# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_o727_nyj
_database_code_depnum_ccdc_archive 'CCDC 2306968'
loop_
_audit_author_name
_audit_author_address
'Niu yj'
;xi an jiaotong  university
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 O3'
_chemical_formula_sum            'C23 H18 O3'
_chemical_formula_weight         342.37
_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'
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                   8.3943(12)
_cell_length_b                   11.8944(14)
_cell_length_c                   17.744(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.493(5)
_cell_angle_gamma                90
_cell_volume                     1768.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2443
_cell_measurement_temperature    302.00
_cell_measurement_theta_max      20.491
_cell_measurement_theta_min      2.625
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1497 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.6924.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28856
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.895
_diffrn_reflns_theta_min         2.062
_diffrn_ambient_temperature      302.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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                2300
_reflns_number_total             4638
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.033
_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)+(0.0701P)²+0.1432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1765
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
C1 C 0.0690(3) 0.3057(2) 0.08246(14) 0.0721(7) Uani 1 1 d . . . . .
H1 H 0.067289 0.261192 0.039317 0.087 Uiso 1 1 calc R U . . .
C2 C 0.1726(3) 0.28046(19) 0.14314(13) 0.0579(6) Uani 1 1 d . . . . .
H2 H 0.241507 0.219469 0.140951 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1738(2) 0.34576(16) 0.20686(11) 0.0458(5) Uani 1 1 d . . . . .
C4 C 0.0720(2) 0.43810(16) 0.21157(12) 0.0492(5) Uani 1 1 d . . . . .
C5 C -0.0304(3) 0.4615(2) 0.14901(14) 0.0650(6) Uani 1 1 d . . . . .
H5 H -0.099139 0.522717 0.150474 0.078 Uiso 1 1 calc R U . . .
C6 C -0.0323(3) 0.3964(3) 0.08523(15) 0.0762(8) Uani 1 1 d . . . . .
H6 H -0.101818 0.413426 0.043984 0.091 Uiso 1 1 calc R U . . .
C7 C 0.0858(3) 0.50530(17) 0.27933(13) 0.0544(5) Uani 1 1 d . . . . .
H7 H 0.035678 0.574972 0.280400 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1687(2) 0.46856(17) 0.33954(13) 0.0534(5) Uani 1 1 d . . . . .
H8 H 0.180965 0.514001 0.382151 0.064 Uiso 1 1 calc R U . . .
C9 C 0.2436(2) 0.35448(16) 0.34029(11) 0.0475(5) Uani 1 1 d . . . . .
C10 C 0.4008(2) 0.35467(19) 0.38730(13) 0.0590(6) Uani 1 1 d . . . . .
H10A H 0.382088 0.366276 0.440148 0.071 Uiso 1 1 calc R U . . .
H10B H 0.454917 0.283239 0.382326 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6204(2) 0.47818(19) 0.40529(12) 0.0522(5) Uani 1 1 d . . . . .
C12 C 0.7019(2) 0.57707(18) 0.37403(12) 0.0508(5) Uani 1 1 d . . . . .
C13 C 0.8236(2) 0.6277(2) 0.41773(13) 0.0581(6) Uani 1 1 d . . . . .
H13 H 0.855035 0.597987 0.464777 0.070 Uiso 1 1 calc R U . . .
C14 C 0.8986(3) 0.7222(2) 0.39185(15) 0.0678(7) Uani 1 1 d . . . . .
H14 H 0.979446 0.756390 0.421851 0.081 Uiso 1 1 calc R U . . .
C15 C 0.8548(3) 0.7658(2) 0.32250(15) 0.0697(7) Uani 1 1 d . . . . .
H15 H 0.905951 0.829277 0.305205 0.084 Uiso 1 1 calc R U . . .
C16 C 0.7352(3) 0.7156(2) 0.27840(15) 0.0691(7) Uani 1 1 d . . . . .
H16 H 0.705957 0.745015 0.230981 0.083 Uiso 1 1 calc R U . . .
C17 C 0.6579(3) 0.6221(2) 0.30382(13) 0.0609(6) Uani 1 1 d . . . . .
H17 H 0.576119 0.589086 0.273782 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1803(3) 0.15127(18) 0.36525(15) 0.0660(6) Uani 1 1 d . . . . .
H18 H 0.275231 0.133361 0.343670 0.079 Uiso 1 1 calc R U . . .
C19 C 0.1359(2) 0.26302(16) 0.37036(11) 0.0457(5) Uani 1 1 d . . . . .
C20 C -0.0059(2) 0.28739(19) 0.40193(12) 0.0538(5) Uani 1 1 d . . . . .
H20 H -0.038384 0.361759 0.406039 0.065 Uiso 1 1 calc R U . . .
C21 C -0.1006(3) 0.2014(2) 0.42768(14) 0.0687(7) Uani 1 1 d . . . . .
H21 H -0.196454 0.218510 0.448714 0.082 Uiso 1 1 calc R U . . .
C22 C -0.0535(3) 0.0920(2) 0.42222(15) 0.0752(7) Uani 1 1 d . U . . .
H22 H -0.117135 0.034741 0.439557 0.090 Uiso 1 1 calc R U . . .
C23 C 0.0880(4) 0.0666(2) 0.39112(16) 0.0775(8) Uani 1 1 d . U . . .
H23 H 0.120811 -0.007781 0.387673 0.093 Uiso 1 1 calc R U . . .
O1 O 0.28463(16) 0.32253(12) 0.26529(8) 0.0523(4) Uani 1 1 d . . . . .
O2 O 0.49666(17) 0.44444(14) 0.36015(9) 0.0658(5) Uani 1 1 d . . . . .
O3 O 0.65801(19) 0.43421(14) 0.46436(10) 0.0719(5) 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
C1 H1 0.9300 . ?
C1 C2 1.376(3) . ?
C1 C6 1.376(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 C4 1.397(3) . ?
C3 O1 1.378(2) . ?
C4 C5 1.390(3) . ?
C4 C7 1.443(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.314(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.495(3) . ?
C9 C10 1.518(3) . ?
C9 C19 1.531(3) . ?
C9 O1 1.446(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 O2 1.438(3) . ?
C11 C12 1.485(3) . ?
C11 O2 1.334(2) . ?
C11 O3 1.196(2) . ?
C12 C13 1.382(3) . ?
C12 C17 1.385(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C18 C23 1.367(3) . ?
C19 C20 1.377(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.365(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(4) . ?
C23 H23 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
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(2) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 O1 118.53(19) . . ?
O1 C3 C4 120.00(18) . . ?
C3 C4 C7 117.85(19) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 124.6(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C4 C7 H7 119.8 . . ?
C8 C7 C4 120.33(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.71(19) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 110.77(17) . . ?
C8 C9 C19 113.03(16) . . ?
C10 C9 C19 108.74(17) . . ?
O1 C9 C8 110.74(16) . . ?
O1 C9 C10 104.98(16) . . ?
O1 C9 C19 108.23(15) . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O2 C10 C9 107.61(17) . . ?
O2 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
O2 C11 C12 111.92(18) . . ?
O3 C11 C12 124.80(19) . . ?
O3 C11 O2 123.3(2) . . ?
C13 C12 C11 118.49(19) . . ?
C13 C12 C17 118.9(2) . . ?
C17 C12 C11 122.60(19) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 119.9 . . ?
C19 C18 H18 119.2 . . ?
C23 C18 H18 119.2 . . ?
C23 C18 C19 121.7(2) . . ?
C18 C19 C9 119.52(18) . . ?
C20 C19 C9 122.38(18) . . ?
C20 C19 C18 118.10(19) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 119.6(2) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C3 O1 C9 116.88(14) . . ?
C11 O2 C10 116.96(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 O1 -176.53(19) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C7 -177.33(18) . . . . ?
C2 C3 O1 C9 -153.58(17) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C7 C8 -12.7(3) . . . . ?
C4 C3 O1 C9 30.1(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C7 C8 C9 -3.0(3) . . . . ?
C5 C4 C7 C8 170.4(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C7 C4 C5 C6 177.3(2) . . . . ?
C7 C8 C9 C10 145.9(2) . . . . ?
C7 C8 C9 C19 -91.8(2) . . . . ?
C7 C8 C9 O1 29.8(3) . . . . ?
C8 C9 C10 O2 -52.7(2) . . . . ?
C8 C9 C19 C18 171.61(19) . . . . ?
C8 C9 C19 C20 -7.6(3) . . . . ?
C8 C9 O1 C3 -42.7(2) . . . . ?
C9 C10 O2 C11 162.98(18) . . . . ?
C9 C19 C20 C21 179.25(19) . . . . ?
C10 C9 C19 C18 -64.9(2) . . . . ?
C10 C9 C19 C20 115.8(2) . . . . ?
C10 C9 O1 C3 -162.31(15) . . . . ?
C11 C12 C13 C14 -177.7(2) . . . . ?
C11 C12 C17 C16 178.4(2) . . . . ?
C12 C11 O2 C10 -175.29(17) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C17 C12 C13 C14 0.6(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C9 C10 O2 -177.44(17) . . . . ?
C19 C9 O1 C3 81.69(19) . . . . ?
C19 C18 C23 C22 0.8(4) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C18 -0.5(4) . . . . ?
C23 C18 C19 C9 -179.8(2) . . . . ?
C23 C18 C19 C20 -0.6(3) . . . . ?
O1 C3 C4 C5 176.07(18) . . . . ?
O1 C3 C4 C7 -1.1(3) . . . . ?
O1 C9 C10 O2 66.9(2) . . . . ?
O1 C9 C19 C18 48.6(2) . . . . ?
O1 C9 C19 C20 -130.66(19) . . . . ?
O2 C11 C12 C13 174.31(18) . . . . ?
O2 C11 C12 C17 -4.0(3) . . . . ?
O3 C11 C12 C13 -4.5(3) . . . . ?
O3 C11 C12 C17 177.2(2) . . . . ?
O3 C11 O2 C10 3.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
