Synthesis of Zwitterionic Compounds: Fully Saturated Pyrimidinylium and 1,3-Diazepinylium Derivatives via the Novel Rearrangement of 3-Oxobutanoic Acid Thioanilide Derivatives
Barbara Zaleska; Tomasz Bazanek; Robert Socha; Marcin Karelus; Jacek Grochowski; Paweł Serda; Journal of Organic Chemistry 67 (2002) 4526–4529; doi:10.1021/jo025602a

data_4022224
_publ_contact_author_address
;
Department of Organic Chemistry
Jagiellonian University
Ingardena 3
30-060 Krakow
Poland
;
_publ_contact_author_email       zaleska@chemia.uj.edu.pl
_publ_contact_author_fax         '48 12 6340515'
_publ_contact_author_name        'Zaleska, Barbara'
_publ_contact_author_phone       '48 12 6336377'
_publ_section_title
;
 Synthesis of Zwitterionic Compounds: Fully Saturated Pyrimidinylium
 and 1,3-Diazepinylium Derivatives via the Novel Rearrangement
 of 3-Oxobutanoic Acid Thioanilide Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4526
_journal_page_last               4529
_journal_paper_doi               10.1021/jo025602a
_journal_volume                  67
_journal_year                    2002
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H17 N3 O1 S1'
_chemical_formula_structural     'C13 H17 N3 O S'
_chemical_formula_sum            'C13 H17 N3 O S'
_chemical_formula_weight         263.36
_chemical_name_systematic
;
((+/-) 2-[2'-(1',3',4',5',6'-Pentahydropyrimidine)] lactic acid
thioanilide zwitterionic
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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             2001-08-14T17:29:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.0000(10)
_cell_angle_beta                 90.0000(10)
_cell_angle_gamma                120.0000
_cell_formula_units_Z            18
_cell_length_a                   27.4345(2)
_cell_length_b                   27.4345(4)
_cell_length_c                   9.47000(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.7107
_cell_volume                     6172.69(12)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23223
_diffrn_reflns_theta_full        30.1
_diffrn_reflns_theta_max         30.1
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0595P)^2^+3.4971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2826
_reflns_number_total             4017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo025602a_s1.cif
_cod_data_source_block           pp3
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4022224