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_1504300
_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            'C10 H9 Br N4'
_chemical_formula_weight         265.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.20(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6380(10)
_cell_length_b                   6.3800(10)
_cell_length_c                   18.833(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      25.0
_cell_volume                     1035.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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    0.0090
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1716
_diffrn_reflns_theta_full        64.89
_diffrn_reflns_theta_max         64.89
_diffrn_reflns_theta_min         4.71
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    5.177
_exptl_absorpt_correction_T_max  0.6255
_exptl_absorpt_correction_T_min  0.4913
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.029(2)
_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   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1217P)^2^+1.5543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                1663
_reflns_number_total             1716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902369v_si_002.cif
_cod_data_source_block           po184
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1504300