# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/468 data_MM9550 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H7 N3 O S' _chemical_formula_weight 205.24 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0492 0.0322 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6773(14) _cell_length_b 8.191(2) _cell_length_c 9.319(2) _cell_angle_alpha 71.480(15) _cell_angle_beta 79.503(15) _cell_angle_gamma 73.308(15) _cell_volume 460.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Dichroic _exptl_crystal_colour Yellow/red _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method ? _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 2.869 _exptl_absorpt_correction_type 'Face-indexed numerical' _exptl_absorpt_correction_T_min 0.6464 _exptl_absorpt_correction_T_max 0.7909 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1493 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.03 _diffrn_reflns_theta_max 62.92 _reflns_number_total 1493 _reflns_number_observed 1406 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.1672P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0102(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1487 _refine_ls_number_parameters 136 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_obs 0.0350 _refine_ls_wR_factor_all 0.1056 _refine_ls_wR_factor_obs 0.0942 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.038 _refine_ls_restrained_S_all 1.128 _refine_ls_restrained_S_obs 1.037 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.02491(7) 0.79976(6) 0.67190(5) 0.0395(2) Uani 1 d . . C2 C 0.0038(3) 0.8904(2) 0.8243(2) 0.0367(4) Uani 1 d . . N2 N -0.1768(3) 0.9242(2) 0.9052(2) 0.0463(4) Uani 1 d D . H2A H -0.2915(23) 0.9151(34) 0.8734(27) 0.069(7) Uiso 1 d D . H2B H -0.1868(36) 0.9742(26) 0.9802(16) 0.055(6) Uiso 1 d D . N3 N 0.1772(2) 0.9177(2) 0.8534(2) 0.0398(4) Uani 1 d . . C4 C 0.3436(3) 0.8687(2) 0.7550(2) 0.0383(4) Uani 1 d . . O4 O 0.5234(2) 0.8726(2) 0.7613(2) 0.0538(4) Uani 1 d . . C5 C 0.2874(3) 0.8080(2) 0.6356(2) 0.0354(4) Uani 1 d . . C6 C 0.4246(3) 0.7711(3) 0.5193(2) 0.0415(5) Uani 1 d . . H6A H 0.5591(3) 0.7857(3) 0.5138(2) 0.050 Uiso 1 calc R . C7 C 0.3797(3) 0.7096(3) 0.4007(2) 0.0417(5) Uani 1 d . . N8 N 0.1959(3) 0.6656(2) 0.4220(2) 0.0499(4) Uani 1 d . . C9 C 0.1528(4) 0.6065(3) 0.3159(3) 0.0591(6) Uani 1 d . . H9A H 0.0259(4) 0.5752(3) 0.3299(3) 0.071 Uiso 1 calc R . C10 C 0.2842(5) 0.5895(3) 0.1879(3) 0.0645(7) Uani 1 d . . H10A H 0.2473(5) 0.5477(3) 0.1171(3) 0.077 Uiso 1 calc R . C11 C 0.4718(4) 0.6354(3) 0.1661(3) 0.0639(7) Uani 1 d . . H11A H 0.5637(4) 0.6262(3) 0.0795(3) 0.077 Uiso 1 calc R . C12 C 0.5227(4) 0.6952(3) 0.2741(2) 0.0527(5) Uani 1 d . . H12A H 0.6500(4) 0.7252(3) 0.2625(2) 0.063 Uiso 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 0.0353(3) 0.0558(3) 0.0407(3) -0.0255(2) -0.0057(2) -0.0171(2) C2 0.0362(10) 0.0450(10) 0.0367(10) -0.0168(8) -0.0076(8) -0.0135(8) N2 0.0352(9) 0.0720(11) 0.0471(10) -0.0342(8) -0.0044(7) -0.0170(8) N3 0.0359(8) 0.0551(9) 0.0398(9) -0.0229(7) -0.0091(7) -0.0145(7) C4 0.0366(10) 0.0474(10) 0.0387(10) -0.0161(8) -0.0087(8) -0.0149(8) O4 0.0366(8) 0.0840(11) 0.0593(9) -0.0368(8) -0.0072(6) -0.0232(7) C5 0.0338(9) 0.0438(9) 0.0354(9) -0.0149(7) -0.0077(7) -0.0128(7) C6 0.0363(10) 0.0503(11) 0.0432(11) -0.0177(9) -0.0060(8) -0.0124(8) C7 0.0427(11) 0.0451(10) 0.0398(10) -0.0172(8) -0.0057(8) -0.0076(8) N8 0.0493(10) 0.0627(11) 0.0494(10) -0.0289(8) -0.0070(8) -0.0155(8) C9 0.0643(14) 0.0685(14) 0.0599(14) -0.0323(11) -0.0164(11) -0.0174(11) C10 0.091(2) 0.0621(14) 0.0511(13) -0.0300(11) -0.0205(13) -0.0111(13) C11 0.086(2) 0.0618(14) 0.0420(12) -0.0261(11) 0.0013(12) -0.0077(13) C12 0.0545(13) 0.0555(12) 0.0472(12) -0.0206(10) -0.0007(10) -0.0078(10) _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 C5 1.741(2) . ? S1 C2 1.768(2) . ? C2 N2 1.307(2) . ? C2 N3 1.329(2) . ? N3 C4 1.357(2) . ? C4 O4 1.223(2) . ? C4 C5 1.495(2) . ? C5 C6 1.338(3) . ? C6 C7 1.459(3) . ? C7 N8 1.340(3) . ? C7 C12 1.389(3) . ? N8 C9 1.335(3) . ? C9 C10 1.366(4) . ? C10 C11 1.371(4) . ? C11 C12 1.379(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 C5 S1 C2 88.02(8) . . ? N2 C2 N3 122.7(2) . . ? N2 C2 S1 119.81(13) . . ? N3 C2 S1 117.45(14) . . ? C2 N3 C4 111.06(15) . . ? O4 C4 N3 124.2(2) . . ? O4 C4 C5 122.2(2) . . ? N3 C4 C5 113.57(15) . . ? C6 C5 C4 122.7(2) . . ? C6 C5 S1 127.67(14) . . ? C4 C5 S1 109.63(13) . . ? C5 C6 C7 125.2(2) . . ? N8 C7 C12 122.3(2) . . ? N8 C7 C6 116.4(2) . . ? C12 C7 C6 121.3(2) . . ? C9 N8 C7 117.4(2) . . ? N8 C9 C10 123.8(2) . . ? C9 C10 C11 118.6(2) . . ? C10 C11 C12 119.2(2) . . ? C11 C12 C7 118.6(2) . . ? _refine_diff_density_max 0.178 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.044 data_MM957 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H7 N3 O S' _chemical_formula_weight 205.24 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0492 0.0322 '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 P2(1)/n 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 4.709(3) _cell_length_b 10.278(4) _cell_length_c 18.676(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.11(5) _cell_angle_gamma 90.00 _cell_volume 903.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method ? _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 2.926 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1599 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.74 _diffrn_reflns_theta_max 61.92 _reflns_number_total 1417 _reflns_number_observed 1380 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.5554P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0198(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1416 _refine_ls_number_parameters 134 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_obs 0.0355 _refine_ls_wR_factor_all 0.1020 _refine_ls_wR_factor_obs 0.0968 _refine_ls_goodness_of_fit_all 1.048 _refine_ls_goodness_of_fit_obs 1.054 _refine_ls_restrained_S_all 1.095 _refine_ls_restrained_S_obs 1.054 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.0188(3) 0.2856(2) 1.04341(8) 0.0325(4) Uani 1 d D . H1A H -0.1302(38) 0.3555(13) 1.0499(12) 0.039 Uiso 1 d D . C2 C 0.1804(4) 0.2795(2) 0.99267(10) 0.0321(5) Uani 1 d . . S2 S 0.26787(13) 0.39074(5) 0.93503(3) 0.0465(3) Uani 1 d . . N3 N 0.3065(3) 0.1589(2) 0.99983(9) 0.0333(4) Uani 1 d D . H3A H 0.4415(32) 0.1321(21) 0.9703(9) 0.040 Uiso 1 d D . C4 C 0.1992(4) 0.0888(2) 1.05481(10) 0.0318(5) Uani 1 d . . O4 O 0.2665(3) -0.02075(14) 1.07344(8) 0.0426(4) Uani 1 d . . C5 C -0.0146(4) 0.1756(2) 1.08613(10) 0.0306(4) Uani 1 d . . C6 C -0.1495(4) 0.1481(2) 1.14620(10) 0.0329(5) Uani 1 d . . H6A H -0.1116(4) 0.0672(2) 1.16672(10) 0.039 Uiso 1 calc R . C7 C -0.3482(4) 0.2304(2) 1.18283(10) 0.0298(4) Uani 1 d . . N8 N -0.4457(3) 0.3369(2) 1.14773(9) 0.0360(4) Uani 1 d . . C9 C -0.6322(4) 0.4104(2) 1.18130(12) 0.0405(5) Uani 1 d . . H9A H -0.7043(4) 0.4835(2) 1.15761(12) 0.049 Uiso 1 calc R . C10 C -0.7246(5) 0.3846(2) 1.24899(12) 0.0441(5) Uani 1 d . . H10A H -0.8562(5) 0.4389(2) 1.26982(12) 0.053 Uiso 1 calc R . C11 C -0.6199(5) 0.2778(2) 1.28530(11) 0.0452(6) Uani 1 d . . H11A H -0.6762(5) 0.2589(2) 1.33137(11) 0.054 Uiso 1 calc R . C12 C -0.4289(4) 0.1993(2) 1.25152(11) 0.0378(5) Uani 1 d . . H12A H -0.3545(4) 0.1260(2) 1.27458(11) 0.045 Uiso 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 0.0347(8) 0.0311(9) 0.0322(9) 0.0018(7) 0.0068(7) 0.0073(7) C2 0.0352(10) 0.0330(10) 0.0281(10) -0.0016(8) 0.0004(8) 0.0024(8) S2 0.0610(4) 0.0400(4) 0.0395(4) 0.0085(2) 0.0147(3) 0.0046(2) N3 0.0357(9) 0.0319(9) 0.0330(9) -0.0011(7) 0.0101(7) 0.0037(7) C4 0.0309(10) 0.0326(11) 0.0321(10) -0.0025(8) 0.0047(8) 0.0005(8) O4 0.0489(9) 0.0309(8) 0.0492(9) 0.0062(6) 0.0182(7) 0.0104(6) C5 0.0295(9) 0.0313(10) 0.0310(10) -0.0001(8) 0.0019(7) 0.0023(8) C6 0.0334(10) 0.0307(10) 0.0347(10) 0.0027(8) 0.0043(8) 0.0032(8) C7 0.0281(9) 0.0310(10) 0.0306(10) -0.0017(8) 0.0038(7) -0.0018(7) N8 0.0361(9) 0.0335(9) 0.0386(9) 0.0025(7) 0.0056(7) 0.0045(7) C9 0.0400(11) 0.0333(11) 0.0485(12) -0.0009(9) 0.0047(9) 0.0061(9) C10 0.0429(12) 0.0420(12) 0.0481(13) -0.0112(10) 0.0120(9) 0.0034(9) C11 0.0542(13) 0.0481(13) 0.0343(11) -0.0034(10) 0.0142(10) -0.0001(10) C12 0.0415(11) 0.0378(11) 0.0342(11) 0.0033(8) 0.0058(8) 0.0026(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 N1 C2 1.359(3) . ? N1 C5 1.384(3) . ? C2 N3 1.379(3) . ? C2 S2 1.633(2) . ? N3 C4 1.366(3) . ? C4 O4 1.217(2) . ? C4 C5 1.481(3) . ? C5 C6 1.340(3) . ? C6 C7 1.452(3) . ? C7 N8 1.348(3) . ? C7 C12 1.389(3) . ? N8 C9 1.332(3) . ? C9 C10 1.378(3) . ? C10 C11 1.373(3) . ? C11 C12 1.378(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 C2 N1 C5 111.6(2) . . ? N1 C2 N3 106.2(2) . . ? N1 C2 S2 128.6(2) . . ? N3 C2 S2 125.11(15) . . ? C4 N3 C2 112.2(2) . . ? O4 C4 N3 127.1(2) . . ? O4 C4 C5 128.1(2) . . ? N3 C4 C5 104.8(2) . . ? C6 C5 N1 131.1(2) . . ? C6 C5 C4 123.6(2) . . ? N1 C5 C4 105.1(2) . . ? C5 C6 C7 127.3(2) . . ? N8 C7 C12 122.4(2) . . ? N8 C7 C6 117.3(2) . . ? C12 C7 C6 120.3(2) . . ? C9 N8 C7 116.8(2) . . ? N8 C9 C10 124.0(2) . . ? C11 C10 C9 119.2(2) . . ? C10 C11 C12 118.1(2) . . ? C11 C12 C7 119.6(2) . . ? _refine_diff_density_max 0.234 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.045 data_mm9601 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H6 N2 O2 S' _chemical_formula_weight 206.22 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9555(8) _cell_length_b 8.9958(15) _cell_length_c 10.773(2) _cell_angle_alpha 108.603(9) _cell_angle_beta 95.338(12) _cell_angle_gamma 95.933(12) _cell_volume 448.66(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method ? _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2844 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2571 _reflns_number_observed 2200 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0720P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2570 _refine_ls_number_parameters 131 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_obs 0.0375 _refine_ls_wR_factor_all 0.1119 _refine_ls_wR_factor_obs 0.1055 _refine_ls_goodness_of_fit_all 1.128 _refine_ls_goodness_of_fit_obs 1.156 _refine_ls_restrained_S_all 1.130 _refine_ls_restrained_S_obs 1.156 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.45645(7) 0.24391(4) 0.44033(3) 0.03381(12) Uani 1 d . . C2 C 0.7096(3) 0.1348(2) 0.47913(14) 0.0322(3) Uani 1 d . . O2 O 0.8149(2) 0.15652(14) 0.59110(11) 0.0413(3) Uani 1 d . . N3 N 0.7667(3) 0.02366(15) 0.36790(12) 0.0341(3) Uani 1 d D . H3A H 0.8944(32) -0.0376(21) 0.3762(21) 0.059(6) Uiso 1 d D . C4 C 0.6194(3) 0.0122(2) 0.24970(15) 0.0362(3) Uani 1 d . . O4 O 0.6437(3) -0.0834(2) 0.14454(12) 0.0538(3) Uani 1 d . . C5 C 0.4318(3) 0.1345(2) 0.27202(14) 0.0326(3) Uani 1 d . . C6 C 0.2787(3) 0.1546(2) 0.17116(15) 0.0365(3) Uani 1 d . . H6A H 0.2904(3) 0.0870(2) 0.08673(15) 0.044 Uiso 1 calc R . C7 C 0.0953(3) 0.2735(2) 0.18219(15) 0.0350(3) Uani 1 d . . N8 N 0.0697(3) 0.3654(2) 0.30528(14) 0.0385(3) Uani 1 d . . C9 C -0.0922(4) 0.4768(2) 0.3177(2) 0.0450(4) Uani 1 d . . H9A H -0.1088(4) 0.5421(2) 0.4023(2) 0.054 Uiso 1 calc R . C10 C -0.2373(4) 0.5007(2) 0.2110(2) 0.0523(4) Uani 1 d . . H10A H -0.3492(4) 0.5797(2) 0.2239(2) 0.063 Uiso 1 calc R . C11 C -0.2122(4) 0.4046(3) 0.0854(2) 0.0556(5) Uani 1 d . . H11A H -0.3085(4) 0.4174(3) 0.0120(2) 0.067 Uiso 1 calc R . C12 C -0.0425(4) 0.2892(2) 0.0696(2) 0.0455(4) Uani 1 d . . H12A H -0.0209(4) 0.2236(2) -0.0142(2) 0.055 Uiso 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 0.0363(2) 0.0349(2) 0.0311(2) 0.00854(13) 0.00667(13) 0.01460(13) C2 0.0310(6) 0.0328(7) 0.0342(7) 0.0117(5) 0.0056(5) 0.0080(5) O2 0.0455(6) 0.0444(6) 0.0333(5) 0.0102(5) 0.0006(4) 0.0161(5) N3 0.0327(6) 0.0364(6) 0.0339(6) 0.0096(5) 0.0049(5) 0.0149(5) C4 0.0367(7) 0.0392(7) 0.0339(7) 0.0100(6) 0.0076(6) 0.0149(6) O4 0.0646(8) 0.0595(8) 0.0346(6) 0.0039(5) 0.0057(5) 0.0355(6) C5 0.0333(6) 0.0340(7) 0.0312(6) 0.0088(5) 0.0073(5) 0.0119(5) C6 0.0379(7) 0.0393(7) 0.0330(7) 0.0099(6) 0.0061(6) 0.0139(6) C7 0.0325(7) 0.0377(7) 0.0371(7) 0.0143(6) 0.0042(6) 0.0097(6) N8 0.0395(6) 0.0389(7) 0.0385(7) 0.0121(5) 0.0058(5) 0.0133(5) C9 0.0477(9) 0.0372(8) 0.0510(9) 0.0120(7) 0.0103(7) 0.0157(7) C10 0.0506(10) 0.0455(9) 0.0656(12) 0.0209(9) 0.0060(9) 0.0222(8) C11 0.0561(11) 0.0628(12) 0.0571(11) 0.0298(9) -0.0010(9) 0.0255(9) C12 0.0468(9) 0.0547(10) 0.0384(8) 0.0173(7) 0.0031(7) 0.0182(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 C5 1.7513(15) . ? S1 C2 1.7694(15) . ? C2 O2 1.215(2) . ? C2 N3 1.369(2) . ? N3 C4 1.376(2) . ? C4 O4 1.209(2) . ? C4 C5 1.489(2) . ? C5 C6 1.338(2) . ? C6 C7 1.457(2) . ? C7 N8 1.346(2) . ? C7 C12 1.390(2) . ? N8 C9 1.329(2) . ? C9 C10 1.386(3) . ? C10 C11 1.379(3) . ? C11 C12 1.382(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 C5 S1 C2 90.93(7) . . ? O2 C2 N3 125.22(13) . . ? O2 C2 S1 123.45(11) . . ? N3 C2 S1 111.33(11) . . ? C2 N3 C4 117.06(12) . . ? O4 C4 N3 123.99(14) . . ? O4 C4 C5 126.22(14) . . ? N3 C4 C5 109.78(12) . . ? C6 C5 C4 121.39(13) . . ? C6 C5 S1 127.71(12) . . ? C4 C5 S1 110.85(10) . . ? C5 C6 C7 125.62(14) . . ? N8 C7 C12 122.86(14) . . ? N8 C7 C6 116.60(13) . . ? C12 C7 C6 120.54(14) . . ? C9 N8 C7 117.67(14) . . ? N8 C9 C10 123.3(2) . . ? C11 C10 C9 118.5(2) . . ? C10 C11 C12 119.3(2) . . ? C11 C12 C7 118.3(2) . . ? _refine_diff_density_max 0.327 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.054 data_mm9620 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H6 N2 O S2' _chemical_formula_weight 222.28 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0492 0.0322 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8818(7) _cell_length_b 11.0381(13) _cell_length_c 11.4248(14) _cell_angle_alpha 76.449(8) _cell_angle_beta 87.344(13) _cell_angle_gamma 82.699(14) _cell_volume 471.97(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 3.98 _cell_measurement_theta_max 27.73 _exptl_crystal_description Needle_plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.83 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method ? _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 4.832 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.58 _diffrn_reflns_number 1625 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 60.00 _reflns_number_total 1391 _reflns_number_observed 1320 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+0.1625P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1389 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_obs 0.0420 _refine_ls_wR_factor_all 0.1208 _refine_ls_wR_factor_obs 0.1165 _refine_ls_goodness_of_fit_all 1.053 _refine_ls_goodness_of_fit_obs 1.061 _refine_ls_restrained_S_all 1.070 _refine_ls_restrained_S_obs 1.061 _refine_ls_shift/esd_max 0.034 _refine_ls_shift/esd_mean 0.005 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.21221(15) 0.80634(6) 0.74686(5) 0.0343(3) Uani 1 d . . C2 C 0.1663(6) 0.6619(2) 0.8460(2) 0.0345(6) Uani 1 d . . S2 S 0.3272(2) 0.52668(7) 0.81816(7) 0.0483(3) Uani 1 d . . N3 N -0.0224(5) 0.6798(2) 0.9455(2) 0.0367(5) Uani 1 d . . H3A H -0.0623(5) 0.6174(2) 1.0033(2) 0.044 Uiso 1 calc R . C4 C -0.1472(6) 0.8012(2) 0.9504(2) 0.0337(6) Uani 1 d . . O4 O -0.3321(5) 0.8267(2) 1.0320(2) 0.0498(5) Uani 1 d . . C5 C -0.0273(6) 0.8900(2) 0.8424(2) 0.0311(6) Uani 1 d . . C6 C -0.1068(6) 1.0139(2) 0.8262(2) 0.0347(6) Uani 1 d . . H6A H -0.2336(6) 1.0431(2) 0.8872(2) 0.042 Uiso 1 calc R . C7 C -0.0117(6) 1.1073(2) 0.7210(2) 0.0355(6) Uani 1 d . . N8 N 0.1657(6) 1.0625(2) 0.6332(2) 0.0412(6) Uani 1 d . . C9 C 0.2469(8) 1.1462(3) 0.5343(2) 0.0486(7) Uani 1 d . . H9A H 0.3688(8) 1.1166(3) 0.4726(2) 0.058 Uiso 1 calc R . C10 C 0.1612(9) 1.2730(3) 0.5185(3) 0.0544(8) Uani 1 d . . H10A H 0.2225(9) 1.3276(3) 0.4476(3) 0.065 Uiso 1 calc R . C11 C -0.0173(9) 1.3183(3) 0.6092(3) 0.0560(8) Uani 1 d . . H11A H -0.0772(9) 1.4041(3) 0.6011(3) 0.067 Uiso 1 calc R . C12 C -0.1057(8) 1.2341(3) 0.7123(3) 0.0458(7) Uani 1 d . . H12A H -0.2266(8) 1.2621(3) 0.7750(3) 0.055 Uiso 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 0.0396(4) 0.0343(4) 0.0281(4) -0.0082(3) 0.0105(3) -0.0032(3) C2 0.0364(12) 0.0354(15) 0.0310(12) -0.0077(10) 0.0047(10) -0.0037(10) S2 0.0592(5) 0.0339(5) 0.0504(5) -0.0133(3) 0.0195(3) -0.0008(3) N3 0.0486(12) 0.0278(12) 0.0300(11) -0.0027(8) 0.0126(9) -0.0037(9) C4 0.0379(13) 0.0352(15) 0.0268(12) -0.0075(10) 0.0066(10) -0.0022(10) O4 0.0668(12) 0.0440(12) 0.0350(10) -0.0091(9) 0.0210(9) -0.0015(10) C5 0.0342(12) 0.0329(14) 0.0257(12) -0.0078(10) 0.0055(9) -0.0024(10) C6 0.0408(13) 0.0330(15) 0.0293(12) -0.0092(10) 0.0070(10) 0.0003(11) C7 0.0396(13) 0.0350(15) 0.0302(13) -0.0051(10) 0.0017(10) -0.0026(10) N8 0.0493(13) 0.0388(14) 0.0331(11) -0.0060(10) 0.0072(10) -0.0028(10) C9 0.059(2) 0.051(2) 0.0318(14) -0.0028(12) 0.0100(12) -0.0081(14) C10 0.068(2) 0.048(2) 0.040(2) 0.0075(13) 0.0039(14) -0.0134(14) C11 0.076(2) 0.032(2) 0.054(2) 0.0013(13) -0.001(2) -0.0042(14) C12 0.057(2) 0.037(2) 0.0397(15) -0.0072(12) 0.0039(12) 0.0016(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 C2 1.751(3) . ? S1 C5 1.752(2) . ? C2 N3 1.363(3) . ? C2 S2 1.639(3) . ? N3 C4 1.379(3) . ? C4 O4 1.214(3) . ? C4 C5 1.482(3) . ? C5 C6 1.334(4) . ? C6 C7 1.455(4) . ? C7 N8 1.344(4) . ? C7 C12 1.382(4) . ? N8 C9 1.335(3) . ? C9 C10 1.368(4) . ? C10 C11 1.376(5) . ? C11 C12 1.379(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 C2 S1 C5 92.31(12) . . ? N3 C2 S2 126.5(2) . . ? N3 C2 S1 110.3(2) . . ? S2 C2 S1 123.3(2) . . ? C2 N3 C4 117.9(2) . . ? O4 C4 N3 123.0(2) . . ? O4 C4 C5 127.2(2) . . ? N3 C4 C5 109.8(2) . . ? C6 C5 C4 121.9(2) . . ? C6 C5 S1 128.4(2) . . ? C4 C5 S1 109.7(2) . . ? C5 C6 C7 125.5(2) . . ? N8 C7 C12 122.7(2) . . ? N8 C7 C6 116.0(2) . . ? C12 C7 C6 121.3(2) . . ? C9 N8 C7 117.1(2) . . ? N8 C9 C10 123.8(3) . . ? C9 C10 C11 118.8(3) . . ? C12 C11 C10 118.8(3) . . ? C11 C12 C7 118.9(3) . . ? _refine_diff_density_max 0.383 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.069