#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229039.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_2229039
loop_
_publ_author_name
'Ouzidan, Younes'
'Kandri Rodi, Youssef'
'Fronczek, Frank R.'
'Venkatraman, Ramaiyer'
'El Ammari, Lahcen'
'Essassi, El Mokhtar'
_publ_section_title
;
 1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           FJ2373
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o362
_journal_page_last               o363
_journal_paper_doi               10.1107/S1600536810052141
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H20 N4 O5'
_chemical_formula_moiety         'C17 H20 N4 O5'
_chemical_formula_sum            'C17 H20 N4 O5'
_chemical_formula_weight         360.37
_chemical_name_systematic
;
1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol-
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
_cell_angle_beta                 103.258(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5331(10)
_cell_length_b                   10.9647(10)
_cell_length_c                   14.5541(14)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      4.0
_cell_volume                     1636.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15549
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.2
_diffrn_reflns_theta_min         4.3
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0315P)²+0.8105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                2842
_reflns_number_total             2914
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2373.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229039
_cod_database_fobs_code          2229039
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
O O1 0.51156(8) 0.90454(8) 0.65034(6) 0.01864(19) Uani d . 1 . .
O O2 0.81349(8) 0.63845(8) 0.39970(6) 0.0221(2) Uani d . 1 . .
O O3 0.61653(8) 0.68768(8) 0.42496(6) 0.0209(2) Uani d . 1 . .
O O4 0.22108(8) 0.77982(8) 0.47938(6) 0.01792(19) Uani d . 1 . .
O O5 0.18927(8) 0.77876(8) 0.62760(6) 0.0217(2) Uani d . 1 . .
N N1 0.71846(9) 0.83091(9) 0.64775(7) 0.0145(2) Uani d . 1 . .
N N2 0.58627(9) 0.71116(9) 0.70549(7) 0.0143(2) Uani d . 1 . .
N N3 0.79091(9) 0.81926(9) 0.46197(7) 0.0149(2) Uani d . 1 . .
N N4 0.33456(9) 0.64839(9) 0.58183(7) 0.0158(2) Uani d . 1 . .
C C1 0.59511(11) 0.82469(11) 0.66601(8) 0.0143(2) Uani d . 1 . .
C C2 0.78498(11) 0.72200(10) 0.67384(8) 0.0142(2) Uani d . 1 . .
C C3 0.70112(11) 0.64616(11) 0.71027(7) 0.0137(2) Uani d . 1 . .
C C4 0.73829(11) 0.52998(11) 0.74338(8) 0.0157(2) Uani d . 1 . .
H H4 0.6828 0.4800 0.7679 0.019 Uiso calc R 1 . .
C C5 0.86290(11) 0.49150(11) 0.73819(8) 0.0174(3) Uani d . 1 . .
H H5 0.8907 0.4137 0.7591 0.021 Uiso calc R 1 . .
C C6 0.94645(11) 0.56687(11) 0.70237(8) 0.0176(3) Uani d . 1 . .
H H6 1.0288 0.5384 0.7000 0.021 Uiso calc R 1 . .
C C7 0.90915(11) 0.68422(11) 0.66999(8) 0.0162(2) Uani d . 1 . .
H H7 0.9653 0.7350 0.6468 0.019 Uiso calc R 1 . .
C C8 0.76194(11) 0.93510(10) 0.60123(8) 0.0159(2) Uani d . 1 . .
H H8A 0.8558 0.9432 0.6227 0.019 Uiso calc R 1 . .
H H8B 0.7223 1.0086 0.6190 0.019 Uiso calc R 1 . .
C C9 0.72673(11) 0.92265(11) 0.49385(8) 0.0162(2) Uani d . 1 . .
H H9A 0.6330 0.9132 0.4724 0.019 Uiso calc R 1 . .
H H9B 0.7516 0.9966 0.4659 0.019 Uiso calc R 1 . .
C C10 0.72954(11) 0.71504(11) 0.42958(8) 0.0160(2) Uani d . 1 . .
C C11 0.94356(12) 0.69048(12) 0.42409(9) 0.0210(3) Uani d . 1 . .
H H11A 0.9846 0.6861 0.3709 0.025 Uiso calc R 1 . .
H H11B 0.9977 0.6475 0.4771 0.025 Uiso calc R 1 . .
C C12 0.92429(11) 0.82316(11) 0.45003(8) 0.0170(3) Uani d . 1 . .
H H12A 0.9852 0.8466 0.5080 0.020 Uiso calc R 1 . .
H H12B 0.9329 0.8785 0.3998 0.020 Uiso calc R 1 . .
C C13 0.47432(11) 0.67173(11) 0.74094(8) 0.0156(2) Uani d . 1 . .
H H13A 0.4262 0.7430 0.7533 0.019 Uiso calc R 1 . .
H H13B 0.5050 0.6290 0.8002 0.019 Uiso calc R 1 . .
C C14 0.38313(11) 0.58849(11) 0.67225(8) 0.0169(2) Uani d . 1 . .
H H14A 0.4293 0.5147 0.6628 0.020 Uiso calc R 1 . .
H H14B 0.3102 0.5655 0.6989 0.020 Uiso calc R 1 . .
C C15 0.24555(11) 0.73773(11) 0.57032(8) 0.0159(2) Uani d . 1 . .
C C16 0.31809(12) 0.72690(11) 0.43458(9) 0.0198(3) Uani d . 1 . .
H H16A 0.3889 0.7837 0.4355 0.024 Uiso calc R 1 . .
H H16B 0.2794 0.7048 0.3697 0.024 Uiso calc R 1 . .
C C17 0.36658(12) 0.61423(11) 0.49327(8) 0.0197(3) Uani d . 1 . .
H H17A 0.3204 0.5413 0.4665 0.024 Uiso calc R 1 . .
H H17B 0.4596 0.6023 0.5006 0.024 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 O2 C11 . . 108.99(9) ?
C15 O4 C16 . . 107.65(9) ?
C1 N1 C2 . . 109.92(9) ?
C1 N1 C8 . . 122.48(10) ?
C2 N1 C8 . . 127.44(10) ?
C1 N2 C3 . . 109.94(9) ?
C1 N2 C13 . . 123.46(9) ?
C3 N2 C13 . . 126.51(10) ?
C10 N3 C9 . . 123.71(10) ?
C10 N3 C12 . . 112.52(10) ?
C9 N3 C12 . . 123.31(10) ?
C15 N4 C17 . . 112.04(10) ?
C15 N4 C14 . . 122.29(10) ?
C17 N4 C14 . . 125.49(10) ?
O1 C1 N2 . . 127.34(11) ?
O1 C1 N1 . . 126.44(11) ?
N2 C1 N1 . . 106.22(9) ?
C7 C2 N1 . . 131.76(11) ?
C7 C2 C3 . . 121.35(11) ?
N1 C2 C3 . . 106.88(10) ?
C4 C3 N2 . . 131.36(11) ?
C4 C3 C2 . . 121.60(11) ?
N2 C3 C2 . . 107.03(10) ?
C3 C4 C5 . . 116.91(11) ?
C3 C4 H4 . . 121.5 ?
C5 C4 H4 . . 121.5 ?
C6 C5 C4 . . 121.54(11) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
C5 C6 C7 . . 121.36(11) ?
C5 C6 H6 . . 119.3 ?
C7 C6 H6 . . 119.3 ?
C2 C7 C6 . . 117.21(11) ?
C2 C7 H7 . . 121.4 ?
C6 C7 H7 . . 121.4 ?
N1 C8 C9 . . 112.19(9) ?
N1 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
N1 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
N3 C9 C8 . . 112.07(9) ?
N3 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
N3 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O3 C10 N3 . . 128.03(11) ?
O3 C10 O2 . . 122.02(11) ?
N3 C10 O2 . . 109.95(10) ?
O2 C11 C12 . . 105.27(9) ?
O2 C11 H11A . . 110.7 ?
C12 C11 H11A . . 110.7 ?
O2 C11 H11B . . 110.7 ?
C12 C11 H11B . . 110.7 ?
H11A C11 H11B . . 108.8 ?
N3 C12 C11 . . 100.84(9) ?
N3 C12 H12A . . 111.6 ?
C11 C12 H12A . . 111.6 ?
N3 C12 H12B . . 111.6 ?
C11 C12 H12B . . 111.6 ?
H12A C12 H12B . . 109.4 ?
N2 C13 C14 . . 112.67(9) ?
N2 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
N2 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
N4 C14 C13 . . 111.20(10) ?
N4 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
N4 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
O5 C15 N4 . . 128.51(11) ?
O5 C15 O4 . . 121.68(11) ?
N4 C15 O4 . . 109.79(10) ?
O4 C16 C17 . . 104.61(9) ?
O4 C16 H16A . . 110.8 ?
C17 C16 H16A . . 110.8 ?
O4 C16 H16B . . 110.8 ?
C17 C16 H16B . . 110.8 ?
H16A C16 H16B . . 108.9 ?
N4 C17 C16 . . 99.92(9) ?
N4 C17 H17A . . 111.8 ?
C16 C17 H17A . . 111.8 ?
N4 C17 H17B . . 111.8 ?
C16 C17 H17B . . 111.8 ?
H17A C17 H17B . . 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
O1 C1 . 1.2252(14) ?
O2 C10 . 1.3612(14) ?
O2 C11 . 1.4510(15) ?
O3 C10 . 1.2144(14) ?
O4 C15 . 1.3692(14) ?
O4 C16 . 1.4531(14) ?
O5 C15 . 1.2147(14) ?
N1 C1 . 1.3862(15) ?
N1 C2 . 1.3926(15) ?
N1 C8 . 1.4545(15) ?
N2 C1 . 1.3831(15) ?
N2 C3 . 1.3921(15) ?
N2 C13 . 1.4570(14) ?
N3 C10 . 1.3439(16) ?
N3 C9 . 1.4496(15) ?
N3 C12 . 1.4552(14) ?
N4 C15 . 1.3396(15) ?
N4 C17 . 1.4542(15) ?
N4 C14 . 1.4546(15) ?
C2 C7 . 1.3853(16) ?
C2 C3 . 1.4027(16) ?
C3 C4 . 1.3862(17) ?
C4 C5 . 1.3971(17) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3927(17) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3955(17) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.5273(16) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C12 . 1.5282(17) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.5215(16) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C16 C17 . 1.5220(17) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656462
