# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AJ1609_tw
_database_code_depnum_ccdc_archive 'CCDC 2056322'
loop_
_audit_author_name
_audit_author_address
'Anukul Jana'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H48 N2'
_chemical_formula_sum            'C24 H48 N2'
_chemical_formula_weight         364.64

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   18.4911(16)
_cell_length_b                   8.0630(7)
_cell_length_c                   15.8001(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.727(7)
_cell_angle_gamma                90
_cell_volume                     2339.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2926
_cell_measurement_theta_min      3.0790
_cell_measurement_theta_max      21.0430

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.035
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2376
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2376
_reflns_number_gt                1530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+3.0596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.1996
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
N1 N 0.41357(12) 0.7515(3) 0.66460(14) 0.0399(6) Uani 1 1 d . . . . .
C1 C 0.45676(14) 0.7583(3) 0.75137(15) 0.0373(6) Uani 1 1 d . . . . .
H1 H 0.446707 0.652164 0.777888 0.045 Uiso 1 1 calc R U . . .
C2 C 0.41694(16) 0.8905(4) 0.80209(18) 0.0470(7) Uani 1 1 d . . . . .
C3 C 0.37481(17) 0.9911(4) 0.7323(2) 0.0571(8) Uani 1 1 d . . . . .
H3A H 0.404773 1.080895 0.715062 0.069 Uiso 1 1 calc R U . . .
H3B H 0.331815 1.038589 0.752642 0.069 Uiso 1 1 calc R U . . .
C4 C 0.35269(16) 0.8754(4) 0.65671(18) 0.0486(8) Uani 1 1 d . . . . .
C5 C 0.27443(17) 0.8132(5) 0.6637(2) 0.0674(10) Uani 1 1 d . . . . .
H5A H 0.259906 0.737546 0.617972 0.101 Uiso 1 1 calc R U . . .
H5B H 0.241642 0.905891 0.660341 0.101 Uiso 1 1 calc R U . . .
H5C H 0.273213 0.757541 0.717270 0.101 Uiso 1 1 calc R U . . .
C6 C 0.3489(2) 0.9777(5) 0.5739(2) 0.0692(10) Uani 1 1 d . . . . .
H6A H 0.397041 1.012797 0.564884 0.104 Uiso 1 1 calc R U . . .
H6B H 0.318673 1.073259 0.578555 0.104 Uiso 1 1 calc R U . . .
H6C H 0.328728 0.910778 0.526709 0.104 Uiso 1 1 calc R U . . .
C7 C 0.46313(19) 1.0048(5) 0.8624(2) 0.0694(10) Uani 1 1 d . . . . .
H7A H 0.491177 0.940121 0.905477 0.104 Uiso 1 1 calc R U . . .
H7B H 0.432120 1.079503 0.888792 0.104 Uiso 1 1 calc R U . . .
H7C H 0.495367 1.067207 0.831120 0.104 Uiso 1 1 calc R U . . .
C8 C 0.36643(19) 0.7983(5) 0.8570(2) 0.0672(10) Uani 1 1 d . . . . .
H8A H 0.338774 0.716590 0.822886 0.101 Uiso 1 1 calc R U . . .
H8B H 0.333850 0.876052 0.878688 0.101 Uiso 1 1 calc R U . . .
H8C H 0.395149 0.744719 0.903725 0.101 Uiso 1 1 calc R U . . .
C9 C 0.39954(17) 0.5830(4) 0.62631(19) 0.0506(8) Uani 1 1 d . . . . .
C10 C 0.47087(18) 0.4896(4) 0.6199(2) 0.0653(10) Uani 1 1 d . . . . .
H10A H 0.503771 0.559731 0.593589 0.098 Uiso 1 1 calc R U . . .
H10B H 0.461036 0.391447 0.586165 0.098 Uiso 1 1 calc R U . . .
H10C H 0.492502 0.459262 0.675973 0.098 Uiso 1 1 calc R U . . .
C11 C 0.3530(2) 0.4694(4) 0.6768(3) 0.0749(11) Uani 1 1 d . . . . .
H11A H 0.373942 0.465130 0.735330 0.112 Uiso 1 1 calc R U . . .
H11B H 0.351701 0.359839 0.652977 0.112 Uiso 1 1 calc R U . . .
H11C H 0.304377 0.512654 0.673649 0.112 Uiso 1 1 calc R U . . .
C12 C 0.3643(2) 0.5997(5) 0.5338(2) 0.0735(11) Uani 1 1 d . . . . .
H12A H 0.317991 0.653976 0.532900 0.110 Uiso 1 1 calc R U . . .
H12B H 0.357421 0.491484 0.508840 0.110 Uiso 1 1 calc R U . . .
H12C H 0.395383 0.664011 0.501949 0.110 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 C9 1.498(4) . ?
N1 C4 1.499(4) . ?
N1 C1 1.505(3) . ?
C1 C2 1.568(4) . ?
C1 C1 1.605(5) 2_656 ?
C1 H1 0.9800 . ?
C2 C3 1.509(4) . ?
C2 C7 1.515(4) . ?
C2 C8 1.539(4) . ?
C3 C4 1.533(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.541(4) . ?
C4 C5 1.548(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.533(4) . ?
C9 C12 1.534(4) . ?
C9 C11 1.542(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C9 N1 C4 118.6(2) . . ?
C9 N1 C1 116.7(2) . . ?
C4 N1 C1 111.4(2) . . ?
N1 C1 C2 105.0(2) . . ?
N1 C1 C1 113.6(2) . 2_656 ?
C2 C1 C1 122.9(2) . 2_656 ?
N1 C1 H1 104.5 . . ?
C2 C1 H1 104.5 . . ?
C1 C1 H1 104.5 2_656 . ?
C3 C2 C7 109.7(3) . . ?
C3 C2 C8 112.1(3) . . ?
C7 C2 C8 105.9(3) . . ?
C3 C2 C1 103.0(2) . . ?
C7 C2 C1 118.1(2) . . ?
C8 C2 C1 108.2(3) . . ?
C2 C3 C4 108.0(3) . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N1 C4 C3 102.2(2) . . ?
N1 C4 C6 112.7(2) . . ?
C3 C4 C6 108.5(3) . . ?
N1 C4 C5 118.5(3) . . ?
C3 C4 C5 107.9(3) . . ?
C6 C4 C5 106.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 111.3(2) . . ?
N1 C9 C12 109.9(3) . . ?
C10 C9 C12 104.7(3) . . ?
N1 C9 C11 114.2(3) . . ?
C10 C9 C11 106.2(3) . . ?
C12 C9 C11 110.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_AJ1598-1
_database_code_depnum_ccdc_archive 'CCDC 2056323'
loop_
_audit_author_name
_audit_author_address
'Anukul Jana'
;Tata Institute of Fundamental Research Hyderabad
India
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H64 N2'
_chemical_formula_sum            'C40 H64 N2'
_chemical_formula_weight         572.93

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   19.980(2)
_cell_length_b                   9.5392(8)
_cell_length_c                   20.618(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.474(15)
_cell_angle_gamma                90
_cell_volume                     3547.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4632
_cell_measurement_theta_min      2.9070
_cell_measurement_theta_max      23.1240

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25298
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_av_R_equivalents  0.1445
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3124
_reflns_number_gt                2139
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 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)+(0.0793P)²+1.1511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0084(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3124
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
N1 N 0.57763(8) 0.51794(15) 0.34497(7) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.50061(9) 0.49166(17) 0.28852(8) 0.0343(4) Uani 1 1 d . . . . .
H1 H 0.471830 0.574161 0.289495 0.041 Uiso 1 1 calc R U . . .
C2 C 0.47091(10) 0.36786(19) 0.31980(10) 0.0460(5) Uani 1 1 d . . . . .
C3 C 0.54150(11) 0.3063(2) 0.37887(11) 0.0557(6) Uani 1 1 d . . . . .
H3A H 0.530758 0.266371 0.416630 0.067 Uiso 1 1 calc R U . . .
H3B H 0.560914 0.232709 0.359294 0.067 Uiso 1 1 calc R U . . .
C4 C 0.59803(11) 0.4237(2) 0.40899(10) 0.0520(5) Uani 1 1 d . . . . .
C5 C 0.59625(14) 0.4961(3) 0.47501(11) 0.0697(7) Uani 1 1 d . . . . .
H5A H 0.627984 0.576867 0.487510 0.105 Uiso 1 1 calc R U . . .
H5B H 0.613213 0.431839 0.514700 0.105 Uiso 1 1 calc R U . . .
H5C H 0.546441 0.524670 0.463972 0.105 Uiso 1 1 calc R U . . .
C6 C 0.67614(13) 0.3636(3) 0.43475(13) 0.0778(7) Uani 1 1 d . . . . .
H6A H 0.681498 0.321324 0.394986 0.117 Uiso 1 1 calc R U . . .
H6B H 0.684176 0.294158 0.471054 0.117 Uiso 1 1 calc R U . . .
H6C H 0.711839 0.437536 0.454385 0.117 Uiso 1 1 calc R U . . .
C7 C 0.42056(12) 0.4245(2) 0.35335(12) 0.0612(6) Uani 1 1 d . . . . .
H7A H 0.444855 0.501088 0.384915 0.092 Uiso 1 1 calc R U . . .
H7B H 0.410887 0.351164 0.380072 0.092 Uiso 1 1 calc R U . . .
H7C H 0.374606 0.456398 0.315927 0.092 Uiso 1 1 calc R U . . .
C8 C 0.42392(12) 0.2550(2) 0.26717(13) 0.0623(6) Uani 1 1 d . . . . .
H8A H 0.382917 0.298291 0.228173 0.093 Uiso 1 1 calc R U . . .
H8B H 0.405598 0.190736 0.291582 0.093 Uiso 1 1 calc R U . . .
H8C H 0.453772 0.205118 0.248725 0.093 Uiso 1 1 calc R U . . .
C9 C 0.61086(10) 0.65681(19) 0.35724(9) 0.0434(5) Uani 1 1 d . . . . .
C10 C 0.67976(11) 0.6769(2) 0.35394(11) 0.0593(6) Uani 1 1 d . . . . .
C11 C 0.71443(15) 0.8065(3) 0.37136(15) 0.0839(8) Uani 1 1 d . . . . .
H11 H 0.760614 0.817134 0.371167 0.101 Uiso 1 1 calc R U . . .
C12 C 0.68339(18) 0.9186(3) 0.38870(16) 0.0931(9) Uani 1 1 d . . . . .
H12 H 0.707619 1.004599 0.399745 0.112 Uiso 1 1 calc R U . . .
C13 C 0.61640(16) 0.9024(2) 0.38959(13) 0.0748(7) Uani 1 1 d . . . . .
H13 H 0.594531 0.979862 0.400088 0.090 Uiso 1 1 calc R U . . .
C14 C 0.57873(12) 0.7743(2) 0.37538(10) 0.0506(5) Uani 1 1 d . . . . .
C15 C 0.50484(12) 0.7750(2) 0.37907(10) 0.0540(5) Uani 1 1 d . . . . .
H15 H 0.486915 0.678088 0.373641 0.065 Uiso 1 1 calc R U . . .
C16 C 0.50982(17) 0.8312(3) 0.45112(14) 0.0847(8) Uani 1 1 d . . . . .
H16A H 0.547111 0.780119 0.490005 0.127 Uiso 1 1 calc R U . . .
H16B H 0.462789 0.819660 0.452653 0.127 Uiso 1 1 calc R U . . .
H16C H 0.522656 0.928852 0.455558 0.127 Uiso 1 1 calc R U . . .
C17 C 0.44807(15) 0.8608(3) 0.31784(14) 0.0776(7) Uani 1 1 d . . . . .
H17A H 0.464738 0.956139 0.321626 0.116 Uiso 1 1 calc R U . . .
H17B H 0.401317 0.858063 0.320567 0.116 Uiso 1 1 calc R U . . .
H17C H 0.442370 0.822337 0.272730 0.116 Uiso 1 1 calc R U . . .
C18 C 0.71910(12) 0.5682(3) 0.32923(14) 0.0727(7) Uani 1 1 d . . . . .
H18 H 0.688910 0.482781 0.315801 0.087 Uiso 1 1 calc R U . . .
C19 C 0.72833(16) 0.6215(4) 0.26318(16) 0.1003(10) Uani 1 1 d . . . . .
H19A H 0.680631 0.645239 0.225786 0.150 Uiso 1 1 calc R U . . .
H19B H 0.750631 0.549600 0.246409 0.150 Uiso 1 1 calc R U . . .
H19C H 0.759494 0.703131 0.276090 0.150 Uiso 1 1 calc R U . . .
C20 C 0.79714(14) 0.5306(4) 0.38782(19) 0.1175(12) Uani 1 1 d . . . . .
H20A H 0.831295 0.604143 0.391220 0.176 Uiso 1 1 calc R U . . .
H20B H 0.813457 0.444343 0.375332 0.176 Uiso 1 1 calc R U . . .
H20C H 0.795052 0.519992 0.433212 0.176 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 C9 1.454(2) . ?
N1 C1 1.498(2) . ?
N1 C4 1.501(2) . ?
C1 C1 1.578(3) 2_655 ?
C1 C2 1.579(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.530(3) . ?
C2 C8 1.530(3) . ?
C2 C7 1.543(3) . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.528(3) . ?
C4 C5 1.540(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.419(3) . ?
C9 C10 1.420(3) . ?
C10 C11 1.387(3) . ?
C10 C18 1.516(3) . ?
C11 C12 1.358(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.355(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.511(3) . ?
C15 C17 1.523(3) . ?
C15 C16 1.542(3) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.538(4) . ?
C18 C20 1.549(4) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C9 N1 C1 121.80(13) . . ?
C9 N1 C4 117.48(14) . . ?
C1 N1 C4 112.49(13) . . ?
N1 C1 C1 110.37(15) . 2_655 ?
N1 C1 C2 104.41(13) . . ?
C1 C1 C2 124.43(11) 2_655 . ?
N1 C1 H1 105.4 . . ?
C1 C1 H1 105.4 2_655 . ?
C2 C1 H1 105.4 . . ?
C3 C2 C8 111.64(17) . . ?
C3 C2 C7 109.46(16) . . ?
C8 C2 C7 104.17(17) . . ?
C3 C2 C1 103.45(14) . . ?
C8 C2 C1 117.42(16) . . ?
C7 C2 C1 110.70(15) . . ?
C4 C3 C2 108.11(15) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N1 C4 C3 102.06(14) . . ?
N1 C4 C6 112.39(16) . . ?
C3 C4 C6 109.49(18) . . ?
N1 C4 C5 114.09(16) . . ?
C3 C4 C5 113.30(17) . . ?
C6 C4 C5 105.64(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 117.63(17) . . ?
C14 C9 N1 122.73(16) . . ?
C10 C9 N1 119.60(16) . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 C18 115.1(2) . . ?
C9 C10 C18 125.26(18) . . ?
C12 C11 C10 122.4(2) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 122.8(2) . . ?
C12 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C9 118.8(2) . . ?
C13 C14 C15 115.79(19) . . ?
C9 C14 C15 125.40(17) . . ?
C14 C15 C17 110.86(18) . . ?
C14 C15 C16 112.99(18) . . ?
C17 C15 C16 109.15(18) . . ?
C14 C15 H15 107.9 . . ?
C17 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 C19 110.4(2) . . ?
C10 C18 C20 112.9(2) . . ?
C19 C18 C20 107.7(2) . . ?
C10 C18 H18 108.6 . . ?
C19 C18 H18 108.6 . . ?
C20 C18 H18 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.053



