 0.0388(10) 0.042(1) 0.036(1) 0.0067(8) -0.0016(8) -0.0178(8) C(8) 0.0397(10) 0.050(1) 0.0316(10) 0.0026(8) 0.0024(7) -0.0168(8) C(9) 0.0392(9) 0.0411(10) 0.0276(9) -0.0009(7) -0.0014(7) -0.0118(7) C(10) 0.0420(10) 0.0331(9) 0.0284(9) -0.0005(7) -0.0010(7) -0.0096(7) C(11) 0.0355(9) 0.0329(9) 0.0280(9) 0.0002(7) -0.0015(7) -0.0110(7) C(12) 0.0406(9) 0.0306(9) 0.0284(9) 0.0011(7) -0.0007(7) -0.0098(7) C(13) 0.0376(9) 0.0282(8) 0.0299(9) 0.0006(7) -0.0027(7) -0.0094(7) C(14) 0.0434(10) 0.0315(9) 0.0288(9) 0.0015(7) -0.0014(7) -0.0080(7) C(15) 0.054(1) 0.039(1) 0.044(1) 0.0113(9) -0.0033(9) -0.0107(9) C(16) 0.050(1) 0.037(1) 0.042(1) 0.0105(8) -0.0011(9) -0.0105(8) C(17) 0.0377(9) 0.0336(9) 0.037(1) 0.0044(7) -0.0051(7) -0.0134(8) C(18) 0.059(1) 0.0362(10) 0.042(1) 0.0117(9) 0.0034(9) -0.0115(9) C(19) 0.056(1) 0.043(1) 0.044(1) 0.0099(9) 0.0052(9) -0.0134(9) C(20) 0.067(2) 0.056(1) 0.037(1) 0.003(1) 0.005(1) -0.0080(10) C(21) 0.062(1) 0.047(1) 0.046(1) 0.0007(10) 0.0059(10) -0.0208(10) C(22) 0.063(1) 0.042(1) 0.037(1) 0.0003(9) 0.0060(9) -0.0145(9) C(23) 0.0364(9) 0.040(1) 0.0366(10) -0.0012(8) 0.0029(7) -0.0143(8) C(24) 0.056(1) 0.044(1) 0.037(1) 0.0024(9) 0.0029(9) -0.0131(9) C(25) 0.058(1) 0.044(1) 0.043(1) 0.0009(9) 0.0010(10) -0.0080(9) C(26) 0.065(2) 0.038(1) 0.083(2) 0.007(1) 0.000(1) -0.015(1) C(27) 0.043(1) 0.0351(9) 0.039(1) 0.0017(7) -0.0059(8) -0.0089(8) C(28) 0.052(1) 0.044(1) 0.0341(10) 0.0021(9) -0.0056(8) -0.0104(8) C(29) 0.048(1) 0.041(1) 0.0318(10) 0.0018(8) -0.0060(8) -0.0028(8) #------------------------------------------------------------------------------ # MOLCULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) O(1) 1.432(2) . . yes S(1) O(2) 1.435(2) . . yes S(1) O(3) 1.426(2) . . yes S(1) C(1) 1.781(2) . . yes S(2) O(4) 1.451(2) . . yes S(2) O(5) 1.449(2) . . yes S(2) O(6) 1.441(2) . . yes S(2) C(9) 1.779(2) . . yes O(7) C(5) 1.224(2) . . yes O(8) C(12) 1.221(2) . . yes O(9) C(27) 1.373(2) . . yes O(9) H(23) 1.039 . . no N(1) C(15) 1.339(3) . . yes N(1) C(19) 1.338(3) . . yes N(1) C(20) 1.474(3) . . yes N(2) C(21) 1.340(3) . . yes N(2) C(25) 1.345(3) . . yes N(2) C(26) 1.476(3) . . yes C(1) C(2) 1.392(3) . . yes C(1) C(14) 1.393(3) . . yes C(2) C(3) 1.385(3) . . yes C(2) H(1) 0.961 . . no C(3) C(4) 1.394(3) . . yes C(3) H(2) 0.955 . . no C(4) C(5) 1.481(3) . . yes C(4) C(13) 1.407(2) . . yes C(5) C(6) 1.483(3) . . yes C(6) C(7) 1.400(3) . . yes C(6) C(11) 1.399(2) . . yes C(7) C(8) 1.379(3) . . yes C(7) H(3) 0.953 . . no C(8) C(9) 1.400(3) . . yes C(8) H(4) 0.960 . . no C(9) C(10) 1.386(3) . . yes C(10) C(11) 1.396(3) . . yes C(10) H(5) 0.954 . . no C(11) C(12) 1.487(2) . . yes C(12) C(13) 1.487(2) . . yes C(13) C(14) 1.388(3) . . yes C(14) H(6) 0.959 . . no C(15) C(16) 1.372(3) . . yes C(15) H(7) 0.955 . . no C(16) C(17) 1.389(3) . . yes C(16) H(8) 0.957 . . no C(17) C(17) 1.488(4) . 2_555 yes C(17) C(18) 1.399(3) . . yes C(18) C(19) 1.369(3) . . yes C(18) H(9) 0.952 . . no C(19) H(10) 0.954 . . no C(20) H(17) 0.951 . . no C(20) H(18) 0.960 . . no C(20) H(19) 0.942 . . no C(21) C(22) 1.368(3) . . yes C(21) H(11) 0.955 . . no C(22) C(23) 1.399(3) . . yes C(22) H(12) 0.965 . . no C(23) C(23) 1.477(4) . 2_754 yes C(23) C(24) 1.385(3) . . yes C(24) C(25) 1.373(3) . . yes C(24) H(13) 0.956 . . no C(25) H(14) 0.947 . . no C(26) H(20) 0.951 . . no C(26) H(21) 0.945 . . no C(26) H(22) 0.956 . . no C(27) C(28) 1.387(3) . . yes C(27) C(29) 1.387(3) . 2_654 yes C(28) C(29) 1.384(3) . . yes C(28) H(15) 0.962 . . no C(29) H(16) 0.958 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(1) S(1) O(2) 111.7(1) . . . yes O(1) S(1) O(3) 114.9(2) . . . yes O(1) S(1) C(1) 104.8(1) . . . yes O(2) S(1) O(3) 113.1(2) . . . yes O(2) S(1) C(1) 105.5(1) . . . yes O(3) S(1) C(1) 105.9(1) . . . yes O(4) S(2) O(5) 113.6(1) . . . yes O(4) S(2) O(6) 113.8(1) . . . yes O(4) S(2) C(9) 102.89(10) . . . yes O(5) S(2) O(6) 114.1(1) . . . yes O(5) S(2) C(9) 105.35(10) . . . yes O(6) S(2) C(9) 105.70(9) . . . yes C(27) O(9) H(23) 105.0 . . . no C(15) N(1) C(19) 120.0(2) . . . yes C(15) N(1) C(20) 120.1(2) . . . yes C(19) N(1) C(20) 119.9(2) . . . yes C(21) N(2) C(25) 120.2(2) . . . yes C(21) N(2) C(26) 120.5(2) . . . yes C(25) N(2) C(26) 119.3(2) . . . yes S(1) C(1) C(2) 120.1(1) . . . yes S(1) C(1) C(14) 118.6(1) . . . yes C(2) C(1) C(14) 121.1(2) . . . yes C(1) C(2) C(3) 119.5(2) . . . yes C(1) C(2) H(1) 120.3 . . . no C(3) C(2) H(1) 120.2 . . . no C(2) C(3) C(4) 120.3(2) . . . yes C(2) C(3) H(2) 119.7 . . . no C(4) C(3) H(2) 120.0 . . . no C(3) C(4) C(5) 119.5(2) . . . yes C(3) C(4) C(13) 119.6(2) . . . yes C(5) C(4) C(13) 120.8(2) . . . yes O(7) C(5) C(4) 121.1(2) . . . yes O(7) C(5) C(6) 120.6(2) . . . yes C(4) C(5) C(6) 118.3(2) . . . yes C(5) C(6) C(7) 119.5(2) . . . yes C(5) C(6) C(11) 120.9(2) . . . yes C(7) C(6) C(11) 119.6(2) . . . yes C(6) C(7) C(8) 120.2(2) . . . yes C(6) C(7) H(3) 119.3 . . . no C(8) C(7) H(3) 120.5 . . . no C(7) C(8) C(9) 120.1(2) . . . yes C(7) C(8) H(4) 120.0 . . . no C(9) C(8) H(4) 119.9 . . . no S(2) C(9) C(8) 119.6(1) . . . yes S(2) C(9) C(10) 119.9(1) . . . yes C(8) C(9) C(10) 120.3(2) . . . yes C(9) C(10) C(11) 119.7(2) . . . yes C(9) C(10) H(5) 120.2 . . . no C(11) C(10) H(5) 120.1 . . . no C(6) C(11) C(10) 120.1(2) . . . yes C(6) C(11) C(12) 121.0(2) . . . yes C(10) C(11) C(12) 118.9(2) . . . yes O(8) C(12) C(11) 121.1(2) . . . yes O(8) C(12) C(13) 120.8(2) . . . yes C(11) C(12) C(13) 118.1(2) . . . yes C(4) C(13) C(12) 120.7(2) . . . yes C(4) C(13) C(14) 120.2(2) . . . yes C(12) C(13) C(14) 119.1(2) . . . yes C(1) C(14) C(13) 119.2(2) . . . yes C(1) C(14) H(6) 120.5 . . . no C(13) C(14) H(6) 120.3 . . . no N(1) C(15) C(16) 121.0(2) . . . yes N(1) C(15) H(7) 119.7 . . . no C(16) C(15) H(7) 119.4 . . . no C(15) C(16) C(17) 120.7(2) . . . yes C(15) C(16) H(8) 119.4 . . . no C(17) C(16) H(8) 119.8 . . . no C(16) C(17) C(17) 121.7(2) . . 2_555 yes C(16) C(17) C(18) 116.7(2) . . . yes C(17) C(17) C(18) 121.6(2) 2_555 . . yes C(17) C(18) C(19) 120.3(2) . . . yes C(17) C(18) H(9) 120.0 . . . no C(19) C(18) H(9) 119.7 . . . no N(1) C(19) C(18) 121.3(2) . . . yes N(1) C(19) H(10) 119.8 . . . no C(18) C(19) H(10) 118.9 . . . no N(1) C(20) H(17) 109.7 . . . no N(1) C(20) H(18) 109.1 . . . no N(1) C(20) H(19) 110.3 . . . no H(17) C(20) H(18) 108.5 . . . no H(17) C(20) H(19) 110.0 . . . no H(18) C(20) H(19) 109.3 . . . no N(2) C(21) C(22) 121.1(2) . . . yes N(2) C(21) H(11) 119.5 . . . no C(22) C(21) H(11) 119.4 . . . no C(21) C(22) C(23) 120.4(2) . . . yes C(21) C(22) H(12) 119.6 . . . no C(23) C(22) H(12) 120.0 . . . no C(22) C(23) C(23) 121.1(2) . . 2_754 yes C(22) C(23) C(24) 116.9(2) . . . yes C(23) C(23) C(24) 122.0(2) 2_754 . . yes C(23) C(24) C(25) 120.9(2) . . . yes C(23) C(24) H(13) 119.8 . . . no C(25) C(24) H(13) 119.3 . . . no N(2) C(25) C(24) 120.6(2) . . . yes N(2) C(25) H(14) 119.5 . . . no C(24) C(25) H(14) 119.9 . . . no N(2) C(26) H(20) 109.6 . . . no N(2) C(26) H(21) 110.2 . . . no N(2) C(26) H(22) 109.1 . . . no H(20) C(26) H(21) 109.7 . . . no H(20) C(26) H(22) 108.8 . . . no H(21) C(26) H(22) 109.4 . . . no O(9) C(27) C(28) 118.2(2) . . . yes O(9) C(27) C(29) 122.5(2) . . 2_654 yes C(28) C(27) C(29) 119.4(2) . . 2_654 yes C(27) C(28) C(29) 120.7(2) . . . yes C(27) C(28) H(15) 119.6 . . . no C(29) C(28) H(15) 119.8 . . . no C(27) C(29) C(28) 120.0(2) 2_654 . . yes C(27) C(29) H(16) 119.9 2_654 . . no C(28) C(29) H(16) 120.2 . . . no 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 S(1) C(1) C(2) C(3) -172.6(2) . . . . yes S(1) C(1) C(14) C(13) 172.7(1) . . . . yes S(2) C(9) C(8) C(7) 175.0(1) . . . . yes S(2) C(9) C(10) C(11) -174.4(1) . . . . yes O(1) S(1) C(1) C(2) 114.1(2) . . . . yes O(1) S(1) C(1) C(14) -61.7(2) . . . . yes O(2) S(1) C(1) C(2) -3.8(2) . . . . yes O(2) S(1) C(1) C(14) -179.7(2) . . . . yes O(3) S(1) C(1) C(2) -124.0(2) . . . . yes O(3) S(1) C(1) C(14) 60.1(2) . . . . yes O(4) S(2) C(9) C(8) -78.5(2) . . . . yes O(4) S(2) C(9) C(10) 97.7(2) . . . . yes O(5) S(2) C(9) C(8) 40.8(2) . . . . yes O(5) S(2) C(9) C(10) -143.0(2) . . . . yes O(6) S(2) C(9) C(8) 161.8(2) . . . . yes O(6) S(2) C(9) C(10) -22.0(2) . . . . yes O(7) C(5) C(4) C(3) -3.1(3) . . . . yes O(7) C(5) C(4) C(13) 172.6(2) . . . . yes O(7) C(5) C(6) C(7) 3.3(3) . . . . yes O(7) C(5) C(6) C(11) -175.3(2) . . . . yes O(8) C(12) C(11) C(6) 178.6(2) . . . . yes O(8) C(12) C(11) C(10) -0.2(3) . . . . yes O(8) C(12) C(13) C(4) 178.7(2) . . . . yes O(8) C(12) C(13) C(14) -2.7(3) . . . . yes O(9) C(27) C(28) C(29) -179.1(2) . . . . yes O(9) C(27) C(29) C(28) 179.1(2) . . 2_654 2_654 yes N(1) C(15) C(16) C(17) -1.9(3) . . . . yes N(1) C(19) C(18) C(17) -1.0(4) . . . . yes N(2) C(21) C(22) C(23) -0.2(4) . . . . yes N(2) C(25) C(24) C(23) -0.7(4) . . . . yes C(1) C(2) C(3) C(4) -0.4(3) . . . . yes C(1) C(14) C(13) C(4) 0.3(3) . . . . yes C(1) C(14) C(13) C(12) -178.3(2) . . . . yes C(2) C(1) C(14) C(13) -3.1(3) . . . . yes C(2) C(3) C(4) C(5) 173.4(2) . . . . yes C(2) C(3) C(4) C(13) -2.3(3) . . . . yes C(3) C(2) C(1) C(14) 3.2(3) . . . . yes C(3) C(4) C(5) C(6) 178.9(2) . . . . yes C(3) C(4) C(13) C(12) -179.1(2) . . . . yes C(3) C(4) C(13) C(14) 2.4(3) . . . . yes C(4) C(5) C(6) C(7) -178.6(2) . . . . yes C(4) C(5) C(6) C(11) 2.7(2) . . . . yes C(4) C(13) C(12) C(11) -2.4(3) . . . . yes C(5) C(4) C(13) C(12) 5.3(3) . . . . yes C(5) C(4) C(13) C(14) -173.3(2) . . . . yes C(5) C(6) C(7) C(8) -178.1(2) . . . . yes C(5) C(6) C(11) C(10) 178.7(2) . . . . yes C(5) C(6) C(11) C(12) 0.0(3) . . . . yes C(6) C(5) C(4) C(13) -5.5(3) . . . . yes C(6) C(7) C(8) C(9) 0.0(3) . . . . yes C(6) C(11) C(10) C(9) -1.3(3) . . . . yes C(6) C(11) C(12) C(13) -0.3(3) . . . . yes C(7) C(6) C(11) C(10) 0.1(3) . . . . yes C(7) C(6) C(11) C(12) -178.6(2) . . . . yes C(7) C(8) C(9) C(10) -1.2(3) . . . . yes C(8) C(7) C(6) C(11) 0.5(3) . . . . yes C(8) C(9) C(10) C(11) 1.8(3) . . . . yes C(9) C(10) C(11) C(12) 177.4(2) . . . . yes C(10) C(11) C(12) C(13) -179.0(2) . . . . yes C(11) C(12) C(13) C(14) 176.2(2) . . . . yes C(15) N(1) C(19) C(18) -0.2(4) . . . . yes C(15) C(16) C(17) C(17) -178.7(2) . . . 2_555 yes C(15) C(16) C(17) C(18) 0.6(3) . . . . yes C(16) C(15) N(1) C(19) 1.7(3) . . . . yes C(16) C(15) N(1) C(20) 179.2(2) . . . . yes C(16) C(17) C(17) C(16) 180.0 . . 2_555 2_555 yes C(16) C(17) C(17) C(18) -0.7(4) . . 2_555 2_555 yes C(16) C(17) C(18) C(19) 0.8(3) . . . . yes C(17) C(17) C(18) C(19) 179.9(2) . 2_555 2_555 2_555 yes C(18) C(17) C(17) C(18) 180.0 . . 2_555 2_555 yes C(18) C(19) N(1) C(20) -177.8(2) . . . . yes C(21) N(2) C(25) C(24) 0.7(3) . . . . yes C(21) C(22) C(23) C(23) -179.2(2) . . . 2_754 yes C(21) C(22) C(23) C(24) 0.3(3) . . . . yes C(22) C(21) N(2) C(25) -0.2(4) . . . . yes C(22) C(21) N(2) C(26) 179.7(2) . . . . yes C(22) C(23) C(23) C(22) 180.0 . . 2_754 2_754 yes C(22) C(23) C(23) C(24) -0.5(4) . . 2_754 2_754 yes C(22) C(23) C(24) C(25) 0.2(3) . . . . yes C(23) C(23) C(24) C(25) -179.7(2) . 2_754 2_754 2_754 yes C(24) C(23) C(23) C(24) -180.0 . . 2_754 2_754 yes C(24) C(25) N(2) C(26) -179.3(2) . . . . yes C(24) C(25) N(2) C(26) -179.3(2) . . . . yes #-------------------------------------------------------------------- data_c1 database_code_CSD 191675 # CHEMICAL DATA _chemical_formula_sum 'C38 H36 N2 O14 S2 ' _chemical_formula_moiety 'C14 H6 O8 S2, C12 H14 N2, 2(C6 H6 O2), 2(H2 O)' _chemical_formula_weight 808.83 _chemical_melting_point ? 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 C C 0.0033 0.0016 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 H H 0.0000 0.0000 International Tables Vol C Tables 4.2.6.8 and 6.1.1.4 #------------------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 7.129(4) _cell_length_b 8.636(5) _cell_length_c 15.185(8) _cell_angle_alpha 96.15(2) _cell_angle_beta 102.40(2) _cell_angle_gamma 98.27(1) _cell_volume 894.3(9) _cell_formula_units_Z 1 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.3 _cell_measurement_theta_max 14.9 _cell_measurement_temperature 296.2 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 _exptl_absorpt_coefficient_mu 2.010 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_T_max 0.900 #------------------------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w _diffrn_reflns_number 3471 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_theta_max 69.86 _diffrn_measured_fraction_theta_max 0.9882 _diffrn_reflns_theta_full 69.86 _diffrn_measured_fraction_theta_full 0.9882 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.037 _computing_data_collection . _computing_cell_refinement . _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------- # REFINEMENT DATA _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. The hydrogen atoms attached to oxygen of hydroqinone were omitted. The hydrogen atoms H15 and H16 were found in D-fourier map and refined riding on their carrier oxygen atoms by using 0.96 for OH distance and 1.5 for H---H distance to a tolerance of plus or minus 0.04. ; _reflns_number_total 3341 _reflns_number_gt 2810 _reflns_threshold_expression F^2^>2.0\s(F^2^) _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 3341 _refine_ls_number_parameters 259 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 1.345 _refine_ls_restrained_S_all 1.344 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.428 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.066 #------------------------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.37996(8) 0.12100(7) 0.25444(4) 0.0455(2) Uani 1 1 d . . . O1 O 0.3773(4) 0.2499(2) 0.32280(14) 0.0724(6) Uani 1 1 d . . . O2 O 0.5508(3) 0.0483(3) 0.27678(14) 0.0645(5) Uani 1 1 d . . . O3 O 0.2020(3) 0.0059(2) 0.22985(14) 0.0645(5) Uani 1 1 d . . . O4 O 0.3821(3) 0.3165(2) -0.16328(12) 0.0592(5) Uani 1 1 d . . . O5 O -0.0365(3) 0.4547(2) 0.17369(13) 0.0618(5) Uani 1 1 d . . . O6 O 0.8627(3) 0.1467(3) 0.19130(16) 0.0678(6) Uani 1 1 d D . . O7 O 0.7045(3) 0.6681(3) 0.51592(14) 0.0703(6) Uani 1 1 d . . . N1 N 1.2281(3) 0.7596(2) 0.37137(13) 0.0445(5) Uani 1 1 d . . . C1 C 0.3954(3) 0.2057(3) 0.15407(15) 0.0406(5) Uani 1 1 d . . . C2 C 0.4686(3) 0.3648(3) 0.15982(15) 0.0415(5) Uani 1 1 d . . . C3 C 0.4831(3) 0.4293(2) 0.08119(14) 0.0376(5) Uani 1 1 d . . . C4 C 0.4250(3) 0.3333(2) -0.00349(15) 0.0392(5) Uani 1 1 d . . . C5 C 0.3536(4) 0.1732(3) -0.00800(16) 0.0477(5) Uani 1 1 d . . . C6 C 0.3386(4) 0.1100(3) 0.06985(18) 0.0491(5) Uani 1 1 d . . . C7 C 0.4375(3) 0.3997(3) -0.08903(15) 0.0412(5) Uani 1 1 d . . . C8 C 1.3130(4) 0.8172(3) 0.4573(2) 0.0621(7) Uani 1 1 d . . . C9 C 1.2277(4) 0.9113(4) 0.50957(18) 0.0632(7) Uani 1 1 d . . . C10 C 1.0472(3) 0.9489(2) 0.47216(15) 0.0418(5) Uani 1 1 d . . . C11 C 0.9586(4) 0.8833(3) 0.38306(16) 0.0488(5) Uani 1 1 d . . . C12 C 1.0511(4) 0.7887(3) 0.33413(17) 0.0505(6) Uani 1 1 d . . . C13 C 1.3321(4) 0.6650(3) 0.3171(2) 0.0606(7) Uani 1 1 d . . . C14 C 0.8517(4) 0.5825(3) 0.51040(16) 0.0465(5) Uani 1 1 d . . . C15 C 1.0055(4) 0.5868(3) 0.58224(17) 0.0526(6) Uani 1 1 d . . . C16 C 0.8469(4) 0.4963(4) 0.42769(18) 0.0581(7) Uani 1 1 d . . . C17 C -0.0184(3) 0.4749(3) 0.08697(17) 0.0484(5) Uani 1 1 d . . . C18 C 0.0498(4) 0.6242(3) 0.07012(18) 0.0534(6) Uani 1 1 d . . . C19 C 0.0676(4) 0.6489(3) -0.01649(18) 0.0506(6) Uani 1 1 d . . . H1 H 0.5096 0.4307 0.2182 0.048 Uiso 1 1 calc . . . H2 H 0.3160 0.1064 -0.0653 0.056 Uiso 1 1 calc . . . H3 H 0.2885 -0.0001 0.0660 0.058 Uiso 1 1 calc . . . H4 H 1.4399 0.7948 0.4828 0.073 Uiso 1 1 calc . . . H5 H 1.2907 0.9505 0.5719 0.072 Uiso 1 1 calc . . . H6 H 0.8334 0.9062 0.3555 0.057 Uiso 1 1 calc . . . H7 H 0.9861 0.7405 0.2728 0.060 Uiso 1 1 calc . . . H8 H 1.4513 0.7250 0.3131 0.071 Uiso 1 1 calc . . . H9 H 1.3589 0.5729 0.3446 0.071 Uiso 1 1 calc . . . H10 H 1.2525 0.6299 0.2568 0.071 Uiso 1 1 calc . . . H11 H 1.0103 0.6479 0.6399 0.061 Uiso 1 1 calc . . . H12 H 0.7399 0.4942 0.3767 0.067 Uiso 1 1 calc . . . H13 H 0.0820 0.7106 0.1186 0.064 Uiso 1 1 calc . . . H14 H 0.1151 0.7538 -0.0282 0.060 Uiso 1 1 calc . . . H15 H 0.770(3) 0.117(4) 0.2263(19) 0.085 Uiso 1 1 d D . . H16 H 0.971(3) 0.095(4) 0.210(2) 0.085 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 0.0429(4) 0.0521(4) 0.0473(3) 0.0140(2) 0.0169(2) 0.0130(2) O1 0.1058(17) 0.0653(12) 0.0582(12) 0.0070(9) 0.0435(12) 0.0189(11) O2 0.0535(11) 0.0918(14) 0.0610(11) 0.0338(10) 0.0169(9) 0.0314(10) O3 0.0510(11) 0.0688(12) 0.0759(13) 0.0268(10) 0.0180(9) 0.0008(9) O4 0.0858(14) 0.0462(9) 0.0413(9) -0.0033(7) 0.0158(9) 0.0030(9) O5 0.0673(12) 0.0700(12) 0.0471(10) 0.0054(8) 0.0150(8) 0.0079(9) O6 0.0528(12) 0.0755(13) 0.0842(14) 0.0249(11) 0.0250(10) 0.0172(10) O7 0.0699(13) 0.0937(15) 0.0605(11) 0.0144(10) 0.0184(10) 0.0499(12) N1 0.0470(11) 0.0441(10) 0.0455(11) 0.0086(8) 0.0134(8) 0.0120(8) C1 0.0333(11) 0.0459(11) 0.0458(12) 0.0090(9) 0.0114(9) 0.0114(8) C2 0.0396(12) 0.0450(11) 0.0417(11) 0.0044(9) 0.0117(9) 0.0115(9) C3 0.0348(11) 0.0395(11) 0.0399(11) 0.0031(8) 0.0103(8) 0.0108(8) C4 0.0384(11) 0.0402(10) 0.0396(11) 0.0029(9) 0.0104(8) 0.0089(8) C5 0.0543(14) 0.0406(11) 0.0449(12) -0.0008(9) 0.0096(10) 0.0055(10) C6 0.0533(14) 0.0412(11) 0.0507(13) 0.0055(10) 0.0099(11) 0.0052(10) C7 0.0449(12) 0.0410(11) 0.0371(10) -0.0012(8) 0.0099(9) 0.0098(9) C8 0.0541(16) 0.0728(17) 0.0583(15) 0.0027(13) 0.0000(12) 0.0319(13) C9 0.0607(17) 0.0807(18) 0.0463(14) -0.0039(13) -0.0011(12) 0.0362(14) C10 0.0433(12) 0.0435(11) 0.0426(11) 0.0133(9) 0.0121(9) 0.0121(9) C11 0.0425(13) 0.0636(14) 0.0416(12) 0.0098(10) 0.0090(9) 0.0130(10) C12 0.0458(13) 0.0611(14) 0.0455(13) 0.0068(11) 0.0119(10) 0.0110(11) C13 0.0587(16) 0.0648(16) 0.0610(16) -0.0032(13) 0.0185(13) 0.0213(13) C14 0.0477(13) 0.0493(12) 0.0480(13) 0.0106(10) 0.0157(10) 0.0165(10) C15 0.0613(16) 0.0555(13) 0.0428(12) 0.0011(10) 0.0139(11) 0.0172(12) C16 0.0547(15) 0.0742(17) 0.0439(13) 0.0025(12) 0.0031(11) 0.0232(13) C17 0.0392(12) 0.0570(13) 0.0485(13) 0.0049(10) 0.0097(10) 0.0095(10) C18 0.0524(14) 0.0532(13) 0.0505(13) -0.0011(10) 0.0085(11) 0.0070(11) C19 0.0466(13) 0.0500(12) 0.0530(13) 0.0024(10) 0.0104(11) 0.0066(10) #------------------------------------------------------------------------------- # MOLCULAR GEOMETRY _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 O2 1.442(2) . ? S1 O1 1.444(2) . ? S1 O3 1.446(2) . ? S1 C1 1.777(2) . ? O4 C7 1.223(3) . ? O5 C17 1.377(3) . ? O6 H15 0.96(3) . ? O6 H16 0.95(3) . ? O7 C14 1.379(3) . ? N1 C8 1.324(3) . ? N1 C12 1.338(3) . ? N1 C13 1.479(3) . ? C1 C2 1.385(3) . ? C1 C6 1.392(3) . ? C2 C3 1.388(3) . ? C2 H1 0.963 . ? C3 C4 1.399(3) . ? C3 C7 1.486(3) 2_665 ? C4 C5 1.392(3) . ? C4 C7 1.490(3) . ? C5 C6 1.372(4) . ? C5 H2 0.953 . ? C6 H3 0.957 . ? C7 C3 1.486(3) 2_665 ? C8 C9 1.367(4) . ? C8 H4 0.960 . ? C9 C10 1.389(4) . ? C9 H5 0.958 . ? C10 C11 1.384(3) . ? C10 C10 1.484(4) 2_776 ? C11 C12 1.375(4) . ? C11 H6 0.958 . ? C12 H7 0.965 . ? C13 H8 0.947 . ? C13 H9 0.961 . ? C13 H10 0.959 . ? C14 C15 1.364(4) . ? C14 C16 1.381(4) . ? C15 C16 1.381(4) 2_766 ? C15 H11 0.964 . ? C16 C15 1.381(4) 2_766 ? C16 H12 0.960 . ? C17 C19 1.377(3) 2_565 ? C17 C18 1.381(4) . ? C18 C19 1.384(4) . ? C18 H13 0.955 . ? C19 C17 1.377(3) 2_565 ? C19 H14 0.969 . ? 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 O2 S1 O1 112.82(14) . . ? O2 S1 O3 112.17(13) . . ? O1 S1 O3 113.51(14) . . ? O2 S1 C1 105.83(10) . . ? O1 S1 C1 106.20(12) . . ? O3 S1 C1 105.53(11) . . ? H15 O6 H16 107(2) . . ? C8 N1 C12 120.0(2) . . ? C8 N1 C13 119.3(2) . . ? C12 N1 C13 120.7(2) . . ? C2 C1 C6 120.2(2) . . ? C2 C1 S1 120.24(18) . . ? C6 C1 S1 119.52(17) . . ? C1 C2 C3 119.8(2) . . ? C1 C2 H1 120 . . ? C3 C2 H1 120.0 . . ? C2 C3 C4 119.9(2) . . ? C2 C3 C7 118.9(2) . 2_665 ? C4 C3 C7 121.17(19) . 2_665 ? C5 C4 C3 119.5(2) . . ? C5 C4 C7 119.4(2) . . ? C3 C4 C7 121.05(19) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H2 119.5 . . ? C4 C5 H2 120.1 . . ? C5 C6 C1 120.1(2) . . ? C5 C6 H3 119.8 . . ? C1 C6 H3 120.1 . . ? O4 C7 C3 121.2(2) . 2_665 ? O4 C7 C4 121.1(2) . . ? C3 C7 C4 117.77(19) 2_665 . ? N1 C8 C9 121.9(2) . . ? N1 C8 H4 118.7 . . ? C9 C8 H4 119.4 . . ? C8 C9 C10 119.7(2) . . ? C8 C9 H5 120.5 . . ? C10 C9 H5 119.8 . . ? C11 C10 C9 117.4(2) . . ? C11 C10 C10 122.2(3) . 2_776 ? C9 C10 C10 120.4(3) . 2_776 ? C12 C11 C10 120.2(2) . . ? C12 C11 H6 120.4 . . ? C10 C11 H6 119.4 . . ? N1 C12 C11 120.7(2) . . ? N1 C12 H7 119.7 . . ? C11 C12 H7 119.6 . . ? N1 C13 H8 111.0 . . ? N1 C13 H9 110.1 . . ? H8 C13 H9 108.9 . . ? N1 C13 H10 110.0 . . ? H8 C13 H10 109.0 . . ? H9 C13 H10 107.8 . . ? C15 C14 O7 122.2(2) . . ? C15 C14 C16 119.3(2) . . ? O7 C14 C16 118.4(2) . . ? C14 C15 C16 120.1(2) . 2_766 ? C14 C15 H11 119.6 . . ? C16 C15 H11 120.3 2_766 . ? C15 C16 C14 120.6(2) 2_766 . ? C15 C16 H12 119.8 2_766 . ? C14 C16 H12 119.6 . . ? C19 C17 O5 122.0(2) 2_565 . ? C19 C17 C18 119.1(2) 2_565 . ? O5 C17 C18 118.9(2) . . ? C17 C18 C19 120.4(2) . . ? C17 C18 H13 119.3 . . ? C19 C18 H13 120.4 . . ? C17 C19 C18 120.6(2) 2_565 . ? C17 C19 H14 119.2 2_565 . ? C18 C19 H14 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 C1 C2 -97.7(2) . . . . ? O1 S1 C1 C2 22.5(2) . . . . ? O3 S1 C1 C2 143.27(19) . . . . ? O2 S1 C1 C6 80.5(2) . . . . ? O1 S1 C1 C6 -159.4(2) . . . . ? O3 S1 C1 C6 -38.6(2) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? S1 C1 C2 C3 178.93(16) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C7 -179.88(19) . . . 2_665 ? C2 C3 C4 C5 -0.2(3) . . . . ? C7 C3 C4 C5 179.2(2) 2_665 . . . ? C2 C3 C4 C7 179.5(2) . . . . ? C7 C3 C4 C7 -1.1(4) 2_665 . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C7 C4 C5 C6 -179.2(2) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? S1 C1 C6 C5 -178.64(19) . . . . ? C5 C4 C7 O4 1.6(4) . . . . ? C3 C4 C7 O4 -178.1(2) . . . . ? C5 C4 C7 C3 -179.2(2) . . . 2_665 ? C3 C4 C7 C3 1.0(3) . . . 2_665 ? C12 N1 C8 C9 -2.2(5) . . . . ? C13 N1 C8 C9 177.1(3) . . . . ? N1 C8 C9 C10 -0.2(5) . . . . ? C8 C9 C10 C11 2.2(4) . . . . ? C8 C9 C10 C10 -179.8(3) . . . 2_776 ? C9 C10 C11 C12 -1.7(4) . . . . ? C10 C10 C11 C12 -179.7(3) 2_776 . . . ? C8 N1 C12 C11 2.6(4) . . . . ? C13 N1 C12 C11 -176.6(2) . . . . ? C10 C11 C12 N1 -0.6(4) . . . . ? O7 C14 C15 C16 -177.5(2) . . . 2_766 ? C16 C14 C15 C16 -0.9(5) . . . 2_766 ? C15 C14 C16 C15 0.9(5) . . . 2_766 ? O7 C14 C16 C15 177.6(2) . . . 2_766 ? C19 C17 C18 C19 0.2(4) 2_565 . . . ? O5 C17 C18 C19 -179.3(2) . . . . ? C17 C18 C19 C17 -0.2(4) . . . 2_565 ?