# Electronic Supplementary Material (ESI) for CrystEngComm # 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_1 _database_code_depnum_ccdc_archive 'CCDC 919699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H4 N2 S' _chemical_formula_weight 112.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 4.1280(4) _cell_length_b 29.664(3) _cell_length_c 8.0200(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.296(9) _cell_angle_gamma 90.00 _cell_volume 963.05(16) _cell_formula_units_Z 8 _cell_measurement_temperature 130(1) _cell_measurement_reflns_used 2835 _cell_measurement_theta_min 2.9769 _cell_measurement_theta_max 76.0808 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 4.717 _exptl_absorpt_correction_T_min 0.48682 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ; _diffrn_ambient_temperature 130(1) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 5463 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 70.00 _reflns_number_total 1805 _reflns_number_gt 1630 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1021P)^2^+2.6565P] 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 1805 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.2028 _refine_ls_wR_factor_gt 0.2012 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 N1A N 0.6951(8) 0.14651(11) 0.1561(4) 0.0235(7) Uani 1 1 d . . . C2A C 0.5629(9) 0.12257(14) 0.2727(4) 0.0200(8) Uani 1 1 d . . . S2A S 0.5276(2) 0.06615(3) 0.26488(11) 0.0256(4) Uani 1 1 d . . . N3A N 0.4578(8) 0.14676(11) 0.3989(4) 0.0213(7) Uani 1 1 d . . . H3A H 0.381(14) 0.1314(18) 0.480(7) 0.054(16) Uiso 1 1 d . . . C4A C 0.4751(10) 0.19147(14) 0.4107(5) 0.0237(8) Uani 1 1 d . . . H4A H 0.412(11) 0.2024(15) 0.498(6) 0.027(12) Uiso 1 1 d . . . C5A C 0.6006(10) 0.21606(14) 0.2931(5) 0.0250(9) Uani 1 1 d . . . H5A H 0.610(9) 0.2463(16) 0.298(5) 0.016(10) Uiso 1 1 d . . . C6A C 0.7073(10) 0.19077(14) 0.1663(5) 0.0243(9) Uani 1 1 d . . . H6A H 0.807(11) 0.2056(15) 0.085(6) 0.029(12) Uiso 1 1 d . . . N1B N 0.1592(8) 0.10285(11) 0.6436(4) 0.0226(7) Uani 1 1 d . . . C2B C 0.0603(9) 0.12732(14) 0.7701(4) 0.0217(8) Uani 1 1 d . . . S2B S 0.0959(3) 0.18362(3) 0.78224(12) 0.0240(4) Uani 1 1 d . . . N3B N -0.0749(8) 0.10368(11) 0.8879(4) 0.0217(7) Uani 1 1 d . . . H3B H -0.140(16) 0.120(2) 0.975(8) 0.067(18) Uiso 1 1 d . . . C4B C -0.1103(10) 0.05895(14) 0.8839(5) 0.0243(9) Uani 1 1 d . . . H4B H -0.204(12) 0.0469(16) 0.966(6) 0.036(13) Uiso 1 1 d . . . C5B C -0.0138(10) 0.03385(14) 0.7575(5) 0.0249(9) Uani 1 1 d . . . H5B H -0.031(11) 0.0027(18) 0.754(6) 0.030 Uiso 1 1 d . . . C6B C 0.1219(10) 0.05871(14) 0.6389(5) 0.0244(9) Uani 1 1 d . . . H6B H 0.189(11) 0.0435(15) 0.548(6) 0.025(11) 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 N1A 0.0256(17) 0.0311(17) 0.0161(16) 0.0017(12) 0.0093(13) 0.0018(13) C2A 0.0115(17) 0.039(2) 0.0084(17) 0.0002(13) -0.0010(13) 0.0021(14) S2A 0.0319(6) 0.0284(6) 0.0193(6) -0.0008(3) 0.0120(4) -0.0009(4) N3A 0.0237(17) 0.0305(17) 0.0115(15) 0.0009(12) 0.0077(13) -0.0005(13) C4A 0.025(2) 0.035(2) 0.0127(18) -0.0015(15) 0.0064(16) 0.0024(16) C5A 0.030(2) 0.027(2) 0.0193(19) 0.0002(14) 0.0079(17) 0.0002(16) C6A 0.023(2) 0.033(2) 0.0163(19) 0.0048(15) 0.0045(16) 0.0010(16) N1B 0.0230(17) 0.0325(17) 0.0134(15) -0.0010(12) 0.0066(13) 0.0002(13) C2B 0.0176(18) 0.035(2) 0.0120(17) -0.0007(14) 0.0031(14) -0.0008(15) S2B 0.0289(6) 0.0274(6) 0.0179(6) -0.0009(3) 0.0098(4) -0.0010(4) N3B 0.0225(17) 0.0323(17) 0.0116(15) -0.0002(12) 0.0063(13) 0.0005(13) C4B 0.025(2) 0.034(2) 0.0151(18) 0.0036(15) 0.0084(16) 0.0003(16) C5B 0.029(2) 0.029(2) 0.0170(19) 0.0013(15) 0.0058(16) -0.0002(16) C6B 0.026(2) 0.034(2) 0.0155(18) -0.0025(15) 0.0070(16) 0.0010(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1A C6A 1.316(5) . ? N1A C2A 1.370(5) . ? C2A N3A 1.378(5) . ? C2A S2A 1.680(4) . ? N3A C4A 1.331(5) . ? N3A H3A 0.90(6) . ? C4A C5A 1.371(5) . ? C4A H4A 0.86(5) . ? C5A C6A 1.403(5) . ? C5A H5A 0.90(5) . ? C6A H6A 0.95(5) . ? N1B C6B 1.318(5) . ? N1B C2B 1.373(5) . ? C2B N3B 1.379(5) . ? C2B S2B 1.678(4) . ? N3B C4B 1.335(5) . ? N3B H3B 0.93(6) . ? C4B C5B 1.378(5) . ? C4B H4B 0.90(5) . ? C5B C6B 1.404(5) . ? C5B H5B 0.93(5) . ? C6B H6B 0.95(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 C6A N1A C2A 119.4(3) . . ? N1A C2A N3A 117.1(4) . . ? N1A C2A S2A 122.3(3) . . ? N3A C2A S2A 120.6(3) . . ? C4A N3A C2A 123.4(3) . . ? C4A N3A H3A 118(3) . . ? C2A N3A H3A 118(3) . . ? N3A C4A C5A 120.2(4) . . ? N3A C4A H4A 115(3) . . ? C5A C4A H4A 125(3) . . ? C4A C5A C6A 115.4(4) . . ? C4A C5A H5A 121(2) . . ? C6A C5A H5A 123(2) . . ? N1A C6A C5A 124.4(4) . . ? N1A C6A H6A 116(3) . . ? C5A C6A H6A 120(3) . . ? C6B N1B C2B 119.8(3) . . ? N1B C2B N3B 117.1(4) . . ? N1B C2B S2B 122.3(3) . . ? N3B C2B S2B 120.6(3) . . ? C4B N3B C2B 123.1(3) . . ? C4B N3B H3B 119(4) . . ? C2B N3B H3B 118(4) . . ? N3B C4B C5B 120.6(4) . . ? N3B C4B H4B 116(3) . . ? C5B C4B H4B 123(3) . . ? C4B C5B C6B 115.2(4) . . ? C4B C5B H5B 122(3) . . ? C6B C5B H5B 123(3) . . ? N1B C6B C5B 124.2(4) . . ? N1B C6B H6B 117(3) . . ? C5B C6B H6B 119(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3A H3A N1B 0.90(6) 1.94(6) 2.831(5) 172(5) . C4A H4A S2B 0.86(5) 2.89(5) 3.635(4) 146(4) . N3B H3B N1A 0.93(6) 1.89(6) 2.818(5) 173(5) 1_456 C4B H4B S2A 0.90(5) 2.89(5) 3.661(4) 145(4) 1_456 C5A H5A S2B 0.90(5) 2.91(4) 3.621(4) 137(3) 4_665 C5A H5A S2B 0.90(5) 2.96(4) 3.624(4) 132(3) 4_565 C6A H6A S2B 0.95(5) 2.98(5) 3.747(4) 139(3) 1_654 C5B H5B S2A 0.93(5) 2.88(5) 3.631(4) 139(4) 3_556 C5B H5B S2A 0.93(5) 2.94(5) 3.606(4) 130(3) 3_656 C6B H6B S2A 0.95(4) 2.97(4) 3.717(4) 137(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.774 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.109 data_2 _database_code_depnum_ccdc_archive 'CCDC 919700' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N2 S, Cl' _chemical_formula_sum 'C4 H5 Cl N2 S' _chemical_formula_weight 148.61 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z-1/2' '-x, y, z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.0166(10) _cell_length_b 12.9113(9) _cell_length_c 6.5423(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 677.16(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1301 _cell_measurement_theta_min 3.2412 _cell_measurement_theta_max 23.60 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.767 _exptl_absorpt_correction_T_min 0.91682 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 730 _diffrn_reflns_av_R_equivalents 0.0123 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.53 _reflns_number_total 382 _reflns_number_gt 338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0323P)^2^+0.7012P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 382 _refine_ls_number_parameters 38 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 Cl Cl 0.5000 0.20574(9) 0.2500 0.0537(5) Uani 1 4 d S . . S1 S 0.5000 0.40962(10) 0.7500 0.0919(7) Uani 1 4 d S . . N2 N 0.6416(4) 0.2246(2) 0.7500 0.0480(7) Uani 1 2 d S . . C1 C 0.5000 0.2829(3) 0.7500 0.0478(11) Uani 1 4 d S . . C4 C 0.5000 0.0666(4) 0.7500 0.0640(15) Uani 1 4 d S . . C3A C 0.6462(5) 0.1220(3) 0.7500 0.0563(9) Uani 1 2 d S . . H2 H 0.727(5) 0.253(3) 0.7500 0.056(11) Uiso 1 2 d S . . H4 H 0.5000 0.000(6) 0.7500 0.09(2) Uiso 1 4 d S . . H3A H 0.783(5) 0.093(2) 0.7500 0.077(12) Uiso 1 2 d S . . 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 Cl 0.0431(6) 0.0615(8) 0.0565(8) 0.000 0.000 0.000 S1 0.0756(10) 0.0370(7) 0.1630(19) 0.000 0.000 0.000 N2 0.0407(15) 0.0500(16) 0.0532(17) 0.000 0.000 -0.0008(13) C1 0.047(2) 0.043(2) 0.053(3) 0.000 0.000 0.000 C4 0.097(4) 0.036(2) 0.059(3) 0.000 0.000 0.000 C3A 0.068(2) 0.0501(18) 0.051(2) 0.000 0.000 0.0142(18) _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 C1 1.636(4) . ? N2 C3A 1.326(4) . ? N2 C1 1.361(3) . ? C1 N2 1.361(3) 11_655 ? C4 C3A 1.373(5) . ? C4 C3A 1.373(5) 11_655 ? 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 C3A N2 C1 125.1(3) . . ? N2 C1 N2 112.9(4) 11_655 . ? N2 C1 S1 123.5(2) 11_655 . ? N2 C1 S1 123.5(2) . . ? C3A C4 C3A 117.2(4) . 11_655 ? N2 C3A C4 119.8(4) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.236 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.046 data_3 _database_code_depnum_ccdc_archive 'CCDC 919701' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N2 S, Br' _chemical_formula_sum 'C4 H5 Br N2 S' _chemical_formula_weight 193.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 14.0264(6) _cell_length_b 4.6351(2) _cell_length_c 10.5403(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 685.26(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6389 _cell_measurement_theta_min 3.1481 _cell_measurement_theta_max 76.0947 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.871 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 10.203 _exptl_absorpt_correction_T_min 0.34421 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET) (compiled Oct 21 2010,17:48:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 7308 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.31 _diffrn_reflns_theta_max 76.28 _reflns_number_total 1406 _reflns_number_gt 1380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0576P)^2^+0.4285P] 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 refall _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(5) _refine_ls_number_reflns 1406 _refine_ls_number_parameters 93 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.002 _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 0.7494(3) 0.9115(10) 0.4438(4) 0.0614(10) Uani 1 1 d . . . H1 H 0.804(6) 0.859(13) 0.415(6) 0.066(18) Uiso 1 1 d . . . C2 C 0.7460(4) 1.1046(9) 0.5394(8) 0.0539(10) Uani 1 1 d . . . S2 S 0.84329(8) 1.2264(4) 0.61358(17) 0.0696(3) Uani 1 1 d . . . N3 N 0.6561(3) 1.1889(10) 0.5734(4) 0.0537(9) Uani 1 1 d . . . H3 H 0.653(3) 1.329(11) 0.644(5) 0.043(12) Uiso 1 1 d . . . C4 C 0.5777(3) 1.0796(13) 0.5203(6) 0.0610(12) Uani 1 1 d . . . H4 H 0.519(6) 1.148(12) 0.555(7) 0.069(18) Uiso 1 1 d . . . C5 C 0.5829(4) 0.8815(13) 0.4250(6) 0.0673(15) Uani 1 1 d . . . H5 H 0.533(6) 0.797(14) 0.373(7) 0.08(2) Uiso 1 1 d . . . C6 C 0.6717(5) 0.8021(14) 0.3859(5) 0.0655(13) Uani 1 1 d . . . H6 H 0.687(5) 0.669(12) 0.319(6) 0.062(17) Uiso 1 1 d . . . Br1 Br 0.91672(3) 0.63322(10) 0.27922(7) 0.06197(18) 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 N1 0.052(2) 0.078(3) 0.054(2) -0.0077(19) -0.0025(18) 0.0155(19) C2 0.048(2) 0.060(2) 0.054(3) 0.011(2) -0.0005(17) 0.001(2) S2 0.0482(5) 0.0915(9) 0.0690(7) -0.0112(7) -0.0029(6) -0.0044(6) N3 0.051(2) 0.057(2) 0.053(2) -0.0020(16) 0.0003(15) -0.0012(16) C4 0.051(3) 0.067(3) 0.065(3) 0.004(3) -0.005(2) -0.0006(19) C5 0.067(3) 0.073(4) 0.062(3) -0.002(3) -0.014(2) -0.001(2) C6 0.079(4) 0.063(3) 0.055(3) -0.004(2) -0.010(2) 0.006(3) Br1 0.0580(3) 0.0687(3) 0.0592(3) -0.0091(3) -0.0048(3) 0.00681(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.348(9) . ? N1 C6 1.349(8) . ? N1 H1 0.85(8) . ? C2 N3 1.368(7) . ? C2 S2 1.671(7) . ? N3 C4 1.333(7) . ? N3 H3 0.99(5) . ? C4 C5 1.363(9) . ? C4 H4 0.96(8) . ? C5 C6 1.362(9) . ? C5 H5 0.97(8) . ? C6 H6 0.97(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 124.0(5) . . ? C2 N1 H1 119(5) . . ? C6 N1 H1 117(5) . . ? N1 C2 N3 114.7(5) . . ? N1 C2 S2 123.0(4) . . ? N3 C2 S2 122.3(5) . . ? C4 N3 C2 122.8(5) . . ? C4 N3 H3 122(3) . . ? C2 N3 H3 115(3) . . ? N3 C4 C5 121.4(5) . . ? N3 C4 H4 115(4) . . ? C5 C4 H4 123(4) . . ? C6 C5 C4 117.0(5) . . ? C6 C5 H5 112(5) . . ? C4 C5 H5 131(5) . . ? N1 C6 C5 120.1(5) . . ? N1 C6 H6 113(4) . . ? C5 C6 H6 127(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.85(8) 2.38(8) 3.191(4) 159(6) . N3 H3 Br1 0.99(5) 2.23(5) 3.161(4) 156(4) 3_665 C5 H5 Br1 0.97(8) 2.76(8) 3.672(6) 157(5) 4_465 C6 H6 S2 0.97(6) 3.01(6) 3.925(6) 159(5) 3_644 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.535 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.072 data_4 _database_code_depnum_ccdc_archive 'CCDC 919702' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N2 S, Br' _chemical_formula_sum 'C4 H5 Br N2 S' _chemical_formula_weight 193.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5502(3) _cell_length_b 8.6872(4) _cell_length_c 13.6237(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1366.99(8) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7229 _cell_measurement_theta_min 3.2412 _cell_measurement_theta_max 73.5979 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.876 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 10.229 _exptl_absorpt_correction_T_min 0.53460 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET) (compiled Oct 21 2010,17:48:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 9789 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.50 _diffrn_reflns_theta_max 73.76 _reflns_number_total 1381 _reflns_number_gt 1311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0333P)^2^+0.7757P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1381 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.41879(15) 0.3335(2) 0.48344(14) 0.0452(4) Uani 1 1 d . . . H1 H 0.393(3) 0.389(4) 0.531(2) 0.067(9) Uiso 1 1 d . . . C2 C 0.51199(17) 0.2405(2) 0.50130(15) 0.0401(4) Uani 1 1 d . . . S2 S 0.57945(6) 0.23378(9) 0.60777(4) 0.05770(18) Uani 1 1 d . . . N3 N 0.54302(16) 0.1534(2) 0.42200(13) 0.0423(4) Uani 1 1 d . . . H3 H 0.608(3) 0.097(4) 0.426(2) 0.061(8) Uiso 1 1 d . . . C4 C 0.4878(2) 0.1548(3) 0.33625(17) 0.0481(5) Uani 1 1 d . . . H4 H 0.521(2) 0.086(3) 0.290(2) 0.058(8) Uiso 1 1 d . . . C5 C 0.3949(2) 0.2495(3) 0.32094(19) 0.0556(6) Uani 1 1 d . . . H5 H 0.354(3) 0.251(4) 0.259(2) 0.069(8) Uiso 1 1 d . . . C6 C 0.3629(2) 0.3414(3) 0.39820(19) 0.0508(5) Uani 1 1 d . . . H6 H 0.296(3) 0.417(4) 0.396(2) 0.060(8) Uiso 1 1 d . . . Br1 Br 0.27149(2) 0.54487(3) 0.62947(2) 0.05538(13) 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 N1 0.0395(9) 0.0476(10) 0.0484(10) -0.0073(8) 0.0076(7) 0.0019(8) C2 0.0377(9) 0.0416(10) 0.0411(10) -0.0009(9) 0.0063(8) -0.0039(9) S2 0.0551(3) 0.0761(4) 0.0419(3) -0.0063(3) -0.0033(2) 0.0038(3) N3 0.0430(9) 0.0423(9) 0.0417(9) 0.0002(7) 0.0038(7) 0.0048(8) C4 0.0563(13) 0.0497(12) 0.0385(10) -0.0011(9) 0.0041(9) 0.0021(10) C5 0.0532(13) 0.0674(15) 0.0461(12) 0.0023(11) -0.0056(10) 0.0036(12) C6 0.0397(11) 0.0530(12) 0.0596(13) 0.0048(11) 0.0004(10) 0.0033(10) Br1 0.04974(19) 0.04711(17) 0.0693(2) -0.01766(11) 0.01790(11) -0.00874(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.330(3) . ? N1 C2 1.367(3) . ? N1 H1 0.87(3) . ? C2 N3 1.367(3) . ? C2 S2 1.648(2) . ? N3 C4 1.331(3) . ? N3 H3 0.90(3) . ? C4 C5 1.369(4) . ? C4 H4 0.95(3) . ? C5 C6 1.372(4) . ? C5 H5 0.97(3) . ? C6 H6 1.02(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 C6 N1 C2 124.6(2) . . ? C6 N1 H1 118(2) . . ? C2 N1 H1 118(2) . . ? N1 C2 N3 113.13(19) . . ? N1 C2 S2 123.38(16) . . ? N3 C2 S2 123.50(16) . . ? C4 N3 C2 124.3(2) . . ? C4 N3 H3 117.5(19) . . ? C2 N3 H3 118.0(19) . . ? N3 C4 C5 121.0(2) . . ? N3 C4 H4 112.4(17) . . ? C5 C4 H4 126.6(17) . . ? C4 C5 C6 116.4(2) . . ? C4 C5 H5 121.8(19) . . ? C6 C5 H5 121.8(19) . . ? N1 C6 C5 120.6(2) . . ? N1 C6 H6 115.6(17) . . ? C5 C6 H6 123.8(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.87(3) 2.36(3) 3.1978(18) 162(3) . N3 H3 Br1 0.90(3) 2.38(3) 3.2282(18) 158(3) 3_556 C5 H5 Br1 0.97(3) 2.89(3) 3.700(3) 142(3) 2_564 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.531 _refine_diff_density_min -0.669 _refine_diff_density_rms 0.058 data_5 _database_code_depnum_ccdc_archive 'CCDC 919703' #TrackingRef '5.cif' _database_code_CSD 919699 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N2 S, I' _chemical_formula_sum 'C4 H5 I N2 S' _chemical_formula_weight 240.06 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.812(5) _cell_length_b 9.152(5) _cell_length_c 13.478(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1457.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1647 _cell_measurement_theta_min 2.8097 _cell_measurement_theta_max 28.1895 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 4.585 _exptl_absorpt_correction_T_min 0.91682 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '\w scans' _diffrn_reflns_number 6674 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 28.21 _reflns_number_total 1599 _reflns_number_gt 1107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_cell_refinement 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_data_reduction 'CrysAlis Pro (Oxford Diffraction (2009))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0289P)^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 1599 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 N1 N 0.4222(4) 0.3229(6) 0.4870(4) 0.0178(13) Uani 1 1 d . . . H1 H 0.4006 0.3845 0.5334 0.021 Uiso 1 1 calc R . . C2 C 0.5127(6) 0.2321(7) 0.5074(5) 0.0180(15) Uani 1 1 d . . . S2 S 0.57996(16) 0.2320(2) 0.61488(12) 0.0239(4) Uani 1 1 d . . . N3 N 0.5393(4) 0.1432(5) 0.4295(4) 0.0173(13) Uani 1 1 d . . . H3 H 0.5978 0.0846 0.4365 0.021 Uiso 1 1 calc R . . C4 C 0.4836(6) 0.1384(6) 0.3437(4) 0.0171(16) Uani 1 1 d . . . H4 H 0.5066 0.0714 0.2937 0.021 Uiso 1 1 calc R . . C5 C 0.3932(6) 0.2294(7) 0.3267(5) 0.0223(17) Uani 1 1 d . . . H5 H 0.3520 0.2270 0.2662 0.027 Uiso 1 1 calc R . . C6 C 0.3655(6) 0.3235(7) 0.4018(5) 0.0215(16) Uani 1 1 d . . . H6 H 0.3048 0.3904 0.3928 0.026 Uiso 1 1 calc R . . I1 I 0.27426(4) 0.55982(4) 0.63363(3) 0.01884(15) 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 N1 0.017(3) 0.020(3) 0.016(3) -0.003(2) -0.001(3) 0.002(3) C2 0.014(4) 0.027(4) 0.014(3) 0.001(3) 0.005(3) -0.003(3) S2 0.0197(11) 0.0367(11) 0.0154(9) -0.0026(8) -0.0024(8) 0.0012(8) N3 0.014(3) 0.020(3) 0.018(3) 0.000(2) 0.001(3) 0.004(2) C4 0.027(4) 0.016(3) 0.009(4) -0.001(3) -0.001(3) 0.003(3) C5 0.030(5) 0.025(4) 0.012(3) 0.006(3) -0.003(3) -0.010(3) C6 0.022(4) 0.018(4) 0.025(4) 0.007(3) 0.004(3) 0.003(3) I1 0.0172(3) 0.0162(2) 0.0231(2) -0.0038(2) 0.0033(2) -0.0015(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.329(8) . ? N1 C2 1.383(8) . ? C2 N3 1.365(7) . ? C2 S2 1.652(7) . ? N3 C4 1.332(8) . ? C4 C5 1.373(9) . ? C5 C6 1.368(9) . ? 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 C6 N1 C2 124.4(6) . . ? N3 C2 N1 112.5(6) . . ? N3 C2 S2 124.3(5) . . ? N1 C2 S2 123.2(5) . . ? C4 N3 C2 125.0(6) . . ? N3 C4 C5 120.6(6) . . ? C6 C5 C4 116.4(6) . . ? N1 C6 C5 121.1(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 I1 0.88 2.57 3.415(5) 160.1 . N3 H3 I1 0.88 2.64 3.447(5) 152.3 3_556 C5 H5 I1 0.95 3.04 3.796(7) 137.9 2_564 _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.576 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.203