#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229129.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_2229129
loop_
_publ_author_name
'Ouzidan, Younes'
'Kandri Rodi, Y.'
'Saffon, Natalie'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 1,3-Diallyl-5-chloro-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           JH2259
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o520
_journal_paper_doi               10.1107/S1600536811003035
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H13 Cl N2 O'
_chemical_formula_moiety         'C13 H13 Cl N2 O'
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70
_chemical_name_systematic
;
1,3-Diallyl-5-chloro-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                90.00
_cell_angle_beta                 93.0560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.88310(10)
_cell_length_b                   15.2481(3)
_cell_length_c                   10.3593(2)
_cell_measurement_reflns_used    4645
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      2.4
_cell_volume                     1243.44(4)
_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      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII'
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17723
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.9439
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0494
_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)+(0.0846P)²+0.6164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                2230
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2259.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229129
_cod_database_fobs_code          2229129
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
Cl Cl1 0.25390(9) 0.66457(5) 0.19928(6) 0.0609(2) Uani d . 1 . .
O O1 0.6243(2) 0.62064(10) 0.86933(14) 0.0468(4) Uani d . 1 . .
N N1 0.5616(2) 0.66732(10) 0.65711(15) 0.0341(4) Uani d . 1 . .
N N2 0.4252(2) 0.55197(10) 0.72844(15) 0.0340(4) Uani d . 1 . .
C C1 0.4530(2) 0.63903(12) 0.55655(17) 0.0304(4) Uani d . 1 . .
C C2 0.4221(2) 0.67167(12) 0.43253(18) 0.0346(4) Uani d . 1 . .
H H2 0.4781 0.7208 0.4029 0.042 Uiso calc R 1 . .
C C3 0.3021(3) 0.62631(14) 0.35525(19) 0.0388(5) Uani d . 1 . .
C C4 0.2168(3) 0.55288(14) 0.3964(2) 0.0407(5) Uani d . 1 . .
H H4 0.1391 0.5244 0.3403 0.049 Uiso calc R 1 . .
C C5 0.2476(2) 0.52151(13) 0.5227(2) 0.0371(4) Uani d . 1 . .
H H5 0.1904 0.4728 0.5526 0.045 Uiso calc R 1 . .
C C6 0.3663(2) 0.56580(12) 0.60094(17) 0.0307(4) Uani d . 1 . .
C C7 0.5461(3) 0.61349(12) 0.76399(18) 0.0348(4) Uani d . 1 . .
C C8 0.6889(3) 0.73629(13) 0.6498(2) 0.0385(5) Uani d . 1 . .
H H8A 0.7127 0.7607 0.7353 0.046 Uiso calc R 1 . .
H H8B 0.6442 0.7829 0.5941 0.046 Uiso calc R 1 . .
C C9 0.8507(3) 0.70238(14) 0.5983(2) 0.0438(5) Uani d . 1 . .
H H9 0.9055 0.6560 0.6414 0.053 Uiso calc R 1 . .
C C10 0.9186(3) 0.73440(16) 0.4965(3) 0.0548(6) Uani d . 1 . .
H H10A 0.8664 0.7808 0.4516 0.066 Uiso calc R 1 . .
H H10B 1.0192 0.7109 0.4687 0.066 Uiso calc R 1 . .
C C11 0.3710(3) 0.48204(13) 0.8125(2) 0.0410(5) Uani d . 1 . .
H H11A 0.4544 0.4757 0.8842 0.049 Uiso calc R 1 . .
H H11B 0.3681 0.4274 0.7645 0.049 Uiso calc R 1 . .
C C12 0.2008(3) 0.49716(17) 0.8649(2) 0.0561(7) Uani d . 1 . .
H H12 0.1536 0.4507 0.9088 0.067 Uiso calc R 1 . .
C C13 0.1120(4) 0.5692(2) 0.8550(3) 0.0647(8) Uani d . 1 . .
H H13A 0.1540 0.6174 0.8120 0.078 Uiso calc R 1 . .
H H13B 0.0066 0.5723 0.8911 0.078 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'
Cl Cl 0.1484 0.1585 '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 N1 C7 . . 109.83(16) ?
C1 N1 C8 . . 125.89(16) ?
C7 N1 C8 . . 123.90(17) ?
C7 N2 C6 . . 110.02(15) ?
C7 N2 C11 . . 124.17(17) ?
C6 N2 C11 . . 125.80(17) ?
N1 C1 C2 . . 131.12(17) ?
N1 C1 C6 . . 107.17(16) ?
C2 C1 C6 . . 121.71(18) ?
C3 C2 C1 . . 115.81(18) ?
C3 C2 H2 . . 122.1 ?
C1 C2 H2 . . 122.1 ?
C4 C3 C2 . . 123.46(19) ?
C4 C3 Cl1 . . 118.11(17) ?
C2 C3 Cl1 . . 118.43(16) ?
C3 C4 C5 . . 120.04(19) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 117.31(18) ?
C6 C5 H5 . . 121.3 ?
C4 C5 H5 . . 121.3 ?
C5 C6 N2 . . 131.58(17) ?
C5 C6 C1 . . 121.65(18) ?
N2 C6 C1 . . 106.76(16) ?
O1 C7 N2 . . 127.35(18) ?
O1 C7 N1 . . 126.44(18) ?
N2 C7 N1 . . 106.21(16) ?
N1 C8 C9 . . 111.75(16) ?
N1 C8 H8A . . 109.3 ?
C9 C8 H8A . . 109.3 ?
N1 C8 H8B . . 109.3 ?
C9 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
C10 C9 C8 . . 123.5(2) ?
C10 C9 H9 . . 118.2 ?
C8 C9 H9 . . 118.2 ?
C9 C10 H10A . . 120.0 ?
C9 C10 H10B . . 120.0 ?
H10A C10 H10B . . 120.0 ?
N2 C11 C12 . . 113.75(17) ?
N2 C11 H11A . . 108.8 ?
C12 C11 H11A . . 108.8 ?
N2 C11 H11B . . 108.8 ?
C12 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C11 . . 126.3(2) ?
C13 C12 H12 . . 116.9 ?
C11 C12 H12 . . 116.9 ?
C12 C13 H13A . . 120.0 ?
C12 C13 H13B . . 120.0 ?
H13A C13 H13B . . 120.0 ?
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
Cl1 C3 . 1.741(2) ?
O1 C7 . 1.229(2) ?
N1 C1 . 1.382(2) ?
N1 C7 . 1.389(2) ?
N1 C8 . 1.459(2) ?
N2 C7 . 1.373(3) ?
N2 C6 . 1.393(2) ?
N2 C11 . 1.455(2) ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.400(3) ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.385(3) ?
C4 C5 . 1.402(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C8 C9 . 1.501(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.303(3) ?
C9 H9 . 0.9300 ?
C10 H10A . 0.9300 ?
C10 H10B . 0.9300 ?
C11 C12 . 1.492(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.303(4) ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9300 ?
C13 H13B . 0.9300 ?
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
C7 N1 C1 C2 . . . . 179.23(19) ?
C8 N1 C1 C2 . . . . -7.7(3) ?
C7 N1 C1 C6 . . . . 0.2(2) ?
C8 N1 C1 C6 . . . . 173.33(17) ?
N1 C1 C2 C3 . . . . -179.86(18) ?
C6 C1 C2 C3 . . . . -1.0(3) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
C1 C2 C3 Cl1 . . . . 178.90(14) ?
C2 C3 C4 C5 . . . . 1.1(3) ?
Cl1 C3 C4 C5 . . . . -177.91(15) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
C4 C5 C6 N2 . . . . 179.97(18) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
C7 N2 C6 C5 . . . . 179.44(19) ?
C11 N2 C6 C5 . . . . 0.6(3) ?
C7 N2 C6 C1 . . . . -0.5(2) ?
C11 N2 C6 C1 . . . . -179.34(17) ?
N1 C1 C6 C5 . . . . -179.79(17) ?
C2 C1 C6 C5 . . . . 1.1(3) ?
N1 C1 C6 N2 . . . . 0.17(19) ?
C2 C1 C6 N2 . . . . -178.95(16) ?
C6 N2 C7 O1 . . . . 179.96(19) ?
C11 N2 C7 O1 . . . . -1.2(3) ?
C6 N2 C7 N1 . . . . 0.6(2) ?
C11 N2 C7 N1 . . . . 179.50(16) ?
C1 N1 C7 O1 . . . . -179.86(19) ?
C8 N1 C7 O1 . . . . 6.9(3) ?
C1 N1 C7 N2 . . . . -0.5(2) ?
C8 N1 C7 N2 . . . . -173.81(16) ?
C1 N1 C8 C9 . . . . -83.2(2) ?
C7 N1 C8 C9 . . . . 88.9(2) ?
N1 C8 C9 C10 . . . . 122.9(2) ?
C7 N2 C11 C12 . . . . 104.9(2) ?
C6 N2 C11 C12 . . . . -76.4(3) ?
N2 C11 C12 C13 . . . . -9.0(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3562359
