#------------------------------------------------------------------------------
#$Date: 2019-03-01 11:51:38 +0200 (Fri, 01 Mar 2019) $
#$Revision: 213925 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/33/7153370.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153370
loop_
_publ_author_name
'Yella, Ramesh'
'Murru, Siva'
'Ali, Abdur Rezzak'
'Patel, Bhisma K.'
_publ_section_title
;
 Arylthioureas with bromine or its equivalents gives no 'Hugerschoff'
 reaction product.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3389
_journal_page_last               3393
_journal_paper_doi               10.1039/c003892j
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C22 H24 Cl2 N4 O2 S'
_chemical_formula_sum            'C22 H24 Cl2 N4 O2 S'
_chemical_formula_weight         479.42
_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                 90.02
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1161(6)
_cell_length_b                   11.1981(6)
_cell_length_c                   22.7023(13)
_cell_measurement_reflns_used    6178
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.85
_cell_measurement_theta_min      2.23
_cell_volume                     2317.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28642
_diffrn_reflns_theta_full        24.25
_diffrn_reflns_theta_max         24.25
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0396
_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/[σ²(Fo²)+(0.1000P)²+0.1173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                2603
_reflns_number_total             3718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c003892j.txt
_cod_data_source_block           5b
_cod_depositor_comments
;
  Moved the _audit_creation_method data item out of the loop.

  Antanas Vaitkus,
  2019-03-01

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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7153370
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.11748(8) 0.55428(6) 0.05620(3) 0.0684(3) Uani 1 1 d .
Cl2 Cl 0.04201(10) -0.15995(6) 0.09245(4) 0.0852(3) Uani 1 1 d .
Cl1 Cl 0.32772(10) 0.62306(9) 0.35023(3) 0.0971(3) Uani 1 1 d .
N1 N 0.4507(2) 0.44549(17) 0.11004(9) 0.0548(5) Uani 1 1 d .
N3 N 0.4092(2) 0.32033(16) 0.03126(8) 0.0504(5) Uani 1 1 d .
N2 N 0.2180(2) 0.34911(14) 0.09889(8) 0.0457(5) Uani 1 1 d .
C21 C 0.3643(3) 0.37815(19) 0.08080(10) 0.0458(6) Uani 1 1 d .
N4 N 0.0086(2) 0.42369(18) 0.14343(9) 0.0618(6) Uani 1 1 d .
C16 C 0.5648(3) 0.3154(2) 0.01746(12) 0.0612(7) Uani 1 1 d .
H5A H 0.6222 0.3197 0.0534 0.073 Uiso 1 1 calc R
H5B H 0.5917 0.3823 -0.0075 0.073 Uiso 1 1 calc R
C12 C 0.2648(3) 0.14004(19) 0.12107(11) 0.0544(6) Uani 1 1 d .
H6 H 0.3532 0.1620 0.1384 0.065 Uiso 1 1 calc R
C1 C 0.4142(3) 0.4853(2) 0.16708(10) 0.0523(6) Uani 1 1 d .
C22 C 0.1123(3) 0.44060(18) 0.10204(10) 0.0481(6) Uani 1 1 d .
C7 C 0.1731(3) 0.22636(19) 0.09745(10) 0.0469(6) Uani 1 1 d .
C8 C 0.0420(3) 0.1935(2) 0.07176(11) 0.0555(6) Uani 1 1 d .
H10 H -0.0183 0.2514 0.0552 0.067 Uiso 1 1 calc R
C9 C -0.0004(3) 0.0748(2) 0.07053(12) 0.0632(7) Uani 1 1 d .
H11 H -0.0894 0.0526 0.0538 0.076 Uiso 1 1 calc R
C2 C 0.4270(3) 0.4109(2) 0.21541(12) 0.0651(7) Uani 1 1 d .
H12 H 0.4530 0.3313 0.2100 0.078 Uiso 1 1 calc R
C6 C 0.3784(3) 0.6044(2) 0.17603(11) 0.0605(7) Uani 1 1 d .
H13 H 0.3733 0.6563 0.1441 0.073 Uiso 1 1 calc R
O1 O 0.5065(2) 0.18518(18) -0.06525(9) 0.0840(6) Uani 1 1 d .
C5 C 0.3502(3) 0.6460(2) 0.23218(13) 0.0664(7) Uani 1 1 d .
H15 H 0.3231 0.7251 0.2380 0.080 Uiso 1 1 calc R
C13 C 0.3163(3) 0.3057(2) -0.02109(11) 0.0594(7) Uani 1 1 d .
H16A H 0.3317 0.3718 -0.0480 0.071 Uiso 1 1 calc R
H16B H 0.2137 0.3050 -0.0097 0.071 Uiso 1 1 calc R
C14 C 0.3554(3) 0.1901(3) -0.05075(13) 0.0774(8) Uani 1 1 d .
H17A H 0.3314 0.1241 -0.0248 0.093 Uiso 1 1 calc R
H17B H 0.2976 0.1815 -0.0864 0.093 Uiso 1 1 calc R
C10 C 0.0919(3) -0.0101(2) 0.09460(12) 0.0610(7) Uani 1 1 d .
C3 C 0.4018(3) 0.4531(3) 0.27175(13) 0.0721(8) Uani 1 1 d .
H19 H 0.4113 0.4028 0.3041 0.086 Uiso 1 1 calc R
C4 C 0.3625(3) 0.5702(3) 0.27924(12) 0.0647(7) Uani 1 1 d .
C15 C 0.5945(3) 0.1996(3) -0.01396(14) 0.0771(8) Uani 1 1 d .
H21A H 0.6972 0.1966 -0.0251 0.093 Uiso 1 1 calc R
H21B H 0.5758 0.1338 0.0128 0.093 Uiso 1 1 calc R
C20 C 0.0236(4) 0.3479(3) 0.19554(12) 0.0783(9) Uani 1 1 d .
H22A H -0.0377 0.2777 0.1912 0.094 Uiso 1 1 calc R
H22B H 0.1246 0.3217 0.1992 0.094 Uiso 1 1 calc R
C17 C -0.1344(3) 0.4848(3) 0.14038(16) 0.0914(10) Uani 1 1 d .
H23A H -0.2105 0.4276 0.1307 0.110 Uiso 1 1 calc R
H23B H -0.1320 0.5449 0.1096 0.110 Uiso 1 1 calc R
C11 C 0.2244(3) 0.0213(2) 0.11876(12) 0.0619(7) Uani 1 1 d .
H24 H 0.2868 -0.0372 0.1335 0.074 Uiso 1 1 calc R
O2 O -0.1629(3) 0.4574(4) 0.24408(13) 0.1437(13) Uani 1 1 d .
C19 C -0.0192(4) 0.4130(4) 0.24850(16) 0.1257(15) Uani 1 1 d .
H26A H -0.0125 0.3602 0.2823 0.151 Uiso 1 1 calc R
H26B H 0.0481 0.4789 0.2547 0.151 Uiso 1 1 calc R
C18 C -0.1682(5) 0.5423(4) 0.1978(2) 0.1342(17) Uani 1 1 d .
H27A H -0.0977 0.6054 0.2054 0.161 Uiso 1 1 calc R
H27B H -0.2651 0.5779 0.1962 0.161 Uiso 1 1 calc R
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
C21 N1 C1 121.22(19)
C21 N3 C16 119.32(19)
C21 N3 C13 123.26(19)
C16 N3 C13 112.59(19)
C22 N2 C21 119.09(17)
C22 N2 C7 120.22(18)
C21 N2 C7 118.44(17)
N1 C21 N3 121.7(2)
N1 C21 N2 124.0(2)
N3 C21 N2 114.14(19)
C22 N4 C20 125.5(2)
C22 N4 C17 121.5(2)
C20 N4 C17 113.0(2)
N3 C16 C15 108.1(2)
C11 C12 C7 119.7(2)
C2 C1 C6 118.9(2)
C2 C1 N1 121.3(2)
C6 C1 N1 119.6(2)
N4 C22 N2 114.43(19)
N4 C22 S1 124.79(17)
N2 C22 S1 120.75(17)
C8 C7 C12 120.0(2)
C8 C7 N2 120.8(2)
C12 C7 N2 119.2(2)
C7 C8 C9 120.4(2)
C10 C9 C8 118.9(2)
C1 C2 C3 120.9(2)
C5 C6 C1 120.2(3)
C14 O1 C15 110.7(2)
C4 C5 C6 119.7(3)
N3 C13 C14 108.8(2)
O1 C14 C13 111.6(2)
C11 C10 C9 121.2(2)
C11 C10 Cl2 119.2(2)
C9 C10 Cl2 119.6(2)
C4 C3 C2 119.1(3)
C5 C4 C3 121.2(3)
C5 C4 Cl1 119.7(2)
C3 C4 Cl1 119.1(2)
O1 C15 C16 112.6(2)
C19 C20 N4 110.6(3)
N4 C17 C18 110.1(3)
C10 C11 C12 119.8(2)
C19 O2 C18 108.8(3)
O2 C19 C20 111.6(3)
O2 C18 C17 110.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C22 1.645(2)
Cl2 C10 1.740(2)
Cl1 C4 1.746(3)
N1 C21 1.277(3)
N1 C1 1.409(3)
N3 C21 1.361(3)
N3 C16 1.454(3)
N3 C13 1.468(3)
N2 C22 1.408(3)
N2 C21 1.433(3)
N2 C7 1.434(3)
N4 C22 1.346(3)
N4 C20 1.462(3)
N4 C17 1.474(3)
C16 C15 1.505(4)
C12 C11 1.381(3)
C12 C7 1.386(3)
C1 C2 1.383(3)
C1 C6 1.388(3)
C7 C8 1.380(3)
C8 C9 1.384(3)
C9 C10 1.382(4)
C2 C3 1.383(4)
C6 C5 1.381(4)
O1 C14 1.417(3)
O1 C15 1.423(3)
C5 C4 1.369(4)
C13 C14 1.502(3)
C10 C11 1.372(4)
C3 C4 1.369(4)
C20 C19 1.459(4)
C17 C18 1.486(5)
O2 C19 1.405(4)
O2 C18 1.418(6)
