Crystal structure and Hirshfeld surface analysis of 2,6-diiodo-4-nitrotoluene and 2,4,6-tribromotoluene
Medjroubi, Mohamed Larbi; Boudjada, Ali; Hamdouni, Noudjoud; Brihi, Ouarda; Jeannin, Olivier; Meinnel, Jean; Acta Crystallographica Section E 76 (2020) 1391–1397; doi:10.1107/S2056989020010270

data_2243520
_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 <i>et al.</i>,
2020)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2004 (Burla <i>et al.</i>,  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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0154P)^2^+1.1776P] where P=(Fo^2^+2Fc^2^)/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>2\s(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
_cod_database_fobs_code          2243520
_shelx_estimated_absorpt_t_min   0.085
_shelx_estimated_absorpt_t_max   0.279
_shelx_hkl_checksum              65861
_shelx_res_checksum              33330