#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/07/2220744.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_2220744
loop_
_publ_author_name
'Hijji, Yousef M.'
'Benjamin, Ellis'
'Benjamin, Earl'
'Butcher, Ray J.'
'Jasinski, Jerry P.'
_publ_section_title
;
 3-(2,6-Dioxopiperidin-3-yl)-3-azabicyclo[3.2.0]heptane-2,4-dione
;
_journal_coeditor_code           CS2103
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o394
_journal_page_last               o395
_journal_paper_doi               10.1107/S1600536809002839
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H12 N2 O4'
_chemical_formula_moiety         'C11 H12 N2 O4'
_chemical_formula_sum            'C11 H12 N2 O4'
_chemical_formula_weight         236.23
_chemical_name_systematic
;
3-(2,6-Dioxopiperidin-3-yl)-3-azabicyclo[3.2.0]heptane-2,4-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 116.201(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7332(7)
_cell_length_b                   9.9358(5)
_cell_length_c                   11.0753(7)
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.5620
_cell_measurement_theta_min      4.8522
_cell_volume                     1059.74(13)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'φ and 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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10798
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.52
_diffrn_reflns_theta_min         4.86
_diffrn_standards_decay_%        2
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0386
_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)+(0.0607P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2193
_reflns_number_total             3496
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cs2103.cif
_cod_data_source_block           I
_cod_original_cell_volume        1059.75(13)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2220744
_cod_database_fobs_code          2220744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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 O1 0.32277(8) 0.13630(8) 0.42230(7) 0.0271(2) Uani d . 1 . .
O O2 0.04309(9) 0.50429(9) 0.26752(8) 0.0372(2) Uani d . 1 . .
O O3 0.02024(7) 0.12103(8) 0.39189(7) 0.02458(19) Uani d . 1 . .
O O4 0.16813(8) 0.16581(9) 0.83857(8) 0.0350(2) Uani d . 1 . .
N N1 0.18201(8) 0.32243(9) 0.37104(8) 0.0196(2) Uani d . 1 . .
N N2 0.10433(9) 0.14479(9) 0.61681(8) 0.0222(2) Uani d . 1 . .
H H2B 0.0683 0.0660 0.6195 0.027 Uiso calc R 1 . .
C C1 0.25634(10) 0.22276(11) 0.34235(10) 0.0211(2) Uani d . 1 . .
C C2 0.23146(11) 0.24120(12) 0.19918(11) 0.0258(3) Uani d . 1 . .
H H2A 0.3154 0.2315 0.1827 0.031 Uiso calc R 1 . .
C C3 0.09860(12) 0.16602(13) 0.09668(11) 0.0340(3) Uani d . 1 . .
H H3A 0.1154 0.1076 0.0330 0.041 Uiso calc R 1 . .
H H3B 0.0487 0.1164 0.1396 0.041 Uiso calc R 1 . .
C C4 0.03228(13) 0.30239(14) 0.03642(11) 0.0357(3) Uani d . 1 . .
H H4A -0.0594 0.3172 0.0355 0.043 Uiso calc R 1 . .
H H4B 0.0281 0.3205 -0.0532 0.043 Uiso calc R 1 . .
C C5 0.15349(12) 0.37539(12) 0.15340(11) 0.0278(3) Uani d . 1 . .
H H5A 0.2019 0.4464 0.1259 0.033 Uiso calc R 1 . .
C C6 0.11702(11) 0.41346(11) 0.26561(10) 0.0240(2) Uani d . 1 . .
C C7 0.15765(10) 0.31947(11) 0.49000(10) 0.0190(2) Uani d . 1 . .
H H7A 0.0905 0.3931 0.4805 0.023 Uiso calc R 1 . .
C C8 0.08854(9) 0.18701(11) 0.49330(10) 0.0188(2) Uani d . 1 . .
C C9 0.17118(10) 0.21274(12) 0.73885(10) 0.0234(2) Uani d . 1 . .
C C10 0.24295(11) 0.34041(11) 0.73556(10) 0.0249(2) Uani d . 1 . .
H H10A 0.3260 0.3520 0.8228 0.030 Uiso calc R 1 . .
H H10B 0.1799 0.4172 0.7239 0.030 Uiso calc R 1 . .
C C11 0.28713(10) 0.34228(11) 0.62276(10) 0.0220(2) Uani d . 1 . .
H H11A 0.3561 0.2704 0.6369 0.026 Uiso calc R 1 . .
H H11B 0.3300 0.4300 0.6209 0.026 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_
_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
C1 N1 C6 . . 113.25(9) ?
C1 N1 C7 . . 122.88(8) ?
C6 N1 C7 . . 123.25(9) ?
C8 N2 C9 . . 127.22(9) ?
C8 N2 H2B . . 116.4 ?
C9 N2 H2B . . 116.4 ?
O1 C1 N1 . . 123.21(9) ?
O1 C1 C2 . . 129.16(10) ?
N1 C1 C2 . . 107.57(9) ?
C1 C2 C5 . . 105.78(9) ?
C1 C2 C3 . . 112.87(9) ?
C5 C2 C3 . . 89.18(8) ?
C1 C2 H2A . . 115.3 ?
C5 C2 H2A . . 115.3 ?
C3 C2 H2A . . 115.3 ?
C4 C3 C2 . . 89.61(9) ?
C4 C3 H3A . . 113.7 ?
C2 C3 H3A . . 113.7 ?
C4 C3 H3B . . 113.7 ?
C2 C3 H3B . . 113.7 ?
H3A C3 H3B . . 111.0 ?
C3 C4 C5 . . 89.58(8) ?
C3 C4 H4A . . 113.7 ?
C5 C4 H4A . . 113.7 ?
C3 C4 H4B . . 113.7 ?
C5 C4 H4B . . 113.7 ?
H4A C4 H4B . . 111.0 ?
C6 C5 C2 . . 104.34(9) ?
C6 C5 C4 . . 112.24(10) ?
C2 C5 C4 . . 90.21(9) ?
C6 C5 H5A . . 115.6 ?
C2 C5 H5A . . 115.6 ?
C4 C5 H5A . . 115.6 ?
O2 C6 N1 . . 123.98(10) ?
O2 C6 C5 . . 127.86(10) ?
N1 C6 C5 . . 108.14(9) ?
N1 C7 C8 . . 108.95(8) ?
N1 C7 C11 . . 114.71(8) ?
C8 C7 C11 . . 110.57(8) ?
N1 C7 H7A . . 107.4 ?
C8 C7 H7A . . 107.4 ?
C11 C7 H7A . . 107.4 ?
O3 C8 N2 . . 120.82(10) ?
O3 C8 C7 . . 122.84(9) ?
N2 C8 C7 . . 116.33(9) ?
O4 C9 N2 . . 119.20(10) ?
O4 C9 C10 . . 124.80(10) ?
N2 C9 C10 . . 116.00(9) ?
C9 C10 C11 . . 112.47(9) ?
C9 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
C9 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
C10 C11 C7 . . 107.91(9) ?
C10 C11 H11A . . 110.1 ?
C7 C11 H11A . . 110.1 ?
C10 C11 H11B . . 110.1 ?
C7 C11 H11B . . 110.1 ?
H11A C11 H11B . . 108.4 ?
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 . 1.2136(13) ?
O2 C6 . 1.2080(13) ?
O3 C8 . 1.2253(12) ?
O4 C9 . 1.2125(13) ?
N1 C1 . 1.3936(14) ?
N1 C6 . 1.3959(13) ?
N1 C7 . 1.4523(13) ?
N2 C8 . 1.3679(13) ?
N2 C9 . 1.3933(13) ?
N2 H2B . 0.8800 ?
C1 C2 . 1.4984(15) ?
C2 C5 . 1.5364(17) ?
C2 C3 . 1.5654(15) ?
C2 H2A . 1.0000 ?
C3 C4 . 1.5390(18) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.5520(16) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5069(16) ?
C5 H5A . 1.0000 ?
C7 C8 . 1.5191(15) ?
C7 C11 . 1.5298(13) ?
C7 H7A . 1.0000 ?
C9 C10 . 1.4929(16) ?
C10 C11 . 1.5195(15) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 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
N2 H2B O3 3_556 0.88 2.06 2.9426(12) 174.9
C5 H5A O4 2_556 1.00 2.52 3.4424(15) 152.6
C10 H10B O2 3_566 0.99 2.56 3.4228(14) 145.8
C11 H11B O3 2_556 0.99 2.53 3.5026(13) 166.8
C11 H11B O1 2_556 0.99 2.53 3.1072(14) 116.6
C3 H3A O4 1_554 0.99 2.52 3.2577(15) 130.9
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
C6 N1 C1 O1 . . . . 178.13(10) ?
C7 N1 C1 O1 . . . . -10.65(15) ?
C6 N1 C1 C2 . . . . -4.49(11) ?
C7 N1 C1 C2 . . . . 166.72(9) ?
O1 C1 C2 C5 . . . . -174.12(11) ?
N1 C1 C2 C5 . . . . 8.72(11) ?
O1 C1 C2 C3 . . . . 89.96(14) ?
N1 C1 C2 C3 . . . . -87.20(11) ?
C1 C2 C3 C4 . . . . 115.83(10) ?
C5 C2 C3 C4 . . . . 9.02(9) ?
C2 C3 C4 C5 . . . . -8.93(9) ?
C1 C2 C5 C6 . . . . -9.47(11) ?
C3 C2 C5 C6 . . . . 104.11(9) ?
C1 C2 C5 C4 . . . . -122.52(9) ?
C3 C2 C5 C4 . . . . -8.94(9) ?
C3 C4 C5 C6 . . . . -96.51(11) ?
C3 C4 C5 C2 . . . . 9.10(9) ?
C1 N1 C6 O2 . . . . 177.01(10) ?
C7 N1 C6 O2 . . . . 5.83(16) ?
C1 N1 C6 C5 . . . . -1.83(11) ?
C7 N1 C6 C5 . . . . -173.01(9) ?
C2 C5 C6 O2 . . . . -171.68(11) ?
C4 C5 C6 O2 . . . . -75.45(15) ?
C2 C5 C6 N1 . . . . 7.10(11) ?
C4 C5 C6 N1 . . . . 103.32(11) ?
C1 N1 C7 C8 . . . . -55.34(12) ?
C6 N1 C7 C8 . . . . 115.01(10) ?
C1 N1 C7 C11 . . . . 69.19(12) ?
C6 N1 C7 C11 . . . . -120.47(10) ?
C9 N2 C8 O3 . . . . -175.72(9) ?
C9 N2 C8 C7 . . . . 3.25(15) ?
N1 C7 C8 O3 . . . . -24.63(13) ?
C11 C7 C8 O3 . . . . -151.56(9) ?
N1 C7 C8 N2 . . . . 156.42(9) ?
C11 C7 C8 N2 . . . . 29.49(12) ?
C8 N2 C9 O4 . . . . 174.97(10) ?
C8 N2 C9 C10 . . . . -5.28(15) ?
O4 C9 C10 C11 . . . . 153.52(11) ?
N2 C9 C10 C11 . . . . -26.21(13) ?
C9 C10 C11 C7 . . . . 56.95(12) ?
N1 C7 C11 C10 . . . . 178.27(9) ?
C8 C7 C11 C10 . . . . -58.05(11) ?
