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

#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F3 N O'
_chemical_formula_weight         229.20

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           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                   11.4761(16)
_cell_length_b                   10.7521(15)
_cell_length_c                   8.2871(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.476(5)
_cell_angle_gamma                90.00
_cell_volume                     1019.4(2)
_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       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_T_max  0.9829
_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_reflns_number            11618
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1793
_reflns_number_gt                1371
_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)+(0.0479P)²+0.2890P] 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         1793
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.27010(13) 0.24351(14) 0.02453(19) 0.0762(5) Uani 1 1 d . . .
N1 N 0.26091(13) 0.33192(13) 0.12805(19) 0.0512(4) Uani 1 1 d . . .
F1 F -0.03019(10) 0.52786(14) 0.28462(19) 0.0902(5) Uani 1 1 d . . .
F2 F 0.09123(12) 0.62643(14) 0.15227(18) 0.0980(5) Uani 1 1 d . . .
F3 F 0.09736(12) 0.64603(13) 0.40739(19) 0.0904(5) Uani 1 1 d . . .
C1 C 0.14392(17) 0.3597(2) 0.1778(3) 0.0696(6) Uani 1 1 d . . .
H1A H 0.1081 0.2857 0.2190 0.084 Uiso 1 1 calc R . .
H1B H 0.0940 0.3919 0.0876 0.084 Uiso 1 1 calc R . .
C2 C 0.16341(15) 0.45666(17) 0.3094(2) 0.0510(5) Uani 1 1 d . . .
H2A H 0.1530 0.4172 0.4139 0.061 Uiso 1 1 calc R . .
C3 C 0.29241(15) 0.49416(16) 0.3054(2) 0.0460(4) Uani 1 1 d . . .
H3A H 0.2990 0.5781 0.2642 0.055 Uiso 1 1 calc R . .
H3B H 0.3322 0.4901 0.4130 0.055 Uiso 1 1 calc R . .
C4 C 0.34320(15) 0.40307(15) 0.19583(19) 0.0406(4) Uani 1 1 d . . .
C5 C 0.46609(15) 0.39572(15) 0.16854(19) 0.0410(4) Uani 1 1 d . . .
C6 C 0.54301(15) 0.48128(17) 0.2475(2) 0.0475(4) Uani 1 1 d . . .
H6A H 0.5136 0.5409 0.3148 0.057 Uiso 1 1 calc R . .
C7 C 0.66097(17) 0.47915(19) 0.2280(2) 0.0569(5) Uani 1 1 d . . .
H7A H 0.7103 0.5369 0.2816 0.068 Uiso 1 1 calc R . .
C8 C 0.70574(18) 0.3914(2) 0.1291(2) 0.0610(5) Uani 1 1 d . . .
H8A H 0.7856 0.3889 0.1168 0.073 Uiso 1 1 calc R . .
C9 C 0.63217(19) 0.30743(19) 0.0483(2) 0.0596(5) Uani 1 1 d . . .
H9A H 0.6626 0.2489 -0.0195 0.072 Uiso 1 1 calc R . .
C10 C 0.51386(17) 0.30885(16) 0.0665(2) 0.0513(5) Uani 1 1 d . . .
H10A H 0.4653 0.2516 0.0106 0.062 Uiso 1 1 calc R . .
C11 C 0.08188(17) 0.5628(2) 0.2889(3) 0.0609(5) 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
O1 N1 1.2903(19) . ?
N1 C4 1.308(2) . ?
N1 C1 1.466(3) . ?
F1 C11 1.338(2) . ?
F2 C11 1.334(2) . ?
F3 C11 1.330(2) . ?
C1 C2 1.512(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C11 1.477(3) . ?
C2 C3 1.537(2) . ?
C2 H2A 0.9800 . ?
C3 C4 1.485(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.448(2) . ?
C5 C10 1.400(2) . ?
C5 C6 1.401(2) . ?
C6 C7 1.376(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.376(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.374(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 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 C4 128.53(16) . . ?
O1 N1 C1 117.49(15) . . ?
C4 N1 C1 113.98(15) . . ?
N1 C1 C2 104.85(15) . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C11 C2 C1 113.15(17) . . ?
C11 C2 C3 113.40(16) . . ?
C1 C2 C3 104.70(15) . . ?
C11 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C4 C3 C2 105.35(14) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N1 C4 C5 125.49(15) . . ?
N1 C4 C3 110.10(15) . . ?
C5 C4 C3 124.40(14) . . ?
C10 C5 C6 117.25(16) . . ?
C10 C5 C4 124.26(16) . . ?
C6 C5 C4 118.49(15) . . ?
C7 C6 C5 121.59(17) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C8 C7 C6 119.87(19) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C9 C8 C7 119.81(18) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.85(18) . . ?
C8 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C9 C10 C5 120.61(18) . . ?
C9 C10 H10A 119.7 . . ?
C5 C10 H10A 119.7 . . ?
F3 C11 F2 105.48(18) . . ?
F3 C11 F1 106.34(17) . . ?
F2 C11 F1 105.21(17) . . ?
F3 C11 C2 112.83(17) . . ?
F2 C11 C2 113.67(17) . . ?
F1 C11 C2 112.62(17) . . ?

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 174.59(16) . . . . ?
C4 N1 C1 C2 -6.0(2) . . . . ?
N1 C1 C2 C11 133.35(17) . . . . ?
N1 C1 C2 C3 9.4(2) . . . . ?
C11 C2 C3 C4 -133.51(17) . . . . ?
C1 C2 C3 C4 -9.70(19) . . . . ?
O1 N1 C4 C5 -0.7(3) . . . . ?
C1 N1 C4 C5 179.92(17) . . . . ?
O1 N1 C4 C3 178.94(17) . . . . ?
C1 N1 C4 C3 -0.4(2) . . . . ?
C2 C3 C4 N1 6.54(19) . . . . ?
C2 C3 C4 C5 -173.78(15) . . . . ?
N1 C4 C5 C10 -1.1(3) . . . . ?
C3 C4 C5 C10 179.26(16) . . . . ?
N1 C4 C5 C6 178.30(16) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
C4 C5 C6 C7 179.56(16) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C6 C5 C10 C9 1.2(2) . . . . ?
C4 C5 C10 C9 -179.43(16) . . . . ?
C1 C2 C11 F3 178.24(17) . . . . ?
C3 C2 C11 F3 -62.7(2) . . . . ?
C1 C2 C11 F2 -61.7(2) . . . . ?
C3 C2 C11 F2 57.4(2) . . . . ?
C1 C2 C11 F1 57.8(2) . . . . ?
C3 C2 C11 F1 176.89(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 973252'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F3 N'
_chemical_formula_weight         211.18

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   5.3837(8)
_cell_length_b                   7.6085(12)
_cell_length_c                   22.521(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.952(5)
_cell_angle_gamma                90.00
_cell_volume                     921.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9391
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            9386
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1607
_reflns_number_gt                1301
_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)+(0.0000P)²+3.0099P] 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         1607
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_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 0.7239(6) 0.5970(4) -0.02910(12) 0.0599(9) Uani 1 1 d . . .
F2 F 0.8233(5) 0.8673(4) -0.01951(11) 0.0514(8) Uani 1 1 d . . .
F3 F 0.4714(5) 0.7806(4) 0.00783(11) 0.0505(7) Uani 1 1 d . . .
N1 N 0.2786(6) 0.9012(4) -0.16751(14) 0.0303(8) Uani 1 1 d . . .
H1B H 0.1537 0.9550 -0.1866 0.036 Uiso 1 1 calc R . .
C1 C 0.6225(7) 0.7493(5) -0.14942(16) 0.0266(8) Uani 1 1 d . . .
H1A H 0.7698 0.6832 -0.1541 0.032 Uiso 1 1 calc R . .
C2 C 0.5226(7) 0.7952(5) -0.09473(17) 0.0285(9) Uani 1 1 d . . .
C3 C 0.3110(8) 0.8892(6) -0.10743(18) 0.0340(10) Uani 1 1 d . . .
H3A H 0.2050 0.9378 -0.0793 0.041 Uiso 1 1 calc R . .
C4 C 0.4708(7) 0.8163(5) -0.19431(16) 0.0247(8) Uani 1 1 d . . .
C5 C 0.4889(7) 0.8095(5) -0.25895(16) 0.0256(8) Uani 1 1 d . . .
C6 C 0.6845(7) 0.7198(5) -0.28346(17) 0.0288(9) Uani 1 1 d . . .
H6A H 0.8043 0.6616 -0.2580 0.035 Uiso 1 1 calc R . .
C7 C 0.7065(8) 0.7145(5) -0.34418(18) 0.0321(9) Uani 1 1 d . . .
H7A H 0.8408 0.6519 -0.3600 0.039 Uiso 1 1 calc R . .
C8 C 0.5364(8) 0.7987(5) -0.38249(18) 0.0323(9) Uani 1 1 d . . .
H8A H 0.5550 0.7965 -0.4242 0.039 Uiso 1 1 calc R . .
C9 C 0.3389(8) 0.8862(5) -0.35905(18) 0.0335(10) Uani 1 1 d . . .
H9A H 0.2190 0.9431 -0.3848 0.040 Uiso 1 1 calc R . .
C10 C 0.3151(7) 0.8912(5) -0.29809(17) 0.0292(9) Uani 1 1 d . . .
H10A H 0.1780 0.9512 -0.2826 0.035 Uiso 1 1 calc R . .
C11 C 0.6337(8) 0.7592(5) -0.03485(19) 0.0354(10) 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 C11 1.330(5) . ?
F2 C11 1.342(5) . ?
F3 C11 1.342(5) . ?
N1 C3 1.358(5) . ?
N1 C4 1.384(5) . ?
N1 H1B 0.8800 . ?
C1 C4 1.365(5) . ?
C1 C2 1.413(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.363(6) . ?
C2 C11 1.472(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.465(5) . ?
C5 C6 1.393(5) . ?
C5 C10 1.397(5) . ?
C6 C7 1.379(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.382(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.386(6) . ?
C9 H9A 0.9500 . ?
C10 H10A 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
C3 N1 C4 110.0(3) . . ?
C3 N1 H1B 125.0 . . ?
C4 N1 H1B 125.0 . . ?
C4 C1 C2 108.3(3) . . ?
C4 C1 H1A 125.9 . . ?
C2 C1 H1A 125.9 . . ?
C3 C2 C1 107.4(3) . . ?
C3 C2 C11 125.8(4) . . ?
C1 C2 C11 126.7(4) . . ?
N1 C3 C2 107.9(4) . . ?
N1 C3 H3A 126.1 . . ?
C2 C3 H3A 126.1 . . ?
C1 C4 N1 106.5(3) . . ?
C1 C4 C5 130.9(3) . . ?
N1 C4 C5 122.6(3) . . ?
C6 C5 C10 117.6(3) . . ?
C6 C5 C4 120.1(3) . . ?
C10 C5 C4 122.3(3) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 121.1(4) . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C5 121.3(4) . . ?
C9 C10 H10A 119.3 . . ?
C5 C10 H10A 119.3 . . ?
F1 C11 F3 106.9(4) . . ?
F1 C11 F2 105.9(4) . . ?
F3 C11 F2 104.8(3) . . ?
F1 C11 C2 113.0(3) . . ?
F3 C11 C2 112.6(4) . . ?
F2 C11 C2 112.9(3) . . ?

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
C4 C1 C2 C3 0.1(4) . . . . ?
C4 C1 C2 C11 -176.1(4) . . . . ?
C4 N1 C3 C2 -0.6(5) . . . . ?
C1 C2 C3 N1 0.3(5) . . . . ?
C11 C2 C3 N1 176.6(4) . . . . ?
C2 C1 C4 N1 -0.5(4) . . . . ?
C2 C1 C4 C5 179.1(4) . . . . ?
C3 N1 C4 C1 0.7(4) . . . . ?
C3 N1 C4 C5 -178.9(3) . . . . ?
C1 C4 C5 C6 1.4(6) . . . . ?
N1 C4 C5 C6 -179.0(3) . . . . ?
C1 C4 C5 C10 -178.4(4) . . . . ?
N1 C4 C5 C10 1.1(6) . . . . ?
C10 C5 C6 C7 0.9(6) . . . . ?
C4 C5 C6 C7 -179.0(4) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C9 -1.4(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C8 C9 C10 C5 0.3(6) . . . . ?
C6 C5 C10 C9 -1.2(6) . . . . ?
C4 C5 C10 C9 178.6(4) . . . . ?
C3 C2 C11 F1 140.5(4) . . . . ?
C1 C2 C11 F1 -44.0(6) . . . . ?
C3 C2 C11 F3 19.2(6) . . . . ?
C1 C2 C11 F3 -165.2(4) . . . . ?
C3 C2 C11 F2 -99.3(5) . . . . ?
C1 C2 C11 F2 76.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 973253'
#######################################################################
#
#                 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 F3 N O2 S'
_chemical_formula_weight         365.36

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.455(2)
_cell_length_b                   11.918(2)
_cell_length_c                   14.701(3)
_cell_angle_alpha                111.716(6)
_cell_angle_beta                 100.424(6)
_cell_angle_gamma                107.197(6)
_cell_volume                     1683.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9100
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            18980
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_sigmaI/netI    0.0870
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5891
_reflns_number_gt                4135
_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)+(0.0832P)²+0.0000P] 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         5891
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1776
_refine_ls_wR_factor_gt          0.1620
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
S2 S 0.24020(8) 0.19269(7) 0.18430(6) 0.0342(2) Uani 1 1 d . . .
F4 F 0.6180(2) 0.1276(2) 0.48253(19) 0.0714(7) Uani 1 1 d . . .
F5 F 0.4862(2) 0.1579(2) 0.56366(17) 0.0665(7) Uani 1 1 d . . .
F6 F 0.5996(2) 0.3138(2) 0.53959(18) 0.0674(7) Uani 1 1 d . . .
O3 O 0.1026(2) 0.1349(2) 0.15080(19) 0.0431(6) Uani 1 1 d . . .
O4 O 0.3093(2) 0.3318(2) 0.24068(18) 0.0422(6) Uani 1 1 d . . .
N2 N 0.2948(2) 0.1346(2) 0.2655(2) 0.0319(6) Uani 1 1 d . . .
C19 C 0.0196(3) -0.1269(3) 0.1445(3) 0.0413(9) Uani 1 1 d . . .
H19A H 0.0001 -0.0586 0.1888 0.050 Uiso 1 1 calc R . .
C20 C -0.0795(4) -0.2382(3) 0.0640(3) 0.0514(10) Uani 1 1 d . . .
H20A H -0.1662 -0.2453 0.0521 0.062 Uiso 1 1 calc R . .
C21 C -0.0525(4) -0.3384(4) 0.0011(3) 0.0581(12) Uani 1 1 d . . .
H21A H -0.1211 -0.4152 -0.0536 0.070 Uiso 1 1 calc R . .
C22 C 0.0739(5) -0.3289(3) 0.0166(3) 0.0591(12) Uani 1 1 d . . .
H22A H 0.0920 -0.3984 -0.0275 0.071 Uiso 1 1 calc R . .
C23 C 0.1746(4) -0.2156(3) 0.0979(3) 0.0495(10) Uani 1 1 d . . .
H23A H 0.2613 -0.2087 0.1095 0.059 Uiso 1 1 calc R . .
C24 C 0.1480(3) -0.1137(3) 0.1615(3) 0.0375(8) Uani 1 1 d . . .
C25 C 0.2566(3) 0.0021(3) 0.2501(3) 0.0348(8) Uani 1 1 d . . .
C26 C 0.3405(3) 0.0044(3) 0.3298(3) 0.0373(8) Uani 1 1 d . . .
H26A H 0.3391 -0.0698 0.3405 0.045 Uiso 1 1 calc R . .
C27 C 0.4305(3) 0.1362(3) 0.3946(2) 0.0341(8) Uani 1 1 d . . .
C28 C 0.4027(3) 0.2136(3) 0.3540(2) 0.0335(8) Uani 1 1 d . . .
H28A H 0.4487 0.3059 0.3811 0.040 Uiso 1 1 calc R . .
C29 C 0.2949(3) 0.1318(3) 0.0795(3) 0.0327(8) Uani 1 1 d . . .
C30 C 0.2117(3) 0.0181(3) -0.0102(3) 0.0414(9) Uani 1 1 d . . .
H30A H 0.1257 -0.0279 -0.0150 0.050 Uiso 1 1 calc R . .
C31 C 0.2570(4) -0.0266(3) -0.0926(3) 0.0477(10) Uani 1 1 d . . .
H31A H 0.2000 -0.1024 -0.1549 0.057 Uiso 1 1 calc R . .
C32 C 0.3838(4) 0.0371(4) -0.0861(3) 0.0474(9) Uani 1 1 d . . .
C33 C 0.4639(4) 0.1514(4) 0.0049(3) 0.0479(9) Uani 1 1 d . . .
H33A H 0.5501 0.1976 0.0103 0.058 Uiso 1 1 calc R . .
C34 C 0.4206(3) 0.1981(3) 0.0865(3) 0.0415(9) Uani 1 1 d . . .
H34A H 0.4766 0.2758 0.1477 0.050 Uiso 1 1 calc R . .
C35 C 0.4323(5) -0.0145(4) -0.1759(3) 0.0631(12) Uani 1 1 d . . .
H35A H 0.5232 0.0422 -0.1574 0.095 Uiso 1 1 calc R . .
H35B H 0.3806 -0.0148 -0.2370 0.095 Uiso 1 1 calc R . .
H35C H 0.4244 -0.1043 -0.1915 0.095 Uiso 1 1 calc R . .
C36 C 0.5339(3) 0.1846(3) 0.4932(3) 0.0418(9) Uani 1 1 d . . .
S1 S 0.74431(8) 0.54176(8) 0.44405(7) 0.0353(2) Uani 1 1 d . . .
O1 O 0.7886(2) 0.4391(2) 0.43033(19) 0.0443(6) Uani 1 1 d . . .
O2 O 0.6424(2) 0.5471(2) 0.48712(19) 0.0431(6) Uani 1 1 d . . .
F1 F 0.3886(3) 0.6228(3) 0.2067(2) 0.0841(9) Uani 1 1 d . . .
F2 F 0.5082(3) 0.6824(3) 0.1225(3) 0.0992(11) Uani 1 1 d . . .
F3 F 0.3863(2) 0.4821(3) 0.06649(19) 0.0811(8) Uani 1 1 d . . .
N1 N 0.6863(2) 0.5322(2) 0.3251(2) 0.0339(7) Uani 1 1 d . . .
C1 C 0.9828(3) 0.6220(3) 0.2647(3) 0.0412(9) Uani 1 1 d . . .
H1A H 0.9726 0.6974 0.2627 0.049 Uiso 1 1 calc R . .
C2 C 1.1014(4) 0.6125(4) 0.2720(3) 0.0504(10) Uani 1 1 d . . .
H2A H 1.1721 0.6819 0.2753 0.060 Uiso 1 1 calc R . .
C3 C 1.1181(4) 0.5037(4) 0.2745(3) 0.0500(10) Uani 1 1 d . . .
H3A H 1.2004 0.4989 0.2817 0.060 Uiso 1 1 calc R . .
C4 C 1.0136(4) 0.4018(4) 0.2664(3) 0.0505(10) Uani 1 1 d . . .
H4A H 1.0232 0.3247 0.2651 0.061 Uiso 1 1 calc R . .
C5 C 0.8949(4) 0.4107(3) 0.2600(3) 0.0437(9) Uani 1 1 d . . .
H5A H 0.8241 0.3402 0.2554 0.052 Uiso 1 1 calc R . .
C6 C 0.8780(3) 0.5211(3) 0.2603(2) 0.0351(8) Uani 1 1 d . . .
C7 C 0.7524(3) 0.5346(3) 0.2526(2) 0.0355(8) Uani 1 1 d . . .
C8 C 0.6805(3) 0.5582(3) 0.1820(3) 0.0382(8) Uani 1 1 d . . .
H8A H 0.7003 0.5646 0.1236 0.046 Uiso 1 1 calc R . .
C9 C 0.5712(3) 0.5717(3) 0.2106(3) 0.0372(8) Uani 1 1 d . . .
C10 C 0.5779(3) 0.5576(3) 0.2988(3) 0.0367(8) Uani 1 1 d . . .
H10A H 0.5185 0.5642 0.3360 0.044 Uiso 1 1 calc R . .
C11 C 0.8767(3) 0.6952(3) 0.5085(2) 0.0347(8) Uani 1 1 d . . .
C12 C 0.8534(3) 0.8087(3) 0.5386(3) 0.0397(8) Uani 1 1 d . . .
H12A H 0.7673 0.8039 0.5258 0.048 Uiso 1 1 calc R . .
C13 C 0.9574(4) 0.9297(3) 0.5878(3) 0.0441(9) Uani 1 1 d . . .
H13A H 0.9419 1.0080 0.6078 0.053 Uiso 1 1 calc R . .
C14 C 1.0840(4) 0.9385(4) 0.6083(3) 0.0461(9) Uani 1 1 d . . .
C15 C 1.1035(4) 0.8234(4) 0.5780(3) 0.0501(10) Uani 1 1 d . . .
H15A H 1.1896 0.8283 0.5924 0.060 Uiso 1 1 calc R . .
C16 C 1.0024(3) 0.7010(3) 0.5273(3) 0.0440(9) Uani 1 1 d . . .
H16A H 1.0182 0.6229 0.5060 0.053 Uiso 1 1 calc R . .
C17 C 1.1970(4) 1.0716(4) 0.6639(3) 0.0653(12) Uani 1 1 d . . .
H17A H 1.2783 1.0591 0.6716 0.098 Uiso 1 1 calc R . .
H17B H 1.1929 1.1211 0.7325 0.098 Uiso 1 1 calc R . .
H17C H 1.1927 1.1207 0.6234 0.098 Uiso 1 1 calc R . .
C18 C 0.4660(4) 0.5903(4) 0.1529(3) 0.0496(10) 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
S2 O3 1.424(2) . ?
S2 O4 1.425(2) . ?
S2 N2 1.701(3) . ?
S2 C29 1.756(4) . ?
F4 C36 1.333(4) . ?
F5 C36 1.348(4) . ?
F6 C36 1.325(4) . ?
N2 C28 1.389(4) . ?
N2 C25 1.424(4) . ?
C19 C20 1.382(5) . ?
C19 C24 1.398(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.372(6) . ?
C20 H20A 0.9500 . ?
C21 C22 1.387(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.404(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.387(5) . ?
C23 H23A 0.9500 . ?
C24 C25 1.489(4) . ?
C25 C26 1.360(4) . ?
C26 C27 1.420(4) . ?
C26 H26A 0.9500 . ?
C27 C28 1.350(5) . ?
C27 C36 1.481(5) . ?
C28 H28A 0.9500 . ?
C29 C34 1.386(5) . ?
C29 C30 1.394(4) . ?
C30 C31 1.391(5) . ?
C30 H30A 0.9500 . ?
C31 C32 1.392(6) . ?
C31 H31A 0.9500 . ?
C32 C33 1.398(5) . ?
C32 C35 1.516(6) . ?
C33 C34 1.371(5) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
S1 O1 1.421(2) . ?
S1 O2 1.431(3) . ?
S1 N1 1.703(3) . ?
S1 C11 1.761(3) . ?
F1 C18 1.339(5) . ?
F2 C18 1.328(5) . ?
F3 C18 1.335(4) . ?
N1 C10 1.385(4) . ?
N1 C7 1.419(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.397(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.380(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.385(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.484(5) . ?
C7 C8 1.370(5) . ?
C8 C9 1.425(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.359(5) . ?
C9 C18 1.467(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(5) . ?
C11 C16 1.393(5) . ?
C12 C13 1.387(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.390(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.378(5) . ?
C14 C17 1.518(5) . ?
C15 C16 1.381(5) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
O3 S2 O4 120.94(14) . . ?
O3 S2 N2 107.23(14) . . ?
O4 S2 N2 104.15(13) . . ?
O3 S2 C29 109.82(15) . . ?
O4 S2 C29 109.30(15) . . ?
N2 S2 C29 103.92(14) . . ?
C28 N2 C25 108.6(3) . . ?
C28 N2 S2 122.1(2) . . ?
C25 N2 S2 128.7(2) . . ?
C20 C19 C24 120.7(4) . . ?
C20 C19 H19A 119.7 . . ?
C24 C19 H19A 119.7 . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C21 C22 C23 119.4(4) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C23 C24 C19 119.0(3) . . ?
C23 C24 C25 118.7(3) . . ?
C19 C24 C25 122.2(3) . . ?
C26 C25 N2 106.3(3) . . ?
C26 C25 C24 128.4(3) . . ?
N2 C25 C24 125.4(3) . . ?
C25 C26 C27 108.7(3) . . ?
C25 C26 H26A 125.6 . . ?
C27 C26 H26A 125.6 . . ?
C28 C27 C26 108.5(3) . . ?
C28 C27 C36 124.6(3) . . ?
C26 C27 C36 126.8(3) . . ?
C27 C28 N2 107.9(3) . . ?
C27 C28 H28A 126.0 . . ?
N2 C28 H28A 126.0 . . ?
C34 C29 C30 120.5(3) . . ?
C34 C29 S2 119.5(3) . . ?
C30 C29 S2 120.0(3) . . ?
C31 C30 C29 118.7(3) . . ?
C31 C30 H30A 120.7 . . ?
C29 C30 H30A 120.7 . . ?
C30 C31 C32 121.5(3) . . ?
C30 C31 H31A 119.2 . . ?
C32 C31 H31A 119.2 . . ?
C31 C32 C33 118.0(4) . . ?
C31 C32 C35 120.9(4) . . ?
C33 C32 C35 121.2(4) . . ?
C34 C33 C32 121.3(4) . . ?
C34 C33 H33A 119.3 . . ?
C32 C33 H33A 119.3 . . ?
C33 C34 C29 119.9(3) . . ?
C33 C34 H34A 120.1 . . ?
C29 C34 H34A 120.1 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
F6 C36 F4 108.2(3) . . ?
F6 C36 F5 104.9(3) . . ?
F4 C36 F5 104.4(3) . . ?
F6 C36 C27 113.6(3) . . ?
F4 C36 C27 113.0(3) . . ?
F5 C36 C27 112.0(3) . . ?
O1 S1 O2 120.74(15) . . ?
O1 S1 N1 107.63(14) . . ?
O2 S1 N1 104.02(14) . . ?
O1 S1 C11 109.93(16) . . ?
O2 S1 C11 110.30(15) . . ?
N1 S1 C11 102.44(14) . . ?
C10 N1 C7 109.0(3) . . ?
C10 N1 S1 121.3(2) . . ?
C7 N1 S1 127.6(2) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 122.7(3) . . ?
C1 C6 C7 118.8(3) . . ?
C8 C7 N1 106.1(3) . . ?
C8 C7 C6 129.5(3) . . ?
N1 C7 C6 124.3(3) . . ?
C7 C8 C9 108.8(3) . . ?
C7 C8 H8A 125.6 . . ?
C9 C8 H8A 125.6 . . ?
C10 C9 C8 107.9(3) . . ?
C10 C9 C18 125.6(4) . . ?
C8 C9 C18 126.5(3) . . ?
C9 C10 N1 108.2(3) . . ?
C9 C10 H10A 125.9 . . ?
N1 C10 H10A 125.9 . . ?
C12 C11 C16 121.0(3) . . ?
C12 C11 S1 118.9(3) . . ?
C16 C11 S1 120.0(3) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 C17 121.2(4) . . ?
C13 C14 C17 120.7(4) . . ?
C14 C15 C16 122.4(3) . . ?
C14 C15 H15A 118.8 . . ?
C16 C15 H15A 118.8 . . ?
C15 C16 C11 118.2(3) . . ?
C15 C16 H16A 120.9 . . ?
C11 C16 H16A 120.9 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F2 C18 F3 105.3(4) . . ?
F2 C18 F1 107.1(3) . . ?
F3 C18 F1 104.3(3) . . ?
F2 C18 C9 112.9(3) . . ?
F3 C18 C9 113.3(3) . . ?
F1 C18 C9 113.1(3) . . ?

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
O3 S2 N2 C28 -141.4(3) . . . . ?
O4 S2 N2 C28 -12.1(3) . . . . ?
C29 S2 N2 C28 102.3(3) . . . . ?
O3 S2 N2 C25 49.1(3) . . . . ?
O4 S2 N2 C25 178.4(3) . . . . ?
C29 S2 N2 C25 -67.1(3) . . . . ?
C24 C19 C20 C21 1.4(6) . . . . ?
C19 C20 C21 C22 -0.8(6) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C22 C23 C24 C19 1.3(5) . . . . ?
C22 C23 C24 C25 177.1(3) . . . . ?
C20 C19 C24 C23 -1.7(5) . . . . ?
C20 C19 C24 C25 -177.3(3) . . . . ?
C28 N2 C25 C26 0.8(4) . . . . ?
S2 N2 C25 C26 171.4(3) . . . . ?
C28 N2 C25 C24 -177.6(3) . . . . ?
S2 N2 C25 C24 -7.0(5) . . . . ?
C23 C24 C25 C26 -57.3(5) . . . . ?
C19 C24 C25 C26 118.4(4) . . . . ?
C23 C24 C25 N2 120.8(4) . . . . ?
C19 C24 C25 N2 -63.5(5) . . . . ?
N2 C25 C26 C27 -0.1(4) . . . . ?
C24 C25 C26 C27 178.3(3) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C25 C26 C27 C36 176.2(4) . . . . ?
C26 C27 C28 N2 1.2(4) . . . . ?
C36 C27 C28 N2 -175.8(3) . . . . ?
C25 N2 C28 C27 -1.3(4) . . . . ?
S2 N2 C28 C27 -172.6(2) . . . . ?
O3 S2 C29 C34 163.0(3) . . . . ?
O4 S2 C29 C34 28.2(3) . . . . ?
N2 S2 C29 C34 -82.5(3) . . . . ?
O3 S2 C29 C30 -16.5(3) . . . . ?
O4 S2 C29 C30 -151.3(3) . . . . ?
N2 S2 C29 C30 98.0(3) . . . . ?
C34 C29 C30 C31 -0.5(5) . . . . ?
S2 C29 C30 C31 179.0(3) . . . . ?
C29 C30 C31 C32 2.0(5) . . . . ?
C30 C31 C32 C33 -2.5(5) . . . . ?
C30 C31 C32 C35 178.8(3) . . . . ?
C31 C32 C33 C34 1.6(5) . . . . ?
C35 C32 C33 C34 -179.8(4) . . . . ?
C32 C33 C34 C29 -0.2(5) . . . . ?
C30 C29 C34 C33 -0.4(5) . . . . ?
S2 C29 C34 C33 -179.9(3) . . . . ?
C28 C27 C36 F6 -0.5(5) . . . . ?
C26 C27 C36 F6 -177.0(3) . . . . ?
C28 C27 C36 F4 -124.3(4) . . . . ?
C26 C27 C36 F4 59.3(5) . . . . ?
C28 C27 C36 F5 118.1(4) . . . . ?
C26 C27 C36 F5 -58.4(5) . . . . ?
O1 S1 N1 C10 142.5(2) . . . . ?
O2 S1 N1 C10 13.3(3) . . . . ?
C11 S1 N1 C10 -101.7(3) . . . . ?
O1 S1 N1 C7 -56.0(3) . . . . ?
O2 S1 N1 C7 174.8(2) . . . . ?
C11 S1 N1 C7 59.9(3) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C2 C3 C4 C5 -2.6(6) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
C2 C1 C6 C5 -2.0(5) . . . . ?
C2 C1 C6 C7 180.0(3) . . . . ?
C10 N1 C7 C8 -1.5(3) . . . . ?
S1 N1 C7 C8 -164.9(2) . . . . ?
C10 N1 C7 C6 175.3(3) . . . . ?
S1 N1 C7 C6 12.0(4) . . . . ?
C5 C6 C7 C8 -123.5(4) . . . . ?
C1 C6 C7 C8 54.4(5) . . . . ?
C5 C6 C7 N1 60.5(4) . . . . ?
C1 C6 C7 N1 -121.6(4) . . . . ?
N1 C7 C8 C9 0.5(3) . . . . ?
C6 C7 C8 C9 -176.1(3) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C7 C8 C9 C18 -176.4(3) . . . . ?
C8 C9 C10 N1 -1.6(3) . . . . ?
C18 C9 C10 N1 175.5(3) . . . . ?
C7 N1 C10 C9 1.9(3) . . . . ?
S1 N1 C10 C9 166.6(2) . . . . ?
O1 S1 C11 C12 -173.6(3) . . . . ?
O2 S1 C11 C12 -38.0(3) . . . . ?
N1 S1 C11 C12 72.2(3) . . . . ?
O1 S1 C11 C16 7.2(3) . . . . ?
O2 S1 C11 C16 142.7(3) . . . . ?
N1 S1 C11 C16 -107.0(3) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
S1 C11 C12 C13 -178.9(3) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C12 C13 C14 C17 -178.9(3) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C17 C14 C15 C16 180.0(4) . . . . ?
C14 C15 C16 C11 -1.2(6) . . . . ?
C12 C11 C16 C15 0.6(5) . . . . ?
S1 C11 C16 C15 179.9(3) . . . . ?
C10 C9 C18 F2 136.4(4) . . . . ?
C8 C9 C18 F2 -47.1(5) . . . . ?
C10 C9 C18 F3 -104.0(4) . . . . ?
C8 C9 C18 F3 72.5(5) . . . . ?
C10 C9 C18 F1 14.5(5) . . . . ?
C8 C9 C18 F1 -169.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 982258'
