##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2016/6'
_journal_date_recd_electronic     2019-09-18
_journal_date_accepted     2019-09-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue     11
_journal_page_first     1620
_journal_page_last     1626
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019013410
_journal_coeditor_code     WM5525
_publ_contact_author_name     'Mahendra M'
_publ_contact_author_address
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysuru-570006
Karnataka
India
;
_publ_contact_author_email     'mahendra@physics.uni-mysore.ac.in'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '9964330328'
_publ_section_title
;
Crystal structure, DFT calculation, Hirshfeld surface analysis and energy
framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Khamees, Hussien Ahmed' .
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysuru 570 006
Karnataka
India
;
    'Chaluvaiah, Kumara' .
;
Department of Chemistry
Mangalore University
Mangalagangothri
Mangaluru 574 199
Karnataka
India
;
    'El-khatatneh, Nasseem Ahmed' .
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysuru 570 006
Karnataka
India
;
    'Swamynayaka, Ananda' .
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysuru 570 006
Karnataka
India
;
    'Chong, Kwong Huey' .
;
Department of Chemistry
Faculty of Science
Universiti Putra Malaysia 43400
UPM Serdang
Selangor Darul Ehsan,
Malaysia
;
    'Dasappa, Jagadeesh Prasad' .
;
Department of Chemistry
Mangalore University
Mangalagangothri
Mangaluru 574 199
Karnataka
India
;
    'Madegowda, Mahendra' .
;
Department of Studies in Physics
Manasagangotri
University of Mysore
Mysuru 570 006
Karnataka
India
;
_publ_section_synopsis
;
The molecular system displays a planar conformation between the phenyl and
imidazo[1,2-a] pyridine rings. Weak C---H...π and π--π interactions
as well as short contacts consolidate the three-dimensional network structure.
;
_chemical_name_systematic
;
6-Bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H8 Br2 N2'
_chemical_formula_sum     'C13 H8 Br2 N2'
_chemical_formula_iupac     'C13 H8 Br2 N2'
_chemical_formula_weight     352.03
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
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'
_cell_length_a     14.1711(4)
_cell_length_b     6.0546(2)
_cell_length_c     27.7102(8)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2377.54(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3485
_cell_measurement_theta_min     2.056
_cell_measurement_theta_max     30.046
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.150
_exptl_crystal_size_mid     0.140
_exptl_crystal_size_min     0.140
_exptl_crystal_density_diffrn     1.967
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1360
_exptl_absorpt_coefficient_mu     6.795
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     293(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'ω and φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     41143
_diffrn_reflns_av_R_equivalents     0.1002
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_theta_min     2.056
_diffrn_reflns_theta_max     30.046
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -39
_diffrn_reflns_limit_l_max     38
_refine_special_details     ?
_reflns_number_total     3485
_reflns_number_gt     1726
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1269
_refine_ls_R_factor_gt     0.0473
_refine_ls_wR_factor_gt     0.0939
_refine_ls_wR_factor_ref     0.1183
_refine_ls_goodness_of_fit_ref     0.996
_refine_ls_restrained_S_all     0.996
_refine_ls_number_reflns     3485
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0442P)²+2.6166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.880
_refine_diff_density_min     -0.489
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         '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' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br2 0.15325(4) 0.05914(9) 0.27691(2) 0.0700(2) Uani d 1 . .
    Br Br1 0.12673(4) 0.88905(10) 0.68410(2) 0.0740(2) Uani d 1 . .
    N N2 0.1377(2) 0.3517(6) 0.40975(12) 0.0449(8) Uani d 1 . .
    N N1 0.0885(2) 0.6735(6) 0.44091(12) 0.0484(9) Uani d 1 . .
    C C7 0.1238(3) 0.5400(6) 0.47646(14) 0.0401(9) Uani d 1 . .
    C C1 0.1234(3) 0.7762(8) 0.62067(15) 0.0482(11) Uani d 1 . .
    C C11 0.1297(3) 0.2554(7) 0.32808(15) 0.0498(11) Uani d 1 . .
    C C4 0.1241(3) 0.6173(7) 0.52687(15) 0.0424(9) Uani d 1 . .
    C C12 0.0872(3) 0.4597(8) 0.31737(16) 0.0571(12) Uani d 1 . .
    H H12 0.070603 0.493692 0.285760 0.069 Uiso calc 1 . .
    C C8 0.1549(3) 0.3438(8) 0.45819(15) 0.0479(10) Uani d 1 . .
    H H8 0.182324 0.228190 0.475266 0.058 Uiso calc 1 . .
    C C3 0.1597(3) 0.4933(7) 0.56424(16) 0.0495(10) Uani d 1 . .
    H H3 0.185335 0.355055 0.557750 0.059 Uiso calc 1 . .
    C C6 0.0866(3) 0.9064(7) 0.58414(16) 0.0539(11) Uani d 1 . .
    H H6 0.061410 1.044944 0.590752 0.065 Uiso calc 1 . .
    C C13 0.0707(3) 0.6058(8) 0.35300(15) 0.0561(12) Uani d 1 . .
    H H13 0.041977 0.740195 0.346048 0.067 Uiso calc 1 . .
    C C2 0.1582(3) 0.5687(8) 0.61068(16) 0.0532(11) Uani d 1 . .
    H H2 0.180652 0.480001 0.635558 0.064 Uiso calc 1 . .
    C C5 0.0885(3) 0.8244(7) 0.53745(15) 0.0479(10) Uani d 1 . .
    H H5 0.065063 0.911265 0.512485 0.057 Uiso calc 1 . .
    C C9 0.0968(3) 0.5559(7) 0.40055(15) 0.0442(10) Uani d 1 . .
    C C10 0.1555(3) 0.2005(7) 0.37352(15) 0.0492(11) Uani d 1 . .
    H H10 0.184202 0.065712 0.380142 0.059 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br2 C11 . 1.880(4) ?
    Br1 C1 . 1.886(4) ?
    N2 C8 . 1.365(5) ?
    N2 C10 . 1.382(5) ?
    N2 C9 . 1.389(5) ?
    N1 C9 . 1.331(5) ?
    N1 C7 . 1.369(5) ?
    C7 C8 . 1.364(6) ?
    C7 C4 . 1.473(6) ?
    C1 C2 . 1.378(6) ?
    C1 C6 . 1.385(6) ?
    C11 C10 . 1.353(6) ?
    C11 C12 . 1.407(6) ?
    C4 C3 . 1.375(6) ?
    C4 C5 . 1.383(6) ?
    C12 C13 . 1.346(6) ?
    C12 H12 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C3 C2 . 1.366(6) ?
    C3 H3 . 0.9300 ?
    C6 C5 . 1.386(6) ?
    C6 H6 . 0.9300 ?
    C13 C9 . 1.401(6) ?
    C13 H13 . 0.9300 ?
    C2 H2 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C10 H10 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C8 N2 C10 . . 131.2(4) ?
    C8 N2 C9 . . 106.6(3) ?
    C10 N2 C9 . . 122.2(4) ?
    C9 N1 C7 . . 104.8(3) ?
    C8 C7 N1 . . 111.4(4) ?
    C8 C7 C4 . . 128.9(4) ?
    N1 C7 C4 . . 119.7(4) ?
    C2 C1 C6 . . 120.5(4) ?
    C2 C1 Br1 . . 120.6(3) ?
    C6 C1 Br1 . . 119.0(4) ?
    C10 C11 C12 . . 121.9(4) ?
    C10 C11 Br2 . . 119.9(3) ?
    C12 C11 Br2 . . 118.2(3) ?
    C3 C4 C5 . . 118.0(4) ?
    C3 C4 C7 . . 122.8(4) ?
    C5 C4 C7 . . 119.2(4) ?
    C13 C12 C11 . . 119.8(4) ?
    C13 C12 H12 . . 120.1 ?
    C11 C12 H12 . . 120.1 ?
    C7 C8 N2 . . 106.1(4) ?
    C7 C8 H8 . . 127.0 ?
    N2 C8 H8 . . 127.0 ?
    C2 C3 C4 . . 121.4(4) ?
    C2 C3 H3 . . 119.3 ?
    C4 C3 H3 . . 119.3 ?
    C1 C6 C5 . . 118.1(4) ?
    C1 C6 H6 . . 120.9 ?
    C5 C6 H6 . . 120.9 ?
    C12 C13 C9 . . 120.1(4) ?
    C12 C13 H13 . . 119.9 ?
    C9 C13 H13 . . 119.9 ?
    C3 C2 C1 . . 120.0(4) ?
    C3 C2 H2 . . 120.0 ?
    C1 C2 H2 . . 120.0 ?
    C4 C5 C6 . . 122.0(4) ?
    C4 C5 H5 . . 119.0 ?
    C6 C5 H5 . . 119.0 ?
    N1 C9 N2 . . 111.0(3) ?
    N1 C9 C13 . . 130.6(4) ?
    N2 C9 C13 . . 118.3(4) ?
    C11 C10 N2 . . 117.6(4) ?
    C11 C10 H10 . . 121.2 ?
    N2 C10 H10 . . 121.2 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C9 N1 C7 C8 . . . . 0.9(5) ?
    C9 N1 C7 C4 . . . . -178.9(4) ?
    C8 C7 C4 C3 . . . . 1.1(6) ?
    N1 C7 C4 C3 . . . . -179.1(4) ?
    C8 C7 C4 C5 . . . . -179.8(4) ?
    N1 C7 C4 C5 . . . . 0.0(6) ?
    C10 C11 C12 C13 . . . . -0.5(7) ?
    Br2 C11 C12 C13 . . . . -178.9(4) ?
    N1 C7 C8 N2 . . . . -0.8(5) ?
    C4 C7 C8 N2 . . . . 179.0(4) ?
    C10 N2 C8 C7 . . . . 179.3(4) ?
    C9 N2 C8 C7 . . . . 0.3(4) ?
    C5 C4 C3 C2 . . . . 1.5(6) ?
    C7 C4 C3 C2 . . . . -179.4(4) ?
    C2 C1 C6 C5 . . . . -1.8(6) ?
    Br1 C1 C6 C5 . . . . 177.3(3) ?
    C11 C12 C13 C9 . . . . 0.8(7) ?
    C4 C3 C2 C1 . . . . -2.2(7) ?
    C6 C1 C2 C3 . . . . 2.4(7) ?
    Br1 C1 C2 C3 . . . . -176.7(3) ?
    C3 C4 C5 C6 . . . . -1.0(6) ?
    C7 C4 C5 C6 . . . . 179.9(4) ?
    C1 C6 C5 C4 . . . . 1.2(6) ?
    C7 N1 C9 N2 . . . . -0.7(4) ?
    C7 N1 C9 C13 . . . . 178.7(5) ?
    C8 N2 C9 N1 . . . . 0.3(5) ?
    C10 N2 C9 N1 . . . . -178.8(4) ?
    C8 N2 C9 C13 . . . . -179.2(4) ?
    C10 N2 C9 C13 . . . . 1.7(6) ?
    C12 C13 C9 N1 . . . . 179.3(5) ?
    C12 C13 C9 N2 . . . . -1.4(7) ?
    C12 C11 C10 N2 . . . . 0.8(6) ?
    Br2 C11 C10 N2 . . . . 179.2(3) ?
    C8 N2 C10 C11 . . . . 179.8(4) ?
    C9 N2 C10 C11 . . . . -1.4(6) ?
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
    C5 H5 N1 . 0.93 2.47 2.827(5) 103
    C3 H3 Cg3 7_545 0.93 2.91 3.56700(10)
                                        129
_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     0.429
_shelx_estimated_absorpt_T_max     0.450
