Unprecedented Rearrangement of 2-(2-Aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides to 2,3-Dihydro-1H-imidazo[1,2-b]indazoles
Jan Kočí; Allen G. Oliver; Viktor Krchňák; Journal of Organic Chemistry 75 (2010) 502–505; doi:10.1021/jo902301x

data_4025170
_publ_contact_author_address
;
Department of Chemistry and Biochemistry,
University of Notre Dame,
Notre Dame, IN 46556
USA
;
_publ_contact_author_email       viktor.krchnak.1@nd.edu
_publ_contact_author_fax         '+1 574 631 6652'
_publ_contact_author_name        'Viktor Krchnak'
_publ_contact_author_phone       '+1 574 631 5113'
_publ_section_title
;
 Unprecedented Rearrangement of
 2-(2-Aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides
 to 2,3-Dihydro-1H-imidazo[1,2-b]indazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              502
_journal_page_last               505
_journal_paper_doi               10.1021/jo902301x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C19 H20 N4 O'
_chemical_formula_sum            'C19 H20 N4 O'
_chemical_formula_weight         320.39
_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
_cell_angle_alpha                93.389(3)
_cell_angle_beta                 95.731(3)
_cell_angle_gamma                104.216(3)
_cell_formula_units_Z            4
_cell_length_a                   7.6124(4)
_cell_length_b                   12.5446(7)
_cell_length_c                   17.6687(9)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.65
_cell_volume                     1621.29(15)
_computing_cell_refinement       'Bruker SAINT v7.53A'
_computing_data_collection       'Bruker APEX-II v2008-6'
_computing_data_reduction        'Bruker SAINT v7.53A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.607
_diffrn_measured_fraction_theta_max 0.607
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13582
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.9421
_exptl_absorpt_correction_T_min  0.8611
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.5481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                2981
_reflns_number_total             3623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902301x_si_001.cif
_cod_data_source_block           koci1
_cod_database_code               4025170