#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:56:20 +0300 (Thu, 05 May 2022) $
#$Revision: 275071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244115.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_7244115
loop_
_publ_author_name
'Kausar, Naghmana'
'Murtaza, Shahzad'
'Arshad, Muhammad Nadeem'
'Zaib Saleem, Rahman Shah'
'Asiri, Abdullah M.'
'Kausar, Samia'
'Altaf, Ataf Ali'
'Tatheer, Adina'
'Elnaggar, Ashraf Y.'
'El-Bahy, Salah M'
_publ_section_title
;
 Design, synthesis, crystal structure, in vitro cytotoxicity
 evaluation, density functional theory calculations and docking studies of
 2-(benzamido) benzohydrazide derivatives as potent AChE and BChE
 inhibitors.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              154
_journal_page_last               167
_journal_paper_doi               10.1039/d1ra07221h
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C22 H21 N3 O5'
_chemical_formula_sum            'C22 H21 N3 O5'
_chemical_formula_weight         407.42
_chemical_name_common
'N-[2-(2,4-Dihydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamidemethanol solvate'
_chemical_name_systematic
'N-[2-(2,4-Dihydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamidemethanol solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                108.672(7)
_cell_angle_beta                 102.099(8)
_cell_angle_gamma                108.033(8)
_cell_formula_units_Z            2
_cell_length_a                   8.6661(9)
_cell_length_b                   11.0426(8)
_cell_length_c                   12.2572(12)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.1220
_cell_measurement_theta_min      3.2064
_cell_volume                     992.66(19)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7704
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.186
_diffrn_reflns_theta_min         3.213
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 96)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0560
_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)+(0.0517P)²+0.2413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2882
_reflns_number_total             4628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra07221h2.cif
_cod_data_source_block           18042_Naghmana
_cod_depositor_comments          'Adding full bibliography for 7244115.cif.'
_cod_original_cell_volume        992.66(17)
_cod_database_code               7244115
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.7686(3) 0.9620(2) 0.91476(17) 0.0362(5) Uani 1 1 d . . . . .
C2 C 0.8475(3) 0.9223(2) 0.82807(17) 0.0359(5) Uani 1 1 d . . . . .
C3 C 0.9308(3) 1.0194(2) 0.78839(19) 0.0444(5) Uani 1 1 d . . . . .
H3 H 0.981589 0.993609 0.730104 0.053 Uiso 1 1 calc R U . . .
C4 C 0.9399(3) 1.1543(2) 0.8337(2) 0.0528(6) Uani 1 1 d . . . . .
H4 H 0.996291 1.218636 0.806181 0.063 Uiso 1 1 calc R U . . .
C5 C 0.8647(3) 1.1925(2) 0.9201(2) 0.0516(6) Uani 1 1 d . . . . .
H5 H 0.871662 1.283396 0.951611 0.062 Uiso 1 1 calc R U . . .
C6 C 0.7800(3) 1.0981(2) 0.9601(2) 0.0463(6) Uani 1 1 d . . . . .
H6 H 0.729526 1.125317 1.018191 0.056 Uiso 1 1 calc R U . . .
C7 C 0.6390(3) 0.8801(2) 1.05438(18) 0.0378(5) Uani 1 1 d . . . . .
C8 C 0.5233(3) 0.7514(2) 1.05787(18) 0.0376(5) Uani 1 1 d . . . . .
C9 C 0.4037(3) 0.6375(2) 0.95240(19) 0.0459(6) Uani 1 1 d . . . . .
H9 H 0.398493 0.638943 0.876290 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2930(4) 0.5227(2) 0.9589(2) 0.0571(7) Uani 1 1 d . . . . .
H10 H 0.212928 0.447052 0.887315 0.068 Uiso 1 1 calc R U . . .
C11 C 0.2996(4) 0.5188(3) 1.0705(2) 0.0577(7) Uani 1 1 d . . . . .
H11 H 0.224021 0.441069 1.074847 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4187(4) 0.6305(3) 1.1758(2) 0.0565(7) Uani 1 1 d . . . . .
H12 H 0.424709 0.627544 1.251477 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5294(3) 0.7469(2) 1.1703(2) 0.0480(6) Uani 1 1 d . . . . .
H13 H 0.608381 0.822702 1.242109 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8372(3) 0.7769(2) 0.77769(17) 0.0361(5) Uani 1 1 d . . . . .
C15 C 1.1182(3) 0.6374(2) 0.67801(18) 0.0417(5) Uani 1 1 d . . . . .
H15 H 1.203302 0.720775 0.689328 0.050 Uiso 1 1 calc R U . . .
C16 C 1.1417(3) 0.5099(2) 0.63182(17) 0.0386(5) Uani 1 1 d . . . . .
C17 C 1.0197(3) 0.3801(2) 0.61329(18) 0.0413(5) Uani 1 1 d . . . . .
C18 C 1.0489(3) 0.2599(2) 0.57260(19) 0.0473(6) Uani 1 1 d . . . . .
H18 H 0.967493 0.174696 0.560966 0.057 Uiso 1 1 calc R U . . .
C19 C 1.2010(3) 0.2675(2) 0.54920(18) 0.0452(6) Uani 1 1 d . . . . .
C20 C 1.3217(3) 0.3939(3) 0.5639(2) 0.0487(6) Uani 1 1 d . . . . .
H20 H 1.421812 0.398178 0.545862 0.058 Uiso 1 1 calc R U . . .
C21 C 1.2911(3) 0.5119(2) 0.60516(19) 0.0449(5) Uani 1 1 d . . . . .
H21 H 1.372833 0.596513 0.615841 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4660(5) 0.9318(4) 0.6179(3) 0.0749(9) Uani 1 1 d . . . . .
N1 N 0.6758(2) 0.86084(17) 0.94968(15) 0.0409(4) Uani 1 1 d . . . . .
H1N H 0.637225 0.775337 0.897650 0.049 Uiso 1 1 calc R U . . .
N2 N 0.9762(2) 0.76771(17) 0.74899(14) 0.0392(4) Uani 1 1 d . . . . .
H2N H 1.059716 0.841654 0.758829 0.047 Uiso 1 1 calc R U . . .
N3 N 0.9836(2) 0.63938(17) 0.70391(14) 0.0393(4) Uani 1 1 d . . . . .
O1 O 0.6953(2) 0.99476(15) 1.14100(13) 0.0508(4) Uani 1 1 d . . . . .
O2 O 0.7142(2) 0.67424(15) 0.76343(14) 0.0483(4) Uani 1 1 d . . . . .
O3 O 0.8699(2) 0.36956(18) 0.63652(16) 0.0570(5) Uani 1 1 d . . . . .
O4 O 1.2251(3) 0.14709(17) 0.51257(17) 0.0623(5) Uani 1 1 d . . . . .
H2O H 1.316244 0.161904 0.498775 0.093 Uiso 1 1 calc R U . . .
O5 O 0.4712(3) 0.8190(2) 0.5275(2) 0.0817(7) Uani 1 1 d . . . . .
H3O H 0.374643 0.770981 0.475593 0.123 Uiso 1 1 calc R U . . .
H22A H 0.457(5) 0.905(4) 0.683(4) 0.123 Uiso 1 1 d . U . . .
H22B H 0.571(6) 1.013(4) 0.644(3) 0.123 Uiso 1 1 d . U . . .
H22C H 0.362(5) 0.945(4) 0.591(3) 0.123 Uiso 1 1 d . U . . .
H1O H 0.874(4) 0.464(3) 0.669(3) 0.096(10) 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 0.0033 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'
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
_geom_angle_publ_flag
C6 C1 N1 122.06(19) . . ?
C6 C1 C2 119.2(2) . . ?
N1 C1 C2 118.68(16) . . ?
C3 C2 C1 118.84(17) . . ?
C3 C2 C14 120.69(18) . . ?
C1 C2 C14 120.45(18) . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.64(19) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 N1 123.4(2) . . ?
O1 C7 C8 121.47(18) . . ?
N1 C7 C8 115.09(17) . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 C7 119.1(2) . . ?
C9 C8 C7 122.09(19) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O2 C14 N2 122.47(18) . . ?
O2 C14 C2 123.50(19) . . ?
N2 C14 C2 114.03(19) . . ?
N3 C15 C16 121.7(2) . . ?
N3 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C21 C16 C17 117.46(19) . . ?
C21 C16 C15 120.1(2) . . ?
C17 C16 C15 122.5(2) . . ?
O3 C17 C18 118.1(2) . . ?
O3 C17 C16 120.86(18) . . ?
C18 C17 C16 121.0(2) . . ?
C17 C18 C19 119.5(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
O4 C19 C20 122.4(2) . . ?
O4 C19 C18 117.0(2) . . ?
C20 C19 C18 120.6(2) . . ?
C21 C20 C19 119.0(2) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C16 122.4(2) . . ?
C20 C21 H21 118.8 . . ?
C16 C21 H21 118.8 . . ?
O5 C22 H22A 106(2) . . ?
O5 C22 H22B 109(2) . . ?
H22A C22 H22B 111(3) . . ?
O5 C22 H22C 111(2) . . ?
H22A C22 H22C 105(3) . . ?
H22B C22 H22C 115(3) . . ?
C7 N1 C1 128.60(17) . . ?
C7 N1 H1N 115.7 . . ?
C1 N1 H1N 115.7 . . ?
C14 N2 N3 119.55(18) . . ?
C14 N2 H2N 120.2 . . ?
N3 N2 H2N 120.2 . . ?
C15 N3 N2 116.58(19) . . ?
C17 O3 H1O 106.9(19) . . ?
C19 O4 H2O 109.5 . . ?
C22 O5 H3O 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.388(3) . ?
C1 N1 1.404(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.382(3) . ?
C2 C14 1.490(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.228(2) . ?
C7 N1 1.354(2) . ?
C7 C8 1.484(3) . ?
C8 C13 1.384(3) . ?
C8 C9 1.385(3) . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O2 1.224(3) . ?
C14 N2 1.348(3) . ?
C15 N3 1.276(3) . ?
C15 C16 1.436(3) . ?
C15 H15 0.9300 . ?
C16 C21 1.395(3) . ?
C16 C17 1.406(3) . ?
C17 O3 1.365(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.390(3) . ?
C18 H18 0.9300 . ?
C19 O4 1.357(2) . ?
C19 C20 1.389(3) . ?
C20 C21 1.369(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O5 1.397(3) . ?
C22 H22A 0.95(4) . ?
C22 H22B 0.96(4) . ?
C22 H22C 0.96(4) . ?
N1 H1N 0.8600 . ?
N2 N3 1.374(2) . ?
N2 H2N 0.8600 . ?
O3 H1O 0.97(3) . ?
O4 H2O 0.8200 . ?
O5 H3O 0.8200 . ?
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
C6 H6 O1 0.93 2.40 2.923(3) 115.7 .
N1 H1N O2 0.86 2.04 2.702(2) 133.6 .
N2 H2N O1 0.86 2.10 2.882(2) 151.8 2_777
O4 H2O O5 0.82 1.90 2.712(3) 173.8 2_766
O5 H3O O3 0.82 2.04 2.852(3) 169.9 2_666
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.5(3) . . . . ?
N1 C1 C2 C3 176.44(19) . . . . ?
C6 C1 C2 C14 -179.92(19) . . . . ?
N1 C1 C2 C14 -2.0(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C14 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
N1 C1 C6 C5 -177.0(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
O1 C7 C8 C13 -24.7(3) . . . . ?
N1 C7 C8 C13 155.54(19) . . . . ?
O1 C7 C8 C9 152.3(2) . . . . ?
N1 C7 C8 C9 -27.4(3) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -176.9(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C8 -1.0(4) . . . . ?
C9 C8 C13 C12 0.4(3) . . . . ?
C7 C8 C13 C12 177.6(2) . . . . ?
C3 C2 C14 O2 -146.8(2) . . . . ?
C1 C2 C14 O2 31.6(3) . . . . ?
C3 C2 C14 N2 33.3(3) . . . . ?
C1 C2 C14 N2 -148.28(19) . . . . ?
N3 C15 C16 C21 -179.63(19) . . . . ?
N3 C15 C16 C17 -0.6(3) . . . . ?
C21 C16 C17 O3 -179.55(19) . . . . ?
C15 C16 C17 O3 1.3(3) . . . . ?
C21 C16 C17 C18 1.3(3) . . . . ?
C15 C16 C17 C18 -177.80(18) . . . . ?
O3 C17 C18 C19 -179.42(19) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 O4 178.30(19) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
O4 C19 C20 C21 -177.77(19) . . . . ?
C18 C19 C20 C21 1.9(3) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
C15 C16 C21 C20 178.35(19) . . . . ?
O1 C7 N1 C1 -5.4(4) . . . . ?
C8 C7 N1 C1 174.35(19) . . . . ?
C6 C1 N1 C7 -25.9(3) . . . . ?
C2 C1 N1 C7 156.2(2) . . . . ?
O2 C14 N2 N3 -1.1(3) . . . . ?
C2 C14 N2 N3 178.73(16) . . . . ?
C16 C15 N3 N2 179.15(17) . . . . ?
C14 N2 N3 C15 179.73(18) . . . . ?
