# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/242 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Skabara, Peter J.' 'Berridge, Rory' 'Prescott, Karen' 'Goldenberg, Leonid M.' 'Orti, Enrique' 'Viruela, Rafael' 'Pou-Amrigo, Rosendo' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' 'Coles, Simon J.' 'Hursthouse, Michael B.' _journal_name_full 'Journal of Materials Science' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2000' _ccdc_journal_depnumber '?' _publ_section_title ; Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives. ; #===================================================================END data_9 _audit_creation_method SHELXL _chemical_name_systematic ; thieno[3',4'-d:5,6][1,4]dithiino[2,3-b]quinoxaline ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H6 N2 S3' _chemical_formula_weight 274.37 _chemical_melting_point '161-163 deg.C' _chemical_compound_source ? _ccdc_compound_id '9' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; none ; _ccdc_comments '?' 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' '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 6.876(2) _cell_length_b 9.361(3) _cell_length_c 9.508(3) _cell_angle_alpha 101.96(1) _cell_angle_beta 95.96(1) _cell_angle_gamma 104.09(1) _cell_volume 573.0(1) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 511 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 23.2 _exptl_crystal_description 'pinakoid' _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method ? _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.7644 _exptl_absorpt_correction_T_max 0.8689 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.1300 0.00 0.00 -1.00 0.1300 1.00 0.00 0.00 0.2000 -1.00 0.00 0.00 0.2000 0.00 1.00 0.00 0.2100 0.00 -1.00 0.00 0.2100 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of exposures; each set had a different \f and/or 2\q angles and each exposure covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing duplicate reflections. Crystal to detector distance 4.51 cm. ; _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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 3221 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1793 _reflns_number_observed 1693 _reflns_observed_criterion I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL-PLUS' _computing_publication_material 'SHELXL-93' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 7 with very negative F^2^. Weighted R-factors, wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.42P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0185(40) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1786 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_obs 0.0286 _refine_ls_wR_factor_all 0.0819 _refine_ls_wR_factor_obs 0.0764 _refine_ls_goodness_of_fit_all 1.121 _refine_ls_goodness_of_fit_obs 1.119 _refine_ls_restrained_S_all 1.162 _refine_ls_restrained_S_obs 1.119 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S -0.25913(9) 0.01631(6) 0.41275(6) 0.0336(2) Uani 1 d . . S2 S 0.20160(9) 0.12753(6) 0.15503(6) 0.0311(2) Uani 1 d . . S3 S 0.22805(9) 0.40928(6) 0.44047(5) 0.0319(2) Uani 1 d . . N1 N 0.2234(2) 0.3361(2) 0.0064(2) 0.0252(4) Uani 1 d . . C2 C 0.2172(3) 0.3149(2) 0.1376(2) 0.0240(4) Uani 1 d . . C3 C 0.2372(3) 0.4386(2) 0.2622(2) 0.0247(4) Uani 1 d . . N4 N 0.2719(3) 0.5791(2) 0.2511(2) 0.0258(4) Uani 1 d . . C5 C 0.3176(3) 0.7544(2) 0.0954(2) 0.0291(5) Uani 1 d . . H5 H 0.3307(38) 0.8341(29) 0.1802(29) 0.043(7) Uiso 1 d . . C6 C 0.3218(3) 0.7795(3) -0.0407(2) 0.0312(5) Uani 1 d . . H6 H 0.3401(37) 0.8792(30) -0.0557(27) 0.038(6) Uiso 1 d . . C7 C 0.2931(3) 0.6572(3) -0.1643(2) 0.0315(5) Uani 1 d . . H7 H 0.2986(38) 0.6784(28) -0.2562(29) 0.039(7) Uiso 1 d . . C8 C 0.2613(3) 0.5114(3) -0.1484(2) 0.0283(5) Uani 1 d . . H8 H 0.2407(37) 0.4262(28) -0.2293(28) 0.037(6) Uiso 1 d . . C9 C 0.2556(3) 0.4825(2) -0.0085(2) 0.0239(4) Uani 1 d . . C10 C 0.2833(3) 0.6048(2) 0.1151(2) 0.0242(4) Uani 1 d . . C12 C -0.1264(3) -0.0124(3) 0.2705(2) 0.0306(5) Uani 1 d . . H12 H -0.1642(35) -0.1024(28) 0.2002(26) 0.032(6) Uiso 1 d . . C13 C 0.0284(3) 0.1127(2) 0.2790(2) 0.0259(5) Uani 1 d . . C14 C 0.0390(3) 0.2346(2) 0.4009(2) 0.0260(5) Uani 1 d . . C15 C -0.1101(3) 0.1994(2) 0.4814(2) 0.0301(5) Uani 1 d . . H15 H -0.1369(41) 0.2583(31) 0.5615(30) 0.048(7) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0391(3) 0.0321(3) 0.0302(3) 0.0084(2) 0.0120(2) 0.0074(2) S2 0.0415(3) 0.0235(3) 0.0327(3) 0.0054(2) 0.0169(2) 0.0133(2) S3 0.0420(3) 0.0280(3) 0.0199(3) 0.0011(2) 0.0033(2) 0.0034(2) N1 0.0237(9) 0.0263(9) 0.0240(9) 0.0023(7) 0.0044(7) 0.0066(7) C2 0.0233(10) 0.0238(10) 0.0237(11) 0.0019(8) 0.0056(8) 0.0064(8) C3 0.0242(10) 0.0263(11) 0.0229(10) 0.0024(8) 0.0048(8) 0.0080(8) N4 0.0265(9) 0.0252(9) 0.0245(9) 0.0019(7) 0.0051(7) 0.0078(7) C5 0.0295(11) 0.0249(11) 0.0326(12) 0.0037(9) 0.0062(9) 0.0096(9) C6 0.0287(11) 0.0289(12) 0.0390(13) 0.0116(9) 0.0059(9) 0.0105(9) C7 0.0285(11) 0.0399(13) 0.0286(12) 0.0130(10) 0.0021(9) 0.0111(9) C8 0.0254(11) 0.0337(12) 0.0229(11) 0.0034(9) 0.0008(8) 0.0072(9) C9 0.0186(10) 0.0259(10) 0.0256(11) 0.0031(8) 0.0026(8) 0.0061(8) C10 0.0205(10) 0.0270(11) 0.0249(11) 0.0040(8) 0.0037(8) 0.0078(8) C12 0.0397(12) 0.0264(11) 0.0258(11) 0.0044(9) 0.0082(9) 0.0098(10) C13 0.0317(11) 0.0245(10) 0.0234(10) 0.0062(8) 0.0061(8) 0.0103(9) C14 0.0325(11) 0.0246(11) 0.0210(10) 0.0046(8) 0.0033(8) 0.0095(9) C15 0.0402(12) 0.0296(11) 0.0226(11) 0.0046(9) 0.0083(9) 0.0134(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 S1 C15 1.720(2) . ? S1 C12 1.721(2) . ? S2 C13 1.763(2) . ? S2 C2 1.775(2) . ? S3 C14 1.765(2) . ? S3 C3 1.778(2) . ? N1 C2 1.307(3) . ? N1 C9 1.374(3) . ? C2 C3 1.444(3) . ? C3 N4 1.308(3) . ? N4 C10 1.371(3) . ? C5 C6 1.365(3) . ? C5 C10 1.418(3) . ? C6 C7 1.420(3) . ? C7 C8 1.372(3) . ? C8 C9 1.414(3) . ? C9 C10 1.421(3) . ? C12 C13 1.360(3) . ? C13 C14 1.430(3) . ? C14 C15 1.360(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 C15 S1 C12 92.39(11) . . ? C13 S2 C2 99.60(9) . . ? C14 S3 C3 100.31(9) . . ? C2 N1 C9 117.3(2) . . ? N1 C2 C3 122.0(2) . . ? N1 C2 S2 115.86(14) . . ? C3 C2 S2 122.00(15) . . ? N4 C3 C2 121.8(2) . . ? N4 C3 S3 116.30(15) . . ? C2 C3 S3 121.9(2) . . ? C3 N4 C10 117.4(2) . . ? C6 C5 C10 120.2(2) . . ? C5 C6 C7 120.8(2) . . ? C8 C7 C6 120.2(2) . . ? C7 C8 C9 120.0(2) . . ? N1 C9 C8 119.6(2) . . ? N1 C9 C10 120.7(2) . . ? C8 C9 C10 119.8(2) . . ? N4 C10 C5 120.1(2) . . ? N4 C10 C9 120.9(2) . . ? C5 C10 C9 119.0(2) . . ? C13 C12 S1 110.8(2) . . ? C12 C13 C14 113.0(2) . . ? C12 C13 S2 124.7(2) . . ? C14 C13 S2 122.3(2) . . ? C15 C14 C13 112.5(2) . . ? C15 C14 S3 124.8(2) . . ? C13 C14 S3 122.7(2) . . ? C14 C15 S1 111.2(2) . . ? _refine_diff_density_max 0.349 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.052 #==========================================================END data_9:TCNQ _audit_creation_method SHELXL-97 _chemical_name_systematic ; thieno[3',4'-d:5,6][1,4]dithiino[2,3-b]quinoxaline tetracyanoquinodimethane ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H6 N2 S3,C12 H4 N4' _chemical_formula_sum 'C24 H10 N6 S3' _chemical_formula_weight 478.56 _ccdc_compound_id '9:TCNQ' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; none ; _ccdc_comments '?' 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' '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 8.059(1) _cell_length_b 12.144(1) _cell_length_c 22.257(2) _cell_angle_alpha 76.95(1) _cell_angle_beta 85.24(1) _cell_angle_gamma 79.67(1) _cell_volume 2085.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 724 _cell_measurement_theta_min 11.0 _cell_measurement_theta_max 26.0 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9310 _exptl_absorpt_correction_T_max 0.9723 _exptl_absorpt_process_details 'XPREP (SHELXTL) program' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.0400 0.00 0.00 1.00 0.0400 0.00 -1.00 -1.00 0.0750 0.00 1.00 1.00 0.0750 -1.00 0.00 0.00 0.1000 1.00 0.00 0.00 0.1000 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of exposures; each set had a different \f and/or 2\q angles and each exposure (45 s) covered 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 11556 _diffrn_reflns_av_R_equivalents 0.1159 _diffrn_reflns_av_sigmaI/netI 0.1034 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 0.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7307 _reflns_number_gt 5078 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0817P)^2^+3.6213P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7307 _refine_ls_number_parameters 595 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1928 _refine_ls_wR_factor_gt 0.1594 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1A S 0.36069(15) 0.24635(11) -0.08400(5) 0.0221(3) Uani 1 1 d . . . S2A S 0.45693(15) 0.38887(10) 0.06435(5) 0.0188(3) Uani 1 1 d . . . S3A S 0.69625(15) 0.11391(10) 0.06228(5) 0.0210(3) Uani 1 1 d . . . N1A N 0.5802(5) 0.3472(3) 0.17116(18) 0.0177(8) Uani 1 1 d . . . C2A C 0.5798(5) 0.2993(4) 0.1238(2) 0.0155(9) Uani 1 1 d . . . C3A C 0.6761(6) 0.1875(4) 0.1226(2) 0.0174(10) Uani 1 1 d . . . N4A N 0.7721(5) 0.1303(3) 0.16880(18) 0.0180(8) Uani 1 1 d . . . C5A C 0.8759(6) 0.1217(4) 0.2683(2) 0.0215(10) Uani 1 1 d . . . H5A H 0.9415 0.0486 0.2678 0.026 Uiso 1 1 d R . . C6A C 0.8793(6) 0.1712(5) 0.3181(2) 0.0256(11) Uani 1 1 d . . . H6A H 0.9464 0.1320 0.3520 0.031 Uiso 1 1 d R . . C7A C 0.7817(6) 0.2817(5) 0.3184(2) 0.0258(11) Uani 1 1 d . . . H7A H 0.7845 0.3152 0.3529 0.031 Uiso 1 1 d R . . C8A C 0.6854(6) 0.3391(5) 0.2708(2) 0.0242(11) Uani 1 1 d . . . H8A H 0.6223 0.4128 0.2717 0.029 Uiso 1 1 d R . . C9A C 0.6786(6) 0.2893(4) 0.2193(2) 0.0189(10) Uani 1 1 d . . . C10A C 0.7752(6) 0.1798(4) 0.2183(2) 0.0158(9) Uani 1 1 d . . . C12A C 0.3427(6) 0.3428(4) -0.0376(2) 0.0193(10) Uani 1 1 d . . . H12A H 0.2691 0.4145 -0.0445 0.023 Uiso 1 1 d R . . C13A C 0.4488(6) 0.3039(4) 0.0111(2) 0.0182(10) Uani 1 1 d . . . C14A C 0.5452(6) 0.1931(4) 0.0100(2) 0.0153(9) Uani 1 1 d . . . C15A C 0.5081(6) 0.1519(4) -0.0390(2) 0.0177(10) Uani 1 1 d . . . H16A H 0.5584 0.0794 -0.0469 0.021 Uiso 1 1 d R . . S1B S 0.50383(16) 0.74835(11) 0.52637(6) 0.0234(3) Uani 1 1 d . . . S2B S 0.25321(15) 0.88281(10) 0.35882(5) 0.0193(3) Uani 1 1 d . . . S3B S 0.48499(15) 0.59947(10) 0.37227(5) 0.0206(3) Uani 1 1 d . . . N1B N 0.1772(5) 0.8447(3) 0.25653(17) 0.0171(8) Uani 1 1 d . . . C2B C 0.2684(5) 0.7949(4) 0.3051(2) 0.0145(9) Uani 1 1 d . . . C3B C 0.3665(6) 0.6817(4) 0.3098(2) 0.0162(9) Uani 1 1 d . . . N4B N 0.3757(5) 0.6274(3) 0.26403(18) 0.0191(8) Uani 1 1 d . . . C5B C 0.2933(6) 0.6222(4) 0.1639(2) 0.0230(11) Uani 1 1 d . . . H5B H 0.3628 0.5496 0.1658 0.028 Uiso 1 1 d R . . C6B C 0.1987(7) 0.6744(5) 0.1122(2) 0.0266(11) Uani 1 1 d . . . H6B H 0.2021 0.6370 0.0788 0.032 Uiso 1 1 d R . . C7B C 0.0978(6) 0.7838(5) 0.1096(2) 0.0253(11) Uani 1 1 d . . . H7B H 0.0346 0.8190 0.0741 0.030 Uiso 1 1 d R . . C8B C 0.0890(6) 0.8399(4) 0.1568(2) 0.0230(11) Uani 1 1 d . . . H8B H 0.0202 0.9129 0.1539 0.028 Uiso 1 1 d R . . C9B C 0.1823(6) 0.7890(4) 0.2095(2) 0.0195(10) Uani 1 1 d . . . C10B C 0.2840(6) 0.6789(4) 0.2135(2) 0.0172(10) Uani 1 1 d . . . C12B C 0.3796(6) 0.8424(4) 0.4725(2) 0.0215(10) Uani 1 1 d . . . H12B H 0.3241 0.9158 0.4777 0.026 Uiso 1 1 d R . . C13B C 0.3687(6) 0.8006(4) 0.4212(2) 0.0169(9) Uani 1 1 d . . . C14B C 0.4657(5) 0.6863(4) 0.4266(2) 0.0154(9) Uani 1 1 d . . . C15B C 0.5458(6) 0.6504(4) 0.4813(2) 0.0163(9) Uani 1 1 d . . . H15B H 0.6171 0.5784 0.4927 0.020 Uiso 1 1 d R . . C1C C 0.2639(5) 0.2392(4) 0.2568(2) 0.0160(9) Uani 1 1 d . . . C2C C 0.3195(5) 0.1421(4) 0.2281(2) 0.0166(10) Uani 1 1 d . . . H2C H 0.3963 0.0786 0.2486 0.020 Uiso 1 1 d R . . C3C C 0.2644(6) 0.1405(4) 0.1729(2) 0.0172(10) Uani 1 1 d . . . H3C H 0.3015 0.0755 0.1553 0.021 Uiso 1 1 d R . . C4C C 0.1491(6) 0.2366(4) 0.1400(2) 0.0186(10) Uani 1 1 d . . . C5C C 0.0978(6) 0.3353(4) 0.1674(2) 0.0163(9) Uani 1 1 d . . . H5C H 0.0248 0.4002 0.1461 0.020 Uiso 1 1 d R . . C6C C 0.1524(6) 0.3361(4) 0.2227(2) 0.0156(9) Uani 1 1 d U . . H6C H 0.1172 0.4019 0.2399 0.019 Uiso 1 1 d R . . C7C C 0.3151(5) 0.2375(4) 0.3146(2) 0.0161(9) Uani 1 1 d . . . C8C C 0.0888(5) 0.2338(4) 0.0840(2) 0.0150(9) Uani 1 1 d . . . C9C C 0.4298(6) 0.1442(4) 0.3486(2) 0.0148(9) Uani 1 1 d . . . C10C C 0.2532(6) 0.3312(4) 0.3457(2) 0.0190(10) Uani 1 1 d . . . C11C C 0.1331(6) 0.1353(4) 0.0572(2) 0.0179(10) Uani 1 1 d . . . C12C C -0.0242(6) 0.3282(4) 0.0506(2) 0.0183(10) Uani 1 1 d . . . N9C N 0.5217(5) 0.0721(4) 0.37584(18) 0.0216(9) Uani 1 1 d . . . N10C N 0.2033(5) 0.4015(3) 0.37086(19) 0.0232(9) Uani 1 1 d . . . N11C N 0.1644(5) 0.0558(4) 0.0349(2) 0.0251(9) Uani 1 1 d . . . N12C N -0.1162(6) 0.4024(4) 0.02299(19) 0.0264(10) Uani 1 1 d . . . C1D C -0.1771(6) 0.7460(4) 0.3105(2) 0.0159(9) Uani 1 1 d . . . C2D C -0.0617(6) 0.6505(4) 0.3432(2) 0.0176(10) Uani 1 1 d . . . H2D H -0.0218 0.5867 0.3249 0.021 Uiso 1 1 d R . . C3D C -0.0100(5) 0.6500(4) 0.3991(2) 0.0163(9) Uani 1 1 d . . . H3D H 0.0663 0.5861 0.4196 0.020 Uiso 1 1 d R . . C4D C -0.0684(6) 0.7452(4) 0.4287(2) 0.0163(9) Uani 1 1 d . . . C5D C -0.1834(6) 0.8420(4) 0.3958(2) 0.0189(10) Uani 1 1 d . . . H5D H -0.2231 0.9059 0.4140 0.023 Uiso 1 1 d R . . C6D C -0.2342(5) 0.8420(4) 0.3398(2) 0.0176(10) Uani 1 1 d . . . H6D H -0.3092 0.9063 0.3191 0.021 Uiso 1 1 d R . . C7D C -0.2324(6) 0.7446(4) 0.2539(2) 0.0171(10) Uani 1 1 d . . . C8D C -0.0182(6) 0.7429(4) 0.4868(2) 0.0167(10) Uani 1 1 d . . . C9D C -0.1795(5) 0.6477(4) 0.2250(2) 0.0184(10) Uani 1 1 d . . . C10D C -0.3505(6) 0.8370(4) 0.2210(2) 0.0188(10) Uani 1 1 d . . . C11D C 0.0960(6) 0.6489(4) 0.5198(2) 0.0185(10) Uani 1 1 d . . . C12D C -0.0734(6) 0.8354(4) 0.5179(2) 0.0208(10) Uani 1 1 d . . . N9D N -0.1371(5) 0.5718(4) 0.2021(2) 0.0276(10) Uani 1 1 d . . . N10D N -0.4470(5) 0.9095(4) 0.19555(19) 0.0250(9) Uani 1 1 d . . . N11D N 0.1873(5) 0.5729(4) 0.54685(19) 0.0256(10) Uani 1 1 d . . . N12D N -0.1162(6) 0.9060(4) 0.5457(2) 0.0288(10) Uani 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 S1A 0.0229(6) 0.0226(6) 0.0199(6) -0.0076(5) -0.0080(5) 0.0063(5) S2A 0.0215(6) 0.0139(6) 0.0193(6) -0.0054(4) -0.0066(5) 0.0058(5) S3A 0.0217(6) 0.0183(6) 0.0219(6) -0.0089(5) -0.0093(5) 0.0091(5) N1A 0.0143(19) 0.020(2) 0.0188(19) -0.0055(16) -0.0035(16) 0.0001(16) C2A 0.012(2) 0.015(2) 0.019(2) -0.0054(18) -0.0018(18) 0.0010(17) C3A 0.015(2) 0.018(2) 0.020(2) -0.0041(19) -0.0015(18) -0.0013(18) N4A 0.0133(19) 0.020(2) 0.020(2) -0.0007(16) -0.0046(16) -0.0016(16) C5A 0.019(2) 0.024(3) 0.021(2) -0.001(2) -0.0067(19) -0.002(2) C6A 0.024(3) 0.035(3) 0.018(2) -0.001(2) -0.002(2) -0.009(2) C7A 0.027(3) 0.035(3) 0.020(2) -0.007(2) -0.003(2) -0.014(2) C8A 0.023(3) 0.028(3) 0.024(3) -0.009(2) 0.000(2) -0.007(2) C9A 0.014(2) 0.022(3) 0.021(2) -0.0034(19) -0.0023(19) -0.0037(19) C10A 0.014(2) 0.019(2) 0.015(2) -0.0043(18) 0.0031(17) -0.0062(18) C12A 0.019(2) 0.017(2) 0.018(2) -0.0017(19) -0.0064(19) 0.0054(19) C13A 0.019(2) 0.018(2) 0.017(2) -0.0063(19) 0.0011(18) -0.0011(19) C14A 0.016(2) 0.012(2) 0.016(2) -0.0007(17) -0.0028(18) 0.0015(18) C15A 0.015(2) 0.018(2) 0.021(2) -0.0083(19) -0.0062(18) 0.0033(18) S1B 0.0266(7) 0.0220(6) 0.0211(6) -0.0089(5) -0.0115(5) 0.0072(5) S2B 0.0241(6) 0.0130(6) 0.0194(6) -0.0041(4) -0.0083(5) 0.0050(5) S3B 0.0265(6) 0.0150(6) 0.0182(6) -0.0048(4) -0.0086(5) 0.0075(5) N1B 0.0163(19) 0.016(2) 0.0171(19) -0.0020(16) -0.0015(16) 0.0000(16) C2B 0.011(2) 0.020(2) 0.014(2) -0.0047(18) -0.0032(17) -0.0037(18) C3B 0.014(2) 0.018(2) 0.015(2) -0.0035(18) -0.0009(17) 0.0005(18) N4B 0.016(2) 0.021(2) 0.020(2) -0.0049(16) -0.0016(16) 0.0001(16) C5B 0.027(3) 0.026(3) 0.016(2) -0.008(2) 0.001(2) -0.002(2) C6B 0.033(3) 0.030(3) 0.018(2) -0.006(2) -0.001(2) -0.007(2) C7B 0.024(3) 0.033(3) 0.018(2) -0.002(2) -0.007(2) -0.005(2) C8B 0.023(3) 0.019(3) 0.023(3) 0.002(2) -0.005(2) 0.000(2) C9B 0.015(2) 0.024(3) 0.018(2) -0.001(2) -0.0040(18) -0.0019(19) C10B 0.014(2) 0.023(2) 0.015(2) -0.0060(19) -0.0008(18) -0.0021(19) C12B 0.025(3) 0.018(2) 0.022(2) -0.007(2) -0.010(2) 0.003(2) C13B 0.014(2) 0.013(2) 0.020(2) -0.0015(18) 0.0001(18) 0.0027(18) C14B 0.012(2) 0.018(2) 0.017(2) -0.0044(18) -0.0035(17) -0.0014(18) C15B 0.014(2) 0.018(2) 0.017(2) -0.0060(18) -0.0051(18) 0.0026(18) C1C 0.011(2) 0.018(2) 0.016(2) -0.0036(18) -0.0025(17) 0.0059(18) C2C 0.013(2) 0.013(2) 0.023(2) -0.0068(19) -0.0030(18) 0.0051(17) C3C 0.016(2) 0.014(2) 0.020(2) -0.0059(18) -0.0019(18) 0.0062(18) C4C 0.016(2) 0.019(2) 0.019(2) -0.0026(19) 0.0005(18) 0.0009(19) C5C 0.016(2) 0.011(2) 0.018(2) 0.0009(18) -0.0013(18) 0.0037(18) C6C 0.0161(16) 0.0115(16) 0.0175(16) -0.0045(13) -0.0003(13) 0.0040(13) C7C 0.012(2) 0.015(2) 0.019(2) -0.0018(18) -0.0021(18) 0.0016(17) C8C 0.010(2) 0.013(2) 0.018(2) 0.0018(18) -0.0044(17) 0.0032(17) C9C 0.018(2) 0.011(2) 0.018(2) -0.0104(19) 0.0000(19) -0.0003(19) C10C 0.019(2) 0.018(2) 0.018(2) -0.003(2) -0.0090(19) 0.0039(19) C11C 0.014(2) 0.018(2) 0.019(2) -0.0027(19) -0.0012(18) 0.0031(18) C12C 0.019(2) 0.016(2) 0.020(2) -0.007(2) -0.004(2) 0.001(2) N9C 0.023(2) 0.020(2) 0.021(2) -0.0055(17) -0.0028(17) -0.0003(18) N10C 0.022(2) 0.019(2) 0.025(2) -0.0047(18) -0.0099(17) 0.0080(17) N11C 0.024(2) 0.019(2) 0.030(2) -0.0073(19) -0.0053(18) 0.0070(17) N12C 0.030(2) 0.023(2) 0.025(2) -0.0068(19) -0.0052(19) 0.003(2) C1D 0.013(2) 0.013(2) 0.018(2) -0.0014(18) -0.0026(18) 0.0031(17) C2D 0.017(2) 0.012(2) 0.023(2) -0.0075(19) -0.0008(19) 0.0036(18) C3D 0.011(2) 0.014(2) 0.022(2) -0.0022(18) -0.0038(18) 0.0027(17) C4D 0.012(2) 0.017(2) 0.020(2) -0.0026(18) -0.0024(18) -0.0010(18) C5D 0.017(2) 0.012(2) 0.025(2) -0.0065(19) -0.0024(19) 0.0089(18) C6D 0.012(2) 0.014(2) 0.026(2) -0.0060(19) -0.0024(19) 0.0045(18) C7D 0.014(2) 0.013(2) 0.021(2) -0.0022(18) -0.0016(18) 0.0054(18) C8D 0.016(2) 0.016(2) 0.015(2) -0.0032(18) -0.0005(18) 0.0039(18) C9D 0.010(2) 0.018(3) 0.022(2) 0.000(2) -0.0059(18) 0.0070(18) C10D 0.018(2) 0.018(2) 0.020(2) -0.008(2) -0.0017(19) 0.002(2) C11D 0.017(2) 0.019(2) 0.018(2) -0.0047(19) -0.0026(19) 0.004(2) C12D 0.019(2) 0.021(3) 0.019(2) -0.001(2) -0.0079(19) 0.005(2) N9D 0.028(2) 0.026(2) 0.026(2) -0.0062(19) -0.0087(19) 0.0062(19) N10D 0.024(2) 0.021(2) 0.029(2) -0.0099(19) -0.0054(19) 0.0059(19) N11D 0.025(2) 0.024(2) 0.025(2) -0.0036(18) -0.0039(18) 0.0049(19) N12D 0.034(3) 0.027(2) 0.024(2) -0.007(2) -0.0055(19) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A C15A 1.708(5) . ? S1A C12A 1.709(5) . ? S2A C13A 1.750(5) . ? S2A C2A 1.759(5) . ? S3A C14A 1.752(5) . ? S3A C3A 1.756(5) . ? N1A C2A 1.314(6) . ? N1A C9A 1.368(6) . ? C2A C3A 1.443(6) . ? C3A N4A 1.325(6) . ? N4A C10A 1.372(6) . ? C5A C6A 1.379(7) . ? C5A C10A 1.410(7) . ? C6A C7A 1.430(8) . ? C7A C8A 1.350(7) . ? C8A C9A 1.420(7) . ? C9A C10A 1.419(7) . ? C12A C13A 1.382(7) . ? C13A C14A 1.432(6) . ? C14A C15A 1.373(6) . ? S1B C15B 1.696(4) . ? S1B C12B 1.707(5) . ? S2B C13B 1.745(5) . ? S2B C2B 1.759(4) . ? S3B C14B 1.756(5) . ? S3B C3B 1.758(5) . ? N1B C2B 1.323(6) . ? N1B C9B 1.363(6) . ? C2B C3B 1.444(6) . ? C3B N4B 1.323(6) . ? N4B C10B 1.362(6) . ? C5B C6B 1.397(7) . ? C5B C10B 1.418(6) . ? C6B C7B 1.420(8) . ? C7B C8B 1.365(7) . ? C8B C9B 1.406(7) . ? C9B C10B 1.426(7) . ? C12B C13B 1.365(7) . ? C13B C14B 1.451(6) . ? C14B C15B 1.371(6) . ? C1C C7C 1.378(6) . ? C1C C2C 1.450(6) . ? C1C C6C 1.448(6) . ? C2C C3C 1.345(7) . ? C3C C4C 1.450(6) . ? C4C C8C 1.384(7) . ? C4C C5C 1.446(6) . ? C5C C6C 1.344(6) . ? C7C C9C 1.436(6) . ? C7C C10C 1.455(6) . ? C8C C11C 1.431(6) . ? C8C C12C 1.431(6) . ? C9C N9C 1.133(6) . ? C10C N10C 1.123(6) . ? C11C N11C 1.162(6) . ? C12C N12C 1.152(6) . ? C1D C7D 1.376(7) . ? C1D C2D 1.444(6) . ? C1D C6D 1.449(6) . ? C2D C3D 1.343(7) . ? C3D C4D 1.445(6) . ? C4D C8D 1.378(7) . ? C4D C5D 1.453(6) . ? C5D C6D 1.342(7) . ? C7D C10D 1.437(7) . ? C7D C9D 1.448(6) . ? C8D C11D 1.431(6) . ? C8D C12D 1.436(7) . ? C9D N9D 1.138(6) . ? C10D N10D 1.140(6) . ? C11D N11D 1.155(6) . ? C12D N12D 1.156(6) . ? 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 C15A S1A C12A 92.2(2) . . ? C13A S2A C2A 105.1(2) . . ? C14A S3A C3A 104.9(2) . . ? C2A N1A C9A 118.2(4) . . ? N1A C2A C3A 121.6(4) . . ? N1A C2A S2A 112.1(3) . . ? C3A C2A S2A 126.3(3) . . ? N4A C3A C2A 121.1(4) . . ? N4A C3A S3A 111.3(3) . . ? C2A C3A S3A 127.5(4) . . ? C3A N4A C10A 118.0(4) . . ? C6A C5A C10A 119.9(5) . . ? C5A C6A C7A 119.8(5) . . ? C8A C7A C6A 121.3(5) . . ? C7A C8A C9A 119.9(5) . . ? N1A C9A C10A 120.6(4) . . ? N1A C9A C8A 120.0(4) . . ? C10A C9A C8A 119.4(4) . . ? N4A C10A C5A 119.7(4) . . ? N4A C10A C9A 120.5(4) . . ? C5A C10A C9A 119.8(4) . . ? C13A C12A S1A 111.7(3) . . ? C12A C13A C14A 112.1(4) . . ? C12A C13A S2A 120.4(4) . . ? C14A C13A S2A 127.6(4) . . ? C15A C14A C13A 111.9(4) . . ? C15A C14A S3A 121.1(3) . . ? C13A C14A S3A 126.9(4) . . ? C14A C15A S1A 112.1(3) . . ? C15B S1B C12B 92.0(2) . . ? C13B S2B C2B 105.6(2) . . ? C14B S3B C3B 105.5(2) . . ? C2B N1B C9B 118.7(4) . . ? N1B C2B C3B 121.1(4) . . ? N1B C2B S2B 111.9(3) . . ? C3B C2B S2B 126.9(3) . . ? N4B C3B C2B 120.8(4) . . ? N4B C3B S3B 111.8(3) . . ? C2B C3B S3B 127.4(3) . . ? C3B N4B C10B 118.3(4) . . ? C6B C5B C10B 119.1(5) . . ? C5B C6B C7B 119.7(5) . . ? C8B C7B C6B 121.8(5) . . ? C7B C8B C9B 119.7(5) . . ? N1B C9B C8B 120.4(4) . . ? N1B C9B C10B 119.8(4) . . ? C8B C9B C10B 119.8(4) . . ? N4B C10B C5B 119.0(4) . . ? N4B C10B C9B 121.1(4) . . ? C5B C10B C9B 119.9(4) . . ? C13B C12B S1B 112.6(4) . . ? C12B C13B C14B 111.3(4) . . ? C12B C13B S2B 121.1(4) . . ? C14B C13B S2B 127.6(4) . . ? C15B C14B C13B 111.4(4) . . ? C15B C14B S3B 121.7(4) . . ? C13B C14B S3B 126.8(3) . . ? C14B C15B S1B 112.7(3) . . ? C7C C1C C2C 120.5(4) . . ? C7C C1C C6C 122.0(4) . . ? C2C C1C C6C 117.5(4) . . ? C3C C2C C1C 121.1(4) . . ? C2C C3C C4C 120.9(4) . . ? C8C C4C C5C 120.9(4) . . ? C8C C4C C3C 121.0(4) . . ? C5C C4C C3C 118.1(4) . . ? C6C C5C C4C 120.6(4) . . ? C5C C6C C1C 121.6(4) . . ? C1C C7C C9C 123.2(4) . . ? C1C C7C C10C 121.4(4) . . ? C9C C7C C10C 115.5(4) . . ? C4C C8C C11C 121.7(4) . . ? C4C C8C C12C 121.7(4) . . ? C11C C8C C12C 116.6(4) . . ? N9C C9C C7C 178.7(5) . . ? N10C C10C C7C 178.1(5) . . ? N11C C11C C8C 178.0(5) . . ? N12C C12C C8C 178.4(5) . . ? C7D C1D C2D 120.9(4) . . ? C7D C1D C6D 121.4(4) . . ? C2D C1D C6D 117.7(4) . . ? C3D C2D C1D 121.3(4) . . ? C2D C3D C4D 121.1(4) . . ? C8D C4D C3D 120.8(4) . . ? C8D C4D C5D 121.4(4) . . ? C3D C4D C5D 117.8(4) . . ? C6D C5D C4D 120.8(4) . . ? C5D C6D C1D 121.3(4) . . ? C1D C7D C10D 122.2(4) . . ? C1D C7D C9D 121.8(4) . . ? C10D C7D C9D 116.0(4) . . ? C4D C8D C11D 122.2(4) . . ? C4D C8D C12D 122.6(4) . . ? C11D C8D C12D 115.2(4) . . ? N9D C9D C7D 179.6(6) . . ? N10D C10D C7D 178.6(6) . . ? N11D C11D C8D 179.4(5) . . ? N12D C12D C8D 176.6(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.999 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.119 #===================================================END data_16 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,6-bis(methylsulfanyl)[1,4]dithiino[2,3-b]quinoxaline ; _chemical_name_common ? _chemical_melting_point '154-155 deg.C' _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N2 S4' _chemical_formula_weight 310.46 _ccdc_compound_id '16' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; none ; _ccdc_comments '?' 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' '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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 9.5292(19) _cell_length_b 13.975(3) _cell_length_c 10.241(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1363.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5060 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.07 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.678 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6483 _exptl_absorpt_correction_T_max 0.7732 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius FAST TV detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5060 _diffrn_reflns_av_R_equivalents 0.1244 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.07 _reflns_number_total 1121 _reflns_number_gt 939 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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. ; _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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1121 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 0.796 _refine_ls_restrained_S_all 0.796 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.41875(6) 0.63157(4) 0.49526(6) 0.0517(3) Uani 1 1 d . . . S2 S 0.20307(6) 0.63572(5) 0.70089(7) 0.0608(3) Uani 1 1 d . . . N1 N 0.68555(17) 0.64884(12) 0.44677(19) 0.0420(5) Uani 1 1 d . . . C1 C 1.0500(2) 0.70025(18) 0.3657(2) 0.0566(7) Uani 1 1 d . . . H1 H 1.1328 0.6676 0.3477 0.068 Uiso 1 1 calc R . . C2 C 0.9306(2) 0.64972(19) 0.3916(2) 0.0521(6) Uani 1 1 d . . . H2 H 0.9315 0.5832 0.3908 0.062 Uiso 1 1 calc R . . C3 C 0.80581(18) 0.70004(16) 0.4195(2) 0.0398(5) Uani 1 1 d . . . C4 C 0.57321(18) 0.69940(15) 0.47227(19) 0.0361(5) Uani 1 1 d . . . C5 C 0.31949(19) 0.70223(15) 0.6038(2) 0.0407(5) Uani 1 1 d . . . C6 C 0.3149(3) 0.54857(18) 0.7758(3) 0.0626(7) Uani 1 1 d . . . H6A H 0.3478 0.5045 0.7108 0.094 Uiso 1 1 calc R . . H6B H 0.2632 0.5143 0.8414 0.094 Uiso 1 1 calc R . . H6C H 0.3935 0.5801 0.8155 0.094 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 0.0386(4) 0.0496(5) 0.0667(5) -0.0169(3) 0.0139(3) -0.0112(2) S2 0.0379(4) 0.0670(5) 0.0776(6) 0.0145(3) 0.0178(3) -0.0066(2) N1 0.0341(10) 0.0481(10) 0.0437(10) -0.0047(9) 0.0040(7) 0.0022(7) C1 0.0307(11) 0.0937(17) 0.0452(13) -0.0019(12) 0.0028(9) 0.0107(10) C2 0.0383(12) 0.0670(15) 0.0509(14) -0.0036(12) 0.0031(10) 0.0088(10) C3 0.0291(10) 0.0568(12) 0.0334(10) -0.0020(10) 0.0007(8) 0.0009(8) C4 0.0303(10) 0.0454(11) 0.0327(10) -0.0026(9) 0.0029(8) -0.0023(8) C5 0.0285(10) 0.0508(11) 0.0427(12) -0.0010(9) 0.0032(8) -0.0028(8) C6 0.0722(15) 0.0481(13) 0.0673(17) 0.0060(13) 0.0109(13) -0.0047(11) _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 C5 1.762(2) . ? S1 C4 1.7665(19) . ? S2 C5 1.756(2) . ? S2 C6 1.791(3) . ? N1 C4 1.309(3) . ? N1 C3 1.380(3) . ? C1 C2 1.365(3) . ? C1 C1 1.390(5) 7_575 ? C2 C3 1.411(3) . ? C3 C3 1.396(4) 7_575 ? C4 C4 1.414(4) 7_575 ? C5 C5 1.335(4) 7_575 ? 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 C5 S1 C4 103.33(10) . . ? C5 S2 C6 103.11(11) . . ? C4 N1 C3 116.09(18) . . ? C2 C1 C1 121.15(14) . 7_575 ? C1 C2 C3 118.9(2) . . ? N1 C3 C3 121.24(11) . 7_575 ? N1 C3 C2 118.9(2) . . ? C3 C3 C2 119.91(14) 7_575 . ? N1 C4 C4 122.67(12) . 7_575 ? N1 C4 S1 114.73(16) . . ? C4 C4 S1 122.45(7) 7_575 . ? C5 C5 S2 121.96(7) 7_575 . ? C5 C5 S1 124.08(7) 7_575 . ? S2 C5 S1 113.56(12) . . ? _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.885 _refine_diff_density_max 0.288 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.090 #======================================================END