#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/68/2226815.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_2226815
loop_
_publ_author_name
'Dahmani, Siham'
'Rodi, Youssef Kandri'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 6-Bromo-1,3-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one
;
_journal_coeditor_code           CI5119
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1904
_journal_paper_doi               10.1107/S1600536810025134
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H8 Br N3 O'
_chemical_formula_moiety         'C8 H8 Br N3 O'
_chemical_formula_sum            'C8 H8 Br N3 O'
_chemical_formula_weight         242.08
_chemical_name_systematic
;
6-Bromo-1,3-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 95.3980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.7981(4)
_cell_length_b                   3.99290(10)
_cell_length_c                   20.6636(3)
_cell_measurement_reflns_used    6375
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.6
_cell_volume                     1790.53(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEXII area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21586
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.552
_exptl_absorpt_correction_T_max  0.5484
_exptl_absorpt_correction_T_min  0.3957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.1144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                3539
_reflns_number_total             5229
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5119.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226815
_cod_database_fobs_code          2226815
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.407800(11) 0.91753(7) 0.468246(11) 0.05023(9) Uani d . 1 . .
N N1 0.44555(8) 0.5071(5) 0.65032(9) 0.0416(4) Uani d . 1 . .
N N2 0.37942(8) 0.4903(5) 0.73723(8) 0.0400(4) Uani d . 1 . .
N N3 0.29799(8) 0.7480(5) 0.68786(8) 0.0387(4) Uani d . 1 . .
N N4 0.05385(8) 0.5642(5) 0.92033(9) 0.0400(4) Uani d . 1 . .
N N5 0.12070(8) 0.8692(5) 0.99889(8) 0.0391(4) Uani d . 1 . .
N N6 0.19961(8) 0.9449(5) 0.94033(8) 0.0373(4) Uani d . 1 . .
O O1 0.29345(8) 0.5668(5) 0.79455(8) 0.0568(5) Uani d . 1 . .
O O2 0.20597(8) 1.1650(5) 1.04514(8) 0.0576(5) Uani d . 1 . .
C C1 0.44708(10) 0.6147(6) 0.58839(11) 0.0421(5) Uani d . 1 . .
H H1 0.4826 0.5767 0.5678 0.050 Uiso calc R 1 . .
C C2 0.39881(10) 0.7769(6) 0.55465(10) 0.0374(5) Uani d . 1 . .
C C3 0.34349(10) 0.8436(5) 0.58128(10) 0.0356(5) Uani d . 1 . .
H H3 0.3105 0.9528 0.5585 0.043 Uiso calc R 1 . .
C C4 0.34205(9) 0.7335(5) 0.64419(10) 0.0339(4) Uani d . 1 . .
C C5 0.39361(9) 0.5704(5) 0.67562(10) 0.0345(5) Uani d . 1 . .
C C6 0.42023(12) 0.3314(7) 0.78847(13) 0.0546(7) Uani d . 1 . .
H H6A 0.3960 0.2231 0.8188 0.082 Uiso calc R 1 . .
H H6B 0.4460 0.4983 0.8107 0.082 Uiso calc R 1 . .
H H6C 0.4455 0.1684 0.7696 0.082 Uiso calc R 1 . .
C C7 0.32072(10) 0.5976(6) 0.74587(11) 0.0411(5) Uani d . 1 . .
C C8 0.23694(10) 0.8923(7) 0.67783(13) 0.0503(6) Uani d . 1 . .
H H8A 0.2289 1.0214 0.7153 0.075 Uiso calc R 1 . .
H H8B 0.2070 0.7164 0.6713 0.075 Uiso calc R 1 . .
H H8C 0.2344 1.0348 0.6402 0.075 Uiso calc R 1 . .
C C9 0.05044(10) 0.4500(6) 0.85870(11) 0.0415(5) Uani d . 1 . .
H H9 0.0149 0.3385 0.8423 0.050 Uiso calc R 1 . .
C C10 0.09723(10) 0.4905(5) 0.81873(10) 0.0356(5) Uani d . 1 . .
C C11 0.15197(9) 0.6529(5) 0.83943(10) 0.0350(5) Uani d . 1 . .
H H11 0.1839 0.6795 0.8130 0.042 Uiso calc R 1 . .
C C12 0.15516(9) 0.7711(5) 0.90210(9) 0.0311(4) Uani d . 1 . .
C C13 0.10513(9) 0.7226(5) 0.93943(10) 0.0337(4) Uani d . 1 . .
C C14 0.08264(13) 0.8834(8) 1.05313(13) 0.0621(8) Uani d . 1 . .
H H14A 0.1083 0.8604 1.0933 0.093 Uiso calc R 1 . .
H H14B 0.0530 0.7048 1.0492 0.093 Uiso calc R 1 . .
H H14C 0.0615 1.0945 1.0526 0.093 Uiso calc R 1 . .
C C15 0.17830(10) 1.0112(6) 0.99985(11) 0.0408(5) Uani d . 1 . .
C C16 0.25863(10) 1.0616(6) 0.92138(12) 0.0474(6) Uani d . 1 . .
H H16A 0.2842 1.1318 0.9593 0.071 Uiso calc R 1 . .
H H16B 0.2520 1.2468 0.8919 0.071 Uiso calc R 1 . .
H H16C 0.2786 0.8829 0.9004 0.071 Uiso calc R 1 . .
Br Br2 0.086179(12) 0.32023(7) 0.732957(11) 0.05183(9) Uani d . 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
C5 N1 C1 . . 114.43(18) ?
C5 N2 C7 . . 109.90(17) ?
C5 N2 C6 . . 126.63(19) ?
C7 N2 C6 . . 123.40(19) ?
C4 N3 C7 . . 109.41(18) ?
C4 N3 C8 . . 127.62(19) ?
C7 N3 C8 . . 122.96(19) ?
C13 N4 C9 . . 114.63(18) ?
C13 N5 C15 . . 109.67(18) ?
C13 N5 C14 . . 126.4(2) ?
C15 N5 C14 . . 123.9(2) ?
C12 N6 C15 . . 109.26(17) ?
C12 N6 C16 . . 126.73(18) ?
C15 N6 C16 . . 123.92(19) ?
N1 C1 C2 . . 123.1(2) ?
N1 C1 H1 . . 118.5 ?
C2 C1 H1 . . 118.5 ?
C1 C2 C3 . . 122.7(2) ?
C1 C2 Br1 . . 118.44(16) ?
C3 C2 Br1 . . 118.88(16) ?
C4 C3 C2 . . 114.1(2) ?
C4 C3 H3 . . 122.9 ?
C2 C3 H3 . . 122.9 ?
C3 C4 N3 . . 133.2(2) ?
C3 C4 C5 . . 119.79(19) ?
N3 C4 C5 . . 107.04(18) ?
N1 C5 N2 . . 126.9(2) ?
N1 C5 C4 . . 125.9(2) ?
N2 C5 C4 . . 107.22(18) ?
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 ?
O1 C7 N2 . . 127.3(2) ?
O1 C7 N3 . . 126.3(2) ?
N2 C7 N3 . . 106.43(18) ?
N3 C8 H8A . . 109.5 ?
N3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N4 C9 C10 . . 123.2(2) ?
N4 C9 H9 . . 118.4 ?
C10 C9 H9 . . 118.4 ?
C9 C10 C11 . . 122.1(2) ?
C9 C10 Br2 . . 118.81(16) ?
C11 C10 Br2 . . 119.06(16) ?
C12 C11 C10 . . 114.59(19) ?
C12 C11 H11 . . 122.7 ?
C10 C11 H11 . . 122.7 ?
N6 C12 C11 . . 133.1(2) ?
N6 C12 C13 . . 107.11(17) ?
C11 C12 C13 . . 119.8(2) ?
N4 C13 N5 . . 127.28(19) ?
N4 C13 C12 . . 125.70(19) ?
N5 C13 C12 . . 107.02(18) ?
N5 C14 H14A . . 109.5 ?
N5 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N5 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O2 C15 N6 . . 126.3(2) ?
O2 C15 N5 . . 126.8(2) ?
N6 C15 N5 . . 106.92(18) ?
N6 C16 H16A . . 109.5 ?
N6 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N6 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 C2 . 1.899(2) ?
N1 C5 . 1.316(3) ?
N1 C1 . 1.353(3) ?
N2 C5 . 1.376(3) ?
N2 C7 . 1.377(3) ?
N2 C6 . 1.462(3) ?
N3 C4 . 1.380(3) ?
N3 C7 . 1.390(3) ?
N3 C8 . 1.447(3) ?
N4 C13 . 1.313(3) ?
N4 C9 . 1.348(3) ?
N5 C13 . 1.374(3) ?
N5 C15 . 1.376(3) ?
N5 C14 . 1.457(3) ?
N6 C12 . 1.379(3) ?
N6 C15 . 1.381(3) ?
N6 C16 . 1.456(3) ?
O1 C7 . 1.222(3) ?
O2 C15 . 1.229(3) ?
C1 C2 . 1.369(3) ?
C1 H1 . 0.93 ?
C2 C3 . 1.397(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.404(3) ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C10 . 1.381(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.390(3) ?
C10 Br2 . 1.893(2) ?
C11 C12 . 1.374(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.407(3) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
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
C8 H8C O2 4_585 0.96 2.33 3.279(3) 167
C11 H11 O1 . 0.93 2.49 3.321(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 0.2(3) ?
N1 C1 C2 C3 . . . . -0.4(4) ?
N1 C1 C2 Br1 . . . . 179.39(17) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
Br1 C2 C3 C4 . . . . -179.52(15) ?
C2 C3 C4 N3 . . . . 179.6(2) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C7 N3 C4 C3 . . . . -179.7(2) ?
C8 N3 C4 C3 . . . . 0.5(4) ?
C7 N3 C4 C5 . . . . -0.1(2) ?
C8 N3 C4 C5 . . . . -179.9(2) ?
C1 N1 C5 N2 . . . . -179.9(2) ?
C1 N1 C5 C4 . . . . 0.1(3) ?
C7 N2 C5 N1 . . . . 180.0(2) ?
C6 N2 C5 N1 . . . . 3.0(4) ?
C7 N2 C5 C4 . . . . -0.1(2) ?
C6 N2 C5 C4 . . . . -177.1(2) ?
C3 C4 C5 N1 . . . . -0.3(3) ?
N3 C4 C5 N1 . . . . -180.0(2) ?
C3 C4 C5 N2 . . . . 179.80(19) ?
N3 C4 C5 N2 . . . . 0.1(2) ?
C5 N2 C7 O1 . . . . 179.8(2) ?
C6 N2 C7 O1 . . . . -3.1(4) ?
C5 N2 C7 N3 . . . . 0.1(3) ?
C6 N2 C7 N3 . . . . 177.2(2) ?
C4 N3 C7 O1 . . . . -179.7(2) ?
C8 N3 C7 O1 . . . . 0.1(4) ?
C4 N3 C7 N2 . . . . 0.0(3) ?
C8 N3 C7 N2 . . . . 179.8(2) ?
C13 N4 C9 C10 . . . . 0.9(3) ?
N4 C9 C10 C11 . . . . 0.2(3) ?
N4 C9 C10 Br2 . . . . -179.59(17) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
Br2 C10 C11 C12 . . . . 179.19(15) ?
C15 N6 C12 C11 . . . . 178.1(2) ?
C16 N6 C12 C11 . . . . 1.5(4) ?
C15 N6 C12 C13 . . . . -1.1(2) ?
C16 N6 C12 C13 . . . . -177.7(2) ?
C10 C11 C12 N6 . . . . -179.2(2) ?
C10 C11 C12 C13 . . . . -0.1(3) ?
C9 N4 C13 N5 . . . . 178.9(2) ?
C9 N4 C13 C12 . . . . -1.7(3) ?
C15 N5 C13 N4 . . . . -179.7(2) ?
C14 N5 C13 N4 . . . . -1.1(4) ?
C15 N5 C13 C12 . . . . 0.8(2) ?
C14 N5 C13 C12 . . . . 179.4(2) ?
N6 C12 C13 N4 . . . . -179.3(2) ?
C11 C12 C13 N4 . . . . 1.4(3) ?
N6 C12 C13 N5 . . . . 0.2(2) ?
C11 C12 C13 N5 . . . . -179.13(19) ?
C12 N6 C15 O2 . . . . -179.2(2) ?
C16 N6 C15 O2 . . . . -2.4(4) ?
C12 N6 C15 N5 . . . . 1.5(2) ?
C16 N6 C15 N5 . . . . 178.30(19) ?
C13 N5 C15 O2 . . . . 179.3(2) ?
C14 N5 C15 O2 . . . . 0.6(4) ?
C13 N5 C15 N6 . . . . -1.4(2) ?
C14 N5 C15 N6 . . . . 179.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079267
