#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222993.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_2222993
loop_
_publ_author_name
'Özek, Arzu'
'Albayrak, Çiğdem'
'Büyükgüngör, Orhan'
_publ_section_title
(Z)-6-[(5-Chloro-2-hydroxyphenyl)aminomethylene]-2-ethoxycyclohexa-2,4-dienone
_journal_coeditor_code           BT5027
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2153
_journal_paper_doi               10.1107/S1600536809031298
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C15 H14 Cl N O3'
_chemical_formula_sum            'C15 H14 Cl N O3'
_chemical_formula_weight         291.72
_chemical_name_systematic
;(Z)-6-[(5-Chloro-2-hydroxyphenyl)aminomethylene]-2-ethoxycyclohexa-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.168(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4313(7)
_cell_length_b                   7.1710(2)
_cell_length_c                   12.6071(6)
_cell_measurement_reflns_used    15989
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.8
_cell_volume                     1300.94(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_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 II diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15989
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.9269
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0405
_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)+(0.0546P)²+0.0402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2084
_reflns_number_total             2680
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5027.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222993
_cod_database_fobs_code          2222993
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
C C1 0.42045(11) 0.1210(2) 0.12588(13) 0.0348(3) Uani d . 1 . .
C C2 0.35762(11) 0.0951(2) 0.18490(13) 0.0347(3) Uani d . 1 . .
C C3 0.25975(11) 0.0968(2) 0.11617(14) 0.0354(4) Uani d . 1 . .
C C4 0.23136(12) 0.1153(2) 0.00038(14) 0.0405(4) Uani d . 1 . .
C C5 0.29497(13) 0.1391(3) -0.05529(15) 0.0420(4) Uani d . 1 . .
C C6 0.38735(12) 0.1431(2) 0.00582(14) 0.0397(4) Uani d . 1 . .
C C7 0.10537(12) 0.1023(3) 0.11398(16) 0.0429(4) Uani d . 1 . .
C C8 0.05590(13) 0.1030(4) 0.19698(19) 0.0515(5) Uani d . 1 . .
C C9 0.51704(11) 0.1302(2) 0.18651(15) 0.0372(4) Uani d . 1 . .
C C10 0.65028(11) 0.1159(2) 0.36438(14) 0.0349(3) Uani d . 1 . .
C C11 0.67292(11) 0.1056(2) 0.48215(14) 0.0366(4) Uani d . 1 . .
C C12 0.76552(12) 0.0967(3) 0.55291(16) 0.0435(4) Uani d . 1 . .
C C13 0.83466(12) 0.0983(3) 0.50765(16) 0.0446(4) Uani d . 1 . .
C C14 0.81081(11) 0.1101(2) 0.39143(16) 0.0398(4) Uani d . 1 . .
C C15 0.71950(12) 0.1205(2) 0.31875(15) 0.0385(4) Uani d . 1 . .
N N1 0.55488(9) 0.1157(2) 0.29736(12) 0.0375(3) Uani d . 1 . .
O O1 0.38649(8) 0.07391(19) 0.29284(10) 0.0458(3) Uani d . 1 . .
O O2 0.20269(8) 0.08261(18) 0.17686(10) 0.0432(3) Uani d . 1 . .
O O3 0.60157(9) 0.10408(19) 0.52038(11) 0.0462(3) Uani d . 1 . .
Cl Cl1 0.89826(3) 0.10870(7) 0.33413(5) 0.05476(17) Uani d . 1 . .
H H1 0.5154(16) 0.095(3) 0.3294(19) 0.057(6) Uiso d . 1 . .
H H3 0.6156(16) 0.048(3) 0.584(2) 0.058(6) Uiso d . 1 . .
H H4 0.1662(17) 0.112(3) -0.044(2) 0.067(7) Uiso d . 1 . .
H H5 0.2700(13) 0.157(3) -0.1342(18) 0.048(5) Uiso d . 1 . .
H H6 0.4309(14) 0.169(3) -0.0299(16) 0.047(5) Uiso d . 1 . .
H H7A 0.0925(14) 0.221(3) 0.0713(18) 0.055(6) Uiso d . 1 . .
H H7B 0.0851(14) -0.005(3) 0.0600(18) 0.049(5) Uiso d . 1 . .
H H8A 0.0771(17) 0.197(3) 0.250(2) 0.067(7) Uiso d . 1 . .
H H8B 0.0646(15) -0.015(4) 0.2363(19) 0.063(6) Uiso d . 1 . .
H H8C -0.0076(18) 0.120(3) 0.157(2) 0.068(7) Uiso d . 1 . .
H H9 0.5538(13) 0.150(2) 0.1399(16) 0.041(5) Uiso d . 1 . .
H H12 0.7798(15) 0.087(3) 0.633(2) 0.055(6) Uiso d . 1 . .
H H13 0.8974(15) 0.090(3) 0.5585(18) 0.053(6) Uiso d . 1 . .
H H15 0.7051(13) 0.124(3) 0.2410(18) 0.046(5) Uiso d . 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
C9 C1 C6 . . 118.39(15) ?
C9 C1 C2 . . 120.41(15) ?
C6 C1 C2 . . 121.18(14) ?
O1 C2 C1 . . 121.83(14) ?
O1 C2 C3 . . 121.77(14) ?
C1 C2 C3 . . 116.40(14) ?
O2 C3 C4 . . 125.61(15) ?
O2 C3 C2 . . 114.20(14) ?
C4 C3 C2 . . 120.18(15) ?
C3 C4 C5 . . 122.02(16) ?
C3 C4 H4 . . 118.9(14) ?
C5 C4 H4 . . 119.0(14) ?
C6 C5 C4 . . 119.94(16) ?
C6 C5 H5 . . 123.1(12) ?
C4 C5 H5 . . 116.9(12) ?
C5 C6 C1 . . 120.23(16) ?
C5 C6 H6 . . 120.8(12) ?
C1 C6 H6 . . 118.8(12) ?
O2 C7 C8 . . 108.09(15) ?
O2 C7 H7A . . 110.6(12) ?
C8 C7 H7A . . 108.8(12) ?
O2 C7 H7B . . 108.1(12) ?
C8 C7 H7B . . 111.4(12) ?
H7A C7 H7B . . 109.8(17) ?
C7 C8 H8A . . 111.7(15) ?
C7 C8 H8B . . 110.1(14) ?
H8A C8 H8B . . 109(2) ?
C7 C8 H8C . . 109.0(15) ?
H8A C8 H8C . . 109(2) ?
H8B C8 H8C . . 108.4(19) ?
N1 C9 C1 . . 123.47(15) ?
N1 C9 H9 . . 121.9(11) ?
C1 C9 H9 . . 114.6(11) ?
C15 C10 C11 . . 120.52(15) ?
C15 C10 N1 . . 123.16(15) ?
C11 C10 N1 . . 116.29(14) ?
O3 C11 C12 . . 123.59(16) ?
O3 C11 C10 . . 117.09(15) ?
C12 C11 C10 . . 119.32(15) ?
C13 C12 C11 . . 120.32(17) ?
C13 C12 H12 . . 121.3(13) ?
C11 C12 H12 . . 118.4(13) ?
C14 C13 C12 . . 119.38(16) ?
C14 C13 H13 . . 122.5(13) ?
C12 C13 H13 . . 118.1(13) ?
C15 C14 C13 . . 121.78(16) ?
C15 C14 Cl1 . . 118.87(14) ?
C13 C14 Cl1 . . 119.34(13) ?
C14 C15 C10 . . 118.66(16) ?
C14 C15 H15 . . 120.2(12) ?
C10 C15 H15 . . 121.0(12) ?
C9 N1 C10 . . 127.35(15) ?
C9 N1 H1 . . 113.4(15) ?
C10 N1 H1 . . 119.0(15) ?
C3 O2 C7 . . 116.33(13) ?
C11 O3 H3 . . 112.0(16) ?
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 C9 . 1.410(2) ?
C1 C6 . 1.421(2) ?
C1 C2 . 1.432(2) ?
C2 O1 . 1.279(2) ?
C2 C3 . 1.445(2) ?
C3 O2 . 1.363(2) ?
C3 C4 . 1.371(2) ?
C4 C5 . 1.408(3) ?
C4 H4 . 0.96(2) ?
C5 C6 . 1.354(2) ?
C5 H5 . 0.94(2) ?
C6 H6 . 0.95(2) ?
C7 O2 . 1.430(2) ?
C7 C8 . 1.502(3) ?
C7 H7A . 0.99(2) ?
C7 H7B . 1.00(2) ?
C8 H8A . 0.92(2) ?
C8 H8B . 0.97(2) ?
C8 H8C . 0.93(3) ?
C9 N1 . 1.310(2) ?
C9 H9 . 0.96(2) ?
C10 C15 . 1.384(2) ?
C10 C11 . 1.399(2) ?
C10 N1 . 1.408(2) ?
C11 O3 . 1.3519(19) ?
C11 C12 . 1.386(2) ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.95(2) ?
C13 C14 . 1.378(3) ?
C13 H13 . 0.95(2) ?
C14 C15 . 1.378(2) ?
C14 Cl1 . 1.7456(17) ?
C15 H15 . 0.92(2) ?
N1 H1 . 0.86(2) ?
O3 H3 . 0.85(2) ?
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(2) 1.88(2) 2.5957(17) 140(2)
N1 H1 O3 . 0.86(2) 2.29(2) 2.640(2) 104.3(17)
O3 H3 O1 3_656 0.85(2) 1.79(2) 2.6258(17) 165(2)
C9 H9 O3 4_565 0.96(2) 2.594(19) 3.419(2) 143.8(14)
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
C9 C1 C2 O1 . . . . -2.2(3) ?
C6 C1 C2 O1 . . . . 179.60(16) ?
C9 C1 C2 C3 . . . . 176.96(15) ?
C6 C1 C2 C3 . . . . -1.3(2) ?
O1 C2 C3 O2 . . . . 2.8(2) ?
C1 C2 C3 O2 . . . . -176.34(14) ?
O1 C2 C3 C4 . . . . -178.42(16) ?
C1 C2 C3 C4 . . . . 2.5(2) ?
O2 C3 C4 C5 . . . . 176.54(16) ?
C2 C3 C4 C5 . . . . -2.1(3) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C4 C5 C6 C1 . . . . 0.8(3) ?
C9 C1 C6 C5 . . . . -178.59(17) ?
C2 C1 C6 C5 . . . . -0.3(3) ?
C6 C1 C9 N1 . . . . 178.49(16) ?
C2 C1 C9 N1 . . . . 0.2(3) ?
C15 C10 C11 O3 . . . . 179.17(15) ?
N1 C10 C11 O3 . . . . -2.6(2) ?
C15 C10 C11 C12 . . . . -1.1(3) ?
N1 C10 C11 C12 . . . . 177.13(16) ?
O3 C11 C12 C13 . . . . 179.80(17) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
C12 C13 C14 C15 . . . . 0.0(3) ?
C12 C13 C14 Cl1 . . . . -179.07(14) ?
C13 C14 C15 C10 . . . . -1.0(3) ?
Cl1 C14 C15 C10 . . . . 178.08(13) ?
C11 C10 C15 C14 . . . . 1.5(3) ?
N1 C10 C15 C14 . . . . -176.58(16) ?
C1 C9 N1 C10 . . . . 177.28(17) ?
C15 C10 N1 C9 . . . . -4.2(3) ?
C11 C10 N1 C9 . . . . 177.63(17) ?
C4 C3 O2 C7 . . . . -4.7(2) ?
C2 C3 O2 C7 . . . . 174.00(15) ?
C8 C7 O2 C3 . . . . -174.00(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655856
