# 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_AKIII051_a
_database_code_depnum_ccdc_archive 'CCDC 2220978'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2022-11-21 deposited with the CCDC.	2023-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C264 H280 N24 O48'
_chemical_formula_weight         4557.10

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'
O O 0.0106 0.0060 '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                   28.490(8)
_cell_length_b                   7.868(2)
_cell_length_c                   27.678(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.235(7)
_cell_angle_gamma                90
_cell_volume                     6204(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4006
_cell_measurement_theta_min      2.7780
_cell_measurement_theta_max      18.5717
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             2416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_diffrn_ambient_temperature      296.(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            64251
_diffrn_reflns_av_unetI/netI     0.1318
_diffrn_reflns_av_R_equivalents  0.2005
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         24.313
_diffrn_reflns_theta_full        24.313
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.844
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.844
_reflns_number_total             4266
_reflns_number_gt                2303
_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       'APEX 2'
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  ?
_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)+(0.1878P)²+53.0275P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0083(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4266
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2249
_refine_ls_R_factor_gt           0.1313
_refine_ls_wR_factor_ref         0.3843
_refine_ls_wR_factor_gt          0.3281
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O001 O 0.3846(2) -0.0183(8) 0.5590(2) 0.0536(17) Uani 1 1 d . . . . .
O002 O 0.3794(2) 0.5367(8) 0.4504(2) 0.0535(17) Uani 1 1 d . . . . .
N003 N 0.3946(2) 0.2240(8) 0.6015(2) 0.0409(18) Uani 1 1 d . . . . .
O004 O 0.2637(3) 0.1391(7) 0.7089(2) 0.071(2) Uani 1 1 d . . . . .
N005 N 0.2546(2) -0.0541(8) 0.6488(2) 0.0408(18) Uani 1 1 d . . . . .
N006 N 0.3861(2) 0.2827(8) 0.4154(2) 0.0429(18) Uani 1 1 d . . . . .
O007 O 0.3291(2) 0.7832(8) 0.4989(2) 0.075(2) Uani 1 1 d . . . . .
C008 C 0.5284(3) 0.2242(10) 0.5277(3) 0.043(2) Uani 1 1 d . . . . .
H008 H 0.558097 0.218426 0.541619 0.052 Uiso 1 1 calc R U . . .
C009 C 0.5229(3) 0.2790(10) 0.4810(3) 0.051(2) Uani 1 1 d . . . . .
H009 H 0.548946 0.312408 0.463258 0.061 Uiso 1 1 calc R U . . .
C00A C 0.4903(3) 0.1790(11) 0.5532(3) 0.047(2) Uani 1 1 d . . . . .
H00A H 0.494283 0.148574 0.585430 0.056 Uiso 1 1 calc R U . . .
C00B C 0.4118(3) -0.0294(12) 0.6775(3) 0.052(2) Uani 1 1 d . . . . .
H00B H 0.437064 0.017101 0.661003 0.062 Uiso 1 1 calc R U . . .
C00C C 0.3319(3) 0.5541(10) 0.3416(3) 0.047(2) Uani 1 1 d . . . . .
C00D C 0.3302(3) -0.0477(11) 0.6924(3) 0.048(2) Uani 1 1 d . . . . .
C00E C 0.3750(3) 0.5292(11) 0.3640(3) 0.052(2) Uani 1 1 d . . . . .
C00F C 0.4052(3) 0.1231(13) 0.5660(3) 0.056(3) Uani 1 1 d . . . . .
C00G C 0.3796(3) 0.4515(13) 0.4143(3) 0.053(2) Uani 1 1 d . . . . .
C00H C 0.4148(4) 0.6742(12) 0.3000(4) 0.058(3) Uani 1 1 d . . . . .
H00H H 0.442586 0.712670 0.286292 0.069 Uiso 1 1 calc R U . . .
C00I C 0.4152(4) 0.5865(12) 0.3420(3) 0.059(3) Uani 1 1 d . . . . .
H00I H 0.443930 0.564029 0.356758 0.071 Uiso 1 1 calc R U . . .
C00J C 0.4465(3) 0.1756(11) 0.5342(3) 0.047(2) Uani 1 1 d . . . . .
C00K C 0.4787(4) 0.2848(11) 0.4603(3) 0.052(3) Uani 1 1 d . . . . .
H00K H 0.474679 0.326602 0.429152 0.062 Uiso 1 1 calc R U . . .
C00L C 0.4400(3) 0.2270(11) 0.4867(3) 0.050(2) Uani 1 1 d . . . . .
C00M C 0.3824(4) -0.2223(11) 0.7358(3) 0.058(3) Uani 1 1 d . . . . .
H00M H 0.387767 -0.305399 0.759062 0.070 Uiso 1 1 calc R U . . .
C00N C 0.4198(3) -0.1521(12) 0.7119(3) 0.054(3) Uani 1 1 d . . . . .
H00N H 0.450293 -0.187056 0.718966 0.065 Uiso 1 1 calc R U . . .
C00O C 0.3674(4) 0.0257(11) 0.6670(3) 0.053(2) Uani 1 1 d . . . . .
C00P C 0.3717(5) 0.7053(11) 0.2779(3) 0.069(3) Uani 1 1 d . . . . .
H00P H 0.370272 0.768692 0.249574 0.082 Uiso 1 1 calc R U . . .
C00Q C 0.3375(4) -0.1723(10) 0.7259(3) 0.048(2) Uani 1 1 d . . . . .
H00Q H 0.312300 -0.222270 0.741731 0.058 Uiso 1 1 calc R U . . .
C00R C 0.2805(4) 0.0204(12) 0.6847(3) 0.059(3) Uani 1 1 d . . . . .
C00S C 0.3305(4) 0.6407(12) 0.2985(3) 0.056(3) Uani 1 1 d . . . . .
H00S H 0.301955 0.656682 0.282772 0.067 Uiso 1 1 calc R U . . .
C00T C 0.2646(4) -0.3590(13) 0.6489(3) 0.064(3) Uani 1 1 d . . . . .
C00U C 0.2711(4) -0.2034(11) 0.6226(3) 0.066(3) Uani 1 1 d . . . . .
H00C H 0.254438 -0.211082 0.592089 0.079 Uiso 1 1 calc R U . . .
H00D H 0.304200 -0.189479 0.615628 0.079 Uiso 1 1 calc R U . . .
C00V C 0.4317(4) 0.1045(13) 0.3580(4) 0.071(3) Uani 1 1 d . . . . .
H00E H 0.428006 0.023464 0.332382 0.107 Uiso 1 1 calc R U . . .
H00F H 0.447608 0.051919 0.384766 0.107 Uiso 1 1 calc R U . . .
H00G H 0.449718 0.199485 0.346781 0.107 Uiso 1 1 calc R U . . .
C00W C 0.3553(3) 0.1732(12) 0.6333(4) 0.061(3) Uani 1 1 d . . . . .
H00J H 0.328695 0.141003 0.613388 0.073 Uiso 1 1 calc R U . . .
H00L H 0.346019 0.270294 0.652635 0.073 Uiso 1 1 calc R U . . .
C00X C 0.3831(4) 0.1664(12) 0.3744(4) 0.068(3) Uani 1 1 d . . . . .
H00X H 0.370198 0.232766 0.347481 0.081 Uiso 1 1 calc R U . . .
C00Y C 0.4137(4) 0.3960(11) 0.6094(4) 0.064(3) Uani 1 1 d . . . . .
H00Y H 0.438594 0.411967 0.585470 0.077 Uiso 1 1 calc R U . . .
C00Z C 0.3900(4) 0.2107(13) 0.4649(3) 0.064(3) Uani 1 1 d . . . . .
H00O H 0.381322 0.091557 0.463958 0.076 Uiso 1 1 calc R U . . .
H00R H 0.367988 0.268713 0.485847 0.076 Uiso 1 1 calc R U . . .
O010 O 0.2463(4) 0.9583(11) 0.4863(4) 0.129(3) Uani 1 1 d . . . . .
C011 C 0.4358(4) 0.4221(14) 0.6577(4) 0.079(3) Uani 1 1 d . . . . .
H01A H 0.459784 0.338259 0.662695 0.118 Uiso 1 1 calc R U . . .
H01B H 0.412361 0.411442 0.682305 0.118 Uiso 1 1 calc R U . . .
H01C H 0.449453 0.533562 0.659113 0.118 Uiso 1 1 calc R U . . .
C012 C 0.2613(4) -0.4846(15) 0.6705(4) 0.075(3) Uani 1 1 d . . . . .
H012 H 0.258716 -0.585378 0.687896 0.090 Uiso 1 1 calc R U . . .
C013 C 0.2109(3) 0.0206(12) 0.6345(4) 0.067(3) Uani 1 1 d . . . . .
H01D H 0.207516 0.008625 0.599815 0.080 Uiso 1 1 calc R U . . .
H01E H 0.212066 0.141158 0.641718 0.080 Uiso 1 1 calc R U . . .
C014 C 0.3754(4) 0.5320(14) 0.5982(5) 0.097(4) Uani 1 1 d . . . . .
H01F H 0.388596 0.643521 0.601953 0.146 Uiso 1 1 calc R U . . .
H01G H 0.349702 0.518277 0.620163 0.146 Uiso 1 1 calc R U . . .
H01H H 0.364408 0.517799 0.565646 0.146 Uiso 1 1 calc R U . . .
C015 C 0.3499(5) 0.0205(13) 0.3819(4) 0.090(4) Uani 1 1 d . . . . .
H01I H 0.345187 -0.037976 0.351820 0.135 Uiso 1 1 calc R U . . .
H01J H 0.320391 0.062721 0.393395 0.135 Uiso 1 1 calc R U . . .
H01K H 0.362986 -0.056566 0.405229 0.135 Uiso 1 1 calc R U . . .
O016 O 0.2341(6) 1.2825(17) 0.4448(5) 0.197(6) Uani 1 1 d . . . . .


_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
O001 C00F 1.272(11) . ?
O002 C00G 1.204(10) . ?
N003 C00F 1.300(11) . ?
N003 C00Y 1.475(11) . ?
N003 C00W 1.481(11) . ?
O004 C00R 1.246(11) . ?
N005 C00R 1.370(11) . ?
N005 C013 1.429(11) . ?
N005 C00U 1.459(11) . ?
N006 C00G 1.341(11) . ?
N006 C00X 1.460(12) . ?
N006 C00Z 1.486(11) . ?
C008 C00A 1.344(12) . ?
C008 C009 1.371(12) . ?
C009 C00K 1.382(12) . ?
C00A C00J 1.352(12) . ?
C00B C00O 1.366(13) . ?
C00B C00N 1.375(12) . ?
C00C C00S 1.375(12) . ?
C00C C00E 1.388(12) . ?
C00C C013 1.508(13) 7_556 ?
C00D C00Q 1.364(12) . ?
C00D C00O 1.399(12) . ?
C00D C00R 1.527(13) . ?
C00E C00I 1.373(13) . ?
C00E C00G 1.526(13) . ?
C00F C00J 1.530(13) . ?
C00H C00I 1.352(13) . ?
C00H C00P 1.391(14) . ?
C00J C00L 1.389(12) . ?
C00K C00L 1.399(13) . ?
C00L C00Z 1.550(13) . ?
C00M C00Q 1.366(13) . ?
C00M C00N 1.372(13) . ?
C00O C00W 1.527(12) . ?
C00P C00S 1.402(14) . ?
C00T C012 1.159(13) . ?
C00T C00U 1.436(14) . ?
C00V C00X 1.538(14) . ?
C00X C015 1.501(14) . ?
C00Y C011 1.488(14) . ?
C00Y C014 1.558(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
C00F N003 C00Y 125.8(8) . . ?
C00F N003 C00W 117.5(8) . . ?
C00Y N003 C00W 116.1(7) . . ?
C00R N005 C013 119.5(7) . . ?
C00R N005 C00U 122.0(8) . . ?
C013 N005 C00U 118.5(7) . . ?
C00G N006 C00X 126.5(7) . . ?
C00G N006 C00Z 114.1(7) . . ?
C00X N006 C00Z 118.8(7) . . ?
C00A C008 C009 119.3(8) . . ?
C008 C009 C00K 120.1(9) . . ?
C008 C00A C00J 123.2(8) . . ?
C00O C00B C00N 121.5(9) . . ?
C00S C00C C00E 118.6(9) . . ?
C00S C00C C013 123.6(9) . 7_556 ?
C00E C00C C013 117.8(8) . 7_556 ?
C00Q C00D C00O 121.7(8) . . ?
C00Q C00D C00R 119.0(8) . . ?
C00O C00D C00R 119.2(8) . . ?
C00I C00E C00C 119.6(8) . . ?
C00I C00E C00G 117.8(8) . . ?
C00C C00E C00G 122.4(8) . . ?
O001 C00F N003 122.8(9) . . ?
O001 C00F C00J 120.2(9) . . ?
N003 C00F C00J 116.8(8) . . ?
O002 C00G N006 122.3(9) . . ?
O002 C00G C00E 122.3(9) . . ?
N006 C00G C00E 115.4(8) . . ?
C00I C00H C00P 118.2(10) . . ?
C00H C00I C00E 122.9(9) . . ?
C00A C00J C00L 118.7(9) . . ?
C00A C00J C00F 119.6(8) . . ?
C00L C00J C00F 121.6(8) . . ?
C009 C00K C00L 119.4(8) . . ?
C00J C00L C00K 119.2(8) . . ?
C00J C00L C00Z 117.5(8) . . ?
C00K C00L C00Z 123.3(8) . . ?
C00Q C00M C00N 121.1(9) . . ?
C00M C00N C00B 119.2(9) . . ?
C00B C00O C00D 117.7(8) . . ?
C00B C00O C00W 125.2(9) . . ?
C00D C00O C00W 116.9(8) . . ?
C00H C00P C00S 119.7(9) . . ?
C00D C00Q C00M 118.9(9) . . ?
O004 C00R N005 120.2(9) . . ?
O004 C00R C00D 123.1(9) . . ?
N005 C00R C00D 116.7(8) . . ?
C00C C00S C00P 120.8(9) . . ?
C012 C00T C00U 177.2(13) . . ?
C00T C00U N005 113.1(8) . . ?
N003 C00W C00O 113.6(8) . . ?
N006 C00X C015 114.1(8) . . ?
N006 C00X C00V 112.1(8) . . ?
C015 C00X C00V 111.4(9) . . ?
N003 C00Y C011 114.4(8) . . ?
N003 C00Y C014 110.0(9) . . ?
C011 C00Y C014 112.1(9) . . ?
N006 C00Z C00L 113.0(8) . . ?
N005 C013 C00C 115.0(8) . 7_556 ?

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.147



