A comparison of 3,4,6a,7,10,10a-hexahydro-7,10-epoxypyrimido[2,1-<i>a</i>]isoindol-6(2<i>H</i>)-one and 2-(2-aminoethyl)-3a,4,7,7a-tetrahydro-1<i>H</i>-4,7-epoxyisoindole-1,3(2<i>H</i>)-dione: structural and reactivity differences of two homologous tricyclic imides
Mitchell, Lauren A.; Stanley, Julie M.; Espinosa De Hoyos, Liliana; Holliday, Bradley J.; Acta Crystallographica Section C 69 (2013) 638–641; doi:10.1107/S0108270113010706

data_2018990
_publ_section_title
;
 A comparison of
 3,4,6a,7,10,10a-hexahydro-7,10-epoxypyrimido[2,1-<i>a</i>]isoindol-6(2<i>H</i>)-one
 and
 2-(2-aminoethyl)-3a,4,7,7a-tetrahydro-1<i>H</i>-4,7-epoxyisoindole-1,3(2<i>H</i>)-dione:
 structural and reactivity differences of two homologous tricyclic imides
;
_journal_coeditor_code           SF3191
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              638
_journal_page_last               641
_journal_paper_doi               10.1107/S0108270113010706
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H12 N2 O2'
_chemical_formula_moiety         'C11 H12 N2 O2'
_chemical_formula_sum            'C11 H12 N2 O2'
_chemical_formula_weight         204.23
_chemical_name_systematic
3,4,6a,7,10,10a-Fexahydro-7,10-epoxypyrimido[2,1-<i>a</i>]isoindol-6(2<i>H</i>)-one
_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           SHELXL97
_cell_angle_alpha                90.000
_cell_angle_beta                 94.445(7)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   4.916(2)
_cell_length_b                   8.998(3)
_cell_length_c                   21.604(6)
_cell_measurement_reflns_used    21982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.03
_cell_measurement_theta_min      7.26
_cell_volume                     952.8(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SIR97 (Altomare <i>et al.</i>, 1999) within WinGX (Farrugia,
2012)
;
_computing_structure_solution    'SIR97 (Altomare <i>et al.</i>, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Rigaku AFC12 with Saturn 724+ CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21174
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.821722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0372
_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/[\s^2^(Fo^2^)+(0.0501P)^2^+0.4632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2031
_reflns_number_total             2193
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3191.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018990
_cod_database_fobs_code          2018990