#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203235.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_2203235
loop_
_publ_author_name
'You-Quan Zhu'
'Hai-Bin Song'
'Jian-Rong Li'
'Chang-Sheng Yao'
'Fang-Zhong Hu'
'Xiao-Mao Zou'
'Hua-Zheng Yang'
_publ_section_title
;
1-Benzyl-3-(\a-hydroxybenzylidene)pyrrolidine-2,4-dione
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o196
_journal_page_last             o198
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C18 H15 N O3'
_chemical_formula_moiety       'C18 H15 N O3'
_chemical_formula_sum          'C18 H15 N O3'
_chemical_formula_weight       293.31
_chemical_melting_point        ?
_chemical_name_systematic
1-Benzyl-3-(\a-hydroxybenzylidene)pyrrolidine-2,4-dione
_symmetry_cell_setting         Orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              90.00
_cell_angle_beta               90.00
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 5.569(3)
_cell_length_b                 15.062(7)
_cell_length_c                 18.245(9)
_cell_measurement_reflns_used  765
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    19.59
_cell_measurement_theta_min    2.61
_cell_volume                   1530.3(12)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_data_reduction      'SAINT (Bruker, 1999)'
_computing_molecular_graphics  'SHELXTL (Bruker, 1999)'
_computing_publication_material SHELXTL
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker SMART CCD area-detector'
_diffrn_measurement_method     '\f and \w'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0602
_diffrn_reflns_av_sigmaI/netI  0.0552
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_l_max     21
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_number          8033
_diffrn_reflns_theta_full      26.39
_diffrn_reflns_theta_max       26.39
_diffrn_reflns_theta_min       2.23
_diffrn_standards_decay_%      ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.087
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          Colourless
_exptl_crystal_density_diffrn  1.273
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_density_method  ?
_exptl_crystal_description     Prism
_exptl_crystal_F_000           616
_exptl_crystal_size_max        0.20
_exptl_crystal_size_mid        0.18
_exptl_crystal_size_min        0.16
_refine_diff_density_max       0.168
_refine_diff_density_min       -0.124
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.069
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   200
_refine_ls_number_reflns       1830
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.069
_refine_ls_R_factor_all        0.1120
_refine_ls_R_factor_gt         0.0593
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0612P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1132
_refine_ls_wR_factor_ref       0.1307
_reflns_number_gt              1101
_reflns_number_total           1830
_reflns_threshold_expression   I>2\s(I)
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'
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 0.4162(5) 0.93032(19) 0.50795(15) 0.0538(8) Uani d . 1 . . N
O1 0.0652(6) 0.8564(2) 0.69333(15) 0.0827(10) Uani d . 1 . . O
H1 0.0445 0.8981 0.6650 0.124 Uiso calc R 1 . . H
O2 0.1031(5) 0.96084(19) 0.58696(14) 0.0748(9) Uani d . 1 . . O
O3 0.6987(5) 0.7356(2) 0.57159(17) 0.0971(11) Uani d . 1 . . O
C1 0.2485(7) 0.8076(3) 0.67039(19) 0.0549(10) Uani d . 1 . . C
C2 0.2854(7) 0.7274(3) 0.71659(19) 0.0569(10) Uani d . 1 . . C
C3 0.1150(8) 0.7062(3) 0.7693(2) 0.0825(14) Uani d . 1 . . C
H3 -0.0187 0.7425 0.7749 0.099 Uiso calc R 1 . . H
C4 0.1397(10) 0.6317(4) 0.8139(3) 0.0948(16) Uani d . 1 . . C
H4 0.0225 0.6187 0.8486 0.114 Uiso calc R 1 . . H
C5 0.3339(10) 0.5779(4) 0.8070(3) 0.0899(16) Uani d . 1 . . C
H5 0.3480 0.5276 0.8362 0.108 Uiso calc R 1 . . H
C6 0.5088(11) 0.5978(4) 0.7572(3) 0.0977(17) Uani d . 1 . . C
H6 0.6438 0.5617 0.7534 0.117 Uiso calc R 1 . . H
C7 0.4859(9) 0.6726(3) 0.7114(2) 0.0854(15) Uani d . 1 . . C
H7 0.6056 0.6855 0.6775 0.102 Uiso calc R 1 . . H
C8 0.3718(6) 0.8355(2) 0.60767(18) 0.0468(9) Uani d . 1 . . C
C9 0.2828(6) 0.9146(3) 0.5680(2) 0.0512(9) Uani d . 1 . . C
C10 0.6063(7) 0.8650(3) 0.4991(2) 0.0593(10) Uani d . 1 . . C
H10A 0.7630 0.8931 0.5009 0.071 Uiso calc R 1 . . H
H10B 0.5902 0.8339 0.4528 0.071 Uiso calc R 1 . . H
C11 0.5726(7) 0.8011(3) 0.5638(2) 0.0585(10) Uani d . 1 . . C
C12 0.3516(7) 0.9935(3) 0.4494(2) 0.0672(11) Uani d . 1 . . C
H12A 0.2121 1.0274 0.4646 0.081 Uiso calc R 1 . . H
H12B 0.3085 0.9606 0.4056 0.081 Uiso calc R 1 . . H
C13 0.5537(7) 1.0570(2) 0.4312(2) 0.0558(10) Uani d . 1 . . C
C14 0.6461(9) 1.1135(3) 0.4836(2) 0.0789(13) Uani d . 1 . . C
H14 0.5838 1.1123 0.5309 0.095 Uiso calc R 1 . . H
C15 0.8302(9) 1.1720(3) 0.4669(3) 0.0902(15) Uani d . 1 . . C
H15 0.8895 1.2098 0.5029 0.108 Uiso calc R 1 . . H
C16 0.9255(9) 1.1746(3) 0.3977(3) 0.0869(14) Uani d . 1 . . C
H16 1.0484 1.2141 0.3866 0.104 Uiso calc R 1 . . H
C17 0.8380(10) 1.1183(4) 0.3452(3) 0.0973(17) Uani d . 1 . . C
H17 0.9020 1.1196 0.2981 0.117 Uiso calc R 1 . . H
C18 0.6546(9) 1.0595(4) 0.3618(2) 0.0853(15) Uani d . 1 . . C
H18 0.5983 1.0211 0.3257 0.102 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 0.0539(17) 0.0435(18) 0.0639(18) -0.0008(16) -0.0018(16) 0.0038(15)
O1 0.089(2) 0.080(2) 0.0790(19) 0.023(2) 0.0202(17) 0.0071(17)
O2 0.0816(19) 0.062(2) 0.0811(18) 0.0281(18) 0.0110(16) 0.0005(15)
O3 0.098(2) 0.073(2) 0.120(2) 0.044(2) 0.0348(19) 0.033(2)
C1 0.054(2) 0.051(2) 0.059(2) 0.001(2) -0.003(2) -0.010(2)
C2 0.060(2) 0.057(3) 0.053(2) -0.012(2) -0.009(2) 0.003(2)
C3 0.079(3) 0.081(4) 0.087(3) -0.004(3) 0.004(3) 0.016(3)
C4 0.093(4) 0.097(4) 0.094(3) -0.020(4) 0.009(3) 0.025(3)
C5 0.111(4) 0.077(4) 0.081(3) -0.025(4) -0.020(3) 0.027(3)
C6 0.109(4) 0.082(4) 0.102(3) 0.005(3) -0.004(3) 0.029(3)
C7 0.089(3) 0.084(4) 0.083(3) 0.010(3) 0.004(3) 0.026(3)
C8 0.052(2) 0.037(2) 0.0516(19) 0.0021(18) -0.0037(18) -0.0056(18)
C9 0.052(2) 0.040(2) 0.061(2) -0.0007(19) -0.005(2) -0.0107(19)
C10 0.048(2) 0.055(2) 0.075(2) -0.004(2) 0.004(2) 0.002(2)
C11 0.055(2) 0.044(2) 0.076(2) -0.002(2) -0.001(2) 0.001(2)
C12 0.067(3) 0.065(3) 0.069(2) -0.001(2) -0.012(2) 0.009(2)
C13 0.064(2) 0.043(2) 0.061(2) 0.012(2) -0.002(2) 0.010(2)
C14 0.107(4) 0.057(3) 0.072(3) -0.011(3) 0.013(3) -0.005(2)
C15 0.110(4) 0.054(3) 0.107(4) -0.023(3) 0.005(3) -0.006(3)
C16 0.085(3) 0.063(3) 0.113(4) -0.007(3) 0.015(3) 0.033(3)
C17 0.111(4) 0.106(4) 0.075(3) -0.015(4) 0.021(3) 0.020(3)
C18 0.105(4) 0.087(4) 0.064(3) -0.010(3) 0.000(3) 0.004(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C10 . . 111.9(3) Yes
C9 N1 C12 . . 124.7(3) Yes
C10 N1 C12 . . 122.2(3) Yes
C1 O1 H1 . . 109.5 Yes
O1 C1 C8 . . 118.0(3) Yes
O1 C1 C2 . . 112.2(3) Yes
C8 C1 C2 . . 129.8(4) Yes
C3 C2 C7 . . 117.3(4) Yes
C3 C2 C1 . . 119.1(4) ?
C7 C2 C1 . . 123.7(4) ?
C2 C3 C4 . . 121.6(5) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 120.3(5) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.0(5) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C7 . . 120.4(5) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C2 C7 C6 . . 120.5(4) ?
C2 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C1 C8 C11 . . 135.5(4) Yes
C1 C8 C9 . . 118.5(3) Yes
C11 C8 C9 . . 105.8(3) Yes
O2 C9 N1 . . 124.1(4) Yes
O2 C9 C8 . . 125.0(3) Yes
N1 C9 C8 . . 110.8(3) Yes
N1 C10 C11 . . 104.4(3) Yes
N1 C10 H10A . . 110.9 Yes
C11 C10 H10A . . 110.9 ?
N1 C10 H10B . . 110.9 ?
C11 C10 H10B . . 110.9 ?
H10A C10 H10B . . 108.9 ?
O3 C11 C8 . . 131.3(4) Yes
O3 C11 C10 . . 121.8(4) Yes
C8 C11 C10 . . 106.9(3) ?
N1 C12 C13 . . 112.6(3) ?
N1 C12 H12A . . 109.1 ?
C13 C12 H12A . . 109.1 ?
N1 C12 H12B . . 109.1 ?
C13 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C14 C13 C18 . . 117.7(4) ?
C14 C13 C12 . . 121.0(4) ?
C18 C13 C12 . . 121.2(4) ?
C13 C14 C15 . . 121.1(4) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C16 C15 C14 . . 120.5(5) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C17 C16 C15 . . 119.4(5) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C16 C17 C18 . . 120.3(5) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C13 . . 121.0(5) ?
C17 C18 H18 . . 119.5 ?
C13 C18 H18 . . 119.5 ?
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 C9 . 1.345(4) Yes
N1 C10 . 1.454(5) Yes
N1 C12 . 1.475(4) Yes
O1 C1 . 1.326(4) Yes
O1 H1 . 0.8200 ?
O2 C9 . 1.268(4) Yes
O3 C11 . 1.219(5) Yes
C1 C8 . 1.399(5) Yes
C1 C2 . 1.487(5) Yes
C2 C3 . 1.388(5) Yes
C2 C7 . 1.392(6) Yes
C3 C4 . 1.393(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.357(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.366(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.408(6) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C11 . 1.469(5) Yes
C8 C9 . 1.479(5) Yes
C10 C11 . 1.535(5) Yes
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.514(6) Yes
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.379(6) Yes
C13 C18 . 1.387(5) ?
C14 C15 . 1.386(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.369(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.369(7) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.386(7) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
C10 H10B O3 4_466 0.97 2.46 3.019(5) 116 Yes
O1 H1 O2 . 0.82 1.74 2.507(4) 155 Yes
C3 H3 O1 . 0.93 2.32 2.669(6) 102 Yes
C7 H7 O3 . 0.93 2.14 2.969(6) 148 Yes
C12 H12A O2 . 0.97 2.52 2.908(5) 104 Yes
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 C1 C2 C3 . . . . 8.6(5) Yes
C8 C1 C2 C3 . . . . -169.4(4) Yes
O1 C1 C2 C7 . . . . -169.8(4) Yes
C8 C1 C2 C7 . . . . 12.1(6) Yes
C7 C2 C3 C4 . . . . -1.7(6) ?
C1 C2 C3 C4 . . . . 179.7(4) Yes
C2 C3 C4 C5 . . . . 0.4(7) ?
C3 C4 C5 C6 . . . . 1.4(8) ?
C4 C5 C6 C7 . . . . -1.7(8) ?
C3 C2 C7 C6 . . . . 1.4(7) ?
C1 C2 C7 C6 . . . . 179.9(4) ?
C5 C6 C7 C2 . . . . 0.3(8) ?
O1 C1 C8 C11 . . . . -177.8(4) ?
C2 C1 C8 C11 . . . . 0.1(7) ?
O1 C1 C8 C9 . . . . -3.6(5) ?
C2 C1 C8 C9 . . . . 174.4(3) ?
C10 N1 C9 O2 . . . . -178.4(3) Yes
C12 N1 C9 O2 . . . . -10.5(5) Yes
C10 N1 C9 C8 . . . . 0.6(4) Yes
C12 N1 C9 C8 . . . . 168.5(3) Yes
C1 C8 C9 O2 . . . . 1.2(5) Yes
C11 C8 C9 O2 . . . . 177.0(3) Yes
C1 C8 C9 N1 . . . . -177.9(3) Yes
C11 C8 C9 N1 . . . . -2.1(4) Yes
C9 N1 C10 C11 . . . . 1.1(4) ?
C12 N1 C10 C11 . . . . -167.2(3) ?
C1 C8 C11 O3 . . . . -2.1(7) ?
C9 C8 C11 O3 . . . . -176.8(4) ?
C1 C8 C11 C10 . . . . 177.4(4) ?
C9 C8 C11 C10 . . . . 2.6(4) ?
N1 C10 C11 O3 . . . . 177.2(4) ?
N1 C10 C11 C8 . . . . -2.3(4) ?
C9 N1 C12 C13 . . . . 129.4(4) Yes
C10 N1 C12 C13 . . . . -63.9(4) Yes
N1 C12 C13 C14 . . . . -60.2(5) Yes
N1 C12 C13 C18 . . . . 118.9(4) Yes
C18 C13 C14 C15 . . . . 1.3(7) ?
C12 C13 C14 C15 . . . . -179.6(4) ?
C13 C14 C15 C16 . . . . -0.4(8) ?
C14 C15 C16 C17 . . . . -0.4(8) ?
C15 C16 C17 C18 . . . . 0.1(8) ?
C16 C17 C18 C13 . . . . 0.9(8) ?
C14 C13 C18 C17 . . . . -1.6(7) ?
C12 C13 C18 C17 . . . . 179.3(4) ?