# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_tsy20241008_1_0ma
_database_code_depnum_ccdc_archive 'CCDC 2389698'
loop_
_audit_author_name
_audit_author_address
'Huan-Ming Huang'
;ShanghaiTech University
China
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_audit_creation_date             2024-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 O3'
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33
_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 0.0137 0.0067 '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 0.0389 0.0241 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.8872(3)
_cell_length_b                   8.5462(3)
_cell_length_c                   32.7304(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3045.37(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6521
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      56.97
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1123 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8453.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            22040
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.018
_diffrn_reflns_theta_min         2.349
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           1.14
_diffrn_source_power             0.07964039999999999
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2737
_reflns_number_total             3104
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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         0.310
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.112
_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)+(0.0440P)²+1.8131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C00B(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00E), C00D(H00F), C00E(H00G), C00F(H00H), C00G(H00I), C00H(H00J),
 C00I(H00K), C00J(H00L), C00K(H00M), C00L(H00N)
2.d Idealised Me refined as rotating group:
 C00M(H00O,H00P,H00Q)
;
_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
O001 O 0.41194(10) 0.09621(13) 0.34413(3) 0.0235(3) Uani 1 1 d . . . . .
O002 O 0.45579(13) 0.55896(16) 0.41183(4) 0.0383(3) Uani 1 1 d . . . . .
O003 O 0.33272(14) 0.39917(17) 0.44714(4) 0.0471(4) Uani 1 1 d . . . . .
C004 C 0.53064(15) 0.09196(19) 0.40797(5) 0.0236(4) Uani 1 1 d . . . . .
C005 C 0.48459(16) 0.3532(2) 0.34317(5) 0.0258(4) Uani 1 1 d . . . . .
H00A H 0.484740 0.462181 0.332886 0.031 Uiso 1 1 calc R U . . .
H00B H 0.568701 0.310342 0.345755 0.031 Uiso 1 1 calc R U . . .
C006 C 0.41537(14) 0.14598(19) 0.38667(5) 0.0226(3) Uani 1 1 d . . . . .
H006 H 0.341941 0.103704 0.401329 0.027 Uiso 1 1 calc R U . . .
C007 C 0.39989(15) 0.3235(2) 0.38035(5) 0.0244(4) Uani 1 1 d . . . . .
C008 C 0.39234(16) 0.4278(2) 0.41712(5) 0.0278(4) Uani 1 1 d . . . . .
C009 C 0.39155(15) 0.24407(19) 0.32251(5) 0.0232(4) Uani 1 1 d . . . . .
C00A C 0.38115(15) 0.2215(2) 0.27734(5) 0.0246(4) Uani 1 1 d . . . . .
C00B C 0.29129(16) 0.3213(2) 0.34917(5) 0.0292(4) Uani 1 1 d . . . . .
H00C H 0.221740 0.252351 0.356615 0.035 Uiso 1 1 calc R U . . .
H00D H 0.263408 0.425505 0.339747 0.035 Uiso 1 1 calc R U . . .
C00C C 0.45191(17) 0.2770(2) 0.20907(5) 0.0340(4) Uani 1 1 d . . . . .
H00E H 0.509761 0.325149 0.191349 0.041 Uiso 1 1 calc R U . . .
C00D C 0.54141(17) 0.1121(2) 0.45009(5) 0.0314(4) Uani 1 1 d . . . . .
H00F H 0.476585 0.160620 0.464834 0.038 Uiso 1 1 calc R U . . .
C00E C 0.62531(16) 0.0181(2) 0.38735(5) 0.0343(4) Uani 1 1 d . . . . .
H00G H 0.619731 0.003170 0.358651 0.041 Uiso 1 1 calc R U . . .
C00F C 0.35519(18) 0.1925(2) 0.19299(5) 0.0336(4) Uani 1 1 d . . . . .
H00H H 0.345979 0.183158 0.164236 0.040 Uiso 1 1 calc R U . . .
C00G C 0.46475(16) 0.2917(2) 0.25123(5) 0.0305(4) Uani 1 1 d . . . . .
H00I H 0.531259 0.350240 0.262148 0.037 Uiso 1 1 calc R U . . .
C00H C 0.64530(18) 0.0625(2) 0.47069(5) 0.0372(4) Uani 1 1 d . . . . .
H00J H 0.652331 0.079744 0.499266 0.045 Uiso 1 1 calc R U . . .
C00I C 0.28411(17) 0.1363(2) 0.26090(5) 0.0338(4) Uani 1 1 d . . . . .
H00K H 0.226006 0.088093 0.278512 0.041 Uiso 1 1 calc R U . . .
C00J C 0.27187(19) 0.1216(2) 0.21891(6) 0.0382(5) Uani 1 1 d . . . . .
H00L H 0.205825 0.062507 0.207895 0.046 Uiso 1 1 calc R U . . .
C00K C 0.73864(18) -0.0120(3) 0.44993(6) 0.0401(5) Uani 1 1 d . . . . .
H00M H 0.809399 -0.047511 0.464159 0.048 Uiso 1 1 calc R U . . .
C00L C 0.72851(18) -0.0346(3) 0.40829(6) 0.0462(6) Uani 1 1 d . . . . .
H00N H 0.792388 -0.086359 0.393867 0.055 Uiso 1 1 calc R U . . .
C00M C 0.4500(2) 0.6715(3) 0.44523(7) 0.0492(6) Uani 1 1 d . . . . .
H00O H 0.503086 0.760980 0.439002 0.074 Uiso 1 1 calc R U . . .
H00P H 0.477748 0.621593 0.470546 0.074 Uiso 1 1 calc R U . . .
H00Q H 0.365146 0.707697 0.448584 0.074 Uiso 1 1 calc R U . . .


_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
O001 C006 1.4564(18) . ?
O001 C009 1.4651(19) . ?
O002 C008 1.328(2) . ?
O002 C00M 1.457(2) . ?
O003 C008 1.203(2) . ?
C004 C006 1.508(2) . ?
C004 C00D 1.394(2) . ?
C004 C00E 1.384(2) . ?
C005 H00A 0.9900 . ?
C005 H00B 0.9900 . ?
C005 C007 1.548(2) . ?
C005 C009 1.534(2) . ?
C006 H006 1.0000 . ?
C006 C007 1.540(2) . ?
C007 C008 1.500(2) . ?
C007 C00B 1.562(2) . ?
C009 C00A 1.495(2) . ?
C009 C00B 1.546(2) . ?
C00A C00G 1.385(2) . ?
C00A C00I 1.391(2) . ?
C00B H00C 0.9900 . ?
C00B H00D 0.9900 . ?
C00C H00E 0.9500 . ?
C00C C00F 1.381(3) . ?
C00C C00G 1.393(2) . ?
C00D H00F 0.9500 . ?
C00D C00H 1.384(3) . ?
C00E H00G 0.9500 . ?
C00E C00L 1.391(3) . ?
C00F H00H 0.9500 . ?
C00F C00J 1.382(3) . ?
C00G H00I 0.9500 . ?
C00H H00J 0.9500 . ?
C00H C00K 1.378(3) . ?
C00I H00K 0.9500 . ?
C00I C00J 1.387(2) . ?
C00J H00L 0.9500 . ?
C00K H00M 0.9500 . ?
C00K C00L 1.381(3) . ?
C00L H00N 0.9500 . ?
C00M H00O 0.9800 . ?
C00M H00P 0.9800 . ?
C00M H00Q 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
C006 O001 C009 102.34(11) . . ?
C008 O002 C00M 115.89(15) . . ?
C00D C004 C006 119.29(15) . . ?
C00E C004 C006 122.26(14) . . ?
C00E C004 C00D 118.41(16) . . ?
H00A C005 H00B 112.1 . . ?
C007 C005 H00A 115.0 . . ?
C007 C005 H00B 115.0 . . ?
C009 C005 H00A 115.0 . . ?
C009 C005 H00B 115.0 . . ?
C009 C005 C007 81.56(12) . . ?
O001 C006 C004 111.96(13) . . ?
O001 C006 H006 109.4 . . ?
O001 C006 C007 99.01(12) . . ?
C004 C006 H006 109.4 . . ?
C004 C006 C007 117.04(13) . . ?
C007 C006 H006 109.4 . . ?
C005 C007 C00B 86.51(12) . . ?
C006 C007 C005 101.67(13) . . ?
C006 C007 C00B 99.14(13) . . ?
C008 C007 C005 124.44(15) . . ?
C008 C007 C006 118.94(14) . . ?
C008 C007 C00B 119.32(14) . . ?
O002 C008 C007 111.63(14) . . ?
O003 C008 O002 124.00(16) . . ?
O003 C008 C007 124.32(17) . . ?
O001 C009 C005 102.22(12) . . ?
O001 C009 C00A 112.18(13) . . ?
O001 C009 C00B 101.70(12) . . ?
C005 C009 C00B 87.58(12) . . ?
C00A C009 C005 124.36(14) . . ?
C00A C009 C00B 124.04(14) . . ?
C00G C00A C009 120.30(15) . . ?
C00G C00A C00I 119.13(15) . . ?
C00I C00A C009 120.50(15) . . ?
C007 C00B H00C 115.1 . . ?
C007 C00B H00D 115.1 . . ?
C009 C00B C007 80.75(12) . . ?
C009 C00B H00C 115.1 . . ?
C009 C00B H00D 115.1 . . ?
H00C C00B H00D 112.2 . . ?
C00F C00C H00E 120.0 . . ?
C00F C00C C00G 120.08(17) . . ?
C00G C00C H00E 120.0 . . ?
C004 C00D H00F 119.6 . . ?
C00H C00D C004 120.83(16) . . ?
C00H C00D H00F 119.6 . . ?
C004 C00E H00G 119.7 . . ?
C004 C00E C00L 120.58(16) . . ?
C00L C00E H00G 119.7 . . ?
C00C C00F H00H 120.1 . . ?
C00C C00F C00J 119.73(16) . . ?
C00J C00F H00H 120.1 . . ?
C00A C00G C00C 120.43(17) . . ?
C00A C00G H00I 119.8 . . ?
C00C C00G H00I 119.8 . . ?
C00D C00H H00J 119.9 . . ?
C00K C00H C00D 120.29(16) . . ?
C00K C00H H00J 119.9 . . ?
C00A C00I H00K 119.9 . . ?
C00J C00I C00A 120.25(17) . . ?
C00J C00I H00K 119.9 . . ?
C00F C00J C00I 120.38(18) . . ?
C00F C00J H00L 119.8 . . ?
C00I C00J H00L 119.8 . . ?
C00H C00K H00M 120.3 . . ?
C00H C00K C00L 119.49(17) . . ?
C00L C00K H00M 120.3 . . ?
C00E C00L H00N 119.8 . . ?
C00K C00L C00E 120.37(18) . . ?
C00K C00L H00N 119.8 . . ?
O002 C00M H00O 109.5 . . ?
O002 C00M H00P 109.5 . . ?
O002 C00M H00Q 109.5 . . ?
H00O C00M H00P 109.5 . . ?
H00O C00M H00Q 109.5 . . ?
H00P C00M H00Q 109.5 . . ?

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
O001 C006 C007 C005 -41.90(14) . . . . ?
O001 C006 C007 C008 177.38(13) . . . . ?
O001 C006 C007 C00B 46.40(13) . . . . ?
O001 C009 C00A C00G -118.51(17) . . . . ?
O001 C009 C00A C00I 64.7(2) . . . . ?
O001 C009 C00B C007 66.37(12) . . . . ?
C004 C006 C007 C005 78.50(16) . . . . ?
C004 C006 C007 C008 -62.2(2) . . . . ?
C004 C006 C007 C00B 166.80(13) . . . . ?
C004 C00D C00H C00K -1.8(3) . . . . ?
C004 C00E C00L C00K -0.8(3) . . . . ?
C005 C007 C008 O002 7.7(2) . . . . ?
C005 C007 C008 O003 -174.80(17) . . . . ?
C005 C007 C00B C009 35.29(11) . . . . ?
C005 C009 C00A C00G 5.2(2) . . . . ?
C005 C009 C00A C00I -171.54(16) . . . . ?
C005 C009 C00B C007 -35.61(12) . . . . ?
C006 O001 C009 C005 46.17(14) . . . . ?
C006 O001 C009 C00A -178.44(13) . . . . ?
C006 O001 C009 C00B -43.87(14) . . . . ?
C006 C004 C00D C00H 179.31(17) . . . . ?
C006 C004 C00E C00L -177.92(19) . . . . ?
C006 C007 C008 O002 138.95(15) . . . . ?
C006 C007 C008 O003 -43.5(2) . . . . ?
C006 C007 C00B C009 -65.98(13) . . . . ?
C007 C005 C009 O001 -65.55(12) . . . . ?
C007 C005 C009 C00A 166.43(16) . . . . ?
C007 C005 C009 C00B 35.90(11) . . . . ?
C008 C007 C00B C009 163.29(16) . . . . ?
C009 O001 C006 C004 -126.07(13) . . . . ?
C009 O001 C006 C007 -2.00(14) . . . . ?
C009 C005 C007 C006 63.13(13) . . . . ?
C009 C005 C007 C008 -159.08(16) . . . . ?
C009 C005 C007 C00B -35.50(12) . . . . ?
C009 C00A C00G C00C -176.94(16) . . . . ?
C009 C00A C00I C00J 177.12(17) . . . . ?
C00A C009 C00B C007 -166.39(16) . . . . ?
C00A C00I C00J C00F -0.6(3) . . . . ?
C00B C007 C008 O002 -99.80(18) . . . . ?
C00B C007 C008 O003 77.7(2) . . . . ?
C00B C009 C00A C00G 118.83(19) . . . . ?
C00B C009 C00A C00I -58.0(2) . . . . ?
C00C C00F C00J C00I 0.7(3) . . . . ?
C00D C004 C006 O001 -171.81(15) . . . . ?
C00D C004 C006 C007 74.9(2) . . . . ?
C00D C004 C00E C00L 0.0(3) . . . . ?
C00D C00H C00K C00L 1.0(3) . . . . ?
C00E C004 C006 O001 6.1(2) . . . . ?
C00E C004 C006 C007 -107.20(19) . . . . ?
C00E C004 C00D C00H 1.3(3) . . . . ?
C00F C00C C00G C00A 0.2(3) . . . . ?
C00G C00A C00I C00J 0.3(3) . . . . ?
C00G C00C C00F C00J -0.5(3) . . . . ?
C00H C00K C00L C00E 0.4(4) . . . . ?
C00I C00A C00G C00C -0.1(3) . . . . ?
C00M O002 C008 O003 -0.1(3) . . . . ?
C00M O002 C008 C007 177.47(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
