# Electronic Supplementary Material (ESI) for ChemComm.
# 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.
# 
#  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_g140610b
_audit_creation_date             2014-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 F N O3'
_chemical_formula_sum            'C18 H16 F N O3'
_chemical_formula_weight         313.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOPd
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.2895(6)
_cell_length_b                   10.3789(5)
_cell_length_c                   13.6515(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.765(6)
_cell_angle_gamma                90.00
_cell_volume                     1474.98(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5237
_cell_measurement_temperature    294.1(2)
_cell_measurement_theta_max      30.1360
_cell_measurement_theta_min      3.5760
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12936
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.80
_diffrn_ambient_temperature      294.1(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   39.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514  178.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   24.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -99.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -61.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889 -178.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -79.00  -48.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -57.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega  -85.00   25.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -19.0000 -120.0000 110

#__ type_ start__ end____ width___ exp.time_
  6 omega  -41.00   -4.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   37.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00   60.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   49.0000  -30.0000 103
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0466894000
_diffrn_orient_matrix_UB_12      0.0101821000
_diffrn_orient_matrix_UB_13      0.0221129000
_diffrn_orient_matrix_UB_21      0.0433892000
_diffrn_orient_matrix_UB_22      0.0407987000
_diffrn_orient_matrix_UB_23      0.0392048000
_diffrn_orient_matrix_UB_31      -0.0240692000
_diffrn_orient_matrix_UB_32      0.0538921000
_diffrn_orient_matrix_UB_33      -0.0338679000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2392
_reflns_number_total             3005
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0871P)²+0.8771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1904
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.10928(18) 0.91186(17) 0.15122(19) 0.0828(7) Uani 1 d . . .
O1 O -0.36385(15) 0.87905(18) 0.02019(16) 0.0513(5) Uani 1 d . . .
O2 O 0.34900(16) 0.76334(17) 0.16500(15) 0.0474(5) Uani 1 d . . .
O3 O 0.34277(17) 0.7834(2) 0.32713(16) 0.0553(5) Uani 1 d . . .
N1 N 0.14100(17) 0.58129(17) 0.17378(14) 0.0332(4) Uani 1 d . . .
H1 H 0.2231 0.5901 0.2020 0.040 Uiso 1 calc . . R
C1 C 0.0879(2) 0.4609(2) 0.15468(17) 0.0325(5) Uani 1 d . . .
C2 C 0.1715(2) 0.3537(2) 0.17947(19) 0.0391(5) Uani 1 d . . .
H2 H 0.2599 0.3668 0.2086 0.047 Uiso 1 calc . . R
C3 C 0.1245(2) 0.2322(2) 0.1614(2) 0.0434(6) Uani 1 d . . .
H3 H 0.1804 0.1623 0.1776 0.052 Uiso 1 calc . . R
C4 C -0.0086(3) 0.2119(2) 0.1180(2) 0.0451(6) Uani 1 d . . .
H4 H -0.0405 0.1283 0.1062 0.054 Uiso 1 calc . . R
C5 C -0.0922(2) 0.3139(2) 0.0929(2) 0.0416(6) Uani 1 d . . .
H5 H -0.1802 0.2984 0.0636 0.050 Uiso 1 calc . . R
C6 C -0.0468(2) 0.4420(2) 0.11070(17) 0.0326(5) Uani 1 d . . .
C7 C -0.12791(19) 0.5549(2) 0.08683(16) 0.0324(5) Uani 1 d . . .
C8 C -0.2637(2) 0.5472(2) 0.0453(2) 0.0404(6) Uani 1 d . . .
H8 H -0.3034 0.4670 0.0325 0.048 Uiso 1 calc . . R
C9 C -0.3370(2) 0.6561(3) 0.0239(2) 0.0438(6) Uani 1 d . . .
H9 H -0.4260 0.6493 -0.0034 0.053 Uiso 1 calc . . R
C10 C -0.2794(2) 0.7780(2) 0.04271(18) 0.0372(5) Uani 1 d . . .
C11 C -0.1477(2) 0.7898(2) 0.08207(17) 0.0345(5) Uani 1 d . . .
H11 H -0.1098 0.8710 0.0936 0.041 Uiso 1 calc . . R
C12 C -0.07108(19) 0.6788(2) 0.10471(16) 0.0307(5) Uani 1 d . . .
C13 C 0.0675(2) 0.6826(2) 0.14931(17) 0.0318(5) Uani 1 d . . .
C14 C 0.1460(2) 0.8025(2) 0.1724(2) 0.0383(5) Uani 1 d . . .
C15 C 0.2911(2) 0.7791(2) 0.2323(2) 0.0397(6) Uani 1 d . . .
C16 C 0.4865(2) 0.7343(3) 0.2125(3) 0.0587(8) Uani 1 d . . .
H16A H 0.5259 0.7813 0.2787 0.070 Uiso 1 calc . . R
H16B H 0.5269 0.7617 0.1649 0.070 Uiso 1 calc . . R
C17 C 0.5070(3) 0.5939(3) 0.2331(3) 0.0732(10) Uani 1 d . . .
H17A H 0.4642 0.5474 0.1682 0.110 Uiso 1 calc . . GR
H17B H 0.4727 0.5682 0.2844 0.110 Uiso 1 calc . . GR
H17C H 0.5973 0.5754 0.2600 0.110 Uiso 1 calc . . GR
C18 C -0.3126(3) 1.0059(3) 0.0355(3) 0.0570(7) Uani 1 d . . .
H18A H -0.2661 1.0194 -0.0095 0.086 Uiso 1 calc . . GR
H18B H -0.2558 1.0169 0.1084 0.086 Uiso 1 calc . . GR
H18C H -0.3815 1.0672 0.0178 0.086 Uiso 1 calc . . GR


_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 C14 1.205(3) . ?
O1 C10 1.370(3) . ?
O1 C18 1.421(3) . ?
O2 C15 1.327(3) . ?
O2 C16 1.463(3) . ?
O3 C15 1.198(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.367(3) . ?
N1 C13 1.301(3) . ?
C1 C2 1.412(3) . ?
C1 C6 1.416(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.354(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.412(3) . ?
C6 C7 1.445(3) . ?
C7 C8 1.416(3) . ?
C7 C12 1.416(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.363(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.401(3) . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(3) . ?
C12 C13 1.443(3) . ?
C13 C14 1.488(3) . ?
C14 C15 1.541(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.485(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C10 O1 C18 117.91(18) . . ?
C15 O2 C16 116.1(2) . . ?
C1 N1 H1 119.9 . . ?
C13 N1 H1 119.9 . . ?
C13 N1 C1 120.11(18) . . ?
N1 C1 C2 118.14(19) . . ?
N1 C1 C6 121.81(19) . . ?
C2 C1 C6 120.1(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 117.79(19) . . ?
C5 C6 C7 124.7(2) . . ?
C8 C7 C6 122.6(2) . . ?
C12 C7 C6 119.52(18) . . ?
C12 C7 C8 117.9(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
O1 C10 C9 114.64(19) . . ?
O1 C10 C11 124.9(2) . . ?
C11 C10 C9 120.4(2) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C13 116.29(18) . . ?
C11 C12 C7 120.58(19) . . ?
C11 C12 C13 123.12(19) . . ?
N1 C13 C12 124.45(19) . . ?
N1 C13 C14 110.66(18) . . ?
C12 C13 C14 124.89(19) . . ?
F1 C14 C13 127.9(2) . . ?
F1 C14 C15 118.2(2) . . ?
C13 C14 C15 113.88(18) . . ?
O2 C15 C14 111.1(2) . . ?
O3 C15 O2 126.1(2) . . ?
O3 C15 C14 122.7(2) . . ?
O2 C16 H16A 109.6 . . ?
O2 C16 H16B 109.6 . . ?
O2 C16 C17 110.3(2) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
F1 C14 C15 O2 -89.7(3) . . . . ?
F1 C14 C15 O3 85.9(3) . . . . ?
O1 C10 C11 C12 178.3(2) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
N1 C1 C6 C5 179.3(2) . . . . ?
N1 C1 C6 C7 -0.4(3) . . . . ?
N1 C13 C14 F1 173.2(3) . . . . ?
N1 C13 C14 C15 -7.7(3) . . . . ?
C1 N1 C13 C12 2.0(3) . . . . ?
C1 N1 C13 C14 -177.36(19) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C6 C7 C8 -178.3(2) . . . . ?
C1 C6 C7 C12 2.0(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 179.99(19) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -179.9(2) . . . . ?
C5 C6 C7 C8 2.0(4) . . . . ?
C5 C6 C7 C12 -177.7(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C7 C8 C9 179.9(2) . . . . ?
C6 C7 C12 C11 179.93(19) . . . . ?
C6 C7 C12 C13 -1.6(3) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C7 C12 C13 N1 -0.4(3) . . . . ?
C7 C12 C13 C14 178.9(2) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C7 C12 C13 178.65(19) . . . . ?
C8 C9 C10 O1 -178.5(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C10 C11 C12 C13 -177.9(2) . . . . ?
C11 C12 C13 N1 178.0(2) . . . . ?
C11 C12 C13 C14 -2.7(3) . . . . ?
C12 C7 C8 C9 -0.4(4) . . . . ?
C12 C13 C14 F1 -6.1(4) . . . . ?
C12 C13 C14 C15 173.0(2) . . . . ?
C13 N1 C1 C2 178.1(2) . . . . ?
C13 N1 C1 C6 -1.6(3) . . . . ?
C13 C14 C15 O2 91.1(2) . . . . ?
C13 C14 C15 O3 -93.2(3) . . . . ?
C15 O2 C16 C17 84.5(3) . . . . ?
C16 O2 C15 O3 7.3(4) . . . . ?
C16 O2 C15 C14 -177.2(2) . . . . ?
C18 O1 C10 C9 -178.9(2) . . . . ?
C18 O1 C10 C11 2.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1009377'
