# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bh326wh1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C72 H106 N4 Ni2 O4, 4(C6 D6)' _chemical_formula_sum 'C96 H106 D24 N4 Ni2 O4' _chemical_formula_weight 1545.26 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.3703(7) _cell_length_b 22.7046(6) _cell_length_c 10.8435(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.275(3) _cell_angle_gamma 90.00 _cell_volume 4258.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 26222 _cell_measurement_theta_min 2.09 _cell_measurement_theta_max 27.10 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1644 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8577 _exptl_absorpt_correction_T_max 0.9522 _exptl_absorpt_process_details 'Spek, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'STOE IPDS2theta' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 30295 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.84 _reflns_number_total 8989 _reflns_number_gt 7077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, 1990' _computing_publication_material 'PLATON, 1990' _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^)+(0.0353P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8989 _refine_ls_number_parameters 492 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _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 Ni1 Ni 0.356706(9) 0.005745(7) 0.054998(17) 0.01065(5) Uani 1 1 d . . . O1 O 0.46315(5) 0.00100(4) 0.14375(9) 0.0150(2) Uani 1 1 d . . . O2 O 0.58576(5) -0.00243(4) 0.09559(9) 0.0137(2) Uani 1 1 d . . . N1 N 0.27379(6) -0.04847(5) 0.06146(11) 0.0103(2) Uani 1 1 d . . . N2 N 0.29993(6) 0.07620(5) 0.07982(11) 0.0112(2) Uani 1 1 d . . . C1 C 0.51407(7) -0.00032(6) 0.06881(13) 0.0119(3) Uani 1 1 d . . . C2 C 0.30425(7) -0.10739(6) 0.06554(14) 0.0114(3) Uani 1 1 d . . . C3 C 0.31640(8) -0.13715(6) -0.04521(14) 0.0144(3) Uani 1 1 d . . . C4 C 0.34705(9) -0.19372(6) -0.03618(16) 0.0204(3) Uani 1 1 d . . . H4 H 0.3537 -0.2145 -0.1083 0.024 Uiso 1 1 calc R . . C5 C 0.36782(9) -0.21985(6) 0.07677(16) 0.0223(4) Uani 1 1 d . . . H5 H 0.3873 -0.2580 0.0805 0.027 Uiso 1 1 calc R . . C6 C 0.35940(8) -0.18893(6) 0.18421(15) 0.0195(3) Uani 1 1 d . . . H6 H 0.3750 -0.2062 0.2602 0.023 Uiso 1 1 calc R . . C7 C 0.32810(8) -0.13235(6) 0.18156(14) 0.0143(3) Uani 1 1 d . . . C8 C 0.32073(8) -0.10086(6) 0.30380(14) 0.0172(3) Uani 1 1 d . . . H8 H 0.2967 -0.0624 0.2856 0.021 Uiso 1 1 calc R . . C9 C 0.40059(9) -0.09050(7) 0.37251(16) 0.0234(3) Uani 1 1 d . . . H9A H 0.4253 -0.1277 0.3908 0.035 Uiso 1 1 calc R . . H9B H 0.3950 -0.0697 0.4483 0.035 Uiso 1 1 calc R . . H9C H 0.4316 -0.0676 0.3215 0.035 Uiso 1 1 calc R . . C10 C 0.26981(9) -0.13496(7) 0.38725(16) 0.0233(3) Uani 1 1 d . . . H10A H 0.2194 -0.1406 0.3446 0.035 Uiso 1 1 calc R . . H10B H 0.2653 -0.1131 0.4620 0.035 Uiso 1 1 calc R . . H10C H 0.2928 -0.1726 0.4075 0.035 Uiso 1 1 calc R . . C11 C 0.29720(8) -0.11063(6) -0.17287(14) 0.0177(3) Uani 1 1 d . . . H11 H 0.2831 -0.0693 -0.1624 0.021 Uiso 1 1 calc R . . C12 C 0.36711(9) -0.11277(7) -0.24955(16) 0.0218(3) Uani 1 1 d . . . H12A H 0.4117 -0.0972 -0.2015 0.033 Uiso 1 1 calc R . . H12B H 0.3566 -0.0896 -0.3232 0.033 Uiso 1 1 calc R . . H12C H 0.3768 -0.1528 -0.2719 0.033 Uiso 1 1 calc R . . C13 C 0.22917(9) -0.14164(8) -0.24620(16) 0.0267(4) Uani 1 1 d . . . H13A H 0.2425 -0.1820 -0.2598 0.040 Uiso 1 1 calc R . . H13B H 0.2179 -0.1223 -0.3245 0.040 Uiso 1 1 calc R . . H13C H 0.1846 -0.1400 -0.2002 0.040 Uiso 1 1 calc R . . C14 C 0.20023(7) -0.03314(6) 0.07036(13) 0.0112(3) Uani 1 1 d . . . C15 C 0.17961(8) 0.02643(6) 0.07801(14) 0.0130(3) Uani 1 1 d . . . H15 H 0.1267 0.0327 0.0779 0.016 Uiso 1 1 calc R . . C16 C 0.22372(7) 0.07835(6) 0.08577(13) 0.0116(3) Uani 1 1 d . . . C17 C 0.35327(7) 0.12479(6) 0.09750(14) 0.0120(3) Uani 1 1 d . . . C18 C 0.38041(8) 0.15186(6) -0.00739(14) 0.0139(3) Uani 1 1 d . . . C19 C 0.43461(8) 0.19714(6) 0.01294(15) 0.0184(3) Uani 1 1 d . . . H19 H 0.4527 0.2160 -0.0548 0.022 Uiso 1 1 calc R . . C20 C 0.46185(8) 0.21447(6) 0.13056(16) 0.0202(3) Uani 1 1 d . . . H20 H 0.4967 0.2455 0.1418 0.024 Uiso 1 1 calc R . . C21 C 0.43714(8) 0.18548(6) 0.23211(15) 0.0175(3) Uani 1 1 d . . . H21 H 0.4569 0.1966 0.3113 0.021 Uiso 1 1 calc R . . C22 C 0.38323(8) 0.13991(6) 0.21807(14) 0.0143(3) Uani 1 1 d . . . C23 C 0.36068(8) 0.10903(6) 0.33371(14) 0.0171(3) Uani 1 1 d . . . H23 H 0.3213 0.0794 0.3084 0.021 Uiso 1 1 calc R . . C24 C 0.32685(9) 0.15147(7) 0.42501(16) 0.0226(3) Uani 1 1 d . . . H24A H 0.3660 0.1789 0.4561 0.034 Uiso 1 1 calc R . . H24B H 0.3093 0.1295 0.4927 0.034 Uiso 1 1 calc R . . H24C H 0.2841 0.1725 0.3833 0.034 Uiso 1 1 calc R . . C25 C 0.43084(9) 0.07731(7) 0.39949(16) 0.0243(3) Uani 1 1 d . . . H25A H 0.4511 0.0498 0.3435 0.036 Uiso 1 1 calc R . . H25B H 0.4154 0.0566 0.4703 0.036 Uiso 1 1 calc R . . H25C H 0.4699 0.1057 0.4259 0.036 Uiso 1 1 calc R . . C26 C 0.35357(8) 0.13479(6) -0.13963(14) 0.0161(3) Uani 1 1 d . . . H26 H 0.3273 0.0967 -0.1378 0.019 Uiso 1 1 calc R . . C27 C 0.42145(9) 0.12824(7) -0.21957(16) 0.0219(3) Uani 1 1 d . . . H27A H 0.4404 0.1665 -0.2391 0.033 Uiso 1 1 calc R . . H27B H 0.4044 0.1079 -0.2948 0.033 Uiso 1 1 calc R . . H27C H 0.4621 0.1062 -0.1749 0.033 Uiso 1 1 calc R . . C28 C 0.29651(9) 0.17945(7) -0.20264(16) 0.0230(3) Uani 1 1 d . . . H28A H 0.2518 0.1821 -0.1571 0.035 Uiso 1 1 calc R . . H28B H 0.2811 0.1668 -0.2858 0.035 Uiso 1 1 calc R . . H28C H 0.3209 0.2173 -0.2045 0.035 Uiso 1 1 calc R . . C29 C 0.17451(8) 0.13522(6) 0.09902(15) 0.0144(3) Uani 1 1 d . . . C30 C 0.11598(8) 0.13998(7) -0.01641(16) 0.0198(3) Uani 1 1 d . . . H30A H 0.0844 0.1743 -0.0096 0.030 Uiso 1 1 calc R . . H30B H 0.0838 0.1056 -0.0223 0.030 Uiso 1 1 calc R . . H30C H 0.1433 0.1430 -0.0892 0.030 Uiso 1 1 calc R . . C31 C 0.21720(8) 0.19428(6) 0.11138(15) 0.0184(3) Uani 1 1 d . . . H31A H 0.2459 0.2001 0.0408 0.028 Uiso 1 1 calc R . . H31B H 0.2521 0.1941 0.1854 0.028 Uiso 1 1 calc R . . H31C H 0.1804 0.2256 0.1157 0.028 Uiso 1 1 calc R . . C32 C 0.13032(9) 0.12921(7) 0.21543(16) 0.0203(3) Uani 1 1 d . . . H32A H 0.1665 0.1237 0.2869 0.030 Uiso 1 1 calc R . . H32B H 0.0963 0.0959 0.2063 0.030 Uiso 1 1 calc R . . H32C H 0.1007 0.1643 0.2256 0.030 Uiso 1 1 calc R . . C33 C 0.13006(8) -0.07627(6) 0.06691(14) 0.0137(3) Uani 1 1 d . . . C34 C 0.08357(8) -0.06501(7) 0.17941(15) 0.0178(3) Uani 1 1 d . . . H34A H 0.0397 -0.0909 0.1754 0.027 Uiso 1 1 calc R . . H34B H 0.0662 -0.0249 0.1783 0.027 Uiso 1 1 calc R . . H34C H 0.1159 -0.0723 0.2545 0.027 Uiso 1 1 calc R . . C35 C 0.14656(8) -0.14265(6) 0.06798(15) 0.0173(3) Uani 1 1 d . . . H35A H 0.0987 -0.1639 0.0650 0.026 Uiso 1 1 calc R . . H35B H 0.1781 -0.1528 0.1423 0.026 Uiso 1 1 calc R . . H35C H 0.1733 -0.1528 -0.0027 0.026 Uiso 1 1 calc R . . C36 C 0.07910(8) -0.06274(7) -0.05374(15) 0.0185(3) Uani 1 1 d . . . H36A H 0.1097 -0.0655 -0.1229 0.028 Uiso 1 1 calc R . . H36B H 0.0584 -0.0237 -0.0497 0.028 Uiso 1 1 calc R . . H36C H 0.0374 -0.0906 -0.0638 0.028 Uiso 1 1 calc R . . C37 C 0.25016(10) 0.01278(7) 0.53440(16) 0.0253(4) Uani 1 1 d . . . D37 D 0.2955 0.0077 0.4963 0.030 Uiso 1 1 calc R . . C38 C 0.25389(10) 0.02107(7) 0.66068(16) 0.0244(4) Uani 1 1 d . . . D38 D 0.3016 0.0215 0.7074 0.029 Uiso 1 1 calc R . . C39 C 0.18708(11) 0.02866(8) 0.71759(18) 0.0326(4) Uani 1 1 d . . . D39 D 0.1894 0.0343 0.8028 0.039 Uiso 1 1 calc R . . C40 C 0.11672(12) 0.02785(10) 0.6477(2) 0.0469(6) Uani 1 1 d . . . D40 D 0.0713 0.0328 0.6858 0.056 Uiso 1 1 calc R . . C41 C 0.11364(11) 0.01964(10) 0.5205(2) 0.0482(6) Uani 1 1 d . . . D41 D 0.0662 0.0193 0.4732 0.058 Uiso 1 1 calc R . . C42 C 0.18052(11) 0.01200(8) 0.46458(18) 0.0348(4) Uani 1 1 d . . . D42 D 0.1786 0.0063 0.3794 0.042 Uiso 1 1 calc R . . C43 C 1.05242(11) 0.18606(9) 0.6372(2) 0.0407(5) Uani 1 1 d . . . D43 D 1.1019 0.1785 0.6742 0.049 Uiso 1 1 calc R . . C44 C 1.00082(12) 0.21677(8) 0.7004(2) 0.0380(5) Uani 1 1 d . . . D44 D 1.0149 0.2301 0.7804 0.046 Uiso 1 1 calc R . . C45 C 0.92744(12) 0.22786(8) 0.6439(2) 0.0425(5) Uani 1 1 d . . . D45 D 0.8921 0.2489 0.6860 0.051 Uiso 1 1 calc R . . C46 C 0.90678(12) 0.20800(9) 0.5260(2) 0.0438(5) Uani 1 1 d . . . D46 D 0.8574 0.2154 0.4887 0.053 Uiso 1 1 calc R . . C47 C 0.95832(15) 0.17755(10) 0.4637(2) 0.0517(6) Uani 1 1 d . . . D47 D 0.9443 0.1643 0.3836 0.062 Uiso 1 1 calc R . . C48 C 1.03113(14) 0.16648(11) 0.5192(2) 0.0511(6) Uani 1 1 d . . . D48 D 1.0663 0.1455 0.4766 0.061 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 Ni1 0.00621(8) 0.01187(9) 0.01402(10) -0.00026(7) 0.00166(6) 0.00020(7) O1 0.0098(4) 0.0222(5) 0.0132(5) 0.0011(4) 0.0019(4) 0.0017(4) O2 0.0077(4) 0.0188(5) 0.0142(5) -0.0009(4) -0.0002(4) 0.0003(4) N1 0.0089(5) 0.0122(5) 0.0095(6) -0.0004(4) 0.0001(4) 0.0006(4) N2 0.0099(5) 0.0126(6) 0.0109(7) -0.0004(4) -0.0004(5) -0.0010(4) C1 0.0121(6) 0.0088(6) 0.0147(7) 0.0002(5) 0.0005(5) 0.0002(5) C2 0.0087(6) 0.0105(6) 0.0150(8) 0.0000(5) 0.0019(5) -0.0015(5) C3 0.0122(6) 0.0151(7) 0.0162(8) -0.0000(6) 0.0035(6) -0.0022(5) C4 0.0228(8) 0.0162(7) 0.0230(9) -0.0032(6) 0.0059(7) 0.0006(6) C5 0.0238(8) 0.0121(7) 0.0316(10) 0.0032(6) 0.0061(7) 0.0041(6) C6 0.0197(7) 0.0173(7) 0.0216(9) 0.0081(6) 0.0023(6) 0.0023(6) C7 0.0115(6) 0.0154(7) 0.0160(8) 0.0033(6) 0.0016(6) -0.0010(5) C8 0.0190(7) 0.0194(7) 0.0130(8) 0.0042(6) 0.0006(6) 0.0019(6) C9 0.0211(8) 0.0332(9) 0.0155(9) 0.0010(7) 0.0005(6) -0.0037(7) C10 0.0225(8) 0.0305(9) 0.0171(9) 0.0032(7) 0.0038(7) -0.0018(7) C11 0.0214(7) 0.0186(7) 0.0132(8) -0.0025(6) 0.0020(6) 0.0021(6) C12 0.0260(8) 0.0223(8) 0.0176(9) -0.0033(6) 0.0056(7) -0.0020(6) C13 0.0230(8) 0.0393(10) 0.0177(9) -0.0058(7) 0.0019(7) -0.0008(7) C14 0.0093(6) 0.0152(6) 0.0088(7) 0.0000(5) -0.0003(5) -0.0008(5) C15 0.0062(6) 0.0175(7) 0.0153(8) -0.0009(6) 0.0010(5) 0.0005(5) C16 0.0107(6) 0.0157(7) 0.0081(7) -0.0012(5) -0.0006(5) 0.0026(5) C17 0.0087(6) 0.0096(6) 0.0176(8) -0.0021(5) 0.0013(5) 0.0012(5) C18 0.0121(6) 0.0124(6) 0.0175(8) 0.0005(6) 0.0025(6) 0.0026(5) C19 0.0171(7) 0.0141(7) 0.0247(9) 0.0023(6) 0.0054(6) -0.0011(5) C20 0.0138(7) 0.0146(7) 0.0323(10) -0.0048(6) 0.0018(6) -0.0043(5) C21 0.0140(7) 0.0181(7) 0.0198(9) -0.0070(6) -0.0019(6) -0.0004(5) C22 0.0117(6) 0.0139(6) 0.0171(8) -0.0016(6) 0.0008(6) 0.0009(5) C23 0.0186(7) 0.0194(7) 0.0129(8) -0.0031(6) -0.0010(6) -0.0028(6) C24 0.0236(8) 0.0262(8) 0.0183(9) -0.0034(7) 0.0029(7) -0.0008(6) C25 0.0283(8) 0.0266(8) 0.0170(9) -0.0019(7) -0.0027(7) 0.0043(7) C26 0.0194(7) 0.0154(7) 0.0140(8) 0.0015(6) 0.0036(6) -0.0018(5) C27 0.0269(8) 0.0196(7) 0.0202(9) 0.0030(6) 0.0076(7) 0.0028(6) C28 0.0223(8) 0.0264(8) 0.0201(9) 0.0030(7) 0.0007(6) 0.0029(6) C29 0.0102(6) 0.0151(7) 0.0179(8) -0.0021(6) 0.0010(6) 0.0032(5) C30 0.0137(7) 0.0196(7) 0.0253(9) 0.0014(6) -0.0023(6) 0.0032(6) C31 0.0159(7) 0.0145(7) 0.0247(9) -0.0031(6) 0.0018(6) 0.0043(5) C32 0.0184(7) 0.0211(7) 0.0225(9) -0.0040(6) 0.0076(6) 0.0031(6) C33 0.0094(6) 0.0164(7) 0.0154(8) -0.0002(6) 0.0013(6) -0.0020(5) C34 0.0126(7) 0.0213(7) 0.0201(9) -0.0003(6) 0.0047(6) -0.0034(5) C35 0.0134(7) 0.0165(7) 0.0223(9) -0.0012(6) 0.0029(6) -0.0055(5) C36 0.0120(7) 0.0230(7) 0.0197(9) -0.0005(6) -0.0020(6) -0.0042(6) C37 0.0296(8) 0.0232(8) 0.0235(9) -0.0015(7) 0.0052(7) -0.0016(6) C38 0.0304(8) 0.0189(8) 0.0232(10) 0.0008(6) -0.0026(7) -0.0032(6) C39 0.0487(11) 0.0294(9) 0.0210(10) 0.0025(7) 0.0098(8) 0.0034(8) C40 0.0327(10) 0.0563(13) 0.0550(15) 0.0121(11) 0.0215(10) 0.0090(9) C41 0.0285(10) 0.0655(14) 0.0484(15) 0.0100(11) -0.0094(9) -0.0031(9) C42 0.0425(10) 0.0393(10) 0.0212(10) -0.0005(8) -0.0040(8) -0.0062(8) C43 0.0294(9) 0.0467(11) 0.0456(14) 0.0187(10) 0.0010(9) -0.0050(8) C44 0.0534(12) 0.0293(9) 0.0306(11) 0.0055(8) 0.0007(9) -0.0119(9) C45 0.0480(12) 0.0284(9) 0.0532(15) 0.0125(9) 0.0165(11) 0.0044(8) C46 0.0344(10) 0.0394(11) 0.0555(16) 0.0181(10) -0.0078(10) -0.0076(8) C47 0.0685(15) 0.0489(13) 0.0357(14) 0.0021(10) -0.0069(11) -0.0084(11) C48 0.0557(13) 0.0593(14) 0.0410(14) 0.0074(11) 0.0183(11) 0.0111(11) _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 Ni1 N1 1.9008(11) . ? Ni1 N2 1.9111(11) . ? Ni1 O2 1.9927(10) 3_655 ? Ni1 O1 2.0073(10) . ? O1 C1 1.2553(16) . ? O2 C1 1.2534(16) . ? O2 Ni1 1.9927(10) 3_655 ? N1 C14 1.3363(17) . ? N1 C2 1.4378(17) . ? N2 C16 1.3321(17) . ? N2 C17 1.4422(17) . ? C1 C1 1.527(3) 3_655 ? C2 C7 1.407(2) . ? C2 C3 1.411(2) . ? C3 C4 1.390(2) . ? C3 C11 1.518(2) . ? C4 C5 1.379(2) . ? C4 H4 0.9300 . ? C5 C6 1.379(2) . ? C5 H5 0.9300 . ? C6 C7 1.394(2) . ? C6 H6 0.9300 . ? C7 C8 1.522(2) . ? C8 C9 1.531(2) . ? C8 C10 1.532(2) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C13 1.533(2) . ? C11 C12 1.534(2) . ? C11 H11 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.4036(19) . ? C14 C33 1.5613(18) . ? C15 C16 1.4043(19) . ? C15 H15 0.9300 . ? C16 C29 1.5626(18) . ? C17 C22 1.405(2) . ? C17 C18 1.411(2) . ? C18 C19 1.398(2) . ? C18 C26 1.517(2) . ? C19 C20 1.376(2) . ? C19 H19 0.9300 . ? C20 C21 1.384(2) . ? C20 H20 0.9300 . ? C21 C22 1.3944(19) . ? C21 H21 0.9300 . ? C22 C23 1.519(2) . ? C23 C25 1.534(2) . ? C23 C24 1.536(2) . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.534(2) . ? C26 C28 1.534(2) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.5321(19) . ? C29 C30 1.542(2) . ? C29 C32 1.543(2) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C35 1.5340(19) . ? C33 C36 1.542(2) . ? C33 C34 1.545(2) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C42 1.367(3) . ? C37 C38 1.378(2) . ? C37 D37 0.9300 . ? C38 C39 1.374(2) . ? C38 D38 0.9300 . ? C39 C40 1.378(3) . ? C39 D39 0.9300 . ? C40 C41 1.389(3) . ? C40 D40 0.9300 . ? C41 C42 1.370(3) . ? C41 D41 0.9300 . ? C42 D42 0.9300 . ? C43 C44 1.368(3) . ? C43 C48 1.373(3) . ? C43 D43 0.9300 . ? C44 C45 1.386(3) . ? C44 D44 0.9300 . ? C45 C46 1.371(3) . ? C45 D45 0.9300 . ? C46 C47 1.359(3) . ? C46 D46 0.9300 . ? C47 C48 1.373(3) . ? C47 D47 0.9300 . ? C48 D48 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N2 97.71(5) . . ? N1 Ni1 O2 116.39(4) . 3_655 ? N2 Ni1 O2 116.82(5) . 3_655 ? N1 Ni1 O1 127.97(5) . . ? N2 Ni1 O1 116.22(5) . . ? O2 Ni1 O1 83.20(4) 3_655 . ? C1 O1 Ni1 111.33(9) . . ? C1 O2 Ni1 111.96(9) . 3_655 ? C14 N1 C2 126.28(11) . . ? C14 N1 Ni1 124.53(9) . . ? C2 N1 Ni1 109.01(8) . . ? C16 N2 C17 126.49(11) . . ? C16 N2 Ni1 124.43(9) . . ? C17 N2 Ni1 109.00(8) . . ? O2 C1 O1 126.52(13) . . ? O2 C1 C1 116.66(14) . 3_655 ? O1 C1 C1 116.81(14) . 3_655 ? C7 C2 C3 120.90(12) . . ? C7 C2 N1 118.65(12) . . ? C3 C2 N1 120.20(13) . . ? C4 C3 C2 117.96(14) . . ? C4 C3 C11 118.76(13) . . ? C2 C3 C11 123.28(12) . . ? C5 C4 C3 121.81(15) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.47(14) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C7 121.53(15) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C6 C7 C2 118.14(14) . . ? C6 C7 C8 118.61(14) . . ? C2 C7 C8 123.25(12) . . ? C7 C8 C9 110.55(12) . . ? C7 C8 C10 112.10(12) . . ? C9 C8 C10 109.67(13) . . ? C7 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? C10 C8 H8 108.1 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 C13 112.64(13) . . ? C3 C11 C12 111.29(12) . . ? C13 C11 C12 108.36(13) . . ? C3 C11 H11 108.1 . . ? C13 C11 H11 108.1 . . ? C12 C11 H11 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 C15 120.40(12) . . ? N1 C14 C33 125.77(12) . . ? C15 C14 C33 113.76(11) . . ? C14 C15 C16 132.19(12) . . ? C14 C15 H15 113.9 . . ? C16 C15 H15 113.9 . . ? N2 C16 C15 120.37(12) . . ? N2 C16 C29 126.10(12) . . ? C15 C16 C29 113.53(11) . . ? C22 C17 C18 121.40(12) . . ? C22 C17 N2 119.29(12) . . ? C18 C17 N2 118.96(13) . . ? C19 C18 C17 117.60(14) . . ? C19 C18 C26 118.75(13) . . ? C17 C18 C26 123.65(12) . . ? C20 C19 C18 121.71(14) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 119.72(13) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 121.34(15) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C21 C22 C17 118.07(13) . . ? C21 C22 C23 118.29(14) . . ? C17 C22 C23 123.64(12) . . ? C22 C23 C25 110.26(12) . . ? C22 C23 C24 112.66(12) . . ? C25 C23 C24 109.23(13) . . ? C22 C23 H23 108.2 . . ? C25 C23 H23 108.2 . . ? C24 C23 H23 108.2 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C26 C27 111.94(12) . . ? C18 C26 C28 112.46(12) . . ? C27 C26 C28 108.14(13) . . ? C18 C26 H26 108.0 . . ? C27 C26 H26 108.0 . . ? C28 C26 H26 108.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 C30 106.70(12) . . ? C31 C29 C32 106.21(12) . . ? C30 C29 C32 109.26(12) . . ? C31 C29 C16 117.83(11) . . ? C30 C29 C16 107.98(12) . . ? C32 C29 C16 108.64(12) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C35 C33 C36 107.12(12) . . ? C35 C33 C34 105.51(11) . . ? C36 C33 C34 109.64(12) . . ? C35 C33 C14 118.10(11) . . ? C36 C33 C14 106.35(11) . . ? C34 C33 C14 109.94(12) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C42 C37 C38 120.71(16) . . ? C42 C37 D37 119.6 . . ? C38 C37 D37 119.6 . . ? C39 C38 C37 119.93(17) . . ? C39 C38 D38 120.0 . . ? C37 C38 D38 120.0 . . ? C38 C39 C40 119.63(18) . . ? C38 C39 D39 120.2 . . ? C40 C39 D39 120.2 . . ? C39 C40 C41 119.96(18) . . ? C39 C40 D40 120.0 . . ? C41 C40 D40 120.0 . . ? C42 C41 C40 119.99(19) . . ? C42 C41 D41 120.0 . . ? C40 C41 D41 120.0 . . ? C37 C42 C41 119.78(18) . . ? C37 C42 D42 120.1 . . ? C41 C42 D42 120.1 . . ? C44 C43 C48 119.9(2) . . ? C44 C43 D43 120.0 . . ? C48 C43 D43 120.0 . . ? C43 C44 C45 119.3(2) . . ? C43 C44 D44 120.3 . . ? C45 C44 D44 120.3 . . ? C46 C45 C44 120.2(2) . . ? C46 C45 D45 119.9 . . ? C44 C45 D45 119.9 . . ? C47 C46 C45 120.2(2) . . ? C47 C46 D46 119.9 . . ? C45 C46 D46 119.9 . . ? C46 C47 C48 119.8(2) . . ? C46 C47 D47 120.1 . . ? C48 C47 D47 120.1 . . ? C43 C48 C47 120.5(2) . . ? C43 C48 D48 119.7 . . ? C47 C48 D48 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 O1 C1 119.89(9) . . . . ? N2 Ni1 O1 C1 -115.06(9) . . . . ? O2 Ni1 O1 C1 1.54(9) 3_655 . . . ? N2 Ni1 N1 C14 4.87(12) . . . . ? O2 Ni1 N1 C14 -120.26(11) 3_655 . . . ? O1 Ni1 N1 C14 137.05(11) . . . . ? N2 Ni1 N1 C2 -170.44(9) . . . . ? O2 Ni1 N1 C2 64.42(10) 3_655 . . . ? O1 Ni1 N1 C2 -38.27(11) . . . . ? N1 Ni1 N2 C16 -5.43(12) . . . . ? O2 Ni1 N2 C16 119.41(11) 3_655 . . . ? O1 Ni1 N2 C16 -144.79(11) . . . . ? N1 Ni1 N2 C17 171.44(9) . . . . ? O2 Ni1 N2 C17 -63.73(10) 3_655 . . . ? O1 Ni1 N2 C17 32.08(11) . . . . ? Ni1 O2 C1 O1 178.64(11) 3_655 . . . ? Ni1 O2 C1 C1 -0.96(18) 3_655 . . 3_655 ? Ni1 O1 C1 O2 178.95(11) . . . . ? Ni1 O1 C1 C1 -1.45(18) . . . 3_655 ? C14 N1 C2 C7 -86.89(17) . . . . ? Ni1 N1 C2 C7 88.33(12) . . . . ? C14 N1 C2 C3 98.88(16) . . . . ? Ni1 N1 C2 C3 -85.91(13) . . . . ? C7 C2 C3 C4 4.9(2) . . . . ? N1 C2 C3 C4 179.05(12) . . . . ? C7 C2 C3 C11 -175.49(12) . . . . ? N1 C2 C3 C11 -1.38(19) . . . . ? C2 C3 C4 C5 -2.3(2) . . . . ? C11 C3 C4 C5 178.15(13) . . . . ? C3 C4 C5 C6 -1.1(2) . . . . ? C4 C5 C6 C7 2.0(2) . . . . ? C5 C6 C7 C2 0.7(2) . . . . ? C5 C6 C7 C8 -179.87(13) . . . . ? C3 C2 C7 C6 -4.17(19) . . . . ? N1 C2 C7 C6 -178.37(12) . . . . ? C3 C2 C7 C8 176.39(12) . . . . ? N1 C2 C7 C8 2.19(19) . . . . ? C6 C7 C8 C9 63.20(17) . . . . ? C2 C7 C8 C9 -117.36(15) . . . . ? C6 C7 C8 C10 -59.50(17) . . . . ? C2 C7 C8 C10 119.94(15) . . . . ? C4 C3 C11 C13 68.16(17) . . . . ? C2 C3 C11 C13 -111.41(15) . . . . ? C4 C3 C11 C12 -53.77(17) . . . . ? C2 C3 C11 C12 126.67(14) . . . . ? C2 N1 C14 C15 173.29(14) . . . . ? Ni1 N1 C14 C15 -1.2(2) . . . . ? C2 N1 C14 C33 -9.9(2) . . . . ? Ni1 N1 C14 C33 175.61(11) . . . . ? N1 C14 C15 C16 -4.4(3) . . . . ? C33 C14 C15 C16 178.45(15) . . . . ? C17 N2 C16 C15 -174.03(14) . . . . ? Ni1 N2 C16 C15 2.3(2) . . . . ? C17 N2 C16 C29 7.1(2) . . . . ? Ni1 N2 C16 C29 -176.61(11) . . . . ? C14 C15 C16 N2 3.8(3) . . . . ? C14 C15 C16 C29 -177.21(16) . . . . ? C16 N2 C17 C22 85.08(18) . . . . ? Ni1 N2 C17 C22 -91.70(12) . . . . ? C16 N2 C17 C18 -101.66(16) . . . . ? Ni1 N2 C17 C18 81.55(13) . . . . ? C22 C17 C18 C19 -4.17(19) . . . . ? N2 C17 C18 C19 -177.27(12) . . . . ? C22 C17 C18 C26 176.30(12) . . . . ? N2 C17 C18 C26 3.20(19) . . . . ? C17 C18 C19 C20 1.0(2) . . . . ? C26 C18 C19 C20 -179.47(13) . . . . ? C18 C19 C20 C21 2.0(2) . . . . ? C19 C20 C21 C22 -1.9(2) . . . . ? C20 C21 C22 C17 -1.2(2) . . . . ? C20 C21 C22 C23 178.27(13) . . . . ? C18 C17 C22 C21 4.29(19) . . . . ? N2 C17 C22 C21 177.37(12) . . . . ? C18 C17 C22 C23 -175.16(13) . . . . ? N2 C17 C22 C23 -2.08(19) . . . . ? C21 C22 C23 C25 -63.90(17) . . . . ? C17 C22 C23 C25 115.55(15) . . . . ? C21 C22 C23 C24 58.42(17) . . . . ? C17 C22 C23 C24 -122.13(15) . . . . ? C19 C18 C26 C27 46.38(17) . . . . ? C17 C18 C26 C27 -134.09(13) . . . . ? C19 C18 C26 C28 -75.61(16) . . . . ? C17 C18 C26 C28 103.92(15) . . . . ? N2 C16 C29 C31 -2.5(2) . . . . ? C15 C16 C29 C31 178.57(13) . . . . ? N2 C16 C29 C30 118.38(15) . . . . ? C15 C16 C29 C30 -60.57(16) . . . . ? N2 C16 C29 C32 -123.23(15) . . . . ? C15 C16 C29 C32 57.81(17) . . . . ? N1 C14 C33 C35 7.3(2) . . . . ? C15 C14 C33 C35 -175.70(13) . . . . ? N1 C14 C33 C36 -113.01(15) . . . . ? C15 C14 C33 C36 64.00(16) . . . . ? N1 C14 C33 C34 128.37(15) . . . . ? C15 C14 C33 C34 -54.62(17) . . . . ? C42 C37 C38 C39 0.0(2) . . . . ? C37 C38 C39 C40 0.1(3) . . . . ? C38 C39 C40 C41 -0.3(3) . . . . ? C39 C40 C41 C42 0.4(3) . . . . ? C38 C37 C42 C41 0.1(3) . . . . ? C40 C41 C42 C37 -0.3(3) . . . . ? C48 C43 C44 C45 -0.2(3) . . . . ? C43 C44 C45 C46 0.3(3) . . . . ? C44 C45 C46 C47 -0.3(3) . . . . ? C45 C46 C47 C48 0.3(3) . . . . ? C44 C43 C48 C47 0.1(3) . . . . ? C46 C47 C48 C43 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.276 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 950231'