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_4038478
_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         'C21 H24 N2 O2 S'
_chemical_formula_sum            'C21 H24 N2 O2 S'
_chemical_formula_weight         368.48
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-06
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
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_cell_measurement_reflns_used    3181
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      69.5210
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_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
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_diffrn_measurement_details
;
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -73.00  -46.00   1.0000    1.0000
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  3 omega  -29.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   16.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega  -20.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -14.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 84

  7 omega   24.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  -15.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   78.00  103.00   1.0000    1.5000
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 10 omega   64.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 11 omega   58.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 52

 12 omega   53.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 13 omega   35.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 14 omega   81.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 15 omega   57.00   84.00   1.0000    1.5000
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 16 omega  100.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 17 omega   39.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 18 omega   36.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 19 omega   66.00  101.00   1.0000    1.5000
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 20 omega   85.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 21 omega  141.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 22 omega   54.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 23 omega  -52.00  -26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 24 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega   34.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 40

 26 omega   41.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 43

 27 omega  146.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 28 omega   40.00   66.00   1.0000    1.5000
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 29 omega   96.00  124.00   1.0000    1.5000
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 30 omega   74.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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;
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_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      0.0838378000
_diffrn_orient_matrix_UB_13      0.0414358000
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_diffrn_orient_matrix_UB_22      -0.1073440000
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_diffrn_orient_matrix_UB_32      0.0121129000
_diffrn_orient_matrix_UB_33      -0.1515905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_number            8739
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_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         4.688
_diffrn_source                   'SuperNova (Cu) X-ray Source'
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_exptl_absorpt_correction_T_min  0.31457
_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
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_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         3345
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1414P)^2^+0.3041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_block           zhenn_1015
_cod_depositor_comments
'Adding full bibliography for 4038476--4038478.cif.'
_cod_original_cell_volume        1956.03(10)
_cod_database_code               4038478
_shelx_shelxl_version_number     2018/3
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_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8AA) \\sim Ueq, Uanis(C7AA) \\sim Ueq, Uanis(C6AA) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H6A(0.5) H6B(0.5) N7(0.5) O11(0.5) C12(0.5) H12(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) O15(0.5) C18(0.5) C19(0.5)
 C20(0.5) H20A(0.5) H20B(0.5) C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5)
 H22B(0.5) C23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5) H26A(0.5)
 H26B(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5) C1(0.5) H1A(0.5) H1B(0.5)
 C0AA(0.5) H0AA(0.5) H0AB(0.5) C1AA(0.5) N3AA(0.5) O2AA(0.5) C4AA(0.5)
 H4AA(0.5) H4AB(0.5) C5AA(0.5) C8AA(0.5) H8AA(0.5) C7AA(0.5) H7AA(0.5)
 C9AA(0.5) C6AA(0.5) H6AA(0.5) O0BA(0.5) C1BA(0.5) H1BA(0.5) H1BB(0.5)
 C2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5) C0BA(0.5) H0BA(0.5) H0BB(0.5)
 H0BC(0.5) H3AC(0.5) H3AD(0.5) H3AA(0.5) H3AB(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C26(H26A,H26B), C1(H1A,H1B), C0AA(H0AA,H0AB), C4AA(H4AA,H4AB),
 C1BA(H1BA,H1BB), C3AA(H3AC,H3AD), C3AA(H3AA,H3AB)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6A), C6(H6B), C8(H8), C9(H9), C12(H12), C16(H16), C24(H24),
 C25(H25), C27(H27), C28(H28), C8AA(H8AA), C7AA(H7AA), C6AA(H6AA)
4.c Idealised Me refined as rotating group:
 C2AA(H2AA,H2AB,H2AC), C0BA(H0BA,H0BB,H0BC)
;
_shelx_res_checksum              27735
_shelx_hkl_checksum              66460
_olex2_date_sample_data_collection 2019-10-16
_olex2_submission_special_instructions 'No special instructions were received'