# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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 
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#  except for the purpose of generating routine backup copies 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 912043'
#TrackingRef 'web_deposit_cif_file_0_MaoLiu_1353568851.a.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl F3 N2'
_chemical_formula_sum            'C18 H14 Cl F3 N2'
_chemical_formula_weight         350.76
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'
F F 0.0171 0.0103 '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'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
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                   14.103(3)
_cell_length_b                   7.6310(15)
_cell_length_c                   16.683(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.36(3)
_cell_angle_gamma                90.00
_cell_volume                     1635.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5947
_cell_measurement_theta_min      1.3399
_cell_measurement_theta_max      27.4795
_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5608
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9557
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2842
_reflns_number_gt                2612
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1905P)^2^+0.5395P] where P=(Fo^2^+2Fc^2^)/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         2842
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2744
_refine_ls_wR_factor_gt          0.2023
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_restrained_S_all      1.219
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003
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
Cl1 Cl -0.11686(7) 0.80125(11) 0.11147(5) 0.0313(4) Uani 1 1 d . . .
F1 F 0.44659(18) 0.7388(4) 0.45684(15) 0.0521(7) Uani 1 1 d . . .
F2 F 0.3419(2) 0.7800(4) 0.51958(14) 0.0543(8) Uani 1 1 d . . .
F3 F 0.3447(2) 0.5328(3) 0.46017(14) 0.0489(7) Uani 1 1 d . . .
N1 N -0.1256(2) 0.0978(4) -0.0655(2) 0.0354(8) Uani 1 1 d . . .
N2 N 0.1914(2) 0.6730(4) 0.32580(17) 0.0251(7) Uani 1 1 d . . .
C1 C -0.0860(3) 0.1983(4) -0.0104(2) 0.0271(8) Uani 1 1 d . . .
C2 C -0.0378(2) 0.3302(4) 0.05708(19) 0.0216(7) Uani 1 1 d . . .
C3 C -0.0942(2) 0.4819(4) 0.05342(19) 0.0231(7) Uani 1 1 d . . .
H3 H -0.1627 0.4972 0.0093 0.028 Uiso 1 1 calc R . .
C4 C -0.0470(2) 0.6104(4) 0.1165(2) 0.0223(7) Uani 1 1 d . . .
C5 C 0.0541(2) 0.5897(4) 0.18241(18) 0.0207(7) Uani 1 1 d . . .
C6 C 0.1079(2) 0.4378(4) 0.18208(19) 0.0231(7) Uani 1 1 d . . .
H6 H 0.1769 0.4227 0.2255 0.028 Uiso 1 1 calc R . .
C7 C 0.0633(3) 0.3069(4) 0.1196(2) 0.0238(8) Uani 1 1 d . . .
H7 H 0.1012 0.2039 0.1198 0.029 Uiso 1 1 calc R . .
C8 C 0.1032(3) 0.7349(5) 0.2478(2) 0.0255(8) Uani 1 1 d . . .
H8A H 0.1269 0.8286 0.2194 0.031 Uiso 1 1 calc R . .
H8B H 0.0503 0.7858 0.2658 0.031 Uiso 1 1 calc R . .
C9 C 0.2668(3) 0.7751(5) 0.3648(2) 0.0248(8) Uani 1 1 d . . .
C10 C 0.3503(3) 0.7043(5) 0.4500(2) 0.0324(9) Uani 1 1 d . . .
C11 C 0.2853(3) 0.9590(5) 0.3417(2) 0.0280(8) Uani 1 1 d . . .
H11B H 0.3296 1.0224 0.3961 0.034 Uiso 1 1 calc R . .
H11A H 0.2179 1.0214 0.3145 0.034 Uiso 1 1 calc R . .
C12 C 0.3386(3) 0.9596(5) 0.2774(2) 0.0288(8) Uani 1 1 d . . .
H12B H 0.4069 0.9003 0.3058 0.035 Uiso 1 1 calc R . .
H12A H 0.2955 0.8910 0.2245 0.035 Uiso 1 1 calc R . .
C13 C 0.3553(2) 1.1414(5) 0.2490(2) 0.0258(8) Uani 1 1 d . . .
C14 C 0.3348(3) 1.1729(5) 0.1608(2) 0.0324(9) Uani 1 1 d . . .
H14 H 0.3081 1.0812 0.1190 0.039 Uiso 1 1 calc R . .
C15 C 0.3529(3) 1.3366(6) 0.1338(2) 0.0372(9) Uani 1 1 d . . .
H15 H 0.3379 1.3557 0.0735 0.045 Uiso 1 1 calc R . .
C16 C 0.3922(3) 1.4716(5) 0.1929(2) 0.0367(9) Uani 1 1 d . . .
H16 H 0.4051 1.5830 0.1740 0.044 Uiso 1 1 calc R . .
C17 C 0.4128(3) 1.4425(5) 0.2807(3) 0.0381(9) Uani 1 1 d . . .
H17 H 0.4393 1.5351 0.3221 0.046 Uiso 1 1 calc R . .
C18 C 0.3950(3) 1.2796(5) 0.3083(2) 0.0314(9) Uani 1 1 d . . .
H18 H 0.4101 1.2614 0.3687 0.038 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0306(6) 0.0283(6) 0.0333(6) 0.0011(3) 0.0114(4) 0.0069(3)
F1 0.0280(13) 0.0790(19) 0.0402(14) 0.0037(13) 0.0047(11) -0.0039(13)
F2 0.0663(18) 0.0693(19) 0.0211(11) -0.0117(10) 0.0117(11) 0.0079(14)
F3 0.0583(16) 0.0391(15) 0.0359(13) 0.0092(10) 0.0060(11) 0.0053(12)
N1 0.0377(17) 0.0348(18) 0.0295(16) -0.0036(14) 0.0097(14) -0.0026(15)
N2 0.0277(16) 0.0302(16) 0.0178(13) -0.0043(11) 0.0097(12) -0.0052(13)
C1 0.0305(19) 0.029(2) 0.0233(17) -0.0014(13) 0.0127(15) -0.0022(15)
C2 0.0242(17) 0.0252(17) 0.0163(14) 0.0003(12) 0.0093(13) -0.0028(14)
C3 0.0213(16) 0.0292(18) 0.0170(14) 0.0002(13) 0.0061(12) -0.0038(14)
C4 0.0252(16) 0.0235(17) 0.0224(15) 0.0007(12) 0.0140(13) -0.0003(14)
C5 0.0244(16) 0.0233(17) 0.0166(14) 0.0007(12) 0.0107(12) -0.0020(14)
C6 0.0215(16) 0.0265(17) 0.0201(14) -0.0021(12) 0.0074(13) -0.0021(14)
C7 0.0256(17) 0.0237(18) 0.0221(16) -0.0025(12) 0.0097(14) 0.0011(13)
C8 0.0277(18) 0.0244(17) 0.0232(16) -0.0011(13) 0.0094(14) -0.0002(15)
C9 0.0287(18) 0.0285(19) 0.0203(16) -0.0086(13) 0.0133(14) -0.0037(15)
C10 0.033(2) 0.039(2) 0.0226(17) -0.0060(14) 0.0091(15) -0.0037(16)
C11 0.0292(18) 0.0274(19) 0.0283(17) -0.0058(14) 0.0127(14) -0.0017(15)
C12 0.0297(18) 0.0271(19) 0.0314(17) -0.0007(14) 0.0146(15) 0.0008(15)
C13 0.0193(16) 0.0295(19) 0.0324(17) -0.0002(14) 0.0146(14) -0.0009(14)
C14 0.0248(18) 0.042(2) 0.0299(18) 0.0009(15) 0.0113(15) 0.0014(16)
C15 0.0295(19) 0.050(2) 0.0318(19) 0.0105(17) 0.0121(16) 0.0004(18)
C16 0.0296(19) 0.033(2) 0.048(2) 0.0131(17) 0.0166(17) 0.0019(16)
C17 0.036(2) 0.035(2) 0.043(2) -0.0065(17) 0.0160(17) -0.0087(17)
C18 0.032(2) 0.035(2) 0.0273(18) 0.0022(14) 0.0122(15) -0.0022(16)
_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
Cl1 C4 1.740(3) . ?
F1 C10 1.341(4) . ?
F2 C10 1.346(4) . ?
F3 C10 1.326(4) . ?
N1 C1 1.150(5) . ?
N2 C9 1.261(4) . ?
N2 C8 1.459(4) . ?
C1 C2 1.453(5) . ?
C2 C7 1.388(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(5) . ?
C5 C6 1.387(5) . ?
C5 C8 1.509(4) . ?
C6 C7 1.392(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.506(5) . ?
C9 C10 1.522(5) . ?
C11 C12 1.543(4) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.516(5) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C18 1.395(5) . ?
C13 C14 1.397(5) . ?
C14 C15 1.387(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
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
C9 N2 C8 119.2(3) . . ?
N1 C1 C2 178.0(4) . . ?
C7 C2 C3 122.1(3) . . ?
C7 C2 C1 120.1(3) . . ?
C3 C2 C1 117.8(3) . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 Cl1 117.9(3) . . ?
C5 C4 Cl1 120.3(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C8 121.9(3) . . ?
C4 C5 C8 119.9(3) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C6 118.6(3) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N2 C8 C5 112.0(3) . . ?
N2 C8 H8A 109.2 . . ?
C5 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C5 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C11 129.9(3) . . ?
N2 C9 C10 115.2(3) . . ?
C11 C9 C10 114.9(3) . . ?
F3 C10 F1 107.2(3) . . ?
F3 C10 F2 106.3(3) . . ?
F1 C10 F2 106.8(3) . . ?
F3 C10 C9 114.0(3) . . ?
F1 C10 C9 112.1(3) . . ?
F2 C10 C9 110.1(3) . . ?
C9 C11 C12 111.5(3) . . ?
C9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
H11B C11 H11A 108.0 . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
H12B C12 H12A 107.7 . . ?
C18 C13 C14 117.7(3) . . ?
C18 C13 C12 122.6(3) . . ?
C14 C13 C12 119.7(3) . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.0(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
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
N1 C1 C2 C7 -144(11) . . . . ?
N1 C1 C2 C3 33(11) . . . . ?
C7 C2 C3 C4 -1.7(4) . . . . ?
C1 C2 C3 C4 -178.2(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C4 Cl1 179.4(2) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
Cl1 C4 C5 C6 -178.0(2) . . . . ?
C3 C4 C5 C8 178.2(3) . . . . ?
Cl1 C4 C5 C8 -1.3(4) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C8 C5 C6 C7 -177.8(3) . . . . ?
C3 C2 C7 C6 2.0(5) . . . . ?
C1 C2 C7 C6 178.5(3) . . . . ?
C5 C6 C7 C2 -0.5(5) . . . . ?
C9 N2 C8 C5 147.4(3) . . . . ?
C6 C5 C8 N2 -21.5(4) . . . . ?
C4 C5 C8 N2 162.0(3) . . . . ?
C8 N2 C9 C11 -3.0(5) . . . . ?
C8 N2 C9 C10 174.7(3) . . . . ?
N2 C9 C10 F3 15.1(4) . . . . ?
C11 C9 C10 F3 -166.8(3) . . . . ?
N2 C9 C10 F1 137.1(3) . . . . ?
C11 C9 C10 F1 -44.9(4) . . . . ?
N2 C9 C10 F2 -104.2(4) . . . . ?
C11 C9 C10 F2 73.8(4) . . . . ?
N2 C9 C11 C12 -86.6(4) . . . . ?
C10 C9 C11 C12 95.7(3) . . . . ?
C9 C11 C12 C13 177.7(3) . . . . ?
C11 C12 C13 C18 45.6(4) . . . . ?
C11 C12 C13 C14 -137.2(3) . . . . ?
C18 C13 C14 C15 -0.4(5) . . . . ?
C12 C13 C14 C15 -177.7(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C16 C17 C18 C13 -0.6(6) . . . . ?
C14 C13 C18 C17 0.4(5) . . . . ?
C12 C13 C18 C17 177.7(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.172
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.303