# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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.
#
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#  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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_130524c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 F N O2'
_chemical_formula_sum            'C17 H12 F N O2'
_chemical_formula_weight         281.28

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.395(4)
_cell_length_b                   7.210(2)
_cell_length_c                   17.653(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.390(18)
_cell_angle_gamma                90.00
_cell_volume                     1359.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.01

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_T_max  0.9862
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7212
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2394
_reflns_number_gt                1470
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1359P)²+0.4481P] 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         2394
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2428
_refine_ls_wR_factor_gt          0.2064
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.7736(4) 0.4091(6) 0.2929(2) 0.0892(12) Uani 1 1 d . . .
H1A H 0.7981 0.4489 0.3481 0.134 Uiso 1 1 calc R . .
H1B H 0.8465 0.3978 0.2778 0.134 Uiso 1 1 calc R . .
H1C H 0.7323 0.2912 0.2869 0.134 Uiso 1 1 calc R . .
C2 C 0.6863(3) 0.5485(5) 0.23958(19) 0.0622(8) Uani 1 1 d . . .
C3 C 0.6190(3) 0.5128(5) 0.1589(2) 0.0719(9) Uani 1 1 d . . .
H3 H 0.6273 0.3986 0.1368 0.086 Uiso 1 1 calc R . .
C4 C 0.5395(3) 0.6457(6) 0.1109(2) 0.0718(9) Uani 1 1 d . . .
H4 H 0.4955 0.6189 0.0569 0.086 Uiso 1 1 calc R . .
C5 C 0.5239(3) 0.8157(5) 0.14109(19) 0.061 Uani 1 1 d . . .
C6 C 0.5911(3) 0.8500(5) 0.2212(2) 0.0636(8) Uani 1 1 d . . .
H6 H 0.5830 0.9642 0.2434 0.076 Uiso 1 1 calc R . .
C7 C 0.6694(3) 0.7199(5) 0.26870(19) 0.0624(8) Uani 1 1 d . . .
H7 H 0.7129 0.7478 0.3227 0.075 Uiso 1 1 calc R . .
C8 C 0.4367(3) 0.9613(5) 0.0935(2) 0.073 Uani 1 1 d . . .
H8 H 0.4337 1.0710 0.1205 0.087 Uiso 1 1 calc R . .
C9 C 0.3645(3) 0.9513(6) 0.0186(2) 0.078 Uani 1 1 d . . .
H9 H 0.3669 0.8428 -0.0094 0.093 Uiso 1 1 calc R . .
C10 C 0.2806(3) 1.0958(4) -0.02468(19) 0.058 Uani 1 1 d . . .
C11 C 0.2062(3) 1.0563(5) -0.1101(2) 0.0646(9) Uani 1 1 d . . .
C12 C 0.1082(3) 1.3452(4) -0.11400(18) 0.0548(8) Uani 1 1 d . . .
C13 C 0.1826(3) 1.3785(4) -0.03419(16) 0.0504(7) Uani 1 1 d . . .
C14 C 0.1674(3) 1.5447(5) 0.0007(2) 0.0633(8) Uani 1 1 d . . .
H14 H 0.2156 1.5719 0.0539 0.076 Uiso 1 1 calc R . .
C15 C 0.0809(3) 1.6665(5) -0.0444(3) 0.0724(10) Uani 1 1 d . . .
C16 C 0.0078(3) 1.6325(6) -0.1237(3) 0.0801(11) Uani 1 1 d . . .
H16 H -0.0500 1.7205 -0.1528 0.096 Uiso 1 1 calc R . .
C17 C 0.0206(3) 1.4702(5) -0.1591(2) 0.0717(10) Uani 1 1 d . . .
H17 H -0.0285 1.4444 -0.2123 0.086 Uiso 1 1 calc R . .
F1 F 0.0673(2) 1.8293(3) -0.01052(18) 0.1084(8) Uani 1 1 d . . .
N1 N 0.2697(2) 1.2497(4) 0.01105(14) 0.0591(7) Uani 1 1 d . . .
O1 O 0.2142(3) 0.9160(4) -0.14581(16) 0.0879(8) Uani 1 1 d . . .
O2 O 0.1203(2) 1.1831(3) -0.15090(13) 0.0677(6) 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 C2 1.494(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.378(5) . ?
C2 C3 1.386(5) . ?
C3 C4 1.387(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 C8 1.488(5) . ?
C6 C7 1.363(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.294(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.440(5) . ?
C9 H9 0.9300 . ?
C10 N1 1.303(4) . ?
C10 C11 1.478(5) . ?
C11 O1 1.212(4) . ?
C11 O2 1.349(4) . ?
C12 O2 1.368(4) . ?
C12 C17 1.374(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.385(4) . ?
C13 N1 1.390(4) . ?
C14 C15 1.352(5) . ?
C14 H14 0.9300 . ?
C15 F1 1.351(4) . ?
C15 C16 1.378(5) . ?
C16 C17 1.359(5) . ?
C16 H16 0.9300 . ?
C17 H17 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 116.8(3) . . ?
C7 C2 C1 121.2(3) . . ?
C3 C2 C1 122.1(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.3(3) . . ?
C4 C5 C8 124.3(3) . . ?
C6 C5 C8 118.4(3) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 122.3(3) . . ?
C6 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
C9 C8 C5 126.8(4) . . ?
C9 C8 H8 116.6 . . ?
C5 C8 H8 116.6 . . ?
C8 C9 C10 124.7(4) . . ?
C8 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
N1 C10 C9 121.1(3) . . ?
N1 C10 C11 122.7(3) . . ?
C9 C10 C11 116.1(3) . . ?
O1 C11 O2 117.4(3) . . ?
O1 C11 C10 124.8(3) . . ?
O2 C11 C10 117.7(3) . . ?
O2 C12 C17 117.2(3) . . ?
O2 C12 C13 120.2(3) . . ?
C17 C12 C13 122.5(3) . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 N1 119.8(3) . . ?
C12 C13 N1 121.9(3) . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F1 C15 C14 118.5(3) . . ?
F1 C15 C16 118.8(4) . . ?
C14 C15 C16 122.7(4) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 118.1(3) . . ?
C16 C17 H17 121.0 . . ?
C12 C17 H17 121.0 . . ?
C10 N1 C13 117.4(3) . . ?
C11 O2 C12 120.0(2) . . ?

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
C7 C2 C3 C4 0.3(5) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C5 C8 -177.7(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C8 C5 C6 C7 177.8(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C3 C2 C7 C6 -0.4(5) . . . . ?
C1 C2 C7 C6 179.4(3) . . . . ?
C4 C5 C8 C9 -0.3(6) . . . . ?
C6 C5 C8 C9 -178.3(3) . . . . ?
C5 C8 C9 C10 179.4(3) . . . . ?
C8 C9 C10 N1 -1.8(5) . . . . ?
C8 C9 C10 C11 180.0(3) . . . . ?
N1 C10 C11 O1 179.3(3) . . . . ?
C9 C10 C11 O1 -2.5(5) . . . . ?
N1 C10 C11 O2 -2.8(4) . . . . ?
C9 C10 C11 O2 175.4(3) . . . . ?
O2 C12 C13 C14 179.9(2) . . . . ?
C17 C12 C13 C14 -0.2(4) . . . . ?
O2 C12 C13 N1 -0.8(4) . . . . ?
C17 C12 C13 N1 179.1(3) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
N1 C13 C14 C15 -179.2(3) . . . . ?
C13 C14 C15 F1 -179.3(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
F1 C15 C16 C17 179.6(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C12 -0.7(5) . . . . ?
O2 C12 C17 C16 -179.6(3) . . . . ?
C13 C12 C17 C16 0.5(5) . . . . ?
C9 C10 N1 C13 -177.2(3) . . . . ?
C11 C10 N1 C13 0.9(4) . . . . ?
C14 C13 N1 C10 -179.8(3) . . . . ?
C12 C13 N1 C10 0.9(4) . . . . ?
O1 C11 O2 C12 -179.2(3) . . . . ?
C10 C11 O2 C12 2.8(4) . . . . ?
C17 C12 O2 C11 178.9(3) . . . . ?
C13 C12 O2 C11 -1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 944907'
