#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/70/2207028.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_2207028
loop_
_publ_author_name
'Özek, Arzu'
'Yüce, Süheyla'
'Albayrak, Çiğdem'
'Odabaşoğlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2-Hydroxy-6-[(1-napthylamino)methylene]cyclohexa-2,4-dien-1-one
;
_journal_coeditor_code           OB6563
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3179
_journal_page_last               o3181
_journal_paper_doi               10.1107/S1600536805027546
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H13 N O2'
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_name_systematic
;
2-Hydroxy-6-[(1-napthylamino)methylene]cyclohexa-2,4-dien-1-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 108.738(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3546(5)
_cell_length_b                   23.7901(17)
_cell_length_c                   7.4919(5)
_cell_measurement_reflns_used    11212
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      1.71
_cell_volume                     1241.36(15)
_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      100
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11951
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0458
_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)+(0.0602P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                1668
_reflns_number_total             2435
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6563.cif
_cod_data_source_block           I
_cod_original_cell_volume        1241.35(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207028
_cod_database_fobs_code          2207028
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_type_symbol
C1 0.3656(3) 0.50975(8) 0.2339(3) 0.0241(4) Uani d . 1 C
C2 0.4898(3) 0.46940(7) 0.1997(3) 0.0243(4) Uani d . 1 C
C3 0.6931(3) 0.47626(7) 0.2757(2) 0.0236(4) Uani d . 1 C
C4 0.8087(3) 0.43510(8) 0.2239(2) 0.0250(4) Uani d . 1 C
C5 0.7277(3) 0.39035(8) 0.1123(3) 0.0268(4) Uani d . 1 C
C6 0.5266(3) 0.38369(8) 0.0411(3) 0.0275(4) Uani d . 1 C
C7 0.4103(3) 0.42222(8) 0.0831(3) 0.0263(4) Uani d . 1 C
C8 0.3211(3) 0.60023(8) 0.3694(2) 0.0244(4) Uani d . 1 C
C9 0.1240(3) 0.60006(8) 0.3004(3) 0.0289(4) Uani d . 1 C
C10 0.0190(3) 0.64574(8) 0.3363(3) 0.0309(5) Uani d . 1 C
C11 0.1118(3) 0.69048(9) 0.4410(3) 0.0311(5) Uani d . 1 C
C12 0.3145(3) 0.69158(8) 0.5164(3) 0.0267(4) Uani d . 1 C
C13 0.4130(3) 0.73688(8) 0.6298(3) 0.0306(5) Uani d . 1 C
C14 0.6078(3) 0.73732(8) 0.7035(3) 0.0306(5) Uani d . 1 C
C15 0.7163(3) 0.69277(8) 0.6661(3) 0.0291(4) Uani d . 1 C
C16 0.6266(3) 0.64809(8) 0.5569(3) 0.0269(4) Uani d . 1 C
C17 0.4240(3) 0.64604(8) 0.4794(2) 0.0248(4) Uani d . 1 C
N1 0.4310(2) 0.55513(6) 0.3355(2) 0.0242(4) Uani d . 1 N
O1 0.77225(19) 0.51768(5) 0.38424(18) 0.0277(3) Uani d . 1 O
O2 1.0043(2) 0.44126(6) 0.28678(19) 0.0301(3) Uani d D 1 O
H1 0.225(3) 0.5059(9) 0.173(3) 0.033(6) Uiso d . 1 H
H2 1.038(4) 0.4627(9) 0.387(3) 0.047 Uiso d D 1 H
H3 0.575(4) 0.5570(11) 0.383(3) 0.050(7) Uiso d . 1 H
H5 0.814(3) 0.3624(10) 0.086(3) 0.038(6) Uiso d . 1 H
H6 0.475(3) 0.3512(9) -0.037(3) 0.028(5) Uiso d . 1 H
H7 0.268(3) 0.4190(9) 0.032(3) 0.029(5) Uiso d . 1 H
H9 0.056(3) 0.5679(10) 0.223(3) 0.039(6) Uiso d . 1 H
H10 -0.127(4) 0.6463(9) 0.283(3) 0.038(6) Uiso d . 1 H
H11 0.039(3) 0.7212(10) 0.473(3) 0.039(6) Uiso d . 1 H
H13 0.337(3) 0.7664(9) 0.655(3) 0.028(5) Uiso d . 1 H
H14 0.676(4) 0.7696(10) 0.786(3) 0.048(7) Uiso d . 1 H
H15 0.861(4) 0.6934(10) 0.724(3) 0.040(6) Uiso d . 1 H
H16 0.707(3) 0.6190(9) 0.534(3) 0.031(5) 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
N1 C1 C2 121.77(18) y
N1 C1 H1 118.1(12) ?
C2 C1 H1 120.0(12) ?
C1 C2 C7 119.15(18) y
C1 C2 C3 120.57(17) y
C7 C2 C3 120.25(17) ?
O1 C3 C2 122.70(17) y
O1 C3 C4 120.45(17) y
C2 C3 C4 116.85(16) ?
C5 C4 O2 119.79(17) no
C5 C4 C3 121.28(17) ?
O2 C4 C3 118.93(16) no
C4 C5 C6 121.14(18) ?
C4 C5 H5 118.0(14) ?
C6 C5 H5 120.9(14) ?
C7 C6 C5 119.89(18) ?
C7 C6 H6 121.8(13) ?
C5 C6 H6 118.3(13) ?
C6 C7 C2 120.56(18) ?
C6 C7 H7 121.5(12) ?
C2 C7 H7 117.9(12) ?
C9 C8 N1 121.67(18) no
C9 C8 C17 121.28(18) ?
N1 C8 C17 117.05(17) no
C8 C9 C10 120.20(19) ?
C8 C9 H9 119.6(14) ?
C10 C9 H9 120.2(14) ?
C11 C10 C9 120.5(2) ?
C11 C10 H10 118.9(13) ?
C9 C10 H10 120.6(13) ?
C10 C11 C12 120.74(19) ?
C10 C11 H11 120.8(14) ?
C12 C11 H11 118.3(14) ?
C11 C12 C13 121.56(18) ?
C11 C12 C17 119.72(18) ?
C13 C12 C17 118.73(18) ?
C14 C13 C12 121.19(19) ?
C14 C13 H13 121.3(13) ?
C12 C13 H13 117.4(13) ?
C13 C14 C15 120.26(19) ?
C13 C14 H14 120.2(14) ?
C15 C14 H14 119.5(14) ?
C16 C15 C14 120.4(2) ?
C16 C15 H15 120.3(13) ?
C14 C15 H15 119.3(13) ?
C15 C16 C17 120.82(19) ?
C15 C16 H16 117.2(14) ?
C17 C16 H16 122.0(13) ?
C16 C17 C8 123.80(17) ?
C16 C17 C12 118.59(17) ?
C8 C17 C12 117.58(17) ?
C1 N1 C8 126.91(17) y
C1 N1 H3 113.0(15) ?
C8 N1 H3 120.0(15) ?
C4 O2 H2 109.3(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.320(2) y
C1 C2 1.404(3) y
C1 H1 0.99(2) ?
C2 C7 1.427(3) y
C2 C3 1.429(3) y
C3 O1 1.291(2) y
C3 C4 1.429(3) y
C4 C5 1.367(3) yes
C4 O2 1.370(2) y
C5 C6 1.411(3) yes
C5 H5 0.98(2) ?
C6 C7 1.357(3) yes
C6 H6 0.97(2) ?
C7 H7 1.00(2) ?
C8 C9 1.374(3) ?
C8 N1 1.415(2) y
C8 C17 1.428(3) no
C9 C10 1.408(3) ?
C9 H9 0.99(2) ?
C10 C11 1.367(3) no
C10 H10 1.02(2) ?
C11 C12 1.415(3) ?
C11 H11 0.98(2) ?
C12 C13 1.419(3) ?
C12 C17 1.430(3) no
C13 C14 1.360(3) ?
C13 H13 0.95(2) ?
C14 C15 1.408(3) no
C14 H14 1.01(3) ?
C15 C16 1.374(3) ?
C15 H15 1.01(3) ?
C16 C17 1.415(3) ?
C16 H16 0.96(2) ?
N1 H3 1.00(3) no
O2 H2 0.876(17) ?
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 H3 O1 . 1.00(3) 1.73(3) 2.576(2) 140(2)
O2 H2 O1 3_766 0.88(2) 1.89(2) 2.670(2) 148(2)
C13 H13 Cg1 4_554 0.95(2) 3.12(2) 4.008(2) 155(2)
C13 H13 Cg2 4_554 0.95(2) 3.26(2) 3.705(2) 111(2)
C14 H14 Cg2 4_554 1.01(3) 3.03(3) 3.604(2) 117(2)
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
N1 C1 C2 C7 -177.77(17) y
N1 C1 C2 C3 0.2(3) y
C1 C2 C3 O1 3.1(3) y
C7 C2 C3 O1 -178.91(16) ?
C1 C2 C3 C4 -176.07(16) ?
C7 C2 C3 C4 1.9(3) ?
O1 C3 C4 C5 178.65(17) ?
C2 C3 C4 C5 -2.2(3) ?
O1 C3 C4 O2 -1.9(2) no
C2 C3 C4 O2 177.23(16) no
O2 C4 C5 C6 -178.22(16) ?
C3 C4 C5 C6 1.2(3) ?
C4 C5 C6 C7 0.1(3) ?
C5 C6 C7 C2 -0.3(3) ?
C1 C2 C7 C6 177.30(17) ?
C3 C2 C7 C6 -0.7(3) ?
N1 C8 C9 C10 -179.80(17) no
C17 C8 C9 C10 0.4(3) ?
C8 C9 C10 C11 -0.4(3) ?
C9 C10 C11 C12 -0.5(3) ?
C10 C11 C12 C13 -178.21(18) ?
C10 C11 C12 C17 1.4(3) ?
C11 C12 C13 C14 179.27(18) ?
C17 C12 C13 C14 -0.4(3) ?
C12 C13 C14 C15 0.9(3) ?
C13 C14 C15 C16 -0.9(3) ?
C14 C15 C16 C17 0.3(3) ?
C15 C16 C17 C8 -178.12(18) ?
C15 C16 C17 C12 0.2(3) ?
C9 C8 C17 C16 178.84(17) ?
N1 C8 C17 C16 -1.0(3) y
C9 C8 C17 C12 0.5(3) ?
N1 C8 C17 C12 -179.30(15) ?
C11 C12 C17 C16 -179.83(17) ?
C13 C12 C17 C16 -0.2(2) ?
C11 C12 C17 C8 -1.4(2) ?
C13 C12 C17 C8 178.25(17) ?
C2 C1 N1 C8 175.65(16) y
C9 C8 N1 C1 2.2(3) y
C17 C8 N1 C1 -177.96(17) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654859
