# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_19052511
_audit_block_doi                 10.5517/ccdc.csd.cc22dyq5
_database_code_depnum_ccdc_archive 'CCDC 1919077'
loop_
_audit_author_name
_audit_author_address
Y-ZA
;South China Normal University
China
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 O6, H2 O'
_chemical_formula_sum            'C10 H12 O7'
_chemical_formula_weight         244.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     A-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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7136(4)
_cell_length_b                   8.6961(5)
_cell_length_c                   9.1169(5)
_cell_angle_alpha                68.073(5)
_cell_angle_beta                 79.306(4)
_cell_angle_gamma                64.143(5)
_cell_volume                     510.32(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9230
_cell_measurement_theta_min      6.3730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.060
_diffrn_reflns_theta_min         5.232
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  31.00   1.00    1.00    --  -41.14  57.00-120.00   95
  2  ω   -107.00 -15.00   1.00    1.00    --  -41.14 -57.00  90.00   92
  3  ω    -86.00 -55.00   1.00    1.00    --  -41.14 125.00 -60.00   31
  4  ω    -32.00  62.00   1.00    1.00    --   41.14 -38.00 -60.00   94
  5  ω     37.00 120.00   1.00    1.00    --  107.79 -61.00  30.00   83
  6  ω     36.00  79.00   1.00    1.00    --  107.79 -30.00   0.00   43
  7  ω     82.00 178.00   1.00    1.00    --  107.79  45.00-180.00   96
  8  ω     89.00 116.00   1.00    1.00    --  107.79  77.00   0.00   27
  9  ω     96.00 154.00   1.00    1.00    --  107.79 125.00  90.00   58
 10  ω    130.00 157.00   1.00    1.00    --  107.79  77.00   0.00   27
 11  ω     35.00 110.00   1.00    1.00    --  107.79-125.00 -30.00   75
 12  ω     79.00 111.00   1.00    1.00    --  107.79-125.00-180.00   32
 13  ω     33.00 105.00   1.00    1.00    --  107.79 -77.00-180.00   72
 14  ω     90.00 136.00   1.00    1.00    --  107.79 -30.00   0.00   46
 15  ω     26.00 107.00   1.00    1.00    --  107.79 -94.00   0.00   81
 16  ω     83.00 166.00   1.00    1.00    --  107.79  30.00 -90.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0116447000
_diffrn_orient_matrix_UB_12      -0.1927491000
_diffrn_orient_matrix_UB_13      0.0932912000
_diffrn_orient_matrix_UB_21      -0.2213081000
_diffrn_orient_matrix_UB_22      0.0756229000
_diffrn_orient_matrix_UB_23      0.0193227000
_diffrn_orient_matrix_UB_31      -0.0134509000
_diffrn_orient_matrix_UB_32      -0.0254090000
_diffrn_orient_matrix_UB_33      -0.1553336000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1855
_reflns_number_total             1991
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1991
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²+0.1445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1371
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Free rotating group:
 O007(H00H)
2.b Ternary CH refined with riding coordinates:
 C00F(H00F)
2.c Idealised Me refined as rotating group:
 C00G(H00A,H00B,H00C), C00H(H00D,H00E,H00G)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003), O004(H004)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.31692(15) 0.82949(14) 0.25910(12) 0.0175(3) Uani 1 1 d . . . . .
O002 O 0.23145(17) 0.83723(15) 0.56300(13) 0.0216(3) Uani 1 1 d . . . . .
H002 H 0.2642 0.9049 0.4843 0.032 Uiso 1 1 calc GR . . . .
O003 O 0.33879(18) 0.52927(15) 0.19215(13) 0.0225(3) Uani 1 1 d . . . . .
H003 H 0.3600 0.6172 0.1328 0.034 Uiso 1 1 calc GR . . . .
O004 O 0.34154(16) 0.13200(15) 0.84245(13) 0.0223(3) Uani 1 1 d . . . . .
H004 H 0.4423 0.1457 0.8112 0.033 Uiso 1 1 calc GR . . . .
O005 O 0.23027(17) 0.13927(15) 0.62061(13) 0.0237(3) Uani 1 1 d . . . . .
O006 O 0.29920(17) 0.16173(16) 0.36645(14) 0.0260(3) Uani 1 1 d . . . . .
O007 O 0.4314(2) 0.75505(17) -0.05701(16) 0.0380(4) Uani 1 1 d . . . . .
H00H H 0.4193 0.8645 -0.0928 0.057 Uiso 1 1 d G . . . .
C008 C 0.2278(2) 0.40914(19) 0.61592(18) 0.0159(3) Uani 1 1 d . . . . .
C009 C 0.3003(2) 0.53881(19) 0.33925(17) 0.0154(3) Uani 1 1 d . . . . .
C00A C 0.2431(2) 0.69403(19) 0.53032(18) 0.0161(3) Uani 1 1 d . . . . .
C00B C 0.2704(2) 0.3982(2) 0.46420(18) 0.0164(3) Uani 1 1 d . . . . .
C00C C 0.2112(2) 0.55308(19) 0.65634(17) 0.0164(3) Uani 1 1 d . . . . .
C00D C 0.2851(2) 0.68655(19) 0.37628(17) 0.0154(3) Uani 1 1 d . . . . .
C00E C 0.2716(2) 0.2282(2) 0.46761(19) 0.0192(4) Uani 1 1 d . . . . .
C00F C 0.2066(2) 0.2389(2) 0.72541(18) 0.0190(3) Uani 1 1 d . . . . .
H00F H 0.0766 0.2695 0.7736 0.023 Uiso 1 1 calc R . . . .
C00G C 0.1439(2) 0.9774(2) 0.18407(19) 0.0247(4) Uani 1 1 d . . . . .
H00A H 0.1727 1.0800 0.1204 0.037 Uiso 1 1 calc GR . . . .
H00B H 0.0481 1.0092 0.2636 0.037 Uiso 1 1 calc GR . . . .
H00C H 0.0959 0.9410 0.1183 0.037 Uiso 1 1 calc GR . . . .
C00H C 0.1581(2) 0.5633(2) 0.82089(19) 0.0237(4) Uani 1 1 d . . . . .
H00D H 0.0204 0.6179 0.8329 0.036 Uiso 1 1 calc GR . . . .
H00E H 0.2130 0.6351 0.8380 0.036 Uiso 1 1 calc GR . . . .
H00G H 0.2069 0.4435 0.8967 0.036 Uiso 1 1 calc GR . . . .
H00I H 0.494(4) 0.714(4) -0.126(3) 0.052(8) Uiso 1 1 d . . . . .


_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
O001 C00D 1.3872(16) . ?
O001 C00G 1.4449(18) . ?
O002 H002 0.8200 . ?
O002 C00A 1.3480(17) . ?
O003 H003 0.8200 . ?
O003 C009 1.3444(18) . ?
O004 H004 0.8200 . ?
O004 C00F 1.3833(19) . ?
O005 C00E 1.3746(19) . ?
O005 C00F 1.4532(18) . ?
O006 C00E 1.203(2) . ?
O007 H00H 0.8500 . ?
O007 H00I 0.82(3) . ?
C008 C00B 1.390(2) . ?
C008 C00C 1.381(2) . ?
C008 C00F 1.504(2) . ?
C009 C00B 1.398(2) . ?
C009 C00D 1.398(2) . ?
C00A C00C 1.410(2) . ?
C00A C00D 1.401(2) . ?
C00B C00E 1.463(2) . ?
C00C C00H 1.505(2) . ?
C00F H00F 0.9800 . ?
C00G H00A 0.9600 . ?
C00G H00B 0.9600 . ?
C00G H00C 0.9600 . ?
C00H H00D 0.9600 . ?
C00H H00E 0.9600 . ?
C00H H00G 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
C00D O001 C00G 114.09(11) . . ?
C00A O002 H002 109.5 . . ?
C009 O003 H003 109.5 . . ?
C00F O004 H004 109.5 . . ?
C00E O005 C00F 111.56(11) . . ?
H00H O007 H00I 103.7 . . ?
C00B C008 C00F 108.58(13) . . ?
C00C C008 C00B 124.63(14) . . ?
C00C C008 C00F 126.78(14) . . ?
O003 C009 C00B 120.26(13) . . ?
O003 C009 C00D 123.21(13) . . ?
C00B C009 C00D 116.52(14) . . ?
O002 C00A C00C 117.65(13) . . ?
O002 C00A C00D 120.88(13) . . ?
C00D C00A C00C 121.46(13) . . ?
C008 C00B C009 120.30(14) . . ?
C008 C00B C00E 108.67(13) . . ?
C009 C00B C00E 131.02(14) . . ?
C008 C00C C00A 114.94(13) . . ?
C008 C00C C00H 123.18(14) . . ?
C00A C00C C00H 121.86(13) . . ?
O001 C00D C009 119.81(13) . . ?
O001 C00D C00A 118.03(13) . . ?
C009 C00D C00A 122.14(13) . . ?
O005 C00E C00B 107.58(13) . . ?
O006 C00E O005 119.89(14) . . ?
O006 C00E C00B 132.53(15) . . ?
O004 C00F O005 108.98(12) . . ?
O004 C00F C008 115.30(12) . . ?
O004 C00F H00F 109.6 . . ?
O005 C00F C008 103.52(11) . . ?
O005 C00F H00F 109.6 . . ?
C008 C00F H00F 109.6 . . ?
O001 C00G H00A 109.5 . . ?
O001 C00G H00B 109.5 . . ?
O001 C00G H00C 109.5 . . ?
H00A C00G H00B 109.5 . . ?
H00A C00G H00C 109.5 . . ?
H00B C00G H00C 109.5 . . ?
C00C C00H H00D 109.5 . . ?
C00C C00H H00E 109.5 . . ?
C00C C00H H00G 109.5 . . ?
H00D C00H H00E 109.5 . . ?
H00D C00H H00G 109.5 . . ?
H00E C00H H00G 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.569
_oxdiff_exptl_absorpt_empirical_full_min 0.719
