A copper-catalyzed arylation/nucleophilic addition/fragmentation/C–S bond formation cascade: synthesis of bis(arylthio)imines
Guo, Wei-Si; Wang, Yuan-Chao; Dou, Qian; Wen, Li-Rong; Li, Ming; Organic Chemistry Frontiers 4 (2017) 510–; doi:10.1039/C6QO00739B

data_1553615
_publ_section_title
;
 A copper-catalyzed arylation/nucleophilic addition/fragmentation/C--S
 bond formation cascade: synthesis of bis(arylthio)imines
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              510
_journal_paper_doi               10.1039/C6QO00739B
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C23 H19 N O2 S2'
_chemical_formula_sum            'C23 H19 N O2 S2'
_chemical_formula_weight         405.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-07-18 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.189(2)
_cell_length_b                   14.782(4)
_cell_length_c                   17.421(5)
_cell_measurement_reflns_used    6235
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4770
_cell_measurement_theta_min      1.8068
_cell_volume                     2108.8(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1316
	          2theta: -19.7250
scan:
	Number of images: 298
	           Slice: -109.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 12.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1316
	          2theta: -19.7250
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0435
_diffrn_orient_matrix_UB_12      -0.0088
_diffrn_orient_matrix_UB_13      0.1138
_diffrn_orient_matrix_UB_21      0.0290
_diffrn_orient_matrix_UB_22      -0.0591
_diffrn_orient_matrix_UB_23      -0.0157
_diffrn_orient_matrix_UB_31      0.0476
_diffrn_orient_matrix_UB_32      0.0277
_diffrn_orient_matrix_UB_33      -0.0161
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15230
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         2.714
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0260P)^2^+0.7062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4450
_reflns_number_total             4800
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00739b2.cif
_cod_data_source_block           sa4333
_cod_original_cell_volume        2108.7(10)
_cod_database_code               1553615
_diffrn_number_total             2764
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              82189
_shelx_hkl_checksum              40659
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'