Synthesis of Bicyclic Isothiazoles through an Intramolecular Rhodium-Catalyzed Transannulation of Cyanothiadiazoles.
Seo, Boram; Kim, Hyunseok; Kim, Ya Gob; Baek, Yonghyeon; Um, Kyusik; Lee, Phil Ho; The Journal of organic chemistry 82 (2017) 10574–10582; doi:10.1021/acs.joc.7b02077

data_4032893
_publ_section_title
;
 Synthesis of Bicyclic Isothiazoles through an Intramolecular
 Rhodium-Catalyzed Transannulation of Cyanothiadiazoles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10574
_journal_page_last               10582
_journal_paper_doi               10.1021/acs.joc.7b02077
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C16 H15 N O2 S'
_chemical_formula_weight         285.35
_chemical_name_common            ye617
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                103.1892(14)
_cell_angle_beta                 97.2730(16)
_cell_angle_gamma                90.9588(16)
_cell_formula_units_Z            2
_cell_length_a                   7.0936(3)
_cell_length_b                   9.3673(4)
_cell_length_c                   10.8449(4)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.6336
_cell_measurement_theta_min      2.6013
_cell_volume                     695.19(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13752
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1431P)^2^+0.3543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2082
_refine_ls_wR_factor_ref         0.2182
_reflns_number_gt                2216
_reflns_number_total             2525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02077_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4032893--4032894.cif.'
_cod_database_code               4032893