#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/06/2010697.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_2010697 loop_ _publ_author_name 'Gallagher, John F.' 'Brady, Fiona' 'Murphy, Carol' _publ_section_title ; Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 365 _journal_page_last 368 _journal_paper_doi 10.1107/S0108270199015619 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H13 N O4 ' _chemical_formula_sum 'C12 H13 N O4' _chemical_formula_weight 235.23 _chemical_melting_point 459 _chemical_name_systematic ; (2S/3R)-3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2209(6) _cell_length_b 11.9726(13) _cell_length_c 15.0705(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 19.61 _cell_measurement_theta_min 9.65 _cell_volume 1122.46(19) _computing_cell_refinement 'CAD-4-PC Software' _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_data_reduction 'NRCVAX96 (Gabe et al., 1989)' _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996), ORTEX (McArdle, 1995) and PLATON (Spek, 1998) ; _computing_publication_material 'NRCVAX96, SHELXL97 and PREP8 (Ferguson, 1998)' _computing_structure_refinement 'NRCVAX96 and SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .020 _diffrn_reflns_av_sigmaI/netI .046 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3932 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 'variation <1' _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .105 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_meas ? _exptl_crystal_description plate _exptl_crystal_F_000 496 _exptl_crystal_size_max .32 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .12 _refine_diff_density_max .16 _refine_diff_density_min -.15 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 'not reliably determined' _refine_ls_extinction_coef .011(3) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997a)' _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 1967 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.007 _refine_ls_R_factor_all .073 _refine_ls_R_factor_gt .040 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0538P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .096 _reflns_number_gt 1441 _reflns_number_total 1967 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1380.cif _[local]_cod_data_source_block I _[local]_cod_chemical_formula_sum_orig 'C12 H13 N O4 ' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1122.5(2) _cod_database_code 2010697 _cod_database_fobs_code 2010697 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' 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 O1 .5667(4) .22403(18) .98584(13) .0491(6) Uani d . 1 . . O O2 .5280(4) .37524(18) .90086(15) .0652(7) Uani d . 1 . . O O3 .2206(3) .18768(18) .71575(12) .0457(5) Uani d . 1 . . O O4 .9620(3) .1801(2) .86098(13) .0462(5) Uani d . 1 . . O N1 .5624(3) .24890(18) .74759(14) .0349(5) Uani d . 1 . . N C1 .5560(5) .2772(3) .90909(18) .0399(7) Uani d . 1 . . C C2 .5774(4) .1939(2) .83343(15) .0339(6) Uani d . 1 . . C C3 .3828(4) .2419(2) .69714(16) .0325(6) Uani d . 1 . . C C4 .4196(4) .3118(2) .61848(16) .0320(6) Uani d . 1 . . C C5 .2828(5) .3318(2) .54723(17) .0394(7) Uani d . 1 . . C C6 .3540(6) .4043(3) .48278(19) .0499(9) Uani d . 1 . . C C7 .5552(6) .4542(2) .48836(18) .0478(8) Uani d . 1 . . C C8 .6884(5) .4343(2) .55979(19) .0425(8) Uani d . 1 . . C C9 .6180(4) .3623(2) .62557(17) .0339(6) Uani d . 1 . . C C10 .7226(4) .3259(2) .71118(18) .0383(7) Uani d . 1 . . C C11 .7722(4) .1165(2) .84408(16) .0355(7) Uani d . 1 . . C C12 .7996(6) .0391(2) .76572(18) .0471(8) Uani d . 1 . . C H1 .542(7) .266(3) 1.027(3) .091(14) Uiso d . 1 . . H H4 1.047(6) .181(3) .820(2) .083(14) Uiso d . 1 . . H H2 .4508 .1455 .8375 .041 Uiso calc R 1 . . H H5 .1490 .2975 .5433 .047 Uiso calc R 1 . . H H6 .2658 .4203 .4346 .060 Uiso calc R 1 . . H H7 .6007 .5016 .4433 .057 Uiso calc R 1 . . H H8 .8224 .4684 .5637 .051 Uiso calc R 1 . . H H10A .8583 .2884 .7003 .046 Uiso calc R 1 . . H H10B .7465 .3888 .7505 .046 Uiso calc R 1 . . H H11 .7460 .0699 .8964 .043 Uiso calc R 1 . . H H12A .9228 -.0077 .7751 .071 Uiso calc R 1 . . H H12B .8198 .0824 .7127 .071 Uiso calc R 1 . . H H12C .6737 -.0066 .7595 .071 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 .0561(14) .0606(14) .0306(11) .0086(11) .0091(11) -.0019(10) O2 .091(2) .0475(13) .0569(14) .0125(13) .0100(13) .0000(11) O3 .0331(11) .0667(13) .0372(10) -.0122(12) -.0003(9) .0037(10) O4 .0330(11) .0746(14) .0309(11) -.0032(12) -.0020(10) -.0073(10) N1 .0261(12) .0471(13) .0313(11) -.0073(12) -.0022(10) .0094(10) C1 .0313(17) .0486(18) .0400(16) .0024(15) .0047(14) .0020(13) C2 .0321(16) .0435(15) .0261(13) -.0043(14) .0031(11) .0069(12) C3 .0276(15) .0430(16) .0269(13) -.0026(14) .0042(11) -.0039(12) C4 .0337(17) .0359(14) .0265(13) .0040(15) .0012(11) -.0025(11) C5 .0367(16) .0482(18) .0333(14) .0002(15) .0005(14) -.0069(13) C6 .066(2) .054(2) .0292(15) .0130(17) -.0045(15) .0001(14) C7 .068(2) .0421(17) .0333(15) .0057(18) .0108(17) .0065(13) C8 .0454(19) .0383(17) .0437(17) -.0049(14) .0106(15) .0052(13) C9 .0352(16) .0333(14) .0333(14) .0031(13) .0031(13) -.0007(12) C10 .0295(15) .0445(16) .0409(14) -.0063(15) .0015(14) .0074(13) C11 .0361(17) .0412(16) .0292(14) -.0022(14) .0030(12) .0058(12) C12 .051(2) .0486(18) .0422(17) .0009(16) .0075(15) -.0005(14) 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 1 7 2 3 4 3 5 0 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 C2 N1 C3 121.6(2) yes C2 N1 C10 125.1(2) yes C3 N1 C10 113.0(2) yes O1 C1 O2 124.9(3) yes O1 C1 C2 109.7(2) yes O2 C1 C2 125.4(3) yes N1 C2 C1 111.4(2) yes N1 C2 C11 114.7(2) yes C1 C2 C11 112.7(2) yes O3 C3 N1 125.5(2) yes O3 C3 C4 127.7(2) yes N1 C3 C4 106.8(2) yes C3 C4 C5 128.7(3) no C3 C4 C9 109.1(2) no C5 C4 C9 122.2(2) no C4 C5 C6 117.2(3) no C5 C6 C7 121.2(3) no C6 C7 C8 121.0(3) no C7 C8 C9 118.5(3) no C4 C9 C8 120.0(3) no C4 C9 C10 109.0(2) yes C8 C9 C10 131.0(3) yes N1 C10 C9 102.0(2) yes O4 C11 C2 110.5(2) yes O4 C11 C12 111.9(2) yes C2 C11 C12 112.2(2) yes 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 . 1.322(3) yes O2 C1 . 1.193(3) yes O3 C3 . 1.232(3) yes O4 C11 . 1.427(3) yes N1 C2 . 1.454(3) yes N1 C3 . 1.354(3) yes N1 C10 . 1.465(3) yes C1 C2 . 1.520(4) yes C2 C11 . 1.534(4) yes C3 C4 . 1.469(4) yes C4 C5 . 1.391(4) no C4 C9 . 1.379(4) no C5 C6 . 1.376(4) no C6 C7 . 1.389(4) no C7 C8 . 1.379(4) no C8 C9 . 1.384(4) no C9 C10 . 1.509(4) yes C11 C12 . 1.511(3) yes 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 O4 2_457 .81(4) 1.87(4) 2.659(3) 162(4) yes O4 H4 O3 1_655 .82(4) 1.90(4) 2.718(3) 174(4) yes C10 H10A O3 1_655 .97 2.57 3.513(4) 165 yes C5 H5 Cg2 2_456 .93 2.80 3.512(3) 134 yes C11 H11 Cg2 3_646 .98 2.77 3.573(3) 140 yes C12 H12C Cg1 3_646 .96 2.84 3.672(3) 145 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 C3 N1 C2 C1 -104.5(3) yes C10 N1 C2 C1 68.3(3) no C3 N1 C2 C11 125.9(3) no C10 N1 C2 C11 -61.3(3) no O2 C1 C2 N1 .8(4) yes O1 C1 C2 N1 178.9(2) no O2 C1 C2 C11 131.4(3) no O1 C1 C2 C11 -50.5(3) no C2 N1 C3 O3 -2.3(4) no C10 N1 C3 O3 -175.9(3) no C2 N1 C3 C4 176.8(2) no C10 N1 C3 C4 3.2(3) no O3 C3 C4 C9 176.9(3) no N1 C3 C4 C9 -2.2(3) no O3 C3 C4 C5 -.9(5) no N1 C3 C4 C5 -180.0(3) no C9 C4 C5 C6 .3(4) no C3 C4 C5 C6 177.9(3) no C4 C5 C6 C7 .8(4) no C5 C6 C7 C8 -1.4(4) no C6 C7 C8 C9 .7(4) no C5 C4 C9 C8 -1.0(4) no C3 C4 C9 C8 -179.0(2) no C5 C4 C9 C10 178.4(2) no C3 C4 C9 C10 .4(3) no C7 C8 C9 C4 .4(4) no C7 C8 C9 C10 -178.7(3) no C3 N1 C10 C9 -2.9(3) no C2 N1 C10 C9 -176.3(2) no C4 C9 C10 N1 1.4(3) no C8 C9 C10 N1 -179.3(3) no N1 C2 C11 O4 78.1(3) yes C1 C2 C11 O4 -50.8(3) yes N1 C2 C11 C12 -47.5(3) no C1 C2 C11 C12 -176.4(2) no