# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_shx97
_database_code_depnum_ccdc_archive 'CCDC 2022967'
loop_
_audit_author_name
_audit_author_address
'Jie-Ping Wan' 'Jiangxi Normal University'
_audit_update_record             
;
2020-08-12 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O6'
_chemical_formula_sum            'C18 H16 O6'
_chemical_formula_weight         328.31

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1121(18)
_cell_length_b                   9.4374(19)
_cell_length_c                   10.647(2)
_cell_angle_alpha                95.85(3)
_cell_angle_beta                 104.17(3)
_cell_angle_gamma                111.98(3)
_cell_volume                     803.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5814
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_standards_number         image
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6624
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2936
_reflns_number_gt                2218
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0639P)²+0.1564P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2936
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65492(19) 0.45419(19) 0.91769(15) 0.0630(4) Uani 1 1 d . . .
O2 O 0.27116(17) 0.33512(17) 0.60270(18) 0.0672(5) Uani 1 1 d . . .
O3 O 1.01877(16) 0.84886(16) 0.93414(14) 0.0545(4) Uani 1 1 d . . .
O4 O 1.02576(14) 1.00869(16) 0.79210(13) 0.0493(3) Uani 1 1 d . . .
O5 O 0.48404(19) 1.06427(17) 0.6555(2) 0.0911(7) Uani 1 1 d . . .
O6 O 0.25682(15) 0.84237(15) 0.57657(14) 0.0521(4) Uani 1 1 d . . .
C1 C 0.8530(3) 0.3579(2) 0.8702(2) 0.0615(6) Uani 1 1 d . . .
H1A H 0.8414 0.2953 0.9323 0.074 Uiso 1 1 calc R . .
C2 C 0.9585(3) 0.3607(3) 0.7972(3) 0.0738(8) Uani 1 1 d . . .
H2A H 1.0173 0.2986 0.8099 0.089 Uiso 1 1 calc R . .
C3 C 0.9792(3) 0.4532(3) 0.7060(3) 0.0659(7) Uani 1 1 d . . .
H3A H 1.0510 0.4534 0.6570 0.079 Uiso 1 1 calc R . .
C4 C 0.8920(2) 0.5465(2) 0.6873(2) 0.0497(5) Uani 1 1 d . . .
H4A H 0.9066 0.6108 0.6266 0.060 Uiso 1 1 calc R . .
C5 C 0.7832(2) 0.54382(19) 0.75908(17) 0.0380(4) Uani 1 1 d . . .
C6 C 0.7642(2) 0.4486(2) 0.85077(19) 0.0459(5) Uani 1 1 d . . .
C7 C 0.6870(2) 0.64180(19) 0.73555(15) 0.0337(4) Uani 1 1 d . . .
C8 C 0.76754(19) 0.80563(19) 0.76656(16) 0.0354(4) Uani 1 1 d . . .
C9 C 0.6782(2) 0.8953(2) 0.73455(17) 0.0396(4) Uani 1 1 d . . .
H9A H 0.7332 1.0038 0.7550 0.048 Uiso 1 1 calc R . .
C10 C 0.5075(2) 0.82410(19) 0.67220(17) 0.0379(4) Uani 1 1 d . . .
C11 C 0.4265(2) 0.6636(2) 0.64336(17) 0.0388(4) Uani 1 1 d . . .
H11A H 0.3120 0.6160 0.6031 0.047 Uiso 1 1 calc R . .
C12 C 0.5139(2) 0.57105(19) 0.67375(16) 0.0363(4) Uani 1 1 d . . .
C13 C 0.6207(3) 0.3517(4) 1.0062(3) 0.0860(9) Uani 1 1 d . . .
H13A H 0.5426 0.3678 1.0458 0.129 Uiso 1 1 calc R . .
H13B H 0.7219 0.3730 1.0745 0.129 Uiso 1 1 calc R . .
H13C H 0.5747 0.2453 0.9582 0.129 Uiso 1 1 calc R . .
C14 C 0.4203(2) 0.3994(2) 0.63853(19) 0.0435(4) Uani 1 1 d . . .
H14A H 0.4799 0.3377 0.6444 0.052 Uiso 1 1 calc R . .
C15 C 0.9497(2) 0.8863(2) 0.84082(17) 0.0383(4) Uani 1 1 d . . .
C16 C 1.2006(2) 1.1001(3) 0.8613(2) 0.0627(6) Uani 1 1 d . . .
H16A H 1.2436 1.1847 0.8188 0.094 Uiso 1 1 calc R . .
H16B H 1.2597 1.0348 0.8593 0.094 Uiso 1 1 calc R . .
H16C H 1.2146 1.1416 0.9517 0.094 Uiso 1 1 calc R . .
C17 C 0.4175(2) 0.9251(2) 0.63512(19) 0.0448(4) Uani 1 1 d . . .
C18 C 0.1589(2) 0.9253(2) 0.5245(2) 0.0529(5) Uani 1 1 d . . .
H18A H 0.0449 0.8525 0.4845 0.079 Uiso 1 1 calc R . .
H18B H 0.2003 0.9766 0.4591 0.079 Uiso 1 1 calc R . .
H18C H 0.1665 1.0018 0.5953 0.079 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
O1 C6 1.371(2) . ?
O1 C13 1.423(3) . ?
O2 C14 1.201(2) . ?
O3 C15 1.200(2) . ?
O4 C15 1.335(2) . ?
O4 C16 1.446(2) . ?
O5 C17 1.192(2) . ?
O6 C17 1.319(2) . ?
O6 C18 1.443(2) . ?
C1 C2 1.371(4) . ?
C1 C6 1.380(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(3) . ?
C5 C7 1.494(2) . ?
C7 C8 1.402(2) . ?
C7 C12 1.408(2) . ?
C8 C9 1.390(2) . ?
C8 C15 1.500(2) . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.375(2) . ?
C10 C17 1.497(2) . ?
C11 C12 1.398(2) . ?
C11 H11A 0.9300 . ?
C12 C14 1.476(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C6 O1 C13 118.34(18) . . ?
C15 O4 C16 115.87(15) . . ?
C17 O6 C18 117.49(15) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 H1A 120.3 . . ?
C6 C1 H1A 120.3 . . ?
C1 C2 C3 121.43(18) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.41(16) . . ?
C4 C5 C7 119.47(16) . . ?
C6 C5 C7 121.12(15) . . ?
O1 C6 C1 124.35(19) . . ?
O1 C6 C5 115.40(15) . . ?
C1 C6 C5 120.2(2) . . ?
C8 C7 C12 118.41(15) . . ?
C8 C7 C5 121.08(14) . . ?
C12 C7 C5 120.39(15) . . ?
C9 C8 C7 120.50(15) . . ?
C9 C8 C15 119.16(15) . . ?
C7 C8 C15 120.28(14) . . ?
C8 C9 C10 120.61(16) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C11 C10 C9 119.53(15) . . ?
C11 C10 C17 121.73(15) . . ?
C9 C10 C17 118.73(16) . . ?
C10 C11 C12 120.88(15) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 120.07(15) . . ?
C11 C12 C14 118.33(15) . . ?
C7 C12 C14 121.60(15) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C12 123.45(16) . . ?
O2 C14 H14A 118.3 . . ?
C12 C14 H14A 118.3 . . ?
O3 C15 O4 123.83(16) . . ?
O3 C15 C8 124.81(17) . . ?
O4 C15 C8 111.34(14) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O6 124.08(16) . . ?
O5 C17 C10 123.68(16) . . ?
O6 C17 C10 112.23(15) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C7 -178.48(17) . . . . ?
C13 O1 C6 C1 -4.8(3) . . . . ?
C13 O1 C6 C5 175.71(19) . . . . ?
C2 C1 C6 O1 179.69(18) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C4 C5 C6 O1 179.61(16) . . . . ?
C7 C5 C6 O1 -1.1(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C7 C5 C6 C1 179.40(16) . . . . ?
C4 C5 C7 C8 -65.4(2) . . . . ?
C6 C5 C7 C8 115.31(19) . . . . ?
C4 C5 C7 C12 110.58(19) . . . . ?
C6 C5 C7 C12 -68.7(2) . . . . ?
C12 C7 C8 C9 -1.2(2) . . . . ?
C5 C7 C8 C9 174.88(15) . . . . ?
C12 C7 C8 C15 175.75(15) . . . . ?
C5 C7 C8 C15 -8.2(2) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C15 C8 C9 C10 -176.47(16) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C17 -177.78(16) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C17 C10 C11 C12 177.27(16) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C10 C11 C12 C14 -179.10(16) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C5 C7 C12 C11 -175.37(15) . . . . ?
C8 C7 C12 C14 -179.76(15) . . . . ?
C5 C7 C12 C14 4.2(2) . . . . ?
C11 C12 C14 O2 -11.0(3) . . . . ?
C7 C12 C14 O2 169.48(18) . . . . ?
C16 O4 C15 O3 -1.6(3) . . . . ?
C16 O4 C15 C8 176.78(16) . . . . ?
C9 C8 C15 O3 134.62(19) . . . . ?
C7 C8 C15 O3 -42.3(2) . . . . ?
C9 C8 C15 O4 -43.8(2) . . . . ?
C7 C8 C15 O4 139.29(16) . . . . ?
C18 O6 C17 O5 5.3(3) . . . . ?
C18 O6 C17 C10 -174.15(16) . . . . ?
C11 C10 C17 O5 -178.1(2) . . . . ?
C9 C10 C17 O5 0.4(3) . . . . ?
C11 C10 C17 O6 1.4(3) . . . . ?
C9 C10 C17 O6 179.84(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
