# 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_full
_database_code_depnum_ccdc_archive 'CCDC 2474768'
loop_
_audit_author_name
_audit_author_address
'Asger Strandfelt'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2025-09-10 downloaded from the CCDC.
;
_audit_creation_date             2024-11-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        'Cyclohexylammonium chloride'
_chemical_formula_moiety         'Cl, C6 H14 N'
_chemical_formula_sum            'C6 H14 Cl N'
_chemical_formula_weight         135.63
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 '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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.220(3)
_cell_length_b                   11.185(4)
_cell_length_c                   7.437(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     766.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    391
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      3.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0864 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.8500.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             296
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0944
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6473
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         1.821
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                1153
_reflns_number_total             1564
_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       ?
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1564
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.018
_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)+(0.0317P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C003(H00D,H00E), C004(H00F,H00G), C005(H00H,H00I), C007(H00J,H00K), C008(H00L,
 H00M)
2.c Idealised Me refined as rotating group:
 N002(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_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
Cl01 Cl 0.54157(10) 0.13614(8) 0.1944(2) 0.0202(3) Uani 1 1 d . . . . .
N002 N 0.6224(4) 0.1057(3) 0.6045(6) 0.0184(9) Uani 1 1 d . . . . .
H00A H 0.604832 0.115271 0.484959 0.022 Uiso 1 1 calc R U . . .
H00B H 0.580669 0.036645 0.643227 0.022 Uiso 1 1 calc R U . . .
H00C H 0.719796 0.102441 0.623672 0.022 Uiso 1 1 calc R U . . .
C003 C 0.3821(5) 0.4250(4) 0.7257(8) 0.0223(14) Uani 1 1 d . . . . .
H00D H 0.342749 0.492183 0.797395 0.027 Uiso 1 1 calc R U . . .
H00E H 0.344961 0.432802 0.601360 0.027 Uiso 1 1 calc R U . . .
C004 C 0.3960(4) 0.2007(3) 0.7070(10) 0.0201(10) Uani 1 1 d . . . . .
H00F H 0.365885 0.125714 0.767185 0.024 Uiso 1 1 calc R U . . .
H00G H 0.359579 0.198666 0.581829 0.024 Uiso 1 1 calc R U . . .
C005 C 0.6122(5) 0.3250(4) 0.6235(7) 0.0207(11) Uani 1 1 d . . . . .
H00H H 0.583144 0.328339 0.495443 0.025 Uiso 1 1 calc R U . . .
H00I H 0.719367 0.328579 0.629391 0.025 Uiso 1 1 calc R U . . .
C006 C 0.5598(4) 0.2090(3) 0.7059(11) 0.0179(10) Uani 1 1 d . . . . .
H006 H 0.595073 0.205027 0.832895 0.021 Uiso 1 1 calc R U . . .
C007 C 0.3304(5) 0.3074(4) 0.8054(8) 0.0215(11) Uani 1 1 d . . . . .
H00J H 0.223344 0.303182 0.797828 0.026 Uiso 1 1 calc R U . . .
H00K H 0.357894 0.303841 0.934034 0.026 Uiso 1 1 calc R U . . .
C008 C 0.5477(5) 0.4318(4) 0.7239(8) 0.0202(14) Uani 1 1 d . . . . .
H00L H 0.584396 0.432723 0.849026 0.024 Uiso 1 1 calc R U . . .
H00M H 0.578596 0.506910 0.664799 0.024 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl01 0.0215(5) 0.0239(5) 0.0151(5) 0.0000(8) -0.0009(9) -0.0006(4)
N002 0.017(2) 0.0234(19) 0.015(2) 0.0013(17) -0.0014(18) 0.0006(16)
C003 0.022(2) 0.020(2) 0.024(4) -0.003(2) -0.003(3) 0.0004(18)
C004 0.016(2) 0.020(2) 0.024(3) 0.000(3) 0.005(3) -0.0013(16)
C005 0.019(2) 0.025(2) 0.019(3) 0.001(2) 0.001(2) -0.003(2)
C006 0.021(2) 0.0216(19) 0.011(2) -0.001(3) 0.002(3) 0.0021(16)
C007 0.018(2) 0.023(2) 0.023(3) 0.001(2) 0.002(2) 0.001(2)
C008 0.018(2) 0.022(2) 0.020(4) -0.003(2) 0.001(3) 0.0005(19)

_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
N002 H00A 0.9100 . ?
N002 H00B 0.9100 . ?
N002 H00C 0.9100 . ?
N002 C006 1.495(6) . ?
C003 H00D 0.9900 . ?
C003 H00E 0.9900 . ?
C003 C007 1.520(6) . ?
C003 C008 1.529(6) . ?
C004 H00F 0.9900 . ?
C004 H00G 0.9900 . ?
C004 C006 1.513(5) . ?
C004 C007 1.525(6) . ?
C005 H00H 0.9900 . ?
C005 H00I 0.9900 . ?
C005 C006 1.514(6) . ?
C005 C008 1.529(7) . ?
C006 H006 1.0000 . ?
C007 H00J 0.9900 . ?
C007 H00K 0.9900 . ?
C008 H00L 0.9900 . ?
C008 H00M 0.9900 . ?

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
H00A N002 H00B 109.5 . . ?
H00A N002 H00C 109.5 . . ?
H00B N002 H00C 109.5 . . ?
C006 N002 H00A 109.5 . . ?
C006 N002 H00B 109.5 . . ?
C006 N002 H00C 109.5 . . ?
H00D C003 H00E 108.0 . . ?
C007 C003 H00D 109.4 . . ?
C007 C003 H00E 109.4 . . ?
C007 C003 C008 111.1(4) . . ?
C008 C003 H00D 109.4 . . ?
C008 C003 H00E 109.4 . . ?
H00F C004 H00G 108.1 . . ?
C006 C004 H00F 109.5 . . ?
C006 C004 H00G 109.5 . . ?
C006 C004 C007 110.5(4) . . ?
C007 C004 H00F 109.5 . . ?
C007 C004 H00G 109.5 . . ?
H00H C005 H00I 108.1 . . ?
C006 C005 H00H 109.6 . . ?
C006 C005 H00I 109.6 . . ?
C006 C005 C008 110.4(4) . . ?
C008 C005 H00H 109.6 . . ?
C008 C005 H00I 109.6 . . ?
N002 C006 C004 109.9(4) . . ?
N002 C006 C005 109.6(5) . . ?
N002 C006 H006 108.4 . . ?
C004 C006 C005 111.9(4) . . ?
C004 C006 H006 108.4 . . ?
C005 C006 H006 108.4 . . ?
C003 C007 C004 111.5(4) . . ?
C003 C007 H00J 109.3 . . ?
C003 C007 H00K 109.3 . . ?
C004 C007 H00J 109.3 . . ?
C004 C007 H00K 109.3 . . ?
H00J C007 H00K 108.0 . . ?
C003 C008 C005 110.7(4) . . ?
C003 C008 H00L 109.5 . . ?
C003 C008 H00M 109.5 . . ?
C005 C008 H00L 109.5 . . ?
C005 C008 H00M 109.5 . . ?
H00L C008 H00M 108.1 . . ?

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
C006 C004 C007 C003 55.3(6) . . . . ?
C006 C005 C008 C003 -56.2(6) . . . . ?
C007 C003 C008 C005 55.8(6) . . . . ?
C007 C004 C006 N002 -178.4(5) . . . . ?
C007 C004 C006 C005 -56.4(7) . . . . ?
C008 C003 C007 C004 -55.4(6) . . . . ?
C008 C005 C006 N002 179.3(4) . . . . ?
C008 C005 C006 C004 57.1(7) . . . . ?

_shelx_res_file                  
;
TITL full_a.res in Pca2(1)
    full.res
    created by SHELXL-2019/1 at 14:24:01 on 12-Nov-2024
REM Old TITL full in Pca2(1)
REM SHELXT solution in Pca2(1): R1 0.096, Rweak 0.006, Alpha 0.004
REM <I/s> 0.277 for 99 systematic absences, Orientation as input
REM Flack x = -0.067 ( 0.144 ) from 416 Parsons' quotients
REM Formula found by SHELXT: C6 N Cl
CELL 0.71073 9.2203 11.1849 7.4365 90 90 90
ZERR 4 0.0031 0.0043 0.0034 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,0.5+Z
SFAC C H Cl N
UNIT 24 56 4 4

L.S. 4
PLAN  4
TEMP -173.15
CONF
list 4
fmap 2
MORE -1
BOND $H
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\full.hkl">
REM </olex2.extras>

WGHT    0.031700
FVAR       0.71644
CL01  3    0.541568    0.136143    0.194430    11.00000    0.02146    0.02389 =
         0.01514   -0.00002   -0.00089   -0.00064
N002  4    0.622399    0.105736    0.604517    11.00000    0.01702    0.02340 =
         0.01481    0.00132   -0.00145    0.00057
AFIX 137
H00A  2    0.604832    0.115271    0.484959    11.00000   -1.20000
H00B  2    0.580669    0.036645    0.643227    11.00000   -1.20000
H00C  2    0.719796    0.102441    0.623672    11.00000   -1.20000
AFIX   0
C003  1    0.382063    0.424996    0.725734    11.00000    0.02211    0.02038 =
         0.02437   -0.00293   -0.00319    0.00043
AFIX  23
H00D  2    0.342749    0.492183    0.797395    11.00000   -1.20000
H00E  2    0.344961    0.432802    0.601360    11.00000   -1.20000
AFIX   0
C004  1    0.395999    0.200670    0.707027    11.00000    0.01632    0.02019 =
         0.02367   -0.00013    0.00451   -0.00126
AFIX  23
H00F  2    0.365885    0.125714    0.767185    11.00000   -1.20000
H00G  2    0.359579    0.198666    0.581829    11.00000   -1.20000
AFIX   0
C005  1    0.612187    0.325007    0.623509    11.00000    0.01902    0.02452 =
         0.01868    0.00121    0.00050   -0.00301
AFIX  23
H00H  2    0.583144    0.328339    0.495443    11.00000   -1.20000
H00I  2    0.719367    0.328579    0.629391    11.00000   -1.20000
AFIX   0
C006  1    0.559807    0.208993    0.705871    11.00000    0.02072    0.02156 =
         0.01141   -0.00114    0.00165    0.00210
AFIX  13
H006  2    0.595073    0.205027    0.832895    11.00000   -1.20000
AFIX   0
C007  1    0.330420    0.307360    0.805448    11.00000    0.01794    0.02324 =
         0.02322    0.00103    0.00228    0.00106
AFIX  23
H00J  2    0.223344    0.303182    0.797828    11.00000   -1.20000
H00K  2    0.357894    0.303841    0.934034    11.00000   -1.20000
AFIX   0
C008  1    0.547675    0.431818    0.723933    11.00000    0.01844    0.02182 =
         0.02038   -0.00316    0.00084    0.00052
AFIX  23
H00L  2    0.584396    0.432723    0.849026    11.00000   -1.20000
H00M  2    0.578596    0.506910    0.664799    11.00000   -1.20000
AFIX   0
HKLF 4




REM  full_a.res in Pca2(1)
REM wR2 = 0.1055, GooF = S = 1.018, Restrained GooF = 1.018 for all data
REM R1 = 0.0458 for 1153 Fo > 4sig(Fo) and 0.0763 for all 1564 data
REM 74 parameters refined using 1 restraints

END

WGHT      0.0317      0.0000

REM Highest difference peak  0.291,  deepest hole -0.300,  1-sigma level  0.069
Q1    1   0.3866  0.1342  0.1955  11.00000  0.05    0.29
Q2    1   0.4661  0.4046  0.6943  11.00000  0.05    0.24
Q3    1   0.5232  0.0591  0.3624  11.00000  0.05    0.24
Q4    1   0.6497 -0.0162  0.8712  11.00000  0.05    0.24
;
_shelx_res_checksum              44832
_olex2_submission_special_instructions 'No special instructions were received'
