# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_24016b_a
_database_code_depnum_ccdc_archive 'CCDC 2495772'
loop_
_audit_author_name
_audit_author_address
'Alex Lovstedt'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2026-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
; 
'3-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)-1-methylpyridin-1-ium iodide' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H25 N4 S, I'
_chemical_formula_sum            'C15 H25 I N4 S'
_chemical_formula_weight         420.35

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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.3559(3)
_cell_length_b                   9.8324(4)
_cell_length_c                   24.4571(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1768.89(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   0.6503
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.929
_shelx_estimated_absorpt_T_min   0.723
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS, Krause, L. et al. J. Appl. Cryst. (2015), 48, 3-10.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   micro-focus
_diffrn_measurement_device_type  'Bruker Photon-III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32843
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         30.618
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5450
_reflns_number_gt                5356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.996

_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXT, Sheldrick, G. M. Acta Cryst. (2015) A71, 3-8.'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0125P)²+0.4990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 
; 
 Flack x determined using 2267 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.024(6)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5450
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0151
_refine_ls_wR_factor_ref         0.0344
_refine_ls_wR_factor_gt          0.0342
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_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
I1 I 0.47009(2) 1.04579(2) 0.57793(2) 0.01390(3) Uani 1 1 d . . . . .
S1 S 0.38822(8) 0.99900(5) 0.38623(2) 0.01918(11) Uani 1 1 d . . . . .
N1 N 0.3617(3) 0.81461(18) 0.46484(7) 0.0159(3) Uani 1 1 d . . . . .
H1N H 0.392(4) 0.877(3) 0.4848(11) 0.024 Uiso 1 1 d . U . . .
N2 N 0.2554(2) 0.74698(17) 0.38054(7) 0.0124(3) Uani 1 1 d . . . . .
H2N H 0.210(4) 0.675(3) 0.3976(11) 0.019 Uiso 1 1 d . U . . .
N3 N 0.4352(2) 0.45006(18) 0.48878(6) 0.0140(3) Uani 1 1 d . . . . .
N4 N 0.4438(2) 0.54853(18) 0.32288(6) 0.0132(3) Uani 1 1 d . . . . .
C1 C 0.3320(3) 0.84428(19) 0.41031(7) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.3733(3) 0.6867(2) 0.48987(8) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.4263(3) 0.56999(19) 0.46201(8) 0.0143(4) Uani 1 1 d . . . . .
H3 H 0.456084 0.574594 0.424261 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3992(3) 0.4388(2) 0.54257(8) 0.0178(4) Uani 1 1 d . . . . .
H4 H 0.407458 0.352858 0.560143 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3503(3) 0.5524(2) 0.57193(8) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.326791 0.545389 0.610023 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3355(3) 0.6768(2) 0.54588(8) 0.0167(4) Uani 1 1 d . . . . .
H6 H 0.299809 0.755254 0.565885 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4751(4) 0.32564(19) 0.45672(8) 0.0175(4) Uani 1 1 d . . . . .
H7A H 0.492585 0.248733 0.481663 0.026 Uiso 1 1 calc R U . . .
H7B H 0.585967 0.339597 0.435204 0.026 Uiso 1 1 calc R U . . .
H7C H 0.373253 0.306331 0.432091 0.026 Uiso 1 1 calc R U . . .
C8 C 0.2399(3) 0.74873(19) 0.32110(7) 0.0111(3) Uani 1 1 d . . . . .
H8 H 0.335439 0.810639 0.306032 0.013 Uiso 1 1 calc R U . . .
C9 C 0.2746(3) 0.60414(19) 0.29948(8) 0.0110(3) Uani 1 1 d . . . . .
H9 H 0.172926 0.546025 0.313301 0.013 Uiso 1 1 calc R U . . .
C10 C 0.2608(3) 0.6041(2) 0.23664(8) 0.0139(4) Uani 1 1 d . . . . .
H10A H 0.358948 0.661301 0.221210 0.017 Uiso 1 1 calc R U . . .
H10B H 0.277455 0.510257 0.222845 0.017 Uiso 1 1 calc R U . . .
C11 C 0.0756(3) 0.6587(2) 0.21762(8) 0.0162(4) Uani 1 1 d . . . . .
H11A H 0.073260 0.662448 0.177173 0.019 Uiso 1 1 calc R U . . .
H11B H -0.021513 0.595875 0.229708 0.019 Uiso 1 1 calc R U . . .
C12 C 0.0387(3) 0.80031(19) 0.24060(7) 0.0161(4) Uani 1 1 d . . . . .
H12A H -0.084752 0.829959 0.229786 0.019 Uiso 1 1 calc R U . . .
H12B H 0.127243 0.865611 0.225074 0.019 Uiso 1 1 calc R U . . .
C13 C 0.0540(3) 0.8004(2) 0.30288(7) 0.0133(4) Uani 1 1 d . . . . .
H13A H 0.035419 0.893977 0.316777 0.016 Uiso 1 1 calc R U . . .
H13B H -0.042144 0.741758 0.318547 0.016 Uiso 1 1 calc R U . . .
C14 C 0.6089(3) 0.6179(2) 0.30542(10) 0.0235(5) Uani 1 1 d . . . . .
H14A H 0.714096 0.577434 0.323895 0.035 Uiso 1 1 calc R U . . .
H14B H 0.600737 0.714526 0.314863 0.035 Uiso 1 1 calc R U . . .
H14C H 0.623083 0.608236 0.265766 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4599(4) 0.4023(2) 0.31340(8) 0.0184(4) Uani 1 1 d . . . . .
H15A H 0.566968 0.367438 0.332668 0.028 Uiso 1 1 calc R U . . .
H15B H 0.472744 0.385121 0.274119 0.028 Uiso 1 1 calc R U . . .
H15C H 0.350723 0.356354 0.327044 0.028 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
S1 C1 1.683(2) . ?
N1 C1 1.383(2) . ?
N1 C2 1.401(3) . ?
N1 H1N 0.82(3) . ?
N2 C1 1.328(2) . ?
N2 C8 1.458(2) . ?
N2 H2N 0.89(3) . ?
N3 C4 1.346(2) . ?
N3 C3 1.350(2) . ?
N3 C7 1.483(3) . ?
N4 C14 1.457(3) . ?
N4 C15 1.461(3) . ?
N4 C9 1.475(2) . ?
C2 C3 1.390(3) . ?
C2 C6 1.401(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.525(3) . ?
C8 C9 1.538(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.540(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.536(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.527(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1 N1 C2 128.33(17) . . ?
C1 N1 H1N 117.3(19) . . ?
C2 N1 H1N 113.7(19) . . ?
C1 N2 C8 124.84(16) . . ?
C1 N2 H2N 118.5(17) . . ?
C8 N2 H2N 116.6(17) . . ?
C4 N3 C3 122.41(18) . . ?
C4 N3 C7 119.21(17) . . ?
C3 N3 C7 118.27(15) . . ?
C14 N4 C15 110.25(17) . . ?
C14 N4 C9 114.61(16) . . ?
C15 N4 C9 111.82(17) . . ?
N2 C1 N1 116.36(17) . . ?
N2 C1 S1 124.32(15) . . ?
N1 C1 S1 119.30(14) . . ?
C3 C2 C6 118.53(18) . . ?
C3 C2 N1 122.94(18) . . ?
C6 C2 N1 118.49(18) . . ?
N3 C3 C2 119.79(18) . . ?
N3 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
N3 C4 C5 119.66(19) . . ?
N3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.88(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C2 119.71(19) . . ?
C5 C6 H6 120.1 . . ?
C2 C6 H6 120.1 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C13 111.43(16) . . ?
N2 C8 C9 108.59(15) . . ?
C13 C8 C9 110.87(16) . . ?
N2 C8 H8 108.6 . . ?
C13 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
N4 C9 C8 110.44(16) . . ?
N4 C9 C10 116.27(16) . . ?
C8 C9 C10 109.41(15) . . ?
N4 C9 H9 106.7 . . ?
C8 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C11 C10 C9 111.13(16) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 111.42(17) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.80(16) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C8 C13 C12 110.91(17) . . ?
C8 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.0 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C8 N2 C1 N1 -169.39(18) . . . . ?
C8 N2 C1 S1 12.3(3) . . . . ?
C2 N1 C1 N2 20.8(3) . . . . ?
C2 N1 C1 S1 -160.74(18) . . . . ?
C1 N1 C2 C3 26.0(3) . . . . ?
C1 N1 C2 C6 -156.1(2) . . . . ?
C4 N3 C3 C2 -1.9(3) . . . . ?
C7 N3 C3 C2 174.30(19) . . . . ?
C6 C2 C3 N3 1.9(3) . . . . ?
N1 C2 C3 N3 179.70(18) . . . . ?
C3 N3 C4 C5 0.4(3) . . . . ?
C7 N3 C4 C5 -175.8(2) . . . . ?
N3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C2 -1.0(3) . . . . ?
C3 C2 C6 C5 -0.4(3) . . . . ?
N1 C2 C6 C5 -178.37(19) . . . . ?
C1 N2 C8 C13 -96.9(2) . . . . ?
C1 N2 C8 C9 140.71(19) . . . . ?
C14 N4 C9 C8 -66.6(2) . . . . ?
C15 N4 C9 C8 167.03(16) . . . . ?
C14 N4 C9 C10 58.9(2) . . . . ?
C15 N4 C9 C10 -67.6(2) . . . . ?
N2 C8 C9 N4 -50.2(2) . . . . ?
C13 C8 C9 N4 -172.93(15) . . . . ?
N2 C8 C9 C10 -179.40(16) . . . . ?
C13 C8 C9 C10 57.9(2) . . . . ?
N4 C9 C10 C11 177.59(16) . . . . ?
C8 C9 C10 C11 -56.5(2) . . . . ?
C9 C10 C11 C12 55.8(2) . . . . ?
C10 C11 C12 C13 -55.2(2) . . . . ?
N2 C8 C13 C12 -179.38(15) . . . . ?
C9 C8 C13 C12 -58.3(2) . . . . ?
C11 C12 C13 C8 56.4(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
_geom_hbond_publ_flag
N1 H1N I1 0.82(3) 2.87(3) 3.6677(18) 164(2) . yes
N2 H2N I1 0.89(3) 2.86(3) 3.7046(17) 159(2) 4_466 yes
C3 H3 N4 0.95 2.49 3.412(2) 162.3 . yes
C4 H4 I1 0.95 3.08 3.994(2) 160.7 1_545 yes

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.055

