#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011892.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011892
loop_
_publ_author_name
'Ellis, Dianne D.'
'Spek, Anthony L.'
_publ_section_title
;
 3-(1-Hydroxyethylidene)-1-phenylpyrrolidine-2,4-dione
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              433
_journal_page_last               434
_journal_paper_doi               10.1107/S0108270100020758
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C12 H11 N O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.084(4)
_cell_angle_beta                 98.380(5)
_cell_angle_gamma                102.485(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5984(5)
_cell_length_b                   7.1839(4)
_cell_length_c                   11.2817(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      15.35
_cell_measurement_theta_min      8.65
_cell_volume                     497.81(6)
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_collection
'Locally modified CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0677
_diffrn_reflns_av_sigmaI/netI    .0710
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4924
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .5
_exptl_crystal_size_min          .08
_refine_diff_density_max         .269
_refine_diff_density_min         -.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          .0677
_refine_ls_R_factor_gt           .0439
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0494P)²+0.0415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1155
_reflns_number_gt                1652
_reflns_number_total             2279
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            na1499.cif
_cod_data_source_block           I
_cod_original_cell_volume        497.81(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2011892
_cod_database_fobs_code          2011892
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_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_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
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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652318
