Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromohexyl)-2-[4-(dimethylamino)phenyl]-3<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
Jabri, Zainab; Sebbar, Nada Kheira; Hökelek, Tuncer; Mague, Joel T.; Sabir, Safia; Rodi, Youssef Kandri; Misbahi, Khalid; Acta Crystallographica Section E 76 (2020) 1234–1238; doi:10.1107/S2056989020008889

data_2243484
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT study of
 6-bromo-3-(5-bromohexyl)-2-[4-(dimethylamino)phenyl]-3<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
;
_journal_coeditor_code           WM5570
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1234
_journal_page_last               1238
_journal_paper_doi               10.1107/S2056989020008889
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C20 H24 Br2 N4'
_chemical_formula_moiety         'C20 H24 Br2 N4'
_chemical_formula_sum            'C20 H24 Br2 N4'
_chemical_formula_weight         480.25
_chemical_name_systematic
6-Bromo-3-(5-bromohexyl)-2-[4-(dimethylamino)phenyl]-3<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                64.049(2)
_cell_angle_beta                 74.184(2)
_cell_angle_gamma                86.067(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1488(11)
_cell_length_b                   11.2243(15)
_cell_length_c                   12.6378(17)
_cell_measurement_reflns_used    9203
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1379
_cell_measurement_theta_min      2.6023
_cell_volume                     998.3(2)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/1</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19397
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_min         1.861
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.072
_exptl_absorpt_correction_T_max  0.50
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.195
_refine_diff_density_max         2.183
_refine_diff_density_min         -0.805
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0785P)^2^+0.5344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                4168
_reflns_number_total             5325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5570sup1.cif
_cod_data_source_block           I
_cod_database_code               2243484
_cod_database_fobs_code          2243484
_shelx_estimated_absorpt_t_min   0.334
_shelx_estimated_absorpt_t_max   0.504
_shelx_hkl_checksum              79548
_shelx_res_checksum              89884