#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2216045.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2216045 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Guodong Yao' 'Shizhu Sun' 'Dacheng Li' 'Daqi Wang' 'Jianmin Dou' _publ_section_title ; N'-[1-(2-Thienyl)ethylidene]pyridine-2-carbohydrazide ; _journal_coeditor_code LH2521 _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o4324 _journal_page_last o4324 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C12 H11 N3 O S' _chemical_formula_moiety 'C12 H11 N3 O S' _chemical_formula_sum 'C12 H11 N3 O S' _chemical_formula_weight 245.30 _chemical_name_systematic ; N'-[1-(2-Thienyl)ethylidene]pyridine-2-carbohydrazide ; _symmetry_cell_setting Monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 104.857(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.162(2) _cell_length_b 9.8259(16) _cell_length_c 10.2461(17) _cell_measurement_reflns_used 2156 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.208 _cell_measurement_theta_min 2.702 _cell_volume 1183.5(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'SHELXTL (Sheldrick, 1997b)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5755 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 1.73 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_T_max 0.9451 _exptl_absorpt_correction_T_min 0.8682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour light-yellow _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.316 _refine_diff_density_min -0.264 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2088 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 2.083 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0464 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0845P)^2^+0.601P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1327 _refine_ls_wR_factor_ref 0.1541 _reflns_number_gt 1531 _reflns_number_total 2088 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh2521.cif 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' 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy N N1 0.1445(4) 0.8579(5) 0.0924(5) 0.0484(12) Uani d . 1 H H1 0.1133 0.8729 0.0084 0.058 Uiso calc RD 1 N N2 0.2426(4) 0.9265(4) 0.1575(4) 0.0447(11) Uani d . 1 N N3 -0.0534(4) 0.7579(5) -0.0438(4) 0.0482(12) Uani d . 1 O O1 0.1393(3) 0.7400(4) 0.2790(4) 0.0579(12) Uani d . 1 S S1 0.43434(14) 1.0654(2) 0.33637(15) 0.0677(7) Uani d . 1 C C1 0.0987(4) 0.7684(6) 0.1611(5) 0.0431(13) Uani d . 1 C C2 -0.0087(4) 0.7049(5) 0.0788(5) 0.0416(12) Uani d . 1 C C3 -0.0575(5) 0.5980(6) 0.1313(6) 0.0512(15) Uani d . 1 H H3 -0.0241 0.5642 0.2171 0.061 Uiso calc R 1 C C4 -0.1572(5) 0.5424(7) 0.0530(6) 0.0585(16) Uani d . 1 H H4 -0.1922 0.4701 0.0850 0.070 Uiso calc R 1 C C5 -0.2034(5) 0.5957(7) -0.0723(6) 0.0595(17) Uani d . 1 H H5 -0.2705 0.5604 -0.1269 0.071 Uiso calc R 1 C C6 -0.1494(5) 0.7020(7) -0.1162(6) 0.0568(16) Uani d . 1 H H6 -0.1817 0.7372 -0.2017 0.068 Uiso calc R 1 C C7 0.2513(5) 1.0330(7) -0.0622(6) 0.0583(16) Uani d . 1 H H7A 0.1828 0.9830 -0.1004 0.087 Uiso calc RD 1 H H7B 0.3093 1.0058 -0.1051 0.087 Uiso calc R 1 H H7C 0.2368 1.1286 -0.0761 0.087 Uiso calc R 1 C C8 0.2906(4) 1.0040(5) 0.0875(5) 0.0414(12) Uani d . 1 C C9 0.3943(4) 1.0717(5) 0.1632(5) 0.0426(13) Uani d . 1 C C10 0.4717(5) 1.1431(7) 0.1159(6) 0.0607(17) Uani d . 1 H H10 0.4650 1.1585 0.0247 0.073 Uiso calc R 1 C C11 0.5637(5) 1.1916(7) 0.2204(7) 0.0663(18) Uani d . 1 H H11 0.6242 1.2413 0.2049 0.080 Uiso calc R 1 C C12 0.5543(5) 1.1585(7) 0.3430(7) 0.0596(17) Uani d . 1 H H12 0.6068 1.1831 0.4227 0.071 Uiso calc R 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.040(2) 0.055(3) 0.044(2) -0.009(2) -0.0010(19) 0.006(2) N2 0.035(2) 0.048(3) 0.046(3) -0.004(2) 0.0006(19) 0.003(2) N3 0.041(3) 0.054(3) 0.047(3) -0.004(2) 0.007(2) 0.000(2) O1 0.052(2) 0.070(3) 0.046(2) -0.008(2) 0.0029(18) 0.010(2) S1 0.0572(11) 0.0936(14) 0.0457(10) -0.0204(9) 0.0013(7) -0.0024(8) C1 0.037(3) 0.045(3) 0.046(3) 0.003(2) 0.008(2) 0.001(2) C2 0.039(3) 0.042(3) 0.045(3) 0.002(2) 0.012(2) -0.002(2) C3 0.048(3) 0.057(4) 0.049(3) -0.003(3) 0.013(3) 0.003(3) C4 0.054(4) 0.062(4) 0.062(4) -0.016(3) 0.021(3) -0.002(3) C5 0.048(3) 0.073(4) 0.056(4) -0.018(3) 0.011(3) -0.013(3) C6 0.050(3) 0.068(4) 0.048(3) -0.004(3) 0.004(3) -0.002(3) C7 0.061(4) 0.064(4) 0.044(3) -0.010(3) 0.003(3) -0.001(3) C8 0.040(3) 0.040(3) 0.041(3) 0.002(2) 0.005(2) 0.001(2) C9 0.041(3) 0.038(3) 0.046(3) 0.001(2) 0.006(2) 0.001(2) C10 0.060(4) 0.063(4) 0.057(4) -0.018(3) 0.012(3) 0.002(3) C11 0.054(4) 0.062(4) 0.081(5) -0.019(3) 0.014(3) -0.010(4) C12 0.043(3) 0.066(4) 0.062(4) -0.007(3) -0.001(3) -0.015(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1.335(7) n N1 N2 1.384(6) n N1 H1 0.8600 ? N2 C8 1.285(7) n N3 C6 1.331(7) ? N3 C2 1.339(7) ? O1 C1 1.215(6) n S1 C12 1.709(6) n S1 C9 1.716(6) n C1 C2 1.497(7) ? C2 C3 1.382(8) ? C3 C4 1.384(8) ? C3 H3 0.9300 ? C4 C5 1.367(9) ? C4 H4 0.9300 ? C5 C6 1.370(9) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 C8 1.512(7) ? C7 H7A 0.9600 ? C7 H7B 0.9600 ? C7 H7C 0.9600 ? C8 C9 1.460(7) ? C9 C10 1.359(8) ? C10 C11 1.419(9) ? C10 H10 0.9300 ? C11 C12 1.330(9) ? C11 H11 0.9300 ? C12 H12 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_publ_flag C1 N1 N2 119.5(4) n C1 N1 H1 120.2 ? N2 N1 H1 120.2 ? C8 N2 N1 118.6(4) n C6 N3 C2 116.7(5) ? C12 S1 C9 92.0(3) ? O1 C1 N1 123.9(5) n O1 C1 C2 122.6(5) n N1 C1 C2 113.6(5) n N3 C2 C3 123.3(5) ? N3 C2 C1 116.9(5) ? C3 C2 C1 119.8(5) ? C2 C3 C4 118.3(6) ? C2 C3 H3 120.8 ? C4 C3 H3 120.8 ? C5 C4 C3 118.8(6) ? C5 C4 H4 120.6 ? C3 C4 H4 120.6 ? C4 C5 C6 119.0(6) ? C4 C5 H5 120.5 ? C6 C5 H5 120.5 ? N3 C6 C5 123.9(6) ? N3 C6 H6 118.1 ? C5 C6 H6 118.1 ? C8 C7 H7A 109.5 ? C8 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? C8 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? N2 C8 C9 115.3(5) n N2 C8 C7 127.4(5) ? C9 C8 C7 117.4(5) ? C10 C9 C8 128.9(5) ? C10 C9 S1 110.4(4) ? C8 C9 S1 120.7(4) ? C9 C10 C11 112.9(6) ? C9 C10 H10 123.5 ? C11 C10 H10 123.5 ? C12 C11 C10 112.8(6) ? C12 C11 H11 123.6 ? C10 C11 H11 123.6 ? C11 C12 S1 111.9(5) ? C11 C12 H12 124.1 ? S1 C12 H12 124.1 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C7 H7A O1 4_575 0.96 2.50 3.250(7) 134.5 N1 H1 O1 4_575 0.86 2.69 3.337(6) 133.1 C11 H11 N2 2_655 0.93 2.60 3.306(8) 133.2 _cod_database_code 2216045