#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230663.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_2230663
loop_
_publ_author_name
'Sun, Li-Xia'
'Yu, Yun-Dan'
'Wei, Guo-Ying'
_publ_section_title
;
 4-[(E)-(2,3-Dichlorobenzylidene)amino]phenol
;
_journal_coeditor_code           HB5895
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1564
_journal_paper_doi               10.1107/S1600536811019933
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H9 Cl2 N O'
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11
_chemical_name_systematic
;
4-[(E)-(2,3-Dichlorobenzylidene)amino]phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.049(4)
_cell_length_b                   10.038(6)
_cell_length_c                   19.645(12)
_cell_measurement_reflns_used    2869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.28
_cell_volume                     1192.8(13)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4853
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.143
_refine_ls_abs_structure_details 'Flack (1983), 869 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       0.073(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0301
_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)+(0.0269P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                1998
_reflns_number_total             2184
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5895.cif
_cod_data_source_block           I
_cod_database_code               2230663
_cod_database_fobs_code          2230663
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6782(4) 0.13161(18) 0.30064(9) 0.0315(5) Uani d . 1 1 . .
C C2 0.8717(4) 0.2032(2) 0.29247(10) 0.0380(5) Uani d . 1 1 . .
H H2 0.9883 0.1903 0.3226 0.046 Uiso calc R 1 1 . .
C C3 0.8932(4) 0.2937(2) 0.23991(10) 0.0353(5) Uani d . 1 1 . .
H H3 1.0241 0.3413 0.2347 0.042 Uiso calc R 1 1 . .
C C4 0.7192(3) 0.31355(18) 0.19496(10) 0.0305(5) Uani d . 1 1 . .
C C5 0.5261(4) 0.2441(2) 0.20450(11) 0.0389(5) Uani d . 1 1 . .
H H5 0.4074 0.2593 0.1754 0.047 Uiso calc R 1 1 . .
C C6 0.5046(4) 0.1522(2) 0.25642(11) 0.0380(5) Uani d . 1 1 . .
H H6 0.3739 0.1045 0.2615 0.046 Uiso calc R 1 1 . .
C C7 0.9040(4) 0.3995(2) 0.10174(10) 0.0305(5) Uani d . 1 1 . .
H H7 1.0160 0.3406 0.1138 0.037 Uiso calc R 1 1 . .
C C8 0.9356(3) 0.48183(19) 0.04113(10) 0.0302(5) Uani d . 1 1 . .
C C9 0.7862(4) 0.5815(2) 0.02412(11) 0.0404(5) Uani d . 1 1 . .
H H9 0.6685 0.5997 0.0531 0.049 Uiso calc R 1 1 . .
C C10 0.8097(4) 0.6539(2) -0.03507(13) 0.0528(6) Uani d . 1 1 . .
H H10 0.7081 0.7203 -0.0457 0.063 Uiso calc R 1 1 . .
C C11 0.9837(5) 0.6281(2) -0.07860(12) 0.0502(6) Uani d . 1 1 . .
H H11 0.9987 0.6761 -0.1188 0.060 Uiso calc R 1 1 . .
C C12 1.1338(4) 0.5315(2) -0.06226(10) 0.0392(5) Uani d . 1 1 . .
C C13 1.1149(4) 0.45927(17) -0.00259(10) 0.0317(5) Uani d . 1 1 . .
Cl Cl1 1.35264(12) 0.50375(7) -0.11774(3) 0.0628(2) Uani d . 1 1 . .
Cl Cl2 1.31056(9) 0.33967(5) 0.01639(3) 0.04412(18) Uani d . 1 1 . .
N N1 0.7322(3) 0.40395(17) 0.13882(8) 0.0321(4) Uani d . 1 1 . .
O O1 0.6681(3) 0.04560(15) 0.35434(8) 0.0447(4) Uani d . 1 1 . .
H H1 0.5510 0.0045 0.3531 0.067 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'
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
O1 C1 C6 . . 123.22(19) ?
O1 C1 C2 . . 117.18(18) ?
C6 C1 C2 . . 119.58(18) ?
C3 C2 C1 . . 120.57(19) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C2 C3 C4 . . 119.86(19) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C5 C4 C3 . . 119.06(18) ?
C5 C4 N1 . . 118.29(18) ?
C3 C4 N1 . . 122.66(17) ?
C4 C5 C6 . . 121.3(2) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C1 C6 C5 . . 119.6(2) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
N1 C7 C8 . . 123.66(19) ?
N1 C7 H7 . . 118.2 ?
C8 C7 H7 . . 118.2 ?
C9 C8 C13 . . 118.18(19) ?
C9 C8 C7 . . 121.20(19) ?
C13 C8 C7 . . 120.60(18) ?
C10 C9 C8 . . 121.0(2) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 120.1(2) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.6(2) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 C13 . . 121.1(2) ?
C11 C12 Cl1 . . 118.21(17) ?
C13 C12 Cl1 . . 120.71(18) ?
C12 C13 C8 . . 119.9(2) ?
C12 C13 Cl2 . . 119.40(17) ?
C8 C13 Cl2 . . 120.68(15) ?
C7 N1 C4 . . 117.70(17) ?
C1 O1 H1 . . 109.5 ?
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 O1 . 1.365(2) ?
C1 C6 . 1.379(3) ?
C1 C2 . 1.382(3) ?
C2 C3 . 1.382(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.388(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(3) ?
C4 N1 . 1.430(2) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.270(3) ?
C7 C8 . 1.462(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.390(3) ?
C8 C13 . 1.402(3) ?
C9 C10 . 1.378(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.366(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.383(3) ?
C12 Cl1 . 1.737(2) ?
C13 Cl2 . 1.727(2) ?
O1 H1 . 0.8200 ?
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 3_645 0.82 1.99 2.811(3) 174
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
O1 C1 C2 C3 . . . . -179.00(19) ?
C6 C1 C2 C3 . . . . -0.8(3) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 1.3(3) ?
C2 C3 C4 N1 . . . . -178.85(18) ?
C3 C4 C5 C6 . . . . -2.1(3) ?
N1 C4 C5 C6 . . . . 177.97(19) ?
O1 C1 C6 C5 . . . . 178.0(2) ?
C2 C1 C6 C5 . . . . 0.0(3) ?
C4 C5 C6 C1 . . . . 1.5(3) ?
N1 C7 C8 C9 . . . . 6.8(3) ?
N1 C7 C8 C13 . . . . -171.26(19) ?
C13 C8 C9 C10 . . . . 1.8(3) ?
C7 C8 C9 C10 . . . . -176.3(2) ?
C8 C9 C10 C11 . . . . -0.1(4) ?
C9 C10 C11 C12 . . . . -0.8(4) ?
C10 C11 C12 C13 . . . . -0.2(3) ?
C10 C11 C12 Cl1 . . . . -179.07(19) ?
C11 C12 C13 C8 . . . . 2.0(3) ?
Cl1 C12 C13 C8 . . . . -179.16(15) ?
C11 C12 C13 Cl2 . . . . -179.20(17) ?
Cl1 C12 C13 Cl2 . . . . -0.4(2) ?
C9 C8 C13 C12 . . . . -2.8(3) ?
C7 C8 C13 C12 . . . . 175.34(18) ?
C9 C8 C13 Cl2 . . . . 178.46(15) ?
C7 C8 C13 Cl2 . . . . -3.4(3) ?
C8 C7 N1 C4 . . . . 177.33(18) ?
C5 C4 N1 C7 . . . . -133.5(2) ?
C3 C4 N1 C7 . . . . 46.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656768
