#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2214482.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2214482 loop_ _publ_author_name 'Sui, Yan' 'Li, Xin-Fa' 'Huang, Gan-Sheng' 'Wang, Gui-Juan' _publ_section_title ; {\m-6,6'-Diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}trinitratopraseodymium(III)nickel(II) ; _journal_coeditor_code AT2333 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m2093 _journal_page_last m2094 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac '[Ni Pr (C20 H22 N2 O4) (N O3)3]' _chemical_formula_moiety 'C20 H22 N5 Ni O13 Pr' _chemical_formula_sum 'C20 H22 N5 Ni O13 Pr' _chemical_formula_weight 740.05 _chemical_name_systematic ; {6,6'-diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-\ 1\k^4^O^1^,O^1'^,O^6^,O^6'^:2\k^4^O^1^,\ N,N',O^1'^}trinitrato-1\k^6^O,O'-\ praseodymium(III)nickel(II)) ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6317(7) _cell_length_b 13.8782(11) _cell_length_c 21.1267(16) _cell_measurement_reflns_used 19198 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.23 _cell_measurement_theta_min 1.93 _cell_volume 2530.8(3) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction APEX2 _computing_molecular_graphics APEX2 _computing_publication_material 'APEX2 and publCIF (Westrip, 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 0 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker APEXII area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 19198 _diffrn_reflns_theta_full 28.23 _diffrn_reflns_theta_max 28.23 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.724 _exptl_absorpt_correction_T_max 0.7184 _exptl_absorpt_correction_T_min 0.5856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2004)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1472 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.494 _refine_diff_density_min -0.945 _refine_ls_abs_structure_details 'Flack (1983), 2527 Freidel pairs' _refine_ls_abs_structure_Flack -0.029(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 6058 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0284 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.0643 _reflns_number_gt 4803 _reflns_number_total 6058 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file at2333.cif _[local]_cod_data_source_block I _cod_database_code 2214482 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O7 0.9049(4) 1.0768(3) 0.27827(16) 0.0824(12) Uani d . 1 O O10 1.2400(4) 1.0390(4) 0.0732(2) 0.0940(13) Uani d . 1 O O13 0.5733(5) 1.0011(3) -0.08811(14) 0.0778(9) Uani d . 1 O O1 0.5857(3) 0.87476(17) 0.13660(13) 0.0400(6) Uani d . 1 Pr Pr1 0.75873(2) 0.999679(15) 0.094894(9) 0.03254(6) Uani d . 1 Ni Ni1 0.43318(5) 0.94379(3) 0.18298(2) 0.03345(11) Uani d . 1 O O2 0.5375(3) 1.05625(18) 0.15415(12) 0.0370(6) Uani d . 1 C C16 0.4776(4) 1.1446(2) 0.15618(18) 0.0335(8) Uani d . 1 N N2 0.3003(4) 1.0132(3) 0.23914(15) 0.0413(8) Uani d . 1 C C2 0.7085(4) 0.7431(3) 0.08984(18) 0.0346(8) Uani d . 1 N N1 0.3205(4) 0.8321(2) 0.20893(16) 0.0386(8) Uani d . 1 O O3 0.8107(3) 0.81360(18) 0.06952(13) 0.0390(6) Uani d . 1 C C1 0.5858(5) 0.7798(3) 0.12641(19) 0.0350(9) Uani d . 1 C C15 0.5384(4) 1.2127(3) 0.11356(19) 0.0357(9) Uani d . 1 O O4 0.6541(3) 1.17618(17) 0.07522(13) 0.0379(6) Uani d . 1 C C10 0.2788(4) 1.1051(3) 0.23934(19) 0.0409(9) Uani d . 1 H H10 0.2096 1.1305 0.2687 0.049 Uiso calc R 1 C C11 0.3559(5) 1.1717(3) 0.1965(2) 0.0397(10) Uani d . 1 C C6 0.4755(5) 0.7163(3) 0.15066(19) 0.0385(9) Uani d . 1 C C8 0.1866(5) 0.8550(3) 0.2490(2) 0.0469(11) Uani d . 1 H H8A 0.1683 0.8033 0.2790 0.056 Uiso calc R 1 H H8B 0.0946 0.8629 0.2232 0.056 Uiso calc R 1 C C7 0.3494(5) 0.7458(3) 0.1916(2) 0.0418(10) Uani d . 1 H H7 0.2839 0.6978 0.2066 0.050 Uiso calc R 1 C C9 0.2229(5) 0.9480(3) 0.28394(19) 0.0455(9) Uani d . 1 H H9A 0.1281 0.9771 0.2995 0.055 Uiso calc R 1 H H9B 0.2900 0.9350 0.3198 0.055 Uiso calc R 1 O O11 0.7686(3) 1.0124(2) -0.02366(14) 0.0567(8) Uani d . 1 N N5 0.6275(4) 0.9943(3) -0.03484(17) 0.0509(8) Uani d . 1 O O6 0.8208(4) 0.9677(2) 0.21260(15) 0.0558(9) Uani d . 1 O O5 0.8644(3) 1.1119(2) 0.18023(16) 0.0535(7) Uani d . 1 O O8 1.0055(4) 1.0815(3) 0.04986(17) 0.0672(10) Uani d . 1 O O9 1.0438(3) 0.9620(2) 0.11169(16) 0.0580(8) Uani d . 1 O O12 0.5474(4) 0.9686(2) 0.01221(14) 0.0615(9) Uani d . 1 N N3 0.8635(4) 1.0513(3) 0.22533(19) 0.0508(9) Uani d . 1 N N4 1.1002(4) 1.0287(3) 0.07769(19) 0.0554(11) Uani d . 1 C C3 0.7179(5) 0.6468(3) 0.0751(2) 0.0452(10) Uani d . 1 H H3 0.7996 0.6234 0.0509 0.054 Uiso calc R 1 C C17 0.7260(5) 1.2411(3) 0.02947(19) 0.0445(10) Uani d . 1 H H17A 0.6465 1.2804 0.0099 0.053 Uiso calc R 1 H H17B 0.7751 1.2033 -0.0035 0.053 Uiso calc R 1 C C19 0.9471(5) 0.7816(3) 0.0349(2) 0.0462(10) Uani d . 1 H H19A 0.9904 0.8356 0.0117 0.055 Uiso calc R 1 H H19B 0.9170 0.7327 0.0045 0.055 Uiso calc R 1 C C4 0.6025(5) 0.5846(3) 0.0972(2) 0.0524(11) Uani d . 1 H H4 0.6063 0.5197 0.0865 0.063 Uiso calc R 1 C C5 0.4853(5) 0.6174(3) 0.1340(2) 0.0462(10) Uani d . 1 H H5 0.4103 0.5747 0.1485 0.055 Uiso calc R 1 C C20 1.0682(5) 0.7411(3) 0.0783(2) 0.0605(13) Uani d . 1 H H20A 1.0980 0.7892 0.1086 0.091 Uiso calc R 1 H H20B 1.1571 0.7220 0.0540 0.091 Uiso calc R 1 H H20C 1.0271 0.6860 0.1001 0.091 Uiso calc R 1 C C14 0.4812(5) 1.3050(3) 0.1115(2) 0.0434(10) Uani d . 1 H H14 0.5215 1.3495 0.0829 0.052 Uiso calc R 1 C C12 0.3023(5) 1.2675(3) 0.1951(2) 0.0494(12) Uani d . 1 H H12 0.2260 1.2872 0.2234 0.059 Uiso calc R 1 C C13 0.3612(5) 1.3314(3) 0.1529(2) 0.0521(12) Uani d . 1 H H13 0.3215 1.3937 0.1514 0.063 Uiso calc R 1 C C18 0.8450(5) 1.3056(3) 0.0597(2) 0.0584(13) Uani d . 1 H H18A 0.7959 1.3454 0.0910 0.088 Uiso calc R 1 H H18B 0.8914 1.3457 0.0279 0.088 Uiso calc R 1 H H18C 0.9235 1.2670 0.0794 0.088 Uiso calc R 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O7 0.090(3) 0.111(3) 0.0456(18) 0.047(2) -0.020(2) -0.024(2) O10 0.0355(18) 0.136(4) 0.111(3) -0.019(2) 0.003(2) 0.005(3) O13 0.107(3) 0.076(2) 0.0507(19) -0.006(2) -0.0241(19) 0.000(2) O1 0.0453(16) 0.0226(13) 0.0522(17) -0.0030(11) 0.0151(14) 0.0004(12) Pr1 0.03262(9) 0.02703(9) 0.03797(10) -0.00125(11) 0.00380(9) 0.00237(10) Ni1 0.0331(2) 0.0257(2) 0.0415(2) -0.00120(19) 0.0100(2) 0.0037(2) O2 0.0360(14) 0.0270(13) 0.0481(15) 0.0025(11) 0.0063(12) 0.0024(13) C16 0.035(2) 0.0254(18) 0.040(2) -0.0005(14) -0.0053(17) 0.0018(16) N2 0.0403(15) 0.047(2) 0.0362(17) -0.0028(15) 0.0060(13) 0.0048(16) C2 0.039(2) 0.0304(19) 0.034(2) -0.0007(14) -0.0049(18) 0.0029(16) N1 0.0376(18) 0.0369(19) 0.041(2) -0.0055(14) 0.0047(16) 0.0091(16) O3 0.0381(14) 0.0321(15) 0.0470(17) 0.0025(11) 0.0101(13) -0.0006(12) C1 0.039(2) 0.0278(19) 0.038(2) -0.0009(16) -0.0064(19) 0.0002(17) C15 0.034(2) 0.032(2) 0.041(2) -0.0006(15) -0.0024(18) -0.0022(17) O4 0.0446(15) 0.0262(14) 0.0430(16) -0.0018(11) 0.0062(13) 0.0079(12) C10 0.039(2) 0.044(2) 0.040(2) 0.0068(18) 0.0054(18) 0.0026(18) C11 0.038(2) 0.038(2) 0.044(3) 0.0036(16) 0.0011(19) 0.0022(19) C6 0.046(2) 0.030(2) 0.040(2) -0.0042(16) -0.0066(19) 0.0039(18) C8 0.038(2) 0.053(3) 0.049(3) -0.0039(18) 0.014(2) 0.012(2) C7 0.040(2) 0.039(2) 0.046(3) -0.0090(17) 0.000(2) 0.013(2) C9 0.043(2) 0.048(2) 0.046(2) -0.0003(19) 0.0116(19) 0.012(2) O11 0.0582(19) 0.064(2) 0.0482(16) -0.0133(18) 0.0061(14) 0.0024(14) N5 0.066(2) 0.0401(19) 0.046(2) 0.002(2) -0.0013(18) -0.009(2) O6 0.062(2) 0.059(2) 0.0460(18) 0.0054(16) 0.0048(16) 0.0144(15) O5 0.0565(18) 0.0494(17) 0.0546(19) 0.0014(14) -0.0069(17) -0.0058(17) O8 0.0465(19) 0.081(3) 0.074(2) -0.0140(16) -0.0007(17) 0.031(2) O9 0.0447(17) 0.0463(17) 0.083(2) 0.0006(14) 0.0058(17) 0.0058(16) O12 0.0528(18) 0.080(3) 0.0517(18) -0.0097(16) 0.0012(16) -0.0041(16) N3 0.041(2) 0.067(3) 0.045(2) 0.023(2) -0.0022(18) -0.006(2) N4 0.041(2) 0.068(3) 0.057(2) -0.0100(18) 0.0071(19) -0.013(2) C3 0.059(3) 0.032(2) 0.045(2) 0.0056(18) 0.000(2) -0.0027(17) C17 0.057(3) 0.036(2) 0.041(2) -0.0040(18) 0.009(2) 0.0077(17) C19 0.042(2) 0.043(2) 0.053(3) 0.0039(18) 0.007(2) -0.006(2) C4 0.069(3) 0.027(2) 0.061(3) -0.0009(18) -0.007(3) 0.000(2) C5 0.058(3) 0.026(2) 0.055(3) -0.0094(17) -0.001(2) 0.0054(19) C20 0.049(3) 0.051(3) 0.081(4) 0.010(2) -0.004(3) -0.009(2) C14 0.047(2) 0.033(2) 0.050(3) 0.0005(16) -0.005(2) 0.0065(19) C12 0.051(3) 0.037(2) 0.060(3) 0.0114(18) 0.007(2) -0.007(2) C13 0.061(3) 0.027(2) 0.068(3) 0.0093(19) 0.001(2) 0.002(2) C18 0.059(3) 0.041(3) 0.075(3) -0.010(2) 0.021(3) -0.003(2) 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' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 Ni1 125.5(2) C1 O1 Pr1 129.8(2) Ni1 O1 Pr1 104.52(10) O2 Pr1 O1 64.02(8) O2 Pr1 O11 121.39(9) O1 Pr1 O11 115.38(10) O2 Pr1 O9 139.51(9) O1 Pr1 O9 113.22(10) O11 Pr1 O9 96.94(10) O2 Pr1 O5 73.61(9) O1 Pr1 O5 113.30(9) O11 Pr1 O5 130.50(10) O9 Pr1 O5 71.38(10) O2 Pr1 O12 81.09(10) O1 Pr1 O12 72.09(10) O11 Pr1 O12 49.93(9) O9 Pr1 O12 138.61(10) O5 Pr1 O12 147.03(10) O2 Pr1 O6 73.78(9) O1 Pr1 O6 70.04(10) O11 Pr1 O6 164.82(10) O9 Pr1 O6 68.24(10) O5 Pr1 O6 49.49(10) O12 Pr1 O6 140.83(10) O2 Pr1 O8 134.21(11) O1 Pr1 O8 160.24(10) O11 Pr1 O8 64.90(10) O9 Pr1 O8 49.15(10) O5 Pr1 O8 72.45(11) O12 Pr1 O8 114.09(10) O6 Pr1 O8 104.95(11) O2 Pr1 O4 60.66(8) O1 Pr1 O4 120.23(8) O11 Pr1 O4 77.87(9) O9 Pr1 O4 122.93(9) O5 Pr1 O4 70.57(9) O12 Pr1 O4 78.77(10) O6 Pr1 O4 112.44(9) O8 Pr1 O4 79.49(10) O2 Pr1 O3 123.39(8) O1 Pr1 O3 59.45(8) O11 Pr1 O3 82.09(9) O9 Pr1 O3 70.55(9) O5 Pr1 O3 132.15(9) O12 Pr1 O3 79.66(10) O6 Pr1 O3 89.55(10) O8 Pr1 O3 102.19(10) O4 Pr1 O3 156.95(10) O1 Ni1 O2 85.44(11) O1 Ni1 N1 95.25(13) O2 Ni1 N1 177.17(13) O1 Ni1 N2 171.95(13) O2 Ni1 N2 93.96(12) N1 Ni1 N2 85.74(15) C16 O2 Ni1 124.2(2) C16 O2 Pr1 128.6(2) Ni1 O2 Pr1 105.88(11) O2 C16 C11 123.8(3) O2 C16 C15 116.9(3) C11 C16 C15 119.2(3) C10 N2 C9 122.8(3) C10 N2 Ni1 126.0(3) C9 N2 Ni1 111.2(3) C3 C2 O3 125.4(4) C3 C2 C1 121.4(4) O3 C2 C1 113.2(3) C7 N1 C8 121.5(4) C7 N1 Ni1 125.4(3) C8 N1 Ni1 113.0(3) C2 O3 C19 117.1(3) C2 O3 Pr1 120.8(2) C19 O3 Pr1 122.1(2) O1 C1 C6 124.3(4) O1 C1 C2 116.5(3) C6 C1 C2 119.1(3) C14 C15 O4 125.7(4) C14 C15 C16 120.9(4) O4 C15 C16 113.5(3) C15 O4 C17 118.0(3) C15 O4 Pr1 119.6(2) C17 O4 Pr1 122.0(2) N2 C10 C11 124.1(4) N2 C10 H10 118.0 C11 C10 H10 118.0 C16 C11 C12 119.0(4) C16 C11 C10 123.4(3) C12 C11 C10 117.6(4) C1 C6 C5 118.6(4) C1 C6 C7 123.5(3) C5 C6 C7 117.8(4) N1 C8 C9 107.6(3) N1 C8 H8A 110.2 C9 C8 H8A 110.2 N1 C8 H8B 110.2 C9 C8 H8B 110.2 H8A C8 H8B 108.5 N1 C7 C6 125.6(4) N1 C7 H7 117.2 C6 C7 H7 117.2 N2 C9 C8 107.7(3) N2 C9 H9A 110.2 C8 C9 H9A 110.2 N2 C9 H9B 110.2 C8 C9 H9B 110.2 H9A C9 H9B 108.5 N5 O11 Pr1 98.0(2) O13 N5 O12 122.5(4) O13 N5 O11 121.6(4) O12 N5 O11 115.8(3) N3 O6 Pr1 96.2(3) N3 O5 Pr1 97.1(3) N4 O8 Pr1 96.2(2) N4 O9 Pr1 98.2(2) N5 O12 Pr1 95.7(2) O7 N3 O6 123.4(5) O7 N3 O5 119.4(5) O6 N3 O5 117.1(4) O10 N4 O8 123.0(4) O10 N4 O9 120.6(5) O8 N4 O9 116.4(3) C2 C3 C4 118.9(4) C2 C3 H3 120.6 C4 C3 H3 120.6 O4 C17 C18 112.1(3) O4 C17 H17A 109.2 C18 C17 H17A 109.2 O4 C17 H17B 109.2 C18 C17 H17B 109.2 H17A C17 H17B 107.9 O3 C19 C20 111.8(4) O3 C19 H19A 109.3 C20 C19 H19A 109.3 O3 C19 H19B 109.3 C20 C19 H19B 109.3 H19A C19 H19B 107.9 C5 C4 C3 121.1(4) C5 C4 H4 119.5 C3 C4 H4 119.5 C4 C5 C6 120.8(4) C4 C5 H5 119.6 C6 C5 H5 119.6 C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C15 C14 C13 119.2(4) C15 C14 H14 120.4 C13 C14 H14 120.4 C13 C12 C11 120.5(4) C13 C12 H12 119.7 C11 C12 H12 119.7 C12 C13 C14 121.0(4) C12 C13 H13 119.5 C14 C13 H13 119.5 C17 C18 H18A 109.5 C17 C18 H18B 109.5 H18A C18 H18B 109.5 C17 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O7 N3 1.226(5) ? O10 N4 1.218(4) ? O13 N5 1.222(4) ? O1 C1 1.335(4) ? O1 Ni1 1.900(3) y O1 Pr1 2.452(2) y Pr1 O2 2.415(2) y Pr1 O3 2.675(3) y Pr1 O4 2.644(2) y Pr1 O5 2.551(3) y Pr1 O6 2.582(3) y Pr1 O8 2.595(3) y Pr1 O9 2.541(3) y Pr1 O11 2.512(3) y Pr1 O12 2.562(3) y Ni1 O2 1.902(3) y Ni1 N1 1.910(3) y Ni1 N2 1.911(3) y O2 C16 1.332(4) ? C16 C11 1.404(5) ? C16 C15 1.407(5) ? N2 C10 1.289(5) ? N2 C9 1.471(5) ? C2 C3 1.374(5) ? C2 O3 1.386(4) ? C2 C1 1.406(5) ? N1 C7 1.276(5) ? N1 C8 1.468(5) ? O3 C19 1.456(5) ? C1 C6 1.396(5) ? C15 C14 1.374(5) ? C15 O4 1.382(4) ? O4 C17 1.460(4) ? C10 C11 1.454(5) ? C10 H10 0.9300 ? C11 C12 1.409(6) ? C6 C5 1.419(5) ? C6 C7 1.450(6) ? C8 C9 1.519(6) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C7 H7 0.9300 ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? O11 N5 1.266(4) ? N5 O12 1.262(4) ? O6 N3 1.248(5) ? O5 N3 1.271(5) ? O8 N4 1.245(5) ? O9 N4 1.268(5) ? C3 C4 1.398(6) ? C3 H3 0.9300 ? C17 C18 1.505(6) ? C17 H17A 0.9700 ? C17 H17B 0.9700 ? C19 C20 1.500(6) ? C19 H19A 0.9700 ? C19 H19B 0.9700 ? C4 C5 1.354(6) ? C4 H4 0.9300 ? C5 H5 0.9300 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? C14 C13 1.405(6) ? C14 H14 0.9300 ? C12 C13 1.357(6) ? C12 H12 0.9300 ? C13 H13 0.9300 ? C18 H18A 0.9600 ? C18 H18B 0.9600 ? C18 H18C 0.9600 ? 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 C20 H20A O9 . 0.96 2.44 3.154(5) 130.5 C17 H17A O8 4_475 0.97 2.60 3.535(5) 162.6 C9 H9A O7 1_455 0.97 2.41 3.278(5) 148.1 C7 H7 O7 3_645 0.93 2.36 3.275(5) 167.3