# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2058231'
loop_
_audit_author_name
_audit_author_address
'He Zhao'
;South China University of Technology
China
;
_audit_update_record             
;
2021-01-23 deposited with the CCDC.	2021-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2206(6)
_cell_length_b                   18.2032(13)
_cell_length_c                   18.9733(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.680(7)
_cell_angle_gamma                90
_cell_volume                     2141.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4919
_cell_measurement_theta_min      2.154
_cell_measurement_theta_max      29.383

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9648
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.154
_diffrn_reflns_theta_max         29.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4919
_reflns_number_gt                2958
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0573P)²+0.2165P] 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         4919
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.5427(3) 0.72982(9) 0.45218(9) 0.0330(4) Uani 1 1 d . . . . .
C1 C 0.4706(4) 0.79993(11) 0.42810(11) 0.0317(5) Uani 1 1 d . . . . .
H1A H 0.5890 0.8248 0.4067 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3945(4) 0.84849(10) 0.48611(11) 0.0300(5) Uani 1 1 d . . . . .
C3 C 0.2182(4) 0.80816(11) 0.52200(11) 0.0357(6) Uani 1 1 d . . . . .
H3A H 0.2013 0.8311 0.5673 0.043 Uiso 1 1 calc R U . . .
H3B H 0.0829 0.8135 0.4932 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2631(4) 0.72755(11) 0.53362(11) 0.0338(5) Uani 1 1 d . . . . .
C5 C 0.1429(4) 0.68762(14) 0.57879(13) 0.0516(7) Uani 1 1 d . . . . .
H5A H 0.0335 0.7112 0.6006 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1805(6) 0.61438(16) 0.59223(15) 0.0685(9) Uani 1 1 d . . . . .
H6A H 0.0968 0.5887 0.6223 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3427(6) 0.57982(14) 0.56080(15) 0.0678(9) Uani 1 1 d . . . . .
H7A H 0.3720 0.5306 0.5705 0.081 Uiso 1 1 calc R U . . .
C8 C 0.4629(5) 0.61726(12) 0.51491(13) 0.0530(7) Uani 1 1 d . . . . .
H8A H 0.5721 0.5929 0.4936 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4231(4) 0.69156(11) 0.49974(11) 0.0347(5) Uani 1 1 d . . . . .
C10 C 0.7341(4) 0.69737(13) 0.42594(13) 0.0430(6) Uani 1 1 d . . . . .
H10A H 0.8172 0.6746 0.4656 0.052 Uiso 1 1 calc R U . . .
H10B H 0.8212 0.7368 0.4090 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7005(4) 0.64062(11) 0.36741(13) 0.0417(6) Uani 1 1 d . . . . .
C12 C 0.8749(5) 0.59841(13) 0.35139(15) 0.0580(8) Uani 1 1 d . . . . .
H12A H 1.0050 0.6023 0.3789 0.070 Uiso 1 1 calc R U . . .
C13 C 0.8568(7) 0.55033(15) 0.29449(19) 0.0774(11) Uani 1 1 d . . . . .
H13A H 0.9751 0.5224 0.2838 0.093 Uiso 1 1 calc R U . . .
C14 C 0.6650(7) 0.54391(16) 0.25393(18) 0.0813(11) Uani 1 1 d . . . . .
H14A H 0.6540 0.5124 0.2153 0.098 Uiso 1 1 calc R U . . .
C15 C 0.4910(6) 0.58368(16) 0.27027(16) 0.0729(9) Uani 1 1 d . . . . .
H15A H 0.3599 0.5785 0.2435 0.087 Uiso 1 1 calc R U . . .
C16 C 0.5092(5) 0.63217(14) 0.32719(14) 0.0562(7) Uani 1 1 d . . . . .
H16A H 0.3895 0.6593 0.3380 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5855(4) 0.86437(12) 0.53959(12) 0.0404(6) Uani 1 1 d . . . . .
H17A H 0.5418 0.8979 0.5755 0.048 Uiso 1 1 calc R U . . .
H17B H 0.6345 0.8191 0.5627 0.048 Uiso 1 1 calc R U . . .
C18 C 0.3100(4) 0.92114(11) 0.45373(12) 0.0361(6) Uani 1 1 d . . . . .
H18A H 0.2404 0.9491 0.4890 0.043 Uiso 1 1 calc R U . . .
H18B H 0.4299 0.9499 0.4391 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1522(4) 0.90725(11) 0.39119(11) 0.0320(5) Uani 1 1 d . . . . .
C20 C 0.1507(4) 0.84255(11) 0.35642(11) 0.0331(5) Uani 1 1 d . . . . .
C21 C -0.0126(4) 0.82603(12) 0.30024(11) 0.0366(6) Uani 1 1 d . . . . .
C22 C -0.0269(4) 0.75940(13) 0.26324(12) 0.0461(7) Uani 1 1 d . . . . .
H22A H 0.0785 0.7236 0.2722 0.055 Uiso 1 1 calc R U . . .
C23 C -0.1963(5) 0.74690(15) 0.21368(13) 0.0567(8) Uani 1 1 d . . . . .
H23A H -0.2066 0.7022 0.1899 0.068 Uiso 1 1 calc R U . . .
C24 C -0.3514(5) 0.80007(16) 0.19884(14) 0.0639(8) Uani 1 1 d . . . . .
H24A H -0.4648 0.7910 0.1649 0.077 Uiso 1 1 calc R U . . .
C25 C -0.3398(5) 0.86633(15) 0.23368(14) 0.0588(8) Uani 1 1 d . . . . .
H25A H -0.4438 0.9023 0.2235 0.071 Uiso 1 1 calc R U . . .
C26 C -0.1702(4) 0.87839(13) 0.28421(12) 0.0413(6) Uani 1 1 d . . . . .
C27 C -0.0080(4) 0.96169(12) 0.37144(11) 0.0360(5) Uani 1 1 d . . . . .
O1 O 0.7551(3) 0.89589(9) 0.50441(9) 0.0523(5) Uani 1 1 d . . . . .
H1B H 0.8338 0.9196 0.5327 0.078 Uiso 1 1 calc R U . . .
O2 O -0.0199(3) 1.02269(8) 0.39692(9) 0.0478(5) Uani 1 1 d . . . . .
O3 O -0.1659(3) 0.94515(8) 0.31859(8) 0.0465(4) Uani 1 1 d . . . . .
O4 O 0.2907(3) 0.78760(8) 0.37231(7) 0.0397(4) 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
N1 C9 1.401(3) . ?
N1 C1 1.416(3) . ?
N1 C10 1.453(3) . ?
C1 O4 1.493(2) . ?
C1 C2 1.517(3) . ?
C2 C3 1.525(3) . ?
C2 C17 1.526(3) . ?
C2 C18 1.533(3) . ?
C3 C4 1.507(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.374(4) . ?
C6 C7 1.367(4) . ?
C7 C8 1.374(4) . ?
C8 C9 1.401(3) . ?
C10 C11 1.519(3) . ?
C11 C16 1.369(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.387(4) . ?
C13 C14 1.371(5) . ?
C14 C15 1.359(4) . ?
C15 C16 1.392(3) . ?
C17 O1 1.415(3) . ?
C18 C19 1.498(3) . ?
C19 C20 1.349(3) . ?
C19 C27 1.434(3) . ?
C20 O4 1.345(2) . ?
C20 C21 1.443(3) . ?
C21 C26 1.383(3) . ?
C21 C22 1.401(3) . ?
C22 C23 1.373(3) . ?
C23 C24 1.379(4) . ?
C24 C25 1.374(4) . ?
C25 C26 1.384(3) . ?
C26 O3 1.378(3) . ?
C27 O2 1.216(2) . ?
C27 O3 1.379(3) . ?

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 119.01(18) . . ?
C9 N1 C10 120.78(18) . . ?
C1 N1 C10 120.18(18) . . ?
N1 C1 O4 107.00(16) . . ?
N1 C1 C2 113.61(17) . . ?
O4 C1 C2 109.99(17) . . ?
C1 C2 C3 108.76(16) . . ?
C1 C2 C17 108.70(18) . . ?
C3 C2 C17 110.09(18) . . ?
C1 C2 C18 109.21(17) . . ?
C3 C2 C18 111.01(18) . . ?
C17 C2 C18 109.03(17) . . ?
C4 C3 C2 113.74(18) . . ?
C5 C4 C9 118.7(2) . . ?
C5 C4 C3 119.9(2) . . ?
C9 C4 C3 121.5(2) . . ?
C4 C5 C6 122.0(3) . . ?
C7 C6 C5 119.1(3) . . ?
C8 C7 C6 120.5(2) . . ?
C7 C8 C9 120.9(3) . . ?
N1 C9 C4 120.06(18) . . ?
N1 C9 C8 121.2(2) . . ?
C4 C9 C8 118.7(2) . . ?
N1 C10 C11 117.3(2) . . ?
C16 C11 C12 118.5(2) . . ?
C16 C11 C10 123.1(2) . . ?
C12 C11 C10 118.4(2) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 120.1(3) . . ?
C13 C14 C15 120.0(3) . . ?
C14 C15 C16 119.9(3) . . ?
C11 C16 C15 121.1(3) . . ?
O1 C17 C2 109.46(18) . . ?
C19 C18 C2 110.66(17) . . ?
C20 C19 C27 119.9(2) . . ?
C20 C19 C18 120.84(19) . . ?
C27 C19 C18 119.14(18) . . ?
O4 C20 C19 124.1(2) . . ?
O4 C20 C21 114.51(18) . . ?
C19 C20 C21 121.3(2) . . ?
C26 C21 C22 118.1(2) . . ?
C26 C21 C20 117.5(2) . . ?
C22 C21 C20 124.3(2) . . ?
C23 C22 C21 120.0(2) . . ?
C22 C23 C24 120.6(2) . . ?
C25 C24 C23 120.6(3) . . ?
C26 C25 C24 118.6(3) . . ?
C21 C26 C25 122.0(2) . . ?
C21 C26 O3 121.2(2) . . ?
C25 C26 O3 116.9(2) . . ?
O2 C27 O3 115.2(2) . . ?
O2 C27 C19 126.2(2) . . ?
O3 C27 C19 118.57(19) . . ?
C27 O3 C26 121.46(18) . . ?
C20 O4 C1 118.79(15) . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044

