# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_18042_Naghmana
_database_code_depnum_ccdc_archive 'CCDC 2108057'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nadeem Arshad'
;King Abdulaziz University
Saudi Arabia
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'N-[2-(2,4-Dihydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamidemethanol solvate'
_chemical_name_common            
'N-[2-(2,4-Dihydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamidemethanol solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 N3 O5'
_chemical_formula_sum            'C22 H21 N3 O5'
_chemical_formula_weight         407.42

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6661(9)
_cell_length_b                   11.0426(8)
_cell_length_c                   12.2572(12)
_cell_angle_alpha                108.672(7)
_cell_angle_beta                 102.099(8)
_cell_angle_gamma                108.033(8)
_cell_volume                     992.66(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1847
_cell_measurement_theta_min      3.2064
_cell_measurement_theta_max      29.1220

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 96)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7704
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.213
_diffrn_reflns_theta_max         29.186
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4628
_reflns_number_gt                2882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.2413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4628
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045

