# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2258703'
loop_
_audit_author_name
_audit_author_address
'Jun Liu'
;RCEES
China
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 O6'
_chemical_formula_weight         320.33

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      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                   7.1304(2)
_cell_length_b                   10.9898(3)
_cell_length_c                   20.5390(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1609.47(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    12122
_cell_measurement_theta_min      1.9760
_cell_measurement_theta_max      30.7420

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.93218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.946
_oxdiff_exptl_absorpt_empirical_full_max 1.073
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       ?
_diffrn_reflns_number            19468
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         30.671
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4382
_reflns_number_gt                3868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.825
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0606P)²+0.0345P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4382
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 1.04762(19) 0.29864(14) 0.70014(8) 0.0465(4) Uani 1 1 d . . . . .
O2 O 0.74994(16) 0.24097(11) 0.71274(5) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.40739(16) 0.46912(12) 0.66581(6) 0.0301(3) Uani 1 1 d . . . . .
O4 O 0.71449(17) 0.56868(10) 0.60030(6) 0.0277(3) Uani 1 1 d . . . . .
O5 O 0.63356(16) 0.23819(10) 0.58140(5) 0.0248(2) Uani 1 1 d . . . . .
O6 O 0.3900(2) 0.13906(12) 0.54559(8) 0.0482(4) Uani 1 1 d . . . . .
C1 C 0.9360(2) 0.22658(17) 0.72053(8) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.9817(3) 0.11123(18) 0.75565(10) 0.0385(4) Uani 1 1 d . . . . .
H2A H 0.8770 0.0891 0.7842 0.058 Uiso 1 1 calc R U . . .
H2B H 1.0952 0.1229 0.7818 0.058 Uiso 1 1 calc R U . . .
H2C H 1.0028 0.0460 0.7239 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6887(2) 0.35209(16) 0.68205(7) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.7619 0.4218 0.7003 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4831(2) 0.36681(18) 0.70053(8) 0.0285(4) Uani 1 1 d . . . . .
H4 H 0.4125 0.2915 0.6884 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4568(3) 0.3923(3) 0.77246(9) 0.0500(6) Uani 1 1 d . . . . .
H5A H 0.5234 0.4672 0.7841 0.075 Uiso 1 1 calc R U . . .
H5B H 0.5073 0.3243 0.7979 0.075 Uiso 1 1 calc R U . . .
H5C H 0.3229 0.4018 0.7819 0.075 Uiso 1 1 calc R U . . .
C6 C 0.4256(2) 0.46066(15) 0.59678(8) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.3650 0.5339 0.5770 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6304(2) 0.46021(14) 0.57730(7) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.6420 0.4553 0.5289 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7170(2) 0.34781(13) 0.60856(7) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.8546 0.3472 0.5991 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4505(3) 0.23421(16) 0.56476(8) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.3330(2) 0.34769(16) 0.56828(8) 0.0281(3) Uani 1 1 d . . . . .
H10A H 0.2200 0.3293 0.5945 0.034 Uiso 1 1 calc R U . . .
H10B H 0.2900 0.3675 0.5237 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8865(3) 0.60069(16) 0.56941(10) 0.0336(4) Uani 1 1 d . . . . .
H11A H 0.8816 0.5795 0.5226 0.040 Uiso 1 1 calc R U . . .
H11B H 0.9919 0.5557 0.5896 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9147(3) 0.73585(15) 0.57757(8) 0.0297(4) Uani 1 1 d . . . . .
C13 C 1.0902(3) 0.78294(18) 0.59335(10) 0.0383(4) Uani 1 1 d . . . . .
H13 H 1.1930 0.7295 0.6004 0.046 Uiso 1 1 calc R U . . .
C14 C 1.1155(3) 0.90856(18) 0.59881(10) 0.0439(5) Uani 1 1 d . . . . .
H14 H 1.2356 0.9408 0.6089 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9653(4) 0.98535(17) 0.58943(9) 0.0431(5) Uani 1 1 d . . . . .
H15 H 0.9822 1.0708 0.5932 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7901(3) 0.93913(18) 0.57459(9) 0.0418(5) Uani 1 1 d . . . . .
H16 H 0.6869 0.9926 0.5687 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7656(3) 0.81529(17) 0.56838(9) 0.0345(4) Uani 1 1 d . . . . .
H17 H 0.6453 0.7839 0.5577 0.041 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 C1 1.198(2) . ?
O2 C1 1.346(2) . ?
O2 C3 1.442(2) . ?
O3 C6 1.4268(19) . ?
O3 C4 1.437(2) . ?
O4 C7 1.4153(18) . ?
O4 C11 1.425(2) . ?
O5 C9 1.350(2) . ?
O5 C8 1.4549(18) . ?
O6 C9 1.198(2) . ?
C1 C2 1.494(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.524(2) . ?
C3 C4 1.524(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.515(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.514(2) . ?
C6 C10 1.523(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.523(2) . ?
C7 H7 1.0000 . ?
C8 H8 1.0000 . ?
C9 C10 1.504(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.508(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.388(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 H17 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
C1 O2 C3 116.73(13) . . ?
C6 O3 C4 114.08(12) . . ?
C7 O4 C11 115.08(12) . . ?
C9 O5 C8 121.29(13) . . ?
O1 C1 O2 122.38(16) . . ?
O1 C1 C2 125.78(18) . . ?
O2 C1 C2 111.83(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C3 C8 111.53(13) . . ?
O2 C3 C4 105.80(13) . . ?
C8 C3 C4 112.18(13) . . ?
O2 C3 H3 109.1 . . ?
C8 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
O3 C4 C5 107.05(15) . . ?
O3 C4 C3 108.72(14) . . ?
C5 C4 C3 112.41(15) . . ?
O3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 C7 110.51(12) . . ?
O3 C6 C10 113.29(13) . . ?
C7 C6 C10 108.30(13) . . ?
O3 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
C10 C6 H6 108.2 . . ?
O4 C7 C6 108.51(12) . . ?
O4 C7 C8 111.77(12) . . ?
C6 C7 C8 106.40(13) . . ?
O4 C7 H7 110.0 . . ?
C6 C7 H7 110.0 . . ?
C8 C7 H7 110.0 . . ?
O5 C8 C7 110.14(12) . . ?
O5 C8 C3 110.56(12) . . ?
C7 C8 C3 109.81(12) . . ?
O5 C8 H8 108.8 . . ?
C7 C8 H8 108.8 . . ?
C3 C8 H8 108.8 . . ?
O6 C9 O5 117.36(17) . . ?
O6 C9 C10 122.63(17) . . ?
O5 C9 C10 119.97(14) . . ?
C9 C10 C6 116.92(14) . . ?
C9 C10 H10A 108.1 . . ?
C6 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
C6 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O4 C11 C12 107.95(14) . . ?
O4 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O4 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C17 C12 C13 119.09(17) . . ?
C17 C12 C11 120.15(18) . . ?
C13 C12 C11 120.76(18) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.55(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?

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 O2 C1 O1 -3.9(2) . . . . ?
C3 O2 C1 C2 177.24(14) . . . . ?
C1 O2 C3 C8 77.39(17) . . . . ?
C1 O2 C3 C4 -160.38(13) . . . . ?
C6 O3 C4 C5 178.50(15) . . . . ?
C6 O3 C4 C3 56.83(17) . . . . ?
O2 C3 C4 O3 -173.89(12) . . . . ?
C8 C3 C4 O3 -52.07(18) . . . . ?
O2 C3 C4 C5 67.8(2) . . . . ?
C8 C3 C4 C5 -170.40(16) . . . . ?
C4 O3 C6 C7 -63.86(17) . . . . ?
C4 O3 C6 C10 57.88(17) . . . . ?
C11 O4 C7 C6 -161.07(14) . . . . ?
C11 O4 C7 C8 81.91(17) . . . . ?
O3 C6 C7 O4 -58.87(16) . . . . ?
C10 C6 C7 O4 176.49(12) . . . . ?
O3 C6 C7 C8 61.55(16) . . . . ?
C10 C6 C7 C8 -63.10(15) . . . . ?
C9 O5 C8 C7 -35.74(18) . . . . ?
C9 O5 C8 C3 85.80(16) . . . . ?
O4 C7 C8 O5 -177.21(12) . . . . ?
C6 C7 C8 O5 64.50(15) . . . . ?
O4 C7 C8 C3 60.80(16) . . . . ?
C6 C7 C8 C3 -57.49(15) . . . . ?
O2 C3 C8 O5 51.78(16) . . . . ?
C4 C3 C8 O5 -66.70(17) . . . . ?
O2 C3 C8 C7 173.52(12) . . . . ?
C4 C3 C8 C7 55.03(18) . . . . ?
C8 O5 C9 O6 -176.57(15) . . . . ?
C8 O5 C9 C10 5.7(2) . . . . ?
O6 C9 C10 C6 177.09(17) . . . . ?
O5 C9 C10 C6 -5.3(2) . . . . ?
O3 C6 C10 C9 -88.15(17) . . . . ?
C7 C6 C10 C9 34.82(19) . . . . ?
C7 O4 C11 C12 156.85(14) . . . . ?
O4 C11 C12 C17 -43.4(2) . . . . ?
O4 C11 C12 C13 137.65(17) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 178.06(18) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C12 0.7(3) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C11 C12 C17 C16 -178.89(18) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038

