data_I _chemical_name_systematic ; (2S)-4-Methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid ; _chemical_name_common ? _chemical_formula_moiety 'C14 H17 N O3' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac 'C14 H17 N O3' _chemical_formula_weight 247.29 _chemical_melting_point 486 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 5.8790(5) _cell_length_b 12.5223(16) _cell_length_c 18.029(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1327.3(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.0 _cell_measurement_theta_max 25.0 _cell_measurement_temperature 294.0(10) _cell_special_details ; IR (\n~C\\db O~, cm^-1^): 1736, 1638 (KBr). ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? #Insert any special details here. ; _diffrn_ambient_temperature 294.0(10) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf--Nonius CAD-4' _diffrn_measurement_method '\w--2\q' _diffrn_reflns_number 2394 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.061 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% '1' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -6 -3 -1 -5 -4 -2 -3 4 _reflns_number_total 1373 _reflns_number_gt 889 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.0801 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 1.003 _refine_ls_number_reflns 1373 _refine_ls_number_parameters 185 _refine_ls_number_restraints 36 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.13 _refine_diff_density_min -0.13 _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 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' _computing_data_collection 'CAD-4 (Enraf--Nonius, 1992)' _computing_cell_refinement 'SET4 and CELDIM (Enraf--Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX96 (Gabe et al., 1989)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'NRCVAX96 and SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)' 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 O1A 0.648(3) 0.4641(5) 0.8185(5) 0.059(3) Uani d PDU 0.79(5) A 1 O O2A 0.667(4) 0.4445(9) 0.6954(4) 0.074(3) Uani d PDU 0.79(5) A 1 O O1B 0.582(8) 0.459(3) 0.807(2) 0.059(10) Uani d PDU 0.21(5) A 2 O O2B 0.752(8) 0.458(3) 0.7002(18) 0.066(10) Uani d PDU 0.21(5) A 2 O O3 0.5705(4) 0.14460(18) 0.70543(13) 0.0517(8) Uani d . 1 . . N N1 0.8834(5) 0.2520(2) 0.70881(13) 0.0380(7) Uani d . 1 . . C C1 0.7067(7) 0.4140(3) 0.75684(19) 0.0457(10) Uani d D 1 . . C C2 0.8176(6) 0.3080(2) 0.77582(16) 0.0392(9) Uani d D 1 A . C C3 0.7532(6) 0.1753(2) 0.67839(18) 0.0371(9) Uani d . 1 . . C C4 0.8679(6) 0.1403(2) 0.61054(17) 0.0370(9) Uani d . 1 . . C C5 0.8039(7) 0.0641(3) 0.55912(18) 0.0527(11) Uani d . 1 . . C C6 0.9450(8) 0.0476(3) 0.4992(2) 0.0605(12) Uani d . 1 . . C C7 1.1438(8) 0.1045(3) 0.4917(2) 0.0593(11) Uani d . 1 . . C C8 1.2086(6) 0.1802(3) 0.54341(18) 0.0495(10) Uani d . 1 . . C C9 1.0656(6) 0.1982(3) 0.60280(17) 0.0387(9) Uani d . 1 . . C C10 1.0864(6) 0.2761(2) 0.66548(17) 0.0432(9) Uani d . 1 . . C C11 1.0083(7) 0.3177(3) 0.83211(19) 0.0481(10) Uani d . 1 . . C C12 1.1179(8) 0.2129(3) 0.8559(2) 0.0552(11) Uani d . 1 A . C C13 1.2949(8) 0.2351(4) 0.9156(2) 0.0842(15) Uani d . 1 . . C C14 0.9461(8) 0.1313(3) 0.8821(2) 0.0753(13) Uani d . 1 . . H H1A 0.5976 0.5234 0.8082 0.071 Uiso calc PR 0.79(5) A 1 H H2A 0.4770 0.4909 0.7871 0.071 Uiso calc PR 0.21(5) A 2 H H2 0.6993 0.2643 0.7993 0.047 Uiso calc R 1 . . H H5 0.6701 0.0253 0.5648 0.063 Uiso calc R 1 . . H H6 0.9054 -0.0026 0.4635 0.073 Uiso calc R 1 . . H H7 1.2367 0.0917 0.4509 0.071 Uiso calc R 1 . . H H8 1.3442 0.2178 0.5383 0.059 Uiso calc R 1 . . H H10A 1.2239 0.2640 0.6940 0.052 Uiso calc R 1 . . H H10B 1.0850 0.3492 0.6477 0.052 Uiso calc R 1 . . H H11A 0.9490 0.3530 0.8759 0.058 Uiso calc R 1 A . H H11B 1.1256 0.3634 0.8114 0.058 Uiso calc R 1 . . H H12 1.1970 0.1830 0.8128 0.066 Uiso calc R 1 . . H H13A 1.4020 0.2869 0.8977 0.126 Uiso calc R 1 A . H H13B 1.3735 0.1702 0.9276 0.126 Uiso calc R 1 . . H H13C 1.2209 0.2622 0.9592 0.126 Uiso calc R 1 . . H H14A 0.8369 0.1185 0.8436 0.113 Uiso calc R 1 A . H H14B 0.8697 0.1578 0.9254 0.113 Uiso calc R 1 . . H H14C 1.0228 0.0658 0.8940 0.113 Uiso calc R 1 . . 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 O1A 0.079(6) 0.047(3) 0.051(3) 0.035(3) -0.012(4) -0.008(3) O2A 0.103(8) 0.075(4) 0.044(3) 0.039(4) -0.002(3) 0.006(3) O1B 0.045(16) 0.102(17) 0.031(11) 0.004(12) 0.013(12) 0.028(11) O2B 0.076(16) 0.061(11) 0.062(13) 0.013(11) 0.025(10) 0.027(10) O3 0.0407(17) 0.0489(15) 0.0655(17) -0.0112(14) 0.0112(15) -0.0048(13) N1 0.0326(17) 0.0406(15) 0.0408(16) -0.0046(16) 0.0052(15) -0.0090(14) C1 0.049(3) 0.045(2) 0.043(2) 0.001(2) 0.002(2) -0.003(2) C2 0.039(2) 0.0374(19) 0.0408(18) 0.000(2) 0.0040(19) -0.0032(17) C3 0.035(2) 0.0294(18) 0.047(2) -0.0018(19) -0.0004(19) 0.0021(16) C4 0.040(2) 0.0315(17) 0.0400(18) 0.005(2) 0.002(2) -0.0026(16) C5 0.059(3) 0.040(2) 0.059(2) -0.001(2) 0.001(2) -0.0060(19) C6 0.074(3) 0.052(2) 0.055(3) 0.007(3) 0.002(3) -0.020(2) C7 0.067(3) 0.060(2) 0.051(2) 0.015(3) 0.011(2) -0.010(2) C8 0.041(2) 0.056(2) 0.051(2) 0.003(2) 0.008(2) -0.001(2) C9 0.037(2) 0.0373(19) 0.0418(19) 0.003(2) 0.0011(19) -0.0009(17) C10 0.038(2) 0.044(2) 0.0479(19) -0.007(2) -0.002(2) -0.0012(16) C11 0.051(3) 0.045(2) 0.048(2) 0.009(2) -0.002(2) -0.0040(18) C12 0.059(3) 0.054(2) 0.053(2) 0.019(3) 0.005(2) 0.0045(19) C13 0.062(3) 0.117(4) 0.073(3) 0.021(3) -0.019(3) 0.015(3) C14 0.083(3) 0.062(3) 0.081(3) 0.011(3) 0.006(3) 0.018(2) _geom_special_details ; Mean plane data ex-SHELXL97 for molecule (I) ############################################ As detailed in the comment text section. ; 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 O1A C1 . 1.323(7) n O2A C1 . 1.194(7) n O3 C3 . 1.241(4) n N1 C2 . 1.449(4) n N1 C3 . 1.345(4) n N1 C10 . 1.458(4) n C1 C2 . 1.518(4) n C2 C11 . 1.517(4) n C3 C4 . 1.464(4) n C4 C9 . 1.377(5) n C4 C5 . 1.383(4) n C5 C6 . 1.377(5) n C6 C7 . 1.375(5) n C7 C8 . 1.384(4) n C8 C9 . 1.380(4) n C9 C10 . 1.498(4) n C11 C12 . 1.524(4) n C12 C14 . 1.513(5) n C12 C13 . 1.523(5) n O1B C1 . 1.292(19) n O2B C1 . 1.193(19) n O1A H1A . 0.8200 n O1B H2A . 0.8200 n C2 H2 . 0.9800 n C5 H5 . 0.9300 n C6 H6 . 0.9300 n C7 H7 . 0.9300 n C8 H8 . 0.9300 n C10 H10A . 0.9700 n C10 H10B . 0.9700 n C11 H11A . 0.9700 n C11 H11B . 0.9700 n C12 H12 . 0.9800 n C13 H13A . 0.9600 n C13 H13B . 0.9600 n C13 H13C . 0.9600 n C14 H14A . 0.9600 n C14 H14B . 0.9600 n C14 H14C . 0.9600 n 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 C2 N1 C3 . . 122.2(3) n C2 N1 C10 . . 124.4(3) n C3 N1 C10 . . 113.3(3) n O1A C1 O2A . . 125.2(6) n O1B C1 O2B . . 121.6(18) n O2A C1 C2 . . 124.9(5) n O2B C1 C2 . . 120.2(16) n O1A C1 C2 . . 109.8(5) n O1B C1 C2 . . 117.8(13) n N1 C2 C1 . . 110.5(3) n N1 C2 C11 . . 113.5(3) n C1 C2 C11 . . 113.4(3) n O3 C3 N1 . . 123.6(3) n O3 C3 C4 . . 129.4(3) n N1 C3 C4 . . 107.0(3) n C3 C4 C5 . . 129.9(3) n C3 C4 C9 . . 108.4(3) n C5 C4 C9 . . 121.7(3) n C4 C5 C6 . . 117.7(4) n C5 C6 C7 . . 120.8(4) n C6 C7 C8 . . 121.5(4) n C7 C8 C9 . . 117.8(3) n C4 C9 C8 . . 120.5(3) n C4 C9 C10 . . 109.6(3) n C8 C9 C10 . . 129.9(3) n N1 C10 C9 . . 101.7(3) n C2 C11 C12 . . 115.6(3) n C11 C12 C13 . . 109.3(3) n C11 C12 C14 . . 112.8(3) n C13 C12 C14 . . 111.0(3) n C1 O1A H1A . . 109.5 n C1 O1B H2A . . 109.5 n N1 C2 H2 . . 106.3 n C11 C2 H2 . . 106.3 n C1 C2 H2 . . 106.3 n C6 C5 H5 . . 121.1 n C4 C5 H5 . . 121.1 n C7 C6 H6 . . 119.6 n C5 C6 H6 . . 119.6 n C6 C7 H7 . . 119.3 n C8 C7 H7 . . 119.3 n C9 C8 H8 . . 121.1 n C7 C8 H8 . . 121.1 n N1 C10 H10A . . 111.4 n C9 C10 H10A . . 111.4 n N1 C10 H10B . . 111.4 n C9 C10 H10B . . 111.4 n H10A C10 H10B . . 109.3 n C2 C11 H11A . . 108.4 n C12 C11 H11A . . 108.4 n C2 C11 H11B . . 108.4 n C12 C11 H11B . . 108.4 n H11A C11 H11B . . 107.5 n C14 C12 H12 . . 107.8 n C13 C12 H12 . . 107.8 n C11 C12 H12 . . 107.8 n C12 C13 H13A . . 109.5 n C12 C13 H13B . . 109.5 n H13A C13 H13B . . 109.5 n C12 C13 H13C . . 109.5 n H13A C13 H13C . . 109.5 n H13B C13 H13C . . 109.5 n C12 C14 H14A . . 109.5 n C12 C14 H14B . . 109.5 n H14A C14 H14B . . 109.5 n C12 C14 H14C . . 109.5 n H14A C14 H14C . . 109.5 n H14B C14 H14C . . 109.5 n 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 C3 N1 C2 C11 . . . . 133.9(3) y C3 N1 C2 C1 . . . . -97.4(4) y O3 C3 N1 C2 . . . . -1.6(5) y O1A C1 C2 C11 . . . . -51.2(9) y C10 N1 C2 C11 . . . . -49.7(4) ? C10 N1 C2 C1 . . . . 79.0(4) ? O2B C1 C2 N1 . . . . -26(3) ? O2A C1 C2 N1 . . . . 4.0(14) ? O1B C1 C2 N1 . . . . 161(3) ? O1A C1 C2 N1 . . . . -179.9(8) n O2B C1 C2 C11 . . . . 102(3) ? O2A C1 C2 C11 . . . . 132.8(13) ? O1B C1 C2 C11 . . . . -71(3) ? C10 N1 C3 O3 . . . . -178.3(3) ? C2 N1 C3 C4 . . . . 177.8(3) ? C10 N1 C3 C4 . . . . 1.1(3) ? O3 C3 C4 C9 . . . . 179.4(3) ? N1 C3 C4 C9 . . . . 0.0(3) ? O3 C3 C4 C5 . . . . -0.2(6) ? N1 C3 C4 C5 . . . . -179.5(3) ? C9 C4 C5 C6 . . . . 0.0(5) ? C3 C4 C5 C6 . . . . 179.5(3) ? C4 C5 C6 C7 . . . . 0.7(5) ? C5 C6 C7 C8 . . . . -0.3(6) ? C6 C7 C8 C9 . . . . -0.8(5) ? C5 C4 C9 C8 . . . . -1.1(5) ? C3 C4 C9 C8 . . . . 179.3(3) ? C5 C4 C9 C10 . . . . 178.5(3) ? C3 C4 C9 C10 . . . . -1.1(4) ? C7 C8 C9 C4 . . . . 1.4(5) ? C7 C8 C9 C10 . . . . -178.0(3) ? C3 N1 C10 C9 . . . . -1.7(3) ? C2 N1 C10 C9 . . . . -178.3(3) ? C4 C9 C10 N1 . . . . 1.6(3) ? C8 C9 C10 N1 . . . . -178.9(3) ? N1 C2 C11 C12 . . . . -55.7(4) ? C1 C2 C11 C12 . . . . 177.2(3) ? C2 C11 C12 C14 . . . . -52.5(4) ? C2 C11 C12 C13 . . . . -176.5(3) ? 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 O1A H1A O3 3_656 0.82 1.83 2.634(9) 168 yes C10 H10A O3 1_655 0.97 2.54 3.366(4) 144 yes C8 H8 Cg1 2_556 0.93 2.74 3.473(4) 137 yes C2 H2 O3 . 0.98 2.38 2.812(4) 106 yes