# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2002


data_global

_journal_coden_Cambridge         207

loop_
_publ_author_name
'Michael F. Greaney'
'Jeremy J. Edmunds'
'Jonathan Steed'
'William Motherwell'

_publ_contact_author_name        'Prof William Motherwell'
_publ_contact_author_address     
;
Chemistry
University College London
20 Gordon St
London
WC1H OAJ
UNITED KINGDOM
;

_publ_contact_author_email       W.B.MOTHERWELL@UCL.AC.UK

_publ_requested_journal          'Perkin Transactions 1'

_publ_section_title              
;
Fluorination of sulfanyl amides using Difluoroiodoarene reagents
;

data_MFG221A
_database_code_CSD               197047

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            mfg221
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 F2 N O S'
_chemical_formula_weight         257.29

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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   14.3816(12)
_cell_length_b                   9.2890(9)
_cell_length_c                   9.0729(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1212.05(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8980
_exptl_absorpt_correction_T_max  0.9344
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
Data were corrected for decay and absorption using the program Scalepack
Z. Otwinowski and W. Minor, in Methods in Enzymology, ed. C. W. Carter and
R. M. Sweet, Academic Press: London, 1997, vol. 276, pp 307.
;

_diffrn_ambient_temperature      100(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  'Nonius KappaCCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            2617
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1457
_reflns_number_gt                1129
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1999)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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^)+(0.0288P)^2^+0.7420P] 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     SHELXL
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1457
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.23043(15) 0.4435(2) 1.1169(2) 0.0404(6) Uani 0.50 1 d P A -1
O1 O 0.39853(15) 0.2723(14) 1.1897(2) 0.037(2) Uani 0.50 1 d P A -1
N1 N 0.29799(16) 0.233(2) 1.3831(3) 0.021(3) Uani 0.50 1 d P A -1
C1 C 0.3187(2) 0.2718(12) 1.2391(4) 0.025(2) Uani 0.50 1 d P A -1
S1 S 0.26909(6) 0.21262(11) 0.95946(9) 0.0381(4) Uani 0.50 1 d P A -1
F2 F 0.14117(17) 0.0962(3) 1.1948(2) 0.0496(7) Uani 0.50 1 d P B -1
C2 C 0.2372(2) 0.2917(3) 1.1320(4) 0.0276(9) Uani 0.50 1 d P A -1
C3 C 0.14299(17) 0.2500 1.1912(3) 0.0331(6) Uani 1 2 d S . .
H3 H 0.0926 0.2876 1.1256 0.040 Uiso 0.50 1 calc PR B .
C4 C 0.1303(2) 0.3042(4) 1.3449(4) 0.0363(10) Uani 0.50 1 d P A -1
H4A H 0.0677 0.2777 1.3810 0.044 Uiso 0.50 1 calc PR A -1
H4B H 0.1354 0.4105 1.3460 0.044 Uiso 0.50 1 calc PR A -1
C5 C 0.2044(2) 0.239(3) 1.4461(3) 0.030(2) Uani 0.50 1 d P A -1
H5A H 0.2067 0.2961 1.5382 0.036 Uiso 0.50 1 calc PR A -1
H5B H 0.1852 0.1401 1.4726 0.036 Uiso 0.50 1 calc PR A -1
C6 C 0.3749(2) 0.245(3) 1.4892(3) 0.0390(12) Uani 1 2 d S A -1
H6A H 0.4291 0.2878 1.4408 0.058 Uiso 0.50 1 calc PR A -1
H6B H 0.3911 0.1486 1.5254 0.058 Uiso 0.50 1 calc PR A -1
H6C H 0.3557 0.3054 1.5723 0.058 Uiso 0.50 1 calc PR A -1
C8 C 0.1402(9) 0.380(2) 0.813(2) 0.041(3) Uani 0.50 1 d P A -1
H8 H 0.1767 0.4606 0.8431 0.049 Uiso 0.50 1 calc PR A -1
C9 C 0.0613(7) 0.4043(10) 0.7248(12) 0.043(2) Uani 0.50 1 d P A -1
H9 H 0.0441 0.4988 0.6957 0.051 Uiso 0.50 1 calc PR A -1
C10 C 0.0099(4) 0.2870(6) 0.6818(5) 0.040(3) Uani 0.50 1 d P A -1
H10 H -0.0436 0.3003 0.6221 0.048 Uiso 0.50 1 calc PR A -1
C11 C 0.0352(6) 0.1512(9) 0.7240(12) 0.049(3) Uani 0.50 1 d P A -1
H11 H -0.0013 0.0716 0.6924 0.058 Uiso 0.50 1 calc PR A -1
C12 C 0.1123(8) 0.127(2) 0.812(2) 0.044(3) Uani 0.50 1 d P A -1
H12 H 0.1295 0.0321 0.8405 0.053 Uiso 0.50 1 calc PR A -1
C7 C 0.16507(18) 0.2500 0.8566(3) 0.0337(7) Uani 1 2 d S . .

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
F1 0.0476(13) 0.0351(13) 0.0384(11) 0.0050(10) -0.0114(10) 0.0001(11)
O1 0.0227(9) 0.051(8) 0.0359(11) -0.0005(16) 0.0034(8) -0.0003(15)
N1 0.0228(10) 0.015(9) 0.0249(10) 0.0008(16) -0.0026(8) 0.0001(16)
C1 0.0256(13) 0.019(7) 0.0312(14) 0.0019(16) 0.0005(11) -0.0010(15)
S1 0.0326(4) 0.0568(11) 0.0249(4) 0.0006(4) 0.0025(3) 0.0129(4)
F2 0.0616(15) 0.0504(16) 0.0368(12) -0.0036(11) 0.0059(11) -0.0206(13)
C2 0.0293(16) 0.030(2) 0.0240(15) 0.0043(12) 0.0004(13) 0.0017(12)
C3 0.0255(12) 0.0470(17) 0.0268(12) 0.000 0.0001(10) 0.000
C4 0.0243(16) 0.058(3) 0.0267(17) -0.0004(15) 0.0021(14) 0.0051(15)
C5 0.0291(12) 0.040(6) 0.0217(12) -0.003(3) 0.0013(10) 0.002(4)
C6 0.0306(15) 0.055(3) 0.0315(14) 0.006(8) -0.0078(12) -0.012(7)
C8 0.042(6) 0.053(4) 0.027(4) -0.006(3) -0.012(5) 0.002(5)
C9 0.045(4) 0.051(6) 0.032(3) -0.011(4) -0.007(3) 0.011(3)
C10 0.0249(18) 0.069(10) 0.026(2) -0.006(2) 0.0005(15) -0.003(2)
C11 0.050(7) 0.059(8) 0.036(4) -0.003(5) 0.006(4) -0.024(5)
C12 0.060(8) 0.040(4) 0.033(5) 0.006(3) 0.003(7) -0.015(6)
C7 0.0298(13) 0.0524(19) 0.0189(11) 0.000 0.0030(10) 0.000

_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 C2 1.420(4) . ?
O1 C1 1.232(4) . ?
N1 C1 1.386(7) . ?
N1 C5 1.464(4) . ?
N1 C6 1.470(4) . ?
C1 C2 1.534(5) . ?
S1 C2 1.789(3) . ?
S1 C7 1.797(3) . ?
F2 C3 1.429(3) . ?
C2 C3 1.508(4) . ?
C3 F2 1.429(3) 8_565 ?
C3 C4 1.494(4) . ?
C3 C4 1.494(4) 8_565 ?
C3 C2 1.508(4) 8_565 ?
C4 C5 1.531(11) . ?
C8 C7 1.32(2) . ?
C8 C9 1.407(18) . ?
C9 C10 1.373(9) . ?
C10 C11 1.367(11) . ?
C11 C12 1.383(16) . ?
C12 C7 1.434(19) . ?
C7 C8 1.32(2) 8_565 ?
C7 C12 1.434(19) 8_565 ?
C7 S1 1.797(3) 8_565 ?

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
C1 N1 C5 123.9(6) . . ?
C1 N1 C6 115.9(6) . . ?
C5 N1 C6 115.7(3) . . ?
O1 C1 N1 123.0(4) . . ?
O1 C1 C2 118.7(3) . . ?
N1 C1 C2 117.6(3) . . ?
C2 S1 C7 99.31(13) . . ?
F1 C2 C3 103.1(2) . . ?
F1 C2 C1 103.5(5) . . ?
C3 C2 C1 115.5(3) . . ?
F1 C2 S1 110.0(2) . . ?
C3 C2 S1 115.9(2) . . ?
C1 C2 S1 108.0(3) . . ?
F2 C3 F2 176.6(3) 8_565 . ?
F2 C3 C4 68.87(19) 8_565 . ?
F2 C3 C4 108.2(2) . . ?
F2 C3 C4 108.2(2) 8_565 8_565 ?
F2 C3 C4 68.87(19) . 8_565 ?
C4 C3 C4 39.4(3) . 8_565 ?
F2 C3 C2 106.3(2) 8_565 8_565 ?
F2 C3 C2 76.58(17) . 8_565 ?
C4 C3 C2 121.9(2) . 8_565 ?
C4 C3 C2 110.8(2) 8_565 8_565 ?
F2 C3 C2 76.58(17) 8_565 . ?
F2 C3 C2 106.3(2) . . ?
C4 C3 C2 110.8(2) . . ?
C4 C3 C2 121.9(2) 8_565 . ?
C2 C3 C2 29.8(2) 8_565 . ?
C3 C4 C5 110.0(5) . . ?
N1 C5 C4 114.8(7) . . ?
C7 C8 C9 122.1(13) . . ?
C10 C9 C8 118.1(11) . . ?
C11 C10 C9 120.6(6) . . ?
C10 C11 C12 121.7(10) . . ?
C11 C12 C7 117.2(12) . . ?
C8 C7 C8 132.7(15) 8_565 . ?
C8 C7 C12 16.3(10) 8_565 . ?
C8 C7 C12 120.3(4) . . ?
C8 C7 C12 120.3(4) 8_565 8_565 ?
C8 C7 C12 16.3(10) . 8_565 ?
C12 C7 C12 106.1(11) . 8_565 ?
C8 C7 S1 123.8(6) 8_565 8_565 ?
C8 C7 S1 101.7(6) . 8_565 ?
C12 C7 S1 138.0(6) . 8_565 ?
C12 C7 S1 115.7(6) 8_565 8_565 ?
C8 C7 S1 101.7(6) 8_565 . ?
C8 C7 S1 123.8(6) . . ?
C12 C7 S1 115.7(6) . . ?
C12 C7 S1 138.0(6) 8_565 . ?
S1 C7 S1 22.28(7) 8_565 . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.054