#------------------------------------------------------------------------------
#$Date: 2009-11-18 14:56:34 +0000 (Wed, 18 Nov 2009) $
#$Revision: 858 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010185.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_2010185
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1994
_journal_volume 50
_journal_page_first  1734
_journal_page_last  1738
_publ_section_title
;
Two Nitrogen-Containing Analogues of Chorismic Acid
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Mackay, M.F.'
  'McLeish, M.J.'
  'Campbell, M.'
_chemical_formula_moiety  'C13 H23 N1 O5'
_chemical_formula_sum            'C13 H23 N O5'
_[local]_cod_chemical_formula_sum_orig 'C13 H23 N1 O5'
_chemical_formula_weight  273.3
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,-y,-z'
  '1/2-x,1/2+y,1/2-z'
  '1/2+x,1/2-y,1/2+z'
_cell_length_a  14.2140(10)
_cell_length_b  6.5930(10)
_cell_length_c  16.5430(10)
_cell_angle_alpha  90.0
_cell_angle_beta  99.510(10)
_cell_angle_gamma  90.0
_cell_volume  1529.0(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  291.0(10)
_exptl_crystal_density_diffrn  1.187
_exptl_crystal_density_meas  1.189(5)
_diffrn_ambient_temperature  291.0(10)
_refine_ls_R_factor_obs  0.070
_refine_ls_wR_factor_obs  0.075
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
  C1 0.3059(4) -0.0170(8) 0.5034(3)
  C2 0.3630(4) 0.0489(9) 0.4356(3)
  C3 0.3186(3) -0.0193(6) 0.3494(2)
  C4 0.2151(3) 0.0474(6) 0.3305(2)
  C5 0.1604(3) -0.0413(8) 0.3931(3)
  C6 0.2005(5) 0.0308(10) 0.4784(3)
  C1' 0.3228(5) -0.2366(8) 0.5275(4)
  O1' 0.2652(3) -0.3616(7) 0.5267(4)
  O2' 0.4104(3) -0.2748(6) 0.5565(3)
  C2' 0.4352(4) -0.4687(8) 0.5953(4)
  O4 0.1748(2) -0.0127(5) 0.2491(2)
  N3 0.3733(2) 0.0620(5) 0.2903(2)
  C7' 0.4465(2) -0.0354(6) 0.2673(2)
  O7' 0.4679(2) -0.2113(4) 0.2827(2)
  O8' 0.4937(2) 0.0905(4) 0.2232(2)
  C9' 0.5734(3) 0.0200(6) 0.1842(3)
  C10' 0.6544(3) -0.0529(9) 0.2491(3)
  C11' 0.5398(4) -0.1411(9) 0.1222(3)
  C12' 0.6011(3) 0.2108(7) 0.1419(3)
  H2'a 0.5113 -0.4752 0.6160
  H2'b 0.3986 -0.4865 0.6471
  H2'c 0.4143 -0.5891 0.5518
  H10'a 0.7127 -0.1046 0.2200
  H10'b 0.6784 -0.0702 0.2904
  H10'c 0.6297 -0.1764 0.2830
  H11'a 0.5989 -0.1918 0.0938
  H11'b 0.5116 -0.2676 0.1521
  H11'c 0.4846 -0.0799 0.0758
  H12'a 0.6601 0.1775 0.1105
  H12'b 0.5401 0.2627 0.0982
  H12'c 0.6219 0.3276 0.1872
  H1 0.328(3) 0.079(7) 0.553(3)
  H2a 0.427(3) 0.015(7) 0.444(3)
  H2b 0.366(3) 0.202(7) 0.433(3)
  H3 0.320(2) -0.156(5) 0.346(2)
  H4 0.213(2) 0.200(5) 0.334(2)
  H5a 0.163(2) -0.190(6) 0.393(2)
  H5b 0.091(3) -0.003(6) 0.374(2)
  H6a 0.165(3) -0.033(7) 0.513(3)
  H6b 0.197(3) 0.198(8) 0.479(3)
  HO4 0.133(3) 0.060(6) 0.231(3)
  HN3 0.364(2) 0.188(5) 0.278(2)
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 0.119(4) 0.076(4) 0.061(3) -0.006(3) 0.028(3) 0.002(3)
  C2 0.087(4) 0.074(4) 0.066(3) -0.009(3) 0.013(3) 0.010(3)
  C3 0.055(2) 0.044(3) 0.066(3) 0.000(2) 0.028(2) 0.008(2)
  C4 0.056(2) 0.044(2) 0.062(3) 0.002(2) 0.023(2) -0.002(2)
  C5 0.061(3) 0.070(3) 0.087(4) 0.003(2) 0.041(3) 0.003(3)
  C6 0.126(5) 0.097(5) 0.083(4) 0.011(4) 0.066(4) 0.008(3)
  C1' 0.102(4) 0.075(4) 0.108(4) -0.023(4) 0.040(4) 0.010(3)
  O1' 0.128(4) 0.113(4) 0.275(6) -0.015(3) 0.020(4) 0.075(4)
  O2' 0.119(3) 0.107(3) 0.166(4) -0.016(3) -0.024(3) 0.038(3)
  C2' 0.153(6) 0.078(4) 0.163(6) 0.003(4) -0.011(5) 0.037(4)
  O4 0.062(2) 0.054(2) 0.070(2) -0.002(2) 0.011(2) -0.004(2)
  N3 0.057(2) 0.043(2) 0.079(2) 0.007(2) 0.035(2) 0.018(2)
  C7' 0.048(2) 0.052(2) 0.068(3) 0.004(2) 0.021(2) 0.009(2)
  O7' 0.063(2) 0.050(2) 0.095(2) 0.0060(10)
  0.034(2) 0.016(2)
  O8' 0.060(2) 0.057(2) 0.090(2) 0.0050(10)
  0.041(2) 0.018(2)
  C9' 0.053(2) 0.072(3) 0.087(3) 0.001(2) 0.037(2) 0.007(3)
  C10 0.053(3) 0.152(5) 0.120(4) 0.021(3) 0.025(3) 0.038(4)
  C11' 0.136(5) 0.124(5) 0.116(5) -0.030(4) 0.074(4) -0.033(4)
  C12 0.076(3) 0.100(4) 0.114(4) 0.000(3) 0.052(3) 0.036(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  C1 C2 1.551(8) yes
  C1 C6 1.520(9) yes
  C1 C1' 1.510(7) yes
  C2 C3 1.529(6) yes
  C3 C4 1.518(6) yes
  C3 N3 1.449(5) yes
  C4 C5 1.512(6) yes
  C4 O4 1.430(5) yes
  C5 C6 1.509(7) yes
  C1' O1' 1.160(8) yes
  C1' O2' 1.283(8) yes
  O2' C2' 1.448(7) yes
  N3 C7' 1.331(5) yes
  C7' O7' 1.215(5) yes
  C7' O8' 1.354(5) yes
  O8' C9' 1.469(6) yes
  C9' C10' 1.517(6) yes
  C9' C11' 1.499(7) yes
  C9' C12' 1.523(6) yes