# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2286p1_a
_database_code_depnum_ccdc_archive 'CCDC 2313182'
_audit_update_record             
;
2023-12-09 deposited with the CCDC.	2024-04-03 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         'C61 H40 N8 O'
_chemical_formula_sum            'C61 H40 N8 O'
_chemical_formula_weight         901.01

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.5461(5)
_cell_length_b                   11.3648(6)
_cell_length_c                   13.2742(8)
_cell_angle_alpha                66.284(2)
_cell_angle_beta                 72.713(2)
_cell_angle_gamma                85.367(2)
_cell_volume                     1257.70(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.89

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             470
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19602
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.044
_diffrn_reflns_theta_max         26.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4933
_reflns_number_gt                3804
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.7754P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4933
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1954
_refine_ls_wR_factor_gt          0.1827
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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
N2 N 0.70769(19) 0.37032(17) 0.60250(14) 0.0439(4) Uani 1 1 d . . . . .
N1 N 0.77571(19) 0.51926(18) 0.42423(15) 0.0463(4) Uani 1 1 d . . . . .
C8 C 0.7665(2) 0.4744(2) 0.60782(18) 0.0434(5) Uani 1 1 d . . . . .
C1 C 0.8075(2) 0.5653(2) 0.49667(18) 0.0440(5) Uani 1 1 d . . . . .
C16 C 0.5286(2) 0.2529(2) 0.79255(17) 0.0445(5) Uani 1 1 d . . . . .
C23 C 0.7154(2) 0.4027(2) 0.48969(17) 0.0441(5) Uani 1 1 d . . . . .
C24 C 0.6636(2) 0.3207(2) 0.44446(18) 0.0465(5) Uani 1 1 d . . . . .
C17 C 0.4141(3) 0.3292(2) 0.76583(18) 0.0512(6) Uani 1 1 d . . . . .
H17 H 0.421467 0.380991 0.689397 0.061 Uiso 1 1 calc R U . . .
C9 C 0.7643(2) 0.4758(2) 0.71956(18) 0.0462(5) Uani 1 1 d . . . . .
C2 C 0.8737(2) 0.6961(2) 0.45208(19) 0.0472(5) Uani 1 1 d . . . . .
C15 C 0.6632(3) 0.2462(2) 0.70036(18) 0.0481(5) Uani 1 1 d . . . . .
H15A H 0.743762 0.216428 0.733625 0.058 Uiso 1 1 calc R U . . .
H15B H 0.643606 0.183796 0.672936 0.058 Uiso 1 1 calc R U . . .
C19 C 0.2785(3) 0.2544(3) 0.9647(2) 0.0591(6) Uani 1 1 d . . . . .
C25 C 0.7491(3) 0.3163(2) 0.34028(19) 0.0542(6) Uani 1 1 d . . . . .
H25 H 0.838795 0.362402 0.302590 0.065 Uiso 1 1 calc R U . . .
C29 C 0.5298(3) 0.2511(2) 0.4987(2) 0.0525(6) Uani 1 1 d . . . . .
H29 H 0.471410 0.253009 0.567954 0.063 Uiso 1 1 calc R U . . .
C27 C 0.5688(3) 0.1758(2) 0.3484(2) 0.0540(6) Uani 1 1 d . . . . .
C18 C 0.2894(3) 0.3299(2) 0.8503(2) 0.0570(6) Uani 1 1 d . . . . .
H18 H 0.212431 0.380814 0.830914 0.068 Uiso 1 1 calc R U . . .
C26 C 0.7023(3) 0.2446(3) 0.2927(2) 0.0595(6) Uani 1 1 d . . . . .
H26 H 0.760251 0.242544 0.223489 0.071 Uiso 1 1 calc R U . . .
C21 C 0.5175(3) 0.1791(2) 0.9074(2) 0.0605(6) Uani 1 1 d . . . . .
H21 H 0.594790 0.128583 0.926644 0.073 Uiso 1 1 calc R U . . .
C28 C 0.4821(3) 0.1794(2) 0.4518(2) 0.0566(6) Uani 1 1 d . . . . .
H28 H 0.392297 0.133481 0.489032 0.068 Uiso 1 1 calc R U . . .
C7 C 0.8592(3) 0.7895(2) 0.3492(2) 0.0593(6) Uani 1 1 d . . . . .
H7 H 0.808720 0.768923 0.307918 0.071 Uiso 1 1 calc R U . . .
C3 C 0.9521(3) 0.7301(2) 0.5104(2) 0.0589(6) Uani 1 1 d . . . . .
H3 H 0.963874 0.669325 0.579143 0.071 Uiso 1 1 calc R U . . .
C14 C 0.8581(3) 0.4048(3) 0.7807(2) 0.0652(7) Uani 1 1 d . . . . .
H14 H 0.928774 0.357611 0.749843 0.078 Uiso 1 1 calc R U . . .
C20 C 0.3939(3) 0.1796(3) 0.9934(2) 0.0693(8) Uani 1 1 d . . . . .
H20 H 0.387933 0.130096 1.070020 0.083 Uiso 1 1 calc R U . . .
C10 C 0.6630(3) 0.5478(3) 0.7659(2) 0.0661(7) Uani 1 1 d . . . . .
H10 H 0.599473 0.596895 0.725495 0.079 Uiso 1 1 calc R U . . .
C30 C 0.5182(4) 0.1028(3) 0.2980(2) 0.0709(8) Uani 1 1 d . . . . .
N3 N 0.4773(4) 0.0448(3) 0.2581(3) 0.1067(11) Uani 1 1 d . . . . .
N4 N 0.0410(3) 0.2509(4) 1.1220(3) 0.1109(11) Uani 1 1 d . . . . .
C22 C 0.1465(3) 0.2526(3) 1.0534(2) 0.0779(8) Uani 1 1 d . . . . .
C6 C 0.9191(4) 0.9129(3) 0.3076(3) 0.0751(8) Uani 1 1 d . . . . .
H6 H 0.906911 0.974568 0.239263 0.090 Uiso 1 1 calc R U . . .
C4 C 1.0126(3) 0.8537(3) 0.4670(3) 0.0736(8) Uani 1 1 d . . . . .
H4 H 1.064955 0.875089 0.506574 0.088 Uiso 1 1 calc R U . . .
C5 C 0.9955(4) 0.9452(3) 0.3652(3) 0.0791(9) Uani 1 1 d . . . . .
H5 H 1.035909 1.028202 0.336212 0.095 Uiso 1 1 calc R U . . .
C11 C 0.6546(4) 0.5477(3) 0.8721(3) 0.0892(10) Uani 1 1 d . . . . .
H11 H 0.586705 0.597352 0.901961 0.107 Uiso 1 1 calc R U . . .
C13 C 0.8482(4) 0.4027(4) 0.8879(3) 0.0833(9) Uani 1 1 d . . . . .
H13 H 0.910391 0.352878 0.929309 0.100 Uiso 1 1 calc R U . . .
C12 C 0.7459(4) 0.4749(4) 0.9325(3) 0.0896(10) Uani 1 1 d . . . . .
H12 H 0.739049 0.473837 1.004224 0.108 Uiso 1 1 calc R U . . .
C31 C 0.0656(8) 0.9447(7) 1.0167(5) 0.0726(16) Uani 0.5 1 d . . P . .
O2 O 0.2000(10) 0.9629(6) 0.9396(8) 0.165(4) Uani 0.5 1 d . . P . .


_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
N2 C23 1.371(3) . ?
N2 C8 1.385(3) . ?
N2 C15 1.467(3) . ?
N1 C23 1.320(3) . ?
N1 C1 1.376(3) . ?
C8 C1 1.376(3) . ?
C8 C9 1.484(3) . ?
C1 C2 1.477(3) . ?
C16 C17 1.379(3) . ?
C16 C21 1.389(3) . ?
C16 C15 1.509(3) . ?
C23 C24 1.475(3) . ?
C24 C29 1.391(3) . ?
C24 C25 1.400(3) . ?
C17 C18 1.374(3) . ?
C9 C14 1.378(3) . ?
C9 C10 1.381(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.392(3) . ?
C19 C20 1.385(4) . ?
C19 C18 1.387(3) . ?
C19 C22 1.441(4) . ?
C25 C26 1.378(3) . ?
C29 C28 1.377(3) . ?
C27 C26 1.385(4) . ?
C27 C28 1.390(3) . ?
C27 C30 1.440(4) . ?
C21 C20 1.378(4) . ?
C7 C6 1.384(4) . ?
C3 C4 1.385(4) . ?
C14 C13 1.388(4) . ?
C10 C11 1.387(4) . ?
C30 N3 1.145(4) . ?
N4 C22 1.135(4) . ?
C6 C5 1.361(4) . ?
C4 C5 1.381(4) . ?
C11 C12 1.360(5) . ?
C13 C12 1.377(5) . ?
C31 C31 1.724(13) 2_577 ?

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
C23 N2 C8 107.04(17) . . ?
C23 N2 C15 128.69(18) . . ?
C8 N2 C15 123.93(18) . . ?
C23 N1 C1 106.15(17) . . ?
C1 C8 N2 105.55(18) . . ?
C1 C8 C9 133.0(2) . . ?
N2 C8 C9 121.19(19) . . ?
C8 C1 N1 110.08(19) . . ?
C8 C1 C2 129.1(2) . . ?
N1 C1 C2 120.81(19) . . ?
C17 C16 C21 118.6(2) . . ?
C17 C16 C15 121.67(19) . . ?
C21 C16 C15 119.7(2) . . ?
N1 C23 N2 111.18(18) . . ?
N1 C23 C24 123.13(19) . . ?
N2 C23 C24 125.70(19) . . ?
C29 C24 C25 118.3(2) . . ?
C29 C24 C23 122.6(2) . . ?
C25 C24 C23 119.0(2) . . ?
C18 C17 C16 121.1(2) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C8 122.2(2) . . ?
C10 C9 C8 119.4(2) . . ?
C7 C2 C3 118.0(2) . . ?
C7 C2 C1 120.2(2) . . ?
C3 C2 C1 121.8(2) . . ?
N2 C15 C16 113.08(17) . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 C22 120.1(2) . . ?
C18 C19 C22 120.0(3) . . ?
C26 C25 C24 121.0(2) . . ?
C28 C29 C24 121.1(2) . . ?
C26 C27 C28 120.0(2) . . ?
C26 C27 C30 120.0(2) . . ?
C28 C27 C30 119.9(2) . . ?
C17 C18 C19 119.8(2) . . ?
C25 C26 C27 119.8(2) . . ?
C20 C21 C16 121.1(2) . . ?
C29 C28 C27 119.8(2) . . ?
C6 C7 C2 120.6(3) . . ?
C4 C3 C2 120.7(3) . . ?
C9 C14 C13 120.8(3) . . ?
C21 C20 C19 119.4(2) . . ?
C9 C10 C11 120.8(3) . . ?
N3 C30 C27 179.7(4) . . ?
N4 C22 C19 178.6(4) . . ?
C5 C6 C7 121.0(3) . . ?
C5 C4 C3 120.4(3) . . ?
C6 C5 C4 119.4(3) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C13 C14 119.6(3) . . ?
C11 C12 C13 120.2(3) . . ?

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.069

