# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


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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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#  fide research purposes only. It may contain copyright material 
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data_2
_database_code_depnum_ccdc_archive 'CCDC 892697'
#TrackingRef '2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 Cl F4 N'
_chemical_formula_sum            'C22 H22 Cl F4 N'
_chemical_formula_weight         411.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.2710(4)
_cell_length_b                   13.0197(6)
_cell_length_c                   22.3322(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2114.11(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18049
_cell_measurement_theta_min      4.0
_cell_measurement_theta_max      68.1

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26693
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         68.06
_reflns_number_total             3740
_reflns_number_gt                3597
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^ > 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. The NH hydrogen atoms were
located from a difference map and refined isotropically subject to a
distance restraint. The CF3 group on C23 showed disorder in the F atoms,
so they were refined isotropically in 4 locations each of 0.75 occupancy.
;

_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^)+(0.1152P)^2^+3.2774P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_number_reflns         3740
_refine_ls_number_parameters     250
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1918
_refine_ls_wR_factor_gt          0.1892
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.002

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 0.32515(13) 0.68206(8) 0.06409(4) 0.0356(3) Uani 1 1 d . . .
C1 C 0.8058(6) 0.4789(3) 0.05406(17) 0.0309(8) Uani 1 1 d . . .
C2 C 0.6539(6) 0.4609(3) 0.0881(2) 0.0370(9) Uani 1 1 d . . .
H2A H 0.5548 0.5084 0.0869 0.044 Uiso 1 1 calc R . .
C3 C 0.6405(6) 0.3732(4) 0.1250(2) 0.0428(11) Uani 1 1 d . . .
H3A H 0.5337 0.3626 0.1487 0.051 Uiso 1 1 calc R . .
C4 C 0.7793(6) 0.3046(3) 0.1265(2) 0.0411(10) Uani 1 1 d . . .
H4A H 0.7690 0.2459 0.1516 0.049 Uiso 1 1 calc R . .
C5 C 0.9384(6) 0.3178(3) 0.09201(19) 0.0351(9) Uani 1 1 d . . .
C6 C 1.0852(8) 0.2458(4) 0.0931(2) 0.0501(13) Uani 1 1 d . . .
H6A H 1.0755 0.1870 0.1180 0.060 Uiso 1 1 calc R . .
C7 C 1.2362(7) 0.2586(4) 0.0600(3) 0.0554(13) Uani 1 1 d . . .
H7A H 1.3317 0.2089 0.0615 0.067 Uiso 1 1 calc R . .
C8 C 1.2549(8) 0.3466(4) 0.0225(2) 0.0501(12) Uani 1 1 d . . .
H8A H 1.3624 0.3550 -0.0012 0.060 Uiso 1 1 calc R . .
C9 C 1.1196(6) 0.4183(4) 0.0205(2) 0.0393(10) Uani 1 1 d . . .
H9A H 1.1345 0.4769 -0.0043 0.047 Uiso 1 1 calc R . .
C10 C 0.9561(6) 0.4076(3) 0.05489(18) 0.0326(9) Uani 1 1 d . . .
C11 C 0.8147(7) 0.5712(3) 0.01190(17) 0.0330(9) Uani 1 1 d . . .
H11A H 0.9463 0.5830 0.0009 0.040 Uiso 1 1 calc R . .
N12 N 0.7429(5) 0.6666(2) 0.04091(14) 0.0279(7) Uani 1 1 d D . .
H12A H 0.611(3) 0.664(3) 0.0452(18) 0.021(10) Uiso 1 1 d D . .
H12B H 0.749(9) 0.719(3) 0.010(2) 0.067(18) Uiso 1 1 d D . .
C13 C 0.8432(6) 0.6969(3) 0.09685(17) 0.0314(8) Uani 1 1 d . . .
H13A H 0.8424 0.6387 0.1254 0.038 Uiso 1 1 calc R . .
H13B H 0.9729 0.7127 0.0869 0.038 Uiso 1 1 calc R . .
F14 F 0.7435(4) 0.86770(18) 0.08253(11) 0.0446(7) Uani 1 1 d . . .
C14 C 0.7562(6) 0.7892(3) 0.12590(17) 0.0308(8) Uani 1 1 d . . .
H14A H 0.6309 0.7712 0.1411 0.037 Uiso 1 1 calc R . .
C15 C 0.8755(6) 0.8276(4) 0.17704(19) 0.0385(10) Uani 1 1 d . . .
H15A H 0.9068 0.7684 0.2029 0.046 Uiso 1 1 calc R . .
H15B H 0.9919 0.8540 0.1600 0.046 Uiso 1 1 calc R . .
C16 C 0.7929(6) 0.9105(3) 0.21588(17) 0.0327(9) Uani 1 1 d . . .
C17 C 0.6370(7) 0.9647(3) 0.20082(18) 0.0391(10) Uani 1 1 d . . .
H17A H 0.5760 0.9500 0.1642 0.047 Uiso 1 1 calc R . .
C18 C 0.5668(7) 1.0411(4) 0.23859(19) 0.0431(11) Uani 1 1 d . . .
C19 C 0.6536(8) 1.0626(4) 0.2923(2) 0.0473(12) Uani 1 1 d . . .
H19A H 0.6068 1.1142 0.3182 0.057 Uiso 1 1 calc R . .
C20 C 0.8092(8) 1.0080(4) 0.3077(2) 0.0531(13) Uani 1 1 d . . .
H20A H 0.8702 1.0228 0.3444 0.064 Uiso 1 1 calc R . .
C21 C 0.8772(8) 0.9324(4) 0.2709(2) 0.0492(12) Uani 1 1 d . . .
H21A H 0.9827 0.8946 0.2828 0.059 Uiso 1 1 calc R . .
C22 C 0.7079(8) 0.5515(3) -0.0449(2) 0.0492(13) Uani 1 1 d . . .
H22A H 0.7159 0.6118 -0.0710 0.074 Uiso 1 1 calc R . .
H22B H 0.5788 0.5381 -0.0350 0.074 Uiso 1 1 calc R . .
H22C H 0.7596 0.4916 -0.0655 0.074 Uiso 1 1 calc R . .
C23 C 0.3917(12) 1.0935(5) 0.2233(2) 0.084(3) Uani 1 1 d . . .
F1 F 0.2720(8) 1.0941(4) 0.2647(3) 0.0887(16) Uiso 0.75 1 d P . .
F2 F 0.4237(10) 1.2002(6) 0.2245(3) 0.108(2) Uiso 0.75 1 d P . .
F3 F 0.2838(12) 1.0446(6) 0.1841(4) 0.125(2) Uiso 0.75 1 d P . .
F4 F 0.3989(15) 1.1210(8) 0.1654(4) 0.155(3) Uiso 0.75 1 d P . .

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 0.0265(4) 0.0443(5) 0.0359(5) 0.0130(4) 0.0021(4) 0.0051(4)
C1 0.034(2) 0.0248(17) 0.0339(19) -0.0026(15) -0.0028(17) 0.0019(16)
C2 0.032(2) 0.032(2) 0.046(2) 0.0053(18) 0.0001(19) 0.0014(18)
C3 0.038(3) 0.041(2) 0.050(2) 0.012(2) 0.003(2) -0.0026(19)
C4 0.042(3) 0.031(2) 0.050(2) 0.0061(19) -0.007(2) -0.0012(19)
C5 0.035(2) 0.0273(19) 0.043(2) -0.0060(18) -0.0111(17) 0.0028(18)
C6 0.058(3) 0.032(2) 0.060(3) -0.002(2) -0.016(3) 0.009(2)
C7 0.045(3) 0.044(2) 0.078(4) -0.014(3) -0.009(3) 0.020(2)
C8 0.039(2) 0.048(3) 0.064(3) -0.015(2) -0.001(2) 0.011(2)
C9 0.037(2) 0.038(2) 0.042(2) -0.0114(18) 0.0012(18) 0.0039(19)
C10 0.035(2) 0.0288(19) 0.034(2) -0.0090(16) -0.0051(17) 0.0027(17)
C11 0.038(2) 0.0296(19) 0.0315(19) -0.0013(15) 0.0122(18) 0.0056(18)
N12 0.0266(15) 0.0259(15) 0.0312(15) 0.0051(12) 0.0024(13) 0.0020(13)
C13 0.0287(19) 0.033(2) 0.0326(18) -0.0008(16) 0.0020(16) 0.0015(17)
F14 0.0677(17) 0.0317(12) 0.0345(12) 0.0021(9) 0.0014(12) 0.0102(12)
C14 0.0319(19) 0.0296(18) 0.0310(19) 0.0019(15) -0.0005(17) -0.0002(16)
C15 0.036(2) 0.041(2) 0.038(2) -0.0044(19) -0.0044(17) -0.0017(19)
C16 0.037(2) 0.0313(19) 0.0294(18) 0.0006(15) -0.0027(17) -0.0046(17)
C17 0.049(3) 0.041(2) 0.0272(19) -0.0028(17) -0.0040(18) 0.004(2)
C18 0.056(3) 0.043(2) 0.030(2) -0.0026(18) 0.003(2) 0.008(2)
C19 0.067(3) 0.041(2) 0.033(2) -0.0076(19) 0.001(2) 0.002(2)
C20 0.062(3) 0.059(3) 0.038(2) -0.013(2) -0.011(2) -0.010(3)
C21 0.053(3) 0.057(3) 0.037(2) 0.000(2) -0.011(2) -0.001(2)
C22 0.075(4) 0.036(2) 0.036(2) -0.0011(18) -0.001(2) 0.001(2)
C23 0.153(7) 0.072(4) 0.026(2) -0.024(2) -0.022(3) 0.061(5)

_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 1.361(6) . ?
C1 C10 1.434(6) . ?
C1 C11 1.528(5) . ?
C2 C3 1.412(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.349(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.401(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.420(6) . ?
C5 C10 1.439(6) . ?
C6 C7 1.334(8) . ?
C6 H6A 0.9500 . ?
C7 C8 1.426(8) . ?
C7 H7A 0.9500 . ?
C8 C9 1.357(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.422(6) . ?
C9 H9A 0.9500 . ?
C11 N12 1.495(5) . ?
C11 C22 1.509(6) . ?
C11 H11A 1.0000 . ?
N12 C13 1.500(5) . ?
N12 H12A 0.962(19) . ?
N12 H12B 0.97(2) . ?
C13 C14 1.505(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
F14 C14 1.411(4) . ?
C14 C15 1.519(6) . ?
C14 H14A 1.0000 . ?
C15 C16 1.509(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.377(6) . ?
C16 C21 1.402(6) . ?
C17 C18 1.401(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.385(7) . ?
C18 C23 1.484(9) . ?
C19 C20 1.379(8) . ?
C19 H19A 0.9500 . ?
C20 C21 1.375(7) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 F1 1.270(9) . ?
C23 F3 1.336(10) . ?
C23 F4 1.342(11) . ?
C23 F2 1.409(10) . ?
F2 F4 1.684(12) . ?
F3 F4 1.365(11) . ?

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 C10 120.0(4) . . ?
C2 C1 C11 120.9(4) . . ?
C10 C1 C11 119.0(4) . . ?
C1 C2 C3 121.4(4) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 C10 119.4(4) . . ?
C6 C5 C10 118.6(4) . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C8 120.3(4) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 121.5(5) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C9 C10 C1 124.5(4) . . ?
C9 C10 C5 117.7(4) . . ?
C1 C10 C5 117.8(4) . . ?
N12 C11 C22 109.0(4) . . ?
N12 C11 C1 111.8(3) . . ?
C22 C11 C1 111.2(3) . . ?
N12 C11 H11A 108.2 . . ?
C22 C11 H11A 108.2 . . ?
C1 C11 H11A 108.2 . . ?
C11 N12 C13 114.2(3) . . ?
C11 N12 H12A 111(2) . . ?
C13 N12 H12A 114(2) . . ?
C11 N12 H12B 105(4) . . ?
C13 N12 H12B 112(4) . . ?
H12A N12 H12B 98(4) . . ?
C14 C13 N12 111.4(3) . . ?
C14 C13 H13A 109.4 . . ?
N12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
N12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
F14 C14 C13 108.1(3) . . ?
F14 C14 C15 108.3(3) . . ?
C13 C14 C15 110.3(3) . . ?
F14 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
C16 C15 C14 116.1(4) . . ?
C16 C15 H15A 108.3 . . ?
C14 C15 H15A 108.3 . . ?
C16 C15 H15B 108.2 . . ?
C14 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
C17 C16 C21 118.0(4) . . ?
C17 C16 C15 123.6(4) . . ?
C21 C16 C15 118.4(4) . . ?
C16 C17 C18 121.1(4) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 C23 119.9(4) . . ?
C17 C18 C23 120.0(4) . . ?
C20 C19 C18 119.1(4) . . ?
C20 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C16 120.9(5) . . ?
C20 C21 H21A 119.6 . . ?
C16 C21 H21A 119.6 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 F3 94.5(8) . . ?
F1 C23 F4 136.6(8) . . ?
F3 C23 F4 61.3(5) . . ?
F1 C23 F2 95.3(5) . . ?
F3 C23 F2 125.4(6) . . ?
F4 C23 F2 75.4(7) . . ?
F1 C23 C18 115.0(5) . . ?
F3 C23 C18 115.8(5) . . ?
F4 C23 C18 108.1(7) . . ?
F2 C23 C18 107.9(7) . . ?
C23 F2 F4 50.5(5) . . ?
F4 F3 C23 59.6(6) . . ?
F3 F4 C23 59.1(6) . . ?
F3 F4 F2 105.8(7) . . ?
C23 F4 F2 54.1(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
C10 C1 C2 C3 0.5(6) . . . . ?
C11 C1 C2 C3 176.9(4) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
C3 C4 C5 C6 -179.7(5) . . . . ?
C3 C4 C5 C10 1.2(6) . . . . ?
C4 C5 C6 C7 179.8(5) . . . . ?
C10 C5 C6 C7 -1.1(7) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
C6 C7 C8 C9 0.5(8) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
C8 C9 C10 C1 -178.5(4) . . . . ?
C8 C9 C10 C5 0.0(6) . . . . ?
C2 C1 C10 C9 179.1(4) . . . . ?
C11 C1 C10 C9 2.7(6) . . . . ?
C2 C1 C10 C5 0.6(6) . . . . ?
C11 C1 C10 C5 -175.9(3) . . . . ?
C4 C5 C10 C9 180.0(4) . . . . ?
C6 C5 C10 C9 0.9(6) . . . . ?
C4 C5 C10 C1 -1.4(6) . . . . ?
C6 C5 C10 C1 179.5(4) . . . . ?
C2 C1 C11 N12 44.0(5) . . . . ?
C10 C1 C11 N12 -139.6(4) . . . . ?
C2 C1 C11 C22 -78.1(5) . . . . ?
C10 C1 C11 C22 98.3(5) . . . . ?
C22 C11 N12 C13 -177.7(4) . . . . ?
C1 C11 N12 C13 58.9(5) . . . . ?
C11 N12 C13 C14 -176.2(3) . . . . ?
N12 C13 C14 F14 -53.6(4) . . . . ?
N12 C13 C14 C15 -171.8(3) . . . . ?
F14 C14 C15 C16 70.2(5) . . . . ?
C13 C14 C15 C16 -171.7(3) . . . . ?
C14 C15 C16 C17 -12.9(6) . . . . ?
C14 C15 C16 C21 165.9(4) . . . . ?
C21 C16 C17 C18 1.4(7) . . . . ?
C15 C16 C17 C18 -179.8(4) . . . . ?
C16 C17 C18 C19 -0.5(7) . . . . ?
C16 C17 C18 C23 -175.9(5) . . . . ?
C17 C18 C19 C20 0.1(8) . . . . ?
C23 C18 C19 C20 175.5(6) . . . . ?
C18 C19 C20 C21 -0.6(8) . . . . ?
C19 C20 C21 C16 1.6(8) . . . . ?
C17 C16 C21 C20 -2.0(7) . . . . ?
C15 C16 C21 C20 179.2(5) . . . . ?
C19 C18 C23 F1 -47.5(9) . . . . ?
C17 C18 C23 F1 127.8(6) . . . . ?
C19 C18 C23 F3 -156.3(6) . . . . ?
C17 C18 C23 F3 19.1(10) . . . . ?
C19 C18 C23 F4 137.5(7) . . . . ?
C17 C18 C23 F4 -47.1(9) . . . . ?
C19 C18 C23 F2 57.4(7) . . . . ?
C17 C18 C23 F2 -127.2(5) . . . . ?
F1 C23 F2 F4 -136.8(8) . . . . ?
F3 C23 F2 F4 -37.5(8) . . . . ?
C18 C23 F2 F4 104.7(7) . . . . ?
F1 C23 F3 F4 142.0(7) . . . . ?
F2 C23 F3 F4 42.2(9) . . . . ?
C18 C23 F3 F4 -97.4(8) . . . . ?
C23 F3 F4 F2 -28.5(6) . . . . ?
F1 C23 F4 F3 -63.3(12) . . . . ?
F2 C23 F4 F3 -145.5(7) . . . . ?
C18 C23 F4 F3 110.1(7) . . . . ?
F1 C23 F4 F2 82.2(10) . . . . ?
F3 C23 F4 F2 145.5(7) . . . . ?
C18 C23 F4 F2 -104.4(8) . . . . ?
C23 F2 F4 F3 30.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12A Cl1 0.962(19) 2.14(2) 3.088(4) 170(3) .
N12 H12B F14 0.97(2) 2.52(6) 2.778(4) 95(4) .

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.083