# Electronic Supplementary Material (ESI) for Chemical Science.
# 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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_00713074
_audit_creation_date             2013-08-26
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H22 F3 N O2 S'
_chemical_formula_sum            'C19 H22 F3 N O2 S'
_chemical_formula_weight         385.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.7359(2)
_cell_length_b                   17.0050(4)
_cell_length_c                   9.7453(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.621(7)
_cell_angle_gamma                90.00
_cell_volume                     927.58(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11853
_cell_measurement_temperature    93
_cell_measurement_theta_max      65.0
_cell_measurement_theta_min      2.6
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R (1998) Private Communication'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD'
;
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26893
_diffrn_reflns_theta_full        65.02
_diffrn_reflns_theta_max         65.02
_diffrn_reflns_theta_min         4.65
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 220.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 50.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 125.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 55.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 225.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 300.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 250.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 320.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 110.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 150.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 75.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 350.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 0.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 275.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 25.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 175.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 0.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 325.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 165.0000
	             XTD: 42.0000
	          2theta: 42.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 275.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 100.0000
	             XTD: 42.0000
	          2theta: 90.0000
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 200.0000
	             XTD: 42.0000
	          2theta: 90.0000
;
_diffrn_measurement_device       
;
AFC11 (Left): Eulerian 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Unknown
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.075889
_diffrn_orient_matrix_UB_12      -0.021793
_diffrn_orient_matrix_UB_13      -0.094516
_diffrn_orient_matrix_UB_21      -0.160790
_diffrn_orient_matrix_UB_22      0.004369
_diffrn_orient_matrix_UB_23      0.023396
_diffrn_orient_matrix_UB_31      -0.017474
_diffrn_orient_matrix_UB_32      0.054444
_diffrn_orient_matrix_UB_33      -0.039710
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_number_gt                2923
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.036(16)
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.0314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0926
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.82 with sigma of 0.02
 N1-H1A
 0.89 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3), C13(H13), C5(H5), C11(H11), C14(H14), C2(H2), C15(H15),
 C4(H4), C1(H1B)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 -0.00811(8) 0.08331(3) 0.81924(5) 0.02187(16) Uani 1 1 d . . .
F3 F 0.5770(3) -0.13885(9) 0.96544(14) 0.0373(4) Uani 1 1 d . . .
F1 F 0.5297(3) -0.01367(9) 0.96215(14) 0.0349(4) Uani 1 1 d . . .
O1 O 0.5925(3) -0.05920(11) 0.71026(18) 0.0249(4) Uani 1 1 d D . .
F2 F 0.2277(3) -0.08948(10) 0.95799(14) 0.0362(4) Uani 1 1 d . . .
C6 C 0.3232(4) -0.16821(14) 0.6966(2) 0.0206(5) Uani 1 1 d . . .
C12 C -0.1485(4) -0.05208(17) 0.2945(3) 0.0296(6) Uani 1 1 d . . .
H12 H -0.2916 -0.0723 0.2428 0.036 Uiso 1 1 calc R . .
C3 C 0.2275(4) -0.32441(15) 0.6104(3) 0.0286(5) Uani 1 1 d . . .
H3 H 0.1969 -0.3763 0.5822 0.034 Uiso 1 1 calc R . .
N1 N 0.1973(3) 0.05144(12) 0.7364(2) 0.0218(4) Uani 1 1 d D . .
C7 C 0.3780(4) -0.08347(14) 0.7457(2) 0.0213(5) Uani 1 1 d . . .
C13 C 0.0110(5) -0.01720(16) 0.2256(3) 0.0305(6) Uani 1 1 d . . .
H13 H -0.0245 -0.0134 0.1281 0.037 Uiso 1 1 calc R . .
C5 C 0.1293(4) -0.20831(15) 0.7274(3) 0.0260(5) Uani 1 1 d . . .
H5 H 0.0295 -0.1828 0.7765 0.031 Uiso 1 1 calc R . .
C11 C -0.0970(4) -0.05726(15) 0.4405(2) 0.0247(5) Uani 1 1 d . . .
H11 H -0.2059 -0.0808 0.4857 0.030 Uiso 1 1 calc R . .
C10 C 0.1161(4) -0.02754(13) 0.5189(2) 0.0207(5) Uani 1 1 d . . .
C14 C 0.2244(5) 0.01203(17) 0.3035(3) 0.0320(6) Uani 1 1 d . . .
H14 H 0.3341 0.0345 0.2577 0.038 Uiso 1 1 calc R . .
C16 C 0.1228(4) 0.18161(15) 0.8680(2) 0.0255(5) Uani 1 1 d . . .
C2 C 0.4177(5) -0.28413(16) 0.5779(3) 0.0318(6) Uani 1 1 d . . .
H2 H 0.5143 -0.3092 0.5262 0.038 Uiso 1 1 calc R . .
C8 C 0.4253(4) -0.08105(15) 0.9077(2) 0.0265(5) Uani 1 1 d . . .
C18 C 0.1958(5) 0.22295(17) 0.7447(3) 0.0348(6) Uani 1 1 d . . .
H18A H 0.3318 0.1967 0.7232 0.052 Uiso 1 1 calc R . .
H18B H 0.2362 0.2767 0.7694 0.052 Uiso 1 1 calc R . .
H18C H 0.0654 0.2214 0.6640 0.052 Uiso 1 1 calc R . .
C15 C 0.2767(4) 0.00819(16) 0.4493(3) 0.0272(6) Uani 1 1 d . . .
H15 H 0.4186 0.0294 0.5006 0.033 Uiso 1 1 calc R . .
C4 C 0.0830(5) -0.28571(15) 0.6859(3) 0.0300(6) Uani 1 1 d . . .
H4 H -0.0456 -0.3119 0.7088 0.036 Uiso 1 1 calc R . .
C9 C 0.1629(4) -0.02963(14) 0.6787(2) 0.0198(5) Uani 1 1 d . . .
H9 H 0.0201 -0.0513 0.7045 0.024 Uiso 1 1 calc R . .
C19 C 0.3354(4) 0.16696(16) 0.9900(3) 0.0321(6) Uani 1 1 d . . .
H19A H 0.2822 0.1400 1.0642 0.048 Uiso 1 1 calc R . .
H19B H 0.4058 0.2163 1.0244 0.048 Uiso 1 1 calc R . .
H19C H 0.4518 0.1353 0.9582 0.048 Uiso 1 1 calc R . .
C1 C 0.4672(4) -0.20697(15) 0.6211(3) 0.0267(5) Uani 1 1 d . . .
H1B H 0.5975 -0.1812 0.5994 0.032 Uiso 1 1 calc R . .
C17 C -0.0725(5) 0.22743(17) 0.9150(3) 0.0388(7) Uani 1 1 d . . .
H17A H -0.2040 0.2352 0.8363 0.058 Uiso 1 1 calc R . .
H17B H -0.0113 0.2776 0.9514 0.058 Uiso 1 1 calc R . .
H17C H -0.1261 0.1986 0.9869 0.058 Uiso 1 1 calc R . .
O2 O -0.2433(3) 0.09498(10) 0.71852(17) 0.0277(4) Uani 1 1 d . . .
H1A H 0.226(5) 0.0851(15) 0.674(2) 0.027(7) Uiso 1 1 d D . .
H1 H 0.617(7) -0.0115(12) 0.724(4) 0.070(13) 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 0.0217(3) 0.0204(3) 0.0248(3) -0.0022(2) 0.0078(2) -0.0010(2)
F3 0.0495(9) 0.0264(8) 0.0292(7) 0.0014(6) -0.0062(7) 0.0095(6)
F1 0.0477(9) 0.0239(8) 0.0270(7) -0.0048(6) -0.0053(6) -0.0004(6)
O1 0.0181(7) 0.0226(10) 0.0347(9) -0.0007(7) 0.0071(7) -0.0024(7)
F2 0.0474(9) 0.0389(10) 0.0255(7) 0.0013(7) 0.0153(6) -0.0002(7)
C6 0.0225(10) 0.0186(12) 0.0199(11) -0.0001(9) 0.0031(8) 0.0022(9)
C12 0.0291(13) 0.0324(15) 0.0256(12) -0.0034(10) 0.0020(10) 0.0021(10)
C3 0.0325(13) 0.0191(13) 0.0328(13) -0.0029(11) 0.0042(10) -0.0029(10)
N1 0.0277(11) 0.0161(10) 0.0236(10) -0.0022(8) 0.0096(8) -0.0023(8)
C7 0.0218(11) 0.0187(12) 0.0239(11) -0.0008(9) 0.0062(9) -0.0027(9)
C13 0.0403(14) 0.0309(15) 0.0206(12) -0.0005(10) 0.0072(10) 0.0101(11)
C5 0.0274(12) 0.0210(14) 0.0311(13) -0.0016(10) 0.0096(10) 0.0004(9)
C11 0.0268(12) 0.0218(13) 0.0261(12) 0.0004(9) 0.0071(10) -0.0002(9)
C10 0.0236(11) 0.0167(11) 0.0233(11) 0.0003(9) 0.0082(9) 0.0028(9)
C14 0.0299(13) 0.0385(16) 0.0307(13) 0.0072(11) 0.0133(11) 0.0046(11)
C16 0.0279(12) 0.0209(13) 0.0286(12) -0.0075(10) 0.0083(10) -0.0004(10)
C2 0.0348(13) 0.0277(15) 0.0354(14) -0.0065(11) 0.0130(11) 0.0047(10)
C8 0.0299(12) 0.0224(13) 0.0248(12) -0.0005(10) 0.0010(10) 0.0026(10)
C18 0.0428(15) 0.0256(14) 0.0360(14) -0.0014(11) 0.0089(12) -0.0065(11)
C15 0.0256(12) 0.0304(15) 0.0252(13) 0.0028(10) 0.0047(10) -0.0004(10)
C4 0.0311(12) 0.0244(14) 0.0341(14) 0.0021(11) 0.0064(10) -0.0067(10)
C9 0.0192(10) 0.0196(12) 0.0212(12) -0.0016(9) 0.0059(9) -0.0008(8)
C19 0.0335(13) 0.0257(14) 0.0347(14) -0.0055(12) 0.0021(11) -0.0027(11)
C1 0.0270(12) 0.0226(14) 0.0322(14) -0.0019(11) 0.0103(10) -0.0012(10)
C17 0.0329(14) 0.0301(16) 0.0557(18) -0.0184(13) 0.0148(12) -0.0034(11)
O2 0.0215(7) 0.0250(10) 0.0358(9) -0.0023(8) 0.0047(6) -0.0003(7)

_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 N1 1.658(2) . ?
S1 C16 1.851(3) . ?
S1 O2 1.4979(16) . ?
F3 C8 1.351(3) . ?
F1 C8 1.347(3) . ?
O1 C7 1.410(3) . ?
F2 C8 1.337(3) . ?
C6 C7 1.529(3) . ?
C6 C5 1.392(3) . ?
C6 C1 1.387(3) . ?
C12 C13 1.381(4) . ?
C12 C11 1.391(3) . ?
C3 C2 1.382(4) . ?
C3 C4 1.389(4) . ?
N1 C9 1.486(3) . ?
C7 C8 1.542(3) . ?
C7 C9 1.560(3) . ?
C13 C14 1.384(4) . ?
C5 C4 1.385(4) . ?
C11 C10 1.388(3) . ?
C10 C15 1.397(3) . ?
C10 C9 1.522(3) . ?
C14 C15 1.387(4) . ?
C16 C18 1.528(4) . ?
C16 C19 1.526(3) . ?
C16 C17 1.515(3) . ?
C2 C1 1.388(4) . ?

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
N1 S1 C16 97.39(10) . . ?
O2 S1 N1 110.99(9) . . ?
O2 S1 C16 107.77(11) . . ?
C5 C6 C7 120.9(2) . . ?
C1 C6 C7 120.5(2) . . ?
C1 C6 C5 118.6(2) . . ?
C13 C12 C11 120.6(2) . . ?
C2 C3 C4 118.6(2) . . ?
C9 N1 S1 115.96(15) . . ?
O1 C7 C6 109.25(18) . . ?
O1 C7 C8 105.97(17) . . ?
O1 C7 C9 112.20(19) . . ?
C6 C7 C8 108.89(19) . . ?
C6 C7 C9 109.40(18) . . ?
C8 C7 C9 111.03(18) . . ?
C12 C13 C14 119.2(2) . . ?
C4 C5 C6 120.9(2) . . ?
C10 C11 C12 120.3(2) . . ?
C11 C10 C15 119.1(2) . . ?
C11 C10 C9 119.5(2) . . ?
C15 C10 C9 121.3(2) . . ?
C13 C14 C15 120.8(2) . . ?
C18 C16 S1 112.28(17) . . ?
C19 C16 S1 105.24(17) . . ?
C19 C16 C18 112.2(2) . . ?
C17 C16 S1 104.87(17) . . ?
C17 C16 C18 110.4(2) . . ?
C17 C16 C19 111.5(2) . . ?
C3 C2 C1 121.2(2) . . ?
F3 C8 C7 111.10(19) . . ?
F1 C8 F3 105.33(18) . . ?
F1 C8 C7 112.93(19) . . ?
F2 C8 F3 106.83(19) . . ?
F2 C8 F1 106.63(19) . . ?
F2 C8 C7 113.48(18) . . ?
C14 C15 C10 120.0(2) . . ?
C5 C4 C3 120.4(2) . . ?
N1 C9 C7 111.01(18) . . ?
N1 C9 C10 110.16(18) . . ?
C10 C9 C7 112.86(19) . . ?
C6 C1 C2 120.3(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 977759'
