#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229384.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_2229384
loop_
_publ_author_name
'Ouzidan, Younes'
'Kandri Rodi, Youssef'
'Essassi, El Mokhtar'
'El Ammari, Lahcen'
'Fronczek, Frank R.'
'Venkatraman, Ramaiyer'
_publ_section_title
;
 5-Nitro-1-nonyl-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           GK2342
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o669
_journal_paper_doi               10.1107/S1600536811005654
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H23 N3 O3'
_chemical_formula_moiety         'C16 H23 N3 O3'
_chemical_formula_sum            'C16 H23 N3 O3'
_chemical_formula_weight         305.37
_chemical_name_systematic
;
5-Nitro-1-nonyl-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                74.275(9)
_cell_angle_beta                 79.727(6)
_cell_angle_gamma                83.410(8)
_cell_formula_units_Z            2
_cell_length_a                   5.4830(10)
_cell_length_b                   10.2092(15)
_cell_length_c                   14.746(3)
_cell_measurement_reflns_used    5537
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      34.9
_cell_measurement_theta_min      2.5
_cell_volume                     779.9(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_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  0.023
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21087
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.9
_diffrn_reflns_theta_min         2.8
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.276
_refine_ls_extinction_coef       0.023(5)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         6349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0404
_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)+(0.0578P)²+0.1462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                5183
_reflns_number_total             6349
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2342.cif
_cod_data_source_block           I
_cod_database_code               2229384
_cod_database_fobs_code          2229384
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 0.92795(11) 1.07035(6) 0.37556(4) 0.01618(12) Uani d . 1 . .
O O2 0.40529(12) 0.45052(6) 0.71989(4) 0.02109(13) Uani d . 1 . .
O O3 0.12666(12) 0.41865(6) 0.64166(5) 0.02143(13) Uani d . 1 . .
N N1 0.78463(12) 0.88673(7) 0.50035(5) 0.01369(12) Uani d . 1 . .
H H1 0.8751 0.8904 0.5431 0.016 Uiso calc R 1 . .
N N2 0.61923(12) 0.93607(7) 0.36748(4) 0.01292(12) Uani d . 1 . .
N N3 0.29292(13) 0.48382(7) 0.65097(5) 0.01591(13) Uani d . 1 . .
C C1 0.79248(13) 0.97452(8) 0.41127(5) 0.01294(13) Uani d . 1 . .
C C2 0.50448(13) 0.82444(7) 0.42883(5) 0.01255(13) Uani d . 1 . .
C C3 0.61268(13) 0.79137(8) 0.51286(5) 0.01240(13) Uani d . 1 . .
C C4 0.54726(13) 0.68061(8) 0.58770(5) 0.01379(13) Uani d . 1 . .
H H4 0.6229 0.6565 0.6437 0.017 Uiso calc R 1 . .
C C5 0.36219(13) 0.60623(7) 0.57568(5) 0.01384(13) Uani d . 1 . .
C C6 0.24677(14) 0.63920(8) 0.49481(6) 0.01500(13) Uani d . 1 . .
H H6 0.1193 0.5860 0.4912 0.018 Uiso calc R 1 . .
C C7 0.31799(14) 0.75013(8) 0.41917(5) 0.01431(13) Uani d . 1 . .
H H7 0.2421 0.7740 0.3632 0.017 Uiso calc R 1 . .
C C8 0.56136(14) 1.00911(8) 0.27295(5) 0.01453(13) Uani d . 1 . .
H H8A 0.6475 1.0948 0.2508 0.017 Uiso calc R 1 . .
H H8B 0.3804 1.0338 0.2778 0.017 Uiso calc R 1 . .
C C9 0.63787(14) 0.92606(8) 0.19926(5) 0.01496(13) Uani d . 1 . .
H H9A 0.5714 0.9758 0.1402 0.018 Uiso calc R 1 . .
H H9B 0.5589 0.8382 0.2237 0.018 Uiso calc R 1 . .
C C10 0.91760(14) 0.89612(8) 0.17380(5) 0.01536(14) Uani d . 1 . .
H H10A 0.9848 0.8397 0.2311 0.018 Uiso calc R 1 . .
H H10B 1.0005 0.9829 0.1522 0.018 Uiso calc R 1 . .
C C11 0.97314(15) 0.82089(8) 0.09493(6) 0.01648(14) Uani d . 1 . .
H H11A 0.8959 0.7325 0.1186 0.020 Uiso calc R 1 . .
H H11B 0.8936 0.8751 0.0400 0.020 Uiso calc R 1 . .
C C12 1.24889(15) 0.79376(8) 0.06003(6) 0.01714(14) Uani d . 1 . .
H H12A 1.3281 0.7349 0.1137 0.021 Uiso calc R 1 . .
H H12B 1.3293 0.8813 0.0386 0.021 Uiso calc R 1 . .
C C13 1.29159(14) 0.72462(8) -0.02204(6) 0.01650(14) Uani d . 1 . .
H H13A 1.2188 0.6349 0.0010 0.020 Uiso calc R 1 . .
H H13B 1.2018 0.7809 -0.0735 0.020 Uiso calc R 1 . .
C C14 1.56428(15) 0.70296(8) -0.06374(6) 0.01707(14) Uani d . 1 . .
H H14A 1.6346 0.7928 -0.0918 0.020 Uiso calc R 1 . .
H H14B 1.6575 0.6522 -0.0118 0.020 Uiso calc R 1 . .
C C15 1.59873(15) 0.62433(9) -0.14015(6) 0.01812(15) Uani d . 1 . .
H H15A 1.5350 0.5330 -0.1111 0.022 Uiso calc R 1 . .
H H15B 1.4981 0.6728 -0.1903 0.022 Uiso calc R 1 . .
C C16 1.86819(17) 0.60708(10) -0.18635(7) 0.02506(18) Uani d . 1 . .
H H16A 1.9271 0.6967 -0.2215 0.038 Uiso calc R 1 . .
H H16B 1.8795 0.5492 -0.2304 0.038 Uiso calc R 1 . .
H H16C 1.9712 0.5643 -0.1368 0.038 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 C3 . . 109.78(6) ?
C1 N1 H1 . . 125.1 ?
C3 N1 H1 . . 125.1 ?
C1 N2 C2 . . 109.39(6) ?
C1 N2 C8 . . 124.01(6) ?
C2 N2 C8 . . 126.52(6) ?
O2 N3 O3 . . 123.41(7) ?
O2 N3 C5 . . 118.20(7) ?
O3 N3 C5 . . 118.39(7) ?
O1 C1 N1 . . 127.21(7) ?
O1 C1 N2 . . 125.74(7) ?
N1 C1 N2 . . 107.04(6) ?
N2 C2 C7 . . 131.59(7) ?
N2 C2 C3 . . 106.99(6) ?
C7 C2 C3 . . 121.42(7) ?
C4 C3 N1 . . 131.24(7) ?
C4 C3 C2 . . 121.98(7) ?
N1 C3 C2 . . 106.77(6) ?
C3 C4 C5 . . 115.49(7) ?
C3 C4 H4 . . 122.3 ?
C5 C4 H4 . . 122.3 ?
C6 C5 C4 . . 123.69(7) ?
C6 C5 N3 . . 118.32(7) ?
C4 C5 N3 . . 117.95(7) ?
C5 C6 C7 . . 120.08(7) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C2 C7 C6 . . 117.29(7) ?
C2 C7 H7 . . 121.4 ?
C6 C7 H7 . . 121.4 ?
N2 C8 C9 . . 113.04(6) ?
N2 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
N2 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C10 . . 115.31(6) ?
C8 C9 H9A . . 108.4 ?
C10 C9 H9A . . 108.4 ?
C8 C9 H9B . . 108.4 ?
C10 C9 H9B . . 108.4 ?
H9A C9 H9B . . 107.5 ?
C9 C10 C11 . . 110.76(6) ?
C9 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C12 C11 C10 . . 114.85(6) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.5 ?
C11 C12 C13 . . 112.22(6) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 114.38(7) ?
C14 C13 H13A . . 108.7 ?
C12 C13 H13A . . 108.7 ?
C14 C13 H13B . . 108.7 ?
C12 C13 H13B . . 108.7 ?
H13A C13 H13B . . 107.6 ?
C15 C14 C13 . . 112.45(7) ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.8 ?
C16 C15 C14 . . 113.56(7) ?
C16 C15 H15A . . 108.9 ?
C14 C15 H15A . . 108.9 ?
C16 C15 H15B . . 108.9 ?
C14 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 . 1.2387(9) ?
O2 N3 . 1.2313(9) ?
O3 N3 . 1.2352(9) ?
N1 C1 . 1.3715(10) ?
N1 C3 . 1.3864(9) ?
N1 H1 . 0.8800 ?
N2 C1 . 1.3838(10) ?
N2 C2 . 1.3842(10) ?
N2 C8 . 1.4628(10) ?
N3 C5 . 1.4646(10) ?
C2 C7 . 1.3893(10) ?
C2 C3 . 1.4109(10) ?
C3 C4 . 1.3787(11) ?
C4 C5 . 1.3970(11) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3924(11) ?
C6 C7 . 1.3930(11) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.5266(11) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5284(11) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5297(11) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.5268(11) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5303(11) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.5272(11) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.5263(11) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.5246(12) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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_776 0.88 1.89 2.7651(9) 170
C6 H6 O3 2_566 0.95 2.58 3.3139(11) 134
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
C3 N1 C1 O1 . . . . -178.59(7) ?
C3 N1 C1 N2 . . . . 1.29(8) ?
C2 N2 C1 O1 . . . . 179.64(7) ?
C8 N2 C1 O1 . . . . -3.45(12) ?
C2 N2 C1 N1 . . . . -0.24(8) ?
C8 N2 C1 N1 . . . . 176.67(6) ?
C1 N2 C2 C7 . . . . 178.96(8) ?
C8 N2 C2 C7 . . . . 2.15(13) ?
C1 N2 C2 C3 . . . . -0.87(8) ?
C8 N2 C2 C3 . . . . -177.68(6) ?
C1 N1 C3 C4 . . . . 176.91(8) ?
C1 N1 C3 C2 . . . . -1.82(8) ?
N2 C2 C3 C4 . . . . -177.25(7) ?
C7 C2 C3 C4 . . . . 2.90(11) ?
N2 C2 C3 N1 . . . . 1.62(8) ?
C7 C2 C3 N1 . . . . -178.23(7) ?
N1 C3 C4 C5 . . . . 179.65(7) ?
C2 C3 C4 C5 . . . . -1.79(11) ?
C3 C4 C5 C6 . . . . -0.32(11) ?
C3 C4 C5 N3 . . . . 177.28(6) ?
O2 N3 C5 C6 . . . . 175.91(7) ?
O3 N3 C5 C6 . . . . -3.41(11) ?
O2 N3 C5 C4 . . . . -1.82(10) ?
O3 N3 C5 C4 . . . . 178.86(7) ?
C4 C5 C6 C7 . . . . 1.40(12) ?
N3 C5 C6 C7 . . . . -176.19(7) ?
N2 C2 C7 C6 . . . . 178.47(7) ?
C3 C2 C7 C6 . . . . -1.72(11) ?
C5 C6 C7 C2 . . . . -0.33(11) ?
C1 N2 C8 C9 . . . . 113.65(8) ?
C2 N2 C8 C9 . . . . -69.97(9) ?
N2 C8 C9 C10 . . . . -66.44(9) ?
C8 C9 C10 C11 . . . . -176.26(6) ?
C9 C10 C11 C12 . . . . 176.47(7) ?
C10 C11 C12 C13 . . . . -177.19(7) ?
C11 C12 C13 C14 . . . . 176.46(7) ?
C12 C13 C14 C15 . . . . 175.71(7) ?
C13 C14 C15 C16 . . . . 177.26(7) ?
