# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_gsy2021329-s
_database_code_depnum_ccdc_archive 'CCDC 2089219'
loop_
_audit_author_name
_audit_author_address
'Shaoyan Gan'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_audit_creation_date             2021-03-30
_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         'C14 H10 O6'
_chemical_formula_sum            'C14 H10 O6'
_chemical_formula_weight         274.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5207(4)
_cell_length_b                   11.7590(3)
_cell_length_c                   7.7352(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.600(2)
_cell_angle_gamma                90
_cell_volume                     1219.02(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    229.99(10)
_cell_measurement_theta_max      71.4030
_cell_measurement_theta_min      3.2610
_shelx_estimated_absorpt_T_max   0.823
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.779
_diffrn_reflns_theta_min         3.298
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      229.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00  81.00   0.50    0.05    --    0.00  32.00-109.00   50
  2  ω    100.00 126.00   0.50    0.05    --   55.87  32.00-109.00   52
  3  ω    106.00 131.00   0.50    0.05    --  111.74  32.00-109.00   50
  4  ω     81.00 129.00   0.50    0.05    --   55.87 125.00-180.00   96
  5  ω     47.00 146.00   0.50    0.05    --  111.74 178.00 -90.00  198
  6  ω     86.00 137.00   0.50    0.05    --   55.87 125.00  90.00  102
  7  ω     79.00 118.00   0.50    0.05    --   55.87 125.00 120.00   78
  8  ω     58.00 145.00   0.50    0.05    --  111.74 178.00  90.00  174
  9  ω     35.00  60.00   0.50    0.05    --  111.74  32.00-109.00   50
 10  ω    128.00 153.00   0.50    0.05    --  111.74 -50.00-180.00   50
 11  ω     66.00 111.00   0.50    0.05    --   55.87-125.00 -60.00   90
 12  ω     34.00  60.00   0.50    0.05    --   55.87-125.00 -60.00   52
 13  ω     23.00  69.00   0.50    0.05    --  111.74-111.00 -30.00   92
 14  ω     18.00 101.00   0.50    0.05    --  111.74 -91.00-120.00  166
 15  ω     28.00 117.00   0.50    0.05    --  111.74 -50.00-180.00  178
 16  ω     22.00  47.00   0.50    0.05    --    0.00  32.00-109.00   50
 17  ω    -33.00 124.00   0.50    0.05    --   55.87 -32.00  90.00  314
 18  ω     82.00 108.00   0.50    0.05    --  111.74 -32.00  90.00   52
 19  ω     61.00 106.00   0.50    0.05    --  111.74-111.00 120.00   90
 20  ω     22.00  47.00   0.50    0.05    --  111.74-111.00 120.00   50
 21  ω     22.00  47.00   0.50    0.05    --  111.74 -32.00  90.00   50
 22  ω    -76.00 -28.00   0.50    0.05    --    0.00  32.00-109.00   96
 23  ω   -127.00 -70.00   0.50    0.05    -- -102.00 -32.00  90.00  114
 24  ω    -62.00 -19.00   0.50    0.05    -- -102.00  37.00 120.00   86
 25  ω   -159.00-107.00   0.50    0.05    -- -102.00  37.00 120.00  104
 26  ω   -173.00-131.00   0.50    0.05    -- -102.00 -32.00  90.00   84
 27  ω    -83.00 -46.00   0.50    0.05    --    0.00 178.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0873881000
_diffrn_orient_matrix_UB_12      0.0529274000
_diffrn_orient_matrix_UB_13      0.1213835000
_diffrn_orient_matrix_UB_21      0.0666280000
_diffrn_orient_matrix_UB_22      -0.0091284000
_diffrn_orient_matrix_UB_23      -0.1463505000
_diffrn_orient_matrix_UB_31      -0.0336637000
_diffrn_orient_matrix_UB_32      0.1195138000
_diffrn_orient_matrix_UB_33      -0.0649422000
_diffrn_oxdiff_digest_frames     
;
0154c746d4d3f3abecfc313b8bad72b4df0005043a2
;
_diffrn_oxdiff_digest_hkl        
;
017d8e9ce8ba08efe582c8342380cb4e4b32f2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2081
_reflns_number_total             2317
_reflns_odcompleteness_completeness 99.91
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.320
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.052
_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)+(0.0993P)²+0.3424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1525
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6A), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.24937(10) 0.50463(11) 0.59415(16) 0.0399(3) Uani 1 1 d . . . . .
O2 O 0.14800(9) 0.63574(10) 0.44931(16) 0.0372(3) Uani 1 1 d . . . . .
O3 O 0.17803(10) 0.70603(11) 0.60072(18) 0.0433(4) Uani 1 1 d . . . . .
H3 H 0.2158 0.7561 0.5754 0.065 Uiso 1 1 calc GR . . . .
O4 O 0.31301(13) 0.63527(12) 0.23226(18) 0.0533(4) Uani 1 1 d . . . . .
O5 O 0.33120(13) 0.52928(12) 0.00001(17) 0.0532(4) Uani 1 1 d . . . . .
O6 O 0.29058(14) 0.62989(13) -0.09421(19) 0.0606(5) Uani 1 1 d . . . . .
H6 H 0.2740 0.6137 -0.1971 0.091 Uiso 1 1 calc GR . . . .
C1 C 0.18985(12) 0.53142(14) 0.4715(2) 0.0307(4) Uani 1 1 d . . . . .
C2 C 0.14688(12) 0.45466(14) 0.3280(2) 0.0312(4) Uani 1 1 d . . . . .
C3 C 0.20397(12) 0.36892(14) 0.2644(2) 0.0312(4) Uani 1 1 d . . . . .
C4 C 0.15563(15) 0.28974(17) 0.1483(3) 0.0410(4) Uani 1 1 d . . . . .
H4 H 0.1919 0.2301 0.1089 0.049 Uiso 1 1 calc R . . . .
C5 C 0.05415(15) 0.29869(19) 0.0908(3) 0.0474(5) Uani 1 1 d . . . . .
H5 H 0.0233 0.2458 0.0119 0.057 Uiso 1 1 calc R . . . .
C6 C -0.00089(14) 0.38530(19) 0.1499(3) 0.0474(5) Uani 1 1 d . . . . .
H6A H -0.0687 0.3913 0.1102 0.057 Uiso 1 1 calc R . . . .
C7 C 0.04458(13) 0.46356(17) 0.2684(2) 0.0394(4) Uani 1 1 d . . . . .
H7 H 0.0073 0.5220 0.3086 0.047 Uiso 1 1 calc R . . . .
C8 C 0.31473(12) 0.35934(14) 0.3099(2) 0.0308(4) Uani 1 1 d . . . . .
C9 C 0.37854(12) 0.44501(14) 0.2663(2) 0.0298(4) Uani 1 1 d . . . . .
C10 C 0.48160(13) 0.43509(17) 0.3065(2) 0.0389(4) Uani 1 1 d . . . . .
H10 H 0.5232 0.4932 0.2781 0.047 Uiso 1 1 calc R . . . .
C11 C 0.52161(14) 0.33815(18) 0.3890(3) 0.0448(5) Uani 1 1 d . . . . .
H11 H 0.5903 0.3318 0.4189 0.054 Uiso 1 1 calc R . . . .
C12 C 0.46010(15) 0.25106(18) 0.4269(2) 0.0447(5) Uani 1 1 d . . . . .
H12 H 0.4876 0.1852 0.4799 0.054 Uiso 1 1 calc R . . . .
C13 C 0.35733(14) 0.26066(16) 0.3866(2) 0.0406(4) Uani 1 1 d . . . . .
H13 H 0.3165 0.2007 0.4111 0.049 Uiso 1 1 calc R . . . .
C14 C 0.33680(12) 0.54841(14) 0.1711(2) 0.0291(4) Uani 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
O1 C1 1.202(2) . ?
O2 O3 1.4470(17) . ?
O2 C1 1.352(2) . ?
O4 C14 1.188(2) . ?
O5 O6 1.4583(18) . ?
O5 C14 1.335(2) . ?
C1 C2 1.488(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.403(2) . ?
C3 C4 1.395(2) . ?
C3 C8 1.497(2) . ?
C4 C5 1.389(3) . ?
C5 C6 1.375(3) . ?
C6 C7 1.384(3) . ?
C8 C9 1.396(2) . ?
C8 C13 1.393(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.493(2) . ?
C10 C11 1.381(3) . ?
C11 C12 1.375(3) . ?
C12 C13 1.388(3) . ?

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 O3 110.32(12) . . ?
C14 O5 O6 109.09(13) . . ?
O1 C1 O2 124.28(16) . . ?
O1 C1 C2 125.76(16) . . ?
O2 C1 C2 109.88(14) . . ?
C3 C2 C1 121.38(15) . . ?
C3 C2 C7 120.29(16) . . ?
C7 C2 C1 118.07(15) . . ?
C2 C3 C8 123.59(14) . . ?
C4 C3 C2 118.32(16) . . ?
C4 C3 C8 118.06(15) . . ?
C5 C4 C3 120.97(18) . . ?
C6 C5 C4 120.31(17) . . ?
C5 C6 C7 120.01(17) . . ?
C6 C7 C2 120.01(18) . . ?
C9 C8 C3 121.32(14) . . ?
C13 C8 C3 120.49(15) . . ?
C13 C8 C9 118.04(15) . . ?
C8 C9 C14 120.09(14) . . ?
C10 C9 C8 121.19(16) . . ?
C10 C9 C14 118.71(15) . . ?
C11 C10 C9 119.46(17) . . ?
C12 C11 C10 120.14(17) . . ?
C11 C12 C13 120.49(17) . . ?
C12 C13 C8 120.58(17) . . ?
O4 C14 O5 123.85(16) . . ?
O4 C14 C9 127.48(15) . . ?
O5 C14 C9 108.66(14) . . ?

_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 2.058
_oxdiff_exptl_absorpt_empirical_full_min 0.321
