Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chlorophenyl)-4<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
Bourichi, Selma; Kandri Rodi, Youssef; Hökelek, Tuncer; Haoudi, Amal; Renard, Catherine; Capet, Frédéric; Acta Crystallographica Section E 75 (2019) 43–48; doi:10.1107/S2056989018017322

data_2242787
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-allyl-6-bromo-2-(4-chlorophenyl)-4<i>H</i>-imidazo[4,5-<i>b</i>]pyridine
;
_journal_coeditor_code           IS5505
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              43
_journal_page_last               48
_journal_paper_doi               10.1107/S2056989018017322
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H11 Br Cl N3'
_chemical_formula_moiety         'C15 H11 Br Cl N3'
_chemical_formula_sum            'C15 H11 Br Cl N3'
_chemical_formula_weight         348.63
_chemical_name_systematic
;
4-Allyl-6-bromo-2-(4-chlorophenyl)-4<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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                95.739(3)
_cell_angle_beta                 98.880(3)
_cell_angle_gamma                94.979(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6218(5)
_cell_length_b                   8.5238(5)
_cell_length_c                   11.1093(7)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.41
_cell_volume                     705.66(8)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2015)
;
_computing_data_collection
;
<i>APEX2</i> (Bruker, 2015)
;
_computing_data_reduction
;
<i>APEX2</i> (Bruker, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
<i>SHELXL</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31084
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.521
_diffrn_reflns_theta_min         1.868
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.094
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.473
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0395P)^2^+0.2342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                3226
_reflns_number_total             4288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            is5505sup1.cif
_cod_data_source_block           I
_cod_database_code               2242787
_cod_database_fobs_code          2242787
_shelx_hkl_checksum              52006
_shelx_res_checksum              6904