#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:25:27 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257365 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/70/1557067.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1557067
loop_
_publ_author_name
'Bürger, Marcel'
'Loch, Maximilian N.'
'Jones, Peter G.'
'Werz, Daniel B.'
_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            'C10 H7 N S'
_chemical_formula_weight         173.23
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_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                68.861(8)
_cell_angle_beta                 73.292(8)
_cell_angle_gamma                84.246(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9027(6)
_cell_length_b                   7.3743(6)
_cell_length_c                   9.3503(7)
_cell_measurement_reflns_used    7083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8490
_cell_measurement_theta_min      3.0660
_cell_volume                     425.18(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22785
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.97
_diffrn_reflns_theta_min         2.43
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.1941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2286
_reflns_number_total             2532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc04569d2.cif
_cod_data_source_block           thiete
_cod_depositor_comments
;Adding full bibliography for 1557060--1557069.cif.

 Adding full bibliography for 1557060--1557069.cif.
;
_cod_original_cell_volume        425.18(6)
_cod_database_code               1557067
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6813(2) 0.27485(17) 0.11670(14) 0.0235(3) Uani 1 1 d .
H1 H 0.7089 0.2884 0.0078 0.028 Uiso 1 1 calc R
C2 C 0.83488(19) 0.21287(17) 0.19396(14) 0.0217(2) Uani 1 1 d .
H2 H 0.9655 0.1862 0.1364 0.026 Uiso 1 1 calc R
C3 C 0.79934(17) 0.18986(16) 0.35292(13) 0.0177(2) Uani 1 1 d .
H3 H 0.9041 0.1473 0.4047 0.021 Uiso 1 1 calc R
C4 C 0.60643(16) 0.23031(15) 0.43604(12) 0.0147(2) Uani 1 1 d .
C5 C 0.45395(17) 0.29421(15) 0.35718(13) 0.0165(2) Uani 1 1 d .
C6 C 0.4899(2) 0.31668(16) 0.19669(13) 0.0210(2) Uani 1 1 d .
H6 H 0.3860 0.3594 0.1440 0.025 Uiso 1 1 calc R
C7 C 0.53091(17) 0.21426(15) 0.60136(12) 0.0152(2) Uani 1 1 d .
C8 C 0.33189(17) 0.26385(15) 0.64455(13) 0.0164(2) Uani 1 1 d .
C9 C 0.65256(17) 0.15056(16) 0.71072(13) 0.0183(2) Uani 1 1 d .
C10 C 0.20834(18) 0.26248(17) 0.80485(14) 0.0211(2) Uani 1 1 d .
H10A H 0.2792 0.1887 0.8850 0.032 Uiso 1 1 calc R
H10B H 0.0769 0.2016 0.8309 0.032 Uiso 1 1 calc R
H10C H 0.1879 0.3963 0.8039 0.032 Uiso 1 1 calc R
N1 N 0.75174(17) 0.09893(17) 0.79757(13) 0.0258(2) Uani 1 1 d .
S1 S 0.22770(4) 0.33266(4) 0.48490(3) 0.01811(9) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.97(11)
C3 C2 C1 120.99(11)
C2 C3 C4 118.87(11)
C3 C4 C5 119.74(10)
C3 C4 C7 129.41(10)
C5 C4 C7 110.84(10)
C6 C5 C4 121.31(11)
C6 C5 S1 127.30(9)
C4 C5 S1 111.38(8)
C1 C6 C5 118.11(11)
C8 C7 C9 122.76(10)
C8 C7 C4 114.16(10)
C9 C7 C4 123.08(10)
C7 C8 C10 127.68(11)
C7 C8 S1 111.22(8)
C10 C8 S1 121.10(9)
N1 C9 C7 179.36(13)
C8 S1 C5 92.40(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3845(18)
C1 C2 1.3997(18)
C2 C3 1.3837(16)
C3 C4 1.3996(15)
C4 C5 1.4035(16)
C4 C7 1.4465(14)
C5 C6 1.3985(15)
C5 S1 1.7403(12)
C7 C8 1.3678(15)
C7 C9 1.4281(15)
C8 C10 1.4933(15)
C8 S1 1.7323(12)
C9 N1 1.1478(16)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 0.61(18)
C1 C2 C3 C4 -0.21(17)
C2 C3 C4 C5 -0.41(16)
C2 C3 C4 C7 178.67(11)
C3 C4 C5 C6 0.66(16)
C7 C4 C5 C6 -178.58(10)
C3 C4 C5 S1 179.43(8)
C7 C4 C5 S1 0.19(11)
C2 C1 C6 C5 -0.36(17)
C4 C5 C6 C1 -0.28(17)
S1 C5 C6 C1 -178.83(9)
C3 C4 C7 C8 -179.24(11)
C5 C4 C7 C8 -0.09(13)
C3 C4 C7 C9 0.22(18)
C5 C4 C7 C9 179.37(10)
C9 C7 C8 C10 0.23(18)
C4 C7 C8 C10 179.70(10)
C9 C7 C8 S1 -179.51(8)
C4 C7 C8 S1 -0.05(12)
C7 C8 S1 C5 0.13(9)
C10 C8 S1 C5 -179.63(9)
C6 C5 S1 C8 178.49(11)
C4 C5 S1 C8 -0.18(8)
