# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tqf022
_database_code_depnum_ccdc_archive 'CCDC 2331720'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2024-02-08 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O4'
_chemical_formula_sum            'C20 H18 O4'
_chemical_formula_weight         322.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.34150(10)
_cell_length_b                   8.4205(2)
_cell_length_c                   30.8465(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1647.16(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      68.27

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.228
_exptl_absorpt_coefficient_mu    0.735
_shelx_estimated_absorpt_T_min   0.697
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7301
_exptl_absorpt_correction_T_max  0.9096
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12771
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3013
_reflns_number_gt                2993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0310P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0157(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_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
O1 O 0.5106(2) 0.40457(14) 0.67201(4) 0.0309(3) Uani 1 1 d . . . . .
O2 O 0.8559(2) 0.35592(15) 0.66184(5) 0.0410(3) Uani 1 1 d . . . . .
O3 O 0.37173(19) 0.72251(15) 0.66157(4) 0.0314(3) Uani 1 1 d . . . . .
O4 O 0.63853(17) 0.87671(12) 0.64009(3) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.4802(3) 0.2360(2) 0.73531(6) 0.0378(4) Uani 1 1 d . . . . .
H1A H 0.453409 0.127113 0.745075 0.057 Uiso 1 1 calc R U . . .
H1B H 0.372561 0.306961 0.747312 0.057 Uiso 1 1 calc R U . . .
H1C H 0.619887 0.269943 0.745267 0.057 Uiso 1 1 calc R U . . .
C2 C 0.4723(3) 0.2421(2) 0.68670(6) 0.0344(4) Uani 1 1 d . . . . .
H2A H 0.580625 0.170322 0.674434 0.041 Uiso 1 1 calc R U . . .
H2B H 0.332353 0.205971 0.676473 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7063(3) 0.44338(19) 0.66153(5) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.5534(2) 0.73462(19) 0.65187(5) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.7234(2) 0.61369(18) 0.64921(5) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.8955(2) 0.68299(17) 0.63365(5) 0.0200(3) Uani 1 1 d . . . . .
H6 H 1.025824 0.630672 0.628455 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8544(2) 0.85618(18) 0.62545(5) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.9990(3) 0.96621(17) 0.65193(5) 0.0228(3) Uani 1 1 d . . . . .
H8A H 1.144269 0.958156 0.640386 0.027 Uiso 1 1 calc R U . . .
H8B H 0.951500 1.077266 0.647979 0.027 Uiso 1 1 calc R U . . .
C9 C 1.0030(3) 0.9292(2) 0.69943(5) 0.0266(3) Uani 1 1 d . . . . .
H9 H 1.028053 0.822292 0.707797 0.032 Uiso 1 1 calc R U . . .
C10 C 0.9740(3) 1.0347(2) 0.73037(6) 0.0348(4) Uani 1 1 d . . . . .
H10A H 0.948532 1.142684 0.723164 0.052 Uiso 1 1 calc R U . . .
H10B H 0.978633 1.002797 0.759892 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8647(3) 0.89700(18) 0.57726(5) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.7058(3) 0.97995(18) 0.55750(5) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.585012 1.009691 0.573812 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7187(3) 1.02230(18) 0.51290(5) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.5567(3) 1.1093(2) 0.49213(6) 0.0296(4) Uani 1 1 d . . . . .
H14 H 0.435991 1.141214 0.508162 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5724(3) 1.1478(2) 0.44903(6) 0.0355(4) Uani 1 1 d . . . . .
H15 H 0.462381 1.205686 0.435351 0.043 Uiso 1 1 calc R U . . .
C16 C 0.7506(3) 1.1020(2) 0.42509(6) 0.0372(4) Uani 1 1 d . . . . .
H16 H 0.759827 1.128636 0.395225 0.045 Uiso 1 1 calc R U . . .
C17 C 0.9112(3) 1.0194(2) 0.44435(6) 0.0334(4) Uani 1 1 d . . . . .
H17 H 1.031186 0.989997 0.427762 0.040 Uiso 1 1 calc R U . . .
C18 C 0.9001(3) 0.97711(19) 0.48897(5) 0.0256(3) Uani 1 1 d . . . . .
C19 C 1.0618(3) 0.8911(2) 0.51011(6) 0.0290(4) Uani 1 1 d . . . . .
H19 H 1.183128 0.859605 0.494226 0.035 Uiso 1 1 calc R U . . .
C20 C 1.0461(3) 0.85272(19) 0.55311(6) 0.0268(4) Uani 1 1 d . . . . .
H20 H 1.157076 0.796135 0.566862 0.032 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
O1 C3 1.324(2) . ?
O1 C2 1.461(2) . ?
O2 C3 1.201(2) . ?
O3 C4 1.195(2) . ?
O4 C4 1.3620(19) . ?
O4 C7 1.4521(18) . ?
C1 C2 1.501(3) . ?
C3 C5 1.488(2) . ?
C4 C5 1.485(2) . ?
C5 C6 1.327(2) . ?
C6 C7 1.503(2) . ?
C7 C11 1.527(2) . ?
C7 C8 1.538(2) . ?
C8 C9 1.498(2) . ?
C9 C10 1.317(3) . ?
C11 C12 1.369(2) . ?
C11 C20 1.420(2) . ?
C12 C13 1.423(2) . ?
C13 C14 1.415(2) . ?
C13 C18 1.419(2) . ?
C14 C15 1.372(3) . ?
C15 C16 1.404(3) . ?
C16 C17 1.369(3) . ?
C17 C18 1.423(2) . ?
C18 C19 1.414(3) . ?
C19 C20 1.369(2) . ?

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
C3 O1 C2 117.56(14) . . ?
C4 O4 C7 110.62(11) . . ?
O1 C2 C1 109.64(15) . . ?
O2 C3 O1 125.96(15) . . ?
O2 C3 C5 122.40(15) . . ?
O1 C3 C5 111.63(14) . . ?
O3 C4 O4 121.61(14) . . ?
O3 C4 C5 130.94(15) . . ?
O4 C4 C5 107.44(12) . . ?
C6 C5 C4 108.39(13) . . ?
C6 C5 C3 125.17(14) . . ?
C4 C5 C3 126.44(14) . . ?
C5 C6 C7 110.17(13) . . ?
O4 C7 C6 103.09(12) . . ?
O4 C7 C11 108.44(12) . . ?
C6 C7 C11 112.02(12) . . ?
O4 C7 C8 108.96(12) . . ?
C6 C7 C8 113.06(12) . . ?
C11 C7 C8 110.86(12) . . ?
C9 C8 C7 113.84(13) . . ?
C10 C9 C8 124.49(16) . . ?
C12 C11 C20 119.77(14) . . ?
C12 C11 C7 121.11(14) . . ?
C20 C11 C7 119.09(14) . . ?
C11 C12 C13 121.04(14) . . ?
C14 C13 C18 119.47(15) . . ?
C14 C13 C12 121.70(16) . . ?
C18 C13 C12 118.83(15) . . ?
C15 C14 C13 120.55(17) . . ?
C14 C15 C16 120.21(17) . . ?
C17 C16 C15 120.67(16) . . ?
C16 C17 C18 120.68(17) . . ?
C19 C18 C13 119.02(15) . . ?
C19 C18 C17 122.56(16) . . ?
C13 C18 C17 118.41(16) . . ?
C20 C19 C18 120.99(15) . . ?
C19 C20 C11 120.34(15) . . ?

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
C3 O1 C2 C1 94.50(18) . . . . ?
C2 O1 C3 O2 2.1(2) . . . . ?
C2 O1 C3 C5 -177.32(13) . . . . ?
C7 O4 C4 O3 -173.82(15) . . . . ?
C7 O4 C4 C5 5.48(15) . . . . ?
O3 C4 C5 C6 175.21(17) . . . . ?
O4 C4 C5 C6 -4.00(16) . . . . ?
O3 C4 C5 C3 -4.5(3) . . . . ?
O4 C4 C5 C3 176.27(13) . . . . ?
O2 C3 C5 C6 6.6(2) . . . . ?
O1 C3 C5 C6 -173.87(15) . . . . ?
O2 C3 C5 C4 -173.67(16) . . . . ?
O1 C3 C5 C4 5.8(2) . . . . ?
C4 C5 C6 C7 0.96(16) . . . . ?
C3 C5 C6 C7 -179.31(14) . . . . ?
C4 O4 C7 C6 -4.78(14) . . . . ?
C4 O4 C7 C11 114.12(13) . . . . ?
C4 O4 C7 C8 -125.12(13) . . . . ?
C5 C6 C7 O4 2.18(16) . . . . ?
C5 C6 C7 C11 -114.20(15) . . . . ?
C5 C6 C7 C8 119.68(14) . . . . ?
O4 C7 C8 C9 62.83(16) . . . . ?
C6 C7 C8 C9 -51.17(18) . . . . ?
C11 C7 C8 C9 -177.91(13) . . . . ?
C7 C8 C9 C10 -129.49(19) . . . . ?
O4 C7 C11 C12 16.29(19) . . . . ?
C6 C7 C11 C12 129.40(15) . . . . ?
C8 C7 C11 C12 -103.29(17) . . . . ?
O4 C7 C11 C20 -165.97(13) . . . . ?
C6 C7 C11 C20 -52.87(19) . . . . ?
C8 C7 C11 C20 74.45(17) . . . . ?
C20 C11 C12 C13 0.3(2) . . . . ?
C7 C11 C12 C13 177.98(14) . . . . ?
C11 C12 C13 C14 -179.40(15) . . . . ?
C11 C12 C13 C18 0.0(2) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C12 C13 C14 C15 -179.63(17) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C14 C13 C18 C19 179.58(15) . . . . ?
C12 C13 C18 C19 0.2(2) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C12 C13 C18 C17 179.73(15) . . . . ?
C16 C17 C18 C19 179.67(17) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C13 C18 C19 C20 -0.6(3) . . . . ?
C17 C18 C19 C20 179.89(17) . . . . ?
C18 C19 C20 C11 0.8(3) . . . . ?
C12 C11 C20 C19 -0.7(2) . . . . ?
C7 C11 C20 C19 -178.42(15) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: IPA'
