# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'J. Brown' 'Waqar Rauf' 'Amber L. Thompson' _publ_contact_author_name 'J. Brown' _publ_contact_author_email JOHN.BROWN@CHEM.OX.AC.UK _publ_section_title ; Comparative Catalytic C-H vs. C-Si Activation of Arenes with Pd Complexes Directed by Urea or Amide Groups ; # Attachment 'CrystallographicData.cif' #============================================================================== data_5 _database_code_depnum_ccdc_archive 'CCDC 724788' #============================================================================== _audit_creation_date 08-06-13 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 5877 _chemical_name_systematic ? _chemical_melting_point 'not measured' _cell_length_a 7.2492(2) _cell_length_b 8.7969(3) _cell_length_c 16.6174(6) _cell_angle_alpha 90.7614(17) _cell_angle_beta 101.0913(17) _cell_angle_gamma 100.9648(19) _cell_volume 1019.55(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 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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 2 # Given Formula = C17 H16 F2 N2 O4 Pd1 S1 # Dc = 1.59 Fooo = 532.00 Mu = 10.53 M = 488.79 # Found Formula = C19 H19 F2 N3 O4 Pd1 S1 # Dc = 1.73 FOOO = 532.00 Mu = 10.62 M = 529.84 _chemical_formula_sum 'C19 H19 F2 N3 O4 Pd1 S1' _chemical_formula_moiety 'C12 H12 F2 N3 O Pd, C7 H7 O3 S' _chemical_compound_source . _chemical_formula_weight 529.84 _cell_measurement_reflns_used 4141 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 1.062 # Sheldrick geometric approximatio 0.94 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.97 # 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 '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 14648 _reflns_number_total 4643 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections with Friedels Law is 4643 # Number of reflections without Friedels Law is 7830 # Theoretical number of reflections is about 4704 _diffrn_reflns_theta_min 5.118 _diffrn_reflns_theta_max 27.542 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.614 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 2.18 _oxford_diffrn_Wilson_scale 4.77 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.10 _refine_diff_density_max 0.88 # 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 4643 _refine_ls_number_restraints 0 _refine_ls_number_parameters 272 _oxford_refine_ls_R_factor_ref 0.0439 _refine_ls_wR_factor_ref 0.0862 _refine_ls_goodness_of_fit_ref 1.0018 _refine_ls_shift/su_max 0.000343 # The values computed from all data _oxford_reflns_number_all 4643 _refine_ls_R_factor_all 0.0439 _refine_ls_wR_factor_all 0.0862 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4061 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_gt 0.0815 # 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^) + ( 0.03P)^2^ + 1.39P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 (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. 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 0.29871(3) 0.03499(3) -0.066304(13) 0.0259 1.0000 Uani . . . . . . . O2 O 0.3721(3) 0.2433(2) -0.00695(12) 0.0304 1.0000 Uani . . . . . . . C3 C 0.3576(4) 0.2795(3) 0.06463(17) 0.0268 1.0000 Uani . . . . . . . N4 N 0.2902(3) 0.1799(3) 0.11582(14) 0.0257 1.0000 Uani . . . . . . . C5 C 0.2193(4) 0.0182(3) 0.10230(17) 0.0239 1.0000 Uani . . . . . . . C6 C 0.2104(4) -0.0658(3) 0.02911(17) 0.0249 1.0000 Uani . . . . . . . C7 C 0.1288(4) -0.2248(3) 0.02561(18) 0.0290 1.0000 Uani . . . . . . . C8 C 0.0634(4) -0.2927(3) 0.09127(19) 0.0306 1.0000 Uani . . . . . . . F9 F -0.0173(3) -0.4461(2) 0.08693(12) 0.0439 1.0000 Uani . . . . . . . C10 C 0.0787(4) -0.2071(4) 0.16329(18) 0.0292 1.0000 Uani . . . . . . . C11 C 0.1555(4) -0.0523(4) 0.16972(18) 0.0287 1.0000 Uani . . . . . . . F12 F 0.0153(3) -0.2774(2) 0.22792(11) 0.0407 1.0000 Uani . . . . . . . C13 C 0.4191(5) 0.4465(4) 0.0938(2) 0.0348 1.0000 Uani . . . . . . . N14 N 0.2296(4) -0.1608(3) -0.13820(15) 0.0304 1.0000 Uani . . . . . . . C15 C 0.2001(4) -0.2550(4) -0.18923(18) 0.0294 1.0000 Uani . . . . . . . C16 C 0.1633(5) -0.3769(4) -0.2533(2) 0.0349 1.0000 Uani . . . . . . . N17 N 0.3850(4) 0.1471(3) -0.16969(16) 0.0317 1.0000 Uani . . . . . . . C18 C 0.4253(4) 0.1925(4) -0.22903(19) 0.0313 1.0000 Uani . . . . . . . C19 C 0.4793(6) 0.2505(5) -0.3049(2) 0.0487 1.0000 Uani . . . . . . . S20 S 0.37636(10) 0.27230(9) 0.34179(4) 0.0288 1.0000 Uani . . . . . . . O21 O 0.5338(3) 0.3941(3) 0.38059(14) 0.0392 1.0000 Uani . . . . . . . O22 O 0.4274(3) 0.1221(3) 0.33193(14) 0.0366 1.0000 Uani . . . . . . . O23 O 0.2726(3) 0.3186(3) 0.26323(12) 0.0346 1.0000 Uani . . . . . . . C24 C 0.2044(4) 0.2490(4) 0.40590(17) 0.0273 1.0000 Uani . . . . . . . C25 C 0.0389(5) 0.1338(4) 0.3854(2) 0.0360 1.0000 Uani . . . . . . . C26 C -0.1018(5) 0.1225(4) 0.4318(2) 0.0398 1.0000 Uani . . . . . . . C27 C -0.0809(5) 0.2222(4) 0.4999(2) 0.0348 1.0000 Uani . . . . . . . C28 C 0.0859(5) 0.3333(4) 0.5204(2) 0.0371 1.0000 Uani . . . . . . . C29 C 0.2280(4) 0.3476(4) 0.47416(19) 0.0330 1.0000 Uani . . . . . . . C30 C -0.2364(5) 0.2108(5) 0.5488(2) 0.0474 1.0000 Uani . . . . . . . H71 H 0.1177 -0.2893 -0.0220 0.0350 1.0000 Uiso R . . . . . . H111 H 0.1664 0.0069 0.2194 0.0343 1.0000 Uiso R . . . . . . H131 H 0.4001 0.4602 0.1490 0.0542 1.0000 Uiso R . . . . . . H132 H 0.5523 0.4836 0.0929 0.0541 1.0000 Uiso R . . . . . . H133 H 0.3412 0.5051 0.0583 0.0538 1.0000 Uiso R . . . . . . H163 H 0.2207 -0.3405 -0.2983 0.0545 1.0000 Uiso R . . . . . . H162 H 0.2136 -0.4629 -0.2313 0.0542 1.0000 Uiso R . . . . . . H161 H 0.0296 -0.4067 -0.2718 0.0545 1.0000 Uiso R . . . . . . H191 H 0.3665 0.2581 -0.3438 0.0784 1.0000 Uiso R . . . . . . H192 H 0.5457 0.1792 -0.3259 0.0784 1.0000 Uiso R . . . . . . H193 H 0.5617 0.3499 -0.2949 0.0783 1.0000 Uiso R . . . . . . H251 H 0.0216 0.0652 0.3401 0.0429 1.0000 Uiso R . . . . . . H261 H -0.2142 0.0461 0.4172 0.0480 1.0000 Uiso R . . . . . . H281 H 0.1033 0.4001 0.5669 0.0461 1.0000 Uiso R . . . . . . H291 H 0.3397 0.4241 0.4888 0.0399 1.0000 Uiso R . . . . . . H301 H -0.1927 0.2764 0.5979 0.0765 1.0000 Uiso R . . . . . . H302 H -0.2741 0.1068 0.5649 0.0762 1.0000 Uiso R . . . . . . H303 H -0.3472 0.2402 0.5173 0.0764 1.0000 Uiso R . . . . . . H41 H 0.2868 0.2171 0.1632 0.0321 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 0.02714(14) 0.02868(15) 0.02380(13) 0.00205(8) 0.00901(9) 0.00634(9) O2 0.0379(11) 0.0282(11) 0.0273(10) 0.0031(8) 0.0129(9) 0.0056(9) C3 0.0289(14) 0.0278(15) 0.0253(14) 0.0029(11) 0.0071(11) 0.0080(11) N4 0.0294(12) 0.0262(13) 0.0227(11) 0.0017(9) 0.0090(9) 0.0045(10) C5 0.0198(12) 0.0252(14) 0.0278(14) 0.0037(11) 0.0054(11) 0.0064(10) C6 0.0224(13) 0.0274(15) 0.0260(14) 0.0015(11) 0.0062(11) 0.0062(11) C7 0.0335(15) 0.0270(15) 0.0283(14) 0.0006(12) 0.0099(12) 0.0070(12) C8 0.0318(15) 0.0241(15) 0.0346(16) 0.0029(12) 0.0077(13) 0.0011(12) F9 0.0629(13) 0.0259(10) 0.0410(11) 0.0005(8) 0.0204(10) -0.0058(9) C10 0.0320(15) 0.0314(16) 0.0264(14) 0.0084(12) 0.0121(12) 0.0048(12) C11 0.0288(14) 0.0315(16) 0.0260(14) 0.0002(12) 0.0066(12) 0.0053(12) F12 0.0544(12) 0.0358(11) 0.0319(10) 0.0074(8) 0.0179(9) -0.0011(9) C13 0.0476(18) 0.0256(16) 0.0324(16) 0.0018(12) 0.0147(14) 0.0031(13) N14 0.0301(13) 0.0355(15) 0.0272(13) 0.0017(11) 0.0095(10) 0.0062(11) C15 0.0279(14) 0.0328(17) 0.0299(15) 0.0060(13) 0.0108(12) 0.0067(12) C16 0.0380(17) 0.0363(18) 0.0313(16) -0.0044(13) 0.0114(13) 0.0052(13) N17 0.0334(13) 0.0339(14) 0.0306(13) 0.0018(11) 0.0107(11) 0.0090(11) C18 0.0333(16) 0.0351(17) 0.0283(15) 0.0039(13) 0.0096(12) 0.0097(13) C19 0.062(2) 0.057(2) 0.0336(18) 0.0150(16) 0.0222(17) 0.0147(19) S20 0.0279(4) 0.0337(4) 0.0247(3) -0.0009(3) 0.0086(3) 0.0027(3) O21 0.0340(12) 0.0436(14) 0.0359(12) -0.0082(10) 0.0123(10) -0.0072(10) O22 0.0358(12) 0.0401(13) 0.0370(12) -0.0010(10) 0.0088(10) 0.0134(10) O23 0.0401(12) 0.0434(13) 0.0237(10) 0.0042(9) 0.0104(9) 0.0120(10) C24 0.0280(14) 0.0321(16) 0.0225(13) 0.0030(11) 0.0058(11) 0.0070(12) C25 0.0389(17) 0.0368(18) 0.0306(16) -0.0025(13) 0.0111(13) -0.0007(14) C26 0.0331(16) 0.044(2) 0.0402(18) 0.0075(15) 0.0114(14) -0.0035(14) C27 0.0331(16) 0.0446(19) 0.0320(16) 0.0112(14) 0.0135(13) 0.0132(14) C28 0.0395(17) 0.0448(19) 0.0306(16) -0.0013(14) 0.0118(14) 0.0121(15) C29 0.0307(15) 0.0385(18) 0.0292(15) -0.0026(13) 0.0075(12) 0.0037(13) C30 0.0418(19) 0.063(3) 0.044(2) 0.0118(18) 0.0212(16) 0.0138(17) _refine_ls_extinction_coef 65(8) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.4631(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 . Pd1 2_655 3.4636(4) yes Pd1 . O2 . 1.999(2) yes Pd1 . C6 . 1.980(3) yes Pd1 . N14 . 2.008(3) yes Pd1 . N17 . 2.130(3) yes O2 . C3 . 1.256(3) yes C3 . N4 . 1.322(4) yes C3 . C13 . 1.496(4) yes N4 . C5 . 1.417(4) yes N4 . H41 . 0.855 no C5 . C6 . 1.399(4) yes C5 . C11 . 1.401(4) yes C6 . C7 . 1.407(4) yes C7 . C8 . 1.371(4) yes C7 . H71 . 0.949 no C8 . F9 . 1.360(3) yes C8 . C10 . 1.380(4) yes C10 . C11 . 1.365(4) yes C10 . F12 . 1.359(3) yes C11 . H111 . 0.952 no C13 . H131 . 0.962 no C13 . H132 . 0.962 no C13 . H133 . 0.961 no N14 . C15 . 1.138(4) yes C15 . C16 . 1.452(4) yes C16 . H163 . 0.954 no C16 . H162 . 0.949 no C16 . H161 . 0.943 no N17 . C18 . 1.138(4) yes C18 . C19 . 1.460(4) yes C19 . H191 . 0.954 no C19 . H192 . 0.960 no C19 . H193 . 0.954 no S20 . O21 . 1.449(2) yes S20 . O22 . 1.454(2) yes S20 . O23 . 1.480(2) yes S20 . C24 . 1.775(3) yes C24 . C25 . 1.398(4) yes C24 . C29 . 1.382(4) yes C25 . C26 . 1.382(4) yes C25 . H251 . 0.932 no C26 . C27 . 1.390(5) yes C26 . H261 . 0.941 no C27 . C28 . 1.384(5) yes C27 . C30 . 1.502(4) yes C28 . C29 . 1.387(4) yes C28 . H281 . 0.939 no C29 . H291 . 0.939 no C30 . H301 . 0.958 no C30 . H302 . 0.960 no C30 . H303 . 0.952 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 Pd1 2_655 Pd1 . O2 . 83.21(6) yes Pd1 2_655 Pd1 . C6 . 72.97(8) yes O2 . Pd1 . C6 . 92.26(10) yes Pd1 2_655 Pd1 . N14 . 100.05(7) yes O2 . Pd1 . N14 . 173.08(9) yes C6 . Pd1 . N14 . 94.52(11) yes Pd1 2_655 Pd1 . N17 . 108.86(7) yes O2 . Pd1 . N17 . 87.12(9) yes C6 . Pd1 . N17 . 177.97(10) yes N14 . Pd1 . N17 . 86.06(10) yes Pd1 . O2 . C3 . 128.70(19) yes O2 . C3 . N4 . 124.3(3) yes O2 . C3 . C13 . 118.0(3) yes N4 . C3 . C13 . 117.7(3) yes C3 . N4 . C5 . 128.5(2) yes C3 . N4 . H41 . 116.5 no C5 . N4 . H41 . 115.0 no N4 . C5 . C6 . 124.4(3) yes N4 . C5 . C11 . 113.5(2) yes C6 . C5 . C11 . 122.1(3) yes C5 . C6 . Pd1 . 121.9(2) yes C5 . C6 . C7 . 116.5(3) yes Pd1 . C6 . C7 . 121.6(2) yes C6 . C7 . C8 . 121.1(3) yes C6 . C7 . H71 . 121.4 no C8 . C7 . H71 . 117.5 no C7 . C8 . F9 . 120.7(3) yes C7 . C8 . C10 . 120.8(3) yes F9 . C8 . C10 . 118.5(3) yes C8 . C10 . C11 . 120.4(3) yes C8 . C10 . F12 . 119.7(3) yes C11 . C10 . F12 . 119.9(3) yes C5 . C11 . C10 . 119.0(3) yes C5 . C11 . H111 . 120.4 no C10 . C11 . H111 . 120.5 no C3 . C13 . H131 . 110.5 no C3 . C13 . H132 . 111.0 no H131 . C13 . H132 . 108.6 no C3 . C13 . H133 . 108.1 no H131 . C13 . H133 . 108.6 no H132 . C13 . H133 . 110.1 no Pd1 . N14 . C15 . 167.9(2) yes N14 . C15 . C16 . 179.1(3) yes C15 . C16 . H163 . 110.4 no C15 . C16 . H162 . 109.0 no H163 . C16 . H162 . 110.2 no C15 . C16 . H161 . 108.4 no H163 . C16 . H161 . 109.1 no H162 . C16 . H161 . 109.6 no Pd1 . N17 . C18 . 173.0(3) yes N17 . C18 . C19 . 179.3(3) yes C18 . C19 . H191 . 109.3 no C18 . C19 . H192 . 108.4 no H191 . C19 . H192 . 110.0 no C18 . C19 . H193 . 110.8 no H191 . C19 . H193 . 109.3 no H192 . C19 . H193 . 108.9 no O21 . S20 . O22 . 114.80(14) yes O21 . S20 . O23 . 112.02(14) yes O22 . S20 . O23 . 111.09(13) yes O21 . S20 . C24 . 106.94(13) yes O22 . S20 . C24 . 107.15(14) yes O23 . S20 . C24 . 104.05(13) yes S20 . C24 . C25 . 119.7(2) yes S20 . C24 . C29 . 120.9(2) yes C25 . C24 . C29 . 119.4(3) yes C24 . C25 . C26 . 119.9(3) yes C24 . C25 . H251 . 120.5 no C26 . C25 . H251 . 119.6 no C25 . C26 . C27 . 121.2(3) yes C25 . C26 . H261 . 119.7 no C27 . C26 . H261 . 119.0 no C26 . C27 . C28 . 118.1(3) yes C26 . C27 . C30 . 120.7(3) yes C28 . C27 . C30 . 121.2(3) yes C27 . C28 . C29 . 121.6(3) yes C27 . C28 . H281 . 119.0 no C29 . C28 . H281 . 119.3 no C28 . C29 . C24 . 119.8(3) yes C28 . C29 . H291 . 120.4 no C24 . C29 . H291 . 119.8 no C27 . C30 . H301 . 110.3 no C27 . C30 . H302 . 111.5 no H301 . C30 . H302 . 107.6 no C27 . C30 . H303 . 110.5 no H301 . C30 . H303 . 109.2 no H302 . C30 . H303 . 107.6 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 C11 . H111 . O22 . 136 0.95 2.44 3.194(5) yes C13 . H131 . O23 . 143 0.96 2.51 3.332(5) yes C16 . H163 . O21 2_655 142 0.95 2.55 3.349(5) yes C16 . H161 . O23 2_555 141 0.94 2.49 3.270(5) yes C29 . H291 . O21 2_666 131 0.94 2.59 3.275(5) yes N4 . H41 . O23 . 174 0.85 1.91 2.758(5) yes #============================================================================== data_8 _database_code_depnum_ccdc_archive 'CCDC 724789' #============================================================================== _audit_creation_date 08-06-13 _audit_creation_method CRYSTALS_ver_12.86 _refine_special_details ; This structure was found to be twinned using DIRAX: Rotation Angle: -1.911 Laboratory Vector: -0.6274 0.4441 0.6397 Reciprocal Cell Vector: 0.97 -1.08 8.00 Direct Cell Vector: 3.97 -5.07 12.00 H' = +1.005*H -0.021*K +0.001*L K' = +0.052*H +0.991*K L' = +0.029*H +0.011*K +0.997*L ROTAX was used to examine the possibility of this twin and the R-indices improved with the inclusion of a twin component, the scale factor for which refined to 0.236(14). ; _oxford_structure_analysis_title 5876 _chemical_name_systematic ? _chemical_melting_point 'not measured' _cell_length_a 7.5810(2) _cell_length_b 12.6494(3) _cell_length_c 13.2132(4) _cell_angle_alpha 77.4887(11) _cell_angle_beta 82.2803(12) _cell_angle_gamma 73.9961(12) _cell_volume 1185.29(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 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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 2 # Given Formula = C17 H16 F2 N2 O4 Pd1 S1 # Dc = 1.37 Fooo = 576.00 Mu = 9.06 M = 488.79 # Found Formula = C21 H22 F2 N4 O4 Pd1 S1 # Dc = 1.60 FOOO = 576.00 Mu = 9.21 M = 570.89 _chemical_formula_sum 'C21 H22 F2 N4 O4 Pd1 S1' _chemical_formula_moiety 'C12 H12 F2 N3 O Pd, C7 H7 O3 S, C2 H3 N' _chemical_compound_source . _chemical_formula_weight 570.89 _cell_measurement_reflns_used 4555 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.921 # Sheldrick geometric approximatio 0.92 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.73 _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 '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 16083 _reflns_number_total 5124 _diffrn_reflns_av_R_equivalents 0.127 # Number of reflections with Friedels Law is 5124 # Number of reflections without Friedels Law is 8464 # Theoretical number of reflections is about 5379 _diffrn_reflns_theta_min 5.122 _diffrn_reflns_theta_max 27.417 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.224 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -15 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 3.10 _oxford_diffrn_Wilson_scale 4.26 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.48 _refine_diff_density_max 1.92 # 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>2.0\s(I) _refine_ls_number_reflns 4225 _refine_ls_number_restraints 0 _refine_ls_number_parameters 299 _oxford_refine_ls_R_factor_ref 0.0679 _refine_ls_wR_factor_ref 0.0794 _refine_ls_goodness_of_fit_ref 0.9889 _refine_ls_shift/su_max 0.000313 # The values computed from all data _oxford_reflns_number_all 5123 _refine_ls_R_factor_all 0.0815 _refine_ls_wR_factor_all 0.1026 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4225 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_gt 0.0794 # 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 F _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, 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: 1.41 1.14 0.768 ; # 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. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. 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 0.20747(5) 0.10306(3) 0.00009(3) 0.0384 1.0000 Uani . . . . . . . O2 O 0.3462(6) 0.0880(3) -0.1360(3) 0.0482 1.0000 Uani . . . . . . . C3 C 0.4290(7) 0.0005(4) -0.1703(4) 0.0401 1.0000 Uani . . . . . . . N4 N 0.4269(6) -0.1019(3) -0.1217(3) 0.0377 1.0000 Uani . . . . . . . C5 C 0.3288(6) -0.1353(4) -0.0230(4) 0.0362 1.0000 Uani . . . . . . . C6 C 0.2296(7) -0.0607(4) 0.0368(4) 0.0367 1.0000 Uani . . . . . . . C7 C 0.1434(7) -0.1125(4) 0.1285(4) 0.0407 1.0000 Uani . . . . . . . F8 F 0.0380(6) -0.0533(3) 0.1991(3) 0.0604 1.0000 Uani . . . . . . . C9 C 0.1606(8) -0.2253(4) 0.1546(4) 0.0453 1.0000 Uani . . . . . . . F10 F 0.0725(6) -0.2669(3) 0.2447(3) 0.0628 1.0000 Uani . . . . . . . C11 C 0.2641(8) -0.2984(4) 0.0924(4) 0.0434 1.0000 Uani . . . . . . . C12 C 0.3486(7) -0.2515(4) 0.0005(4) 0.0415 1.0000 Uani . . . . . . . C13 C 0.5401(9) 0.0126(5) -0.2739(4) 0.0486 1.0000 Uani . . . . . . . N14 N 0.2025(6) 0.2739(4) -0.0421(4) 0.0441 1.0000 Uani . . . . . . . C15 C 0.2109(6) 0.3648(4) -0.0530(3) 0.0361 1.0000 Uani . . . . . . . C16 C 0.2240(7) 0.4788(4) -0.0642(4) 0.0408 1.0000 Uani . . . . . . . N17 N 0.0607(6) 0.1458(4) 0.1275(4) 0.0431 1.0000 Uani . . . . . . . C18 C -0.0287(7) 0.1929(4) 0.1890(4) 0.0422 1.0000 Uani . . . . . . . C19 C -0.1425(9) 0.2502(5) 0.2674(5) 0.0547 1.0000 Uani . . . . . . . S20 S 0.70275(17) 0.62763(10) 0.76233(8) 0.0364 1.0000 Uani . . . . . . . O21 O 0.5611(6) 0.5803(3) 0.8263(3) 0.0460 1.0000 Uani . . . . . . . O22 O 0.6702(6) 0.7462(3) 0.7631(3) 0.0498 1.0000 Uani . . . . . . . O23 O 0.8866(6) 0.5631(4) 0.7866(3) 0.0532 1.0000 Uani . . . . . . . C24 C 0.6809(6) 0.6193(4) 0.6321(3) 0.0363 1.0000 Uani . . . . . . . C25 C 0.5659(8) 0.7067(5) 0.5700(4) 0.0457 1.0000 Uani . . . . . . . C26 C 0.5484(9) 0.6973(6) 0.4687(4) 0.0550 1.0000 Uani . . . . . . . C27 C 0.6447(9) 0.6040(6) 0.4290(4) 0.0561 1.0000 Uani . . . . . . . C28 C 0.7566(9) 0.5169(6) 0.4927(5) 0.0578 1.0000 Uani . . . . . . . C29 C 0.7752(9) 0.5245(5) 0.5945(4) 0.0511 1.0000 Uani . . . . . . . C30 C 0.6295(12) 0.5948(9) 0.3168(5) 0.0820 1.0000 Uani . . . . . . . N31 N 0.2406(10) -0.0302(6) 0.5333(6) 0.0845 1.0000 Uani . . . . . . . C32 C 0.1591(10) 0.0599(6) 0.5363(5) 0.0601 1.0000 Uani . . . . . . . C33 C 0.0526(12) 0.1737(6) 0.5367(6) 0.0728 1.0000 Uani . . . . . . . H41 H 0.4942 -0.1591 -0.1545 0.0456 1.0000 Uiso R . . . . . . H111 H 0.2752 -0.3763 0.1115 0.0500 1.0000 Uiso R . . . . . . H121 H 0.4190 -0.2958 -0.0454 0.0522 1.0000 Uiso R . . . . . . H132 H 0.5824 -0.0598 -0.2946 0.0730 1.0000 Uiso R . . . . . . H131 H 0.6441 0.0401 -0.2649 0.0730 1.0000 Uiso R . . . . . . H133 H 0.4674 0.0670 -0.3246 0.0732 1.0000 Uiso R . . . . . . H163 H 0.1385 0.5312 -0.1101 0.0600 1.0000 Uiso R . . . . . . H161 H 0.2026 0.5033 0.0016 0.0600 1.0000 Uiso R . . . . . . H162 H 0.3468 0.4848 -0.0924 0.0599 1.0000 Uiso R . . . . . . H191 H -0.0767 0.2973 0.2884 0.0748 1.0000 Uiso R . . . . . . H192 H -0.1731 0.1966 0.3256 0.0752 1.0000 Uiso R . . . . . . H193 H -0.2518 0.2978 0.2376 0.0751 1.0000 Uiso R . . . . . . H251 H 0.5006 0.7722 0.5951 0.0509 1.0000 Uiso R . . . . . . H261 H 0.4750 0.7584 0.4258 0.0632 1.0000 Uiso R . . . . . . H281 H 0.8198 0.4506 0.4680 0.0710 1.0000 Uiso R . . . . . . H291 H 0.8462 0.4638 0.6384 0.0581 1.0000 Uiso R . . . . . . H301 H 0.7245 0.5319 0.2988 0.1440 1.0000 Uiso R . . . . . . H303 H 0.6395 0.6633 0.2701 0.1441 1.0000 Uiso R . . . . . . H302 H 0.5112 0.5807 0.3143 0.1440 1.0000 Uiso R . . . . . . H332 H 0.0734 0.1969 0.5979 0.1071 1.0000 Uiso R . . . . . . H331 H -0.0770 0.1805 0.5366 0.1071 1.0000 Uiso R . . . . . . H333 H 0.0913 0.2239 0.4767 0.1071 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 0.0466(2) 0.0329(2) 0.0352(2) -0.00451(14) -0.00538(15) -0.01002(15) O2 0.064(2) 0.0383(19) 0.0374(19) -0.0013(15) 0.0019(17) -0.0129(17) C3 0.045(2) 0.040(2) 0.034(2) -0.0033(19) -0.0091(19) -0.009(2) N4 0.045(2) 0.0366(19) 0.0297(19) -0.0021(15) -0.0023(16) -0.0103(16) C5 0.041(2) 0.035(2) 0.031(2) 0.0038(17) -0.0107(18) -0.0109(18) C6 0.044(2) 0.030(2) 0.038(2) -0.0038(18) -0.0139(19) -0.0093(18) C7 0.052(3) 0.035(2) 0.031(2) -0.0048(18) 0.004(2) -0.009(2) F8 0.093(3) 0.0424(17) 0.0435(18) -0.0096(14) 0.0144(17) -0.0210(17) C9 0.064(3) 0.040(3) 0.029(2) 0.0018(19) 0.000(2) -0.017(2) F10 0.099(3) 0.0450(18) 0.0379(17) -0.0004(13) 0.0143(17) -0.0230(18) C11 0.057(3) 0.034(2) 0.037(2) 0.0024(19) -0.012(2) -0.011(2) C12 0.046(3) 0.046(3) 0.035(2) -0.007(2) -0.005(2) -0.014(2) C13 0.065(3) 0.046(3) 0.032(2) 0.001(2) 0.003(2) -0.019(2) N14 0.048(2) 0.039(2) 0.044(2) -0.0121(18) -0.0059(19) -0.0066(18) C15 0.043(2) 0.042(3) 0.0220(19) -0.0058(17) -0.0006(17) -0.0098(19) C16 0.050(3) 0.039(2) 0.033(2) -0.0017(18) -0.0035(19) -0.013(2) N17 0.049(2) 0.039(2) 0.043(2) -0.0071(18) -0.0088(19) -0.0117(18) C18 0.049(3) 0.037(2) 0.039(3) -0.002(2) -0.007(2) -0.012(2) C19 0.065(3) 0.053(3) 0.042(3) -0.006(2) 0.009(3) -0.016(3) S20 0.0463(6) 0.0372(6) 0.0234(5) -0.0024(4) -0.0010(4) -0.0103(5) O21 0.063(2) 0.048(2) 0.0276(16) -0.0030(14) 0.0036(15) -0.0209(17) O22 0.073(3) 0.044(2) 0.0351(18) -0.0098(15) 0.0044(17) -0.0211(18) O23 0.052(2) 0.064(2) 0.0397(19) -0.0099(18) -0.0086(16) -0.0058(18) C24 0.042(2) 0.042(2) 0.0211(19) -0.0007(17) 0.0033(17) -0.0120(19) C25 0.050(3) 0.044(3) 0.034(2) 0.000(2) -0.001(2) -0.005(2) C26 0.060(3) 0.065(4) 0.030(2) 0.010(2) -0.004(2) -0.016(3) C27 0.069(4) 0.074(4) 0.030(3) -0.004(2) -0.002(2) -0.030(3) C28 0.072(4) 0.064(4) 0.039(3) -0.023(3) 0.006(3) -0.014(3) C29 0.063(3) 0.045(3) 0.041(3) -0.008(2) -0.009(2) -0.005(2) C30 0.096(6) 0.136(8) 0.027(3) -0.020(4) 0.005(3) -0.053(5) N31 0.076(4) 0.077(5) 0.094(5) 0.000(4) -0.012(4) -0.017(3) C32 0.065(4) 0.066(4) 0.049(3) 0.002(3) -0.010(3) -0.023(3) C33 0.092(5) 0.061(4) 0.063(4) -0.008(3) 0.000(4) -0.023(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.555(5) loop_ _oxford_twin_element_scale_factors 0.764(14) 0.236(14) 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 . 1.976(4) yes Pd1 . C6 . 1.988(5) yes Pd1 . N14 . 2.102(4) yes Pd1 . N17 . 1.981(5) yes O2 . C3 . 1.257(7) yes C3 . N4 . 1.319(6) yes C3 . C13 . 1.509(7) yes N4 . C5 . 1.451(6) yes N4 . H41 . 0.920 no C5 . C6 . 1.361(8) yes C5 . C12 . 1.405(7) yes C6 . C7 . 1.416(7) yes C7 . F8 . 1.357(6) yes C7 . C9 . 1.367(7) yes C9 . F10 . 1.360(6) yes C9 . C11 . 1.378(8) yes C11 . C12 . 1.387(7) yes C11 . H111 . 0.947 no C12 . H121 . 0.928 no C13 . H132 . 0.969 no C13 . H131 . 0.975 no C13 . H133 . 0.957 no N14 . C15 . 1.146(7) yes C15 . C16 . 1.447(7) yes C16 . H163 . 0.960 no C16 . H161 . 0.964 no C16 . H162 . 0.972 no N17 . C18 . 1.147(7) yes C18 . C19 . 1.443(8) yes C19 . H191 . 0.975 no C19 . H192 . 0.959 no C19 . H193 . 0.956 no S20 . O21 . 1.455(4) yes S20 . O22 . 1.453(4) yes S20 . O23 . 1.446(4) yes S20 . C24 . 1.779(5) yes C24 . C25 . 1.387(7) yes C24 . C29 . 1.373(8) yes C25 . C26 . 1.396(8) yes C25 . H251 . 0.944 no C26 . C27 . 1.375(10) yes C26 . H261 . 0.941 no C27 . C28 . 1.385(9) yes C27 . C30 . 1.534(8) yes C28 . C29 . 1.397(8) yes C28 . H281 . 0.947 no C29 . H291 . 0.938 no C30 . H301 . 0.963 no C30 . H303 . 0.964 no C30 . H302 . 0.967 no N31 . C32 . 1.143(10) yes C32 . C33 . 1.444(11) yes C33 . H332 . 0.964 no C33 . H331 . 0.963 no C33 . H333 . 0.969 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 . 91.39(18) yes O2 . Pd1 . N14 . 85.99(17) yes C6 . Pd1 . N14 . 176.24(18) yes O2 . Pd1 . N17 . 170.29(16) yes C6 . Pd1 . N17 . 98.2(2) yes N14 . Pd1 . N17 . 84.47(18) yes Pd1 . O2 . C3 . 129.1(3) yes O2 . C3 . N4 . 124.5(5) yes O2 . C3 . C13 . 118.2(5) yes N4 . C3 . C13 . 117.3(5) yes C3 . N4 . C5 . 127.8(4) yes C3 . N4 . H41 . 116.3 no C5 . N4 . H41 . 115.8 no N4 . C5 . C6 . 122.8(4) yes N4 . C5 . C12 . 111.6(4) yes C6 . C5 . C12 . 125.6(5) yes C5 . C6 . Pd1 . 123.9(4) yes C5 . C6 . C7 . 112.6(4) yes Pd1 . C6 . C7 . 123.4(4) yes C6 . C7 . F8 . 122.2(4) yes C6 . C7 . C9 . 123.5(5) yes F8 . C7 . C9 . 114.3(4) yes C7 . C9 . F10 . 118.9(5) yes C7 . C9 . C11 . 122.2(5) yes F10 . C9 . C11 . 118.9(5) yes C9 . C11 . C12 . 116.6(5) yes C9 . C11 . H111 . 121.3 no C12 . C11 . H111 . 122.1 no C5 . C12 . C11 . 119.5(5) yes C5 . C12 . H121 . 119.4 no C11 . C12 . H121 . 121.1 no C3 . C13 . H132 . 109.0 no C3 . C13 . H131 . 107.3 no H132 . C13 . H131 . 110.7 no C3 . C13 . H133 . 110.0 no H132 . C13 . H133 . 111.5 no H131 . C13 . H133 . 108.2 no Pd1 . N14 . C15 . 170.8(4) yes N14 . C15 . C16 . 178.4(5) yes C15 . C16 . H163 . 112.7 no C15 . C16 . H161 . 112.0 no H163 . C16 . H161 . 107.6 no C15 . C16 . H162 . 110.3 no H163 . C16 . H162 . 107.3 no H161 . C16 . H162 . 106.6 no Pd1 . N17 . C18 . 165.5(4) yes N17 . C18 . C19 . 178.9(6) yes C18 . C19 . H191 . 109.2 no C18 . C19 . H192 . 109.7 no H191 . C19 . H192 . 111.0 no C18 . C19 . H193 . 108.5 no H191 . C19 . H193 . 108.1 no H192 . C19 . H193 . 110.2 no O21 . S20 . O22 . 111.8(2) yes O21 . S20 . O23 . 112.5(2) yes O22 . S20 . O23 . 113.5(3) yes O21 . S20 . C24 . 106.2(2) yes O22 . S20 . C24 . 105.7(2) yes O23 . S20 . C24 . 106.5(2) yes S20 . C24 . C25 . 120.2(4) yes S20 . C24 . C29 . 119.5(4) yes C25 . C24 . C29 . 120.3(5) yes C24 . C25 . C26 . 119.2(5) yes C24 . C25 . H251 . 120.9 no C26 . C25 . H251 . 119.9 no C25 . C26 . C27 . 121.3(5) yes C25 . C26 . H261 . 118.7 no C27 . C26 . H261 . 119.8 no C26 . C27 . C28 . 118.6(5) yes C26 . C27 . C30 . 121.5(6) yes C28 . C27 . C30 . 119.9(7) yes C27 . C28 . C29 . 120.9(6) yes C27 . C28 . H281 . 120.0 no C29 . C28 . H281 . 119.1 no C28 . C29 . C24 . 119.7(5) yes C28 . C29 . H291 . 120.4 no C24 . C29 . H291 . 119.8 no C27 . C30 . H301 . 109.2 no C27 . C30 . H303 . 110.0 no H301 . C30 . H303 . 111.0 no C27 . C30 . H302 . 107.4 no H301 . C30 . H302 . 108.5 no H303 . C30 . H302 . 110.7 no N31 . C32 . C33 . 177.7(8) yes C32 . C33 . H332 . 109.3 no C32 . C33 . H331 . 111.4 no H332 . C33 . H331 . 108.7 no C32 . C33 . H333 . 110.4 no H332 . C33 . H333 . 107.5 no H331 . C33 . H333 . 109.3 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 N4 . H41 . O22 1_544 166 0.92 1.92 2.824(8) yes C11 . H111 . O21 2_656 156 0.95 2.54 3.427(8) yes C12 . H121 . O21 1_544 171 0.93 2.49 3.415(8) yes C13 . H132 . O22 1_544 146 0.97 2.34 3.186(8) yes C16 . H163 . O23 1_454 148 0.96 2.39 3.241(8) yes C16 . H162 . O21 1_554 154 0.97 2.30 3.207(8) yes C19 . H191 . O23 2_666 142 0.98 2.54 3.357(8) yes C19 . H193 . O21 2_566 175 0.96 2.56 3.515(8) yes #============================================================================== data_16 _database_code_depnum_ccdc_archive 'CCDC 724790' #============================================================================== _audit_creation_date 09-03-02 _audit_creation_method CRYSTALS_ver_12.87 _refine_special_details ; On initial refinement, the tosylate oxygen ADPs were prolate and a small, but significant amount of residual electron density was visible between the atoms. Examination of the slant Fourier clearly showed the presence of a second orientation for the SO~3~ group, which was modelled with an occupancy of 27.4%, however restraints were required to maintain a sensible geometry and thermal parameters. ; _oxford_structure_analysis_title 6066 _chemical_name_systematic ? _chemical_melting_point 'not measured' _cell_length_a 7.4418(1) _cell_length_b 14.5003(2) _cell_length_c 20.7460(3) _cell_angle_alpha 90 _cell_angle_beta 96.2239(5) _cell_angle_gamma 90 _cell_volume 2225.47(5) _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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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 = C20 H23 F1 N4 O4 Pd1 S1 # Dc = 1.61 Fooo = 1096.00 Mu = 9.70 M = 540.89 # Found Formula = C20 H23 F1 N4 O4 Pd1 S1 # Dc = 1.61 FOOO = 1096.00 Mu = 9.70 M = 540.89 _chemical_formula_sum 'C20 H23 F1 N4 O4 Pd1 S1' _chemical_formula_moiety 'C13 H16 F N4 O Pd, C7 H7 O3 S' _chemical_compound_source . _chemical_formula_weight 540.89 _cell_measurement_reflns_used 5196 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_max 0.59 _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.970 # Sheldrick geometric approximatio 0.93 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.94 # 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 '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 41900 _reflns_number_total 5061 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections with Friedels Law is 5061 # Number of reflections without Friedels Law is 9872 # Theoretical number of reflections is about 5107 _diffrn_reflns_theta_min 5.106 _diffrn_reflns_theta_max 27.490 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.940 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 2.37 _oxford_diffrn_Wilson_scale 20.45 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.69 _refine_diff_density_max 0.75 # 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 5060 _refine_ls_number_restraints 48 _refine_ls_number_parameters 308 _oxford_refine_ls_R_factor_ref 0.0506 _refine_ls_wR_factor_ref 0.0882 _refine_ls_goodness_of_fit_ref 0.9640 _refine_ls_shift/su_max 0.001100 # The values computed from all data _oxford_reflns_number_all 5060 _refine_ls_R_factor_all 0.0506 _refine_ls_wR_factor_all 0.0882 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3944 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_gt 0.0727 # 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: 9.72 13.6 6.85 2.05 ; # 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 (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. 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 0.33897(3) 0.490852(16) 0.547403(11) 0.0286 1.0000 Uani . . . . . . . O2 O 0.2008(4) 0.42493(17) 0.47448(12) 0.0394 1.0000 Uani . . . . . . . C3 C 0.1220(4) 0.4546(2) 0.42190(17) 0.0314 1.0000 Uani . . . . . . . N4 N 0.1135(4) 0.54476(19) 0.40674(13) 0.0304 1.0000 Uani . . . . . . . C5 C 0.1846(4) 0.6192(2) 0.44533(15) 0.0267 1.0000 Uani . . . . . . . C6 C 0.2865(4) 0.6114(2) 0.50569(15) 0.0276 1.0000 Uani . . . . . . . C7 C 0.3497(5) 0.6934(2) 0.53599(16) 0.0357 1.0000 Uani . . . . . . . C8 C 0.3156(5) 0.7796(2) 0.50848(18) 0.0389 1.0000 Uani . . . . . . . C9 C 0.2159(5) 0.7827(2) 0.44924(17) 0.0344 1.0000 Uani . . . . . . . C10 C 0.1478(4) 0.7063(2) 0.41701(16) 0.0310 1.0000 Uani . . . . . . . F11 F 0.1799(3) 0.86678(14) 0.41961(12) 0.0472 1.0000 Uani . . . . . . . N12 N 0.0457(4) 0.3930(2) 0.37895(15) 0.0392 1.0000 Uani . . . . . . . C13 C -0.0683(5) 0.4184(3) 0.32041(19) 0.0465 1.0000 Uani . . . . . . . C14 C 0.0714(7) 0.2943(3) 0.3924(2) 0.0581 1.0000 Uani . . . . . . . N15 N 0.3803(4) 0.3615(2) 0.59630(15) 0.0389 1.0000 Uani . . . . . . . C16 C 0.4127(5) 0.3052(2) 0.63335(18) 0.0378 1.0000 Uani . . . . . . . C17 C 0.4527(6) 0.2349(3) 0.6830(2) 0.0464 1.0000 Uani . . . . . . . N18 N 0.4744(4) 0.5430(2) 0.62775(14) 0.0344 1.0000 Uani . . . . . . . C19 C 0.5414(5) 0.5570(3) 0.67877(17) 0.0357 1.0000 Uani . . . . . . . C20 C 0.6226(6) 0.5719(3) 0.74463(19) 0.0511 1.0000 Uani . . . . . . . S21 S -0.00135(15) 0.66750(6) 0.23029(4) 0.0423 1.0000 Uani D . . . . . . C25 C -0.0862(5) 0.5889(2) 0.16892(16) 0.0337 1.0000 Uani . . . . . . . C26 C 0.0292(5) 0.5465(3) 0.13014(17) 0.0379 1.0000 Uani . . . . . . . C27 C -0.0399(5) 0.4846(3) 0.08301(17) 0.0401 1.0000 Uani . . . . . . . C28 C -0.2224(6) 0.4635(3) 0.07380(18) 0.0423 1.0000 Uani . . . . . . . C29 C -0.3359(6) 0.5078(3) 0.1130(2) 0.0480 1.0000 Uani . . . . . . . C30 C -0.2701(5) 0.5697(3) 0.16029(19) 0.0424 1.0000 Uani . . . . . . . C31 C -0.2937(7) 0.3949(3) 0.0221(2) 0.0591 1.0000 Uani . . . . . . . H71 H 0.4178 0.6907 0.5765 0.0431 1.0000 Uiso R . . . . . . H81 H 0.3575 0.8330 0.5297 0.0468 1.0000 Uiso R . . . . . . H101 H 0.0784 0.7117 0.3770 0.0369 1.0000 Uiso R . . . . . . H132 H -0.1527 0.3694 0.3100 0.0697 1.0000 Uiso R . . . . . . H131 H -0.1337 0.4746 0.3267 0.0698 1.0000 Uiso R . . . . . . H133 H 0.0037 0.4262 0.2853 0.0699 1.0000 Uiso R . . . . . . H143 H 0.0963 0.2628 0.3540 0.0874 1.0000 Uiso R . . . . . . H141 H -0.0339 0.2693 0.4075 0.0877 1.0000 Uiso R . . . . . . H142 H 0.1703 0.2852 0.4249 0.0873 1.0000 Uiso R . . . . . . H171 H 0.4733 0.1772 0.6627 0.0689 1.0000 Uiso R . . . . . . H172 H 0.5580 0.2517 0.7110 0.0691 1.0000 Uiso R . . . . . . H173 H 0.3519 0.2293 0.7075 0.0689 1.0000 Uiso R . . . . . . H203 H 0.6932 0.6271 0.7468 0.0769 1.0000 Uiso R . . . . . . H201 H 0.5305 0.5775 0.7728 0.0770 1.0000 Uiso R . . . . . . H202 H 0.6976 0.5208 0.7580 0.0770 1.0000 Uiso R . . . . . . H261 H 0.1519 0.5599 0.1358 0.0460 1.0000 Uiso R . . . . . . H271 H 0.0384 0.4564 0.0572 0.0480 1.0000 Uiso R . . . . . . H291 H -0.4585 0.4954 0.1075 0.0580 1.0000 Uiso R . . . . . . H301 H -0.3487 0.5985 0.1865 0.0509 1.0000 Uiso R . . . . . . H312 H -0.4067 0.4159 0.0004 0.0890 1.0000 Uiso R . . . . . . H311 H -0.2095 0.3868 -0.0092 0.0893 1.0000 Uiso R . . . . . . H313 H -0.3128 0.3364 0.0418 0.0891 1.0000 Uiso R . . . . . . H41 H 0.0676 0.5582 0.3690 0.0361 1.0000 Uiso R . . . . . . O220 O -0.0766(6) 0.6329(3) 0.28947(17) 0.0520 0.726(6) Uani D . P . 1 . . O230 O -0.0976(7) 0.7541(3) 0.2124(2) 0.0585 0.726(6) Uani D . P . 1 . . O240 O 0.1846(5) 0.6688(4) 0.2328(2) 0.0613 0.726(6) Uani D . P . 1 . . O221 O 0.1320(17) 0.6110(7) 0.2734(5) 0.0616 0.274(6) Uani D . P . 2 . . O231 O -0.1259(14) 0.7172(10) 0.2601(7) 0.0654 0.274(6) Uani D . P . 2 . . O241 O 0.1306(18) 0.7283(9) 0.1988(6) 0.0658 0.274(6) Uani D . P . 2 . . 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 0.03114(13) 0.03009(12) 0.02511(12) 0.00309(10) 0.00610(8) 0.00207(10) O2 0.0504(15) 0.0302(12) 0.0367(13) 0.0015(10) 0.0010(11) -0.0056(11) C3 0.0290(16) 0.0339(16) 0.0332(17) -0.0037(13) 0.0120(13) -0.0012(13) N4 0.0341(15) 0.0314(14) 0.0251(13) -0.0020(10) 0.0012(11) -0.0006(11) C5 0.0243(15) 0.0283(14) 0.0281(15) -0.0028(12) 0.0051(12) -0.0008(11) C6 0.0290(15) 0.0276(14) 0.0263(15) -0.0011(12) 0.0041(12) 0.0009(12) C7 0.0426(19) 0.0346(17) 0.0281(17) -0.0022(13) -0.0046(14) -0.0032(15) C8 0.053(2) 0.0277(16) 0.0350(18) -0.0045(13) -0.0007(16) -0.0067(15) C9 0.0397(18) 0.0254(15) 0.0378(18) 0.0046(13) 0.0031(15) 0.0014(13) C10 0.0283(16) 0.0342(16) 0.0296(16) 0.0005(13) -0.0010(13) 0.0022(13) F11 0.0548(14) 0.0290(10) 0.0554(14) 0.0096(9) -0.0046(11) 0.0000(9) N12 0.0441(17) 0.0354(15) 0.0387(16) -0.0120(13) 0.0074(13) -0.0095(13) C13 0.0358(19) 0.061(2) 0.043(2) -0.0201(18) 0.0028(16) -0.0078(17) C14 0.076(3) 0.033(2) 0.067(3) -0.0116(19) 0.012(2) -0.012(2) N15 0.0439(17) 0.0365(16) 0.0375(16) 0.0080(13) 0.0095(13) 0.0039(13) C16 0.043(2) 0.0329(17) 0.0378(19) 0.0022(14) 0.0071(16) -0.0005(14) C17 0.060(3) 0.0383(19) 0.040(2) 0.0111(16) -0.0014(18) 0.0054(17) N18 0.0319(15) 0.0404(15) 0.0310(15) 0.0054(12) 0.0038(12) 0.0061(12) C19 0.0307(17) 0.0426(19) 0.0336(18) 0.0067(14) 0.0022(14) 0.0056(14) C20 0.052(2) 0.066(3) 0.0322(19) 0.0039(18) -0.0088(17) 0.007(2) S21 0.0608(6) 0.0370(5) 0.0272(4) 0.0008(3) -0.0036(4) -0.0027(4) C25 0.046(2) 0.0278(15) 0.0255(16) 0.0049(12) -0.0029(14) 0.0024(14) C26 0.0363(18) 0.0447(19) 0.0318(17) 0.0047(14) -0.0006(14) 0.0075(15) C27 0.048(2) 0.0389(18) 0.0329(17) 0.0006(14) 0.0024(15) 0.0111(16) C28 0.054(2) 0.0375(18) 0.0351(18) -0.0039(15) 0.0047(16) -0.0027(16) C29 0.043(2) 0.055(2) 0.046(2) -0.0115(19) 0.0071(16) -0.0095(18) C30 0.041(2) 0.045(2) 0.043(2) -0.0078(16) 0.0103(16) 0.0002(16) C31 0.070(3) 0.054(3) 0.054(3) -0.020(2) 0.009(2) -0.011(2) O220 0.063(3) 0.065(3) 0.0263(18) 0.0035(17) -0.0031(17) -0.015(2) O230 0.084(3) 0.036(2) 0.051(3) -0.0045(18) -0.014(2) 0.003(2) O240 0.042(2) 0.087(4) 0.054(3) -0.022(3) -0.0050(19) -0.012(2) O221 0.097(10) 0.049(6) 0.033(6) -0.002(5) -0.020(6) 0.017(6) O231 0.055(7) 0.075(9) 0.065(9) -0.034(7) 0.002(6) 0.007(6) O241 0.095(10) 0.062(8) 0.040(6) -0.002(6) 0.008(6) -0.029(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.23036(14) 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 . Pd1 2_666 3.2719(5) yes Pd1 . O2 . 1.980(2) yes Pd1 . C6 . 1.970(3) yes Pd1 . N15 . 2.138(3) yes Pd1 . N18 . 2.000(3) yes O2 . C3 . 1.257(4) yes C3 . N4 . 1.345(4) yes C3 . N12 . 1.344(4) yes N4 . C5 . 1.412(4) yes N4 . H41 . 0.842 no C5 . C6 . 1.397(4) yes C5 . C10 . 1.406(4) yes C6 . C7 . 1.403(4) yes C7 . C8 . 1.386(5) yes C7 . H71 . 0.933 no C8 . C9 . 1.366(5) yes C8 . H81 . 0.928 no C9 . C10 . 1.363(5) yes C9 . F11 . 1.379(4) yes C10 . H101 . 0.933 no N12 . C13 . 1.451(5) yes N12 . C14 . 1.466(5) yes C13 . H132 . 0.958 no C13 . H131 . 0.966 no C13 . H133 . 0.957 no C14 . H143 . 0.954 no C14 . H141 . 0.946 no C14 . H142 . 0.952 no N15 . C16 . 1.130(5) yes C16 . C17 . 1.456(5) yes C17 . H171 . 0.956 no C17 . H172 . 0.955 no C17 . H173 . 0.955 no N18 . C19 . 1.138(5) yes C19 . C20 . 1.449(5) yes C20 . H203 . 0.955 no C20 . H201 . 0.951 no C20 . H202 . 0.950 no S21 . C25 . 1.774(3) yes S21 . O220 . 1.490(4) yes S21 . O230 . 1.474(4) yes S21 . O240 . 1.379(4) yes C25 . C26 . 1.383(5) yes C25 . C30 . 1.389(5) yes C26 . C27 . 1.385(5) yes C26 . H261 . 0.929 no C27 . C28 . 1.384(6) yes C27 . H271 . 0.929 no C28 . C29 . 1.392(6) yes C28 . C31 . 1.516(5) yes C29 . C30 . 1.379(5) yes C29 . H291 . 0.925 no C30 . H301 . 0.939 no C31 . H312 . 0.960 no C31 . H311 . 0.957 no C31 . H313 . 0.958 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 Pd1 2_666 Pd1 . O2 . 86.18(8) yes Pd1 2_666 Pd1 . C6 . 77.72(9) yes O2 . Pd1 . C6 . 91.76(12) yes Pd1 2_666 Pd1 . N15 . 106.21(8) yes O2 . Pd1 . N15 . 88.58(11) yes C6 . Pd1 . N15 . 176.06(12) yes Pd1 2_666 Pd1 . N18 . 97.74(8) yes O2 . Pd1 . N18 . 172.68(11) yes C6 . Pd1 . N18 . 95.10(13) yes N15 . Pd1 . N18 . 84.40(12) yes Pd1 . O2 . C3 . 130.7(2) yes O2 . C3 . N4 . 122.8(3) yes O2 . C3 . N12 . 118.2(3) yes N4 . C3 . N12 . 119.0(3) yes C3 . N4 . C5 . 127.3(3) yes C3 . N4 . H41 . 116.6 no C5 . N4 . H41 . 116.0 no N4 . C5 . C6 . 125.4(3) yes N4 . C5 . C10 . 113.9(3) yes C6 . C5 . C10 . 120.7(3) yes C5 . C6 . Pd1 . 121.9(2) yes C5 . C6 . C7 . 117.1(3) yes Pd1 . C6 . C7 . 121.0(2) yes C6 . C7 . C8 . 122.9(3) yes C6 . C7 . H71 . 119.4 no C8 . C7 . H71 . 117.8 no C7 . C8 . C9 . 117.2(3) yes C7 . C8 . H81 . 121.3 no C9 . C8 . H81 . 121.4 no C8 . C9 . C10 . 123.5(3) yes C8 . C9 . F11 . 119.4(3) yes C10 . C9 . F11 . 117.2(3) yes C5 . C10 . C9 . 118.7(3) yes C5 . C10 . H101 . 120.8 no C9 . C10 . H101 . 120.6 no C3 . N12 . C13 . 123.6(3) yes C3 . N12 . C14 . 119.0(3) yes C13 . N12 . C14 . 117.4(3) yes N12 . C13 . H132 . 108.1 no N12 . C13 . H131 . 111.0 no H132 . C13 . H131 . 109.2 no N12 . C13 . H133 . 110.1 no H132 . C13 . H133 . 108.9 no H131 . C13 . H133 . 109.6 no N12 . C14 . H143 . 110.0 no N12 . C14 . H141 . 110.0 no H143 . C14 . H141 . 109.5 no N12 . C14 . H142 . 110.2 no H143 . C14 . H142 . 108.7 no H141 . C14 . H142 . 108.5 no Pd1 . N15 . C16 . 165.0(3) yes N15 . C16 . C17 . 177.9(4) yes C16 . C17 . H171 . 109.4 no C16 . C17 . H172 . 110.0 no H171 . C17 . H172 . 109.3 no C16 . C17 . H173 . 108.9 no H171 . C17 . H173 . 109.4 no H172 . C17 . H173 . 109.7 no Pd1 . N18 . C19 . 166.6(3) yes N18 . C19 . C20 . 177.8(4) yes C19 . C20 . H203 . 109.9 no C19 . C20 . H201 . 109.7 no H203 . C20 . H201 . 109.2 no C19 . C20 . H202 . 109.3 no H203 . C20 . H202 . 109.7 no H201 . C20 . H202 . 109.1 no C25 . S21 . O220 . 103.8(2) yes C25 . S21 . O230 . 104.0(2) yes O220 . S21 . O230 . 106.2(3) yes C25 . S21 . O240 . 108.3(2) yes O220 . S21 . O240 . 116.0(3) yes O230 . S21 . O240 . 117.2(3) yes S21 . C25 . C26 . 120.5(3) yes S21 . C25 . C30 . 119.4(3) yes C26 . C25 . C30 . 120.1(3) yes C25 . C26 . C27 . 119.5(3) yes C25 . C26 . H261 . 119.9 no C27 . C26 . H261 . 120.6 no C26 . C27 . C28 . 121.6(3) yes C26 . C27 . H271 . 119.0 no C28 . C27 . H271 . 119.4 no C27 . C28 . C29 . 117.8(3) yes C27 . C28 . C31 . 120.3(4) yes C29 . C28 . C31 . 121.9(4) yes C28 . C29 . C30 . 121.6(4) yes C28 . C29 . H291 . 119.4 no C30 . C29 . H291 . 119.0 no C25 . C30 . C29 . 119.4(4) yes C25 . C30 . H301 . 120.2 no C29 . C30 . H301 . 120.4 no C28 . C31 . H312 . 110.2 no C28 . C31 . H311 . 110.8 no H312 . C31 . H311 . 109.0 no C28 . C31 . H313 . 109.7 no H312 . C31 . H313 . 108.6 no H311 . C31 . H313 . 108.6 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 C10 . H101 . O220 . 146 0.93 2.34 3.156(5) yes C13 . H132 . O230 3_445 173 0.96 2.50 3.457(5) yes C13 . H131 . O220 . 129 0.97 2.47 3.176(5) yes C14 . H143 . O241 3_545 136 0.95 2.46 3.214(5) yes C17 . H172 . O240 2_666 165 0.96 2.42 3.356(5) yes C17 . H173 . O231 2_566 151 0.95 2.03 2.901(5) yes C20 . H203 . O241 4_565 130 0.96 2.35 3.052(5) yes C20 . H202 . O221 2_666 148 0.95 2.42 3.264(5) yes N4 . H41 . O220 . 161 0.84 2.16 2.968(5) yes N4 . H41 . O221 . 143 0.84 2.23 2.946(5) yes