Synthesis, crystal structure and Hirshfeld surface analysis of the ortho-rhom-bic polymorph of 4-bromo-<i>N</i>-(4-bromo-benzyl-idene)aniline.
Subashini, A.; Ramamurthi, K.; Ramesh Babu, R.; Philip, Reji; Stoeckli-Evans, Helen; Acta crystallographica. Section E, Crystallographic communications 79 (2023) 146–150; doi:10.1107/S2056989023001111

data_2312070
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of the
 ortho-rhom-bic polymorph of
 4-bromo-<i>N</i>-(4-bromo-benzyl-idene)aniline.
;
_journal_coeditor_code           HB8048
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              146
_journal_page_last               150
_journal_paper_doi               10.1107/S2056989023001111
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H9 Br2 N'
_chemical_formula_moiety         'C13 H9 Br2 N'
_chemical_formula_sum            'C13 H9 Br2 N'
_chemical_formula_weight         339.03
_chemical_name_common
;
4-Bromo-<i>N</i>-(4-bromobenzylidene)aniline
;
_chemical_name_systematic
;
(<i>E</i>)-<i>N</i>,1-Bis(4-bromophenyl)methanimine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.4096(19)
_cell_length_b                   7.3301(5)
_cell_length_c                   5.9135(3)
_cell_measurement_reflns_used    8006
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      1.49
_cell_volume                     1188.11(13)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2009)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
SHELXL-2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and
Publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL-2018/3(Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       '\f + \w scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11334
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.662
_diffrn_reflns_theta_min         1.486
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    6.792
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS; Spek, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.482
_refine_ls_extinction_coef       0.0018(2)
_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   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         1125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+1.2266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                911
_reflns_number_total             1125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8048sup1.cif
_cod_data_source_block           I
_cod_database_code               2312070
_shelx_hkl_checksum              25143
_shelx_res_checksum              4796
_cod_database_fobs_code 2312070