#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/86/2018646.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_2018646
loop_
_publ_author_name
'Szczesio, Małgorzata'
'Olczak, Andrzej'
'Gobis, Katarzyna'
'Foks, Henryk'
'Główka, Marek L.'
_publ_section_title
;
 Planarity of benzoylhydrazine--dithiocarbazoate tuberculostatics. I.
 N'-Methyl-substituted 3,4-dichlorobenzoyl monoesters
;
_journal_coeditor_code           OV3016
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o373
_journal_page_last               o376
_journal_paper_doi               10.1107/S0108270112036001
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H10 Cl2 N2 O S2'
_chemical_formula_moiety         'C10 H10 Cl2 N2 O S2'
_chemical_formula_sum            'C10 H10 Cl2 N2 O S2'
_chemical_formula_weight         309.22
_chemical_name_systematic
;
Methyl 2-(3,4-dichlorobenzoyl)-1-methylhydrazinecarbodithioate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5696(3)
_cell_length_b                   24.7384(17)
_cell_length_c                   11.7638(8)
_cell_measurement_reflns_used    7396
_cell_measurement_temperature    292
_cell_measurement_theta_max      30.5165
_cell_measurement_theta_min      2.3985
_cell_volume                     1320.09(15)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008a)'
_diffrn_ambient_temperature      292
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14761
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0337
_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)+(0.0399P)²+0.4951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                1947
_reflns_number_total             2337
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ov3016.cif
_cod_data_source_block           F1
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               2018646
_cod_database_fobs_code          2018646
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_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
_atom_site_symmetry_multiplicity
C C1 0.9525(5) 0.68563(9) 0.77226(19) 0.0417(5) Uani d . 1 1
C C2 0.7006(7) 0.69895(11) 0.5760(2) 0.0668(8) Uani d . 1 1
H H2A 0.8355 0.6878 0.5239 0.100 Uiso calc R 1 1
H H2B 0.7237 0.7370 0.5910 0.100 Uiso calc R 1 1
H H2C 0.5022 0.6918 0.5426 0.100 Uiso calc R 1 1
C C4 0.7933(4) 0.57437(9) 0.65656(17) 0.0363(5) Uani d . 1 1
C C11 1.2264(7) 0.67130(13) 0.9941(2) 0.0738(8) Uani d . 1 1
H H11A 1.1410 0.7048 1.0151 0.111 Uiso calc R 1 1
H H11B 1.4107 0.6784 0.9656 0.111 Uiso calc R 1 1
H H11C 1.2592 0.6483 1.0601 0.111 Uiso calc R 1 1
C C41 0.6652(4) 0.52118(8) 0.68073(17) 0.0350(5) Uani d . 1 1
C C42 0.7192(5) 0.47715(9) 0.61316(19) 0.0423(5) Uani d . 1 1
H H42 0.8335 0.4815 0.5535 0.051 Uiso calc R 1 1
C C43 0.6057(5) 0.42733(9) 0.6335(2) 0.0465(5) Uani d . 1 1
H H43 0.6418 0.3982 0.5872 0.056 Uiso calc R 1 1
C C44 0.4382(5) 0.42015(9) 0.72222(19) 0.0428(5) Uani d . 1 1
C C45 0.3909(5) 0.46361(9) 0.79256(18) 0.0400(5) Uani d . 1 1
C C46 0.5022(4) 0.51392(9) 0.77104(18) 0.0380(5) Uani d . 1 1
H H46 0.4674 0.5430 0.8175 0.046 Uiso calc R 1 1
Cl Cl4 0.28831(16) 0.35746(2) 0.74307(6) 0.0628(2) Uani d . 1 1
Cl Cl5 0.19399(15) 0.45590(3) 0.90798(6) 0.0623(2) Uani d . 1 1
N N2 0.7621(4) 0.66912(7) 0.68263(16) 0.0438(4) Uani d . 1 1
N N3 0.6401(4) 0.61809(7) 0.68698(17) 0.0434(4) Uani d . 1 1
H H3 0.4684 0.6140 0.7088 0.052 Uiso calc R 1 1
O O4 1.0253(3) 0.57952(6) 0.61597(14) 0.0464(4) Uani d . 1 1
S S1 0.98179(16) 0.63880(3) 0.88581(5) 0.0550(2) Uani d . 1 1
S S2 1.13835(16) 0.74260(3) 0.77344(7) 0.0649(2) Uani d . 1 1
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'
Cl Cl 0.1484 0.1585 '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
N2 C1 S2 123.40(17)
N2 C1 S1 112.16(16)
S2 C1 S1 124.43(14)
N2 C2 H2A 109.5
N2 C2 H2B 109.5
H2A C2 H2B 109.5
N2 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
O4 C4 N3 121.27(19)
O4 C4 C41 123.34(19)
N3 C4 C41 115.33(18)
S1 C11 H11A 109.5
S1 C11 H11B 109.5
H11A C11 H11B 109.5
S1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C46 C41 C42 119.2(2)
C46 C41 C4 121.70(19)
C42 C41 C4 119.03(19)
C43 C42 C41 120.6(2)
C43 C42 H42 119.7
C41 C42 H42 119.7
C42 C43 C44 120.3(2)
C42 C43 H43 119.8
C44 C43 H43 119.8
C43 C44 C45 119.5(2)
C43 C44 Cl4 119.34(18)
C45 C44 Cl4 121.20(18)
C46 C45 C44 120.1(2)
C46 C45 Cl5 118.84(17)
C44 C45 Cl5 121.06(17)
C45 C46 C41 120.2(2)
C45 C46 H46 119.9
C41 C46 H46 119.9
C1 N2 N3 118.21(18)
C1 N2 C2 124.1(2)
N3 N2 C2 117.30(19)
C4 N3 N2 119.57(17)
C4 N3 H3 120.2
N2 N3 H3 120.2
C1 S1 C11 103.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.347(3)
C1 S2 1.645(2)
C1 S1 1.761(2)
C2 N2 1.453(3)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C4 O4 1.221(2)
C4 N3 1.360(3)
C4 C41 1.482(3)
C11 S1 1.782(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C41 C46 1.381(3)
C41 C42 1.388(3)
C42 C43 1.369(3)
C42 H42 0.9300
C43 C44 1.378(3)
C43 H43 0.9300
C44 C45 1.389(3)
C44 Cl4 1.725(2)
C45 C46 1.379(3)
C45 Cl5 1.728(2)
C46 H46 0.9300
N2 N3 1.384(2)
N3 H3 0.8600
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
N3 H3 O4 1_455 0.86 2.34 2.989(2) 132.2
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
O4 C4 C41 C46 147.6(2)
N3 C4 C41 C46 -29.9(3)
O4 C4 C41 C42 -30.1(3)
N3 C4 C41 C42 152.4(2)
C46 C41 C42 C43 1.8(3)
C4 C41 C42 C43 179.62(19)
C41 C42 C43 C44 -0.6(3)
C42 C43 C44 C45 -1.4(3)
C42 C43 C44 Cl4 177.96(17)
C43 C44 C45 C46 2.3(3)
Cl4 C44 C45 C46 -177.12(16)
C43 C44 C45 Cl5 -177.58(17)
Cl4 C44 C45 Cl5 3.0(3)
C44 C45 C46 C41 -1.1(3)
Cl5 C45 C46 C41 178.80(16)
C42 C41 C46 C45 -1.0(3)
C4 C41 C46 C45 -178.72(19)
S2 C1 N2 N3 173.80(15)
S1 C1 N2 N3 -5.3(2)
S2 C1 N2 C2 0.9(3)
S1 C1 N2 C2 -178.19(19)
O4 C4 N3 N2 -6.4(3)
C41 C4 N3 N2 171.10(17)
C1 N2 N3 C4 -83.2(3)
C2 N2 N3 C4 90.2(3)
N2 C1 S1 C11 -177.00(18)
S2 C1 S1 C11 3.89(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654395
