Multicomponent access to indolo[3,3a-c]isoquinolin-3,6-diones: formal synthesis of (±)-plicamine.
Mijangos, Marco V.; Miranda, Luis D.; Organic & biomolecular chemistry 14 (2016) 3677–3680; doi:10.1039/c6ob00231e

data_7155027
_publ_section_title
;
 Multicomponent access to indolo[3,3a-c]isoquinolin-3,6-diones: formal
 synthesis of (+-)-plicamine.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3677
_journal_page_last               3680
_journal_paper_doi               10.1039/c6ob00231e
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        Synthetic
_chemical_formula_moiety         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.41
_chemical_melting_point          423
_chemical_name_common            'Formil isoplicamine'
_chemical_name_systematic        'Formil isoplicamine'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-16 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                94.7910(10)
_cell_angle_beta                 103.0250(10)
_cell_angle_gamma                108.5480(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4009(4)
_cell_length_b                   10.4848(4)
_cell_length_c                   11.8979(5)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      2.50
_cell_volume                     954.23(7)
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'omega 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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8877
_diffrn_reflns_theta_full        25.29
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0538P)^2^+0.0103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                2480
_reflns_number_total             3449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00231e2.cif
_cod_data_source_block           087mgl13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155027.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7155027
_solved_by                       'Simon Hernandez-Ortega'