# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_intermediate_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 F3 N O2 S' _chemical_formula_sum 'C10 H10 F3 N O2 S' _chemical_formula_weight 265.25 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.3006(12) _cell_length_b 12.286(4) _cell_length_c 21.406(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1131.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8198 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.22 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7797 _exptl_absorpt_correction_T_max 0.9512 _exptl_absorpt_process_details sadabs _exptl_special_details ; Saint Plus, Bruker AXS, Madison, WI, USA. ; _diffrn_ambient_temperature 200(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12963 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.23 _reflns_number_total 2664 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT, v6.45a' _computing_data_reduction 'Bruker SHELXTL XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury v2.3' _computing_publication_material 'Bruker SHELXTL XCIF' _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. Structure solved by direct methods. Flack parameter suggested incorrect absolute structure. Inverted and refinement continued. Some disorder observed in CF3 group. Site occupancies refined with common Uiso for all F atoms to 0.48:0.52. Then fixed at 50:50 sof and F refined anisotropically with restrained geometry. ; _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^)+(0.0515P)^2^+0.1338P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(9) _refine_ls_number_reflns 2664 _refine_ls_number_parameters 182 _refine_ls_number_restraints 57 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.112 _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 N1 N 0.5096(5) 0.07981(15) 0.67618(9) 0.0451(5) Uani 1 1 d . . . O1 O 0.3837(4) 0.02453(11) 0.71626(8) 0.0547(4) Uani 1 1 d . . . O2 O 0.7154(5) 0.04542(15) 0.64199(9) 0.0700(6) Uani 1 1 d . . . C1 C 0.2322(4) 0.24505(14) 0.71523(9) 0.0309(4) Uani 1 1 d . . . C2 C 0.4139(5) 0.19348(15) 0.66960(9) 0.0342(4) Uani 1 1 d . . . C3 C 0.5148(5) 0.24616(17) 0.61610(9) 0.0378(4) Uani 1 1 d . . . H3 H 0.6356 0.2083 0.5860 0.045 Uiso 1 1 calc R . . C4 C 0.4391(5) 0.35317(16) 0.60691(9) 0.0372(4) Uani 1 1 d . A . C5 C 0.2667(5) 0.40782(16) 0.65173(9) 0.0397(5) Uani 1 1 d . . . H5 H 0.2189 0.4826 0.6459 0.048 Uiso 1 1 calc R . . C6 C 0.1640(5) 0.35537(15) 0.70458(9) 0.0364(4) Uani 1 1 d . . . H6 H 0.0448 0.3944 0.7345 0.044 Uiso 1 1 calc R . . C7 C 0.5434(5) 0.4127(2) 0.54928(10) 0.0506(6) Uani 1 1 d D . . F1 F 0.7666(15) 0.3487(6) 0.5209(2) 0.0612(14) Uani 0.50 1 d PDU A 1 F2 F 0.665(2) 0.5048(7) 0.5590(4) 0.065(2) Uani 0.50 1 d PDU A 1 F3 F 0.3225(12) 0.4146(4) 0.50764(19) 0.0751(14) Uani 0.50 1 d PDU A 1 F1A F 0.6588(19) 0.3602(6) 0.5047(3) 0.085(3) Uani 0.50 1 d PDU A 2 F2A F 0.741(2) 0.4941(7) 0.5653(5) 0.063(2) Uani 0.50 1 d PDU A 2 F3A F 0.3080(11) 0.4790(4) 0.5241(2) 0.0817(16) Uani 0.50 1 d PDU A 2 S1 S 0.10151(13) 0.17823(4) 0.78271(2) 0.03727(14) Uani 1 1 d . . . C8 C -0.0666(6) 0.28767(16) 0.82804(8) 0.0363(4) Uani 1 1 d . . . H8A H 0.0869 0.3469 0.8336 0.044 Uiso 1 1 calc R . . H8B H -0.2509 0.3176 0.8063 0.044 Uiso 1 1 calc R . . C9 C -0.1603(6) 0.24156(17) 0.89126(9) 0.0453(5) Uani 1 1 d . . . H9A H -0.3253 0.1863 0.8855 0.054 Uiso 1 1 calc R . . H9B H 0.0210 0.2054 0.9108 0.054 Uiso 1 1 calc R . . C10 C -0.2781(7) 0.3311(2) 0.93395(10) 0.0564(6) Uani 1 1 d . . . H10A H -0.4620 0.3651 0.9153 0.085 Uiso 1 1 calc R . . H10B H -0.1150 0.3859 0.9395 0.085 Uiso 1 1 calc R . . H10C H -0.3333 0.3000 0.9746 0.085 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 N1 0.0522(11) 0.0362(9) 0.0470(10) -0.0106(8) -0.0089(9) 0.0072(8) O1 0.0664(10) 0.0314(7) 0.0664(10) 0.0018(7) 0.0004(10) 0.0034(7) O2 0.0834(13) 0.0565(11) 0.0703(12) -0.0088(9) 0.0113(11) 0.0311(10) C1 0.0341(9) 0.0297(8) 0.0291(8) -0.0016(7) -0.0047(8) -0.0046(7) C2 0.0346(9) 0.0316(9) 0.0363(9) -0.0056(7) -0.0067(8) 0.0006(9) C3 0.0360(10) 0.0459(11) 0.0317(9) -0.0085(8) -0.0016(8) 0.0007(8) C4 0.0384(10) 0.0443(11) 0.0289(8) -0.0006(8) -0.0020(8) -0.0066(9) C5 0.0527(12) 0.0300(10) 0.0363(10) 0.0023(8) 0.0003(9) -0.0015(9) C6 0.0467(12) 0.0303(9) 0.0322(9) -0.0013(7) 0.0014(8) 0.0009(8) C7 0.0484(13) 0.0665(16) 0.0370(11) 0.0074(10) 0.0014(10) -0.0094(12) F1 0.074(3) 0.064(2) 0.045(3) 0.005(2) 0.032(2) 0.003(2) F2 0.114(7) 0.037(2) 0.044(3) 0.008(2) 0.021(4) 0.003(3) F3 0.060(2) 0.130(4) 0.0351(18) 0.021(2) -0.0090(15) -0.006(3) F1A 0.157(8) 0.066(3) 0.033(2) -0.004(2) 0.027(3) -0.020(4) F2A 0.072(3) 0.054(4) 0.064(3) 0.020(2) -0.008(2) -0.020(3) F3A 0.056(2) 0.122(4) 0.067(3) 0.056(3) 0.006(2) 0.002(3) S1 0.0489(3) 0.0283(2) 0.0346(2) 0.00297(18) -0.0003(2) -0.0035(2) C8 0.0447(11) 0.0337(9) 0.0305(8) -0.0001(7) 0.0018(9) -0.0035(9) C9 0.0559(14) 0.0465(11) 0.0336(10) 0.0057(9) 0.0016(10) -0.0043(10) C10 0.0689(15) 0.0643(15) 0.0360(11) -0.0015(11) 0.0101(11) 0.0008(14) _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 N1 O1 1.221(3) . ? N1 O2 1.224(3) . ? N1 C2 1.463(3) . ? C1 C2 1.402(3) . ? C1 C6 1.405(3) . ? C1 S1 1.754(2) . ? C2 C3 1.385(3) . ? C3 C4 1.369(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 C7 1.503(3) . ? C5 C6 1.375(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 F1A 1.254(7) . ? C7 F2 1.264(8) . ? C7 F3 1.303(5) . ? C7 F2A 1.355(7) . ? C7 F1 1.382(6) . ? C7 F3A 1.406(5) . ? S1 C8 1.809(2) . ? C8 C9 1.521(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 O2 123.3(2) . . ? O1 N1 C2 118.29(18) . . ? O2 N1 C2 118.4(2) . . ? C2 C1 C6 116.04(17) . . ? C2 C1 S1 122.73(14) . . ? C6 C1 S1 121.21(15) . . ? C3 C2 C1 122.64(17) . . ? C3 C2 N1 115.96(18) . . ? C1 C2 N1 121.41(18) . . ? C4 C3 C2 119.56(18) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.53(18) . . ? C3 C4 C7 120.98(19) . . ? C5 C4 C7 119.48(18) . . ? C6 C5 C4 120.96(19) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 121.23(19) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? F2 C7 F3 113.5(6) . . ? F2 C7 F1 107.2(5) . . ? F3 C7 F1 102.5(3) . . ? F1A C7 F2A 108.9(6) . . ? F1A C7 F3A 106.9(4) . . ? F2A C7 F3A 97.0(5) . . ? F1A C7 C4 119.5(4) . . ? F2 C7 C4 115.1(5) . . ? F3 C7 C4 110.6(3) . . ? F2A C7 C4 109.8(5) . . ? F1 C7 C4 106.9(3) . . ? F3A C7 C4 112.4(3) . . ? C1 S1 C8 102.82(9) . . ? C9 C8 S1 107.83(14) . . ? C9 C8 H8A 110.1 . . ? S1 C8 H8A 110.1 . . ? C9 C8 H8B 110.1 . . ? S1 C8 H8B 110.1 . . ? H8A C8 H8B 108.5 . . ? C10 C9 C8 110.75(18) . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.294 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 969012' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_intermediate_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 F3 N2 S' _chemical_formula_sum 'C17 H17 F3 N2 S' _chemical_formula_weight 338.39 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.359(3) _cell_length_b 19.512(6) _cell_length_c 18.547(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3387.0(18) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5709 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8793 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details sadabs _exptl_special_details ; SAINTPlus, Bruker AXS, Madison, WI, USA ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33832 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.86 _reflns_number_total 3913 _reflns_number_gt 2979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT, v6.45a' _computing_data_reduction 'Bruker SHELXTL XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury v2.3' _computing_publication_material 'Bruker SHELXTL XCIF' _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.Structure solved by direct methods to reveal all non-H atoms. H atoms added at calculated positions. No evident problems. ; _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^)+(0.0693P)^2^+2.0381P] 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 3913 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C0 C 0.5409(2) 0.25034(10) 0.01850(10) 0.0252(4) Uani 1 1 d . . . S1 S 0.68909(6) 0.20739(3) 0.20115(3) 0.03432(17) Uani 1 1 d . . . N1 N 0.42050(19) 0.28731(9) 0.01305(10) 0.0348(4) Uani 1 1 d . . . H1C H 0.4079 0.3225 0.0403 0.042 Uiso 1 1 calc R . . H1D H 0.3560 0.2759 -0.0177 0.042 Uiso 1 1 calc R . . C1 C 0.7150(3) 0.20269(11) 0.29769(12) 0.0372(5) Uani 1 1 d . . . H1A H 0.8021 0.2265 0.3110 0.045 Uiso 1 1 calc R . . H1B H 0.6356 0.2244 0.3223 0.045 Uiso 1 1 calc R . . N2 N 0.64674(17) 0.26117(8) 0.06184(9) 0.0267(4) Uani 1 1 d . . . C2 C 0.7248(3) 0.12813(12) 0.31947(13) 0.0472(6) Uani 1 1 d . . . H2A H 0.7993 0.1060 0.2915 0.057 Uiso 1 1 calc R . . H2B H 0.6351 0.1055 0.3086 0.057 Uiso 1 1 calc R . . C3 C 0.7574(3) 0.12013(14) 0.39907(14) 0.0548(7) Uani 1 1 d . . . H3A H 0.7630 0.0723 0.4109 0.082 Uiso 1 1 calc R . . H3B H 0.6829 0.1412 0.4269 0.082 Uiso 1 1 calc R . . H3C H 0.8469 0.1418 0.4099 0.082 Uiso 1 1 calc R . . C11 C 0.6691(2) 0.29564(10) 0.18553(11) 0.0273(4) Uani 1 1 d . . . C12 C 0.6795(2) 0.34638(11) 0.23826(11) 0.0317(5) Uani 1 1 d . . . H12A H 0.6950 0.3341 0.2861 0.038 Uiso 1 1 calc R . . C13 C 0.6668(2) 0.41463(11) 0.21988(11) 0.0326(5) Uani 1 1 d . . . H13A H 0.6749 0.4482 0.2552 0.039 Uiso 1 1 calc R . . C14 C 0.6420(2) 0.43315(10) 0.14904(11) 0.0307(4) Uani 1 1 d . . . C15 C 0.6303(2) 0.38327(10) 0.09573(11) 0.0291(4) Uani 1 1 d . . . H15A H 0.6136 0.3961 0.0482 0.035 Uiso 1 1 calc R . . C16 C 0.6434(2) 0.31451(10) 0.11321(10) 0.0256(4) Uani 1 1 d . . . C17 C 0.6337(3) 0.50732(12) 0.13045(13) 0.0428(6) Uani 1 1 d . . . F1 F 0.5483(2) 0.54244(8) 0.17327(10) 0.0748(6) Uani 1 1 d . . . F2 F 0.5953(2) 0.51945(8) 0.06299(8) 0.0690(5) Uani 1 1 d . . . F3 F 0.7612(2) 0.53861(8) 0.13775(12) 0.0775(6) Uani 1 1 d . . . C21 C 0.5516(2) 0.18908(10) -0.02959(11) 0.0273(4) Uani 1 1 d . . . C22 C 0.6154(3) 0.13009(11) -0.00310(13) 0.0378(5) Uani 1 1 d . . . H22A H 0.6530 0.1298 0.0433 0.045 Uiso 1 1 calc R . . C23 C 0.6237(3) 0.07187(13) -0.04509(15) 0.0513(7) Uani 1 1 d . . . H23A H 0.6656 0.0323 -0.0267 0.062 Uiso 1 1 calc R . . C24 C 0.5700(3) 0.07224(14) -0.11432(15) 0.0519(7) Uani 1 1 d . . . H24A H 0.5762 0.0331 -0.1428 0.062 Uiso 1 1 calc R . . C25 C 0.5075(3) 0.13054(14) -0.14097(13) 0.0458(6) Uani 1 1 d . . . H25A H 0.4718 0.1308 -0.1878 0.055 Uiso 1 1 calc R . . C26 C 0.4968(2) 0.18929(12) -0.09892(11) 0.0343(5) Uani 1 1 d . . . H26A H 0.4533 0.2284 -0.1172 0.041 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 C0 0.0245(9) 0.0267(10) 0.0244(9) 0.0002(7) 0.0018(7) -0.0028(7) S1 0.0445(3) 0.0286(3) 0.0298(3) -0.0014(2) -0.0039(2) 0.0002(2) N1 0.0266(9) 0.0349(10) 0.0429(10) -0.0127(8) -0.0074(8) 0.0022(7) C1 0.0441(13) 0.0364(12) 0.0311(11) -0.0007(9) -0.0021(9) 0.0013(9) N2 0.0260(8) 0.0284(9) 0.0258(8) -0.0047(7) -0.0016(6) 0.0012(6) C2 0.0627(16) 0.0379(13) 0.0411(13) 0.0010(10) -0.0063(12) 0.0053(11) C3 0.080(2) 0.0460(15) 0.0384(13) 0.0086(11) 0.0031(13) 0.0096(14) C11 0.0237(10) 0.0291(10) 0.0290(10) -0.0015(8) 0.0007(8) -0.0014(7) C12 0.0342(11) 0.0358(11) 0.0250(10) -0.0043(8) 0.0016(8) -0.0021(9) C13 0.0340(11) 0.0345(11) 0.0292(10) -0.0098(8) 0.0028(8) -0.0022(9) C14 0.0306(10) 0.0285(10) 0.0331(11) -0.0047(8) 0.0033(8) 0.0005(8) C15 0.0280(10) 0.0325(11) 0.0269(10) -0.0031(8) 0.0007(8) 0.0007(8) C16 0.0200(9) 0.0306(10) 0.0263(10) -0.0048(8) 0.0009(7) -0.0010(7) C17 0.0572(15) 0.0325(12) 0.0386(13) -0.0046(10) 0.0038(11) 0.0032(11) F1 0.1112(15) 0.0457(9) 0.0677(11) -0.0009(8) 0.0272(10) 0.0317(9) F2 0.1236(16) 0.0383(8) 0.0451(9) 0.0028(7) -0.0148(9) 0.0111(9) F3 0.0825(13) 0.0425(9) 0.1076(15) 0.0127(9) -0.0098(11) -0.0207(9) C21 0.0204(9) 0.0343(10) 0.0273(10) -0.0044(8) 0.0014(7) -0.0054(8) C22 0.0409(12) 0.0338(11) 0.0387(12) -0.0067(9) -0.0069(10) -0.0006(9) C23 0.0554(16) 0.0363(13) 0.0622(17) -0.0145(12) -0.0089(13) 0.0054(11) C24 0.0454(14) 0.0525(16) 0.0578(16) -0.0309(13) -0.0011(12) 0.0009(12) C25 0.0339(12) 0.0717(17) 0.0317(12) -0.0207(12) -0.0006(9) -0.0038(11) C26 0.0250(10) 0.0484(13) 0.0296(11) -0.0039(9) 0.0003(8) -0.0012(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C0 N2 1.293(2) . ? C0 N1 1.342(3) . ? C0 C21 1.495(3) . ? S1 C11 1.756(2) . ? S1 C1 1.809(2) . ? N1 H1C 0.8600 . ? N1 H1D 0.8600 . ? C1 C2 1.512(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N2 C16 1.411(2) . ? C2 C3 1.516(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C11 C12 1.395(3) . ? C11 C16 1.411(3) . ? C12 C13 1.380(3) . ? C12 H12A 0.9300 . ? C13 C14 1.382(3) . ? C13 H13A 0.9300 . ? C14 C15 1.392(3) . ? C14 C17 1.490(3) . ? C15 C16 1.386(3) . ? C15 H15A 0.9300 . ? C17 F1 1.319(3) . ? C17 F2 1.323(3) . ? C17 F3 1.348(3) . ? C21 C26 1.384(3) . ? C21 C22 1.387(3) . ? C22 C23 1.379(3) . ? C22 H22A 0.9300 . ? C23 C24 1.379(4) . ? C23 H23A 0.9300 . ? C24 C25 1.371(4) . ? C24 H24A 0.9300 . ? C25 C26 1.390(3) . ? C25 H25A 0.9300 . ? C26 H26A 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 N2 C0 N1 127.04(18) . . ? N2 C0 C21 116.76(17) . . ? N1 C0 C21 116.19(16) . . ? C11 S1 C1 103.14(10) . . ? C0 N1 H1C 120.0 . . ? C0 N1 H1D 120.0 . . ? H1C N1 H1D 120.0 . . ? C2 C1 S1 108.73(16) . . ? C2 C1 H1A 109.9 . . ? S1 C1 H1A 109.9 . . ? C2 C1 H1B 109.9 . . ? S1 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C0 N2 C16 121.56(17) . . ? C1 C2 C3 111.8(2) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C12 C11 C16 119.53(19) . . ? C12 C11 S1 124.94(16) . . ? C16 C11 S1 115.52(15) . . ? C13 C12 C11 120.38(19) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 120.11(19) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C13 C14 C15 120.37(19) . . ? C13 C14 C17 118.87(19) . . ? C15 C14 C17 120.72(19) . . ? C16 C15 C14 120.26(19) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C15 C16 N2 123.92(18) . . ? C15 C16 C11 119.34(18) . . ? N2 C16 C11 116.45(17) . . ? F1 C17 F2 108.2(2) . . ? F1 C17 F3 103.9(2) . . ? F2 C17 F3 104.7(2) . . ? F1 C17 C14 113.4(2) . . ? F2 C17 C14 114.01(19) . . ? F3 C17 C14 111.8(2) . . ? C26 C21 C22 119.41(19) . . ? C26 C21 C0 121.80(19) . . ? C22 C21 C0 118.77(18) . . ? C23 C22 C21 120.5(2) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C24 C23 C22 120.1(2) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C25 C24 C23 119.7(2) . . ? C25 C24 H24A 120.1 . . ? C23 C24 H24A 120.1 . . ? C24 C25 C26 120.8(2) . . ? C24 C25 H25A 119.6 . . ? C26 C25 H25A 119.6 . . ? C21 C26 C25 119.5(2) . . ? C21 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.620 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 969013' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N2 S' _chemical_formula_sum 'C13 H10 N2 S' _chemical_formula_weight 226.29 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 P2(1)/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 6.9316(2) _cell_length_b 15.6631(5) _cell_length_c 10.3420(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.8710(18) _cell_angle_gamma 90.00 _cell_volume 1102.68(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7114 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.88 _exptl_crystal_description 'square rod' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6625 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.93 _reflns_number_total 2619 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0502P)^2^+0.3469P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2619 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.25313(6) 0.38134(3) 0.45215(4) 0.03182(14) Uani 1 1 d . . . N1 N 0.32041(19) 0.27673(9) 0.68842(13) 0.0289(3) Uani 1 1 d . . . H1N H 0.359(3) 0.2501(13) 0.765(2) 0.044(5) Uiso 1 1 d . . . N2 N 0.37662(19) 0.28554(8) 0.46979(12) 0.0295(3) Uani 1 1 d . . . C1 C 0.1360(2) 0.31851(9) 0.66797(14) 0.0269(3) Uani 1 1 d . . . C2 C 0.0797(2) 0.36707(10) 0.55435(15) 0.0285(3) Uani 1 1 d . . . C3 C -0.1060(2) 0.40459(11) 0.52641(17) 0.0333(4) Uani 1 1 d . . . H3 H -0.146(3) 0.4359(12) 0.4464(17) 0.032(4) Uiso 1 1 d . . . C4 C -0.2284(2) 0.39903(11) 0.61765(18) 0.0355(4) Uani 1 1 d . . . H4 H -0.356(3) 0.4264(12) 0.6008(17) 0.032(4) Uiso 1 1 d . . . C5 C -0.1701(2) 0.35309(11) 0.73228(17) 0.0343(4) Uani 1 1 d . . . H5 H -0.253(3) 0.3496(13) 0.7952(19) 0.042(5) Uiso 1 1 d . . . C6 C 0.0097(2) 0.31097(10) 0.75722(16) 0.0313(3) Uani 1 1 d . . . H6 H 0.052(3) 0.2750(12) 0.8349(18) 0.033(5) Uiso 1 1 d . . . C7 C 0.4023(2) 0.24940(10) 0.58411(14) 0.0271(3) Uani 1 1 d . . . C8 C 0.5292(2) 0.17210(10) 0.60526(14) 0.0288(3) Uani 1 1 d . . . C9 C 0.7056(2) 0.17104(11) 0.55902(16) 0.0345(4) Uani 1 1 d . . . H9 H 0.737(3) 0.2204(14) 0.511(2) 0.043(5) Uiso 1 1 d . . . C10 C 0.8263(3) 0.09993(13) 0.57887(19) 0.0441(4) Uani 1 1 d . . . H10 H 0.955(3) 0.1014(13) 0.549(2) 0.050(6) Uiso 1 1 d . . . C11 C 0.7710(3) 0.02885(13) 0.64242(19) 0.0468(5) Uani 1 1 d . . . H11 H 0.849(3) -0.0206(15) 0.654(2) 0.056(6) Uiso 1 1 d . . . C12 C 0.5946(3) 0.02850(12) 0.68675(19) 0.0450(4) Uani 1 1 d . . . H12 H 0.556(3) -0.0186(14) 0.731(2) 0.054(6) Uiso 1 1 d . . . C13 C 0.4747(3) 0.10028(11) 0.66984(17) 0.0366(4) Uani 1 1 d . . . H13 H 0.353(3) 0.1003(12) 0.7008(19) 0.039(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0322(2) 0.0326(2) 0.0315(2) 0.00535(15) 0.00822(16) 0.00400(15) N1 0.0265(7) 0.0352(7) 0.0245(6) 0.0011(5) 0.0037(5) 0.0059(5) N2 0.0295(7) 0.0311(7) 0.0280(7) -0.0001(5) 0.0060(5) 0.0034(5) C1 0.0229(7) 0.0280(7) 0.0290(7) -0.0027(6) 0.0027(5) 0.0003(6) C2 0.0268(7) 0.0285(7) 0.0296(7) -0.0022(6) 0.0040(6) -0.0011(6) C3 0.0285(8) 0.0312(8) 0.0383(9) 0.0027(7) 0.0014(6) 0.0013(6) C4 0.0243(8) 0.0332(8) 0.0482(10) -0.0025(7) 0.0044(7) 0.0012(6) C5 0.0266(8) 0.0384(9) 0.0393(9) -0.0038(7) 0.0098(7) -0.0004(7) C6 0.0296(8) 0.0327(8) 0.0317(8) -0.0009(7) 0.0062(6) -0.0003(6) C7 0.0242(7) 0.0295(7) 0.0272(7) -0.0028(6) 0.0042(5) -0.0005(6) C8 0.0297(8) 0.0306(8) 0.0253(7) -0.0025(6) 0.0029(6) 0.0032(6) C9 0.0344(9) 0.0347(9) 0.0357(8) -0.0018(7) 0.0098(7) 0.0035(7) C10 0.0396(10) 0.0466(10) 0.0483(11) -0.0034(8) 0.0139(8) 0.0113(8) C11 0.0562(12) 0.0408(10) 0.0434(10) 0.0016(8) 0.0091(9) 0.0193(9) C12 0.0602(12) 0.0344(9) 0.0419(10) 0.0073(8) 0.0135(9) 0.0070(8) C13 0.0400(10) 0.0366(9) 0.0344(9) 0.0020(7) 0.0101(7) 0.0023(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 S1 N2 1.7200(13) . ? S1 C2 1.7582(16) . ? N1 C7 1.3786(19) . ? N1 C1 1.4157(19) . ? N1 H1N 0.89(2) . ? N2 C7 1.2925(19) . ? C1 C6 1.392(2) . ? C1 C2 1.392(2) . ? C2 C3 1.395(2) . ? C3 C4 1.386(2) . ? C3 H3 0.957(18) . ? C4 C5 1.381(3) . ? C4 H4 0.970(19) . ? C5 C6 1.390(2) . ? C5 H5 0.95(2) . ? C6 H6 0.980(18) . ? C7 C8 1.488(2) . ? C8 C9 1.394(2) . ? C8 C13 1.396(2) . ? C9 C10 1.385(2) . ? C9 H9 0.97(2) . ? C10 C11 1.383(3) . ? C10 H10 1.00(2) . ? C11 C12 1.384(3) . ? C11 H11 0.94(2) . ? C12 C13 1.389(3) . ? C12 H12 0.93(2) . ? C13 H13 0.96(2) . ? 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 N2 S1 C2 102.03(7) . . ? C7 N1 C1 121.34(13) . . ? C7 N1 H1N 117.0(13) . . ? C1 N1 H1N 117.3(13) . . ? C7 N2 S1 117.33(11) . . ? C6 C1 C2 119.63(14) . . ? C6 C1 N1 121.66(14) . . ? C2 C1 N1 118.70(13) . . ? C1 C2 C3 120.39(15) . . ? C1 C2 S1 117.52(12) . . ? C3 C2 S1 122.06(13) . . ? C4 C3 C2 119.49(16) . . ? C4 C3 H3 120.4(11) . . ? C2 C3 H3 120.1(11) . . ? C5 C4 C3 119.99(16) . . ? C5 C4 H4 119.6(10) . . ? C3 C4 H4 120.4(10) . . ? C4 C5 C6 120.90(16) . . ? C4 C5 H5 120.1(13) . . ? C6 C5 H5 119.0(13) . . ? C5 C6 C1 119.39(15) . . ? C5 C6 H6 122.9(10) . . ? C1 C6 H6 117.7(10) . . ? N2 C7 N1 125.00(14) . . ? N2 C7 C8 117.81(13) . . ? N1 C7 C8 117.19(13) . . ? C9 C8 C13 119.23(15) . . ? C9 C8 C7 119.43(14) . . ? C13 C8 C7 121.33(14) . . ? C10 C9 C8 120.21(17) . . ? C10 C9 H9 122.0(12) . . ? C8 C9 H9 117.8(12) . . ? C11 C10 C9 120.23(18) . . ? C11 C10 H10 120.6(12) . . ? C9 C10 H10 119.1(12) . . ? C10 C11 C12 120.13(17) . . ? C10 C11 H11 121.4(14) . . ? C12 C11 H11 118.4(14) . . ? C11 C12 C13 119.97(18) . . ? C11 C12 H12 121.2(14) . . ? C13 C12 H12 118.8(14) . . ? C12 C13 C8 120.20(17) . . ? C12 C13 H13 120.1(12) . . ? C8 C13 H13 119.6(12) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.311 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 969014' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 N3 S' _chemical_formula_sum 'C12 H9 N3 S' _chemical_formula_weight 227.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2054(2) _cell_length_b 11.0782(4) _cell_length_c 15.7022(4) _cell_angle_alpha 79.2620(18) _cell_angle_beta 81.6799(18) _cell_angle_gamma 81.0105(10) _cell_volume 1040.06(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11615 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9857 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4640 _reflns_number_gt 4175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0439P)^2^+0.4837P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4640 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1_1 S 1.02683(6) 0.19248(4) 0.27486(3) 0.03792(12) Uani 1 1 d . . . N1_1 N 0.8963(2) 0.17295(13) 0.37900(9) 0.0346(3) Uani 1 1 d . . . N2_1 N 0.5515(2) 0.25187(13) 0.32742(9) 0.0327(3) Uani 1 1 d . . . H2N_1 H 0.426(4) 0.2649(19) 0.3473(13) 0.041(5) Uiso 1 1 d . . . N3_1 N 0.3547(2) 0.21576(12) 0.48942(9) 0.0322(3) Uani 1 1 d . . . C1_1 C 0.8486(2) 0.30908(14) 0.21668(10) 0.0295(3) Uani 1 1 d . . . C2_1 C 0.6259(2) 0.32549(13) 0.24944(9) 0.0278(3) Uani 1 1 d . . . C3_1 C 0.4820(3) 0.41473(14) 0.20442(10) 0.0318(3) Uani 1 1 d . . . H3_1 H 0.338(3) 0.4222(17) 0.2281(12) 0.035(5) Uiso 1 1 d . . . C4_1 C 0.5569(3) 0.48617(15) 0.12661(11) 0.0361(3) Uani 1 1 d . . . H4_1 H 0.452(4) 0.5476(19) 0.0951(13) 0.045(5) Uiso 1 1 d . . . C5_1 C 0.7775(3) 0.47059(15) 0.09424(11) 0.0379(4) Uani 1 1 d . . . H5_1 H 0.829(3) 0.5195(14) 0.0301(10) 0.022(4) Uiso 1 1 d . . . C6_1 C 0.9240(3) 0.38290(16) 0.14010(11) 0.0352(3) Uani 1 1 d . . . H6_1 H 1.077(4) 0.3704(19) 0.1184(13) 0.045(5) Uiso 1 1 d . . . C7_1 C 0.6859(2) 0.19937(13) 0.39058(10) 0.0294(3) Uani 1 1 d . . . C8_1 C 0.5674(2) 0.16769(13) 0.47979(10) 0.0284(3) Uani 1 1 d . . . C9_1 C 0.6707(3) 0.08917(14) 0.54640(10) 0.0327(3) Uani 1 1 d . . . H9_1 H 0.821(3) 0.0538(18) 0.5366(12) 0.041(5) Uiso 1 1 d . . . C10_1 C 0.5471(3) 0.05932(15) 0.62598(11) 0.0367(4) Uani 1 1 d . . . H10_1 H 0.604(4) 0.006(2) 0.6741(14) 0.052(6) Uiso 1 1 d . . . C11_1 C 0.3266(3) 0.10784(15) 0.63687(11) 0.0366(3) Uani 1 1 d . . . H11_1 H 0.244(3) 0.0909(17) 0.6871(12) 0.033(4) Uiso 1 1 d . . . C12_1 C 0.2385(3) 0.18557(15) 0.56711(11) 0.0359(3) Uani 1 1 d . . . H12_1 H 0.084(3) 0.2222(18) 0.5732(12) 0.042(5) Uiso 1 1 d . . . S1_2 S -0.04967(7) 0.72647(4) 0.15418(3) 0.04121(13) Uani 1 1 d . . . N1_2 N 0.0495(2) 0.86515(12) 0.12879(9) 0.0353(3) Uani 1 1 d . . . N2_2 N 0.3495(2) 0.78462(12) 0.21005(9) 0.0342(3) Uani 1 1 d . . . H2N_2 H 0.473(4) 0.811(2) 0.2228(14) 0.052(6) Uiso 1 1 d . . . N3_2 N 0.5201(2) 0.99284(12) 0.15785(8) 0.0302(3) Uani 1 1 d . . . C1_2 C 0.0595(3) 0.65471(14) 0.25164(11) 0.0317(3) Uani 1 1 d . . . C2_2 C 0.2513(2) 0.69154(13) 0.26955(10) 0.0301(3) Uani 1 1 d . . . C3_2 C 0.3434(3) 0.63404(15) 0.34477(11) 0.0356(3) Uani 1 1 d . . . H3_2 H 0.473(3) 0.6656(18) 0.3593(12) 0.038(5) Uiso 1 1 d . . . C4_2 C 0.2508(3) 0.53641(16) 0.39917(11) 0.0404(4) Uani 1 1 d . . . H4_2 H 0.319(4) 0.491(2) 0.4490(15) 0.056(6) Uiso 1 1 d . . . C5_2 C 0.0617(3) 0.49903(16) 0.38118(12) 0.0411(4) Uani 1 1 d . . . H5_2 H -0.007(4) 0.428(2) 0.4169(14) 0.053(6) Uiso 1 1 d . . . C6_2 C -0.0369(3) 0.56050(15) 0.30851(12) 0.0370(4) Uani 1 1 d . . . H6_2 H -0.164(4) 0.5382(18) 0.2953(13) 0.042(5) Uiso 1 1 d . . . C7_2 C 0.2323(2) 0.87357(14) 0.15562(10) 0.0285(3) Uani 1 1 d . . . C8_2 C 0.3386(2) 0.98804(13) 0.12228(9) 0.0274(3) Uani 1 1 d . . . C9_2 C 0.2582(3) 1.07905(14) 0.05649(10) 0.0322(3) Uani 1 1 d . . . H9_2 H 0.134(3) 1.0711(17) 0.0314(12) 0.034(5) Uiso 1 1 d . . . C10_2 C 0.3737(3) 1.17914(15) 0.02620(11) 0.0363(3) Uani 1 1 d . . . H10_2 H 0.329(3) 1.2447(18) -0.0235(13) 0.041(5) Uiso 1 1 d . . . C11_2 C 0.5614(3) 1.18496(15) 0.06245(11) 0.0355(3) Uani 1 1 d . . . H11_2 H 0.636(4) 1.250(2) 0.0422(14) 0.052(6) Uiso 1 1 d . . . C12_2 C 0.6286(3) 1.09037(15) 0.12745(11) 0.0334(3) Uani 1 1 d . . . H12_2 H 0.763(3) 1.0887(18) 0.1537(13) 0.044(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1_1 0.0232(2) 0.0449(2) 0.0409(2) -0.00267(17) -0.00312(15) 0.00397(16) N1_1 0.0273(6) 0.0399(7) 0.0353(7) -0.0028(6) -0.0068(5) -0.0017(5) N2_1 0.0213(6) 0.0397(7) 0.0348(7) -0.0004(5) -0.0048(5) -0.0022(5) N3_1 0.0284(6) 0.0302(6) 0.0366(7) -0.0033(5) -0.0047(5) -0.0017(5) C1_1 0.0261(7) 0.0302(7) 0.0335(7) -0.0089(6) -0.0055(6) -0.0019(6) C2_1 0.0273(7) 0.0274(7) 0.0298(7) -0.0070(5) -0.0043(6) -0.0030(5) C3_1 0.0279(8) 0.0318(7) 0.0347(8) -0.0088(6) -0.0032(6) 0.0020(6) C4_1 0.0401(9) 0.0318(8) 0.0334(8) -0.0044(6) -0.0049(7) 0.0032(7) C5_1 0.0425(9) 0.0352(8) 0.0340(8) -0.0041(6) 0.0004(7) -0.0057(7) C6_1 0.0307(8) 0.0396(8) 0.0350(8) -0.0085(7) 0.0012(6) -0.0062(6) C7_1 0.0269(7) 0.0277(7) 0.0347(8) -0.0059(6) -0.0075(6) -0.0028(6) C8_1 0.0281(7) 0.0248(7) 0.0337(7) -0.0069(5) -0.0065(6) -0.0029(5) C9_1 0.0337(8) 0.0296(7) 0.0353(8) -0.0083(6) -0.0090(6) 0.0017(6) C10_1 0.0467(10) 0.0289(7) 0.0342(8) -0.0054(6) -0.0104(7) 0.0017(7) C11_1 0.0430(9) 0.0326(8) 0.0329(8) -0.0066(6) 0.0006(7) -0.0048(7) C12_1 0.0316(8) 0.0333(8) 0.0416(9) -0.0071(7) -0.0024(7) -0.0017(6) S1_2 0.0358(2) 0.0362(2) 0.0551(3) -0.00169(18) -0.01886(19) -0.01052(17) N1_2 0.0294(7) 0.0327(7) 0.0441(7) -0.0010(6) -0.0112(6) -0.0052(5) N2_2 0.0269(7) 0.0310(6) 0.0439(7) 0.0021(5) -0.0099(6) -0.0061(5) N3_2 0.0293(6) 0.0302(6) 0.0319(6) -0.0065(5) -0.0051(5) -0.0036(5) C1_2 0.0276(7) 0.0256(7) 0.0408(8) -0.0080(6) -0.0017(6) 0.0006(6) C2_2 0.0282(7) 0.0249(7) 0.0365(8) -0.0062(6) -0.0023(6) -0.0010(6) C3_2 0.0374(9) 0.0299(7) 0.0391(8) -0.0074(6) -0.0058(7) -0.0004(6) C4_2 0.0489(10) 0.0338(8) 0.0351(8) -0.0034(7) -0.0022(7) -0.0008(7) C5_2 0.0458(10) 0.0320(8) 0.0410(9) -0.0058(7) 0.0099(7) -0.0062(7) C6_2 0.0304(8) 0.0331(8) 0.0471(9) -0.0135(7) 0.0063(7) -0.0051(6) C7_2 0.0249(7) 0.0286(7) 0.0320(7) -0.0062(6) -0.0046(6) -0.0008(5) C8_2 0.0253(7) 0.0281(7) 0.0289(7) -0.0084(5) -0.0013(5) -0.0013(5) C9_2 0.0324(8) 0.0320(8) 0.0326(7) -0.0068(6) -0.0061(6) -0.0016(6) C10_2 0.0451(9) 0.0293(7) 0.0332(8) -0.0029(6) -0.0066(7) -0.0017(7) C11_2 0.0414(9) 0.0281(7) 0.0385(8) -0.0071(6) -0.0021(7) -0.0095(7) C12_2 0.0332(8) 0.0317(8) 0.0378(8) -0.0094(6) -0.0057(6) -0.0065(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 S1_1 N1_1 1.7077(14) . ? S1_1 C1_1 1.7700(15) . ? N1_1 C7_1 1.287(2) . ? N2_1 C7_1 1.3746(19) . ? N2_1 C2_1 1.400(2) . ? N2_1 H2N_1 0.80(2) . ? N3_1 C12_1 1.337(2) . ? N3_1 C8_1 1.3422(19) . ? C1_1 C6_1 1.387(2) . ? C1_1 C2_1 1.399(2) . ? C2_1 C3_1 1.386(2) . ? C3_1 C4_1 1.388(2) . ? C3_1 H3_1 0.92(2) . ? C4_1 C5_1 1.386(2) . ? C4_1 H4_1 0.98(2) . ? C5_1 C6_1 1.393(2) . ? C5_1 H5_1 1.080(16) . ? C6_1 H6_1 0.96(2) . ? C7_1 C8_1 1.492(2) . ? C8_1 C9_1 1.394(2) . ? C9_1 C10_1 1.381(2) . ? C9_1 H9_1 0.95(2) . ? C10_1 C11_1 1.388(2) . ? C10_1 H10_1 0.94(2) . ? C11_1 C12_1 1.384(2) . ? C11_1 H11_1 0.881(19) . ? C12_1 H12_1 0.98(2) . ? S1_2 N1_2 1.7010(14) . ? S1_2 C1_2 1.7640(17) . ? N1_2 C7_2 1.288(2) . ? N2_2 C7_2 1.3683(19) . ? N2_2 C2_2 1.4071(19) . ? N2_2 H2N_2 0.92(2) . ? N3_2 C12_2 1.338(2) . ? N3_2 C8_2 1.3402(19) . ? C1_2 C6_2 1.392(2) . ? C1_2 C2_2 1.398(2) . ? C2_2 C3_2 1.389(2) . ? C3_2 C4_2 1.392(2) . ? C3_2 H3_2 0.99(2) . ? C4_2 C5_2 1.386(3) . ? C4_2 H4_2 0.96(2) . ? C5_2 C6_2 1.386(3) . ? C5_2 H5_2 0.99(2) . ? C6_2 H6_2 0.93(2) . ? C7_2 C8_2 1.494(2) . ? C8_2 C9_2 1.391(2) . ? C9_2 C10_2 1.387(2) . ? C9_2 H9_2 0.939(19) . ? C10_2 C11_2 1.383(2) . ? C10_2 H10_2 1.00(2) . ? C11_2 C12_2 1.379(2) . ? C11_2 H11_2 0.91(2) . ? C12_2 H12_2 0.98(2) . ? 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 N1_1 S1_1 C1_1 103.94(7) . . ? C7_1 N1_1 S1_1 118.54(11) . . ? C7_1 N2_1 C2_1 122.63(13) . . ? C7_1 N2_1 H2N_1 112.3(15) . . ? C2_1 N2_1 H2N_1 118.9(15) . . ? C12_1 N3_1 C8_1 117.54(13) . . ? C6_1 C1_1 C2_1 119.90(14) . . ? C6_1 C1_1 S1_1 121.74(12) . . ? C2_1 C1_1 S1_1 118.36(12) . . ? C3_1 C2_1 C1_1 119.57(14) . . ? C3_1 C2_1 N2_1 120.86(14) . . ? C1_1 C2_1 N2_1 119.57(13) . . ? C2_1 C3_1 C4_1 120.41(15) . . ? C2_1 C3_1 H3_1 116.7(11) . . ? C4_1 C3_1 H3_1 122.9(11) . . ? C5_1 C4_1 C3_1 120.14(15) . . ? C5_1 C4_1 H4_1 120.5(12) . . ? C3_1 C4_1 H4_1 119.3(12) . . ? C4_1 C5_1 C6_1 119.77(15) . . ? C4_1 C5_1 H5_1 118.7(9) . . ? C6_1 C5_1 H5_1 121.2(9) . . ? C1_1 C6_1 C5_1 120.17(15) . . ? C1_1 C6_1 H6_1 118.9(12) . . ? C5_1 C6_1 H6_1 120.9(12) . . ? N1_1 C7_1 N2_1 126.54(15) . . ? N1_1 C7_1 C8_1 118.99(13) . . ? N2_1 C7_1 C8_1 114.44(13) . . ? N3_1 C8_1 C9_1 123.22(14) . . ? N3_1 C8_1 C7_1 115.19(13) . . ? C9_1 C8_1 C7_1 121.54(14) . . ? C10_1 C9_1 C8_1 118.11(15) . . ? C10_1 C9_1 H9_1 120.8(12) . . ? C8_1 C9_1 H9_1 121.0(12) . . ? C9_1 C10_1 C11_1 119.37(15) . . ? C9_1 C10_1 H10_1 123.4(14) . . ? C11_1 C10_1 H10_1 117.2(13) . . ? C12_1 C11_1 C10_1 118.44(16) . . ? C12_1 C11_1 H11_1 120.3(12) . . ? C10_1 C11_1 H11_1 121.3(12) . . ? N3_1 C12_1 C11_1 123.32(15) . . ? N3_1 C12_1 H12_1 116.5(11) . . ? C11_1 C12_1 H12_1 120.2(11) . . ? N1_2 S1_2 C1_2 104.17(7) . . ? C7_2 N1_2 S1_2 118.34(11) . . ? C7_2 N2_2 C2_2 122.54(13) . . ? C7_2 N2_2 H2N_2 112.7(13) . . ? C2_2 N2_2 H2N_2 119.1(13) . . ? C12_2 N3_2 C8_2 117.54(13) . . ? C6_2 C1_2 C2_2 120.12(15) . . ? C6_2 C1_2 S1_2 121.42(13) . . ? C2_2 C1_2 S1_2 118.43(12) . . ? C3_2 C2_2 C1_2 119.42(14) . . ? C3_2 C2_2 N2_2 121.33(14) . . ? C1_2 C2_2 N2_2 119.24(14) . . ? C2_2 C3_2 C4_2 119.89(16) . . ? C2_2 C3_2 H3_2 118.6(11) . . ? C4_2 C3_2 H3_2 121.5(11) . . ? C5_2 C4_2 C3_2 120.74(17) . . ? C5_2 C4_2 H4_2 118.2(14) . . ? C3_2 C4_2 H4_2 121.0(14) . . ? C6_2 C5_2 C4_2 119.42(16) . . ? C6_2 C5_2 H5_2 117.1(13) . . ? C4_2 C5_2 H5_2 123.5(13) . . ? C5_2 C6_2 C1_2 120.27(16) . . ? C5_2 C6_2 H6_2 121.3(12) . . ? C1_2 C6_2 H6_2 118.4(12) . . ? N1_2 C7_2 N2_2 126.61(14) . . ? N1_2 C7_2 C8_2 118.74(13) . . ? N2_2 C7_2 C8_2 114.59(13) . . ? N3_2 C8_2 C9_2 123.37(14) . . ? N3_2 C8_2 C7_2 114.86(13) . . ? C9_2 C8_2 C7_2 121.71(13) . . ? C10_2 C9_2 C8_2 117.90(15) . . ? C10_2 C9_2 H9_2 120.9(11) . . ? C8_2 C9_2 H9_2 121.1(11) . . ? C11_2 C10_2 C9_2 119.18(15) . . ? C11_2 C10_2 H10_2 119.2(11) . . ? C9_2 C10_2 H10_2 121.5(11) . . ? C12_2 C11_2 C10_2 118.84(15) . . ? C12_2 C11_2 H11_2 122.5(14) . . ? C10_2 C11_2 H11_2 118.7(14) . . ? N3_2 C12_2 C11_2 123.15(15) . . ? N3_2 C12_2 H12_2 114.8(12) . . ? C11_2 C12_2 H12_2 122.0(12) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.335 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 969015' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 N3 S' _chemical_formula_sum 'C12 H9 N3 S' _chemical_formula_weight 227.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.8958(2) _cell_length_b 13.2251(6) _cell_length_c 15.7846(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1022.01(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11245 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 1.003 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5661 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2257 _reflns_number_gt 2012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0344P)^2^+0.4672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(11) _refine_ls_number_reflns 2257 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 S1 S 0.83003(17) 0.59498(6) 0.66557(4) 0.0433(2) Uani 1 1 d . . . N1 N 1.0272(5) 0.4385(2) 0.54044(14) 0.0399(6) Uani 1 1 d . . . H1N H 1.094(7) 0.405(3) 0.507(2) 0.050(10) Uiso 1 1 d . . . N2 N 1.0733(4) 0.50618(17) 0.67870(13) 0.0336(5) Uani 1 1 d . . . N3 N 1.6114(5) 0.21820(18) 0.60276(14) 0.0404(6) Uani 1 1 d . . . C1 C 0.8198(6) 0.50223(19) 0.51023(15) 0.0329(5) Uani 1 1 d . . . C2 C 0.7075(5) 0.57721(19) 0.56153(15) 0.0326(5) Uani 1 1 d . . . C3 C 0.4983(6) 0.6382(2) 0.53052(18) 0.0391(6) Uani 1 1 d . . . H3 H 0.411(6) 0.686(2) 0.5717(19) 0.045(9) Uiso 1 1 d . . . C4 C 0.4047(6) 0.6260(2) 0.44795(18) 0.0440(7) Uani 1 1 d . . . H4 H 0.254(7) 0.670(3) 0.425(2) 0.060(10) Uiso 1 1 d . . . C5 C 0.5195(6) 0.5521(2) 0.39697(18) 0.0415(6) Uani 1 1 d . . . H5 H 0.457(6) 0.542(2) 0.3348(19) 0.039(7) Uiso 1 1 d . . . C6 C 0.7252(6) 0.4907(2) 0.42779(16) 0.0372(6) Uani 1 1 d . . . H6 H 0.812(6) 0.442(2) 0.3903(18) 0.040(7) Uiso 1 1 d . . . C7 C 1.1385(5) 0.44292(19) 0.61979(14) 0.0296(5) Uani 1 1 d . . . C8 C 1.3511(5) 0.36671(19) 0.64103(14) 0.0295(5) Uani 1 1 d . . . C9 C 1.4245(6) 0.2904(2) 0.58539(16) 0.0370(6) Uani 1 1 d . . . H9 H 1.347(7) 0.285(2) 0.5320(17) 0.036(7) Uiso 1 1 d . . . C11 C 1.7276(6) 0.2208(2) 0.67888(17) 0.0377(6) Uani 1 1 d . . . H11 H 1.863(8) 0.167(3) 0.693(2) 0.073(11) Uiso 1 1 d . . . C12 C 1.6722(6) 0.2938(2) 0.73811(16) 0.0389(6) Uani 1 1 d . . . H12 H 1.763(6) 0.296(2) 0.7892(19) 0.039(8) Uiso 1 1 d . . . C13 C 1.4823(5) 0.3685(2) 0.71934(16) 0.0344(6) Uani 1 1 d . . . H13 H 1.436(6) 0.420(3) 0.759(2) 0.053(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0507(4) 0.0438(4) 0.0354(3) -0.0123(3) -0.0074(3) 0.0092(3) N1 0.0487(14) 0.0423(13) 0.0288(11) -0.0079(10) -0.0060(10) 0.0123(12) N2 0.0349(11) 0.0382(11) 0.0276(10) -0.0051(9) 0.0005(8) 0.0013(9) N3 0.0485(14) 0.0411(12) 0.0314(11) -0.0042(10) -0.0002(10) 0.0058(11) C1 0.0345(13) 0.0350(12) 0.0293(12) 0.0014(10) -0.0013(11) -0.0021(12) C2 0.0339(13) 0.0332(13) 0.0308(11) -0.0014(9) -0.0004(10) -0.0042(10) C3 0.0374(15) 0.0361(14) 0.0438(15) -0.0003(12) 0.0005(12) -0.0009(12) C4 0.0445(17) 0.0429(16) 0.0444(15) 0.0042(12) -0.0059(12) 0.0048(13) C5 0.0458(16) 0.0461(15) 0.0328(13) 0.0044(12) -0.0071(12) -0.0015(14) C6 0.0433(15) 0.0388(14) 0.0296(13) -0.0008(11) -0.0018(11) 0.0009(12) C7 0.0323(12) 0.0322(11) 0.0242(10) -0.0015(9) -0.0001(9) -0.0045(10) C8 0.0297(12) 0.0329(12) 0.0258(10) 0.0005(9) 0.0027(9) -0.0031(11) C9 0.0434(15) 0.0408(14) 0.0269(12) -0.0047(11) -0.0043(11) 0.0022(12) C11 0.0389(15) 0.0413(15) 0.0328(13) -0.0006(11) -0.0040(11) 0.0010(12) C12 0.0419(15) 0.0488(15) 0.0261(12) 0.0005(11) -0.0056(12) 0.0027(14) C13 0.0375(14) 0.0399(14) 0.0257(12) -0.0038(11) 0.0014(10) 0.0005(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N2 1.686(2) . ? S1 C2 1.764(2) . ? N1 C7 1.367(3) . ? N1 C1 1.403(4) . ? N1 H1N 0.76(4) . ? N2 C7 1.291(3) . ? N3 C11 1.330(3) . ? N3 C9 1.350(4) . ? C1 C6 1.389(3) . ? C1 C2 1.393(3) . ? C2 C3 1.393(4) . ? C3 C4 1.391(4) . ? C3 H3 1.00(3) . ? C4 C5 1.385(4) . ? C4 H4 1.01(3) . ? C5 C6 1.382(4) . ? C5 H5 1.04(3) . ? C6 H6 0.97(3) . ? C7 C8 1.487(4) . ? C8 C9 1.386(3) . ? C8 C13 1.393(3) . ? C9 H9 0.93(3) . ? C11 C12 1.371(4) . ? C11 H11 1.00(4) . ? C12 C13 1.388(4) . ? C12 H12 0.92(3) . ? C13 H13 0.95(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 S1 C2 105.19(11) . . ? C7 N1 C1 125.0(2) . . ? C7 N1 H1N 119(3) . . ? C1 N1 H1N 115(3) . . ? C7 N2 S1 122.52(18) . . ? C11 N3 C9 117.1(2) . . ? C6 C1 C2 119.4(2) . . ? C6 C1 N1 119.6(2) . . ? C2 C1 N1 121.0(2) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 S1 120.0(2) . . ? C1 C2 S1 120.1(2) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 122.8(18) . . ? C2 C3 H3 116.8(18) . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 119(2) . . ? C3 C4 H4 121(2) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 118.4(16) . . ? C4 C5 H5 121.2(16) . . ? C5 C6 C1 120.6(3) . . ? C5 C6 H6 119.4(18) . . ? C1 C6 H6 119.9(18) . . ? N2 C7 N1 126.1(2) . . ? N2 C7 C8 116.7(2) . . ? N1 C7 C8 117.1(2) . . ? C9 C8 C13 117.1(2) . . ? C9 C8 C7 122.2(2) . . ? C13 C8 C7 120.7(2) . . ? N3 C9 C8 124.2(2) . . ? N3 C9 H9 114.0(18) . . ? C8 C9 H9 121.8(18) . . ? N3 C11 C12 123.4(3) . . ? N3 C11 H11 118(2) . . ? C12 C11 H11 119(2) . . ? C11 C12 C13 119.2(2) . . ? C11 C12 H12 121.3(18) . . ? C13 C12 H12 119.5(18) . . ? C12 C13 C8 119.1(2) . . ? C12 C13 H13 122(2) . . ? C8 C13 H13 119(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.334 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 969016' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 N3 S' _chemical_formula_sum 'C12 H9 N3 S' _chemical_formula_weight 227.28 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 P2(1)/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 15.6603(3) _cell_length_b 7.40200(10) _cell_length_c 18.6797(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.7799(9) _cell_angle_gamma 90.00 _cell_volume 2073.11(6) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14935 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 19071 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4740 _reflns_number_gt 3958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0515P)^2^+0.8605P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4740 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1_1 S 0.16258(2) 0.37435(6) 0.31084(2) 0.03175(12) Uani 1 1 d . . . N1_1 N -0.02049(8) 0.47612(19) 0.21938(7) 0.0274(3) Uani 1 1 d . . . H1N_1 H -0.0720(13) 0.520(3) 0.1942(11) 0.037(5) Uiso 1 1 d . . . N2_1 N 0.07662(8) 0.44185(18) 0.34286(7) 0.0276(3) Uani 1 1 d . . . N3_1 N -0.21130(9) 0.5442(2) 0.39728(8) 0.0328(3) Uani 1 1 d . . . C1_1 C 0.04613(10) 0.5042(2) 0.18267(8) 0.0249(3) Uani 1 1 d . . . C2_1 C 0.13519(10) 0.4645(2) 0.21958(8) 0.0264(3) Uani 1 1 d . . . C3_1 C 0.20081(11) 0.4912(2) 0.18422(10) 0.0323(3) Uani 1 1 d . . . H3_1 H 0.2628(13) 0.463(3) 0.2102(10) 0.033(5) Uiso 1 1 d . . . C4_1 C 0.17781(12) 0.5523(2) 0.11081(10) 0.0360(4) Uani 1 1 d . . . H4_1 H 0.2252(12) 0.566(3) 0.0827(11) 0.036(5) Uiso 1 1 d . . . C5_1 C 0.08951(12) 0.5920(2) 0.07428(9) 0.0345(4) Uani 1 1 d . . . H5_1 H 0.0742(12) 0.638(3) 0.0244(11) 0.037(5) Uiso 1 1 d . . . C6_1 C 0.02354(11) 0.5704(2) 0.11034(9) 0.0299(3) Uani 1 1 d . . . H6_1 H -0.0338(13) 0.602(2) 0.0867(10) 0.029(4) Uiso 1 1 d . . . C7_1 C -0.00018(9) 0.4760(2) 0.29626(8) 0.0246(3) Uani 1 1 d . . . C8_1 C -0.07475(9) 0.5081(2) 0.32908(8) 0.0246(3) Uani 1 1 d . . . C9_1 C -0.05768(10) 0.5738(2) 0.40169(9) 0.0286(3) Uani 1 1 d . . . H9_1 H 0.0031(14) 0.607(3) 0.4289(11) 0.040(5) Uiso 1 1 d . . . C10_1 C -0.12717(11) 0.5905(2) 0.43293(9) 0.0317(3) Uani 1 1 d . . . H10_1 H -0.1181(13) 0.637(3) 0.4808(12) 0.039(5) Uiso 1 1 d . . . C12_1 C -0.22693(11) 0.4819(3) 0.32755(9) 0.0354(4) Uani 1 1 d . . . H12_1 H -0.2874(14) 0.448(3) 0.3035(11) 0.043(5) Uiso 1 1 d . . . C13_1 C -0.16230(10) 0.4635(2) 0.29099(9) 0.0311(3) Uani 1 1 d . . . H13_1 H -0.1794(13) 0.415(3) 0.2421(11) 0.038(5) Uiso 1 1 d . . . S1_2 S 0.58698(3) -0.09279(6) 0.11744(3) 0.03689(13) Uani 1 1 d . . . N1_2 N 0.39383(9) -0.0230(2) 0.09286(8) 0.0337(3) Uani 1 1 d . . . H1N_2 H 0.3376(15) -0.005(3) 0.0851(12) 0.046(6) Uiso 1 1 d . . . N2_2 N 0.50033(8) -0.19926(19) 0.05543(7) 0.0313(3) Uani 1 1 d . . . N3_2 N 0.20767(9) -0.4692(2) -0.09205(8) 0.0345(3) Uani 1 1 d . . . C1_2 C 0.44868(10) 0.1241(2) 0.12501(8) 0.0287(3) Uani 1 1 d . . . C2_2 C 0.54081(10) 0.1122(2) 0.13745(9) 0.0300(3) Uani 1 1 d . . . C3_2 C 0.59420(11) 0.2605(3) 0.16554(9) 0.0369(4) Uani 1 1 d . . . H3_2 H 0.6566(13) 0.249(3) 0.1718(11) 0.041(5) Uiso 1 1 d . . . C4_2 C 0.55657(13) 0.4170(3) 0.18450(10) 0.0406(4) Uani 1 1 d . . . H4_2 H 0.5924(15) 0.521(3) 0.2017(13) 0.057(6) Uiso 1 1 d . . . C5_2 C 0.46597(13) 0.4262(3) 0.17476(10) 0.0408(4) Uani 1 1 d . . . H5_2 H 0.4391(13) 0.532(3) 0.1849(11) 0.042(5) Uiso 1 1 d . . . C6_2 C 0.41164(11) 0.2804(2) 0.14402(9) 0.0354(4) Uani 1 1 d . . . H6_2 H 0.3490(13) 0.288(3) 0.1340(11) 0.039(5) Uiso 1 1 d . . . C7_2 C 0.41993(10) -0.1562(2) 0.05243(8) 0.0265(3) Uani 1 1 d . . . C8_2 C 0.34656(9) -0.2635(2) 0.00154(8) 0.0259(3) Uani 1 1 d . . . C9_2 C 0.35905(11) -0.4439(2) -0.01286(9) 0.0309(3) Uani 1 1 d . . . H9_2 H 0.4138(14) -0.501(3) 0.0077(11) 0.043(5) Uiso 1 1 d . . . C10_2 C 0.28850(11) -0.5404(2) -0.05885(10) 0.0347(4) Uani 1 1 d . . . H10_2 H 0.2944(12) -0.667(3) -0.0682(10) 0.035(5) Uiso 1 1 d . . . C12_2 C 0.19739(10) -0.2948(2) -0.07881(9) 0.0315(3) Uani 1 1 d . . . H12_2 H 0.1397(13) -0.240(3) -0.1054(11) 0.039(5) Uiso 1 1 d . . . C13_2 C 0.26317(10) -0.1878(2) -0.03295(8) 0.0286(3) Uani 1 1 d . . . H13_2 H 0.2525(12) -0.070(3) -0.0268(10) 0.035(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1_1 0.02417(19) 0.0408(2) 0.0291(2) 0.00354(16) 0.00577(15) 0.00676(15) N1_1 0.0201(6) 0.0348(8) 0.0262(6) 0.0003(5) 0.0050(5) 0.0011(5) N2_1 0.0238(6) 0.0321(7) 0.0269(6) 0.0002(5) 0.0074(5) -0.0012(5) N3_1 0.0273(6) 0.0391(8) 0.0341(7) 0.0062(6) 0.0120(5) 0.0019(6) C1_1 0.0265(7) 0.0221(7) 0.0275(7) -0.0021(6) 0.0098(6) -0.0005(6) C2_1 0.0267(7) 0.0237(8) 0.0291(7) -0.0018(6) 0.0086(6) 0.0000(6) C3_1 0.0289(8) 0.0314(9) 0.0393(8) -0.0034(7) 0.0139(7) -0.0007(6) C4_1 0.0396(9) 0.0342(9) 0.0408(9) -0.0005(7) 0.0218(8) -0.0009(7) C5_1 0.0466(10) 0.0309(9) 0.0300(8) 0.0017(7) 0.0174(7) 0.0011(7) C6_1 0.0329(8) 0.0269(8) 0.0294(8) -0.0002(6) 0.0082(6) 0.0038(6) C7_1 0.0247(7) 0.0219(7) 0.0269(7) -0.0007(6) 0.0070(6) -0.0031(5) C8_1 0.0246(7) 0.0216(7) 0.0278(7) 0.0034(6) 0.0076(6) -0.0010(5) C9_1 0.0266(7) 0.0292(8) 0.0297(7) -0.0008(6) 0.0076(6) -0.0019(6) C10_1 0.0312(8) 0.0350(9) 0.0302(8) -0.0003(7) 0.0108(6) 0.0007(6) C12_1 0.0235(7) 0.0480(11) 0.0338(8) 0.0041(7) 0.0072(6) -0.0033(7) C13_1 0.0264(8) 0.0389(9) 0.0268(7) 0.0013(7) 0.0058(6) -0.0043(6) S1_2 0.02197(19) 0.0392(3) 0.0464(2) -0.00717(19) 0.00492(17) 0.00040(16) N1_2 0.0237(7) 0.0381(8) 0.0419(8) -0.0135(6) 0.0138(6) -0.0045(6) N2_2 0.0247(6) 0.0326(8) 0.0355(7) -0.0044(6) 0.0071(5) -0.0001(5) N3_2 0.0290(7) 0.0366(8) 0.0362(7) -0.0088(6) 0.0066(6) -0.0007(6) C1_2 0.0291(7) 0.0329(9) 0.0242(7) -0.0033(6) 0.0077(6) -0.0043(6) C2_2 0.0290(7) 0.0335(9) 0.0272(7) -0.0002(6) 0.0073(6) -0.0027(6) C3_2 0.0308(8) 0.0418(10) 0.0351(8) -0.0016(7) 0.0048(7) -0.0083(7) C4_2 0.0452(10) 0.0343(10) 0.0367(9) -0.0040(7) 0.0030(8) -0.0096(8) C5_2 0.0499(10) 0.0324(10) 0.0378(9) -0.0063(7) 0.0089(8) 0.0010(8) C6_2 0.0327(8) 0.0379(10) 0.0352(8) -0.0063(7) 0.0093(7) 0.0008(7) C7_2 0.0260(7) 0.0271(8) 0.0278(7) -0.0005(6) 0.0101(6) -0.0011(6) C8_2 0.0245(7) 0.0289(8) 0.0259(7) -0.0012(6) 0.0096(6) -0.0010(6) C9_2 0.0254(7) 0.0325(9) 0.0338(8) -0.0013(6) 0.0072(6) 0.0032(6) C10_2 0.0335(8) 0.0287(9) 0.0411(9) -0.0079(7) 0.0094(7) 0.0005(7) C12_2 0.0264(7) 0.0366(9) 0.0298(8) -0.0017(7) 0.0052(6) 0.0030(6) C13_2 0.0282(7) 0.0276(9) 0.0304(7) -0.0018(6) 0.0089(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 S1_1 N2_1 1.6984(13) . ? S1_1 C2_1 1.7642(15) . ? N1_1 C7_1 1.3782(19) . ? N1_1 C1_1 1.4195(19) . ? N1_1 H1N_1 0.87(2) . ? N2_1 C7_1 1.2898(19) . ? N3_1 C12_1 1.336(2) . ? N3_1 C10_1 1.338(2) . ? C1_1 C6_1 1.384(2) . ? C1_1 C2_1 1.397(2) . ? C2_1 C3_1 1.387(2) . ? C3_1 C4_1 1.389(2) . ? C3_1 H3_1 0.975(19) . ? C4_1 C5_1 1.385(3) . ? C4_1 H4_1 1.031(19) . ? C5_1 C6_1 1.396(2) . ? C5_1 H5_1 0.96(2) . ? C6_1 H6_1 0.910(19) . ? C7_1 C8_1 1.486(2) . ? C8_1 C13_1 1.390(2) . ? C8_1 C9_1 1.392(2) . ? C9_1 C10_1 1.381(2) . ? C9_1 H9_1 0.97(2) . ? C10_1 H10_1 0.93(2) . ? C12_1 C13_1 1.381(2) . ? C12_1 H12_1 0.96(2) . ? C13_1 H13_1 0.94(2) . ? S1_2 N2_2 1.7019(13) . ? S1_2 C2_2 1.7665(17) . ? N1_2 C7_2 1.374(2) . ? N1_2 C1_2 1.409(2) . ? N1_2 H1N_2 0.86(2) . ? N2_2 C7_2 1.2844(19) . ? N3_2 C12_2 1.333(2) . ? N3_2 C10_2 1.346(2) . ? C1_2 C6_2 1.386(2) . ? C1_2 C2_2 1.396(2) . ? C2_2 C3_2 1.388(2) . ? C3_2 C4_2 1.392(3) . ? C3_2 H3_2 0.95(2) . ? C4_2 C5_2 1.379(3) . ? C4_2 H4_2 0.95(2) . ? C5_2 C6_2 1.392(3) . ? C5_2 H5_2 0.93(2) . ? C6_2 H6_2 0.946(19) . ? C7_2 C8_2 1.491(2) . ? C8_2 C9_2 1.387(2) . ? C8_2 C13_2 1.396(2) . ? C9_2 C10_2 1.386(2) . ? C9_2 H9_2 0.93(2) . ? C10_2 H10_2 0.96(2) . ? C12_2 C13_2 1.383(2) . ? C12_2 H12_2 0.984(19) . ? C13_2 H13_2 0.90(2) . ? 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 N2_1 S1_1 C2_1 103.46(7) . . ? C7_1 N1_1 C1_1 121.52(12) . . ? C7_1 N1_1 H1N_1 117.5(13) . . ? C1_1 N1_1 H1N_1 112.3(13) . . ? C7_1 N2_1 S1_1 119.95(11) . . ? C12_1 N3_1 C10_1 116.78(14) . . ? C6_1 C1_1 C2_1 119.59(14) . . ? C6_1 C1_1 N1_1 120.48(13) . . ? C2_1 C1_1 N1_1 119.93(13) . . ? C3_1 C2_1 C1_1 120.42(14) . . ? C3_1 C2_1 S1_1 120.48(12) . . ? C1_1 C2_1 S1_1 119.08(11) . . ? C2_1 C3_1 C4_1 120.00(15) . . ? C2_1 C3_1 H3_1 120.0(11) . . ? C4_1 C3_1 H3_1 119.9(11) . . ? C5_1 C4_1 C3_1 119.52(15) . . ? C5_1 C4_1 H4_1 119.5(10) . . ? C3_1 C4_1 H4_1 121.0(10) . . ? C4_1 C5_1 C6_1 120.71(15) . . ? C4_1 C5_1 H5_1 119.3(11) . . ? C6_1 C5_1 H5_1 119.9(11) . . ? C1_1 C6_1 C5_1 119.70(15) . . ? C1_1 C6_1 H6_1 120.3(12) . . ? C5_1 C6_1 H6_1 120.0(12) . . ? N2_1 C7_1 N1_1 126.38(14) . . ? N2_1 C7_1 C8_1 116.32(13) . . ? N1_1 C7_1 C8_1 117.20(12) . . ? C13_1 C8_1 C9_1 117.72(14) . . ? C13_1 C8_1 C7_1 121.83(14) . . ? C9_1 C8_1 C7_1 120.33(13) . . ? C10_1 C9_1 C8_1 119.34(14) . . ? C10_1 C9_1 H9_1 121.8(12) . . ? C8_1 C9_1 H9_1 118.8(12) . . ? N3_1 C10_1 C9_1 123.34(15) . . ? N3_1 C10_1 H10_1 115.4(12) . . ? C9_1 C10_1 H10_1 121.3(12) . . ? N3_1 C12_1 C13_1 124.18(15) . . ? N3_1 C12_1 H12_1 115.2(12) . . ? C13_1 C12_1 H12_1 120.6(12) . . ? C12_1 C13_1 C8_1 118.61(15) . . ? C12_1 C13_1 H13_1 118.1(12) . . ? C8_1 C13_1 H13_1 123.2(12) . . ? N2_2 S1_2 C2_2 104.31(7) . . ? C7_2 N1_2 C1_2 123.16(13) . . ? C7_2 N1_2 H1N_2 118.0(15) . . ? C1_2 N1_2 H1N_2 114.9(15) . . ? C7_2 N2_2 S1_2 119.58(12) . . ? C12_2 N3_2 C10_2 116.22(14) . . ? C6_2 C1_2 C2_2 119.92(15) . . ? C6_2 C1_2 N1_2 120.36(14) . . ? C2_2 C1_2 N1_2 119.72(15) . . ? C3_2 C2_2 C1_2 119.60(16) . . ? C3_2 C2_2 S1_2 121.37(13) . . ? C1_2 C2_2 S1_2 119.03(12) . . ? C2_2 C3_2 C4_2 120.12(16) . . ? C2_2 C3_2 H3_2 117.4(13) . . ? C4_2 C3_2 H3_2 122.4(13) . . ? C5_2 C4_2 C3_2 120.16(17) . . ? C5_2 C4_2 H4_2 119.3(14) . . ? C3_2 C4_2 H4_2 120.4(14) . . ? C4_2 C5_2 C6_2 119.97(18) . . ? C4_2 C5_2 H5_2 121.4(13) . . ? C6_2 C5_2 H5_2 118.5(13) . . ? C1_2 C6_2 C5_2 120.13(16) . . ? C1_2 C6_2 H6_2 119.2(12) . . ? C5_2 C6_2 H6_2 120.6(12) . . ? N2_2 C7_2 N1_2 126.71(14) . . ? N2_2 C7_2 C8_2 117.43(14) . . ? N1_2 C7_2 C8_2 115.84(13) . . ? C9_2 C8_2 C13_2 117.54(14) . . ? C9_2 C8_2 C7_2 120.70(13) . . ? C13_2 C8_2 C7_2 121.76(14) . . ? C10_2 C9_2 C8_2 118.98(15) . . ? C10_2 C9_2 H9_2 119.5(13) . . ? C8_2 C9_2 H9_2 121.5(13) . . ? N3_2 C10_2 C9_2 123.99(16) . . ? N3_2 C10_2 H10_2 115.1(11) . . ? C9_2 C10_2 H10_2 120.9(11) . . ? N3_2 C12_2 C13_2 124.14(15) . . ? N3_2 C12_2 H12_2 116.6(12) . . ? C13_2 C12_2 H12_2 119.2(12) . . ? C12_2 C13_2 C8_2 119.11(15) . . ? C12_2 C13_2 H13_2 120.1(12) . . ? C8_2 C13_2 H13_2 120.8(12) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.282 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 969017' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 N2 S2' _chemical_formula_sum 'C11 H8 N2 S2' _chemical_formula_weight 232.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.6844(6) _cell_length_b 10.0511(6) _cell_length_c 21.3621(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2079.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9906 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 28.40 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7321 _exptl_absorpt_correction_T_max 0.9110 _exptl_absorpt_process_details sadabs _exptl_special_details ; Saint Plus, Bruker AXS, Madison, WI, USA. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14765 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.39 _reflns_number_total 2587 _reflns_number_gt 2484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT, v7.68a' _computing_data_reduction 'Bruker SHELXTL XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury v2.3' _computing_publication_material 'Bruker SHELXTL XCIF' _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. Structure solved by direct methods to reveal all non-H atoms. H atoms added at calc positions except H1 (bound to N) which was located in difference map and freely refined. All non-H atoms refined anisotropically. ; _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^)+(0.0544P)^2^+1.9919P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2587 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 S1 S 0.02866(5) 0.15876(5) 0.44017(2) 0.02201(14) Uani 1 1 d . . . S2 S 0.28390(5) 0.18056(5) 0.26161(2) 0.03081(16) Uani 1 1 d . . . N2 N 0.18945(16) 0.39644(15) 0.41013(7) 0.0194(3) Uani 1 1 d . . . C21 C 0.30057(17) 0.29692(17) 0.32010(8) 0.0177(3) Uani 1 1 d . . . N1 N 0.16085(16) 0.16744(15) 0.38707(7) 0.0198(3) Uani 1 1 d . . . H1 H 0.225(2) 0.468(3) 0.3978(11) 0.027(6) Uiso 1 1 d . . . C17 C 0.21271(17) 0.28406(17) 0.37560(8) 0.0169(3) Uani 1 1 d . . . C16 C 0.15353(17) 0.38782(18) 0.47432(8) 0.0183(3) Uani 1 1 d . . . C12 C 0.0524(2) 0.2622(2) 0.55894(8) 0.0253(4) Uani 1 1 d . . . H12 H 0.0079 0.1840 0.5737 0.030 Uiso 1 1 calc R . . C11 C 0.08211(17) 0.27647(17) 0.49556(8) 0.0191(3) Uani 1 1 d . . . C15 C 0.18976(19) 0.48736(19) 0.51609(9) 0.0240(4) Uani 1 1 d . . . H15 H 0.2380 0.5639 0.5019 0.029 Uiso 1 1 calc R . . C14 C 0.1550(2) 0.4745(2) 0.57902(9) 0.0280(4) Uani 1 1 d . . . H14 H 0.1778 0.5437 0.6075 0.034 Uiso 1 1 calc R . . C13 C 0.0878(2) 0.3623(2) 0.60051(9) 0.0285(4) Uani 1 1 d . . . H13 H 0.0659 0.3537 0.6437 0.034 Uiso 1 1 calc R . . C22 C 0.3949(2) 0.39407(18) 0.30414(9) 0.0237(4) Uani 1 1 d . . . H22 H 0.4191 0.4667 0.3304 0.028 Uiso 1 1 calc R . . C23 C 0.4511(2) 0.3721(2) 0.24383(10) 0.0316(4) Uani 1 1 d . . . H23 H 0.5173 0.4291 0.2249 0.038 Uiso 1 1 calc R . . C24 C 0.4006(2) 0.2619(2) 0.21607(10) 0.0339(5) Uani 1 1 d . . . H24 H 0.4273 0.2329 0.1755 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0242(2) 0.0233(2) 0.0185(2) 0.00210(16) 0.00025(15) -0.00549(16) S2 0.0355(3) 0.0330(3) 0.0239(3) -0.01095(19) 0.00747(18) -0.0038(2) N2 0.0266(7) 0.0158(7) 0.0158(7) 0.0015(5) 0.0054(6) 0.0010(6) C21 0.0219(8) 0.0175(8) 0.0137(7) -0.0002(6) -0.0003(6) 0.0048(6) N1 0.0251(7) 0.0186(7) 0.0156(7) 0.0010(5) 0.0008(5) 0.0000(6) C17 0.0188(7) 0.0178(8) 0.0141(7) 0.0013(6) -0.0008(6) 0.0020(6) C16 0.0191(7) 0.0202(8) 0.0154(7) 0.0008(6) 0.0032(6) 0.0034(6) C12 0.0267(8) 0.0303(10) 0.0188(8) 0.0054(7) 0.0062(7) 0.0008(8) C11 0.0194(7) 0.0214(8) 0.0167(7) 0.0016(6) 0.0013(6) 0.0016(6) C15 0.0255(8) 0.0246(9) 0.0219(8) -0.0035(7) 0.0051(7) -0.0013(7) C14 0.0292(9) 0.0343(11) 0.0205(8) -0.0076(8) 0.0034(7) 0.0023(8) C13 0.0315(10) 0.0374(11) 0.0165(8) 0.0005(7) 0.0058(7) 0.0041(8) C22 0.0336(9) 0.0185(8) 0.0189(8) 0.0005(6) 0.0067(7) 0.0049(7) C23 0.0353(10) 0.0312(10) 0.0283(10) 0.0032(8) 0.0138(8) 0.0025(8) C24 0.0406(11) 0.0388(11) 0.0225(9) -0.0033(8) 0.0139(8) 0.0053(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.7126(16) . ? S1 C11 1.7515(18) . ? S2 C24 1.701(2) . ? S2 C21 1.7190(18) . ? N2 C17 1.368(2) . ? N2 C16 1.417(2) . ? N2 H1 0.84(3) . ? C21 C22 1.380(3) . ? C21 C17 1.465(2) . ? N1 C17 1.299(2) . ? C16 C15 1.386(2) . ? C16 C11 1.392(2) . ? C12 C13 1.385(3) . ? C12 C11 1.392(2) . ? C12 H12 0.9500 . ? C15 C14 1.392(2) . ? C15 H15 0.9500 . ? C14 C13 1.381(3) . ? C14 H14 0.9500 . ? C13 H13 0.9500 . ? C22 C23 1.416(3) . ? C22 H22 0.9500 . ? C23 C24 1.348(3) . ? C23 H23 0.9500 . ? C24 H24 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 N1 S1 C11 101.08(8) . . ? C24 S2 C21 91.50(10) . . ? C17 N2 C16 120.78(15) . . ? C17 N2 H1 117.9(17) . . ? C16 N2 H1 117.2(17) . . ? C22 C21 C17 130.30(16) . . ? C22 C21 S2 111.35(13) . . ? C17 C21 S2 118.27(13) . . ? C17 N1 S1 117.39(12) . . ? N1 C17 N2 125.45(15) . . ? N1 C17 C21 117.19(15) . . ? N2 C17 C21 117.34(15) . . ? C15 C16 C11 119.78(16) . . ? C15 C16 N2 121.11(16) . . ? C11 C16 N2 119.11(16) . . ? C13 C12 C11 119.86(18) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C11 C16 120.18(17) . . ? C12 C11 S1 121.78(14) . . ? C16 C11 S1 118.02(13) . . ? C16 C15 C14 119.57(18) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C13 C14 C15 120.72(18) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C13 C12 119.80(18) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C21 C22 C23 111.66(17) . . ? C21 C22 H22 124.2 . . ? C23 C22 H22 124.2 . . ? C24 C23 C22 112.88(19) . . ? C24 C23 H23 123.6 . . ? C22 C23 H23 123.6 . . ? C23 C24 S2 112.61(15) . . ? C23 C24 H24 123.7 . . ? S2 C24 H24 123.7 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.389 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 969018' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 N3 O2 S' _chemical_formula_sum 'C13 H9 N3 O2 S' _chemical_formula_weight 271.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 7.4294(3) _cell_length_b 12.5543(6) _cell_length_c 12.7463(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.878(3) _cell_angle_gamma 90.00 _cell_volume 1187.36(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12452 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'thin slice \w and \f scans' _diffrn_reflns_number 13481 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2090 _reflns_number_gt 1503 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0468P)^2^+1.5041P] 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 2090 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.92392(16) 0.55796(9) 0.20420(7) 0.0589(4) Uani 1 1 d . . . C1 C 0.8975(5) 0.6712(3) 0.1224(3) 0.0429(9) Uani 1 1 d . . . C2 C 0.9425(5) 0.7720(3) 0.1593(3) 0.0497(10) Uani 1 1 d . . . H2A H 0.9878 0.7811 0.2298 0.060 Uiso 1 1 calc R . . C3 C 0.9216(5) 0.8595(3) 0.0935(3) 0.0539(10) Uani 1 1 d . . . H3A H 0.9537 0.9284 0.1190 0.065 Uiso 1 1 calc R . . C4 C 0.8554(5) 0.8474(3) -0.0076(3) 0.0494(9) Uani 1 1 d . . . H4A H 0.8409 0.9078 -0.0520 0.059 Uiso 1 1 calc R . . C5 C 0.8090(5) 0.7466(3) -0.0458(3) 0.0435(9) Uani 1 1 d . . . H5A H 0.7623 0.7381 -0.1160 0.052 Uiso 1 1 calc R . . C6 C 0.8314(4) 0.6587(3) 0.0192(3) 0.0401(8) Uani 1 1 d . . . N1 N 0.7864(4) 0.5562(2) -0.0193(2) 0.0486(8) Uani 1 1 d . . . H1A H 0.7695 0.5491 -0.0878 0.058 Uiso 1 1 calc R . . C7 C 0.7669(4) 0.4672(3) 0.0406(3) 0.0397(8) Uani 1 1 d . . . N2 N 0.8136(4) 0.4583(2) 0.1388(2) 0.0489(8) Uani 1 1 d . . . C8 C 0.6896(4) 0.3724(3) -0.0152(3) 0.0386(8) Uani 1 1 d . . . C9 C 0.6091(5) 0.3796(3) -0.1159(3) 0.0457(9) Uani 1 1 d . . . H9A H 0.5971 0.4475 -0.1484 0.055 Uiso 1 1 calc R . . C10 C 0.5464(5) 0.2910(3) -0.1694(3) 0.0446(9) Uani 1 1 d . . . H10A H 0.4927 0.2969 -0.2384 0.054 Uiso 1 1 calc R . . C11 C 0.5633(4) 0.1932(3) -0.1207(3) 0.0397(8) Uani 1 1 d . . . C12 C 0.6384(5) 0.1828(3) -0.0202(3) 0.0463(9) Uani 1 1 d . . . H12A H 0.6471 0.1148 0.0122 0.056 Uiso 1 1 calc R . . C13 C 0.7009(5) 0.2721(3) 0.0325(3) 0.0442(9) Uani 1 1 d . . . H13A H 0.7522 0.2655 0.1019 0.053 Uiso 1 1 calc R . . N3 N 0.4959(4) 0.0991(2) -0.1784(2) 0.0458(8) Uani 1 1 d . . . O1 O 0.5219(4) 0.0114(2) -0.1392(2) 0.0664(8) Uani 1 1 d . . . O2 O 0.4159(4) 0.1125(2) -0.2639(2) 0.0564(7) 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 S1 0.0795(8) 0.0566(7) 0.0390(5) 0.0016(5) -0.0122(5) -0.0086(6) C1 0.037(2) 0.051(2) 0.0405(19) -0.0036(16) 0.0015(15) -0.0005(16) C2 0.046(2) 0.060(3) 0.043(2) -0.0137(18) 0.0004(16) -0.0073(19) C3 0.054(2) 0.046(2) 0.061(2) -0.0120(19) 0.0028(19) -0.0089(19) C4 0.048(2) 0.042(2) 0.058(2) 0.0005(18) 0.0027(18) -0.0012(18) C5 0.043(2) 0.041(2) 0.045(2) -0.0018(16) -0.0050(15) -0.0022(16) C6 0.036(2) 0.041(2) 0.0435(19) -0.0047(16) 0.0018(15) -0.0037(16) N1 0.069(2) 0.0421(17) 0.0341(15) -0.0024(13) -0.0054(14) -0.0100(15) C7 0.0342(19) 0.041(2) 0.0434(19) 0.0024(16) 0.0019(14) 0.0024(16) N2 0.054(2) 0.0475(19) 0.0448(17) 0.0030(14) -0.0050(14) -0.0076(15) C8 0.0322(19) 0.0388(19) 0.0449(19) 0.0041(15) 0.0022(14) -0.0020(15) C9 0.048(2) 0.036(2) 0.053(2) 0.0078(17) -0.0093(17) -0.0011(17) C10 0.045(2) 0.041(2) 0.047(2) 0.0028(16) -0.0095(16) -0.0010(17) C11 0.034(2) 0.0376(19) 0.048(2) -0.0005(16) 0.0003(15) -0.0013(15) C12 0.046(2) 0.038(2) 0.055(2) 0.0093(17) 0.0027(17) -0.0009(17) C13 0.043(2) 0.047(2) 0.0419(19) 0.0042(16) -0.0013(16) -0.0005(17) N3 0.0485(19) 0.0328(17) 0.056(2) 0.0011(14) 0.0022(15) 0.0001(14) O1 0.093(2) 0.0339(15) 0.0714(19) 0.0035(14) -0.0052(16) -0.0037(14) O2 0.0699(18) 0.0436(15) 0.0543(16) -0.0053(12) -0.0123(14) -0.0008(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N2 1.692(3) . ? S1 C1 1.768(4) . ? C1 C2 1.384(5) . ? C1 C6 1.389(5) . ? C2 C3 1.386(5) . ? C3 C4 1.365(5) . ? C4 C5 1.393(5) . ? C5 C6 1.384(5) . ? C6 N1 1.412(4) . ? N1 C7 1.365(4) . ? C7 N2 1.287(4) . ? C7 C8 1.487(5) . ? C8 C9 1.392(5) . ? C8 C13 1.399(5) . ? C9 C10 1.375(5) . ? C10 C11 1.378(5) . ? C11 C12 1.377(5) . ? C11 N3 1.467(4) . ? C12 C13 1.375(5) . ? N3 O1 1.221(4) . ? N3 O2 1.226(4) . ? C2 H2A 0.9500 . ? N1 H1A 0.8800 . ? C3 H3A 0.9500 . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C12 H12A 0.9500 . ? C13 H13A 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 N2 S1 C1 105.50(16) . . ? C2 C1 C6 119.5(3) . . ? C2 C1 S1 121.1(3) . . ? C6 C1 S1 119.4(3) . . ? C1 C2 C3 120.1(3) . . ? C4 C3 C2 120.5(4) . . ? C3 C4 C5 120.2(4) . . ? C6 C5 C4 119.6(3) . . ? C5 C6 C1 120.2(3) . . ? C5 C6 N1 119.9(3) . . ? C1 C6 N1 119.9(3) . . ? C7 N1 C6 125.5(3) . . ? N2 C7 N1 125.8(3) . . ? N2 C7 C8 118.3(3) . . ? N1 C7 C8 115.9(3) . . ? C7 N2 S1 121.0(3) . . ? C9 C8 C13 118.2(3) . . ? C9 C8 C7 121.8(3) . . ? C13 C8 C7 120.0(3) . . ? C10 C9 C8 121.6(3) . . ? C9 C10 C11 118.4(3) . . ? C12 C11 C10 121.8(3) . . ? C12 C11 N3 120.1(3) . . ? C10 C11 N3 118.0(3) . . ? C13 C12 C11 119.2(3) . . ? C12 C13 C8 120.7(3) . . ? O1 N3 O2 123.2(3) . . ? O1 N3 C11 118.6(3) . . ? O2 N3 C11 118.2(3) . . ? C6 N1 H1A 117.00 . . ? C7 N1 H1A 117.00 . . ? C1 C2 H2A 120.00 . . ? C3 C2 H2A 120.00 . . ? C2 C3 H3A 120.00 . . ? C4 C3 H3A 120.00 . . ? C3 C4 H4A 120.00 . . ? C5 C4 H4A 120.00 . . ? C4 C5 H5A 120.00 . . ? C6 C5 H5A 120.00 . . ? C8 C9 H9A 119.00 . . ? C10 C9 H9A 119.00 . . ? C9 C10 H10A 121.00 . . ? C11 C10 H10A 121.00 . . ? C11 C12 H12A 120.00 . . ? C13 C12 H12A 120.00 . . ? C8 C13 H13A 120.00 . . ? C12 C13 H13A 120.00 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.392 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 969019' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 N4 O4 S' _chemical_formula_sum 'C13 H8 N4 O4 S' _chemical_formula_weight 316.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 13.173(3) _cell_length_b 7.0180(14) _cell_length_c 14.651(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.59(3) _cell_angle_gamma 90.00 _cell_volume 1283.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6782 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 28.7 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8790 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2267 _reflns_number_gt 1982 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0766P)^2^+0.3638P] 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 2267 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 S1 S 0.41369(3) 0.84429(7) 1.12820(3) 0.02603(19) Uani 1 1 d . . . N1 N 0.51424(11) 0.7462(2) 1.09440(10) 0.0273(4) Uani 1 1 d . . . N2 N 0.42542(11) 0.8063(2) 0.92898(10) 0.0294(4) Uani 1 1 d . . . H2 H 0.4369 0.8318 0.8743 0.035 Uiso 1 1 calc R . . N3 N 0.90100(12) 0.6453(2) 1.12159(12) 0.0332(4) Uani 1 1 d . . . N4 N 0.70171(12) 0.5379(2) 0.78017(11) 0.0313(4) Uani 1 1 d . . . C11 C 0.30243(14) 0.8424(2) 1.02073(13) 0.0241(4) Uani 1 1 d . . . C12 C 0.32034(14) 0.8253(3) 0.93262(13) 0.0248(4) Uani 1 1 d . . . C13 C 0.23386(15) 0.8278(3) 0.84797(13) 0.0326(5) Uani 1 1 d . . . H13 H 0.2455 0.8136 0.7876 0.039 Uiso 1 1 calc R . . C14 C 0.13069(15) 0.8508(3) 0.85161(14) 0.0352(5) Uani 1 1 d . . . H14 H 0.0720 0.8563 0.7936 0.042 Uiso 1 1 calc R . . C15 C 0.11284(15) 0.8658(3) 0.93923(15) 0.0349(5) Uani 1 1 d . . . H15 H 0.0420 0.8806 0.9415 0.042 Uiso 1 1 calc R . . C16 C 0.19889(15) 0.8591(3) 1.02415(14) 0.0306(4) Uani 1 1 d . . . H16 H 0.1866 0.8659 1.0845 0.037 Uiso 1 1 calc R . . C20 C 0.51095(13) 0.7502(2) 1.00578(12) 0.0229(4) Uani 1 1 d . . . C21 C 0.60977(13) 0.6932(2) 0.98396(12) 0.0230(4) Uani 1 1 d . . . C22 C 0.70659(14) 0.6920(3) 1.05952(13) 0.0250(4) Uani 1 1 d . . . H22 H 0.7084 0.7228 1.1231 0.030 Uiso 1 1 calc R . . C23 C 0.79928(14) 0.6455(3) 1.04052(13) 0.0264(4) Uani 1 1 d . . . C24 C 0.80218(14) 0.5978(3) 0.94976(13) 0.0277(4) Uani 1 1 d . . . H24 H 0.8671 0.5664 0.9381 0.033 Uiso 1 1 calc R . . C25 C 0.70481(14) 0.5986(3) 0.87707(12) 0.0253(4) Uani 1 1 d . . . C26 C 0.60922(14) 0.6457(2) 0.89164(13) 0.0242(4) Uani 1 1 d . . . H26 H 0.5442 0.6456 0.8394 0.029 Uiso 1 1 calc R . . O31 O 0.98354(11) 0.6202(3) 1.10304(12) 0.0538(5) Uani 1 1 d . . . O32 O 0.89636(11) 0.6699(2) 1.20306(10) 0.0429(4) Uani 1 1 d . . . O41 O 0.78536(11) 0.4872(3) 0.76838(10) 0.0548(5) Uani 1 1 d . . . O42 O 0.61512(10) 0.5377(2) 0.71620(9) 0.0391(4) 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 S1 0.0243(3) 0.0330(3) 0.0207(3) 0.00000(16) 0.00716(19) 0.00183(17) N1 0.0246(7) 0.0325(9) 0.0240(8) 0.0020(6) 0.0069(6) 0.0032(7) N2 0.0220(7) 0.0444(10) 0.0226(7) 0.0067(7) 0.0082(6) 0.0061(7) N3 0.0219(8) 0.0377(10) 0.0355(10) -0.0045(7) 0.0027(7) 0.0028(6) N4 0.0285(8) 0.0398(10) 0.0270(8) 0.0034(7) 0.0107(6) 0.0032(7) C11 0.0248(9) 0.0224(9) 0.0241(9) 0.0004(7) 0.0062(7) 0.0011(7) C12 0.0222(9) 0.0249(10) 0.0273(9) 0.0014(7) 0.0077(7) 0.0023(7) C13 0.0286(10) 0.0440(12) 0.0235(9) -0.0022(8) 0.0062(8) 0.0066(8) C14 0.0236(9) 0.0456(13) 0.0312(10) -0.0037(8) 0.0016(8) 0.0040(8) C15 0.0226(9) 0.0416(12) 0.0403(11) -0.0011(9) 0.0098(8) 0.0032(8) C16 0.0295(10) 0.0343(11) 0.0314(10) 0.0003(8) 0.0144(8) 0.0029(8) C20 0.0213(8) 0.0217(9) 0.0244(8) 0.0019(7) 0.0056(6) -0.0001(7) C21 0.0215(8) 0.0210(9) 0.0258(9) 0.0025(7) 0.0065(7) 0.0002(7) C22 0.0262(9) 0.0243(9) 0.0234(9) -0.0013(7) 0.0063(7) -0.0002(7) C23 0.0221(9) 0.0259(10) 0.0276(9) -0.0007(7) 0.0029(7) 0.0006(7) C24 0.0220(9) 0.0277(10) 0.0342(10) 0.0011(8) 0.0100(7) 0.0011(7) C25 0.0274(9) 0.0257(10) 0.0236(8) 0.0022(7) 0.0094(7) 0.0013(7) C26 0.0228(9) 0.0234(10) 0.0241(9) 0.0032(7) 0.0042(7) 0.0002(7) O31 0.0207(7) 0.0851(13) 0.0500(9) -0.0206(8) 0.0034(6) 0.0074(7) O32 0.0322(8) 0.0654(11) 0.0254(7) -0.0045(6) 0.0012(6) 0.0037(7) O41 0.0355(8) 0.0970(14) 0.0347(8) -0.0054(8) 0.0155(6) 0.0204(9) O42 0.0300(7) 0.0617(10) 0.0242(7) -0.0003(6) 0.0067(6) -0.0010(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 S1 N1 1.7005(15) . ? S1 C11 1.7767(19) . ? N1 C20 1.286(2) . ? N2 C20 1.372(2) . ? N2 C12 1.408(2) . ? N2 H2 0.8800 . ? N3 O31 1.215(2) . ? N3 O32 1.227(2) . ? N3 C23 1.480(2) . ? N4 O41 1.222(2) . ? N4 O42 1.2239(19) . ? N4 C25 1.470(2) . ? C11 C16 1.386(3) . ? C11 C12 1.390(3) . ? C12 C13 1.391(3) . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C20 C21 1.491(2) . ? C21 C26 1.391(2) . ? C21 C22 1.397(2) . ? C22 C23 1.375(3) . ? C22 H22 0.9500 . ? C23 C24 1.384(3) . ? C24 C25 1.382(2) . ? C24 H24 0.9500 . ? C25 C26 1.383(2) . ? C26 H26 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 N1 S1 C11 103.77(8) . . ? C20 N1 S1 120.44(12) . . ? C20 N2 C12 123.79(15) . . ? C20 N2 H2 118.1 . . ? C12 N2 H2 118.1 . . ? O31 N3 O32 124.32(16) . . ? O31 N3 C23 117.81(16) . . ? O32 N3 C23 117.87(16) . . ? O41 N4 O42 123.63(16) . . ? O41 N4 C25 118.19(14) . . ? O42 N4 C25 118.16(15) . . ? C16 C11 C12 120.10(17) . . ? C16 C11 S1 120.72(14) . . ? C12 C11 S1 119.18(14) . . ? C13 C12 C11 119.59(17) . . ? C13 C12 N2 120.19(17) . . ? C11 C12 N2 120.23(16) . . ? C14 C13 C12 120.09(18) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 120.27(18) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.81(17) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.08(18) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? N1 C20 N2 126.10(16) . . ? N1 C20 C21 117.39(15) . . ? N2 C20 C21 116.49(15) . . ? C26 C21 C22 119.31(16) . . ? C26 C21 C20 122.59(15) . . ? C22 C21 C20 118.08(15) . . ? C23 C22 C21 119.09(16) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C22 C23 C24 123.38(16) . . ? C22 C23 N3 118.22(16) . . ? C24 C23 N3 118.40(16) . . ? C25 C24 C23 115.88(16) . . ? C25 C24 H24 122.1 . . ? C23 C24 H24 122.1 . . ? C24 C25 C26 123.33(17) . . ? C24 C25 N4 118.44(16) . . ? C26 C25 N4 118.16(15) . . ? C25 C26 C21 118.99(16) . . ? C25 C26 H26 120.5 . . ? C21 C26 H26 120.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.399 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 969020' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O S' _chemical_formula_sum 'C14 H12 N2 O S' _chemical_formula_weight 256.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 24.399(5) _cell_length_b 5.2540(11) _cell_length_c 9.3849(19) _cell_angle_alpha 90.00 _cell_angle_beta 95.68(3) _cell_angle_gamma 90.00 _cell_volume 1197.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 45190 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.714 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6829 _diffrn_reflns_av_R_equivalents 0.0758 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2090 _reflns_number_gt 1370 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0908P)^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 2090 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0941 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1344 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 O1 O 0.94638(8) 0.5331(4) 0.8324(2) 0.0428(6) Uani 1 1 d . . . S1 S 0.69564(3) 0.20945(17) 0.24464(10) 0.0416(3) Uani 1 1 d . . . N1 N 0.74720(10) 0.2216(5) 0.3832(3) 0.0363(7) Uani 1 1 d . . . N2 N 0.71927(10) 0.6432(5) 0.4237(3) 0.0375(7) Uani 1 1 d . . . H2 H 0.7324 0.7993 0.4251 0.045 Uiso 1 1 calc R . . C11 C 0.64406(12) 0.3937(6) 0.3142(3) 0.0362(8) Uani 1 1 d . . . C12 C 0.66219(12) 0.6016(6) 0.3984(3) 0.0349(8) Uani 1 1 d . . . C13 C 0.62423(13) 0.7535(7) 0.4575(4) 0.0440(9) Uani 1 1 d . . . H13 H 0.6363 0.8917 0.5179 0.053 Uiso 1 1 calc R . . C14 C 0.56870(14) 0.7044(7) 0.4288(4) 0.0519(10) Uani 1 1 d . . . H14 H 0.5426 0.8136 0.4663 0.062 Uiso 1 1 calc R . . C15 C 0.55064(13) 0.4971(7) 0.3457(4) 0.0506(10) Uani 1 1 d . . . H15 H 0.5123 0.4634 0.3271 0.061 Uiso 1 1 calc R . . C16 C 0.58857(13) 0.3394(7) 0.2898(4) 0.0467(9) Uani 1 1 d . . . H16 H 0.5765 0.1944 0.2349 0.056 Uiso 1 1 calc R . . C20 C 0.75482(11) 0.4384(6) 0.4466(3) 0.0320(7) Uani 1 1 d . . . C21 C 0.80396(11) 0.4728(6) 0.5505(3) 0.0319(7) Uani 1 1 d . . . C22 C 0.84708(12) 0.2962(6) 0.5528(3) 0.0355(8) Uani 1 1 d . . . H22 H 0.8442 0.1575 0.4875 0.043 Uiso 1 1 calc R . . C23 C 0.89343(12) 0.3205(6) 0.6478(4) 0.0371(8) Uani 1 1 d . . . H23 H 0.9222 0.1985 0.6482 0.044 Uiso 1 1 calc R . . C24 C 0.89828(11) 0.5229(6) 0.7433(3) 0.0340(8) Uani 1 1 d . . . C25 C 0.85597(12) 0.6989(6) 0.7440(3) 0.0362(8) Uani 1 1 d . . . H25 H 0.8590 0.8374 0.8094 0.043 Uiso 1 1 calc R . . C26 C 0.80910(12) 0.6716(6) 0.6484(3) 0.0350(8) Uani 1 1 d . . . H26 H 0.7800 0.7913 0.6500 0.042 Uiso 1 1 calc R . . C27 C 0.95263(14) 0.7445(7) 0.9282(4) 0.0489(9) Uani 1 1 d . . . H27A H 0.9525 0.9029 0.8730 0.073 Uiso 1 1 calc R . . H27B H 0.9876 0.7291 0.9887 0.073 Uiso 1 1 calc R . . H27C H 0.9221 0.7466 0.9886 0.073 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 O1 0.0462(13) 0.0377(15) 0.0430(15) -0.0066(11) -0.0037(10) 0.0038(10) S1 0.0483(5) 0.0387(6) 0.0366(5) -0.0070(4) -0.0022(3) 0.0025(4) N1 0.0416(15) 0.0287(16) 0.0378(16) -0.0027(13) 0.0006(12) 0.0013(11) N2 0.0445(15) 0.0224(15) 0.0447(18) 0.0049(12) -0.0002(12) 0.0002(12) C11 0.0445(18) 0.0288(19) 0.035(2) 0.0053(16) 0.0010(14) 0.0011(14) C12 0.0429(18) 0.0291(19) 0.0323(19) 0.0056(15) 0.0013(13) 0.0021(14) C13 0.052(2) 0.039(2) 0.041(2) -0.0017(16) 0.0033(16) 0.0059(15) C14 0.049(2) 0.046(3) 0.060(3) 0.004(2) 0.0068(18) 0.0154(17) C15 0.0396(18) 0.046(2) 0.065(3) 0.011(2) -0.0009(17) 0.0038(16) C16 0.048(2) 0.035(2) 0.055(2) 0.0077(18) -0.0048(16) -0.0015(16) C20 0.0429(17) 0.0232(18) 0.0305(18) 0.0020(14) 0.0071(13) -0.0019(13) C21 0.0382(16) 0.0252(18) 0.0328(19) 0.0009(15) 0.0060(13) -0.0035(13) C22 0.0427(18) 0.0277(19) 0.036(2) -0.0004(15) 0.0054(14) 0.0003(14) C23 0.0388(17) 0.0284(19) 0.044(2) 0.0007(16) 0.0047(14) 0.0045(14) C24 0.0352(16) 0.0309(19) 0.0357(19) 0.0023(15) 0.0022(13) -0.0024(14) C25 0.0460(19) 0.0295(19) 0.0329(19) -0.0046(15) 0.0035(14) -0.0014(14) C26 0.0394(17) 0.0295(19) 0.037(2) 0.0003(15) 0.0072(14) 0.0018(13) C27 0.052(2) 0.041(2) 0.051(2) -0.0100(18) -0.0082(16) 0.0007(16) _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 O1 C24 1.373(3) . ? O1 C27 1.428(4) . ? S1 N1 1.719(3) . ? S1 C11 1.763(3) . ? N1 C20 1.290(4) . ? N2 C20 1.385(4) . ? N2 C12 1.407(4) . ? N2 H2 0.8800 . ? C11 C16 1.381(4) . ? C11 C12 1.394(5) . ? C12 C13 1.380(4) . ? C13 C14 1.379(5) . ? C13 H13 0.9500 . ? C14 C15 1.386(5) . ? C14 H14 0.9500 . ? C15 C16 1.383(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C20 C21 1.480(4) . ? C21 C26 1.388(4) . ? C21 C22 1.401(4) . ? C22 C23 1.375(4) . ? C22 H22 0.9500 . ? C23 C24 1.388(4) . ? C23 H23 0.9500 . ? C24 C25 1.386(4) . ? C25 C26 1.389(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 C24 O1 C27 116.4(2) . . ? N1 S1 C11 101.26(14) . . ? C20 N1 S1 116.3(2) . . ? C20 N2 C12 120.0(3) . . ? C20 N2 H2 120.0 . . ? C12 N2 H2 120.0 . . ? C16 C11 C12 120.4(3) . . ? C16 C11 S1 123.3(3) . . ? C12 C11 S1 116.2(2) . . ? C13 C12 C11 119.6(3) . . ? C13 C12 N2 122.3(3) . . ? C11 C12 N2 118.1(3) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.6(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 119.7(3) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? N1 C20 N2 123.7(3) . . ? N1 C20 C21 118.8(3) . . ? N2 C20 C21 117.4(3) . . ? C26 C21 C22 118.0(3) . . ? C26 C21 C20 122.9(3) . . ? C22 C21 C20 119.1(3) . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.1(3) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? O1 C24 C25 124.3(3) . . ? O1 C24 C23 115.8(3) . . ? C25 C24 C23 119.9(3) . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C21 C26 C25 121.3(3) . . ? C21 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? O1 C27 H27A 109.5 . . ? O1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.362 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 969021' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 F3 N2 S' _chemical_formula_sum 'C14 H9 F3 N2 S' _chemical_formula_weight 294.29 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 14.857(2) _cell_length_b 13.0971(19) _cell_length_c 26.970(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.959(4) _cell_angle_gamma 90.00 _cell_volume 5247.0(13) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17034 _cell_measurement_theta_min 0.76 _cell_measurement_theta_max 25.0 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9228 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details sadabs _exptl_special_details ; This was the best set of data after studying multiple crystals which were highly twinned. Whilst these crystals also exhibited evidence for twinning, the twinning was less severe permitting the molecular structure to be solved and packing to be determined. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17034 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 0.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7611 _reflns_number_gt 7072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Structure solved by direct methods to reveal all non-H atoms with Z'=4. Initial isotropic refinement gave large residuals and evidence for non- merohedral twinning was evident in Fo > Fc for most disagreeable reflections. However no clear twin law was found in either Cell_now or using PLATON. However unreliable intensities required geometric constriatns to be applied to satisfactorily refine the structure anisotropically. All non-H atoms were refined anisotropically but with geometric restraints (SAME, DELU and EADP) for chemically equivalent atoms in each of the four independent molecules in the asymmetric unit. H atoms added at calculated positions and refined with a riding model. Evidence for a merohedral twin based on the Flack parameter was refined TWIN/BASF. ; _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^)+(0.1726P)^2^+98.2599P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 7611 _refine_ls_number_parameters 422 _refine_ls_number_restraints 326 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.3112 _refine_ls_wR_factor_gt 0.3009 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.080 _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 C10 C 0.5388(9) 0.9951(9) 0.5861(4) 0.0317(17) Uani 1 1 d D . . F11 F 0.5590(11) 0.9550(10) 0.5415(3) 0.067(4) Uani 1 1 d D . . F12 F 0.5090(8) 1.0884(8) 0.5785(6) 0.073(5) Uani 1 1 d D . . F13 F 0.6176(7) 1.0008(8) 0.6101(4) 0.041(3) Uani 1 1 d D . . S11 S 0.2847(3) 0.7409(3) 0.70571(15) 0.0263(9) Uani 1 1 d D . . N11 N 0.2976(7) 0.9613(7) 0.7094(4) 0.0219(11) Uani 1 1 d D . . H11 H 0.3142 1.0172 0.7252 0.026 Uiso 1 1 calc R . . N12 N 0.1961(7) 0.8234(7) 0.7152(4) 0.0228(12) Uani 1 1 d D . . C11 C 0.3564(9) 0.8114(8) 0.6680(5) 0.0220(12) Uani 1 1 d D . . C12 C 0.3574(8) 0.9180(8) 0.6748(4) 0.0168(12) Uani 1 1 d D . . C13 C 0.4117(9) 0.9771(8) 0.6455(4) 0.0178(13) Uani 1 1 d D . . H13 H 0.4083 1.0494 0.6478 0.021 Uiso 1 1 calc R . . C14 C 0.4725(9) 0.9320(8) 0.6120(4) 0.0221(13) Uani 1 1 d D . . C15 C 0.4735(10) 0.8259(9) 0.6074(5) 0.0267(15) Uani 1 1 d D . . H15 H 0.5151 0.7939 0.5860 0.032 Uiso 1 1 calc R . . C16 C 0.4139(9) 0.7674(9) 0.6339(5) 0.0218(13) Uani 1 1 d D . . H16 H 0.4121 0.6957 0.6288 0.026 Uiso 1 1 calc R . . C20 C 0.2150(7) 0.9199(7) 0.7192(5) 0.0174(12) Uani 1 1 d D . . C21 C 0.1423(8) 0.9903(8) 0.7338(5) 0.0199(13) Uani 1 1 d D . . C22 C 0.1345(9) 1.0879(8) 0.7130(5) 0.0208(9) Uani 1 1 d D . . H22 H 0.1784 1.1115 0.6905 0.025 Uiso 1 1 calc R . . C23 C 0.0637(10) 1.1493(10) 0.7250(6) 0.0328(12) Uani 1 1 d D . . H23 H 0.0600 1.2162 0.7115 0.039 Uiso 1 1 calc R . . C24 C -0.0017(10) 1.1161(10) 0.7561(5) 0.0303(17) Uani 1 1 d D . . H24 H -0.0518 1.1586 0.7626 0.036 Uiso 1 1 calc R . . C25 C 0.0047(10) 1.0194(10) 0.7784(6) 0.0328(12) Uani 1 1 d D . . H25 H -0.0399 0.9972 0.8008 0.039 Uiso 1 1 calc R . . C26 C 0.0748(8) 0.9585(10) 0.7676(5) 0.0208(9) Uani 1 1 d D . . H26 H 0.0794 0.8931 0.7827 0.025 Uiso 1 1 calc R . . C30 C 0.0230(9) 1.0214(9) 0.5727(4) 0.0317(17) Uani 1 1 d D . . F31 F 0.0712(11) 1.0876(9) 0.5995(4) 0.068(5) Uani 1 1 d D . . F32 F 0.0818(7) 0.9667(7) 0.5470(4) 0.036(3) Uani 1 1 d D . . F33 F -0.0244(8) 1.0779(8) 0.5412(4) 0.052(3) Uani 1 1 d D . . S31 S -0.1970(3) 0.7838(3) 0.71754(14) 0.0223(9) Uani 1 1 d D . . N31 N -0.0034(8) 0.7709(7) 0.7076(4) 0.0219(11) Uani 1 1 d D . . H31 H 0.0520 0.7837 0.7179 0.026 Uiso 1 1 calc R . . N32 N -0.1334(7) 0.6774(7) 0.7283(4) 0.0228(12) Uani 1 1 d D . . C31 C -0.1373(8) 0.8496(10) 0.6724(5) 0.0220(12) Uani 1 1 d D . . C32 C -0.0440(7) 0.8380(9) 0.6720(4) 0.0168(12) Uani 1 1 d D . . C33 C 0.0076(8) 0.8919(9) 0.6392(4) 0.0178(13) Uani 1 1 d D . . H33 H 0.0712 0.8845 0.6397 0.021 Uiso 1 1 calc R . . C34 C -0.0348(8) 0.9585(9) 0.6046(4) 0.0221(13) Uani 1 1 d D . . C35 C -0.1270(8) 0.9704(11) 0.6060(5) 0.0267(15) Uani 1 1 d D . . H35 H -0.1551 1.0193 0.5848 0.032 Uiso 1 1 calc R . . C36 C -0.1797(8) 0.9132(9) 0.6374(5) 0.0218(13) Uani 1 1 d D . . H36 H -0.2435 0.9169 0.6352 0.026 Uiso 1 1 calc R . . C40 C -0.0470(7) 0.6874(8) 0.7263(5) 0.0174(12) Uani 1 1 d D . . C41 C 0.0104(8) 0.6011(9) 0.7440(4) 0.0199(13) Uani 1 1 d D . . C42 C 0.0933(8) 0.5815(10) 0.7243(5) 0.0208(9) Uani 1 1 d D . . H42 H 0.1150 0.6259 0.6994 0.025 Uiso 1 1 calc R . . C43 C 0.1462(11) 0.5002(10) 0.7392(6) 0.0328(12) Uani 1 1 d D . . H43 H 0.2041 0.4897 0.7256 0.039 Uiso 1 1 calc R . . C44 C 0.1125(10) 0.4350(10) 0.7742(5) 0.0303(17) Uani 1 1 d D . . H44 H 0.1476 0.3782 0.7848 0.036 Uiso 1 1 calc R . . C45 C 0.0275(10) 0.4505(11) 0.7944(6) 0.0328(12) Uani 1 1 d D . . H45 H 0.0054 0.4036 0.8181 0.039 Uiso 1 1 calc R . . C46 C -0.0248(9) 0.5334(9) 0.7803(5) 0.0208(9) Uani 1 1 d D . . H46 H -0.0822 0.5447 0.7942 0.025 Uiso 1 1 calc R . . C50 C 0.2231(9) 0.7477(9) 0.5415(4) 0.0317(17) Uani 1 1 d D . . F51 F 0.2029(10) 0.7890(10) 0.5855(4) 0.060(4) Uani 1 1 d D . . F52 F 0.2511(11) 0.6541(7) 0.5512(5) 0.074(5) Uani 1 1 d D . . F53 F 0.1449(7) 0.7394(9) 0.5175(4) 0.043(3) Uani 1 1 d D . . S51 S 0.4772(3) 0.9956(3) 0.41960(17) 0.0266(10) Uani 1 1 d D . . N51 N 0.4629(7) 0.7728(8) 0.4200(4) 0.0219(11) Uani 1 1 d D . . H51 H 0.4473 0.7137 0.4070 0.026 Uiso 1 1 calc R . . N52 N 0.5633(7) 0.9121(7) 0.4091(4) 0.0228(12) Uani 1 1 d D . . C51 C 0.4056(9) 0.9259(8) 0.4578(5) 0.0220(12) Uani 1 1 d D . . C52 C 0.4045(9) 0.8193(7) 0.4542(4) 0.0168(12) Uani 1 1 d D . . C53 C 0.3477(9) 0.7594(8) 0.4813(4) 0.0178(13) Uani 1 1 d D . . H53 H 0.3483 0.6871 0.4783 0.021 Uiso 1 1 calc R . . C54 C 0.2882(9) 0.8095(8) 0.5139(4) 0.0221(13) Uani 1 1 d D . . C55 C 0.2897(10) 0.9152(8) 0.5190(5) 0.0267(15) Uani 1 1 d D . . H55 H 0.2486 0.9482 0.5403 0.032 Uiso 1 1 calc R . . C56 C 0.3514(9) 0.9719(9) 0.4929(5) 0.0218(13) Uani 1 1 d D . . H56 H 0.3569 1.0431 0.4990 0.026 Uiso 1 1 calc R . . C60 C 0.5431(7) 0.8158(7) 0.4062(5) 0.0174(12) Uani 1 1 d D . . C61 C 0.6143(9) 0.7453(8) 0.3897(5) 0.0199(13) Uani 1 1 d D . . C62 C 0.6267(9) 0.6484(9) 0.4102(5) 0.0208(9) Uani 1 1 d D . . H62 H 0.5852 0.6247 0.4340 0.025 Uiso 1 1 calc R . . C63 C 0.6967(10) 0.5864(10) 0.3972(5) 0.0328(12) Uani 1 1 d D . . H63 H 0.7042 0.5218 0.4128 0.039 Uiso 1 1 calc R . . C64 C 0.7558(10) 0.6175(10) 0.3618(5) 0.0303(17) Uani 1 1 d D . . H64 H 0.8030 0.5737 0.3516 0.036 Uiso 1 1 calc R . . C65 C 0.7454(10) 0.7157(10) 0.3407(5) 0.0328(12) Uani 1 1 d D . . H65 H 0.7884 0.7391 0.3176 0.039 Uiso 1 1 calc R . . C66 C 0.6750(8) 0.7777(9) 0.3527(5) 0.0208(9) Uani 1 1 d D . . H66 H 0.6668 0.8416 0.3365 0.025 Uiso 1 1 calc R . . C70 C 0.2346(9) 0.2163(9) 0.5506(4) 0.0317(17) Uani 1 1 d D . . F71 F 0.2802(9) 0.1581(9) 0.5833(4) 0.062(4) Uani 1 1 d D . . F72 F 0.1843(10) 0.1512(9) 0.5248(4) 0.067(4) Uani 1 1 d D . . F73 F 0.1804(9) 0.2714(7) 0.5777(4) 0.049(3) Uani 1 1 d D . . S71 S 0.4614(2) 0.4520(3) 0.40978(14) 0.0215(8) Uani 1 1 d D . . N71 N 0.2632(8) 0.4655(7) 0.4170(4) 0.0219(11) Uani 1 1 d D . . H71 H 0.2077 0.4545 0.4063 0.026 Uiso 1 1 calc R . . N72 N 0.3960(7) 0.5582(7) 0.3981(4) 0.0228(12) Uani 1 1 d D . . C71 C 0.3974(8) 0.3876(10) 0.4535(5) 0.0220(12) Uani 1 1 d D . . C72 C 0.3044(7) 0.3958(8) 0.4514(4) 0.0168(12) Uani 1 1 d D . . C73 C 0.2505(8) 0.3448(9) 0.4846(4) 0.0178(13) Uani 1 1 d D . . H73 H 0.1873 0.3556 0.4850 0.021 Uiso 1 1 calc R . . C74 C 0.2935(8) 0.2753(9) 0.5181(4) 0.0221(13) Uani 1 1 d D . . C75 C 0.3861(8) 0.2662(11) 0.5205(5) 0.0267(15) Uani 1 1 d D . . H75 H 0.4138 0.2227 0.5444 0.032 Uiso 1 1 calc R . . C76 C 0.4385(8) 0.3214(10) 0.4876(5) 0.0218(13) Uani 1 1 d D . . H76 H 0.5022 0.3141 0.4883 0.026 Uiso 1 1 calc R . . C80 C 0.3094(7) 0.5492(8) 0.4004(5) 0.0174(12) Uani 1 1 d D . . C81 C 0.2532(8) 0.6384(9) 0.3859(5) 0.0199(13) Uani 1 1 d D . . C82 C 0.1691(8) 0.6571(10) 0.4036(5) 0.0208(9) Uani 1 1 d D . . H82 H 0.1439 0.6107 0.4266 0.025 Uiso 1 1 calc R . . C83 C 0.1201(11) 0.7409(10) 0.3890(6) 0.0328(12) Uani 1 1 d D . . H83 H 0.0608 0.7498 0.4009 0.039 Uiso 1 1 calc R . . C84 C 0.1558(10) 0.8127(10) 0.3573(6) 0.0303(17) Uani 1 1 d D . . H84 H 0.1232 0.8727 0.3488 0.036 Uiso 1 1 calc R . . C85 C 0.2414(10) 0.7945(10) 0.3380(6) 0.0328(12) Uani 1 1 d D . . H85 H 0.2672 0.8423 0.3158 0.039 Uiso 1 1 calc R . . C86 C 0.2880(9) 0.7078(9) 0.3511(5) 0.0208(9) Uani 1 1 d D . . H86 H 0.3445 0.6943 0.3365 0.025 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 C10 0.050(5) 0.024(3) 0.021(3) 0.014(3) 0.000(3) 0.013(3) F11 0.102(13) 0.078(9) 0.022(5) 0.001(6) 0.007(7) -0.042(8) F12 0.031(7) 0.055(7) 0.134(13) 0.065(8) 0.035(8) 0.026(6) F13 0.035(6) 0.049(6) 0.038(6) -0.003(5) 0.004(5) 0.001(5) S11 0.030(2) 0.0151(16) 0.0336(19) 0.0006(14) 0.0040(18) 0.0020(16) N11 0.028(3) 0.012(2) 0.025(2) 0.003(2) -0.005(2) -0.004(2) N12 0.034(3) 0.015(2) 0.019(2) 0.0022(19) 0.004(2) 0.004(2) C11 0.025(3) 0.016(3) 0.025(3) 0.000(2) 0.000(3) -0.005(3) C12 0.015(3) 0.014(2) 0.022(3) -0.003(2) -0.001(3) 0.002(2) C13 0.019(3) 0.012(3) 0.022(3) -0.002(2) -0.002(3) 0.002(2) C14 0.033(4) 0.015(3) 0.018(3) -0.004(2) -0.006(3) -0.001(3) C15 0.031(4) 0.021(3) 0.028(3) -0.001(2) -0.002(3) 0.008(3) C16 0.015(3) 0.018(3) 0.033(3) -0.002(2) 0.000(3) 0.009(2) C20 0.018(3) 0.015(2) 0.020(3) -0.004(2) -0.007(3) -0.002(2) C21 0.022(4) 0.021(3) 0.016(3) -0.002(2) -0.003(3) 0.001(3) C22 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C23 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C24 0.033(4) 0.024(3) 0.034(4) -0.006(3) -0.008(3) 0.014(3) C25 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C26 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C30 0.050(5) 0.024(3) 0.021(3) 0.014(3) 0.000(3) 0.013(3) F31 0.132(14) 0.051(7) 0.022(5) -0.003(5) 0.010(7) -0.057(8) F32 0.038(7) 0.027(5) 0.044(6) 0.004(4) 0.014(5) 0.008(5) F33 0.057(8) 0.052(6) 0.050(6) 0.029(5) 0.035(6) 0.030(6) S31 0.021(2) 0.0136(15) 0.032(2) 0.0071(14) 0.0032(18) -0.0011(15) N31 0.028(3) 0.012(2) 0.025(2) 0.003(2) -0.005(2) -0.004(2) N32 0.034(3) 0.015(2) 0.019(2) 0.0022(19) 0.004(2) 0.004(2) C31 0.025(3) 0.016(3) 0.025(3) 0.000(2) 0.000(3) -0.005(3) C32 0.015(3) 0.014(2) 0.022(3) -0.003(2) -0.001(3) 0.002(2) C33 0.019(3) 0.012(3) 0.022(3) -0.002(2) -0.002(3) 0.002(2) C34 0.033(4) 0.015(3) 0.018(3) -0.004(2) -0.006(3) -0.001(3) C35 0.031(4) 0.021(3) 0.028(3) -0.001(2) -0.002(3) 0.008(3) C36 0.015(3) 0.018(3) 0.033(3) -0.002(2) 0.000(3) 0.009(2) C40 0.018(3) 0.015(2) 0.020(3) -0.004(2) -0.007(3) -0.002(2) C41 0.022(4) 0.021(3) 0.016(3) -0.002(2) -0.003(3) 0.001(3) C42 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C43 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C44 0.033(4) 0.024(3) 0.034(4) -0.006(3) -0.008(3) 0.014(3) C45 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C46 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C50 0.050(5) 0.024(3) 0.021(3) 0.014(3) 0.000(3) 0.013(3) F51 0.078(11) 0.081(10) 0.020(5) -0.005(5) 0.015(6) 0.005(8) F52 0.117(14) 0.029(6) 0.078(9) 0.035(6) 0.035(9) 0.014(7) F53 0.042(7) 0.054(7) 0.033(5) 0.023(5) -0.011(5) -0.015(5) S51 0.023(2) 0.0145(17) 0.042(2) 0.0045(15) -0.0050(19) 0.0036(16) N51 0.028(3) 0.012(2) 0.025(2) 0.003(2) -0.005(2) -0.004(2) N52 0.034(3) 0.015(2) 0.019(2) 0.0022(19) 0.004(2) 0.004(2) C51 0.025(3) 0.016(3) 0.025(3) 0.000(2) 0.000(3) -0.005(3) C52 0.015(3) 0.014(2) 0.022(3) -0.003(2) -0.001(3) 0.002(2) C53 0.019(3) 0.012(3) 0.022(3) -0.002(2) -0.002(3) 0.002(2) C54 0.033(4) 0.015(3) 0.018(3) -0.004(2) -0.006(3) -0.001(3) C55 0.031(4) 0.021(3) 0.028(3) -0.001(2) -0.002(3) 0.008(3) C56 0.015(3) 0.018(3) 0.033(3) -0.002(2) 0.000(3) 0.009(2) C60 0.018(3) 0.015(2) 0.020(3) -0.004(2) -0.007(3) -0.002(2) C61 0.022(4) 0.021(3) 0.016(3) -0.002(2) -0.003(3) 0.001(3) C62 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C63 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C64 0.033(4) 0.024(3) 0.034(4) -0.006(3) -0.008(3) 0.014(3) C65 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C66 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C70 0.050(5) 0.024(3) 0.021(3) 0.014(3) 0.000(3) 0.013(3) F71 0.061(9) 0.064(7) 0.060(7) 0.045(6) 0.005(7) 0.002(7) F72 0.104(12) 0.059(8) 0.040(6) -0.009(5) 0.027(7) -0.062(8) F73 0.064(9) 0.023(5) 0.062(7) 0.009(5) 0.034(7) 0.001(5) S71 0.0077(17) 0.0205(18) 0.037(2) 0.0076(14) 0.0104(17) 0.0058(14) N71 0.028(3) 0.012(2) 0.025(2) 0.003(2) -0.005(2) -0.004(2) N72 0.034(3) 0.015(2) 0.019(2) 0.0022(19) 0.004(2) 0.004(2) C71 0.025(3) 0.016(3) 0.025(3) 0.000(2) 0.000(3) -0.005(3) C72 0.015(3) 0.014(2) 0.022(3) -0.003(2) -0.001(3) 0.002(2) C73 0.019(3) 0.012(3) 0.022(3) -0.002(2) -0.002(3) 0.002(2) C74 0.033(4) 0.015(3) 0.018(3) -0.004(2) -0.006(3) -0.001(3) C75 0.031(4) 0.021(3) 0.028(3) -0.001(2) -0.002(3) 0.008(3) C76 0.015(3) 0.018(3) 0.033(3) -0.002(2) 0.000(3) 0.009(2) C80 0.018(3) 0.015(2) 0.020(3) -0.004(2) -0.007(3) -0.002(2) C81 0.022(4) 0.021(3) 0.016(3) -0.002(2) -0.003(3) 0.001(3) C82 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) C83 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C84 0.033(4) 0.024(3) 0.034(4) -0.006(3) -0.008(3) 0.014(3) C85 0.043(3) 0.028(2) 0.027(2) -0.003(2) -0.004(2) 0.004(2) C86 0.018(2) 0.022(2) 0.022(2) -0.0019(17) -0.0023(19) 0.0038(19) _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 C10 F12 1.314(12) . ? C10 F13 1.331(13) . ? C10 F11 1.349(13) . ? C10 C14 1.472(13) . ? S11 N12 1.726(10) . ? S11 C11 1.749(10) . ? N11 C20 1.372(12) . ? N11 C12 1.417(12) . ? N11 H11 0.8800 . ? N12 C20 1.298(12) . ? C11 C16 1.390(13) . ? C11 C12 1.408(12) . ? C12 C13 1.377(12) . ? C13 C14 1.418(13) . ? C13 H13 0.9500 . ? C14 C15 1.395(13) . ? C15 C16 1.379(14) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C20 C21 1.479(12) . ? C21 C22 1.401(13) . ? C21 C26 1.428(13) . ? C22 C23 1.367(14) . ? C22 H22 0.9500 . ? C23 C24 1.365(15) . ? C23 H23 0.9500 . ? C24 C25 1.404(14) . ? C24 H24 0.9500 . ? C25 C26 1.349(14) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C30 F33 1.320(13) . ? C30 F32 1.332(14) . ? C30 F31 1.332(14) . ? C30 C34 1.478(13) . ? S31 N32 1.705(9) . ? S31 C31 1.746(10) . ? N31 C40 1.373(12) . ? N31 C32 1.427(11) . ? N31 H31 0.8800 . ? N32 C40 1.292(12) . ? C31 C32 1.394(13) . ? C31 C36 1.401(13) . ? C32 C33 1.375(13) . ? C33 C34 1.416(12) . ? C33 H33 0.9500 . ? C34 C35 1.380(13) . ? C35 C36 1.383(14) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C40 C41 1.490(12) . ? C41 C42 1.372(13) . ? C41 C46 1.426(13) . ? C42 C43 1.379(14) . ? C42 H42 0.9500 . ? C43 C44 1.374(14) . ? C43 H43 0.9500 . ? C44 C45 1.399(14) . ? C44 H44 0.9500 . ? C45 C46 1.384(13) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C50 F52 1.318(13) . ? C50 F53 1.326(13) . ? C50 F51 1.343(13) . ? C50 C54 1.473(13) . ? S51 N52 1.709(9) . ? S51 C51 1.750(10) . ? N51 C60 1.374(12) . ? N51 C52 1.415(12) . ? N51 H51 0.8800 . ? N52 C60 1.299(12) . ? C51 C56 1.390(13) . ? C51 C52 1.400(12) . ? C52 C53 1.371(13) . ? C53 C54 1.420(13) . ? C53 H53 0.9500 . ? C54 C55 1.390(13) . ? C55 C56 1.382(14) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C60 C61 1.478(12) . ? C61 C62 1.395(13) . ? C61 C66 1.422(13) . ? C62 C63 1.370(14) . ? C62 H62 0.9500 . ? C63 C64 1.370(15) . ? C63 H63 0.9500 . ? C64 C65 1.415(14) . ? C64 H64 0.9500 . ? C65 C66 1.368(14) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C70 F73 1.313(14) . ? C70 F72 1.324(14) . ? C70 F71 1.343(13) . ? C70 C74 1.468(13) . ? S71 N72 1.723(9) . ? S71 C71 1.745(10) . ? N71 C80 1.372(12) . ? N71 C72 1.433(11) . ? N71 H71 0.8800 . ? N72 C80 1.293(12) . ? C71 C72 1.385(13) . ? C71 C76 1.397(13) . ? C72 C73 1.382(13) . ? C73 C74 1.426(12) . ? C73 H73 0.9500 . ? C74 C75 1.381(13) . ? C75 C76 1.392(13) . ? C75 H75 0.9500 . ? C76 H76 0.9500 . ? C80 C81 1.485(12) . ? C81 C82 1.366(13) . ? C81 C86 1.412(13) . ? C82 C83 1.371(14) . ? C82 H82 0.9500 . ? C83 C84 1.383(15) . ? C83 H83 0.9500 . ? C84 C85 1.403(14) . ? C84 H84 0.9500 . ? C85 C86 1.373(13) . ? C85 H85 0.9500 . ? C86 H86 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 F12 C10 F13 108.3(12) . . ? F12 C10 F11 107.7(12) . . ? F13 C10 F11 104.4(11) . . ? F12 C10 C14 111.6(11) . . ? F13 C10 C14 113.0(10) . . ? F11 C10 C14 111.4(11) . . ? N12 S11 C11 103.3(5) . . ? C20 N11 C12 122.8(9) . . ? C20 N11 H11 118.6 . . ? C12 N11 H11 118.6 . . ? C20 N12 S11 117.2(9) . . ? C16 C11 C12 119.4(9) . . ? C16 C11 S11 123.6(8) . . ? C12 C11 S11 116.9(8) . . ? C13 C12 C11 119.2(9) . . ? C13 C12 N11 122.2(9) . . ? C11 C12 N11 118.5(9) . . ? C12 C13 C14 121.1(10) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 118.7(10) . . ? C15 C14 C10 120.6(10) . . ? C13 C14 C10 120.5(10) . . ? C16 C15 C14 119.9(11) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 121.3(10) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? N12 C20 N11 124.3(10) . . ? N12 C20 C21 118.1(10) . . ? N11 C20 C21 117.7(9) . . ? C22 C21 C26 117.9(10) . . ? C22 C21 C20 121.3(10) . . ? C26 C21 C20 120.7(10) . . ? C23 C22 C21 120.1(11) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 121.1(12) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 120.5(12) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 C24 119.2(12) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C25 C26 C21 121.2(11) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? F33 C30 F32 108.4(10) . . ? F33 C30 F31 105.1(11) . . ? F32 C30 F31 106.4(12) . . ? F33 C30 C34 112.2(11) . . ? F32 C30 C34 113.3(11) . . ? F31 C30 C34 111.0(10) . . ? N32 S31 C31 103.6(6) . . ? C40 N31 C32 122.8(10) . . ? C40 N31 H31 118.6 . . ? C32 N31 H31 118.6 . . ? C40 N32 S31 117.3(8) . . ? C32 C31 C36 119.7(9) . . ? C32 C31 S31 117.9(8) . . ? C36 C31 S31 122.4(9) . . ? C33 C32 C31 120.9(9) . . ? C33 C32 N31 120.9(10) . . ? C31 C32 N31 118.1(9) . . ? C32 C33 C34 119.5(10) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C35 C34 C33 118.9(10) . . ? C35 C34 C30 122.6(10) . . ? C33 C34 C30 118.1(10) . . ? C34 C35 C36 121.8(11) . . ? C34 C35 H35 119.1 . . ? C36 C35 H35 119.1 . . ? C35 C36 C31 118.8(11) . . ? C35 C36 H36 120.6 . . ? C31 C36 H36 120.6 . . ? N32 C40 N31 124.8(10) . . ? N32 C40 C41 118.4(9) . . ? N31 C40 C41 116.8(9) . . ? C42 C41 C46 119.4(10) . . ? C42 C41 C40 122.1(10) . . ? C46 C41 C40 118.4(10) . . ? C41 C42 C43 122.9(11) . . ? C41 C42 H42 118.6 . . ? C43 C42 H42 118.6 . . ? C44 C43 C42 117.8(13) . . ? C44 C43 H43 121.1 . . ? C42 C43 H43 121.1 . . ? C43 C44 C45 121.3(12) . . ? C43 C44 H44 119.4 . . ? C45 C44 H44 119.4 . . ? C46 C45 C44 120.9(12) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C45 C46 C41 117.7(11) . . ? C45 C46 H46 121.1 . . ? C41 C46 H46 121.1 . . ? F52 C50 F53 107.0(12) . . ? F52 C50 F51 105.9(11) . . ? F53 C50 F51 104.9(12) . . ? F52 C50 C54 113.9(11) . . ? F53 C50 C54 112.0(10) . . ? F51 C50 C54 112.5(11) . . ? N52 S51 C51 103.2(6) . . ? C60 N51 C52 123.0(10) . . ? C60 N51 H51 118.5 . . ? C52 N51 H51 118.5 . . ? C60 N52 S51 117.3(9) . . ? C56 C51 C52 118.2(9) . . ? C56 C51 S51 122.6(8) . . ? C52 C51 S51 119.1(8) . . ? C53 C52 C51 122.7(9) . . ? C53 C52 N51 119.4(9) . . ? C51 C52 N51 117.9(9) . . ? C52 C53 C54 117.4(10) . . ? C52 C53 H53 121.3 . . ? C54 C53 H53 121.3 . . ? C55 C54 C53 120.8(10) . . ? C55 C54 C50 120.5(10) . . ? C53 C54 C50 118.7(10) . . ? C56 C55 C54 119.7(11) . . ? C56 C55 H55 120.2 . . ? C54 C55 H55 120.2 . . ? C55 C56 C51 120.7(11) . . ? C55 C56 H56 119.6 . . ? C51 C56 H56 119.6 . . ? N52 C60 N51 125.6(10) . . ? N52 C60 C61 117.3(10) . . ? N51 C60 C61 117.0(9) . . ? C62 C61 C66 118.0(10) . . ? C62 C61 C60 122.6(10) . . ? C66 C61 C60 119.4(9) . . ? C63 C62 C61 122.3(11) . . ? C63 C62 H62 118.9 . . ? C61 C62 H62 118.9 . . ? C62 C63 C64 120.0(12) . . ? C62 C63 H63 120.0 . . ? C64 C63 H63 120.0 . . ? C63 C64 C65 119.0(12) . . ? C63 C64 H64 120.5 . . ? C65 C64 H64 120.5 . . ? C66 C65 C64 121.5(12) . . ? C66 C65 H65 119.2 . . ? C64 C65 H65 119.2 . . ? C65 C66 C61 119.1(11) . . ? C65 C66 H66 120.5 . . ? C61 C66 H66 120.5 . . ? F73 C70 F72 107.4(13) . . ? F73 C70 F71 104.7(11) . . ? F72 C70 F71 104.7(11) . . ? F73 C70 C74 114.9(10) . . ? F72 C70 C74 111.3(10) . . ? F71 C70 C74 113.1(11) . . ? N72 S71 C71 101.6(6) . . ? C80 N71 C72 120.6(10) . . ? C80 N71 H71 119.7 . . ? C72 N71 H71 119.7 . . ? C80 N72 S71 118.4(8) . . ? C72 C71 C76 119.9(9) . . ? C72 C71 S71 119.4(8) . . ? C76 C71 S71 120.5(9) . . ? C73 C72 C71 121.7(9) . . ? C73 C72 N71 118.7(10) . . ? C71 C72 N71 119.4(9) . . ? C72 C73 C74 117.4(10) . . ? C72 C73 H73 121.3 . . ? C74 C73 H73 121.3 . . ? C75 C74 C73 121.3(10) . . ? C75 C74 C70 122.0(10) . . ? C73 C74 C70 116.7(10) . . ? C74 C75 C76 119.6(11) . . ? C74 C75 H75 120.2 . . ? C76 C75 H75 120.2 . . ? C75 C76 C71 119.9(11) . . ? C75 C76 H76 120.1 . . ? C71 C76 H76 120.1 . . ? N72 C80 N71 126.3(10) . . ? N72 C80 C81 118.1(9) . . ? N71 C80 C81 115.6(9) . . ? C82 C81 C86 117.7(10) . . ? C82 C81 C80 124.2(10) . . ? C86 C81 C80 118.1(10) . . ? C81 C82 C83 121.8(11) . . ? C81 C82 H82 119.1 . . ? C83 C82 H82 119.1 . . ? C82 C83 C84 121.0(13) . . ? C82 C83 H83 119.5 . . ? C84 C83 H83 119.5 . . ? C83 C84 C85 118.3(12) . . ? C83 C84 H84 120.9 . . ? C85 C84 H84 120.9 . . ? C86 C85 C84 120.0(12) . . ? C86 C85 H85 120.0 . . ? C84 C85 H85 120.0 . . ? C85 C86 C81 121.0(11) . . ? C85 C86 H86 119.5 . . ? C81 C86 H86 119.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.796 _refine_diff_density_min -0.814 _refine_diff_density_rms 0.151 _database_code_depnum_ccdc_archive 'CCDC 969022'