# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_jt-2-1xx-7
_database_code_depnum_ccdc_archive 'CCDC 2520616'
loop_
_audit_author_name
_audit_author_address
'Yoshinari Sawama'
;The University of Osaka
Japan
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-05-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7217)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O6'
_chemical_formula_sum            'C11 H12 O6'
_chemical_formula_weight         240.21
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H12 O6'
_chemical_oxdiff_usercomment     -170oC
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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   18.6238(2)
_cell_length_b                   8.18780(10)
_cell_length_c                   6.90540(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.1090(10)
_cell_angle_gamma                90
_cell_volume                     1052.99(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6297
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      75.3050
_cell_measurement_theta_min      5.8710
_cell_oxdiff_angle_alpha         89.971(2)
_cell_oxdiff_angle_beta          90.095(2)
_cell_oxdiff_angle_gamma         89.981(2)
_cell_oxdiff_length_a            18.6265(5)
_cell_oxdiff_length_b            8.1846(2)
_cell_oxdiff_length_c            6.9070(2)
_cell_oxdiff_measurement_reflns_used 6297
_cell_oxdiff_volume              1052.98(5)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 4 0.0471
3 -5 0 0.0229
4 4 -3 0.0509
-6 4 -2 0.0362
-12 0 0 0.0282
5 -4 3 0.0414
12 -1 0 0.0306
-9 -2 2 0.0467
9 2 -2 0.0467
-3 5 0 0.0070
-5 -5 0 0.0266
8 4 0 0.0245
8 -4 0 0.0256
-4 0 -4 0.0486
-1 -5 0 0.0217

_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.2229 -0.2341 4.1937 0.6386 0.2555 -0.7259
2.7696 -5.1425 -0.4626 -0.6565 -0.2626 -0.7071
4.3273 3.5589 -2.9182 -0.2629 0.6563 0.7072
-5.9651 3.5511 -2.4895 0.0365 -0.0927 0.9950
-12.0390 0.4649 0.1364 0.3320 -0.8306 0.4471
4.8935 -3.7019 2.6497 0.0004 0.0003 -1.0000
12.0204 -0.5675 -0.0566 -0.3275 0.8194 -0.4705
-9.2859 -2.2800 2.1370 0.3578 -0.8940 -0.2698
9.2859 2.2800 -2.1370 -0.3578 0.8940 0.2698
-3.2109 5.1215 -0.0049 0.5800 0.2319 0.7809
-4.8095 -4.8749 -0.0354 -0.3887 -0.7901 -0.4740
7.6276 4.1226 -0.0651 0.2344 0.9266 0.2939
7.9915 -3.9830 -0.1280 -0.5939 0.2184 -0.7743
-3.8323 -0.4459 -4.2334 -0.7220 -0.2886 0.6288
-0.7642 -5.3020 -0.0441 -0.5206 -0.5358 -0.6647

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9829
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.597
_diffrn_reflns_theta_min         4.749
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00 133.00   0.50    0.50    --   43.60  61.00 -68.00  246
  2  ω     75.00 198.00   0.50    0.88    --  108.70  61.00 -68.00  246
  3  ω     19.00 143.00   0.50    0.88    --  108.70 -61.00 152.00  248
  4  ω    -39.00   9.00   0.50    0.50    --  -35.00 -82.00  30.00   96
  5  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00-150.00   96
  6  ω    -46.00  78.00   0.50    0.50    --   43.60 -61.00 152.00  248
  7  ω     81.00 133.00   0.50    0.50    --   43.60  82.00-150.00  104
  8  ω      2.00  48.00   0.50    0.50    --   43.60  77.00-120.00   92
  9  ω     81.00 133.00   0.50    0.50    --   43.60  82.00  30.00  104
 10  ω      2.00  48.00   0.50    0.50    --   43.60  77.00  30.00   92
 11  ω     81.00 133.00   0.50    0.50    --   43.60  82.00-180.00  104
 12  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 -30.00   92
 13  ω     75.00 198.00   0.50    0.88    --  108.70  61.00  30.00  246
 14  ω     19.00 161.00   0.50    0.88    --  108.70 -30.00 -60.00  284
 15  ω     56.00 198.00   0.50    0.88    --  108.70  30.00  60.00  284
 16  ω     81.00 198.00   0.50    0.88    --  108.70  82.00-150.00  234
 17  ω     19.00 161.00   0.50    0.88    --  108.70 -30.00 -60.00  284
 18  ω     75.00 198.00   0.50    0.88    --  108.70  61.00 -30.00  246
 19  ω     19.00 198.00   0.50    0.88    --  108.70   0.00   0.00  358
 20  ω     56.00 198.00   0.50    0.88    --  108.70  30.00-180.00  284
 21  ω     81.00 198.00   0.50    0.88    --  108.70  82.00  60.00  234
 22  ω     81.00 198.00   0.50    0.88    --  108.70  82.00 -90.00  234
 23  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00-180.00   96
 24  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00  90.00   96
 25  ω      2.00  48.00   0.50    0.50    --   43.60  77.00  60.00   92
 26  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 150.00   92
 27  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 120.00   92
 28  ω    -40.00  88.00   0.50    0.50    --   43.60 -82.00 120.00  256
 29  ω    -46.00  77.00   0.50    0.50    --   43.60 -57.00 -30.00  246
 30  ω      2.00  48.00   0.50    0.50    --   43.60  77.00-180.00   92
 31  ω     69.00 122.00   0.50    0.88    --  108.70  45.00 -90.00  106
 32  ω     19.00 153.00   0.50    0.88    --  108.70 -82.00 -30.00  268
 33  ω     69.00 198.00   0.50    0.88    --  108.70  45.00-150.00  258
 34  ω     81.00 198.00   0.50    0.88    --  108.70  82.00 120.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0216883000
_diffrn_orient_matrix_UB_12      0.0998218000
_diffrn_orient_matrix_UB_13      0.1796787000
_diffrn_orient_matrix_UB_21      0.0724147000
_diffrn_orient_matrix_UB_22      0.0906821000
_diffrn_orient_matrix_UB_23      -0.0069269000
_diffrn_orient_matrix_UB_31      -0.0335618000
_diffrn_orient_matrix_UB_32      0.1313064000
_diffrn_orient_matrix_UB_33      -0.1319711000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                2083
_reflns_number_total             2130
_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 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 40.35a 64-bit (release 18-12-2018))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.085
_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)+(0.0554P)²+0.5227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0943
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.62060(11) 0.3240(2) 0.3780(3) 0.0195(5) Uani 1 1 d . . . . .
H1 H 0.654442 0.387944 0.351464 0.029 Uiso 1 1 calc R U . . .
O2 O 0.38280(11) 0.6779(2) 0.6022(3) 0.0204(5) Uani 1 1 d . . . . .
H2 H 0.347565 0.616480 0.623444 0.031 Uiso 1 1 calc R U . . .
O3 O 0.37868(12) 0.1752(2) 0.6476(3) 0.0209(5) Uani 1 1 d . . . . .
O4 O 0.31668(12) 0.4067(3) 0.6449(3) 0.0253(5) Uani 1 1 d . . . . .
O5 O 0.68526(11) 0.6011(2) 0.3338(3) 0.0214(5) Uani 1 1 d . . . . .
O6 O 0.62047(11) 0.8314(2) 0.3517(3) 0.0206(5) Uani 1 1 d . . . . .
C1 C 0.5000(2) 0.3258(3) 0.4824(5) 0.0179(6) Uani 1 1 d . . . . .
C2 C 0.56218(16) 0.4115(3) 0.4319(4) 0.0149(6) Uani 1 1 d . . . . .
C3 C 0.56283(18) 0.5851(3) 0.4337(4) 0.0165(6) Uani 1 1 d . . . . .
C4 C 0.50129(19) 0.6711(3) 0.4906(5) 0.0152(6) Uani 1 1 d . . . . .
H4 H 0.501188 0.787083 0.490447 0.018 Uiso 1 1 calc R U . . .
C5 C 0.44062(18) 0.5857(3) 0.5472(4) 0.0173(6) Uani 1 1 d . . . . .
C6 C 0.43952(18) 0.4149(3) 0.5453(4) 0.0153(6) Uani 1 1 d . . . . .
C7 C 0.50337(15) 0.1411(3) 0.4616(4) 0.0241(5) Uani 1 1 d . . . . .
H7A H 0.545153 0.111255 0.383142 0.036 Uiso 1 1 calc R U . . .
H7B H 0.459512 0.101969 0.398162 0.036 Uiso 1 1 calc R U . . .
H7C H 0.507605 0.091107 0.590031 0.036 Uiso 1 1 calc R U . . .
C8 C 0.62839(15) 0.6708(3) 0.3697(5) 0.0148(6) Uani 1 1 d . . . . .
C9 C 0.68266(19) 0.9169(3) 0.2771(5) 0.0225(7) Uani 1 1 d . . . . .
H9A H 0.723697 0.898774 0.363455 0.034 Uiso 1 1 calc R U . . .
H9B H 0.672268 1.034081 0.269757 0.034 Uiso 1 1 calc R U . . .
H9C H 0.694069 0.875679 0.147494 0.034 Uiso 1 1 calc R U . . .
C10 C 0.37258(16) 0.3321(3) 0.6148(4) 0.0186(6) Uani 1 1 d . . . . .
C11 C 0.31517(18) 0.0919(4) 0.7206(5) 0.0260(8) Uani 1 1 d . . . . .
H11A H 0.299427 0.144097 0.840910 0.039 Uiso 1 1 calc R U . . .
H11B H 0.326713 -0.022951 0.745859 0.039 Uiso 1 1 calc R U . . .
H11C H 0.276646 0.098366 0.624013 0.039 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 H1 0.8400 . ?
O1 C2 1.355(3) . ?
O2 H2 0.8400 . ?
O2 C5 1.369(4) . ?
O3 C10 1.310(3) . ?
O3 C11 1.456(3) . ?
O4 C10 1.225(4) . ?
O5 C8 1.229(4) . ?
O6 C8 1.330(3) . ?
O6 C9 1.449(4) . ?
C1 C2 1.398(4) . ?
C1 C6 1.411(5) . ?
C1 C7 1.521(4) . ?
C2 C3 1.422(4) . ?
C3 C4 1.402(5) . ?
C3 C8 1.476(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 C6 1.399(4) . ?
C6 C10 1.499(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C2 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
C10 O3 C11 116.7(2) . . ?
C8 O6 C9 115.0(2) . . ?
C2 C1 C6 118.7(2) . . ?
C2 C1 C7 116.2(3) . . ?
C6 C1 C7 125.2(3) . . ?
O1 C2 C1 118.0(2) . . ?
O1 C2 C3 121.6(3) . . ?
C1 C2 C3 120.4(3) . . ?
C2 C3 C8 118.6(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 C8 121.5(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
O2 C5 C4 116.3(2) . . ?
O2 C5 C6 122.8(3) . . ?
C4 C5 C6 120.9(3) . . ?
C1 C6 C10 122.0(3) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 C10 117.5(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5 C8 O6 122.4(3) . . ?
O5 C8 C3 123.6(3) . . ?
O6 C8 C3 114.0(3) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 C6 115.3(2) . . ?
O4 C10 O3 122.2(3) . . ?
O4 C10 C6 122.5(3) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 C2 C3 C4 -179.9(3) . . . . ?
O1 C2 C3 C8 1.8(4) . . . . ?
O2 C5 C6 C1 178.3(3) . . . . ?
O2 C5 C6 C10 -2.5(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C1 C2 C3 C8 -176.9(3) . . . . ?
C1 C6 C10 O3 12.3(5) . . . . ?
C1 C6 C10 O4 -169.9(3) . . . . ?
C2 C1 C6 C5 3.3(4) . . . . ?
C2 C1 C6 C10 -175.8(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C8 O5 -7.8(5) . . . . ?
C2 C3 C8 O6 171.3(3) . . . . ?
C3 C4 C5 O2 179.5(3) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C3 C8 O5 173.9(3) . . . . ?
C4 C3 C8 O6 -6.9(4) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
C4 C5 C6 C10 178.1(3) . . . . ?
C5 C6 C10 O3 -166.8(3) . . . . ?
C5 C6 C10 O4 10.9(5) . . . . ?
C6 C1 C2 O1 177.8(3) . . . . ?
C6 C1 C2 C3 -3.5(4) . . . . ?
C7 C1 C2 O1 -3.0(4) . . . . ?
C7 C1 C2 C3 175.7(3) . . . . ?
C7 C1 C6 C5 -175.8(3) . . . . ?
C7 C1 C6 C10 5.1(5) . . . . ?
C8 C3 C4 C5 179.1(3) . . . . ?
C9 O6 C8 O5 3.0(4) . . . . ?
C9 O6 C8 C3 -176.2(3) . . . . ?
C11 O3 C10 O4 0.5(4) . . . . ?
C11 O3 C10 C6 178.3(3) . . . . ?

_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 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.930
####################################################################### 
# 
# 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_jt-2-200-1
_database_code_depnum_ccdc_archive 'CCDC 2520617'
loop_
_audit_author_name
_audit_author_address
'Yoshinari Sawama'
;The University of Osaka
Japan
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 O11'
_chemical_formula_sum            'C19 H22 O11'
_chemical_formula_weight         426.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H22 O11'
_chemical_oxdiff_usercomment     -170oC
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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   37.20872(15)
_cell_length_b                   29.73371(15)
_cell_length_c                   7.45609(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8249.07(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    70903
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      75.8540
_cell_measurement_theta_min      2.3660
_cell_oxdiff_angle_alpha         89.9913(6)
_cell_oxdiff_angle_beta          89.9964(4)
_cell_oxdiff_angle_gamma         90.0064(5)
_cell_oxdiff_length_a            37.19543(17)
_cell_oxdiff_length_b            29.7402(2)
_cell_oxdiff_length_c            7.45713(4)
_cell_oxdiff_measurement_reflns_used 70902
_cell_oxdiff_volume              8249.07(9)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.108a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 19 0 0.0838
1 3 5 0.0929
1 -19 0 0.0766
-1 0 -5 0.0998
24 2 0 0.0812
11 15 2 0.1063
-24 -1 0 0.0396
3 -17 -2 0.1107
22 -7 -1 0.0708
-19 10 2 0.0590
21 0 2 0.0812
19 -12 0 0.0724
16 -3 -3 0.0813
9 18 0 0.0904

_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.121
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0442 19.2867 -0.0051 -0.2213 0.4176 0.8813
1.3144 2.5304 4.7916 0.3788 -0.7204 0.5810
1.0786 -19.2796 0.1198 0.2310 -0.4360 -0.8698
-1.4642 0.0162 -4.8316 -0.4113 0.7819 -0.4685
24.0083 1.9634 -0.1405 0.8826 0.4652 0.0679
11.2083 15.3976 1.8644 0.4180 0.2212 0.8811
-24.0773 -0.8317 0.2925 -0.8847 -0.4662 -0.0014
3.3637 -16.7872 -2.2937 0.1167 0.0604 -0.9913
21.5190 -7.0536 -1.3006 0.7875 0.4145 -0.4561
-19.2274 9.7303 1.6189 -0.7022 -0.3694 0.6086
21.1544 0.0471 2.3334 0.9744 -0.0378 0.2218
18.7582 -12.1487 -0.1034 0.8187 0.0545 -0.5716
16.4128 -2.6344 -3.4881 0.3911 0.7942 -0.4651
9.4833 17.7492 0.0852 0.1994 0.5422 0.8162

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            90511
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.993
_diffrn_reflns_theta_min         3.806
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00  12.00   0.50    0.50    --  -35.00 -38.00  30.00  242
  2  ω     81.00 132.00   0.50    0.50    --   42.60  82.00  90.00  102
  3  ω    -47.00 132.00   0.50    0.50    --   42.60  19.00  30.00  358
  4  ω     81.00 132.00   0.50    0.50    --   42.60  82.00 120.00  102
  5  ω    -47.00 132.00   0.50    0.50    --   42.60  19.00  30.00  358
  6  ω     75.00 132.00   0.50    0.50    --   42.60  77.00-150.00  114
  7  ω     81.00 134.00   0.50    0.50    --   44.60  82.00  30.00  106
  8  ω      2.00  48.00   0.50    0.50    --   44.60  77.00 120.00   92
  9  ω    -45.00  92.00   0.50    0.50    --   44.60 -38.00  90.00  274
 10  ω      2.00  48.00   0.50    0.50    --   44.60  77.00 150.00   92
 11  ω      2.00  48.00   0.50    0.50    --   44.60  77.00-180.00   92
 12  ω     20.00 155.00   0.50    0.50    --  109.30 -82.00 -30.00  270
 13  ω     74.00 199.00   0.50    0.50    --  109.30  61.00 120.00  250
 14  ω     82.00 199.00   0.50    0.50    --  109.30  82.00-120.00  234
 15  ω     20.00 145.00   0.50    0.50    --  109.30 -61.00 -30.00  250
 16  ω     20.00 155.00   0.50    0.50    --  109.30 -82.00 150.00  270
 17  ω     74.00 199.00   0.50    0.50    --  109.30  61.00   0.00  250
 18  ω     20.00 155.00   0.50    0.50    --  109.30 -82.00  90.00  270
 19  ω     76.00 199.00   0.50    0.50    --  109.30  77.00  90.00  246
 20  ω     82.00 199.00   0.50    0.50    --  109.30  82.00 -60.00  234
 21  ω     20.00 145.00   0.50    0.50    --  109.30 -61.00 150.00  250
 22  ω     68.00 199.00   0.50    0.50    --  109.30  45.00 -60.00  262
 23  ω     82.00 199.00   0.50    0.50    --  109.30  82.00-120.00  234
 24  ω     20.00 155.00   0.50    0.50    --  109.30 -82.00 150.00  270
 25  ω     20.00 155.00   0.50    0.50    --  109.30 -82.00 150.00  270
 26  ω     20.00 199.00   0.50    0.50    --  109.30 -15.00 -60.00  358
 27  ω    -80.00  39.00   0.50    0.50    --  -35.00  82.00 -30.00  238
 28  ω      2.00  48.00   0.50    0.50    --   44.60  77.00-120.00   92
 29  ω      2.00  48.00   0.50    0.50    --   44.60  77.00  30.00   92
 30  ω      2.00  48.00   0.50    0.50    --   44.60  77.00 -90.00   92
 31  ω     91.00 117.00   0.50    0.50    --   42.44   0.00 150.00   52
 32  ω    -28.00  -2.00   0.50    0.50    --   42.44   0.00 150.00   52
 33  ω      2.00  49.00   0.50    0.50    --   44.36  77.00-150.00   94
 34  ω      2.00  49.00   0.50    0.50    --   44.36  77.00 -30.00   94
 35  ω     76.00 134.00   0.50    0.50    --   44.36  77.00 150.00  116
 36  ω      2.00  49.00   0.50    0.50    --   44.36  77.00  90.00   94
 37  ω      2.00  49.00   0.50    0.50    --   44.36  77.00   0.00   94
 38  ω    -45.00  87.00   0.50    0.50    --   44.36 -77.00  60.00  264
 39  ω     82.00 134.00   0.50    0.50    --   44.36  82.00-180.00  104
 40  ω      2.00  49.00   0.50    0.50    --   44.36  77.00  60.00   94
 41  ω    -39.00  90.00   0.50    0.50    --   44.36 -82.00 -60.00  258
 42  ω     68.00 199.00   0.50    0.50    --  109.30  45.00-120.00  262
 43  ω     68.00 199.00   0.50    0.50    --  109.30  45.00-180.00  262
 44  ω     74.00 199.00   0.50    0.50    --  109.30  61.00-180.00  250
 45  ω     76.00 199.00   0.50    0.50    --  109.30  77.00-150.00  246
 46  ω     68.00 199.00   0.50    0.50    --  109.30  45.00 -30.00  262
 47  ω     68.00 199.00   0.50    0.50    --  109.30  45.00  90.00  262
 48  ω     68.00 199.00   0.50    0.50    --  109.30  45.00-150.00  262
 49  ω     68.00 199.00   0.50    0.50    --  109.30  45.00 150.00  262
 50  ω     74.00 199.00   0.50    0.50    --  109.30  61.00  30.00  250
 51  ω     20.00 155.00   0.50    0.50    --  109.30 -82.00-150.00  270
 52  ω     68.00 199.00   0.50    0.50    --  109.30  45.00  60.00  262
 53  ω     68.00 199.00   0.50    0.50    --  109.30  45.00  30.00  262
 54  ω     68.00 199.00   0.50    0.50    --  109.30  45.00 120.00  262
 55  ω     74.00 199.00   0.50    0.50    --  109.30  61.00  90.00  250
 56  ω     68.00 199.00   0.50    0.50    --  109.30  45.00   0.00  262
 57  ω     74.00 199.00   0.50    0.50    --  109.30  61.00-150.00  250
 58  ω     74.00 199.00   0.50    0.50    --  109.30  61.00  60.00  250
 59  ω     68.00 199.00   0.50    0.50    --  109.30  45.00 -90.00  262
 60  ω    -80.00  39.00   0.50    0.50    --  -35.00  82.00 -90.00  238
 61  ω    -47.00 132.00   0.50    0.50    --   42.44  19.00 -90.00  358
 62  ω    -39.00  88.00   0.50    0.50    --   42.44 -82.00 -30.00  254
 63  ω      0.00  49.00   0.50    0.50    --   42.44  77.00  60.00   98
 64  ω      2.00  49.00   0.50    0.50    --   44.36  77.00 -60.00   94
 65  ω    -45.00 134.00   0.50    0.50    --   44.36  19.00-150.00  358
 66  ω     -3.00 134.00   0.50    0.50    --   44.36  38.00  90.00  274
 67  ω    -45.00 134.00   0.50    0.50    --   44.36  19.00-180.00  358
 68  ω     -3.00 134.00   0.50    0.50    --   44.36  38.00 -30.00  274
 69  ω     74.00  76.00   0.50    0.50    --  109.30  61.00 -30.00    4
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0379621000
_diffrn_orient_matrix_UB_12      -0.0094008000
_diffrn_orient_matrix_UB_13      0.0736005000
_diffrn_orient_matrix_UB_21      0.0165595000
_diffrn_orient_matrix_UB_22      0.0225030000
_diffrn_orient_matrix_UB_23      -0.1667647000
_diffrn_orient_matrix_UB_31      -0.0003398000
_diffrn_orient_matrix_UB_32      0.0457008000
_diffrn_orient_matrix_UB_33      0.0972192000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4275
_reflns_number_total             4291
_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 1.171.44.108a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.112a 64-bit (release 21-05-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.108a (Rigaku OD, 2025)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0223
_refine_ls_restrained_S_all      1.063
_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)+(0.0333P)²+5.6034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0585
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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 0.54265(3) 0.51425(3) 0.43385(16) 0.0246(2) Uani 1 1 d . . . . .
O2 O 0.57390(3) 0.57896(4) 0.09413(15) 0.0236(2) Uani 1 1 d . . . . .
O3 O 0.59056(3) 0.61442(4) 0.34455(15) 0.0220(2) Uani 1 1 d . . . . .
O4 O 0.53320(3) 0.67675(4) 0.16926(16) 0.0251(2) Uani 1 1 d . . . . .
O5 O 0.50027(3) 0.70826(3) 0.38984(15) 0.0212(2) Uani 1 1 d . . . . .
O6 O 0.43571(3) 0.64826(4) 0.30979(17) 0.0322(3) Uani 1 1 d . . . . .
O7 O 0.43470(3) 0.67115(4) 0.59820(16) 0.0264(2) Uani 1 1 d . . . . .
O8 O 0.41727(3) 0.57750(4) 0.64873(18) 0.0309(3) Uani 1 1 d . . . . .
O9 O 0.45425(3) 0.53792(3) 0.82768(16) 0.0249(2) Uani 1 1 d . . . . .
O10 O 0.56041(3) 0.67767(3) 0.60039(14) 0.0189(2) Uani 1 1 d . . . . .
O11 O 0.59860(3) 0.72525(4) 0.74299(18) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.51755(4) 0.63319(5) 0.43145(19) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.48056(4) 0.62231(5) 0.51252(19) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.48059(4) 0.58657(5) 0.6204(2) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.51747(4) 0.56618(5) 0.65192(19) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.516926 0.540954 0.740567 0.022 Uiso 1 1 calc R U . . .
C5 C 0.53124(4) 0.55133(5) 0.4675(2) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.52940(4) 0.58960(5) 0.32633(19) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.50234(4) 0.57548(5) 0.1807(2) 0.0228(3) Uani 1 1 d . . . . .
H7A H 0.500739 0.599135 0.089565 0.034 Uiso 1 1 calc R U . . .
H7B H 0.478667 0.570877 0.235293 0.034 Uiso 1 1 calc R U . . .
H7C H 0.510400 0.547431 0.124625 0.034 Uiso 1 1 calc R U . . .
C8 C 0.54258(3) 0.63825(5) 0.59373(19) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.54335(4) 0.60337(5) 0.70588(19) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.558442 0.601903 0.808482 0.022 Uiso 1 1 calc R U . . .
C10 C 0.51821(4) 0.67483(5) 0.31221(19) 0.0178(3) Uani 1 1 d . . . . .
C11 C 0.49742(5) 0.74972(6) 0.2887(2) 0.0307(4) Uani 1 1 d . . . . .
H11A H 0.481746 0.744999 0.184775 0.046 Uiso 1 1 calc R U . . .
H11B H 0.521334 0.758914 0.247700 0.046 Uiso 1 1 calc R U . . .
H11C H 0.487239 0.773281 0.365320 0.046 Uiso 1 1 calc R U . . .
C12 C 0.56670(4) 0.59400(5) 0.23934(19) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.62556(4) 0.62139(6) 0.2632(2) 0.0285(4) Uani 1 1 d . . . . .
H13A H 0.622803 0.638917 0.152757 0.043 Uiso 1 1 calc R U . . .
H13B H 0.636422 0.592215 0.234995 0.043 Uiso 1 1 calc R U . . .
H13C H 0.641077 0.637756 0.346999 0.043 Uiso 1 1 calc R U . . .
C14 C 0.44769(4) 0.64830(5) 0.4594(2) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.40165(5) 0.69538(7) 0.5634(3) 0.0396(5) Uani 1 1 d . . . . .
H15A H 0.405885 0.718130 0.470620 0.059 Uiso 1 1 calc R U . . .
H15B H 0.393540 0.710126 0.673731 0.059 Uiso 1 1 calc R U . . .
H15C H 0.383175 0.674289 0.522178 0.059 Uiso 1 1 calc R U . . .
C16 C 0.44708(4) 0.56739(5) 0.6970(2) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.42309(5) 0.51596(6) 0.9028(3) 0.0426(5) Uani 1 1 d . . . . .
H17A H 0.411280 0.497933 0.809858 0.064 Uiso 1 1 calc R U . . .
H17B H 0.406290 0.538681 0.947855 0.064 Uiso 1 1 calc R U . . .
H17C H 0.430560 0.496341 1.001614 0.064 Uiso 1 1 calc R U . . .
C18 C 0.58566(4) 0.68201(5) 0.7468(2) 0.0229(3) Uani 1 1 d . . . . .
H18A H 0.573559 0.675993 0.862558 0.028 Uiso 1 1 calc R U . . .
H18B H 0.605605 0.660266 0.732322 0.028 Uiso 1 1 calc R U . . .
C19 C 0.62265(6) 0.73339(8) 0.5972(3) 0.0470(5) Uani 1 1 d . . . . .
H19A H 0.609543 0.730928 0.483625 0.070 Uiso 1 1 calc R U . . .
H19B H 0.642079 0.711148 0.599747 0.070 Uiso 1 1 calc R U . . .
H19C H 0.632814 0.763664 0.608282 0.070 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 C5 1.2076(18) . ?
O2 C12 1.2017(19) . ?
O3 C12 1.3313(17) . ?
O3 C13 1.4512(18) . ?
O4 C10 1.2042(19) . ?
O5 C10 1.3300(17) . ?
O5 C11 1.4488(18) . ?
O6 C14 1.201(2) . ?
O7 C14 1.3289(19) . ?
O7 C15 1.4488(19) . ?
O8 C16 1.2040(19) . ?
O9 C16 1.3372(19) . ?
O9 C17 1.4436(19) . ?
O10 C8 1.3480(17) . ?
O10 C18 1.4459(17) . ?
O11 C18 1.3732(19) . ?
O11 C19 1.428(3) . ?
C1 C2 1.5376(18) . ?
C1 C6 1.5775(19) . ?
C1 C8 1.5343(18) . ?
C1 C10 1.5245(19) . ?
C2 C3 1.333(2) . ?
C2 C14 1.4998(19) . ?
C3 C4 1.5186(18) . ?
C3 C16 1.486(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.532(2) . ?
C4 C9 1.520(2) . ?
C5 C6 1.5519(19) . ?
C6 C7 1.539(2) . ?
C6 C12 1.538(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.332(2) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C12 O3 C13 114.67(12) . . ?
C10 O5 C11 116.50(12) . . ?
C14 O7 C15 115.05(14) . . ?
C16 O9 C17 114.77(13) . . ?
C8 O10 C18 115.17(11) . . ?
C18 O11 C19 113.19(15) . . ?
C2 C1 C6 105.82(11) . . ?
C8 C1 C2 104.71(11) . . ?
C8 C1 C6 107.61(11) . . ?
C10 C1 C2 114.50(11) . . ?
C10 C1 C6 111.90(11) . . ?
C10 C1 C8 111.75(11) . . ?
C3 C2 C1 113.84(12) . . ?
C3 C2 C14 124.80(13) . . ?
C14 C2 C1 121.18(12) . . ?
C2 C3 C4 114.37(13) . . ?
C2 C3 C16 122.51(13) . . ?
C16 C3 C4 123.07(13) . . ?
C3 C4 H4 112.6 . . ?
C3 C4 C5 106.15(11) . . ?
C3 C4 C9 108.84(11) . . ?
C5 C4 H4 112.6 . . ?
C9 C4 H4 112.6 . . ?
C9 C4 C5 103.62(11) . . ?
O1 C5 C4 124.56(13) . . ?
O1 C5 C6 122.95(13) . . ?
C4 C5 C6 112.49(11) . . ?
C5 C6 C1 106.13(11) . . ?
C7 C6 C1 113.07(11) . . ?
C7 C6 C5 107.89(12) . . ?
C12 C6 C1 113.08(11) . . ?
C12 C6 C5 107.98(11) . . ?
C12 C6 C7 108.43(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O10 C8 C1 114.40(12) . . ?
C9 C8 O10 130.02(13) . . ?
C9 C8 C1 115.58(12) . . ?
C4 C9 H9 123.6 . . ?
C8 C9 C4 112.72(12) . . ?
C8 C9 H9 123.6 . . ?
O4 C10 O5 125.61(13) . . ?
O4 C10 C1 124.20(13) . . ?
O5 C10 C1 110.18(12) . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 123.50(14) . . ?
O2 C12 C6 123.35(13) . . ?
O3 C12 C6 113.09(12) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 O7 126.07(14) . . ?
O6 C14 C2 123.17(14) . . ?
O7 C14 C2 110.76(13) . . ?
O7 C15 H15A 109.5 . . ?
O7 C15 H15B 109.5 . . ?
O7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O8 C16 O9 124.41(14) . . ?
O8 C16 C3 124.22(14) . . ?
O9 C16 C3 111.37(12) . . ?
O9 C17 H17A 109.5 . . ?
O9 C17 H17B 109.5 . . ?
O9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O10 C18 H18A 110.3 . . ?
O10 C18 H18B 110.3 . . ?
O11 C18 O10 107.20(12) . . ?
O11 C18 H18A 110.3 . . ?
O11 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
O11 C19 H19A 109.5 . . ?
O11 C19 H19B 109.5 . . ?
O11 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C5 C6 C1 -173.16(13) . . . . ?
O1 C5 C6 C7 65.37(17) . . . . ?
O1 C5 C6 C12 -51.63(17) . . . . ?
O10 C8 C9 C4 177.30(13) . . . . ?
C1 C2 C3 C4 4.37(18) . . . . ?
C1 C2 C3 C16 -173.35(13) . . . . ?
C1 C2 C14 O6 63.8(2) . . . . ?
C1 C2 C14 O7 -115.19(14) . . . . ?
C1 C6 C12 O2 -141.36(14) . . . . ?
C1 C6 C12 O3 41.39(16) . . . . ?
C1 C8 C9 C4 -2.57(17) . . . . ?
C2 C1 C6 C5 -60.35(13) . . . . ?
C2 C1 C6 C7 57.74(15) . . . . ?
C2 C1 C6 C12 -178.55(11) . . . . ?
C2 C1 C8 O10 -124.93(12) . . . . ?
C2 C1 C8 C9 54.97(15) . . . . ?
C2 C1 C10 O4 -135.77(14) . . . . ?
C2 C1 C10 O5 44.78(16) . . . . ?
C2 C3 C4 C5 -60.87(15) . . . . ?
C2 C3 C4 C9 50.10(16) . . . . ?
C2 C3 C16 O8 11.8(2) . . . . ?
C2 C3 C16 O9 -167.44(13) . . . . ?
C3 C2 C14 O6 -111.13(18) . . . . ?
C3 C2 C14 O7 69.89(19) . . . . ?
C3 C4 C5 O1 -128.48(14) . . . . ?
C3 C4 C5 C6 52.19(14) . . . . ?
C3 C4 C9 C8 -50.76(16) . . . . ?
C4 C3 C16 O8 -165.69(15) . . . . ?
C4 C3 C16 O9 15.0(2) . . . . ?
C4 C5 C6 C1 6.19(15) . . . . ?
C4 C5 C6 C7 -115.28(13) . . . . ?
C4 C5 C6 C12 127.72(12) . . . . ?
C5 C4 C9 C8 61.88(14) . . . . ?
C5 C6 C12 O2 101.52(16) . . . . ?
C5 C6 C12 O3 -75.72(14) . . . . ?
C6 C1 C2 C3 58.04(15) . . . . ?
C6 C1 C2 C14 -117.40(14) . . . . ?
C6 C1 C8 O10 122.79(12) . . . . ?
C6 C1 C8 C9 -57.31(15) . . . . ?
C6 C1 C10 O4 -15.37(19) . . . . ?
C6 C1 C10 O5 165.18(11) . . . . ?
C7 C6 C12 O2 -15.13(18) . . . . ?
C7 C6 C12 O3 167.62(12) . . . . ?
C8 O10 C18 O11 -174.29(12) . . . . ?
C8 C1 C2 C3 -55.51(15) . . . . ?
C8 C1 C2 C14 129.04(13) . . . . ?
C8 C1 C6 C5 51.18(14) . . . . ?
C8 C1 C6 C7 169.27(12) . . . . ?
C8 C1 C6 C12 -67.02(15) . . . . ?
C8 C1 C10 O4 105.40(16) . . . . ?
C8 C1 C10 O5 -74.05(14) . . . . ?
C9 C4 C5 O1 116.94(15) . . . . ?
C9 C4 C5 C6 -62.40(13) . . . . ?
C10 C1 C2 C3 -178.24(12) . . . . ?
C10 C1 C2 C14 6.32(18) . . . . ?
C10 C1 C6 C5 174.31(11) . . . . ?
C10 C1 C6 C7 -67.60(15) . . . . ?
C10 C1 C6 C12 56.11(15) . . . . ?
C10 C1 C8 O10 -0.43(16) . . . . ?
C10 C1 C8 C9 179.46(12) . . . . ?
C11 O5 C10 O4 2.8(2) . . . . ?
C11 O5 C10 C1 -177.74(13) . . . . ?
C13 O3 C12 O2 6.0(2) . . . . ?
C13 O3 C12 C6 -176.78(12) . . . . ?
C14 C2 C3 C4 179.62(13) . . . . ?
C14 C2 C3 C16 1.9(2) . . . . ?
C15 O7 C14 O6 4.5(2) . . . . ?
C15 O7 C14 C2 -176.60(13) . . . . ?
C16 C3 C4 C5 116.83(14) . . . . ?
C16 C3 C4 C9 -132.20(14) . . . . ?
C17 O9 C16 O8 3.9(2) . . . . ?
C17 O9 C16 C3 -176.87(14) . . . . ?
C18 O10 C8 C1 -176.63(11) . . . . ?
C18 O10 C8 C9 3.5(2) . . . . ?
C19 O11 C18 O10 -72.18(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 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.871
####################################################################### 
# 
# 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_jt-me3-1
_database_code_depnum_ccdc_archive 'CCDC 2520623'
loop_
_audit_author_name
_audit_author_address
'Yoshinari Sawama'
;The University of Osaka
Japan
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O6'
_chemical_formula_sum            'C11 H12 O6'
_chemical_formula_weight         240.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H12 O6'
_chemical_oxdiff_usercomment     -170C
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1149(2)
_cell_length_b                   8.4497(3)
_cell_length_c                   11.0343(4)
_cell_angle_alpha                90.472(3)
_cell_angle_beta                 101.250(3)
_cell_angle_gamma                102.608(3)
_cell_volume                     544.92(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8904
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      75.2040
_cell_measurement_theta_min      4.0730
_cell_oxdiff_angle_alpha         90.472(3)
_cell_oxdiff_angle_beta          101.250(3)
_cell_oxdiff_angle_gamma         102.608(3)
_cell_oxdiff_length_a            6.1149(2)
_cell_oxdiff_length_b            8.4497(3)
_cell_oxdiff_length_c            11.0343(3)
_cell_oxdiff_measurement_reflns_used 8904
_cell_oxdiff_volume              544.92(3)
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.108a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -2 -3 0.0779
2 -5 2 0.0894
0 -4 5 0.0880
-3 0 5 0.0902
0 4 -5 0.0357
0 -2 -7 0.0886
3 3 -3 0.0563
0 2 6 0.0723
-1 0 7 0.0775
-3 -3 3 0.0967
-1 -3 -4 0.1000
4 0 1 0.0532
-4 -1 1 0.0827
0 0 7 0.0731
1 -5 0 0.0929
0 5 2 0.0781
2 1 5 0.0616

_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.128
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.7973 -1.9364 -3.0413 -0.7551 0.1089 0.6465
2.1042 -4.6015 2.4258 -0.9368 0.1349 -0.3228
-0.4521 -3.8240 5.0860 -0.5058 0.0727 -0.8596
-3.4784 0.2953 4.5085 0.4744 -0.0685 -0.8776
-0.2203 4.2237 -4.6137 0.6478 -0.0932 0.7561
0.1330 -1.6175 -6.6362 -0.1245 -0.8642 0.4875
2.5835 3.0645 -2.9051 0.0637 0.4428 0.8943
0.3296 2.1522 6.0645 0.1349 0.9364 -0.3239
-1.4089 -0.1758 7.0486 0.0729 0.5057 -0.8596
-2.5819 -2.9886 3.1737 -0.0583 -0.4056 -0.9122
-1.4631 -3.1940 -3.6842 -0.1411 -0.9795 -0.1437
3.7429 -0.0852 0.5022 -0.5638 0.6766 0.4737
-3.6582 -0.9708 1.2954 0.3875 -0.5787 -0.7176
0.1619 -0.0190 6.9500 -0.1341 0.7763 -0.6159
0.5173 -5.4494 -0.3109 -0.7724 -0.5173 -0.3685
0.0875 4.9905 2.0600 0.5980 0.7602 0.2538
1.9828 0.7485 5.0232 -0.2704 0.9556 -0.1167

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10041
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.442
_diffrn_reflns_theta_min         4.091
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  80.00   0.50    0.50    --   43.60 -67.00  31.00  252
  2  ω      8.00 133.00   0.50    0.50    --   43.60  67.00 165.00  250
  3  ω     73.00 198.00   0.50    0.50    --  108.70  67.00 165.00  250
  4  ω     19.00 145.00   0.50    0.50    --  108.70 -67.00  31.00  252
  5  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00   0.00   96
  6  ω    -39.00   8.00   0.50    0.50    --  -35.00 -82.00 -90.00   94
  7  ω    -70.00  54.00   0.50    0.50    --  -35.00  67.00 165.00  248
  8  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00-180.00   96
  9  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00-120.00   96
 10  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00  90.00   96
 11  ω   -124.00   1.00   0.50    0.50    --  -35.00 -67.00  31.00  250
 12  ω      2.00  48.00   0.50    0.50    --   43.60  77.00  90.00   92
 13  ω      2.00  48.00   0.50    0.50    --   43.60  77.00-120.00   92
 14  ω     81.00 133.00   0.50    0.50    --   43.60  82.00  60.00  104
 15  ω     60.00 198.00   0.50    0.50    --  108.70  30.00 -90.00  276
 16  ω     19.00 152.00   0.50    0.50    --  108.70 -82.00 120.00  266
 17  ω     19.00 143.00   0.50    0.50    --  108.70 -61.00-180.00  248
 18  ω     60.00 198.00   0.50    0.50    --  108.70  30.00 120.00  276
 19  ω     19.00 150.00   0.50    0.50    --  108.70 -77.00  90.00  262
 20  ω     19.00 152.00   0.50    0.50    --  108.70 -82.00  30.00  266
 21  ω     19.00 143.00   0.50    0.50    --  108.70 -61.00-150.00  248
 22  ω     19.00 198.00   0.50    0.50    --  108.70  15.00-180.00  358
 23  ω     19.00 152.00   0.50    0.50    --  108.70 -82.00-150.00  266
 24  ω     19.00 152.00   0.50    0.50    --  108.70 -82.00 -90.00  266
 25  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00 -60.00   96
 26  ω    -40.00  87.00   0.50    0.50    --   43.60 -82.00 -90.00  254
 27  ω      2.00  48.00   0.50    0.50    --   43.60  77.00-180.00   92
 28  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 -30.00   92
 29  ω     75.00 133.00   0.50    0.50    --   43.60  77.00   0.00  116
 30  ω     81.00 133.00   0.50    0.50    --   43.60  82.00 -90.00  104
 31  ω     75.00 133.00   0.50    0.50    --   43.60  77.00 -30.00  116
 32  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 -90.00   92
 33  ω      2.00  48.00   0.50    0.50    --   43.60  77.00  30.00   92
 34  ω     70.00 156.00   0.50    0.50    --  108.70  45.00  30.00  172
 35  ω     60.00 198.00   0.50    0.50    --  108.70  30.00   0.00  276
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1456144000
_diffrn_orient_matrix_UB_12      0.1288039000
_diffrn_orient_matrix_UB_13      -0.0155470000
_diffrn_orient_matrix_UB_21      0.1686493000
_diffrn_orient_matrix_UB_22      0.1047726000
_diffrn_orient_matrix_UB_23      0.1080633000
_diffrn_orient_matrix_UB_31      0.1408198000
_diffrn_orient_matrix_UB_32      0.0862256000
_diffrn_orient_matrix_UB_33      -0.0916611000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2190
_reflns_number_total             2223
_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 1.171.44.108a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 40.35a 64-bit (release 18-12-2018))'
_computing_data_reduction        'CrysAlisPro 1.171.44.108a (Rigaku OD, 2025)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.20907(12) 0.65304(9) 0.00559(7) 0.02052(18) Uani 1 1 d . . . . .
O2 O 0.70598(13) 0.35191(9) 0.34684(8) 0.02371(19) Uani 1 1 d . . . . .
H2 H 0.780326 0.409903 0.409971 0.036 Uiso 1 1 calc R U . . .
O3 O 0.39435(13) 0.95352(9) 0.19497(7) 0.02096(18) Uani 1 1 d . . . . .
O4 O 0.69754(12) 0.85382(8) 0.17261(7) 0.01812(17) Uani 1 1 d . . . . .
O5 O 0.81779(14) 0.60989(10) 0.49551(7) 0.02591(19) Uani 1 1 d . . . . .
O6 O 0.64262(13) 0.81465(9) 0.44298(7) 0.02286(19) Uani 1 1 d . . . . .
C1 C 0.38252(17) 0.66690(12) 0.22093(9) 0.0154(2) Uani 1 1 d . . . . .
C2 C 0.16604(18) 0.65921(13) 0.27540(10) 0.0201(2) Uani 1 1 d . . . . .
H2A H 0.209978 0.711555 0.358842 0.030 Uiso 1 1 calc R U . . .
H2B H 0.088322 0.545491 0.279354 0.030 Uiso 1 1 calc R U . . .
H2C H 0.062623 0.715692 0.222538 0.030 Uiso 1 1 calc R U . . .
C3 C 0.48885(17) 0.84257(12) 0.19719(9) 0.0157(2) Uani 1 1 d . . . . .
C4 C 0.81165(19) 1.01359(13) 0.14211(11) 0.0230(2) Uani 1 1 d . . . . .
H4A H 0.732536 1.040276 0.061425 0.035 Uiso 1 1 calc R U . . .
H4B H 0.970687 1.013706 0.138819 0.035 Uiso 1 1 calc R U . . .
H4C H 0.808716 1.094574 0.205515 0.035 Uiso 1 1 calc R U . . .
C5 C 0.29230(16) 0.58087(12) 0.09133(9) 0.0162(2) Uani 1 1 d . . . . .
C6 C 0.30307(18) 0.41044(12) 0.07735(10) 0.0197(2) Uani 1 1 d . . . . .
H6 H 0.214807 0.346422 0.006065 0.024 Uiso 1 1 calc R U . . .
C7 C 0.43566(18) 0.34372(12) 0.16372(10) 0.0202(2) Uani 1 1 d . . . . .
H7 H 0.442774 0.233730 0.151217 0.024 Uiso 1 1 calc R U . . .
C8 C 0.56934(17) 0.43499(12) 0.27634(10) 0.0179(2) Uani 1 1 d . . . . .
C9 C 0.55136(16) 0.58797(12) 0.30485(9) 0.0162(2) Uani 1 1 d . . . . .
C10 C 0.68309(18) 0.66849(13) 0.42212(10) 0.0188(2) Uani 1 1 d . . . . .
C11 C 0.7569(2) 0.89801(16) 0.56120(11) 0.0308(3) Uani 1 1 d . . . . .
H11A H 0.742286 1.011237 0.559765 0.046 Uiso 1 1 calc R U . . .
H11B H 0.919149 0.894806 0.576799 0.046 Uiso 1 1 calc R U . . .
H11C H 0.686375 0.844363 0.626991 0.046 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 C5 1.2179(12) . ?
O2 H2 0.8400 . ?
O2 C8 1.3445(12) . ?
O3 C3 1.2020(12) . ?
O4 C3 1.3392(12) . ?
O4 C4 1.4528(12) . ?
O5 C10 1.2263(13) . ?
O6 C10 1.3380(13) . ?
O6 C11 1.4493(13) . ?
C1 C2 1.5464(14) . ?
C1 C3 1.5317(13) . ?
C1 C5 1.5420(13) . ?
C1 C9 1.5186(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.4642(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3381(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.4559(15) . ?
C8 C9 1.3604(14) . ?
C9 C10 1.4580(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 O2 H2 109.5 . . ?
C3 O4 C4 115.69(8) . . ?
C10 O6 C11 116.46(9) . . ?
C3 C1 C2 110.46(8) . . ?
C3 C1 C5 105.02(8) . . ?
C5 C1 C2 104.62(8) . . ?
C9 C1 C2 110.51(8) . . ?
C9 C1 C3 112.19(8) . . ?
C9 C1 C5 113.67(8) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 O4 124.56(9) . . ?
O3 C3 C1 124.86(9) . . ?
O4 C3 C1 110.49(8) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C1 120.07(9) . . ?
O1 C5 C6 122.12(9) . . ?
C6 C5 C1 117.77(9) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.83(10) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.83(9) . . ?
C8 C7 H7 119.1 . . ?
O2 C8 C7 113.12(9) . . ?
O2 C8 C9 124.96(10) . . ?
C9 C8 C7 121.92(9) . . ?
C8 C9 C1 120.33(9) . . ?
C8 C9 C10 118.62(9) . . ?
C10 C9 C1 120.86(9) . . ?
O5 C10 O6 122.56(10) . . ?
O5 C10 C9 124.19(10) . . ?
O6 C10 C9 113.25(9) . . ?
O6 C11 H11A 109.5 . . ?
O6 C11 H11B 109.5 . . ?
O6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 C5 C6 C7 165.93(10) . . . . ?
O2 C8 C9 C1 -177.07(9) . . . . ?
O2 C8 C9 C10 -2.08(16) . . . . ?
C1 C5 C6 C7 -16.32(15) . . . . ?
C1 C9 C10 O5 178.12(10) . . . . ?
C1 C9 C10 O6 -1.74(14) . . . . ?
C2 C1 C3 O3 -15.04(14) . . . . ?
C2 C1 C3 O4 168.29(8) . . . . ?
C2 C1 C5 O1 79.62(11) . . . . ?
C2 C1 C5 C6 -98.18(10) . . . . ?
C2 C1 C9 C8 101.47(11) . . . . ?
C2 C1 C9 C10 -73.41(11) . . . . ?
C3 C1 C5 O1 -36.74(12) . . . . ?
C3 C1 C5 C6 145.46(9) . . . . ?
C3 C1 C9 C8 -134.77(10) . . . . ?
C3 C1 C9 C10 50.35(12) . . . . ?
C4 O4 C3 O3 0.27(14) . . . . ?
C4 O4 C3 C1 176.95(8) . . . . ?
C5 C1 C3 O3 97.23(11) . . . . ?
C5 C1 C3 O4 -79.44(9) . . . . ?
C5 C1 C9 C8 -15.80(13) . . . . ?
C5 C1 C9 C10 169.33(9) . . . . ?
C5 C6 C7 C8 1.76(16) . . . . ?
C6 C7 C8 O2 -174.80(10) . . . . ?
C6 C7 C8 C9 5.86(16) . . . . ?
C7 C8 C9 C1 2.19(15) . . . . ?
C7 C8 C9 C10 177.18(9) . . . . ?
C8 C9 C10 O5 3.16(16) . . . . ?
C8 C9 C10 O6 -176.70(9) . . . . ?
C9 C1 C3 O3 -138.82(10) . . . . ?
C9 C1 C3 O4 44.50(11) . . . . ?
C9 C1 C5 O1 -159.74(9) . . . . ?
C9 C1 C5 C6 22.47(13) . . . . ?
C11 O6 C10 O5 -3.49(15) . . . . ?
C11 O6 C10 C9 176.36(9) . . . . ?

_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.902
