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_7152064
_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         'C16 H12 Br1 N1 O2'
_chemical_formula_sum            'C16 H12 Br N O2'
_chemical_formula_weight         330.17
_chemical_melting_point          436
_chemical_name_common
;
12b-Hydroxy-3-bromo-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
;
_chemical_name_systematic
;
12b-Hydroxy-3-bromo-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2011-05-12
_audit_creation_method
;
Olex2 1.1
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 134.52(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   23.930(3)
_cell_length_b                   9.1192(4)
_cell_length_c                   17.171(2)
_cell_measurement_reflns_used    2978
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1543
_cell_measurement_theta_min      3.3215
_cell_volume                     2671.7(10)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_solution    'smtbx-flip (Bourhis, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989796
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7366
_diffrn_reflns_theta_full        24.9999634556
_diffrn_reflns_theta_max         29.1543
_diffrn_reflns_theta_min         3.3215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysAlisPro
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method 'Ethylacetate, Hexane'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.477479
_refine_diff_density_min         -0.657691
_refine_diff_density_rms         0.097830
_refine_ls_d_res_high            0.840866
_refine_ls_d_res_low             6.121043
_refine_ls_goodness_of_fit_ref   1.025330
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025330
_refine_ls_R_factor_all          0.053107
_refine_ls_R_factor_gt           0.039394
_refine_ls_shift/su_max          0.0039
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+3.9665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.065956
_reflns_number_gt                1868
_reflns_number_total             2328
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            c1ob06349a.txt
_cod_data_source_block           CRR-63-CRR-228
_cod_original_cell_volume        2671.5(13)
_cod_original_formula_sum        'C16 H12 Br1 N1 O2'
_cod_database_code               7152064