# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_a31224a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 F3 N O'
_chemical_formula_weight         369.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.398(4)
_cell_length_b                   10.644(4)
_cell_length_c                   18.906(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.921(6)
_cell_angle_gamma                90
_cell_volume                     1857.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    851
_cell_measurement_theta_min      2.207
_cell_measurement_theta_max      25.362

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.294
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8845
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.194
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3993
_reflns_number_gt                2193
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0921P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3993
_refine_ls_number_parameters     274
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
N1 N 0.49598(17) 0.43058(17) 0.15467(9) 0.0537(5) Uani 1 1 d . . . . .
O1 O 0.32366(17) 0.37626(16) 0.06093(9) 0.0723(5) Uani 1 1 d . . . . .
F1 F -0.054(3) 0.813(3) 0.2380(9) 0.216(11) Uani 0.349(17) 1 d . U P A 1
F2 F -0.1799(12) 0.7576(12) 0.1511(11) 0.126(6) Uani 0.349(17) 1 d . U P A 1
F3 F -0.044(2) 0.8909(13) 0.1389(17) 0.161(7) Uani 0.349(17) 1 d . U P A 1
F1' F -0.1053(8) 0.7609(6) 0.2329(6) 0.132(3) Uani 0.651(17) 1 d D U P A 2
F2' F 0.0009(7) 0.9053(5) 0.1943(8) 0.135(3) Uani 0.651(17) 1 d D U P A 2
F3' F -0.1595(13) 0.8016(16) 0.1218(6) 0.207(6) Uani 0.651(17) 1 d D U P A 2
C1 C 0.3612(2) 0.43634(19) 0.11520(13) 0.0549(5) Uani 1 1 d . . . . .
C2 C 0.2578(2) 0.5274(2) 0.13751(11) 0.0524(5) Uani 1 1 d . . . . .
C3 C 0.2965(2) 0.6496(2) 0.15145(12) 0.0597(6) Uani 1 1 d . . . . .
H3 H 0.3919 0.6744 0.1530 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1956(2) 0.7361(2) 0.16315(13) 0.0636(6) Uani 1 1 d . . . . .
H4 H 0.2221 0.8197 0.1716 0.076 Uiso 1 1 calc R U . . .
C5 C 0.0580(2) 0.7000(2) 0.16235(13) 0.0660(6) Uani 1 1 d . . . . .
C6 C 0.0189(3) 0.5787(3) 0.14916(17) 0.0845(9) Uani 1 1 d . . . . .
H6 H -0.0762 0.5541 0.1488 0.101 Uiso 1 1 calc R U . . .
C7 C 0.1184(3) 0.4919(2) 0.13628(16) 0.0761(8) Uani 1 1 d . . . . .
H7 H 0.0906 0.4089 0.1267 0.091 Uiso 1 1 calc R U . . .
C8 C -0.0512(4) 0.7925(3) 0.1753(2) 0.0943(10) Uani 1 1 d D . . . .
C9 C 0.5304(2) 0.46563(19) 0.22846(11) 0.0500(5) Uani 1 1 d . . . . .
C10 C 0.6418(2) 0.5477(2) 0.25154(12) 0.0562(5) Uani 1 1 d . . . . .
H10 H 0.6922 0.5829 0.2186 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6787(2) 0.5776(2) 0.32231(12) 0.0587(6) Uani 1 1 d . . . . .
H11 H 0.7554 0.6327 0.3371 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6066(2) 0.5294(2) 0.37280(12) 0.0567(6) Uani 1 1 d . . . . .
C13 C 0.4948(2) 0.4481(2) 0.34835(12) 0.0593(6) Uani 1 1 d . . . . .
H13 H 0.4433 0.4139 0.3811 0.071 Uiso 1 1 calc R U . . .
C14 C 0.4571(2) 0.4161(2) 0.27759(12) 0.0555(5) Uani 1 1 d . . . . .
H14 H 0.3811 0.3603 0.2627 0.067 Uiso 1 1 calc R U . . .
C15 C 0.6473(3) 0.5635(3) 0.45033(13) 0.0805(8) Uani 1 1 d . . . . .
H15A H 0.7468 0.5897 0.4608 0.121 Uiso 1 1 calc R U . . .
H15B H 0.6346 0.4919 0.4794 0.121 Uiso 1 1 calc R U . . .
H15C H 0.5867 0.6310 0.4608 0.121 Uiso 1 1 calc R U . . .
C16 C 0.6064(2) 0.3664(2) 0.12603(12) 0.0533(5) Uani 1 1 d . . . . .
C17 C 0.6613(2) 0.4193(2) 0.07160(13) 0.0670(6) Uani 1 1 d . . . . .
H17 H 0.6264 0.4962 0.0524 0.080 Uiso 1 1 calc R U . . .
C18 C 0.7689(3) 0.3581(3) 0.04524(13) 0.0741(7) Uani 1 1 d . . . . .
H18 H 0.8059 0.3941 0.0077 0.089 Uiso 1 1 calc R U . . .
C19 C 0.8225(2) 0.2460(3) 0.07267(13) 0.0666(7) Uani 1 1 d . . . . .
C20 C 0.7658(3) 0.1953(2) 0.12755(14) 0.0720(7) Uani 1 1 d . . . . .
H20 H 0.8011 0.1188 0.1473 0.086 Uiso 1 1 calc R U . . .
C21 C 0.6584(2) 0.2543(2) 0.15394(13) 0.0644(6) Uani 1 1 d . . . . .
H21 H 0.6206 0.2178 0.1911 0.077 Uiso 1 1 calc R U . . .
C22 C 0.9389(3) 0.1795(3) 0.04322(17) 0.0974(10) Uani 1 1 d . . . . .
H22A H 0.9837 0.1177 0.0773 0.146 Uiso 1 1 calc R U . . .
H22B H 1.0104 0.2391 0.0347 0.146 Uiso 1 1 calc R U . . .
H22C H 0.8972 0.1389 -0.0012 0.146 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
N1 C1 1.344(3) . ?
N1 C9 1.421(3) . ?
N1 C16 1.432(3) . ?
O1 C1 1.204(2) . ?
F1 C8 1.210(16) . ?
F2 C8 1.265(14) . ?
F3 C8 1.261(12) . ?
F1' C8 1.330(8) . ?
F2' C8 1.320(6) . ?
F3' C8 1.296(8) . ?
C1 C2 1.489(3) . ?
C2 C7 1.360(3) . ?
C2 C3 1.363(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.346(3) . ?
C5 C6 1.353(3) . ?
C5 C8 1.476(4) . ?
C6 C7 1.368(3) . ?
C9 C14 1.363(3) . ?
C9 C10 1.369(3) . ?
C10 C11 1.355(3) . ?
C11 C12 1.371(3) . ?
C12 C13 1.371(3) . ?
C12 C15 1.488(3) . ?
C13 C14 1.361(3) . ?
C16 C17 1.358(3) . ?
C16 C21 1.358(3) . ?
C17 C18 1.374(3) . ?
C18 C19 1.359(4) . ?
C19 C20 1.365(4) . ?
C19 C22 1.496(3) . ?
C20 C21 1.361(3) . ?

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 N1 C9 123.28(17) . . ?
C1 N1 C16 119.07(17) . . ?
C9 N1 C16 116.75(16) . . ?
O1 C1 N1 122.86(19) . . ?
O1 C1 C2 119.03(19) . . ?
N1 C1 C2 117.99(19) . . ?
C7 C2 C3 119.2(2) . . ?
C7 C2 C1 119.6(2) . . ?
C3 C2 C1 120.77(19) . . ?
C2 C3 C4 120.4(2) . . ?
C5 C4 C3 119.9(2) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 C8 120.3(3) . . ?
C6 C5 C8 119.6(2) . . ?
C5 C6 C7 120.4(2) . . ?
C2 C7 C6 119.9(2) . . ?
F3 C8 F1 113.6(11) . . ?
F3 C8 F2 101.0(12) . . ?
F1 C8 F2 102.1(15) . . ?
F3' C8 F1' 107.0(8) . . ?
F3' C8 F2' 109.9(6) . . ?
F1' C8 F2' 100.8(6) . . ?
F3 C8 C5 110.7(6) . . ?
F1 C8 C5 115.2(8) . . ?
F2 C8 C5 113.0(7) . . ?
F3' C8 C5 112.9(5) . . ?
F1' C8 C5 110.6(4) . . ?
F2' C8 C5 114.7(3) . . ?
C14 C9 C10 119.0(2) . . ?
C14 C9 N1 121.11(19) . . ?
C10 C9 N1 119.9(2) . . ?
C11 C10 C9 120.1(2) . . ?
C10 C11 C12 122.1(2) . . ?
C11 C12 C13 116.7(2) . . ?
C11 C12 C15 121.7(2) . . ?
C13 C12 C15 121.6(2) . . ?
C14 C13 C12 122.0(2) . . ?
C13 C14 C9 120.1(2) . . ?
C17 C16 C21 119.9(2) . . ?
C17 C16 N1 119.7(2) . . ?
C21 C16 N1 120.4(2) . . ?
C16 C17 C18 119.3(2) . . ?
C19 C18 C17 121.6(2) . . ?
C18 C19 C20 117.9(2) . . ?
C18 C19 C22 121.2(3) . . ?
C20 C19 C22 120.9(3) . . ?
C21 C20 C19 121.3(2) . . ?
C16 C21 C20 120.0(2) . . ?

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
C9 N1 C1 O1 -158.6(2) . . . . ?
C16 N1 C1 O1 10.1(3) . . . . ?
C9 N1 C1 C2 25.4(3) . . . . ?
C16 N1 C1 C2 -165.9(2) . . . . ?
O1 C1 C2 C7 46.1(3) . . . . ?
N1 C1 C2 C7 -137.8(2) . . . . ?
O1 C1 C2 C3 -126.6(2) . . . . ?
N1 C1 C2 C3 49.5(3) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 171.8(2) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C8 179.7(3) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C8 C5 C6 C7 179.3(3) . . . . ?
C3 C2 C7 C6 -0.2(4) . . . . ?
C1 C2 C7 C6 -173.0(3) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C4 C5 C8 F3 46.3(17) . . . . ?
C6 C5 C8 F3 -133.3(17) . . . . ?
C4 C5 C8 F1 -84(2) . . . . ?
C6 C5 C8 F1 96(2) . . . . ?
C4 C5 C8 F2 158.8(9) . . . . ?
C6 C5 C8 F2 -20.7(10) . . . . ?
C4 C5 C8 F3' 120.4(11) . . . . ?
C6 C5 C8 F3' -59.1(11) . . . . ?
C4 C5 C8 F1' -119.7(6) . . . . ?
C6 C5 C8 F1' 60.7(6) . . . . ?
C4 C5 C8 F2' -6.6(9) . . . . ?
C6 C5 C8 F2' 173.9(8) . . . . ?
C1 N1 C9 C14 52.8(3) . . . . ?
C16 N1 C9 C14 -116.1(2) . . . . ?
C1 N1 C9 C10 -129.1(2) . . . . ?
C16 N1 C9 C10 61.9(3) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
N1 C9 C10 C11 -177.46(19) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C10 C11 C12 C15 -179.6(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C15 C12 C13 C14 -179.8(2) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
N1 C9 C14 C13 178.01(19) . . . . ?
C1 N1 C16 C17 72.6(3) . . . . ?
C9 N1 C16 C17 -118.0(2) . . . . ?
C1 N1 C16 C21 -108.7(2) . . . . ?
C9 N1 C16 C21 60.7(3) . . . . ?
C21 C16 C17 C18 0.3(4) . . . . ?
N1 C16 C17 C18 178.9(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C17 C18 C19 C22 179.5(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C22 C19 C20 C21 -179.0(2) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
N1 C16 C21 C20 -178.5(2) . . . . ?
C19 C20 C21 C16 -0.5(4) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 1014922'
