Synthesis of 1,4-Diazines by Ring Expansion of 1,3-Diazines
Barbara Zaleska; Robert Socha; Marcin Karelus; Edward Szneler; Jacek Grochowski; Paweł Serda; Journal of Organic Chemistry 68 (2003) 2334–2337; doi:10.1021/jo026756t

data_4022346
_publ_section_title
;
 Synthesis of 1,4-Diazines by Ring Expansion of 1,3-Diazines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2334
_journal_page_last               2337
_journal_paper_doi               10.1021/jo026756t
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H19 N3 O1 S1'
_chemical_formula_sum            'C14 H19 N3 O S'
_chemical_formula_weight         277.38
_chemical_melting_point          187.0
_chemical_name_systematic
;
1-N-ethyl-2-phenylthiocarbamoyl-2-methyl-piperazin-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 96.1180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8549(2)
_cell_length_b                   6.31970(10)
_cell_length_c                   16.6171(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1446.69(5)
_computing_data_reduction        DENZO
_computing_molecular_graphics    'Ortep-3 for Windows'
_computing_publication_material  'WINGX (Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  '\k-geometry diffractometer'
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11888
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9369
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       yellow
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.057(6)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.2597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                3359
_reflns_number_total             4205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026756tsi20030103_070058_1.cif
_cod_data_source_block           5b
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4022346