#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/88/2208840.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_2208840
loop_
_publ_author_name
'Xiao-Yan Yang'
'Ying Li'
'Yan Li'
'Xue-Mei Li'
'Shu-Sheng Zhang'
_publ_section_title
;
 1-(1H-Benzimidazol-2-yl)ethanone
;
_journal_coeditor_code           CI2055
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1936
_journal_page_last               o1937
_journal_paper_doi               10.1107/S1600536806013481
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H8 N2 O'
_chemical_formula_moiety         'C9 H8 N2 O'
_chemical_formula_sum            'C9 H8 N2 O'
_chemical_formula_weight         160.17
_chemical_name_systematic
;
1-(1H-Benzimidazol-2-yl)ethanone
;
_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           SHELXL97
_cell_angle_alpha                95.493(4)
_cell_angle_beta                 94.159(4)
_cell_angle_gamma                108.960(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7270(16)
_cell_length_b                   7.102(2)
_cell_length_c                   10.322(3)
_cell_measurement_reflns_used    864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4
_cell_measurement_theta_min      2.6
_cell_volume                     392.83(19)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2230
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0495
_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)+(0.0803P)²+0.1068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                1194
_reflns_number_total             1495
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2055.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        392.81(19)
_cod_database_code               2208840
_cod_database_fobs_code          2208840
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
O O1 0.5617(3) 0.3248(2) 0.11628(14) 0.0601(5) Uani d . 1
N N1 0.2748(3) 0.5778(2) 0.13256(14) 0.0440(4) Uani d . 1
H H1A 0.3266 0.5748 0.0565 0.053 Uiso calc R 1
N N2 0.2149(3) 0.5080(2) 0.33716(15) 0.0431(4) Uani d . 1
C C1 -0.0451(4) 0.7286(3) 0.38080(19) 0.0472(5) Uani d . 1
H H1B -0.0698 0.7013 0.4660 0.057 Uiso calc R 1
C C2 -0.1457(4) 0.8540(3) 0.3242(2) 0.0534(6) Uani d . 1
H H2 -0.2404 0.9134 0.3722 0.064 Uiso calc R 1
C C3 -0.1110(4) 0.8965(3) 0.1962(2) 0.0553(6) Uani d . 1
H H3 -0.1843 0.9823 0.1611 0.066 Uiso calc R 1
C C4 0.0287(4) 0.8146(3) 0.1206(2) 0.0508(5) Uani d . 1
H H4 0.0527 0.8434 0.0356 0.061 Uiso calc R 1
C C5 0.1322(3) 0.6868(3) 0.17810(18) 0.0411(5) Uani d . 1
C C6 0.0972(3) 0.6420(3) 0.30580(18) 0.0403(5) Uani d . 1
C C7 0.3180(3) 0.4756(3) 0.23110(17) 0.0414(5) Uani d . 1
C C8 0.4727(4) 0.3449(3) 0.21827(19) 0.0453(5) Uani d . 1
C C9 0.5127(4) 0.2435(3) 0.3333(2) 0.0537(6) Uani d . 1
H H9A 0.6569 0.2041 0.3262 0.081 Uiso calc R 1
H H9B 0.3701 0.1268 0.3357 0.081 Uiso calc R 1
H H9C 0.5368 0.3342 0.4121 0.081 Uiso calc R 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 0.0741(10) 0.0756(11) 0.0467(9) 0.0411(9) 0.0242(7) 0.0153(7)
N1 0.0518(9) 0.0562(10) 0.0308(8) 0.0237(8) 0.0130(7) 0.0114(7)
N2 0.0474(9) 0.0503(10) 0.0372(9) 0.0208(8) 0.0115(7) 0.0120(7)
C1 0.0564(12) 0.0532(12) 0.0389(10) 0.0240(10) 0.0155(9) 0.0113(8)
C2 0.0600(13) 0.0567(13) 0.0538(12) 0.0298(11) 0.0170(10) 0.0118(10)
C3 0.0637(13) 0.0575(13) 0.0569(13) 0.0329(11) 0.0106(10) 0.0186(10)
C4 0.0600(12) 0.0581(13) 0.0413(11) 0.0246(10) 0.0109(9) 0.0190(9)
C5 0.0433(10) 0.0452(11) 0.0368(10) 0.0158(8) 0.0083(8) 0.0090(8)
C6 0.0429(10) 0.0438(11) 0.0361(10) 0.0150(9) 0.0079(7) 0.0095(8)
C7 0.0450(10) 0.0476(11) 0.0355(10) 0.0184(9) 0.0085(8) 0.0103(8)
C8 0.0481(10) 0.0504(12) 0.0406(11) 0.0191(9) 0.0106(8) 0.0079(8)
C9 0.0634(13) 0.0594(13) 0.0500(12) 0.0325(11) 0.0117(10) 0.0160(10)
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
C7 N1 C5 106.58(15)
C7 N1 H1A 126.7
C5 N1 H1A 126.7
C7 N2 C6 104.08(15)
C2 C1 C6 117.53(18)
C2 C1 H1B 121.2
C6 C1 H1B 121.2
C1 C2 C3 122.0(2)
C1 C2 H2 119.0
C3 C2 H2 119.0
C4 C3 C2 121.7(2)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 116.45(18)
C3 C4 H4 121.8
C5 C4 H4 121.8
N1 C5 C4 132.42(17)
N1 C5 C6 105.24(16)
C4 C5 C6 122.33(18)
N2 C6 C5 110.35(17)
N2 C6 C1 129.70(17)
C5 C6 C1 119.94(18)
N2 C7 N1 113.75(17)
N2 C7 C8 124.41(17)
N1 C7 C8 121.82(16)
O1 C8 C7 119.74(18)
O1 C8 C9 122.88(19)
C7 C8 C9 117.38(17)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C8 1.218(2) yes
N1 C7 1.358(2) yes
N1 C5 1.373(2) yes
N1 H1A 0.86 ?
N2 C7 1.317(2) yes
N2 C6 1.382(3) yes
C1 C2 1.360(3) ?
C1 C6 1.403(3) ?
C1 H1B 0.93 ?
C2 C3 1.397(3) ?
C2 H2 0.93 ?
C3 C4 1.376(3) ?
C3 H3 0.93 ?
C4 C5 1.389(3) ?
C4 H4 0.93 ?
C5 C6 1.399(3) ?
C7 C8 1.481(3) ?
C8 C9 1.487(3) ?
C9 H9A 0.96 ?
C9 H9B 0.96 ?
C9 H9C 0.96 ?
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
_geom_hbond_publ_flag
N1 H1A O1 2_665 0.86 2.05 2.868(2) 158 yes
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
C6 C1 C2 C3 0.1(3)
C1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 0.4(3)
C7 N1 C5 C4 -178.6(2)
C7 N1 C5 C6 0.0(2)
C3 C4 C5 N1 178.6(2)
C3 C4 C5 C6 0.1(3)
C7 N2 C6 C5 0.4(2)
C7 N2 C6 C1 179.33(19)
N1 C5 C6 N2 -0.3(2)
C4 C5 C6 N2 178.55(18)
N1 C5 C6 C1 -179.32(17)
C4 C5 C6 C1 -0.5(3)
C2 C1 C6 N2 -178.51(19)
C2 C1 C6 C5 0.4(3)
C6 N2 C7 N1 -0.4(2)
C6 N2 C7 C8 178.18(18)
C5 N1 C7 N2 0.2(2)
C5 N1 C7 C8 -178.37(17)
N2 C7 C8 O1 -179.57(18)
N1 C7 C8 O1 -1.1(3)
N2 C7 C8 C9 0.2(3)
N1 C7 C8 C9 178.64(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 63505
