#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202554.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_2202554 loop_ _publ_author_name 'Thamotharan, S.' 'Parthasarathi, V.' 'Gupta, P.' 'Jindal, D. P.' 'Piplani, P.' 'Linden, Anthony' _publ_section_title ; 2-[(2-Oxopyrrolidin-1-yl)carbonylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione: an antiamnesic agent ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1012 _journal_page_last o1013 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C14 H12 N2 O4' _chemical_formula_moiety 'C14 H12 N2 O4' _chemical_formula_sum 'C14 H12 N2 O4' _chemical_formula_weight 272.26 _chemical_melting_point 473 _chemical_name_systematic ; 2-[(2-Oxopyrrolidin-1-yl)carbonylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.7480(2) _cell_length_b 8.32800(10) _cell_length_c 27.9084(4) _cell_measurement_reflns_used 2839 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 2.0 _cell_volume 2498.06(7) _computing_cell_refinement 'DENZO--SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_data_reduction 'DENZO--SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP-3 (Version 1.07; Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 160(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_source 'Nonius FR591 sealed tube generator' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 29914 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 2.39 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.173 _refine_diff_density_min -0.194 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2459 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0465 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.4733P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1097 _refine_ls_wR_factor_ref 0.1285 _reflns_number_gt 1620 _reflns_number_total 2459 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6202.cif _[local]_cod_data_source_block I _cod_database_code 2202554 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' 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 O1 -0.04618(14) 0.14043(17) 0.59049(5) 0.0458(4) Uani d . 1 O O3 0.27434(14) 0.49855(18) 0.58283(5) 0.0459(4) Uani d . 1 O O11 -0.01451(14) 0.48029(17) 0.66903(5) 0.0446(4) Uani d . 1 O O13 0.25931(14) 0.20034(18) 0.73247(5) 0.0481(4) Uani d . 1 O N2 0.11528(14) 0.32121(18) 0.59882(5) 0.0316(4) Uani d . 1 N N12 0.08877(15) 0.37071(17) 0.73097(5) 0.0308(4) Uani d . 1 N C1 0.02859(18) 0.2310(2) 0.57284(7) 0.0332(5) Uani d . 1 C C3 0.18932(19) 0.4147(2) 0.56920(7) 0.0328(5) Uani d . 1 C C4 0.1863(2) 0.4463(3) 0.47650(7) 0.0423(5) Uani d . 1 C H4 0.2515 0.5231 0.4752 0.051 Uiso calc R 1 H C5 0.1286(2) 0.3916(3) 0.43516(7) 0.0488(6) Uani d . 1 C H5 0.1540 0.4328 0.4050 0.059 Uiso calc R 1 H C6 0.0350(2) 0.2784(3) 0.43711(8) 0.0486(6) Uani d . 1 C H6 -0.0022 0.2422 0.4082 0.058 Uiso calc R 1 H C7 -0.0060(2) 0.2164(3) 0.48057(7) 0.0427(5) Uani d . 1 C H7 -0.0703 0.1382 0.4819 0.051 Uiso calc R 1 H C8 0.05035(19) 0.2726(2) 0.52169(6) 0.0329(5) Uani d . 1 C C9 0.14500(18) 0.3841(2) 0.51966(6) 0.0325(5) Uani d . 1 C C10 0.14576(19) 0.2922(2) 0.64844(6) 0.0345(5) Uani d . 1 C H101 0.2345 0.3186 0.6538 0.041 Uiso calc R 1 H H102 0.1342 0.1767 0.6556 0.041 Uiso calc R 1 H C11 0.06652(18) 0.3901(2) 0.68244(7) 0.0325(5) Uani d . 1 C C13 0.18439(19) 0.2856(2) 0.75308(7) 0.0369(5) Uani d . 1 C C14 0.1779(2) 0.3192(3) 0.80590(7) 0.0461(6) Uani d . 1 C H141 0.2411 0.3996 0.8154 0.055 Uiso calc R 1 H H142 0.1912 0.2198 0.8247 0.055 Uiso calc R 1 H C15 0.0468(2) 0.3842(3) 0.81345(7) 0.0473(6) Uani d . 1 C H151 -0.0123 0.2963 0.8207 0.057 Uiso calc R 1 H H152 0.0449 0.4632 0.8399 0.057 Uiso calc R 1 H C16 0.0154(2) 0.4634(2) 0.76604(7) 0.0384(5) Uani d . 1 C H161 -0.0747 0.4557 0.7591 0.046 Uiso calc R 1 H H162 0.0402 0.5779 0.7660 0.046 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 O1 0.0429(9) 0.0496(9) 0.0450(9) -0.0089(8) -0.0024(7) 0.0101(7) O3 0.0514(10) 0.0470(9) 0.0394(9) -0.0128(8) -0.0014(7) -0.0051(7) O11 0.0486(9) 0.0499(9) 0.0352(9) 0.0154(8) -0.0018(7) 0.0027(7) O13 0.0457(9) 0.0581(9) 0.0405(9) 0.0131(8) -0.0038(7) 0.0012(7) N2 0.0375(10) 0.0346(9) 0.0228(9) -0.0010(8) 0.0002(7) 0.0002(7) N12 0.0390(9) 0.0301(8) 0.0233(9) 0.0015(8) 0.0002(7) 0.0004(7) C1 0.0342(11) 0.0327(11) 0.0327(11) 0.0026(9) -0.0023(9) 0.0009(9) C3 0.0385(12) 0.0297(10) 0.0302(11) 0.0024(9) 0.0018(9) -0.0028(9) C4 0.0486(13) 0.0461(13) 0.0322(12) 0.0052(11) 0.0062(10) 0.0033(10) C5 0.0617(16) 0.0573(14) 0.0275(12) 0.0177(13) 0.0019(11) 0.0030(10) C6 0.0585(15) 0.0562(14) 0.0310(12) 0.0165(13) -0.0097(11) -0.0104(11) C7 0.0475(13) 0.0435(12) 0.0370(12) 0.0064(10) -0.0102(10) -0.0083(10) C8 0.0383(11) 0.0324(11) 0.0280(11) 0.0069(9) -0.0028(9) -0.0029(8) C9 0.0397(11) 0.0318(10) 0.0260(11) 0.0053(9) 0.0007(9) -0.0010(8) C10 0.0391(11) 0.0389(11) 0.0254(11) 0.0029(9) -0.0025(9) 0.0004(9) C11 0.0347(11) 0.0328(10) 0.0302(11) -0.0007(10) -0.0002(9) 0.0020(9) C13 0.0392(12) 0.0351(11) 0.0366(12) -0.0025(10) 0.0007(10) -0.0002(10) C14 0.0574(14) 0.0510(13) 0.0299(12) -0.0032(12) -0.0063(10) 0.0010(10) C15 0.0654(15) 0.0459(13) 0.0305(12) 0.0023(12) 0.0042(11) -0.0025(10) C16 0.0461(13) 0.0344(11) 0.0346(12) 0.0002(10) 0.0070(10) -0.0046(9) 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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C3 N2 C1 112.00(16) C3 N2 C10 122.39(16) C1 N2 C10 123.94(15) C11 N12 C13 128.34(17) C11 N12 C16 119.70(15) C13 N12 C16 111.52(15) O1 C1 N2 124.56(18) O1 C1 C8 129.92(18) N2 C1 C8 105.52(16) O3 C3 N2 124.70(18) O3 C3 C9 129.32(18) N2 C3 C9 105.94(16) C9 C4 C5 117.2(2) C9 C4 H4 121.4 C5 C4 H4 121.4 C6 C5 C4 121.2(2) C6 C5 H5 119.4 C4 C5 H5 119.4 C5 C6 C7 121.3(2) C5 C6 H6 119.4 C7 C6 H6 119.4 C8 C7 C6 117.4(2) C8 C7 H7 121.3 C6 C7 H7 121.3 C9 C8 C7 121.24(18) C9 C8 C1 108.19(16) C7 C8 C1 130.56(19) C8 C9 C4 121.61(18) C8 C9 C3 108.32(16) C4 C9 C3 130.05(19) N2 C10 C11 112.54(16) N2 C10 H101 109.1 C11 C10 H101 109.1 N2 C10 H102 109.1 C11 C10 H102 109.1 H101 C10 H102 107.8 O11 C11 N12 119.97(17) O11 C11 C10 123.09(17) N12 C11 C10 116.93(16) O13 C13 N12 125.12(18) O13 C13 C14 127.08(19) N12 C13 C14 107.80(17) C13 C14 C15 104.18(17) C13 C14 H141 110.9 C15 C14 H141 110.9 C13 C14 H142 110.9 C15 C14 H142 110.9 H141 C14 H142 108.9 C16 C15 C14 103.84(17) C16 C15 H151 111.0 C14 C15 H151 111.0 C16 C15 H152 111.0 C14 C15 H152 111.0 H151 C15 H152 109.0 N12 C16 C15 103.45(16) N12 C16 H161 111.1 C15 C16 H161 111.1 N12 C16 H162 111.1 C15 C16 H162 111.1 H161 C16 H162 109.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.207(2) O3 C3 1.211(2) O11 C11 1.209(2) O13 C13 1.218(2) N2 C3 1.387(2) N2 C1 1.399(2) N2 C10 1.443(2) N12 C11 1.385(2) N12 C13 1.392(3) N12 C16 1.475(2) C1 C8 1.488(3) C3 C9 1.484(3) C4 C9 1.384(3) C4 C5 1.387(3) C4 H4 0.9500 C5 C6 1.380(3) C5 H5 0.9500 C6 C7 1.390(3) C6 H6 0.9500 C7 C8 1.380(3) C7 H7 0.9500 C8 C9 1.379(3) C10 C11 1.514(3) C10 H101 0.9900 C10 H102 0.9900 C13 C14 1.502(3) C14 C15 1.524(3) C14 H141 0.9900 C14 H142 0.9900 C15 C16 1.516(3) C15 H151 0.9900 C15 H152 0.9900 C16 H161 0.9900 C16 H162 0.9900 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 C15 H152 O1 3_556 0.99 2.44 3.426(3) 175 yes C16 H162 O13 6_665 0.99 2.56 3.261(3) 128 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 C3 N2 C1 O1 179.98(18) C10 N2 C1 O1 14.4(3) C3 N2 C1 C8 -0.2(2) C10 N2 C1 C8 -165.72(16) C1 N2 C3 O3 -176.99(18) C10 N2 C3 O3 -11.2(3) C1 N2 C3 C9 1.0(2) C10 N2 C3 C9 166.82(16) C9 C4 C5 C6 -0.8(3) C4 C5 C6 C7 0.8(3) C5 C6 C7 C8 0.2(3) C6 C7 C8 C9 -1.0(3) C6 C7 C8 C1 -179.83(19) O1 C1 C8 C9 179.0(2) N2 C1 C8 C9 -0.8(2) O1 C1 C8 C7 -2.1(4) N2 C1 C8 C7 178.08(19) C7 C8 C9 C4 1.0(3) C1 C8 C9 C4 -179.97(17) C7 C8 C9 C3 -177.60(17) C1 C8 C9 C3 1.4(2) C5 C4 C9 C8 0.0(3) C5 C4 C9 C3 178.21(19) O3 C3 C9 C8 176.3(2) N2 C3 C9 C8 -1.5(2) O3 C3 C9 C4 -2.1(4) N2 C3 C9 C4 -179.95(19) C3 N2 C10 C11 104.0(2) C1 N2 C10 C11 -91.9(2) C13 N12 C11 O11 -173.23(18) C16 N12 C11 O11 -1.5(3) C13 N12 C11 C10 7.9(3) C16 N12 C11 C10 179.58(16) N2 C10 C11 O11 1.2(3) N2 C10 C11 N12 -179.98(15) C11 N12 C13 O13 -7.2(3) C16 N12 C13 O13 -179.49(18) C11 N12 C13 C14 172.47(18) C16 N12 C13 C14 0.2(2) O13 C13 C14 C15 -162.0(2) N12 C13 C14 C15 18.3(2) C13 C14 C15 C16 -29.0(2) C11 N12 C16 C15 168.35(16) C13 N12 C16 C15 -18.6(2) C14 C15 C16 N12 28.8(2)