#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008384.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_2008384
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  612
_journal_page_last  613
_publ_section_title
;
(R)-N-(1-hydroxybut-2-yl)pyrrolidine-2,5-dione
;
loop_
_publ_author_name
  'Pilati, Tullio'
  'G. Biju Kumar'
  'Amrish C. Shah'
_chemical_formula_sum  'C8 H13 N O3'
_chemical_formula_weight  171.2
_chemical_melting_point  323
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  9.6190(10)
_cell_length_b  10.325(2)
_cell_length_c  18.910(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1878.1(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.211
_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
  C1A 0.0576(5) 0.0453(5) 0.1379(2) 0.0834(12) Uani d . 1 . . C
  H1A1 0.092(3) 0.037(3) 0.1868(16) 0.067(9) Uiso d . 1 . . H
  H1A2 -0.027(4) 0.091(4) 0.142(2) 0.106(15) Uiso d . 1 . . H
  C2A 0.0308(4) -0.0926(3) 0.11343(16) 0.0640(9) Uani d . 1 . . C
  H2A 0.118(3) -0.146(3) 0.1179(15) 0.067(9) Uiso d . 1 . . H
  C3A -0.0736(4) -0.1633(5) 0.16051(18) 0.0897(12) Uani d . 1 . . C
  H3A1 -0.0470 -0.1515 0.2096 0.111(14) Uiso calc R 1 . . H
  H3A2 -0.1646 -0.1247 0.1541 0.138(19) Uiso calc R 1 . . H
  C4A -0.0831(6) -0.3055(5) 0.1452(2) 0.1063(15) Uani d . 1 . . C
  H4A1 -0.1500 -0.3445 0.1763 0.18(2) Uiso calc R 1 . . H
  H4A2 0.0061 -0.3450 0.1526 0.109(16) Uiso calc R 1 . . H
  H4A3 -0.1113 -0.3181 0.0970 0.132(17) Uiso calc R 1 . . H
  O5A 0.1596(3) 0.1090(3) 0.09665(15) 0.0813(7) Uani d . 1 . . O
  H5A 0.125(5) 0.131(4) 0.051(2) 0.127(16) Uiso d . 1 . . H
  N6A -0.0128(3) -0.0945(2) 0.03905(11) 0.0540(6) Uani d . 1 . . N
  C7A -0.1309(4) -0.0364(3) 0.01203(18) 0.0633(9) Uani d . 1 . . C
  C8A -0.1407(4) -0.0648(3) -0.06492(17) 0.0721(10) Uani d . 1 . . C
  H8A1 -0.1491 0.0146 -0.0920 0.073(10) Uiso calc R 1 . . H
  H8A2 -0.2202 -0.1196 -0.0749 0.104(13) Uiso calc R 1 . . H
  C9A -0.0061(4) -0.1343(3) -0.08243(17) 0.0761(10) Uani d . 1 . . C
  H9A1 -0.0247 -0.2171 -0.1047 0.107(13) Uiso calc R 1 . . H
  H9A2 0.0507 -0.0825 -0.1140 0.086(11) Uiso calc R 1 . . H
  C10A 0.0646(4) -0.1525(3) -0.01331(16) 0.0586(8) Uani d . 1 . . C
  O11A -0.2113(3) 0.0266(3) 0.04706(14) 0.0884(8) Uani d . 1 . . O
  O12A 0.1740(3) -0.2076(2) -0.00245(12) 0.0807(7) Uani d . 1 . . O
  C1B -0.1169(5) 0.2490(5) -0.2179(2) 0.0803(12) Uani d . 1 . . C
  H1B1 -0.100(4) 0.186(4) -0.2567(19) 0.091(11) Uiso d . 1 . . H
  H1B2 -0.142(4) 0.336(4) -0.2339(17) 0.084(11) Uiso d . 1 . . H
  C2B 0.0189(4) 0.2558(4) -0.17848(18) 0.0794(11) Uani d . 1 . . C
  H2B 0.046(3) 0.173(3) -0.1609(13) 0.050(8) Uiso d . 1 . . H
  C3B 0.1372(6) 0.3047(9) -0.2243(3) 0.152(2) Uani d . 1 . . C
  H3B1 0.1139 0.2891 -0.2735 0.28(4) Uiso calc R 1 . . H
  H3B2 0.1453 0.3976 -0.2180 0.15(3) Uiso calc R 1 . . H
  C4B 0.2646(7) 0.2486(13) -0.2103(8) 0.275(6) Uani d . 1 . . C
  H4B1 0.3337 0.2853 -0.2409 0.38(6) Uiso calc R 1 . . H
  H4B2 0.2590 0.1569 -0.2182 0.42(10) Uiso calc R 1 . . H
  H4B3 0.2896 0.2646 -0.1619 0.7(2) Uiso calc R 1 . . H
  O5B -0.2229(3) 0.1920(3) -0.17740(16) 0.0869(8) Uani d . 1 . . O
  H5B -0.275(6) 0.244(5) -0.148(3) 0.18(3) Uiso d . 1 . . H
  N6B 0.0030(2) 0.3316(2) -0.11269(13) 0.0594(7) Uani d . 1 . . N
  C7B -0.0334(3) 0.4625(3) -0.1098(2) 0.0749(10) Uani d . 1 . . C
  C8B -0.0397(4) 0.5018(4) -0.0342(2) 0.0822(11) Uani d . 1 . . C
  H8B1 -0.1303 0.5374 -0.0229 0.129(16) Uiso calc R 1 . . H
  H8B2 0.0307 0.5663 -0.0239 0.115(14) Uiso calc R 1 . . H
  C9B -0.0133(4) 0.3790(3) 0.00739(18) 0.0795(11) Uani d . 1 . . C
  H9B1 0.0616 0.3913 0.0411 0.056(8) Uiso calc R 1 . . H
  H9B2 -0.0962 0.3523 0.0327 0.088(12) Uiso calc R 1 . . H
  C10B 0.0256(3) 0.2818(3) -0.04687(17) 0.0610(8) Uani d . 1 . . C
  O11B -0.0529(3) 0.5277(3) -0.16153(15) 0.1077(9) Uani d . 1 . . O
  O12B 0.0690(3) 0.1722(2) -0.03613(12) 0.0799(7) Uani d . 1 . . O
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
  C1A 0.086(3) 0.104(3) 0.060(2) 0.004(3) -0.008(2) -0.018(2)
  C2A 0.058(2) 0.080(2) 0.0539(19) 0.0033(19) -0.0068(16) 0.0027(17)
  C3A 0.092(3) 0.117(4) 0.060(2) -0.007(3) 0.006(2) 0.015(2)
  C4A 0.115(4) 0.116(4) 0.088(3) -0.024(3) 0.001(3) 0.026(3)
  O5A 0.0808(18) 0.0859(17) 0.0770(17) -0.0097(14) -0.0228(15) 0.0010(15)
  N6A 0.0523(16) 0.0592(14) 0.0506(14) 0.0020(14) -0.0015(13) 0.0016(12)
  C7A 0.051(2) 0.065(2) 0.074(2) -0.0048(18) -0.0055(18) 0.0017(19)
  C8A 0.081(3) 0.067(2) 0.068(2) -0.019(2) -0.0219(19) 0.0141(19)
  C9A 0.109(3) 0.062(2) 0.058(2) -0.002(2) -0.004(2) -0.0006(16)
  C10A 0.071(2) 0.0446(17) 0.061(2) -0.0004(17) 0.0038(18) 0.0001(15)
  O11A 0.0631(15) 0.107(2) 0.0952(17) 0.0197(15) -0.0040(14) -0.0081(16)
  O12A 0.0793(17) 0.0770(17) 0.0857(17) 0.0202(14) 0.0082(14) -0.0021(14)
  C1B 0.097(3) 0.085(3) 0.059(2) 0.026(3) 0.004(2) -0.002(2)
  C2B 0.080(3) 0.090(3) 0.068(2) 0.024(2) 0.016(2) 0.014(2)
  C3B 0.110(5) 0.218(9) 0.128(5) 0.018(5) 0.067(4) 0.034(4)
  C4B 0.082(5) 0.314(16) 0.430(19) -0.041(7) 0.088(7) -0.068(11)
  O5B 0.0859(19) 0.0876(19) 0.0873(17) 0.0005(17) -0.0016(16) -0.0159(17)
  N6B 0.0565(15) 0.0546(15) 0.0672(16) 0.0005(13) 0.0028(14) 0.0102(13)
  C7B 0.063(2) 0.063(2) 0.099(3) -0.0059(18) 0.002(2) 0.021(2)
  C8B 0.068(3) 0.070(2) 0.109(3) 0.002(2) -0.007(2) -0.013(2)
  C9B 0.077(3) 0.085(3) 0.076(2) -0.010(2) 0.003(2) -0.010(2)
  C10B 0.056(2) 0.0576(19) 0.069(2) -0.0106(17) -0.0049(17) 0.0091(17)
  O11B 0.127(2) 0.0796(18) 0.117(2) 0.0012(17) -0.0002(19) 0.0412(17)
  O12B 0.0951(18) 0.0623(15) 0.0824(16) -0.0020(14) -0.0140(14) 0.0134(13)
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
  C1A O5A . 1.415(5) YES
  C1A C2A . 1.519(5) NO
  C1A H1A1 . 0.98(3) NO
  C1A H1A2 . 0.95(4) NO
  C2A N6A . 1.468(4) YES
  C2A C3A . 1.527(5) NO
  C2A H2A . 1.01(3) NO
  C3A C4A . 1.499(6) NO
  C3A H3A1 . 0.9700 NO
  C3A H3A2 . 0.9700 NO
  C4A H4A1 . 0.9600 NO
  C4A H4A2 . 0.9600 NO
  C4A H4A3 . 0.9600 NO
  O5A H5A . 0.96(5) NO
  N6A C10A . 1.375(4) YES
  N6A C7A . 1.383(4) YES
  C7A O11A . 1.208(4) NO
  C7A C8A . 1.487(4) NO
  C8A C9A . 1.517(5) NO
  C8A H8A1 . 0.9700 NO
  C8A H8A2 . 0.9700 NO
  C9A C10A . 1.485(4) NO
  C9A H9A1 . 0.9700 NO
  C9A H9A2 . 0.9700 NO
  C10A O12A . 1.213(4) YES
  C1B O5B . 1.405(5) YES
  C1B C2B . 1.506(5) NO
  C1B H1B1 . 0.99(4) NO
  C1B H1B2 . 0.98(4) NO
  C2B N6B . 1.477(4) YES
  C2B C3B . 1.517(6) NO
  C2B H2B . 0.95(3) NO
  C3B C4B . 1.382(10) NO
  C3B H3B1 . 0.9700 NO
  C3B H3B2 . 0.9700 NO
  C4B H4B1 . 0.9600 NO
  C4B H4B2 . 0.9600 NO
  C4B H4B3 . 0.9600 NO
  O5B H5B . 0.92(6) NO
  N6B C10B . 1.364(4) YES
  N6B C7B . 1.397(4) YES
  C7B O11B . 1.203(4) NO
  C7B C8B . 1.486(5) NO
  C8B C9B . 1.514(5) NO
  C8B H8B1 . 0.9700 NO
  C8B H8B2 . 0.9700 NO
  C9B C10B . 1.483(4) NO
  C9B H9B1 . 0.9700 NO
  C9B H9B2 . 0.9700 NO
  C10B O12B . 1.223(3) YES