Synthesis of 3-(2-Thiopyridiyl)indoles via Ruthenium Catalyzed [2+2+2] Cycloaddition of Diynes and 3-Thiocyanatoindoles
Chowdhury, Hrishikesh; Goswami, Avijit; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01101F

data_7155708
_publ_section_title
;
 Synthesis of 3-(2-Thiopyridiyl)indoles via Ruthenium Catalyzed [2+2+2]
 Cycloaddition of Diynes and 3-Thiocyanatoindoles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01101F
_journal_year                    2017
_chemical_formula_moiety         'C31 H30 N2 O2 S'
_chemical_formula_sum            'C31 H30 N2 O2 S'
_chemical_formula_weight         494.63
_chemical_name_common            'Indole-C3-thio pyridine derivative2'
_chemical_name_systematic        'Indole-C3-thio pyridine derivative2'
_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
_audit_block_doi                 10.5517/ccdc.csd.cc1mwyq5
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-11-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.984(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5208(9)
_cell_length_b                   12.0966(7)
_cell_length_c                   12.4375(6)
_cell_measurement_reflns_used    6565
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.3
_cell_volume                     2626.1(2)
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_molecular_graphics    'Ortep, Pluton'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.233
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            56690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      1.25
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate - hexane'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0547P)^2^+1.1266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4893
_reflns_number_total             6565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01101f2.cif
_cod_data_source_block           AG_HC_365
_cod_database_code               7155708
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2014-3
_shelx_res_checksum              96378