#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224394.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_2224394
loop_
_publ_author_name
'Xu, Li'
'Wu, Lei'
_publ_section_title
;
 4-Chloro-2-((E)-{3-[1-(hydroxyimino)ethyl]phenyl}iminomethyl)phenol
;
_journal_coeditor_code           PV2220
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3021
_journal_paper_doi               10.1107/S1600536809045942
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 Cl N2 O2'
_chemical_formula_moiety         'C15 H13 Cl N2 O2'
_chemical_formula_sum            'C15 H13 Cl N2 O2'
_chemical_formula_weight         288.72
_chemical_melting_point_gt       454
_chemical_melting_point_lt       456
_chemical_name_systematic
;
4-Chloro-2-((E)-{3-[1-(hydroxyimino)ethyl]phenyl}iminomethyl)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                 96.328(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7139(16)
_cell_length_b                   5.9983(6)
_cell_length_c                   13.3902(11)
_cell_measurement_reflns_used    1148
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.262
_cell_measurement_theta_min      3.062
_cell_volume                     1334.3(2)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6410
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.8933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0436
_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)+(0.0246P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                1398
_reflns_number_total             2349
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2220.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224394
_cod_database_fobs_code          2224394
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
Cl Cl1 0.47005(4) -0.34472(13) 0.16802(5) 0.0679(3) Uani d . 1 . .
N N1 0.04965(12) 1.3024(4) -0.03178(14) 0.0492(6) Uani d . 1 . .
N N2 0.25468(11) 0.4873(4) 0.02923(14) 0.0459(5) Uani d . 1 . .
O O1 0.01107(10) 1.4271(3) -0.11173(11) 0.0660(6) Uani d . 1 . .
H H1 -0.0105 1.5364 -0.0895 0.099 Uiso calc R 1 . .
O O2 0.29783(10) 0.2627(3) -0.12216(12) 0.0714(6) Uani d . 1 . .
H H2 0.2760 0.3628 -0.0934 0.107 Uiso calc R 1 . .
C C1 0.08207(16) 1.0646(5) -0.16879(17) 0.0649(9) Uani d . 1 . .
H H1A 0.0436 1.1557 -0.2087 0.097 Uiso calc R 1 . .
H H1B 0.0670 0.9107 -0.1768 0.097 Uiso calc R 1 . .
H H1C 0.1344 1.0862 -0.1903 0.097 Uiso calc R 1 . .
C C2 0.08394(13) 1.1288(4) -0.06072(16) 0.0397(6) Uani d . 1 . .
C C3 0.12822(12) 0.9899(4) 0.01858(16) 0.0368(6) Uani d . 1 . .
C C4 0.16997(12) 0.8025(4) -0.00603(17) 0.0414(6) Uani d . 1 . .
H H4 0.1693 0.7636 -0.0734 0.050 Uiso calc R 1 . .
C C5 0.21285(13) 0.6705(4) 0.06599(18) 0.0403(6) Uani d . 1 . .
C C6 0.21285(14) 0.7264(5) 0.16624(18) 0.0512(7) Uani d . 1 . .
H H6 0.2406 0.6389 0.2159 0.061 Uiso calc R 1 . .
C C7 0.17157(15) 0.9121(5) 0.19178(18) 0.0552(8) Uani d . 1 . .
H H7 0.1719 0.9499 0.2592 0.066 Uiso calc R 1 . .
C C8 0.12969(14) 1.0435(4) 0.11943(17) 0.0465(7) Uani d . 1 . .
H H8 0.1023 1.1688 0.1384 0.056 Uiso calc R 1 . .
C C9 0.29415(13) 0.3476(4) 0.08762(19) 0.0462(7) Uani d . 1 . .
H H9 0.2948 0.3651 0.1567 0.055 Uiso calc R 1 . .
C C10 0.33755(13) 0.1644(4) 0.04994(18) 0.0410(6) Uani d . 1 . .
C C11 0.33784(14) 0.1268(5) -0.05337(19) 0.0491(7) Uani d . 1 . .
C C12 0.37878(14) -0.0525(5) -0.08613(19) 0.0572(8) Uani d . 1 . .
H H12 0.3789 -0.0767 -0.1547 0.069 Uiso calc R 1 . .
C C13 0.41961(14) -0.1967(5) -0.0189(2) 0.0547(7) Uani d . 1 . .
H H13 0.4473 -0.3176 -0.0417 0.066 Uiso calc R 1 . .
C C14 0.41926(13) -0.1606(4) 0.08297(19) 0.0459(7) Uani d . 1 . .
C C15 0.37940(13) 0.0169(4) 0.11697(18) 0.0462(7) Uani d . 1 . .
H H15 0.3801 0.0399 0.1857 0.055 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'
O O 0.0106 0.0060 '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'
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
C2 N1 O1 . . 112.91(19) ?
C9 N2 C5 . . 122.4(2) ?
N1 O1 H1 . . 109.5 ?
C11 O2 H2 . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C3 . . 116.7(2) ?
N1 C2 C1 . . 123.0(2) ?
C3 C2 C1 . . 120.3(2) ?
C4 C3 C8 . . 117.8(2) ?
C4 C3 C2 . . 120.8(2) ?
C8 C3 C2 . . 121.4(2) ?
C3 C4 C5 . . 122.4(2) ?
C3 C4 H4 . . 118.8 ?
C5 C4 H4 . . 118.8 ?
C6 C5 C4 . . 118.8(2) ?
C6 C5 N2 . . 125.2(2) ?
C4 C5 N2 . . 116.0(2) ?
C7 C6 C5 . . 119.5(2) ?
C7 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C6 C7 C8 . . 121.3(2) ?
C6 C7 H7 . . 119.4 ?
C8 C7 H7 . . 119.4 ?
C7 C8 C3 . . 120.3(2) ?
C7 C8 H8 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
N2 C9 C10 . . 122.2(2) ?
N2 C9 H9 . . 118.9 ?
C10 C9 H9 . . 118.9 ?
C15 C10 C11 . . 118.5(2) ?
C15 C10 C9 . . 119.8(2) ?
C11 C10 C9 . . 121.7(2) ?
O2 C11 C12 . . 118.8(2) ?
O2 C11 C10 . . 121.4(2) ?
C12 C11 C10 . . 119.8(2) ?
C11 C12 C13 . . 120.8(2) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C14 . . 119.5(3) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C15 C14 C13 . . 120.6(2) ?
C15 C14 Cl1 . . 120.0(2) ?
C13 C14 Cl1 . . 119.5(2) ?
C14 C15 C10 . . 120.7(2) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
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
Cl1 C14 . 1.739(2) ?
N1 C2 . 1.269(3) ?
N1 O1 . 1.403(2) ?
N2 C9 . 1.279(3) ?
N2 C5 . 1.419(3) ?
O1 H1 . 0.8200 ?
O2 C11 . 1.351(3) ?
O2 H2 . 0.8200 ?
C1 C2 . 1.495(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.482(3) ?
C3 C4 . 1.382(3) ?
C3 C8 . 1.386(3) ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C6 C7 . 1.373(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.379(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.439(3) ?
C9 H9 . 0.9300 ?
C10 C15 . 1.393(3) ?
C10 C11 . 1.402(3) ?
C11 C12 . 1.372(3) ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.381(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.361(3) ?
C15 H15 . 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
_geom_hbond_publ_flag
O2 H2 N2 . 0.82 1.87 2.601(3) 147 y
O1 H1 N1 3_585 0.82 2.06 2.789(3) 149 y
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 N1 C2 C3 . . . . 178.37(18) ?
O1 N1 C2 C1 . . . . -0.7(3) ?
N1 C2 C3 C4 . . . . -177.5(2) ?
C1 C2 C3 C4 . . . . 1.6(3) ?
N1 C2 C3 C8 . . . . 2.1(3) ?
C1 C2 C3 C8 . . . . -178.8(2) ?
C8 C3 C4 C5 . . . . -0.5(3) ?
C2 C3 C4 C5 . . . . 179.1(2) ?
C3 C4 C5 C6 . . . . 1.0(3) ?
C3 C4 C5 N2 . . . . -178.2(2) ?
C9 N2 C5 C6 . . . . 3.5(4) ?
C9 N2 C5 C4 . . . . -177.4(2) ?
C4 C5 C6 C7 . . . . -0.9(4) ?
N2 C5 C6 C7 . . . . 178.2(2) ?
C5 C6 C7 C8 . . . . 0.3(4) ?
C6 C7 C8 C3 . . . . 0.2(4) ?
C4 C3 C8 C7 . . . . -0.1(3) ?
C2 C3 C8 C7 . . . . -179.7(2) ?
C5 N2 C9 C10 . . . . -178.9(2) ?
N2 C9 C10 C15 . . . . -179.8(2) ?
N2 C9 C10 C11 . . . . -1.0(4) ?
C15 C10 C11 O2 . . . . 179.4(2) ?
C9 C10 C11 O2 . . . . 0.6(4) ?
C15 C10 C11 C12 . . . . 0.1(4) ?
C9 C10 C11 C12 . . . . -178.8(2) ?
O2 C11 C12 C13 . . . . -179.3(2) ?
C10 C11 C12 C13 . . . . 0.1(4) ?
C11 C12 C13 C14 . . . . 0.1(4) ?
C12 C13 C14 C15 . . . . -0.5(4) ?
C12 C13 C14 Cl1 . . . . 179.35(19) ?
C13 C14 C15 C10 . . . . 0.6(4) ?
Cl1 C14 C15 C10 . . . . -179.18(17) ?
C11 C10 C15 C14 . . . . -0.4(4) ?
C9 C10 C15 C14 . . . . 178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743765
