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#$Date: 2023-06-08 11:14:56 +0300 (Thu, 08 Jun 2023) $
#$Revision: 284407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107315.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107315
loop_
_publ_author_name
'Liu, Kun'
'Han, Qiang'
'Zhao, Kai-Hui'
'Zhong, Qi-Di'
'Zhang, Zhi-Fei'
_publ_section_title
;
 Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-
 hydroxybenzohydrazide-water (1/1), C14H13Cl1N2O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1135
_journal_page_last               1136
_journal_paper_doi               10.1515/ncrs-2022-0246
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H11 Cl N2 O3, H2 O'
_chemical_formula_sum            'C14 H13 Cl N2 O4'
_chemical_formula_weight         308.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 97.47(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.257(5)
_cell_length_b                   16.161(4)
_cell_length_c                   13.262(3)
_cell_measurement_reflns_used    1240
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      21.696
_cell_measurement_theta_min      2.521
_cell_volume                     2817.2(14)
_computing_cell_refinement       'APEX2-2008 [1]'
_computing_data_collection       'APEX2-2008 [1]'
_computing_data_reduction        'SAINT- 2008 [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         3.098
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008 [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1556
_reflns_number_total             2878
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0246_suppl.cif
_cod_data_source_block           1
_cod_database_code               8107315
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 H1-H4A
 2.3 with sigma of 0.02
3.a Riding coordinates:
 O4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), N1(H1)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0735(2) 0.35609(18) 0.8730(2) 0.0442(7) Uani 1 1 d . . . . .
C2 C -0.03652(19) 0.37122(17) 0.8694(2) 0.0407(7) Uani 1 1 d . . . . .
C3 C -0.1108(2) 0.31042(18) 0.8521(2) 0.0537(8) Uani 1 1 d . . . . .
H3 H -0.091723 0.255873 0.842667 0.064 Uiso 1 1 calc R U . . .
C4 C -0.2121(2) 0.32979(19) 0.8486(3) 0.0575(9) Uani 1 1 d . . . . .
H4 H -0.260960 0.288477 0.836163 0.069 Uiso 1 1 calc R U . . .
C5 C -0.2414(2) 0.40943(18) 0.8635(2) 0.0470(7) Uani 1 1 d . . . . .
C6 C -0.1695(2) 0.47048(18) 0.8828(2) 0.0552(9) Uani 1 1 d . . . . .
H6 H -0.189080 0.524572 0.894287 0.066 Uiso 1 1 calc R U . . .
C7 C -0.0686(2) 0.45094(18) 0.8852(2) 0.0509(8) Uani 1 1 d . . . . .
H7 H -0.020218 0.492648 0.897713 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2390(2) 0.18814(18) 0.8735(2) 0.0457(7) Uani 1 1 d . . . . .
H8 H 0.193614 0.143976 0.866715 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3484(2) 0.17369(18) 0.8846(2) 0.0445(7) Uani 1 1 d . . . . .
C10 C 0.4179(2) 0.2395(2) 0.8921(2) 0.0493(7) Uani 1 1 d . . . . .
C11 C 0.5213(2) 0.2252(2) 0.9048(2) 0.0607(9) Uani 1 1 d . . . . .
H11 H 0.566435 0.269490 0.910864 0.073 Uiso 1 1 calc R U . . .
C12 C 0.5576(3) 0.1460(3) 0.9085(3) 0.0716(10) Uani 1 1 d . . . . .
H12 H 0.627445 0.137072 0.917060 0.086 Uiso 1 1 calc R U . . .
C13 C 0.4926(3) 0.0791(2) 0.8998(3) 0.0677(10) Uani 1 1 d . . . . .
H13 H 0.517799 0.025378 0.901489 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3896(2) 0.0937(2) 0.8885(2) 0.0547(8) Uani 1 1 d . . . . .
Cl1 Cl 0.30838(7) 0.00874(5) 0.87773(8) 0.0805(4) Uani 1 1 d . . . . .
N1 N 0.10424(17) 0.27646(14) 0.86669(17) 0.0461(6) Uani 1 1 d . . . . .
H1 H 0.061068 0.236513 0.858806 0.055 Uiso 1 1 calc DR U . . .
N2 N 0.20666(16) 0.26212(15) 0.87335(17) 0.0434(6) Uani 1 1 d . . . . .
O1 O -0.34286(13) 0.42525(13) 0.85927(19) 0.0621(7) Uani 1 1 d . . . . .
H1A H -0.351628 0.475006 0.866598 0.093 Uiso 1 1 calc R U . . .
O2 O 0.13688(14) 0.41191(12) 0.88265(17) 0.0591(6) Uani 1 1 d . . . . .
O3 O 0.38714(15) 0.31897(13) 0.88702(17) 0.0599(6) Uani 1 1 d . . . . .
H3A H 0.325734 0.321064 0.889667 0.090 Uiso 1 1 calc R U . . .
O4 O 0.01026(17) 0.12368(14) 0.7914(2) 0.0852(8) Uani 1 1 d . . . . .
H4A H -0.050427 0.112224 0.766364 0.128 Uiso 1 1 d DR U . . .
H4B H 0.039603 0.136584 0.740334 0.128 Uiso 1 1 d R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 117.4(2) . .
O2 C1 C2 122.8(3) . .
O2 C1 N1 119.8(3) . .
C3 C2 C1 124.4(3) . .
C7 C2 C1 118.2(2) . .
C7 C2 C3 117.4(2) . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.9(3) . .
C4 C3 H3 119.6 . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.3(3) . .
C5 C4 H4 119.8 . .
C4 C5 C6 120.1(3) . .
O1 C5 C4 117.9(3) . .
O1 C5 C6 122.0(3) . .
C5 C6 H6 120.3 . .
C7 C6 C5 119.4(3) . .
C7 C6 H6 120.3 . .
C2 C7 H7 119.0 . .
C6 C7 C2 122.0(3) . .
C6 C7 H7 119.0 . .
C9 C8 H8 120.6 . .
N2 C8 H8 120.6 . .
N2 C8 C9 118.8(3) . .
C10 C9 C8 121.5(3) . .
C14 C9 C8 122.0(3) . .
C14 C9 C10 116.5(3) . .
C11 C10 C9 121.0(3) . .
O3 C10 C9 121.8(3) . .
O3 C10 C11 117.1(3) . .
C10 C11 H11 120.0 . .
C12 C11 C10 120.1(3) . .
C12 C11 H11 120.0 . .
C11 C12 H12 119.4 . .
C11 C12 C13 121.3(3) . .
C13 C12 H12 119.4 . .
C12 C13 H13 120.8 . .
C14 C13 C12 118.4(3) . .
C14 C13 H13 120.8 . .
C9 C14 Cl1 119.4(2) . .
C13 C14 C9 122.6(3) . .
C13 C14 Cl1 118.0(3) . .
C1 N1 H1 121.3 . .
C1 N1 N2 117.4(2) . .
N2 N1 H1 121.3 . .
C8 N2 N1 119.4(2) . .
C5 O1 H1A 109.5 . .
C10 O3 H3A 109.5 . .
H4A O4 H4B 104.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.474(4) .
C1 N1 1.356(3) .
C1 O2 1.228(3) .
C2 C3 1.389(4) .
C2 C7 1.381(4) .
C3 H3 0.9300 .
C3 C4 1.374(4) .
C4 H4 0.9300 .
C4 C5 1.366(4) .
C5 C6 1.372(4) .
C5 O1 1.364(3) .
C6 H6 0.9300 .
C6 C7 1.371(4) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C8 C9 1.457(4) .
C8 N2 1.270(3) .
C9 C10 1.402(4) .
C9 C14 1.402(4) .
C10 C11 1.379(4) .
C10 O3 1.347(4) .
C11 H11 0.9300 .
C11 C12 1.365(5) .
C12 H12 0.9300 .
C12 C13 1.378(5) .
C13 H13 0.9300 .
C13 C14 1.374(4) .
C14 Cl1 1.739(3) .
N1 H1 0.8600 .
N1 N2 1.369(3) .
O1 H1A 0.8200 .
O3 H3A 0.8200 .
O4 H4A 0.8500 .
O4 H4B 0.8498 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O2 0.93 2.51 3.194(3) 130.4 6_565 yes
C8 H8 O4 0.93 2.53 3.256(4) 135.6 . yes
N1 H1 O4 0.86 2.10 2.885(3) 150.9 . yes
O1 H1A O2 0.82 1.85 2.667(3) 176.5 6_565 yes
O3 H3A N2 0.82 1.83 2.547(3) 144.9 . yes
O4 H4A O1 0.85 2.13 2.897(3) 150.1 7_456 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 -179.2(3) . . . .
C1 C2 C7 C6 179.8(3) . . . .
C1 N1 N2 C8 176.1(3) . . . .
C2 C1 N1 N2 -177.9(2) . . . .
C2 C3 C4 C5 -0.8(5) . . . .
C3 C2 C7 C6 -0.7(4) . . . .
C3 C4 C5 C6 -0.6(5) . . . .
C3 C4 C5 O1 180.0(3) . . . .
C4 C5 C6 C7 1.2(5) . . . .
C5 C6 C7 C2 -0.6(5) . . . .
C7 C2 C3 C4 1.4(4) . . . .
C8 C9 C10 C11 178.5(3) . . . .
C8 C9 C10 O3 -1.6(4) . . . .
C8 C9 C14 C13 -179.4(3) . . . .
C8 C9 C14 Cl1 1.1(4) . . . .
C9 C8 N2 N1 -177.7(2) . . . .
C9 C10 C11 C12 1.2(5) . . . .
C10 C9 C14 C13 0.5(4) . . . .
C10 C9 C14 Cl1 -179.0(2) . . . .
C10 C11 C12 C13 0.0(5) . . . .
C11 C12 C13 C14 -0.8(5) . . . .
C12 C13 C14 C9 0.6(5) . . . .
C12 C13 C14 Cl1 -179.9(3) . . . .
C14 C9 C10 C11 -1.4(4) . . . .
C14 C9 C10 O3 178.5(3) . . . .
N1 C1 C2 C3 -5.3(4) . . . .
N1 C1 C2 C7 174.1(3) . . . .
N2 C8 C9 C10 -1.8(4) . . . .
N2 C8 C9 C14 178.1(3) . . . .
O1 C5 C6 C7 -179.4(3) . . . .
O2 C1 C2 C3 175.7(3) . . . .
O2 C1 C2 C7 -4.9(4) . . . .
O2 C1 N1 N2 1.1(4) . . . .
O3 C10 C11 C12 -178.7(3) . . . .
