data_2008353
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  622
_journal_page_last  624
_publ_section_title
;
Spiro[1-azabicyclo[5.3.0]decane-6,2'(5'H)-furan]-5',10-dione: an
example of kryptoracemic crystallization
;
loop_
_publ_author_name
  'Lynch, Vincent M.'
  'Bur, Scott K.'
  'Martin, Stephen F.'
_chemical_formula_sum  'C12 H15 N O3'
_chemical_formula_weight  221.25
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  9.1530(10)
_cell_length_b  11.4950(10)
_cell_length_c  10.2770(10)
_cell_angle_alpha  90.00
_cell_angle_beta  93.161(4)
_cell_angle_gamma  90.00
_cell_volume  1079.6(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  183(2)
_exptl_crystal_density_diffrn  1.361
_diffrn_ambient_temperature  183(2)
_refine_ls_R_factor_obs  0.0337
_refine_ls_wR_factor_obs  0.0796
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  N1 0.20620(15) 0.64223(14) 0.42545(14) 0.0227(3) Uani d . 1 . N
  C2 0.1483(2) 0.7600(2) 0.4269(2) 0.0337(4) Uani d . 1 . C
  C3 0.1807(2) 0.8331(2) 0.3092(2) 0.0315(4) Uani d . 1 . C
  C4 0.3377(2) 0.8759(2) 0.3077(3) 0.0383(5) Uani d . 1 . C
  C5 0.4498(2) 0.7857(2) 0.2692(2) 0.0324(4) Uani d . 1 . C
  C6 0.4628(2) 0.6757(2) 0.3530(2) 0.0224(3) Uani d . 1 . C
  C7 0.3234(2) 0.6000(2) 0.3454(2) 0.0221(3) Uani d . 1 . C
  C8 0.3475(2) 0.4756(2) 0.3967(2) 0.0320(4) Uani d . 1 . C
  C9 0.1990(2) 0.4405(2) 0.4450(2) 0.0353(4) Uani d . 1 . C
  C10 0.1310(2) 0.5549(2) 0.4792(2) 0.0263(4) Uani d . 1 . C
  O10 0.02425(14) 0.5682(2) 0.54517(13) 0.0356(3) Uani d . 1 . O
  O1' 0.49661(13) 0.70781(12) 0.48776(11) 0.0239(3) Uani d . 1 . O
  O2' 0.68326(14) 0.68497(15) 0.63603(13) 0.0316(3) Uani d . 1 . O
  C2' 0.6332(2) 0.6673(2) 0.5277(2) 0.0237(3) Uani d . 1 . C
  C3' 0.6937(2) 0.6055(2) 0.4173(2) 0.0297(4) Uani d . 1 . C
  C4' 0.5954(2) 0.6071(2) 0.3177(2) 0.0294(4) Uani d . 1 . C
  H2A 0.039(3)  0.753(3)  0.425(3)  0.050(8) Uiso d . 1 . H
  H2B 0.196(3)  0.802(3)  0.496(3)  0.051(8) Uiso d . 1 . H
  H3A 0.151(3)  0.789(3)  0.230(3)  0.039(7) Uiso d . 1 . H
  H3B 0.113(3)  0.898(3)  0.313(2)  0.039(7) Uiso d . 1 . H
  H4A 0.372(3)  0.909(3)  0.392(3)  0.055(8) Uiso d . 1 . H
  H4B 0.346(3)  0.945(3)  0.254(3)  0.036(6) Uiso d . 1 . H
  H5A 0.428(3)  0.755(3)  0.173(3)  0.050(8) Uiso d . 1 . H
  H5B 0.547(3)  0.824(3)  0.270(3)  0.053(8) Uiso d . 1 . H
  H7 0.293(2)  0.596(3)  0.259(2)  0.031(6) Uiso d . 1 . H
  H8A 0.424(3)  0.482(3)  0.468(2)  0.034(6) Uiso d . 1 . H
  H8B 0.387(3)  0.428(3)  0.337(3)  0.042(7) Uiso d . 1 . H
  H9A 0.199(3)  0.391(3)  0.514(3)  0.049(8) Uiso d . 1 . H
  H9B 0.144(3)  0.411(3)  0.370(3)  0.048(8) Uiso d . 1 . H
  H3' 0.797(3)  0.574(3)  0.432(2)  0.037(7) Uiso d . 1 . H
  H4' 0.597(3)  0.578(3)  0.235(3)  0.042(7) Uiso d . 1 . H
  N1A 0.3302(2) 0.55858(15) -0.1081(2) 0.0265(3) Uani d . 1 . N
  C2A 0.4309(3) 0.6519(3) -0.1453(3) 0.0295(5) Uani d P 0.76 . C
  H2AA 0.5036(3) 0.6191(3) -0.1983(3) 0.035 Uiso d PR 0.76 . H
  H2AB 0.4803(3) 0.6821(3) -0.0677(3) 0.035 Uiso d PR 0.76 . H
  C2B 0.4075(15) 0.6268(13) -0.1974(14) 0.053(3) Uiso d P 0.24 . C
  C3A 0.3565(2) 0.7505(2) -0.2180(2) 0.0368(5) Uani d . 1 . C
  C4A 0.2391(2) 0.8074(2) -0.1404(2) 0.0371(5) Uani d . 1 . C
  C5A 0.0891(2) 0.7504(2) -0.1603(2) 0.0289(4) Uani d . 1 . C
  C6A 0.0704(2) 0.6271(2) -0.1067(2) 0.0205(3) Uani d . 1 . C
  C7A 0.1786(2) 0.5366(2) -0.1567(2) 0.0239(3) Uani d . 1 . C
  C8A 0.1527(2) 0.4116(2) -0.1075(2) 0.0304(4) Uani d . 1 . C
  C9A 0.2630(2) 0.3954(2) 0.0091(2) 0.0342(4) Uani d . 1 . C
  C10A 0.3803(2) 0.4838(2) -0.0154(2) 0.0274(4) Uani d . 1 . C
  O10A 0.50212(15) 0.4878(2) 0.0399(2) 0.0401(4) Uani d . 1 . O
  O1'A 0.08751(12) 0.62789(12) 0.03498(11) 0.0237(3) Uani d . 1 . O
  C2'A -0.0416(2) 0.5963(2) 0.0870(2) 0.0274(4) Uani d . 1 . C
  O2'A -0.0508(2) 0.5873(2) 0.20248(13) 0.0440(4) Uani d . 1 . O
  C3'A -0.1511(2) 0.5772(2) -0.0215(2) 0.0279(4) Uani d . 1 . C
  C4'A -0.0871(2) 0.5927(2) -0.1329(2) 0.0247(3) Uani d . 1 . C
  H3AA 0.312(3)  0.724(3)  -0.308(3)  0.049(8) Uiso d . 1 . H
  H3AB 0.431(3)  0.806(3)  -0.232(3)  0.054(9) Uiso d . 1 . H
  H4AA 0.270(3)  0.810(3)  -0.046(3)  0.038(7) Uiso d . 1 . H
  H4AB 0.227(3)  0.888(4)  -0.174(3)  0.066(10) Uiso d . 1 . H
  H5AA 0.069(3)  0.746(3)  -0.259(3)  0.049(8) Uiso d . 1 . H
  H5AB 0.014(3)  0.796(2)  -0.121(2)  0.030(6) Uiso d . 1 . H
  H7A 0.171(2)  0.539(3)  -0.248(2)  0.030(6) Uiso d . 1 . H
  H8AA 0.166(3)  0.356(3)  -0.170(3)  0.048(8) Uiso d . 1 . H
  H8AB 0.053(3)  0.397(3)  -0.084(3)  0.044(7) Uiso d . 1 . H
  H9AA 0.310(3)  0.320(3)  0.016(3)  0.060(9) Uiso d . 1 . H
  H9AB 0.210(3)  0.417(3)  0.101(3)  0.055(8) Uiso d . 1 . H
  H3'A -0.253(3)  0.553(2)  -0.010(2)  0.031(6) Uiso d . 1 . H
  H4'A -0.128(2)  0.591(2)  -0.218(2)  0.024(5) Uiso d . 1 . 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 0.0170(6) 0.0257(7) 0.0252(6) 0.0032(5) 0.0004(5) 0.0004(6)
  C2 0.0339(10) 0.0305(10) 0.0372(10) 0.0124(8) 0.0048(8) -0.0009(8)
  C3 0.0285(9) 0.0268(9) 0.0381(10) 0.0057(7) -0.0083(7) 0.0043(8)
  C4 0.0350(10) 0.0263(10) 0.0522(13) -0.0011(8) -0.0101(9) 0.0086(9)
  C5 0.0272(9) 0.0371(10) 0.0324(9) -0.0044(8) -0.0020(7) 0.0119(8)
  C6 0.0191(7) 0.0275(8) 0.0203(7) 0.0012(6) -0.0007(5) 0.0000(6)
  C7 0.0188(7) 0.0237(8) 0.0236(7) 0.0018(6) 0.0000(5) -0.0030(6)
  C8 0.0276(9) 0.0227(9) 0.0458(11) 0.0037(7) 0.0030(8) 0.0020(8)
  C9 0.0328(10) 0.0277(10) 0.0455(12) -0.0038(8) 0.0043(8) 0.0042(9)
  C10 0.0187(7) 0.0337(10) 0.0259(8) 0.0003(7) -0.0037(6) 0.0027(7)
  O10 0.0219(6) 0.0538(10) 0.0315(6) -0.0005(6) 0.0039(5) 0.0057(7)
  O1' 0.0182(5) 0.0301(7) 0.0231(5) 0.0028(5) -0.0016(4) -0.0012(5)
  O2' 0.0257(6) 0.0409(8) 0.0275(6) -0.0020(6) -0.0052(5) 0.0041(6)
  C2' 0.0171(7) 0.0272(8) 0.0269(8) -0.0010(6) 0.0002(6) 0.0050(7)
  C3' 0.0177(7) 0.0385(10) 0.0334(8) 0.0035(7) 0.0050(6) 0.0012(8)
  C4' 0.0210(7) 0.0406(11) 0.0271(8) 0.0035(8) 0.0069(6) -0.0020(8)
  N1A 0.0197(6) 0.0275(8) 0.0330(7) 0.0024(6) 0.0059(5) 0.0056(6)
  C2A 0.0169(9) 0.0343(14) 0.0378(14) -0.0053(9) 0.0071(9) 0.0083(12)
  C3A 0.0361(10) 0.0319(10) 0.0441(11) -0.0025(9) 0.0187(9) 0.0073(9)
  C4A 0.0360(10) 0.0284(10) 0.0482(12) -0.0085(8) 0.0132(9) -0.0075(9)
  C5A 0.0286(8) 0.0239(8) 0.0348(9) -0.0003(7) 0.0063(7) 0.0011(7)
  C6A 0.0186(6) 0.0230(8) 0.0198(7) 0.0004(6) -0.0012(5) -0.0021(6)
  C7A 0.0250(8) 0.0268(9) 0.0196(7) 0.0048(7) -0.0023(6) -0.0024(7)
  C8A 0.0241(8) 0.0231(9) 0.0427(11) 0.0001(7) -0.0083(7) -0.0052(8)
  C9A 0.0253(8) 0.0299(10) 0.0466(12) -0.0035(8) -0.0061(8) 0.0123(9)
  C10A 0.0207(7) 0.0296(9) 0.0319(9) 0.0004(7) 0.0023(6) 0.0011(7)
  O10A 0.0215(6) 0.0477(9) 0.0501(9) -0.0017(6) -0.0076(6) 0.0033(8)
  O1'A 0.0191(5) 0.0329(7) 0.0190(5) -0.0037(5) 0.0003(4) -0.0047(5)
  C2'A 0.0215(7) 0.0318(9) 0.0291(8) -0.0035(7) 0.0045(6) -0.0037(8)
  O2'A 0.0393(7) 0.0676(12) 0.0259(6) -0.0102(8) 0.0093(5) -0.0047(7)
  C3'A 0.0182(7) 0.0292(9) 0.0362(9) -0.0027(6) 0.0002(6) -0.0017(8)
  C4'A 0.0202(7) 0.0248(8) 0.0285(8) -0.0003(6) -0.0059(6) -0.0027(7)
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 C10 . 1.352(2) ?
  N1 C2 . 1.454(3) ?
  N1 C7 . 1.470(2) ?
  C2 C3 . 1.515(3) ?
  C2 H2A . 1.01(3) ?
  C2 H2B . 0.94(3) ?
  C3 C4 . 1.520(3) ?
  C3 H3A . 0.98(3) ?
  C3 H3B . 0.97(3) ?
  C4 C5 . 1.526(3) ?
  C4 H4A . 0.98(3) ?
  C4 H4B . 0.97(3) ?
  C5 C6 . 1.530(3) ?
  C5 H5A . 1.06(3) ?
  C5 H5B . 0.99(3) ?
  C6 O1' . 1.450(2) ?
  C6 C4' . 1.509(2) ?
  C6 C7 . 1.543(2) ?
  C7 C8 . 1.536(3) ?
  C7 H7 . 0.91(2) ?
  C8 C9 . 1.527(3) ?
  C8 H8A . 0.98(2) ?
  C8 H8B . 0.91(3) ?
  C9 C10 . 1.505(3) ?
  C9 H9A . 0.91(3) ?
  C9 H9B . 0.96(3) ?
  C10 O10 . 1.229(2) ?
  O1' C2' . 1.375(2) ?
  O2' C2' . 1.198(2) ?
  C2' C3' . 1.472(3) ?
  C3' C4' . 1.326(3) ?
  C3' H3' . 1.02(2) ?
  C4' H4' . 0.91(3) ?
  N1A C10A . 1.345(2) ?
  N1A C2B . 1.424(14) ?
  N1A C7A . 1.470(2) ?
  N1A C2A . 1.478(3) ?
  C2A C2B . 0.634(13) ?
  C2A C3A . 1.500(4) ?
  C2A H2AA . 0.96 ?
  C2A H2AB . 0.96 ?
  C2B C3A . 1.51(2) ?
  C3A C4A . 1.521(3) ?
  C3A H3AA . 1.04(3) ?
  C3A H3AB . 0.95(3) ?
  C4A C5A . 1.524(3) ?
  C4A H4AA . 1.00(3) ?
  C4A H4AB . 1.00(4) ?
  C5A C6A . 1.534(3) ?
  C5A H5AA . 1.02(3) ?
  C5A H5AB . 0.97(3) ?
  C6A O1'A . 1.456(2) ?
  C6A C4'A . 1.504(2) ?
  C6A C7A . 1.543(2) ?
  C7A C8A . 1.546(3) ?
  C7A H7A . 0.93(2) ?
  C8A C9A . 1.535(3) ?
  C8A H8AA . 0.91(3) ?
  C8A H8AB . 0.98(3) ?
  C9A C10A . 1.509(3) ?
  C9A H9AA . 0.97(4) ?
  C9A H9AB . 1.11(3) ?
  C10A O10A . 1.224(2) ?
  O1'A C2'A . 1.373(2) ?
  C2'A O2'A . 1.199(2) ?
  C2'A C3'A . 1.474(2) ?
  C3'A C4'A . 1.327(3) ?
  C3'A H3'A . 0.99(2) ?
  C4'A H4'A . 0.93(2) ?