6-Bromo-2-(4-chlorophenyl)-3-methyl-3<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
Bourichi, Selma; Kandri Rodi, Youssef; Ouzidan, Younes; Mague, Joel T.; Essassi, El Mokhtar; Zouihri, Hafid; IUCrData 1 (2016) x160763–; doi:10.1107/S241431461600763X

data_1543320
_publ_section_title
;
 6-Bromo-2-(4-chlorophenyl)-3-methyl-3<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
;
_journal_coeditor_code           BT4009
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x160763
_journal_paper_doi               10.1107/S241431461600763X
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C13 H9 Br Cl N3'
_chemical_formula_moiety         'C13 H9 Br Cl N3'
_chemical_formula_sum            'C13 H9 Br Cl N3'
_chemical_formula_weight         322.59
_chemical_name_systematic
;
6-Bromo-2-(4-chlorophenyl)-3-methyl-3<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1163(2)
_cell_length_b                   9.7911(2)
_cell_length_c                   20.9428(4)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      72.4402
_cell_measurement_theta_min      4.2220
_cell_volume                     2484.48(8)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2015)
;
_computing_data_collection
;
<i>APEX2</i> (Bruker, 2015)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17929
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.511
_diffrn_reflns_theta_min         4.222
_exptl_absorpt_coefficient_mu    6.354
_exptl_absorpt_correction_T_max  0.52
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2015)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.442
_refine_ls_extinction_coef       0.00050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+1.6642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                2111
_reflns_number_total             2433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            bt4009sup1.cif
_cod_data_source_block           I
_cod_database_code               1543320
_cod_database_fobs_code          1543320
_shelx_estimated_absorpt_t_min   0.274
_shelx_estimated_absorpt_t_max   0.521
_shelx_hkl_checksum              48831
_shelx_res_checksum              62764