π-stacking and C—<i>X</i>···<i>D</i> (<i>X</i> = H, NO~2~; <i>D</i> = O, π) interactions in the crystal network of both C—H···N and π-stacked dimers of 1,2-bis(4-bromophenyl)-1<i>H</i>-benzimidazole and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1<i>H</i>-benzimidazole
González-Padilla, Jazmin E.; Rosales-Hernández, Martha C.; Padilla-Martínez, Itzia I.; García-Báez, Efren V.; Rojas-Lima, Susana; Salazar-Pereda, Veronica; Acta Crystallographica Section C 70 (2014) 55–59; doi:10.1107/S2053229613033329

data_2019409
_publ_section_title
;
 \p-stacking and C---<i>X</i>&#x00B7;&#x00B7;&#x00B7;<i>D</i> (<i>X</i> =
 H, NO~2~; <i>D</i> = O, \p) interactions in the crystal network of both
 C---H&#x00B7;&#x00B7;&#x00B7;N and \p-stacked dimers of
 1,2-bis(4-bromophenyl)-1<i>H</i>-benzimidazole and
 2-(4-bromophenyl)-1-(4-nitrophenyl)-1<i>H</i>-benzimidazole
;
_journal_coeditor_code           FG3315
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              55
_journal_page_last               59
_journal_paper_doi               10.1107/S2053229613033329
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C19 H12 Br N3 O2'
_chemical_formula_moiety         'C19 H12 Br N3 O2'
_chemical_formula_sum            'C19 H12 Br N3 O2'
_chemical_formula_weight         394.23
_chemical_name_systematic
;
2-(4-Bromophenyl)-1-(4-nitrophenyl)-1<i>H</i>-benzimidazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                68.534(4)
_cell_angle_beta                 76.677(4)
_cell_angle_gamma                86.869(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8689(4)
_cell_length_b                   10.0444(4)
_cell_length_c                   11.8867(5)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     850.35(7)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), and WinGX2003 (Farrugia, 2012) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15531
_diffrn_reflns_theta_full        78.69
_diffrn_reflns_theta_max         78.69
_diffrn_reflns_theta_min         4.12
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.444
_exptl_absorpt_correction_T_max  0.5273
_exptl_absorpt_correction_T_min  0.4820
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   '(Dwiggins, 1975)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_size_rad          0.1500
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.642
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.2882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                3030
_reflns_number_total             3560
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3315sup1.cif
_cod_data_source_block           II
_cod_database_code               2019409
_cod_database_fobs_code          2019409