# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2285891'
loop_
_audit_author_name
_audit_author_address
'Qiang Zhao'
;Nanyang Normal University
China
;
_audit_update_record             
;
2023-08-01 deposited with the CCDC.	2023-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 O3'
_chemical_formula_weight         394.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6983(19)
_cell_length_b                   10.099(2)
_cell_length_c                   12.581(3)
_cell_angle_alpha                69.766(4)
_cell_angle_beta                 70.291(3)
_cell_angle_gamma                65.925(3)
_cell_volume                     1027.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1146
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.64

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5077
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3570
_reflns_number_gt                2153
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.2025(3) 0.8337(3) 0.1168(2) 0.0400(6) Uani 1 1 d . . .
O2 O 0.0917(2) 0.6877(2) 0.42284(16) 0.0678(6) Uani 1 1 d . . .
O3 O 0.1871(2) 0.9966(2) 0.29357(16) 0.0577(5) Uani 1 1 d . . .
C1 C 0.2466(2) 0.5514(3) 0.1628(2) 0.0422(6) Uani 1 1 d . . .
C18 C 0.2188(3) 0.9716(3) 0.0289(2) 0.0402(6) Uani 1 1 d . . .
C8 C 0.1401(3) 0.8278(3) 0.2311(2) 0.0395(6) Uani 1 1 d . . .
O1 O 0.3037(2) 0.6981(2) -0.02806(17) 0.0676(6) Uani 1 1 d . . .
C10 C 0.2569(3) 0.6938(3) 0.0756(2) 0.0459(7) Uani 1 1 d . . .
C7 C 0.1356(3) 0.6859(3) 0.3201(2) 0.0451(7) Uani 1 1 d . . .
C6 C 0.1887(3) 0.5481(3) 0.2810(2) 0.0412(6) Uani 1 1 d . . .
C21 C 0.2607(3) 1.2386(3) -0.1315(2) 0.0416(6) Uani 1 1 d . . .
C11 C 0.0893(3) 0.9589(3) 0.2844(2) 0.0407(6) Uani 1 1 d . . .
C20 C 0.3806(3) 1.1017(3) -0.1274(2) 0.0510(7) Uani 1 1 d . . .
H20A H 0.4767 1.0974 -0.1784 0.061 Uiso 1 1 calc R . .
C22 C 0.1203(3) 1.2365(3) -0.0535(2) 0.0483(7) Uani 1 1 d . . .
H22A H 0.0373 1.3255 -0.0542 0.058 Uiso 1 1 calc R . .
C23 C 0.0985(3) 1.1073(3) 0.0252(2) 0.0447(7) Uani 1 1 d . . .
H23A H 0.0024 1.1115 0.0762 0.054 Uiso 1 1 calc R . .
C19 C 0.3593(3) 0.9714(3) -0.0488(2) 0.0511(7) Uani 1 1 d . . .
H19A H 0.4416 0.8819 -0.0485 0.061 Uiso 1 1 calc R . .
C2 C 0.2952(3) 0.4224(3) 0.1266(3) 0.0576(8) Uani 1 1 d . . .
H2A H 0.3382 0.4227 0.0484 0.069 Uiso 1 1 calc R . .
C5 C 0.1802(3) 0.4153(3) 0.3613(2) 0.0531(7) Uani 1 1 d . . .
H5A H 0.1450 0.4122 0.4403 0.064 Uiso 1 1 calc R . .
C24 C 0.2825(3) 1.3807(3) -0.2209(2) 0.0484(7) Uani 1 1 d . . .
C12 C -0.0795(3) 1.0270(3) 0.3309(2) 0.0447(7) Uani 1 1 d . . .
C4 C 0.2242(3) 0.2872(3) 0.3234(3) 0.0600(8) Uani 1 1 d . . .
H4A H 0.2158 0.1988 0.3770 0.072 Uiso 1 1 calc R . .
C17 C -0.1286(3) 1.1176(3) 0.4072(2) 0.0516(7) Uani 1 1 d . . .
H17A H -0.0560 1.1363 0.4280 0.062 Uiso 1 1 calc R . .
C3 C 0.2797(3) 0.2904(3) 0.2083(3) 0.0649(9) Uani 1 1 d . . .
H3A H 0.3075 0.2044 0.1834 0.078 Uiso 1 1 calc R . .
C13 C -0.1897(3) 1.0010(3) 0.2994(2) 0.0601(8) Uani 1 1 d . . .
H13A H -0.1579 0.9393 0.2492 0.072 Uiso 1 1 calc R . .
C16 C -0.2845(4) 1.1798(3) 0.4521(2) 0.0672(9) Uani 1 1 d . . .
H16A H -0.3170 1.2384 0.5047 0.081 Uiso 1 1 calc R . .
C26 C 0.4415(3) 1.3905(4) -0.2349(3) 0.0801(11) Uani 1 1 d . . .
H26A H 0.4504 1.3920 -0.1617 0.120 Uiso 1 1 calc R . .
H26B H 0.4520 1.4802 -0.2918 0.120 Uiso 1 1 calc R . .
H26C H 0.5216 1.3053 -0.2601 0.120 Uiso 1 1 calc R . .
C27 C 0.1595(4) 1.5208(3) -0.1856(3) 0.0841(12) Uani 1 1 d . . .
H27A H 0.1678 1.5243 -0.1128 0.126 Uiso 1 1 calc R . .
H27B H 0.0584 1.5186 -0.1775 0.126 Uiso 1 1 calc R . .
H27C H 0.1749 1.6077 -0.2443 0.126 Uiso 1 1 calc R . .
C14 C -0.3462(3) 1.0672(4) 0.3429(3) 0.0770(10) Uani 1 1 d . . .
H14A H -0.4194 1.0519 0.3203 0.092 Uiso 1 1 calc R . .
C25 C 0.2669(4) 1.3771(4) -0.3380(3) 0.0879(12) Uani 1 1 d . . .
H25A H 0.3431 1.2887 -0.3609 0.132 Uiso 1 1 calc R . .
H25B H 0.2830 1.4639 -0.3965 0.132 Uiso 1 1 calc R . .
H25C H 0.1650 1.3765 -0.3295 0.132 Uiso 1 1 calc R . .
C15 C -0.3940(4) 1.1550(4) 0.4190(3) 0.0744(10) Uani 1 1 d . . .
H15A H -0.4994 1.1983 0.4486 0.089 Uiso 1 1 calc R . .


_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
C9 C8 1.349(3) . ?
C9 C18 1.478(3) . ?
C9 C10 1.503(4) . ?
O2 C7 1.221(3) . ?
O3 C11 1.207(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.395(3) . ?
C1 C10 1.494(4) . ?
C18 C19 1.383(3) . ?
C18 C23 1.389(3) . ?
C8 C7 1.489(3) . ?
C8 C11 1.518(3) . ?
O1 C10 1.219(3) . ?
C7 C6 1.470(4) . ?
C6 C5 1.386(3) . ?
C21 C22 1.388(3) . ?
C21 C20 1.395(3) . ?
C21 C24 1.529(3) . ?
C11 C12 1.486(3) . ?
C20 C19 1.391(4) . ?
C20 H20A 0.9300 . ?
C22 C23 1.385(3) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C19 H19A 0.9300 . ?
C2 C3 1.403(4) . ?
C2 H2A 0.9300 . ?
C5 C4 1.386(4) . ?
C5 H5A 0.9300 . ?
C24 C27 1.524(4) . ?
C24 C26 1.531(4) . ?
C24 C25 1.546(4) . ?
C12 C17 1.390(4) . ?
C12 C13 1.399(4) . ?
C4 C3 1.358(4) . ?
C4 H4A 0.9300 . ?
C17 C16 1.376(4) . ?
C17 H17A 0.9300 . ?
C3 H3A 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13A 0.9300 . ?
C16 C15 1.398(5) . ?
C16 H16A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C14 C15 1.368(5) . ?
C14 H14A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C15 H15A 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
C8 C9 C18 123.4(2) . . ?
C8 C9 C10 118.7(2) . . ?
C18 C9 C10 117.9(2) . . ?
C2 C1 C6 119.6(2) . . ?
C2 C1 C10 119.9(2) . . ?
C6 C1 C10 120.5(2) . . ?
C19 C18 C23 117.4(2) . . ?
C19 C18 C9 120.5(2) . . ?
C23 C18 C9 122.0(2) . . ?
C9 C8 C7 122.9(2) . . ?
C9 C8 C11 123.7(2) . . ?
C7 C8 C11 112.8(2) . . ?
O1 C10 C1 120.7(2) . . ?
O1 C10 C9 120.1(2) . . ?
C1 C10 C9 119.1(2) . . ?
O2 C7 C6 122.5(2) . . ?
O2 C7 C8 118.8(2) . . ?
C6 C7 C8 118.7(2) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C7 120.2(2) . . ?
C1 C6 C7 119.8(2) . . ?
C22 C21 C20 116.2(2) . . ?
C22 C21 C24 122.5(2) . . ?
C20 C21 C24 121.3(2) . . ?
O3 C11 C12 123.3(2) . . ?
O3 C11 C8 118.9(2) . . ?
C12 C11 C8 117.6(2) . . ?
C19 C20 C21 121.4(2) . . ?
C19 C20 H20A 119.3 . . ?
C21 C20 H20A 119.3 . . ?
C23 C22 C21 122.7(2) . . ?
C23 C22 H22A 118.6 . . ?
C21 C22 H22A 118.6 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 H23A 119.7 . . ?
C18 C23 H23A 119.7 . . ?
C18 C19 C20 121.7(2) . . ?
C18 C19 H19A 119.2 . . ?
C20 C19 H19A 119.2 . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C27 C24 C21 111.6(2) . . ?
C27 C24 C26 107.6(3) . . ?
C21 C24 C26 111.4(2) . . ?
C27 C24 C25 108.6(3) . . ?
C21 C24 C25 107.6(2) . . ?
C26 C24 C25 110.0(2) . . ?
C17 C12 C13 119.5(2) . . ?
C17 C12 C11 119.4(2) . . ?
C13 C12 C11 121.1(2) . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C16 C17 C12 120.0(3) . . ?
C16 C17 H17A 120.0 . . ?
C12 C17 H17A 120.0 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.055
