# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd214423

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 F3 O'
_chemical_formula_weight         380.39

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.3668(8)
_cell_length_b                   9.6287(15)
_cell_length_c                   18.804(3)
_cell_angle_alpha                82.874(3)
_cell_angle_beta                 86.417(4)
_cell_angle_gamma                82.471(4)
_cell_volume                     954.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1435
_cell_measurement_theta_min      4.371
_cell_measurement_theta_max      46.896

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4299
_exptl_absorpt_correction_T_max  0.7457
_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            5822
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3747
_reflns_number_gt                2482
_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)+(0.1140P)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         3747
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.006
_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
F1 F 0.3630(4) 0.62290(18) 0.31674(9) 0.1026(6) Uani 1 1 d . . . . .
F2 F 0.2402(4) 0.60981(19) 0.42683(10) 0.1142(7) Uani 1 1 d . . . . .
F3 F 0.6044(3) 0.5232(2) 0.39550(11) 0.1093(7) Uani 1 1 d . . . . .
O1 O 0.1594(4) 0.6289(2) 0.03387(9) 0.0808(6) Uani 1 1 d . . . . .
C1 C 0.1945(4) 0.3530(2) 0.31767(11) 0.0477(5) Uani 1 1 d . . . . .
C2 C 0.2731(4) 0.4002(2) 0.37575(12) 0.0549(6) Uani 1 1 d . . . . .
C3 C 0.2697(5) 0.3101(3) 0.44847(13) 0.0684(7) Uani 1 1 d . . . . .
H3A H 0.3900 0.3382 0.4786 0.082 Uiso 1 1 calc R U . . .
H3B H 0.1039 0.3252 0.4720 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3351(5) 0.1561(3) 0.43934(13) 0.0672(7) Uani 1 1 d . . . . .
H4A H 0.3130 0.0995 0.4852 0.081 Uiso 1 1 calc R U . . .
H4B H 0.5101 0.1383 0.4229 0.081 Uiso 1 1 calc R U . . .
C5 C 0.1692(4) 0.1145(2) 0.38565(11) 0.0547(6) Uani 1 1 d . . . . .
C6 C 0.1059(4) 0.2120(2) 0.32548(11) 0.0474(5) Uani 1 1 d . . . . .
C7 C -0.0384(4) 0.1734(2) 0.27451(11) 0.0488(5) Uani 1 1 d . . . . .
H7 H -0.0780 0.2375 0.2344 0.059 Uiso 1 1 calc R U . . .
C8 C -0.1268(4) 0.0426(2) 0.28063(12) 0.0506(5) Uani 1 1 d . . . . .
C9 C -0.0626(5) -0.0511(3) 0.34115(14) 0.0626(6) Uani 1 1 d . . . . .
H9 H -0.1189 -0.1394 0.3473 0.075 Uiso 1 1 calc R U . . .
C10 C 0.0828(5) -0.0150(2) 0.39197(13) 0.0646(6) Uani 1 1 d . . . . .
H10 H 0.1239 -0.0799 0.4317 0.077 Uiso 1 1 calc R U . . .
C11 C -0.2798(4) 0.0058(2) 0.22421(12) 0.0536(6) Uani 1 1 d . . . . .
C12 C -0.2510(5) 0.0630(3) 0.15351(13) 0.0665(7) Uani 1 1 d . . . . .
H12 H -0.1302 0.1237 0.1408 0.080 Uiso 1 1 calc R U . . .
C13 C -0.3969(6) 0.0321(3) 0.10159(15) 0.0828(8) Uani 1 1 d . . . . .
H13 H -0.3760 0.0733 0.0545 0.099 Uiso 1 1 calc R U . . .
C14 C -0.5731(5) -0.0590(3) 0.11873(18) 0.0839(9) Uani 1 1 d . . . . .
H14 H -0.6720 -0.0799 0.0836 0.101 Uiso 1 1 calc R U . . .
C15 C -0.6020(5) -0.1189(3) 0.18812(17) 0.0786(8) Uani 1 1 d . . . . .
H15 H -0.7193 -0.1820 0.2001 0.094 Uiso 1 1 calc R U . . .
C16 C -0.4589(5) -0.0862(3) 0.24004(15) 0.0671(7) Uani 1 1 d . . . . .
H16 H -0.4825 -0.1268 0.2871 0.080 Uiso 1 1 calc R U . . .
C17 C 0.1841(4) 0.4342(2) 0.24408(11) 0.0441(5) Uani 1 1 d . . . . .
C18 C -0.0122(4) 0.5359(2) 0.22461(12) 0.0548(6) Uani 1 1 d . . . . .
H18 H -0.1380 0.5598 0.2588 0.066 Uiso 1 1 calc R U . . .
C19 C -0.0271(4) 0.6034(2) 0.15537(12) 0.0582(6) Uani 1 1 d . . . . .
H19 H -0.1613 0.6722 0.1435 0.070 Uiso 1 1 calc R U . . .
C20 C 0.1564(4) 0.5687(2) 0.10424(11) 0.0552(6) Uani 1 1 d . . . . .
C21 C 0.3533(4) 0.4674(3) 0.12264(13) 0.0672(7) Uani 1 1 d . . . . .
H21 H 0.4794 0.4439 0.0884 0.081 Uiso 1 1 calc R U . . .
C22 C 0.3650(4) 0.4005(3) 0.19141(12) 0.0620(6) Uani 1 1 d . . . . .
H22 H 0.4981 0.3308 0.2028 0.074 Uiso 1 1 calc R U . . .
C23 C -0.0620(6) 0.7131(3) 0.00983(16) 0.0914(9) Uani 1 1 d . . . . .
H23A H -0.2039 0.6622 0.0222 0.137 Uiso 1 1 calc R U . . .
H23B H -0.0471 0.7359 -0.0413 0.137 Uiso 1 1 calc R U . . .
H23C H -0.0853 0.7985 0.0322 0.137 Uiso 1 1 calc R U . . .
C24 C 0.3624(5) 0.5380(3) 0.37762(13) 0.0667(7) Uani 1 1 d . . . . .


_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 C24 1.321(3) . ?
F2 C24 1.314(3) . ?
F3 C24 1.347(3) . ?
O1 C20 1.377(3) . ?
O1 C23 1.413(3) . ?
C1 C2 1.344(3) . ?
C1 C6 1.484(3) . ?
C1 C17 1.503(3) . ?
C2 C24 1.474(3) . ?
C2 C3 1.526(3) . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.509(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.376(3) . ?
C5 C6 1.406(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.392(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(3) . ?
C8 C11 1.484(3) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 C16 1.386(3) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 C22 1.381(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(3) . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C20 O1 C23 117.3(2) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C17 124.78(19) . . ?
C6 C1 C17 116.32(17) . . ?
C1 C2 C24 125.8(2) . . ?
C1 C2 C3 120.4(2) . . ?
C24 C2 C3 113.77(19) . . ?
C4 C3 C2 110.51(19) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 110.3(2) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 118.7(2) . . ?
C10 C5 C4 123.1(2) . . ?
C6 C5 C4 118.1(2) . . ?
C7 C6 C5 118.73(19) . . ?
C7 C6 C1 121.41(19) . . ?
C5 C6 C1 119.86(19) . . ?
C6 C7 C8 122.8(2) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 C11 120.8(2) . . ?
C9 C8 C11 122.2(2) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C5 C10 C9 121.8(2) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C16 117.0(2) . . ?
C12 C11 C8 121.3(2) . . ?
C16 C11 C8 121.7(2) . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C18 C17 C22 117.3(2) . . ?
C18 C17 C1 122.31(18) . . ?
C22 C17 C1 120.19(19) . . ?
C17 C18 C19 121.6(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 O1 116.1(2) . . ?
C19 C20 O1 124.5(2) . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F2 C24 F1 107.6(2) . . ?
F2 C24 F3 104.3(2) . . ?
F1 C24 F3 102.9(2) . . ?
F2 C24 C2 112.7(2) . . ?
F1 C24 C2 116.8(2) . . ?
F3 C24 C2 111.5(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
C6 C1 C2 C24 -178.9(2) . . . . ?
C17 C1 C2 C24 -0.1(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C17 C1 C2 C3 178.5(2) . . . . ?
C1 C2 C3 C4 36.0(3) . . . . ?
C24 C2 C3 C4 -145.2(2) . . . . ?
C2 C3 C4 C5 -52.6(3) . . . . ?
C3 C4 C5 C10 -144.1(2) . . . . ?
C3 C4 C5 C6 37.6(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 C7 177.65(19) . . . . ?
C10 C5 C6 C1 179.42(19) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C2 C1 C6 C7 162.2(2) . . . . ?
C17 C1 C6 C7 -16.7(3) . . . . ?
C2 C1 C6 C5 -18.0(3) . . . . ?
C17 C1 C6 C5 163.18(18) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C1 C6 C7 C8 -179.25(18) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C6 C7 C8 C11 -179.62(19) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C11 C8 C9 C10 178.9(2) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C4 C5 C10 C9 -178.2(2) . . . . ?
C8 C9 C10 C5 0.5(4) . . . . ?
C7 C8 C11 C12 29.0(3) . . . . ?
C9 C8 C11 C12 -150.2(2) . . . . ?
C7 C8 C11 C16 -150.4(2) . . . . ?
C9 C8 C11 C16 30.3(3) . . . . ?
C16 C11 C12 C13 1.3(4) . . . . ?
C8 C11 C12 C13 -178.2(2) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C15 C16 C11 -0.9(4) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C8 C11 C16 C15 179.2(2) . . . . ?
C2 C1 C17 C18 -81.7(3) . . . . ?
C6 C1 C17 C18 97.1(2) . . . . ?
C2 C1 C17 C22 103.5(3) . . . . ?
C6 C1 C17 C22 -77.7(2) . . . . ?
C22 C17 C18 C19 -0.9(3) . . . . ?
C1 C17 C18 C19 -175.84(18) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C20 O1 179.8(2) . . . . ?
C23 O1 C20 C21 168.3(2) . . . . ?
C23 O1 C20 C19 -11.7(4) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
O1 C20 C21 C22 -179.3(2) . . . . ?
C20 C21 C22 C17 -1.2(4) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C1 C17 C22 C21 176.4(2) . . . . ?
C1 C2 C24 F2 125.8(3) . . . . ?
C3 C2 C24 F2 -52.9(3) . . . . ?
C1 C2 C24 F1 0.6(4) . . . . ?
C3 C2 C24 F1 -178.1(2) . . . . ?
C1 C2 C24 F3 -117.3(3) . . . . ?
C3 C2 C24 F3 64.0(3) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1018298'
