# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

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

data_8
_database_code_depnum_ccdc_archive 'CCDC 2174305'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_8                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: All crystals were low-quality with poor diffraction at high angles.
;
_vrf_PLAT020_8                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.392 Report
RESPONSE: All crystals were low-quality with poor diffraction at high angles.
;
_vrf_PLAT026_8                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 25% Check
RESPONSE: All crystals were low-quality with poor diffraction at high angles.
;
# end Validation Reply Form

_audit_creation_date             2022-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H23 F5'
_chemical_formula_sum            'C14 H23 F5'
_chemical_formula_weight         286.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.5262(16)
_cell_length_b                   70.03(3)
_cell_length_c                   11.417(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.86(3)
_cell_angle_gamma                90
_cell_volume                     4324(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.9860
_cell_measurement_theta_min      3.8170
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3923
_diffrn_reflns_av_unetI/netI     0.2023
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       83
_diffrn_reflns_limit_k_min       -84
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45738
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.198
_diffrn_reflns_theta_min         2.524
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 200.00   0.50   15.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50   15.00    --  -30.00 -72.00 -90.00  146
  3  ω   -113.00 -71.00   0.50   15.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50   15.00   0.00 -67.00   0.00    --   400
  5  ω    -85.00 -13.00   0.50   15.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50   15.00    --  -67.00 180.00   0.00   80
  7  ω    -85.00 -12.00   0.50   15.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50   15.00    --  -67.00 180.00-180.00   80
  9  φ      0.00 200.00   0.50   15.00 -25.00-110.00   0.00    --   400
 10  ω   -128.00 -20.00   0.50   15.00    -- -110.00  72.00-135.00  216
 11  ω   -128.00 -20.00   0.50   15.00    -- -110.00  72.00  45.00  216
 12  ω   -115.00 -20.00   0.50   15.00    -- -110.00  72.00 -45.00  190
 13  ω   -113.00 -23.00   0.50   15.00    -- -110.00  72.00 135.00  180
 14  ω   -141.00 -46.00   0.50   15.00    -- -110.00 180.00 -90.00  190
 15  ω   -141.00 -46.00   0.50   15.00    -- -110.00 180.00-180.00  190
 16  ω   -141.00 -59.00   0.50   15.00    -- -110.00 180.00  90.00  164
 17  ω   -141.00 -55.00   0.50   15.00    -- -110.00 180.00   0.00  172
 18  ω   -141.00 -59.00   0.50   15.00    -- -110.00 180.00  45.00  164
 19  ω   -141.00 -78.00   0.50   15.00    -- -110.00 180.00 -45.00  126
 20  ω   -140.00 -77.00   0.50   15.00    -- -110.00 180.00-135.00  126
 21  ω   -140.00 -56.00   0.50   15.00    -- -110.00 180.00 135.00  168
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1096811000
_diffrn_orient_matrix_UB_12      -0.0134887000
_diffrn_orient_matrix_UB_13      0.0822686000
_diffrn_orient_matrix_UB_21      -0.0206674000
_diffrn_orient_matrix_UB_22      -0.0159851000
_diffrn_orient_matrix_UB_23      -0.0946320000
_diffrn_orient_matrix_UB_31      0.2614275000
_diffrn_orient_matrix_UB_32      -0.0068903000
_diffrn_orient_matrix_UB_33      0.0575283000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2053
_reflns_number_total             8073
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.0057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         8073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3485
_refine_ls_R_factor_gt           0.1646
_refine_ls_restrained_S_all      1.438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3423
_refine_ls_wR_factor_ref         0.4235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
  C46(H46)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
  C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C47(H47A,
 H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B),
 C52(H52A,H52B), C53(H53A,H53B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F2 F 0.7159(12) 0.73145(11) 0.7911(6) 0.097(2) Uani 1 1 d . . . . .
F3 F 0.9260(12) 0.76508(11) 0.7447(6) 0.099(2) Uani 1 1 d . . . . .
F4 F 0.5143(12) 0.76629(11) 0.8398(6) 0.099(2) Uani 1 1 d . . . . .
F5 F 0.5603(13) 0.77172(12) 1.0812(6) 0.106(3) Uani 1 1 d . . . . .
F6 F 0.5001(12) 0.73563(10) 0.9896(6) 0.100(2) Uani 1 1 d . . . . .
F22 F 0.3501(12) 0.44609(10) 0.3495(6) 0.096(2) Uani 1 1 d . . . . .
F23 F 0.3282(12) 0.48224(10) 0.2641(6) 0.095(2) Uani 1 1 d . . . . .
F24 F 0.5071(12) 0.47672(10) 0.5027(5) 0.089(2) Uani 1 1 d . . . . .
F25 F 1.0044(12) 0.47668(11) 0.5826(6) 0.100(2) Uani 1 1 d . . . . .
F26 F 0.7618(12) 0.44269(11) 0.5453(6) 0.100(2) Uani 1 1 d . . . . .
F42 F 0.2517(11) 0.44984(10) 0.8229(5) 0.087(2) Uani 1 1 d . . . . .
F43 F 0.3109(12) 0.48805(11) 0.8005(6) 0.099(2) Uani 1 1 d . . . . .
F44 F 0.4690(11) 0.47255(10) 1.0193(5) 0.092(2) Uani 1 1 d . . . . .
F45 F 0.9472(12) 0.46332(12) 1.0966(6) 0.102(2) Uani 1 1 d . . . . .
F46 F 0.6366(12) 0.43482(11) 1.0035(5) 0.096(2) Uani 1 1 d . . . . .
C1 C 0.930(2) 0.7314(2) 0.9932(11) 0.082(4) Uani 1 1 d . . . . .
H1 H 1.094500 0.734917 1.043291 0.098 Uiso 1 1 calc R U . . .
C2 C 0.938(2) 0.7376(2) 0.8695(11) 0.084(4) Uani 1 1 d . . . . .
H2 H 1.085869 0.732030 0.843943 0.101 Uiso 1 1 calc R U . . .
C3 C 0.946(3) 0.7591(2) 0.8650(11) 0.094(4) Uani 1 1 d . . . . .
H3 H 1.113122 0.763102 0.910205 0.113 Uiso 1 1 calc R U . . .
C4 C 0.757(2) 0.7701(2) 0.9153(11) 0.092(4) Uani 1 1 d . . . . .
H4 H 0.794593 0.784071 0.917460 0.111 Uiso 1 1 calc R U . . .
C5 C 0.758(2) 0.7628(2) 1.0369(10) 0.085(4) Uani 1 1 d . . . . .
H5 H 0.916868 0.766966 1.089653 0.102 Uiso 1 1 calc R U . . .
C6 C 0.740(2) 0.7415(2) 1.0492(11) 0.085(4) Uani 1 1 d . . . . .
H6 H 0.766336 0.738018 1.135874 0.102 Uiso 1 1 calc R U . . .
C7 C 0.908(2) 0.7096(2) 1.0066(10) 0.084(4) Uani 1 1 d . . . . .
H7A H 0.894618 0.706781 1.089905 0.100 Uiso 1 1 calc R U . . .
H7B H 0.753830 0.705284 0.953256 0.100 Uiso 1 1 calc R U . . .
C8 C 1.124(2) 0.6981(2) 0.9777(11) 0.098(4) Uani 1 1 d . . . . .
H8A H 1.122224 0.699353 0.891122 0.118 Uiso 1 1 calc R U . . .
H8B H 1.281147 0.703798 1.021710 0.118 Uiso 1 1 calc R U . . .
C9 C 1.121(2) 0.6771(2) 1.0091(13) 0.102(4) Uani 1 1 d . . . . .
H9A H 1.139641 0.675703 1.096737 0.122 Uiso 1 1 calc R U . . .
H9B H 0.960050 0.671526 0.970386 0.122 Uiso 1 1 calc R U . . .
C10 C 1.325(2) 0.66626(19) 0.9694(11) 0.087(4) Uani 1 1 d . . . . .
H10A H 1.485246 0.671999 1.008010 0.105 Uiso 1 1 calc R U . . .
H10B H 1.306312 0.667878 0.881844 0.105 Uiso 1 1 calc R U . . .
C11 C 1.333(2) 0.6450(2) 0.9975(12) 0.097(4) Uani 1 1 d . . . . .
H11A H 1.169751 0.639455 0.962620 0.116 Uiso 1 1 calc R U . . .
H11B H 1.360595 0.643448 1.085405 0.116 Uiso 1 1 calc R U . . .
C12 C 1.530(2) 0.6337(2) 0.9523(11) 0.088(4) Uani 1 1 d . . . . .
H12A H 1.503197 0.635386 0.864476 0.105 Uiso 1 1 calc R U . . .
H12B H 1.693454 0.639277 0.987474 0.105 Uiso 1 1 calc R U . . .
C13 C 1.540(2) 0.61257(19) 0.9788(11) 0.084(4) Uani 1 1 d . . . . .
H13A H 1.570930 0.610762 1.066636 0.101 Uiso 1 1 calc R U . . .
H13B H 1.377144 0.606897 0.944414 0.101 Uiso 1 1 calc R U . . .
C14 C 1.733(2) 0.6021(2) 0.9314(12) 0.100(5) Uani 1 1 d . . . . .
H14A H 1.698533 0.603055 0.843959 0.150 Uiso 1 1 calc R U . . .
H14B H 1.732081 0.588615 0.954764 0.150 Uiso 1 1 calc R U . . .
H14C H 1.895492 0.607634 0.964323 0.150 Uiso 1 1 calc R U . . .
C21 C 0.770(2) 0.44201(19) 0.3385(9) 0.076(3) Uani 1 1 d . . . . .
H21 H 0.886358 0.444997 0.284488 0.091 Uiso 1 1 calc R U . . .
C22 C 0.533(2) 0.4523(2) 0.2853(12) 0.087(4) Uani 1 1 d . . . . .
H22 H 0.479517 0.448917 0.198749 0.104 Uiso 1 1 calc R U . . .
C23 C 0.562(2) 0.4729(2) 0.2985(11) 0.084(4) Uani 1 1 d . . . . .
H23 H 0.669620 0.477278 0.243528 0.100 Uiso 1 1 calc R U . . .
C24 C 0.664(2) 0.4809(2) 0.4208(10) 0.083(4) Uani 1 1 d . . . . .
H24 H 0.690835 0.495022 0.416384 0.099 Uiso 1 1 calc R U . . .
C25 C 0.909(3) 0.4706(2) 0.4645(10) 0.091(4) Uani 1 1 d . . . . .
H25 H 1.025950 0.474752 0.413458 0.110 Uiso 1 1 calc R U . . .
C26 C 0.897(2) 0.4491(2) 0.4610(9) 0.084(4) Uani 1 1 d . . . . .
H26 H 1.068647 0.443758 0.481589 0.101 Uiso 1 1 calc R U . . .
C27 C 0.740(2) 0.4203(2) 0.3340(11) 0.088(4) Uani 1 1 d . . . . .
H27A H 0.663282 0.416701 0.250823 0.106 Uiso 1 1 calc R U . . .
H27B H 0.622014 0.416789 0.385033 0.106 Uiso 1 1 calc R U . . .
C28 C 0.975(2) 0.40849(18) 0.3734(11) 0.080(4) Uani 1 1 d . . . . .
H28A H 1.102312 0.413276 0.331382 0.096 Uiso 1 1 calc R U . . .
H28B H 1.036894 0.410404 0.460232 0.096 Uiso 1 1 calc R U . . .
C29 C 0.940(2) 0.38741(18) 0.3493(11) 0.086(4) Uani 1 1 d . . . . .
H29A H 0.871412 0.385568 0.262840 0.103 Uiso 1 1 calc R U . . .
H29B H 0.815661 0.382580 0.393436 0.103 Uiso 1 1 calc R U . . .
C30 C 1.174(2) 0.37541(19) 0.3842(11) 0.085(4) Uani 1 1 d . . . . .
H30A H 1.306066 0.381115 0.348552 0.102 Uiso 1 1 calc R U . . .
H30B H 1.230240 0.375665 0.472333 0.102 Uiso 1 1 calc R U . . .
C31 C 1.134(2) 0.35503(19) 0.3433(11) 0.088(4) Uani 1 1 d . . . . .
H31A H 1.068032 0.354973 0.255828 0.106 Uiso 1 1 calc R U . . .
H31B H 1.006887 0.349302 0.382102 0.106 Uiso 1 1 calc R U . . .
C32 C 1.363(2) 0.3426(2) 0.3696(11) 0.087(4) Uani 1 1 d . . . . .
H32A H 1.420130 0.341692 0.457480 0.105 Uiso 1 1 calc R U . . .
H32B H 1.494882 0.348886 0.336963 0.105 Uiso 1 1 calc R U . . .
C33 C 1.326(2) 0.3223(2) 0.3184(14) 0.109(5) Uani 1 1 d . . . . .
H33A H 1.196253 0.315899 0.352034 0.131 Uiso 1 1 calc R U . . .
H33B H 1.266902 0.323167 0.230623 0.131 Uiso 1 1 calc R U . . .
C34 C 1.559(2) 0.3102(2) 0.3444(12) 0.106(5) Uani 1 1 d . . . . .
H34A H 1.525319 0.297832 0.304439 0.159 Uiso 1 1 calc R U . . .
H34B H 1.609918 0.308262 0.430963 0.159 Uiso 1 1 calc R U . . .
H34C H 1.690931 0.316742 0.314644 0.159 Uiso 1 1 calc R U . . .
C41 C 0.663(2) 0.4427(2) 0.8011(11) 0.086(4) Uani 1 1 d . . . . .
H41 H 0.787872 0.446964 0.754814 0.104 Uiso 1 1 calc R U . . .
C42 C 0.446(2) 0.4568(2) 0.7694(11) 0.088(4) Uani 1 1 d . . . . .
H42 H 0.388616 0.457539 0.680560 0.105 Uiso 1 1 calc R U . . .
C43 C 0.526(2) 0.4759(2) 0.8187(12) 0.090(4) Uani 1 1 d . . . . .
H43 H 0.643741 0.481231 0.771483 0.108 Uiso 1 1 calc R U . . .
C44 C 0.642(2) 0.4777(2) 0.9493(11) 0.088(4) Uani 1 1 d . . . . .
H44 H 0.705178 0.490938 0.968686 0.106 Uiso 1 1 calc R U . . .
C45 C 0.850(3) 0.4637(2) 0.9680(12) 0.095(4) Uani 1 1 d . . . . .
H45 H 0.981377 0.468483 0.927025 0.113 Uiso 1 1 calc R U . . .
C46 C 0.792(2) 0.4434(2) 0.9317(10) 0.084(4) Uani 1 1 d . . . . .
H46 H 0.950224 0.436000 0.942311 0.101 Uiso 1 1 calc R U . . .
C47 C 0.584(2) 0.42258(18) 0.7549(10) 0.079(4) Uani 1 1 d . . . . .
H47A H 0.493504 0.423503 0.670784 0.095 Uiso 1 1 calc R U . . .
H47B H 0.470180 0.417208 0.802693 0.095 Uiso 1 1 calc R U . . .
C48 C 0.808(2) 0.40869(19) 0.7613(11) 0.085(4) Uani 1 1 d . . . . .
H48A H 0.931285 0.414774 0.721343 0.102 Uiso 1 1 calc R U . . .
H48B H 0.887970 0.406705 0.846384 0.102 Uiso 1 1 calc R U . . .
C49 C 0.739(2) 0.3897(2) 0.7046(12) 0.094(4) Uani 1 1 d . . . . .
H49A H 0.671414 0.391458 0.618058 0.113 Uiso 1 1 calc R U . . .
H49B H 0.608020 0.383862 0.740548 0.113 Uiso 1 1 calc R U . . .
C50 C 0.958(2) 0.3762(2) 0.7207(11) 0.090(4) Uani 1 1 d . . . . .
H50A H 1.085059 0.382029 0.682228 0.108 Uiso 1 1 calc R U . . .
H50B H 1.029537 0.375176 0.807334 0.108 Uiso 1 1 calc R U . . .
C51 C 0.906(2) 0.35628(19) 0.6712(12) 0.089(4) Uani 1 1 d . . . . .
H51A H 0.843883 0.357111 0.583639 0.107 Uiso 1 1 calc R U . . .
H51B H 0.773723 0.350529 0.706553 0.107 Uiso 1 1 calc R U . . .
C52 C 1.133(2) 0.3431(2) 0.6961(12) 0.096(4) Uani 1 1 d . . . . .
H52A H 1.264157 0.348813 0.660039 0.115 Uiso 1 1 calc R U . . .
H52B H 1.196249 0.342464 0.783712 0.115 Uiso 1 1 calc R U . . .
C53 C 1.087(2) 0.32281(19) 0.6490(12) 0.097(4) Uani 1 1 d . . . . .
H53A H 0.957303 0.316957 0.685922 0.116 Uiso 1 1 calc R U . . .
H53B H 1.021686 0.323374 0.561536 0.116 Uiso 1 1 calc R U . . .
C54 C 1.313(2) 0.3101(2) 0.6730(13) 0.114(5) Uani 1 1 d . . . . .
H54A H 1.269462 0.297448 0.637722 0.170 Uiso 1 1 calc R U . . .
H54B H 1.373008 0.308749 0.759543 0.170 Uiso 1 1 calc R U . . .
H54C H 1.442777 0.315742 0.637192 0.170 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.430(12) . ?
F3 C3 1.419(12) . ?
F4 C4 1.462(12) . ?
F5 C5 1.437(12) . ?
F6 C6 1.422(12) . ?
F22 C22 1.431(12) . ?
F23 C23 1.428(12) . ?
F24 C24 1.429(11) . ?
F25 C25 1.410(12) . ?
F26 C26 1.407(11) . ?
F42 C42 1.425(12) . ?
F43 C43 1.442(13) . ?
F44 C44 1.414(11) . ?
F45 C45 1.457(13) . ?
F46 C46 1.435(11) . ?
C1 H1 1.0000 . ?
C1 C2 1.488(15) . ?
C1 C6 1.512(15) . ?
C1 C7 1.537(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.504(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.507(16) . ?
C4 H4 1.0000 . ?
C4 C5 1.478(15) . ?
C5 H5 1.0000 . ?
C5 C6 1.505(17) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.531(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.518(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.501(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.520(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.509(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.484(14) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 H21 1.0000 . ?
C21 C22 1.510(15) . ?
C21 C26 1.513(15) . ?
C21 C27 1.526(16) . ?
C22 H22 1.0000 . ?
C22 C23 1.455(16) . ?
C23 H23 1.0000 . ?
C23 C24 1.505(15) . ?
C24 H24 1.0000 . ?
C24 C25 1.527(16) . ?
C25 H25 1.0000 . ?
C25 C26 1.506(17) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.528(14) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.506(15) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.526(14) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.504(15) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.513(15) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.531(17) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.517(16) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C41 H41 1.0000 . ?
C41 C42 1.537(16) . ?
C41 C46 1.516(15) . ?
C41 C47 1.532(16) . ?
C42 H42 1.0000 . ?
C42 C43 1.484(17) . ?
C43 H43 1.0000 . ?
C43 C44 1.503(16) . ?
C44 H44 1.0000 . ?
C44 C45 1.491(17) . ?
C45 H45 1.0000 . ?
C45 C46 1.497(17) . ?
C46 H46 1.0000 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.563(15) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.497(16) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.513(15) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.511(16) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 C52 1.538(15) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 C53 1.519(17) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C53 C54 1.516(15) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 105.6 . . ?
C2 C1 C6 115.0(12) . . ?
C2 C1 C7 113.8(11) . . ?
C6 C1 H1 105.6 . . ?
C6 C1 C7 110.3(11) . . ?
C7 C1 H1 105.6 . . ?
F2 C2 C1 108.4(10) . . ?
F2 C2 H2 110.4 . . ?
F2 C2 C3 107.9(11) . . ?
C1 C2 H2 110.4 . . ?
C1 C2 C3 109.4(11) . . ?
C3 C2 H2 110.4 . . ?
F3 C3 C2 109.4(11) . . ?
F3 C3 H3 107.3 . . ?
F3 C3 C4 107.0(11) . . ?
C2 C3 H3 107.3 . . ?
C2 C3 C4 118.1(12) . . ?
C4 C3 H3 107.3 . . ?
F4 C4 C3 107.9(11) . . ?
F4 C4 H4 110.7 . . ?
F4 C4 C5 108.5(10) . . ?
C3 C4 H4 110.7 . . ?
C5 C4 C3 108.2(11) . . ?
C5 C4 H4 110.7 . . ?
F5 C5 C4 108.9(11) . . ?
F5 C5 H5 107.4 . . ?
F5 C5 C6 109.2(11) . . ?
C4 C5 H5 107.4 . . ?
C4 C5 C6 116.2(12) . . ?
C6 C5 H5 107.4 . . ?
F6 C6 C1 108.9(10) . . ?
F6 C6 C5 108.3(11) . . ?
F6 C6 H6 109.5 . . ?
C1 C6 H6 109.5 . . ?
C5 C6 C1 111.2(11) . . ?
C5 C6 H6 109.5 . . ?
C1 C7 H7A 108.6 . . ?
C1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C1 114.8(11) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.4(11) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.0(11) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C9 C10 C11 115.0(12) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.6(12) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
C13 C12 C11 116.4(11) . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.4(11) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C21 H21 105.5 . . ?
C22 C21 C26 114.6(11) . . ?
C22 C21 C27 112.3(11) . . ?
C26 C21 H21 105.5 . . ?
C26 C21 C27 112.5(10) . . ?
C27 C21 H21 105.5 . . ?
F22 C22 C21 107.2(10) . . ?
F22 C22 H22 109.9 . . ?
F22 C22 C23 108.8(11) . . ?
C21 C22 H22 109.9 . . ?
C23 C22 C21 111.3(11) . . ?
C23 C22 H22 109.9 . . ?
F23 C23 C22 110.7(11) . . ?
F23 C23 H23 107.9 . . ?
F23 C23 C24 103.2(10) . . ?
C22 C23 H23 107.9 . . ?
C22 C23 C24 118.7(12) . . ?
C24 C23 H23 107.9 . . ?
F24 C24 C23 111.5(10) . . ?
F24 C24 H24 110.8 . . ?
F24 C24 C25 107.7(10) . . ?
C23 C24 H24 110.8 . . ?
C23 C24 C25 105.2(10) . . ?
C25 C24 H24 110.8 . . ?
F25 C25 C24 107.5(10) . . ?
F25 C25 H25 107.9 . . ?
F25 C25 C26 109.5(10) . . ?
C24 C25 H25 107.9 . . ?
C26 C25 C24 115.9(12) . . ?
C26 C25 H25 107.9 . . ?
F26 C26 C21 108.5(10) . . ?
F26 C26 C25 109.0(11) . . ?
F26 C26 H26 109.4 . . ?
C21 C26 H26 109.4 . . ?
C25 C26 C21 111.1(10) . . ?
C25 C26 H26 109.4 . . ?
C21 C27 H27A 108.1 . . ?
C21 C27 H27B 108.1 . . ?
C21 C27 C28 116.7(10) . . ?
H27A C27 H27B 107.3 . . ?
C28 C27 H27A 108.1 . . ?
C28 C27 H27B 108.1 . . ?
C27 C28 H28A 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 C27 114.2(10) . . ?
C29 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C28 C29 H29A 108.5 . . ?
C28 C29 H29B 108.5 . . ?
C28 C29 C30 115.0(10) . . ?
H29A C29 H29B 107.5 . . ?
C30 C29 H29A 108.5 . . ?
C30 C29 H29B 108.5 . . ?
C29 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C31 C30 C29 112.3(11) . . ?
C31 C30 H30A 109.2 . . ?
C31 C30 H30B 109.2 . . ?
C30 C31 H31A 108.5 . . ?
C30 C31 H31B 108.5 . . ?
C30 C31 C32 115.0(11) . . ?
H31A C31 H31B 107.5 . . ?
C32 C31 H31A 108.5 . . ?
C32 C31 H31B 108.5 . . ?
C31 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C31 C32 C33 114.8(11) . . ?
H32A C32 H32B 107.5 . . ?
C33 C32 H32A 108.6 . . ?
C33 C32 H32B 108.6 . . ?
C32 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C34 C33 C32 113.8(12) . . ?
C34 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C42 C41 H41 105.8 . . ?
C46 C41 H41 105.8 . . ?
C46 C41 C42 113.5(12) . . ?
C46 C41 C47 114.3(11) . . ?
C47 C41 H41 105.8 . . ?
C47 C41 C42 111.0(11) . . ?
F42 C42 C41 107.4(10) . . ?
F42 C42 H42 110.1 . . ?
F42 C42 C43 109.6(10) . . ?
C41 C42 H42 110.1 . . ?
C43 C42 C41 109.5(12) . . ?
C43 C42 H42 110.1 . . ?
F43 C43 C42 107.9(11) . . ?
F43 C43 H43 108.0 . . ?
F43 C43 C44 105.4(11) . . ?
C42 C43 H43 108.0 . . ?
C42 C43 C44 119.0(13) . . ?
C44 C43 H43 108.0 . . ?
F44 C44 C43 109.7(10) . . ?
F44 C44 H44 110.9 . . ?
F44 C44 C45 110.0(12) . . ?
C43 C44 H44 110.9 . . ?
C45 C44 C43 104.3(11) . . ?
C45 C44 H44 110.9 . . ?
F45 C45 C44 105.6(11) . . ?
F45 C45 H45 108.9 . . ?
F45 C45 C46 106.0(11) . . ?
C44 C45 H45 108.9 . . ?
C44 C45 C46 118.1(12) . . ?
C46 C45 H45 108.9 . . ?
F46 C46 C41 109.3(10) . . ?
F46 C46 C45 110.9(10) . . ?
F46 C46 H46 109.0 . . ?
C41 C46 H46 109.0 . . ?
C45 C46 C41 109.5(11) . . ?
C45 C46 H46 109.0 . . ?
C41 C47 H47A 109.0 . . ?
C41 C47 H47B 109.0 . . ?
C41 C47 C48 113.0(10) . . ?
H47A C47 H47B 107.8 . . ?
C48 C47 H47A 109.0 . . ?
C48 C47 H47B 109.0 . . ?
C47 C48 H48A 108.8 . . ?
C47 C48 H48B 108.8 . . ?
H48A C48 H48B 107.7 . . ?
C49 C48 C47 113.9(10) . . ?
C49 C48 H48A 108.8 . . ?
C49 C48 H48B 108.8 . . ?
C48 C49 H49A 109.2 . . ?
C48 C49 H49B 109.2 . . ?
C48 C49 C50 112.0(11) . . ?
H49A C49 H49B 107.9 . . ?
C50 C49 H49A 109.2 . . ?
C50 C49 H49B 109.2 . . ?
C49 C50 H50A 108.2 . . ?
C49 C50 H50B 108.2 . . ?
H50A C50 H50B 107.3 . . ?
C51 C50 C49 116.4(11) . . ?
C51 C50 H50A 108.2 . . ?
C51 C50 H50B 108.2 . . ?
C50 C51 H51A 108.8 . . ?
C50 C51 H51B 108.8 . . ?
C50 C51 C52 113.7(11) . . ?
H51A C51 H51B 107.7 . . ?
C52 C51 H51A 108.8 . . ?
C52 C51 H51B 108.8 . . ?
C51 C52 H52A 108.5 . . ?
C51 C52 H52B 108.5 . . ?
H52A C52 H52B 107.5 . . ?
C53 C52 C51 115.1(11) . . ?
C53 C52 H52A 108.5 . . ?
C53 C52 H52B 108.5 . . ?
C52 C53 H53A 108.7 . . ?
C52 C53 H53B 108.7 . . ?
H53A C53 H53B 107.6 . . ?
C54 C53 C52 114.4(12) . . ?
C54 C53 H53A 108.7 . . ?
C54 C53 H53B 108.7 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 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
F2 C2 C3 F3 -55.7(13) . . . . ?
F2 C2 C3 C4 67.0(13) . . . . ?
F3 C3 C4 F4 57.6(15) . . . . ?
F3 C3 C4 C5 174.8(11) . . . . ?
F4 C4 C5 F5 -57.1(15) . . . . ?
F4 C4 C5 C6 66.8(14) . . . . ?
F5 C5 C6 F6 55.1(12) . . . . ?
F5 C5 C6 C1 174.7(9) . . . . ?
F22 C22 C23 F23 -53.6(13) . . . . ?
F22 C22 C23 C24 65.4(14) . . . . ?
F23 C23 C24 F24 60.7(13) . . . . ?
F23 C23 C24 C25 177.2(10) . . . . ?
F24 C24 C25 F25 -57.0(14) . . . . ?
F24 C24 C25 C26 65.8(13) . . . . ?
F25 C25 C26 F26 54.5(14) . . . . ?
F25 C25 C26 C21 173.9(10) . . . . ?
F42 C42 C43 F43 -55.2(13) . . . . ?
F42 C42 C43 C44 64.6(15) . . . . ?
F43 C43 C44 F44 57.2(15) . . . . ?
F43 C43 C44 C45 175.1(11) . . . . ?
F44 C44 C45 F45 -55.4(14) . . . . ?
F44 C44 C45 C46 62.9(15) . . . . ?
F45 C45 C46 F46 53.0(13) . . . . ?
F45 C45 C46 C41 173.7(10) . . . . ?
C1 C2 C3 F3 -173.5(9) . . . . ?
C1 C2 C3 C4 -50.7(15) . . . . ?
C1 C7 C8 C9 171.2(11) . . . . ?
C2 C1 C6 F6 69.6(15) . . . . ?
C2 C1 C6 C5 -49.6(15) . . . . ?
C2 C1 C7 C8 61.5(14) . . . . ?
C2 C3 C4 F4 -66.3(14) . . . . ?
C2 C3 C4 C5 50.9(16) . . . . ?
C3 C4 C5 F5 -173.8(11) . . . . ?
C3 C4 C5 C6 -50.0(15) . . . . ?
C4 C5 C6 F6 -68.5(13) . . . . ?
C4 C5 C6 C1 51.0(14) . . . . ?
C6 C1 C2 F2 -68.9(15) . . . . ?
C6 C1 C2 C3 48.6(15) . . . . ?
C6 C1 C7 C8 -167.5(10) . . . . ?
C7 C1 C2 F2 59.7(14) . . . . ?
C7 C1 C2 C3 177.1(11) . . . . ?
C7 C1 C6 F6 -60.7(14) . . . . ?
C7 C1 C6 C5 -179.9(10) . . . . ?
C7 C8 C9 C10 175.2(11) . . . . ?
C8 C9 C10 C11 -179.9(12) . . . . ?
C9 C10 C11 C12 177.0(11) . . . . ?
C10 C11 C12 C13 -179.7(11) . . . . ?
C11 C12 C13 C14 179.2(11) . . . . ?
C21 C22 C23 F23 -171.5(9) . . . . ?
C21 C22 C23 C24 -52.5(16) . . . . ?
C21 C27 C28 C29 -171.1(10) . . . . ?
C22 C21 C26 F26 73.5(14) . . . . ?
C22 C21 C26 C25 -46.3(15) . . . . ?
C22 C21 C27 C28 173.8(10) . . . . ?
C22 C23 C24 F24 -62.1(15) . . . . ?
C22 C23 C24 C25 54.3(15) . . . . ?
C23 C24 C25 F25 -176.0(11) . . . . ?
C23 C24 C25 C26 -53.2(14) . . . . ?
C24 C25 C26 F26 -67.3(12) . . . . ?
C24 C25 C26 C21 52.2(14) . . . . ?
C26 C21 C22 F22 -73.0(14) . . . . ?
C26 C21 C22 C23 45.8(15) . . . . ?
C26 C21 C27 C28 -55.2(14) . . . . ?
C27 C21 C22 F22 57.1(13) . . . . ?
C27 C21 C22 C23 175.9(11) . . . . ?
C27 C21 C26 F26 -56.4(14) . . . . ?
C27 C21 C26 C25 -176.2(11) . . . . ?
C27 C28 C29 C30 178.1(10) . . . . ?
C28 C29 C30 C31 -172.4(11) . . . . ?
C29 C30 C31 C32 177.1(10) . . . . ?
C30 C31 C32 C33 -175.0(12) . . . . ?
C31 C32 C33 C34 179.2(11) . . . . ?
C41 C42 C43 F43 -172.9(9) . . . . ?
C41 C42 C43 C44 -53.0(14) . . . . ?
C41 C47 C48 C49 -173.8(11) . . . . ?
C42 C41 C46 F46 72.7(14) . . . . ?
C42 C41 C46 C45 -49.0(15) . . . . ?
C42 C41 C47 C48 168.3(10) . . . . ?
C42 C43 C44 F44 -63.9(15) . . . . ?
C42 C43 C44 C45 53.9(15) . . . . ?
C43 C44 C45 F45 -173.0(10) . . . . ?
C43 C44 C45 C46 -54.7(15) . . . . ?
C44 C45 C46 F46 -65.2(14) . . . . ?
C44 C45 C46 C41 55.5(15) . . . . ?
C46 C41 C42 F42 -71.1(14) . . . . ?
C46 C41 C42 C43 47.9(14) . . . . ?
C46 C41 C47 C48 -61.8(14) . . . . ?
C47 C41 C42 F42 59.2(13) . . . . ?
C47 C41 C42 C43 178.3(10) . . . . ?
C47 C41 C46 F46 -56.0(14) . . . . ?
C47 C41 C46 C45 -177.6(11) . . . . ?
C47 C48 C49 C50 -175.9(10) . . . . ?
C48 C49 C50 C51 177.5(12) . . . . ?
C49 C50 C51 C52 -177.1(11) . . . . ?
C50 C51 C52 C53 179.2(12) . . . . ?
C51 C52 C53 C54 179.3(11) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_12c
_database_code_depnum_ccdc_archive 'CCDC 2174306'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-05-18
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C18 H32 F4'
_chemical_formula_moiety         'C18 H32 F4'
_chemical_formula_weight         324.44
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.7685(6)
_cell_length_b                   4.7401(2)
_cell_length_c                   17.0705(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.918(6)
_cell_angle_gamma                90.0000
_cell_volume                     924.30(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5235
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      74.41
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352.00
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.992

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            9955
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_theta_max         75.389
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3588
_reflns_number_gt                3013
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_max     0.897
_reflns_Friedel_fraction_full    0.935

#==============================================================================
# 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).

    Refined as a 2-component twin.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.1045
_refine_ls_wR_factor_ref         0.3408
_refine_ls_wR_factor_gt          0.3249
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3588
_refine_ls_number_parameters     204
_refine_ls_goodness_of_fit_ref   1.487
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)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         0.54
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.4(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables 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
F2 F 0.6807(3) 0.6977(9) 0.3015(2) 0.0427(9) Uani 1 1 d . . . . .
F4 F 0.5560(3) 0.6930(9) 0.4272(2) 0.0432(9) Uani 1 1 d . . . . .
F5 F 0.3531(3) 0.3929(10) 0.3790(2) 0.0480(10) Uani 1 1 d . . . . .
F6 F 0.4310(3) 0.6852(9) 0.2640(2) 0.0436(9) Uani 1 1 d . . . . .
C1 C 0.5595(5) 0.3105(15) 0.2452(4) 0.0386(13) Uani 1 1 d . . . . .
H1 H 0.561522 0.099675 0.243912 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6688(5) 0.4034(14) 0.3065(4) 0.0377(13) Uani 1 1 d . . . . .
H2 H 0.737564 0.314583 0.291285 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6732(5) 0.3206(15) 0.3931(4) 0.0385(13) Uani 1 1 d . . . . .
H3 H 0.678715 0.110151 0.395522 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5611(6) 0.3995(14) 0.4186(4) 0.0379(13) Uani 1 1 d . . . . .
H4 H 0.562349 0.308399 0.471615 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4540(6) 0.2984(16) 0.3563(4) 0.0417(13) Uani 1 1 d . . . . .
H5 H 0.453805 0.087483 0.357285 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4464(5) 0.3925(15) 0.2701(4) 0.0388(13) Uani 1 1 d . . . . .
H6 H 0.378166 0.297717 0.233177 0.047 Uiso 1 1 calc R U . . .
C7 C 0.5560(6) 0.4117(17) 0.1584(4) 0.0430(14) Uani 1 1 d . . . . .
H7A H 0.484848 0.335471 0.121107 0.052 Uiso 1 1 calc R U . . .
H7B H 0.550616 0.620092 0.156566 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6645(7) 0.3186(19) 0.1294(4) 0.0513(16) Uani 1 1 d . . . . .
H8A H 0.735538 0.398181 0.166015 0.062 Uiso 1 1 calc R U . . .
H8B H 0.670812 0.110379 0.132293 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6590(7) 0.414(2) 0.0430(4) 0.0521(17) Uani 1 1 d . . . . .
H9A H 0.656780 0.623025 0.040986 0.063 Uiso 1 1 calc R U . . .
H9B H 0.585589 0.343632 0.007101 0.063 Uiso 1 1 calc R U . . .
C10 C 0.7643(8) 0.310(2) 0.0106(5) 0.062(2) Uani 1 1 d . . . . .
H10 H 0.764545 0.098712 0.011841 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7444(10) 0.405(3) -0.0781(5) 0.077(3) Uani 1 1 d . . . . .
H11A H 0.810387 0.342878 -0.099595 0.093 Uiso 1 1 calc R U . . .
H11B H 0.738212 0.610638 -0.081100 0.093 Uiso 1 1 calc R U . . .
H11C H 0.671861 0.320384 -0.110034 0.093 Uiso 1 1 calc R U . . .
C12 C 0.8808(9) 0.411(3) 0.0599(6) 0.081(3) Uani 1 1 d . . . . .
H12A H 0.879856 0.617478 0.063729 0.097 Uiso 1 1 calc R U . . .
H12B H 0.942703 0.352948 0.033843 0.097 Uiso 1 1 calc R U . . .
H12C H 0.895706 0.329499 0.114126 0.097 Uiso 1 1 calc R U . . .
C13 C 0.7846(6) 0.4339(16) 0.4520(4) 0.0420(14) Uani 1 1 d . . . . .
H13A H 0.853422 0.379889 0.431522 0.050 Uiso 1 1 calc R U . . .
H13B H 0.780833 0.642556 0.452310 0.050 Uiso 1 1 calc R U . . .
C14 C 0.8030(6) 0.3285(18) 0.5383(4) 0.0464(15) Uani 1 1 d . . . . .
H14A H 0.804332 0.119693 0.538547 0.056 Uiso 1 1 calc R U . . .
H14B H 0.736682 0.390444 0.560454 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9176(6) 0.4392(17) 0.5923(4) 0.0459(15) Uani 1 1 d . . . . .
H15A H 0.982418 0.390578 0.567045 0.055 Uiso 1 1 calc R U . . .
H15B H 0.913143 0.647551 0.594427 0.055 Uiso 1 1 calc R U . . .
C16 C 0.9470(6) 0.3263(18) 0.6783(4) 0.0490(16) Uani 1 1 d . . . . .
H16 H 0.949775 0.115712 0.675951 0.059 Uiso 1 1 calc R U . . .
C17 C 1.0660(6) 0.432(2) 0.7244(5) 0.0586(19) Uani 1 1 d . . . . .
H17A H 1.067280 0.638452 0.722712 0.070 Uiso 1 1 calc R U . . .
H17B H 1.126641 0.356583 0.699617 0.070 Uiso 1 1 calc R U . . .
H17C H 1.080929 0.368662 0.780591 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8541(7) 0.411(3) 0.7234(5) 0.068(3) Uani 1 1 d . . . . .
H18A H 0.859642 0.614237 0.734653 0.082 Uiso 1 1 calc R U . . .
H18B H 0.867198 0.306847 0.774346 0.082 Uiso 1 1 calc R U . . .
H18C H 0.776015 0.367030 0.690041 0.082 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
F2 C2 1.406(8) . ?
F4 C4 1.402(8) . ?
F5 C5 1.407(8) . ?
F6 C6 1.400(8) . ?
C1 C2 1.515(9) . ?
C1 C6 1.541(8) . ?
C1 C7 1.547(9) . ?
C1 H1 1.0000 . ?
C2 C3 1.519(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.531(9) . ?
C3 C13 1.544(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.518(10) . ?
C4 H4 1.0000 . ?
C5 C6 1.521(9) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.541(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.531(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.554(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C12 1.505(15) . ?
C10 C11 1.543(12) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.522(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.531(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.521(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.516(10) . ?
C16 C18 1.536(11) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 112.5(5) . . ?
C2 C1 C7 113.2(5) . . ?
C6 C1 C7 111.1(5) . . ?
C2 C1 H1 106.5 . . ?
C6 C1 H1 106.5 . . ?
C7 C1 H1 106.5 . . ?
F2 C2 C1 109.1(5) . . ?
F2 C2 C3 109.5(5) . . ?
C1 C2 C3 115.0(5) . . ?
F2 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C2 C3 C4 112.5(5) . . ?
C2 C3 C13 111.6(5) . . ?
C4 C3 C13 112.6(5) . . ?
C2 C3 H3 106.5 . . ?
C4 C3 H3 106.5 . . ?
C13 C3 H3 106.5 . . ?
F4 C4 C5 109.7(5) . . ?
F4 C4 C3 109.5(5) . . ?
C5 C4 C3 110.6(5) . . ?
F4 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
F5 C5 C4 108.7(5) . . ?
F5 C5 C6 108.4(5) . . ?
C4 C5 C6 115.5(6) . . ?
F5 C5 H5 108.0 . . ?
C4 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
F6 C6 C5 109.8(5) . . ?
F6 C6 C1 109.5(5) . . ?
C5 C6 C1 109.9(5) . . ?
F6 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
C1 C6 H6 109.2 . . ?
C8 C7 C1 112.6(5) . . ?
C8 C7 H7A 109.1 . . ?
C1 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C1 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 112.3(6) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 113.3(7) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C12 C10 C11 111.0(8) . . ?
C12 C10 C9 113.3(7) . . ?
C11 C10 C9 108.1(8) . . ?
C12 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
C9 C10 H10 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 114.7(6) . . ?
C14 C13 H13A 108.6 . . ?
C3 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C3 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 111.7(6) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 115.0(6) . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C15 110.6(6) . . ?
C17 C16 C18 109.5(7) . . ?
C15 C16 C18 111.5(6) . . ?
C17 C16 H16 108.4 . . ?
C15 C16 H16 108.4 . . ?
C18 C16 H16 108.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 -73.1(6) . . . . ?
C7 C1 C2 F2 53.8(7) . . . . ?
C6 C1 C2 C3 50.3(8) . . . . ?
C7 C1 C2 C3 177.2(5) . . . . ?
F2 C2 C3 C4 73.4(7) . . . . ?
C1 C2 C3 C4 -49.8(9) . . . . ?
F2 C2 C3 C13 -54.4(7) . . . . ?
C1 C2 C3 C13 -177.6(6) . . . . ?
C2 C3 C4 F4 -71.6(7) . . . . ?
C13 C3 C4 F4 55.7(7) . . . . ?
C2 C3 C4 C5 49.4(8) . . . . ?
C13 C3 C4 C5 176.7(5) . . . . ?
F4 C4 C5 F5 -54.8(7) . . . . ?
C3 C4 C5 F5 -175.7(5) . . . . ?
F4 C4 C5 C6 67.2(7) . . . . ?
C3 C4 C5 C6 -53.7(8) . . . . ?
F5 C5 C6 F6 55.6(7) . . . . ?
C4 C5 C6 F6 -66.7(7) . . . . ?
F5 C5 C6 C1 176.1(5) . . . . ?
C4 C5 C6 C1 53.9(8) . . . . ?
C2 C1 C6 F6 70.5(7) . . . . ?
C7 C1 C6 F6 -57.6(7) . . . . ?
C2 C1 C6 C5 -50.2(8) . . . . ?
C7 C1 C6 C5 -178.3(6) . . . . ?
C2 C1 C7 C8 55.7(9) . . . . ?
C6 C1 C7 C8 -176.7(6) . . . . ?
C1 C7 C8 C9 178.8(6) . . . . ?
C7 C8 C9 C10 -176.9(7) . . . . ?
C8 C9 C10 C12 -60.0(12) . . . . ?
C8 C9 C10 C11 176.6(8) . . . . ?
C2 C3 C13 C14 -172.6(5) . . . . ?
C4 C3 C13 C14 59.7(8) . . . . ?
C3 C13 C14 C15 177.6(6) . . . . ?
C13 C14 C15 C16 -175.7(6) . . . . ?
C14 C15 C16 C17 175.8(6) . . . . ?
C14 C15 C16 C18 -62.1(9) . . . . ?


#==============================================================================
# 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_16e
_database_code_depnum_ccdc_archive 'CCDC 2174308'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-05-18
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C30 H51 F3'
_chemical_formula_moiety         'C30 H51 F3'
_chemical_formula_weight         468.73
_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                   22.2117(8)
_cell_length_b                   4.74450(15)
_cell_length_c                   26.2704(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.597(3)
_cell_angle_gamma                90.0000
_cell_volume                     2765.62(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7223
_cell_measurement_theta_min      1.94
_cell_measurement_theta_max      67.93
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032.00
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_T_max  0.994

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            28075
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_theta_max         67.112
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_full        67.112
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4931
_reflns_number_gt                3975
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2436
_refine_ls_wR_factor_gt          0.2372
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4931
_refine_ls_number_parameters     299
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0442P)²+4.5644P] 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         0.38
_refine_diff_density_min         -0.29
_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
F2 F 0.30368(9) 0.1769(4) 0.70430(7) 0.0386(5) Uani 1 1 d . . . . .
F4 F 0.26306(9) 0.1810(4) 0.80724(7) 0.0388(5) Uani 1 1 d . . . . .
F6 F 0.17638(9) 0.1758(4) 0.72015(7) 0.0387(5) Uani 1 1 d . . . . .
C1 C 0.23485(15) 0.5560(8) 0.68798(12) 0.0332(8) Uani 1 1 d . . . . .
H1 H 0.234372 0.766565 0.686406 0.040 Uiso 1 1 calc R U . . .
C2 C 0.29714(16) 0.4723(7) 0.70889(12) 0.0344(8) Uani 1 1 d . . . . .
H2 H 0.327619 0.564575 0.687508 0.041 Uiso 1 1 calc R U . . .
C3 C 0.31025(15) 0.5602(8) 0.76439(12) 0.0329(7) Uani 1 1 d . . . . .
H3 H 0.311745 0.770802 0.764727 0.040 Uiso 1 1 calc R U . . .
C4 C 0.26049(16) 0.4759(7) 0.79828(12) 0.0334(8) Uani 1 1 d . . . . .
H4 H 0.267784 0.572961 0.831786 0.040 Uiso 1 1 calc R U . . .
C5 C 0.19772(15) 0.5558(8) 0.77794(12) 0.0328(8) Uani 1 1 d . . . . .
H5 H 0.195726 0.766270 0.778885 0.039 Uiso 1 1 calc R U . . .
C6 C 0.18520(16) 0.4710(7) 0.72262(12) 0.0346(8) Uani 1 1 d . . . . .
H6 H 0.147046 0.564899 0.710080 0.042 Uiso 1 1 calc R U . . .
C7 C 0.22187(16) 0.4506(8) 0.63303(12) 0.0357(8) Uani 1 1 d . . . . .
H7A H 0.223737 0.242139 0.632887 0.043 Uiso 1 1 calc R U . . .
H7B H 0.180345 0.506042 0.621948 0.043 Uiso 1 1 calc R U . . .
C8 C 0.26529(17) 0.5636(8) 0.59465(12) 0.0393(8) Uani 1 1 d . . . . .
H8A H 0.306855 0.511698 0.606229 0.047 Uiso 1 1 calc R U . . .
H8B H 0.262798 0.771969 0.594415 0.047 Uiso 1 1 calc R U . . .
C9 C 0.25375(17) 0.4561(8) 0.53987(13) 0.0403(9) Uani 1 1 d . . . . .
H9 H 0.255080 0.245475 0.540765 0.048 Uiso 1 1 calc R U . . .
C10 C 0.19234(19) 0.5434(10) 0.51710(14) 0.0492(10) Uani 1 1 d . . . . .
H10A H 0.188911 0.751356 0.517917 0.059 Uiso 1 1 calc R U . . .
H10B H 0.160403 0.464184 0.537970 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1829(2) 0.4401(11) 0.46192(15) 0.0605(12) Uani 1 1 d . . . . .
H11A H 0.182636 0.231509 0.461374 0.073 Uiso 1 1 calc R U . . .
H11B H 0.143319 0.506773 0.447799 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2321(3) 0.5474(11) 0.42927(15) 0.0672(14) Uani 1 1 d . . . . .
H12A H 0.230148 0.755631 0.427478 0.081 Uiso 1 1 calc R U . . .
H12B H 0.225833 0.472530 0.394252 0.081 Uiso 1 1 calc R U . . .
C13 C 0.2937(2) 0.4578(11) 0.45092(15) 0.0632(13) Uani 1 1 d . . . . .
H13A H 0.325283 0.538872 0.429952 0.076 Uiso 1 1 calc R U . . .
H13B H 0.297009 0.249880 0.449490 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3037(2) 0.5569(10) 0.50642(14) 0.0524(11) Uani 1 1 d . . . . .
H14A H 0.342860 0.484337 0.520290 0.063 Uiso 1 1 calc R U . . .
H14B H 0.305369 0.765379 0.507227 0.063 Uiso 1 1 calc R U . . .
C15 C 0.37299(16) 0.4571(8) 0.78355(13) 0.0390(8) Uani 1 1 d . . . . .
H15A H 0.372887 0.248501 0.784440 0.047 Uiso 1 1 calc R U . . .
H15B H 0.402997 0.516763 0.758976 0.047 Uiso 1 1 calc R U . . .
C16 C 0.39243(17) 0.5669(9) 0.83609(14) 0.0438(9) Uani 1 1 d . . . . .
H16A H 0.362402 0.507045 0.860627 0.053 Uiso 1 1 calc R U . . .
H16B H 0.392390 0.775543 0.835175 0.053 Uiso 1 1 calc R U . . .
C17 C 0.45471(17) 0.4661(9) 0.85534(13) 0.0421(9) Uani 1 1 d . . . . .
H17 H 0.453664 0.255427 0.856414 0.051 Uiso 1 1 calc R U . . .
C18 C 0.50548(17) 0.5512(10) 0.82162(15) 0.0503(10) Uani 1 1 d . . . . .
H18A H 0.505516 0.758771 0.817839 0.060 Uiso 1 1 calc R U . . .
H18B H 0.498065 0.467977 0.787351 0.060 Uiso 1 1 calc R U . . .
C19 C 0.56705(18) 0.4561(11) 0.84299(17) 0.0588(12) Uani 1 1 d . . . . .
H19A H 0.598596 0.526056 0.820730 0.071 Uiso 1 1 calc R U . . .
H19B H 0.568769 0.247636 0.843115 0.071 Uiso 1 1 calc R U . . .
C20 C 0.5796(2) 0.5653(12) 0.89700(18) 0.0647(13) Uani 1 1 d . . . . .
H20A H 0.618870 0.491290 0.910487 0.078 Uiso 1 1 calc R U . . .
H20B H 0.582146 0.773631 0.896460 0.078 Uiso 1 1 calc R U . . .
C21 C 0.5307(2) 0.4757(13) 0.93121(17) 0.0676(14) Uani 1 1 d . . . . .
H21A H 0.538537 0.558057 0.965506 0.081 Uiso 1 1 calc R U . . .
H21B H 0.531251 0.267904 0.934673 0.081 Uiso 1 1 calc R U . . .
C22 C 0.46834(19) 0.5707(12) 0.91000(15) 0.0582(12) Uani 1 1 d . . . . .
H22A H 0.437107 0.498303 0.932328 0.070 Uiso 1 1 calc R U . . .
H22B H 0.466372 0.779163 0.910479 0.070 Uiso 1 1 calc R U . . .
C23 C 0.14973(16) 0.4492(8) 0.81343(13) 0.0380(8) Uani 1 1 d . . . . .
H23A H 0.148991 0.240739 0.811867 0.046 Uiso 1 1 calc R U . . .
H23B H 0.162083 0.502939 0.848792 0.046 Uiso 1 1 calc R U . . .
C24 C 0.08592(16) 0.5575(9) 0.80191(13) 0.0394(8) Uani 1 1 d . . . . .
H24A H 0.071688 0.488010 0.767928 0.047 Uiso 1 1 calc R U . . .
H24B H 0.086907 0.765986 0.800411 0.047 Uiso 1 1 calc R U . . .
C25 C 0.04098(16) 0.4675(8) 0.84106(13) 0.0390(8) Uani 1 1 d . . . . .
H25 H 0.042956 0.257566 0.843988 0.047 Uiso 1 1 calc R U . . .
C26 C 0.05671(17) 0.5899(10) 0.89359(13) 0.0489(10) Uani 1 1 d . . . . .
H26A H 0.097587 0.526207 0.904934 0.059 Uiso 1 1 calc R U . . .
H26B H 0.057491 0.798115 0.891157 0.059 Uiso 1 1 calc R U . . .
C27 C 0.01255(19) 0.5043(12) 0.93302(16) 0.0637(14) Uani 1 1 d . . . . .
H27A H 0.023043 0.602164 0.965503 0.076 Uiso 1 1 calc R U . . .
H27B H 0.015945 0.298907 0.939188 0.076 Uiso 1 1 calc R U . . .
C28 C -0.05217(19) 0.5752(11) 0.91617(16) 0.0587(12) Uani 1 1 d . . . . .
H28A H -0.079839 0.499831 0.941343 0.070 Uiso 1 1 calc R U . . .
H28B H -0.057160 0.782514 0.914907 0.070 Uiso 1 1 calc R U . . .
C29 C -0.06852(18) 0.4512(11) 0.86397(16) 0.0546(11) Uani 1 1 d . . . . .
H29A H -0.109568 0.512913 0.852696 0.066 Uiso 1 1 calc R U . . .
H29B H -0.068497 0.242915 0.866155 0.066 Uiso 1 1 calc R U . . .
C30 C -0.02355(17) 0.5461(10) 0.82516(14) 0.0472(10) Uani 1 1 d . . . . .
H30A H -0.034349 0.458418 0.791793 0.057 Uiso 1 1 calc R U . . .
H30B H -0.026350 0.753155 0.820945 0.057 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
F2 C2 1.415(4) . ?
F4 C4 1.419(4) . ?
F6 C6 1.415(4) . ?
C1 C6 1.516(5) . ?
C1 C2 1.518(5) . ?
C1 C7 1.542(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.532(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.505(5) . ?
C3 C15 1.540(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.518(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.521(4) . ?
C5 C23 1.533(5) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.524(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.537(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(5) . ?
C9 C14 1.523(5) . ?
C9 H9 1.0000 . ?
C10 C11 1.536(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.507(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.518(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.520(5) . ?
C17 C22 1.536(5) . ?
C17 H17 1.0000 . ?
C18 C19 1.523(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.525(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.502(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.538(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.525(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.526(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C30 1.521(5) . ?
C25 C26 1.523(5) . ?
C25 H25 1.0000 . ?
C26 C27 1.514(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.523(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.521(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.527(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?

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 C1 C2 112.9(3) . . ?
C6 C1 C7 111.4(3) . . ?
C2 C1 C7 112.5(3) . . ?
C6 C1 H1 106.5 . . ?
C2 C1 H1 106.5 . . ?
C7 C1 H1 106.5 . . ?
F2 C2 C1 108.9(3) . . ?
F2 C2 C3 109.6(3) . . ?
C1 C2 C3 113.8(3) . . ?
F2 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C4 C3 C2 112.2(3) . . ?
C4 C3 C15 113.6(3) . . ?
C2 C3 C15 110.8(3) . . ?
C4 C3 H3 106.6 . . ?
C2 C3 H3 106.6 . . ?
C15 C3 H3 106.6 . . ?
F4 C4 C3 109.6(3) . . ?
F4 C4 C5 109.5(3) . . ?
C3 C4 C5 114.4(3) . . ?
F4 C4 H4 107.7 . . ?
C3 C4 H4 107.7 . . ?
C5 C4 H4 107.7 . . ?
C4 C5 C6 113.3(3) . . ?
C4 C5 C23 110.9(3) . . ?
C6 C5 C23 113.1(3) . . ?
C4 C5 H5 106.3 . . ?
C6 C5 H5 106.3 . . ?
C23 C5 H5 106.3 . . ?
F6 C6 C1 109.8(3) . . ?
F6 C6 C5 108.9(3) . . ?
C1 C6 C5 113.4(3) . . ?
F6 C6 H6 108.2 . . ?
C1 C6 H6 108.2 . . ?
C5 C6 H6 108.2 . . ?
C8 C7 C1 114.1(3) . . ?
C8 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 114.8(3) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C14 110.5(3) . . ?
C10 C9 C8 112.7(3) . . ?
C14 C9 C8 109.9(3) . . ?
C10 C9 H9 107.8 . . ?
C14 C9 H9 107.8 . . ?
C8 C9 H9 107.8 . . ?
C9 C10 C11 111.5(3) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 111.0(4) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.9(4) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.0(4) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C9 C14 C13 111.9(4) . . ?
C9 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C9 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C3 113.8(3) . . ?
C16 C15 H15A 108.8 . . ?
C3 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C3 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 114.1(3) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 114.1(3) . . ?
C18 C17 C22 109.8(3) . . ?
C16 C17 C22 110.2(3) . . ?
C18 C17 H17 107.5 . . ?
C16 C17 H17 107.5 . . ?
C22 C17 H17 107.5 . . ?
C17 C18 C19 112.6(3) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 111.5(4) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C19 110.7(4) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 C22 111.4(4) . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C17 C22 C21 112.3(4) . . ?
C17 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C17 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C5 115.7(3) . . ?
C24 C23 H23A 108.4 . . ?
C5 C23 H23A 108.4 . . ?
C24 C23 H23B 108.4 . . ?
C5 C23 H23B 108.4 . . ?
H23A C23 H23B 107.4 . . ?
C23 C24 C25 113.7(3) . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C30 C25 C26 109.3(3) . . ?
C30 C25 C24 112.5(3) . . ?
C26 C25 C24 112.0(3) . . ?
C30 C25 H25 107.6 . . ?
C26 C25 H25 107.6 . . ?
C24 C25 H25 107.6 . . ?
C27 C26 C25 112.9(4) . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26B 109.0 . . ?
C25 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C26 C27 C28 112.0(3) . . ?
C26 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C28 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C29 C28 C27 111.1(4) . . ?
C29 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
C29 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C28 C29 C30 110.6(4) . . ?
C28 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C25 C30 C29 112.4(3) . . ?
C25 C30 H30A 109.1 . . ?
C29 C30 H30A 109.1 . . ?
C25 C30 H30B 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 72.8(3) . . . . ?
C7 C1 C2 F2 -54.4(4) . . . . ?
C6 C1 C2 C3 -49.8(4) . . . . ?
C7 C1 C2 C3 -176.9(3) . . . . ?
F2 C2 C3 C4 -72.8(4) . . . . ?
C1 C2 C3 C4 49.4(4) . . . . ?
F2 C2 C3 C15 55.4(4) . . . . ?
C1 C2 C3 C15 177.6(3) . . . . ?
C2 C3 C4 F4 74.5(3) . . . . ?
C15 C3 C4 F4 -52.1(4) . . . . ?
C2 C3 C4 C5 -48.8(4) . . . . ?
C15 C3 C4 C5 -175.5(3) . . . . ?
F4 C4 C5 C6 -74.6(3) . . . . ?
C3 C4 C5 C6 48.8(4) . . . . ?
F4 C4 C5 C23 53.8(4) . . . . ?
C3 C4 C5 C23 177.2(3) . . . . ?
C2 C1 C6 F6 -73.1(4) . . . . ?
C7 C1 C6 F6 54.6(4) . . . . ?
C2 C1 C6 C5 49.0(4) . . . . ?
C7 C1 C6 C5 176.7(3) . . . . ?
C4 C5 C6 F6 74.2(4) . . . . ?
C23 C5 C6 F6 -53.0(4) . . . . ?
C4 C5 C6 C1 -48.3(4) . . . . ?
C23 C5 C6 C1 -175.5(3) . . . . ?
C6 C1 C7 C8 171.8(3) . . . . ?
C2 C1 C7 C8 -60.3(4) . . . . ?
C1 C7 C8 C9 178.9(3) . . . . ?
C7 C8 C9 C10 62.3(4) . . . . ?
C7 C8 C9 C14 -173.8(3) . . . . ?
C14 C9 C10 C11 54.9(5) . . . . ?
C8 C9 C10 C11 178.4(4) . . . . ?
C9 C10 C11 C12 -56.8(5) . . . . ?
C10 C11 C12 C13 57.1(5) . . . . ?
C11 C12 C13 C14 -56.1(5) . . . . ?
C10 C9 C14 C13 -54.2(5) . . . . ?
C8 C9 C14 C13 -179.2(4) . . . . ?
C12 C13 C14 C9 55.0(5) . . . . ?
C4 C3 C15 C16 -59.8(4) . . . . ?
C2 C3 C15 C16 172.8(3) . . . . ?
C3 C15 C16 C17 -179.9(3) . . . . ?
C15 C16 C17 C18 59.9(5) . . . . ?
C15 C16 C17 C22 -176.0(4) . . . . ?
C16 C17 C18 C19 177.9(4) . . . . ?
C22 C17 C18 C19 53.7(5) . . . . ?
C17 C18 C19 C20 -55.8(5) . . . . ?
C18 C19 C20 C21 56.0(6) . . . . ?
C19 C20 C21 C22 -55.7(6) . . . . ?
C18 C17 C22 C21 -53.3(5) . . . . ?
C16 C17 C22 C21 -179.8(4) . . . . ?
C20 C21 C22 C17 55.4(6) . . . . ?
C4 C5 C23 C24 170.2(3) . . . . ?
C6 C5 C23 C24 -61.3(4) . . . . ?
C5 C23 C24 C25 -174.7(3) . . . . ?
C23 C24 C25 C30 -172.6(3) . . . . ?
C23 C24 C25 C26 63.8(4) . . . . ?
C30 C25 C26 C27 54.4(5) . . . . ?
C24 C25 C26 C27 179.8(4) . . . . ?
C25 C26 C27 C28 -54.3(6) . . . . ?
C26 C27 C28 C29 53.7(6) . . . . ?
C27 C28 C29 C30 -54.7(5) . . . . ?
C26 C25 C30 C29 -56.0(5) . . . . ?
C24 C25 C30 C29 179.0(3) . . . . ?
C28 C29 C30 C25 57.1(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/pentane'
####################################################################### 
# 
# 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_16f
_database_code_depnum_ccdc_archive 'CCDC 2174309'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H57 F3 O3'
_chemical_formula_sum            'C33 H57 F3 O3'
_chemical_formula_weight         558.78
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   19.1482(8)
_cell_length_b                   4.7110(2)
_cell_length_c                   19.5670(9)
_cell_angle_alpha                90
_cell_angle_beta                 117.937(6)
_cell_angle_gamma                90
_cell_volume                     1559.39(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12655
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.7910
_cell_measurement_theta_min      2.6660
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.706
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15777
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 200.00   0.50    5.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50    5.00    --  -30.00 -72.00 -90.00  146
  3  ω   -111.00 -69.00   0.50    5.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50    5.00   0.00 -67.00   0.00    --   400
  5  ω    -83.00 -11.00   0.50    5.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50    5.00    --  -67.00 180.00   0.00   80
  7  ω    -83.00 -10.00   0.50    5.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50    5.00    --  -67.00 180.00-180.00   80
  9  φ      0.00 200.00   0.50   10.00 -25.00-110.00   0.00    --   400
 10  ω   -126.00 -20.00   0.50   10.00    -- -110.00  72.00-135.00  212
 11  ω   -126.00 -20.00   0.50   10.00    -- -110.00  72.00  45.00  212
 12  ω   -115.00 -20.00   0.50   10.00    -- -110.00  72.00 -45.00  190
 13  ω   -113.00 -23.00   0.50   10.00    -- -110.00  72.00 135.00  180
 14  ω   -141.00 -46.00   0.50   10.00    -- -110.00 180.00 -90.00  190
 15  ω   -141.00 -46.00   0.50   10.00    -- -110.00 180.00-180.00  190
 16  ω   -141.00 -59.00   0.50   10.00    -- -110.00 180.00  90.00  164
 17  ω   -141.00 -55.00   0.50   10.00    -- -110.00 180.00   0.00  172
 18  ω   -141.00 -59.00   0.50   10.00    -- -110.00 180.00  45.00  164
 19  ω   -141.00 -78.00   0.50   10.00    -- -110.00 180.00 -45.00  126
 20  ω   -140.00 -77.00   0.50   10.00    -- -110.00 180.00-135.00  126
 21  ω   -140.00 -56.00   0.50   10.00    -- -110.00 180.00 135.00  168
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0408198000
_diffrn_orient_matrix_UB_12      0.2625624000
_diffrn_orient_matrix_UB_13      0.0496718000
_diffrn_orient_matrix_UB_21      -0.0630529000
_diffrn_orient_matrix_UB_22      0.1930027000
_diffrn_orient_matrix_UB_23      -0.0615958000
_diffrn_orient_matrix_UB_31      -0.0515182000
_diffrn_orient_matrix_UB_32      -0.0282157000
_diffrn_orient_matrix_UB_33      0.0409340000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                5037
_reflns_number_total             5314
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Flack x determined using 1904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1763P)²+0.0445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C21(H21), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F2 F 0.34092(11) 0.2835(4) 0.64784(10) 0.0274(4) Uani 1 1 d . . . . .
F4 F 0.51289(11) 0.2837(4) 0.71056(11) 0.0275(4) Uani 1 1 d . . . . .
F6 F 0.41255(10) 0.2799(4) 0.54560(10) 0.0263(4) Uani 1 1 d . . . . .
O10 O 0.05050(13) 0.7076(6) 0.43292(15) 0.0357(6) Uani 1 1 d . . . . .
O20 O 0.32945(15) 0.7051(6) 0.90201(14) 0.0348(6) Uani 1 1 d . . . . .
O30 O 0.77894(15) 0.7230(7) 0.68745(16) 0.0424(7) Uani 1 1 d . . . . .
C1 C 0.34212(17) 0.6589(7) 0.56615(17) 0.0215(6) Uani 1 1 d . . . . .
H1 H 0.339377 0.870858 0.563362 0.026 Uiso 1 1 calc R U . . .
C2 C 0.35107(17) 0.5848(7) 0.64552(17) 0.0200(6) Uani 1 1 d . . . . .
H2 H 0.308462 0.682964 0.652376 0.024 Uiso 1 1 calc R U . . .
C3 C 0.43047(18) 0.6629(7) 0.71258(17) 0.0211(6) Uani 1 1 d . . . . .
H3 H 0.430787 0.874926 0.714943 0.025 Uiso 1 1 calc R U . . .
C4 C 0.50129(17) 0.5842(7) 0.70141(17) 0.0202(6) Uani 1 1 d . . . . .
H4 H 0.549176 0.681060 0.742167 0.024 Uiso 1 1 calc R U . . .
C5 C 0.49278(17) 0.6625(7) 0.62234(17) 0.0214(6) Uani 1 1 d . . . . .
H5 H 0.494743 0.874534 0.621621 0.026 Uiso 1 1 calc R U . . .
C6 C 0.41302(17) 0.5809(7) 0.55561(17) 0.0201(6) Uani 1 1 d . . . . .
H6 H 0.407540 0.674544 0.507477 0.024 Uiso 1 1 calc R U . . .
C7 C 0.26435(18) 0.5568(8) 0.49956(17) 0.0266(7) Uani 1 1 d . . . . .
H7A H 0.263201 0.611559 0.450198 0.032 Uiso 1 1 calc R U . . .
H7B H 0.262995 0.346935 0.501116 0.032 Uiso 1 1 calc R U . . .
C8 C 0.19039(19) 0.6718(9) 0.49999(19) 0.0312(7) Uani 1 1 d . . . . .
H8A H 0.188339 0.601609 0.546709 0.037 Uiso 1 1 calc R U . . .
H8B H 0.193439 0.881513 0.502950 0.037 Uiso 1 1 calc R U . . .
C9 C 0.11611(19) 0.5864(9) 0.4298(2) 0.0341(8) Uani 1 1 d . . . . .
H9A H 0.118008 0.651928 0.382586 0.041 Uiso 1 1 calc R U . . .
H9B H 0.111207 0.377037 0.427491 0.041 Uiso 1 1 calc R U . . .
C11 C -0.02409(19) 0.6013(8) 0.3762(2) 0.0298(7) Uani 1 1 d . . . . .
H11 H -0.021463 0.389241 0.377104 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0448(2) 0.7006(10) 0.2950(2) 0.0369(8) Uani 1 1 d . . . . .
H12A H -0.042472 0.910444 0.294456 0.044 Uiso 1 1 calc R U . . .
H12B H -0.005242 0.625734 0.280587 0.044 Uiso 1 1 calc R U . . .
C13 C -0.1267(2) 0.6035(10) 0.2357(2) 0.0415(9) Uani 1 1 d . . . . .
H13A H -0.127056 0.394179 0.231138 0.050 Uiso 1 1 calc R U . . .
H13B H -0.139232 0.685251 0.184614 0.050 Uiso 1 1 calc R U . . .
C14 C -0.1896(2) 0.6937(11) 0.2580(3) 0.0468(10) Uani 1 1 d . . . . .
H14A H -0.194703 0.903047 0.255087 0.056 Uiso 1 1 calc R U . . .
H14B H -0.241118 0.611486 0.220949 0.056 Uiso 1 1 calc R U . . .
C15 C -0.1687(2) 0.5965(10) 0.3391(3) 0.0421(9) Uani 1 1 d . . . . .
H15A H -0.171839 0.386805 0.339747 0.050 Uiso 1 1 calc R U . . .
H15B H -0.207980 0.673972 0.353672 0.050 Uiso 1 1 calc R U . . .
C16 C -0.0859(2) 0.6905(10) 0.3991(2) 0.0402(9) Uani 1 1 d . . . . .
H16A H -0.084913 0.899646 0.404536 0.048 Uiso 1 1 calc R U . . .
H16B H -0.073305 0.606158 0.449930 0.048 Uiso 1 1 calc R U . . .
C17 C 0.44028(18) 0.5632(8) 0.79114(18) 0.0271(7) Uani 1 1 d . . . . .
H17A H 0.438005 0.353310 0.791181 0.033 Uiso 1 1 calc R U . . .
H17B H 0.493198 0.621167 0.831903 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3783(2) 0.6800(9) 0.81108(19) 0.0311(7) Uani 1 1 d . . . . .
H18A H 0.379783 0.889951 0.810154 0.037 Uiso 1 1 calc R U . . .
H18B H 0.325366 0.618675 0.771009 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3897(2) 0.5848(9) 0.88905(19) 0.0321(8) Uani 1 1 d . . . . .
H19A H 0.387214 0.375171 0.890571 0.038 Uiso 1 1 calc R U . . .
H19B H 0.442077 0.646895 0.929902 0.038 Uiso 1 1 calc R U . . .
C21 C 0.3196(2) 0.5822(8) 0.96309(19) 0.0290(7) Uani 1 1 d . . . . .
H21 H 0.316525 0.371439 0.956161 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2411(2) 0.6862(11) 0.9548(2) 0.0402(9) Uani 1 1 d . . . . .
H22A H 0.198101 0.618786 0.904822 0.048 Uiso 1 1 calc R U . . .
H22B H 0.240574 0.896300 0.953889 0.048 Uiso 1 1 calc R U . . .
C23 C 0.2255(2) 0.5840(11) 1.0199(3) 0.0456(10) Uani 1 1 d . . . . .
H23A H 0.176797 0.675142 1.014908 0.055 Uiso 1 1 calc R U . . .
H23B H 0.216648 0.376327 1.015109 0.055 Uiso 1 1 calc R U . . .
C24 C 0.2927(3) 0.6498(10) 1.0982(2) 0.0455(10) Uani 1 1 d . . . . .
H24A H 0.282179 0.561696 1.138437 0.055 Uiso 1 1 calc R U . . .
H24B H 0.296006 0.857804 1.106445 0.055 Uiso 1 1 calc R U . . .
C25 C 0.3707(3) 0.5421(10) 1.1068(2) 0.0416(9) Uani 1 1 d . . . . .
H25A H 0.370188 0.331980 1.106312 0.050 Uiso 1 1 calc R U . . .
H25B H 0.413829 0.604656 1.157325 0.050 Uiso 1 1 calc R U . . .
C26 C 0.3871(2) 0.6494(9) 1.04242(19) 0.0343(8) Uani 1 1 d . . . . .
H26A H 0.395382 0.857349 1.047572 0.041 Uiso 1 1 calc R U . . .
H26B H 0.436225 0.560745 1.047594 0.041 Uiso 1 1 calc R U . . .
C27 C 0.56157(18) 0.5611(8) 0.60967(18) 0.0258(7) Uani 1 1 d . . . . .
H27A H 0.564437 0.351531 0.613871 0.031 Uiso 1 1 calc R U . . .
H27B H 0.550223 0.611025 0.556312 0.031 Uiso 1 1 calc R U . . .
C28 C 0.6422(2) 0.6829(10) 0.6657(2) 0.0367(8) Uani 1 1 d . . . . .
H28A H 0.640019 0.892604 0.662217 0.044 Uiso 1 1 calc R U . . .
H28B H 0.654893 0.629684 0.719265 0.044 Uiso 1 1 calc R U . . .
C29 C 0.7064(2) 0.5766(9) 0.6487(2) 0.0340(8) Uani 1 1 d . . . . .
H29A H 0.715710 0.373357 0.663008 0.041 Uiso 1 1 calc R U . . .
H29B H 0.687588 0.590346 0.592299 0.041 Uiso 1 1 calc R U . . .
C31 C 0.8385(2) 0.5955(8) 0.7562(2) 0.0336(8) Uani 1 1 d . . . . .
H31 H 0.835406 0.384797 0.749117 0.040 Uiso 1 1 calc R U . . .
C32 C 0.8303(2) 0.6653(12) 0.8271(3) 0.0461(10) Uani 1 1 d . . . . .
H32A H 0.780814 0.579401 0.821919 0.055 Uiso 1 1 calc R U . . .
H32B H 0.825787 0.873693 0.830327 0.055 Uiso 1 1 calc R U . . .
C33 C 0.8990(3) 0.5604(13) 0.9013(2) 0.0499(11) Uani 1 1 d . . . . .
H33A H 0.892893 0.630363 0.945956 0.060 Uiso 1 1 calc R U . . .
H33B H 0.898075 0.350344 0.902226 0.060 Uiso 1 1 calc R U . . .
C34 C 0.9779(2) 0.6584(12) 0.9097(2) 0.0477(10) Uani 1 1 d . . . . .
H34A H 1.020921 0.564645 0.955210 0.057 Uiso 1 1 calc R U . . .
H34B H 0.982969 0.865760 0.918863 0.057 Uiso 1 1 calc R U . . .
C35 C 0.9871(2) 0.5917(12) 0.8386(2) 0.0474(11) Uani 1 1 d . . . . .
H35A H 0.992340 0.383789 0.835119 0.057 Uiso 1 1 calc R U . . .
H35B H 1.036301 0.680937 0.844052 0.057 Uiso 1 1 calc R U . . .
C36 C 0.9175(2) 0.6969(10) 0.7643(2) 0.0415(9) Uani 1 1 d . . . . .
H36A H 0.918025 0.907021 0.763690 0.050 Uiso 1 1 calc R U . . .
H36B H 0.923498 0.628943 0.719454 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.436(4) . ?
F4 C4 1.431(4) . ?
F6 C6 1.431(4) . ?
O10 C9 1.407(4) . ?
O10 C11 1.427(4) . ?
O20 C19 1.410(4) . ?
O20 C21 1.418(4) . ?
O30 C29 1.412(5) . ?
O30 C31 1.426(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.521(4) . ?
C1 C6 1.511(4) . ?
C1 C7 1.526(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.516(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.517(4) . ?
C3 C17 1.532(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.523(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(4) . ?
C5 C27 1.527(4) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.497(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11 1.0000 . ?
C11 C12 1.519(5) . ?
C11 C16 1.509(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.519(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.521(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.515(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.531(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.516(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.505(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 H21 1.0000 . ?
C21 C22 1.515(5) . ?
C21 C26 1.517(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.516(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.501(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.511(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.520(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.526(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.501(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C31 H31 1.0000 . ?
C31 C32 1.506(5) . ?
C31 C36 1.522(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.515(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.514(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.514(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.524(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C11 114.3(3) . . ?
C19 O20 C21 115.5(3) . . ?
C29 O30 C31 116.9(3) . . ?
C2 C1 H1 105.2 . . ?
C2 C1 C7 113.4(2) . . ?
C6 C1 H1 105.2 . . ?
C6 C1 C2 113.9(3) . . ?
C6 C1 C7 112.7(2) . . ?
C7 C1 H1 105.2 . . ?
F2 C2 C1 107.9(2) . . ?
F2 C2 H2 108.8 . . ?
F2 C2 C3 107.9(2) . . ?
C1 C2 H2 108.8 . . ?
C3 C2 C1 114.5(2) . . ?
C3 C2 H2 108.8 . . ?
C2 C3 H3 105.3 . . ?
C2 C3 C4 114.7(2) . . ?
C2 C3 C17 113.3(2) . . ?
C4 C3 H3 105.3 . . ?
C4 C3 C17 111.8(3) . . ?
C17 C3 H3 105.3 . . ?
F4 C4 C3 108.7(2) . . ?
F4 C4 H4 108.7 . . ?
F4 C4 C5 107.6(2) . . ?
C3 C4 H4 108.7 . . ?
C3 C4 C5 114.2(3) . . ?
C5 C4 H4 108.7 . . ?
C4 C5 H5 105.6 . . ?
C4 C5 C27 113.5(3) . . ?
C6 C5 C4 113.4(2) . . ?
C6 C5 H5 105.6 . . ?
C6 C5 C27 112.2(2) . . ?
C27 C5 H5 105.6 . . ?
F6 C6 C1 108.1(2) . . ?
F6 C6 C5 107.9(2) . . ?
F6 C6 H6 108.5 . . ?
C1 C6 C5 115.2(2) . . ?
C1 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C1 C7 H7A 108.5 . . ?
C1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C1 115.0(3) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.7(3) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O10 C9 C8 109.6(3) . . ?
O10 C9 H9A 109.8 . . ?
O10 C9 H9B 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O10 C11 H11 108.2 . . ?
O10 C11 C12 112.4(3) . . ?
O10 C11 C16 108.0(3) . . ?
C12 C11 H11 108.2 . . ?
C16 C11 H11 108.2 . . ?
C16 C11 C12 111.6(3) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C11 112.2(3) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.6(3) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.1(3) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C14 C15 C16 112.7(3) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C11 C16 C15 111.5(3) . . ?
C11 C16 H16A 109.3 . . ?
C11 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C3 C17 H17A 108.8 . . ?
C3 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C3 113.9(3) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 C17 113.2(3) . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
O20 C19 C18 108.7(3) . . ?
O20 C19 H19A 110.0 . . ?
O20 C19 H19B 110.0 . . ?
C18 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
H19A C19 H19B 108.3 . . ?
O20 C21 H21 108.3 . . ?
O20 C21 C22 107.1(3) . . ?
O20 C21 C26 113.0(3) . . ?
C22 C21 H21 108.3 . . ?
C22 C21 C26 111.7(3) . . ?
C26 C21 H21 108.3 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C21 C22 C23 112.5(3) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C22 112.4(3) . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C23 C24 C25 111.9(3) . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C24 C25 C26 111.9(3) . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
C21 C26 C25 111.8(3) . . ?
C21 C26 H26A 109.3 . . ?
C21 C26 H26B 109.3 . . ?
C25 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?
C5 C27 H27A 108.5 . . ?
C5 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 C5 115.1(3) . . ?
C28 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C27 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 C27 111.9(3) . . ?
C29 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
O30 C29 C28 114.8(3) . . ?
O30 C29 H29A 108.6 . . ?
O30 C29 H29B 108.6 . . ?
C28 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.5 . . ?
O30 C31 H31 108.6 . . ?
O30 C31 C32 113.2(3) . . ?
O30 C31 C36 106.5(3) . . ?
C32 C31 H31 108.6 . . ?
C32 C31 C36 111.3(3) . . ?
C36 C31 H31 108.6 . . ?
C31 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C31 C32 C33 113.2(3) . . ?
H32A C32 H32B 107.8 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C32 C33 H33A 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C34 C33 C32 112.3(4) . . ?
C34 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C33 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
C33 C34 C35 112.2(4) . . ?
H34A C34 H34B 107.9 . . ?
C35 C34 H34A 109.2 . . ?
C35 C34 H34B 109.2 . . ?
C34 C35 H35A 109.1 . . ?
C34 C35 H35B 109.1 . . ?
C34 C35 C36 112.5(3) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C31 C36 C35 112.4(3) . . ?
C31 C36 H36A 109.1 . . ?
C31 C36 H36B 109.1 . . ?
C35 C36 H36A 109.1 . . ?
C35 C36 H36B 109.1 . . ?
H36A C36 H36B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C2 C3 C4 75.1(3) . . . . ?
F2 C2 C3 C17 -55.0(3) . . . . ?
F4 C4 C5 C6 74.9(3) . . . . ?
F4 C4 C5 C27 -54.7(3) . . . . ?
O10 C11 C12 C13 -176.1(3) . . . . ?
O10 C11 C16 C15 177.4(3) . . . . ?
O20 C21 C22 C23 -176.5(3) . . . . ?
O20 C21 C26 C25 173.8(3) . . . . ?
O30 C31 C32 C33 -172.9(4) . . . . ?
O30 C31 C36 C35 176.3(4) . . . . ?
C1 C2 C3 C4 -45.1(4) . . . . ?
C1 C2 C3 C17 -175.1(3) . . . . ?
C1 C7 C8 C9 174.8(3) . . . . ?
C2 C1 C6 F6 75.1(3) . . . . ?
C2 C1 C6 C5 -45.6(4) . . . . ?
C2 C1 C7 C8 58.7(4) . . . . ?
C2 C3 C4 F4 -74.4(3) . . . . ?
C2 C3 C4 C5 45.8(4) . . . . ?
C2 C3 C17 C18 -58.6(4) . . . . ?
C3 C4 C5 C6 -45.9(4) . . . . ?
C3 C4 C5 C27 -175.4(3) . . . . ?
C3 C17 C18 C19 -178.9(3) . . . . ?
C4 C3 C17 C18 169.9(3) . . . . ?
C4 C5 C6 F6 -74.6(3) . . . . ?
C4 C5 C6 C1 46.3(4) . . . . ?
C4 C5 C27 C28 -61.2(4) . . . . ?
C5 C27 C28 C29 -179.1(3) . . . . ?
C6 C1 C2 F2 -75.6(3) . . . . ?
C6 C1 C2 C3 44.6(4) . . . . ?
C6 C1 C7 C8 -170.0(3) . . . . ?
C6 C5 C27 C28 168.6(3) . . . . ?
C7 C1 C2 F2 55.2(3) . . . . ?
C7 C1 C2 C3 175.4(3) . . . . ?
C7 C1 C6 F6 -56.0(3) . . . . ?
C7 C1 C6 C5 -176.7(3) . . . . ?
C7 C8 C9 O10 -178.1(3) . . . . ?
C9 O10 C11 C12 -70.8(4) . . . . ?
C9 O10 C11 C16 165.6(3) . . . . ?
C11 O10 C9 C8 -169.5(3) . . . . ?
C11 C12 C13 C14 54.6(5) . . . . ?
C12 C11 C16 C15 53.3(5) . . . . ?
C12 C13 C14 C15 -53.7(5) . . . . ?
C13 C14 C15 C16 53.4(5) . . . . ?
C14 C15 C16 C11 -53.5(5) . . . . ?
C16 C11 C12 C13 -54.6(5) . . . . ?
C17 C3 C4 F4 56.4(3) . . . . ?
C17 C3 C4 C5 176.6(3) . . . . ?
C17 C18 C19 O20 179.8(3) . . . . ?
C19 O20 C21 C22 -166.1(3) . . . . ?
C19 O20 C21 C26 70.5(4) . . . . ?
C21 O20 C19 C18 164.8(3) . . . . ?
C21 C22 C23 C24 52.5(5) . . . . ?
C22 C21 C26 C25 53.0(5) . . . . ?
C22 C23 C24 C25 -53.0(5) . . . . ?
C23 C24 C25 C26 53.9(5) . . . . ?
C24 C25 C26 C21 -54.0(5) . . . . ?
C26 C21 C22 C23 -52.2(5) . . . . ?
C27 C5 C6 F6 55.6(3) . . . . ?
C27 C5 C6 C1 176.5(3) . . . . ?
C27 C28 C29 O30 167.6(3) . . . . ?
C29 O30 C31 C32 -84.5(4) . . . . ?
C29 O30 C31 C36 152.9(3) . . . . ?
C31 O30 C29 C28 98.4(4) . . . . ?
C31 C32 C33 C34 52.8(6) . . . . ?
C32 C31 C36 C35 52.5(5) . . . . ?
C32 C33 C34 C35 -51.5(6) . . . . ?
C33 C34 C35 C36 51.6(6) . . . . ?
C34 C35 C36 C31 -52.4(6) . . . . ?
C36 C31 C32 C33 -53.0(6) . . . . ?


#==END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/pentane'
####################################################################### 
# 
# 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_16d
_database_code_depnum_ccdc_archive 'CCDC 2174307'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2021-05-20
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C24 H45 F3'
_chemical_formula_moiety         'C24 H45 F3'
_chemical_formula_weight         390.61
_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                   19.3963(11)
_cell_length_b                   4.7331(3)
_cell_length_c                   26.5239(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.933(5)
_cell_angle_gamma                90.0000
_cell_volume                     2422.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10465
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      75.16
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864.00
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.376
_exptl_absorpt_correction_T_max  0.994

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            25361
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_theta_max         75.719
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4901
_reflns_number_gt                3943
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2604
_refine_ls_wR_factor_gt          0.2468
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4901
_refine_ls_number_parameters     250
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1817P)²+0.5317P] 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         1.07
_refine_diff_density_min         -0.34
_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
F2 F 0.71528(6) 0.1950(3) 0.32858(4) 0.0434(3) Uani 1 1 d . . . . .
F4 F 0.86106(5) 0.1986(3) 0.32116(4) 0.0415(3) Uani 1 1 d . . . . .
F6 F 0.76558(5) 0.1992(3) 0.22758(4) 0.0431(3) Uani 1 1 d . . . . .
C1 C 0.70846(9) 0.5725(5) 0.26833(7) 0.0395(5) Uani 1 1 d . . . . .
H1 H 0.705645 0.783449 0.267536 0.047 Uiso 1 1 calc R U . . .
C2 C 0.72202(10) 0.4928(4) 0.32385(8) 0.0380(5) Uani 1 1 d . . . . .
H2 H 0.685890 0.584996 0.342559 0.046 Uiso 1 1 calc R U . . .
C3 C 0.79283(9) 0.5782(5) 0.34909(7) 0.0384(4) Uani 1 1 d . . . . .
H3 H 0.792826 0.789375 0.350315 0.046 Uiso 1 1 calc R U . . .
C4 C 0.85107(10) 0.4956(4) 0.31777(7) 0.0370(4) Uani 1 1 d . . . . .
H4 H 0.894580 0.589816 0.332758 0.044 Uiso 1 1 calc R U . . .
C5 C 0.83885(10) 0.5777(5) 0.26217(7) 0.0383(4) Uani 1 1 d . . . . .
H5 H 0.840362 0.788850 0.261349 0.046 Uiso 1 1 calc R U . . .
C6 C 0.76724(10) 0.4948(4) 0.23718(8) 0.0371(4) Uani 1 1 d . . . . .
H6 H 0.759365 0.595044 0.203898 0.045 Uiso 1 1 calc R U . . .
C7 C 0.63667(10) 0.4667(5) 0.24656(8) 0.0449(5) Uani 1 1 d . . . . .
H7A H 0.637598 0.257558 0.246391 0.054 Uiso 1 1 calc R U . . .
H7B H 0.602590 0.525589 0.269827 0.054 Uiso 1 1 calc R U . . .
C8 C 0.61089(10) 0.5664(5) 0.19366(8) 0.0466(5) Uani 1 1 d . . . . .
H8A H 0.640200 0.484073 0.168995 0.056 Uiso 1 1 calc R U . . .
H8B H 0.614871 0.774654 0.191976 0.056 Uiso 1 1 calc R U . . .
C9 C 0.53533(10) 0.4799(5) 0.17943(9) 0.0488(5) Uani 1 1 d . . . . .
H9A H 0.532712 0.271091 0.180227 0.059 Uiso 1 1 calc R U . . .
H9B H 0.507456 0.552386 0.205870 0.059 Uiso 1 1 calc R U . . .
C10 C 0.50192(12) 0.5797(6) 0.12825(9) 0.0541(6) Uani 1 1 d . . . . .
H10 H 0.504746 0.790601 0.127369 0.065 Uiso 1 1 calc R U . . .
C11 C 0.53752(14) 0.4643(7) 0.08452(10) 0.0678(8) Uani 1 1 d . . . . .
H11A H 0.535876 0.257346 0.084990 0.081 Uiso 1 1 calc R U . . .
H11B H 0.585939 0.526878 0.087742 0.081 Uiso 1 1 calc R U . . .
H11C H 0.513832 0.533735 0.052490 0.081 Uiso 1 1 calc R U . . .
C12 C 0.42528(12) 0.4954(7) 0.12152(11) 0.0687(8) Uani 1 1 d . . . . .
H12A H 0.401782 0.575168 0.149250 0.082 Uiso 1 1 calc R U . . .
H12B H 0.421396 0.289006 0.121936 0.082 Uiso 1 1 calc R U . . .
H12C H 0.403641 0.568116 0.089083 0.082 Uiso 1 1 calc R U . . .
C13 C 0.80523(10) 0.4784(5) 0.40430(7) 0.0417(5) Uani 1 1 d . . . . .
H13A H 0.807355 0.269410 0.404682 0.050 Uiso 1 1 calc R U . . .
H13B H 0.850859 0.549749 0.419129 0.050 Uiso 1 1 calc R U . . .
C14 C 0.75039(12) 0.5730(5) 0.43758(8) 0.0491(5) Uani 1 1 d . . . . .
H14A H 0.748189 0.781975 0.437279 0.059 Uiso 1 1 calc R U . . .
H14B H 0.704728 0.501231 0.422901 0.059 Uiso 1 1 calc R U . . .
C15 C 0.76346(13) 0.4730(5) 0.49204(8) 0.0516(6) Uani 1 1 d . . . . .
H15A H 0.809947 0.538895 0.506117 0.062 Uiso 1 1 calc R U . . .
H15B H 0.764202 0.263898 0.492204 0.062 Uiso 1 1 calc R U . . .
C16 C 0.71053(15) 0.5729(6) 0.52693(9) 0.0613(7) Uani 1 1 d . . . . .
H16 H 0.712126 0.784047 0.527389 0.074 Uiso 1 1 calc R U . . .
C17 C 0.63685(16) 0.4880(7) 0.50775(12) 0.0716(8) Uani 1 1 d . . . . .
H17A H 0.633341 0.281485 0.506683 0.086 Uiso 1 1 calc R U . . .
H17B H 0.625029 0.564591 0.473626 0.086 Uiso 1 1 calc R U . . .
H17C H 0.604706 0.563194 0.530586 0.086 Uiso 1 1 calc R U . . .
C18 C 0.72886(19) 0.4731(7) 0.58113(10) 0.0741(9) Uani 1 1 d . . . . .
H18A H 0.776179 0.532569 0.592952 0.089 Uiso 1 1 calc R U . . .
H18B H 0.725797 0.266635 0.582401 0.089 Uiso 1 1 calc R U . . .
H18C H 0.696421 0.555900 0.602969 0.089 Uiso 1 1 calc R U . . .
C19 C 0.89837(10) 0.4770(5) 0.23304(7) 0.0416(5) Uani 1 1 d . . . . .
H19A H 0.942598 0.543433 0.251143 0.050 Uiso 1 1 calc R U . . .
H19B H 0.899143 0.267880 0.233445 0.050 Uiso 1 1 calc R U . . .
C20 C 0.89479(11) 0.5759(5) 0.17828(8) 0.0462(5) Uani 1 1 d . . . . .
H20A H 0.891314 0.784558 0.177391 0.055 Uiso 1 1 calc R U . . .
H20B H 0.852352 0.498543 0.159271 0.055 Uiso 1 1 calc R U . . .
C21 C 0.95762(10) 0.4851(5) 0.15220(8) 0.0456(5) Uani 1 1 d . . . . .
H21A H 0.999967 0.550722 0.172924 0.055 Uiso 1 1 calc R U . . .
H21B H 0.959079 0.276046 0.151519 0.055 Uiso 1 1 calc R U . . .
C22 C 0.95959(14) 0.5933(6) 0.09836(9) 0.0564(6) Uani 1 1 d . . . . .
H22 H 0.957889 0.804377 0.099065 0.068 Uiso 1 1 calc R U . . .
C23 C 1.02634(13) 0.5039(7) 0.07683(9) 0.0670(8) Uani 1 1 d . . . . .
H23A H 1.026963 0.297950 0.073062 0.080 Uiso 1 1 calc R U . . .
H23B H 1.066366 0.563575 0.099962 0.080 Uiso 1 1 calc R U . . .
H23C H 1.028520 0.592780 0.043665 0.080 Uiso 1 1 calc R U . . .
C24 C 0.89775(14) 0.4872(8) 0.06310(10) 0.0764(10) Uani 1 1 d . . . . .
H24A H 0.854615 0.544465 0.076465 0.092 Uiso 1 1 calc R U . . .
H24B H 0.899523 0.280685 0.060945 0.092 Uiso 1 1 calc R U . . .
H24C H 0.899431 0.568453 0.029262 0.092 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
F2 C2 1.422(2) . ?
F4 C4 1.420(2) . ?
F6 C6 1.422(2) . ?
C1 C2 1.517(3) . ?
C1 C6 1.521(3) . ?
C1 C7 1.535(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.519(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.521(3) . ?
C3 C13 1.534(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.520(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.527(3) . ?
C5 C19 1.530(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.531(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.512(4) . ?
C10 C12 1.532(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.521(4) . ?
C16 C18 1.520(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.521(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.524(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.521(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C24 1.528(4) . ?
C22 C23 1.528(4) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 113.75(16) . . ?
C2 C1 C7 110.10(16) . . ?
C6 C1 C7 114.74(17) . . ?
C2 C1 H1 105.8 . . ?
C6 C1 H1 105.8 . . ?
C7 C1 H1 105.8 . . ?
F2 C2 C1 108.91(16) . . ?
F2 C2 C3 108.18(15) . . ?
C1 C2 C3 114.83(16) . . ?
F2 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C2 C3 C4 112.30(16) . . ?
C2 C3 C13 112.59(16) . . ?
C4 C3 C13 112.97(16) . . ?
C2 C3 H3 106.1 . . ?
C4 C3 H3 106.1 . . ?
C13 C3 H3 106.1 . . ?
F4 C4 C5 108.73(16) . . ?
F4 C4 C3 108.91(15) . . ?
C5 C4 C3 114.46(16) . . ?
F4 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C4 C5 C6 113.51(16) . . ?
C4 C5 C19 111.11(16) . . ?
C6 C5 C19 113.61(16) . . ?
C4 C5 H5 106.0 . . ?
C6 C5 H5 106.0 . . ?
C19 C5 H5 106.0 . . ?
F6 C6 C1 109.33(15) . . ?
F6 C6 C5 109.48(15) . . ?
C1 C6 C5 113.66(16) . . ?
F6 C6 H6 108.1 . . ?
C1 C6 H6 108.1 . . ?
C5 C6 H6 108.1 . . ?
C8 C7 C1 116.51(18) . . ?
C8 C7 H7A 108.2 . . ?
C1 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C1 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C7 C8 C9 111.15(18) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 116.5(2) . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C11 C10 C9 112.8(2) . . ?
C11 C10 C12 109.3(2) . . ?
C9 C10 C12 110.0(2) . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C12 C10 H10 108.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 114.46(17) . . ?
C14 C13 H13A 108.6 . . ?
C3 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C3 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 113.80(19) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 115.1(2) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C18 110.7(2) . . ?
C17 C16 C15 112.5(2) . . ?
C18 C16 C15 111.8(2) . . ?
C17 C16 H16 107.2 . . ?
C18 C16 H16 107.2 . . ?
C15 C16 H16 107.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C5 115.09(17) . . ?
C20 C19 H19A 108.5 . . ?
C5 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C5 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 112.77(18) . . ?
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 . . ?
C22 C21 C20 115.5(2) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C24 111.7(2) . . ?
C21 C22 C23 111.2(2) . . ?
C24 C22 C23 108.8(2) . . ?
C21 C22 H22 108.3 . . ?
C24 C22 H22 108.3 . . ?
C23 C22 H22 108.3 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 -73.8(2) . . . . ?
C7 C1 C2 F2 56.6(2) . . . . ?
C6 C1 C2 C3 47.6(2) . . . . ?
C7 C1 C2 C3 178.02(17) . . . . ?
F2 C2 C3 C4 73.8(2) . . . . ?
C1 C2 C3 C4 -48.0(2) . . . . ?
F2 C2 C3 C13 -55.0(2) . . . . ?
C1 C2 C3 C13 -176.89(17) . . . . ?
C2 C3 C4 F4 -73.6(2) . . . . ?
C13 C3 C4 F4 55.1(2) . . . . ?
C2 C3 C4 C5 48.3(2) . . . . ?
C13 C3 C4 C5 177.00(16) . . . . ?
F4 C4 C5 C6 73.7(2) . . . . ?
C3 C4 C5 C6 -48.3(2) . . . . ?
F4 C4 C5 C19 -55.8(2) . . . . ?
C3 C4 C5 C19 -177.78(16) . . . . ?
C2 C1 C6 F6 76.2(2) . . . . ?
C7 C1 C6 F6 -51.8(2) . . . . ?
C2 C1 C6 C5 -46.4(2) . . . . ?
C7 C1 C6 C5 -174.46(17) . . . . ?
C4 C5 C6 F6 -75.8(2) . . . . ?
C19 C5 C6 F6 52.5(2) . . . . ?
C4 C5 C6 C1 46.8(2) . . . . ?
C19 C5 C6 C1 175.04(16) . . . . ?
C2 C1 C7 C8 171.28(18) . . . . ?
C6 C1 C7 C8 -58.9(3) . . . . ?
C1 C7 C8 C9 -172.21(18) . . . . ?
C7 C8 C9 C10 177.0(2) . . . . ?
C8 C9 C10 C11 61.9(3) . . . . ?
C8 C9 C10 C12 -175.7(2) . . . . ?
C2 C3 C13 C14 -55.2(3) . . . . ?
C4 C3 C13 C14 176.32(17) . . . . ?
C3 C13 C14 C15 -179.91(18) . . . . ?
C13 C14 C15 C16 178.0(2) . . . . ?
C14 C15 C16 C17 56.8(3) . . . . ?
C14 C15 C16 C18 -177.8(2) . . . . ?
C4 C5 C19 C20 -173.79(17) . . . . ?
C6 C5 C19 C20 56.8(3) . . . . ?
C5 C19 C20 C21 176.35(17) . . . . ?
C19 C20 C21 C22 -176.21(19) . . . . ?
C20 C21 C22 C24 -61.3(3) . . . . ?
C20 C21 C22 C23 176.9(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/diethyl ether'
