#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/55/4035527.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_4035527
loop_
_publ_author_name
'Higashimae, Shinya'
'Kurata, Daichi'
'Kawaguchi, Shin-Ichi'
'Kodama, Shintaro'
'Sonoda, Motohiro'
'Nomoto, Akihiro'
'Ogawa, Akiya'
_publ_section_title
;
 Palladium-Catalyzed Cyanothiolation of Internal Alkynes Using Organic
 Disulfides and tert-Butyl Isocyanide.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5267
_journal_page_last               5273
_journal_paper_doi               10.1021/acs.joc.8b00052
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H15 N S'
_chemical_formula_sum            'C21 H15 N S'
_chemical_formula_weight         313.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.8705(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.07707(17)
_cell_length_b                   15.3472(3)
_cell_length_c                   13.2213(3)
_cell_measurement_reflns_used    13359
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.04
_cell_volume                     1635.18(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.527
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656.00
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0421P)²+0.6176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3515
_reflns_number_total             3749
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo8b00052_si_003.cif
_cod_data_source_block           Higashimae-601
_cod_database_code               4035527
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.64337(3) 0.39873(2) 0.52748(2) 0.02038(9) Uani 1 1 d . .
N1 N 0.81395(13) 0.54424(7) 0.35787(7) 0.0247(2) Uani 1 1 d . .
C1 C 0.72440(12) 0.48530(7) 0.60268(7) 0.0155(2) Uani 1 1 d . .
C2 C 0.77613(12) 0.55577(7) 0.55040(7) 0.0153(2) Uani 1 1 d . .
C3 C 0.79519(13) 0.54671(7) 0.44321(8) 0.0180(2) Uani 1 1 d . .
C4 C 0.67282(13) 0.30183(7) 0.59902(7) 0.0166(2) Uani 1 1 d . .
C5 C 0.54630(14) 0.24028(7) 0.58533(8) 0.0210(2) Uani 1 1 d . .
H5 H 0.448833 0.253378 0.543853 0.025 Uiso 1 1 calc R U
C6 C 0.56363(15) 0.15976(7) 0.63266(9) 0.0245(2) Uani 1 1 d . .
H6 H 0.478027 0.117520 0.623054 0.029 Uiso 1 1 calc R U
C7 C 0.70503(16) 0.14059(8) 0.69383(9) 0.0259(2) Uani 1 1 d . .
H7 H 0.716283 0.085450 0.726215 0.031 Uiso 1 1 calc R U
C8 C 0.83035(15) 0.20242(8) 0.70761(9) 0.0248(2) Uani 1 1 d . .
H8 H 0.926970 0.189384 0.749878 0.030 Uiso 1 1 calc R U
C9 C 0.81559(13) 0.28318(7) 0.66007(8) 0.0200(2) Uani 1 1 d . .
H9 H 0.901879 0.325080 0.669167 0.024 Uiso 1 1 calc R U
C10 C 0.72328(12) 0.48161(6) 0.71446(8) 0.0158(2) Uani 1 1 d . .
C11 C 0.59087(13) 0.44485(7) 0.76259(8) 0.0186(2) Uani 1 1 d . .
H11 H 0.497065 0.423156 0.723228 0.022 Uiso 1 1 calc R U
C12 C 0.59601(14) 0.43993(7) 0.86762(9) 0.0218(2) Uani 1 1 d . .
H12 H 0.506431 0.414150 0.899789 0.026 Uiso 1 1 calc R U
C13 C 0.73159(14) 0.47255(8) 0.92584(8) 0.0229(2) Uani 1 1 d . .
H13 H 0.734547 0.469491 0.997701 0.027 Uiso 1 1 calc R U
C14 C 0.86310(14) 0.50975(7) 0.87845(8) 0.0217(2) Uani 1 1 d . .
H14 H 0.955296 0.532769 0.918186 0.026 Uiso 1 1 calc R U
C15 C 0.86030(13) 0.51340(7) 0.77348(8) 0.0179(2) Uani 1 1 d . .
H15 H 0.951744 0.537570 0.741623 0.022 Uiso 1 1 calc R U
C16 C 0.80124(12) 0.64636(7) 0.58826(7) 0.0159(2) Uani 1 1 d . .
C17 C 0.70114(13) 0.68211(7) 0.65974(8) 0.0199(2) Uani 1 1 d . .
H17 H 0.617969 0.647477 0.687564 0.024 Uiso 1 1 calc R U
C18 C 0.72290(15) 0.76811(8) 0.69020(9) 0.0253(2) Uani 1 1 d . .
H18 H 0.655891 0.791591 0.739889 0.030 Uiso 1 1 calc R U
C19 C 0.84167(16) 0.82025(8) 0.64878(9) 0.0279(3) Uani 1 1 d . .
H19 H 0.855543 0.879163 0.669712 0.033 Uiso 1 1 calc R U
C20 C 0.93956(16) 0.78562(8) 0.57680(9) 0.0286(3) Uani 1 1 d . .
H20 H 1.020433 0.820993 0.547769 0.034 Uiso 1 1 calc R U
C21 C 0.91984(14) 0.69929(8) 0.54688(9) 0.0229(2) Uani 1 1 d . .
H21 H 0.987928 0.675983 0.497646 0.027 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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
C1 S1 C4 107.52(5)
C2 C1 C10 123.99(9)
C2 C1 S1 115.31(8)
C10 C1 S1 120.57(7)
C1 C2 C3 118.55(9)
C1 C2 C16 127.60(9)
C3 C2 C16 113.56(9)
N1 C3 C2 176.09(11)
C9 C4 C5 120.47(10)
C9 C4 S1 123.98(8)
C5 C4 S1 115.40(8)
C6 C5 C4 119.59(10)
C6 C5 H5 120.2
C4 C5 H5 120.2
C7 C6 C5 120.41(11)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C8 119.71(11)
C6 C7 H7 120.1
C8 C7 H7 120.1
C7 C8 C9 120.62(11)
C7 C8 H8 119.7
C9 C8 H8 119.7
C8 C9 C4 119.18(10)
C8 C9 H9 120.4
C4 C9 H9 120.4
C15 C10 C11 119.16(9)
C15 C10 C1 119.09(9)
C11 C10 C1 121.73(9)
C12 C11 C10 120.29(10)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 120.26(10)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C14 119.72(10)
C12 C13 H13 120.1
C14 C13 H13 120.1
C15 C14 C13 120.36(10)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C10 120.19(10)
C14 C15 H15 119.9
C10 C15 H15 119.9
C21 C16 C17 118.72(10)
C21 C16 C2 119.60(9)
C17 C16 C2 121.54(9)
C18 C17 C16 120.15(10)
C18 C17 H17 119.9
C16 C17 H17 119.9
C17 C18 C19 120.71(11)
C17 C18 H18 119.6
C19 C18 H18 119.6
C20 C19 C18 119.44(11)
C20 C19 H19 120.3
C18 C19 H19 120.3
C19 C20 C21 120.16(11)
C19 C20 H20 119.9
C21 C20 H20 119.9
C20 C21 C16 120.81(11)
C20 C21 H21 119.6
C16 C21 H21 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7591(10)
S1 C4 1.7698(10)
N1 C3 1.1491(15)
C1 C2 1.3642(14)
C1 C10 1.4796(14)
C2 C3 1.4425(14)
C2 C16 1.4869(14)
C4 C9 1.3919(15)
C4 C5 1.3945(15)
C5 C6 1.3880(16)
C5 H5 0.9500
C6 C7 1.3857(17)
C6 H6 0.9500
C7 C8 1.3904(17)
C7 H7 0.9500
C8 C9 1.3912(15)
C8 H8 0.9500
C9 H9 0.9500
C10 C15 1.3983(14)
C10 C11 1.3997(14)
C11 C12 1.3885(15)
C11 H11 0.9500
C12 C13 1.3886(16)
C12 H12 0.9500
C13 C14 1.3916(16)
C13 H13 0.9500
C14 C15 1.3877(15)
C14 H14 0.9500
C15 H15 0.9500
C16 C21 1.3956(15)
C16 C17 1.3968(15)
C17 C18 1.3875(16)
C17 H17 0.9500
C18 C19 1.3898(18)
C18 H18 0.9500
C19 C20 1.3838(18)
C19 H19 0.9500
C20 C21 1.3888(16)
C20 H20 0.9500
C21 H21 0.9500
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
C4 S1 C1 C2 153.80(8)
C4 S1 C1 C10 -30.23(9)
C10 C1 C2 C3 170.67(9)
S1 C1 C2 C3 -13.52(13)
C10 C1 C2 C16 -15.87(16)
S1 C1 C2 C16 159.94(8)
C1 S1 C4 C9 -40.34(10)
C1 S1 C4 C5 144.05(8)
C9 C4 C5 C6 -0.30(16)
S1 C4 C5 C6 175.48(8)
C4 C5 C6 C7 0.48(17)
C5 C6 C7 C8 -0.15(18)
C6 C7 C8 C9 -0.38(18)
C7 C8 C9 C4 0.56(17)
C5 C4 C9 C8 -0.22(16)
S1 C4 C9 C8 -175.62(8)
C2 C1 C10 C15 -43.73(14)
S1 C1 C10 C15 140.67(8)
C2 C1 C10 C11 138.18(11)
S1 C1 C10 C11 -37.43(13)
C15 C10 C11 C12 -0.13(15)
C1 C10 C11 C12 177.97(10)
C10 C11 C12 C13 0.89(16)
C11 C12 C13 C14 -0.43(17)
C12 C13 C14 C15 -0.80(17)
C13 C14 C15 C10 1.57(16)
C11 C10 C15 C14 -1.10(15)
C1 C10 C15 C14 -179.25(10)
C1 C2 C16 C21 150.67(11)
C3 C2 C16 C21 -35.60(13)
C1 C2 C16 C17 -33.73(16)
C3 C2 C16 C17 140.00(10)
C21 C16 C17 C18 -1.47(16)
C2 C16 C17 C18 -177.12(10)
C16 C17 C18 C19 1.31(17)
C17 C18 C19 C20 -0.33(18)
C18 C19 C20 C21 -0.47(19)
C19 C20 C21 C16 0.29(18)
C17 C16 C21 C20 0.68(16)
C2 C16 C21 C20 176.41(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329254
