#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/22/2222268.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_2222268
loop_
_publ_author_name
'Özel Güven, Özden'
'Erdoğan, Taner'
'Coles, Simon J.'
'Hökelek, Tuncer'
_publ_section_title
;
 2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone
 O-propyloxime
;
_journal_coeditor_code           CI2817
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1517
_journal_page_last               o1518
_journal_paper_doi               10.1107/S1600536809020844
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H17 N3 O2'
_chemical_formula_moiety         'C16 H17 N3 O2'
_chemical_formula_sum            'C16 H17 N3 O2'
_chemical_formula_weight         283.33
_chemical_name_systematic
;
2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.3540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4164(2)
_cell_length_b                   18.2524(3)
_cell_length_c                   10.2246(2)
_cell_measurement_reflns_used    3395
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1462.87(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker--Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'φ & 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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19714
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.356
_refine_ls_extinction_coef       0.065(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0431
_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)+(0.0594P)²+0.2758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                2755
_reflns_number_total             3344
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2817.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222268
_cod_database_fobs_code          2222268
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_disorder_assembly
_atom_site_disorder_group
O O1 0.43354(11) 0.47469(5) 0.69234(9) 0.0210(2) Uani d . 1 . .
O O2 0.62124(10) 0.35487(5) 0.44862(9) 0.0215(2) Uani d . 1 . .
N N1 0.81649(13) 0.45397(6) 0.87655(10) 0.0191(2) Uani d . 1 . .
N N2 0.81640(14) 0.44200(6) 1.09515(11) 0.0234(3) Uani d . 1 . .
N N3 0.73483(13) 0.39962(6) 0.55091(11) 0.0203(2) Uani d . 1 . .
C C1 0.75737(16) 0.47823(7) 0.97642(13) 0.0226(3) Uani d . 1 . .
H H1 0.680(2) 0.5192(8) 0.9590(16) 0.025(4) Uiso d . 1 . .
C C2 0.92279(15) 0.38916(7) 1.07227(12) 0.0196(3) Uani d . 1 . .
C C3 1.01939(16) 0.33471(7) 1.16205(13) 0.0229(3) Uani d . 1 . .
H H3 1.016(2) 0.3284(9) 1.2569(17) 0.034(4) Uiso d . 1 . .
C C4 1.11688(16) 0.28954(7) 1.11299(14) 0.0250(3) Uani d . 1 . .
H H4 1.185(2) 0.2500(9) 1.1699(17) 0.035(4) Uiso d . 1 . .
C C5 1.11963(16) 0.29780(7) 0.97705(14) 0.0249(3) Uani d . 1 . .
H H5 1.192(2) 0.2655(9) 0.9461(16) 0.033(4) Uiso d . 1 . .
C C6 1.02292(16) 0.35075(7) 0.88540(13) 0.0223(3) Uani d . 1 . .
H H6 1.0243(19) 0.3573(8) 0.7909(16) 0.026(4) Uiso d . 1 . .
C C7 0.92492(15) 0.39601(6) 0.93600(12) 0.0180(3) Uani d . 1 . .
C C8 0.77611(17) 0.48381(7) 0.73516(13) 0.0209(3) Uani d . 1 . .
H H81 0.8843(18) 0.4894(8) 0.7176(14) 0.018(3) Uiso d . 1 . .
H H82 0.7235(19) 0.5324(8) 0.7319(15) 0.021(4) Uiso d . 1 . .
C C9 0.65977(15) 0.43432(6) 0.62241(12) 0.0177(3) Uani d . 1 . .
C C10 0.48021(15) 0.42984(6) 0.60389(12) 0.0176(3) Uani d . 1 . .
C C11 0.34138(16) 0.39130(7) 0.52080(13) 0.0195(3) Uani d . 1 . .
H H11 0.3406(18) 0.3571(8) 0.4478(15) 0.024(4) Uiso d . 1 . .
C C12 0.20149(17) 0.41338(7) 0.55880(14) 0.0228(3) Uani d . 1 . .
H H12 0.081(2) 0.3957(8) 0.5195(16) 0.027(4) Uiso d . 1 . .
C C13 0.26348(17) 0.46348(7) 0.66207(13) 0.0233(3) Uani d . 1 . .
H H13 0.2152(18) 0.4915(8) 0.7179(15) 0.021(3) Uiso d . 1 . .
C C14 0.71245(17) 0.31673(8) 0.37379(15) 0.0269(3) Uani d . 1 . .
H H141 0.813(2) 0.2925(9) 0.4441(17) 0.032(4) Uiso d . 1 . .
H H142 0.749(2) 0.3531(9) 0.3176(17) 0.034(4) Uiso d . 1 . .
C C15 0.59066(18) 0.26057(8) 0.28123(14) 0.0278(3) Uani d . 1 . .
H H151 0.650(2) 0.2349(10) 0.2257(17) 0.040(4) Uiso d . 1 . .
H H152 0.493(2) 0.2866(9) 0.2113(18) 0.040(5) Uiso d . 1 . .
C C16 0.52829(18) 0.20602(8) 0.36374(15) 0.0287(3) Uani d . 1 . .
H H161 0.624(2) 0.1794(10) 0.4348(19) 0.048(5) Uiso d . 1 . .
H H162 0.468(2) 0.2317(9) 0.4205(16) 0.036(4) Uiso d . 1 . .
H H163 0.449(2) 0.1687(10) 0.3015(19) 0.047(5) Uiso d . 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
C13 O1 C10 . . 106.73(9) ?
N3 O2 C14 . . 109.14(9) ?
C1 N1 C7 . . 106.35(10) ?
C1 N1 C8 . . 127.02(11) ?
C7 N1 C8 . . 126.62(10) ?
C1 N2 C2 . . 104.12(10) ?
C9 N3 O2 . . 111.61(10) ?
N1 C1 H1 . . 121.3(9) ?
N2 C1 N1 . . 114.29(11) ?
N2 C1 H1 . . 124.4(9) ?
N2 C2 C3 . . 129.71(11) ?
N2 C2 C7 . . 110.24(11) ?
C3 C2 C7 . . 120.05(11) ?
C4 C3 C2 . . 117.87(11) ?
C4 C3 H3 . . 121.4(10) ?
C2 C3 H3 . . 120.7(10) ?
C3 C4 C5 . . 121.40(12) ?
C3 C4 H4 . . 121.7(9) ?
C5 C4 H4 . . 116.9(9) ?
C6 C5 C4 . . 121.75(12) ?
C6 C5 H5 . . 118.9(9) ?
C4 C5 H5 . . 119.4(9) ?
C5 C6 C7 . . 116.36(11) ?
C5 C6 H6 . . 122.6(9) ?
C7 C6 H6 . . 121.1(9) ?
N1 C7 C6 . . 132.42(11) ?
N1 C7 C2 . . 105.01(10) ?
C6 C7 C2 . . 122.57(11) ?
N1 C8 C9 . . 112.58(9) ?
N1 C8 H81 . . 108.5(8) ?
C9 C8 H81 . . 107.8(8) ?
N1 C8 H82 . . 108.0(8) ?
C9 C8 H82 . . 110.7(9) ?
H81 C8 H82 . . 109.2(12) ?
N3 C9 C10 . . 126.66(11) ?
N3 C9 C8 . . 114.21(11) ?
C10 C9 C8 . . 119.13(10) ?
C11 C10 O1 . . 109.32(10) ?
C11 C10 C9 . . 136.37(11) ?
O1 C10 C9 . . 114.31(10) ?
C10 C11 C12 . . 106.84(11) ?
C10 C11 H11 . . 125.1(9) ?
C12 C11 H11 . . 128.0(9) ?
C13 C12 C11 . . 106.40(11) ?
C13 C12 H12 . . 125.5(9) ?
C11 C12 H12 . . 128.1(9) ?
C12 C13 O1 . . 110.70(11) ?
C12 C13 H13 . . 134.4(9) ?
O1 C13 H13 . . 114.9(9) ?
O2 C14 C15 . . 106.74(10) ?
O2 C14 H142 . . 108.7(9) ?
C15 C14 H142 . . 111.9(9) ?
O2 C14 H141 . . 108.0(9) ?
C15 C14 H141 . . 110.9(9) ?
H142 C14 H141 . . 110.5(13) ?
C14 C15 C16 . . 112.93(11) ?
C14 C15 H151 . . 107.9(10) ?
C16 C15 H151 . . 110.7(10) ?
C14 C15 H152 . . 108.7(10) ?
C16 C15 H152 . . 110.5(10) ?
H151 C15 H152 . . 105.7(13) ?
C15 C16 H161 . . 112.0(10) ?
C15 C16 H162 . . 111.2(9) ?
H161 C16 H162 . . 104.4(13) ?
C15 C16 H163 . . 112.1(10) ?
H161 C16 H163 . . 107.8(15) ?
H162 C16 H163 . . 108.8(14) ?
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 C10 . 1.3787(14) ?
O1 C13 . 1.3652(16) ?
O2 N3 . 1.3952(13) ?
O2 C14 . 1.4447(15) ?
N1 C1 . 1.3625(16) ?
N1 C7 . 1.3847(15) ?
N1 C8 . 1.4643(15) ?
N2 C1 . 1.3110(17) ?
N2 C2 . 1.3927(16) ?
N3 C9 . 1.2927(16) ?
C1 H1 . 0.963(15) ?
C2 C3 . 1.3956(18) ?
C2 C7 . 1.4055(17) ?
C3 H3 . 0.987(16) ?
C4 C3 . 1.3800(18) ?
C4 C5 . 1.4066(19) ?
C4 H4 . 0.973(17) ?
C5 H5 . 0.982(16) ?
C6 C5 . 1.3854(18) ?
C6 C7 . 1.3933(17) ?
C6 H6 . 0.978(15) ?
C8 H81 . 0.996(14) ?
C8 H82 . 0.987(15) ?
C9 C8 . 1.5105(16) ?
C9 C10 . 1.4553(16) ?
C11 C10 . 1.3635(17) ?
C11 C12 . 1.4257(17) ?
C11 H11 . 0.971(15) ?
C12 H12 . 0.999(16) ?
C13 C12 . 1.3499(19) ?
C13 H13 . 0.959(15) ?
C14 H141 . 0.994(16) ?
C14 H142 . 0.999(17) ?
C15 C14 . 1.5136(19) ?
C15 C16 . 1.517(2) ?
C15 H151 . 0.999(17) ?
C15 H152 . 0.994(18) ?
C16 H161 . 0.993(19) ?
C16 H162 . 1.015(17) ?
C16 H163 . 1.001(19) ?
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
C11 H11 O2 . 0.97(2) 2.359(16) 2.7930(17) 106.0(10) yes
C13 H13 N2 3_667 0.96(2) 2.360(15) 3.2872(17) 162.0(10) yes
C14 H141 Cg1 4_554 0.99(2) 2.968(17) 3.8346(16) 146.0(10) yes
C16 H161 Cg2 4_554 0.99(2) 2.685(18) 3.5644(16) 148.0(10) yes
C16 H163 Cg3 4_554 1.00(2) 2.643(18) 3.5901(15) 157.0(10) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 O1 C10 C11 . . . . -0.29(13) ?
C13 O1 C10 C9 . . . . -179.60(10) ?
C10 O1 C13 C12 . . . . 0.20(13) ?
C14 O2 N3 C9 . . . . -179.10(10) ?
N3 O2 C14 C15 . . . . 171.16(10) ?
C7 N1 C1 N2 . . . . 0.07(15) ?
C8 N1 C1 N2 . . . . -179.00(11) ?
C1 N1 C7 C6 . . . . -179.14(13) ?
C8 N1 C7 C6 . . . . -0.1(2) ?
C1 N1 C7 C2 . . . . 0.18(13) ?
C8 N1 C7 C2 . . . . 179.25(11) ?
C1 N1 C8 C9 . . . . -107.61(14) ?
C7 N1 C8 C9 . . . . 73.51(15) ?
C2 N2 C1 N1 . . . . -0.28(14) ?
C1 N2 C2 C3 . . . . -179.59(13) ?
C1 N2 C2 C7 . . . . 0.39(13) ?
O2 N3 C9 C10 . . . . -0.07(16) ?
O2 N3 C9 C8 . . . . 179.98(9) ?
N2 C2 C3 C4 . . . . -179.13(12) ?
C7 C2 C3 C4 . . . . 0.89(18) ?
N2 C2 C7 N1 . . . . -0.36(13) ?
C3 C2 C7 N1 . . . . 179.63(11) ?
N2 C2 C7 C6 . . . . 179.04(11) ?
C3 C2 C7 C6 . . . . -0.97(18) ?
C5 C4 C3 C2 . . . . 0.06(19) ?
C3 C4 C5 C6 . . . . -1.0(2) ?
C7 C6 C5 C4 . . . . 0.93(18) ?
C5 C6 C7 N1 . . . . 179.26(12) ?
C5 C6 C7 C2 . . . . 0.05(18) ?
N3 C9 C8 N1 . . . . -106.07(12) ?
C10 C9 C8 N1 . . . . 73.98(14) ?
N3 C9 C10 C11 . . . . 2.8(2) ?
C8 C9 C10 C11 . . . . -177.25(13) ?
N3 C9 C10 O1 . . . . -178.13(11) ?
C8 C9 C10 O1 . . . . 1.81(15) ?
C12 C11 C10 O1 . . . . 0.26(13) ?
C12 C11 C10 C9 . . . . 179.35(13) ?
C10 C11 C12 C13 . . . . -0.13(14) ?
O1 C13 C12 C11 . . . . -0.04(14) ?
C16 C15 C14 O2 . . . . -59.43(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742534
