# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1042327'
_audit_update_record             
;
2015-01-07 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 F6 N O3'
_chemical_formula_sum            'C18 H11 F6 N O3'
_chemical_formula_weight         403.28

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  '
_symmetry_space_group_name_Hall  '-C 2yc'

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                   32.403(8)
_cell_length_b                   6.8959(17)
_cell_length_c                   15.250(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.030(4)
_cell_angle_gamma                90.00
_cell_volume                     3382.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4354
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.19
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9419
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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_decay_%        ?
_diffrn_reflns_number            10886
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3860
_reflns_number_gt                2872
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3860
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
C1 C 0.31199(5) 1.0514(2) 0.02148(10) 0.0470(4) Uani 1 1 d . . .
C2 C 0.26930(5) 1.0157(2) 0.04188(10) 0.0447(4) Uani 1 1 d . . .
C3 C 0.23327(6) 0.9867(2) -0.01518(12) 0.0554(4) Uani 1 1 d . . .
H3 H 0.2335 0.9912 -0.0761 0.066 Uiso 1 1 calc R . .
C4 C 0.19694(6) 0.9507(3) 0.02100(13) 0.0618(5) Uani 1 1 d . . .
H4 H 0.1724 0.9308 -0.0162 0.074 Uiso 1 1 calc R . .
C5 C 0.19648(6) 0.9438(3) 0.11103(13) 0.0609(5) Uani 1 1 d . . .
H5 H 0.1719 0.9185 0.1346 0.073 Uiso 1 1 calc R . .
C6 C 0.23285(5) 0.9746(3) 0.16583(11) 0.0525(4) Uani 1 1 d . . .
C7 C 0.26967(5) 1.0111(2) 0.13278(9) 0.0434(3) Uani 1 1 d . . .
C8 C 0.31288(5) 1.0434(2) 0.17945(9) 0.0432(3) Uani 1 1 d . . .
H8 H 0.3139 1.1636 0.2139 0.052 Uiso 1 1 calc R . .
C9 C 0.32800(5) 0.8739(3) 0.23840(10) 0.0488(4) Uani 1 1 d . . .
H9A H 0.3076 0.8472 0.2783 0.059 Uiso 1 1 calc R . .
H9B H 0.3299 0.7599 0.2018 0.059 Uiso 1 1 calc R . .
C10 C 0.36964(5) 0.9071(3) 0.29226(10) 0.0507(4) Uani 1 1 d . . .
C11 C 0.42549(7) 0.7444(4) 0.37538(17) 0.0887(7) Uani 1 1 d . . .
H11A H 0.4246 0.8418 0.4210 0.106 Uiso 1 1 calc R . .
H11B H 0.4477 0.7771 0.3408 0.106 Uiso 1 1 calc R . .
C12 C 0.43272(9) 0.5525(5) 0.41538(19) 0.1047(9) Uani 1 1 d . . .
H12A H 0.4111 0.5237 0.4512 0.157 Uiso 1 1 calc R . .
H12B H 0.4592 0.5513 0.4515 0.157 Uiso 1 1 calc R . .
H12C H 0.4327 0.4567 0.3697 0.157 Uiso 1 1 calc R . .
C13 C 0.37935(5) 1.0995(2) 0.11033(10) 0.0489(4) Uani 1 1 d . . .
C14 C 0.39648(6) 1.2724(3) 0.14290(11) 0.0573(4) Uani 1 1 d . . .
C15 C 0.43892(7) 1.3019(3) 0.15367(14) 0.0721(6) Uani 1 1 d . . .
C16 C 0.46467(6) 1.1582(4) 0.13033(15) 0.0777(6) Uani 1 1 d . . .
C17 C 0.44855(7) 0.9863(4) 0.09645(16) 0.0755(6) Uani 1 1 d . . .
C18 C 0.40618(6) 0.9581(3) 0.08705(13) 0.0597(4) Uani 1 1 d . . .
F1 F 0.23227(3) 0.9694(2) 0.25504(7) 0.0730(4) Uani 1 1 d . . .
F2 F 0.37147(4) 1.41206(17) 0.16631(9) 0.0789(4) Uani 1 1 d . . .
F3 F 0.45465(5) 1.4696(2) 0.18578(11) 0.1105(6) Uani 1 1 d . . .
F4 F 0.50575(4) 1.1846(3) 0.14083(12) 0.1175(6) Uani 1 1 d . . .
F5 F 0.47383(4) 0.8468(3) 0.07274(13) 0.1169(6) Uani 1 1 d . . .
F6 F 0.39126(4) 0.78750(19) 0.05585(10) 0.0838(4) Uani 1 1 d . . .
N1 N 0.33624(4) 1.0667(2) 0.10260(8) 0.0477(3) Uani 1 1 d . . .
O1 O 0.32482(5) 1.0669(2) -0.04940(8) 0.0665(4) Uani 1 1 d . . .
O2 O 0.38495(5) 1.0623(2) 0.30959(9) 0.0703(4) Uani 1 1 d . . .
O3 O 0.38606(4) 0.7380(2) 0.31908(9) 0.0649(4) 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
C1 O1 1.209(2) . ?
C1 N1 1.386(2) . ?
C1 C2 1.475(2) . ?
C2 C3 1.383(2) . ?
C2 C7 1.385(2) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(2) . ?
C5 H5 0.9300 . ?
C6 F1 1.363(2) . ?
C6 C7 1.374(2) . ?
C7 C8 1.507(2) . ?
C8 N1 1.4798(19) . ?
C8 C9 1.519(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.509(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.196(2) . ?
C10 O3 1.325(2) . ?
C11 O3 1.450(2) . ?
C11 C12 1.464(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.381(3) . ?
C13 C14 1.382(2) . ?
C13 N1 1.406(2) . ?
C14 F2 1.335(2) . ?
C14 C15 1.380(3) . ?
C15 F3 1.333(2) . ?
C15 C16 1.370(4) . ?
C16 F4 1.333(2) . ?
C16 C17 1.371(4) . ?
C17 F5 1.342(3) . ?
C17 C18 1.377(3) . ?
C18 F6 1.337(2) . ?

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
O1 C1 N1 124.87(16) . . ?
O1 C1 C2 129.56(15) . . ?
N1 C1 C2 105.57(13) . . ?
C3 C2 C7 121.98(16) . . ?
C3 C2 C1 129.26(15) . . ?
C7 C2 C1 108.74(13) . . ?
C4 C3 C2 118.01(17) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 C3 121.22(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.22(17) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
F1 C6 C7 119.30(14) . . ?
F1 C6 C5 119.14(16) . . ?
C7 C6 C5 121.55(16) . . ?
C6 C7 C2 118.02(14) . . ?
C6 C7 C8 130.68(14) . . ?
C2 C7 C8 111.28(13) . . ?
N1 C8 C7 100.23(11) . . ?
N1 C8 C9 113.14(13) . . ?
C7 C8 C9 112.29(12) . . ?
N1 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
C9 C8 H8 110.3 . . ?
C10 C9 C8 114.05(14) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O2 C10 O3 125.41(16) . . ?
O2 C10 C9 125.12(17) . . ?
O3 C10 C9 109.45(15) . . ?
O3 C11 C12 107.7(2) . . ?
O3 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O3 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
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 . . ?
C18 C13 C14 117.64(16) . . ?
C18 C13 N1 121.01(15) . . ?
C14 C13 N1 121.34(16) . . ?
F2 C14 C15 119.39(17) . . ?
F2 C14 C13 119.24(16) . . ?
C15 C14 C13 121.35(19) . . ?
F3 C15 C16 120.4(2) . . ?
F3 C15 C14 120.1(2) . . ?
C16 C15 C14 119.50(19) . . ?
F4 C16 C15 120.1(2) . . ?
F4 C16 C17 119.5(2) . . ?
C15 C16 C17 120.48(19) . . ?
F5 C17 C16 120.3(2) . . ?
F5 C17 C18 120.3(2) . . ?
C16 C17 C18 119.4(2) . . ?
F6 C18 C17 118.29(18) . . ?
F6 C18 C13 120.07(16) . . ?
C17 C18 C13 121.64(19) . . ?
C1 N1 C13 122.42(13) . . ?
C1 N1 C8 114.17(13) . . ?
C13 N1 C8 123.40(12) . . ?
C10 O3 C11 116.58(17) . . ?

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
O1 C1 C2 C3 1.5(3) . . . . ?
N1 C1 C2 C3 -178.95(16) . . . . ?
O1 C1 C2 C7 -179.49(17) . . . . ?
N1 C1 C2 C7 0.01(16) . . . . ?
C7 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 C4 178.31(16) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 F1 179.44(16) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
F1 C6 C7 C2 -179.96(14) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
F1 C6 C7 C8 2.0(3) . . . . ?
C5 C6 C7 C8 -178.15(16) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C1 C2 C7 C6 -178.45(14) . . . . ?
C3 C2 C7 C8 178.99(14) . . . . ?
C1 C2 C7 C8 -0.07(17) . . . . ?
C6 C7 C8 N1 178.21(16) . . . . ?
C2 C7 C8 N1 0.09(15) . . . . ?
C6 C7 C8 C9 57.8(2) . . . . ?
C2 C7 C8 C9 -120.28(14) . . . . ?
N1 C8 C9 C10 72.28(17) . . . . ?
C7 C8 C9 C10 -175.14(13) . . . . ?
C8 C9 C10 O2 20.9(2) . . . . ?
C8 C9 C10 O3 -160.62(14) . . . . ?
C18 C13 C14 F2 -179.79(16) . . . . ?
N1 C13 C14 F2 -0.9(2) . . . . ?
C18 C13 C14 C15 -1.4(3) . . . . ?
N1 C13 C14 C15 177.49(16) . . . . ?
F2 C14 C15 F3 -1.1(3) . . . . ?
C13 C14 C15 F3 -179.54(16) . . . . ?
F2 C14 C15 C16 179.49(18) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
F3 C15 C16 F4 0.9(3) . . . . ?
C14 C15 C16 F4 -179.66(18) . . . . ?
F3 C15 C16 C17 -179.3(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
F4 C16 C17 F5 -1.0(4) . . . . ?
C15 C16 C17 F5 179.2(2) . . . . ?
F4 C16 C17 C18 178.9(2) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
F5 C17 C18 F6 1.5(3) . . . . ?
C16 C17 C18 F6 -178.40(19) . . . . ?
F5 C17 C18 C13 -179.6(2) . . . . ?
C16 C17 C18 C13 0.5(3) . . . . ?
C14 C13 C18 F6 179.45(15) . . . . ?
N1 C13 C18 F6 0.6(3) . . . . ?
C14 C13 C18 C17 0.6(3) . . . . ?
N1 C13 C18 C17 -178.27(18) . . . . ?
O1 C1 N1 C13 -1.0(2) . . . . ?
C2 C1 N1 C13 179.42(14) . . . . ?
O1 C1 N1 C8 179.58(16) . . . . ?
C2 C1 N1 C8 0.05(17) . . . . ?
C18 C13 N1 C1 -69.5(2) . . . . ?
C14 C13 N1 C1 111.69(17) . . . . ?
C18 C13 N1 C8 109.81(18) . . . . ?
C14 C13 N1 C8 -69.0(2) . . . . ?
C7 C8 N1 C1 -0.08(16) . . . . ?
C9 C8 N1 C1 119.67(14) . . . . ?
C7 C8 N1 C13 -179.45(14) . . . . ?
C9 C8 N1 C13 -59.69(19) . . . . ?
O2 C10 O3 C11 1.2(3) . . . . ?
C9 C10 O3 C11 -177.27(17) . . . . ?
C12 C11 O3 C10 165.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.097
