# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1964780'
loop_
_audit_author_name
_audit_author_address
'Rajesh Kumar'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 O6'
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.9046(9)
_cell_length_b                   4.7807(2)
_cell_length_c                   17.8266(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.293(2)
_cell_angle_gamma                90.00
_cell_volume                     1861.55(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37246
_diffrn_reflns_av_R_equivalents  0.1663
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.57
_reflns_number_total             4270
_reflns_number_gt                3152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0537P)²+0.0730P] 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     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4270
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.53708(4) -0.2642(2) 0.59737(5) 0.0287(3) Uani 1 1 d . . .
O4 O 0.93404(4) 1.21056(19) 0.38738(5) 0.0187(2) Uani 1 1 d . . .
O3 O 0.92911(4) 1.1501(2) 0.51251(5) 0.0213(2) Uani 1 1 d . . .
O1 O 0.83338(4) 0.7366(2) 0.73457(5) 0.0282(3) Uani 1 1 d . . .
O5 O 0.59230(4) -0.0082(2) 0.68341(5) 0.0271(3) Uani 1 1 d . . .
O2 O 0.72034(4) 0.1556(2) 0.30058(5) 0.0224(2) Uani 1 1 d . . .
C20 C 0.45359(6) -0.5609(3) 0.61892(9) 0.0308(4) Uani 1 1 d . . .
H20A H 0.4281 -0.6376 0.6569 0.046 Uiso 1 1 calc R . .
H20B H 0.4738 -0.7143 0.5940 0.046 Uiso 1 1 calc R . .
H20C H 0.4278 -0.4554 0.5815 0.046 Uiso 1 1 calc R . .
C19 C 0.50112(6) -0.3702(3) 0.65623(8) 0.0274(3) Uani 1 1 d . . .
H19A H 0.4813 -0.2141 0.6817 0.033 Uiso 1 1 calc R . .
H19B H 0.5275 -0.4741 0.6941 0.033 Uiso 1 1 calc R . .
C18 C 0.58243(5) -0.0864(3) 0.61961(7) 0.0188(3) Uani 1 1 d . . .
C17 C 0.61708(6) -0.0050(3) 0.55494(7) 0.0262(3) Uani 1 1 d . . .
H17A H 0.6032 -0.0657 0.5059 0.031 Uiso 1 1 calc R . .
C16 C 0.66688(5) 0.1503(3) 0.56403(7) 0.0173(3) Uani 1 1 d . . .
H16A H 0.6795 0.2041 0.6141 0.021 Uiso 1 1 calc R . .
C6 C 0.70512(5) 0.2492(3) 0.50451(7) 0.0155(3) Uani 1 1 d . . .
C1 C 0.75231(5) 0.4436(3) 0.52167(7) 0.0143(3) Uani 1 1 d . . .
C2 C 0.78695(5) 0.5371(3) 0.46224(7) 0.0147(3) Uani 1 1 d . . .
C11 C 0.83657(5) 0.7416(3) 0.47723(7) 0.0160(3) Uani 1 1 d . . .
H11A H 0.8511 0.7697 0.5282 0.019 Uiso 1 1 calc R . .
C12 C 0.86290(5) 0.8907(3) 0.42543(7) 0.0175(3) Uani 1 1 d . . .
H12A H 0.8503 0.8669 0.3737 0.021 Uiso 1 1 calc R . .
C13 C 0.91162(5) 1.0929(3) 0.44842(7) 0.0156(3) Uani 1 1 d . . .
C14 C 0.98340(5) 1.4116(3) 0.40310(7) 0.0180(3) Uani 1 1 d . . .
H14A H 1.0213 1.3143 0.4224 0.022 Uiso 1 1 calc R . .
H14B H 0.9720 1.5484 0.4413 0.022 Uiso 1 1 calc R . .
C15 C 0.99336(6) 1.5576(3) 0.33055(8) 0.0251(3) Uani 1 1 d . . .
H15A H 1.0264 1.6950 0.3390 0.038 Uiso 1 1 calc R . .
H15B H 0.9556 1.6531 0.3120 0.038 Uiso 1 1 calc R . .
H15C H 1.0046 1.4200 0.2932 0.038 Uiso 1 1 calc R . .
C7 C 0.76710(5) 0.5510(3) 0.60065(6) 0.0159(3) Uani 1 1 d . . .
H7A H 0.7290 0.5592 0.6271 0.019 Uiso 1 1 calc R . .
H7B H 0.7835 0.7435 0.5982 0.019 Uiso 1 1 calc R . .
C8 C 0.81366(6) 0.3672(3) 0.64544(7) 0.0209(3) Uani 1 1 d . . .
H8A H 0.7936 0.1886 0.6574 0.025 Uiso 1 1 calc R . .
H8B H 0.8474 0.3230 0.6134 0.025 Uiso 1 1 calc R . .
C9 C 0.84019(6) 0.4949(3) 0.71688(7) 0.0238(3) Uani 1 1 d . . .
H9A H 0.8641 0.3786 0.7508 0.029 Uiso 1 1 calc R . .
C5 C 0.69332(5) 0.1476(3) 0.43108(7) 0.0164(3) Uani 1 1 d . . .
H5A H 0.6618 0.0138 0.4205 0.020 Uiso 1 1 calc R . .
C4 C 0.72773(5) 0.2424(3) 0.37377(7) 0.0163(3) Uani 1 1 d . . .
C10 C 0.67229(6) -0.0385(3) 0.28165(7) 0.0251(3) Uani 1 1 d . . .
H10A H 0.6717 -0.0845 0.2280 0.038 Uiso 1 1 calc R . .
H10B H 0.6330 0.0447 0.2924 0.038 Uiso 1 1 calc R . .
H10C H 0.6792 -0.2093 0.3115 0.038 Uiso 1 1 calc R . .
C3 C 0.77396(5) 0.4368(3) 0.38959(7) 0.0165(3) Uani 1 1 d . . .
H3A H 0.7971 0.5024 0.3501 0.020 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
O6 C18 1.3445(16) . ?
O6 C19 1.4498(14) . ?
O4 C13 1.3497(13) . ?
O4 C14 1.4580(14) . ?
O3 C13 1.2090(14) . ?
O1 C9 1.2100(17) . ?
O5 C18 1.2012(15) . ?
O2 C4 1.3671(14) . ?
O2 C10 1.4249(15) . ?
C20 C19 1.501(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C18 C17 1.4791(15) . ?
C17 C16 1.3193(17) . ?
C17 H17A 0.9500 . ?
C16 C6 1.4780(14) . ?
C16 H16A 0.9500 . ?
C6 C5 1.4021(17) . ?
C6 C1 1.4064(17) . ?
C1 C2 1.4208(14) . ?
C1 C7 1.5110(16) . ?
C2 C3 1.3904(17) . ?
C2 C11 1.4713(17) . ?
C11 C12 1.3315(16) . ?
C11 H11A 0.9500 . ?
C12 C13 1.4749(17) . ?
C12 H12A 0.9500 . ?
C14 C15 1.4998(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 C8 1.5259(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4905(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9500 . ?
C5 C4 1.3900(15) . ?
C5 H5A 0.9500 . ?
C4 C3 1.3877(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 H3A 0.9500 . ?

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
C18 O6 C19 115.91(10) . . ?
C13 O4 C14 115.42(10) . . ?
C4 O2 C10 117.15(9) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C19 C20 106.74(11) . . ?
O6 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
O6 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O5 C18 O6 123.54(11) . . ?
O5 C18 C17 126.13(12) . . ?
O6 C18 C17 110.33(11) . . ?
C16 C17 C18 121.34(12) . . ?
C16 C17 H17A 119.3 . . ?
C18 C17 H17A 119.3 . . ?
C17 C16 C6 126.85(12) . . ?
C17 C16 H16A 116.6 . . ?
C6 C16 H16A 116.6 . . ?
C5 C6 C1 120.87(10) . . ?
C5 C6 C16 118.99(11) . . ?
C1 C6 C16 120.15(11) . . ?
C6 C1 C2 118.08(11) . . ?
C6 C1 C7 122.01(10) . . ?
C2 C1 C7 119.91(11) . . ?
C3 C2 C1 120.16(11) . . ?
C3 C2 C11 119.69(10) . . ?
C1 C2 C11 120.15(11) . . ?
C12 C11 C2 125.60(12) . . ?
C12 C11 H11A 117.2 . . ?
C2 C11 H11A 117.2 . . ?
C11 C12 C13 120.00(12) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
O3 C13 O4 123.98(12) . . ?
O3 C13 C12 125.62(11) . . ?
O4 C13 C12 110.40(10) . . ?
O4 C14 C15 107.14(10) . . ?
O4 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O4 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C7 C8 112.34(10) . . ?
C1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 114.42(11) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O1 C9 C8 124.49(13) . . ?
O1 C9 H9A 117.8 . . ?
C8 C9 H9A 117.8 . . ?
C4 C5 C6 120.07(12) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
O2 C4 C3 115.44(10) . . ?
O2 C4 C5 124.78(11) . . ?
C3 C4 C5 119.77(11) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 C2 121.04(10) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?

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
C18 O6 C19 C20 179.70(12) . . . . ?
C19 O6 C18 O5 -2.6(2) . . . . ?
C19 O6 C18 C17 177.40(12) . . . . ?
O5 C18 C17 C16 5.7(2) . . . . ?
O6 C18 C17 C16 -174.39(13) . . . . ?
C18 C17 C16 C6 -179.11(12) . . . . ?
C17 C16 C6 C5 -8.0(2) . . . . ?
C17 C16 C6 C1 171.65(14) . . . . ?
C5 C6 C1 C2 1.00(19) . . . . ?
C16 C6 C1 C2 -178.64(11) . . . . ?
C5 C6 C1 C7 -178.40(11) . . . . ?
C16 C6 C1 C7 1.96(18) . . . . ?
C6 C1 C2 C3 -0.08(18) . . . . ?
C7 C1 C2 C3 179.34(11) . . . . ?
C6 C1 C2 C11 179.64(11) . . . . ?
C7 C1 C2 C11 -0.94(18) . . . . ?
C3 C2 C11 C12 15.5(2) . . . . ?
C1 C2 C11 C12 -164.18(13) . . . . ?
C2 C11 C12 C13 178.92(11) . . . . ?
C14 O4 C13 O3 1.73(18) . . . . ?
C14 O4 C13 C12 -179.04(10) . . . . ?
C11 C12 C13 O3 -3.9(2) . . . . ?
C11 C12 C13 O4 176.94(11) . . . . ?
C13 O4 C14 C15 -169.21(10) . . . . ?
C6 C1 C7 C8 88.78(13) . . . . ?
C2 C1 C7 C8 -90.61(14) . . . . ?
C1 C7 C8 C9 167.12(10) . . . . ?
C7 C8 C9 O1 -10.22(19) . . . . ?
C1 C6 C5 C4 -1.13(19) . . . . ?
C16 C6 C5 C4 178.51(12) . . . . ?
C10 O2 C4 C3 -178.41(12) . . . . ?
C10 O2 C4 C5 2.42(19) . . . . ?
C6 C5 C4 O2 179.46(12) . . . . ?
C6 C5 C4 C3 0.32(19) . . . . ?
O2 C4 C3 C2 -178.61(11) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C1 C2 C3 C4 -0.72(19) . . . . ?
C11 C2 C3 C4 179.56(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.065
