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_4022347
_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         'C22 H29 N3 O1 S1'
_chemical_formula_sum            'C22 H29 N3 O S'
_chemical_formula_weight         383.54
_chemical_name_systematic
;
S-(3-cyclohexenyl)-2-phenylthiocarbamoyl-2-methyl-trans-perhydroquinoxalin-3-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2002-07-02T12:19:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                71.2330(10)
_cell_angle_beta                 75.7190(10)
_cell_angle_gamma                68.7990(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4700(2)
_cell_length_b                   9.7190(2)
_cell_length_c                   12.9690(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.98
_cell_measurement_theta_min      3.07
_cell_volume                     1042.15(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10828
_diffrn_reflns_theta_full        31.98
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         7165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.1848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                5144
_reflns_number_total             7165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026756tsi20030103_070058_2.cif
_cod_data_source_block           9a
_cod_database_code               4022347