# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry 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.
# 
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#  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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          382-383K
_chemical_formula_moiety         'C20 H16 F3 N O2'
_chemical_formula_sum            'C20 H16 F3 N O2'
_chemical_formula_weight         359.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   27.553(3)
_cell_length_b                   7.7658(8)
_cell_length_c                   17.6413(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.441(2)
_cell_angle_gamma                90.00
_cell_volume                     3537.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3071
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.62

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.103
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 The ISOR $F and AFIX 137 for methyl hydrogen atoms are used,
so 18 least-squares restraints used in the refinement.
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8772
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.19
_reflns_number_total             3181
_reflns_number_gt                2470
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1042P)²+2.9927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0061(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3181
_refine_ls_number_parameters     238
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1761
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
N1 N 0.04410(7) 0.7914(2) 0.17979(11) 0.0466(5) Uani 1 1 d . . .
C1 C 0.03402(9) 0.9649(3) 0.17508(13) 0.0485(5) Uani 1 1 d . . .
C2 C -0.01368(9) 0.9893(3) 0.11485(13) 0.0477(5) Uani 1 1 d . . .
C3 C -0.03328(8) 0.8219(3) 0.08356(14) 0.0457(5) Uani 1 1 d . . .
C4 C 0.00299(8) 0.7057(3) 0.12480(13) 0.0470(5) Uani 1 1 d . . .
H4A H 0.0005 0.5870 0.1172 0.056 Uiso 1 1 calc R . .
C5 C -0.08381(9) 0.7723(3) 0.02314(14) 0.0503(6) Uani 1 1 d . . .
C6 C -0.08576(12) 0.6760(4) -0.04388(18) 0.0725(8) Uani 1 1 d . . .
H6A H -0.0552 0.6478 -0.0523 0.087 Uiso 1 1 calc R . .
C7 C -0.13257(15) 0.6217(5) -0.0982(2) 0.0991(12) Uani 1 1 d . . .
H7A H -0.1332 0.5572 -0.1429 0.119 Uiso 1 1 calc R . .
C8 C -0.17746(15) 0.6604(5) -0.0875(3) 0.1017(13) Uani 1 1 d . . .
H8A H -0.2088 0.6219 -0.1243 0.122 Uiso 1 1 calc R . .
C9 C -0.17638(12) 0.7573(6) -0.0217(2) 0.0964(12) Uani 1 1 d . . .
H9A H -0.2072 0.7858 -0.0144 0.116 Uiso 1 1 calc R . .
C10 C -0.12968(10) 0.8129(4) 0.03373(17) 0.0708(8) Uani 1 1 d . . .
H10A H -0.1293 0.8778 0.0782 0.085 Uiso 1 1 calc R . .
C11 C -0.03585(10) 1.1592(3) 0.08703(16) 0.0562(6) Uani 1 1 d . . .
C12 C -0.07592(12) 1.1783(4) 0.00482(18) 0.0748(8) Uani 1 1 d . . .
H12A H -0.0753 1.2939 -0.0141 0.090 Uiso 1 1 calc R . .
H12B H -0.1095 1.1543 0.0074 0.090 Uiso 1 1 calc R . .
H12C H -0.0688 1.0990 -0.0317 0.090 Uiso 1 1 calc R . .
C13 C 0.07033(11) 1.0919(3) 0.22904(16) 0.0657(7) Uani 1 1 d . . .
H13A H 0.0923 1.0348 0.2770 0.079 Uiso 1 1 calc R . .
H13B H 0.0509 1.1804 0.2437 0.079 Uiso 1 1 calc R . .
H13C H 0.0912 1.1425 0.2013 0.079 Uiso 1 1 calc R . .
C14 C 0.08881(8) 0.7049(3) 0.23300(13) 0.0465(5) Uani 1 1 d . . .
C15 C 0.13798(9) 0.7545(3) 0.23820(16) 0.0599(6) Uani 1 1 d . . .
H15A H 0.1424 0.8457 0.2071 0.072 Uiso 1 1 calc R . .
C16 C 0.18066(9) 0.6681(4) 0.28982(17) 0.0657(7) Uani 1 1 d . . .
H16A H 0.2140 0.7012 0.2941 0.079 Uiso 1 1 calc R . .
C17 C 0.17323(9) 0.5333(3) 0.33438(15) 0.0591(6) Uani 1 1 d . . .
C18 C 0.12486(9) 0.4813(3) 0.32970(15) 0.0569(6) Uani 1 1 d . . .
H18A H 0.1206 0.3890 0.3604 0.068 Uiso 1 1 calc R . .
C19 C 0.08256(8) 0.5681(3) 0.27865(14) 0.0515(6) Uani 1 1 d . . .
H19A H 0.0494 0.5343 0.2749 0.062 Uiso 1 1 calc R . .
C20 C 0.23575(19) 0.3187(8) 0.3708(3) 0.1302(19) Uani 1 1 d . . .
O1 O -0.02091(9) 1.2876(2) 0.12882(13) 0.0834(7) Uani 1 1 d . . .
O2 O 0.21719(7) 0.4533(3) 0.39076(12) 0.0816(6) Uani 1 1 d . . .
F1 F 0.20562(17) 0.1980(5) 0.3457(5) 0.325(5) Uani 1 1 d U . .
F2 F 0.2491(2) 0.3532(10) 0.3091(3) 0.316(4) Uani 1 1 d U . .
F3 F 0.27725(10) 0.2654(4) 0.42424(19) 0.1624(13) Uani 1 1 d 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 1.372(3) . ?
N1 C4 1.379(3) . ?
N1 C14 1.429(3) . ?
C1 C2 1.385(3) . ?
C1 C13 1.488(3) . ?
C2 C3 1.442(3) . ?
C2 C11 1.464(3) . ?
C3 C4 1.354(3) . ?
C3 C5 1.479(3) . ?
C4 H4A 0.9300 . ?
C5 C10 1.377(3) . ?
C5 C6 1.384(4) . ?
C6 C7 1.377(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.348(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.375(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.385(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 O1 1.223(3) . ?
C11 C12 1.492(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.380(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.384(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.366(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.367(3) . ?
C17 O2 1.415(3) . ?
C18 C19 1.375(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 F1 1.227(7) . ?
C20 O2 1.266(5) . ?
C20 F3 1.271(4) . ?
C20 F2 1.292(7) . ?

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 C4 109.42(18) . . ?
C1 N1 C14 127.66(18) . . ?
C4 N1 C14 122.91(18) . . ?
N1 C1 C2 107.38(18) . . ?
N1 C1 C13 122.4(2) . . ?
C2 C1 C13 130.2(2) . . ?
C1 C2 C3 107.37(19) . . ?
C1 C2 C11 123.6(2) . . ?
C3 C2 C11 128.9(2) . . ?
C4 C3 C2 106.73(19) . . ?
C4 C3 C5 123.09(19) . . ?
C2 C3 C5 130.0(2) . . ?
C3 C4 N1 109.08(18) . . ?
C3 C4 H4A 125.5 . . ?
N1 C4 H4A 125.5 . . ?
C10 C5 C6 118.4(2) . . ?
C10 C5 C3 121.3(2) . . ?
C6 C5 C3 120.2(2) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C5 C10 C9 120.2(3) . . ?
C5 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
O1 C11 C2 121.3(2) . . ?
O1 C11 C12 118.9(2) . . ?
C2 C11 C12 119.7(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 119.7(2) . . ?
C19 C14 N1 119.38(19) . . ?
C15 C14 N1 120.9(2) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C16 C17 C18 122.0(2) . . ?
C16 C17 O2 118.5(2) . . ?
C18 C17 O2 119.3(3) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18A 120.7 . . ?
C19 C18 H18A 120.7 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19A 119.7 . . ?
C14 C19 H19A 119.7 . . ?
F1 C20 O2 116.3(5) . . ?
F1 C20 F3 109.8(5) . . ?
O2 C20 F3 114.1(4) . . ?
F1 C20 F2 102.2(6) . . ?
O2 C20 F2 108.9(6) . . ?
F3 C20 F2 104.2(5) . . ?
C20 O2 C17 119.8(3) . . ?

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
C4 N1 C1 C2 -1.4(2) . . . . ?
C14 N1 C1 C2 179.83(19) . . . . ?
C4 N1 C1 C13 177.8(2) . . . . ?
C14 N1 C1 C13 -1.0(3) . . . . ?
N1 C1 C2 C3 1.2(2) . . . . ?
C13 C1 C2 C3 -177.8(2) . . . . ?
N1 C1 C2 C11 -174.6(2) . . . . ?
C13 C1 C2 C11 6.4(4) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C11 C2 C3 C4 174.8(2) . . . . ?
C1 C2 C3 C5 175.1(2) . . . . ?
C11 C2 C3 C5 -9.4(4) . . . . ?
C2 C3 C4 N1 -0.2(2) . . . . ?
C5 C3 C4 N1 -176.3(2) . . . . ?
C1 N1 C4 C3 1.0(2) . . . . ?
C14 N1 C4 C3 179.84(19) . . . . ?
C4 C3 C5 C10 118.0(3) . . . . ?
C2 C3 C5 C10 -57.2(3) . . . . ?
C4 C3 C5 C6 -58.9(3) . . . . ?
C2 C3 C5 C6 126.0(3) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C3 C5 C6 C7 176.6(3) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C6 C5 C10 C9 0.2(4) . . . . ?
C3 C5 C10 C9 -176.7(2) . . . . ?
C8 C9 C10 C5 0.4(5) . . . . ?
C1 C2 C11 O1 -20.2(4) . . . . ?
C3 C2 C11 O1 165.0(2) . . . . ?
C1 C2 C11 C12 157.2(2) . . . . ?
C3 C2 C11 C12 -17.6(4) . . . . ?
C1 N1 C14 C19 128.3(2) . . . . ?
C4 N1 C14 C19 -50.3(3) . . . . ?
C1 N1 C14 C15 -52.8(3) . . . . ?
C4 N1 C14 C15 128.5(2) . . . . ?
C19 C14 C15 C16 -0.8(4) . . . . ?
N1 C14 C15 C16 -179.6(2) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C15 C16 C17 O2 -176.0(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
O2 C17 C18 C19 175.6(2) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
N1 C14 C19 C18 179.3(2) . . . . ?
F1 C20 O2 C17 -55.3(8) . . . . ?
F3 C20 O2 C17 175.3(4) . . . . ?
F2 C20 O2 C17 59.4(6) . . . . ?
C16 C17 O2 C20 -95.9(5) . . . . ?
C18 C17 O2 C20 88.2(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
C4 H4A O1 0.93 2.43 3.318(3) 160.9 1_545

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 949005'
