#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/63/2236369.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_2236369
loop_
_publ_author_name
'Belaziz, Dounia'
'Kandri Rodi, Youssef'
'Ouazzani Chahdi, Fouad'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_contact_author
;
Dounia Belaziz
Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed
Ben Abdallah, Faculté des Sciences et Techniques, Route d'immouzzer,
BP 2202  Fès, Morocco.
;
_publ_section_title
;
 1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one
;
_journal_coeditor_code           IM2402
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3069
_journal_paper_doi               10.1107/S1600536812041189
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H30 N2 O'
_chemical_formula_moiety         'C19 H30 N2 O'
_chemical_formula_sum            'C19 H30 N2 O'
_chemical_formula_weight         302.45
_chemical_melting_point          346.5
_chemical_name_systematic
;
1-Dodecyl-1H-benzo[d]imidazol-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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.843(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   38.3223(14)
_cell_length_b                   4.8318(2)
_cell_length_c                   21.9831(8)
_cell_measurement_reflns_used    4637
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      2.4
_cell_volume                     3599.3(2)
_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
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX 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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29002
_diffrn_reflns_theta_full        28.65
_diffrn_reflns_theta_max         28.65
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0450
_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)+(0.0721P)²+1.0300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                3179
_reflns_number_total             4637
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            im2402.cif
_cod_data_source_block           I
_cod_database_code               2236369
_cod_database_fobs_code          2236369
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_symmetry_multiplicity
N N2 0.03233(3) 0.5579(2) 0.13178(5) 0.0394(2) Uani d . 1 1
N N1 -0.01601(3) 0.7314(2) 0.03782(5) 0.0398(2) Uani d . 1 1
H H1 -0.0289 0.8297 0.0014 0.048 Uiso calc R 1 1
O O1 0.04750(2) 0.91076(19) 0.07646(4) 0.0472(2) Uani d . 1 1
C C11 0.13888(4) 0.6345(3) 0.37748(6) 0.0440(3) Uani d . 1 1
H H11A 0.1187 0.6113 0.3920 0.053 Uiso calc R 1 1
H H11B 0.1428 0.8315 0.3747 0.053 Uiso calc R 1 1
C C7 -0.00182(3) 0.4187(2) 0.12105(6) 0.0386(3) Uani d . 1 1
C C9 0.08398(3) 0.6105(3) 0.25353(6) 0.0431(3) Uani d . 1 1
H H9A 0.0644 0.5596 0.2679 0.052 Uiso calc R 1 1
H H9B 0.0844 0.8108 0.2510 0.052 Uiso calc R 1 1
C C15 0.24328(4) 0.5988(3) 0.62951(6) 0.0514(3) Uani d . 1 1
H H15A 0.2457 0.7986 0.6294 0.062 Uiso calc R 1 1
H H15B 0.2233 0.5564 0.6435 0.062 Uiso calc R 1 1
C C12 0.17715(4) 0.5077(3) 0.43133(6) 0.0484(3) Uani d . 1 1
H H12A 0.1737 0.3089 0.4317 0.058 Uiso calc R 1 1
H H12B 0.1977 0.5418 0.4182 0.058 Uiso calc R 1 1
C C1 0.02366(3) 0.7522(2) 0.08097(5) 0.0371(3) Uani d . 1 1
C C13 0.19082(4) 0.6180(3) 0.50358(6) 0.0498(3) Uani d . 1 1
H H13A 0.1705 0.5816 0.5171 0.060 Uiso calc R 1 1
H H13B 0.1940 0.8170 0.5032 0.060 Uiso calc R 1 1
C C8 0.07235(3) 0.4891(3) 0.18297(6) 0.0424(3) Uani d . 1 1
H H8A 0.0906 0.5557 0.1671 0.051 Uiso calc R 1 1
H H8B 0.0749 0.2894 0.1870 0.051 Uiso calc R 1 1
C C2 -0.03246(3) 0.5297(2) 0.06114(6) 0.0383(3) Uani d . 1 1
C C10 0.12435(4) 0.5075(3) 0.30657(6) 0.0463(3) Uani d . 1 1
H H10A 0.1232 0.3081 0.3104 0.056 Uiso calc R 1 1
H H10B 0.1433 0.5476 0.2902 0.056 Uiso calc R 1 1
C C17 0.29647(4) 0.5852(3) 0.75462(6) 0.0513(3) Uani d . 1 1
H H17A 0.2983 0.7854 0.7541 0.062 Uiso calc R 1 1
H H17B 0.2769 0.5392 0.7693 0.062 Uiso calc R 1 1
C C14 0.22938(4) 0.4922(3) 0.55680(6) 0.0517(3) Uani d . 1 1
H H14A 0.2497 0.5298 0.5433 0.062 Uiso calc R 1 1
H H14B 0.2262 0.2930 0.5567 0.062 Uiso calc R 1 1
C C16 0.28233(4) 0.4785(3) 0.68205(6) 0.0522(3) Uani d . 1 1
H H16A 0.2798 0.2788 0.6823 0.063 Uiso calc R 1 1
H H16B 0.3022 0.5199 0.6678 0.063 Uiso calc R 1 1
C C6 -0.00851(4) 0.2120(3) 0.15747(7) 0.0493(3) Uani d . 1 1
H H6 0.0118 0.1406 0.1977 0.059 Uiso calc R 1 1
C C3 -0.07051(4) 0.4301(3) 0.03570(7) 0.0490(3) Uani d . 1 1
H H3 -0.0910 0.5015 -0.0044 0.059 Uiso calc R 1 1
C C5 -0.04689(4) 0.1145(3) 0.13174(7) 0.0553(4) Uani d . 1 1
H H5 -0.0524 -0.0248 0.1552 0.066 Uiso calc R 1 1
C C18 0.33590(4) 0.4716(3) 0.80666(7) 0.0616(4) Uani d . 1 1
H H18A 0.3555 0.5176 0.7921 0.074 Uiso calc R 1 1
H H18B 0.3341 0.2714 0.8072 0.074 Uiso calc R 1 1
C C19 0.34981(5) 0.5790(4) 0.87888(7) 0.0774(5) Uani d . 1 1
H H19A 0.3750 0.4990 0.9090 0.116 Uiso calc R 1 1
H H19B 0.3310 0.5294 0.8944 0.116 Uiso calc R 1 1
H H19C 0.3522 0.7768 0.8791 0.116 Uiso calc R 1 1
C C4 -0.07710(4) 0.2207(3) 0.07186(8) 0.0554(4) Uani d . 1 1
H H4 -0.1024 0.1494 0.0556 0.066 Uiso calc R 1 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
C1 N2 C7 109.94(9)
C1 N2 C8 123.45(10)
C7 N2 C8 126.15(10)
C1 N1 C2 110.23(9)
C1 N1 H1 124.9
C2 N1 H1 124.9
C10 C11 C12 113.25(11)
C10 C11 H11A 108.9
C12 C11 H11A 108.9
C10 C11 H11B 108.9
C12 C11 H11B 108.9
H11A C11 H11B 107.7
C6 C7 N2 131.94(11)
C6 C7 C2 121.55(11)
N2 C7 C2 106.51(10)
C8 C9 C10 111.39(10)
C8 C9 H9A 109.3
C10 C9 H9A 109.3
C8 C9 H9B 109.3
C10 C9 H9B 109.3
H9A C9 H9B 108.0
C16 C15 C14 114.07(12)
C16 C15 H15A 108.7
C14 C15 H15A 108.7
C16 C15 H15B 108.7
C14 C15 H15B 108.7
H15A C15 H15B 107.6
C13 C12 C11 114.18(11)
C13 C12 H12A 108.7
C11 C12 H12A 108.7
C13 C12 H12B 108.7
C11 C12 H12B 108.7
H12A C12 H12B 107.6
O1 C1 N1 127.98(10)
O1 C1 N2 125.67(10)
N1 C1 N2 106.35(10)
C12 C13 C14 113.68(12)
C12 C13 H13A 108.8
C14 C13 H13A 108.8
C12 C13 H13B 108.8
C14 C13 H13B 108.8
H13A C13 H13B 107.7
N2 C8 C9 113.73(10)
N2 C8 H8A 108.8
C9 C8 H8A 108.8
N2 C8 H8B 108.8
C9 C8 H8B 108.8
H8A C8 H8B 107.7
C3 C2 N1 132.32(11)
C3 C2 C7 120.71(12)
N1 C2 C7 106.97(10)
C11 C10 C9 114.11(11)
C11 C10 H10A 108.7
C9 C10 H10A 108.7
C11 C10 H10B 108.7
C9 C10 H10B 108.7
H10A C10 H10B 107.6
C18 C17 C16 114.41(12)
C18 C17 H17A 108.7
C16 C17 H17A 108.7
C18 C17 H17B 108.7
C16 C17 H17B 108.7
H17A C17 H17B 107.6
C13 C14 C15 114.31(12)
C13 C14 H14A 108.7
C15 C14 H14A 108.7
C13 C14 H14B 108.7
C15 C14 H14B 108.7
H14A C14 H14B 107.6
C17 C16 C15 114.33(12)
C17 C16 H16A 108.7
C15 C16 H16A 108.7
C17 C16 H16B 108.7
C15 C16 H16B 108.7
H16A C16 H16B 107.6
C7 C6 C5 117.30(12)
C7 C6 H6 121.3
C5 C6 H6 121.3
C4 C3 C2 117.68(12)
C4 C3 H3 121.2
C2 C3 H3 121.2
C4 C5 C6 121.22(13)
C4 C5 H5 119.4
C6 C5 H5 119.4
C17 C18 C19 114.10(14)
C17 C18 H18A 108.7
C19 C18 H18A 108.7
C17 C18 H18B 108.7
C19 C18 H18B 108.7
H18A C18 H18B 107.6
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C3 C4 C5 121.52(13)
C3 C4 H4 119.2
C5 C4 H4 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C1 1.3759(15)
N2 C7 1.3899(15)
N2 C8 1.4550(14)
N1 C1 1.3688(14)
N1 C2 1.3827(15)
N1 H1 0.8600
O1 C1 1.2314(14)
C11 C10 1.5184(16)
C11 C12 1.5187(16)
C11 H11A 0.9700
C11 H11B 0.9700
C7 C6 1.3771(18)
C7 C2 1.3986(16)
C9 C8 1.5177(16)
C9 C10 1.5218(16)
C9 H9A 0.9700
C9 H9B 0.9700
C15 C16 1.5157(18)
C15 C14 1.5195(18)
C15 H15A 0.9700
C15 H15B 0.9700
C12 C13 1.5180(17)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.5186(17)
C13 H13A 0.9700
C13 H13B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C2 C3 1.3816(17)
C10 H10A 0.9700
C10 H10B 0.9700
C17 C18 1.5095(18)
C17 C16 1.5156(18)
C17 H17A 0.9700
C17 H17B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C16 H16A 0.9700
C16 H16B 0.9700
C6 C5 1.3885(19)
C6 H6 0.9300
C3 C4 1.381(2)
C3 H3 0.9300
C5 C4 1.383(2)
C5 H5 0.9300
C18 C19 1.511(2)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C4 H4 0.9300
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 5_575 0.86 1.97 2.8150(10) 168.1
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
C1 N2 C7 C6 -179.18(12)
C8 N2 C7 C6 8.5(2)
C1 N2 C7 C2 0.61(13)
C8 N2 C7 C2 -171.76(10)
C10 C11 C12 C13 -176.14(11)
C2 N1 C1 O1 -179.33(11)
C2 N1 C1 N2 0.70(12)
C7 N2 C1 O1 179.22(11)
C8 N2 C1 O1 -8.16(18)
C7 N2 C1 N1 -0.81(12)
C8 N2 C1 N1 171.81(10)
C11 C12 C13 C14 -179.29(11)
C1 N2 C8 C9 104.30(13)
C7 N2 C8 C9 -84.31(15)
C10 C9 C8 N2 174.01(10)
C1 N1 C2 C3 -179.08(12)
C1 N1 C2 C7 -0.33(13)
C6 C7 C2 C3 -1.43(18)
N2 C7 C2 C3 178.75(10)
C6 C7 C2 N1 179.65(10)
N2 C7 C2 N1 -0.17(12)
C12 C11 C10 C9 174.05(11)
C8 C9 C10 C11 176.53(11)
C12 C13 C14 C15 -179.52(12)
C16 C15 C14 C13 -178.39(12)
C18 C17 C16 C15 -178.41(13)
C14 C15 C16 C17 179.67(12)
N2 C7 C6 C5 -179.26(12)
C2 C7 C6 C5 0.99(18)
N1 C2 C3 C4 179.30(12)
C7 C2 C3 C4 0.70(18)
C7 C6 C5 C4 0.1(2)
C16 C17 C18 C19 179.99(13)
C2 C3 C4 C5 0.4(2)
C6 C5 C4 C3 -0.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658097
