# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2216468'
loop_
_audit_author_name
_audit_author_address
'tong zhou'
;college of chemistry and molecular engineering, Peking University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 O4'
_chemical_formula_weight         130.10

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5342(9)
_cell_length_b                   6.5619(4)
_cell_length_c                   9.7191(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.851(12)
_cell_angle_gamma                90
_cell_volume                     547.20(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    179.99(10)
_cell_measurement_reflns_used    1326
_cell_measurement_theta_min      2.4780
_cell_measurement_theta_max      29.6470

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.55701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      179.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3541
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         29.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1381
_reflns_number_gt                994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0596P)²+0.4400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1381
_refine_ls_number_parameters     101
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_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 0.3969(2) 0.2299(3) 0.1782(3) 0.0655(6) Uani 1 1 d . . . . .
O2 O 0.32693(17) 0.5556(2) 0.16347(17) 0.0368(4) Uani 1 1 d D . . . .
O3A O 0.5970(7) 0.5753(9) 0.4356(6) 0.0534(12) Uani 0.533(4) 1 d D U P A 1
O3B O 0.6278(8) 0.6097(11) 0.3921(7) 0.0534(12) Uani 0.467(4) 1 d D U P A 2
O4A O 0.6391(6) 0.6061(8) 0.2161(6) 0.0468(11) Uani 0.533(4) 1 d D U P A 1
O4B O 0.6035(8) 0.6286(9) 0.1429(7) 0.0468(11) Uani 0.467(4) 1 d D U P A 2
C1 C 0.4332(3) 0.4054(3) 0.2045(3) 0.0426(6) Uani 1 1 d D U . . .
C2A C 0.5998(9) 0.4756(11) 0.3093(7) 0.0398(13) Uani 0.533(4) 1 d D U P A 1
H2A H 0.6708 0.3586 0.3426 0.048 Uiso 0.533(4) 1 calc R U P A 1
C2B C 0.5911(11) 0.5030(13) 0.2538(8) 0.0398(13) Uani 0.467(4) 1 d D U P A 2
H2B H 0.6676 0.3930 0.2763 0.048 Uiso 0.467(4) 1 calc R U P A 2
C3A C 0.5237(10) 0.7673(14) 0.1552(8) 0.0411(14) Uani 0.533(4) 1 d D U P A 1
H3AA H 0.4736 0.7585 0.0445 0.049 Uiso 0.533(4) 1 calc R U P A 1
H3AB H 0.5757 0.8983 0.1829 0.049 Uiso 0.533(4) 1 calc R U P A 1
C3B C 0.4867(12) 0.7869(17) 0.0998(10) 0.0411(14) Uani 0.467(4) 1 d D U P A 2
H3BA H 0.4135 0.7748 -0.0071 0.049 Uiso 0.467(4) 1 calc R U P A 2
H3BB H 0.5345 0.9207 0.1170 0.049 Uiso 0.467(4) 1 calc R U P A 2
C4A C 0.401(2) 0.755(3) 0.2137(18) 0.0324(10) Uani 0.533(4) 1 d D U P A 1
H4A H 0.3266 0.8685 0.1784 0.039 Uiso 0.533(4) 1 calc R U P A 1
C4B C 0.406(3) 0.753(3) 0.202(2) 0.0324(10) Uani 0.467(4) 1 d D U P A 2
H4B H 0.3263 0.8585 0.1776 0.039 Uiso 0.467(4) 1 calc R U P A 2
C5A C 0.4786(9) 0.7335(12) 0.3851(12) 0.0413(15) Uani 0.533(4) 1 d D U P A 1
H5AA H 0.5261 0.8623 0.4307 0.050 Uiso 0.533(4) 1 calc R U P A 1
H5AB H 0.4003 0.7012 0.4203 0.050 Uiso 0.533(4) 1 calc R U P A 1
C5B C 0.5165(11) 0.7723(14) 0.3679(14) 0.0413(15) Uani 0.467(4) 1 d D . P A 2
H5BA H 0.5675 0.9043 0.3896 0.050 Uiso 0.467(4) 1 calc R U P A 2
H5BB H 0.4626 0.7541 0.4317 0.050 Uiso 0.467(4) 1 calc R U P A 2


_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 1.198(3) . ?
O2 C1 1.343(3) . ?
O2 C4A 1.468(14) . ?
O2 C4B 1.463(15) . ?
O3A C2A 1.402(8) . ?
O3A C5A 1.453(9) . ?
O3B C2B 1.418(10) . ?
O3B C5B 1.450(11) . ?
O4A C2A 1.410(6) . ?
O4A C3A 1.454(7) . ?
O4B C2B 1.402(7) . ?
O4B C3B 1.445(10) . ?
C1 C2B 1.509(10) . ?
C1 C2A 1.537(8) . ?
C2A H2A 0.9800 . ?
C2B H2B 0.9800 . ?
C3A C4A 1.509(15) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3B C4B 1.511(15) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4A C5A 1.507(14) . ?
C4A H4A 0.9800 . ?
C4B C5B 1.501(15) . ?
C4B H4B 0.9800 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?

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 C4A 111.4(10) . . ?
C1 O2 C4B 109.6(11) . . ?
C2A O3A C5A 110.3(6) . . ?
C2B O3B C5B 110.5(7) . . ?
C2A O4A C3A 109.8(6) . . ?
C2B O4B C3B 109.5(7) . . ?
O1 C1 O2 122.1(2) . . ?
O1 C1 C2B 129.1(4) . . ?
O2 C1 C2B 107.6(4) . . ?
O1 C1 C2A 123.3(3) . . ?
O2 C1 C2A 113.9(3) . . ?
O3A C2A O4A 113.0(6) . . ?
O3A C2A C1 108.1(6) . . ?
O4A C2A C1 104.1(4) . . ?
O3A C2A H2A 110.5 . . ?
O4A C2A H2A 110.5 . . ?
C1 C2A H2A 110.5 . . ?
O4B C2B O3B 111.7(7) . . ?
O4B C2B C1 114.3(5) . . ?
O3B C2B C1 108.1(6) . . ?
O4B C2B H2B 107.5 . . ?
O3B C2B H2B 107.5 . . ?
C1 C2B H2B 107.5 . . ?
O4A C3A C4A 112.4(11) . . ?
O4A C3A H3AA 109.1 . . ?
C4A C3A H3AA 109.1 . . ?
O4A C3A H3AB 109.1 . . ?
C4A C3A H3AB 109.1 . . ?
H3AA C3A H3AB 107.8 . . ?
O4B C3B C4B 104.6(13) . . ?
O4B C3B H3BA 110.8 . . ?
C4B C3B H3BA 110.8 . . ?
O4B C3B H3BB 110.8 . . ?
C4B C3B H3BB 110.8 . . ?
H3BA C3B H3BB 108.9 . . ?
O2 C4A C3A 105.1(12) . . ?
O2 C4A C5A 102.5(11) . . ?
C3A C4A C5A 109.5(13) . . ?
O2 C4A H4A 113.0 . . ?
C3A C4A H4A 113.0 . . ?
C5A C4A H4A 113.0 . . ?
O2 C4B C5B 113.0(14) . . ?
O2 C4B C3B 108.6(13) . . ?
C5B C4B C3B 112.0(14) . . ?
O2 C4B H4B 107.7 . . ?
C5B C4B H4B 107.7 . . ?
C3B C4B H4B 107.7 . . ?
O3A C5A C4A 112.1(12) . . ?
O3A C5A H5AA 109.2 . . ?
C4A C5A H5AA 109.2 . . ?
O3A C5A H5AB 109.2 . . ?
C4A C5A H5AB 109.2 . . ?
H5AA C5A H5AB 107.9 . . ?
O3B C5B C4B 103.4(13) . . ?
O3B C5B H5BA 111.1 . . ?
C4B C5B H5BA 111.1 . . ?
O3B C5B H5BB 111.1 . . ?
C4B C5B H5BB 111.1 . . ?
H5BA C5B H5BB 109.1 . . ?

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
C4A O2 C1 O1 177.9(6) . . . . ?
C4B O2 C1 O1 -176.3(7) . . . . ?
C4B O2 C1 C2B -7.6(8) . . . . ?
C4A O2 C1 C2A 7.4(7) . . . . ?
C5A O3A C2A O4A 62.3(7) . . . . ?
C5A O3A C2A C1 -52.4(6) . . . . ?
C3A O4A C2A O3A -61.4(8) . . . . ?
C3A O4A C2A C1 55.7(7) . . . . ?
O1 C1 C2A O3A -116.2(5) . . . . ?
O2 C1 C2A O3A 54.2(5) . . . . ?
O1 C1 C2A O4A 123.4(4) . . . . ?
O2 C1 C2A O4A -66.2(5) . . . . ?
C3B O4B C2B O3B -65.5(9) . . . . ?
C3B O4B C2B C1 57.6(9) . . . . ?
C5B O3B C2B O4B 63.7(9) . . . . ?
C5B O3B C2B C1 -62.9(6) . . . . ?
O1 C1 C2B O4B 111.1(6) . . . . ?
O2 C1 C2B O4B -56.6(7) . . . . ?
O1 C1 C2B O3B -123.8(5) . . . . ?
O2 C1 C2B O3B 68.5(5) . . . . ?
C2A O4A C3A C4A 2.6(10) . . . . ?
C2B O4B C3B C4B 2.9(10) . . . . ?
C1 O2 C4A C3A 52.0(12) . . . . ?
C1 O2 C4A C5A -62.5(12) . . . . ?
O4A C3A C4A O2 -60.1(13) . . . . ?
O4A C3A C4A C5A 49.4(13) . . . . ?
C1 O2 C4B C5B -57.1(16) . . . . ?
C1 O2 C4B C3B 67.9(15) . . . . ?
O4B C3B C4B O2 -64.5(16) . . . . ?
O4B C3B C4B C5B 61.0(17) . . . . ?
C2A O3A C5A C4A -4.0(9) . . . . ?
O2 C4A C5A O3A 62.6(13) . . . . ?
C3A C4A C5A O3A -48.6(13) . . . . ?
C2B O3B C5B C4B 0.9(9) . . . . ?
O2 C4B C5B O3B 60.6(17) . . . . ?
C3B C4B C5B O3B -62.4(15) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_3_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2216470'
loop_
_audit_author_name
_audit_author_address
'tong zhou'
;college of chemistry and molecular engineering, Peking University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 O4'
_chemical_formula_weight         144.12

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   6.6336(3)
_cell_length_b                   10.5499(6)
_cell_length_c                   18.8351(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1318.15(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      3.7520
_cell_measurement_theta_max      28.3560

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.53509
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4711
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.757
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1503
_reflns_number_gt                1103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0525P)²+0.4317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1503
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.79548(17) 0.31765(13) 0.41363(7) 0.0499(4) Uani 1 1 d . . . . .
O2 O 0.48302(16) 0.25173(10) 0.43180(7) 0.0385(3) Uani 1 1 d . . . . .
O3 O 0.39306(17) 0.50636(10) 0.40878(7) 0.0417(3) Uani 1 1 d . . . . .
O4 O 0.40706(17) 0.37968(12) 0.30757(6) 0.0444(3) Uani 1 1 d . . . . .
C1 C 0.6669(3) 0.52907(17) 0.32891(10) 0.0458(5) Uani 1 1 d . . . . .
H1A H 0.5945 0.5944 0.3042 0.069 Uiso 1 1 calc R U . . .
H1B H 0.7512 0.4842 0.2960 0.069 Uiso 1 1 calc R U . . .
H1C H 0.7490 0.5665 0.3653 0.069 Uiso 1 1 calc R U . . .
C2 C 0.5201(2) 0.43869(14) 0.36204(8) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.6187(2) 0.33280(15) 0.40438(9) 0.0325(4) Uani 1 1 d . . . . .
C4 C 0.2777(2) 0.29249(16) 0.41542(9) 0.0336(4) Uani 1 1 d . . . . .
H4 H 0.1792 0.2344 0.4365 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2527(3) 0.42329(15) 0.44484(10) 0.0385(4) Uani 1 1 d . . . . .
H5A H 0.1157 0.4525 0.4374 0.046 Uiso 1 1 calc R U . . .
H5B H 0.2797 0.4232 0.4955 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2587(3) 0.29357(19) 0.33615(9) 0.0438(5) Uani 1 1 d . . . . .
H6A H 0.2807 0.2090 0.3175 0.053 Uiso 1 1 calc R U . . .
H6B H 0.1245 0.3208 0.3226 0.053 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
O1 C3 1.1965(19) . ?
O2 C3 1.3446(19) . ?
O2 C4 1.4610(19) . ?
O3 C2 1.4122(18) . ?
O3 C5 1.4477(19) . ?
O4 C2 1.4149(19) . ?
O4 C6 1.443(2) . ?
C1 C2 1.499(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.521(2) . ?
C4 C5 1.496(2) . ?
C4 C6 1.499(2) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
C3 O2 C4 110.82(12) . . ?
C2 O3 C5 111.72(11) . . ?
C2 O4 C6 111.58(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 O4 111.00(12) . . ?
O3 C2 C1 109.00(13) . . ?
O4 C2 C1 108.80(13) . . ?
O3 C2 C3 107.52(12) . . ?
O4 C2 C3 106.55(12) . . ?
C1 C2 C3 113.97(14) . . ?
O1 C3 O2 121.01(15) . . ?
O1 C3 C2 126.59(15) . . ?
O2 C3 C2 112.39(13) . . ?
O2 C4 C5 107.25(13) . . ?
O2 C4 C6 106.92(13) . . ?
C5 C4 C6 110.65(15) . . ?
O2 C4 H4 110.6 . . ?
C5 C4 H4 110.6 . . ?
C6 C4 H4 110.6 . . ?
O3 C5 C4 108.25(13) . . ?
O3 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
O3 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
O4 C6 C4 108.60(13) . . ?
O4 C6 H6A 110.0 . . ?
C4 C6 H6A 110.0 . . ?
O4 C6 H6B 110.0 . . ?
C4 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?

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
C5 O3 C2 O4 62.57(17) . . . . ?
C5 O3 C2 C1 -177.62(14) . . . . ?
C5 O3 C2 C3 -53.61(17) . . . . ?
C6 O4 C2 O3 -58.56(17) . . . . ?
C6 O4 C2 C1 -178.49(15) . . . . ?
C6 O4 C2 C3 58.21(16) . . . . ?
C4 O2 C3 O1 178.04(15) . . . . ?
C4 O2 C3 C2 -2.54(18) . . . . ?
O3 C2 C3 O1 -119.94(18) . . . . ?
O4 C2 C3 O1 120.99(17) . . . . ?
C1 C2 C3 O1 1.0(2) . . . . ?
O3 C2 C3 O2 60.68(16) . . . . ?
O4 C2 C3 O2 -58.39(16) . . . . ?
C1 C2 C3 O2 -178.39(14) . . . . ?
C3 O2 C4 C5 -57.80(17) . . . . ?
C3 O2 C4 C6 60.92(17) . . . . ?
C2 O3 C5 C4 -4.83(19) . . . . ?
O2 C4 C5 O3 62.76(17) . . . . ?
C6 C4 C5 O3 -53.51(18) . . . . ?
C2 O4 C6 C4 -1.57(19) . . . . ?
O2 C4 C6 O4 -59.20(18) . . . . ?
C5 C4 C6 O4 57.29(18) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_3_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2216471'
loop_
_audit_author_name
_audit_author_address
'tong zhou'
;college of chemistry and molecular engineering, Peking University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 O4'
_chemical_formula_sum            'C6 H8 O4'
_chemical_formula_weight         144.12

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.61470(10)
_cell_length_b                   8.8811(2)
_cell_length_c                   11.0758(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     650.66(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(11)
_cell_measurement_reflns_used    6965
_cell_measurement_theta_min      6.3660
_cell_measurement_theta_max      75.3460

_exptl_crystal_description       rod-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(11)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12322
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.388
_diffrn_reflns_theta_max         75.435
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1315
_reflns_number_gt                1278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    1.000

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0296P)²+0.1532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 490 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1315
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0606
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 -0.02620(18) 0.31465(14) 0.32429(14) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.29826(17) 0.26983(12) 0.36426(11) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.30370(19) 0.57902(12) 0.41321(11) 0.0249(3) Uani 1 1 d . . . . .
O4 O 0.35474(18) 0.51473(13) 0.21165(10) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.1447(3) 0.36062(18) 0.33233(15) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.2161(2) 0.52061(17) 0.30802(15) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.1003 0.5830 0.2849 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5219(3) 0.41583(18) 0.24135(15) 0.0224(3) Uani 1 1 d . . . . .
H3A H 0.6483 0.4711 0.2380 0.027 Uiso 1 1 calc R U . . .
H3B H 0.5288 0.3337 0.1837 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4894(2) 0.35446(17) 0.36685(15) 0.0189(3) Uani 1 1 d . . . . .
H4 H 0.6016 0.2885 0.3902 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4631(3) 0.48016(19) 0.45827(15) 0.0230(4) Uani 1 1 d . . . . .
H5 H 0.4196 0.4365 0.5353 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6518(3) 0.5719(2) 0.47914(18) 0.0327(4) Uani 1 1 d . . . . .
H6A H 0.6930 0.6180 0.4047 0.049 Uiso 1 1 calc R U . . .
H6B H 0.7578 0.5075 0.5081 0.049 Uiso 1 1 calc R U . . .
H6C H 0.6247 0.6487 0.5380 0.049 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
O1 C1 1.205(2) . ?
O2 C1 1.344(2) . ?
O2 C4 1.4712(19) . ?
O3 C2 1.401(2) . ?
O3 C5 1.460(2) . ?
O4 C2 1.408(2) . ?
O4 C3 1.450(2) . ?
C1 C2 1.521(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.508(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.508(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
C1 O2 C4 110.36(11) . . ?
C2 O3 C5 111.11(12) . . ?
C2 O4 C3 110.31(12) . . ?
O1 C1 O2 121.67(15) . . ?
O1 C1 C2 126.47(16) . . ?
O2 C1 C2 111.86(13) . . ?
O3 C2 O4 112.02(13) . . ?
O3 C2 C1 109.09(13) . . ?
O4 C2 C1 107.56(12) . . ?
O3 C2 H2 109.4 . . ?
O4 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
O4 C3 C4 108.61(13) . . ?
O4 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
O4 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
O2 C4 C3 106.81(13) . . ?
O2 C4 C5 106.88(13) . . ?
C3 C4 C5 111.44(13) . . ?
O2 C4 H4 110.5 . . ?
C3 C4 H4 110.5 . . ?
C5 C4 H4 110.5 . . ?
O3 C5 C6 108.96(14) . . ?
O3 C5 C4 107.28(13) . . ?
C6 C5 C4 113.90(15) . . ?
O3 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C4 O2 C1 O1 179.92(16) . . . . ?
C4 O2 C1 C2 0.49(18) . . . . ?
C5 O3 C2 O4 -64.78(16) . . . . ?
C5 O3 C2 C1 54.19(17) . . . . ?
C3 O4 C2 O3 61.87(15) . . . . ?
C3 O4 C2 C1 -58.00(16) . . . . ?
O1 C1 C2 O3 120.04(19) . . . . ?
O2 C1 C2 O3 -60.57(17) . . . . ?
O1 C1 C2 O4 -118.25(19) . . . . ?
O2 C1 C2 O4 61.14(17) . . . . ?
C2 O4 C3 C4 -0.55(17) . . . . ?
C1 O2 C4 C3 -59.75(16) . . . . ?
C1 O2 C4 C5 59.64(16) . . . . ?
O4 C3 C4 O2 60.79(14) . . . . ?
O4 C3 C4 C5 -55.61(17) . . . . ?
C2 O3 C5 C6 128.79(15) . . . . ?
C2 O3 C5 C4 5.04(18) . . . . ?
O2 C4 C5 O3 -63.59(15) . . . . ?
C3 C4 C5 O3 52.76(18) . . . . ?
O2 C4 C5 C6 175.74(13) . . . . ?
C3 C4 C5 C6 -67.91(18) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_tx5187
_database_code_depnum_ccdc_archive 'CCDC 2216477'
loop_
_audit_author_name
_audit_author_address
'tong zhou'
;college of chemistry and molecular engineering, Peking University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 O5'
_chemical_formula_sum            'C12 H14 O5'
_chemical_formula_weight         238.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
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                   11.18050(10)
_cell_length_b                   9.24640(10)
_cell_length_c                   11.14820(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.8010(10)
_cell_angle_gamma                90
_cell_volume                     1108.945(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12736
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.0360
_cell_measurement_theta_min      4.0890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14573
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.201
_diffrn_reflns_theta_min         4.109
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -36.00   0.50    0.05    --  -47.32 -40.00-159.00  122
  2  ω    -40.00  22.00   0.50    0.05    --  -47.32  40.00  -6.00  124
  3  ω     36.00 120.00   0.50    0.05    --   47.32  40.00  -6.00  168
  4  ω    -19.00  34.00   0.50    0.05    --   47.32 -40.00-159.00  106
  5  ω   -151.00-126.00   0.50    0.15    --  -99.00 -40.00-159.00   50
  6  ω     90.00 158.00   0.50    0.15    --  103.25  40.00  -6.00  136
  7  ω    -23.00  20.00   0.50    0.05    --  -47.32  19.00 150.00   86
  8  ω    -71.00 -25.00   0.50    0.05    --  -47.32 -77.00  60.00   92
  9  ω     59.00  86.00   0.50    0.05    --   47.32  38.00  60.00   54
 10  ω     27.00  77.00   0.50    0.05    --   47.32  77.00  60.00  100
 11  ω   -121.00 -85.00   0.50    0.15    --  -99.00 -94.00 -60.00   72
 12  ω   -167.00-136.00   0.50    0.15    --  -99.00 -30.00 150.00   62
 13  ω   -104.00 -79.00   0.50    0.15    --  -99.00 -71.00 109.87   50
 14  ω    -62.00 -28.00   0.50    0.15    --  -99.00  61.00 120.00   68
 15  ω   -118.00 -86.00   0.50    0.15    --  -99.00 -46.00 138.90   64
 16  ω   -168.00-139.00   0.50    0.15    --  -99.00 -67.00 122.82   58
 17  ω   -128.00 -82.00   0.50    0.15    --  -99.00 -67.00 122.82   92
 18  ω    -60.00 -30.00   0.50    0.15    --  -99.00  61.00 150.00   60
 19  ω   -158.00 -82.00   0.50    0.15    --  -99.00 -65.00  55.12  152
 20  ω   -119.00 -94.00   0.50    0.15    --  -99.00 -30.00 150.00   50
 21  ω   -105.00 -79.00   0.50    0.15    --  -99.00 -69.00  92.22   52
 22  ω   -110.00 -80.00   0.50    0.15    --  -99.00 -68.00  81.05   60
 23  ω   -159.00-127.00   0.50    0.15    --  -99.00 -94.00 -60.00   64
 24  ω   -162.00-121.00   0.50    0.15    --  -99.00 -48.00  94.94   82
 25  ω   -142.00 -83.00   0.50    0.15    --  -99.00 -61.00  60.00  118
 26  ω   -107.00 -81.00   0.50    0.15    --  -99.00 -73.00 101.88   52
 27  ω   -157.00-131.00   0.50    0.15    --  -99.00 -30.00 -90.00   52
 28  ω    -65.00 -27.00   0.50    0.15    --  -99.00  61.00  30.00   76
 29  ω   -160.00-122.00   0.50    0.15    --  -99.00 -77.00 150.00   76
 30  ω   -103.00 -77.00   0.50    0.15    --  -99.00 -77.00 150.00   52
 31  ω    -66.00 -33.00   0.50    0.15    --  -99.00  61.00   0.00   66
 32  ω   -132.00 -86.00   0.50    0.15    --  -99.00 -45.00 120.00   92
 33  ω   -102.00 -76.00   0.50    0.15    --  -99.00 -77.00  85.35   52
 34  ω   -164.00 -85.00   0.50    0.15    --  -99.00 -48.00  86.00  158
 35  ω   -166.00 -76.00   0.50    0.15    --  -99.00 -76.00 -55.27  180
 36  ω   -105.00 -80.00   0.50    0.15    --  -99.00 -68.00 130.38   50
 37  ω    -63.00 -36.00   0.50    0.15    --  -99.00  61.00-150.00   54
 38  ω    -61.00 -29.00   0.50    0.15    --  -99.00  61.00-180.00   64
 39  ω    -67.00 -27.00   0.50    0.15    --  -99.00  61.00-120.00   80
 40  ω   -116.00 -86.00   0.50    0.15    --  -99.00 -48.00  94.94   60
 41  ω   -107.00 -81.00   0.50    0.15    --  -99.00 -66.00 114.45   52
 42  ω     48.00 104.00   0.50    0.15    --  103.25 -94.00  60.00  112
 43  ω     44.00  74.00   0.50    0.15    --  103.25 -61.00 150.00   60
 44  ω     31.00  75.00   0.50    0.15    --  103.25 -61.00-150.00   88
 45  ω    140.00 166.00   0.50    0.15    --  103.25 125.00-120.00   52
 46  ω     80.00 124.00   0.50    0.15    --  103.25 125.00-120.00   88
 47  ω     31.00  65.00   0.50    0.15    --  103.25 -61.00 -90.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0307742000
_diffrn_orient_matrix_UB_12      0.0110427000
_diffrn_orient_matrix_UB_13      -0.1430630000
_diffrn_orient_matrix_UB_21      0.1194605000
_diffrn_orient_matrix_UB_22      -0.0844175000
_diffrn_orient_matrix_UB_23      0.0024424000
_diffrn_orient_matrix_UB_31      -0.0727056000
_diffrn_orient_matrix_UB_32      -0.1432214000
_diffrn_orient_matrix_UB_33      -0.0125016000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2154
_reflns_number_total             2202
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0336
_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)+(0.0431P)²+0.3639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5A), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 0.29837(7) 0.39523(8) 0.67296(7) 0.02303(19) Uani 1 1 d . . . . .
O2 O 0.49025(7) 0.49149(9) 0.72993(7) 0.0261(2) Uani 1 1 d . . . . .
O3 O 0.25072(7) 0.67732(8) 0.57843(7) 0.02387(19) Uani 1 1 d . . . . .
O4 O 0.43767(7) 0.65976(8) 0.52599(7) 0.02168(19) Uani 1 1 d . . . . .
O5 O 0.34709(8) 0.96494(8) 0.52098(8) 0.0272(2) Uani 1 1 d . . . . .
H5 H 0.389134 0.928844 0.586015 0.041 Uiso 1 1 calc R U . . .
C1 C 0.22258(10) 0.21360(11) 0.78828(10) 0.0199(2) Uani 1 1 d . . . . .
C2 C 0.17139(11) 0.24282(12) 0.88597(11) 0.0253(2) Uani 1 1 d . . . . .
H2 H 0.205735 0.314916 0.943152 0.030 Uiso 1 1 calc R U . . .
C3 C 0.06921(11) 0.16522(14) 0.89907(12) 0.0319(3) Uani 1 1 d . . . . .
H3 H 0.036359 0.184593 0.965564 0.038 Uiso 1 1 calc R U . . .
C4 C 0.01635(11) 0.05944(15) 0.81360(13) 0.0336(3) Uani 1 1 d . . . . .
H4 H -0.053019 0.008813 0.821393 0.040 Uiso 1 1 calc R U . . .
C5 C 0.06725(13) 0.02926(14) 0.71634(12) 0.0352(3) Uani 1 1 d . . . . .
H5A H 0.031959 -0.042021 0.658704 0.042 Uiso 1 1 calc R U . . .
C6 C 0.17061(12) 0.10464(13) 0.70420(11) 0.0282(3) Uani 1 1 d . . . . .
H6 H 0.205293 0.082227 0.639560 0.034 Uiso 1 1 calc R U . . .
C7 C 0.33582(10) 0.29418(12) 0.77837(10) 0.0220(2) Uani 1 1 d . . . . .
H7A H 0.371941 0.346939 0.854877 0.026 Uiso 1 1 calc R U . . .
H7B H 0.397468 0.226939 0.764849 0.026 Uiso 1 1 calc R U . . .
C8 C 0.38681(10) 0.48594(11) 0.66123(9) 0.0187(2) Uani 1 1 d . . . . .
C9 C 0.33768(9) 0.58361(11) 0.54805(10) 0.0194(2) Uani 1 1 d . . . . .
H9 H 0.296964 0.525310 0.474921 0.023 Uiso 1 1 calc R U . . .
C10 C 0.19594(10) 0.76925(12) 0.47369(11) 0.0260(3) Uani 1 1 d . . . . .
H10A H 0.138726 0.836231 0.495951 0.031 Uiso 1 1 calc R U . . .
H10B H 0.149295 0.710761 0.404459 0.031 Uiso 1 1 calc R U . . .
C11 C 0.29583(10) 0.85345(12) 0.43437(10) 0.0225(2) Uani 1 1 d . . . . .
H11 H 0.257130 0.898835 0.353688 0.027 Uiso 1 1 calc R U . . .
C12 C 0.39445(11) 0.74907(12) 0.41678(10) 0.0253(2) Uani 1 1 d . . . . .
H12A H 0.360008 0.688504 0.344585 0.030 Uiso 1 1 calc R U . . .
H12B H 0.463645 0.802871 0.402198 0.030 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
O1 C7 1.4701(12) . ?
O1 C8 1.3300(13) . ?
O2 C8 1.2018(13) . ?
O3 C9 1.4107(13) . ?
O3 C10 1.4393(13) . ?
O4 C9 1.3985(12) . ?
O4 C12 1.4413(13) . ?
O5 H5 0.8200 . ?
O5 C11 1.4219(13) . ?
C1 C2 1.3880(15) . ?
C1 C6 1.3908(16) . ?
C1 C7 1.4988(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.3899(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 H5A 0.9300 . ?
C5 C6 1.3873(17) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5270(14) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5206(15) . ?
C11 H11 0.9800 . ?
C11 C12 1.5177(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C8 O1 C7 114.95(8) . . ?
C9 O3 C10 109.68(8) . . ?
C9 O4 C12 109.68(8) . . ?
C11 O5 H5 109.5 . . ?
C2 C1 C6 118.94(10) . . ?
C2 C1 C7 119.88(10) . . ?
C6 C1 C7 121.12(10) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.55(11) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.18(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.57(11) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5A 119.8 . . ?
C4 C5 C6 120.43(12) . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.30(11) . . ?
C5 C6 H6 119.9 . . ?
O1 C7 C1 108.20(8) . . ?
O1 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C1 C7 H7A 110.1 . . ?
C1 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O1 C8 C9 110.15(8) . . ?
O2 C8 O1 125.21(9) . . ?
O2 C8 C9 124.65(9) . . ?
O3 C9 C8 106.34(8) . . ?
O3 C9 H9 110.1 . . ?
O4 C9 O3 111.67(8) . . ?
O4 C9 C8 108.55(8) . . ?
O4 C9 H9 110.1 . . ?
C8 C9 H9 110.1 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 C11 110.65(9) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
O5 C11 C10 111.55(9) . . ?
O5 C11 H11 108.0 . . ?
O5 C11 C12 112.09(9) . . ?
C10 C11 H11 108.0 . . ?
C12 C11 C10 109.15(9) . . ?
C12 C11 H11 108.0 . . ?
O4 C12 C11 110.09(8) . . ?
O4 C12 H12A 109.6 . . ?
O4 C12 H12B 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.82 2.20 2.8859(11) 140.7 2_656 yes

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
O1 C8 C9 O3 69.69(10) . . . . ?
O1 C8 C9 O4 -170.03(8) . . . . ?
O2 C8 C9 O3 -109.80(11) . . . . ?
O2 C8 C9 O4 10.48(14) . . . . ?
O3 C10 C11 O5 -72.89(11) . . . . ?
O3 C10 C11 C12 51.53(12) . . . . ?
O5 C11 C12 O4 72.07(11) . . . . ?
C1 C2 C3 C4 -0.98(17) . . . . ?
C2 C1 C6 C5 1.66(17) . . . . ?
C2 C1 C7 O1 -108.35(11) . . . . ?
C2 C3 C4 C5 1.28(18) . . . . ?
C3 C4 C5 C6 -0.11(19) . . . . ?
C4 C5 C6 C1 -1.38(19) . . . . ?
C6 C1 C2 C3 -0.49(16) . . . . ?
C6 C1 C7 O1 74.63(12) . . . . ?
C7 O1 C8 O2 -1.29(15) . . . . ?
C7 O1 C8 C9 179.22(8) . . . . ?
C7 C1 C2 C3 -177.57(10) . . . . ?
C7 C1 C6 C5 178.70(11) . . . . ?
C8 O1 C7 C1 172.84(8) . . . . ?
C9 O3 C10 C11 -56.85(11) . . . . ?
C9 O4 C12 C11 58.51(11) . . . . ?
C10 O3 C9 O4 64.23(10) . . . . ?
C10 O3 C9 C8 -177.53(8) . . . . ?
C10 C11 C12 O4 -52.02(12) . . . . ?
C12 O4 C9 O3 -65.14(10) . . . . ?
C12 O4 C9 C8 177.96(8) . . . . ?

_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 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_tx5104
_database_code_depnum_ccdc_archive 'CCDC 2216478'
loop_
_audit_author_name
_audit_author_address
'tong zhou'
;college of chemistry and molecular engineering, Peking University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 O9'
_chemical_formula_sum            'C17 H20 O9'
_chemical_formula_weight         368.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.74180(10)
_cell_length_b                   34.0977(4)
_cell_length_c                   8.47780(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3394.24(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14056
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      74.8840
_cell_measurement_theta_min      2.5770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.008
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19029
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.532
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.08    --   47.20  76.00 -36.00  190
  2  ω    -20.00  61.00   0.50    0.08    --   47.20 -56.00  51.00  162
  3  ω   -168.00 -91.00   0.50    0.20    --  -99.00 -56.00  51.00  154
  4  ω    -99.00 -56.00   0.50    0.20    --  -99.00  93.00  61.00   86
  5  ω     43.00  96.00   0.50    0.20    --  103.25 -76.00-163.00  106
  6  ω   -115.00 -89.00   0.50    0.08    --  -47.20-125.00-180.00   52
  7  ω   -112.00 -71.00   0.50    0.20    --  -99.00 125.00 120.00   82
  8  ω    -67.00 -26.00   0.50    0.20    --  -99.00  61.00 150.00   82
  9  ω    -61.00 -26.00   0.50    0.20    --  -99.00  56.00-165.00   70
 10  ω    -64.00 -38.00   0.50    0.20    --  -99.00  61.00  30.00   52
 11  ω    -55.00 -29.00   0.50    0.20    --  -99.00  61.00 -90.00   52
 12  ω     31.00 111.00   0.50    0.20    --  103.25-125.00   0.00  160
 13  ω     34.00  75.00   0.50    0.20    --  103.25 -61.00  30.00   82
 14  ω     93.00 163.00   0.50    0.20    --  103.25  45.00-120.00  140
 15  ω    138.00 169.00   0.50    0.20    --  103.25  77.00 -90.00   62
 16  ω     83.00 132.00   0.50    0.20    --  103.25  77.00 -90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470376000
_diffrn_orient_matrix_UB_12      -0.0255688000
_diffrn_orient_matrix_UB_13      -0.0416780000
_diffrn_orient_matrix_UB_21      0.0740026000
_diffrn_orient_matrix_UB_22      -0.1490035000
_diffrn_orient_matrix_UB_23      -0.0042526000
_diffrn_orient_matrix_UB_31      -0.0976122000
_diffrn_orient_matrix_UB_32      -0.1007997000
_diffrn_orient_matrix_UB_33      0.0169149000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.565
_reflns_Friedel_fraction_full    0.687
_reflns_Friedel_fraction_max     0.635
_reflns_number_gt                5557
_reflns_number_total             5758
_reflns_odcompleteness_completeness 99.97
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5758
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.027
_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)+(0.0640P)²+0.8559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9A), C11(H11), C14(H14), C16(H16), C9A(H9AB), C11A(H11A), C14A(H14A),
 C16A(H16A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B), C17(H17A,H17B),
 C7A(H7AA,H7AB), C10A(H10C,H10D), C12A(H12C,H12D), C15A(H15C,H15D), C17A(H17C,
 H17D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C2A(H2A), C3A(H3A), C4A(H4A),
 C5A(H5A), C6A(H6A)
2.d Idealised tetrahedral OH refined as rotating group:
 O9(H9), O9A(H9AA)
;
_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 0.34635(15) 0.35959(5) 0.8488(2) 0.0328(4) Uani 1 1 d . . . . .
O2 O 0.2871(3) 0.31511(7) 0.6777(4) 0.0722(9) Uani 1 1 d . . . . .
O3 O 0.47122(12) 0.27839(5) 0.8631(2) 0.0270(3) Uani 1 1 d . . . . .
O4 O 0.28465(12) 0.26386(5) 0.9305(2) 0.0317(4) Uani 1 1 d . . . . .
O5 O 0.41579(14) 0.19377(5) 0.8582(2) 0.0319(4) Uani 1 1 d . . . . .
O6 O 0.5576(2) 0.15362(7) 0.9272(4) 0.0677(8) Uani 1 1 d . . . . .
O7 O 0.42458(14) 0.10163(4) 0.7439(2) 0.0273(4) Uani 1 1 d . . . . .
O8 O 0.36891(14) 0.15730(4) 0.6041(2) 0.0275(3) Uani 1 1 d . . . . .
O9 O 0.21042(15) 0.08996(6) 0.5781(2) 0.0371(4) Uani 1 1 d . . . . .
H9 H 0.159605 0.098149 0.520492 0.056 Uiso 1 1 calc R U . . .
C1 C 0.3397(2) 0.42872(7) 0.7955(3) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.2694(3) 0.44895(10) 0.8976(4) 0.0572(9) Uani 1 1 d . . . . .
H2 H 0.201240 0.437730 0.930535 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2995(5) 0.48547(12) 0.9509(5) 0.0875(17) Uani 1 1 d . . . . .
H3 H 0.251786 0.498803 1.020027 0.105 Uiso 1 1 calc R U . . .
C4 C 0.3997(6) 0.50253(10) 0.9028(5) 0.0839(17) Uani 1 1 d . . . . .
H4 H 0.419446 0.527329 0.939398 0.101 Uiso 1 1 calc R U . . .
C5 C 0.4704(4) 0.48303(10) 0.8010(5) 0.0658(11) Uani 1 1 d . . . . .
H5 H 0.538066 0.494629 0.768056 0.079 Uiso 1 1 calc R U . . .
C6 C 0.4410(2) 0.44585(8) 0.7471(4) 0.0405(6) Uani 1 1 d . . . . .
H6 H 0.489214 0.432493 0.678648 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3082(3) 0.38918(8) 0.7347(4) 0.0429(7) Uani 1 1 d . . . . .
H7A H 0.226295 0.387500 0.720886 0.052 Uiso 1 1 calc R U . . .
H7B H 0.344120 0.384658 0.633324 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3256(2) 0.32332(7) 0.8044(3) 0.0343(6) Uani 1 1 d . . . . .
C9 C 0.36803(18) 0.29314(6) 0.9236(3) 0.0247(5) Uani 1 1 d . . . . .
H9A H 0.379549 0.305157 1.027422 0.030 Uiso 1 1 calc R U . . .
C10 C 0.51653(18) 0.24972(7) 0.9709(3) 0.0290(5) Uani 1 1 d . . . . .
H10A H 0.535686 0.262410 1.069813 0.035 Uiso 1 1 calc R U . . .
H10B H 0.585795 0.238658 0.927236 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4314(2) 0.21706(7) 1.0016(3) 0.0292(5) Uani 1 1 d . . . . .
H11 H 0.458170 0.200313 1.087897 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3165(2) 0.23425(7) 1.0416(3) 0.0336(6) Uani 1 1 d . . . . .
H12A H 0.259695 0.213596 1.041631 0.040 Uiso 1 1 calc R U . . .
H12B H 0.319069 0.245537 1.146607 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4813(2) 0.16284(7) 0.8411(3) 0.0303(5) Uani 1 1 d . . . . .
C14 C 0.45559(19) 0.13962(6) 0.6923(3) 0.0253(5) Uani 1 1 d . . . . .
H14 H 0.524667 0.137881 0.627820 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4061(2) 0.07643(7) 0.6096(3) 0.0317(5) Uani 1 1 d . . . . .
H15A H 0.381582 0.050793 0.645640 0.038 Uiso 1 1 calc R U . . .
H15B H 0.477120 0.073177 0.552532 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3168(2) 0.09344(7) 0.4998(3) 0.0286(5) Uani 1 1 d . . . . .
H16 H 0.314835 0.078113 0.402094 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3484(2) 0.13555(6) 0.4617(3) 0.0278(5) Uani 1 1 d . . . . .
H17A H 0.416314 0.135915 0.396548 0.033 Uiso 1 1 calc R U . . .
H17B H 0.287161 0.147785 0.402847 0.033 Uiso 1 1 calc R U . . .
O1A O 0.15326(15) 0.35582(5) 0.3442(3) 0.0364(4) Uani 1 1 d . . . . .
O2A O 0.29240(15) 0.31461(5) 0.2734(3) 0.0394(4) Uani 1 1 d . . . . .
O3A O 0.20391(12) 0.25733(4) 0.4451(2) 0.0265(3) Uani 1 1 d . . . . .
O4A O 0.03348(12) 0.28333(4) 0.3554(2) 0.0256(3) Uani 1 1 d . . . . .
O5A O 0.04605(13) 0.19707(4) 0.3417(2) 0.0266(3) Uani 1 1 d . . . . .
O6A O 0.0269(2) 0.14155(5) 0.4800(3) 0.0463(5) Uani 1 1 d . . . . .
O7A O 0.09671(15) 0.09941(4) 0.2409(2) 0.0285(4) Uani 1 1 d . . . . .
O8A O 0.13518(14) 0.15719(4) 0.1059(2) 0.0266(3) Uani 1 1 d . . . . .
O9A O 0.29880(16) 0.09160(7) 0.0360(3) 0.0445(5) Uani 1 1 d . . . . .
H9AA H 0.342900 0.096287 -0.036573 0.067 Uiso 1 1 calc R U . . .
C1A C 0.1581(2) 0.42477(7) 0.2903(3) 0.0325(5) Uani 1 1 d . . . . .
C2A C 0.0533(2) 0.43552(9) 0.2314(4) 0.0417(6) Uani 1 1 d . . . . .
H2A H 0.014552 0.418551 0.164349 0.050 Uiso 1 1 calc R U . . .
C3A C 0.0051(3) 0.47102(11) 0.2704(4) 0.0586(9) Uani 1 1 d . . . . .
H3A H -0.065817 0.477767 0.229681 0.070 Uiso 1 1 calc R U . . .
C4A C 0.0603(4) 0.49624(9) 0.3679(5) 0.0660(12) Uani 1 1 d . . . . .
H4A H 0.026671 0.520016 0.394780 0.079 Uiso 1 1 calc R U . . .
C5A C 0.1644(4) 0.48689(10) 0.4264(5) 0.0635(11) Uani 1 1 d . . . . .
H5A H 0.202509 0.504547 0.491186 0.076 Uiso 1 1 calc R U . . .
C6A C 0.2150(3) 0.45065(9) 0.3895(4) 0.0470(7) Uani 1 1 d . . . . .
H6A H 0.285784 0.444072 0.431024 0.056 Uiso 1 1 calc R U . . .
C7A C 0.2103(3) 0.38611(8) 0.2510(4) 0.0472(7) Uani 1 1 d . . . . .
H7AA H 0.201374 0.380667 0.139390 0.057 Uiso 1 1 calc R U . . .
H7AB H 0.291041 0.386490 0.275279 0.057 Uiso 1 1 calc R U . . .
C8A C 0.20388(18) 0.32102(6) 0.3386(3) 0.0264(5) Uani 1 1 d . . . . .
C9A C 0.13679(17) 0.29086(6) 0.4339(3) 0.0227(4) Uani 1 1 d . . . . .
H9AB H 0.121276 0.301180 0.539616 0.027 Uiso 1 1 calc R U . . .
C10A C 0.1509(2) 0.22975(7) 0.5493(3) 0.0286(5) Uani 1 1 d . . . . .
H10C H 0.145056 0.240916 0.654208 0.034 Uiso 1 1 calc R U . . .
H10D H 0.196797 0.206145 0.555793 0.034 Uiso 1 1 calc R U . . .
C11A C 0.03331(19) 0.21973(6) 0.4879(3) 0.0271(5) Uani 1 1 d . . . . .
H11A H -0.008089 0.204209 0.566512 0.033 Uiso 1 1 calc R U . . .
C12A C -0.03248(18) 0.25648(6) 0.4499(3) 0.0289(5) Uani 1 1 d . . . . .
H12C H -0.101426 0.249511 0.393404 0.035 Uiso 1 1 calc R U . . .
H12D H -0.054540 0.269317 0.547288 0.035 Uiso 1 1 calc R U . . .
C13A C 0.04207(18) 0.15866(6) 0.3576(3) 0.0251(4) Uani 1 1 d . . . . .
C14A C 0.05758(18) 0.13714(6) 0.2016(3) 0.0228(4) Uani 1 1 d . . . . .
H14A H -0.015912 0.135144 0.147411 0.027 Uiso 1 1 calc R U . . .
C15A C 0.1074(2) 0.07592(7) 0.1008(3) 0.0345(6) Uani 1 1 d . . . . .
H15C H 0.032686 0.072108 0.054433 0.041 Uiso 1 1 calc R U . . .
H15D H 0.137506 0.050356 0.128734 0.041 Uiso 1 1 calc R U . . .
C16A C 0.1848(2) 0.09490(7) -0.0189(3) 0.0292(5) Uani 1 1 d . . . . .
H16A H 0.177909 0.080837 -0.119228 0.035 Uiso 1 1 calc R U . . .
C17A C 0.1482(2) 0.13720(6) -0.0431(3) 0.0272(5) Uani 1 1 d . . . . .
H17C H 0.204771 0.150711 -0.106438 0.033 Uiso 1 1 calc R U . . .
H17D H 0.076551 0.137783 -0.099940 0.033 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
O1 C7 1.468(3) . ?
O1 C8 1.316(3) . ?
O2 C8 1.198(4) . ?
O3 C9 1.409(3) . ?
O3 C10 1.440(3) . ?
O4 C9 1.399(3) . ?
O4 C12 1.431(3) . ?
O5 C11 1.464(3) . ?
O5 C13 1.314(3) . ?
O6 C13 1.197(3) . ?
O7 C14 1.415(3) . ?
O7 C15 1.443(3) . ?
O8 C14 1.399(3) . ?
O8 C17 1.437(3) . ?
O9 H9 0.8200 . ?
O9 C16 1.419(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.387(4) . ?
C1 C7 1.490(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.527(3) . ?
C9 H9A 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.519(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.510(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.519(3) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.517(3) . ?
C16 H16 0.9800 . ?
C16 C17 1.518(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O1A C7A 1.463(3) . ?
O1A C8A 1.328(3) . ?
O2A C8A 1.198(3) . ?
O3A C9A 1.392(2) . ?
O3A C10A 1.432(3) . ?
O4A C9A 1.407(3) . ?
O4A C12A 1.442(3) . ?
O5A C11A 1.469(3) . ?
O5A C13A 1.318(3) . ?
O6A C13A 1.204(3) . ?
O7A C14A 1.406(3) . ?
O7A C15A 1.438(3) . ?
O8A C14A 1.399(3) . ?
O8A C17A 1.444(3) . ?
O9A H9AA 0.8200 . ?
O9A C16A 1.421(3) . ?
C1A C2A 1.378(4) . ?
C1A C6A 1.390(4) . ?
C1A C7A 1.491(4) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.376(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.358(6) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.357(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.406(5) . ?
C6A H6A 0.9300 . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A C9A 1.527(3) . ?
C9A H9AB 0.9800 . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.515(3) . ?
C11A H11A 0.9800 . ?
C11A C12A 1.507(3) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A C14A 1.523(3) . ?
C14A H14A 0.9800 . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16A 1.508(4) . ?
C16A H16A 0.9800 . ?
C16A C17A 1.519(3) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?

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
C8 O1 C7 113.6(2) . . ?
C9 O3 C10 109.20(17) . . ?
C9 O4 C12 110.35(18) . . ?
C13 O5 C11 116.97(19) . . ?
C14 O7 C15 109.89(18) . . ?
C14 O8 C17 110.38(17) . . ?
C16 O9 H9 109.5 . . ?
C2 C1 C6 119.2(3) . . ?
C2 C1 C7 121.3(3) . . ?
C6 C1 C7 119.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 108.5(2) . . ?
O1 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C1 C7 H7A 110.0 . . ?
C1 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O1 C8 C9 112.5(2) . . ?
O2 C8 O1 123.1(3) . . ?
O2 C8 C9 124.0(2) . . ?
O3 C9 C8 106.3(2) . . ?
O3 C9 H9A 111.0 . . ?
O4 C9 O3 111.24(17) . . ?
O4 C9 C8 106.25(18) . . ?
O4 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
O3 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
O3 C10 C11 111.31(18) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
O5 C11 C10 109.8(2) . . ?
O5 C11 H11 110.1 . . ?
O5 C11 C12 106.58(19) . . ?
C10 C11 H11 110.1 . . ?
C12 C11 C10 109.98(19) . . ?
C12 C11 H11 110.1 . . ?
O4 C12 C11 111.1(2) . . ?
O4 C12 H12A 109.4 . . ?
O4 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O5 C13 C14 113.2(2) . . ?
O6 C13 O5 125.6(2) . . ?
O6 C13 C14 121.2(2) . . ?
O7 C14 C13 105.8(2) . . ?
O7 C14 H14 109.3 . . ?
O8 C14 O7 111.85(18) . . ?
O8 C14 C13 111.34(17) . . ?
O8 C14 H14 109.3 . . ?
C13 C14 H14 109.3 . . ?
O7 C15 H15A 109.4 . . ?
O7 C15 H15B 109.4 . . ?
O7 C15 C16 111.10(18) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
O9 C16 C15 106.8(2) . . ?
O9 C16 H16 109.3 . . ?
O9 C16 C17 113.21(19) . . ?
C15 C16 H16 109.3 . . ?
C15 C16 C17 108.82(19) . . ?
C17 C16 H16 109.3 . . ?
O8 C17 C16 110.5(2) . . ?
O8 C17 H17A 109.5 . . ?
O8 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C8A O1A C7A 113.99(19) . . ?
C9A O3A C10A 109.60(17) . . ?
C9A O4A C12A 108.43(17) . . ?
C13A O5A C11A 115.66(18) . . ?
C14A O7A C15A 110.01(18) . . ?
C14A O8A C17A 110.26(16) . . ?
C16A O9A H9AA 109.5 . . ?
C2A C1A C6A 118.7(3) . . ?
C2A C1A C7A 121.4(3) . . ?
C6A C1A C7A 119.9(3) . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A C1A 121.0(3) . . ?
C3A C2A H2A 119.5 . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.4(3) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A C3A 120.2(3) . . ?
C5A C4A H4A 119.9 . . ?
C4A C5A H5A 119.8 . . ?
C4A C5A C6A 120.4(3) . . ?
C6A C5A H5A 119.8 . . ?
C1A C6A C5A 119.3(3) . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A H6A 120.4 . . ?
O1A C7A C1A 108.4(2) . . ?
O1A C7A H7AA 110.0 . . ?
O1A C7A H7AB 110.0 . . ?
C1A C7A H7AA 110.0 . . ?
C1A C7A H7AB 110.0 . . ?
H7AA C7A H7AB 108.4 . . ?
O1A C8A C9A 110.61(18) . . ?
O2A C8A O1A 124.6(2) . . ?
O2A C8A C9A 124.7(2) . . ?
O3A C9A O4A 111.75(16) . . ?
O3A C9A C8A 107.29(17) . . ?
O3A C9A H9AB 109.7 . . ?
O4A C9A C8A 108.52(19) . . ?
O4A C9A H9AB 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
O3A C10A H10C 109.8 . . ?
O3A C10A H10D 109.8 . . ?
O3A C10A C11A 109.4(2) . . ?
H10C C10A H10D 108.2 . . ?
C11A C10A H10C 109.8 . . ?
C11A C10A H10D 109.8 . . ?
O5A C11A C10A 108.40(18) . . ?
O5A C11A H11A 109.9 . . ?
O5A C11A C12A 108.0(2) . . ?
C10A C11A H11A 109.9 . . ?
C12A C11A C10A 110.70(18) . . ?
C12A C11A H11A 109.9 . . ?
O4A C12A C11A 111.81(18) . . ?
O4A C12A H12C 109.3 . . ?
O4A C12A H12D 109.3 . . ?
C11A C12A H12C 109.3 . . ?
C11A C12A H12D 109.3 . . ?
H12C C12A H12D 107.9 . . ?
O5A C13A C14A 112.7(2) . . ?
O6A C13A O5A 125.1(2) . . ?
O6A C13A C14A 122.18(19) . . ?
O7A C14A C13A 105.90(18) . . ?
O7A C14A H14A 109.6 . . ?
O8A C14A O7A 111.83(17) . . ?
O8A C14A C13A 110.26(17) . . ?
O8A C14A H14A 109.6 . . ?
C13A C14A H14A 109.6 . . ?
O7A C15A H15C 109.3 . . ?
O7A C15A H15D 109.3 . . ?
O7A C15A C16A 111.67(19) . . ?
H15C C15A H15D 107.9 . . ?
C16A C15A H15C 109.3 . . ?
C16A C15A H15D 109.3 . . ?
O9A C16A C15A 108.3(2) . . ?
O9A C16A H16A 108.9 . . ?
O9A C16A C17A 112.7(2) . . ?
C15A C16A H16A 108.9 . . ?
C15A C16A C17A 109.1(2) . . ?
C17A C16A H16A 108.9 . . ?
O8A C17A C16A 111.1(2) . . ?
O8A C17A H17C 109.4 . . ?
O8A C17A H17D 109.4 . . ?
C16A C17A H17C 109.4 . . ?
C16A C17A H17D 109.4 . . ?
H17C C17A H17D 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9 O6A 0.82 2.18 2.903(3) 147.8 . yes
O9A H9AA O7 0.82 2.10 2.904(3) 165.8 1_554 yes

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
O1 C8 C9 O3 -101.3(2) . . . . ?
O1 C8 C9 O4 140.2(2) . . . . ?
O2 C8 C9 O3 72.3(4) . . . . ?
O2 C8 C9 O4 -46.3(4) . . . . ?
O3 C10 C11 O5 68.0(2) . . . . ?
O3 C10 C11 C12 -48.9(3) . . . . ?
O5 C11 C12 O4 -70.4(2) . . . . ?
O5 C13 C14 O7 -120.1(2) . . . . ?
O5 C13 C14 O8 1.6(3) . . . . ?
O6 C13 C14 O7 62.7(3) . . . . ?
O6 C13 C14 O8 -175.6(3) . . . . ?
O7 C15 C16 O9 -71.0(2) . . . . ?
O7 C15 C16 C17 51.6(3) . . . . ?
O9 C16 C17 O8 66.7(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C7 O1 -86.3(3) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C6 C1 C7 O1 94.6(3) . . . . ?
C7 O1 C8 O2 5.4(4) . . . . ?
C7 O1 C8 C9 179.0(2) . . . . ?
C7 C1 C2 C3 -179.3(3) . . . . ?
C7 C1 C6 C5 178.9(3) . . . . ?
C8 O1 C7 C1 -178.1(2) . . . . ?
C9 O3 C10 C11 56.5(2) . . . . ?
C9 O4 C12 C11 -56.5(3) . . . . ?
C10 O3 C9 O4 -65.1(2) . . . . ?
C10 O3 C9 C8 179.70(17) . . . . ?
C10 C11 C12 O4 48.5(3) . . . . ?
C11 O5 C13 O6 -5.3(4) . . . . ?
C11 O5 C13 C14 177.62(19) . . . . ?
C12 O4 C9 O3 65.5(3) . . . . ?
C12 O4 C9 C8 -179.27(19) . . . . ?
C13 O5 C11 C10 92.1(2) . . . . ?
C13 O5 C11 C12 -148.8(2) . . . . ?
C14 O7 C15 C16 -56.5(3) . . . . ?
C14 O8 C17 C16 58.0(2) . . . . ?
C15 O7 C14 O8 62.6(2) . . . . ?
C15 O7 C14 C13 -175.98(18) . . . . ?
C15 C16 C17 O8 -51.9(3) . . . . ?
C17 O8 C14 O7 -63.7(2) . . . . ?
C17 O8 C14 C13 178.21(18) . . . . ?
O1A C8A C9A O3A -170.1(2) . . . . ?
O1A C8A C9A O4A 69.0(2) . . . . ?
O2A C8A C9A O3A 7.0(3) . . . . ?
O2A C8A C9A O4A -113.9(3) . . . . ?
O3A C10A C11A O5A 68.7(2) . . . . ?
O3A C10A C11A C12A -49.5(3) . . . . ?
O5A C11A C12A O4A -69.8(2) . . . . ?
O5A C13A C14A O7A 156.95(17) . . . . ?
O5A C13A C14A O8A 35.8(2) . . . . ?
O6A C13A C14A O7A -23.7(3) . . . . ?
O6A C13A C14A O8A -144.8(2) . . . . ?
O7A C15A C16A O9A 72.9(3) . . . . ?
O7A C15A C16A C17A -50.1(3) . . . . ?
O9A C16A C17A O8A -70.4(3) . . . . ?
C1A C2A C3A C4A 0.1(5) . . . . ?
C2A C1A C6A C5A -0.2(4) . . . . ?
C2A C1A C7A O1A -76.4(4) . . . . ?
C2A C3A C4A C5A 0.8(5) . . . . ?
C3A C4A C5A C6A -1.4(5) . . . . ?
C4A C5A C6A C1A 1.1(5) . . . . ?
C6A C1A C2A C3A -0.4(4) . . . . ?
C6A C1A C7A O1A 102.9(3) . . . . ?
C7A O1A C8A O2A 4.9(4) . . . . ?
C7A O1A C8A C9A -178.0(2) . . . . ?
C7A C1A C2A C3A 178.9(3) . . . . ?
C7A C1A C6A C5A -179.5(3) . . . . ?
C8A O1A C7A C1A -169.9(2) . . . . ?
C9A O3A C10A C11A 58.4(2) . . . . ?
C9A O4A C12A C11A -54.7(2) . . . . ?
C10A O3A C9A O4A -68.1(2) . . . . ?
C10A O3A C9A C8A 173.09(19) . . . . ?
C10A C11A C12A O4A 48.7(3) . . . . ?
C11A O5A C13A O6A 1.5(3) . . . . ?
C11A O5A C13A C14A -179.17(17) . . . . ?
C12A O4A C9A O3A 65.0(2) . . . . ?
C12A O4A C9A C8A -176.90(17) . . . . ?
C13A O5A C11A C10A 95.7(2) . . . . ?
C13A O5A C11A C12A -144.34(18) . . . . ?
C14A O7A C15A C16A 56.5(3) . . . . ?
C14A O8A C17A C16A -56.5(2) . . . . ?
C15A O7A C14A O8A -63.3(2) . . . . ?
C15A O7A C14A C13A 176.52(18) . . . . ?
C15A C16A C17A O8A 49.9(3) . . . . ?
C17A O8A C14A O7A 63.5(2) . . . . ?
C17A O8A C14A C13A -178.92(17) . . . . ?

_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 1.396
_oxdiff_exptl_absorpt_empirical_full_min 0.691
