# 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
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  from this site to visualise CIF-encoded structures and 
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data_cd212628
#TrackingRef 'web_deposit_cif_file_0_YingleLiu_1364812479.cd212628.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H23 F3 N O3 S'
_chemical_formula_weight         342.39

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.4050(12)
_cell_length_b                   9.9217(12)
_cell_length_c                   10.9244(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.544(2)
_cell_angle_gamma                90.00
_cell_volume                     934.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2832
_cell_measurement_theta_min      4.849
_cell_measurement_theta_max      52.259

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             362
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.24669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5687
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3668
_reflns_number_gt                3369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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.
;

_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^)+(0.0752P)^2^+0.0463P] 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   0.02(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3668
_refine_ls_number_parameters     227
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.029
_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
S1 S 0.67325(6) 0.13385(6) 0.61019(5) 0.05040(16) Uani 1 1 d . . .
F1 F 0.3365(3) 0.0903(2) 0.6228(3) 0.1174(9) Uani 1 1 d . B .
F2 F 0.2493(2) 0.2887(2) 0.5982(3) 0.1151(9) Uani 1 1 d . B .
F3 F 0.3050(3) 0.1870(3) 0.7810(3) 0.1345(10) Uani 1 1 d . B .
N1 N 0.5696(2) 0.26329(19) 0.6263(2) 0.0482(4) Uani 1 1 d D . .
O1 O 0.5765(2) 0.02834(19) 0.5178(2) 0.0678(5) Uani 1 1 d . . .
O2 O 0.8017(2) 0.3777(2) 0.9130(2) 0.0818(6) Uani 1 1 d . . .
O3 O 0.70632(19) 0.57658(18) 0.81800(18) 0.0604(4) Uani 1 1 d . . .
C1 C 0.5157(3) 0.2618(2) 0.7323(2) 0.0508(5) Uani 1 1 d . B .
H1 H 0.5831 0.2017 0.8028 0.061 Uiso 1 1 calc R . .
C2 C 0.5272(3) 0.4039(2) 0.7910(2) 0.0509(5) Uani 1 1 d D . .
H2 H 0.4632 0.4669 0.7218 0.061 Uiso 1 1 calc R A 1
C3 C 0.4874(14) 0.4141(19) 0.9149(10) 0.070(2) Uani 0.60 1 d PDU B 1
H3 H 0.5376 0.3583 0.9880 0.084 Uiso 0.60 1 calc PR B 1
C4 C 0.3825(7) 0.5018(6) 0.9180(6) 0.0915(13) Uani 0.75 1 d PDU B 1
H4A H 0.3321 0.5577 0.8451 0.110 Uiso 0.75 1 calc PR B 1
H4B H 0.3593 0.5073 0.9930 0.110 Uiso 0.75 1 calc PR B 1
C3' C 0.458(3) 0.415(3) 0.8893(17) 0.076(3) Uani 0.40 1 d PDU B 2
H3' H 0.3580 0.3801 0.8552 0.091 Uiso 0.40 1 calc PR B 2
C4' C 0.496(3) 0.457(2) 1.0079(18) 0.107(3) Uani 0.25 1 d PDU B 2
H4'1 H 0.5936 0.4946 1.0542 0.128 Uiso 0.25 1 calc PR B 2
H4'2 H 0.4259 0.4514 1.0483 0.128 Uiso 0.25 1 calc PR B 2
C5 C 0.3506(4) 0.2076(3) 0.6822(3) 0.0704(8) Uani 1 1 d . . .
C6 C 0.6973(3) 0.4492(3) 0.8479(2) 0.0515(5) Uani 1 1 d . B .
C7 C 0.8505(3) 0.6579(3) 0.8822(3) 0.0661(7) Uani 1 1 d . . .
C8 C 0.8954(5) 0.6594(5) 1.0292(3) 0.1052(14) Uani 1 1 d . . .
H8A H 0.8110 0.6941 1.0481 0.158 Uiso 1 1 calc R . .
H8B H 0.9849 0.7157 1.0708 0.158 Uiso 1 1 calc R . .
H8C H 0.9191 0.5694 1.0636 0.158 Uiso 1 1 calc R . .
C9 C 0.7997(5) 0.7952(4) 0.8235(6) 0.1274(19) Uani 1 1 d . . .
H9A H 0.7852 0.7950 0.7314 0.191 Uiso 1 1 calc R . .
H9B H 0.8775 0.8603 0.8716 0.191 Uiso 1 1 calc R . .
H9C H 0.7038 0.8182 0.8300 0.191 Uiso 1 1 calc R . .
C10 C 0.9763(4) 0.6041(4) 0.8450(5) 0.1006(13) Uani 1 1 d . . .
H10A H 1.0002 0.5132 0.8767 0.151 Uiso 1 1 calc R . .
H10B H 1.0673 0.6591 0.8847 0.151 Uiso 1 1 calc R . .
H10C H 0.9423 0.6054 0.7496 0.151 Uiso 1 1 calc R . .
C11 C 0.7708(3) 0.2218(2) 0.5157(3) 0.0551(6) Uani 1 1 d . . .
C12 C 0.6509(4) 0.2680(3) 0.3813(3) 0.0668(7) Uani 1 1 d . . .
H12A H 0.5894 0.3391 0.3947 0.100 Uiso 1 1 calc R . .
H12B H 0.5849 0.1936 0.3373 0.100 Uiso 1 1 calc R . .
H12C H 0.7026 0.3003 0.3270 0.100 Uiso 1 1 calc R . .
C13 C 0.8642(3) 0.3386(3) 0.6003(3) 0.0692(7) Uani 1 1 d . . .
H13A H 0.9327 0.3732 0.5622 0.104 Uiso 1 1 calc R . .
H13B H 0.9239 0.3075 0.6894 0.104 Uiso 1 1 calc R . .
H13C H 0.7948 0.4085 0.6027 0.104 Uiso 1 1 calc R . .
C14 C 0.8781(3) 0.1134(3) 0.4990(4) 0.0787(8) Uani 1 1 d . . .
H14A H 0.8169 0.0404 0.4466 0.118 Uiso 1 1 calc R . .
H14B H 0.9460 0.0805 0.5853 0.118 Uiso 1 1 calc R . .
H14C H 0.9387 0.1517 0.4548 0.118 Uiso 1 1 calc R . .
H1A H 0.519(2) 0.308(2) 0.5577(18) 0.031(5) Uiso 1 1 d D . .

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 0.0517(3) 0.0349(2) 0.0650(3) 0.0001(2) 0.0238(2) 0.0030(2)
F1 0.0954(14) 0.0661(12) 0.212(3) -0.0555(14) 0.0839(17) -0.0362(10)
F2 0.0494(9) 0.0795(13) 0.190(2) 0.0088(14) 0.0203(12) -0.0123(9)
F3 0.1377(18) 0.148(2) 0.165(2) -0.0275(18) 0.1103(18) -0.0684(18)
N1 0.0513(10) 0.0362(9) 0.0584(11) 0.0039(8) 0.0233(8) 0.0047(7)
O1 0.0775(12) 0.0429(9) 0.0921(13) -0.0149(9) 0.0436(10) -0.0135(8)
O2 0.0540(10) 0.0684(13) 0.1019(15) 0.0093(11) 0.0090(10) 0.0063(10)
O3 0.0482(9) 0.0486(9) 0.0742(10) -0.0032(8) 0.0138(8) -0.0058(7)
C1 0.0535(12) 0.0380(11) 0.0646(13) 0.0064(10) 0.0274(10) -0.0009(9)
C2 0.0456(11) 0.0451(12) 0.0646(13) -0.0022(10) 0.0247(10) -0.0002(9)
C3 0.076(5) 0.077(3) 0.068(4) -0.015(4) 0.038(4) -0.008(4)
C4 0.101(3) 0.098(3) 0.102(3) -0.012(3) 0.069(3) 0.010(3)
C3' 0.075(6) 0.081(4) 0.079(5) -0.012(5) 0.039(5) -0.014(5)
C4' 0.113(7) 0.100(6) 0.106(6) -0.008(6) 0.042(6) -0.022(6)
C5 0.0701(16) 0.0474(15) 0.112(2) -0.0108(15) 0.0552(17) -0.0139(13)
C6 0.0450(11) 0.0511(13) 0.0568(12) -0.0043(10) 0.0184(10) -0.0002(10)
C7 0.0528(12) 0.062(2) 0.0763(15) -0.0161(13) 0.0186(11) -0.0153(11)
C8 0.103(2) 0.126(4) 0.085(2) -0.045(2) 0.0356(19) -0.050(3)
C9 0.096(3) 0.065(2) 0.182(5) 0.004(3) 0.014(3) -0.030(2)
C10 0.080(2) 0.102(3) 0.137(3) -0.044(2) 0.062(2) -0.035(2)
C11 0.0510(12) 0.0447(12) 0.0752(15) -0.0104(11) 0.0312(11) -0.0059(10)
C12 0.0801(17) 0.0590(15) 0.0685(15) -0.0046(12) 0.0373(13) -0.0101(13)
C13 0.0630(14) 0.0602(16) 0.0888(19) -0.0166(14) 0.0348(13) -0.0207(13)
C14 0.0701(16) 0.066(2) 0.116(2) -0.0118(17) 0.0543(16) 0.0050(15)

_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 O1 1.4864(19) . ?
S1 N1 1.6640(19) . ?
S1 C11 1.851(3) . ?
F1 C5 1.312(3) . ?
F2 C5 1.304(4) . ?
F3 C5 1.328(4) . ?
N1 C1 1.437(3) . ?
N1 H1A 0.837(16) . ?
O2 C6 1.190(3) . ?
O3 C6 1.317(3) . ?
O3 C7 1.491(3) . ?
C1 C5 1.523(4) . ?
C1 C2 1.535(3) . ?
C1 H1 0.9800 . ?
C2 C3' 1.463(16) . ?
C2 C6 1.534(3) . ?
C2 C3 1.545(10) . ?
C2 H2 0.9800 . ?
C3 C4 1.326(13) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9300 . ?
C4 H4B 0.9300 . ?
C3' C4' 1.272(17) . ?
C3' H3' 0.9300 . ?
C4' H4'1 0.9300 . ?
C4' H4'2 0.9300 . ?
C7 C8 1.489(4) . ?
C7 C10 1.495(4) . ?
C7 C9 1.501(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.521(4) . ?
C11 C13 1.523(3) . ?
C11 C14 1.534(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 S1 N1 112.94(10) . . ?
O1 S1 C11 104.99(11) . . ?
N1 S1 C11 97.90(10) . . ?
C1 N1 S1 119.17(16) . . ?
C1 N1 H1A 118.1(14) . . ?
S1 N1 H1A 117.5(15) . . ?
C6 O3 C7 122.7(2) . . ?
N1 C1 C5 110.5(2) . . ?
N1 C1 C2 109.75(18) . . ?
C5 C1 C2 111.5(2) . . ?
N1 C1 H1 108.3 . . ?
C5 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C3' C2 C6 112.2(10) . . ?
C3' C2 C1 113.3(13) . . ?
C6 C2 C1 109.06(19) . . ?
C3' C2 C3 11.2(12) . . ?
C6 C2 C3 101.8(5) . . ?
C1 C2 C3 115.1(8) . . ?
C3' C2 H2 101.8 . . ?
C6 C2 H2 110.2 . . ?
C1 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
C4 C3 C2 120.5(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
C4' C3' C2 138(2) . . ?
C4' C3' H3' 110.8 . . ?
C2 C3' H3' 110.9 . . ?
C3' C4' H4'1 120.0 . . ?
C3' C4' H4'2 120.0 . . ?
H4'1 C4' H4'2 120.0 . . ?
F2 C5 F1 107.4(3) . . ?
F2 C5 F3 106.6(3) . . ?
F1 C5 F3 105.3(3) . . ?
F2 C5 C1 112.8(2) . . ?
F1 C5 C1 112.2(2) . . ?
F3 C5 C1 112.1(3) . . ?
O2 C6 O3 126.9(2) . . ?
O2 C6 C2 123.1(2) . . ?
O3 C6 C2 109.9(2) . . ?
C8 C7 O3 109.0(2) . . ?
C8 C7 C10 112.5(3) . . ?
O3 C7 C10 110.4(2) . . ?
C8 C7 C9 110.9(4) . . ?
O3 C7 C9 102.4(2) . . ?
C10 C7 C9 111.1(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 112.5(2) . . ?
C12 C11 C14 111.5(2) . . ?
C13 C11 C14 111.0(2) . . ?
C12 C11 S1 109.80(17) . . ?
C13 C11 S1 108.31(18) . . ?
C14 C11 S1 103.41(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O1 S1 N1 C1 92.32(19) . . . . ?
C11 S1 N1 C1 -157.68(18) . . . . ?
S1 N1 C1 C5 -95.3(2) . . . . ?
S1 N1 C1 C2 141.38(17) . . . . ?
N1 C1 C2 C3' 173.5(9) . . . . ?
C5 C1 C2 C3' 50.7(10) . . . . ?
N1 C1 C2 C6 -60.9(3) . . . . ?
C5 C1 C2 C6 176.3(2) . . . . ?
N1 C1 C2 C3 -174.5(5) . . . . ?
C5 C1 C2 C3 62.7(6) . . . . ?
C3' C2 C3 C4 -44(9) . . . . ?
C6 C2 C3 C4 115.3(12) . . . . ?
C1 C2 C3 C4 -126.9(12) . . . . ?
C6 C2 C3' C4' 5(4) . . . . ?
C1 C2 C3' C4' 129(4) . . . . ?
C3 C2 C3' C4' 27(7) . . . . ?
N1 C1 C5 F2 -68.5(3) . . . . ?
C2 C1 C5 F2 53.9(3) . . . . ?
N1 C1 C5 F1 52.9(3) . . . . ?
C2 C1 C5 F1 175.3(3) . . . . ?
N1 C1 C5 F3 171.2(2) . . . . ?
C2 C1 C5 F3 -66.5(3) . . . . ?
C7 O3 C6 O2 -10.6(4) . . . . ?
C7 O3 C6 C2 166.9(2) . . . . ?
C3' C2 C6 O2 82.6(13) . . . . ?
C1 C2 C6 O2 -43.7(3) . . . . ?
C3 C2 C6 O2 78.4(8) . . . . ?
C3' C2 C6 O3 -95.0(13) . . . . ?
C1 C2 C6 O3 138.7(2) . . . . ?
C3 C2 C6 O3 -99.2(7) . . . . ?
C6 O3 C7 C8 -58.6(4) . . . . ?
C6 O3 C7 C10 65.5(4) . . . . ?
C6 O3 C7 C9 -176.1(3) . . . . ?
O1 S1 C11 C12 52.9(2) . . . . ?
N1 S1 C11 C12 -63.44(19) . . . . ?
O1 S1 C11 C13 176.09(19) . . . . ?
N1 S1 C11 C13 59.71(19) . . . . ?
O1 S1 C11 C14 -66.1(2) . . . . ?
N1 S1 C11 C14 177.51(19) . . . . ?

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
N1 H1A O1 0.837(16) 2.382(19) 3.091(3) 142.9(19) 2_656

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038


_database_code_depnum_ccdc_archive 'CCDC 932084'
#######################################################################
#
#                 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_mo_dm13099_0m
#TrackingRef 'web_deposit_cif_file_0_YingleLiu_1364812600.mo_dm13099_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H21 F2 N O3 S'
_chemical_formula_weight         297.36

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.2446(14)
_cell_length_b                   9.5342(14)
_cell_length_c                   9.3529(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.440(2)
_cell_angle_gamma                90.00
_cell_volume                     756.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    4207
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9318
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7435
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         30.54
_reflns_number_total             4532
_reflns_number_gt                4308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-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^ > 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^)+(0.0570P)^2^+0.0600P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.17523(4) 0.73904(3) 0.63643(4) 0.01963(8) Uani 1 1 d . . .
N1 N 0.07297(14) 0.87422(13) 0.65792(14) 0.0192(2) Uani 1 1 d . . .
H1 H 0.0666 0.9535 0.6076 0.023 Uiso 1 1 calc R . .
O1 O 0.18926(13) 1.16530(13) 0.86967(14) 0.0284(2) Uani 1 1 d . . .
O2 O 0.25835(14) 0.97566(15) 1.02661(16) 0.0349(3) Uani 1 1 d . . .
O3 O 0.07063(14) 0.63286(12) 0.52564(15) 0.0288(2) Uani 1 1 d . . .
F1 F -0.22916(12) 0.74464(14) 0.78062(12) 0.0373(2) Uani 1 1 d . . .
F2 F -0.27045(11) 0.88451(11) 0.58298(13) 0.0311(2) Uani 1 1 d . . .
C1 C 0.3639(3) 1.3264(3) 0.8248(3) 0.0499(6) Uani 1 1 d . . .
H1A H 0.3494 1.2820 0.7255 0.075 Uiso 1 1 calc R . .
H1B H 0.4683 1.3702 0.8701 0.075 Uiso 1 1 calc R . .
H1C H 0.2826 1.3981 0.8069 0.075 Uiso 1 1 calc R . .
C2 C 0.3505(2) 1.2171(2) 0.9350(2) 0.0393(5) Uani 1 1 d . . .
H2A H 0.4253 1.1395 0.9463 0.047 Uiso 1 1 calc R . .
H2B H 0.3752 1.2588 1.0391 0.047 Uiso 1 1 calc R . .
C3 C 0.16161(17) 1.04322(17) 0.92415(18) 0.0234(3) Uani 1 1 d . . .
C4 C -0.01041(15) 0.99912(15) 0.83873(16) 0.0186(2) Uani 1 1 d . . .
H4 H -0.0654 1.0686 0.7544 0.022 Uiso 1 1 calc R . .
C5 C -0.09003(17) 0.99652(18) 0.95195(18) 0.0249(3) Uani 1 1 d . . .
H5 H -0.0558 0.9296 1.0339 0.030 Uiso 1 1 calc R . .
C6 C -0.2056(2) 1.0836(2) 0.9419(2) 0.0333(4) Uani 1 1 d . . .
H6A H -0.2417 1.1514 0.8609 0.040 Uiso 1 1 calc R . .
H6B H -0.2522 1.0781 1.0158 0.040 Uiso 1 1 calc R . .
C7 C -0.00616(16) 0.85557(15) 0.76423(16) 0.0184(2) Uani 1 1 d . . .
H7 H 0.0586 0.7900 0.8490 0.022 Uiso 1 1 calc R . .
C8 C -0.16704(18) 0.78947(16) 0.67851(19) 0.0237(3) Uani 1 1 d . . .
H8 H -0.1572 0.7082 0.6154 0.028 Uiso 1 1 calc R . .
C9 C 0.27668(16) 0.83155(16) 0.52906(18) 0.0216(3) Uani 1 1 d . . .
C10 C 0.15743(19) 0.88284(17) 0.37220(19) 0.0257(3) Uani 1 1 d . . .
H10A H 0.0985 0.9624 0.3884 0.039 Uiso 1 1 calc R . .
H10B H 0.0842 0.8067 0.3201 0.039 Uiso 1 1 calc R . .
H10C H 0.2129 0.9124 0.3072 0.039 Uiso 1 1 calc R . .
C11 C 0.3737(2) 0.95149(19) 0.6316(2) 0.0315(3) Uani 1 1 d . . .
H11A H 0.4414 0.9923 0.5842 0.047 Uiso 1 1 calc R . .
H11B H 0.4393 0.9152 0.7353 0.047 Uiso 1 1 calc R . .
H11C H 0.3025 1.0237 0.6409 0.047 Uiso 1 1 calc R . .
C12 C 0.38502(18) 0.71911(18) 0.5078(2) 0.0287(3) Uani 1 1 d . . .
H12A H 0.3215 0.6391 0.4511 0.043 Uiso 1 1 calc R . .
H12B H 0.4605 0.6880 0.6101 0.043 Uiso 1 1 calc R . .
H12C H 0.4422 0.7584 0.4485 0.043 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 0.02306(14) 0.01632(14) 0.02263(14) 0.00044(13) 0.01239(11) 0.00150(12)
N1 0.0246(5) 0.0173(5) 0.0205(5) 0.0017(4) 0.0139(4) 0.0024(4)
O1 0.0238(5) 0.0328(6) 0.0286(6) -0.0054(5) 0.0105(4) -0.0086(4)
O2 0.0246(5) 0.0440(7) 0.0301(6) 0.0022(5) 0.0045(5) 0.0040(5)
O3 0.0336(6) 0.0218(5) 0.0387(6) -0.0083(5) 0.0226(5) -0.0090(4)
F1 0.0387(5) 0.0417(6) 0.0401(5) 0.0026(6) 0.0247(4) -0.0134(5)
F2 0.0232(4) 0.0306(5) 0.0337(5) 0.0021(4) 0.0051(4) -0.0029(4)
C1 0.0527(12) 0.0488(12) 0.0604(14) -0.0181(11) 0.0356(11) -0.0264(10)
C2 0.0271(7) 0.0563(13) 0.0358(9) -0.0174(9) 0.0140(6) -0.0196(8)
C3 0.0198(6) 0.0289(7) 0.0224(6) -0.0050(5) 0.0092(5) -0.0004(5)
C4 0.0184(6) 0.0207(6) 0.0180(6) -0.0011(5) 0.0084(5) -0.0009(5)
C5 0.0253(6) 0.0314(8) 0.0210(6) -0.0036(5) 0.0122(5) -0.0025(6)
C6 0.0307(7) 0.0397(9) 0.0363(9) -0.0097(7) 0.0207(7) -0.0013(7)
C7 0.0212(5) 0.0181(6) 0.0189(6) 0.0008(5) 0.0110(5) -0.0007(5)
C8 0.0263(7) 0.0216(6) 0.0269(7) -0.0001(5) 0.0145(6) -0.0044(5)
C9 0.0222(6) 0.0206(6) 0.0263(7) -0.0048(5) 0.0141(5) -0.0043(5)
C10 0.0342(7) 0.0243(7) 0.0245(7) 0.0013(6) 0.0178(6) 0.0006(6)
C11 0.0309(7) 0.0278(8) 0.0393(9) -0.0131(7) 0.0177(7) -0.0106(6)
C12 0.0234(6) 0.0290(8) 0.0379(8) -0.0086(6) 0.0168(6) -0.0016(6)

_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 O3 1.4955(12) . ?
S1 N1 1.6572(13) . ?
S1 C9 1.8481(15) . ?
N1 C7 1.4609(18) . ?
N1 H1 0.8800 . ?
O1 C3 1.335(2) . ?
O1 C2 1.4545(19) . ?
O2 C3 1.205(2) . ?
F1 C8 1.3642(18) . ?
F2 C8 1.3615(19) . ?
C1 C2 1.505(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5275(19) . ?
C4 C5 1.511(2) . ?
C4 C7 1.5434(19) . ?
C4 H4 1.0000 . ?
C5 C6 1.327(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9500 . ?
C6 H6B 0.9500 . ?
C7 C8 1.518(2) . ?
C7 H7 1.0000 . ?
C8 H8 1.0000 . ?
C9 C10 1.523(2) . ?
C9 C11 1.532(2) . ?
C9 C12 1.533(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 S1 N1 111.57(7) . . ?
O3 S1 C9 105.94(7) . . ?
N1 S1 C9 97.59(6) . . ?
C7 N1 S1 116.88(10) . . ?
C7 N1 H1 121.6 . . ?
S1 N1 H1 121.6 . . ?
C3 O1 C2 117.10(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.27(17) . . ?
O1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 125.13(15) . . ?
O2 C3 C4 123.91(15) . . ?
O1 C3 C4 110.96(13) . . ?
C5 C4 C3 109.51(12) . . ?
C5 C4 C7 114.12(12) . . ?
C3 C4 C7 105.79(11) . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C7 C4 H4 109.1 . . ?
C6 C5 C4 122.90(16) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
N1 C7 C8 109.98(12) . . ?
N1 C7 C4 107.99(11) . . ?
C8 C7 C4 114.28(11) . . ?
N1 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C4 C7 H7 108.1 . . ?
F2 C8 F1 106.66(13) . . ?
F2 C8 C7 110.79(12) . . ?
F1 C8 C7 110.93(13) . . ?
F2 C8 H8 109.5 . . ?
F1 C8 H8 109.5 . . ?
C7 C8 H8 109.5 . . ?
C10 C9 C11 112.49(14) . . ?
C10 C9 C12 111.06(13) . . ?
C11 C9 C12 110.67(12) . . ?
C10 C9 S1 110.32(10) . . ?
C11 C9 S1 108.26(11) . . ?
C12 C9 S1 103.64(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
O3 S1 N1 C7 80.44(11) . . . . ?
C9 S1 N1 C7 -169.05(10) . . . . ?
C3 O1 C2 C1 162.29(16) . . . . ?
C2 O1 C3 O2 2.8(2) . . . . ?
C2 O1 C3 C4 -177.05(13) . . . . ?
O2 C3 C4 C5 64.4(2) . . . . ?
O1 C3 C4 C5 -115.78(14) . . . . ?
O2 C3 C4 C7 -59.02(19) . . . . ?
O1 C3 C4 C7 120.81(13) . . . . ?
C3 C4 C5 C6 114.24(17) . . . . ?
C7 C4 C5 C6 -127.41(17) . . . . ?
S1 N1 C7 C8 -86.23(13) . . . . ?
S1 N1 C7 C4 148.45(9) . . . . ?
C5 C4 C7 N1 179.76(11) . . . . ?
C3 C4 C7 N1 -59.79(14) . . . . ?
C5 C4 C7 C8 57.03(16) . . . . ?
C3 C4 C7 C8 177.48(13) . . . . ?
N1 C7 C8 F2 -74.28(15) . . . . ?
C4 C7 C8 F2 47.36(16) . . . . ?
N1 C7 C8 F1 167.45(12) . . . . ?
C4 C7 C8 F1 -70.91(16) . . . . ?
O3 S1 C9 C10 51.11(12) . . . . ?
N1 S1 C9 C10 -63.97(11) . . . . ?
O3 S1 C9 C11 174.60(11) . . . . ?
N1 S1 C9 C11 59.52(12) . . . . ?
O3 S1 C9 C12 -67.85(11) . . . . ?
N1 S1 C9 C12 177.08(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.063


_database_code_depnum_ccdc_archive 'CCDC 932085'
#######################################################################
#
#                 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_cd213246

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 F3 N O3 S'
_chemical_formula_weight         285.28

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.331(3)
_cell_length_b                   9.435(4)
_cell_length_c                   9.034(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.722(7)
_cell_angle_gamma                90.00
_cell_volume                     664.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2657
_cell_measurement_theta_min      4.821
_cell_measurement_theta_max      56.406

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.79802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4001
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.98
_reflns_number_total             2345
_reflns_number_gt                2282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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. 
;

_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^)+(0.0532P)^2^+0.0394P] 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   0.09(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2345
_refine_ls_number_parameters     170
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 0.01038(5) 0.92912(5) 0.44050(5) 0.04382(14) Uani 1 1 d . . .
F1 F 0.10195(19) 0.9288(2) 0.81039(16) 0.0824(4) Uani 1 1 d . . .
F2 F 0.3410(3) 1.0379(2) 0.8752(2) 0.0963(6) Uani 1 1 d . . .
F3 F 0.3323(3) 0.8262(3) 0.95388(18) 0.1002(6) Uani 1 1 d . . .
N1 N 0.21974(17) 0.9439(2) 0.54645(16) 0.0420(3) Uani 1 1 d . . .
O1 O 0.6238(2) 0.7425(2) 0.4155(2) 0.0742(5) Uani 1 1 d . . .
O2 O 0.49546(18) 0.73615(17) 0.59384(18) 0.0547(4) Uani 1 1 d . . .
O3 O -0.07481(19) 1.06515(19) 0.44761(19) 0.0623(4) Uani 1 1 d . . .
C1 C 0.5950(3) 0.7996(2) 0.5207(3) 0.0535(5) Uani 1 1 d . . .
C2 C 0.6511(2) 0.9370(3) 0.5959(2) 0.0547(4) Uani 1 1 d . . .
H2 H 0.7194 1.0020 0.5681 0.066 Uiso 1 1 calc R . .
C3 C 0.5883(2) 0.9533(3) 0.7100(2) 0.0528(5) Uani 1 1 d . . .
H3 H 0.6068 1.0317 0.7764 0.063 Uiso 1 1 calc R . .
C4 C 0.4835(2) 0.8272(2) 0.7163(2) 0.0508(4) Uani 1 1 d . . .
H4 H 0.5350 0.7801 0.8190 0.061 Uiso 1 1 calc R . .
C5 C 0.2918(2) 0.8552(2) 0.6843(2) 0.0437(4) Uani 1 1 d . . .
H5 H 0.2324 0.7638 0.6608 0.052 Uiso 1 1 calc R . .
C6 C 0.2671(3) 0.9144(3) 0.8311(2) 0.0627(6) Uani 1 1 d . . .
C7 C 0.0215(2) 0.9227(3) 0.2405(2) 0.0532(4) Uani 1 1 d . . .
C8 C 0.1130(4) 1.0523(3) 0.2109(3) 0.0732(7) Uani 1 1 d . . .
H8A H 0.2333 1.0456 0.2719 0.110 Uiso 1 1 calc R . .
H8B H 0.0667 1.1358 0.2416 0.110 Uiso 1 1 calc R . .
H8C H 0.0969 1.0578 0.1004 0.110 Uiso 1 1 calc R . .
C9 C 0.1113(4) 0.7851(3) 0.2291(3) 0.0688(7) Uani 1 1 d . . .
H9A H 0.1025 0.7698 0.1214 0.103 Uiso 1 1 calc R . .
H9B H 0.0581 0.7077 0.2632 0.103 Uiso 1 1 calc R . .
H9C H 0.2301 0.7907 0.2954 0.103 Uiso 1 1 calc R . .
C10 C -0.1671(3) 0.9188(5) 0.1316(3) 0.0922(9) Uani 1 1 d . . .
H10A H -0.2218 1.0061 0.1414 0.138 Uiso 1 1 calc R . .
H10B H -0.2238 0.8412 0.1613 0.138 Uiso 1 1 calc R . .
H10C H -0.1740 0.9068 0.0240 0.138 Uiso 1 1 calc R . .
H1 H 0.258(3) 1.030(3) 0.550(2) 0.038(5) Uiso 1 1 d . . .

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 0.03148(19) 0.0489(2) 0.0511(2) 0.0030(2) 0.01464(15) 0.0007(2)
F1 0.0745(8) 0.1145(12) 0.0758(8) -0.0057(11) 0.0481(7) 0.0055(11)
F2 0.1193(15) 0.1006(14) 0.0823(11) -0.0391(9) 0.0522(10) -0.0260(11)
F3 0.1144(13) 0.1399(17) 0.0519(8) 0.0276(9) 0.0362(8) 0.0192(13)
N1 0.0341(6) 0.0473(9) 0.0445(7) 0.0043(7) 0.0136(5) -0.0032(8)
O1 0.0709(11) 0.0666(11) 0.1011(13) -0.0128(10) 0.0499(10) 0.0036(9)
O2 0.0466(8) 0.0428(8) 0.0786(9) 0.0001(6) 0.0271(6) 0.0013(6)
O3 0.0498(8) 0.0646(10) 0.0770(10) 0.0047(8) 0.0281(7) 0.0137(7)
C1 0.0391(9) 0.0513(12) 0.0723(13) 0.0005(9) 0.0226(9) 0.0059(8)
C2 0.0373(8) 0.0510(10) 0.0768(12) 0.0001(12) 0.0213(8) -0.0013(11)
C3 0.0355(8) 0.0555(14) 0.0593(10) -0.0036(9) 0.0069(7) -0.0005(9)
C4 0.0431(9) 0.0537(11) 0.0507(10) 0.0085(9) 0.0106(7) 0.0033(9)
C5 0.0414(9) 0.0487(10) 0.0411(8) 0.0036(7) 0.0147(7) -0.0021(8)
C6 0.0638(11) 0.0803(18) 0.0478(9) 0.0022(12) 0.0243(8) -0.0036(14)
C7 0.0508(9) 0.0605(12) 0.0412(8) 0.0011(10) 0.0074(7) -0.0006(12)
C8 0.098(2) 0.0706(17) 0.0546(13) 0.0092(12) 0.0318(13) -0.0070(15)
C9 0.0815(17) 0.0703(17) 0.0542(12) -0.0107(11) 0.0232(12) 0.0036(14)
C10 0.0635(13) 0.118(3) 0.0668(14) -0.0002(18) -0.0125(11) 0.001(2)

_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 O3 1.4790(18) . ?
S1 N1 1.6721(15) . ?
S1 C7 1.843(2) . ?
F1 C6 1.328(3) . ?
F2 C6 1.312(3) . ?
F3 C6 1.339(3) . ?
N1 C5 1.443(2) . ?
N1 H1 0.86(2) . ?
O1 C1 1.189(3) . ?
O2 C1 1.367(3) . ?
O2 C4 1.432(3) . ?
C1 C2 1.462(3) . ?
C2 C3 1.319(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.489(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.542(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.518(3) . ?
C5 H5 0.9800 . ?
C7 C8 1.514(4) . ?
C7 C9 1.520(4) . ?
C7 C10 1.531(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 S1 N1 108.79(10) . . ?
O3 S1 C7 105.23(11) . . ?
N1 S1 C7 99.19(8) . . ?
C5 N1 S1 118.48(13) . . ?
C5 N1 H1 118.3(14) . . ?
S1 N1 H1 113.3(14) . . ?
C1 O2 C4 109.31(17) . . ?
O1 C1 O2 121.1(2) . . ?
O1 C1 C2 130.7(2) . . ?
O2 C1 C2 108.21(18) . . ?
C3 C2 C1 108.5(2) . . ?
C3 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
C2 C3 C4 109.7(2) . . ?
C2 C3 H3 125.2 . . ?
C4 C3 H3 125.2 . . ?
O2 C4 C3 104.33(16) . . ?
O2 C4 C5 107.98(16) . . ?
C3 C4 C5 115.98(18) . . ?
O2 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
N1 C5 C6 113.38(19) . . ?
N1 C5 C4 110.39(14) . . ?
C6 C5 C4 110.54(16) . . ?
N1 C5 H5 107.4 . . ?
C6 C5 H5 107.4 . . ?
C4 C5 H5 107.4 . . ?
F2 C6 F1 107.7(3) . . ?
F2 C6 F3 106.9(2) . . ?
F1 C6 F3 106.06(18) . . ?
F2 C6 C5 113.42(19) . . ?
F1 C6 C5 111.62(17) . . ?
F3 C6 C5 110.7(2) . . ?
C8 C7 C9 112.81(19) . . ?
C8 C7 C10 111.8(2) . . ?
C9 C7 C10 110.7(3) . . ?
C8 C7 S1 110.47(17) . . ?
C9 C7 S1 106.95(16) . . ?
C10 C7 S1 103.53(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O3 S1 N1 C5 116.52(16) . . . . ?
C7 S1 N1 C5 -133.84(16) . . . . ?
C4 O2 C1 O1 179.4(2) . . . . ?
C4 O2 C1 C2 -0.1(2) . . . . ?
O1 C1 C2 C3 -178.9(2) . . . . ?
O2 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 O2 C4 C3 -0.3(2) . . . . ?
C1 O2 C4 C5 123.60(17) . . . . ?
C2 C3 C4 O2 0.7(2) . . . . ?
C2 C3 C4 C5 -117.9(2) . . . . ?
S1 N1 C5 C6 -83.2(2) . . . . ?
S1 N1 C5 C4 152.11(15) . . . . ?
O2 C4 C5 N1 -70.0(2) . . . . ?
C3 C4 C5 N1 46.6(2) . . . . ?
O2 C4 C5 C6 163.77(19) . . . . ?
C3 C4 C5 C6 -79.6(2) . . . . ?
N1 C5 C6 F2 -61.4(2) . . . . ?
C4 C5 C6 F2 63.2(3) . . . . ?
N1 C5 C6 F1 60.5(3) . . . . ?
C4 C5 C6 F1 -175.0(2) . . . . ?
N1 C5 C6 F3 178.38(18) . . . . ?
C4 C5 C6 F3 -57.0(3) . . . . ?
O3 S1 C7 C8 55.9(2) . . . . ?
N1 S1 C7 C8 -56.5(2) . . . . ?
O3 S1 C7 C9 179.06(16) . . . . ?
N1 S1 C7 C9 66.59(18) . . . . ?
O3 S1 C7 C10 -63.9(2) . . . . ?
N1 S1 C7 C10 -176.4(2) . . . . ?

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
N1 H1 O1 0.86(2) 2.21(3) 3.072(3) 173.8(19) 2_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 938431'