Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Muthalagu, Vetrichelvan' 'Lai, Yee-Hing' 'Mok, K-F.' _publ_contact_author_name 'Mr Vetrichelvan Muthalagu' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Drive 3 117543 SINGAPORE ; _publ_contact_author_email 'SCIP8262@NUS.EDU.SG' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; A novel NS4 quinquedentate macrocyclic ligand: synthesis, structure and properties of Ni(II), Pd(II), Pt(II), Cu(II), Cu(I) and Ag(I) metal complexes of [2,5,14,17]tetrathia[6](1,2)- benzeno[6](2,6)pyridinophane ; data_kf16r _database_code_CSD 188671 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H23 Ag F6 N P S4' _chemical_formula_weight 646.46 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' 'Ag' 'Ag' -0.8971 1.1015 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2538(3) _cell_length_b 12.0217(4) _cell_length_c 12.5274(4) _cell_angle_alpha 106.837(1) _cell_angle_beta 108.836(1) _cell_angle_gamma 102.033(1) _cell_volume 1190.23(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic fragment in capillary' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.804 _exptl_crystal_density_method ? _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.321 _exptl_absorpt_correction_type 'Sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.591 _exptl_absorpt_correction_T_max 0.935 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9822 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4804 _reflns_number_observed 3758 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.8104P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4803 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_obs 0.0363 _refine_ls_wR_factor_all 0.1037 _refine_ls_wR_factor_obs 0.0863 _refine_ls_goodness_of_fit_all 1.013 _refine_ls_goodness_of_fit_obs 1.061 _refine_ls_restrained_S_all 1.119 _refine_ls_restrained_S_obs 1.061 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ag Ag 0.44774(3) 0.20760(3) 0.47931(3) 0.05033(11) Uani 1 d . . C1 C 0.3991(5) 0.3366(4) 0.7407(3) 0.0538(10) Uani 1 d . . H1A H 0.3709(5) 0.4046(4) 0.7828(3) 0.065 Uiso 1 calc R . H1B H 0.3881(5) 0.2770(4) 0.7783(3) 0.065 Uiso 1 calc R . S2 S 0.25245(11) 0.26513(9) 0.58444(9) 0.0445(2) Uani 1 d . . C3 C 0.2404(5) 0.3964(3) 0.5430(3) 0.0472(9) Uani 1 d . . H3A H 0.1701(5) 0.4329(3) 0.5732(3) 0.057 Uiso 1 calc R . H3B H 0.3472(5) 0.4581(3) 0.5803(3) 0.057 Uiso 1 calc R . C4 C 0.1743(5) 0.3561(4) 0.4048(3) 0.0467(9) Uani 1 d . . H4A H 0.1374(5) 0.4191(4) 0.3820(3) 0.056 Uiso 1 calc R . H4B H 0.0822(5) 0.2807(4) 0.3668(3) 0.056 Uiso 1 calc R . S5 S 0.32756(11) 0.33047(8) 0.34913(8) 0.0427(2) Uani 1 d . . C6 C 0.2050(5) 0.2223(3) 0.1911(3) 0.0460(9) Uani 1 d . . H6A H 0.1292(5) 0.2579(3) 0.1519(3) 0.055 Uiso 1 calc R . H6B H 0.2760(5) 0.2143(3) 0.1489(3) 0.055 Uiso 1 calc R . C7 C 0.1111(4) 0.0955(3) 0.1734(3) 0.0404(8) Uani 1 d . . C8 C -0.0528(5) 0.0692(4) 0.1480(3) 0.0495(9) Uani 1 d . . H8A H -0.0987(5) 0.1307(4) 0.1450(3) 0.059 Uiso 1 calc R . C9 C -0.1496(5) -0.0466(4) 0.1269(4) 0.0588(11) Uani 1 d . . H9A H -0.2588(5) -0.0622(4) 0.1107(4) 0.071 Uiso 1 calc R . C10 C -0.0830(5) -0.1378(4) 0.1300(4) 0.0583(11) Uani 1 d . . H10A H -0.1469(5) -0.2153(4) 0.1171(4) 0.070 Uiso 1 calc R . C11 C 0.0779(5) -0.1152(3) 0.1522(3) 0.0488(9) Uani 1 d . . H11A H 0.1211(5) -0.1785(3) 0.1525(3) 0.059 Uiso 1 calc R . C12 C 0.1782(4) 0.0010(3) 0.1742(3) 0.0389(8) Uani 1 d . . C13 C 0.3530(4) 0.0177(3) 0.1986(3) 0.0434(8) Uani 1 d . . H13A H 0.4064(4) 0.0971(3) 0.2002(3) 0.052 Uiso 1 calc R . H13B H 0.3615(4) -0.0465(3) 0.1353(3) 0.052 Uiso 1 calc R . S14 S 0.44602(11) 0.00844(8) 0.34692(8) 0.0409(2) Uani 1 d . . C15 C 0.6540(5) 0.0279(4) 0.3685(4) 0.0519(10) Uani 1 d . . H15A H 0.7079(5) 0.0168(4) 0.4432(4) 0.062 Uiso 1 calc R . H15B H 0.6533(5) -0.0383(4) 0.3018(4) 0.062 Uiso 1 calc R . C16 C 0.7569(5) 0.1484(4) 0.3759(4) 0.0527(10) Uani 1 d . . H16A H 0.7185(5) 0.1501(4) 0.2948(4) 0.063 Uiso 1 calc R . H16B H 0.8670(5) 0.1475(4) 0.3971(4) 0.063 Uiso 1 calc R . S17 S 0.76366(12) 0.29050(9) 0.48117(9) 0.0488(2) Uani 1 d . . C18 C 0.8402(5) 0.2765(4) 0.6284(4) 0.0527(10) Uani 1 d . . H18A H 0.7987(5) 0.1913(4) 0.6180(4) 0.063 Uiso 1 calc R . H18B H 0.9575(5) 0.3018(4) 0.6617(4) 0.063 Uiso 1 calc R . C19 C 0.7886(4) 0.3557(4) 0.7144(3) 0.0456(9) Uani 1 d . . C20 C 0.8975(5) 0.4577(4) 0.8170(4) 0.0591(11) Uani 1 d . . H20A H 1.0076(5) 0.4807(4) 0.8344(4) 0.071 Uiso 1 calc R . C21 C 0.8404(6) 0.5248(4) 0.8929(4) 0.0636(12) Uani 1 d . . H21A H 0.9120(6) 0.5944(4) 0.9617(4) 0.076 Uiso 1 calc R . C22 C 0.6795(6) 0.4895(4) 0.8677(3) 0.0562(11) Uani 1 d . . H22A H 0.6403(6) 0.5343(4) 0.9188(3) 0.067 Uiso 1 calc R . C23 C 0.5745(5) 0.3851(3) 0.7640(3) 0.0429(8) Uani 1 d . . N24 N 0.6289(3) 0.3213(3) 0.6879(3) 0.0401(7) Uani 1 d . . P P 0.34860(12) 0.70038(9) 0.90479(9) 0.0441(2) Uani 1 d . . F1 F 0.3988(4) 0.8418(2) 0.9251(3) 0.0793(8) Uani 1 d . . F2 F 0.2966(3) 0.5588(2) 0.8845(3) 0.0789(8) Uani 1 d . . F3 F 0.2554(5) 0.7209(3) 0.9877(4) 0.1235(15) Uani 1 d . . F4 F 0.4330(5) 0.6759(3) 0.8141(4) 0.1182(13) Uani 1 d . . F5 F 0.5077(4) 0.7235(4) 1.0114(4) 0.150(2) Uani 1 d . . F6 F 0.1880(4) 0.6739(3) 0.7935(3) 0.1126(13) Uani 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 Ag 0.0427(2) 0.0571(2) 0.0401(2) 0.00396(13) 0.01233(12) 0.02351(14) C1 0.067(3) 0.063(3) 0.042(2) 0.019(2) 0.031(2) 0.034(2) S2 0.0430(5) 0.0437(5) 0.0491(5) 0.0161(4) 0.0229(4) 0.0150(4) C3 0.050(2) 0.041(2) 0.049(2) 0.011(2) 0.021(2) 0.019(2) C4 0.047(2) 0.046(2) 0.048(2) 0.017(2) 0.018(2) 0.021(2) S5 0.0420(5) 0.0377(5) 0.0438(5) 0.0144(4) 0.0159(4) 0.0091(4) C6 0.056(2) 0.044(2) 0.036(2) 0.016(2) 0.015(2) 0.017(2) C7 0.045(2) 0.042(2) 0.028(2) 0.0097(14) 0.0121(14) 0.011(2) C8 0.045(2) 0.053(2) 0.041(2) 0.008(2) 0.014(2) 0.018(2) C9 0.041(2) 0.068(3) 0.047(2) 0.004(2) 0.018(2) 0.004(2) C10 0.059(3) 0.047(2) 0.048(2) 0.008(2) 0.021(2) -0.006(2) C11 0.059(2) 0.036(2) 0.040(2) 0.007(2) 0.019(2) 0.010(2) C12 0.044(2) 0.036(2) 0.029(2) 0.0052(14) 0.0145(14) 0.0093(15) C13 0.052(2) 0.044(2) 0.036(2) 0.014(2) 0.022(2) 0.018(2) S14 0.0450(5) 0.0381(5) 0.0437(5) 0.0167(4) 0.0213(4) 0.0157(4) C15 0.053(2) 0.058(2) 0.060(2) 0.025(2) 0.031(2) 0.033(2) C16 0.045(2) 0.066(3) 0.061(2) 0.028(2) 0.032(2) 0.025(2) S17 0.0452(5) 0.0532(6) 0.0521(6) 0.0261(5) 0.0215(4) 0.0137(4) C18 0.036(2) 0.074(3) 0.054(2) 0.031(2) 0.019(2) 0.021(2) C19 0.039(2) 0.051(2) 0.043(2) 0.025(2) 0.009(2) 0.011(2) C20 0.046(2) 0.056(3) 0.055(3) 0.028(2) 0.000(2) 0.000(2) C21 0.076(3) 0.039(2) 0.043(2) 0.013(2) -0.004(2) 0.004(2) C22 0.082(3) 0.043(2) 0.034(2) 0.013(2) 0.011(2) 0.026(2) C23 0.059(2) 0.040(2) 0.031(2) 0.017(2) 0.015(2) 0.021(2) N24 0.039(2) 0.041(2) 0.035(2) 0.0138(13) 0.0118(13) 0.0111(13) P 0.0413(5) 0.0456(5) 0.0506(6) 0.0213(4) 0.0219(4) 0.0158(4) F1 0.090(2) 0.0486(15) 0.100(2) 0.0326(15) 0.042(2) 0.0138(14) F2 0.086(2) 0.0512(14) 0.127(2) 0.041(2) 0.063(2) 0.0346(14) F3 0.199(4) 0.071(2) 0.165(3) 0.039(2) 0.155(3) 0.048(2) F4 0.145(3) 0.112(3) 0.159(3) 0.059(3) 0.125(3) 0.050(2) F5 0.086(2) 0.142(3) 0.145(3) 0.090(3) -0.043(2) -0.016(2) F6 0.072(2) 0.105(3) 0.119(3) 0.058(2) -0.011(2) 0.008(2) _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 Ag N24 2.378(3) . ? Ag S14 2.4798(9) . ? Ag S5 2.6435(10) . ? Ag S2 2.6475(9) . ? Ag S17 2.8754(10) . ? C1 C23 1.504(6) . ? C1 S2 1.799(4) . ? S2 C3 1.812(4) . ? C3 C4 1.521(5) . ? C4 S5 1.813(4) . ? S5 C6 1.828(4) . ? C6 C7 1.503(5) . ? C7 C8 1.390(5) . ? C7 C12 1.404(5) . ? C8 C9 1.387(6) . ? C9 C10 1.369(6) . ? C10 C11 1.374(6) . ? C11 C12 1.400(5) . ? C12 C13 1.504(5) . ? C13 S14 1.826(4) . ? S14 C15 1.809(4) . ? C15 C16 1.518(6) . ? C16 S17 1.805(4) . ? S17 C18 1.821(4) . ? C18 C19 1.491(6) . ? C19 N24 1.347(5) . ? C19 C20 1.381(5) . ? C20 C21 1.376(7) . ? C21 C22 1.361(7) . ? C22 C23 1.392(5) . ? C23 N24 1.340(5) . ? P F5 1.540(3) . ? P F3 1.550(3) . ? P F4 1.569(3) . ? P F6 1.569(3) . ? P F1 1.586(3) . ? P F2 1.588(3) . ? 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 N24 Ag S14 125.36(7) . . ? N24 Ag S5 118.06(7) . . ? S14 Ag S5 111.38(3) . . ? N24 Ag S2 77.16(7) . . ? S14 Ag S2 132.39(3) . . ? S5 Ag S2 82.73(3) . . ? N24 Ag S17 73.87(7) . . ? S14 Ag S17 81.52(3) . . ? S5 Ag S17 93.60(3) . . ? S2 Ag S17 144.84(3) . . ? C23 C1 S2 117.8(3) . . ? C1 S2 C3 102.5(2) . . ? C1 S2 Ag 98.39(13) . . ? C3 S2 Ag 95.59(13) . . ? C4 C3 S2 110.1(3) . . ? C3 C4 S5 111.2(3) . . ? C4 S5 C6 102.1(2) . . ? C4 S5 Ag 99.06(13) . . ? C6 S5 Ag 108.62(12) . . ? C7 C6 S5 116.3(2) . . ? C8 C7 C12 118.8(3) . . ? C8 C7 C6 117.8(3) . . ? C12 C7 C6 123.4(3) . . ? C9 C8 C7 121.6(4) . . ? C10 C9 C8 119.5(4) . . ? C9 C10 C11 120.2(4) . . ? C10 C11 C12 121.3(4) . . ? C11 C12 C7 118.6(3) . . ? C11 C12 C13 117.7(3) . . ? C7 C12 C13 123.7(3) . . ? C12 C13 S14 106.6(2) . . ? C15 S14 C13 103.8(2) . . ? C15 S14 Ag 106.23(14) . . ? C13 S14 Ag 98.84(12) . . ? C16 C15 S14 118.5(3) . . ? C15 C16 S17 118.1(3) . . ? C16 S17 C18 103.2(2) . . ? C16 S17 Ag 98.59(13) . . ? C18 S17 Ag 85.89(13) . . ? C19 C18 S17 109.6(3) . . ? N24 C19 C20 121.3(4) . . ? N24 C19 C18 116.3(3) . . ? C20 C19 C18 122.4(4) . . ? C21 C20 C19 118.8(4) . . ? C22 C21 C20 120.2(4) . . ? C21 C22 C23 118.9(4) . . ? N24 C23 C22 121.1(4) . . ? N24 C23 C1 118.7(3) . . ? C22 C23 C1 120.0(4) . . ? C23 N24 C19 119.6(3) . . ? C23 N24 Ag 118.5(2) . . ? C19 N24 Ag 117.4(2) . . ? F5 P F3 93.4(3) . . ? F5 P F4 89.9(3) . . ? F3 P F4 176.6(3) . . ? F5 P F6 178.2(3) . . ? F3 P F6 88.1(3) . . ? F4 P F6 88.6(2) . . ? F5 P F1 91.2(2) . . ? F3 P F1 91.1(2) . . ? F4 P F1 89.7(2) . . ? F6 P F1 89.7(2) . . ? F5 P F2 89.1(2) . . ? F3 P F2 88.4(2) . . ? F4 P F2 90.8(2) . . ? F6 P F2 90.0(2) . . ? F1 P F2 179.4(2) . . ? _refine_diff_density_max 0.802 _refine_diff_density_min -1.031 _refine_diff_density_rms 0.076 data_kf13 _database_code_CSD 188672 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 F12 N O P2 Pd S4' _chemical_formula_weight 807.98 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.09930(10) _cell_length_b 20.102 _cell_length_c 17.3608(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.5260(10) _cell_angle_gamma 90.00 _cell_volume 2825.52(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.899 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 1.163 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15952 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5721 _reflns_number_gt 3856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0596P)^2^+8.3481P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5721 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _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 Pd Pd 0.16204(6) 0.17782(2) 0.25239(3) 0.04752(17) Uani 1 1 d . . . C1 C 0.4541(12) 0.2635(4) 0.2890(5) 0.095(3) Uani 1 1 d . . . H1A H 0.5174 0.3044 0.2908 0.114 Uiso 1 1 calc R . . H1B H 0.4836 0.2374 0.3343 0.114 Uiso 1 1 calc R . . S2 S 0.2336(3) 0.28231(9) 0.28792(11) 0.0798(7) Uani 1 1 d . . . C3 C 0.1606(16) 0.2815(4) 0.3869(5) 0.100(3) Uani 1 1 d . . . H3A H 0.2210 0.2489 0.4178 0.120 Uiso 1 1 calc R . . H3B H 0.1744 0.3249 0.4106 0.120 Uiso 1 1 calc R . . C4 C -0.0190(15) 0.2633(4) 0.3800(5) 0.098(3) Uani 1 1 d . . . H4A H -0.0764 0.2968 0.3492 0.117 Uiso 1 1 calc R . . H4B H -0.0655 0.2637 0.4309 0.117 Uiso 1 1 calc R . . S5 S -0.0552(2) 0.18158(9) 0.33604(10) 0.0622(5) Uani 1 1 d . . . C6 C 0.0007(8) 0.1300(3) 0.4193(3) 0.0549(17) Uani 1 1 d . . . H6A H 0.1152 0.1382 0.4341 0.066 Uiso 1 1 calc R . . H6B H -0.0670 0.1425 0.4622 0.066 Uiso 1 1 calc R . . C7 C -0.0220(7) 0.0575(3) 0.4030(3) 0.0454(14) Uani 1 1 d . . . C8 C -0.1804(8) 0.0337(4) 0.3854(4) 0.0624(19) Uani 1 1 d . . . H8A H -0.2676 0.0637 0.3811 0.075 Uiso 1 1 calc R . . C9 C -0.2107(10) -0.0325(5) 0.3742(4) 0.074(2) Uani 1 1 d . . . H9A H -0.3171 -0.0471 0.3618 0.088 Uiso 1 1 calc R . . C10 C -0.0837(10) -0.0773(4) 0.3814(4) 0.0644(19) Uani 1 1 d . . . H10A H -0.1040 -0.1225 0.3747 0.077 Uiso 1 1 calc R . . C11 C 0.0753(8) -0.0552(3) 0.3985(3) 0.0540(16) Uani 1 1 d . . . H11A H 0.1609 -0.0859 0.4034 0.065 Uiso 1 1 calc R . . C12 C 0.1083(7) 0.0119(3) 0.4086(3) 0.0451(14) Uani 1 1 d . . . C13 C 0.2840(7) 0.0335(3) 0.4228(3) 0.0467(14) Uani 1 1 d . . . H13A H 0.3510 -0.0055 0.4338 0.056 Uiso 1 1 calc R . . H13B H 0.2889 0.0617 0.4682 0.056 Uiso 1 1 calc R . . S14 S 0.37287(18) 0.07852(8) 0.34274(9) 0.0498(4) Uani 1 1 d . . . C15 C 0.3526(9) 0.0186(4) 0.2652(4) 0.0605(18) Uani 1 1 d . . . H15A H 0.4324 0.0301 0.2267 0.073 Uiso 1 1 calc R . . H15B H 0.3837 -0.0246 0.2858 0.073 Uiso 1 1 calc R . . C16 C 0.1854(9) 0.0115(3) 0.2248(4) 0.0595(18) Uani 1 1 d . . . H16A H 0.1074 -0.0038 0.2623 0.071 Uiso 1 1 calc R . . H16B H 0.1941 -0.0232 0.1862 0.071 Uiso 1 1 calc R . . S17 S 0.09968(19) 0.08430(8) 0.17827(8) 0.0498(4) Uani 1 1 d . . . C18 C 0.2484(9) 0.1012(4) 0.1042(3) 0.0594(18) Uani 1 1 d . . . H18A H 0.2895 0.0591 0.0852 0.071 Uiso 1 1 calc R . . H18B H 0.1917 0.1233 0.0615 0.071 Uiso 1 1 calc R . . C19 C 0.3919(9) 0.1427(4) 0.1293(4) 0.0584(17) Uani 1 1 d . . . C20 C 0.5392(10) 0.1440(5) 0.0915(5) 0.081(2) Uani 1 1 d . . . H20A H 0.5551 0.1157 0.0499 0.097 Uiso 1 1 calc R . . C21 C 0.6613(12) 0.1863(5) 0.1144(7) 0.098(3) Uani 1 1 d . . . H21A H 0.7600 0.1876 0.0883 0.117 Uiso 1 1 calc R . . C22 C 0.6376(11) 0.2277(5) 0.1774(6) 0.096(3) Uani 1 1 d . . . H22A H 0.7199 0.2574 0.1929 0.115 Uiso 1 1 calc R . . C23 C 0.4930(10) 0.2247(4) 0.2165(4) 0.074(2) Uani 1 1 d . . . N24 N 0.3704(7) 0.1820(3) 0.1908(3) 0.0552(14) Uani 1 1 d . . . P1 P 0.2812(3) 0.05758(9) 0.87171(10) 0.0617(5) Uani 1 1 d . . . F1 F 0.4390(10) 0.0290(6) 0.9079(6) 0.225(5) Uani 1 1 d . . . F2 F 0.1781(10) 0.0210(3) 0.9326(3) 0.152(3) Uani 1 1 d . . . F3 F 0.1216(10) 0.0836(4) 0.8336(5) 0.187(4) Uani 1 1 d . . . F4 F 0.3839(10) 0.0947(3) 0.8112(4) 0.168(4) Uani 1 1 d . . . F5 F 0.2714(7) -0.0038(2) 0.8164(3) 0.1018(17) Uani 1 1 d . . . F6 F 0.2908(9) 0.1189(3) 0.9276(3) 0.142(3) Uani 1 1 d . . . P2 P 0.0552(2) 0.29964(9) 0.04258(10) 0.0555(4) Uani 1 1 d . . . F7 F 0.0150(11) 0.3142(7) 0.1229(4) 0.258(7) Uani 1 1 d . . . F8 F 0.0270(7) 0.2277(3) 0.0598(8) 0.239(6) Uani 1 1 d . . . F9 F 0.0982(10) 0.2860(7) -0.0395(4) 0.225(5) Uani 1 1 d . . . F10 F 0.0817(8) 0.3724(3) 0.0276(7) 0.201(5) Uani 1 1 d . . . F11 F -0.1338(5) 0.3088(2) 0.0186(3) 0.0932(15) Uani 1 1 d . . . F12 F 0.2448(5) 0.2902(3) 0.0666(3) 0.1001(16) Uani 1 1 d . . . O1 O 0.1609(14) -0.0847(6) 1.0368(7) 0.209(5) Uiso 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 Pd 0.0591(3) 0.0461(3) 0.0372(2) 0.0017(2) -0.0010(2) 0.0014(2) C1 0.111(7) 0.080(6) 0.091(6) 0.013(5) -0.036(5) -0.037(5) S2 0.134(2) 0.0445(10) 0.0596(11) 0.0044(8) -0.0200(12) -0.0016(11) C3 0.194(12) 0.045(5) 0.059(5) -0.013(4) -0.009(6) 0.009(6) C4 0.161(10) 0.065(5) 0.067(5) -0.004(4) 0.012(6) 0.044(6) S5 0.0705(11) 0.0686(11) 0.0478(9) 0.0077(8) 0.0076(8) 0.0340(9) C6 0.056(4) 0.073(5) 0.036(3) 0.006(3) 0.008(3) 0.022(3) C7 0.040(3) 0.062(4) 0.034(3) 0.007(3) 0.007(2) 0.006(3) C8 0.044(4) 0.094(6) 0.049(4) 0.012(4) 0.006(3) 0.013(4) C9 0.060(5) 0.104(7) 0.057(4) 0.007(4) -0.003(4) -0.019(5) C10 0.083(5) 0.062(4) 0.048(4) 0.003(3) 0.003(4) -0.020(4) C11 0.058(4) 0.060(4) 0.045(3) 0.013(3) 0.005(3) 0.006(3) C12 0.043(3) 0.059(4) 0.033(3) 0.008(3) 0.002(2) 0.004(3) C13 0.044(3) 0.056(4) 0.040(3) 0.006(3) -0.004(3) 0.013(3) S14 0.0377(8) 0.0620(10) 0.0498(8) 0.0055(7) 0.0006(7) 0.0014(7) C15 0.066(4) 0.065(4) 0.051(4) 0.002(3) 0.019(3) 0.020(3) C16 0.087(5) 0.045(4) 0.047(3) -0.001(3) 0.007(3) -0.006(3) S17 0.0502(9) 0.0595(10) 0.0396(8) -0.0025(7) 0.0013(7) -0.0085(7) C18 0.069(5) 0.071(5) 0.039(3) 0.004(3) 0.013(3) -0.004(4) C19 0.065(4) 0.068(4) 0.042(3) 0.016(3) 0.010(3) -0.004(4) C20 0.070(5) 0.097(6) 0.076(5) 0.034(5) 0.024(4) 0.000(5) C21 0.070(6) 0.111(8) 0.113(8) 0.046(7) 0.020(6) -0.008(6) C22 0.073(6) 0.106(7) 0.106(7) 0.053(6) -0.022(5) -0.043(5) C23 0.077(5) 0.077(5) 0.066(5) 0.026(4) -0.018(4) -0.023(4) N24 0.054(3) 0.054(3) 0.057(3) 0.020(3) -0.006(3) -0.013(3) P1 0.0785(13) 0.0577(11) 0.0496(9) -0.0059(8) 0.0158(9) -0.0159(9) F1 0.142(7) 0.301(12) 0.226(10) -0.068(9) -0.095(7) 0.060(7) F2 0.246(8) 0.115(5) 0.097(4) -0.018(3) 0.086(5) -0.082(5) F3 0.181(7) 0.191(8) 0.186(8) -0.017(6) -0.044(6) 0.096(6) F4 0.275(9) 0.115(5) 0.121(5) -0.051(4) 0.119(5) -0.114(5) F5 0.120(4) 0.086(3) 0.101(4) -0.037(3) 0.028(3) -0.029(3) F6 0.252(7) 0.090(4) 0.089(3) -0.041(3) 0.086(4) -0.080(4) P2 0.0510(10) 0.0572(10) 0.0581(10) 0.0126(8) -0.0022(8) -0.0048(8) F7 0.171(8) 0.53(2) 0.070(4) -0.036(7) -0.019(4) 0.151(10) F8 0.068(4) 0.094(5) 0.56(2) 0.119(8) 0.008(7) -0.007(3) F9 0.131(6) 0.448(17) 0.097(5) -0.074(8) -0.009(4) 0.049(8) F10 0.108(5) 0.087(4) 0.402(14) 0.073(6) -0.113(7) -0.037(4) F11 0.057(3) 0.091(3) 0.131(4) 0.016(3) -0.022(3) -0.003(2) F12 0.053(3) 0.104(4) 0.142(5) 0.035(3) -0.016(3) -0.001(2) _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 Pd N24 2.024(6) . ? Pd S2 2.2603(19) . ? Pd S5 2.3123(18) . ? Pd S17 2.3259(16) . ? C1 C23 1.522(12) . ? C1 S2 1.825(10) . ? S2 C3 1.832(9) . ? C3 C4 1.502(14) . ? C4 S5 1.832(9) . ? S5 C6 1.826(6) . ? C6 C7 1.496(9) . ? C7 C8 1.395(9) . ? C7 C12 1.398(8) . ? C8 C9 1.366(11) . ? C9 C10 1.371(11) . ? C10 C11 1.387(9) . ? C11 C12 1.385(9) . ? C12 C13 1.502(8) . ? C13 S14 1.823(6) . ? S14 C15 1.810(7) . ? C15 C16 1.516(9) . ? C16 S17 1.802(7) . ? S17 C18 1.818(6) . ? C18 C19 1.487(9) . ? C19 N24 1.342(9) . ? C19 C20 1.377(10) . ? C20 C21 1.355(13) . ? C21 C22 1.390(13) . ? C22 C23 1.371(12) . ? C23 N24 1.378(9) . ? P1 F1 1.522(8) . ? P1 F3 1.529(7) . ? P1 F2 1.549(5) . ? P1 F4 1.550(5) . ? P1 F5 1.563(5) . ? P1 F6 1.570(5) . ? P2 F7 1.471(7) . ? P2 F8 1.496(6) . ? P2 F10 1.501(6) . ? P2 F9 1.501(7) . ? P2 F11 1.586(5) . ? P2 F12 1.591(5) . ? 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 N24 Pd S2 83.95(17) . . ? N24 Pd S5 171.84(16) . . ? S2 Pd S5 89.54(8) . . ? N24 Pd S17 84.99(16) . . ? S2 Pd S17 162.23(7) . . ? S5 Pd S17 102.49(7) . . ? C23 C1 S2 108.8(5) . . ? C1 S2 C3 109.2(5) . . ? C1 S2 Pd 93.1(3) . . ? C3 S2 Pd 99.3(3) . . ? C4 C3 S2 105.2(6) . . ? C3 C4 S5 113.3(6) . . ? C6 S5 C4 98.4(4) . . ? C6 S5 Pd 107.6(2) . . ? C4 S5 Pd 100.1(4) . . ? C7 C6 S5 112.2(4) . . ? C8 C7 C12 118.6(6) . . ? C8 C7 C6 118.9(6) . . ? C12 C7 C6 122.4(6) . . ? C9 C8 C7 121.7(7) . . ? C8 C9 C10 119.7(7) . . ? C9 C10 C11 119.9(7) . . ? C12 C11 C10 120.9(6) . . ? C11 C12 C7 119.1(6) . . ? C11 C12 C13 118.8(5) . . ? C7 C12 C13 122.1(6) . . ? C12 C13 S14 114.2(4) . . ? C15 S14 C13 102.0(3) . . ? C16 C15 S14 118.0(4) . . ? C15 C16 S17 117.4(5) . . ? C16 S17 C18 102.3(3) . . ? C16 S17 Pd 109.5(2) . . ? C18 S17 Pd 95.9(2) . . ? C19 C18 S17 115.2(4) . . ? N24 C19 C20 120.0(7) . . ? N24 C19 C18 116.5(6) . . ? C20 C19 C18 123.5(7) . . ? C21 C20 C19 120.4(9) . . ? C20 C21 C22 119.5(9) . . ? C23 C22 C21 120.0(8) . . ? C22 C23 N24 119.1(8) . . ? C22 C23 C1 125.8(8) . . ? N24 C23 C1 115.1(7) . . ? C19 N24 C23 121.0(6) . . ? C19 N24 Pd 121.6(4) . . ? C23 N24 Pd 117.3(5) . . ? F1 P1 F3 177.6(5) . . ? F1 P1 F2 90.1(6) . . ? F3 P1 F2 89.6(5) . . ? F1 P1 F4 90.1(6) . . ? F3 P1 F4 90.3(5) . . ? F2 P1 F4 179.5(4) . . ? F1 P1 F5 89.1(4) . . ? F3 P1 F5 88.6(4) . . ? F2 P1 F5 91.4(3) . . ? F4 P1 F5 89.0(3) . . ? F1 P1 F6 90.8(5) . . ? F3 P1 F6 91.5(4) . . ? F2 P1 F6 88.3(3) . . ? F4 P1 F6 91.3(3) . . ? F5 P1 F6 179.7(3) . . ? F7 P2 F8 88.0(7) . . ? F7 P2 F10 90.4(7) . . ? F8 P2 F10 178.3(7) . . ? F7 P2 F9 178.9(8) . . ? F8 P2 F9 93.1(7) . . ? F10 P2 F9 88.6(7) . . ? F7 P2 F11 89.3(4) . . ? F8 P2 F11 90.7(3) . . ? F10 P2 F11 89.0(3) . . ? F9 P2 F11 91.1(4) . . ? F7 P2 F12 90.7(4) . . ? F8 P2 F12 89.1(3) . . ? F10 P2 F12 91.2(3) . . ? F9 P2 F12 88.9(4) . . ? F11 P2 F12 179.8(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.033 _refine_diff_density_min -0.765 _refine_diff_density_rms 0.101 data_kf14 _database_code_CSD 188673 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 F12 N O P2 Pt S4' _chemical_formula_weight 896.67 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' 'Pt' 'Pt' -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.04370(10) _cell_length_b 20.2495(2) _cell_length_c 17.4965(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.3750(10) _cell_angle_gamma 90.00 _cell_volume 2849.03(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 5.427 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16298 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 26.34 _reflns_number_total 5785 _reflns_number_gt 4559 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0429P)^2^+5.2691P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5785 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Pt Pt 0.64721(3) 0.678207(10) -0.248391(11) 0.04277(8) Uani 1 1 d . . . C1 C 0.9379(10) 0.7663(4) -0.2126(5) 0.085(2) Uani 1 1 d . . . H1A H 0.9984 0.8078 -0.2124 0.102 Uiso 1 1 calc R . . H1B H 0.9714 0.7415 -0.1674 0.102 Uiso 1 1 calc R . . S2 S 0.7131(3) 0.78233(8) -0.21204(10) 0.0666(5) Uani 1 1 d . . . C3 C 0.6403(11) 0.7801(3) -0.1143(4) 0.077(2) Uani 1 1 d . . . H3A H 0.7043 0.7486 -0.0839 0.092 Uiso 1 1 calc R . . H3B H 0.6506 0.8233 -0.0906 0.092 Uiso 1 1 calc R . . C4 C 0.4621(11) 0.7596(3) -0.1203(4) 0.079(2) Uani 1 1 d . . . H4A H 0.4007 0.7923 -0.1501 0.095 Uiso 1 1 calc R . . H4B H 0.4165 0.7589 -0.0695 0.095 Uiso 1 1 calc R . . S5 S 0.43187(19) 0.67851(8) -0.16443(9) 0.0522(4) Uani 1 1 d . . . C6 C 0.4960(7) 0.6272(3) -0.0819(3) 0.0487(13) Uani 1 1 d . . . H6A H 0.6116 0.6362 -0.0688 0.058 Uiso 1 1 calc R . . H6B H 0.4300 0.6390 -0.0383 0.058 Uiso 1 1 calc R . . C7 C 0.4754(6) 0.5549(3) -0.0979(3) 0.0415(12) Uani 1 1 d . . . C8 C 0.3167(7) 0.5305(4) -0.1146(3) 0.0581(16) Uani 1 1 d . . . H8A H 0.2276 0.5597 -0.1181 0.070 Uiso 1 1 calc R . . C9 C 0.2887(9) 0.4644(4) -0.1260(4) 0.071(2) Uani 1 1 d . . . H9A H 0.1824 0.4495 -0.1388 0.085 Uiso 1 1 calc R . . C10 C 0.4181(10) 0.4202(3) -0.1183(4) 0.0651(18) Uani 1 1 d . . . H10A H 0.3994 0.3751 -0.1245 0.078 Uiso 1 1 calc R . . C11 C 0.5770(8) 0.4437(3) -0.1012(3) 0.0530(14) Uani 1 1 d . . . H11A H 0.6642 0.4137 -0.0960 0.064 Uiso 1 1 calc R . . C12 C 0.6096(6) 0.5107(3) -0.0915(3) 0.0406(12) Uani 1 1 d . . . C13 C 0.7855(6) 0.5330(3) -0.0774(3) 0.0465(13) Uani 1 1 d . . . H13A H 0.8542 0.4947 -0.0663 0.056 Uiso 1 1 calc R . . H13B H 0.7893 0.5612 -0.0325 0.056 Uiso 1 1 calc R . . S14 S 0.87363(16) 0.57782(8) -0.15713(8) 0.0495(3) Uani 1 1 d . . . C15 C 0.8515(8) 0.5193(3) -0.2346(3) 0.0621(17) Uani 1 1 d . . . H15A H 0.9304 0.5312 -0.2733 0.074 Uiso 1 1 calc R . . H15B H 0.8841 0.4762 -0.2151 0.074 Uiso 1 1 calc R . . C16 C 0.6804(8) 0.5122(3) -0.2739(3) 0.0570(15) Uani 1 1 d . . . H16A H 0.6029 0.4972 -0.2359 0.068 Uiso 1 1 calc R . . H16B H 0.6877 0.4776 -0.3121 0.068 Uiso 1 1 calc R . . S17 S 0.59256(18) 0.58461(8) -0.31989(8) 0.0490(3) Uani 1 1 d . . . C18 C 0.7411(8) 0.6010(3) -0.3945(3) 0.0611(17) Uani 1 1 d . . . H18A H 0.7852 0.5593 -0.4122 0.073 Uiso 1 1 calc R . . H18B H 0.6830 0.6217 -0.4374 0.073 Uiso 1 1 calc R . . C19 C 0.8837(8) 0.6446(3) -0.3693(4) 0.0596(16) Uani 1 1 d . . . C20 C 1.0340(9) 0.6463(4) -0.4058(4) 0.078(2) Uani 1 1 d . . . H20A H 1.0534 0.6180 -0.4465 0.094 Uiso 1 1 calc R . . C21 C 1.1534(10) 0.6895(5) -0.3818(7) 0.102(3) Uani 1 1 d . . . H21A H 1.2541 0.6911 -0.4067 0.123 Uiso 1 1 calc R . . C22 C 1.1270(10) 0.7312(5) -0.3207(6) 0.087(3) Uani 1 1 d . . . H22A H 1.2087 0.7612 -0.3051 0.105 Uiso 1 1 calc R . . C23 C 0.9761(8) 0.7279(3) -0.2827(4) 0.0655(18) Uani 1 1 d . . . N24 N 0.8581(6) 0.6844(2) -0.3089(3) 0.0510(12) Uani 1 1 d . . . P1 P 0.04957(19) 0.69995(8) 0.03726(9) 0.0519(4) Uani 1 1 d . . . F1 F 0.0981(9) 0.7113(5) -0.0469(3) 0.178(3) Uani 1 1 d . . . F2 F 0.0215(6) 0.7750(3) 0.0494(5) 0.169(3) Uani 1 1 d . . . F3 F -0.0004(10) 0.6896(5) 0.1197(3) 0.191(4) Uani 1 1 d . . . F4 F 0.0763(7) 0.6252(3) 0.0261(5) 0.152(3) Uani 1 1 d . . . F5 F 0.2389(5) 0.7097(2) 0.0621(3) 0.0960(15) Uani 1 1 d . . . F6 F -0.1400(5) 0.6904(2) 0.0113(3) 0.0914(14) Uani 1 1 d . . . P2 P 0.2150(2) 0.44319(9) -0.37382(10) 0.0614(4) Uani 1 1 d . . . F7 F 0.3648(11) 0.4121(5) -0.3348(5) 0.210(4) Uani 1 1 d . . . F8 F 0.3283(9) 0.4786(3) -0.4316(3) 0.151(3) Uani 1 1 d . . . F9 F 0.0634(11) 0.4767(5) -0.4120(6) 0.213(4) Uani 1 1 d . . . F10 F 0.0983(10) 0.4082(3) -0.3177(3) 0.159(3) Uani 1 1 d . . . F11 F 0.2298(6) 0.5021(2) -0.3170(3) 0.1056(17) Uani 1 1 d . . . F12 F 0.1990(9) 0.3842(3) -0.4319(3) 0.145(3) Uani 1 1 d . . . O1 O 0.3306(14) 0.5862(6) -0.5399(7) 0.210(5) Uiso 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 Pt 0.04904(13) 0.04115(13) 0.03810(12) 0.00410(9) 0.00087(8) 0.00024(9) C1 0.097(6) 0.071(5) 0.086(5) 0.018(4) -0.029(4) -0.036(4) S2 0.0996(13) 0.0400(9) 0.0598(10) 0.0066(7) -0.0115(9) -0.0033(8) C3 0.130(7) 0.041(4) 0.059(4) -0.008(3) -0.004(4) 0.008(4) C4 0.126(7) 0.046(4) 0.066(4) -0.001(3) 0.018(4) 0.036(4) S5 0.0555(8) 0.0522(9) 0.0491(8) 0.0078(6) 0.0077(6) 0.0213(7) C6 0.050(3) 0.058(4) 0.038(3) 0.004(2) 0.009(2) 0.018(3) C7 0.042(3) 0.051(3) 0.032(3) 0.003(2) 0.008(2) 0.005(2) C8 0.035(3) 0.079(5) 0.061(4) 0.015(3) 0.006(3) -0.002(3) C9 0.061(4) 0.095(6) 0.057(4) 0.009(4) -0.004(3) -0.027(4) C10 0.091(5) 0.053(4) 0.051(4) 0.005(3) 0.004(3) -0.016(4) C11 0.061(4) 0.053(4) 0.045(3) 0.013(3) 0.007(3) 0.007(3) C12 0.039(3) 0.048(3) 0.035(3) 0.010(2) 0.003(2) 0.003(2) C13 0.043(3) 0.050(3) 0.046(3) 0.008(2) -0.003(2) 0.009(2) S14 0.0335(7) 0.0599(9) 0.0553(8) 0.0062(7) 0.0021(6) 0.0009(6) C15 0.073(4) 0.060(4) 0.055(4) 0.002(3) 0.018(3) 0.018(3) C16 0.081(4) 0.047(4) 0.043(3) -0.005(3) 0.007(3) -0.001(3) S17 0.0512(8) 0.0564(9) 0.0396(7) -0.0025(6) 0.0018(6) -0.0079(6) C18 0.076(4) 0.070(5) 0.038(3) 0.004(3) 0.012(3) -0.004(3) C19 0.065(4) 0.063(4) 0.051(4) 0.019(3) 0.015(3) 0.003(3) C20 0.069(5) 0.082(5) 0.086(5) 0.027(4) 0.035(4) 0.008(4) C21 0.060(5) 0.120(9) 0.128(9) 0.060(7) 0.032(5) -0.003(5) C22 0.060(5) 0.090(6) 0.112(7) 0.046(5) -0.010(4) -0.020(4) C23 0.070(4) 0.051(4) 0.075(4) 0.031(3) -0.014(3) -0.016(3) N24 0.048(3) 0.051(3) 0.053(3) 0.019(2) 0.000(2) -0.007(2) P1 0.0456(8) 0.0519(9) 0.0581(9) -0.0112(7) -0.0019(7) 0.0049(7) F1 0.130(5) 0.329(11) 0.076(4) 0.032(5) 0.007(3) -0.034(6) F2 0.078(3) 0.067(4) 0.363(11) -0.062(5) 0.001(5) 0.010(3) F3 0.160(6) 0.341(12) 0.072(4) 0.006(5) 0.002(4) -0.101(7) F4 0.099(4) 0.062(3) 0.291(8) -0.042(4) -0.088(5) 0.024(3) F5 0.055(2) 0.092(3) 0.141(4) -0.029(3) -0.017(2) 0.001(2) F6 0.058(2) 0.082(3) 0.132(4) -0.012(3) -0.024(2) 0.006(2) P2 0.0777(12) 0.0522(10) 0.0548(9) -0.0064(7) 0.0151(8) -0.0129(8) F7 0.215(8) 0.230(10) 0.181(7) -0.020(6) -0.050(6) 0.138(7) F8 0.232(7) 0.103(4) 0.123(4) -0.021(3) 0.097(5) -0.076(5) F9 0.177(7) 0.233(10) 0.224(9) -0.017(7) -0.099(7) 0.048(7) F10 0.247(8) 0.103(4) 0.134(5) -0.049(4) 0.118(5) -0.092(5) F11 0.124(4) 0.085(3) 0.110(4) -0.042(3) 0.036(3) -0.039(3) F12 0.275(8) 0.080(4) 0.083(3) -0.033(3) 0.079(4) -0.074(4) _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 Pt N24 2.025(5) . ? Pt S2 2.2616(17) . ? Pt S5 2.2979(15) . ? Pt S17 2.3074(15) . ? C1 C23 1.491(11) . ? C1 S2 1.837(8) . ? S2 C3 1.822(7) . ? C3 C4 1.493(11) . ? C4 S5 1.829(7) . ? S5 C6 1.843(5) . ? C6 C7 1.498(8) . ? C7 C8 1.394(8) . ? C7 C12 1.405(7) . ? C8 C9 1.370(10) . ? C9 C10 1.377(10) . ? C10 C11 1.390(9) . ? C11 C12 1.391(8) . ? C12 C13 1.500(7) . ? C13 S14 1.822(5) . ? S14 C15 1.807(7) . ? C15 C16 1.531(8) . ? C16 S17 1.809(6) . ? S17 C18 1.821(6) . ? C18 C19 1.505(9) . ? C19 N24 1.348(8) . ? C19 C20 1.382(9) . ? C20 C21 1.359(13) . ? C21 C22 1.382(13) . ? C22 C23 1.400(10) . ? C23 N24 1.366(8) . ? P1 F3 1.522(6) . ? P1 F4 1.542(5) . ? P1 F1 1.549(6) . ? P1 F2 1.553(5) . ? P1 F5 1.586(4) . ? P1 F6 1.592(4) . ? P2 F7 1.508(7) . ? P2 F9 1.534(7) . ? P2 F10 1.546(5) . ? P2 F8 1.554(5) . ? P2 F11 1.556(4) . ? P2 F12 1.572(5) . ? 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 N24 Pt S2 84.03(15) . . ? N24 Pt S5 171.07(15) . . ? S2 Pt S5 89.59(7) . . ? N24 Pt S17 85.31(15) . . ? S2 Pt S17 163.45(6) . . ? S5 Pt S17 102.24(5) . . ? C23 C1 S2 108.6(5) . . ? C3 S2 C1 109.8(4) . . ? C3 S2 Pt 99.3(2) . . ? C1 S2 Pt 93.3(3) . . ? C4 C3 S2 105.7(5) . . ? C3 C4 S5 113.4(5) . . ? C4 S5 C6 98.3(3) . . ? C4 S5 Pt 100.2(3) . . ? C6 S5 Pt 107.36(18) . . ? C7 C6 S5 112.1(4) . . ? C8 C7 C12 119.3(6) . . ? C8 C7 C6 118.8(5) . . ? C12 C7 C6 121.8(5) . . ? C9 C8 C7 121.5(6) . . ? C8 C9 C10 120.0(6) . . ? C9 C10 C11 119.1(7) . . ? C10 C11 C12 122.0(6) . . ? C11 C12 C7 118.0(5) . . ? C11 C12 C13 119.2(5) . . ? C7 C12 C13 122.7(5) . . ? C12 C13 S14 114.0(4) . . ? C15 S14 C13 102.4(3) . . ? C16 C15 S14 118.0(4) . . ? C15 C16 S17 117.5(5) . . ? C16 S17 C18 102.2(3) . . ? C16 S17 Pt 111.0(2) . . ? C18 S17 Pt 96.8(2) . . ? C19 C18 S17 113.9(4) . . ? N24 C19 C20 120.0(7) . . ? N24 C19 C18 116.8(5) . . ? C20 C19 C18 123.2(7) . . ? C21 C20 C19 119.5(8) . . ? C20 C21 C22 120.9(8) . . ? C21 C22 C23 119.2(8) . . ? N24 C23 C22 118.4(7) . . ? N24 C23 C1 117.2(6) . . ? C22 C23 C1 124.3(7) . . ? C19 N24 C23 122.1(6) . . ? C19 N24 Pt 121.2(4) . . ? C23 N24 Pt 116.6(5) . . ? F3 P1 F4 91.5(5) . . ? F3 P1 F1 179.0(5) . . ? F4 P1 F1 89.2(5) . . ? F3 P1 F2 87.8(5) . . ? F4 P1 F2 179.3(5) . . ? F1 P1 F2 91.4(5) . . ? F3 P1 F5 91.8(4) . . ? F4 P1 F5 91.2(3) . . ? F1 P1 F5 88.8(3) . . ? F2 P1 F5 89.0(3) . . ? F3 P1 F6 88.9(4) . . ? F4 P1 F6 88.8(3) . . ? F1 P1 F6 90.5(3) . . ? F2 P1 F6 90.9(3) . . ? F5 P1 F6 179.3(3) . . ? F7 P2 F9 178.3(5) . . ? F7 P2 F10 90.7(5) . . ? F9 P2 F10 89.5(5) . . ? F7 P2 F8 90.7(5) . . ? F9 P2 F8 89.1(5) . . ? F10 P2 F8 178.5(5) . . ? F7 P2 F11 89.1(4) . . ? F9 P2 F11 89.2(4) . . ? F10 P2 F11 89.1(3) . . ? F8 P2 F11 91.4(3) . . ? F7 P2 F12 91.5(5) . . ? F9 P2 F12 90.1(5) . . ? F10 P2 F12 91.1(3) . . ? F8 P2 F12 88.3(3) . . ? F11 P2 F12 179.3(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.266 _refine_diff_density_min -1.031 _refine_diff_density_rms 0.107 data_kf18 _database_code_CSD 188674 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H25 Cl2 Cu N O9 S4' _chemical_formula_weight 674.08 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 '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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1837(1) _cell_length_b 11.5515(1) _cell_length_c 12.7592(1) _cell_angle_alpha 106.658(1) _cell_angle_beta 115.962(1) _cell_angle_gamma 100.950(1) _cell_volume 1321.17(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic crystal fragment' _exptl_crystal_colour 'Dark red' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method ? _exptl_crystal_F_000 690 _exptl_absorpt_coefficient_mu 1.394 _exptl_absorpt_correction_type 'SADABS (Shedrick, 1996)' _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.749 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10763 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.34 _reflns_number_total 5280 _reflns_number_observed 4493 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+1.1569P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5280 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_obs 0.0413 _refine_ls_wR_factor_all 0.1233 _refine_ls_wR_factor_obs 0.1183 _refine_ls_goodness_of_fit_all 1.064 _refine_ls_goodness_of_fit_obs 1.112 _refine_ls_restrained_S_all 1.064 _refine_ls_restrained_S_obs 1.112 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu 0.24622(4) 0.19409(3) 0.02085(3) 0.03618(13) Uani 1 d . . C1 C 0.4236(5) 0.0635(4) 0.1796(4) 0.0673(12) Uani 1 d . . H1A H 0.3654(5) -0.0216(4) 0.1617(4) 0.081 Uiso 1 calc R . H1B H 0.5229(5) 0.0735(4) 0.2287(4) 0.081 Uiso 1 calc R . S2 S 0.38695(9) 0.06972(8) 0.02877(9) 0.0449(2) Uani 1 d . . C3 C 0.2615(4) -0.0936(3) -0.0866(3) 0.0497(8) Uani 1 d . . H3A H 0.2498(4) -0.1062(3) -0.1695(3) 0.060 Uiso 1 calc R . H3B H 0.3018(4) -0.1549(3) -0.0605(3) 0.060 Uiso 1 calc R . C4 C 0.1152(4) -0.1243(3) -0.1016(4) 0.0531(9) Uani 1 d . . H4A H 0.1243(4) -0.1305(3) -0.0244(4) 0.064 Uiso 1 calc R . H4B H 0.0525(4) -0.2088(3) -0.1725(4) 0.064 Uiso 1 calc R . S5 S 0.03103(8) -0.00760(8) -0.13031(8) 0.0415(2) Uani 1 d . . C6 C -0.0357(4) -0.0462(4) -0.3010(3) 0.0532(9) Uani 1 d . . H6A H -0.1024(4) -0.1354(4) -0.3508(3) 0.064 Uiso 1 calc R . H6B H -0.0895(4) 0.0082(4) -0.3247(3) 0.064 Uiso 1 calc R . C7 C 0.0715(4) -0.0307(3) -0.3415(3) 0.0452(7) Uani 1 d . . C8 C 0.0835(5) -0.1431(4) -0.4097(3) 0.0600(10) Uani 1 d . . H8A H 0.0264(5) -0.2241(4) -0.4268(3) 0.072 Uiso 1 calc R . C9 C 0.1785(5) -0.1354(5) -0.4518(4) 0.0671(11) Uani 1 d . . H9A H 0.1850(5) -0.2107(5) -0.4966(4) 0.081 Uiso 1 calc R . C10 C 0.2637(5) -0.0155(5) -0.4270(4) 0.0670(11) Uani 1 d . . H10A H 0.3280(5) -0.0097(5) -0.4547(4) 0.080 Uiso 1 calc R . C11 C 0.2526(4) 0.0956(4) -0.3610(4) 0.0562(9) Uani 1 d . . H11A H 0.3107(4) 0.1760(4) -0.3442(4) 0.067 Uiso 1 calc R . C12 C 0.1568(4) 0.0903(3) -0.3190(3) 0.0435(7) Uani 1 d . . C13 C 0.1488(4) 0.2165(3) -0.2515(3) 0.0470(8) Uani 1 d . . H13A H 0.0632(4) 0.1998(3) -0.2469(3) 0.056 Uiso 1 calc R . H13B H 0.1452(4) 0.2702(3) -0.2982(3) 0.056 Uiso 1 calc R . S14 S 0.30795(9) 0.29998(8) -0.08955(8) 0.0453(2) Uani 1 d . . C15 C 0.2881(5) 0.4523(3) -0.0233(4) 0.0576(10) Uani 1 d . . H15A H 0.3691(5) 0.5036(3) 0.0636(4) 0.069 Uiso 1 calc R . H15B H 0.2900(5) 0.5007(3) -0.0737(4) 0.069 Uiso 1 calc R . C16 C 0.1518(4) 0.4349(3) -0.0209(4) 0.0538(9) Uani 1 d . . H16A H 0.0715(4) 0.4005(3) -0.1082(4) 0.065 Uiso 1 calc R . H16B H 0.1551(4) 0.5192(3) 0.0260(4) 0.065 Uiso 1 calc R . S17 S 0.12217(9) 0.32772(8) 0.05199(8) 0.0438(2) Uani 1 d . . C18 C 0.2561(4) 0.4222(3) 0.2225(3) 0.0470(8) Uani 1 d . . H18A H 0.3340(4) 0.4880(3) 0.2331(3) 0.056 Uiso 1 calc R . H18B H 0.2137(4) 0.4657(3) 0.2657(3) 0.056 Uiso 1 calc R . C19 C 0.3121(3) 0.3347(3) 0.2809(3) 0.0398(7) Uani 1 d . . C20 C 0.3540(4) 0.3571(4) 0.4070(3) 0.0500(8) Uani 1 d . . H20A H 0.3389(4) 0.4231(4) 0.4558(3) 0.060 Uiso 1 calc R . C21 C 0.4181(4) 0.2805(4) 0.4589(3) 0.0557(9) Uani 1 d . . H21A H 0.4458(4) 0.2939(4) 0.5429(3) 0.067 Uiso 1 calc R . C22 C 0.4408(4) 0.1843(4) 0.3863(3) 0.0529(9) Uani 1 d . . H22A H 0.4858(4) 0.1334(4) 0.4211(3) 0.063 Uiso 1 calc R . C23 C 0.3959(3) 0.1639(3) 0.2603(3) 0.0433(7) Uani 1 d . . N24 N 0.3294(3) 0.2363(2) 0.2080(2) 0.0365(5) Uani 1 d . . Cl1 Cl 0.31495(9) -0.45042(9) -0.29466(8) 0.0515(2) Uani 1 d . . O11 O 0.1809(4) -0.5322(5) -0.3353(6) 0.141(2) Uani 1 d . . O12 O 0.4070(6) -0.5191(6) -0.2761(6) 0.144(2) Uani 1 d . . O13 O 0.3111(5) -0.3994(4) -0.3842(4) 0.1053(13) Uani 1 d . . O14 O 0.3735(8) -0.3505(5) -0.1764(5) 0.172(3) Uani 1 d . . Cl2 Cl 0.72625(10) 0.21192(8) 0.75023(8) 0.0513(2) Uani 1 d . . O21 O 0.8200(5) 0.1440(5) 0.7885(5) 0.134(2) Uani 1 d . . O22 O 0.7014(8) 0.2529(5) 0.8486(7) 0.190(4) Uani 1 d . . O23 O 0.6054(4) 0.1186(4) 0.6348(4) 0.1104(15) Uani 1 d . . O24 O 0.8005(5) 0.3140(4) 0.7367(5) 0.119(2) Uani 1 d . . O31 O 0.9552(5) 0.5770(5) 0.6546(4) 0.1137(14) Uani 1 d . . H31A H 0.9713 0.5469 0.6756 0.080 Uiso 1 d . . H31B H 0.9388 0.5583 0.6211 0.080 Uiso 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 Cu 0.0388(2) 0.0378(2) 0.0336(2) 0.0173(2) 0.0181(2) 0.0159(2) C1 0.092(3) 0.061(2) 0.044(2) 0.025(2) 0.023(2) 0.048(2) S2 0.0420(4) 0.0415(4) 0.0517(5) 0.0184(4) 0.0242(4) 0.0190(3) C3 0.056(2) 0.040(2) 0.046(2) 0.0128(14) 0.024(2) 0.019(2) C4 0.056(2) 0.038(2) 0.056(2) 0.020(2) 0.025(2) 0.009(2) S5 0.0368(4) 0.0445(4) 0.0380(4) 0.0164(3) 0.0192(3) 0.0066(3) C6 0.044(2) 0.057(2) 0.035(2) 0.014(2) 0.0126(14) 0.000(2) C7 0.044(2) 0.051(2) 0.0285(15) 0.0145(14) 0.0138(13) 0.0083(15) C8 0.072(3) 0.050(2) 0.036(2) 0.014(2) 0.018(2) 0.015(2) C9 0.080(3) 0.079(3) 0.041(2) 0.020(2) 0.028(2) 0.042(2) C10 0.062(2) 0.098(3) 0.052(2) 0.033(2) 0.033(2) 0.037(2) C11 0.055(2) 0.070(2) 0.047(2) 0.030(2) 0.028(2) 0.017(2) C12 0.046(2) 0.050(2) 0.0305(15) 0.0193(14) 0.0164(14) 0.0136(15) C13 0.049(2) 0.048(2) 0.035(2) 0.0192(14) 0.0152(14) 0.0132(15) S14 0.0425(4) 0.0486(5) 0.0381(4) 0.0206(4) 0.0184(3) 0.0067(4) C15 0.072(3) 0.040(2) 0.044(2) 0.019(2) 0.023(2) 0.005(2) C16 0.067(2) 0.043(2) 0.044(2) 0.022(2) 0.019(2) 0.025(2) S17 0.0389(4) 0.0434(4) 0.0477(4) 0.0202(4) 0.0196(4) 0.0183(3) C18 0.056(2) 0.044(2) 0.041(2) 0.0157(14) 0.026(2) 0.022(2) C19 0.038(2) 0.040(2) 0.038(2) 0.0152(13) 0.0193(13) 0.0098(13) C20 0.049(2) 0.052(2) 0.038(2) 0.0116(15) 0.022(2) 0.009(2) C21 0.055(2) 0.062(2) 0.036(2) 0.021(2) 0.018(2) 0.009(2) C22 0.051(2) 0.050(2) 0.043(2) 0.025(2) 0.013(2) 0.011(2) C23 0.040(2) 0.037(2) 0.037(2) 0.0153(13) 0.0107(13) 0.0083(13) N24 0.0379(13) 0.0339(12) 0.0323(12) 0.0139(10) 0.0152(11) 0.0107(10) Cl1 0.0487(5) 0.0506(5) 0.0482(5) 0.0193(4) 0.0240(4) 0.0101(4) O11 0.060(2) 0.119(3) 0.220(6) 0.113(4) 0.038(3) 0.010(2) O12 0.129(4) 0.205(6) 0.205(6) 0.146(5) 0.111(4) 0.117(4) O13 0.121(3) 0.116(3) 0.103(3) 0.075(3) 0.061(3) 0.037(3) O14 0.271(8) 0.105(4) 0.093(3) 0.001(3) 0.100(5) 0.027(4) Cl2 0.0517(5) 0.0404(4) 0.0492(5) 0.0140(4) 0.0199(4) 0.0161(4) O21 0.106(3) 0.147(4) 0.151(4) 0.093(4) 0.038(3) 0.078(3) O22 0.239(7) 0.091(3) 0.218(7) -0.031(4) 0.188(6) -0.008(4) O23 0.087(3) 0.101(3) 0.066(2) 0.026(2) 0.001(2) -0.006(2) O24 0.115(3) 0.074(2) 0.181(5) 0.070(3) 0.081(3) 0.024(2) O31 0.096(3) 0.129(4) 0.099(3) 0.027(3) 0.048(3) 0.046(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 Cu N24 2.005(2) . ? Cu S2 2.3139(9) . ? Cu S17 2.3259(9) . ? Cu S14 2.3400(8) . ? Cu S5 2.4838(9) . ? C1 C23 1.494(5) . ? C1 S2 1.810(4) . ? S2 C3 1.813(3) . ? C3 C4 1.517(5) . ? C4 S5 1.817(4) . ? S5 C6 1.842(3) . ? C6 C7 1.500(5) . ? C7 C12 1.404(5) . ? C7 C8 1.407(5) . ? C8 C9 1.385(6) . ? C9 C10 1.382(7) . ? C10 C11 1.379(6) . ? C11 C12 1.392(5) . ? C12 C13 1.507(5) . ? C13 S14 1.831(3) . ? S14 C15 1.823(4) . ? C15 C16 1.514(6) . ? C16 S17 1.812(4) . ? S17 C18 1.825(3) . ? C18 C19 1.494(5) . ? C19 N24 1.353(4) . ? C19 C20 1.390(5) . ? C20 C21 1.377(6) . ? C21 C22 1.371(6) . ? C22 C23 1.387(5) . ? C23 N24 1.348(4) . ? Cl1 O14 1.374(4) . ? Cl1 O11 1.382(4) . ? Cl1 O12 1.397(5) . ? Cl1 O13 1.417(4) . ? Cl2 O22 1.375(5) . ? Cl2 O23 1.397(4) . ? Cl2 O24 1.407(4) . ? Cl2 O21 1.428(4) . ? 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 N24 Cu S2 85.10(8) . . ? N24 Cu S17 84.56(8) . . ? S2 Cu S17 169.66(3) . . ? N24 Cu S14 132.89(7) . . ? S2 Cu S14 97.06(3) . . ? S17 Cu S14 90.01(3) . . ? N24 Cu S5 115.96(7) . . ? S2 Cu S5 88.87(3) . . ? S17 Cu S5 95.62(3) . . ? S14 Cu S5 111.13(3) . . ? C23 C1 S2 114.8(3) . . ? C1 S2 C3 102.1(2) . . ? C1 S2 Cu 97.21(13) . . ? C3 S2 Cu 104.60(12) . . ? C4 C3 S2 114.5(2) . . ? C3 C4 S5 115.4(2) . . ? C4 S5 C6 103.6(2) . . ? C4 S5 Cu 98.26(12) . . ? C6 S5 Cu 114.19(11) . . ? C7 C6 S5 118.0(2) . . ? C12 C7 C8 118.3(3) . . ? C12 C7 C6 123.1(3) . . ? C8 C7 C6 118.6(3) . . ? C9 C8 C7 121.3(4) . . ? C10 C9 C8 119.8(4) . . ? C11 C10 C9 119.6(4) . . ? C10 C11 C12 121.7(4) . . ? C11 C12 C7 119.3(3) . . ? C11 C12 C13 117.9(3) . . ? C7 C12 C13 122.8(3) . . ? C12 C13 S14 108.1(2) . . ? C15 S14 C13 103.2(2) . . ? C15 S14 Cu 98.78(12) . . ? C13 S14 Cu 102.19(12) . . ? C16 C15 S14 113.8(3) . . ? C15 C16 S17 113.7(2) . . ? C16 S17 C18 103.7(2) . . ? C16 S17 Cu 103.15(13) . . ? C18 S17 Cu 93.98(11) . . ? C19 C18 S17 109.8(2) . . ? N24 C19 C20 120.7(3) . . ? N24 C19 C18 116.9(3) . . ? C20 C19 C18 122.2(3) . . ? C21 C20 C19 119.2(3) . . ? C22 C21 C20 119.8(3) . . ? C21 C22 C23 119.3(3) . . ? N24 C23 C22 121.1(3) . . ? N24 C23 C1 118.0(3) . . ? C22 C23 C1 120.9(3) . . ? C23 N24 C19 119.8(3) . . ? C23 N24 Cu 120.8(2) . . ? C19 N24 Cu 119.3(2) . . ? O14 Cl1 O11 111.3(4) . . ? O14 Cl1 O12 105.0(4) . . ? O11 Cl1 O12 108.8(3) . . ? O14 Cl1 O13 109.7(3) . . ? O11 Cl1 O13 111.6(3) . . ? O12 Cl1 O13 110.3(3) . . ? O22 Cl2 O23 113.5(4) . . ? O22 Cl2 O24 113.8(3) . . ? O23 Cl2 O24 113.7(3) . . ? O22 Cl2 O21 104.4(4) . . ? O23 Cl2 O21 104.3(3) . . ? O24 Cl2 O21 105.9(3) . . ? _refine_diff_density_max 1.085 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.077 data_kf22 _database_code_CSD 188675 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 Cu F6 N P S4' _chemical_formula_weight 602.13 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' 'F' 'F' 0.0171 0.0103 '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' 'P' 'P' 0.1023 0.0942 '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' 'Cu' 'Cu' 0.3201 1.2651 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2285(2) _cell_length_b 11.6204(2) _cell_length_c 13.0124(3) _cell_angle_alpha 105.621(1) _cell_angle_beta 101.527(1) _cell_angle_gamma 113.172(1) _cell_volume 1159.45(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic fragment' _exptl_crystal_colour 'Very pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 1.428 _exptl_absorpt_correction_type 'Sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9662 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.38 _reflns_number_total 4705 _reflns_number_gt 3294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0740P)^2^+0.9661P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4705 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1448 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _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 Cu Cu 0.55523(8) 0.74359(6) 0.43344(5) 0.0530(2) Uani 1 1 d . . . C1 C 0.9141(6) 0.9169(5) 0.6430(4) 0.0539(12) Uani 1 1 d . . . H1A H 0.9974 0.9053 0.6914 0.065 Uiso 1 1 calc R . . H1B H 0.9639 1.0116 0.6530 0.065 Uiso 1 1 calc R . . S2 S 0.86887(15) 0.81580(12) 0.49723(10) 0.0492(3) Uani 1 1 d . . . C3 C 0.8338(6) 0.6542(5) 0.5086(4) 0.0493(11) Uani 1 1 d . . . H3A H 0.9404 0.6550 0.5350 0.059 Uiso 1 1 calc R . . H3B H 0.7770 0.6395 0.5626 0.059 Uiso 1 1 calc R . . C4 C 0.7281(6) 0.5430(5) 0.3934(4) 0.0506(11) Uani 1 1 d . . . H4A H 0.7251 0.4590 0.3947 0.061 Uiso 1 1 calc R . . H4B H 0.7785 0.5651 0.3380 0.061 Uiso 1 1 calc R . . S5 S 0.51513(14) 0.51931(11) 0.35086(9) 0.0429(3) Uani 1 1 d . . . C6 C 0.4647(6) 0.4651(5) 0.1969(4) 0.0492(11) Uani 1 1 d . . . H6A H 0.4774 0.3846 0.1694 0.059 Uiso 1 1 calc R . . H6B H 0.3476 0.4396 0.1623 0.059 Uiso 1 1 calc R . . C7 C 0.5688(5) 0.5683(4) 0.1573(3) 0.0431(10) Uani 1 1 d . . . C8 C 0.7027(6) 0.5585(5) 0.1304(4) 0.0532(12) Uani 1 1 d . . . H8A H 0.7243 0.4885 0.1368 0.064 Uiso 1 1 calc R . . C9 C 0.8047(6) 0.6512(6) 0.0943(4) 0.0636(14) Uani 1 1 d . . . H9A H 0.8939 0.6432 0.0766 0.076 Uiso 1 1 calc R . . C10 C 0.7739(7) 0.7542(6) 0.0848(4) 0.0660(15) Uani 1 1 d . . . H10A H 0.8435 0.8177 0.0621 0.079 Uiso 1 1 calc R . . C11 C 0.6399(7) 0.7637(5) 0.1090(4) 0.0570(13) Uani 1 1 d . . . H11A H 0.6187 0.8334 0.1013 0.068 Uiso 1 1 calc R . . C12 C 0.5356(5) 0.6719(4) 0.1446(3) 0.0440(10) Uani 1 1 d . . . C13 C 0.3915(6) 0.6883(5) 0.1686(4) 0.0523(11) Uani 1 1 d . . . H13A H 0.3096 0.6047 0.1688 0.063 Uiso 1 1 calc R . . H13B H 0.3369 0.7098 0.1102 0.063 Uiso 1 1 calc R . . S14 S 0.47235(15) 0.82549(11) 0.30718(10) 0.0466(3) Uani 1 1 d . . . C15 C 0.2816(6) 0.8264(5) 0.3215(5) 0.0583(13) Uani 1 1 d . . . H15A H 0.3127 0.9064 0.3872 0.070 Uiso 1 1 calc R . . H15B H 0.2251 0.8355 0.2552 0.070 Uiso 1 1 calc R . . C16 C 0.1573(6) 0.7039(5) 0.3344(4) 0.0543(12) Uani 1 1 d . . . H16A H 0.1055 0.6277 0.2617 0.065 Uiso 1 1 calc R . . H16B H 0.0693 0.7224 0.3516 0.065 Uiso 1 1 calc R . . S17 S 0.24083(15) 0.65305(12) 0.44178(10) 0.0499(3) Uani 1 1 d . . . C18 C 0.3224(6) 0.8025(5) 0.5710(4) 0.0583(13) Uani 1 1 d . . . H18A H 0.3365 0.8798 0.5509 0.070 Uiso 1 1 calc R . . H18B H 0.2411 0.7885 0.6097 0.070 Uiso 1 1 calc R . . C19 C 0.4881(5) 0.8342(4) 0.6512(4) 0.0437(10) Uani 1 1 d . . . C20 C 0.5131(7) 0.8657(5) 0.7658(4) 0.0562(12) Uani 1 1 d . . . H20A H 0.4257 0.8612 0.7928 0.067 Uiso 1 1 calc R . . C21 C 0.6670(7) 0.9036(5) 0.8387(4) 0.0608(13) Uani 1 1 d . . . H21A H 0.6849 0.9223 0.9157 0.073 Uiso 1 1 calc R . . C22 C 0.7952(6) 0.9140(5) 0.7974(4) 0.0530(12) Uani 1 1 d . . . H22A H 0.9011 0.9401 0.8462 0.064 Uiso 1 1 calc R . . C23 C 0.7660(6) 0.8854(4) 0.6835(4) 0.0444(10) Uani 1 1 d . . . N24 N 0.6124(4) 0.8398(3) 0.6089(3) 0.0408(8) Uani 1 1 d . . . P P -0.10106(16) 0.26983(13) 0.13104(11) 0.0501(3) Uani 1 1 d . . . F1 F 0.0855(5) 0.3348(5) 0.2133(4) 0.1247(16) Uani 1 1 d . . . F2 F -0.0575(6) 0.1913(4) 0.0371(4) 0.142(2) Uani 1 1 d . . . F3 F -0.2863(5) 0.2099(5) 0.0546(4) 0.1149(15) Uani 1 1 d . . . F4 F -0.1395(5) 0.3529(4) 0.2295(4) 0.1076(13) Uani 1 1 d . . . F5 F -0.1587(5) 0.1478(4) 0.1707(4) 0.1118(15) Uani 1 1 d . . . F6 F -0.0434(5) 0.3948(4) 0.0935(4) 0.1051(13) 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 Cu 0.0674(4) 0.0617(4) 0.0365(3) 0.0161(3) 0.0110(3) 0.0419(3) C1 0.046(3) 0.054(3) 0.055(3) 0.018(2) 0.012(2) 0.022(2) S2 0.0501(7) 0.0495(7) 0.0495(7) 0.0222(5) 0.0193(5) 0.0219(5) C3 0.053(3) 0.053(3) 0.046(3) 0.022(2) 0.016(2) 0.029(2) C4 0.061(3) 0.056(3) 0.044(2) 0.021(2) 0.014(2) 0.037(2) S5 0.0504(6) 0.0415(6) 0.0393(6) 0.0201(5) 0.0161(5) 0.0210(5) C6 0.056(3) 0.044(2) 0.036(2) 0.0129(19) 0.008(2) 0.018(2) C7 0.049(3) 0.043(2) 0.0262(19) 0.0100(17) 0.0072(18) 0.017(2) C8 0.057(3) 0.063(3) 0.035(2) 0.015(2) 0.012(2) 0.029(2) C9 0.052(3) 0.091(4) 0.040(3) 0.020(3) 0.018(2) 0.028(3) C10 0.063(3) 0.069(4) 0.044(3) 0.024(3) 0.022(2) 0.008(3) C11 0.072(3) 0.051(3) 0.040(3) 0.021(2) 0.018(2) 0.020(3) C12 0.046(2) 0.047(2) 0.027(2) 0.0137(18) 0.0049(17) 0.015(2) C13 0.057(3) 0.060(3) 0.038(2) 0.022(2) 0.007(2) 0.028(2) S14 0.0536(7) 0.0406(6) 0.0469(6) 0.0201(5) 0.0134(5) 0.0234(5) C15 0.070(3) 0.059(3) 0.067(3) 0.031(3) 0.023(3) 0.046(3) C16 0.047(3) 0.061(3) 0.059(3) 0.022(2) 0.014(2) 0.031(2) S17 0.0505(7) 0.0432(6) 0.0483(7) 0.0148(5) 0.0132(5) 0.0187(5) C18 0.050(3) 0.056(3) 0.052(3) 0.003(2) 0.015(2) 0.022(2) C19 0.044(2) 0.036(2) 0.046(2) 0.0143(19) 0.015(2) 0.0153(19) C20 0.065(3) 0.045(3) 0.056(3) 0.019(2) 0.034(3) 0.019(2) C21 0.078(4) 0.052(3) 0.037(3) 0.014(2) 0.014(3) 0.021(3) C22 0.060(3) 0.044(3) 0.041(2) 0.013(2) 0.006(2) 0.020(2) C23 0.051(3) 0.035(2) 0.041(2) 0.0125(18) 0.008(2) 0.020(2) N24 0.043(2) 0.0371(19) 0.0406(19) 0.0130(15) 0.0136(16) 0.0196(16) P 0.0485(7) 0.0528(7) 0.0536(7) 0.0228(6) 0.0212(6) 0.0249(6) F1 0.057(2) 0.151(4) 0.137(4) 0.053(3) 0.012(2) 0.034(2) F2 0.159(4) 0.090(3) 0.147(4) 0.001(3) 0.114(4) 0.031(3) F3 0.067(2) 0.144(4) 0.106(3) 0.065(3) -0.004(2) 0.029(2) F4 0.120(3) 0.097(3) 0.102(3) 0.019(2) 0.069(3) 0.047(2) F5 0.104(3) 0.116(3) 0.193(4) 0.117(3) 0.082(3) 0.071(3) F6 0.125(3) 0.087(3) 0.132(3) 0.071(3) 0.068(3) 0.047(2) _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 Cu N24 2.103(3) . ? Cu S14 2.2590(12) . ? Cu S5 2.3786(12) . ? Cu S2 2.5542(13) . ? Cu S17 2.7059(14) . ? C1 C23 1.509(6) . ? C1 S2 1.803(5) . ? S2 C3 1.829(5) . ? C3 C4 1.499(6) . ? C4 S5 1.818(5) . ? S5 C6 1.828(4) . ? C6 C7 1.501(6) . ? C7 C8 1.387(6) . ? C7 C12 1.395(6) . ? C8 C9 1.385(7) . ? C9 C10 1.364(8) . ? C10 C11 1.373(7) . ? C11 C12 1.385(6) . ? C12 C13 1.495(6) . ? C13 S14 1.824(5) . ? S14 C15 1.811(5) . ? C15 C16 1.514(7) . ? C16 S17 1.808(5) . ? S17 C18 1.818(5) . ? C18 C19 1.509(6) . ? C19 N24 1.355(5) . ? C19 C20 1.384(6) . ? C20 C21 1.363(7) . ? C21 C22 1.371(7) . ? C22 C23 1.373(6) . ? C23 N24 1.347(5) . ? P F2 1.540(4) . ? P F3 1.552(4) . ? P F5 1.572(4) . ? P F4 1.576(4) . ? P F1 1.576(4) . ? P F6 1.584(4) . ? 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 N24 Cu S14 122.05(10) . . ? N24 Cu S5 122.00(10) . . ? S14 Cu S5 114.65(4) . . ? N24 Cu S2 82.09(10) . . ? S14 Cu S2 114.31(5) . . ? S5 Cu S2 85.77(4) . . ? N24 Cu S17 80.27(10) . . ? S14 Cu S17 86.43(4) . . ? S5 Cu S17 92.43(4) . . ? S2 Cu S17 157.94(4) . . ? C23 C1 S2 115.8(3) . . ? C1 S2 C3 100.1(2) . . ? C1 S2 Cu 95.41(16) . . ? C3 S2 Cu 92.59(15) . . ? C4 C3 S2 108.3(3) . . ? C3 C4 S5 111.5(3) . . ? C4 S5 C6 100.0(2) . . ? C4 S5 Cu 102.66(15) . . ? C6 S5 Cu 111.05(15) . . ? C7 C6 S5 115.6(3) . . ? C8 C7 C12 118.7(4) . . ? C8 C7 C6 118.1(4) . . ? C12 C7 C6 123.1(4) . . ? C9 C8 C7 121.1(5) . . ? C10 C9 C8 119.9(5) . . ? C9 C10 C11 119.7(5) . . ? C10 C11 C12 121.5(5) . . ? C11 C12 C7 119.1(4) . . ? C11 C12 C13 118.3(4) . . ? C7 C12 C13 122.6(4) . . ? C12 C13 S14 108.3(3) . . ? C15 S14 C13 101.6(2) . . ? C15 S14 Cu 105.90(16) . . ? C13 S14 Cu 104.82(15) . . ? C16 C15 S14 116.6(3) . . ? C15 C16 S17 116.3(3) . . ? C16 S17 C18 102.2(2) . . ? C16 S17 Cu 97.20(16) . . ? C18 S17 Cu 88.26(16) . . ? C19 C18 S17 112.8(3) . . ? N24 C19 C20 122.0(4) . . ? N24 C19 C18 118.2(4) . . ? C20 C19 C18 119.7(4) . . ? C21 C20 C19 119.3(5) . . ? C20 C21 C22 119.3(4) . . ? C21 C22 C23 119.5(5) . . ? N24 C23 C22 122.2(4) . . ? N24 C23 C1 119.3(4) . . ? C22 C23 C1 118.3(4) . . ? C23 N24 C19 117.6(4) . . ? C23 N24 Cu 120.9(3) . . ? C19 N24 Cu 120.3(3) . . ? F2 P F3 93.6(3) . . ? F2 P F5 90.7(3) . . ? F3 P F5 88.3(2) . . ? F2 P F4 178.2(3) . . ? F3 P F4 88.2(3) . . ? F5 P F4 89.7(2) . . ? F2 P F1 89.1(3) . . ? F3 P F1 177.3(3) . . ? F5 P F1 91.7(2) . . ? F4 P F1 89.2(3) . . ? F2 P F6 90.6(2) . . ? F3 P F6 91.7(2) . . ? F5 P F6 178.7(2) . . ? F4 P F6 89.0(2) . . ? F1 P F6 88.1(2) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.777 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.088 data_kf26 _database_code_CSD 188676 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H23 Cl2 N Ni S4' _chemical_formula_weight 523.23 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8184(1) _cell_length_b 24.2113(1) _cell_length_c 11.6019(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.306(1) _cell_angle_gamma 90.00 _cell_volume 2145.71(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic crystal fragment' _exptl_crystal_colour Green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method ? _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 1.548 _exptl_absorpt_correction_type 'Sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.956 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13063 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.17 _reflns_number_total 4722 _reflns_number_observed 3754 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+1.5353P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4721 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_obs 0.0382 _refine_ls_wR_factor_all 0.0831 _refine_ls_wR_factor_obs 0.0757 _refine_ls_goodness_of_fit_all 1.075 _refine_ls_goodness_of_fit_obs 1.118 _refine_ls_restrained_S_all 1.088 _refine_ls_restrained_S_obs 1.118 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni Ni 0.89941(4) 0.140656(14) 0.42664(3) 0.03681(10) Uani 1 d . . Cl1 Cl 0.88406(11) 0.17554(4) 0.61546(7) 0.0579(2) Uani 1 d . . Cl2 Cl 0.65878(9) 0.08010(3) 0.41151(7) 0.0501(2) Uani 1 d . . C1 C 1.2908(4) 0.12455(13) 0.5591(3) 0.0538(8) Uani 1 d . . H1A H 1.3071(4) 0.13305(13) 0.6424(3) 0.065 Uiso 1 calc R . H1B H 1.3967(4) 0.10648(13) 0.5477(3) 0.065 Uiso 1 calc R . S2 S 1.11271(10) 0.07594(3) 0.52145(7) 0.0467(2) Uani 1 d . . C3 C 1.1725(4) 0.03807(12) 0.4018(3) 0.0500(7) Uani 1 d . . H3A H 1.2876(4) 0.02200(12) 0.4296(3) 0.060 Uiso 1 calc R . H3B H 1.0902(4) 0.00799(12) 0.3794(3) 0.060 Uiso 1 calc R . C4 C 1.1755(4) 0.07268(12) 0.2942(3) 0.0448(7) Uani 1 d . . H4A H 1.2012(4) 0.04882(12) 0.2329(3) 0.054 Uiso 1 calc R . H4B H 1.2701(4) 0.09925(12) 0.3139(3) 0.054 Uiso 1 calc R . S5 S 0.97490(9) 0.10950(3) 0.23592(6) 0.0392(2) Uani 1 d . . C6 C 0.8295(4) 0.05487(12) 0.1643(3) 0.0478(7) Uani 1 d . . H6A H 0.8909(4) 0.01983(12) 0.1762(3) 0.057 Uiso 1 calc R . H6B H 0.7292(4) 0.05246(12) 0.2009(3) 0.057 Uiso 1 calc R . C7 C 0.7666(4) 0.06483(11) 0.0335(3) 0.0443(7) Uani 1 d . . C8 C 0.8916(4) 0.06545(13) -0.0368(3) 0.0545(8) Uani 1 d . . H8A H 1.0093(4) 0.06202(13) -0.0007(3) 0.065 Uiso 1 calc R . C9 C 0.8464(5) 0.07094(14) -0.1567(3) 0.0643(9) Uani 1 d . . H9A H 0.9326(5) 0.07249(14) -0.2008(3) 0.077 Uiso 1 calc R . C10 C 0.6731(6) 0.07415(15) -0.2114(3) 0.0686(10) Uani 1 d . . H10A H 0.6404(6) 0.07594(15) -0.2932(3) 0.082 Uiso 1 calc R . C11 C 0.5481(5) 0.07469(14) -0.1443(3) 0.0662(10) Uani 1 d . . H11A H 0.4309(5) 0.07739(14) -0.1821(3) 0.079 Uiso 1 calc R . C12 C 0.5906(4) 0.07133(12) -0.0211(3) 0.0506(8) Uani 1 d . . C13 C 0.4450(4) 0.07587(14) 0.0452(4) 0.0651(10) Uani 1 d . . H13A H 0.4908(4) 0.06602(14) 0.1270(4) 0.078 Uiso 1 calc R . H13B H 0.3548(4) 0.04926(14) 0.0128(4) 0.078 Uiso 1 calc R . S14 S 0.34522(10) 0.14435(4) 0.04023(8) 0.0602(2) Uani 1 d . . C15 C 0.4524(4) 0.17501(14) 0.1793(3) 0.0574(8) Uani 1 d . . H15A H 0.3774(4) 0.20359(14) 0.2001(3) 0.069 Uiso 1 calc R . H15B H 0.4675(4) 0.14694(14) 0.2403(3) 0.069 Uiso 1 calc R . C16 C 0.6280(4) 0.19972(13) 0.1766(3) 0.0479(7) Uani 1 d . . H16A H 0.6130(4) 0.23246(13) 0.1273(3) 0.058 Uiso 1 calc R . H16B H 0.6982(4) 0.17335(13) 0.1440(3) 0.058 Uiso 1 calc R . S17 S 0.73814(10) 0.21785(3) 0.32781(7) 0.0460(2) Uani 1 d . . C18 C 0.9225(4) 0.25482(13) 0.2964(3) 0.0598(9) Uani 1 d . . H18A H 0.9288(4) 0.24752(13) 0.2152(3) 0.072 Uiso 1 calc R . H18B H 0.9016(4) 0.29406(13) 0.3030(3) 0.072 Uiso 1 calc R . C19 C 1.0950(4) 0.24122(11) 0.3734(2) 0.0434(7) Uani 1 d . . C20 C 1.2345(4) 0.27748(13) 0.3826(3) 0.0550(8) Uani 1 d . . H20A H 1.2186(4) 0.31174(13) 0.3456(3) 0.066 Uiso 1 calc R . C21 C 1.3952(4) 0.26260(15) 0.4461(3) 0.0631(10) Uani 1 d . . H21A H 1.4895(4) 0.28668(15) 0.4529(3) 0.076 Uiso 1 calc R . C22 C 1.4170(4) 0.21203(14) 0.5000(3) 0.0528(8) Uani 1 d . . H22A H 1.5269(4) 0.20073(14) 0.5410(3) 0.063 Uiso 1 calc R . C23 C 1.2723(4) 0.17784(12) 0.4924(2) 0.0411(6) Uani 1 d . . N24 N 1.1139(3) 0.19204(9) 0.4289(2) 0.0379(5) Uani 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 Ni 0.0352(2) 0.0383(2) 0.0374(2) 0.00673(15) 0.00895(14) -0.00223(14) Cl1 0.0664(5) 0.0687(5) 0.0428(4) -0.0048(4) 0.0211(4) -0.0104(4) Cl2 0.0400(4) 0.0494(4) 0.0623(5) 0.0104(3) 0.0140(3) -0.0070(3) C1 0.045(2) 0.062(2) 0.048(2) 0.0030(15) -0.0048(14) 0.0001(14) S2 0.0459(4) 0.0483(4) 0.0454(4) 0.0162(3) 0.0088(3) 0.0011(3) C3 0.046(2) 0.041(2) 0.061(2) 0.0065(14) 0.0077(14) 0.0072(13) C4 0.0360(15) 0.047(2) 0.051(2) 0.0008(13) 0.0089(13) 0.0020(12) S5 0.0392(4) 0.0382(4) 0.0391(4) 0.0012(3) 0.0056(3) 0.0002(3) C6 0.047(2) 0.045(2) 0.050(2) -0.0026(14) 0.0067(14) -0.0061(13) C7 0.046(2) 0.0361(15) 0.048(2) -0.0052(12) 0.0036(13) -0.0006(12) C8 0.052(2) 0.055(2) 0.055(2) -0.0051(15) 0.007(2) 0.0104(15) C9 0.086(3) 0.055(2) 0.056(2) -0.002(2) 0.023(2) 0.018(2) C10 0.093(3) 0.058(2) 0.046(2) -0.004(2) -0.002(2) 0.021(2) C11 0.063(2) 0.055(2) 0.067(2) 0.002(2) -0.018(2) 0.004(2) C12 0.046(2) 0.038(2) 0.064(2) -0.0005(14) 0.0015(15) 0.0002(13) C13 0.046(2) 0.052(2) 0.096(3) 0.005(2) 0.011(2) -0.0045(15) S14 0.0402(4) 0.0649(6) 0.0700(6) 0.0008(4) -0.0006(4) 0.0077(4) C15 0.048(2) 0.065(2) 0.061(2) 0.009(2) 0.015(2) 0.001(2) C16 0.043(2) 0.054(2) 0.046(2) 0.0095(14) 0.0087(13) 0.0072(13) S17 0.0481(4) 0.0432(4) 0.0470(4) 0.0050(3) 0.0109(3) 0.0072(3) C18 0.069(2) 0.046(2) 0.058(2) 0.015(2) 0.001(2) -0.014(2) C19 0.057(2) 0.039(2) 0.038(2) -0.0026(12) 0.0189(13) -0.0074(13) C20 0.069(2) 0.041(2) 0.064(2) -0.0019(15) 0.035(2) -0.013(2) C21 0.052(2) 0.058(2) 0.089(3) -0.018(2) 0.035(2) -0.019(2) C22 0.040(2) 0.066(2) 0.055(2) -0.017(2) 0.0168(14) -0.0089(14) C23 0.0373(14) 0.049(2) 0.0375(15) -0.0039(12) 0.0096(12) -0.0050(12) N24 0.0436(13) 0.0395(13) 0.0323(11) -0.0012(10) 0.0117(10) -0.0062(10) _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 Ni N24 2.084(2) . ? Ni Cl2 2.3621(8) . ? Ni Cl1 2.3746(8) . ? Ni S2 2.3799(8) . ? Ni S17 2.4045(8) . ? Ni S5 2.5239(8) . ? C1 C23 1.496(4) . ? C1 S2 1.804(3) . ? S2 C3 1.806(3) . ? C3 C4 1.508(4) . ? C4 S5 1.805(3) . ? S5 C6 1.825(3) . ? C6 C7 1.512(4) . ? C7 C12 1.396(4) . ? C7 C8 1.399(4) . ? C8 C9 1.367(5) . ? C9 C10 1.370(5) . ? C10 C11 1.373(5) . ? C11 C12 1.399(5) . ? C12 C13 1.508(5) . ? C13 S14 1.828(3) . ? S14 C15 1.811(3) . ? C15 C16 1.504(4) . ? C16 S17 1.835(3) . ? S17 C18 1.799(3) . ? C18 C19 1.488(4) . ? C19 N24 1.347(3) . ? C19 C20 1.387(4) . ? C20 C21 1.362(5) . ? C21 C22 1.369(5) . ? C22 C23 1.389(4) . ? C23 N24 1.344(3) . ? 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 N24 Ni Cl2 176.10(6) . . ? N24 Ni Cl1 88.55(6) . . ? Cl2 Ni Cl1 95.35(3) . . ? N24 Ni S2 84.52(7) . . ? Cl2 Ni S2 95.41(3) . . ? Cl1 Ni S2 88.62(3) . . ? N24 Ni S17 83.15(7) . . ? Cl2 Ni S17 96.81(3) . . ? Cl1 Ni S17 92.24(3) . . ? S2 Ni S17 167.61(3) . . ? N24 Ni S5 81.47(6) . . ? Cl2 Ni S5 94.63(3) . . ? Cl1 Ni S5 169.21(3) . . ? S2 Ni S5 86.37(3) . . ? S17 Ni S5 90.64(3) . . ? C23 C1 S2 116.9(2) . . ? C1 S2 C3 101.8(2) . . ? C1 S2 Ni 96.39(10) . . ? C3 S2 Ni 104.46(10) . . ? C4 C3 S2 114.0(2) . . ? C3 C4 S5 114.8(2) . . ? C4 S5 C6 102.69(14) . . ? C4 S5 Ni 99.56(10) . . ? C6 S5 Ni 112.12(10) . . ? C7 C6 S5 112.3(2) . . ? C12 C7 C8 118.5(3) . . ? C12 C7 C6 123.5(3) . . ? C8 C7 C6 117.9(3) . . ? C9 C8 C7 122.2(3) . . ? C8 C9 C10 119.5(4) . . ? C9 C10 C11 119.4(3) . . ? C10 C11 C12 122.4(3) . . ? C7 C12 C11 117.8(3) . . ? C7 C12 C13 123.7(3) . . ? C11 C12 C13 118.4(3) . . ? C12 C13 S14 114.4(2) . . ? C15 S14 C13 103.3(2) . . ? C16 C15 S14 113.3(2) . . ? C15 C16 S17 108.7(2) . . ? C18 S17 C16 99.11(15) . . ? C18 S17 Ni 97.01(11) . . ? C16 S17 Ni 111.19(10) . . ? C19 C18 S17 115.5(2) . . ? N24 C19 C20 121.3(3) . . ? N24 C19 C18 118.4(2) . . ? C20 C19 C18 120.3(3) . . ? C21 C20 C19 119.6(3) . . ? C20 C21 C22 119.6(3) . . ? C21 C22 C23 118.9(3) . . ? N24 C23 C22 121.7(3) . . ? N24 C23 C1 118.7(2) . . ? C22 C23 C1 119.6(3) . . ? C23 N24 C19 118.9(2) . . ? C23 N24 Ni 120.0(2) . . ? C19 N24 Ni 121.1(2) . . ? _refine_diff_density_max 0.329 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.057 data_kf15 _database_code_CSD 188677 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H23 N S4' _chemical_formula_weight 393.62 _chemical_melting_point ? _chemical_compound_source ? 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 18.2741(7) _cell_length_b 4.7815(2) _cell_length_c 22.8791(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.884(1) _cell_angle_gamma 90.00 _cell_volume 1980.22(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic fragment' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method ? _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type 'Sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 0.977 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10990 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.09 _reflns_number_total 4322 _reflns_number_observed 2975 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.5464P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4320 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_obs 0.0490 _refine_ls_wR_factor_all 0.1331 _refine_ls_wR_factor_obs 0.1012 _refine_ls_goodness_of_fit_all 1.033 _refine_ls_goodness_of_fit_obs 1.065 _refine_ls_restrained_S_all 1.151 _refine_ls_restrained_S_obs 1.065 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.0719(2) 1.1605(7) 0.10489(14) 0.0567(8) Uani 1 d . . H1A H 0.0341(2) 1.2786(7) 0.08357(14) 0.068 Uiso 1 calc R . H1B H 0.1077(2) 1.2821(7) 0.12748(14) 0.068 Uiso 1 calc R . S2 S 0.02958(4) 0.9454(2) 0.15561(4) 0.0636(2) Uani 1 d . . C3 C 0.1057(2) 0.8785(10) 0.21327(15) 0.0965(15) Uani 1 d . . H3A H 0.1065(2) 0.6807(10) 0.22269(15) 0.116 Uiso 1 calc R . H3B H 0.1516(2) 0.9224(10) 0.19836(15) 0.116 Uiso 1 calc R . C4 C 0.1027(2) 1.0363(9) 0.26695(15) 0.0755(10) Uani 1 d . . H4A H 0.0567(2) 0.9925(9) 0.28155(15) 0.091 Uiso 1 calc R . H4B H 0.1017(2) 1.2339(9) 0.25726(15) 0.091 Uiso 1 calc R . S5 S 0.17780(6) 0.9754(3) 0.32568(4) 0.0825(3) Uani 1 d . . C6 C 0.2484(2) 1.2043(8) 0.30551(14) 0.0671(9) Uani 1 d . . H6A H 0.2635(2) 1.1420(8) 0.26861(14) 0.081 Uiso 1 calc R . H6B H 0.2289(2) 1.3925(8) 0.29985(14) 0.081 Uiso 1 calc R . C7 C 0.3146(2) 1.2051(7) 0.35335(13) 0.0521(7) Uani 1 d . . C8 C 0.3115(2) 1.3628(8) 0.4038(2) 0.0720(10) Uani 1 d . . H8A H 0.2688(2) 1.4631(8) 0.4074(2) 0.086 Uiso 1 calc R . C9 C 0.3698(2) 1.3752(8) 0.4484(2) 0.0777(11) Uani 1 d . . H9A H 0.3665(2) 1.4839(8) 0.4817(2) 0.093 Uiso 1 calc R . C10 C 0.4333(2) 1.2252(8) 0.44378(14) 0.0714(10) Uani 1 d . . H10A H 0.4730(2) 1.2311(8) 0.47392(14) 0.086 Uiso 1 calc R . C11 C 0.4373(2) 1.0667(7) 0.39395(13) 0.0570(8) Uani 1 d . . H11A H 0.4801(2) 0.9661(7) 0.39087(13) 0.068 Uiso 1 calc R . C12 C 0.37878(15) 1.0535(6) 0.34816(11) 0.0445(6) Uani 1 d . . C13 C 0.3871(2) 0.8881(6) 0.29355(12) 0.0515(7) Uani 1 d . . H13A H 0.3419(2) 0.7865(6) 0.28034(12) 0.062 Uiso 1 calc R . H13B H 0.4271(2) 0.7543(6) 0.30182(12) 0.062 Uiso 1 calc R . S14 S 0.40699(4) 1.1325(2) 0.23672(3) 0.0497(2) Uani 1 d . . C15 C 0.41060(15) 0.8998(6) 0.17486(12) 0.0475(7) Uani 1 d . . H15A H 0.43244(15) 0.9983(6) 0.14446(12) 0.057 Uiso 1 calc R . H15B H 0.44233(15) 0.7425(6) 0.18766(12) 0.057 Uiso 1 calc R . C16 C 0.33594(14) 0.7917(6) 0.14898(12) 0.0474(7) Uani 1 d . . H16A H 0.30252(14) 0.9472(6) 0.13880(12) 0.057 Uiso 1 calc R . H16B H 0.31571(14) 0.6761(6) 0.17771(12) 0.057 Uiso 1 calc R . S17 S 0.34486(4) 0.5875(2) 0.08346(3) 0.0493(2) Uani 1 d . . C18 C 0.25127(15) 0.4537(6) 0.06803(13) 0.0485(7) Uani 1 d . . H18A H 0.25045(15) 0.3005(6) 0.04015(13) 0.058 Uiso 1 calc R . H18B H 0.23676(15) 0.3796(6) 0.10421(13) 0.058 Uiso 1 calc R . C19 C 0.19580(14) 0.6702(6) 0.04329(11) 0.0423(6) Uani 1 d . . C20 C 0.1834(2) 0.7215(7) -0.01688(12) 0.0541(8) Uani 1 d . . H20A H 0.2092(2) 0.6225(7) -0.04244(12) 0.065 Uiso 1 calc R . C21 C 0.1323(2) 0.9208(8) -0.03831(13) 0.0603(9) Uani 1 d . . H21A H 0.1232(2) 0.9593(8) -0.07850(13) 0.072 Uiso 1 calc R . C22 C 0.09477(15) 1.0626(7) 0.00098(13) 0.0548(8) Uani 1 d . . H22A H 0.05961(15) 1.1968(7) -0.01249(13) 0.066 Uiso 1 calc R . C23 C 0.11004(14) 1.0029(6) 0.06074(12) 0.0454(6) Uani 1 d . . N24 N 0.15982(12) 0.8069(5) 0.08182(9) 0.0432(5) Uani 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 C1 0.051(2) 0.054(2) 0.066(2) 0.003(2) 0.0116(14) -0.0017(15) S2 0.0514(4) 0.0870(6) 0.0537(5) 0.0105(4) 0.0121(4) 0.0066(4) C3 0.110(3) 0.123(4) 0.052(2) -0.005(2) -0.005(2) 0.067(3) C4 0.059(2) 0.100(3) 0.069(2) -0.013(2) 0.011(2) 0.002(2) S5 0.0800(6) 0.1110(8) 0.0539(5) 0.0146(5) -0.0004(4) -0.0252(6) C6 0.052(2) 0.083(3) 0.067(2) 0.017(2) 0.008(2) 0.012(2) C7 0.053(2) 0.057(2) 0.048(2) 0.0031(14) 0.0135(13) 0.0035(15) C8 0.078(2) 0.075(2) 0.067(2) -0.004(2) 0.028(2) 0.012(2) C9 0.112(3) 0.072(3) 0.052(2) -0.018(2) 0.025(2) -0.010(2) C10 0.084(2) 0.079(3) 0.048(2) -0.002(2) -0.001(2) -0.018(2) C11 0.053(2) 0.063(2) 0.054(2) 0.005(2) 0.0048(14) -0.002(2) C12 0.050(2) 0.043(2) 0.0406(14) 0.0028(12) 0.0081(12) -0.0016(13) C13 0.062(2) 0.044(2) 0.049(2) 0.0013(13) 0.0108(14) 0.0025(14) S14 0.0574(4) 0.0442(4) 0.0489(4) -0.0052(3) 0.0122(3) -0.0069(3) C15 0.0459(15) 0.054(2) 0.0435(14) -0.0057(13) 0.0085(12) 0.0004(13) C16 0.0443(15) 0.052(2) 0.0449(15) -0.0038(13) 0.0025(12) 0.0024(13) S17 0.0424(4) 0.0589(5) 0.0462(4) -0.0060(3) 0.0051(3) -0.0014(3) C18 0.049(2) 0.044(2) 0.051(2) -0.0033(13) 0.0042(13) -0.0074(13) C19 0.0392(14) 0.044(2) 0.0430(14) -0.0022(12) 0.0038(11) -0.0116(12) C20 0.047(2) 0.073(2) 0.042(2) -0.0023(15) 0.0076(13) -0.009(2) C21 0.050(2) 0.087(3) 0.042(2) 0.013(2) -0.0004(13) -0.010(2) C22 0.0386(14) 0.063(2) 0.060(2) 0.017(2) -0.0004(13) -0.0038(14) C23 0.0388(14) 0.045(2) 0.053(2) 0.0043(13) 0.0070(12) -0.0085(12) N24 0.0428(12) 0.0439(13) 0.0432(12) 0.0030(10) 0.0068(10) -0.0059(10) _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 C1 C23 1.505(4) . ? C1 S2 1.803(3) . ? S2 C3 1.810(3) . ? C3 C4 1.449(5) . ? C4 S5 1.808(3) . ? S5 C6 1.800(3) . ? C6 C7 1.515(4) . ? C7 C8 1.386(4) . ? C7 C12 1.398(4) . ? C8 C9 1.372(5) . ? C9 C10 1.381(5) . ? C10 C11 1.379(4) . ? C11 C12 1.392(4) . ? C12 C13 1.504(4) . ? C13 S14 1.822(3) . ? S14 C15 1.809(3) . ? C15 C16 1.502(4) . ? C16 S17 1.815(3) . ? S17 C18 1.815(3) . ? C18 C19 1.504(4) . ? C19 N24 1.340(3) . ? C19 C20 1.386(4) . ? C20 C21 1.377(4) . ? C21 C22 1.381(4) . ? C22 C23 1.387(4) . ? C23 N24 1.349(3) . ? 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 C23 C1 S2 115.2(2) . . ? C1 S2 C3 102.4(2) . . ? C4 C3 S2 114.3(3) . . ? C3 C4 S5 115.6(3) . . ? C6 S5 C4 102.1(2) . . ? C7 C6 S5 110.2(2) . . ? C8 C7 C12 118.9(3) . . ? C8 C7 C6 118.9(3) . . ? C12 C7 C6 122.2(3) . . ? C9 C8 C7 121.9(3) . . ? C8 C9 C10 119.7(3) . . ? C11 C10 C9 119.3(3) . . ? C10 C11 C12 121.7(3) . . ? C11 C12 C7 118.7(3) . . ? C11 C12 C13 119.6(3) . . ? C7 C12 C13 121.6(2) . . ? C12 C13 S14 108.0(2) . . ? C15 S14 C13 101.31(14) . . ? C16 C15 S14 113.0(2) . . ? C15 C16 S17 109.3(2) . . ? C18 S17 C16 99.28(13) . . ? C19 C18 S17 113.5(2) . . ? N24 C19 C20 122.6(3) . . ? N24 C19 C18 117.0(2) . . ? C20 C19 C18 120.4(3) . . ? C21 C20 C19 119.1(3) . . ? C20 C21 C22 118.8(3) . . ? C21 C22 C23 119.3(3) . . ? N24 C23 C22 122.0(3) . . ? N24 C23 C1 117.3(2) . . ? C22 C23 C1 120.6(3) . . ? C19 N24 C23 118.1(2) . . ? _refine_diff_density_max 0.461 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.049