#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225906.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_2225906
loop_
_publ_author_name
'Eltayeb, Naser Eltaher'
'Teoh, Siang Guan'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-4-Chloro-2-[(2-hydroxyphenyl)iminomethyl]phenol
;
_journal_coeditor_code           IS2534
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1065
_journal_page_last               o1066
_journal_paper_doi               10.1107/S160053681001233X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H10 Cl N O2'
_chemical_formula_moiety         'C13 H10 Cl N O2'
_chemical_formula_sum            'C13 H10 Cl N O2'
_chemical_formula_weight         247.67
_chemical_name_common
;
(E)-4-Chloro-2-[(2-hydroxyphenyl)iminomethyl]phenol
;
_chemical_name_systematic
;
(E)-4-Chloro-2-[(2-hydroxyphenylimino)methyl]phenol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.980(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.6681(9)
_cell_length_b                   18.509(3)
_cell_length_c                   6.2118(11)
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      4.37
_cell_volume                     536.63(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL  (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX Duo CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4593
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         4.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.469
_refine_ls_abs_structure_details 'Flack (1983), 1125 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0756P)²+0.0404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                2569
_reflns_number_total             2680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is2534.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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225906
_cod_database_fobs_code          2225906
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.02845(11) 1.08595(3) 0.36240(8) 0.01689(14) Uani d . 1 . .
O O1 1.1428(4) 0.82828(9) 0.5209(2) 0.0167(3) Uani d . 1 . .
H H1O1 1.2817 0.8379 0.5983 0.025 Uiso calc R 1 . .
O O2 0.5318(4) 0.86922(9) -0.2123(2) 0.0151(3) Uani d . 1 . .
H H1O2 0.6550 0.8463 -0.1462 0.018 Uiso calc R 1 . .
N N1 0.8674(4) 0.83076(10) 0.1062(3) 0.0116(3) Uani d . 1 . .
C C1 1.0806(4) 0.78021(11) 0.1679(3) 0.0113(4) Uani d . 1 . .
C C2 1.2187(4) 0.77923(11) 0.3724(3) 0.0119(4) Uani d . 1 . .
C C3 1.4270(5) 0.72625(12) 0.4139(3) 0.0144(4) Uani d . 1 . .
H H3 1.5136 0.7236 0.5496 0.017 Uiso calc R 1 . .
C C4 1.5066(5) 0.67719(12) 0.2539(4) 0.0157(4) Uani d . 1 . .
H H4 1.6481 0.6430 0.2828 0.019 Uiso calc R 1 . .
C C5 1.3732(5) 0.67964(12) 0.0506(4) 0.0147(4) Uani d . 1 . .
H H5 1.4255 0.6471 -0.0559 0.018 Uiso calc R 1 . .
C C6 1.1629(5) 0.73071(12) 0.0089(3) 0.0140(4) Uani d . 1 . .
H H6 1.0747 0.7323 -0.1264 0.017 Uiso calc R 1 . .
C C7 0.7386(5) 0.87972(12) 0.2228(3) 0.0122(4) Uani d . 1 . .
H H7 0.7886 0.8845 0.3677 0.015 Uiso calc R 1 . .
C C8 0.5237(5) 0.92579(11) 0.1321(3) 0.0114(4) Uani d . 1 . .
C C9 0.4240(5) 0.91833(11) -0.0859(3) 0.0115(4) Uani d . 1 . .
C C10 0.2019(5) 0.96567(12) -0.1572(3) 0.0132(4) Uani d . 1 . .
H H10 0.1328 0.9622 -0.2981 0.016 Uiso calc R 1 . .
C C11 0.0865(5) 1.01690(12) -0.0213(3) 0.0136(4) Uani d . 1 . .
H H11 -0.0572 1.0476 -0.0720 0.016 Uiso calc R 1 . .
C C12 0.1857(5) 1.02276(11) 0.1934(3) 0.0127(4) Uani d . 1 . .
C C13 0.4000(5) 0.97834(12) 0.2706(3) 0.0124(4) Uani d . 1 . .
H H13 0.4641 0.9825 0.4126 0.015 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1O1 . . 109.5 ?
C9 O2 H1O2 . . 109.5 ?
C7 N1 C1 . . 129.38(18) ?
C6 C1 N1 . . 116.14(18) ?
C6 C1 C2 . . 119.79(18) ?
N1 C1 C2 . . 124.01(19) ?
O1 C2 C3 . . 122.39(18) ?
O1 C2 C1 . . 119.04(18) ?
C3 C2 C1 . . 118.56(19) ?
C4 C3 C2 . . 120.96(19) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C6 C5 C4 . . 119.6(2) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 121.0(2) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N1 C7 C8 . . 121.39(19) ?
N1 C7 H7 . . 119.3 ?
C8 C7 H7 . . 119.3 ?
C7 C8 C13 . . 117.29(18) ?
C7 C8 C9 . . 122.13(19) ?
C13 C8 C9 . . 120.52(18) ?
O2 C9 C10 . . 121.83(18) ?
O2 C9 C8 . . 120.86(18) ?
C10 C9 C8 . . 117.30(18) ?
C11 C10 C9 . . 121.41(18) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 120.33(19) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 120.7(2) ?
C13 C12 Cl1 . . 120.17(16) ?
C11 C12 Cl1 . . 119.16(17) ?
C12 C13 C8 . . 119.77(19) ?
C12 C13 H13 . . 120.1 ?
C8 C13 H13 . . 120.1 ?
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 C12 . 1.742(2) ?
O1 C2 . 1.346(3) ?
O1 H1O1 . 0.8200 ?
O2 C9 . 1.308(3) ?
O2 H1O2 . 0.8200 ?
N1 C7 . 1.312(3) ?
N1 C1 . 1.414(3) ?
C1 C6 . 1.405(3) ?
C1 C2 . 1.415(3) ?
C2 C3 . 1.402(3) ?
C3 C4 . 1.401(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.425(3) ?
C7 H7 . 0.9300 ?
C8 C13 . 1.427(3) ?
C8 C9 . 1.431(3) ?
C9 C10 . 1.422(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.408(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(3) ?
C13 H13 . 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
O1 H1O1 O2 1_656 0.82 1.74 2.553(2) 169 y
O2 H1O2 N1 1_555 0.82 1.86 2.602(2) 149 y
C7 H7 O1 1_555 0.93 2.16 2.789(3) 124 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
C7 N1 C1 C6 . . . . 175.5(2) ?
C7 N1 C1 C2 . . . . -7.2(4) ?
C6 C1 C2 O1 . . . . 178.20(19) ?
N1 C1 C2 O1 . . . . 1.0(3) ?
C6 C1 C2 C3 . . . . -2.8(3) ?
N1 C1 C2 C3 . . . . 180.0(2) ?
O1 C2 C3 C4 . . . . -178.3(2) ?
C1 C2 C3 C4 . . . . 2.8(3) ?
C2 C3 C4 C5 . . . . -1.4(3) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
N1 C1 C6 C5 . . . . 178.9(2) ?
C2 C1 C6 C5 . . . . 1.5(3) ?
C1 N1 C7 C8 . . . . -179.2(2) ?
N1 C7 C8 C13 . . . . -178.77(19) ?
N1 C7 C8 C9 . . . . 4.0(3) ?
C7 C8 C9 O2 . . . . -1.3(3) ?
C13 C8 C9 O2 . . . . -178.44(19) ?
C7 C8 C9 C10 . . . . 177.9(2) ?
C13 C8 C9 C10 . . . . 0.8(3) ?
O2 C9 C10 C11 . . . . 179.1(2) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
C10 C11 C12 C13 . . . . 0.6(3) ?
C10 C11 C12 Cl1 . . . . -178.08(17) ?
C11 C12 C13 C8 . . . . 0.1(3) ?
Cl1 C12 C13 C8 . . . . 178.79(15) ?
C7 C8 C13 C12 . . . . -178.1(2) ?
C9 C8 C13 C12 . . . . -0.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21504423
