Synthesis of a family of 3-alkyl- or 3-aryl-substituted 1,2-dihydroquinazolinium salts and their isomerization to 4-iminium-1,2,3,4-tetrahydroquinolines.
Vicente, José; Chicote, María Teresa; Martínez-Martínez, Antonio Jesús; Bautista, Delia; Jones, Peter G.; Organic & biomolecular chemistry 9 (2011) 2279–2285; doi:10.1039/c0ob00982b

data_7151792
_publ_section_title
;
 Synthesis of a family of 3-alkyl- or 3-aryl-substituted
 1,2-dihydroquinazolinium salts and their isomerization to
 4-iminium-1,2,3,4-tetrahydroquinolines.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2279
_journal_page_last               2285
_journal_paper_doi               10.1039/c0ob00982b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C25 H24 Cl3 F3 N2 O3 S'
_chemical_formula_weight         595.87
_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                 94.238(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8646(11)
_cell_length_b                   12.0601(11)
_cell_length_c                   20.4915(18)
_cell_measurement_reflns_used    5996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.50
_cell_volume                     2677.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       \w-scan
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32587
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.73
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_correction_T_min  0.8680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment
'NH free with DFIX, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0447P)^2^+1.9022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                5168
_reflns_number_total             6510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00982b.txt
_cod_data_source_block           ajf49rbs
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               7151792