#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/83/2208375.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208375
loop_
_publ_author_name
'Michael P. Hudock'
'Rong Cao'
'Yonghui Zhang'
'Wilson, Scott R.'
'Eric Oldfield'
_publ_section_title
;
 [2-(3-Fluoropyridinium-1-yl)-1-hydroxy-1-phosphonoethyl]phosphonate
;
_journal_coeditor_code           LH6584
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1003
_journal_page_last               o1005
_journal_paper_doi               10.1107/S1600536806004387
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H10 F N O7 P2'
_chemical_formula_moiety         'C7 H10 F N O7 P2'
_chemical_formula_sum            'C7 H10 F N O7 P2'
_chemical_formula_weight         301.10
_chemical_name_common
;
1-Hydroxy-2-[3-fluoropyridinium-1-yl]ethylidene-1,1-bisphosphonate
;
_chemical_name_systematic
;
[2-(3-Fluoropyridinium-1-yl)--1-hydroxy-1-phosphonoethyl]phosphonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.667(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1892(10)
_cell_length_b                   19.1693(4)
_cell_length_c                   9.3312(10)
_cell_measurement_reflns_used    4398
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.89
_cell_measurement_theta_min      3.05
_cell_volume                     1104.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Kappa-APEXII CCD'
_diffrn_measurement_method       'profile data from φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15680
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  785
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(SHELXTL/XPREP; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.6018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2665
_reflns_number_total             3201
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6584.cif
_cod_data_source_block           I
_cod_original_cell_volume        1104.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208375
_cod_database_fobs_code          2208375
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'
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
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_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'
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
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9441593
