#------------------------------------------------------------------------------
#$Date: 2016-05-14 04:46:03 +0300 (Sat, 14 May 2016) $
#$Revision: 182951 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/33/1543320.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1543320
loop_
_publ_author_name
'Bourichi, Selma'
'Kandri Rodi, Youssef'
'Ouzidan, Younes'
'Mague, Joel T.'
'Essassi, El Mokhtar'
'Zouihri, Hafid'
_publ_section_title
;
 6-Bromo-2-(4-chlorophenyl)-3-methyl-3H-imidazo[4,5-b]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-3H-imidazo[4,5-b]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
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT  (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       'ω 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
;
(SADABS; 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0357P)²+1.6642P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            bt4009sup1.cif
_cod_data_source_block           I
_cod_database_code               1543320
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.274
_shelx_estimated_absorpt_t_max   0.521
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.74454(2) 0.96264(2) 0.62272(2) 0.02958(10) Uani d 1
Cl Cl1 0.49454(6) 0.15942(7) 0.21428(3) 0.05102(19) Uani d 1
N N1 0.90119(14) 0.69452(18) 0.50012(8) 0.0259(4) Uani d 1
N N2 0.81367(14) 0.54647(17) 0.42228(8) 0.0233(4) Uani d 1
N N3 0.63564(13) 0.60528(18) 0.43957(8) 0.0255(4) Uani d 1
C C1 0.70284(17) 0.6795(2) 0.47964(10) 0.0235(4) Uani d 1
C C2 0.67830(17) 0.7774(2) 0.52549(10) 0.0244(4) Uani d 1
H H2 0.6049 0.8058 0.5342 0.029 Uiso calc 1
C C3 0.76839(16) 0.8304(2) 0.55755(10) 0.0246(4) Uani d 1
C C4 0.87671(17) 0.7888(2) 0.54435(10) 0.0265(4) Uani d 1
H H4 0.9354 0.8293 0.5678 0.032 Uiso calc 1
C C5 0.81385(16) 0.6445(2) 0.46971(9) 0.0232(4) Uani d 1
C C6 0.91170(17) 0.4733(2) 0.40010(11) 0.0283(4) Uani d 1
H H6A 0.9390 0.5157 0.3608 0.042 Uiso calc 1
H H6B 0.8926 0.3777 0.3917 0.042 Uiso calc 1
H H6C 0.9691 0.4774 0.4330 0.042 Uiso calc 1
C C7 0.70395(17) 0.5267(2) 0.40658(10) 0.0244(4) Uani d 1
C C8 0.66153(17) 0.4291(2) 0.35938(10) 0.0248(4) Uani d 1
C C9 0.71738(19) 0.3912(2) 0.30403(11) 0.0321(5) Uani d 1
H H9 0.7905 0.4228 0.2969 0.039 Uiso calc 1
C C10 0.6667(2) 0.3072(2) 0.25921(12) 0.0376(5) Uani d 1
H H10 0.7047 0.2815 0.2214 0.045 Uiso calc 1
C C11 0.55998(19) 0.2614(2) 0.27032(11) 0.0335(5) Uani d 1
C C12 0.50354(18) 0.2972(2) 0.32544(11) 0.0293(5) Uani d 1
H H12 0.4307 0.2647 0.3326 0.035 Uiso calc 1
C C13 0.55415(17) 0.3804(2) 0.36966(10) 0.0264(4) Uani d 1
H H13 0.5159 0.4051 0.4075 0.032 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C4 114.13(18)
C5 N2 C7 105.66(16)
C5 N2 C6 124.56(17)
C7 N2 C6 129.52(18)
C7 N3 C1 104.77(16)
N3 C1 C2 131.22(19)
N3 C1 C5 110.34(18)
C2 C1 C5 118.44(19)
C3 C2 C1 115.20(19)
C3 C2 H2 122.4
C1 C2 H2 122.4
C2 C3 C4 122.31(19)
C2 C3 Br1 118.93(15)
C4 C3 Br1 118.75(15)
N1 C4 C3 122.90(19)
N1 C4 H4 118.6
C3 C4 H4 118.6
N1 C5 N2 127.03(18)
N1 C5 C1 127.02(19)
N2 C5 C1 105.94(17)
N2 C6 H6A 109.5
N2 C6 H6B 109.5
H6A C6 H6B 109.5
N2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N3 C7 N2 113.28(18)
N3 C7 C8 120.71(18)
N2 C7 C8 126.01(19)
C9 C8 C13 119.2(2)
C9 C8 C7 124.34(19)
C13 C8 C7 116.28(19)
C10 C9 C8 120.3(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 119.3(2)
C11 C10 H10 120.4
C9 C10 H10 120.4
C12 C11 C10 121.1(2)
C12 C11 Cl1 118.94(17)
C10 C11 Cl1 119.92(19)
C13 C12 C11 119.3(2)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C8 120.7(2)
C12 C13 H13 119.6
C8 C13 H13 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.903(2)
Cl1 C11 1.733(2)
N1 C5 1.329(3)
N1 C4 1.341(3)
N2 C5 1.381(3)
N2 C7 1.383(3)
N2 C6 1.463(3)
N3 C7 1.325(3)
N3 C1 1.377(3)
C1 C2 1.389(3)
C1 C5 1.404(3)
C2 C3 1.383(3)
C2 H2 0.9500
C3 C4 1.402(3)
C4 H4 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.468(3)
C8 C9 1.393(3)
C8 C13 1.402(3)
C9 C10 1.391(3)
C9 H9 0.9500
C10 C11 1.388(3)
C10 H10 0.9500
C11 C12 1.387(3)
C12 C13 1.378(3)
C12 H12 0.9500
C13 H13 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4 N3 4_566 0.95 2.51 3.321(3) 143
C2 H2 N1 4_466 0.95 2.57 3.411(3) 148
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N3 C1 C2 -179.5(2)
C7 N3 C1 C5 0.4(2)
N3 C1 C2 C3 179.4(2)
C5 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 0.4(3)
C1 C2 C3 Br1 -178.73(15)
C5 N1 C4 C3 0.3(3)
C2 C3 C4 N1 -0.4(3)
Br1 C3 C4 N1 178.78(16)
C4 N1 C5 N2 -179.77(19)
C4 N1 C5 C1 -0.4(3)
C7 N2 C5 N1 178.96(19)
C6 N2 C5 N1 4.3(3)
C7 N2 C5 C1 -0.5(2)
C6 N2 C5 C1 -175.13(18)
N3 C1 C5 N1 -179.42(19)
C2 C1 C5 N1 0.5(3)
N3 C1 C5 N2 0.1(2)
C2 C1 C5 N2 179.97(18)
C1 N3 C7 N2 -0.8(2)
C1 N3 C7 C8 178.44(19)
C5 N2 C7 N3 0.8(2)
C6 N2 C7 N3 175.10(19)
C5 N2 C7 C8 -178.35(19)
C6 N2 C7 C8 -4.1(3)
N3 C7 C8 C9 148.4(2)
N2 C7 C8 C9 -32.5(3)
N3 C7 C8 C13 -26.8(3)
N2 C7 C8 C13 152.37(19)
C13 C8 C9 C10 0.7(3)
C7 C8 C9 C10 -174.3(2)
C8 C9 C10 C11 -0.2(4)
C9 C10 C11 C12 -0.4(4)
C9 C10 C11 Cl1 178.75(19)
C10 C11 C12 C13 0.4(4)
Cl1 C11 C12 C13 -178.75(17)
C11 C12 C13 C8 0.1(3)
C9 C8 C13 C12 -0.7(3)
C7 C8 C13 C12 174.72(19)

_cod_database_fobs_code 1543320
