#------------------------------------------------------------------------------
#$Date: 2020-08-01 08:04:11 +0300 (Sat, 01 Aug 2020) $
#$Revision: 254731 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/35/2243520.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_2243520
loop_
_publ_author_name
'Medjroubi, Mohamed Larbi'
'Boudjada, Ali'
'Hamdouni, Noudjoud'
'Brihi, Ouarda'
'Jeannin, Olivier'
'Meinnel, Jean'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 2,6-diiodo-4-nitrotoluene and 2,4,6-tribromotoluene
;
_journal_coeditor_code           DJ2011
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1391
_journal_page_last               1397
_journal_paper_doi               10.1107/S2056989020010270
_journal_volume                  76
_journal_year                    2020
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C7 H5 Br3'
_chemical_formula_moiety         'C7 H5 Br3'
_chemical_formula_sum            'C7 H5 Br3'
_chemical_formula_weight         328.84
_chemical_name_systematic
;
2,4,6-Tribromotoluene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 110.519(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3484(11)
_cell_length_b                   3.9955(3)
_cell_length_c                   15.6975(12)
_cell_measurement_reflns_used    2989
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.38
_cell_volume                     842.83(11)
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2004 (Burla et al.,  2005)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6197
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.385
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.277
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.679
_refine_ls_extinction_coef       0.00060(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0154P)²+1.1776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0489
_reflns_number_gt                1657
_reflns_number_total             1928
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dj2011sup1.cif
_cod_data_source_block           TBT
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243520
_shelx_estimated_absorpt_t_min   0.085
_shelx_estimated_absorpt_t_max   0.279
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.68701(2) 1.18762(9) 0.84471(2) 0.02351(10) Uani d 1 . .
Br Br2 0.36077(2) 0.60522(9) 0.90955(2) 0.02044(10) Uani d 1 . .
Br Br3 0.35213(2) 0.68698(9) 0.55023(2) 0.02088(10) Uani d 1 . .
C C1 0.5156(2) 0.9306(8) 0.7029(2) 0.0151(7) Uani d 1 . .
C C2 0.5592(2) 0.9823(8) 0.7965(2) 0.0165(7) Uani d 1 . .
C C3 0.5158(2) 0.8920(8) 0.8588(2) 0.0167(7) Uani d 1 . .
H H3 0.548214 0.934507 0.921902 0.020 Uiso calc 1 . .
C C4 0.4234(2) 0.7369(8) 0.8266(2) 0.0154(7) Uani d 1 . .
C C5 0.3755(2) 0.6790(8) 0.7351(2) 0.0148(7) Uani d 1 . .
H H5 0.312062 0.574516 0.713540 0.018 Uiso calc 1 . .
C C6 0.4217(2) 0.7759(8) 0.6756(2) 0.0156(7) Uani d 1 . .
C C7 0.5638(2) 1.0280(9) 0.6357(2) 0.0219(8) Uani d 1 . .
H H7A 0.576650 0.826805 0.605878 0.033 Uiso calc 1 . .
H H7B 0.626764 1.142988 0.667500 0.033 Uiso calc 1 . .
H H7C 0.519404 1.177907 0.589887 0.033 Uiso calc 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 114.5(3) ?
C2 C1 C7 . . 123.6(3) ?
C6 C1 C7 . . 121.9(3) ?
C3 C2 C1 . . 124.1(3) ?
C3 C2 Br1 . . 116.2(2) ?
C1 C2 Br1 . . 119.7(2) ?
C2 C3 C4 . . 118.0(3) ?
C2 C3 H3 . . 121.0 ?
C4 C3 H3 . . 121.0 ?
C5 C4 C3 . . 121.2(3) ?
C5 C4 Br2 . . 119.1(2) ?
C3 C4 Br2 . . 119.7(2) ?
C6 C5 C4 . . 118.5(3) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.7 ?
C5 C6 C1 . . 123.7(3) ?
C5 C6 Br3 . . 116.5(2) ?
C1 C6 Br3 . . 119.8(2) ?
C1 C7 H7A . . 109.5 ?
C1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
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
Br1 C2 . 1.907(3) ?
Br2 C4 . 1.898(3) ?
Br3 C6 . 1.903(3) ?
C1 C2 . 1.396(4) ?
C1 C6 . 1.405(4) ?
C1 C7 . 1.502(4) ?
C2 C3 . 1.379(5) ?
C3 C4 . 1.389(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.377(4) ?
C5 C6 . 1.376(5) ?
C5 H5 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.0(5) ?
C7 C1 C2 C3 . . . . -179.6(3) ?
C6 C1 C2 Br1 . . . . 179.7(2) ?
C7 C1 C2 Br1 . . . . 0.1(5) ?
C1 C2 C3 C4 . . . . 0.7(5) ?
Br1 C2 C3 C4 . . . . -179.0(2) ?
C2 C3 C4 C5 . . . . -0.9(5) ?
C2 C3 C4 Br2 . . . . 179.7(2) ?
C3 C4 C5 C6 . . . . 0.5(5) ?
Br2 C4 C5 C6 . . . . 179.9(2) ?
C4 C5 C6 C1 . . . . 0.2(5) ?
C4 C5 C6 Br3 . . . . 179.7(2) ?
C2 C1 C6 C5 . . . . -0.5(5) ?
C7 C1 C6 C5 . . . . 179.2(3) ?
C2 C1 C6 Br3 . . . . -179.9(2) ?
C7 C1 C6 Br3 . . . . -0.3(4) ?

_cod_database_fobs_code 2243520
