#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/73/2017357.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_2017357
loop_
_publ_author_name
'Koşar, Başak'
'Albayrak, Çigdem'
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (E)-2-[(4-Chlorophenyl)iminomethyl]-5-methoxyphenol and
 (E)-2-[(2-chlorophenyl)iminomethyl]-5-methoxyphenol: X-ray and
 DFT-calculated structures
;
_journal_coeditor_code           SF3113
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o517
_journal_page_last               o520
_journal_paper_doi               10.1107/S0108270109034350
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H12 Cl N O2'
_chemical_formula_moiety         'C14 H12 Cl N O2'
_chemical_formula_sum            'C14 H12 Cl N O2'
_chemical_formula_weight         261.70
_chemical_name_systematic
;
(E)-2-[(2-chlorophenyl)iminomethyl]-5-methoxyphenol
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.428(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.446(3)
_cell_length_b                   7.2259(7)
_cell_length_c                   16.727(2)
_cell_measurement_reflns_used    1405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      1.98
_cell_volume                     2489.3(5)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and enCIFer (Allen et al.,  2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scan'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10001
_diffrn_reflns_theta_full        27.75
_diffrn_reflns_theta_max         27.75
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.9385
_exptl_absorpt_correction_T_min  0.8384
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0377
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                1854
_reflns_number_total             2885
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3113.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017357
_cod_database_fobs_code          2017357
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_disorder_assembly
_atom_site_disorder_group
C C1 0.42395(8) -0.2233(2) 0.11846(11) 0.0527(4) Uani d . 1 . .
C C2 0.44456(10) -0.4022(2) 0.14697(13) 0.0648(5) Uani d . 1 . .
C C3 0.40265(11) -0.5267(3) 0.16034(14) 0.0750(6) Uani d . 1 . .
C C4 0.33993(12) -0.4775(3) 0.14362(14) 0.0759(6) Uani d . 1 . .
C C5 0.31725(10) -0.3051(3) 0.11152(13) 0.0665(5) Uani d . 1 . .
C C6 0.35919(8) -0.1802(2) 0.09859(12) 0.0565(4) Uani d . 1 . .
C C7 0.52583(9) -0.0879(2) 0.15313(12) 0.0562(4) Uani d . 1 . .
C C8 0.56799(7) 0.0562(2) 0.14682(10) 0.0502(4) Uani d . 1 . .
C C9 0.54375(7) 0.2107(2) 0.09273(10) 0.0486(4) Uani d . 1 . .
C C10 0.58516(7) 0.3512(2) 0.08971(11) 0.0501(4) Uani d . 1 . .
C C11 0.65098(7) 0.3360(2) 0.13993(11) 0.0508(4) Uani d . 1 . .
C C12 0.67613(8) 0.1835(2) 0.19309(12) 0.0579(4) Uani d . 1 . .
C C13 0.63524(8) 0.0480(2) 0.19656(12) 0.0581(4) Uani d . 1 . .
C C14 0.67348(10) 0.6226(3) 0.08690(16) 0.0701(5) Uani d . 1 . .
Cl Cl1 0.33013(2) 0.03715(7) 0.05831(4) 0.0800(2) Uani d . 1 . .
N N1 0.46449(6) -0.08415(17) 0.10849(9) 0.0550(3) Uani d . 1 . .
O O1 0.48004(5) 0.22914(17) 0.04290(9) 0.0624(3) Uani d . 1 . .
O O2 0.69536(5) 0.46541(16) 0.14193(8) 0.0657(3) Uani d . 1 . .
H H1 0.4612(12) 0.132(3) 0.0508(16) 0.098(8) Uiso d . 1 . .
H H2 0.4878(9) -0.440(2) 0.1559(12) 0.065(5) Uiso d . 1 . .
H H3 0.4211(10) -0.645(3) 0.1778(14) 0.083(6) Uiso d . 1 . .
H H4 0.3104(10) -0.555(3) 0.1530(14) 0.084(6) Uiso d . 1 . .
H H5 0.2739(9) -0.264(2) 0.0993(12) 0.065(5) Uiso d . 1 . .
H H7 0.5468(9) -0.180(3) 0.1964(14) 0.075(6) Uiso d . 1 . .
H H10 0.5676(8) 0.450(2) 0.0544(12) 0.060(5) Uiso d . 1 . .
H H12 0.7217(9) 0.176(2) 0.2244(12) 0.066(5) Uiso d . 1 . .
H H13 0.6525(8) -0.058(2) 0.2338(12) 0.066(5) Uiso d . 1 . .
H H14A 0.7106(10) 0.694(3) 0.0989(13) 0.078(6) Uiso d . 1 . .
H H14B 0.6502(10) 0.585(3) 0.0235(16) 0.082(6) Uiso d . 1 . .
H H14C 0.6424(11) 0.686(3) 0.1015(14) 0.085(7) 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 . . 117.60(15) ?
C6 C1 N1 . . 118.31(14) ?
C2 C1 N1 . . 124.10(16) ?
C3 C2 C1 . . 120.3(2) ?
C3 C2 H2 . . 120.1(11) ?
C1 C2 H2 . . 119.5(11) ?
C4 C3 C2 . . 120.6(2) ?
C4 C3 H3 . . 126.0(12) ?
C2 C3 H3 . . 113.3(12) ?
C3 C4 C5 . . 120.47(18) ?
C3 C4 H4 . . 123.9(13) ?
C5 C4 H4 . . 115.7(13) ?
C4 C5 C6 . . 118.99(19) ?
C4 C5 H5 . . 123.5(10) ?
C6 C5 H5 . . 117.4(11) ?
C5 C6 C1 . . 121.89(17) ?
C5 C6 Cl1 . . 118.61(14) ?
C1 C6 Cl1 . . 119.49(12) ?
N1 C7 C8 . . 121.89(16) ?
N1 C7 H7 . . 123.1(11) ?
C8 C7 H7 . . 114.8(11) ?
C9 C8 C13 . . 117.72(14) ?
C9 C8 C7 . . 121.69(14) ?
C13 C8 C7 . . 120.58(15) ?
O1 C9 C10 . . 117.80(14) ?
O1 C9 C8 . . 121.50(13) ?
C10 C9 C8 . . 120.70(14) ?
C11 C10 C9 . . 119.21(15) ?
C11 C10 H10 . . 122.7(11) ?
C9 C10 H10 . . 118.1(11) ?
O2 C11 C10 . . 123.83(14) ?
O2 C11 C12 . . 115.09(13) ?
C10 C11 C12 . . 121.08(14) ?
C13 C12 C11 . . 119.35(15) ?
C13 C12 H12 . . 122.4(11) ?
C11 C12 H12 . . 118.2(11) ?
C12 C13 C8 . . 121.94(16) ?
C12 C13 H13 . . 119.6(10) ?
C8 C13 H13 . . 118.4(10) ?
O2 C14 H14A . . 104.8(12) ?
O2 C14 H14B . . 111.6(11) ?
H14A C14 H14B . . 114.5(17) ?
O2 C14 H14C . . 108.7(13) ?
H14A C14 H14C . . 111.4(17) ?
H14B C14 H14C . . 105.8(17) ?
C7 N1 C1 . . 120.76(15) ?
C9 O1 H1 . . 107.0(16) ?
C11 O2 C14 . . 118.26(13) ?
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
C1 C6 . 1.391(2) ?
C1 C2 . 1.392(2) ?
C1 N1 . 1.4097(19) ?
C2 C3 . 1.383(3) ?
C2 H2 . 0.961(18) ?
C3 C4 . 1.369(3) ?
C3 H3 . 0.94(2) ?
C4 C5 . 1.372(3) ?
C4 H4 . 0.92(2) ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.959(17) ?
C6 Cl1 . 1.7309(18) ?
C7 N1 . 1.279(2) ?
C7 C8 . 1.439(2) ?
C7 H7 . 0.96(2) ?
C8 C9 . 1.403(2) ?
C8 C13 . 1.405(2) ?
C9 O1 . 1.3451(18) ?
C9 C10 . 1.391(2) ?
C10 C11 . 1.383(2) ?
C10 H10 . 0.908(18) ?
C11 O2 . 1.3567(18) ?
C11 C12 . 1.388(2) ?
C12 C13 . 1.359(2) ?
C12 H12 . 0.947(18) ?
C13 H13 . 0.966(18) ?
C14 O2 . 1.421(2) ?
C14 H14A . 0.93(2) ?
C14 H14B . 1.01(2) ?
C14 H14C . 0.94(2) ?
O1 H1 . 0.85(2) ?
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 . 0.85(2) 1.82(2) 2.5991(18) 150(2)
C7 H7 Cg(1) 2_655 0.96(2) 2.98(2) 3.893(2) 160.2(17)
C14 H14b Cg(1) 3_655 1.01(2) 2.91(2) 3.864(3) 156.9(17)
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
C6 C1 C2 C3 . . . . -4.3(3) ?
N1 C1 C2 C3 . . . . 175.78(17) ?
C1 C2 C3 C4 . . . . 1.7(3) ?
C2 C3 C4 C5 . . . . 1.4(3) ?
C3 C4 C5 C6 . . . . -1.8(3) ?
C4 C5 C6 C1 . . . . -1.0(3) ?
C4 C5 C6 Cl1 . . . . -179.85(16) ?
C2 C1 C6 C5 . . . . 4.0(3) ?
N1 C1 C6 C5 . . . . -176.07(17) ?
C2 C1 C6 Cl1 . . . . -177.18(14) ?
N1 C1 C6 Cl1 . . . . 2.7(2) ?
N1 C7 C8 C9 . . . . 1.4(3) ?
N1 C7 C8 C13 . . . . -179.85(17) ?
C13 C8 C9 O1 . . . . 179.88(16) ?
C7 C8 C9 O1 . . . . -1.4(2) ?
C13 C8 C9 C10 . . . . -0.7(2) ?
C7 C8 C9 C10 . . . . 177.98(15) ?
O1 C9 C10 C11 . . . . -179.74(15) ?
C8 C9 C10 C11 . . . . 0.9(2) ?
C9 C10 C11 O2 . . . . -179.74(15) ?
C9 C10 C11 C12 . . . . -0.1(2) ?
O2 C11 C12 C13 . . . . 178.88(16) ?
C10 C11 C12 C13 . . . . -0.8(3) ?
C11 C12 C13 C8 . . . . 0.9(3) ?
C9 C8 C13 C12 . . . . -0.2(3) ?
C7 C8 C13 C12 . . . . -178.91(17) ?
C8 C7 N1 C1 . . . . -177.44(15) ?
C6 C1 N1 C7 . . . . 154.24(16) ?
C2 C1 N1 C7 . . . . -25.8(2) ?
C10 C11 O2 C14 . . . . -2.4(3) ?
C12 C11 O2 C14 . . . . 177.88(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654192
