#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:25:27 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257365 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/70/1557063.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_1557063
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            'C11 H9 N O S'
_chemical_formula_weight         203.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                90.00
_cell_angle_beta                 104.425(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9143(2)
_cell_length_b                   7.26579(18)
_cell_length_c                   12.4737(2)
_cell_measurement_reflns_used    11164
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0740
_cell_measurement_theta_min      4.1720
_cell_volume                     957.99(3)
_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_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 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20246
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         75.86
_diffrn_reflns_theta_min         4.18
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79147
_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    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0307
_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/[σ²(Fo²)+(0.0472P)²+0.3528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                1791
_reflns_number_total             1990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc04569d2.cif
_cod_data_source_block           hamm
_cod_depositor_comments
;Adding full bibliography for 1557060--1557069.cif.

 Adding full bibliography for 1557060--1557069.cif.
;
_cod_original_cell_volume        957.99(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1557063
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.72738(13) 0.0739(2) 0.20909(11) 0.0191(3) Uani 1 1 d .
C2 C 0.72333(13) 0.13049(19) 0.31522(12) 0.0186(3) Uani 1 1 d .
C3 C 0.46815(13) 0.15354(19) 0.22728(11) 0.0181(3) Uani 1 1 d .
C4 C 0.51816(13) 0.1716(2) 0.12572(11) 0.0198(3) Uani 1 1 d .
H4A H 0.4485 0.1494 0.0591 0.024 Uiso 1 1 calc R
H4B H 0.5493 0.2986 0.1213 0.024 Uiso 1 1 calc R
C5 C 0.84289(14) 0.0372(2) 0.18558(12) 0.0239(3) Uani 1 1 d .
H5 H 0.8453 -0.0031 0.1137 0.029 Uiso 1 1 calc R
C6 C 0.95432(13) 0.0590(2) 0.26655(13) 0.0258(3) Uani 1 1 d .
H6 H 1.0330 0.0325 0.2503 0.031 Uiso 1 1 calc R
C7 C 0.95158(14) 0.1200(2) 0.37200(13) 0.0243(3) Uani 1 1 d .
H7 H 1.0283 0.1375 0.4270 0.029 Uiso 1 1 calc R
C8 C 0.83648(14) 0.1548(2) 0.39620(12) 0.0214(3) Uani 1 1 d .
H8 H 0.8345 0.1953 0.4681 0.026 Uiso 1 1 calc R
C9 C 0.34419(13) 0.14024(19) 0.22494(11) 0.0190(3) Uani 1 1 d .
C10 C 0.30901(13) 0.1131(2) 0.32759(12) 0.0201(3) Uani 1 1 d .
C11 C 0.23524(14) 0.1504(2) 0.12315(12) 0.0230(3) Uani 1 1 d .
H11A H 0.2668 0.1873 0.0594 0.035 Uiso 1 1 calc R
H11B H 0.1734 0.2411 0.1350 0.035 Uiso 1 1 calc R
H11C H 0.1947 0.0295 0.1090 0.035 Uiso 1 1 calc R
N1 N 0.27838(11) 0.08595(19) 0.40787(10) 0.0257(3) Uani 1 1 d .
O1 O 0.61914(9) 0.04384(14) 0.12685(8) 0.0207(2) Uani 1 1 d .
S1 S 0.58052(3) 0.15677(5) 0.35532(3) 0.01998(13) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 C1 C5 117.90(12)
O1 C1 C2 121.96(12)
C5 C1 C2 120.06(13)
C1 C2 C8 119.40(13)
C1 C2 S1 122.67(11)
C8 C2 S1 117.76(11)
C9 C3 C4 124.06(13)
C9 C3 S1 119.36(11)
C4 C3 S1 116.56(10)
O1 C4 C3 111.93(11)
C6 C5 C1 120.19(13)
C5 C6 C7 120.23(13)
C8 C7 C6 119.78(14)
C7 C8 C2 120.31(14)
C3 C9 C10 118.62(13)
C3 C9 C11 126.16(13)
C10 C9 C11 115.22(12)
N1 C10 C9 177.53(16)
C1 O1 C4 114.74(10)
C3 S1 C2 101.96(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3755(16)
C1 C5 1.3896(19)
C1 C2 1.3973(19)
C2 C8 1.398(2)
C2 S1 1.7620(14)
C3 C9 1.349(2)
C3 C4 1.5049(19)
C3 S1 1.7549(14)
C4 O1 1.4381(17)
C5 C6 1.383(2)
C6 C7 1.395(2)
C7 C8 1.386(2)
C9 C10 1.4390(19)
C9 C11 1.5098(18)
C10 N1 1.1489(19)
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
O1 C1 C2 C8 178.52(13)
C5 C1 C2 C8 1.9(2)
O1 C1 C2 S1 3.3(2)
C5 C1 C2 S1 -173.29(11)
C9 C3 C4 O1 -131.24(14)
S1 C3 C4 O1 50.53(14)
O1 C1 C5 C6 -177.76(13)
C2 C1 C5 C6 -1.0(2)
C1 C5 C6 C7 -0.7(2)
C5 C6 C7 C8 1.4(2)
C6 C7 C8 C2 -0.5(2)
C1 C2 C8 C7 -1.1(2)
S1 C2 C8 C7 174.27(11)
C4 C3 C9 C10 176.50(13)
S1 C3 C9 C10 -5.32(18)
C4 C3 C9 C11 -3.3(2)
S1 C3 C9 C11 174.93(11)
C5 C1 O1 C4 -145.25(13)
C2 C1 O1 C4 38.03(18)
C3 C4 O1 C1 -65.75(15)
C9 C3 S1 C2 169.19(11)
C4 C3 S1 C2 -12.49(12)
C1 C2 S1 C3 -14.24(14)
C8 C2 S1 C3 170.52(11)
