#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/03/4020389.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_4020389
loop_
_publ_author_name
'Diana S. Stoianova'
'Alan Whitehead'
'Paul R. Hanson'
_publ_section_title
;
 P-Heterocyclic Building Blocks:  Application to the
 Stereoselective Synthesis of P-Sugars.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5880
_journal_page_last               5889
_journal_paper_doi               10.1021/jo0505122
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C11 H14 N3 O5 P'
_chemical_formula_sum            'C11 H14 N3 O5 P'
_chemical_formula_weight         299.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                79.409(4)
_cell_angle_beta                 74.124(4)
_cell_angle_gamma                81.613(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1636(13)
_cell_length_b                   8.7184(14)
_cell_length_c                   10.1021(16)
_cell_measurement_temperature    100(2)
_cell_volume                     676.31(19)
_diffrn_ambient_temperature      100(2)
_exptl_crystal_density_diffrn    1.469
_cod_database_code               4020389
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6230(2) 0.69380(18) 0.41110(16) 0.0190(4) Uani 1 1 d . . .
P2 P 0.72952(7) 0.65339(7) 0.52368(6) 0.0170(2) Uani 1 1 d . . .
C3 C 0.9197(3) 0.7519(3) 0.4389(2) 0.0179(5) Uani 1 1 d . . .
H3 H 0.9881 0.6916 0.3633 0.021 Uiso 1 1 calc R . .
C4 C 0.8773(3) 0.9184(3) 0.3690(2) 0.0181(5) Uani 1 1 d . . .
H4 H 0.9865 0.9633 0.3158 0.022 Uiso 1 1 calc R . .
C5 C 0.7669(3) 0.9187(3) 0.2681(2) 0.0200(5) Uani 1 1 d . . .
H5 H 0.7459 1.0286 0.2214 0.024 Uiso 1 1 calc R . .
C6 C 0.5939(3) 0.8554(3) 0.3421(2) 0.0199(5) Uani 1 1 d . . .
H6 H 0.5299 0.9223 0.4140 0.024 Uiso 1 1 calc R . .
O7 O 0.7570(2) 0.48232(19) 0.56259(18) 0.0229(4) Uani 1 1 d . . .
O8 O 0.6352(2) 0.74187(18) 0.65168(16) 0.0188(4) Uani 1 1 d . . .
C9 C 0.4900(3) 0.6915(3) 0.7535(2) 0.0180(5) Uani 1 1 d . . .
C10 C 0.3603(3) 0.6350(3) 0.7184(3) 0.0237(5) Uani 1 1 d . . .
H10 H 0.3690 0.6242 0.6248 0.028 Uiso 1 1 calc R . .
C11 C 0.2172(3) 0.5947(3) 0.8236(3) 0.0296(6) Uani 1 1 d . . .
H11 H 0.1269 0.5552 0.8018 0.036 Uiso 1 1 calc R . .
C12 C 0.2039(3) 0.6109(3) 0.9591(3) 0.0302(6) Uani 1 1 d . . .
H12 H 0.1050 0.5826 1.0300 0.036 Uiso 1 1 calc R . .
C13 C 0.3351(4) 0.6686(3) 0.9923(3) 0.0315(6) Uani 1 1 d . . .
H13 H 0.3257 0.6808 1.0857 0.038 Uiso 1 1 calc R . .
C14 C 0.4802(3) 0.7085(3) 0.8884(3) 0.0244(6) Uani 1 1 d . . .
H14 H 0.5713 0.7469 0.9101 0.029 Uiso 1 1 calc R . .
O15 O 1.0246(2) 0.74969(19) 0.53117(17) 0.0213(4) Uani 1 1 d . . .
H15 H 1.1065 0.6793 0.5165 0.026 Uiso 1 1 calc R . .
O16 O 0.7873(2) 1.01513(19) 0.46859(16) 0.0209(4) Uani 1 1 d . . .
H16 H 0.8468 1.0867 0.4669 0.025 Uiso 1 1 calc R . .
N17 N 0.8673(3) 0.8208(2) 0.1610(2) 0.0237(5) Uani 1 1 d . . .
N18 N 0.8508(3) 0.8680(3) 0.0422(2) 0.0269(5) Uani 1 1 d . . .
N19 N 0.8462(3) 0.8976(3) -0.0711(2) 0.0422(7) Uani 1 1 d . . .
C20 C 0.4831(3) 0.8476(3) 0.2470(3) 0.0264(6) Uani 1 1 d . . .
H20A H 0.5412 0.7752 0.1812 0.040 Uiso 1 1 d R . .
H20B H 0.4623 0.9523 0.1955 0.040 Uiso 1 1 d R . .
H20C H 0.3737 0.8104 0.3023 0.040 Uiso 1 1 d R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.469(3) . ?
O1 P2 1.5742(17) . ?
P2 O7 1.4712(17) . ?
P2 O8 1.5838(16) . ?
P2 C3 1.809(2) . ?
C3 O15 1.424(3) . ?
C3 C4 1.528(3) . ?
C3 H3 1.0000 . ?
C4 O16 1.411(3) . ?
C4 C5 1.534(3) . ?
C4 H4 1.0000 . ?
C5 N17 1.491(3) . ?
C5 C6 1.535(3) . ?
C5 H5 1.0000 . ?
C6 C20 1.505(3) . ?
C6 H6 1.0000 . ?
O8 C9 1.405(3) . ?
C9 C14 1.376(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O15 H15 0.8400 . ?
O16 H16 0.8400 . ?
N17 N18 1.232(3) . ?
N18 N19 1.136(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
