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_4514808
_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         'C18 H10 S2'
_chemical_formula_sum            'C18 H10 S2'
_chemical_formula_weight         290.38
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.496(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.95493(11)
_cell_length_b                   12.7072(3)
_cell_length_c                   25.5848(7)
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    295.49(18)
_cell_measurement_theta_max      72.7160
_cell_measurement_theta_min      3.8410
_cell_volume                     1285.35(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.49(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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    -66.00  35.00   1.00    2.01    --  -36.29  19.00-150.00  101
  2  \w   -105.00 -17.00   1.00    2.01    --  -36.29 -38.00   0.00   88
  3  \w     23.00  90.00   1.00    2.01    --   36.29-125.00  59.00   67
  4  \w      1.00  75.00   1.00    2.01    --   36.29 -99.00-120.00   74
  5  \w    -31.00  53.00   1.00    2.01    --   36.29 -57.00  90.00   84
  6  \w     39.00 130.00   1.00    8.04    --  108.71 -30.00  60.00   91
  7  \w     39.00 115.00   1.00    8.04    --  108.71-111.00  30.00   76
  8  \w     39.00 130.00   1.00    8.04    --  108.71 -30.00 -30.00   91
  9  \w     37.00 147.00   1.00    8.04    --  108.71 -15.00-150.00  110
 10  \w     41.00 135.00   1.00    8.04    --  108.71 -77.00  60.00   94
 11  \w   -104.00 -10.00   1.00    2.01    --  -36.29 -77.00 -90.00   94
 12  \w     20.00 104.00   1.00    2.01    --   36.29  57.00 120.00   84
 13  \w    -31.00  53.00   1.00    2.01    --   36.29 -57.00 -60.00   84
 14  \w     10.00  60.00   1.00    2.01    --   36.29  77.00   0.00   50
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0654526000
_diffrn_orient_matrix_UB_12      -0.0194576000
_diffrn_orient_matrix_UB_13      0.0588422000
_diffrn_orient_matrix_UB_21      -0.0201445000
_diffrn_orient_matrix_UB_22      0.1193005000
_diffrn_orient_matrix_UB_23      0.0102401000
_diffrn_orient_matrix_UB_31      -0.3834817000
_diffrn_orient_matrix_UB_32      -0.0096021000
_diffrn_orient_matrix_UB_33      0.0078969000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6515
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.775
_diffrn_reflns_theta_min         3.884
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0575
_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^)+(0.1035P)^2^+0.2600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2208
_reflns_number_total             2492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01426_si_004.cif
_cod_data_source_block           ysp-4211
_cod_original_cell_volume        1285.36(6)
_cod_database_code               4514808
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
;
_shelx_res_checksum              18098
_shelx_hkl_checksum              36222
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-11-27
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.598
_oxdiff_exptl_absorpt_empirical_full_min 0.659