# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_wll9642
_database_code_depnum_ccdc_archive 'CCDC 2286029'
loop_
_audit_author_name
_audit_author_address
'Liangliang Wang'
;Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
China
;
_audit_update_record             
;
2023-08-01 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H27 F3 O3'
_chemical_formula_sum            'C25 H27 F3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         432.46
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      hexagonal
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'y, -x+y, z+1/6'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'

_cell_length_a                   17.6761(5)
_cell_length_b                   17.6761(5)
_cell_length_c                   12.4915(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3380.0(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      2.8867
_cell_measurement_theta_max      69.9879
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368

_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            37431
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_full        69.98
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4274
_reflns_number_gt                4244
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1770
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         4274
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1207P)²+2.4293P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.506
_refine_diff_density_min         -0.425
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1994 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C11 0.3177(4) 0.2818(4) 0.8460(4) 0.0418(12) Uani d . . . 1 . .
O O2 0.22829(17) 0.25839(18) 0.3396(2) 0.0253(6) Uani d . . . 1 . .
F F2 0.2412(3) 0.2092(3) 0.8853(3) 0.0828(14) Uani d . . . 1 . .
O O3 0.40954(19) 0.57548(17) 0.1066(3) 0.0282(7) Uani d . . . 1 . .
F F3 0.3729(4) 0.2613(4) 0.8795(3) 0.0905(17) Uani d . . . 1 . .
C C1 0.6764(3) 0.4602(3) 0.1941(5) 0.0441(14) Uani d . . . 1 . .
H H1 0.737252 0.481587 0.185704 0.053 Uiso calc U . R 1 . .
F F1 0.3096(4) 0.3413(3) 0.8945(3) 0.0851(16) Uani d . . . 1 . .
O O1 0.38140(16) 0.34175(17) 0.3413(2) 0.0183(5) Uani d . . . 1 . .
C C2 0.6437(3) 0.4705(3) 0.2899(5) 0.0392(12) Uani d . . . 1 . .
H H2 0.682055 0.498176 0.348434 0.047 Uiso calc U . R 1 . .
C C3 0.5553(3) 0.4409(3) 0.3010(4) 0.0262(8) Uani d . . . 1 . .
H H27 0.53403 0.449035 0.367314 0.031 Uiso calc U . R 1 . .
C C4 0.4970(3) 0.3993(2) 0.2173(3) 0.0218(8) Uani d . . . 1 . .
C C5 0.4004(2) 0.3735(2) 0.2318(3) 0.0187(7) Uani d . . . 1 . .
C C6 0.3025(2) 0.3284(3) 0.3891(3) 0.0217(8) Uani d . . . 1 . .
C C7 0.3076(3) 0.3096(3) 0.5066(3) 0.0237(8) Uani d . . . 1 . .
C C8 0.2331(3) 0.2806(4) 0.5696(4) 0.0383(12) Uani d . . . 1 . .
H H8 0.179698 0.268609 0.53688 0.046 Uiso calc U . R 1 . .
C C9 0.2352(3) 0.2689(4) 0.6788(4) 0.0442(13) Uani d . . . 1 . .
H H7 0.183527 0.248713 0.720295 0.053 Uiso calc U . R 1 . .
C C10 0.3122(3) 0.2867(3) 0.7273(4) 0.0328(10) Uani d . . . 1 . .
C C12 0.5295(4) 0.3868(3) 0.1205(4) 0.0357(11) Uani d . . . 1 . .
H H3 0.491103 0.357387 0.062525 0.043 Uiso calc U . R 1 . .
C C13 0.6192(4) 0.4180(4) 0.1104(5) 0.0484(15) Uani d . . . 1 . .
H H4 0.641292 0.410138 0.044533 0.058 Uiso calc U . R 1 . .
C C14 0.3879(3) 0.3151(3) 0.6652(3) 0.0254(8) Uani d . . . 1 . .
H H5 0.440992 0.326536 0.698375 0.031 Uiso calc U . R 1 . .
C C15 0.3855(3) 0.3266(3) 0.5557(3) 0.0223(8) Uani d . . . 1 . .
H H6 0.436888 0.346077 0.513982 0.027 Uiso calc U . R 1 . .
C C16 0.2280(3) 0.1768(3) 0.3413(4) 0.0298(9) Uani d . . . 1 . .
H H9 0.172625 0.130991 0.373125 0.036 Uiso calc U . R 1 . .
H H16 0.276717 0.182895 0.386499 0.036 Uiso calc U . R 1 . .
C C17 0.2376(3) 0.1494(3) 0.2282(4) 0.0326(10) Uani d . . . 1 . .
H H15 0.230809 0.090388 0.231587 0.039 Uiso calc U . R 1 . .
H H10 0.189728 0.145566 0.183137 0.039 Uiso calc U . R 1 . .
C C18 0.3246(3) 0.2111(3) 0.1744(3) 0.0303(9) Uani d . . . 1 . .
H H14 0.327708 0.185122 0.105507 0.036 Uiso calc U . R 1 . .
H H13 0.37258 0.216246 0.220356 0.036 Uiso calc U . R 1 . .
C C19 0.3393(3) 0.3029(2) 0.1530(3) 0.0236(8) Uani d . . . 1 . .
H H11 0.281937 0.300028 0.154405 0.028 Uiso calc U . R 1 . .
H H12 0.363486 0.320738 0.079959 0.028 Uiso calc U . R 1 . .
C C20 0.2929(3) 0.4096(3) 0.3783(3) 0.0251(8) Uani d . . . 1 . .
H H17 0.234043 0.395196 0.403298 0.03 Uiso calc U . R 1 . .
H H26 0.336364 0.456268 0.425172 0.03 Uiso calc U . R 1 . .
C C21 0.3055(2) 0.4435(3) 0.2648(3) 0.0231(8) Uani d . . . 1 . .
H H18 0.257215 0.39883 0.219368 0.028 Uiso calc U . R 1 . .
C C22 0.3055(3) 0.5300(3) 0.2557(4) 0.0280(9) Uani d . . . 1 . .
H H25 0.247245 0.520917 0.275057 0.034 Uiso calc U . R 1 . .
H H24 0.348959 0.573352 0.305833 0.034 Uiso calc U . R 1 . .
C C23 0.3282(3) 0.5645(3) 0.1411(4) 0.0295(9) Uani d . . . 1 . .
H H23 0.28158 0.52314 0.092341 0.035 Uiso calc U . R 1 . .
H H19 0.32997 0.621253 0.136505 0.035 Uiso calc U . R 1 . .
C C24 0.4085(3) 0.4940(2) 0.1084(3) 0.0236(8) Uani d . . . 1 . .
H H22 0.464976 0.502729 0.081337 0.028 Uiso calc U . R 1 . .
H H20 0.361658 0.451807 0.060706 0.028 Uiso calc U . R 1 . .
C C25 0.3932(2) 0.4571(2) 0.2219(3) 0.0197(7) Uani d . . . 1 . .
H H21 0.440123 0.50268 0.267964 0.024 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 F3 . 1.269(6) ?
C11 F1 . 1.283(6) ?
C11 F2 . 1.408(7) ?
C11 C10 . 1.492(7) ?
O2 C6 . 1.418(5) ?
O2 C16 . 1.439(5) ?
O3 C23 . 1.419(5) ?
O3 C24 . 1.431(4) ?
C1 C2 . 1.381(8) ?
C1 C13 . 1.385(9) ?
C1 H1 . 0.95 ?
O1 C6 . 1.425(4) ?
O1 C5 . 1.452(4) ?
C2 C3 . 1.384(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.393(6) ?
C3 H27 . 0.95 ?
C4 C12 . 1.404(6) ?
C4 C5 . 1.542(5) ?
C5 C19 . 1.532(5) ?
C5 C25 . 1.551(5) ?
C6 C7 . 1.518(5) ?
C6 C20 . 1.532(5) ?
C7 C8 . 1.394(6) ?
C7 C15 . 1.396(5) ?
C8 C9 . 1.383(7) ?
C8 H8 . 0.95 ?
C9 C10 . 1.376(7) ?
C9 H7 . 0.95 ?
C10 C14 . 1.404(6) ?
C12 C13 . 1.399(8) ?
C12 H3 . 0.95 ?
C13 H4 . 0.95 ?
C14 C15 . 1.388(6) ?
C14 H5 . 0.95 ?
C15 H6 . 0.95 ?
C16 C17 . 1.530(7) ?
C16 H9 . 0.99 ?
C16 H16 . 0.99 ?
C17 C18 . 1.526(7) ?
C17 H15 . 0.99 ?
C17 H10 . 0.99 ?
C18 C19 . 1.532(5) ?
C18 H14 . 0.99 ?
C18 H13 . 0.99 ?
C19 H11 . 0.99 ?
C19 H12 . 0.99 ?
C20 C21 . 1.512(6) ?
C20 H17 . 0.99 ?
C20 H26 . 0.99 ?
C21 C22 . 1.533(5) ?
C21 C25 . 1.541(5) ?
C21 H18 . 1.0 ?
C22 C23 . 1.528(7) ?
C22 H25 . 0.99 ?
C22 H24 . 0.99 ?
C23 H23 . 0.99 ?
C23 H19 . 0.99 ?
C24 C25 . 1.528(5) ?
C24 H22 . 0.99 ?
C24 H20 . 0.99 ?
C25 H21 . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F3 C11 F1 . . 119.7(6) ?
F3 C11 F2 . . 98.7(5) ?
F1 C11 F2 . . 97.6(5) ?
F3 C11 C10 . . 115.2(4) ?
F1 C11 C10 . . 112.6(4) ?
F2 C11 C10 . . 109.8(5) ?
C6 O2 C16 . . 114.0(3) ?
C23 O3 C24 . . 110.8(3) ?
C2 C1 C13 . . 118.9(4) ?
C2 C1 H1 . . 120.5 ?
C13 C1 H1 . . 120.5 ?
C6 O1 C5 . . 118.4(3) ?
C1 C2 C3 . . 120.4(5) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
C2 C3 C4 . . 121.5(4) ?
C2 C3 H27 . . 119.3 ?
C4 C3 H27 . . 119.3 ?
C3 C4 C12 . . 118.4(4) ?
C3 C4 C5 . . 119.1(3) ?
C12 C4 C5 . . 122.4(4) ?
O1 C5 C19 . . 111.0(3) ?
O1 C5 C4 . . 103.5(3) ?
C19 C5 C4 . . 113.0(3) ?
O1 C5 C25 . . 109.3(3) ?
C19 C5 C25 . . 111.4(3) ?
C4 C5 C25 . . 108.4(3) ?
O2 C6 O1 . . 111.3(3) ?
O2 C6 C7 . . 111.1(3) ?
O1 C6 C7 . . 106.3(3) ?
O2 C6 C20 . . 107.0(3) ?
O1 C6 C20 . . 111.5(3) ?
C7 C6 C20 . . 109.7(3) ?
C8 C7 C15 . . 118.7(4) ?
C8 C7 C6 . . 118.6(4) ?
C15 C7 C6 . . 122.6(3) ?
C9 C8 C7 . . 121.4(4) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C10 C9 C8 . . 119.8(4) ?
C10 C9 H7 . . 120.1 ?
C8 C9 H7 . . 120.1 ?
C9 C10 C14 . . 119.8(4) ?
C9 C10 C11 . . 120.7(5) ?
C14 C10 C11 . . 119.4(5) ?
C13 C12 C4 . . 119.3(5) ?
C13 C12 H3 . . 120.4 ?
C4 C12 H3 . . 120.4 ?
C1 C13 C12 . . 121.5(5) ?
C1 C13 H4 . . 119.2 ?
C12 C13 H4 . . 119.2 ?
C15 C14 C10 . . 120.2(4) ?
C15 C14 H5 . . 119.9 ?
C10 C14 H5 . . 119.9 ?
C14 C15 C7 . . 120.1(4) ?
C14 C15 H6 . . 120.0 ?
C7 C15 H6 . . 120.0 ?
O2 C16 C17 . . 111.0(3) ?
O2 C16 H9 . . 109.4 ?
C17 C16 H9 . . 109.4 ?
O2 C16 H16 . . 109.4 ?
C17 C16 H16 . . 109.4 ?
H9 C16 H16 . . 108.0 ?
C18 C17 C16 . . 114.3(4) ?
C18 C17 H15 . . 108.7 ?
C16 C17 H15 . . 108.7 ?
C18 C17 H10 . . 108.7 ?
C16 C17 H10 . . 108.7 ?
H15 C17 H10 . . 107.6 ?
C17 C18 C19 . . 114.2(4) ?
C17 C18 H14 . . 108.7 ?
C19 C18 H14 . . 108.7 ?
C17 C18 H13 . . 108.7 ?
C19 C18 H13 . . 108.7 ?
H14 C18 H13 . . 107.6 ?
C18 C19 C5 . . 115.3(3) ?
C18 C19 H11 . . 108.4 ?
C5 C19 H11 . . 108.4 ?
C18 C19 H12 . . 108.4 ?
C5 C19 H12 . . 108.4 ?
H11 C19 H12 . . 107.5 ?
C21 C20 C6 . . 113.0(3) ?
C21 C20 H17 . . 109.0 ?
C6 C20 H17 . . 109.0 ?
C21 C20 H26 . . 109.0 ?
C6 C20 H26 . . 109.0 ?
H17 C20 H26 . . 107.8 ?
C20 C21 C22 . . 113.1(3) ?
C20 C21 C25 . . 109.0(3) ?
C22 C21 C25 . . 108.7(3) ?
C20 C21 H18 . . 108.7 ?
C22 C21 H18 . . 108.7 ?
C25 C21 H18 . . 108.7 ?
C23 C22 C21 . . 109.6(4) ?
C23 C22 H25 . . 109.7 ?
C21 C22 H25 . . 109.7 ?
C23 C22 H24 . . 109.7 ?
C21 C22 H24 . . 109.7 ?
H25 C22 H24 . . 108.2 ?
O3 C23 C22 . . 112.6(3) ?
O3 C23 H23 . . 109.1 ?
C22 C23 H23 . . 109.1 ?
O3 C23 H19 . . 109.1 ?
C22 C23 H19 . . 109.1 ?
H23 C23 H19 . . 107.8 ?
O3 C24 C25 . . 110.8(3) ?
O3 C24 H22 . . 109.5 ?
C25 C24 H22 . . 109.5 ?
O3 C24 H20 . . 109.5 ?
C25 C24 H20 . . 109.5 ?
H22 C24 H20 . . 108.1 ?
C24 C25 C21 . . 109.8(3) ?
C24 C25 C5 . . 113.5(3) ?
C21 C25 C5 . . 112.3(3) ?
C24 C25 H21 . . 106.9 ?
C21 C25 H21 . . 106.9 ?
C5 C25 H21 . . 106.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C3 . . . . -1.4(7) ?
C1 C2 C3 C4 . . . . 0.6(7) ?
C2 C3 C4 C12 . . . . 0.9(6) ?
C2 C3 C4 C5 . . . . -175.7(4) ?
C6 O1 C5 C19 . . . . -70.9(4) ?
C6 O1 C5 C4 . . . . 167.7(3) ?
C6 O1 C5 C25 . . . . 52.3(4) ?
C3 C4 C5 O1 . . . . -40.2(4) ?
C12 C4 C5 O1 . . . . 143.4(4) ?
C3 C4 C5 C19 . . . . -160.3(3) ?
C12 C4 C5 C19 . . . . 23.3(5) ?
C3 C4 C5 C25 . . . . 75.8(4) ?
C12 C4 C5 C25 . . . . -100.7(4) ?
C16 O2 C6 O1 . . . . 56.9(4) ?
C16 O2 C6 C7 . . . . -61.3(4) ?
C16 O2 C6 C20 . . . . 179.0(3) ?
C5 O1 C6 O2 . . . . 67.7(4) ?
C5 O1 C6 C7 . . . . -171.3(3) ?
C5 O1 C6 C20 . . . . -51.8(4) ?
O2 C6 C7 C8 . . . . -48.9(5) ?
O1 C6 C7 C8 . . . . -170.2(4) ?
C20 C6 C7 C8 . . . . 69.2(5) ?
O2 C6 C7 C15 . . . . 136.2(4) ?
O1 C6 C7 C15 . . . . 15.0(5) ?
C20 C6 C7 C15 . . . . -105.6(4) ?
C15 C7 C8 C9 . . . . 0.3(8) ?
C6 C7 C8 C9 . . . . -174.8(5) ?
C7 C8 C9 C10 . . . . 0.5(9) ?
C8 C9 C10 C14 . . . . -1.1(8) ?
C8 C9 C10 C11 . . . . 174.8(5) ?
F3 C11 C10 C9 . . . . 150.4(6) ?
F1 C11 C10 C9 . . . . -67.4(8) ?
F2 C11 C10 C9 . . . . 40.2(6) ?
F3 C11 C10 C14 . . . . -33.6(8) ?
F1 C11 C10 C14 . . . . 108.6(6) ?
F2 C11 C10 C14 . . . . -143.9(4) ?
C3 C4 C12 C13 . . . . -1.5(6) ?
C5 C4 C12 C13 . . . . 175.0(4) ?
C2 C1 C13 C12 . . . . 0.7(7) ?
C4 C12 C13 C1 . . . . 0.7(7) ?
C9 C10 C14 C15 . . . . 1.0(7) ?
C11 C10 C14 C15 . . . . -175.0(4) ?
C10 C14 C15 C7 . . . . -0.3(6) ?
C8 C7 C15 C14 . . . . -0.4(6) ?
C6 C7 C15 C14 . . . . 174.5(4) ?
C6 O2 C16 C17 . . . . -112.9(4) ?
O2 C16 C17 C18 . . . . 64.4(5) ?
C16 C17 C18 C19 . . . . -64.6(5) ?
C17 C18 C19 C5 . . . . 102.0(4) ?
O1 C5 C19 C18 . . . . -43.7(5) ?
C4 C5 C19 C18 . . . . 72.0(4) ?
C25 C5 C19 C18 . . . . -165.7(4) ?
O2 C6 C20 C21 . . . . -70.9(4) ?
O1 C6 C20 C21 . . . . 51.0(4) ?
C7 C6 C20 C21 . . . . 168.5(3) ?
C6 C20 C21 C22 . . . . -173.9(3) ?
C6 C20 C21 C25 . . . . -53.0(4) ?
C20 C21 C22 C23 . . . . 174.0(3) ?
C25 C21 C22 C23 . . . . 53.0(4) ?
C24 O3 C23 C22 . . . . 60.8(4) ?
C21 C22 C23 O3 . . . . -56.9(4) ?
C23 O3 C24 C25 . . . . -61.4(4) ?
O3 C24 C25 C21 . . . . 59.0(4) ?
O3 C24 C25 C5 . . . . -174.3(3) ?
C20 C21 C25 C24 . . . . -178.3(3) ?
C22 C21 C25 C24 . . . . -54.7(4) ?
C20 C21 C25 C5 . . . . 54.3(4) ?
C22 C21 C25 C5 . . . . 177.9(3) ?
O1 C5 C25 C24 . . . . -177.8(3) ?
C19 C5 C25 C24 . . . . -54.8(4) ?
C4 C5 C25 C24 . . . . 70.1(4) ?
O1 C5 C25 C21 . . . . -52.4(4) ?
C19 C5 C25 C21 . . . . 70.6(4) ?
C4 C5 C25 C21 . . . . -164.5(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C19 H12 F1 1_554 0.99 2.60 3.394(5) 137.4 ?




####################################################################### 
# 
# 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_wj126
_database_code_depnum_ccdc_archive 'CCDC 2286031'
loop_
_audit_author_name
_audit_author_address
'Liangliang Wang'
;Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
China
;
_audit_update_record             
;
2023-08-01 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H25 F3 O3'
_chemical_formula_sum            'C24 H25 F3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         418.44
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6597(2)
_cell_length_b                   15.6244(4)
_cell_length_c                   13.1101(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.6180(10)
_cell_angle_gamma                90
_cell_volume                     2056.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      3.5791
_cell_measurement_theta_max      69.9785
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            51308
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         70.12
_diffrn_reflns_theta_full        70.12
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             7634
_reflns_number_gt                7213
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0753
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_refine_ls_number_reflns         7634
_refine_ls_number_parameters     541
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.3600P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3202 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.88891(15) 0.19314(10) 0.77557(13) 0.0307(3) Uani d . . . 1 . .
F F1 0.84092(19) 0.37462(14) 0.27182(13) 0.0651(6) Uani d . . . 1 . .
O O2 0.73380(14) 0.30031(10) 0.76732(12) 0.0259(3) Uani d . . . 1 . .
F F2 0.62930(18) 0.37365(12) 0.23146(12) 0.0543(4) Uani d . . . 1 . .
O O4 0.52651(14) 0.69907(10) -0.29085(12) 0.0280(3) Uani d . . . 1 . .
F F4 0.67092(19) 0.57962(15) 0.23284(14) 0.0663(6) Uani d . . . 1 . .
O O5 0.74218(14) 0.65442(9) -0.27390(12) 0.0246(3) Uani d . . . 1 . .
F F5 0.88050(18) 0.57232(12) 0.26266(13) 0.0556(4) Uani d . . . 1 . .
O O6 0.7747(2) 0.89546(12) -0.47558(15) 0.0451(4) Uani d . . . 1 . .
F F6 0.7931(2) 0.69053(13) 0.28279(13) 0.0603(5) Uani d . . . 1 . .
C C1 0.3651(3) 0.4187(2) 0.8668(2) 0.0437(6) Uani d . . . 1 . .
H H1 0.281944 0.442241 0.864252 0.052 Uiso calc U . R 1 . .
C C2 0.4704(3) 0.41681(19) 0.9631(2) 0.0436(6) Uani d . . . 1 . .
H H25 0.4599 0.439488 1.026951 0.052 Uiso calc U . R 1 . .
C C3 0.5916(2) 0.38185(17) 0.9670(2) 0.0365(5) Uani d . . . 1 . .
H H24 0.662918 0.379626 1.03399 0.044 Uiso calc U . R 1 . .
F F3 0.73276(18) 0.25812(11) 0.22360(12) 0.0508(4) Uani d . . . 1 . .
O O3 1.04396(17) 0.42575(12) 1.07193(14) 0.0403(4) Uani d . . . 1 . .
C C4 0.6100(2) 0.34991(15) 0.87348(18) 0.0283(5) Uani d . . . 1 . .
C C5 0.7442(2) 0.31072(14) 0.88026(17) 0.0250(4) Uani d . . . 1 . .
C C6 0.8478(2) 0.27705(14) 0.74064(18) 0.0269(5) Uani d . . . 1 . .
C C7 0.8070(2) 0.28536(15) 0.61780(18) 0.0270(5) Uani d . . . 1 . .
C C8 0.7128(2) 0.34458(15) 0.56099(19) 0.0315(5) Uani d . . . 1 . .
H H10 0.664793 0.376421 0.597503 0.038 Uiso calc U . R 1 . .
C C9 0.6877(2) 0.35790(16) 0.45131(19) 0.0327(5) Uani d . . . 1 . .
H H13 0.623035 0.398713 0.412799 0.039 Uiso calc U . R 1 . .
C C10 0.7580(2) 0.31099(16) 0.39828(19) 0.0307(5) Uani d . . . 1 . .
C C11 0.7397(3) 0.32905(18) 0.2823(2) 0.0379(6) Uani d . . . 1 . .
C C12 0.3815(3) 0.3863(2) 0.7744(2) 0.0421(6) Uani d . . . 1 . .
H H2 0.30898 0.386966 0.708044 0.051 Uiso calc U . R 1 . .
C C13 0.5036(2) 0.35254(17) 0.77741(19) 0.0337(5) Uani d . . . 1 . .
H H3 0.513972 0.331107 0.712891 0.04 Uiso calc U . R 1 . .
C C14 0.7617(2) 0.22442(15) 0.94088(18) 0.0301(5) Uani d . . . 1 . .
H H4 0.856083 0.206704 0.961094 0.036 Uiso calc U . R 1 . .
H H23 0.741899 0.233022 1.008738 0.036 Uiso calc U . R 1 . .
C C15 0.6739(3) 0.15174(16) 0.8768(2) 0.0365(5) Uani d . . . 1 . .
H H6 0.639614 0.118605 0.926186 0.044 Uiso calc U . R 1 . .
H H5 0.596423 0.176895 0.819849 0.044 Uiso calc U . R 1 . .
C C16 0.7452(3) 0.09055(17) 0.8236(2) 0.0428(6) Uani d . . . 1 . .
H H8 0.825476 0.068115 0.880194 0.051 Uiso calc U . R 1 . .
H H7 0.685643 0.041369 0.793593 0.051 Uiso calc U . R 1 . .
C C17 0.7870(3) 0.12898(16) 0.7340(2) 0.0386(6) Uani d . . . 1 . .
H H9 0.82113 0.083144 0.698171 0.046 Uiso calc U . R 1 . .
H H22 0.708632 0.155183 0.679052 0.046 Uiso calc U . R 1 . .
C C18 0.8495(2) 0.25040(16) 0.45328(19) 0.0327(5) Uani d . . . 1 . .
H H11 0.895276 0.217415 0.416039 0.039 Uiso calc U . R 1 . .
C C19 0.8748(2) 0.23750(16) 0.56313(19) 0.0318(5) Uani d . . . 1 . .
H H12 0.938468 0.195991 0.601139 0.038 Uiso calc U . R 1 . .
C C20 0.9671(2) 0.33583(15) 0.79366(18) 0.0289(5) Uani d . . . 1 . .
H H20 1.047921 0.312022 0.783053 0.035 Uiso calc U . R 1 . .
H H21 0.950116 0.393204 0.759756 0.035 Uiso calc U . R 1 . .
C C21 0.9884(2) 0.34302(15) 0.91381(18) 0.0295(5) Uani d . . . 1 . .
H H19 1.013191 0.285522 0.948176 0.035 Uiso calc U . R 1 . .
C C22 1.0857(2) 0.40896(18) 0.98023(19) 0.0361(5) Uani d . . . 1 . .
H H18 1.1778 0.386338 1.004012 0.043 Uiso calc U . R 1 . .
H H14 1.082061 0.461817 0.937676 0.043 Uiso calc U . R 1 . .
C C23 0.9126(2) 0.39056(17) 1.05216(19) 0.0339(5) Uani d . . . 1 . .
H H16 0.854864 0.431953 1.072606 0.041 Uiso calc U . R 1 . .
H H15 0.917279 0.33702 1.093647 0.041 Uiso calc U . R 1 . .
C C24 0.8602(2) 0.37316(15) 0.93068(17) 0.0272(4) Uani d . . . 1 . .
H H17 0.835198 0.429438 0.893004 0.033 Uiso calc U . R 1 . .
C C25 1.0911(3) 0.52165(18) -0.3831(2) 0.0423(6) Uani d . . . 1 . .
H H26 1.167914 0.490927 -0.383302 0.051 Uiso calc U . R 1 . .
C C26 0.9778(3) 0.52049(18) -0.4727(2) 0.0420(6) Uani d . . . 1 . .
H H44 0.975899 0.488168 -0.534595 0.05 Uiso calc U . R 1 . .
C C27 0.8656(2) 0.56650(17) -0.4733(2) 0.0348(5) Uani d . . . 1 . .
H H45 0.787992 0.565563 -0.535882 0.042 Uiso calc U . R 1 . .
C C28 0.8658(2) 0.61378(14) -0.38341(17) 0.0260(4) Uani d . . . 1 . .
C C29 0.7487(2) 0.67022(14) -0.38188(17) 0.0243(4) Uani d . . . 1 . .
C C30 0.6640(2) 0.70861(14) -0.23280(17) 0.0248(4) Uani d . . . 1 . .
C C31 0.6964(2) 0.68293(14) -0.11413(18) 0.0267(5) Uani d . . . 1 . .
C C32 0.6126(2) 0.71216(17) -0.0595(2) 0.0355(5) Uani d . . . 1 . .
H H28 0.536793 0.745684 -0.096906 0.043 Uiso calc U . R 1 . .
C C33 0.6390(2) 0.69281(18) 0.04839(19) 0.0369(5) Uani d . . . 1 . .
H H27 0.581848 0.713334 0.085064 0.044 Uiso calc U . R 1 . .
C C34 0.7493(2) 0.64327(16) 0.10338(19) 0.0317(5) Uani d . . . 1 . .
C C35 0.7736(3) 0.62155(18) 0.2192(2) 0.0383(6) Uani d . . . 1 . .
C C36 0.6959(2) 0.80399(15) -0.24029(19) 0.0289(5) Uani d . . . 1 . .
H H29 0.629899 0.839631 -0.221661 0.035 Uiso calc U . R 1 . .
H H48 0.785331 0.817091 -0.188186 0.035 Uiso calc U . R 1 . .
C C37 0.6920(2) 0.82445(14) -0.35447(18) 0.0284(5) Uani d . . . 1 . .
H H47 0.599303 0.815988 -0.405825 0.034 Uiso calc U . R 1 . .
C C38 0.7862(2) 0.76415(15) -0.38501(18) 0.0270(5) Uani d . . . 1 . .
H H46 0.876715 0.771954 -0.329892 0.032 Uiso calc U . R 1 . .
C C39 0.7887(3) 0.80510(16) -0.4900(2) 0.0354(5) Uani d . . . 1 . .
H H31 0.873763 0.792645 -0.501909 0.042 Uiso calc U . R 1 . .
H H30 0.714307 0.78351 -0.552673 0.042 Uiso calc U . R 1 . .
C C40 0.7443(3) 0.90957(16) -0.3773(2) 0.0374(5) Uani d . . . 1 . .
H H33 0.676255 0.954915 -0.38798 0.045 Uiso calc U . R 1 . .
H H32 0.825255 0.926366 -0.317006 0.045 Uiso calc U . R 1 . .
C C41 0.6175(2) 0.64808(15) -0.47099(18) 0.0298(5) Uani d . . . 1 . .
H H41 0.633838 0.644221 -0.54087 0.036 Uiso calc U . R 1 . .
H H34 0.553509 0.695285 -0.476955 0.036 Uiso calc U . R 1 . .
C C42 0.5540(2) 0.56394(16) -0.4521(2) 0.0349(5) Uani d . . . 1 . .
H H36 0.521242 0.532044 -0.521303 0.042 Uiso calc U . R 1 . .
H H35 0.623277 0.528548 -0.399944 0.042 Uiso calc U . R 1 . .
C C43 0.4383(2) 0.57642(17) -0.4090(2) 0.0374(6) Uani d . . . 1 . .
H H38 0.372493 0.615498 -0.458449 0.045 Uiso calc U . R 1 . .
H H37 0.39397 0.520542 -0.410546 0.045 Uiso calc U . R 1 . .
C C44 0.4779(2) 0.61226(16) -0.2951(2) 0.0337(5) Uani d . . . 1 . .
H H39 0.399889 0.611241 -0.270234 0.04 Uiso calc U . R 1 . .
H H40 0.548152 0.575794 -0.245617 0.04 Uiso calc U . R 1 . .
C C45 1.0929(2) 0.56779(18) -0.2924(2) 0.0393(6) Uani d . . . 1 . .
H H42 1.170666 0.568176 -0.229896 0.047 Uiso calc U . R 1 . .
C C46 0.9812(2) 0.61340(16) -0.29276(19) 0.0312(5) Uani d . . . 1 . .
H H43 0.98335 0.644917 -0.230241 0.037 Uiso calc U . R 1 . .
C C47 0.8077(2) 0.63467(15) -0.05784(19) 0.0295(5) Uani d . . . 1 . .
H H49 0.86605 0.615025 -0.093926 0.035 Uiso calc U . R 1 . .
C C48 0.8343(2) 0.61496(16) 0.05052(19) 0.0324(5) Uani d . . . 1 . .
H H50 0.910694 0.582073 0.088433 0.039 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.409(3) ?
O1 C17 . 1.444(3) ?
F1 C11 . 1.338(3) ?
O2 C6 . 1.420(2) ?
O2 C5 . 1.456(2) ?
F2 C11 . 1.337(3) ?
O4 C30 . 1.414(3) ?
O4 C44 . 1.446(3) ?
F4 C35 . 1.338(3) ?
O5 C30 . 1.415(2) ?
O5 C29 . 1.462(2) ?
F5 C35 . 1.334(3) ?
O6 C39 . 1.439(3) ?
O6 C40 . 1.447(3) ?
F6 C35 . 1.336(3) ?
C1 C12 . 1.378(4) ?
C1 C2 . 1.379(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.388(3) ?
C2 H25 . 0.95 ?
C3 C4 . 1.397(3) ?
C3 H24 . 0.95 ?
F3 C11 . 1.337(3) ?
O3 C22 . 1.439(3) ?
O3 C23 . 1.444(3) ?
C4 C13 . 1.384(3) ?
C4 C5 . 1.530(3) ?
C5 C24 . 1.540(3) ?
C5 C14 . 1.544(3) ?
C6 C7 . 1.526(3) ?
C6 C20 . 1.533(3) ?
C7 C8 . 1.385(3) ?
C7 C19 . 1.394(3) ?
C8 C9 . 1.387(3) ?
C8 H10 . 0.95 ?
C9 C10 . 1.390(3) ?
C9 H13 . 0.95 ?
C10 C18 . 1.377(4) ?
C10 C11 . 1.493(3) ?
C12 C13 . 1.392(3) ?
C12 H2 . 0.95 ?
C13 H3 . 0.95 ?
C14 C15 . 1.531(3) ?
C14 H4 . 0.99 ?
C14 H23 . 0.99 ?
C15 C16 . 1.528(3) ?
C15 H6 . 0.99 ?
C15 H5 . 0.99 ?
C16 C17 . 1.514(4) ?
C16 H8 . 0.99 ?
C16 H7 . 0.99 ?
C17 H9 . 0.99 ?
C17 H22 . 0.99 ?
C18 C19 . 1.388(3) ?
C18 H11 . 0.95 ?
C19 H12 . 0.95 ?
C20 C21 . 1.518(3) ?
C20 H20 . 0.99 ?
C20 H21 . 0.99 ?
C21 C22 . 1.513(3) ?
C21 C24 . 1.529(3) ?
C21 H19 . 1.0 ?
C22 H18 . 0.99 ?
C22 H14 . 0.99 ?
C23 C24 . 1.525(3) ?
C23 H16 . 0.99 ?
C23 H15 . 0.99 ?
C24 H17 . 1.0 ?
C25 C26 . 1.374(4) ?
C25 C45 . 1.385(4) ?
C25 H26 . 0.95 ?
C26 C27 . 1.393(3) ?
C26 H44 . 0.95 ?
C27 C28 . 1.390(3) ?
C27 H45 . 0.95 ?
C28 C46 . 1.394(3) ?
C28 C29 . 1.534(3) ?
C29 C38 . 1.525(3) ?
C29 C41 . 1.531(3) ?
C30 C31 . 1.530(3) ?
C30 C36 . 1.539(3) ?
C31 C47 . 1.390(3) ?
C31 C32 . 1.396(3) ?
C32 C33 . 1.380(3) ?
C32 H28 . 0.95 ?
C33 C34 . 1.390(4) ?
C33 H27 . 0.95 ?
C34 C48 . 1.385(3) ?
C34 C35 . 1.491(3) ?
C36 C37 . 1.517(3) ?
C36 H29 . 0.99 ?
C36 H48 . 0.99 ?
C37 C40 . 1.511(3) ?
C37 C38 . 1.525(3) ?
C37 H47 . 1.0 ?
C38 C39 . 1.526(3) ?
C38 H46 . 1.0 ?
C39 H31 . 0.99 ?
C39 H30 . 0.99 ?
C40 H33 . 0.99 ?
C40 H32 . 0.99 ?
C41 C42 . 1.536(3) ?
C41 H41 . 0.99 ?
C41 H34 . 0.99 ?
C42 C43 . 1.531(3) ?
C42 H36 . 0.99 ?
C42 H35 . 0.99 ?
C43 C44 . 1.516(3) ?
C43 H38 . 0.99 ?
C43 H37 . 0.99 ?
C44 H39 . 0.99 ?
C44 H40 . 0.99 ?
C45 C46 . 1.386(3) ?
C45 H42 . 0.95 ?
C46 H43 . 0.95 ?
C47 C48 . 1.387(3) ?
C47 H49 . 0.95 ?
C48 H50 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C17 . . 114.25(18) ?
C6 O2 C5 . . 119.99(16) ?
C30 O4 C44 . . 114.38(17) ?
C30 O5 C29 . . 119.56(16) ?
C39 O6 C40 . . 109.28(18) ?
C12 C1 C2 . . 119.5(2) ?
C12 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H25 . . 119.9 ?
C3 C2 H25 . . 119.9 ?
C2 C3 C4 . . 120.8(2) ?
C2 C3 H24 . . 119.6 ?
C4 C3 H24 . . 119.6 ?
C22 O3 C23 . . 109.50(17) ?
C13 C4 C3 . . 118.3(2) ?
C13 C4 C5 . . 121.94(19) ?
C3 C4 C5 . . 119.7(2) ?
O2 C5 C4 . . 103.60(17) ?
O2 C5 C24 . . 106.44(16) ?
C4 C5 C24 . . 111.83(18) ?
O2 C5 C14 . . 112.36(18) ?
C4 C5 C14 . . 109.18(17) ?
C24 C5 C14 . . 113.04(18) ?
O1 C6 O2 . . 110.89(17) ?
O1 C6 C7 . . 111.68(18) ?
O2 C6 C7 . . 105.89(17) ?
O1 C6 C20 . . 106.84(18) ?
O2 C6 C20 . . 112.54(18) ?
C7 C6 C20 . . 109.07(18) ?
C8 C7 C19 . . 119.3(2) ?
C8 C7 C6 . . 121.53(19) ?
C19 C7 C6 . . 118.9(2) ?
C7 C8 C9 . . 120.7(2) ?
C7 C8 H10 . . 119.6 ?
C9 C8 H10 . . 119.6 ?
C8 C9 C10 . . 119.4(2) ?
C8 C9 H13 . . 120.3 ?
C10 C9 H13 . . 120.3 ?
C18 C10 C9 . . 120.5(2) ?
C18 C10 C11 . . 119.4(2) ?
C9 C10 C11 . . 120.1(2) ?
F2 C11 F3 . . 106.0(2) ?
F2 C11 F1 . . 106.0(2) ?
F3 C11 F1 . . 105.8(2) ?
F2 C11 C10 . . 113.5(2) ?
F3 C11 C10 . . 113.1(2) ?
F1 C11 C10 . . 111.8(2) ?
C1 C12 C13 . . 120.5(2) ?
C1 C12 H2 . . 119.8 ?
C13 C12 H2 . . 119.8 ?
C4 C13 C12 . . 120.7(2) ?
C4 C13 H3 . . 119.7 ?
C12 C13 H3 . . 119.7 ?
C15 C14 C5 . . 114.78(19) ?
C15 C14 H4 . . 108.6 ?
C5 C14 H4 . . 108.6 ?
C15 C14 H23 . . 108.6 ?
C5 C14 H23 . . 108.6 ?
H4 C14 H23 . . 107.5 ?
C16 C15 C14 . . 114.1(2) ?
C16 C15 H6 . . 108.7 ?
C14 C15 H6 . . 108.7 ?
C16 C15 H5 . . 108.7 ?
C14 C15 H5 . . 108.7 ?
H6 C15 H5 . . 107.6 ?
C17 C16 C15 . . 115.3(2) ?
C17 C16 H8 . . 108.4 ?
C15 C16 H8 . . 108.4 ?
C17 C16 H7 . . 108.4 ?
C15 C16 H7 . . 108.4 ?
H8 C16 H7 . . 107.5 ?
O1 C17 C16 . . 111.3(2) ?
O1 C17 H9 . . 109.4 ?
C16 C17 H9 . . 109.4 ?
O1 C17 H22 . . 109.4 ?
C16 C17 H22 . . 109.4 ?
H9 C17 H22 . . 108.0 ?
C10 C18 C19 . . 120.0(2) ?
C10 C18 H11 . . 120.0 ?
C19 C18 H11 . . 120.0 ?
C18 C19 C7 . . 120.1(2) ?
C18 C19 H12 . . 119.9 ?
C7 C19 H12 . . 119.9 ?
C21 C20 C6 . . 109.07(18) ?
C21 C20 H20 . . 109.9 ?
C6 C20 H20 . . 109.9 ?
C21 C20 H21 . . 109.9 ?
C6 C20 H21 . . 109.9 ?
H20 C20 H21 . . 108.3 ?
C22 C21 C20 . . 118.81(19) ?
C22 C21 C24 . . 100.39(19) ?
C20 C21 C24 . . 110.09(18) ?
C22 C21 H19 . . 109.0 ?
C20 C21 H19 . . 109.0 ?
C24 C21 H19 . . 109.0 ?
O3 C22 C21 . . 105.07(18) ?
O3 C22 H18 . . 110.7 ?
C21 C22 H18 . . 110.7 ?
O3 C22 H14 . . 110.7 ?
C21 C22 H14 . . 110.7 ?
H18 C22 H14 . . 108.8 ?
O3 C23 C24 . . 104.39(17) ?
O3 C23 H16 . . 110.9 ?
C24 C23 H16 . . 110.9 ?
O3 C23 H15 . . 110.9 ?
C24 C23 H15 . . 110.9 ?
H16 C23 H15 . . 108.9 ?
C23 C24 C21 . . 100.03(18) ?
C23 C24 C5 . . 121.41(18) ?
C21 C24 C5 . . 111.76(18) ?
C23 C24 H17 . . 107.6 ?
C21 C24 H17 . . 107.6 ?
C5 C24 H17 . . 107.6 ?
C26 C25 C45 . . 119.7(2) ?
C26 C25 H26 . . 120.1 ?
C45 C25 H26 . . 120.1 ?
C25 C26 C27 . . 120.3(2) ?
C25 C26 H44 . . 119.9 ?
C27 C26 H44 . . 119.9 ?
C28 C27 C26 . . 120.8(2) ?
C28 C27 H45 . . 119.6 ?
C26 C27 H45 . . 119.6 ?
C27 C28 C46 . . 118.1(2) ?
C27 C28 C29 . . 123.1(2) ?
C46 C28 C29 . . 118.70(19) ?
O5 C29 C38 . . 106.66(16) ?
O5 C29 C41 . . 111.88(16) ?
C38 C29 C41 . . 112.17(18) ?
O5 C29 C28 . . 102.66(16) ?
C38 C29 C28 . . 109.34(17) ?
C41 C29 C28 . . 113.52(18) ?
O4 C30 O5 . . 111.60(17) ?
O4 C30 C31 . . 111.04(16) ?
O5 C30 C31 . . 105.63(17) ?
O4 C30 C36 . . 106.20(18) ?
O5 C30 C36 . . 112.58(16) ?
C31 C30 C36 . . 109.86(18) ?
C47 C31 C32 . . 118.9(2) ?
C47 C31 C30 . . 122.90(19) ?
C32 C31 C30 . . 118.1(2) ?
C33 C32 C31 . . 120.6(2) ?
C33 C32 H28 . . 119.7 ?
C31 C32 H28 . . 119.7 ?
C32 C33 C34 . . 120.0(2) ?
C32 C33 H27 . . 120.0 ?
C34 C33 H27 . . 120.0 ?
C48 C34 C33 . . 120.0(2) ?
C48 C34 C35 . . 121.2(2) ?
C33 C34 C35 . . 118.8(2) ?
F5 C35 F6 . . 105.5(2) ?
F5 C35 F4 . . 106.3(2) ?
F6 C35 F4 . . 106.0(2) ?
F5 C35 C34 . . 113.4(2) ?
F6 C35 C34 . . 112.9(2) ?
F4 C35 C34 . . 112.2(2) ?
C37 C36 C30 . . 109.48(18) ?
C37 C36 H29 . . 109.8 ?
C30 C36 H29 . . 109.8 ?
C37 C36 H48 . . 109.8 ?
C30 C36 H48 . . 109.8 ?
H29 C36 H48 . . 108.2 ?
C40 C37 C36 . . 119.4(2) ?
C40 C37 C38 . . 99.91(18) ?
C36 C37 C38 . . 109.04(18) ?
C40 C37 H47 . . 109.3 ?
C36 C37 H47 . . 109.3 ?
C38 C37 H47 . . 109.3 ?
C29 C38 C37 . . 112.70(17) ?
C29 C38 C39 . . 120.78(19) ?
C37 C38 C39 . . 100.96(18) ?
C29 C38 H46 . . 107.2 ?
C37 C38 H46 . . 107.2 ?
C39 C38 H46 . . 107.2 ?
O6 C39 C38 . . 105.02(19) ?
O6 C39 H31 . . 110.7 ?
C38 C39 H31 . . 110.7 ?
O6 C39 H30 . . 110.7 ?
C38 C39 H30 . . 110.7 ?
H31 C39 H30 . . 108.8 ?
O6 C40 C37 . . 104.5(2) ?
O6 C40 H33 . . 110.8 ?
C37 C40 H33 . . 110.8 ?
O6 C40 H32 . . 110.8 ?
C37 C40 H32 . . 110.8 ?
H33 C40 H32 . . 108.9 ?
C29 C41 C42 . . 114.19(19) ?
C29 C41 H41 . . 108.7 ?
C42 C41 H41 . . 108.7 ?
C29 C41 H34 . . 108.7 ?
C42 C41 H34 . . 108.7 ?
H41 C41 H34 . . 107.6 ?
C43 C42 C41 . . 113.8(2) ?
C43 C42 H36 . . 108.8 ?
C41 C42 H36 . . 108.8 ?
C43 C42 H35 . . 108.8 ?
C41 C42 H35 . . 108.8 ?
H36 C42 H35 . . 107.7 ?
C44 C43 C42 . . 114.7(2) ?
C44 C43 H38 . . 108.6 ?
C42 C43 H38 . . 108.6 ?
C44 C43 H37 . . 108.6 ?
C42 C43 H37 . . 108.6 ?
H38 C43 H37 . . 107.6 ?
O4 C44 C43 . . 111.21(19) ?
O4 C44 H39 . . 109.4 ?
C43 C44 H39 . . 109.4 ?
O4 C44 H40 . . 109.4 ?
C43 C44 H40 . . 109.4 ?
H39 C44 H40 . . 108.0 ?
C25 C45 C46 . . 120.0(2) ?
C25 C45 H42 . . 120.0 ?
C46 C45 H42 . . 120.0 ?
C45 C46 C28 . . 121.1(2) ?
C45 C46 H43 . . 119.5 ?
C28 C46 H43 . . 119.5 ?
C48 C47 C31 . . 120.6(2) ?
C48 C47 H49 . . 119.7 ?
C31 C47 H49 . . 119.7 ?
C34 C48 C47 . . 119.9(2) ?
C34 C48 H50 . . 120.0 ?
C47 C48 H50 . . 120.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 C1 C2 C3 . . . . -0.5(5) ?
C1 C2 C3 C4 . . . . 1.4(4) ?
C2 C3 C4 C13 . . . . -1.2(4) ?
C2 C3 C4 C5 . . . . -179.3(2) ?
C6 O2 C5 C4 . . . . 170.67(17) ?
C6 O2 C5 C24 . . . . 52.6(2) ?
C6 O2 C5 C14 . . . . -71.6(2) ?
C13 C4 C5 O2 . . . . 12.4(3) ?
C3 C4 C5 O2 . . . . -169.6(2) ?
C13 C4 C5 C24 . . . . 126.6(2) ?
C3 C4 C5 C24 . . . . -55.4(3) ?
C13 C4 C5 C14 . . . . -107.5(2) ?
C3 C4 C5 C14 . . . . 70.5(3) ?
C17 O1 C6 O2 . . . . 56.2(2) ?
C17 O1 C6 C7 . . . . -61.6(2) ?
C17 O1 C6 C20 . . . . 179.22(17) ?
C5 O2 C6 O1 . . . . 67.2(2) ?
C5 O2 C6 C7 . . . . -171.51(17) ?
C5 O2 C6 C20 . . . . -52.4(2) ?
O1 C6 C7 C8 . . . . 151.1(2) ?
O2 C6 C7 C8 . . . . 30.3(3) ?
C20 C6 C7 C8 . . . . -91.0(2) ?
O1 C6 C7 C19 . . . . -34.7(3) ?
O2 C6 C7 C19 . . . . -155.5(2) ?
C20 C6 C7 C19 . . . . 83.2(3) ?
C19 C7 C8 C9 . . . . -1.4(4) ?
C6 C7 C8 C9 . . . . 172.7(2) ?
C7 C8 C9 C10 . . . . 0.1(4) ?
C8 C9 C10 C18 . . . . 1.5(4) ?
C8 C9 C10 C11 . . . . -175.4(2) ?
C18 C10 C11 F2 . . . . 165.6(2) ?
C9 C10 C11 F2 . . . . -17.4(3) ?
C18 C10 C11 F3 . . . . 44.8(3) ?
C9 C10 C11 F3 . . . . -138.2(2) ?
C18 C10 C11 F1 . . . . -74.5(3) ?
C9 C10 C11 F1 . . . . 102.5(3) ?
C2 C1 C12 C13 . . . . -0.6(5) ?
C3 C4 C13 C12 . . . . 0.0(4) ?
C5 C4 C13 C12 . . . . 178.1(2) ?
C1 C12 C13 C4 . . . . 0.9(4) ?
O2 C5 C14 C15 . . . . -42.0(2) ?
C4 C5 C14 C15 . . . . 72.4(2) ?
C24 C5 C14 C15 . . . . -162.48(18) ?
C5 C14 C15 C16 . . . . 99.2(2) ?
C14 C15 C16 C17 . . . . -66.6(3) ?
C6 O1 C17 C16 . . . . -113.0(2) ?
C15 C16 C17 O1 . . . . 66.5(3) ?
C9 C10 C18 C19 . . . . -1.8(4) ?
C11 C10 C18 C19 . . . . 175.1(2) ?
C10 C18 C19 C7 . . . . 0.5(4) ?
C8 C7 C19 C18 . . . . 1.1(4) ?
C6 C7 C19 C18 . . . . -173.2(2) ?
O1 C6 C20 C21 . . . . -71.7(2) ?
O2 C6 C20 C21 . . . . 50.3(2) ?
C7 C6 C20 C21 . . . . 167.48(18) ?
C6 C20 C21 C22 . . . . -170.0(2) ?
C6 C20 C21 C24 . . . . -55.1(2) ?
C23 O3 C22 C21 . . . . -13.4(3) ?
C20 C21 C22 O3 . . . . 156.3(2) ?
C24 C21 C22 O3 . . . . 36.3(2) ?
C22 O3 C23 C24 . . . . -15.4(3) ?
O3 C23 C24 C21 . . . . 37.3(2) ?
O3 C23 C24 C5 . . . . 160.58(19) ?
C22 C21 C24 C23 . . . . -44.2(2) ?
C20 C21 C24 C23 . . . . -170.31(19) ?
C22 C21 C24 C5 . . . . -174.08(18) ?
C20 C21 C24 C5 . . . . 59.9(2) ?
O2 C5 C24 C23 . . . . -171.93(19) ?
C4 C5 C24 C23 . . . . 75.6(3) ?
C14 C5 C24 C23 . . . . -48.1(3) ?
O2 C5 C24 C21 . . . . -54.3(2) ?
C4 C5 C24 C21 . . . . -166.78(18) ?
C14 C5 C24 C21 . . . . 69.5(2) ?
C45 C25 C26 C27 . . . . 1.0(4) ?
C25 C26 C27 C28 . . . . -0.4(4) ?
C26 C27 C28 C46 . . . . -0.3(4) ?
C26 C27 C28 C29 . . . . 175.9(2) ?
C30 O5 C29 C38 . . . . 51.9(2) ?
C30 O5 C29 C41 . . . . -71.1(2) ?
C30 O5 C29 C28 . . . . 166.86(17) ?
C27 C28 C29 O5 . . . . 139.8(2) ?
C46 C28 C29 O5 . . . . -43.9(2) ?
C27 C28 C29 C38 . . . . -107.2(2) ?
C46 C28 C29 C38 . . . . 69.0(2) ?
C27 C28 C29 C41 . . . . 18.9(3) ?
C46 C28 C29 C41 . . . . -164.9(2) ?
C44 O4 C30 O5 . . . . 55.6(2) ?
C44 O4 C30 C31 . . . . -62.0(2) ?
C44 O4 C30 C36 . . . . 178.63(17) ?
C29 O5 C30 O4 . . . . 67.7(2) ?
C29 O5 C30 C31 . . . . -171.54(16) ?
C29 O5 C30 C36 . . . . -51.7(2) ?
O4 C30 C31 C47 . . . . 137.6(2) ?
O5 C30 C31 C47 . . . . 16.5(3) ?
C36 C30 C31 C47 . . . . -105.2(2) ?
O4 C30 C31 C32 . . . . -44.8(3) ?
O5 C30 C31 C32 . . . . -165.9(2) ?
C36 C30 C31 C32 . . . . 72.4(3) ?
C47 C31 C32 C33 . . . . -0.6(4) ?
C30 C31 C32 C33 . . . . -178.3(2) ?
C31 C32 C33 C34 . . . . -0.5(4) ?
C32 C33 C34 C48 . . . . 1.4(4) ?
C32 C33 C34 C35 . . . . -178.5(2) ?
C48 C34 C35 F5 . . . . -1.3(3) ?
C33 C34 C35 F5 . . . . 178.6(2) ?
C48 C34 C35 F6 . . . . 118.6(3) ?
C33 C34 C35 F6 . . . . -61.4(3) ?
C48 C34 C35 F4 . . . . -121.7(3) ?
C33 C34 C35 F4 . . . . 58.2(3) ?
O4 C30 C36 C37 . . . . -71.8(2) ?
O5 C30 C36 C37 . . . . 50.6(2) ?
C31 C30 C36 C37 . . . . 167.99(17) ?
C30 C36 C37 C40 . . . . -168.81(19) ?
C30 C36 C37 C38 . . . . -55.0(2) ?
O5 C29 C38 C37 . . . . -54.7(2) ?
C41 C29 C38 C37 . . . . 68.1(2) ?
C28 C29 C38 C37 . . . . -165.07(18) ?
O5 C29 C38 C39 . . . . -174.01(18) ?
C41 C29 C38 C39 . . . . -51.2(3) ?
C28 C29 C38 C39 . . . . 75.7(3) ?
C40 C37 C38 C29 . . . . -173.86(19) ?
C36 C37 C38 C29 . . . . 60.1(2) ?
C40 C37 C38 C39 . . . . -43.6(2) ?
C36 C37 C38 C39 . . . . -169.64(19) ?
C40 O6 C39 C38 . . . . -8.5(3) ?
C29 C38 C39 O6 . . . . 157.86(19) ?
C37 C38 C39 O6 . . . . 32.9(2) ?
C39 O6 C40 C37 . . . . -19.9(3) ?
C36 C37 C40 O6 . . . . 158.2(2) ?
C38 C37 C40 O6 . . . . 39.6(2) ?
O5 C29 C41 C42 . . . . -42.9(2) ?
C38 C29 C41 C42 . . . . -162.72(18) ?
C28 C29 C41 C42 . . . . 72.7(2) ?
C29 C41 C42 C43 . . . . 101.5(2) ?
C41 C42 C43 C44 . . . . -67.5(3) ?
C30 O4 C44 C43 . . . . -111.8(2) ?
C42 C43 C44 O4 . . . . 66.3(3) ?
C26 C25 C45 C46 . . . . -0.8(4) ?
C25 C45 C46 C28 . . . . 0.1(4) ?
C27 C28 C46 C45 . . . . 0.5(3) ?
C29 C28 C46 C45 . . . . -175.9(2) ?
C32 C31 C47 C48 . . . . 0.8(3) ?
C30 C31 C47 C48 . . . . 178.4(2) ?
C33 C34 C48 C47 . . . . -1.3(4) ?
C35 C34 C48 C47 . . . . 178.7(2) ?
C31 C47 C48 C34 . . . . 0.2(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C16 H8 O3 2_747 0.99 2.59 3.390(3) 138.2 ?
C36 H48 O3 2_756 0.99 2.58 3.474(3) 150.3 ?



