Temperature-Controlled Synthesis of Substituted Pyridine Derivatives via the [5C + 1N] Annulation of 1,1-Bisalkylthio-1,4-pentanedienes and Ammonium Acetate
Hu, Jianglei; Zhang, Qian; Yuan, Hongjuan; Liu, Qun; The Journal of Organic Chemistry 73 (2008) 8132–; doi:10.1021/jo802007a

data_4028925
_publ_section_title
;
 Temperature-Controlled Synthesis of Substituted Pyridine Derivatives via
 the [5C + 1N] Annulation of 1,1-Bisalkylthio-1,4-pentanedienes and
 Ammonium Acetate
;
_journal_issue                   20
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              8132
_journal_paper_doi               10.1021/jo802007a
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C16 H17 N3 O S'
_chemical_formula_weight         299.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.73(3)
_cell_angle_beta                 80.57(3)
_cell_angle_gamma                77.57(3)
_cell_formula_units_Z            4
_cell_length_a                   10.597(2)
_cell_length_b                   12.793(3)
_cell_length_c                   13.519(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1600.0(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 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8811
_diffrn_reflns_theta_full        25.87
_diffrn_reflns_theta_max         25.87
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.204
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6006
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                2709
_reflns_number_total             6006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802007asup1.cif
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_cod_original_cell_volume        1600.0(6)
_cod_database_code               4028925
_cod_duplicate_entry 4023782