Total Synthesis of (±)-Eucophylline. A Free-Radical Approach to the Synthesis of the Azabicyclo[3.3.1]nonane Skeleton.
Hassan, Haitham; Mohammed, Shireen; Robert, Frédéric; Landais, Yannick; Organic letters 17 (2015) 4518–4521; doi:10.1021/acs.orglett.5b02218

data_1534102
_publ_section_title
;
 Total Synthesis of (+-)-Eucophylline. A Free-Radical Approach to the
 Synthesis of the Azabicyclo[3.3.1]nonane Skeleton.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4518
_journal_page_last               4521
_journal_paper_doi               10.1021/acs.orglett.5b02218
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C15 H17 N3'
_chemical_formula_weight         239.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 90.344(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.507(2)
_cell_length_b                   9.4923(13)
_cell_length_c                   14.387(2)
_cell_measurement_reflns_used    1942
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      6.59
_cell_volume                     1298.3(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10621
_diffrn_reflns_theta_full        68.33
_diffrn_reflns_theta_max         68.33
_diffrn_reflns_theta_min         6.59
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  0.9182
_exptl_absorpt_correction_T_min  0.8455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0135(9)
_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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0564P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                1942
_reflns_number_total             2344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02218_si_002.cif
_cod_data_source_block           ms444
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1534102