# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_engle189_0m_a _database_code_depnum_ccdc_archive 'CCDC 1995204' loop_ _audit_author_name _audit_author_address Pdxinwang ;The scripps research institute and Nankai university United States of America ; _audit_update_record ; 2020-04-06 deposited with the CCDC. 2020-09-17 downloaded from the CCDC. ; _audit_creation_date 2019-05-24 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2014/7 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C24 H25 N3 O3 Pd S' _chemical_formula_sum 'C24 H25 N3 O3 Pd S' _chemical_formula_weight 541.93 _chemical_melting_point ? 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' Pd Pd -0.9988 1.0072 '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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2960(9) _cell_length_b 11.0174(14) _cell_length_c 12.5614(12) _cell_angle_alpha 111.695(3) _cell_angle_beta 91.745(3) _cell_angle_gamma 93.375(4) _cell_volume 1063.2(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5561 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.488 _cell_measurement_theta_min 2.463 _shelx_estimated_absorpt_T_max 0.951 _shelx_estimated_absorpt_T_min 0.766 _exptl_absorpt_coefficient_mu 1.004 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.7048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0645 before and 0.0303 after correction. The Ratio of minimum to maximum transmission is 0.9453. The \l/2 correction factor is Not present.' _exptl_absorpt_special_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11304 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.492 _diffrn_reflns_theta_min 1.748 _diffrn_ambient_temperature 100.0 _diffrn_detector 'Bruker APEX-II CCD' _diffrn_detector_area_resol_mean 8.258 _diffrn_detector_type 'CCD Area Detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'Kappa Four-Circle Diffractometer' _diffrn_measurement_device_type 'Bruker APEX II Ultra' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'Double Bounce Multilayer Mirrors' _diffrn_radiation_probe X-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Micro Focus Rotating Anode' _diffrn_source_type 'Bruker TXS' _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 4363 _reflns_number_total 4882 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'SAINT v8.38A (Bruker, 2017)' _computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)' _computing_data_reduction 'SAINT v8.38A (Bruker, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.829 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.135 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 4882 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0374 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+2.7918P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.1020 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C12(H12), C13(H13) 2.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C15(H15A,H15B), C11(H11A,H11B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C22(H22), C23(H23), C2(H2), C1(H1), C5(H5), C20(H20), C19(H19), C3(H3) 2.d Idealised Me refined as rotating group: C24(H24A,H24B,H24C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.25131(3) 0.32584(3) 0.71836(2) 0.01366(9) Uani 1 1 d . . . . . S1 S 0.57879(10) 0.49329(8) 0.76502(7) 0.01559(18) Uani 1 1 d . . . . . O2 O 0.5904(3) 0.4087(3) 0.8291(2) 0.0224(6) Uani 1 1 d . . . . . O3 O 0.6916(3) 0.4768(3) 0.6761(2) 0.0223(6) Uani 1 1 d . . . . . N1 N 0.1322(4) 0.1667(3) 0.7209(2) 0.0152(6) Uani 1 1 d . . . . . N3 N 0.3971(3) 0.4810(3) 0.7172(2) 0.0149(6) Uani 1 1 d . . . . . O1 O -0.0448(3) 0.0810(3) 0.8168(2) 0.0269(6) Uani 1 1 d . . . . . N2 N 0.3312(4) 0.1919(3) 0.5695(2) 0.0159(6) Uani 1 1 d . . . . . C9 C 0.2573(4) 0.0686(3) 0.5441(3) 0.0156(7) Uani 1 1 d . . . . . C6 C 0.1148(5) -0.1789(4) 0.5027(3) 0.0245(8) Uani 1 1 d . . . . . H6 H 0.0681 -0.2642 0.4903 0.029 Uiso 1 1 calc R . . . . C7 C 0.0815(5) -0.0732(3) 0.6039(3) 0.0197(7) Uani 1 1 d . . . . . H7 H 0.0106 -0.0878 0.6566 0.024 Uiso 1 1 calc R . . . . C22 C 0.7367(4) 0.8767(4) 0.9073(3) 0.0223(8) Uani 1 1 d . . . . . H22 H 0.7963 0.9383 0.8843 0.027 Uiso 1 1 calc R . . . . C18 C 0.6176(4) 0.6580(3) 0.8634(3) 0.0147(7) Uani 1 1 d . . . . . C23 C 0.7046(4) 0.7485(3) 0.8304(3) 0.0176(7) Uani 1 1 d . . . . . H23 H 0.7423 0.7228 0.7551 0.021 Uiso 1 1 calc R . . . . C4 C 0.2840(4) -0.0359(4) 0.4412(3) 0.0193(7) Uani 1 1 d . . . . . C8 C 0.1521(4) 0.0508(3) 0.6258(3) 0.0157(7) Uani 1 1 d . . . . . C14 C 0.1021(5) 0.6007(4) 0.8057(3) 0.0199(7) Uani 1 1 d . . . . . H14A H 0.2148 0.6308 0.8364 0.024 Uiso 1 1 calc R . . . . H14B H 0.0300 0.6598 0.8592 0.024 Uiso 1 1 calc R . . . . C16 C 0.1916(5) 0.5358(4) 0.5987(3) 0.0214(8) Uani 1 1 d . . . . . H16A H 0.1543 0.4418 0.5722 0.026 Uiso 1 1 calc R . . . . H16B H 0.1823 0.5628 0.5320 0.026 Uiso 1 1 calc R . . . . C2 C 0.4518(5) 0.1159(4) 0.3887(3) 0.0266(9) Uani 1 1 d . . . . . H2 H 0.5172 0.1354 0.3355 0.032 Uiso 1 1 calc R . . . . C1 C 0.4260(4) 0.2145(4) 0.4949(3) 0.0200(7) Uani 1 1 d . . . . . H1 H 0.4782 0.2995 0.5137 0.024 Uiso 1 1 calc R . . . . C17 C 0.3671(5) 0.5526(4) 0.6403(3) 0.0215(8) Uani 1 1 d . . . . . H17A H 0.4348 0.5200 0.5734 0.026 Uiso 1 1 calc R . . . . H17B H 0.3989 0.6469 0.6818 0.026 Uiso 1 1 calc R . . . . C5 C 0.2115(5) -0.1620(4) 0.4227(3) 0.0241(8) Uani 1 1 d . . . . . H5 H 0.2300 -0.2343 0.3551 0.029 Uiso 1 1 calc R . . . . C12 C 0.1357(4) 0.4169(4) 0.8800(3) 0.0184(7) Uani 1 1 d . . . . . H12 H 0.2058 0.4816 0.9446 0.022 Uiso 1 1 calc R . . . . C13 C 0.0665(4) 0.4644(4) 0.8040(3) 0.0193(7) Uani 1 1 d . . . . . H13 H -0.0475 0.4283 0.7780 0.023 Uiso 1 1 calc R . . . . C20 C 0.5933(5) 0.8244(4) 1.0485(3) 0.0257(8) Uani 1 1 d . . . . . H20 H 0.5545 0.8502 1.1234 0.031 Uiso 1 1 calc R . . . . C10 C 0.0376(4) 0.1721(4) 0.8090(3) 0.0187(7) Uani 1 1 d . . . . . C21 C 0.6823(5) 0.9155(4) 1.0175(3) 0.0229(8) Uani 1 1 d . . . . . C19 C 0.5595(4) 0.6953(4) 0.9718(3) 0.0209(8) Uani 1 1 d . . . . . H19 H 0.4975 0.6342 0.9939 0.025 Uiso 1 1 calc R . . . . C3 C 0.3827(5) -0.0071(4) 0.3626(3) 0.0251(8) Uani 1 1 d . . . . . H3 H 0.4007 -0.0740 0.2912 0.030 Uiso 1 1 calc R . . . . C15 C 0.0811(5) 0.6138(4) 0.6890(3) 0.0200(7) Uani 1 1 d . . . . . H15A H -0.0323 0.5858 0.6593 0.024 Uiso 1 1 calc R . . . . H15B H 0.1000 0.7075 0.7005 0.024 Uiso 1 1 calc R . . . . C11 C 0.0476(5) 0.3069(4) 0.9052(3) 0.0208(7) Uani 1 1 d . . . . . H11A H -0.0639 0.3309 0.9248 0.025 Uiso 1 1 calc R . . . . H11B H 0.1020 0.3003 0.9739 0.025 Uiso 1 1 calc R . . . . C24 C 0.7198(6) 1.0541(4) 1.1029(4) 0.0355(11) Uani 1 1 d . . . . . H24A H 0.7537 1.0519 1.1776 0.053 Uiso 1 1 calc GR . . . . H24B H 0.6229 1.1028 1.1107 0.053 Uiso 1 1 calc GR . . . . H24C H 0.8070 1.0973 1.0758 0.053 Uiso 1 1 calc GR . . . . 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 0.01581(14) 0.01075(14) 0.01376(14) 0.00379(9) 0.00265(9) -0.00005(9) S1 0.0142(4) 0.0099(4) 0.0222(4) 0.0056(3) 0.0010(3) -0.0003(3) O2 0.0204(13) 0.0163(13) 0.0353(15) 0.0157(12) -0.0028(11) 0.0013(10) O3 0.0213(13) 0.0160(13) 0.0266(14) 0.0038(11) 0.0085(11) 0.0026(10) N1 0.0203(15) 0.0119(14) 0.0140(13) 0.0060(11) -0.0008(11) -0.0005(11) N3 0.0141(14) 0.0111(14) 0.0202(14) 0.0071(11) -0.0009(11) 0.0002(11) O1 0.0297(15) 0.0261(15) 0.0282(15) 0.0144(12) 0.0067(12) -0.0048(12) N2 0.0174(14) 0.0125(14) 0.0173(14) 0.0048(11) 0.0018(11) 0.0029(11) C9 0.0163(16) 0.0146(17) 0.0170(16) 0.0072(13) -0.0038(13) 0.0040(13) C6 0.026(2) 0.0119(17) 0.033(2) 0.0069(15) -0.0129(16) 0.0006(15) C7 0.0216(18) 0.0149(17) 0.0247(18) 0.0107(15) -0.0057(14) -0.0015(14) C22 0.0178(18) 0.0161(18) 0.034(2) 0.0119(16) -0.0012(15) -0.0032(14) C18 0.0117(15) 0.0114(16) 0.0209(17) 0.0066(13) -0.0019(12) -0.0018(12) C23 0.0172(17) 0.0156(17) 0.0209(17) 0.0076(14) 0.0037(13) 0.0009(13) C4 0.0186(17) 0.0182(18) 0.0198(17) 0.0047(14) -0.0033(13) 0.0085(14) C8 0.0180(17) 0.0145(17) 0.0156(16) 0.0074(13) -0.0052(13) 0.0001(13) C14 0.0241(19) 0.0176(18) 0.0174(17) 0.0049(14) 0.0043(14) 0.0059(14) C16 0.031(2) 0.0173(18) 0.0171(17) 0.0076(14) 0.0004(15) 0.0041(15) C2 0.027(2) 0.035(2) 0.0212(19) 0.0128(17) 0.0068(15) 0.0095(17) C1 0.0193(18) 0.0204(18) 0.0223(18) 0.0096(15) 0.0036(14) 0.0032(14) C17 0.0234(19) 0.024(2) 0.0222(18) 0.0145(16) 0.0067(14) 0.0046(15) C5 0.025(2) 0.0154(18) 0.0253(19) 0.0003(15) -0.0074(15) 0.0079(15) C12 0.0223(18) 0.0155(17) 0.0146(16) 0.0019(13) 0.0056(13) 0.0028(14) C13 0.0175(17) 0.0202(18) 0.0173(17) 0.0028(14) 0.0067(13) 0.0041(14) C20 0.026(2) 0.032(2) 0.0160(17) 0.0049(16) 0.0010(15) 0.0058(17) C10 0.0198(18) 0.0222(19) 0.0171(17) 0.0109(15) -0.0022(13) 0.0024(14) C21 0.0188(18) 0.0162(18) 0.0268(19) 0.0006(15) -0.0086(15) 0.0018(14) C19 0.0191(18) 0.025(2) 0.0204(18) 0.0112(15) -0.0001(14) -0.0013(15) C3 0.0220(19) 0.029(2) 0.0198(18) 0.0024(16) 0.0011(14) 0.0108(16) C15 0.0245(19) 0.0183(18) 0.0201(18) 0.0100(15) 0.0020(14) 0.0042(15) C11 0.0212(18) 0.0235(19) 0.0192(17) 0.0090(15) 0.0065(14) 0.0045(15) C24 0.037(2) 0.016(2) 0.039(2) -0.0054(17) -0.0138(19) 0.0051(17) _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 1.972(3) . ? Pd1 N3 2.040(3) . ? Pd1 N2 2.065(3) . ? Pd1 C12 2.185(3) . ? Pd1 C13 2.236(4) . ? S1 O2 1.445(3) . ? S1 O3 1.445(3) . ? S1 N3 1.585(3) . ? S1 C18 1.781(3) . ? N1 C8 1.412(4) . ? N1 C10 1.361(5) . ? N3 C17 1.480(4) . ? O1 C10 1.217(5) . ? N2 C9 1.375(4) . ? N2 C1 1.324(5) . ? C9 C4 1.412(5) . ? C9 C8 1.427(5) . ? C6 H6 0.9500 . ? C6 C7 1.419(5) . ? C6 C5 1.363(6) . ? C7 H7 0.9500 . ? C7 C8 1.379(5) . ? C22 H22 0.9500 . ? C22 C23 1.389(5) . ? C22 C21 1.388(6) . ? C18 C23 1.388(5) . ? C18 C19 1.380(5) . ? C23 H23 0.9500 . ? C4 C5 1.414(5) . ? C4 C3 1.413(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C13 1.505(5) . ? C14 C15 1.531(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.509(5) . ? C16 C15 1.516(5) . ? C2 H2 0.9500 . ? C2 C1 1.407(5) . ? C2 C3 1.357(6) . ? C1 H1 0.9500 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C5 H5 0.9500 . ? C12 H12 1.0000 . ? C12 C13 1.373(5) . ? C12 C11 1.516(5) . ? C13 H13 1.0000 . ? C20 H20 0.9500 . ? C20 C21 1.387(6) . ? C20 C19 1.397(6) . ? C10 C11 1.525(5) . ? C21 C24 1.514(5) . ? C19 H19 0.9500 . ? C3 H3 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N3 173.73(12) . . ? N1 Pd1 N2 81.49(12) . . ? N1 Pd1 C12 82.26(13) . . ? N1 Pd1 C13 96.28(13) . . ? N3 Pd1 N2 95.61(12) . . ? N3 Pd1 C12 100.39(13) . . ? N3 Pd1 C13 89.10(13) . . ? N2 Pd1 C12 163.65(13) . . ? N2 Pd1 C13 148.56(13) . . ? C12 Pd1 C13 36.17(14) . . ? O2 S1 O3 116.66(16) . . ? O2 S1 N3 108.11(15) . . ? O2 S1 C18 107.77(16) . . ? O3 S1 N3 111.89(16) . . ? O3 S1 C18 105.70(16) . . ? N3 S1 C18 106.11(16) . . ? C8 N1 Pd1 115.2(2) . . ? C10 N1 Pd1 120.9(2) . . ? C10 N1 C8 123.9(3) . . ? S1 N3 Pd1 117.34(16) . . ? C17 N3 Pd1 123.8(2) . . ? C17 N3 S1 115.1(2) . . ? C9 N2 Pd1 111.8(2) . . ? C1 N2 Pd1 128.2(3) . . ? C1 N2 C9 119.6(3) . . ? N2 C9 C4 121.3(3) . . ? N2 C9 C8 117.3(3) . . ? C4 C9 C8 121.4(3) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C5 C6 C7 122.1(4) . . ? C6 C7 H7 120.0 . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 120.0 . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C21 C22 C23 120.5(3) . . ? C23 C18 S1 119.9(3) . . ? C19 C18 S1 119.7(3) . . ? C19 C18 C23 120.3(3) . . ? C22 C23 H23 120.0 . . ? C18 C23 C22 120.1(3) . . ? C18 C23 H23 120.0 . . ? C9 C4 C5 118.7(3) . . ? C9 C4 C3 117.3(3) . . ? C3 C4 C5 124.0(4) . . ? N1 C8 C9 114.1(3) . . ? C7 C8 N1 127.8(3) . . ? C7 C8 C9 118.2(3) . . ? H14A C14 H14B 107.5 . . ? C13 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C13 C14 C15 115.0(3) . . ? C15 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? H16A C16 H16B 107.7 . . ? C17 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C17 C16 C15 113.9(3) . . ? C15 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C3 C2 C1 119.7(4) . . ? N2 C1 C2 121.7(4) . . ? N2 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? N3 C17 C16 111.7(3) . . ? N3 C17 H17A 109.3 . . ? N3 C17 H17B 109.3 . . ? C16 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? Pd1 C12 H12 116.1 . . ? C13 C12 Pd1 73.9(2) . . ? C13 C12 H12 116.1 . . ? C13 C12 C11 120.0(3) . . ? C11 C12 Pd1 106.7(2) . . ? C11 C12 H12 116.1 . . ? Pd1 C13 H13 113.7 . . ? C14 C13 Pd1 113.7(2) . . ? C14 C13 H13 113.7 . . ? C12 C13 Pd1 69.9(2) . . ? C12 C13 C14 124.5(3) . . ? C12 C13 H13 113.7 . . ? C21 C20 H20 119.3 . . ? C21 C20 C19 121.4(4) . . ? C19 C20 H20 119.3 . . ? N1 C10 C11 113.3(3) . . ? O1 C10 N1 126.1(3) . . ? O1 C10 C11 120.6(3) . . ? C22 C21 C24 121.0(4) . . ? C20 C21 C22 118.6(3) . . ? C20 C21 C24 120.4(4) . . ? C18 C19 C20 119.0(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C4 C3 H3 119.9 . . ? C2 C3 C4 120.2(4) . . ? C2 C3 H3 119.9 . . ? C14 C15 H15A 108.5 . . ? C14 C15 H15B 108.5 . . ? C16 C15 C14 115.3(3) . . ? C16 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C12 C11 C10 116.0(3) . . ? C12 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? C10 C11 H11A 108.3 . . ? C10 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _shelx_res_file ; engle189_0m_a.res created by SHELXL-2014/7 TITL engle189_0m_a.res in P-1 REM Old TITL engle189_0m in P1 REM SHELXT solution in P-1 REM R1 0.067, Rweak 0.011, Alpha 0.121, Orientation as input REM Formula found by SHELXT: C25 N O4 Pd S CELL 0.71073 8.296 11.0174 12.5614 111.695 91.745 93.375 ZERR 2 0.0009 0.0014 0.0012 0.003 0.003 0.004 LATT 1 SFAC C H N O Pd S UNIT 48 50 6 6 2 2 L.S. 10 PLAN 20 SIZE 0.05 0.1 0.28 TEMP -173.15 BOND $H LIST 6 fmap 2 ACTA REM REM REM WGHT 0.048200 2.791800 FVAR 0.38003 PD1 5 0.251309 0.325842 0.718362 11.00000 0.01581 0.01075 = 0.01376 0.00379 0.00265 -0.00005 S1 6 0.578787 0.493286 0.765019 11.00000 0.01422 0.00995 = 0.02216 0.00565 0.00105 -0.00026 O2 4 0.590370 0.408654 0.829074 11.00000 0.02043 0.01635 = 0.03527 0.01568 -0.00278 0.00134 O3 4 0.691594 0.476776 0.676142 11.00000 0.02128 0.01596 = 0.02657 0.00377 0.00846 0.00256 N1 3 0.132184 0.166741 0.720940 11.00000 0.02027 0.01188 = 0.01398 0.00598 -0.00085 -0.00055 N3 3 0.397122 0.480951 0.717171 11.00000 0.01413 0.01111 = 0.02024 0.00707 -0.00088 0.00017 O1 4 -0.044785 0.081021 0.816829 11.00000 0.02968 0.02607 = 0.02819 0.01442 0.00667 -0.00477 N2 3 0.331157 0.191913 0.569488 11.00000 0.01742 0.01246 = 0.01730 0.00477 0.00175 0.00291 C9 1 0.257314 0.068631 0.544139 11.00000 0.01629 0.01462 = 0.01702 0.00716 -0.00377 0.00403 C6 1 0.114766 -0.178868 0.502687 11.00000 0.02637 0.01191 = 0.03290 0.00694 -0.01292 0.00055 AFIX 43 H6 2 0.068114 -0.264174 0.490263 11.00000 -1.20000 AFIX 0 C7 1 0.081511 -0.073168 0.603909 11.00000 0.02158 0.01487 = 0.02470 0.01074 -0.00572 -0.00152 AFIX 43 H7 2 0.010551 -0.087805 0.656621 11.00000 -1.20000 AFIX 0 C22 1 0.736652 0.876721 0.907301 11.00000 0.01780 0.01610 = 0.03447 0.01193 -0.00115 -0.00324 AFIX 43 H22 2 0.796252 0.938289 0.884277 11.00000 -1.20000 AFIX 0 C18 1 0.617613 0.658025 0.863368 11.00000 0.01167 0.01142 = 0.02088 0.00659 -0.00186 -0.00177 C23 1 0.704604 0.748527 0.830367 11.00000 0.01723 0.01555 = 0.02094 0.00758 0.00371 0.00092 AFIX 43 H23 2 0.742282 0.722798 0.755088 11.00000 -1.20000 AFIX 0 C4 1 0.284003 -0.035923 0.441166 11.00000 0.01858 0.01820 = 0.01979 0.00469 -0.00329 0.00850 C8 1 0.152122 0.050822 0.625845 11.00000 0.01797 0.01445 = 0.01561 0.00742 -0.00525 0.00012 C14 1 0.102082 0.600669 0.805701 11.00000 0.02410 0.01762 = 0.01736 0.00486 0.00435 0.00586 AFIX 23 H14A 2 0.214785 0.630801 0.836426 11.00000 -1.20000 H14B 2 0.030007 0.659775 0.859212 11.00000 -1.20000 AFIX 0 C16 1 0.191584 0.535832 0.598722 11.00000 0.03097 0.01733 = 0.01710 0.00760 0.00043 0.00410 AFIX 23 H16A 2 0.154314 0.441831 0.572204 11.00000 -1.20000 H16B 2 0.182301 0.562845 0.532001 11.00000 -1.20000 AFIX 0 C2 1 0.451779 0.115930 0.388676 11.00000 0.02708 0.03470 = 0.02120 0.01279 0.00678 0.00952 AFIX 43 H2 2 0.517249 0.135406 0.335451 11.00000 -1.20000 AFIX 0 C1 1 0.426047 0.214488 0.494942 11.00000 0.01929 0.02037 = 0.02227 0.00961 0.00360 0.00324 AFIX 43 H1 2 0.478153 0.299495 0.513697 11.00000 -1.20000 AFIX 0 C17 1 0.367050 0.552596 0.640257 11.00000 0.02341 0.02447 = 0.02224 0.01450 0.00665 0.00461 AFIX 23 H17A 2 0.434803 0.520019 0.573377 11.00000 -1.20000 H17B 2 0.398871 0.646909 0.681793 11.00000 -1.20000 AFIX 0 C5 1 0.211493 -0.161956 0.422698 11.00000 0.02539 0.01536 = 0.02534 0.00025 -0.00738 0.00795 AFIX 43 H5 2 0.230038 -0.234300 0.355063 11.00000 -1.20000 AFIX 0 C12 1 0.135660 0.416900 0.879972 11.00000 0.02230 0.01551 = 0.01462 0.00188 0.00564 0.00285 AFIX 13 H12 2 0.205840 0.481572 0.944568 11.00000 -1.20000 AFIX 0 C13 1 0.066501 0.464383 0.803973 11.00000 0.01749 0.02017 = 0.01735 0.00276 0.00673 0.00407 AFIX 13 H13 2 -0.047483 0.428278 0.777954 11.00000 -1.20000 AFIX 0 C20 1 0.593320 0.824364 1.048466 11.00000 0.02589 0.03211 = 0.01599 0.00487 0.00096 0.00583 AFIX 43 H20 2 0.554525 0.850219 1.123436 11.00000 -1.20000 AFIX 0 C10 1 0.037632 0.172099 0.809022 11.00000 0.01976 0.02219 = 0.01713 0.01090 -0.00220 0.00237 C21 1 0.682291 0.915540 1.017512 11.00000 0.01878 0.01617 = 0.02684 0.00056 -0.00864 0.00179 C19 1 0.559530 0.695314 0.971759 11.00000 0.01914 0.02501 = 0.02038 0.01121 -0.00007 -0.00128 AFIX 43 H19 2 0.497498 0.634155 0.993890 11.00000 -1.20000 AFIX 0 C3 1 0.382662 -0.007059 0.362561 11.00000 0.02202 0.02876 = 0.01982 0.00243 0.00108 0.01076 AFIX 43 H3 2 0.400661 -0.074004 0.291176 11.00000 -1.20000 AFIX 0 C15 1 0.081144 0.613826 0.688985 11.00000 0.02454 0.01828 = 0.02011 0.01003 0.00205 0.00419 AFIX 23 H15A 2 -0.032336 0.585824 0.659263 11.00000 -1.20000 H15B 2 0.099978 0.707505 0.700454 11.00000 -1.20000 AFIX 0 C11 1 0.047582 0.306867 0.905229 11.00000 0.02121 0.02351 = 0.01924 0.00900 0.00647 0.00451 AFIX 23 H11A 2 -0.063883 0.330923 0.924755 11.00000 -1.20000 H11B 2 0.101997 0.300301 0.973933 11.00000 -1.20000 AFIX 0 C24 1 0.719759 1.054105 1.102935 11.00000 0.03709 0.01581 = 0.03934 -0.00539 -0.01380 0.00507 AFIX 137 H24A 2 0.753668 1.051930 1.177588 11.00000 -1.50000 H24B 2 0.622887 1.102836 1.110743 11.00000 -1.50000 H24C 2 0.806980 1.097258 1.075780 11.00000 -1.50000 AFIX 0 HKLF 4 REM engle189_0m_a.res in P-1 REM R1 = 0.0374 for 4363 Fo > 4sig(Fo) and 0.0449 for all 4882 data REM 290 parameters refined using 0 restraints END WGHT 0.0482 2.7990 REM Highest difference peak 0.829, deepest hole -0.525, 1-sigma level 0.135 Q1 1 0.5182 0.5009 0.7972 11.00000 0.05 0.83 Q2 1 0.5059 0.4931 0.7494 11.00000 0.05 0.78 Q3 1 0.6130 0.5969 0.8406 11.00000 0.05 0.71 Q4 1 0.6086 0.4622 0.7033 11.00000 0.05 0.70 Q5 1 0.2188 0.0584 0.5960 11.00000 0.05 0.70 Q6 1 0.5547 0.4404 0.8810 11.00000 0.05 0.63 Q7 1 0.7104 0.8868 0.9561 11.00000 0.05 0.62 Q8 1 0.7096 0.8198 0.8681 11.00000 0.05 0.61 Q9 1 0.1804 0.3393 0.6610 11.00000 0.05 0.60 Q10 1 0.6438 0.6937 0.8435 11.00000 0.05 0.60 Q11 1 0.6152 0.6835 0.9188 11.00000 0.05 0.60 Q12 1 0.1402 0.3478 0.7126 11.00000 0.05 0.59 Q13 1 0.3334 0.4724 0.7424 11.00000 0.05 0.59 Q14 1 0.3203 0.3051 0.6366 11.00000 0.05 0.56 Q15 1 0.4048 0.1577 0.4445 11.00000 0.05 0.55 Q16 1 0.2658 0.0199 0.4967 11.00000 0.05 0.55 Q17 1 0.6952 0.9735 1.0662 11.00000 0.05 0.54 Q18 1 0.2682 0.6042 0.6381 11.00000 0.05 0.54 Q19 1 0.0523 0.5814 0.7198 11.00000 0.05 0.54 Q20 1 0.5877 0.7536 1.0096 11.00000 0.05 0.54 ; _shelx_res_checksum 23216 _olex2_submission_special_instructions 'No special instructions were received'