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_4038477
_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         'C18 H17 F3 N2 O S'
_chemical_formula_sum            'C18 H17 F3 N2 O S'
_chemical_formula_weight         366.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.968(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.56093(16)
_cell_length_b                   10.6632(2)
_cell_length_c                   22.1615(5)
_cell_measurement_reflns_used    2748
_cell_measurement_temperature    290.73(10)
_cell_measurement_theta_max      69.1520
_cell_measurement_theta_min      7.9790
_cell_volume                     1785.69(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      290.73(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -36.00 -11.00   1.00    1.00    --    0.00 107.00  90.00   25
  2  \w    -71.00   2.00   1.00    1.00    --    0.00 -38.00 -30.00   73
  3  \w      2.00  96.00   1.00    1.00    --   54.00 -99.00  60.00   94
  4  \w     60.00 121.00   1.00    1.00    --  108.00 -63.00  90.00   61
  5  \w     39.00 128.00   1.00    1.00    --  108.00 -77.00 -60.00   89
  6  \w     88.00 124.00   1.00    1.00    --   54.00  38.00-150.00   36
  7  \w     80.00 177.00   1.00    1.00    --  108.00  77.00-150.00   97
  8  \w    132.00 176.00   1.00    1.00    --  108.00 111.00-120.00   44
  9  \w    117.00 148.00   1.00    1.00    --  108.00 111.00  60.00   31
 10  \w    108.00 148.00   1.00    1.00    --  108.00  63.00 120.00   40
 11  \w    101.00 153.00   1.00    1.00    --  108.00 111.00 150.00   52
 12  \w     74.00 126.00   1.00    1.00    --  108.00 178.00   0.00   52
 13  \w     48.00 119.00   1.00    1.00    --   54.00  57.00-180.00   71
 14  \w     54.00 115.00   1.00    1.00    --  108.00-111.00 -90.00   61
 15  \w    -11.00  42.00   1.00    1.00    --   54.00 -77.00 -30.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0310508000
_diffrn_orient_matrix_UB_12      0.0964254000
_diffrn_orient_matrix_UB_13      0.0503535000
_diffrn_orient_matrix_UB_21      0.1110477000
_diffrn_orient_matrix_UB_22      -0.0807405000
_diffrn_orient_matrix_UB_23      0.0447114000
_diffrn_orient_matrix_UB_31      0.1680452000
_diffrn_orient_matrix_UB_32      0.0712680000
_diffrn_orient_matrix_UB_33      -0.0173632000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6327
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.992
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0534P)^2^+0.4255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2753
_reflns_number_total             3135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03489_si_003.cif
_cod_data_source_block           zhennian_0523
_cod_depositor_comments
'Adding full bibliography for 4038476--4038478.cif.'
_cod_original_cell_volume        1785.69(7)
_cod_database_code               4038477
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.70
_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:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
;
_shelx_res_checksum              9626
_shelx_hkl_checksum              10595
_olex2_date_sample_data_collection 2019-05-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.798