# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email AHSEN@GYTE.EDU.TR _publ_contact_author_name 'Prof Vefa Ahsen' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Chemistry Gebze Institute of Technology POB.141 Gebze 41400 TURKEY ; _publ_section_title ; Unprecedented tubular channels assemblies afford by alkyl substituted oxamide oxime metal complexes ; # 4. TEXT _publ_section_abstract ; The synthesis of an oxamide oxime substituted with hexyl chains together with its nickel(II) (1) and palladium(II) (2) complexes are described. The complexes crystallize in the rhombohedral space group R-3 (1) a=27.396(2)A, b=12.667(1)A and (2) a=27.874(2)A, b=12.410(1)A (hexagonal axes). In the crystal the complex molecules are link through hydrogen bonds involving the oximic oxygen atoms and the amino nitrogen atoms to build infinite tubular channels partly filled by the hexyl chains and self-organized in two dimensional hexagonal arrays. ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; Data were collected at room temperature (300K) with a Bruker SMART CCD diffractometer equipped with a normal focus molybdenum-target X-ray tube. The data were processed through the SAINT reduction and absorption correction softwareto give 54387 collected reflections from which 20361 are independents. The structures were solved and refined onusing the SHELXTL software. All non-hydrogen atoms were refined with anisotropic thermal parameters. The hydrogen atoms were included in the final refinement steps, in calculated position and with isotropic thermal parameters. ; _publ_section_references ; SHELXTL - Ver. 5.030 Copyright(c) 1994 Siemens Analytical X-ray Instruments ; loop_ _publ_author_name 'Vefa Ahsen' 'Gulay Gumus' 'Colette Lebrun' 'Dominique Luneau' 'Jacques Pecaut' data_gulayni _database_code_depnum_ccdc_archive 'CCDC 199677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H58 N8 Ni O4' _chemical_formula_weight 629.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.3962(16) _cell_length_b 27.3962(16) _cell_length_c 12.6672(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8233.6(9) _cell_formula_units_Z 9 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3078 _exptl_absorpt_coefficient_mu 0.570 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13959 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.90 _reflns_number_total 4275 _reflns_number_gt 2534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4275 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.224 _refine_ls_shift/su_mean 0.035 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.5000 0.5000 0.0000 0.0427(2) Uani 1 2 d S . . O1 O 0.40423(8) 0.41877(8) 0.11603(15) 0.0566(5) Uani 1 1 d . . . O2 O 0.53588(9) 0.49068(9) -0.20885(17) 0.0765(7) Uani 1 1 d . . . H2A H 0.5599 0.5225 -0.1906 0.115 Uiso 1 1 calc R . . N1 N 0.43526(9) 0.42998(9) 0.02644(17) 0.0462(6) Uani 1 1 d . . . N2 N 0.49671(9) 0.46537(10) -0.12834(18) 0.0518(6) Uani 1 1 d . . . N3 N 0.37397(10) 0.33937(10) -0.0449(2) 0.0587(7) Uani 1 1 d . . . H3A H 0.3553 0.3267 -0.1026 0.070 Uiso 1 1 calc R . . N4 N 0.44749(12) 0.37906(11) -0.2240(2) 0.0720(8) Uani 1 1 d . . . H4A H 0.4181 0.3461 -0.2199 0.086 Uiso 1 1 calc R . . C1 C 0.41961(11) 0.39227(11) -0.0475(2) 0.0454(6) Uani 1 1 d . . . C2 C 0.45711(12) 0.41364(11) -0.1414(2) 0.0499(7) Uani 1 1 d . . . C11 C 0.35418(15) 0.30275(13) 0.0453(3) 0.0745(10) Uani 1 1 d . . . H11A H 0.3242 0.2659 0.0237 0.089 Uiso 1 1 calc R . . H11B H 0.3388 0.3177 0.0966 0.089 Uiso 1 1 calc R . . C12 C 0.4015(2) 0.29685(18) 0.0966(4) 0.1103(15) Uani 1 1 d . . . H12A H 0.4161 0.2811 0.0453 0.132 Uiso 1 1 calc R . . H12B H 0.4320 0.3340 0.1154 0.132 Uiso 1 1 calc R . . C13 C 0.3839(3) 0.2613(2) 0.1908(5) 0.167(3) Uani 1 1 d . . . H13A H 0.3528 0.2243 0.1734 0.201 Uiso 1 1 calc R . . H13B H 0.3712 0.2777 0.2442 0.201 Uiso 1 1 calc R . . C14 C 0.4344(4) 0.2557(4) 0.2353(7) 0.223(5) Uani 1 1 d . . . H14A H 0.4443 0.2352 0.1854 0.267 Uiso 1 1 calc R . . H14B H 0.4671 0.2928 0.2453 0.267 Uiso 1 1 calc R . . C15 C 0.4187(6) 0.2271(7) 0.3310(10) 0.337(8) Uani 1 1 d . . . H15A H 0.4152 0.2511 0.3830 0.405 Uiso 1 1 calc R . . H15B H 0.3819 0.1938 0.3227 0.405 Uiso 1 1 calc R . . C16 C 0.4545(6) 0.2113(6) 0.3681(9) 0.317(8) Uani 1 1 d . . . H16A H 0.4402 0.1911 0.4332 0.476 Uiso 1 1 calc R . . H16B H 0.4906 0.2441 0.3803 0.476 Uiso 1 1 calc R . . H16C H 0.4583 0.1873 0.3175 0.476 Uiso 1 1 calc R . . C21 C 0.4816(2) 0.39129(17) -0.3206(3) 0.1028(16) Uani 1 1 d . . . H21A H 0.4705 0.4117 -0.3685 0.123 Uiso 1 1 calc R . . H21B H 0.5207 0.4165 -0.3018 0.123 Uiso 1 1 calc R . . C22 C 0.4790(6) 0.3498(4) -0.3710(7) 0.333(9) Uani 1 1 d . . . H22A H 0.5097 0.3666 -0.4214 0.399 Uiso 1 1 calc R . . H22B H 0.4447 0.3348 -0.4125 0.399 Uiso 1 1 calc R . . C23 C 0.4797(4) 0.3028(3) -0.3330(7) 0.207(4) Uani 1 1 d . . . H23A H 0.4472 0.2700 -0.3627 0.248 Uiso 1 1 calc R . . H23B H 0.4736 0.3016 -0.2574 0.248 Uiso 1 1 calc R . . C24 C 0.5268(4) 0.2954(4) -0.3491(8) 0.213(4) Uani 1 1 d . . . H24A H 0.5579 0.3234 -0.3074 0.255 Uiso 1 1 calc R . . H24B H 0.5377 0.3030 -0.4228 0.255 Uiso 1 1 calc R . . C25 C 0.5183(5) 0.2385(4) -0.3221(10) 0.257(5) Uani 1 1 d . . . H25A H 0.5075 0.2315 -0.2483 0.309 Uiso 1 1 calc R . . H25B H 0.4864 0.2109 -0.3628 0.309 Uiso 1 1 calc R . . C26 C 0.5607(5) 0.2284(6) -0.3367(13) 0.400(11) Uani 1 1 d . . . H26A H 0.5489 0.1903 -0.3166 0.600 Uiso 1 1 calc R . . H26B H 0.5923 0.2539 -0.2943 0.600 Uiso 1 1 calc R . . H26C H 0.5714 0.2338 -0.4098 0.600 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0398(3) 0.0397(3) 0.0419(4) -0.0059(2) 0.0065(2) 0.0149(2) O1 0.0497(11) 0.0531(11) 0.0502(12) -0.0007(9) 0.0184(9) 0.0131(9) O2 0.0755(14) 0.0624(13) 0.0551(14) -0.0118(11) 0.0283(12) 0.0072(11) N1 0.0419(12) 0.0443(12) 0.0456(15) -0.0042(10) 0.0090(10) 0.0164(10) N2 0.0506(13) 0.0473(13) 0.0443(15) -0.0063(11) 0.0111(11) 0.0146(11) N3 0.0561(14) 0.0457(13) 0.0541(17) -0.0078(12) -0.0014(12) 0.0105(11) N4 0.0818(19) 0.0545(15) 0.0565(18) -0.0165(13) 0.0128(14) 0.0168(14) C1 0.0428(14) 0.0413(14) 0.0481(17) -0.0052(12) 0.0026(12) 0.0180(12) C2 0.0543(16) 0.0487(16) 0.0445(17) -0.0086(13) 0.0015(13) 0.0241(14) C11 0.082(2) 0.0449(17) 0.073(3) -0.0021(17) 0.010(2) 0.0145(17) C12 0.147(4) 0.075(3) 0.093(3) 0.007(2) -0.017(3) 0.044(3) C13 0.268(9) 0.104(4) 0.109(5) 0.017(3) -0.024(5) 0.078(5) C14 0.344(14) 0.194(8) 0.164(8) 0.036(6) -0.069(8) 0.160(9) C15 0.330(18) 0.43(2) 0.329(18) 0.105(15) -0.033(13) 0.250(18) C16 0.45(2) 0.366(18) 0.238(13) 0.003(11) -0.074(13) 0.282(18) C21 0.146(4) 0.068(2) 0.056(3) -0.0192(19) 0.030(2) 0.025(2) C22 0.62(2) 0.269(10) 0.272(10) 0.163(9) 0.333(13) 0.340(14) C23 0.255(8) 0.171(6) 0.261(9) 0.081(6) 0.158(7) 0.157(7) C24 0.192(8) 0.214(9) 0.249(10) -0.017(7) 0.041(7) 0.114(8) C25 0.275(13) 0.208(10) 0.356(15) -0.023(10) -0.001(11) 0.171(10) C26 0.310(17) 0.45(2) 0.59(3) -0.22(2) -0.115(16) 0.303(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni N2 1.862(2) . ? Ni N2 1.862(2) 10_665 ? Ni N1 1.880(2) . ? Ni N1 1.880(2) 10_665 ? O1 N1 1.358(3) . ? O2 N2 1.389(3) . ? N1 C1 1.298(3) . ? N2 C2 1.294(3) . ? N3 C1 1.361(3) . ? N3 C11 1.436(4) . ? N4 C2 1.346(3) . ? N4 C21 1.473(4) . ? C1 C2 1.487(4) . ? C11 C12 1.530(6) . ? C12 C13 1.462(7) . ? C13 C14 1.570(10) . ? C14 C15 1.390(14) . ? C15 C16 1.339(13) . ? C21 C22 1.276(8) . ? C22 C23 1.384(9) . ? C23 C24 1.416(9) . ? C24 C25 1.496(10) . ? C25 C26 1.336(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni N2 180.00(15) . 10_665 ? N2 Ni N1 81.66(9) . . ? N2 Ni N1 98.34(9) 10_665 . ? N2 Ni N1 98.34(9) . 10_665 ? N2 Ni N1 81.66(9) 10_665 10_665 ? N1 Ni N1 180.00(18) . 10_665 ? C1 N1 O1 120.2(2) . . ? C1 N1 Ni 116.83(18) . . ? O1 N1 Ni 122.97(16) . . ? C2 N2 O2 117.9(2) . . ? C2 N2 Ni 118.03(19) . . ? O2 N2 Ni 123.94(17) . . ? C1 N3 C11 126.0(3) . . ? C2 N4 C21 127.4(3) . . ? N1 C1 N3 126.3(2) . . ? N1 C1 C2 112.0(2) . . ? N3 C1 C2 121.6(2) . . ? N2 C2 N4 129.2(3) . . ? N2 C2 C1 111.4(2) . . ? N4 C2 C1 119.4(2) . . ? N3 C11 C12 111.6(3) . . ? C13 C12 C11 113.8(5) . . ? C12 C13 C14 110.2(7) . . ? C15 C14 C13 109.2(10) . . ? C16 C15 C14 114.7(14) . . ? C22 C21 N4 117.8(5) . . ? C21 C22 C23 129.4(10) . . ? C22 C23 C24 121.3(8) . . ? C23 C24 C25 115.9(9) . . ? C26 C25 C24 119.0(12) . . ? _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 28.90 _diffrn_measured_fraction_theta_full 0.885 _refine_diff_density_max 0.782 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.147 #===END data_gulaypd _database_code_depnum_ccdc_archive 'CCDC 199678' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H58 N8 O4 Pd' _chemical_formula_weight 677.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.8737(19) _cell_length_b 27.8737(19) _cell_length_c 12.4102(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8350.2(12) _cell_formula_units_Z 9 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3240 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11101 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.1911 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 29.60 _reflns_number_total 4622 _reflns_number_gt 1752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4622 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1684 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 0.651 _refine_ls_restrained_S_all 0.651 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd Pd 0.5000 0.5000 0.0000 0.0527(2) Uani 1 2 d S . . O1 O 0.41985(11) 0.40604(11) -0.1238(2) 0.0673(9) Uani 1 1 d . . . O2 O 0.48357(13) 0.53195(13) 0.2173(3) 0.0861(11) Uani 1 1 d . . . H2A H 0.5153 0.5553 0.2006 0.129 Uiso 1 1 calc R . . N1 N 0.42778(14) 0.43370(14) -0.0309(3) 0.0571(9) Uani 1 1 d . . . N2 N 0.45978(15) 0.49367(15) 0.1341(3) 0.0633(10) Uani 1 1 d . . . N3 N 0.33765(15) 0.37353(15) 0.0368(3) 0.0725(11) Uani 1 1 d . . . H3A H 0.3243 0.3539 0.0940 0.087 Uiso 1 1 calc R . . N4 N 0.37283(17) 0.44209(18) 0.2233(3) 0.0853(13) Uani 1 1 d . . . H4A H 0.3401 0.4142 0.2144 0.102 Uiso 1 1 calc R . . C1 C 0.38989(18) 0.41851(17) 0.0436(4) 0.0579(12) Uani 1 1 d . . . C2 C 0.40885(19) 0.45390(19) 0.1415(4) 0.0603(12) Uani 1 1 d . . . C11 C 0.3032(2) 0.3563(3) -0.0571(5) 0.099(2) Uani 1 1 d . . . H11A H 0.2670 0.3255 -0.0386 0.119 Uiso 1 1 calc R . . H11B H 0.3193 0.3435 -0.1112 0.119 Uiso 1 1 calc R . . C12 C 0.2967(3) 0.4033(3) -0.1034(7) 0.143(3) Uani 1 1 d . . . H12A H 0.2821 0.4165 -0.0472 0.172 Uiso 1 1 calc R . . H12B H 0.3333 0.4335 -0.1216 0.172 Uiso 1 1 calc R . . C13 C 0.2622(4) 0.3908(5) -0.1962(9) 0.216(5) Uani 1 1 d . . . H13A H 0.2255 0.3608 -0.1781 0.259 Uiso 1 1 calc R . . H13B H 0.2767 0.3774 -0.2525 0.259 Uiso 1 1 calc R . . C14 C 0.2565(6) 0.4389(7) -0.2419(12) 0.266(8) Uani 1 1 d . . . H14A H 0.2390 0.4509 -0.1892 0.319 Uiso 1 1 calc R . . H14B H 0.2928 0.4700 -0.2583 0.319 Uiso 1 1 calc R . . C15 C 0.2251(13) 0.4215(10) -0.333(2) 0.408(17) Uani 1 1 d . . . H15A H 0.2463 0.4161 -0.3892 0.490 Uiso 1 1 calc R . . H15B H 0.1926 0.3859 -0.3190 0.490 Uiso 1 1 calc R . . C16 C 0.2103(11) 0.4527(11) -0.3668(17) 0.372(14) Uani 1 1 d . . . H16A H 0.1887 0.4375 -0.4310 0.558 Uiso 1 1 calc R . . H16B H 0.2422 0.4879 -0.3831 0.558 Uiso 1 1 calc R . . H16C H 0.1882 0.4575 -0.3131 0.558 Uiso 1 1 calc R . . C21 C 0.3835(3) 0.4717(3) 0.3254(5) 0.125(3) Uani 1 1 d . . . H21A H 0.3828 0.4470 0.3813 0.150 Uiso 1 1 calc R . . H21B H 0.4211 0.5027 0.3223 0.150 Uiso 1 1 calc R . . C22 C 0.3542(6) 0.4900(7) 0.3561(11) 0.359(13) Uani 1 1 d . . . H22A H 0.3788 0.5298 0.3553 0.431 Uiso 1 1 calc R . . H22B H 0.3480 0.4797 0.4316 0.431 Uiso 1 1 calc R . . C23 C 0.3040(4) 0.4832(4) 0.3215(9) 0.199(4) Uani 1 1 d . . . H23A H 0.2745 0.4502 0.3552 0.239 Uiso 1 1 calc R . . H23B H 0.3012 0.4768 0.2444 0.239 Uiso 1 1 calc R . . C24 C 0.2939(5) 0.5298(5) 0.3437(12) 0.236(6) Uani 1 1 d . . . H24A H 0.3203 0.5618 0.3026 0.283 Uiso 1 1 calc R . . H24B H 0.3008 0.5393 0.4195 0.283 Uiso 1 1 calc R . . C25 C 0.2385(6) 0.5182(6) 0.3176(13) 0.260(7) Uani 1 1 d . . . H25A H 0.2312 0.5074 0.2425 0.312 Uiso 1 1 calc R . . H25B H 0.2123 0.4869 0.3605 0.312 Uiso 1 1 calc R . . C26 C 0.2288(7) 0.5626(6) 0.3349(15) 0.378(12) Uani 1 1 d . . . H26A H 0.1913 0.5514 0.3154 0.568 Uiso 1 1 calc R . . H26B H 0.2538 0.5936 0.2914 0.568 Uiso 1 1 calc R . . H26C H 0.2346 0.5729 0.4095 0.568 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd 0.0444(3) 0.0435(3) 0.0639(4) -0.0086(2) 0.0067(2) 0.0174(2) O1 0.0583(19) 0.0524(18) 0.078(2) -0.0215(17) 0.0032(16) 0.0177(16) O2 0.070(2) 0.076(2) 0.084(3) -0.031(2) 0.0118(18) 0.0154(18) N1 0.050(2) 0.047(2) 0.069(3) -0.008(2) 0.005(2) 0.0197(18) N2 0.052(2) 0.055(2) 0.068(3) -0.016(2) 0.004(2) 0.016(2) N3 0.053(3) 0.059(3) 0.085(3) 0.004(2) 0.009(2) 0.013(2) N4 0.062(3) 0.092(3) 0.078(3) -0.015(3) 0.017(2) 0.021(2) C1 0.050(3) 0.046(3) 0.075(3) -0.003(2) 0.007(3) 0.022(2) C2 0.056(3) 0.057(3) 0.070(3) -0.005(3) 0.010(3) 0.030(3) C11 0.058(4) 0.104(5) 0.103(5) -0.013(4) -0.004(3) 0.017(3) C12 0.088(5) 0.159(8) 0.160(8) 0.029(6) -0.020(5) 0.045(5) C13 0.123(8) 0.294(15) 0.196(10) 0.032(10) -0.033(7) 0.078(9) C14 0.235(14) 0.36(2) 0.225(14) 0.069(14) -0.067(11) 0.164(14) C15 0.52(4) 0.32(3) 0.36(3) 0.00(2) -0.21(3) 0.19(3) C16 0.45(3) 0.49(4) 0.27(2) 0.02(2) -0.056(19) 0.30(3) C21 0.078(4) 0.186(8) 0.072(5) -0.019(5) 0.029(3) 0.037(5) C22 0.288(16) 0.61(3) 0.356(19) -0.36(2) -0.199(15) 0.35(2) C23 0.153(8) 0.207(10) 0.277(12) -0.100(9) -0.050(8) 0.119(8) C24 0.174(11) 0.181(10) 0.358(18) -0.064(11) 0.011(11) 0.093(10) C25 0.223(15) 0.244(15) 0.358(19) -0.037(13) 0.026(13) 0.150(13) C26 0.47(3) 0.33(2) 0.51(3) 0.081(19) 0.16(2) 0.33(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd N2 1.965(4) . ? Pd N2 1.965(4) 10_665 ? Pd N1 1.973(3) . ? Pd N1 1.973(3) 10_665 ? O1 N1 1.342(4) . ? O2 N2 1.391(4) . ? N1 C1 1.305(5) . ? N2 C2 1.296(5) . ? N3 C1 1.369(5) . ? N3 C11 1.431(7) . ? N4 C2 1.348(5) . ? N4 C21 1.460(7) . ? C1 C2 1.485(6) . ? C11 C12 1.521(9) . ? C12 C13 1.429(11) . ? C13 C14 1.535(15) . ? C14 C15 1.36(2) . ? C15 C16 1.21(2) . ? C21 C22 1.219(11) . ? C22 C23 1.385(11) . ? C23 C24 1.483(12) . ? C24 C25 1.448(14) . ? C25 C26 1.408(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Pd N2 180.0(2) . 10_665 ? N2 Pd N1 79.14(15) . . ? N2 Pd N1 100.86(15) 10_665 . ? N2 Pd N1 100.86(15) . 10_665 ? N2 Pd N1 79.14(15) 10_665 10_665 ? N1 Pd N1 180.000(1) . 10_665 ? C1 N1 O1 123.2(3) . . ? C1 N1 Pd 116.6(3) . . ? O1 N1 Pd 120.2(3) . . ? C2 N2 O2 120.1(4) . . ? C2 N2 Pd 117.9(3) . . ? O2 N2 Pd 121.9(3) . . ? C1 N3 C11 125.9(4) . . ? C2 N4 C21 126.8(4) . . ? N1 C1 N3 124.8(4) . . ? N1 C1 C2 113.7(4) . . ? N3 C1 C2 121.4(4) . . ? N2 C2 N4 128.7(4) . . ? N2 C2 C1 112.6(4) . . ? N4 C2 C1 118.6(4) . . ? N3 C11 C12 111.5(6) . . ? C13 C12 C11 116.8(9) . . ? C12 C13 C14 115.9(11) . . ? C15 C14 C13 109.0(18) . . ? C16 C15 C14 115(3) . . ? C22 C21 N4 121.2(8) . . ? C21 C22 C23 133.6(10) . . ? C22 C23 C24 116.4(11) . . ? C23 C24 C25 114.2(11) . . ? C26 C25 C24 115.0(14) . . ? _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 29.60 _diffrn_measured_fraction_theta_full 0.885 _refine_diff_density_max 0.823 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.152