# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_120705e_0m _database_code_depnum_ccdc_archive 'CCDC 892215' #TrackingRef '120705e_0m-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 N3 O S' _chemical_formula_sum 'C12 H11 N3 O S' _chemical_formula_weight 245.31 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 7.0809(7) _cell_length_b 7.6178(8) _cell_length_c 21.146(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1140.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512.0 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.886 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8566 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.85 _reflns_number_total 2255 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0384P)^2^+0.1287P] 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 1.04(9) _refine_ls_number_reflns 2255 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.61649(8) 0.94346(9) 0.21551(3) 0.04796(18) Uani 1 1 d . . . O1 O 1.3682(2) 0.9554(2) 0.36582(7) 0.0599(5) Uani 1 1 d . . . C2 C 1.1916(3) 0.8861(3) 0.35845(10) 0.0426(6) Uani 1 1 d . . . N3 N 0.8049(3) 0.8769(2) 0.11659(8) 0.0393(4) Uani 1 1 d . . . C7 C 1.1153(3) 0.9028(3) 0.29833(9) 0.0394(5) Uani 1 1 d . . . H7 H 1.1863 0.9548 0.2664 0.047 Uiso 1 1 calc R . . C8 C 0.8524(3) 0.8668(3) 0.22142(10) 0.0362(5) Uani 1 1 d . . . C12 C 0.9324(3) 0.8380(3) 0.16459(10) 0.0357(5) Uani 1 1 d . . . C11 C 0.6334(3) 0.9347(3) 0.13418(9) 0.0428(5) Uani 1 1 d . . . C10 C 0.6452(3) 0.9242(3) 0.03658(10) 0.0548(7) Uani 1 1 d . . . H10 H 0.6086 0.9328 -0.0056 0.066 Uiso 1 1 calc R . . C6 C 0.9349(3) 0.8431(3) 0.28532(10) 0.0373(5) Uani 1 1 d . . . N2 N 0.5249(3) 0.9686(3) 0.08431(9) 0.0541(5) Uani 1 1 d . . . C4 C 0.9062(4) 0.7477(3) 0.39293(10) 0.0493(6) Uani 1 1 d . . . H4 H 0.8358 0.6948 0.4248 0.059 Uiso 1 1 calc R . . N1 N 0.8160(3) 0.8684(3) 0.05233(8) 0.0495(5) Uani 1 1 d . . . C3 C 1.0866(4) 0.8063(3) 0.40609(10) 0.0479(6) Uani 1 1 d . . . H3 H 1.1373 0.7926 0.4464 0.057 Uiso 1 1 calc R . . C9 C 1.1215(3) 0.7696(3) 0.14760(10) 0.0450(5) Uani 1 1 d . . . H9A H 1.1895 0.7401 0.1854 0.067 Uiso 1 1 calc R . . H9B H 1.1899 0.8576 0.1246 0.067 Uiso 1 1 calc R . . H9C H 1.1077 0.6667 0.1218 0.067 Uiso 1 1 calc R . . C5 C 0.8285(3) 0.7661(3) 0.33360(10) 0.0442(6) Uani 1 1 d . . . H5 H 0.7061 0.7276 0.3257 0.053 Uiso 1 1 calc R . . C1 C 1.4458(4) 0.9624(4) 0.42789(12) 0.0660(8) Uani 1 1 d . . . H1A H 1.3599 1.0228 0.4555 0.099 Uiso 1 1 calc R . . H1B H 1.5641 1.0239 0.4268 0.099 Uiso 1 1 calc R . . H1C H 1.4657 0.8452 0.4432 0.099 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 0.0366(3) 0.0654(4) 0.0418(3) -0.0032(3) 0.0053(3) 0.0061(3) O1 0.0435(10) 0.0876(13) 0.0486(9) 0.0006(9) -0.0088(8) -0.0054(11) C2 0.0391(13) 0.0452(14) 0.0435(12) -0.0041(10) -0.0003(10) 0.0044(11) N3 0.0354(10) 0.0468(11) 0.0357(9) 0.0015(8) 0.0014(8) -0.0062(9) C7 0.0398(12) 0.0411(12) 0.0372(10) 0.0014(9) 0.0054(10) 0.0028(11) C8 0.0329(11) 0.0380(11) 0.0378(11) -0.0012(9) 0.0040(10) -0.0026(9) C12 0.0331(12) 0.0356(11) 0.0384(11) -0.0001(9) 0.0018(9) -0.0055(9) C11 0.0355(12) 0.0500(13) 0.0431(12) 0.0003(11) 0.0012(10) -0.0034(12) C10 0.0557(16) 0.0695(17) 0.0392(12) 0.0041(12) -0.0071(11) -0.0064(15) C6 0.0417(12) 0.0334(11) 0.0369(11) -0.0039(10) 0.0027(10) 0.0024(9) N2 0.0427(11) 0.0726(15) 0.0470(11) 0.0028(11) -0.0046(9) 0.0008(11) C4 0.0567(15) 0.0513(14) 0.0400(12) 0.0057(10) 0.0101(12) -0.0004(13) N1 0.0523(13) 0.0626(14) 0.0336(10) -0.0009(9) 0.0029(9) -0.0043(11) C3 0.0573(16) 0.0492(14) 0.0371(11) 0.0029(10) -0.0012(11) 0.0112(12) C9 0.0393(13) 0.0518(14) 0.0438(11) -0.0021(10) 0.0053(11) -0.0002(12) C5 0.0427(14) 0.0475(14) 0.0425(12) 0.0001(10) 0.0066(10) -0.0037(11) C1 0.0586(16) 0.081(2) 0.0584(16) -0.0074(15) -0.0179(13) 0.0040(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 S1 C11 1.725(2) . ? S1 C8 1.774(2) . ? O1 C2 1.366(3) . ? O1 C1 1.424(3) . ? C2 C7 1.387(3) . ? C2 C3 1.392(3) . ? N3 C11 1.344(3) . ? N3 N1 1.363(2) . ? N3 C12 1.391(3) . ? C7 C6 1.384(3) . ? C7 H7 0.9300 . ? C8 C12 1.346(3) . ? C8 C6 1.483(3) . ? C12 C9 1.481(3) . ? C11 N2 1.330(3) . ? C10 N1 1.324(3) . ? C10 N2 1.364(3) . ? C10 H10 0.9300 . ? C6 C5 1.398(3) . ? C4 C5 1.377(3) . ? C4 C3 1.382(3) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C5 H5 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 S1 C8 89.54(10) . . ? C2 O1 C1 118.21(19) . . ? O1 C2 C7 115.2(2) . . ? O1 C2 C3 125.1(2) . . ? C7 C2 C3 119.7(2) . . ? C11 N3 N1 110.11(18) . . ? C11 N3 C12 117.02(17) . . ? N1 N3 C12 132.86(19) . . ? C6 C7 C2 120.7(2) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C12 C8 C6 128.87(19) . . ? C12 C8 S1 112.76(16) . . ? C6 C8 S1 118.36(15) . . ? C8 C12 N3 110.09(18) . . ? C8 C12 C9 130.9(2) . . ? N3 C12 C9 119.01(18) . . ? N2 C11 N3 111.48(19) . . ? N2 C11 S1 137.95(18) . . ? N3 C11 S1 110.57(15) . . ? N1 C10 N2 117.6(2) . . ? N1 C10 H10 121.2 . . ? N2 C10 H10 121.2 . . ? C7 C6 C5 119.4(2) . . ? C7 C6 C8 120.29(18) . . ? C5 C6 C8 120.29(19) . . ? C11 N2 C10 100.23(19) . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C10 N1 N3 100.53(18) . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C12 C9 H9A 109.5 . . ? C12 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C12 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 26.85 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.129 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.037 data_1 _database_code_depnum_ccdc_archive 'CCDC 894296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 Br Cl0 N3 S' _chemical_formula_weight 356.24 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3583(10) _cell_length_b 11.9472(18) _cell_length_c 19.211(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.318(2) _cell_angle_gamma 90.00 _cell_volume 1458.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 2.956 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5253 _exptl_absorpt_correction_T_max 0.6182 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10605 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2803 _reflns_number_gt 2114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.2272P] 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 2803 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.39435(5) 0.21681(3) 0.067017(18) 0.05241(14) Uani 1 1 d . . . C1 C 0.1135(5) 0.8709(3) 0.02804(19) 0.0622(10) Uani 1 1 d . . . H1 H -0.0032 0.8838 -0.0010 0.075 Uiso 1 1 calc R . . C2 C 0.3758(5) 0.9021(3) 0.09030(17) 0.0490(8) Uani 1 1 d . . . C3 C 0.4902(5) 0.7223(2) 0.12218(16) 0.0412(7) Uani 1 1 d . . . C4 C 0.6363(5) 0.7868(2) 0.15622(16) 0.0429(7) Uani 1 1 d . . . C5 C 0.8076(5) 0.7539(3) 0.20391(16) 0.0410(7) Uani 1 1 d . . . C6 C 0.9896(5) 0.8194(3) 0.20955(17) 0.0524(8) Uani 1 1 d . . . H6 H 1.0044 0.8814 0.1808 0.063 Uiso 1 1 calc R . . C7 C 1.1487(6) 0.7929(3) 0.2576(2) 0.0637(10) Uani 1 1 d . . . H7 H 1.2691 0.8370 0.2607 0.076 Uiso 1 1 calc R . . C8 C 1.1287(6) 0.7020(3) 0.3004(2) 0.0674(11) Uani 1 1 d . . . H8 H 1.2353 0.6839 0.3323 0.081 Uiso 1 1 calc R . . C9 C 0.9494(6) 0.6380(3) 0.29560(19) 0.0658(10) Uani 1 1 d . . . H9 H 0.9355 0.5765 0.3248 0.079 Uiso 1 1 calc R . . C10 C 0.7887(5) 0.6632(3) 0.24813(17) 0.0526(8) Uani 1 1 d . . . H10 H 0.6681 0.6192 0.2460 0.063 Uiso 1 1 calc R . . C11 C 0.4751(4) 0.5989(3) 0.11446(15) 0.0417(7) Uani 1 1 d . . . C12 C 0.6413(5) 0.5386(2) 0.08828(16) 0.0440(7) Uani 1 1 d . . . H12 H 0.7672 0.5748 0.0791 0.053 Uiso 1 1 calc R . . C13 C 0.6223(5) 0.4250(2) 0.07556(16) 0.0461(7) Uani 1 1 d . . . H13 H 0.7337 0.3843 0.0579 0.055 Uiso 1 1 calc R . . C14 C 0.4341(5) 0.3737(3) 0.08977(16) 0.0439(7) Uani 1 1 d . . . C15 C 0.2687(5) 0.4303(3) 0.11771(18) 0.0561(9) Uani 1 1 d . . . H15 H 0.1457 0.3929 0.1287 0.067 Uiso 1 1 calc R . . C16 C 0.2883(5) 0.5445(3) 0.12924(18) 0.0548(9) Uani 1 1 d . . . H16 H 0.1761 0.5846 0.1469 0.066 Uiso 1 1 calc R . . N1 N 0.1704(4) 0.7679(2) 0.04609(15) 0.0549(7) Uani 1 1 d . . . N2 N 0.2324(5) 0.9572(2) 0.05358(16) 0.0618(8) Uani 1 1 d . . . N3 N 0.3434(4) 0.7904(2) 0.08719(14) 0.0453(6) Uani 1 1 d . . . S1 S 0.59334(13) 0.93159(7) 0.14201(5) 0.0545(2) 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 Br1 0.0655(3) 0.0299(2) 0.0613(2) -0.00309(14) -0.01092(16) -0.00473(15) C1 0.060(2) 0.051(2) 0.075(2) -0.0053(19) -0.0264(19) 0.0126(19) C2 0.0504(19) 0.0345(18) 0.061(2) -0.0024(15) -0.0144(16) 0.0061(14) C3 0.0396(16) 0.0330(17) 0.0507(17) -0.0007(14) -0.0054(14) 0.0035(13) C4 0.0454(18) 0.0324(17) 0.0506(17) -0.0005(13) -0.0051(14) 0.0018(14) C5 0.0441(17) 0.0342(16) 0.0445(16) -0.0033(13) -0.0036(14) 0.0023(13) C6 0.0470(19) 0.049(2) 0.061(2) 0.0025(16) -0.0057(16) 0.0013(16) C7 0.047(2) 0.068(3) 0.076(3) -0.011(2) -0.0124(18) 0.0003(18) C8 0.070(3) 0.063(3) 0.068(2) -0.006(2) -0.027(2) 0.016(2) C9 0.084(3) 0.049(2) 0.064(2) 0.0103(18) -0.018(2) 0.012(2) C10 0.059(2) 0.0383(19) 0.059(2) 0.0038(16) -0.0088(17) 0.0006(16) C11 0.0425(17) 0.0344(17) 0.0479(17) -0.0038(14) -0.0070(14) 0.0001(13) C12 0.0396(17) 0.0345(17) 0.0575(19) -0.0019(14) -0.0051(14) -0.0028(13) C13 0.0460(18) 0.0354(17) 0.0566(19) -0.0074(14) -0.0069(15) 0.0042(14) C14 0.0527(18) 0.0294(16) 0.0491(17) -0.0039(13) -0.0101(14) -0.0011(14) C15 0.053(2) 0.041(2) 0.074(2) -0.0039(17) 0.0064(18) -0.0079(16) C16 0.0476(19) 0.041(2) 0.076(2) -0.0082(17) 0.0082(17) 0.0008(15) N1 0.0525(17) 0.0442(17) 0.0669(18) -0.0087(14) -0.0222(14) 0.0074(13) N2 0.0665(19) 0.0410(16) 0.077(2) -0.0043(15) -0.0241(16) 0.0116(15) N3 0.0440(14) 0.0351(15) 0.0562(15) -0.0051(12) -0.0143(12) 0.0061(11) S1 0.0594(5) 0.0298(4) 0.0732(6) -0.0011(4) -0.0208(4) -0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.940(3) . ? C1 N1 1.326(4) . ? C1 N2 1.363(4) . ? C1 H1 0.9300 . ? C2 N2 1.317(4) . ? C2 N3 1.351(4) . ? C2 S1 1.721(3) . ? C3 C4 1.362(4) . ? C3 N3 1.399(4) . ? C3 C11 1.485(4) . ? C4 C5 1.461(4) . ? C4 S1 1.772(3) . ? C5 C10 1.383(4) . ? C5 C6 1.400(4) . ? C6 C7 1.390(5) . ? C6 H6 0.9300 . ? C7 C8 1.368(5) . ? C7 H7 0.9300 . ? C8 C9 1.374(5) . ? C8 H8 0.9300 . ? C9 C10 1.387(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.383(4) . ? C11 C16 1.389(4) . ? C12 C13 1.384(4) . ? C12 H12 0.9300 . ? C13 C14 1.377(4) . ? C13 H13 0.9300 . ? C14 C15 1.370(4) . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N1 N3 1.366(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 117.5(3) . . ? N1 C1 H1 121.2 . . ? N2 C1 H1 121.2 . . ? N2 C2 N3 111.5(3) . . ? N2 C2 S1 138.1(3) . . ? N3 C2 S1 110.3(2) . . ? C4 C3 N3 110.0(3) . . ? C4 C3 C11 130.6(3) . . ? N3 C3 C11 119.3(3) . . ? C3 C4 C5 129.7(3) . . ? C3 C4 S1 112.2(2) . . ? C5 C4 S1 118.0(2) . . ? C10 C5 C6 118.3(3) . . ? C10 C5 C4 121.5(3) . . ? C6 C5 C4 120.1(3) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 120.2(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.4(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 121.3(3) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C5 C10 C9 120.1(3) . . ? C5 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C16 119.6(3) . . ? C12 C11 C3 120.3(3) . . ? C16 C11 C3 119.9(3) . . ? C11 C12 C13 120.7(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 118.3(3) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C15 C14 C13 122.5(3) . . ? C15 C14 Br1 117.9(2) . . ? C13 C14 Br1 119.6(2) . . ? C14 C15 C16 118.8(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C15 C16 C11 120.1(3) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C1 N1 N3 100.3(3) . . ? C2 N2 C1 100.7(3) . . ? C2 N3 N1 109.9(2) . . ? C2 N3 C3 117.0(3) . . ? N1 N3 C3 133.1(3) . . ? C2 S1 C4 90.45(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C3 C4 C5 174.2(3) . . . . ? C11 C3 C4 C5 -9.7(6) . . . . ? N3 C3 C4 S1 -1.8(3) . . . . ? C11 C3 C4 S1 174.3(3) . . . . ? C3 C4 C5 C10 -33.2(5) . . . . ? S1 C4 C5 C10 142.7(3) . . . . ? C3 C4 C5 C6 151.8(3) . . . . ? S1 C4 C5 C6 -32.4(4) . . . . ? C10 C5 C6 C7 1.0(5) . . . . ? C4 C5 C6 C7 176.2(3) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C6 C7 C8 C9 -0.5(6) . . . . ? C7 C8 C9 C10 0.3(6) . . . . ? C6 C5 C10 C9 -1.2(5) . . . . ? C4 C5 C10 C9 -176.3(3) . . . . ? C8 C9 C10 C5 0.6(5) . . . . ? C4 C3 C11 C12 -54.7(5) . . . . ? N3 C3 C11 C12 121.1(3) . . . . ? C4 C3 C11 C16 129.5(4) . . . . ? N3 C3 C11 C16 -54.7(4) . . . . ? C16 C11 C12 C13 1.1(5) . . . . ? C3 C11 C12 C13 -174.7(3) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C12 C13 C14 C15 -1.9(5) . . . . ? C12 C13 C14 Br1 176.0(2) . . . . ? C13 C14 C15 C16 2.9(5) . . . . ? Br1 C14 C15 C16 -175.0(3) . . . . ? C14 C15 C16 C11 -1.9(5) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C3 C11 C16 C15 175.7(3) . . . . ? N2 C1 N1 N3 -0.2(4) . . . . ? N3 C2 N2 C1 -0.4(4) . . . . ? S1 C2 N2 C1 -179.8(3) . . . . ? N1 C1 N2 C2 0.4(4) . . . . ? N2 C2 N3 N1 0.4(4) . . . . ? S1 C2 N3 N1 180.0(2) . . . . ? N2 C2 N3 C3 177.8(3) . . . . ? S1 C2 N3 C3 -2.6(4) . . . . ? C1 N1 N3 C2 -0.1(4) . . . . ? C1 N1 N3 C3 -177.0(3) . . . . ? C4 C3 N3 C2 2.9(4) . . . . ? C11 C3 N3 C2 -173.7(3) . . . . ? C4 C3 N3 N1 179.6(3) . . . . ? C11 C3 N3 N1 3.0(5) . . . . ? N2 C2 S1 C4 -179.3(4) . . . . ? N3 C2 S1 C4 1.2(3) . . . . ? C3 C4 S1 C2 0.4(3) . . . . ? C5 C4 S1 C2 -176.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.646 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.074