#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012865.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012865
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o521
_journal_page_last  o524
_publ_section_title
;
[Hydroxy(aryl)methylene]diphosphonic acids, a class of drugs in bone
pathology treatments, crystallize as head-to-head dimers
;
loop_
_publ_author_name
  'Lecouvey, Marc'
  'Barbey, Carole'
  'Navaza, Alda'
  'Neuman, Alain'
  'Prang\'e, Thierry'
_chemical_formula_moiety  'C7 H10 O7 P2 , H2 O'
_chemical_formula_sum  'C7 H12 O8 P2'
_chemical_formula_iupac  'C7 H10 O7 P2 , H2 O'
_chemical_formula_weight  286.10
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  8.42(2)
_cell_length_b  23.050(10)
_cell_length_c  5.91(2)
_cell_angle_alpha  90
_cell_angle_beta  97.7(2)
_cell_angle_gamma  90
_cell_volume  1137(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.668
_diffrn_ambient_temperature  293(2)
loop_
_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
_atom_site_type_symbol
  P1 0.88450(15) 0.23466(5) 0.1837(2) 0.0269(3) Uani d . 1 . . P
  P2 0.65186(15) 0.14613(6) 0.3620(2) 0.0272(3) Uani d . 1 . . P
  O1 0.9098(4) 0.26948(16) 0.4003(5) 0.0320(8) Uani d . 1 . . O
  O2 1.0351(4) 0.23296(17) 0.0580(6) 0.0334(8) Uani d . 1 . . O
  H21 1.1103 0.2187 0.1421 0.040 Uiso calc R 1 . . H
  O3 0.7506(5) 0.25647(18) 0.0005(6) 0.0420(10) Uani d . 1 . . O
  H31 0.6982 0.2815 0.0555 0.063 Uiso calc R 1 . . H
  O4 0.6528(4) 0.17542(15) 0.5883(5) 0.0288(8) Uani d . 1 . . O
  O5 0.5164(5) 0.1659(2) 0.1736(6) 0.0465(11) Uani d . 1 . . O
  H51 0.4566 0.1885 0.2285 0.070 Uiso calc R 1 . . H
  O6 0.6335(5) 0.07893(17) 0.3700(6) 0.0374(9) Uani d . 1 . . O
  H61 0.6775 0.0667 0.4929 0.056 Uiso calc R 1 . . H
  O7 0.7989(4) 0.13214(17) 0.0088(5) 0.0327(9) Uani d . 1 . . O
  H71 0.7591 0.1563 -0.0836 0.049 Uiso calc R 1 . . H
  C1 0.8353(6) 0.1590(2) 0.2318(8) 0.0323(12) Uani d . 1 . . C
  C2 0.9771(6) 0.1303(2) 0.3644(9) 0.0326(13) Uani d . 1 . . C
  C3 1.0611(7) 0.0870(3) 0.2660(9) 0.0390(13) Uani d . 1 . . C
  H3 1.0239 0.0750 0.1182 0.047 Uiso calc R 1 . . H
  C4 1.1970(7) 0.0614(3) 0.3787(10) 0.0418(14) Uani d . 1 . . C
  H4 1.2486 0.0318 0.3106 0.050 Uiso calc R 1 . . H
  C5 1.2549(7) 0.0809(3) 0.5964(10) 0.0461(15) Uani d . 1 . . C
  H5 1.3503 0.0664 0.6733 0.055 Uiso calc R 1 . . H
  C6 1.1681(8) 0.1220(3) 0.6957(10) 0.0458(16) Uani d . 1 . . C
  H6 1.2022 0.1335 0.8451 0.055 Uiso calc R 1 . . H
  C7 1.0300(6) 0.1468(2) 0.5771(7) 0.0256(10) Uani d . 1 . . C
  H7 0.9747 0.1751 0.6472 0.031 Uiso calc R 1 . . H
  P1' 0.33318(16) 0.27646(6) 0.5223(2) 0.0270(3) Uani d . 1 . . P
  P2' 0.56673(14) 0.36521(6) 0.3454(2) 0.0255(3) Uani d . 1 . . P
  O1' 0.3137(4) 0.24395(16) 0.2966(6) 0.0296(8) Uani d . 1 . . O
  O2' 0.1883(4) 0.28018(16) 0.6471(6) 0.0339(8) Uani d . 1 . . O
  H2P 0.1078 0.2712 0.5602 0.051 Uiso calc R 1 . . H
  O3' 0.4617(5) 0.25226(14) 0.7047(6) 0.0283(9) Uani d . 1 . . O
  H3P 0.5102 0.2261 0.6498 0.042 Uiso calc R 1 . . H
  O4' 0.5634(4) 0.33683(15) 0.1205(6) 0.0297(8) Uani d . 1 . . O
  O5' 0.7042(4) 0.34501(17) 0.5285(6) 0.0389(10) Uani d . 1 . . O
  H5P 0.7652 0.3238 0.4693 0.058 Uiso calc R 1 . . H
  O6' 0.5784(5) 0.43272(16) 0.3357(7) 0.0422(10) Uani d . 1 . . O
  H6P 0.5467 0.4439 0.2058 0.063 Uiso calc R 1 . . H
  O7' 0.4147(4) 0.37970(13) 0.7040(5) 0.0245(7) Uani d . 1 . . O
  H72 0.4908 0.3632 0.7783 0.037 Uiso calc R 1 . . H
  C1' 0.3842(6) 0.3541(2) 0.4783(8) 0.0245(11) Uani d . 1 . . C
  C2' 0.2401(7) 0.3814(3) 0.3509(9) 0.0362(13) Uani d . 1 . . C
  C3' 0.1543(6) 0.4203(2) 0.4541(8) 0.0329(12) Uani d . 1 . . C
  H3' 0.1897 0.4323 0.6025 0.039 Uiso calc R 1 . . H
  C4' 0.0091(9) 0.4430(3) 0.3348(13) 0.0579(18) Uani d . 1 . . C
  H4' -0.0538 0.4678 0.4095 0.070 Uiso calc R 1 . . H
  C5' -0.0386(7) 0.4285(3) 0.1118(10) 0.0406(14) Uani d . 1 . . C
  H5' -0.1304 0.4451 0.0327 0.049 Uiso calc R 1 . . H
  C6' 0.0455(7) 0.3914(3) 0.0102(11) 0.0564(18) Uani d . 1 . . C
  H6' 0.0118 0.3814 -0.1411 0.068 Uiso calc R 1 . . H
  C7' 0.1827(7) 0.3667(3) 0.1220(11) 0.0430(15) Uani d . 1 . . C
  H7' 0.2388 0.3399 0.0459 0.052 Uiso calc R 1 . . H
  O1W 0.5302(6) 0.4803(2) -0.0653(8) 0.0599(12) Uani d . 1 . . O
  O2W 0.7012(7) 0.03416(19) 0.7769(8) 0.0656(14) Uani d . 1 . . O
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 0.0261(7) 0.0222(7) 0.0322(7) 0.0020(6) 0.0029(5) -0.0084(5)
  P2 0.0226(6) 0.0315(7) 0.0258(7) 0.0025(6) -0.0033(5) 0.0021(5)
  O1 0.036(2) 0.040(2) 0.0181(16) 0.0022(17) -0.0008(14) -0.0149(15)
  O2 0.0239(19) 0.045(2) 0.0328(18) -0.0047(17) 0.0080(15) 0.0003(17)
  O3 0.022(2) 0.056(3) 0.043(2) 0.0100(17) -0.0133(16) -0.0125(19)
  O4 0.0230(18) 0.038(2) 0.0227(18) 0.0040(15) -0.0065(13) -0.0074(15)
  O5 0.026(2) 0.087(3) 0.0228(19) 0.008(2) -0.0087(15) -0.017(2)
  O6 0.033(2) 0.038(2) 0.044(2) -0.0056(16) 0.0133(17) -0.0075(17)
  O7 0.0269(18) 0.057(3) 0.0140(16) 0.0097(17) 0.0018(13) -0.0069(15)
  C1 0.030(3) 0.035(3) 0.032(3) -0.010(2) 0.004(2) -0.003(2)
  C2 0.027(3) 0.030(3) 0.038(3) 0.002(2) -0.005(2) -0.009(2)
  C3 0.047(3) 0.039(3) 0.030(3) 0.011(3) -0.001(2) -0.001(2)
  C4 0.024(3) 0.046(4) 0.057(4) 0.013(3) 0.008(2) 0.014(3)
  C5 0.031(3) 0.060(4) 0.045(4) 0.012(3) -0.007(3) 0.014(3)
  C6 0.055(4) 0.050(4) 0.030(3) -0.017(3) -0.001(3) 0.009(3)
  C7 0.031(3) 0.026(3) 0.019(2) 0.002(2) 0.0019(19) -0.008(2)
  P1' 0.0285(7) 0.0323(8) 0.0185(7) 0.0031(6) -0.0027(5) 0.0043(5)
  P2' 0.0193(6) 0.0321(7) 0.0263(7) -0.0013(5) 0.0077(5) -0.0051(5)
  O1' 0.0196(18) 0.034(2) 0.0361(18) 0.0058(15) 0.0059(14) 0.0047(15)
  O2' 0.033(2) 0.025(2) 0.044(2) -0.0098(17) 0.0088(16) -0.0025(16)
  O3' 0.034(2) 0.0168(17) 0.0313(19) 0.0124(14) -0.0073(16) -0.0083(14)
  O4' 0.0299(19) 0.031(2) 0.029(2) 0.0086(16) 0.0080(14) 0.0056(15)
  O5' 0.024(2) 0.051(3) 0.043(2) 0.0096(18) 0.0058(16) -0.0036(18)
  O6' 0.046(2) 0.021(2) 0.059(3) -0.0104(17) 0.0074(19) 0.0088(17)
  O7' 0.0284(19) 0.0158(19) 0.0297(18) 0.0062(13) 0.0057(14) -0.0041(13)
  C1' 0.022(2) 0.027(3) 0.023(2) 0.007(2) -0.0018(18) 0.0024(19)
  C2' 0.041(3) 0.047(4) 0.022(3) 0.002(3) 0.011(2) 0.001(2)
  C3' 0.026(3) 0.047(3) 0.025(3) 0.001(2) 0.003(2) -0.001(2)
  C4' 0.068(5) 0.029(3) 0.080(5) 0.012(3) 0.022(4) 0.002(3)
  C5' 0.028(3) 0.045(4) 0.050(4) 0.002(2) 0.007(3) 0.018(3)
  C6' 0.035(4) 0.076(5) 0.054(4) 0.014(3) -0.010(3) -0.005(3)
  C7' 0.022(3) 0.041(3) 0.067(4) 0.013(3) 0.011(3) 0.017(3)
  O1W 0.065(3) 0.060(3) 0.055(3) -0.002(3) 0.007(2) 0.006(2)
  O2W 0.092(4) 0.033(3) 0.072(3) -0.006(3) 0.012(3) 0.000(2)
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 O1 . 1.502(6) yes
  P1 O2 . 1.554(5) yes
  P1 O3 . 1.539(6) yes
  P1 C1 . 1.824(5) yes
  P2 O4 . 1.497(7) yes
  P2 O5 . 1.552(6) yes
  P2 O6 . 1.558(4) yes
  P2 C1 . 1.840(7) yes
  O2 H21 . 0.8200 ?
  O3 H31 . 0.8200 ?
  O5 H51 . 0.8200 ?
  O6 H61 . 0.8201 ?
  O7 C1 . 1.451(8) ?
  O7 H71 . 0.8200 ?
  C1 C2 . 1.492(8) ?
  C2 C7 . 1.333(9) ?
  C2 C3 . 1.393(8) ?
  C3 C4 . 1.378(8) ?
  C3 H3 . 0.9300 ?
  C4 C5 . 1.388(10) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.376(10) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.397(8) ?
  C6 H6 . 0.9300 ?
  C7 H7 . 0.9300 ?
  P1' O1' . 1.520(7) yes
  P1' O2' . 1.511(5) yes
  P1' O3' . 1.527(6) yes
  P1' C1' . 1.866(5) yes
  P2' O4' . 1.478(7) yes
  P2' O5' . 1.547(6) yes
  P2' O6' . 1.561(4) yes
  P2' C1' . 1.836(7) yes
  O2' H2P . 0.8200 ?
  O3' H3P . 0.8200 ?
  O5' H5P . 0.8200 ?
  O6' H6P . 0.8200 ?
  O7' C1' . 1.450(8) ?
  O7' H72 . 0.8200 ?
  C1' C2' . 1.480(8) ?
  C2' C3' . 1.347(8) ?
  C2' C7' . 1.415(11) ?
  C3' C4' . 1.427(10) ?
  C3' H3' . 0.9300 ?
  C4' C5' . 1.366(11) ?
  C4' H4' . 0.9300 ?
  C5' C6' . 1.309(9) ?
  C5' H5' . 0.9300 ?
  C6' C7' . 1.374(8) ?
  C6' H6' . 0.9300 ?
  C7' H7' . 0.9300 ?