Acyl-isothiocyanates as efficient thiocyanate transfer reagents.
Palsuledesai, Charuta C.; Murru, Siva; Sahoo, Santosh K.; Patel, Bhisma K.; Organic letters 11 (2009) 3382–3385; doi:10.1021/ol901561j

data_1504116
_publ_section_title
;
 Acyl-isothiocyanates as efficient thiocyanate transfer reagents.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3382
_journal_page_last               3385
_journal_paper_doi               10.1021/ol901561j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C14 H13 N O4 S'
_chemical_formula_sum            'C14 H13 N O4 S'
_chemical_formula_weight         291.31
_chemical_name_systematic
'(2E)-ethyl 2-(benzoylimino)-5-methyl-1,3-oxathiole-4-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.920(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2571(6)
_cell_length_b                   13.4283(7)
_cell_length_c                   11.0755(6)
_cell_measurement_reflns_used    4332
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      34.22
_cell_measurement_theta_min      2.39
_cell_volume                     1371.69(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17769
_diffrn_reflns_theta_full        31.22
_diffrn_reflns_theta_max         31.22
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'SMART APEX 2'
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       reactangular
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'Ethyl acetate hexane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0447
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                3213
_reflns_number_total             4332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901561j_si_002.cif
_cod_data_source_block           2-imino_oxathioline
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1504116