#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/25/2232504.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_2232504
loop_
_publ_author_name
'Ji, Hong-Bo'
'Zhang, Pei-Zhi'
'Wu, Jun'
_publ_section_title
;
 (E)-4-Chloro-2-{[4-(3,5-dichloropyridin-2-yloxy)phenylimino]methyl}phenol
;
_journal_coeditor_code           XU5335
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2984
_journal_paper_doi               10.1107/S1600536811041584
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H11 Cl3 N2 O2'
_chemical_formula_moiety         'C18 H11 Cl3 N2 O2'
_chemical_formula_sum            'C18 H11 Cl3 N2 O2'
_chemical_formula_weight         393.64
_chemical_name_systematic
;
(E)-4-Chloro-2-{[4-(3,5-dichloropyridin-2-yloxy)phenylimino]methyl}phenol
;
_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                 95.318(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8981(7)
_cell_length_b                   11.7006(8)
_cell_length_c                   10.5034(5)
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.9
_cell_volume                     1700.67(17)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method       ω
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7882
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.8560
_exptl_absorpt_correction_T_min  0.8173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0397
_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)+(0.0376P)²+0.5849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                2186
_reflns_number_total             3107
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5335.cif
_cod_data_source_block           I
_cod_original_cell_volume        1700.67(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232504
_cod_database_fobs_code          2232504
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_symmetry_multiplicity
Cl Cl1 -0.24721(6) 0.26343(9) 1.31374(10) 0.1009(3) Uani d . 1 1
Cl Cl2 0.53771(6) 0.21299(7) 0.55024(6) 0.0716(2) Uani d . 1 1
Cl Cl3 0.41754(6) 0.53738(7) 0.20843(6) 0.0723(2) Uani d . 1 1
O O1 0.08837(14) 0.54210(18) 1.22171(19) 0.0727(6) Uani d . 1 1
H H1 0.1140 0.5196 1.1591 0.109 Uiso calc R 1 1
O O2 0.37377(13) 0.29274(16) 0.67705(16) 0.0629(5) Uani d . 1 1
N N1 0.11798(14) 0.40766(18) 1.03385(17) 0.0464(5) Uani d . 1 1
N N2 0.32327(15) 0.4354(2) 0.53329(19) 0.0570(6) Uani d . 1 1
C C1 0.01103(17) 0.4760(2) 1.2388(2) 0.0503(6) Uani d . 1 1
C C2 -0.0441(2) 0.5020(3) 1.3378(2) 0.0618(7) Uani d . 1 1
H H2 -0.0275 0.5646 1.3899 0.074 Uiso calc R 1 1
C C3 -0.1226(2) 0.4374(3) 1.3606(3) 0.0635(8) Uani d . 1 1
H H3 -0.1592 0.4560 1.4274 0.076 Uiso calc R 1 1
C C4 -0.14696(18) 0.3448(3) 1.2841(3) 0.0605(7) Uani d . 1 1
C C5 -0.09479(18) 0.3184(2) 1.1840(2) 0.0556(6) Uani d . 1 1
H H5 -0.1130 0.2563 1.1320 0.067 Uiso calc R 1 1
C C6 -0.01468(16) 0.3832(2) 1.1588(2) 0.0452(6) Uani d . 1 1
C C7 0.04132(17) 0.3533(2) 1.0541(2) 0.0479(6) Uani d . 1 1
H H7 0.0209 0.2932 1.0004 0.057 Uiso calc R 1 1
C C8 0.17777(16) 0.3761(2) 0.9376(2) 0.0439(6) Uani d . 1 1
C C9 0.16860(18) 0.2763(2) 0.8667(2) 0.0587(7) Uani d . 1 1
H H9 0.1192 0.2251 0.8796 0.070 Uiso calc R 1 1
C C10 0.23239(19) 0.2524(3) 0.7770(2) 0.0580(7) Uani d . 1 1
H H10 0.2258 0.1856 0.7290 0.070 Uiso calc R 1 1
C C11 0.30536(18) 0.3275(2) 0.7592(2) 0.0506(6) Uani d . 1 1
C C12 0.31653(19) 0.4262(2) 0.8286(3) 0.0605(7) Uani d . 1 1
H H12 0.3665 0.4766 0.8159 0.073 Uiso calc R 1 1
C C13 0.25235(18) 0.4498(2) 0.9179(2) 0.0545(6) Uani d . 1 1
H H13 0.2596 0.5167 0.9657 0.065 Uiso calc R 1 1
C C14 0.38386(18) 0.3526(2) 0.5682(2) 0.0483(6) Uani d . 1 1
C C15 0.45916(17) 0.3205(2) 0.4973(2) 0.0463(6) Uani d . 1 1
C C16 0.47057(17) 0.3767(2) 0.3851(2) 0.0475(6) Uani d . 1 1
H H16 0.5199 0.3571 0.3351 0.057 Uiso calc R 1 1
C C17 0.40660(18) 0.4631(2) 0.3490(2) 0.0495(6) Uani d . 1 1
C C18 0.33466(19) 0.4902(2) 0.4238(2) 0.0580(7) Uani d . 1 1
H H18 0.2921 0.5488 0.3978 0.070 Uiso calc R 1 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
C1 O1 H1 109.5
C14 O2 C11 119.80(19)
C7 N1 C8 122.9(2)
C14 N2 C18 118.0(2)
O1 C1 C2 118.6(2)
O1 C1 C6 121.8(2)
C2 C1 C6 119.6(2)
C3 C2 C1 121.1(3)
C3 C2 H2 119.4
C1 C2 H2 119.4
C2 C3 C4 119.5(3)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 120.6(3)
C5 C4 Cl1 120.3(2)
C3 C4 Cl1 119.0(2)
C4 C5 C6 120.9(3)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 118.2(2)
C5 C6 C7 120.6(2)
C1 C6 C7 121.2(2)
N1 C7 C6 121.5(2)
N1 C7 H7 119.2
C6 C7 H7 119.2
C13 C8 C9 118.7(2)
C13 C8 N1 116.3(2)
C9 C8 N1 125.0(2)
C10 C9 C8 120.3(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 119.6(3)
C11 C10 H10 120.2
C9 C10 H10 120.2
C12 C11 C10 121.2(2)
C12 C11 O2 121.6(2)
C10 C11 O2 116.9(2)
C11 C12 C13 118.9(2)
C11 C12 H12 120.6
C13 C12 H12 120.6
C8 C13 C12 121.2(2)
C8 C13 H13 119.4
C12 C13 H13 119.4
N2 C14 O2 120.1(2)
N2 C14 C15 123.0(2)
O2 C14 C15 116.9(2)
C16 C15 C14 118.9(2)
C16 C15 Cl2 120.45(18)
C14 C15 Cl2 120.63(18)
C15 C16 C17 117.8(2)
C15 C16 H16 121.1
C17 C16 H16 121.1
C18 C17 C16 120.0(2)
C18 C17 Cl3 120.1(2)
C16 C17 Cl3 119.89(19)
N2 C18 C17 122.3(2)
N2 C18 H18 118.8
C17 C18 H18 118.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.739(3)
Cl2 C15 1.724(2)
Cl3 C17 1.732(2)
O1 C1 1.349(3)
O1 H1 0.8200
O2 C14 1.359(3)
O2 C11 1.402(3)
N1 C7 1.275(3)
N1 C8 1.416(3)
N2 C14 1.314(3)
N2 C18 1.339(3)
C1 C2 1.381(3)
C1 C6 1.400(3)
C2 C3 1.366(4)
C2 H2 0.9300
C3 C4 1.372(4)
C3 H3 0.9300
C4 C5 1.366(3)
C5 C6 1.393(3)
C5 H5 0.9300
C6 C7 1.448(3)
C7 H7 0.9300
C8 C13 1.379(3)
C8 C9 1.384(3)
C9 C10 1.381(3)
C9 H9 0.9300
C10 C11 1.368(4)
C10 H10 0.9300
C11 C12 1.367(4)
C12 C13 1.381(3)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.391(3)
C15 C16 1.371(3)
C16 C17 1.376(3)
C16 H16 0.9300
C17 C18 1.365(3)
C18 H18 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.86 2.586(3) 146.8 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657170
