#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229985.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_2229985
loop_
_publ_author_name
'Ouzidan, Younes'
'Jasinski, Jerry P.'
'Butcher, Raymond J.'
'Golen, James A.'
'Essassi, El Mokhtar'
'El Ammari, Lahcen'
_publ_section_title
;
 3-[2-(6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)ethyl]-1,3-oxazolidin-2-one
;
_journal_coeditor_code           GK2362
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1095
_journal_paper_doi               10.1107/S1600536811012669
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H15 Br N4 O2'
_chemical_formula_moiety         'C17 H15 Br N4 O2'
_chemical_formula_sum            'C17 H15 Br N4 O2'
_chemical_formula_weight         387.24
_chemical_name_systematic
;
3-[2-(6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-
3-yl)ethyl]-1,3-oxazolidin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.685(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3553(6)
_cell_length_b                   11.5915(5)
_cell_length_c                   12.2542(8)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      32.25
_cell_measurement_theta_min      3.511
_cell_volume                     1594.46(15)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction XcaliburE Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7850
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_T_max  0.652
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.349
_refine_ls_extinction_coef       0.0047(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0368
_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)+(0.0373P)²+0.4211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                2839
_reflns_number_total             3791
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2362.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229985
_cod_database_fobs_code          2229985
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.83535(2) 0.94591(2) 0.34797(3) 0.05968(13) Uani d . 1 . .
O O1 0.28122(17) 0.80153(15) 0.18265(18) 0.0643(6) Uani d . 1 . .
O O2 0.09323(15) 0.76454(14) 0.20646(16) 0.0521(5) Uani d . 1 . .
N N1 0.61867(17) 0.66117(16) 0.33964(18) 0.0444(5) Uani d . 1 . .
N N2 0.42350(16) 0.82558(14) 0.48010(15) 0.0331(4) Uani d . 1 . .
N N3 0.43353(16) 0.64555(14) 0.41210(15) 0.0341(4) Uani d . 1 . .
N N4 0.22330(16) 0.62233(15) 0.23253(16) 0.0380(4) Uani d . 1 . .
C C1 0.53419(19) 0.70349(17) 0.39157(18) 0.0336(5) Uani d . 1 . .
C C2 0.7057(2) 0.7361(2) 0.3310(2) 0.0476(6) Uani d . 1 . .
H H2A 0.7694 0.7119 0.2943 0.057 Uiso calc R 1 . .
C C3 0.7086(2) 0.84809(19) 0.3727(2) 0.0386(5) Uani d . 1 . .
C C4 0.61915(19) 0.89053(18) 0.42593(18) 0.0347(5) Uani d . 1 . .
H H4A 0.6204 0.9668 0.4544 0.042 Uiso calc R 1 . .
C C5 0.52729(19) 0.81425(17) 0.43494(18) 0.0313(5) Uani d . 1 . .
C C6 0.37023(19) 0.72409(17) 0.46453(17) 0.0314(5) Uani d . 1 . .
C C7 0.3943(2) 0.53819(17) 0.3543(2) 0.0397(5) Uani d . 1 . .
H H7A 0.3378 0.4977 0.3952 0.048 Uiso calc R 1 . .
H H7B 0.4640 0.4872 0.3526 0.048 Uiso calc R 1 . .
C C8 0.3343(2) 0.56137(19) 0.2369(2) 0.0427(6) Uani d . 1 . .
H H8A 0.3888 0.6072 0.1981 0.051 Uiso calc R 1 . .
H H8B 0.3195 0.4870 0.1975 0.051 Uiso calc R 1 . .
C C9 0.2077(2) 0.7339(2) 0.2053(2) 0.0422(6) Uani d . 1 . .
C C10 0.0290(2) 0.6685(2) 0.2428(2) 0.0473(6) Uani d . 1 . .
H H10A -0.0444 0.6533 0.1900 0.057 Uiso calc R 1 . .
H H10B 0.0066 0.6841 0.3164 0.057 Uiso calc R 1 . .
C C11 0.1133(2) 0.5666(2) 0.2479(2) 0.0494(6) Uani d . 1 . .
H H11A 0.1207 0.5270 0.3201 0.059 Uiso calc R 1 . .
H H11B 0.0873 0.5104 0.1882 0.059 Uiso calc R 1 . .
C C12 0.25728(19) 0.69848(18) 0.50368(17) 0.0331(5) Uani d . 1 . .
C C13 0.2346(2) 0.5929(2) 0.5501(2) 0.0491(6) Uani d . 1 . .
H H13A 0.2927 0.5333 0.5559 0.059 Uiso calc R 1 . .
C C14 0.1272(3) 0.5745(2) 0.5880(2) 0.0582(7) Uani d . 1 . .
H H14A 0.1116 0.5019 0.6188 0.070 Uiso calc R 1 . .
C C15 0.0434(2) 0.6598(3) 0.5815(2) 0.0572(7) Uani d . 1 . .
H H15A -0.0304 0.6462 0.6069 0.069 Uiso calc R 1 . .
C C16 0.0661(2) 0.7651(2) 0.5383(2) 0.0511(6) Uani d . 1 . .
H H16A 0.0085 0.8249 0.5350 0.061 Uiso calc R 1 . .
C C17 0.1725(2) 0.7849(2) 0.49934(19) 0.0407(5) Uani d . 1 . .
H H17A 0.1875 0.8581 0.4695 0.049 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 O2 C10 . . 109.50(18) ?
C1 N1 C2 . . 113.39(19) ?
C6 N2 C5 . . 104.87(17) ?
C6 N3 C1 . . 105.55(16) ?
C6 N3 C7 . . 130.08(18) ?
C1 N3 C7 . . 121.58(18) ?
C9 N4 C8 . . 124.4(2) ?
C9 N4 C11 . . 112.3(2) ?
C8 N4 C11 . . 123.08(18) ?
N1 C1 N3 . . 125.98(19) ?
N1 C1 C5 . . 127.6(2) ?
N3 C1 C5 . . 106.39(18) ?
N1 C2 C3 . . 123.7(2) ?
N1 C2 H2A . . 118.1 ?
C3 C2 H2A . . 118.1 ?
C4 C3 C2 . . 121.8(2) ?
C4 C3 Br1 . . 119.65(16) ?
C2 C3 Br1 . . 118.43(17) ?
C3 C4 C5 . . 115.34(19) ?
C3 C4 H4A . . 122.3 ?
C5 C4 H4A . . 122.3 ?
N2 C5 C4 . . 132.04(18) ?
N2 C5 C1 . . 109.89(18) ?
C4 C5 C1 . . 118.07(19) ?
N2 C6 N3 . . 113.29(18) ?
N2 C6 C12 . . 122.43(19) ?
N3 C6 C12 . . 124.24(18) ?
N3 C7 C8 . . 111.52(17) ?
N3 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
N3 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
N4 C8 C7 . . 112.74(19) ?
N4 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
N4 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
O1 C9 N4 . . 127.8(2) ?
O1 C9 O2 . . 122.1(2) ?
N4 C9 O2 . . 110.1(2) ?
O2 C10 C11 . . 105.60(19) ?
O2 C10 H10A . . 110.6 ?
C11 C10 H10A . . 110.6 ?
O2 C10 H10B . . 110.6 ?
C11 C10 H10B . . 110.6 ?
H10A C10 H10B . . 108.8 ?
N4 C11 C10 . . 101.52(18) ?
N4 C11 H11A . . 111.5 ?
C10 C11 H11A . . 111.5 ?
N4 C11 H11B . . 111.5 ?
C10 C11 H11B . . 111.5 ?
H11A C11 H11B . . 109.3 ?
C17 C12 C13 . . 118.8(2) ?
C17 C12 C6 . . 118.60(19) ?
C13 C12 C6 . . 122.5(2) ?
C14 C13 C12 . . 119.9(2) ?
C14 C13 H13A . . 120.0 ?
C12 C13 H13A . . 120.0 ?
C15 C14 C13 . . 120.7(2) ?
C15 C14 H14A . . 119.7 ?
C13 C14 H14A . . 119.7 ?
C14 C15 C16 . . 119.8(2) ?
C14 C15 H15A . . 120.1 ?
C16 C15 H15A . . 120.1 ?
C15 C16 C17 . . 120.4(2) ?
C15 C16 H16A . . 119.8 ?
C17 C16 H16A . . 119.8 ?
C16 C17 C12 . . 120.3(2) ?
C16 C17 H17A . . 119.8 ?
C12 C17 H17A . . 119.8 ?
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 C3 . 1.892(2) ?
O1 C9 . 1.208(3) ?
O2 C9 . 1.349(3) ?
O2 C10 . 1.438(3) ?
N1 C1 . 1.323(3) ?
N1 C2 . 1.332(3) ?
N2 C6 . 1.323(3) ?
N2 C5 . 1.382(3) ?
N3 C6 . 1.378(3) ?
N3 C1 . 1.381(3) ?
N3 C7 . 1.467(3) ?
N4 C9 . 1.340(3) ?
N4 C8 . 1.439(3) ?
N4 C11 . 1.443(3) ?
C1 C5 . 1.396(3) ?
C2 C3 . 1.393(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.378(3) ?
C4 C5 . 1.385(3) ?
C4 H4A . 0.9500 ?
C6 C12 . 1.466(3) ?
C7 C8 . 1.520(4) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C10 C11 . 1.516(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C17 . 1.385(3) ?
C12 C13 . 1.390(3) ?
C13 C14 . 1.385(4) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.366(4) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.370(4) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.383(3) ?
C16 H16A . 0.9500 ?
C17 H17A . 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 H4A N2 3_676 0.95 2.61 3.544(3) 168
C10 H10A N2 4_575 0.99 2.55 3.261(3) 128
C15 H15A O1 4_576 0.95 2.53 3.423(3) 156
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
C2 N1 C1 N3 . . . . 179.8(2) ?
C2 N1 C1 C5 . . . . 0.7(4) ?
C6 N3 C1 N1 . . . . -178.2(2) ?
C7 N3 C1 N1 . . . . -15.3(3) ?
C6 N3 C1 C5 . . . . 1.1(2) ?
C7 N3 C1 C5 . . . . 163.93(19) ?
C1 N1 C2 C3 . . . . 0.3(4) ?
N1 C2 C3 C4 . . . . -0.7(4) ?
N1 C2 C3 Br1 . . . . -177.4(2) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
Br1 C3 C4 C5 . . . . 176.72(16) ?
C6 N2 C5 C4 . . . . 179.9(2) ?
C6 N2 C5 C1 . . . . 0.3(2) ?
C3 C4 C5 N2 . . . . -178.8(2) ?
C3 C4 C5 C1 . . . . 0.8(3) ?
N1 C1 C5 N2 . . . . 178.3(2) ?
N3 C1 C5 N2 . . . . -0.9(2) ?
N1 C1 C5 C4 . . . . -1.3(4) ?
N3 C1 C5 C4 . . . . 179.46(19) ?
C5 N2 C6 N3 . . . . 0.4(2) ?
C5 N2 C6 C12 . . . . 178.28(19) ?
C1 N3 C6 N2 . . . . -1.0(2) ?
C7 N3 C6 N2 . . . . -161.8(2) ?
C1 N3 C6 C12 . . . . -178.78(19) ?
C7 N3 C6 C12 . . . . 20.4(3) ?
C6 N3 C7 C8 . . . . 81.7(3) ?
C1 N3 C7 C8 . . . . -76.4(3) ?
C9 N4 C8 C7 . . . . 106.1(3) ?
C11 N4 C8 C7 . . . . -79.5(3) ?
N3 C7 C8 N4 . . . . -66.7(2) ?
C8 N4 C9 O1 . . . . -1.6(4) ?
C11 N4 C9 O1 . . . . -176.5(3) ?
C8 N4 C9 O2 . . . . 178.6(2) ?
C11 N4 C9 O2 . . . . 3.7(3) ?
C10 O2 C9 O1 . . . . -176.5(2) ?
C10 O2 C9 N4 . . . . 3.3(3) ?
C9 O2 C10 C11 . . . . -8.5(3) ?
C9 N4 C11 C10 . . . . -8.5(3) ?
C8 N4 C11 C10 . . . . 176.5(2) ?
O2 C10 C11 N4 . . . . 9.8(3) ?
N2 C6 C12 C17 . . . . 36.7(3) ?
N3 C6 C12 C17 . . . . -145.7(2) ?
N2 C6 C12 C13 . . . . -139.9(2) ?
N3 C6 C12 C13 . . . . 37.7(3) ?
C17 C12 C13 C14 . . . . 1.9(4) ?
C6 C12 C13 C14 . . . . 178.5(2) ?
C12 C13 C14 C15 . . . . -0.8(4) ?
C13 C14 C15 C16 . . . . -0.7(5) ?
C14 C15 C16 C17 . . . . 1.1(4) ?
C15 C16 C17 C12 . . . . 0.0(4) ?
C13 C12 C17 C16 . . . . -1.5(4) ?
C6 C12 C17 C16 . . . . -178.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656633
