Unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines. the first synthesis of 1,4,6,10-tetraazaadamantanes.
Semakin, Artem N.; Sukhorukov, Alexey Yu; Lesiv, Alexey V.; Ioffe, Sema L.; Lyssenko, Konstantin A.; Nelyubina, Yulia V.; Tartakovsky, Vladimir A.; Organic letters 11 (2009) 4072–4075; doi:10.1021/ol9015157

data_1504109
_publ_section_title
;
 Unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines. the
 first synthesis of 1,4,6,10-tetraazaadamantanes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4072
_journal_page_last               4075
_journal_paper_doi               10.1021/ol9015157
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C18 H2 Br N4 O2'
_chemical_formula_weight         386.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 91.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8160(16)
_cell_length_b                   19.390(4)
_cell_length_c                   12.728(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1928.3(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0363
_diffrn_reflns_av_sigmaI/netI    0.1126
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4055
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    2.684
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             945
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0244P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2287
_reflns_number_total             3777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9015157_si_002.cif
_cod_data_source_block           a
_cod_database_code               1504109