# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                                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. 
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#  fide research purposes only. It may contain copyright material 
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data_mg11031_0ma
_database_code_depnum_ccdc_archive 'CCDC 883511'
#TrackingRef '11470_web_deposit_cif_file_0_MichaelGerken_1337717578.MG11031_0ma.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H15 F4 N S'
_chemical_formula_weight         209.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.878(5)
_cell_length_b                   7.761(5)
_cell_length_c                   9.790(6)
_cell_angle_alpha                73.126(7)
_cell_angle_beta                 80.176(7)
_cell_angle_gamma                72.901(5)
_cell_volume                     475.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       colourless
_exptl_crystal_colour            plate
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 2004)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5571
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.73
_reflns_number_total             2185
_reflns_number_gt                1632
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2006)'
_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 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^)+(0.0413P)^2^+0.0226P] 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         2185
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
S1 S -0.06017(7) 0.87017(7) 0.87372(5) 0.02260(14) Uani 1 1 d . . .
F1 F -0.10894(16) 0.68665(15) 0.87404(11) 0.0276(3) Uani 1 1 d . . .
F2 F -0.27564(16) 0.93842(16) 0.95865(12) 0.0355(3) Uani 1 1 d . . .
F3 F -0.17291(16) 0.96555(16) 0.72002(12) 0.0359(3) Uani 1 1 d . . .
F4 F 0.03389(17) 0.75311(16) 1.03201(11) 0.0353(3) Uani 1 1 d . . .
N1 N 0.2510(2) 0.7370(2) 0.74876(15) 0.0186(3) Uani 1 1 d . . .
C1 C 0.3313(3) 0.5416(2) 0.82981(19) 0.0241(4) Uani 1 1 d . . .
H1A H 0.2316 0.4711 0.8320 0.029 Uiso 1 1 calc R . .
H1B H 0.3394 0.5409 0.9300 0.029 Uiso 1 1 calc R . .
C2 C 0.5397(3) 0.4385(3) 0.7727(2) 0.0334(5) Uani 1 1 d . . .
H2A H 0.5350 0.4382 0.6733 0.050 Uiso 1 1 calc R . .
H2B H 0.5757 0.3099 0.8317 0.050 Uiso 1 1 calc R . .
H2C H 0.6426 0.5012 0.7764 0.050 Uiso 1 1 calc R . .
C3 C 0.3823(3) 0.8521(3) 0.7595(2) 0.0255(4) Uani 1 1 d . . .
H3A H 0.5221 0.8020 0.7178 0.031 Uiso 1 1 calc R . .
H3B H 0.3902 0.8389 0.8622 0.031 Uiso 1 1 calc R . .
C4 C 0.3129(3) 1.0574(3) 0.6862(2) 0.0329(5) Uani 1 1 d . . .
H4A H 0.3217 1.0740 0.5824 0.049 Uiso 1 1 calc R . .
H4B H 0.4009 1.1239 0.7071 0.049 Uiso 1 1 calc R . .
H4C H 0.1713 1.1074 0.7216 0.049 Uiso 1 1 calc R . .
C5 C 0.2305(3) 0.7542(3) 0.59760(19) 0.0252(4) Uani 1 1 d . . .
H5A H 0.3691 0.7268 0.5469 0.030 Uiso 1 1 calc R . .
H5B H 0.1606 0.8852 0.5534 0.030 Uiso 1 1 calc R . .
C6 C 0.1149(3) 0.6290(3) 0.5736(2) 0.0334(5) Uani 1 1 d . . .
H6A H 0.1902 0.4984 0.6076 0.050 Uiso 1 1 calc R . .
H6B H 0.1003 0.6567 0.4711 0.050 Uiso 1 1 calc R . .
H6C H -0.0207 0.6506 0.6266 0.050 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
S1 0.0202(2) 0.0230(3) 0.0238(3) -0.00603(19) -0.00063(18) -0.00507(18)
F1 0.0268(6) 0.0289(6) 0.0300(6) -0.0075(5) 0.0031(5) -0.0148(5)
F2 0.0232(6) 0.0405(7) 0.0390(7) -0.0151(6) 0.0078(5) -0.0036(5)
F3 0.0278(6) 0.0408(7) 0.0303(7) 0.0007(5) -0.0077(5) -0.0026(5)
F4 0.0356(7) 0.0459(8) 0.0228(6) -0.0102(5) -0.0048(5) -0.0054(6)
N1 0.0205(8) 0.0185(8) 0.0174(8) -0.0025(6) -0.0040(6) -0.0067(6)
C1 0.0263(10) 0.0221(10) 0.0216(10) -0.0024(8) -0.0062(8) -0.0038(8)
C2 0.0311(11) 0.0275(11) 0.0386(12) -0.0098(10) -0.0055(9) -0.0004(9)
C3 0.0219(10) 0.0277(11) 0.0312(11) -0.0095(9) -0.0033(8) -0.0104(8)
C4 0.0302(11) 0.0271(11) 0.0428(13) -0.0066(10) 0.0012(10) -0.0143(9)
C5 0.0251(10) 0.0307(11) 0.0187(9) -0.0047(8) -0.0035(8) -0.0065(8)
C6 0.0343(12) 0.0438(13) 0.0283(11) -0.0147(10) -0.0071(9) -0.0119(10)

_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
S1 F1 1.5555(14) . ?
S1 F2 1.5943(14) . ?
S1 F4 1.6807(14) . ?
S1 F3 1.6815(14) . ?
S1 N1 2.3844(19) . ?
N1 C5 1.474(2) . ?
N1 C3 1.479(2) . ?
N1 C1 1.480(2) . ?
C1 C2 1.523(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.512(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.511(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
F1 S1 F2 91.80(7) . . ?
F1 S1 F4 86.26(7) . . ?
F2 S1 F4 88.63(7) . . ?
F1 S1 F3 86.47(7) . . ?
F2 S1 F3 88.62(7) . . ?
F4 S1 F3 172.13(6) . . ?
F1 S1 N1 81.75(6) . . ?
F2 S1 N1 173.54(6) . . ?
F4 S1 N1 90.74(7) . . ?
F3 S1 N1 91.16(7) . . ?
C5 N1 C3 110.82(14) . . ?
C5 N1 C1 112.84(15) . . ?
C3 N1 C1 109.70(15) . . ?
C5 N1 S1 113.18(11) . . ?
C3 N1 S1 100.94(12) . . ?
C1 N1 S1 108.69(10) . . ?
N1 C1 C2 116.20(15) . . ?
N1 C1 H1A 108.2 . . ?
C2 C1 H1A 108.2 . . ?
N1 C1 H1B 108.2 . . ?
C2 C1 H1B 108.2 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 115.37(16) . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 115.33(15) . . ?
N1 C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
N1 C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.73
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.053