#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224114.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_2224114
loop_
_publ_author_name
'Şahin, Zarife Sibel'
'Gūmūş, Sūmeyye'
'Macit, Mustafa'
'Işık, Şamil'
_publ_section_title
;
 (E)-2-[(2,4-Dichlorophenyl)iminomethyl]benzene-1,4-diol
 monohydrate
;
_journal_coeditor_code           BH2254
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3022
_journal_paper_doi               10.1107/S1600536809045103
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H9 Cl2 N O2, H2 O'
_chemical_formula_moiety         'C13 H9 Cl2 N O2, H2 O'
_chemical_formula_sum            'C13 H11 Cl2 N O3'
_chemical_formula_weight         300.13
_chemical_melting_point          432
_chemical_name_systematic
;
(E)-2-[(2,4-Dichlorophenyl)iminomethyl]benzene-1,4-diol monohydrate
;
_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                 95.923(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6899(2)
_cell_length_b                   17.4289(6)
_cell_length_c                   16.1645(7)
_cell_measurement_reflns_used    12355
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      1.26
_cell_volume                     1314.23(9)
_computing_cell_refinement       'X-AREA (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)'
_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'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11982
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  0.9587
_exptl_absorpt_correction_T_min  0.8009
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.563
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0365
_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/[σ²(Fo²)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                1879
_reflns_number_total             2585
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2254.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224114
_cod_database_fobs_code          2224114
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 -0.2010(4) 0.11322(10) 0.62421(11) 0.0455(4) Uani d . 1 . .
C C2 -0.3504(4) 0.09465(12) 0.54787(12) 0.0540(5) Uani d . 1 . .
H H2A -0.3024 0.0502 0.5207 0.065 Uiso calc R 1 . .
C C3 -0.5665(4) 0.14033(12) 0.51181(12) 0.0556(5) Uani d . 1 . .
C C4 -0.6388(4) 0.20661(11) 0.55258(13) 0.0554(5) Uani d . 1 . .
H H4 -0.7851 0.2380 0.5287 0.066 Uiso calc R 1 . .
C C5 -0.4951(5) 0.22589(11) 0.62805(13) 0.0573(5) Uani d . 1 . .
H H5 -0.5461 0.2702 0.6550 0.069 Uiso calc R 1 . .
C C6 -0.2748(4) 0.18020(11) 0.66461(12) 0.0510(4) Uani d . 1 . .
C C7 0.0230(4) 0.06279(11) 0.66080(12) 0.0485(4) Uani d . 1 . .
H H7 0.0640 0.0180 0.6331 0.058 Uiso calc R 1 . .
C C8 0.3792(4) 0.03047(10) 0.76835(11) 0.0467(4) Uani d . 1 . .
C C9 0.4933(4) 0.04822(11) 0.84932(12) 0.0512(4) Uani d . 1 . .
C C10 0.7030(4) 0.00366(12) 0.89192(13) 0.0560(5) Uani d . 1 . .
H H11 0.7748 0.0162 0.9460 0.067 Uiso calc R 1 . .
C C11 0.8040(4) -0.05934(11) 0.85325(12) 0.0518(5) Uani d . 1 . .
C C12 0.7014(4) -0.07811(11) 0.77313(12) 0.0547(5) Uani d . 1 . .
H H12 0.7737 -0.1205 0.7473 0.066 Uiso calc R 1 . .
C C13 0.4907(4) -0.03366(11) 0.73152(12) 0.0522(5) Uani d . 1 . .
H H13 0.4209 -0.0467 0.6774 0.063 Uiso calc R 1 . .
N N1 0.1649(3) 0.07852(9) 0.73022(9) 0.0492(4) Uani d . 1 . .
O O1 -0.6995(5) 0.11940(12) 0.43607(10) 0.0909(6) Uani d . 1 . .
H H1 -0.848(8) 0.148(2) 0.420(2) 0.121(12) Uiso d . 1 . .
O O2 -0.1365(4) 0.20076(10) 0.73902(10) 0.0729(5) Uani d . 1 . .
H H2 -0.007(7) 0.166(2) 0.751(2) 0.105(10) Uiso d . 1 . .
O O3 -1.1524(5) 0.19928(14) 0.37204(14) 0.0930(7) Uani d . 1 . .
H H1O -1.167(7) 0.232(2) 0.333(2) 0.112(11) Uiso d . 1 . .
H H2O -1.317(10) 0.200(3) 0.385(3) 0.154(17) Uiso d . 1 . .
Cl Cl1 1.06563(11) -0.11630(3) 0.90637(4) 0.06643(18) Uani d . 1 . .
Cl Cl2 0.36487(14) 0.12696(4) 0.89962(4) 0.0773(2) Uani 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
C2 C1 C6 . . 118.80(17) ?
C2 C1 C7 . . 119.88(16) ?
C6 C1 C7 . . 121.32(17) ?
C3 C2 C1 . . 121.61(18) ?
C3 C2 H2A . . 119.2 ?
C1 C2 H2A . . 119.2 ?
O1 C3 C2 . . 118.39(18) ?
O1 C3 C4 . . 122.44(19) ?
C2 C3 C4 . . 119.16(19) ?
C5 C4 C3 . . 120.22(19) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.91(18) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
O2 C6 C5 . . 119.58(18) ?
O2 C6 C1 . . 121.12(18) ?
C5 C6 C1 . . 119.30(18) ?
N1 C7 C1 . . 121.34(17) ?
N1 C7 H7 . . 119.3 ?
C1 C7 H7 . . 119.3 ?
C13 C8 C9 . . 116.98(18) ?
C13 C8 N1 . . 125.12(17) ?
C9 C8 N1 . . 117.89(16) ?
C10 C9 C8 . . 121.82(18) ?
C10 C9 Cl2 . . 118.39(16) ?
C8 C9 Cl2 . . 119.78(15) ?
C11 C10 C9 . . 119.00(19) ?
C11 C10 H11 . . 120.5 ?
C9 C10 H11 . . 120.5 ?
C10 C11 C12 . . 121.10(19) ?
C10 C11 Cl1 . . 119.48(16) ?
C12 C11 Cl1 . . 119.42(16) ?
C11 C12 C13 . . 119.40(18) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C12 C13 C8 . . 121.69(18) ?
C12 C13 H13 . . 119.2 ?
C8 C13 H13 . . 119.2 ?
C7 N1 C8 . . 122.99(16) ?
C3 O1 H1 . . 113(2) ?
C6 O2 H2 . . 106(2) ?
H1O O3 H2O . . 100(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 . 1.393(3) ?
C1 C6 . 1.398(3) ?
C1 C7 . 1.448(3) ?
C2 C3 . 1.371(3) ?
C2 H2A . 0.9300 ?
C3 O1 . 1.365(3) ?
C3 C4 . 1.389(3) ?
C4 C5 . 1.373(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9300 ?
C6 O2 . 1.354(2) y
C7 N1 . 1.274(2) y
C7 H7 . 0.9300 ?
C8 C13 . 1.393(3) ?
C8 C9 . 1.397(3) ?
C8 N1 . 1.401(2) y
C9 C10 . 1.380(3) ?
C9 Cl2 . 1.734(2) y
C10 C11 . 1.372(3) ?
C10 H11 . 0.9300 ?
C11 C12 . 1.374(3) ?
C11 Cl1 . 1.735(2) y
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
O1 H1 . 0.87(4) ?
O2 H2 . 0.87(4) ?
O3 H1O . 0.85(4) ?
O3 H2O . 0.82(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
_geom_hbond_publ_flag
O3 H1O O2 4_465 0.85(4) 1.94(4) 2.774(3) 170(3) yes
O2 H2 N1 . 0.87(4) 1.77(3) 2.569(2) 152(3) yes
O3 H2O O1 1_455 0.82(4) 2.49(5) 3.184(3) 143(4) yes
O1 H1 O3 . 0.87(4) 1.79(4) 2.659(3) 171(3) yes
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
C6 C1 C2 C3 . . . . 0.0(3) ?
C7 C1 C2 C3 . . . . 179.05(17) ?
C1 C2 C3 O1 . . . . 178.63(19) ?
C1 C2 C3 C4 . . . . -0.2(3) ?
O1 C3 C4 C5 . . . . -178.8(2) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . 0.5(3) ?
C4 C5 C6 O2 . . . . 179.88(19) ?
C4 C5 C6 C1 . . . . -0.7(3) ?
C2 C1 C6 O2 . . . . 179.87(18) ?
C7 C1 C6 O2 . . . . 0.8(3) ?
C2 C1 C6 C5 . . . . 0.5(3) ?
C7 C1 C6 C5 . . . . -178.58(18) ?
C2 C1 C7 N1 . . . . 179.43(17) ?
C6 C1 C7 N1 . . . . -1.5(3) ?
C13 C8 C9 C10 . . . . -1.2(3) ?
N1 C8 C9 C10 . . . . 179.39(17) ?
C13 C8 C9 Cl2 . . . . -179.77(14) ?
N1 C8 C9 Cl2 . . . . 0.9(2) ?
C8 C9 C10 C11 . . . . 0.7(3) ?
Cl2 C9 C10 C11 . . . . 179.20(15) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C9 C10 C11 Cl1 . . . . -179.49(14) ?
C10 C11 C12 C13 . . . . -1.0(3) ?
Cl1 C11 C12 C13 . . . . 178.96(15) ?
C11 C12 C13 C8 . . . . 0.4(3) ?
C9 C8 C13 C12 . . . . 0.7(3) ?
N1 C8 C13 C12 . . . . -179.98(17) ?
C1 C7 N1 C8 . . . . 178.71(16) ?
C13 C8 N1 C7 . . . . 9.2(3) ?
C9 C8 N1 C7 . . . . -171.48(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000850
