# Electronic Supplementary Material (ESI) 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 
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data_cu_azac_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2336236'
loop_
_audit_author_name
_audit_author_address
'Jianwen Guo'
;Shanghai University
China
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_audit_creation_date             2024-01-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H50'
_chemical_formula_sum            'C46 H50'
_chemical_formula_weight         602.86
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4401(2)
_cell_length_b                   9.1230(3)
_cell_length_c                   17.9486(6)
_cell_angle_alpha                101.504(3)
_cell_angle_beta                 95.881(2)
_cell_angle_gamma                94.474(2)
_cell_volume                     863.86(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2430
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.01
_cell_measurement_theta_min      4.97
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.8701.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8555
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.185
_diffrn_reflns_theta_min         4.972
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2423
_reflns_number_total             3101
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.051
_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)+(0.0750P)²+0.1384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C22(H22)
1.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.4632(5) 0.8115(5) 0.60528(16) 0.1146(14) Uani 1 1 d . . . . .
H1A H 1.612347 0.791639 0.580139 0.172 Uiso 1 1 calc R U . . .
H1B H 1.469306 0.768201 0.651137 0.172 Uiso 1 1 calc R U . . .
H1C H 1.455559 0.920253 0.619931 0.172 Uiso 1 1 calc R U . . .
C2 C 1.2398(6) 0.7424(4) 0.55179(15) 0.0916(10) Uani 1 1 d . . . . .
H2A H 1.092178 0.757175 0.579393 0.110 Uiso 1 1 calc R U . . .
H2B H 1.251115 0.632746 0.537590 0.110 Uiso 1 1 calc R U . . .
C3 C 1.1978(4) 0.8008(3) 0.47933(12) 0.0616(6) Uani 1 1 d . . . . .
H3A H 1.345380 0.786883 0.451643 0.074 Uiso 1 1 calc R U . . .
H3B H 1.183420 0.910148 0.493190 0.074 Uiso 1 1 calc R U . . .
C4 C 0.9698(4) 0.7265(3) 0.42580(12) 0.0571(6) Uani 1 1 d . . . . .
H4A H 0.982029 0.616764 0.413310 0.069 Uiso 1 1 calc R U . . .
H4B H 0.821993 0.742959 0.453117 0.069 Uiso 1 1 calc R U . . .
C5 C 0.9297(4) 0.7809(2) 0.35198(10) 0.0419(4) Uani 1 1 d . . . . .
H5A H 1.078319 0.766355 0.324833 0.050 Uiso 1 1 calc R U . . .
H5B H 0.912596 0.890111 0.364101 0.050 Uiso 1 1 calc R U . . .
C6 C 0.7015(3) 0.7010(2) 0.29875(9) 0.0372(4) Uani 1 1 d . . . . .
H6A H 0.707583 0.591076 0.292156 0.045 Uiso 1 1 calc R U . . .
H6B H 0.550916 0.726852 0.323102 0.045 Uiso 1 1 calc R U . . .
C7 C 0.6802(3) 0.74142(17) 0.22039(9) 0.0321(4) Uani 1 1 d . . . . .
H7A H 0.836860 0.723560 0.197991 0.039 Uiso 1 1 calc R U . . .
H7B H 0.660731 0.850063 0.226827 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4627(3) 0.65259(17) 0.16389(9) 0.0290(4) Uani 1 1 d . . . . .
H8A H 0.305902 0.670375 0.186225 0.035 Uiso 1 1 calc R U . . .
H8B H 0.454399 0.691477 0.116089 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4818(3) 0.48597(17) 0.14440(9) 0.0272(4) Uani 1 1 d . . . . .
C10 C 0.3472(3) 0.37915(17) 0.17412(9) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.1670(3) 0.40758(19) 0.22448(9) 0.0336(4) Uani 1 1 d . . . . .
H11 H 0.138259 0.510129 0.239324 0.040 Uiso 1 1 calc R U . . .
C12 C 0.0253(3) 0.3080(2) 0.25560(10) 0.0386(4) Uani 1 1 d . . . . .
H12 H -0.088824 0.351990 0.287921 0.046 Uiso 1 1 calc R U . . .
C13 C 0.0253(3) 0.1518(2) 0.24648(10) 0.0398(4) Uani 1 1 d . . . . .
H13 H -0.089323 0.105030 0.273237 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1677(3) 0.0566(2) 0.20426(10) 0.0397(4) Uani 1 1 d . . . . .
H14 H 0.141512 -0.046339 0.206864 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3467(3) 0.09182(18) 0.15781(9) 0.0335(4) Uani 1 1 d . . . . .
H15 H 0.425680 0.009302 0.133234 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4234(3) 0.22868(17) 0.14300(9) 0.0290(4) Uani 1 1 d . . . . .
C17 C 0.6039(3) 0.25268(17) 0.09323(9) 0.0277(4) Uani 1 1 d . . . . .
C18 C 0.6411(3) 0.40821(17) 0.09371(8) 0.0263(3) Uani 1 1 d . . . . .
C19 C 0.7352(3) 0.14605(17) 0.04931(9) 0.0313(4) Uani 1 1 d . . . . .
H19 H 0.704718 0.042266 0.049696 0.038 Uiso 1 1 calc R U . . .
C20 C 0.9051(3) 0.19285(17) 0.00663(9) 0.0315(4) Uani 1 1 d . . . . .
H20 H 0.994563 0.120943 -0.022285 0.038 Uiso 1 1 calc R U . . .
C21 C 0.9526(3) 0.34826(17) 0.00415(8) 0.0270(4) Uani 1 1 d . . . . .
C22 C 1.1280(3) 0.39222(17) -0.04066(8) 0.0274(3) Uani 1 1 d . . . . .
H22 H 1.215681 0.317245 -0.068090 0.033 Uiso 1 1 calc R U . . .
C23 C 1.1809(3) 0.54060(17) -0.04718(8) 0.0265(3) 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.482(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.504(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.512(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.507(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.524(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.519(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.537(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.505(2) . ?
C9 C10 1.395(2) . ?
C9 C18 1.443(2) . ?
C10 C11 1.405(2) . ?
C10 C16 1.483(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.402(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.404(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(2) . ?
C16 C17 1.426(2) . ?
C17 C18 1.416(2) . ?
C17 C19 1.413(2) . ?
C18 C23 1.450(2) 2_765 ?
C19 H19 0.9500 . ?
C19 C20 1.355(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.432(2) . ?
C21 C22 1.395(2) . ?
C21 C23 1.438(2) 2_765 ?
C22 H22 0.9500 . ?
C22 C23 1.392(2) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C1 C2 C3 116.2(3) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C2 C3 C4 114.7(2) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 C3 115.17(19) . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C4 C5 C6 113.67(17) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.51(15) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.17(13) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.84(12) . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C10 C9 C8 124.93(15) . . ?
C10 C9 C18 107.94(13) . . ?
C18 C9 C8 127.13(14) . . ?
C9 C10 C11 126.18(15) . . ?
C9 C10 C16 108.68(14) . . ?
C11 C10 C16 125.14(15) . . ?
C10 C11 H11 115.3 . . ?
C12 C11 C10 129.42(16) . . ?
C12 C11 H11 115.3 . . ?
C11 C12 H12 115.2 . . ?
C11 C12 C13 129.52(17) . . ?
C13 C12 H12 115.2 . . ?
C12 C13 H13 115.4 . . ?
C14 C13 C12 129.13(17) . . ?
C14 C13 H13 115.4 . . ?
C13 C14 H14 115.8 . . ?
C13 C14 C15 128.43(16) . . ?
C15 C14 H14 115.8 . . ?
C14 C15 H15 115.5 . . ?
C16 C15 C14 128.99(17) . . ?
C16 C15 H15 115.5 . . ?
C15 C16 C10 129.30(15) . . ?
C15 C16 C17 124.84(15) . . ?
C17 C16 C10 105.85(13) . . ?
C18 C17 C16 109.07(14) . . ?
C19 C17 C16 128.74(15) . . ?
C19 C17 C18 122.19(15) . . ?
C9 C18 C23 132.75(14) . 2_765 ?
C17 C18 C9 108.46(14) . . ?
C17 C18 C23 118.79(14) . 2_765 ?
C17 C19 H19 120.2 . . ?
C20 C19 C17 119.55(15) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.45(15) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C23 120.41(15) . 2_765 ?
C22 C21 C20 119.86(14) . . ?
C22 C21 C23 119.73(14) . 2_765 ?
C21 C22 H22 118.4 . . ?
C23 C22 C21 123.21(15) . . ?
C23 C22 H22 118.4 . . ?
C21 C23 C18 117.59(14) 2_765 2_765 ?
C22 C23 C18 125.35(14) . 2_765 ?
C22 C23 C21 117.06(15) . 2_765 ?

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
C1 C2 C3 C4 179.3(3) . . . . ?
C2 C3 C4 C5 -178.3(2) . . . . ?
C3 C4 C5 C6 178.71(18) . . . . ?
C4 C5 C6 C7 -172.48(17) . . . . ?
C5 C6 C7 C8 175.42(14) . . . . ?
C6 C7 C8 C9 -63.04(19) . . . . ?
C7 C8 C9 C10 102.96(17) . . . . ?
C7 C8 C9 C18 -76.01(19) . . . . ?
C8 C9 C10 C11 2.4(2) . . . . ?
C8 C9 C10 C16 -178.27(13) . . . . ?
C8 C9 C18 C17 178.67(13) . . . . ?
C8 C9 C18 C23 -1.1(3) . . . 2_765 ?
C9 C10 C11 C12 179.34(16) . . . . ?
C9 C10 C16 C15 177.96(15) . . . . ?
C9 C10 C16 C17 -0.96(16) . . . . ?
C10 C9 C18 C17 -0.45(16) . . . . ?
C10 C9 C18 C23 179.74(15) . . . 2_765 ?
C10 C11 C12 C13 1.2(3) . . . . ?
C10 C16 C17 C18 0.67(16) . . . . ?
C10 C16 C17 C19 179.93(14) . . . . ?
C11 C10 C16 C15 -2.7(2) . . . . ?
C11 C10 C16 C17 178.38(14) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C10 2.8(3) . . . . ?
C14 C15 C16 C17 -178.48(16) . . . . ?
C15 C16 C17 C18 -178.30(14) . . . . ?
C15 C16 C17 C19 1.0(3) . . . . ?
C16 C10 C11 C12 0.1(3) . . . . ?
C16 C17 C18 C9 -0.17(17) . . . . ?
C16 C17 C18 C23 179.68(12) . . . 2_765 ?
C16 C17 C19 C20 -178.42(15) . . . . ?
C17 C19 C20 C21 -0.8(2) . . . . ?
C18 C9 C10 C11 -178.47(14) . . . . ?
C18 C9 C10 C16 0.86(16) . . . . ?
C18 C17 C19 C20 0.8(2) . . . . ?
C19 C17 C18 C9 -179.48(13) . . . . ?
C19 C17 C18 C23 0.4(2) . . . 2_765 ?
C19 C20 C21 C22 -179.74(14) . . . . ?
C19 C20 C21 C23 -0.2(2) . . . 2_765 ?
C20 C21 C22 C23 178.71(13) . . . . ?
C21 C22 C23 C18 -179.14(13) . . . 2_765 ?
C21 C22 C23 C21 0.8(2) . . . 2_765 ?
C23 C21 C22 C23 -0.8(2) 2_765 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
