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_4514806
_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 O S2'
_chemical_formula_sum            'C19 H14 O S2'
_chemical_formula_weight         322.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.977(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6530(4)
_cell_length_b                   5.92231(13)
_cell_length_c                   33.4022(9)
_cell_measurement_reflns_used    7954
_cell_measurement_temperature    291.3(8)
_cell_measurement_theta_max      72.4660
_cell_measurement_theta_min      5.4670
_cell_volume                     3182.36(14)
_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      291.3(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -57.0000   30.0000 84

  2 omega   23.00   89.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171 -125.0000  150.0000 66

  3 omega   -1.00   25.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   95.0000 -100.0275 26

  4 omega    1.00   75.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -99.0000  -90.0000 74

  5 omega   23.00   89.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171 -125.0000   30.0000 66

  6 omega  -31.00   53.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -57.0000  150.0000 84

  7 omega    9.00  103.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   77.0000 -180.0000 94

  8 omega    1.00   75.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -99.0000  -30.0000 74

  9 omega   17.00  105.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   38.0000 -180.0000 88

 10 omega   17.00  105.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   38.0000   30.0000 88

 11 omega  -35.00   65.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -19.0000 -150.0000 100

 12 omega   38.00  116.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 78

 13 omega   38.00   91.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 14 omega   39.00  109.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 15 omega   87.00  178.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 16 omega  100.00  178.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 78

 17 omega   40.00   98.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 18 omega   38.00   91.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 19 omega   39.00  109.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 20 omega   39.00  109.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 21 omega   38.00   91.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 22 omega   38.00   91.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 23 omega   38.00   91.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 24 omega   91.00  176.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 25 omega   39.00  109.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 26 omega   40.00   98.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 27 omega   40.00   98.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 28 omega   38.00  116.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 29 omega   87.00  178.00   1.0000   28.4750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

 30 omega    0.00   26.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   94.0000   16.6958 26

 31 omega   19.00  103.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   57.0000   90.0000 84

 32 omega    7.00  107.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   19.0000  -30.0000 100

 33 omega    9.00  103.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   77.0000  120.0000 94

 34 omega   19.00  103.00   1.0000    7.1200
omega____ theta____ kappa____ phi______ frames
    -       35.9171   57.0000  -60.0000 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      0.0123382000
_diffrn_orient_matrix_UB_12      -0.0061608000
_diffrn_orient_matrix_UB_13      0.0473203000
_diffrn_orient_matrix_UB_21      0.0519808000
_diffrn_orient_matrix_UB_22      -0.2171964000
_diffrn_orient_matrix_UB_23      0.0025308000
_diffrn_orient_matrix_UB_31      0.0794677000
_diffrn_orient_matrix_UB_32      0.1429949000
_diffrn_orient_matrix_UB_33      0.0058685000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            15667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_min         5.475
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35743
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0671
_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^)+(0.0915P)^2^+6.2278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1765
_refine_ls_wR_factor_ref         0.1798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2910
_reflns_number_total             3117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01426_si_003.cif
_cod_data_source_block           ysp-dw186
_cod_database_code               4514806
_reflns_odcompleteness_completeness 99.87
_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. Rigid bond restraints
 C006, C007
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C006 \\sim C007: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
4.b Idealised Me refined as rotating group:
 C00D(H00A,H00B,H00D)
;
_shelx_res_checksum              89925
_shelx_hkl_checksum              47009
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-04
_olex2_submission_special_instructions 'No special instructions were received'