#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221717.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_2221717
loop_
_publ_author_name
'\"Ozek, Arzu'
'B\"uy\"ukg\"ung\"or, Orhan'
'Albayrak, \,Ci\(gdem'
'Odaba\,so\(glu, Mustafa'
_publ_section_title
;
 (<i>Z</i>)-6-[(5-Chloro-2-hydroxyanilino)methylene]-4-methoxycyclohexa-2,4-dienone
 0.25-hydrate
;
_journal_coeditor_code           HK2658
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1104
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H12 Cl N O3, 0.25H2 O'
_chemical_formula_moiety         'C14 H12 Cl N O3, 0.25(H2 O)'
_chemical_formula_sum            'C28 H24.5 Cl N O3.125'
_chemical_formula_weight         279.95
_chemical_name_systematic
;
(<i>Z</i>)-6-[(5-Chloro-2-hydroxyanilino)methylene]-4-methoxycyclohexa-
2,4-dienone 0.25-hydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.841(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.3670(11)
_cell_length_b                   6.7600(3)
_cell_length_c                   17.7404(9)
_cell_measurement_reflns_used    6976
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      1.96
_cell_volume                     2488.0(2)
_computing_cell_refinement       'X-RED32 (Stoe & Cie, 2002)'
_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) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_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-II'
_diffrn_measurement_method       \w
_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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6976
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1162
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.540
_exptl_crystal_size_min          0.410
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+3.3917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2352
_reflns_number_total             2588
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    hk2658.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_[local]_cod_chemical_formula_sum_orig 'C28 H24.5 Cl1 N1 O3.125'
_cod_database_code               2221717
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C C1 0.64391(7) 0.8209(2) 0.49336(8) 0.0163(3) Uani d . 1
C C2 0.63352(7) 0.6614(2) 0.43854(8) 0.0171(3) Uani d . 1
C C3 0.58193(7) 0.6836(2) 0.37118(9) 0.0191(3) Uani d . 1
H H3 0.5736 0.5834 0.3342 0.023 Uiso calc R 1
C C4 0.54480(7) 0.8493(2) 0.36036(8) 0.0189(3) Uani d . 1
H H4 0.5112 0.8593 0.3162 0.023 Uiso calc R 1
C C5 0.55578(7) 1.0069(2) 0.41439(8) 0.0175(3) Uani d . 1
C C6 0.60491(7) 0.9945(2) 0.47962(8) 0.0170(3) Uani d . 1
H H6 0.6129 1.0986 0.5149 0.020 Uiso calc R 1
C C7 0.51514(8) 1.3060(2) 0.45380(9) 0.0211(3) Uani d . 1
H H7A 0.5063 1.2434 0.4987 0.032 Uiso calc R 1
H H7B 0.4832 1.4055 0.4349 0.032 Uiso calc R 1
H H7C 0.5570 1.3663 0.4675 0.032 Uiso calc R 1
C C8 0.69160(7) 0.8057(2) 0.56359(8) 0.0164(3) Uani d . 1
H H8 0.6987 0.9125 0.5976 0.020 Uiso calc R 1
C C9 0.77299(7) 0.6029(2) 0.65047(8) 0.0158(3) Uani d . 1
C C10 0.79878(7) 0.4110(2) 0.65524(9) 0.0181(3) Uani d . 1
C C11 0.84717(7) 0.3589(2) 0.71999(9) 0.0201(3) Uani d . 1
H H11 0.8645 0.2321 0.7238 0.024 Uiso calc R 1
C C12 0.86950(7) 0.4950(2) 0.77875(8) 0.0190(3) Uani d . 1
H H12 0.9020 0.4604 0.8218 0.023 Uiso calc R 1
C C13 0.84290(7) 0.6831(2) 0.77270(8) 0.0175(3) Uani d . 1
C C14 0.79444(7) 0.7395(2) 0.70949(8) 0.0172(3) Uani d . 1
H H14 0.7767 0.8657 0.7066 0.021 Uiso calc R 1
Cl Cl1 0.873014(18) 0.85790(6) 0.84450(2) 0.02270(12) Uani d . 1
N N1 0.72613(6) 0.64456(19) 0.58204(7) 0.0165(3) Uani d . 1
H H1 0.7192 0.5522 0.5477 0.020 Uiso calc R 1
O O1 0.66836(5) 0.50302(16) 0.45048(6) 0.0219(3) Uani d . 1
O O2 0.51359(5) 1.16195(17) 0.39490(6) 0.0229(3) Uani d . 1
O O3 0.77355(5) 0.28754(18) 0.59629(7) 0.0236(3) Uani d D 1
H H3A 0.7990(11) 0.196(3) 0.5898(15) 0.055(8) Uiso d D 1
O O4 0.5000 0.3573(10) 0.2500 0.0253(14) Uani d SPD 0.25
H H4A 0.500(4) 0.286(5) 0.2880(13) 0.03(2) Uiso d PD 0.25
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0144(7) 0.0192(7) 0.0150(6) -0.0005(6) 0.0028(5) -0.0001(6)
C2 0.0154(7) 0.0190(7) 0.0166(7) 0.0000(6) 0.0033(5) -0.0010(6)
C3 0.0184(7) 0.0226(8) 0.0155(7) -0.0012(6) 0.0023(6) -0.0039(6)
C4 0.0166(7) 0.0262(8) 0.0127(7) -0.0004(6) 0.0012(5) 0.0000(6)
C5 0.0158(7) 0.0202(7) 0.0167(7) 0.0021(6) 0.0043(5) 0.0017(6)
C6 0.0173(7) 0.0187(7) 0.0147(6) 0.0001(6) 0.0037(5) -0.0016(5)
C7 0.0221(8) 0.0180(7) 0.0213(7) 0.0030(6) 0.0017(6) -0.0009(6)
C8 0.0142(7) 0.0192(7) 0.0161(7) -0.0004(6) 0.0045(5) -0.0018(6)
C9 0.0119(6) 0.0217(7) 0.0139(6) 0.0004(6) 0.0031(5) 0.0008(6)
C10 0.0165(7) 0.0194(7) 0.0180(7) 0.0003(6) 0.0031(6) -0.0021(6)
C11 0.0178(7) 0.0196(7) 0.0220(7) 0.0035(6) 0.0030(6) 0.0025(6)
C12 0.0153(7) 0.0245(8) 0.0158(7) 0.0016(6) 0.0011(5) 0.0043(6)
C13 0.0143(7) 0.0235(8) 0.0146(7) -0.0019(6) 0.0035(5) -0.0017(6)
C14 0.0158(7) 0.0183(7) 0.0166(7) 0.0018(6) 0.0021(5) 0.0009(6)
Cl1 0.0219(2) 0.0258(2) 0.01674(19) 0.00025(14) -0.00266(14) -0.00406(14)
N1 0.0151(6) 0.0184(6) 0.0142(6) 0.0007(5) 0.0001(5) -0.0018(5)
O1 0.0205(5) 0.0206(6) 0.0221(5) 0.0040(4) 0.0002(4) -0.0053(4)
O2 0.0226(6) 0.0233(6) 0.0189(5) 0.0078(4) -0.0030(4) -0.0015(4)
O3 0.0206(6) 0.0228(6) 0.0238(6) 0.0049(5) -0.0016(4) -0.0077(5)
O4 0.036(4) 0.021(3) 0.016(3) 0.000 -0.001(3) 0.000
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'
Cl Cl 0.1484 0.1585 '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
C8 C1 C6 118.69(13)
C8 C1 C2 120.36(14)
C6 C1 C2 120.91(13)
O1 C2 C3 121.57(14)
O1 C2 C1 121.51(13)
C3 C2 C1 116.90(14)
C4 C3 C2 120.85(14)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 121.89(13)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 O2 125.86(14)
C6 C5 C4 119.79(14)
O2 C5 C4 114.34(12)
C5 C6 C1 119.64(14)
C5 C6 H6 120.2
C1 C6 H6 120.2
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C1 121.66(14)
N1 C8 H8 119.2
C1 C8 H8 119.2
C14 C9 C10 120.98(13)
C14 C9 N1 123.82(13)
C10 C9 N1 115.19(13)
O3 C10 C11 124.28(14)
O3 C10 C9 116.60(13)
C11 C10 C9 119.10(14)
C12 C11 C10 120.35(14)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 119.30(13)
C13 C12 H12 120.3
C11 C12 H12 120.3
C14 C13 C12 121.88(14)
C14 C13 Cl1 118.58(12)
C12 C13 Cl1 119.49(11)
C13 C14 C9 118.37(14)
C13 C14 H14 120.8
C9 C14 H14 120.8
C8 N1 C9 128.60(13)
C8 N1 H1 115.7
C9 N1 H1 115.7
C5 O2 C7 116.07(11)
C10 O3 H3A 114.0(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.412(2)
C1 C6 1.426(2)
C1 C2 1.433(2)
C2 O1 1.2924(18)
C2 C3 1.427(2)
C3 C4 1.359(2)
C3 H3 0.9300
C4 C5 1.415(2)
C4 H4 0.9300
C5 C6 1.366(2)
C5 O2 1.3720(18)
C6 H6 0.9300
C7 O2 1.4229(19)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 N1 1.3122(19)
C8 H8 0.9300
C9 C14 1.389(2)
C9 C10 1.404(2)
C9 N1 1.4050(18)
C10 O3 1.3459(18)
C10 C11 1.395(2)
C11 C12 1.387(2)
C11 H11 0.9300
C12 C13 1.386(2)
C12 H12 0.9300
C13 C14 1.385(2)
C13 Cl1 1.7438(15)
C14 H14 0.9300
N1 H1 0.8600
O3 H3A 0.852(17)
O4 H4A 0.831(19)
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 1.84 2.5511(16) 139.5
N1 H1 O3 . 0.86 2.19 2.6063(17) 109.1
C3 H3 O4 . 0.93 2.43 3.279(5) 151.3
O4 H4A O2 1_545 0.831(19) 2.029(19) 2.842(3) 166(6)
O3 H3A O1 7_656 0.852(17) 1.743(18) 2.5652(16) 162(3)
C12 H12 O2 8_566 0.93 2.56 3.4372(18) 156.5
C7 H7A Cg1 3_565 0.96 2.834 3.644(2) 142.64
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
C8 C1 C2 O1 -2.1(2)
C6 C1 C2 O1 -179.69(14)
C8 C1 C2 C3 176.39(14)
C6 C1 C2 C3 -1.2(2)
O1 C2 C3 C4 178.48(14)
C1 C2 C3 C4 0.0(2)
C2 C3 C4 C5 0.6(2)
C3 C4 C5 C6 0.0(2)
C3 C4 C5 O2 -179.47(14)
O2 C5 C6 C1 178.19(14)
C4 C5 C6 C1 -1.2(2)
C8 C1 C6 C5 -175.82(14)
C2 C1 C6 C5 1.8(2)
C6 C1 C8 N1 175.38(14)
C2 C1 C8 N1 -2.3(2)
C14 C9 C10 O3 178.07(14)
N1 C9 C10 O3 -3.3(2)
C14 C9 C10 C11 -0.7(2)
N1 C9 C10 C11 177.86(14)
O3 C10 C11 C12 -178.82(15)
C9 C10 C11 C12 -0.1(2)
C10 C11 C12 C13 0.5(2)
C11 C12 C13 C14 0.0(2)
C11 C12 C13 Cl1 -177.44(12)
C12 C13 C14 C9 -0.9(2)
Cl1 C13 C14 C9 176.63(11)
C10 C9 C14 C13 1.2(2)
N1 C9 C14 C13 -177.27(14)
C1 C8 N1 C9 -176.94(14)
C14 C9 N1 C8 -5.5(2)
C10 C9 N1 C8 175.95(14)
C6 C5 O2 C7 -10.6(2)
C4 C5 O2 C7 168.79(13)