# 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. 
# 
#######################################################################

data_VMI-40
_database_code_depnum_ccdc_archive 'CCDC 2132092'
loop_
_audit_author_name
_audit_author_address
'Goran Bogdanovic'
;Vinca Institute of Nuclear Science, University of Belgrade
Serbia
;
_audit_update_record             
;
2022-01-03 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
4-((4-hydroxy-3-methoxyphenyl)(3-hydroxy-5-methyl-1H-pyrazol-4-yl)methyl)-5-methyl-1,2-dihydro-3H-pyrazol-3-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 O4'
_chemical_formula_sum            'C16 H18 N4 O4'
_chemical_formula_weight         330.34

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      Orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n 21 a'
_space_group_name_Hall           'P -2ac -2n'

_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+1/2, -z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, y, -z+1/2'

_cell_length_a                   14.9633(3)
_cell_length_b                   12.6206(2)
_cell_length_c                   8.60670(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1625.34(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12203
_cell_measurement_theta_min      2.1240
_cell_measurement_theta_max      26.3710

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent intense orange'
_exptl_absorpt_correction_T_min  0.98635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.968
_oxdiff_exptl_absorpt_empirical_full_max 1.046
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_reflns_number            25332
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3334
_reflns_number_gt                3048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.1342P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3334
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
H1N1 H 0.177(3) -0.159(3) -0.170(4) 0.078(11) Uiso 1 1 d . . . . .
H1N2 H 0.084(3) -0.107(3) -0.383(5) 0.092(12) Uiso 1 1 d . . . . .
H1N4 H -0.272(2) -0.085(3) 0.308(4) 0.075(9) Uiso 1 1 d . . . . .
H1O2 H 0.050(3) -0.121(4) 0.252(5) 0.116(14) Uiso 1 1 d . . . . .
H1O4 H 0.173(3) 0.341(3) 0.448(4) 0.081(11) Uiso 1 1 d . . . . .
O1 O 0.11721(10) -0.13243(16) 0.1020(2) 0.0552(4) Uani 1 1 d . . . . .
O2 O 0.00740(12) -0.1182(2) 0.3321(2) 0.0664(6) Uani 1 1 d . . . . .
O3 O 0.24596(11) 0.25325(16) 0.0943(2) 0.0618(5) Uani 1 1 d . . . . .
O4 O 0.19531(12) 0.32429(18) 0.3640(3) 0.0674(6) Uani 1 1 d . . . . .
N1 N 0.12250(16) -0.1387(2) -0.1655(3) 0.0600(6) Uani 1 1 d . . . . .
N2 N 0.08546(16) -0.08309(19) -0.2862(3) 0.0612(6) Uani 1 1 d . . . . .
N3 N -0.14585(13) -0.1196(2) 0.3523(2) 0.0572(6) Uani 1 1 d . . . . .
N4 N -0.21395(13) -0.07423(18) 0.2730(2) 0.0539(5) Uani 1 1 d . . . . .
C1 C -0.03225(13) 0.03737(18) 0.0432(2) 0.0364(4) Uani 1 1 d . . . . .
H1 H -0.0710 0.0824 -0.0206 0.044 Uiso 1 1 calc R U . . .
C2 C 0.01960(14) -0.02979(18) -0.0690(2) 0.0384(4) Uani 1 1 d . . . . .
C3 C 0.08808(13) -0.10336(18) -0.0294(3) 0.0438(5) Uani 1 1 d . . . . .
C4 C 0.01881(16) -0.0222(2) -0.2270(3) 0.0481(5) Uani 1 1 d . . . . .
C5 C -0.0390(2) 0.0417(3) -0.3308(3) 0.0753(9) Uani 1 1 d . . . . .
H5A H -0.0339 0.1152 -0.3036 0.113 Uiso 1 1 calc R U . . .
H5B H -0.1000 0.0194 -0.3193 0.113 Uiso 1 1 calc R U . . .
H5C H -0.0205 0.0319 -0.4366 0.113 Uiso 1 1 calc R U . . .
C6 C -0.09384(13) -0.02346(18) 0.1487(2) 0.0383(4) Uani 1 1 d . . . . .
C7 C -0.07302(14) -0.08854(19) 0.2772(3) 0.0478(5) Uani 1 1 d . . . . .
C8 C -0.18559(14) -0.01733(19) 0.1511(2) 0.0431(5) Uani 1 1 d . . . . .
C9 C -0.24882(17) 0.0373(3) 0.0443(3) 0.0624(7) Uani 1 1 d . . . . .
H9A H -0.3082 0.0336 0.0863 0.094 Uiso 1 1 calc R U . . .
H9B H -0.2476 0.0033 -0.0555 0.094 Uiso 1 1 calc R U . . .
H9C H -0.2315 0.1101 0.0332 0.094 Uiso 1 1 calc R U . . .
C10 C 0.02919(14) 0.11344(17) 0.1326(2) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.10963(15) 0.14735(18) 0.0685(2) 0.0417(5) Uani 1 1 d . . . . .
H11 H 0.1270 0.1221 -0.0285 0.050 Uiso 1 1 calc R U . . .
C12 C 0.16408(15) 0.21770(18) 0.1463(3) 0.0442(5) Uani 1 1 d . . . . .
C13 C 0.13873(14) 0.25694(19) 0.2905(3) 0.0468(5) Uani 1 1 d . . . . .
C14 C 0.05852(15) 0.2243(2) 0.3542(3) 0.0491(6) Uani 1 1 d . . . . .
H14 H 0.0409 0.2500 0.4507 0.059 Uiso 1 1 calc R U . . .
C15 C 0.00421(14) 0.15337(19) 0.2754(2) 0.0435(5) Uani 1 1 d . . . . .
H15 H -0.0498 0.1325 0.3193 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2794(2) 0.2073(3) -0.0433(4) 0.0733(9) Uani 1 1 d . . . . .
H16A H 0.2393 0.2222 -0.1277 0.110 Uiso 1 1 calc R U . . .
H16B H 0.2844 0.1320 -0.0299 0.110 Uiso 1 1 calc R U . . .
H16C H 0.3372 0.2364 -0.0661 0.110 Uiso 1 1 calc R U . . .


_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
O1 C3 1.267(3) . ?
O2 C7 1.346(3) . ?
O2 H1O2 0.94(5) . ?
O3 C12 1.379(3) . ?
O3 C16 1.410(3) . ?
O4 C13 1.356(3) . ?
O4 H1O4 0.82(4) . ?
N1 C3 1.355(3) . ?
N1 N2 1.371(4) . ?
N1 H1N1 0.85(4) . ?
N2 C4 1.358(3) . ?
N2 H1N2 0.89(4) . ?
N3 C7 1.327(3) . ?
N3 N4 1.354(3) . ?
N4 C8 1.340(3) . ?
N4 H1N4 0.93(3) . ?
C1 C2 1.501(3) . ?
C1 C6 1.504(3) . ?
C1 C10 1.536(3) . ?
C1 H1 0.9800 . ?
C2 C4 1.364(3) . ?
C2 C3 1.424(3) . ?
C4 C5 1.481(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C8 1.375(3) . ?
C6 C7 1.412(3) . ?
C8 C9 1.489(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.380(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C7 O2 H1O2 111(3) . . ?
C12 O3 C16 116.99(19) . . ?
C13 O4 H1O4 108(3) . . ?
C3 N1 N2 109.4(2) . . ?
C3 N1 H1N1 120(2) . . ?
N2 N1 H1N1 120(2) . . ?
C4 N2 N1 107.6(2) . . ?
C4 N2 H1N2 122(3) . . ?
N1 N2 H1N2 123(3) . . ?
C7 N3 N4 104.31(18) . . ?
C8 N4 N3 112.54(18) . . ?
C8 N4 H1N4 129(2) . . ?
N3 N4 H1N4 119(2) . . ?
C2 C1 C6 114.63(18) . . ?
C2 C1 C10 111.46(16) . . ?
C6 C1 C10 112.57(15) . . ?
C2 C1 H1 105.8 . . ?
C6 C1 H1 105.8 . . ?
C10 C1 H1 105.8 . . ?
C4 C2 C3 106.9(2) . . ?
C4 C2 C1 126.7(2) . . ?
C3 C2 C1 125.90(19) . . ?
O1 C3 N1 123.1(2) . . ?
O1 C3 C2 130.5(2) . . ?
N1 C3 C2 106.3(2) . . ?
N2 C4 C2 109.1(2) . . ?
N2 C4 C5 120.7(2) . . ?
C2 C4 C5 130.1(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C7 103.95(18) . . ?
C8 C6 C1 126.31(19) . . ?
C7 C6 C1 129.35(18) . . ?
N3 C7 O2 118.7(2) . . ?
N3 C7 C6 111.87(19) . . ?
O2 C7 C6 129.4(2) . . ?
N4 C8 C6 107.33(19) . . ?
N4 C8 C9 122.0(2) . . ?
C6 C8 C9 130.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.4(2) . . ?
C15 C10 C1 120.81(18) . . ?
C11 C10 C1 120.76(17) . . ?
C12 C11 C10 121.10(19) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 O3 125.2(2) . . ?
C11 C12 C13 120.2(2) . . ?
O3 C12 C13 114.62(19) . . ?
O4 C13 C14 123.0(2) . . ?
O4 C13 C12 118.0(2) . . ?
C14 C13 C12 119.0(2) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.8(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C3 N1 N2 C4 -7.9(3) . . . . ?
C7 N3 N4 C8 0.6(3) . . . . ?
C6 C1 C2 C4 121.7(2) . . . . ?
C10 C1 C2 C4 -108.9(2) . . . . ?
C6 C1 C2 C3 -67.6(3) . . . . ?
C10 C1 C2 C3 61.7(3) . . . . ?
N2 N1 C3 O1 -172.1(2) . . . . ?
N2 N1 C3 C2 6.1(3) . . . . ?
C4 C2 C3 O1 176.0(2) . . . . ?
C1 C2 C3 O1 3.8(4) . . . . ?
C4 C2 C3 N1 -2.1(2) . . . . ?
C1 C2 C3 N1 -174.3(2) . . . . ?
N1 N2 C4 C2 6.5(3) . . . . ?
N1 N2 C4 C5 -175.4(2) . . . . ?
C3 C2 C4 N2 -2.8(3) . . . . ?
C1 C2 C4 N2 169.3(2) . . . . ?
C3 C2 C4 C5 179.4(3) . . . . ?
C1 C2 C4 C5 -8.5(4) . . . . ?
C2 C1 C6 C8 -115.1(2) . . . . ?
C10 C1 C6 C8 116.1(2) . . . . ?
C2 C1 C6 C7 73.2(3) . . . . ?
C10 C1 C6 C7 -55.5(3) . . . . ?
N4 N3 C7 O2 177.7(2) . . . . ?
N4 N3 C7 C6 -0.3(3) . . . . ?
C8 C6 C7 N3 -0.1(3) . . . . ?
C1 C6 C7 N3 173.0(2) . . . . ?
C8 C6 C7 O2 -177.9(3) . . . . ?
C1 C6 C7 O2 -4.8(4) . . . . ?
N3 N4 C8 C6 -0.7(3) . . . . ?
N3 N4 C8 C9 178.2(2) . . . . ?
C7 C6 C8 N4 0.4(2) . . . . ?
C1 C6 C8 N4 -172.9(2) . . . . ?
C7 C6 C8 C9 -178.4(3) . . . . ?
C1 C6 C8 C9 8.3(4) . . . . ?
C2 C1 C10 C15 -156.3(2) . . . . ?
C6 C1 C10 C15 -25.9(3) . . . . ?
C2 C1 C10 C11 26.5(3) . . . . ?
C6 C1 C10 C11 156.9(2) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
C1 C10 C11 C12 178.4(2) . . . . ?
C10 C11 C12 O3 178.0(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C16 O3 C12 C11 -5.3(4) . . . . ?
C16 O3 C12 C13 173.4(3) . . . . ?
C11 C12 C13 O4 178.7(2) . . . . ?
O3 C12 C13 O4 0.0(3) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
O3 C12 C13 C14 -178.7(2) . . . . ?
O4 C13 C14 C15 -178.5(2) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C11 C10 C15 C14 -1.0(3) . . . . ?
C1 C10 C15 C14 -178.2(2) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
C11 C10 C1 C2 26.5(3) . . . . ?
C11 C10 C1 C6 156.9(2) . . . . ?

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
N4 H1N4 O1 0.93(3) 1.93(4) 2.842(3) 168(3) 4_455
O2 H1O2 O1 0.94(5) 1.64(5) 2.579(3) 174(4) .
O4 H1O4 N3 0.82(4) 1.83(4) 2.648(3) 169(4) 2_556
O4 H1O4 N4 0.82(4) 2.70(4) 3.389(3) 142(3) 2_556
C14 H14 O2 0.93 2.60 3.495(3) 160.6 2_556

_refine_diff_density_max         0.110
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027

_shelxl_version_number           2014/6

