#------------------------------------------------------------------------------ #$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201974 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/81/2218184.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_2218184 loop_ _publ_author_name 'Rizal, Mohd. Razali' 'Ali, Hapipah Mohd.' 'Ng, Seik Weng' _publ_section_title ; 5-Bromo-1H-indole-3-carbaldehyde thiosemicarbazone ; _journal_coeditor_code LH2609 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o918 _journal_paper_doi 10.1107/S160053680801101X _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C10 H9 Br N4 S' _chemical_formula_moiety 'C10 H9 Br N4 S' _chemical_formula_sum 'C10 H9 Br N4 S' _chemical_formula_weight 297.18 _chemical_name_systematic ; 5-Bromo-1H-indole-3-carboxaldehyde thiosemicarbazone ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 69.2800(10) _cell_angle_beta 79.9690(10) _cell_angle_gamma 72.8860(10) _cell_formula_units_Z 2 _cell_length_a 6.7731(2) _cell_length_b 8.7551(2) _cell_length_c 10.6539(2) _cell_measurement_reflns_used 6604 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.3 _cell_measurement_theta_min 4.0 _cell_volume 563.00(2) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'publCIF (Westrip, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker SMART APEX' _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 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6176 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.05 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.812 _exptl_absorpt_correction_T_max 0.516 _exptl_absorpt_correction_T_min 0.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 296 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.356 _refine_diff_density_min -0.396 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 161 _refine_ls_number_reflns 2563 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0242 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.1P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.0656 _reflns_number_gt 2281 _reflns_number_total 2563 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh2609.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2218184 _cod_database_fobs_code 2218184 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Br Br1 0.51693(4) 0.13022(2) 0.31237(2) 0.02102(9) Uani d . 1 S S1 0.01187(9) 0.22591(6) 1.06142(5) 0.01534(12) Uani d . 1 N N1 0.2717(3) 0.8577(2) 0.27383(17) 0.0153(4) Uani d D 1 N N2 0.1383(3) 0.4698(2) 0.68281(16) 0.0116(3) Uani d . 1 N N3 0.0718(3) 0.4342(2) 0.81750(16) 0.0118(3) Uani d D 1 N N4 0.1492(3) 0.1567(2) 0.83268(18) 0.0169(4) Uani d D 1 C C1 0.1846(3) 0.8475(3) 0.4006(2) 0.0151(4) Uani d . 1 H H1 0.1266 0.9415 0.4320 0.018 Uiso calc R 1 C C2 0.3383(3) 0.6981(2) 0.2626(2) 0.0122(4) Uani d . 1 C C3 0.4355(3) 0.6471(3) 0.1529(2) 0.0142(4) Uani d . 1 H H3 0.4641 0.7265 0.0687 0.017 Uiso calc R 1 C C4 0.4889(3) 0.4765(3) 0.1711(2) 0.0131(4) Uani d . 1 H H4 0.5573 0.4359 0.0990 0.016 Uiso calc R 1 C C5 0.4422(3) 0.3633(2) 0.2960(2) 0.0127(4) Uani d . 1 C C6 0.3464(3) 0.4108(2) 0.40581(19) 0.0118(4) Uani d . 1 H H6 0.3184 0.3300 0.4893 0.014 Uiso calc R 1 C C7 0.2917(3) 0.5832(2) 0.38933(19) 0.0109(4) Uani d . 1 C C8 0.1921(3) 0.6825(2) 0.4770(2) 0.0120(4) Uani d . 1 C C9 0.1249(3) 0.6266(2) 0.6176(2) 0.0127(4) Uani d . 1 H H9 0.0693 0.7074 0.6633 0.015 Uiso calc R 1 C C10 0.0822(3) 0.2737(2) 0.8937(2) 0.0123(4) Uani d . 1 H H1N 0.254(5) 0.953(2) 0.207(2) 0.028(7) Uiso d D 1 H H3N 0.037(4) 0.510(2) 0.858(2) 0.013(6) Uiso d D 1 H H4N1 0.137(4) 0.0533(17) 0.876(2) 0.023(7) Uiso d D 1 H H4N2 0.173(5) 0.190(4) 0.7452(11) 0.035(8) Uiso d D 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 Br1 0.02971(15) 0.01243(12) 0.02039(12) -0.00512(9) 0.00410(9) -0.00765(8) S1 0.0217(3) 0.0111(2) 0.0101(2) -0.0029(2) 0.00152(19) -0.00200(18) N1 0.0190(10) 0.0104(8) 0.0119(8) -0.0022(7) 0.0015(7) -0.0005(6) N2 0.0105(8) 0.0144(8) 0.0100(8) -0.0056(6) 0.0021(6) -0.0034(6) N3 0.0154(9) 0.0112(8) 0.0091(7) -0.0032(7) 0.0020(6) -0.0051(6) N4 0.0239(10) 0.0117(8) 0.0144(8) -0.0050(7) 0.0044(7) -0.0056(7) C1 0.0176(11) 0.0133(9) 0.0127(9) -0.0021(8) 0.0005(8) -0.0045(8) C2 0.0120(10) 0.0108(9) 0.0134(9) -0.0032(7) -0.0023(8) -0.0025(7) C3 0.0121(10) 0.0167(10) 0.0119(9) -0.0036(8) -0.0015(8) -0.0022(7) C4 0.0109(10) 0.0174(10) 0.0111(9) -0.0028(8) -0.0020(7) -0.0049(7) C5 0.0113(10) 0.0106(9) 0.0165(9) -0.0031(7) -0.0014(8) -0.0042(7) C6 0.0102(10) 0.0124(9) 0.0117(9) -0.0030(7) -0.0017(7) -0.0021(7) C7 0.0090(10) 0.0132(9) 0.0103(9) -0.0028(7) -0.0012(7) -0.0032(7) C8 0.0114(10) 0.0116(9) 0.0131(9) -0.0035(8) -0.0011(7) -0.0037(7) C9 0.0107(10) 0.0137(9) 0.0133(9) -0.0024(8) -0.0003(8) -0.0049(7) C10 0.0103(10) 0.0129(9) 0.0130(9) -0.0029(7) 0.0001(7) -0.0038(7) 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C2 109.25(17) C1 N1 H1N 122.5(19) C2 N1 H1N 126.2(18) C9 N2 N3 115.12(17) C10 N3 N2 119.25(16) C10 N3 H3N 117.5(16) N2 N3 H3N 122.8(16) C10 N4 H4N1 119.9(17) C10 N4 H4N2 118.1(19) H4N1 N4 H4N2 120(3) N1 C1 C8 110.69(18) N1 C1 H1 124.7 C8 C1 H1 124.7 N1 C2 C3 129.70(18) N1 C2 C7 107.45(17) C3 C2 C7 122.85(18) C4 C3 C2 117.27(18) C4 C3 H3 121.4 C2 C3 H3 121.4 C3 C4 C5 119.81(18) C3 C4 H4 120.1 C5 C4 H4 120.1 C6 C5 C4 123.94(18) C6 C5 Br1 118.76(15) C4 C5 Br1 117.30(15) C5 C6 C7 117.04(18) C5 C6 H6 121.5 C7 C6 H6 121.5 C6 C7 C2 119.09(17) C6 C7 C8 134.17(18) C2 C7 C8 106.75(17) C1 C8 C9 124.92(18) C1 C8 C7 105.86(17) C9 C8 C7 129.10(18) N2 C9 C8 121.41(18) N2 C9 H9 119.3 C8 C9 H9 119.3 N4 C10 N3 117.36(18) N4 C10 S1 122.58(16) N3 C10 S1 120.06(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C5 1.9032(19) S1 C10 1.699(2) N1 C1 1.359(3) N1 C2 1.378(3) N1 H1N 0.878(10) N2 C9 1.284(3) N2 N3 1.378(2) N3 C10 1.339(3) N3 H3N 0.876(10) N4 C10 1.331(3) N4 H4N1 0.880(10) N4 H4N2 0.873(10) C1 C8 1.376(3) C1 H1 0.9500 C2 C3 1.388(3) C2 C7 1.418(3) C3 C4 1.379(3) C3 H3 0.9500 C4 C5 1.399(3) C4 H4 0.9500 C5 C6 1.372(3) C6 C7 1.398(3) C6 H6 0.9500 C7 C8 1.447(3) C8 C9 1.437(3) C9 H9 0.9500 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 N1 H1n S1 1_564 0.880(10) 2.60(2) 3.390(2) 150(3) yes N3 H3n S1 2_567 0.880(10) 2.650(10) 3.508(2) 167(2) yes N4 H4n1 S1 2_557 0.880(10) 2.740(10) 3.569(2) 158(2) yes 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 C9 N2 N3 C10 -179.30(19) C2 N1 C1 C8 0.5(3) C1 N1 C2 C3 180.0(2) C1 N1 C2 C7 -0.6(2) N1 C2 C3 C4 178.9(2) C7 C2 C3 C4 -0.6(3) C2 C3 C4 C5 0.8(3) C3 C4 C5 C6 -0.8(3) C3 C4 C5 Br1 179.01(16) C4 C5 C6 C7 0.6(3) Br1 C5 C6 C7 -179.25(15) C5 C6 C7 C2 -0.3(3) C5 C6 C7 C8 -179.8(2) N1 C2 C7 C6 -179.18(18) C3 C2 C7 C6 0.3(3) N1 C2 C7 C8 0.4(2) C3 C2 C7 C8 179.9(2) N1 C1 C8 C9 176.0(2) N1 C1 C8 C7 -0.2(3) C6 C7 C8 C1 179.4(2) C2 C7 C8 C1 -0.2(2) C6 C7 C8 C9 3.4(4) C2 C7 C8 C9 -176.2(2) N3 N2 C9 C8 178.80(19) C1 C8 C9 N2 -179.4(2) C7 C8 C9 N2 -4.0(4) N2 N3 C10 N4 -2.8(3) N2 N3 C10 S1 177.10(15) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655478