#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/49/2204993.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_2204993
loop_
_publ_author_name
'Odabas̨oǧlu, Mustafa'
'Albayrak, Çiǧdem'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2-(3-Methoxysalicylideneamino)-1H-benzimidazole
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o425
_journal_page_last               o426
_journal_paper_doi               10.1107/S1600536804033069
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H13 N3 O2'
_chemical_formula_moiety         'C15 H13 N3 O2'
_chemical_formula_sum            'C15 H13 N3 O2'
_chemical_formula_weight         267.28
_chemical_name_systematic
;
2-(3-Methoxysalicylideneamino)-1H-benzimidazole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.755(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5450(9)
_cell_length_b                   8.4858(8)
_cell_length_c                   13.2955(10)
_cell_measurement_reflns_used    17957
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.8
_cell_volume                     1314.56(19)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'φ or ω scans?'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_av_sigmaI/netI    0.046
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23491
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.10
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.88
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.88
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.039
_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)+(0.0435P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.076
_refine_ls_wR_factor_ref         0.087
_reflns_number_gt                1519
_reflns_number_total             2590
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6568.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_cell_volume        1314.56(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204993
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_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_type_symbol
C1 0.21604(14) 0.2061(2) 0.57376(14) 0.0435(4) Uani d . 1 C
C2 0.32810(14) 0.14825(19) 0.60831(13) 0.0423(4) Uani d . 1 C
C3 0.34913(15) -0.0010(2) 0.57639(14) 0.0448(4) Uani d . 1 C
C4 0.25974(16) -0.0890(2) 0.50725(15) 0.0540(5) Uani d . 1 C
H4 0.2738 -0.1881 0.4851 0.065 Uiso calc R 1 H
C5 0.14907(17) -0.0303(2) 0.47070(16) 0.0601(5) Uani d . 1 C
H5 0.0893 -0.0896 0.4231 0.072 Uiso calc R 1 H
C6 0.12679(15) 0.1140(2) 0.50387(15) 0.0550(5) Uani d . 1 C
H6 0.0518 0.1513 0.4799 0.066 Uiso calc R 1 H
C7 0.19215(14) 0.3582(2) 0.60881(14) 0.0481(4) Uani d . 1 C
H7 0.1164 0.3920 0.5871 0.058 Uiso calc R 1 H
C8 0.24455(14) 0.5906(2) 0.70480(14) 0.0451(4) Uani d . 1 C
C9 0.28225(14) 0.81828(19) 0.78849(14) 0.0431(4) Uani d . 1 C
C10 0.32800(16) 0.9537(2) 0.84677(16) 0.0554(5) Uani d . 1 C
H10 0.4062 0.9753 0.8715 0.066 Uiso calc R 1 H
C11 0.25211(18) 1.0543(2) 0.86612(17) 0.0633(6) Uani d . 1 C
H11 0.2797 1.1463 0.9050 0.076 Uiso calc R 1 H
C12 0.13526(18) 1.0226(2) 0.82937(17) 0.0630(6) Uani d . 1 C
H12 0.0868 1.0933 0.8448 0.076 Uiso calc R 1 H
C13 0.08975(16) 0.8893(2) 0.77081(16) 0.0559(5) Uani d . 1 C
H13 0.0114 0.8689 0.7463 0.067 Uiso calc R 1 H
C14 0.16476(15) 0.7855(2) 0.74927(14) 0.0452(4) Uani d . 1 C
C15 0.49191(19) -0.1851(2) 0.57436(17) 0.0687(6) Uani d . 1 C
H15A 0.5725 -0.2052 0.6102 0.103 Uiso calc R 1 H
H15B 0.4745 -0.1703 0.4983 0.103 Uiso calc R 1 H
H15C 0.4490 -0.2730 0.5848 0.103 Uiso calc R 1 H
N1 0.27272(12) 0.44835(16) 0.66921(12) 0.0478(4) Uani d . 1 N
N2 0.33154(13) 0.69081(17) 0.75866(12) 0.0461(4) Uani d . 1 N
N3 0.14270(12) 0.64128(17) 0.69562(12) 0.0503(4) Uani d . 1 N
O1 0.41963(10) 0.23297(16) 0.67289(11) 0.0546(4) Uani d . 1 O
O2 0.46188(10) -0.04675(15) 0.61838(10) 0.0579(4) Uani d . 1 O
H2 0.4086(18) 0.675(2) 0.7739(16) 0.071(6) Uiso d . 1 H
H1 0.389(2) 0.333(3) 0.683(2) 0.101(8) Uiso d . 1 H
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
_geom_angle_publ_flag
C2 C1 C6 118.87(16) ?
C2 C1 C7 120.86(15) ?
C6 C1 C7 120.27(15) ?
O1 C2 C3 117.61(15) ?
O1 C2 C1 122.32(15) ?
C3 C2 C1 120.07(15) ?
O2 C3 C4 125.48(16) ?
O2 C3 C2 114.68(15) ?
C4 C3 C2 119.84(16) ?
C3 C4 C5 120.17(17) ?
C3 C4 H4 119.9 ?
C5 C4 H4 119.9 ?
C6 C5 C4 120.58(17) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C5 C6 C1 120.42(17) ?
C5 C6 H6 119.8 ?
C1 C6 H6 119.8 ?
N1 C7 C1 121.73(15) yes
N1 C7 H7 119.1 ?
C1 C7 H7 119.1 ?
N3 C8 N2 114.09(15) yes
N3 C8 N1 128.03(15) yes
N2 C8 N1 117.86(15) yes
N2 C9 C10 132.54(16) ?
N2 C9 C14 105.10(15) ?
C10 C9 C14 122.33(16) ?
C11 C10 C9 116.63(17) ?
C11 C10 H10 121.7 ?
C9 C10 H10 121.7 ?
C10 C11 C12 121.93(18) ?
C10 C11 H11 119.0 ?
C12 C11 H11 119.0 ?
C13 C12 C11 121.48(19) ?
C13 C12 H12 119.3 ?
C11 C12 H12 119.3 ?
C12 C13 C14 117.85(18) ?
C12 C13 H13 121.1 ?
C14 C13 H13 121.1 ?
N3 C14 C13 129.79(16) ?
N3 C14 C9 110.39(15) ?
C13 C14 C9 119.76(16) ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C7 N1 C8 119.33(14) yes
C8 N2 C9 106.57(14) yes
C8 N2 H2 126.5(13) ?
C9 N2 H2 126.9(13) ?
C8 N3 C14 103.84(14) yes
C2 O1 H1 105.3(14) ?
C3 O2 C15 117.19(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.396(2) ?
C1 C6 1.399(2) ?
C1 C7 1.441(2) ?
C2 O1 1.3571(19) yes
C2 C3 1.391(2) ?
C3 O2 1.370(2) yes
C3 C4 1.377(2) ?
C4 C5 1.383(3) ?
C4 H4 0.9300 ?
C5 C6 1.365(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 N1 1.285(2) yes
C7 H7 0.9300 ?
C8 N3 1.310(2) yes
C8 N2 1.359(2) yes
C8 N1 1.389(2) yes
C9 N2 1.375(2) yes
C9 C10 1.386(2) ?
C9 C14 1.397(2) ?
C10 C11 1.372(3) ?
C10 H10 0.9300 ?
C11 C12 1.389(3) ?
C11 H11 0.9300 ?
C12 C13 1.372(3) ?
C12 H12 0.9300 ?
C13 C14 1.394(2) ?
C13 H13 0.9300 ?
C14 N3 1.391(2) yes
C15 O2 1.423(2) yes
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
N2 H2 0.92(2) ?
O1 H1 0.96(3) ?
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
O1 H1 N1 . 0.96(3) 1.71(3) 2.5831(19) 150(2)
C7 H7 N3 . 0.93 2.51 2.832(2) 100
N2 H2 O1 2_656 0.92(2) 2.06(2) 2.9317(19) 156.5(18)
N2 H2 O2 2_656 0.92(2) 2.55(2) 3.211(2) 129.1(16)
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 O1 177.56(17)
C7 C1 C2 O1 -2.2(3)
C6 C1 C2 C3 -2.3(3)
C7 C1 C2 C3 177.98(17)
O1 C2 C3 O2 2.3(2)
C1 C2 C3 O2 -177.88(16)
O1 C2 C3 C4 -177.32(17)
C1 C2 C3 C4 2.5(3)
O2 C3 C4 C5 179.60(19)
C2 C3 C4 C5 -0.9(3)
C3 C4 C5 C6 -1.0(3)
C4 C5 C6 C1 1.3(3)
C2 C1 C6 C5 0.4(3)
C7 C1 C6 C5 -179.87(18)
C2 C1 C7 N1 2.7(3)
C6 C1 C7 N1 -176.98(18)
N2 C9 C10 C11 -176.80(19)
C14 C9 C10 C11 1.1(3)
C9 C10 C11 C12 0.0(3)
C10 C11 C12 C13 -0.6(3)
C11 C12 C13 C14 0.2(3)
C12 C13 C14 N3 177.68(18)
C12 C13 C14 C9 0.9(3)
N2 C9 C14 N3 -0.55(19)
C10 C9 C14 N3 -178.92(17)
N2 C9 C14 C13 176.84(16)
C10 C9 C14 C13 -1.5(3)
C1 C7 N1 C8 -176.99(16)
N3 C8 N1 C7 8.8(3)
N2 C8 N1 C7 -173.05(17)
N3 C8 N2 C9 0.7(2)
N1 C8 N2 C9 -177.71(15)
C10 C9 N2 C8 178.11(19)
C14 C9 N2 C8 -0.03(18)
N2 C8 N3 C14 -1.0(2)
N1 C8 N3 C14 177.21(17)
C13 C14 N3 C8 -176.13(19)
C9 C14 N3 C8 0.9(2)
C4 C3 O2 C15 10.3(3)
C2 C3 O2 C15 -169.29(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173706
