# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_jdp21c _database_code_depnum_ccdc_archive 'CCDC 875871' #TrackingRef 'JD2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 Cl N4 O Pd S' _chemical_formula_weight 491.24 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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 15.5491(14) _cell_length_b 7.6562(7) _cell_length_c 15.7781(14) _cell_angle_alpha 90.00 _cell_angle_beta 105.304(7) _cell_angle_gamma 90.00 _cell_volume 1811.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.300 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_T_max 0.732 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_reflns_number 26837 _diffrn_reflns_av_R_equivalents 0.1323 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.78 _reflns_number_total 4193 _reflns_number_gt 2550 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1865P)^2^+8.1677P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4193 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1101 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.2265 _refine_ls_wR_factor_gt 0.1765 _refine_ls_goodness_of_fit_ref 0.719 _refine_ls_restrained_S_all 0.719 _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 Pd1 Pd 0.33839(4) 0.39045(8) 0.37949(4) 0.0449(2) Uani 1 1 d . . . Cl1 Cl 0.85970(17) -0.0872(4) 0.64306(19) 0.0801(8) Uani 1 1 d . . . S1 S 0.33537(15) 0.3386(3) 0.23896(13) 0.0567(5) Uani 1 1 d . . . N2 N 0.4863(4) 0.1883(10) 0.3378(4) 0.0502(15) Uani 1 1 d . . . N1 N 0.4575(4) 0.2656(8) 0.4043(3) 0.0406(13) Uani 1 1 d . . . O2 O 0.1736(4) 0.5401(10) 0.2814(4) 0.0682(17) Uani 1 1 d . . . O1 O 0.3348(4) 0.4389(7) 0.5073(3) 0.0503(13) Uani 1 1 d . . . C1 C 0.4316(5) 0.2132(11) 0.2596(5) 0.0479(18) Uani 1 1 d . . . C2 C 0.5071(5) 0.2444(10) 0.4834(5) 0.0483(17) Uani 1 1 d . . . H2 H 0.4846 0.2951 0.5267 0.058 Uiso 1 1 calc R . . C3 C 0.5921(5) 0.1548(10) 0.5165(5) 0.0484(18) Uani 1 1 d . . . C4 C 0.6276(6) 0.1503(12) 0.6080(5) 0.055(2) Uani 1 1 d . . . H4 H 0.5948 0.1992 0.6435 0.066 Uiso 1 1 calc R . . C5 C 0.7089(6) 0.0766(11) 0.6471(6) 0.055(2) Uani 1 1 d . . . H5 H 0.7311 0.0768 0.7079 0.066 Uiso 1 1 calc R . . C6 C 0.7572(5) 0.0016(12) 0.5940(6) 0.059(2) Uani 1 1 d . . . C7 C 0.7233(6) -0.0008(13) 0.5054(6) 0.064(2) Uani 1 1 d . . . H7 H 0.7556 -0.0532 0.4704 0.077 Uiso 1 1 calc R . . C8 C 0.6418(6) 0.0731(12) 0.4666(5) 0.057(2) Uani 1 1 d . . . H8 H 0.6196 0.0684 0.4058 0.069 Uiso 1 1 calc R . . N3 N 0.4537(5) 0.1374(11) 0.1911(4) 0.068(2) Uani 1 1 d . . . H9A H 0.5016 0.0763 0.1998 0.081 Uiso 1 1 calc R . . H9B H 0.4198 0.1501 0.1388 0.081 Uiso 1 1 calc R . . N4 N 0.2200(5) 0.5077(9) 0.3563(4) 0.0542(16) Uani 1 1 d . . . C9 C 0.1940(5) 0.5525(10) 0.4291(5) 0.0470(17) Uani 1 1 d . . . C10 C 0.2612(6) 0.5129(11) 0.5088(5) 0.0533(19) Uani 1 1 d . . . C11 C 0.2451(7) 0.5650(14) 0.5903(6) 0.072(3) Uani 1 1 d . . . H13 H 0.2882 0.5465 0.6430 0.086 Uiso 1 1 calc R . . C12 C 0.1681(8) 0.6401(15) 0.5899(7) 0.081(3) Uani 1 1 d . . . H14 H 0.1592 0.6727 0.6437 0.097 Uiso 1 1 calc R . . C13 C 0.0977(6) 0.6745(14) 0.5126(6) 0.068(2) Uani 1 1 d . . . C18 C 0.1095(6) 0.6301(10) 0.4304(6) 0.056(2) Uani 1 1 d . . . C17 C 0.0382(6) 0.6647(14) 0.3564(7) 0.073(3) Uani 1 1 d . . . H17 H 0.0430 0.6350 0.3007 0.088 Uiso 1 1 calc R . . C14 C 0.0208(7) 0.7510(17) 0.5208(7) 0.089(3) Uani 1 1 d . . . H14A H 0.0149 0.7807 0.5762 0.106 Uiso 1 1 calc R . . C16 C -0.0381(7) 0.7416(16) 0.3658(8) 0.088(3) Uani 1 1 d . . . H16 H -0.0841 0.7654 0.3160 0.105 Uiso 1 1 calc R . . C15 C -0.0483(8) 0.7843(17) 0.4468(8) 0.093(4) Uani 1 1 d . . . H15 H -0.1010 0.8350 0.4521 0.112 Uiso 1 1 calc R . . 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 Pd1 0.0558(4) 0.0384(4) 0.0421(4) -0.0011(2) 0.0157(2) -0.0024(3) Cl1 0.0635(14) 0.0768(18) 0.0922(18) 0.0197(14) 0.0068(12) 0.0041(12) S1 0.0687(13) 0.0618(13) 0.0409(10) 0.0029(9) 0.0166(9) 0.0072(11) N2 0.053(4) 0.061(4) 0.040(3) 0.004(3) 0.018(3) 0.000(3) N1 0.058(3) 0.033(3) 0.031(3) 0.000(2) 0.013(2) -0.007(3) O2 0.066(4) 0.086(5) 0.046(3) 0.003(3) 0.003(3) 0.017(3) O1 0.060(3) 0.051(3) 0.041(3) -0.004(2) 0.016(2) 0.013(3) C1 0.061(5) 0.050(5) 0.038(4) 0.004(3) 0.022(3) -0.005(4) C2 0.064(5) 0.041(4) 0.045(4) 0.002(3) 0.023(3) -0.006(4) C3 0.059(5) 0.042(4) 0.043(4) 0.000(3) 0.011(3) -0.006(4) C4 0.066(5) 0.052(5) 0.047(4) -0.005(4) 0.017(4) -0.015(4) C5 0.063(5) 0.049(5) 0.049(4) 0.008(4) 0.007(4) -0.008(4) C6 0.050(4) 0.057(6) 0.065(5) 0.018(4) 0.006(4) -0.004(4) C7 0.067(5) 0.062(6) 0.064(5) -0.004(5) 0.020(4) 0.001(5) C8 0.055(5) 0.068(6) 0.048(4) 0.000(4) 0.013(4) 0.002(4) N3 0.070(5) 0.099(7) 0.039(3) -0.005(4) 0.023(3) 0.012(4) N4 0.068(4) 0.045(4) 0.047(4) 0.001(3) 0.011(3) 0.001(3) C9 0.056(4) 0.038(4) 0.048(4) 0.001(3) 0.015(3) 0.002(3) C10 0.070(5) 0.043(5) 0.048(4) -0.001(3) 0.017(4) 0.001(4) C11 0.092(7) 0.081(7) 0.045(4) 0.007(4) 0.023(4) 0.026(6) C12 0.092(7) 0.094(8) 0.065(6) 0.001(5) 0.036(5) 0.031(6) C13 0.071(6) 0.066(6) 0.072(6) -0.010(5) 0.026(5) 0.014(5) C18 0.067(5) 0.034(4) 0.066(5) 0.002(4) 0.019(4) 0.000(4) C17 0.066(6) 0.079(7) 0.069(6) -0.008(5) 0.006(4) 0.018(5) C14 0.080(7) 0.104(10) 0.088(7) 0.003(7) 0.033(6) 0.030(7) C16 0.067(6) 0.093(9) 0.092(7) -0.006(7) 0.002(5) 0.016(6) C15 0.079(7) 0.090(9) 0.115(9) -0.005(8) 0.035(7) 0.022(7) _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 Pd1 N4 1.993(7) . ? Pd1 N1 2.028(6) . ? Pd1 O1 2.065(5) . ? Pd1 S1 2.241(2) . ? Cl1 C6 1.718(8) . ? S1 C1 1.734(8) . ? N2 C1 1.314(9) . ? N2 N1 1.379(8) . ? N1 C2 1.293(9) . ? O2 N4 1.236(8) . ? O1 C10 1.283(9) . ? C1 N3 1.349(9) . ? C2 C3 1.458(11) . ? C2 H2 0.9300 . ? C3 C8 1.390(12) . ? C3 C4 1.404(10) . ? C4 C5 1.373(13) . ? C4 H4 0.9300 . ? C5 C6 1.388(13) . ? C5 H5 0.9300 . ? C6 C7 1.359(12) . ? C7 C8 1.374(12) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? N3 H9A 0.8600 . ? N3 H9B 0.8600 . ? N4 C9 1.360(10) . ? C9 C10 1.439(11) . ? C9 C18 1.447(11) . ? C10 C11 1.431(11) . ? C11 C12 1.327(14) . ? C11 H13 0.9300 . ? C12 C13 1.432(14) . ? C12 H14 0.9300 . ? C13 C14 1.369(13) . ? C13 C18 1.398(13) . ? C18 C17 1.407(13) . ? C17 C16 1.368(14) . ? C17 H17 0.9300 . ? C14 C15 1.386(15) . ? C14 H14A 0.9300 . ? C16 C15 1.368(14) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? 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 N4 Pd1 N1 178.5(2) . . ? N4 Pd1 O1 80.6(2) . . ? N1 Pd1 O1 98.9(2) . . ? N4 Pd1 S1 96.93(19) . . ? N1 Pd1 S1 83.52(16) . . ? O1 Pd1 S1 177.34(16) . . ? C1 S1 Pd1 96.9(2) . . ? C1 N2 N1 113.0(6) . . ? C2 N1 N2 116.8(6) . . ? C2 N1 Pd1 121.8(5) . . ? N2 N1 Pd1 121.3(4) . . ? C10 O1 Pd1 110.6(5) . . ? N2 C1 N3 116.8(7) . . ? N2 C1 S1 124.7(6) . . ? N3 C1 S1 118.5(6) . . ? N1 C2 C3 131.1(7) . . ? N1 C2 H2 114.4 . . ? C3 C2 H2 114.4 . . ? C8 C3 C4 116.4(8) . . ? C8 C3 C2 126.6(7) . . ? C4 C3 C2 116.9(7) . . ? C5 C4 C3 122.5(9) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? C4 C5 C6 118.7(8) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 120.1(8) . . ? C7 C6 Cl1 121.4(8) . . ? C5 C6 Cl1 118.5(7) . . ? C6 C7 C8 121.0(9) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C3 121.3(8) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? C1 N3 H9A 120.0 . . ? C1 N3 H9B 120.0 . . ? H9A N3 H9B 120.0 . . ? O2 N4 C9 121.9(7) . . ? O2 N4 Pd1 123.0(5) . . ? C9 N4 Pd1 115.1(5) . . ? N4 C9 C10 112.1(7) . . ? N4 C9 C18 126.1(7) . . ? C10 C9 C18 121.8(7) . . ? O1 C10 C11 120.6(7) . . ? O1 C10 C9 121.5(7) . . ? C11 C10 C9 117.9(8) . . ? C12 C11 C10 119.2(9) . . ? C12 C11 H13 120.4 . . ? C10 C11 H13 120.4 . . ? C11 C12 C13 124.7(9) . . ? C11 C12 H14 117.6 . . ? C13 C12 H14 117.6 . . ? C14 C13 C18 121.6(10) . . ? C14 C13 C12 119.2(9) . . ? C18 C13 C12 119.2(8) . . ? C13 C18 C17 117.1(8) . . ? C13 C18 C9 117.1(8) . . ? C17 C18 C9 125.8(8) . . ? C16 C17 C18 120.5(10) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C14 C15 120.0(10) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C17 C16 C15 121.4(10) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C15 C14 119.3(10) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.78 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.198 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.109 data_jd3 _database_code_depnum_ccdc_archive 'CCDC 875872' #TrackingRef 'JD3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 Cl N4 O Pd S' _chemical_formula_weight 463.23 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' Pd Pd -0.9988 1.0072 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 14.643(2) _cell_length_b 7.9232(11) _cell_length_c 15.771(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.518(10) _cell_angle_gamma 90.00 _cell_volume 1744.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 1.349 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.721 _exptl_absorpt_correction_T_max 0.733 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_reflns_number 20164 _diffrn_reflns_av_R_equivalents 0.1211 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.99 _reflns_number_total 4079 _reflns_number_gt 2315 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4079 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1925 _refine_ls_R_factor_gt 0.1257 _refine_ls_wR_factor_ref 0.3160 _refine_ls_wR_factor_gt 0.2886 _refine_ls_goodness_of_fit_ref 1.688 _refine_ls_restrained_S_all 1.688 _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 Pd1 Pd 0.65982(8) 0.88681(12) 0.96460(6) 0.0430(4) Uani 1 1 d . . . S1 S 0.6610(3) 0.8406(5) 0.8250(2) 0.0532(10) Uani 1 1 d . . . N2 N 0.5063(8) 0.6789(14) 0.8432(6) 0.043(3) Uani 1 1 d . . . N1 N 0.5357(8) 0.7575(13) 0.9247(6) 0.042(2) Uani 1 1 d . . . N3 N 0.5402(10) 0.6349(16) 0.7119(7) 0.065(4) Uani 1 1 d . . . H3A H 0.4895 0.5739 0.6936 0.078 Uiso 1 1 calc R . . H3B H 0.5761 0.6506 0.6783 0.078 Uiso 1 1 calc R . . N4 N 0.7856(8) 1.0144(14) 1.0059(7) 0.048(3) Uani 1 1 d . . . C2 C 0.4851(9) 0.7360(15) 0.9766(8) 0.041(3) Uani 1 1 d . . . H2 H 0.5105 0.7830 1.0328 0.050 Uiso 1 1 calc R . . C1 C 0.5639(10) 0.7074(16) 0.7950(7) 0.043(3) Uani 1 1 d . . . C17 C 0.8091(13) 1.0495(19) 1.0949(10) 0.061(4) Uani 1 1 d . . . C12 C 0.8951(13) 1.134(2) 1.1387(13) 0.071(5) Uani 1 1 d . . . C10 C 0.9263(13) 1.144(2) 1.0000(14) 0.080(5) Uani 1 1 d . . . H10 H 0.9645 1.1792 0.9658 0.096 Uiso 1 1 calc R . . C9 C 0.8417(13) 1.060(2) 0.9585(12) 0.075(5) Uani 1 1 d . . . H9 H 0.8247 1.0360 0.8980 0.091 Uiso 1 1 calc R . . C16 C 0.7435(11) 0.9982(18) 1.1406(10) 0.057(4) Uani 1 1 d . . . C11 C 0.9553(15) 1.175(3) 1.0870(17) 0.095(6) Uani 1 1 d . . . H11 H 1.0149 1.2241 1.1133 0.115 Uiso 1 1 calc R . . C15 C 0.7677(18) 1.028(3) 1.2255(13) 0.120(10) Uani 1 1 d . . . H15 H 0.7279 0.9919 1.2580 0.144 Uiso 1 1 calc R . . C13 C 0.9172(19) 1.158(3) 1.2302(15) 0.118(9) Uani 1 1 d . . . H13 H 0.9757 1.2032 1.2631 0.142 Uiso 1 1 calc R . . O1 O 0.6639(7) 0.9239(12) 1.0959(6) 0.052(2) Uani 1 1 d . . . C8 C 0.3585(9) 0.6430(14) 1.0374(7) 0.038(3) Uani 1 1 d . . . H8 H 0.3925 0.6981 1.0893 0.045 Uiso 1 1 calc R . . C4 C 0.3391(11) 0.569(2) 0.8846(10) 0.064(4) Uani 1 1 d . . . H4 H 0.3598 0.5689 0.8343 0.076 Uiso 1 1 calc R . . C3 C 0.3933(10) 0.6492(15) 0.9625(8) 0.043(3) Uani 1 1 d . . . C6 C 0.2243(10) 0.4909(17) 0.9554(11) 0.051(4) Uani 1 1 d . . . C7 C 0.2775(11) 0.560(2) 1.0354(10) 0.057(4) Uani 1 1 d . . . H7 H 0.2582 0.5487 1.0862 0.069 Uiso 1 1 calc R . . C5 C 0.2550(12) 0.490(2) 0.8831(11) 0.068(5) Uani 1 1 d . . . H5 H 0.2190 0.4355 0.8317 0.082 Uiso 1 1 calc R . . C14 C 0.8512(19) 1.113(3) 1.2688(13) 0.117(9) Uani 1 1 d . . . H14 H 0.8621 1.1409 1.3283 0.140 Uiso 1 1 calc R . . Cl1 Cl 0.1161(4) 0.3897(6) 0.9514(4) 0.0904(16) 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 Pd1 0.0649(8) 0.0349(6) 0.0353(5) 0.0007(4) 0.0244(5) -0.0027(5) S1 0.065(2) 0.065(2) 0.0349(17) -0.0038(15) 0.0244(16) -0.0135(18) N2 0.070(8) 0.035(6) 0.029(5) -0.010(4) 0.022(5) 0.000(5) N1 0.062(7) 0.034(6) 0.038(5) -0.003(4) 0.026(5) -0.008(5) N3 0.092(10) 0.078(10) 0.035(6) -0.012(6) 0.035(6) -0.017(7) N4 0.065(8) 0.044(7) 0.040(6) 0.001(5) 0.021(5) 0.004(6) C2 0.064(8) 0.036(7) 0.029(6) -0.004(5) 0.021(6) 0.002(6) C1 0.073(9) 0.034(7) 0.025(6) 0.004(5) 0.021(6) -0.004(6) C17 0.097(13) 0.035(8) 0.051(9) 0.005(7) 0.020(8) 0.005(8) C12 0.064(11) 0.060(11) 0.086(13) 0.000(9) 0.016(9) -0.015(9) C10 0.054(11) 0.081(14) 0.101(15) -0.006(11) 0.019(10) -0.010(9) C9 0.075(13) 0.079(12) 0.074(12) 0.015(9) 0.025(10) -0.007(10) C16 0.078(11) 0.041(8) 0.055(9) -0.004(7) 0.023(8) -0.006(8) C11 0.067(13) 0.081(14) 0.13(2) 0.006(14) 0.022(13) -0.020(11) C15 0.17(2) 0.14(2) 0.079(13) -0.043(13) 0.085(15) -0.093(19) C13 0.123(19) 0.120(19) 0.078(15) 0.002(12) -0.021(13) -0.076(16) O1 0.054(6) 0.068(7) 0.040(5) -0.012(4) 0.025(4) -0.023(5) C8 0.061(9) 0.027(7) 0.029(6) -0.002(4) 0.018(6) -0.009(5) C4 0.066(10) 0.081(12) 0.056(9) -0.007(8) 0.036(8) -0.017(9) C3 0.064(9) 0.030(7) 0.040(7) -0.006(5) 0.023(6) -0.007(6) C6 0.047(8) 0.029(7) 0.082(11) 0.004(7) 0.025(8) -0.004(6) C7 0.059(10) 0.058(9) 0.060(9) 0.026(7) 0.024(8) -0.004(7) C5 0.079(12) 0.067(11) 0.067(10) -0.022(8) 0.034(9) -0.026(9) C14 0.14(2) 0.15(2) 0.053(11) -0.036(13) 0.025(13) -0.056(18) Cl1 0.066(3) 0.071(3) 0.140(5) 0.010(3) 0.041(3) -0.012(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 Pd1 N1 2.015(10) . ? Pd1 N4 2.030(12) . ? Pd1 O1 2.074(8) . ? Pd1 S1 2.236(3) . ? S1 C1 1.719(14) . ? N2 C1 1.315(15) . ? N2 N1 1.375(13) . ? N1 C2 1.270(14) . ? N3 C1 1.375(15) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 C9 1.316(18) . ? N4 C17 1.368(17) . ? C2 C3 1.467(18) . ? C2 H2 0.9300 . ? C17 C12 1.41(2) . ? C17 C16 1.42(2) . ? C12 C13 1.39(3) . ? C12 C11 1.41(3) . ? C10 C11 1.33(3) . ? C10 C9 1.38(2) . ? C10 H10 0.9300 . ? C9 H9 0.9300 . ? C16 C15 1.30(2) . ? C16 O1 1.307(17) . ? C11 H11 0.9300 . ? C15 C14 1.38(3) . ? C15 H15 0.9300 . ? C13 C14 1.34(3) . ? C13 H13 0.9300 . ? C8 C7 1.350(19) . ? C8 C3 1.420(16) . ? C8 H8 0.9300 . ? C4 C5 1.38(2) . ? C4 C3 1.40(2) . ? C4 H4 0.9300 . ? C6 C5 1.345(19) . ? C6 C7 1.38(2) . ? C6 Cl1 1.760(14) . ? C7 H7 0.9300 . ? C5 H5 0.9300 . ? C14 H14 0.9300 . ? 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 N1 Pd1 N4 179.2(4) . . ? N1 Pd1 O1 97.8(4) . . ? N4 Pd1 O1 81.9(4) . . ? N1 Pd1 S1 83.3(3) . . ? N4 Pd1 S1 97.0(3) . . ? O1 Pd1 S1 177.7(3) . . ? C1 S1 Pd1 97.0(4) . . ? C1 N2 N1 112.8(11) . . ? C2 N1 N2 117.5(11) . . ? C2 N1 Pd1 120.9(9) . . ? N2 N1 Pd1 121.5(7) . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C9 N4 C17 121.3(15) . . ? C9 N4 Pd1 127.9(11) . . ? C17 N4 Pd1 110.7(10) . . ? N1 C2 C3 130.7(11) . . ? N1 C2 H2 114.7 . . ? C3 C2 H2 114.7 . . ? N2 C1 N3 117.2(12) . . ? N2 C1 S1 124.6(9) . . ? N3 C1 S1 118.0(9) . . ? N4 C17 C12 120.7(15) . . ? N4 C17 C16 117.5(15) . . ? C12 C17 C16 121.7(15) . . ? C13 C12 C17 117.9(17) . . ? C13 C12 C11 125(2) . . ? C17 C12 C11 116.6(18) . . ? C11 C10 C9 122.7(19) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? N4 C9 C10 119.0(17) . . ? N4 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C15 C16 O1 124.2(15) . . ? C15 C16 C17 116.9(16) . . ? O1 C16 C17 118.9(13) . . ? C10 C11 C12 119.4(19) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C16 C15 C14 121.6(17) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C14 C13 C12 117.5(18) . . ? C14 C13 H13 121.3 . . ? C12 C13 H13 121.3 . . ? C16 O1 Pd1 110.9(8) . . ? C7 C8 C3 122.1(12) . . ? C7 C8 H8 119.0 . . ? C3 C8 H8 119.0 . . ? C5 C4 C3 119.3(13) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C3 C8 117.7(12) . . ? C4 C3 C2 126.6(11) . . ? C8 C3 C2 115.7(11) . . ? C5 C6 C7 122.5(13) . . ? C5 C6 Cl1 119.6(12) . . ? C7 C6 Cl1 117.7(11) . . ? C8 C7 C6 117.6(13) . . ? C8 C7 H7 121.2 . . ? C6 C7 H7 121.2 . . ? C6 C5 C4 120.6(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C13 C14 C15 123.9(19) . . ? C13 C14 H14 118.0 . . ? C15 C14 H14 118.0 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 6.379 _refine_diff_density_min -1.454 _refine_diff_density_rms 0.319 data_jd111 _database_code_depnum_ccdc_archive 'CCDC 875873' #TrackingRef 'jd111.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N4 O Pd S' _chemical_formula_weight 445.83 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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 27.9696(19) _cell_length_b 35.857(3) _cell_length_c 7.0330(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7053.4(9) _cell_formula_units_Z 16 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3600 _exptl_absorpt_coefficient_mu 1.185 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_correction_T_max 0.847 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_reflns_number 25241 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -51 _diffrn_reflns_limit_k_max 51 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.64 _reflns_number_total 4785 _reflns_number_gt 3269 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0376P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(4) _refine_ls_number_reflns 4785 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.933 _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 Pd1 Pd -0.001107(10) 0.151547(7) 0.42627(10) 0.04149(9) Uani 1 1 d . . . S1 S -0.07325(4) 0.12858(3) 0.35637(17) 0.0541(3) Uani 1 1 d . . . O1 O 0.06376(10) 0.17611(8) 0.4892(5) 0.0555(8) Uani 1 1 d . . . N2 N -0.04391(11) 0.09361(9) 0.6758(6) 0.0499(8) Uani 1 1 d . . . N1 N -0.00617(11) 0.11801(9) 0.6541(6) 0.0448(8) Uani 1 1 d . . . N3 N -0.11403(13) 0.07432(10) 0.5477(6) 0.0648(12) Uani 1 1 d . . . H3A H -0.1166 0.0582 0.6375 0.078 Uiso 1 1 calc R . . H3B H -0.1358 0.0759 0.4618 0.078 Uiso 1 1 calc R . . N4 N 0.00525(10) 0.18304(9) 0.1903(5) 0.0453(8) Uani 1 1 d . . . C1 C -0.07600(15) 0.09712(11) 0.5417(7) 0.0453(11) Uani 1 1 d . . . C2 C 0.02708(15) 0.11679(11) 0.7814(7) 0.0498(10) Uani 1 1 d . . . H2 H 0.0529 0.1324 0.7568 0.060 Uiso 1 1 calc R . . C3 C 0.03155(15) 0.09542(10) 0.9563(7) 0.0477(10) Uani 1 1 d . . . C4 C 0.07192(19) 0.10334(13) 1.0677(7) 0.0634(14) Uani 1 1 d . . . H4 H 0.0939 0.1210 1.0259 0.076 Uiso 1 1 calc R . . C5 C 0.07942(18) 0.08531(15) 1.2381(8) 0.0700(15) Uani 1 1 d . . . H5 H 0.1064 0.0912 1.3095 0.084 Uiso 1 1 calc R . . C6 C 0.04851(18) 0.05914(13) 1.3049(7) 0.0590(12) Uani 1 1 d . . . C7 C 0.00822(17) 0.05142(13) 1.1970(7) 0.0619(13) Uani 1 1 d . . . H7 H -0.0138 0.0340 1.2414 0.074 Uiso 1 1 calc R . . C8 C -0.00005(16) 0.06901(13) 1.0244(7) 0.0569(12) Uani 1 1 d . . . H8 H -0.0271 0.0630 0.9539 0.068 Uiso 1 1 calc R . . C9 C 0.0553(2) 0.03942(14) 1.4931(8) 0.0890(19) Uani 1 1 d . . . H9A H 0.0795 0.0521 1.5657 0.133 Uiso 1 1 calc R . . H9B H 0.0651 0.0141 1.4707 0.133 Uiso 1 1 calc R . . H9C H 0.0258 0.0395 1.5624 0.133 Uiso 1 1 calc R . . C10 C -0.02352(16) 0.18474(12) 0.0420(7) 0.0550(12) Uani 1 1 d . . . H10 H -0.0511 0.1703 0.0406 0.066 Uiso 1 1 calc R . . C11 C -0.01358(17) 0.20767(13) -0.1124(8) 0.0645(14) Uani 1 1 d . . . H11 H -0.0342 0.2082 -0.2161 0.077 Uiso 1 1 calc R . . C12 C 0.02631(18) 0.22937(12) -0.1116(8) 0.0645(14) Uani 1 1 d . . . H12 H 0.0328 0.2449 -0.2143 0.077 Uiso 1 1 calc R . . C13 C 0.05744(15) 0.22832(11) 0.0432(7) 0.0525(11) Uani 1 1 d . . . C14 C 0.09959(19) 0.24993(12) 0.0576(9) 0.0645(14) Uani 1 1 d . . . H14 H 0.1075 0.2669 -0.0374 0.077 Uiso 1 1 calc R . . C15 C 0.1285(2) 0.24562(14) 0.2119(10) 0.0742(19) Uani 1 1 d . . . H15 H 0.1563 0.2598 0.2202 0.089 Uiso 1 1 calc R . . C16 C 0.11790(16) 0.22107(13) 0.3553(9) 0.0687(14) Uani 1 1 d . . . H16 H 0.1392 0.2187 0.4561 0.082 Uiso 1 1 calc R . . C17 C 0.07648(14) 0.19955(11) 0.3556(8) 0.0494(10) Uani 1 1 d . . . C18 C 0.04634(13) 0.20406(10) 0.1924(7) 0.0443(9) 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 Pd1 0.03607(15) 0.04465(13) 0.04374(15) 0.0032(2) -0.00901(12) -0.00067(15) S1 0.0414(6) 0.0648(6) 0.0562(7) 0.0169(5) -0.0183(5) -0.0067(5) O1 0.0472(17) 0.0636(17) 0.056(2) 0.0043(15) -0.0138(15) -0.0093(13) N2 0.0405(18) 0.0590(19) 0.050(2) 0.0142(19) -0.015(2) -0.0043(15) N1 0.0400(18) 0.0488(19) 0.046(2) 0.0028(16) -0.0109(16) -0.0003(14) N3 0.046(2) 0.078(3) 0.070(3) 0.029(2) -0.025(2) -0.0152(18) N4 0.0405(18) 0.0439(18) 0.052(2) 0.0028(16) -0.0051(19) 0.0026(13) C1 0.036(2) 0.054(2) 0.046(3) 0.003(2) -0.0023(19) 0.0012(18) C2 0.039(2) 0.053(2) 0.058(3) -0.003(2) -0.013(2) -0.0054(18) C3 0.045(2) 0.051(2) 0.047(3) -0.007(2) -0.018(2) 0.0080(18) C4 0.050(3) 0.084(3) 0.057(3) -0.008(3) -0.018(3) 0.000(2) C5 0.058(3) 0.090(4) 0.063(4) -0.007(3) -0.030(3) 0.019(3) C6 0.065(3) 0.069(3) 0.043(3) -0.002(2) -0.017(2) 0.025(2) C7 0.073(3) 0.061(3) 0.052(3) 0.009(2) -0.014(3) 0.009(2) C8 0.055(3) 0.067(3) 0.049(3) 0.003(2) -0.017(2) 0.003(2) C9 0.117(5) 0.085(3) 0.065(4) 0.006(3) -0.043(3) 0.032(3) C10 0.047(3) 0.059(3) 0.060(3) 0.012(2) -0.014(2) 0.002(2) C11 0.066(3) 0.067(3) 0.060(4) 0.011(3) -0.012(3) 0.012(2) C12 0.065(3) 0.057(3) 0.072(4) 0.012(3) 0.011(3) 0.013(2) C13 0.051(3) 0.046(2) 0.061(3) -0.002(2) 0.013(2) 0.0113(19) C14 0.060(3) 0.058(3) 0.076(4) 0.000(3) 0.028(3) -0.005(2) C15 0.056(3) 0.079(3) 0.088(6) -0.005(3) 0.021(3) -0.019(3) C16 0.045(3) 0.079(3) 0.083(4) -0.002(3) -0.003(3) -0.015(2) C17 0.038(2) 0.049(2) 0.061(3) -0.007(2) -0.002(2) 0.0007(18) C18 0.034(2) 0.0435(18) 0.055(3) -0.001(2) 0.006(2) 0.0030(15) _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 Pd1 N1 2.008(4) . ? Pd1 N4 2.015(4) . ? Pd1 O1 2.065(3) . ? Pd1 S1 2.2343(11) . ? S1 C1 1.725(4) . ? O1 C17 1.310(5) . ? N2 C1 1.308(5) . ? N2 N1 1.379(4) . ? N1 C2 1.292(5) . ? N3 C1 1.342(5) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 C10 1.319(5) . ? N4 C18 1.374(4) . ? C2 C3 1.454(6) . ? C2 H2 0.9300 . ? C3 C8 1.381(6) . ? C3 C4 1.403(6) . ? C4 C5 1.378(7) . ? C4 H4 0.9300 . ? C5 C6 1.360(7) . ? C5 H5 0.9300 . ? C6 C7 1.386(6) . ? C6 C9 1.513(6) . ? C7 C8 1.388(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.390(7) . ? C10 H10 0.9300 . ? C11 C12 1.360(7) . ? C11 H11 0.9300 . ? C12 C13 1.395(7) . ? C12 H12 0.9300 . ? C13 C18 1.397(6) . ? C13 C14 1.414(6) . ? C14 C15 1.362(8) . ? C14 H14 0.9300 . ? C15 C16 1.371(8) . ? C15 H15 0.9300 . ? C16 C17 1.392(6) . ? C16 H16 0.9300 . ? C17 C18 1.433(6) . ? 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 N1 Pd1 N4 177.16(14) . . ? N1 Pd1 O1 98.42(13) . . ? N4 Pd1 O1 81.94(12) . . ? N1 Pd1 S1 83.75(9) . . ? N4 Pd1 S1 96.03(10) . . ? O1 Pd1 S1 176.38(8) . . ? C1 S1 Pd1 96.61(15) . . ? C17 O1 Pd1 111.0(3) . . ? C1 N2 N1 112.6(4) . . ? C2 N1 N2 116.9(4) . . ? C2 N1 Pd1 121.5(3) . . ? N2 N1 Pd1 121.5(3) . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C10 N4 C18 119.5(4) . . ? C10 N4 Pd1 128.6(3) . . ? C18 N4 Pd1 111.9(3) . . ? N2 C1 N3 117.6(4) . . ? N2 C1 S1 125.2(3) . . ? N3 C1 S1 117.2(3) . . ? N1 C2 C3 131.8(4) . . ? N1 C2 H2 114.1 . . ? C3 C2 H2 114.1 . . ? C8 C3 C4 117.4(4) . . ? C8 C3 C2 126.8(4) . . ? C4 C3 C2 115.8(4) . . ? C5 C4 C3 120.9(5) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 121.8(5) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C7 117.8(4) . . ? C5 C6 C9 123.0(5) . . ? C7 C6 C9 119.2(5) . . ? C6 C7 C8 121.6(5) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C3 C8 C7 120.5(4) . . ? C3 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C10 C11 121.6(4) . . ? N4 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 120.0(5) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.0(5) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C18 117.7(4) . . ? C12 C13 C14 124.1(5) . . ? C18 C13 C14 118.2(5) . . ? C15 C14 C13 119.3(5) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 122.1(5) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C15 C16 C17 122.4(6) . . ? C15 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? O1 C17 C16 125.6(5) . . ? O1 C17 C18 119.2(3) . . ? C16 C17 C18 115.2(5) . . ? N4 C18 C13 121.3(4) . . ? N4 C18 C17 116.0(4) . . ? C13 C18 C17 122.7(4) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 30.64 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.298 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.071