#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/99/2209939.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_2209939
loop_
_publ_author_name
'Brady, Fiona'
'Gallagher, John F.'
_publ_section_title
;
 (2S)-4-Methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic
 acid
;
_journal_coeditor_code           LH2126
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3348
_journal_page_last               o3350
_journal_paper_doi               10.1107/S160053680602647X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H17 N O3'
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_chemical_melting_point          486
_chemical_name_systematic
;
(2S)-4-Methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic 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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8790(5)
_cell_length_b                   12.5223(16)
_cell_length_c                   18.029(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      15.0
_cell_volume                     1327.3(3)
_computing_cell_refinement       'SET4 and CELDIM (Enraf--Nonius, 1992)'
_computing_data_collection       'CAD-4 (Enraf--Nonius, 1992)'
_computing_data_reduction
'DATRD2 in NRCVAX96 (Gabe et al.,  1989)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'NRCVAX96 and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_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       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.061
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2394
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.13
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1373
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0436
_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)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                889
_reflns_number_total             1373
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2126.cif
_cod_data_source_block           I
_cod_database_code               2209939
_cod_database_fobs_code          2209939
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_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_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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -6 -3
-1 -5 -4
-2 -3 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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_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_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
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 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) ?
