#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008364.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_2008364
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  588
_journal_page_last  590
_publ_section_title
;
5-Methyl-2-oxido-2-oxo-6-phenyl-1,4,2-oxazoniaphosphorinan
-4-ylmethylphosphonic acid
;
loop_
_publ_author_name
  'Saint-Clair, Jean-Fran\,cois'
  'Sim\'eon, Fabrice'
  'Villemin, Didier'
  "Averbuch-Pouchot, Marie-Th\'er\`ese"
_chemical_formula_moiety  'C11 H17 N O6 P2'
_chemical_formula_sum  'C11 H17 N O6 P2'
_chemical_formula_weight  321.21
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P c a 21'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '  -x,  -y,1/2+z'
  '1/2-x,  +y,1/2+z'
  '1/2+x,  -y,  +z'
_cell_length_a  14.361(2)
_cell_length_b  13.711(2)
_cell_length_c  7.475(2)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1471.9(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.449
_diffrn_ambient_temperature  293
_refine_ls_R_factor_obs  0.0264
_refine_ls_wR_factor_obs  0.0331
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  P1 0.11052(3) 0.29634(3) 0.000 0.02590(9) Uani d ? . 1.000
  P2 0.16256(3) 0.54672(3) 0.45758(8) 0.02904(9) Uani d ? . 1.000
  O1 0.08333(9) 0.19782(9) 0.0987(2) 0.0303(3) Uani d ? . 1.000
  O2 0.21010(8) 0.29579(9) -0.0497(2) 0.0392(3) Uani d ? . 1.000
  O3 0.04143(9) 0.31280(10)
  -0.1470(2) 0.0373(3) Uani d ? . 1.000
  O4 0.15202(9) 0.59839(9) 0.6392(2) 0.0369(3) Uani d ? . 1.000
  O5 0.25900(10)
  0.52536(8) 0.3966(2) 0.0377(3) Uani d ? . 1.000
  O6 0.10830(10)
  0.60630(10)
  0.3191(2) 0.0425(4) Uani d ? . 1.000
  N 0.12371(9) 0.35640(10)
  0.3533(2) 0.0241(3) Uani d ? . 1.000
  C1 0.10330(10)
  0.43120(10)
  0.4923(3) 0.0303(4) Uani d ? . 1.000
  C2 0.09050(10)
  0.38730(10)
  0.1715(2) 0.0271(4) Uani d ? . 1.000
  C3 0.08930(10)
  0.25430(10)
  0.4049(3) 0.0287(4) Uani d ? . 1.000
  C4 0.13080(10)
  0.18400(10)
  0.2682(3) 0.0287(4) Uani d ? . 1.000
  C5 0.12620(10)
  0.07850(10)
  0.3256(3) 0.0349(5) Uani d ? . 1.000
  C6 0.1926(2) 0.04540(10)
  0.4426(4) 0.0545(6) Uani d ? . 1.000
  C7 0.1936(2) -0.0511(2) 0.4977(5) 0.0668(8) Uani d ? . 1.000
  C8 0.1275(2) -0.1144(2) 0.4351(4) 0.0619(7) Uani d ? . 1.000
  C9 0.0600(2) -0.08170(10)
  0.3172(4) 0.0571(7) Uani d ? . 1.000
  C10 0.0590(2) 0.01470(10)
  0.2629(3) 0.0450(5) Uani d ? . 1.000
  C11 -0.01590(10)
  0.24900(10)
  0.4201(3) 0.0380(5) Uani d ? . 1.000
  H1 0.2458 0.0938 0.4901 0.055 Uiso c ? . 1.000
  H2 0.2464 -0.0817 0.5766 0.063 Uiso c ? . 1.000
  H3 0.1335 -0.1808 0.4613 0.058 Uiso c ? . 1.000
  H4 0.0155 -0.1312 0.2586 0.062 Uiso c ? . 1.000
  H5 0.0121 0.0435 0.1887 0.062 Uiso c ? . 1.000
  H6 0.1974 0.2004 0.2504 0.044 Uiso c ? . 1.000
  H7 -0.0357 0.2915 0.4994 0.053 Uiso c ? . 1.000
  H8 -0.0468 0.2647 0.3107 0.049 Uiso c ? . 1.000
  H9 -0.0300 0.1834 0.4511 0.050 Uiso c ? . 1.000
  H10 0.1164 0.2405 0.5119 0.044 Uiso c ? . 1.000
  H11 0.0353 0.6419 0.3506 0.067 Uiso c ? . 1.000
  H12 0.1262 0.4053 0.6044 0.049 Uiso c ? . 1.000
  H13 0.0364 0.4383 0.5007 0.044 Uiso c ? . 1.000
  H14 0.0266 0.4001 0.1899 0.045 Uiso c ? . 1.000
  H15 0.1173 0.4513 0.1491 0.046 Uiso c ? . 1.000
  H16 0.1963 0.5749 0.7253 0.064 Uiso c ? . 1.000
  H17 0.1878 0.3478 0.3546 0.045 Uiso c ? . 1.000
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 0.0262(2) 0.0305(2) 0.0211(2) -0.0011(2) 0.0031(2) -0.0001(2)
  P2 0.0346(2) 0.0298(2) 0.0227(2) 0.0045(2) 0.0015(2) -0.0017(2)
  O1 0.0335(6) 0.0328(6) 0.0247(6) -0.0080(5) -0.0031(5) 0.0013(5)
  O2 0.0300(6) 0.0374(6) 0.0501(8) -0.0019(5) 0.0121(7) 0.0014(7)
  O3 0.0403(7) 0.0509(7) 0.0205(6) 0.0055(6) -0.0041(6) -0.0017(6)
  O4 0.0440(7) 0.0391(7) 0.0275(7) 0.0078(6) -0.0024(6) -0.0087(6)
  O5 0.0365(6) 0.0397(6) 0.0369(7) 0.0017(6) 0.0068(6) 0.0012(6)
  O6 0.0552(9) 0.0452(7) 0.0272(7) 0.0159(6) -0.0003(7) 0.0041(6)
  N 0.0250(6) 0.0279(6) 0.0194(6) 0.0003(5) -0.0004(6) 0.0012(6)
  C1 0.0346(8) 0.0350(7) 0.0213(7) 0.0026(7) 0.0033(7) -0.0012(7)
  C2 0.0300(8) 0.0314(7) 0.0199(7) 0.0034(7) -0.0018(7) 0.0000(7)
  C3 0.0320(8) 0.0293(7) 0.0246(8) -0.0043(7) -0.0026(7) 0.0053(7)
  C4 0.0303(8) 0.0292(8) 0.0266(8) -0.0037(7) -0.0024(7) 0.0010(7)
  C5 0.0430(10)
  0.0300(8) 0.0312(9) -0.0048(7) 0.0017(9) 0.0002(8)
  C6 0.0640(10)
  0.0376(9) 0.0620(10)
  -0.0020(10)
  -0.0210(10)
  0.0080(10)
  C7 0.081(2) 0.0410(10)
  0.078(2) 0.0070(10)
  -0.013(2) 0.0170(10)
  C8 0.094(2) 0.0316(9) 0.060(2) -0.0020(10)
  0.014(2) 0.0080(10)
  C9 0.091(2) 0.0370(10)
  0.0430(10)
  -0.0230(10)
  0.0100(10)
  -0.0020(10)
  C10 0.0600(10)
  0.0390(10)
  0.0360(10)
  -0.0158(9) -0.0030(10)
  0.0029(9)
  C11 0.0318(9) 0.0490(10)
  0.0340(10)
  -0.0071(8) 0.0063(8) 0.0024(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  P1 O1 . . 1.5880(10)
  yes
  P1 O2 . . 1.4780(10)
  yes
  P1 O3 . . 1.4980(10)
  yes
  P1 C2 . . 1.812(2) yes
  P2 O4 . . 1.539(2) yes
  P2 O5 . . 1.488(2) yes
  P2 O6 . . 1.532(2) yes
  P2 C1 . . 1.816(2) yes
  O1 C4 . . 1.451(2) yes
  N C2 . . 1.502(2) yes
  N C1 . . 1.489(2) no
  N C3 . . 1.534(2) no
  C3 C4 . . 1.526(3) no
  C3 C11 . . 1.517(3) no
  C4 C5 . . 1.510(3) no
  C5 C6 . . 1.372(3) no
  C5 C10 . . 1.384(3) no
  C6 C7 . . 1.386(3) no
  C7 C8 . . 1.369(4) no
  C8 C9 . . 1.385(4) no
  C9 C10 . . 1.383(3) no
  O4 H16 . . 0.96 no
  O6 H11 . . 1.18 no
  N H17 . . 0.93 no
  C1 H12 . . 0.97 no
  C1 H13 . . 0.97 no
  C2 H14 . . 0.94 no
  C2 H15 . . 0.97 no
  C3 H10 . . 0.91 no
  C4 H6 . . 0.99 no
  C6 H1 . . 1.07 no
  C7 H2 . . 1.05 no
  C8 H3 . . 0.94 no
  C9 H4 . . 1.03 no
  C10 H5 . . 0.96 no
  C11 H7 . . 0.88 no
  C11 H8 . . 0.95 no
  C11 H9 . . 0.95 no