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_4032894
_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            'C12 H9 N O2 S'
_chemical_formula_weight         231.26
_chemical_name_common            JBK-477
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 105.4655(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2740(4)
_cell_length_b                   11.8466(4)
_cell_length_c                   7.7264(2)
_cell_measurement_reflns_used    9086
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.1334
_cell_measurement_theta_min      2.4329
_cell_volume                     1082.78(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21368
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0690
_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^)+(0.1000P)^2^+1.1411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                1660
_reflns_number_total             1905
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02077_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4032893--4032894.cif.'
_cod_database_code               4032894