# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1540172'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 F3 O3'
_chemical_formula_weight         286.24

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   16.2998(10)
_cell_length_b                   10.3533(6)
_cell_length_c                   7.8903(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1331.54(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2905
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      24.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20606
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3066
_reflns_number_gt                2102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(10)
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14567(15) 0.2479(2) 0.3465(4) 0.0440(6) Uani 1 1 d . . .
H1A H 0.0914 0.2675 0.3722 0.053 Uiso 1 1 calc R . .
F1 F 0.02023(10) -0.24336(18) 0.2268(3) 0.0845(7) Uani 1 1 d . . .
O3 O 0.31579(11) -0.0813(2) 0.1156(3) 0.0681(6) Uani 1 1 d . . .
C8 C 0.16596(14) -0.0758(2) 0.1296(3) 0.0406(5) Uani 1 1 d . . .
H8A H 0.1529 -0.0697 0.0087 0.049 Uiso 1 1 calc R . .
C7 C 0.25332(15) -0.0243(2) 0.1556(3) 0.0441(6) Uani 1 1 d . . .
O2 O 0.11495(15) 0.46711(19) 0.5306(3) 0.0669(6) Uani 1 1 d . . .
O1 O 0.23839(16) 0.5493(2) 0.4723(4) 0.0831(8) Uani 1 1 d . . .
F3 F 0.08864(12) -0.41225(17) 0.1624(4) 0.0926(8) Uani 1 1 d . . .
C4 C 0.31009(15) 0.1915(3) 0.2721(3) 0.0498(7) Uani 1 1 d . . .
H4A H 0.3645 0.1718 0.2476 0.060 Uiso 1 1 calc R . .
C5 C 0.24738(14) 0.1037(2) 0.2336(3) 0.0398(5) Uani 1 1 d . . .
C2 C 0.20774(16) 0.3356(3) 0.3829(3) 0.0468(6) Uani 1 1 d . . .
C12 C 0.16230(15) -0.2178(2) 0.1807(4) 0.0495(7) Uani 1 1 d . . .
H12A H 0.2074 -0.2629 0.1266 0.059 Uiso 1 1 calc R . .
H12B H 0.1703 -0.2239 0.3022 0.059 Uiso 1 1 calc R . .
C3 C 0.28993(16) 0.3068(3) 0.3463(4) 0.0518(7) Uani 1 1 d . . .
H3A H 0.3308 0.3662 0.3724 0.062 Uiso 1 1 calc R . .
C9 C 0.10946(13) 0.0198(2) 0.2265(3) 0.0394(6) Uani 1 1 d . . .
H9A H 0.0916 -0.0218 0.3318 0.047 Uiso 1 1 calc R . .
C6 C 0.16552(15) 0.1311(2) 0.2717(3) 0.0386(5) Uani 1 1 d . . .
F2 F 0.06360(13) -0.2689(2) -0.0247(3) 0.0899(7) Uani 1 1 d . . .
C13 C 0.1904(2) 0.4622(3) 0.4653(4) 0.0555(7) Uani 1 1 d . . .
C10 C 0.03333(15) 0.0623(3) 0.1286(5) 0.0583(7) Uani 1 1 d . . .
H10A H 0.0018 0.1207 0.1969 0.087 Uiso 1 1 calc R . .
H10B H 0.0006 -0.0120 0.1014 0.087 Uiso 1 1 calc R . .
H10C H 0.0497 0.1048 0.0259 0.087 Uiso 1 1 calc R . .
C11 C 0.08473(17) -0.2843(3) 0.1362(5) 0.0572(7) Uani 1 1 d . . .
C14 C 0.0942(3) 0.5832(3) 0.6220(6) 0.0885(12) Uani 1 1 d . . .
H14A H 0.0391 0.5765 0.6642 0.133 Uiso 1 1 calc R . .
H14B H 0.0982 0.6562 0.5475 0.133 Uiso 1 1 calc R . .
H14C H 0.1314 0.5941 0.7152 0.133 Uiso 1 1 calc R . .


_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
C1 C6 1.384(3) . ?
C1 C2 1.389(4) . ?
C1 H1A 0.9300 . ?
F1 C11 1.340(4) . ?
O3 C7 1.218(3) . ?
C8 C12 1.526(3) . ?
C8 C7 1.534(3) . ?
C8 C9 1.552(3) . ?
C8 H8A 0.9800 . ?
C7 C5 1.465(3) . ?
O2 C13 1.334(4) . ?
O2 C14 1.442(4) . ?
O1 C13 1.196(4) . ?
F3 C11 1.343(3) . ?
C4 C3 1.370(4) . ?
C4 C5 1.401(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.397(3) . ?
C2 C3 1.402(4) . ?
C2 C13 1.490(4) . ?
C12 C11 1.482(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 H3A 0.9300 . ?
C9 C6 1.514(3) . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9800 . ?
F2 C11 1.325(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C6 C1 C2 119.3(2) . . ?
C6 C1 H1A 120.4 . . ?
C2 C1 H1A 120.4 . . ?
C12 C8 C7 109.6(2) . . ?
C12 C8 C9 117.5(2) . . ?
C7 C8 C9 105.30(19) . . ?
C12 C8 H8A 108.0 . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
O3 C7 C5 127.0(2) . . ?
O3 C7 C8 125.0(2) . . ?
C5 C7 C8 107.99(19) . . ?
C13 O2 C14 116.2(3) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 C7 129.0(2) . . ?
C6 C5 C7 109.7(2) . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 C13 121.8(2) . . ?
C3 C2 C13 117.3(2) . . ?
C11 C12 C8 114.7(2) . . ?
C11 C12 H12A 108.6 . . ?
C8 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C8 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C6 C9 C10 113.0(2) . . ?
C6 C9 C8 104.07(18) . . ?
C10 C9 C8 114.6(2) . . ?
C6 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C8 C9 H9A 108.3 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 C9 128.7(2) . . ?
C5 C6 C9 111.8(2) . . ?
O1 C13 O2 123.8(3) . . ?
O1 C13 C2 124.0(3) . . ?
O2 C13 C2 112.2(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 C11 F1 105.6(3) . . ?
F2 C11 F3 106.1(3) . . ?
F1 C11 F3 105.5(3) . . ?
F2 C11 C12 113.1(3) . . ?
F1 C11 C12 113.4(3) . . ?
F3 C11 C12 112.4(2) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C12 C8 C7 O3 43.7(4) . . . . ?
C9 C8 C7 O3 170.9(3) . . . . ?
C12 C8 C7 C5 -137.0(2) . . . . ?
C9 C8 C7 C5 -9.7(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C7 -179.8(3) . . . . ?
O3 C7 C5 C4 3.5(5) . . . . ?
C8 C7 C5 C4 -175.8(3) . . . . ?
O3 C7 C5 C6 -175.5(3) . . . . ?
C8 C7 C5 C6 5.1(3) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C6 C1 C2 C13 -179.2(3) . . . . ?
C7 C8 C12 C11 -170.8(2) . . . . ?
C9 C8 C12 C11 69.2(3) . . . . ?
C5 C4 C3 C2 0.1(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C13 C2 C3 C4 179.3(3) . . . . ?
C12 C8 C9 C6 132.6(2) . . . . ?
C7 C8 C9 C6 10.3(2) . . . . ?
C12 C8 C9 C10 -103.4(3) . . . . ?
C7 C8 C9 C10 134.3(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C9 177.6(3) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C7 C5 C6 C1 -179.9(2) . . . . ?
C4 C5 C6 C9 -177.2(2) . . . . ?
C7 C5 C6 C9 1.9(3) . . . . ?
C10 C9 C6 C1 49.1(3) . . . . ?
C8 C9 C6 C1 174.1(2) . . . . ?
C10 C9 C6 C5 -132.8(2) . . . . ?
C8 C9 C6 C5 -7.9(3) . . . . ?
C14 O2 C13 O1 -3.6(5) . . . . ?
C14 O2 C13 C2 176.4(3) . . . . ?
C1 C2 C13 O1 -166.3(3) . . . . ?
C3 C2 C13 O1 15.0(5) . . . . ?
C1 C2 C13 O2 13.7(4) . . . . ?
C3 C2 C13 O2 -165.1(3) . . . . ?
C8 C12 C11 F2 51.3(3) . . . . ?
C8 C12 C11 F1 -69.0(4) . . . . ?
C8 C12 C11 F3 171.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038

