Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of Benzothiazoles to 1-Amino-<i>N</i>-(2-(phenylthio)phenyl)methanimine.
Zheng, Nian; Liu, Ce; Ding, Ya-Nan; Shi, Wei-Yu; Zhang, Bo-Sheng; Liang, Yong-Min; The Journal of organic chemistry 85 (2020) 7666–7673; doi:10.1021/acs.joc.9b03489

data_4038476
_publ_section_title
;
 Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of
 Benzothiazoles to 1-Amino-<i>N</i>-(2-(phenylthio)phenyl)methanimine.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7666
_journal_page_last               7673
_journal_paper_doi               10.1021/acs.joc.9b03489
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 Cl N2 O S'
_chemical_formula_sum            'C17 H17 Cl N2 O S'
_chemical_formula_weight         332.83
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.731(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4728(4)
_cell_length_b                   9.39367(19)
_cell_length_c                   22.5176(5)
_cell_measurement_reflns_used    4271
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      69.7230
_cell_measurement_theta_min      7.2670
_cell_volume                     3336.87(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 48

  2 omega  -18.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -60.0000 37

  3 omega  -61.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -60.0000 33

  4 omega   21.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000   59.4147 26

  5 omega   55.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 67

  6 omega   30.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 97

  7 omega  104.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 44

  8 omega   35.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 56

  9 omega  101.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  120.0000 63

 10 omega   40.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 75

 11 omega   67.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 78

 12 omega   38.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 49

 13 omega   49.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 39

 14 omega  146.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 28

 15 omega  107.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 25

 16 omega   34.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 37

 17 omega  107.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 68

 18 omega  127.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0366115000
_diffrn_orient_matrix_UB_12      -0.0746702000
_diffrn_orient_matrix_UB_13      -0.0629712000
_diffrn_orient_matrix_UB_21      -0.0739680000
_diffrn_orient_matrix_UB_22      -0.0576768000
_diffrn_orient_matrix_UB_23      0.0220779000
_diffrn_orient_matrix_UB_31      -0.0521491000
_diffrn_orient_matrix_UB_32      0.1341342000
_diffrn_orient_matrix_UB_33      -0.0255438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12001
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         4.100
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.8050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4821
_reflns_number_total             5806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03489_si_002.cif
_cod_data_source_block           zhengn1_0705
_cod_depositor_comments
'Adding full bibliography for 4038476--4038478.cif.'
_cod_original_cell_volume        3336.86(14)
_cod_database_code               4038476
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28),
  C30(H30)
;
_shelx_res_checksum              15533
_shelx_hkl_checksum              3082
_olex2_date_sample_data_collection 2019-07-05
_olex2_submission_special_instructions 'No special instructions were received'