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#$Date: 2023-04-05 10:38:43 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107027.cif $
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#
# 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.
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data_8107027
loop_
_publ_author_name
'Ghabbour, Hazem A.'
'Kadi, Adnan A.'
'El-Subbagh, Hussein I.'
_publ_section_title
;
 Crystal structure of
 2-(4-(4-bromophenyl)thiazol-2-yl)isoindoline-1,3-dione, C17H9BrN2O2S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              853
_journal_page_last               854
_journal_paper_doi               10.1515/ncrs-2015-0291
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C17 H9 Br N2 O2 S'
_chemical_formula_weight         385.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4530(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2908(2)
_cell_length_b                   8.3281(2)
_cell_length_c                   16.1037(3)
_cell_measurement_reflns_used    5122
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.49
_cell_measurement_theta_min      2.75
_cell_volume                     1509.67(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean .
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10104
_diffrn_reflns_theta_full        69.90
_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         3.93
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.103
_exptl_absorpt_correction_T_max  0.7845
_exptl_absorpt_correction_T_min  0.2365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2009
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.002
_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+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                2577
_reflns_number_total             2809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0291_suppl.cif
_cod_data_source_block           A3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107027
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42712(2) 0.18105(3) 0.428732(16) 0.04870(16) Uani 1 1 d . . .
S1 S -0.21243(6) -0.38848(9) 0.38389(3) 0.0476(2) Uani 1 1 d . . .
O1 O -0.36028(16) -0.5734(2) 0.47113(10) 0.0457(4) Uani 1 1 d . . .
O2 O -0.06759(17) -0.3978(2) 0.66411(10) 0.0486(5) Uani 1 1 d . . .
N1 N -0.05185(19) -0.3016(2) 0.49678(11) 0.0332(4) Uani 1 1 d . . .
N2 N -0.19886(17) -0.4664(2) 0.54956(10) 0.0342(4) Uani 1 1 d . . .
C1 C 0.1540(2) -0.1072(3) 0.49777(13) 0.0357(5) Uani 1 1 d . . .
H1A H 0.1322 -0.1545 0.5466 0.043 Uiso 1 1 calc R . .
C2 C 0.2552(2) -0.0149(3) 0.49971(13) 0.0372(5) Uani 1 1 d . . .
H2A H 0.3014 0.0002 0.5495 0.045 Uiso 1 1 calc R . .
C3 C 0.2876(2) 0.0551(3) 0.42711(13) 0.0356(5) Uani 1 1 d . . .
C4 C 0.2186(2) 0.0343(3) 0.35296(13) 0.0416(5) Uani 1 1 d . . .
H4A H 0.2407 0.0824 0.3044 0.050 Uiso 1 1 calc R . .
C5 C 0.1175(2) -0.0575(3) 0.35132(13) 0.0404(5) Uani 1 1 d . . .
H5A H 0.0712 -0.0707 0.3015 0.049 Uiso 1 1 calc R . .
C6 C 0.08328(19) -0.1312(3) 0.42353(12) 0.0319(4) Uani 1 1 d . . .
C7 C -0.0236(2) -0.2325(3) 0.42300(13) 0.0333(5) Uani 1 1 d . . .
C8 C -0.0993(3) -0.2664(4) 0.35610(14) 0.0443(6) Uani 1 1 d . . .
C9 C -0.14725(19) -0.3845(3) 0.48532(12) 0.0320(4) Uani 1 1 d . . .
C10 C -0.3049(2) -0.5549(3) 0.53770(13) 0.0358(5) Uani 1 1 d . . .
C11 C -0.3311(2) -0.6153(3) 0.62084(13) 0.0392(5) Uani 1 1 d . . .
C12 C -0.4235(3) -0.7075(4) 0.64431(17) 0.0524(7) Uani 1 1 d . . .
H12A H -0.4852 -0.7383 0.6060 0.063 Uiso 1 1 calc R . .
C13 C -0.4215(3) -0.7530(4) 0.72736(19) 0.0623(8) Uani 1 1 d . . .
H13A H -0.4826 -0.8160 0.7452 0.075 Uiso 1 1 calc R . .
C14 C -0.3287(4) -0.7052(4) 0.78451(16) 0.0592(8) Uani 1 1 d . . .
H14A H -0.3288 -0.7377 0.8397 0.071 Uiso 1 1 calc R . .
C15 C -0.2372(3) -0.6111(3) 0.76067(15) 0.0516(7) Uani 1 1 d . . .
H15A H -0.1758 -0.5788 0.7988 0.062 Uiso 1 1 calc R . .
C16 C -0.2398(2) -0.5660(3) 0.67765(13) 0.0393(5) Uani 1 1 d . . .
C17 C -0.1547(2) -0.4666(3) 0.63541(12) 0.0359(5) Uani 1 1 d . . .
H8 H -0.086(4) -0.241(6) 0.300(3) 0.092(13) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C8 S1 C9 87.97(11) . .
C9 N1 C7 110.43(18) . .
C9 N2 C10 123.55(16) . .
C9 N2 C17 125.35(19) . .
C10 N2 C17 111.06(18) . .
C2 C1 C6 121.1(2) . .
C2 C1 H1A 119.4 . .
C6 C1 H1A 119.4 . .
C1 C2 C3 119.40(19) . .
C1 C2 H2A 120.3 . .
C3 C2 H2A 120.3 . .
C2 C3 C4 120.6(2) . .
C2 C3 Br1 119.84(16) . .
C4 C3 Br1 119.57(17) . .
C5 C4 C3 119.8(2) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
C4 C5 C6 120.83(19) . .
C4 C5 H5A 119.6 . .
C6 C5 H5A 119.6 . .
C5 C6 C1 118.2(2) . .
C5 C6 C7 121.80(19) . .
C1 C6 C7 120.01(19) . .
C8 C7 N1 115.1(2) . .
C8 C7 C6 126.3(2) . .
N1 C7 C6 118.58(18) . .
C7 C8 S1 110.67(18) . .
C7 C8 H8 125(3) . .
S1 C8 H8 124(3) . .
N1 C9 N2 123.27(18) . .
N1 C9 S1 115.82(16) . .
N2 C9 S1 120.90(16) . .
O1 C10 N2 124.3(2) . .
O1 C10 C11 129.3(2) . .
N2 C10 C11 106.44(18) . .
C12 C11 C16 121.8(2) . .
C12 C11 C10 130.4(2) . .
C16 C11 C10 107.8(2) . .
C11 C12 C13 117.5(3) . .
C11 C12 H12A 121.2 . .
C13 C12 H12A 121.2 . .
C12 C13 C14 120.8(3) . .
C12 C13 H13A 119.6 . .
C14 C13 H13A 119.6 . .
C15 C14 C13 121.3(3) . .
C15 C14 H14A 119.4 . .
C13 C14 H14A 119.4 . .
C14 C15 C16 117.6(3) . .
C14 C15 H15A 121.2 . .
C16 C15 H15A 121.2 . .
C15 C16 C11 121.0(2) . .
C15 C16 C17 129.1(2) . .
C11 C16 C17 109.87(19) . .
O2 C17 N2 125.8(2) . .
O2 C17 C16 129.4(2) . .
N2 C17 C16 104.80(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.891(2) .
S1 C8 1.718(3) .
S1 C9 1.7390(19) .
O1 C10 1.208(3) .
O2 C17 1.200(3) .
N1 C9 1.281(3) .
N1 C7 1.380(3) .
N2 C9 1.403(3) .
N2 C10 1.407(3) .
N2 C17 1.433(2) .
C1 C2 1.375(3) .
C1 C6 1.400(3) .
C1 H1A 0.9300 .
C2 C3 1.381(3) .
C2 H2A 0.9300 .
C3 C4 1.385(3) .
C4 C5 1.372(4) .
C4 H4A 0.9300 .
C5 C6 1.396(3) .
C5 H5A 0.9300 .
C6 C7 1.472(3) .
C7 C8 1.353(3) .
C8 H8 0.96(4) .
C10 C11 1.481(3) .
C11 C12 1.371(4) .
C11 C16 1.387(3) .
C12 C13 1.389(4) .
C12 H12A 0.9300 .
C13 C14 1.398(5) .
C13 H13A 0.9300 .
C14 C15 1.375(5) .
C14 H14A 0.9300 .
C15 C16 1.387(3) .
C15 H15A 0.9300 .
C16 C17 1.474(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.1(4) . . . .
C1 C2 C3 C4 0.6(4) . . . .
C1 C2 C3 Br1 -179.56(18) . . . .
C2 C3 C4 C5 -0.4(4) . . . .
Br1 C3 C4 C5 179.7(2) . . . .
C3 C4 C5 C6 -0.3(4) . . . .
C4 C5 C6 C1 0.8(4) . . . .
C4 C5 C6 C7 -178.9(2) . . . .
C2 C1 C6 C5 -0.6(4) . . . .
C2 C1 C6 C7 179.1(2) . . . .
C9 N1 C7 C8 -0.5(3) . . . .
C9 N1 C7 C6 179.6(2) . . . .
C5 C6 C7 C8 0.1(4) . . . .
C1 C6 C7 C8 -179.7(3) . . . .
C5 C6 C7 N1 179.9(2) . . . .
C1 C6 C7 N1 0.2(3) . . . .
N1 C7 C8 S1 0.4(3) . . . .
C6 C7 C8 S1 -179.72(19) . . . .
C9 S1 C8 C7 -0.2(2) . . . .
C7 N1 C9 N2 -178.8(2) . . . .
C7 N1 C9 S1 0.4(3) . . . .
C10 N2 C9 N1 178.7(2) . . . .
C17 N2 C9 N1 1.3(4) . . . .
C10 N2 C9 S1 -0.5(3) . . . .
C17 N2 C9 S1 -177.83(18) . . . .
C8 S1 C9 N1 -0.1(2) . . . .
C8 S1 C9 N2 179.1(2) . . . .
C9 N2 C10 O1 2.3(4) . . . .
C17 N2 C10 O1 179.9(2) . . . .
C9 N2 C10 C11 -177.4(2) . . . .
C17 N2 C10 C11 0.2(3) . . . .
O1 C10 C11 C12 0.3(5) . . . .
N2 C10 C11 C12 180.0(3) . . . .
O1 C10 C11 C16 178.5(3) . . . .
N2 C10 C11 C16 -1.8(3) . . . .
C16 C11 C12 C13 -1.3(4) . . . .
C10 C11 C12 C13 176.7(3) . . . .
C11 C12 C13 C14 0.4(5) . . . .
C12 C13 C14 C15 0.5(5) . . . .
C13 C14 C15 C16 -0.4(5) . . . .
C14 C15 C16 C11 -0.5(4) . . . .
C14 C15 C16 C17 179.9(3) . . . .
C12 C11 C16 C15 1.4(4) . . . .
C10 C11 C16 C15 -177.0(2) . . . .
C12 C11 C16 C17 -178.9(2) . . . .
C10 C11 C16 C17 2.7(3) . . . .
C9 N2 C17 O2 -0.5(4) . . . .
C10 N2 C17 O2 -178.1(2) . . . .
C9 N2 C17 C16 178.9(2) . . . .
C10 N2 C17 C16 1.3(3) . . . .
C15 C16 C17 O2 -3.4(5) . . . .
C11 C16 C17 O2 176.9(3) . . . .
C15 C16 C17 N2 177.2(3) . . . .
C11 C16 C17 N2 -2.5(3) . . . .
