# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1960998'
loop_
_audit_author_name
_audit_author_address
'shuanglin qin'
;Tianjin University
China
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H18 O7), 0.5(C2 H8 O2), 2(H2O)'
_chemical_formula_sum            'C29 H44 O17'
_chemical_formula_weight         664.64

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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   11.3217(3)
_cell_length_b                   30.9860(7)
_cell_length_c                   4.67920(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.53(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3077
_cell_measurement_theta_min      5.8000
_cell_measurement_theta_max      72.7540

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.951
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6637
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_theta_min         4.157
_diffrn_reflns_theta_max         73.634
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3181
_reflns_number_gt                2845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.994

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0866P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3181
_refine_ls_number_parameters     230
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.068
_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 1.2283(3) 0.45127(8) 0.4511(6) 0.0409(6) Uani 1 1 d D . . . .
O1W O 0.7300(2) 0.50669(8) 0.9485(5) 0.0342(6) Uani 1 1 d . . . A -1
H1WA H 0.738786 0.520061 0.791367 0.051 Uiso 1 1 d R U . A -1
H1WB H 0.656636 0.505361 0.986267 0.051 Uiso 1 1 d R U . A -1
O2 O 0.9676(3) 0.45790(8) 0.4034(5) 0.0415(7) Uani 1 1 d D . . . .
H2 H 0.938(4) 0.4436(13) 0.266(7) 0.062 Uiso 1 1 d D U . . .
O3 O 0.8275(2) 0.42783(7) 0.9834(5) 0.0370(6) Uani 1 1 d D . . . .
H3 H 0.802(3) 0.4537(6) 0.969(9) 0.055 Uiso 1 1 d D U . . .
O4 O 0.5812(2) 0.38754(10) 0.8213(7) 0.0542(8) Uani 1 1 d . . . . .
O5 O 0.6263(2) 0.34792(9) 1.2056(6) 0.0461(7) Uani 1 1 d . . . . .
O6 O 0.8429(2) 0.33197(7) 1.0182(4) 0.0299(5) Uani 1 1 d . . . . .
O7 O 1.0143(2) 0.36337(6) 0.8441(5) 0.0286(5) Uani 1 1 d . . . . .
O8 O 0.500000 0.500000 0.0976(10) 0.110(3) Uani 1 2 d DS T P . .
H8A H 0.437000 0.500000 -0.009934 0.164 Uiso 0.5 1 d DR U P C .
C1' C 0.3973(12) 0.3695(6) 0.903(4) 0.061(2) Uani 0.308(8) 1 d . U P B 2
H1'A H 0.360937 0.360349 0.728396 0.092 Uiso 0.308(8) 1 calc R U P B 2
H1'B H 0.355358 0.393967 0.978403 0.092 Uiso 0.308(8) 1 calc R U P B 2
H1'C H 0.394940 0.346377 1.039709 0.092 Uiso 0.308(8) 1 calc R U P B 2
C1 C 0.4668(5) 0.3958(3) 0.9389(15) 0.061(2) Uani 0.692(8) 1 d . U P B 1
H1A H 0.417950 0.370722 0.916109 0.092 Uiso 0.692(8) 1 calc R U P B 1
H1B H 0.431383 0.419785 0.841069 0.092 Uiso 0.692(8) 1 calc R U P B 1
H1C H 0.474202 0.402505 1.138421 0.092 Uiso 0.692(8) 1 calc R U P B 1
C2 C 0.6518(3) 0.36287(11) 0.9794(7) 0.0353(8) Uani 1 1 d . . . . .
C3 C 0.7692(3) 0.35655(10) 0.8284(7) 0.0291(7) Uani 1 1 d . . . . .
H3A H 0.755642 0.339586 0.654724 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8278(3) 0.39928(10) 0.7446(6) 0.0287(7) Uani 1 1 d . . . . .
H4 H 0.782608 0.412450 0.588715 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9521(3) 0.38947(10) 0.6387(6) 0.0282(7) Uani 1 1 d . . . . .
H5 H 0.946002 0.373219 0.459656 0.034 Uiso 1 1 calc R U . . .
C6 C 1.0287(3) 0.42884(10) 0.5868(6) 0.0302(7) Uani 1 1 d . . . . .
H6 H 1.042516 0.443254 0.770230 0.036 Uiso 1 1 calc R U . . .
C7 C 1.1470(3) 0.41631(11) 0.4605(8) 0.0364(8) Uani 1 1 d . . . . .
H7A H 1.180806 0.393142 0.573504 0.044 Uiso 1 1 calc R U . . .
H7B H 1.134947 0.405493 0.268209 0.044 Uiso 1 1 calc R U . . .
C8 C 0.9542(3) 0.32384(10) 0.8908(6) 0.0287(7) Uani 1 1 d . . . . .
H8 H 0.943215 0.308764 0.708596 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0245(3) 0.29616(10) 1.0912(6) 0.0298(7) Uani 1 1 d . . . . .
C10 C 0.9742(3) 0.25861(11) 1.1993(7) 0.0356(8) Uani 1 1 d . . . . .
H10 H 0.897897 0.250838 1.146482 0.043 Uiso 1 1 calc R U . . .
C11 C 1.0381(4) 0.23266(11) 1.3865(8) 0.0395(9) Uani 1 1 d . . . . .
H11 H 1.004172 0.207547 1.457996 0.047 Uiso 1 1 calc R U . . .
C12 C 1.1517(4) 0.24391(11) 1.4671(7) 0.0396(8) Uani 1 1 d . . . . .
H12 H 1.193198 0.226973 1.596815 0.047 Uiso 1 1 calc R U . . .
C13 C 1.2024(4) 0.28046(12) 1.3532(9) 0.0423(9) Uani 1 1 d . . . . .
H13 H 1.279250 0.287904 1.403344 0.051 Uiso 1 1 calc R U . . .
C14 C 1.1392(3) 0.30645(11) 1.1628(8) 0.0388(8) Uani 1 1 d . . . . .
H14 H 1.174681 0.330775 1.084086 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4787(10) 0.5152(4) 0.3938(18) 0.067(4) Uani 0.5 1 d . . P C -1
H15A H 0.547468 0.530086 0.462457 0.100 Uiso 0.5 1 calc R U P C -1
H15B H 0.462597 0.490905 0.514954 0.100 Uiso 0.5 1 calc R U P C -1
H15C H 0.412307 0.534469 0.395733 0.100 Uiso 0.5 1 calc R U P C -1
H1 H 1.235(6) 0.4651(19) 0.295(8) 0.100 Uiso 1 1 d D 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 C7 1.422(4) . ?
O1 H1 0.850(13) . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8501 . ?
O2 C6 1.423(4) . ?
O2 H2 0.850(13) . ?
O3 C4 1.425(4) . ?
O3 H3 0.856(13) . ?
O4 C2 1.331(4) . ?
O4 C1 1.431(6) . ?
O4 C1' 2.189(15) . ?
O5 C2 1.191(4) . ?
O6 C8 1.416(4) . ?
O6 C3 1.437(4) . ?
O7 C8 1.418(4) . ?
O7 C5 1.440(4) . ?
O8 C15 1.484(9) . ?
O8 H8A 0.8729 . ?
O8 H8A 0.8729 2_665 ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.517(5) . ?
C3 C4 1.532(4) . ?
C3 H3A 0.9800 . ?
C4 C5 1.522(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.517(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.515(5) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.500(4) . ?
C8 H8 0.9800 . ?
C9 C14 1.379(5) . ?
C9 C10 1.391(4) . ?
C10 C11 1.392(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C7 O1 H1 118(5) . . ?
H1WA O1W H1WB 108.5 . . ?
C6 O2 H2 109(3) . . ?
C4 O3 H3 121(3) . . ?
C2 O4 C1 115.7(3) . . ?
C2 O4 C1' 109.1(4) . . ?
C8 O6 C3 110.5(2) . . ?
C8 O7 C5 110.7(2) . . ?
C15 O8 H8A 113.9 . . ?
C15 O8 H8A 132.2(4) . 2_665 ?
H8A O8 H8A 109.6 . 2_665 ?
O4 C1' H1'A 109.5 . . ?
O4 C1' H1'B 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
O4 C1' H1'C 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O4 C1 H1A 109.5 . . ?
O4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5 C2 O4 124.8(4) . . ?
O5 C2 C3 125.2(3) . . ?
O4 C2 C3 110.0(3) . . ?
O6 C3 C2 106.8(2) . . ?
O6 C3 C4 111.4(3) . . ?
C2 C3 C4 112.8(3) . . ?
O6 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
O3 C4 C5 112.4(3) . . ?
O3 C4 C3 109.5(3) . . ?
C5 C4 C3 108.1(3) . . ?
O3 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
O7 C5 C6 106.2(2) . . ?
O7 C5 C4 110.3(3) . . ?
C6 C5 C4 114.9(3) . . ?
O7 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
O2 C6 C7 110.9(3) . . ?
O2 C6 C5 109.1(3) . . ?
C7 C6 C5 111.2(3) . . ?
O2 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
O1 C7 C6 112.9(3) . . ?
O1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O6 C8 O7 109.8(2) . . ?
O6 C8 C9 108.1(2) . . ?
O7 C8 C9 109.6(3) . . ?
O6 C8 H8 109.8 . . ?
O7 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C14 C9 C10 119.4(3) . . ?
C14 C9 C8 121.3(3) . . ?
C10 C9 C8 119.2(3) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O8 C15 H15A 109.5 . . ?
O8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C1 O4 C2 O5 -0.2(7) . . . . ?
C1' O4 C2 O5 -29.7(7) . . . . ?
C1 O4 C2 C3 179.6(5) . . . . ?
C1' O4 C2 C3 150.1(6) . . . . ?
C8 O6 C3 C2 178.9(2) . . . . ?
C8 O6 C3 C4 -57.6(3) . . . . ?
O5 C2 C3 O6 -3.6(5) . . . . ?
O4 C2 C3 O6 176.6(3) . . . . ?
O5 C2 C3 C4 -126.3(4) . . . . ?
O4 C2 C3 C4 53.9(4) . . . . ?
O6 C3 C4 O3 -71.7(3) . . . . ?
C2 C3 C4 O3 48.4(4) . . . . ?
O6 C3 C4 C5 51.2(3) . . . . ?
C2 C3 C4 C5 171.2(2) . . . . ?
C8 O7 C5 C6 -175.3(2) . . . . ?
C8 O7 C5 C4 59.6(3) . . . . ?
O3 C4 C5 O7 69.3(3) . . . . ?
C3 C4 C5 O7 -51.7(3) . . . . ?
O3 C4 C5 C6 -50.6(3) . . . . ?
C3 C4 C5 C6 -171.6(3) . . . . ?
O7 C5 C6 O2 -175.1(2) . . . . ?
C4 C5 C6 O2 -52.9(3) . . . . ?
O7 C5 C6 C7 62.2(3) . . . . ?
C4 C5 C6 C7 -175.6(3) . . . . ?
O2 C6 C7 O1 67.8(4) . . . . ?
C5 C6 C7 O1 -170.6(3) . . . . ?
C3 O6 C8 O7 63.5(3) . . . . ?
C3 O6 C8 C9 -177.0(2) . . . . ?
C5 O7 C8 O6 -64.9(3) . . . . ?
C5 O7 C8 C9 176.5(2) . . . . ?
O6 C8 C9 C14 -131.0(3) . . . . ?
O7 C8 C9 C14 -11.4(4) . . . . ?
O6 C8 C9 C10 51.1(4) . . . . ?
O7 C8 C9 C10 170.7(3) . . . . ?
C14 C9 C10 C11 2.4(5) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -2.0(5) . . . . ?
C11 C12 C13 C14 1.3(6) . . . . ?
C10 C9 C14 C13 -3.1(5) . . . . ?
C8 C9 C14 C13 179.1(3) . . . . ?
C12 C13 C14 C9 1.2(6) . . . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059



