# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_AI1171
_database_code_depnum_ccdc_archive 'CCDC 2375096'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University 
Canada
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-10-03 downloaded from the CCDC.
;
_audit_creation_date             2024-06-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
'4-(tert-butyl)-4λ4-azaspiro[2.5]octane hydrochloride'
_chemical_formula_moiety         'Cl, C11 H22 N'
_chemical_formula_sum            'C11 H22 Cl N'
_chemical_formula_weight         203.74
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2410(3)
_cell_length_b                   15.6585(7)
_cell_length_c                   9.0543(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.0640(10)
_cell_angle_gamma                90
_cell_volume                     1167.62(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2140
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.598
_cell_measurement_theta_min      6.071
_shelx_estimated_absorpt_T_max   0.612
_shelx_estimated_absorpt_T_min   0.237
_exptl_absorpt_coefficient_mu    2.541
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.796
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.214
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18713
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.598
_diffrn_reflns_theta_min         6.071
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2140
_reflns_number_total             2268
_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       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²+0.2526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1348
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Riding coordinates:
 N1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5AB), C4(H4A,H4AB), C3(H3A,H3AB), C6(H6A,H6AB), C11(H11A,H11B),
 C12(H12A,H12B)
1.c Idealised Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.26403(5) 0.60868(3) 0.30734(4) 0.0561(2) Uani 1 1 d . . . . .
N1 N 0.31283(14) 0.61285(7) 0.65396(14) 0.0360(3) Uani 1 1 d . . . . .
H1 H 0.297390 0.620200 0.546806 0.054 Uiso 1 1 d R U . . .
C2 C 0.15029(18) 0.62409(10) 0.72017(18) 0.0426(4) Uani 1 1 d . . . . .
C5 C 0.3425(2) 0.48124(11) 0.8200(2) 0.0568(5) Uani 1 1 d . . . . .
H5A H 0.354661 0.419754 0.813540 0.068 Uiso 1 1 calc R U . . .
H5AB H 0.430307 0.502704 0.883968 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1820(3) 0.50122(13) 0.8897(2) 0.0666(5) Uani 1 1 d . . . . .
H4A H 0.187113 0.484087 0.992709 0.080 Uiso 1 1 calc R U . . .
H4AB H 0.095733 0.469067 0.839712 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1449(2) 0.59616(12) 0.8788(2) 0.0559(5) Uani 1 1 d . . . . .
H3A H 0.038092 0.607418 0.916083 0.067 Uiso 1 1 calc R U . . .
H3AB H 0.224003 0.628106 0.938319 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3802(3) 0.76549(12) 0.7161(3) 0.0771(7) Uani 1 1 d . . . . .
H8A H 0.464893 0.804572 0.746087 0.116 Uiso 1 1 calc R U . . .
H8B H 0.299856 0.763701 0.790150 0.116 Uiso 1 1 calc R U . . .
H8C H 0.330753 0.784163 0.624023 0.116 Uiso 1 1 calc R U . . .
C7 C 0.45127(18) 0.67749(9) 0.69703(17) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.35807(19) 0.51938(9) 0.66700(17) 0.0441(4) Uani 1 1 d . . . . .
H6A H 0.469408 0.512581 0.637746 0.053 Uiso 1 1 calc R U . . .
H6AB H 0.289540 0.487092 0.597870 0.053 Uiso 1 1 calc R U . . .
C9 C 0.5672(2) 0.67838(15) 0.5693(2) 0.0675(5) Uani 1 1 d . . . . .
H9A H 0.614667 0.622812 0.559095 0.101 Uiso 1 1 calc R U . . .
H9B H 0.651361 0.719637 0.589011 0.101 Uiso 1 1 calc R U . . .
H9C H 0.508376 0.693258 0.479529 0.101 Uiso 1 1 calc R U . . .
C10 C 0.5500(3) 0.65141(15) 0.8358(2) 0.0684(6) Uani 1 1 d . . . . .
H10A H 0.598360 0.596478 0.820672 0.103 Uiso 1 1 calc R U . . .
H10B H 0.479878 0.648515 0.918104 0.103 Uiso 1 1 calc R U . . .
H10C H 0.633742 0.692849 0.855970 0.103 Uiso 1 1 calc R U . . .
C11 C 0.0387(2) 0.69093(12) 0.6571(2) 0.0596(5) Uani 1 1 d . . . . .
H11A H 0.079141 0.727408 0.580027 0.071 Uiso 1 1 calc R U . . .
H11B H -0.034557 0.718657 0.723521 0.071 Uiso 1 1 calc R U . . .
C12 C 0.0082(2) 0.59883(12) 0.6202(2) 0.0582(5) Uani 1 1 d . . . . .
H12A H 0.030588 0.579725 0.521088 0.070 Uiso 1 1 calc R U . . .
H12B H -0.083181 0.570969 0.664672 0.070 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
N1 H1 0.9808 . ?
N1 C2 1.497(2) . ?
N1 C7 1.5640(18) . ?
N1 C6 1.5139(17) . ?
C2 C3 1.503(2) . ?
C2 C11 1.493(2) . ?
C2 C12 1.507(2) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C5 C4 1.518(3) . ?
C5 C6 1.519(2) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C4 C3 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C7 1.509(2) . ?
C7 C9 1.526(2) . ?
C7 C10 1.528(2) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.500(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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 H1 107.2 . . ?
C2 N1 C7 118.63(11) . . ?
C2 N1 C6 107.68(11) . . ?
C7 N1 H1 103.8 . . ?
C6 N1 H1 102.3 . . ?
C6 N1 C7 115.52(11) . . ?
N1 C2 C3 113.95(14) . . ?
N1 C2 C12 114.57(14) . . ?
C3 C2 C12 116.62(15) . . ?
C11 C2 N1 118.47(14) . . ?
C11 C2 C3 122.02(14) . . ?
C11 C2 C12 59.98(12) . . ?
H5A C5 H5AB 107.7 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5AB 108.8 . . ?
C4 C5 C6 113.66(15) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5AB 108.8 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4AB 109.5 . . ?
C5 C4 C3 110.54(14) . . ?
H4A C4 H4AB 108.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4AB 109.5 . . ?
C2 C3 C4 109.50(15) . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3AB 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3AB 109.8 . . ?
H3A C3 H3AB 108.2 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
C8 C7 N1 109.68(13) . . ?
C8 C7 C9 109.52(16) . . ?
C8 C7 C10 110.32(17) . . ?
C9 C7 N1 106.73(13) . . ?
C9 C7 C10 107.24(15) . . ?
C10 C7 N1 113.21(13) . . ?
N1 C6 C5 115.01(12) . . ?
N1 C6 H6A 108.5 . . ?
N1 C6 H6AB 108.5 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6AB 108.5 . . ?
H6A C6 H6AB 107.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 117.7 . . ?
C2 C11 H11B 117.7 . . ?
C2 C11 C12 60.48(12) . . ?
H11A C11 H11B 114.8 . . ?
C12 C11 H11A 117.7 . . ?
C12 C11 H11B 117.7 . . ?
C2 C12 H12A 117.8 . . ?
C2 C12 H12B 117.8 . . ?
C11 C12 C2 59.54(11) . . ?
C11 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 115.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AI1178
_database_code_depnum_ccdc_archive 'CCDC 2375097'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University 
Canada
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-10-03 downloaded from the CCDC.
;
_audit_creation_date             2024-06-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
4,9-dibenzyl-4,9-diazadispiro[2.2.26.23]decane
_chemical_formula_moiety         'C22 H26 N2'
_chemical_formula_sum            'C22 H26 N2'
_chemical_formula_weight         318.45
_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 0.0181 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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   16.1970(5)
_cell_length_b                   5.7050(2)
_cell_length_c                   20.8080(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.3740(10)
_cell_angle_gamma                90
_cell_volume                     1802.45(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1498
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.660
_cell_measurement_theta_min      6.012
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.063
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14634
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.660
_diffrn_reflns_theta_min         6.012
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '/w and /f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1498
_reflns_number_total             1767
_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       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.0081(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.037
_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)+(0.0481P)²+0.8605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3AB), C4(H4A,H4AB), C11(H11A,H11B), C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.32804(6) 0.22326(18) 0.47887(5) 0.0418(3) Uani 1 1 d . . . . .
C2 C 0.33378(8) 0.2258(2) 0.55017(6) 0.0423(3) Uani 1 1 d . . . . .
C3 C 0.23946(7) 0.1433(2) 0.43608(6) 0.0432(3) Uani 1 1 d . . . . .
H3A H 0.234070 -0.022411 0.444257 0.052 Uiso 1 1 calc R U . . .
H3AB H 0.232710 0.162378 0.388191 0.052 Uiso 1 1 calc R U . . .
C4 C 0.35262(8) 0.4499(2) 0.45704(7) 0.0483(4) Uani 1 1 d . . . . .
H4A H 0.407926 0.501750 0.490534 0.058 Uiso 1 1 calc R U . . .
H4AB H 0.308031 0.565324 0.455594 0.058 Uiso 1 1 calc R U . . .
C6 C 0.40680(9) 0.2520(3) 0.37102(8) 0.0554(4) Uani 1 1 d . . . . .
H6 H 0.429913 0.133007 0.402763 0.067 Uiso 1 1 calc R U . . .
C5 C 0.36208(8) 0.4364(2) 0.38749(7) 0.0456(3) Uani 1 1 d . . . . .
C8 C 0.38361(10) 0.4173(3) 0.26051(8) 0.0613(4) Uani 1 1 d . . . . .
H8 H 0.390771 0.410538 0.218100 0.074 Uiso 1 1 calc R U . . .
C7 C 0.41741(11) 0.2429(3) 0.30808(8) 0.0618(4) Uani 1 1 d . . . . .
H7 H 0.447588 0.118089 0.297763 0.074 Uiso 1 1 calc R U . . .
C10 C 0.32852(9) 0.6107(2) 0.33928(7) 0.0555(4) Uani 1 1 d . . . . .
H10 H 0.298359 0.735831 0.349441 0.067 Uiso 1 1 calc R U . . .
C11 C 0.42493(9) 0.2279(3) 0.60223(7) 0.0578(4) Uani 1 1 d . . . . .
H11A H 0.434446 0.313440 0.644495 0.069 Uiso 1 1 calc R U . . .
H11B H 0.473931 0.231722 0.585610 0.069 Uiso 1 1 calc R U . . .
C12 C 0.37070(9) 0.0073(3) 0.59062(7) 0.0555(4) Uani 1 1 d . . . . .
H12A H 0.347483 -0.039418 0.625821 0.067 Uiso 1 1 calc R U . . .
H12B H 0.386985 -0.121171 0.566911 0.067 Uiso 1 1 calc R U . . .
C9 C 0.33910(10) 0.6019(3) 0.27606(8) 0.0637(4) Uani 1 1 d . . . . .
H9 H 0.316175 0.720539 0.244167 0.076 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
N1 C2 1.4539(15) . ?
N1 C3 1.4730(15) . ?
N1 C4 1.4706(16) . ?
C2 C3 1.5109(16) 7_556 ?
C2 C11 1.4966(17) . ?
C2 C12 1.5063(18) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C4 C5 1.5094(17) . ?
C6 H6 0.9300 . ?
C6 C5 1.3865(18) . ?
C6 C7 1.380(2) . ?
C5 C10 1.3821(19) . ?
C8 H8 0.9300 . ?
C8 C7 1.376(2) . ?
C8 C9 1.377(2) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.385(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.505(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9 0.9300 . ?

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 C3 108.82(9) . . ?
C2 N1 C4 112.24(9) . . ?
C4 N1 C3 113.39(10) . . ?
N1 C2 C3 115.00(10) . 7_556 ?
N1 C2 C11 115.79(11) . . ?
N1 C2 C12 115.71(11) . . ?
C11 C2 C3 120.05(11) . 7_556 ?
C11 C2 C12 60.17(9) . . ?
C12 C2 C3 119.23(11) . 7_556 ?
N1 C3 C2 113.34(10) . 7_556 ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3AB 108.9 . . ?
C2 C3 H3A 108.9 7_556 . ?
C2 C3 H3AB 108.9 7_556 . ?
H3A C3 H3AB 107.7 . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4AB 109.1 . . ?
N1 C4 C5 112.35(10) . . ?
H4A C4 H4AB 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4AB 109.1 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.76(13) . . ?
C6 C5 C4 120.78(12) . . ?
C10 C5 C4 120.92(12) . . ?
C10 C5 C6 118.28(12) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.59(14) . . ?
C9 C8 H8 120.2 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.39(14) . . ?
C8 C7 H7 119.8 . . ?
C5 C10 H10 119.5 . . ?
C5 C10 C9 121.04(13) . . ?
C9 C10 H10 119.5 . . ?
C2 C11 H11A 117.7 . . ?
C2 C11 H11B 117.7 . . ?
C2 C11 C12 60.23(8) . . ?
H11A C11 H11B 114.9 . . ?
C12 C11 H11A 117.7 . . ?
C12 C11 H11B 117.7 . . ?
C2 C12 H12A 117.8 . . ?
C2 C12 H12B 117.8 . . ?
C11 C12 C2 59.60(9) . . ?
C11 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C8 C9 C10 119.92(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AI11106
_database_code_depnum_ccdc_archive 'CCDC 2375098'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University 
Canada
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-10-03 downloaded from the CCDC.
;
_audit_creation_date             2024-07-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
'4,7-dibenzyl-4,7-diazaspiro[2.5]octane-4,7-diium di-4-methylbenzenesulfonate hydrate'
_chemical_formula_moiety         'C20 H26 N2, H2 O, 2(C7 H7 O3 S)'
_chemical_formula_sum            'C34 H42 N2 O7 S2'
_chemical_formula_weight         654.81
_chemical_absolute_configuration rm
_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 0.0181 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'
S S 0.3331 0.5567 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.120(3)
_cell_length_b                   9.381(2)
_cell_length_c                   14.431(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.580(14)
_cell_angle_gamma                90
_cell_volume                     1678.5(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4842
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.411
_cell_measurement_theta_min      3.488
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.380
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.053
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1585
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.411
_diffrn_reflns_theta_min         3.488
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4842
_reflns_number_total             6534
_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       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(12)
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6534
_refine_ls_number_restraints     394
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.027
_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)+(0.0666P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1453
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
S1A \\sim O0AA \\sim O2AA \\sim O1AA: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
S1A \\sim O4A \\sim O3A \\sim O2A: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C11A) \\sim Ueq, Uanis(O1W) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1W) = Uanis(O2W)
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(O0AA)=Sof(O1AA)=Sof(O2AA)=1-FVAR(1)
 Sof(O2A)=Sof(O3A)=Sof(O4A)=FVAR(1)
 Sof(O2W)=Sof(H2WA)=Sof(H2WB)=1-FVAR(2)
 Sof(O1W)=Sof(H1WA)=Sof(H1WB)=FVAR(2)
4.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
4.b Ternary CH refined with riding coordinates:
 N1(H1), N4(H4)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C5(H5A,H5B), C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B),
 C16(H16A,H16B)
4.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C6A(H6AA), C7A(H7AA), C6B(H6BA), C7B(H7BA),
 C9A(H9AA), C10A(H10A), C9B(H9BA), C10B(H10B)
4.e Idealised Me refined with riding coordinates:
 C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.4935(3) 0.3270(4) 0.6951(3) 0.0445(8) Uani 1 1 d . . . . .
H1 H 0.537983 0.407996 0.735463 0.053 Uiso 1 1 calc R U . . .
C2 C 0.3837(3) 0.3514(4) 0.6829(3) 0.0434(9) Uani 1 1 d . . . . .
C3 C 0.3037(4) 0.2457(5) 0.6108(3) 0.0461(9) Uani 1 1 d . . . . .
H3A H 0.234075 0.264023 0.606416 0.055 Uiso 1 1 calc R U . . .
H3B H 0.326274 0.150462 0.638852 0.055 Uiso 1 1 calc R U . . .
N4 N 0.2937(3) 0.2546(4) 0.5029(3) 0.0465(8) Uani 1 1 d . . . . .
H4 H 0.268630 0.350595 0.475265 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4855(4) 0.3351(5) 0.5879(3) 0.0512(10) Uani 1 1 d . . . . .
H6A H 0.555417 0.313916 0.593859 0.061 Uiso 1 1 calc R U . . .
H6B H 0.466188 0.431549 0.561119 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4034(4) 0.2334(5) 0.5110(4) 0.0528(10) Uani 1 1 d . . . . .
H5A H 0.427209 0.136355 0.533266 0.063 Uiso 1 1 calc R U . . .
H5B H 0.398033 0.246931 0.442020 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5506(4) 0.1930(5) 0.7559(4) 0.0556(11) Uani 1 1 d . . . . .
H9A H 0.510456 0.109784 0.717133 0.067 Uiso 1 1 calc R U . . .
H9B H 0.621881 0.188173 0.761822 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3509(5) 0.5027(5) 0.6798(4) 0.0616(13) Uani 1 1 d . . . . .
H8A H 0.276224 0.527272 0.632548 0.074 Uiso 1 1 calc R U . . .
H8B H 0.402812 0.575957 0.688028 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3744(4) 0.4112(5) 0.7738(3) 0.0576(12) Uani 1 1 d . . . . .
H7A H 0.440474 0.429266 0.838664 0.069 Uiso 1 1 calc R U . . .
H7B H 0.313878 0.380578 0.783180 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5607(4) 0.1910(5) 0.8636(4) 0.0558(11) Uani 1 1 d . . . . .
C11 C 0.6427(5) 0.2676(6) 0.9448(4) 0.0684(14) Uani 1 1 d . . . . .
H11 H 0.694480 0.313228 0.933100 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6480(6) 0.2766(7) 1.0430(4) 0.0878(19) Uani 1 1 d . . . . .
H12 H 0.703427 0.327019 1.097441 0.105 Uiso 1 1 calc R U . . .
C13 C 0.5697(7) 0.2097(7) 1.0591(5) 0.097(2) Uani 1 1 d . . . . .
H13 H 0.570938 0.219276 1.123803 0.116 Uiso 1 1 calc R U . . .
C14 C 0.4918(7) 0.1309(7) 0.9824(5) 0.0882(18) Uani 1 1 d . . . . .
H14 H 0.441002 0.084065 0.995063 0.106 Uiso 1 1 calc R U . . .
C17 C 0.1025(4) 0.1702(5) 0.4141(3) 0.0551(11) Uani 1 1 d . . . . .
C16 C 0.2127(4) 0.1480(5) 0.4268(4) 0.0580(11) Uani 1 1 d . . . . .
H16A H 0.209826 0.156991 0.358496 0.070 Uiso 1 1 calc R U . . .
H16B H 0.236718 0.052159 0.452535 0.070 Uiso 1 1 calc R U . . .
C15 C 0.4875(5) 0.1200(6) 0.8847(5) 0.0703(14) Uani 1 1 d . . . . .
H15 H 0.434476 0.063889 0.832531 0.084 Uiso 1 1 calc R U . . .
C18 C 0.0345(5) 0.2709(6) 0.3436(4) 0.0695(14) Uani 1 1 d . . . . .
H18 H 0.056456 0.321308 0.301690 0.083 Uiso 1 1 calc R U . . .
C19 C -0.0673(6) 0.2977(8) 0.3347(6) 0.0920(19) Uani 1 1 d . . . . .
H19 H -0.112550 0.366032 0.287686 0.110 Uiso 1 1 calc R U . . .
C20 C -0.0992(6) 0.2217(8) 0.3962(7) 0.097(2) Uani 1 1 d . . . . .
H20 H -0.165845 0.240481 0.391833 0.116 Uiso 1 1 calc R U . . .
O1W O 0.3767(12) 0.9028(10) 0.6438(12) 0.101(4) Uani 0.74(3) 1 d G U P A 1
H1WA H 0.433622 0.854228 0.679452 0.152 Uiso 0.74(3) 1 d G U P A 1
H1WB H 0.333458 0.845164 0.597437 0.152 Uiso 0.74(3) 1 d G U P A 1
O2W O 0.406(3) 0.914(3) 0.611(3) 0.101(4) Uani 0.26(3) 1 d G . P A 2
H2WA H 0.455464 0.859548 0.654099 0.152 Uiso 0.26(3) 1 d G U P A 2
H2WB H 0.366570 0.859632 0.559174 0.152 Uiso 0.26(3) 1 d G U P A 2
S1B S 0.25579(10) 0.63620(12) 0.40614(9) 0.0554(3) Uani 1 1 d . . . . .
S1A S 0.66149(11) 0.67761(14) 0.80595(9) 0.0638(4) Uani 1 1 d . U . . .
C21 C -0.0346(6) 0.1194(8) 0.4634(5) 0.0902(19) Uani 1 1 d . . . . .
H21 H -0.058125 0.066555 0.503049 0.108 Uiso 1 1 calc R U . . .
C22 C 0.0663(5) 0.0940(7) 0.4730(4) 0.0749(16) Uani 1 1 d . . . . .
H22 H 0.110394 0.024487 0.519664 0.090 Uiso 1 1 calc R U . . .
O2A O 0.7314(15) 0.707(2) 0.7637(10) 0.101(5) Uani 0.66(3) 1 d . U P B 1
O3A O 0.5658(14) 0.763(2) 0.7604(11) 0.122(6) Uani 0.66(3) 1 d . U P B 1
O2B O 0.2401(4) 0.7649(4) 0.4509(3) 0.0921(15) Uani 1 1 d . . . . .
O4A O 0.6368(16) 0.5269(13) 0.8026(8) 0.091(4) Uani 0.66(3) 1 d . U P B 1
O3B O 0.3668(3) 0.6048(5) 0.4374(3) 0.0854(13) Uani 1 1 d . . . . .
C5A C 0.7339(4) 0.7214(5) 0.9408(4) 0.0535(11) Uani 1 1 d . . . . .
O4B O 0.2023(3) 0.5156(4) 0.4237(3) 0.0635(9) Uani 1 1 d . . . . .
C6A C 0.8108(4) 0.6282(6) 1.0115(4) 0.0689(14) Uani 1 1 d . . . . .
H6AA H 0.822497 0.540923 0.988064 0.083 Uiso 1 1 calc R U . . .
C5B C 0.1904(4) 0.6629(5) 0.2678(4) 0.0510(10) Uani 1 1 d . . . . .
C7A C 0.8700(5) 0.6650(8) 1.1169(4) 0.0807(17) Uani 1 1 d . . . . .
H7AA H 0.921251 0.601326 1.163336 0.097 Uiso 1 1 calc R U . . .
C6B C 0.1576(4) 0.7967(5) 0.2249(4) 0.0602(12) Uani 1 1 d . . . . .
H6BA H 0.168041 0.874752 0.268483 0.072 Uiso 1 1 calc R U . . .
C8A C 0.8554(5) 0.7933(7) 1.1551(5) 0.0747(15) Uani 1 1 d . . . . .
C7B C 0.1093(5) 0.8144(6) 0.1173(4) 0.0676(14) Uani 1 1 d . . . . .
H7BA H 0.088032 0.905307 0.089300 0.081 Uiso 1 1 calc R U . . .
C9A C 0.7782(5) 0.8828(6) 1.0836(5) 0.0737(15) Uani 1 1 d . . . . .
H9AA H 0.765603 0.969298 1.107326 0.088 Uiso 1 1 calc R U . . .
C8B C 0.0917(4) 0.7022(6) 0.0501(4) 0.0655(13) Uani 1 1 d . . . . .
C10A C 0.7187(5) 0.8496(6) 0.9783(4) 0.0658(13) Uani 1 1 d . . . . .
H10A H 0.667970 0.914008 0.932205 0.079 Uiso 1 1 calc R U . . .
C9B C 0.1263(5) 0.5683(6) 0.0944(4) 0.0651(13) Uani 1 1 d . . . . .
H9BA H 0.116246 0.490638 0.050589 0.078 Uiso 1 1 calc R U . . .
C11A C 0.9232(6) 0.8315(12) 1.2700(5) 0.113(3) Uani 1 1 d . U . . .
H11A H 0.917363 0.931876 1.279127 0.169 Uiso 1 1 calc R U . . .
H11B H 0.997193 0.807617 1.292577 0.169 Uiso 1 1 calc R U . . .
H11C H 0.898231 0.779283 1.311307 0.169 Uiso 1 1 calc R U . . .
C11B C 0.0380(6) 0.7227(8) -0.0681(5) 0.091(2) Uani 1 1 d . . . . .
H11D H -0.028016 0.669200 -0.100789 0.137 Uiso 1 1 calc R U . . .
H11E H 0.085265 0.689900 -0.094093 0.137 Uiso 1 1 calc R U . . .
H11F H 0.022512 0.821979 -0.084446 0.137 Uiso 1 1 calc R U . . .
C10B C 0.1751(4) 0.5481(5) 0.2020(4) 0.0585(12) Uani 1 1 d . . . . .
H10B H 0.197723 0.457541 0.230223 0.070 Uiso 1 1 calc R U . . .
O0AA O 0.589(2) 0.575(3) 0.8021(15) 0.072(6) Uani 0.34(3) 1 d . U P B 2
O1AA O 0.609(2) 0.802(2) 0.7502(18) 0.095(7) Uani 0.34(3) 1 d . U P B 2
O2AA O 0.7404(19) 0.629(4) 0.7762(16) 0.090(7) Uani 0.34(3) 1 d . 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 H1 0.9800 . ?
N1 C2 1.493(5) . ?
N1 C6 1.497(5) . ?
N1 C9 1.524(6) . ?
C2 C3 1.489(6) . ?
C2 C8 1.487(6) . ?
C2 C7 1.488(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 N4 1.497(5) . ?
N4 H4 0.9800 . ?
N4 C5 1.510(6) . ?
N4 C16 1.520(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.502(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.491(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.502(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 C11 1.389(7) . ?
C10 C15 1.381(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.348(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(8) . ?
C17 C16 1.493(7) . ?
C17 C18 1.384(8) . ?
C17 C22 1.381(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.403(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.359(10) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8501 . ?
O2W H2WB 0.8501 . ?
S1B O2B 1.436(4) . ?
S1B O3B 1.439(4) . ?
S1B O4B 1.448(3) . ?
S1B C5B 1.771(5) . ?
S1A O2A 1.413(12) . ?
S1A O3A 1.429(10) . ?
S1A O4A 1.451(9) . ?
S1A C5A 1.760(5) . ?
S1A O0AA 1.392(15) . ?
S1A O1AA 1.41(2) . ?
S1A O2AA 1.446(19) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(9) . ?
C22 H22 0.9300 . ?
C5A C6A 1.388(7) . ?
C5A C10A 1.377(7) . ?
C6A H6AA 0.9300 . ?
C6A C7A 1.384(7) . ?
C5B C6B 1.378(7) . ?
C5B C10B 1.384(7) . ?
C7A H7AA 0.9300 . ?
C7A C8A 1.380(9) . ?
C6B H6BA 0.9300 . ?
C6B C7B 1.374(7) . ?
C8A C9A 1.372(9) . ?
C8A C11A 1.508(8) . ?
C7B H7BA 0.9300 . ?
C7B C8B 1.371(8) . ?
C9A H9AA 0.9300 . ?
C9A C10A 1.375(8) . ?
C8B C9B 1.388(8) . ?
C8B C11B 1.512(7) . ?
C10A H10A 0.9300 . ?
C9B H9BA 0.9300 . ?
C9B C10B 1.377(7) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C10B H10B 0.9300 . ?

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 H1 106.6 . . ?
C2 N1 C6 108.0(3) . . ?
C2 N1 C9 115.3(3) . . ?
C6 N1 H1 106.6 . . ?
C6 N1 C9 113.3(3) . . ?
C9 N1 H1 106.6 . . ?
C3 C2 N1 112.2(3) . . ?
C8 C2 N1 116.1(4) . . ?
C8 C2 C3 119.5(4) . . ?
C8 C2 C7 60.7(3) . . ?
C7 C2 N1 118.6(4) . . ?
C7 C2 C3 120.7(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 N4 110.7(3) . . ?
H3A C3 H3B 108.1 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
C3 N4 H4 108.1 . . ?
C3 N4 C5 109.2(3) . . ?
C3 N4 C16 112.3(3) . . ?
C5 N4 H4 108.1 . . ?
C5 N4 C16 111.0(3) . . ?
C16 N4 H4 108.1 . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
N1 C6 C5 112.4(4) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
N4 C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
C6 C5 N4 112.0(4) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 N1 111.8(4) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C2 C8 H8A 117.8 . . ?
C2 C8 H8B 117.8 . . ?
C2 C8 C7 59.7(3) . . ?
H8A C8 H8B 114.9 . . ?
C7 C8 H8A 117.8 . . ?
C7 C8 H8B 117.8 . . ?
C2 C7 C8 59.6(3) . . ?
C2 C7 H7A 117.8 . . ?
C2 C7 H7B 117.8 . . ?
C8 C7 H7A 117.8 . . ?
C8 C7 H7B 117.8 . . ?
H7A C7 H7B 114.9 . . ?
C11 C10 C9 119.9(5) . . ?
C15 C10 C9 121.8(5) . . ?
C15 C10 C11 118.2(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(6) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(6) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(7) . . ?
C15 C14 H14 120.1 . . ?
C18 C17 C16 120.1(5) . . ?
C22 C17 C16 121.5(5) . . ?
C22 C17 C18 118.4(5) . . ?
N4 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
C17 C16 N4 112.1(4) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C10 C15 C14 121.1(6) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(6) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.1(7) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.9(7) . . ?
C21 C20 H20 119.6 . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?
O2B S1B O3B 114.2(3) . . ?
O2B S1B O4B 111.9(3) . . ?
O2B S1B C5B 106.2(2) . . ?
O3B S1B O4B 111.5(2) . . ?
O3B S1B C5B 106.6(2) . . ?
O4B S1B C5B 105.8(2) . . ?
O2A S1A O3A 113.3(8) . . ?
O2A S1A O4A 112.4(7) . . ?
O2A S1A C5A 106.0(5) . . ?
O3A S1A O4A 111.6(7) . . ?
O3A S1A C5A 107.4(6) . . ?
O4A S1A C5A 105.5(4) . . ?
O0AA S1A C5A 103.5(8) . . ?
O0AA S1A O1AA 111.9(11) . . ?
O0AA S1A O2AA 115.4(12) . . ?
O1AA S1A C5A 107.9(10) . . ?
O1AA S1A O2AA 111.1(14) . . ?
O2AA S1A C5A 106.2(9) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(7) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 121.0(6) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C6A C5A S1A 120.1(4) . . ?
C10A C5A S1A 121.4(4) . . ?
C10A C5A C6A 118.4(5) . . ?
C5A C6A H6AA 120.0 . . ?
C7A C6A C5A 120.0(5) . . ?
C7A C6A H6AA 120.0 . . ?
C6B C5B S1B 121.2(4) . . ?
C6B C5B C10B 119.4(4) . . ?
C10B C5B S1B 119.3(3) . . ?
C6A C7A H7AA 119.0 . . ?
C8A C7A C6A 122.0(6) . . ?
C8A C7A H7AA 119.0 . . ?
C5B C6B H6BA 120.1 . . ?
C7B C6B C5B 119.8(5) . . ?
C7B C6B H6BA 120.1 . . ?
C7A C8A C11A 120.6(7) . . ?
C9A C8A C7A 116.8(5) . . ?
C9A C8A C11A 122.6(6) . . ?
C6B C7B H7BA 119.0 . . ?
C8B C7B C6B 122.0(5) . . ?
C8B C7B H7BA 119.0 . . ?
C8A C9A H9AA 118.7 . . ?
C8A C9A C10A 122.5(5) . . ?
C10A C9A H9AA 118.7 . . ?
C7B C8B C9B 117.7(4) . . ?
C7B C8B C11B 121.6(5) . . ?
C9B C8B C11B 120.7(6) . . ?
C5A C10A H10A 119.8 . . ?
C9A C10A C5A 120.3(5) . . ?
C9A C10A H10A 119.8 . . ?
C8B C9B H9BA 119.3 . . ?
C10B C9B C8B 121.3(5) . . ?
C10B C9B H9BA 119.3 . . ?
C8A C11A H11A 109.5 . . ?
C8A C11A H11B 109.5 . . ?
C8A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C8B C11B H11D 109.5 . . ?
C8B C11B H11E 109.5 . . ?
C8B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C5B C10B H10B 120.1 . . ?
C9B C10B C5B 119.8(5) . . ?
C9B C10B H10B 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
