#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224885.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_2224885
loop_
_publ_author_name
'Bel-Ghacham, H.'
'Kandri Rodi, Y.'
'Saffon, Natalie'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-imidazo[4,5-b]pyridin-2(3H)-one
_journal_coeditor_code           BT5180
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o456
_journal_paper_doi               10.1107/S1600536810002679
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H11 Br N4 O3'
_chemical_formula_moiety         'C11 H11 Br N4 O3'
_chemical_formula_sum            'C11 H11 Br N4 O3'
_chemical_formula_weight         327.15
_chemical_name_systematic
;
6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-
imidazo[4,5-b]pyridin-2(3H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 110.343(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.0174(11)
_cell_length_b                   6.0141(2)
_cell_length_c                   16.6121(6)
_cell_measurement_reflns_used    1559
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      2.6
_cell_volume                     2530.87(16)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII diffractometer'
_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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9174
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.259
_exptl_absorpt_correction_T_max  0.8540
_exptl_absorpt_correction_T_min  0.3556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0380
_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)+(0.0269P)²+1.8498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                1633
_reflns_number_total             2224
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5180.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224885
_cod_database_fobs_code          2224885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.030317(17) 1.14052(7) 0.39869(3) 0.03436(15) Uani d . 1 . .
O O1 0.07133(11) 0.4365(4) 0.17338(18) 0.0398(8) Uani d . 1 . .
O O2 0.14847(12) 0.2803(5) 0.25167(18) 0.0447(8) Uani d . 1 . .
O O3 0.26482(10) 0.4281(4) 0.42343(15) 0.0266(6) Uani d . 1 . .
N N1 0.14287(12) 0.6468(5) 0.21101(17) 0.0236(7) Uani d . 1 . .
N N2 0.20224(12) 0.7116(5) 0.38942(18) 0.0197(7) Uani d . 1 . .
N N3 0.19871(12) 0.4599(5) 0.48386(18) 0.0225(7) Uani d D 1 . .
H H3 0.2052(13) 0.339(3) 0.5132(18) 0.022(10) Uiso d D 1 . .
N N4 0.12421(12) 0.6066(5) 0.51587(18) 0.0242(7) Uani d . 1 . .
C C1 0.12398(18) 0.4418(7) 0.2151(2) 0.0307(10) Uani d . 1 . .
C C2 0.05337(18) 0.6589(7) 0.1444(3) 0.0565(14) Uani d . 1 . .
H H2A 0.0354 0.7266 0.1812 0.068 Uiso calc R 1 . .
H H2B 0.0286 0.6568 0.0843 0.068 Uiso calc R 1 . .
C C3 0.10292(17) 0.7865(6) 0.1514(3) 0.0366(11) Uani d . 1 . .
H H3A 0.1079 0.7975 0.0953 0.044 Uiso calc R 1 . .
H H3B 0.1026 0.9376 0.1749 0.044 Uiso calc R 1 . .
C C4 0.19838(15) 0.6905(6) 0.2399(2) 0.0261(9) Uani d . 1 . .
H H4A 0.2065 0.7762 0.1951 0.031 Uiso calc R 1 . .
H H4B 0.2176 0.5474 0.2474 0.031 Uiso calc R 1 . .
C C5 0.21827(15) 0.8193(6) 0.3239(2) 0.0221(9) Uani d . 1 . .
H H5A 0.2573 0.8290 0.3439 0.027 Uiso calc R 1 . .
H H5B 0.2040 0.9725 0.3143 0.027 Uiso calc R 1 . .
C C6 0.22613(15) 0.5212(6) 0.4313(2) 0.0220(9) Uani d . 1 . .
C C7 0.15790(14) 0.6070(6) 0.4745(2) 0.0198(8) Uani d . 1 . .
C C8 0.08786(15) 0.7701(6) 0.4925(2) 0.0268(9) Uani d . 1 . .
H H8 0.0624 0.7777 0.5201 0.032 Uiso calc R 1 . .
C C9 0.08554(15) 0.9282(6) 0.4302(2) 0.0227(9) Uani d . 1 . .
C C10 0.12232(15) 0.9304(6) 0.3887(2) 0.0220(9) Uani d . 1 . .
H H10 0.1218 1.0386 0.3468 0.026 Uiso calc R 1 . .
C C11 0.15928(14) 0.7649(6) 0.4130(2) 0.0183(8) 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
C1 O1 C2 . . 108.7(3) ?
C1 N1 C4 . . 121.6(3) ?
C1 N1 C3 . . 111.1(3) ?
C4 N1 C3 . . 124.5(3) ?
C6 N2 C11 . . 109.9(3) ?
C6 N2 C5 . . 122.6(3) ?
C11 N2 C5 . . 127.2(3) ?
C6 N3 C7 . . 110.0(3) ?
C6 N3 H3 . . 123(2) ?
C7 N3 H3 . . 127(2) ?
C7 N4 C8 . . 114.5(3) ?
O2 C1 N1 . . 127.5(4) ?
O2 C1 O1 . . 122.2(4) ?
N1 C1 O1 . . 110.3(3) ?
O1 C2 C3 . . 104.9(3) ?
O1 C2 H2A . . 110.8 ?
C3 C2 H2A . . 110.8 ?
O1 C2 H2B . . 110.8 ?
C3 C2 H2B . . 110.8 ?
H2A C2 H2B . . 108.8 ?
N1 C3 C2 . . 100.8(3) ?
N1 C3 H3A . . 111.6 ?
C2 C3 H3A . . 111.6 ?
N1 C3 H3B . . 111.6 ?
C2 C3 H3B . . 111.6 ?
H3A C3 H3B . . 109.4 ?
N1 C4 C5 . . 113.3(3) ?
N1 C4 H4A . . 108.9 ?
C5 C4 H4A . . 108.9 ?
N1 C4 H4B . . 108.9 ?
C5 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.7 ?
N2 C5 C4 . . 110.9(3) ?
N2 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
N2 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.0 ?
O3 C6 N3 . . 127.5(3) ?
O3 C6 N2 . . 126.1(3) ?
N3 C6 N2 . . 106.4(3) ?
N4 C7 N3 . . 127.6(3) ?
N4 C7 C11 . . 125.3(3) ?
N3 C7 C11 . . 107.1(3) ?
N4 C8 C9 . . 123.6(3) ?
N4 C8 H8 . . 118.2 ?
C9 C8 H8 . . 118.2 ?
C8 C9 C10 . . 121.3(3) ?
C8 C9 Br1 . . 119.6(3) ?
C10 C9 Br1 . . 119.1(3) ?
C11 C10 C9 . . 114.9(3) ?
C11 C10 H10 . . 122.6 ?
C9 C10 H10 . . 122.6 ?
C10 C11 N2 . . 133.1(3) ?
C10 C11 C7 . . 120.3(3) ?
N2 C11 C7 . . 106.6(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 C9 . 1.894(4) ?
O1 C1 . 1.349(5) ?
O1 C2 . 1.447(5) ?
O2 C1 . 1.213(4) ?
O3 C6 . 1.232(4) ?
N1 C1 . 1.345(5) ?
N1 C4 . 1.431(4) ?
N1 C3 . 1.452(5) ?
N2 C6 . 1.378(4) ?
N2 C11 . 1.385(4) ?
N2 C5 . 1.457(4) ?
N3 C6 . 1.377(4) ?
N3 C7 . 1.380(4) ?
N3 H3 . 0.859(10) ?
N4 C7 . 1.318(4) ?
N4 C8 . 1.348(4) ?
C2 C3 . 1.512(6) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.521(5) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C7 C11 . 1.405(5) ?
C8 C9 . 1.390(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.393(5) ?
C10 C11 . 1.368(5) ?
C10 H10 . 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
_geom_hbond_publ_flag
N3 H3 O3 7_556 0.860(10) 1.940(10) 2.781(4) 167(3) yes
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
C4 N1 C1 O2 . . . . 10.3(6) ?
C3 N1 C1 O2 . . . . 171.9(4) ?
C4 N1 C1 O1 . . . . -171.3(3) ?
C3 N1 C1 O1 . . . . -9.7(4) ?
C2 O1 C1 O2 . . . . 174.3(4) ?
C2 O1 C1 N1 . . . . -4.2(4) ?
C1 O1 C2 C3 . . . . 15.5(5) ?
C1 N1 C3 C2 . . . . 18.3(4) ?
C4 N1 C3 C2 . . . . 179.3(3) ?
O1 C2 C3 N1 . . . . -19.6(4) ?
C1 N1 C4 C5 . . . . -107.3(4) ?
C3 N1 C4 C5 . . . . 93.6(4) ?
C6 N2 C5 C4 . . . . 75.4(4) ?
C11 N2 C5 C4 . . . . -97.5(4) ?
N1 C4 C5 N2 . . . . 52.5(4) ?
C7 N3 C6 O3 . . . . 179.9(4) ?
C7 N3 C6 N2 . . . . 0.8(4) ?
C11 N2 C6 O3 . . . . 178.8(4) ?
C5 N2 C6 O3 . . . . 4.8(6) ?
C11 N2 C6 N3 . . . . -2.1(4) ?
C5 N2 C6 N3 . . . . -176.1(3) ?
C8 N4 C7 N3 . . . . -179.2(3) ?
C8 N4 C7 C11 . . . . 2.5(5) ?
C6 N3 C7 N4 . . . . -177.8(3) ?
C6 N3 C7 C11 . . . . 0.8(4) ?
C7 N4 C8 C9 . . . . -0.2(5) ?
N4 C8 C9 C10 . . . . -1.6(6) ?
N4 C8 C9 Br1 . . . . 176.7(3) ?
C8 C9 C10 C11 . . . . 1.2(5) ?
Br1 C9 C10 C11 . . . . -177.2(3) ?
C9 C10 C11 N2 . . . . -178.5(4) ?
C9 C10 C11 C7 . . . . 0.9(5) ?
C6 N2 C11 C10 . . . . -178.0(4) ?
C5 N2 C11 C10 . . . . -4.3(6) ?
C6 N2 C11 C7 . . . . 2.6(4) ?
C5 N2 C11 C7 . . . . 176.2(3) ?
N4 C7 C11 C10 . . . . -2.9(6) ?
N3 C7 C11 C10 . . . . 178.5(3) ?
N4 C7 C11 N2 . . . . 176.6(3) ?
N3 C7 C11 N2 . . . . -2.0(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744358
