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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic     ?
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H11 N O3'
_chemical_formula_sum     'C12 H11 N O3'
_chemical_formula_weight     217.22
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     P-1
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.5984(5)
_cell_length_b     7.1839(4)
_cell_length_c     11.2817(6)
_cell_angle_alpha     103.084(4)
_cell_angle_beta     98.380(5)
_cell_angle_gamma     102.485(5)
_cell_volume     497.81(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     8.65
_cell_measurement_theta_max     15.35
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max      .5
_exptl_crystal_size_mid      .5
_exptl_crystal_size_min      .08
_exptl_crystal_density_diffrn     1.449
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     228
_exptl_absorpt_coefficient_mu      .105
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details     ?
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius CAD4'
_diffrn_measurement_method     'ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4924
_diffrn_reflns_av_R_equivalents      .0677
_diffrn_reflns_av_sigmaI/netI      .0710
_diffrn_reflns_theta_min     1.89
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max      .999
_diffrn_measured_fraction_theta_full      .999
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     <1
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2279
_reflns_number_gt     1652
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0677
_refine_ls_R_factor_gt      .0439
_refine_ls_wR_factor_ref      .1155
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     2279
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0494P)²+0.0415P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .269
_refine_diff_density_min      -.221
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
                          'Locally modified CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement     'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction     'HELENA (Spek, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2000)'
_computing_publication_material     'PLATON'
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  .47500(18)  .2735(2)  .03260(12)  .0184(3) Uani d . 1 . . N
    O1  .64505(18)  .0406(2)  -.30332(12)  .0297(3) Uani d . 1 . . O
    H1  .740(4)  .123(5)  -.225(3)  .087(10) Uiso d . 1 . . H
    O2  .76248(17)  .25770(19)  -.06444(12)  .0273(3) Uani d . 1 . . O
    O3  .02648(17)  -.02524(19)  -.19521(12)  .0286(3) Uani d . 1 . . O
    C1  .2841(3)  -.1079(3)  -.39485(17)  .0255(4) Uani d . 1 . . C
    H1A  .3238  -.0745  -.4694  .038 Uiso calc R 1 . . H
    H1B  .1476  -.0796  -.3857  .038 Uiso calc R 1 . . H
    H1C  .2722  -.2487  -.4028  .038 Uiso calc R 1 . . H
    C2  .4485(2)  .0119(2)  -.28416(16)  .0194(3) Uani d . 1 . . C
    C3  .4062(2)  .0885(2)  -.17068(16)  .0186(3) Uani d . 1 . . C
    C4  .2024(2)  .0700(2)  -.13554(16)  .0206(4) Uani d . 1 . . C
    C5  .2429(2)  .1946(3)  -.00265(15)  .0207(4) Uani d . 1 . . C
    H5A  .1716  .3033  .0027  .025 Uiso calc R 1 . . H
    H5B  .1910  .1130  .0520  .025 Uiso calc R 1 . . H
    C6  .5700(2)  .2136(2)  -.06489(16)  .0187(3) Uani d . 1 . . C
    C7  .5727(2)  .3948(2)  .15333(15)  .0192(3) Uani d . 1 . . C
    C8  .4440(3)  .4370(3)  .23868(16)  .0226(4) Uani d . 1 . . C
    H8  .2947  .3836  .2148  .027 Uiso calc R 1 . . H
    C9  .5332(3)  .5563(3)  .35773(16)  .0268(4) Uani d . 1 . . C
    H9  .4440  .5847  .4146  .032 Uiso calc R 1 . . H
    C10  .7509(3)  .6351(3)  .39540(17)  .0280(4) Uani d . 1 . . C
    H10  .8112  .7170  .4772  .034 Uiso calc R 1 . . H
    C11  .8785(3)  .5917(3)  .31090(18)  .0284(4) Uani d . 1 . . C
    H11 1.0278  .6442  .3358  .034 Uiso calc R 1 . . H
    C12  .7925(2)  .4731(3)  .19057(16)  .0237(4) Uani d . 1 . . C
    H12  .8824  .4454  .1340  .028 Uiso calc R 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  .0135(6)  .0221(7)  .0179(7)  .0033(5)  .0032(5)  .0029(6)
    O1  .0202(6)  .0461(8)  .0228(7)  .0106(6)  .0068(5)  .0056(6)
    O2  .0152(5)  .0386(7)  .0246(7)  .0057(5)  .0049(5)  .0020(6)
    O3  .0174(6)  .0360(7)  .0248(7)  -.0004(5)  .0023(5)  .0016(6)
    C1  .0255(8)  .0258(9)  .0218(9)  .0058(7)  .0028(7)  .0017(7)
    C2  .0185(7)  .0207(8)  .0208(8)  .0079(6)  .0044(6)  .0063(7)
    C3  .0165(7)  .0192(8)  .0192(8)  .0045(6)  .0028(6)  .0042(7)
    C4  .0189(7)  .0213(8)  .0220(9)  .0048(6)  .0041(6)  .0068(7)
    C5  .0151(7)  .0249(9)  .0208(8)  .0031(6)  .0055(6)  .0044(7)
    C6  .0182(7)  .0205(8)  .0176(8)  .0054(6)  .0038(6)  .0054(7)
    C7  .0218(8)  .0178(8)  .0172(8)  .0050(6)  .0022(6)  .0046(7)
    C8  .0213(8)  .0254(9)  .0214(9)  .0073(7)  .0045(6)  .0058(7)
    C9  .0361(10)  .0270(9)  .0195(9)  .0121(8)  .0085(7)  .0048(8)
    C10  .0369(10)  .0240(9)  .0180(9)  .0060(8)  -.0018(7)  .0018(7)
    C11  .0250(8)  .0259(9)  .0281(10)  .0012(7)  -.0013(7)  .0042(8)
    C12  .0210(8)  .0249(9)  .0231(9)  .0046(7)  .0032(6)  .0046(7)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C5 . 1.4732(18) y
    N1 C6 . 1.375(2) y
    N1 C7 . 1.412(2) y
    O1 C2 . 1.3258(19) y
    O1 H1 .  .99(3) ?
    O2 C6 . 1.2398(18) y
    O3 C4 . 1.2205(19) y
    C1 C2 . 1.480(2) ?
    C1 H1A .  .9800 ?
    C1 H1B .  .9800 ?
    C1 H1C .  .9800 ?
    C2 C3 . 1.368(2) y
    C3 C4 . 1.444(2) y
    C3 C6 . 1.456(2) y
    C4 C5 . 1.514(2) ?
    C5 H5A .  .9900 ?
    C5 H5B .  .9900 ?
    C7 C8 . 1.399(2) ?
    C7 C12 . 1.400(2) ?
    C8 C9 . 1.384(2) ?
    C8 H8 .  .9500 ?
    C9 C10 . 1.387(2) ?
    C9 H9 .  .9500 ?
    C10 C11 . 1.388(3) ?
    C10 H10 .  .9500 ?
    C11 C12 . 1.390(2) ?
    C11 H11 .  .9500 ?
    C12 H12 .  .9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 N1 C7 . . 128.11(13) y
    C6 N1 C5 . . 111.22(13) y
    C7 N1 C5 . . 120.66(12) y
    C2 O1 H1 . . 107.4(17) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O1 C2 C3 . . 121.62(14) ?
    O1 C2 C1 . . 114.26(15) ?
    C3 C2 C1 . . 124.13(14) ?
    C2 C3 C4 . . 128.07(15) ?
    C2 C3 C6 . . 123.00(14) ?
    C4 C3 C6 . . 108.89(15) ?
    O3 C4 C3 . . 129.85(16) ?
    O3 C4 C5 . . 123.46(14) ?
    C3 C4 C5 . . 106.69(13) ?
    N1 C5 C4 . . 104.54(12) ?
    N1 C5 H5A . . 110.8 ?
    C4 C5 H5A . . 110.8 ?
    N1 C5 H5B . . 110.8 ?
    C4 C5 H5B . . 110.8 ?
    H5A C5 H5B . . 108.9 ?
    O2 C6 N1 . . 126.41(15) ?
    O2 C6 C3 . . 124.97(15) ?
    N1 C6 C3 . . 108.62(13) ?
    C8 C7 C12 . . 119.06(16) ?
    C8 C7 N1 . . 118.43(14) ?
    C12 C7 N1 . . 122.51(14) ?
    C9 C8 C7 . . 120.28(15) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    C8 C9 C10 . . 121.08(16) ?
    C8 C9 H9 . . 119.5 ?
    C10 C9 H9 . . 119.5 ?
    C9 C10 C11 . . 118.55(17) ?
    C9 C10 H10 . . 120.7 ?
    C11 C10 H10 . . 120.7 ?
    C10 C11 C12 . . 121.46(16) ?
    C10 C11 H11 . . 119.3 ?
    C12 C11 H11 . . 119.3 ?
    C11 C12 C7 . . 119.57(15) ?
    C11 C12 H12 . . 120.2 ?
    C7 C12 H12 . . 120.2 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C2 C3 C4 . . . . -179.90(16) ?
    C1 C2 C3 C4 . . . .  .2(3) ?
    O1 C2 C3 C6 . . . . 2.9(3) ?
    C1 C2 C3 C6 . . . . -176.99(16) ?
    C2 C3 C4 O3 . . . . 4.7(3) ?
    C6 C3 C4 O3 . . . . -177.83(17) ?
    C2 C3 C4 C5 . . . . -175.89(16) ?
    C6 C3 C4 C5 . . . . 1.60(18) ?
    C6 N1 C5 C4 . . . . 1.74(18) ?
    C7 N1 C5 C4 . . . . -178.52(14) ?
    O3 C4 C5 N1 . . . . 177.48(15) ?
    C3 C4 C5 N1 . . . . -1.99(17) ?
    C7 N1 C6 O2 . . . .  -.6(3) ?
    C5 N1 C6 O2 . . . . 179.08(16) ?
    C7 N1 C6 C3 . . . . 179.49(14) ?
    C5 N1 C6 C3 . . . .  -.81(18) ?
    C2 C3 C6 O2 . . . . -2.8(3) ?
    C4 C3 C6 O2 . . . . 179.58(16) ?
    C2 C3 C6 N1 . . . . 177.11(15) ?
    C4 C3 C6 N1 . . . .  -.54(18) ?
    C6 N1 C7 C8 . . . . -179.93(16) ?
    C5 N1 C7 C8 . . . .  .4(2) ?
    C6 N1 C7 C12 . . . .  -.2(3) ?
    C5 N1 C7 C12 . . . . -179.86(16) ?
    C12 C7 C8 C9 . . . .  .7(3) ?
    N1 C7 C8 C9 . . . . -179.58(15) ?
    C7 C8 C9 C10 . . . .  -.5(3) ?
    C8 C9 C10 C11 . . . .  -.1(3) ?
    C9 C10 C11 C12 . . . .  .4(3) ?
    C10 C11 C12 C7 . . . .  -.2(3) ?
    C8 C7 C12 C11 . . . .  -.3(3) ?
    N1 C7 C12 C11 . . . . 179.93(16) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O1 H1 O2 .  .99(3) 1.81(3) 2.6948(18) 147(2) y
    O1 H1 O3 1_655  .99(3) 2.38(3) 2.8155(18) 106(2) y
    C5 H5B O3 2  .99 2.41 3.328(2) 154 y
    C1 H1B O3 .  .98 2.38 3.043(2) 124 y
    C12 H12 O2 .  .95 2.26 2.898(2) 124 y
data_global
_journal_date_recd_electronic     2000-12-14
_journal_date_accepted     2000-12-19
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue      4
_journal_page_first     433
_journal_page_last     434
_journal_paper_category     FO
_publ_contact_author_name     'Dianne Ellis'
_publ_contact_author_address
;
 Bijvoet Center for Biomolecular Research
 Department of Crystal and Structural Chemistry
 Utrecht University
 Padualaan 8
 3584 CH Utrecht
 The Netherlands
;
_publ_contact_author_email     d.d.ellis@chem.uu.nl
_publ_contact_author_fax     '030 31 253 3940'
_publ_contact_author_phone     '030 31 253 2533'
_publ_section_title
;
1-Phenyl-3-(1-hydroxyethylidene)-pyrrolidine-2,4-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Ellis, Dianne D.'
;   Bijvoet Center for Biomolecular Research
    Department of Crystal and Structural Chemistry
    Utrecht University
    Padualaan 8
    3584 CH Utrecht
    The Netherlands
;
    'Spek, Anthony L.'
;   Bijvoet Center for Biomolecular Research
    Department of Crystal and Structural Chemistry
    Utrecht University
    Padualaan 8
    3584 CH Utrecht
    The Netherlands
;
