#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/40/2214044.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_2214044
loop_
_publ_author_name
'Mutikainen, Ilpo'
'Kiriazis, Alexandros'
'Leikoski, Tuomo'
'Yli-Kauhaluoma, Jari'
_publ_section_title
;
 2-Ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindole-4-carboxylic
 acid
;
_journal_coeditor_code           BG2064
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3240
_journal_page_last               o3240
_journal_paper_doi               10.1107/S1600536807027900
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H13 N O4'
_chemical_formula_moiety         'C11 H13 N O4'
_chemical_formula_sum            'C11 H13 N O4'
_chemical_formula_weight         223.22
_chemical_name_systematic
;2-Ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindole-4-carboxylic
 acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 94.07(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4320(10)
_cell_length_b                   8.5880(10)
_cell_length_c                   14.342(2)
_cell_measurement_reflns_used    257
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      17.86
_cell_measurement_theta_min      2.17
_cell_volume                     1035.9(2)
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'EVAL (Nonius, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω
_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  0.0776
_diffrn_reflns_av_sigmaI/netI    0.1069
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7378
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         5.32
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0558
_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)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                1345
_reflns_number_total             2350
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2064.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214044
_cod_database_fobs_code          2214044
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
O O1 1.20615(19) 0.12766(19) 0.18956(12) 0.0291(5) Uani d . 1
H H1A 1.305(3) 0.108(3) 0.2114(19) 0.040(8) Uiso d . 1
O O2 1.20296(19) -0.1224(2) 0.14398(13) 0.0344(5) Uani d . 1
O O3 1.01229(17) -0.02571(19) 0.33666(12) 0.0275(4) Uani d . 1
O O4 0.48321(17) 0.0661(2) 0.28732(12) 0.0337(5) Uani d . 1
N N1 0.74206(19) 0.0088(2) 0.33060(13) 0.0191(5) Uani d . 1
C C1 1.1350(3) 0.0004(3) 0.15529(17) 0.0230(6) Uani d . 1
C C2 0.9591(2) 0.0274(3) 0.12836(17) 0.0208(5) Uani d . 1
H H2A 0.9518 0.0958 0.0718 0.025 Uiso calc R 1
C C3 0.8682(3) -0.1201(3) 0.10316(16) 0.0244(6) Uani d . 1
H H3A 0.9225 -0.2159 0.0965 0.029 Uiso calc R 1
C C4 0.7109(3) -0.1129(3) 0.09050(17) 0.0271(6) Uani d . 1
H H4A 0.6509 -0.2048 0.0771 0.032 Uiso calc R 1
C C5 0.6282(3) 0.0415(3) 0.09743(17) 0.0272(6) Uani d . 1
H H5A 0.5127 0.0242 0.1009 0.033 Uiso calc R 1
H H5B 0.6436 0.1039 0.0408 0.033 Uiso calc R 1
C C6 0.6941(2) 0.1316(3) 0.18465(16) 0.0208(5) Uani d . 1
H H6A 0.6670 0.2445 0.1772 0.025 Uiso calc R 1
C C7 0.8756(2) 0.1135(3) 0.20590(15) 0.0184(5) Uani d . 1
H H7A 0.9244 0.2190 0.2154 0.022 Uiso calc R 1
C C8 0.8919(2) 0.0247(3) 0.29702(16) 0.0187(5) Uani d . 1
C C9 0.6239(2) 0.0690(3) 0.27090(16) 0.0216(5) Uani d . 1
C C10 0.7154(3) -0.0611(3) 0.42150(17) 0.0251(6) Uani d . 1
H H10A 0.8034 -0.1338 0.4396 0.030 Uiso calc R 1
H H10B 0.6151 -0.1214 0.4164 0.030 Uiso calc R 1
C C11 0.7061(3) 0.0629(3) 0.49656(18) 0.0313(6) Uani d . 1
H H11A 0.6884 0.0130 0.5564 0.047 Uiso calc R 1
H H11B 0.6180 0.1340 0.4793 0.047 Uiso calc R 1
H H11C 0.8061 0.1215 0.5024 0.047 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'
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'
H H 0.0000 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
C1 O1 H1A 111.1(18)
C9 N1 C8 112.67(19)
C9 N1 C10 124.08(17)
C8 N1 C10 123.24(18)
O2 C1 O1 124.0(2)
O2 C1 C2 123.9(2)
O1 C1 C2 112.1(2)
C3 C2 C1 113.65(19)
C3 C2 C7 108.91(17)
C1 C2 C7 112.04(18)
C3 C2 H2A 107.3
C1 C2 H2A 107.3
C7 C2 H2A 107.3
C4 C3 C2 118.6(2)
C4 C3 H3A 120.7
C2 C3 H3A 120.7
C3 C4 C5 119.7(2)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
C4 C5 C6 110.73(19)
C4 C5 H5A 109.5
C6 C5 H5A 109.5
C4 C5 H5B 109.5
C6 C5 H5B 109.5
H5A C5 H5B 108.1
C9 C6 C5 110.30(18)
C9 C6 C7 104.05(18)
C5 C6 C7 113.84(17)
C9 C6 H6A 109.5
C5 C6 H6A 109.5
C7 C6 H6A 109.5
C8 C7 C2 111.26(18)
C8 C7 C6 104.42(17)
C2 C7 C6 113.64(18)
C8 C7 H7A 109.1
C2 C7 H7A 109.1
C6 C7 H7A 109.1
O3 C8 N1 123.7(2)
O3 C8 C7 127.59(19)
N1 C8 C7 108.66(18)
O4 C9 N1 122.9(2)
O4 C9 C6 127.3(2)
N1 C9 C6 109.74(17)
N1 C10 C11 111.22(19)
N1 C10 H10A 109.4
C11 C10 H10A 109.4
N1 C10 H10B 109.4
C11 C10 H10B 109.4
H10A C10 H10B 108.0
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.325(3)
O1 H1A 0.89(3)
O2 C1 1.217(3)
O3 C8 1.208(3)
O4 C9 1.226(2)
N1 C9 1.368(3)
N1 C8 1.391(3)
N1 C10 1.467(3)
C1 C2 1.523(3)
C2 C3 1.511(3)
C2 C7 1.546(3)
C2 H2A 1.0000
C3 C4 1.327(3)
C3 H3A 0.9500
C4 C5 1.505(3)
C4 H4A 0.9500
C5 C6 1.541(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C9 1.508(3)
C6 C7 1.547(3)
C6 H6A 1.0000
C7 C8 1.511(3)
C7 H7A 1.0000
C10 C11 1.520(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
O1 H1A O4 1_655 0.89(3) 1.83(3) 2.690(2) 164(2)
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
O2 C1 C2 C3 11.0(3)
O1 C1 C2 C3 -171.04(19)
O2 C1 C2 C7 135.0(2)
O1 C1 C2 C7 -47.1(2)
C1 C2 C3 C4 171.3(2)
C7 C2 C3 C4 45.7(3)
C2 C3 C4 C5 2.6(3)
C3 C4 C5 C6 -46.2(3)
C4 C5 C6 C9 -78.7(2)
C4 C5 C6 C7 37.8(3)
C3 C2 C7 C8 68.7(2)
C1 C2 C7 C8 -57.9(2)
C3 C2 C7 C6 -48.8(2)
C1 C2 C7 C6 -175.39(19)
C9 C6 C7 C8 6.6(2)
C5 C6 C7 C8 -113.5(2)
C9 C6 C7 C2 128.0(2)
C5 C6 C7 C2 7.9(3)
C9 N1 C8 O3 -176.9(2)
C10 N1 C8 O3 4.7(3)
C9 N1 C8 C7 3.2(3)
C10 N1 C8 C7 -175.14(19)
C2 C7 C8 O3 51.0(3)
C6 C7 C8 O3 174.0(2)
C2 C7 C8 N1 -129.13(18)
C6 C7 C8 N1 -6.2(2)
C8 N1 C9 O4 179.7(2)
C10 N1 C9 O4 -2.0(3)
C8 N1 C9 C6 1.3(3)
C10 N1 C9 C6 179.67(19)
C5 C6 C9 O4 -60.9(3)
C7 C6 C9 O4 176.6(2)
C5 C6 C9 N1 117.4(2)
C7 C6 C9 N1 -5.1(2)
C9 N1 C10 C11 -82.9(3)
C8 N1 C10 C11 95.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 131856954
