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


data_global
_journal_coden_Cambridge              182
_publ_requested_journal               ' ChemComm'

loop_
_publ_author_name
'Percy, J.'
'Butt, Afshan H.'
'Kariuki, B. M.'
'Spencer, Neil S.'

_publ_contact_author                  'Dr. J.M. Percy'
_publ_contact_author_address
;
Dr. J.M. Percy 
Department of Chemistry, 
University of Leicester,
Universuty Road, 
Leicester, LE1 7RE
UK
;
_publ_contact_author_email            'jmp29@le.ac.uk'


_publ_section_title
;
Towards Stable Analogues of Inositol Phosphates: Stereoselective Synthesis 
of (a,a-Difluoromethyl)phophonic acid (DFMPA)-contsining Cyclohexanes
;

_publ_section_references
;
SHELXL-97, Program for Crystal Structure Determination
George M. Sheldrick, University of Gotingen, 1997.  

Molecular Structure Corporation. (1995). teXsan. 
Single Crystal Structure Analysis Software. Version 1.7.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564.
;

data_ahb2

_database_code_CSD	178066


_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H23 F2 O6 P S'
_chemical_formula_sum
'C17 H23 F2 O6 P S'
_chemical_formula_weight          424.38

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'
'S'  'S'   0.1246   0.1234
'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                    9.9968(6)
_cell_length_b                    16.8039(14)
_cell_length_c                    12.5119(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  104.776(2)
_cell_angle_gamma                 90.00
_cell_volume                      2032.3(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2947
_cell_measurement_theta_min       1.68
_cell_measurement_theta_max       25.21

_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.30
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.387
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              888
_exptl_absorpt_coefficient_mu     0.285
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.8705
_exptl_absorpt_correction_T_max   0.9193
_exptl_absorpt_process_details    ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Rigaku R-axis IIc'
_diffrn_measurement_method        'Image plate scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11831
_diffrn_reflns_av_R_equivalents   0.0364
_diffrn_reflns_av_sigmaI/netI     0.0377
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.68
_diffrn_reflns_theta_max          25.21
_reflns_number_total              3531
_reflns_number_gt                 2947
_reflns_threshold_expression      >2sigma(I)


_computing_data_collection        'MSC/AFC Diffractometer Control'
_computing_cell_refinement        'MSC/AFC Diffractometer Control'
_computing_data_reduction         'teXsan (MSC, 1995)'
_computing_structure_solution     'SIR92 (Altomare, et. al. 1993)' 
_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^)+(0.0710P)^2^+1.3904P] 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        0.021(10)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3531
_refine_ls_number_parameters      250
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0715
_refine_ls_R_factor_gt            0.0608
_refine_ls_wR_factor_ref          0.1572
_refine_ls_wR_factor_gt           0.1498
_refine_ls_goodness_of_fit_ref    1.003
_refine_ls_restrained_S_all       1.003
_refine_ls_shift/su_max           0.052
_refine_ls_shift/su_mean          0.007

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 -0.04342(7) 0.05707(4) 0.77192(6) 0.0568(3) Uani 1 1 d . . .
P1 P 0.34311(9) -0.04982(7) 0.67386(8) 0.0783(4) Uani 1 1 d . . .
F1 F 0.1712(2) -0.16735(11) 0.66906(19) 0.0943(7) Uani 1 1 d . . .
F2 F 0.3308(3) -0.15312(14) 0.82252(19) 0.1073(8) Uani 1 1 d . . .
O1 O -0.1060(3) -0.10822(14) 0.55291(17) 0.0796(7) Uani 1 1 d D . .
H18 H -0.155(4) -0.0655(16) 0.501(2) 0.096 Uiso 1 1 d D . .
O2 O -0.1437(2) 0.09662(14) 0.6860(2) 0.0864(8) Uani 1 1 d . . .
O3 O -0.0841(2) 0.03265(15) 0.86994(19) 0.0771(7) Uani 1 1 d . . .
O4 O 0.2587(3) 0.0003(2) 0.5887(2) 0.1096(10) Uani 1 1 d . . .
O5 O 0.4434(3) -0.1082(2) 0.6372(2) 0.1123(11) Uani 1 1 d . . .
O6 O 0.4325(3) -0.0064(3) 0.7765(3) 0.1390(15) Uani 1 1 d . . .
C1 C 0.0175(3) -0.02829(14) 0.7115(2) 0.0454(6) Uani 1 1 d . . .
H1 H 0.0545 -0.0092 0.6508 0.054 Uiso 1 1 calc R . .
C2 C 0.1375(3) -0.06845(14) 0.7970(2) 0.0487(6) Uani 1 1 d . . .
H2 H 0.1904 -0.0254 0.8412 0.058 Uiso 1 1 calc R . .
C3 C 0.0871(4) -0.12209(19) 0.8783(2) 0.0693(8) Uani 1 1 d . . .
H3A H 0.1608 -0.1584 0.9128 0.083 Uiso 1 1 calc R . .
H3B H 0.0671 -0.0892 0.9361 0.083 Uiso 1 1 calc R . .
C4 C -0.0379(4) -0.1688(2) 0.8255(3) 0.0865(11) Uani 1 1 d . . .
H4 H -0.0578 -0.2131 0.8632 0.104 Uiso 1 1 calc R . .
C5 C -0.1221(4) -0.1524(2) 0.7298(3) 0.0834(11) Uani 1 1 d . . .
H5 H -0.1954 -0.1871 0.7030 0.100 Uiso 1 1 calc R . .
C6 C -0.1096(3) -0.08197(17) 0.6602(2) 0.0589(7) Uani 1 1 d . . .
H6 H -0.1931 -0.0495 0.6523 0.071 Uiso 1 1 calc R . .
C7 C 0.1018(3) 0.12083(15) 0.8127(2) 0.0565(7) Uani 1 1 d . . .
C8 C 0.1426(4) 0.16571(17) 0.7345(3) 0.0787(10) Uani 1 1 d . . .
H8 H 0.0973 0.1610 0.6600 0.094 Uiso 1 1 calc R . .
C9 C 0.2530(5) 0.2183(2) 0.7690(4) 0.1030(14) Uani 1 1 d . . .
H9 H 0.2821 0.2492 0.7175 0.124 Uiso 1 1 calc R . .
C10 C 0.3187(5) 0.2243(2) 0.8792(5) 0.1069(14) Uani 1 1 d . . .
H10 H 0.3919 0.2598 0.9019 0.128 Uiso 1 1 calc R . .
C11 C 0.2786(4) 0.1793(2) 0.9559(4) 0.0918(12) Uani 1 1 d . . .
H11 H 0.3247 0.1838 1.0302 0.110 Uiso 1 1 calc R . .
C12 C 0.1692(3) 0.12669(19) 0.9235(3) 0.0684(8) Uani 1 1 d . . .
H12 H 0.1414 0.0957 0.9756 0.082 Uiso 1 1 calc R . .
C13 C 0.2374(3) -0.11126(17) 0.7424(2) 0.0619(8) Uani 1 1 d . . .
C14 C 0.4096(6) -0.1504(6) 0.5297(4) 0.189(4) Uani 1 1 d . . .
H14A H 0.3614 -0.1992 0.5380 0.226 Uiso 1 1 calc R . .
H14B H 0.3459 -0.1176 0.4762 0.226 Uiso 1 1 calc R . .
C15 C 0.5121(6) -0.1683(4) 0.4897(5) 0.147(2) Uani 1 1 d . . .
H15A H 0.4783 -0.1936 0.4192 0.176 Uiso 1 1 calc R . .
H15B H 0.5732 -0.2039 0.5392 0.176 Uiso 1 1 calc R . .
H15C H 0.5612 -0.1206 0.4808 0.176 Uiso 1 1 calc R . .
C16 C 0.5569(6) 0.0275(5) 0.7964(4) 0.170(3) Uani 1 1 d . . .
H16A H 0.5566 0.0653 0.7378 0.203 Uiso 1 1 calc R . .
H16B H 0.6244 -0.0133 0.7932 0.203 Uiso 1 1 calc R . .
C17 C 0.6003(5) 0.0673(5) 0.8986(5) 0.154(3) Uani 1 1 d . . .
H17A H 0.6815 0.0981 0.8998 0.184 Uiso 1 1 calc R . .
H17B H 0.6211 0.0289 0.9574 0.184 Uiso 1 1 calc R . .
H17C H 0.5279 0.1019 0.9082 0.184 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 0.0463(4) 0.0516(4) 0.0684(5) -0.0143(3) 0.0071(3) 0.0056(3)
P1 0.0603(5) 0.1023(7) 0.0757(6) -0.0135(5) 0.0234(4) 0.0048(5)
F1 0.0991(15) 0.0664(11) 0.1161(16) -0.0450(11) 0.0249(13) 0.0003(10)
F2 0.1158(17) 0.0973(15) 0.0989(15) 0.0207(12) 0.0090(13) 0.0648(14)
O1 0.0963(17) 0.0747(15) 0.0590(13) -0.0215(11) 0.0036(12) -0.0062(12)
O2 0.0691(14) 0.0717(14) 0.0995(17) -0.0144(12) -0.0132(13) 0.0272(11)
O3 0.0668(13) 0.0962(16) 0.0774(14) -0.0247(12) 0.0350(11) -0.0114(12)
O4 0.120(2) 0.125(2) 0.0991(19) 0.0424(17) 0.0562(18) 0.0315(19)
O5 0.0715(16) 0.183(3) 0.0798(17) -0.0322(18) 0.0151(13) 0.0392(18)
O6 0.0809(19) 0.202(4) 0.145(3) -0.089(3) 0.0484(19) -0.058(2)
C1 0.0461(13) 0.0395(12) 0.0480(13) -0.0036(10) 0.0074(11) -0.0008(10)
C2 0.0533(14) 0.0385(12) 0.0497(14) -0.0030(10) 0.0045(11) 0.0014(10)
C3 0.088(2) 0.0591(17) 0.0559(16) 0.0068(14) 0.0097(15) -0.0092(15)
C4 0.120(3) 0.0618(19) 0.073(2) 0.0071(16) 0.016(2) -0.036(2)
C5 0.090(2) 0.072(2) 0.082(2) -0.0079(18) 0.0113(19) -0.0417(19)
C6 0.0574(16) 0.0572(16) 0.0563(16) -0.0118(13) 0.0036(13) -0.0085(13)
C7 0.0594(16) 0.0355(12) 0.0714(18) -0.0089(12) 0.0111(13) 0.0038(11)
C8 0.104(3) 0.0451(15) 0.083(2) 0.0007(15) 0.016(2) -0.0055(16)
C9 0.131(4) 0.060(2) 0.123(4) 0.001(2) 0.041(3) -0.027(2)
C10 0.107(3) 0.075(2) 0.135(4) -0.025(3) 0.024(3) -0.040(2)
C11 0.091(3) 0.081(2) 0.095(3) -0.028(2) 0.008(2) -0.024(2)
C12 0.0686(19) 0.0621(17) 0.0715(19) -0.0197(15) 0.0126(15) -0.0072(14)
C13 0.0645(17) 0.0496(15) 0.0630(17) -0.0053(13) 0.0008(14) 0.0168(13)
C14 0.106(4) 0.354(11) 0.093(3) -0.083(5) 0.003(3) 0.079(5)
C15 0.132(5) 0.202(6) 0.112(4) -0.052(4) 0.042(4) -0.011(4)
C16 0.090(3) 0.323(10) 0.099(3) -0.051(5) 0.030(3) -0.085(5)
C17 0.075(3) 0.237(7) 0.146(5) -0.068(5) 0.023(3) -0.029(4)

_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 O2 1.433(2) . ?
S1 O3 1.447(2) . ?
S1 C7 1.772(3) . ?
S1 C1 1.798(2) . ?
P1 O4 1.448(3) . ?
P1 O6 1.548(3) . ?
P1 O5 1.554(3) . ?
P1 C13 1.838(3) . ?
F1 C13 1.363(3) . ?
F2 C13 1.376(3) . ?
O1 C6 1.422(3) . ?
O5 C14 1.482(6) . ?
O6 C16 1.332(5) . ?
C1 C2 1.544(3) . ?
C1 C6 1.557(3) . ?
C2 C13 1.527(4) . ?
C2 C3 1.537(4) . ?
C3 C4 1.481(5) . ?
C4 C5 1.305(5) . ?
C5 C6 1.493(5) . ?
C7 C8 1.377(5) . ?
C7 C12 1.381(4) . ?
C8 C9 1.394(5) . ?
C9 C10 1.371(6) . ?
C10 C11 1.360(6) . ?
C11 C12 1.384(5) . ?
C14 C15 1.285(7) . ?
C16 C17 1.409(7) . ?

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
O2 S1 O3 118.24(15) . . ?
O2 S1 C7 107.53(14) . . ?
O3 S1 C7 108.31(14) . . ?
O2 S1 C1 107.58(13) . . ?
O3 S1 C1 109.18(13) . . ?
C7 S1 C1 105.25(12) . . ?
O4 P1 O6 116.2(3) . . ?
O4 P1 O5 116.68(16) . . ?
O6 P1 O5 105.28(18) . . ?
O4 P1 C13 111.91(16) . . ?
O6 P1 C13 99.03(17) . . ?
O5 P1 C13 105.89(18) . . ?
C14 O5 P1 123.7(3) . . ?
C16 O6 P1 132.1(3) . . ?
C2 C1 C6 116.2(2) . . ?
C2 C1 S1 110.13(16) . . ?
C6 C1 S1 107.91(18) . . ?
C13 C2 C3 112.5(2) . . ?
C13 C2 C1 112.2(2) . . ?
C3 C2 C1 112.7(2) . . ?
C4 C3 C2 113.4(3) . . ?
C5 C4 C3 124.8(3) . . ?
C4 C5 C6 124.9(3) . . ?
O1 C6 C5 109.3(2) . . ?
O1 C6 C1 110.8(2) . . ?
C5 C6 C1 113.5(2) . . ?
C8 C7 C12 121.2(3) . . ?
C8 C7 S1 119.7(2) . . ?
C12 C7 S1 119.1(2) . . ?
C7 C8 C9 118.8(4) . . ?
C10 C9 C8 119.8(4) . . ?
C11 C10 C9 121.1(4) . . ?
C10 C11 C12 120.1(4) . . ?
C7 C12 C11 119.1(3) . . ?
F1 C13 F2 105.0(2) . . ?
F1 C13 C2 111.5(2) . . ?
F2 C13 C2 108.3(2) . . ?
F1 C13 P1 108.2(2) . . ?
F2 C13 P1 105.3(2) . . ?
C2 C13 P1 117.62(19) . . ?
C15 C14 O5 116.4(5) . . ?
O6 C16 C17 115.4(5) . . ?

_diffrn_measured_fraction_theta_max    0.966
_diffrn_reflns_theta_full              25.21
_diffrn_measured_fraction_theta_full   0.966
_refine_diff_density_max    0.471
_refine_diff_density_min   -0.434
_refine_diff_density_rms    0.042