Iron-Catalyzed Formation of 2-Aminopyridines from Diynes and Cyanamides
Timothy K. Lane; Brendan R. D'Souza; Janis Louie; Journal of Organic Chemistry 77 (2012) 7555–7563; doi:10.1021/jo3012418

data_4027457
_publ_section_title
;
 Iron-Catalyzed Formation of 2-Aminopyridines from Diynes and Cyanamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7555
_journal_page_last               7563
_journal_paper_doi               10.1021/jo3012418
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety
'C25 H27 Br2 Fe N3, C4 H8 O1, (C1.33 H2.67 O0.33)'
_chemical_formula_sum            'C30.33 H37.67 Br2 Fe N3 O1.33'
_chemical_formula_weight         681.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           161
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   24.4458(5)
_cell_length_b                   24.4458(5)
_cell_length_c                   26.3085(4)
_cell_measurement_reflns_used    6326
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     13615.6(4)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'WinGX, Ortep3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       'Phi and Omega scan'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12284
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.6479
_exptl_absorpt_correction_T_min  0.4708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       prism
_exptl_crystal_F_000             6252
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(8)
_refine_ls_extinction_coef       0.00012(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   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6688
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                5369
_reflns_number_total             6688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3012418_si_002.cif
_cod_data_source_block           jl042
_cod_original_cell_volume        13615.5(4)
_cod_original_sg_symbol_Hall     'R 3-2"c'
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               4027457