# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 2068702'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C7 H9 F5'
_chemical_formula_moiety         'C7 H9 F5'
_chemical_formula_weight         188.14
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        C2/m
_space_group_name_Hall           '-C 2y'
_space_group_IT_number           12
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x, y, -z'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
#------------------------------------------------------------------------------
_cell_length_a                   8.3314(3)
_cell_length_b                   7.6652(3)
_cell_length_c                   11.5888(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.667(3)
_cell_angle_gamma                90.0000
_cell_volume                     729.57(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3412
_cell_measurement_theta_min      10.38
_cell_measurement_theta_max      74.99
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.00
_exptl_absorpt_coefficient_mu    1.715
_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  0.695
_exptl_absorpt_correction_T_max  0.842

#==============================================================================
# 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            3739
_diffrn_reflns_av_unetI/netI     0.0069
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_theta_max         75.290
_diffrn_reflns_theta_min         10.448
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             773
_reflns_number_gt                771
_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          0.0342
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0953
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         773
_refine_ls_number_parameters     63
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0464P)²+0.7746P] 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         0.29
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(2)

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 0.43961(9) 0.68625(11) 0.34386(7) 0.0180(3) Uani 1 1 d . . . . .
F3 F 0.35900(10) 0.80800(10) 0.12057(7) 0.0204(3) Uani 1 1 d . . . . .
F4 F 0.52514(12) 0.500000 0.15545(9) 0.0175(3) Uani 1 2 d S T P . .
C1 C 0.2046(2) 0.500000 0.32659(15) 0.0123(4) Uani 1 2 d S T P . .
H1 H 0.086865 0.500000 0.290386 0.015 Uiso 1 2 calc R U P . .
C2 C 0.27902(14) 0.66588(16) 0.28532(11) 0.0132(3) Uani 1 1 d . . . . .
H2 H 0.213231 0.768359 0.303406 0.016 Uiso 1 1 calc R U . . .
C3 C 0.27935(15) 0.66073(16) 0.15451(11) 0.0137(3) Uani 1 1 d . . . . .
H3 H 0.163648 0.664840 0.113806 0.016 Uiso 1 1 calc R U . . .
C4 C 0.3575(2) 0.500000 0.11254(15) 0.0140(4) Uani 1 2 d S T P . .
H4 H 0.339818 0.499999 0.025031 0.017 Uiso 1 2 calc R U P . .
C5 C 0.2114(2) 0.500000 0.45928(16) 0.0168(4) Uani 1 2 d S T P . .
H5A H 0.141701 0.593336 0.480881 0.020 Uiso 0.5 1 calc R U P . .
H5B H 0.323800 0.519389 0.498154 0.020 Uiso 0.5 1 calc R U P . .
H5C H 0.173023 0.387275 0.483852 0.020 Uiso 0.5 1 calc R U P . .


#==============================================================================
_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 1.4035(13) . ?
F3 C3 1.3990(14) . ?
F4 C4 1.4016(19) . ?
C1 C2 1.5263(15) . ?
C1 C2 1.5263(15) 2_565 ?
C1 C5 1.529(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.5170(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5115(16) . ?
C3 H3 1.0000 . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5A 0.98(2) 2_565 ?
C5 H5B 0.980(8) 2_565 ?
C5 H5C 0.980(17) 2_565 ?

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 C2 112.83(14) . 2_565 ?
C2 C1 C5 111.51(9) . . ?
C2 C1 C5 111.52(9) 2_565 . ?
C2 C1 H1 106.9 . . ?
C2 C1 H1 106.9 2_565 . ?
C5 C1 H1 106.9 . . ?
F2 C2 C3 108.93(10) . . ?
F2 C2 C1 110.22(10) . . ?
C3 C2 C1 111.13(11) . . ?
F2 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
F3 C3 C4 108.48(10) . . ?
F3 C3 C2 109.91(10) . . ?
C4 C3 C2 114.58(11) . . ?
F3 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
F4 C4 C3 110.08(9) . 2_565 ?
F4 C4 C3 110.08(9) . . ?
C3 C4 C3 109.19(14) 2_565 . ?
F4 C4 H4 109.2 . . ?
C3 C4 H4 109.2 2_565 . ?
C3 C4 H4 109.2 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C5 H5A 109.5(5) . 2_565 ?
C1 C5 H5B 109.5(2) . 2_565 ?
H5A C5 H5B 109.5 2_565 2_565 ?
C1 C5 H5C 109.5(3) . 2_565 ?
H5A C5 H5C 109.5 2_565 2_565 ?
H5B C5 H5C 109.5 2_565 2_565 ?

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
C2 C1 C2 F2 -70.10(16) 2_565 . . . ?
C5 C1 C2 F2 56.32(15) . . . . ?
C2 C1 C2 C3 50.77(17) 2_565 . . . ?
C5 C1 C2 C3 177.18(11) . . . . ?
F2 C2 C3 F3 -53.98(13) . . . . ?
C1 C2 C3 F3 -175.60(10) . . . . ?
F2 C2 C3 C4 68.45(13) . . . . ?
C1 C2 C3 C4 -53.17(15) . . . . ?
F3 C3 C4 F4 55.81(14) . . . . ?
C2 C3 C4 F4 -67.39(14) . . . . ?
F3 C3 C4 C3 176.76(8) . . . 2_565 ?
C2 C3 C4 C3 53.56(18) . . . 2_565 ?


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


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

data_5
_database_code_depnum_ccdc_archive 'CCDC 2068704'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 F10'
_chemical_formula_sum            'C14 H16 F10'
_chemical_formula_weight         374.27
_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/c
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3268(9)
_cell_length_b                   11.8350(16)
_cell_length_c                   9.9391(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.293(16)
_cell_angle_gamma                90
_cell_volume                     724.28(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1062
_cell_measurement_temperature    173
_cell_measurement_theta_max      63.8570
_cell_measurement_theta_min      5.9160
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08312
_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    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1814
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7216
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         5.908
_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 0.993
_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   40.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50   40.00    --  -30.00 -72.00 -90.00  146
  3  ω   -113.00 -71.00   0.50   40.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50   40.00   0.00 -67.00   0.00    --   400
  5  ω    -85.00 -13.00   0.50   40.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50   40.00    --  -67.00 180.00   0.00   80
  7  ω    -85.00 -12.00   0.50   40.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50   40.00    --  -67.00 180.00-180.00   80
  9  φ      0.00 200.00   0.50   40.00 -25.00-110.00   0.00    --   400
 10  ω   -128.00 -20.00   0.50   40.00    -- -110.00  72.00-135.00  216
 11  ω   -128.00 -20.00   0.50   40.00    -- -110.00  72.00  45.00  216
 12  ω   -115.00 -20.00   0.50   40.00    -- -110.00  72.00 -45.00  190
 13  ω   -113.00 -23.00   0.50   40.00    -- -110.00  72.00 135.00  180
 14  ω   -141.00 -46.00   0.50   40.00    -- -110.00 180.00 -90.00  190
 15  ω   -141.00 -46.00   0.50   40.00    -- -110.00 180.00-180.00  190
 16  ω   -141.00 -59.00   0.50   40.00    -- -110.00 180.00  90.00  164
 17  ω   -141.00 -55.00   0.50   40.00    -- -110.00 180.00   0.00  172
 18  ω   -141.00 -59.00   0.50   40.00    -- -110.00 180.00  45.00  164
 19  ω   -141.00 -78.00   0.50   40.00    -- -110.00 180.00 -45.00  126
 20  ω   -140.00 -77.00   0.50   40.00    -- -110.00 180.00-135.00  126
 21  ω   -140.00 -56.00   0.50   40.00    -- -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      0.0687687000
_diffrn_orient_matrix_UB_12      -0.0932125000
_diffrn_orient_matrix_UB_13      0.1092692000
_diffrn_orient_matrix_UB_21      0.2103266000
_diffrn_orient_matrix_UB_22      -0.0186772000
_diffrn_orient_matrix_UB_23      -0.0504482000
_diffrn_orient_matrix_UB_31      0.1170426000
_diffrn_orient_matrix_UB_32      0.0887019000
_diffrn_orient_matrix_UB_33      0.1043958000
_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                477
_reflns_number_total             1318
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       0.066(15)
_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   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2141
_refine_ls_R_factor_gt           0.1179
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2865
_refine_ls_wR_factor_ref         0.3811
_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)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
;
_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 0.4729(8) 0.6539(4) 0.4562(6) 0.1066(19) Uani 1 1 d . . . . .
F3 F 0.6385(9) 0.8306(5) 0.6268(6) 0.123(2) Uani 1 1 d . . . . .
F4 F 0.3703(8) 0.8749(4) 0.3774(5) 0.107(2) Uani 1 1 d . . . . .
F5 F -0.0649(8) 0.9143(4) 0.3593(5) 0.113(2) Uani 1 1 d . . . . .
F6 F 0.0595(8) 0.7012(4) 0.3023(5) 0.1014(18) Uani 1 1 d . . . . .
C1 C 0.1435(13) 0.6471(7) 0.5386(10) 0.093(3) Uani 1 1 d . . . . .
H1 H 0.092677 0.658836 0.625698 0.111 Uiso 1 1 calc R U . . .
C2 C 0.3876(13) 0.6782(7) 0.5713(9) 0.090(3) Uani 1 1 d . . . . .
H2 H 0.466515 0.632684 0.652170 0.109 Uiso 1 1 calc R U . . .
C3 C 0.4163(14) 0.8032(8) 0.6060(11) 0.102(3) Uani 1 1 d . . . . .
H3 H 0.370136 0.817113 0.694232 0.122 Uiso 1 1 calc R U . . .
C4 C 0.2907(14) 0.8802(8) 0.4980(9) 0.096(3) Uani 1 1 d . . . . .
H4 H 0.304617 0.959369 0.534019 0.115 Uiso 1 1 calc R U . . .
C5 C 0.0538(13) 0.8454(7) 0.4676(9) 0.089(3) Uani 1 1 d . . . . .
H5 H -0.001600 0.861180 0.552148 0.107 Uiso 1 1 calc R U . . .
C6 C 0.0090(13) 0.7245(7) 0.4305(9) 0.086(2) Uani 1 1 d . . . . .
H6 H -0.148591 0.708827 0.423162 0.103 Uiso 1 1 calc R U . . .
C7 C 0.1175(12) 0.5194(7) 0.5040(9) 0.091(3) Uani 1 1 d . . . . .
H7A H 0.155753 0.504820 0.414466 0.109 Uiso 1 1 calc R U . . .
H7B H 0.218159 0.475442 0.576175 0.109 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 1.403(9) . ?
F3 C3 1.411(9) . ?
F4 C4 1.404(8) . ?
F5 C5 1.419(9) . ?
F6 C6 1.410(8) . ?
C1 H1 1.0000 . ?
C1 C2 1.548(11) . ?
C1 C6 1.517(11) . ?
C1 C7 1.550(11) . ?
C2 H2 1.0000 . ?
C2 C3 1.520(12) . ?
C3 H3 1.0000 . ?
C3 C4 1.490(12) . ?
C4 H4 1.0000 . ?
C4 C5 1.516(11) . ?
C5 H5 1.0000 . ?
C5 C6 1.488(11) . ?
C6 H6 1.0000 . ?
C7 C7 1.540(14) 3_566 ?
C7 H7A 0.9900 . ?
C7 H7B 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
C2 C1 H1 106.8 . . ?
C2 C1 C7 109.2(6) . . ?
C6 C1 H1 106.8 . . ?
C6 C1 C2 112.1(7) . . ?
C6 C1 C7 114.8(8) . . ?
C7 C1 H1 106.8 . . ?
F2 C2 C1 109.4(7) . . ?
F2 C2 H2 109.3 . . ?
F2 C2 C3 109.6(7) . . ?
C1 C2 H2 109.3 . . ?
C3 C2 C1 109.9(7) . . ?
C3 C2 H2 109.3 . . ?
F3 C3 C2 108.7(7) . . ?
F3 C3 H3 108.4 . . ?
F3 C3 C4 108.3(7) . . ?
C2 C3 H3 108.4 . . ?
C4 C3 C2 114.6(8) . . ?
C4 C3 H3 108.4 . . ?
F4 C4 C3 110.6(7) . . ?
F4 C4 H4 109.1 . . ?
F4 C4 C5 110.5(7) . . ?
C3 C4 H4 109.1 . . ?
C3 C4 C5 108.5(7) . . ?
C5 C4 H4 109.1 . . ?
F5 C5 C4 108.8(7) . . ?
F5 C5 H5 107.7 . . ?
F5 C5 C6 109.1(7) . . ?
C4 C5 H5 107.7 . . ?
C6 C5 C4 115.7(7) . . ?
C6 C5 H5 107.7 . . ?
F6 C6 C1 108.3(6) . . ?
F6 C6 C5 110.0(6) . . ?
F6 C6 H6 109.1 . . ?
C1 C6 H6 109.1 . . ?
C5 C6 C1 111.2(7) . . ?
C5 C6 H6 109.1 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C7 C7 C1 110.7(8) 3_566 . ?
C7 C7 H7A 109.5 3_566 . ?
C7 C7 H7B 109.5 3_566 . ?
H7A C7 H7B 108.1 . . ?

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 -56.1(10) . . . . ?
F2 C2 C3 C4 65.1(8) . . . . ?
F3 C3 C4 F4 54.6(9) . . . . ?
F3 C3 C4 C5 175.9(7) . . . . ?
F4 C4 C5 F5 -55.4(9) . . . . ?
F4 C4 C5 C6 67.7(9) . . . . ?
F5 C5 C6 F6 56.2(8) . . . . ?
F5 C5 C6 C1 176.3(7) . . . . ?
C1 C2 C3 F3 -176.4(7) . . . . ?
C1 C2 C3 C4 -55.1(10) . . . . ?
C2 C1 C6 F6 69.7(9) . . . . ?
C2 C1 C6 C5 -51.2(10) . . . . ?
C2 C1 C7 C7 170.1(9) . . . 3_566 ?
C2 C3 C4 F4 -66.9(9) . . . . ?
C2 C3 C4 C5 54.4(10) . . . . ?
C3 C4 C5 F5 -176.8(7) . . . . ?
C3 C4 C5 C6 -53.6(10) . . . . ?
C4 C5 C6 F6 -66.8(9) . . . . ?
C4 C5 C6 C1 53.2(10) . . . . ?
C6 C1 C2 F2 -68.5(9) . . . . ?
C6 C1 C2 C3 51.9(10) . . . . ?
C6 C1 C7 C7 -63.2(11) . . . 3_566 ?
C7 C1 C2 F2 59.7(8) . . . . ?
C7 C1 C2 C3 -179.8(8) . . . . ?
C7 C1 C6 F6 -55.5(8) . . . . ?
C7 C1 C6 C5 -176.5(6) . . . . ?

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 2068703'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C8 H11 F5'
_chemical_formula_moiety         'C8 H11 F5'
_chemical_formula_weight         202.17
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        Pbca
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   15.594(7)
_cell_length_b                   12.835(7)
_cell_length_c                   8.557(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1712.7(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2363
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.10
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832.00
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.998

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            18234
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_theta_max         25.445
_diffrn_reflns_theta_min         3.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1575
_reflns_number_gt                1115
_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          0.0684
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1316
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1575
_refine_ls_number_parameters     119
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0964P)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         0.41
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.26631(9) 0.68428(11) 0.21063(14) 0.0281(4) Uani 1 1 d . . . . .
F3 F 0.12594(9) 0.79382(11) 0.29728(15) 0.0308(4) Uani 1 1 d . . . . .
F4 F 0.10760(10) 0.58722(11) 0.22659(15) 0.0319(4) Uani 1 1 d . . . . .
F5 F 0.09680(10) 0.44465(10) 0.46784(18) 0.0363(4) Uani 1 1 d . . . . .
F6 F 0.24692(9) 0.46991(10) 0.30998(15) 0.0289(4) Uani 1 1 d . . . . .
C1 C 0.29035(16) 0.61531(18) 0.4686(3) 0.0247(6) Uani 1 1 d . . . . .
H1 H 0.287682 0.638585 0.579981 0.030 Uiso 1 1 calc R U . . .
C2 C 0.25301(16) 0.70433(18) 0.3713(3) 0.0252(6) Uani 1 1 d . . . . .
H2 H 0.283376 0.770299 0.399651 0.030 Uiso 1 1 calc R U . . .
C3 C 0.15862(16) 0.71869(17) 0.3998(3) 0.0266(6) Uani 1 1 d . . . . .
H3 H 0.151054 0.745097 0.508845 0.032 Uiso 1 1 calc R U . . .
C4 C 0.10581(16) 0.62014(18) 0.3827(3) 0.0263(6) Uani 1 1 d . . . . .
H4 H 0.045269 0.634148 0.415009 0.032 Uiso 1 1 calc R U . . .
C5 C 0.14405(16) 0.53692(18) 0.4869(3) 0.0281(6) Uani 1 1 d . . . . .
H5 H 0.137369 0.560168 0.597802 0.034 Uiso 1 1 calc R U . . .
C6 C 0.23727(16) 0.51591(18) 0.4588(3) 0.0264(6) Uani 1 1 d . . . . .
H6 H 0.258269 0.465886 0.539815 0.032 Uiso 1 1 calc R U . . .
C7 C 0.38473(16) 0.59508(19) 0.4332(3) 0.0285(6) Uani 1 1 d . . . . .
H7A H 0.402699 0.530209 0.486569 0.034 Uiso 1 1 calc R U . . .
H7B H 0.391718 0.584332 0.319387 0.034 Uiso 1 1 calc R U . . .
C8 C 0.44296(17) 0.6836(2) 0.4850(4) 0.0431(7) Uani 1 1 d . . . . .
H8A H 0.502841 0.664723 0.464787 0.052 Uiso 1 1 calc R U . . .
H8B H 0.435050 0.696203 0.597017 0.052 Uiso 1 1 calc R U . . .
H8C H 0.428531 0.746849 0.426533 0.052 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    '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 1.414(3) . ?
F3 C3 1.399(3) . ?
F4 C4 1.402(3) . ?
F5 C5 1.404(3) . ?
F6 C6 1.412(3) . ?
C1 C6 1.523(3) . ?
C1 C7 1.525(4) . ?
C1 C2 1.529(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.503(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.516(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.514(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.498(4) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C7 111.8(2) . . ?
C6 C1 C2 112.9(2) . . ?
C7 C1 C2 112.8(2) . . ?
C6 C1 H1 106.3 . . ?
C7 C1 H1 106.3 . . ?
C2 C1 H1 106.3 . . ?
F2 C2 C3 108.87(19) . . ?
F2 C2 C1 109.72(18) . . ?
C3 C2 C1 112.11(19) . . ?
F2 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
F3 C3 C2 109.85(19) . . ?
F3 C3 C4 108.47(18) . . ?
C2 C3 C4 114.5(2) . . ?
F3 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
F4 C4 C5 109.93(19) . . ?
F4 C4 C3 109.40(18) . . ?
C5 C4 C3 108.55(19) . . ?
F4 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
F5 C5 C6 109.80(19) . . ?
F5 C5 C4 108.66(19) . . ?
C6 C5 C4 114.5(2) . . ?
F5 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
F6 C6 C5 108.88(19) . . ?
F6 C6 C1 110.00(18) . . ?
C5 C6 C1 111.6(2) . . ?
F6 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
C1 C6 H6 108.8 . . ?
C8 C7 C1 113.1(2) . . ?
C8 C7 H7A 109.0 . . ?
C1 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 -72.7(2) . . . . ?
C7 C1 C2 F2 55.2(3) . . . . ?
C6 C1 C2 C3 48.4(3) . . . . ?
C7 C1 C2 C3 176.26(19) . . . . ?
F2 C2 C3 F3 -52.6(2) . . . . ?
C1 C2 C3 F3 -174.21(17) . . . . ?
F2 C2 C3 C4 69.7(2) . . . . ?
C1 C2 C3 C4 -51.9(3) . . . . ?
F3 C3 C4 F4 57.0(2) . . . . ?
C2 C3 C4 F4 -66.1(2) . . . . ?
F3 C3 C4 C5 176.93(19) . . . . ?
C2 C3 C4 C5 53.9(3) . . . . ?
F4 C4 C5 F5 -58.6(2) . . . . ?
C3 C4 C5 F5 -178.26(18) . . . . ?
F4 C4 C5 C6 64.5(3) . . . . ?
C3 C4 C5 C6 -55.1(3) . . . . ?
F5 C5 C6 F6 54.9(2) . . . . ?
C4 C5 C6 F6 -67.6(2) . . . . ?
F5 C5 C6 C1 176.54(18) . . . . ?
C4 C5 C6 C1 54.0(3) . . . . ?
C7 C1 C6 F6 -56.7(2) . . . . ?
C2 C1 C6 F6 71.8(2) . . . . ?
C7 C1 C6 C5 -177.60(19) . . . . ?
C2 C1 C6 C5 -49.2(3) . . . . ?
C6 C1 C7 C8 -164.0(2) . . . . ?
C2 C1 C7 C8 67.6(3) . . . . ?


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


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

data_6
_database_code_depnum_ccdc_archive 'CCDC 2068705'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           'by CrystalStructure 4.3'

# start Validation Reply Form
_vrf_PLAT084_6                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.52 Report
RESPONSE: poor quality crystal
;

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

_chemical_formula_sum            'C24 H36 F10'
_chemical_formula_moiety         'C24 H36 F10'
_chemical_formula_weight         514.53
_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                   18.982(6)
_cell_length_b                   5.1880(10)
_cell_length_c                   12.315(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.79(2)
_cell_angle_gamma                90.0000
_cell_volume                     1201.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1590
_cell_measurement_theta_min      7.95
_cell_measurement_theta_max      66.72
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540.00
_exptl_absorpt_coefficient_mu    1.193
_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  0.558
_exptl_absorpt_correction_T_max  0.988

#==============================================================================
# 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            11100
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_theta_max         69.622
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2183
_reflns_number_gt                1090
_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).

    Refined as a 2-component twin.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2101
_refine_ls_R_factor_gt           0.1661
_refine_ls_wR_factor_ref         0.5161
_refine_ls_wR_factor_gt          0.4847
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2183
_refine_ls_number_parameters     155
_refine_ls_goodness_of_fit_ref   1.723
_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         0.67
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2706(4) 0.6990(17) 0.7345(6) 0.160(3) Uani 1 1 d . . . . .
F2 F 0.3373(4) 0.8840(10) 0.5667(5) 0.131(2) Uani 1 1 d . . . . .
F3 F 0.4719(4) 0.6912(18) 0.5745(6) 0.156(3) Uani 1 1 d . . . . .
F4 F 0.4164(3) 0.7680(10) 0.7636(4) 0.1065(19) Uani 1 1 d . . . . .
F5 F 0.3573(4) 0.3619(13) 0.8611(5) 0.131(2) Uani 1 1 d . . . . .
C1 C 0.2842(4) 0.4686(16) 0.5685(7) 0.082(2) Uani 1 1 d . . . . .
H1 H 0.290721 0.288234 0.543059 0.098 Uiso 1 1 calc R U . . .
C2 C 0.3475(5) 0.6267(17) 0.5391(7) 0.091(2) Uani 1 1 d . . . . .
H2 H 0.348083 0.615446 0.458208 0.109 Uiso 1 1 calc R U . . .
C3 C 0.4172(5) 0.535(2) 0.5958(8) 0.102(3) Uani 1 1 d . . . . .
H3 H 0.425925 0.358240 0.567663 0.123 Uiso 1 1 calc R U . . .
C4 C 0.4183(5) 0.5162(15) 0.7219(7) 0.085(2) Uani 1 1 d . . . . .
H4 H 0.463347 0.430628 0.754772 0.102 Uiso 1 1 calc R U . . .
C5 C 0.3572(5) 0.362(2) 0.7473(7) 0.098(3) Uani 1 1 d . . . . .
H5 H 0.363428 0.180596 0.722825 0.118 Uiso 1 1 calc R U . . .
C6 C 0.2859(6) 0.457(2) 0.6947(8) 0.106(3) Uani 1 1 d . . . . .
H6 H 0.248595 0.333373 0.711913 0.128 Uiso 1 1 calc R U . . .
C7 C 0.2110(5) 0.5614(19) 0.5123(7) 0.100(3) Uani 1 1 d . . . . .
H7A H 0.173673 0.502845 0.555536 0.120 Uiso 1 1 calc R U . . .
H7B H 0.210258 0.752144 0.510743 0.120 Uiso 1 1 calc R U . . .
C8 C 0.1946(4) 0.4606(17) 0.3972(7) 0.088(2) Uani 1 1 d . . . . .
H8A H 0.191085 0.270383 0.399916 0.106 Uiso 1 1 calc R U . . .
H8B H 0.234702 0.503775 0.356735 0.106 Uiso 1 1 calc R U . . .
C9 C 0.1269(5) 0.5657(18) 0.3345(7) 0.093(3) Uani 1 1 d . . . . .
H9A H 0.130254 0.755870 0.330966 0.112 Uiso 1 1 calc R U . . .
H9B H 0.086549 0.522621 0.374471 0.112 Uiso 1 1 calc R U . . .
C10 C 0.1120(5) 0.4587(18) 0.2183(7) 0.088(2) Uani 1 1 d . . . . .
H10A H 0.153742 0.494324 0.180532 0.105 Uiso 1 1 calc R U . . .
H10B H 0.107107 0.269131 0.222971 0.105 Uiso 1 1 calc R U . . .
C11 C 0.0462(4) 0.5642(16) 0.1483(7) 0.084(2) Uani 1 1 d . . . . .
H11A H 0.004283 0.532026 0.186280 0.101 Uiso 1 1 calc R U . . .
H11B H 0.051377 0.753082 0.141313 0.101 Uiso 1 1 calc R U . . .
C12 C 0.0326(4) 0.4475(16) 0.0348(6) 0.082(2) Uani 1 1 d . . . . .
H12A H 0.074553 0.479391 -0.003197 0.099 Uiso 1 1 calc R U . . .
H12B H 0.027370 0.258552 0.041737 0.099 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
F1 C6 1.390(12) . ?
F2 C2 1.397(10) . ?
F3 C3 1.372(10) . ?
F4 C4 1.406(8) . ?
F5 C5 1.401(10) . ?
C1 C2 1.537(12) . ?
C1 C7 1.544(11) . ?
C1 C6 1.551(12) . ?
C1 H1 1.0000 . ?
C2 C3 1.489(13) . ?
C2 H2 1.0000 . ?
C3 C4 1.553(12) . ?
C3 H3 1.0000 . ?
C4 C5 1.477(13) . ?
C4 H4 1.0000 . ?
C5 C6 1.503(13) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.503(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.509(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C12 1.509(14) 3_565 ?
C12 H12A 0.9900 . ?
C12 H12B 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
C2 C1 C7 114.4(7) . . ?
C2 C1 C6 110.2(7) . . ?
C7 C1 C6 110.8(8) . . ?
C2 C1 H1 107.0 . . ?
C7 C1 H1 107.0 . . ?
C6 C1 H1 107.0 . . ?
F2 C2 C3 109.6(8) . . ?
F2 C2 C1 108.4(8) . . ?
C3 C2 C1 113.0(7) . . ?
F2 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
F3 C3 C2 111.6(9) . . ?
F3 C3 C4 108.6(8) . . ?
C2 C3 C4 112.3(8) . . ?
F3 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
F4 C4 C5 111.5(8) . . ?
F4 C4 C3 108.1(7) . . ?
C5 C4 C3 109.9(7) . . ?
F4 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
F5 C5 C4 108.5(8) . . ?
F5 C5 C6 108.1(9) . . ?
C4 C5 C6 114.7(8) . . ?
F5 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
F1 C6 C5 111.3(8) . . ?
F1 C6 C1 110.0(8) . . ?
C5 C6 C1 109.8(9) . . ?
F1 C6 H6 108.6 . . ?
C5 C6 H6 108.6 . . ?
C1 C6 H6 108.6 . . ?
C8 C7 C1 111.9(7) . . ?
C8 C7 H7A 109.2 . . ?
C1 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 114.2(8) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 112.7(8) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 115.8(8) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 113.8(7) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C12 C11 113.8(9) 3_565 . ?
C12 C12 H12A 108.8 3_565 . ?
C11 C12 H12A 108.8 . . ?
C12 C12 H12B 108.8 3_565 . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 57.6(9) . . . . ?
C6 C1 C2 F2 -68.1(9) . . . . ?
C7 C1 C2 C3 179.3(7) . . . . ?
C6 C1 C2 C3 53.6(10) . . . . ?
F2 C2 C3 F3 -54.3(10) . . . . ?
C1 C2 C3 F3 -175.3(7) . . . . ?
F2 C2 C3 C4 67.9(10) . . . . ?
C1 C2 C3 C4 -53.1(10) . . . . ?
F3 C3 C4 F4 54.5(10) . . . . ?
C2 C3 C4 F4 -69.4(10) . . . . ?
F3 C3 C4 C5 176.4(8) . . . . ?
C2 C3 C4 C5 52.5(11) . . . . ?
F4 C4 C5 F5 -56.6(10) . . . . ?
C3 C4 C5 F5 -176.5(8) . . . . ?
F4 C4 C5 C6 64.3(10) . . . . ?
C3 C4 C5 C6 -55.6(11) . . . . ?
F5 C5 C6 F1 56.2(11) . . . . ?
C4 C5 C6 F1 -65.0(11) . . . . ?
F5 C5 C6 C1 178.2(8) . . . . ?
C4 C5 C6 C1 57.1(11) . . . . ?
C2 C1 C6 F1 69.4(10) . . . . ?
C7 C1 C6 F1 -58.3(11) . . . . ?
C2 C1 C6 C5 -53.4(11) . . . . ?
C7 C1 C6 C5 178.9(8) . . . . ?
C2 C1 C7 C8 81.7(10) . . . . ?
C6 C1 C7 C8 -153.0(9) . . . . ?
C1 C7 C8 C9 -174.4(8) . . . . ?
C7 C8 C9 C10 -179.9(8) . . . . ?
C8 C9 C10 C11 -177.5(7) . . . . ?
C9 C10 C11 C12 -178.6(8) . . . . ?
C10 C11 C12 C12 -179.9(9) . . . 3_565 ?


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


####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2068707'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C19 H33 F5'
_chemical_formula_moiety         'C19 H33 F5'
_chemical_formula_weight         356.46
_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                   5.64684(18)
_cell_length_b                   5.62268(14)
_cell_length_c                   30.1035(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.117(3)
_cell_angle_gamma                90.0000
_cell_volume                     951.99(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5218
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      67.78
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.00
_exptl_absorpt_coefficient_mu    0.887
_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  0.757
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# 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            12752
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_theta_max         68.261
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3392
_reflns_number_gt                3004
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.950

#==============================================================================
# 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          0.0476
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1206
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3392
_refine_ls_number_parameters     218
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0678P)²+0.1855P] 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         0.25
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(8)

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 -0.2209(4) 1.6718(3) 0.38474(7) 0.0477(5) Uani 1 1 d . . . . .
F3 F -0.0591(4) 1.6233(4) 0.47156(7) 0.0567(6) Uani 1 1 d . . . . .
F4 F -0.5253(3) 1.5181(3) 0.44777(7) 0.0466(5) Uani 1 1 d . . . . .
F5 F -0.6581(3) 1.0517(4) 0.43359(7) 0.0521(5) Uani 1 1 d . . . . .
F6 F -0.5880(3) 1.3284(4) 0.36180(6) 0.0462(5) Uani 1 1 d . . . . .
C1 C -0.1666(5) 1.2617(6) 0.36792(10) 0.0355(7) Uani 1 1 d . . . . .
H1 H -0.048956 1.130443 0.374377 0.043 Uiso 1 1 calc R U . . .
C2 C -0.0876(5) 1.4689(6) 0.39796(11) 0.0388(7) Uani 1 1 d . . . . .
H2 H 0.083794 1.502163 0.394516 0.047 Uiso 1 1 calc R U . . .
C3 C -0.1147(6) 1.4193(6) 0.44644(11) 0.0426(8) Uani 1 1 d . . . . .
H3 H 0.002482 1.292949 0.456632 0.051 Uiso 1 1 calc R U . . .
C4 C -0.3603(6) 1.3341(6) 0.45613(11) 0.0398(7) Uani 1 1 d . . . . .
H4 H -0.357027 1.284526 0.488087 0.048 Uiso 1 1 calc R U . . .
C5 C -0.4258(5) 1.1240(6) 0.42651(11) 0.0405(8) Uani 1 1 d . . . . .
H5 H -0.315321 0.990595 0.435916 0.049 Uiso 1 1 calc R U . . .
C6 C -0.4119(5) 1.1647(6) 0.37741(11) 0.0375(7) Uani 1 1 d . . . . .
H6 H -0.440622 1.010585 0.361244 0.045 Uiso 1 1 calc R U . . .
C7 C -0.1573(6) 1.3308(7) 0.31905(11) 0.0416(8) Uani 1 1 d . . . . .
H7A H -0.285964 1.447052 0.311217 0.050 Uiso 1 1 calc R U . . .
H7B H -0.004500 1.413095 0.316109 0.050 Uiso 1 1 calc R U . . .
C8 C -0.1808(6) 1.1306(7) 0.28500(11) 0.0452(8) Uani 1 1 d . . . . .
H8A H -0.219517 1.201534 0.255134 0.054 Uiso 1 1 calc R U . . .
H8B H -0.317185 1.029749 0.291531 0.054 Uiso 1 1 calc R U . . .
C9 C 0.0360(6) 0.9710(7) 0.28291(11) 0.0430(8) Uani 1 1 d . . . . .
H9A H 0.179566 1.070844 0.281589 0.052 Uiso 1 1 calc R U . . .
H9B H 0.057365 0.873164 0.310317 0.052 Uiso 1 1 calc R U . . .
C10 C 0.0089(6) 0.8089(7) 0.24239(11) 0.0433(8) Uani 1 1 d . . . . .
H10A H -0.132036 0.706668 0.244847 0.052 Uiso 1 1 calc R U . . .
H10B H -0.024054 0.909258 0.215523 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2191(6) 0.6497(7) 0.23520(11) 0.0435(8) Uani 1 1 d . . . . .
H11A H 0.249427 0.543004 0.261251 0.052 Uiso 1 1 calc R U . . .
H11B H 0.362217 0.749534 0.233258 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1789(6) 0.4992(7) 0.19295(12) 0.0449(8) Uani 1 1 d . . . . .
H12A H 0.031379 0.405567 0.194457 0.054 Uiso 1 1 calc R U . . .
H12B H 0.154234 0.606969 0.166940 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3803(6) 0.3302(7) 0.18537(11) 0.0448(8) Uani 1 1 d . . . . .
H13A H 0.401813 0.218936 0.210891 0.054 Uiso 1 1 calc R U . . .
H13B H 0.528881 0.423041 0.184695 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3410(6) 0.1871(7) 0.14257(12) 0.0458(8) Uani 1 1 d . . . . .
H14A H 0.321426 0.298287 0.117018 0.055 Uiso 1 1 calc R U . . .
H14B H 0.191450 0.095668 0.143085 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5426(6) 0.0150(7) 0.13527(12) 0.0464(8) Uani 1 1 d . . . . .
H15A H 0.692405 0.106310 0.134990 0.056 Uiso 1 1 calc R U . . .
H15B H 0.561487 -0.096873 0.160737 0.056 Uiso 1 1 calc R U . . .
C16 C 0.5048(6) -0.1269(7) 0.09245(12) 0.0463(8) Uani 1 1 d . . . . .
H16A H 0.486656 -0.015197 0.066943 0.056 Uiso 1 1 calc R U . . .
H16B H 0.354853 -0.217997 0.092658 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7073(6) -0.2994(7) 0.08549(12) 0.0463(8) Uani 1 1 d . . . . .
H17A H 0.857354 -0.208250 0.085552 0.056 Uiso 1 1 calc R U . . .
H17B H 0.724602 -0.411601 0.110924 0.056 Uiso 1 1 calc R U . . .
C18 C 0.6718(7) -0.4406(8) 0.04263(13) 0.0546(10) Uani 1 1 d . . . . .
H18A H 0.661077 -0.328848 0.017118 0.065 Uiso 1 1 calc R U . . .
H18B H 0.518800 -0.527043 0.042009 0.065 Uiso 1 1 calc R U . . .
C19 C 0.8700(7) -0.6190(8) 0.03681(14) 0.0593(11) Uani 1 1 d . . . . .
H19A H 0.868593 -0.742642 0.059736 0.071 Uiso 1 1 calc R U . . .
H19B H 1.023758 -0.536993 0.039743 0.071 Uiso 1 1 calc R U . . .
H19C H 0.845159 -0.692146 0.007210 0.071 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    'SIR2004 (Burla, et al., 2005)'
_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 1.405(4) . ?
F3 C3 1.395(4) . ?
F4 C4 1.400(4) . ?
F5 C5 1.408(4) . ?
F6 C6 1.405(3) . ?
C1 C2 1.517(4) . ?
C1 C7 1.527(5) . ?
C1 C6 1.539(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.507(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.520(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.506(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.505(5) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.520(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.528(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.529(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.525(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 C7 110.2(3) . . ?
C2 C1 C6 112.5(2) . . ?
C7 C1 C6 112.2(3) . . ?
C2 C1 H1 107.2 . . ?
C7 C1 H1 107.2 . . ?
C6 C1 H1 107.2 . . ?
F2 C2 C3 109.1(2) . . ?
F2 C2 C1 109.5(2) . . ?
C3 C2 C1 112.7(3) . . ?
F2 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
F3 C3 C2 109.6(3) . . ?
F3 C3 C4 108.7(3) . . ?
C2 C3 C4 114.7(3) . . ?
F3 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
F4 C4 C5 110.4(2) . . ?
F4 C4 C3 109.7(3) . . ?
C5 C4 C3 108.3(3) . . ?
F4 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
F5 C5 C6 108.9(3) . . ?
F5 C5 C4 108.6(3) . . ?
C6 C5 C4 115.5(3) . . ?
F5 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
F6 C6 C5 109.3(2) . . ?
F6 C6 C1 109.1(3) . . ?
C5 C6 C1 111.3(2) . . ?
F6 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
C1 C6 H6 109.0 . . ?
C8 C7 C1 116.9(3) . . ?
C8 C7 H7A 108.1 . . ?
C1 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C7 C8 C9 116.2(3) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 111.3(3) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 116.4(3) . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C9 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C10 C11 C12 112.7(3) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 114.5(3) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 113.9(3) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.9(3) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 114.0(3) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.6(3) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.9(3) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 113.6(3) . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C7 C1 C2 F2 53.1(3) . . . . ?
C6 C1 C2 F2 -72.9(3) . . . . ?
C7 C1 C2 C3 174.6(3) . . . . ?
C6 C1 C2 C3 48.6(3) . . . . ?
F2 C2 C3 F3 -53.1(3) . . . . ?
C1 C2 C3 F3 -174.8(2) . . . . ?
F2 C2 C3 C4 69.5(4) . . . . ?
C1 C2 C3 C4 -52.3(4) . . . . ?
F3 C3 C4 F4 55.6(3) . . . . ?
C2 C3 C4 F4 -67.5(3) . . . . ?
F3 C3 C4 C5 176.1(2) . . . . ?
C2 C3 C4 C5 53.1(4) . . . . ?
F4 C4 C5 F5 -56.9(3) . . . . ?
C3 C4 C5 F5 -177.0(3) . . . . ?
F4 C4 C5 C6 65.7(3) . . . . ?
C3 C4 C5 C6 -54.3(4) . . . . ?
F5 C5 C6 F6 55.3(3) . . . . ?
C4 C5 C6 F6 -67.2(3) . . . . ?
F5 C5 C6 C1 175.9(2) . . . . ?
C4 C5 C6 C1 53.4(3) . . . . ?
C2 C1 C6 F6 72.1(3) . . . . ?
C7 C1 C6 F6 -52.8(3) . . . . ?
C2 C1 C6 C5 -48.6(3) . . . . ?
C7 C1 C6 C5 -173.5(3) . . . . ?
C2 C1 C7 C8 167.7(3) . . . . ?
C6 C1 C7 C8 -66.1(3) . . . . ?
C1 C7 C8 C9 -74.5(4) . . . . ?
C7 C8 C9 C10 -169.4(3) . . . . ?
C8 C9 C10 C11 177.0(3) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C10 C11 C12 C13 -177.7(3) . . . . ?
C11 C12 C13 C14 -178.3(3) . . . . ?
C12 C13 C14 C15 -179.3(3) . . . . ?
C13 C14 C15 C16 -179.6(3) . . . . ?
C14 C15 C16 C17 -179.8(3) . . . . ?
C15 C16 C17 C18 -179.6(3) . . . . ?
C16 C17 C18 C19 -177.8(3) . . . . ?


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


####################################################################### 
# 
# 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 2068706'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-06-23 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           'by CrystalStructure 4.3'

# start Validation Reply Form
_vrf_PLAT084_8                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.49 Report
RESPONSE: poor quality crystals
;

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

_chemical_formula_sum            'C19 H33 F5 O'
_chemical_formula_moiety         'C19 H33 F5 O'
_chemical_formula_weight         372.46
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.5481(6)
_cell_length_b                   5.5766(6)
_cell_length_c                   62.078(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1920.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4236
_cell_measurement_theta_min      7.99
_cell_measurement_theta_max      72.72
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800.00
_exptl_absorpt_coefficient_mu    0.943
_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  0.489
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# 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            21334
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.2214
_diffrn_reflns_theta_max         77.910
_diffrn_reflns_theta_min         2.847
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -77
_diffrn_reflns_limit_l_max       76
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3910
_reflns_number_gt                2746
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.991

#==============================================================================
# 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 two-component twin.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2012
_refine_ls_R_factor_gt           0.1806
_refine_ls_wR_factor_ref         0.4893
_refine_ls_wR_factor_gt          0.4689
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3910
_refine_ls_number_parameters     231
_refine_ls_goodness_of_fit_ref   1.809
_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         0.67
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 1.0272(10) 0.9106(14) 0.68321(12) 0.0776(19) Uani 1 1 d . . . . .
F3 F 1.1347(12) 0.6271(14) 0.71792(14) 0.091(2) Uani 1 1 d . . . . .
F4 F 1.0059(11) 1.0987(12) 0.72505(12) 0.0780(19) Uani 1 1 d . . . . .
F5 F 0.5466(12) 1.2098(16) 0.73619(14) 0.093(2) Uani 1 1 d . . . . .
F6 F 0.6725(12) 1.2559(14) 0.69419(12) 0.084(2) Uani 1 1 d . . . . .
O20 O -0.546(3) -1.179(2) 0.50533(18) 0.110(4) Uani 1 1 d D . . . .
H20 H -0.45(2) -1.323(17) 0.508(2) 0.09(5) Uiso 1 1 d D . . . .
C1 C 0.6041(19) 0.840(2) 0.6859(2) 0.072(3) Uani 1 1 d . . . . .
H1 H 0.486110 0.708136 0.688626 0.086 Uiso 1 1 calc R U . . .
C2 C 0.8577(18) 0.747(2) 0.6911(2) 0.075(3) Uani 1 1 d . . . . .
H2 H 0.880702 0.591918 0.683306 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8949(17) 0.702(2) 0.71416(19) 0.071(3) Uani 1 1 d . . . . .
H3 H 0.785687 0.567359 0.718497 0.085 Uiso 1 1 calc R U . . .
C4 C 0.8457(18) 0.910(2) 0.7288(2) 0.077(3) Uani 1 1 d . . . . .
H4 H 0.855312 0.858341 0.744228 0.092 Uiso 1 1 calc R U . . .
C5 C 0.590(2) 0.999(3) 0.7236(2) 0.081(3) Uani 1 1 d . . . . .
H5 H 0.473834 0.873311 0.728401 0.097 Uiso 1 1 calc R U . . .
C6 C 0.5409(18) 1.0513(19) 0.7007(2) 0.071(3) Uani 1 1 d . . . . .
H6 H 0.365176 1.086773 0.699059 0.086 Uiso 1 1 calc R U . . .
C7 C 0.5773(19) 0.920(3) 0.6630(2) 0.078(3) Uani 1 1 d . . . . .
H7A H 0.708157 1.034769 0.659714 0.093 Uiso 1 1 calc R U . . .
H7B H 0.422560 1.006776 0.661601 0.093 Uiso 1 1 calc R U . . .
C8 C 0.583(2) 0.714(3) 0.6458(2) 0.080(3) Uani 1 1 d . . . . .
H8A H 0.612730 0.787295 0.631485 0.095 Uiso 1 1 calc R U . . .
H8B H 0.722473 0.608662 0.648997 0.095 Uiso 1 1 calc R U . . .
C9 C 0.3617(19) 0.560(3) 0.64421(18) 0.071(3) Uani 1 1 d . . . . .
H9A H 0.218602 0.664691 0.642582 0.086 Uiso 1 1 calc R U . . .
H9B H 0.342790 0.468385 0.657756 0.086 Uiso 1 1 calc R U . . .
C10 C 0.372(2) 0.385(3) 0.6253(2) 0.077(3) Uani 1 1 d . . . . .
H10A H 0.401293 0.479564 0.612041 0.093 Uiso 1 1 calc R U . . .
H10B H 0.513286 0.279803 0.627421 0.093 Uiso 1 1 calc R U . . .
C11 C 0.158(2) 0.229(3) 0.6214(2) 0.077(3) Uani 1 1 d . . . . .
H11A H 0.013043 0.331806 0.619875 0.093 Uiso 1 1 calc R U . . .
H11B H 0.133272 0.124507 0.634076 0.093 Uiso 1 1 calc R U . . .
C12 C 0.184(2) 0.070(3) 0.6008(2) 0.081(3) Uani 1 1 d . . . . .
H12A H 0.207012 0.175329 0.588187 0.097 Uiso 1 1 calc R U . . .
H12B H 0.330008 -0.030569 0.602328 0.097 Uiso 1 1 calc R U . . .
C13 C -0.029(2) -0.091(2) 0.5967(2) 0.076(3) Uani 1 1 d . . . . .
H13A H -0.176517 0.007982 0.595374 0.092 Uiso 1 1 calc R U . . .
H13B H -0.051208 -0.199892 0.609184 0.092 Uiso 1 1 calc R U . . .
C14 C 0.002(2) -0.242(3) 0.5762(2) 0.088(4) Uani 1 1 d . . . . .
H14A H 0.023227 -0.132376 0.563746 0.105 Uiso 1 1 calc R U . . .
H14B H 0.150653 -0.338948 0.577505 0.105 Uiso 1 1 calc R U . . .
C15 C -0.211(3) -0.410(3) 0.5716(2) 0.087(3) Uani 1 1 d . . . . .
H15A H -0.232044 -0.519820 0.583960 0.104 Uiso 1 1 calc R U . . .
H15B H -0.359993 -0.312858 0.570281 0.104 Uiso 1 1 calc R U . . .
C16 C -0.181(3) -0.554(3) 0.5517(2) 0.093(4) Uani 1 1 d . . . . .
H16A H -0.035806 -0.656275 0.553141 0.112 Uiso 1 1 calc R U . . .
H16B H -0.155508 -0.445059 0.539314 0.112 Uiso 1 1 calc R U . . .
C17 C -0.404(3) -0.714(3) 0.5474(2) 0.089(4) Uani 1 1 d . . . . .
H17A H -0.547212 -0.611416 0.545160 0.107 Uiso 1 1 calc R U . . .
H17B H -0.434366 -0.816914 0.560099 0.107 Uiso 1 1 calc R U . . .
C18 C -0.366(4) -0.876(4) 0.5272(3) 0.119(6) Uani 1 1 d . . . . .
H18A H -0.335311 -0.773369 0.514434 0.143 Uiso 1 1 calc R U . . .
H18B H -0.223358 -0.979353 0.529391 0.143 Uiso 1 1 calc R U . . .
C19 C -0.584(4) -1.030(4) 0.5231(2) 0.116(6) Uani 1 1 d . . . . .
H19A H -0.617763 -1.128667 0.535974 0.139 Uiso 1 1 calc R U . . .
H19B H -0.725779 -0.926172 0.520402 0.139 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    'SIR2004 (Burla, et al., 2005)'
_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 1.400(11) . ?
F3 C3 1.413(12) . ?
F4 C4 1.396(11) . ?
F5 C5 1.430(16) . ?
F6 C6 1.413(11) . ?
O20 C19 1.397(19) . ?
O20 H20 0.98(3) . ?
C1 C7 1.495(18) . ?
C1 C6 1.533(16) . ?
C1 C2 1.535(15) . ?
C1 H1 1.0000 . ?
C2 C3 1.466(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.503(18) . ?
C3 H3 1.0000 . ?
C4 C5 1.537(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.478(19) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.570(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.503(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.491(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.562(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.507(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.538(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.536(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.48(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.55(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.56(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.50(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 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
C19 O20 H20 118(9) . . ?
C7 C1 C6 108.5(11) . . ?
C7 C1 C2 113.2(10) . . ?
C6 C1 C2 110.1(9) . . ?
C7 C1 H1 108.3 . . ?
C6 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
F2 C2 C3 111.2(8) . . ?
F2 C2 C1 108.7(10) . . ?
C3 C2 C1 113.2(9) . . ?
F2 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
F3 C3 C2 110.2(9) . . ?
F3 C3 C4 107.4(8) . . ?
C2 C3 C4 115.6(11) . . ?
F3 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
F4 C4 C3 111.4(9) . . ?
F4 C4 C5 108.0(10) . . ?
C3 C4 C5 106.9(10) . . ?
F4 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
C5 C4 H4 110.2 . . ?
F5 C5 C6 109.5(12) . . ?
F5 C5 C4 107.8(10) . . ?
C6 C5 C4 115.9(10) . . ?
F5 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
F6 C6 C5 109.7(9) . . ?
F6 C6 C1 109.4(9) . . ?
C5 C6 C1 112.6(11) . . ?
F6 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
C1 C6 H6 108.4 . . ?
C1 C7 C8 115.4(12) . . ?
C1 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C1 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 116.3(9) . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C10 112.6(9) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 117.9(9) . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10B 107.8 . . ?
C9 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
C10 C11 C12 113.0(10) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 113.9(10) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 112.2(11) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 113.5(10) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.4(11) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 111.5(12) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.4(13) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 110.9(15) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
O20 C19 C18 110.6(15) . . ?
O20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
O20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 47.7(13) . . . . ?
C6 C1 C2 F2 -73.9(12) . . . . ?
C7 C1 C2 C3 171.7(10) . . . . ?
C6 C1 C2 C3 50.1(13) . . . . ?
F2 C2 C3 F3 -54.6(12) . . . . ?
C1 C2 C3 F3 -177.3(9) . . . . ?
F2 C2 C3 C4 67.2(12) . . . . ?
C1 C2 C3 C4 -55.4(12) . . . . ?
F3 C3 C4 F4 58.9(13) . . . . ?
C2 C3 C4 F4 -64.5(12) . . . . ?
F3 C3 C4 C5 176.6(10) . . . . ?
C2 C3 C4 C5 53.2(12) . . . . ?
F4 C4 C5 F5 -55.6(13) . . . . ?
C3 C4 C5 F5 -175.5(10) . . . . ?
F4 C4 C5 C6 67.6(14) . . . . ?
C3 C4 C5 C6 -52.4(14) . . . . ?
F5 C5 C6 F6 53.2(12) . . . . ?
C4 C5 C6 F6 -69.1(13) . . . . ?
F5 C5 C6 C1 175.2(8) . . . . ?
C4 C5 C6 C1 52.9(13) . . . . ?
C7 C1 C6 F6 -50.9(11) . . . . ?
C2 C1 C6 F6 73.4(12) . . . . ?
C7 C1 C6 C5 -173.1(8) . . . . ?
C2 C1 C6 C5 -48.8(12) . . . . ?
C6 C1 C7 C8 -168.1(8) . . . . ?
C2 C1 C7 C8 69.5(12) . . . . ?
C1 C7 C8 C9 74.5(14) . . . . ?
C7 C8 C9 C10 173.1(11) . . . . ?
C8 C9 C10 C11 -177.4(12) . . . . ?
C9 C10 C11 C12 176.6(11) . . . . ?
C10 C11 C12 C13 179.4(11) . . . . ?
C11 C12 C13 C14 179.0(12) . . . . ?
C12 C13 C14 C15 179.5(12) . . . . ?
C13 C14 C15 C16 179.8(14) . . . . ?
C14 C15 C16 C17 -178.1(14) . . . . ?
C15 C16 C17 C18 -177.0(15) . . . . ?
C16 C17 C18 C19 -179.8(16) . . . . ?
C17 C18 C19 O20 -178.3(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O20 H20 O20 0.98(3) 2.38(14) 2.960(7) 118(11) 3_526 yes

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


