# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ortho1_a
_audit_block_doi                 10.5517/ccdc.csd.cc2kbk9s
_database_code_depnum_ccdc_archive 'CCDC 2363635'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2024-06-18 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        N-(3-Hydroxyphenyl)acetamide
_chemical_name_common            Metacetamol
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16

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 a 21'
_space_group_name_Hall           'P 2c -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, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.505(3)
_cell_length_b                   16.986(4)
_cell_length_c                   4.2444(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     757.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.11

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.173
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   'R.H.Blessing Acta Crystallogr.A 1995,51,33'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Micro Focustube'
_diffrn_measurement_device_type  'Bruker APEX-III CMOS Photon Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41063
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         27.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1682
_reflns_number_gt                1513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and Encifer'
_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)+(0.0432P)²+0.0908P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1682
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
O2 O 0.75098(14) 0.75962(8) 0.5782(6) 0.0587(5) Uani 1 1 d . . . . .
O1 O 0.64043(13) 0.38819(7) 0.2974(5) 0.0583(5) Uani 1 1 d . . . . .
H1 H 0.686522 0.354925 0.216258 0.087 Uiso 1 1 calc R U . . .
N1 N 0.62331(14) 0.65316(8) 0.6135(5) 0.0383(4) Uani 1 1 d . . . . .
H1A H 0.550812 0.637921 0.685154 0.046 Uiso 1 1 calc R U . . .
C1 C 0.69251(17) 0.59554(10) 0.4443(5) 0.0334(4) Uani 1 1 d . . . . .
C7 C 0.65403(19) 0.72786(10) 0.6784(5) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.64002(16) 0.52054(10) 0.4438(5) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.563824 0.511360 0.549144 0.044 Uiso 1 1 calc R U . . .
C3 C 0.69958(18) 0.45967(11) 0.2891(6) 0.0388(5) Uani 1 1 d . . . . .
C6 C 0.8058(2) 0.60939(11) 0.2876(6) 0.0422(5) Uani 1 1 d . . . . .
H6 H 0.841880 0.659375 0.285629 0.051 Uiso 1 1 calc R U . . .
C4 C 0.81291(19) 0.47295(11) 0.1300(6) 0.0432(5) Uani 1 1 d . . . . .
H4 H 0.853396 0.432267 0.022950 0.052 Uiso 1 1 calc R U . . .
C5 C 0.86424(19) 0.54734(12) 0.1337(6) 0.0461(5) Uani 1 1 d . . . . .
H5 H 0.940742 0.556279 0.029429 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5605(2) 0.77120(12) 0.8798(6) 0.0509(6) Uani 1 1 d . . . . .
H8A H 0.605367 0.804846 1.023581 0.076 Uiso 1 1 calc R U . . .
H8B H 0.510160 0.734101 0.996470 0.076 Uiso 1 1 calc R U . . .
H8C H 0.505833 0.802458 0.748548 0.076 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
O2 C7 1.228(2) . ?
O1 C3 1.364(2) . ?
O1 H1 0.8200 . ?
N1 C7 1.338(2) . ?
N1 C1 1.415(2) . ?
N1 H1A 0.8600 . ?
C1 C6 1.383(3) . ?
C1 C2 1.388(2) . ?
C7 C8 1.496(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C6 C5 1.384(3) . ?
C6 H6 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C3 O1 H1 109.5 . . ?
C7 N1 C1 129.55(17) . . ?
C7 N1 H1A 115.2 . . ?
C1 N1 H1A 115.2 . . ?
C6 C1 C2 119.80(17) . . ?
C6 C1 N1 124.63(16) . . ?
C2 C1 N1 115.57(17) . . ?
O2 C7 N1 123.03(19) . . ?
O2 C7 C8 121.75(18) . . ?
N1 C7 C8 115.21(18) . . ?
C3 C2 C1 120.66(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O1 C3 C2 116.70(18) . . ?
O1 C3 C4 123.25(17) . . ?
C2 C3 C4 120.04(17) . . ?
C1 C6 C5 118.63(17) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C5 C4 C3 118.74(18) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C7 N1 C1 C6 -5.6(4) . . . . ?
C7 N1 C1 C2 173.9(2) . . . . ?
C1 N1 C7 O2 4.1(4) . . . . ?
C1 N1 C7 C8 -176.8(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
N1 C1 C2 C3 -179.47(19) . . . . ?
C1 C2 C3 O1 -179.2(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C5 179.4(2) . . . . ?
O1 C3 C4 C5 179.4(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C1 C6 C5 C4 0.5(4) . . . . ?

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 O2 0.93 2.31 2.892(2) 119.9 .
N1 H1A O1 0.86 2.11 2.963(2) 170.2 2_665
O1 H1 O2 0.82 1.84 2.634(2) 161.7 4_644
O1 H1 O2 0.82 1.84 2.634(2) 161.7 4_644
N1 H1A O1 0.86 2.11 2.963(2) 170.2 2_665
C6 H6 O2 0.93 2.31 2.892(2) 119.9 .

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 'Solution Crystallization'
####################################################################### 
# 
# 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_M08_a_a_a_a_a_a
_audit_block_doi                 10.5517/ccdc.csd.cc2ph4bp
_database_code_depnum_ccdc_archive 'CCDC 2487202'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2025-09-11 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        N(3hydroxyphenylacetamide)acetonehemisolvate
_chemical_name_common            'Metacetamol acetone hemisolvate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C3 H6 O'
_chemical_formula_sum            'C19 H24 N2 O5'
_chemical_formula_weight         360.40

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.136(3)
_cell_length_b                   9.124(2)
_cell_length_c                   17.679(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.308(8)
_cell_angle_gamma                90
_cell_volume                     1931.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4558
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.42

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.6208
_shelx_estimated_absorpt_T_max   0.7440
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6208
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_process_details   'R.H.Blessing Acta Crystallogr.A 1995,51,33'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Micro Focustube'
_diffrn_measurement_device_type  'Sealed Micro Focustube'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13390
_diffrn_reflns_av_unetI/netI     0.3965
_diffrn_reflns_av_R_equivalents  0.2850
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4558
_reflns_number_gt                1203
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4558
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3591
_refine_ls_R_factor_gt           0.1004
_refine_ls_wR_factor_ref         0.2678
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_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
O2 O 0.6565(3) 0.9863(4) 0.6760(2) 0.0595(11) Uani 1 1 d . . . . .
H10 H 0.635330 1.041996 0.640198 0.089 Uiso 1 1 calc R U . . .
O1 O 0.4020(3) 0.8481(4) 0.4467(2) 0.0702(13) Uani 1 1 d . . . . .
N2 N 0.8438(3) 1.0007(4) 0.8157(2) 0.0467(12) Uani 1 1 d . . . . .
H4 H 0.796664 1.004823 0.773860 0.056 Uiso 1 1 calc R U . . .
O4 O 1.0930(4) 0.6609(4) 0.9696(2) 0.0809(14) Uani 1 1 d . . . . .
H8 H 1.102088 0.731419 0.998726 0.121 Uiso 1 1 calc R U . . .
N1 N 0.4036(4) 0.6478(4) 0.5220(2) 0.0583(13) Uani 1 1 d . . . . .
H15 H 0.377967 0.560010 0.522537 0.070 Uiso 1 1 calc R U . . .
O3 O 0.9074(4) 1.1272(4) 0.9227(2) 0.0825(14) Uani 1 1 d . . . . .
O5 O 0.3194(4) 0.3535(4) 0.5473(2) 0.0879(15) Uani 1 1 d . . . . .
C8 C 0.5947(4) 0.8604(5) 0.6670(3) 0.0448(14) Uani 1 1 d . . . . .
C7 C 0.5306(4) 0.8235(5) 0.5978(3) 0.0427(14) Uani 1 1 d . . . . .
H14 H 0.527155 0.886092 0.555987 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4718(4) 0.6937(5) 0.5910(3) 0.0463(14) Uani 1 1 d . . . . .
C13 C 0.9026(4) 0.8664(6) 0.8284(3) 0.0422(13) Uani 1 1 d . . . . .
C18 C 0.8501(5) 1.1234(6) 0.8592(3) 0.0526(15) Uani 1 1 d . . . . .
C12 C 0.8887(4) 0.7683(6) 0.7677(3) 0.0536(15) Uani 1 1 d . . . . .
H5 H 0.843585 0.791395 0.721572 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5983(4) 0.7688(6) 0.7295(3) 0.0528(15) Uani 1 1 d . . . . .
H11 H 0.639803 0.794376 0.776528 0.063 Uiso 1 1 calc R U . . .
C15 C 1.0247(5) 0.6997(6) 0.9040(3) 0.0540(15) Uani 1 1 d . . . . .
C14 C 0.9713(4) 0.8344(6) 0.8964(3) 0.0515(15) Uani 1 1 d . . . . .
H9 H 0.981619 0.901758 0.936429 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3731(5) 0.7221(6) 0.4558(3) 0.0563(16) Uani 1 1 d . . . . .
C2 C 0.2670(5) 0.2440(6) 0.5263(3) 0.0587(17) Uani 1 1 d . . . . .
C16 C 0.9438(5) 0.6350(6) 0.7774(3) 0.0593(17) Uani 1 1 d . . . . .
H6 H 0.934077 0.567873 0.737326 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4772(5) 0.5996(6) 0.6525(3) 0.0665(18) Uani 1 1 d . . . . .
H13 H 0.438935 0.510848 0.647406 0.080 Uiso 1 1 calc R U . . .
C17 C 1.0116(5) 0.5992(6) 0.8437(4) 0.0679(18) Uani 1 1 d . . . . .
H7 H 1.048444 0.509515 0.848879 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5397(5) 0.6387(6) 0.7212(3) 0.0664(18) Uani 1 1 d . . . . .
H12 H 0.542577 0.576261 0.763034 0.080 Uiso 1 1 calc R U . . .
C19 C 0.7849(5) 1.2534(5) 0.8253(3) 0.0727(19) Uani 1 1 d . . . . .
H1 H 0.756960 1.306514 0.865072 0.109 Uiso 1 1 calc R U . . .
H3 H 0.723397 1.221007 0.787869 0.109 Uiso 1 1 calc R U . . .
H2 H 0.832408 1.316097 0.801155 0.109 Uiso 1 1 calc R U . . .
C4 C 0.2997(5) 0.6401(6) 0.3942(3) 0.081(2) Uani 1 1 d . . . . .
H16 H 0.236794 0.700018 0.373775 0.122 Uiso 1 1 calc R U . . .
H17 H 0.273877 0.551794 0.415044 0.122 Uiso 1 1 calc R U . . .
H18 H 0.341105 0.615875 0.353985 0.122 Uiso 1 1 calc R U . . .
C3 C 0.2826(6) 0.1061(6) 0.5700(3) 0.078(2) Uani 1 1 d . . . . .
H24 H 0.354297 0.106722 0.602174 0.117 Uiso 1 1 calc R U . . .
H22 H 0.278444 0.024914 0.535099 0.117 Uiso 1 1 calc R U . . .
H23 H 0.225108 0.096779 0.601164 0.117 Uiso 1 1 calc R U . . .
C1 C 0.1852(5) 0.2411(7) 0.4525(3) 0.091(2) Uani 1 1 d . . . . .
H19 H 0.168523 0.339662 0.435368 0.137 Uiso 1 1 calc R U . . .
H20 H 0.117805 0.193227 0.460901 0.137 Uiso 1 1 calc R U . . .
H21 H 0.217241 0.188651 0.414320 0.137 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
O2 C8 1.368(5) . ?
O2 H10 0.8200 . ?
O1 C5 1.220(6) . ?
N2 C18 1.352(6) . ?
N2 C13 1.417(6) . ?
N2 H4 0.8600 . ?
O4 C15 1.359(6) . ?
O4 H8 0.8200 . ?
N1 C5 1.352(6) . ?
N1 C6 1.421(6) . ?
N1 H15 0.8600 . ?
O3 C18 1.223(6) . ?
O5 C2 1.210(5) . ?
C8 C9 1.379(6) . ?
C8 C7 1.381(6) . ?
C7 C6 1.378(6) . ?
C7 H14 0.9300 . ?
C6 C11 1.378(7) . ?
C13 C14 1.380(7) . ?
C13 C12 1.387(7) . ?
C18 C19 1.497(6) . ?
C12 C16 1.385(6) . ?
C12 H5 0.9300 . ?
C9 C10 1.380(6) . ?
C9 H11 0.9300 . ?
C15 C14 1.385(7) . ?
C15 C17 1.394(7) . ?
C14 H9 0.9300 . ?
C5 C4 1.493(7) . ?
C2 C3 1.473(7) . ?
C2 C1 1.505(8) . ?
C16 C17 1.358(7) . ?
C16 H6 0.9300 . ?
C11 C10 1.371(7) . ?
C11 H13 0.9300 . ?
C17 H7 0.9300 . ?
C10 H12 0.9300 . ?
C19 H1 0.9600 . ?
C19 H3 0.9600 . ?
C19 H2 0.9600 . ?
C4 H16 0.9600 . ?
C4 H17 0.9600 . ?
C4 H18 0.9600 . ?
C3 H24 0.9600 . ?
C3 H22 0.9600 . ?
C3 H23 0.9600 . ?
C1 H19 0.9600 . ?
C1 H20 0.9600 . ?
C1 H21 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
C8 O2 H10 109.5 . . ?
C18 N2 C13 130.2(5) . . ?
C18 N2 H4 114.9 . . ?
C13 N2 H4 114.9 . . ?
C15 O4 H8 109.5 . . ?
C5 N1 C6 129.4(4) . . ?
C5 N1 H15 115.3 . . ?
C6 N1 H15 115.3 . . ?
O2 C8 C9 118.1(5) . . ?
O2 C8 C7 121.8(5) . . ?
C9 C8 C7 120.1(5) . . ?
C6 C7 C8 119.8(5) . . ?
C6 C7 H14 120.1 . . ?
C8 C7 H14 120.1 . . ?
C7 C6 C11 120.6(5) . . ?
C7 C6 N1 123.4(5) . . ?
C11 C6 N1 116.1(5) . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 N2 122.6(5) . . ?
C12 C13 N2 116.2(5) . . ?
O3 C18 N2 121.1(5) . . ?
O3 C18 C19 122.1(5) . . ?
N2 C18 C19 116.8(5) . . ?
C16 C12 C13 118.4(5) . . ?
C16 C12 H5 120.8 . . ?
C13 C12 H5 120.8 . . ?
C8 C9 C10 119.2(5) . . ?
C8 C9 H11 120.4 . . ?
C10 C9 H11 120.4 . . ?
O4 C15 C14 121.6(5) . . ?
O4 C15 C17 117.4(5) . . ?
C14 C15 C17 121.1(5) . . ?
C13 C14 C15 118.6(5) . . ?
C13 C14 H9 120.7 . . ?
C15 C14 H9 120.7 . . ?
O1 C5 N1 122.9(5) . . ?
O1 C5 C4 121.8(5) . . ?
N1 C5 C4 115.4(5) . . ?
O5 C2 C3 121.9(5) . . ?
O5 C2 C1 121.3(6) . . ?
C3 C2 C1 116.8(5) . . ?
C17 C16 C12 122.1(5) . . ?
C17 C16 H6 119.0 . . ?
C12 C16 H6 119.0 . . ?
C10 C11 C6 119.0(5) . . ?
C10 C11 H13 120.5 . . ?
C6 C11 H13 120.5 . . ?
C16 C17 C15 118.6(6) . . ?
C16 C17 H7 120.7 . . ?
C15 C17 H7 120.7 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H12 119.3 . . ?
C9 C10 H12 119.3 . . ?
C18 C19 H1 109.5 . . ?
C18 C19 H3 109.5 . . ?
H1 C19 H3 109.5 . . ?
C18 C19 H2 109.5 . . ?
H1 C19 H2 109.5 . . ?
H3 C19 H2 109.5 . . ?
C5 C4 H16 109.5 . . ?
C5 C4 H17 109.5 . . ?
H16 C4 H17 109.5 . . ?
C5 C4 H18 109.5 . . ?
H16 C4 H18 109.5 . . ?
H17 C4 H18 109.5 . . ?
C2 C3 H24 109.5 . . ?
C2 C3 H22 109.5 . . ?
H24 C3 H22 109.5 . . ?
C2 C3 H23 109.5 . . ?
H24 C3 H23 109.5 . . ?
H22 C3 H23 109.5 . . ?
C2 C1 H19 109.5 . . ?
C2 C1 H20 109.5 . . ?
H19 C1 H20 109.5 . . ?
C2 C1 H21 109.5 . . ?
H19 C1 H21 109.5 . . ?
H20 C1 H21 109.5 . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050


# start Validation Reply Form
_vrf_RINTA01_M08_a_a_a_a_a_a     
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The elevated Rint reflects the instability of the acetone hemisolvate crystal, which began to lose solvent and convert to another form when exposed to the atmosphere. 
To minimise deterioration, the crystal was coated with liquid paraffin and a fast scan measurement was performed. 
This strategy preserved a usable crystal, but symmetry-equivalent reflections, especially at high angles, show reduced agreement. 
All reflections were retained, refinement was against F^2, and the resulting structure is chemically reasonable.
;
_vrf_PLAT020_M08_a_a_a_a_a_a     
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.285 Report
RESPONSE: As explained for RINTA01_M08_a_a_a_a_a_a, the high merging R value is due to weak diffraction and some solvent loss during data collection. 
Although paraffin coating and fast scanning helped slow down the damage, there was still some variation between equivalent reflections. 
Still, the refinement worked well, and the final model makes chemical sense.
;
_vrf_PLAT026_M08_a_a_a_a_a_a     
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 26% Check
RESPONSE: Only about 26% of the unique reflections were above I > 2\s(I) because the solvate crystal was weak and unstable, and we had to use a short data collection to reduce solvent loss. 
Even so, we used all the measured data in the F^2^ refinement, and the final structure is complete, chemically sensible, and reliable.
;
# end Validation Reply Form

