Synthesis of 6-amino-3,4-dihydroisoquinolinium derivatives by ring-opening reactions of acridizinium ions.
Deiseroth, Hans-Jörg; Granzhan, Anton; Ihmels, Heiko; Schlosser, Marc; Tian, Maoqun; Organic letters 10 (2008) 757–760; doi:10.1021/ol702792r

data_1504508
_publ_section_title
;
 Synthesis of 6-amino-3,4-dihydroisoquinolinium derivatives by
 ring-opening reactions of acridizinium ions.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              757
_journal_page_last               760
_journal_paper_doi               10.1021/ol702792r
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C34 H38 Cl F N4 O4'
_chemical_formula_weight         621.13
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.433(3)
_cell_length_b                   18.544(4)
_cell_length_c                   14.831(3)
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.7
_cell_volume                     3176.6(14)
_computing_cell_refinement       'STOE-IPDS (STOE & Cie, 1999)'
_computing_data_collection       'STOE-IPDS (STOE & Cie, 1999)'
_computing_data_reduction        'STOE-IPDS (STOE & Cie, 1999)'
_computing_molecular_graphics    'DIAMOND 3.1e (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.864
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       \j-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  0.0696
_diffrn_reflns_av_sigmaI/netI    0.1517
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12849
_diffrn_reflns_theta_full        29.33
_diffrn_reflns_theta_max         29.33
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.284
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0010(8)
_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   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         7533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.1711
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1055P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.2048
_reflns_number_gt                3067
_reflns_number_total             7533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702792r-file001.cif
_cod_data_source_block           Ihmels
_cod_original_cell_volume        3176.6(11)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1504508