Intramolecular cyclization of in situ generated adducts formed between thioamide dianions and thioformamides leading to generation of 5-amino-2-thiazolines and 5-aminothiazoles, and their fluorescence properties.
Murai, Toshiaki; Hori, Fumihiko; Maruyama, Toshifumi; Organic letters 13 (2011) 1718–1721; doi:10.1021/ol200231z

data_1502065
_publ_section_title
;
 Intramolecular cyclization of in situ generated adducts formed between
 thioamide dianions and thioformamides leading to generation of
 5-amino-2-thiazolines and 5-aminothiazoles, and their fluorescence
 properties.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1718
_journal_page_last               1721
_journal_paper_doi               10.1021/ol200231z
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C27 H20 N2 S'
_chemical_formula_sum            'C27 H20 N2 S'
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_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   7.35830(10)
_cell_length_b                   20.2268(4)
_cell_length_c                   28.3714(5)
_cell_measurement_reflns_used    33759
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      3.02
_cell_volume                     4222.65(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
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_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1696.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
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_refine_diff_density_max         0.260
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4836
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_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0432P)^2^+1.4557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1330
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