Highly diastereoselective synthesis of C6-functionalized dihydroimidazotriazines.
Garnier, Ethel; Guillard, Jérôme; Pasquinet, Eric; Suzenet, Franck; Poullain, Didier; Jarry, Christian; Léger, Jean-Michel; Lebret, Bruno; Guillaumet, Gérald; Organic letters 5 (2003) 4595–4598; doi:10.1021/ol035743e

data_1507398
_publ_section_title
;
 Highly diastereoselective synthesis of C6-functionalized
 dihydroimidazotriazines.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              4595
_journal_page_last               4598
_journal_paper_doi               10.1021/ol035743e
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C7 H9 Br N4 O3'
_chemical_formula_weight         277.09
_space_group_IT_number           86
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.859(2)
_cell_length_b                   21.859(2)
_cell_length_c                   4.2150(10)
_cell_measurement_temperature    296(2)
_cell_volume                     2014.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    0.0236
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1275
_diffrn_reflns_theta_full        54.95
_diffrn_reflns_theta_max         54.95
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    5.577
_exptl_absorpt_correction_T_max  0.6055
_exptl_absorpt_correction_T_min  0.3362
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.00138(12)
_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   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+2.3343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                989
_reflns_number_total             1275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035743esi20030910_051320.cif
_cod_data_source_block           eg092
_cod_database_code               1507398