#------------------------------------------------------------------------------
#$Date: 2010-01-30 14:59:17 +0100 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012769.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_2012769
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o367
_journal_page_last  o369
_publ_section_title
;
Precursor of a \b-lactamase inhibitor: allyl
(4S,8S,9R)-10-[(E)-ethylidene]-4-methoxy-11-oxo-1-
azatricyclo[7.2.0.0^3,8^]undec-2-ene-2-carboxylate
;
loop_
_publ_author_name
  'Leban, Ivan'
  'Seli\<c, Lovro'
  'Mesar, Toma\<z'
  '\<Copar, Anton'
  '\<Solmajer, Tom'
_chemical_name_common
;
a precursor of a \b-lactamase inhibitor
;
_chemical_formula_moiety  'C17 H21 N O4'
_chemical_formula_sum  'C17 H21 N O4'
_chemical_formula_iupac  'C17 H21 N O4'
_chemical_formula_weight  303.35
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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  7.6810(2)
_cell_length_b  14.4610(3)
_cell_length_c  14.6190(4)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1623.80(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.241
_exptl_crystal_density_meas  1.22(5)
_diffrn_ambient_temperature  293(2)
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
  N1 0.7798(3) 0.59637(13) 0.22288(15) 0.0599(5) Uani d . 1 . . N
  C2 0.8588(3) 0.54660(15) 0.14886(16) 0.0555(5) Uani d . 1 . . C
  C3 0.7880(3) 0.46227(15) 0.14023(15) 0.0536(5) Uani d . 1 . . C
  C4 0.8201(4) 0.38783(16) 0.07029(17) 0.0665(7) Uani d . 1 . . C
  H4 0.9149 0.4058 0.0291 0.080 Uiso calc R 1 . . H
  C5 0.6529(5) 0.3737(2) 0.01714(19) 0.0826(9) Uani d . 1 . . C
  H5A 0.6319 0.4276 -0.0207 0.099 Uiso calc R 1 . . H
  H5B 0.6668 0.3209 -0.0231 0.099 Uiso calc R 1 . . H
  C6 0.4961(4) 0.3578(2) 0.0780(2) 0.0787(8) Uani d . 1 . . C
  H6A 0.5105 0.2999 0.1106 0.094 Uiso calc R 1 . . H
  H6B 0.3927 0.3526 0.0402 0.094 Uiso calc R 1 . . H
  C7 0.4704(4) 0.4361(2) 0.1473(2) 0.0714(7) Uani d . 1 . . C
  H7A 0.3730 0.4218 0.1871 0.086 Uiso calc R 1 . . H
  H7B 0.4447 0.4933 0.1154 0.086 Uiso calc R 1 . . H
  C8 0.6380(3) 0.44776(15) 0.20496(15) 0.0541(5) Uani d . 1 . . C
  H8 0.6580 0.3915 0.2408 0.065 Uiso calc R 1 . . H
  C9 0.6501(3) 0.53274(16) 0.26825(16) 0.0584(5) Uani d . 1 . . C
  H9 0.6827 0.5166 0.3311 0.070 Uiso calc R 1 . . H
  C10 0.5210(3) 0.61155(18) 0.26361(19) 0.0667(7) Uani d . 1 . . C
  C11 0.6504(3) 0.66668(17) 0.21131(19) 0.0653(6) Uani d . 1 . . C
  O11 0.6559(3) 0.73935(13) 0.17230(18) 0.0898(7) Uani d . 1 . . O
  C12 1.0027(4) 0.58562(19) 0.0944(2) 0.0687(7) Uani d . 1 . . C
  O13 1.0730(4) 0.5457(2) 0.0330(2) 0.1314(12) Uani d . 1 . . O
  O14 1.0455(3) 0.66989(13) 0.11910(16) 0.0817(6) Uani d . 1 . . O
  C15 1.1857(5) 0.7139(2) 0.0673(3) 0.0962(10) Uani d . 1 . . C
  H15A 1.1839 0.6923 0.0045 0.115 Uiso calc R 1 . . H
  H15B 1.2974 0.6977 0.0939 0.115 Uiso calc R 1 . . H
  C16 1.1621(6) 0.8144(3) 0.0696(3) 0.1015(11) Uani d . 1 . . C
  H16 1.2570 0.8493 0.0504 0.122 Uiso calc R 1 . . H
  C17 1.0279(8) 0.8603(3) 0.0947(3) 0.1199(15) Uani d . 1 . . C
  H17A 0.9288 0.8294 0.1146 0.144 Uiso calc R 1 . . H
  H17B 1.0296 0.9246 0.0929 0.144 Uiso calc R 1 . . H
  O18 0.8599(3) 0.30247(12) 0.11466(13) 0.0707(5) Uani d . 1 . . O
  C19 1.0209(4) 0.3038(2) 0.1623(3) 0.0857(9) Uani d . 1 . . C
  H19A 1.0399 0.2448 0.1908 0.128 Uiso calc R 1 . . H
  H19B 1.0180 0.3512 0.2083 0.128 Uiso calc R 1 . . H
  H19C 1.1137 0.3163 0.1201 0.128 Uiso calc R 1 . . H
  C20 0.3580(4) 0.6278(2) 0.2902(2) 0.0788(8) Uani d . 1 . . C
  H20 0.3109 0.6854 0.2765 0.095 Uiso calc R 1 . . H
  C21 0.2458(4) 0.5611(3) 0.3398(3) 0.1043(12) Uani d . 1 . . C
  H21A 0.1343 0.5888 0.3513 0.156 Uiso calc PR 0.50 . . H
  H21B 0.2996 0.5449 0.3969 0.156 Uiso calc PR 0.50 . . H
  H21C 0.2308 0.5065 0.3034 0.156 Uiso calc PR 0.50 . . H
  H21D 0.3089 0.5047 0.3497 0.156 Uiso calc PR 0.50 . . H
  H21E 0.1435 0.5485 0.3042 0.156 Uiso calc PR 0.50 . . H
  H21F 0.2124 0.5870 0.3977 0.156 Uiso calc PR 0.50 . . 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
  N1 0.0539(10) 0.0542(10) 0.0717(11) -0.0043(9) 0.0027(10) -0.0126(9)
  C2 0.0494(10) 0.0536(11) 0.0634(12) 0.0016(10) 0.0010(10) -0.0015(10)
  C3 0.0588(11) 0.0492(11) 0.0527(11) 0.0007(10) 0.0006(10) 0.0001(9)
  C4 0.0860(18) 0.0527(12) 0.0606(13) 0.0044(12) 0.0084(13) -0.0039(10)
  C5 0.109(2) 0.0756(16) 0.0631(14) -0.0021(18) -0.0144(18) -0.0092(13)
  C6 0.0866(19) 0.0710(16) 0.0784(16) -0.0115(15) -0.0238(16) -0.0112(14)
  C7 0.0650(14) 0.0704(15) 0.0788(16) -0.0065(13) -0.0131(14) -0.0052(13)
  C8 0.0573(12) 0.0493(10) 0.0558(11) -0.0024(10) -0.0031(10) 0.0011(9)
  C9 0.0562(12) 0.0644(12) 0.0547(11) -0.0052(11) 0.0028(11) -0.0063(10)
  C10 0.0602(14) 0.0649(14) 0.0750(15) -0.0009(11) 0.0070(13) -0.0187(12)
  C11 0.0587(13) 0.0529(12) 0.0844(16) -0.0024(11) 0.0060(14) -0.0143(12)
  O11 0.0805(13) 0.0554(10) 0.1336(18) 0.0027(10) 0.0111(14) 0.0031(11)
  C12 0.0596(14) 0.0622(14) 0.0844(17) 0.0006(11) 0.0134(13) 0.0021(13)
  O13 0.145(2) 0.0969(16) 0.153(2) -0.0283(17) 0.090(2) -0.0286(17)
  O14 0.0744(11) 0.0680(11) 0.1028(14) -0.0179(10) 0.0240(12) -0.0043(10)
  C15 0.081(2) 0.090(2) 0.117(3) -0.0207(17) 0.0247(19) 0.0135(19)
  C16 0.109(3) 0.090(2) 0.105(2) -0.034(2) 0.024(2) 0.0053(19)
  C17 0.143(4) 0.079(2) 0.138(3) -0.016(3) 0.024(4) 0.007(2)
  O18 0.0761(11) 0.0506(8) 0.0853(12) 0.0058(9) 0.0023(10) -0.0022(8)
  C19 0.0726(17) 0.0750(17) 0.109(2) 0.0168(15) 0.0017(18) -0.0040(17)
  C20 0.0634(14) 0.0835(17) 0.0897(19) 0.0020(14) 0.0161(15) -0.0199(15)
  C21 0.076(2) 0.139(3) 0.097(2) -0.009(2) 0.0303(19) -0.014(2)
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
  N1 C11 . 1.432(3) yes
  N1 C2 . 1.434(3) yes
  N1 C9 . 1.509(3) yes
  C2 C3 . 1.341(3) yes
  C2 C12 . 1.474(3) ?
  C3 C4 . 1.505(3) ?
  C3 C8 . 1.506(3) yes
  C4 O18 . 1.428(3) ?
  C4 C5 . 1.515(4) ?
  C4 H4 . 0.9800 ?
  C5 C6 . 1.515(5) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 C7 . 1.532(4) ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 C8 . 1.548(3) ?
  C7 H7A . 0.9700 ?
  C7 H7B . 0.9700 ?
  C8 C9 . 1.541(3) yes
  C8 H8 . 0.9800 ?
  C9 C10 . 1.512(4) yes
  C9 H9 . 0.9800 ?
  C10 C20 . 1.332(4) ?
  C10 C11 . 1.486(4) yes
  C11 O11 . 1.196(3) yes
  C12 O13 . 1.197(4) ?
  C12 O14 . 1.313(3) ?
  O14 C15 . 1.462(4) ?
  C15 C16 . 1.465(5) ?
  C15 H15A . 0.9700 ?
  C15 H15B . 0.9700 ?
  C16 C17 . 1.279(6) ?
  C16 H16 . 0.9300 ?
  C17 H17A . 0.9300 ?
  C17 H17B . 0.9300 ?
  O18 C19 . 1.420(4) ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?
  C20 C21 . 1.483(5) ?
  C20 H20 . 0.9300 ?
  C21 H21A . 0.9600 ?
  C21 H21B . 0.9600 ?
  C21 H21C . 0.9600 ?
  C21 H21D . 0.9600 ?
  C21 H21E . 0.9600 ?
  C21 H21F . 0.9600 ?
_cod_database_code 2012769