#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/67/2206734.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_2206734
loop_
_publ_author_name
'S̨ahin, Onur'
'Albayrak, Çiǧdem'
'Odabas̨oğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (Z)-3-Hydroxy-6-[(2-methoxyphenylamino)methylene]cyclohexa-2,4-dienone
;
_journal_coeditor_code           KP6061
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2859
_journal_page_last               o2861
_journal_paper_doi               10.1107/S1600536805024189
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H13 N O3'
_chemical_formula_moiety         'C14 H13 N O3'
_chemical_formula_sum            'C14 H13 N O3'
_chemical_formula_weight         243.25
_chemical_melting_point          .423E-305
_chemical_name_systematic
;
(Z)-3-hydroxy-6-[(2-methoxyphenylamino)methylene]cyclohexa-2,4-dienone
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3391(7)
_cell_length_b                   11.1748(15)
_cell_length_c                   13.8056(19)
_cell_measurement_reflns_used    21062
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.34
_cell_volume                     1286.5(3)
_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, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0769
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21062
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0593
_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)+(0.1182P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1919
_reflns_number_gt                1007
_reflns_number_total             1788
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp6061.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2ac2ab'
_cod_database_code               2206734
_cod_database_fobs_code          2206734
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_type_symbol
C1 0.5725(5) 0.5839(3) 0.2050(3) 0.0568(9) Uani d . 1 C
C2 0.5554(4) 0.6689(3) 0.1265(2) 0.0526(8) Uani d . 1 C
C3 0.6756(4) 0.6696(4) 0.0551(3) 0.0536(9) Uani d . 1 C
H3 0.6681 0.7233 0.0038 0.064 Uiso calc R 1 H
C4 0.8044(5) 0.5924(3) 0.0594(3) 0.0579(10) Uani d . 1 C
C5 0.8182(5) 0.5089(4) 0.1356(3) 0.0708(12) Uani d . 1 C
H5 0.9039 0.4557 0.1373 0.085 Uiso calc R 1 H
C6 0.7064(6) 0.5069(4) 0.2058(3) 0.0711(11) Uani d . 1 C
H6 0.7177 0.4529 0.2565 0.085 Uiso calc R 1 H
C7 0.4583(5) 0.5769(4) 0.2782(3) 0.0645(11) Uani d . 1 C
H7 0.4753 0.5225 0.3281 0.077 Uiso calc R 1 H
C8 0.2062(6) 0.6424(4) 0.3507(4) 0.0759(13) Uani d . 1 C
C9 0.0663(6) 0.7068(4) 0.3251(5) 0.0900(17) Uani d . 1 C
C10 -0.0590(9) 0.7088(6) 0.3916(5) 0.111 Uani d . 1 C
H10 -0.1543 0.7483 0.3774 0.133 Uiso calc R 1 H
C11 -0.0388(10) 0.6513(6) 0.4787(6) 0.128 Uani d . 1 C
H11 -0.1228 0.6537 0.5229 0.154 Uiso calc R 1 H
C12 0.0984(10) 0.5900(6) 0.5047(5) 0.125 Uani d . 1 C
H12 0.1068 0.5528 0.5647 0.150 Uiso calc R 1 H
C13 0.2220(8) 0.5859(5) 0.4393(4) 0.0951(17) Uani d . 1 C
H13 0.3160 0.5452 0.4544 0.114 Uiso calc R 1 H
C14 -0.0660(7) 0.8279(7) 0.2074(4) 0.111 Uani d . 1 C
H14A -0.0998 0.8796 0.2591 0.167 Uiso calc R 1 H
H14B -0.1520 0.7747 0.1905 0.167 Uiso calc R 1 H
H14C -0.0372 0.8752 0.1521 0.167 Uiso calc R 1 H
N1 0.3283(4) 0.6424(3) 0.2809(3) 0.0655(9) Uani d . 1 N
H1 0.3162 0.6920 0.2338 0.079 Uiso calc R 1 H
O1 0.4332(3) 0.7389(3) 0.12324(19) 0.0692(8) Uani d . 1 O
O2 0.9220(4) 0.5901(3) -0.0061(2) 0.0730(9) Uani d D 1 O
O3 0.0687(4) 0.7600(3) 0.2380(3) 0.084 Uani d . 1 O
H2 0.926(9) 0.655(4) -0.046(4) 0.126 Uiso d 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
C7 C1 C6 120.1(4) ?
C7 C1 C2 120.9(4) ?
C6 C1 C2 118.9(3) ?
O1 C2 C3 122.5(3) ?
O1 C2 C1 120.2(3) ?
C3 C2 C1 117.3(3) ?
C4 C3 C2 121.4(3) ?
C4 C3 H3 119.3 ?
C2 C3 H3 119.3 ?
O2 C4 C3 123.7(3) ?
O2 C4 C5 115.6(4) ?
C3 C4 C5 120.6(4) ?
C6 C5 C4 119.4(4) ?
C6 C5 H5 120.3 ?
C4 C5 H5 120.3 ?
C5 C6 C1 122.3(4) ?
C5 C6 H6 118.9 ?
C1 C6 H6 118.9 ?
N1 C7 C1 123.8(4) y
N1 C7 H7 118.1 ?
C1 C7 H7 118.1 ?
C13 C8 N1 122.6(5) y
C13 C8 C9 122.0(5) ?
N1 C8 C9 115.3(4) ?
O3 C9 C10 126.5(6) ?
O3 C9 C8 115.9(4) ?
C10 C9 C8 117.6(6) ?
C11 C10 C9 118.5(7) ?
C11 C10 H10 120.7 ?
C9 C10 H10 120.7 ?
C10 C11 C12 124.1(6) ?
C10 C11 H11 117.9 ?
C12 C11 H11 117.9 ?
C13 C12 C11 117.9(7) ?
C13 C12 H12 121.0 ?
C11 C12 H12 121.0 ?
C12 C13 C8 119.8(7) ?
C12 C13 H13 120.1 ?
C8 C13 H13 120.1 ?
O3 C14 H14A 109.5 ?
O3 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O3 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C7 N1 C8 128.4(4) y
C7 N1 H1 115.8 ?
C8 N1 H1 115.8 ?
C4 O2 H2 115(4) ?
C9 O3 C14 119.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C7 1.391(6) y
C1 C6 1.410(6) ?
C1 C2 1.448(5) ?
C2 O1 1.286(5) y
C2 C3 1.406(5) ?
C3 C4 1.379(5) ?
C3 H3 0.9300 ?
C4 O2 1.333(5) y
C4 C5 1.411(6) ?
C5 C6 1.345(6) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 N1 1.309(5) y
C7 H7 0.9300 ?
C8 C13 1.383(8) ?
C8 N1 1.401(5) y
C8 C9 1.416(7) ?
C9 O3 1.342(7) y
C9 C10 1.390(8) ?
C10 C11 1.374(10) ?
C10 H10 0.9300 ?
C11 C12 1.381(11) ?
C11 H11 0.9300 ?
C12 C13 1.371(8) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 O3 1.419(6) y
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
N1 H1 0.8600 ?
O2 H2 0.91(4) ?
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
N1 H1 O1 . 0.86 1.89 2.582(4) 137
O2 H2 O1 3_565 0.91(4) 1.60(4) 2.506(4) 175(6)
C14 H14B Cg1 1_655 0.96 2.60 3.529(7) 162
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
C7 C1 C2 O1 -0.4(6) ?
C6 C1 C2 O1 178.9(4) ?
C7 C1 C2 C3 -179.6(4) ?
C6 C1 C2 C3 -0.2(5) ?
O1 C2 C3 C4 -179.0(4) ?
C1 C2 C3 C4 0.2(5) ?
C2 C3 C4 O2 -179.5(4) ?
C2 C3 C4 C5 0.8(6) ?
O2 C4 C5 C6 178.6(4) ?
C3 C4 C5 C6 -1.6(6) ?
C4 C5 C6 C1 1.5(7) ?
C7 C1 C6 C5 178.7(4) ?
C2 C1 C6 C5 -0.6(7) ?
C6 C1 C7 N1 -177.7(4) ?
C2 C1 C7 N1 1.6(6) y
C13 C8 C9 O3 178.2(4) ?
N1 C8 C9 O3 -0.4(6) ?
C13 C8 C9 C10 -1.8(7) ?
N1 C8 C9 C10 179.6(4) ?
O3 C9 C10 C11 -178.5(5) ?
C8 C9 C10 C11 1.6(8) ?
C9 C10 C11 C12 -0.5(10) ?
C10 C11 C12 C13 -0.4(11) ?
C11 C12 C13 C8 0.1(9) ?
N1 C8 C13 C12 179.4(5) ?
C9 C8 C13 C12 1.0(8) ?
C1 C7 N1 C8 179.9(4) y
C13 C8 N1 C7 12.8(7) ?
C9 C8 N1 C7 -168.6(4) ?
C10 C9 O3 C14 1.0(7) ?
C8 C9 O3 C14 -179.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654846
