# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Peter J. Skabara' 'Simon J. Coles' 'Pierre Frere' 'Michael B. Hursthouse' 'Tahir Khan' 'Joseph J.W. McDouall' 'E. McInnes' _publ_contact_author_name 'Dr Peter J Skabara' _publ_contact_author_address ; Chemistry University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email PETER.SKABARA@MAN.AC.UK _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; A combined substituent and supramolecular approach for improving the electron donor properties of 1,3-dithiole-2-thione derivatives ; data_compound_11h _database_code_CSD 213283 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 O6 S3' _chemical_formula_weight 462.53 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.457(2) _cell_length_b 18.553(4) _cell_length_c 13.006(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2040.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 27698 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.275 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.761 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27698 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2321 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _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^)+(0.1000P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2321 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1679 _refine_ls_goodness_of_fit_ref 1.423 _refine_ls_restrained_S_all 1.423 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.004 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 0.0000 0.31110(5) 0.7500 0.0625(4) Uani 1 2 d S . . S2 S 0.10941(7) 0.17587(3) 0.66479(4) 0.0355(2) Uani 1 1 d . . . O1 O 0.26726(18) 0.04248(10) 0.62710(12) 0.0398(4) Uani 1 1 d . . . O2 O -0.20588(18) 0.01004(8) 0.62874(10) 0.0321(4) Uani 1 1 d . . . O3 O -0.1436(2) -0.23969(9) 0.57888(14) 0.0512(5) Uani 1 1 d . . . C1 C 0.0000 0.22778(17) 0.7500 0.0374(7) Uani 1 2 d S . . C2 C 0.0496(2) 0.09137(10) 0.70908(14) 0.0269(4) Uani 1 1 d . . . C3 C 0.1300(2) 0.03057(12) 0.65343(13) 0.0296(5) Uani 1 1 d . . . C4 C 0.0523(2) -0.03813(11) 0.63180(13) 0.0283(4) Uani 1 1 d . . . C5 C -0.1117(2) -0.04883(11) 0.62104(13) 0.0275(5) Uani 1 1 d . . . C6 C -0.3721(3) -0.00089(13) 0.62671(18) 0.0398(5) Uani 1 1 d . . . H6A H -0.4026 -0.0192 0.5606 0.060 Uiso 1 1 calc R . . H6B H -0.4249 0.0441 0.6391 0.060 Uiso 1 1 calc R . . H6C H -0.4011 -0.0349 0.6790 0.060 Uiso 1 1 calc R . . C7 C -0.1718(3) -0.11684(12) 0.60240(14) 0.0331(5) Uani 1 1 d . . . H7 H -0.2802 -0.1234 0.5948 0.040 Uiso 1 1 calc R . . C8 C -0.0697(3) -0.17576(11) 0.59497(17) 0.0374(5) Uani 1 1 d . . . C9 C -0.0457(5) -0.30211(15) 0.5672(3) 0.0761(11) Uani 1 1 d . . . H9A H 0.0233 -0.2956 0.5093 0.114 Uiso 1 1 calc R . . H9B H -0.1110 -0.3437 0.5562 0.114 Uiso 1 1 calc R . . H9C H 0.0164 -0.3088 0.6283 0.114 Uiso 1 1 calc R . . C10 C 0.0932(3) -0.16668(13) 0.60326(19) 0.0429(6) Uani 1 1 d . . . H10 H 0.1613 -0.2058 0.5973 0.051 Uiso 1 1 calc R . . C11 C 0.1511(3) -0.09844(12) 0.62047(15) 0.0363(5) Uani 1 1 d . . . H11 H 0.2600 -0.0920 0.6248 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0653(7) 0.0494(6) 0.0729(7) 0.000 -0.0038(5) 0.000 S2 0.0345(4) 0.0364(4) 0.0355(4) 0.0039(2) 0.0059(2) -0.0030(2) O1 0.0237(8) 0.0548(10) 0.0409(8) -0.0031(7) 0.0098(6) -0.0002(7) O2 0.0232(8) 0.0323(8) 0.0407(8) -0.0046(6) -0.0030(5) 0.0053(5) O3 0.0694(13) 0.0309(9) 0.0535(10) -0.0042(7) -0.0116(9) 0.0038(7) C1 0.0315(16) 0.0432(17) 0.0374(15) 0.000 -0.0035(12) 0.000 C2 0.0209(9) 0.0342(10) 0.0257(8) -0.0005(8) 0.0011(7) 0.0002(7) C3 0.0248(10) 0.0410(11) 0.0230(8) 0.0026(8) 0.0003(7) 0.0029(8) C4 0.0261(10) 0.0374(10) 0.0213(8) -0.0008(7) 0.0012(7) 0.0057(8) C5 0.0261(10) 0.0349(10) 0.0215(8) -0.0005(7) 0.0012(7) 0.0067(8) C6 0.0244(12) 0.0461(13) 0.0488(13) -0.0034(10) -0.0017(8) 0.0039(9) C7 0.0328(11) 0.0374(11) 0.0290(9) -0.0022(8) -0.0042(8) 0.0024(9) C8 0.0518(15) 0.0310(11) 0.0293(10) -0.0018(8) -0.0053(9) 0.0052(9) C9 0.101(3) 0.0344(13) 0.093(2) -0.0072(15) -0.036(2) 0.0184(15) C10 0.0488(15) 0.0397(12) 0.0401(12) -0.0042(9) -0.0054(10) 0.0187(10) C11 0.0312(12) 0.0447(13) 0.0330(10) -0.0036(9) -0.0007(8) 0.0131(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.546(3) . ? S2 C1 1.7354(19) . ? S2 C2 1.7452(19) . ? O1 C3 1.230(3) . ? O2 C5 1.356(2) . ? O2 C6 1.420(3) . ? O3 C8 1.357(3) . ? O3 C9 1.432(3) . ? C1 S2 1.7354(19) 3_556 ? C2 C2 1.355(4) 3_556 ? C2 C3 1.503(3) . ? C3 C4 1.462(3) . ? C4 C11 1.405(3) . ? C4 C5 1.407(3) . ? C5 C7 1.382(3) . ? C7 C8 1.396(3) . ? C8 C10 1.392(4) . ? C10 C11 1.376(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S2 C2 97.65(11) . . ? C5 O2 C6 117.72(17) . . ? C8 O3 C9 117.2(2) . . ? S1 C1 S2 123.70(9) . 3_556 ? S1 C1 S2 123.70(9) . . ? S2 C1 S2 112.60(18) 3_556 . ? C2 C2 C3 131.18(11) 3_556 . ? C2 C2 S2 116.02(6) 3_556 . ? C3 C2 S2 112.58(14) . . ? O1 C3 C4 121.85(19) . . ? O1 C3 C2 115.24(19) . . ? C4 C3 C2 122.91(18) . . ? C11 C4 C5 117.62(19) . . ? C11 C4 C3 116.5(2) . . ? C5 C4 C3 125.83(18) . . ? O2 C5 C7 122.18(19) . . ? O2 C5 C4 117.25(18) . . ? C7 C5 C4 120.57(18) . . ? C5 C7 C8 120.0(2) . . ? O3 C8 C10 125.0(2) . . ? O3 C8 C7 114.2(2) . . ? C10 C8 C7 120.8(2) . . ? C11 C10 C8 118.5(2) . . ? C10 C11 C4 122.6(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.599 _refine_diff_density_min -0.879 _refine_diff_density_rms 0.083 #===END data_compound_8d _database_code_CSD 213284 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 O6 S2' _chemical_formula_weight 430.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.913(2) _cell_length_b 10.263(2) _cell_length_c 10.766(2) _cell_angle_alpha 94.82(3) _cell_angle_beta 111.22(3) _cell_angle_gamma 107.38(3) _cell_volume 951.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10790 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10790 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4254 _reflns_number_gt 2988 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _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^)+(0.1000P)^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 4254 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.10254(6) 0.42267(6) 0.29678(5) 0.03087(17) Uani 1 1 d . . . S2 S -0.02634(7) 0.11137(6) 0.19843(5) 0.03283(18) Uani 1 1 d . . . O1 O -0.27617(18) 0.86947(16) 0.47675(15) 0.0361(4) Uani 1 1 d . . . O2 O 0.02563(18) 0.64061(16) 0.36138(16) 0.0378(4) Uani 1 1 d . . . O3 O -0.81475(19) -0.35234(16) 0.06170(15) 0.0365(4) Uani 1 1 d . . . O4 O -0.28444(19) -0.11295(16) 0.13034(16) 0.0367(4) Uani 1 1 d . . . O5 O -0.32971(17) 0.25851(14) 0.25642(13) 0.0270(3) Uani 1 1 d . . . O6 O 0.25514(19) 0.27294(18) 0.24181(15) 0.0403(4) Uani 1 1 d . . . C2 C 0.1335(3) 0.2700(2) 0.2457(2) 0.0325(5) Uani 1 1 d . . . C3 C -0.0875(3) 0.3376(2) 0.27497(19) 0.0278(5) Uani 1 1 d . . . C4 C -0.1490(3) 0.1889(2) 0.22855(19) 0.0269(5) Uani 1 1 d . . . C5 C -0.2008(2) 0.3776(2) 0.29177(19) 0.0252(4) Uani 1 1 d . . . C6 C -0.2235(2) 0.5053(2) 0.33555(19) 0.0257(4) Uani 1 1 d . . . C7 C -0.3627(3) 0.4991(2) 0.3415(2) 0.0299(5) Uani 1 1 d . . . H7 H -0.4423 0.4128 0.3142 0.036 Uiso 1 1 calc R . . C8 C -0.3876(3) 0.6172(2) 0.3868(2) 0.0307(5) Uani 1 1 d . . . H8 H -0.4819 0.6100 0.3902 0.037 Uiso 1 1 calc R . . C9 C -0.2685(3) 0.7461(2) 0.4269(2) 0.0295(5) Uani 1 1 d . . . C10 C -0.1293(3) 0.7566(2) 0.4194(2) 0.0297(5) Uani 1 1 d . . . H10 H -0.0509 0.8435 0.4451 0.036 Uiso 1 1 calc R . . C11 C -0.1063(3) 0.6383(2) 0.3736(2) 0.0285(5) Uani 1 1 d . . . C12 C -0.4154(3) 0.8637(2) 0.4883(2) 0.0390(6) Uani 1 1 d . . . H12A H -0.4978 0.8375 0.3989 0.059 Uiso 1 1 calc R . . H12B H -0.4033 0.9538 0.5333 0.059 Uiso 1 1 calc R . . H12C H -0.4396 0.7958 0.5405 0.059 Uiso 1 1 calc R . . C13 C 0.1476(3) 0.7716(2) 0.3976(3) 0.0430(6) Uani 1 1 d . . . H13A H 0.1112 0.8332 0.3430 0.065 Uiso 1 1 calc R . . H13B H 0.2324 0.7580 0.3820 0.065 Uiso 1 1 calc R . . H13C H 0.1817 0.8119 0.4924 0.065 Uiso 1 1 calc R . . C14 C -0.2984(3) 0.1427(2) 0.21695(19) 0.0260(5) Uani 1 1 d . . . C15 C -0.4298(3) 0.0126(2) 0.17643(19) 0.0255(5) Uani 1 1 d . . . C16 C -0.5703(3) 0.0120(2) 0.17718(19) 0.0278(5) Uani 1 1 d . . . H16 H -0.5788 0.0964 0.2049 0.033 Uiso 1 1 calc R . . C17 C -0.6974(3) -0.1097(2) 0.1382(2) 0.0299(5) Uani 1 1 d . . . H17 H -0.7897 -0.1067 0.1395 0.036 Uiso 1 1 calc R . . C18 C -0.6857(3) -0.2360(2) 0.09724(19) 0.0294(5) Uani 1 1 d . . . C19 C -0.5484(3) -0.2400(2) 0.0939(2) 0.0309(5) Uani 1 1 d . . . H19 H -0.5410 -0.3249 0.0658 0.037 Uiso 1 1 calc R . . C20 C -0.4225(3) -0.1174(2) 0.1324(2) 0.0285(5) Uani 1 1 d . . . C21 C -0.8053(3) -0.4838(2) 0.0197(2) 0.0379(6) Uani 1 1 d . . . H21A H -0.7814 -0.4826 -0.0591 0.057 Uiso 1 1 calc R . . H21B H -0.9026 -0.5569 -0.0025 0.057 Uiso 1 1 calc R . . H21C H -0.7255 -0.5002 0.0925 0.057 Uiso 1 1 calc R . . C22 C -0.2756(3) -0.2368(2) 0.0674(2) 0.0411(6) Uani 1 1 d . . . H22A H -0.2968 -0.3093 0.1159 0.062 Uiso 1 1 calc R . . H22B H -0.1737 -0.2174 0.0697 0.062 Uiso 1 1 calc R . . H22C H -0.3503 -0.2668 -0.0256 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0284(3) 0.0315(3) 0.0366(3) 0.0070(2) 0.0161(2) 0.0124(2) S2 0.0323(3) 0.0339(3) 0.0377(3) 0.0045(2) 0.0154(2) 0.0186(3) O1 0.0341(9) 0.0283(8) 0.0460(9) 0.0008(7) 0.0141(7) 0.0160(7) O2 0.0329(9) 0.0284(8) 0.0565(10) 0.0042(7) 0.0260(8) 0.0084(7) O3 0.0369(9) 0.0259(8) 0.0452(8) 0.0032(7) 0.0176(7) 0.0092(7) O4 0.0397(9) 0.0269(8) 0.0521(9) 0.0050(7) 0.0243(8) 0.0174(7) O5 0.0284(8) 0.0227(8) 0.0332(7) 0.0042(6) 0.0143(6) 0.0118(6) O6 0.0329(9) 0.0471(10) 0.0484(9) 0.0083(8) 0.0206(7) 0.0201(8) C2 0.0336(13) 0.0384(13) 0.0307(11) 0.0096(9) 0.0145(9) 0.0176(11) C3 0.0309(12) 0.0296(11) 0.0280(10) 0.0079(8) 0.0130(9) 0.0159(10) C4 0.0331(12) 0.0269(11) 0.0256(10) 0.0064(8) 0.0123(9) 0.0167(9) C5 0.0264(11) 0.0237(10) 0.0291(10) 0.0077(8) 0.0138(9) 0.0104(9) C6 0.0298(11) 0.0236(11) 0.0265(10) 0.0060(8) 0.0120(9) 0.0126(9) C7 0.0294(12) 0.0249(11) 0.0335(11) 0.0044(9) 0.0115(9) 0.0093(9) C8 0.0273(12) 0.0308(12) 0.0372(11) 0.0042(9) 0.0136(9) 0.0147(10) C9 0.0323(12) 0.0255(11) 0.0290(10) 0.0042(8) 0.0077(9) 0.0143(9) C10 0.0318(12) 0.0231(11) 0.0332(11) 0.0043(9) 0.0132(9) 0.0086(9) C11 0.0291(12) 0.0295(11) 0.0311(10) 0.0071(9) 0.0149(9) 0.0129(9) C12 0.0383(13) 0.0370(13) 0.0469(13) 0.0032(10) 0.0165(11) 0.0229(11) C13 0.0359(14) 0.0353(13) 0.0591(15) 0.0039(11) 0.0263(12) 0.0072(11) C14 0.0326(12) 0.0234(10) 0.0268(10) 0.0048(8) 0.0135(9) 0.0149(9) C15 0.0318(12) 0.0270(11) 0.0232(9) 0.0078(8) 0.0127(9) 0.0153(9) C16 0.0337(12) 0.0251(11) 0.0281(10) 0.0056(8) 0.0131(9) 0.0146(9) C17 0.0301(12) 0.0309(12) 0.0301(10) 0.0050(9) 0.0121(9) 0.0134(10) C18 0.0354(13) 0.0238(11) 0.0271(10) 0.0049(8) 0.0116(9) 0.0095(10) C19 0.0420(13) 0.0236(11) 0.0294(10) 0.0059(8) 0.0140(10) 0.0153(10) C20 0.0357(12) 0.0260(11) 0.0292(10) 0.0077(8) 0.0147(9) 0.0157(10) C21 0.0473(15) 0.0227(11) 0.0425(12) 0.0036(9) 0.0195(11) 0.0103(11) C22 0.0485(15) 0.0346(13) 0.0493(13) 0.0006(10) 0.0254(12) 0.0223(12) _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 C3 1.741(2) . ? S1 C2 1.766(2) . ? S2 C4 1.743(2) . ? S2 C2 1.776(3) . ? O1 C9 1.367(3) . ? O1 C12 1.414(3) . ? O2 C11 1.355(3) . ? O2 C13 1.422(3) . ? O3 C18 1.366(3) . ? O3 C21 1.427(3) . ? O4 C20 1.364(3) . ? O4 C22 1.431(2) . ? O5 C5 1.381(3) . ? O5 C14 1.386(2) . ? O6 C2 1.213(3) . ? C3 C5 1.368(3) . ? C3 C4 1.430(3) . ? C4 C14 1.368(3) . ? C5 C6 1.463(3) . ? C6 C7 1.387(3) . ? C6 C11 1.412(3) . ? C7 C8 1.391(3) . ? C8 C9 1.390(3) . ? C9 C10 1.385(3) . ? C10 C11 1.384(3) . ? C14 C15 1.457(3) . ? C15 C16 1.393(3) . ? C15 C20 1.410(3) . ? C16 C17 1.383(3) . ? C17 C18 1.386(3) . ? C18 C19 1.387(3) . ? C19 C20 1.383(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C2 95.68(11) . . ? C4 S2 C2 95.42(11) . . ? C9 O1 C12 116.98(19) . . ? C11 O2 C13 118.39(17) . . ? C18 O3 C21 117.37(18) . . ? C20 O4 C22 118.53(19) . . ? C5 O5 C14 109.61(17) . . ? O6 C2 S1 122.40(19) . . ? O6 C2 S2 122.10(18) . . ? S1 C2 S2 115.50(13) . . ? C5 C3 C4 107.6(2) . . ? C5 C3 S1 135.65(17) . . ? C4 C3 S1 116.73(16) . . ? C14 C4 C3 107.74(19) . . ? C14 C4 S2 135.58(17) . . ? C3 C4 S2 116.67(17) . . ? C3 C5 O5 107.59(18) . . ? C3 C5 C6 139.1(2) . . ? O5 C5 C6 113.29(18) . . ? C7 C6 C11 117.57(19) . . ? C7 C6 C5 120.48(19) . . ? C11 C6 C5 121.95(19) . . ? C6 C7 C8 122.5(2) . . ? C7 C8 C9 118.6(2) . . ? O1 C9 C10 114.9(2) . . ? O1 C9 C8 124.6(2) . . ? C10 C9 C8 120.48(19) . . ? C11 C10 C9 120.3(2) . . ? O2 C11 C10 123.6(2) . . ? O2 C11 C6 115.80(18) . . ? C10 C11 C6 120.6(2) . . ? C4 C14 O5 107.43(18) . . ? C4 C14 C15 139.65(19) . . ? O5 C14 C15 112.92(18) . . ? C16 C15 C20 116.9(2) . . ? C16 C15 C14 121.03(18) . . ? C20 C15 C14 122.0(2) . . ? C17 C16 C15 122.3(2) . . ? C16 C17 C18 119.3(2) . . ? O3 C18 C17 116.3(2) . . ? O3 C18 C19 123.40(19) . . ? C17 C18 C19 120.3(2) . . ? C20 C19 C18 119.76(19) . . ? O4 C20 C19 123.07(19) . . ? O4 C20 C15 115.51(19) . . ? C19 C20 C15 121.4(2) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.466 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.061 #===END data_complex_8d.TCNQ _database_code_CSD 213285 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 N2 O5 S3' _chemical_formula_weight 548.63 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9335(16) _cell_length_b 11.415(2) _cell_length_c 14.062(3) _cell_angle_alpha 76.79(3) _cell_angle_beta 83.82(3) _cell_angle_gamma 89.09(3) _cell_volume 1232.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9664 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18131 _diffrn_reflns_av_R_equivalents 0.1164 _diffrn_reflns_av_sigmaI/netI 0.1358 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5515 _reflns_number_gt 3078 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0674P)^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 5515 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1334 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.003 _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 C17 C -0.2554(4) -0.2783(3) 0.3745(2) 0.0250(7) Uani 1 1 d . . . C22 C 0.3879(4) 0.1889(3) 0.3991(2) 0.0297(8) Uani 1 1 d . . . C23 C 0.1458(4) 0.3214(3) 0.3944(2) 0.0265(7) Uani 1 1 d . . . C24 C 0.2084(4) 0.2012(3) 0.4166(2) 0.0258(7) Uani 1 1 d . . . C25 C 0.1044(4) 0.1016(3) 0.4571(2) 0.0243(7) Uani 1 1 d . . . C26 C 0.1754(4) -0.0160(3) 0.4824(2) 0.0260(7) Uani 1 1 d . . . C27 C -0.0758(4) 0.1138(3) 0.4763(2) 0.0262(7) Uani 1 1 d . . . N1 N 0.5327(4) 0.1782(3) 0.3863(2) 0.0445(8) Uani 1 1 d . . . N2 N 0.0983(4) 0.4188(3) 0.3774(2) 0.0357(7) Uani 1 1 d . . . C1 C 0.5010(4) 0.1243(3) 0.1158(2) 0.0287(8) Uani 1 1 d . . . C2 C 0.2073(4) 0.1986(3) 0.1748(2) 0.0237(7) Uani 1 1 d . . . C3 C 0.2003(4) 0.0703(3) 0.2061(2) 0.0236(7) Uani 1 1 d . . . C4 C 0.0389(4) 0.0381(3) 0.2488(2) 0.0249(7) Uani 1 1 d . . . C5 C 0.0473(4) 0.2406(3) 0.1984(2) 0.0240(7) Uani 1 1 d . . . C6 C -0.0420(4) 0.3547(3) 0.1826(2) 0.0246(7) Uani 1 1 d . . . C7 C 0.0402(4) 0.4650(3) 0.1423(2) 0.0272(8) Uani 1 1 d . . . C8 C -0.0490(4) 0.5728(3) 0.1247(2) 0.0286(8) Uani 1 1 d . . . H8 H 0.0087 0.6468 0.0956 0.034 Uiso 1 1 calc R . . C9 C -0.2239(4) 0.5706(3) 0.1502(2) 0.0277(8) Uani 1 1 d . . . C10 C -0.3078(4) 0.4624(3) 0.1913(2) 0.0301(8) Uani 1 1 d . . . H10 H -0.4269 0.4612 0.2087 0.036 Uiso 1 1 calc R . . C11 C -0.2177(4) 0.3562(3) 0.2069(2) 0.0267(7) Uani 1 1 d . . . H11 H -0.2765 0.2825 0.2349 0.032 Uiso 1 1 calc R . . C12 C 0.2998(4) 0.5674(3) 0.0661(3) 0.0345(8) Uani 1 1 d . . . H12A H 0.2523 0.5938 0.0033 0.052 Uiso 1 1 calc R . . H12B H 0.4206 0.5500 0.0540 0.052 Uiso 1 1 calc R . . H12C H 0.2863 0.6311 0.1026 0.052 Uiso 1 1 calc R . . C13 C -0.2412(5) 0.7853(3) 0.0988(3) 0.0377(9) Uani 1 1 d . . . H13A H -0.1619 0.7998 0.1437 0.056 Uiso 1 1 calc R . . H13B H -0.3268 0.8486 0.0914 0.056 Uiso 1 1 calc R . . H13C H -0.1791 0.7859 0.0345 0.056 Uiso 1 1 calc R . . C14 C -0.0594(4) -0.0706(3) 0.2917(2) 0.0238(7) Uani 1 1 d . . . C15 C 0.0145(4) -0.1851(3) 0.3105(2) 0.0239(7) Uani 1 1 d . . . C16 C -0.0811(4) -0.2891(3) 0.3513(2) 0.0259(7) Uani 1 1 d . . . H16 H -0.0288 -0.3658 0.3632 0.031 Uiso 1 1 calc R . . C18 C -0.3319(4) -0.1662(3) 0.3560(2) 0.0274(7) Uani 1 1 d . . . H18 H -0.4509 -0.1598 0.3709 0.033 Uiso 1 1 calc R . . C19 C -0.2352(4) -0.0644(3) 0.3161(2) 0.0255(7) Uani 1 1 d . . . H19 H -0.2886 0.0119 0.3048 0.031 Uiso 1 1 calc R . . C20 C 0.2709(4) -0.2996(3) 0.3006(3) 0.0336(8) Uani 1 1 d . . . H20A H 0.2709 -0.3334 0.3713 0.050 Uiso 1 1 calc R . . H20B H 0.3880 -0.2876 0.2698 0.050 Uiso 1 1 calc R . . H20C H 0.2122 -0.3552 0.2713 0.050 Uiso 1 1 calc R . . C21 C -0.2897(4) -0.4918(3) 0.4299(3) 0.0328(8) Uani 1 1 d . . . H21A H -0.2321 -0.5037 0.3676 0.049 Uiso 1 1 calc R . . H21B H -0.3799 -0.5523 0.4538 0.049 Uiso 1 1 calc R . . H21C H -0.2078 -0.5000 0.4784 0.049 Uiso 1 1 calc R . . O1 O 0.2123(3) 0.46068(18) 0.12256(17) 0.0330(6) Uani 1 1 d . . . O2 O -0.3224(3) 0.67097(19) 0.13751(17) 0.0346(6) Uani 1 1 d . . . O3 O 0.1856(3) -0.18692(18) 0.28545(17) 0.0313(6) Uani 1 1 d . . . O4 O -0.3613(3) -0.37454(19) 0.41500(17) 0.0336(6) Uani 1 1 d . . . S1 S 0.69560(11) 0.11731(8) 0.06396(7) 0.0370(3) Uani 1 1 d . . . S2 S 0.39848(10) 0.26087(7) 0.11499(6) 0.0270(2) Uani 1 1 d . . . S3 S 0.38516(10) -0.00387(7) 0.17686(6) 0.0288(2) Uani 1 1 d . . . O5 O -0.0522(2) 0.14327(17) 0.24467(15) 0.0251(5) Uani 1 1 d . . . H27 H -0.135(3) 0.191(2) 0.4580(19) 0.010(7) Uiso 1 1 d . . . H26 H 0.295(4) -0.029(3) 0.477(2) 0.025(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 C17 0.0309(18) 0.0230(17) 0.0189(18) -0.0018(14) 0.0004(14) -0.0027(15) C22 0.040(2) 0.0210(18) 0.0242(19) 0.0011(14) 0.0004(16) 0.0006(16) C23 0.0292(18) 0.027(2) 0.0232(19) -0.0077(15) 0.0008(14) -0.0036(15) C24 0.0314(18) 0.0231(18) 0.0229(19) -0.0049(14) -0.0035(14) 0.0050(15) C25 0.0319(18) 0.0231(17) 0.0188(18) -0.0060(13) -0.0043(14) 0.0047(14) C26 0.0248(18) 0.0276(19) 0.026(2) -0.0079(15) -0.0009(14) 0.0032(16) C27 0.0322(19) 0.0200(17) 0.0261(19) -0.0048(14) -0.0050(14) 0.0101(15) N1 0.0368(19) 0.0388(19) 0.047(2) 0.0055(15) 0.0092(15) 0.0022(15) N2 0.0450(18) 0.0277(17) 0.0332(18) -0.0048(14) -0.0026(14) -0.0008(14) C1 0.0368(19) 0.0288(19) 0.0211(19) -0.0061(15) -0.0053(15) 0.0014(15) C2 0.0309(18) 0.0207(17) 0.0192(18) -0.0038(13) -0.0036(14) 0.0022(14) C3 0.0298(18) 0.0206(16) 0.0201(18) -0.0040(13) -0.0022(14) 0.0007(14) C4 0.0307(18) 0.0220(17) 0.0215(18) -0.0043(14) -0.0029(14) 0.0044(14) C5 0.0302(18) 0.0201(17) 0.0200(18) -0.0017(13) -0.0009(13) -0.0037(14) C6 0.0333(18) 0.0210(17) 0.0183(18) -0.0015(13) -0.0043(14) 0.0021(14) C7 0.0318(19) 0.0274(18) 0.0214(19) -0.0040(14) -0.0019(14) 0.0003(15) C8 0.041(2) 0.0200(17) 0.0231(19) -0.0019(14) -0.0027(15) 0.0015(15) C9 0.0374(19) 0.0238(18) 0.0237(19) -0.0082(14) -0.0060(15) 0.0072(15) C10 0.0319(18) 0.034(2) 0.025(2) -0.0078(15) -0.0040(15) 0.0054(16) C11 0.0339(18) 0.0202(17) 0.0247(19) -0.0034(14) -0.0005(14) -0.0009(15) C12 0.038(2) 0.0266(19) 0.035(2) -0.0021(16) 0.0046(16) -0.0062(16) C13 0.053(2) 0.0221(19) 0.040(2) -0.0076(16) -0.0110(18) 0.0076(17) C14 0.0307(18) 0.0205(17) 0.0184(17) -0.0014(13) -0.0013(14) 0.0002(14) C15 0.0277(17) 0.0239(18) 0.0197(18) -0.0055(14) -0.0002(14) 0.0002(14) C16 0.0353(19) 0.0195(17) 0.0225(18) -0.0045(14) -0.0027(14) 0.0029(15) C18 0.0275(18) 0.0277(18) 0.0254(19) -0.0035(14) -0.0018(14) -0.0006(15) C19 0.0327(18) 0.0201(17) 0.0232(19) -0.0039(14) -0.0027(14) 0.0034(14) C20 0.0316(19) 0.0262(19) 0.041(2) -0.0064(16) 0.0021(16) 0.0050(15) C21 0.042(2) 0.0235(18) 0.031(2) -0.0035(15) 0.0018(16) -0.0045(16) O1 0.0313(13) 0.0207(12) 0.0406(15) 0.0031(10) 0.0028(11) -0.0012(10) O2 0.0400(14) 0.0232(13) 0.0402(15) -0.0065(11) -0.0049(11) 0.0063(11) O3 0.0287(13) 0.0195(12) 0.0406(15) -0.0004(10) 0.0050(10) 0.0009(10) O4 0.0335(13) 0.0222(12) 0.0404(15) -0.0008(10) 0.0031(11) -0.0003(10) S1 0.0353(5) 0.0295(5) 0.0417(6) -0.0041(4) 0.0066(4) 0.0018(4) S2 0.0307(5) 0.0216(4) 0.0264(5) -0.0027(3) 0.0006(4) -0.0004(4) S3 0.0309(5) 0.0214(4) 0.0316(5) -0.0033(4) 0.0018(4) 0.0017(4) O5 0.0296(12) 0.0194(12) 0.0240(13) -0.0027(9) 0.0015(9) 0.0010(10) _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 C17 O4 1.370(4) . ? C17 C18 1.389(4) . ? C17 C16 1.397(4) . ? C22 N1 1.152(4) . ? C22 C24 1.429(5) . ? C23 N2 1.149(4) . ? C23 C24 1.428(4) . ? C24 C25 1.389(4) . ? C25 C26 1.431(4) . ? C25 C27 1.437(4) . ? C26 C27 1.356(4) 2_556 ? C27 C26 1.356(4) 2_556 ? C1 S1 1.644(3) . ? C1 S3 1.738(3) . ? C1 S2 1.745(3) . ? C2 C5 1.383(4) . ? C2 C3 1.430(4) . ? C2 S2 1.732(3) . ? C3 C4 1.372(4) . ? C3 S3 1.740(3) . ? C4 O5 1.385(4) . ? C4 C14 1.449(4) . ? C5 O5 1.366(4) . ? C5 C6 1.456(4) . ? C6 C7 1.397(4) . ? C6 C11 1.400(4) . ? C7 O1 1.366(4) . ? C7 C8 1.396(4) . ? C8 C9 1.395(4) . ? C9 O2 1.365(4) . ? C9 C10 1.385(4) . ? C10 C11 1.383(4) . ? C12 O1 1.436(4) . ? C13 O2 1.429(4) . ? C14 C15 1.405(4) . ? C14 C19 1.404(4) . ? C15 O3 1.367(4) . ? C15 C16 1.392(4) . ? C18 C19 1.375(4) . ? C20 O3 1.427(4) . ? C21 O4 1.425(4) . ? 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 C17 C18 116.0(3) . . ? O4 C17 C16 123.4(3) . . ? C18 C17 C16 120.6(3) . . ? N1 C22 C24 179.1(4) . . ? N2 C23 C24 178.5(3) . . ? C25 C24 C23 123.0(3) . . ? C25 C24 C22 121.0(3) . . ? C23 C24 C22 115.9(3) . . ? C24 C25 C26 120.5(3) . . ? C24 C25 C27 121.2(3) . . ? C26 C25 C27 118.3(3) . . ? C27 C26 C25 121.2(3) 2_556 . ? C26 C27 C25 120.6(3) 2_556 . ? S1 C1 S3 122.1(2) . . ? S1 C1 S2 122.23(19) . . ? S3 C1 S2 115.62(19) . . ? C5 C2 C3 107.1(3) . . ? C5 C2 S2 136.4(2) . . ? C3 C2 S2 116.4(2) . . ? C4 C3 C2 107.9(3) . . ? C4 C3 S3 136.6(2) . . ? C2 C3 S3 115.4(2) . . ? C3 C4 O5 107.1(3) . . ? C3 C4 C14 138.7(3) . . ? O5 C4 C14 114.2(3) . . ? O5 C5 C2 107.6(3) . . ? O5 C5 C6 114.3(3) . . ? C2 C5 C6 138.0(3) . . ? C7 C6 C11 117.5(3) . . ? C7 C6 C5 122.7(3) . . ? C11 C6 C5 119.8(3) . . ? O1 C7 C8 122.4(3) . . ? O1 C7 C6 116.0(3) . . ? C8 C7 C6 121.6(3) . . ? C9 C8 C7 119.1(3) . . ? O2 C9 C10 116.0(3) . . ? O2 C9 C8 123.8(3) . . ? C10 C9 C8 120.2(3) . . ? C11 C10 C9 119.9(3) . . ? C10 C11 C6 121.6(3) . . ? C15 C14 C19 117.3(3) . . ? C15 C14 C4 122.3(3) . . ? C19 C14 C4 120.3(3) . . ? O3 C15 C16 122.7(3) . . ? O3 C15 C14 115.3(3) . . ? C16 C15 C14 122.0(3) . . ? C15 C16 C17 118.6(3) . . ? C19 C18 C17 120.0(3) . . ? C18 C19 C14 121.6(3) . . ? C7 O1 C12 118.2(2) . . ? C9 O2 C13 118.2(3) . . ? C15 O3 C20 119.1(2) . . ? C17 O4 C21 117.7(2) . . ? C2 S2 C1 96.02(15) . . ? C1 S3 C3 96.38(15) . . ? C5 O5 C4 110.3(2) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.419 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.097 #===END