# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_test2
_audit_block_doi                 10.5517/ccdc.csd.cc2jzkgk
_database_code_depnum_ccdc_archive 'CCDC 2353069'
loop_
_audit_author_name
_audit_author_address
Xia
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-05-04 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2024-01-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 O8, H2 O'
_chemical_formula_sum            'C20 H20 O9'
_chemical_formula_weight         404.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.9192(2)
_cell_length_b                   11.9987(3)
_cell_length_c                   21.8472(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2075.92(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7890
_cell_measurement_temperature    296
_cell_measurement_theta_max      99
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       clear_block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12803
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.081
_diffrn_reflns_theta_min         4.047
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                3431
_reflns_number_total             3950
_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 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.053
_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)+(0.0772P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1241
_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, All O(H,H) groups
2.a Free rotating group:
 O008(H00N,H00Q)
2.b Ternary CH refined with riding coordinates:
 C00E(H00E), C00F(H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
 C00P(H00P), C00R(H00R)
2.d Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C00T(H00D,H00G,H00I)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003), O007(H007)
;
_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 0.5205(2) 0.95904(14) 0.51499(8) 0.0499(4) Uani 1 1 d . . . . .
O002 O 0.4498(2) 0.82274(14) 0.61441(9) 0.0516(4) Uani 1 1 d . . . . .
O003 O 0.8241(2) 0.9238(2) 0.55158(11) 0.0683(6) Uani 1 1 d . . . . .
H003 H 0.921769 0.916049 0.563337 0.102 Uiso 1 1 calc R U . . .
O004 O 0.1450(2) 0.89652(18) 0.57953(13) 0.0731(6) Uani 1 1 d . . . . .
O005 O 0.6137(3) 1.12278(16) 0.48012(11) 0.0696(6) Uani 1 1 d . . . . .
O006 O 0.3150(3) 0.80516(19) 0.70416(11) 0.0744(6) Uani 1 1 d . . . . .
O007 O 0.2270(3) 1.07424(16) 0.58553(13) 0.0720(6) Uani 1 1 d . . . . .
H007 H 0.128382 1.087478 0.576644 0.108 Uiso 1 1 calc R U . . .
O008 O -0.0432(3) 1.16810(18) 0.54249(15) 0.0832(7) Uani 1 1 d G . . . .
H00N H -0.031347 1.236552 0.533507 0.125 Uiso 1 1 d G U . . .
H00Q H -0.126248 1.146513 0.520845 0.125 Uiso 1 1 d G U . . .
O009 O 0.7742(3) 0.9682(3) 0.64906(12) 0.0928(8) Uani 1 1 d . . . . .
C00A C 0.3897(3) 0.7619(2) 0.66232(12) 0.0518(6) Uani 1 1 d . . . . .
C00B C 0.4295(3) 0.6429(2) 0.65597(12) 0.0515(6) Uani 1 1 d . . . . .
C00C C 0.2474(3) 0.9662(2) 0.59189(13) 0.0522(6) Uani 1 1 d . . . . .
C00D C 0.5554(3) 1.0309(2) 0.46973(13) 0.0516(6) Uani 1 1 d . . . . .
C00E C 0.4214(3) 0.9391(2) 0.61610(13) 0.0492(6) Uani 1 1 d . . . . .
H00E H 0.432063 0.966074 0.658260 0.059 Uiso 1 1 calc R U . . .
C00F C 0.5548(3) 0.9927(2) 0.57656(12) 0.0489(6) Uani 1 1 d . . . . .
H00F H 0.543717 1.073831 0.579450 0.059 Uiso 1 1 calc R U . . .
C00G C 0.7309(3) 0.9596(2) 0.59685(14) 0.0561(6) Uani 1 1 d . . . . .
C00H C 0.4830(4) 0.8725(3) 0.40079(14) 0.0626(7) Uani 1 1 d . . . . .
H00H H 0.492198 0.823694 0.433696 0.075 Uiso 1 1 calc R U . . .
C00I C 0.5120(3) 0.9859(2) 0.40930(13) 0.0534(6) Uani 1 1 d . . . . .
C00J C 0.5425(4) 0.4881(3) 0.60015(17) 0.0715(8) Uani 1 1 d . . . . .
H00J H 0.593396 0.460181 0.564980 0.086 Uiso 1 1 calc R U . . .
C00K C 0.5082(4) 0.6001(3) 0.60373(15) 0.0635(7) Uani 1 1 d . . . . .
H00K H 0.537171 0.647216 0.571603 0.076 Uiso 1 1 calc R U . . .
C00L C 0.4249(5) 0.4588(3) 0.69907(17) 0.0717(8) Uani 1 1 d . . . . .
H00L H 0.396539 0.411401 0.731143 0.086 Uiso 1 1 calc R U . . .
C00M C 0.3885(4) 0.5709(3) 0.70339(15) 0.0630(7) Uani 1 1 d . . . . .
H00M H 0.335999 0.598454 0.738336 0.076 Uiso 1 1 calc R U . . .
C00N C 0.5037(4) 0.4157(3) 0.64716(18) 0.0702(8) Uani 1 1 d . . . . .
C00O C 0.4408(5) 0.8325(3) 0.34384(16) 0.0761(9) Uani 1 1 d . . . . .
H00O H 0.421803 0.756653 0.338496 0.091 Uiso 1 1 calc R U . . .
C00P C 0.4998(5) 1.0573(3) 0.35977(16) 0.0747(9) Uani 1 1 d . . . . .
H00P H 0.521622 1.132932 0.364632 0.090 Uiso 1 1 calc R U . . .
C00Q C 0.4262(5) 0.9043(4) 0.29408(16) 0.0817(10) Uani 1 1 d . . . . .
C00R C 0.4549(6) 1.0158(4) 0.30313(17) 0.0894(11) Uani 1 1 d . . . . .
H00R H 0.443972 1.064628 0.270309 0.107 Uiso 1 1 calc R U . . .
C00S C 0.5423(8) 0.2936(3) 0.6421(2) 0.1031(14) Uani 1 1 d . . . . .
H00A H 0.439320 0.253003 0.635700 0.155 Uiso 1 1 calc R U . . .
H00B H 0.595243 0.268437 0.679091 0.155 Uiso 1 1 calc R U . . .
H00C H 0.616985 0.281258 0.608117 0.155 Uiso 1 1 calc R U . . .
C00T C 0.3814(9) 0.8590(6) 0.2320(2) 0.132(2) Uani 1 1 d . . . . .
H00D H 0.475123 0.817421 0.216070 0.198 Uiso 1 1 calc R U . . .
H00G H 0.355569 0.919551 0.204900 0.198 Uiso 1 1 calc R U . . .
H00I H 0.284832 0.811018 0.235534 0.198 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
O001 C00D 1.341(3) . ?
O001 C00F 1.431(3) . ?
O002 C00A 1.362(3) . ?
O002 C00E 1.415(3) . ?
O003 H003 0.8200 . ?
O003 C00G 1.307(4) . ?
O004 C00C 1.195(3) . ?
O005 C00D 1.216(3) . ?
O006 C00A 1.206(3) . ?
O007 H007 0.8200 . ?
O007 C00C 1.314(3) . ?
O008 H00N 0.8497 . ?
O008 H00Q 0.8504 . ?
O009 C00G 1.196(4) . ?
C00A C00B 1.469(4) . ?
C00B C00K 1.398(4) . ?
C00B C00M 1.387(4) . ?
C00C C00E 1.511(4) . ?
C00D C00I 1.467(4) . ?
C00E H00E 0.9800 . ?
C00E C00F 1.509(4) . ?
C00F H00F 0.9800 . ?
C00F C00G 1.515(4) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.392(4) . ?
C00H C00O 1.375(5) . ?
C00I C00P 1.384(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.374(4) . ?
C00J C00N 1.379(5) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00M 1.379(4) . ?
C00L C00N 1.394(5) . ?
C00M H00M 0.9300 . ?
C00N C00S 1.501(5) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.392(5) . ?
C00P H00P 0.9300 . ?
C00P C00R 1.380(6) . ?
C00Q C00R 1.371(6) . ?
C00Q C00T 1.503(6) . ?
C00R H00R 0.9300 . ?
C00S H00A 0.9600 . ?
C00S H00B 0.9600 . ?
C00S H00C 0.9600 . ?
C00T H00D 0.9600 . ?
C00T H00G 0.9600 . ?
C00T H00I 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 C00F 118.22(19) . . ?
C00A O002 C00E 116.9(2) . . ?
C00G O003 H003 109.5 . . ?
C00C O007 H007 109.5 . . ?
H00N O008 H00Q 104.6 . . ?
O002 C00A C00B 111.9(2) . . ?
O006 C00A O002 121.6(3) . . ?
O006 C00A C00B 126.5(3) . . ?
C00K C00B C00A 122.0(2) . . ?
C00M C00B C00A 119.0(2) . . ?
C00M C00B C00K 119.0(3) . . ?
O004 C00C O007 125.6(3) . . ?
O004 C00C C00E 123.2(2) . . ?
O007 C00C C00E 111.2(2) . . ?
O001 C00D C00I 112.2(2) . . ?
O005 C00D O001 121.6(3) . . ?
O005 C00D C00I 126.2(2) . . ?
O002 C00E C00C 110.4(2) . . ?
O002 C00E H00E 109.7 . . ?
O002 C00E C00F 107.08(19) . . ?
C00C C00E H00E 109.7 . . ?
C00F C00E C00C 110.3(2) . . ?
C00F C00E H00E 109.7 . . ?
O001 C00F C00E 106.6(2) . . ?
O001 C00F H00F 108.9 . . ?
O001 C00F C00G 112.1(2) . . ?
C00E C00F H00F 108.9 . . ?
C00E C00F C00G 111.4(2) . . ?
C00G C00F H00F 108.9 . . ?
O003 C00G C00F 112.6(2) . . ?
O009 C00G O003 126.0(3) . . ?
O009 C00G C00F 121.4(3) . . ?
C00I C00H H00H 119.9 . . ?
C00O C00H H00H 119.9 . . ?
C00O C00H C00I 120.1(3) . . ?
C00H C00I C00D 121.3(2) . . ?
C00P C00I C00D 119.4(3) . . ?
C00P C00I C00H 119.3(3) . . ?
C00K C00J H00J 119.0 . . ?
C00K C00J C00N 122.0(3) . . ?
C00N C00J H00J 119.0 . . ?
C00B C00K H00K 120.2 . . ?
C00J C00K C00B 119.6(3) . . ?
C00J C00K H00K 120.2 . . ?
C00M C00L H00L 119.6 . . ?
C00M C00L C00N 120.7(3) . . ?
C00N C00L H00L 119.6 . . ?
C00B C00M H00M 119.8 . . ?
C00L C00M C00B 120.5(3) . . ?
C00L C00M H00M 119.8 . . ?
C00J C00N C00L 118.2(3) . . ?
C00J C00N C00S 120.9(4) . . ?
C00L C00N C00S 120.9(4) . . ?
C00H C00O H00O 119.6 . . ?
C00H C00O C00Q 120.7(3) . . ?
C00Q C00O H00O 119.6 . . ?
C00I C00P H00P 120.1 . . ?
C00R C00P C00I 119.7(3) . . ?
C00R C00P H00P 120.1 . . ?
C00O C00Q C00T 120.0(4) . . ?
C00R C00Q C00O 118.5(3) . . ?
C00R C00Q C00T 121.5(4) . . ?
C00P C00R H00R 119.2 . . ?
C00Q C00R C00P 121.6(3) . . ?
C00Q C00R H00R 119.2 . . ?
C00N C00S H00A 109.5 . . ?
C00N C00S H00B 109.5 . . ?
C00N C00S H00C 109.5 . . ?
H00A C00S H00B 109.5 . . ?
H00A C00S H00C 109.5 . . ?
H00B C00S H00C 109.5 . . ?
C00Q C00T H00D 109.5 . . ?
C00Q C00T H00G 109.5 . . ?
C00Q C00T H00I 109.5 . . ?
H00D C00T H00G 109.5 . . ?
H00D C00T H00I 109.5 . . ?
H00G C00T H00I 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
O001 C00D C00I C00H -16.1(4) . . . . ?
O001 C00D C00I C00P 163.9(3) . . . . ?
O001 C00F C00G O003 10.3(3) . . . . ?
O001 C00F C00G O009 -170.5(3) . . . . ?
O002 C00A C00B C00K -4.7(4) . . . . ?
O002 C00A C00B C00M 175.0(2) . . . . ?
O002 C00E C00F O001 67.1(2) . . . . ?
O002 C00E C00F C00G -55.5(3) . . . . ?
O004 C00C C00E O002 7.2(4) . . . . ?
O004 C00C C00E C00F 125.3(3) . . . . ?
O005 C00D C00I C00H 165.1(3) . . . . ?
O005 C00D C00I C00P -14.8(4) . . . . ?
O006 C00A C00B C00K 176.1(3) . . . . ?
O006 C00A C00B C00M -4.2(4) . . . . ?
O007 C00C C00E O002 -171.7(2) . . . . ?
O007 C00C C00E C00F -53.5(3) . . . . ?
C00A O002 C00E C00C -83.6(3) . . . . ?
C00A O002 C00E C00F 156.3(2) . . . . ?
C00A C00B C00K C00J -180.0(3) . . . . ?
C00A C00B C00M C00L -179.6(3) . . . . ?
C00C C00E C00F O001 -53.0(3) . . . . ?
C00C C00E C00F C00G -175.6(2) . . . . ?
C00D O001 C00F C00E 146.7(2) . . . . ?
C00D O001 C00F C00G -91.1(3) . . . . ?
C00D C00I C00P C00R -178.4(3) . . . . ?
C00E O002 C00A O006 0.3(4) . . . . ?
C00E O002 C00A C00B -179.0(2) . . . . ?
C00E C00F C00G O003 129.7(3) . . . . ?
C00E C00F C00G O009 -51.1(4) . . . . ?
C00F O001 C00D O005 -0.5(3) . . . . ?
C00F O001 C00D C00I -179.3(2) . . . . ?
C00H C00I C00P C00R 1.6(5) . . . . ?
C00H C00O C00Q C00R 0.0(6) . . . . ?
C00H C00O C00Q C00T 179.5(5) . . . . ?
C00I C00H C00O C00Q -0.1(5) . . . . ?
C00I C00P C00R C00Q -1.7(6) . . . . ?
C00K C00B C00M C00L 0.1(5) . . . . ?
C00K C00J C00N C00L 1.1(5) . . . . ?
C00K C00J C00N C00S 179.9(4) . . . . ?
C00M C00B C00K C00J 0.3(5) . . . . ?
C00M C00L C00N C00J -0.7(5) . . . . ?
C00M C00L C00N C00S -179.5(4) . . . . ?
C00N C00J C00K C00B -0.9(5) . . . . ?
C00N C00L C00M C00B 0.1(5) . . . . ?
C00O C00H C00I C00D 179.3(3) . . . . ?
C00O C00H C00I C00P -0.7(5) . . . . ?
C00O C00Q C00R C00P 0.9(6) . . . . ?
C00T C00Q C00R C00P -178.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_test1
_audit_block_doi                 10.5517/ccdc.csd.cc2jzkhl
_database_code_depnum_ccdc_archive 'CCDC 2353070'
loop_
_audit_author_name
_audit_author_address
Xia
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2024-05-04 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2024-01-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 O8, H2 O'
_chemical_formula_sum            'C20 H20 O9'
_chemical_formula_weight         404.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.9208(2)
_cell_length_b                   11.9910(2)
_cell_length_c                   21.8333(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2073.69(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7890
_cell_measurement_temperature    296
_cell_measurement_theta_max      99
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       clear_block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11693
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.581
_diffrn_reflns_theta_min         4.050
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                3605
_reflns_number_total             4001
_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 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0751P)²+0.0364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1108
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
C20 \\sim C4: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
3.a Free rotating group:
 O25(H25A,H25B)
3.b Ternary CH refined with riding coordinates:
 C26(H26), C7(H7)
3.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C14(H14), C8(H8), C10(H10), C18(H18), C12(H12), C9(H9), C6(H6)
3.d Fitted hexagon refined as free rotating group:
 C16(C18,C12,C15,C9,C6)
3.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C1(H1A,H1B,H1C)
3.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O29(H29)
;
_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
O21 O 0.5502(2) 0.17760(12) 0.38550(7) 0.0519(4) Uani 1 1 d . . . . .
O19 O 0.47935(18) 0.04107(11) 0.48494(7) 0.0495(3) Uani 1 1 d . . . . .
O3 O 0.1759(2) 0.07620(16) 0.44829(9) 0.0675(4) Uani 1 1 d . . . . .
H3 H 0.079612 0.087738 0.436009 0.101 Uiso 1 1 calc R U . . .
O27 O 0.6845(3) 0.19518(15) 0.29580(9) 0.0732(5) Uani 1 1 d . . . . .
O23 O 0.3859(3) -0.12327(13) 0.51981(9) 0.0691(5) Uani 1 1 d . . . . .
O13 O 0.8554(2) 0.10360(15) 0.42052(10) 0.0730(5) Uani 1 1 d . . . . .
O29 O 0.7735(2) -0.07450(13) 0.41427(10) 0.0711(5) Uani 1 1 d . . . . .
H29 H 0.867770 -0.087230 0.428140 0.107 Uiso 1 1 calc R U . . .
O25 O 1.0436(3) -0.16773(14) 0.45745(13) 0.0839(6) Uani 1 1 d G . . . .
H25A H 1.121406 -0.147762 0.481932 0.126 Uiso 1 1 d G U . . .
H25B H 1.022550 -0.234913 0.467361 0.126 Uiso 1 1 d G U . . .
O5 O 0.2255(3) 0.0320(2) 0.35089(10) 0.0917(7) Uani 1 1 d . . . . .
C11 C 0.6110(3) 0.23782(18) 0.33770(10) 0.0511(5) Uani 1 1 d . . . . .
C22 C 0.5697(3) 0.35737(18) 0.34423(10) 0.0510(5) Uani 1 1 d . . . . .
C26 C 0.4450(3) 0.00738(16) 0.42357(10) 0.0495(5) Uani 1 1 d . . . . .
H26 H 0.455986 -0.073872 0.420807 0.059 Uiso 1 1 calc R U . . .
C2 C 0.7531(3) 0.03356(18) 0.40817(11) 0.0520(5) Uani 1 1 d . . . . .
C28 C 0.4449(3) -0.03089(16) 0.53055(10) 0.0518(5) Uani 1 1 d . . . . .
C7 C 0.5791(3) 0.06066(16) 0.38389(10) 0.0493(5) Uani 1 1 d . . . . .
H7 H 0.568379 0.033510 0.341737 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2692(3) 0.0404(2) 0.40292(11) 0.0558(5) Uani 1 1 d . . . . .
C24 C 0.4923(4) 0.3998(2) 0.39606(12) 0.0621(6) Uani 1 1 d . . . . .
H24 H 0.464488 0.352629 0.428320 0.075 Uiso 1 1 calc R U . . .
C14 C 0.6116(4) 0.4290(2) 0.29677(12) 0.0618(6) Uani 1 1 d . . . . .
H14 H 0.664969 0.401579 0.261951 0.074 Uiso 1 1 calc R U . . .
C8 C 0.4564(4) 0.5124(2) 0.39981(13) 0.0711(7) Uani 1 1 d . . . . .
H8 H 0.404570 0.540308 0.434833 0.085 Uiso 1 1 calc R U . . .
C4 C 0.4959(4) 0.5841(2) 0.35260(15) 0.0726(7) Uani 1 1 d . U . . .
C10 C 0.5741(4) 0.5412(2) 0.30122(14) 0.0707(7) Uani 1 1 d . . . . .
H10 H 0.601884 0.588650 0.269075 0.085 Uiso 1 1 calc R U . . .
C16 C 0.5739(3) 0.09571(17) 0.70567(6) 0.0813(8) Uani 1 1 d G . . . .
C18 C 0.5445(3) -0.01761(16) 0.69756(7) 0.0907(9) Uani 1 1 d G . . . .
H18 H 0.553778 -0.066174 0.730598 0.109 Uiso 1 1 calc R U . . .
C12 C 0.5012(3) -0.05836(11) 0.64006(8) 0.0744(7) Uani 1 1 d G . . . .
H12 H 0.481479 -0.134175 0.634638 0.089 Uiso 1 1 calc R U . . .
C15 C 0.4873(2) 0.01422(12) 0.59068(6) 0.0533(5) Uani 1 1 d G . . . .
C9 C 0.5167(2) 0.12754(11) 0.59879(6) 0.0638(6) Uani 1 1 d G . . . .
H9 H 0.507416 0.176102 0.565744 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5600(3) 0.16829(12) 0.65628(8) 0.0753(7) Uani 1 1 d G . . . .
H6 H 0.579715 0.244106 0.661704 0.090 Uiso 1 1 calc R U . . .
C20 C 0.4565(5) 0.7067(2) 0.35785(18) 0.0918(8) Uani 1 1 d . U . . .
H20A H 0.385608 0.719164 0.392843 0.138 Uiso 1 1 calc R U . . .
H20B H 0.399169 0.731173 0.321514 0.138 Uiso 1 1 calc R U . . .
H20C H 0.559662 0.747876 0.362518 0.138 Uiso 1 1 calc R U . . .
C1 C 0.6194(8) 0.1418(5) 0.76763(17) 0.1311(17) Uani 1 1 d . . . . .
H1A H 0.622657 0.221795 0.765670 0.197 Uiso 1 1 calc R U . . .
H1B H 0.728277 0.114188 0.779621 0.197 Uiso 1 1 calc R U . . .
H1C H 0.536450 0.118965 0.797102 0.197 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
O21 C11 1.357(3) . ?
O21 C7 1.421(2) . ?
O19 C26 1.426(3) . ?
O19 C28 1.346(3) . ?
O3 H3 0.8200 . ?
O3 C17 1.309(3) . ?
O27 C11 1.199(3) . ?
O23 C28 1.225(3) . ?
O13 C2 1.198(3) . ?
O29 H29 0.8200 . ?
O29 C2 1.313(3) . ?
O25 H25A 0.8500 . ?
O25 H25B 0.8507 . ?
O5 C17 1.192(3) . ?
C11 C22 1.477(3) . ?
C22 C24 1.384(3) . ?
C22 C14 1.386(3) . ?
C26 H26 0.9800 . ?
C26 C7 1.512(3) . ?
C26 C17 1.516(3) . ?
C2 C7 1.512(3) . ?
C28 C15 1.459(3) . ?
C7 H7 0.9800 . ?
C24 H24 0.9300 . ?
C24 C8 1.382(4) . ?
C14 H14 0.9300 . ?
C14 C10 1.381(4) . ?
C8 H8 0.9300 . ?
C8 C4 1.378(4) . ?
C4 C10 1.380(4) . ?
C4 C20 1.508(4) . ?
C10 H10 0.9300 . ?
C16 C18 1.3900 . ?
C16 C6 1.3900 . ?
C16 C1 1.505(4) . ?
C18 H18 0.9300 . ?
C18 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C15 1.3900 . ?
C15 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C6 1.3900 . ?
C6 H6 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C11 O21 C7 116.66(17) . . ?
C28 O19 C26 118.37(15) . . ?
C17 O3 H3 109.5 . . ?
C2 O29 H29 109.5 . . ?
H25A O25 H25B 104.4 . . ?
O21 C11 C22 111.33(18) . . ?
O27 C11 O21 122.1(2) . . ?
O27 C11 C22 126.5(2) . . ?
C24 C22 C11 122.3(2) . . ?
C24 C22 C14 119.3(2) . . ?
C14 C22 C11 118.5(2) . . ?
O19 C26 H26 108.8 . . ?
O19 C26 C7 106.54(17) . . ?
O19 C26 C17 112.37(18) . . ?
C7 C26 H26 108.8 . . ?
C7 C26 C17 111.37(18) . . ?
C17 C26 H26 108.8 . . ?
O13 C2 O29 125.9(2) . . ?
O13 C2 C7 123.0(2) . . ?
O29 C2 C7 111.1(2) . . ?
O19 C28 C15 112.42(16) . . ?
O23 C28 O19 121.0(2) . . ?
O23 C28 C15 126.54(19) . . ?
O21 C7 C26 106.83(16) . . ?
O21 C7 C2 110.51(18) . . ?
O21 C7 H7 109.7 . . ?
C26 C7 C2 110.41(18) . . ?
C26 C7 H7 109.7 . . ?
C2 C7 H7 109.7 . . ?
O3 C17 C26 112.3(2) . . ?
O5 C17 O3 125.8(2) . . ?
O5 C17 C26 121.9(2) . . ?
C22 C24 H24 120.0 . . ?
C8 C24 C22 119.9(2) . . ?
C8 C24 H24 120.0 . . ?
C22 C14 H14 120.0 . . ?
C10 C14 C22 120.0(2) . . ?
C10 C14 H14 120.0 . . ?
C24 C8 H8 119.4 . . ?
C4 C8 C24 121.2(3) . . ?
C4 C8 H8 119.4 . . ?
C8 C4 C10 118.5(2) . . ?
C8 C4 C20 120.3(3) . . ?
C10 C4 C20 121.2(3) . . ?
C14 C10 H10 119.5 . . ?
C4 C10 C14 121.1(2) . . ?
C4 C10 H10 119.5 . . ?
C18 C16 C6 120.0 . . ?
C18 C16 C1 120.9(3) . . ?
C6 C16 C1 119.1(3) . . ?
C16 C18 H18 120.0 . . ?
C12 C18 C16 120.0 . . ?
C12 C18 H18 120.0 . . ?
C18 C12 H12 120.0 . . ?
C18 C12 C15 120.0 . . ?
C15 C12 H12 120.0 . . ?
C12 C15 C28 118.95(12) . . ?
C9 C15 C28 121.04(12) . . ?
C9 C15 C12 120.0 . . ?
C15 C9 H9 120.0 . . ?
C6 C9 C15 120.0 . . ?
C6 C9 H9 120.0 . . ?
C16 C6 H6 120.0 . . ?
C9 C6 C16 120.0 . . ?
C9 C6 H6 120.0 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C1 H1A 109.5 . . ?
C16 C1 H1B 109.5 . . ?
C16 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O21 C11 C22 C24 5.4(3) . . . . ?
O21 C11 C22 C14 -175.1(2) . . . . ?
O19 C26 C7 O21 -67.3(2) . . . . ?
O19 C26 C7 C2 52.9(2) . . . . ?
O19 C26 C17 O3 -10.5(3) . . . . ?
O19 C26 C17 O5 170.3(2) . . . . ?
O19 C28 C15 C12 -163.33(14) . . . . ?
O19 C28 C15 C9 15.5(2) . . . . ?
O27 C11 C22 C24 -176.4(3) . . . . ?
O27 C11 C22 C14 3.2(4) . . . . ?
O23 C28 C15 C12 16.0(3) . . . . ?
O23 C28 C15 C9 -165.2(2) . . . . ?
O13 C2 C7 O21 -7.2(3) . . . . ?
O13 C2 C7 C26 -125.1(2) . . . . ?
O29 C2 C7 O21 171.94(19) . . . . ?
O29 C2 C7 C26 54.0(2) . . . . ?
C11 O21 C7 C26 -156.51(19) . . . . ?
C11 O21 C7 C2 83.4(2) . . . . ?
C11 C22 C24 C8 -179.9(3) . . . . ?
C11 C22 C14 C10 179.6(2) . . . . ?
C22 C24 C8 C4 0.1(5) . . . . ?
C22 C14 C10 C4 0.4(4) . . . . ?
C26 O19 C28 O23 0.2(3) . . . . ?
C26 O19 C28 C15 179.60(17) . . . . ?
C28 O19 C26 C7 -146.33(17) . . . . ?
C28 O19 C26 C17 91.4(2) . . . . ?
C28 C15 C9 C6 -178.78(18) . . . . ?
C7 O21 C11 O27 0.5(3) . . . . ?
C7 O21 C11 C22 178.86(18) . . . . ?
C7 C26 C17 O3 -130.0(2) . . . . ?
C7 C26 C17 O5 50.9(3) . . . . ?
C17 C26 C7 O21 55.6(2) . . . . ?
C17 C26 C7 C2 175.79(18) . . . . ?
C24 C22 C14 C10 -0.8(4) . . . . ?
C24 C8 C4 C10 -0.5(5) . . . . ?
C24 C8 C4 C20 -179.6(3) . . . . ?
C14 C22 C24 C8 0.5(4) . . . . ?
C8 C4 C10 C14 0.2(4) . . . . ?
C16 C18 C12 C15 0.0 . . . . ?
C18 C16 C6 C9 0.0 . . . . ?
C18 C12 C15 C28 178.81(18) . . . . ?
C18 C12 C15 C9 0.0 . . . . ?
C12 C15 C9 C6 0.0 . . . . ?
C15 C9 C6 C16 0.0 . . . . ?
C6 C16 C18 C12 0.0 . . . . ?
C20 C4 C10 C14 179.3(3) . . . . ?
C1 C16 C18 C12 179.4(3) . . . . ?
C1 C16 C6 C9 -179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
