#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/90/2219052.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_2219052
loop_
_publ_author_name
'Özek, Arzu'
'Büyükgüngör, Orhan'
'Albayrak, Çiğdem'
'Odabaşoğlu, Mustafa'
_publ_section_title
;
 X-ray and computational structural study of
 (E)-2-(4-chlorophenyliminomethyl)-4-methoxyphenol
;
_journal_coeditor_code           HK2503
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1613
_journal_page_last               o1614
_journal_paper_doi               10.1107/S1600536808023416
_journal_volume                  64
_journal_year                    2008
_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-chlorophenyliminomethyl)-4-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                 93.361(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.2642(19)
_cell_length_b                   4.7101(3)
_cell_length_c                   12.2175(12)
_cell_measurement_reflns_used    10205
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      1.67
_cell_volume                     1221.56(18)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;WinGX (Farrugia, 1999) and GAUSSIAN
(Frisch et al.,2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       ω
_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  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10205
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9252
_exptl_absorpt_correction_T_min  0.8250
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prismatic long stick'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.437
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0372
_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)+(0.0641P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1789
_reflns_number_total             2364
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2503.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219052
_cod_database_fobs_code          2219052
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
Cl Cl1 0.03208(2) 1.40379(9) 0.66121(4) 0.06631(18) Uani d . 1
O O1 0.26185(6) 0.2746(3) 0.35438(10) 0.0677(4) Uani d . 1
H H1 0.2404(12) 0.393(5) 0.394(2) 0.112(9) Uiso d . 1
O O2 0.42346(6) -0.2199(3) 0.66813(10) 0.0676(4) Uani d . 1
N N1 0.21631(6) 0.5615(3) 0.51562(10) 0.0455(3) Uani d . 1
C C1 0.29911(7) 0.2216(3) 0.54240(12) 0.0428(3) Uani d . 1
C C2 0.30182(7) 0.1541(3) 0.43144(12) 0.0480(4) Uani d . 1
C C3 0.34597(8) -0.0395(4) 0.39932(13) 0.0575(4) Uani d . 1
H H3 0.3478 -0.0841 0.3254 0.069 Uiso calc R 1
C C4 0.38738(8) -0.1674(4) 0.47512(14) 0.0551(4) Uani d . 1
H H4 0.4170 -0.2964 0.4521 0.066 Uiso calc R 1
C C5 0.38493(7) -0.1042(3) 0.58541(13) 0.0493(4) Uani d . 1
C C6 0.34078(7) 0.0873(3) 0.61831(13) 0.0484(3) Uani d . 1
H H6 0.3387 0.1278 0.6925 0.058 Uiso calc R 1
C C7 0.47390(9) -0.3918(4) 0.63688(19) 0.0753(6) Uani d . 1
H H7A 0.5012 -0.2819 0.5936 0.090 Uiso calc R 1
H H7B 0.4576 -0.5499 0.5945 0.090 Uiso calc R 1
H H7C 0.4971 -0.4604 0.7013 0.090 Uiso calc R 1
C C8 0.25442(7) 0.4252(3) 0.58089(12) 0.0461(3) Uani d . 1
H H8 0.2534 0.4579 0.6558 0.055 Uiso calc R 1
C C9 0.17376(7) 0.7637(3) 0.55533(12) 0.0436(3) Uani d . 1
C C10 0.12943(7) 0.8772(3) 0.48017(13) 0.0522(4) Uani d . 1
H H10 0.1291 0.8199 0.4073 0.063 Uiso calc R 1
C C11 0.08576(8) 1.0737(3) 0.51122(14) 0.0550(4) Uani d . 1
H H11 0.0561 1.1474 0.4599 0.066 Uiso calc R 1
C C12 0.08649(7) 1.1592(3) 0.61875(14) 0.0496(4) Uani d . 1
C C13 0.13070(8) 1.0524(4) 0.69489(14) 0.0557(4) Uani d . 1
H H13 0.1312 1.1129 0.7674 0.067 Uiso calc R 1
C C14 0.17395(7) 0.8564(3) 0.66347(13) 0.0531(4) Uani d . 1
H H14 0.2037 0.7848 0.7151 0.064 Uiso calc R 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
C2 O1 H1 102.0(17)
C5 O2 C7 117.19(14)
C8 N1 C9 121.22(13)
C6 C1 C2 118.74(14)
C6 C1 C8 119.18(13)
C2 C1 C8 122.08(13)
O1 C2 C3 119.19(14)
O1 C2 C1 121.27(14)
C3 C2 C1 119.54(14)
C4 C3 C2 121.03(15)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 120.05(15)
C3 C4 H4 120.0
C5 C4 H4 120.0
O2 C5 C6 115.56(14)
O2 C5 C4 125.11(15)
C6 C5 C4 119.33(14)
C5 C6 C1 121.29(14)
C5 C6 H6 119.4
C1 C6 H6 119.4
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C1 122.35(14)
N1 C8 H8 118.8
C1 C8 H8 118.8
C10 C9 C14 118.22(14)
C10 C9 N1 117.10(13)
C14 C9 N1 124.68(13)
C11 C10 C9 121.32(15)
C11 C10 H10 119.3
C9 C10 H10 119.3
C12 C11 C10 119.31(14)
C12 C11 H11 120.3
C10 C11 H11 120.3
C11 C12 C13 120.51(15)
C11 C12 Cl1 120.72(12)
C13 C12 Cl1 118.77(13)
C14 C13 C12 119.87(15)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C9 120.76(14)
C13 C14 H14 119.6
C9 C14 H14 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1 0.88(3)
C1 C6 1.396(2)
C1 C2 1.397(2)
C1 C8 1.448(2)
C2 O1 1.3554(18)
C2 C3 1.382(2)
C3 C4 1.379(2)
C3 H3 0.9300
C4 C5 1.384(2)
C4 H4 0.9300
C5 O2 1.3756(18)
C5 C6 1.379(2)
C6 H6 0.9300
C7 O2 1.414(2)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 N1 1.2763(19)
C8 H8 0.9300
C9 C10 1.384(2)
C9 C14 1.391(2)
C9 N1 1.4186(19)
C10 C11 1.380(2)
C10 H10 0.9300
C11 C12 1.373(2)
C11 H11 0.9300
C12 C13 1.378(2)
C12 Cl1 1.7337(15)
C13 C14 1.374(2)
C13 H13 0.9300
C14 H14 0.9300
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 . 0.88(3) 1.79(3) 2.6210(18) 157(2)
C7 H7C O2 2_646 0.96 2.56 3.495(2) 163.5
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 178.95(14)
C8 C1 C2 O1 -0.9(2)
C6 C1 C2 C3 -0.9(2)
C8 C1 C2 C3 179.23(14)
O1 C2 C3 C4 -179.82(16)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 O2 179.54(16)
C3 C4 C5 C6 0.0(2)
O2 C5 C6 C1 179.51(14)
C4 C5 C6 C1 -0.9(2)
C2 C1 C6 C5 1.4(2)
C8 C1 C6 C5 -178.79(14)
C6 C1 C8 N1 177.90(14)
C2 C1 C8 N1 -2.3(2)
C14 C9 C10 C11 -1.0(2)
N1 C9 C10 C11 179.50(14)
C9 C10 C11 C12 0.3(2)
C10 C11 C12 C13 0.6(2)
C10 C11 C12 Cl1 -179.55(12)
C11 C12 C13 C14 -0.8(2)
Cl1 C12 C13 C14 179.40(12)
C12 C13 C14 C9 0.0(2)
C10 C9 C14 C13 0.9(2)
N1 C9 C14 C13 -179.70(14)
C1 C8 N1 C9 -178.85(13)
C10 C9 N1 C8 -172.84(13)
C14 C9 N1 C8 7.7(2)
C6 C5 O2 C7 -172.96(15)
C4 C5 O2 C7 7.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655572
