##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1829295'
_audit_creation_method     'SHELXL-2018/1'
_journal_date_recd_electronic     2018-03-08
_journal_date_accepted     2018-03-13
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618004261
_journal_coeditor_code     HB4216
_publ_contact_author_name     'Gamal A. El-Hiti'
_publ_contact_author_address
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
_publ_contact_author_email     'gelhiti@ksu.edu.sa'
_publ_contact_author_fax     '00966114693536'
_publ_contact_author_phone     '00966114693778'
_publ_section_title
;
5-Bromo-1-(4-bromophenyl)isatin
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'El-Hiti, Gamal A.' .
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
    'Smith, Keith' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
UK
;
    'Alamri, Mesfer' .
;
School of Biosciences,
Cardiff University,
Cardiff CF10 3AT,
UK
;
    'Morris, Ceri A.' .
;
School of Medicine,
Cardiff University,
Tenovus Building,
Heath Park,
Cardiff CF14 4XN,
UK
;
    'Kille, Peter' .
;
School of Biosciences,
Cardiff University,
Cardiff CF10 3AT,
UK
;
    'Kariuki, Benson M.' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
UK
;
_publ_section_synopsis
;
All of the atoms except the C---H groups in the bromobenene ring lie on a (010)
crystallographic mirror plane, with the benzene ring completed by reflection.
The dihedral angle between the ring systems is constrained to be 90° by
symmetry. In the crystal, molecules are linked by weak C---H...Br interactions
in the [100] direction and paired very weak C---H...O interactions to the same
acceptor in the [001] direction, generating (010) sheets.
;
_chemical_name_systematic
;
5-Bromo-1-(4-bromophenyl)-2,3-dihydro-1H-indole-2,3-dione
;
_chemical_name_common
;
5-Bromo-1-(4-bromophenyl)isatin
;
_chemical_formula_moiety     'C14 H7 Br2 N O2'
_chemical_formula_sum     'C14 H7 Br2 N O2'
_chemical_formula_iupac     'C14 H7 Br2 N O2'
_chemical_formula_weight     381.03
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n m a'
_space_group_name_Hall     '-P 2ac 2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z-1/2'
    'x, -y-1/2, z'
_cell_length_a     15.1160(14)
_cell_length_b     6.8728(6)
_cell_length_c     12.7492(11)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1324.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1378
_cell_measurement_theta_min     4.3230
_cell_measurement_theta_max     25.8140
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.293
_exptl_crystal_size_mid     0.239
_exptl_crystal_size_min     0.192
_exptl_crystal_density_diffrn     1.911
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     736
_exptl_absorpt_coefficient_mu     6.115
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_shelx_estimated_absorpt_T_min     0.267
_shelx_estimated_absorpt_T_max     0.386
_exptl_absorpt_correction_T_min     0.37666
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Agilent SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5624
_diffrn_reflns_av_R_equivalents     0.0412
_diffrn_reflns_theta_min     3.368
_diffrn_reflns_theta_max     29.988
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.865
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
All H atoms were placed in calculated positions and refined using a riding
model. C---H bonds were fixed at 0.93 Å and Uiso(H) set to
1.2Ueq(C).
;
_reflns_number_total     1801
_reflns_number_gt     1174
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0775
_refine_ls_R_factor_gt     0.0407
_refine_ls_wR_factor_gt     0.0789
_refine_ls_wR_factor_ref     0.0963
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     1801
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0277P)²+1.3530P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.532
_refine_diff_density_min     -0.594
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.0052(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft,
2001)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.5530(3) 0.250000 0.3519(4) 0.0438(12) Uani d 1 . .
    C C2 0.4652(3) 0.250000 0.3236(4) 0.0476(12) Uani d 1 . .
    H H2 0.448493 0.250000 0.253441 0.057 Uiso calc 1 . .
    C C3 0.4023(4) 0.250000 0.4030(4) 0.0501(13) Uani d 1 . .
    H H3 0.342467 0.250000 0.385924 0.060 Uiso calc 1 . .
    C C4 0.4276(3) 0.250000 0.5072(4) 0.0429(11) Uani d 1 . .
    C C5 0.5158(3) 0.250000 0.5361(4) 0.0433(12) Uani d 1 . .
    H H5 0.532555 0.250000 0.606269 0.052 Uiso calc 1 . .
    C C6 0.5780(3) 0.250000 0.4567(4) 0.0421(11) Uani d 1 . .
    C C7 0.6743(3) 0.250000 0.4607(4) 0.0480(12) Uani d 1 . .
    C C8 0.7050(4) 0.250000 0.3443(5) 0.0516(13) Uani d 1 . .
    C C9 0.6233(3) 0.250000 0.1732(4) 0.0469(12) Uani d 1 . .
    C C10 0.6218(4) 0.0790(6) 0.1197(3) 0.0771(14) Uani d 1 . .
    H H10 0.625054 -0.038212 0.155897 0.092 Uiso calc 1 . .
    C C11 0.6156(4) 0.0789(7) 0.0112(4) 0.0831(15) Uani d 1 . .
    H H11 0.613968 -0.037843 -0.025692 0.100 Uiso calc 1 . .
    C C12 0.6118(3) 0.250000 -0.0401(4) 0.0535(14) Uani d 1 . .
    N N1 0.6283(3) 0.250000 0.2857(3) 0.0484(10) Uani d 1 . .
    O O1 0.7242(2) 0.250000 0.5347(3) 0.0650(11) Uani d 1 . .
    O O2 0.7799(3) 0.250000 0.3124(3) 0.0666(11) Uani d 1 . .
    Br Br1 0.33910(4) 0.250000 0.61293(5) 0.0564(2) Uani d 1 . .
    Br Br2 0.60700(6) 0.250000 -0.18928(5) 0.0946(3) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    C1 C2 . 1.374(7) ?
    C1 C6 . 1.389(7) ?
    C1 N1 . 1.418(6) ?
    C2 C3 . 1.390(7) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.382(7) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.383(7) ?
    C4 Br1 . 1.899(5) ?
    C5 C6 . 1.381(7) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.457(7) ?
    C7 O1 . 1.208(6) ?
    C7 C8 . 1.554(8) ?
    C8 O2 . 1.203(6) ?
    C8 N1 . 1.379(7) ?
    C9 C10 8_565 1.359(5) ?
    C9 C10 . 1.359(5) ?
    C9 N1 . 1.436(6) ?
    C10 C11 . 1.386(6) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.347(5) ?
    C11 H11 . 0.9300 ?
    C12 Br2 . 1.904(6) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C6 . . 121.0(5) ?
    C2 C1 N1 . . 128.3(5) ?
    C6 C1 N1 . . 110.7(4) ?
    C1 C2 C3 . . 118.0(5) ?
    C1 C2 H2 . . 121.0 ?
    C3 C2 H2 . . 121.0 ?
    C4 C3 C2 . . 120.7(5) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 121.5(5) ?
    C3 C4 Br1 . . 119.2(4) ?
    C5 C4 Br1 . . 119.3(4) ?
    C6 C5 C4 . . 117.5(4) ?
    C6 C5 H5 . . 121.3 ?
    C4 C5 H5 . . 121.3 ?
    C5 C6 C1 . . 121.3(5) ?
    C5 C6 C7 . . 130.9(5) ?
    C1 C6 C7 . . 107.8(5) ?
    O1 C7 C6 . . 130.6(5) ?
    O1 C7 C8 . . 124.0(5) ?
    C6 C7 C8 . . 105.4(4) ?
    O2 C8 N1 . . 127.4(6) ?
    O2 C8 C7 . . 127.1(5) ?
    N1 C8 C7 . . 105.5(4) ?
    C10 C9 C10 8_565 . 119.7(5) ?
    C10 C9 N1 8_565 . 120.2(3) ?
    C10 C9 N1 . . 120.2(3) ?
    C9 C10 C11 . . 120.2(4) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C12 C11 C10 . . 119.1(4) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C11 C12 C11 8_565 . 121.7(6) ?
    C11 C12 Br2 8_565 . 119.1(3) ?
    C11 C12 Br2 . . 119.1(3) ?
    C8 N1 C1 . . 110.6(4) ?
    C8 N1 C9 . . 125.9(4) ?
    C1 N1 C9 . . 123.5(4) ?
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
    C2 H2 O2 6_556 0.93 2.68 3.296(6) 124 yes
    C3 H3 O2 6_556 0.93 2.70 3.312(7) 124 yes
    C5 H5 Br2 1_556 0.93 2.84 3.763(5) 173 yes
