From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes
Bürger, Marcel; Loch, Maximilian N.; Jones, Peter G.; Werz, Daniel B.; Chemical Science 11 (2020) 1912–1917; doi:10.1039/C9SC04569D

data_1557068
_publ_section_title
;
 From 1,2-difunctionalisation to cyanide-transfer cascades -- Pd-catalysed
 cyanosulfenylation of internal (oligo)alkynes
;
_journal_issue                   7
_journal_name_full               'Chemical Science'
_journal_page_first              1912
_journal_page_last               1917
_journal_paper_doi               10.1039/C9SC04569D
_journal_volume                  11
_journal_year                    2020
_chemical_formula_sum            'C16 H11 N O S'
_chemical_formula_weight         265.32
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.2557(2)
_cell_length_b                   9.5626(2)
_cell_length_c                   21.5616(4)
_cell_measurement_reflns_used    24382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0140
_cell_measurement_theta_min      5.4530
_cell_volume                     2526.94(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            49411
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.08
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular tablet'
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.8618P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2422
_reflns_number_total             2638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc04569d2.cif
_cod_data_source_block           veji
_cod_depositor_comments
;Adding full bibliography for 1557060--1557069.cif.

 Adding full bibliography for 1557060--1557069.cif.
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_cod_database_code               1557068