# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003
data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
T.Lequeux
'A. Henry-dit-Quesnel'
'J. C. Pommelet'
'L. Toupet'

_publ_contact_author_name        'Dr Thierry Lequeux'
_publ_contact_author_address     
;
LCMT-UMR 6507
University - ENSICaen
6 Bd du Marechal Juin
Caen
14050
FRANCE
;

_publ_contact_author_email       THIERRY.LEQUEUX@ISMRA.FR

_publ_section_title              
;
A Difluorosulfide as a Freon-free Source of
Phosphonodifluoromethyl Carbanion
;

data_ah
_database_code_CSD               203879

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H17 F2 O5 P'
_chemical_formula_weight         262.19

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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/a

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

_cell_length_a                   6.751(2)
_cell_length_b                   24.363(9)
_cell_length_c                   8.0910(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.75(2)
_cell_angle_gamma                90.00
_cell_volume                     1302.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3072
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         26.96
_reflns_number_total             2837
_reflns_number_gt                2167
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0760P)^2^+0.3270P] 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       0.0000(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2837
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          2.780
_refine_ls_shift/su_mean         0.019

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
P1 P -0.04327(8) 0.37278(2) 0.20690(7) 0.04234(19) Uani 1 1 d . . .
F1 F 0.2509(2) 0.38817(7) 0.4679(2) 0.0716(5) Uani 1 1 d . . .
F2 F 0.3448(2) 0.39059(6) 0.2253(2) 0.0683(4) Uani 1 1 d . . .
O1 O -0.0653(3) 0.43413(6) 0.2538(3) 0.0654(5) Uani 1 1 d . . .
O2 O -0.0504(3) 0.37278(7) 0.0154(2) 0.0614(5) Uani 1 1 d . . .
O3 O -0.1769(2) 0.33277(6) 0.2650(2) 0.0487(4) Uani 1 1 d . . .
O4 O 0.5012(2) 0.30221(7) 0.4216(2) 0.0526(4) Uani 1 1 d . . .
H44 H 0.5855 0.3215 0.3474 0.050 Uiso 1 1 d . . .
O5 O 0.2559(2) 0.27959(6) 0.18484(19) 0.0511(4) Uani 1 1 d . . .
H55 H 0.2705 0.2405 0.2046 0.050 Uiso 1 1 d . . .
C1 C -0.2544(4) 0.46470(10) 0.2205(4) 0.0719(8) Uani 1 1 d . . .
H1 H -0.3601 0.4421 0.1516 0.086 Uiso 1 1 calc R . .
C2 C -0.2228(8) 0.51413(18) 0.1244(8) 0.161(3) Uani 1 1 d . . .
H2A H -0.1877 0.5035 0.0198 0.193 Uiso 1 1 calc R . .
H2B H -0.1153 0.5356 0.1892 0.193 Uiso 1 1 calc R . .
H2C H -0.3449 0.5355 0.1016 0.193 Uiso 1 1 calc R . .
C3 C -0.3110(7) 0.4765(2) 0.3829(7) 0.146(2) Uani 1 1 d . . .
H3A H -0.3303 0.4427 0.4383 0.175 Uiso 1 1 calc R . .
H3B H -0.4343 0.4973 0.3637 0.175 Uiso 1 1 calc R . .
H3C H -0.2052 0.4973 0.4529 0.175 Uiso 1 1 calc R . .
C4 C -0.1382(5) 0.32866(12) -0.1020(3) 0.0685(7) Uani 1 1 d . . .
H4 H -0.1192 0.2935 -0.0420 0.082 Uiso 1 1 calc R . .
C5 C -0.3604(6) 0.3391(2) -0.1587(5) 0.1258(17) Uani 1 1 d . . .
H5A H -0.4237 0.3388 -0.0627 0.151 Uiso 1 1 calc R . .
H5B H -0.4191 0.3110 -0.2366 0.151 Uiso 1 1 calc R . .
H5C H -0.3808 0.3743 -0.2132 0.151 Uiso 1 1 calc R . .
C6 C -0.0197(7) 0.32796(19) -0.2395(5) 0.1095(13) Uani 1 1 d . . .
H6A H 0.1202 0.3210 -0.1917 0.131 Uiso 1 1 calc R . .
H6B H -0.0325 0.3628 -0.2959 0.131 Uiso 1 1 calc R . .
H6C H -0.0709 0.2996 -0.3191 0.131 Uiso 1 1 calc R . .
C7 C 0.2241(3) 0.36318(8) 0.3141(3) 0.0432(5) Uani 1 1 d . . .
C8 C 0.2972(3) 0.30431(8) 0.3424(2) 0.0405(4) Uani 1 1 d . . .
H8 H 0.2175 0.2860 0.4147 0.049 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
P1 0.0361(3) 0.0343(3) 0.0562(3) -0.0002(2) 0.0082(2) -0.00020(19)
F1 0.0639(9) 0.0701(9) 0.0736(10) -0.0350(7) -0.0029(7) 0.0079(7)
F2 0.0445(7) 0.0552(8) 0.1080(12) 0.0195(8) 0.0221(7) -0.0091(6)
O1 0.0490(9) 0.0375(9) 0.1074(15) -0.0088(8) 0.0100(9) 0.0046(7)
O2 0.0705(11) 0.0568(10) 0.0531(9) 0.0105(7) 0.0032(8) -0.0135(8)
O3 0.0375(7) 0.0451(8) 0.0659(10) -0.0019(7) 0.0160(7) -0.0030(6)
O4 0.0368(7) 0.0628(10) 0.0571(9) 0.0033(7) 0.0071(7) 0.0033(7)
O5 0.0607(9) 0.0410(8) 0.0506(9) -0.0065(6) 0.0088(7) 0.0050(7)
C1 0.0500(14) 0.0433(12) 0.123(2) -0.0030(14) 0.0196(14) 0.0083(10)
C2 0.106(3) 0.086(3) 0.282(8) 0.082(4) 0.018(4) 0.014(2)
C3 0.100(3) 0.153(4) 0.200(5) -0.103(4) 0.069(3) -0.025(3)
C4 0.0791(18) 0.0726(17) 0.0495(13) -0.0026(12) 0.0032(13) -0.0111(14)
C5 0.083(3) 0.196(5) 0.085(3) -0.028(3) -0.016(2) -0.007(3)
C6 0.139(4) 0.123(3) 0.076(2) -0.013(2) 0.043(2) -0.020(3)
C7 0.0365(9) 0.0404(10) 0.0531(11) -0.0071(8) 0.0106(8) -0.0041(8)
C8 0.0357(9) 0.0428(10) 0.0440(10) -0.0004(8) 0.0101(8) -0.0001(8)

_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
P1 O3 1.4688(15) . ?
P1 O2 1.5405(18) . ?
P1 O1 1.5567(17) . ?
P1 C7 1.851(2) . ?
F1 C7 1.364(2) . ?
F2 C7 1.366(2) . ?
O1 C1 1.455(3) . ?
O2 C4 1.476(3) . ?
O4 C8 1.397(2) . ?
O4 H44 1.0215 . ?
O5 C8 1.386(2) . ?
O5 H55 0.9673 . ?
C1 C3 1.470(5) . ?
C1 C2 1.472(5) . ?
C1 H1 0.9800 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C6 1.497(4) . ?
C4 C5 1.498(5) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.519(3) . ?
C8 H8 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 P1 O2 115.25(10) . . ?
O3 P1 O1 117.63(10) . . ?
O2 P1 O1 105.09(10) . . ?
O3 P1 C7 111.71(10) . . ?
O2 P1 C7 107.41(10) . . ?
O1 P1 C7 98.01(9) . . ?
C1 O1 P1 124.74(16) . . ?
C4 O2 P1 124.98(16) . . ?
C8 O4 H44 109.2 . . ?
C8 O5 H55 106.3 . . ?
O1 C1 C3 108.2(3) . . ?
O1 C1 C2 107.5(3) . . ?
C3 C1 C2 113.8(4) . . ?
O1 C1 H1 109.1 . . ?
C3 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
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 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C6 106.3(3) . . ?
O2 C4 C5 108.6(3) . . ?
C6 C4 C5 115.3(3) . . ?
O2 C4 H4 108.8 . . ?
C6 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F1 C7 F2 106.21(17) . . ?
F1 C7 C8 107.79(18) . . ?
F2 C7 C8 109.32(16) . . ?
F1 C7 P1 107.84(14) . . ?
F2 C7 P1 108.73(15) . . ?
C8 C7 P1 116.46(14) . . ?
O5 C8 O4 113.62(16) . . ?
O5 C8 C7 105.88(16) . . ?
O4 C8 C7 111.30(17) . . ?
O5 C8 H8 108.6 . . ?
O4 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?

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 P1 O1 C1 -53.0(3) . . . . ?
O2 P1 O1 C1 76.8(2) . . . . ?
C7 P1 O1 C1 -172.7(2) . . . . ?
O3 P1 O2 C4 -15.5(2) . . . . ?
O1 P1 O2 C4 -146.7(2) . . . . ?
C7 P1 O2 C4 109.7(2) . . . . ?
P1 O1 C1 C3 111.3(3) . . . . ?
P1 O1 C1 C2 -125.4(3) . . . . ?
P1 O2 C4 C6 -149.1(3) . . . . ?
P1 O2 C4 C5 86.3(3) . . . . ?
O3 P1 C7 F1 -81.33(16) . . . . ?
O2 P1 C7 F1 151.37(14) . . . . ?
O1 P1 C7 F1 42.73(17) . . . . ?
O3 P1 C7 F2 163.91(13) . . . . ?
O2 P1 C7 F2 36.61(16) . . . . ?
O1 P1 C7 F2 -72.03(16) . . . . ?
O3 P1 C7 C8 39.92(18) . . . . ?
O2 P1 C7 C8 -87.38(16) . . . . ?
O1 P1 C7 C8 163.98(16) . . . . ?
F1 C7 C8 O5 176.43(16) . . . . ?
F2 C7 C8 O5 -68.5(2) . . . . ?
P1 C7 C8 O5 55.2(2) . . . . ?
F1 C7 C8 O4 -59.7(2) . . . . ?
F2 C7 C8 O4 55.4(2) . . . . ?
P1 C7 C8 O4 179.06(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.96
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.049