#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228422.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_2228422
loop_
_publ_author_name
'Liu, Shang-Yuan'
'Xu, Hai-Zhen'
'Zhu, You-Quan'
_publ_section_title
;
 (Z)-3-[(4-Ethoxyphenyl)(hydroxy)methylidene]-1-isopropylpyrrolidine-2,4-dione
;
_journal_coeditor_code           IS2629
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3202
_journal_paper_doi               10.1107/S1600536810046465
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H19 N O4'
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_chemical_name_systematic
;
(Z)-3-[(4-Ethoxyphenyl)(hydroxy)methylidene]-1-isopropylpyrrolidine-2,4-
dione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.581(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3390(15)
_cell_length_b                   5.3830(8)
_cell_length_c                   12.0490(18)
_cell_measurement_reflns_used    2865
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.80
_cell_volume                     735.16(18)
_computing_cell_refinement       'CrystalClear (Rigaku, 2009)'
_computing_data_collection       'CrystalClear (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku, 2009)'
_computing_molecular_graphics    'CrystalStructure (Rigaku, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9386
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0320
_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/[σ²(Fo²)+(0.0468P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                1668
_reflns_number_total             1933
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2629.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228422
_cod_database_fobs_code          2228422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_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
O O1 0.70417(9) 0.6075(2) 0.35972(9) 0.0257(3) Uani d . 1 . .
H H1A 0.7435 0.6020 0.3017 0.039 Uiso calc R 1 . .
O O2 0.84775(9) 0.4899(2) 0.21845(9) 0.0251(3) Uani d . 1 . .
O O3 0.89526(9) -0.0316(2) 0.53336(9) 0.0251(3) Uani d . 1 . .
O O4 0.48151(10) 0.4135(3) 0.82015(9) 0.0299(3) Uani d . 1 . .
N N1 0.96813(11) 0.1603(3) 0.26539(10) 0.0203(3) Uani d . 1 . .
C C1 0.74116(13) 0.4313(3) 0.42897(13) 0.0193(3) Uani d . 1 . .
C C2 0.83157(13) 0.2766(3) 0.39424(13) 0.0186(3) Uani d . 1 . .
C C3 0.88176(13) 0.3211(3) 0.28521(13) 0.0192(3) Uani d . 1 . .
C C4 0.99039(13) -0.0049(3) 0.35867(12) 0.0204(3) Uani d . 1 . .
H H4A 1.0717 0.0165 0.3892 0.024 Uiso calc R 1 . .
H H4B 0.9791 -0.1805 0.3364 0.024 Uiso calc R 1 . .
C C5 0.89965(13) 0.0726(3) 0.44344(13) 0.0192(4) Uani d . 1 . .
C C6 0.67596(12) 0.4261(3) 0.53246(13) 0.0188(3) Uani d . 1 . .
C C7 0.59784(13) 0.6206(3) 0.55394(13) 0.0220(4) Uani d . 1 . .
H H7 0.5904 0.7537 0.5024 0.026 Uiso calc R 1 . .
C C8 0.53130(13) 0.6236(3) 0.64833(13) 0.0233(4) Uani d . 1 . .
H H8 0.4786 0.7570 0.6612 0.028 Uiso calc R 1 . .
C C9 0.54203(13) 0.4304(4) 0.72421(13) 0.0227(4) Uani d . 1 . .
C C10 0.61937(14) 0.2358(3) 0.70400(14) 0.0248(4) Uani d . 1 . .
H H10 0.6266 0.1029 0.7556 0.030 Uiso calc R 1 . .
C C11 0.68552(14) 0.2340(3) 0.60987(14) 0.0236(4) Uani d . 1 . .
H H11 0.7383 0.1004 0.5975 0.028 Uiso calc R 1 . .
C C12 0.39293(16) 0.5968(4) 0.83947(16) 0.0361(5) Uani d . 1 . .
H H12A 0.3344 0.6001 0.7769 0.043 Uiso calc R 1 . .
H H12B 0.4292 0.7635 0.8466 0.043 Uiso calc R 1 . .
C C13 0.3340(2) 0.5264(5) 0.94565(16) 0.0554(7) Uani d . 1 . .
H H13A 0.2992 0.3605 0.9377 0.067 Uiso calc R 1 . .
H H13B 0.2719 0.6472 0.9612 0.067 Uiso calc R 1 . .
H H13C 0.3926 0.5258 1.0070 0.067 Uiso calc R 1 . .
C C14 1.04354(13) 0.1741(3) 0.16876(13) 0.0222(4) Uani d . 1 . .
H H14 1.0084 0.2990 0.1160 0.027 Uiso calc R 1 . .
C C15 1.16687(15) 0.2627(5) 0.20292(15) 0.0356(5) Uani d . 1 . .
H H15A 1.1614 0.4220 0.2418 0.043 Uiso calc R 1 . .
H H15B 1.2141 0.2834 0.1366 0.043 Uiso calc R 1 . .
H H15C 1.2045 0.1397 0.2523 0.043 Uiso calc R 1 . .
C C16 1.0475(2) -0.0729(5) 0.10959(16) 0.0481(6) Uani d . 1 . .
H H16A 1.0895 -0.1942 0.1567 0.058 Uiso calc R 1 . .
H H16B 1.0888 -0.0536 0.0397 0.058 Uiso calc R 1 . .
H H16C 0.9669 -0.1313 0.0939 0.058 Uiso calc R 1 . .
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
C1 O1 H1A . . 109.5 no
C9 O4 C12 . . 117.63(14) no
C3 N1 C4 . . 111.86(12) no
C3 N1 C14 . . 123.82(14) no
C4 N1 C14 . . 123.67(12) no
O1 C1 C2 . . 117.49(14) no
O1 C1 C6 . . 113.02(13) no
C2 C1 C6 . . 129.47(14) no
C1 C2 C5 . . 135.48(14) no
C1 C2 C3 . . 118.59(14) no
C5 C2 C3 . . 105.84(13) no
O2 C3 N1 . . 124.35(14) no
O2 C3 C2 . . 124.57(14) no
N1 C3 C2 . . 111.08(13) no
N1 C4 C5 . . 104.16(13) no
N1 C4 H4A . . 110.9 no
C5 C4 H4A . . 110.9 no
N1 C4 H4B . . 110.9 no
C5 C4 H4B . . 110.9 no
H4A C4 H4B . . 108.9 no
O3 C5 C2 . . 132.20(15) no
O3 C5 C4 . . 120.79(15) no
C2 C5 C4 . . 107.01(13) no
C11 C6 C7 . . 117.94(15) no
C11 C6 C1 . . 123.43(14) no
C7 C6 C1 . . 118.61(14) no
C8 C7 C6 . . 121.55(16) no
C8 C7 H7 . . 119.2 no
C6 C7 H7 . . 119.2 no
C7 C8 C9 . . 119.57(16) no
C7 C8 H8 . . 120.2 no
C9 C8 H8 . . 120.2 no
O4 C9 C8 . . 124.84(15) no
O4 C9 C10 . . 115.63(15) no
C8 C9 C10 . . 119.53(15) no
C11 C10 C9 . . 120.63(16) no
C11 C10 H10 . . 119.7 no
C9 C10 H10 . . 119.7 no
C10 C11 C6 . . 120.77(16) no
C10 C11 H11 . . 119.6 no
C6 C11 H11 . . 119.6 no
O4 C12 C13 . . 107.10(18) no
O4 C12 H12A . . 110.3 no
C13 C12 H12A . . 110.3 no
O4 C12 H12B . . 110.3 no
C13 C12 H12B . . 110.3 no
H12A C12 H12B . . 108.5 no
C12 C13 H13A . . 109.5 no
C12 C13 H13B . . 109.5 no
H13A C13 H13B . . 109.5 no
C12 C13 H13C . . 109.5 no
H13A C13 H13C . . 109.5 no
H13B C13 H13C . . 109.5 no
N1 C14 C16 . . 110.85(14) no
N1 C14 C15 . . 110.65(12) no
C16 C14 C15 . . 111.34(16) no
N1 C14 H14 . . 108.0 no
C16 C14 H14 . . 108.0 no
C15 C14 H14 . . 108.0 no
C14 C15 H15A . . 109.5 no
C14 C15 H15B . . 109.5 no
H15A C15 H15B . . 109.5 no
C14 C15 H15C . . 109.5 no
H15A C15 H15C . . 109.5 no
H15B C15 H15C . . 109.5 no
C14 C16 H16A . . 109.5 no
C14 C16 H16B . . 109.5 no
H16A C16 H16B . . 109.5 no
C14 C16 H16C . . 109.5 no
H16A C16 H16C . . 109.5 no
H16B C16 H16C . . 109.5 no
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
O1 C1 . 1.324(2) n
O1 H1A . 0.8400 no
O2 C3 . 1.2665(19) n
O3 C5 . 1.2222(19) n
O4 C9 . 1.3635(18) no
O4 C12 . 1.432(2) no
N1 C3 . 1.334(2) no
N1 C4 . 1.450(2) no
N1 C14 . 1.4654(18) no
C1 C2 . 1.394(2) n
C1 C6 . 1.467(2) no
C2 C5 . 1.459(2) no
C2 C3 . 1.466(2) n
C4 C5 . 1.528(2) no
C4 H4A . 0.9900 no
C4 H4B . 0.9900 no
C6 C11 . 1.395(2) no
C6 C7 . 1.400(2) no
C7 C8 . 1.382(2) no
C7 H7 . 0.9500 no
C8 C9 . 1.388(2) no
C8 H8 . 0.9500 no
C9 C10 . 1.392(2) no
C10 C11 . 1.377(2) no
C10 H10 . 0.9500 no
C11 H11 . 0.9500 no
C12 C13 . 1.508(3) no
C12 H12A . 0.9900 no
C12 H12B . 0.9900 no
C13 H13A . 0.9800 no
C13 H13B . 0.9800 no
C13 H13C . 0.9800 no
C14 C16 . 1.510(3) no
C14 C15 . 1.523(2) no
C14 H14 . 1.0000 no
C15 H15A . 0.9800 no
C15 H15B . 0.9800 no
C15 H15C . 0.9800 no
C16 H16A . 0.9800 no
C16 H16B . 0.9800 no
C16 H16C . 0.9800 no
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
O1 H1A O2 . 0.84 1.68 2.4701(16) 155
C11 H11 O3 . 0.95 2.08 2.945(2) 150
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 C5 . . . . 177.26(17) no
C6 C1 C2 C5 . . . . -4.6(3) no
O1 C1 C2 C3 . . . . 1.3(2) no
C6 C1 C2 C3 . . . . 179.52(15) no
C4 N1 C3 O2 . . . . 177.77(14) no
C14 N1 C3 O2 . . . . 6.7(2) no
C4 N1 C3 C2 . . . . -2.23(18) no
C14 N1 C3 C2 . . . . -173.26(13) no
C1 C2 C3 O2 . . . . -1.0(2) no
C5 C2 C3 O2 . . . . -178.00(14) no
C1 C2 C3 N1 . . . . 179.02(14) no
C5 C2 C3 N1 . . . . 2.00(17) no
C3 N1 C4 C5 . . . . 1.48(17) no
C14 N1 C4 C5 . . . . 172.53(14) no
C1 C2 C5 O3 . . . . 2.1(3) no
C3 C2 C5 O3 . . . . 178.34(17) no
C1 C2 C5 C4 . . . . -177.28(17) no
C3 C2 C5 C4 . . . . -1.00(16) no
N1 C4 C5 O3 . . . . -179.62(14) no
N1 C4 C5 C2 . . . . -0.19(16) no
O1 C1 C6 C11 . . . . 169.26(14) no
C2 C1 C6 C11 . . . . -9.0(2) no
O1 C1 C6 C7 . . . . -9.19(19) no
C2 C1 C6 C7 . . . . 172.57(16) no
C11 C6 C7 C8 . . . . -0.3(2) no
C1 C6 C7 C8 . . . . 178.19(14) no
C6 C7 C8 C9 . . . . 0.3(2) no
C12 O4 C9 C8 . . . . 5.8(2) no
C12 O4 C9 C10 . . . . -174.26(16) no
C7 C8 C9 O4 . . . . 179.75(15) no
C7 C8 C9 C10 . . . . -0.2(2) no
O4 C9 C10 C11 . . . . -179.68(14) no
C8 C9 C10 C11 . . . . 0.3(2) no
C9 C10 C11 C6 . . . . -0.4(2) no
C7 C6 C11 C10 . . . . 0.4(2) no
C1 C6 C11 C10 . . . . -178.04(14) no
C9 O4 C12 C13 . . . . 176.02(16) no
C3 N1 C14 C16 . . . . -129.11(18) no
C4 N1 C14 C16 . . . . 60.9(2) no
C3 N1 C14 C15 . . . . 106.86(18) no
C4 N1 C14 C15 . . . . -63.1(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656368
