# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2075802'
loop_
_audit_author_name
_audit_author_address
'Nobuhiro Yasuda'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2021-04-07 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT601_shelxl              
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        129 Ang**3
RESPONSE: There is a channel like void space in a center of ring molecule. 
Because the Q-peaks of solvent molecule were not clearly observed, 
the structure refinement inside the void was not carried out.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C42 H24 O12'
_chemical_formula_sum            'C42 H24 O12'
_chemical_formula_weight         720.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0022 '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 0.0146 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   14.2829(6)
_cell_length_b                   14.2829(6)
_cell_length_c                   5.2532(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     928.08(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3934
_cell_measurement_theta_min      1.878
_cell_measurement_theta_max      29.223

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.022
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.004
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3038
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.81078
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless ω scans'
_diffrn_detector_area_resol_mean 13.33
_diffrn_reflns_number            3934
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         29.223
_diffrn_reflns_theta_full        29.109
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1111
_reflns_number_gt                775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1511P)²+0.0593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.64(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1111
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2585
_refine_ls_wR_factor_gt          0.2377
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

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 0.12391(17) 0.50254(17) 0.8849(4) 0.0876(10) Uani 1 1 d . . . . .
O2 O -0.06101(19) 0.2312(2) 0.1218(5) 0.1071(11) Uani 1 1 d . . . . .
C1 C 0.1456(2) 0.4113(2) 0.5386(5) 0.0649(9) Uani 1 1 d . . . . .
C2 C 0.0807(2) 0.4377(2) 0.7078(6) 0.0670(10) Uani 1 1 d . . . . .
C3 C -0.0352(2) 0.3870(2) 0.6626(6) 0.0714(10) Uani 1 1 d . . . . .
H3 H -0.076243 0.403822 0.770745 0.086 Uiso 1 1 calc R U . . .
C4 C -0.0842(2) 0.31857(19) 0.4751(6) 0.0681(10) Uani 1 1 d . . . . .
C5 C -0.0196(2) 0.2916(2) 0.3026(6) 0.0712(10) Uani 1 1 d . . . . .
C6 C 0.0966(2) 0.3410(3) 0.3516(6) 0.0749(11) Uani 1 1 d . . . . .
H6 H 0.137453 0.322334 0.247835 0.090 Uiso 1 1 calc R U . . .
C7 C 0.2667(2) 0.4697(2) 0.5847(8) 0.0872(12) Uani 1 1 d . . . . .
H7A H 0.300532 0.534656 0.481270 0.105 Uiso 1 1 calc R U . . .
H7B H 0.280473 0.491784 0.761770 0.105 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0895(15) 0.0746(14) 0.0949(18) -0.0267(11) -0.0093(12) 0.0382(11)
O2 0.0970(18) 0.1125(19) 0.0960(19) -0.0313(15) -0.0265(14) 0.0405(13)
C1 0.0587(15) 0.0567(14) 0.0820(19) -0.0046(13) -0.0039(13) 0.0309(12)
C2 0.0705(17) 0.0528(14) 0.080(2) -0.0017(13) -0.0023(14) 0.0327(12)
C3 0.0651(16) 0.0592(15) 0.095(2) -0.0003(14) 0.0076(15) 0.0347(13)
C4 0.0567(15) 0.0541(14) 0.093(2) 0.0141(13) -0.0003(14) 0.0271(12)
C5 0.0687(17) 0.0649(16) 0.0724(18) -0.0061(14) -0.0094(14) 0.0277(13)
C6 0.0646(17) 0.0777(18) 0.082(2) -0.0152(15) -0.0002(14) 0.0356(14)
C7 0.0631(17) 0.0687(18) 0.131(3) -0.0233(17) -0.0132(16) 0.0342(13)

_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 C2 1.238(3) . ?
O2 C5 1.219(3) . ?
C1 C6 1.327(4) . ?
C1 C2 1.463(4) . ?
C1 C7 1.518(4) . ?
C2 C3 1.457(4) . ?
C3 C4 1.316(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.475(4) . ?
C4 C7 1.507(4) 6_556 ?
C5 C6 1.465(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.8(2) . . ?
C6 C1 C7 124.0(3) . . ?
C2 C1 C7 117.1(2) . . ?
O1 C2 C3 120.8(3) . . ?
O1 C2 C1 120.4(2) . . ?
C3 C2 C1 118.8(2) . . ?
C4 C3 C2 122.8(3) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C7 124.9(3) . 6_556 ?
C5 C4 C7 116.2(3) . 6_556 ?
O2 C5 C6 120.6(3) . . ?
O2 C5 C4 121.2(3) . . ?
C6 C5 C4 118.2(3) . . ?
C1 C6 C5 122.5(3) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C4 C7 C1 113.9(2) 5_556 . ?
C4 C7 H7A 108.8 5_556 . ?
C1 C7 H7A 108.8 . . ?
C4 C7 H7B 108.8 5_556 . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 179.6(3) . . . . ?
C7 C1 C2 O1 -2.2(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 C1 C2 C3 177.2(3) . . . . ?
O1 C2 C3 C4 179.3(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C7 -178.0(2) . . . 6_556 ?
C3 C4 C5 O2 -177.7(3) . . . . ?
C7 C4 C5 O2 0.5(4) 6_556 . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C7 C4 C5 C6 179.4(3) 6_556 . . . ?
C2 C1 C6 C5 2.2(4) . . . . ?
C7 C1 C6 C5 -175.8(3) . . . . ?
O2 C5 C6 C1 176.5(3) . . . . ?
C4 C5 C6 C1 -2.4(4) . . . . ?
C6 C1 C7 C4 -35.1(5) . . . 5_556 ?
C2 C1 C7 C4 146.9(3) . . . 5_556 ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.073

_shelx_res_file                  
;

TITL shelxs_a.res in P-3
    shelxl.res
    created by SHELXL-2018/3 at 12:02:54 on 07-Apr-2021
REM Old TITL 190416_uekusa14-4

REM SHELXT solution in P-3
REM R1 0.219,  Rweak 0.023,  Alpha 0.047,  Orientation as input
REM Formula found by SHELXT:  C7 O2

CELL 0.81078 14.28289 14.28289 5.25317 90.00000 90.00000 120.00000
ZERR 1.0 0.00062 0.00062 0.00030 0.00000 0.00000 0.00000
LATT  1
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SFAC C H O
DISP    C     0.00449    0.00219        15.06
DISP    H     0.00000    0.00000         0.67
DISP    O     0.01461    0.00814        45.38
UNIT 42 24 12
L.S. 20
CONF
ACTA
TEMP 0
BOND $H
LIST 6
FMAP 2
PLAN 20
OMIT     0   2   0
OMIT    -4   6   0
WGHT    0.151100    0.059300
EXTI    0.642523
FVAR       1.23843
O1    3    0.123908    0.502535    0.884887    11.00000    0.08951    0.07459 =
         0.09487   -0.02672   -0.00929    0.03820
O2    3   -0.061013    0.231180    0.121758    11.00000    0.09703    0.11250 =
         0.09597   -0.03130   -0.02653    0.04050
C1    1    0.145599    0.411308    0.538567    11.00000    0.05866    0.05672 =
         0.08196   -0.00457   -0.00390    0.03090
C2    1    0.080712    0.437683    0.707785    11.00000    0.07046    0.05282 =
         0.08013   -0.00168   -0.00231    0.03270
C3    1   -0.035178    0.387048    0.662563    11.00000    0.06510    0.05923 =
         0.09479   -0.00029    0.00759    0.03470
AFIX  43
H3    2   -0.076243    0.403822    0.770745    11.00000   -1.20000
AFIX   0
C4    1   -0.084220    0.318567    0.475082    11.00000    0.05669    0.05405 =
         0.09272    0.01407   -0.00026    0.02710
C5    1   -0.019646    0.291561    0.302635    11.00000    0.06874    0.06491 =
         0.07245   -0.00615   -0.00938    0.02774
C6    1    0.096558    0.340973    0.351639    11.00000    0.06461    0.07770 =
         0.08238   -0.01518   -0.00022    0.03560
AFIX  43
H6    2    0.137453    0.322334    0.247835    11.00000   -1.20000
AFIX   0
C7    1    0.266704    0.469722    0.584734    11.00000    0.06310    0.06874 =
         0.13132   -0.02334   -0.01322    0.03423
AFIX  23
H7A   2    0.300532    0.534656    0.481270    11.00000   -1.20000
H7B   2    0.280473    0.491784    0.761770    11.00000   -1.20000
AFIX   0
HKLF 4




REM  shelxs_a.res in P-3
REM wR2 = 0.2585, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0864 for 775 Fo > 4sig(Fo) and 0.1055 for all 1111 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.1511      0.0593

REM Highest difference peak  0.390,  deepest hole -0.217,  1-sigma level  0.073
Q1    1   0.0000  0.0000  0.0986  10.33333  0.05    0.39
Q2    1   0.0000  0.0000  0.3079  10.33333  0.05    0.39
Q3    1   0.1895  0.4396  0.5766  11.00000  0.05    0.23
Q4    1   0.1393  0.3711  0.5008  11.00000  0.05    0.22
Q5    1   0.3333  0.6667  0.1442  10.33333  0.05    0.22
Q6    1   0.0983  0.3774  0.6228  11.00000  0.05    0.20
Q7    1   0.3333  0.6667  0.8371  10.33333  0.05    0.19
Q8    1   0.0401  0.3389  0.2898  11.00000  0.05    0.18
Q9    1   0.1383  0.5179  0.4188  11.00000  0.05    0.17
Q10   1   0.1445  0.3679  0.1056  11.00000  0.05    0.17
Q11   1  -0.0771  0.2676  0.3538  11.00000  0.05    0.16
Q12   1  -0.0818  0.1546  0.1498  11.00000  0.05    0.16
Q13   1   0.1042  0.4221  0.4417  11.00000  0.05    0.14
Q14   1  -0.0419  0.3627  0.1815  11.00000  0.05    0.14
Q15   1   0.1882  0.5178  0.6967  11.00000  0.05    0.13
Q16   1  -0.1538  0.1586  0.0759  11.00000  0.05    0.12
Q17   1   0.0006  0.1537  0.0240  11.00000  0.05    0.12
Q18   1   0.0566  0.4832  0.9321  11.00000  0.05    0.12
Q19   1   0.1223  0.3045  0.5850  11.00000  0.05    0.11
Q20   1   0.0595  0.3278  0.7749  11.00000  0.05    0.11
;
_shelx_res_checksum              38252
