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#$Date: 2022-04-28 11:53:28 +0300 (Thu, 28 Apr 2022) $
#$Revision: 274740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105076.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_8105076
loop_
_publ_author_name
'Lo, Kong Mun'
'Lee, See Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Redetermination of the crystal structure of
 N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide
 monohydrate, C16H17FN2O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              259
_journal_page_last               261
_journal_paper_doi               10.1515/ncrs-2019-0568
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C16 H15 F N2 O3, H2 O'
_chemical_formula_sum            'C16 H17 F N2 O4'
_chemical_formula_weight         320.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.3830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.23280(10)
_cell_length_b                   12.9330(2)
_cell_length_c                   12.3477(2)
_cell_measurement_reflns_used    8143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4410
_cell_measurement_theta_min      4.8230
_cell_volume                     1462.19(4)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2017/4 [3]'
_computing_structure_refinement  'SHELXL-2017/4 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.049
_diffrn_reflns_theta_min         4.830
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0538P)²+0.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2353
_reflns_number_total             2601
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0568_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105076
_shelx_shelxl_version_number     2014/7
_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_min   0.885
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_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_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
F1 F 0.17356(8) 0.75207(6) 1.22153(6) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.43989(11) 0.94056(7) 0.82362(7) 0.0251(2) Uani 1 1 d . . . . .
O2 O 0.70132(10) 0.91296(7) 0.56094(7) 0.0211(2) Uani 1 1 d . . . . .
H2O H 0.651(2) 0.9037(16) 0.6122(16) 0.042(5) Uiso 1 1 d . . . . .
O3 O 0.86944(10) 0.91781(7) 0.40723(7) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.51705(11) 0.77511(9) 0.80658(8) 0.0182(2) Uani 1 1 d . . . . .
H1N H 0.5191(18) 0.7126(15) 0.8264(13) 0.029(4) Uiso 1 1 d . . . . .
N2 N 0.58967(11) 0.79844(9) 0.71832(8) 0.0191(2) Uani 1 1 d . . . . .
C1 C 0.44589(13) 0.85001(10) 0.85485(9) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.37537(13) 0.81800(10) 0.95217(9) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.33094(13) 0.71721(10) 0.97067(9) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.3456(16) 0.6637(12) 0.9204(12) 0.019(3) Uiso 1 1 d . . . . .
C4 C 0.26254(13) 0.69411(10) 1.06164(10) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.2337(18) 0.6235(14) 1.0741(12) 0.027(4) Uiso 1 1 d . . . . .
C5 C 0.24076(13) 0.77353(10) 1.13235(9) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.28506(14) 0.87364(10) 1.11818(10) 0.0206(3) Uani 1 1 d . . . . .
H6 H 0.2698(17) 0.9256(13) 1.1721(12) 0.024(4) Uiso 1 1 d . . . . .
C7 C 0.35205(14) 0.89561(10) 1.02650(10) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.3833(17) 0.9652(13) 1.0161(12) 0.023(4) Uiso 1 1 d . . . . .
C8 C 0.65234(13) 0.72022(10) 0.68004(10) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.6457(17) 0.6521(13) 0.7102(12) 0.022(4) Uiso 1 1 d . . . . .
C9 C 0.73890(13) 0.72823(10) 0.58954(9) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.76169(13) 0.82141(10) 0.53635(9) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.85275(13) 0.82294(10) 0.45288(9) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.91745(14) 0.73239(10) 0.42304(10) 0.0203(3) Uani 1 1 d . . . . .
H12 H 0.9816(19) 0.7337(13) 0.3685(14) 0.030(4) Uiso 1 1 d . . . . .
C13 C 0.89223(14) 0.63949(10) 0.47478(10) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.9351(17) 0.5769(13) 0.4534(12) 0.022(4) Uiso 1 1 d . . . . .
C14 C 0.80462(14) 0.63723(10) 0.55698(10) 0.0213(3) Uani 1 1 d . . . . .
H14 H 0.7899(17) 0.5719(13) 0.5950(12) 0.025(4) Uiso 1 1 d . . . . .
C15 C 0.97702(14) 0.92450(10) 0.33209(10) 0.0201(3) Uani 1 1 d . . . . .
H15A H 0.9538(16) 0.8763(12) 0.2733(12) 0.020(3) Uiso 1 1 d . . . . .
H15B H 1.0717(17) 0.9103(12) 0.3719(12) 0.021(4) Uiso 1 1 d . . . . .
C16 C 0.97373(15) 1.03313(11) 0.28903(11) 0.0236(3) Uani 1 1 d . . . . .
H16A H 0.8793(18) 1.0508(12) 0.2475(13) 0.025(4) Uiso 1 1 d . . . . .
H16B H 1.0481(19) 1.0381(14) 0.2387(14) 0.036(4) Uiso 1 1 d . . . . .
H16C H 0.9957(18) 1.0839(13) 0.3498(13) 0.029(4) Uiso 1 1 d . . . . .
O1W O 0.51710(10) 0.55211(7) 0.85542(8) 0.0224(2) Uani 1 1 d . . . . .
H1W H 0.581(2) 0.5425(14) 0.9103(16) 0.034(5) Uiso 1 1 d . . . . .
H2W H 0.535(2) 0.5086(19) 0.8022(18) 0.059(6) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C10 O2 H2O 109.0(14) . .
C11 O3 C15 116.19(9) . .
C1 N1 N2 120.21(11) . .
C1 N1 H1N 123.5(11) . .
N2 N1 H1N 116.3(11) . .
C8 N2 N1 113.86(11) . .
O1 C1 N1 123.25(11) . .
O1 C1 C2 120.50(11) . .
N1 C1 C2 116.24(11) . .
C3 C2 C7 119.42(11) . .
C3 C2 C1 123.89(11) . .
C7 C2 C1 116.68(11) . .
C4 C3 C2 120.47(12) . .
C4 C3 H3 119.2(9) . .
C2 C3 H3 120.3(9) . .
C5 C4 C3 118.02(12) . .
C5 C4 H4 122.4(9) . .
C3 C4 H4 119.6(9) . .
F1 C5 C6 117.97(11) . .
F1 C5 C4 118.64(11) . .
C6 C5 C4 123.39(11) . .
C5 C6 C7 117.87(12) . .
C5 C6 H6 119.6(9) . .
C7 C6 H6 122.6(9) . .
C6 C7 C2 120.80(12) . .
C6 C7 H7 118.3(9) . .
C2 C7 H7 120.9(9) . .
N2 C8 C9 122.87(12) . .
N2 C8 H8 121.7(9) . .
C9 C8 H8 115.5(9) . .
C10 C9 C14 119.31(11) . .
C10 C9 C8 123.38(12) . .
C14 C9 C8 117.30(11) . .
O2 C10 C9 123.63(11) . .
O2 C10 C11 116.78(11) . .
C9 C10 C11 119.59(11) . .
O3 C11 C12 124.99(11) . .
O3 C11 C10 115.02(11) . .
C12 C11 C10 119.99(11) . .
C11 C12 C13 120.22(11) . .
C11 C12 H12 120.1(10) . .
C13 C12 H12 119.7(10) . .
C14 C13 C12 120.30(12) . .
C14 C13 H13 119.3(9) . .
C12 C13 H13 120.4(9) . .
C13 C14 C9 120.58(12) . .
C13 C14 H14 120.0(9) . .
C9 C14 H14 119.4(9) . .
O3 C15 C16 107.39(10) . .
O3 C15 H15A 110.0(9) . .
C16 C15 H15A 110.3(9) . .
O3 C15 H15B 108.3(8) . .
C16 C15 H15B 109.5(9) . .
H15A C15 H15B 111.2(13) . .
C15 C16 H16A 112.3(9) . .
C15 C16 H16B 107.5(11) . .
H16A C16 H16B 107.5(14) . .
C15 C16 H16C 110.9(9) . .
H16A C16 H16C 108.7(13) . .
H16B C16 H16C 109.9(14) . .
H1W O1W H2W 108.5(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.3602(13) .
O1 C1 1.2320(16) .
O2 C10 1.3596(15) .
O2 H2O 0.84(2) .
O3 C11 1.3671(15) .
O3 C15 1.4463(14) .
N1 C1 1.3512(17) .
N1 N2 1.3842(14) .
N1 H1N 0.84(2) .
N2 C8 1.2852(17) .
C1 C2 1.4968(16) .
C2 C3 1.3942(19) .
C2 C7 1.3953(18) .
C3 C4 1.3900(17) .
C3 H3 0.951(16) .
C4 C5 1.3795(18) .
C4 H4 0.969(18) .
C5 C6 1.3757(19) .
C6 C7 1.3874(17) .
C6 H6 0.969(16) .
C7 H7 0.959(17) .
C8 C9 1.4587(16) .
C8 H8 0.961(17) .
C9 C10 1.4011(18) .
C9 C14 1.4064(19) .
C10 C11 1.4114(16) .
C11 C12 1.3858(18) .
C12 C13 1.3943(18) .
C12 H12 0.952(17) .
C13 C14 1.3770(18) .
C13 H13 0.954(16) .
C14 H14 0.984(17) .
C15 C16 1.5011(19) .
C15 H15A 0.960(16) .
C15 H15B 0.964(16) .
C16 H16A 0.980(17) .
C16 H16B 0.986(17) .
C16 H16C 0.998(17) .
O1W H1W 0.85(2) .
O1W H2W 0.90(2) .
