# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 F4 N O2'
_chemical_formula_weight         361.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.3016(3)
_cell_length_b                   12.1040(4)
_cell_length_c                   16.4292(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.436(3)
_cell_angle_gamma                90.00
_cell_volume                     1632.99(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      67.05

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8020
_exptl_absorpt_correction_T_max  0.8437
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_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            14160
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         67.05
_reflns_number_total             2895
_reflns_number_gt                2291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.1159P)²+0.4540P] 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         2895
_refine_ls_number_parameters     212
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2274
_refine_ls_wR_factor_gt          0.2105
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.154
_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
F1 F 0.0971(2) 0.63684(19) 0.60812(11) 0.0984(6) Uani 1 1 d . . .
F2 F -0.0756(3) 0.8211(2) 0.57377(15) 0.1126(7) Uani 1 1 d . . .
F3 F -0.1290(3) 0.9013(2) 0.41875(16) 0.1149(8) Uani 1 1 d . . .
F4 F -0.0084(3) 0.7934(2) 0.29708(13) 0.1127(8) Uani 1 1 d U . .
O1 O 0.4037(3) 0.2590(2) 0.70545(14) 0.0914(7) Uani 1 1 d . . .
O2 O 0.5842(3) 0.3976(2) 0.71824(15) 0.1080(9) Uani 1 1 d U . .
C1 C 0.3041(3) 0.4510(3) 0.44137(17) 0.0742(8) Uani 1 1 d . . .
H1 H 0.2975 0.4730 0.3867 0.089 Uiso 1 1 calc R . .
C2 C 0.2306(3) 0.5133(2) 0.49097(17) 0.0721(7) Uani 1 1 d . . .
H2 H 0.2394 0.4905 0.5455 0.087 Uiso 1 1 calc R . .
N1 N 0.40272(19) 0.32041(13) 0.54773(9) 0.0682(6) Uani 1 1 d G . .
C3 C 0.3930(2) 0.35199(14) 0.46581(9) 0.0726(7) Uani 1 1 d G . .
C4 C 0.4713(3) 0.28998(18) 0.41211(8) 0.0879(9) Uani 1 1 d G . .
H4 H 0.4648 0.3111 0.3573 0.105 Uiso 1 1 calc R . .
C5 C 0.5593(2) 0.19640(17) 0.44032(13) 0.0934(11) Uani 1 1 d G . .
H5 H 0.6116 0.1549 0.4044 0.112 Uiso 1 1 calc R . .
C6 C 0.5690(2) 0.16481(13) 0.52224(14) 0.0832(9) Uani 1 1 d GD . .
C7 C 0.4907(2) 0.22682(14) 0.57594(9) 0.0730(7) Uani 1 1 d GD . .
C8 C 0.6598(4) 0.0701(3) 0.5559(3) 0.1066(13) Uani 1 1 d D . .
H8 H 0.7144 0.0262 0.5224 0.128 Uiso 1 1 calc R . .
C9 C 0.6656(5) 0.0449(4) 0.6372(4) 0.1180(15) Uani 1 1 d D . .
H9 H 0.7255 -0.0160 0.6589 0.142 Uiso 1 1 calc R . .
C10 C 0.5835(5) 0.1086(3) 0.6882(3) 0.1054(12) Uani 1 1 d D . .
H10 H 0.5871 0.0899 0.7434 0.126 Uiso 1 1 calc R . .
C11 C 0.4976(4) 0.1987(3) 0.6570(2) 0.0822(8) Uani 1 1 d D . .
C12 C 0.4523(5) 0.3633(3) 0.72524(19) 0.0923(10) Uani 1 1 d U . .
C13 C 0.3205(6) 0.4253(4) 0.7566(3) 0.1257(15) Uani 1 1 d U . .
H13A H 0.3657 0.4885 0.7870 0.189 Uiso 1 1 calc R . .
H13B H 0.2681 0.3784 0.7918 0.189 Uiso 1 1 calc R . .
H13C H 0.2422 0.4492 0.7111 0.189 Uiso 1 1 calc R . .
C14 C 0.1360(2) 0.61542(14) 0.46908(11) 0.0722(7) Uani 1 1 d G . .
C15 C 0.0735(2) 0.67097(17) 0.53159(8) 0.0765(8) Uani 1 1 d G . .
C16 C -0.0163(2) 0.76721(17) 0.51414(12) 0.0833(9) Uani 1 1 d G . .
C17 C -0.0436(2) 0.80791(14) 0.43418(14) 0.0858(9) Uani 1 1 d G . .
C18 C 0.0190(3) 0.75236(17) 0.37168(10) 0.0853(9) Uani 1 1 d G . .
C19 C 0.1087(2) 0.65612(16) 0.38913(9) 0.0775(8) Uani 1 1 d G . .
H19 H 0.1506 0.6190 0.3473 0.093 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
F1 C15 1.311(2) . ?
F2 C16 1.331(3) . ?
F3 C17 1.339(3) . ?
F4 C18 1.311(2) . ?
O1 C12 1.350(4) . ?
O1 C11 1.399(4) . ?
O2 C12 1.192(4) . ?
C1 C2 1.323(4) . ?
C1 C3 1.434(3) . ?
C1 H1 0.9300 . ?
C2 C14 1.480(3) . ?
C2 H2 0.9300 . ?
N1 C3 1.3900 . ?
N1 C7 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 C8 1.438(4) . ?
C7 C11 1.367(3) . ?
C8 C9 1.365(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(5) . ?
C10 H10 0.9300 . ?
C12 C13 1.480(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?


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
C12 O1 C11 117.0(3) . . ?
C2 C1 C3 124.7(2) . . ?
C2 C1 H1 117.7 . . ?
C3 C1 H1 117.7 . . ?
C1 C2 C14 127.0(3) . . ?
C1 C2 H2 116.5 . . ?
C14 C2 H2 116.5 . . ?
C3 N1 C7 120.0 . . ?
N1 C3 C4 120.0 . . ?
N1 C3 C1 117.09(16) . . ?
C4 C3 C1 122.89(16) . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 C8 123.0(2) . . ?
C7 C6 C8 117.0(2) . . ?
C11 C7 C6 121.81(19) . . ?
C11 C7 N1 118.19(19) . . ?
C6 C7 N1 120.0 . . ?
C9 C8 C6 119.7(4) . . ?
C9 C8 H8 120.1 . . ?
C6 C8 H8 120.1 . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C7 120.7(3) . . ?
C10 C11 O1 120.6(3) . . ?
C7 C11 O1 118.5(3) . . ?
O2 C12 O1 123.2(4) . . ?
O2 C12 C13 126.4(4) . . ?
O1 C12 C13 110.3(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.0 . . ?
C15 C14 C2 117.82(16) . . ?
C19 C14 C2 122.18(16) . . ?
F1 C15 C14 122.47(17) . . ?
F1 C15 C16 117.52(17) . . ?
C14 C15 C16 120.0 . . ?
F2 C16 C17 119.69(18) . . ?
F2 C16 C15 120.31(18) . . ?
C17 C16 C15 120.0 . . ?
F3 C17 C16 119.11(18) . . ?
F3 C17 C18 120.88(18) . . ?
C16 C17 C18 120.0 . . ?
F4 C18 C19 121.64(18) . . ?
F4 C18 C17 118.36(18) . . ?
C19 C18 C17 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        67.05
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 937487'
