# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2202377'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_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         'C6 H9 F3'
_chemical_formula_sum            'C6 H9 F3'
_chemical_formula_weight         138.13
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7654(3)
_cell_length_b                   6.2994(4)
_cell_length_c                   10.5867(6)
_cell_angle_alpha                89.429(5)
_cell_angle_beta                 89.677(5)
_cell_angle_gamma                73.640(6)
_cell_volume                     304.92(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1705
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.5950
_cell_measurement_theta_min      4.2070
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.472
_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78702
_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    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3136
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.171
_diffrn_reflns_theta_min         4.176
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.968
_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   -113.00 -71.00   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    -85.00 -13.00   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    -85.00 -12.00   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   -128.00 -20.00   0.50   10.00    -- -110.00  72.00-135.00  216
 11  ω   -128.00 -20.00   0.50   10.00    -- -110.00  72.00  45.00  216
 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      -0.1545735000
_diffrn_orient_matrix_UB_12      -0.1336897000
_diffrn_orient_matrix_UB_13      -0.0818199000
_diffrn_orient_matrix_UB_21      -0.2890834000
_diffrn_orient_matrix_UB_22      0.1854827000
_diffrn_orient_matrix_UB_23      0.0120094000
_diffrn_orient_matrix_UB_31      0.0778343000
_diffrn_orient_matrix_UB_32      0.1126534000
_diffrn_orient_matrix_UB_33      -0.1197467000
_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                926
_reflns_number_total             1079
_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         0.332
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.092
_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)+(0.0791P)²+0.0534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1231
_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), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B)
;
_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
F1 F 0.6858(2) 0.04282(18) 0.14878(10) 0.0382(3) Uani 1 1 d . . . . .
F3 F 0.5131(2) 0.52351(17) 0.19160(10) 0.0386(4) Uani 1 1 d . . . . .
F5 F 0.6197(2) 0.21573(19) 0.40942(9) 0.0394(4) Uani 1 1 d . . . . .
C1 C 0.3801(4) 0.0747(3) 0.16233(16) 0.0305(4) Uani 1 1 d . . . . .
H1 H 0.323443 -0.037701 0.109923 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2186(4) 0.3033(3) 0.11312(16) 0.0315(4) Uani 1 1 d . . . . .
H2A H 0.302583 0.326382 0.030102 0.038 Uiso 1 1 calc R U . . .
H2B H 0.011284 0.308840 0.099474 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2298(4) 0.4917(3) 0.19928(16) 0.0319(4) Uani 1 1 d . . . . .
H3 H 0.083604 0.629683 0.168951 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1629(4) 0.4519(3) 0.33599(16) 0.0326(4) Uani 1 1 d . . . . .
H4A H -0.050119 0.473128 0.344870 0.039 Uiso 1 1 calc R U . . .
H4B H 0.214183 0.564538 0.388563 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3228(4) 0.2243(3) 0.38675(16) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.231058 0.201480 0.469064 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3118(4) 0.0378(3) 0.29915(15) 0.0316(4) Uani 1 1 d . . . . .
H6A H 0.452810 -0.100308 0.329610 0.038 Uiso 1 1 calc R U . . .
H6B H 0.114049 0.016386 0.304074 0.038 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
F1 C1 1.420(2) . ?
F3 C3 1.4216(19) . ?
F5 C5 1.422(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.517(2) . ?
C1 C6 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.517(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.514(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.516(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.516(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 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
F1 C1 H1 108.4 . . ?
F1 C1 C2 109.15(13) . . ?
F1 C1 C6 109.10(14) . . ?
C2 C1 H1 108.4 . . ?
C6 C1 H1 108.4 . . ?
C6 C1 C2 113.19(15) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 C1 114.63(14) . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
F3 C3 C2 108.88(14) . . ?
F3 C3 H3 108.5 . . ?
F3 C3 C4 108.90(14) . . ?
C2 C3 H3 108.5 . . ?
C4 C3 C2 113.33(14) . . ?
C4 C3 H3 108.5 . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C3 C4 C5 114.52(15) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
F5 C5 C4 109.03(13) . . ?
F5 C5 H5 108.3 . . ?
F5 C5 C6 109.23(15) . . ?
C4 C5 H5 108.3 . . ?
C4 C5 C6 113.53(15) . . ?
C6 C5 H5 108.3 . . ?
C1 C6 C5 114.60(14) . . ?
C1 C6 H6A 108.6 . . ?
C1 C6 H6B 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -74.63(18) . . . . ?
F1 C1 C6 C5 74.85(19) . . . . ?
F3 C3 C4 C5 -74.65(18) . . . . ?
F5 C5 C6 C1 -75.15(19) . . . . ?
C1 C2 C3 F3 74.33(17) . . . . ?
C1 C2 C3 C4 -47.0(2) . . . . ?
C2 C1 C6 C5 -46.9(2) . . . . ?
C2 C3 C4 C5 46.7(2) . . . . ?
C3 C4 C5 F5 75.42(18) . . . . ?
C3 C4 C5 C6 -46.6(2) . . . . ?
C4 C5 C6 C1 46.8(2) . . . . ?
C6 C1 C2 C3 47.1(2) . . . . ?

_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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 2202378'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
# start Validation Reply Form
_vrf_PLAT340_6                   
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01529 Ang.
RESPONSE: All crystals of this compound were apparently polycrystalline needes,
 leading to slightly poorer than ideal data-quality, including the
 bond-precision. 
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H11 F3'
_chemical_formula_sum            'C7 H11 F3'
_chemical_formula_weight         152.16
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           9
_space_group_name_H-M_alt        Cc
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   4.8224(10)
_cell_length_b                   12.4436(19)
_cell_length_c                   12.240(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.55(2)
_cell_angle_gamma                90
_cell_volume                     734.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.7530
_cell_measurement_theta_min      3.2760
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4594
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.933
_diffrn_reflns_theta_min         1.664
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  80.00   0.50   10.00    --  -10.00  45.00   0.00  360
  2  ω   -100.00  80.00   0.50   10.00    --  -10.00  45.00  90.00  360
  3  ω   -100.00  80.00   0.50   10.00    --  -10.00  45.00 180.00  360
;
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0915466500
_diffrn_orient_matrix_UB_12      0.0265659500
_diffrn_orient_matrix_UB_13      0.0368096000
_diffrn_orient_matrix_UB_21      -0.0800037000
_diffrn_orient_matrix_UB_22      0.0476445000
_diffrn_orient_matrix_UB_23      -0.0051518000
_diffrn_orient_matrix_UB_31      -0.0828643500
_diffrn_orient_matrix_UB_32      -0.0165245500
_diffrn_orient_matrix_UB_33      0.0444754000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.744
_reflns_number_gt                1177
_reflns_number_total             1567
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.745
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.154
_refine_ls_abs_structure_details 
;
 The calculated value of the Flack parameter, and its SU were found to be
 meaningless due to weak anomalous scattering by the crystal.  They were
 removed from the CIF.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1567
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1074
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_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          0.2769
_refine_ls_wR_factor_ref         0.2933
_refine_special_details          
;Refined as a 2-component twin. All crystals were slightly polycrystalline
 and diffracted weakly at high angles, data from the best of these is
 presented. Even this data shows signs that the twin law does not fully account
 for the polycrystallinity, resulting in the slightly elevated value of Rint.,Twin
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.702(11)
 0.298(11)
2. 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
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.6863(13) 0.5774(4) 0.4395(5) 0.0521(18) Uani 1 1 d . . . . .
F4 F 0.6784(15) 0.8037(5) 0.3738(6) 0.0542(18) Uani 1 1 d . . . . .
F6 F 0.6935(15) 0.7432(4) 0.6044(6) 0.0486(16) Uani 1 1 d . . . . .
C1 C 0.320(2) 0.6226(7) 0.5570(9) 0.043(2) Uani 1 1 d . . . . .
H1 H 0.112597 0.621303 0.559746 0.051 Uiso 1 1 calc R U . . .
C2 C 0.399(2) 0.5915(8) 0.4432(9) 0.040(2) Uani 1 1 d . . . . .
H2 H 0.307392 0.521628 0.424743 0.048 Uiso 1 1 calc R U . . .
C3 C 0.316(3) 0.6742(9) 0.3576(10) 0.051(3) Uani 1 1 d . . . . .
H3A H 0.112008 0.670895 0.346954 0.061 Uiso 1 1 calc R U . . .
H3B H 0.402062 0.654202 0.287395 0.061 Uiso 1 1 calc R U . . .
C4 C 0.397(3) 0.7905(8) 0.3851(10) 0.052(3) Uani 1 1 d . . . . .
H4 H 0.299352 0.839754 0.332866 0.062 Uiso 1 1 calc R U . . .
C5 C 0.311(2) 0.8192(6) 0.5010(11) 0.045(3) Uani 1 1 d . . . . .
H5A H 0.106080 0.823527 0.503503 0.055 Uiso 1 1 calc R U . . .
H5B H 0.385276 0.891222 0.519288 0.055 Uiso 1 1 calc R U . . .
C6 C 0.412(2) 0.7381(6) 0.5889(9) 0.037(2) Uani 1 1 d . . . . .
H6 H 0.321792 0.757029 0.659502 0.045 Uiso 1 1 calc R U . . .
C7 C 0.425(3) 0.5423(9) 0.6429(9) 0.055(3) Uani 1 1 d . . . . .
H7A H 0.346462 0.560234 0.714135 0.083 Uiso 1 1 calc R U . . .
H7B H 0.627914 0.545917 0.647470 0.083 Uiso 1 1 calc R U . . .
H7C H 0.368348 0.469494 0.621966 0.083 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 1.398(13) . ?
F4 C4 1.376(16) . ?
F6 C6 1.370(14) . ?
C1 H1 1.0000 . ?
C1 C2 1.498(16) . ?
C1 C6 1.553(12) . ?
C1 C7 1.533(15) . ?
C2 H2 1.0000 . ?
C2 C3 1.520(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.536(16) . ?
C4 H4 1.0000 . ?
C4 C5 1.52(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.551(15) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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 106.9 . . ?
C2 C1 C6 113.4(8) . . ?
C2 C1 C7 112.5(10) . . ?
C6 C1 H1 106.9 . . ?
C7 C1 H1 106.9 . . ?
C7 C1 C6 109.8(10) . . ?
F2 C2 C1 108.9(9) . . ?
F2 C2 H2 108.6 . . ?
F2 C2 C3 108.5(10) . . ?
C1 C2 H2 108.6 . . ?
C1 C2 C3 113.5(9) . . ?
C3 C2 H2 108.6 . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C2 C3 C4 114.9(10) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
F4 C4 C3 109.9(11) . . ?
F4 C4 H4 108.7 . . ?
F4 C4 C5 110.0(10) . . ?
C3 C4 H4 108.7 . . ?
C5 C4 C3 110.7(10) . . ?
C5 C4 H4 108.7 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C4 C5 C6 114.0(8) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
F6 C6 C1 111.0(8) . . ?
F6 C6 C5 111.8(8) . . ?
F6 C6 H6 108.0 . . ?
C1 C6 H6 108.0 . . ?
C5 C6 C1 109.9(9) . . ?
C5 C6 H6 108.0 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 C4 -72.5(14) . . . . ?
F4 C4 C5 C6 -69.8(10) . . . . ?
C1 C2 C3 C4 48.8(16) . . . . ?
C2 C1 C6 F6 -72.1(11) . . . . ?
C2 C1 C6 C5 52.1(14) . . . . ?
C2 C3 C4 F4 73.1(14) . . . . ?
C2 C3 C4 C5 -48.7(16) . . . . ?
C3 C4 C5 C6 51.9(15) . . . . ?
C4 C5 C6 F6 70.1(11) . . . . ?
C4 C5 C6 C1 -53.6(14) . . . . ?
C6 C1 C2 F2 70.7(11) . . . . ?
C6 C1 C2 C3 -50.3(14) . . . . ?
C7 C1 C2 F2 -54.6(11) . . . . ?
C7 C1 C2 C3 -175.6(10) . . . . ?
C7 C1 C6 F6 54.7(13) . . . . ?
C7 C1 C6 C5 178.9(9) . . . . ?

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.702(11)
2 0.298(11)

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

data_9
_database_code_depnum_ccdc_archive 'CCDC 2202380'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-07 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT082_9                   
;
PROBLEM: High R1 Value .................................. 0.18 Report
RESPONSE: All crystals of this compound were needles and showed signs of
 polycrystallinity or twinning that could not successfully be modelled, as well
 as extremely weak diffraction at high angles. This has resulted in elevated
 R-factors, among other issues, but still an unambiguous determination of
 structure.
;
_vrf_PLAT084_9                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.44 Report
RESPONSE: All crystals of this compound were needles and showed signs of
 polycrystallinity or twinning that could not successfully be modelled, as well
 as extremely weak diffraction at high angles. This has resulted in elevated
 R-factors, among other issues, but still an unambiguous determination of
 structure.
;
_vrf_PLAT097_9                   
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.36 eA-3
RESPONSE: All crystals of this compound were needles and showed signs of
 polycrystallinity or twinning that could not successfully be modelled, as well
 as extremely weak diffraction at high angles.  This has resulted in somewhat
 high residual electron density, among other issues, but still an unambiguous
 determination of structure.
;
_vrf_PLAT340_9                   
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01957 Ang.
RESPONSE: All crystals of this compound were needles and showed signs of
 polycrystallinity or twinning that could not successfully be modelled, as well
 as extremely weak diffraction at high angles.  This has resulted in poorer
 than ideal bond precision, among other issues, but still an unambiguous
 determination of structure.
;
# end Validation Reply Form

_audit_creation_date             2022-10-07
_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         'C8 H12 F3 N O'
_chemical_formula_sum            'C8 H12 F3 N O'
_chemical_formula_weight         195.19
_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'
N N 0.0311 0.0180 '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                   9.161(2)
_cell_length_b                   4.8349(8)
_cell_length_c                   9.983(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.30(3)
_cell_angle_gamma                90
_cell_volume                     426.50(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    917
_cell_measurement_temperature    125
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      7.64
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.659
_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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1421
_diffrn_reflns_av_unetI/netI     0.1422
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4826
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.686
_diffrn_reflns_theta_min         4.592
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                946
_reflns_number_total             1619
_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 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.358
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.212
_refine_ls_abs_structure_details 
;
 The calculated value of the Flack parameter, and its SU were found to be
 meaningless due to weak anomalous scattering by the crystal.  They were
 removed from the CIF.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.442
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2287
_refine_ls_R_factor_gt           0.1848
_refine_ls_restrained_S_all      1.442
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4092
_refine_ls_wR_factor_ref         0.4428
_refine_special_details          
;
 Crystals showed particularly weak diffraction with severe loss of data at
 higher angles, as well as signs of polycrystallinity or twinning that could
 not successfully be modelled, leading to elevated values of Rint, R1 and wR2.
 In addition the relative sizes of thermal ellipsoids for the three fluorine
 atoms suggests possible discrepancies in their occupancies such that they
 could refine to a total of only two fluorine atoms across the three sites.
 This can however be discounted on the basis of the chemical knowledge of the
 sample from other analytical techniques.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
 At 1.5 times of:
  All N(H) groups
2. Restrained distances
 N7-H7
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 N7(H7)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.866(2) 0.848(3) 0.3711(17) 0.125(5) Uani 1 1 d . . . . .
F4 F 0.6450(10) 0.8445(16) 0.1143(10) 0.063(3) Uani 1 1 d . . . . .
F6 F 0.5658(17) 0.856(3) 0.3691(16) 0.111(5) Uani 1 1 d . . . . .
O8 O 0.8049(12) 0.144(2) 0.6795(11) 0.058(3) Uani 1 1 d . . . . .
N7 N 0.7751(13) 0.566(2) 0.5842(11) 0.047(3) Uani 1 1 d D . . . .
H7 H 0.778357 0.765219 0.603498 0.071 Uiso 1 1 calc DR U . . .
C1 C 0.7354(15) 0.496(3) 0.4434(14) 0.052(4) Uani 1 1 d . . . . .
H1 H 0.733812 0.289464 0.443974 0.063 Uiso 1 1 calc R U . . .
C2 C 0.8497(15) 0.564(3) 0.3663(15) 0.048(3) Uani 1 1 d . . . . .
H2 H 0.948422 0.476759 0.414769 0.058 Uiso 1 1 calc R U . . .
C3 C 0.8087(17) 0.481(3) 0.2151(15) 0.055(4) Uani 1 1 d . . . . .
H3A H 0.878769 0.573177 0.168714 0.066 Uiso 1 1 calc R U . . .
H3B H 0.821502 0.279122 0.208256 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6488(14) 0.558(3) 0.1411(14) 0.043(3) Uani 1 1 d . . . . .
H4 H 0.622131 0.460238 0.049632 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5297(14) 0.489(3) 0.2142(15) 0.048(3) Uani 1 1 d . . . . .
H5A H 0.433949 0.581461 0.166054 0.058 Uiso 1 1 calc R U . . .
H5B H 0.511567 0.286544 0.208662 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5733(14) 0.575(3) 0.3640(15) 0.049(3) Uani 1 1 d . . . . .
H6 H 0.500527 0.492802 0.411931 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8082(15) 0.410(2) 0.6931(15) 0.047(3) Uani 1 1 d . . . . .
C9 C 0.8522(18) 0.529(2) 0.8338(13) 0.050(3) Uani 1 1 d . . . . .
H9A H 0.774418 0.486772 0.881796 0.059 Uiso 1 1 calc R U . . .
H9B H 0.862513 0.730005 0.827360 0.059 Uiso 1 1 calc R U . . .
H9C H 0.949086 0.449710 0.885710 0.059 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 1.38(2) . ?
F4 C4 1.409(15) . ?
F6 C6 1.36(2) . ?
O8 C8 1.293(14) . ?
N7 H7 0.9800 . ?
N7 C1 1.398(19) . ?
N7 C8 1.293(17) . ?
C1 H1 1.0000 . ?
C1 C2 1.49(2) . ?
C1 C6 1.535(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.51(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.50(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.502(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.50(2) . ?
C6 H6 1.0000 . ?
C8 C9 1.473(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 N7 H7 114.9 . . ?
C8 N7 H7 114.9 . . ?
C8 N7 C1 130.1(12) . . ?
N7 C1 H1 103.7 . . ?
N7 C1 C2 115.7(11) . . ?
N7 C1 C6 114.8(12) . . ?
C2 C1 H1 103.7 . . ?
C2 C1 C6 113.2(12) . . ?
C6 C1 H1 103.7 . . ?
F2 C2 C1 106.7(14) . . ?
F2 C2 H2 109.0 . . ?
F2 C2 C3 107.1(13) . . ?
C1 C2 H2 109.0 . . ?
C1 C2 C3 115.7(12) . . ?
C3 C2 H2 109.0 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.3(12) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
F4 C4 C3 107.9(11) . . ?
F4 C4 H4 107.7 . . ?
F4 C4 C5 109.1(11) . . ?
C3 C4 H4 107.7 . . ?
C5 C4 C3 116.4(12) . . ?
C5 C4 H4 107.7 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.7(11) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
F6 C6 C1 106.2(13) . . ?
F6 C6 C5 108.2(13) . . ?
F6 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C5 C6 C1 114.4(11) . . ?
C5 C6 H6 109.3 . . ?
O8 C8 C9 118.9(12) . . ?
N7 C8 O8 120.0(13) . . ?
N7 C8 C9 121.1(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
N7 H7 O8 0.98 1.97 2.938(15) 168.8 1_565 yes

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 -73.2(16) . . . . ?
F4 C4 C5 C6 -75.2(14) . . . . ?
N7 C1 C2 F2 -62.6(17) . . . . ?
N7 C1 C2 C3 178.4(13) . . . . ?
N7 C1 C6 F6 63.1(17) . . . . ?
N7 C1 C6 C5 -177.6(12) . . . . ?
C1 N7 C8 O8 -1(2) . . . . ?
C1 N7 C8 C9 177.9(14) . . . . ?
C1 C2 C3 C4 45.6(17) . . . . ?
C2 C1 C6 F6 -72.8(16) . . . . ?
C2 C1 C6 C5 46.4(17) . . . . ?
C2 C3 C4 F4 76.9(14) . . . . ?
C2 C3 C4 C5 -46.2(18) . . . . ?
C3 C4 C5 C6 47.3(18) . . . . ?
C4 C5 C6 F6 71.7(15) . . . . ?
C4 C5 C6 C1 -46.4(17) . . . . ?
C6 C1 C2 F2 72.9(16) . . . . ?
C6 C1 C2 C3 -46.1(17) . . . . ?
C8 N7 C1 C2 -110.6(18) . . . . ?
C8 N7 C1 C6 114.6(17) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/toluene'
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 2202382'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-07 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_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         'C11 H19 F2 N O2'
_chemical_formula_sum            'C11 H19 F2 N O2'
_chemical_formula_weight         235.27
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   21.5717(6)
_cell_length_b                   6.40500(10)
_cell_length_c                   18.7016(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.865(3)
_cell_angle_gamma                90
_cell_volume                     2472.81(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    30359
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.0000
_cell_measurement_theta_min      2.0300
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            79325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.393
_diffrn_reflns_theta_min         1.973
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00  82.00   0.50   10.00    --   -8.00  45.00 160.00  360
  2  ω    -98.00  82.00   0.50   10.00    --   -8.00  45.00 -20.00  360
  3  ω    -98.00  82.00   0.50   10.00    --   -8.00  45.00  52.00  360
  4  ω    -98.00  64.00   0.50   10.00    --   -8.00  45.00 232.00  324
  5  ω    -98.00  60.00   0.50   10.00    --   -8.00  45.00 305.00  316
  6  ω    -98.00  62.00   0.50   10.00    --   -8.00  45.00 124.00  320
  7  ω    -98.00  20.00   0.50   10.00    --   -8.00  45.00 268.00  236
  8  ω    -98.00  24.00   0.50   10.00    --   -8.00  45.00  88.00  244
  9  ω    -98.00  20.00   0.50   10.00    --   -8.00  45.00 196.00  236
 10  ω    -98.00  29.00   0.50   10.00    --   -8.00  45.00  16.00  254
;
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0082249000
_diffrn_orient_matrix_UB_12      -0.0087458000
_diffrn_orient_matrix_UB_13      -0.0339503000
_diffrn_orient_matrix_UB_21      -0.0333230000
_diffrn_orient_matrix_UB_22      0.0033592000
_diffrn_orient_matrix_UB_23      -0.0203393000
_diffrn_orient_matrix_UB_31      0.0016219000
_diffrn_orient_matrix_UB_32      0.1103285000
_diffrn_orient_matrix_UB_33      -0.0021069000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3996
_reflns_number_total             5643
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.504
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0911
_refine_ls_restrained_S_all      1.192
_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)+9.8900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2053
_refine_special_details          
;
 Crystals showed some degree of polycrystallinity that reduced diffraction
 intensity at high angles, the best  available data is presented. This could
 not be successfully modelled as twinning, and it has led to slightly elevated
 values of R1 and wR2. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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), C6(H6), C21(H21), C22(H22), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N27(H27)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
;
_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 0.38521(12) 0.6558(4) 0.44320(13) 0.0389(6) Uani 1 1 d . . . . .
F6 F 0.29004(13) 0.9332(4) 0.46295(13) 0.0409(6) Uani 1 1 d . . . . .
F22 F 0.33596(12) 0.3612(4) 0.71216(12) 0.0381(6) Uani 1 1 d . . . . .
F26 F 0.37152(12) 0.7779(4) 0.69429(13) 0.0397(6) Uani 1 1 d . . . . .
O8 O 0.21997(15) 0.7125(5) 0.21151(14) 0.0412(8) Uani 1 1 d . . . . .
O9 O 0.18697(14) 0.4481(5) 0.27352(14) 0.0344(7) Uani 1 1 d . . . . .
O28 O 0.22666(13) 0.4978(4) 0.46602(13) 0.0275(6) Uani 1 1 d . . . . .
O29 O 0.15987(13) 0.6501(5) 0.52574(14) 0.0312(6) Uani 1 1 d . . . . .
N7 N 0.26162(16) 0.6686(5) 0.33624(16) 0.0294(8) Uani 1 1 d . . . . .
H7 H 0.259101 0.596939 0.375451 0.035 Uiso 1 1 calc R U . . .
N27 N 0.26257(15) 0.5973(5) 0.58745(16) 0.0278(7) Uani 1 1 d . . . . .
H27 H 0.252112 0.650761 0.625733 0.033 Uiso 1 1 calc R U . . .
C1 C 0.30733(19) 0.8381(6) 0.34681(19) 0.0254(8) Uani 1 1 d . . . . .
H1 H 0.302184 0.898249 0.296070 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3763(2) 0.7644(6) 0.3747(2) 0.0298(9) Uani 1 1 d . . . . .
H2 H 0.385100 0.666726 0.337105 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4251(2) 0.9397(7) 0.3888(2) 0.0340(10) Uani 1 1 d . . . . .
H3A H 0.424829 1.004188 0.340650 0.041 Uiso 1 1 calc R U . . .
H3B H 0.468929 0.882735 0.412299 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4098(2) 1.1060(7) 0.4398(2) 0.0358(10) Uani 1 1 d . . . . .
H4A H 0.414739 1.045687 0.489859 0.043 Uiso 1 1 calc R U . . .
H4B H 0.440817 1.223157 0.445455 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3414(2) 1.1865(7) 0.4075(2) 0.0362(10) Uani 1 1 d . . . . .
H5A H 0.331821 1.288934 0.442519 0.043 Uiso 1 1 calc R U . . .
H5B H 0.338051 1.259759 0.359893 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2917(2) 1.0138(7) 0.3934(2) 0.0310(9) Uani 1 1 d . . . . .
H6 H 0.248146 1.072694 0.366742 0.037 Uiso 1 1 calc R U . . .
C8 C 0.22280(19) 0.6164(6) 0.2686(2) 0.0277(8) Uani 1 1 d . . . . .
C10 C 0.1346(2) 0.3796(7) 0.2078(2) 0.0362(10) Uani 1 1 d . . . . .
C11 C 0.0836(2) 0.5486(8) 0.1878(3) 0.0481(12) Uani 1 1 d . . . . .
H11A H 0.070887 0.587108 0.232342 0.072 Uiso 1 1 calc R U . . .
H11B H 0.045584 0.496962 0.149113 0.072 Uiso 1 1 calc R U . . .
H11C H 0.101115 0.671253 0.169118 0.072 Uiso 1 1 calc R U . . .
C12 C 0.1084(3) 0.1888(8) 0.2374(3) 0.0565(15) Uani 1 1 d . . . . .
H12A H 0.142688 0.083608 0.252928 0.085 Uiso 1 1 calc R U . . .
H12B H 0.071999 0.130751 0.198077 0.085 Uiso 1 1 calc R U . . .
H12C H 0.093617 0.228635 0.280340 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1611(3) 0.3214(9) 0.1437(3) 0.0557(14) Uani 1 1 d . . . . .
H13A H 0.173089 0.448535 0.121750 0.083 Uiso 1 1 calc R U . . .
H13B H 0.127878 0.245592 0.105579 0.083 Uiso 1 1 calc R U . . .
H13C H 0.199341 0.232579 0.162355 0.083 Uiso 1 1 calc R U . . .
C21 C 0.32843(18) 0.5326(7) 0.59640(19) 0.0270(8) Uani 1 1 d . . . . .
H21 H 0.330750 0.498606 0.545050 0.032 Uiso 1 1 calc R U . . .
C22 C 0.3461(2) 0.3306(7) 0.6417(2) 0.0309(9) Uani 1 1 d . . . . .
H22 H 0.317330 0.215279 0.614911 0.037 Uiso 1 1 calc R U . . .
C23 C 0.4154(2) 0.2691(7) 0.6537(2) 0.0378(10) Uani 1 1 d . . . . .
H23A H 0.421105 0.221428 0.605629 0.045 Uiso 1 1 calc R U . . .
H23B H 0.425861 0.150331 0.689043 0.045 Uiso 1 1 calc R U . . .
C24 C 0.4627(2) 0.4462(7) 0.6842(2) 0.0354(10) Uani 1 1 d . . . . .
H24A H 0.507140 0.400497 0.686966 0.042 Uiso 1 1 calc R U . . .
H24B H 0.461656 0.481462 0.735388 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4454(2) 0.6393(8) 0.6346(2) 0.0367(10) Uani 1 1 d . . . . .
H25A H 0.475029 0.754856 0.657374 0.044 Uiso 1 1 calc R U . . .
H25B H 0.451424 0.608410 0.585143 0.044 Uiso 1 1 calc R U . . .
C26 C 0.3763(2) 0.7069(7) 0.6243(2) 0.0330(9) Uani 1 1 d . . . . .
H26 H 0.365683 0.824888 0.587736 0.040 Uiso 1 1 calc R U . . .
C28 C 0.21716(18) 0.5771(6) 0.5216(2) 0.0245(8) Uani 1 1 d . . . . .
C30 C 0.10391(19) 0.6590(7) 0.4592(2) 0.0322(9) Uani 1 1 d . . . . .
C31 C 0.1173(2) 0.8091(9) 0.4022(3) 0.0497(13) Uani 1 1 d . . . . .
H31A H 0.133814 0.941266 0.426748 0.075 Uiso 1 1 calc R U . . .
H31B H 0.077079 0.834777 0.362261 0.075 Uiso 1 1 calc R U . . .
H31C H 0.149550 0.747654 0.380789 0.075 Uiso 1 1 calc R U . . .
C32 C 0.0518(2) 0.7462(9) 0.4900(3) 0.0446(12) Uani 1 1 d . . . . .
H32A H 0.047031 0.656261 0.530464 0.067 Uiso 1 1 calc R U . . .
H32B H 0.010636 0.751657 0.450159 0.067 Uiso 1 1 calc R U . . .
H32C H 0.063886 0.887274 0.509333 0.067 Uiso 1 1 calc R U . . .
C33 C 0.0859(2) 0.4429(8) 0.4271(3) 0.0443(12) Uani 1 1 d . . . . .
H33A H 0.119441 0.391844 0.405553 0.066 Uiso 1 1 calc R U . . .
H33B H 0.044286 0.448827 0.388098 0.066 Uiso 1 1 calc R U . . .
H33C H 0.082452 0.347999 0.466863 0.066 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 1.421(4) . ?
F6 C6 1.410(4) . ?
F22 C22 1.411(4) . ?
F26 C26 1.418(4) . ?
O8 C8 1.218(5) . ?
O9 C8 1.345(5) . ?
O9 C10 1.475(5) . ?
O28 C28 1.226(4) . ?
O29 C28 1.344(5) . ?
O29 C30 1.462(5) . ?
N7 H7 0.8800 . ?
N7 C1 1.441(5) . ?
N7 C8 1.342(5) . ?
N27 H27 0.8800 . ?
N27 C21 1.442(5) . ?
N27 C28 1.339(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.502(6) . ?
C1 C6 1.520(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.509(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.527(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.510(6) . ?
C6 H6 1.0000 . ?
C10 C11 1.511(7) . ?
C10 C12 1.517(7) . ?
C10 C13 1.516(6) . ?
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 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 H21 1.0000 . ?
C21 C22 1.532(6) . ?
C21 C26 1.508(6) . ?
C22 H22 1.0000 . ?
C22 C23 1.500(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.520(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.527(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.510(6) . ?
C26 H26 1.0000 . ?
C30 C31 1.524(6) . ?
C30 C32 1.511(6) . ?
C30 C33 1.514(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C8 O9 C10 119.9(3) . . ?
C28 O29 C30 120.7(3) . . ?
C1 N7 H7 118.9 . . ?
C8 N7 H7 118.9 . . ?
C8 N7 C1 122.1(3) . . ?
C21 N27 H27 119.6 . . ?
C28 N27 H27 119.6 . . ?
C28 N27 C21 120.8(3) . . ?
N7 C1 H1 106.1 . . ?
N7 C1 C2 112.3(3) . . ?
N7 C1 C6 112.3(3) . . ?
C2 C1 H1 106.1 . . ?
C2 C1 C6 113.3(3) . . ?
C6 C1 H1 106.1 . . ?
F2 C2 C1 109.2(3) . . ?
F2 C2 H2 108.9 . . ?
F2 C2 C3 107.5(3) . . ?
C1 C2 H2 108.9 . . ?
C1 C2 C3 113.4(4) . . ?
C3 C2 H2 108.9 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.3(3) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.5(3) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 112.4(4) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
F6 C6 C1 109.1(3) . . ?
F6 C6 C5 108.3(3) . . ?
F6 C6 H6 109.1 . . ?
C1 C6 H6 109.1 . . ?
C5 C6 C1 112.2(3) . . ?
C5 C6 H6 109.1 . . ?
O8 C8 O9 125.6(3) . . ?
O8 C8 N7 124.0(4) . . ?
N7 C8 O9 110.4(3) . . ?
O9 C10 C11 108.6(4) . . ?
O9 C10 C12 102.2(3) . . ?
O9 C10 C13 111.0(4) . . ?
C11 C10 C12 110.2(4) . . ?
C11 C10 C13 113.3(4) . . ?
C13 C10 C12 110.9(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N27 C21 H21 105.9 . . ?
N27 C21 C22 112.7(3) . . ?
N27 C21 C26 112.3(3) . . ?
C22 C21 H21 105.9 . . ?
C26 C21 H21 105.9 . . ?
C26 C21 C22 113.5(3) . . ?
F22 C22 C21 108.5(3) . . ?
F22 C22 H22 109.2 . . ?
F22 C22 C23 108.3(3) . . ?
C21 C22 H22 109.2 . . ?
C23 C22 C21 112.4(3) . . ?
C23 C22 H22 109.2 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C22 C23 C24 113.0(4) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C23 C24 C25 111.0(3) . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C26 C25 C24 111.6(3) . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
F26 C26 C21 109.3(3) . . ?
F26 C26 C25 107.9(3) . . ?
F26 C26 H26 109.0 . . ?
C21 C26 C25 112.5(4) . . ?
C21 C26 H26 109.0 . . ?
C25 C26 H26 109.0 . . ?
O28 C28 O29 125.1(3) . . ?
O28 C28 N27 124.2(4) . . ?
N27 C28 O29 110.7(3) . . ?
O29 C30 C31 110.1(4) . . ?
O29 C30 C32 102.2(3) . . ?
O29 C30 C33 110.8(3) . . ?
C32 C30 C31 110.3(4) . . ?
C32 C30 C33 110.8(4) . . ?
C33 C30 C31 112.2(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
N7 H7 O28 0.88 2.11 2.953(4) 160.3 . yes
N27 H27 O8 0.88 2.11 2.991(4) 175.4 4_576 yes

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 -68.0(4) . . . . ?
F22 C22 C23 C24 -69.3(4) . . . . ?
N7 C1 C2 F2 -58.1(4) . . . . ?
N7 C1 C2 C3 -178.0(3) . . . . ?
N7 C1 C6 F6 57.3(4) . . . . ?
N7 C1 C6 C5 177.3(3) . . . . ?
N27 C21 C22 F22 -57.6(4) . . . . ?
N27 C21 C22 C23 -177.4(3) . . . . ?
N27 C21 C26 F26 59.4(4) . . . . ?
N27 C21 C26 C25 179.4(3) . . . . ?
C1 N7 C8 O8 -4.2(6) . . . . ?
C1 N7 C8 O9 177.3(3) . . . . ?
C1 C2 C3 C4 52.8(4) . . . . ?
C2 C1 C6 F6 -71.3(4) . . . . ?
C2 C1 C6 C5 48.7(4) . . . . ?
C2 C3 C4 C5 -55.6(5) . . . . ?
C3 C4 C5 C6 56.1(4) . . . . ?
C4 C5 C6 F6 67.9(4) . . . . ?
C4 C5 C6 C1 -52.5(4) . . . . ?
C6 C1 C2 F2 70.5(4) . . . . ?
C6 C1 C2 C3 -49.4(4) . . . . ?
C8 O9 C10 C11 -64.2(5) . . . . ?
C8 O9 C10 C12 179.3(4) . . . . ?
C8 O9 C10 C13 61.0(5) . . . . ?
C8 N7 C1 C2 -115.0(4) . . . . ?
C8 N7 C1 C6 115.8(4) . . . . ?
C10 O9 C8 O8 -6.6(6) . . . . ?
C10 O9 C8 N7 171.8(3) . . . . ?
C21 N27 C28 O28 2.7(6) . . . . ?
C21 N27 C28 O29 -179.0(3) . . . . ?
C21 C22 C23 C24 50.6(5) . . . . ?
C22 C21 C26 F26 -69.8(4) . . . . ?
C22 C21 C26 C25 50.1(4) . . . . ?
C22 C23 C24 C25 -54.4(5) . . . . ?
C23 C24 C25 C26 55.3(5) . . . . ?
C24 C25 C26 F26 67.1(4) . . . . ?
C24 C25 C26 C21 -53.7(4) . . . . ?
C26 C21 C22 F22 71.4(4) . . . . ?
C26 C21 C22 C23 -48.4(4) . . . . ?
C28 O29 C30 C31 -63.5(5) . . . . ?
C28 O29 C30 C32 179.3(4) . . . . ?
C28 O29 C30 C33 61.2(5) . . . . ?
C28 N27 C21 C22 -106.7(4) . . . . ?
C28 N27 C21 C26 123.6(4) . . . . ?
C30 O29 C28 O28 -6.3(6) . . . . ?
C30 O29 C28 N27 175.4(3) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/methanol'
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2202381'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_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         'C11 H18 F3 N O2'
_chemical_formula_sum            'C11 H18 F3 N O2'
_chemical_formula_weight         253.26
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2763(4)
_cell_length_b                   9.5541(4)
_cell_length_c                   21.1552(10)
_cell_angle_alpha                95.696(4)
_cell_angle_beta                 96.546(5)
_cell_angle_gamma                98.362(5)
_cell_volume                     1238.20(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.7310
_cell_measurement_theta_min      4.9220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79490
_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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25453
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.117
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.972
_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   10.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50   10.00    --  -30.00 -72.00 -90.00  146
  3  ω   -113.00 -71.00   0.50   10.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50   10.00   0.00 -67.00   0.00    --   400
  5  ω    -85.00 -13.00   0.50   10.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50   10.00    --  -67.00 180.00   0.00   80
  7  ω    -85.00 -12.00   0.50   10.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50   10.00    --  -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   -128.00 -20.00   0.50   10.00    -- -110.00  72.00-135.00  216
 11  ω   -128.00 -20.00   0.50   10.00    -- -110.00  72.00  45.00  216
 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      0.1551216000
_diffrn_orient_matrix_UB_12      0.0984653000
_diffrn_orient_matrix_UB_13      0.0532045000
_diffrn_orient_matrix_UB_21      0.0474240000
_diffrn_orient_matrix_UB_22      0.1090514000
_diffrn_orient_matrix_UB_23      -0.0475748000
_diffrn_orient_matrix_UB_31      -0.1905372000
_diffrn_orient_matrix_UB_32      0.0731322000
_diffrn_orient_matrix_UB_33      0.0188270000
_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                4680
_reflns_number_total             8795
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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    'SIR2011  (Burla et al.,  2007)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         8795
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      0.852
_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)+(0.0774P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4988(11)
 0.5012(11)
2. 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
3. Restrained distances
 N7-H7 = N27-H27
 0.98 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6), C21(H21), C22(H22), C24(H24), C26(H26)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C23(H23A,H23B), C25(H25A,H25B)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.5908(3) 0.59908(18) 0.32910(9) 0.0485(5) Uani 1 1 d . . . . .
F4 F 0.5054(3) 0.65221(19) 0.46000(9) 0.0524(5) Uani 1 1 d . . . . .
F6 F 0.1905(3) 0.69004(18) 0.35568(9) 0.0485(5) Uani 1 1 d . . . . .
F22 F 0.3018(3) 0.21450(19) 0.38774(9) 0.0476(5) Uani 1 1 d . . . . .
F24 F -0.1080(3) 0.1571(2) 0.43770(9) 0.0555(5) Uani 1 1 d . . . . .
F26 F -0.0475(3) 0.06917(18) 0.30403(10) 0.0512(5) Uani 1 1 d . . . . .
O8 O 0.3849(4) 0.9981(2) 0.22151(11) 0.0473(6) Uani 1 1 d . . . . .
O9 O 0.2281(4) 0.7974(2) 0.15498(10) 0.0463(6) Uani 1 1 d . . . . .
O28 O 0.2638(3) 0.4798(2) 0.21110(10) 0.0392(5) Uani 1 1 d . . . . .
O29 O 0.4790(3) 0.3173(2) 0.18433(10) 0.0430(6) Uani 1 1 d . . . . .
N7 N 0.3880(5) 0.7768(3) 0.25146(13) 0.0412(7) Uani 1 1 d D . . . .
H7 H 0.332(5) 0.681(3) 0.2392(15) 0.058(11) Uiso 1 1 d D . . . .
N27 N 0.2556(4) 0.2744(3) 0.25701(13) 0.0378(6) Uani 1 1 d D . . . .
H27 H 0.307(5) 0.189(3) 0.2553(14) 0.041(9) Uiso 1 1 d D . . . .
C1 C 0.4851(5) 0.8264(3) 0.31648(15) 0.0366(7) Uani 1 1 d . . . . .
H1 H 0.552859 0.927775 0.316389 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6683(5) 0.7477(3) 0.33811(15) 0.0386(8) Uani 1 1 d . . . . .
H2 H 0.786851 0.767790 0.310880 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7622(5) 0.7914(3) 0.40770(15) 0.0415(8) Uani 1 1 d . . . . .
H3A H 0.861029 0.724581 0.420740 0.050 Uiso 1 1 calc R U . . .
H3B H 0.849965 0.887489 0.411567 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5944(5) 0.7941(3) 0.45329(16) 0.0416(8) Uani 1 1 d . . . . .
H4 H 0.666939 0.842172 0.496067 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4118(5) 0.8715(3) 0.43088(15) 0.0419(8) Uani 1 1 d . . . . .
H5A H 0.295153 0.854012 0.458279 0.050 Uiso 1 1 calc R U . . .
H5B H 0.466610 0.975078 0.436937 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3158(5) 0.8289(3) 0.36208(15) 0.0395(8) Uani 1 1 d . . . . .
H6 H 0.217759 0.897831 0.349300 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3355(5) 0.8684(3) 0.21025(15) 0.0383(8) Uani 1 1 d . . . . .
C10 C 0.1551(6) 0.8731(4) 0.10179(16) 0.0476(9) Uani 1 1 d . . . . .
C11 C -0.0022(8) 0.9677(5) 0.1219(2) 0.0979(18) Uani 1 1 d . . . . .
H11A H -0.115891 0.912668 0.141533 0.147 Uiso 1 1 calc R U . . .
H11B H -0.068242 1.005535 0.084304 0.147 Uiso 1 1 calc R U . . .
H11C H 0.074891 1.046820 0.153017 0.147 Uiso 1 1 calc R U . . .
C12 C 0.0414(7) 0.7533(4) 0.05123(17) 0.0654(11) Uani 1 1 d . . . . .
H12A H 0.141188 0.686041 0.042471 0.098 Uiso 1 1 calc R U . . .
H12B H -0.003752 0.793006 0.011774 0.098 Uiso 1 1 calc R U . . .
H12C H -0.086719 0.703732 0.066822 0.098 Uiso 1 1 calc R U . . .
C13 C 0.3503(7) 0.9540(5) 0.0773(2) 0.0951(17) Uani 1 1 d . . . . .
H13A H 0.420897 1.032293 0.109777 0.143 Uiso 1 1 calc R U . . .
H13B H 0.302103 0.992641 0.037824 0.143 Uiso 1 1 calc R U . . .
H13C H 0.453633 0.889196 0.068451 0.143 Uiso 1 1 calc R U . . .
C21 C 0.1119(5) 0.3113(3) 0.30244(15) 0.0353(7) Uani 1 1 d . . . . .
H21 H 0.068634 0.403630 0.291628 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2236(5) 0.3401(3) 0.37118(15) 0.0386(8) Uani 1 1 d . . . . .
H22 H 0.349843 0.418397 0.373862 0.046 Uiso 1 1 calc R U . . .
C23 C 0.0753(5) 0.3822(3) 0.41854(15) 0.0429(8) Uani 1 1 d . . . . .
H23A H 0.048377 0.480176 0.413299 0.051 Uiso 1 1 calc R U . . .
H23B H 0.150305 0.383503 0.462431 0.051 Uiso 1 1 calc R U . . .
C24 C -0.1407(5) 0.2849(3) 0.41177(17) 0.0434(8) Uani 1 1 d . . . . .
H24 H -0.241069 0.332845 0.436849 0.052 Uiso 1 1 calc R U . . .
C25 C -0.2458(5) 0.2481(3) 0.34288(16) 0.0438(8) Uani 1 1 d . . . . .
H25A H -0.367604 0.168689 0.341086 0.053 Uiso 1 1 calc R U . . .
H25B H -0.308124 0.331375 0.329205 0.053 Uiso 1 1 calc R U . . .
C26 C -0.0976(5) 0.2061(3) 0.29568(16) 0.0389(8) Uani 1 1 d . . . . .
H26 H -0.174693 0.203071 0.251383 0.047 Uiso 1 1 calc R U . . .
C28 C 0.3284(5) 0.3672(3) 0.21696(14) 0.0336(7) Uani 1 1 d . . . . .
C30 C 0.5941(5) 0.4057(3) 0.14117(16) 0.0438(8) Uani 1 1 d . . . . .
C31 C 0.4341(6) 0.4383(5) 0.08762(17) 0.0716(12) Uani 1 1 d . . . . .
H31A H 0.341209 0.349807 0.067816 0.107 Uiso 1 1 calc R U . . .
H31B H 0.513472 0.481687 0.055339 0.107 Uiso 1 1 calc R U . . .
H31C H 0.343956 0.504432 0.105028 0.107 Uiso 1 1 calc R U . . .
C32 C 0.7483(6) 0.3117(4) 0.11602(18) 0.0598(11) Uani 1 1 d . . . . .
H32A H 0.842493 0.287039 0.152084 0.090 Uiso 1 1 calc R U . . .
H32B H 0.837526 0.362919 0.087924 0.090 Uiso 1 1 calc R U . . .
H32C H 0.664486 0.224428 0.091815 0.090 Uiso 1 1 calc R U . . .
C33 C 0.7229(6) 0.5395(4) 0.17984(18) 0.0549(10) Uani 1 1 d . . . . .
H33A H 0.623315 0.603913 0.192597 0.082 Uiso 1 1 calc R U . . .
H33B H 0.824207 0.586912 0.153745 0.082 Uiso 1 1 calc R U . . .
H33C H 0.804569 0.514017 0.218195 0.082 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 1.419(3) . ?
F4 C4 1.416(3) . ?
F6 C6 1.426(3) . ?
F22 C22 1.421(3) . ?
F24 C24 1.419(3) . ?
F26 C26 1.413(3) . ?
O8 C8 1.225(4) . ?
O9 C8 1.346(4) . ?
O9 C10 1.463(4) . ?
O28 C28 1.216(3) . ?
O29 C28 1.346(3) . ?
O29 C30 1.482(3) . ?
N7 H7 0.93(2) . ?
N7 C1 1.443(4) . ?
N7 C8 1.343(4) . ?
N27 H27 0.92(2) . ?
N27 C21 1.444(4) . ?
N27 C28 1.354(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.516(4) . ?
C1 C6 1.516(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.516(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.508(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.509(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.503(4) . ?
C6 H6 1.0000 . ?
C10 C11 1.500(5) . ?
C10 C12 1.519(5) . ?
C10 C13 1.522(5) . ?
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 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 H21 1.0000 . ?
C21 C22 1.521(4) . ?
C21 C26 1.518(4) . ?
C22 H22 1.0000 . ?
C22 C23 1.507(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.511(4) . ?
C24 H24 1.0000 . ?
C24 C25 1.515(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.505(4) . ?
C26 H26 1.0000 . ?
C30 C31 1.513(5) . ?
C30 C32 1.517(4) . ?
C30 C33 1.516(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C8 O9 C10 121.2(2) . . ?
C28 O29 C30 120.5(2) . . ?
C1 N7 H7 121(2) . . ?
C8 N7 H7 117(2) . . ?
C8 N7 C1 121.3(3) . . ?
C21 N27 H27 121.7(19) . . ?
C28 N27 H27 117.0(19) . . ?
C28 N27 C21 121.2(3) . . ?
N7 C1 H1 106.2 . . ?
N7 C1 C2 112.3(3) . . ?
N7 C1 C6 111.8(3) . . ?
C2 C1 H1 106.2 . . ?
C2 C1 C6 113.6(3) . . ?
C6 C1 H1 106.2 . . ?
F2 C2 C1 109.1(2) . . ?
F2 C2 H2 108.5 . . ?
F2 C2 C3 109.0(2) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 113.0(3) . . ?
C3 C2 H2 108.5 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.3(3) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
F4 C4 C3 108.9(2) . . ?
F4 C4 H4 108.8 . . ?
F4 C4 C5 108.6(3) . . ?
C3 C4 H4 108.8 . . ?
C3 C4 C5 112.9(3) . . ?
C5 C4 H4 108.8 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C4 114.5(3) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
F6 C6 C1 108.0(2) . . ?
F6 C6 C5 109.4(3) . . ?
F6 C6 H6 108.7 . . ?
C1 C6 H6 108.7 . . ?
C5 C6 C1 113.3(3) . . ?
C5 C6 H6 108.7 . . ?
O8 C8 O9 125.4(3) . . ?
O8 C8 N7 124.0(3) . . ?
N7 C8 O9 110.5(3) . . ?
O9 C10 C11 110.2(3) . . ?
O9 C10 C12 103.1(3) . . ?
O9 C10 C13 109.9(3) . . ?
C11 C10 C12 110.5(3) . . ?
C11 C10 C13 112.8(4) . . ?
C12 C10 C13 110.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N27 C21 H21 105.9 . . ?
N27 C21 C22 113.0(2) . . ?
N27 C21 C26 113.1(3) . . ?
C22 C21 H21 105.9 . . ?
C26 C21 H21 105.9 . . ?
C26 C21 C22 112.2(3) . . ?
F22 C22 C21 108.3(2) . . ?
F22 C22 H22 108.8 . . ?
F22 C22 C23 108.9(2) . . ?
C21 C22 H22 108.8 . . ?
C23 C22 C21 113.1(3) . . ?
C23 C22 H22 108.8 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C22 C23 C24 114.2(3) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
F24 C24 C23 108.7(3) . . ?
F24 C24 H24 108.7 . . ?
F24 C24 C25 108.8(3) . . ?
C23 C24 H24 108.7 . . ?
C23 C24 C25 113.1(3) . . ?
C25 C24 H24 108.7 . . ?
C24 C25 H25A 108.4 . . ?
C24 C25 H25B 108.4 . . ?
H25A C25 H25B 107.5 . . ?
C26 C25 C24 115.4(3) . . ?
C26 C25 H25A 108.4 . . ?
C26 C25 H25B 108.4 . . ?
F26 C26 C21 109.1(2) . . ?
F26 C26 C25 110.1(3) . . ?
F26 C26 H26 108.5 . . ?
C21 C26 H26 108.5 . . ?
C25 C26 C21 112.1(3) . . ?
C25 C26 H26 108.5 . . ?
O28 C28 O29 125.0(3) . . ?
O28 C28 N27 124.1(3) . . ?
O29 C28 N27 110.9(2) . . ?
O29 C30 C31 110.2(3) . . ?
O29 C30 C32 103.1(2) . . ?
O29 C30 C33 109.4(3) . . ?
C31 C30 C32 111.6(3) . . ?
C31 C30 C33 112.4(3) . . ?
C33 C30 C32 109.7(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
N7 H7 O28 0.93(2) 1.92(2) 2.848(3) 171(3) . yes
N27 H27 O8 0.92(2) 2.04(2) 2.926(3) 162(3) 1_545 yes

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 -73.3(3) . . . . ?
F4 C4 C5 C6 -73.0(3) . . . . ?
F22 C22 C23 C24 -71.4(3) . . . . ?
F24 C24 C25 C26 -75.1(3) . . . . ?
N7 C1 C2 F2 -54.7(3) . . . . ?
N7 C1 C2 C3 -176.1(3) . . . . ?
N7 C1 C6 F6 55.2(3) . . . . ?
N7 C1 C6 C5 176.5(3) . . . . ?
N27 C21 C22 F22 -60.6(3) . . . . ?
N27 C21 C22 C23 178.6(3) . . . . ?
N27 C21 C26 F26 58.6(3) . . . . ?
N27 C21 C26 C25 -179.2(3) . . . . ?
C1 N7 C8 O8 8.0(5) . . . . ?
C1 N7 C8 O9 -173.8(3) . . . . ?
C1 C2 C3 C4 48.2(4) . . . . ?
C2 C1 C6 F6 -73.2(3) . . . . ?
C2 C1 C6 C5 48.1(4) . . . . ?
C2 C3 C4 F4 72.8(3) . . . . ?
C2 C3 C4 C5 -47.9(4) . . . . ?
C3 C4 C5 C6 48.0(4) . . . . ?
C4 C5 C6 F6 72.3(3) . . . . ?
C4 C5 C6 C1 -48.2(4) . . . . ?
C6 C1 C2 F2 73.5(3) . . . . ?
C6 C1 C2 C3 -48.0(4) . . . . ?
C8 O9 C10 C11 -61.3(4) . . . . ?
C8 O9 C10 C12 -179.1(3) . . . . ?
C8 O9 C10 C13 63.7(4) . . . . ?
C8 N7 C1 C2 -137.7(3) . . . . ?
C8 N7 C1 C6 93.3(3) . . . . ?
C10 O9 C8 O8 -1.0(5) . . . . ?
C10 O9 C8 N7 -179.2(3) . . . . ?
C21 N27 C28 O28 -7.9(5) . . . . ?
C21 N27 C28 O29 172.8(3) . . . . ?
C21 C22 C23 C24 49.1(4) . . . . ?
C22 C21 C26 F26 -70.7(3) . . . . ?
C22 C21 C26 C25 51.5(3) . . . . ?
C22 C23 C24 F24 75.7(3) . . . . ?
C22 C23 C24 C25 -45.2(4) . . . . ?
C23 C24 C25 C26 45.8(4) . . . . ?
C24 C25 C26 F26 72.5(3) . . . . ?
C24 C25 C26 C21 -49.2(4) . . . . ?
C26 C21 C22 F22 68.7(3) . . . . ?
C26 C21 C22 C23 -52.1(3) . . . . ?
C28 O29 C30 C31 -61.9(4) . . . . ?
C28 O29 C30 C32 178.9(3) . . . . ?
C28 O29 C30 C33 62.2(4) . . . . ?
C28 N27 C21 C22 -106.9(3) . . . . ?
C28 N27 C21 C26 124.2(3) . . . . ?
C30 O29 C28 O28 5.3(4) . . . . ?
C30 O29 C28 N27 -175.4(3) . . . . ?

_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4988(11) 12402 712 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5012(11) 12339 712 nmt 0.9371 0.0033 -0.0771 0.0397 1.0060 0.0790 0.7936
-0.3044 0.9704

_twin_special_details            
;
Component 2 rotated by 16.8755° 
 around [-0.34 -0.91 0.24] (reciprocal) or [-0.71 -0.70 -0.02] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/dichloromethane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 2202379'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-17
_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         'C7 H11 F3 O'
_chemical_formula_sum            'C7 H11 F3 O'
_chemical_formula_weight         168.16
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.7188(9)
_cell_length_b                   7.5388(5)
_cell_length_c                   8.2612(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.350(8)
_cell_angle_gamma                90
_cell_volume                     770.72(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5294
_cell_measurement_temperature    173
_cell_measurement_theta_max      36.4860
_cell_measurement_theta_min      3.1650
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.38a (Rigaku Oxford Diffraction, 2021)
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    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16213
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.742
_diffrn_reflns_theta_min         3.164
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50    2.00    --  -30.00  54.00   0.00  360
  2  ω   -120.00  60.00   0.50    2.00    --  -30.00  54.00  90.00  360
  3  ω   -120.00  60.00   0.50    2.00    --  -30.00  54.00 180.00  360
  4  ω   -120.00  60.00   0.50    2.00    --  -30.00  54.00 -90.00  360
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0498358000
_diffrn_orient_matrix_UB_12      -0.0465778000
_diffrn_orient_matrix_UB_13      -0.0180419000
_diffrn_orient_matrix_UB_21      -0.0278515000
_diffrn_orient_matrix_UB_22      0.0801742000
_diffrn_orient_matrix_UB_23      0.0070522000
_diffrn_orient_matrix_UB_31      -0.0054220000
_diffrn_orient_matrix_UB_32      0.0163180000
_diffrn_orient_matrix_UB_33      -0.0859929000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2434
_reflns_number_total             3673
_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 1.171.42.38a (Rigaku OD, 2021)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.42.38a (Rigaku OD, 2021)'
_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         0.441
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.058
_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)+(0.0744P)²+0.0375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1421
_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), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.14838(6) 0.84959(9) 0.32893(10) 0.03966(19) Uani 1 1 d . . . . .
F4 F 0.08899(6) 0.24502(9) 0.41482(9) 0.03647(18) Uani 1 1 d . . . . .
F6 F 0.38066(6) 0.41725(11) 0.19018(10) 0.0429(2) Uani 1 1 d . . . . .
O7 O 0.33574(6) 0.65355(12) 0.43012(9) 0.03295(19) Uani 1 1 d . . . . .
C1 C 0.27277(8) 0.64216(13) 0.26707(12) 0.02529(18) Uani 1 1 d . . . . .
H1 H 0.298411 0.730614 0.194568 0.030 Uiso 1 1 calc R U . . .
C2 C 0.15687(8) 0.67866(13) 0.26933(13) 0.02572(19) Uani 1 1 d . . . . .
H2 H 0.111819 0.670448 0.153105 0.031 Uiso 1 1 calc R U . . .
C3 C 0.11441(8) 0.54944(13) 0.37662(12) 0.02636(19) Uani 1 1 d . . . . .
H3A H 0.038125 0.577113 0.375286 0.032 Uiso 1 1 calc R U . . .
H3B H 0.157148 0.557329 0.492863 0.032 Uiso 1 1 calc R U . . .
C4 C 0.12277(8) 0.36609(13) 0.30978(12) 0.02577(19) Uani 1 1 d . . . . .
H4 H 0.074213 0.357018 0.196117 0.031 Uiso 1 1 calc R U . . .
C5 C 0.23606(8) 0.32066(14) 0.30024(14) 0.0295(2) Uani 1 1 d . . . . .
H5A H 0.237527 0.201951 0.249573 0.035 Uiso 1 1 calc R U . . .
H5B H 0.283693 0.318062 0.413422 0.035 Uiso 1 1 calc R U . . .
C6 C 0.27549(8) 0.45814(14) 0.19639(12) 0.0276(2) Uani 1 1 d . . . . .
H6 H 0.228782 0.455365 0.081044 0.033 Uiso 1 1 calc R U . . .
C8 C 0.43732(10) 0.7336(2) 0.44156(18) 0.0455(3) Uani 1 1 d . . . . .
H8A H 0.478476 0.664649 0.376738 0.068 Uiso 1 1 calc R U . . .
H8B H 0.476990 0.737109 0.558278 0.068 Uiso 1 1 calc R U . . .
H8C H 0.427129 0.854701 0.397612 0.068 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 1.3925(11) . ?
F4 C4 1.3939(11) . ?
F6 C6 1.3852(11) . ?
O7 C1 1.4018(12) . ?
O7 C8 1.4092(14) . ?
C1 H1 1.0000 . ?
C1 C2 1.5039(13) . ?
C1 C6 1.5086(14) . ?
C2 H2 1.0000 . ?
C2 C3 1.4991(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5014(14) . ?
C4 H4 1.0000 . ?
C4 C5 1.5006(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5034(14) . ?
C6 H6 1.0000 . ?
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
C1 O7 C8 113.72(9) . . ?
O7 C1 H1 110.0 . . ?
O7 C1 C2 108.73(8) . . ?
O7 C1 C6 111.66(8) . . ?
C2 C1 H1 110.0 . . ?
C2 C1 C6 106.45(8) . . ?
C6 C1 H1 110.0 . . ?
F2 C2 C1 109.27(8) . . ?
F2 C2 H2 108.8 . . ?
F2 C2 C3 108.93(8) . . ?
C1 C2 H2 108.8 . . ?
C3 C2 C1 112.11(8) . . ?
C3 C2 H2 108.8 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C2 C3 C4 108.36(8) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
F4 C4 C3 108.40(8) . . ?
F4 C4 H4 109.1 . . ?
F4 C4 C5 108.72(8) . . ?
C3 C4 H4 109.1 . . ?
C5 C4 C3 112.32(8) . . ?
C5 C4 H4 109.1 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C4 C5 C6 108.87(8) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
F6 C6 C1 109.12(9) . . ?
F6 C6 C5 108.66(9) . . ?
F6 C6 H6 109.0 . . ?
C1 C6 H6 109.0 . . ?
C5 C6 C1 111.88(8) . . ?
C5 C6 H6 109.0 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 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
F2 C2 C3 C4 179.31(8) . . . . ?
F4 C4 C5 C6 -176.21(8) . . . . ?
O7 C1 C2 F2 61.35(10) . . . . ?
O7 C1 C2 C3 -59.50(11) . . . . ?
O7 C1 C6 F6 -61.86(10) . . . . ?
O7 C1 C6 C5 58.41(11) . . . . ?
C1 C2 C3 C4 -59.63(11) . . . . ?
C2 C1 C6 F6 179.62(8) . . . . ?
C2 C1 C6 C5 -60.11(11) . . . . ?
C2 C3 C4 F4 176.72(8) . . . . ?
C2 C3 C4 C5 56.56(11) . . . . ?
C3 C4 C5 C6 -56.25(11) . . . . ?
C4 C5 C6 F6 179.05(8) . . . . ?
C4 C5 C6 C1 58.50(11) . . . . ?
C6 C1 C2 F2 -178.22(8) . . . . ?
C6 C1 C2 C3 60.93(10) . . . . ?
C8 O7 C1 C2 -141.41(10) . . . . ?
C8 O7 C1 C6 101.43(11) . . . . ?

_exptl_crystal_recrystallization_method 'Freezing the liquid sample'
