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_4514804
_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         'C34 H36 O S2'
_chemical_formula_sum            'C34 H36 O S2'
_chemical_formula_weight         524.75
_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             2019-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.451(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8072(5)
_cell_length_b                   13.6963(4)
_cell_length_c                   17.6483(6)
_cell_measurement_reflns_used    5529
_cell_measurement_temperature    180
_cell_measurement_theta_max      72.6570
_cell_measurement_theta_min      4.1770
_cell_volume                     2900.59(19)
_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      180
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

  2 omega  -31.00   53.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

  3 omega    1.00   75.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  4 omega    1.00   75.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -90.0000 74

  5 omega    0.00   26.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   94.0000 -102.7410 26

  6 omega  -33.00  106.00   1.0000    2.9800
omega____ theta____ kappa____ phi______ frames
    -       36.2921    0.0000  -60.0000 139

  7 omega   38.00   91.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

  8 omega   40.00   98.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

  9 omega   38.00   91.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 10 omega   40.00   98.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 11 omega   91.00  176.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 12 omega   38.00   91.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 13 omega   91.00  176.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 14 omega   37.00  112.00   1.0000   11.9300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 75
;
_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      -0.1223883000
_diffrn_orient_matrix_UB_12      0.0333273000
_diffrn_orient_matrix_UB_13      -0.0259220000
_diffrn_orient_matrix_UB_21      0.0312679000
_diffrn_orient_matrix_UB_22      0.0718344000
_diffrn_orient_matrix_UB_23      0.0715958000
_diffrn_orient_matrix_UB_31      0.0229425000
_diffrn_orient_matrix_UB_32      0.0798980000
_diffrn_orient_matrix_UB_33      -0.0536644000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12829
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.820
_diffrn_reflns_theta_min         4.191
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60589
_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    1.202
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5606
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1194P)^2^+0.8237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1712
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4967
_reflns_number_total             5606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01426_si_006.cif
_cod_data_source_block           ysp-4449-180k
_cod_original_cell_volume        2900.57(18)
_cod_database_code               4514804
_reflns_odcompleteness_completeness 99.56
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.c Idealised Me refined as rotating group:
 C00V(H00E,H00F,H00G), C00W(H00I,H00K,H00O), C00X(H00U,H00V,H00W), C00Y(H00X,
 H00Y,H), C00Z(H00Z,HA,HB), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              30927
_shelx_hkl_checksum              25749
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-11
_olex2_submission_special_instructions 'No special instructions were received'