#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013328.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_2013328
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o289
_journal_page_last  o292
_publ_section_title
;
Two members of the bisphosphonate class of drugs:
a zwitterion and a molecular compound
;
loop_
_publ_author_name
  'Fern\'andez, Daniel'
  'Vega, Daniel'
  'Ellena, Javier A.'
_chemical_formula_moiety  'C3 H11 N O6 P2'
_chemical_formula_sum  'C3 H11 N O6 P2'
_chemical_formula_iupac  'C3 H11 N O6 P2'
_chemical_formula_weight  219.07
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  11.666(3)
_cell_length_b  12.937(5)
_cell_length_c  5.714(3)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  862.4(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.687
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
  C1 0.3046(3) 0.1974(3) 0.2458(6) 0.0194(7) Uani d . 1 . . C
  C2 0.3630(4) 0.3046(3) 0.2556(8) 0.0294(9) Uani d . 1 . . C
  H4 0.4358 0.2965 0.3356 0.038 Uiso calc R 1 . . H
  H5 0.3799 0.3256 0.0963 0.038 Uiso calc R 1 . . H
  C3 0.2981(5) 0.3927(4) 0.3736(12) 0.0602(17) Uani d . 1 . . C
  H6 0.3455 0.4534 0.3767 0.078 Uiso calc R 1 . . H
  H7 0.2788 0.3731 0.5308 0.078 Uiso calc R 1 . . H
  H8 0.2292 0.407 0.2876 0.078 Uiso calc R 1 . . H
  N1 0.2784(3) 0.1605(3) 0.4907(5) 0.0201(7) Uani d . 1 . . N
  H1 0.2386 0.2088 0.5662 0.026 Uiso calc R 1 . . H
  H2 0.3437 0.1485 0.5666 0.026 Uiso calc R 1 . . H
  H3 0.2375 0.1025 0.4837 0.026 Uiso calc R 1 . . H
  O1 0.3562(2) -0.0034(2) 0.1576(5) 0.0266(6) Uani d . 1 . . O
  O2 0.4278(2) 0.1353(2) -0.1309(5) 0.0251(6) Uani d . 1 . . O
  O3 0.5133(2) 0.1115(2) 0.2768(5) 0.0270(6) Uani d D 1 . . O
  H9 0.563(3) 0.154(3) 0.249(9) 0.041 Uiso d D 1 . . H
  O4 0.0868(3) 0.2492(3) 0.2775(5) 0.0356(8) Uani d D 1 . . O
  H10 0.031(4) 0.284(4) 0.223(9) 0.053 Uiso d D 1 . . H
  O5 0.1255(3) 0.0911(3) 0.0553(6) 0.0342(7) Uani d D 1 . . O
  H11 0.133(5) 0.062(4) -0.075(6) 0.051 Uiso d D 1 . . H
  O6 0.1756(2) 0.2640(2) -0.1304(5) 0.0285(7) Uani d . 1 . . O
  P1 0.40511(8) 0.10223(7) 0.11730(16) 0.0190(2) Uani d . 1 . . P
  P2 0.16606(8) 0.20277(8) 0.09051(18) 0.0224(2) Uani d . 1 . . P
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
  C1 0.0202(17) 0.0254(19) 0.0125(16) -0.0028(15) 0.0000(14) -0.0003(16)
  C2 0.032(2) 0.0248(19) 0.031(2) -0.0083(17) 0.0041(18) -0.0011(19)
  C3 0.067(3) 0.031(2) 0.083(5) -0.006(2) 0.031(4) -0.015(3)
  N1 0.0203(16) 0.0268(17) 0.0134(15) 0.0002(14) 0.0002(13) -0.0007(13)
  O1 0.0281(14) 0.0252(14) 0.0265(15) -0.0021(12) -0.0025(12) 0.0005(12)
  O2 0.0222(13) 0.0367(15) 0.0165(14) -0.0040(11) -0.0007(12) 0.0020(11)
  O3 0.0192(14) 0.0362(16) 0.0256(15) -0.0051(12) -0.0039(12) 0.0035(13)
  O4 0.0328(16) 0.056(2) 0.0181(15) 0.0182(16) 0.0056(13) 0.0035(14)
  O5 0.0347(16) 0.0401(18) 0.0277(16) -0.0084(14) -0.0068(14) 0.0006(14)
  O6 0.0297(15) 0.0386(16) 0.0173(14) 0.0121(12) 0.0013(12) 0.0040(12)
  P1 0.0175(4) 0.0234(4) 0.0162(4) -0.0005(4) 0.0006(4) 0.0006(4)
  P2 0.0209(5) 0.0313(5) 0.0151(4) 0.0045(4) 0.0006(4) 0.0011(4)
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
  C2 C3 . 1.526(7) ?
  C2 H4 . 0.97 ?
  C2 H5 . 0.97 ?
  C3 H6 . 0.96 ?
  C3 H7 . 0.96 ?
  C3 H8 . 0.96 ?
  N1 H1 . 0.89 ?
  N1 H2 . 0.89 ?
  N1 H3 . 0.89 ?
  O1 P1 . 1.498(3) y
  O2 P1 . 1.505(3) y
  O3 P1 . 1.561(3) y
  C1 P1 . 1.852(4) y
  O3 H9 . 0.82(3) ?
  O4 P2 . 1.536(3) y
  O4 H10 . 0.85(3) ?
  O5 P2 . 1.533(3) y
  O5 H11 . 0.84(3) ?
  O6 P2 . 1.494(3) y
  C1 C2 . 1.546(5) ?
  C1 P2 . 1.845(4) y
  C1 N1 . 1.510(5) y
_cod_database_code 2013328