#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/95/2229568.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_2229568
loop_
_publ_author_name
'Ouzidan, Younes'
'Kandri Rodi, Y.'
'Ladeira, Sonia'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 1-n-Decyl-5-nitro-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           ZS2093
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o613
_journal_paper_doi               10.1107/S1600536811004399
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H25 N3 O3'
_chemical_formula_moiety         'C17 H25 N3 O3'
_chemical_formula_sum            'C17 H25 N3 O3'
_chemical_formula_weight         319.40
_chemical_name_systematic
;
1-n-decyl-5-nitro-1H-benzimidazol-2(3H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.504(2)
_cell_angle_beta                 98.545(2)
_cell_angle_gamma                96.809(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4933(2)
_cell_length_b                   10.3063(4)
_cell_length_c                   16.1655(6)
_cell_measurement_reflns_used    1521
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.7
_cell_volume                     855.21(6)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII'
_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  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10701
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.309
_refine_ls_extinction_coef       0.034(6)
_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   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0548
_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)+(0.1056P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                1600
_reflns_number_total             2971
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2093.cif
_cod_data_source_block           I
_cod_database_code               2229568
_cod_database_fobs_code          2229568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.6868(3) 0.57512(19) 0.61197(12) 0.0413(6) Uani d . 1 . .
O O2 0.8896(4) -0.0690(2) 0.29737(16) 0.0579(7) Uani d . 1 . .
O O3 1.2510(4) -0.0845(2) 0.36526(16) 0.0680(7) Uani d . 1 . .
N N1 0.7157(4) 0.3830(2) 0.49844(15) 0.0357(6) Uani d . 1 . .
H H1 0.5863 0.3832 0.4592 0.043 Uiso calc R 1 . .
N N2 0.9999(4) 0.4426(2) 0.61946(15) 0.0337(6) Uani d . 1 . .
N N3 1.0691(5) -0.0264(2) 0.35868(19) 0.0482(7) Uani d . 1 . .
C C1 0.7879(5) 0.4765(3) 0.57918(19) 0.0354(7) Uani d . 1 . .
C C2 0.8734(5) 0.2871(3) 0.48616(18) 0.0328(7) Uani d . 1 . .
C C3 0.8717(5) 0.1718(3) 0.41760(19) 0.0371(7) Uani d . 1 . .
H H3 0.7483 0.1435 0.3671 0.044 Uiso calc R 1 . .
C C4 1.0672(5) 0.1002(3) 0.4288(2) 0.0380(7) Uani d . 1 . .
C C5 1.2516(5) 0.1396(3) 0.5022(2) 0.0397(8) Uani d . 1 . .
H H5 1.3801 0.0890 0.5052 0.048 Uiso calc R 1 . .
C C6 1.2493(5) 0.2538(3) 0.5717(2) 0.0385(7) Uani d . 1 . .
H H6 1.3723 0.2805 0.6223 0.046 Uiso calc R 1 . .
C C7 1.0566(5) 0.3268(3) 0.56298(19) 0.0347(7) Uani d . 1 . .
C C8 1.1434(5) 0.5230(3) 0.70567(18) 0.0399(7) Uani d . 1 . .
H H8A 1.0786 0.6078 0.7254 0.048 Uiso calc R 1 . .
H H8B 1.3157 0.5469 0.7007 0.048 Uiso calc R 1 . .
C C9 1.1361(5) 0.4479(3) 0.77434(19) 0.0420(7) Uani d . 1 . .
H H9A 1.1954 0.3618 0.7530 0.050 Uiso calc R 1 . .
H H9B 1.2519 0.5027 0.8276 0.050 Uiso calc R 1 . .
C C10 0.8830(5) 0.4174(3) 0.7976(2) 0.0457(8) Uani d . 1 . .
H H10A 0.7678 0.3575 0.7457 0.055 Uiso calc R 1 . .
H H10B 0.8185 0.5023 0.8171 0.055 Uiso calc R 1 . .
C C11 0.8982(5) 0.3489(3) 0.8699(2) 0.0463(8) Uani d . 1 . .
H H11A 0.9593 0.2632 0.8491 0.056 Uiso calc R 1 . .
H H11B 1.0202 0.4076 0.9204 0.056 Uiso calc R 1 . .
C C12 0.6562(6) 0.3190(3) 0.8998(2) 0.0516(9) Uani d . 1 . .
H H12A 0.5896 0.4036 0.9179 0.062 Uiso calc R 1 . .
H H12B 0.5366 0.2556 0.8505 0.062 Uiso calc R 1 . .
C C13 0.6824(6) 0.2585(3) 0.9749(2) 0.0492(8) Uani d . 1 . .
H H13A 0.8060 0.3210 1.0234 0.059 Uiso calc R 1 . .
H H13B 0.7457 0.1731 0.9561 0.059 Uiso calc R 1 . .
C C14 0.4445(6) 0.2305(3) 1.0082(2) 0.0535(9) Uani d . 1 . .
H H14A 0.3754 0.3146 1.0235 0.064 Uiso calc R 1 . .
H H14B 0.3244 0.1634 0.9608 0.064 Uiso calc R 1 . .
C C15 0.4751(6) 0.1780(3) 1.0874(2) 0.0531(9) Uani d . 1 . .
H H15A 0.5400 0.0926 1.0717 0.064 Uiso calc R 1 . .
H H15B 0.5981 0.2439 1.1344 0.064 Uiso calc R 1 . .
C C16 0.2378(7) 0.1537(4) 1.1214(2) 0.0692(11) Uani d . 1 . .
H H16A 0.1189 0.0825 1.0760 0.083 Uiso calc R 1 . .
H H16B 0.1659 0.2371 1.1331 0.083 Uiso calc R 1 . .
C C17 0.2764(8) 0.1116(4) 1.2043(3) 0.0862(13) Uani d . 1 . .
H H17A 0.1189 0.0965 1.2220 0.129 Uiso calc R 1 . .
H H17B 0.3888 0.1832 1.2503 0.129 Uiso calc R 1 . .
H H17C 0.3460 0.0286 1.1932 0.129 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'
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 C2 . . 110.5(2) ?
C1 N1 H1 . . 124.7 ?
C2 N1 H1 . . 124.7 ?
C1 N2 C7 . . 109.0(2) ?
C1 N2 C8 . . 124.0(2) ?
C7 N2 C8 . . 126.9(2) ?
O2 N3 O3 . . 123.7(3) ?
O2 N3 C4 . . 118.5(2) ?
O3 N3 C4 . . 117.8(3) ?
O1 C1 N1 . . 127.5(3) ?
O1 C1 N2 . . 125.5(3) ?
N1 C1 N2 . . 107.0(2) ?
C3 C2 N1 . . 132.1(3) ?
C3 C2 C7 . . 121.8(2) ?
N1 C2 C7 . . 106.1(2) ?
C2 C3 C4 . . 115.5(3) ?
C2 C3 H3 . . 122.3 ?
C4 C3 H3 . . 122.3 ?
C5 C4 C3 . . 123.6(3) ?
C5 C4 N3 . . 118.8(3) ?
C3 C4 N3 . . 117.6(3) ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 117.2(3) ?
C7 C6 H6 . . 121.4 ?
C5 C6 H6 . . 121.4 ?
N2 C7 C6 . . 131.5(3) ?
N2 C7 C2 . . 107.3(2) ?
C6 C7 C2 . . 121.2(3) ?
N2 C8 C9 . . 113.2(2) ?
N2 C8 H8A . . 108.9 ?
C9 C8 H8A . . 108.9 ?
N2 C8 H8B . . 108.9 ?
C9 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C8 . . 115.7(2) ?
C10 C9 H9A . . 108.4 ?
C8 C9 H9A . . 108.4 ?
C10 C9 H9B . . 108.4 ?
C8 C9 H9B . . 108.4 ?
H9A C9 H9B . . 107.4 ?
C9 C10 C11 . . 111.6(2) ?
C9 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
C9 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 115.4(2) ?
C12 C11 H11A . . 108.4 ?
C10 C11 H11A . . 108.4 ?
C12 C11 H11B . . 108.4 ?
C10 C11 H11B . . 108.4 ?
H11A C11 H11B . . 107.5 ?
C13 C12 C11 . . 113.7(2) ?
C13 C12 H12A . . 108.8 ?
C11 C12 H12A . . 108.8 ?
C13 C12 H12B . . 108.8 ?
C11 C12 H12B . . 108.8 ?
H12A C12 H12B . . 107.7 ?
C12 C13 C14 . . 115.2(2) ?
C12 C13 H13A . . 108.5 ?
C14 C13 H13A . . 108.5 ?
C12 C13 H13B . . 108.5 ?
C14 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C15 C14 C13 . . 115.0(3) ?
C15 C14 H14A . . 108.5 ?
C13 C14 H14A . . 108.5 ?
C15 C14 H14B . . 108.5 ?
C13 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
C16 C15 C14 . . 114.5(3) ?
C16 C15 H15A . . 108.6 ?
C14 C15 H15A . . 108.6 ?
C16 C15 H15B . . 108.6 ?
C14 C15 H15B . . 108.6 ?
H15A C15 H15B . . 107.6 ?
C15 C16 C17 . . 113.5(3) ?
C15 C16 H16A . . 108.9 ?
C17 C16 H16A . . 108.9 ?
C15 C16 H16B . . 108.9 ?
C17 C16 H16B . . 108.9 ?
H16A C16 H16B . . 107.7 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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 . 1.240(3) ?
O2 N3 . 1.228(3) ?
O3 N3 . 1.231(3) ?
N1 C1 . 1.353(3) ?
N1 C2 . 1.382(3) ?
N1 H1 . 0.8800 ?
N2 C1 . 1.379(3) ?
N2 C7 . 1.382(3) ?
N2 C8 . 1.454(4) ?
N3 C4 . 1.468(4) ?
C2 C3 . 1.374(4) ?
C2 C7 . 1.402(4) ?
C3 C4 . 1.391(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(4) ?
C5 C6 . 1.380(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.382(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.526(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.514(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.525(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.508(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.511(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.513(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.520(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.509(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.517(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
N1 H1 O1 2_666 0.88 1.92 2.784(3) 168
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 O1 . . . . -179.0(2) ?
C2 N1 C1 N2 . . . . 1.4(3) ?
C7 N2 C1 O1 . . . . 180.0(2) ?
C8 N2 C1 O1 . . . . -3.2(4) ?
C7 N2 C1 N1 . . . . -0.4(3) ?
C8 N2 C1 N1 . . . . 176.4(2) ?
C1 N1 C2 C3 . . . . 177.4(3) ?
C1 N1 C2 C7 . . . . -1.7(3) ?
N1 C2 C3 C4 . . . . 179.3(2) ?
C7 C2 C3 C4 . . . . -1.7(4) ?
C2 C3 C4 C5 . . . . -0.3(4) ?
C2 C3 C4 N3 . . . . 178.0(2) ?
O2 N3 C4 C5 . . . . 172.5(2) ?
O3 N3 C4 C5 . . . . -7.0(4) ?
O2 N3 C4 C3 . . . . -5.8(4) ?
O3 N3 C4 C3 . . . . 174.7(2) ?
C3 C4 C5 C6 . . . . 1.8(4) ?
N3 C4 C5 C6 . . . . -176.5(2) ?
C4 C5 C6 C7 . . . . -1.2(4) ?
C1 N2 C7 C6 . . . . 179.2(3) ?
C8 N2 C7 C6 . . . . 2.5(4) ?
C1 N2 C7 C2 . . . . -0.7(3) ?
C8 N2 C7 C2 . . . . -177.4(2) ?
C5 C6 C7 N2 . . . . 179.3(3) ?
C5 C6 C7 C2 . . . . -0.8(4) ?
C3 C2 C7 N2 . . . . -177.8(2) ?
N1 C2 C7 N2 . . . . 1.4(3) ?
C3 C2 C7 C6 . . . . 2.3(4) ?
N1 C2 C7 C6 . . . . -178.4(2) ?
C1 N2 C8 C9 . . . . 114.0(3) ?
C7 N2 C8 C9 . . . . -69.7(3) ?
N2 C8 C9 C10 . . . . -65.3(3) ?
C8 C9 C10 C11 . . . . -177.1(2) ?
C9 C10 C11 C12 . . . . 177.9(3) ?
C10 C11 C12 C13 . . . . -176.8(3) ?
C11 C12 C13 C14 . . . . 178.5(3) ?
C12 C13 C14 C15 . . . . -176.4(3) ?
C13 C14 C15 C16 . . . . 178.6(3) ?
C14 C15 C16 C17 . . . . -175.7(3) ?
