data_25 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(tris-phenylsulfanyl-methyl)-pyridine' ; _chemical_name_common '25' _chemical_melting_point ? _chemical_formula_moiety 'C24 H19 N S3' _chemical_formula_sum 'C24 H19 N S3' _chemical_formula_weight 417.58 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2196(4) _cell_length_b 10.2735(7) _cell_length_c 13.8570(11) _cell_angle_alpha 92.479(4) _cell_angle_beta 106.581(4) _cell_angle_gamma 111.661(4) _cell_volume 1027.68(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 59580 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 32.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details ; Sortav, Blessing, R. H. (1995) Acta Cryst. A51, 33-38. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59580 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 32.02 _reflns_number_total 6553 _reflns_number_gt 6016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Suite (Otwinoski & Minor, 1997)' _computing_data_reduction ; 'HKL Suite (Otwinoski & Minor, 1997)' 'Sortav (Blessing, R. H. (1997) J. Appl. Cryst. 30, 421-426' ; _computing_structure_solution ; 'SIR92 Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343-350.' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material ; 'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)' ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.4469P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6553 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0780 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.51925(3) 0.79417(2) 0.292571(17) 0.01406(6) Uani 1 1 d . . . S3 S 0.69740(3) 0.97375(3) 0.162754(17) 0.01494(6) Uani 1 1 d . . . S2 S 0.52087(3) 1.07385(2) 0.304185(16) 0.01320(5) Uani 1 1 d . . . N1 N 0.32222(12) 0.78032(10) 0.05187(6) 0.01844(16) Uani 1 1 d . . . C21 C 0.95455(13) 1.22047(11) 0.29305(8) 0.01734(18) Uani 1 1 d . . . H21 H 0.8929 1.2682 0.2490 0.021 Uiso 1 1 calc R . . C9 C 0.31446(14) 0.77718(11) 0.42142(7) 0.01710(17) Uani 1 1 d . . . H9 H 0.4265 0.8430 0.4697 0.021 Uiso 1 1 calc R . . C8 C 0.31082(13) 0.73360(10) 0.32366(7) 0.01366(16) Uani 1 1 d . . . C2 C 0.32281(12) 0.87132(10) 0.12426(7) 0.01322(16) Uani 1 1 d . . . C3 C 0.16891(14) 0.90060(11) 0.12118(8) 0.01799(18) Uani 1 1 d . . . H3 H 0.1743 0.9657 0.1740 0.022 Uiso 1 1 calc R . . C20 C 0.89163(13) 1.07265(11) 0.27239(7) 0.01549(17) Uani 1 1 d . . . C19 C 0.49258(13) 1.22287(10) 0.13650(7) 0.01535(17) Uani 1 1 d . . . H19 H 0.4929 1.1473 0.0946 0.018 Uiso 1 1 calc R . . C25 C 0.98439(14) 1.00297(12) 0.33628(8) 0.01973(19) Uani 1 1 d . . . H25 H 0.9443 0.9028 0.3214 0.024 Uiso 1 1 calc R . . C23 C 1.19683(14) 1.22761(12) 0.44292(8) 0.0211(2) Uani 1 1 d . . . H23 H 1.2999 1.2802 0.5017 0.025 Uiso 1 1 calc R . . C18 C 0.48196(14) 1.34332(11) 0.09684(8) 0.01761(18) Uani 1 1 d . . . H18 H 0.4756 1.3493 0.0277 0.021 Uiso 1 1 calc R . . C24 C 1.13619(14) 1.08105(12) 0.42209(8) 0.0222(2) Uani 1 1 d . . . H24 H 1.1982 1.0338 0.4664 0.027 Uiso 1 1 calc R . . C15 C 0.50165(14) 1.32656(10) 0.29912(8) 0.01683(17) Uani 1 1 d . . . H15 H 0.5091 1.3215 0.3684 0.020 Uiso 1 1 calc R . . C11 C -0.01079(15) 0.62929(12) 0.37707(8) 0.0212(2) Uani 1 1 d . . . H11 H -0.1204 0.5939 0.3952 0.025 Uiso 1 1 calc R . . C22 C 1.10750(14) 1.29792(12) 0.37818(8) 0.01987(19) Uani 1 1 d . . . H22 H 1.1507 1.3984 0.3920 0.024 Uiso 1 1 calc R . . C14 C 0.50275(12) 1.21456(10) 0.23824(7) 0.01291(16) Uani 1 1 d . . . C12 C -0.01510(14) 0.58614(11) 0.27940(8) 0.02007(19) Uani 1 1 d . . . H12 H -0.1281 0.5222 0.2308 0.024 Uiso 1 1 calc R . . C13 C 0.14545(14) 0.63636(10) 0.25275(7) 0.01715(18) Uani 1 1 d . . . H13 H 0.1429 0.6048 0.1867 0.021 Uiso 1 1 calc R . . C4 C 0.00729(15) 0.83220(13) 0.03888(9) 0.0235(2) Uani 1 1 d . . . H4 H -0.0999 0.8500 0.0344 0.028 Uiso 1 1 calc R . . C10 C 0.15399(15) 0.72423(12) 0.44821(8) 0.0211(2) Uani 1 1 d . . . H10 H 0.1570 0.7529 0.5150 0.025 Uiso 1 1 calc R . . C6 C 0.16508(15) 0.71545(13) -0.02629(8) 0.0244(2) Uani 1 1 d . . . H6 H 0.1630 0.6503 -0.0779 0.029 Uiso 1 1 calc R . . C5 C 0.00493(15) 0.73777(14) -0.03640(8) 0.0261(2) Uani 1 1 d . . . H5 H -0.1034 0.6895 -0.0935 0.031 Uiso 1 1 calc R . . C16 C 0.48965(15) 1.44484(11) 0.25823(8) 0.01981(19) Uani 1 1 d . . . H16 H 0.4876 1.5200 0.2997 0.024 Uiso 1 1 calc R . . C17 C 0.48052(14) 1.45456(11) 0.15704(8) 0.01891(18) Uani 1 1 d . . . H17 H 0.4734 1.5361 0.1295 0.023 Uiso 1 1 calc R . . C7 C 0.50183(12) 0.93263(9) 0.21412(7) 0.01159(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01418(10) 0.01427(10) 0.01597(10) 0.00452(8) 0.00467(8) 0.00807(8) S3 0.01236(10) 0.01914(11) 0.01350(10) 0.00113(8) 0.00460(8) 0.00636(8) S2 0.01720(11) 0.01268(10) 0.01104(9) 0.00157(7) 0.00475(8) 0.00732(8) N1 0.0155(4) 0.0236(4) 0.0137(3) -0.0023(3) 0.0042(3) 0.0061(3) C21 0.0146(4) 0.0193(4) 0.0172(4) 0.0044(3) 0.0038(3) 0.0066(3) C9 0.0155(4) 0.0191(4) 0.0142(4) 0.0016(3) 0.0032(3) 0.0056(3) C8 0.0140(4) 0.0128(4) 0.0147(4) 0.0032(3) 0.0042(3) 0.0061(3) C2 0.0115(4) 0.0149(4) 0.0124(4) 0.0026(3) 0.0032(3) 0.0048(3) C3 0.0143(4) 0.0191(4) 0.0203(4) 0.0017(3) 0.0039(3) 0.0078(3) C20 0.0110(4) 0.0199(4) 0.0153(4) 0.0029(3) 0.0041(3) 0.0060(3) C19 0.0154(4) 0.0159(4) 0.0152(4) 0.0022(3) 0.0051(3) 0.0067(3) C25 0.0148(4) 0.0221(5) 0.0237(5) 0.0065(4) 0.0053(4) 0.0092(4) C23 0.0128(4) 0.0294(5) 0.0178(4) 0.0030(4) 0.0026(3) 0.0068(4) C18 0.0149(4) 0.0203(4) 0.0181(4) 0.0065(3) 0.0053(3) 0.0071(3) C24 0.0149(4) 0.0293(5) 0.0226(5) 0.0087(4) 0.0032(4) 0.0107(4) C15 0.0201(4) 0.0148(4) 0.0181(4) 0.0025(3) 0.0087(3) 0.0079(3) C11 0.0165(4) 0.0230(5) 0.0225(5) 0.0018(4) 0.0072(4) 0.0056(4) C22 0.0152(4) 0.0216(5) 0.0199(4) 0.0020(4) 0.0043(3) 0.0054(4) C14 0.0121(4) 0.0122(4) 0.0150(4) 0.0028(3) 0.0045(3) 0.0052(3) C12 0.0162(4) 0.0187(4) 0.0199(4) -0.0004(3) 0.0030(3) 0.0037(4) C13 0.0178(4) 0.0148(4) 0.0156(4) 0.0005(3) 0.0037(3) 0.0045(3) C4 0.0131(4) 0.0295(5) 0.0246(5) 0.0031(4) 0.0019(4) 0.0081(4) C10 0.0193(5) 0.0252(5) 0.0167(4) 0.0008(4) 0.0065(4) 0.0063(4) C6 0.0176(5) 0.0325(6) 0.0157(4) -0.0057(4) 0.0038(4) 0.0043(4) C5 0.0141(4) 0.0373(6) 0.0174(4) -0.0013(4) 0.0007(4) 0.0039(4) C16 0.0230(5) 0.0148(4) 0.0253(5) 0.0033(4) 0.0104(4) 0.0096(4) C17 0.0168(4) 0.0161(4) 0.0257(5) 0.0080(4) 0.0074(4) 0.0077(3) C7 0.0128(4) 0.0120(4) 0.0114(3) 0.0018(3) 0.0041(3) 0.0064(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.7792(10) . ? S1 C7 1.8496(9) . ? S3 C20 1.7815(10) . ? S3 C7 1.8566(9) . ? S2 C14 1.7727(9) . ? S2 C7 1.8031(9) . ? N1 C6 1.3376(13) . ? N1 C2 1.3390(12) . ? C21 C22 1.3926(14) . ? C21 C20 1.3977(14) . ? C21 H21 0.9500 . ? C9 C10 1.3930(14) . ? C9 C8 1.3968(13) . ? C9 H9 0.9500 . ? C8 C13 1.4006(13) . ? C2 C3 1.3942(13) . ? C2 C7 1.5215(12) . ? C3 C4 1.3914(14) . ? C3 H3 0.9500 . ? C20 C25 1.3964(14) . ? C19 C14 1.3965(13) . ? C19 C18 1.3972(14) . ? C19 H19 0.9500 . ? C25 C24 1.3951(15) . ? C25 H25 0.9500 . ? C23 C24 1.3874(16) . ? C23 C22 1.3918(15) . ? C23 H23 0.9500 . ? C18 C17 1.3911(15) . ? C18 H18 0.9500 . ? C24 H24 0.9500 . ? C15 C16 1.3870(14) . ? C15 C14 1.4013(13) . ? C15 H15 0.9500 . ? C11 C10 1.3918(14) . ? C11 C12 1.3925(15) . ? C11 H11 0.9500 . ? C22 H22 0.9500 . ? C12 C13 1.3914(15) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C4 C5 1.3844(17) . ? C4 H4 0.9500 . ? C10 H10 0.9500 . ? C6 C5 1.3876(16) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C16 C17 1.3926(15) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 S1 C7 104.27(4) . . ? C20 S3 C7 102.10(4) . . ? C14 S2 C7 108.29(4) . . ? C6 N1 C2 117.42(9) . . ? C22 C21 C20 120.08(9) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C10 C9 C8 120.08(9) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C8 C13 119.79(9) . . ? C9 C8 S1 119.68(7) . . ? C13 C8 S1 120.43(7) . . ? N1 C2 C3 123.09(9) . . ? N1 C2 C7 114.21(8) . . ? C3 C2 C7 122.57(8) . . ? C4 C3 C2 118.40(10) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C25 C20 C21 119.87(9) . . ? C25 C20 S3 120.03(8) . . ? C21 C20 S3 120.07(7) . . ? C14 C19 C18 119.40(9) . . ? C14 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C24 C25 C20 119.73(10) . . ? C24 C25 H25 120.1 . . ? C20 C25 H25 120.1 . . ? C24 C23 C22 120.34(10) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C17 C18 C19 120.98(9) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C23 C24 C25 120.16(10) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C16 C15 C14 120.05(9) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C10 C11 C12 120.07(10) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C23 C22 C21 119.79(10) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C19 C14 C15 119.75(9) . . ? C19 C14 S2 126.81(7) . . ? C15 C14 S2 113.44(7) . . ? C13 C12 C11 120.25(9) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 119.79(9) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C5 C4 C3 119.04(10) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C11 C10 C9 120.00(9) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? N1 C6 C5 123.82(10) . . ? N1 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? C4 C5 C6 118.23(10) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C15 C16 C17 120.66(9) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 119.15(9) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C2 C7 S2 115.52(6) . . ? C2 C7 S1 109.67(6) . . ? S2 C7 S1 103.35(4) . . ? C2 C7 S3 107.86(6) . . ? S2 C7 S3 115.25(5) . . ? S1 C7 S3 104.44(4) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C9 C8 C13 -0.10(15) . . . . ? C10 C9 C8 S1 -176.49(8) . . . . ? C7 S1 C8 C9 -103.68(8) . . . . ? C7 S1 C8 C13 79.96(8) . . . . ? C6 N1 C2 C3 -0.11(15) . . . . ? C6 N1 C2 C7 175.88(9) . . . . ? N1 C2 C3 C4 -0.13(16) . . . . ? C7 C2 C3 C4 -175.79(9) . . . . ? C22 C21 C20 C25 -1.12(15) . . . . ? C22 C21 C20 S3 -179.36(8) . . . . ? C7 S3 C20 C25 90.97(9) . . . . ? C7 S3 C20 C21 -90.79(8) . . . . ? C21 C20 C25 C24 1.87(15) . . . . ? S3 C20 C25 C24 -179.89(8) . . . . ? C14 C19 C18 C17 -0.30(15) . . . . ? C22 C23 C24 C25 -0.34(17) . . . . ? C20 C25 C24 C23 -1.14(16) . . . . ? C24 C23 C22 C21 1.09(16) . . . . ? C20 C21 C22 C23 -0.36(15) . . . . ? C18 C19 C14 C15 0.18(14) . . . . ? C18 C19 C14 S2 -178.88(7) . . . . ? C16 C15 C14 C19 0.29(15) . . . . ? C16 C15 C14 S2 179.48(8) . . . . ? C7 S2 C14 C19 -5.43(10) . . . . ? C7 S2 C14 C15 175.45(7) . . . . ? C10 C11 C12 C13 0.72(17) . . . . ? C11 C12 C13 C8 -1.71(16) . . . . ? C9 C8 C13 C12 1.40(15) . . . . ? S1 C8 C13 C12 177.76(8) . . . . ? C2 C3 C4 C5 0.18(16) . . . . ? C12 C11 C10 C9 0.58(17) . . . . ? C8 C9 C10 C11 -0.88(16) . . . . ? C2 N1 C6 C5 0.32(17) . . . . ? C3 C4 C5 C6 0.00(18) . . . . ? N1 C6 C5 C4 -0.26(19) . . . . ? C14 C15 C16 C17 -0.67(16) . . . . ? C19 C18 C17 C16 -0.07(15) . . . . ? C15 C16 C17 C18 0.55(16) . . . . ? N1 C2 C7 S2 171.60(7) . . . . ? C3 C2 C7 S2 -12.38(12) . . . . ? N1 C2 C7 S1 -72.14(9) . . . . ? C3 C2 C7 S1 103.88(9) . . . . ? N1 C2 C7 S3 41.02(10) . . . . ? C3 C2 C7 S3 -142.96(8) . . . . ? C14 S2 C7 C2 -59.35(8) . . . . ? C14 S2 C7 S1 -179.14(4) . . . . ? C14 S2 C7 S3 67.58(6) . . . . ? C8 S1 C7 C2 -55.05(7) . . . . ? C8 S1 C7 S2 68.67(5) . . . . ? C8 S1 C7 S3 -170.41(4) . . . . ? C20 S3 C7 C2 169.76(6) . . . . ? C20 S3 C7 S2 39.03(6) . . . . ? C20 S3 C7 S1 -73.62(5) . . . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.432 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.053