data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Fangfang Jian' _publ_contact_author_email FFJ2003@163169.NET _publ_section_title ; Novel quinolonodithiole and 3,5-bis(phenylamino)-1,2-dithiole heterocycles: an effective and facile green route ; loop_ _publ_author_name 'Fangfang Jian.' 'Yufeng Li.' 'Jing Wang.' 'Jian Zheng.' data_1h _database_code_depnum_ccdc_archive 'CCDC 652761' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H13 Cl2 F N2 O S2' _chemical_formula_weight 475.36 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 '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 9.896(2) _cell_length_b 10.256(2) _cell_length_c 11.128(2) _cell_angle_alpha 89.64(3) _cell_angle_beta 73.71(3) _cell_angle_gamma 82.42(3) _cell_volume 1074.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 26.97 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4867 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.97 _reflns_number_total 4592 _reflns_number_gt 3325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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. 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^)+(0.0825P)^2^+0.3312P] 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 4592 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1297 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Cl1 Cl 0.19266(8) 0.84084(9) 0.37425(7) 0.0719(2) Uani 1 1 d . . . Cl2 Cl 0.60094(14) 0.62485(9) 0.57540(11) 0.1107(4) Uani 1 1 d . . . S1 S 0.14609(8) 0.57819(7) 0.01785(7) 0.0615(2) Uani 1 1 d . . . S2 S 0.17082(8) 0.73521(7) -0.10118(7) 0.0580(2) Uani 1 1 d . . . F1 F 0.7655(2) 0.5752(2) 0.3134(3) 0.1121(8) Uani 1 1 d . . . O1 O 0.4772(2) 0.8919(2) 0.07949(19) 0.0678(6) Uani 1 1 d . . . N1 N 0.3321(2) 0.9150(2) -0.08592(18) 0.0487(5) Uani 1 1 d . . . H1A H 0.3961 0.9467 -0.0609 0.058 Uiso 1 1 calc R . . N2 N 0.2916(3) 0.5431(2) 0.1875(2) 0.0578(6) Uani 1 1 d . . . C1 C 0.3568(3) 0.9718(3) -0.3022(2) 0.0577(6) Uani 1 1 d . . . H1B H 0.4447 0.9192 -0.3255 0.069 Uiso 1 1 calc R . . C2 C 0.3041(4) 1.0382(3) -0.3919(3) 0.0681(8) Uani 1 1 d . . . H2B H 0.3566 1.0297 -0.4757 0.082 Uiso 1 1 calc R . . C3 C 0.1753(4) 1.1161(3) -0.3579(3) 0.0690(8) Uani 1 1 d . . . H3A H 0.1400 1.1599 -0.4185 0.083 Uiso 1 1 calc R . . C4 C 0.0989(4) 1.1292(4) -0.2350(4) 0.0824(10) Uani 1 1 d . . . H4A H 0.0111 1.1817 -0.2117 0.099 Uiso 1 1 calc R . . C5 C 0.1517(3) 1.0645(3) -0.1447(3) 0.0709(8) Uani 1 1 d . . . H5A H 0.1007 1.0757 -0.0606 0.085 Uiso 1 1 calc R . . C6 C 0.2790(3) 0.9841(2) -0.1795(2) 0.0464(5) Uani 1 1 d . . . C7 C 0.2876(2) 0.8041(2) -0.0356(2) 0.0429(5) Uani 1 1 d . . . C8 C 0.3268(2) 0.7389(2) 0.0630(2) 0.0426(5) Uani 1 1 d . . . C9 C 0.2664(2) 0.6176(2) 0.1027(2) 0.0431(5) Uani 1 1 d . . . C10 C 0.2178(3) 0.4318(2) 0.2205(2) 0.0501(6) Uani 1 1 d . . . C11 C 0.0854(3) 0.4458(3) 0.3053(3) 0.0682(8) Uani 1 1 d . . . H11A H 0.0413 0.5289 0.3377 0.082 Uiso 1 1 calc R . . C12 C 0.0170(4) 0.3367(3) 0.3429(4) 0.0809(10) Uani 1 1 d . . . H12A H -0.0726 0.3474 0.4004 0.097 Uiso 1 1 calc R . . C13 C 0.0794(4) 0.2137(3) 0.2965(4) 0.0836(11) Uani 1 1 d . . . H13A H 0.0328 0.1409 0.3217 0.100 Uiso 1 1 calc R . . C14 C 0.2118(5) 0.1990(3) 0.2122(4) 0.0873(11) Uani 1 1 d . . . H14A H 0.2550 0.1155 0.1802 0.105 Uiso 1 1 calc R . . C15 C 0.2824(4) 0.3071(3) 0.1739(3) 0.0716(8) Uani 1 1 d . . . H15A H 0.3726 0.2958 0.1174 0.086 Uiso 1 1 calc R . . C16 C 0.4196(3) 0.7943(2) 0.1212(2) 0.0452(5) Uani 1 1 d . . . C17 C 0.4553(2) 0.7369(2) 0.2355(2) 0.0436(5) Uani 1 1 d . . . C18 C 0.3635(3) 0.7602(2) 0.3547(2) 0.0481(5) Uani 1 1 d . . . C19 C 0.4052(3) 0.7237(3) 0.4601(3) 0.0606(7) Uani 1 1 d . . . H19A H 0.3417 0.7397 0.5395 0.073 Uiso 1 1 calc R . . C20 C 0.5419(4) 0.6633(3) 0.4460(3) 0.0675(9) Uani 1 1 d . . . C21 C 0.6320(3) 0.6370(3) 0.3274(4) 0.0715(9) Uani 1 1 d . . . C22 C 0.5913(3) 0.6744(3) 0.2230(3) 0.0602(7) Uani 1 1 d . . . H22A H 0.6551 0.6578 0.1439 0.072 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 Cl1 0.0527(4) 0.0936(6) 0.0662(4) 0.0058(4) -0.0154(3) -0.0013(4) Cl2 0.1797(11) 0.0767(6) 0.1298(8) 0.0410(5) -0.1244(9) -0.0349(6) S1 0.0696(5) 0.0563(4) 0.0778(5) 0.0140(3) -0.0427(4) -0.0293(3) S2 0.0645(4) 0.0628(4) 0.0633(4) 0.0123(3) -0.0383(3) -0.0244(3) F1 0.0903(15) 0.0922(15) 0.172(2) -0.0049(15) -0.0830(16) 0.0248(12) O1 0.0838(14) 0.0734(12) 0.0717(12) 0.0317(10) -0.0465(11) -0.0493(11) N1 0.0526(12) 0.0545(12) 0.0496(11) 0.0130(9) -0.0256(9) -0.0213(9) N2 0.0676(14) 0.0548(13) 0.0659(13) 0.0170(10) -0.0351(11) -0.0269(11) C1 0.0645(16) 0.0551(15) 0.0512(14) 0.0045(11) -0.0165(12) 0.0004(12) C2 0.084(2) 0.0735(19) 0.0478(14) 0.0106(13) -0.0209(14) -0.0109(16) C3 0.083(2) 0.0674(18) 0.0731(19) 0.0209(15) -0.0458(17) -0.0161(16) C4 0.0625(19) 0.092(2) 0.091(2) 0.0095(19) -0.0290(18) 0.0113(17) C5 0.0563(17) 0.092(2) 0.0575(17) 0.0073(15) -0.0104(13) 0.0029(16) C6 0.0501(13) 0.0476(13) 0.0484(13) 0.0095(10) -0.0208(10) -0.0165(10) C7 0.0419(12) 0.0467(12) 0.0435(12) 0.0013(9) -0.0144(9) -0.0121(10) C8 0.0408(12) 0.0470(12) 0.0450(12) 0.0055(9) -0.0166(9) -0.0138(10) C9 0.0407(12) 0.0456(12) 0.0482(12) 0.0004(10) -0.0178(10) -0.0125(10) C10 0.0591(15) 0.0461(13) 0.0561(14) 0.0132(11) -0.0298(12) -0.0171(11) C11 0.0560(16) 0.0476(15) 0.103(2) 0.0151(15) -0.0238(16) -0.0107(12) C12 0.0627(19) 0.071(2) 0.112(3) 0.0335(19) -0.0229(18) -0.0258(16) C13 0.102(3) 0.0567(19) 0.112(3) 0.0340(18) -0.050(2) -0.0397(18) C14 0.126(3) 0.0464(17) 0.094(3) 0.0024(16) -0.035(2) -0.0168(19) C15 0.087(2) 0.0582(17) 0.0655(18) -0.0001(14) -0.0133(16) -0.0155(16) C16 0.0465(13) 0.0468(13) 0.0477(12) 0.0068(10) -0.0185(10) -0.0144(10) C17 0.0481(13) 0.0387(11) 0.0524(13) 0.0047(10) -0.0251(11) -0.0117(10) C18 0.0533(14) 0.0438(12) 0.0551(14) 0.0094(10) -0.0251(11) -0.0143(10) C19 0.083(2) 0.0527(15) 0.0596(16) 0.0146(12) -0.0358(15) -0.0244(14) C20 0.100(2) 0.0435(14) 0.088(2) 0.0212(14) -0.069(2) -0.0224(15) C21 0.0714(19) 0.0448(15) 0.118(3) 0.0050(16) -0.061(2) -0.0010(13) C22 0.0555(16) 0.0553(15) 0.0753(18) -0.0034(13) -0.0300(14) -0.0014(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 Cl1 C18 1.737(3) . ? Cl2 C20 1.725(3) . ? S1 C9 1.798(2) . ? S1 S2 2.0743(11) . ? S2 C7 1.751(2) . ? F1 C21 1.355(3) . ? O1 C16 1.241(3) . ? N1 C7 1.336(3) . ? N1 C6 1.436(3) . ? N1 H1A 0.8600 . ? N2 C9 1.269(3) . ? N2 C10 1.427(3) . ? C1 C6 1.364(4) . ? C1 C2 1.387(4) . ? C1 H1B 0.9300 . ? C2 C3 1.367(5) . ? C2 H2B 0.9300 . ? C3 C4 1.362(5) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 H4A 0.9300 . ? C5 C6 1.369(4) . ? C5 H5A 0.9300 . ? C7 C8 1.401(3) . ? C8 C16 1.435(3) . ? C8 C9 1.463(3) . ? C10 C11 1.374(4) . ? C10 C15 1.385(4) . ? C11 C12 1.385(4) . ? C11 H11A 0.9300 . ? C12 C13 1.365(5) . ? C12 H12A 0.9300 . ? C13 C14 1.371(5) . ? C13 H13A 0.9300 . ? C14 C15 1.389(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.508(3) . ? C17 C22 1.382(4) . ? C17 C18 1.383(4) . ? C18 C19 1.382(3) . ? C19 C20 1.378(4) . ? C19 H19A 0.9300 . ? C20 C21 1.375(5) . ? C21 C22 1.369(4) . ? C22 H22A 0.9300 . ? 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 C9 S1 S2 96.36(8) . . ? C7 S2 S1 95.43(8) . . ? C7 N1 C6 123.73(19) . . ? C7 N1 H1A 118.1 . . ? C6 N1 H1A 118.1 . . ? C9 N2 C10 119.7(2) . . ? C6 C1 C2 119.5(3) . . ? C6 C1 H1B 120.2 . . ? C2 C1 H1B 120.2 . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2B 119.8 . . ? C1 C2 H2B 119.8 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C1 C6 C5 120.2(2) . . ? C1 C6 N1 120.0(2) . . ? C5 C6 N1 119.8(2) . . ? N1 C7 C8 126.0(2) . . ? N1 C7 S2 116.05(17) . . ? C8 C7 S2 117.91(17) . . ? C7 C8 C16 119.4(2) . . ? C7 C8 C9 116.9(2) . . ? C16 C8 C9 123.6(2) . . ? N2 C9 C8 126.4(2) . . ? N2 C9 S1 120.30(18) . . ? C8 C9 S1 113.34(17) . . ? C11 C10 C15 119.1(3) . . ? C11 C10 N2 120.3(2) . . ? C15 C10 N2 120.5(3) . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C13 C14 C15 120.9(3) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 119.5 . . ? C10 C15 C14 119.7(3) . . ? C10 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? O1 C16 C8 122.0(2) . . ? O1 C16 C17 115.6(2) . . ? C8 C16 C17 122.5(2) . . ? C22 C17 C18 118.4(2) . . ? C22 C17 C16 118.8(2) . . ? C18 C17 C16 122.2(2) . . ? C19 C18 C17 121.7(2) . . ? C19 C18 Cl1 118.6(2) . . ? C17 C18 Cl1 119.72(18) . . ? C20 C19 C18 119.1(3) . . ? C20 C19 H19A 120.4 . . ? C18 C19 H19A 120.4 . . ? C21 C20 C19 119.2(3) . . ? C21 C20 Cl2 120.2(3) . . ? C19 C20 Cl2 120.5(3) . . ? F1 C21 C22 119.1(4) . . ? F1 C21 C20 119.3(3) . . ? C22 C21 C20 121.6(3) . . ? C21 C22 C17 119.9(3) . . ? C21 C22 H22A 120.0 . . ? C17 C22 H22A 120.0 . . ? 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 C9 S1 S2 C7 -1.91(11) . . . . ? C6 C1 C2 C3 0.3(5) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C3 C4 C5 C6 -1.9(5) . . . . ? C2 C1 C6 C5 -1.9(4) . . . . ? C2 C1 C6 N1 179.5(3) . . . . ? C4 C5 C6 C1 2.7(5) . . . . ? C4 C5 C6 N1 -178.7(3) . . . . ? C7 N1 C6 C1 -101.6(3) . . . . ? C7 N1 C6 C5 79.8(3) . . . . ? C6 N1 C7 C8 -174.3(2) . . . . ? C6 N1 C7 S2 6.2(3) . . . . ? S1 S2 C7 N1 -179.12(18) . . . . ? S1 S2 C7 C8 1.33(19) . . . . ? N1 C7 C8 C16 2.1(4) . . . . ? S2 C7 C8 C16 -178.43(18) . . . . ? N1 C7 C8 C9 -179.4(2) . . . . ? S2 C7 C8 C9 0.1(3) . . . . ? C10 N2 C9 C8 176.4(2) . . . . ? C10 N2 C9 S1 -3.7(4) . . . . ? C7 C8 C9 N2 178.0(2) . . . . ? C16 C8 C9 N2 -3.5(4) . . . . ? C7 C8 C9 S1 -1.9(3) . . . . ? C16 C8 C9 S1 176.61(19) . . . . ? S2 S1 C9 N2 -177.6(2) . . . . ? S2 S1 C9 C8 2.35(18) . . . . ? C9 N2 C10 C11 -84.3(3) . . . . ? C9 N2 C10 C15 100.0(3) . . . . ? C15 C10 C11 C12 -0.5(5) . . . . ? N2 C10 C11 C12 -176.3(3) . . . . ? C10 C11 C12 C13 -0.1(5) . . . . ? C11 C12 C13 C14 0.3(6) . . . . ? C12 C13 C14 C15 0.0(6) . . . . ? C11 C10 C15 C14 0.9(5) . . . . ? N2 C10 C15 C14 176.7(3) . . . . ? C13 C14 C15 C10 -0.7(6) . . . . ? C7 C8 C16 O1 -6.9(4) . . . . ? C9 C8 C16 O1 174.6(2) . . . . ? C7 C8 C16 C17 174.1(2) . . . . ? C9 C8 C16 C17 -4.4(4) . . . . ? O1 C16 C17 C22 -69.2(3) . . . . ? C8 C16 C17 C22 109.9(3) . . . . ? O1 C16 C17 C18 101.6(3) . . . . ? C8 C16 C17 C18 -79.3(3) . . . . ? C22 C17 C18 C19 0.5(4) . . . . ? C16 C17 C18 C19 -170.3(2) . . . . ? C22 C17 C18 Cl1 178.96(19) . . . . ? C16 C17 C18 Cl1 8.1(3) . . . . ? C17 C18 C19 C20 0.4(4) . . . . ? Cl1 C18 C19 C20 -178.0(2) . . . . ? C18 C19 C20 C21 -2.1(4) . . . . ? C18 C19 C20 Cl2 176.26(19) . . . . ? C19 C20 C21 F1 -178.7(3) . . . . ? Cl2 C20 C21 F1 3.0(4) . . . . ? C19 C20 C21 C22 2.9(4) . . . . ? Cl2 C20 C21 C22 -175.5(2) . . . . ? F1 C21 C22 C17 179.6(2) . . . . ? C20 C21 C22 C17 -1.9(4) . . . . ? C18 C17 C22 C21 0.2(4) . . . . ? C16 C17 C22 C21 171.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.505 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.061 data_1i _database_code_depnum_ccdc_archive 'CCDC 652762' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 Br N2 O S2' _chemical_formula_weight 481.42 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' Br Br -0.2901 2.4595 '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 6.3729(13) _cell_length_b 12.941(3) _cell_length_c 13.413(3) _cell_angle_alpha 108.64(3) _cell_angle_beta 96.27(3) _cell_angle_gamma 96.96(3) _cell_volume 1027.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 2.221 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4243 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3546 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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. 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^)+(0.1908P)^2^+1.1920P] 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 3546 _refine_ls_number_parameters 255 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1315 _refine_ls_R_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.3118 _refine_ls_wR_factor_gt 0.2769 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.044 _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 Br1 Br 0.6087(2) -0.02178(13) 0.85777(11) 0.1280(7) Uani 1 1 d . A . S1 S 0.2979(4) 0.39701(14) 0.89615(15) 0.0663(6) Uani 1 1 d . . . S2 S 0.1294(4) 0.38710(14) 1.01682(15) 0.0618(6) Uani 1 1 d . . . O1 O 0.1259(12) 0.0158(4) 0.9221(5) 0.093(2) Uani 1 1 d . . . N1 N 0.0176(10) 0.2000(5) 1.0485(5) 0.0581(15) Uani 1 1 d . . . H1A H 0.0167 0.1306 1.0363 0.070 Uiso 1 1 calc R . . N2 N 0.3979(12) 0.2161(5) 0.7594(6) 0.078(2) Uani 1 1 d . . . C1 C 0.0010(14) 0.2651(6) 1.2362(7) 0.067(2) Uani 1 1 d . . . H1B H 0.1227 0.2350 1.2482 0.080 Uiso 1 1 calc R . . C2 C -0.1015(18) 0.3196(7) 1.3213(7) 0.080(3) Uani 1 1 d . . . H2B H -0.0485 0.3239 1.3902 0.096 Uiso 1 1 calc R . . C3 C -0.2705(17) 0.3643(7) 1.3050(7) 0.078(2) Uani 1 1 d . . . H3A H -0.3359 0.3998 1.3622 0.094 Uiso 1 1 calc R . . C4 C -0.3516(15) 0.3589(8) 1.2035(9) 0.084(3) Uani 1 1 d . . . H4A H -0.4692 0.3924 1.1927 0.100 Uiso 1 1 calc R . . C5 C -0.2596(12) 0.3047(7) 1.1191(6) 0.0606(18) Uani 1 1 d . . . H5A H -0.3165 0.2996 1.0505 0.073 Uiso 1 1 calc R . . C6 C -0.0839(11) 0.2578(5) 1.1352(5) 0.0491(16) Uani 1 1 d . . . C7 C 0.1128(11) 0.2451(5) 0.9856(5) 0.0500(16) Uani 1 1 d . . . C8 C 0.1960(12) 0.1850(5) 0.8936(6) 0.0531(17) Uani 1 1 d . . . C9 C 0.3025(11) 0.2523(5) 0.8389(6) 0.0508(16) Uani 1 1 d . . . C10 C 0.4903(13) 0.2898(5) 0.7111(6) 0.060(2) Uani 1 1 d . . . C11 C 0.7076(16) 0.3370(7) 0.7453(7) 0.073(2) Uani 1 1 d . . . H11A H 0.7875 0.3229 0.8003 0.088 Uiso 1 1 calc R . . C12 C 0.8017(14) 0.4067(7) 0.6937(7) 0.074(2) Uani 1 1 d . . . H12A H 0.9440 0.4406 0.7162 0.089 Uiso 1 1 calc R . . C13 C 0.6859(16) 0.4238(6) 0.6125(6) 0.068(2) Uani 1 1 d . . . H13A H 0.7494 0.4682 0.5778 0.082 Uiso 1 1 calc R . . C14 C 0.4799(18) 0.3776(7) 0.5809(8) 0.080(3) Uani 1 1 d . . . H14A H 0.4032 0.3912 0.5246 0.095 Uiso 1 1 calc R . . C15 C 0.3770(15) 0.3107(7) 0.6285(8) 0.075(2) Uani 1 1 d . . . H15A H 0.2331 0.2801 0.6052 0.091 Uiso 1 1 calc R . . C16 C 0.1850(13) 0.0678(6) 0.8646(7) 0.065(2) Uani 1 1 d . . . C17 C 0.2270(15) 0.0029(6) 0.7542(8) 0.076(3) Uani 1 1 d . A . C18 C 0.046(2) -0.0153(7) 0.6579(9) 0.118(3) Uani 1 1 d D . . C19 C 0.103(3) -0.0824(9) 0.5650(9) 0.118(3) Uani 1 1 d . A . H19A H 0.0040 -0.0988 0.5034 0.142 Uiso 1 1 calc R . . C20 C 0.284(3) -0.1272(9) 0.5528(11) 0.127(5) Uani 1 1 d . . . H20A H 0.3028 -0.1711 0.4855 0.153 Uiso 1 1 calc R A . C21 C 0.442(2) -0.1081(8) 0.6400(10) 0.105(4) Uani 1 1 d . A . H21A H 0.5693 -0.1361 0.6308 0.126 Uiso 1 1 calc R . . C22 C 0.4073(16) -0.0455(7) 0.7424(8) 0.083(3) Uani 1 1 d . . . C23A C -0.0707(17) 0.0741(9) 0.6837(9) 0.050(3) Uiso 0.80 1 d PD A 1 H23A H -0.1826 0.0634 0.6255 0.076 Uiso 0.80 1 calc PR A 1 H23B H 0.0241 0.1421 0.6964 0.076 Uiso 0.80 1 calc PR A 1 H23C H -0.1322 0.0773 0.7466 0.076 Uiso 0.80 1 calc PR A 1 C23B C -0.119(5) 0.045(3) 0.672(3) 0.043(11) Uiso 0.20 1 d PD A 2 H23D H -0.2162 0.0228 0.6058 0.065 Uiso 0.20 1 calc PR A 2 H23E H -0.0621 0.1220 0.6926 0.065 Uiso 0.20 1 calc PR A 2 H23F H -0.1932 0.0311 0.7258 0.065 Uiso 0.20 1 calc PR A 2 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 Br1 0.0969(10) 0.1451(13) 0.1219(12) 0.0128(9) 0.0203(8) 0.0302(8) S1 0.1051(16) 0.0364(9) 0.0600(11) 0.0173(8) 0.0336(11) -0.0004(9) S2 0.0970(15) 0.0363(9) 0.0555(11) 0.0159(7) 0.0293(10) 0.0070(8) O1 0.144(6) 0.052(3) 0.120(5) 0.050(3) 0.092(5) 0.033(3) N1 0.083(4) 0.041(3) 0.067(4) 0.029(3) 0.038(3) 0.020(3) N2 0.107(5) 0.045(3) 0.098(5) 0.030(3) 0.069(5) 0.008(3) C1 0.081(5) 0.060(4) 0.069(5) 0.031(4) 0.022(4) 0.016(4) C2 0.117(8) 0.068(5) 0.054(5) 0.025(4) 0.014(5) 0.004(5) C3 0.114(7) 0.062(5) 0.071(6) 0.025(4) 0.043(5) 0.030(5) C4 0.078(6) 0.082(6) 0.117(8) 0.051(6) 0.046(6) 0.039(5) C5 0.063(4) 0.071(5) 0.057(4) 0.032(4) 0.016(4) 0.016(4) C6 0.060(4) 0.043(3) 0.051(4) 0.021(3) 0.021(3) 0.008(3) C7 0.060(4) 0.039(3) 0.057(4) 0.019(3) 0.024(3) 0.013(3) C8 0.071(4) 0.036(3) 0.063(4) 0.024(3) 0.033(4) 0.010(3) C9 0.061(4) 0.035(3) 0.062(4) 0.021(3) 0.021(3) 0.003(3) C10 0.079(5) 0.038(3) 0.069(5) 0.020(3) 0.041(4) 0.004(3) C11 0.096(6) 0.070(5) 0.058(5) 0.030(4) 0.021(4) 0.004(5) C12 0.073(5) 0.069(5) 0.074(6) 0.022(4) 0.027(4) -0.016(4) C13 0.102(7) 0.054(4) 0.060(5) 0.026(4) 0.040(5) 0.008(4) C14 0.109(8) 0.070(5) 0.076(6) 0.040(5) 0.027(5) 0.024(5) C15 0.074(5) 0.057(5) 0.097(7) 0.025(4) 0.026(5) 0.009(4) C16 0.074(5) 0.051(4) 0.085(5) 0.029(4) 0.045(4) 0.017(4) C17 0.098(6) 0.031(3) 0.112(7) 0.025(4) 0.069(6) 0.016(4) C18 0.219(10) 0.060(4) 0.071(5) 0.025(3) 0.037(6) -0.012(6) C19 0.219(10) 0.060(4) 0.071(5) 0.025(3) 0.037(6) -0.012(6) C20 0.225(17) 0.065(7) 0.086(8) 0.009(6) 0.055(10) 0.017(9) C21 0.135(9) 0.055(5) 0.111(9) -0.006(5) 0.065(8) 0.017(6) C22 0.097(6) 0.053(5) 0.093(7) 0.013(4) 0.041(5) 0.000(4) _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 Br1 C22 1.817(11) . ? S1 C9 1.788(6) . ? S1 S2 2.066(3) . ? S2 C7 1.736(6) . ? O1 C16 1.234(9) . ? N1 C7 1.327(9) . ? N1 C6 1.433(9) . ? N1 H1A 0.8600 . ? N2 C9 1.271(10) . ? N2 C10 1.421(9) . ? C1 C6 1.373(10) . ? C1 C2 1.409(13) . ? C1 H1B 0.9300 . ? C2 C3 1.312(13) . ? C2 H2B 0.9300 . ? C3 C4 1.379(13) . ? C3 H3A 0.9300 . ? C4 C5 1.362(12) . ? C4 H4A 0.9300 . ? C5 C6 1.365(10) . ? C5 H5A 0.9300 . ? C7 C8 1.428(9) . ? C8 C16 1.431(9) . ? C8 C9 1.461(9) . ? C10 C15 1.373(12) . ? C10 C11 1.407(12) . ? C11 C12 1.418(11) . ? C11 H11A 0.9300 . ? C12 C13 1.341(12) . ? C12 H12A 0.9300 . ? C13 C14 1.336(13) . ? C13 H13A 0.9300 . ? C14 C15 1.377(12) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.521(11) . ? C17 C22 1.374(13) . ? C17 C18 1.572(15) . ? C18 C23B 1.373(10) . ? C18 C19 1.386(16) . ? C18 C23A 1.421(9) . ? C19 C20 1.36(2) . ? C19 H19A 0.9300 . ? C20 C21 1.394(19) . ? C20 H20A 0.9300 . ? C21 C22 1.411(13) . ? C21 H21A 0.9300 . ? C23A H23A 0.9600 . ? C23A H23B 0.9600 . ? C23A H23C 0.9600 . ? C23B H23D 0.9600 . ? C23B H23E 0.9600 . ? C23B H23F 0.9600 . ? 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 C9 S1 S2 96.8(2) . . ? C7 S2 S1 95.3(2) . . ? C7 N1 C6 125.3(5) . . ? C7 N1 H1A 117.4 . . ? C6 N1 H1A 117.4 . . ? C9 N2 C10 120.0(6) . . ? C6 C1 C2 118.1(8) . . ? C6 C1 H1B 120.9 . . ? C2 C1 H1B 120.9 . . ? C3 C2 C1 121.1(8) . . ? C3 C2 H2B 119.4 . . ? C1 C2 H2B 119.4 . . ? C2 C3 C4 120.4(8) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 120.0(8) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C5 C6 120.1(8) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C5 C6 C1 120.3(7) . . ? C5 C6 N1 121.7(6) . . ? C1 C6 N1 118.0(7) . . ? N1 C7 C8 124.7(6) . . ? N1 C7 S2 116.8(5) . . ? C8 C7 S2 118.4(5) . . ? C7 C8 C16 120.4(6) . . ? C7 C8 C9 115.3(6) . . ? C16 C8 C9 124.2(6) . . ? N2 C9 C8 125.4(6) . . ? N2 C9 S1 120.6(5) . . ? C8 C9 S1 114.0(5) . . ? C15 C10 C11 119.6(7) . . ? C15 C10 N2 121.8(8) . . ? C11 C10 N2 118.5(8) . . ? C10 C11 C12 118.3(8) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? C13 C12 C11 120.1(8) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 120.5(7) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 122.5(9) . . ? C13 C14 H14A 118.7 . . ? C15 C14 H14A 118.7 . . ? C10 C15 C14 118.9(9) . . ? C10 C15 H15A 120.6 . . ? C14 C15 H15A 120.6 . . ? O1 C16 C8 122.6(7) . . ? O1 C16 C17 118.3(6) . . ? C8 C16 C17 118.9(6) . . ? C22 C17 C16 120.4(9) . . ? C22 C17 C18 122.4(8) . . ? C16 C17 C18 117.0(7) . . ? C23B C18 C19 130(2) . . ? C23B C18 C23A 17.7(18) . . ? C19 C18 C23A 134.9(11) . . ? C23B C18 C17 120.0(19) . . ? C19 C18 C17 109.5(11) . . ? C23A C18 C17 108.8(8) . . ? C20 C19 C18 128.0(13) . . ? C20 C19 H19A 116.0 . . ? C18 C19 H19A 116.0 . . ? C19 C20 C21 120.8(11) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C20 C21 C22 119.0(12) . . ? C20 C21 H21A 120.5 . . ? C22 C21 H21A 120.5 . . ? C17 C22 C21 120.1(11) . . ? C17 C22 Br1 119.9(7) . . ? C21 C22 Br1 119.9(9) . . ? C18 C23A H23A 109.5 . . ? C18 C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C18 C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C18 C23B H23D 109.5 . . ? C18 C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C18 C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? 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 C9 S1 S2 C7 2.1(4) . . . . ? C6 C1 C2 C3 -1.5(13) . . . . ? C1 C2 C3 C4 -0.1(14) . . . . ? C2 C3 C4 C5 1.6(15) . . . . ? C3 C4 C5 C6 -1.5(13) . . . . ? C4 C5 C6 C1 -0.1(12) . . . . ? C4 C5 C6 N1 -180.0(7) . . . . ? C2 C1 C6 C5 1.6(11) . . . . ? C2 C1 C6 N1 -178.5(7) . . . . ? C7 N1 C6 C5 63.8(10) . . . . ? C7 N1 C6 C1 -116.1(8) . . . . ? C6 N1 C7 C8 -173.9(7) . . . . ? C6 N1 C7 S2 4.3(10) . . . . ? S1 S2 C7 N1 177.8(6) . . . . ? S1 S2 C7 C8 -3.9(6) . . . . ? N1 C7 C8 C16 -1.5(12) . . . . ? S2 C7 C8 C16 -179.7(6) . . . . ? N1 C7 C8 C9 -177.5(7) . . . . ? S2 C7 C8 C9 4.3(10) . . . . ? C10 N2 C9 C8 178.2(7) . . . . ? C10 N2 C9 S1 -4.0(12) . . . . ? C7 C8 C9 N2 175.8(8) . . . . ? C16 C8 C9 N2 0.0(14) . . . . ? C7 C8 C9 S1 -2.2(9) . . . . ? C16 C8 C9 S1 -177.9(7) . . . . ? S2 S1 C9 N2 -178.4(7) . . . . ? S2 S1 C9 C8 -0.4(6) . . . . ? C9 N2 C10 C15 -90.4(11) . . . . ? C9 N2 C10 C11 93.4(10) . . . . ? C15 C10 C11 C12 1.0(12) . . . . ? N2 C10 C11 C12 177.3(7) . . . . ? C10 C11 C12 C13 -1.8(13) . . . . ? C11 C12 C13 C14 1.5(13) . . . . ? C12 C13 C14 C15 -0.3(14) . . . . ? C11 C10 C15 C14 0.1(12) . . . . ? N2 C10 C15 C14 -176.0(8) . . . . ? C13 C14 C15 C10 -0.5(13) . . . . ? C7 C8 C16 O1 -7.8(13) . . . . ? C9 C8 C16 O1 167.7(8) . . . . ? C7 C8 C16 C17 166.1(8) . . . . ? C9 C8 C16 C17 -18.3(12) . . . . ? O1 C16 C17 C22 -74.0(11) . . . . ? C8 C16 C17 C22 111.7(9) . . . . ? O1 C16 C17 C18 100.1(9) . . . . ? C8 C16 C17 C18 -74.2(9) . . . . ? C22 C17 C18 C23B -173(2) . . . . ? C16 C17 C18 C23B 13(2) . . . . ? C22 C17 C18 C19 -1.6(12) . . . . ? C16 C17 C18 C19 -175.6(7) . . . . ? C22 C17 C18 C23A -157.4(9) . . . . ? C16 C17 C18 C23A 28.6(11) . . . . ? C23B C18 C19 C20 169(3) . . . . ? C23A C18 C19 C20 146.1(16) . . . . ? C17 C18 C19 C20 -0.7(15) . . . . ? C18 C19 C20 C21 0(2) . . . . ? C19 C20 C21 C22 3.0(18) . . . . ? C16 C17 C22 C21 178.3(8) . . . . ? C18 C17 C22 C21 4.6(12) . . . . ? C16 C17 C22 Br1 -5.6(10) . . . . ? C18 C17 C22 Br1 -179.3(6) . . . . ? C20 C21 C22 C17 -5.2(15) . . . . ? C20 C21 C22 Br1 178.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.172 _refine_diff_density_min -1.035 _refine_diff_density_rms 0.132 data_2e _database_code_depnum_ccdc_archive 'CCDC 652763' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H13 Cl N2 O S2' _chemical_formula_weight 420.91 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.497(2) _cell_length_b 7.5370(15) _cell_length_c 22.384(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.64(3) _cell_angle_gamma 90.00 _cell_volume 1884.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 26.96 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.440 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4160 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.96 _reflns_number_total 3966 _reflns_number_gt 2283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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. 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^)+(0.0999P)^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 3966 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Cl1 Cl 1.04276(8) 0.42210(14) 0.11606(4) 0.0631(3) Uani 1 1 d . . . S1 S 0.23643(8) 0.22627(14) 0.01827(4) 0.0563(3) Uani 1 1 d . . . S2 S 0.36716(8) 0.29103(14) 0.09537(4) 0.0550(3) Uani 1 1 d . . . O1 O 0.5439(2) 0.1769(4) -0.08889(10) 0.0684(8) Uani 1 1 d . . . N1 N 0.5958(2) 0.3070(4) 0.09315(10) 0.0444(7) Uani 1 1 d . . . N2 N 0.2948(3) 0.1876(4) -0.09283(12) 0.0526(7) Uani 1 1 d . . . C1 C 0.6377(3) 0.1593(6) 0.19236(16) 0.0648(11) Uani 1 1 d . . . H1A H 0.6457 0.0528 0.1728 0.078 Uiso 1 1 calc R . . C2 C 0.6499(4) 0.1677(8) 0.25567(19) 0.0902(16) Uani 1 1 d . . . H2B H 0.6683 0.0657 0.2794 0.108 Uiso 1 1 calc R . . C3 C 0.6348(4) 0.3280(10) 0.28341(18) 0.101(2) Uani 1 1 d . . . H3A H 0.6403 0.3312 0.3255 0.121 Uiso 1 1 calc R . . C4 C 0.6118(4) 0.4829(8) 0.24971(19) 0.0898(17) Uani 1 1 d . . . H4A H 0.6044 0.5896 0.2694 0.108 Uiso 1 1 calc R . . C5 C 0.5997(3) 0.4795(6) 0.18670(15) 0.0650(11) Uani 1 1 d . . . H5A H 0.5833 0.5824 0.1633 0.078 Uiso 1 1 calc R . . C6 C 0.6130(3) 0.3174(5) 0.15960(13) 0.0476(8) Uani 1 1 d . . . C7 C 0.4841(3) 0.2764(4) 0.05806(14) 0.0441(8) Uani 1 1 d . . . C8 C 0.4581(3) 0.2381(4) -0.00413(14) 0.0444(8) Uani 1 1 d . . . C9 C 0.3330(3) 0.2114(4) -0.03503(14) 0.0466(8) Uani 1 1 d . . . C10 C 0.1743(3) 0.1665(5) -0.12466(15) 0.0504(8) Uani 1 1 d . . . C11 C 0.0847(3) 0.0851(5) -0.10169(17) 0.0599(10) Uani 1 1 d . . . H11A H 0.1021 0.0434 -0.0614 0.072 Uiso 1 1 calc R . . C12 C -0.0289(4) 0.0660(6) -0.1381(2) 0.0717(11) Uani 1 1 d . . . H12A H -0.0877 0.0113 -0.1223 0.086 Uiso 1 1 calc R . . C13 C -0.0564(4) 0.1269(6) -0.1976(2) 0.0719(12) Uani 1 1 d . . . H13A H -0.1338 0.1148 -0.2218 0.086 Uiso 1 1 calc R . . C14 C 0.0303(4) 0.2057(6) -0.22132(19) 0.0694(11) Uani 1 1 d . . . H14A H 0.0116 0.2473 -0.2616 0.083 Uiso 1 1 calc R . . C15 C 0.1456(4) 0.2235(5) -0.18564(17) 0.0638(10) Uani 1 1 d . . . H15A H 0.2045 0.2739 -0.2025 0.077 Uiso 1 1 calc R . . C16 C 0.5568(3) 0.2242(5) -0.03489(14) 0.0475(8) Uani 1 1 d . . . C17 C 0.6766(3) 0.2709(4) 0.00321(13) 0.0440(8) Uani 1 1 d . . . C18 C 0.6937(3) 0.3124(4) 0.06627(13) 0.0425(8) Uani 1 1 d . . . C19 C 0.8078(3) 0.3570(5) 0.10077(14) 0.0469(8) Uani 1 1 d . . . H19A H 0.8198 0.3830 0.1424 0.056 Uiso 1 1 calc R . . C20 C 0.9020(3) 0.3621(4) 0.07288(14) 0.0471(8) Uani 1 1 d . . . C21 C 0.8874(3) 0.3197(5) 0.01089(15) 0.0498(8) Uani 1 1 d . . . H21A H 0.9524 0.3209 -0.0072 0.060 Uiso 1 1 calc R . . C22 C 0.7754(3) 0.2763(5) -0.02269(14) 0.0492(8) Uani 1 1 d . . . H22A H 0.7650 0.2495 -0.0642 0.059 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 Cl1 0.0541(5) 0.0820(7) 0.0554(5) -0.0029(5) 0.0174(4) -0.0076(5) S1 0.0508(5) 0.0707(7) 0.0508(5) -0.0062(4) 0.0188(4) 0.0008(4) S2 0.0522(5) 0.0760(7) 0.0421(5) -0.0053(4) 0.0216(4) 0.0018(5) O1 0.0656(16) 0.108(2) 0.0356(13) -0.0115(13) 0.0197(11) -0.0032(15) N1 0.0488(16) 0.0561(18) 0.0310(13) -0.0005(12) 0.0149(11) 0.0013(13) N2 0.0548(17) 0.0585(19) 0.0447(15) -0.0018(14) 0.0120(13) -0.0001(14) C1 0.062(2) 0.085(3) 0.049(2) 0.014(2) 0.0160(18) -0.009(2) C2 0.075(3) 0.144(5) 0.049(2) 0.036(3) 0.010(2) -0.027(3) C3 0.054(2) 0.220(7) 0.031(2) -0.002(3) 0.0145(18) -0.021(3) C4 0.058(2) 0.163(5) 0.049(2) -0.038(3) 0.0144(19) 0.010(3) C5 0.060(2) 0.092(3) 0.0437(19) -0.015(2) 0.0131(16) 0.013(2) C6 0.0440(17) 0.071(2) 0.0311(15) -0.0006(16) 0.0150(13) 0.0021(16) C7 0.0514(19) 0.047(2) 0.0381(16) 0.0026(14) 0.0195(14) 0.0064(15) C8 0.0516(18) 0.047(2) 0.0380(16) 0.0011(14) 0.0166(14) 0.0015(15) C9 0.0538(19) 0.046(2) 0.0443(18) 0.0019(15) 0.0200(15) 0.0020(16) C10 0.054(2) 0.049(2) 0.0478(19) -0.0092(16) 0.0123(16) 0.0018(16) C11 0.070(2) 0.053(2) 0.059(2) -0.0019(18) 0.0204(19) -0.0082(19) C12 0.060(2) 0.068(3) 0.088(3) -0.014(2) 0.021(2) -0.010(2) C13 0.055(2) 0.073(3) 0.081(3) -0.020(2) 0.003(2) 0.004(2) C14 0.070(3) 0.074(3) 0.056(2) -0.004(2) -0.0007(19) -0.006(2) C15 0.065(2) 0.073(3) 0.053(2) -0.0028(19) 0.0113(18) -0.006(2) C16 0.056(2) 0.055(2) 0.0333(16) 0.0031(15) 0.0140(14) 0.0051(16) C17 0.0549(19) 0.046(2) 0.0348(15) 0.0034(14) 0.0179(14) 0.0041(15) C18 0.0527(19) 0.0414(19) 0.0391(16) 0.0038(14) 0.0222(14) 0.0077(15) C19 0.055(2) 0.054(2) 0.0344(16) -0.0003(14) 0.0145(14) 0.0024(16) C20 0.0517(19) 0.045(2) 0.0478(18) 0.0027(15) 0.0182(15) 0.0030(15) C21 0.058(2) 0.055(2) 0.0454(18) 0.0040(16) 0.0287(16) 0.0033(17) C22 0.063(2) 0.055(2) 0.0346(16) -0.0007(15) 0.0219(15) 0.0040(17) _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 Cl1 C20 1.737(3) . ? S1 C9 1.815(3) . ? S1 S2 2.0620(15) . ? S2 C7 1.745(3) . ? O1 C16 1.235(4) . ? N1 C7 1.358(4) . ? N1 C18 1.397(4) . ? N1 C6 1.456(3) . ? N2 C9 1.277(4) . ? N2 C10 1.409(4) . ? C1 C2 1.392(5) . ? C1 C6 1.393(5) . ? C1 H1A 0.9300 . ? C2 C3 1.388(8) . ? C2 H2B 0.9300 . ? C3 C4 1.382(7) . ? C3 H3A 0.9300 . ? C4 C5 1.385(5) . ? C4 H4A 0.9300 . ? C5 C6 1.389(5) . ? C5 H5A 0.9300 . ? C7 C8 1.384(4) . ? C8 C9 1.455(5) . ? C8 C16 1.464(4) . ? C10 C15 1.394(5) . ? C10 C11 1.397(5) . ? C11 C12 1.374(5) . ? C11 H11A 0.9300 . ? C12 C13 1.374(6) . ? C12 H12A 0.9300 . ? C13 C14 1.370(6) . ? C13 H13A 0.9300 . ? C14 C15 1.383(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.481(5) . ? C17 C22 1.393(4) . ? C17 C18 1.413(4) . ? C18 C19 1.397(5) . ? C19 C20 1.373(4) . ? C19 H19A 0.9300 . ? C20 C21 1.395(4) . ? C21 C22 1.369(5) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? 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 C9 S1 S2 97.28(12) . . ? C7 S2 S1 94.38(11) . . ? C7 N1 C18 120.3(2) . . ? C7 N1 C6 118.8(2) . . ? C18 N1 C6 120.6(3) . . ? C9 N2 C10 126.2(3) . . ? C2 C1 C6 117.2(4) . . ? C2 C1 H1A 121.4 . . ? C6 C1 H1A 121.4 . . ? C3 C2 C1 120.1(5) . . ? C3 C2 H2B 119.9 . . ? C1 C2 H2B 119.9 . . ? C4 C3 C2 121.3(4) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C5 C6 117.8(4) . . ? C4 C5 H5A 121.1 . . ? C6 C5 H5A 121.1 . . ? C5 C6 C1 123.5(3) . . ? C5 C6 N1 119.4(3) . . ? C1 C6 N1 117.0(3) . . ? N1 C7 C8 124.6(3) . . ? N1 C7 S2 116.3(2) . . ? C8 C7 S2 119.1(3) . . ? C7 C8 C9 117.5(3) . . ? C7 C8 C16 118.7(3) . . ? C9 C8 C16 123.8(3) . . ? N2 C9 C8 124.5(3) . . ? N2 C9 S1 123.8(3) . . ? C8 C9 S1 111.6(2) . . ? C15 C10 C11 118.1(3) . . ? C15 C10 N2 116.0(3) . . ? C11 C10 N2 125.8(3) . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C14 C13 C12 119.8(4) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C15 120.3(4) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C14 C15 C10 120.6(4) . . ? C14 C15 H15A 119.7 . . ? C10 C15 H15A 119.7 . . ? O1 C16 C8 123.6(3) . . ? O1 C16 C17 120.9(3) . . ? C8 C16 C17 115.5(3) . . ? C22 C17 C18 118.3(3) . . ? C22 C17 C16 120.4(3) . . ? C18 C17 C16 121.3(3) . . ? C19 C18 N1 121.1(3) . . ? C19 C18 C17 119.8(3) . . ? N1 C18 C17 119.1(3) . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C19 C20 C21 121.6(3) . . ? C19 C20 Cl1 119.1(3) . . ? C21 C20 Cl1 119.4(3) . . ? C22 C21 C20 118.5(3) . . ? C22 C21 H21A 120.7 . . ? C20 C21 H21A 120.7 . . ? C21 C22 C17 122.2(3) . . ? C21 C22 H22A 118.9 . . ? C17 C22 H22A 118.9 . . ? 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 C9 S1 S2 C7 -2.92(16) . . . . ? C6 C1 C2 C3 1.5(6) . . . . ? C1 C2 C3 C4 -2.3(7) . . . . ? C2 C3 C4 C5 2.0(7) . . . . ? C3 C4 C5 C6 -0.8(6) . . . . ? C4 C5 C6 C1 0.0(6) . . . . ? C4 C5 C6 N1 177.3(3) . . . . ? C2 C1 C6 C5 -0.3(5) . . . . ? C2 C1 C6 N1 -177.7(3) . . . . ? C7 N1 C6 C5 -88.4(4) . . . . ? C18 N1 C6 C5 97.3(4) . . . . ? C7 N1 C6 C1 89.1(4) . . . . ? C18 N1 C6 C1 -85.2(4) . . . . ? C18 N1 C7 C8 4.2(5) . . . . ? C6 N1 C7 C8 -170.2(3) . . . . ? C18 N1 C7 S2 -174.8(2) . . . . ? C6 N1 C7 S2 10.9(4) . . . . ? S1 S2 C7 N1 -178.7(2) . . . . ? S1 S2 C7 C8 2.2(3) . . . . ? N1 C7 C8 C9 -179.1(3) . . . . ? S2 C7 C8 C9 -0.1(4) . . . . ? N1 C7 C8 C16 1.7(5) . . . . ? S2 C7 C8 C16 -179.3(2) . . . . ? C10 N2 C9 C8 -178.0(3) . . . . ? C10 N2 C9 S1 -1.0(5) . . . . ? C7 C8 C9 N2 174.9(3) . . . . ? C16 C8 C9 N2 -6.0(5) . . . . ? C7 C8 C9 S1 -2.5(4) . . . . ? C16 C8 C9 S1 176.6(3) . . . . ? S2 S1 C9 N2 -174.0(3) . . . . ? S2 S1 C9 C8 3.4(2) . . . . ? C9 N2 C10 C15 151.1(4) . . . . ? C9 N2 C10 C11 -32.9(6) . . . . ? C15 C10 C11 C12 -1.5(5) . . . . ? N2 C10 C11 C12 -177.4(3) . . . . ? C10 C11 C12 C13 -0.1(6) . . . . ? C11 C12 C13 C14 0.8(6) . . . . ? C12 C13 C14 C15 0.2(6) . . . . ? C13 C14 C15 C10 -1.9(6) . . . . ? C11 C10 C15 C14 2.5(6) . . . . ? N2 C10 C15 C14 178.8(3) . . . . ? C7 C8 C16 O1 174.1(3) . . . . ? C9 C8 C16 O1 -5.1(5) . . . . ? C7 C8 C16 C17 -5.8(5) . . . . ? C9 C8 C16 C17 175.0(3) . . . . ? O1 C16 C17 C22 5.3(5) . . . . ? C8 C16 C17 C22 -174.8(3) . . . . ? O1 C16 C17 C18 -175.3(3) . . . . ? C8 C16 C17 C18 4.7(5) . . . . ? C7 N1 C18 C19 175.1(3) . . . . ? C6 N1 C18 C19 -10.7(5) . . . . ? C7 N1 C18 C17 -5.3(5) . . . . ? C6 N1 C18 C17 168.9(3) . . . . ? C22 C17 C18 C19 -0.2(5) . . . . ? C16 C17 C18 C19 -179.6(3) . . . . ? C22 C17 C18 N1 -179.7(3) . . . . ? C16 C17 C18 N1 0.8(5) . . . . ? N1 C18 C19 C20 -179.6(3) . . . . ? C17 C18 C19 C20 0.8(5) . . . . ? C18 C19 C20 C21 -1.5(5) . . . . ? C18 C19 C20 Cl1 178.7(2) . . . . ? C19 C20 C21 C22 1.6(5) . . . . ? Cl1 C20 C21 C22 -178.7(3) . . . . ? C20 C21 C22 C17 -0.9(5) . . . . ? C18 C17 C22 C21 0.2(5) . . . . ? C16 C17 C22 C21 179.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.603 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.079 # Attachment 'cif.cif' data_1e _database_code_depnum_ccdc_archive 'CCDC 652764' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 Cl2 N2 O S2' _chemical_formula_weight 457.37 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' Cl Cl 0.1484 0.1585 '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 10.084(2) _cell_length_b 10.331(2) _cell_length_c 10.414(2) _cell_angle_alpha 87.60(3) _cell_angle_beta 85.58(3) _cell_angle_gamma 78.10(3) _cell_volume 1058.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 26.97 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.520 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4872 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0939 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.97 _reflns_number_total 4604 _reflns_number_gt 2192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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. 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^)+(0.1044P)^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 SHELXL _refine_ls_extinction_coef 0.007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4604 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1616 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.2053 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 Cl1 Cl -0.30253(16) 0.1448(2) 0.95117(15) 0.0904(6) Uani 1 1 d . . . Cl2 Cl 0.28010(14) 0.10702(15) 0.69545(15) 0.0716(5) Uani 1 1 d . . . S1 S 0.34108(15) 0.47932(15) 0.93360(13) 0.0667(5) Uani 1 1 d . . . S2 S 0.33233(14) 0.59898(14) 0.76873(13) 0.0625(5) Uani 1 1 d . . . O1 O 0.0151(3) 0.4067(4) 0.6122(3) 0.0620(10) Uani 1 1 d . . . N1 N 0.1741(4) 0.5798(4) 0.5868(3) 0.0511(10) Uani 1 1 d . . . H1A H 0.1084 0.5537 0.5545 0.061 Uiso 1 1 calc R . . N2 N 0.1750(4) 0.3085(4) 0.9763(3) 0.0487(10) Uani 1 1 d . . . C1 C 0.1723(7) 0.8063(6) 0.5168(5) 0.0723(17) Uani 1 1 d . . . H1B H 0.0896 0.8337 0.5636 0.087 Uiso 1 1 calc R . . C2 C 0.2373(8) 0.8981(6) 0.4451(6) 0.085(2) Uani 1 1 d . . . H2B H 0.1976 0.9877 0.4458 0.102 Uiso 1 1 calc R . . C3 C 0.3567(8) 0.8566(8) 0.3755(6) 0.090(2) Uani 1 1 d . . . H3A H 0.3988 0.9180 0.3297 0.108 Uiso 1 1 calc R . . C4 C 0.4144(7) 0.7280(8) 0.3724(6) 0.087(2) Uani 1 1 d . . . H4A H 0.4954 0.7007 0.3228 0.105 Uiso 1 1 calc R . . C5 C 0.3551(6) 0.6346(6) 0.4420(6) 0.0713(16) Uani 1 1 d . . . H5A H 0.3957 0.5453 0.4394 0.086 Uiso 1 1 calc R . . C6 C 0.2358(5) 0.6762(5) 0.5146(4) 0.0466(12) Uani 1 1 d . . . C7 C 0.2121(4) 0.5286(5) 0.7000(4) 0.0438(11) Uani 1 1 d . . . C8 C 0.1633(4) 0.4270(4) 0.7693(4) 0.0378(10) Uani 1 1 d . . . C9 C 0.2128(4) 0.3914(4) 0.8953(4) 0.0403(10) Uani 1 1 d . . . C10 C 0.2389(5) 0.2802(4) 1.0937(4) 0.0422(11) Uani 1 1 d . . . C11 C 0.3679(5) 0.2073(5) 1.0963(5) 0.0608(14) Uani 1 1 d . . . H11A H 0.4153 0.1750 1.0202 0.073 Uiso 1 1 calc R . . C12 C 0.4283(6) 0.1813(6) 1.2117(6) 0.0734(18) Uani 1 1 d . . . H12A H 0.5170 0.1331 1.2118 0.088 Uiso 1 1 calc R . . C13 C 0.3623(7) 0.2236(6) 1.3230(6) 0.0781(19) Uani 1 1 d . . . H13A H 0.4050 0.2067 1.3998 0.094 Uiso 1 1 calc R . . C14 C 0.2294(8) 0.2931(7) 1.3224(5) 0.086(2) Uani 1 1 d . . . H14A H 0.1814 0.3205 1.3996 0.103 Uiso 1 1 calc R . . C15 C 0.1675(6) 0.3220(5) 1.2080(5) 0.0633(14) Uani 1 1 d . . . H15A H 0.0784 0.3692 1.2080 0.076 Uiso 1 1 calc R . . C16 C 0.0680(4) 0.3642(4) 0.7125(4) 0.0410(11) Uani 1 1 d . . . C17 C 0.0301(4) 0.2397(4) 0.7720(4) 0.0369(10) Uani 1 1 d . . . C18 C 0.1146(5) 0.1182(5) 0.7624(4) 0.0456(11) Uani 1 1 d . . . C19 C 0.0718(6) 0.0034(5) 0.8050(5) 0.0620(14) Uani 1 1 d . . . H19A H 0.1302 -0.0785 0.7957 0.074 Uiso 1 1 calc R . . C20 C -0.0583(6) 0.0119(6) 0.8612(5) 0.0664(16) Uani 1 1 d . . . H20A H -0.0885 -0.0640 0.8904 0.080 Uiso 1 1 calc R . . C21 C -0.1411(5) 0.1324(6) 0.8732(4) 0.0547(13) Uani 1 1 d . . . C22 C -0.1005(5) 0.2474(5) 0.8275(4) 0.0483(12) Uani 1 1 d . . . H22A H -0.1603 0.3288 0.8342 0.058 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 Cl1 0.0670(10) 0.1405(16) 0.0793(10) 0.0089(10) 0.0103(8) -0.0652(10) Cl2 0.0500(8) 0.0750(10) 0.0865(10) 0.0015(8) 0.0053(7) -0.0094(7) S1 0.0763(10) 0.0775(10) 0.0640(9) 0.0237(7) -0.0370(7) -0.0500(8) S2 0.0719(9) 0.0666(9) 0.0655(9) 0.0210(7) -0.0294(7) -0.0476(8) O1 0.067(2) 0.080(2) 0.056(2) 0.0293(18) -0.0339(18) -0.0480(19) N1 0.054(2) 0.060(3) 0.050(2) 0.021(2) -0.0188(19) -0.034(2) N2 0.046(2) 0.066(3) 0.043(2) 0.012(2) -0.0134(18) -0.030(2) C1 0.101(5) 0.059(4) 0.064(4) 0.003(3) -0.011(3) -0.032(3) C2 0.133(7) 0.050(4) 0.083(5) 0.014(3) -0.029(5) -0.042(4) C3 0.116(6) 0.098(6) 0.081(4) 0.039(4) -0.037(4) -0.076(5) C4 0.068(4) 0.104(5) 0.098(5) 0.037(4) 0.000(3) -0.047(4) C5 0.060(4) 0.067(4) 0.089(4) 0.024(3) -0.008(3) -0.022(3) C6 0.051(3) 0.046(3) 0.049(3) 0.013(2) -0.014(2) -0.024(2) C7 0.038(2) 0.052(3) 0.046(3) 0.006(2) -0.011(2) -0.019(2) C8 0.034(2) 0.043(3) 0.042(2) 0.007(2) -0.0090(19) -0.019(2) C9 0.034(2) 0.049(3) 0.043(2) 0.003(2) -0.0070(19) -0.020(2) C10 0.048(3) 0.046(3) 0.041(3) 0.008(2) -0.009(2) -0.026(2) C11 0.045(3) 0.074(4) 0.063(3) 0.019(3) -0.005(2) -0.017(3) C12 0.057(3) 0.089(4) 0.082(4) 0.044(4) -0.028(3) -0.033(3) C13 0.103(5) 0.090(5) 0.057(4) 0.031(3) -0.040(4) -0.050(4) C14 0.111(6) 0.103(5) 0.044(3) -0.002(3) -0.008(3) -0.024(4) C15 0.064(4) 0.067(4) 0.055(3) 0.000(3) -0.004(3) -0.006(3) C16 0.038(2) 0.048(3) 0.042(3) 0.010(2) -0.006(2) -0.021(2) C17 0.040(2) 0.046(3) 0.031(2) 0.0044(19) -0.0076(18) -0.022(2) C18 0.051(3) 0.049(3) 0.041(3) 0.005(2) -0.006(2) -0.021(2) C19 0.083(4) 0.052(3) 0.056(3) 0.005(3) -0.008(3) -0.025(3) C20 0.094(5) 0.065(4) 0.055(3) 0.018(3) -0.011(3) -0.054(4) C21 0.051(3) 0.079(4) 0.045(3) 0.010(3) -0.003(2) -0.041(3) C22 0.044(3) 0.057(3) 0.049(3) 0.007(2) -0.011(2) -0.021(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 Cl1 C21 1.745(5) . ? Cl2 C18 1.742(5) . ? S1 C9 1.804(4) . ? S1 S2 2.0699(19) . ? S2 C7 1.747(4) . ? O1 C16 1.233(5) . ? N1 C7 1.323(5) . ? N1 C6 1.437(5) . ? N1 H1A 0.8600 . ? N2 C9 1.270(5) . ? N2 C10 1.418(5) . ? C1 C6 1.365(7) . ? C1 C2 1.417(8) . ? C1 H1B 0.9300 . ? C2 C3 1.355(9) . ? C2 H2B 0.9300 . ? C3 C4 1.336(9) . ? C3 H3A 0.9300 . ? C4 C5 1.388(7) . ? C4 H4A 0.9300 . ? C5 C6 1.371(7) . ? C5 H5A 0.9300 . ? C7 C8 1.399(6) . ? C8 C9 1.446(5) . ? C8 C16 1.439(5) . ? C10 C11 1.364(7) . ? C10 C15 1.381(7) . ? C11 C12 1.380(7) . ? C11 H11A 0.9300 . ? C12 C13 1.335(9) . ? C12 H12A 0.9300 . ? C13 C14 1.384(9) . ? C13 H13A 0.9300 . ? C14 C15 1.380(7) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.511(5) . ? C17 C18 1.366(6) . ? C17 C22 1.384(6) . ? C18 C19 1.388(6) . ? C19 C20 1.382(8) . ? C19 H19A 0.9300 . ? C20 C21 1.353(8) . ? C20 H20A 0.9300 . ? C21 C22 1.389(6) . ? C22 H22A 0.9300 . ? 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 C9 S1 S2 96.45(15) . . ? C7 S2 S1 95.10(16) . . ? C7 N1 C6 124.0(4) . . ? C7 N1 H1A 118.0 . . ? C6 N1 H1A 118.0 . . ? C9 N2 C10 119.8(4) . . ? C6 C1 C2 117.5(6) . . ? C6 C1 H1B 121.3 . . ? C2 C1 H1B 121.3 . . ? C3 C2 C1 120.7(6) . . ? C3 C2 H2B 119.7 . . ? C1 C2 H2B 119.7 . . ? C4 C3 C2 120.4(6) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 121.0(7) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 118.9(6) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C1 C6 C5 121.5(5) . . ? C1 C6 N1 119.3(5) . . ? C5 C6 N1 119.1(5) . . ? N1 C7 C8 126.3(4) . . ? N1 C7 S2 115.7(3) . . ? C8 C7 S2 118.0(3) . . ? C7 C8 C9 117.2(4) . . ? C7 C8 C16 119.0(4) . . ? C9 C8 C16 123.7(4) . . ? N2 C9 C8 127.0(4) . . ? N2 C9 S1 120.0(3) . . ? C8 C9 S1 113.0(3) . . ? C11 C10 C15 119.3(4) . . ? C11 C10 N2 121.1(4) . . ? C15 C10 N2 119.6(4) . . ? C10 C11 C12 120.1(5) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C13 C12 C11 121.6(6) . . ? C13 C12 H12A 119.2 . . ? C11 C12 H12A 119.2 . . ? C12 C13 C14 118.9(5) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C15 C14 C13 120.6(6) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C10 C15 C14 119.5(5) . . ? C10 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? O1 C16 C8 122.3(4) . . ? O1 C16 C17 116.4(4) . . ? C8 C16 C17 121.3(4) . . ? C18 C17 C22 118.7(4) . . ? C18 C17 C16 122.7(4) . . ? C22 C17 C16 118.3(4) . . ? C17 C18 C19 121.6(5) . . ? C17 C18 Cl2 119.3(3) . . ? C19 C18 Cl2 119.1(4) . . ? C20 C19 C18 119.4(5) . . ? C20 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? C21 C20 C19 119.0(5) . . ? C21 C20 H20A 120.5 . . ? C19 C20 H20A 120.5 . . ? C20 C21 C22 121.9(5) . . ? C20 C21 Cl1 119.3(4) . . ? C22 C21 Cl1 118.8(5) . . ? C17 C22 C21 119.3(5) . . ? C17 C22 H22A 120.3 . . ? C21 C22 H22A 120.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 S1 S2 C7 -2.6(2) . . . . ? C6 C1 C2 C3 1.2(9) . . . . ? C1 C2 C3 C4 0.7(10) . . . . ? C2 C3 C4 C5 -1.3(10) . . . . ? C3 C4 C5 C6 0.0(10) . . . . ? C2 C1 C6 C5 -2.5(8) . . . . ? C2 C1 C6 N1 179.5(5) . . . . ? C4 C5 C6 C1 2.0(8) . . . . ? C4 C5 C6 N1 180.0(5) . . . . ? C7 N1 C6 C1 -101.0(6) . . . . ? C7 N1 C6 C5 80.9(6) . . . . ? C6 N1 C7 C8 -174.4(5) . . . . ? C6 N1 C7 S2 7.0(6) . . . . ? S1 S2 C7 N1 179.4(4) . . . . ? S1 S2 C7 C8 0.8(4) . . . . ? N1 C7 C8 C9 -176.3(5) . . . . ? S2 C7 C8 C9 2.2(6) . . . . ? N1 C7 C8 C16 3.8(7) . . . . ? S2 C7 C8 C16 -177.7(3) . . . . ? C10 N2 C9 C8 176.9(4) . . . . ? C10 N2 C9 S1 -3.3(6) . . . . ? C7 C8 C9 N2 175.2(5) . . . . ? C16 C8 C9 N2 -4.8(8) . . . . ? C7 C8 C9 S1 -4.5(5) . . . . ? C16 C8 C9 S1 175.4(4) . . . . ? S2 S1 C9 N2 -175.6(4) . . . . ? S2 S1 C9 C8 4.2(3) . . . . ? C9 N2 C10 C11 -72.5(6) . . . . ? C9 N2 C10 C15 110.4(5) . . . . ? C15 C10 C11 C12 -3.1(7) . . . . ? N2 C10 C11 C12 179.8(4) . . . . ? C10 C11 C12 C13 1.4(8) . . . . ? C11 C12 C13 C14 1.2(9) . . . . ? C12 C13 C14 C15 -2.1(10) . . . . ? C11 C10 C15 C14 2.2(8) . . . . ? N2 C10 C15 C14 179.3(5) . . . . ? C13 C14 C15 C10 0.4(9) . . . . ? C7 C8 C16 O1 -9.0(7) . . . . ? C9 C8 C16 O1 171.1(5) . . . . ? C7 C8 C16 C17 169.5(4) . . . . ? C9 C8 C16 C17 -10.4(7) . . . . ? O1 C16 C17 C18 103.4(5) . . . . ? C8 C16 C17 C18 -75.2(6) . . . . ? O1 C16 C17 C22 -70.3(6) . . . . ? C8 C16 C17 C22 111.1(5) . . . . ? C22 C17 C18 C19 1.1(7) . . . . ? C16 C17 C18 C19 -172.5(4) . . . . ? C22 C17 C18 Cl2 -178.9(3) . . . . ? C16 C17 C18 Cl2 7.5(6) . . . . ? C17 C18 C19 C20 -1.6(7) . . . . ? Cl2 C18 C19 C20 178.4(4) . . . . ? C18 C19 C20 C21 0.1(7) . . . . ? C19 C20 C21 C22 1.8(8) . . . . ? C19 C20 C21 Cl1 -176.9(4) . . . . ? C18 C17 C22 C21 0.8(6) . . . . ? C16 C17 C22 C21 174.7(4) . . . . ? C20 C21 C22 C17 -2.3(7) . . . . ? Cl1 C21 C22 C17 176.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.438 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.078