#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/51/2015149.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_2015149
loop_
_publ_author_name
'Tripathi, Anil Kumar'
'Bruhn, Clemens'
'Flock, Susanne'
'Frauenrath, Herbert'
_publ_section_title
;
 The endo and exo isomers of
 1-(4-isopropyl-3,5-dioxa-8-azabicyclo[5.1.0]octan-8-yl)pyrrolidine-2,5-dione
;
_journal_coeditor_code           GD1417
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o705
_journal_page_last               o706
_journal_paper_doi               10.1107/S0108270105035134
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C12 H18 N2 O4'
_chemical_formula_sum            'C12 H18 N2 O4'
_chemical_formula_weight         254.28
_chemical_name_systematic
;
endo-
1-(4-isopropyl-3,5-dioxa-8-azabicyclo[5.1.0]octan-8-yl)pyrrolidine-2,5-dione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.250(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1449(11)
_cell_length_b                   7.8343(10)
_cell_length_c                   13.080(3)
_cell_measurement_reflns_used    7302
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      1.58
_cell_volume                     619.6(2)
_computing_cell_refinement       'Please provide missing details'
_computing_data_collection       'Please provide missing details'
_computing_data_reduction        'Please provide missing details'
_computing_molecular_graphics    'Please provide missing details'
_computing_publication_material  'Please provide missing details'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8393
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9535
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED32 (Stoe & Cie, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1244
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.044P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                998
_reflns_number_total             1244
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1417.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2015149
_cod_database_fobs_code          2015149
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 0.1562(5) 0.8397(4) 0.6551(2) 0.0359(7) Uani d . 1 . . C
H1A 0.2998 0.8933 0.6500 0.043 Uiso calc R 1 . . H
H1B 0.1719 0.7149 0.6472 0.043 Uiso calc R 1 . . H
C2 0.1003(5) 0.8771(4) 0.7606(2) 0.0310(6) Uani d . 1 . . C
H2A 0.1520 0.9890 0.7930 0.037 Uiso calc R 1 . . H
C3 -0.1000(4) 0.8033(4) 0.7901(2) 0.0314(6) Uani d . 1 . . C
H3A -0.1692 0.8701 0.8411 0.038 Uiso calc R 1 . . H
C4 -0.2544(5) 0.6976(4) 0.7130(2) 0.0345(7) Uani d . 1 . . C
H4B -0.1758 0.5945 0.6951 0.041 Uiso calc R 1 . . H
H4A -0.3809 0.6599 0.7448 0.041 Uiso calc R 1 . . H
C5 -0.1931(4) 0.7912(4) 0.5452(2) 0.0314(6) Uani d . 1 . . C
H5A -0.1396 0.6725 0.5364 0.038 Uiso calc R 1 . . H
C6 -0.3220(5) 0.8561(4) 0.4427(2) 0.0341(6) Uani d . 1 . . C
H6A -0.3517 0.9805 0.4504 0.041 Uiso calc R 1 . . H
C7 -0.1823(5) 0.8357(4) 0.3577(2) 0.0403(7) Uani d . 1 . . C
H7A -0.1594 0.7141 0.3457 0.048 Uiso calc R 1 . . H
H7B -0.0389 0.8916 0.3796 0.048 Uiso calc R 1 . . H
H7C -0.2592 0.8885 0.2933 0.048 Uiso calc R 1 . . H
C8 -0.5429(5) 0.7652(4) 0.4124(2) 0.0421(8) Uani d . 1 . . C
H8C -0.6164 0.8051 0.3439 0.051 Uiso calc R 1 . . H
H8B -0.6364 0.7902 0.4639 0.051 Uiso calc R 1 . . H
H8A -0.5180 0.6418 0.4100 0.051 Uiso calc R 1 . . H
C9 0.3970(5) 0.8568(4) 0.9687(2) 0.0357(7) Uani d . 1 . . C
C10 0.4386(5) 0.8615(4) 1.0854(2) 0.0403(7) Uani d . 1 . . C
H10A 0.4573 0.9805 1.1109 0.048 Uiso calc R 1 . . H
H10B 0.5731 0.7958 1.1143 0.048 Uiso calc R 1 . . H
C11 0.2335(5) 0.7804(4) 1.1162(2) 0.0398(7) Uani d . 1 . . C
H11B 0.2757 0.6853 1.1656 0.048 Uiso calc R 1 . . H
H11A 0.1492 0.8658 1.1490 0.048 Uiso calc R 1 . . H
C12 0.0983(5) 0.7156(4) 1.0165(2) 0.0354(7) Uani d . 1 . . C
N1 0.1217(4) 0.7252(3) 0.83085(17) 0.0313(5) Uani d . 1 . . N
N2 0.2005(4) 0.7706(3) 0.93619(15) 0.0299(5) Uani d . 1 . . N
O1 0.5120(3) 0.9170(3) 0.91070(15) 0.0453(6) Uani d . 1 . . O
O2 -0.0704(4) 0.6317(3) 1.00440(16) 0.0455(6) Uani d . 1 . . O
O3 -0.0102(3) 0.9024(3) 0.57294(13) 0.0347(5) Uani d . 1 . . O
O4 -0.3350(3) 0.7922(3) 0.62015(13) 0.0341(5) Uani d . 1 . . O
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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
_geom_angle_publ_flag
O3 C1 C2 111.8(2) n
O3 C1 H1A 109.3 ?
C2 C1 H1A 109.3 ?
O3 C1 H1B 109.3 ?
C2 C1 H1B 109.3 ?
H1A C1 H1B 107.9 ?
C3 C2 N1 60.83(18) n
C3 C2 C1 120.0(2) n
N1 C2 C1 113.4(2) n
C3 C2 H2A 116.8 ?
N1 C2 H2A 116.8 ?
C1 C2 H2A 116.8 ?
C2 C3 N1 60.33(17) n
C2 C3 C4 119.8(2) n
N1 C3 C4 116.0(2) n
C2 C3 H3A 116.3 ?
N1 C3 H3A 116.3 ?
C4 C3 H3A 116.3 ?
O4 C4 C3 111.4(2) n
O4 C4 H4B 109.3 ?
C3 C4 H4B 109.3 ?
O4 C4 H4A 109.3 ?
C3 C4 H4A 109.3 ?
H4B C4 H4A 108.0 ?
O3 C5 O4 112.1(2) n
O3 C5 C6 106.6(2) n
O4 C5 C6 108.6(2) n
O3 C5 H5A 109.8 ?
O4 C5 H5A 109.8 ?
C6 C5 H5A 109.8 ?
C5 C6 C8 112.0(2) n
C5 C6 C7 109.6(2) n
C8 C6 C7 110.7(2) n
C5 C6 H6A 108.2 ?
C8 C6 H6A 108.2 ?
C7 C6 H6A 108.2 ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C6 C8 H8C 109.5 ?
C6 C8 H8B 109.5 ?
H8C C8 H8B 109.5 ?
C6 C8 H8A 109.5 ?
H8C C8 H8A 109.5 ?
H8B C8 H8A 109.5 ?
O1 C9 N2 124.7(3) n
O1 C9 C10 127.5(3) n
N2 C9 C10 107.8(2) n
C9 C10 C11 104.9(2) n
C9 C10 H10A 110.8 ?
C11 C10 H10A 110.8 ?
C9 C10 H10B 110.8 ?
C11 C10 H10B 110.8 ?
H10A C10 H10B 108.8 ?
C12 C11 C10 105.5(2) n
C12 C11 H11B 110.7 ?
C10 C11 H11B 110.7 ?
C12 C11 H11A 110.7 ?
C10 C11 H11A 110.7 ?
H11B C11 H11A 108.8 ?
O2 C12 N2 124.2(3) n
O2 C12 C11 128.6(3) n
N2 C12 C11 107.3(3) n
N2 N1 C2 112.0(2) n
N2 N1 C3 111.9(2) n
C2 N1 C3 58.84(17) n
C9 N2 C12 114.1(2) n
C9 N2 N1 123.2(2) n
C12 N2 N1 122.3(2) n
C5 O3 C1 114.2(2) n
C5 O4 C4 114.8(2) n
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
C1 O3 . 1.432(3) n
C1 C2 . 1.509(4) n
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.472(4) n
C2 N1 . 1.495(3) n
C2 H2A . 1.0000 ?
C3 N1 . 1.502(4) n
C3 C4 . 1.504(4) n
C3 H3A . 1.0000 ?
C4 O4 . 1.434(3) n
C4 H4B . 0.9900 ?
C4 H4A . 0.9900 ?
C5 O3 . 1.417(3) n
C5 O4 . 1.423(3) n
C5 C6 . 1.519(4) n
C5 H5A . 1.0000 ?
C6 C8 . 1.521(4) n
C6 C7 . 1.529(4) n
C6 H6A . 1.0000 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8C . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8A . 0.9800 ?
C9 O1 . 1.219(3) n
C9 N2 . 1.382(4) n
C9 C10 . 1.503(4) n
C10 C11 . 1.528(4) n
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.504(4) n
C11 H11B . 0.9900 ?
C11 H11A . 0.9900 ?
C12 O2 . 1.213(3) n
C12 N2 . 1.385(4) n
N1 N2 . 1.422(3) n
