# Supplementary Information (SI) for RSC Pharmaceutics.
# 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_CATPH2SO470
_database_code_depnum_ccdc_archive 'CCDC 2444505'
loop_
_audit_author_name
_audit_author_address
'enrico spoletti'
;university of Limerick
Ireland
;
_audit_update_record             
;
2025-09-23 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'0.322(C8 H10 N4 O2), 0.688(C7 H8 N4 O2), H O4 S, 1.688(H2 O)'
_chemical_formula_sum            'C7.31 H14 N4 O7.69 S'
_chemical_formula_weight         313.03

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'
S S 0.1246 0.1234 '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                   10.0724(4)
_cell_length_b                   6.3052(2)
_cell_length_c                   21.2717(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.9730(10)
_cell_angle_gamma                90
_cell_volume                     1343.60(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9307
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             654
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.627
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.129
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0566 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.9282.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20664
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.372
_diffrn_reflns_theta_max         25.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2479
_reflns_number_gt                2145
_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 Aper4'
_computing_cell_refinement       'Bruker Aper4'
_computing_data_reduction        'Bruker Aper4'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    X-seed
_computing_publication_material  X-seed
_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)+(0.0486P)²+0.5816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2479
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_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
N1 N 0.73116(17) 0.7471(3) 0.74576(8) 0.0476(4) Uani 1 1 d . . . . .
C2 C 0.6160(2) 0.8483(3) 0.71865(9) 0.0455(5) Uani 1 1 d . . . . .
N3 N 0.54730(16) 0.7539(2) 0.66629(8) 0.0405(4) Uani 1 1 d . . . . .
C4 C 0.59397(18) 0.5668(3) 0.64599(8) 0.0371(4) Uani 1 1 d . . . . .
C5 C 0.70720(18) 0.4724(3) 0.67194(9) 0.0401(4) Uani 1 1 d . . . . .
C6 C 0.7841(2) 0.5568(3) 0.72621(9) 0.0471(5) Uani 1 1 d . . . . .
N7 N 0.72317(16) 0.2902(3) 0.63710(8) 0.0440(4) Uani 1 1 d . . . . .
H7 H 0.787845 0.201083 0.643299 0.053 Uiso 0.688(5) 1 calc R U P A 1
C8 C 0.6222(2) 0.2775(3) 0.59294(9) 0.0440(5) Uani 1 1 d . . . . .
H8 H 0.609384 0.169836 0.563058 0.053 Uiso 1 1 calc R U . . .
N9 N 0.54025(16) 0.4434(2) 0.59745(7) 0.0410(4) Uani 1 1 d . . . . .
H9 H 0.467090 0.467340 0.573909 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8053(3) 0.8584(5) 0.79950(11) 0.0694(7) Uani 1 1 d . . . . .
H10A H 0.894850 0.804744 0.805827 0.104 Uiso 1 1 calc R U . . .
H10B H 0.761777 0.835196 0.836984 0.104 Uiso 1 1 calc R U . . .
H10C H 0.807324 1.007556 0.790638 0.104 Uiso 1 1 calc R U . . .
O11 O 0.57778(17) 1.0144(3) 0.73972(8) 0.0641(4) Uani 1 1 d . . . . .
C12 C 0.4216(2) 0.8440(3) 0.63844(11) 0.0534(5) Uani 1 1 d . . . . .
H12A H 0.419532 0.843293 0.593217 0.080 Uiso 1 1 calc R U . . .
H12B H 0.413703 0.987120 0.652983 0.080 Uiso 1 1 calc R U . . .
H12C H 0.348743 0.760945 0.650755 0.080 Uiso 1 1 calc R U . . .
O13 O 0.88413(16) 0.4752(3) 0.75354(8) 0.0691(5) Uani 1 1 d . . . . .
C14 C 0.8504(7) 0.1606(12) 0.6393(4) 0.059(2) Uani 0.312(5) 1 d . . P A 2
H14A H 0.914243 0.233758 0.616754 0.089 Uiso 0.312(5) 1 calc R U P A 2
H14B H 0.830983 0.024771 0.620169 0.089 Uiso 0.312(5) 1 calc R U P A 2
H14C H 0.886493 0.141260 0.682534 0.089 Uiso 0.312(5) 1 calc R U P A 2
O20 O 0.1135(4) -0.2069(7) 0.5217(11) 0.092(4) Uani 0.72(3) 1 d G . P B 1
H20A H 0.165389 -0.313543 0.523618 0.137 Uiso 0.72(3) 1 d G U P B 1
H20B H 0.046310 -0.248126 0.539480 0.137 Uiso 0.72(3) 1 d G U P B 1
S15 S 0.25358(5) 0.26957(7) 0.50093(2) 0.04107(17) Uani 1 1 d . . . . .
O16 O 0.29821(14) 0.4726(2) 0.52896(7) 0.0536(4) Uani 1 1 d . . . . .
O17 O 0.1944(2) 0.1563(3) 0.55504(8) 0.0680(5) Uani 1 1 d . . . . .
H17 H 0.167660 0.038596 0.543197 0.102 Uiso 1 1 calc R U . . .
O18 O 0.14876(16) 0.2991(3) 0.45067(7) 0.0622(4) Uani 1 1 d . . . . .
O19 O 0.36307(16) 0.1473(3) 0.48358(10) 0.0730(5) Uani 1 1 d . . . . .
O21 O 0.8983(2) -0.0225(4) 0.65271(11) 0.0651(9) Uani 0.688(5) 1 d G . P A 1
H21A H 0.902160 -0.119312 0.625183 0.098 Uiso 0.688(5) 1 d G U P A 1
H21B H 0.974018 -0.026281 0.674423 0.098 Uiso 0.688(5) 1 d G U P A 1
O22 O 0.1184(12) -0.220(2) 0.5583(12) 0.062(4) Uani 0.28(3) 1 d G . P B 2
H22A H 0.088377 -0.272808 0.590694 0.094 Uiso 0.28(3) 1 d G U P B 2
H22B H 0.171154 -0.313372 0.546513 0.094 Uiso 0.28(3) 1 d G U P B 2


_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
N1 C6 1.394(3) . ?
N1 C2 1.395(3) . ?
N1 C10 1.476(3) . ?
C2 O11 1.217(2) . ?
C2 N3 1.383(3) . ?
N3 C4 1.357(2) . ?
N3 C12 1.456(3) . ?
C4 C5 1.353(3) . ?
C4 N9 1.360(2) . ?
C5 N7 1.385(2) . ?
C5 C6 1.425(3) . ?
C6 O13 1.223(3) . ?
N7 C8 1.313(3) . ?
N7 C14 1.516(7) . ?
N7 H7 0.8600 . ?
C8 N9 1.342(2) . ?
C8 H8 0.9300 . ?
N9 H9 0.8600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O20 H20A 0.8499 . ?
O20 H20B 0.8499 . ?
S15 O19 1.4252(16) . ?
S15 O18 1.4344(16) . ?
S15 O16 1.4628(14) . ?
S15 O17 1.5274(17) . ?
O17 H17 0.8200 . ?
O21 H21A 0.8496 . ?
O21 H21B 0.8502 . ?
O22 H22A 0.8501 . ?
O22 H22B 0.8500 . ?

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 N1 C2 126.72(17) . . ?
C6 N1 C10 117.51(18) . . ?
C2 N1 C10 115.75(18) . . ?
O11 C2 N3 121.1(2) . . ?
O11 C2 N1 121.49(19) . . ?
N3 C2 N1 117.44(17) . . ?
C4 N3 C2 118.00(16) . . ?
C4 N3 C12 121.66(16) . . ?
C2 N3 C12 120.04(17) . . ?
C5 C4 N3 123.95(17) . . ?
C5 C4 N9 108.06(16) . . ?
N3 C4 N9 127.99(17) . . ?
C4 C5 N7 106.67(16) . . ?
C4 C5 C6 122.04(18) . . ?
N7 C5 C6 131.26(18) . . ?
O13 C6 N1 122.83(19) . . ?
O13 C6 C5 125.4(2) . . ?
N1 C6 C5 111.74(17) . . ?
C8 N7 C5 107.98(16) . . ?
C8 N7 C14 125.4(3) . . ?
C5 N7 C14 125.1(3) . . ?
C8 N7 H7 126.0 . . ?
C5 N7 H7 126.0 . . ?
N7 C8 N9 109.75(17) . . ?
N7 C8 H8 125.1 . . ?
N9 C8 H8 125.1 . . ?
C8 N9 C4 107.53(16) . . ?
C8 N9 H9 126.2 . . ?
C4 N9 H9 126.2 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H20A O20 H20B 104.5 . . ?
O19 S15 O18 113.99(11) . . ?
O19 S15 O16 111.44(10) . . ?
O18 S15 O16 111.18(9) . . ?
O19 S15 O17 108.37(12) . . ?
O18 S15 O17 107.92(11) . . ?
O16 S15 O17 103.27(9) . . ?
S15 O17 H17 109.5 . . ?
H21A O21 H21B 104.5 . . ?
H22A O22 H22B 104.5 . . ?

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 N1 C2 O11 179.59(19) . . . . ?
C10 N1 C2 O11 -2.3(3) . . . . ?
C6 N1 C2 N3 -1.2(3) . . . . ?
C10 N1 C2 N3 177.00(18) . . . . ?
O11 C2 N3 C4 -178.80(18) . . . . ?
N1 C2 N3 C4 1.9(3) . . . . ?
O11 C2 N3 C12 -4.9(3) . . . . ?
N1 C2 N3 C12 175.87(18) . . . . ?
C2 N3 C4 C5 -3.4(3) . . . . ?
C12 N3 C4 C5 -177.23(19) . . . . ?
C2 N3 C4 N9 177.43(18) . . . . ?
C12 N3 C4 N9 3.6(3) . . . . ?
N3 C4 C5 N7 -177.96(17) . . . . ?
N9 C4 C5 N7 1.3(2) . . . . ?
N3 C4 C5 C6 3.9(3) . . . . ?
N9 C4 C5 C6 -176.79(17) . . . . ?
C2 N1 C6 O13 -178.1(2) . . . . ?
C10 N1 C6 O13 3.8(3) . . . . ?
C2 N1 C6 C5 1.4(3) . . . . ?
C10 N1 C6 C5 -176.71(19) . . . . ?
C4 C5 C6 O13 176.8(2) . . . . ?
N7 C5 C6 O13 -0.8(4) . . . . ?
C4 C5 C6 N1 -2.6(3) . . . . ?
N7 C5 C6 N1 179.73(19) . . . . ?
C4 C5 N7 C8 -0.7(2) . . . . ?
C6 C5 N7 C8 177.2(2) . . . . ?
C4 C5 N7 C14 165.6(4) . . . . ?
C6 C5 N7 C14 -16.5(5) . . . . ?
C5 N7 C8 N9 -0.2(2) . . . . ?
C14 N7 C8 N9 -166.5(4) . . . . ?
N7 C8 N9 C4 1.0(2) . . . . ?
C5 C4 N9 C8 -1.5(2) . . . . ?
N3 C4 N9 C8 177.79(18) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_CATPH2SO430
_database_code_depnum_ccdc_archive 'CCDC 2444507'
loop_
_audit_author_name
_audit_author_address
'enrico spoletti'
;university of Limerick
Ireland
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-10-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7.673 H10.345 N4 O2, H O4 S, 1.327(H2 O)'
_chemical_formula_sum            'C7.67 H14 N4 O7.33 S'
_chemical_formula_weight         311.60
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.9580(9)
_cell_length_b                   6.2947(6)
_cell_length_c                   21.2757(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.526(3)
_cell_angle_gamma                90
_cell_volume                     1331.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      24.19
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0685 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.9274.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             651
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23060
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        22.498
_diffrn_reflns_theta_max         22.498
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1306
_reflns_number_total             1738
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Apex 4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.081
_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)+(0.0313P)²+1.5482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.1020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Sof(H7)=Sof(O21)=Sof(H21A)=Sof(H21B)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(O22)=Sof(H22A)=Sof(H22B)=1-FVAR(2)
 Sof(O20)=Sof(H20A)=Sof(H20B)=FVAR(2)
3.a Free rotating group:
 O20(H20A,H20B), O21(H21A,H21B,O22,H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C8(H8), N9(H9)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
3.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.2710(3) 0.7570(5) 0.25939(13) 0.0504(8) Uani 1 1 d . . . . .
C2 C 0.3872(4) 0.8543(6) 0.28478(18) 0.0499(10) Uani 1 1 d . . . . .
N3 N 0.4540(3) 0.7563(5) 0.33610(13) 0.0441(7) Uani 1 1 d . . . . .
C4 C 0.4046(4) 0.5683(5) 0.35633(16) 0.0410(9) Uani 1 1 d . . . . .
C5 C 0.2898(4) 0.4796(6) 0.33199(16) 0.0434(9) Uani 1 1 d . . . . .
C6 C 0.2150(4) 0.5657(6) 0.27867(18) 0.0512(10) Uani 1 1 d . . . . .
N7 N 0.2708(3) 0.2964(4) 0.36659(14) 0.0483(8) Uani 1 1 d . . . . .
H7 H 0.204432 0.209431 0.361216 0.058 Uiso 0.327(8) 1 calc R U P A 2
C8 C 0.3719(4) 0.2788(6) 0.40905(17) 0.0482(9) Uani 1 1 d . . . . .
H8 H 0.382894 0.169423 0.438306 0.058 Uiso 1 1 calc R U . . .
N9 N 0.4566(3) 0.4425(5) 0.40376(13) 0.0473(8) Uani 1 1 d . . . . .
H9 H 0.530212 0.463931 0.426185 0.057 Uiso 1 1 calc R U . . .
O10 O 0.1146(3) 0.4888(5) 0.25177(14) 0.0746(9) Uani 1 1 d . . . . .
C11 C 0.2019(4) 0.8664(7) 0.20546(19) 0.0738(13) Uani 1 1 d . . . . .
H11A H 0.115816 0.801344 0.195963 0.111 Uiso 1 1 calc R U . . .
H11B H 0.255235 0.855735 0.169509 0.111 Uiso 1 1 calc R U . . .
H11C H 0.189536 1.013286 0.215726 0.111 Uiso 1 1 calc R U . . .
O12 O 0.4282(3) 1.0216(4) 0.26436(13) 0.0666(8) Uani 1 1 d . . . . .
C13 C 0.5813(4) 0.8438(6) 0.36274(19) 0.0594(11) Uani 1 1 d . . . . .
H13A H 0.581458 0.842844 0.407866 0.089 Uiso 1 1 calc R U . . .
H13B H 0.591217 0.987067 0.348249 0.089 Uiso 1 1 calc R U . . .
H13C H 0.654588 0.759011 0.349581 0.089 Uiso 1 1 calc R U . . .
C14 C 0.1480(6) 0.1620(10) 0.3641(3) 0.062(2) Uani 0.673(8) 1 d . . P A 1
H14A H 0.078620 0.232925 0.385433 0.093 Uiso 0.673(8) 1 calc R U P A 1
H14B H 0.168280 0.028417 0.384290 0.093 Uiso 0.673(8) 1 calc R U P A 1
H14C H 0.117843 0.137795 0.320977 0.093 Uiso 0.673(8) 1 calc R U P A 1
S15 S 0.74691(10) 0.26980(14) 0.49440(4) 0.0470(3) Uani 1 1 d . . . . .
O16 O 0.6346(3) 0.1431(4) 0.51041(14) 0.0722(9) Uani 1 1 d . . . . .
O17 O 0.7023(2) 0.4728(4) 0.46594(12) 0.0586(8) Uani 1 1 d . . . . .
O18 O 0.8177(3) 0.1603(4) 0.44149(12) 0.0695(8) Uani 1 1 d . . . . .
H18 H 0.836976 0.038169 0.451964 0.104 Uiso 1 1 calc R U . . .
O19 O 0.8443(3) 0.3032(4) 0.54647(12) 0.0657(8) Uani 1 1 d . . . . .
O20 O 0.8885(5) -0.2067(10) 0.4696(14) 0.092(6) Uani 0.78(4) 1 d G . P B 1
H20A H 0.839596 -0.316702 0.464175 0.138 Uiso 0.78(4) 1 d G U P B 1
H20B H 0.967436 -0.249043 0.462940 0.138 Uiso 0.78(4) 1 d G U P B 1
O21 O 0.0920(8) -0.0175(14) 0.3495(4) 0.072(4) Uani 0.327(8) 1 d G . P A 2
H21A H 0.028257 -0.048312 0.322700 0.107 Uiso 0.327(8) 1 d G U P A 2
H21B H 0.079478 0.112536 0.358146 0.107 Uiso 0.327(8) 1 d G U P A 2
O22 O 0.8960(10) -0.231(5) 0.433(2) 0.066(7) Uani 0.22(4) 1 d G . P B 2
H22A H 0.978424 -0.263161 0.439877 0.098 Uiso 0.22(4) 1 d G U P B 2
H22B H 0.865442 -0.326271 0.407332 0.098 Uiso 0.22(4) 1 d G U P B 2


_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
N1 C2 1.388(5) . ?
N1 C6 1.399(5) . ?
N1 C11 1.472(5) . ?
C2 N3 1.388(4) . ?
C2 O12 1.219(4) . ?
N3 C4 1.361(4) . ?
N3 C13 1.463(4) . ?
C4 C5 1.348(5) . ?
C4 N9 1.360(4) . ?
C5 C6 1.425(5) . ?
C5 N7 1.387(4) . ?
C6 O10 1.221(4) . ?
N7 H7 0.8600 . ?
N7 C8 1.315(4) . ?
N7 C14 1.485(6) . ?
C8 H8 0.9300 . ?
C8 N9 1.341(4) . ?
N9 H9 0.8600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
S15 O16 1.432(3) . ?
S15 O17 1.471(2) . ?
S15 O18 1.529(3) . ?
S15 O19 1.442(3) . ?
O18 H18 0.8200 . ?
O20 H20A 0.8499 . ?
O20 H20B 0.8501 . ?
O21 H21A 0.8496 . ?
O21 H21B 0.8501 . ?
O22 H22A 0.8501 . ?
O22 H22B 0.8500 . ?

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
C2 N1 C6 127.1(3) . . ?
C2 N1 C11 115.8(3) . . ?
C6 N1 C11 117.1(3) . . ?
N1 C2 N3 117.3(3) . . ?
O12 C2 N1 122.1(4) . . ?
O12 C2 N3 120.6(4) . . ?
C2 N3 C13 120.0(3) . . ?
C4 N3 C2 118.0(3) . . ?
C4 N3 C13 121.7(3) . . ?
C5 C4 N3 123.6(3) . . ?
C5 C4 N9 108.6(3) . . ?
N9 C4 N3 127.7(3) . . ?
C4 C5 C6 122.5(3) . . ?
C4 C5 N7 106.3(3) . . ?
N7 C5 C6 131.1(3) . . ?
N1 C6 C5 111.3(3) . . ?
O10 C6 N1 122.2(4) . . ?
O10 C6 C5 126.5(4) . . ?
C5 N7 H7 125.9 . . ?
C5 N7 C14 126.4(4) . . ?
C8 N7 C5 108.1(3) . . ?
C8 N7 H7 125.9 . . ?
C8 N7 C14 124.8(4) . . ?
N7 C8 H8 125.2 . . ?
N7 C8 N9 109.7(3) . . ?
N9 C8 H8 125.2 . . ?
C4 N9 H9 126.4 . . ?
C8 N9 C4 107.3(3) . . ?
C8 N9 H9 126.4 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 S15 O17 111.17(16) . . ?
O16 S15 O18 109.07(18) . . ?
O16 S15 O19 113.37(18) . . ?
O17 S15 O18 103.29(16) . . ?
O19 S15 O17 111.20(16) . . ?
O19 S15 O18 108.19(17) . . ?
S15 O18 H18 109.5 . . ?
H20A O20 H20B 104.5 . . ?
H21A O21 H21B 104.5 . . ?
H22A O22 H22B 104.5 . . ?

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
_geom_hbond_publ_flag
N9 H9 O17 0.86 1.86 2.715(4) 169.8 . yes
O18 H18 O20 0.82 1.66 2.478(7) 174.8 . yes

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
N1 C2 N3 C4 2.6(5) . . . . ?
N1 C2 N3 C13 176.4(3) . . . . ?
C2 N1 C6 C5 2.8(5) . . . . ?
C2 N1 C6 O10 -177.3(4) . . . . ?
C2 N3 C4 C5 -4.5(5) . . . . ?
C2 N3 C4 N9 177.4(3) . . . . ?
N3 C4 C5 C6 5.7(5) . . . . ?
N3 C4 C5 N7 -177.4(3) . . . . ?
N3 C4 N9 C8 177.2(3) . . . . ?
C4 C5 C6 N1 -4.5(5) . . . . ?
C4 C5 C6 O10 175.7(4) . . . . ?
C4 C5 N7 C8 -0.6(4) . . . . ?
C4 C5 N7 C14 170.0(4) . . . . ?
C5 C4 N9 C8 -1.1(4) . . . . ?
C5 N7 C8 N9 -0.1(4) . . . . ?
C6 N1 C2 N3 -2.1(5) . . . . ?
C6 N1 C2 O12 179.7(4) . . . . ?
C6 C5 N7 C8 175.9(4) . . . . ?
C6 C5 N7 C14 -13.5(6) . . . . ?
N7 C5 C6 N1 179.5(3) . . . . ?
N7 C5 C6 O10 -0.4(7) . . . . ?
N7 C8 N9 C4 0.8(4) . . . . ?
N9 C4 C5 C6 -175.8(3) . . . . ?
N9 C4 C5 N7 1.0(4) . . . . ?
C11 N1 C2 N3 179.4(3) . . . . ?
C11 N1 C2 O12 1.2(5) . . . . ?
C11 N1 C6 C5 -178.6(3) . . . . ?
C11 N1 C6 O10 1.2(5) . . . . ?
O12 C2 N3 C4 -179.2(3) . . . . ?
O12 C2 N3 C13 -5.3(5) . . . . ?
C13 N3 C4 C5 -178.3(3) . . . . ?
C13 N3 C4 N9 3.6(5) . . . . ?
C14 N7 C8 N9 -170.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_THETM01_CATPH2SO430         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: data cut at 2theta=45 due to low resolution at higher
angles, poor crystal quality
;
# end Validation Reply Form
####################################################################### 
# 
# 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_CATPH2SO450
_database_code_depnum_ccdc_archive 'CCDC 2444506'
loop_
_audit_author_name
_audit_author_address
'enrico spoletti'
;university of Limerick
Ireland
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_audit_creation_date             2025-10-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7.541 H10.082 N4 O2, H O4 S, 1.459(H2 O)'
_chemical_formula_sum            'C7.54 H14 N4 O7.46 S'
_chemical_formula_weight         312.14
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.0159(11)
_cell_length_b                   6.2951(7)
_cell_length_c                   21.235(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.423(3)
_cell_angle_gamma                90
_cell_volume                     1334.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3780
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0770 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.8957.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19606
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        20.994
_diffrn_reflns_theta_max         20.994
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1079
_reflns_number_total             1424
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Apex4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1424
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.103
_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)+(0.0461P)²+1.6670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O20) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Others
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-FVAR(1)
 Sof(H7)=Sof(O21)=Sof(H21A)=Sof(H21B)=FVAR(1)
 Sof(O22)=Sof(H22A)=Sof(H22B)=1-FVAR(2)
 Sof(O20)=Sof(H20A)=Sof(H20B)=FVAR(2)
4.a Free rotating group:
 O20(H20A,H20B), O21(H21A,H21B,O22,H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C8(H8), N9(H9)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
4.d Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.7299(4) 0.7546(7) 0.74250(17) 0.0545(11) Uani 1 1 d . . . . .
C2 C 0.6128(5) 0.8534(9) 0.7163(2) 0.0532(13) Uani 1 1 d . . . . .
N3 N 0.5464(4) 0.7557(6) 0.66450(17) 0.0483(10) Uani 1 1 d . . . . .
C4 C 0.5950(5) 0.5689(7) 0.6449(2) 0.0438(12) Uani 1 1 d . . . . .
C5 C 0.7093(5) 0.4764(7) 0.6689(2) 0.0482(12) Uani 1 1 d . . . . .
C6 C 0.7844(5) 0.5643(9) 0.7226(2) 0.0564(14) Uani 1 1 d . . . . .
N7 N 0.7267(4) 0.2951(6) 0.63465(18) 0.0519(11) Uani 1 1 d . . . . .
H7 H 0.792080 0.206943 0.640402 0.062 Uiso 0.459(12) 1 calc R U P A 2
C8 C 0.6261(5) 0.2796(8) 0.5916(2) 0.0507(13) Uani 1 1 d . . . . .
H8 H 0.614748 0.170902 0.562027 0.061 Uiso 1 1 calc R U . . .
N9 N 0.5423(4) 0.4429(6) 0.59649(18) 0.0512(11) Uani 1 1 d . . . . .
H9 H 0.469020 0.464932 0.573564 0.061 Uiso 1 1 calc R U . . .
O10 O 0.8843(4) 0.4857(7) 0.75010(17) 0.0800(12) Uani 1 1 d . . . . .
C11 C 0.8005(6) 0.8648(9) 0.7968(2) 0.0775(17) Uani 1 1 d . . . . .
H11A H 0.808490 1.013085 0.787235 0.116 Uiso 1 1 calc R U . . .
H11B H 0.888075 0.804515 0.805178 0.116 Uiso 1 1 calc R U . . .
H11C H 0.750612 0.848442 0.833371 0.116 Uiso 1 1 calc R U . . .
O12 O 0.5744(4) 1.0195(6) 0.73713(17) 0.0728(11) Uani 1 1 d . . . . .
C13 C 0.4186(5) 0.8449(8) 0.6374(2) 0.0638(15) Uani 1 1 d . . . . .
H13A H 0.411216 0.990138 0.650538 0.096 Uiso 1 1 calc R U . . .
H13B H 0.345583 0.764270 0.651904 0.096 Uiso 1 1 calc R U . . .
H13C H 0.415637 0.838551 0.592162 0.096 Uiso 1 1 calc R U . . .
C14 C 0.8536(10) 0.1665(18) 0.6360(5) 0.070(4) Uani 0.541(12) 1 d . . P A 1
H14A H 0.837149 0.037897 0.612343 0.106 Uiso 0.541(12) 1 calc R U P A 1
H14B H 0.882641 0.132043 0.678911 0.106 Uiso 0.541(12) 1 calc R U P A 1
H14C H 0.921794 0.247502 0.617568 0.106 Uiso 0.541(12) 1 calc R U P A 1
S15 S 0.25297(13) 0.26886(18) 0.50384(6) 0.0517(4) Uani 1 1 d . . . . .
O16 O 0.3645(4) 0.1444(6) 0.48744(19) 0.0787(12) Uani 1 1 d . . . . .
O17 O 0.2977(3) 0.4715(5) 0.53234(16) 0.0639(10) Uani 1 1 d . . . . .
O18 O 0.1861(4) 0.1577(6) 0.55723(16) 0.0753(11) Uani 1 1 d . . . . .
H18 H 0.169937 0.033948 0.547298 0.113 Uiso 1 1 calc R U . . .
O19 O 0.1531(3) 0.3011(6) 0.45228(15) 0.0684(10) Uani 1 1 d . . . . .
O20 O 0.1121(6) -0.2085(13) 0.5280(16) 0.101(7) Uani 0.79(5) 1 d G U P B 1
H20A H 0.162187 -0.313752 0.538472 0.151 Uiso 0.79(5) 1 d G U P B 1
H20B H 0.035343 -0.244273 0.538891 0.151 Uiso 0.79(5) 1 d G U P B 1
O21 O 0.9049(8) -0.0188(15) 0.6502(4) 0.080(4) Uani 0.459(12) 1 d G . P A 2
H21A H 0.967442 -0.038784 0.679000 0.121 Uiso 0.459(12) 1 d G U P A 2
H21B H 0.856146 0.076580 0.665119 0.121 Uiso 0.459(12) 1 d G U P A 2
O22 O 0.1064(11) -0.225(5) 0.566(2) 0.060(9) Uani 0.21(5) 1 d G . P B 2
H22A H 0.023917 -0.258136 0.565346 0.090 Uiso 0.21(5) 1 d G U P B 2
H22B H 0.140474 -0.279305 0.600623 0.090 Uiso 0.21(5) 1 d G U P B 2


_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
N1 C2 1.404(6) . ?
N1 C6 1.395(6) . ?
N1 C11 1.479(6) . ?
C2 N3 1.385(6) . ?
C2 O12 1.209(5) . ?
N3 C4 1.351(6) . ?
N3 C13 1.473(6) . ?
C4 C5 1.349(6) . ?
C4 N9 1.372(5) . ?
C5 C6 1.428(7) . ?
C5 N7 1.372(6) . ?
C6 O10 1.223(6) . ?
N7 H7 0.8600 . ?
N7 C8 1.310(5) . ?
N7 C14 1.505(10) . ?
C8 H8 0.9300 . ?
C8 N9 1.337(6) . ?
N9 H9 0.8600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
S15 O16 1.429(3) . ?
S15 O17 1.467(3) . ?
S15 O18 1.530(3) . ?
S15 O19 1.439(3) . ?
O18 H18 0.8200 . ?
O20 H20A 0.8503 . ?
O20 H20B 0.8501 . ?
O21 H21A 0.8500 . ?
O21 H21B 0.8504 . ?
O22 H22A 0.8500 . ?
O22 H22B 0.8502 . ?

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
C2 N1 C11 115.8(4) . . ?
C6 N1 C2 126.5(4) . . ?
C6 N1 C11 117.7(4) . . ?
N3 C2 N1 117.0(5) . . ?
O12 C2 N1 121.2(5) . . ?
O12 C2 N3 121.8(5) . . ?
C2 N3 C13 119.4(4) . . ?
C4 N3 C2 117.9(4) . . ?
C4 N3 C13 122.3(4) . . ?
N3 C4 N9 127.4(4) . . ?
C5 C4 N3 125.1(4) . . ?
C5 C4 N9 107.5(4) . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 N7 107.3(4) . . ?
N7 C5 C6 131.7(5) . . ?
N1 C6 C5 112.3(5) . . ?
O10 C6 N1 121.9(5) . . ?
O10 C6 C5 125.8(5) . . ?
C5 N7 H7 126.0 . . ?
C5 N7 C14 125.3(5) . . ?
C8 N7 C5 108.1(4) . . ?
C8 N7 H7 126.0 . . ?
C8 N7 C14 125.1(5) . . ?
N7 C8 H8 125.0 . . ?
N7 C8 N9 110.0(4) . . ?
N9 C8 H8 125.0 . . ?
C4 N9 H9 126.4 . . ?
C8 N9 C4 107.2(4) . . ?
C8 N9 H9 126.4 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 S15 O17 111.0(2) . . ?
O16 S15 O18 109.0(2) . . ?
O16 S15 O19 113.7(2) . . ?
O17 S15 O18 103.3(2) . . ?
O19 S15 O17 111.3(2) . . ?
O19 S15 O18 108.1(2) . . ?
S15 O18 H18 109.5 . . ?
H20A O20 H20B 104.5 . . ?
H21A O21 H21B 104.4 . . ?
H22A O22 H22B 104.5 . . ?

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
N1 C2 N3 C4 3.0(6) . . . . ?
N1 C2 N3 C13 176.3(4) . . . . ?
C2 N1 C6 C5 2.0(7) . . . . ?
C2 N1 C6 O10 -176.9(5) . . . . ?
C2 N3 C4 C5 -5.1(7) . . . . ?
C2 N3 C4 N9 177.5(4) . . . . ?
N3 C4 C5 C6 5.5(7) . . . . ?
N3 C4 C5 N7 -177.3(4) . . . . ?
N3 C4 N9 C8 176.9(4) . . . . ?
C4 C5 C6 N1 -3.6(7) . . . . ?
C4 C5 C6 O10 175.3(5) . . . . ?
C4 C5 N7 C8 0.0(5) . . . . ?
C4 C5 N7 C14 166.8(6) . . . . ?
C5 C4 N9 C8 -0.9(5) . . . . ?
C5 N7 C8 N9 -0.5(5) . . . . ?
C6 N1 C2 N3 -1.9(7) . . . . ?
C6 N1 C2 O12 -179.8(5) . . . . ?
C6 C5 N7 C8 176.7(5) . . . . ?
C6 C5 N7 C14 -16.5(9) . . . . ?
N7 C5 C6 N1 180.0(5) . . . . ?
N7 C5 C6 O10 -1.1(9) . . . . ?
N7 C8 N9 C4 0.9(5) . . . . ?
N9 C4 C5 C6 -176.6(4) . . . . ?
N9 C4 C5 N7 0.6(5) . . . . ?
C11 N1 C2 N3 178.7(4) . . . . ?
C11 N1 C2 O12 0.8(7) . . . . ?
C11 N1 C6 C5 -178.5(4) . . . . ?
C11 N1 C6 O10 2.5(7) . . . . ?
O12 C2 N3 C4 -179.1(4) . . . . ?
O12 C2 N3 C13 -5.8(7) . . . . ?
C13 N3 C4 C5 -178.2(4) . . . . ?
C13 N3 C4 N9 4.4(7) . . . . ?
C14 N7 C8 N9 -167.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_THETM01_CATPH2SO450         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: data cut at 2theta=42 due to low resolution at higher
angles, poor crystal quality
;
_vrf_PLAT088_CATPH2SO450         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.85 Note  
RESPONSE: data cut at 2theta=42 due to low resolution at higher
angles, poor crystal quality
;
# end Validation Reply Form
