# 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_CTZ
_database_code_depnum_ccdc_archive 'CCDC 2373514'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi' 'University of Limerick'
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFF003_CTZ                 
;
PROBLEM: _diffrn_measurement_device_type is missing
RESPONSE: Panalytical Empyrean
;
_vrf_PLAT198_CTZ                 
;
PROBLEM: Missing _diffrn_ambient_temperature   Datum ....     Please Add
RESPONSE: 293(2)
;
# Added during the CSD deposition process: Thursday 25 July 2024 03:39 PM
# end Validation Reply Form

#=============================================================================

_audit_creation_method           Expo2014

_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 Cl N3 O4 S2'
_chemical_formula_sum            'C7 H6 Cl N3 O4 S2'
_chemical_formula_weight         295.726

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
H Hydrogen 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C Carbon 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N Nitrogen 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O Oxygen 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S Sulphur 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Chlorine 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_length_a                   7.3334(17)
_cell_length_b                   14.741(3)
_cell_length_c                   10.871(2)
_cell_angle_alpha                90.000
_cell_angle_beta                 114.959(5)
_cell_angle_gamma                90.000
_cell_volume                     1065.4(4)
_cell_formula_units_Z            4
_exptl_crystal_description       powder
_exptl_crystal_colour            colourless
_cell_measurement_temperature    293(2)

_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    6.948
_symmetry_Int_Tables_number      14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y+1/2, z+1/2'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
Cl Cl1 1.2372 0.6891 0.5590 0.02(2) 1.0000 Uiso
S S1 0.3923(3) 0.51014(13) 0.21504(19) 0.003(4) 1.0000 Uiso
S S2 0.8368(3) 0.74837(13) 0.6106(2) 0.033(19) 1.0000 Uiso
O O1 0.316(11) 0.469(5) 0.304(6) 0.05(4) 1.0000 Uiso
O O2 0.300(10) 0.576(3) 0.109(5) 0.004(5) 1.0000 Uiso
O O3 0.980(8) 0.713(5) 0.739(3) 0.004(7) 1.0000 Uiso
O O4 0.634(3) 0.754(4) 0.600(6) 0.003(7) 1.0000 Uiso
N N1 0.4391 0.4257 0.1342 0.01(6) 1.0000 Uiso
N N2 0.7723 0.4630 0.2066 0.01(6) 1.0000 Uiso
N N3 0.9078 0.8373 0.5701 0.04(5) 1.0000 Uiso
C C1 0.6191 0.4124 0.1392 0.02(6) 1.0000 Uiso
C C2 0.7977 0.5303 0.2986 0.01(9) 1.0000 Uiso
C C3 0.6264 0.5572 0.3184 0.02(7) 1.0000 Uiso
C C4 0.6447 0.6208 0.4184 0.01(6) 1.0000 Uiso
C C5 0.8261 0.6649 0.4932 0.01(7) 1.0000 Uiso
C C6 0.9933 0.6398 0.4683 0.01(8) 1.0000 Uiso
C C7 0.9839 0.5757 0.3766 0.01(7) 1.0000 Uiso
H H1 0.6285 0.3591 0.0752 0.0193 1.0000 Uiso
H H2 0.8958 0.4407 0.2003 0.0146 1.0000 Uiso
H H3 0.8480 0.8565 0.4705 0.0439 1.0000 Uiso
H H4 1.0532 0.8477 0.6265 0.0439 1.0000 Uiso
H H5 0.5245 0.6377 0.4446 0.0108 1.0000 Uiso
H H6 1.1129 0.5533 0.3622 0.0105 1.0000 Uiso

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.792731 .
S1 O1 1.44(8) .
S1 O2 1.44(5) .
S1 N1 1.640775 .
S1 C3 1.749703 .
S2 O3 1.44(4) .
S2 O4 1.44(3) .
S2 N3 1.541929 .
S2 C5 1.751267 .
N1 C1 1.312709 .
N2 C1 1.288695 .
N2 C2 1.365438 .
N2 H2 0.992961 .
N3 H3 1.021759 .
N3 H4 0.992069 .
C1 H1 1.070592 .
C2 C3 1.417281 .
C2 C7 1.432941 .
C3 C4 1.398363 .
C4 C5 1.392590 .
C4 H5 1.064535 .
C5 C6 1.411902 .
C6 C7 1.353250 .
C7 H6 1.074768 .

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
Cl1 C6 C5 122.28 . .
Cl1 C6 C7 114.67 . .
O1 S1 O2 130(4) . .
O1 S1 N1 105.46 . .
O1 S1 C3 106.97 . .
O2 S1 N1 102.43 . .
O2 S1 C3 104.52 . .
N1 S1 C3 105.94 . .
S1 N1 C1 121.69 . .
S1 C3 C2 118.94 . .
S1 C3 C4 120.77 . .
O3 S2 O4 114(3) . .
O3 S2 N3 112.61 . .
O3 S2 C5 104.01 . .
O4 S2 N3 112.88 . .
O4 S2 C5 104.57 . .
N3 S2 C5 107.80 . .
S2 N3 H3 119.49 . .
S2 N3 H4 111.05 . .
S2 C5 C4 119.43 . .
S2 C5 C6 123.26 . .
N1 C1 N2 123.83 . .
N1 C1 H1 114.98 . .
C1 N2 C2 130.85 . .
C1 N2 H2 111.79 . .
N2 C1 H1 120.96 . .
C2 N2 H2 116.41 . .
N2 C2 C3 117.30 . .
N2 C2 C7 125.04 . .
H3 N3 H4 118.80 . .
C3 C2 C7 117.65 . .
C2 C3 C4 120.29 . .
C2 C7 C6 120.09 . .
C2 C7 H6 116.62 . .
C3 C4 C5 121.42 . .
C3 C4 H5 123.15 . .
C5 C4 H5 115.42 . .
C4 C5 C6 117.31 . .
C5 C6 C7 123.03 . .
C6 C7 H6 123.20 . .

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
O1 S1 N1 C1 -122.30 . . . .
O2 S1 N1 C1 100.16 . . . .
C3 S1 N1 C1 -9.11 . . . .
O1 S1 C3 C2 123.58 . . . .
O1 S1 C3 C4 -56.78 . . . .
O2 S1 C3 C2 -96.34 . . . .
O2 S1 C3 C4 83.30 . . . .
N1 S1 C3 C2 11.43 . . . .
N1 S1 C3 C4 -168.93 . . . .
O3 S2 N3 H3 158.22 . . . .
O3 S2 N3 H4 14.07 . . . .
O4 S2 N3 H3 -70.91 . . . .
O4 S2 N3 H4 144.95 . . . .
C5 S2 N3 H3 44.06 . . . .
C5 S2 N3 H4 -100.08 . . . .
O3 S2 C5 C4 118.62 . . . .
O3 S2 C5 C6 -62.02 . . . .
O4 S2 C5 C4 -1.28 . . . .
O4 S2 C5 C6 178.08 . . . .
N3 S2 C5 C4 -121.62 . . . .
N3 S2 C5 C6 57.73 . . . .
S1 N1 C1 N2 0.09 . . . .
S1 N1 C1 H1 -174.51 . . . .
C2 N2 C1 N1 9.85 . . . .
C2 N2 C1 H1 -175.85 . . . .
H2 N2 C1 N1 178.09 . . . .
H2 N2 C1 H1 -7.61 . . . .
C1 N2 C2 C3 -6.43 . . . .
C1 N2 C2 C7 173.51 . . . .
H2 N2 C2 C3 -174.24 . . . .
H2 N2 C2 C7 5.71 . . . .
N2 C2 C3 S1 -5.30 . . . .
N2 C2 C3 C4 175.06 . . . .
C7 C2 C3 S1 174.75 . . . .
C7 C2 C3 C4 -4.89 . . . .
N2 C2 C7 C6 -177.97 . . . .
N2 C2 C7 H6 -1.40 . . . .
C3 C2 C7 C6 1.98 . . . .
C3 C2 C7 H6 178.54 . . . .
S1 C3 C4 C5 -174.15 . . . .
S1 C3 C4 H5 7.31 . . . .
C2 C3 C4 C5 5.49 . . . .
C2 C3 C4 H5 -173.05 . . . .
C3 C4 C5 S2 176.48 . . . .
C3 C4 C5 C6 -2.92 . . . .
H5 C4 C5 S2 -4.88 . . . .
H5 C4 C5 C6 175.73 . . . .
S2 C5 C6 Cl1 1.82 . . . .
S2 C5 C6 C7 -179.45 . . . .
C4 C5 C6 Cl1 -178.81 . . . .
C4 C5 C6 C7 -0.08 . . . .
Cl1 C6 C7 C2 179.31 . . . .
Cl1 C6 C7 H6 2.98 . . . .
C5 C6 C7 C2 0.49 . . . .
C5 C6 C7 H6 -175.84 . . . .

_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     1.540598
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_measurement_device_type  ?

# POWDER PROFILE

_pd_meas_2theta_range_min        5.015
_pd_meas_2theta_range_max        39.984
_pd_proc_number_of_points        2058

_pd_proc_ls_prof_R_factor        0.05531
_pd_proc_ls_prof_wR_factor       0.07264
_pd_proc_ls_prof_wR_expected     0.05239

_refine_ls_number_reflns         98
_refine_ls_number_parameters     71
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_R_I_factor            0.03506
_refine_ls_goodness_of_fit_all   1.38648
_refine_ls_restrained_S_all      6.91157

loop_
_pd_meas_2theta_scan
_pd_meas_counts_total
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_bkg_calc

5.015000 731.000000 5.137958 0.000000 795.050903
5.032000 758.000000 5.154958 0.000000 779.999878
5.049000 776.000000 5.171958 0.000000 765.917236
5.066000 705.000000 5.188958 0.000000 752.757324
5.083000 768.000000 5.205957 0.000000 740.473511
5.100000 684.000000 5.222957 0.000000 729.020874
5.117000 715.000000 5.239956 0.000000 718.356567
5.134000 695.000000 5.256956 0.000000 708.440674
5.151000 735.000000 5.273956 0.000000 699.232544
5.168000 727.000000 5.290955 0.000000 690.694702
5.185000 700.000000 5.307955 0.000000 682.790405
5.202000 657.000000 5.324954 0.000000 675.484131
5.219000 687.000000 5.341954 0.000000 668.742065
5.236000 678.000000 5.358954 0.000000 662.532349
5.253000 712.000000 5.375953 0.000000 656.823242
5.270000 677.000000 5.392953 0.000000 651.584961
5.287000 697.000000 5.409952 0.000000 646.788818
5.304000 657.000000 5.426952 0.000000 642.406738
5.321000 672.000000 5.443953 0.000000 638.412598
5.338000 653.000000 5.460952 0.000000 634.781372
5.355000 659.000000 5.477952 0.000000 631.488647
5.372000 654.000000 5.494951 0.000000 628.510864
5.389000 638.000000 5.511950 0.000000 625.826172
5.406000 682.000000 5.528951 0.000000 623.412720
5.423000 652.000000 5.545950 0.000000 621.251099
5.440000 625.000000 5.562950 0.000000 619.321167
5.457000 593.000000 5.579949 0.000000 617.604736
5.474000 602.000000 5.596949 0.000000 616.084351
5.491000 604.000000 5.613948 0.000000 614.742676
5.508000 613.000000 5.630948 0.000000 613.563843
5.525000 615.000000 5.647948 0.000000 612.532715
5.542000 629.000000 5.664947 0.000000 611.634644
5.559000 611.000000 5.681947 0.000000 610.855713
5.576000 597.000000 5.698947 0.000000 610.182861
5.593000 599.000000 5.715947 0.000000 609.603882
5.610000 609.000000 5.732946 0.000000 609.106689
5.627000 621.000000 5.749946 0.000000 608.680054
5.644000 587.000000 5.766945 0.000000 608.313721
5.661000 598.000000 5.783945 0.000000 607.997437
5.678000 627.000000 5.800945 0.000000 607.721802
5.695000 614.000000 5.817944 0.000000 607.478027
5.712000 605.000000 5.834944 0.000000 607.257568
5.729000 564.000000 5.851943 0.000000 607.052612
5.746000 612.000000 5.868943 0.000000 606.855957
5.763000 572.000000 5.885943 0.000000 606.660278
5.780000 620.000000 5.902942 0.000000 606.459351
5.797000 530.000000 5.919942 0.000000 606.247192
5.814000 607.000000 5.936942 0.000000 606.017944
5.831000 526.000000 5.953942 0.000000 605.766479
5.848000 667.000000 5.970942 0.000000 605.488037
5.865000 519.000000 5.987941 0.000000 605.177856
5.882000 594.000000 6.004941 0.000000 604.832031
5.899000 596.000000 6.021940 0.000000 604.446533
5.916000 556.000000 6.038940 0.000000 604.017944
5.933000 539.000000 6.055940 0.000000 603.543213
5.950000 531.000000 6.072939 0.000000 603.019409
5.967000 648.000000 6.089939 0.000000 602.443726
5.984000 559.000000 6.106938 0.000000 601.813965
6.001000 568.000000 6.123938 0.000000 601.128296
6.018000 594.000000 6.140937 0.000000 600.384399
6.035000 564.000000 6.157937 0.000000 599.580933
6.052000 633.000000 6.174937 0.000000 598.716553
6.069000 575.000000 6.191936 0.000000 597.790039
6.086000 607.000000 6.208937 0.000000 596.800415
6.103000 506.000000 6.225936 0.000000 595.747070
6.120000 573.000000 6.242936 0.000000 594.629150
6.137000 529.000000 6.259935 0.000000 593.446533
6.154000 601.000000 6.276935 0.000000 592.198730
6.171000 580.000000 6.293935 0.000000 590.885742
6.188000 564.000000 6.310934 0.000000 589.507935
6.205000 610.000000 6.327934 0.000000 588.064941
6.222000 631.000000 6.344934 0.000000 586.557617
6.239000 613.000000 6.361933 0.000000 584.986206
6.256000 539.000000 6.378932 0.000000 583.351074
6.273000 558.000000 6.395933 0.000000 581.653198
6.290000 557.000000 6.412932 0.000000 579.893311
6.307000 553.000000 6.429932 0.000000 578.072388
6.324000 609.000000 6.446931 0.000000 576.191406
6.341000 586.000000 6.463931 0.000000 574.251221
6.358000 573.000000 6.480931 0.000000 572.252930
6.375000 595.000000 6.497931 0.000000 570.197998
6.392000 626.000000 6.514930 0.000000 568.087769
6.409000 620.000000 6.531929 0.000000 565.923340
6.426000 594.000000 6.548929 0.000000 563.706177
6.443000 571.000000 6.565929 0.000000 561.437866
6.460000 550.000000 6.582929 0.000000 559.119751
6.477000 590.000000 6.599928 0.000000 556.753418
6.494000 564.000000 6.616928 0.000000 554.340454
6.511000 560.000000 6.633927 0.000000 551.882568
6.528000 555.000000 6.650928 0.000000 549.381104
6.545000 588.000000 6.667927 0.000000 546.838135
6.562000 625.000000 6.684927 0.000000 544.255249
6.579000 587.000000 6.701926 0.000000 541.633911
6.596000 582.000000 6.718925 0.000000 538.976196
6.613000 578.000000 6.735926 0.000000 536.283569
6.630000 570.000000 6.752925 0.000000 533.557983
6.647000 562.000000 6.769925 0.000000 530.801270
6.664000 550.000000 6.786924 0.000000 528.014771
6.681000 601.000000 6.803924 0.000000 525.200806
6.698000 586.000000 6.820924 0.000000 522.360474
6.715000 567.000000 6.837924 0.000000 519.496216
6.732000 561.000000 6.854923 0.000000 516.609497
6.749000 587.000000 6.871923 0.000000 513.702026
6.766000 527.000000 6.888922 0.000000 510.775604
6.783000 563.000000 6.905922 0.000000 507.832001
6.800000 508.000000 6.922922 0.000000 504.872650
6.817000 553.000000 6.939921 0.000000 501.899506
6.834000 553.000000 6.956921 0.000000 498.914459
6.851000 580.000000 6.973920 0.000000 495.918854
6.868000 527.000000 6.990921 0.000000 492.914215
6.885000 550.000000 7.007920 0.000000 489.902374
6.902000 495.000000 7.024920 0.000000 486.885040
6.919000 555.000000 7.041919 0.000000 483.863800
6.936000 522.000000 7.058919 0.000000 480.839813
6.953000 460.000000 7.075919 0.000000 477.814728
6.970000 537.000000 7.092919 0.000000 474.790436
6.987000 491.000000 7.109918 0.000000 471.768036
7.004000 492.000000 7.126917 0.000000 468.749298
7.021000 456.000000 7.143917 0.000000 465.734955
7.038000 500.000000 7.160917 0.000000 462.726837
7.055000 462.000000 7.177917 0.000000 459.726410
7.072000 464.000000 7.194916 0.000000 456.735016
7.089000 450.000000 7.211915 0.000000 453.753693
7.106000 473.000000 7.228916 0.000000 450.783600
7.123000 466.000000 7.245916 0.000000 447.826202
7.140000 448.000000 7.262915 0.000000 444.882660
7.157000 457.000000 7.279915 0.000000 441.954132
7.174000 415.000000 7.296914 0.000000 439.041656
7.191000 438.000000 7.313914 0.000000 436.146332
7.208000 403.000000 7.330914 0.000000 433.269196
7.225000 407.000000 7.347913 0.000000 430.411285
7.242000 413.000000 7.364913 0.000000 427.573639
7.259000 368.000000 7.381912 0.045840 424.757172
7.276000 382.000000 7.398912 0.046340 421.962921
7.293000 390.000000 7.415913 0.046848 419.191254
7.310000 421.000000 7.432912 0.047365 416.443756
7.327000 373.000000 7.449911 0.047890 413.720978
7.344000 356.000000 7.466911 0.048423 411.023285
7.361000 341.000000 7.483911 0.048965 408.351776
7.378000 400.000000 7.500911 0.049516 405.707184
7.395000 409.000000 7.517910 0.050076 403.090057
7.412000 408.000000 7.534909 0.050646 400.501495
7.429000 369.000000 7.551909 0.051224 397.941254
7.446000 370.000000 7.568909 0.051813 395.410614
7.463000 377.000000 7.585909 0.052412 392.909943
7.480000 377.000000 7.602909 0.053020 390.439484
7.497000 354.000000 7.619908 0.053639 388.000275
7.514000 350.000000 7.636908 0.054269 385.592316
7.531000 386.000000 7.653907 0.054909 383.216217
7.548000 351.000000 7.670907 0.055561 380.872101
7.565000 334.000000 7.687907 0.056224 378.560760
7.582000 333.000000 7.704906 0.056899 376.282379
7.599000 350.000000 7.721906 0.057585 374.037140
7.616000 364.000000 7.738905 0.058284 371.825470
7.633000 344.000000 7.755905 0.058995 369.647430
7.650000 345.000000 7.772905 0.059719 367.503448
7.667000 334.000000 7.789905 0.060455 365.393402
7.684000 336.000000 7.806904 0.061206 363.317902
7.701000 333.000000 7.823904 0.061969 361.276947
7.718000 346.000000 7.840904 0.062747 359.270355
7.735000 343.000000 7.857903 0.063539 357.298615
7.752000 344.000000 7.874903 0.064346 355.361603
7.769000 313.000000 7.891902 0.065168 353.459503
7.786000 346.000000 7.908902 0.066006 351.592072
7.803000 289.000000 7.925902 0.066859 349.759674
7.820000 400.000000 7.942901 0.067728 347.961945
7.837000 317.000000 7.959901 0.068614 346.198944
7.854000 363.000000 7.976901 0.069517 344.470734
7.871000 350.000000 7.993901 0.070438 342.777069
7.888000 334.000000 8.010900 0.071376 341.118073
7.905000 316.000000 8.027900 0.072333 339.493256
7.922000 337.000000 8.044899 0.073308 337.902924
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39.831001 217.000000 39.953503 16.222267 171.604980
39.848000 209.000000 39.970501 14.834017 173.877945
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39.882000 210.000000 40.004505 12.841447 179.022507
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39.916000 179.000000 40.038506 11.458989 185.040039
39.933002 168.000000 40.055508 10.891326 188.407440
39.950001 179.000000 40.072506 10.373436 192.030304
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_reflns_number_total             98
_reflns_limit_h_min              0
_reflns_limit_h_max              3
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              -4
_reflns_limit_l_max              4
_reflns_d_resolution_high        8.193
_reflns_d_resolution_low         2.263
_chemical_name_common            Chlorothiazide
_exptl_crystal_recrystallization_method 'Spray Drying'
