# Electronic Supplementary Material (ESI) for ChemComm.
# 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.
#
#  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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 F3 N2'
_chemical_formula_sum            'C15 H9 F3 N2'
_chemical_formula_weight         274.24

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   10.0878(8)
_cell_length_b                   29.196(2)
_cell_length_c                   9.8586(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.112(2)
_cell_angle_gamma                90.00
_cell_volume                     2536.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7034
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.95

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_T_max  0.9713
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18395
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4481
_reflns_number_gt                3632
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0840P)²+1.0656P] 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         4481
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.41980(18) 0.04759(5) 0.45277(17) 0.0749(5) Uani 1 1 d . . .
F2 F 0.30543(15) 0.08978(5) 0.53951(17) 0.0643(4) Uani 1 1 d . . .
F3 F 0.38755(18) 0.02413(5) 0.63922(19) 0.0827(5) Uani 1 1 d . . .
F4 F -0.0512(2) 0.07485(7) 0.47008(18) 0.0871(5) Uani 1 1 d . . .
F5 F -0.1534(2) 0.08582(8) 0.6074(3) 0.1102(8) Uani 1 1 d . . .
F6 F -0.0292(2) 0.02504(6) 0.6312(2) 0.1077(8) Uani 1 1 d . . .
N1 N 0.7373(2) 0.14542(6) 0.7980(2) 0.0483(4) Uani 1 1 d . . .
N2 N 0.6591(2) 0.05447(6) 0.8118(2) 0.0483(4) Uani 1 1 d . . .
N3 N 0.2889(2) 0.15401(6) 0.8054(2) 0.0458(4) Uani 1 1 d . . .
N4 N 0.2060(2) 0.06542(6) 0.8447(2) 0.0513(5) Uani 1 1 d . . .
C1 C 0.4842(3) 0.20321(7) 0.5918(3) 0.0517(5) Uani 1 1 d . . .
H1 H 0.5158 0.2111 0.6944 0.062 Uiso 1 1 calc R . .
C2 C 0.4042(3) 0.23440(8) 0.4749(3) 0.0603(6) Uani 1 1 d . . .
H2 H 0.3816 0.2631 0.4992 0.072 Uiso 1 1 calc R . .
C3 C 0.3580(3) 0.22342(9) 0.3238(3) 0.0615(7) Uani 1 1 d . . .
H3 H 0.3028 0.2444 0.2452 0.074 Uiso 1 1 calc R . .
C4 C 0.3933(3) 0.18146(9) 0.2886(3) 0.0625(7) Uani 1 1 d . . .
H4 H 0.3632 0.1742 0.1858 0.075 Uiso 1 1 calc R . .
C5 C 0.4733(3) 0.14957(8) 0.4043(3) 0.0551(6) Uani 1 1 d . . .
H5 H 0.4970 0.1211 0.3791 0.066 Uiso 1 1 calc R . .
C6 C 0.5178(2) 0.16020(7) 0.5572(2) 0.0418(5) Uani 1 1 d . . .
C7 C 0.6102(2) 0.12835(7) 0.6873(2) 0.0412(5) Uani 1 1 d . . .
C8 C 0.5708(2) 0.08194(7) 0.6986(2) 0.0424(5) Uani 1 1 d . . .
C9 C 0.4212(3) 0.06056(7) 0.5834(3) 0.0502(5) Uani 1 1 d . . .
C10 C 0.7934(3) 0.07162(8) 0.9228(3) 0.0499(5) Uani 1 1 d . . .
C11 C 0.8315(3) 0.11780(8) 0.9169(3) 0.0501(5) Uani 1 1 d . . .
C12 C 0.9703(3) 0.13491(10) 1.0355(3) 0.0736(8) Uani 1 1 d . . .
H12 H 0.9968 0.1653 1.0336 0.088 Uiso 1 1 calc R . .
C13 C 1.0649(3) 0.10704(12) 1.1520(3) 0.0886(10) Uani 1 1 d . . .
H13 H 1.1564 0.1185 1.2298 0.106 Uiso 1 1 calc R . .
C14 C 1.0275(3) 0.06122(11) 1.1576(4) 0.0865(10) Uani 1 1 d . . .
H14 H 1.0947 0.0426 1.2386 0.104 Uiso 1 1 calc R . .
C15 C 0.8946(3) 0.04355(9) 1.0463(3) 0.0685(7) Uani 1 1 d . . .
H15 H 0.8702 0.0131 1.0514 0.082 Uiso 1 1 calc R . .
C16 C -0.0863(3) 0.18536(8) 0.5841(3) 0.0583(6) Uani 1 1 d . . .
H16 H -0.1133 0.1746 0.6561 0.070 Uiso 1 1 calc R . .
C17 C -0.1780(3) 0.21673(9) 0.4726(3) 0.0672(7) Uani 1 1 d . . .
H17 H -0.2660 0.2271 0.4707 0.081 Uiso 1 1 calc R . .
C18 C -0.1404(3) 0.23259(9) 0.3652(3) 0.0666(7) Uani 1 1 d . . .
H18 H -0.2026 0.2535 0.2899 0.080 Uiso 1 1 calc R . .
C19 C -0.0093(3) 0.21722(11) 0.3698(4) 0.0770(8) Uani 1 1 d . . .
H19 H 0.0169 0.2278 0.2969 0.092 Uiso 1 1 calc R . .
C20 C 0.0831(3) 0.18641(9) 0.4810(3) 0.0628(7) Uani 1 1 d . . .
H20 H 0.1721 0.1766 0.4837 0.075 Uiso 1 1 calc R . .
C21 C 0.0453(2) 0.16992(7) 0.5888(2) 0.0436(5) Uani 1 1 d . . .
C22 C 0.1515(2) 0.13818(7) 0.7120(2) 0.0423(5) Uani 1 1 d . . .
C23 C 0.1142(3) 0.09198(7) 0.7309(2) 0.0451(5) Uani 1 1 d . . .
C24 C -0.0305(3) 0.06928(8) 0.6127(3) 0.0522(6) Uani 1 1 d . . .
C25 C 0.3454(3) 0.08244(7) 0.9453(3) 0.0487(5) Uani 1 1 d . . .
C26 C 0.3888(2) 0.12635(7) 0.9216(2) 0.0455(5) Uani 1 1 d . . .
C27 C 0.5381(3) 0.14165(8) 1.0208(3) 0.0531(6) Uani 1 1 d . . .
H27 H 0.5691 0.1702 1.0049 0.064 Uiso 1 1 calc R . .
C28 C 0.6366(3) 0.11465(9) 1.1397(3) 0.0619(6) Uani 1 1 d . . .
H28 H 0.7344 0.1251 1.2056 0.074 Uiso 1 1 calc R . .
C29 C 0.5920(3) 0.07115(10) 1.1639(3) 0.0679(7) Uani 1 1 d . . .
H29 H 0.6609 0.0531 1.2456 0.081 Uiso 1 1 calc R . .
C30 C 0.4501(3) 0.05526(9) 1.0700(3) 0.0634(7) Uani 1 1 d . . .
H30 H 0.4217 0.0265 1.0876 0.076 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 C9 1.335(3) . ?
F2 C9 1.337(3) . ?
F3 C9 1.316(3) . ?
F4 C24 1.327(3) . ?
F5 C24 1.308(3) . ?
F6 C24 1.303(3) . ?
N1 C7 1.312(3) . ?
N1 C11 1.358(3) . ?
N2 C8 1.310(3) . ?
N2 C10 1.357(3) . ?
N3 C22 1.319(3) . ?
N3 C26 1.363(3) . ?
N4 C23 1.306(3) . ?
N4 C25 1.360(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.488(3) . ?
C7 C8 1.432(3) . ?
C8 C9 1.513(3) . ?
C10 C15 1.410(3) . ?
C10 C11 1.411(3) . ?
C11 C12 1.409(3) . ?
C12 C13 1.351(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.381(3) . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.489(3) . ?
C22 C23 1.436(3) . ?
C23 C24 1.508(3) . ?
C25 C26 1.411(3) . ?
C25 C30 1.412(3) . ?
C26 C27 1.411(3) . ?
C27 C28 1.360(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.406(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.353(4) . ?
C29 H29 0.9300 . ?
C30 H30 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
C7 N1 C11 118.86(18) . . ?
C8 N2 C10 117.34(18) . . ?
C22 N3 C26 118.38(18) . . ?
C23 N4 C25 117.29(18) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 122.30(19) . . ?
C1 C6 C7 118.67(19) . . ?
N1 C7 C8 119.38(18) . . ?
N1 C7 C6 115.35(18) . . ?
C8 C7 C6 125.27(18) . . ?
N2 C8 C7 123.14(19) . . ?
N2 C8 C9 113.79(18) . . ?
C7 C8 C9 123.05(18) . . ?
F3 C9 F1 106.87(19) . . ?
F3 C9 F2 106.7(2) . . ?
F1 C9 F2 105.72(18) . . ?
F3 C9 C8 112.69(18) . . ?
F1 C9 C8 112.3(2) . . ?
F2 C9 C8 112.02(18) . . ?
N2 C10 C15 120.1(2) . . ?
N2 C10 C11 120.32(19) . . ?
C15 C10 C11 119.6(2) . . ?
N1 C11 C12 120.1(2) . . ?
N1 C11 C10 120.9(2) . . ?
C12 C11 C10 119.0(2) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C21 C16 C17 120.2(2) . . ?
C21 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 118.8(2) . . ?
C20 C21 C22 119.1(2) . . ?
C16 C21 C22 121.9(2) . . ?
N3 C22 C23 119.41(19) . . ?
N3 C22 C21 116.50(18) . . ?
C23 C22 C21 124.07(19) . . ?
N4 C23 C22 123.2(2) . . ?
N4 C23 C24 114.69(18) . . ?
C22 C23 C24 121.95(19) . . ?
F6 C24 F5 108.5(2) . . ?
F6 C24 F4 104.8(2) . . ?
F5 C24 F4 104.8(2) . . ?
F6 C24 C23 112.78(19) . . ?
F5 C24 C23 114.3(2) . . ?
F4 C24 C23 111.0(2) . . ?
N4 C25 C26 120.36(19) . . ?
N4 C25 C30 120.0(2) . . ?
C26 C25 C30 119.6(2) . . ?
N3 C26 C25 121.03(19) . . ?
N3 C26 C27 119.91(19) . . ?
C25 C26 C27 119.1(2) . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.7(2) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 120.9(2) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C25 119.8(2) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?

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
C6 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 -177.0(2) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
C2 C1 C6 C7 177.4(2) . . . . ?
C11 N1 C7 C8 3.0(3) . . . . ?
C11 N1 C7 C6 -176.77(19) . . . . ?
C5 C6 C7 N1 124.3(2) . . . . ?
C1 C6 C7 N1 -51.2(3) . . . . ?
C5 C6 C7 C8 -55.5(3) . . . . ?
C1 C6 C7 C8 129.0(2) . . . . ?
C10 N2 C8 C7 0.4(3) . . . . ?
C10 N2 C8 C9 -177.9(2) . . . . ?
N1 C7 C8 N2 -3.1(3) . . . . ?
C6 C7 C8 N2 176.7(2) . . . . ?
N1 C7 C8 C9 175.0(2) . . . . ?
C6 C7 C8 C9 -5.2(3) . . . . ?
N2 C8 C9 F3 18.6(3) . . . . ?
C7 C8 C9 F3 -159.7(2) . . . . ?
N2 C8 C9 F1 -102.2(2) . . . . ?
C7 C8 C9 F1 79.5(3) . . . . ?
N2 C8 C9 F2 139.0(2) . . . . ?
C7 C8 C9 F2 -39.3(3) . . . . ?
C8 N2 C10 C15 -179.0(2) . . . . ?
C8 N2 C10 C11 2.2(3) . . . . ?
C7 N1 C11 C12 178.6(2) . . . . ?
C7 N1 C11 C10 -0.5(3) . . . . ?
N2 C10 C11 N1 -2.2(4) . . . . ?
C15 C10 C11 N1 178.9(2) . . . . ?
N2 C10 C11 C12 178.7(2) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?
N1 C11 C12 C13 -178.7(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
N2 C10 C15 C14 -179.1(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C21 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 C21 0.8(5) . . . . ?
C19 C20 C21 C16 -0.8(4) . . . . ?
C19 C20 C21 C22 -177.3(3) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C17 C16 C21 C22 176.6(2) . . . . ?
C26 N3 C22 C23 -3.0(3) . . . . ?
C26 N3 C22 C21 178.81(18) . . . . ?
C20 C21 C22 N3 59.9(3) . . . . ?
C16 C21 C22 N3 -116.5(2) . . . . ?
C20 C21 C22 C23 -118.3(3) . . . . ?
C16 C21 C22 C23 65.3(3) . . . . ?
C25 N4 C23 C22 -2.7(3) . . . . ?
C25 N4 C23 C24 172.9(2) . . . . ?
N3 C22 C23 N4 5.7(3) . . . . ?
C21 C22 C23 N4 -176.2(2) . . . . ?
N3 C22 C23 C24 -169.6(2) . . . . ?
C21 C22 C23 C24 8.5(3) . . . . ?
N4 C23 C24 F6 -10.0(3) . . . . ?
C22 C23 C24 F6 165.7(2) . . . . ?
N4 C23 C24 F5 114.5(3) . . . . ?
C22 C23 C24 F5 -69.8(3) . . . . ?
N4 C23 C24 F4 -127.3(2) . . . . ?
C22 C23 C24 F4 48.4(3) . . . . ?
C23 N4 C25 C26 -2.5(3) . . . . ?
C23 N4 C25 C30 -179.5(2) . . . . ?
C22 N3 C26 C25 -2.1(3) . . . . ?
C22 N3 C26 C27 178.1(2) . . . . ?
N4 C25 C26 N3 5.1(3) . . . . ?
C30 C25 C26 N3 -177.9(2) . . . . ?
N4 C25 C26 C27 -175.1(2) . . . . ?
C30 C25 C26 C27 1.9(3) . . . . ?
N3 C26 C27 C28 178.0(2) . . . . ?
C25 C26 C27 C28 -1.7(3) . . . . ?
C26 C27 C28 C29 0.9(4) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C28 C29 C30 C25 0.4(4) . . . . ?
N4 C25 C30 C29 175.8(3) . . . . ?
C26 C25 C30 C29 -1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 1023298'
#######################################################################
#
#                 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_mo_20140428a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 F3 N2 O'
_chemical_formula_sum            'C15 H9 F3 N2 O'
_chemical_formula_weight         290.24

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           Tetragonal
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   20.088(4)
_cell_length_b                   20.088(4)
_cell_length_c                   13.191(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5322.7(18)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3832
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      25.23

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2368
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10557
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2614
_reflns_number_gt                1971
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'

_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)+(0.1386P)²+0.4235P] 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         2614
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.2005
_refine_ls_wR_factor_gt          0.1742
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.35549(11) 0.73411(9) -0.07920(15) 0.1158(7) Uani 1 1 d . . .
F2 F 0.32295(11) 0.75123(8) 0.07082(16) 0.1138(7) Uani 1 1 d . . .
F3 F 0.41589(10) 0.70443(9) 0.0441(2) 0.1392(9) Uani 1 1 d . . .
N1 N 0.22326(8) 0.57361(8) 0.02178(10) 0.0453(4) Uani 1 1 d . . .
N2 N 0.36187(9) 0.58978(8) 0.02458(12) 0.0549(5) Uani 1 1 d . . .
O1 O 0.16039(7) 0.56518(7) 0.02285(11) 0.0608(4) Uani 1 1 d . . .
C1 C 0.26482(10) 0.51804(8) 0.03151(11) 0.0440(5) Uani 1 1 d . . .
C2 C 0.23724(11) 0.45430(9) 0.03983(13) 0.0520(5) Uani 1 1 d . . .
H2 H 0.1913 0.4484 0.0416 0.062 Uiso 1 1 calc R . .
C3 C 0.27902(13) 0.40110(10) 0.04533(15) 0.0627(6) Uani 1 1 d . . .
H3 H 0.2613 0.3584 0.0503 0.075 Uiso 1 1 calc R . .
C4 C 0.34768(14) 0.40943(11) 0.04361(17) 0.0680(6) Uani 1 1 d . . .
H4 H 0.3752 0.3723 0.0471 0.082 Uiso 1 1 calc R . .
C5 C 0.37539(12) 0.47163(11) 0.03682(15) 0.0612(6) Uani 1 1 d . . .
H5 H 0.4214 0.4766 0.0365 0.073 Uiso 1 1 calc R . .
C6 C 0.33411(10) 0.52786(9) 0.03029(12) 0.0480(5) Uani 1 1 d . . .
C7 C 0.32062(11) 0.63966(10) 0.01467(14) 0.0544(5) Uani 1 1 d . . .
C8 C 0.25068(10) 0.63503(9) 0.00807(13) 0.0489(5) Uani 1 1 d . . .
C9 C 0.20463(11) 0.69024(10) -0.01672(17) 0.0593(6) Uani 1 1 d . . .
C10 C 0.20677(13) 0.71683(12) -0.11444(19) 0.0732(7) Uani 1 1 d . . .
H10 H 0.2368 0.7002 -0.1618 0.088 Uiso 1 1 calc R . .
C11 C 0.16435(17) 0.76756(15) -0.1403(3) 0.0969(10) Uani 1 1 d . . .
H11 H 0.1661 0.7856 -0.2052 0.116 Uiso 1 1 calc R . .
C12 C 0.12049(19) 0.79123(14) -0.0731(4) 0.1084(13) Uani 1 1 d . . .
H12 H 0.0923 0.8259 -0.0919 0.130 Uiso 1 1 calc R . .
C13 C 0.11626(16) 0.76516(17) 0.0237(3) 0.1073(12) Uani 1 1 d . . .
H13 H 0.0849 0.7816 0.0691 0.129 Uiso 1 1 calc R . .
C14 C 0.15957(14) 0.71383(13) 0.0532(2) 0.0793(7) Uani 1 1 d . . .
H14 H 0.1578 0.6962 0.1183 0.095 Uiso 1 1 calc R . .
C15 C 0.35413(14) 0.70748(12) 0.0131(2) 0.0762(7) 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
F1 C15 1.330(3) . ?
F2 C15 1.321(3) . ?
F3 C15 1.308(3) . ?
N1 O1 1.274(2) . ?
N1 C8 1.363(2) . ?
N1 C1 1.400(2) . ?
N2 C7 1.307(3) . ?
N2 C6 1.365(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.361(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.411(3) . ?
C7 C15 1.520(3) . ?
C8 C9 1.481(3) . ?
C9 C14 1.376(4) . ?
C9 C10 1.396(3) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.337(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.404(4) . ?
C13 H13 0.9300 . ?
C14 H14 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
O1 N1 C8 121.48(15) . . ?
O1 N1 C1 118.95(15) . . ?
C8 N1 C1 119.53(16) . . ?
C7 N2 C6 116.43(18) . . ?
C2 C1 N1 120.04(18) . . ?
C2 C1 C6 121.42(17) . . ?
N1 C1 C6 118.52(16) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N2 C6 C5 119.7(2) . . ?
N2 C6 C1 122.20(18) . . ?
C5 C6 C1 118.11(18) . . ?
N2 C7 C8 125.96(18) . . ?
N2 C7 C15 114.1(2) . . ?
C8 C7 C15 119.96(19) . . ?
N1 C8 C7 116.99(16) . . ?
N1 C8 C9 117.05(17) . . ?
C7 C8 C9 125.90(17) . . ?
C14 C9 C10 120.5(2) . . ?
C14 C9 C8 121.4(2) . . ?
C10 C9 C8 118.1(2) . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 118.4(3) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
F3 C15 F2 107.5(2) . . ?
F3 C15 F1 106.6(2) . . ?
F2 C15 F1 105.7(2) . . ?
F3 C15 C7 111.9(2) . . ?
F2 C15 C7 112.2(2) . . ?
F1 C15 C7 112.5(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
O1 N1 C1 C2 1.5(2) . . . . ?
C8 N1 C1 C2 -176.37(14) . . . . ?
O1 N1 C1 C6 -179.97(14) . . . . ?
C8 N1 C1 C6 2.2(2) . . . . ?
N1 C1 C2 C3 177.55(15) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C7 N2 C6 C5 177.41(17) . . . . ?
C7 N2 C6 C1 -3.6(2) . . . . ?
C4 C5 C6 N2 179.34(18) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 N2 -178.45(14) . . . . ?
N1 C1 C6 N2 3.0(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
N1 C1 C6 C5 -177.99(14) . . . . ?
C6 N2 C7 C8 -0.9(3) . . . . ?
C6 N2 C7 C15 177.62(17) . . . . ?
O1 N1 C8 C7 176.01(15) . . . . ?
C1 N1 C8 C7 -6.2(2) . . . . ?
O1 N1 C8 C9 -6.5(2) . . . . ?
C1 N1 C8 C9 171.27(15) . . . . ?
N2 C7 C8 N1 5.9(3) . . . . ?
C15 C7 C8 N1 -172.56(18) . . . . ?
N2 C7 C8 C9 -171.32(19) . . . . ?
C15 C7 C8 C9 10.2(3) . . . . ?
N1 C8 C9 C14 68.4(3) . . . . ?
C7 C8 C9 C14 -114.4(3) . . . . ?
N1 C8 C9 C10 -109.9(2) . . . . ?
C7 C8 C9 C10 67.3(3) . . . . ?
C14 C9 C10 C11 1.1(3) . . . . ?
C8 C9 C10 C11 179.3(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C8 C9 C14 C13 -178.4(2) . . . . ?
C12 C13 C14 C9 -1.0(4) . . . . ?
N2 C7 C15 F3 -14.2(3) . . . . ?
C8 C7 C15 F3 164.5(2) . . . . ?
N2 C7 C15 F2 -135.1(2) . . . . ?
C8 C7 C15 F2 43.5(3) . . . . ?
N2 C7 C15 F1 105.9(2) . . . . ?
C8 C7 C15 F1 -75.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.106
_database_code_depnum_ccdc_archive 'CCDC 1023299'
