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_1555793
_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         C30H22Br2N2O4S2
_chemical_formula_sum            'C30 H22 Br2 N2 O4 S2'
_chemical_formula_weight         698.43
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                80.790(8)
_cell_angle_beta                 71.850(8)
_cell_angle_gamma                65.087(7)
_cell_formula_units_Z            1
_cell_length_a                   7.9207(11)
_cell_length_b                   9.0758(12)
_cell_length_c                   11.1924(15)
_cell_measurement_reflns_used    20099
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.461
_cell_measurement_theta_min      1.916
_cell_volume                     693.02(17)
_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      170(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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  0.0584
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20099
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.461
_diffrn_reflns_theta_min         1.916
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.116
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_description       needle
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6809
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0355P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4438
_reflns_number_total             6809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02499_si_003.cif
_cod_data_source_block           SBR-2185
_cod_database_code               1555793
_shelx_estimated_absorpt_t_min   0.455
_shelx_estimated_absorpt_t_max   0.746
_shelxl_version_number           2013-4
_shelx_res_checksum              10095
_shelx_hkl_checksum              66218