Short Synthesis of Sulfur Analogues of Polyaromatic Hydrocarbons through Three Palladium-Catalyzed C-H Bond Arylations.
Hagui, Wided; Besbes, Néji; Srasra, Ezzeddine; Roisnel, Thierry; Soulé, Jean-François; Doucet, Henri; Organic letters 18 (2016) 4182–4185; doi:10.1021/acs.orglett.6b01735

data_1543963
_publ_section_title
;
 Short Synthesis of Sulfur Analogues of Polyaromatic Hydrocarbons through
 Three Palladium-Catalyzed C-H Bond Arylations.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4182
_journal_page_last               4185
_journal_paper_doi               10.1021/acs.orglett.6b01735
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H11 N S'
_chemical_formula_sum            'C18 H11 N S'
_chemical_formula_weight         273.34
_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
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_cell_angle_beta                 98.536(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_theta_min      2.89
_cell_measurement_wavelength     0.71073
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_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
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_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
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_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1050
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_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10490
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_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.944
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
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_refine_diff_density_max         0.377
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0424P)^2^+1.6517P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                1900
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01735_si_001.cif
_cod_data_source_block           WH_P4_26b
_cod_depositor_comments          'Adding full bibliography for 1543963.cif.'
_cod_original_cell_volume        1252.3(4)
_cod_database_code               1543963
_shelx_res_checksum              70998
_shelx_hkl_checksum              71092