# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name J.Brown _publ_contact_author_name J.Brown _publ_contact_author_email john.brown@chem.ox.ac.uk _publ_section_title ; Anilide Activation of Adjacent C-H Bonds in the Palladium-catalysed Fujiwara-Moritani Reaction ; # Attachment '- CrystallographicData.cif' #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 775340' #TrackingRef '- CrystallographicData.cif' #============================================================================== # Diffractometer details _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; # General computing _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The NH hydrogen atom was located in a difference Fourier map and its coordinates and isotropic displacement parameter subsequently refined. Other hydrogen atoms were positioned geometrically, the preferred orientations of the methyl groups having been previously determined by examination of the Fourier map. ; #============================================================= _cell_length_a 7.7689(3) _cell_angle_alpha 90.718(2) _cell_length_b 9.4176(5) _cell_angle_beta 107.538(2) _cell_length_c 10.9474(6) _cell_angle_gamma 114.239(2) _cell_volume 687.80(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'Pd ' -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986 5.2659 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C13 H16 N2 O3 Pd1 ' _chemical_formula_moiety ' C13 H16 N2 O3 Pd1 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 354.68 _cell_measurement_reflns_used 8763 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.14 _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 1.354 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.96 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 8763 _reflns_number_total 3102 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_theta_min 5.103 _diffrn_reflns_theta_max 27.479 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.479 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.88 _refine_diff_density_max 1.48 _refine_ls_number_reflns 2614 _refine_ls_number_restraints 0 _refine_ls_number_parameters 176 #_refine_ls_R_factor_ref 0.0392 _refine_ls_wR_factor_ref 0.0457 _refine_ls_goodness_of_fit_ref 1.0710 #_reflns_number_all 3102 _refine_ls_R_factor_all 0.0498 _refine_ls_wR_factor_all 0.0530 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2614 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_gt 0.0457 _refine_ls_shift/su_max 0.002776 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.21 0.598 0.783 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type Pd1 Pd 0.31808(4) 0.31284(3) 0.23481(3) 0.0285 1.0000 Uani C1 C 0.3989(5) 0.5393(4) 0.2812(3) 0.0276 1.0000 Uani C2 C 0.4920(5) 0.6498(5) 0.2095(4) 0.0300 1.0000 Uani C3 C 0.5519(6) 0.8109(5) 0.2401(4) 0.0335 1.0000 Uani C4 C 0.5194(6) 0.8636(5) 0.3480(4) 0.0382 1.0000 Uani C5 C 0.4271(6) 0.7571(5) 0.4197(4) 0.0371 1.0000 Uani C6 C 0.3626(5) 0.5952(5) 0.3853(4) 0.0295 1.0000 Uani N1 N 0.2602(5) 0.4956(4) 0.4611(3) 0.0327 1.0000 Uani C7 C 0.1509(6) 0.3419(5) 0.4344(4) 0.0317 1.0000 Uani O1 O 0.1307(4) 0.2547(4) 0.3373(3) 0.0350 1.0000 Uani C8 C 0.6487(7) 0.9281(5) 0.1599(5) 0.0438 1.0000 Uani C9 C 0.0448(6) 0.2623(6) 0.5259(4) 0.0393 1.0000 Uani O2 O 0.5088(4) 0.3538(3) 0.1328(3) 0.0315 1.0000 Uani C10 C 0.6797(6) 0.3575(4) 0.1948(4) 0.0291 1.0000 Uani O3 O 0.7419(5) 0.3554(5) 0.3128(3) 0.0484 1.0000 Uani C11 C 0.8066(6) 0.3597(5) 0.1136(4) 0.0343 1.0000 Uani N2 N 0.2067(6) 0.0646(4) 0.1792(4) 0.0378 1.0000 Uani C12 C 0.1226(6) -0.0694(5) 0.1547(4) 0.0358 1.0000 Uani C13 C 0.0117(7) -0.2406(5) 0.1242(5) 0.0433 1.0000 Uani H1 H 0.256(8) 0.531(6) 0.525(6) 0.039(13) 1.0000 Uiso H21 H 0.5164 0.6116 0.1336 0.0357 1.0000 Uiso H41 H 0.5634 0.9787 0.3729 0.0444 1.0000 Uiso H51 H 0.4060 0.7959 0.4969 0.0435 1.0000 Uiso H81 H 0.6604 0.8710 0.0874 0.0518 1.0000 Uiso H82 H 0.7851 1.0065 0.2160 0.0518 1.0000 Uiso H83 H 0.5643 0.9842 0.1233 0.0518 1.0000 Uiso H91 H 0.0721 0.3431 0.5981 0.0499 1.0000 Uiso H92 H 0.0944 0.1840 0.5624 0.0499 1.0000 Uiso H93 H -0.1027 0.2069 0.4782 0.0499 1.0000 Uiso H111 H 0.9361 0.3625 0.1705 0.0434 1.0000 Uiso H112 H 0.8345 0.4552 0.0698 0.0434 1.0000 Uiso H113 H 0.7335 0.2627 0.0466 0.0434 1.0000 Uiso H131 H -0.0803 -0.2783 0.1761 0.0522 1.0000 Uiso H132 H 0.1079 -0.2890 0.1461 0.0522 1.0000 Uiso H133 H -0.0686 -0.2718 0.0297 0.0522 1.0000 Uiso 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 0.02753(15) 0.03293(16) 0.02649(15) 0.00167(10) 0.00889(10) 0.01481(11) C1 0.0212(15) 0.0332(18) 0.0262(16) 0.0006(13) 0.0029(13) 0.0134(14) C2 0.0259(16) 0.0362(19) 0.0271(17) -0.0016(14) 0.0052(13) 0.0155(15) C3 0.0263(17) 0.0339(19) 0.0356(19) 0.0008(15) 0.0058(15) 0.0120(15) C4 0.0297(18) 0.036(2) 0.045(2) -0.0050(17) 0.0093(17) 0.0134(16) C5 0.0298(18) 0.046(2) 0.0334(19) -0.0058(16) 0.0059(15) 0.0176(17) C6 0.0228(16) 0.0377(19) 0.0266(17) 0.0003(14) 0.0047(13) 0.0144(14) N1 0.0312(16) 0.0471(19) 0.0227(15) -0.0002(13) 0.0089(12) 0.0201(15) C7 0.0265(17) 0.046(2) 0.0272(17) 0.0053(15) 0.0069(14) 0.0216(16) O1 0.0290(13) 0.0431(15) 0.0334(14) 0.0032(11) 0.0116(11) 0.0155(12) C8 0.040(2) 0.037(2) 0.052(3) 0.0096(19) 0.016(2) 0.0144(18) C9 0.0333(19) 0.057(3) 0.035(2) 0.0146(18) 0.0174(17) 0.0216(19) O2 0.0332(13) 0.0404(15) 0.0268(12) 0.0046(11) 0.0110(11) 0.0209(12) C10 0.0295(17) 0.0274(16) 0.0297(17) -0.0006(13) 0.0090(14) 0.0123(14) O3 0.0455(17) 0.086(3) 0.0280(14) 0.0060(15) 0.0108(13) 0.0429(18) C11 0.0363(19) 0.0364(19) 0.0360(19) 0.0090(15) 0.0180(16) 0.0170(16) N2 0.0383(18) 0.0408(19) 0.0382(18) 0.0028(14) 0.0159(15) 0.0189(16) C12 0.038(2) 0.039(2) 0.035(2) 0.0032(16) 0.0164(17) 0.0180(18) C13 0.050(2) 0.031(2) 0.049(2) 0.0047(17) 0.021(2) 0.0151(18) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Pd1 . C1 . 1.970(4) yes Pd1 . O1 . 2.006(3) yes Pd1 . O2 . 2.032(3) yes Pd1 . N2 . 2.138(4) yes C1 . C2 . 1.402(6) yes C1 . C6 . 1.398(5) yes C2 . C3 . 1.394(5) yes C2 . H21 . 1.000 no C3 . C4 . 1.404(6) yes C3 . C8 . 1.515(6) yes C4 . C5 . 1.380(7) yes C4 . H41 . 1.000 no C5 . C6 . 1.402(6) yes C5 . H51 . 1.000 no C6 . N1 . 1.417(5) yes N1 . C7 . 1.316(6) yes N1 . H1 . 0.78(6) no C7 . O1 . 1.264(5) yes C7 . C9 . 1.502(5) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C8 . H83 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no O2 . C10 . 1.281(5) yes C10 . O3 . 1.239(5) yes C10 . C11 . 1.509(5) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no N2 . C12 . 1.140(6) yes C12 . C13 . 1.458(6) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Pd1 . O1 . 91.62(14) yes C1 . Pd1 . O2 . 92.85(14) yes O1 . Pd1 . O2 . 175.12(12) yes C1 . Pd1 . N2 . 175.55(14) yes O1 . Pd1 . N2 . 85.74(13) yes O2 . Pd1 . N2 . 89.92(13) yes Pd1 . C1 . C2 . 121.1(3) yes Pd1 . C1 . C6 . 121.2(3) yes C2 . C1 . C6 . 117.7(3) yes C1 . C2 . C3 . 122.5(4) yes C1 . C2 . H21 . 118.729 no C3 . C2 . H21 . 118.729 no C2 . C3 . C4 . 118.3(4) yes C2 . C3 . C8 . 121.7(4) yes C4 . C3 . C8 . 120.0(4) yes C3 . C4 . C5 . 120.3(4) yes C3 . C4 . H41 . 119.826 no C5 . C4 . H41 . 119.826 no C4 . C5 . C6 . 120.5(4) yes C4 . C5 . H51 . 119.726 no C6 . C5 . H51 . 119.726 no C1 . C6 . C5 . 120.5(4) yes C1 . C6 . N1 . 123.5(4) yes C5 . C6 . N1 . 116.0(3) yes C6 . N1 . C7 . 127.9(3) yes C6 . N1 . H1 . 121(4) no C7 . N1 . H1 . 111(4) no N1 . C7 . O1 . 124.6(4) yes N1 . C7 . C9 . 118.4(4) yes O1 . C7 . C9 . 117.0(4) yes Pd1 . O1 . C7 . 124.8(3) yes C3 . C8 . H81 . 109.467 no C3 . C8 . H82 . 109.467 no H81 . C8 . H82 . 109.476 no C3 . C8 . H83 . 109.467 no H81 . C8 . H83 . 109.476 no H82 . C8 . H83 . 109.476 no C7 . C9 . H91 . 109.467 no C7 . C9 . H92 . 109.467 no H91 . C9 . H92 . 109.476 no C7 . C9 . H93 . 109.467 no H91 . C9 . H93 . 109.476 no H92 . C9 . H93 . 109.476 no Pd1 . O2 . C10 . 115.8(2) yes O2 . C10 . O3 . 124.8(4) yes O2 . C10 . C11 . 115.6(3) yes O3 . C10 . C11 . 119.6(3) yes C10 . C11 . H111 . 109.467 no C10 . C11 . H112 . 109.467 no H111 . C11 . H112 . 109.476 no C10 . C11 . H113 . 109.467 no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no Pd1 . N2 . C12 . 169.4(3) yes N2 . C12 . C13 . 178.8(4) yes C12 . C13 . H131 . 109.467 no C12 . C13 . H132 . 109.467 no H131 . C13 . H132 . 109.476 no C12 . C13 . H133 . 109.467 no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_site_symmetry_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag N1 H1 O3 2_666 0.78(6) 2.06(6) 2.837(5) 175(5) yes #============================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 775341' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 08-02-08 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5701 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 6.8157(1) _cell_length_b 11.0016(2) _cell_length_c 17.1316(4) _cell_angle_alpha 81.8338(7) _cell_angle_beta 89.2894(7) _cell_angle_gamma 76.2647(10) _cell_volume 1234.90(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986 5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C19 H22 N1 O4 Pd1 S1 # Dc = 1.26 Fooo = 594.00 Mu = 8.54 M = 466.85 # Found Formula = C23 H32 N3 O5.50 Pd1 S1 # Dc = 1.55 FOOO = 594.00 Mu = 8.77 M = 576.99 _chemical_formula_sum 'C23 H32 N3 O5.50 Pd1 S1' _chemical_formula_moiety 'C13 H16 N3 O Pd, C10 H15 O4 S, 0.5(H2 O)' _chemical_compound_source . _chemical_formula_weight 576.99 _cell_measurement_reflns_used 4721 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.19 _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 594 _exptl_absorpt_coefficient_mu 0.877 # Sheldrick geometric approximatio 0.85 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.93 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 15821 _reflns_number_total 5594 _diffrn_reflns_av_R_equivalents 0.035 # Number of reflections with Friedels Law is 5594 # Number of reflections without Friedels Law is 9396 # Theoretical number of reflections is about 5668 _diffrn_reflns_theta_min 5.154 _diffrn_reflns_theta_max 27.490 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.390 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -14 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.30 _oxford_diffrn_Wilson_scale 7.69 _atom_sites_solution_primary heavy #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.00 _refine_diff_density_max 1.06 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 5594 _refine_ls_number_restraints 0 _refine_ls_number_parameters 307 _oxford_refine_ls_R_factor_ref 0.0553 _refine_ls_wR_factor_ref 0.0953 _refine_ls_goodness_of_fit_ref 0.9423 _refine_ls_shift/su_max 0.000918 # The values computed from all data _oxford_reflns_number_all 5594 _refine_ls_R_factor_all 0.0553 _refine_ls_wR_factor_all 0.0953 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4673 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_gt 0.0887 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 2.38P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Pd1 Pd 0.96202(3) 0.55366(2) 0.607750(14) 0.0255 1.0000 Uani . . . . . . . O2 O 1.2497(3) 0.4841(2) 0.58357(13) 0.0301 1.0000 Uani . . . . . . . C3 C 1.3690(5) 0.3832(3) 0.61488(19) 0.0269 1.0000 Uani . . . . . . . N4 N 1.3261(4) 0.3100(2) 0.67709(16) 0.0295 1.0000 Uani . . . . . . . C5 C 1.1449(5) 0.3243(3) 0.72022(19) 0.0283 1.0000 Uani . . . . . . . C6 C 0.9725(5) 0.4217(3) 0.70061(18) 0.0268 1.0000 Uani . . . . . . . C7 C 0.8068(5) 0.4213(3) 0.7495(2) 0.0319 1.0000 Uani . . . . . . . C8 C 0.8057(5) 0.3285(3) 0.8137(2) 0.0344 1.0000 Uani . . . . . . . C9 C 0.6200(6) 0.3319(4) 0.8625(2) 0.0469 1.0000 Uani . . . . . . . C10 C 0.9796(5) 0.2325(3) 0.8305(2) 0.0367 1.0000 Uani . . . . . . . C11 C 1.1467(5) 0.2308(3) 0.7842(2) 0.0360 1.0000 Uani . . . . . . . C12 C 1.5702(5) 0.3426(3) 0.5791(2) 0.0313 1.0000 Uani . . . . . . . N13 N 0.6742(4) 0.6346(3) 0.62350(16) 0.0311 1.0000 Uani . . . . . . . C14 C 0.5114(5) 0.6866(3) 0.6322(2) 0.0335 1.0000 Uani . . . . . . . C15 C 0.3042(5) 0.7488(4) 0.6471(3) 0.0457 1.0000 Uani . . . . . . . N16 N 0.9557(4) 0.7002(2) 0.51003(16) 0.0306 1.0000 Uani . . . . . . . C17 C 0.9466(5) 0.7856(3) 0.4633(2) 0.0329 1.0000 Uani . . . . . . . C18 C 0.9390(7) 0.8941(4) 0.4028(3) 0.0530 1.0000 Uani . . . . . . . S19 S 0.62180(15) 0.98030(8) 0.70609(6) 0.0463 1.0000 Uani . . . . . . . O20 O 0.6473(4) 1.0992(2) 0.72790(17) 0.0466 1.0000 Uani . . . . . . . O21 O 0.6675(7) 0.9710(4) 0.6230(2) 0.0917 1.0000 Uani . . . . . . . O22 O 0.4291(4) 0.9563(3) 0.7289(2) 0.0704 1.0000 Uani . . . . . . . C23 C 0.8152(5) 0.8587(3) 0.7581(2) 0.0347 1.0000 Uani . . . . . . . C24 C 0.7780(5) 0.8175(3) 0.8449(2) 0.0386 1.0000 Uani . . . . . . . C25 C 0.6614(5) 0.7134(3) 0.8576(2) 0.0340 1.0000 Uani . . . . . . . O26 O 0.5606(4) 0.6820(2) 0.80973(15) 0.0406 1.0000 Uani . . . . . . . C27 C 0.7004(6) 0.6539(4) 0.9425(2) 0.0415 1.0000 Uani . . . . . . . C28 C 0.8426(6) 0.7275(4) 0.9725(2) 0.0482 1.0000 Uani . . . . . . . C29 C 0.9641(6) 0.7553(4) 0.8996(2) 0.0432 1.0000 Uani . . . . . . . C30 C 1.0992(6) 0.8463(4) 0.9096(3) 0.0537 1.0000 Uani . . . . . . . C31 C 1.0911(6) 0.6345(4) 0.8725(3) 0.0525 1.0000 Uani . . . . . . . C32 C 0.7071(7) 0.8619(4) 0.9803(3) 0.0552 1.0000 Uani . . . . . . . C33 C 0.6596(6) 0.9211(4) 0.8957(2) 0.0456 1.0000 Uani . . . . . . . O34 O 0.5711(12) 1.0911(6) 0.4871(3) 0.0739 0.5000 Uani . . . . . . . H71 H 0.6905 0.4870 0.7381 0.0367 1.0000 Uiso R . . . . . . H92 H 0.6553 0.3209 0.9174 0.0702 1.0000 Uiso R . . . . . . H93 H 0.5228 0.4113 0.8490 0.0703 1.0000 Uiso R . . . . . . H91 H 0.5586 0.2651 0.8531 0.0704 1.0000 Uiso R . . . . . . H101 H 0.9840 0.1688 0.8737 0.0419 1.0000 Uiso R . . . . . . H111 H 1.2621 0.1659 0.7962 0.0409 1.0000 Uiso R . . . . . . H123 H 1.6673 0.3001 0.6197 0.0464 1.0000 Uiso R . . . . . . H121 H 1.6114 0.4144 0.5518 0.0466 1.0000 Uiso R . . . . . . H122 H 1.5633 0.2848 0.5432 0.0467 1.0000 Uiso R . . . . . . H152 H 0.2439 0.7938 0.5978 0.0680 1.0000 Uiso R . . . . . . H153 H 0.3046 0.8083 0.6834 0.0679 1.0000 Uiso R . . . . . . H151 H 0.2296 0.6869 0.6679 0.0685 1.0000 Uiso R . . . . . . H182 H 0.8022 0.9441 0.3959 0.0765 1.0000 Uiso R . . . . . . H181 H 1.0245 0.9446 0.4181 0.0761 1.0000 Uiso R . . . . . . H183 H 0.9842 0.8663 0.3536 0.0763 1.0000 Uiso R . . . . . . H231 H 0.9355 0.8911 0.7547 0.0400 1.0000 Uiso R . . . . . . H232 H 0.8348 0.7864 0.7297 0.0401 1.0000 Uiso R . . . . . . H271 H 0.5746 0.6651 0.9714 0.0493 1.0000 Uiso R . . . . . . H272 H 0.7637 0.5645 0.9455 0.0492 1.0000 Uiso R . . . . . . H281 H 0.9246 0.6847 1.0197 0.0541 1.0000 Uiso R . . . . . . H302 H 1.2001 0.8078 0.9506 0.0821 1.0000 Uiso R . . . . . . H301 H 1.0178 0.9234 0.9242 0.0818 1.0000 Uiso R . . . . . . H303 H 1.1645 0.8663 0.8605 0.0819 1.0000 Uiso R . . . . . . H311 H 1.1862 0.5906 0.9141 0.0711 1.0000 Uiso R . . . . . . H313 H 1.1580 0.6592 0.8244 0.0711 1.0000 Uiso R . . . . . . H312 H 1.0039 0.5818 0.8613 0.0711 1.0000 Uiso R . . . . . . H322 H 0.7802 0.9111 1.0074 0.0651 1.0000 Uiso R . . . . . . H321 H 0.5828 0.8557 1.0088 0.0653 1.0000 Uiso R . . . . . . H332 H 0.7014 0.9998 0.8848 0.0520 1.0000 Uiso R . . . . . . H331 H 0.5150 0.9391 0.8853 0.0520 1.0000 Uiso R . . . . . . H41 H 1.4211 0.2446 0.6934 0.0354 1.0000 Uiso R . . . . . . H341 H 0.5974 1.0443 0.5295 0.1182 0.5000 Uiso R . . . . . . H342 H 0.5080 1.0706 0.4524 0.1180 0.5000 Uiso 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 0.02646(13) 0.02166(13) 0.02676(14) -0.00154(9) -0.00106(9) -0.00366(8) O2 0.0279(11) 0.0248(11) 0.0343(13) 0.0023(9) 0.0007(9) -0.0037(8) C3 0.0304(16) 0.0221(14) 0.0284(16) -0.0040(12) -0.0036(12) -0.0058(12) N4 0.0288(14) 0.0259(13) 0.0296(14) 0.0035(11) -0.0023(11) -0.0024(10) C5 0.0325(16) 0.0267(15) 0.0258(16) -0.0021(12) -0.0015(12) -0.0081(12) C6 0.0326(16) 0.0263(15) 0.0238(16) -0.0053(12) -0.0007(12) -0.0102(12) C7 0.0353(17) 0.0285(16) 0.0311(18) -0.0047(13) 0.0018(13) -0.0063(13) C8 0.0425(19) 0.0361(18) 0.0285(18) -0.0059(14) 0.0036(14) -0.0165(14) C9 0.050(2) 0.051(2) 0.040(2) -0.0005(17) 0.0121(17) -0.0177(18) C10 0.047(2) 0.0357(18) 0.0267(17) 0.0035(14) -0.0011(15) -0.0142(15) C11 0.0379(18) 0.0334(18) 0.0320(18) 0.0052(14) -0.0023(14) -0.0050(14) C12 0.0313(17) 0.0262(16) 0.0334(18) -0.0021(13) -0.0008(13) -0.0022(12) N13 0.0336(15) 0.0305(14) 0.0283(15) -0.0032(11) -0.0022(11) -0.0065(11) C14 0.0347(19) 0.0328(17) 0.0331(18) -0.0088(14) -0.0034(14) -0.0055(14) C15 0.0274(18) 0.052(2) 0.058(3) -0.0245(19) -0.0060(16) 0.0003(15) N16 0.0294(14) 0.0255(14) 0.0340(15) -0.0023(12) -0.0023(11) -0.0020(10) C17 0.0284(16) 0.0274(17) 0.040(2) -0.0036(15) -0.0071(14) -0.0014(12) C18 0.059(3) 0.038(2) 0.054(3) 0.0176(18) -0.017(2) -0.0079(18) S19 0.0510(6) 0.0295(4) 0.0533(6) -0.0019(4) -0.0289(5) -0.0007(4) O20 0.0469(15) 0.0259(12) 0.0629(18) 0.0007(12) -0.0170(13) -0.0038(10) O21 0.145(4) 0.080(2) 0.0409(19) -0.0099(17) -0.043(2) -0.004(2) O22 0.0395(16) 0.0378(15) 0.132(3) -0.0157(17) -0.0350(18) -0.0021(12) C23 0.0289(17) 0.0308(17) 0.041(2) -0.0021(14) 0.0000(14) -0.0025(13) C24 0.0358(18) 0.0377(19) 0.040(2) 0.0012(15) -0.0047(15) -0.0085(14) C25 0.0273(16) 0.0327(17) 0.041(2) -0.0058(15) -0.0011(14) -0.0050(13) O26 0.0348(13) 0.0413(14) 0.0474(16) -0.0099(12) -0.0003(11) -0.0103(10) C27 0.040(2) 0.042(2) 0.041(2) 0.0007(16) 0.0040(16) -0.0108(15) C28 0.052(2) 0.050(2) 0.040(2) 0.0062(17) -0.0109(17) -0.0116(18) C29 0.0368(19) 0.045(2) 0.046(2) -0.0028(17) -0.0041(16) -0.0084(16) C30 0.044(2) 0.061(3) 0.060(3) -0.002(2) -0.0127(19) -0.0218(19) C31 0.0326(19) 0.040(2) 0.079(3) -0.008(2) 0.0069(19) 0.0019(15) C32 0.053(2) 0.062(3) 0.051(3) -0.020(2) 0.0027(19) -0.007(2) C33 0.0342(19) 0.038(2) 0.062(3) -0.0107(18) 0.0018(17) -0.0005(15) O34 0.129(6) 0.071(4) 0.033(3) 0.004(3) -0.018(4) -0.053(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3570(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Pd1 . O2 . 1.990(2) yes Pd1 . C6 . 1.985(3) yes Pd1 . N13 . 1.985(3) yes Pd1 . N16 . 2.146(3) yes O2 . C3 . 1.263(4) yes C3 . N4 . 1.315(4) yes C3 . C12 . 1.490(4) yes N4 . C5 . 1.419(4) yes N4 . H41 . 0.861 no C5 . C6 . 1.397(4) yes C5 . C11 . 1.390(4) yes C6 . C7 . 1.398(4) yes C7 . C8 . 1.392(5) yes C7 . H71 . 0.938 no C8 . C9 . 1.504(5) yes C8 . C10 . 1.390(5) yes C9 . H92 . 0.957 no C9 . H93 . 0.963 no C9 . H91 . 0.960 no C10 . C11 . 1.379(5) yes C10 . H101 . 0.939 no C11 . H111 . 0.931 no C12 . H123 . 0.955 no C12 . H121 . 0.959 no C12 . H122 . 0.955 no N13 . C14 . 1.140(4) yes C14 . C15 . 1.452(5) yes C15 . H152 . 0.960 no C15 . H153 . 0.965 no C15 . H151 . 0.970 no N16 . C17 . 1.134(4) yes C17 . C18 . 1.457(5) yes C18 . H182 . 0.962 no C18 . H181 . 0.957 no C18 . H183 . 0.959 no S19 . O20 . 1.460(3) yes S19 . O21 . 1.466(4) yes S19 . O22 . 1.438(3) yes S19 . C23 . 1.781(3) yes C23 . C24 . 1.529(5) yes C23 . H231 . 0.967 no C23 . H232 . 0.971 no C24 . C25 . 1.532(5) yes C24 . C29 . 1.546(5) yes C24 . C33 . 1.593(5) yes C25 . O26 . 1.213(4) yes C25 . C27 . 1.506(5) yes C27 . C28 . 1.537(5) yes C27 . H271 . 0.976 no C27 . H272 . 0.970 no C28 . C29 . 1.525(6) yes C28 . C32 . 1.569(6) yes C28 . H281 . 0.984 no C29 . C30 . 1.540(5) yes C29 . C31 . 1.533(5) yes C30 . H302 . 0.966 no C30 . H301 . 0.960 no C30 . H303 . 0.969 no C31 . H311 . 0.964 no C31 . H313 . 0.973 no C31 . H312 . 0.961 no C32 . C33 . 1.507(6) yes C32 . H322 . 0.981 no C32 . H321 . 0.984 no C33 . H332 . 0.967 no C33 . H331 . 0.972 no O34 . H341 . 0.823 no O34 . H342 . 0.824 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . Pd1 . C6 . 92.11(11) yes O2 . Pd1 . N13 . 174.91(10) yes C6 . Pd1 . N13 . 92.98(12) yes O2 . Pd1 . N16 . 87.58(9) yes C6 . Pd1 . N16 . 177.85(11) yes N13 . Pd1 . N16 . 87.33(10) yes Pd1 . O2 . C3 . 128.8(2) yes O2 . C3 . N4 . 124.0(3) yes O2 . C3 . C12 . 118.6(3) yes N4 . C3 . C12 . 117.4(3) yes C3 . N4 . C5 . 128.7(3) yes C3 . N4 . H41 . 115.1 no C5 . N4 . H41 . 116.2 no N4 . C5 . C6 . 124.1(3) yes N4 . C5 . C11 . 115.0(3) yes C6 . C5 . C11 . 120.8(3) yes C5 . C6 . Pd1 . 121.9(2) yes C5 . C6 . C7 . 116.6(3) yes Pd1 . C6 . C7 . 121.5(2) yes C6 . C7 . C8 . 123.4(3) yes C6 . C7 . H71 . 118.1 no C8 . C7 . H71 . 118.5 no C7 . C8 . C9 . 120.6(3) yes C7 . C8 . C10 . 118.1(3) yes C9 . C8 . C10 . 121.3(3) yes C8 . C9 . H92 . 110.0 no C8 . C9 . H93 . 110.6 no H92 . C9 . H93 . 109.1 no C8 . C9 . H91 . 110.1 no H92 . C9 . H91 . 108.7 no H93 . C9 . H91 . 108.4 no C8 . C10 . C11 . 120.1(3) yes C8 . C10 . H101 . 120.2 no C11 . C10 . H101 . 119.7 no C5 . C11 . C10 . 121.0(3) yes C5 . C11 . H111 . 120.0 no C10 . C11 . H111 . 119.0 no C3 . C12 . H123 . 109.3 no C3 . C12 . H121 . 110.4 no H123 . C12 . H121 . 109.6 no C3 . C12 . H122 . 109.7 no H123 . C12 . H122 . 108.2 no H121 . C12 . H122 . 109.6 no Pd1 . N13 . C14 . 176.7(3) yes N13 . C14 . C15 . 177.2(4) yes C14 . C15 . H152 . 107.6 no C14 . C15 . H153 . 109.0 no H152 . C15 . H153 . 109.2 no C14 . C15 . H151 . 110.4 no H152 . C15 . H151 . 109.5 no H153 . C15 . H151 . 111.0 no Pd1 . N16 . C17 . 173.5(3) yes N16 . C17 . C18 . 178.8(4) yes C17 . C18 . H182 . 109.4 no C17 . C18 . H181 . 109.8 no H182 . C18 . H181 . 109.5 no C17 . C18 . H183 . 110.2 no H182 . C18 . H183 . 109.0 no H181 . C18 . H183 . 108.8 no O20 . S19 . O21 . 111.7(2) yes O20 . S19 . O22 . 112.21(18) yes O21 . S19 . O22 . 113.9(2) yes O20 . S19 . C23 . 106.35(16) yes O21 . S19 . C23 . 103.6(2) yes O22 . S19 . C23 . 108.46(18) yes S19 . C23 . C24 . 116.6(2) yes S19 . C23 . H231 . 105.8 no C24 . C23 . H231 . 108.6 no S19 . C23 . H232 . 106.9 no C24 . C23 . H232 . 109.4 no H231 . C23 . H232 . 109.4 no C23 . C24 . C25 . 113.4(3) yes C23 . C24 . C29 . 117.8(3) yes C25 . C24 . C29 . 100.1(3) yes C23 . C24 . C33 . 118.7(3) yes C25 . C24 . C33 . 103.9(3) yes C29 . C24 . C33 . 100.3(3) yes C24 . C25 . O26 . 128.0(3) yes C24 . C25 . C27 . 106.0(3) yes O26 . C25 . C27 . 126.0(3) yes C25 . C27 . C28 . 102.9(3) yes C25 . C27 . H271 . 110.7 no C28 . C27 . H271 . 111.4 no C25 . C27 . H272 . 110.2 no C28 . C27 . H272 . 112.0 no H271 . C27 . H272 . 109.6 no C27 . C28 . C29 . 102.5(3) yes C27 . C28 . C32 . 105.7(3) yes C29 . C28 . C32 . 102.0(3) yes C27 . C28 . H281 . 115.4 no C29 . C28 . H281 . 114.6 no C32 . C28 . H281 . 115.0 no C24 . C29 . C28 . 95.3(3) yes C24 . C29 . C30 . 112.9(3) yes C28 . C29 . C30 . 113.5(3) yes C24 . C29 . C31 . 112.4(3) yes C28 . C29 . C31 . 112.4(3) yes C30 . C29 . C31 . 109.8(3) yes C29 . C30 . H302 . 109.6 no C29 . C30 . H301 . 109.4 no H302 . C30 . H301 . 109.2 no C29 . C30 . H303 . 110.2 no H302 . C30 . H303 . 109.8 no H301 . C30 . H303 . 108.6 no C29 . C31 . H311 . 108.5 no C29 . C31 . H313 . 107.8 no H311 . C31 . H313 . 112.1 no C29 . C31 . H312 . 109.4 no H311 . C31 . H312 . 109.8 no H313 . C31 . H312 . 109.1 no C28 . C32 . C33 . 103.1(3) yes C28 . C32 . H322 . 111.4 no C33 . C32 . H322 . 110.8 no C28 . C32 . H321 . 111.2 no C33 . C32 . H321 . 111.0 no H322 . C32 . H321 . 109.3 no C32 . C33 . C24 . 104.8(3) yes C32 . C33 . H332 . 110.9 no C24 . C33 . H332 . 112.4 no C32 . C33 . H331 . 110.0 no C24 . C33 . H331 . 110.7 no H332 . C33 . H331 . 108.1 no H341 . O34 . H342 . 119.6 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C7 . H71 . O26 . 129 0.94 2.59 3.258(5) yes C12 . H122 . O34 1_645 163 0.95 2.45 3.372(5) yes C15 . H153 . O22 . 152 0.97 2.24 3.124(5) yes C18 . H181 . O21 2_776 143 0.96 2.54 3.356(5) yes N4 . H41 . O20 1_645 177 0.86 1.97 2.827(5) yes O34 . H341 . O21 . 169 0.82 1.71 2.519(5) yes O34 . H342 . O21 2_676 174 0.82 1.94 2.764(5) yes #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 775342' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 10-04-20 _audit_creation_method CRYSTALS_ver_14.06 _oxford_structure_analysis_title 5374 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 14.8070(5) _cell_length_b 7.0603(2) _cell_length_c 16.5075(6) _cell_angle_alpha 90 _cell_angle_beta 106.0988(16) _cell_angle_gamma 90 _cell_volume 1658.05(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986 5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C15 H15 N1 O4 Pd1 S1 # Dc = 1.65 Fooo = 896.00 Mu = 12.60 M = 411.75 # Found Formula = C16 H19 N1 O5 Pd1 S1 # Dc = 1.78 FOOO = 896.00 Mu = 12.71 M = 443.80 _chemical_formula_sum 'C16 H19 N1 O5 Pd1 S1' _chemical_formula_moiety 'C16 H19 N1 O5 Pd1 S1' _chemical_compound_source . _chemical_formula_weight 443.80 _cell_measurement_reflns_used 3895 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description lath _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.271 # Sheldrick geometric approximatio 0.93 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.95 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 16949 _reflns_number_total 3906 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections without Friedels Law is 6965 # Number of reflections with Friedels Law is 3906 # Theoretical number of reflections is about 3329 _diffrn_reflns_theta_min 5.142 _diffrn_reflns_theta_max 27.852 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.902 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -19 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 1.32 _oxford_diffrn_Wilson_scale 40.50 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.96 _refine_diff_density_max 1.04 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 3306 _refine_ls_number_restraints 0 _refine_ls_number_parameters 217 _oxford_refine_ls_R_factor_ref 0.0479 _refine_ls_wR_factor_ref 0.0832 _refine_ls_goodness_of_fit_ref 0.9252 _refine_ls_shift/su_max 0.0011707 _refine_ls_shift/su_mean 0.0000280 # The values computed from all data _oxford_reflns_number_all 3306 _refine_ls_R_factor_all 0.0479 _refine_ls_wR_factor_all 0.0832 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2525 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_gt 0.0658 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 7.97 11.0 5.39 1.56 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Pd1 Pd 0.91576(2) 0.67972(4) 0.400939(18) 0.0157 1.0000 Uani . . . . . . . C2 C 1.0456(3) 0.7697(6) 0.4403(3) 0.0196 1.0000 Uani . . . . . . . C3 C 1.0897(3) 0.8112(6) 0.5252(2) 0.0197 1.0000 Uani . . . . . . . N4 N 1.0449(2) 0.7908(5) 0.5901(2) 0.0218 1.0000 Uani . . . . . . . C5 C 0.9589(3) 0.7290(6) 0.5843(3) 0.0214 1.0000 Uani . . . . . . . O6 O 0.90149(19) 0.6800(5) 0.51635(17) 0.0218 1.0000 Uani . . . . . . . C7 C 0.9285(3) 0.7139(6) 0.6633(3) 0.0237 1.0000 Uani . . . . . . . C8 C 1.1817(3) 0.8778(6) 0.5504(3) 0.0251 1.0000 Uani . . . . . . . C9 C 1.2319(3) 0.9028(6) 0.4918(3) 0.0265 1.0000 Uani . . . . . . . C10 C 1.1919(3) 0.8608(6) 0.4075(3) 0.0235 1.0000 Uani . . . . . . . C11 C 1.0994(3) 0.7959(6) 0.3836(3) 0.0216 1.0000 Uani . . . . . . . C12 C 1.2458(3) 0.8877(8) 0.3427(3) 0.0324 1.0000 Uani . . . . . . . O13 O 0.77399(19) 0.5636(4) 0.35675(16) 0.0193 1.0000 Uani . . . . . . . S14 S 0.68179(6) 0.65362(14) 0.32713(6) 0.0162 1.0000 Uani . . . . . . . C15 C 0.6368(3) 0.6668(6) 0.4157(2) 0.0173 1.0000 Uani . . . . . . . C16 C 0.6861(3) 0.5901(6) 0.4927(3) 0.0220 1.0000 Uani . . . . . . . C17 C 0.6499(3) 0.6101(7) 0.5615(3) 0.0254 1.0000 Uani . . . . . . . C18 C 0.5651(3) 0.7020(7) 0.5548(3) 0.0267 1.0000 Uani . . . . . . . C19 C 0.5158(3) 0.7735(7) 0.4760(3) 0.0293 1.0000 Uani . . . . . . . C20 C 0.5518(3) 0.7569(7) 0.4074(3) 0.0249 1.0000 Uani . . . . . . . C21 C 0.5269(4) 0.7269(8) 0.6298(3) 0.0333 1.0000 Uani . . . . . . . O22 O 0.6847(2) 0.8449(4) 0.29686(19) 0.0258 1.0000 Uani . . . . . . . O23 O 0.61644(19) 0.5358(4) 0.26477(17) 0.0214 1.0000 Uani . . . . . . . O24 O 0.91484(18) 0.6667(4) 0.27484(16) 0.0195 1.0000 Uani . . . . . . . H71 H 0.8619 0.7332 0.6502 0.0354 1.0000 Uiso R . . . . . . H72 H 0.9587 0.8075 0.7036 0.0351 1.0000 Uiso R . . . . . . H73 H 0.9428 0.5889 0.6874 0.0355 1.0000 Uiso R . . . . . . H81 H 1.2088 0.9018 0.6078 0.0299 1.0000 Uiso R . . . . . . H91 H 1.2920 0.9477 0.5085 0.0304 1.0000 Uiso R . . . . . . H111 H 1.0733 0.7703 0.3275 0.0264 1.0000 Uiso R . . . . . . H121 H 1.2054 0.8866 0.2875 0.0524 1.0000 Uiso R . . . . . . H122 H 1.2903 0.7899 0.3471 0.0529 1.0000 Uiso R . . . . . . H123 H 1.2790 1.0030 0.3506 0.0530 1.0000 Uiso R . . . . . . H161 H 0.7427 0.5277 0.4988 0.0271 1.0000 Uiso R . . . . . . H171 H 0.6827 0.5609 0.6131 0.0322 1.0000 Uiso R . . . . . . H191 H 0.4582 0.8311 0.4719 0.0346 1.0000 Uiso R . . . . . . H201 H 0.5203 0.8068 0.3559 0.0311 1.0000 Uiso R . . . . . . H211 H 0.4612 0.7537 0.6128 0.0521 1.0000 Uiso R . . . . . . H212 H 0.5589 0.8315 0.6642 0.0521 1.0000 Uiso R . . . . . . H213 H 0.5369 0.6124 0.6639 0.0527 1.0000 Uiso R . . . . . . H4 H 1.0756 0.8257 0.6385 0.0276 1.0000 Uiso R . . . . . . H241 H 0.8975 0.7739 0.2588 0.0279 1.0000 Uiso R . . . . . . H242 H 0.8769 0.5863 0.2518 0.0279 1.0000 Uiso 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 0.01570(15) 0.01694(15) 0.01275(14) 0.00016(12) 0.00107(10) 0.00091(13) C2 0.0208(19) 0.0135(19) 0.022(2) 0.0017(15) 0.0022(16) 0.0004(15) C3 0.0207(19) 0.0154(18) 0.0199(19) 0.0027(16) 0.0007(15) 0.0045(16) N4 0.0247(17) 0.0207(19) 0.0155(16) -0.0027(14) -0.0022(13) 0.0006(15) C5 0.024(2) 0.019(2) 0.0174(19) -0.0003(16) 0.0007(16) 0.0045(16) O6 0.0219(14) 0.0268(15) 0.0150(13) -0.0015(12) 0.0021(11) -0.0005(13) C7 0.028(2) 0.025(2) 0.0157(19) 0.0028(17) 0.0028(16) 0.0043(18) C8 0.023(2) 0.025(2) 0.023(2) -0.0018(17) -0.0021(17) -0.0002(17) C9 0.0160(19) 0.023(2) 0.036(2) 0.0017(19) -0.0012(17) -0.0030(17) C10 0.021(2) 0.020(2) 0.028(2) 0.0055(17) 0.0046(17) 0.0005(16) C11 0.0207(19) 0.022(2) 0.0214(19) 0.0007(17) 0.0040(16) 0.0005(17) C12 0.023(2) 0.037(3) 0.038(3) 0.000(2) 0.009(2) -0.005(2) O13 0.0172(13) 0.0255(16) 0.0146(13) 0.0013(11) 0.0032(11) 0.0008(12) S14 0.0171(4) 0.0188(5) 0.0114(4) 0.0003(4) 0.0018(3) -0.0008(4) C15 0.0208(18) 0.0178(19) 0.0143(17) -0.0049(16) 0.0064(14) -0.0040(16) C16 0.022(2) 0.021(2) 0.021(2) 0.0026(17) 0.0034(16) -0.0001(17) C17 0.029(2) 0.032(2) 0.0150(19) 0.0025(17) 0.0060(17) -0.0035(19) C18 0.029(2) 0.029(2) 0.025(2) -0.0073(19) 0.0117(18) -0.0098(19) C19 0.022(2) 0.039(3) 0.028(2) -0.009(2) 0.0087(17) 0.0004(19) C20 0.023(2) 0.032(2) 0.0167(19) -0.0007(17) -0.0001(16) 0.0034(18) C21 0.036(3) 0.043(3) 0.027(2) -0.007(2) 0.018(2) -0.006(2) O22 0.0317(16) 0.0210(16) 0.0244(15) 0.0065(13) 0.0075(12) 0.0004(13) O23 0.0187(14) 0.0259(15) 0.0162(13) -0.0046(12) -0.0009(11) -0.0015(12) O24 0.0184(13) 0.0220(14) 0.0164(13) -0.0017(12) 0.0021(10) -0.0017(12) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.15967(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Pd1 . C2 . 1.957(4) yes Pd1 . O6 . 1.974(3) yes Pd1 . O13 . 2.182(3) yes Pd1 . O24 . 2.080(3) yes C2 . C3 . 1.404(6) yes C2 . C11 . 1.400(6) yes C3 . N4 . 1.414(5) yes C3 . C8 . 1.391(6) yes N4 . C5 . 1.325(6) yes N4 . H4 . 0.839 no C5 . O6 . 1.253(5) yes C5 . C7 . 1.497(6) yes C7 . H71 . 0.959 no C7 . H72 . 0.956 no C7 . H73 . 0.967 no C8 . C9 . 1.386(7) yes C8 . H81 . 0.936 no C9 . C10 . 1.384(6) yes C9 . H91 . 0.912 no C10 . C11 . 1.394(6) yes C10 . C12 . 1.514(6) yes C11 . H111 . 0.916 no C12 . H121 . 0.941 no C12 . H122 . 0.943 no C12 . H123 . 0.942 no O13 . S14 . 1.462(3) yes S14 . C15 . 1.769(4) yes S14 . O22 . 1.445(3) yes S14 . O23 . 1.462(3) yes C15 . C16 . 1.389(6) yes C15 . C20 . 1.383(6) yes C16 . C17 . 1.390(6) yes C16 . H161 . 0.927 no C17 . C18 . 1.390(6) yes C17 . H171 . 0.924 no C18 . C19 . 1.396(7) yes C18 . C21 . 1.509(6) yes C19 . C20 . 1.385(6) yes C19 . H191 . 0.931 no C20 . H201 . 0.918 no C21 . H211 . 0.954 no C21 . H212 . 0.971 no C21 . H213 . 0.972 no O24 . H241 . 0.820 no O24 . H242 . 0.815 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . Pd1 . O6 . 92.16(15) yes C2 . Pd1 . O13 . 176.83(14) yes O6 . Pd1 . O13 . 88.43(11) yes C2 . Pd1 . O24 . 94.57(14) yes O6 . Pd1 . O24 . 173.27(11) yes O13 . Pd1 . O24 . 84.84(10) yes Pd1 . C2 . C3 . 122.8(3) yes Pd1 . C2 . C11 . 120.7(3) yes C3 . C2 . C11 . 116.6(4) yes C2 . C3 . N4 . 123.3(4) yes C2 . C3 . C8 . 121.0(4) yes N4 . C3 . C8 . 115.7(4) yes C3 . N4 . C5 . 128.5(4) yes C3 . N4 . H4 . 116.6 no C5 . N4 . H4 . 114.9 no N4 . C5 . O6 . 123.7(4) yes N4 . C5 . C7 . 118.4(4) yes O6 . C5 . C7 . 117.9(4) yes C5 . O6 . Pd1 . 129.5(3) yes C5 . C7 . H71 . 109.3 no C5 . C7 . H72 . 111.2 no H71 . C7 . H72 . 108.3 no C5 . C7 . H73 . 109.8 no H71 . C7 . H73 . 108.5 no H72 . C7 . H73 . 109.7 no C3 . C8 . C9 . 120.4(4) yes C3 . C8 . H81 . 118.2 no C9 . C8 . H81 . 121.4 no C8 . C9 . C10 . 120.7(4) yes C8 . C9 . H91 . 120.0 no C10 . C9 . H91 . 119.3 no C9 . C10 . C11 . 118.0(4) yes C9 . C10 . C12 . 121.4(4) yes C11 . C10 . C12 . 120.6(4) yes C2 . C11 . C10 . 123.4(4) yes C2 . C11 . H111 . 119.3 no C10 . C11 . H111 . 117.3 no C10 . C12 . H121 . 111.5 no C10 . C12 . H122 . 110.4 no H121 . C12 . H122 . 108.1 no C10 . C12 . H123 . 111.6 no H121 . C12 . H123 . 108.0 no H122 . C12 . H123 . 107.2 no Pd1 . O13 . S14 . 132.15(18) yes O13 . S14 . C15 . 106.08(17) yes O13 . S14 . O22 . 114.04(18) yes C15 . S14 . O22 . 106.93(19) yes O13 . S14 . O23 . 111.26(17) yes C15 . S14 . O23 . 106.53(18) yes O22 . S14 . O23 . 111.48(18) yes S14 . C15 . C16 . 120.9(3) yes S14 . C15 . C20 . 118.9(3) yes C16 . C15 . C20 . 120.2(4) yes C15 . C16 . C17 . 119.0(4) yes C15 . C16 . H161 . 120.9 no C17 . C16 . H161 . 120.1 no C16 . C17 . C18 . 121.8(4) yes C16 . C17 . H171 . 119.5 no C18 . C17 . H171 . 118.8 no C17 . C18 . C19 . 118.1(4) yes C17 . C18 . C21 . 121.7(4) yes C19 . C18 . C21 . 120.3(4) yes C18 . C19 . C20 . 120.7(4) yes C18 . C19 . H191 . 117.3 no C20 . C19 . H191 . 122.0 no C19 . C20 . C15 . 120.3(4) yes C19 . C20 . H201 . 120.9 no C15 . C20 . H201 . 118.9 no C18 . C21 . H211 . 111.4 no C18 . C21 . H212 . 109.6 no H211 . C21 . H212 . 108.3 no C18 . C21 . H213 . 110.3 no H211 . C21 . H213 . 108.3 no H212 . C21 . H213 . 108.8 no Pd1 . O24 . H241 . 101.3 no Pd1 . O24 . H242 . 108.1 no H241 . O24 . H242 . 112.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C7 . H72 . O23 4_565 142 0.96 2.53 3.329(6) yes C11 . H111 . O24 . 122 0.92 2.38 2.967(6) yes C16 . H161 . O6 . 126 0.93 2.53 3.168(6) yes N4 . H4 . O23 4_565 163 0.84 2.23 3.040(6) yes O24 . H241 . O23 3_655 168 0.82 1.89 2.695(6) yes O24 . H242 . O22 3_645 164 0.81 1.99 2.787(6) yes