Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Nitriles.
Seo, Boram; Kim, Ya Gob; Lee, Phil Ho; Organic letters 18 (2016) 5050–5053; doi:10.1021/acs.orglett.6b02499

data_1555792
_publ_section_title
;
 Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of
 1,2,3-Thiadiazoles with Nitriles.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5050
_journal_page_last               5053
_journal_paper_doi               10.1021/acs.orglett.6b02499
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         C30H24N2O4S2
_chemical_formula_sum            'C30 H24 N2 O4 S2'
_chemical_formula_weight         540.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.7628(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4528(3)
_cell_length_b                   14.3902(4)
_cell_length_c                   8.7251(3)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.2556
_cell_measurement_theta_min      2.4101
_cell_volume                     1310.89(7)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       'not measured'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25532
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         1.951
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0913
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1791P)^2^+1.3952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2390
_refine_ls_wR_factor_ref         0.2587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1914
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02499_si_002.cif
_cod_data_source_block           SBR-2182
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555792
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              14272
_shelx_hkl_checksum              38703