Rh/Ag-Mediated Peri-Selective Heteroarylation/Single Electron Transfer Annulation Cascade of 1-(Methylthio)naphthalenes and Analogues: Road Less Traveled to Benzo[de]thioacenes
Yang, Shiping; Cheng, Rui; Zhang, Min; Bin, Zhengyang; You, Jingsong; ACS Catalysis 9 (2019) 6188–; doi:10.1021/acscatal.9b01426

data_4514805
_publ_section_title
;
 Rh/Ag-Mediated Peri-Selective Heteroarylation/Single Electron Transfer
 Annulation Cascade of 1-(Methylthio)naphthalenes and Analogues: Road Less
 Traveled to Benzo[de]thioacenes
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6188
_journal_paper_doi               10.1021/acscatal.9b01426
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C19 H14 S2'
_chemical_formula_sum            'C19 H14 S2'
_chemical_formula_weight         306.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                78.352(8)
_cell_angle_beta                 79.150(8)
_cell_angle_gamma                72.944(9)
_cell_formula_units_Z            2
_cell_length_a                   7.9503(8)
_cell_length_b                   8.3038(8)
_cell_length_c                   12.6012(11)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    295.9(6)
_cell_measurement_theta_max      71.9130
_cell_measurement_theta_min      6.2340
_cell_volume                     771.51(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  -30.0000 84

  2 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000 -180.0000 67

  3 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000 -150.0000 88

  4 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000  -60.0000 88

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000 -150.0000 84

  6 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000   90.0000 84

  7 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000  150.0000 84

  8 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000  -60.0000 74

  9 omega   38.00   91.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 10 omega   91.00  176.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 11 omega   38.00  116.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 78

 12 omega   38.00   91.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 13 omega   40.00   98.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 14 omega   39.00  109.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 15 omega  100.00  178.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 78

 16 omega   37.00  146.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -150.0000 109

 17 omega   38.00   91.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 18 omega   38.00   91.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 19 omega   40.00   98.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 20 omega   39.00  109.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 21 omega   41.00  126.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 85

 22 omega   40.00   98.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 23 omega   90.00  175.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 24 omega   38.00   91.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 25 omega   38.00  116.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 78

 26 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000   60.0000 88

 27 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000 -150.0000 95

 28 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000   30.0000 95

 29 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  150.0000 84

 30 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  -60.0000 95

 31 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  120.0000 95

 32 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000    0.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1268594000
_diffrn_orient_matrix_UB_12      0.0313519000
_diffrn_orient_matrix_UB_13      0.0674434000
_diffrn_orient_matrix_UB_21      0.1605742000
_diffrn_orient_matrix_UB_22      -0.0910559000
_diffrn_orient_matrix_UB_23      -0.0754874000
_diffrn_orient_matrix_UB_31      -0.0001575000
_diffrn_orient_matrix_UB_32      0.1712518000
_diffrn_orient_matrix_UB_33      -0.0750747000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.287
_diffrn_reflns_theta_min         5.642
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.022
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.085
_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     211
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0688
_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^)+(0.1398P)^2^+0.2021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2696
_reflns_number_total             2983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01426_si_002.cif
_cod_data_source_block           ysp-4212
_cod_database_code               4514805
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(S0AB)=1-FVAR(1)
 Sof(S0AA)=FVAR(1)
 Sof(C0AB)=Sof(H0AB)=1-FVAR(2)
 Sof(C0AA)=Sof(H0AA)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C0AA(H0AA), C0AB(H0AB)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'