#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/09/2210905.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_2210905
loop_
_publ_author_name
'Saeed, Aamer'
'Flörke, Ulrich'
_publ_section_title
;
 1-(4-Bromophenyl)-3-(4-methylbenzoyl)thiourea
;
_journal_coeditor_code           BT2207
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5036
_journal_page_last               o5037
_journal_paper_doi               10.1107/S1600536806042309
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H13 Br N2 O S'
_chemical_formula_moiety         'C15 H13 Br N2 O S'
_chemical_formula_sum            'C15 H13 Br N2 O S'
_chemical_formula_weight         349.24
_chemical_name_systematic
;
1-(4-Bromophenyl)-3-(4-methylbenzoyl)thiourea
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.263(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5281(3)
_cell_length_b                   17.1059(11)
_cell_length_c                   18.4277(12)
_cell_measurement_reflns_used    2782
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.38
_cell_volume                     1423.41(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14167
_diffrn_reflns_theta_full        28.07
_diffrn_reflns_theta_max         28.07
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  450
_diffrn_standards_number         2733
_exptl_absorpt_coefficient_mu    3.031
_exptl_absorpt_correction_T_max  0.7936
_exptl_absorpt_correction_T_min  0.3626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0335
_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)+(0.0392P)²+0.1059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                2825
_reflns_number_total             3426
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2207.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210905
_cod_database_fobs_code          2210905
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
Br Br1 0.04349(5) 0.178541(13) 0.183035(13) 0.02507(9) Uani d . 1
S S1 0.80669(16) 0.30213(4) -0.13832(4) 0.03221(17) Uani d . 1
O O1 1.1257(4) 0.04950(9) -0.13003(9) 0.0275(4) Uani d . 1
N N1 0.8094(4) 0.15986(10) -0.07318(10) 0.0195(4) Uani d . 1
H H1A 0.8827 0.1124 -0.0757 0.023 Uiso calc R 1
N N2 1.1017(4) 0.17612(10) -0.16884(11) 0.0207(4) Uani d . 1
H H2B 1.1787 0.2088 -0.1991 0.025 Uiso calc R 1
C C1 0.6160(5) 0.16959(13) -0.01733(12) 0.0193(5) Uani d . 1
C C2 0.5680(5) 0.10214(13) 0.02287(12) 0.0222(5) Uani d . 1
H H2A 0.6592 0.0544 0.0106 0.027 Uiso calc R 1
C C3 0.3886(5) 0.10423(13) 0.08047(13) 0.0231(5) Uani d . 1
H H3A 0.3534 0.0580 0.1071 0.028 Uiso calc R 1
C C4 0.2614(5) 0.17417(13) 0.09878(13) 0.0209(5) Uani d . 1
C C5 0.3018(5) 0.24087(14) 0.05848(13) 0.0232(5) Uani d . 1
H H5A 0.2075 0.2882 0.0708 0.028 Uiso calc R 1
C C6 0.4794(5) 0.23935(13) 0.00002(12) 0.0220(5) Uani d . 1
H H6A 0.5070 0.2853 -0.0277 0.026 Uiso calc R 1
C C7 0.9029(5) 0.20930(13) -0.12325(13) 0.0209(5) Uani d . 1
C C8 1.1950(5) 0.09980(13) -0.17345(12) 0.0205(5) Uani d . 1
C C9 1.3799(5) 0.08125(13) -0.23440(12) 0.0193(5) Uani d . 1
C C10 1.5097(5) 0.13797(13) -0.27684(13) 0.0227(5) Uani d . 1
H H10A 1.4867 0.1919 -0.2662 0.027 Uiso calc R 1
C C11 1.6708(5) 0.11544(14) -0.33403(13) 0.0241(5) Uani d . 1
H H11A 1.7584 0.1544 -0.3622 0.029 Uiso calc R 1
C C12 1.7081(5) 0.03721(14) -0.35146(13) 0.0239(5) Uani d . 1
C C13 1.5858(5) -0.01883(14) -0.30815(13) 0.0262(5) Uani d . 1
H H13A 1.6155 -0.0727 -0.3179 0.031 Uiso calc R 1
C C14 1.4214(5) 0.00261(13) -0.25105(13) 0.0236(5) Uani d . 1
H H14A 1.3357 -0.0367 -0.2228 0.028 Uiso calc R 1
C C15 1.8754(6) 0.01411(16) -0.41582(14) 0.0340(6) Uani d . 1
H H15A 2.0805 0.0325 -0.4084 0.051 Uiso calc R 1
H H15B 1.7810 0.0378 -0.4601 0.051 Uiso calc R 1
H H15C 1.8735 -0.0429 -0.4208 0.051 Uiso calc R 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'
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
_geom_angle_publ_flag
C7 N1 C1 132.21(19) y
C7 N1 H1A 113.9 ?
C1 N1 H1A 113.9 ?
C8 N2 C7 129.56(19) y
C8 N2 H2B 115.2 ?
C7 N2 H2B 115.2 ?
C6 C1 C2 119.8(2) ?
C6 C1 N1 125.4(2) ?
C2 C1 N1 114.79(19) ?
C3 C2 C1 120.6(2) ?
C3 C2 H2A 119.7 ?
C1 C2 H2A 119.7 ?
C4 C3 C2 119.3(2) ?
C4 C3 H3A 120.4 ?
C2 C3 H3A 120.4 ?
C3 C4 C5 120.7(2) ?
C3 C4 Br1 119.00(17) ?
C5 C4 Br1 120.26(17) ?
C4 C5 C6 120.5(2) ?
C4 C5 H5A 119.7 ?
C6 C5 H5A 119.7 ?
C5 C6 C1 119.1(2) ?
C5 C6 H6A 120.5 ?
C1 C6 H6A 120.5 ?
N1 C7 N2 114.05(19) y
N1 C7 S1 128.56(18) y
N2 C7 S1 117.37(17) y
O1 C8 N2 121.9(2) y
O1 C8 C9 121.9(2) y
N2 C8 C9 116.25(19) y
C14 C9 C10 118.4(2) ?
C14 C9 C8 117.7(2) ?
C10 C9 C8 123.9(2) ?
C11 C10 C9 120.0(2) ?
C11 C10 H10A 120.0 ?
C9 C10 H10A 120.0 ?
C10 C11 C12 121.7(2) ?
C10 C11 H11A 119.1 ?
C12 C11 H11A 119.1 ?
C13 C12 C11 118.1(2) ?
C13 C12 C15 121.1(2) ?
C11 C12 C15 120.8(2) ?
C14 C13 C12 121.0(2) ?
C14 C13 H13A 119.5 ?
C12 C13 H13A 119.5 ?
C13 C14 C9 120.8(2) ?
C13 C14 H14A 119.6 ?
C9 C14 H14A 119.6 ?
C12 C15 H15A 109.5 ?
C12 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C12 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 1.902(2) y
S1 C7 1.664(2) y
O1 C8 1.232(3) y
N1 C7 1.343(3) y
N1 C1 1.410(3) y
N1 H1A 0.8800 ?
N2 C8 1.377(3) y
N2 C7 1.397(3) y
N2 H2B 0.8800 ?
C1 C6 1.392(3) ?
C1 C2 1.397(3) ?
C2 C3 1.384(3) ?
C2 H2A 0.9500 ?
C3 C4 1.381(3) ?
C3 H3A 0.9500 ?
C4 C5 1.381(3) ?
C5 C6 1.392(3) ?
C5 H5A 0.9500 ?
C6 H6A 0.9500 ?
C8 C9 1.484(3) ?
C9 C14 1.396(3) ?
C9 C10 1.402(3) ?
C10 C11 1.381(3) ?
C10 H10A 0.9500 ?
C11 C12 1.389(3) ?
C11 H11A 0.9500 ?
C12 C13 1.389(3) ?
C12 C15 1.507(3) ?
C13 C14 1.383(3) ?
C13 H13A 0.9500 ?
C14 H14A 0.9500 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 0.9800 ?
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
N1 H1A O1 . 0.88 1.88 2.634(2) 142.6
N2 H2B Br1 4_665 0.88 2.93 3.6870(19) 144.7
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 C1 C6 -2.5(4)
C7 N1 C1 C2 178.4(2)
C6 C1 C2 C3 -0.8(3)
N1 C1 C2 C3 178.4(2)
C1 C2 C3 C4 -1.2(4)
C2 C3 C4 C5 2.6(4)
C2 C3 C4 Br1 -174.62(17)
C3 C4 C5 C6 -2.1(4)
Br1 C4 C5 C6 175.16(18)
C4 C5 C6 C1 0.0(4)
C2 C1 C6 C5 1.4(3)
N1 C1 C6 C5 -177.7(2)
C1 N1 C7 N2 179.1(2)
C1 N1 C7 S1 -2.5(4)
C8 N2 C7 N1 5.8(3)
C8 N2 C7 S1 -172.8(2)
C7 N2 C8 O1 -6.6(4)
C7 N2 C8 C9 172.4(2)
O1 C8 C9 C14 13.5(3)
N2 C8 C9 C14 -165.5(2)
O1 C8 C9 C10 -167.8(2)
N2 C8 C9 C10 13.2(3)
C14 C9 C10 C11 0.8(3)
C8 C9 C10 C11 -177.9(2)
C9 C10 C11 C12 0.3(4)
C10 C11 C12 C13 -2.0(4)
C10 C11 C12 C15 177.7(2)
C11 C12 C13 C14 2.5(3)
C15 C12 C13 C14 -177.1(2)
C12 C13 C14 C9 -1.5(4)
C10 C9 C14 C13 -0.2(3)
C8 C9 C14 C13 178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 603024
