#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/73/2017356.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_2017356
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-[(4-Chlorophenyl)iminomethyl]-5-methoxyphenol
;
_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                 93.880(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5859(6)
_cell_length_b                   8.9617(6)
_cell_length_c                   25.333(3)
_cell_measurement_reflns_used    1034
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      1.61
_cell_volume                     1265.2(2)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10988
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.8643
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0697
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1505
_reflns_number_total             2440
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3113.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017356
_cod_database_fobs_code          2017356
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
C C1 0.8979(3) 0.5450(2) 0.19344(7) 0.0630(5) Uani d . 1 . .
C C2 1.1110(4) 0.4659(2) 0.19480(8) 0.0736(5) Uani d . 1 . .
H H2 1.1708 0.4226 0.2264 0.088 Uiso calc R 1 . .
C C3 1.2356(4) 0.4505(2) 0.14998(8) 0.0756(5) Uani d . 1 . .
H H3 1.3785 0.3969 0.1513 0.091 Uiso calc R 1 . .
C C4 1.1475(4) 0.5146(2) 0.10348(8) 0.0696(5) Uani d . 1 . .
C C5 0.9382(4) 0.5941(2) 0.10109(8) 0.0782(5) Uani d . 1 . .
H H5 0.8785 0.6366 0.0694 0.094 Uiso calc R 1 . .
C C6 0.8172(3) 0.6103(2) 0.14625(8) 0.0746(5) Uani d . 1 . .
H H6 0.6773 0.6669 0.1449 0.090 Uiso calc R 1 . .
C C7 0.7795(3) 0.4844(2) 0.27826(8) 0.0680(5) Uani d . 1 . .
H H7 0.8951 0.4096 0.2800 0.082 Uiso calc R 1 . .
C C8 0.6311(3) 0.50368(18) 0.32191(7) 0.0619(4) Uani d . 1 . .
C C9 0.4484(3) 0.61090(19) 0.32117(6) 0.0618(4) Uani d . 1 . .
C C10 0.3072(3) 0.6283(2) 0.36363(7) 0.0671(5) Uani d . 1 . .
H H10 0.1864 0.6999 0.3625 0.081 Uiso calc R 1 . .
C C11 0.3473(4) 0.5386(2) 0.40754(7) 0.0678(5) Uani d . 1 . .
C C12 0.5264(4) 0.4304(2) 0.40925(8) 0.0799(6) Uani d . 1 . .
H H12 0.5525 0.3697 0.4388 0.096 Uiso calc R 1 . .
C C13 0.6627(4) 0.4147(2) 0.36714(8) 0.0774(5) Uani d . 1 . .
H H13 0.7815 0.3418 0.3685 0.093 Uiso calc R 1 . .
C C14 0.0517(4) 0.6660(2) 0.45455(8) 0.0924(7) Uani d . 1 . .
H H14A -0.0662 0.6603 0.4252 0.111 Uiso calc R 1 . .
H H14B 0.1346 0.7597 0.4536 0.111 Uiso calc R 1 . .
H H14C -0.0261 0.6582 0.4871 0.111 Uiso calc R 1 . .
N N1 0.7574(3) 0.56732(17) 0.23696(6) 0.0663(4) Uani d . 1 . .
O O1 0.4055(3) 0.70146(15) 0.27921(5) 0.0807(4) Uani d D 1 . .
H H1 0.507(4) 0.675(3) 0.2574(8) 0.115(9) Uiso d D 1 . .
O O2 0.2195(3) 0.54679(16) 0.45124(5) 0.0881(4) Uani d . 1 . .
Cl Cl1 1.30643(11) 0.49517(7) 0.04711(2) 0.0971(2) Uani 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'
Cl Cl 0.1484 0.1585 '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 . . 117.99(17) ?
C6 C1 N1 . . 116.80(17) ?
C2 C1 N1 . . 125.19(18) ?
C3 C2 C1 . . 120.82(19) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 119.57(19) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C5 C4 C3 . . 120.82(18) ?
C5 C4 Cl1 . . 119.88(16) ?
C3 C4 Cl1 . . 119.30(16) ?
C4 C5 C6 . . 119.05(19) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 121.71(18) ?
C5 C6 H6 . . 119.1 ?
C1 C6 H6 . . 119.1 ?
N1 C7 C8 . . 122.02(18) ?
N1 C7 H7 . . 119.0 ?
C8 C7 H7 . . 119.0 ?
C13 C8 C9 . . 116.99(16) ?
C13 C8 C7 . . 121.01(17) ?
C9 C8 C7 . . 122.00(16) ?
O1 C9 C10 . . 117.73(16) ?
O1 C9 C8 . . 120.97(15) ?
C10 C9 C8 . . 121.30(16) ?
C11 C10 C9 . . 119.41(17) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
O2 C11 C10 . . 124.09(17) ?
O2 C11 C12 . . 115.35(17) ?
C10 C11 C12 . . 120.57(17) ?
C13 C12 C11 . . 119.18(18) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C8 . . 122.53(18) ?
C12 C13 H13 . . 118.7 ?
C8 C13 H13 . . 118.7 ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C7 N1 C1 . . 121.88(17) ?
C9 O1 H1 . . 104.9(17) ?
C11 O2 C14 . . 118.11(15) ?
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 . 1.379(3) ?
C1 C2 . 1.384(3) ?
C1 N1 . 1.410(2) ?
C2 C3 . 1.379(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.367(3) ?
C4 Cl1 . 1.7404(19) ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.282(2) ?
C7 C8 . 1.436(2) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.398(3) ?
C8 C9 . 1.401(2) ?
C9 O1 . 1.346(2) ?
C9 C10 . 1.385(2) ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.9300 ?
C11 O2 . 1.359(2) ?
C11 C12 . 1.392(3) ?
C12 C13 . 1.359(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 O2 . 1.428(2) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
O1 H1 . 0.851(16) ?
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 . 0.851(16) 1.806(18) 2.596(2) 154(2)
C13 H13 Cg1 2_745 0.930 3.04 3.896(2) 154.32
C14 H14a Cg2 1_455 0.960 3.10 3.975(2) 152.80
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 . . . . -1.3(3) ?
N1 C1 C2 C3 . . . . -179.94(18) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
C2 C3 C4 Cl1 . . . . 179.78(15) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
Cl1 C4 C5 C6 . . . . -178.92(15) ?
C4 C5 C6 C1 . . . . -1.9(3) ?
C2 C1 C6 C5 . . . . 2.2(3) ?
N1 C1 C6 C5 . . . . -179.05(17) ?
N1 C7 C8 C13 . . . . -178.25(18) ?
N1 C7 C8 C9 . . . . 2.1(3) ?
C13 C8 C9 O1 . . . . 179.97(17) ?
C7 C8 C9 O1 . . . . -0.4(3) ?
C13 C8 C9 C10 . . . . 0.5(3) ?
C7 C8 C9 C10 . . . . -179.83(17) ?
O1 C9 C10 C11 . . . . -179.37(17) ?
C8 C9 C10 C11 . . . . 0.1(3) ?
C9 C10 C11 O2 . . . . 179.88(18) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
O2 C11 C12 C13 . . . . 179.97(19) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C12 C13 C8 . . . . 0.3(3) ?
C9 C8 C13 C12 . . . . -0.7(3) ?
C7 C8 C13 C12 . . . . 179.63(19) ?
C8 C7 N1 C1 . . . . -177.86(16) ?
C6 C1 N1 C7 . . . . 162.47(17) ?
C2 C1 N1 C7 . . . . -18.9(3) ?
C10 C11 O2 C14 . . . . -7.3(3) ?
C12 C11 O2 C14 . . . . 173.10(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726517
