#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 11 _journal_issue 2 _journal_year 2020 _journal_page_first 156 _journal_page_last 159 #============================================================================== data_bmy276_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N3 O2 S' _chemical_formula_sum 'C13 H15 N3 O2 S' _chemical_formula_weight 277.34 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 'Triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3016(9) _cell_length_b 7.7380(9) _cell_length_c 12.9815(16) _cell_angle_alpha 103.581(4) _cell_angle_beta 102.153(4) _cell_angle_gamma 102.409(4) _cell_volume 669.46(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 31185 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 26.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9026 _exptl_absorpt_correction_T_max 0.9575 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _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 ; Bruker SMART APEX CCD area-detector diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 83.66 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31184 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 26.73 _reflns_number_total 2822 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL- (Sheldrick, 2008)' _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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^)+(0.0643P)^2^+0.4797P] 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 2822 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.078 _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 0.34362(10) 0.00177(10) 0.10961(6) 0.0521(2) Uani 1 1 d . . . O1 O 0.1329(3) 0.0972(2) 0.38526(15) 0.0562(5) Uani 1 1 d . . . O2 O -0.6135(3) -0.4995(3) 0.15067(18) 0.0630(6) Uani 1 1 d . . . N1 N 0.0041(3) -0.1024(3) 0.15373(17) 0.0417(5) Uani 1 1 d . . . N2 N 0.1875(3) 0.2031(3) 0.24225(17) 0.0401(5) Uani 1 1 d D . . N3 N -0.2914(3) -0.3914(3) 0.16648(18) 0.0473(5) Uani 1 1 d . . . C1 C 0.2355(3) 0.4237(3) 0.42243(19) 0.0383(5) Uani 1 1 d . . . C2 C 0.2770(4) 0.5764(4) 0.3848(2) 0.0495(6) Uani 1 1 d . . . H2 H 0.2777 0.5608 0.3117 0.059 Uiso 1 1 calc R . . C3 C 0.3175(5) 0.7525(4) 0.4557(3) 0.0647(8) Uani 1 1 d . . . H3 H 0.3435 0.8550 0.4298 0.078 Uiso 1 1 calc R . . C4 C 0.3194(5) 0.7762(4) 0.5642(3) 0.0670(9) Uani 1 1 d . . . H4 H 0.3472 0.8948 0.6117 0.080 Uiso 1 1 calc R . . C5 C 0.2806(5) 0.6262(5) 0.6023(2) 0.0635(8) Uani 1 1 d . . . H5 H 0.2838 0.6428 0.6761 0.076 Uiso 1 1 calc R . . C6 C 0.2367(4) 0.4504(4) 0.5321(2) 0.0509(6) Uani 1 1 d . . . H6 H 0.2076 0.3487 0.5582 0.061 Uiso 1 1 calc R . . C7 C 0.1826(3) 0.2283(3) 0.3516(2) 0.0396(5) Uani 1 1 d . . . C8 C 0.1672(3) 0.0287(3) 0.17034(19) 0.0386(5) Uani 1 1 d . . . C9 C -0.1768(3) -0.0687(3) 0.1752(2) 0.0404(5) Uani 1 1 d . . . H9A H -0.2694 -0.0827 0.1061 0.048 Uiso 1 1 calc R . . H9B H -0.1490 0.0573 0.2215 0.048 Uiso 1 1 calc R . . C10 C -0.2655(4) -0.2017(3) 0.2315(2) 0.0463(6) Uani 1 1 d . . . H10A H -0.1808 -0.1774 0.3047 0.056 Uiso 1 1 calc R . . H10B H -0.3906 -0.1850 0.2386 0.056 Uiso 1 1 calc R . . C11 C -0.1147(4) -0.4279(4) 0.1436(3) 0.0581(8) Uani 1 1 d . . . H11A H -0.1454 -0.5532 0.0959 0.070 Uiso 1 1 calc R . . H11B H -0.0222 -0.4175 0.2120 0.070 Uiso 1 1 calc R . . C12 C -0.0231(4) -0.2928(3) 0.0887(2) 0.0518(7) Uani 1 1 d . . . H12A H 0.1019 -0.3103 0.0819 0.062 Uiso 1 1 calc R . . H12B H -0.1066 -0.3161 0.0152 0.062 Uiso 1 1 calc R . . C13 C -0.4612(4) -0.5204(4) 0.1318(2) 0.0519(7) Uani 1 1 d . . . H13 H -0.4649 -0.6368 0.0895 0.062 Uiso 1 1 calc R . . H2A H 0.255(4) 0.297(3) 0.228(2) 0.060(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0433(4) 0.0475(4) 0.0681(5) 0.0121(3) 0.0300(3) 0.0088(3) O1 0.0753(13) 0.0379(10) 0.0517(11) 0.0173(9) 0.0146(10) 0.0068(9) O2 0.0498(11) 0.0609(13) 0.0722(14) 0.0182(11) 0.0260(10) -0.0047(9) N1 0.0338(10) 0.0346(11) 0.0500(12) 0.0018(9) 0.0165(9) 0.0026(8) N2 0.0400(11) 0.0304(10) 0.0453(11) 0.0071(9) 0.0158(9) 0.0011(8) N3 0.0467(12) 0.0352(11) 0.0551(13) 0.0060(9) 0.0215(10) 0.0019(9) C1 0.0295(11) 0.0376(12) 0.0423(13) 0.0072(10) 0.0057(9) 0.0077(9) C2 0.0550(15) 0.0395(14) 0.0498(15) 0.0098(12) 0.0132(12) 0.0096(12) C3 0.075(2) 0.0366(15) 0.077(2) 0.0112(14) 0.0202(17) 0.0115(14) C4 0.0666(19) 0.0503(18) 0.066(2) -0.0113(15) 0.0136(16) 0.0153(15) C5 0.0665(19) 0.070(2) 0.0450(16) 0.0013(15) 0.0123(14) 0.0213(16) C6 0.0541(16) 0.0533(16) 0.0434(14) 0.0131(12) 0.0114(12) 0.0143(13) C7 0.0362(12) 0.0361(13) 0.0419(13) 0.0104(10) 0.0079(10) 0.0050(10) C8 0.0358(12) 0.0364(12) 0.0412(13) 0.0095(10) 0.0118(10) 0.0062(10) C9 0.0328(11) 0.0359(13) 0.0488(14) 0.0066(11) 0.0139(10) 0.0058(9) C10 0.0445(13) 0.0397(13) 0.0490(14) 0.0032(11) 0.0204(11) 0.0034(11) C11 0.0546(16) 0.0359(14) 0.078(2) 0.0037(14) 0.0235(15) 0.0091(12) C12 0.0438(14) 0.0376(14) 0.0618(17) -0.0066(12) 0.0238(12) 0.0008(11) C13 0.0594(17) 0.0378(14) 0.0502(15) 0.0095(12) 0.0211(13) -0.0055(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 C8 1.670(2) . ? O1 C7 1.212(3) . ? O2 C13 1.223(3) . ? N1 C8 1.328(3) . ? N1 C12 1.464(3) . ? N1 C9 1.470(3) . ? N2 C7 1.395(3) . ? N2 C8 1.407(3) . ? N2 H2A 0.866(10) . ? N3 C13 1.326(3) . ? N3 C11 1.453(3) . ? N3 C10 1.461(3) . ? C1 C2 1.380(4) . ? C1 C6 1.387(4) . ? C1 C7 1.493(3) . ? C2 C3 1.384(4) . ? C2 H2 0.9300 . ? C3 C4 1.374(5) . ? C3 H3 0.9300 . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 C6 1.375(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C9 C10 1.509(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.516(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C12 120.9(2) . . ? C8 N1 C9 124.9(2) . . ? C12 N1 C9 112.95(18) . . ? C7 N2 C8 122.6(2) . . ? C7 N2 H2A 116(2) . . ? C8 N2 H2A 116(2) . . ? C13 N3 C11 122.6(2) . . ? C13 N3 C10 123.0(2) . . ? C11 N3 C10 114.4(2) . . ? C2 C1 C6 118.9(2) . . ? C2 C1 C7 124.2(2) . . ? C6 C1 C7 116.9(2) . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 120.5(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O1 C7 N2 121.1(2) . . ? O1 C7 C1 122.5(2) . . ? N2 C7 C1 116.4(2) . . ? N1 C8 N2 116.6(2) . . ? N1 C8 S1 124.69(18) . . ? N2 C8 S1 118.66(17) . . ? N1 C9 C10 111.1(2) . . ? N1 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N1 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N3 C10 C9 109.4(2) . . ? N3 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N3 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? N3 C11 C12 111.0(2) . . ? N3 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N3 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N1 C12 C11 110.2(2) . . ? N1 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N1 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O2 C13 N3 125.6(3) . . ? O2 C13 H13 117.2 . . ? N3 C13 H13 117.2 . . ? 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 C6 C1 C2 C3 -0.5(4) . . . . ? C7 C1 C2 C3 177.6(3) . . . . ? C1 C2 C3 C4 1.0(5) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C3 C4 C5 C6 -0.9(5) . . . . ? C4 C5 C6 C1 1.4(5) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? C7 C1 C6 C5 -178.9(2) . . . . ? C8 N2 C7 O1 -10.7(4) . . . . ? C8 N2 C7 C1 171.2(2) . . . . ? C2 C1 C7 O1 -174.4(2) . . . . ? C6 C1 C7 O1 3.7(4) . . . . ? C2 C1 C7 N2 3.7(3) . . . . ? C6 C1 C7 N2 -178.2(2) . . . . ? C12 N1 C8 N2 -174.2(2) . . . . ? C9 N1 C8 N2 19.7(4) . . . . ? C12 N1 C8 S1 7.5(4) . . . . ? C9 N1 C8 S1 -158.54(19) . . . . ? C7 N2 C8 N1 58.5(3) . . . . ? C7 N2 C8 S1 -123.2(2) . . . . ? C8 N1 C9 C10 -136.7(2) . . . . ? C12 N1 C9 C10 56.3(3) . . . . ? C13 N3 C10 C9 -125.5(3) . . . . ? C11 N3 C10 C9 55.1(3) . . . . ? N1 C9 C10 N3 -54.1(3) . . . . ? C13 N3 C11 C12 125.6(3) . . . . ? C10 N3 C11 C12 -54.9(3) . . . . ? C8 N1 C12 C11 137.6(3) . . . . ? C9 N1 C12 C11 -54.7(3) . . . . ? N3 C11 C12 N1 52.8(3) . . . . ? C11 N3 C13 O2 178.1(3) . . . . ? C10 N3 C13 O2 -1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.357 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.063