##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[2-(3-Fluoropyridinium-1-yl)--1-hydroxy-1-phosphonoethyl]phosphonate
;
_chemical_name_common
;
1-Hydroxy-2-[3-fluoropyridinium-1-yl]ethylidene-1,1-bisphosphonate
;
_chemical_formula_moiety     'C7 H10 F N O7 P2'
_chemical_formula_sum     'C7 H10 F N O7 P2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C7 H10 F N O7 P2'
_chemical_formula_weight     301.10
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.1892(10)
_cell_length_b     19.1693(4)
_cell_length_c     9.3312(10)
_cell_angle_alpha     90.00
_cell_angle_beta     93.667(10)
_cell_angle_gamma     90.00
_cell_volume     1104.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4398
_cell_measurement_theta_min     3.05
_cell_measurement_theta_max     29.89
_cell_measurement_temperature     193(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.10
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.810
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    1.00 0.00 0.00 0.1200
    -1.00 0.00 0.00 0.1200
    0.00 0.00 1.00 0.0150
    0.00 0.00 -1.00 0.0150
    1.00 -1.00 0.00 0.2300
    0.00 1.00 0.00 0.4000
    -1.00 -1.00 0.00 0.2800
_exptl_absorpt_coefficient_mu     0.436
_exptl_absorpt_correction_type     'integration'
_exptl_absorpt_process_details     '(SHELXTL/XPREP; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.9674
_exptl_absorpt_correction_T_max     0.9805
_exptl_special_details
;
The crystal was mounted using oil (Parantone-N, Exxon) to a 0.3 mm
cryo-loop (Hampton Research) with the (0 1 1) scattering planes
roughly normal to the spindle axis.
One distinct cell was identified using SMART (Bruker, 2001).  Four
frame series were integrated and filtered for statistical outliers
using SAINT (Bruker, 2001) then corrected for absorption by
integration using SHELXTL/XPREP (Bruker, 2001) before using
SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined
data.  A series of identical frames was collected twice during the
experiment to monitor decay.  No decay correction was applied.
;
_diffrn_ambient_temperature     193(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Bruker Kappa-APEXII CCD'
_diffrn_measurement_method     'profile data from φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15680
_diffrn_reflns_av_R_equivalents     0.0319
_diffrn_reflns_av_sigmaI/netI     0.0247
_diffrn_reflns_theta_min     2.12
_diffrn_reflns_theta_max     29.96
_diffrn_reflns_theta_full     29.96
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     785
_diffrn_standards_decay_%     0
_refine_special_details
;
Structure was phased by direct methods.  Systematic conditions suggested
the unambiguous space group.  The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F².  The highest peaks in the final difference Fourier map were in the
vicinity of atoms O8 and C1; the final map had no other significant
features.  A final analysis of variance between observed and calculated
structure factors showed little dependence on amplitude or resolution.
;
_reflns_number_total     3201
_reflns_number_gt     2665
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0423
_refine_ls_R_factor_gt     0.0325
_refine_ls_wR_factor_gt     0.0814
_refine_ls_wR_factor_ref     0.0876
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     3201
_refine_ls_number_parameters     176
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0429P)²+0.6018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.503
_refine_diff_density_min     -0.320
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Bruker, 2001)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'XCIF (Bruker, 2001)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.41226(6) 0.44840(2) 0.79354(4) 0.01326(9) Uani d . 1 . .
    P P2 0.76404(6) 0.553024(19) 0.72862(4) 0.01317(9) Uani d . 1 . .
    F F1 1.0442(3) 0.21499(7) 0.91950(17) 0.0600(4) Uani d . 1 . .
    O O1 0.39928(18) 0.38731(6) 0.90243(12) 0.0191(2) Uani d D 1 . .
    H H1 0.361(3) 0.3987(11) 0.9834(18) 0.029 Uiso d D 1 . .
    O O2 0.31637(16) 0.51504(6) 0.84706(11) 0.0167(2) Uani d . 1 . .
    O O3 0.31103(17) 0.42278(6) 0.65129(11) 0.0195(2) Uani d . 1 . .
    O O4 0.99640(17) 0.55301(6) 0.67293(12) 0.0171(2) Uani d D 1 . .
    H H2 1.095(3) 0.5425(11) 0.735(2) 0.026 Uiso d D 1 . .
    O O5 0.60909(18) 0.57201(6) 0.59910(12) 0.0196(2) Uani d D 1 . .
    H H3 0.653(3) 0.5672(11) 0.5133(18) 0.029 Uiso d D 1 . .
    O O6 0.74308(18) 0.59889(6) 0.85500(11) 0.0197(2) Uani d . 1 . .
    O O7 0.83747(17) 0.44439(6) 0.90109(11) 0.0162(2) Uani d D 1 . .
    H H4 0.792(3) 0.4585(11) 0.9773(18) 0.024 Uiso d D 1 . .
    N N1 0.7718(2) 0.33893(7) 0.69094(14) 0.0173(2) Uani d . 1 . .
    C C1 0.7074(2) 0.46110(7) 0.77452(14) 0.0127(3) Uani d . 1 . .
    C C2 0.7916(2) 0.41441(7) 0.65544(15) 0.0151(3) Uani d . 1 . .
    H H5 0.7080 0.4242 0.5636 0.018 Uiso calc R 1 . .
    H H6 0.9453 0.4257 0.6428 0.018 Uiso calc R 1 . .
    C C3 0.9182(3) 0.31083(9) 0.78694(19) 0.0252(3) Uani d . 1 . .
    H H7 1.0328 0.3382 0.8298 0.030 Uiso calc R 1 . .
    C C4 0.8982(3) 0.24148(10) 0.8216(2) 0.0356(4) Uani d . 1 . .
    C C5 0.7353(4) 0.20018(10) 0.7608(3) 0.0440(5) Uani d . 1 . .
    H H8 0.7236 0.1524 0.7859 0.053 Uiso calc R 1 . .
    C C6 0.5903(3) 0.23074(10) 0.6623(3) 0.0414(5) Uani d . 1 . .
    H H9 0.4758 0.2039 0.6178 0.050 Uiso calc R 1 . .
    C C7 0.6104(3) 0.30032(9) 0.6277(2) 0.0288(4) Uani d . 1 . .
    H H10 0.5101 0.3211 0.5591 0.035 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    P1 0.01074(16) 0.01730(18) 0.01175(16) 0.00011(13) 0.00082(12) 0.00006(13)
    P2 0.01348(17) 0.01403(18) 0.01206(17) 0.00128(12) 0.00120(12) 0.00141(13)
    F1 0.0821(11) 0.0305(7) 0.0642(9) 0.0158(7) -0.0195(8) 0.0132(6)
    O1 0.0232(5) 0.0184(5) 0.0162(5) -0.0008(4) 0.0057(4) 0.0019(4)
    O2 0.0140(5) 0.0198(5) 0.0163(5) 0.0033(4) 0.0012(4) -0.0005(4)
    O3 0.0145(5) 0.0300(6) 0.0140(5) -0.0021(4) -0.0002(4) -0.0039(4)
    O4 0.0129(5) 0.0196(5) 0.0189(5) 0.0002(4) 0.0016(4) 0.0043(4)
    O5 0.0165(5) 0.0282(6) 0.0139(5) 0.0052(4) 0.0008(4) 0.0050(4)
    O6 0.0271(6) 0.0167(5) 0.0157(5) -0.0011(4) 0.0045(4) -0.0016(4)
    O7 0.0149(5) 0.0213(5) 0.0121(5) 0.0035(4) -0.0022(4) -0.0003(4)
    N1 0.0162(6) 0.0150(6) 0.0210(6) 0.0000(4) 0.0026(5) -0.0043(5)
    C1 0.0113(6) 0.0149(6) 0.0117(6) 0.0012(5) -0.0004(5) 0.0001(5)
    C2 0.0143(6) 0.0149(7) 0.0162(6) -0.0003(5) 0.0025(5) -0.0014(5)
    C3 0.0264(8) 0.0196(8) 0.0292(8) 0.0037(6) -0.0018(7) -0.0019(6)
    C4 0.0450(11) 0.0216(9) 0.0397(10) 0.0093(8) 0.0001(9) 0.0032(8)
    C5 0.0521(13) 0.0147(8) 0.0662(15) -0.0018(8) 0.0127(11) -0.0006(9)
    C6 0.0351(10) 0.0195(9) 0.0692(15) -0.0065(7) 0.0005(10) -0.0108(9)
    C7 0.0229(8) 0.0220(8) 0.0409(10) -0.0014(6) -0.0012(7) -0.0100(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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    P1 O2 . 1.5071(11) ?
    P1 O3 . 1.5130(11) ?
    P1 O1 . 1.5559(11) ?
    P1 C1 . 1.8625(14) ?
    P2 O6 . 1.4833(11) ?
    P2 O5 . 1.5377(11) ?
    P2 O4 . 1.5601(11) ?
    P2 C1 . 1.8522(15) ?
    F1 C4 . 1.343(2) ?
    O1 H1 . 0.834(15) ?
    O4 H2 . 0.840(15) ?
    O5 H3 . 0.867(15) ?
    O7 C1 . 1.4226(16) ?
    O7 H4 . 0.827(15) ?
    N1 C3 . 1.345(2) ?
    N1 C7 . 1.348(2) ?
    N1 C2 . 1.4911(19) ?
    C1 C2 . 1.5431(19) ?
    C2 H5 . 0.9900 ?
    C2 H6 . 0.9900 ?
    C3 C4 . 1.376(3) ?
    C3 H7 . 0.9500 ?
    C4 C5 . 1.376(3) ?
    C5 C6 . 1.374(3) ?
    C5 H8 . 0.9500 ?
    C6 C7 . 1.380(3) ?
    C6 H9 . 0.9500 ?
    C7 H10 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 P1 O3 . . 114.59(6) ?
    O2 P1 O1 . . 112.56(6) ?
    O3 P1 O1 . . 107.03(7) ?
    O2 P1 C1 . . 109.28(6) ?
    O3 P1 C1 . . 108.21(6) ?
    O1 P1 C1 . . 104.63(6) ?
    O6 P2 O5 . . 113.75(7) ?
    O6 P2 O4 . . 113.22(6) ?
    O5 P2 O4 . . 106.27(6) ?
    O6 P2 C1 . . 110.65(6) ?
    O5 P2 C1 . . 106.81(6) ?
    O4 P2 C1 . . 105.60(6) ?
    P1 O1 H1 . . 115.0(15) ?
    P2 O4 H2 . . 114.5(14) ?
    P2 O5 H3 . . 118.9(14) ?
    C1 O7 H4 . . 115.8(15) ?
    C3 N1 C7 . . 121.34(15) ?
    C3 N1 C2 . . 118.35(13) ?
    C7 N1 C2 . . 120.30(14) ?
    O7 C1 C2 . . 105.55(11) ?
    O7 C1 P2 . . 107.50(9) ?
    C2 C1 P2 . . 107.92(9) ?
    O7 C1 P1 . . 113.45(9) ?
    C2 C1 P1 . . 111.78(9) ?
    P2 C1 P1 . . 110.34(7) ?
    N1 C2 C1 . . 111.50(11) ?
    N1 C2 H5 . . 109.3 ?
    C1 C2 H5 . . 109.3 ?
    N1 C2 H6 . . 109.3 ?
    C1 C2 H6 . . 109.3 ?
    H5 C2 H6 . . 108.0 ?
    N1 C3 C4 . . 118.46(16) ?
    N1 C3 H7 . . 120.8 ?
    C4 C3 H7 . . 120.8 ?
    F1 C4 C5 . . 120.43(18) ?
    F1 C4 C3 . . 117.31(18) ?
    C5 C4 C3 . . 122.26(19) ?
    C6 C5 C4 . . 117.44(18) ?
    C6 C5 H8 . . 121.3 ?
    C4 C5 H8 . . 121.3 ?
    C5 C6 C7 . . 120.26(19) ?
    C5 C6 H9 . . 119.9 ?
    C7 C6 H9 . . 119.9 ?
    N1 C7 C6 . . 120.24(18) ?
    N1 C7 H10 . . 119.9 ?
    C6 C7 H10 . . 119.9 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O6 P2 C1 O7 . . . . -51.22(11) ?
    O5 P2 C1 O7 . . . . -175.51(9) ?
    O4 P2 C1 O7 . . . . 71.65(10) ?
    O6 P2 C1 C2 . . . . -164.63(9) ?
    O5 P2 C1 C2 . . . . 71.08(10) ?
    O4 P2 C1 C2 . . . . -41.76(10) ?
    O6 P2 C1 P1 . . . . 72.97(8) ?
    O5 P2 C1 P1 . . . . -51.32(8) ?
    O4 P2 C1 P1 . . . . -164.17(7) ?
    O2 P1 C1 O7 . . . . 89.89(11) ?
    O3 P1 C1 O7 . . . . -144.73(10) ?
    O1 P1 C1 O7 . . . . -30.87(11) ?
    O2 P1 C1 C2 . . . . -150.91(9) ?
    O3 P1 C1 C2 . . . . -25.52(12) ?
    O1 P1 C1 C2 . . . . 88.34(10) ?
    O2 P1 C1 P2 . . . . -30.81(9) ?
    O3 P1 C1 P2 . . . . 94.58(8) ?
    O1 P1 C1 P2 . . . . -151.56(7) ?
    C3 N1 C2 C1 . . . . -77.51(16) ?
    C7 N1 C2 C1 . . . . 102.50(16) ?
    O7 C1 C2 N1 . . . . 59.80(14) ?
    P2 C1 C2 N1 . . . . 174.51(9) ?
    P1 C1 C2 N1 . . . . -63.97(13) ?
    C7 N1 C3 C4 . . . . -1.0(2) ?
    C2 N1 C3 C4 . . . . 178.96(15) ?
    N1 C3 C4 F1 . . . . -178.88(17) ?
    N1 C3 C4 C5 . . . . 0.5(3) ?
    F1 C4 C5 C6 . . . . 179.4(2) ?
    C3 C4 C5 C6 . . . . 0.1(3) ?
    C4 C5 C6 C7 . . . . -0.1(3) ?
    C3 N1 C7 C6 . . . . 1.0(3) ?
    C2 N1 C7 C6 . . . . -179.02(17) ?
    C5 C6 C7 N1 . . . . -0.4(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O5 H3 O3 3_666 0.867(15) 1.577(16) 2.4209(15) 163(2)
    O1 H1 O6 3_667 0.834(15) 1.679(16) 2.4950(15) 165(2)
    O4 H2 O2 1_655 0.840(15) 1.749(15) 2.5846(15) 173(2)
    O7 H4 O2 3_667 0.827(15) 1.880(15) 2.7056(15) 177(2)
    C2 H5 O5 3_666 0.99 2.40 3.3326(17) 156
    C2 H6 O3 1_655 0.99 2.26 3.2216(16) 163
    C3 H7 O1 1_655 0.95 2.51 3.430(2) 164
    C5 H8 O4 2_746 0.95 2.59 3.312(2) 133
    C6 H9 O6 2_646 0.95 2.45 3.260(2) 143
data_global
_journal_date_recd_electronic     2006-01-17
_journal_date_accepted     2006-02-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      3
_journal_page_first     o1003
_journal_page_last     o1005
_journal_paper_category     EO
_journal_coeditor_code     LH6584
_publ_contact_author
;
Eric Oldfield
University of Illinois
Department of Chemistry
600 South Mathews Avenue
Urbana, Illinois  61801
USA
;
_publ_contact_author_email     eo@chad.scs.uiuc.edu
_publ_contact_author_fax     '1  217 244 0997'
_publ_contact_author_phone     '1  217 333 3374'
_publ_section_title
;
[2-(3-Fluoropyridinium-1-yl)-1-hydroxy-1-phosphonoethyl]phosphonate
;
loop_
    _publ_author_name
    _publ_author_address
    'Michael P. Hudock'
;
Center for Biophysics and Computational Biology
University of Illinois at Urbana-Champaign
607 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Rong Cao'
;
Center for Biophysics and Computational Biology
University of Illinois at Urbana-Champaign
607 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Yonghui Zhang'
;
Department of Chemistry
University of Illinois at Urbana-Champaign
600 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Wilson, Scott R.'
;
School of Chemical Sciences, Box 59-1
University of Illinois at Urbana-Champaign
505 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Eric Oldfield'
;
Department of Chemistry
University of Illinois at Urbana-Champaign
600 South Mathews Avenue
Urbana, Illinois 61801
USA
;
