# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_rs_bg_8001_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2004156'
_audit_update_record             
;
2020-05-15 deposited with the CCDC.	2021-11-09 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         'C33 H27 N O5'
_chemical_formula_sum            'C33 H27 N O5'
_chemical_formula_weight         517.55

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                   8.649(4)
_cell_length_b                   11.578(5)
_cell_length_c                   13.602(7)
_cell_angle_alpha                89.58(5)
_cell_angle_beta                 77.17(3)
_cell_angle_gamma                77.71(4)
_cell_volume                     1296.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10966
_cell_measurement_theta_min      2.319
_cell_measurement_theta_max      36.547

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex-3 CCD'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27368
_diffrn_reflns_av_unetI/netI     0.1542
_diffrn_reflns_av_R_equivalents  0.1309
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         36.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             10966
_reflns_number_gt                3722
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.1323P)²+0.5217P] 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       0.014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10966
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2485
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.3292
_refine_ls_wR_factor_gt          0.2207
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_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
O2 O 0.5217(3) 0.3567(2) 0.02176(16) 0.0656(6) Uani 1 1 d . . . . .
O3 O 0.5185(2) 0.3597(2) 0.18702(14) 0.0590(6) Uani 1 1 d . . . . .
O5 O 0.5304(3) 0.76875(18) 0.26147(16) 0.0603(5) Uani 1 1 d . . . . .
O4 O 0.3241(3) 0.5800(2) 0.29622(17) 0.0685(6) Uani 1 1 d . . . . .
N1 N 0.9575(3) 0.3353(2) 0.24954(19) 0.0516(6) Uani 1 1 d . . . . .
C17 C 0.8030(3) 0.4843(2) 0.16444(19) 0.0440(6) Uani 1 1 d . . . . .
C18 C 0.8560(3) 0.4440(2) 0.25395(19) 0.0430(5) Uani 1 1 d . . . . .
C22 C 0.7991(3) 0.5168(2) 0.34425(19) 0.0437(5) Uani 1 1 d . . . . .
C24 C 0.6240(3) 0.7041(2) 0.44079(19) 0.0468(6) Uani 1 1 d . . . . .
C9 C 0.5922(3) 0.3421(2) 0.08901(19) 0.0459(6) Uani 1 1 d . . . . .
C33 C 0.6878(3) 0.8052(2) 0.4556(2) 0.0469(6) Uani 1 1 d . . . . .
C15 C 0.6976(4) 0.5907(2) 0.1687(2) 0.0486(6) Uani 1 1 d . . . . .
H15 H 0.663241 0.617397 0.110841 0.058 Uiso 1 1 calc R U . . .
C23 C 0.6888(3) 0.6282(2) 0.34621(19) 0.0441(5) Uani 1 1 d . . . . .
C8 C 0.7746(3) 0.3017(2) 0.07583(18) 0.0444(6) Uani 1 1 d . . . . .
H8 H 0.796373 0.257171 0.134620 0.053 Uiso 1 1 calc R U . . .
C7 C 0.8398(4) 0.2189(3) -0.0183(2) 0.0502(6) Uani 1 1 d . . . . .
C32 C 0.8091(4) 0.8412(3) 0.3810(2) 0.0587(8) Uani 1 1 d . . . . .
H32 H 0.850525 0.798093 0.319922 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8570(4) 0.4078(2) 0.0684(2) 0.0496(6) Uani 1 1 d . . . . .
H16A H 0.973831 0.379136 0.054397 0.059 Uiso 1 1 calc R U . . .
H16B H 0.831032 0.455087 0.012731 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6388(4) 0.6620(2) 0.2591(2) 0.0472(6) Uani 1 1 d . . . . .
C6 C 0.8000(4) 0.0989(3) -0.0124(2) 0.0554(7) Uani 1 1 d . . . . .
C19 C 1.0022(4) 0.2977(3) 0.3333(3) 0.0586(7) Uani 1 1 d . . . . .
H19 H 1.070783 0.223514 0.330662 0.070 Uiso 1 1 calc R U . . .
C21 C 0.8527(4) 0.4712(3) 0.4309(2) 0.0531(7) Uani 1 1 d . . . . .
H21 H 0.819464 0.515724 0.491508 0.064 Uiso 1 1 calc R U . . .
C25 C 0.5028(4) 0.6773(3) 0.5144(2) 0.0603(8) Uani 1 1 d . . . . .
H25 H 0.461137 0.611669 0.504649 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3843(4) 0.7666(3) 0.2284(2) 0.0623(8) Uani 1 1 d . . . . .
H13A H 0.412992 0.726687 0.162347 0.075 Uiso 1 1 calc R U . . .
H13B H 0.328078 0.847193 0.221772 0.075 Uiso 1 1 calc R U . . .
C28 C 0.6244(4) 0.8741(3) 0.5472(2) 0.0554(7) Uani 1 1 d . . . . .
C20 C 0.9528(4) 0.3624(3) 0.4254(3) 0.0606(8) Uani 1 1 d . . . . .
H20 H 0.987893 0.331630 0.481959 0.073 Uiso 1 1 calc R U . . .
C11 C 0.2859(4) 0.5252(3) 0.2130(3) 0.0683(9) Uani 1 1 d . . . . .
H11A H 0.337904 0.554579 0.150046 0.082 Uiso 1 1 calc R U . . .
H11B H 0.169502 0.544476 0.218502 0.082 Uiso 1 1 calc R U . . .
C12 C 0.2720(5) 0.7056(3) 0.2989(3) 0.0735(10) Uani 1 1 d . . . . .
H12A H 0.259684 0.735916 0.367127 0.088 Uiso 1 1 calc R U . . .
H12B H 0.166049 0.725213 0.282622 0.088 Uiso 1 1 calc R U . . .
C31 C 0.8650(5) 0.9390(3) 0.3985(3) 0.0773(11) Uani 1 1 d . . . . .
H31 H 0.945511 0.961518 0.349601 0.093 Uiso 1 1 calc R U . . .
C27 C 0.4996(5) 0.8417(4) 0.6209(2) 0.0741(10) Uani 1 1 d . . . . .
H27 H 0.458015 0.886204 0.681221 0.089 Uiso 1 1 calc R U . . .
C1 C 0.8641(5) 0.0204(3) -0.0954(3) 0.0749(10) Uani 1 1 d . . . . .
H1 H 0.929584 0.042763 -0.153074 0.090 Uiso 1 1 calc R U . . .
C29 C 0.6865(5) 0.9750(3) 0.5608(3) 0.0742(10) Uani 1 1 d . . . . .
H29 H 0.646115 1.020821 0.620564 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3434(4) 0.3961(3) 0.2136(3) 0.0668(9) Uani 1 1 d . . . . .
H10A H 0.303482 0.369242 0.280288 0.080 Uiso 1 1 calc R U . . .
H10B H 0.298623 0.358427 0.166243 0.080 Uiso 1 1 calc R U . . .
C26 C 0.4400(5) 0.7461(4) 0.6042(3) 0.0744(10) Uani 1 1 d . . . . .
H26 H 0.356807 0.726126 0.652752 0.089 Uiso 1 1 calc R U . . .
C5 C 0.7063(5) 0.0614(3) 0.0716(3) 0.0784(11) Uani 1 1 d . . . . .
H5 H 0.663579 0.112248 0.128281 0.094 Uiso 1 1 calc R U . . .
C30 C 0.8025(5) 1.0057(3) 0.4892(4) 0.0816(12) Uani 1 1 d . . . . .
H30 H 0.841925 1.072173 0.500032 0.098 Uiso 1 1 calc R U . . .
C2 C 0.8295(7) -0.0922(4) -0.0919(4) 0.0997(16) Uani 1 1 d . . . . .
H2 H 0.872221 -0.144839 -0.147395 0.120 Uiso 1 1 calc R U . . .
C4 C 0.6743(7) -0.0504(4) 0.0734(4) 0.1045(16) Uani 1 1 d . . . . .
H4 H 0.611080 -0.074057 0.131410 0.125 Uiso 1 1 calc R U . . .
C3 C 0.7333(7) -0.1254(4) -0.0074(5) 0.1096(17) Uani 1 1 d . . . . .
H3 H 0.708730 -0.199883 -0.005871 0.131 Uiso 1 1 calc R U . . .
O1 O 0.9196(3) 0.2501(2) -0.09429(16) 0.0722(7) 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
O2 C9 1.199(3) . ?
O3 C9 1.340(3) . ?
O3 C10 1.446(4) . ?
O5 C14 1.379(3) . ?
O5 C13 1.438(4) . ?
O4 C12 1.426(4) . ?
O4 C11 1.435(4) . ?
N1 C19 1.324(4) . ?
N1 C18 1.366(4) . ?
C17 C15 1.361(4) . ?
C17 C18 1.435(4) . ?
C17 C16 1.509(4) . ?
C18 C22 1.425(4) . ?
C22 C21 1.419(4) . ?
C22 C23 1.428(4) . ?
C24 C25 1.366(4) . ?
C24 C33 1.429(4) . ?
C24 C23 1.493(4) . ?
C9 C8 1.517(4) . ?
C33 C32 1.418(4) . ?
C33 C28 1.419(4) . ?
C15 C14 1.417(4) . ?
C15 H15 0.9300 . ?
C23 C14 1.376(4) . ?
C8 C7 1.531(4) . ?
C8 C16 1.537(4) . ?
C8 H8 0.9800 . ?
C7 O1 1.208(3) . ?
C7 C6 1.498(4) . ?
C32 C31 1.365(4) . ?
C32 H32 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 C5 1.372(5) . ?
C6 C1 1.390(4) . ?
C19 C20 1.398(5) . ?
C19 H19 0.9300 . ?
C21 C20 1.360(4) . ?
C21 H21 0.9300 . ?
C25 C26 1.398(5) . ?
C25 H25 0.9300 . ?
C13 C12 1.493(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C28 C27 1.414(5) . ?
C28 C29 1.415(5) . ?
C20 H20 0.9300 . ?
C11 C10 1.472(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C31 C30 1.397(5) . ?
C31 H31 0.9300 . ?
C27 C26 1.357(5) . ?
C27 H27 0.9300 . ?
C1 C2 1.396(6) . ?
C1 H1 0.9300 . ?
C29 C30 1.340(6) . ?
C29 H29 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C26 H26 0.9300 . ?
C5 C4 1.379(5) . ?
C5 H5 0.9300 . ?
C30 H30 0.9300 . ?
C2 C3 1.367(7) . ?
C2 H2 0.9300 . ?
C4 C3 1.341(7) . ?
C4 H4 0.9300 . ?
C3 H3 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
C9 O3 C10 118.2(2) . . ?
C14 O5 C13 116.7(2) . . ?
C12 O4 C11 111.8(3) . . ?
C19 N1 C18 117.7(3) . . ?
C15 C17 C18 118.8(2) . . ?
C15 C17 C16 120.4(3) . . ?
C18 C17 C16 120.7(3) . . ?
N1 C18 C22 122.4(3) . . ?
N1 C18 C17 118.2(2) . . ?
C22 C18 C17 119.4(3) . . ?
C21 C22 C18 116.9(3) . . ?
C21 C22 C23 122.6(2) . . ?
C18 C22 C23 120.5(2) . . ?
C25 C24 C33 119.2(3) . . ?
C25 C24 C23 120.2(3) . . ?
C33 C24 C23 120.6(2) . . ?
O2 C9 O3 123.9(3) . . ?
O2 C9 C8 125.3(2) . . ?
O3 C9 C8 110.7(2) . . ?
C32 C33 C28 118.7(3) . . ?
C32 C33 C24 122.4(2) . . ?
C28 C33 C24 118.9(3) . . ?
C17 C15 C14 121.7(3) . . ?
C17 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C14 C23 C22 118.1(2) . . ?
C14 C23 C24 120.6(3) . . ?
C22 C23 C24 121.3(2) . . ?
C9 C8 C7 108.1(2) . . ?
C9 C8 C16 111.2(2) . . ?
C7 C8 C16 111.7(2) . . ?
C9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C16 C8 H8 108.6 . . ?
O1 C7 C6 121.7(3) . . ?
O1 C7 C8 120.8(3) . . ?
C6 C7 C8 117.5(2) . . ?
C31 C32 C33 120.1(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C17 C16 C8 111.9(2) . . ?
C17 C16 H16A 109.2 . . ?
C8 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C8 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C23 C14 O5 118.0(2) . . ?
C23 C14 C15 121.5(3) . . ?
O5 C14 C15 120.4(2) . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C7 123.4(3) . . ?
C1 C6 C7 118.4(3) . . ?
N1 C19 C20 124.1(3) . . ?
N1 C19 H19 117.9 . . ?
C20 C19 H19 117.9 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C24 C25 C26 121.6(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
O5 C13 C12 113.0(3) . . ?
O5 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
O5 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C27 C28 C29 122.0(3) . . ?
C27 C28 C33 119.4(3) . . ?
C29 C28 C33 118.6(3) . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O4 C11 C10 109.4(3) . . ?
O4 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
O4 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O4 C12 C13 114.4(3) . . ?
O4 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
O4 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C32 C31 C30 120.7(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C6 C1 C2 119.7(4) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C30 C29 C28 121.2(3) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
O3 C10 C11 112.6(3) . . ?
O3 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
O3 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C29 C30 C31 120.7(3) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.076

