# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_0314zyy210921_0m
_database_code_depnum_ccdc_archive 'CCDC 2159416'
loop_
_audit_author_name
_audit_author_address
'youya zhang' 'Wuyi University'
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N O4'
_chemical_formula_sum            'C28 H21 N O4'
_chemical_formula_weight         435.46
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1241(6)
_cell_length_b                   12.2852(5)
_cell_length_c                   14.9183(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.870(2)
_cell_angle_gamma                90
_cell_volume                     2195.46(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    160
_cell_measurement_theta_max      24.933
_cell_measurement_theta_min      2.612
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1023 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.9109. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      160.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2631
_reflns_number_total             4472
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.069
_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)+(0.0486P)²+0.3706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C11(H11), C18(H18), C19(H19), C23(H23), C00L(H00L), C7(H7),
 C24(H24), C16(H16), C15(H15), C6(H6), C14(H14), C13(H13), C5(H5), C3(H3),
 C4(H4)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.33408(14) 0.35425(13) 0.41580(11) 0.0347(4) Uani 1 1 d . . . . .
O2 O 0.24567(15) 0.17188(14) 0.30693(11) 0.0433(5) Uani 1 1 d . . . . .
O1 O 0.18871(15) 0.13707(15) 0.44002(12) 0.0475(5) Uani 1 1 d . . . . .
O4 O 0.69697(15) 0.11386(14) 0.52709(13) 0.0469(5) Uani 1 1 d . . . . .
N1 N 0.57678(16) 0.14713(15) 0.65963(12) 0.0286(5) Uani 1 1 d . . . . .
C20 C 0.42160(19) 0.21859(18) 0.51401(15) 0.0271(5) Uani 1 1 d . . . . .
C21 C 0.41994(19) 0.11431(18) 0.54317(15) 0.0278(6) Uani 1 1 d . . . . .
H21 H 0.368580 0.064415 0.510919 0.033 Uiso 1 1 calc R . . . .
C26 C 0.34059(19) 0.25850(18) 0.44089(15) 0.0259(5) Uani 1 1 d . . . . .
C10 C 0.44970(19) 0.37143(18) 0.62930(15) 0.0256(5) Uani 1 1 d . . . . .
C9 C 0.50275(18) 0.30066(17) 0.56327(15) 0.0260(5) Uani 1 1 d . . . . .
H9 H 0.526616 0.349996 0.516512 0.031 Uiso 1 1 calc R . . . .
C17 C 0.3622(2) 0.4989(2) 0.75981(16) 0.0316(6) Uani 1 1 d . . . . .
C11 C 0.4842(2) 0.47686(18) 0.64527(16) 0.0311(6) Uani 1 1 d . . . . .
H11 H 0.536732 0.506906 0.611029 0.037 Uiso 1 1 calc R . . . .
C18 C 0.3240(2) 0.3922(2) 0.73903(16) 0.0346(6) Uani 1 1 d . . . . .
H18 H 0.266550 0.362976 0.768515 0.042 Uiso 1 1 calc R . . . .
C8 C 0.60900(19) 0.24279(18) 0.61276(16) 0.0282(6) Uani 1 1 d . . . . .
H8 H 0.649238 0.294009 0.658675 0.034 Uiso 1 1 calc R . . . .
C27 C 0.2548(2) 0.18235(19) 0.38779(17) 0.0313(6) Uani 1 1 d . . . . .
C19 C 0.3678(2) 0.3300(2) 0.67746(16) 0.0328(6) Uani 1 1 d . . . . .
H19 H 0.342579 0.257294 0.666876 0.039 Uiso 1 1 calc R . . . .
C22 C 0.4926(2) 0.07814(19) 0.62025(16) 0.0294(6) Uani 1 1 d . . . . .
C2 C 0.7551(2) 0.29364(19) 0.50691(16) 0.0313(6) Uani 1 1 d . . . . .
C12 C 0.4438(2) 0.54250(18) 0.71158(16) 0.0308(6) Uani 1 1 d . . . . .
C23 C 0.4969(2) -0.01433(19) 0.67371(16) 0.0348(6) Uani 1 1 d . . . . .
H23 H 0.448476 -0.075403 0.663633 0.042 Uiso 1 1 calc R . . . .
C00L C 0.6341(2) 0.0976(2) 0.73444(16) 0.0350(6) Uani 1 1 d . . . . .
H00L H 0.697177 0.126476 0.772731 0.042 Uiso 1 1 calc R . . . .
C1 C 0.68879(19) 0.20963(19) 0.54624(16) 0.0321(6) Uani 1 1 d . . . . .
C7 C 0.7541(2) 0.4035(2) 0.52849(17) 0.0351(6) Uani 1 1 d . . . . .
H7 H 0.710037 0.427981 0.571920 0.042 Uiso 1 1 calc R . . . .
C24 C 0.5848(2) -0.0017(2) 0.74490(17) 0.0381(6) Uani 1 1 d . . . . .
H24 H 0.606798 -0.052534 0.792277 0.046 Uiso 1 1 calc R . . . .
C16 C 0.3274(2) 0.5622(2) 0.83007(17) 0.0392(7) Uani 1 1 d . . . . .
H16 H 0.272335 0.534254 0.862802 0.047 Uiso 1 1 calc R . . . .
C15 C 0.3719(2) 0.6621(2) 0.85108(18) 0.0423(7) Uani 1 1 d . . . . .
H15 H 0.349130 0.702692 0.899275 0.051 Uiso 1 1 calc R . . . .
C6 C 0.8160(2) 0.4775(2) 0.48790(18) 0.0430(7) Uani 1 1 d . . . . .
H6 H 0.814147 0.552491 0.503233 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4859(3) 0.6483(2) 0.73378(19) 0.0477(8) Uani 1 1 d . . . . .
H14 H 0.539023 0.679516 0.700712 0.057 Uiso 1 1 calc R . . . .
C13 C 0.4507(3) 0.7055(2) 0.80228(19) 0.0493(8) Uani 1 1 d . . . . .
H13 H 0.480306 0.775960 0.817007 0.059 Uiso 1 1 calc R . . . .
C5 C 0.8804(3) 0.4432(2) 0.4254(2) 0.0533(8) Uani 1 1 d . . . . .
H5 H 0.922658 0.494321 0.397130 0.064 Uiso 1 1 calc R . . . .
C3 C 0.8216(3) 0.2604(2) 0.4439(2) 0.0525(8) Uani 1 1 d . . . . .
H3 H 0.824226 0.185549 0.428366 0.063 Uiso 1 1 calc R . . . .
C4 C 0.8835(3) 0.3345(3) 0.4038(2) 0.0658(10) Uani 1 1 d . . . . .
H4 H 0.928664 0.310623 0.360981 0.079 Uiso 1 1 calc R . . . .
C28 C 0.0992(3) 0.0689(3) 0.3937(2) 0.0742(11) Uani 1 1 d . . . . .
H28A H 0.053585 0.111260 0.346155 0.111 Uiso 1 1 calc GR . . . .
H28B H 0.052475 0.043298 0.437528 0.111 Uiso 1 1 calc GR . . . .
H28C H 0.131416 0.006164 0.366461 0.111 Uiso 1 1 calc GR . . . .


_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
O3 C26 1.233(3) . ?
O2 C27 1.201(3) . ?
O1 C27 1.324(3) . ?
O1 C28 1.458(3) . ?
O4 C1 1.218(3) . ?
N1 C8 1.452(3) . ?
N1 C22 1.385(3) . ?
N1 C00L 1.364(3) . ?
C20 C21 1.354(3) . ?
C20 C26 1.437(3) . ?
C20 C9 1.517(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.409(3) . ?
C26 C27 1.526(3) . ?
C10 C9 1.528(3) . ?
C10 C11 1.371(3) . ?
C10 C19 1.407(3) . ?
C9 H9 1.0000 . ?
C9 C8 1.555(3) . ?
C17 C18 1.408(3) . ?
C17 C12 1.415(3) . ?
C17 C16 1.420(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.421(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(3) . ?
C8 H8 1.0000 . ?
C8 C1 1.544(3) . ?
C19 H19 0.9500 . ?
C22 C23 1.384(3) . ?
C2 C1 1.484(3) . ?
C2 C7 1.388(3) . ?
C2 C3 1.390(4) . ?
C12 C14 1.417(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(3) . ?
C00L H00L 0.9500 . ?
C00L C24 1.378(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.378(3) . ?
C24 H24 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.358(4) . ?
C15 H15 0.9500 . ?
C15 C13 1.393(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.371(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.362(4) . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
C27 O1 C28 115.9(2) . . ?
C22 N1 C8 121.76(19) . . ?
C00L N1 C8 127.9(2) . . ?
C00L N1 C22 108.84(19) . . ?
C21 C20 C26 121.6(2) . . ?
C21 C20 C9 120.9(2) . . ?
C26 C20 C9 117.21(19) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.5(2) . . ?
C22 C21 H21 119.3 . . ?
O3 C26 C20 124.1(2) . . ?
O3 C26 C27 114.9(2) . . ?
C20 C26 C27 121.1(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 C19 118.3(2) . . ?
C19 C10 C9 121.6(2) . . ?
C20 C9 C10 112.61(18) . . ?
C20 C9 H9 107.5 . . ?
C20 C9 C8 110.74(18) . . ?
C10 C9 H9 107.5 . . ?
C10 C9 C8 110.76(18) . . ?
C8 C9 H9 107.5 . . ?
C18 C17 C12 118.2(2) . . ?
C18 C17 C16 123.2(2) . . ?
C12 C17 C16 118.6(2) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
N1 C8 C9 109.52(18) . . ?
N1 C8 H8 108.6 . . ?
N1 C8 C1 109.75(18) . . ?
C9 C8 H8 108.6 . . ?
C1 C8 C9 111.78(19) . . ?
C1 C8 H8 108.6 . . ?
O2 C27 O1 125.1(2) . . ?
O2 C27 C26 122.5(2) . . ?
O1 C27 C26 112.2(2) . . ?
C10 C19 H19 119.3 . . ?
C18 C19 C10 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
N1 C22 C21 118.7(2) . . ?
C23 C22 N1 107.4(2) . . ?
C23 C22 C21 133.8(2) . . ?
C7 C2 C1 124.0(2) . . ?
C7 C2 C3 118.0(2) . . ?
C3 C2 C1 118.0(2) . . ?
C17 C12 C11 118.8(2) . . ?
C17 C12 C14 118.9(2) . . ?
C14 C12 C11 122.2(2) . . ?
C22 C23 H23 126.2 . . ?
C22 C23 C24 107.7(2) . . ?
C24 C23 H23 126.2 . . ?
N1 C00L H00L 125.9 . . ?
N1 C00L C24 108.2(2) . . ?
C24 C00L H00L 125.9 . . ?
O4 C1 C8 119.2(2) . . ?
O4 C1 C2 120.7(2) . . ?
C2 C1 C8 120.2(2) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C23 C24 H24 126.1 . . ?
C00L C24 C23 107.9(2) . . ?
C00L C24 H24 126.1 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C13 120.3(2) . . ?
C13 C15 H15 119.8 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C12 C14 H14 119.8 . . ?
C13 C14 C12 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C13 H13 119.5 . . ?
C14 C13 C15 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C6 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
O1 C28 H28A 109.5 . . ?
O1 C28 H28B 109.5 . . ?
O1 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
