Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine.
Selvakumar, Jayaraman; Ramanathan, Chinnasamy Ramaraj; Organic & biomolecular chemistry 9 (2011) 7643–7646; doi:10.1039/c1ob06349a

data_7152066
_publ_section_title
;
 Br\/onsted acid assisted activation of imide carbonyl group:
 regioselective synthesis of isoindoloisoquinolinone alkaloid
 (+-)-nuevamine.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7643
_journal_page_last               7646
_journal_paper_doi               10.1039/c1ob06349a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C18 H17 N1 O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.33
_chemical_melting_point          438
_chemical_name_common
;
12b-Hydroxy-1,4-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
;
_chemical_name_systematic
;
12b-Hydroxy-1,4-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_space_group_name_H-M   'P n 21 a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3081(6)
_cell_length_b                   6.5772(4)
_cell_length_c                   20.0573(13)
_cell_measurement_reflns_used    1321
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.0008
_cell_measurement_theta_min      2.7092
_cell_volume                     1491.77(15)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3893
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysalisPro
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.091
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2189
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.792
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0272P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                1271
_reflns_number_total             2189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06349a.txt
_cod_data_source_block           crr45
_cod_original_sg_symbol_H-M      'p n 21 a'
_cod_original_formula_sum        'C18 H17 N1 O4'
_cod_database_code               7152066