data_2012864
_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 H9 N O9 P2 , 2C4 H8 O'
_chemical_formula_sum  'C15 H25 N O11 P2'
_chemical_formula_iupac  'C7 H9 N O9 P2 , 2C4 H8 O'
_chemical_formula_weight  457.30
_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  14.0005(9)
_cell_length_b  6.0243(2)
_cell_length_c  24.4427(6)
_cell_angle_alpha  90
_cell_angle_beta  91.903(3)
_cell_angle_gamma  90
_cell_volume  2060.44(16)
_cell_formula_units_Z  4
_cell_measurement_temperature  132.0(10)
_exptl_crystal_density_diffrn  1.474
_diffrn_ambient_temperature  132.0(10)
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 0.55465(4) 0.66665(10) 0.58375(2) 0.01872(17) Uani d . 1 . . P
  O1 0.49584(12) 0.4582(3) 0.58560(7) 0.0245(4) Uani d . 1 . . O
  O2 0.56520(13) 0.7910(3) 0.63979(7) 0.0288(4) Uani d . 1 . . O
  H21 0.513(3) 0.808(6) 0.6577(14) 0.065(5) Uiso d . 1 . . H
  O3 0.51952(13) 0.8351(3) 0.53926(7) 0.0275(4) Uani d . 1 . . O
  H31 0.469(3) 0.814(6) 0.5242(14) 0.065(5) Uiso d . 1 . . H
  P2 0.70353(4) 0.45461(10) 0.50407(2) 0.01808(17) Uani d . 1 . . P
  O4 0.65329(11) 0.2339(3) 0.50446(6) 0.0209(4) Uani d . 1 . . O
  O5 0.67212(13) 0.6113(3) 0.45586(6) 0.0237(4) Uani d . 1 . . O
  H51 0.608(3) 0.589(6) 0.4440(14) 0.065(5) Uiso d . 1 . . H
  O6 0.81622(12) 0.4285(3) 0.50194(7) 0.0232(4) Uani d . 1 . . O
  H61 0.848(3) 0.533(6) 0.4894(15) 0.065(5) Uiso d . 1 . . H
  C1 0.68405(17) 0.6179(4) 0.56779(9) 0.0189(5) Uani d . 1 . . C
  O7 0.73139(12) 0.8296(3) 0.56021(7) 0.0216(4) Uani d . 1 . . O
  H71 0.696(3) 0.907(6) 0.5385(14) 0.065(5) Uiso d . 1 . . H
  C2 0.73415(16) 0.5004(4) 0.61681(9) 0.0180(5) Uani d . 1 . . C
  C4 0.74655(17) 0.1842(4) 0.67865(9) 0.0220(5) Uani d . 1 . . C
  H4 0.7270(19) 0.043(5) 0.6880(11) 0.029(4) Uiso d . 1 . . H
  C3 0.70156(17) 0.2900(4) 0.63368(9) 0.0193(5) Uani d . 1 . . C
  H3 0.648(2) 0.222(4) 0.6148(11) 0.029(4) Uiso d . 1 . . H
  C5 0.82277(17) 0.2920(4) 0.70627(9) 0.0219(5) Uani d . 1 . . C
  C7 0.81133(17) 0.6035(4) 0.64551(10) 0.0218(5) Uani d . 1 . . C
  H7 0.8325(19) 0.747(5) 0.6341(10) 0.029(4) Uiso d . 1 . . H
  C6 0.85602(19) 0.4998(4) 0.69080(10) 0.0246(6) Uani d . 1 . . C
  H6 0.907(2) 0.565(4) 0.7089(11) 0.029(4) Uiso d . 1 . . H
  N4 0.87190(15) 0.1800(4) 0.75356(8) 0.0289(5) Uani d . 1 . . N
  O41 0.84879(16) -0.0120(4) 0.76432(8) 0.0473(6) Uani d . 1 . . O
  O42 0.93419(14) 0.2852(3) 0.78042(8) 0.0414(5) Uani d . 1 . . O
  O11 0.92447(13) 0.7322(3) 0.46287(8) 0.0335(5) Uani d . 1 . . O
  C21 0.8821(2) 0.9534(4) 0.45821(12) 0.0295(6) Uani d . 1 . . C
  H21A 0.881(2) 1.009(6) 0.4946(14) 0.056(3) Uiso d . 1 . . H
  H21B 0.814(2) 0.938(5) 0.4458(13) 0.056(3) Uiso d . 1 . . H
  C31 0.9452(2) 1.0794(5) 0.41805(12) 0.0336(6) Uani d . 1 . . C
  H31A 0.992(2) 1.188(6) 0.4375(13) 0.056(3) Uiso d . 1 . . H
  H31B 0.905(2) 1.157(6) 0.3907(14) 0.056(3) Uiso d . 1 . . H
  C41 1.0075(3) 0.9009(5) 0.39057(15) 0.0455(8) Uani d . 1 . . C
  H41A 1.002(2) 0.910(6) 0.3516(14) 0.056(3) Uiso d . 1 . . H
  H41B 1.082(2) 0.914(6) 0.4001(13) 0.056(3) Uiso d . 1 . . H
  C51 0.9700(2) 0.6830(5) 0.41096(12) 0.0345(7) Uani d . 1 . . C
  H51A 1.018(2) 0.571(6) 0.4177(13) 0.056(3) Uiso d . 1 . . H
  H51B 0.915(2) 0.631(6) 0.3875(14) 0.056(3) Uiso d . 1 . . H
  O12 0.40979(14) 0.8747(3) 0.69089(7) 0.0362(5) Uani d . 1 . . O
  C22 0.4222(2) 1.0604(5) 0.72818(13) 0.0486(8) Uani d . 1 . . C
  H22A 0.4893 1.0978 0.7329 0.058 Uiso calc R 1 . . H
  H22B 0.3973 1.0242 0.7637 0.058 Uiso calc R 1 . . H
  C32 0.3683(2) 1.2484(5) 0.70312(14) 0.0493(8) Uani d . 1 . . C
  H32A 0.4079 1.3308 0.6784 0.059 Uiso calc R 1 . . H
  H32B 0.3460 1.3486 0.7310 0.059 Uiso calc R 1 . . H
  C42 0.2835(2) 1.1382(5) 0.67178(12) 0.0362(7) Uani d . 1 . . C
  H42A 0.260(2) 1.233(6) 0.6406(14) 0.056(3) Uiso d . 1 . . H
  H42B 0.227(2) 1.109(5) 0.6949(14) 0.056(3) Uiso d . 1 . . H
  C52 0.3276(2) 0.9221(6) 0.65306(14) 0.0460(8) Uani d . 1 . . C
  H52A 0.282(2) 0.785(6) 0.6541(13) 0.056(3) Uiso d . 1 . . H
  H52B 0.356(2) 0.937(6) 0.6173(14) 0.056(3) Uiso d . 1 . . H
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 0.0185(3) 0.0185(3) 0.0191(3) 0.0003(2) -0.0001(2) 0.0009(3)
  O1 0.0222(9) 0.0229(9) 0.0283(9) -0.0022(7) 0.0002(7) 0.0058(7)
  O3 0.0245(10) 0.0228(9) 0.0346(10) -0.0024(8) -0.0085(8) 0.0095(8)
  O2 0.0235(10) 0.0374(11) 0.0255(9) 0.0031(8) 0.0009(7) -0.0086(8)
  P2 0.0192(3) 0.0171(3) 0.0179(3) -0.0015(2) 0.0009(2) 0.0008(2)
  O4 0.0239(9) 0.0176(8) 0.0210(8) -0.0026(7) 0.0001(7) -0.0002(7)
  O5 0.0275(10) 0.0221(9) 0.0211(9) -0.0038(7) -0.0024(7) 0.0044(7)
  O6 0.0215(10) 0.0205(9) 0.0278(9) -0.0004(7) 0.0035(7) 0.0009(8)
  C1 0.0207(13) 0.0154(11) 0.0204(11) -0.0027(9) -0.0011(9) 0.0017(9)
  O7 0.0248(9) 0.0143(8) 0.0255(9) -0.0045(7) -0.0013(7) 0.0036(7)
  C2 0.0173(12) 0.0188(12) 0.0180(11) 0.0014(9) 0.0012(9) -0.0018(9)
  C4 0.0253(14) 0.0203(13) 0.0206(12) 0.0018(10) 0.0017(10) 0.0009(10)
  C3 0.0188(13) 0.0191(12) 0.0198(11) -0.0002(10) -0.0016(9) -0.0009(10)
  C5 0.0214(13) 0.0259(13) 0.0183(11) 0.0056(10) -0.0021(9) 0.0017(10)
  C7 0.0200(13) 0.0195(13) 0.0257(12) -0.0001(10) -0.0002(10) 0.0000(10)
  C6 0.0228(14) 0.0262(14) 0.0245(13) 0.0001(10) -0.0044(10) -0.0037(11)
  N4 0.0280(12) 0.0348(13) 0.0238(11) 0.0073(10) -0.0017(9) 0.0018(10)
  O41 0.0548(14) 0.0385(12) 0.0476(12) -0.0057(10) -0.0157(10) 0.0221(10)
  O42 0.0449(13) 0.0408(12) 0.0369(11) 0.0041(10) -0.0224(9) -0.0017(9)
  O11 0.0331(11) 0.0223(9) 0.0460(11) 0.0013(8) 0.0138(9) 0.0055(9)
  C21 0.0285(16) 0.0218(13) 0.0386(15) 0.0022(11) 0.0073(12) 0.0028(12)
  C31 0.0418(18) 0.0229(14) 0.0366(15) -0.0010(12) 0.0074(13) 0.0051(12)
  C41 0.056(2) 0.0323(16) 0.0501(19) 0.0049(15) 0.0281(17) 0.0074(15)
  C51 0.0374(17) 0.0265(15) 0.0401(16) 0.0046(13) 0.0095(13) -0.0020(13)
  O12 0.0362(11) 0.0425(12) 0.0299(10) 0.0092(9) 0.0022(8) -0.0086(9)
  C22 0.051(2) 0.053(2) 0.0412(17) 0.0139(16) -0.0081(15) -0.0182(16)
  C32 0.052(2) 0.0384(17) 0.057(2) 0.0014(15) -0.0035(16) -0.0036(16)
  C42 0.0321(17) 0.0438(18) 0.0330(15) 0.0031(13) 0.0044(12) 0.0024(13)
  C52 0.0305(18) 0.059(2) 0.0477(19) 0.0105(15) -0.0053(14) -0.0160(17)
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 . 1.5034(17) yes
  P1 O2 . 1.5637(18) yes
  P1 O3 . 1.5553(18) yes
  P1 C1 . 1.889(2) yes
  O2 H21 . 0.87(4) ?
  O3 H31 . 0.80(4) ?
  P2 O4 . 1.5044(16) yes
  P2 O5 . 1.5615(17) yes
  P2 O6 . 1.5881(18) yes
  P2 C1 . 1.870(2) yes
  O5 H51 . 0.94(4) ?
  O6 H61 . 0.84(4) ?
  C1 O7 . 1.452(3) ?
  C1 C2 . 1.540(3) ?
  O7 H71 . 0.86(4) ?
  C2 C7 . 1.412(3) ?
  C2 C3 . 1.414(3) ?
  C4 C3 . 1.402(3) ?
  C4 C5 . 1.403(3) ?
  C4 H4 . 0.93(3) ?
  C3 H3 . 0.96(3) ?
  C5 C6 . 1.392(4) ?
  C5 N4 . 1.487(3) ?
  C7 C6 . 1.401(3) ?
  C7 H7 . 0.96(3) ?
  C6 H6 . 0.92(3) ?
  N4 O41 . 1.232(3) ?
  N4 O42 . 1.247(3) ?
  O11 C21 . 1.461(3) ?
  O11 C51 . 1.469(3) ?
  C21 C31 . 1.542(4) ?
  C21 H21A . 0.95(3) ?
  C21 H21B . 0.99(3) ?
  C31 C41 . 1.551(4) ?
  C31 H31A . 1.03(3) ?
  C31 H31B . 0.98(3) ?
  C41 C51 . 1.505(4) ?
  C41 H41A . 0.95(3) ?
  C41 H41B . 1.06(3) ?
  C51 H51A . 0.96(3) ?
  C51 H51B . 0.99(3) ?
  O12 C22 . 1.450(3) ?
  O12 C52 . 1.480(3) ?
  C22 C32 . 1.481(4) ?
  C22 H22A . 0.9700 ?
  C22 H22B . 0.9700 ?
  C32 C42 . 1.543(4) ?
  C32 H32A . 0.9700 ?
  C32 H32B . 0.9700 ?
  C42 C52 . 1.518(4) ?
  C42 H42A . 1.00(3) ?
  C42 H42B . 1.00(3) ?
  C52 H52A . 1.04(3) ?
  C52 H52B . 0.98(3) ?