#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/24/2212434.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_2212434 loop_ _publ_author_name 'Jian-Gang Wang' 'Fang-Fang Jian' 'Xiao-Yan Ren' 'Shi-Hong Kan' _publ_section_title ; 1-[1-(2-Chlorophenyl)ethylidene]thiosemicarbazide ; _journal_coeditor_code AT2214 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1160 _journal_page_last o1161 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C9 H10 Cl N3 S' _chemical_formula_moiety 'C9 H10 Cl N3 S' _chemical_formula_sum 'C9 H10 Cl N3 S' _chemical_formula_weight 227.71 _chemical_name_systematic ; 1-[1-(2-Chlorophenyl)ethylidene]thiosemicarbazide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 120.52(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.482(2) _cell_length_b 8.1751(16) _cell_length_c 13.232(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14 _cell_measurement_theta_min 4 _cell_volume 1070.0(6) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'NRCVAX (Gabe et al., 1989)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \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 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4746 _diffrn_reflns_theta_full 27.04 _diffrn_reflns_theta_max 27.04 _diffrn_reflns_theta_min 2.06 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.515 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.339 _refine_diff_density_min -0.326 _refine_ls_extinction_coef 0.022(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.300 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 2235 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.300 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0585 _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^)+(0.042P)^2^+0.9107P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1393 _refine_ls_wR_factor_ref 0.1403 _reflns_number_gt 2183 _reflns_number_total 2235 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file at2214.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2212434 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' 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' 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 Cl Cl1 -0.04181(9) -0.00032(12) 0.24067(8) 0.0588(3) Uani d . 1 S S1 0.56965(9) 0.33901(10) 0.28227(10) 0.0591(3) Uani d . 1 N N1 0.3106(2) 0.2367(3) 0.3811(2) 0.0389(5) Uani d . 1 N N2 0.4067(2) 0.2137(3) 0.3491(2) 0.0422(6) Uani d . 1 H H2A 0.4334 0.1177 0.3433 0.051 Uiso calc R 1 N N3 0.4148(3) 0.4916(3) 0.3450(3) 0.0570(8) Uani d . 1 H H3A 0.3583 0.4935 0.3694 0.068 Uiso calc R 1 H H3B 0.4439 0.5817 0.3322 0.068 Uiso calc R 1 C C1 0.4568(3) 0.3507(4) 0.3271(3) 0.0405(6) Uani d . 1 C C2 0.2835(4) -0.0621(4) 0.3890(4) 0.0569(9) Uani d . 1 H H2B 0.3499 -0.0700 0.3656 0.085 Uiso calc R 1 H H2C 0.2021 -0.1163 0.3323 0.085 Uiso calc R 1 H H2D 0.3176 -0.1130 0.4643 0.085 Uiso calc R 1 C C3 0.2540(3) 0.1133(4) 0.3968(2) 0.0376(6) Uani d . 1 C C4 0.1538(3) 0.1595(3) 0.4318(2) 0.0362(6) Uani d . 1 C C5 0.0187(3) 0.1137(3) 0.3688(2) 0.0373(6) Uani d . 1 C C6 -0.0730(3) 0.1637(4) 0.4006(3) 0.0458(7) Uani d . 1 H H6A -0.1629 0.1313 0.3568 0.055 Uiso calc R 1 C C7 -0.0308(3) 0.2613(4) 0.4971(3) 0.0520(8) Uani d . 1 H H7A -0.0919 0.2950 0.5193 0.062 Uiso calc R 1 C C8 0.1027(4) 0.3098(4) 0.5614(3) 0.0548(8) Uani d . 1 H H8A 0.1313 0.3765 0.6268 0.066 Uiso calc R 1 C C9 0.1937(3) 0.2597(4) 0.5290(3) 0.0464(7) Uani d . 1 H H9A 0.2833 0.2933 0.5729 0.056 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 Cl1 0.0548(5) 0.0687(6) 0.0574(5) -0.0207(4) 0.0319(4) -0.0221(4) S1 0.0597(5) 0.0437(5) 0.1054(7) -0.0053(4) 0.0650(5) -0.0040(4) N1 0.0355(11) 0.0428(13) 0.0454(13) 0.0006(10) 0.0255(10) 0.0048(10) N2 0.0396(12) 0.0396(13) 0.0594(15) 0.0040(10) 0.0339(12) 0.0046(11) N3 0.0680(18) 0.0400(14) 0.093(2) -0.0024(13) 0.0630(18) -0.0006(14) C1 0.0365(14) 0.0405(15) 0.0504(16) -0.0025(12) 0.0263(13) 0.0000(13) C2 0.061(2) 0.0429(18) 0.089(3) 0.0024(15) 0.054(2) 0.0098(17) C3 0.0369(14) 0.0427(15) 0.0390(14) 0.0018(12) 0.0235(12) 0.0047(12) C4 0.0381(14) 0.0368(14) 0.0401(14) 0.0019(11) 0.0245(12) 0.0050(12) C5 0.0421(14) 0.0354(14) 0.0407(14) -0.0048(11) 0.0256(12) 0.0006(11) C6 0.0393(15) 0.0492(18) 0.0566(18) -0.0013(13) 0.0299(14) 0.0057(14) C7 0.059(2) 0.056(2) 0.0619(19) 0.0085(16) 0.0455(17) 0.0052(16) C8 0.066(2) 0.059(2) 0.0499(18) -0.0011(17) 0.0370(16) -0.0092(16) C9 0.0420(15) 0.0573(19) 0.0402(15) -0.0031(14) 0.0211(13) -0.0027(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C5 1.741(3) S1 C1 1.679(3) N1 C3 1.273(4) N1 N2 1.381(3) N2 C1 1.356(4) N2 H2A 0.8600 N3 C1 1.316(4) N3 H3A 0.8600 N3 H3B 0.8600 C2 C3 1.489(4) C2 H2B 0.9600 C2 H2C 0.9600 C2 H2D 0.9600 C3 C4 1.491(4) C4 C5 1.388(4) C4 C9 1.392(4) C5 C6 1.379(4) C6 C7 1.368(5) C6 H6A 0.9300 C7 C8 1.380(5) C7 H7A 0.9300 C8 C9 1.377(4) C8 H8A 0.9300 C9 H9A 0.9300 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C3 N1 N2 119.8(2) C1 N2 N1 116.5(2) C1 N2 H2A 121.8 N1 N2 H2A 121.8 C1 N3 H3A 120.0 C1 N3 H3B 120.0 H3A N3 H3B 120.0 N3 C1 N2 116.7(2) N3 C1 S1 122.2(2) N2 C1 S1 121.1(2) C3 C2 H2B 109.5 C3 C2 H2C 109.5 H2B C2 H2C 109.5 C3 C2 H2D 109.5 H2B C2 H2D 109.5 H2C C2 H2D 109.5 N1 C3 C2 126.8(3) N1 C3 C4 112.9(2) C2 C3 C4 120.3(2) C5 C4 C9 117.2(3) C5 C4 C3 123.3(3) C9 C4 C3 119.5(3) C6 C5 C4 122.0(3) C6 C5 Cl1 117.8(2) C4 C5 Cl1 120.0(2) C7 C6 C5 119.6(3) C7 C6 H6A 120.2 C5 C6 H6A 120.2 C6 C7 C8 119.9(3) C6 C7 H7A 120.0 C8 C7 H7A 120.0 C9 C8 C7 120.2(3) C9 C8 H8A 119.9 C7 C8 H8A 119.9 C8 C9 C4 121.1(3) C8 C9 H9A 119.4 C4 C9 H9A 119.4 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 C3 N1 N2 C1 176.2(3) N1 N2 C1 N3 3.8(4) N1 N2 C1 S1 -177.6(2) N2 N1 C3 C2 2.6(5) N2 N1 C3 C4 179.6(2) N1 C3 C4 C5 122.1(3) C2 C3 C4 C5 -60.7(4) N1 C3 C4 C9 -54.8(4) C2 C3 C4 C9 122.4(3) C9 C4 C5 C6 -0.4(4) C3 C4 C5 C6 -177.3(3) C9 C4 C5 Cl1 175.8(2) C3 C4 C5 Cl1 -1.1(4) C4 C5 C6 C7 -0.1(4) Cl1 C5 C6 C7 -176.3(2) C5 C6 C7 C8 0.4(5) C6 C7 C8 C9 -0.3(5) C7 C8 C9 C4 -0.2(5) C5 C4 C9 C8 0.5(5) C3 C4 C9 C8 177.6(3) 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 _geom_hbond_publ_flag N2 H2A S1 2_645 0.8600 2.8100 3.600(3) 153.00 yes N3 H3A N1 . 0.8600 2.1900 2.566(4) 106.00 yes N3 H3B S1 2_655 0.8600 2.5500 3.353(3) 156.00 yes C2 H2B N2 . 0.9600 2.4500 2.850(5) 105.00 yes C2 H2B S1 2_645 0.9600 2.6600 3.538(5) 152.00 yes C2 H2C Cl1 . 0.9600 2.6000 3.258(5) 126.00 yes _cod_database_fobs_code 2212434 _journal_paper_doi 10.1107/S1600536807004473