# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Kyu1
_database_code_depnum_ccdc_archive 'CCDC 1993061'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Agou'
;Ibaraki University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 F3 O2'
_chemical_formula_sum            'C20 H21 F3 O2'
_chemical_formula_weight         350.37

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'
F F 0.0171 0.0103 '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                   10.8717(3)
_cell_length_b                   10.7087(3)
_cell_length_c                   15.1761(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.029(2)
_cell_angle_gamma                90
_cell_volume                     1760.03(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13448
_cell_measurement_theta_min      2.7120
_cell_measurement_theta_max      30.2250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax'
_diffrn_measurement_device_type  'Pilatus P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20387
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.675
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3265
_reflns_number_gt                3003
_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       'CrystalClear-SM Expert ver 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_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)+(0.0453P)²+0.7271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3265
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.10983(14) 0.54341(17) 0.42684(11) 0.0458(4) Uani 1 1 d . . . . .
H1 H 0.1500 0.4821 0.4678 0.069 Uiso 1 1 calc R U . . .
H2 H 0.0381 0.5049 0.3938 0.069 Uiso 1 1 calc R U . . .
H3 H 0.0828 0.6151 0.4603 0.069 Uiso 1 1 calc R U . . .
C2 C 0.19936(13) 0.58631(16) 0.36353(10) 0.0385(3) Uani 1 1 d . . . . .
H4 H 0.1585 0.6493 0.3232 0.046 Uiso 1 1 calc R U . . .
H5 H 0.2218 0.5144 0.3272 0.046 Uiso 1 1 calc R U . . .
C3 C 0.31697(11) 0.64274(12) 0.40922(8) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.3542 0.5809 0.4521 0.030 Uiso 1 1 calc R U . . .
H7 H 0.2938 0.7166 0.4433 0.030 Uiso 1 1 calc R U . . .
C4 C 0.41754(10) 0.68354(11) 0.34798(7) 0.0212(2) Uani 1 1 d . . . . .
C5 C 0.37550(12) 0.80035(12) 0.29506(8) 0.0276(3) Uani 1 1 d . . . . .
F1 F 0.46026(7) 0.83989(8) 0.24250(5) 0.0376(2) Uani 1 1 d . . . . .
F2 F 0.35459(8) 0.89594(7) 0.34879(6) 0.0424(2) Uani 1 1 d . . . . .
F3 F 0.27041(7) 0.78480(7) 0.24244(5) 0.0368(2) Uani 1 1 d . . . . .
C6 C 0.54025(11) 0.71680(11) 0.40119(7) 0.0208(2) Uani 1 1 d . . . . .
C7 C 0.65209(11) 0.70019(11) 0.36399(8) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.6517 0.6676 0.3058 0.028 Uiso 1 1 calc R U . . .
C8 C 0.76360(11) 0.73034(12) 0.41030(8) 0.0268(3) Uani 1 1 d . . . . .
H9 H 0.8389 0.7167 0.3844 0.032 Uiso 1 1 calc R U . . .
C9 C 0.76511(12) 0.78073(12) 0.49495(8) 0.0271(3) Uani 1 1 d . . . . .
C10 C 0.65474(12) 0.80074(12) 0.53219(8) 0.0281(3) Uani 1 1 d . . . . .
H10 H 0.6552 0.8366 0.5895 0.034 Uiso 1 1 calc R U . . .
C11 C 0.54350(11) 0.76830(12) 0.48571(8) 0.0253(3) Uani 1 1 d . . . . .
H11 H 0.4684 0.7815 0.5120 0.030 Uiso 1 1 calc R U . . .
O1 O 0.87770(9) 0.81005(11) 0.53639(6) 0.0398(3) Uani 1 1 d . . . . .
H12 H 0.8686 0.8395 0.5867 0.060 Uiso 1 1 calc R U . . .
C12 C 0.43775(10) 0.57396(11) 0.28447(7) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.41226(8) 0.58175(9) 0.20531(5) 0.0307(2) Uani 1 1 d . . . . .
C13 C 0.48916(11) 0.45432(11) 0.32558(8) 0.0235(3) Uani 1 1 d . . . . .
H13 H 0.4209 0.4053 0.3475 0.028 Uiso 1 1 calc R U . . .
H14 H 0.5482 0.4749 0.3769 0.028 Uiso 1 1 calc R U . . .
C14 C 0.55476(13) 0.37454(13) 0.26013(8) 0.0297(3) Uani 1 1 d . . . . .
H15 H 0.4923 0.3351 0.2175 0.036 Uiso 1 1 calc R U . . .
H16 H 0.6073 0.4290 0.2264 0.036 Uiso 1 1 calc R U . . .
C15 C 0.63366(11) 0.27421(12) 0.30633(8) 0.0253(3) Uani 1 1 d . . . . .
C16 C 0.59378(12) 0.15118(13) 0.31062(9) 0.0304(3) Uani 1 1 d . . . . .
H17 H 0.5156 0.1285 0.2823 0.036 Uiso 1 1 calc R U . . .
C17 C 0.66638(14) 0.06097(13) 0.35560(10) 0.0375(3) Uani 1 1 d . . . . .
H18 H 0.6374 -0.0225 0.3583 0.045 Uiso 1 1 calc R U . . .
C18 C 0.78070(14) 0.09256(14) 0.39650(9) 0.0378(3) Uani 1 1 d . . . . .
H19 H 0.8304 0.0311 0.4276 0.045 Uiso 1 1 calc R U . . .
C19 C 0.82230(13) 0.21418(14) 0.39192(9) 0.0371(3) Uani 1 1 d . . . . .
H20 H 0.9012 0.2361 0.4194 0.045 Uiso 1 1 calc R U . . .
C20 C 0.74928(12) 0.30427(13) 0.34746(9) 0.0324(3) Uani 1 1 d . . . . .
H21 H 0.7786 0.3877 0.3451 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.499(2) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
C2 C3 1.5249(17) . ?
C2 H4 0.9900 . ?
C2 H5 0.9900 . ?
C3 C4 1.5583(16) . ?
C3 H6 0.9900 . ?
C3 H7 0.9900 . ?
C4 C5 1.5343(16) . ?
C4 C6 1.5394(15) . ?
C4 C12 1.5464(16) . ?
C5 F1 1.3392(16) . ?
C5 F2 1.3405(15) . ?
C5 F3 1.3458(14) . ?
C6 C11 1.3937(16) . ?
C6 C7 1.3962(17) . ?
C7 C8 1.3851(17) . ?
C7 H8 0.9500 . ?
C8 C9 1.3921(18) . ?
C8 H9 0.9500 . ?
C9 O1 1.3628(15) . ?
C9 C10 1.3871(19) . ?
C10 C11 1.3897(18) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
O1 H12 0.8400 . ?
C12 O2 1.2120(14) . ?
C12 C13 1.5105(16) . ?
C13 C14 1.5328(17) . ?
C13 H13 0.9900 . ?
C13 H14 0.9900 . ?
C14 C15 1.5088(17) . ?
C14 H15 0.9900 . ?
C14 H16 0.9900 . ?
C15 C16 1.3903(19) . ?
C15 C20 1.3913(18) . ?
C16 C17 1.388(2) . ?
C16 H17 0.9500 . ?
C17 C18 1.382(2) . ?
C17 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C18 H19 0.9500 . ?
C19 C20 1.386(2) . ?
C19 H20 0.9500 . ?
C20 H21 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
C2 C1 H1 109.5 . . ?
C2 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
C2 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C1 C2 C3 113.32(12) . . ?
C1 C2 H4 108.9 . . ?
C3 C2 H4 108.9 . . ?
C1 C2 H5 108.9 . . ?
C3 C2 H5 108.9 . . ?
H4 C2 H5 107.7 . . ?
C2 C3 C4 116.37(10) . . ?
C2 C3 H6 108.2 . . ?
C4 C3 H6 108.2 . . ?
C2 C3 H7 108.2 . . ?
C4 C3 H7 108.2 . . ?
H6 C3 H7 107.3 . . ?
C5 C4 C6 106.90(9) . . ?
C5 C4 C12 110.16(9) . . ?
C6 C4 C12 109.79(9) . . ?
C5 C4 C3 110.39(10) . . ?
C6 C4 C3 111.90(9) . . ?
C12 C4 C3 107.72(9) . . ?
F1 C5 F2 106.44(10) . . ?
F1 C5 F3 106.16(10) . . ?
F2 C5 F3 105.97(10) . . ?
F1 C5 C4 112.37(10) . . ?
F2 C5 C4 111.27(10) . . ?
F3 C5 C4 114.09(10) . . ?
C11 C6 C7 118.02(11) . . ?
C11 C6 C4 121.69(10) . . ?
C7 C6 C4 120.25(10) . . ?
C8 C7 C6 121.31(11) . . ?
C8 C7 H8 119.3 . . ?
C6 C7 H8 119.3 . . ?
C7 C8 C9 119.84(11) . . ?
C7 C8 H9 120.1 . . ?
C9 C8 H9 120.1 . . ?
O1 C9 C10 123.39(11) . . ?
O1 C9 C8 116.91(11) . . ?
C10 C9 C8 119.69(11) . . ?
C9 C10 C11 119.99(11) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 121.12(11) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C9 O1 H12 109.5 . . ?
O2 C12 C13 120.79(11) . . ?
O2 C12 C4 122.20(11) . . ?
C13 C12 C4 117.00(9) . . ?
C12 C13 C14 112.42(10) . . ?
C12 C13 H13 109.1 . . ?
C14 C13 H13 109.1 . . ?
C12 C13 H14 109.1 . . ?
C14 C13 H14 109.1 . . ?
H13 C13 H14 107.9 . . ?
C15 C14 C13 111.94(10) . . ?
C15 C14 H15 109.2 . . ?
C13 C14 H15 109.2 . . ?
C15 C14 H16 109.2 . . ?
C13 C14 H16 109.2 . . ?
H15 C14 H16 107.9 . . ?
C16 C15 C20 118.13(12) . . ?
C16 C15 C14 121.98(12) . . ?
C20 C15 C14 119.88(12) . . ?
C17 C16 C15 121.08(12) . . ?
C17 C16 H17 119.5 . . ?
C15 C16 H17 119.5 . . ?
C18 C17 C16 120.04(13) . . ?
C18 C17 H18 120.0 . . ?
C16 C17 H18 120.0 . . ?
C17 C18 C19 119.57(13) . . ?
C17 C18 H19 120.2 . . ?
C19 C18 H19 120.2 . . ?
C18 C19 C20 120.27(13) . . ?
C18 C19 H20 119.9 . . ?
C20 C19 H20 119.9 . . ?
C19 C20 C15 120.90(13) . . ?
C19 C20 H21 119.5 . . ?
C15 C20 H21 119.5 . . ?

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
C1 C2 C3 C4 177.06(13) . . . . ?
C2 C3 C4 C5 71.32(14) . . . . ?
C2 C3 C4 C6 -169.76(11) . . . . ?
C2 C3 C4 C12 -49.00(14) . . . . ?
C6 C4 C5 F1 57.06(13) . . . . ?
C12 C4 C5 F1 -62.18(13) . . . . ?
C3 C4 C5 F1 178.98(10) . . . . ?
C6 C4 C5 F2 -62.20(13) . . . . ?
C12 C4 C5 F2 178.57(10) . . . . ?
C3 C4 C5 F2 59.73(13) . . . . ?
C6 C4 C5 F3 177.97(10) . . . . ?
C12 C4 C5 F3 58.74(13) . . . . ?
C3 C4 C5 F3 -60.10(13) . . . . ?
C5 C4 C6 C11 89.21(13) . . . . ?
C12 C4 C6 C11 -151.32(11) . . . . ?
C3 C4 C6 C11 -31.76(15) . . . . ?
C5 C4 C6 C7 -88.32(13) . . . . ?
C12 C4 C6 C7 31.15(14) . . . . ?
C3 C4 C6 C7 150.71(11) . . . . ?
C11 C6 C7 C8 1.87(18) . . . . ?
C4 C6 C7 C8 179.49(11) . . . . ?
C6 C7 C8 C9 -1.38(19) . . . . ?
C7 C8 C9 O1 -179.05(12) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
O1 C9 C10 C11 180.00(12) . . . . ?
C8 C9 C10 C11 1.2(2) . . . . ?
C9 C10 C11 C6 -0.7(2) . . . . ?
C7 C6 C11 C10 -0.83(18) . . . . ?
C4 C6 C11 C10 -178.41(11) . . . . ?
C5 C4 C12 O2 -5.75(15) . . . . ?
C6 C4 C12 O2 -123.21(12) . . . . ?
C3 C4 C12 O2 114.71(12) . . . . ?
C5 C4 C12 C13 175.29(10) . . . . ?
C6 C4 C12 C13 57.83(13) . . . . ?
C3 C4 C12 C13 -64.25(12) . . . . ?
O2 C12 C13 C14 24.88(16) . . . . ?
C4 C12 C13 C14 -156.15(10) . . . . ?
C12 C13 C14 C15 164.96(10) . . . . ?
C13 C14 C15 C16 99.89(14) . . . . ?
C13 C14 C15 C20 -79.07(15) . . . . ?
C20 C15 C16 C17 0.81(19) . . . . ?
C14 C15 C16 C17 -178.17(12) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C19 -0.3(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C18 C19 C20 C15 -0.4(2) . . . . ?
C16 C15 C20 C19 -0.38(19) . . . . ?
C14 C15 C20 C19 178.62(12) . . . . ?

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
O1 H12 O2 0.84 2.01 2.8083(13) 159.3 4_676

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.035



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Kyu3
_database_code_depnum_ccdc_archive 'CCDC 1993063'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Agou'
;Ibaraki University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 F3 O2'
_chemical_formula_sum            'C17 H17 F3 O2'
_chemical_formula_weight         310.30

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   24.3360(11)
_cell_length_b                   7.1684(3)
_cell_length_c                   16.7513(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2922.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8196
_cell_measurement_theta_min      2.5560
_cell_measurement_theta_max      28.9280

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.24460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.338
_oxdiff_exptl_absorpt_empirical_full_max 2.154
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax'
_diffrn_measurement_device_type  'Pilatus P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20991
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.432
_diffrn_reflns_theta_max         25.499
_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             2724
_reflns_number_gt                2283
_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       'CrystalClear-SM Expert ver 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_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)+(0.0422P)²+0.9146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2724
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.31384(4) 0.50028(13) 0.71333(5) 0.0388(3) Uani 1 1 d . . . . .
F2 F 0.28895(4) 0.30578(14) 0.62355(6) 0.0395(3) Uani 1 1 d . . . . .
F3 F 0.33099(4) 0.55807(13) 0.59066(6) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.48005(4) 0.12699(16) 0.34973(6) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.4567 0.0771 0.3195 0.049 Uiso 1 1 calc R U . . .
O2 O 0.43849(4) 0.08909(16) 0.72616(6) 0.0319(3) Uani 1 1 d . . . . .
H2 H 0.4546 0.0447 0.6861 0.048 Uiso 1 1 calc R U . . .
C1 C 0.40948(6) 0.27934(19) 0.56829(8) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.35419(6) 0.1704(2) 0.78468(8) 0.0230(3) Uani 1 1 d . . . . .
C3 C 0.45519(6) 0.1788(2) 0.41990(9) 0.0248(3) Uani 1 1 d . . . . .
C4 C 0.38674(6) 0.3258(2) 0.65199(8) 0.0231(3) Uani 1 1 d . . . . .
C5 C 0.38307(6) 0.1389(2) 0.70487(8) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.39885(6) 0.1835(2) 0.43003(9) 0.0284(4) Uani 1 1 d . . . . .
H3 H 0.3753 0.1538 0.3866 0.034 Uiso 1 1 calc R U . . .
C7 C 0.37669(6) 0.2314(2) 0.50348(9) 0.0279(3) Uani 1 1 d . . . . .
H4 H 0.3379 0.2314 0.5097 0.034 Uiso 1 1 calc R U . . .
C8 C 0.38198(6) 0.2533(2) 0.84825(9) 0.0277(3) Uani 1 1 d . . . . .
H5 H 0.4190 0.2922 0.8414 0.033 Uiso 1 1 calc R U . . .
C9 C 0.30026(6) 0.1139(2) 0.79722(10) 0.0300(4) Uani 1 1 d . . . . .
H6 H 0.2805 0.0568 0.7549 0.036 Uiso 1 1 calc R U . . .
C10 C 0.46609(6) 0.2788(2) 0.55547(9) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.4898 0.3140 0.5979 0.035 Uiso 1 1 calc R U . . .
C11 C 0.48872(6) 0.2285(2) 0.48288(9) 0.0309(4) Uani 1 1 d . . . . .
H8 H 0.5275 0.2281 0.4763 0.037 Uiso 1 1 calc R U . . .
C12 C 0.33038(7) 0.4194(2) 0.64496(9) 0.0303(4) Uani 1 1 d . . . . .
C13 C 0.35657(7) 0.2799(2) 0.92102(10) 0.0334(4) Uani 1 1 d . . . . .
H9 H 0.3761 0.3378 0.9634 0.040 Uiso 1 1 calc R U . . .
C14 C 0.30277(7) 0.2226(2) 0.93253(10) 0.0354(4) Uani 1 1 d . . . . .
H10 H 0.2853 0.2403 0.9827 0.043 Uiso 1 1 calc R U . . .
C15 C 0.42370(7) 0.4726(2) 0.69279(9) 0.0335(4) Uani 1 1 d . . . . .
H11 H 0.4291 0.5786 0.6567 0.050 Uiso 1 1 calc R U . . .
H12 H 0.4594 0.4167 0.7055 0.050 Uiso 1 1 calc R U . . .
H13 H 0.4061 0.5158 0.7420 0.050 Uiso 1 1 calc R U . . .
C16 C 0.35882(7) -0.0257(2) 0.65912(10) 0.0338(4) Uani 1 1 d . . . . .
H14 H 0.3825 -0.0557 0.6136 0.051 Uiso 1 1 calc R U . . .
H15 H 0.3220 0.0070 0.6399 0.051 Uiso 1 1 calc R U . . .
H16 H 0.3564 -0.1342 0.6945 0.051 Uiso 1 1 calc R U . . .
C17 C 0.27485(7) 0.1395(2) 0.87036(10) 0.0354(4) Uani 1 1 d . . . . .
H17 H 0.2380 0.0996 0.8778 0.042 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
F1 C12 1.3452(17) . ?
F2 C12 1.3450(19) . ?
F3 C12 1.3473(18) . ?
O1 C3 1.3732(17) . ?
O1 H1 0.8400 . ?
O2 C5 1.4401(17) . ?
O2 H2 0.8400 . ?
C1 C7 1.391(2) . ?
C1 C10 1.394(2) . ?
C1 C4 1.5437(19) . ?
C2 C9 1.389(2) . ?
C2 C8 1.395(2) . ?
C2 C5 1.5272(19) . ?
C3 C11 1.380(2) . ?
C3 C6 1.382(2) . ?
C4 C12 1.531(2) . ?
C4 C15 1.544(2) . ?
C4 C5 1.6088(19) . ?
C5 C16 1.526(2) . ?
C6 C7 1.387(2) . ?
C6 H3 0.9500 . ?
C7 H4 0.9500 . ?
C8 C13 1.380(2) . ?
C8 H5 0.9500 . ?
C9 C17 1.385(2) . ?
C9 H6 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H7 0.9500 . ?
C11 H8 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H9 0.9500 . ?
C14 C17 1.379(2) . ?
C14 H10 0.9500 . ?
C15 H11 0.9800 . ?
C15 H12 0.9800 . ?
C15 H13 0.9800 . ?
C16 H14 0.9800 . ?
C16 H15 0.9800 . ?
C16 H16 0.9800 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
C7 C1 C10 116.50(13) . . ?
C7 C1 C4 123.82(12) . . ?
C10 C1 C4 119.65(13) . . ?
C9 C2 C8 117.83(14) . . ?
C9 C2 C5 121.60(13) . . ?
C8 C2 C5 120.55(13) . . ?
O1 C3 C11 117.61(13) . . ?
O1 C3 C6 123.27(13) . . ?
C11 C3 C6 119.11(13) . . ?
C12 C4 C15 104.89(12) . . ?
C12 C4 C1 110.23(12) . . ?
C15 C4 C1 109.89(12) . . ?
C12 C4 C5 110.96(12) . . ?
C15 C4 C5 110.88(12) . . ?
C1 C4 C5 109.89(11) . . ?
O2 C5 C16 107.15(12) . . ?
O2 C5 C2 104.53(11) . . ?
C16 C5 C2 112.08(12) . . ?
O2 C5 C4 106.91(11) . . ?
C16 C5 C4 112.90(12) . . ?
C2 C5 C4 112.61(11) . . ?
C3 C6 C7 120.04(14) . . ?
C3 C6 H3 120.0 . . ?
C7 C6 H3 120.0 . . ?
C6 C7 C1 122.06(13) . . ?
C6 C7 H4 119.0 . . ?
C1 C7 H4 119.0 . . ?
C13 C8 C2 121.07(14) . . ?
C13 C8 H5 119.5 . . ?
C2 C8 H5 119.5 . . ?
C17 C9 C2 121.13(15) . . ?
C17 C9 H6 119.4 . . ?
C2 C9 H6 119.4 . . ?
C11 C10 C1 121.99(14) . . ?
C11 C10 H7 119.0 . . ?
C1 C10 H7 119.0 . . ?
C3 C11 C10 120.25(14) . . ?
C3 C11 H8 119.9 . . ?
C10 C11 H8 119.9 . . ?
F2 C12 F1 105.29(12) . . ?
F2 C12 F3 105.97(13) . . ?
F1 C12 F3 105.09(12) . . ?
F2 C12 C4 115.24(13) . . ?
F1 C12 C4 113.04(13) . . ?
F3 C12 C4 111.42(12) . . ?
C8 C13 C14 120.36(15) . . ?
C8 C13 H9 119.8 . . ?
C14 C13 H9 119.8 . . ?
C17 C14 C13 119.25(15) . . ?
C17 C14 H10 120.4 . . ?
C13 C14 H10 120.4 . . ?
C4 C15 H11 109.5 . . ?
C4 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
C4 C15 H13 109.5 . . ?
H11 C15 H13 109.5 . . ?
H12 C15 H13 109.5 . . ?
C5 C16 H14 109.5 . . ?
C5 C16 H15 109.5 . . ?
H14 C16 H15 109.5 . . ?
C5 C16 H16 109.5 . . ?
H14 C16 H16 109.5 . . ?
H15 C16 H16 109.5 . . ?
C14 C17 C9 120.37(15) . . ?
C14 C17 H17 119.8 . . ?
C9 C17 H17 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C4 C12 -32.40(19) . . . . ?
C10 C1 C4 C12 149.59(14) . . . . ?
C7 C1 C4 C15 -147.53(14) . . . . ?
C10 C1 C4 C15 34.46(18) . . . . ?
C7 C1 C4 C5 90.20(16) . . . . ?
C10 C1 C4 C5 -87.82(16) . . . . ?
C9 C2 C5 O2 -141.33(14) . . . . ?
C8 C2 C5 O2 37.08(17) . . . . ?
C9 C2 C5 C16 -25.61(19) . . . . ?
C8 C2 C5 C16 152.79(14) . . . . ?
C9 C2 C5 C4 102.99(16) . . . . ?
C8 C2 C5 C4 -78.61(16) . . . . ?
C12 C4 C5 O2 -164.85(11) . . . . ?
C15 C4 C5 O2 -48.71(15) . . . . ?
C1 C4 C5 O2 72.98(13) . . . . ?
C12 C4 C5 C16 77.57(15) . . . . ?
C15 C4 C5 C16 -166.29(13) . . . . ?
C1 C4 C5 C16 -44.60(16) . . . . ?
C12 C4 C5 C2 -50.61(16) . . . . ?
C15 C4 C5 C2 65.54(15) . . . . ?
C1 C4 C5 C2 -172.78(11) . . . . ?
O1 C3 C6 C7 177.87(14) . . . . ?
C11 C3 C6 C7 -2.2(2) . . . . ?
C3 C6 C7 C1 1.3(2) . . . . ?
C10 C1 C7 C6 0.6(2) . . . . ?
C4 C1 C7 C6 -177.42(14) . . . . ?
C9 C2 C8 C13 -0.5(2) . . . . ?
C5 C2 C8 C13 -179.00(14) . . . . ?
C8 C2 C9 C17 0.1(2) . . . . ?
C5 C2 C9 C17 178.57(14) . . . . ?
C7 C1 C10 C11 -1.7(2) . . . . ?
C4 C1 C10 C11 176.49(14) . . . . ?
O1 C3 C11 C10 -178.86(14) . . . . ?
C6 C3 C11 C10 1.2(2) . . . . ?
C1 C10 C11 C3 0.8(2) . . . . ?
C15 C4 C12 F2 -169.00(12) . . . . ?
C1 C4 C12 F2 72.76(15) . . . . ?
C5 C4 C12 F2 -49.21(16) . . . . ?
C15 C4 C12 F1 -47.85(16) . . . . ?
C1 C4 C12 F1 -166.10(12) . . . . ?
C5 C4 C12 F1 71.93(16) . . . . ?
C15 C4 C12 F3 70.23(15) . . . . ?
C1 C4 C12 F3 -48.02(17) . . . . ?
C5 C4 C12 F3 -169.99(12) . . . . ?
C2 C8 C13 C14 0.6(2) . . . . ?
C8 C13 C14 C17 -0.3(2) . . . . ?
C13 C14 C17 C9 -0.1(2) . . . . ?
C2 C9 C17 C14 0.2(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
O1 H1 O2 0.84 2.02 2.7761(15) 150.2 8
O2 H2 O1 0.84 2.10 2.8186(14) 143.6 5_656
C16 H15 F2 0.98 2.30 2.9821(19) 125.5 .

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_Kyu4
_database_code_depnum_ccdc_archive 'CCDC 1993066'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Agou'
;Ibaraki University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Cl F3 O2, C4 H8 O2'
_chemical_formula_sum            'C26 H26 Cl F3 O4'
_chemical_formula_weight         494.92

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'
Cl Cl 0.1484 0.1585 '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                   12.0518(6)
_cell_length_b                   11.0358(4)
_cell_length_c                   18.5393(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.931(5)
_cell_angle_gamma                90
_cell_volume                     2393.22(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12255
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      30.248

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.817
_oxdiff_exptl_absorpt_empirical_full_max 1.327
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax'
_diffrn_measurement_device_type  'Pilatus P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28431
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4433
_reflns_number_gt                3822
_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       'CrystalClear-SM Expert ver 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_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)+(0.0729P)²+1.5111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4433
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Cl1 Cl 0.44827(5) 1.31090(5) 0.21559(4) 0.04704(19) Uani 1 1 d . . . . .
C1 C 0.46489(17) 1.16237(18) 0.18752(12) 0.0307(4) Uani 1 1 d . . . . .
C2 C 0.43375(18) 1.13416(18) 0.11302(12) 0.0318(4) Uani 1 1 d . . . . .
H1 H 0.4032 1.1948 0.0774 0.038 Uiso 1 1 calc R U . . .
C3 C 0.44744(16) 1.01592(18) 0.09050(10) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.4264 0.9971 0.0390 0.032 Uiso 1 1 calc R U . . .
C4 C 0.49104(15) 0.92423(16) 0.14102(10) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.52395(16) 0.95718(18) 0.21634(10) 0.0281(4) Uani 1 1 d . . . . .
H3 H 0.5555 0.8974 0.2523 0.034 Uiso 1 1 calc R U . . .
C6 C 0.51155(17) 1.07492(19) 0.23946(11) 0.0317(4) Uani 1 1 d . . . . .
H4 H 0.5350 1.0954 0.2907 0.038 Uiso 1 1 calc R U . . .
C7 C 0.49803(15) 0.79307(17) 0.11211(9) 0.0216(4) Uani 1 1 d . . . . .
O1 O 0.48111(11) 0.79605(12) 0.03341(6) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.4123 0.8119 0.0137 0.038 Uiso 1 1 calc R U . . .
C8 C 0.40262(15) 0.71514(17) 0.13141(10) 0.0246(4) Uani 1 1 d . . . . .
C9 C 0.36799(17) 0.7270(2) 0.19781(11) 0.0317(4) Uani 1 1 d . . . . .
H6 H 0.4058 0.7840 0.2339 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2803(2) 0.6581(2) 0.21233(14) 0.0428(6) Uani 1 1 d . . . . .
H7 H 0.2591 0.6674 0.2582 0.051 Uiso 1 1 calc R U . . .
C11 C 0.2233(2) 0.5757(2) 0.16054(17) 0.0539(7) Uani 1 1 d . . . . .
H8 H 0.1626 0.5285 0.1703 0.065 Uiso 1 1 calc R U . . .
C12 C 0.2553(2) 0.5628(2) 0.09415(16) 0.0505(6) Uani 1 1 d . . . . .
H9 H 0.2164 0.5063 0.0582 0.061 Uiso 1 1 calc R U . . .
C13 C 0.34377(18) 0.63143(19) 0.07962(12) 0.0342(5) Uani 1 1 d . . . . .
H10 H 0.3647 0.6214 0.0337 0.041 Uiso 1 1 calc R U . . .
C14 C 0.62596(15) 0.74083(17) 0.13941(10) 0.0233(4) Uani 1 1 d . . . . .
C15 C 0.70708(17) 0.83429(19) 0.11695(11) 0.0302(4) Uani 1 1 d . . . . .
H11 H 0.7044 0.9103 0.1439 0.045 Uiso 1 1 calc R U . . .
H12 H 0.6829 0.8493 0.0634 0.045 Uiso 1 1 calc R U . . .
H13 H 0.7853 0.8026 0.1294 0.045 Uiso 1 1 calc R U . . .
C16 C 0.64329(17) 0.62330(18) 0.09768(11) 0.0293(4) Uani 1 1 d . . . . .
F1 F 0.74727(10) 0.57538(12) 0.12851(7) 0.0400(3) Uani 1 1 d . . . . .
F2 F 0.56815(10) 0.53497(11) 0.09937(7) 0.0377(3) Uani 1 1 d . . . . .
F3 F 0.64297(12) 0.63940(12) 0.02605(7) 0.0453(3) Uani 1 1 d . . . . .
C17 C 0.66055(15) 0.71222(16) 0.22304(10) 0.0215(4) Uani 1 1 d . . . . .
C18 C 0.74596(15) 0.77829(17) 0.27122(10) 0.0253(4) Uani 1 1 d . . . . .
H14 H 0.7838 0.8413 0.2517 0.030 Uiso 1 1 calc R U . . .
C19 C 0.77718(16) 0.75441(18) 0.34695(10) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.8355 0.8009 0.3786 0.033 Uiso 1 1 calc R U . . .
C20 C 0.72313(16) 0.66283(18) 0.37606(10) 0.0255(4) Uani 1 1 d . . . . .
C21 C 0.63865(15) 0.59423(17) 0.32946(10) 0.0249(4) Uani 1 1 d . . . . .
H16 H 0.6015 0.5310 0.3493 0.030 Uiso 1 1 calc R U . . .
C22 C 0.60879(15) 0.61854(16) 0.25385(10) 0.0230(4) Uani 1 1 d . . . . .
H17 H 0.5518 0.5704 0.2223 0.028 Uiso 1 1 calc R U . . .
O2 O 0.75574(12) 0.64231(15) 0.45130(7) 0.0359(4) Uani 1 1 d . . . . .
H18 H 0.7135 0.5889 0.4629 0.054 Uiso 1 1 calc R U . . .
C27 C 0.6564(3) 0.5553(3) 0.61735(14) 0.0553(7) Uani 1 1 d . . . . .
H19 H 0.6832 0.6263 0.5946 0.083 Uiso 1 1 calc R U . . .
H20 H 0.7160 0.5293 0.6605 0.083 Uiso 1 1 calc R U . . .
H21 H 0.5871 0.5764 0.6333 0.083 Uiso 1 1 calc R U . . .
O5 O 0.63684(15) 0.46229(16) 0.49820(8) 0.0463(4) Uani 1 1 d . . . . .
C24 C 0.63076(19) 0.4553(2) 0.56227(12) 0.0386(5) Uani 1 1 d . . . . .
O4 O 0.5972(2) 0.35512(17) 0.59009(10) 0.0617(5) Uani 1 1 d . . . . .
C25 C 0.5683(5) 0.2502(3) 0.5398(2) 0.1023(16) Uani 1 1 d . . . . .
H26 H 0.5207 0.2770 0.4911 0.123 Uiso 1 1 calc R U . . .
H27 H 0.6391 0.2133 0.5315 0.123 Uiso 1 1 calc R U . . .
C26 C 0.5075(3) 0.1634(3) 0.5718(2) 0.0822(11) Uani 1 1 d . . . . .
H23 H 0.5549 0.1372 0.6199 0.123 Uiso 1 1 calc R U . . .
H24 H 0.4888 0.0934 0.5387 0.123 Uiso 1 1 calc R U . . .
H25 H 0.4368 0.1999 0.5790 0.123 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
Cl1 C1 1.746(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.392(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.405(3) . ?
C4 C7 1.553(3) . ?
C5 C6 1.388(3) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 O1 1.424(2) . ?
C7 C8 1.545(3) . ?
C7 C14 1.609(2) . ?
O1 H5 0.8400 . ?
C8 C13 1.397(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.381(3) . ?
C9 H6 0.9500 . ?
C10 C11 1.379(4) . ?
C10 H7 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H8 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H9 0.9500 . ?
C13 H10 0.9500 . ?
C14 C17 1.538(2) . ?
C14 C15 1.546(3) . ?
C14 C16 1.550(3) . ?
C15 H11 0.9800 . ?
C15 H12 0.9800 . ?
C15 H13 0.9800 . ?
C16 F2 1.336(2) . ?
C16 F3 1.339(2) . ?
C16 F1 1.353(2) . ?
C17 C18 1.395(3) . ?
C17 C22 1.399(3) . ?
C18 C19 1.388(3) . ?
C18 H14 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H15 0.9500 . ?
C20 O2 1.374(2) . ?
C20 C21 1.390(3) . ?
C21 C22 1.387(3) . ?
C21 H16 0.9500 . ?
C22 H17 0.9500 . ?
O2 H18 0.8400 . ?
C27 C24 1.484(3) . ?
C27 H19 0.9800 . ?
C27 H20 0.9800 . ?
C27 H21 0.9800 . ?
O5 C24 1.210(3) . ?
C24 O4 1.324(3) . ?
O4 C25 1.475(4) . ?
C25 C26 1.420(5) . ?
C25 H26 0.9900 . ?
C25 H27 0.9900 . ?
C26 H23 0.9800 . ?
C26 H24 0.9800 . ?
C26 H25 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 C1 C6 120.50(18) . . ?
C2 C1 Cl1 119.22(16) . . ?
C6 C1 Cl1 120.26(16) . . ?
C1 C2 C3 119.30(18) . . ?
C1 C2 H1 120.3 . . ?
C3 C2 H1 120.3 . . ?
C2 C3 C4 122.16(17) . . ?
C2 C3 H2 118.9 . . ?
C4 C3 H2 118.9 . . ?
C3 C4 C5 116.80(17) . . ?
C3 C4 C7 119.22(16) . . ?
C5 C4 C7 123.96(16) . . ?
C6 C5 C4 121.59(18) . . ?
C6 C5 H3 119.2 . . ?
C4 C5 H3 119.2 . . ?
C1 C6 C5 119.61(18) . . ?
C1 C6 H4 120.2 . . ?
C5 C6 H4 120.2 . . ?
O1 C7 C8 108.61(14) . . ?
O1 C7 C4 109.01(14) . . ?
C8 C7 C4 109.49(14) . . ?
O1 C7 C14 102.73(13) . . ?
C8 C7 C14 115.96(14) . . ?
C4 C7 C14 110.67(14) . . ?
C7 O1 H5 109.5 . . ?
C13 C8 C9 117.23(18) . . ?
C13 C8 C7 119.47(16) . . ?
C9 C8 C7 123.24(17) . . ?
C10 C9 C8 121.7(2) . . ?
C10 C9 H6 119.2 . . ?
C8 C9 H6 119.2 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H7 119.9 . . ?
C9 C10 H7 119.9 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H8 120.4 . . ?
C12 C11 H8 120.4 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H9 119.7 . . ?
C13 C12 H9 119.7 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 H10 119.5 . . ?
C8 C13 H10 119.5 . . ?
C17 C14 C15 111.90(15) . . ?
C17 C14 C16 107.15(15) . . ?
C15 C14 C16 104.72(15) . . ?
C17 C14 C7 113.40(14) . . ?
C15 C14 C7 107.24(14) . . ?
C16 C14 C7 112.14(15) . . ?
C14 C15 H11 109.5 . . ?
C14 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
C14 C15 H13 109.5 . . ?
H11 C15 H13 109.5 . . ?
H12 C15 H13 109.5 . . ?
F2 C16 F3 106.25(16) . . ?
F2 C16 F1 105.60(16) . . ?
F3 C16 F1 104.59(15) . . ?
F2 C16 C14 115.18(16) . . ?
F3 C16 C14 114.55(16) . . ?
F1 C16 C14 109.79(16) . . ?
C18 C17 C22 117.24(16) . . ?
C18 C17 C14 121.14(16) . . ?
C22 C17 C14 121.61(16) . . ?
C19 C18 C17 121.79(17) . . ?
C19 C18 H14 119.1 . . ?
C17 C18 H14 119.1 . . ?
C20 C19 C18 119.72(17) . . ?
C20 C19 H15 120.1 . . ?
C18 C19 H15 120.1 . . ?
O2 C20 C19 118.10(17) . . ?
O2 C20 C21 121.94(18) . . ?
C19 C20 C21 119.96(16) . . ?
C22 C21 C20 119.73(17) . . ?
C22 C21 H16 120.1 . . ?
C20 C21 H16 120.1 . . ?
C21 C22 C17 121.54(17) . . ?
C21 C22 H17 119.2 . . ?
C17 C22 H17 119.2 . . ?
C20 O2 H18 109.5 . . ?
C24 C27 H19 109.5 . . ?
C24 C27 H20 109.5 . . ?
H19 C27 H20 109.5 . . ?
C24 C27 H21 109.5 . . ?
H19 C27 H21 109.5 . . ?
H20 C27 H21 109.5 . . ?
O5 C24 O4 122.1(2) . . ?
O5 C24 C27 125.2(2) . . ?
O4 C24 C27 112.7(2) . . ?
C24 O4 C25 117.2(2) . . ?
C26 C25 O4 109.4(3) . . ?
C26 C25 H26 109.8 . . ?
O4 C25 H26 109.8 . . ?
C26 C25 H27 109.8 . . ?
O4 C25 H27 109.8 . . ?
H26 C25 H27 108.2 . . ?
C25 C26 H23 109.5 . . ?
C25 C26 H24 109.5 . . ?
H23 C26 H24 109.5 . . ?
C25 C26 H25 109.5 . . ?
H23 C26 H25 109.5 . . ?
H24 C26 H25 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
C6 C1 C2 C3 1.3(3) . . . . ?
Cl1 C1 C2 C3 179.70(15) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 C7 176.88(17) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C7 C4 C5 C6 -177.32(17) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
Cl1 C1 C6 C5 179.82(15) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C3 C4 C7 O1 13.5(2) . . . . ?
C5 C4 C7 O1 -168.02(16) . . . . ?
C3 C4 C7 C8 -105.21(18) . . . . ?
C5 C4 C7 C8 73.3(2) . . . . ?
C3 C4 C7 C14 125.76(17) . . . . ?
C5 C4 C7 C14 -55.7(2) . . . . ?
O1 C7 C8 C13 21.1(2) . . . . ?
C4 C7 C8 C13 140.03(18) . . . . ?
C14 C7 C8 C13 -93.9(2) . . . . ?
O1 C7 C8 C9 -156.28(17) . . . . ?
C4 C7 C8 C9 -37.3(2) . . . . ?
C14 C7 C8 C9 88.7(2) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C10 178.22(19) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C7 C8 C13 C12 -178.0(2) . . . . ?
O1 C7 C14 C17 -172.27(14) . . . . ?
C8 C7 C14 C17 -54.0(2) . . . . ?
C4 C7 C14 C17 71.49(18) . . . . ?
O1 C7 C14 C15 63.69(17) . . . . ?
C8 C7 C14 C15 -178.02(15) . . . . ?
C4 C7 C14 C15 -52.55(18) . . . . ?
O1 C7 C14 C16 -50.73(18) . . . . ?
C8 C7 C14 C16 67.55(19) . . . . ?
C4 C7 C14 C16 -166.98(14) . . . . ?
C17 C14 C16 F2 71.24(19) . . . . ?
C15 C14 C16 F2 -169.77(15) . . . . ?
C7 C14 C16 F2 -53.8(2) . . . . ?
C17 C14 C16 F3 -165.07(15) . . . . ?
C15 C14 C16 F3 -46.1(2) . . . . ?
C7 C14 C16 F3 69.9(2) . . . . ?
C17 C14 C16 F1 -47.8(2) . . . . ?
C15 C14 C16 F1 71.23(18) . . . . ?
C7 C14 C16 F1 -172.81(14) . . . . ?
C15 C14 C17 C18 8.1(2) . . . . ?
C16 C14 C17 C18 122.31(18) . . . . ?
C7 C14 C17 C18 -113.41(19) . . . . ?
C15 C14 C17 C22 -171.31(17) . . . . ?
C16 C14 C17 C22 -57.1(2) . . . . ?
C7 C14 C17 C22 67.2(2) . . . . ?
C22 C17 C18 C19 -1.4(3) . . . . ?
C14 C17 C18 C19 179.25(17) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 O2 -179.60(17) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
O2 C20 C21 C22 -179.99(17) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C17 -1.0(3) . . . . ?
C18 C17 C22 C21 1.8(3) . . . . ?
C14 C17 C22 C21 -178.84(16) . . . . ?
O5 C24 O4 C25 0.7(4) . . . . ?
C27 C24 O4 C25 179.4(3) . . . . ?
C24 O4 C25 C26 -165.2(3) . . . . ?

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
C2 H1 F3 0.95 2.61 3.550(2) 169.3 3_675
O1 H5 O2 0.84 2.03 2.8578(19) 170.6 4_575

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_Kyu2
_database_code_depnum_ccdc_archive 'CCDC 1993062'
loop_
_audit_author_name
_audit_author_address
' Tomohiro Agou'
;Ibaraki University
Japan
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 F3 O4 S'
_chemical_formula_sum            'C23 H21 F3 O4 S'
_chemical_formula_weight         450.46

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   13.8943(4)
_cell_length_b                   9.9889(3)
_cell_length_c                   15.0537(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.237(3)
_cell_angle_gamma                90
_cell_volume                     2062.19(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14703
_cell_measurement_theta_min      2.5940
_cell_measurement_theta_max      30.2440

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.843
_oxdiff_exptl_absorpt_empirical_full_max 1.284
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku VariMax'
_diffrn_measurement_device_type  'Pilatus P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24059
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.457
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3833
_reflns_number_gt                3453
_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       'CrystalClear-SM Expert ver 2.1'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_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)+(0.0492P)²+0.7299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
S1 S 0.83466(3) 0.56225(4) 0.38973(2) 0.03235(12) Uani 1 1 d . . . . .
F1 F 0.51749(8) 0.70526(10) 0.72897(8) 0.0551(3) Uani 1 1 d . . . . .
F2 F 0.50332(8) 0.58248(10) 0.84247(7) 0.0541(3) Uani 1 1 d . . . . .
O1 O 0.86014(7) 0.60851(10) 0.49271(7) 0.0329(2) Uani 1 1 d . . . . .
F3 F 0.64099(9) 0.67441(11) 0.83216(8) 0.0603(3) Uani 1 1 d . . . . .
O2 O 0.74256(8) 0.61773(12) 0.35101(7) 0.0407(3) Uani 1 1 d . . . . .
O3 O 0.92071(8) 0.59770(13) 0.35494(8) 0.0451(3) Uani 1 1 d . . . . .
O4 O 0.45958(8) 0.49746(11) 0.61363(9) 0.0477(3) Uani 1 1 d . . . . .
H1 H 0.4048 0.4663 0.5915 0.072 Uiso 1 1 calc R U . . .
C1 C 0.66701(10) 0.52604(13) 0.67379(9) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.79262(10) 0.58099(14) 0.55204(9) 0.0278(3) Uani 1 1 d . . . . .
C3 C 0.52440(10) 0.27674(14) 0.65515(9) 0.0284(3) Uani 1 1 d . . . . .
C4 C 0.75727(10) 0.46255(14) 0.67990(10) 0.0309(3) Uani 1 1 d . . . . .
H2 H 0.7762 0.3998 0.7269 0.037 Uiso 1 1 calc R U . . .
C5 C 0.82305(10) 0.38783(15) 0.39553(9) 0.0299(3) Uani 1 1 d . . . . .
C6 C 0.59541(10) 0.48706(14) 0.73771(10) 0.0300(3) Uani 1 1 d . . . . .
C7 C 0.82020(10) 0.48887(15) 0.61888(10) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.8811 0.4440 0.6234 0.038 Uiso 1 1 calc R U . . .
C8 C 0.70529(10) 0.64985(14) 0.54487(10) 0.0305(3) Uani 1 1 d . . . . .
H4 H 0.6885 0.7155 0.4994 0.037 Uiso 1 1 calc R U . . .
C9 C 0.64270(10) 0.62098(14) 0.60557(10) 0.0301(3) Uani 1 1 d . . . . .
H5 H 0.5821 0.6667 0.6007 0.036 Uiso 1 1 calc R U . . .
C10 C 0.57307(11) 0.25746(15) 0.58230(10) 0.0348(3) Uani 1 1 d . . . . .
H6 H 0.5900 0.3322 0.5489 0.042 Uiso 1 1 calc R U . . .
C11 C 0.50224(10) 0.41579(15) 0.68646(11) 0.0330(3) Uani 1 1 d . . . . .
H7 H 0.4543 0.4069 0.7290 0.040 Uiso 1 1 calc R U . . .
C12 C 0.80397(12) 0.11100(16) 0.40209(10) 0.0379(3) Uani 1 1 d . . . . .
C13 C 0.64240(11) 0.39391(16) 0.81438(10) 0.0371(3) Uani 1 1 d . . . . .
H8 H 0.6985 0.4390 0.8498 0.056 Uiso 1 1 calc R U . . .
H9 H 0.6642 0.3112 0.7887 0.056 Uiso 1 1 calc R U . . .
H10 H 0.5944 0.3723 0.8533 0.056 Uiso 1 1 calc R U . . .
C14 C 0.73677(11) 0.32825(17) 0.35602(10) 0.0365(3) Uani 1 1 d . . . . .
H11 H 0.6841 0.3812 0.3271 0.044 Uiso 1 1 calc R U . . .
C15 C 0.90062(11) 0.31118(17) 0.43758(11) 0.0377(3) Uani 1 1 d . . . . .
H12 H 0.9600 0.3526 0.4637 0.045 Uiso 1 1 calc R U . . .
C16 C 0.49705(12) 0.16531(16) 0.70040(11) 0.0378(3) Uani 1 1 d . . . . .
H13 H 0.4620 0.1770 0.7491 0.045 Uiso 1 1 calc R U . . .
C17 C 0.56405(12) 0.61323(16) 0.78391(11) 0.0408(4) Uani 1 1 d . . . . .
C18 C 0.72842(12) 0.19019(17) 0.35932(11) 0.0409(4) Uani 1 1 d . . . . .
H14 H 0.6696 0.1488 0.3317 0.049 Uiso 1 1 calc R U . . .
C19 C 0.57100(13) 0.01958(17) 0.60503(13) 0.0473(4) Uani 1 1 d . . . . .
H15 H 0.5882 -0.0680 0.5885 0.057 Uiso 1 1 calc R U . . .
C20 C 0.52037(13) 0.03708(16) 0.67535(12) 0.0442(4) Uani 1 1 d . . . . .
H16 H 0.5013 -0.0384 0.7068 0.053 Uiso 1 1 calc R U . . .
C21 C 0.89016(12) 0.17416(17) 0.44090(11) 0.0410(4) Uani 1 1 d . . . . .
H17 H 0.9428 0.1215 0.4702 0.049 Uiso 1 1 calc R U . . .
C22 C 0.59681(13) 0.12881(18) 0.55845(12) 0.0463(4) Uani 1 1 d . . . . .
H18 H 0.6312 0.1161 0.5094 0.056 Uiso 1 1 calc R U . . .
C23 C 0.79181(15) -0.03824(18) 0.40672(15) 0.0551(5) Uani 1 1 d . . . . .
H19 H 0.7292 -0.0588 0.4258 0.083 Uiso 1 1 calc R U . . .
H20 H 0.8450 -0.0759 0.4502 0.083 Uiso 1 1 calc R U . . .
H21 H 0.7933 -0.0773 0.3472 0.083 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
S1 O3 1.4249(11) . ?
S1 O2 1.4300(11) . ?
S1 O1 1.6019(11) . ?
S1 C5 1.7531(16) . ?
F1 C17 1.333(2) . ?
F2 C17 1.3499(18) . ?
O1 C2 1.4221(16) . ?
F3 C17 1.340(2) . ?
O4 C11 1.4179(19) . ?
O4 H1 0.8400 . ?
C1 C4 1.395(2) . ?
C1 C9 1.399(2) . ?
C1 C6 1.5410(19) . ?
C2 C7 1.372(2) . ?
C2 C8 1.384(2) . ?
C3 C16 1.389(2) . ?
C3 C10 1.391(2) . ?
C3 C11 1.5142(19) . ?
C4 C7 1.391(2) . ?
C4 H2 0.9500 . ?
C5 C14 1.384(2) . ?
C5 C15 1.389(2) . ?
C6 C17 1.536(2) . ?
C6 C13 1.543(2) . ?
C6 C11 1.5675(19) . ?
C7 H3 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H4 0.9500 . ?
C9 H5 0.9500 . ?
C10 C22 1.388(2) . ?
C10 H6 0.9500 . ?
C11 H7 1.0000 . ?
C12 C18 1.388(2) . ?
C12 C21 1.396(2) . ?
C12 C23 1.503(2) . ?
C13 H8 0.9800 . ?
C13 H9 0.9800 . ?
C13 H10 0.9800 . ?
C14 C18 1.386(2) . ?
C14 H11 0.9500 . ?
C15 C21 1.378(2) . ?
C15 H12 0.9500 . ?
C16 C20 1.388(2) . ?
C16 H13 0.9500 . ?
C18 H14 0.9500 . ?
C19 C20 1.373(3) . ?
C19 C22 1.375(3) . ?
C19 H15 0.9500 . ?
C20 H16 0.9500 . ?
C21 H17 0.9500 . ?
C22 H18 0.9500 . ?
C23 H19 0.9800 . ?
C23 H20 0.9800 . ?
C23 H21 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
O3 S1 O2 120.18(7) . . ?
O3 S1 O1 102.46(6) . . ?
O2 S1 O1 109.09(6) . . ?
O3 S1 C5 110.77(7) . . ?
O2 S1 C5 108.79(7) . . ?
O1 S1 C5 104.26(6) . . ?
C2 O1 S1 119.10(8) . . ?
C11 O4 H1 109.5 . . ?
C4 C1 C9 117.73(13) . . ?
C4 C1 C6 120.50(12) . . ?
C9 C1 C6 121.71(12) . . ?
C7 C2 C8 121.92(13) . . ?
C7 C2 O1 117.09(12) . . ?
C8 C2 O1 120.90(12) . . ?
C16 C3 C10 118.78(14) . . ?
C16 C3 C11 119.80(13) . . ?
C10 C3 C11 121.41(13) . . ?
C7 C4 C1 121.61(13) . . ?
C7 C4 H2 119.2 . . ?
C1 C4 H2 119.2 . . ?
C14 C5 C15 120.92(15) . . ?
C14 C5 S1 119.09(11) . . ?
C15 C5 S1 119.97(11) . . ?
C17 C6 C1 109.51(11) . . ?
C17 C6 C13 105.82(12) . . ?
C1 C6 C13 112.41(12) . . ?
C17 C6 C11 108.88(12) . . ?
C1 C6 C11 111.87(11) . . ?
C13 C6 C11 108.12(12) . . ?
C2 C7 C4 118.68(13) . . ?
C2 C7 H3 120.7 . . ?
C4 C7 H3 120.7 . . ?
C2 C8 C9 118.64(13) . . ?
C2 C8 H4 120.7 . . ?
C9 C8 H4 120.7 . . ?
C8 C9 C1 121.38(13) . . ?
C8 C9 H5 119.3 . . ?
C1 C9 H5 119.3 . . ?
C22 C10 C3 119.86(14) . . ?
C22 C10 H6 120.1 . . ?
C3 C10 H6 120.1 . . ?
O4 C11 C3 111.58(13) . . ?
O4 C11 C6 109.21(12) . . ?
C3 C11 C6 112.13(11) . . ?
O4 C11 H7 107.9 . . ?
C3 C11 H7 107.9 . . ?
C6 C11 H7 107.9 . . ?
C18 C12 C21 118.09(15) . . ?
C18 C12 C23 120.30(16) . . ?
C21 C12 C23 121.60(16) . . ?
C6 C13 H8 109.5 . . ?
C6 C13 H9 109.5 . . ?
H8 C13 H9 109.5 . . ?
C6 C13 H10 109.5 . . ?
H8 C13 H10 109.5 . . ?
H9 C13 H10 109.5 . . ?
C5 C14 C18 118.97(14) . . ?
C5 C14 H11 120.5 . . ?
C18 C14 H11 120.5 . . ?
C21 C15 C5 119.03(14) . . ?
C21 C15 H12 120.5 . . ?
C5 C15 H12 120.5 . . ?
C20 C16 C3 120.78(15) . . ?
C20 C16 H13 119.6 . . ?
C3 C16 H13 119.6 . . ?
F1 C17 F3 106.70(13) . . ?
F1 C17 F2 105.67(13) . . ?
F3 C17 F2 106.13(13) . . ?
F1 C17 C6 115.44(13) . . ?
F3 C17 C6 111.11(13) . . ?
F2 C17 C6 111.20(12) . . ?
C14 C18 C12 121.50(15) . . ?
C14 C18 H14 119.2 . . ?
C12 C18 H14 119.2 . . ?
C20 C19 C22 119.99(15) . . ?
C20 C19 H15 120.0 . . ?
C22 C19 H15 120.0 . . ?
C19 C20 C16 119.85(16) . . ?
C19 C20 H16 120.1 . . ?
C16 C20 H16 120.1 . . ?
C15 C21 C12 121.47(15) . . ?
C15 C21 H17 119.3 . . ?
C12 C21 H17 119.3 . . ?
C19 C22 C10 120.68(16) . . ?
C19 C22 H18 119.7 . . ?
C10 C22 H18 119.7 . . ?
C12 C23 H19 109.5 . . ?
C12 C23 H20 109.5 . . ?
H19 C23 H20 109.5 . . ?
C12 C23 H21 109.5 . . ?
H19 C23 H21 109.5 . . ?
H20 C23 H21 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
O3 S1 O1 C2 -175.92(10) . . . . ?
O2 S1 O1 C2 55.68(12) . . . . ?
C5 S1 O1 C2 -60.39(11) . . . . ?
S1 O1 C2 C7 111.66(12) . . . . ?
S1 O1 C2 C8 -71.59(15) . . . . ?
C9 C1 C4 C7 -2.0(2) . . . . ?
C6 C1 C4 C7 175.24(13) . . . . ?
O3 S1 C5 C14 -127.41(12) . . . . ?
O2 S1 C5 C14 6.76(13) . . . . ?
O1 S1 C5 C14 123.05(11) . . . . ?
O3 S1 C5 C15 51.13(14) . . . . ?
O2 S1 C5 C15 -174.69(11) . . . . ?
O1 S1 C5 C15 -58.41(13) . . . . ?
C4 C1 C6 C17 127.19(14) . . . . ?
C9 C1 C6 C17 -55.69(17) . . . . ?
C4 C1 C6 C13 9.87(18) . . . . ?
C9 C1 C6 C13 -173.01(12) . . . . ?
C4 C1 C6 C11 -112.00(14) . . . . ?
C9 C1 C6 C11 65.12(16) . . . . ?
C8 C2 C7 C4 1.3(2) . . . . ?
O1 C2 C7 C4 178.00(12) . . . . ?
C1 C4 C7 C2 0.9(2) . . . . ?
C7 C2 C8 C9 -2.2(2) . . . . ?
O1 C2 C8 C9 -178.78(12) . . . . ?
C2 C8 C9 C1 1.0(2) . . . . ?
C4 C1 C9 C8 1.1(2) . . . . ?
C6 C1 C9 C8 -176.14(12) . . . . ?
C16 C3 C10 C22 -2.6(2) . . . . ?
C11 C3 C10 C22 176.54(14) . . . . ?
C16 C3 C11 O4 -132.39(14) . . . . ?
C10 C3 C11 O4 48.50(18) . . . . ?
C16 C3 C11 C6 104.75(15) . . . . ?
C10 C3 C11 C6 -74.37(17) . . . . ?
C17 C6 C11 O4 67.49(15) . . . . ?
C1 C6 C11 O4 -53.68(15) . . . . ?
C13 C6 C11 O4 -177.98(12) . . . . ?
C17 C6 C11 C3 -168.32(12) . . . . ?
C1 C6 C11 C3 70.51(15) . . . . ?
C13 C6 C11 C3 -53.79(16) . . . . ?
C15 C5 C14 C18 0.3(2) . . . . ?
S1 C5 C14 C18 178.87(12) . . . . ?
C14 C5 C15 C21 -1.1(2) . . . . ?
S1 C5 C15 C21 -179.60(12) . . . . ?
C10 C3 C16 C20 2.0(2) . . . . ?
C11 C3 C16 C20 -177.17(14) . . . . ?
C1 C6 C17 F1 61.39(17) . . . . ?
C13 C6 C17 F1 -177.22(12) . . . . ?
C11 C6 C17 F1 -61.21(17) . . . . ?
C1 C6 C17 F3 -60.27(17) . . . . ?
C13 C6 C17 F3 61.12(16) . . . . ?
C11 C6 C17 F3 177.13(12) . . . . ?
C1 C6 C17 F2 -178.25(13) . . . . ?
C13 C6 C17 F2 -56.86(17) . . . . ?
C11 C6 C17 F2 59.15(17) . . . . ?
C5 C14 C18 C12 0.7(2) . . . . ?
C21 C12 C18 C14 -1.0(2) . . . . ?
C23 C12 C18 C14 178.36(15) . . . . ?
C22 C19 C20 C16 -1.3(3) . . . . ?
C3 C16 C20 C19 0.0(2) . . . . ?
C5 C15 C21 C12 0.8(2) . . . . ?
C18 C12 C21 C15 0.3(2) . . . . ?
C23 C12 C21 C15 -179.13(15) . . . . ?
C20 C19 C22 C10 0.7(3) . . . . ?
C3 C10 C22 C19 1.3(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
O4 H1 O2 0.84 2.49 3.1584(17) 136.8 3_666
C14 H11 O4 0.95 2.61 3.3291(19) 132.6 3_666
C15 H12 O1 0.95 2.51 3.4167(17) 159.7 3_766

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.038



