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


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# 
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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. 
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data_7d
_database_code_depnum_ccdc_archive 'CCDC 924879'
#TrackingRef '7d.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Cl F3 N O'
_chemical_formula_weight         351.74
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'
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   P121/n1
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                   11.5379(13)
_cell_length_b                   7.0208(8)
_cell_length_c                   19.335(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.958(3)
_cell_angle_gamma                90.00
_cell_volume                     1560.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27160
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3907
_reflns_number_gt                2918
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^ > 2\s(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^)+(0.0461P)^2^+0.4893P] 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     SHELXL
_refine_ls_extinction_coef       0.0009(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3907
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.04141(4) 0.75369(6) 0.034915(18) 0.03654(12) Uani 1 1 d . . .
F1 F 0.10255(10) 0.6213(2) 0.48526(5) 0.0598(4) Uani 1 1 d . . .
F2 F 0.11027(10) 0.92727(19) 0.48918(5) 0.0593(4) Uani 1 1 d . . .
F3 F 0.22593(9) 0.76073(15) 0.55756(4) 0.0389(3) Uani 1 1 d . . .
O1 O 0.20181(8) 0.77378(15) 0.37450(5) 0.0248(2) Uani 1 1 d . . .
N1 N 0.38233(10) 0.78232(16) 0.33339(6) 0.0201(2) Uani 1 1 d . . .
C1 C 0.17474(14) 0.7700(2) 0.49303(7) 0.0309(3) Uani 1 1 d . . .
C2 C 0.26406(12) 0.7689(2) 0.44149(7) 0.0237(3) Uani 1 1 d . . .
H13 H 0.3145 0.8791 0.4481 0.028 Uiso 1 1 calc R . .
H12 H 0.3113 0.6547 0.4467 0.028 Uiso 1 1 calc R . .
C3 C 0.27102(12) 0.77778(19) 0.32041(7) 0.0201(3) Uani 1 1 d . . .
C4 C 0.45197(11) 0.78588(18) 0.27854(7) 0.0186(3) Uani 1 1 d . . .
C5 C 0.57799(12) 0.79840(19) 0.30223(7) 0.0202(3) Uani 1 1 d . . .
C6 C 0.65589(12) 0.9093(2) 0.26817(7) 0.0254(3) Uani 1 1 d . . .
H8 H 0.6293 0.9773 0.2287 0.030 Uiso 1 1 calc R . .
C7 C 0.77241(13) 0.9193(2) 0.29249(8) 0.0300(3) Uani 1 1 d . . .
H9 H 0.8235 0.9918 0.2687 0.036 Uiso 1 1 calc R . .
C8 C 0.81313(13) 0.8221(2) 0.35196(8) 0.0304(3) Uani 1 1 d . . .
H1 H 0.8912 0.8294 0.3683 0.036 Uiso 1 1 calc R . .
C9 C 0.40673(12) 0.77596(18) 0.21012(7) 0.0198(3) Uani 1 1 d . . .
C10 C 0.28250(12) 0.77385(18) 0.19679(7) 0.0192(3) Uani 1 1 d . . .
C11 C 0.22617(12) 0.76848(19) 0.12848(7) 0.0222(3) Uani 1 1 d . . .
H2 H 0.2699 0.7677 0.0903 0.027 Uiso 1 1 calc R . .
C12 C 0.10748(13) 0.76449(19) 0.11927(7) 0.0239(3) Uani 1 1 d . . .
C13 C 0.03605(13) 0.76693(19) 0.17443(7) 0.0241(3) Uani 1 1 d . . .
H3 H -0.0446 0.7643 0.1662 0.029 Uiso 1 1 calc R . .
C14 C 0.08861(12) 0.77327(19) 0.24095(7) 0.0230(3) Uani 1 1 d . . .
H4 H 0.0432 0.7756 0.2784 0.028 Uiso 1 1 calc R . .
C15 C 0.21080(12) 0.77631(18) 0.25273(7) 0.0190(3) Uani 1 1 d . . .
C16 C 0.48010(13) 0.7610(2) 0.14943(7) 0.0284(3) Uani 1 1 d . . .
H5 H 0.4780 0.8799 0.1248 0.043 Uiso 1 1 calc R . .
H6 H 0.4500 0.6617 0.1188 0.043 Uiso 1 1 calc R . .
H7 H 0.5589 0.7319 0.1661 0.043 Uiso 1 1 calc R . .
C17 C 0.62007(12) 0.7020(2) 0.36263(7) 0.0236(3) Uani 1 1 d . . .
H11 H 0.5694 0.6293 0.3867 0.028 Uiso 1 1 calc R . .
C18 C 0.73654(13) 0.7136(2) 0.38705(8) 0.0292(3) Uani 1 1 d . . .
H10 H 0.7634 0.6483 0.4271 0.035 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 0.0372(2) 0.0489(3) 0.02179(18) 0.00124(16) -0.00766(14) 0.00324(17)
F1 0.0541(7) 0.0908(10) 0.0359(6) 0.0009(6) 0.0124(5) -0.0413(7)
F2 0.0602(7) 0.0840(9) 0.0358(6) 0.0036(6) 0.0151(5) 0.0443(7)
F3 0.0451(6) 0.0555(7) 0.0166(4) 0.0010(4) 0.0055(4) 0.0023(4)
O1 0.0223(5) 0.0372(6) 0.0153(4) 0.0001(4) 0.0042(4) -0.0007(4)
N1 0.0234(6) 0.0202(6) 0.0171(5) -0.0008(4) 0.0049(4) -0.0014(4)
C1 0.0312(8) 0.0424(9) 0.0197(7) 0.0006(6) 0.0055(6) 0.0012(7)
C2 0.0253(7) 0.0297(8) 0.0165(6) 0.0004(5) 0.0029(5) 0.0007(6)
C3 0.0249(7) 0.0181(6) 0.0177(6) -0.0005(5) 0.0044(5) -0.0013(5)
C4 0.0223(7) 0.0154(6) 0.0186(6) 0.0002(5) 0.0054(5) 0.0003(5)
C5 0.0244(7) 0.0172(6) 0.0194(6) -0.0037(5) 0.0033(5) 0.0000(5)
C6 0.0298(8) 0.0220(7) 0.0250(7) 0.0015(5) 0.0060(6) -0.0012(6)
C7 0.0276(8) 0.0296(8) 0.0341(8) -0.0039(6) 0.0103(6) -0.0076(6)
C8 0.0226(7) 0.0360(8) 0.0326(8) -0.0080(6) 0.0024(6) -0.0033(6)
C9 0.0247(7) 0.0168(6) 0.0185(6) 0.0013(5) 0.0049(5) 0.0017(5)
C10 0.0261(7) 0.0139(6) 0.0175(6) 0.0008(5) 0.0021(5) 0.0013(5)
C11 0.0296(7) 0.0201(7) 0.0171(6) 0.0015(5) 0.0028(5) 0.0027(5)
C12 0.0317(8) 0.0194(7) 0.0195(6) 0.0014(5) -0.0032(5) 0.0017(6)
C13 0.0235(7) 0.0223(7) 0.0261(7) 0.0019(5) -0.0006(5) 0.0007(5)
C14 0.0246(7) 0.0224(7) 0.0223(6) 0.0005(5) 0.0040(5) 0.0000(5)
C15 0.0237(7) 0.0153(6) 0.0182(6) 0.0002(5) 0.0029(5) -0.0002(5)
C16 0.0285(8) 0.0380(9) 0.0192(6) 0.0006(6) 0.0059(5) 0.0059(6)
C17 0.0262(7) 0.0253(7) 0.0197(6) -0.0010(5) 0.0043(5) -0.0048(6)
C18 0.0292(8) 0.0335(8) 0.0241(7) -0.0003(6) -0.0021(6) -0.0003(6)
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C12 1.7413(14) . ?
F1 C1 1.336(2) . ?
F2 C1 1.3296(19) . ?
F3 C1 1.3352(17) . ?
O1 C3 1.3699(16) . ?
O1 C2 1.4261(16) . ?
N1 C3 1.2875(18) . ?
N1 C4 1.3851(17) . ?
C1 C2 1.494(2) . ?
C2 H13 0.9700 . ?
C2 H12 0.9700 . ?
C3 C15 1.4276(18) . ?
C4 C9 1.3813(18) . ?
C4 C5 1.4887(19) . ?
C5 C6 1.3965(19) . ?
C5 C17 1.4000(19) . ?
C6 C7 1.387(2) . ?
C6 H8 0.9300 . ?
C7 C8 1.384(2) . ?
C7 H9 0.9300 . ?
C8 C18 1.387(2) . ?
C8 H1 0.9300 . ?
C9 C10 1.434(2) . ?
C9 C16 1.5088(19) . ?
C10 C15 1.4175(19) . ?
C10 C11 1.4212(17) . ?
C11 C12 1.366(2) . ?
C11 H2 0.9300 . ?
C12 C13 1.403(2) . ?
C13 C14 1.3744(19) . ?
C13 H3 0.9300 . ?
C14 C15 1.409(2) . ?
C14 H4 0.9300 . ?
C16 H5 0.9600 . ?
C16 H6 0.9600 . ?
C16 H7 0.9600 . ?
C17 C18 1.388(2) . ?
C17 H11 0.9300 . ?
C18 H10 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
C3 O1 C2 114.38(11) . . ?
C3 N1 C4 119.08(11) . . ?
F2 C1 F3 107.04(12) . . ?
F2 C1 F1 107.60(14) . . ?
F3 C1 F1 106.74(13) . . ?
F2 C1 C2 112.45(13) . . ?
F3 C1 C2 110.37(13) . . ?
F1 C1 C2 112.34(13) . . ?
O1 C2 C1 106.45(12) . . ?
O1 C2 H13 110.4 . . ?
C1 C2 H13 110.4 . . ?
O1 C2 H12 110.4 . . ?
C1 C2 H12 110.4 . . ?
H13 C2 H12 108.6 . . ?
N1 C3 O1 119.28(12) . . ?
N1 C3 C15 125.26(12) . . ?
O1 C3 C15 115.47(12) . . ?
C9 C4 N1 122.42(12) . . ?
C9 C4 C5 125.16(12) . . ?
N1 C4 C5 112.41(11) . . ?
C6 C5 C17 118.17(13) . . ?
C6 C5 C4 122.62(12) . . ?
C17 C5 C4 119.15(12) . . ?
C7 C6 C5 120.86(13) . . ?
C7 C6 H8 119.6 . . ?
C5 C6 H8 119.6 . . ?
C8 C7 C6 120.40(14) . . ?
C8 C7 H9 119.8 . . ?
C6 C7 H9 119.8 . . ?
C7 C8 C18 119.48(14) . . ?
C7 C8 H1 120.3 . . ?
C18 C8 H1 120.3 . . ?
C4 C9 C10 117.50(12) . . ?
C4 C9 C16 123.88(13) . . ?
C10 C9 C16 118.59(12) . . ?
C15 C10 C11 117.33(12) . . ?
C15 C10 C9 120.19(12) . . ?
C11 C10 C9 122.48(13) . . ?
C12 C11 C10 119.64(13) . . ?
C12 C11 H2 120.2 . . ?
C10 C11 H2 120.2 . . ?
C11 C12 C13 123.28(12) . . ?
C11 C12 Cl1 118.42(11) . . ?
C13 C12 Cl1 118.30(11) . . ?
C14 C13 C12 118.10(13) . . ?
C14 C13 H3 121.0 . . ?
C12 C13 H3 121.0 . . ?
C13 C14 C15 120.41(13) . . ?
C13 C14 H4 119.8 . . ?
C15 C14 H4 119.8 . . ?
C14 C15 C10 121.23(12) . . ?
C14 C15 C3 123.32(12) . . ?
C10 C15 C3 115.44(12) . . ?
C9 C16 H5 109.5 . . ?
C9 C16 H6 109.5 . . ?
H5 C16 H6 109.5 . . ?
C9 C16 H7 109.5 . . ?
H5 C16 H7 109.5 . . ?
H6 C16 H7 109.5 . . ?
C18 C17 C5 120.74(13) . . ?
C18 C17 H11 119.6 . . ?
C5 C17 H11 119.6 . . ?
C8 C18 C17 120.33(14) . . ?
C8 C18 H10 119.8 . . ?
C17 C18 H10 119.8 . . ?
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
C3 O1 C2 C1 178.60(12) . . . . ?
F2 C1 C2 O1 -62.12(16) . . . . ?
F3 C1 C2 O1 178.43(12) . . . . ?
F1 C1 C2 O1 59.44(16) . . . . ?
C4 N1 C3 O1 179.84(11) . . . . ?
C4 N1 C3 C15 -0.1(2) . . . . ?
C2 O1 C3 N1 -1.95(17) . . . . ?
C2 O1 C3 C15 177.99(11) . . . . ?
C3 N1 C4 C9 -3.03(19) . . . . ?
C3 N1 C4 C5 177.81(11) . . . . ?
C9 C4 C5 C6 39.9(2) . . . . ?
N1 C4 C5 C6 -141.01(13) . . . . ?
C9 C4 C5 C17 -142.85(14) . . . . ?
N1 C4 C5 C17 36.27(17) . . . . ?
C17 C5 C6 C7 1.8(2) . . . . ?
C4 C5 C6 C7 179.07(13) . . . . ?
C5 C6 C7 C8 -1.3(2) . . . . ?
C6 C7 C8 C18 0.3(2) . . . . ?
N1 C4 C9 C10 3.90(19) . . . . ?
C5 C4 C9 C10 -177.06(12) . . . . ?
N1 C4 C9 C16 -174.07(12) . . . . ?
C5 C4 C9 C16 5.0(2) . . . . ?
C4 C9 C10 C15 -1.80(18) . . . . ?
C16 C9 C10 C15 176.28(12) . . . . ?
C4 C9 C10 C11 178.48(12) . . . . ?
C16 C9 C10 C11 -3.44(19) . . . . ?
C15 C10 C11 C12 -0.49(18) . . . . ?
C9 C10 C11 C12 179.24(12) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C10 C11 C12 Cl1 -178.88(10) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
Cl1 C12 C13 C14 179.28(10) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C10 0.3(2) . . . . ?
C13 C14 C15 C3 -178.28(13) . . . . ?
C11 C10 C15 C14 0.09(18) . . . . ?
C9 C10 C15 C14 -179.65(12) . . . . ?
C11 C10 C15 C3 178.78(11) . . . . ?
C9 C10 C15 C3 -0.96(17) . . . . ?
N1 C3 C15 C14 -179.32(13) . . . . ?
O1 C3 C15 C14 0.73(19) . . . . ?
N1 C3 C15 C10 2.02(19) . . . . ?
O1 C3 C15 C10 -177.93(11) . . . . ?
C6 C5 C17 C18 -1.3(2) . . . . ?
C4 C5 C17 C18 -178.67(13) . . . . ?
C7 C8 C18 C17 0.2(2) . . . . ?
C5 C17 C18 C8 0.3(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046