# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Lars Ohrstrom' _publ_contact_author_address ; Department of Chemical and Biological Engineering Chalmers University of Technology Physcial Chemistry Gothenburg 41296 SWEDEN ; _publ_contact_author_email OHRSTROM@CHALMERS.SE _publ_section_title ; Syntheses, crystal structures, optical limiting properties, and DFT calculations of three thiophene-2-aldazine Schiff base derivatives ; loop_ _publ_author_name 'Lars Ohrstrom' 'Anders Eriksson' 'Mohamed Ghazzali' 'Vratislav Langer' 'Cesar Lopes' data_gg _database_code_depnum_ccdc_archive 'CCDC 609791' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2 S2' _chemical_formula_sum 'C10 H8 N2 S2' _chemical_formula_weight 220.30 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6504(7) _cell_length_b 11.4015(8) _cell_length_c 9.6510(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.871(1) _cell_angle_gamma 90.00 _cell_volume 1042.83(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9494 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 33.04 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.469 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8798 _exptl_absorpt_correction_T_max 0.9287 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 18997 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 33.04 _reflns_number_total 3775 _reflns_number_gt 3354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.0730P] 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 3775 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 S1A S 0.24480(4) 0.24294(5) 0.15125(4) 0.03661(10) Uani 1 1 d . . . N1A N 0.04793(12) 0.04354(9) 0.03020(12) 0.0342(3) Uani 1 1 d . . . C1A C -0.01418(13) 0.14156(11) 0.04231(14) 0.0313(3) Uani 1 1 d . . . H1A H -0.1138 0.1466 0.0141 0.033(4) Uiso 1 1 calc R . . C2A C 0.06456(14) 0.24442(12) 0.09810(14) 0.0291(2) Uani 1 1 d . . . C3A C 0.01048(17) 0.35472(11) 0.11093(16) 0.0368(3) Uani 1 1 d . . . H3A H -0.0871 0.3733 0.0866 0.047(5) Uiso 1 1 calc R . . C4A C 0.11694(18) 0.43772(13) 0.16465(16) 0.0407(3) Uani 1 1 d . . . H4A H 0.0987 0.5179 0.1808 0.059(6) Uiso 1 1 calc R . . C5A C 0.24737(17) 0.38934(13) 0.19013(15) 0.0395(3) Uani 1 1 d . . . H5A H 0.3311 0.4320 0.2257 0.062(6) Uiso 1 1 calc R . . S1B S 0.14702(4) 0.23355(3) 0.75606(4) 0.03853(10) Uani 1 1 d . . . N1B N 0.02791(12) 0.04274(10) 0.54938(12) 0.0331(2) Uani 1 1 d . . . C1B C 0.04045(14) 0.14256(12) 0.49040(14) 0.0319(3) Uani 1 1 d . . . H1B H 0.0144 0.1501 0.3909 0.037(4) Uiso 1 1 calc R . . C2B C 0.09394(14) 0.24307(12) 0.57505(14) 0.0294(2) Uani 1 1 d . . . C3B C 0.10608(17) 0.35555(13) 0.52863(18) 0.0390(3) Uani 1 1 d . . . H3B H 0.0811 0.3786 0.4326 0.064(6) Uiso 1 1 calc R . . C4B C 0.16010(17) 0.43364(13) 0.6401(2) 0.0451(3) Uani 1 1 d . . . H4B H 0.1759 0.5148 0.6269 0.088(8) Uiso 1 1 calc R . . C5B C 0.18707(16) 0.37917(13) 0.76901(19) 0.0437(3) Uani 1 1 d . . . H5B H 0.2237 0.4180 0.8553 0.068(7) 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 S1A 0.02738(18) 0.03768(18) 0.0426(2) 0.00060(13) 0.00100(12) -0.00401(12) N1A 0.0300(5) 0.0302(5) 0.0397(6) 0.0045(4) -0.0006(4) -0.0072(4) C1A 0.0273(6) 0.0326(6) 0.0332(6) 0.0049(5) 0.0033(4) -0.0059(4) C2A 0.0263(5) 0.0335(5) 0.0273(6) 0.0027(4) 0.0047(4) -0.0033(4) C3A 0.0365(7) 0.0354(6) 0.0388(7) 0.0001(6) 0.0079(5) -0.0010(5) C4A 0.0537(9) 0.0333(6) 0.0365(7) -0.0034(5) 0.0118(6) -0.0056(6) C5A 0.0441(8) 0.0408(7) 0.0332(7) -0.0029(5) 0.0067(5) -0.0153(6) S1B 0.0447(2) 0.03787(19) 0.0307(2) -0.00241(12) 0.00120(13) 0.00483(13) N1B 0.0346(6) 0.0321(5) 0.0315(5) -0.0049(4) 0.0036(4) 0.0016(4) C1B 0.0299(6) 0.0355(6) 0.0304(6) -0.0021(5) 0.0060(5) 0.0010(5) C2B 0.0253(5) 0.0333(5) 0.0296(6) 0.0007(4) 0.0056(4) 0.0014(4) C3B 0.0399(7) 0.0364(6) 0.0430(8) 0.0048(6) 0.0136(6) -0.0009(5) C4B 0.0404(7) 0.0329(7) 0.0640(10) -0.0041(6) 0.0149(7) -0.0031(6) C5B 0.0379(7) 0.0393(7) 0.0520(9) -0.0151(6) 0.0040(6) 0.0032(6) _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 C5A 1.7099(16) . ? S1A C2A 1.7182(13) . ? N1A C1A 1.2839(18) . ? N1A N1A 1.406(2) 3 ? C1A C2A 1.4451(18) . ? C1A H1A 0.9500 . ? C2A C3A 1.3761(19) . ? C3A C4A 1.421(2) . ? C3A H3A 0.9500 . ? C4A C5A 1.354(2) . ? C4A H4A 0.9500 . ? C5A H5A 0.9500 . ? S1B C5B 1.7039(15) . ? S1B C2B 1.7287(14) . ? N1B C1B 1.2884(18) . ? N1B N1B 1.398(2) 3_556 ? C1B C2B 1.4450(19) . ? C1B H1B 0.9500 . ? C2B C3B 1.371(2) . ? C3B C4B 1.418(2) . ? C3B H3B 0.9500 . ? C4B C5B 1.371(2) . ? C4B H4B 0.9500 . ? C5B H5B 0.9500 . ? 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 C5A S1A C2A 91.60(7) . . ? C1A N1A N1A 111.73(13) . 3 ? N1A C1A C2A 121.24(12) . . ? N1A C1A H1A 119.4 . . ? C2A C1A H1A 119.4 . . ? C3A C2A C1A 126.41(13) . . ? C3A C2A S1A 111.22(10) . . ? C1A C2A S1A 122.33(10) . . ? C2A C3A C4A 112.40(14) . . ? C2A C3A H3A 123.8 . . ? C4A C3A H3A 123.8 . . ? C5A C4A C3A 112.24(13) . . ? C5A C4A H4A 123.9 . . ? C3A C4A H4A 123.9 . . ? C4A C5A S1A 112.54(11) . . ? C4A C5A H5A 123.7 . . ? S1A C5A H5A 123.7 . . ? C5B S1B C2B 91.88(7) . . ? C1B N1B N1B 111.76(14) . 3_556 ? N1B C1B C2B 120.27(13) . . ? N1B C1B H1B 119.9 . . ? C2B C1B H1B 119.9 . . ? C3B C2B C1B 126.92(13) . . ? C3B C2B S1B 111.21(12) . . ? C1B C2B S1B 121.85(10) . . ? C2B C3B C4B 112.42(15) . . ? C2B C3B H3B 123.8 . . ? C4B C3B H3B 123.8 . . ? C5B C4B C3B 112.57(14) . . ? C5B C4B H4B 123.7 . . ? C3B C4B H4B 123.7 . . ? C4B C5B S1B 111.92(12) . . ? C4B C5B H5B 124.0 . . ? S1B C5B H5B 124.0 . . ? 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 N1A N1A C1A C2A -178.20(13) 3 . . . ? N1A C1A C2A C3A 177.34(14) . . . . ? N1A C1A C2A S1A 0.13(19) . . . . ? C5A S1A C2A C3A -0.07(11) . . . . ? C5A S1A C2A C1A 177.52(12) . . . . ? C1A C2A C3A C4A -177.63(13) . . . . ? S1A C2A C3A C4A -0.15(16) . . . . ? C2A C3A C4A C5A 0.37(19) . . . . ? C3A C4A C5A S1A -0.42(17) . . . . ? C2A S1A C5A C4A 0.29(12) . . . . ? N1B N1B C1B C2B 178.87(12) 3_556 . . . ? N1B C1B C2B C3B -176.25(14) . . . . ? N1B C1B C2B S1B 1.65(18) . . . . ? C5B S1B C2B C3B -0.64(12) . . . . ? C5B S1B C2B C1B -178.83(11) . . . . ? C1B C2B C3B C4B 178.78(13) . . . . ? S1B C2B C3B C4B 0.69(17) . . . . ? C2B C3B C4B C5B -0.4(2) . . . . ? C3B C4B C5B S1B -0.10(18) . . . . ? C2B S1B C5B C4B 0.41(12) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.577 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.070 # Attachment 'Ghazzali2.cif' data_m _database_code_depnum_ccdc_archive 'CCDC 609792' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Br2 N2 S2' _chemical_formula_sum 'C10 H6 Br2 N2 S2' _chemical_formula_weight 378.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.5456(2) _cell_length_b 26.9807(13) _cell_length_c 10.0137(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.484(1) _cell_angle_gamma 90.00 _cell_volume 1217.65(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10508 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 33.01 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.92 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 6.971 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0602 _exptl_absorpt_correction_T_max 0.8732 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 21672 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 33.03 _reflns_number_total 4395 _reflns_number_gt 3614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. 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^)+(0.0412P)^2^+0.8675P] 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 4395 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.006 _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 BrA Br -1.25967(5) 1.001930(8) 0.26831(3) 0.03539(7) Uani 1 1 d . . . S1A S -0.90086(12) 0.89636(2) 0.00017(5) 0.02590(10) Uani 1 1 d . . . N1A N -0.4343(3) 0.81965(6) 0.11678(17) 0.0215(3) Uani 1 1 d . . . C1A C -0.5298(4) 0.84853(7) 0.2034(2) 0.0224(4) Uani 1 1 d . . . H1A H -0.4506 0.8454 0.2956 0.031(7) Uiso 1 1 calc R . . C2A C -0.7538(4) 0.88565(8) 0.1653(2) 0.0230(4) Uani 1 1 d . . . C3A C -0.8680(5) 0.91803(8) 0.2511(2) 0.0251(4) Uani 1 1 d . . . H3A H -0.8151 0.9181 0.3461 0.030(7) Uiso 1 1 calc R . . C4A C -1.0744(4) 0.95125(7) 0.1806(2) 0.0256(4) Uani 1 1 d . . . C5A C -1.1164(5) 0.94409(8) 0.0451(2) 0.0279(4) Uani 1 1 d . . . H5A H -1.2477 0.9630 -0.0165 0.035(7) Uiso 1 1 calc R . . BrB Br 0.62747(5) 0.600475(8) 0.08428(2) 0.02794(6) Uani 1 1 d . . . S1B S 0.25230(11) 0.718374(19) 0.30805(5) 0.02234(10) Uani 1 1 d . . . N1B N -0.2129(4) 0.78781(6) 0.17824(17) 0.0218(3) Uani 1 1 d . . . C1B C -0.1267(4) 0.75636(7) 0.09492(19) 0.0202(3) Uani 1 1 d . . . H1B H -0.2119 0.7567 0.0031 0.034(7) Uiso 1 1 calc R . . C2B C 0.0998(4) 0.72050(7) 0.14124(18) 0.0187(3) Uani 1 1 d . . . C3B C 0.2153(4) 0.68437(7) 0.06682(19) 0.0200(3) Uani 1 1 d . . . H3B H 0.1602 0.6795 -0.0271 0.031(7) Uiso 1 1 calc R . . C4B C 0.4276(4) 0.65519(7) 0.14817(19) 0.0198(3) Uani 1 1 d . . . C5B C 0.4718(4) 0.66914(8) 0.27961(19) 0.0227(4) Uani 1 1 d . . . H5B H 0.6072 0.6535 0.3469 0.044(8) 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 BrA 0.03215(12) 0.02322(11) 0.05170(15) -0.00655(9) 0.00882(10) 0.00448(8) S1A 0.0249(2) 0.0249(2) 0.0274(2) -0.00034(18) 0.00152(18) 0.00123(18) N1A 0.0175(7) 0.0205(7) 0.0261(8) 0.0037(6) 0.0018(6) 0.0018(6) C1A 0.0187(8) 0.0218(9) 0.0267(9) 0.0018(7) 0.0027(7) 0.0000(6) C2A 0.0183(8) 0.0223(9) 0.0284(9) 0.0005(7) 0.0029(7) -0.0005(7) C3A 0.0245(9) 0.0205(9) 0.0307(10) -0.0016(7) 0.0053(7) 0.0005(7) C4A 0.0203(8) 0.0180(8) 0.0387(11) -0.0010(8) 0.0047(8) 0.0006(7) C5A 0.0228(9) 0.0228(9) 0.0370(11) 0.0012(8) -0.0004(8) 0.0015(7) BrB 0.02676(11) 0.02027(10) 0.03753(12) 0.00014(8) 0.00695(8) 0.00359(7) S1B 0.0220(2) 0.0265(2) 0.01838(19) -0.00057(17) 0.00191(16) 0.00148(17) N1B 0.0182(7) 0.0225(8) 0.0247(8) 0.0036(6) 0.0025(6) 0.0021(6) C1B 0.0173(7) 0.0217(9) 0.0217(8) 0.0029(7) 0.0027(6) -0.0004(6) C2B 0.0167(7) 0.0202(8) 0.0189(8) 0.0022(6) 0.0016(6) -0.0009(6) C3B 0.0191(8) 0.0210(8) 0.0195(8) 0.0009(6) 0.0011(6) -0.0016(6) C4B 0.0170(7) 0.0190(8) 0.0240(8) 0.0011(6) 0.0040(6) -0.0005(6) C5B 0.0196(8) 0.0244(9) 0.0233(8) 0.0040(7) -0.0005(6) 0.0009(7) _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 BrA C4A 1.882(2) . ? S1A C5A 1.713(2) . ? S1A C2A 1.725(2) . ? N1A C1A 1.283(3) . ? N1A N1B 1.403(2) . ? C1A C2A 1.444(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.374(3) . ? C3A C4A 1.418(3) . ? C3A H3A 0.9500 . ? C4A C5A 1.359(3) . ? C5A H5A 0.9500 . ? BrB C4B 1.8884(19) . ? S1B C5B 1.707(2) . ? S1B C2B 1.7240(19) . ? N1B C1B 1.286(3) . ? C1B C2B 1.445(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.372(3) . ? C3B C4B 1.417(3) . ? C3B H3B 0.9500 . ? C4B C5B 1.358(3) . ? C5B H5B 0.9500 . ? 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 C5A S1A C2A 92.16(11) . . ? C1A N1A N1B 111.23(16) . . ? N1A C1A C2A 122.12(18) . . ? N1A C1A H1A 118.9 . . ? C2A C1A H1A 118.9 . . ? C3A C2A C1A 125.92(19) . . ? C3A C2A S1A 111.22(15) . . ? C1A C2A S1A 122.80(16) . . ? C2A C3A C4A 111.7(2) . . ? C2A C3A H3A 124.1 . . ? C4A C3A H3A 124.1 . . ? C5A C4A C3A 113.88(19) . . ? C5A C4A BrA 123.77(16) . . ? C3A C4A BrA 122.30(17) . . ? C4A C5A S1A 111.00(16) . . ? C4A C5A H5A 124.5 . . ? S1A C5A H5A 124.5 . . ? C5B S1B C2B 91.96(9) . . ? C1B N1B N1A 112.40(16) . . ? N1B C1B C2B 119.87(17) . . ? N1B C1B H1B 120.1 . . ? C2B C1B H1B 120.1 . . ? C3B C2B C1B 127.48(17) . . ? C3B C2B S1B 111.63(14) . . ? C1B C2B S1B 120.87(14) . . ? C2B C3B C4B 111.24(17) . . ? C2B C3B H3B 124.4 . . ? C4B C3B H3B 124.4 . . ? C5B C4B C3B 114.00(17) . . ? C5B C4B BrB 121.86(15) . . ? C3B C4B BrB 124.12(14) . . ? C4B C5B S1B 111.17(14) . . ? C4B C5B H5B 124.4 . . ? S1B C5B H5B 124.4 . . ? 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 N1B N1A C1A C2A 178.56(17) . . . . ? N1A C1A C2A C3A -179.9(2) . . . . ? N1A C1A C2A S1A -2.9(3) . . . . ? C5A S1A C2A C3A -0.12(17) . . . . ? C5A S1A C2A C1A -177.52(18) . . . . ? C1A C2A C3A C4A 177.26(19) . . . . ? S1A C2A C3A C4A 0.0(2) . . . . ? C2A C3A C4A C5A 0.2(3) . . . . ? C2A C3A C4A BrA -177.53(15) . . . . ? C3A C4A C5A S1A -0.3(2) . . . . ? BrA C4A C5A S1A 177.41(11) . . . . ? C2A S1A C5A C4A 0.26(17) . . . . ? C1A N1A N1B C1B 175.88(17) . . . . ? N1A N1B C1B C2B -179.73(16) . . . . ? N1B C1B C2B C3B 179.51(19) . . . . ? N1B C1B C2B S1B 1.3(3) . . . . ? C5B S1B C2B C3B -0.01(15) . . . . ? C5B S1B C2B C1B 178.48(16) . . . . ? C1B C2B C3B C4B -178.14(18) . . . . ? S1B C2B C3B C4B 0.2(2) . . . . ? C2B C3B C4B C5B -0.4(2) . . . . ? C2B C3B C4B BrB 177.97(14) . . . . ? C3B C4B C5B S1B 0.4(2) . . . . ? BrB C4B C5B S1B -178.02(10) . . . . ? C2B S1B C5B C4B -0.21(16) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.347 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.101 # Attachment 'Ghazzali3.cif' data_g _database_code_depnum_ccdc_archive 'CCDC 609793' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Br2 N2 S2' _chemical_formula_sum 'C10 H6 Br2 N2 S2' _chemical_formula_weight 378.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6766(6) _cell_length_b 11.5253(6) _cell_length_c 10.2713(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.797(1) _cell_angle_gamma 90.00 _cell_volume 1255.01(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3510 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 25.37 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 1.10 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 6.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0503 _exptl_absorpt_correction_T_max 0.4974 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_number 10951 _diffrn_reflns_av_R_equivalents 0.0942 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2298 _reflns_number_gt 1584 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+1.0109P] 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 2298 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 BrA Br 0.20096(8) 1.03399(7) -0.11449(7) 0.0412(3) Uani 1 1 d . . . S1A S 0.40495(17) 0.84352(16) -0.06154(16) 0.0301(4) Uani 1 1 d . . . N1A N 0.6030(5) 0.6608(5) 0.0220(6) 0.0338(15) Uani 1 1 d . . . C1A C 0.5723(7) 0.7261(6) 0.1159(7) 0.0312(17) Uani 1 1 d . . . H1A H 0.6146 0.7155 0.2018 0.030(19) Uiso 1 1 calc R . . C2A C 0.4779(6) 0.8125(6) 0.0949(6) 0.0269(16) Uani 1 1 d . . . C3A C 0.4322(6) 0.8819(6) 0.1858(7) 0.0281(16) Uani 1 1 d . . . H3A H 0.4613 0.8788 0.2768 0.04(2) Uiso 1 1 calc R . . C4A C 0.3369(7) 0.9593(6) 0.1312(7) 0.0285(16) Uani 1 1 d . . . H4A H 0.2935 1.0120 0.1811 0.022(17) Uiso 1 1 calc R . . C5A C 0.3154(7) 0.9490(6) 0.0003(7) 0.0299(17) Uani 1 1 d . . . BrB Br 1.09991(7) 0.20590(6) 0.20405(7) 0.0369(3) Uani 1 1 d . . . S1B S 0.91003(18) 0.40830(15) 0.14316(17) 0.0327(5) Uani 1 1 d . . . N1B N 0.6998(5) 0.5820(5) 0.0663(6) 0.0307(14) Uani 1 1 d . . . C1B C 0.7167(7) 0.5065(6) -0.0246(7) 0.0319(17) Uani 1 1 d . . . H1B H 0.6671 0.5114 -0.1075 0.06(3) Uiso 1 1 calc R . . C2B C 0.8101(7) 0.4154(6) -0.0007(6) 0.0270(16) Uani 1 1 d . . . C3B C 0.8277(7) 0.3245(6) -0.0806(7) 0.0354(18) Uani 1 1 d . . . H3B H 0.7818 0.3147 -0.1649 0.028(18) Uiso 1 1 calc R . . C4B C 0.9208(7) 0.2463(6) -0.0263(6) 0.0306(17) Uani 1 1 d . . . H4B H 0.9435 0.1774 -0.0685 0.029(18) Uiso 1 1 calc R . . C5B C 0.9737(6) 0.2810(6) 0.0930(7) 0.0285(16) 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 BrA 0.0392(5) 0.0416(5) 0.0411(5) 0.0061(3) -0.0020(4) 0.0187(4) S1A 0.0314(11) 0.0311(10) 0.0273(9) 0.0017(8) 0.0017(8) 0.0087(8) N1A 0.026(4) 0.032(3) 0.043(4) 0.009(3) 0.001(3) 0.012(3) C1A 0.026(4) 0.032(4) 0.033(4) 0.002(3) -0.009(3) 0.003(3) C2A 0.028(4) 0.022(4) 0.030(4) 0.001(3) 0.001(3) 0.003(3) C3A 0.023(4) 0.028(4) 0.033(4) 0.002(3) 0.000(3) -0.001(3) C4A 0.023(4) 0.024(4) 0.038(4) 0.000(3) 0.003(3) 0.004(3) C5A 0.029(4) 0.024(4) 0.036(4) 0.006(3) 0.000(3) 0.006(3) BrB 0.0307(5) 0.0327(4) 0.0448(5) -0.0064(3) -0.0066(3) 0.0122(3) S1B 0.0346(11) 0.0267(10) 0.0346(10) -0.0067(8) -0.0054(8) 0.0113(9) N1B 0.023(3) 0.032(3) 0.036(3) 0.004(3) -0.002(3) 0.000(3) C1B 0.026(4) 0.038(4) 0.032(4) 0.003(3) 0.002(3) 0.001(3) C2B 0.025(4) 0.027(4) 0.028(4) 0.002(3) 0.002(3) 0.005(3) C3B 0.032(5) 0.043(5) 0.029(4) -0.001(3) -0.004(3) 0.003(4) C4B 0.036(4) 0.030(4) 0.026(4) -0.008(3) 0.005(3) 0.002(3) C5B 0.020(4) 0.029(4) 0.036(4) 0.002(3) 0.003(3) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag BrA C5A 1.871(7) . ? S1A C5A 1.714(7) . ? S1A C2A 1.738(7) . ? N1A C1A 1.295(9) . ? N1A N1B 1.410(8) . ? C1A C2A 1.416(9) . ? C1A H1A 0.9500 . ? C2A C3A 1.363(9) . ? C3A C4A 1.418(9) . ? C3A H3A 0.9500 . ? C4A C5A 1.342(9) . ? C4A H4A 0.9500 . ? BrB C5B 1.871(7) . ? S1B C2B 1.719(7) . ? S1B C5B 1.721(7) . ? N1B C1B 1.304(9) . ? C1B C2B 1.449(10) . ? C1B H1B 0.9500 . ? C2B C3B 1.358(9) . ? C3B C4B 1.407(10) . ? C3B H3B 0.9500 . ? C4B C5B 1.348(9) . ? C4B H4B 0.9500 . ? 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 C5A S1A C2A 90.7(3) . . ? C1A N1A N1B 112.0(6) . . ? N1A C1A C2A 122.2(6) . . ? N1A C1A H1A 118.9 . . ? C2A C1A H1A 118.9 . . ? C3A C2A C1A 127.9(6) . . ? C3A C2A S1A 110.8(5) . . ? C1A C2A S1A 121.3(5) . . ? C2A C3A C4A 113.3(6) . . ? C2A C3A H3A 123.3 . . ? C4A C3A H3A 123.3 . . ? C5A C4A C3A 111.8(6) . . ? C5A C4A H4A 124.1 . . ? C3A C4A H4A 124.1 . . ? C4A C5A S1A 113.4(5) . . ? C4A C5A BrA 127.3(5) . . ? S1A C5A BrA 119.3(4) . . ? C2B S1B C5B 90.6(3) . . ? C1B N1B N1A 110.9(6) . . ? N1B C1B C2B 120.9(7) . . ? N1B C1B H1B 119.6 . . ? C2B C1B H1B 119.6 . . ? C3B C2B C1B 126.8(7) . . ? C3B C2B S1B 111.5(5) . . ? C1B C2B S1B 121.6(5) . . ? C2B C3B C4B 113.3(6) . . ? C2B C3B H3B 123.3 . . ? C4B C3B H3B 123.3 . . ? C5B C4B C3B 111.8(6) . . ? C5B C4B H4B 124.1 . . ? C3B C4B H4B 124.1 . . ? C4B C5B S1B 112.8(5) . . ? C4B C5B BrB 127.6(5) . . ? S1B C5B BrB 119.6(4) . . ? 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 N1B N1A C1A C2A 179.5(6) . . . . ? N1A C1A C2A C3A 176.1(7) . . . . ? N1A C1A C2A S1A -4.7(10) . . . . ? C5A S1A C2A C3A 0.0(5) . . . . ? C5A S1A C2A C1A -179.3(6) . . . . ? C1A C2A C3A C4A -179.7(7) . . . . ? S1A C2A C3A C4A 1.0(8) . . . . ? C2A C3A C4A C5A -1.8(9) . . . . ? C3A C4A C5A S1A 1.9(8) . . . . ? C3A C4A C5A BrA -178.9(5) . . . . ? C2A S1A C5A C4A -1.1(6) . . . . ? C2A S1A C5A BrA 179.6(4) . . . . ? C1A N1A N1B C1B 170.8(6) . . . . ? N1A N1B C1B C2B -178.9(6) . . . . ? N1B C1B C2B C3B 172.3(7) . . . . ? N1B C1B C2B S1B -4.7(10) . . . . ? C5B S1B C2B C3B -0.4(6) . . . . ? C5B S1B C2B C1B 176.9(6) . . . . ? C1B C2B C3B C4B -176.1(7) . . . . ? S1B C2B C3B C4B 1.1(8) . . . . ? C2B C3B C4B C5B -1.3(9) . . . . ? C3B C4B C5B S1B 1.0(8) . . . . ? C3B C4B C5B BrB 179.4(5) . . . . ? C2B S1B C5B C4B -0.3(6) . . . . ? C2B S1B C5B BrB -178.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.714 _refine_diff_density_min -0.806 _refine_diff_density_rms 0.142