# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_exp_589
_audit_block_doi                 10.5517/ccdc.csd.cc2br34c
_database_code_depnum_ccdc_archive 'CCDC 2167152'
loop_
_audit_author_name
_audit_author_address
'Pavel Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-18 deposited with the CCDC.	2022-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            8-trifluoromethyl-4,5-epoxycaryophyllan-8-ol
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 F3 O2'
_chemical_formula_sum            'C15 H23 F3 O2'
_chemical_formula_weight         292.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.1970(11)
_cell_length_b                   9.8989(13)
_cell_length_c                   12.9485(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.482(19)
_cell_angle_gamma                90.00
_cell_volume                     775.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1073
_cell_measurement_theta_min      4.0910
_cell_measurement_theta_max      22.9070

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_min  0.21949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5101
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         31.05
_reflns_number_total             3828
_reflns_number_gt                2002
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.20(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(15)
_refine_ls_number_reflns         3828
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2341
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0051(5) 0.6299(3) 0.8544(2) 0.0647(8) Uani 1 1 d . . .
F1 F -0.1938(8) 0.8627(3) 0.7582(3) 0.1236(14) Uani 1 1 d . . .
C1 C -0.1717(6) 0.4499(4) 0.6673(3) 0.0496(8) Uani 1 1 d . . .
F2 F -0.2701(6) 0.8372(3) 0.9094(2) 0.1056(12) Uani 1 1 d . . .
O2 O -0.1492(8) 0.2109(3) 0.9365(3) 0.1092(15) Uani 1 1 d . . .
C2 C -0.2878(8) 0.3133(4) 0.6514(3) 0.0612(11) Uani 1 1 d . . .
H2A H -0.2648 0.2752 0.5856 0.073 Uiso 1 1 calc R . .
H2B H -0.4453 0.3288 0.6428 0.073 Uiso 1 1 calc R . .
F3 F -0.5168(7) 0.8004(3) 0.7683(3) 0.1152(14) Uani 1 1 d . . .
C3 C -0.2184(9) 0.2080(5) 0.7382(4) 0.0740(13) Uani 1 1 d . . .
H3A H -0.2833 0.1213 0.7140 0.089 Uiso 1 1 calc R . .
H3B H -0.0589 0.1981 0.7539 0.089 Uiso 1 1 calc R . .
C4 C -0.2929(9) 0.2497(5) 0.8367(3) 0.0759(14) Uani 1 1 d . . .
C5 C -0.1566(10) 0.3500(5) 0.9027(3) 0.0730(13) Uani 1 1 d . . .
C6 C -0.2510(10) 0.4573(6) 0.9625(3) 0.0847(15) Uani 1 1 d . . .
H6A H -0.1328 0.5009 1.0129 0.102 Uiso 1 1 calc R . .
H6B H -0.3518 0.4167 1.0013 0.102 Uiso 1 1 calc R . .
C7 C -0.3733(8) 0.5616(5) 0.8847(3) 0.0728(13) Uani 1 1 d . . .
H7A H -0.4343 0.6294 0.9244 0.087 Uiso 1 1 calc R . .
H7B H -0.4966 0.5170 0.8384 0.087 Uiso 1 1 calc R . .
C8 C -0.2352(7) 0.6348(4) 0.8150(3) 0.0558(9) Uani 1 1 d . . .
C9 C -0.2783(7) 0.5821(4) 0.6999(3) 0.0510(8) Uani 1 1 d . . .
C10 C -0.1686(9) 0.6575(4) 0.6209(3) 0.0676(11) Uani 1 1 d . . .
H10A H -0.2658 0.7216 0.5770 0.081 Uiso 1 1 calc R . .
H10B H -0.0291 0.6996 0.6535 0.081 Uiso 1 1 calc R . .
C11 C -0.1425(6) 0.5249(4) 0.5648(3) 0.0563(9) Uani 1 1 d . . .
C12 C 0.0778(9) 0.5007(7) 0.5346(4) 0.0921(16) Uani 1 1 d . . .
H12A H 0.0788 0.5454 0.4689 0.138 Uiso 1 1 calc R . .
H12B H 0.0992 0.4055 0.5269 0.138 Uiso 1 1 calc R . .
H12C H 0.1949 0.5359 0.5889 0.138 Uiso 1 1 calc R . .
C13 C -0.3287(8) 0.5025(6) 0.4692(3) 0.0764(14) Uani 1 1 d . . .
H13A H -0.3164 0.5663 0.4150 0.115 Uiso 1 1 calc R . .
H13B H -0.4680 0.5144 0.4891 0.115 Uiso 1 1 calc R . .
H13C H -0.3198 0.4124 0.4430 0.115 Uiso 1 1 calc R . .
C14 C -0.5346(11) 0.2311(7) 0.8349(5) 0.105(2) Uani 1 1 d . . .
H14A H -0.5649 0.2611 0.9009 0.157 Uiso 1 1 calc R . .
H14B H -0.5725 0.1373 0.8246 0.157 Uiso 1 1 calc R . .
H14C H -0.6208 0.2831 0.7781 0.157 Uiso 1 1 calc R . .
C15 C -0.3013(10) 0.7833(5) 0.8123(4) 0.0808(15) Uani 1 1 d . . .
H1 H -0.023(7) 0.436(4) 0.714(3) 0.054(10) Uiso 1 1 d . . .
H9 H -0.447(8) 0.586(5) 0.673(3) 0.068(12) Uiso 1 1 d . . .
H1A H 0.040(10) 0.651(7) 0.929(5) 0.11(2) Uiso 1 1 d . . .
H5 H -0.003(8) 0.367(5) 0.883(3) 0.068(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.408(5) . ?
O1 H1A 0.97(6) . ?
F1 C15 1.325(7) . ?
C1 C2 1.525(5) . ?
C1 C11 1.565(5) . ?
C1 C9 1.564(5) . ?
C1 H1 1.00(4) . ?
F2 C15 1.341(6) . ?
O2 C5 1.442(6) . ?
O2 C4 1.453(5) . ?
C2 C3 1.525(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
F3 C15 1.344(7) . ?
C3 C4 1.506(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.455(7) . ?
C4 C14 1.504(8) . ?
C5 C6 1.505(8) . ?
C5 H5 1.05(5) . ?
C6 C7 1.525(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.551(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C15 1.524(6) . ?
C8 C9 1.547(5) . ?
C9 C10 1.539(6) . ?
C9 H9 1.03(5) . ?
C10 C11 1.526(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.515(6) . ?
C11 C12 1.518(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1A 114(4) . . ?
C2 C1 C11 116.4(3) . . ?
C2 C1 C9 124.3(3) . . ?
C11 C1 C9 88.0(3) . . ?
C2 C1 H1 108(2) . . ?
C11 C1 H1 108(2) . . ?
C9 C1 H1 110(2) . . ?
C5 O2 C4 60.3(3) . . ?
C1 C2 C3 117.2(3) . . ?
C1 C2 H2A 108.0 . . ?
C3 C2 H2A 108.0 . . ?
C1 C2 H2B 108.0 . . ?
C3 C2 H2B 108.0 . . ?
H2A C2 H2B 107.2 . . ?
C4 C3 C2 110.3(4) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O2 C4 C5 59.4(3) . . ?
O2 C4 C3 116.1(5) . . ?
C5 C4 C3 116.1(5) . . ?
O2 C4 C14 113.5(5) . . ?
C5 C4 C14 122.9(6) . . ?
C3 C4 C14 116.1(4) . . ?
O2 C5 C4 60.2(3) . . ?
O2 C5 C6 120.5(4) . . ?
C4 C5 C6 122.9(5) . . ?
O2 C5 H5 105(3) . . ?
C4 C5 H5 114(3) . . ?
C6 C5 H5 119(3) . . ?
C5 C6 C7 109.4(4) . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C6 C7 C8 116.2(4) . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
C8 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 C15 106.7(4) . . ?
O1 C8 C9 106.8(3) . . ?
C15 C8 C9 108.3(3) . . ?
O1 C8 C7 114.6(3) . . ?
C15 C8 C7 106.5(4) . . ?
C9 C8 C7 113.6(3) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 C1 87.3(3) . . ?
C8 C9 C1 123.2(3) . . ?
C10 C9 H9 109(2) . . ?
C8 C9 H9 105(2) . . ?
C1 C9 H9 113(3) . . ?
C11 C10 C9 90.4(3) . . ?
C11 C10 H10A 113.6 . . ?
C9 C10 H10A 113.6 . . ?
C11 C10 H10B 113.6 . . ?
C9 C10 H10B 113.6 . . ?
H10A C10 H10B 110.8 . . ?
C13 C11 C12 109.6(4) . . ?
C13 C11 C10 112.0(4) . . ?
C12 C11 C10 116.9(4) . . ?
C13 C11 C1 114.6(3) . . ?
C12 C11 C1 114.8(4) . . ?
C10 C11 C1 87.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 C15 F2 105.8(5) . . ?
F1 C15 F3 105.6(5) . . ?
F2 C15 F3 106.0(4) . . ?
F1 C15 C8 114.9(5) . . ?
F2 C15 C8 112.3(4) . . ?
F3 C15 C8 111.6(4) . . ?

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
C11 C1 C2 C3 148.6(4) . . . . ?
C9 C1 C2 C3 -104.5(5) . . . . ?
C1 C2 C3 C4 69.3(5) . . . . ?
C5 O2 C4 C3 106.2(5) . . . . ?
C5 O2 C4 C14 -115.5(6) . . . . ?
C2 C3 C4 O2 -146.7(4) . . . . ?
C2 C3 C4 C5 -79.7(5) . . . . ?
C2 C3 C4 C14 76.1(6) . . . . ?
C4 O2 C5 C6 112.8(6) . . . . ?
C3 C4 C5 O2 -106.2(5) . . . . ?
C14 C4 C5 O2 99.8(5) . . . . ?
O2 C4 C5 C6 -109.1(5) . . . . ?
C3 C4 C5 C6 144.6(4) . . . . ?
C14 C4 C5 C6 -9.4(7) . . . . ?
O2 C5 C6 C7 -143.9(5) . . . . ?
C4 C5 C6 C7 -71.7(6) . . . . ?
C5 C6 C7 C8 -58.6(6) . . . . ?
C6 C7 C8 O1 -19.8(5) . . . . ?
C6 C7 C8 C15 -137.6(4) . . . . ?
C6 C7 C8 C9 103.3(4) . . . . ?
O1 C8 C9 C10 -59.0(4) . . . . ?
C15 C8 C9 C10 55.6(5) . . . . ?
C7 C8 C9 C10 173.7(4) . . . . ?
O1 C8 C9 C1 47.4(5) . . . . ?
C15 C8 C9 C1 162.0(4) . . . . ?
C7 C8 C9 C1 -79.9(5) . . . . ?
C2 C1 C9 C10 -139.8(4) . . . . ?
C11 C1 C9 C10 -18.9(3) . . . . ?
C2 C1 C9 C8 98.3(5) . . . . ?
C11 C1 C9 C8 -140.8(4) . . . . ?
C8 C9 C10 C11 145.9(3) . . . . ?
C1 C9 C10 C11 19.4(3) . . . . ?
C9 C10 C11 C13 96.3(4) . . . . ?
C9 C10 C11 C12 -136.1(4) . . . . ?
C9 C10 C11 C1 -19.4(3) . . . . ?
C2 C1 C11 C13 33.6(5) . . . . ?
C9 C1 C11 C13 -94.1(4) . . . . ?
C2 C1 C11 C12 -94.5(5) . . . . ?
C9 C1 C11 C12 137.8(4) . . . . ?
C2 C1 C11 C10 146.8(4) . . . . ?
C9 C1 C11 C10 19.1(3) . . . . ?
O1 C8 C15 F1 55.3(6) . . . . ?
C9 C8 C15 F1 -59.3(6) . . . . ?
C7 C8 C15 F1 178.1(4) . . . . ?
O1 C8 C15 F2 -65.7(6) . . . . ?
C9 C8 C15 F2 179.7(4) . . . . ?
C7 C8 C15 F2 57.1(6) . . . . ?
O1 C8 C15 F3 175.4(4) . . . . ?
C9 C8 C15 F3 60.8(6) . . . . ?
C7 C8 C15 F3 -61.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.866
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_W-829
_database_code_depnum_ccdc_archive 'CCDC 2169284'
loop_
_audit_author_name
_audit_author_address
'Roman Rumyantcev'
;IOMC RAS
Russia
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H27 F3 O2'
_chemical_formula_weight         320.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   22.1155(11)
_cell_length_b                   8.7469(4)
_cell_length_c                   8.9710(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.7503(15)
_cell_angle_gamma                90
_cell_volume                     1692.58(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.63

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8638
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source\^A                \^A
_diffrn_measurement_device_type  Â
_diffrn_measurement_method\^A    \^A
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12825
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.513
_diffrn_reflns_theta_max         26.350
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3463
_reflns_number_gt                2937
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       APEX3
_computing_cell_refinement\^A    Â
_computing_data_reduction        Â
_computing_structure_solution    Â
_computing_structure_refinement  Â
_computing_molecular_graphics    Â
_computing_publication_material  Â
_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)+(0.0448P)²+0.3647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(19)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3463
_refine_ls_number_parameters     207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38196(8) 0.8541(2) 0.63224(19) 0.0516(4) Uani 1 1 d . . . . .
O2 O 0.32202(8) 0.14612(19) 0.6058(2) 0.0470(4) Uani 1 1 d . . . . .
H1 H 0.3471(14) 0.081(4) 0.608(3) 0.056 Uiso 1 1 d . U . . .
F1 F 0.40679(9) 0.1705(2) 0.4327(2) 0.0748(5) Uani 1 1 d . . . . .
F2 F 0.32280(8) 0.2816(3) 0.32804(17) 0.0807(6) Uani 1 1 d . . . . .
F3 F 0.40312(9) 0.4135(2) 0.42211(18) 0.0692(5) Uani 1 1 d . . . . .
C1 C 0.37039(10) 0.5986(3) 0.7553(2) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.38969(11) 0.7691(3) 0.7711(3) 0.0416(5) Uani 1 1 d . . . . .
H2A H 0.433130 0.775802 0.826135 0.050 Uiso 1 1 calc R U . . .
C3 C 0.34917(12) 0.8382(3) 0.8694(3) 0.0504(6) Uani 1 1 d . . . . .
H3A H 0.307262 0.854178 0.810582 0.060 Uiso 1 1 calc R U . . .
H3B H 0.365884 0.935126 0.912423 0.060 Uiso 1 1 calc R U . . .
C4 C 0.35044(12) 0.7189(3) 0.9952(3) 0.0513(6) Uani 1 1 d . . . . .
C5 C 0.34597(11) 0.5669(3) 0.9037(3) 0.0415(5) Uani 1 1 d . . . . .
H5A H 0.301775 0.542711 0.870537 0.050 Uiso 1 1 calc R U . . .
C6 C 0.37688(13) 0.4280(3) 0.9916(3) 0.0504(6) Uani 1 1 d . . . . .
H6A H 0.355293 0.402470 1.071409 0.060 Uiso 1 1 calc R U . . .
H6B H 0.419334 0.453551 1.040206 0.060 Uiso 1 1 calc R U . . .
C7 C 0.37674(11) 0.2894(3) 0.8889(3) 0.0458(5) Uani 1 1 d . . . . .
H7A H 0.334507 0.252787 0.855863 0.055 Uiso 1 1 calc R U . . .
H7B H 0.400882 0.208673 0.948096 0.055 Uiso 1 1 calc R U . . .
C8 C 0.40344(9) 0.3216(3) 0.7449(2) 0.0370(5) Uani 1 1 d . . . . .
C9 C 0.35010(10) 0.2909(3) 0.5998(2) 0.0398(5) Uani 1 1 d . . . . .
C10 C 0.29810(10) 0.4073(3) 0.5927(3) 0.0444(6) Uani 1 1 d . . . . .
H10A H 0.276079 0.382782 0.671933 0.053 Uiso 1 1 calc R U . . .
H10B H 0.269030 0.396846 0.495038 0.053 Uiso 1 1 calc R U . . .
C11 C 0.31928(11) 0.5738(3) 0.6121(3) 0.0423(6) Uani 1 1 d . . . . .
H11A H 0.284064 0.637910 0.617836 0.051 Uiso 1 1 calc R U . . .
H11B H 0.334355 0.605101 0.523121 0.051 Uiso 1 1 calc R U . . .
C12 C 0.42391(10) 0.4896(3) 0.7491(3) 0.0383(5) Uani 1 1 d . . . . .
H12A H 0.457230 0.506194 0.838036 0.046 Uiso 1 1 calc R U . . .
H12B H 0.439734 0.511820 0.658861 0.046 Uiso 1 1 calc R U . . .
C13 C 0.29524(16) 0.7380(4) 1.0709(4) 0.0812(10) Uani 1 1 d . . . . .
H13A H 0.298832 0.833450 1.124958 0.122 Uiso 1 1 calc R U . . .
H13B H 0.294872 0.655503 1.141338 0.122 Uiso 1 1 calc R U . . .
H13C H 0.257412 0.736917 0.993979 0.122 Uiso 1 1 calc R U . . .
C14 C 0.41057(15) 0.7340(4) 1.1175(3) 0.0691(8) Uani 1 1 d . . . . .
H14A H 0.413551 0.835470 1.159272 0.104 Uiso 1 1 calc R U . . .
H14B H 0.445372 0.714890 1.072371 0.104 Uiso 1 1 calc R U . . .
H14C H 0.410483 0.661128 1.197444 0.104 Uiso 1 1 calc R U . . .
C15 C 0.46015(11) 0.2197(3) 0.7504(3) 0.0538(7) Uani 1 1 d . . . . .
H15A H 0.478982 0.245090 0.666954 0.081 Uiso 1 1 calc R U . . .
H15B H 0.447539 0.114436 0.742544 0.081 Uiso 1 1 calc R U . . .
H15C H 0.489505 0.235621 0.845340 0.081 Uiso 1 1 calc R U . . .
C16 C 0.42911(16) 0.8263(3) 0.5499(3) 0.0702(9) Uani 1 1 d . . . . .
H16A H 0.423865 0.894917 0.464478 0.105 Uiso 1 1 calc R U . . .
H16B H 0.426155 0.722671 0.513703 0.105 Uiso 1 1 calc R U . . .
H16C H 0.469073 0.842519 0.616007 0.105 Uiso 1 1 calc R U . . .
C17 C 0.37080(12) 0.2902(3) 0.4471(3) 0.0510(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.429(3) . ?
O1 C16 1.426(3) . ?
O2 C9 1.417(3) . ?
O2 H1 0.79(3) . ?
F1 C17 1.339(3) . ?
F2 C17 1.332(3) . ?
F3 C17 1.339(3) . ?
C1 C12 1.530(3) . ?
C1 C2 1.549(3) . ?
C1 C11 1.528(3) . ?
C1 C5 1.568(3) . ?
C2 C3 1.515(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.533(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C14 1.531(4) . ?
C4 C13 1.532(4) . ?
C4 C5 1.554(4) . ?
C5 C6 1.526(4) . ?
C5 H5A 0.9800 . ?
C6 C7 1.522(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.560(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C15 1.530(3) . ?
C8 C12 1.536(3) . ?
C8 C9 1.575(3) . ?
C9 C10 1.526(3) . ?
C9 C17 1.537(3) . ?
C10 C11 1.529(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C16 113.7(2) . . ?
C9 O2 H1 110(2) . . ?
C12 C1 C2 113.79(18) . . ?
C12 C1 C11 108.40(18) . . ?
C2 C1 C11 110.56(19) . . ?
C12 C1 C5 109.57(18) . . ?
C2 C1 C5 103.42(18) . . ?
C11 C1 C5 111.06(17) . . ?
O1 C2 C3 109.11(19) . . ?
O1 C2 C1 116.35(19) . . ?
C3 C2 C1 104.55(19) . . ?
O1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C2 C3 C4 103.9(2) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C14 109.9(2) . . ?
C3 C4 C13 111.5(2) . . ?
C14 C4 C13 108.9(2) . . ?
C3 C4 C5 101.81(19) . . ?
C14 C4 C5 113.3(2) . . ?
C13 C4 C5 111.3(2) . . ?
C6 C5 C4 116.1(2) . . ?
C6 C5 C1 112.38(19) . . ?
C4 C5 C1 107.7(2) . . ?
C6 C5 H5A 106.7 . . ?
C4 C5 H5A 106.7 . . ?
C1 C5 H5A 106.7 . . ?
C5 C6 C7 112.36(19) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 114.0(2) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C15 C8 C12 108.75(18) . . ?
C15 C8 C7 108.99(19) . . ?
C12 C8 C7 108.38(19) . . ?
C15 C8 C9 112.76(19) . . ?
C12 C8 C9 110.26(17) . . ?
C7 C8 C9 107.61(17) . . ?
O2 C9 C10 105.38(18) . . ?
O2 C9 C17 104.46(18) . . ?
C10 C9 C17 109.6(2) . . ?
O2 C9 C8 112.05(17) . . ?
C10 C9 C8 109.93(18) . . ?
C17 C9 C8 114.90(18) . . ?
C9 C10 C11 114.94(19) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C1 112.46(19) . . ?
C10 C11 H11A 109.1 . . ?
C1 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C1 C12 C8 111.78(17) . . ?
C1 C12 H12A 109.3 . . ?
C8 C12 H12A 109.3 . . ?
C1 C12 H12B 109.3 . . ?
C8 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F2 C17 F1 105.3(2) . . ?
F2 C17 F3 105.8(2) . . ?
F1 C17 F3 105.2(2) . . ?
F2 C17 C9 111.9(2) . . ?
F1 C17 C9 112.9(2) . . ?
F3 C17 C9 114.9(2) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_W-5092
_database_code_depnum_ccdc_archive 'CCDC 2169285'
loop_
_audit_author_name
_audit_author_address
'Roman Rumyantcev'
;IOMC RAS
Russia
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H23 F3 O2'
_chemical_formula_weight         292.33

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

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

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

_cell_length_a                   9.4232(3)
_cell_length_b                   10.9758(4)
_cell_length_c                   15.1715(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1569.14(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2393
_cell_measurement_theta_min      3.9040
_cell_measurement_theta_max      24.8790

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   sphere
_exptl_crystal_size_rad          0.193
_exptl_absorpt_correction_T_min  0.96899
_exptl_absorpt_correction_T_max  0.96899
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.895
_oxdiff_exptl_absorpt_empirical_full_max 1.130
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur EOS'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13401
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.150
_diffrn_reflns_theta_max         28.696
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4055
_reflns_number_gt                2640
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    SHELXT-2014/5
_computing_structure_refinement  Â
_computing_molecular_graphics    SHELXTL
_computing_publication_material  Â
_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+0.2003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 844 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4055
_refine_ls_number_parameters     211
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1192(3) 0.2976(2) 0.64250(19) 0.0783(7) Uani 1 1 d . . . . .
O2 O -0.1036(3) -0.0378(2) 0.83217(18) 0.0723(7) Uani 1 1 d . . . . .
H1 H -0.026(4) -0.072(3) 0.857(3) 0.074(11) Uiso 1 1 d . . . . .
F1 F -0.0593(8) 0.0930(10) 0.9937(4) 0.0941(15) Uani 0.478(17) 1 d D U P A 1
F2 F -0.2760(6) 0.0986(11) 0.9340(9) 0.1105(19) Uani 0.478(17) 1 d D U P A 1
F3 F -0.1378(12) 0.2555(4) 0.9241(7) 0.0947(16) Uani 0.478(17) 1 d D U P A 1
F1' F -0.172(5) 0.2474(19) 0.900(3) 0.0941(15) Uani 0.053(5) 1 d D U P A 2
F2' F -0.006(2) 0.142(4) 0.965(3) 0.1105(19) Uani 0.053(5) 1 d D U P A 2
F3' F -0.226(4) 0.104(4) 0.994(2) 0.0947(16) Uani 0.053(5) 1 d D U P A 2
F1" F -0.0942(11) 0.2459(5) 0.9520(6) 0.0941(15) Uani 0.468(17) 1 d D U P A 3
F2" F -0.2713(7) 0.1153(12) 0.9550(9) 0.1105(19) Uani 0.468(17) 1 d D U P A 3
F3" F -0.0578(8) 0.0585(9) 0.9822(5) 0.0947(16) Uani 0.468(17) 1 d D U P A 3
C1 C 0.1514(3) 0.0800(3) 0.73922(18) 0.0522(7) Uani 1 1 d . . . . .
H1A H 0.134888 -0.008120 0.740499 0.063 Uiso 1 1 calc R U . . .
C2 C 0.1710(4) 0.1184(3) 0.6437(2) 0.0668(9) Uani 1 1 d . . . . .
H2A H 0.158662 0.206067 0.640913 0.080 Uiso 1 1 calc R U . . .
H2B H 0.268596 0.101408 0.627603 0.080 Uiso 1 1 calc R U . . .
C3 C 0.0763(5) 0.0621(3) 0.5738(3) 0.0903(13) Uani 1 1 d . . . . .
H3A H 0.035140 -0.012080 0.597347 0.108 Uiso 1 1 calc R U . . .
H3B H 0.134494 0.039702 0.523628 0.108 Uiso 1 1 calc R U . . .
C4 C -0.0442(5) 0.1453(3) 0.5417(3) 0.0849(12) Uani 1 1 d . . . . .
H4A H -0.110721 0.095545 0.507481 0.102 Uiso 1 1 calc R U . . .
C5 C -0.1207(4) 0.1916(3) 0.6214(3) 0.0684(9) Uani 1 1 d . . . . .
C6 C -0.2010(4) 0.1006(4) 0.6759(3) 0.0898(13) Uani 1 1 d . . . . .
H6A H -0.294581 0.090036 0.650352 0.108 Uiso 1 1 calc R U . . .
H6B H -0.152502 0.022859 0.672450 0.108 Uiso 1 1 calc R U . . .
C7 C -0.2178(4) 0.1338(4) 0.7703(3) 0.0914(14) Uani 1 1 d . . . . .
H7A H -0.306636 0.099867 0.791403 0.110 Uiso 1 1 calc R U . . .
H7B H -0.224967 0.221744 0.774625 0.110 Uiso 1 1 calc R U . . .
C8 C -0.0979(3) 0.0907(3) 0.8318(2) 0.0641(8) Uani 1 1 d . . . . .
C9 C 0.0522(3) 0.1405(3) 0.8090(2) 0.0548(7) Uani 1 1 d . . . . .
H9A H 0.045248 0.227967 0.796619 0.066 Uiso 1 1 calc R U . . .
C10 C 0.1716(4) 0.1190(4) 0.8759(2) 0.0758(10) Uani 1 1 d . . . . .
H10A H 0.188307 0.187789 0.914687 0.091 Uiso 1 1 calc R U . . .
H10B H 0.160705 0.044354 0.909510 0.091 Uiso 1 1 calc R U . . .
C11 C 0.2791(3) 0.1089(3) 0.8008(2) 0.0688(9) Uani 1 1 d . . . . .
C12 C 0.3892(4) 0.0085(4) 0.8071(3) 0.0999(15) Uani 1 1 d . . . . .
H12A H 0.342475 -0.068278 0.815742 0.150 Uiso 1 1 calc R U . . .
H12B H 0.451239 0.024445 0.855912 0.150 Uiso 1 1 calc R U . . .
H12C H 0.443468 0.005868 0.753573 0.150 Uiso 1 1 calc R U . . .
C13 C 0.3494(4) 0.2311(4) 0.7813(3) 0.0908(12) Uani 1 1 d . . . . .
H13A H 0.407145 0.254731 0.830545 0.136 Uiso 1 1 calc R U . . .
H13B H 0.277705 0.291641 0.771380 0.136 Uiso 1 1 calc R U . . .
H13C H 0.407759 0.223744 0.729676 0.136 Uiso 1 1 calc R U . . .
C14 C 0.0090(5) 0.2474(5) 0.4827(3) 0.0976(14) Uani 1 1 d . . . . .
H14A H -0.068183 0.301081 0.468650 0.146 Uiso 1 1 calc R U . . .
H14B H 0.047035 0.213495 0.429397 0.146 Uiso 1 1 calc R U . . .
H14C H 0.081832 0.292228 0.512858 0.146 Uiso 1 1 calc R U . . .
C15 C -0.1365(4) 0.1321(3) 0.9259(3) 0.0985(16) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.206(4) . ?
O2 C8 1.411(4) . ?
F1 C15 1.331(6) . ?
F2 C15 1.370(6) . ?
F3 C15 1.355(5) . ?
F1' C15 1.367(7) . ?
F2' C15 1.369(8) . ?
F3' C15 1.363(7) . ?
F1" C15 1.371(5) . ?
F2" C15 1.358(6) . ?
F3" C15 1.390(6) . ?
C1 C2 1.520(4) . ?
C1 C11 1.556(4) . ?
C1 C9 1.561(4) . ?
C2 C3 1.518(5) . ?
C3 C4 1.536(5) . ?
C4 C5 1.496(6) . ?
C4 C14 1.520(7) . ?
C5 C6 1.502(5) . ?
C6 C7 1.486(6) . ?
C7 C8 1.540(6) . ?
C8 C15 1.542(6) . ?
C8 C9 1.555(4) . ?
C9 C10 1.534(5) . ?
C10 C11 1.530(5) . ?
C11 C12 1.516(5) . ?
C11 C13 1.524(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 114.9(2) . . ?
C2 C1 C9 127.0(3) . . ?
C11 C1 C9 88.3(2) . . ?
C3 C2 C1 118.8(3) . . ?
C2 C3 C4 114.5(3) . . ?
C5 C4 C14 112.6(3) . . ?
C5 C4 C3 107.6(3) . . ?
C14 C4 C3 112.4(4) . . ?
O1 C5 C4 122.5(3) . . ?
O1 C5 C6 120.1(4) . . ?
C4 C5 C6 117.5(3) . . ?
C7 C6 C5 115.0(3) . . ?
C6 C7 C8 115.5(3) . . ?
O2 C8 C7 106.3(3) . . ?
O2 C8 C15 106.3(3) . . ?
C7 C8 C15 107.3(3) . . ?
O2 C8 C9 112.8(3) . . ?
C7 C8 C9 115.2(3) . . ?
C15 C8 C9 108.5(3) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 C1 86.8(2) . . ?
C8 C9 C1 123.1(3) . . ?
C11 C10 C9 90.2(2) . . ?
C12 C11 C13 110.7(3) . . ?
C12 C11 C10 117.3(3) . . ?
C13 C11 C10 111.7(3) . . ?
C12 C11 C1 114.8(3) . . ?
C13 C11 C1 113.5(3) . . ?
C10 C11 C1 87.1(2) . . ?
F1 C15 F3 110.0(5) . . ?
F3' C15 F1' 105.7(11) . . ?
F3' C15 F2' 104.4(11) . . ?
F1' C15 F2' 105.5(11) . . ?
F1 C15 F2 111.6(6) . . ?
F3 C15 F2 105.1(6) . . ?
F2" C15 F1" 107.6(6) . . ?
F2" C15 F3" 102.7(6) . . ?
F1" C15 F3" 101.4(5) . . ?
F1 C15 C8 119.5(5) . . ?
F3 C15 C8 106.1(4) . . ?
F2" C15 C8 118.9(7) . . ?
F3' C15 C8 141.0(18) . . ?
F1' C15 C8 94.0(19) . . ?
F2' C15 C8 102.1(18) . . ?
F2 C15 C8 103.3(6) . . ?
F1" C15 C8 117.9(4) . . ?
F3" C15 C8 105.8(4) . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_W-814
_database_code_depnum_ccdc_archive 'CCDC 2169286'
loop_
_audit_author_name
_audit_author_address
'Roman Rumyantcev'
;IOMC RAS
Russia
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H23 F3 O2'
_chemical_formula_weight         292.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   28.9014(11)
_cell_length_b                   6.6072(3)
_cell_length_c                   20.4393(8)
_cell_angle_alpha                90
_cell_angle_beta                 129.2716(11)
_cell_angle_gamma                90
_cell_volume                     3021.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      25.29

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Quest (CMOS)'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17371
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_full        25.023
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5290
_reflns_number_gt                4354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

_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       APEX3
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT-2014/5
_computing_structure_refinement  SHELXL-2018/3
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0441P)²+1.4107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0101(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5290
_refine_ls_number_parameters     381
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.030
_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
O1A O 0.51277(11) 0.5030(6) 0.60640(16) 0.0822(10) Uani 1 1 d . . . . .
H1 H 0.482(2) 0.512(9) 0.561(3) 0.099 Uiso 1 1 d . U . . .
O2A O 0.60280(8) 0.4646(3) 0.78714(12) 0.0420(5) Uani 1 1 d . . . . .
F1A F 0.70388(8) 0.4574(4) 1.01098(11) 0.0666(6) Uani 1 1 d . . . . .
F2A F 0.67235(9) 0.7128(3) 0.92840(14) 0.0699(6) Uani 1 1 d . . . . .
F3A F 0.72088(8) 0.4787(4) 0.92392(13) 0.0715(6) Uani 1 1 d . . . . .
C1A C 0.53080(13) 0.6247(6) 0.81776(18) 0.0542(9) Uani 1 1 d D . . . .
H1AA H 0.557970 0.735259 0.830356 0.065 Uiso 0.724(5) 1 calc R U P A 1
H1AB H 0.548315 0.738826 0.809551 0.065 Uiso 0.276(5) 1 calc R U P A 2
C2A C 0.4824(2) 0.6271(7) 0.7195(2) 0.0520(13) Uani 0.724(5) 1 d D . P A 1
H2AA H 0.445616 0.679925 0.705018 0.062 Uiso 0.724(5) 1 calc R U P A 1
H2AB H 0.495243 0.720544 0.697219 0.062 Uiso 0.724(5) 1 calc R U P A 1
C3A C 0.46883(17) 0.4253(8) 0.6755(3) 0.0498(13) Uani 0.724(5) 1 d D . P A 1
H3AA H 0.427728 0.429049 0.623694 0.060 Uiso 0.724(5) 1 calc R U P A 1
H3AB H 0.471193 0.322017 0.711254 0.060 Uiso 0.724(5) 1 calc R U P A 1
C2' C 0.4735(4) 0.526(2) 0.7368(5) 0.0520(13) Uani 0.276(5) 1 d D . P A 2
H2'A H 0.469470 0.387845 0.748630 0.062 Uiso 0.276(5) 1 calc R U P A 2
H2'B H 0.438301 0.601243 0.718737 0.062 Uiso 0.276(5) 1 calc R U P A 2
C3' C 0.4792(6) 0.5290(16) 0.6678(7) 0.0498(13) Uani 0.276(5) 1 d D . P A 2
H3'A H 0.501125 0.651139 0.676618 0.060 Uiso 0.276(5) 1 calc R U P A 2
H3'B H 0.439092 0.547172 0.614911 0.060 Uiso 0.276(5) 1 calc R U P A 2
C4A C 0.50773(13) 0.3568(5) 0.65296(18) 0.0454(8) Uani 1 1 d D . . . .
C5A C 0.57229(14) 0.3009(5) 0.72776(19) 0.0457(7) Uani 1 1 d . . . . .
H5AA H 0.593281 0.273822 0.705387 0.055 Uiso 1 1 calc R U . . .
C6A C 0.58048(16) 0.1150(5) 0.7792(2) 0.0551(8) Uani 1 1 d . . . . .
H6AA H 0.544823 0.089316 0.772993 0.066 Uiso 1 1 calc R U . . .
H6AB H 0.589805 -0.004492 0.761959 0.066 Uiso 1 1 calc R U . . .
C7A C 0.63280(15) 0.1743(5) 0.8697(2) 0.0502(8) Uani 1 1 d . . . . .
H7AA H 0.670836 0.146739 0.882782 0.060 Uiso 1 1 calc R U . . .
H7AB H 0.631274 0.104844 0.910127 0.060 Uiso 1 1 calc R U . . .
C8A C 0.62220(12) 0.4001(4) 0.86797(18) 0.0389(7) Uani 1 1 d . . . . .
C9A C 0.57226(13) 0.4483(5) 0.87181(19) 0.0448(7) Uani 1 1 d . . . . .
H9AA H 0.547412 0.326792 0.853642 0.054 Uiso 1 1 calc R U . . .
C10A C 0.57884(16) 0.5403(6) 0.9466(2) 0.0592(9) Uani 1 1 d . . . . .
H10A H 0.613240 0.628344 0.982244 0.071 Uiso 1 1 calc R U . . .
H10B H 0.577123 0.441392 0.980116 0.071 Uiso 1 1 calc R U . . .
C11A C 0.51949(14) 0.6542(6) 0.8821(2) 0.0588(10) Uani 1 1 d . . . . .
C12A C 0.4657(2) 0.5393(9) 0.8589(4) 0.1088(19) Uani 1 1 d . . . . .
H12A H 0.468415 0.524949 0.907924 0.163 Uiso 1 1 calc R U . . .
H12B H 0.464600 0.407733 0.837955 0.163 Uiso 1 1 calc R U . . .
H12C H 0.429962 0.612109 0.815912 0.163 Uiso 1 1 calc R U . . .
C13A C 0.51677(19) 0.8707(7) 0.9029(3) 0.0769(12) Uani 1 1 d . . . . .
H13A H 0.513549 0.873214 0.946881 0.115 Uiso 1 1 calc R U . . .
H13B H 0.482583 0.936213 0.853445 0.115 Uiso 1 1 calc R U . . .
H13C H 0.552443 0.940392 0.921706 0.115 Uiso 1 1 calc R U . . .
C14A C 0.4756(2) 0.1738(8) 0.5973(3) 0.107(2) Uani 1 1 d . . . . .
H14A H 0.437165 0.213805 0.546446 0.161 Uiso 1 1 calc R U . . .
H14B H 0.470425 0.075625 0.626831 0.161 Uiso 1 1 calc R U . . .
H14C H 0.498713 0.115653 0.583183 0.161 Uiso 1 1 calc R U . . .
C15A C 0.67935(13) 0.5129(6) 0.93233(19) 0.0488(8) Uani 1 1 d . . . . .
O1B O 0.40857(10) 0.5378(5) 0.43485(15) 0.0681(8) Uani 1 1 d . . . . .
H2 H 0.426(2) 0.512(7) 0.420(3) 0.082 Uiso 1 1 d . U . . .
O2B O 0.28995(9) 0.4659(4) 0.27770(13) 0.0518(6) Uani 1 1 d . . . . .
F1B F 0.19572(13) 0.1963(4) 0.2211(2) 0.1026(9) Uani 1 1 d . . . . .
F2B F 0.21265(13) 0.2511(5) 0.13490(18) 0.1081(11) Uani 1 1 d . . . . .
F3B F 0.13598(10) 0.3837(5) 0.11238(17) 0.1137(11) Uani 1 1 d . . . . .
C1B C 0.24331(12) 0.5322(6) 0.36132(19) 0.0518(8) Uani 1 1 d D . . . .
H1BA H 0.240898 0.384278 0.356676 0.062 Uiso 1 1 calc R U . . .
C2B C 0.30824(13) 0.5879(7) 0.43620(19) 0.0588(10) Uani 1 1 d D . . . .
H2BA H 0.309493 0.626913 0.483054 0.071 Uiso 1 1 calc R U . . .
H2BB H 0.332317 0.466610 0.453257 0.071 Uiso 1 1 calc R U . . .
C3B C 0.33793(15) 0.7543(6) 0.4235(2) 0.0605(10) Uani 1 1 d D . . . .
H3BA H 0.368026 0.816216 0.478077 0.073 Uiso 1 1 calc R U . . .
H3BB H 0.307956 0.856810 0.387897 0.073 Uiso 1 1 calc R U . . .
C4B C 0.36798(14) 0.7009(6) 0.3847(2) 0.0541(9) Uani 1 1 d D . . . .
C5B C 0.32689(14) 0.6343(6) 0.2924(2) 0.0522(8) Uani 1 1 d . . . . .
H5BA H 0.352591 0.588211 0.279546 0.063 Uiso 1 1 calc R U . . .
C6B C 0.28508(17) 0.7944(7) 0.2268(2) 0.0659(10) Uani 1 1 d . . . . .
H6BA H 0.280611 0.907079 0.252826 0.079 Uiso 1 1 calc R U . . .
H6BB H 0.300047 0.844891 0.198747 0.079 Uiso 1 1 calc R U . . .
C7B C 0.22615(17) 0.6842(7) 0.1649(2) 0.0698(12) Uani 1 1 d . . . . .
H7BA H 0.192414 0.774760 0.140322 0.084 Uiso 1 1 calc R U . . .
H7BB H 0.223776 0.621032 0.119981 0.084 Uiso 1 1 calc R U . . .
C8B C 0.22885(14) 0.5279(6) 0.22124(19) 0.0542(9) Uani 1 1 d . . . . .
C9B C 0.21329(13) 0.6176(6) 0.27342(18) 0.0480(8) Uani 1 1 d . . . . .
H9BB H 0.223502 0.761717 0.280618 0.058 Uiso 1 1 calc R U . . .
C10B C 0.15287(14) 0.6016(7) 0.2554(2) 0.0629(10) Uani 1 1 d . . . . .
H10C H 0.126721 0.716827 0.225172 0.075 Uiso 1 1 calc R U . . .
H10D H 0.131920 0.475247 0.229085 0.075 Uiso 1 1 calc R U . . .
C11B C 0.18762(15) 0.6083(7) 0.3512(2) 0.0639(10) Uani 1 1 d . . . . .
C12B C 0.19386(18) 0.8218(9) 0.3824(3) 0.0889(15) Uani 1 1 d . . . . .
H12D H 0.155291 0.872175 0.360424 0.133 Uiso 1 1 calc R U . . .
H12E H 0.210297 0.906644 0.363474 0.133 Uiso 1 1 calc R U . . .
H12F H 0.219960 0.822205 0.443016 0.133 Uiso 1 1 calc R U . . .
C13B C 0.1648(2) 0.4708(10) 0.3843(3) 0.1083(19) Uani 1 1 d . . . . .
H13D H 0.124860 0.510081 0.360357 0.162 Uiso 1 1 calc R U . . .
H13E H 0.190292 0.481567 0.444759 0.162 Uiso 1 1 calc R U . . .
H13F H 0.164582 0.333463 0.368846 0.162 Uiso 1 1 calc R U . . .
C14B C 0.40427(19) 0.8821(9) 0.3936(3) 0.0886(14) Uani 1 1 d . . . . .
H14D H 0.420842 0.853043 0.366163 0.133 Uiso 1 1 calc R U . . .
H14E H 0.436024 0.908775 0.452428 0.133 Uiso 1 1 calc R U . . .
H14F H 0.378776 0.998636 0.367845 0.133 Uiso 1 1 calc R U . . .
C15B C 0.19377(19) 0.3395(8) 0.1731(3) 0.0807(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C4A 1.427(4) . ?
O1A H1 0.79(5) . ?
O2A C8A 1.433(3) . ?
O2A C5A 1.437(4) . ?
F1A C15A 1.334(4) . ?
F2A C15A 1.331(4) . ?
F3A C15A 1.335(4) . ?
C1A C9A 1.530(5) . ?
C1A C2A 1.560(4) . ?
C1A C2' 1.561(6) . ?
C1A C11A 1.556(5) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C2A C3A 1.514(5) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C3A C4A 1.529(4) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C2' C3' 1.520(7) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C3' C4A 1.544(6) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C4A C14A 1.511(6) . ?
C4A C5A 1.531(4) . ?
C5A C6A 1.535(5) . ?
C5A H5AA 0.9800 . ?
C6A C7A 1.523(5) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7A C8A 1.519(4) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A C15A 1.504(4) . ?
C8A C9A 1.528(4) . ?
C9A C10A 1.541(5) . ?
C9A H9AA 0.9800 . ?
C10A C11A 1.544(5) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C13A 1.508(6) . ?
C11A C12A 1.511(6) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
O1B C4B 1.437(5) . ?
O1B H2 0.76(4) . ?
O2B C8B 1.428(4) . ?
O2B C5B 1.436(4) . ?
F1B C15B 1.337(6) . ?
F2B C15B 1.338(5) . ?
F3B C15B 1.338(5) . ?
C1B C9B 1.525(4) . ?
C1B C2B 1.537(4) . ?
C1B C11B 1.570(4) . ?
C1B H1BA 0.9800 . ?
C2B C3B 1.515(5) . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C3B C4B 1.541(4) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B C14B 1.525(6) . ?
C4B C5B 1.526(5) . ?
C5B C6B 1.525(5) . ?
C5B H5BA 0.9800 . ?
C6B C7B 1.518(6) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7B C8B 1.512(5) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B C15B 1.511(6) . ?
C8B C9B 1.516(4) . ?
C9B C10B 1.543(4) . ?
C9B H9BB 0.9800 . ?
C10B C11B 1.536(5) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B C12B 1.510(7) . ?
C11B C13B 1.512(6) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?

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
C4A O1A H1 109(4) . . ?
C8A O2A C5A 109.4(2) . . ?
C9A C1A C2A 126.3(3) . . ?
C9A C1A C2' 105.5(6) . . ?
C9A C1A C11A 88.4(3) . . ?
C2A C1A C11A 126.2(3) . . ?
C2' C1A C11A 107.4(4) . . ?
C9A C1A H1AA 104.3 . . ?
C2A C1A H1AA 104.3 . . ?
C11A C1A H1AA 104.3 . . ?
C9A C1A H1AB 117.2 . . ?
C2' C1A H1AB 117.2 . . ?
C11A C1A H1AB 117.2 . . ?
C3A C2A C1A 116.1(4) . . ?
C3A C2A H2AA 108.3 . . ?
C1A C2A H2AA 108.3 . . ?
C3A C2A H2AB 108.3 . . ?
C1A C2A H2AB 108.3 . . ?
H2AA C2A H2AB 107.4 . . ?
C2A C3A C4A 118.4(4) . . ?
C2A C3A H3AA 107.7 . . ?
C4A C3A H3AA 107.7 . . ?
C2A C3A H3AB 107.7 . . ?
C4A C3A H3AB 107.7 . . ?
H3AA C3A H3AB 107.1 . . ?
C3' C2' C1A 108.2(8) . . ?
C3' C2' H2'A 110.1 . . ?
C1A C2' H2'A 110.1 . . ?
C3' C2' H2'B 110.1 . . ?
C1A C2' H2'B 110.1 . . ?
H2'A C2' H2'B 108.4 . . ?
C2' C3' C4A 124.0(9) . . ?
C2' C3' H3'A 106.3 . . ?
C4A C3' H3'A 106.3 . . ?
C2' C3' H3'B 106.3 . . ?
C4A C3' H3'B 106.3 . . ?
H3'A C3' H3'B 106.4 . . ?
O1A C4A C14A 108.3(3) . . ?
O1A C4A C3A 114.0(3) . . ?
C14A C4A C3A 104.2(4) . . ?
O1A C4A C5A 104.8(2) . . ?
C14A C4A C5A 109.8(3) . . ?
C3A C4A C5A 115.7(3) . . ?
O1A C4A C3' 85.7(5) . . ?
C14A C4A C3' 126.0(6) . . ?
C5A C4A C3' 116.5(5) . . ?
O2A C5A C6A 106.1(2) . . ?
O2A C5A C4A 111.7(3) . . ?
C6A C5A C4A 116.1(3) . . ?
O2A C5A H5AA 107.5 . . ?
C6A C5A H5AA 107.5 . . ?
C4A C5A H5AA 107.5 . . ?
C7A C6A C5A 103.3(3) . . ?
C7A C6A H6AA 111.1 . . ?
C5A C6A H6AA 111.1 . . ?
C7A C6A H6AB 111.1 . . ?
C5A C6A H6AB 111.1 . . ?
H6AA C6A H6AB 109.1 . . ?
C6A C7A C8A 101.2(3) . . ?
C6A C7A H7AA 111.5 . . ?
C8A C7A H7AA 111.5 . . ?
C6A C7A H7AB 111.5 . . ?
C8A C7A H7AB 111.5 . . ?
H7AA C7A H7AB 109.4 . . ?
O2A C8A C15A 105.8(2) . . ?
O2A C8A C7A 104.2(2) . . ?
C15A C8A C7A 111.9(3) . . ?
O2A C8A C9A 107.7(2) . . ?
C15A C8A C9A 113.7(3) . . ?
C7A C8A C9A 112.7(3) . . ?
C1A C9A C8A 117.1(3) . . ?
C1A C9A C10A 87.9(2) . . ?
C8A C9A C10A 127.3(3) . . ?
C1A C9A H9AA 107.4 . . ?
C8A C9A H9AA 107.4 . . ?
C10A C9A H9AA 107.4 . . ?
C9A C10A C11A 88.4(2) . . ?
C9A C10A H10A 113.9 . . ?
C11A C10A H10A 113.9 . . ?
C9A C10A H10B 113.9 . . ?
C11A C10A H10B 113.9 . . ?
H10A C10A H10B 111.1 . . ?
C13A C11A C12A 109.8(3) . . ?
C13A C11A C10A 116.7(3) . . ?
C12A C11A C10A 112.9(4) . . ?
C13A C11A C1A 115.7(4) . . ?
C12A C11A C1A 113.3(3) . . ?
C10A C11A C1A 86.9(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C4A C14A H14A 109.5 . . ?
C4A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C4A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
F2A C15A F1A 106.9(3) . . ?
F2A C15A F3A 105.9(3) . . ?
F1A C15A F3A 105.9(2) . . ?
F2A C15A C8A 113.5(3) . . ?
F1A C15A C8A 111.7(3) . . ?
F3A C15A C8A 112.5(3) . . ?
C4B O1B H2 110(4) . . ?
C8B O2B C5B 108.8(3) . . ?
C9B C1B C2B 120.7(3) . . ?
C9B C1B C11B 87.4(2) . . ?
C2B C1B C11B 123.9(3) . . ?
C9B C1B H1BA 107.6 . . ?
C2B C1B H1BA 107.6 . . ?
C11B C1B H1BA 107.6 . . ?
C3B C2B C1B 118.0(3) . . ?
C3B C2B H2BA 107.8 . . ?
C1B C2B H2BA 107.8 . . ?
C3B C2B H2BB 107.8 . . ?
C1B C2B H2BB 107.8 . . ?
H2BA C2B H2BB 107.1 . . ?
C2B C3B C4B 119.1(3) . . ?
C2B C3B H3BA 107.5 . . ?
C4B C3B H3BA 107.5 . . ?
C2B C3B H3BB 107.5 . . ?
C4B C3B H3BB 107.5 . . ?
H3BA C3B H3BB 107.0 . . ?
O1B C4B C14B 108.3(3) . . ?
O1B C4B C5B 108.1(3) . . ?
C14B C4B C5B 108.2(3) . . ?
O1B C4B C3B 106.1(3) . . ?
C14B C4B C3B 109.1(3) . . ?
C5B C4B C3B 116.8(3) . . ?
O2B C5B C6B 106.4(3) . . ?
O2B C5B C4B 112.1(3) . . ?
C6B C5B C4B 116.8(3) . . ?
O2B C5B H5BA 107.0 . . ?
C6B C5B H5BA 107.0 . . ?
C4B C5B H5BA 107.0 . . ?
C7B C6B C5B 104.3(3) . . ?
C7B C6B H6BA 110.9 . . ?
C5B C6B H6BA 110.9 . . ?
C7B C6B H6BB 110.9 . . ?
C5B C6B H6BB 110.9 . . ?
H6BA C6B H6BB 108.9 . . ?
C8B C7B C6B 101.7(3) . . ?
C8B C7B H7BA 111.4 . . ?
C6B C7B H7BA 111.4 . . ?
C8B C7B H7BB 111.4 . . ?
C6B C7B H7BB 111.4 . . ?
H7BA C7B H7BB 109.3 . . ?
O2B C8B C7B 104.7(3) . . ?
O2B C8B C15B 105.5(3) . . ?
C7B C8B C15B 112.2(3) . . ?
O2B C8B C9B 108.0(2) . . ?
C7B C8B C9B 112.0(3) . . ?
C15B C8B C9B 113.8(3) . . ?
C8B C9B C1B 118.9(3) . . ?
C8B C9B C10B 126.9(3) . . ?
C1B C9B C10B 88.3(3) . . ?
C8B C9B H9BB 106.9 . . ?
C1B C9B H9BB 106.9 . . ?
C10B C9B H9BB 106.9 . . ?
C11B C10B C9B 88.0(2) . . ?
C11B C10B H10C 114.0 . . ?
C9B C10B H10C 114.0 . . ?
C11B C10B H10D 114.0 . . ?
C9B C10B H10D 114.0 . . ?
H10C C10B H10D 111.2 . . ?
C12B C11B C13B 110.0(4) . . ?
C12B C11B C10B 111.8(4) . . ?
C13B C11B C10B 115.8(4) . . ?
C12B C11B C1B 113.9(3) . . ?
C13B C11B C1B 116.8(4) . . ?
C10B C11B C1B 86.9(2) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C4B C14B H14D 109.5 . . ?
C4B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C4B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
F1B C15B F3B 106.4(4) . . ?
F1B C15B F2B 106.0(4) . . ?
F3B C15B F2B 106.5(3) . . ?
F1B C15B C8B 114.0(3) . . ?
F3B C15B C8B 110.7(4) . . ?
F2B C15B C8B 112.7(4) . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.031

