Smiles rearrangement as a tool for the preparation of dihydrodipyridopyrazines.
Patriciu, Oana-Irina; Fînaru, Adriana-Luminita; Massip, Stéphane; Leger, Jean-Michel; Jarry, Christian; Guillaumet, Gérald; Organic letters 11 (2009) 5502–5505; doi:10.1021/ol902369v

data_1504301
_publ_section_title
;
 Smiles rearrangement as a tool for the preparation of
 dihydrodipyridopyrazines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5502
_journal_page_last               5505
_journal_paper_doi               10.1021/ol902369v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C16 H19 Br N4 O'
_chemical_formula_weight         363.26
_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                98.908(10)
_cell_angle_beta                 102.359(10)
_cell_angle_gamma                109.915(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5380(10)
_cell_length_b                   10.542(2)
_cell_length_c                   12.0440(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      25.0
_cell_volume                     851.5(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf Nonius cad-4 diffractometer'
_diffrn_measurement_method       \W-2\Scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0101
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2893
_diffrn_reflns_theta_full        64.92
_diffrn_reflns_theta_max         64.92
_diffrn_reflns_theta_min         3.88
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.346
_exptl_absorpt_correction_T_max  0.7098
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.076(3)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0679P)^2^+0.3347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2755
_reflns_number_total             2893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902369v_si_003.cif
_cod_data_source_block           po355
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504301