# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1503420'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-01
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H28 F4'
_chemical_formula_moiety         'C21 H28 F4'
_chemical_formula_weight         356.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P2/c
_space_group_name_Hall           '-P 2yc'
_space_group_IT_number           13
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.943(2)
_cell_length_b                   5.5757(11)
_cell_length_c                   27.176(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.791(7)
_cell_angle_gamma                90.0000
_cell_volume                     1808.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1998
_cell_measurement_theta_min      24.02
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.00
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.983

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            23264
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_theta_max         68.262
_diffrn_reflns_theta_min         3.254
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3315
_reflns_number_gt                3025
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1699
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     227
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1323P)²+0.3158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43852(8) 0.13875(14) 0.33544(4) 0.0358(3) Uani 1 1 d . . . . .
F2 F 0.65333(8) 0.13964(17) 0.36736(3) 0.0358(3) Uani 1 1 d . . . . .
F3 F 0.43928(9) 0.6803(2) 0.46102(3) 0.0488(4) Uani 1 1 d . . . . .
F4 F 0.31097(7) 0.45189(18) 0.39089(3) 0.0326(3) Uani 1 1 d . . . . .
C1 C 0.50295(13) 0.3428(2) 0.32672(5) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.5388 0.3257 0.2941 0.029 Uiso 1 1 calc R U . . .
C2 C 0.59347(12) 0.3559(2) 0.36672(5) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.6458 0.4896 0.3589 0.029 Uiso 1 1 calc R U . . .
C3 C 0.54730(13) 0.3993(3) 0.41714(5) 0.0258(4) Uani 1 1 d . . . . .
H3A H 0.6092 0.4091 0.4422 0.031 Uiso 1 1 calc R U . . .
H3B H 0.4970 0.2662 0.4262 0.031 Uiso 1 1 calc R U . . .
C4 C 0.48291(13) 0.6339(3) 0.41502(5) 0.0278(4) Uani 1 1 d . . . . .
H4 H 0.5354 0.7663 0.4065 0.033 Uiso 1 1 calc R U . . .
C5 C 0.38734(12) 0.6272(2) 0.37701(5) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.3492 0.7868 0.3760 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43050(11) 0.5689(2) 0.32605(5) 0.0186(3) Uani 1 1 d . . . . .
H6 H 0.4821 0.7034 0.3179 0.022 Uiso 1 1 calc R U . . .
C7 C 0.33780(11) 0.5732(2) 0.28620(5) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.25458(12) 0.3983(3) 0.28187(5) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.2558 0.2655 0.3038 0.028 Uiso 1 1 calc R U . . .
C9 C 0.16939(12) 0.4166(2) 0.24558(5) 0.0228(3) Uani 1 1 d . . . . .
H9 H 0.1145 0.2935 0.2429 0.027 Uiso 1 1 calc R U . . .
C10 C 0.16275(11) 0.6100(2) 0.21329(5) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.24641(11) 0.7844(3) 0.21775(5) 0.0226(3) Uani 1 1 d . . . . .
H11 H 0.2450 0.9176 0.1959 0.027 Uiso 1 1 calc R U . . .
C12 C 0.33186(11) 0.7665(2) 0.25359(5) 0.0210(3) Uani 1 1 d . . . . .
H12 H 0.3873 0.8885 0.2559 0.025 Uiso 1 1 calc R U . . .
C13 C 0.07032(11) 0.6261(2) 0.17361(5) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.0135 0.5001 0.1808 0.026 Uiso 1 1 calc R U . . .
C14 C 0.11568(12) 0.5729(3) 0.12267(5) 0.0240(3) Uani 1 1 d . . . . .
H14A H 0.1494 0.4108 0.1227 0.029 Uiso 1 1 calc R U . . .
H14B H 0.1752 0.6901 0.1153 0.029 Uiso 1 1 calc R U . . .
C15 C 0.02322(13) 0.5863(3) 0.08243(5) 0.0262(4) Uani 1 1 d . . . . .
H15A H 0.0563 0.5574 0.0500 0.031 Uiso 1 1 calc R U . . .
H15B H -0.0324 0.4583 0.0880 0.031 Uiso 1 1 calc R U . . .
C16 C -0.03631(12) 0.8296(3) 0.08148(5) 0.0220(3) Uani 1 1 d . . . . .
H16 H 0.0205 0.9556 0.0744 0.026 Uiso 1 1 calc R U . . .
C17 C -0.08203(12) 0.8803(3) 0.13229(5) 0.0249(3) Uani 1 1 d . . . . .
H17A H -0.1409 0.7614 0.1394 0.030 Uiso 1 1 calc R U . . .
H17B H -0.1169 1.0415 0.1322 0.030 Uiso 1 1 calc R U . . .
C18 C 0.01013(12) 0.8693(3) 0.17294(5) 0.0253(4) Uani 1 1 d . . . . .
H18A H 0.0653 0.9984 0.1676 0.030 Uiso 1 1 calc R U . . .
H18B H -0.0236 0.8969 0.2053 0.030 Uiso 1 1 calc R U . . .
C19 C -0.12715(12) 0.8371(3) 0.04013(5) 0.0242(3) Uani 1 1 d . . . . .
H19A H -0.0940 0.7803 0.0093 0.029 Uiso 1 1 calc R U . . .
H19B H -0.1876 0.7238 0.0484 0.029 Uiso 1 1 calc R U . . .
C20 C -0.17840(15) 1.0820(3) 0.03095(6) 0.0340(4) Uani 1 1 d . . . . .
H20A H -0.1178 1.1977 0.0244 0.041 Uiso 1 1 calc R U . . .
H20B H -0.2156 1.1351 0.0611 0.041 Uiso 1 1 calc R U . . .
C21 C -0.26365(14) 1.0872(3) -0.01213(6) 0.0362(4) Uani 1 1 d . . . . .
H21A H -0.3270 0.9827 -0.0048 0.043 Uiso 1 1 calc R U . . .
H21B H -0.2281 1.0307 -0.0420 0.043 Uiso 1 1 calc R U . . .
H21C H -0.2906 1.2517 -0.0172 0.043 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3979(17) . ?
F2 C2 1.4017(16) . ?
F3 C4 1.3934(18) . ?
F4 C5 1.3968(17) . ?
C1 C2 1.5108(19) . ?
C1 C6 1.5287(18) . ?
C1 H1 1.0000 . ?
C2 C3 1.512(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5158(19) . ?
C4 H4 1.0000 . ?
C5 C6 1.5278(19) . ?
C5 H5 1.0000 . ?
C6 C7 1.5244(17) . ?
C6 H6 1.0000 . ?
C7 C8 1.395(2) . ?
C7 C12 1.3958(19) . ?
C8 C9 1.398(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3968(19) . ?
C10 C13 1.5214(18) . ?
C11 C12 1.3921(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.531(2) . ?
C13 C18 1.5346(19) . ?
C13 H13 1.0000 . ?
C14 C15 1.5313(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5310(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5270(19) . ?
C16 C19 1.5380(18) . ?
C16 H16 1.0000 . ?
C17 C18 1.5361(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.514(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.528(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 107.62(11) . . ?
F1 C1 C6 111.03(11) . . ?
C2 C1 C6 111.14(11) . . ?
F1 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C6 C1 H1 109.0 . . ?
F2 C2 C1 108.69(11) . . ?
F2 C2 C3 109.07(11) . . ?
C1 C2 C3 112.75(12) . . ?
F2 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C2 C3 C4 107.59(12) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
F3 C4 C5 108.74(12) . . ?
F3 C4 C3 109.22(12) . . ?
C5 C4 C3 111.98(11) . . ?
F3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
F4 C5 C4 108.51(11) . . ?
F4 C5 C6 109.73(11) . . ?
C4 C5 C6 110.79(11) . . ?
F4 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C7 C6 C5 112.49(11) . . ?
C7 C6 C1 114.82(11) . . ?
C5 C6 C1 111.81(11) . . ?
C7 C6 H6 105.6 . . ?
C5 C6 H6 105.6 . . ?
C1 C6 H6 105.6 . . ?
C8 C7 C12 117.67(12) . . ?
C8 C7 C6 123.28(12) . . ?
C12 C7 C6 118.98(11) . . ?
C7 C8 C9 120.64(12) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 121.81(13) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 117.29(13) . . ?
C9 C10 C13 121.24(12) . . ?
C11 C10 C13 121.44(12) . . ?
C12 C11 C10 121.17(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 121.40(12) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C10 C13 C14 111.10(11) . . ?
C10 C13 C18 112.94(11) . . ?
C14 C13 C18 109.82(11) . . ?
C10 C13 H13 107.6 . . ?
C14 C13 H13 107.6 . . ?
C18 C13 H13 107.6 . . ?
C13 C14 C15 111.63(11) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 112.29(11) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 109.15(11) . . ?
C17 C16 C19 113.06(11) . . ?
C15 C16 C19 110.67(11) . . ?
C17 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C19 C16 H16 107.9 . . ?
C16 C17 C18 111.99(11) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C13 C18 C17 111.65(11) . . ?
C13 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C13 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C16 114.65(11) . . ?
C20 C19 H19A 108.6 . . ?
C16 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C16 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 113.56(13) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 55.14(14) . . . . ?
C6 C1 C2 F2 176.91(11) . . . . ?
F1 C1 C2 C3 -65.91(14) . . . . ?
C6 C1 C2 C3 55.85(15) . . . . ?
F2 C2 C3 C4 -179.84(12) . . . . ?
C1 C2 C3 C4 -59.00(15) . . . . ?
C2 C3 C4 F3 -179.83(12) . . . . ?
C2 C3 C4 C5 59.66(16) . . . . ?
F3 C4 C5 F4 -57.68(15) . . . . ?
C3 C4 C5 F4 63.10(15) . . . . ?
F3 C4 C5 C6 -178.21(12) . . . . ?
C3 C4 C5 C6 -57.42(16) . . . . ?
F4 C5 C6 C7 63.20(14) . . . . ?
C4 C5 C6 C7 -177.00(11) . . . . ?
F4 C5 C6 C1 -67.71(14) . . . . ?
C4 C5 C6 C1 52.08(15) . . . . ?
F1 C1 C6 C7 -61.15(14) . . . . ?
C2 C1 C6 C7 179.09(11) . . . . ?
F1 C1 C6 C5 68.56(14) . . . . ?
C2 C1 C6 C5 -51.20(15) . . . . ?
C5 C6 C7 C8 -71.56(16) . . . . ?
C1 C6 C7 C8 57.81(17) . . . . ?
C5 C6 C7 C12 105.35(14) . . . . ?
C1 C6 C7 C12 -125.27(13) . . . . ?
C12 C7 C8 C9 0.8(2) . . . . ?
C6 C7 C8 C9 177.71(12) . . . . ?
C7 C8 C9 C10 -1.3(2) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C8 C9 C10 C13 179.31(12) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C13 C10 C11 C12 -178.88(12) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C6 C7 C12 C11 -177.44(11) . . . . ?
C9 C10 C13 C14 -105.94(15) . . . . ?
C11 C10 C13 C14 71.93(16) . . . . ?
C9 C10 C13 C18 130.15(14) . . . . ?
C11 C10 C13 C18 -51.98(17) . . . . ?
C10 C13 C14 C15 179.49(11) . . . . ?
C18 C13 C14 C15 -54.84(15) . . . . ?
C13 C14 C15 C16 56.63(16) . . . . ?
C14 C15 C16 C17 -55.84(16) . . . . ?
C14 C15 C16 C19 179.12(12) . . . . ?
C15 C16 C17 C18 55.79(15) . . . . ?
C19 C16 C17 C18 179.43(11) . . . . ?
C10 C13 C18 C17 179.59(11) . . . . ?
C14 C13 C18 C17 54.98(15) . . . . ?
C16 C17 C18 C13 -56.80(16) . . . . ?
C17 C16 C19 C20 66.32(17) . . . . ?
C15 C16 C19 C20 -170.89(13) . . . . ?
C16 C19 C20 C21 176.82(13) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1503421'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-01
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H29 F3'
_chemical_formula_moiety         'C21 H29 F3'
_chemical_formula_weight         338.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   27.34(2)
_cell_length_b                   5.534(4)
_cell_length_c                   12.092(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.294(19)
_cell_angle_gamma                90.0000
_cell_volume                     1787(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    701
_cell_measurement_theta_min      24.02
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728.00
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            17873
_diffrn_reflns_av_R_equivalents  0.1377
_diffrn_reflns_theta_max         68.403
_diffrn_reflns_theta_min         3.309
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3249
_reflns_number_gt                1878
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2943
_refine_ls_wR_factor_gt          0.2512
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     218
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1122P)²+6.1854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.87716(12) 0.6903(5) 0.3765(3) 0.0387(8) Uani 1 1 d . . . . .
F2 F 0.90698(13) 0.6741(6) 0.1782(3) 0.0459(9) Uani 1 1 d . . . . .
F3 F 0.93388(11) 0.3765(6) 0.5380(2) 0.0368(8) Uani 1 1 d . . . . .
C1 C 0.86773(18) 0.4811(9) 0.3110(4) 0.0267(11) Uani 1 1 d . . . . .
H1 H 0.8342 0.4966 0.2587 0.032 Uiso 1 1 calc R U . . .
C2 C 0.90755(19) 0.4654(9) 0.2410(4) 0.0283(12) Uani 1 1 d . . . . .
H2 H 0.8994 0.3259 0.1877 0.034 Uiso 1 1 calc R U . . .
C3 C 0.95910(19) 0.4258(10) 0.3135(4) 0.0295(12) Uani 1 1 d . . . . .
H3A H 0.9686 0.5650 0.3651 0.035 Uiso 1 1 calc R U . . .
H3B H 0.9839 0.4119 0.2650 0.035 Uiso 1 1 calc R U . . .
C4 C 0.9590(2) 0.1957(11) 0.3820(5) 0.0341(13) Uani 1 1 d . . . . .
H4A H 0.9527 0.0559 0.3298 0.041 Uiso 1 1 calc R U . . .
H4B H 0.9924 0.1736 0.4321 0.041 Uiso 1 1 calc R U . . .
C5 C 0.91975(19) 0.2001(9) 0.4532(4) 0.0278(11) Uani 1 1 d . . . . .
H5 H 0.9189 0.0387 0.4899 0.033 Uiso 1 1 calc R U . . .
C6 C 0.86764(18) 0.2581(9) 0.3831(4) 0.0229(11) Uani 1 1 d . . . . .
H6 H 0.8591 0.1211 0.3285 0.028 Uiso 1 1 calc R U . . .
C7 C 0.82725(17) 0.2554(9) 0.4533(4) 0.0214(10) Uani 1 1 d . . . . .
C8 C 0.82357(18) 0.4340(9) 0.5314(4) 0.0249(11) Uani 1 1 d . . . . .
H8 H 0.8456 0.5686 0.5406 0.030 Uiso 1 1 calc R U . . .
C9 C 0.78707(18) 0.4148(9) 0.5970(4) 0.0243(11) Uani 1 1 d . . . . .
H9 H 0.7847 0.5391 0.6498 0.029 Uiso 1 1 calc R U . . .
C10 C 0.75442(18) 0.2217(9) 0.5874(4) 0.0240(11) Uani 1 1 d . . . . .
C11 C 0.75820(18) 0.0441(9) 0.5074(4) 0.0251(11) Uani 1 1 d . . . . .
H11 H 0.7360 -0.0901 0.4978 0.030 Uiso 1 1 calc R U . . .
C12 C 0.79409(18) 0.0618(9) 0.4418(4) 0.0246(11) Uani 1 1 d . . . . .
H12 H 0.7960 -0.0610 0.3880 0.029 Uiso 1 1 calc R U . . .
C13 C 0.71549(18) 0.2054(9) 0.6594(4) 0.0256(11) Uani 1 1 d . . . . .
H13 H 0.7232 0.3344 0.7185 0.031 Uiso 1 1 calc R U . . .
C14 C 0.71610(19) -0.0381(10) 0.7211(4) 0.0305(12) Uani 1 1 d . . . . .
H14A H 0.7099 -0.1701 0.6645 0.037 Uiso 1 1 calc R U . . .
H14B H 0.7497 -0.0639 0.7699 0.037 Uiso 1 1 calc R U . . .
C15 C 0.67680(18) -0.0489(10) 0.7934(4) 0.0286(12) Uani 1 1 d . . . . .
H15A H 0.6853 0.0712 0.8552 0.034 Uiso 1 1 calc R U . . .
H15B H 0.6776 -0.2110 0.8284 0.034 Uiso 1 1 calc R U . . .
C16 C 0.62394(18) 0.0009(10) 0.7259(4) 0.0270(11) Uani 1 1 d . . . . .
H16 H 0.6151 -0.1300 0.6681 0.032 Uiso 1 1 calc R U . . .
C17 C 0.62337(19) 0.2404(10) 0.6629(5) 0.0331(13) Uani 1 1 d . . . . .
H17A H 0.6294 0.3738 0.7187 0.040 Uiso 1 1 calc R U . . .
H17B H 0.5897 0.2647 0.6141 0.040 Uiso 1 1 calc R U . . .
C18 C 0.66250(18) 0.2533(10) 0.5897(4) 0.0291(12) Uani 1 1 d . . . . .
H18A H 0.6614 0.4152 0.5545 0.035 Uiso 1 1 calc R U . . .
H18B H 0.6544 0.1322 0.5282 0.035 Uiso 1 1 calc R U . . .
C19 C 0.58474(19) -0.0002(10) 0.7986(4) 0.0312(12) Uani 1 1 d . . . . .
H19A H 0.5943 0.1218 0.8593 0.037 Uiso 1 1 calc R U . . .
H19B H 0.5523 0.0506 0.7510 0.037 Uiso 1 1 calc R U . . .
C20 C 0.5775(2) -0.2406(11) 0.8527(5) 0.0413(14) Uani 1 1 d . . . . .
H20A H 0.6100 -0.2946 0.8991 0.050 Uiso 1 1 calc R U . . .
H20B H 0.5665 -0.3622 0.7925 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5393(2) -0.2285(13) 0.9269(5) 0.0453(16) Uani 1 1 d . . . . .
H21A H 0.5075 -0.1666 0.8825 0.054 Uiso 1 1 calc R U . . .
H21B H 0.5515 -0.1205 0.9910 0.054 Uiso 1 1 calc R U . . .
H21C H 0.5341 -0.3905 0.9550 0.054 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.396(6) . ?
F2 C2 1.381(6) . ?
F3 C5 1.409(6) . ?
C1 C6 1.512(7) . ?
C1 C2 1.517(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.509(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.520(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.512(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.529(7) . ?
C5 H5 1.0000 . ?
C6 C7 1.529(6) . ?
C6 H6 1.0000 . ?
C7 C8 1.385(7) . ?
C7 C12 1.391(7) . ?
C8 C9 1.404(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(7) . ?
C10 C13 1.515(7) . ?
C11 C12 1.390(7) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.536(7) . ?
C13 C14 1.538(7) . ?
C13 H13 1.0000 . ?
C14 C15 1.524(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C19 1.524(7) . ?
C16 C17 1.527(7) . ?
C16 H16 1.0000 . ?
C17 C18 1.529(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.514(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C6 111.9(4) . . ?
F1 C1 C2 107.3(4) . . ?
C6 C1 C2 111.4(4) . . ?
F1 C1 H1 108.8 . . ?
C6 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
F2 C2 C3 109.9(4) . . ?
F2 C2 C1 109.5(4) . . ?
C3 C2 C1 112.1(4) . . ?
F2 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C2 C3 C4 109.1(4) . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C5 C4 C3 112.4(4) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
F3 C5 C4 107.9(4) . . ?
F3 C5 C6 109.7(4) . . ?
C4 C5 C6 112.2(4) . . ?
F3 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C1 C6 C5 112.0(4) . . ?
C1 C6 C7 114.7(4) . . ?
C5 C6 C7 112.8(4) . . ?
C1 C6 H6 105.4 . . ?
C5 C6 H6 105.4 . . ?
C7 C6 H6 105.4 . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 C6 122.5(4) . . ?
C12 C7 C6 119.0(4) . . ?
C7 C8 C9 119.6(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 122.4(4) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 117.4(4) . . ?
C9 C10 C13 121.2(4) . . ?
C11 C10 C13 121.4(4) . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C10 C13 C18 111.7(4) . . ?
C10 C13 C14 113.2(4) . . ?
C18 C13 C14 109.2(4) . . ?
C10 C13 H13 107.5 . . ?
C18 C13 H13 107.5 . . ?
C14 C13 H13 107.5 . . ?
C15 C14 C13 112.1(4) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.9(4) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C19 C16 C15 113.1(4) . . ?
C19 C16 C17 110.9(4) . . ?
C15 C16 C17 109.4(4) . . ?
C19 C16 H16 107.7 . . ?
C15 C16 H16 107.7 . . ?
C17 C16 H16 107.7 . . ?
C16 C17 C18 113.3(4) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C13 111.6(4) . . ?
C17 C18 H18A 109.3 . . ?
C13 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C13 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C16 115.2(4) . . ?
C20 C19 H19A 108.5 . . ?
C16 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C16 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 112.8(5) . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 -56.2(5) . . . . ?
C6 C1 C2 F2 -178.9(4) . . . . ?
F1 C1 C2 C3 66.1(5) . . . . ?
C6 C1 C2 C3 -56.6(6) . . . . ?
F2 C2 C3 C4 180.0(4) . . . . ?
C1 C2 C3 C4 57.9(6) . . . . ?
C2 C3 C4 C5 -56.3(6) . . . . ?
C3 C4 C5 F3 -67.7(6) . . . . ?
C3 C4 C5 C6 53.3(6) . . . . ?
F1 C1 C6 C5 -68.3(5) . . . . ?
C2 C1 C6 C5 51.7(5) . . . . ?
F1 C1 C6 C7 62.1(5) . . . . ?
C2 C1 C6 C7 -177.9(4) . . . . ?
F3 C5 C6 C1 69.5(5) . . . . ?
C4 C5 C6 C1 -50.5(6) . . . . ?
F3 C5 C6 C7 -61.8(5) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C1 C6 C7 C8 -58.2(6) . . . . ?
C5 C6 C7 C8 71.8(6) . . . . ?
C1 C6 C7 C12 124.5(5) . . . . ?
C5 C6 C7 C12 -105.6(5) . . . . ?
C12 C7 C8 C9 0.4(7) . . . . ?
C6 C7 C8 C9 -177.0(4) . . . . ?
C7 C8 C9 C10 0.5(7) . . . . ?
C8 C9 C10 C11 -1.2(7) . . . . ?
C8 C9 C10 C13 179.8(5) . . . . ?
C9 C10 C11 C12 0.9(7) . . . . ?
C13 C10 C11 C12 179.9(5) . . . . ?
C10 C11 C12 C7 -0.1(7) . . . . ?
C8 C7 C12 C11 -0.6(7) . . . . ?
C6 C7 C12 C11 176.9(4) . . . . ?
C9 C10 C13 C18 107.4(5) . . . . ?
C11 C10 C13 C18 -71.5(6) . . . . ?
C9 C10 C13 C14 -128.8(5) . . . . ?
C11 C10 C13 C14 52.2(6) . . . . ?
C10 C13 C14 C15 179.7(4) . . . . ?
C18 C13 C14 C15 -55.2(5) . . . . ?
C13 C14 C15 C16 56.2(6) . . . . ?
C14 C15 C16 C19 -177.8(5) . . . . ?
C14 C15 C16 C17 -53.6(6) . . . . ?
C19 C16 C17 C18 179.2(5) . . . . ?
C15 C16 C17 C18 53.7(6) . . . . ?
C16 C17 C18 C13 -56.0(6) . . . . ?
C10 C13 C18 C17 -179.2(4) . . . . ?
C14 C13 C18 C17 54.8(6) . . . . ?
C15 C16 C19 C20 -64.3(6) . . . . ?
C17 C16 C19 C20 172.4(5) . . . . ?
C16 C19 C20 C21 178.2(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1503422'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-02
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H30 F2'
_chemical_formula_moiety         'C21 H30 F2'
_chemical_formula_weight         320.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P2/c
_space_group_name_Hall           '-P 2yc'
_space_group_IT_number           13
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.934(3)
_cell_length_b                   5.5818(15)
_cell_length_c                   26.703(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.656(6)
_cell_angle_gamma                90.0000
_cell_volume                     1778.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1336
_cell_measurement_theta_min      1.50
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            19791
_diffrn_reflns_av_R_equivalents  0.1637
_diffrn_reflns_theta_max         25.380
_diffrn_reflns_theta_min         1.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3250
_reflns_number_gt                1474
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2025
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.1732
_refine_ls_wR_factor_gt          0.1331
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3250
_refine_ls_number_parameters     228
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0462P)²+1.2477P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9313(3) -0.3605(5) 0.34185(12) 0.0651(12) Uani 0.742(4) 1 d . . P A 1
F2 F 1.1524(3) -0.3612(6) 0.36773(11) 0.0640(11) Uani 0.742(4) 1 d . . P A 1
F1A F 0.8168(7) -0.0626(16) 0.3923(3) 0.053(3) Uani 0.258(4) 1 d . . P A 2
F2A F 0.9569(9) 0.1699(19) 0.4588(3) 0.075(4) Uani 0.258(4) 1 d . . P A 2
C1 C 0.9965(3) -0.1729(8) 0.32871(15) 0.0478(11) Uani 1 1 d . . . . .
H1A H 1.0289 -0.2019 0.2949 0.057 Uiso 0.742(4) 1 calc R U P A 1
H1B H 0.9467 -0.3097 0.3362 0.057 Uiso 0.258(4) 1 calc R U P A 2
H1C H 1.0292 -0.1996 0.2953 0.057 Uiso 0.258(4) 1 calc R U P A 2
C2 C 1.0884(3) -0.1612(8) 0.36712(15) 0.0529(12) Uani 1 1 d . . . . .
H2A H 1.1382 -0.0244 0.3579 0.064 Uiso 0.742(4) 1 calc R U P A 1
H2B H 1.1300 -0.3147 0.3670 0.064 Uiso 0.258(4) 1 calc R U P A 2
H2C H 1.1414 -0.0327 0.3577 0.064 Uiso 0.258(4) 1 calc R U P A 2
C3 C 1.0477(3) -0.1147(7) 0.41880(14) 0.0491(11) Uani 1 1 d . . . . .
H3A H 1.1122 -0.0985 0.4422 0.059 Uiso 1 1 calc R U . . .
H3B H 1.0010 -0.2505 0.4301 0.059 Uiso 1 1 calc R U . . .
C4 C 0.9790(4) 0.1147(8) 0.41868(18) 0.0591(13) Uani 1 1 d . . . . .
H4A H 0.9469 0.1393 0.4523 0.071 Uiso 0.742(4) 1 calc R U P A 1
H4B H 1.0287 0.2521 0.4115 0.071 Uiso 0.742(4) 1 calc R U P A 1
H4C H 1.0313 0.2418 0.4067 0.071 Uiso 0.258(4) 1 calc R U P A 2
C5 C 0.8853(3) 0.1076(7) 0.38025(14) 0.0465(11) Uani 1 1 d . . . . .
H5A H 0.8455 0.2632 0.3803 0.056 Uiso 0.742(4) 1 calc R U P A 1
H5B H 0.8311 -0.0184 0.3896 0.056 Uiso 0.742(4) 1 calc R U P A 1
H5C H 0.8446 0.2642 0.3803 0.056 Uiso 0.258(4) 1 calc R U P A 2
C6 C 0.9283(3) 0.0577(6) 0.32800(14) 0.0364(10) Uani 1 1 d . . . . .
H6 H 0.9821 0.1895 0.3203 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8381(3) 0.0678(6) 0.28784(13) 0.0340(9) Uani 1 1 d . . . . .
C8 C 0.7545(3) -0.1040(7) 0.28260(14) 0.0394(10) Uani 1 1 d . . . . .
H8 H 0.7544 -0.2385 0.3044 0.047 Uiso 1 1 calc R U . . .
C9 C 0.6719(3) -0.0834(7) 0.24659(14) 0.0403(10) Uani 1 1 d . . . . .
H9 H 0.6168 -0.2059 0.2440 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6657(3) 0.1097(6) 0.21377(13) 0.0334(9) Uani 1 1 d . . . . .
C11 C 0.7494(3) 0.2829(6) 0.21954(13) 0.0369(10) Uani 1 1 d . . . . .
H11 H 0.7488 0.4192 0.1982 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8326(3) 0.2613(6) 0.25523(14) 0.0373(10) Uani 1 1 d . . . . .
H12 H 0.8882 0.3826 0.2577 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5758(3) 0.1297(6) 0.17432(13) 0.0350(9) Uani 1 1 d . . . . .
H13 H 0.5183 0.0044 0.1816 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6196(3) 0.0809(7) 0.12207(13) 0.0429(10) Uani 1 1 d . . . . .
H14A H 0.6536 -0.0808 0.1213 0.051 Uiso 1 1 calc R U . . .
H14B H 0.6788 0.1988 0.1143 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5274(3) 0.0958(7) 0.08224(14) 0.0436(10) Uani 1 1 d . . . . .
H15A H 0.4728 -0.0347 0.0878 0.052 Uiso 1 1 calc R U . . .
H15B H 0.5608 0.0710 0.0489 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4656(3) 0.3359(6) 0.08250(13) 0.0365(10) Uani 1 1 d . . . . .
H16 H 0.5214 0.4636 0.0745 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4229(3) 0.3843(7) 0.13485(13) 0.0435(10) Uani 1 1 d . . . . .
H17A H 0.3879 0.5450 0.1357 0.052 Uiso 1 1 calc R U . . .
H17B H 0.3646 0.2649 0.1431 0.052 Uiso 1 1 calc R U . . .
C18 C 0.5156(3) 0.3729(7) 0.17400(13) 0.0431(10) Uani 1 1 d . . . . .
H18A H 0.4834 0.4023 0.2074 0.052 Uiso 1 1 calc R U . . .
H18B H 0.5707 0.5011 0.1674 0.052 Uiso 1 1 calc R U . . .
C19 C 0.3744(3) 0.3433(7) 0.04208(13) 0.0424(10) Uani 1 1 d . . . . .
H19A H 0.4085 0.2997 0.0097 0.051 Uiso 1 1 calc R U . . .
H19B H 0.3178 0.2195 0.0499 0.051 Uiso 1 1 calc R U . . .
C20 C 0.3148(3) 0.5811(7) 0.03574(16) 0.0529(12) Uani 1 1 d . . . . .
H20A H 0.3711 0.7063 0.0285 0.063 Uiso 1 1 calc R U . . .
H20B H 0.2786 0.6233 0.0677 0.063 Uiso 1 1 calc R U . . .
C21 C 0.2268(3) 0.5828(8) -0.00557(15) 0.0613(13) Uani 1 1 d . . . . .
H21A H 0.1665 0.4710 0.0029 0.074 Uiso 1 1 calc R U . . .
H21B H 0.2609 0.5338 -0.0372 0.074 Uiso 1 1 calc R U . . .
H21C H 0.1959 0.7447 -0.0091 0.074 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.354(5) . ?
F2 C2 1.352(5) . ?
F1A C5 1.297(8) . ?
F2A C4 1.148(9) . ?
C1 C2 1.495(5) . ?
C1 C6 1.523(5) . ?
C1 H1A 1.0000 . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C2 C3 1.491(5) . ?
C2 H2A 1.0000 . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C4 1.520(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.510(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 H4C 1.0000 . ?
C5 C6 1.518(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5C 1.0000 . ?
C6 C7 1.511(5) . ?
C6 H6 1.0000 . ?
C7 C12 1.388(5) . ?
C7 C8 1.390(5) . ?
C8 C9 1.374(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(5) . ?
C10 C13 1.500(5) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.520(5) . ?
C13 C18 1.536(5) . ?
C13 H13 1.0000 . ?
C14 C15 1.524(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(5) . ?
C16 C19 1.524(5) . ?
C16 H16 1.0000 . ?
C17 C18 1.514(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.514(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.515(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 106.0(4) . . ?
F1 C1 C6 110.4(3) . . ?
C2 C1 C6 111.1(4) . . ?
F1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
C6 C1 H1A 109.8 . . ?
C2 C1 H1B 109.4 . . ?
C6 C1 H1B 109.4 . . ?
C2 C1 H1C 109.4 . . ?
C6 C1 H1C 109.4 . . ?
H1B C1 H1C 108.0 . . ?
F2 C2 C3 108.8(3) . . ?
F2 C2 C1 112.5(4) . . ?
C3 C2 C1 113.5(3) . . ?
F2 C2 H2A 107.3 . . ?
C3 C2 H2A 107.3 . . ?
C1 C2 H2A 107.3 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2C 108.9 . . ?
C1 C2 H2C 108.9 . . ?
H2B C2 H2C 107.7 . . ?
C2 C3 C4 109.0(4) . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
F2A C4 C5 117.7(7) . . ?
F2A C4 C3 110.8(6) . . ?
C5 C4 C3 112.0(4) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
F2A C4 H4C 105.1 . . ?
C5 C4 H4C 105.1 . . ?
C3 C4 H4C 105.1 . . ?
F1A C5 C4 108.4(5) . . ?
F1A C5 C6 108.3(5) . . ?
C4 C5 C6 112.0(4) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
F1A C5 H5C 109.4 . . ?
C4 C5 H5C 109.4 . . ?
C6 C5 H5C 109.4 . . ?
C7 C6 C5 113.6(3) . . ?
C7 C6 C1 114.6(3) . . ?
C5 C6 C1 109.3(3) . . ?
C7 C6 H6 106.2 . . ?
C5 C6 H6 106.2 . . ?
C1 C6 H6 106.2 . . ?
C12 C7 C8 116.4(3) . . ?
C12 C7 C6 120.2(3) . . ?
C8 C7 C6 123.4(3) . . ?
C9 C8 C7 121.4(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 122.5(4) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C9 C10 C11 115.7(3) . . ?
C9 C10 C13 122.2(3) . . ?
C11 C10 C13 122.1(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 122.2(3) . . ?
C11 C12 H12 118.9 . . ?
C7 C12 H12 118.9 . . ?
C10 C13 C14 112.4(3) . . ?
C10 C13 C18 113.6(3) . . ?
C14 C13 C18 108.6(3) . . ?
C10 C13 H13 107.3 . . ?
C14 C13 H13 107.3 . . ?
C18 C13 H13 107.3 . . ?
C13 C14 C15 112.2(3) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.9(3) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C19 113.8(3) . . ?
C17 C16 C15 109.1(3) . . ?
C19 C16 C15 111.2(3) . . ?
C17 C16 H16 107.5 . . ?
C19 C16 H16 107.5 . . ?
C15 C16 H16 107.5 . . ?
C18 C17 C16 112.2(3) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C13 112.3(3) . . ?
C17 C18 H18A 109.1 . . ?
C13 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C13 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C16 115.7(3) . . ?
C20 C19 H19A 108.4 . . ?
C16 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
C16 C19 H19B 108.4 . . ?
H19A C19 H19B 107.4 . . ?
C19 C20 C21 114.1(3) . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 61.7(5) . . . . ?
C6 C1 C2 F2 -178.4(3) . . . . ?
F1 C1 C2 C3 -62.3(5) . . . . ?
C6 C1 C2 C3 57.6(5) . . . . ?
F2 C2 C3 C4 178.1(4) . . . . ?
C1 C2 C3 C4 -55.9(5) . . . . ?
C2 C3 C4 F2A -172.0(7) . . . . ?
C2 C3 C4 C5 54.5(5) . . . . ?
F2A C4 C5 F1A -66.6(9) . . . . ?
C3 C4 C5 F1A 63.4(6) . . . . ?
F2A C4 C5 C6 174.0(8) . . . . ?
C3 C4 C5 C6 -56.0(5) . . . . ?
F1A C5 C6 C7 65.0(6) . . . . ?
C4 C5 C6 C7 -175.6(3) . . . . ?
F1A C5 C6 C1 -64.4(5) . . . . ?
C4 C5 C6 C1 55.0(5) . . . . ?
F1 C1 C6 C7 -66.6(4) . . . . ?
C2 C1 C6 C7 176.2(3) . . . . ?
F1 C1 C6 C5 62.2(4) . . . . ?
C2 C1 C6 C5 -55.0(4) . . . . ?
C5 C6 C7 C12 106.0(4) . . . . ?
C1 C6 C7 C12 -127.4(4) . . . . ?
C5 C6 C7 C8 -70.9(5) . . . . ?
C1 C6 C7 C8 55.7(5) . . . . ?
C12 C7 C8 C9 0.7(5) . . . . ?
C6 C7 C8 C9 177.8(4) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C8 C9 C10 C13 179.5(4) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C13 C10 C11 C12 -178.9(3) . . . . ?
C10 C11 C12 C7 -0.5(6) . . . . ?
C8 C7 C12 C11 -0.1(5) . . . . ?
C6 C7 C12 C11 -177.2(4) . . . . ?
C9 C10 C13 C14 -106.4(4) . . . . ?
C11 C10 C13 C14 72.9(4) . . . . ?
C9 C10 C13 C18 129.8(4) . . . . ?
C11 C10 C13 C18 -50.9(5) . . . . ?
C10 C13 C14 C15 178.7(3) . . . . ?
C18 C13 C14 C15 -54.7(4) . . . . ?
C13 C14 C15 C16 55.9(4) . . . . ?
C14 C15 C16 C17 -53.9(4) . . . . ?
C14 C15 C16 C19 179.9(3) . . . . ?
C19 C16 C17 C18 179.4(3) . . . . ?
C15 C16 C17 C18 54.7(4) . . . . ?
C16 C17 C18 C13 -57.7(4) . . . . ?
C10 C13 C18 C17 -178.2(3) . . . . ?
C14 C13 C18 C17 56.0(4) . . . . ?
C17 C16 C19 C20 61.8(5) . . . . ?
C15 C16 C19 C20 -174.6(3) . . . . ?
C16 C19 C20 C21 178.6(4) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1503423'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-02
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H31 F'
_chemical_formula_moiety         'C21 H31 F'
_chemical_formula_weight         302.47
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.3032(6)
_cell_length_b                   25.832(3)
_cell_length_c                   13.1164(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.667(3)
_cell_angle_gamma                90.0000
_cell_volume                     1780.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4831
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664.00
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            21702
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_theta_max         25.374
_diffrn_reflns_theta_min         1.577
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3277
_reflns_number_gt                2588
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1468
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3277
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0790P)²+0.5173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.0514(4) 0.24672(7) 0.60659(15) 0.0785(8) Uani 0.735(4) 1 d . . P A 1
F1A F 1.1384(9) 0.1828(2) 0.7331(4) 0.087(2) Uani 0.265(4) 1 d . . P A 2
C1 C 0.7980(5) 0.25144(8) 0.62893(16) 0.0606(6) Uani 1 1 d . . . . .
H1A H 0.6866 0.2641 0.5664 0.073 Uiso 0.735(4) 1 calc R U P A 1
H1B H 0.6865 0.2640 0.5673 0.073 Uiso 0.265(4) 1 calc R U P A 2
H1C H 0.9737 0.2494 0.6115 0.073 Uiso 0.265(4) 1 calc R U P A 2
C2 C 0.7134(3) 0.19845(7) 0.65605(13) 0.0420(4) Uani 1 1 d . . . . .
H2 H 0.5356 0.2025 0.6725 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8729(5) 0.17961(8) 0.75577(14) 0.0622(6) Uani 1 1 d . . . . .
H3A H 0.8111 0.1453 0.7751 0.075 Uiso 0.735(4) 1 calc R U P A 1
H3B H 1.0531 0.1760 0.7448 0.075 Uiso 0.735(4) 1 calc R U P A 1
H3C H 0.8258 0.1437 0.7747 0.075 Uiso 0.265(4) 1 calc R U P A 2
C4 C 0.8518(6) 0.21836(9) 0.84230(16) 0.0719(7) Uani 1 1 d . . . . .
H4A H 0.6731 0.2197 0.8563 0.086 Uiso 1 1 calc R U . . .
H4B H 0.9580 0.2063 0.9057 0.086 Uiso 1 1 calc R U . . .
C5 C 0.9348(4) 0.27142(8) 0.81629(17) 0.0586(5) Uani 1 1 d . . . . .
H5A H 1.1193 0.2711 0.8111 0.070 Uiso 1 1 calc R U . . .
H5B H 0.9054 0.2957 0.8719 0.070 Uiso 1 1 calc R U . . .
C6 C 0.7907(6) 0.28981(9) 0.71587(17) 0.0727(7) Uani 1 1 d . . . . .
H6A H 0.8641 0.3231 0.6966 0.087 Uiso 1 1 calc R U . . .
H6B H 0.6113 0.2962 0.7254 0.087 Uiso 1 1 calc R U . . .
C7 C 0.6978(3) 0.16083(7) 0.56674(12) 0.0372(4) Uani 1 1 d . . . . .
C8 C 0.8825(3) 0.12386(7) 0.55594(12) 0.0401(4) Uani 1 1 d . . . . .
H8 H 1.0308 0.1223 0.6052 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8547(3) 0.08924(7) 0.47488(13) 0.0404(4) Uani 1 1 d . . . . .
H9 H 0.9842 0.0643 0.4699 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6416(3) 0.09001(6) 0.40037(12) 0.0353(4) Uani 1 1 d . . . . .
C11 C 0.4597(3) 0.12777(7) 0.40998(13) 0.0403(4) Uani 1 1 d . . . . .
H11 H 0.3138 0.1300 0.3596 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4865(3) 0.16220(7) 0.49128(13) 0.0425(4) Uani 1 1 d . . . . .
H12 H 0.3580 0.1874 0.4958 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6018(3) 0.05050(6) 0.31459(12) 0.0357(4) Uani 1 1 d . . . . .
H13 H 0.4436 0.0605 0.2686 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8167(3) 0.04823(7) 0.24805(13) 0.0411(4) Uani 1 1 d . . . . .
H14A H 0.8434 0.0831 0.2202 0.049 Uiso 1 1 calc R U . . .
H14B H 0.9761 0.0377 0.2911 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7579(3) 0.01017(7) 0.15924(13) 0.0410(4) Uani 1 1 d . . . . .
H15A H 0.9037 0.0091 0.1194 0.049 Uiso 1 1 calc R U . . .
H15B H 0.6075 0.0226 0.1128 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7056(3) -0.04443(6) 0.19577(12) 0.0359(4) Uani 1 1 d . . . . .
H16 H 0.8663 -0.0580 0.2353 0.043 Uiso 1 1 calc R U . . .
C17 C 0.5035(4) -0.04284(7) 0.26802(13) 0.0448(4) Uani 1 1 d . . . . .
H17A H 0.4885 -0.0777 0.2979 0.054 Uiso 1 1 calc R U . . .
H17B H 0.3376 -0.0342 0.2276 0.054 Uiso 1 1 calc R U . . .
C18 C 0.5587(3) -0.00385(7) 0.35531(13) 0.0430(4) Uani 1 1 d . . . . .
H18A H 0.7119 -0.0149 0.4017 0.052 Uiso 1 1 calc R U . . .
H18B H 0.4138 -0.0031 0.3957 0.052 Uiso 1 1 calc R U . . .
C19 C 0.6254(3) -0.08164(7) 0.10653(13) 0.0426(4) Uani 1 1 d . . . . .
H19A H 0.5932 -0.1160 0.1358 0.051 Uiso 1 1 calc R U . . .
H19B H 0.4620 -0.0692 0.0692 0.051 Uiso 1 1 calc R U . . .
C20 C 0.8103(4) -0.08884(8) 0.02918(15) 0.0519(5) Uani 1 1 d . . . . .
H20A H 0.9767 -0.1001 0.0656 0.062 Uiso 1 1 calc R U . . .
H20B H 0.8357 -0.0552 -0.0043 0.062 Uiso 1 1 calc R U . . .
C21 C 0.7165(5) -0.12858(9) -0.05293(17) 0.0690(6) Uani 1 1 d . . . . .
H21A H 0.5516 -0.1176 -0.0892 0.083 Uiso 1 1 calc R U . . .
H21B H 0.6978 -0.1623 -0.0204 0.083 Uiso 1 1 calc R U . . .
H21C H 0.8397 -0.1315 -0.1021 0.083 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.418(3) . ?
F1A C3 1.480(6) . ?
C1 C2 1.498(3) . ?
C1 C6 1.515(3) . ?
C1 H1A 1.0000 . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C2 C7 1.516(2) . ?
C2 C3 1.539(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 H3C 1.0000 . ?
C4 C5 1.493(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.509(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.389(2) . ?
C7 C12 1.393(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 C13 1.513(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.526(2) . ?
C13 C18 1.530(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.524(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.527(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(2) . ?
C16 C19 1.530(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.524(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.514(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 107.01(16) . . ?
F1 C1 C6 109.4(2) . . ?
C2 C1 C6 112.37(17) . . ?
F1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C6 C1 H1A 109.3 . . ?
C2 C1 H1B 109.1 . . ?
C6 C1 H1B 109.1 . . ?
C2 C1 H1C 109.1 . . ?
C6 C1 H1C 109.1 . . ?
H1B C1 H1C 107.9 . . ?
C1 C2 C7 112.93(14) . . ?
C1 C2 C3 110.05(16) . . ?
C7 C2 C3 114.92(15) . . ?
C1 C2 H2 106.1 . . ?
C7 C2 H2 106.1 . . ?
C3 C2 H2 106.1 . . ?
F1A C3 C4 106.1(3) . . ?
F1A C3 C2 104.0(3) . . ?
C4 C3 C2 109.74(18) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
F1A C3 H3C 112.2 . . ?
C4 C3 H3C 112.2 . . ?
C2 C3 H3C 112.2 . . ?
C5 C4 C3 112.24(19) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 110.99(18) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C1 112.96(19) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C12 117.16(15) . . ?
C8 C7 C2 123.57(15) . . ?
C12 C7 C2 119.26(15) . . ?
C9 C8 C7 121.28(15) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.60(16) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 117.05(15) . . ?
C11 C10 C13 120.76(14) . . ?
C9 C10 C13 122.15(15) . . ?
C12 C11 C10 121.39(15) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 121.49(16) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C10 C13 C14 114.24(13) . . ?
C10 C13 C18 111.84(13) . . ?
C14 C13 C18 108.79(14) . . ?
C10 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C18 C13 H13 107.2 . . ?
C15 C14 C13 111.68(13) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.53(13) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 110.04(14) . . ?
C17 C16 C19 110.24(13) . . ?
C15 C16 C19 112.58(13) . . ?
C17 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C19 C16 H16 107.9 . . ?
C16 C17 C18 113.88(14) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C13 111.53(14) . . ?
C17 C18 H18A 109.3 . . ?
C13 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C13 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C16 116.81(15) . . ?
C20 C19 H19A 108.1 . . ?
C16 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
C16 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 C21 112.17(17) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C7 -64.9(2) . . . . ?
C6 C1 C2 C7 174.99(18) . . . . ?
F1 C1 C2 C3 65.0(2) . . . . ?
C6 C1 C2 C3 -55.1(2) . . . . ?
C1 C2 C3 F1A -56.4(3) . . . . ?
C7 C2 C3 F1A 72.4(3) . . . . ?
C1 C2 C3 C4 56.8(2) . . . . ?
C7 C2 C3 C4 -174.37(17) . . . . ?
F1A C3 C4 C5 54.2(4) . . . . ?
C2 C3 C4 C5 -57.6(3) . . . . ?
C3 C4 C5 C6 54.7(3) . . . . ?
C4 C5 C6 C1 -51.9(3) . . . . ?
F1 C1 C6 C5 -65.5(3) . . . . ?
C2 C1 C6 C5 53.1(3) . . . . ?
C1 C2 C7 C8 101.3(2) . . . . ?
C3 C2 C7 C8 -26.0(2) . . . . ?
C1 C2 C7 C12 -79.6(2) . . . . ?
C3 C2 C7 C12 152.98(17) . . . . ?
C12 C7 C8 C9 -1.4(2) . . . . ?
C2 C7 C8 C9 177.67(16) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C8 C9 C10 C13 -176.54(15) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C13 C10 C11 C12 176.19(16) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C2 C7 C12 C11 -178.09(16) . . . . ?
C11 C10 C13 C14 125.00(17) . . . . ?
C9 C10 C13 C14 -57.4(2) . . . . ?
C11 C10 C13 C18 -110.88(17) . . . . ?
C9 C10 C13 C18 66.7(2) . . . . ?
C10 C13 C14 C15 -176.48(14) . . . . ?
C18 C13 C14 C15 57.79(18) . . . . ?
C13 C14 C15 C16 -57.10(19) . . . . ?
C14 C15 C16 C17 51.94(19) . . . . ?
C14 C15 C16 C19 175.34(14) . . . . ?
C15 C16 C17 C18 -51.2(2) . . . . ?
C19 C16 C17 C18 -175.95(15) . . . . ?
C16 C17 C18 C13 54.7(2) . . . . ?
C10 C13 C18 C17 176.70(14) . . . . ?
C14 C13 C18 C17 -56.19(18) . . . . ?
C17 C16 C19 C20 -178.24(16) . . . . ?
C15 C16 C19 C20 58.5(2) . . . . ?
C16 C19 C20 C21 177.19(16) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1503424'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-01
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H28 O2'
_chemical_formula_moiety         'C21 H28 O2'
_chemical_formula_weight         312.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.4875(6)
_cell_length_b                   9.8366(9)
_cell_length_c                   16.6611(15)
_cell_angle_alpha                79.139(11)
_cell_angle_beta                 84.202(15)
_cell_angle_gamma                79.462(15)
_cell_volume                     866.27(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1085
_cell_measurement_theta_min      23.98
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    124
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340.00
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.994

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      124
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            3048
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_theta_max         68.278
_diffrn_reflns_theta_min         4.643
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt)., Twin
;
_reflns_number_total             3048
_reflns_number_gt                2749
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1604
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3048
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0736P)²+0.4931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.1956(3) 0.11086(16) 1.14462(9) 0.0274(4) Uani 1 1 d . . . . .
O2 O 0.8481(3) 0.35967(16) 1.17825(9) 0.0317(4) Uani 1 1 d . . . . .
C1 C 0.9673(4) 0.0542(2) 1.14991(12) 0.0248(5) Uani 1 1 d . . . . .
H1 H 0.9883 -0.0495 1.1519 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7518(4) 0.1154(2) 1.20194(13) 0.0275(5) Uani 1 1 d . . . . .
H2A H 0.7980 0.0955 1.2594 0.033 Uiso 1 1 calc R U . . .
H2B H 0.6106 0.0666 1.1997 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6653(4) 0.2705(2) 1.17864(13) 0.0275(5) Uani 1 1 d . . . . .
H3 H 0.4932 0.3066 1.1999 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7558(4) 0.3513(2) 1.10177(12) 0.0255(5) Uani 1 1 d . . . . .
H4 H 0.6367 0.4353 1.0779 0.031 Uiso 1 1 calc R U . . .
C5 C 0.9394(4) 0.2845(2) 1.04057(12) 0.0218(4) Uani 1 1 d . . . . .
H5 H 1.0750 0.3420 1.0257 0.026 Uiso 1 1 calc R U . . .
C6 C 1.0575(4) 0.1350(2) 1.07279(12) 0.0225(5) Uani 1 1 d . . . . .
H6 H 1.1315 0.0781 1.0298 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8133(4) 0.2869(2) 0.96304(12) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.8852(4) 0.3653(2) 0.88886(12) 0.0227(4) Uani 1 1 d . . . . .
H8 H 1.0129 0.4196 0.8868 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7734(4) 0.3655(2) 0.81794(12) 0.0230(5) Uani 1 1 d . . . . .
H9 H 0.8249 0.4205 0.7681 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5860(4) 0.2862(2) 0.81836(12) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.5133(4) 0.2086(2) 0.89326(12) 0.0219(4) Uani 1 1 d . . . . .
H11 H 0.3855 0.1544 0.8954 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6235(4) 0.2090(2) 0.96444(12) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.5696 0.1559 1.0146 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4670(4) 0.2816(2) 0.74107(12) 0.0225(5) Uani 1 1 d . . . . .
H13 H 0.3078 0.2449 0.7581 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4029(4) 0.4261(2) 0.68751(12) 0.0265(5) Uani 1 1 d . . . . .
H14A H 0.2958 0.4910 0.7202 0.032 Uiso 1 1 calc R U . . .
H14B H 0.5573 0.4646 0.6685 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2685(4) 0.4156(2) 0.61372(12) 0.0271(5) Uani 1 1 d . . . . .
H15A H 0.2338 0.5099 0.5794 0.032 Uiso 1 1 calc R U . . .
H15B H 0.1072 0.3853 0.6332 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4164(4) 0.3132(2) 0.56131(12) 0.0253(5) Uani 1 1 d . . . . .
H16 H 0.5691 0.3511 0.5363 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4969(5) 0.1703(2) 0.61469(13) 0.0285(5) Uani 1 1 d . . . . .
H17A H 0.6096 0.1089 0.5811 0.034 Uiso 1 1 calc R U . . .
H17B H 0.3485 0.1258 0.6336 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6293(4) 0.1811(2) 0.68944(12) 0.0244(5) Uani 1 1 d . . . . .
H18A H 0.7880 0.2153 0.6709 0.029 Uiso 1 1 calc R U . . .
H18B H 0.6681 0.0869 0.7235 0.029 Uiso 1 1 calc R U . . .
C19 C 0.2597(5) 0.3043(2) 0.49196(13) 0.0311(5) Uani 1 1 d . . . . .
H19A H 0.1109 0.2643 0.5168 0.037 Uiso 1 1 calc R U . . .
H19B H 0.2011 0.4010 0.4637 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3851(5) 0.2185(2) 0.42768(13) 0.0331(5) Uani 1 1 d . . . . .
H20A H 0.4487 0.1217 0.4548 0.040 Uiso 1 1 calc R U . . .
H20B H 0.5284 0.2605 0.3995 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2054(5) 0.2132(3) 0.36468(15) 0.0393(6) Uani 1 1 d . . . . .
H21A H 0.1454 0.3087 0.3367 0.047 Uiso 1 1 calc R U . . .
H21B H 0.0642 0.1708 0.3924 0.047 Uiso 1 1 calc R U . . .
H21C H 0.2910 0.1567 0.3245 0.047 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C6 1.440(2) . ?
O1 C1 1.450(2) . ?
O2 C4 1.439(2) . ?
O2 C3 1.447(3) . ?
C1 C6 1.469(3) . ?
C1 C2 1.497(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.501(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.466(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.513(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.515(3) . ?
C5 C7 1.520(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.390(3) . ?
C7 C12 1.397(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(3) . ?
C10 C13 1.513(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.530(3) . ?
C13 C18 1.534(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.524(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.531(3) . ?
C16 C19 1.533(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.534(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.521(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.525(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C1 61.12(12) . . ?
C4 O2 C3 61.06(13) . . ?
O1 C1 C6 59.09(12) . . ?
O1 C1 C2 117.55(17) . . ?
C6 C1 C2 121.75(18) . . ?
O1 C1 H1 115.5 . . ?
C6 C1 H1 115.5 . . ?
C2 C1 H1 115.5 . . ?
C1 C2 C3 115.60(18) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
O2 C3 C4 59.21(13) . . ?
O2 C3 C2 116.32(19) . . ?
C4 C3 C2 121.75(19) . . ?
O2 C3 H3 115.8 . . ?
C4 C3 H3 115.8 . . ?
C2 C3 H3 115.8 . . ?
O2 C4 C3 59.73(13) . . ?
O2 C4 C5 116.89(18) . . ?
C3 C4 C5 122.61(18) . . ?
O2 C4 H4 115.3 . . ?
C3 C4 H4 115.3 . . ?
C5 C4 H4 115.3 . . ?
C4 C5 C6 113.86(17) . . ?
C4 C5 C7 110.00(17) . . ?
C6 C5 C7 109.01(16) . . ?
C4 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C7 C5 H5 107.9 . . ?
O1 C6 C1 59.79(12) . . ?
O1 C6 C5 117.73(16) . . ?
C1 C6 C5 122.54(18) . . ?
O1 C6 H6 115.1 . . ?
C1 C6 H6 115.1 . . ?
C5 C6 H6 115.1 . . ?
C8 C7 C12 118.29(18) . . ?
C8 C7 C5 120.97(18) . . ?
C12 C7 C5 120.74(17) . . ?
C9 C8 C7 120.97(19) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.24(18) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 117.45(18) . . ?
C11 C10 C13 120.52(17) . . ?
C9 C10 C13 122.02(17) . . ?
C12 C11 C10 121.46(18) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 120.59(18) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C10 C13 C14 113.27(17) . . ?
C10 C13 C18 111.98(17) . . ?
C14 C13 C18 109.12(16) . . ?
C10 C13 H13 107.4 . . ?
C14 C13 H13 107.4 . . ?
C18 C13 H13 107.4 . . ?
C15 C14 C13 110.68(17) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 113.15(18) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 110.16(17) . . ?
C15 C16 C19 108.98(18) . . ?
C17 C16 C19 112.75(17) . . ?
C15 C16 H16 108.3 . . ?
C17 C16 H16 108.3 . . ?
C19 C16 H16 108.3 . . ?
C16 C17 C18 112.80(17) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C13 110.99(17) . . ?
C17 C18 H18A 109.4 . . ?
C13 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C13 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C16 116.9(2) . . ?
C20 C19 H19A 108.1 . . ?
C16 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
C16 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 C21 111.4(2) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C1 C2 -112.3(2) . . . . ?
O1 C1 C2 C3 58.3(2) . . . . ?
C6 C1 C2 C3 -10.7(3) . . . . ?
C4 O2 C3 C2 112.9(2) . . . . ?
C1 C2 C3 O2 -58.0(2) . . . . ?
C1 C2 C3 C4 10.6(3) . . . . ?
C3 O2 C4 C5 -113.8(2) . . . . ?
C2 C3 C4 O2 -103.8(2) . . . . ?
O2 C3 C4 C5 104.4(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
O2 C4 C5 C6 58.5(2) . . . . ?
C3 C4 C5 C6 -11.2(3) . . . . ?
O2 C4 C5 C7 -178.83(16) . . . . ?
C3 C4 C5 C7 111.5(2) . . . . ?
C1 O1 C6 C5 113.4(2) . . . . ?
C2 C1 C6 O1 105.3(2) . . . . ?
O1 C1 C6 C5 -105.5(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C4 C5 C6 O1 -59.1(2) . . . . ?
C7 C5 C6 O1 177.63(16) . . . . ?
C4 C5 C6 C1 11.1(3) . . . . ?
C7 C5 C6 C1 -112.2(2) . . . . ?
C4 C5 C7 C8 114.9(2) . . . . ?
C6 C5 C7 C8 -119.6(2) . . . . ?
C4 C5 C7 C12 -65.8(2) . . . . ?
C6 C5 C7 C12 59.7(2) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
C5 C7 C8 C9 178.81(19) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C8 C9 C10 C13 -178.14(19) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C13 C10 C11 C12 178.64(19) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C5 C7 C12 C11 -178.33(18) . . . . ?
C11 C10 C13 C14 136.6(2) . . . . ?
C9 C10 C13 C14 -44.3(3) . . . . ?
C11 C10 C13 C18 -99.5(2) . . . . ?
C9 C10 C13 C18 79.7(2) . . . . ?
C10 C13 C14 C15 -176.28(17) . . . . ?
C18 C13 C14 C15 58.2(2) . . . . ?
C13 C14 C15 C16 -57.0(2) . . . . ?
C14 C15 C16 C17 52.6(2) . . . . ?
C14 C15 C16 C19 176.82(18) . . . . ?
C15 C16 C17 C18 -51.8(3) . . . . ?
C19 C16 C17 C18 -173.79(19) . . . . ?
C16 C17 C18 C13 55.7(2) . . . . ?
C10 C13 C18 C17 175.98(16) . . . . ?
C14 C13 C18 C17 -57.8(2) . . . . ?
C15 C16 C19 C20 173.96(19) . . . . ?
C17 C16 C19 C20 -63.4(3) . . . . ?
C16 C19 C20 C21 177.5(2) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1503425'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-12-15
_audit_creation_method           'by CrystalStructure 4.1'



_chemical_formula_sum            'C23 H28 F8 O6 S2'
_chemical_formula_moiety         'C23 H28 F8 O6 S2'
_chemical_formula_weight         616.58
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.070(3)
_cell_length_b                   15.616(4)
_cell_length_c                   17.611(4)
_cell_angle_alpha                94.940(7)
_cell_angle_beta                 91.272(6)
_cell_angle_gamma                95.758(7)
_cell_volume                     2744.0(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5979
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.28
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272.00
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.353
_diffrn_reflns_number            17265
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.040
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             9191
_reflns_number_gt                3915
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2105
_refine_ls_R_factor_gt           0.0963
_refine_ls_wR_factor_ref         0.2772
_refine_ls_wR_factor_gt          0.2277
_refine_ls_number_restraints     21
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         9191
_refine_ls_number_parameters     705
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1222P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.95
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
S2 S 0.29877(18) 1.03566(13) 0.38005(11) 0.0382(5) Uani 1 1 d . . . . .
S6 S 0.6379(2) 0.63293(17) 0.40692(15) 0.0668(7) Uani 1 1 d . . . . .
S32 S 1.4594(2) 0.79914(15) 0.09867(16) 0.0597(7) Uani 1 1 d . . . . .
S36 S 0.86260(18) 1.02486(13) 0.14261(11) 0.0401(5) Uani 1 1 d . . . . .
F3 F 0.5997(4) 1.0534(3) 0.3423(2) 0.0581(13) Uani 1 1 d . . . . .
F5 F 0.8317(4) 0.8076(3) 0.3691(3) 0.0661(14) Uani 1 1 d . . . . .
F21 F 0.1429(5) 0.9307(3) 0.4536(3) 0.0717(16) Uani 1 1 d . . . . .
F22 F 0.0698(4) 1.0509(3) 0.4369(3) 0.0708(15) Uani 1 1 d . . . . .
F23 F 0.0673(4) 0.9538(4) 0.3432(3) 0.0881(19) Uani 1 1 d . . . . .
F24 F 0.3921(6) 0.5839(4) 0.4426(4) 0.101(2) Uani 1 1 d . . . . .
F25 F 0.5140(6) 0.4823(4) 0.4182(4) 0.106(2) Uani 1 1 d . . . . .
F26 F 0.4404(7) 0.5467(5) 0.3274(4) 0.122(2) Uani 1 1 d . . . . .
F33 F 1.5257(4) 0.9992(3) 0.0861(3) 0.0689(15) Uani 1 1 d . . . . .
F35 F 1.1576(4) 1.1668(3) 0.1011(3) 0.0664(14) Uani 1 1 d . . . . .
F51 F 1.2432(5) 0.6943(4) 0.0728(4) 0.097(2) Uani 1 1 d . . . . .
F52 F 1.4240(5) 0.6341(3) 0.0737(3) 0.0811(16) Uani 1 1 d . . . . .
F53 F 1.3415(7) 0.6845(3) 0.1783(3) 0.105(2) Uani 1 1 d . . . . .
F54 F 0.8879(6) 1.1908(4) 0.1360(4) 0.112(2) Uani 1 1 d . . . . .
F55 F 0.6951(5) 1.1375(4) 0.1626(4) 0.120(3) Uani 1 1 d . . . . .
F56 F 0.8475(7) 1.1524(4) 0.2442(4) 0.122(3) Uani 1 1 d . . . . .
O2 O 0.3551(4) 0.9515(3) 0.3431(2) 0.0320(12) Uani 1 1 d . . . . .
O6 O 0.5880(5) 0.7012(4) 0.3554(3) 0.0482(14) Uani 1 1 d . . . . .
O21 O 0.3672(5) 1.0669(3) 0.4503(3) 0.0463(14) Uani 1 1 d . . . . .
O22 O 0.2776(5) 1.0902(3) 0.3221(3) 0.0558(15) Uani 1 1 d . . . . .
O23 O 0.6569(6) 0.6672(4) 0.4834(4) 0.081(2) Uani 1 1 d . . . . .
O24 O 0.7374(6) 0.5894(4) 0.3682(4) 0.086(2) Uani 1 1 d . . . . .
O32 O 1.3707(5) 0.8626(4) 0.1451(3) 0.0582(15) Uani 1 1 d . . . . .
O36 O 1.0066(5) 1.0338(3) 0.1728(3) 0.0494(14) Uani 1 1 d . . . . .
O51 O 1.4606(7) 0.8122(5) 0.0223(4) 0.101(2) Uani 1 1 d . . . . .
O52 O 1.5738(6) 0.7972(5) 0.1452(5) 0.119(3) Uani 1 1 d . . . . .
O53 O 0.8523(5) 1.0155(3) 0.0625(3) 0.0520(14) Uani 1 1 d . . . . .
O54 O 0.7845(6) 0.9699(4) 0.1869(3) 0.0684(18) Uani 1 1 d . . . . .
C1 C 0.4656(6) 0.8241(5) 0.3593(4) 0.0360(19) Uani 1 1 d . . . . .
H1 H 0.4458 0.8076 0.3037 0.043 Uiso 1 1 calc R U . . .
C2 C 0.4800(6) 0.9228(5) 0.3731(4) 0.0359(19) Uani 1 1 d . . . . .
H2 H 0.4924 0.9411 0.4289 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5939(7) 0.9638(5) 0.3296(4) 0.042(2) Uani 1 1 d . . . . .
H3 H 0.5781 0.9465 0.2739 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7221(7) 0.9331(6) 0.3552(4) 0.050(2) Uani 1 1 d . . . . .
H4A H 0.7970 0.9601 0.3271 0.060 Uiso 1 1 calc R U . . .
H4B H 0.7387 0.9502 0.4103 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7144(6) 0.8372(6) 0.3407(4) 0.048(2) Uani 1 1 d . . . . .
H5 H 0.7045 0.8206 0.2846 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5985(7) 0.7934(5) 0.3805(4) 0.041(2) Uani 1 1 d . . . . .
H6 H 0.6145 0.8023 0.4370 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3519(6) 0.7844(4) 0.4044(4) 0.0294(17) Uani 1 1 d . . . . .
C8 C 0.3553(7) 0.7946(5) 0.4839(4) 0.043(2) Uani 1 1 d . . . . .
H8 H 0.4282 0.8290 0.5100 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2565(7) 0.7563(5) 0.5250(4) 0.040(2) Uani 1 1 d . . . . .
H9 H 0.2643 0.7625 0.5791 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1453(7) 0.7087(5) 0.4900(4) 0.0343(18) Uani 1 1 d . . . . .
C11 C 0.1395(7) 0.7006(5) 0.4121(4) 0.0365(18) Uani 1 1 d . . . . .
H11 H 0.0634 0.6690 0.3867 0.044 Uiso 1 1 calc R U . . .
C12 C 0.2415(6) 0.7372(4) 0.3679(4) 0.0328(18) Uani 1 1 d . . . . .
H12 H 0.2346 0.7296 0.3138 0.039 Uiso 1 1 calc R U . . .
C13 C 0.0367(7) 0.6650(5) 0.5365(4) 0.042(2) Uani 1 1 d . . . . .
H13 H -0.0371 0.6381 0.5006 0.050 Uiso 1 1 calc R U . . .
C14 C -0.0211(8) 0.7297(5) 0.5940(5) 0.053(2) Uani 1 1 d . . . . .
H14A H -0.0696 0.7699 0.5660 0.064 Uiso 1 1 calc R U . . .
H14B H 0.0529 0.7641 0.6242 0.064 Uiso 1 1 calc R U . . .
C15 C -0.1176(7) 0.6839(5) 0.6487(4) 0.052(2) Uani 1 1 d . . . . .
H15A H -0.1458 0.7274 0.6877 0.062 Uiso 1 1 calc R U . . .
H15B H -0.1984 0.6570 0.6194 0.062 Uiso 1 1 calc R U . . .
C16 C -0.0542(7) 0.6151(5) 0.6882(4) 0.047(2) Uani 1 1 d D . . . .
H16 H 0.0258 0.6447 0.7179 0.056 Uiso 1 1 calc R U . . .
C17 C -0.0044(8) 0.5501(5) 0.6309(4) 0.052(2) Uani 1 1 d . . . . .
H17A H -0.0811 0.5187 0.6007 0.063 Uiso 1 1 calc R U . . .
H17B H 0.0404 0.5074 0.6580 0.063 Uiso 1 1 calc R U . . .
C18 C 0.0937(8) 0.5931(5) 0.5771(4) 0.049(2) Uani 1 1 d . . . . .
H18A H 0.1194 0.5485 0.5382 0.058 Uiso 1 1 calc R U . . .
H18B H 0.1756 0.6176 0.6066 0.058 Uiso 1 1 calc R U . . .
C19 C -0.1446(8) 0.5701(6) 0.7455(4) 0.068(3) Uani 1 1 d D . . . .
H19A H -0.2301 0.5470 0.7191 0.081 Uiso 1 1 calc R U . . .
H19B H -0.1013 0.5205 0.7623 0.081 Uiso 1 1 calc R U . . .
C20 C -0.1747(9) 0.6287(6) 0.8164(5) 0.076(3) Uani 1 1 d D . . . .
H20A H -0.0897 0.6565 0.8405 0.091 Uiso 1 1 calc R U . . .
H20B H -0.2271 0.6749 0.8006 0.091 Uiso 1 1 calc R U . . .
C21 C -0.2516(9) 0.5788(7) 0.8735(5) 0.087(3) Uani 1 1 d D . . . .
H21A H -0.1935 0.5408 0.8966 0.104 Uiso 1 1 calc R U . . .
H21B H -0.3286 0.5440 0.8478 0.104 Uiso 1 1 calc R U . . .
H21C H -0.2825 0.6192 0.9133 0.104 Uiso 1 1 calc R U . . .
C22 C 0.1332(8) 0.9876(6) 0.4043(6) 0.054(2) Uani 1 1 d . . . . .
C23 C 0.4863(11) 0.5578(7) 0.3968(7) 0.077(3) Uani 1 1 d . . . . .
C31 C 1.1820(7) 0.9420(5) 0.1487(4) 0.043(2) Uani 1 1 d . . . . .
H31 H 1.2037 0.9536 0.2046 0.052 Uiso 1 1 calc R U . . .
C32 C 1.3140(6) 0.9323(5) 0.1086(4) 0.0379(19) Uani 1 1 d . . . . .
H32 H 1.2964 0.9151 0.0530 0.046 Uiso 1 1 calc R U . . .
C33 C 1.4077(7) 1.0132(5) 0.1194(5) 0.054(2) Uani 1 1 d . . . . .
H33 H 1.4269 1.0259 0.1754 0.065 Uiso 1 1 calc R U . . .
C34 C 1.3472(7) 1.0873(5) 0.0927(4) 0.047(2) Uani 1 1 d . . . . .
H34A H 1.3319 1.0780 0.0368 0.056 Uiso 1 1 calc R U . . .
H34B H 1.4101 1.1401 0.1038 0.056 Uiso 1 1 calc R U . . .
C35 C 1.2162(7) 1.1010(5) 0.1300(5) 0.045(2) Uani 1 1 d . . . . .
H35 H 1.2358 1.1176 0.1855 0.054 Uiso 1 1 calc R U . . .
C36 C 1.1226(6) 1.0209(5) 0.1231(4) 0.0329(18) Uani 1 1 d . . . . .
H36 H 1.0895 1.0085 0.0689 0.039 Uiso 1 1 calc R U . . .
C37 C 1.0852(7) 0.8601(5) 0.1381(5) 0.047(2) Uani 1 1 d . . . . .
C38 C 1.0240(8) 0.8299(5) 0.0677(5) 0.052(2) Uani 1 1 d . . . . .
H38 H 1.0409 0.8614 0.0246 0.063 Uiso 1 1 calc R U . . .
C39 C 0.9384(8) 0.7539(5) 0.0604(4) 0.048(2) Uani 1 1 d . . . . .
H39 H 0.8962 0.7352 0.0122 0.058 Uiso 1 1 calc R U . . .
C40 C 0.9131(7) 0.7049(5) 0.1206(4) 0.042(2) Uani 1 1 d . . . . .
C41 C 0.9781(8) 0.7367(5) 0.1915(4) 0.048(2) Uani 1 1 d . . . . .
H41 H 0.9627 0.7058 0.2351 0.058 Uiso 1 1 calc R U . . .
C42 C 1.0622(7) 0.8109(5) 0.1974(5) 0.044(2) Uani 1 1 d . . . . .
H42 H 1.1067 0.8292 0.2451 0.053 Uiso 1 1 calc R U . . .
C43 C 0.8268(8) 0.6188(5) 0.1114(5) 0.051(2) Uani 1 1 d . . . . .
H43 H 0.7746 0.6154 0.0620 0.061 Uiso 1 1 calc R U . . .
C44 C 0.9139(9) 0.5453(5) 0.1078(6) 0.072(3) Uani 1 1 d . . . . .
H44A H 0.9742 0.5514 0.1536 0.086 Uiso 1 1 calc R U . . .
H44B H 0.9697 0.5477 0.0623 0.086 Uiso 1 1 calc R U . . .
C45 C 0.8285(10) 0.4574(6) 0.1038(7) 0.102(4) Uani 1 1 d . . . . .
H45A H 0.7789 0.4481 0.0541 0.122 Uiso 1 1 calc R U . . .
H45B H 0.8887 0.4112 0.1057 0.122 Uiso 1 1 calc R U . . .
C46 C 0.7326(9) 0.4494(5) 0.1651(7) 0.089(4) Uani 1 1 d D . . . .
H46 H 0.7869 0.4584 0.2139 0.107 Uiso 1 1 calc R U . . .
C47 C 0.6443(8) 0.5215(5) 0.1672(6) 0.069(3) Uani 1 1 d . . . . .
H47A H 0.5834 0.5169 0.2104 0.082 Uiso 1 1 calc R U . . .
H47B H 0.5891 0.5165 0.1195 0.082 Uiso 1 1 calc R U . . .
C48 C 0.7273(7) 0.6090(5) 0.1761(5) 0.055(2) Uani 1 1 d . . . . .
H48A H 0.7770 0.6156 0.2257 0.066 Uiso 1 1 calc R U . . .
H48B H 0.6671 0.6554 0.1761 0.066 Uiso 1 1 calc R U . . .
C49 C 0.6462(13) 0.3621(7) 0.1676(7) 0.136(5) Uani 1 1 d D U . . .
H49A H 0.7010 0.3144 0.1533 0.163 Uiso 1 1 calc R U . . .
H49B H 0.5713 0.3586 0.1298 0.163 Uiso 1 1 calc R U . . .
C50 C 0.5896(14) 0.3507(9) 0.2476(7) 0.138(5) Uani 1 1 d D U . . .
H50A H 0.6661 0.3595 0.2847 0.165 Uiso 1 1 calc R U . . .
H50B H 0.5334 0.3983 0.2597 0.165 Uiso 1 1 calc R U . . .
C51 C 0.5090(18) 0.2680(10) 0.2626(10) 0.210(7) Uani 1 1 d D U . . .
H51A H 0.5692 0.2253 0.2750 0.252 Uiso 1 1 calc R U . . .
H51B H 0.4542 0.2459 0.2171 0.252 Uiso 1 1 calc R U . . .
H51C H 0.4509 0.2789 0.3056 0.252 Uiso 1 1 calc R U . . .
C52 C 1.3602(10) 0.6978(6) 0.1055(6) 0.065(3) Uani 1 1 d . . . . .
C53 C 0.8224(10) 1.1322(6) 0.1721(7) 0.069(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
S2 O22 1.411(5) . ?
S2 O21 1.427(5) . ?
S2 O2 1.579(5) . ?
S2 C22 1.834(8) . ?
S6 O23 1.408(6) . ?
S6 O24 1.420(6) . ?
S6 O6 1.570(5) . ?
S6 C23 1.825(11) . ?
S32 O51 1.378(7) . ?
S32 O52 1.403(7) . ?
S32 O32 1.586(6) . ?
S32 C52 1.800(10) . ?
S36 O54 1.405(5) . ?
S36 O53 1.406(5) . ?
S36 O36 1.522(5) . ?
S36 C53 1.799(9) . ?
F3 C3 1.393(8) . ?
F5 C5 1.408(8) . ?
F21 C22 1.303(10) . ?
F22 C22 1.327(8) . ?
F23 C22 1.295(9) . ?
F24 C23 1.331(10) . ?
F25 C23 1.321(11) . ?
F26 C23 1.288(12) . ?
F33 C33 1.366(8) . ?
F35 C35 1.364(8) . ?
F51 C52 1.294(10) . ?
F52 C52 1.328(9) . ?
F53 C52 1.329(10) . ?
F54 C53 1.296(10) . ?
F55 C53 1.301(10) . ?
F56 C53 1.294(11) . ?
O2 C2 1.478(7) . ?
O6 C6 1.462(9) . ?
O32 C32 1.467(8) . ?
O36 C36 1.495(7) . ?
C1 C6 1.515(9) . ?
C1 C7 1.521(9) . ?
C1 C2 1.531(10) . ?
C1 H1 1.0000 . ?
C2 C3 1.513(9) . ?
C2 H2 1.0000 . ?
C3 C4 1.495(10) . ?
C3 H3 1.0000 . ?
C4 C5 1.490(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.510(9) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C12 1.384(9) . ?
C7 C8 1.394(9) . ?
C8 C9 1.363(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(9) . ?
C10 C13 1.522(9) . ?
C11 C12 1.407(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.533(10) . ?
C13 C18 1.534(10) . ?
C13 H13 1.0000 . ?
C14 C15 1.551(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.514(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.500(10) . ?
C16 C19 1.541(8) . ?
C16 H16 1.0000 . ?
C17 C18 1.531(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.537(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.506(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 C36 1.521(9) . ?
C31 C37 1.523(10) . ?
C31 C32 1.535(9) . ?
C31 H31 1.0000 . ?
C32 C33 1.496(10) . ?
C32 H32 1.0000 . ?
C33 C34 1.468(10) . ?
C33 H33 1.0000 . ?
C34 C35 1.513(10) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.484(10) . ?
C35 H35 1.0000 . ?
C36 H36 1.0000 . ?
C37 C42 1.360(10) . ?
C37 C38 1.395(10) . ?
C38 C39 1.389(10) . ?
C38 H38 0.9500 . ?
C39 C40 1.374(10) . ?
C39 H39 0.9500 . ?
C40 C41 1.423(10) . ?
C40 C43 1.521(10) . ?
C41 C42 1.359(10) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.511(11) . ?
C43 C48 1.542(10) . ?
C43 H43 1.0000 . ?
C44 C45 1.540(12) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.470(12) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.502(11) . ?
C46 C49 1.546(9) . ?
C46 H46 1.0000 . ?
C47 C48 1.521(10) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.548(10) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.502(10) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O22 S2 O21 122.1(4) . . ?
O22 S2 O2 108.6(3) . . ?
O21 S2 O2 111.7(3) . . ?
O22 S2 C22 106.4(4) . . ?
O21 S2 C22 106.7(4) . . ?
O2 S2 C22 98.7(3) . . ?
O23 S6 O24 121.6(4) . . ?
O23 S6 O6 111.3(4) . . ?
O24 S6 O6 109.1(3) . . ?
O23 S6 C23 109.7(5) . . ?
O24 S6 C23 105.6(5) . . ?
O6 S6 C23 96.5(4) . . ?
O51 S32 O52 124.7(5) . . ?
O51 S32 O32 112.0(4) . . ?
O52 S32 O32 105.1(4) . . ?
O51 S32 C52 106.2(5) . . ?
O52 S32 C52 106.0(5) . . ?
O32 S32 C52 100.0(4) . . ?
O54 S36 O53 121.5(4) . . ?
O54 S36 O36 109.0(3) . . ?
O53 S36 O36 112.8(3) . . ?
O54 S36 C53 105.5(4) . . ?
O53 S36 C53 106.7(5) . . ?
O36 S36 C53 98.6(4) . . ?
C2 O2 S2 120.8(4) . . ?
C6 O6 S6 122.2(5) . . ?
C32 O32 S32 120.8(5) . . ?
C36 O36 S36 123.2(4) . . ?
C6 C1 C7 112.2(6) . . ?
C6 C1 C2 107.6(6) . . ?
C7 C1 C2 110.9(5) . . ?
C6 C1 H1 108.7 . . ?
C7 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
O2 C2 C3 107.5(6) . . ?
O2 C2 C1 106.3(5) . . ?
C3 C2 C1 111.9(6) . . ?
O2 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
F3 C3 C4 110.4(6) . . ?
F3 C3 C2 109.4(5) . . ?
C4 C3 C2 109.5(6) . . ?
F3 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C5 C4 C3 109.6(6) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
F5 C5 C4 109.8(6) . . ?
F5 C5 C6 107.3(6) . . ?
C4 C5 C6 111.5(6) . . ?
F5 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
O6 C6 C5 107.8(6) . . ?
O6 C6 C1 106.1(6) . . ?
C5 C6 C1 113.1(6) . . ?
O6 C6 H6 109.9 . . ?
C5 C6 H6 109.9 . . ?
C1 C6 H6 109.9 . . ?
C12 C7 C8 117.9(6) . . ?
C12 C7 C1 121.0(6) . . ?
C8 C7 C1 121.1(6) . . ?
C9 C8 C7 121.5(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.7(7) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 117.0(6) . . ?
C11 C10 C13 121.7(7) . . ?
C9 C10 C13 121.2(6) . . ?
C10 C11 C12 122.7(7) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C7 C12 C11 119.1(6) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C10 C13 C14 111.9(6) . . ?
C10 C13 C18 109.2(5) . . ?
C14 C13 C18 110.9(6) . . ?
C10 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C18 C13 H13 108.3 . . ?
C13 C14 C15 112.0(6) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 112.3(6) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 110.7(6) . . ?
C17 C16 C19 110.9(6) . . ?
C15 C16 C19 114.2(6) . . ?
C17 C16 H16 106.9 . . ?
C15 C16 H16 106.9 . . ?
C19 C16 H16 106.9 . . ?
C16 C17 C18 111.6(6) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 C13 113.3(6) . . ?
C17 C18 H18A 108.9 . . ?
C13 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C13 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C16 114.5(7) . . ?
C20 C19 H19A 108.6 . . ?
C16 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C16 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C19 111.7(7) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F23 C22 F21 111.3(8) . . ?
F23 C22 F22 109.4(7) . . ?
F21 C22 F22 107.8(7) . . ?
F23 C22 S2 110.2(6) . . ?
F21 C22 S2 111.0(6) . . ?
F22 C22 S2 107.0(6) . . ?
F26 C23 F25 108.6(10) . . ?
F26 C23 F24 109.7(10) . . ?
F25 C23 F24 106.3(8) . . ?
F26 C23 S6 111.9(7) . . ?
F25 C23 S6 108.8(8) . . ?
F24 C23 S6 111.4(8) . . ?
C36 C31 C37 113.1(6) . . ?
C36 C31 C32 109.1(6) . . ?
C37 C31 C32 112.7(6) . . ?
C36 C31 H31 107.2 . . ?
C37 C31 H31 107.2 . . ?
C32 C31 H31 107.2 . . ?
O32 C32 C33 110.0(6) . . ?
O32 C32 C31 104.3(5) . . ?
C33 C32 C31 112.1(6) . . ?
O32 C32 H32 110.1 . . ?
C33 C32 H32 110.1 . . ?
C31 C32 H32 110.1 . . ?
F33 C33 C34 113.5(6) . . ?
F33 C33 C32 109.4(7) . . ?
C34 C33 C32 111.7(6) . . ?
F33 C33 H33 107.4 . . ?
C34 C33 H33 107.4 . . ?
C32 C33 H33 107.4 . . ?
C33 C34 C35 112.4(6) . . ?
C33 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
F35 C35 C36 110.2(6) . . ?
F35 C35 C34 111.6(6) . . ?
C36 C35 C34 111.8(6) . . ?
F35 C35 H35 107.7 . . ?
C36 C35 H35 107.7 . . ?
C34 C35 H35 107.7 . . ?
C35 C36 O36 109.1(6) . . ?
C35 C36 C31 114.3(6) . . ?
O36 C36 C31 105.9(5) . . ?
C35 C36 H36 109.1 . . ?
O36 C36 H36 109.1 . . ?
C31 C36 H36 109.1 . . ?
C42 C37 C38 117.7(8) . . ?
C42 C37 C31 119.8(7) . . ?
C38 C37 C31 122.4(8) . . ?
C39 C38 C37 120.4(7) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C40 C39 C38 122.0(8) . . ?
C40 C39 H39 119.0 . . ?
C38 C39 H39 119.0 . . ?
C39 C40 C41 116.4(8) . . ?
C39 C40 C43 122.0(7) . . ?
C41 C40 C43 121.5(7) . . ?
C42 C41 C40 120.7(7) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C37 122.8(8) . . ?
C41 C42 H42 118.6 . . ?
C37 C42 H42 118.6 . . ?
C44 C43 C40 110.1(6) . . ?
C44 C43 C48 109.8(6) . . ?
C40 C43 C48 112.3(6) . . ?
C44 C43 H43 108.2 . . ?
C40 C43 H43 108.2 . . ?
C48 C43 H43 108.2 . . ?
C43 C44 C45 111.0(7) . . ?
C43 C44 H44A 109.4 . . ?
C45 C44 H44A 109.4 . . ?
C43 C44 H44B 109.4 . . ?
C45 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?
C46 C45 C44 114.2(8) . . ?
C46 C45 H45A 108.7 . . ?
C44 C45 H45A 108.7 . . ?
C46 C45 H45B 108.7 . . ?
C44 C45 H45B 108.7 . . ?
H45A C45 H45B 107.6 . . ?
C45 C46 C47 110.5(8) . . ?
C45 C46 C49 117.9(9) . . ?
C47 C46 C49 109.7(8) . . ?
C45 C46 H46 106.0 . . ?
C47 C46 H46 106.0 . . ?
C49 C46 H46 106.0 . . ?
C46 C47 C48 110.8(7) . . ?
C46 C47 H47A 109.5 . . ?
C48 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
C48 C47 H47B 109.5 . . ?
H47A C47 H47B 108.1 . . ?
C47 C48 C43 111.7(7) . . ?
C47 C48 H48A 109.3 . . ?
C43 C48 H48A 109.3 . . ?
C47 C48 H48B 109.3 . . ?
C43 C48 H48B 109.3 . . ?
H48A C48 H48B 107.9 . . ?
C46 C49 C50 112.1(10) . . ?
C46 C49 H49A 109.2 . . ?
C50 C49 H49A 109.2 . . ?
C46 C49 H49B 109.2 . . ?
C50 C49 H49B 109.2 . . ?
H49A C49 H49B 107.9 . . ?
C51 C50 C49 120.1(12) . . ?
C51 C50 H50A 107.3 . . ?
C49 C50 H50A 107.3 . . ?
C51 C50 H50B 107.3 . . ?
C49 C50 H50B 107.3 . . ?
H50A C50 H50B 106.9 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
F51 C52 F52 108.8(8) . . ?
F51 C52 F53 107.0(8) . . ?
F52 C52 F53 108.5(8) . . ?
F51 C52 S32 113.1(7) . . ?
F52 C52 S32 109.2(6) . . ?
F53 C52 S32 110.2(7) . . ?
F56 C53 F54 107.2(9) . . ?
F56 C53 F55 105.2(8) . . ?
F54 C53 F55 109.0(9) . . ?
F56 C53 S36 111.9(8) . . ?
F54 C53 S36 112.7(7) . . ?
F55 C53 S36 110.6(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O22 S2 O2 C2 126.6(5) . . . . ?
O21 S2 O2 C2 -10.9(5) . . . . ?
C22 S2 O2 C2 -122.8(5) . . . . ?
O23 S6 O6 C6 16.3(6) . . . . ?
O24 S6 O6 C6 -120.6(5) . . . . ?
C23 S6 O6 C6 130.4(6) . . . . ?
O51 S32 O32 C32 -7.0(7) . . . . ?
O52 S32 O32 C32 131.1(6) . . . . ?
C52 S32 O32 C32 -119.1(6) . . . . ?
O54 S36 O36 C36 129.6(5) . . . . ?
O53 S36 O36 C36 -8.5(6) . . . . ?
C53 S36 O36 C36 -120.7(6) . . . . ?
S2 O2 C2 C3 -90.9(6) . . . . ?
S2 O2 C2 C1 149.1(4) . . . . ?
C6 C1 C2 O2 173.2(5) . . . . ?
C7 C1 C2 O2 -63.8(7) . . . . ?
C6 C1 C2 C3 56.1(7) . . . . ?
C7 C1 C2 C3 179.2(6) . . . . ?
O2 C2 C3 F3 61.8(7) . . . . ?
C1 C2 C3 F3 178.1(5) . . . . ?
O2 C2 C3 C4 -177.1(6) . . . . ?
C1 C2 C3 C4 -60.8(8) . . . . ?
F3 C3 C4 C5 -179.7(5) . . . . ?
C2 C3 C4 C5 59.8(8) . . . . ?
C3 C4 C5 F5 -176.3(5) . . . . ?
C3 C4 C5 C6 -57.5(8) . . . . ?
S6 O6 C6 C5 103.1(6) . . . . ?
S6 O6 C6 C1 -135.5(5) . . . . ?
F5 C5 C6 O6 -67.0(7) . . . . ?
C4 C5 C6 O6 172.8(6) . . . . ?
F5 C5 C6 C1 176.0(6) . . . . ?
C4 C5 C6 C1 55.8(9) . . . . ?
C7 C1 C6 O6 66.5(7) . . . . ?
C2 C1 C6 O6 -171.3(5) . . . . ?
C7 C1 C6 C5 -175.6(6) . . . . ?
C2 C1 C6 C5 -53.3(8) . . . . ?
C6 C1 C7 C12 -122.5(7) . . . . ?
C2 C1 C7 C12 117.1(7) . . . . ?
C6 C1 C7 C8 57.6(9) . . . . ?
C2 C1 C7 C8 -62.7(8) . . . . ?
C12 C7 C8 C9 2.9(11) . . . . ?
C1 C7 C8 C9 -177.3(7) . . . . ?
C7 C8 C9 C10 -2.9(12) . . . . ?
C8 C9 C10 C11 0.9(11) . . . . ?
C8 C9 C10 C13 179.0(7) . . . . ?
C9 C10 C11 C12 1.0(11) . . . . ?
C13 C10 C11 C12 -177.1(6) . . . . ?
C8 C7 C12 C11 -1.0(10) . . . . ?
C1 C7 C12 C11 179.1(6) . . . . ?
C10 C11 C12 C7 -0.9(10) . . . . ?
C11 C10 C13 C14 -125.4(8) . . . . ?
C9 C10 C13 C14 56.6(9) . . . . ?
C11 C10 C13 C18 111.4(8) . . . . ?
C9 C10 C13 C18 -66.5(9) . . . . ?
C10 C13 C14 C15 -172.3(7) . . . . ?
C18 C13 C14 C15 -50.1(9) . . . . ?
C13 C14 C15 C16 53.6(9) . . . . ?
C14 C15 C16 C17 -56.2(9) . . . . ?
C14 C15 C16 C19 177.8(7) . . . . ?
C15 C16 C17 C18 56.3(9) . . . . ?
C19 C16 C17 C18 -175.9(7) . . . . ?
C16 C17 C18 C13 -54.9(9) . . . . ?
C10 C13 C18 C17 175.0(6) . . . . ?
C14 C13 C18 C17 51.3(9) . . . . ?
C17 C16 C19 C20 166.9(8) . . . . ?
C15 C16 C19 C20 -67.2(10) . . . . ?
C16 C19 C20 C21 -174.2(8) . . . . ?
O22 S2 C22 F23 51.4(7) . . . . ?
O21 S2 C22 F23 -176.9(6) . . . . ?
O2 S2 C22 F23 -61.0(7) . . . . ?
O22 S2 C22 F21 175.1(6) . . . . ?
O21 S2 C22 F21 -53.2(7) . . . . ?
O2 S2 C22 F21 62.7(6) . . . . ?
O22 S2 C22 F22 -67.5(7) . . . . ?
O21 S2 C22 F22 64.2(7) . . . . ?
O2 S2 C22 F22 -179.9(6) . . . . ?
O23 S6 C23 F26 158.7(8) . . . . ?
O24 S6 C23 F26 -68.7(9) . . . . ?
O6 S6 C23 F26 43.3(8) . . . . ?
O23 S6 C23 F25 -81.3(8) . . . . ?
O24 S6 C23 F25 51.3(9) . . . . ?
O6 S6 C23 F25 163.2(7) . . . . ?
O23 S6 C23 F24 35.5(9) . . . . ?
O24 S6 C23 F24 168.1(7) . . . . ?
O6 S6 C23 F24 -80.0(8) . . . . ?
S32 O32 C32 C33 -91.5(7) . . . . ?
S32 O32 C32 C31 148.1(5) . . . . ?
C36 C31 C32 O32 172.4(6) . . . . ?
C37 C31 C32 O32 -61.1(8) . . . . ?
C36 C31 C32 C33 53.4(8) . . . . ?
C37 C31 C32 C33 179.9(7) . . . . ?
O32 C32 C33 F33 61.2(8) . . . . ?
C31 C32 C33 F33 176.7(6) . . . . ?
O32 C32 C33 C34 -172.4(6) . . . . ?
C31 C32 C33 C34 -56.9(9) . . . . ?
F33 C33 C34 C35 179.5(6) . . . . ?
C32 C33 C34 C35 55.4(10) . . . . ?
C33 C34 C35 F35 -176.3(7) . . . . ?
C33 C34 C35 C36 -52.3(9) . . . . ?
F35 C35 C36 O36 -65.7(7) . . . . ?
C34 C35 C36 O36 169.5(6) . . . . ?
F35 C35 C36 C31 176.0(6) . . . . ?
C34 C35 C36 C31 51.2(8) . . . . ?
S36 O36 C36 C35 121.5(6) . . . . ?
S36 O36 C36 C31 -115.1(6) . . . . ?
C37 C31 C36 C35 -177.8(6) . . . . ?
C32 C31 C36 C35 -51.5(8) . . . . ?
C37 C31 C36 O36 62.1(8) . . . . ?
C32 C31 C36 O36 -171.7(5) . . . . ?
C36 C31 C37 C42 -128.3(7) . . . . ?
C32 C31 C37 C42 107.4(8) . . . . ?
C36 C31 C37 C38 55.6(9) . . . . ?
C32 C31 C37 C38 -68.7(9) . . . . ?
C42 C37 C38 C39 2.6(11) . . . . ?
C31 C37 C38 C39 178.7(7) . . . . ?
C37 C38 C39 C40 -1.5(12) . . . . ?
C38 C39 C40 C41 0.7(11) . . . . ?
C38 C39 C40 C43 -175.8(7) . . . . ?
C39 C40 C41 C42 -1.1(11) . . . . ?
C43 C40 C41 C42 175.4(7) . . . . ?
C40 C41 C42 C37 2.4(12) . . . . ?
C38 C37 C42 C41 -3.1(12) . . . . ?
C31 C37 C42 C41 -179.3(7) . . . . ?
C39 C40 C43 C44 101.4(9) . . . . ?
C41 C40 C43 C44 -75.0(9) . . . . ?
C39 C40 C43 C48 -135.9(7) . . . . ?
C41 C40 C43 C48 47.7(10) . . . . ?
C40 C43 C44 C45 176.3(8) . . . . ?
C48 C43 C44 C45 52.1(10) . . . . ?
C43 C44 C45 C46 -53.9(12) . . . . ?
C44 C45 C46 C47 55.1(13) . . . . ?
C44 C45 C46 C49 -177.6(10) . . . . ?
C45 C46 C47 C48 -56.3(12) . . . . ?
C49 C46 C47 C48 172.0(9) . . . . ?
C46 C47 C48 C43 57.6(10) . . . . ?
C44 C43 C48 C47 -55.6(9) . . . . ?
C40 C43 C48 C47 -178.5(7) . . . . ?
C45 C46 C49 C50 159.4(11) . . . . ?
C47 C46 C49 C50 -73.0(13) . . . . ?
C46 C49 C50 C51 -176.8(13) . . . . ?
O51 S32 C52 F51 -53.5(8) . . . . ?
O52 S32 C52 F51 172.0(7) . . . . ?
O32 S32 C52 F51 63.1(8) . . . . ?
O51 S32 C52 F52 67.7(8) . . . . ?
O52 S32 C52 F52 -66.8(8) . . . . ?
O32 S32 C52 F52 -175.7(6) . . . . ?
O51 S32 C52 F53 -173.2(6) . . . . ?
O52 S32 C52 F53 52.3(8) . . . . ?
O32 S32 C52 F53 -56.7(7) . . . . ?
O54 S36 C53 F56 59.0(8) . . . . ?
O53 S36 C53 F56 -170.6(7) . . . . ?
O36 S36 C53 F56 -53.6(8) . . . . ?
O54 S36 C53 F54 179.8(8) . . . . ?
O53 S36 C53 F54 -49.8(9) . . . . ?
O36 S36 C53 F54 67.3(9) . . . . ?
O54 S36 C53 F55 -58.0(9) . . . . ?
O53 S36 C53 F55 72.5(8) . . . . ?
O36 S36 C53 F55 -170.5(8) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1503426'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-01
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H28 F8 O6 S2'
_chemical_formula_moiety         'C23 H28 F8 O6 S2'
_chemical_formula_weight         616.58
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        C2/c
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   44.560(17)
_cell_length_b                   5.5896(15)
_cell_length_c                   26.277(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 124.357(7)
_cell_angle_gamma                90.0000
_cell_volume                     5403(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5162
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2544.00
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_T_max  0.994

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            16828
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_theta_max         25.363
_diffrn_reflns_theta_min         1.933
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4913
_reflns_number_gt                2521
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1275
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4913
_refine_ls_number_parameters     353
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0469P)²+6.6592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16515(3) 1.2015(2) 1.10124(6) 0.0463(4) Uani 1 1 d . . . . .
S2 S 0.19661(3) 1.0852(2) 0.85371(5) 0.0463(4) Uani 1 1 d . . . . .
F1 F 0.14676(7) 0.6096(4) 0.96489(11) 0.0520(7) Uani 1 1 d . . . . .
F2 F 0.24468(6) 0.9942(4) 0.99777(11) 0.0467(7) Uani 1 1 d . . . . .
F3 F 0.22951(10) 1.3582(9) 1.18092(16) 0.1243(16) Uani 1 1 d . . . . .
F4 F 0.22240(12) 0.9814(9) 1.18620(16) 0.149(2) Uani 1 1 d . . . . .
F5 F 0.20102(10) 1.2348(7) 1.21953(14) 0.1052(13) Uani 1 1 d . . . . .
F6 F 0.14933(9) 1.4096(6) 0.78193(13) 0.0849(10) Uani 1 1 d . . . . .
F7 F 0.13171(9) 1.0514(6) 0.75427(13) 0.0903(11) Uani 1 1 d . . . . .
F8 F 0.17074(9) 1.2013(6) 0.74182(13) 0.0821(10) Uani 1 1 d . . . . .
O1 O 0.17904(8) 1.1401(5) 1.06003(13) 0.0412(8) Uani 1 1 d . . . . .
O2 O 0.15449(10) 1.4447(5) 1.09055(16) 0.0668(10) Uani 1 1 d . . . . .
O3 O 0.14240(9) 1.0199(6) 1.09887(16) 0.0669(10) Uani 1 1 d . . . . .
O4 O 0.17957(7) 1.1479(5) 0.89027(12) 0.0401(8) Uani 1 1 d . . . . .
O5 O 0.19915(9) 0.8329(6) 0.84947(14) 0.0568(9) Uani 1 1 d . . . . .
O6 O 0.22632(8) 1.2384(6) 0.87230(15) 0.0656(10) Uani 1 1 d . . . . .
C1 C 0.18051(12) 0.8869(7) 1.04272(19) 0.0394(11) Uani 1 1 d . . . . .
H1 H 0.1808 0.7728 1.0723 0.047 Uiso 1 1 calc R U . . .
C2 C 0.14633(12) 0.8526(7) 0.9783(2) 0.0420(11) Uani 1 1 d . . . . .
H2 H 0.1244 0.8862 0.9787 0.050 Uiso 1 1 calc R U . . .
C3 C 0.14526(11) 1.0067(7) 0.92942(18) 0.0348(10) Uani 1 1 d . . . . .
H3 H 0.1447 1.1771 0.9404 0.042 Uiso 1 1 calc R U . . .
C4 C 0.18069(11) 0.9735(7) 0.93341(19) 0.0383(11) Uani 1 1 d . . . . .
H4 H 0.1823 0.8069 0.9213 0.046 Uiso 1 1 calc R U . . .
C5 C 0.21339(11) 1.0285(8) 0.99770(19) 0.0403(11) Uani 1 1 d . . . . .
H5 H 0.2122 1.1986 1.0083 0.048 Uiso 1 1 calc R U . . .
C6 C 0.21484(11) 0.8642(8) 1.04489(19) 0.0413(11) Uani 1 1 d . . . . .
H6A H 0.2178 0.6966 1.0363 0.050 Uiso 1 1 calc R U . . .
H6B H 0.2360 0.9063 1.0866 0.050 Uiso 1 1 calc R U . . .
C7 C 0.11140(11) 0.9671(7) 0.86565(19) 0.0367(11) Uani 1 1 d . . . . .
C8 C 0.08374(12) 1.1342(8) 0.8400(2) 0.0421(12) Uani 1 1 d . . . . .
H8 H 0.0863 1.2736 0.8628 0.050 Uiso 1 1 calc R U . . .
C9 C 0.05235(12) 1.1020(8) 0.7817(2) 0.0432(12) Uani 1 1 d . . . . .
H9 H 0.0337 1.2193 0.7656 0.052 Uiso 1 1 calc R U . . .
C10 C 0.04744(11) 0.9030(8) 0.74637(19) 0.0372(11) Uani 1 1 d . . . . .
C11 C 0.07530(11) 0.7347(8) 0.7725(2) 0.0441(12) Uani 1 1 d . . . . .
H11 H 0.0727 0.5956 0.7496 0.053 Uiso 1 1 calc R U . . .
C12 C 0.10664(12) 0.7646(8) 0.8308(2) 0.0434(12) Uani 1 1 d . . . . .
H12 H 0.1251 0.6459 0.8474 0.052 Uiso 1 1 calc R U . . .
C13 C 0.01371(12) 0.8766(8) 0.68115(19) 0.0413(11) Uani 1 1 d . . . . .
H13 H -0.0041 1.0000 0.6758 0.050 Uiso 1 1 calc R U . . .
C14 C -0.00467(12) 0.6354(9) 0.6689(2) 0.0525(13) Uani 1 1 d . . . . .
H14A H -0.0119 0.6113 0.6979 0.063 Uiso 1 1 calc R U . . .
H14B H 0.0128 0.5079 0.6765 0.063 Uiso 1 1 calc R U . . .
C15 C -0.03800(12) 0.6142(9) 0.6034(2) 0.0548(14) Uani 1 1 d . . . . .
H15A H -0.0485 0.4522 0.5973 0.066 Uiso 1 1 calc R U . . .
H15B H -0.0564 0.7315 0.5971 0.066 Uiso 1 1 calc R U . . .
C16 C -0.02976(12) 0.6565(9) 0.5564(2) 0.0524(13) Uani 1 1 d . . . . .
H16 H -0.0114 0.5340 0.5635 0.063 Uiso 1 1 calc R U . . .
C17 C -0.01169(14) 0.9018(10) 0.5681(2) 0.0673(16) Uani 1 1 d . . . . .
H17A H -0.0047 0.9257 0.5387 0.081 Uiso 1 1 calc R U . . .
H17B H -0.0295 1.0277 0.5601 0.081 Uiso 1 1 calc R U . . .
C18 C 0.02207(13) 0.9296(10) 0.6339(2) 0.0606(15) Uani 1 1 d . . . . .
H18A H 0.0413 0.8192 0.6402 0.073 Uiso 1 1 calc R U . . .
H18B H 0.0314 1.0950 0.6398 0.073 Uiso 1 1 calc R U . . .
C19 C -0.06299(13) 0.6238(11) 0.4902(2) 0.0692(16) Uani 1 1 d . . . . .
H19A H -0.0756 0.4753 0.4885 0.083 Uiso 1 1 calc R U . . .
H19B H -0.0799 0.7586 0.4803 0.083 Uiso 1 1 calc R U . . .
C20 C -0.05600(15) 0.6106(14) 0.4425(2) 0.098(2) Uani 1 1 d . . . . .
H20A H -0.0374 0.4860 0.4542 0.118 Uiso 1 1 calc R U . . .
H20B H -0.0456 0.7654 0.4411 0.118 Uiso 1 1 calc R U . . .
C21 C -0.08867(14) 0.5554(12) 0.3786(2) 0.087(2) Uani 1 1 d . . . . .
H21A H -0.1084 0.6666 0.3681 0.104 Uiso 1 1 calc R U . . .
H21B H -0.0967 0.3910 0.3774 0.104 Uiso 1 1 calc R U . . .
H21C H -0.0822 0.5729 0.3488 0.104 Uiso 1 1 calc R U . . .
C22 C 0.20744(19) 1.1884(13) 1.1774(3) 0.0803(18) Uani 1 1 d . . . . .
C23 C 0.15954(14) 1.1925(9) 0.7786(2) 0.0536(13) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.411(3) . ?
S1 O2 1.415(3) . ?
S1 O1 1.559(3) . ?
S1 C22 1.818(6) . ?
S2 O6 1.412(3) . ?
S2 O5 1.424(3) . ?
S2 O4 1.564(3) . ?
S2 C23 1.818(5) . ?
F1 C2 1.406(5) . ?
F2 C5 1.407(5) . ?
F3 C22 1.332(7) . ?
F4 C22 1.290(7) . ?
F5 C22 1.315(6) . ?
F6 C23 1.316(5) . ?
F7 C23 1.293(5) . ?
F8 C23 1.316(5) . ?
O1 C1 1.499(5) . ?
O4 C4 1.474(5) . ?
C1 C6 1.503(6) . ?
C1 C2 1.520(6) . ?
C1 H1 1.0000 . ?
C2 C3 1.525(6) . ?
C2 H2 1.0000 . ?
C3 C7 1.510(5) . ?
C3 C4 1.533(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.514(6) . ?
C4 H4 1.0000 . ?
C5 C6 1.515(6) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.381(6) . ?
C7 C12 1.394(6) . ?
C8 C9 1.385(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(6) . ?
C10 C13 1.520(6) . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.513(6) . ?
C13 C14 1.515(6) . ?
C13 H13 1.0000 . ?
C14 C15 1.516(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.491(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.531(7) . ?
C16 C19 1.531(6) . ?
C16 H16 1.0000 . ?
C17 C18 1.531(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.456(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.508(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 122.0(2) . . ?
O3 S1 O1 111.59(19) . . ?
O2 S1 O1 107.11(18) . . ?
O3 S1 C22 107.0(3) . . ?
O2 S1 C22 106.3(3) . . ?
O1 S1 C22 100.7(3) . . ?
O6 S2 O5 121.8(2) . . ?
O6 S2 O4 109.71(19) . . ?
O5 S2 O4 110.94(18) . . ?
O6 S2 C23 106.0(2) . . ?
O5 S2 C23 107.8(2) . . ?
O4 S2 C23 97.7(2) . . ?
C1 O1 S1 121.4(2) . . ?
C4 O4 S2 120.4(3) . . ?
O1 C1 C6 106.6(3) . . ?
O1 C1 C2 105.6(3) . . ?
C6 C1 C2 113.0(4) . . ?
O1 C1 H1 110.5 . . ?
C6 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
F1 C2 C1 104.7(3) . . ?
F1 C2 C3 109.4(3) . . ?
C1 C2 C3 113.7(4) . . ?
F1 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C7 C3 C2 112.9(3) . . ?
C7 C3 C4 113.8(3) . . ?
C2 C3 C4 109.4(3) . . ?
C7 C3 H3 106.8 . . ?
C2 C3 H3 106.8 . . ?
C4 C3 H3 106.8 . . ?
O4 C4 C5 108.5(3) . . ?
O4 C4 C3 106.3(3) . . ?
C5 C4 C3 110.9(4) . . ?
O4 C4 H4 110.4 . . ?
C5 C4 H4 110.4 . . ?
C3 C4 H4 110.4 . . ?
F2 C5 C4 107.6(3) . . ?
F2 C5 C6 109.4(3) . . ?
C4 C5 C6 111.1(4) . . ?
F2 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
C1 C6 C5 110.2(4) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C12 117.8(4) . . ?
C8 C7 C3 120.0(4) . . ?
C12 C7 C3 122.3(4) . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C11 116.9(4) . . ?
C9 C10 C13 121.0(4) . . ?
C11 C10 C13 122.0(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 120.7(4) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C18 C13 C14 110.7(4) . . ?
C18 C13 C10 111.2(4) . . ?
C14 C13 C10 113.5(4) . . ?
C18 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C10 C13 H13 107.0 . . ?
C13 C14 C15 112.2(4) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 112.7(4) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 108.9(4) . . ?
C15 C16 C19 112.9(4) . . ?
C17 C16 C19 113.3(4) . . ?
C15 C16 H16 107.1 . . ?
C17 C16 H16 107.1 . . ?
C19 C16 H16 107.1 . . ?
C18 C17 C16 112.8(4) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C13 C18 C17 111.6(4) . . ?
C13 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C13 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C16 116.4(4) . . ?
C20 C19 H19A 108.2 . . ?
C16 C19 H19A 108.2 . . ?
C20 C19 H19B 108.2 . . ?
C16 C19 H19B 108.2 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 C21 115.3(5) . . ?
C19 C20 H20A 108.4 . . ?
C21 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
C21 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F4 C22 F5 111.3(6) . . ?
F4 C22 F3 109.8(6) . . ?
F5 C22 F3 107.7(5) . . ?
F4 C22 S1 110.0(4) . . ?
F5 C22 S1 109.7(5) . . ?
F3 C22 S1 108.2(5) . . ?
F7 C23 F8 108.4(4) . . ?
F7 C23 F6 108.9(5) . . ?
F8 C23 F6 107.6(4) . . ?
F7 C23 S2 111.5(4) . . ?
F8 C23 S2 108.7(4) . . ?
F6 C23 S2 111.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 O1 C1 -22.9(3) . . . . ?
O2 S1 O1 C1 -158.8(3) . . . . ?
C22 S1 O1 C1 90.3(4) . . . . ?
O6 S2 O4 C4 -115.2(3) . . . . ?
O5 S2 O4 C4 22.2(3) . . . . ?
C23 S2 O4 C4 134.7(3) . . . . ?
S1 O1 C1 C6 -141.2(3) . . . . ?
S1 O1 C1 C2 98.4(3) . . . . ?
O1 C1 C2 F1 -175.5(3) . . . . ?
C6 C1 C2 F1 68.3(4) . . . . ?
O1 C1 C2 C3 65.1(4) . . . . ?
C6 C1 C2 C3 -51.1(5) . . . . ?
F1 C2 C3 C7 62.4(4) . . . . ?
C1 C2 C3 C7 179.1(3) . . . . ?
F1 C2 C3 C4 -65.4(4) . . . . ?
C1 C2 C3 C4 51.2(5) . . . . ?
S2 O4 C4 C5 95.3(4) . . . . ?
S2 O4 C4 C3 -145.4(3) . . . . ?
C7 C3 C4 O4 59.3(4) . . . . ?
C2 C3 C4 O4 -173.4(3) . . . . ?
C7 C3 C4 C5 177.0(3) . . . . ?
C2 C3 C4 C5 -55.7(4) . . . . ?
O4 C4 C5 F2 -63.6(4) . . . . ?
C3 C4 C5 F2 180.0(3) . . . . ?
O4 C4 C5 C6 176.7(3) . . . . ?
C3 C4 C5 C6 60.3(5) . . . . ?
O1 C1 C6 C5 -62.8(4) . . . . ?
C2 C1 C6 C5 52.8(5) . . . . ?
F2 C5 C6 C1 -176.4(3) . . . . ?
C4 C5 C6 C1 -57.8(5) . . . . ?
C2 C3 C7 C8 104.0(5) . . . . ?
C4 C3 C7 C8 -130.5(4) . . . . ?
C2 C3 C7 C12 -75.7(5) . . . . ?
C4 C3 C7 C12 49.8(5) . . . . ?
C12 C7 C8 C9 -0.1(7) . . . . ?
C3 C7 C8 C9 -179.8(4) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C8 C9 C10 C13 -176.7(4) . . . . ?
C9 C10 C11 C12 -0.5(7) . . . . ?
C13 C10 C11 C12 177.2(4) . . . . ?
C10 C11 C12 C7 -0.3(7) . . . . ?
C8 C7 C12 C11 0.5(7) . . . . ?
C3 C7 C12 C11 -179.8(4) . . . . ?
C9 C10 C13 C18 103.6(5) . . . . ?
C11 C10 C13 C18 -73.9(5) . . . . ?
C9 C10 C13 C14 -130.8(4) . . . . ?
C11 C10 C13 C14 51.6(6) . . . . ?
C18 C13 C14 C15 -53.8(5) . . . . ?
C10 C13 C14 C15 -179.6(4) . . . . ?
C13 C14 C15 C16 56.9(6) . . . . ?
C14 C15 C16 C17 -55.9(5) . . . . ?
C14 C15 C16 C19 177.3(4) . . . . ?
C15 C16 C17 C18 55.0(6) . . . . ?
C19 C16 C17 C18 -178.5(4) . . . . ?
C14 C13 C18 C17 52.5(6) . . . . ?
C10 C13 C18 C17 179.6(4) . . . . ?
C16 C17 C18 C13 -54.4(6) . . . . ?
C15 C16 C19 C20 -167.2(5) . . . . ?
C17 C16 C19 C20 68.4(7) . . . . ?
C16 C19 C20 C21 174.5(5) . . . . ?
O3 S1 C22 F4 59.8(6) . . . . ?
O2 S1 C22 F4 -168.4(5) . . . . ?
O1 S1 C22 F4 -56.8(6) . . . . ?
O3 S1 C22 F5 -62.8(5) . . . . ?
O2 S1 C22 F5 69.0(5) . . . . ?
O1 S1 C22 F5 -179.5(4) . . . . ?
O3 S1 C22 F3 179.9(4) . . . . ?
O2 S1 C22 F3 -48.3(5) . . . . ?
O1 S1 C22 F3 63.2(5) . . . . ?
O6 S2 C23 F7 174.0(4) . . . . ?
O5 S2 C23 F7 42.1(4) . . . . ?
O4 S2 C23 F7 -72.9(4) . . . . ?
O6 S2 C23 F8 54.6(4) . . . . ?
O5 S2 C23 F8 -77.3(4) . . . . ?
O4 S2 C23 F8 167.7(3) . . . . ?
O6 S2 C23 F6 -64.0(4) . . . . ?
O5 S2 C23 F6 164.1(4) . . . . ?
O4 S2 C23 F6 49.1(4) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/petroleum ether'
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1503427'
_audit_update_record             
;
2016-09-08 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-01
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H27 F5 O3 S'
_chemical_formula_moiety         'C22 H27 F5 O3 S'
_chemical_formula_weight         466.51
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.4268(8)
_cell_length_b                   10.7827(15)
_cell_length_c                   19.506(3)
_cell_angle_alpha                78.369(6)
_cell_angle_beta                 82.270(7)
_cell_angle_gamma                79.893(6)
_cell_volume                     1094.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3004
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488.00
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_T_max  0.996

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            21593
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_theta_max         25.327
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3957
_reflns_number_gt                3437
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1159
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3957
_refine_ls_number_parameters     281
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0907P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.72761(8) 0.52670(4) 0.30353(2) 0.02215(16) Uani 1 1 d . . . . .
F1 F 0.77118(18) 0.51679(9) 0.46836(5) 0.0249(3) Uani 1 1 d . . . . .
F2 F 0.35914(18) 0.17278(10) 0.49833(5) 0.0254(3) Uani 1 1 d . . . . .
F3 F 1.0725(2) 0.45405(11) 0.20625(6) 0.0408(3) Uani 1 1 d . . . . .
F4 F 0.7520(2) 0.58614(12) 0.16812(6) 0.0412(3) Uani 1 1 d . . . . .
F5 F 0.7203(3) 0.38732(13) 0.20859(6) 0.0466(3) Uani 1 1 d . . . . .
O1 O 0.8409(2) 0.39452(11) 0.34633(6) 0.0208(3) Uani 1 1 d . . . . .
O2 O 0.4603(2) 0.54452(12) 0.31381(7) 0.0271(3) Uani 1 1 d . . . . .
O3 O 0.8649(2) 0.62508(12) 0.30734(7) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.7183(3) 0.34504(16) 0.41711(9) 0.0196(4) Uani 1 1 d . . . . .
H1 H 0.5358 0.3822 0.4211 0.024 Uiso 1 1 calc R U . . .
C2 C 0.8499(3) 0.38446(16) 0.47079(9) 0.0211(4) Uani 1 1 d . . . . .
H2 H 1.0360 0.3681 0.4581 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7873(3) 0.31480(17) 0.54385(9) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.8211 0.3484 0.5825 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6864(3) 0.20803(17) 0.55671(9) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.6513 0.1679 0.6042 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6256(3) 0.14810(17) 0.49955(9) 0.0218(4) Uani 1 1 d . . . . .
H5 H 0.6804 0.0534 0.5110 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7484(3) 0.19956(16) 0.42576(9) 0.0196(4) Uani 1 1 d . . . . .
H6 H 0.9325 0.1657 0.4241 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6423(3) 0.15118(16) 0.36975(9) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.7544(3) 0.03473(16) 0.35036(9) 0.0209(4) Uani 1 1 d . . . . .
H8 H 0.9025 -0.0102 0.3702 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6532(3) -0.01673(16) 0.30252(9) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.7335 -0.0960 0.2902 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4350(3) 0.04633(16) 0.27227(9) 0.0198(4) Uani 1 1 d . . . . .
C11 C 0.3245(3) 0.16309(17) 0.29195(9) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.1759 0.2080 0.2723 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4258(3) 0.21485(16) 0.33916(9) 0.0223(4) Uani 1 1 d . . . . .
H12 H 0.3470 0.2948 0.3509 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3176(3) -0.00191(16) 0.21861(9) 0.0208(4) Uani 1 1 d . . . . .
H13 H 0.1324 0.0283 0.2250 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4125(3) 0.05691(17) 0.14320(9) 0.0231(4) Uani 1 1 d . . . . .
H14A H 0.3793 0.1515 0.1373 0.028 Uiso 1 1 calc R U . . .
H14B H 0.5966 0.0304 0.1351 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2828(3) 0.01419(17) 0.08901(9) 0.0236(4) Uani 1 1 d . . . . .
H15A H 0.3503 0.0520 0.0411 0.028 Uiso 1 1 calc R U . . .
H15B H 0.1003 0.0466 0.0948 0.028 Uiso 1 1 calc R U . . .
C16 C 0.3219(3) -0.13229(17) 0.09652(9) 0.0217(4) Uani 1 1 d . . . . .
H16 H 0.5069 -0.1626 0.0892 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2274(3) -0.19087(17) 0.17186(9) 0.0236(4) Uani 1 1 d . . . . .
H17A H 0.0430 -0.1649 0.1796 0.028 Uiso 1 1 calc R U . . .
H17B H 0.2613 -0.2855 0.1777 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3538(3) -0.14855(17) 0.22692(9) 0.0236(4) Uani 1 1 d . . . . .
H18A H 0.5360 -0.1822 0.2223 0.028 Uiso 1 1 calc R U . . .
H18B H 0.2820 -0.1853 0.2745 0.028 Uiso 1 1 calc R U . . .
C19 C 0.1974(3) -0.17344(18) 0.04088(9) 0.0250(4) Uani 1 1 d . . . . .
H19A H 0.2286 -0.1153 -0.0046 0.030 Uiso 1 1 calc R U . . .
H19B H 0.0134 -0.1627 0.0541 0.030 Uiso 1 1 calc R U . . .
C20 C 0.2877(4) -0.31148(19) 0.03039(11) 0.0326(5) Uani 1 1 d . . . . .
H20A H 0.4729 -0.3241 0.0193 0.039 Uiso 1 1 calc R U . . .
H20B H 0.2477 -0.3704 0.0749 0.039 Uiso 1 1 calc R U . . .
C21 C 0.1683(4) -0.3456(2) -0.02824(11) 0.0399(5) Uani 1 1 d . . . . .
H21A H 0.2077 -0.2878 -0.0725 0.048 Uiso 1 1 calc R U . . .
H21B H -0.0146 -0.3368 -0.0166 0.048 Uiso 1 1 calc R U . . .
H21C H 0.2347 -0.4342 -0.0333 0.048 Uiso 1 1 calc R U . . .
C22 C 0.8252(4) 0.48475(19) 0.21588(10) 0.0304(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4177(14) . ?
S1 O2 1.4216(13) . ?
S1 O1 1.5675(12) . ?
S1 C22 1.842(2) . ?
F1 C2 1.4089(19) . ?
F2 C5 1.4265(18) . ?
F3 C22 1.322(2) . ?
F4 C22 1.326(2) . ?
F5 C22 1.319(2) . ?
O1 C1 1.4880(19) . ?
C1 C2 1.508(2) . ?
C1 C6 1.525(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.496(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.325(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.495(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.541(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.517(2) . ?
C6 H6 1.0000 . ?
C7 C12 1.396(2) . ?
C7 C8 1.397(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(2) . ?
C10 C13 1.512(2) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.537(2) . ?
C13 C14 1.538(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.528(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.536(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C19 1.526(2) . ?
C16 C17 1.536(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.529(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.529(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 121.58(8) . . ?
O3 S1 O1 111.56(7) . . ?
O2 S1 O1 110.67(7) . . ?
O3 S1 C22 105.81(9) . . ?
O2 S1 C22 107.83(9) . . ?
O1 S1 C22 96.07(8) . . ?
C1 O1 S1 119.99(10) . . ?
O1 C1 C2 107.41(13) . . ?
O1 C1 C6 107.68(13) . . ?
C2 C1 C6 111.28(13) . . ?
O1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
C6 C1 H1 110.1 . . ?
F1 C2 C3 108.97(14) . . ?
F1 C2 C1 107.27(13) . . ?
C3 C2 C1 112.49(14) . . ?
F1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C4 C3 C2 122.47(16) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 122.71(16) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
F2 C5 C4 107.51(13) . . ?
F2 C5 C6 108.40(13) . . ?
C4 C5 C6 114.25(14) . . ?
F2 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C7 C6 C1 114.89(14) . . ?
C7 C6 C5 110.66(14) . . ?
C1 C6 C5 107.70(14) . . ?
C7 C6 H6 107.8 . . ?
C1 C6 H6 107.8 . . ?
C5 C6 H6 107.8 . . ?
C12 C7 C8 117.79(16) . . ?
C12 C7 C6 122.54(15) . . ?
C8 C7 C6 119.56(15) . . ?
C9 C8 C7 121.25(15) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.06(16) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 117.23(16) . . ?
C9 C10 C13 124.09(15) . . ?
C11 C10 C13 118.66(15) . . ?
C12 C11 C10 121.80(16) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 120.87(16) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C10 C13 C18 114.44(14) . . ?
C10 C13 C14 111.12(14) . . ?
C18 C13 C14 109.76(14) . . ?
C10 C13 H13 107.0 . . ?
C18 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C15 C14 C13 111.14(14) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 112.03(14) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C19 C16 C17 112.73(15) . . ?
C19 C16 C15 111.47(14) . . ?
C17 C16 C15 109.00(14) . . ?
C19 C16 H16 107.8 . . ?
C17 C16 H16 107.8 . . ?
C15 C16 H16 107.8 . . ?
C18 C17 C16 112.03(14) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C13 111.76(14) . . ?
C17 C18 H18A 109.3 . . ?
C13 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C13 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C16 C19 C20 114.87(15) . . ?
C16 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C16 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 112.83(16) . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F5 C22 F3 108.93(16) . . ?
F5 C22 F4 109.42(16) . . ?
F3 C22 F4 109.21(15) . . ?
F5 C22 S1 110.74(13) . . ?
F3 C22 S1 110.52(14) . . ?
F4 C22 S1 108.00(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 O1 C1 101.75(12) . . . . ?
O2 S1 O1 C1 -36.91(14) . . . . ?
C22 S1 O1 C1 -148.57(12) . . . . ?
S1 O1 C1 C2 -94.66(14) . . . . ?
S1 O1 C1 C6 145.39(11) . . . . ?
O1 C1 C2 F1 73.95(15) . . . . ?
C6 C1 C2 F1 -168.41(13) . . . . ?
O1 C1 C2 C3 -166.23(13) . . . . ?
C6 C1 C2 C3 -48.60(18) . . . . ?
F1 C2 C3 C4 136.10(17) . . . . ?
C1 C2 C3 C4 17.3(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 F2 -105.71(18) . . . . ?
C3 C4 C5 C6 14.6(2) . . . . ?
O1 C1 C6 C7 -57.19(17) . . . . ?
C2 C1 C6 C7 -174.66(13) . . . . ?
O1 C1 C6 C5 179.01(12) . . . . ?
C2 C1 C6 C5 61.54(17) . . . . ?
F2 C5 C6 C7 -50.39(17) . . . . ?
C4 C5 C6 C7 -170.23(14) . . . . ?
F2 C5 C6 C1 75.94(16) . . . . ?
C4 C5 C6 C1 -43.90(18) . . . . ?
C1 C6 C7 C12 -34.8(2) . . . . ?
C5 C6 C7 C12 87.38(19) . . . . ?
C1 C6 C7 C8 149.06(15) . . . . ?
C5 C6 C7 C8 -88.73(18) . . . . ?
C12 C7 C8 C9 -0.4(2) . . . . ?
C6 C7 C8 C9 175.89(15) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C10 C13 178.42(15) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C13 C10 C11 C12 -178.09(15) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C8 C7 C12 C11 0.8(2) . . . . ?
C6 C7 C12 C11 -175.34(15) . . . . ?
C9 C10 C13 C18 31.5(2) . . . . ?
C11 C10 C13 C18 -150.37(16) . . . . ?
C9 C10 C13 C14 -93.48(19) . . . . ?
C11 C10 C13 C14 84.63(18) . . . . ?
C10 C13 C14 C15 -176.75(14) . . . . ?
C18 C13 C14 C15 55.65(18) . . . . ?
C13 C14 C15 C16 -57.70(19) . . . . ?
C14 C15 C16 C19 -178.47(14) . . . . ?
C14 C15 C16 C17 56.46(19) . . . . ?
C19 C16 C17 C18 -179.95(14) . . . . ?
C15 C16 C17 C18 -55.62(19) . . . . ?
C16 C17 C18 C13 56.4(2) . . . . ?
C10 C13 C18 C17 179.09(14) . . . . ?
C14 C13 C18 C17 -55.19(19) . . . . ?
C17 C16 C19 C20 -73.9(2) . . . . ?
C15 C16 C19 C20 163.15(15) . . . . ?
C16 C19 C20 C21 -176.98(16) . . . . ?
O3 S1 C22 F5 175.77(12) . . . . ?
O2 S1 C22 F5 -52.72(15) . . . . ?
O1 S1 C22 F5 61.30(14) . . . . ?
O3 S1 C22 F3 54.95(15) . . . . ?
O2 S1 C22 F3 -173.53(12) . . . . ?
O1 S1 C22 F3 -59.52(14) . . . . ?
O3 S1 C22 F4 -64.45(15) . . . . ?
O2 S1 C22 F4 67.07(15) . . . . ?
O1 S1 C22 F4 -178.92(13) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
