#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013988.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_2013988
loop_
_publ_author_name
'Kos̨ar, Bas̨ak'
'Büyükgüngör, Orhan'
'Albayrak, Çiğdem'
'Odabaşoğlu, Mustafa'
_publ_section_title
;
 3-Hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone and
 2-hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o458
_journal_page_last               o460
_journal_paper_doi               10.1107/S0108270104010832
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H11 N O3'
_chemical_formula_moiety         'C13 H11 N O3'
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23
_chemical_melting_point          465.0(10)
_chemical_name_systematic
;
2-Hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.693(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6440(8)
_cell_length_b                   8.3499(3)
_cell_length_c                   20.1529(12)
_cell_measurement_reflns_used    22130
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      1.62
_cell_volume                     2113.2(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS 2'
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32250
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shapeless
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4610
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      2.501
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0341
_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)+(0.0592P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                3305
_reflns_number_total             4610
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1477.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '464-466' was changed to '465.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '464-466' was changed to '465.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013988
_cod_database_fobs_code          2013988
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_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
_atom_site_type_symbol
C1 -0.0008(2) 0.3052(4) 0.62303(14) 0.0369(6) Uani d . 1 . . C
C2 -0.0798(3) 0.1913(4) 0.61224(15) 0.0421(7) Uani d . 1 . . C
H2 -0.0936 0.1426 0.5706 0.051 Uiso calc RD 1 . . H
C3 -0.1385(3) 0.1494(4) 0.66353(16) 0.0428(7) Uani d . 1 . . C
H3 -0.1913 0.0718 0.6564 0.051 Uiso calc R 1 . . H
C4 -0.1189(2) 0.2224(4) 0.72512(15) 0.0393(7) Uani d . 1 . . C
C5 -0.0382(3) 0.3334(4) 0.73661(16) 0.0464(8) Uani d . 1 . . C
H5 -0.0232 0.3803 0.7785 0.056 Uiso calc R 1 . . H
C6 0.0202(3) 0.3746(4) 0.68545(16) 0.0456(8) Uani d . 1 . . C
H6 0.0743 0.4500 0.6931 0.055 Uiso calc R 1 . . H
C7 0.0655(3) 0.2914(4) 0.51594(15) 0.0412(7) Uani d . 1 . . C
C8 0.1307(2) 0.3521(4) 0.46839(14) 0.0387(7) Uani d . 1 . . C
C9 0.1352(3) 0.2697(4) 0.40780(15) 0.0472(8) Uani d . 1 . . C
H9 0.0929 0.1796 0.3980 0.057 Uiso calc R 1 . . H
C10 0.2014(3) 0.3213(4) 0.36333(16) 0.0502(8) Uani d . 1 . . C
H10 0.2036 0.2667 0.3233 0.060 Uiso calc R 1 . . H
C11 0.2656(3) 0.4555(4) 0.37768(15) 0.0461(8) Uani d . 1 . . C
H11 0.3113 0.4887 0.3474 0.055 Uiso calc R 1 . . H
C12 0.2621(2) 0.5391(4) 0.43600(15) 0.0413(7) Uani d . 1 . . C
C13 0.1930(2) 0.4912(4) 0.48274(14) 0.0388(7) Uani d . 1 . . C
C14 0.4561(2) 0.1462(4) 0.40719(14) 0.0384(7) Uani d . 1 . . C
C15 0.5280(3) 0.2697(4) 0.40289(15) 0.0436(7) Uani d . 1 . . C
H15 0.5396 0.3442 0.4372 0.052 Uiso calc R 1 . . H
C16 0.5825(3) 0.2822(4) 0.34782(16) 0.0440(7) Uani d . 1 . . C
H16 0.6315 0.3645 0.3453 0.053 Uiso calc R 1 . . H
C17 0.5646(2) 0.1726(4) 0.29609(15) 0.0406(7) Uani d . 1 . . C
C18 0.4926(3) 0.0501(4) 0.30019(15) 0.0470(8) Uani d . 1 . . C
H18 0.4800 -0.0232 0.2654 0.056 Uiso calc R 1 . . H
C19 0.4394(3) 0.0362(4) 0.35565(16) 0.0461(8) Uani d . 1 . . C
H19 0.3919 -0.0478 0.3586 0.055 Uiso calc R 1 . . H
C20 0.4032(3) 0.2071(4) 0.51721(16) 0.0441(7) Uani d . 1 . . C
C21 0.3415(3) 0.1677(4) 0.56900(15) 0.0407(7) Uani d . 1 . . C
C22 0.3480(3) 0.2610(4) 0.62764(17) 0.0515(8) Uani d . 1 . . C
H22 0.3925 0.3500 0.6319 0.062 Uiso calc R 1 . . H
C23 0.2899(3) 0.2224(4) 0.67815(17) 0.0537(9) Uani d . 1 . . C
H23 0.2942 0.2859 0.7163 0.064 Uiso calc R 1 . . H
C24 0.2241(3) 0.0878(4) 0.67287(16) 0.0486(8) Uani d . 1 . . C
H24 0.1846 0.0618 0.7075 0.058 Uiso calc R 1 . . H
C25 0.2175(2) -0.0057(4) 0.61718(15) 0.0424(7) Uani d . 1 . . C
C26 0.2743(2) 0.0304(4) 0.56259(14) 0.0391(7) Uani d . 1 . . C
N1 0.0604(2) 0.3593(3) 0.57287(12) 0.0401(6) Uani d . 1 . . N
N2 0.3989(2) 0.1228(3) 0.46264(12) 0.0414(6) Uani d . 1 . . N
O1 -0.18331(19) 0.1816(3) 0.77327(12) 0.0491(6) Uani d . 1 . . O
O2 0.1889(2) 0.5753(3) 0.53811(11) 0.0508(6) Uani d D 1 . . O
O3 0.3262(2) 0.6695(3) 0.44918(13) 0.0561(7) Uani d . 1 . . O
O4 0.6154(2) 0.1805(3) 0.24005(12) 0.0532(6) Uani d . 1 . . O
O5 0.2637(2) -0.0606(3) 0.50998(10) 0.0493(6) Uani d . 1 . . O
O6 0.1550(2) -0.1422(3) 0.61175(12) 0.0540(6) Uani d . 1 . . O
H1 0.098(5) 0.448(7) 0.580(3) 0.14(2) Uiso d D 1 . . H
H4 0.343(4) 0.031(6) 0.464(2) 0.083(14) Uiso d . 1 . . H
H7 0.025(3) 0.192(4) 0.5044(17) 0.046(9) Uiso d . 1 . . H
H20 0.452(3) 0.298(5) 0.5241(18) 0.057(10) Uiso d . 1 . . H
H33 0.301(4) 0.733(7) 0.481(3) 0.103(18) Uiso d . 1 . . H
H44 0.676(4) 0.240(7) 0.249(2) 0.097(17) Uiso d . 1 . . H
H66 0.169(4) -0.198(7) 0.577(3) 0.101(18) Uiso d . 1 . . H
H77 -0.164(4) 0.243(6) 0.810(2) 0.089(15) Uiso d . 1 . . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 119.4(3) ?
C2 C1 N1 123.6(3) ?
C6 C1 N1 116.9(3) ?
C1 C2 C3 119.9(3) ?
C1 C2 H2 120.1 ?
C3 C2 H2 120.1 ?
C4 C3 C2 120.3(3) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C5 C4 C3 120.0(3) ?
C5 C4 O1 122.3(3) ?
C3 C4 O1 117.7(3) ?
C4 C5 C6 119.5(3) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
C5 C6 C1 120.9(3) ?
C5 C6 H6 119.6 ?
C1 C6 H6 119.6 ?
N1 C7 C8 122.3(3) ?
N1 C7 H7 120(2) ?
C8 C7 H7 118(2) ?
C9 C8 C13 120.0(3) ?
C9 C8 C7 119.5(3) yes
C13 C8 C7 120.4(3) yes
C10 C9 C8 120.3(3) ?
C10 C9 H9 119.9 ?
C8 C9 H9 119.9 ?
C9 C10 C11 120.3(3) ?
C9 C10 H10 119.9 ?
C11 C10 H10 119.9 ?
C12 C11 C10 120.7(3) ?
C12 C11 H11 119.7 ?
C10 C11 H11 119.7 ?
O3 C12 C11 119.6(3) ?
O3 C12 C13 119.7(3) ?
C11 C12 C13 120.7(3) ?
O2 C13 C12 120.0(3) yes
O2 C13 C8 122.1(3) yes
C12 C13 C8 117.9(3) ?
C15 C14 C19 119.4(3) ?
C15 C14 N2 123.6(3) ?
C19 C14 N2 117.0(3) ?
C16 C15 C14 120.1(3) ?
C16 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
C15 C16 C17 120.2(3) ?
C15 C16 H16 119.9 ?
C17 C16 H16 119.9 ?
O4 C17 C18 117.6(3) ?
O4 C17 C16 122.6(3) ?
C18 C17 C16 119.8(3) ?
C19 C18 C17 120.0(3) ?
C19 C18 H18 120.0 ?
C17 C18 H18 120.0 ?
C18 C19 C14 120.5(3) ?
C18 C19 H19 119.7 ?
C14 C19 H19 119.7 ?
N2 C20 C21 121.7(3) ?
N2 C20 H20 120(2) ?
C21 C20 H20 118(2) ?
C22 C21 C20 120.5(3) ?
C22 C21 C26 119.8(3) ?
C20 C21 C26 119.7(3) ?
C23 C22 C21 120.8(3) ?
C23 C22 H22 119.6 ?
C21 C22 H22 119.6 ?
C22 C23 C24 120.2(3) ?
C22 C23 H23 119.9 ?
C24 C23 H23 119.9 ?
C25 C24 C23 120.2(3) ?
C25 C24 H24 119.9 ?
C23 C24 H24 119.9 ?
C24 C25 O6 121.1(3) ?
C24 C25 C26 122.0(3) ?
O6 C25 C26 116.8(3) ?
O5 C26 C25 119.8(3) ?
O5 C26 C21 123.3(3) ?
C25 C26 C21 116.9(3) ?
C7 N1 C1 125.7(3) ?
C7 N1 H1 115(4) ?
C1 N1 H1 119(4) ?
C20 N2 C14 128.2(3) ?
C20 N2 H4 110(2) ?
C14 N2 H4 122(2) ?
C4 O1 H77 107(3) ?
C12 O3 H33 111(3) ?
C17 O4 H44 109(3) ?
C25 O6 H66 110(4) ?
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 C2 . 1.378(4) ?
C1 C6 . 1.382(4) ?
C1 N1 . 1.416(4) yes
C2 C3 . 1.386(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(5) ?
C4 O1 . 1.381(3) yes
C5 C6 . 1.380(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.288(4) yes
C7 C8 . 1.428(4) yes
C7 H7 . 0.99(4) ?
C8 C9 . 1.409(4) ?
C8 C13 . 1.415(4) ?
C9 C10 . 1.365(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.394(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.372(4) ?
C11 H11 . 0.9300 ?
C12 O3 . 1.365(4) yes
C12 C13 . 1.415(4) ?
C13 O2 . 1.324(4) yes
C14 C15 . 1.384(4) ?
C14 C19 . 1.384(4) ?
C14 N2 . 1.414(4) ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.386(5) ?
C16 H16 . 0.9300 ?
C17 O4 . 1.364(4) ?
C17 C18 . 1.378(5) ?
C18 C19 . 1.375(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 N2 . 1.301(4) ?
C20 C21 . 1.413(4) ?
C20 H20 . 0.98(4) ?
C21 C22 . 1.410(4) ?
C21 C26 . 1.423(4) ?
C22 C23 . 1.361(5) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.396(5) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.362(5) ?
C24 H24 . 0.9300 ?
C25 O6 . 1.384(4) ?
C25 C26 . 1.415(4) ?
C26 O5 . 1.298(4) ?
N1 H1 . 0.88(5) ?
N2 H4 . 1.04(5) ?
O1 H77 . 0.90(5) ?
O3 H33 . 0.92(5) ?
O4 H44 . 0.91(5) ?
O6 H66 . 0.88(5) ?
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
N2 H4 O5 . 1.04(5) 1.64(5) 2.561(3) 145(4)
N1 H1 O2 . 0.88(5) 1.84(4) 2.578(3) 141(6)
O6 H66 O5 . 0.88(5) 2.22(5) 2.686(3) 112(4)
O1 H77 O6 2_556 0.90(5) 1.85(5) 2.733(4) 167(4)
O6 H66 O2 1_545 0.88(5) 2.07(6) 2.846(4) 146(5)
O4 H44 O1 4_665 0.91(5) 1.90(5) 2.803(4) 167(5)
O3 H33 O5 1_565 0.92(5) 1.89(6) 2.727(4) 150(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
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(5) ?
N1 C1 C2 C3 -177.6(3) ?
C1 C2 C3 C4 0.6(5) ?
C2 C3 C4 C5 -2.2(5) ?
C2 C3 C4 O1 176.9(3) ?
C3 C4 C5 C6 2.1(5) ?
O1 C4 C5 C6 -177.0(3) ?
C4 C5 C6 C1 -0.4(5) ?
C2 C1 C6 C5 -1.2(5) ?
N1 C1 C6 C5 177.6(3) ?
N1 C7 C8 C9 178.2(3) ?
N1 C7 C8 C13 0.2(5) yes
C13 C8 C9 C10 1.4(5) ?
C7 C8 C9 C10 -176.5(3) ?
C8 C9 C10 C11 0.4(5) ?
C9 C10 C11 C12 -1.1(5) ?
C10 C11 C12 O3 179.5(3) ?
C10 C11 C12 C13 -0.2(5) ?
O3 C12 C13 O2 1.8(5) ?
C11 C12 C13 O2 -178.5(3) ?
O3 C12 C13 C8 -177.7(3) ?
C11 C12 C13 C8 2.0(5) ?
C9 C8 C13 O2 177.9(3) ?
C7 C8 C13 O2 -4.1(5) ?
C9 C8 C13 C12 -2.6(5) ?
C7 C8 C13 C12 175.4(3) ?
C19 C14 C15 C16 -0.2(5) ?
N2 C14 C15 C16 178.5(3) ?
C14 C15 C16 C17 0.8(5) ?
C15 C16 C17 O4 179.2(3) ?
C15 C16 C17 C18 -0.5(5) ?
O4 C17 C18 C19 179.8(3) ?
C16 C17 C18 C19 -0.5(5) ?
C17 C18 C19 C14 1.2(5) ?
C15 C14 C19 C18 -0.8(5) ?
N2 C14 C19 C18 -179.6(3) ?
N2 C20 C21 C22 179.8(3) ?
N2 C20 C21 C26 1.4(5) yes
C20 C21 C22 C23 -179.1(3) ?
C26 C21 C22 C23 -0.6(5) ?
C21 C22 C23 C24 1.0(6) ?
C22 C23 C24 C25 -0.1(5) ?
C23 C24 C25 O6 178.2(3) ?
C23 C24 C25 C26 -1.2(5) ?
C24 C25 C26 O5 -178.6(3) ?
O6 C25 C26 O5 2.0(4) ?
C24 C25 C26 C21 1.5(5) ?
O6 C25 C26 C21 -177.9(3) ?
C22 C21 C26 O5 179.5(3) ?
C20 C21 C26 O5 -2.0(5) ?
C22 C21 C26 C25 -0.6(5) ?
C20 C21 C26 C25 177.9(3) ?
C8 C7 N1 C1 -178.9(3) ?
C2 C1 N1 C7 -13.9(5) ?
C6 C1 N1 C7 167.4(3) ?
C21 C20 N2 C14 -179.3(3) ?
C15 C14 N2 C20 -0.5(5) ?
C19 C14 N2 C20 178.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12998665
