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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228262.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228262
loop_
_publ_author_name
'Wang, Haixia'
_publ_section_title
;
 2-(5,6-Dibromo-7-methyl-3H-imidazo[4,5-b]pyridin-2-yl)phenol
;
_journal_coeditor_code           CV2784
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3132
_journal_paper_doi               10.1107/S1600536810045277
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 Br2 N3 O'
_chemical_formula_moiety         'C13 H9 Br2 N3 O'
_chemical_formula_sum            'C13 H9 Br2 N3 O'
_chemical_formula_weight         383.05
_chemical_name_systematic
;
2-(5,6-Dibromo-7-methyl-3H-imidazo[4,5-b]pyridin-2-yl)phenol
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.181(5)
_cell_length_b                   8.494(3)
_cell_length_c                   22.692(8)
_cell_measurement_reflns_used    1452
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.631
_cell_measurement_theta_min      2.871
_cell_volume                     2540.6(16)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11656
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    6.376
_exptl_absorpt_correction_T_max  0.3099
_exptl_absorpt_correction_T_min  0.2426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            orange--yellow
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.880
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0692P)²+6.5580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                1706
_reflns_number_total             2234
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2784.cif
_cod_data_source_block           I
_cod_original_cell_volume        2540.5(16)
_cod_database_code               2228262
_cod_database_fobs_code          2228262
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.27968(6) 1.22305(9) 0.48970(3) 0.0618(3) Uani d . 1 . .
Br Br2 0.51701(6) 1.19032(9) 0.54180(3) 0.0669(3) Uani d . 1 . .
O O1 0.0310(3) 0.7707(6) 0.73898(19) 0.0541(12) Uani d . 1 . .
H H1 0.0614 0.8111 0.7113 0.081 Uiso d R 1 . .
N N1 0.3413(3) 0.8522(5) 0.7102(2) 0.0380(10) Uani d . 1 . .
H H1A 0.4011 0.8215 0.7306 0.046 Uiso d R 1 . .
N N2 0.1806(3) 0.8887(5) 0.68102(19) 0.0365(10) Uani d . 1 . .
N N3 0.4280(4) 1.0090(7) 0.6313(2) 0.0615(15) Uani d . 1 . .
C C1 0.3468(4) 0.9445(6) 0.6601(2) 0.0348(12) Uani d . 1 . .
C C2 0.2452(4) 0.9659(6) 0.6416(2) 0.0350(12) Uani d . 1 . .
C C3 0.2226(4) 1.0517(7) 0.5909(2) 0.0432(13) Uani d . 1 . .
C C4 0.3060(4) 1.1146(7) 0.5612(2) 0.0414(13) Uani d . 1 . .
C C5 0.4049(4) 1.0950(6) 0.5811(2) 0.0400(13) Uani d . 1 . .
C C6 0.1127(5) 1.0806(9) 0.5643(3) 0.0680(19) Uani d . 1 . .
H H6A 0.0923 1.1873 0.5717 0.102 Uiso calc R 1 . .
H H6B 0.0653 1.0098 0.5825 0.102 Uiso calc R 1 . .
H H6C 0.1140 1.0621 0.5226 0.102 Uiso calc R 1 . .
C C7 0.2410(4) 0.8221(6) 0.7213(2) 0.0357(12) Uani d . 1 . .
C C8 0.2041(4) 0.7275(6) 0.7696(2) 0.0354(12) Uani d . 1 . .
C C9 0.0988(5) 0.7064(7) 0.7768(3) 0.0431(13) Uani d . 1 . .
C C10 0.0636(5) 0.6169(8) 0.8237(3) 0.0578(17) Uani d . 1 . .
H H10 -0.0057 0.6022 0.8288 0.069 Uiso calc R 1 . .
C C11 0.1315(5) 0.5488(8) 0.8632(3) 0.0604(18) Uani d . 1 . .
H H11 0.1074 0.4895 0.8947 0.072 Uiso calc R 1 . .
C C12 0.2329(5) 0.5690(8) 0.8558(3) 0.0536(16) Uani d . 1 . .
H H12 0.2779 0.5226 0.8821 0.064 Uiso calc R 1 . .
C C13 0.2693(4) 0.6560(7) 0.8104(3) 0.0453(14) Uani d . 1 . .
H H13 0.3390 0.6686 0.8063 0.054 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
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
C9 O1 H1 . . 109.5 ?
C7 N1 C1 . . 107.9(4) ?
C7 N1 H1A . . 131.3 ?
C1 N1 H1A . . 120.8 ?
C7 N2 C2 . . 105.9(4) ?
C1 N3 C5 . . 115.6(5) ?
N3 C1 N1 . . 131.4(5) ?
N3 C1 C2 . . 123.1(5) ?
N1 C1 C2 . . 105.6(4) ?
C3 C2 N2 . . 130.1(5) ?
C3 C2 C1 . . 121.0(5) ?
N2 C2 C1 . . 109.0(5) ?
C2 C3 C4 . . 115.5(5) ?
C2 C3 C6 . . 126.1(5) ?
C4 C3 C6 . . 118.4(5) ?
C5 C4 C3 . . 122.4(5) ?
C5 C4 Br1 . . 120.5(4) ?
C3 C4 Br1 . . 117.1(4) ?
N3 C5 C4 . . 122.5(5) ?
N3 C5 Br2 . . 115.9(4) ?
C4 C5 Br2 . . 121.6(4) ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N2 C7 N1 . . 111.7(5) ?
N2 C7 C8 . . 123.6(5) ?
N1 C7 C8 . . 124.7(5) ?
C13 C8 C9 . . 118.1(5) ?
C13 C8 C7 . . 122.4(5) ?
C9 C8 C7 . . 119.5(5) ?
O1 C9 C10 . . 119.1(6) ?
O1 C9 C8 . . 121.6(5) ?
C10 C9 C8 . . 119.3(6) ?
C9 C10 C11 . . 120.4(6) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C12 C11 C10 . . 120.0(6) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.8(6) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C8 . . 121.5(5) ?
C12 C13 H13 . . 119.3 ?
C8 C13 H13 . . 119.3 ?
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
Br1 C4 . 1.897(6) ?
Br2 C5 . 1.907(5) ?
O1 C9 . 1.354(7) ?
O1 H1 . 0.8200 ?
N1 C7 . 1.369(7) ?
N1 C1 . 1.382(7) ?
N1 H1A . 0.9504 ?
N2 C7 . 1.338(7) ?
N2 C2 . 1.398(7) ?
N3 C1 . 1.370(7) ?
N3 C5 . 1.387(8) ?
C1 C2 . 1.415(7) ?
C2 C3 . 1.394(8) ?
C3 C4 . 1.396(8) ?
C3 C6 . 1.589(9) ?
C4 C5 . 1.389(8) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C8 . 1.442(8) ?
C8 C13 . 1.402(8) ?
C8 C9 . 1.408(8) ?
C9 C10 . 1.388(8) ?
C10 C11 . 1.392(9) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.358(9) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.355(8) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cg1 Cg2 3.760(3) . 8_665 n
Cg1 Cg3 3.723(3) . 8_655 n
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
N1 H1A O1 6_657 0.95 1.90 2.839(6) 171.4
O1 H1 N2 . 0.82 1.84 2.573(6) 148.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656339
2 PubChem 136614025
