Construction of tetrahydro-β-carboline skeletons via Brønsted acid activation of imide carbonyl group: syntheses of indole alkaloids (±)-harmicine and (±)-10-desbromoarborescidine-A
Mangalaraj, Selvaraj; Ramanathan, Chinnasamy Ramaraj; RSC Advances 2 (2012) 12665–; doi:10.1039/c2ra21734a

data_7238740
_publ_section_title
;
 Construction of tetrahydro-\b-carboline skeletons via Br\/onsted acid
 activation of imide carbonyl group: syntheses of indole alkaloids
 (+-)-harmicine and (+-)-10-desbromoarborescidine-A
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              12665
_journal_paper_doi               10.1039/c2ra21734a
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_chemical_melting_point          436
_chemical_name_common
13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
_chemical_name_systematic
;
13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                99.173(2)
_cell_angle_beta                 106.817(2)
_cell_angle_gamma                101.998(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6018(13)
_cell_length_b                   9.8711(16)
_cell_length_c                   10.1290(17)
_cell_measurement_temperature    298(2)
_cell_volume                     691.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5255
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.060(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0525P)^2^+0.1723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2352
_reflns_number_total             2631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21734a.txt
_cod_data_source_block           crr319
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238740