# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# 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 
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data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2181683'
_audit_update_record             
;
2022-06-24 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"ï?1/2hiral trans(+)N,N'-bis-(salicylidene)-1,2-diaminocyclohexane Schif base"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   15.7967(3)
_cell_length_b                   11.6889(2)
_cell_length_c                   9.4813(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.276(2)
_cell_angle_gamma                90
_cell_volume                     1736.59(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6011
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3190
_cell_measurement_theta_min      4.7070

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.36a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13105
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_theta_min         4.720
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_full        67.045
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             2932
_reflns_number_gt                2865
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.899
_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_cell_refinement       'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_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)+(0.0421P)²+0.4185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.28(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     223
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34119(14) 0.27854(19) 0.3179(2) 0.0198(5) Uani 1 1 d . . . . .
H1 H 0.352012 0.209058 0.265196 0.024 Uiso 1 1 calc R U . . .
C2 C 0.38375(14) 0.38102(19) 0.2539(2) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.373116 0.449951 0.307806 0.024 Uiso 1 1 calc R U . . .
C3 C 0.34581(14) 0.3980(2) 0.0989(2) 0.0236(5) Uani 1 1 d . . . . .
H3A H 0.357365 0.331027 0.044001 0.028 Uiso 1 1 calc R U . . .
H3B H 0.372454 0.463454 0.059755 0.028 Uiso 1 1 calc R U . . .
C4 C 0.24935(15) 0.4171(2) 0.0878(3) 0.0266(5) Uani 1 1 d . . . . .
H4A H 0.238162 0.488127 0.135093 0.032 Uiso 1 1 calc R U . . .
H4B H 0.226031 0.423999 -0.011502 0.032 Uiso 1 1 calc R U . . .
C5 C 0.20526(15) 0.3188(2) 0.1552(3) 0.0250(5) Uani 1 1 d . . . . .
H5A H 0.209955 0.249681 0.100066 0.030 Uiso 1 1 calc R U . . .
H5B H 0.145129 0.336342 0.153518 0.030 Uiso 1 1 calc R U . . .
C6 C 0.24493(14) 0.2981(2) 0.3087(3) 0.0242(5) Uani 1 1 d . . . . .
H6A H 0.218416 0.231812 0.346290 0.029 Uiso 1 1 calc R U . . .
H6B H 0.234064 0.363731 0.366439 0.029 Uiso 1 1 calc R U . . .
C7 C 0.41183(13) 0.16924(19) 0.5064(2) 0.0197(5) Uani 1 1 d . . . . .
H7 H 0.408111 0.108910 0.441964 0.024 Uiso 1 1 calc R U . . .
C8 C 0.45544(14) 0.15089(19) 0.6490(3) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.47039(15) 0.24260(19) 0.7458(3) 0.0215(5) Uani 1 1 d . . . . .
C10 C 0.52029(15) 0.2254(2) 0.8758(3) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.530758 0.285947 0.939151 0.029 Uiso 1 1 calc R U . . .
C11 C 0.55446(14) 0.1187(2) 0.9114(2) 0.0233(5) Uani 1 1 d . . . . .
H11 H 0.588662 0.108565 0.997780 0.028 Uiso 1 1 calc R U . . .
C12 C 0.53808(14) 0.0263(2) 0.8189(3) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.559891 -0.045758 0.844353 0.029 Uiso 1 1 calc R U . . .
C13 C 0.48907(14) 0.0430(2) 0.6891(2) 0.0212(5) Uani 1 1 d . . . . .
H13 H 0.478188 -0.018547 0.627259 0.025 Uiso 1 1 calc R U . . .
C14 C 0.52420(14) 0.42243(19) 0.3544(2) 0.0207(5) Uani 1 1 d . . . . .
H14 H 0.499261 0.475995 0.408826 0.025 Uiso 1 1 calc R U . . .
C15 C 0.61674(14) 0.41017(18) 0.3747(2) 0.0201(5) Uani 1 1 d . . . . .
C16 C 0.65800(14) 0.3311(2) 0.2945(2) 0.0218(5) Uani 1 1 d . . . . .
C17 C 0.74685(15) 0.3245(2) 0.3114(3) 0.0238(5) Uani 1 1 d . . . . .
H17 H 0.774218 0.273892 0.256507 0.029 Uiso 1 1 calc R U . . .
C18 C 0.79415(15) 0.3940(2) 0.4106(3) 0.0255(5) Uani 1 1 d . . . . .
H18 H 0.853406 0.389642 0.421577 0.031 Uiso 1 1 calc R U . . .
C19 C 0.75434(15) 0.4701(2) 0.4941(3) 0.0262(5) Uani 1 1 d . . . . .
H19 H 0.786620 0.514824 0.562072 0.031 Uiso 1 1 calc R U . . .
C20 C 0.66624(14) 0.4785(2) 0.4749(3) 0.0245(5) Uani 1 1 d . . . . .
H20 H 0.639506 0.530151 0.529348 0.029 Uiso 1 1 calc R U . . .
N1 N 0.37828(11) 0.26570(16) 0.4662(2) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.47592(12) 0.36219(16) 0.2644(2) 0.0208(4) Uani 1 1 d . . . . .
O1 O 0.43774(12) 0.34759(13) 0.71466(19) 0.0287(4) Uani 1 1 d D . . . .
O2 O 0.61291(11) 0.26135(15) 0.19885(18) 0.0279(4) Uani 1 1 d D . . . .
H111 H 0.4100(19) 0.346(3) 0.633(2) 0.042 Uiso 1 1 d D U . . .
H211 H 0.5617(10) 0.277(3) 0.197(3) 0.042 Uiso 1 1 d D 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
C1 N1 1.461(3) . ?
C1 C6 1.529(3) . ?
C1 C2 1.536(3) . ?
C1 H1 0.9800 . ?
C2 N2 1.463(3) . ?
C2 C3 1.528(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.529(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.283(3) . ?
C7 C8 1.453(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.403(3) . ?
C8 C9 1.412(3) . ?
C9 O1 1.349(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.281(3) . ?
C14 C15 1.457(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.401(3) . ?
C15 C16 1.408(3) . ?
C16 O2 1.353(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O1 H111 0.842(14) . ?
O2 H211 0.828(14) . ?

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
N1 C1 C6 110.18(18) . . ?
N1 C1 C2 108.56(17) . . ?
C6 C1 C2 110.03(18) . . ?
N1 C1 H1 109.3 . . ?
C6 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
N2 C2 C3 110.54(18) . . ?
N2 C2 C1 109.71(17) . . ?
C3 C2 C1 110.08(18) . . ?
N2 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C2 C3 C4 110.56(19) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.35(19) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.3(2) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C1 111.26(19) . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C8 122.4(2) . . ?
N1 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 C7 120.3(2) . . ?
C9 C8 C7 120.89(19) . . ?
O1 C9 C10 118.9(2) . . ?
O1 C9 C8 121.4(2) . . ?
C10 C9 C8 119.7(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
N2 C14 C15 122.5(2) . . ?
N2 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C20 C15 C16 118.9(2) . . ?
C20 C15 C14 119.9(2) . . ?
C16 C15 C14 121.23(19) . . ?
O2 C16 C17 118.7(2) . . ?
O2 C16 C15 121.14(19) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.3(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C15 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C7 N1 C1 118.43(19) . . ?
C14 N2 C2 117.79(19) . . ?
C9 O1 H111 109(2) . . ?
C16 O2 H211 108(2) . . ?

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 C1 C2 N2 58.8(2) . . . . ?
C6 C1 C2 N2 179.41(18) . . . . ?
N1 C1 C2 C3 -179.38(17) . . . . ?
C6 C1 C2 C3 -58.7(2) . . . . ?
N2 C2 C3 C4 179.76(18) . . . . ?
C1 C2 C3 C4 58.4(2) . . . . ?
C2 C3 C4 C5 -56.3(3) . . . . ?
C3 C4 C5 C6 54.4(3) . . . . ?
C4 C5 C6 C1 -55.0(3) . . . . ?
N1 C1 C6 C5 176.70(19) . . . . ?
C2 C1 C6 C5 57.0(2) . . . . ?
N1 C7 C8 C13 178.2(2) . . . . ?
N1 C7 C8 C9 -6.5(3) . . . . ?
C13 C8 C9 O1 -178.2(2) . . . . ?
C7 C8 C9 O1 6.5(3) . . . . ?
C13 C8 C9 C10 2.3(3) . . . . ?
C7 C8 C9 C10 -173.0(2) . . . . ?
O1 C9 C10 C11 179.7(2) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C9 C8 C13 C12 -1.9(3) . . . . ?
C7 C8 C13 C12 173.5(2) . . . . ?
N2 C14 C15 C20 -179.9(2) . . . . ?
N2 C14 C15 C16 0.5(3) . . . . ?
C20 C15 C16 O2 178.4(2) . . . . ?
C14 C15 C16 O2 -2.1(3) . . . . ?
C20 C15 C16 C17 -2.4(3) . . . . ?
C14 C15 C16 C17 177.2(2) . . . . ?
O2 C16 C17 C18 -178.9(2) . . . . ?
C15 C16 C17 C18 1.9(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
C18 C19 C20 C15 1.1(4) . . . . ?
C16 C15 C20 C19 0.9(3) . . . . ?
C14 C15 C20 C19 -178.7(2) . . . . ?
C8 C7 N1 C1 175.63(19) . . . . ?
C6 C1 N1 C7 115.4(2) . . . . ?
C2 C1 N1 C7 -124.0(2) . . . . ?
C15 C14 N2 C2 179.46(19) . . . . ?
C3 C2 N2 C14 130.1(2) . . . . ?
C1 C2 N2 C14 -108.3(2) . . . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034

