# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2216887'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT355_K5-30               
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O2       - H2       .       1.09 Ang.  
RESPONSE: H2 is in a quite short hydrogen bond.
;
_vrf_PLAT772_K5-30               
;
PROBLEM: Suspect O-H Bond in CIF: O3       --H2        ..       1.47 Ang.  
RESPONSE: H2 is in a quite short hydrogen bond.
;
# 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          ?
_chemical_formula_moiety         'C18 H10 O4'
_chemical_formula_sum            'C18 H10 O4'
_chemical_formula_weight         290.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.67957(9)
_cell_length_b                   12.2687(2)
_cell_length_c                   27.5101(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1241.90(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    89.8(4)
_cell_measurement_reflns_used    23423
_cell_measurement_theta_min      1.8100
_cell_measurement_theta_max      41.8150

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.0020
0 1 -1 0.0090
2 0 1 0.0879
-2 0 -1 0.0869
0 2 -1 0.0090
0 1 0 0.0100
0 -2 -1 0.0060
0 2 1 0.0110
0 1 2 0.0120
0 -1 -2 0.0080
0 0 -1 0.0070
0 0 1 0.0130

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
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   ?
_diffrn_ambient_temperature      89.8(4)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-11 with HyPix6000HE'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            111573
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_theta_min         1.817
_diffrn_reflns_theta_max         45.233
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10297
_reflns_number_gt                8558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0562P)²+0.0380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10297
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
O2 O 0.5936(2) 0.28695(5) 0.67601(2) 0.01628(11) Uani 1 1 d . . . . .
H2 H 0.700(10) 0.284(2) 0.6392(9) 0.096(9) Uiso 1 1 d . . . . .
O3 O 0.7923(2) 0.30164(5) 0.58777(2) 0.01560(11) Uani 1 1 d . . . . .
O4 O 0.3864(2) 0.66956(5) 0.58189(2) 0.01570(11) Uani 1 1 d . . . . .
H1 H 0.296(8) 0.6720(19) 0.6189(8) 0.076(8) Uiso 1 1 d . . . . .
O1 O 0.1721(2) 0.65301(5) 0.66886(2) 0.01530(10) Uani 1 1 d . . . . .
C1 C 0.4298(2) 0.47336(6) 0.65400(2) 0.01077(10) Uani 1 1 d . . . . .
C7 C 0.3103(2) 0.34977(7) 0.77621(3) 0.01438(12) Uani 1 1 d . . . . .
H7 H 0.394570 0.276615 0.777213 0.017 Uiso 1 1 calc R U . . .
C8 C 0.3226(2) 0.41008(6) 0.73401(3) 0.01197(11) Uani 1 1 d . . . . .
C9 C 0.4623(2) 0.38331(6) 0.68497(3) 0.01176(11) Uani 1 1 d . . . . .
C10 C 0.5437(2) 0.48205(6) 0.60329(2) 0.01069(10) Uani 1 1 d . . . . .
C11 C 0.7117(2) 0.39662(6) 0.57474(3) 0.01171(10) Uani 1 1 d . . . . .
C12 C 0.7806(2) 0.43885(6) 0.52487(3) 0.01194(11) Uani 1 1 d . . . . .
C13 C 0.9250(2) 0.38901(7) 0.48434(3) 0.01397(12) Uani 1 1 d . . . . .
H13 H 1.003252 0.315241 0.485189 0.017 Uiso 1 1 calc R U . . .
C14 C 0.9519(2) 0.45174(7) 0.44159(3) 0.01520(12) Uani 1 1 d . . . . .
H14 H 1.049290 0.419809 0.412953 0.018 Uiso 1 1 calc R U . . .
C15 C 0.8380(2) 0.55957(7) 0.44077(3) 0.01531(12) Uani 1 1 d . . . . .
H15 H 0.860391 0.600382 0.411576 0.018 Uiso 1 1 calc R U . . .
C16 C 0.6898(2) 0.60972(6) 0.48233(3) 0.01391(12) Uani 1 1 d . . . . .
H16 H 0.611407 0.683478 0.481762 0.017 Uiso 1 1 calc R U . . .
C17 C 0.6632(2) 0.54745(6) 0.52387(3) 0.01168(11) Uani 1 1 d . . . . .
C18 C 0.5171(2) 0.57315(6) 0.57264(3) 0.01149(11) Uani 1 1 d . . . . .
C2 C 0.2596(2) 0.55873(6) 0.68235(3) 0.01140(10) Uani 1 1 d . . . . .
C3 C 0.1984(2) 0.51802(6) 0.73252(3) 0.01177(10) Uani 1 1 d . . . . .
C4 C 0.0610(2) 0.56926(7) 0.77313(3) 0.01395(12) Uani 1 1 d . . . . .
H4 H -0.020748 0.642660 0.771952 0.017 Uiso 1 1 calc R U . . .
C5 C 0.0467(2) 0.50823(7) 0.81648(3) 0.01561(13) Uani 1 1 d . . . . .
H5 H -0.046885 0.540893 0.845182 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1673(2) 0.40120(7) 0.81787(3) 0.01584(12) Uani 1 1 d . . . . .
H6 H 0.153291 0.361692 0.847505 0.019 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
O2 C9 1.3006(9) . ?
O2 H2 1.09(3) . ?
O3 C11 1.2549(9) . ?
O3 H2 1.47(2) . ?
O4 C18 1.3019(9) . ?
O4 H1 1.07(2) . ?
O1 C2 1.2567(9) . ?
O1 H1 1.47(2) . ?
C1 C9 1.4003(10) . ?
C1 C2 1.4482(10) . ?
C1 C10 1.4606(9) . ?
C7 C8 1.3774(10) . ?
C7 C6 1.4099(11) . ?
C7 H7 0.9500 . ?
C8 C3 1.4016(11) . ?
C8 C9 1.4808(10) . ?
C10 C18 1.4033(10) . ?
C10 C11 1.4482(10) . ?
C11 C12 1.4882(10) . ?
C12 C13 1.3781(10) . ?
C12 C17 1.4010(10) . ?
C13 C14 1.4089(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.3880(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.4082(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.3779(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.4795(10) . ?
C2 C3 1.4851(10) . ?
C3 C4 1.3780(10) . ?
C4 C5 1.4091(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.3865(12) . ?
C5 H5 0.9500 . ?
C6 H6 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
C9 O2 H2 109.8(15) . . ?
C11 O3 H2 110.8(11) . . ?
C18 O4 H1 109.0(13) . . ?
C2 O1 H1 110.1(10) . . ?
C9 C1 C2 106.26(6) . . ?
C9 C1 C10 127.89(6) . . ?
C2 C1 C10 125.84(6) . . ?
C8 C7 C6 117.18(8) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C3 121.43(7) . . ?
C7 C8 C9 131.32(7) . . ?
C3 C8 C9 107.23(6) . . ?
O2 C9 C1 129.32(7) . . ?
O2 C9 C8 120.21(6) . . ?
C1 C9 C8 110.47(6) . . ?
C18 C10 C11 106.28(6) . . ?
C18 C10 C1 127.73(6) . . ?
C11 C10 C1 125.99(6) . . ?
O3 C11 C10 128.18(7) . . ?
O3 C11 C12 123.11(7) . . ?
C10 C11 C12 108.71(6) . . ?
C13 C12 C17 121.67(7) . . ?
C13 C12 C11 131.08(7) . . ?
C17 C12 C11 107.25(6) . . ?
C12 C13 C14 117.39(7) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
C15 C14 C13 120.86(7) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.34(7) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 117.30(7) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C12 121.44(7) . . ?
C16 C17 C18 131.28(7) . . ?
C12 C17 C18 107.27(6) . . ?
O4 C18 C10 129.20(7) . . ?
O4 C18 C17 120.33(6) . . ?
C10 C18 C17 110.47(6) . . ?
O1 C2 C1 128.14(7) . . ?
O1 C2 C3 123.02(7) . . ?
C1 C2 C3 108.84(6) . . ?
C4 C3 C8 121.80(7) . . ?
C4 C3 C2 130.98(7) . . ?
C8 C3 C2 107.18(6) . . ?
C3 C4 C5 117.22(7) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 120.96(7) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.40(7) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?

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 C7 C8 C3 0.01(12) . . . . ?
C6 C7 C8 C9 178.06(8) . . . . ?
C2 C1 C9 O2 179.01(8) . . . . ?
C10 C1 C9 O2 -1.27(14) . . . . ?
C2 C1 C9 C8 -1.46(9) . . . . ?
C10 C1 C9 C8 178.26(7) . . . . ?
C7 C8 C9 O2 2.15(14) . . . . ?
C3 C8 C9 O2 -179.59(8) . . . . ?
C7 C8 C9 C1 -177.43(9) . . . . ?
C3 C8 C9 C1 0.83(9) . . . . ?
C9 C1 C10 C18 -178.64(8) . . . . ?
C2 C1 C10 C18 1.04(12) . . . . ?
C9 C1 C10 C11 0.78(13) . . . . ?
C2 C1 C10 C11 -179.54(8) . . . . ?
C18 C10 C11 O3 178.89(8) . . . . ?
C1 C10 C11 O3 -0.63(14) . . . . ?
C18 C10 C11 C12 -1.05(9) . . . . ?
C1 C10 C11 C12 179.43(7) . . . . ?
O3 C11 C12 C13 1.96(14) . . . . ?
C10 C11 C12 C13 -178.09(8) . . . . ?
O3 C11 C12 C17 -178.87(8) . . . . ?
C10 C11 C12 C17 1.07(9) . . . . ?
C17 C12 C13 C14 0.26(12) . . . . ?
C11 C12 C13 C14 179.32(8) . . . . ?
C12 C13 C14 C15 0.24(13) . . . . ?
C13 C14 C15 C16 -0.43(13) . . . . ?
C14 C15 C16 C17 0.13(13) . . . . ?
C15 C16 C17 C12 0.37(12) . . . . ?
C15 C16 C17 C18 -178.59(8) . . . . ?
C13 C12 C17 C16 -0.57(12) . . . . ?
C11 C12 C17 C16 -179.83(7) . . . . ?
C13 C12 C17 C18 178.61(7) . . . . ?
C11 C12 C17 C18 -0.65(8) . . . . ?
C11 C10 C18 O4 -179.71(8) . . . . ?
C1 C10 C18 O4 -0.20(14) . . . . ?
C11 C10 C18 C17 0.65(9) . . . . ?
C1 C10 C18 C17 -179.84(7) . . . . ?
C16 C17 C18 O4 -0.59(14) . . . . ?
C12 C17 C18 O4 -179.66(7) . . . . ?
C16 C17 C18 C10 179.08(8) . . . . ?
C12 C17 C18 C10 0.01(9) . . . . ?
C9 C1 C2 O1 -178.51(8) . . . . ?
C10 C1 C2 O1 1.75(13) . . . . ?
C9 C1 C2 C3 1.55(9) . . . . ?
C10 C1 C2 C3 -178.18(7) . . . . ?
C7 C8 C3 C4 0.53(12) . . . . ?
C9 C8 C3 C4 -177.94(8) . . . . ?
C7 C8 C3 C2 178.63(8) . . . . ?
C9 C8 C3 C2 0.16(8) . . . . ?
O1 C2 C3 C4 -3.14(14) . . . . ?
C1 C2 C3 C4 176.80(8) . . . . ?
O1 C2 C3 C8 179.00(8) . . . . ?
C1 C2 C3 C8 -1.06(9) . . . . ?
C8 C3 C4 C5 -0.59(12) . . . . ?
C2 C3 C4 C5 -178.18(8) . . . . ?
C3 C4 C5 C6 0.13(13) . . . . ?
C4 C5 C6 C7 0.40(13) . . . . ?
C8 C7 C6 C5 -0.46(13) . . . . ?

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
O2 H2 O3 1.09(3) 1.47(2) 2.5418(9) 167(3) . yes
O4 H1 O1 1.07(2) 1.47(2) 2.5274(8) 169(2) . yes

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2216888'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-10-16 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         'C20 H14 O4'
_chemical_formula_sum            'C20 H14 O4'
_chemical_formula_weight         318.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   3.70624(19)
_cell_length_b                   9.6097(3)
_cell_length_c                   10.9769(4)
_cell_angle_alpha                104.134(3)
_cell_angle_beta                 97.329(4)
_cell_angle_gamma                100.536(3)
_cell_volume                     366.59(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    90.00(10)
_cell_measurement_reflns_used    8330
_cell_measurement_theta_min      1.9210
_cell_measurement_theta_max      29.5730

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 0 0.0090
0 -2 0 0.0150
0 -4 1 0.0140
2 -2 0 0.2194
0 -2 2 0.0160
0 0 -1 0.0100
0 0 1 0.0100
0 -2 -1 0.0160
0 2 1 0.0110
-2 1 1 0.2408

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             166
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
 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   ?
_diffrn_ambient_temperature      90.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-11 with HyPix6000HE'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            24415
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         29.925
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1919
_reflns_number_gt                1637
_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       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0768P)²+0.1271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual-space
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1919
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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 0.5058(3) 0.78845(12) 0.57150(11) 0.0366(3) Uani 1 1 d . . . . .
H1 H 0.444(15) 0.760(6) 0.640(5) 0.055 Uiso 0.455(5) 1 d . U P . .
O2 O 0.6650(3) 0.36116(13) 0.27513(11) 0.0382(3) Uani 1 1 d . . . . .
H2 H 0.602(13) 0.310(5) 0.334(4) 0.057 Uiso 0.545(5) 1 d . U P . .
C1 C 0.5494(4) 0.54291(16) 0.45602(13) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.5699(4) 0.69823(17) 0.47598(14) 0.0329(3) Uani 1 1 d . . . . .
C3 C 0.6760(4) 0.74215(18) 0.36260(14) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.7243(4) 0.87554(19) 0.33478(16) 0.0390(4) Uani 1 1 d . . . . .
H4 H 0.681(6) 0.959(2) 0.397(2) 0.047(5) Uiso 1 1 d . . . . .
C7 C 0.8023(4) 0.6194(2) 0.15769(15) 0.0393(4) Uani 1 1 d . . . . .
H7 H 0.821(6) 0.530(2) 0.100(2) 0.047(5) Uiso 1 1 d . . . . .
C8 C 0.7175(4) 0.61536(18) 0.27532(15) 0.0343(4) Uani 1 1 d . . . . .
C9 C 0.6426(4) 0.49265(17) 0.33429(14) 0.0331(3) Uani 1 1 d . . . . .
C5 C 0.8127(5) 0.8807(2) 0.21490(17) 0.0426(4) Uani 0.545(5) 1 d . . P A 1
H5 H 0.847854 0.971686 0.193505 0.051 Uiso 0.545(5) 1 calc R U P A 1
C6 C 0.8497(5) 0.7549(2) 0.12714(16) 0.0425(4) Uani 0.545(5) 1 d . . P A 1
C10 C 0.9403(9) 0.7788(3) 0.0018(3) 0.0415(8) Uani 0.545(5) 1 d . . P A 1
H10A H 0.714953 0.741386 -0.064275 0.062 Uiso 0.545(5) 1 calc R U P A 1
H10B H 1.133410 0.726316 -0.023856 0.062 Uiso 0.545(5) 1 calc R U P A 1
H10C H 1.030869 0.884258 0.012455 0.062 Uiso 0.545(5) 1 calc R U P A 1
C5' C 0.8127(5) 0.8807(2) 0.21490(17) 0.0426(4) Uani 0.455(5) 1 d . . P A -2
C6' C 0.8497(5) 0.7549(2) 0.12714(16) 0.0425(4) Uani 0.455(5) 1 d . . P A -2
H6' H 0.907041 0.760327 0.046281 0.051 Uiso 0.455(5) 1 calc R U P A -2
C10' C 0.8448(13) 1.0070(4) 0.1707(4) 0.0456(11) Uani 0.455(5) 1 d . . P A -2
H10D H 0.909254 0.984793 0.085229 0.068 Uiso 0.455(5) 1 calc R U P A -2
H10E H 1.040773 1.086351 0.229102 0.068 Uiso 0.455(5) 1 calc R U P A -2
H10F H 0.606806 1.037845 0.166839 0.068 Uiso 0.455(5) 1 calc R U P A -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2659(18) . ?
O1 H1 0.90(6) . ?
O2 C9 1.2948(18) . ?
O2 H2 0.92(5) . ?
C1 C9 1.415(2) . ?
C1 C2 1.441(2) . ?
C1 C1 1.454(3) 2_666 ?
C2 C3 1.484(2) . ?
C3 C4 1.375(2) . ?
C3 C8 1.401(2) . ?
C4 C5' 1.406(2) . ?
C4 C5 1.406(2) . ?
C4 H4 0.97(2) . ?
C7 C8 1.375(2) . ?
C7 C6' 1.408(3) . ?
C7 C6 1.408(3) . ?
C7 H7 0.95(2) . ?
C8 C9 1.478(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C10 1.518(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5' C6' 1.391(2) . ?
C5' C10' 1.404(4) . ?
C6' H6' 0.9500 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 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 122(4) . . ?
C9 O2 H2 101(3) . . ?
C9 C1 C2 105.91(14) . . ?
C9 C1 C1 127.72(16) . 2_666 ?
C2 C1 C1 126.38(16) . 2_666 ?
O1 C2 C1 128.13(16) . . ?
O1 C2 C3 122.57(15) . . ?
C1 C2 C3 109.29(13) . . ?
C4 C3 C8 121.32(16) . . ?
C4 C3 C2 131.44(15) . . ?
C8 C3 C2 107.21(14) . . ?
C3 C4 C5' 117.89(16) . . ?
C3 C4 C5 117.89(16) . . ?
C3 C4 H4 117.9(13) . . ?
C5' C4 H4 124.1(13) . . ?
C5 C4 H4 124.1(13) . . ?
C8 C7 C6' 118.34(16) . . ?
C8 C7 C6 118.34(16) . . ?
C8 C7 H7 118.4(13) . . ?
C6' C7 H7 123.3(13) . . ?
C6 C7 H7 123.3(13) . . ?
C7 C8 C3 121.11(16) . . ?
C7 C8 C9 131.57(15) . . ?
C3 C8 C9 107.29(14) . . ?
O2 C9 C1 128.79(16) . . ?
O2 C9 C8 120.91(14) . . ?
C1 C9 C8 110.30(13) . . ?
C6 C5 C4 121.08(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.24(16) . . ?
C5 C6 C10 114.48(19) . . ?
C7 C6 C10 125.28(18) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6' C5' C10' 114.9(2) . . ?
C6' C5' C4 121.08(17) . . ?
C10' C5' C4 123.9(2) . . ?
C5' C6' C7 120.24(16) . . ?
C5' C6' H6' 119.9 . . ?
C7 C6' H6' 119.9 . . ?
C5' C10' H10D 109.5 . . ?
C5' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C5' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 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
C9 C1 C2 O1 179.36(14) . . . . ?
C1 C1 C2 O1 -0.4(3) 2_666 . . . ?
C9 C1 C2 C3 0.39(15) . . . . ?
C1 C1 C2 C3 -179.33(16) 2_666 . . . ?
O1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 178.66(15) . . . . ?
O1 C2 C3 C8 -178.82(13) . . . . ?
C1 C2 C3 C8 0.22(16) . . . . ?
C8 C3 C4 C5' 0.7(2) . . . . ?
C2 C3 C4 C5' -177.51(14) . . . . ?
C8 C3 C4 C5 0.7(2) . . . . ?
C2 C3 C4 C5 -177.51(14) . . . . ?
C6' C7 C8 C3 0.5(2) . . . . ?
C6 C7 C8 C3 0.5(2) . . . . ?
C6' C7 C8 C9 178.30(14) . . . . ?
C6 C7 C8 C9 178.30(14) . . . . ?
C4 C3 C8 C7 -1.1(2) . . . . ?
C2 C3 C8 C7 177.57(13) . . . . ?
C4 C3 C8 C9 -179.35(13) . . . . ?
C2 C3 C8 C9 -0.71(16) . . . . ?
C2 C1 C9 O2 179.40(14) . . . . ?
C1 C1 C9 O2 -0.9(3) 2_666 . . . ?
C2 C1 C9 C8 -0.84(16) . . . . ?
C1 C1 C9 C8 178.87(17) 2_666 . . . ?
C7 C8 C9 O2 2.7(3) . . . . ?
C3 C8 C9 O2 -179.22(12) . . . . ?
C7 C8 C9 C1 -177.04(15) . . . . ?
C3 C8 C9 C1 1.00(17) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C10 179.17(18) . . . . ?
C8 C7 C6 C5 0.3(2) . . . . ?
C8 C7 C6 C10 -179.45(19) . . . . ?
C3 C4 C5' C6' 0.1(2) . . . . ?
C3 C4 C5' C10' 175.5(3) . . . . ?
C10' C5' C6' C7 -176.5(2) . . . . ?
C4 C5' C6' C7 -0.6(3) . . . . ?
C8 C7 C6' C5' 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.90(6) 1.69(6) 2.5343(18) 155(5) 2_666 yes
O2 H2 O1 0.92(5) 1.61(5) 2.5343(18) 176(5) 2_666 yes

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2216889'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT430_K5-58               
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.61 Ang.  
RESPONSE: The intramolecular O-H...O hydrogen bonds are 
commonly observed in such molecules.
;
# 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          ?
_chemical_formula_moiety         'C18 H6 F4 O4'
_chemical_formula_sum            'C18 H6 F4 O4'
_chemical_formula_weight         362.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.17216(5)
_cell_length_b                   7.93147(8)
_cell_length_c                   14.13554(14)
_cell_angle_alpha                76.8037(8)
_cell_angle_beta                 82.2893(7)
_cell_angle_gamma                87.7961(7)
_cell_volume                     667.609(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    89.8(4)
_cell_measurement_reflns_used    64362
_cell_measurement_theta_min      1.4550
_cell_measurement_theta_max      61.8220

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.0914
0 1 2 0.0873
1 0 1 0.2210
-1 0 -1 0.2222
0 0 -1 0.0091
0 0 1 0.0091
0 1 -2 0.0704
2 1 -2 0.1846
-1 -2 0 0.1887
0 1 0 0.1094
0 -1 0 0.1176
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
0.0002 -1.0000 -2.0003 -0.1168 -0.0181 0.0312
-0.0002 1.0000 2.0003 0.1168 0.0181 -0.0312
1.0001 0.0002 1.0002 0.0510 0.0075 0.1093
-1.0001 -0.0002 -1.0002 -0.0510 -0.0075 -0.1093
0.0001 0.0000 -1.0001 -0.0307 -0.0420 -0.0004
-0.0001 -0.0000 1.0001 0.0307 0.0420 0.0004
0.0000 1.0001 -1.9999 -0.0058 -0.1498 -0.0329
2.0003 1.0005 -1.9996 0.0350 -0.2188 0.1848
-1.0000 -2.0003 -0.0005 -0.1314 0.1661 -0.0447
-0.0001 1.0001 0.0002 0.0555 -0.0658 -0.0320
0.0001 -1.0001 -0.0002 -0.0555 0.0658 0.0320

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0203690000
_diffrn_orient_matrix_UB_12      0.0554837000
_diffrn_orient_matrix_UB_13      0.0306506000
_diffrn_orient_matrix_UB_21      -0.0344945000
_diffrn_orient_matrix_UB_22      -0.0658231000
_diffrn_orient_matrix_UB_23      0.0419708000
_diffrn_orient_matrix_UB_31      0.1088330000
_diffrn_orient_matrix_UB_32      -0.0320408000
_diffrn_orient_matrix_UB_33      0.0004280000
_diffrn_measurement_details      
;
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      89.8(4)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-11 with Hypix6000HE'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            19889
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.492
_diffrn_reflns_theta_max         60.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             19889
_reflns_number_gt                16606
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0772P)²+0.0877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         19889
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
F1 F -0.15139(5) 0.56472(4) 0.84222(2) 0.01594(4) Uani 1 1 d . . . . .
F2 F 0.64139(5) 0.22977(4) 0.85045(2) 0.01591(4) Uani 1 1 d . . . . .
F3 F 0.32077(7) 0.15005(5) 1.00220(2) 0.02012(6) Uani 1 1 d . . . . .
F4 F -0.07198(6) 0.31351(5) 0.99806(2) 0.01863(5) Uani 1 1 d . . . . .
O1 O 0.86669(5) 0.63195(4) 0.48275(2) 0.01385(4) Uani 1 1 d . . . . .
O2 O 0.18323(5) 0.92565(4) 0.46825(2) 0.01368(4) Uani 1 1 d . . . . .
H2H H 0.115(3) 0.866(2) 0.5337(13) 0.040(4) Uiso 1 1 d . . . . .
O3 O 0.05815(5) 0.74801(4) 0.64142(2) 0.01311(4) Uani 1 1 d . . . . .
O4 O 0.73971(5) 0.44623(4) 0.65205(2) 0.01302(4) Uani 1 1 d . . . . .
H4H H 0.801(3) 0.510(2) 0.5866(14) 0.048(5) Uiso 1 1 d . . . . .
C1 C 0.49613(6) 0.73820(4) 0.51202(3) 0.01005(4) Uani 1 1 d . . . . .
C2 C 0.71234(6) 0.72751(4) 0.45691(3) 0.01052(4) Uani 1 1 d . . . . .
C3 C 0.71986(6) 0.85287(5) 0.36059(3) 0.01083(4) Uani 1 1 d . . . . .
C4 C 0.88556(7) 0.89084(5) 0.28325(3) 0.01279(5) Uani 1 1 d . . . . .
H4 H 1.024449 0.835319 0.286074 0.015 Uiso 1 1 calc R U . . .
C5 C 0.83942(8) 1.01552(6) 0.20005(3) 0.01421(5) Uani 1 1 d . . . . .
H5 H 0.949229 1.045189 0.145272 0.017 Uiso 1 1 calc R U . . .
C6 C 0.63469(8) 1.09628(6) 0.19677(3) 0.01423(5) Uani 1 1 d . . . . .
H6 H 0.607382 1.179184 0.139427 0.017 Uiso 1 1 calc R U . . .
C7 C 0.46758(7) 1.05752(5) 0.27668(3) 0.01297(5) Uani 1 1 d . . . . .
H7 H 0.328660 1.113188 0.274813 0.016 Uiso 1 1 calc R U . . .
C8 C 0.51528(6) 0.93473(5) 0.35788(3) 0.01085(4) Uani 1 1 d . . . . .
C9 C 0.38080(6) 0.86433(5) 0.45245(3) 0.01044(4) Uani 1 1 d . . . . .
C10 C 0.42630(6) 0.63542(4) 0.60990(3) 0.01014(4) Uani 1 1 d . . . . .
C11 C 0.21150(6) 0.65069(5) 0.66568(3) 0.01036(4) Uani 1 1 d . . . . .
C12 C 0.20437(6) 0.52397(5) 0.76189(3) 0.01098(4) Uani 1 1 d . . . . .
C13 C 0.04267(7) 0.48439(5) 0.83972(3) 0.01222(5) Uani 1 1 d . . . . .
C14 C 0.08379(7) 0.35519(6) 0.92147(3) 0.01369(5) Uani 1 1 d . . . . .
C15 C 0.28474(7) 0.27217(6) 0.92380(3) 0.01400(5) Uani 1 1 d . . . . .
C16 C 0.45067(7) 0.31440(5) 0.84397(3) 0.01222(5) Uani 1 1 d . . . . .
C17 C 0.40831(6) 0.43882(5) 0.76343(3) 0.01082(4) Uani 1 1 d . . . . .
C18 C 0.54247(6) 0.50893(4) 0.66848(3) 0.01034(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
F1 C13 1.3349(5) . ?
F2 C16 1.3359(5) . ?
F3 C15 1.3324(5) . ?
F4 C14 1.3370(5) . ?
O1 C2 1.2357(4) . ?
O2 C9 1.3056(5) . ?
O2 H2H 0.985(18) . ?
O3 C11 1.2326(5) . ?
O4 C18 1.3091(5) . ?
O4 H4H 0.980(19) . ?
C1 C9 1.3921(5) . ?
C1 C10 1.4549(5) . ?
C1 C2 1.4620(5) . ?
C2 C3 1.4876(5) . ?
C3 C4 1.3803(5) . ?
C3 C8 1.3986(5) . ?
C4 C5 1.4069(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.3962(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.4098(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.3823(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.4781(5) . ?
C10 C18 1.3896(5) . ?
C10 C11 1.4645(5) . ?
C11 C12 1.4917(5) . ?
C12 C13 1.3699(5) . ?
C12 C17 1.4058(5) . ?
C13 C14 1.4028(6) . ?
C14 C15 1.3824(6) . ?
C15 C16 1.4065(6) . ?
C16 C17 1.3731(5) . ?
C17 C18 1.4807(5) . ?

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
C9 O2 H2H 109.0(10) . . ?
C18 O4 H4H 106.2(11) . . ?
C9 C1 C10 129.15(3) . . ?
C9 C1 C2 106.06(3) . . ?
C10 C1 C2 124.78(3) . . ?
O1 C2 C1 127.61(3) . . ?
O1 C2 C3 123.89(3) . . ?
C1 C2 C3 108.50(3) . . ?
C4 C3 C8 122.17(3) . . ?
C4 C3 C2 130.72(3) . . ?
C8 C3 C2 107.11(3) . . ?
C3 C4 C5 116.97(4) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 C4 120.99(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.45(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 116.90(4) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C8 C3 121.52(3) . . ?
C7 C8 C9 130.98(3) . . ?
C3 C8 C9 107.49(3) . . ?
O2 C9 C1 130.50(3) . . ?
O2 C9 C8 118.68(3) . . ?
C1 C9 C8 110.82(3) . . ?
C18 C10 C1 128.66(3) . . ?
C18 C10 C11 106.97(3) . . ?
C1 C10 C11 124.37(3) . . ?
O3 C11 C10 128.53(3) . . ?
O3 C11 C12 123.60(3) . . ?
C10 C11 C12 107.86(3) . . ?
C13 C12 C17 121.21(3) . . ?
C13 C12 C11 131.58(3) . . ?
C17 C12 C11 107.21(3) . . ?
F1 C13 C12 123.16(4) . . ?
F1 C13 C14 118.28(3) . . ?
C12 C13 C14 118.55(4) . . ?
F4 C14 C15 119.84(4) . . ?
F4 C14 C13 119.65(4) . . ?
C15 C14 C13 120.50(4) . . ?
F3 C15 C14 119.60(4) . . ?
F3 C15 C16 119.74(4) . . ?
C14 C15 C16 120.65(4) . . ?
F2 C16 C17 123.44(4) . . ?
F2 C16 C15 117.94(3) . . ?
C17 C16 C15 118.61(4) . . ?
C16 C17 C12 120.45(3) . . ?
C16 C17 C18 131.97(3) . . ?
C12 C17 C18 107.57(3) . . ?
O4 C18 C10 130.89(3) . . ?
O4 C18 C17 118.72(3) . . ?
C10 C18 C17 110.39(3) . . ?

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
C9 C1 C2 O1 179.88(4) . . . . ?
C10 C1 C2 O1 0.56(6) . . . . ?
C9 C1 C2 C3 -0.54(4) . . . . ?
C10 C1 C2 C3 -179.87(3) . . . . ?
O1 C2 C3 C4 -0.20(7) . . . . ?
C1 C2 C3 C4 -179.79(4) . . . . ?
O1 C2 C3 C8 179.22(4) . . . . ?
C1 C2 C3 C8 -0.38(4) . . . . ?
C8 C3 C4 C5 -0.63(6) . . . . ?
C2 C3 C4 C5 178.71(4) . . . . ?
C3 C4 C5 C6 0.02(6) . . . . ?
C4 C5 C6 C7 0.62(7) . . . . ?
C5 C6 C7 C8 -0.63(7) . . . . ?
C6 C7 C8 C3 0.02(6) . . . . ?
C6 C7 C8 C9 -179.91(4) . . . . ?
C4 C3 C8 C7 0.62(6) . . . . ?
C2 C3 C8 C7 -178.85(4) . . . . ?
C4 C3 C8 C9 -179.43(4) . . . . ?
C2 C3 C8 C9 1.10(4) . . . . ?
C10 C1 C9 O2 1.09(7) . . . . ?
C2 C1 C9 O2 -178.19(4) . . . . ?
C10 C1 C9 C8 -179.48(4) . . . . ?
C2 C1 C9 C8 1.24(4) . . . . ?
C7 C8 C9 O2 -2.07(7) . . . . ?
C3 C8 C9 O2 177.99(4) . . . . ?
C7 C8 C9 C1 178.43(4) . . . . ?
C3 C8 C9 C1 -1.52(4) . . . . ?
C9 C1 C10 C18 179.53(4) . . . . ?
C2 C1 C10 C18 -1.31(6) . . . . ?
C9 C1 C10 C11 -1.04(6) . . . . ?
C2 C1 C10 C11 178.11(3) . . . . ?
C18 C10 C11 O3 179.60(4) . . . . ?
C1 C10 C11 O3 0.07(6) . . . . ?
C18 C10 C11 C12 -0.40(4) . . . . ?
C1 C10 C11 C12 -179.93(3) . . . . ?
O3 C11 C12 C13 1.00(7) . . . . ?
C10 C11 C12 C13 -179.00(4) . . . . ?
O3 C11 C12 C17 -179.21(4) . . . . ?
C10 C11 C12 C17 0.79(4) . . . . ?
C17 C12 C13 F1 178.44(4) . . . . ?
C11 C12 C13 F1 -1.80(7) . . . . ?
C17 C12 C13 C14 -0.52(6) . . . . ?
C11 C12 C13 C14 179.24(4) . . . . ?
F1 C13 C14 F4 1.42(6) . . . . ?
C12 C13 C14 F4 -179.58(4) . . . . ?
F1 C13 C14 C15 -177.87(4) . . . . ?
C12 C13 C14 C15 1.14(7) . . . . ?
F4 C14 C15 F3 0.58(7) . . . . ?
C13 C14 C15 F3 179.86(4) . . . . ?
F4 C14 C15 C16 -179.93(4) . . . . ?
C13 C14 C15 C16 -0.65(7) . . . . ?
F3 C15 C16 F2 -0.49(7) . . . . ?
C14 C15 C16 F2 -179.98(4) . . . . ?
F3 C15 C16 C17 179.01(4) . . . . ?
C14 C15 C16 C17 -0.48(7) . . . . ?
F2 C16 C17 C12 -179.42(4) . . . . ?
C15 C16 C17 C12 1.10(6) . . . . ?
F2 C16 C17 C18 1.11(7) . . . . ?
C15 C16 C17 C18 -178.37(4) . . . . ?
C13 C12 C17 C16 -0.61(6) . . . . ?
C11 C12 C17 C16 179.57(4) . . . . ?
C13 C12 C17 C18 178.97(4) . . . . ?
C11 C12 C17 C18 -0.84(4) . . . . ?
C1 C10 C18 O4 -1.38(7) . . . . ?
C11 C10 C18 O4 179.12(4) . . . . ?
C1 C10 C18 C17 179.39(4) . . . . ?
C11 C10 C18 C17 -0.11(4) . . . . ?
C16 C17 C18 O4 0.80(7) . . . . ?
C12 C17 C18 O4 -178.72(3) . . . . ?
C16 C17 C18 C10 -179.86(4) . . . . ?
C12 C17 C18 C10 0.62(4) . . . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2216890'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_K5-58-90K           
;
PROBLEM: Short Inter D...A Contact  O2       ..O2       .       2.70 Ang.  
RESPONSE: Due to short intermolecular hydrogen bondings 
neighbouring the O2 atoms.
;
# 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          ?
_chemical_formula_moiety         'C19 H8 F4 O4'
_chemical_formula_sum            'C19 H8 F4 O4'
_chemical_formula_weight         376.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.08386(19)
_cell_length_b                   6.06732(18)
_cell_length_c                   29.2397(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.194(2)
_cell_angle_gamma                90
_cell_volume                     1422.84(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.00(10)
_cell_measurement_reflns_used    12654
_cell_measurement_theta_min      2.5100
_cell_measurement_theta_max      33.4210

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -2 0.0208
-1 0 2 0.0195
0 -2 -1 0.1992
0 2 1 0.2057
1 0 -1 0.0208
2 0 1 0.0208
-2 0 -1 0.0195
1 0 2 0.0195
-1 0 -2 0.0169
0 0 1 0.0092
0 0 -1 0.0092
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
1.0006 0.0001 -2.0030 -0.0706 -0.0641 0.0077
-1.0006 -0.0001 2.0030 0.0706 0.0641 -0.0077
-0.0000 -2.0018 -1.0008 0.0022 0.0116 0.2349
0.0000 2.0018 1.0008 -0.0022 -0.0116 -0.2349
1.0007 0.0001 -1.0021 -0.0485 -0.0743 0.0055
2.0017 0.0002 0.9983 -0.0305 -0.1791 0.0043
-2.0017 -0.0002 -0.9983 0.0305 0.1791 -0.0043
1.0010 0.0001 2.0004 0.0179 -0.1048 -0.0012
-1.0010 -0.0001 -2.0004 -0.0179 0.1048 0.0012
0.0001 0.0000 1.0009 0.0221 -0.0102 -0.0022
-0.0001 -0.0000 -1.0009 -0.0221 0.0102 0.0022

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-11 with Hypix6000HE'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            38918
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3254
_reflns_number_gt                3114
_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       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0112P)²+4.7614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3254
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_restrained_S_all      1.283
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6941(2) 0.7354(3) 0.66403(7) 0.0243(4) Uani 1 1 d . . . . .
F2 F 0.7444(2) 0.4591(4) 0.73615(7) 0.0299(5) Uani 1 1 d . . . . .
F3 F 0.5859(3) 0.0671(4) 0.73538(7) 0.0309(5) Uani 1 1 d . . . . .
F4 F 0.3690(2) -0.0558(3) 0.66182(7) 0.0262(5) Uani 1 1 d . . . . .
O1 O 0.0807(3) 0.1775(4) 0.48534(9) 0.0230(5) Uani 1 1 d . . . . .
H1H H 0.124(5) 0.139(7) 0.5168(15) 0.037(12) Uiso 1 1 d . . . . .
O2 O 0.3710(3) 0.8587(4) 0.49045(8) 0.0224(5) Uani 1 1 d . . . . .
O3 O 0.5192(3) 0.7784(4) 0.57088(8) 0.0202(5) Uani 1 1 d . . . . .
H2H H 0.476(5) 0.822(8) 0.5405(15) 0.042(12) Uiso 1 1 d . . . . .
O4 O 0.2222(3) 0.1006(4) 0.56738(8) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.2575(4) 0.4996(5) 0.50524(11) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.1449(4) 0.3689(5) 0.47759(11) 0.0190(6) Uani 1 1 d . . . . .
C3 C 0.0947(4) 0.4781(6) 0.43271(11) 0.0228(7) Uani 1 1 d . . . . .
C4 C -0.0093(4) 0.4096(7) 0.39453(12) 0.0269(8) Uani 1 1 d . . . . .
H4 H -0.064836 0.271533 0.394194 0.032 Uiso 1 1 calc R U . A 1
C7 C 0.1520(4) 0.8221(7) 0.39648(11) 0.0257(7) Uani 1 1 d . . . . .
H7 H 0.205550 0.961753 0.397435 0.031 Uiso 1 1 calc R U . B 1
C8 C 0.1750(4) 0.6812(6) 0.43333(11) 0.0220(7) Uani 1 1 d . . . . .
C9 C 0.2801(4) 0.6989(5) 0.47886(11) 0.0188(6) Uani 1 1 d . . . . .
C10 C 0.3394(4) 0.4578(5) 0.55174(11) 0.0176(6) Uani 1 1 d . . . . .
C11 C 0.4533(4) 0.5879(5) 0.57892(11) 0.0164(6) Uani 1 1 d . . . . .
C12 C 0.5039(4) 0.4799(5) 0.62376(11) 0.0182(6) Uani 1 1 d . . . . .
C13 C 0.6112(4) 0.5427(5) 0.66145(11) 0.0189(6) Uani 1 1 d . . . . .
C14 C 0.6382(4) 0.4017(6) 0.69926(11) 0.0220(7) Uani 1 1 d . . . . .
C15 C 0.5578(4) 0.2008(6) 0.69891(11) 0.0216(7) Uani 1 1 d . . . . .
C16 C 0.4464(4) 0.1381(5) 0.66055(11) 0.0197(6) Uani 1 1 d . . . . .
C17 C 0.4212(4) 0.2783(5) 0.62370(11) 0.0186(6) Uani 1 1 d . . . . .
C18 C 0.3138(4) 0.2585(5) 0.57824(11) 0.0174(6) Uani 1 1 d . . . . .
C5 C -0.0309(4) 0.5498(7) 0.35603(11) 0.0308(9) Uani 0.525(6) 1 d D . P C 1
C6 C 0.0469(4) 0.7533(7) 0.35731(11) 0.0289(8) Uani 0.525(6) 1 d . . P C 1
H6 H 0.028701 0.847775 0.331260 0.035 Uiso 0.525(6) 1 calc R U P C 1
C19 C -0.1252(7) 0.4995(11) 0.31115(18) 0.0243(10) Uani 0.525(6) 1 d D . P C 1
H19A H -0.144850 0.635660 0.293280 0.036 Uiso 0.525(6) 1 calc R U P C 1
H19B H -0.232371 0.432919 0.315733 0.036 Uiso 0.525(6) 1 calc R U P C 1
H19C H -0.061527 0.396142 0.294421 0.036 Uiso 0.525(6) 1 calc R U P C 1
C5' C -0.0309(4) 0.5498(7) 0.35603(11) 0.0308(9) Uani 0.475(6) 1 d . . P C -2
H5' H -0.099408 0.504529 0.328882 0.037 Uiso 0.475(6) 1 calc R U P C -2
C6' C 0.0469(4) 0.7533(7) 0.35731(11) 0.0289(8) Uani 0.475(6) 1 d D . P C -2
C19' C 0.0041(8) 0.8767(12) 0.3144(2) 0.0243(10) Uani 0.475(6) 1 d D . P C -2
H19D H 0.106158 0.934214 0.303891 0.036 Uiso 0.475(6) 1 calc R U P C -2
H19E H -0.069659 0.999582 0.319846 0.036 Uiso 0.475(6) 1 calc R U P C -2
H19F H -0.052745 0.778923 0.290809 0.036 Uiso 0.475(6) 1 calc R U P C -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.344(4) . ?
F2 C14 1.337(4) . ?
F3 C15 1.337(4) . ?
F4 C16 1.336(4) . ?
O1 C2 1.303(4) . ?
O1 H1H 0.97(4) . ?
O2 C9 1.238(4) . ?
O3 C11 1.306(4) . ?
O3 H2H 0.95(5) . ?
O4 C18 1.228(4) . ?
C1 C2 1.388(4) . ?
C1 C10 1.458(4) . ?
C1 C9 1.458(4) . ?
C2 C3 1.481(5) . ?
C3 C4 1.375(5) . ?
C3 C8 1.392(5) . ?
C4 C5' 1.404(5) . ?
C4 C5 1.404(5) . ?
C4 H4 0.9500 . ?
C7 C8 1.370(5) . ?
C7 C6' 1.402(5) . ?
C7 C6 1.402(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.491(4) . ?
C10 C11 1.385(4) . ?
C10 C18 1.465(4) . ?
C11 C12 1.477(4) . ?
C12 C13 1.369(4) . ?
C12 C17 1.393(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.381(5) . ?
C15 C16 1.400(5) . ?
C16 C17 1.368(4) . ?
C17 C18 1.499(4) . ?
C5 C6 1.384(6) . ?
C5 C19 1.465(5) . ?
C6 H6 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5' C6' 1.384(6) . ?
C5' H5' 0.9500 . ?
C6' C19' 1.465(5) . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 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 H1H 106(3) . . ?
C11 O3 H2H 108(3) . . ?
C2 C1 C10 129.2(3) . . ?
C2 C1 C9 106.4(3) . . ?
C10 C1 C9 124.4(3) . . ?
O1 C2 C1 130.9(3) . . ?
O1 C2 C3 118.8(3) . . ?
C1 C2 C3 110.3(3) . . ?
C4 C3 C8 121.0(3) . . ?
C4 C3 C2 131.0(4) . . ?
C8 C3 C2 108.0(3) . . ?
C3 C4 C5' 118.0(4) . . ?
C3 C4 C5 118.0(4) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C8 C7 C6' 117.7(4) . . ?
C8 C7 C6 117.7(4) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C3 121.7(3) . . ?
C7 C8 C9 131.6(3) . . ?
C3 C8 C9 106.7(3) . . ?
O2 C9 C1 127.9(3) . . ?
O2 C9 C8 123.6(3) . . ?
C1 C9 C8 108.5(3) . . ?
C11 C10 C1 128.9(3) . . ?
C11 C10 C18 107.1(3) . . ?
C1 C10 C18 124.0(3) . . ?
O3 C11 C10 131.1(3) . . ?
O3 C11 C12 118.6(3) . . ?
C10 C11 C12 110.3(3) . . ?
C13 C12 C17 120.1(3) . . ?
C13 C12 C11 131.9(3) . . ?
C17 C12 C11 108.0(3) . . ?
F1 C13 C12 123.3(3) . . ?
F1 C13 C14 117.5(3) . . ?
C12 C13 C14 119.2(3) . . ?
F2 C14 C15 119.3(3) . . ?
F2 C14 C13 120.1(3) . . ?
C15 C14 C13 120.6(3) . . ?
F3 C15 C14 119.8(3) . . ?
F3 C15 C16 120.1(3) . . ?
C14 C15 C16 120.1(3) . . ?
F4 C16 C17 123.1(3) . . ?
F4 C16 C15 118.3(3) . . ?
C17 C16 C15 118.6(3) . . ?
C16 C17 C12 121.4(3) . . ?
C16 C17 C18 131.4(3) . . ?
C12 C17 C18 107.2(3) . . ?
O4 C18 C10 128.9(3) . . ?
O4 C18 C17 123.7(3) . . ?
C10 C18 C17 107.4(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 C19 113.2(4) . . ?
C4 C5 C19 126.2(4) . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6' C5' C4 120.6(3) . . ?
C6' C5' H5' 119.7 . . ?
C4 C5' H5' 119.7 . . ?
C5' C6' C7 121.0(3) . . ?
C5' C6' C19' 112.0(4) . . ?
C7 C6' C19' 127.0(5) . . ?
C6' C19' H19D 109.5 . . ?
C6' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C6' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 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
C10 C1 C2 O1 0.8(5) . . . . ?
C9 C1 C2 O1 -178.4(3) . . . . ?
C10 C1 C2 C3 -179.9(3) . . . . ?
C9 C1 C2 C3 1.0(3) . . . . ?
O1 C2 C3 C4 -2.5(5) . . . . ?
C1 C2 C3 C4 178.0(3) . . . . ?
O1 C2 C3 C8 178.1(3) . . . . ?
C1 C2 C3 C8 -1.3(3) . . . . ?
C8 C3 C4 C5' 0.5(5) . . . . ?
C2 C3 C4 C5' -178.8(3) . . . . ?
C8 C3 C4 C5 0.5(5) . . . . ?
C2 C3 C4 C5 -178.8(3) . . . . ?
C6' C7 C8 C3 -1.3(5) . . . . ?
C6 C7 C8 C3 -1.3(5) . . . . ?
C6' C7 C8 C9 178.0(3) . . . . ?
C6 C7 C8 C9 178.0(3) . . . . ?
C4 C3 C8 C7 1.1(5) . . . . ?
C2 C3 C8 C7 -179.5(3) . . . . ?
C4 C3 C8 C9 -178.4(3) . . . . ?
C2 C3 C8 C9 1.1(3) . . . . ?
C2 C1 C9 O2 -179.4(3) . . . . ?
C10 C1 C9 O2 1.4(5) . . . . ?
C2 C1 C9 C8 -0.3(3) . . . . ?
C10 C1 C9 C8 -179.5(3) . . . . ?
C7 C8 C9 O2 -0.7(5) . . . . ?
C3 C8 C9 O2 178.6(3) . . . . ?
C7 C8 C9 C1 -179.9(3) . . . . ?
C3 C8 C9 C1 -0.5(3) . . . . ?
C2 C1 C10 C11 179.1(3) . . . . ?
C9 C1 C10 C11 -1.9(5) . . . . ?
C2 C1 C10 C18 0.0(5) . . . . ?
C9 C1 C10 C18 179.0(3) . . . . ?
C1 C10 C11 O3 -0.6(5) . . . . ?
C18 C10 C11 O3 178.6(3) . . . . ?
C1 C10 C11 C12 -179.8(3) . . . . ?
C18 C10 C11 C12 -0.6(3) . . . . ?
O3 C11 C12 C13 1.0(5) . . . . ?
C10 C11 C12 C13 -179.7(3) . . . . ?
O3 C11 C12 C17 -178.4(3) . . . . ?
C10 C11 C12 C17 0.9(3) . . . . ?
C17 C12 C13 F1 -179.4(3) . . . . ?
C11 C12 C13 F1 1.2(5) . . . . ?
C17 C12 C13 C14 0.9(4) . . . . ?
C11 C12 C13 C14 -178.4(3) . . . . ?
F1 C13 C14 F2 -0.6(4) . . . . ?
C12 C13 C14 F2 179.1(3) . . . . ?
F1 C13 C14 C15 -179.8(3) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
F2 C14 C15 F3 0.4(5) . . . . ?
C13 C14 C15 F3 179.6(3) . . . . ?
F2 C14 C15 C16 -179.9(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
F3 C15 C16 F4 0.8(4) . . . . ?
C14 C15 C16 F4 -178.9(3) . . . . ?
F3 C15 C16 C17 -179.6(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
F4 C16 C17 C12 179.7(3) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
F4 C16 C17 C18 -1.2(5) . . . . ?
C15 C16 C17 C18 179.2(3) . . . . ?
C13 C12 C17 C16 -1.0(5) . . . . ?
C11 C12 C17 C16 178.5(3) . . . . ?
C13 C12 C17 C18 179.7(3) . . . . ?
C11 C12 C17 C18 -0.8(3) . . . . ?
C11 C10 C18 O4 179.3(3) . . . . ?
C1 C10 C18 O4 -1.4(5) . . . . ?
C11 C10 C18 C17 0.1(3) . . . . ?
C1 C10 C18 C17 179.4(3) . . . . ?
C16 C17 C18 O4 2.0(5) . . . . ?
C12 C17 C18 O4 -178.8(3) . . . . ?
C16 C17 C18 C10 -178.7(3) . . . . ?
C12 C17 C18 C10 0.5(3) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C3 C4 C5 C19 174.9(4) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C19 C5 C6 C7 -175.5(4) . . . . ?
C8 C7 C6 C5 0.0(5) . . . . ?
C3 C4 C5' C6' -1.8(5) . . . . ?
C4 C5' C6' C7 1.6(5) . . . . ?
C4 C5' C6' C19' -178.1(4) . . . . ?
C8 C7 C6' C5' 0.0(5) . . . . ?
C8 C7 C6' C19' 179.7(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 H1H O4 0.97(4) 1.61(4) 2.568(3) 170(4) . yes
O3 H2H O2 0.95(5) 1.61(5) 2.549(3) 168(4) . yes
O3 H2H O2 0.95(5) 2.53(5) 3.042(3) 114(3) 3_676 yes

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_KS-44
_database_code_depnum_ccdc_archive 'CCDC 2278636'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2023-07-03 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
3,3?-Dihydroxy-5?-octyl-2-benzo[f]indan-2?-indan-1,1?-dione
_chemical_name_common            C8-BIT
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 O4'
_chemical_formula_sum            'C30 H28 O4'
_chemical_formula_weight         452.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.36368(12)
_cell_length_b                   46.3905(12)
_cell_length_c                   8.9511(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.475(2)
_cell_angle_gamma                90
_cell_volume                     2223.15(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    89.9(5)
_cell_measurement_reflns_used    19035
_cell_measurement_theta_min      1.7340
_cell_measurement_theta_max      29.6970

_exptl_crystal_description       plate
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.089
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0013
-1 -1 -1 0.0989
1 2 1 0.0998
0 2 -1 0.0328
-1 -2 0 0.0981
1 2 0 0.1064
1 1 -2 0.0678
-1 -1 2 0.0638
0 0 1 0.0224
0 1 0 0.0078
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021)
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   ?
_diffrn_ambient_temperature      89.9(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-11 with Hypix-6000HE'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            71518
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_k_max       60
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.756
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5074
_reflns_number_gt                4696
_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       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0262P)²+10.0507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0964
_refine_ls_wR_factor_ref         0.2061
_refine_ls_wR_factor_gt          0.2036
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4535(4) 0.59317(5) 0.3162(3) 0.0175(5) Uani 1 1 d . . . . .
H1H H 0.485(9) 0.5737(11) 0.349(6) 0.039(14) Uiso 1 1 d . . . . .
O2 O 1.1838(4) 0.63895(5) 0.5351(3) 0.0164(5) Uani 1 1 d . . . . .
O3 O 0.5739(4) 0.54733(5) 0.4561(3) 0.0172(5) Uani 1 1 d . . . . .
O4 O 1.3038(4) 0.59294(5) 0.6742(3) 0.0180(5) Uani 1 1 d . . . . .
H4H H 1.271(12) 0.6131(14) 0.629(7) 0.07(2) Uiso 1 1 d . . . . .
C1 C 0.8465(6) 0.60621(7) 0.4536(4) 0.0139(6) Uani 1 1 d . . . . .
C2 C 0.6327(6) 0.61084(7) 0.3555(4) 0.0155(6) Uani 1 1 d . . . . .
C3 C 0.6320(6) 0.64035(7) 0.2956(3) 0.0133(6) Uani 1 1 d . . . . .
C4 C 0.4675(6) 0.65415(7) 0.1998(4) 0.0154(6) Uani 1 1 d . . . . .
H4 H 0.323966 0.644448 0.157558 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5139(6) 0.68364(7) 0.1632(4) 0.0148(6) Uani 1 1 d . . . . .
C6 C 0.3466(6) 0.69946(8) 0.0655(4) 0.0179(7) Uani 1 1 d . . . . .
H6 H 0.201031 0.690307 0.022370 0.021 Uiso 1 1 calc R U . . .
C7 C 0.3919(6) 0.72774(8) 0.0325(4) 0.0185(7) Uani 1 1 d . . . . .
H7 H 0.277477 0.737984 -0.033001 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6068(7) 0.74177(7) 0.0948(4) 0.0191(7) Uani 1 1 d . . . . .
H8 H 0.636250 0.761432 0.071875 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7749(6) 0.72689(7) 0.1893(4) 0.0174(7) Uani 1 1 d . . . . .
H9 H 0.920425 0.736415 0.229916 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7338(6) 0.69792(7) 0.2262(4) 0.0146(6) Uani 1 1 d . . . . .
C11 C 0.9027(6) 0.68222(7) 0.3276(4) 0.0148(6) Uani 1 1 d . . . . .
H11 H 1.047944 0.691276 0.371818 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8515(6) 0.65441(7) 0.3591(4) 0.0147(6) Uani 1 1 d . . . . .
C13 C 0.9825(6) 0.63301(7) 0.4600(4) 0.0145(6) Uani 1 1 d . . . . .
C14 C 0.9137(6) 0.58005(7) 0.5355(3) 0.0133(6) Uani 1 1 d . . . . .
C15 C 0.7743(6) 0.55334(7) 0.5324(3) 0.0140(6) Uani 1 1 d . . . . .
C16 C 0.9047(6) 0.53227(7) 0.6354(3) 0.0148(6) Uani 1 1 d . . . . .
C17 C 0.8443(6) 0.50457(7) 0.6721(3) 0.0136(6) Uani 1 1 d . . . . .
H17 H 0.697705 0.495685 0.628653 0.016 Uiso 1 1 calc R U . . .
C18 C 1.0059(6) 0.48939(7) 0.7769(4) 0.0134(6) Uani 1 1 d . . . . .
C19 C 1.2214(6) 0.50323(7) 0.8362(4) 0.0159(7) Uani 1 1 d . . . . .
H19 H 1.331234 0.493063 0.904775 0.019 Uiso 1 1 calc R U . . .
C20 C 1.2812(6) 0.53174(7) 0.7975(4) 0.0157(6) Uani 1 1 d . . . . .
H20 H 1.427684 0.540883 0.839490 0.019 Uiso 1 1 calc R U . . .
C21 C 1.1204(6) 0.54589(7) 0.6970(4) 0.0141(6) Uani 1 1 d . . . . .
C22 C 1.1246(6) 0.57542(7) 0.6352(3) 0.0134(6) Uani 1 1 d . . . . .
C23 C 0.9387(6) 0.45889(7) 0.8178(4) 0.0141(6) Uani 1 1 d . . . . .
H23A H 0.919154 0.447511 0.724253 0.017 Uiso 1 1 calc R U . . .
H23B H 0.773772 0.459332 0.861821 0.017 Uiso 1 1 calc R U . . .
C24 C 1.1203(6) 0.44292(7) 0.9260(4) 0.0140(6) Uani 1 1 d . . . . .
H24A H 1.141073 0.453936 1.020678 0.017 Uiso 1 1 calc R U . . .
H24B H 1.285355 0.441814 0.882499 0.017 Uiso 1 1 calc R U . . .
C25 C 1.0316(6) 0.41246(7) 0.9601(4) 0.0156(6) Uani 1 1 d . . . . .
H25A H 0.870112 0.413655 1.007673 0.019 Uiso 1 1 calc R U . . .
H25B H 1.003060 0.401777 0.864794 0.019 Uiso 1 1 calc R U . . .
C26 C 1.2171(6) 0.39569(7) 1.0627(4) 0.0149(6) Uani 1 1 d . . . . .
H26A H 1.243850 0.406271 1.158421 0.018 Uiso 1 1 calc R U . . .
H26B H 1.379333 0.394783 1.015710 0.018 Uiso 1 1 calc R U . . .
C27 C 1.1319(6) 0.36501(7) 1.0958(4) 0.0158(7) Uani 1 1 d . . . . .
H27A H 1.107997 0.354290 1.000368 0.019 Uiso 1 1 calc R U . . .
H27B H 0.968620 0.365861 1.141551 0.019 Uiso 1 1 calc R U . . .
C28 C 1.3177(6) 0.34859(7) 1.2008(4) 0.0162(7) Uani 1 1 d . . . . .
H28A H 1.480765 0.347791 1.154688 0.019 Uiso 1 1 calc R U . . .
H28B H 1.342096 0.359442 1.295777 0.019 Uiso 1 1 calc R U . . .
C29 C 1.2366(6) 0.31785(7) 1.2361(4) 0.0174(7) Uani 1 1 d . . . . .
H29A H 1.207475 0.307012 1.141387 0.021 Uiso 1 1 calc R U . . .
H29B H 1.076934 0.318529 1.286034 0.021 Uiso 1 1 calc R U . . .
C30 C 1.4318(7) 0.30196(8) 1.3372(4) 0.0210(7) Uani 1 1 d . . . . .
H30A H 1.587064 0.300142 1.285553 0.031 Uiso 1 1 calc R U . . .
H30B H 1.369313 0.282724 1.360427 0.031 Uiso 1 1 calc R U . . .
H30C H 1.464107 0.312835 1.430179 0.031 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 C2 1.296(4) . ?
O1 H1H 0.96(5) . ?
O2 C13 1.267(4) . ?
O3 C15 1.269(4) . ?
O4 C22 1.291(4) . ?
O4 H4H 1.03(6) . ?
C1 C2 1.418(4) . ?
C1 C13 1.441(5) . ?
C1 C14 1.452(5) . ?
C2 C3 1.470(5) . ?
C3 C4 1.353(4) . ?
C3 C12 1.433(4) . ?
C4 C5 1.432(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(5) . ?
C5 C10 1.438(4) . ?
C6 C7 1.370(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.441(4) . ?
C11 C12 1.352(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.489(5) . ?
C14 C22 1.414(4) . ?
C14 C15 1.447(4) . ?
C15 C16 1.489(4) . ?
C16 C17 1.370(5) . ?
C16 C21 1.402(4) . ?
C17 C18 1.424(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(4) . ?
C18 C23 1.511(5) . ?
C19 C20 1.409(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.478(5) . ?
C23 C24 1.524(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.527(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.526(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.529(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.531(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.530(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.531(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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 H1H 113(3) . . ?
C22 O4 H4H 111(4) . . ?
C2 C1 C13 106.4(3) . . ?
C2 C1 C14 127.3(3) . . ?
C13 C1 C14 126.3(3) . . ?
O1 C2 C1 129.1(3) . . ?
O1 C2 C3 120.3(3) . . ?
C1 C2 C3 110.6(3) . . ?
C4 C3 C12 121.7(3) . . ?
C4 C3 C2 131.2(3) . . ?
C12 C3 C2 107.2(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 C10 118.4(3) . . ?
C4 C5 C10 120.0(3) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 119.0(3) . . ?
C9 C10 C11 122.0(3) . . ?
C5 C10 C11 118.9(3) . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C3 121.6(3) . . ?
C11 C12 C13 131.9(3) . . ?
C3 C12 C13 106.5(3) . . ?
O2 C13 C1 128.5(3) . . ?
O2 C13 C12 122.1(3) . . ?
C1 C13 C12 109.4(3) . . ?
C22 C14 C15 105.9(3) . . ?
C22 C14 C1 127.6(3) . . ?
C15 C14 C1 126.4(3) . . ?
O3 C15 C14 128.2(3) . . ?
O3 C15 C16 122.7(3) . . ?
C14 C15 C16 109.1(3) . . ?
C17 C16 C21 122.0(3) . . ?
C17 C16 C15 130.9(3) . . ?
C21 C16 C15 107.0(3) . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 C23 122.8(3) . . ?
C17 C18 C23 118.5(3) . . ?
C18 C19 C20 122.2(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 117.8(3) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 C22 131.6(3) . . ?
C16 C21 C22 107.6(3) . . ?
O4 C22 C14 129.0(3) . . ?
O4 C22 C21 120.7(3) . . ?
C14 C22 C21 110.3(3) . . ?
C18 C23 C24 117.2(3) . . ?
C18 C23 H23A 108.0 . . ?
C24 C23 H23A 108.0 . . ?
C18 C23 H23B 108.0 . . ?
C24 C23 H23B 108.0 . . ?
H23A C23 H23B 107.2 . . ?
C23 C24 C25 112.4(3) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 113.1(3) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C27 113.5(3) . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 C28 113.0(3) . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
C28 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C27 114.1(3) . . ?
C29 C28 H28A 108.7 . . ?
C27 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 C30 112.2(3) . . ?
C28 C29 H29A 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C13 C1 C2 O1 -179.0(3) . . . . ?
C14 C1 C2 O1 -0.6(6) . . . . ?
C13 C1 C2 C3 1.2(4) . . . . ?
C14 C1 C2 C3 179.6(3) . . . . ?
O1 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
O1 C2 C3 C12 179.9(3) . . . . ?
C1 C2 C3 C12 -0.3(4) . . . . ?
C12 C3 C4 C5 -0.8(5) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C3 C4 C5 C6 -178.9(3) . . . . ?
C3 C4 C5 C10 0.9(5) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
C10 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C8 C9 C10 C5 0.4(5) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C6 C5 C10 C9 0.2(5) . . . . ?
C4 C5 C10 C9 -179.7(3) . . . . ?
C6 C5 C10 C11 178.9(3) . . . . ?
C4 C5 C10 C11 -1.0(5) . . . . ?
C9 C10 C11 C12 179.6(3) . . . . ?
C5 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 C3 -0.8(5) . . . . ?
C10 C11 C12 C13 -178.3(3) . . . . ?
C4 C3 C12 C11 0.8(5) . . . . ?
C2 C3 C12 C11 -178.8(3) . . . . ?
C4 C3 C12 C13 178.8(3) . . . . ?
C2 C3 C12 C13 -0.8(3) . . . . ?
C2 C1 C13 O2 179.2(3) . . . . ?
C14 C1 C13 O2 0.8(6) . . . . ?
C2 C1 C13 C12 -1.7(4) . . . . ?
C14 C1 C13 C12 179.9(3) . . . . ?
C11 C12 C13 O2 -1.5(6) . . . . ?
C3 C12 C13 O2 -179.2(3) . . . . ?
C11 C12 C13 C1 179.3(3) . . . . ?
C3 C12 C13 C1 1.6(4) . . . . ?
C2 C1 C14 C22 -179.0(3) . . . . ?
C13 C1 C14 C22 -0.9(5) . . . . ?
C2 C1 C14 C15 0.2(5) . . . . ?
C13 C1 C14 C15 178.3(3) . . . . ?
C22 C14 C15 O3 -178.6(3) . . . . ?
C1 C14 C15 O3 2.1(5) . . . . ?
C22 C14 C15 C16 0.9(3) . . . . ?
C1 C14 C15 C16 -178.5(3) . . . . ?
O3 C15 C16 C17 -1.7(5) . . . . ?
C14 C15 C16 C17 178.8(3) . . . . ?
O3 C15 C16 C21 178.4(3) . . . . ?
C14 C15 C16 C21 -1.0(4) . . . . ?
C21 C16 C17 C18 0.4(5) . . . . ?
C15 C16 C17 C18 -179.4(3) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C16 C17 C18 C23 179.8(3) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C23 C18 C19 C20 -179.7(3) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C19 C20 C21 C22 178.9(3) . . . . ?
C17 C16 C21 C20 0.1(5) . . . . ?
C15 C16 C21 C20 180.0(3) . . . . ?
C17 C16 C21 C22 -179.1(3) . . . . ?
C15 C16 C21 C22 0.8(3) . . . . ?
C15 C14 C22 O4 179.8(3) . . . . ?
C1 C14 C22 O4 -0.9(6) . . . . ?
C15 C14 C22 C21 -0.4(3) . . . . ?
C1 C14 C22 C21 178.9(3) . . . . ?
C20 C21 C22 O4 0.5(5) . . . . ?
C16 C21 C22 O4 179.6(3) . . . . ?
C20 C21 C22 C14 -179.3(3) . . . . ?
C16 C21 C22 C14 -0.3(4) . . . . ?
C19 C18 C23 C24 -1.3(5) . . . . ?
C17 C18 C23 C24 177.9(3) . . . . ?
C18 C23 C24 C25 179.5(3) . . . . ?
C23 C24 C25 C26 177.4(3) . . . . ?
C24 C25 C26 C27 -179.2(3) . . . . ?
C25 C26 C27 C28 -179.1(3) . . . . ?
C26 C27 C28 C29 179.8(3) . . . . ?
C27 C28 C29 C30 178.1(3) . . . . ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2216891'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-10-16 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         'C18 H2 F8 O4'
_chemical_formula_sum            'C18 H2 F8 O4'
_chemical_formula_weight         434.20

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   27.7976(5)
_cell_length_b                   4.71068(9)
_cell_length_c                   10.7649(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.3435(18)
_cell_angle_gamma                90
_cell_volume                     1386.71(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    89.8(5)
_cell_measurement_reflns_used    21196
_cell_measurement_theta_min      1.4610
_cell_measurement_theta_max      29.8570

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.022

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1010
2 0 -1 0.0130
-2 0 1 0.0150
-2 2 1 0.0923
1 -2 0 0.1009
-1 0 2 0.0150
0 0 -1 0.0130
-1 0 -2 0.0130
1 0 2 0.0150
2 0 1 0.0170
-1 0 0 0.0050
1 0 0 0.0170
2 1 0 0.0876

_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
 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   ?
_diffrn_ambient_temperature      89.8(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC-11 with Hypix6000HE'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            77739
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.489
_diffrn_reflns_theta_max         30.156
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3889
_reflns_number_gt                3214
_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       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0167P)²+6.8578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3889
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.66600(7) 0.9563(4) 0.53396(17) 0.0204(4) Uani 1 1 d . . . . .
F2A F 0.73679(7) 0.7540(5) 0.71588(18) 0.0217(4) Uani 1 1 d . . . . .
F3A F 0.71853(7) 0.3096(4) 0.86259(17) 0.0206(4) Uani 1 1 d . . . . .
F4A F 0.62808(7) 0.0920(4) 0.84086(17) 0.0205(4) Uani 1 1 d . . . . .
O1A O 0.55917(8) 0.8848(5) 0.4235(2) 0.0189(5) Uani 1 1 d . . . . .
O2A O 0.52897(9) 0.1300(5) 0.6935(2) 0.0195(5) Uani 1 1 d . . . . .
H1A H 0.4936(19) 0.091(13) 0.661(5) 0.056(16) Uiso 1 1 d . . . . .
C1A C 0.52517(11) 0.5035(7) 0.5336(3) 0.0165(6) Uani 1 1 d . . . . .
C2A C 0.56277(12) 0.6956(7) 0.5041(3) 0.0162(6) Uani 1 1 d . . . . .
C3A C 0.60914(12) 0.6317(7) 0.5936(3) 0.0165(6) Uani 1 1 d . . . . .
C4A C 0.65511(12) 0.7440(7) 0.6065(3) 0.0168(6) Uani 1 1 d . . . . .
C5A C 0.69226(12) 0.6387(7) 0.6999(3) 0.0175(6) Uani 1 1 d . . . . .
C6A C 0.68258(12) 0.4179(7) 0.7759(3) 0.0179(6) Uani 1 1 d . . . . .
C7A C 0.63545(12) 0.3039(7) 0.7635(3) 0.0170(6) Uani 1 1 d . . . . .
C8A C 0.59926(11) 0.4108(7) 0.6727(3) 0.0158(6) Uani 1 1 d . . . . .
C9A C 0.54701(12) 0.3363(7) 0.6340(3) 0.0167(6) Uani 1 1 d . . . . .
F1B F 0.83127(7) 0.9193(4) 0.37075(17) 0.0213(4) Uani 1 1 d . . . . .
F2B F 0.76030(7) 0.6861(5) 0.47899(18) 0.0223(4) Uani 1 1 d . . . . .
F3B F 0.78126(7) 0.2547(5) 0.64723(18) 0.0230(4) Uani 1 1 d . . . . .
F4B F 0.87298(7) 0.0652(4) 0.71691(18) 0.0223(4) Uani 1 1 d . . . . .
O1B O 0.93949(8) 0.8776(5) 0.3683(2) 0.0195(5) Uani 1 1 d . . . . .
O2B O 0.97225(9) 0.1249(5) 0.6666(2) 0.0199(5) Uani 1 1 d . . . . .
H1B H 1.0086(19) 0.118(12) 0.675(5) 0.051(15) Uiso 1 1 d . . . . .
C1B C 0.97470(11) 0.4986(7) 0.5092(3) 0.0169(6) Uani 1 1 d . . . . .
C2B C 0.93631(12) 0.6869(7) 0.4445(3) 0.0168(6) Uani 1 1 d . . . . .
C3B C 0.88975(12) 0.6107(7) 0.4885(3) 0.0171(6) Uani 1 1 d . . . . .
C4B C 0.84315(12) 0.7101(7) 0.4546(3) 0.0169(6) Uani 1 1 d . . . . .
C5B C 0.80600(12) 0.5907(8) 0.5106(3) 0.0189(6) Uani 1 1 d . . . . .
C6B C 0.81695(12) 0.3735(7) 0.5975(3) 0.0185(6) Uani 1 1 d . . . . .
C7B C 0.86480(12) 0.2750(7) 0.6315(3) 0.0176(6) Uani 1 1 d . . . . .
C8B C 0.90078(12) 0.3911(7) 0.5771(3) 0.0173(6) Uani 1 1 d . . . . .
C9B C 0.95340(12) 0.3268(7) 0.5891(3) 0.0175(6) 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
F1A C4A 1.337(4) . ?
F2A C5A 1.334(4) . ?
F3A C6A 1.340(4) . ?
F4A C7A 1.339(4) . ?
O1A C2A 1.236(4) . ?
O2A C9A 1.312(4) . ?
O2A H1A 1.00(5) . ?
C1A C9A 1.386(4) . ?
C1A C1A 1.456(6) 3_666 ?
C1A C2A 1.460(4) . ?
C2A C3A 1.495(4) . ?
C3A C4A 1.367(4) . ?
C3A C8A 1.403(4) . ?
C4A C5A 1.397(4) . ?
C5A C6A 1.380(5) . ?
C6A C7A 1.400(5) . ?
C7A C8A 1.366(4) . ?
C8A C9A 1.479(4) . ?
F1B C4B 1.337(4) . ?
F2B C5B 1.333(4) . ?
F3B C6B 1.332(4) . ?
F4B C7B 1.341(4) . ?
O1B C2B 1.231(4) . ?
O2B C9B 1.311(4) . ?
O2B H1B 1.00(5) . ?
C1B C9B 1.389(4) . ?
C1B C1B 1.455(6) 3_766 ?
C1B C2B 1.464(4) . ?
C2B C3B 1.499(4) . ?
C3B C4B 1.364(5) . ?
C3B C8B 1.403(4) . ?
C4B C5B 1.403(4) . ?
C5B C6B 1.383(5) . ?
C6B C7B 1.394(5) . ?
C7B C8B 1.361(4) . ?
C8B C9B 1.477(5) . ?

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
C9A O2A H1A 114(3) . . ?
C9A C1A C1A 128.5(4) . 3_666 ?
C9A C1A C2A 107.0(3) . . ?
C1A C1A C2A 124.6(4) 3_666 . ?
O1A C2A C1A 129.0(3) . . ?
O1A C2A C3A 123.3(3) . . ?
C1A C2A C3A 107.7(3) . . ?
C4A C3A C8A 120.4(3) . . ?
C4A C3A C2A 132.1(3) . . ?
C8A C3A C2A 107.5(3) . . ?
F1A C4A C3A 122.4(3) . . ?
F1A C4A C5A 118.1(3) . . ?
C3A C4A C5A 119.5(3) . . ?
F2A C5A C6A 120.4(3) . . ?
F2A C5A C4A 119.8(3) . . ?
C6A C5A C4A 119.8(3) . . ?
F3A C6A C5A 120.0(3) . . ?
F3A C6A C7A 119.3(3) . . ?
C5A C6A C7A 120.8(3) . . ?
F4A C7A C8A 123.0(3) . . ?
F4A C7A C6A 118.1(3) . . ?
C8A C7A C6A 118.9(3) . . ?
C7A C8A C3A 120.5(3) . . ?
C7A C8A C9A 132.3(3) . . ?
C3A C8A C9A 107.1(3) . . ?
O2A C9A C1A 130.5(3) . . ?
O2A C9A C8A 118.7(3) . . ?
C1A C9A C8A 110.8(3) . . ?
C9B O2B H1B 111(3) . . ?
C9B C1B C1B 128.3(4) . 3_766 ?
C9B C1B C2B 107.0(3) . . ?
C1B C1B C2B 124.7(4) 3_766 . ?
O1B C2B C1B 128.7(3) . . ?
O1B C2B C3B 123.7(3) . . ?
C1B C2B C3B 107.6(3) . . ?
C4B C3B C8B 121.0(3) . . ?
C4B C3B C2B 131.7(3) . . ?
C8B C3B C2B 107.2(3) . . ?
F1B C4B C3B 122.7(3) . . ?
F1B C4B C5B 118.3(3) . . ?
C3B C4B C5B 119.0(3) . . ?
F2B C5B C6B 120.4(3) . . ?
F2B C5B C4B 119.8(3) . . ?
C6B C5B C4B 119.8(3) . . ?
F3B C6B C5B 119.6(3) . . ?
F3B C6B C7B 119.9(3) . . ?
C5B C6B C7B 120.5(3) . . ?
F4B C7B C8B 123.0(3) . . ?
F4B C7B C6B 117.5(3) . . ?
C8B C7B C6B 119.5(3) . . ?
C7B C8B C3B 120.1(3) . . ?
C7B C8B C9B 132.3(3) . . ?
C3B C8B C9B 107.6(3) . . ?
O2B C9B C1B 130.6(3) . . ?
O2B C9B C8B 118.8(3) . . ?
C1B C9B C8B 110.6(3) . . ?

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
C9A C1A C2A O1A -178.2(3) . . . . ?
C1A C1A C2A O1A 2.3(6) 3_666 . . . ?
C9A C1A C2A C3A 0.3(3) . . . . ?
C1A C1A C2A C3A -179.2(4) 3_666 . . . ?
O1A C2A C3A C4A -2.4(5) . . . . ?
C1A C2A C3A C4A 179.1(3) . . . . ?
O1A C2A C3A C8A 178.6(3) . . . . ?
C1A C2A C3A C8A 0.0(3) . . . . ?
C8A C3A C4A F1A -179.3(3) . . . . ?
C2A C3A C4A F1A 1.7(5) . . . . ?
C8A C3A C4A C5A -0.5(5) . . . . ?
C2A C3A C4A C5A -179.4(3) . . . . ?
F1A C4A C5A F2A 1.2(4) . . . . ?
C3A C4A C5A F2A -177.7(3) . . . . ?
F1A C4A C5A C6A -179.4(3) . . . . ?
C3A C4A C5A C6A 1.7(5) . . . . ?
F2A C5A C6A F3A -3.0(5) . . . . ?
C4A C5A C6A F3A 177.6(3) . . . . ?
F2A C5A C6A C7A 177.2(3) . . . . ?
C4A C5A C6A C7A -2.2(5) . . . . ?
F3A C6A C7A F4A 1.0(4) . . . . ?
C5A C6A C7A F4A -179.2(3) . . . . ?
F3A C6A C7A C8A -178.4(3) . . . . ?
C5A C6A C7A C8A 1.5(5) . . . . ?
F4A C7A C8A C3A -179.5(3) . . . . ?
C6A C7A C8A C3A -0.2(5) . . . . ?
F4A C7A C8A C9A -0.6(6) . . . . ?
C6A C7A C8A C9A 178.7(3) . . . . ?
C4A C3A C8A C7A -0.3(5) . . . . ?
C2A C3A C8A C7A 178.9(3) . . . . ?
C4A C3A C8A C9A -179.4(3) . . . . ?
C2A C3A C8A C9A -0.2(3) . . . . ?
C1A C1A C9A O2A 0.7(7) 3_666 . . . ?
C2A C1A C9A O2A -178.8(3) . . . . ?
C1A C1A C9A C8A 179.1(4) 3_666 . . . ?
C2A C1A C9A C8A -0.4(4) . . . . ?
C7A C8A C9A O2A 0.0(5) . . . . ?
C3A C8A C9A O2A 179.0(3) . . . . ?
C7A C8A C9A C1A -178.6(3) . . . . ?
C3A C8A C9A C1A 0.4(4) . . . . ?
C9B C1B C2B O1B 177.8(3) . . . . ?
C1B C1B C2B O1B -1.6(6) 3_766 . . . ?
C9B C1B C2B C3B -1.6(3) . . . . ?
C1B C1B C2B C3B 179.0(4) 3_766 . . . ?
O1B C2B C3B C4B 3.8(6) . . . . ?
C1B C2B C3B C4B -176.8(3) . . . . ?
O1B C2B C3B C8B -178.2(3) . . . . ?
C1B C2B C3B C8B 1.2(3) . . . . ?
C8B C3B C4B F1B 179.9(3) . . . . ?
C2B C3B C4B F1B -2.4(5) . . . . ?
C8B C3B C4B C5B 0.4(5) . . . . ?
C2B C3B C4B C5B 178.2(3) . . . . ?
F1B C4B C5B F2B 0.3(5) . . . . ?
C3B C4B C5B F2B 179.7(3) . . . . ?
F1B C4B C5B C6B 179.8(3) . . . . ?
C3B C4B C5B C6B -0.7(5) . . . . ?
F2B C5B C6B F3B 1.7(5) . . . . ?
C4B C5B C6B F3B -177.9(3) . . . . ?
F2B C5B C6B C7B -179.4(3) . . . . ?
C4B C5B C6B C7B 1.0(5) . . . . ?
F3B C6B C7B F4B -1.6(5) . . . . ?
C5B C6B C7B F4B 179.6(3) . . . . ?
F3B C6B C7B C8B 177.8(3) . . . . ?
C5B C6B C7B C8B -1.1(5) . . . . ?
F4B C7B C8B C3B -179.9(3) . . . . ?
C6B C7B C8B C3B 0.8(5) . . . . ?
F4B C7B C8B C9B 2.1(6) . . . . ?
C6B C7B C8B C9B -177.2(3) . . . . ?
C4B C3B C8B C7B -0.5(5) . . . . ?
C2B C3B C8B C7B -178.7(3) . . . . ?
C4B C3B C8B C9B 178.0(3) . . . . ?
C2B C3B C8B C9B -0.3(3) . . . . ?
C1B C1B C9B O2B -0.8(7) 3_766 . . . ?
C2B C1B C9B O2B 179.9(3) . . . . ?
C1B C1B C9B C8B -179.2(4) 3_766 . . . ?
C2B C1B C9B C8B 1.5(4) . . . . ?
C7B C8B C9B O2B -1.2(5) . . . . ?
C3B C8B C9B O2B -179.4(3) . . . . ?
C7B C8B C9B C1B 177.4(3) . . . . ?
C3B C8B C9B C1B -0.7(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
O2A H1A O1A 1.00(5) 1.59(5) 2.547(3) 160(5) 3_666 yes
O2B H1B O1B 1.00(5) 1.59(5) 2.548(3) 158(4) 3_766 yes

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2216892'
loop_
_audit_author_name
_audit_author_address
'Daisuke Hashizume'
;RIKEN Center for Emergent Matter Science (CEMS)
Japan
;
_audit_update_record             
;
2022-11-02 deposited with the CCDC.	2023-10-16 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         'C26 H14 O4'
_chemical_formula_sum            'C26 H14 O4'
_chemical_formula_weight         390.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.99456(7)
_cell_length_b                   6.49263(4)
_cell_length_c                   15.52347(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.1836(8)
_cell_angle_gamma                90
_cell_volume                     878.909(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    89.9(4)
_cell_measurement_reflns_used    66672
_cell_measurement_theta_min      2.2940
_cell_measurement_theta_max      61.9360

_exptl_crystal_description       block
_exptl_crystal_colour            'Metallic Blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_min  0.66866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.4a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      89.9(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       ω-scan
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            142224
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         62.221
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             14123
_reflns_number_gt                12979
_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       'CrysAlisPro 1.171.42.4a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.4a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.4a (Rigaku OD, 2021)'
_computing_structure_solution    SHELXT-2018/2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0620P)²+0.0189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14123
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.002
_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 0.30194(2) 0.66482(2) 0.58750(2) 0.01274(2) Uani 1 1 d . . . . .
H1 H 0.3484(8) 0.5273(12) 0.6144(5) 0.0384(19) Uiso 1 1 d . . . . .
O2 O 0.56985(2) 0.67156(2) 0.35836(2) 0.01237(2) Uani 1 1 d . . . . .
C1 C 0.46139(2) 0.59601(2) 0.48364(2) 0.00859(2) Uani 1 1 d . . . . .
C2 C 0.35551(2) 0.70525(2) 0.51828(2) 0.00915(2) Uani 1 1 d . . . . .
C3 C 0.30384(2) 0.89063(2) 0.46543(2) 0.00931(2) Uani 1 1 d . . . . .
C4 C 0.20120(2) 1.03912(3) 0.47384(2) 0.01050(2) Uani 1 1 d . . . . .
H4 H 0.1481(8) 1.0351(12) 0.5238(5) 0.0315(17) Uiso 1 1 d . . . . .
C5 C 0.17370(2) 1.20445(2) 0.41060(2) 0.01011(2) Uani 1 1 d . . . . .
C6 C 0.06597(2) 1.36024(3) 0.41457(2) 0.01264(2) Uani 1 1 d . . . . .
H6 H 0.0075(7) 1.3492(10) 0.4605(4) 0.0226(14) Uiso 1 1 d . . . . .
C7 C 0.04039(2) 1.52051(3) 0.35413(2) 0.01443(3) Uani 1 1 d . . . . .
H7 H -0.0422(7) 1.6339(11) 0.3540(5) 0.0345(17) Uiso 1 1 d . . . . .
C8 C 0.12248(2) 1.53145(3) 0.28772(2) 0.01421(3) Uani 1 1 d . . . . .
H8 H 0.1050(8) 1.6536(11) 0.2451(5) 0.0354(18) Uiso 1 1 d . . . . .
C9 C 0.22807(2) 1.38015(3) 0.28200(2) 0.01246(2) Uani 1 1 d . . . . .
H9 H 0.2881(8) 1.3824(11) 0.2353(5) 0.0329(17) Uiso 1 1 d . . . . .
C10 C 0.25519(2) 1.21316(2) 0.34240(2) 0.01010(2) Uani 1 1 d . . . . .
C11 C 0.36254(2) 1.05327(3) 0.33629(2) 0.01043(2) Uani 1 1 d . . . . .
H11 H 0.4225(7) 1.0594(12) 0.2887(5) 0.0310(17) Uiso 1 1 d . . . . .
C12 C 0.38300(2) 0.89722(2) 0.39667(2) 0.00933(2) Uani 1 1 d . . . . .
C13 C 0.48299(2) 0.71272(2) 0.40752(2) 0.00912(2) 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 C2 1.30740(19) . ?
O2 C13 1.24750(19) . ?
C1 C2 1.3964(2) . ?
C1 C13 1.4563(2) . ?
C1 C1 1.4566(3) 3_666 ?
C2 C3 1.4666(2) . ?
C3 C4 1.3630(2) . ?
C3 C12 1.4214(2) . ?
C4 C5 1.4346(2) . ?
C5 C6 1.4125(2) . ?
C5 C10 1.4288(2) . ?
C6 C7 1.3821(3) . ?
C7 C8 1.4092(3) . ?
C8 C9 1.3842(3) . ?
C9 C10 1.4150(2) . ?
C10 C11 1.4366(2) . ?
C11 C12 1.3618(2) . ?
C12 C13 1.4825(2) . ?

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 C1 C13 106.697(13) . . ?
C2 C1 C1 127.765(17) . 3_666 ?
C13 C1 C1 125.534(16) . 3_666 ?
O1 C2 C1 129.637(15) . . ?
O1 C2 C3 119.631(14) . . ?
C1 C2 C3 110.731(13) . . ?
C4 C3 C12 121.755(14) . . ?
C4 C3 C2 131.005(14) . . ?
C12 C3 C2 107.240(13) . . ?
C3 C4 C5 118.095(15) . . ?
C6 C5 C10 119.072(15) . . ?
C6 C5 C4 120.735(16) . . ?
C10 C5 C4 120.193(14) . . ?
C7 C6 C5 120.758(18) . . ?
C6 C7 C8 120.305(17) . . ?
C9 C8 C7 120.125(17) . . ?
C8 C9 C10 120.720(18) . . ?
C9 C10 C5 119.004(15) . . ?
C9 C10 C11 121.295(16) . . ?
C5 C10 C11 119.701(14) . . ?
C12 C11 C10 118.149(15) . . ?
C11 C12 C3 122.086(14) . . ?
C11 C12 C13 130.937(14) . . ?
C3 C12 C13 106.974(13) . . ?
O2 C13 C1 127.805(15) . . ?
O2 C13 C12 123.847(14) . . ?
C1 C13 C12 108.346(12) . . ?

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
C13 C1 C2 O1 -178.432(17) . . . . ?
C1 C1 C2 O1 0.85(3) 3_666 . . . ?
C13 C1 C2 C3 1.147(18) . . . . ?
C1 C1 C2 C3 -179.57(2) 3_666 . . . ?
O1 C2 C3 C4 -1.33(3) . . . . ?
C1 C2 C3 C4 179.041(17) . . . . ?
O1 C2 C3 C12 178.612(16) . . . . ?
C1 C2 C3 C12 -1.015(18) . . . . ?
C12 C3 C4 C5 0.27(3) . . . . ?
C2 C3 C4 C5 -179.787(16) . . . . ?
C3 C4 C5 C6 178.486(16) . . . . ?
C3 C4 C5 C10 -1.37(3) . . . . ?
C10 C5 C6 C7 -0.70(3) . . . . ?
C4 C5 C6 C7 179.442(17) . . . . ?
C5 C6 C7 C8 -0.38(3) . . . . ?
C6 C7 C8 C9 0.77(3) . . . . ?
C7 C8 C9 C10 -0.04(3) . . . . ?
C8 C9 C10 C5 -1.03(3) . . . . ?
C8 C9 C10 C11 178.937(17) . . . . ?
C6 C5 C10 C9 1.39(2) . . . . ?
C4 C5 C10 C9 -178.747(16) . . . . ?
C6 C5 C10 C11 -178.579(16) . . . . ?
C4 C5 C10 C11 1.28(2) . . . . ?
C9 C10 C11 C12 179.968(16) . . . . ?
C5 C10 C11 C12 -0.06(2) . . . . ?
C10 C11 C12 C3 -1.06(3) . . . . ?
C10 C11 C12 C13 179.687(16) . . . . ?
C4 C3 C12 C11 0.98(3) . . . . ?
C2 C3 C12 C11 -178.970(16) . . . . ?
C4 C3 C12 C13 -179.609(15) . . . . ?
C2 C3 C12 C13 0.440(17) . . . . ?
C2 C1 C13 O2 178.714(17) . . . . ?
C1 C1 C13 O2 -0.59(3) 3_666 . . . ?
C2 C1 C13 C12 -0.852(18) . . . . ?
C1 C1 C13 C12 179.843(19) 3_666 . . . ?
C11 C12 C13 O2 -0.01(3) . . . . ?
C3 C12 C13 O2 -179.347(16) . . . . ?
C11 C12 C13 C1 179.578(17) . . . . ?
C3 C12 C13 C1 0.240(18) . . . . ?

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.071

