# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_mo_d8v21709_0m
_database_code_depnum_ccdc_archive 'CCDC 2202991'
loop_
_audit_author_name
_audit_author_address
'Jie Sun '
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 O4'
_chemical_formula_weight         386.42

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.2186(9)
_cell_length_b                   10.7453(13)
_cell_length_c                   12.2370(14)
_cell_angle_alpha                115.168(3)
_cell_angle_beta                 93.669(4)
_cell_angle_gamma                93.606(4)
_cell_volume                     971.20(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      4.992
_cell_measurement_theta_max      55.007

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22564
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3771
_reflns_number_gt                3428
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0425P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.053(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_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 0.09617(11) 0.42474(9) 0.63091(8) 0.0388(2) Uani 1 1 d . . . . .
O2 O 0.31412(11) 0.49846(9) 0.56441(7) 0.0345(2) Uani 1 1 d . . . . .
O3 O 0.28288(18) 0.83481(10) 0.90374(9) 0.0636(4) Uani 1 1 d . . . . .
O4 O 0.15422(11) 0.74522(9) 0.71735(8) 0.0407(2) Uani 1 1 d . . . . .
C1 C 0.32007(13) 0.09982(11) 0.53329(10) 0.0270(2) Uani 1 1 d . . . . .
H1 H 0.2713 0.0972 0.5998 0.032 Uiso 1 1 calc R U . . .
C2 C 0.25636(13) 0.00479(11) 0.41410(10) 0.0267(2) Uani 1 1 d . . . . .
C3 C 0.12535(14) -0.09808(12) 0.39052(11) 0.0329(3) Uani 1 1 d . . . . .
H3 H 0.0810 -0.1078 0.4558 0.039 Uiso 1 1 calc R U . . .
C4 C 0.06232(15) -0.18351(13) 0.27441(12) 0.0377(3) Uani 1 1 d . . . . .
H4 H -0.0250 -0.2509 0.2605 0.045 Uiso 1 1 calc R U . . .
C5 C 0.12752(16) -0.17113(13) 0.17525(11) 0.0370(3) Uani 1 1 d . . . . .
H5 H 0.0808 -0.2279 0.0958 0.044 Uiso 1 1 calc R U . . .
C6 C 0.25797(15) -0.07725(13) 0.19431(11) 0.0338(3) Uani 1 1 d . . . . .
H6 H 0.3029 -0.0718 0.1275 0.041 Uiso 1 1 calc R U . . .
C7 C 0.32717(14) 0.01274(11) 0.31396(10) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.46432(15) 0.10989(12) 0.33717(11) 0.0319(3) Uani 1 1 d . . . . .
H8 H 0.5137 0.1146 0.2717 0.038 Uiso 1 1 calc R U . . .
C9 C 0.52621(15) 0.19684(12) 0.45287(11) 0.0311(3) Uani 1 1 d . . . . .
H9 H 0.6196 0.2585 0.4661 0.037 Uiso 1 1 calc R U . . .
C10 C 0.45071(13) 0.19519(11) 0.55389(10) 0.0266(2) Uani 1 1 d . . . . .
C11 C 0.51512(14) 0.29840(11) 0.67740(10) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.6283 0.3260 0.6916 0.034 Uiso 1 1 calc R U . . .
C12 C 0.42722(13) 0.35429(11) 0.76834(10) 0.0261(2) Uani 1 1 d . . . . .
C13 C 0.33877(13) 0.41736(11) 0.85822(9) 0.0239(2) Uani 1 1 d . . . . .
C14 C 0.30326(13) 0.36205(11) 0.94794(10) 0.0252(2) Uani 1 1 d . . . . .
C15 C 0.35068(16) 0.23397(12) 0.93275(11) 0.0351(3) Uani 1 1 d . . . . .
H15 H 0.4057 0.1824 0.8653 0.042 Uiso 1 1 calc R U . . .
C16 C 0.31817(19) 0.18145(14) 1.01530(13) 0.0439(3) Uani 1 1 d . . . . .
H16 H 0.3513 0.0949 1.0036 0.053 Uiso 1 1 calc R U . . .
C17 C 0.23689(17) 0.25581(14) 1.11517(12) 0.0408(3) Uani 1 1 d . . . . .
H17 H 0.2145 0.2199 1.1711 0.049 Uiso 1 1 calc R U . . .
C18 C 0.18899(15) 0.38298(14) 1.13200(11) 0.0363(3) Uani 1 1 d . . . . .
H18 H 0.1340 0.4339 1.1997 0.044 Uiso 1 1 calc R U . . .
C19 C 0.22176(14) 0.43598(12) 1.04925(10) 0.0304(3) Uani 1 1 d . . . . .
H19 H 0.1887 0.5227 1.0615 0.036 Uiso 1 1 calc R U . . .
C20 C 0.26769(14) 0.54998(11) 0.87358(10) 0.0268(2) Uani 1 1 d . . . . .
H20A H 0.3123 0.6237 0.9524 0.032 Uiso 1 1 calc R U . . .
H20B H 0.1488 0.5373 0.8746 0.032 Uiso 1 1 calc R U . . .
C21 C 0.30261(14) 0.59608(11) 0.77457(10) 0.0262(2) Uani 1 1 d . . . . .
H21 H 0.4227 0.6034 0.7712 0.031 Uiso 1 1 calc R U . . .
C22 C 0.22384(14) 0.49497(11) 0.65007(10) 0.0272(3) Uani 1 1 d . . . . .
C23 C 0.24376(19) 0.41908(16) 0.44084(11) 0.0476(4) Uani 1 1 d . . . . .
H23A H 0.3207 0.4249 0.3859 0.071 Uiso 1 1 calc R U . . .
H23B H 0.1432 0.4556 0.4276 0.071 Uiso 1 1 calc R U . . .
H23C H 0.2200 0.3233 0.4259 0.071 Uiso 1 1 calc R U . . .
C24 C 0.24548(15) 0.73869(12) 0.80773(10) 0.0312(3) Uani 1 1 d . . . . .
C25 C 0.09944(18) 0.87873(14) 0.74003(16) 0.0494(4) Uani 1 1 d . . . . .
H25A H 0.0198 0.8689 0.6741 0.074 Uiso 1 1 calc R U . . .
H25B H 0.1924 0.9420 0.7454 0.074 Uiso 1 1 calc R U . . .
H25C H 0.0494 0.9147 0.8157 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
O1 C22 1.2017(14) . ?
O2 C22 1.3342(14) . ?
O2 C23 1.4414(15) . ?
O3 C24 1.1930(15) . ?
O4 C24 1.3255(15) . ?
O4 C25 1.4479(15) . ?
C1 C10 1.3688(16) . ?
C1 C2 1.4187(16) . ?
C1 H1 0.9400 . ?
C2 C3 1.4155(16) . ?
C2 C7 1.4218(16) . ?
C3 C4 1.3662(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.4102(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3614(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4221(16) . ?
C6 H6 0.9400 . ?
C7 C8 1.4142(17) . ?
C8 C9 1.3635(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.4245(16) . ?
C9 H9 0.9400 . ?
C10 C11 1.4807(15) . ?
C11 C12 1.3077(16) . ?
C11 H11 0.9400 . ?
C12 C13 1.3144(16) . ?
C13 C14 1.4894(15) . ?
C13 C20 1.5160(15) . ?
C14 C15 1.3927(16) . ?
C14 C19 1.3972(16) . ?
C15 C16 1.3823(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.3796(19) . ?
C17 H17 0.9400 . ?
C18 C19 1.3887(17) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.5273(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.5159(15) . ?
C21 C24 1.5229(15) . ?
C21 H21 0.9900 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?

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
C22 O2 C23 115.96(10) . . ?
C24 O4 C25 116.25(10) . . ?
C10 C1 C2 121.68(10) . . ?
C10 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 122.76(10) . . ?
C3 C2 C7 118.51(11) . . ?
C1 C2 C7 118.73(10) . . ?
C4 C3 C2 121.00(11) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.40(12) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.19(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.83(11) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C2 118.66(10) . . ?
C8 C7 C6 122.41(11) . . ?
C2 C7 C6 118.94(11) . . ?
C9 C8 C7 121.19(10) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.66(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C10 C9 118.94(10) . . ?
C1 C10 C11 122.43(10) . . ?
C9 C10 C11 118.63(10) . . ?
C12 C11 C10 125.24(10) . . ?
C12 C11 H11 117.4 . . ?
C10 C11 H11 117.4 . . ?
C11 C12 C13 176.35(12) . . ?
C12 C13 C14 121.93(10) . . ?
C12 C13 C20 120.67(10) . . ?
C14 C13 C20 117.40(9) . . ?
C15 C14 C19 117.97(11) . . ?
C15 C14 C13 120.55(10) . . ?
C19 C14 C13 121.48(10) . . ?
C16 C15 C14 121.08(12) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.29(12) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.57(12) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.21(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.88(11) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C13 C20 C21 114.19(9) . . ?
C13 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C13 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C24 110.20(9) . . ?
C22 C21 C20 112.89(9) . . ?
C24 C21 C20 109.59(9) . . ?
C22 C21 H21 108.0 . . ?
C24 C21 H21 108.0 . . ?
C20 C21 H21 108.0 . . ?
O1 C22 O2 124.81(11) . . ?
O1 C22 C21 124.99(10) . . ?
O2 C22 C21 110.16(9) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 O4 123.86(11) . . ?
O3 C24 C21 123.37(11) . . ?
O4 C24 C21 112.74(10) . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C10 C1 C2 C3 177.60(10) . . . . ?
C10 C1 C2 C7 -2.21(16) . . . . ?
C1 C2 C3 C4 176.88(11) . . . . ?
C7 C2 C3 C4 -3.30(17) . . . . ?
C2 C3 C4 C5 0.30(18) . . . . ?
C3 C4 C5 C6 2.45(19) . . . . ?
C4 C5 C6 C7 -2.09(18) . . . . ?
C3 C2 C7 C8 -176.27(10) . . . . ?
C1 C2 C7 C8 3.55(15) . . . . ?
C3 C2 C7 C6 3.59(16) . . . . ?
C1 C2 C7 C6 -176.58(10) . . . . ?
C5 C6 C7 C8 178.91(11) . . . . ?
C5 C6 C7 C2 -0.95(17) . . . . ?
C2 C7 C8 C9 -1.46(17) . . . . ?
C6 C7 C8 C9 178.68(11) . . . . ?
C7 C8 C9 C10 -2.06(18) . . . . ?
C2 C1 C10 C9 -1.26(16) . . . . ?
C2 C1 C10 C11 177.77(10) . . . . ?
C8 C9 C10 C1 3.44(17) . . . . ?
C8 C9 C10 C11 -175.63(10) . . . . ?
C1 C10 C11 C12 -32.42(17) . . . . ?
C9 C10 C11 C12 146.61(12) . . . . ?
C12 C13 C14 C15 -5.92(16) . . . . ?
C20 C13 C14 C15 173.65(10) . . . . ?
C12 C13 C14 C19 174.17(11) . . . . ?
C20 C13 C14 C19 -6.25(15) . . . . ?
C19 C14 C15 C16 0.01(18) . . . . ?
C13 C14 C15 C16 -179.89(11) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C17 C18 C19 C14 0.03(18) . . . . ?
C15 C14 C19 C18 -0.10(17) . . . . ?
C13 C14 C19 C18 179.80(10) . . . . ?
C12 C13 C20 C21 2.40(15) . . . . ?
C14 C13 C20 C21 -177.18(9) . . . . ?
C13 C20 C21 C22 64.10(12) . . . . ?
C13 C20 C21 C24 -172.66(9) . . . . ?
C23 O2 C22 O1 4.94(17) . . . . ?
C23 O2 C22 C21 -173.06(10) . . . . ?
C24 C21 C22 O1 -90.59(13) . . . . ?
C20 C21 C22 O1 32.31(15) . . . . ?
C24 C21 C22 O2 87.40(11) . . . . ?
C20 C21 C22 O2 -149.69(9) . . . . ?
C25 O4 C24 O3 0.13(19) . . . . ?
C25 O4 C24 C21 -177.95(10) . . . . ?
C22 C21 C24 O3 175.88(13) . . . . ?
C20 C21 C24 O3 51.06(17) . . . . ?
C22 C21 C24 O4 -6.03(14) . . . . ?
C20 C21 C24 O4 -130.84(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23B O1 0.97 2.64 3.5946(18) 169.1 2_566

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

