#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205194.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_2205194
loop_
_publ_author_name
'Bian, He-Dong'
'Guo, Gui-Quan'
'Yu, Qing'
'Liang, Hong'
'Yang, Xiao-E'
'Zhu, Li-Gang'
_publ_section_title
;
N-Benzoylthiosemicarbazide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o639
_journal_page_last               o640
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H9 N3 O1 S1'
_chemical_formula_moiety         'C8 H9 N3 O1 S1'
_chemical_formula_sum            'C8 H9 N3 O S'
_chemical_formula_weight         195.24
_chemical_name_systematic
;
N-Benzoylthiosemicarbazide
;
_symmetry_cell_setting           triclinic
_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                83.554(7)
_cell_angle_beta                 75.631(7)
_cell_angle_gamma                84.998(7)
_cell_formula_units_Z            4
_cell_length_a                   8.237(3)
_cell_length_b                   8.438(3)
_cell_length_c                   14.590(6)
_cell_measurement_reflns_used    905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.62
_cell_volume                     974.3(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker 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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5064
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.45
_diffrn_standards_decay_%        <1%
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0422
_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^)+(0.066P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2413
_reflns_number_total             3408
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ac6151.cif
_[local]_cod_chemical_formula_sum_orig 'C8 H9 N3 O1 S1'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'multiscan' changed to 'multi-scan'
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 
;
_cod_database_code               2205194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
S1 0.20558(8) 0.44361(8) 0.96438(5) 0.0403(2) Uani d . 1 S
S2 1.32622(9) 0.95077(8) -0.07452(5) 0.0478(2) Uani d . 1 S
O1 0.5848(3) 0.7382(4) 0.70866(17) 0.0863(9) Uani d . 1 O
O2 1.1635(3) 0.7167(3) 0.24999(15) 0.0663(6) Uani d . 1 O
N1 0.6476(3) 0.6042(3) 0.83852(17) 0.0404(6) Uani d D 1 N
H1 0.707(3) 0.599(3) 0.8799(14) 0.037(8) Uiso d D 1 H
N2 0.4791(3) 0.5889(3) 0.88217(17) 0.0431(6) Uani d D 1 N
H2 0.422(3) 0.675(2) 0.899(2) 0.069(11) Uiso d D 1 H
N3 0.5057(3) 0.3180(3) 0.87782(19) 0.0465(6) Uani d D 1 N
H3A 0.6077(17) 0.323(3) 0.8447(18) 0.051(9) Uiso d D 1 H
H3B 0.463(3) 0.228(2) 0.899(2) 0.057(9) Uiso d D 1 H
N4 0.9933(3) 0.7925(3) 0.15231(17) 0.0477(6) Uani d D 1 N
H4 0.897(2) 0.801(4) 0.140(3) 0.083(12) Uiso d D 1 H
N5 1.1247(3) 0.8012(3) 0.07203(17) 0.0447(6) Uani d D 1 N
H5 1.150(3) 0.720(2) 0.0404(16) 0.039(8) Uiso d D 1 H
N6 1.1315(4) 1.0684(3) 0.0787(2) 0.0564(7) Uani d D 1 N
H6A 1.050(3) 1.055(4) 0.1284(15) 0.074(12) Uiso d D 1 H
H6B 1.165(4) 1.158(2) 0.047(2) 0.073(11) Uiso d D 1 H
C1 0.9941(3) 0.6650(3) 0.7617(2) 0.0450(7) Uani d . 1 C
H1A 0.9693 0.5860 0.8121 0.054 Uiso calc R 1 H
C2 1.1558(3) 0.7113(4) 0.7282(2) 0.0583(8) Uani d . 1 C
H2A 1.2403 0.6620 0.7555 0.070 Uiso calc R 1 H
C3 1.1938(4) 0.8289(4) 0.6553(3) 0.0682(10) Uani d . 1 C
H3 1.3034 0.8599 0.6333 0.082 Uiso calc R 1 H
C4 1.0709(5) 0.9005(5) 0.6151(3) 0.0855(13) Uani d . 1 C
H4A 1.0969 0.9810 0.5657 0.103 Uiso calc R 1 H
C5 0.9074(4) 0.8550(5) 0.6467(3) 0.0723(10) Uani d . 1 C
H5A 0.8243 0.9045 0.6185 0.087 Uiso calc R 1 H
C6 0.8679(3) 0.7357(3) 0.72037(19) 0.0423(7) Uani d . 1 C
C7 0.6889(3) 0.6944(4) 0.7533(2) 0.0454(7) Uani d . 1 C
C8 0.4128(3) 0.4473(3) 0.90322(18) 0.0332(6) Uani d . 1 C
C9 0.8911(5) 0.6543(5) 0.4042(3) 0.0815(11) Uani d . 1 C
H9 0.9985 0.6221 0.4114 0.098 Uiso calc R 1 H
C10 0.7542(7) 0.6333(6) 0.4809(3) 0.1065(16) Uani d . 1 C
H10 0.7701 0.5862 0.5390 0.128 Uiso calc R 1 H
C11 0.5989(7) 0.6804(6) 0.4717(4) 0.1105(17) Uani d . 1 C
H11 0.5075 0.6670 0.5236 0.133 Uiso calc R 1 H
C12 0.5750(5) 0.7477(7) 0.3869(4) 0.1216(19) Uani d . 1 C
H12 0.4671 0.7795 0.3806 0.146 Uiso calc R 1 H
C13 0.7110(4) 0.7692(5) 0.3093(3) 0.0863(13) Uani d . 1 C
H13 0.6938 0.8158 0.2514 0.104 Uiso calc R 1 H
C14 0.8695(4) 0.7223(3) 0.3178(2) 0.0511(8) Uani d . 1 C
C15 1.0215(4) 0.7418(3) 0.2391(2) 0.0439(7) Uani d . 1 C
C16 1.1862(3) 0.9415(3) 0.03145(19) 0.0384(6) Uani d . 1 C
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
S1 0.0275(3) 0.0386(4) 0.0503(5) -0.0041(3) -0.0012(3) -0.0019(3)
S2 0.0476(4) 0.0360(4) 0.0510(5) -0.0051(3) 0.0040(3) -0.0014(3)
O1 0.0432(13) 0.154(3) 0.0584(16) -0.0189(14) -0.0172(11) 0.0246(16)
O2 0.0440(12) 0.0970(18) 0.0524(14) 0.0131(11) -0.0074(10) -0.0069(12)
N1 0.0287(12) 0.0451(13) 0.0445(15) -0.0096(10) -0.0033(11) 0.0022(11)
N2 0.0287(11) 0.0376(14) 0.0552(16) -0.0056(10) 0.0052(10) -0.0035(11)
N3 0.0312(13) 0.0359(14) 0.0663(18) -0.0037(11) 0.0002(12) -0.0049(12)
N4 0.0391(14) 0.0592(16) 0.0414(15) -0.0061(12) -0.0041(12) -0.0008(12)
N5 0.0481(14) 0.0385(14) 0.0418(14) -0.0067(11) 0.0019(11) -0.0058(11)
N6 0.0650(18) 0.0398(16) 0.0557(18) -0.0048(14) 0.0034(15) -0.0073(14)
C1 0.0376(15) 0.0468(17) 0.0461(17) -0.0058(12) -0.0008(13) -0.0040(13)
C2 0.0366(16) 0.068(2) 0.069(2) -0.0091(15) -0.0091(15) -0.0061(18)
C3 0.0442(18) 0.079(2) 0.076(3) -0.0215(17) 0.0023(17) -0.008(2)
C4 0.068(2) 0.093(3) 0.083(3) -0.031(2) -0.004(2) 0.035(2)
C5 0.0515(19) 0.096(3) 0.062(2) -0.0153(18) -0.0112(17) 0.027(2)
C6 0.0363(15) 0.0519(17) 0.0369(16) -0.0095(13) -0.0038(12) -0.0029(13)
C7 0.0356(15) 0.0607(18) 0.0384(17) -0.0063(13) -0.0055(13) -0.0032(14)
C8 0.0282(13) 0.0381(15) 0.0334(14) -0.0037(11) -0.0070(11) -0.0030(11)
C9 0.081(3) 0.103(3) 0.050(2) 0.006(2) -0.0025(19) 0.000(2)
C10 0.125(4) 0.124(4) 0.050(3) -0.004(3) 0.012(3) 0.002(2)
C11 0.105(4) 0.118(4) 0.077(3) -0.014(3) 0.040(3) -0.007(3)
C12 0.057(3) 0.172(5) 0.112(4) -0.007(3) 0.016(3) 0.009(4)
C13 0.049(2) 0.127(4) 0.067(3) 0.001(2) 0.0050(18) 0.010(2)
C14 0.0511(18) 0.0513(18) 0.0453(18) -0.0045(14) 0.0000(14) -0.0059(14)
C15 0.0474(17) 0.0383(16) 0.0436(18) -0.0016(13) -0.0047(13) -0.0087(13)
C16 0.0371(14) 0.0343(15) 0.0438(16) -0.0021(11) -0.0105(12) -0.0022(12)
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 N2 118.5(2)
C7 N1 H1 122.3(17)
N2 N1 H1 111.1(17)
C8 N2 N1 122.0(2)
C8 N2 H2 122(2)
N1 N2 H2 116(2)
C8 N3 H3A 121.1(19)
C8 N3 H3B 117(2)
H3A N3 H3B 122(3)
C15 N4 N5 120.8(2)
C15 N4 H4 124(2)
N5 N4 H4 114(2)
C16 N5 N4 121.7(2)
C16 N5 H5 118.5(18)
N4 N5 H5 118.1(17)
C16 N6 H6A 116(2)
C16 N6 H6B 114(2)
H6A N6 H6B 128(3)
C2 C1 C6 120.1(3)
C2 C1 H1A 120.0
C6 C1 H1A 120.0
C3 C2 C1 120.7(3)
C3 C2 H2A 119.6
C1 C2 H2A 119.6
C4 C3 C2 119.7(3)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.8(3)
C3 C4 H4A 119.6
C5 C4 H4A 119.6
C6 C5 C4 119.9(3)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 C1 118.8(3)
C5 C6 C7 117.7(3)
C1 C6 C7 123.5(3)
O1 C7 N1 121.2(3)
O1 C7 C6 123.0(3)
N1 C7 C6 115.8(2)
N3 C8 N2 119.8(2)
N3 C8 S1 122.9(2)
N2 C8 S1 117.36(19)
C14 C9 C10 120.6(4)
C14 C9 H9 119.7
C10 C9 H9 119.7
C11 C10 C9 120.3(5)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 120.0(4)
C10 C11 H11 120.0
C12 C11 H11 120.0
C11 C12 C13 120.3(4)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 120.3(4)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C9 118.6(3)
C13 C14 C15 123.8(3)
C9 C14 C15 117.6(3)
O2 C15 N4 121.2(3)
O2 C15 C14 123.2(3)
N4 C15 C14 115.7(3)
N6 C16 N5 116.9(3)
N6 C16 S2 122.8(2)
N5 C16 S2 120.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.720(2)
S2 C16 1.682(3)
O1 C7 1.210(3)
O2 C15 1.216(3)
N1 C7 1.365(4)
N1 N2 1.387(3)
N1 H1 0.860(10)
N2 C8 1.329(3)
N2 H2 0.858(10)
N3 C8 1.311(3)
N3 H3A 0.861(10)
N3 H3B 0.855(10)
N4 C15 1.359(4)
N4 N5 1.384(3)
N4 H4 0.854(10)
N5 C16 1.344(3)
N5 H5 0.851(10)
N6 C16 1.324(4)
N6 H6A 0.861(10)
N6 H6B 0.866(10)
C1 C2 1.376(4)
C1 C6 1.386(4)
C1 H1A 0.9300
C2 C3 1.366(4)
C2 H2A 0.9300
C3 C4 1.357(5)
C3 H3 0.9300
C4 C5 1.384(4)
C4 H4A 0.9300
C5 C6 1.384(4)
C5 H5A 0.9300
C6 C7 1.493(4)
C9 C14 1.371(5)
C9 C10 1.385(5)
C9 H9 0.9300
C10 C11 1.341(7)
C10 H10 0.9300
C11 C12 1.355(7)
C11 H11 0.9300
C12 C13 1.389(5)
C12 H12 0.9300
C13 C14 1.363(4)
C13 H13 0.9300
C14 C15 1.481(4)
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
N6 H6B S1 1_664 0.870(10) 2.584(12) 3.439(3) 169(3)
N5 H5 S1 1_654 0.850(10) 2.650(11) 3.495(3) 172(2)
N4 H4 S1 2_666 0.850(10) 2.99(3) 3.503(3) 120(3)
N4 H4 S2 2_775 0.850(10) 2.90(2) 3.584(3) 138(3)
N3 H3B S2 1_446 0.850(10) 2.635(12) 3.475(3) 167(3)
N3 H3A O2 2_766 0.860(10) 2.069(13) 2.907(3) 164(3)
N2 H2 S2 1_456 0.860(10) 2.431(13) 3.268(3) 165(3)
N1 H1 S1 2_667 0.860(10) 2.530(13) 3.358(3) 162(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
C7 N1 N2 C8 121.3(3)
C15 N4 N5 C16 -103.9(3)
C6 C1 C2 C3 1.1(5)
C1 C2 C3 C4 -0.3(5)
C2 C3 C4 C5 -0.4(6)
C3 C4 C5 C6 0.2(6)
C4 C5 C6 C1 0.5(5)
C4 C5 C6 C7 178.4(3)
C2 C1 C6 C5 -1.2(4)
C2 C1 C6 C7 -179.0(3)
N2 N1 C7 O1 -12.3(4)
N2 N1 C7 C6 167.2(2)
C5 C6 C7 O1 13.7(5)
C1 C6 C7 O1 -168.5(3)
C5 C6 C7 N1 -165.7(3)
C1 C6 C7 N1 12.1(4)
N1 N2 C8 N3 -3.8(4)
N1 N2 C8 S1 175.8(2)
C14 C9 C10 C11 -0.6(7)
C9 C10 C11 C12 0.6(8)
C10 C11 C12 C13 -0.5(9)
C11 C12 C13 C14 0.3(8)
C12 C13 C14 C9 -0.2(6)
C12 C13 C14 C15 -179.5(4)
C10 C9 C14 C13 0.4(6)
C10 C9 C14 C15 179.7(4)
N5 N4 C15 O2 6.8(4)
N5 N4 C15 C14 -174.1(2)
C13 C14 C15 O2 171.2(3)
C9 C14 C15 O2 -8.1(5)
C13 C14 C15 N4 -7.8(5)
C9 C14 C15 N4 172.8(3)
N4 N5 C16 N6 9.0(4)
N4 N5 C16 S2 -171.1(2)