# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_BPTCA-2
_database_code_depnum_ccdc_archive 'CCDC 2277044'
loop_
_audit_author_name
_audit_author_address
'Peng Cui'
;Jiangsu University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 O8, [+ solvent]'
_chemical_formula_sum            'C16 H10 O8, [+ solvent]'
_chemical_formula_weight         330.24
_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 0.0033 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'

_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           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   15.2243(19)
_cell_length_b                   7.1637(13)
_cell_length_c                   17.5962(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1919.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1911
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      28.4150
_cell_measurement_theta_min      2.3310
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.032
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9436
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.315
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1529
_reflns_number_total             2213
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.

We could not accurately model the disordered solvent in the large 1-D pores and 
used a Solvent Mask in Olex2 during the final refinement crystal. 
Applying the solvent mask described below reduced the wR2(all data) 
from 39.14% to 24.57%.
Void  Vol/Ang^3  #Electrons
   1      351.6         58.2
   2      351.6         58.3 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0919
_refine_ls_restrained_S_all      1.048
_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)+(0.0975P)²+5.1322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2301
_refine_ls_wR_factor_ref         0.2457
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4A), C7(H7)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O3 O 0.53790(13) 0.7119(4) 0.43604(12) 0.0216(6) Uani 1 1 d . . . . .
O2 O 0.53508(13) 0.3017(3) 0.10466(12) 0.0219(6) Uani 1 1 d . . . . .
O1 O 0.60097(14) 0.3761(3) -0.00520(12) 0.0210(6) Uani 1 1 d . . . . .
H1 H 0.559716 0.313536 -0.024045 0.032 Uiso 1 1 calc R U . . .
O4 O 0.60575(14) 0.6437(4) 0.54620(12) 0.0242(6) Uani 1 1 d . . . . .
H4 H 0.562120 0.698154 0.565247 0.036 Uiso 1 1 calc R U . . .
C6 C 0.750000 0.500000 0.3119(2) 0.0152(9) Uani 1 2 d S T P . .
C5 C 0.750000 0.500000 0.2267(2) 0.0140(9) Uani 1 2 d S T P . .
C1 C 0.59694(18) 0.3674(5) 0.06908(18) 0.0167(7) Uani 1 1 d . . . . .
C3 C 0.750000 0.500000 0.0682(3) 0.0161(9) Uani 1 2 d S T P . .
C9 C 0.750000 0.500000 0.4721(2) 0.0144(9) Uani 1 2 d S T P . .
H9 H 0.750001 0.500001 0.526075 0.017 Uiso 1 2 calc R U P . .
C10 C 0.59987(18) 0.6479(5) 0.47177(17) 0.0155(7) Uani 1 1 d . . . . .
C2 C 0.67654(18) 0.4406(4) 0.10839(17) 0.0156(7) Uani 1 1 d . . . . .
C4 C 0.67585(18) 0.4452(4) 0.18776(17) 0.0147(7) Uani 1 1 d . . . . .
H4A H 0.624384 0.410483 0.214825 0.018 Uiso 1 1 calc R U . . .
C8 C 0.67774(18) 0.5663(4) 0.43192(17) 0.0154(7) Uani 1 1 d . . . . .
C7 C 0.67709(18) 0.5632(4) 0.35267(17) 0.0145(7) Uani 1 1 d . . . . .
H7 H 0.626396 0.604535 0.326072 0.017 Uiso 1 1 calc R U . . .
H3 H 0.750000 0.500000 0.023(3) 0.026(15) Uiso 1 2 d S . P . .


_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
O3 C10 1.223(4) . ?
O2 C1 1.225(4) . ?
O1 H1 0.8400 . ?
O1 C1 1.310(4) . ?
O4 H4 0.8400 . ?
O4 C10 1.313(4) . ?
C6 C5 1.499(6) . ?
C6 C7 1.397(4) 2_665 ?
C6 C7 1.397(4) . ?
C5 C4 1.378(4) . ?
C5 C4 1.378(4) 2_665 ?
C1 C2 1.491(4) . ?
C3 C2 1.390(4) . ?
C3 C2 1.390(4) 2_665 ?
C3 H3 0.80(6) . ?
C9 H9 0.9500 . ?
C9 C8 1.391(4) 2_665 ?
C9 C8 1.391(4) . ?
C10 C8 1.496(4) . ?
C2 C4 1.397(4) . ?
C4 H4A 0.9500 . ?
C8 C7 1.395(4) . ?
C7 H7 0.9500 . ?

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 O1 H1 109.5 . . ?
C10 O4 H4 109.5 . . ?
C7 C6 C5 120.9(2) 2_665 . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 C7 118.2(4) 2_665 . ?
C4 C5 C6 119.82(19) . . ?
C4 C5 C6 119.82(19) 2_665 . ?
C4 C5 C4 120.4(4) . 2_665 ?
O2 C1 O1 124.4(3) . . ?
O2 C1 C2 121.5(3) . . ?
O1 C1 C2 114.1(3) . . ?
C2 C3 C2 118.8(4) . 2_665 ?
C2 C3 H3 120.6(2) 2_665 . ?
C2 C3 H3 120.6(2) . . ?
C8 C9 H9 120.5 2_665 . ?
C8 C9 H9 120.5 . . ?
C8 C9 C8 118.9(4) . 2_665 ?
O3 C10 O4 125.0(3) . . ?
O3 C10 C8 121.1(3) . . ?
O4 C10 C8 113.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 C4 120.5(3) . . ?
C4 C2 C1 117.8(3) . . ?
C5 C4 C2 119.8(3) . . ?
C5 C4 H4A 120.1 . . ?
C2 C4 H4A 120.1 . . ?
C9 C8 C10 121.5(3) . . ?
C9 C8 C7 120.5(3) . . ?
C7 C8 C10 118.0(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?

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
O1 H1 O3 0.84 1.80 2.631(3) 171.3 8_655 yes
O4 H4 O2 0.84 1.79 2.634(3) 176.4 8_666 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
O3 C10 C8 C9 177.4(3) . . . . ?
O3 C10 C8 C7 -0.8(5) . . . . ?
O2 C1 C2 C3 174.2(3) . . . . ?
O2 C1 C2 C4 -4.7(5) . . . . ?
O1 C1 C2 C3 -4.2(4) . . . . ?
O1 C1 C2 C4 176.8(3) . . . . ?
O4 C10 C8 C9 -2.3(4) . . . . ?
O4 C10 C8 C7 179.5(3) . . . . ?
C6 C5 C4 C2 -178.4(2) . . . . ?
C5 C6 C7 C8 -178.8(2) . . . . ?
C1 C2 C4 C5 175.7(2) . . . . ?
C3 C2 C4 C5 -3.2(4) . . . . ?
C9 C8 C7 C6 -2.4(4) . . . . ?
C10 C8 C7 C6 175.9(2) . . . . ?
C2 C3 C2 C1 -177.3(3) 2_665 . . . ?
C2 C3 C2 C4 1.6(2) 2_665 . . . ?
C4 C5 C4 C2 1.6(2) 2_665 . . . ?
C8 C9 C8 C10 -177.0(3) 2_665 . . . ?
C8 C9 C8 C7 1.2(2) 2_665 . . . ?
C7 C6 C5 C4 -41.4(2) . . . . ?
C7 C6 C5 C4 138.6(2) . . . 2_665 ?
C7 C6 C5 C4 138.6(2) 2_665 . . . ?
C7 C6 C5 C4 -41.4(2) 2_665 . . 2_665 ?
C7 C6 C7 C8 1.2(2) 2_665 . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.414 0.250 351.6 58.2 ?
2 -0.250 -0.765 0.750 351.6 58.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_BPTCA-2_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2277046'
loop_
_audit_author_name
_audit_author_address
'Peng Cui'
;Jiangsu University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;

_audit_creation_date             2023-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 O8, 0.5(C16 H8 O8), [+ solvent]'
_chemical_formula_sum            'C24 H14 O12, [+ solvent]'
_chemical_formula_weight         494.35
_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 0.0033 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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   10.8266(7)
_cell_length_b                   31.5566(14)
_cell_length_c                   18.5503(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.143(7)
_cell_angle_gamma                90
_cell_volume                     6117.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6259
_cell_measurement_temperature    292.0(5)
_cell_measurement_theta_max      30.5050
_cell_measurement_theta_min      1.7320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.073
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.787
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.708
_diffrn_reflns_theta_min         1.720
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.787
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00  28.00   0.50  101.00    --   -8.90 -68.00 -90.00  252
  2  ω    -96.00 -17.00   0.50  101.00    --   -8.90 -57.00-180.00  158
  3  ω    -30.00   1.00   0.50  101.00    --   -8.90  68.00  60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0396978000
_diffrn_orient_matrix_UB_12      -0.0169497000
_diffrn_orient_matrix_UB_13      0.0174656000
_diffrn_orient_matrix_UB_21      0.0550296000
_diffrn_orient_matrix_UB_22      0.0120156000
_diffrn_orient_matrix_UB_23      -0.0007941000
_diffrn_orient_matrix_UB_31      0.0013579000
_diffrn_orient_matrix_UB_32      0.0085769000
_diffrn_orient_matrix_UB_33      0.0355474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6797
_reflns_number_total             13190
_reflns_special_details          
;
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.

We could not model the disordered, residual solvent in the crystal 
pores and, therefore, used a Solvent Mask in Olex2 during the final 
refinement of the crystal structure. The details about the Solvent 
Mask are shown in the table below.
Void  Vol/Ang^3  #Electrons
   1      596.7        121.9
   2      596.7        121.9
   3      596.7        121.9
   4      596.7        121.9
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       CrysAlisPro
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         13190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      0.964
_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)+(0.1563P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2436
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5263(17)
 0.4737(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6A), C8(H8), C10(H10), C12(H12), C18(H18), C22(H22)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O6(H6), O7(H7), O10(H10A), O11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6506(2) 0.69843(5) 0.51417(8) 0.0591(5) Uani 1 1 d . . . . .
H1 H 0.592884 0.715367 0.497242 0.089 Uiso 1 1 calc R U . . .
O2 O 0.6607(2) 0.73114(4) 0.62199(8) 0.0595(5) Uani 1 1 d . . . . .
O3 O 0.7789(2) 0.54946(5) 0.51557(8) 0.0564(5) Uani 1 1 d . . . . .
H3 H 0.802419 0.528081 0.497814 0.085 Uiso 1 1 calc R U . . .
O4 O 0.88099(19) 0.51870(4) 0.62253(8) 0.0599(5) Uani 1 1 d . . . . .
O5 O 0.8219(2) 0.52060(4) 0.94986(8) 0.0618(6) Uani 1 1 d . . . . .
O6 O 0.9217(2) 0.55196(5) 1.05640(8) 0.0657(6) Uani 1 1 d . . . . .
H6 H 0.900171 0.530287 1.074294 0.099 Uiso 1 1 calc R U . . .
O7 O 1.0553(2) 0.70011(5) 1.05397(8) 0.0697(6) Uani 1 1 d . . . . .
H7 H 1.087286 0.722805 1.070656 0.104 Uiso 1 1 calc R U . . .
O8 O 1.0449(2) 0.73229(4) 0.94574(8) 0.0604(6) Uani 1 1 d . . . . .
C1 C 0.7392(2) 0.66111(5) 0.62608(10) 0.0317(5) Uani 1 1 d . . . . .
C2 C 0.7511(2) 0.62442(6) 0.58681(10) 0.0332(4) Uani 1 1 d . . . . .
H2 H 0.723963 0.623918 0.534930 0.040 Uiso 1 1 calc R U . . .
C3 C 0.8043(2) 0.58851(5) 0.62643(10) 0.0327(5) Uani 1 1 d . . . . .
C4 C 0.8417(2) 0.58902(5) 0.70391(10) 0.0312(5) Uani 1 1 d . . . . .
H4 H 0.874845 0.564527 0.729689 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8304(2) 0.62579(5) 0.74389(9) 0.0295(4) Uani 1 1 d . . . . .
C6 C 0.7790(2) 0.66172(5) 0.70332(10) 0.0310(4) Uani 1 1 d . . . . .
H6A H 0.771294 0.686601 0.728655 0.037 Uiso 1 1 calc R U . . .
C7 C 0.8730(2) 0.62622(5) 0.82631(9) 0.0287(4) Uani 1 1 d . . . . .
C8 C 0.8582(2) 0.59028(5) 0.86765(10) 0.0325(5) Uani 1 1 d . . . . .
H8 H 0.821093 0.566012 0.842719 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8977(2) 0.59024(5) 0.94470(10) 0.0327(5) Uani 1 1 d . . . . .
C10 C 0.9522(2) 0.62625(6) 0.98332(10) 0.0363(5) Uani 1 1 d . . . . .
H10 H 0.978195 0.626271 1.035235 0.044 Uiso 1 1 calc R U . . .
C11 C 0.9674(2) 0.66222(5) 0.94326(10) 0.0335(5) Uani 1 1 d . . . . .
C12 C 0.9278(2) 0.66219(5) 0.86568(10) 0.0318(5) Uani 1 1 d . . . . .
H12 H 0.937993 0.686543 0.839583 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6799(2) 0.69977(6) 0.58533(11) 0.0377(5) Uani 1 1 d . . . . .
C14 C 0.8237(2) 0.54916(6) 0.58650(11) 0.0374(5) Uani 1 1 d . . . . .
C15 C 1.0261(2) 0.70120(6) 0.98275(11) 0.0394(5) Uani 1 1 d . . . . .
C16 C 0.8784(2) 0.55113(6) 0.98566(11) 0.0387(5) Uani 1 1 d . . . . .
O9 O 0.6920(2) 0.73179(5) 0.91140(9) 0.0659(6) Uani 1 1 d . . . . .
O10 O 0.7034(2) 0.69934(5) 1.01924(9) 0.0686(6) Uani 1 1 d . . . . .
H10A H 0.759685 0.716849 1.035621 0.103 Uiso 1 1 calc R U . . .
O11 O 0.5735(2) 0.55072(5) 1.02084(8) 0.0621(6) Uani 1 1 d . . . . .
H11 H 0.546988 0.530089 1.039141 0.093 Uiso 1 1 calc R U . . .
O12 O 0.46740(19) 0.51992(4) 0.91423(8) 0.0581(5) Uani 1 1 d . . . . .
C17 C 0.6136(2) 0.66172(5) 0.90845(10) 0.0347(5) Uani 1 1 d . . . . .
C18 C 0.6002(2) 0.62532(5) 0.94832(11) 0.0367(5) Uani 1 1 d . . . . .
H18 H 0.626779 0.625119 1.000213 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5465(2) 0.58923(6) 0.90920(10) 0.0345(5) Uani 1 1 d . . . . .
C20 C 0.5069(2) 0.58933(5) 0.83151(10) 0.0326(5) Uani 1 1 d . . . . .
C21 C 0.52031(19) 0.62590(5) 0.79148(10) 0.0308(5) Uani 1 1 d . . . . .
C22 C 0.5742(2) 0.66202(5) 0.83124(10) 0.0326(5) Uani 1 1 d . . . . .
H22 H 0.583598 0.686561 0.805418 0.039 Uiso 1 1 calc R U . . .
C23 C 0.6730(2) 0.70038(6) 0.94865(11) 0.0396(5) Uani 1 1 d . . . . .
C24 C 0.5271(2) 0.55034(6) 0.94963(11) 0.0393(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C13 1.275(2) . ?
O2 C13 1.249(2) . ?
O3 H3 0.8200 . ?
O3 C14 1.278(2) . ?
O4 C14 1.240(2) . ?
O5 C16 1.237(2) . ?
O6 H6 0.8200 . ?
O6 C16 1.273(2) . ?
O7 H7 0.8200 . ?
O7 C15 1.276(2) . ?
O8 C15 1.244(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.385(2) . ?
C1 C13 1.489(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(3) . ?
C3 C4 1.388(3) . ?
C3 C14 1.489(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(2) . ?
C5 C6 1.394(2) . ?
C5 C7 1.477(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.401(2) . ?
C7 C12 1.396(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(2) . ?
C9 C10 1.390(3) . ?
C9 C16 1.492(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(3) . ?
C11 C12 1.390(3) . ?
C11 C15 1.487(3) . ?
C12 H12 0.9300 . ?
O9 C23 1.256(2) . ?
O10 H10A 0.8200 . ?
O10 C23 1.265(2) . ?
O11 H11 0.8200 . ?
O11 C24 1.285(2) . ?
O12 C24 1.245(2) . ?
C17 C18 1.394(3) . ?
C17 C22 1.384(3) . ?
C17 C23 1.486(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.393(3) . ?
C19 C20 1.392(2) . ?
C19 C24 1.481(3) . ?
C20 C21 1.400(2) . ?
C21 C21 1.486(3) 2_656 ?
C21 C22 1.400(2) . ?
C22 H22 0.9300 . ?

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
C13 O1 H1 109.5 . . ?
C14 O3 H3 109.5 . . ?
C16 O6 H6 109.5 . . ?
C15 O7 H7 109.5 . . ?
C2 C1 C13 120.16(16) . . ?
C6 C1 C2 120.46(15) . . ?
C6 C1 C13 119.36(15) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.90(16) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C14 120.62(16) . . ?
C4 C3 C2 120.44(15) . . ?
C4 C3 C14 118.94(15) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.05(15) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C7 120.60(15) . . ?
C6 C5 C4 117.79(15) . . ?
C6 C5 C7 121.60(15) . . ?
C1 C6 C5 121.33(15) . . ?
C1 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C8 C7 C5 120.63(15) . . ?
C12 C7 C5 121.62(15) . . ?
C12 C7 C8 117.75(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.24(16) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 120.51(15) . . ?
C8 C9 C16 118.77(16) . . ?
C10 C9 C16 120.72(16) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.06(16) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 120.36(16) . . ?
C10 C11 C15 120.49(16) . . ?
C12 C11 C15 119.15(16) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.08(16) . . ?
C11 C12 H12 119.5 . . ?
O1 C13 C1 117.12(16) . . ?
O2 C13 O1 123.93(17) . . ?
O2 C13 C1 118.95(16) . . ?
O3 C14 C3 116.17(16) . . ?
O4 C14 O3 124.22(17) . . ?
O4 C14 C3 119.61(17) . . ?
O7 C15 C11 116.51(17) . . ?
O8 C15 O7 124.08(17) . . ?
O8 C15 C11 119.41(17) . . ?
O5 C16 O6 124.50(17) . . ?
O5 C16 C9 119.07(17) . . ?
O6 C16 C9 116.43(16) . . ?
C23 O10 H10A 109.5 . . ?
C24 O11 H11 109.5 . . ?
C18 C17 C23 120.12(17) . . ?
C22 C17 C18 120.54(16) . . ?
C22 C17 C23 119.33(17) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 118.97(17) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C24 120.57(17) . . ?
C20 C19 C18 120.73(16) . . ?
C20 C19 C24 118.68(16) . . ?
C19 C20 C21 120.29(16) . . ?
C20 C21 C21 120.37(12) . 2_656 ?
C22 C21 C20 118.58(16) . . ?
C22 C21 C21 121.04(12) . 2_656 ?
C17 C22 C21 120.88(16) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
O9 C23 O10 123.69(17) . . ?
O9 C23 C17 118.93(18) . . ?
O10 C23 C17 117.37(17) . . ?
O11 C24 C19 116.35(16) . . ?
O12 C24 O11 124.01(17) . . ?
O12 C24 C19 119.64(17) . . ?

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
O1 H1 O8 0.82 1.91 2.6346(19) 146.6 8_465 yes
O3 H3 O5 0.82 1.81 2.6243(19) 168.9 6_565 yes
O6 H6 O4 0.82 1.82 2.637(2) 170.3 6_566 yes
O7 H7 O2 0.82 1.80 2.617(2) 170.7 8_566 yes
O10 H10A O9 0.82 1.90 2.627(2) 147.7 7_667 yes
O11 H11 O12 0.82 1.83 2.626(2) 164.8 5_667 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
C1 C2 C3 C4 1.7(3) . . . . ?
C1 C2 C3 C14 -177.5(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C13 O1 -5.2(3) . . . . ?
C2 C1 C13 O2 174.2(2) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C14 O3 -5.9(3) . . . . ?
C2 C3 C14 O4 173.9(2) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C3 C4 C5 C7 -178.7(2) . . . . ?
C4 C3 C14 O3 175.0(2) . . . . ?
C4 C3 C14 O4 -5.2(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C7 C8 -35.6(3) . . . . ?
C4 C5 C7 C12 145.0(2) . . . . ?
C5 C7 C8 C9 179.93(19) . . . . ?
C5 C7 C12 C11 179.9(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C13 O1 176.6(2) . . . . ?
C6 C1 C13 O2 -4.0(3) . . . . ?
C6 C5 C7 C8 145.0(2) . . . . ?
C6 C5 C7 C12 -34.4(3) . . . . ?
C7 C5 C6 C1 -180.0(2) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C16 179.5(2) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C8 C9 C16 O5 -3.6(3) . . . . ?
C8 C9 C16 O6 176.9(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C11 C15 -179.6(2) . . . . ?
C10 C9 C16 O5 175.2(2) . . . . ?
C10 C9 C16 O6 -4.3(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C10 C11 C15 O7 -3.1(3) . . . . ?
C10 C11 C15 O8 176.2(2) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
C12 C11 C15 O7 176.9(2) . . . . ?
C12 C11 C15 O8 -3.8(3) . . . . ?
C13 C1 C2 C3 -178.6(2) . . . . ?
C13 C1 C6 C5 177.5(2) . . . . ?
C14 C3 C4 C5 177.3(2) . . . . ?
C15 C11 C12 C7 179.6(2) . . . . ?
C16 C9 C10 C11 -179.3(2) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C17 C18 C19 C24 -178.2(2) . . . . ?
C18 C17 C22 C21 -0.1(3) . . . . ?
C18 C17 C23 O9 175.2(2) . . . . ?
C18 C17 C23 O10 -3.8(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C24 O11 -6.5(3) . . . . ?
C18 C19 C24 O12 172.8(2) . . . . ?
C19 C20 C21 C21 179.2(2) . . . 2_656 ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C19 C24 O11 175.1(2) . . . . ?
C20 C19 C24 O12 -5.6(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C21 C21 C22 C17 -179.0(2) 2_656 . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C22 C17 C23 O9 -3.6(3) . . . . ?
C22 C17 C23 O10 177.4(2) . . . . ?
C23 C17 C18 C19 -178.8(2) . . . . ?
C23 C17 C22 C21 178.7(2) . . . . ?
C24 C19 C20 C21 178.2(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.869 0.123 0.250 596.7 121.9 ?
2 -0.603 -0.123 0.750 596.7 121.9 ?
3 -0.575 0.377 0.750 596.7 121.9 ?
4 -0.098 0.623 0.250 596.7 121.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_platon_squeeze_void_probe_radius 1.20
_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 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.747
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5263(17) 12568 8409 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4737(17) 12534 8409 nmt -0.9805 0.0000 0.0392 0.0000 -1.0002 0.0002 0.9899
0.0001 0.9804

_twin_special_details            
;
Component 2 rotated by -179.9754° 
around [0.02 0.00 1.00] (reciprocal) or [0.45 0.00 0.89] (direct)
;
####################################################################### 
# 
# 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_TPTCA-2
_database_code_depnum_ccdc_archive 'CCDC 2277048'
loop_
_audit_author_name
_audit_author_address
'Peng Cui'
;Jiangsu University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 O8'
_chemical_formula_sum            'C22 H14 O8'
_chemical_formula_weight         406.33
_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 0.0033 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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   7.3463(3)
_cell_length_b                   26.5578(10)
_cell_length_c                   15.1916(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.149(4)
_cell_angle_gamma                90
_cell_volume                     2961.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4562
_cell_measurement_temperature    291
_cell_measurement_theta_max      29.3980
_cell_measurement_theta_min      2.6780
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.911
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10812
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_min         2.663
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  72.00   0.50   25.00    --   -8.90  43.00-175.00  186
  2  ω    -46.00   6.00   0.50   25.00    --   -8.90 -43.00  33.00  104
  3  ω    -94.00  25.00   0.50   25.00    --   -8.90 -57.00-150.00  238
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0734791000
_diffrn_orient_matrix_UB_12      0.0046573000
_diffrn_orient_matrix_UB_13      -0.0279253000
_diffrn_orient_matrix_UB_21      -0.0455475000
_diffrn_orient_matrix_UB_22      -0.0137468000
_diffrn_orient_matrix_UB_23      -0.0342640000
_diffrn_orient_matrix_UB_31      -0.0431570000
_diffrn_orient_matrix_UB_32      0.0224020000
_diffrn_orient_matrix_UB_33      -0.0152074000
_diffrn_oxdiff_digest_frames     
;
017d3301bb17390a5a949940a69bb139bd00025bb5c
;
_diffrn_oxdiff_digest_hkl        
;
012a51d85ed361a7640846da7cdab6851d5760
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2452
_reflns_number_total             3213
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.125
_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)+(0.1080P)²+0.0647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1676
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O3-H4
 2.263 with sigma of 0.002
 O2-H1 = O3-H4
 2.263 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C13(H13), C15(H15), C18(H18)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.61834(13) 0.74718(3) 0.34985(5) 0.0596(3) Uani 1 1 d . . . . .
H1 H 0.568764 0.758693 0.304967 0.089 Uiso 1 1 calc DGR . . . .
O2 O 0.54455(14) 0.67473(3) 0.28431(6) 0.0637(3) Uani 1 1 d D . . . .
O3 O 0.53120(14) 0.29330(3) 0.28743(6) 0.0612(3) Uani 1 1 d D . . . .
O4 O 0.60405(15) 0.22087(3) 0.35329(6) 0.0721(4) Uani 1 1 d . . . . .
H4 H 0.553505 0.209276 0.308715 0.108 Uiso 1 1 calc DGR . . . .
C5 C 0.750000 0.53695(5) 0.500000 0.0369(3) Uani 1 2 d S T P . .
C6 C 0.750000 0.43099(5) 0.500000 0.0368(3) Uani 1 2 d S T P . .
C7 C 0.750000 0.37506(5) 0.500000 0.0358(3) Uani 1 2 d S T P . .
C8 C 0.68742(13) 0.61995(4) 0.42632(6) 0.0380(3) Uani 1 1 d . . . . .
H8 H 0.645833 0.602710 0.376214 0.046 Uiso 1 1 calc R . . . .
C9 C 0.68611(13) 0.67202(4) 0.42648(6) 0.0377(3) Uani 1 1 d . . . . .
C10 C 0.750000 0.59285(5) 0.500000 0.0371(3) Uani 1 2 d S T P . .
C11 C 0.78302(16) 0.51005(3) 0.42404(7) 0.0415(3) Uani 1 1 d . . . . .
H11 H 0.806201 0.527284 0.372365 0.050 Uiso 1 1 calc R . . . .
C12 C 0.68029(13) 0.34816(4) 0.42767(6) 0.0376(3) Uani 1 1 d . . . . .
H12 H 0.633399 0.365428 0.378625 0.045 Uiso 1 1 calc R . . . .
C13 C 0.78201(14) 0.45788(4) 0.42392(7) 0.0410(3) Uani 1 1 d . . . . .
H13 H 0.803141 0.440645 0.372006 0.049 Uiso 1 1 calc R . . . .
C14 C 0.67986(13) 0.29607(4) 0.42782(6) 0.0386(3) Uani 1 1 d . . . . .
C15 C 0.750000 0.69872(5) 0.500000 0.0387(3) Uani 1 2 d S T P . .
H15 H 0.750000 0.733740 0.500001 0.046 Uiso 1 2 calc RS T P . .
C16 C 0.61110(14) 0.69928(4) 0.34760(7) 0.0416(3) Uani 1 1 d . . . . .
C17 C 0.59913(15) 0.26873(4) 0.35021(7) 0.0427(3) Uani 1 1 d . . . . .
C18 C 0.750000 0.26930(5) 0.500000 0.0408(4) Uani 1 2 d S T P . .
H18 H 0.750001 0.234280 0.499997 0.049 Uiso 1 2 calc RS T P . .


_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 H1 0.8200 . ?
O1 C16 1.2738(14) . ?
O2 C16 1.2464(12) . ?
O3 C17 1.2444(13) . ?
O4 H4 0.8200 . ?
O4 C17 1.2723(14) . ?
C5 C10 1.4847(19) . ?
C5 C11 1.3863(13) 2_656 ?
C5 C11 1.3863(13) . ?
C6 C7 1.4853(19) . ?
C6 C13 1.3862(12) 2_656 ?
C6 C13 1.3862(13) . ?
C7 C12 1.3920(12) 2_656 ?
C7 C12 1.3920(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.3829(14) . ?
C8 C10 1.3940(12) . ?
C9 C15 1.3898(12) . ?
C9 C16 1.4879(13) . ?
C11 H11 0.9300 . ?
C11 C13 1.3854(15) . ?
C12 H12 0.9300 . ?
C12 C14 1.3834(14) . ?
C13 H13 0.9300 . ?
C14 C17 1.4889(14) . ?
C14 C18 1.3897(12) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?

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
C16 O1 H1 109.5 . . ?
C17 O4 H4 109.5 . . ?
C11 C5 C10 121.02(6) . . ?
C11 C5 C10 121.02(6) 2_656 . ?
C11 C5 C11 117.96(13) . 2_656 ?
C13 C6 C7 121.02(6) . . ?
C13 C6 C7 121.02(6) 2_656 . ?
C13 C6 C13 117.97(13) 2_656 . ?
C12 C7 C6 120.88(6) 2_656 . ?
C12 C7 C6 120.88(6) . . ?
C12 C7 C12 118.25(12) 2_656 . ?
C9 C8 H8 119.4 . . ?
C9 C8 C10 121.13(9) . . ?
C10 C8 H8 119.4 . . ?
C8 C9 C15 120.63(9) . . ?
C8 C9 C16 119.18(9) . . ?
C15 C9 C16 120.17(10) . . ?
C8 C10 C5 121.08(6) . . ?
C8 C10 C5 121.08(6) 2_656 . ?
C8 C10 C8 117.85(13) 2_656 . ?
C5 C11 H11 119.5 . . ?
C13 C11 C5 121.02(10) . . ?
C13 C11 H11 119.5 . . ?
C7 C12 H12 119.6 . . ?
C14 C12 C7 120.85(9) . . ?
C14 C12 H12 119.6 . . ?
C6 C13 H13 119.5 . . ?
C11 C13 C6 121.02(10) . . ?
C11 C13 H13 119.5 . . ?
C12 C14 C17 119.17(9) . . ?
C12 C14 C18 120.81(9) . . ?
C18 C14 C17 120.01(10) . . ?
C9 C15 C9 118.63(13) 2_656 . ?
C9 C15 H15 120.7 . . ?
C9 C15 H15 120.7 2_656 . ?
O1 C16 C9 116.78(9) . . ?
O2 C16 O1 123.91(9) . . ?
O2 C16 C9 119.31(10) . . ?
O3 C17 O4 124.20(9) . . ?
O3 C17 C14 119.17(10) . . ?
O4 C17 C14 116.63(9) . . ?
C14 C18 C14 118.45(13) 2_656 . ?
C14 C18 H18 120.8 2_656 . ?
C14 C18 H18 120.8 . . ?

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 C11 C13 C6 -0.74(14) . . . . ?
C6 C7 C12 C14 -179.81(7) . . . . ?
C7 C6 C13 C11 -179.64(7) . . . . ?
C7 C12 C14 C17 178.23(8) . . . . ?
C7 C12 C14 C18 -0.37(15) . . . . ?
C8 C9 C15 C9 -0.47(7) . . . 2_656 ?
C8 C9 C16 O1 -177.79(10) . . . . ?
C8 C9 C16 O2 2.73(16) . . . . ?
C9 C8 C10 C5 179.52(7) . . . . ?
C9 C8 C10 C8 -0.48(7) . . . 2_656 ?
C10 C5 C11 C13 -179.64(7) . . . . ?
C10 C8 C9 C15 0.96(15) . . . . ?
C10 C8 C9 C16 -177.55(8) . . . . ?
C11 C5 C10 C8 -145.60(7) 2_656 . . . ?
C11 C5 C10 C8 34.40(7) 2_656 . . 2_656 ?
C11 C5 C10 C8 -145.60(7) . . . 2_656 ?
C11 C5 C10 C8 34.40(7) . . . . ?
C11 C5 C11 C13 0.36(7) 2_656 . . . ?
C12 C7 C12 C14 0.19(7) 2_656 . . . ?
C12 C14 C17 O3 -1.11(16) . . . . ?
C12 C14 C17 O4 179.24(10) . . . . ?
C12 C14 C18 C14 0.19(7) . . . 2_656 ?
C13 C6 C7 C12 143.23(7) 2_656 . . . ?
C13 C6 C7 C12 -36.77(7) . . . . ?
C13 C6 C7 C12 143.23(7) . . . 2_656 ?
C13 C6 C7 C12 -36.77(7) 2_656 . . 2_656 ?
C13 C6 C13 C11 0.36(7) 2_656 . . . ?
C15 C9 C16 O1 3.69(15) . . . . ?
C15 C9 C16 O2 -175.79(9) . . . . ?
C16 C9 C15 C9 178.02(11) . . . 2_656 ?
C17 C14 C18 C14 -178.41(11) . . . 2_656 ?
C18 C14 C17 O3 177.51(9) . . . . ?
C18 C14 C17 O4 -2.14(15) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.910 0.000 0.500 695.0 274.2 ?
2 -0.733 0.500 0.000 695.0 274.2 ?

_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 1.131
_oxdiff_exptl_absorpt_empirical_full_min 0.872
####################################################################### 
# 
# 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_TPTCA-1
_database_code_depnum_ccdc_archive 'CCDC 2277047'
loop_
_audit_author_name
_audit_author_address
'Peng Cui'
;Jiangsu University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 O8, [+ solvent]'
_chemical_formula_sum            'C22 H14 O8, [+ solvent]'
_chemical_formula_weight         406.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   16.4201(2)
_cell_length_b                   26.5063(3)
_cell_length_c                   7.19160(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.8240(10)
_cell_angle_gamma                90
_cell_volume                     2840.83(6)
_cell_formula_units_Z            4

_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10553
_cell_measurement_theta_max      35.28916893688418
_cell_measurement_theta_min      1.497116697222916
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.950
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9988322
_exptl_absorpt_process_details   
'CCP4 7.0.040: AIMLESS, version 0.5.32: 29/03/17 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean PILATUS_2M_S_N_24_0107_Diamond
_diffrn_detector_type            PILATUS_2M_S_N_24_0107_Diamond
_diffrn_reflns_number            13682
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.489
_diffrn_reflns_theta_max         25.165
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2778
_reflns_number_gt                1998
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       
'DIALS 2theta refinement, DIALS 1.6.4-g47a579eb-release'
_computing_data_collection       'Diamond I19 GDA, (Diamond, RAL, Didcot, UK)'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.6.4-g47a579eb-release
pointless (Evans, P., 2006)
XIA2 0.5.340-g5578c4a7-dials-1.6 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1261P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2778
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.34990(7) 0.25430(4) 0.47500(17) 0.0325(3) Uani 1 1 d . . . . .
H1 H 0.303046 0.242058 0.383386 0.049 Uiso 1 1 calc R U . . .
O2 O 0.28018(8) 0.32705(4) 0.34242(17) 0.0356(3) Uani 1 1 d . . . . .
H4 H 0.302(2) 0.7941(10) 0.348(4) 0.084(8) Uiso 1 1 d . . . . .
O3 O 0.28435(8) 0.71150(4) 0.32769(18) 0.0344(3) Uani 1 1 d . . . . .
O4 O 0.35872(9) 0.78365(4) 0.44744(19) 0.0365(4) Uani 1 1 d . . . . .
C1 C 0.500000 0.30346(8) 0.750000 0.0252(5) Uani 1 2 d S T P . .
H1A H 0.500000 0.267616 0.750007 0.030 Uiso 1 2 calc R U P . .
C2 C 0.42506(10) 0.33008(6) 0.6178(2) 0.0253(4) Uani 1 1 d . . . . .
C3 C 0.34507(10) 0.30343(6) 0.4674(2) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.42486(10) 0.38272(6) 0.6199(2) 0.0256(4) Uani 1 1 d . . . . .
H4A H 0.372646 0.400381 0.531033 0.031 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.40987(8) 0.750000 0.0257(5) Uani 1 2 d S T P . .
C6 C 0.500000 0.46582(8) 0.750000 0.0248(5) Uani 1 2 d S T P . .
C7 C 0.42090(11) 0.49302(6) 0.7066(2) 0.0271(4) Uani 1 1 d . . . . .
H7 H 0.366618 0.475321 0.677875 0.033 Uiso 1 1 calc R U . . .
C8 C 0.42049(11) 0.54517(6) 0.7050(2) 0.0256(4) Uani 1 1 d . . . . .
H8 H 0.365898 0.562814 0.673171 0.031 Uiso 1 1 calc R U . . .
C9 C 0.500000 0.57231(8) 0.750000 0.0251(5) Uani 1 2 d S T P . .
C10 C 0.500000 0.62834(8) 0.750000 0.0240(5) Uani 1 2 d S T P . .
C11 C 0.42679(10) 0.65514(6) 0.6110(2) 0.0251(4) Uani 1 1 d . . . . .
H11 H 0.376009 0.637417 0.516433 0.030 Uiso 1 1 calc R U . . .
C12 C 0.42733(10) 0.70816(6) 0.6093(2) 0.0256(4) Uani 1 1 d . . . . .
C13 C 0.500000 0.73469(8) 0.750000 0.0255(5) Uani 1 2 d S T P . .
H13 H 0.499999 0.770530 0.749997 0.031 Uiso 1 2 calc R U P . .
C14 C 0.35053(11) 0.73508(6) 0.4498(2) 0.0271(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.304(2) . ?
O1 H1 0.8400 . ?
O2 C3 1.2375(19) . ?
O3 C14 1.242(2) . ?
O4 C14 1.295(2) . ?
O4 H4 0.95(3) . ?
C1 C2 1.3906(19) . ?
C1 C2 1.3907(19) 2_656 ?
C1 H1A 0.9500 . ?
C2 C4 1.395(2) . ?
C2 C3 1.484(2) . ?
C4 C5 1.3951(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.483(3) . ?
C6 C7 1.401(2) 2_656 ?
C6 C7 1.402(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4043(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.485(3) . ?
C10 C11 1.3929(19) . ?
C10 C11 1.3929(19) 2_656 ?
C11 C12 1.405(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3888(19) . ?
C12 C14 1.483(2) . ?
C13 H13 0.9500 . ?

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 O1 H1 109.5 . . ?
C14 O4 H4 103.1(16) . . ?
C2 C1 C2 119.0(2) . 2_656 ?
C2 C1 H1A 120.5 . . ?
C2 C1 H1A 120.5 2_656 . ?
C1 C2 C4 120.37(15) . . ?
C1 C2 C3 121.00(14) . . ?
C4 C2 C3 118.59(14) . . ?
O2 C3 O1 123.66(14) . . ?
O2 C3 C2 121.15(14) . . ?
O1 C3 C2 115.17(13) . . ?
C5 C4 C2 121.17(15) . . ?
C5 C4 H4A 119.4 . . ?
C2 C4 H4A 119.4 . . ?
C4 C5 C4 117.9(2) 2_656 . ?
C4 C5 C6 121.05(10) 2_656 . ?
C4 C5 C6 121.05(10) . . ?
C7 C6 C7 118.1(2) 2_656 . ?
C7 C6 C5 120.96(10) 2_656 . ?
C7 C6 C5 120.97(10) . . ?
C8 C7 C6 121.14(15) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.64(15) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C8 118.4(2) . 2_656 ?
C8 C9 C10 120.82(10) . . ?
C8 C9 C10 120.82(10) 2_656 . ?
C11 C10 C11 118.7(2) . 2_656 ?
C11 C10 C9 120.67(10) . . ?
C11 C10 C9 120.67(10) 2_656 . ?
C10 C11 C12 120.64(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.43(15) . . ?
C13 C12 C14 120.74(14) . . ?
C11 C12 C14 118.78(14) . . ?
C12 C13 C12 119.2(2) 2_656 . ?
C12 C13 H13 120.4 2_656 . ?
C12 C13 H13 120.4 . . ?
O3 C14 O4 123.78(15) . . ?
O3 C14 C12 120.80(15) . . ?
O4 C14 C12 115.41(14) . . ?

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
C2 C1 C2 C4 -0.75(10) 2_656 . . . ?
C2 C1 C2 C3 177.17(15) 2_656 . . . ?
C1 C2 C3 O2 -176.17(12) . . . . ?
C4 C2 C3 O2 1.8(2) . . . . ?
C1 C2 C3 O1 2.28(19) . . . . ?
C4 C2 C3 O1 -179.75(13) . . . . ?
C1 C2 C4 C5 1.5(2) . . . . ?
C3 C2 C4 C5 -176.45(11) . . . . ?
C2 C4 C5 C4 -0.76(10) . . . 2_656 ?
C2 C4 C5 C6 179.24(10) . . . . ?
C4 C5 C6 C7 31.67(10) 2_656 . . 2_656 ?
C4 C5 C6 C7 -148.33(10) . . . 2_656 ?
C4 C5 C6 C7 -148.33(10) 2_656 . . . ?
C4 C5 C6 C7 31.67(10) . . . . ?
C7 C6 C7 C8 0.48(10) 2_656 . . . ?
C5 C6 C7 C8 -179.52(10) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C7 C8 C9 C8 0.47(10) . . . 2_656 ?
C7 C8 C9 C10 -179.53(10) . . . . ?
C8 C9 C10 C11 -35.14(10) . . . . ?
C8 C9 C10 C11 144.86(10) 2_656 . . . ?
C8 C9 C10 C11 144.86(10) . . . 2_656 ?
C8 C9 C10 C11 -35.14(10) 2_656 . . 2_656 ?
C11 C10 C11 C12 0.85(10) 2_656 . . . ?
C9 C10 C11 C12 -179.15(10) . . . . ?
C10 C11 C12 C13 -1.7(2) . . . . ?
C10 C11 C12 C14 176.03(11) . . . . ?
C11 C12 C13 C12 0.85(10) . . . 2_656 ?
C14 C12 C13 C12 -176.86(16) . . . 2_656 ?
C13 C12 C14 O3 -177.89(12) . . . . ?
C11 C12 C14 O3 4.4(2) . . . . ?
C13 C12 C14 O4 2.9(2) . . . . ?
C11 C12 C14 O4 -174.81(14) . . . . ?

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
O1 H1 O3 0.84 1.79 2.6183(15) 170.5 4_545 yes
O4 H4 O2 0.95(3) 1.70(3) 2.6227(17) 162(2) 4 yes

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.062

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.000 0.500 -0.123 651.4 234.5 ?
2 0.500 -0.000 -0.161 651.4 234.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2


####################################################################### 
# 
# 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_TPTCA-2_degas
_database_code_depnum_ccdc_archive 'CCDC 2277049'
loop_
_audit_author_name
_audit_author_address
'Peng Cui'
;Jiangsu University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_TPTCA-2_degas       
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal measurement was recorded after gas sorption isotherms, and the single crystal
quality is poor. The I/sig was <2.6 and the Rint was >0.37 above the 1-angstrom cutoff and was,
therefore, removed during data integration.  
;
# end Validation Reply Form

_audit_creation_date             2023-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 O8, [+ solvent]'
_chemical_formula_sum            'C22 H14 O8, [+ solvent]'
_chemical_formula_weight         406.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   9.364(4)
_cell_length_b                   27.147(5)
_cell_length_c                   10.077(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.60(5)
_cell_angle_gamma                90
_cell_volume                     2290.3(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    582
_cell_measurement_temperature    212(110)
_cell_measurement_theta_max      20.1660
_cell_measurement_theta_min      3.8680
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_min  0.21868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5147
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        20.815
_diffrn_reflns_theta_max         20.815
_diffrn_reflns_theta_min         3.889
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      212(110)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0489419000
_diffrn_orient_matrix_UB_12      0.0140828000
_diffrn_orient_matrix_UB_13      0.0635791000
_diffrn_orient_matrix_UB_21      -0.0315039000
_diffrn_orient_matrix_UB_22      0.0219893000
_diffrn_orient_matrix_UB_23      -0.0408158000
_diffrn_orient_matrix_UB_31      -0.0615287000
_diffrn_orient_matrix_UB_32      0.0000201000
_diffrn_orient_matrix_UB_33      0.0226467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                689
_reflns_number_total             1195
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       CrysAlisPro
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1195
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      0.929
_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)+(0.0951P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C6-C5 = C7-C6 = C8-C7 = C9-C10 = C11-C10 = C12-C11
 1.39 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3A), C6(H6), C7(H7), C10(H10), C12(H12)
3.b Tetrahedral OH refined with riding coordinates:
 O3(H3)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.2906(4) 0.30625(10) 0.2693(4) 0.0687(11) Uani 1 1 d . . . . .
H1 H 0.315551 0.294920 0.206027 0.103 Uiso 1 1 calc R U . . .
O2 O 0.3490(4) 0.37857(10) 0.1907(4) 0.0754(12) Uani 1 1 d . . . . .
O3 O 0.4691(4) 0.83455(10) 0.4223(4) 0.0806(13) Uani 1 1 d . . . . .
H3 H 0.536403 0.845880 0.398077 0.121 Uiso 1 1 calc R U . . .
O4 O 0.5565(4) 0.76204(10) 0.3715(4) 0.0729(11) Uani 1 1 d . . . . .
C1 C 0.250000 0.3542(2) 0.500000 0.0538(19) Uani 1 2 d S T P . .
H1A H 0.249998 0.319564 0.499999 0.065 Uiso 1 2 calc R U P . .
C2 C 0.2718(5) 0.38118(14) 0.3892(5) 0.0503(13) Uani 1 1 d . . . . .
C3 C 0.2711(6) 0.43323(15) 0.3897(5) 0.0583(14) Uani 1 1 d . . . . .
H3A H 0.284950 0.450115 0.314894 0.070 Uiso 1 1 calc R U . . .
C4 C 0.250000 0.46116(19) 0.500000 0.0508(18) Uani 1 2 d S T P . .
C5 C 0.250000 0.5169(2) 0.500000 0.0497(18) Uani 1 2 d DS T P . .
C6 C 0.2013(6) 0.54461(14) 0.5920(6) 0.0698(17) Uani 1 1 d D . . . .
H6 H 0.167153 0.527869 0.654382 0.084 Uiso 1 1 calc R U . . .
C7 C 0.2027(6) 0.59663(14) 0.5926(6) 0.0662(16) Uani 1 1 d D . . . .
H7 H 0.171238 0.613598 0.656482 0.079 Uiso 1 1 calc R U . . .
C8 C 0.250000 0.62364(19) 0.500000 0.0478(17) Uani 1 2 d DS T P . .
C9 C 0.250000 0.67992(19) 0.500000 0.0467(17) Uani 1 2 d DS T P . .
C10 C 0.3489(5) 0.70716(13) 0.4548(5) 0.0521(13) Uani 1 1 d D . . . .
H10 H 0.414324 0.690074 0.421755 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3532(6) 0.75926(14) 0.4572(5) 0.0518(13) Uani 1 1 d D . . . .
C12 C 0.250000 0.7859(2) 0.500000 0.058(2) Uani 1 2 d DS T P . .
H12 H 0.250003 0.820490 0.500001 0.070 Uiso 1 2 calc R U P . .
C13 C 0.3041(6) 0.35449(15) 0.2729(5) 0.0521(14) Uani 1 1 d . . . . .
C14 C 0.4682(6) 0.78650(16) 0.4136(5) 0.0535(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8300 . ?
O1 C13 1.315(4) . ?
O2 C13 1.266(4) . ?
O3 H3 0.8300 . ?
O3 C14 1.307(4) . ?
O4 C14 1.273(4) . ?
C1 H1A 0.9400 . ?
C1 C2 1.425(5) . ?
C1 C2 1.425(5) 2_556 ?
C2 C3 1.413(5) . ?
C2 C13 1.519(5) . ?
C3 H3A 0.9400 . ?
C3 C4 1.430(5) . ?
C4 C5 1.514(7) . ?
C5 C6 1.418(4) . ?
C5 C6 1.418(4) 2_556 ?
C6 H6 0.9400 . ?
C6 C7 1.412(5) . ?
C7 H7 0.9400 . ?
C7 C8 1.405(4) . ?
C8 C9 1.528(7) . ?
C9 C10 1.411(4) . ?
C9 C10 1.411(4) 2_556 ?
C10 H10 0.9400 . ?
C10 C11 1.415(5) . ?
C11 C12 1.419(4) . ?
C11 C14 1.524(5) . ?
C12 H12 0.9400 . ?

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
C13 O1 H1 109.5 . . ?
C14 O3 H3 109.5 . . ?
C2 C1 H1A 121.0 2_556 . ?
C2 C1 H1A 121.0 . . ?
C2 C1 C2 118.1(5) 2_556 . ?
C1 C2 C13 120.5(3) . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 C13 118.9(4) . . ?
C2 C3 H3A 118.8 . . ?
C2 C3 C4 122.4(4) . . ?
C4 C3 H3A 118.8 . . ?
C3 C4 C3 116.0(5) . 2_556 ?
C3 C4 C5 122.0(2) 2_556 . ?
C3 C4 C5 122.0(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 C4 122.0(2) 2_556 . ?
C6 C5 C6 116.0(5) . 2_556 ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(4) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(4) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C7 117.1(5) 2_556 . ?
C7 C8 C9 121.5(2) . . ?
C7 C8 C9 121.5(2) 2_556 . ?
C10 C9 C8 121.6(2) 2_556 . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 C10 116.8(5) . 2_556 ?
C9 C10 H10 118.8 . . ?
C9 C10 C11 122.4(4) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 C14 119.9(3) . . ?
C12 C11 C14 120.4(3) . . ?
C11 C12 C11 118.8(5) 2_556 . ?
C11 C12 H12 120.6 . . ?
C11 C12 H12 120.6 2_556 . ?
O1 C13 C2 116.5(3) . . ?
O2 C13 O1 123.5(3) . . ?
O2 C13 C2 119.9(3) . . ?
O3 C14 C11 116.7(4) . . ?
O4 C14 O3 123.8(4) . . ?
O4 C14 C11 119.5(4) . . ?

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
O1 H1 O4 0.83 1.92 2.705(4) 158.0 4_545 yes
O3 H3 O2 0.83 1.90 2.713(4) 167.5 4 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
C1 C2 C3 C4 0.5(7) . . . . ?
C1 C2 C13 O1 8.3(6) . . . . ?
C1 C2 C13 O2 -168.4(4) . . . . ?
C2 C1 C2 C3 -0.2(3) 2_556 . . . ?
C2 C1 C2 C13 176.8(5) 2_556 . . . ?
C2 C3 C4 C3 -0.2(3) . . . 2_556 ?
C2 C3 C4 C5 179.8(3) . . . . ?
C3 C2 C13 O1 -174.6(4) . . . . ?
C3 C2 C13 O2 8.7(7) . . . . ?
C3 C4 C5 C6 168.6(4) 2_556 . . 2_556 ?
C3 C4 C5 C6 -11.4(4) . . . 2_556 ?
C3 C4 C5 C6 168.6(4) . . . . ?
C3 C4 C5 C6 -11.4(4) 2_556 . . . ?
C4 C5 C6 C7 179.5(4) . . . . ?
C5 C6 C7 C8 1.1(8) . . . . ?
C6 C5 C6 C7 -0.5(4) 2_556 . . . ?
C6 C7 C8 C7 -0.5(4) . . . 2_556 ?
C6 C7 C8 C9 179.5(4) . . . . ?
C7 C8 C9 C10 155.7(3) 2_556 . . 2_556 ?
C7 C8 C9 C10 -24.3(3) . . . 2_556 ?
C7 C8 C9 C10 -24.3(3) 2_556 . . . ?
C7 C8 C9 C10 155.7(3) . . . . ?
C8 C9 C10 C11 -178.5(3) . . . . ?
C9 C10 C11 C12 -2.9(7) . . . . ?
C9 C10 C11 C14 177.2(4) . . . . ?
C10 C9 C10 C11 1.5(3) 2_556 . . . ?
C10 C11 C12 C11 1.4(3) . . . 2_556 ?
C10 C11 C14 O3 -178.2(4) . . . . ?
C10 C11 C14 O4 1.9(7) . . . . ?
C12 C11 C14 O3 2.0(6) . . . . ?
C12 C11 C14 O4 -178.0(4) . . . . ?
C13 C2 C3 C4 -176.7(3) . . . . ?
C14 C11 C12 C11 -178.7(5) . . . 2_556 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.076 0.000 0.500 257 29 ?
2 -0.061 0.500 0.000 257 29 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 5.661
_oxdiff_exptl_absorpt_empirical_full_min 0.586
