#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/71/2237147.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_2237147
loop_
_publ_author_name
'Ouzidan, Younès'
'Kandri Rodi, Youssef'
'Ouazzani Chahdi, Fouad'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 1-(Prop-2-ynyl)-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           GK2546
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o119
_journal_paper_doi               10.1107/S160053681205088X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H8 N2 O'
_chemical_formula_moiety         'C10 H8 N2 O'
_chemical_formula_sum            'C10 H8 N2 O'
_chemical_formula_weight         172.18
_chemical_melting_point          399
_chemical_name_systematic
;
1-(Prop-2-ynyl)-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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.645(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5553(6)
_cell_length_b                   18.001(3)
_cell_length_c                   10.7488(13)
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.95
_cell_volume                     879.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_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 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10826
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.164
_refine_ls_extinction_coef       0.018(4)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0351
_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)+(0.0493P)²+0.1197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                1753
_reflns_number_total             2080
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2546.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237147
_cod_database_fobs_code          2237147
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_symmetry_multiplicity
O O1 0.43254(19) 0.40104(4) 0.43888(7) 0.0527(2) Uani d . 1 1
N N1 0.25564(19) 0.46700(5) 0.60486(8) 0.0425(2) Uani d . 1 1
H H1 0.3557 0.5125 0.5955 0.051 Uiso d R 1 1
N N2 0.0986(2) 0.35310(5) 0.57304(8) 0.0436(2) Uani d . 1 1
C C1 0.2795(2) 0.40708(5) 0.52935(9) 0.0412(2) Uani d . 1 1
C C2 0.0662(2) 0.45135(6) 0.69742(9) 0.0412(2) Uani d . 1 1
C C3 -0.0238(3) 0.49315(7) 0.79538(11) 0.0523(3) Uani d . 1 1
H H3 0.0420 0.5416 0.8087 0.063 Uiso calc R 1 1
C C4 -0.2163(3) 0.46000(9) 0.87330(12) 0.0623(4) Uani d . 1 1
H H4 -0.2806 0.4868 0.9403 0.075 Uiso calc R 1 1
C C5 -0.3150(3) 0.38814(9) 0.85397(12) 0.0625(4) Uani d . 1 1
H H5 -0.4446 0.3677 0.9080 0.075 Uiso calc R 1 1
C C6 -0.2248(3) 0.34587(7) 0.75573(11) 0.0543(3) Uani d . 1 1
H H6 -0.2904 0.2974 0.7427 0.065 Uiso calc R 1 1
C C7 -0.0329(2) 0.37902(6) 0.67788(9) 0.0421(3) Uani d . 1 1
C C8 0.0605(3) 0.27990(6) 0.51808(11) 0.0539(3) Uani d . 1 1
H H8A 0.1497 0.2789 0.4385 0.065 Uiso calc R 1 1
H H8B -0.1478 0.2697 0.5029 0.065 Uiso calc R 1 1
C C9 0.1941(3) 0.22211(6) 0.59936(12) 0.0553(3) Uani d . 1 1
C C10 0.2989(4) 0.17785(7) 0.66881(15) 0.0737(4) Uani d . 1 1
H H10 0.3795 0.1424 0.7281 0.088 Uiso d R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0709(5) 0.0453(4) 0.0429(4) -0.0091(4) 0.0121(4) -0.0023(3)
N1 0.0500(5) 0.0341(4) 0.0435(5) -0.0036(3) 0.0030(4) 0.0009(3)
N2 0.0516(5) 0.0355(4) 0.0434(5) -0.0065(4) 0.0002(4) 0.0010(3)
C1 0.0490(6) 0.0359(5) 0.0381(5) -0.0023(4) -0.0020(4) 0.0038(4)
C2 0.0389(5) 0.0424(5) 0.0415(5) 0.0029(4) -0.0029(4) 0.0030(4)
C3 0.0491(6) 0.0549(7) 0.0525(6) 0.0059(5) 0.0004(5) -0.0075(5)
C4 0.0502(7) 0.0862(10) 0.0506(7) 0.0099(6) 0.0061(5) -0.0070(6)
C5 0.0464(6) 0.0881(10) 0.0536(7) -0.0025(6) 0.0081(5) 0.0120(6)
C6 0.0478(6) 0.0594(7) 0.0555(7) -0.0086(5) 0.0009(5) 0.0114(5)
C7 0.0401(5) 0.0444(6) 0.0411(5) -0.0010(4) -0.0038(4) 0.0049(4)
C8 0.0690(8) 0.0412(6) 0.0505(6) -0.0135(5) -0.0032(5) -0.0032(5)
C9 0.0709(8) 0.0365(6) 0.0590(7) -0.0124(5) 0.0083(6) -0.0038(5)
C10 0.0977(11) 0.0425(7) 0.0799(10) -0.0040(7) -0.0020(8) 0.0087(6)
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 N1 C2 110.15(9)
C1 N1 H1 124.5
C2 N1 H1 125.3
C1 N2 C7 109.75(9)
C1 N2 C8 124.15(9)
C7 N2 C8 126.08(9)
C3 C2 N1 131.78(10)
C3 C2 C7 121.20(10)
N1 C2 C7 107.02(9)
C6 C7 C2 121.62(10)
C6 C7 N2 131.84(10)
C2 C7 N2 106.54(9)
O1 C1 N1 127.61(9)
O1 C1 N2 125.87(9)
N1 C1 N2 106.52(9)
N2 C8 C9 111.58(9)
N2 C8 H8A 109.3
C9 C8 H8A 109.3
N2 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 108.0
C10 C9 C8 177.04(14)
C2 C3 C4 117.20(12)
C2 C3 H3 121.4
C4 C3 H3 121.4
C7 C6 C5 116.98(12)
C7 C6 H6 121.5
C5 C6 H6 121.5
C4 C5 C6 121.32(12)
C4 C5 H5 119.3
C6 C5 H5 119.3
C5 C4 C3 121.67(12)
C5 C4 H4 119.2
C3 C4 H4 119.2
C9 C10 H10 177.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3583(13)
N1 C2 1.3869(13)
N1 H1 0.9458
N2 C1 1.3760(13)
N2 C7 1.3900(14)
N2 C8 1.4500(13)
C2 C3 1.3775(15)
C2 C7 1.3894(15)
O1 C1 1.2367(13)
C7 C6 1.3835(15)
C8 C9 1.4657(17)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.1725(19)
C3 C4 1.3856(18)
C3 H3 0.9300
C6 C5 1.3848(19)
C6 H6 0.9300
C5 C4 1.381(2)
C5 H5 0.9300
C4 H4 0.9300
C10 H10 0.9580
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 3_666 0.95 1.88 2.8226(12) 174
C10 H10 O1 4_566 0.96 2.39 3.2541(17) 149
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 N1 C2 C3 178.95(11)
C1 N1 C2 C7 -0.44(11)
C3 C2 C7 C6 -0.13(16)
N1 C2 C7 C6 179.33(9)
C3 C2 C7 N2 -179.88(9)
N1 C2 C7 N2 -0.42(11)
C1 N2 C7 C6 -178.59(11)
C8 N2 C7 C6 -0.07(18)
C1 N2 C7 C2 1.13(11)
C8 N2 C7 C2 179.65(10)
C2 N1 C1 O1 -178.79(10)
C2 N1 C1 N2 1.12(11)
C7 N2 C1 O1 178.52(10)
C8 N2 C1 O1 -0.04(17)
C7 N2 C1 N1 -1.39(11)
C8 N2 C1 N1 -179.94(9)
C1 N2 C8 C9 109.99(12)
C7 N2 C8 C9 -68.32(15)
N1 C2 C3 C4 -179.25(10)
C7 C2 C3 C4 0.07(16)
C2 C7 C6 C5 0.22(16)
N2 C7 C6 C5 179.90(11)
C7 C6 C5 C4 -0.25(18)
C6 C5 C4 C3 0.2(2)
C2 C3 C4 C5 -0.10(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23977781
