#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/19/2201947.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_2201947
loop_
_publ_author_name
'M. Sukeri M. Yusof'
'Bohari M. Yamin'
'Mustaffa Shamsudin'
_publ_section_title
;
 N-(N-Benzoylhydrazinocarbothioyl)benzamide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o810
_journal_page_last               o811
_journal_paper_doi               10.1107/S1600536803010110
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C15 H13 N3 O2 S'
_chemical_formula_moiety         'C15 H13 N3 O2 S'
_chemical_formula_sum            'C15 H13 N3 O2 S'
_chemical_formula_weight         299.34
_chemical_name_systematic
;
N-(N-Benzoyl-hydrazinocarbothioyl)-benzamide
;
_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                 117.705(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7949(19)
_cell_length_b                   7.7004(10)
_cell_length_c                   13.9577(18)
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.6
_cell_volume                     1407.8(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.043
_diffrn_reflns_av_sigmaI/netI    0.080
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7907
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.8804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.097
_refine_ls_R_factor_gt           0.057
_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/[σ²(Fo²)+(0.0304P)²+0.1794P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.118
_refine_ls_wR_factor_ref         0.133
_reflns_number_gt                1925
_reflns_number_total             3097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6191.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2201947
_cod_database_fobs_code          2201947
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.19008(5) 0.07097(11) 0.41368(6) 0.0628(3) Uani d . 1 . . S
O1 0.49547(13) 0.1887(3) 0.43281(15) 0.0610(5) Uani d . 1 . . O
O2 0.30605(14) 0.0778(3) 0.13136(15) 0.0602(6) Uani d . 1 . . O
N1 0.37856(14) 0.1982(3) 0.49423(16) 0.0427(5) Uani d . 1 . . N
H1A 0.3677 0.2337 0.5464 0.051 Uiso calc R 1 . . H
N2 0.31213(15) 0.0790(3) 0.32451(17) 0.0474(6) Uani d . 1 . . N
H2A 0.3688 0.1062 0.3251 0.057 Uiso calc R 1 . . H
N3 0.23692(16) -0.0041(3) 0.23624(17) 0.0513(6) Uani d . 1 . . N
H3A 0.1896 -0.0601 0.2424 0.062 Uiso calc R 1 . . H
C1 0.54332(19) 0.3085(3) 0.7024(2) 0.0487(7) Uani d . 1 . . C
H1B 0.4880 0.2551 0.7049 0.058 Uiso calc R 1 . . H
C2 0.61817(19) 0.3866(4) 0.7941(2) 0.0519(7) Uani d . 1 . . C
H2B 0.6133 0.3848 0.8582 0.062 Uiso calc R 1 . . H
C3 0.6996(2) 0.4668(3) 0.7912(2) 0.0503(7) Uani d . 1 . . C
H3B 0.7492 0.5213 0.8527 0.060 Uiso calc R 1 . . H
C4 0.7076(2) 0.4663(4) 0.6969(2) 0.0542(7) Uani d . 1 . . C
H4A 0.7630 0.5202 0.6950 0.065 Uiso calc R 1 . . H
C5 0.63453(19) 0.3868(3) 0.6054(2) 0.0479(7) Uani d . 1 . . C
H5A 0.6414 0.3850 0.5425 0.057 Uiso calc R 1 . . H
C6 0.55034(17) 0.3092(3) 0.6068(2) 0.0398(6) Uani d . 1 . . C
C7 0.47454(18) 0.2282(3) 0.5049(2) 0.0430(6) Uani d . 1 . . C
C8 0.29731(18) 0.1172(3) 0.4087(2) 0.0420(6) Uani d . 1 . . C
C9 0.23762(19) 0.0024(3) 0.1402(2) 0.0432(6) Uani d . 1 . . C
C10 0.15052(18) -0.0874(3) 0.0494(2) 0.0410(6) Uani d . 1 . . C
C11 0.1361(2) -0.0548(4) -0.0539(2) 0.0554(7) Uani d . 1 . . C
H11A 0.1808 0.0186 -0.0642 0.067 Uiso calc R 1 . . H
C12 0.0556(2) -0.1308(4) -0.1423(2) 0.0662(9) Uani d . 1 . . C
H12A 0.0465 -0.1087 -0.2118 0.079 Uiso calc R 1 . . H
C13 -0.0104(2) -0.2379(4) -0.1279(3) 0.0605(8) Uani d . 1 . . C
H13A -0.0646 -0.2883 -0.1875 0.073 Uiso calc R 1 . . H
C14 0.0029(2) -0.2711(4) -0.0262(3) 0.0599(8) Uani d . 1 . . C
H14A -0.0423 -0.3442 -0.0166 0.072 Uiso calc R 1 . . H
C15 0.0835(2) -0.1964(3) 0.0630(2) 0.0531(7) Uani d . 1 . . C
H15A 0.0924 -0.2199 0.1322 0.064 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
C7 N1 C8 127.3(2) yes
C7 N1 H1A 116.4 ?
C8 N1 H1A 116.4 ?
C8 N2 N3 120.0(2) ?
C8 N2 H2A 120.0 ?
N3 N2 H2A 120.0 ?
C9 N3 N2 119.8(2) yes
C9 N3 H3A 120.1 ?
N2 N3 H3A 120.1 ?
C2 C1 C6 120.2(2) ?
C2 C1 H1B 119.9 ?
C6 C1 H1B 119.9 ?
C3 C2 C1 120.4(2) ?
C3 C2 H2B 119.8 ?
C1 C2 H2B 119.8 ?
C2 C3 C4 119.7(2) ?
C2 C3 H3B 120.2 ?
C4 C3 H3B 120.2 ?
C5 C4 C3 120.6(2) ?
C5 C4 H4A 119.7 ?
C3 C4 H4A 119.7 ?
C4 C5 C6 120.1(2) ?
C4 C5 H5A 120.0 ?
C6 C5 H5A 120.0 ?
C1 C6 C5 119.0(2) ?
C1 C6 C7 124.2(2) ?
C5 C6 C7 116.8(2) ?
O1 C7 N1 120.9(2) ?
O1 C7 C6 121.9(2) ?
N1 C7 C6 117.2(2) ?
N2 C8 N1 115.4(2) yes
N2 C8 S1 123.08(19) ?
N1 C8 S1 121.54(19) ?
O2 C9 N3 120.6(2) ?
O2 C9 C10 124.2(2) ?
N3 C9 C10 115.2(2) ?
C15 C10 C11 119.0(2) ?
C15 C10 C9 123.8(2) ?
C11 C10 C9 117.2(2) ?
C10 C11 C12 120.4(3) ?
C10 C11 H11A 119.8 ?
C12 C11 H11A 119.8 ?
C13 C12 C11 120.2(3) ?
C13 C12 H12A 119.9 ?
C11 C12 H12A 119.9 ?
C12 C13 C14 120.0(3) ?
C12 C13 H13A 120.0 ?
C14 C13 H13A 120.0 ?
C13 C14 C15 120.3(3) ?
C13 C14 H14A 119.8 ?
C15 C14 H14A 119.8 ?
C10 C15 C14 120.1(3) ?
C10 C15 H15A 119.9 ?
C14 C15 H15A 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.659(3) yes
O1 C7 . 1.221(3) yes
O2 C9 . 1.222(3) yes
N1 C7 . 1.376(3) yes
N1 C8 . 1.388(3) yes
N1 H1A . 0.8600 ?
N2 C8 . 1.324(3) yes
N2 N3 . 1.375(3) yes
N2 H2A . 0.8600 ?
N3 C9 . 1.346(3) yes
N3 H3A . 0.8600 ?
C1 C2 . 1.381(3) ?
C1 C6 . 1.385(3) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.371(3) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.376(4) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.375(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.390(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.479(3) ?
C9 C10 . 1.493(3) ?
C10 C15 . 1.378(3) ?
C10 C11 . 1.379(4) ?
C11 C12 . 1.385(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.362(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.364(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.387(4) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
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 O1 1_555 0.86 1.88 2.558(3) 134 yes
N3 H3A S1 1_555 0.86 2.59 2.923(2) 104 yes
N1 H1A O2 4_566 0.86 2.31 3.114(3) 155 yes
C2 H2B O1 4_566 0.93 2.47 3.263(4) 142 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3678664
