#------------------------------------------------------------------------------ #$Date: 2008-01-27 14:50:57 +0000 (Sun, 27 Jan 2008) $ #$Revision: 30 $ #$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_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_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_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_meas 'not measured' _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_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_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 _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_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 _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) ?