# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_dma48_0m _database_code_depnum_ccdc_archive 'CCDC 843769' #TrackingRef '7133_web_deposit_cif_file_0_DavidMcMorran_1315712607.dma48_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 N10 Ni, 2(C2 H3 N)' _chemical_formula_sum 'C32 H34 N12 Ni' _chemical_formula_weight 645.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.985(6) _cell_length_b 10.573(4) _cell_length_c 18.103(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.717(19) _cell_angle_gamma 90.00 _cell_volume 3127.1(19) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 3137 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 23.48 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6913 _exptl_absorpt_correction_T_max 0.9245 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 'Bruker Kappa ApexII area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 20854 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 24.94 _reflns_number_total 2715 _reflns_number_gt 2162 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0337P)^2^+4.6146P] 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 2715 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.7500 0.2500 0.5000 0.01379(14) Uani 1 2 d S . . N1 N 0.74274(12) 0.2038(2) 0.39856(12) 0.0179(5) Uani 1 1 d . . . H1 H 0.7828(15) 0.173(2) 0.3962(14) 0.015(7) Uiso 1 1 d . . . C1 C 0.67767(14) 0.1978(2) 0.32890(14) 0.0161(5) Uani 1 1 d . . . N2 N 0.89875(11) 0.27078(18) 0.68360(11) 0.0160(4) Uani 1 1 d . . . C2 C 0.91384(13) 0.2238(2) 0.62211(13) 0.0153(5) Uani 1 1 d . . . N3 N 0.85846(12) 0.20127(19) 0.54774(12) 0.0163(4) Uani 1 1 d . . . H3 H 0.8779(14) 0.159(2) 0.5202(14) 0.012(6) Uiso 1 1 d . . . N4 N 0.68157(12) 0.1523(2) 0.25918(12) 0.0185(5) Uani 1 1 d . . . H4 H 0.6374(15) 0.126(2) 0.2244(14) 0.012(6) Uiso 1 1 d . . . C3 C 0.74895(14) 0.1419(2) 0.24004(14) 0.0172(5) Uani 1 1 d . . . C4 C 0.74325(14) 0.0546(2) 0.18010(14) 0.0189(5) Uani 1 1 d . . . H4A H 0.6962 0.0060 0.1552 0.023 Uiso 1 1 calc R . . C5 C 0.80743(15) 0.0404(2) 0.15775(14) 0.0225(6) Uani 1 1 d . . . H5A H 0.8032 -0.0176 0.1175 0.027 Uiso 1 1 calc R . . C6 C 0.87772(15) 0.1113(2) 0.19450(14) 0.0245(6) Uani 1 1 d . . . H6A H 0.9215 0.0993 0.1807 0.029 Uiso 1 1 calc R . . C7 C 0.88242(15) 0.2003(3) 0.25200(15) 0.0241(6) Uani 1 1 d . . . H7A H 0.9292 0.2497 0.2759 0.029 Uiso 1 1 calc R . . C8 C 0.81833(14) 0.2171(2) 0.27462(14) 0.0202(6) Uani 1 1 d . . . H8A H 0.8218 0.2785 0.3128 0.024 Uiso 1 1 calc R . . N5 N 0.99457(12) 0.1958(2) 0.64600(13) 0.0174(5) Uani 1 1 d . . . H5 H 1.0206(14) 0.212(2) 0.6918(15) 0.008(6) Uiso 1 1 d . . . C11 C 1.03753(13) 0.1664(2) 0.59892(13) 0.0153(5) Uani 1 1 d . . . C12 C 1.01154(14) 0.1971(2) 0.51713(14) 0.0199(5) Uani 1 1 d . . . H12A H 0.9617 0.2378 0.4894 0.024 Uiso 1 1 calc R . . C13 C 1.06013(15) 0.1668(2) 0.47731(15) 0.0229(6) Uani 1 1 d . . . H13A H 1.0412 0.1832 0.4220 0.027 Uiso 1 1 calc R . . C14 C 1.13595(15) 0.1128(2) 0.51831(15) 0.0223(6) Uani 1 1 d . . . H14A H 1.1686 0.0941 0.4912 0.027 Uiso 1 1 calc R . . C15 C 1.16311(15) 0.0864(2) 0.60035(15) 0.0210(6) Uani 1 1 d . . . H15A H 1.2151 0.0527 0.6290 0.025 Uiso 1 1 calc R . . C16 C 1.11359(14) 0.1099(2) 0.63969(14) 0.0177(5) Uani 1 1 d . . . H16A H 1.1312 0.0877 0.6941 0.021 Uiso 1 1 calc R . . N20 N 0.53354(16) -0.0104(3) 0.12887(16) 0.0485(7) Uani 1 1 d . . . C20 C 0.46488(19) -0.0268(3) 0.09987(19) 0.0408(8) Uani 1 1 d . . . C21 C 0.37667(18) -0.0487(3) 0.0636(2) 0.0610(11) Uani 1 1 d . . . H21A H 0.3622 -0.0976 0.1003 0.092 Uiso 1 1 calc R . . H21B H 0.3613 -0.0938 0.0134 0.092 Uiso 1 1 calc R . . H21C H 0.3486 0.0310 0.0534 0.092 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 0.0094(2) 0.0220(2) 0.0093(2) -0.00077(17) 0.00326(17) 0.00098(18) N1 0.0102(11) 0.0289(12) 0.0148(11) -0.0021(8) 0.0055(9) 0.0031(9) C1 0.0175(13) 0.0184(12) 0.0141(12) -0.0011(10) 0.0082(10) -0.0003(10) N2 0.0099(10) 0.0266(12) 0.0112(10) 0.0011(8) 0.0041(8) 0.0018(8) C2 0.0133(12) 0.0201(13) 0.0121(12) 0.0016(9) 0.0050(10) 0.0001(9) N3 0.0136(10) 0.0252(11) 0.0118(10) -0.0021(9) 0.0069(9) 0.0030(9) N4 0.0099(11) 0.0317(13) 0.0114(11) -0.0053(9) 0.0019(9) 0.0002(9) C3 0.0162(12) 0.0237(13) 0.0121(12) 0.0032(10) 0.0063(10) 0.0042(10) C4 0.0215(13) 0.0211(13) 0.0153(12) 0.0012(10) 0.0087(11) 0.0013(10) C5 0.0288(15) 0.0269(14) 0.0162(13) 0.0014(10) 0.0138(11) 0.0054(11) C6 0.0233(14) 0.0371(15) 0.0189(13) 0.0034(11) 0.0146(11) 0.0049(12) C7 0.0165(13) 0.0347(15) 0.0196(14) 0.0036(11) 0.0059(11) -0.0030(11) C8 0.0194(13) 0.0289(14) 0.0132(12) -0.0011(10) 0.0076(10) 0.0001(10) N5 0.0118(11) 0.0311(12) 0.0080(11) -0.0013(9) 0.0027(9) 0.0021(9) C11 0.0131(12) 0.0186(12) 0.0154(12) -0.0010(10) 0.0070(10) -0.0016(10) C12 0.0144(12) 0.0277(13) 0.0169(13) 0.0013(10) 0.0058(10) 0.0013(10) C13 0.0259(14) 0.0310(15) 0.0151(13) 0.0006(11) 0.0119(11) -0.0006(12) C14 0.0229(14) 0.0254(13) 0.0248(14) -0.0033(11) 0.0161(12) -0.0013(11) C15 0.0173(13) 0.0239(14) 0.0233(14) 0.0016(11) 0.0100(11) 0.0040(10) C16 0.0179(13) 0.0204(12) 0.0149(12) 0.0017(10) 0.0069(10) 0.0017(10) N20 0.0343(17) 0.0422(16) 0.0538(18) -0.0063(13) 0.0032(14) -0.0052(13) C20 0.0366(19) 0.0263(16) 0.0465(19) -0.0055(14) 0.0044(16) 0.0031(14) C21 0.0293(18) 0.041(2) 0.088(3) -0.0169(19) 0.0000(18) 0.0079(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N3 1.846(2) 7_656 ? Ni1 N3 1.846(2) . ? Ni1 N1 1.851(2) . ? Ni1 N1 1.851(2) 7_656 ? N1 C1 1.315(3) . ? N1 H1 0.81(3) . ? C1 N2 1.338(3) 7_656 ? C1 N4 1.380(3) . ? N2 C1 1.338(3) 7_656 ? N2 C2 1.346(3) . ? C2 N3 1.319(3) . ? C2 N5 1.363(3) . ? N3 H3 0.85(2) . ? N4 C3 1.397(3) . ? N4 H4 0.83(2) . ? C3 C8 1.389(3) . ? C3 C4 1.395(3) . ? C4 C5 1.382(3) . ? C4 H4A 0.9300 . ? C5 C6 1.378(3) . ? C5 H5A 0.9300 . ? C6 C7 1.379(4) . ? C6 H6A 0.9300 . ? C7 C8 1.386(3) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? N5 C11 1.404(3) . ? N5 H5 0.78(2) . ? C11 C16 1.389(3) . ? C11 C12 1.392(3) . ? C12 C13 1.383(3) . ? C12 H12A 0.9300 . ? C13 C14 1.375(3) . ? C13 H13A 0.9300 . ? C14 C15 1.384(3) . ? C14 H14A 0.9300 . ? C15 C16 1.376(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? N20 C20 1.135(4) . ? C20 C21 1.460(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 N3 Ni1 N3 180.0 7_656 . ? N3 Ni1 N1 89.24(9) 7_656 . ? N3 Ni1 N1 90.76(9) . . ? N3 Ni1 N1 90.76(9) 7_656 7_656 ? N3 Ni1 N1 89.24(9) . 7_656 ? N1 Ni1 N1 180.000(1) . 7_656 ? C1 N1 Ni1 129.01(17) . . ? C1 N1 H1 112.7(17) . . ? Ni1 N1 H1 117.6(17) . . ? N1 C1 N2 126.1(2) . 7_656 ? N1 C1 N4 121.9(2) . . ? N2 C1 N4 111.9(2) 7_656 . ? C1 N2 C2 119.99(19) 7_656 . ? N3 C2 N2 125.7(2) . . ? N3 C2 N5 122.3(2) . . ? N2 C2 N5 112.0(2) . . ? C2 N3 Ni1 128.79(17) . . ? C2 N3 H3 112.0(16) . . ? Ni1 N3 H3 119.2(16) . . ? C1 N4 C3 129.5(2) . . ? C1 N4 H4 114.4(16) . . ? C3 N4 H4 116.1(16) . . ? C8 C3 C4 119.3(2) . . ? C8 C3 N4 123.5(2) . . ? C4 C3 N4 117.1(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6A 120.3 . . ? C7 C6 H6A 120.3 . . ? C6 C7 C8 120.9(2) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C7 C8 C3 119.6(2) . . ? C7 C8 H8A 120.2 . . ? C3 C8 H8A 120.2 . . ? C2 N5 C11 129.7(2) . . ? C2 N5 H5 112.1(17) . . ? C11 N5 H5 117.1(17) . . ? C16 C11 C12 118.9(2) . . ? C16 C11 N5 116.3(2) . . ? C12 C11 N5 124.7(2) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12A 120.1 . . ? C11 C12 H12A 120.1 . . ? C14 C13 C12 121.0(2) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C15 C16 C11 120.6(2) . . ? C15 C16 H16A 119.7 . . ? C11 C16 H16A 119.7 . . ? N20 C20 C21 179.2(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 N3 Ni1 N1 C1 -8.0(2) 7_656 . . . ? N3 Ni1 N1 C1 172.0(2) . . . . ? N1 Ni1 N1 C1 -8(100) 7_656 . . . ? Ni1 N1 C1 N2 2.6(4) . . . 7_656 ? Ni1 N1 C1 N4 -175.10(17) . . . . ? C1 N2 C2 N3 -1.9(4) 7_656 . . . ? C1 N2 C2 N5 -179.3(2) 7_656 . . . ? N2 C2 N3 Ni1 11.5(4) . . . . ? N5 C2 N3 Ni1 -171.38(17) . . . . ? N3 Ni1 N3 C2 88(100) 7_656 . . . ? N1 Ni1 N3 C2 167.8(2) . . . . ? N1 Ni1 N3 C2 -12.2(2) 7_656 . . . ? N1 C1 N4 C3 -21.2(4) . . . . ? N2 C1 N4 C3 160.8(2) 7_656 . . . ? C1 N4 C3 C8 -25.1(4) . . . . ? C1 N4 C3 C4 158.0(2) . . . . ? C8 C3 C4 C5 2.3(3) . . . . ? N4 C3 C4 C5 179.4(2) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 -2.3(4) . . . . ? C5 C6 C7 C8 1.5(4) . . . . ? C6 C7 C8 C3 1.1(4) . . . . ? C4 C3 C8 C7 -3.1(3) . . . . ? N4 C3 C8 C7 -180.0(2) . . . . ? N3 C2 N5 C11 14.7(4) . . . . ? N2 C2 N5 C11 -167.8(2) . . . . ? C2 N5 C11 C16 -163.5(2) . . . . ? C2 N5 C11 C12 20.8(4) . . . . ? C16 C11 C12 C13 2.4(3) . . . . ? N5 C11 C12 C13 178.0(2) . . . . ? C11 C12 C13 C14 -3.5(4) . . . . ? C12 C13 C14 C15 1.2(4) . . . . ? C13 C14 C15 C16 2.3(4) . . . . ? C14 C15 C16 C11 -3.4(4) . . . . ? C12 C11 C16 C15 1.0(3) . . . . ? N5 C11 C16 C15 -174.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4 N20 0.83(2) 2.42(2) 3.219(3) 162(2) . N5 H5 N2 0.78(2) 2.20(2) 2.979(3) 174(2) 2_756 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.361 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.062 data_dma59b _database_code_depnum_ccdc_archive 'CCDC 843770' #TrackingRef '7134_web_deposit_cif_file_1_DavidMcMorran_1315712607.dma59b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H46 N10 Ni O8, 2(B F4), C3 O' _chemical_formula_sum 'C39 H46 B2 F8 N10 Ni O9' _chemical_formula_weight 1031.19 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 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' _cell_length_a 7.9360(9) _cell_length_b 8.5760(10) _cell_length_c 17.863(2) _cell_angle_alpha 93.507(4) _cell_angle_beta 90.073(4) _cell_angle_gamma 111.697(4) _cell_volume 1127.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 5247 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 24.54 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.529 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 18212 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 24.79 _reflns_number_total 3771 _reflns_number_gt 3018 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0956P)^2^+2.5037P] 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 3771 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.0000 0.0000 0.5000 0.0250(3) Uani 1 2 d S . . N1 N -0.0976(4) 0.0440(4) 0.58958(18) 0.0271(8) Uani 1 1 d . . . H1A H -0.2141 0.0021 0.5905 0.032 Uiso 1 1 calc R . . C1 C -0.0191(5) 0.1272(5) 0.6505(2) 0.0215(8) Uani 1 1 d . . . N2 N 0.1648(4) 0.1861(5) 0.6596(2) 0.0263(8) Uani 1 1 d . . . H2 H 0.203(7) 0.226(7) 0.697(3) 0.040(16) Uiso 1 1 d . . . C2 C 0.2847(5) 0.1636(5) 0.6096(2) 0.0243(9) Uani 1 1 d . . . N3 N 0.2318(5) 0.0909(5) 0.5435(2) 0.0300(8) Uani 1 1 d . . . H3 H 0.321(7) 0.083(6) 0.518(3) 0.038(13) Uiso 1 1 d . . . N4 N -0.1120(5) 0.1616(5) 0.70878(19) 0.0256(8) Uani 1 1 d . . . H4 H -0.222(7) 0.109(6) 0.706(3) 0.035(13) Uiso 1 1 d . . . C3 C -0.0386(5) 0.2314(5) 0.7816(2) 0.0248(9) Uani 1 1 d . . . C4 C 0.0982(5) 0.3908(5) 0.7906(2) 0.0262(9) Uani 1 1 d . . . H4A H 0.1432 0.4537 0.7495 0.031 Uiso 1 1 calc R . . C5 C 0.1648(5) 0.4525(5) 0.8625(2) 0.0294(10) Uani 1 1 d . . . C6 C 0.0929(5) 0.3619(5) 0.9247(2) 0.0278(9) Uani 1 1 d . . . H6A H 0.1382 0.4055 0.9727 0.033 Uiso 1 1 calc R . . C7 C -0.0455(5) 0.2074(5) 0.9145(2) 0.0272(9) Uani 1 1 d . . . C8 C -0.1112(5) 0.1396(5) 0.8426(2) 0.0248(9) Uani 1 1 d . . . H8A H -0.2028 0.0339 0.8358 0.030 Uiso 1 1 calc R . . O1 O 0.2997(4) 0.6048(4) 0.87934(18) 0.0361(7) Uani 1 1 d . . . C9 C 0.3773(6) 0.7075(6) 0.8187(3) 0.0405(11) Uani 1 1 d . . . H9A H 0.4705 0.8102 0.8380 0.061 Uiso 1 1 calc R . . H9B H 0.2847 0.7329 0.7934 0.061 Uiso 1 1 calc R . . H9C H 0.4287 0.6484 0.7841 0.061 Uiso 1 1 calc R . . O2 O -0.1264(4) 0.1104(4) 0.97138(16) 0.0331(7) Uani 1 1 d . . . C10 C -0.0539(6) 0.1695(6) 1.0460(2) 0.0371(11) Uani 1 1 d . . . H10A H -0.1202 0.0893 1.0808 0.056 Uiso 1 1 calc R . . H10B H -0.0648 0.2757 1.0589 0.056 Uiso 1 1 calc R . . H10C H 0.0716 0.1830 1.0482 0.056 Uiso 1 1 calc R . . N5 N 0.4615(5) 0.2263(5) 0.6333(2) 0.0301(8) Uani 1 1 d . . . H5 H 0.528(7) 0.235(6) 0.604(3) 0.032(15) Uiso 1 1 d . . . C11 C 0.5236(5) 0.2892(5) 0.7079(2) 0.0271(9) Uani 1 1 d . . . C12 C 0.6528(5) 0.4518(5) 0.7181(2) 0.0275(9) Uani 1 1 d . . . H12A H 0.6975 0.5166 0.6775 0.033 Uiso 1 1 calc R . . C13 C 0.7119(5) 0.5132(5) 0.7904(2) 0.0285(9) Uani 1 1 d . . . C14 C 0.6422(5) 0.4200(5) 0.8520(2) 0.0298(10) Uani 1 1 d . . . H14A H 0.6810 0.4650 0.9005 0.036 Uiso 1 1 calc R . . C15 C 0.5143(5) 0.2592(5) 0.8396(2) 0.0303(10) Uani 1 1 d . . . C16 C 0.4568(5) 0.1911(5) 0.7669(2) 0.0304(10) Uani 1 1 d . . . H16A H 0.3745 0.0812 0.7586 0.036 Uiso 1 1 calc R . . O3 O 0.8382(4) 0.6709(3) 0.80801(17) 0.0333(7) Uani 1 1 d . . . C17 C 0.9189(6) 0.7683(6) 0.7469(3) 0.0376(11) Uani 1 1 d . . . H17A H 1.0077 0.8741 0.7656 0.056 Uiso 1 1 calc R . . H17B H 0.8270 0.7877 0.7182 0.056 Uiso 1 1 calc R . . H17C H 0.9766 0.7088 0.7155 0.056 Uiso 1 1 calc R . . O4 O 0.4389(4) 0.1553(4) 0.89555(17) 0.0375(8) Uani 1 1 d . . . C18 C 0.4915(6) 0.2201(6) 0.9708(3) 0.0378(11) Uani 1 1 d . . . H18A H 0.4261 0.1371 1.0047 0.057 Uiso 1 1 calc R . . H18B H 0.4644 0.3196 0.9806 0.057 Uiso 1 1 calc R . . H18C H 0.6193 0.2474 0.9780 0.057 Uiso 1 1 calc R . . B1 B -0.5840(12) -0.2104(10) 0.6276(5) 0.072(3) Uani 1 1 d . . . F1 F -0.6153(7) -0.3788(4) 0.6230(2) 0.0860(12) Uani 1 1 d . . . F2 F -0.7400(4) -0.1867(5) 0.65045(19) 0.0700(10) Uani 1 1 d . . . F3 F -0.4461(5) -0.1254(4) 0.6798(3) 0.1064(18) Uani 1 1 d . . . F4 F -0.5381(8) -0.1438(7) 0.5586(3) 0.155(3) Uani 1 1 d . . . O20 O 0.7652(9) 0.3031(9) 0.5510(4) 0.0446(16) Uani 0.50 1 d P . . C20 C 1.0147(17) 0.4391(18) 0.4753(7) 0.068(4) Uani 0.50 1 d P . . C21 C 0.8532(16) 0.4283(13) 0.5201(5) 0.050(3) Uani 0.50 1 d P . . C22 C 0.796(3) 0.5731(17) 0.5234(7) 0.115(8) Uani 0.50 1 d P . . 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 0.0141(4) 0.0298(5) 0.0285(4) -0.0038(3) -0.0023(3) 0.0058(3) N1 0.0119(16) 0.036(2) 0.0297(19) -0.0024(15) -0.0037(13) 0.0050(15) C1 0.0154(18) 0.021(2) 0.027(2) 0.0012(16) -0.0041(15) 0.0059(16) N2 0.0171(17) 0.032(2) 0.028(2) -0.0063(16) -0.0046(15) 0.0079(15) C2 0.0155(19) 0.022(2) 0.034(2) -0.0015(17) -0.0041(16) 0.0051(16) N3 0.0141(17) 0.040(2) 0.033(2) -0.0080(16) -0.0003(15) 0.0080(16) N4 0.0138(17) 0.033(2) 0.0286(19) -0.0039(15) -0.0037(14) 0.0076(16) C3 0.0187(19) 0.029(2) 0.030(2) -0.0040(17) -0.0024(16) 0.0132(18) C4 0.021(2) 0.027(2) 0.033(2) -0.0006(17) -0.0019(17) 0.0110(18) C5 0.021(2) 0.026(2) 0.043(3) -0.0091(19) -0.0072(18) 0.0118(18) C6 0.024(2) 0.031(2) 0.031(2) -0.0094(18) -0.0069(17) 0.0153(19) C7 0.022(2) 0.031(2) 0.033(2) -0.0026(18) 0.0035(17) 0.0147(18) C8 0.0162(19) 0.027(2) 0.031(2) -0.0080(17) 0.0004(16) 0.0088(17) O1 0.0286(16) 0.0248(16) 0.0486(19) -0.0089(14) -0.0079(14) 0.0043(13) C9 0.031(2) 0.030(2) 0.057(3) -0.002(2) -0.002(2) 0.008(2) O2 0.0295(16) 0.0410(18) 0.0266(15) -0.0047(13) 0.0028(12) 0.0118(14) C10 0.040(3) 0.047(3) 0.027(2) -0.007(2) 0.0002(19) 0.020(2) N5 0.0165(18) 0.036(2) 0.035(2) -0.0067(17) -0.0013(16) 0.0070(16) C11 0.0159(19) 0.030(2) 0.037(2) -0.0051(19) -0.0064(17) 0.0108(17) C12 0.0167(19) 0.027(2) 0.039(2) -0.0004(18) -0.0028(17) 0.0082(17) C13 0.018(2) 0.026(2) 0.043(3) -0.0053(19) -0.0029(17) 0.0113(18) C14 0.023(2) 0.029(2) 0.038(2) -0.0050(19) -0.0106(18) 0.0120(18) C15 0.020(2) 0.029(2) 0.043(3) 0.001(2) -0.0095(18) 0.0102(18) C16 0.018(2) 0.023(2) 0.047(3) -0.0029(19) -0.0107(18) 0.0052(17) O3 0.0285(16) 0.0234(16) 0.0410(18) -0.0053(13) -0.0042(13) 0.0027(13) C17 0.030(2) 0.031(2) 0.043(3) -0.003(2) 0.007(2) 0.003(2) O4 0.0342(17) 0.0321(17) 0.0406(18) 0.0051(14) -0.0112(14) 0.0054(14) C18 0.033(2) 0.037(3) 0.042(3) 0.003(2) -0.006(2) 0.010(2) B1 0.081(6) 0.063(5) 0.098(6) 0.047(4) 0.055(5) 0.051(5) F1 0.132(4) 0.053(2) 0.079(3) 0.0003(18) -0.023(2) 0.043(2) F2 0.0416(17) 0.095(3) 0.077(2) 0.036(2) 0.0334(16) 0.0257(18) F3 0.0285(18) 0.044(2) 0.234(6) 0.006(3) 0.043(3) -0.0013(16) F4 0.189(5) 0.193(5) 0.181(5) 0.152(5) 0.167(5) 0.164(5) O20 0.043(4) 0.050(4) 0.041(4) 0.013(3) 0.014(3) 0.016(3) C20 0.048(7) 0.081(10) 0.053(7) 0.007(6) 0.008(6) -0.003(7) C21 0.065(7) 0.040(6) 0.032(5) 0.007(5) -0.004(5) 0.005(6) C22 0.27(3) 0.052(8) 0.047(8) -0.005(6) -0.044(11) 0.088(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.857(3) . ? Ni1 N1 1.857(3) 2_556 ? Ni1 N3 1.859(3) 2_556 ? Ni1 N3 1.859(3) . ? N1 C1 1.287(5) . ? N1 H1A 0.8600 . ? C1 N4 1.355(5) . ? C1 N2 1.363(5) . ? N2 C2 1.363(5) . ? N2 H2 0.75(5) . ? C2 N3 1.294(5) . ? C2 N5 1.360(5) . ? N3 H3 0.86(5) . ? N4 C3 1.427(5) . ? N4 H4 0.82(5) . ? C3 C8 1.382(6) . ? C3 C4 1.396(6) . ? C4 C5 1.384(6) . ? C4 H4A 0.9300 . ? C5 O1 1.363(5) . ? C5 C6 1.395(6) . ? C6 C7 1.375(6) . ? C6 H6A 0.9300 . ? C7 O2 1.359(5) . ? C7 C8 1.393(6) . ? C8 H8A 0.9300 . ? O1 C9 1.430(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? O2 C10 1.437(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N5 C11 1.421(5) . ? N5 H5 0.73(5) . ? C11 C16 1.372(6) . ? C11 C12 1.393(6) . ? C12 C13 1.379(6) . ? C12 H12A 0.9300 . ? C13 O3 1.370(5) . ? C13 C14 1.392(6) . ? C14 C15 1.381(6) . ? C14 H14A 0.9300 . ? C15 O4 1.367(5) . ? C15 C16 1.395(6) . ? C16 H16A 0.9300 . ? O3 C17 1.421(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O4 C18 1.424(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? B1 F1 1.369(8) . ? B1 F4 1.383(8) . ? B1 F2 1.384(7) . ? B1 F3 1.386(11) . ? O20 C21 1.210(12) . ? C20 C21 1.227(16) 2_766 ? C20 C20 1.41(3) 2_766 ? C20 C21 1.489(17) . ? C20 C22 1.54(2) 2_766 ? C21 C20 1.227(16) 2_766 ? C21 C22 1.469(18) . ? C22 C20 1.54(2) 2_766 ? 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 N1 180.00(11) . 2_556 ? N1 Ni1 N3 89.70(15) . 2_556 ? N1 Ni1 N3 90.30(15) 2_556 2_556 ? N1 Ni1 N3 90.30(15) . . ? N1 Ni1 N3 89.70(15) 2_556 . ? N3 Ni1 N3 180.000(1) 2_556 . ? C1 N1 Ni1 130.5(3) . . ? C1 N1 H1A 114.8 . . ? Ni1 N1 H1A 114.8 . . ? N1 C1 N4 122.8(3) . . ? N1 C1 N2 120.9(4) . . ? N4 C1 N2 116.2(3) . . ? C1 N2 C2 126.5(4) . . ? C1 N2 H2 117(4) . . ? C2 N2 H2 116(4) . . ? N3 C2 N5 123.1(4) . . ? N3 C2 N2 121.3(4) . . ? N5 C2 N2 115.5(4) . . ? C2 N3 Ni1 129.9(3) . . ? C2 N3 H3 112(3) . . ? Ni1 N3 H3 118(3) . . ? C1 N4 C3 126.1(3) . . ? C1 N4 H4 114(3) . . ? C3 N4 H4 116(3) . . ? C8 C3 C4 121.4(4) . . ? C8 C3 N4 118.2(4) . . ? C4 C3 N4 120.4(4) . . ? C5 C4 C3 118.1(4) . . ? C5 C4 H4A 120.9 . . ? C3 C4 H4A 120.9 . . ? O1 C5 C4 124.4(4) . . ? O1 C5 C6 114.3(4) . . ? C4 C5 C6 121.3(4) . . ? C7 C6 C5 119.4(4) . . ? C7 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? O2 C7 C6 124.0(4) . . ? O2 C7 C8 115.5(4) . . ? C6 C7 C8 120.5(4) . . ? C3 C8 C7 119.2(4) . . ? C3 C8 H8A 120.4 . . ? C7 C8 H8A 120.4 . . ? C5 O1 C9 117.8(3) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 O2 C10 117.4(3) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 N5 C11 125.0(4) . . ? C2 N5 H5 116(4) . . ? C11 N5 H5 119(4) . . ? C16 C11 C12 122.0(4) . . ? C16 C11 N5 120.2(4) . . ? C12 C11 N5 117.7(4) . . ? C13 C12 C11 117.7(4) . . ? C13 C12 H12A 121.1 . . ? C11 C12 H12A 121.1 . . ? O3 C13 C12 123.4(4) . . ? O3 C13 C14 114.6(4) . . ? C12 C13 C14 121.9(4) . . ? C15 C14 C13 118.7(4) . . ? C15 C14 H14A 120.7 . . ? C13 C14 H14A 120.7 . . ? O4 C15 C14 123.8(4) . . ? O4 C15 C16 115.5(4) . . ? C14 C15 C16 120.8(4) . . ? C11 C16 C15 118.8(4) . . ? C11 C16 H16A 120.6 . . ? C15 C16 H16A 120.6 . . ? C13 O3 C17 116.7(3) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 O4 C18 117.5(3) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? F1 B1 F4 110.8(7) . . ? F1 B1 F2 109.3(6) . . ? F4 B1 F2 108.4(5) . . ? F1 B1 F3 110.5(6) . . ? F4 B1 F3 109.4(7) . . ? F2 B1 F3 108.4(6) . . ? C21 C20 C20 68.2(11) 2_766 2_766 ? C21 C20 C21 118.2(12) 2_766 . ? C20 C20 C21 50.0(9) 2_766 . ? C21 C20 C22 62.8(10) 2_766 2_766 ? C20 C20 C22 118.1(14) 2_766 2_766 ? C21 C20 C22 145.4(12) . 2_766 ? O20 C21 C20 146.0(11) . 2_766 ? O20 C21 C22 119.7(13) . . ? C20 C21 C22 69.1(12) 2_766 . ? O20 C21 C20 122.2(11) . . ? C20 C21 C20 61.8(12) 2_766 . ? C22 C21 C20 118.0(14) . . ? C21 C22 C20 48.0(9) . 2_766 ? 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 N1 C1 -111(100) 2_556 . . . ? N3 Ni1 N1 C1 -171.8(4) 2_556 . . . ? N3 Ni1 N1 C1 8.2(4) . . . . ? Ni1 N1 C1 N4 173.3(3) . . . . ? Ni1 N1 C1 N2 -6.6(6) . . . . ? N1 C1 N2 C2 -1.6(6) . . . . ? N4 C1 N2 C2 178.4(4) . . . . ? C1 N2 C2 N3 5.4(7) . . . . ? C1 N2 C2 N5 -176.3(4) . . . . ? N5 C2 N3 Ni1 -179.2(3) . . . . ? N2 C2 N3 Ni1 -0.9(6) . . . . ? N1 Ni1 N3 C2 -4.3(4) . . . . ? N1 Ni1 N3 C2 175.7(4) 2_556 . . . ? N3 Ni1 N3 C2 147(100) 2_556 . . . ? N1 C1 N4 C3 170.5(4) . . . . ? N2 C1 N4 C3 -9.5(6) . . . . ? C1 N4 C3 C8 -120.9(4) . . . . ? C1 N4 C3 C4 61.4(5) . . . . ? C8 C3 C4 C5 2.5(6) . . . . ? N4 C3 C4 C5 -179.9(3) . . . . ? C3 C4 C5 O1 179.0(3) . . . . ? C3 C4 C5 C6 -2.6(6) . . . . ? O1 C5 C6 C7 179.2(3) . . . . ? C4 C5 C6 C7 0.7(6) . . . . ? C5 C6 C7 O2 -179.0(3) . . . . ? C5 C6 C7 C8 1.4(6) . . . . ? C4 C3 C8 C7 -0.4(6) . . . . ? N4 C3 C8 C7 -178.1(3) . . . . ? O2 C7 C8 C3 178.9(3) . . . . ? C6 C7 C8 C3 -1.6(6) . . . . ? C4 C5 O1 C9 0.1(6) . . . . ? C6 C5 O1 C9 -178.4(3) . . . . ? C6 C7 O2 C10 -4.1(5) . . . . ? C8 C7 O2 C10 175.5(3) . . . . ? N3 C2 N5 C11 -172.3(4) . . . . ? N2 C2 N5 C11 9.4(6) . . . . ? C2 N5 C11 C16 54.8(6) . . . . ? C2 N5 C11 C12 -125.1(4) . . . . ? C16 C11 C12 C13 -0.4(6) . . . . ? N5 C11 C12 C13 179.5(3) . . . . ? C11 C12 C13 O3 -180.0(3) . . . . ? C11 C12 C13 C14 -2.1(6) . . . . ? O3 C13 C14 C15 -179.8(3) . . . . ? C12 C13 C14 C15 2.1(6) . . . . ? C13 C14 C15 O4 178.9(4) . . . . ? C13 C14 C15 C16 0.4(6) . . . . ? C12 C11 C16 C15 2.8(6) . . . . ? N5 C11 C16 C15 -177.1(4) . . . . ? O4 C15 C16 C11 178.6(3) . . . . ? C14 C15 C16 C11 -2.7(6) . . . . ? C12 C13 O3 C17 -4.5(5) . . . . ? C14 C13 O3 C17 177.4(3) . . . . ? C14 C15 O4 C18 2.3(6) . . . . ? C16 C15 O4 C18 -179.1(4) . . . . ? C21 C20 C21 O20 -140.7(15) 2_766 . . . ? C20 C20 C21 O20 -140.7(15) 2_766 . . . ? C22 C20 C21 O20 -58(3) 2_766 . . . ? C21 C20 C21 C20 0.000(2) 2_766 . . 2_766 ? C22 C20 C21 C20 82(2) 2_766 . . 2_766 ? C21 C20 C21 C22 42.0(14) 2_766 . . . ? C20 C20 C21 C22 42.0(14) 2_766 . . . ? C22 C20 C21 C22 124.3(18) 2_766 . . . ? O20 C21 C22 C20 143.5(13) . . . 2_766 ? C20 C21 C22 C20 -39.1(13) . . . 2_766 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F3 0.86 2.42 3.111(5) 137.8 . N1 H1A F4 0.86 2.46 3.293(7) 164.7 . N3 H3 F4 0.86(5) 2.13(5) 2.956(5) 160(4) 2_556 N4 H4 F3 0.82(5) 2.16(5) 2.893(5) 149(4) . N5 H5 O20 0.73(5) 2.01(5) 2.714(7) 161(5) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.79 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.292 _refine_diff_density_min -1.230 _refine_diff_density_rms 0.092 data_dma47 _database_code_depnum_ccdc_archive 'CCDC 843771' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N5 O4' _chemical_formula_sum 'C18 H23 N5 O4' _chemical_formula_weight 373.41 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.961(2) _cell_length_b 10.019(2) _cell_length_c 10.989(2) _cell_angle_alpha 75.650(11) _cell_angle_beta 75.016(11) _cell_angle_gamma 80.808(13) _cell_volume 918.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 5176 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.17 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88666 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 31150 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.55 _reflns_number_total 4201 _reflns_number_gt 3018 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^)+(0.0614P)^2^+0.0990P] 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 4201 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 N1 N 0.18329(17) 0.83184(15) -0.04082(13) 0.0285(3) Uani 1 1 d . . . H1A H 0.235(2) 0.8917(18) -0.1076(17) 0.031(5) Uiso 1 1 d . . . H1B H 0.110(2) 0.7878(18) -0.0492(16) 0.029(5) Uiso 1 1 d . . . C1 C 0.21937(16) 0.80952(15) 0.07574(13) 0.0178(3) Uani 1 1 d . . . N2 N 0.33027(13) 0.88953(12) 0.07563(11) 0.0176(3) Uani 1 1 d . . . C2 C 0.38181(16) 0.87968(14) 0.18204(13) 0.0170(3) Uani 1 1 d . . . N3 N 0.48786(15) 0.96556(13) 0.17270(13) 0.0203(3) Uani 1 1 d . . . H3A H 0.542(2) 1.0071(19) 0.094(2) 0.041(5) Uiso 1 1 d . . . H3B H 0.540(2) 0.9465(17) 0.2354(17) 0.031(5) Uiso 1 1 d . . . N4 N 0.15740(13) 0.71644(12) 0.17614(11) 0.0187(3) Uani 1 1 d . . . C3 C 0.04992(16) 0.63109(15) 0.16756(13) 0.0174(3) Uani 1 1 d . . . C4 C 0.09031(16) 0.48766(15) 0.19403(13) 0.0185(3) Uani 1 1 d . . . H4 H 0.1862 0.4512 0.2124 0.022 Uiso 1 1 calc R . . C5 C -0.01492(17) 0.40087(15) 0.19243(14) 0.0203(3) Uani 1 1 d . . . C6 C -0.16180(17) 0.45297(15) 0.17076(13) 0.0206(3) Uani 1 1 d . . . H6 H -0.2334 0.3934 0.1746 0.025 Uiso 1 1 calc R . . C7 C -0.19904(16) 0.59450(15) 0.14351(13) 0.0192(3) Uani 1 1 d . . . C8 C -0.09416(16) 0.68478(15) 0.14102(13) 0.0190(3) Uani 1 1 d . . . H8 H -0.1204 0.7801 0.1218 0.023 Uiso 1 1 calc R . . O1 O 0.01458(12) 0.25948(10) 0.21037(11) 0.0271(3) Uani 1 1 d . . . C9 C 0.17045(18) 0.20046(17) 0.21314(17) 0.0298(4) Uani 1 1 d . . . H9A H 0.2404 0.2438 0.1366 0.045 Uiso 1 1 calc R . . H9B H 0.1786 0.1029 0.2169 0.045 Uiso 1 1 calc R . . H9C H 0.1969 0.2151 0.2878 0.045 Uiso 1 1 calc R . . O2 O -0.33818(11) 0.65625(11) 0.11670(10) 0.0257(3) Uani 1 1 d . . . C10 C -0.44186(19) 0.56719(18) 0.10677(18) 0.0333(4) Uani 1 1 d . . . H10A H -0.3892 0.5120 0.0453 0.050 Uiso 1 1 calc R . . H10B H -0.5299 0.6220 0.0788 0.050 Uiso 1 1 calc R . . H10C H -0.4762 0.5077 0.1895 0.050 Uiso 1 1 calc R . . N5 N 0.33126(14) 0.79475(13) 0.29570(11) 0.0190(3) Uani 1 1 d . . . H5 H 0.255(2) 0.744(2) 0.296(2) 0.062(7) Uiso 1 1 d . . . C11 C 0.38180(16) 0.79595(15) 0.40864(13) 0.0177(3) Uani 1 1 d . . . C12 C 0.51163(17) 0.71090(15) 0.43717(13) 0.0201(3) Uani 1 1 d . . . H12 H 0.5674 0.6526 0.3834 0.024 Uiso 1 1 calc R . . C13 C 0.55678(17) 0.71473(15) 0.54861(13) 0.0203(3) Uani 1 1 d . . . C14 C 0.47509(17) 0.80410(16) 0.62738(14) 0.0206(3) Uani 1 1 d . . . H14 H 0.5063(17) 0.8058(16) 0.7026(16) 0.022(4) Uiso 1 1 d . . . C15 C 0.34725(16) 0.88997(15) 0.59578(13) 0.0187(3) Uani 1 1 d . . . C16 C 0.29835(17) 0.88587(15) 0.48604(13) 0.0186(3) Uani 1 1 d . . . H16 H 0.2115 0.9423 0.4652 0.022 Uiso 1 1 calc R . . O3 O 0.68186(12) 0.63523(11) 0.58801(10) 0.0265(3) Uani 1 1 d . . . C17 C 0.77446(18) 0.54494(17) 0.50791(15) 0.0259(4) Uani 1 1 d . . . H17A H 0.7106 0.4815 0.4985 0.039 Uiso 1 1 calc R . . H17B H 0.8566 0.4940 0.5471 0.039 Uiso 1 1 calc R . . H17C H 0.8182 0.5989 0.4245 0.039 Uiso 1 1 calc R . . O4 O 0.27573(12) 0.97790(11) 0.67678(9) 0.0234(3) Uani 1 1 d . . . C18 C 0.13909(18) 1.06337(17) 0.64810(16) 0.0281(4) Uani 1 1 d . . . H18A H 0.1656 1.1239 0.5647 0.042 Uiso 1 1 calc R . . H18B H 0.0972 1.1176 0.7123 0.042 Uiso 1 1 calc R . . H18C H 0.0631 1.0058 0.6481 0.042 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 N1 0.0369(8) 0.0371(9) 0.0176(7) 0.0014(6) -0.0122(6) -0.0230(7) C1 0.0182(7) 0.0202(8) 0.0179(7) -0.0071(6) -0.0066(6) -0.0020(6) N2 0.0212(7) 0.0184(6) 0.0161(6) -0.0029(5) -0.0080(5) -0.0053(5) C2 0.0174(7) 0.0154(7) 0.0194(7) -0.0052(6) -0.0056(6) -0.0012(6) N3 0.0260(7) 0.0227(7) 0.0155(6) -0.0010(5) -0.0094(6) -0.0096(6) N4 0.0203(6) 0.0202(7) 0.0182(6) -0.0035(5) -0.0070(5) -0.0062(5) C3 0.0188(7) 0.0234(8) 0.0113(7) -0.0043(6) -0.0032(6) -0.0059(6) C4 0.0166(7) 0.0226(8) 0.0174(7) -0.0031(6) -0.0069(6) -0.0022(6) C5 0.0233(8) 0.0193(8) 0.0198(7) -0.0050(6) -0.0060(6) -0.0032(6) C6 0.0191(8) 0.0232(8) 0.0232(8) -0.0080(6) -0.0058(6) -0.0065(6) C7 0.0169(7) 0.0263(8) 0.0171(7) -0.0092(6) -0.0060(6) -0.0003(6) C8 0.0214(8) 0.0190(8) 0.0189(7) -0.0058(6) -0.0067(6) -0.0024(6) O1 0.0244(6) 0.0182(6) 0.0419(7) -0.0055(5) -0.0138(5) -0.0031(5) C9 0.0258(9) 0.0221(9) 0.0437(10) -0.0051(7) -0.0152(8) 0.0005(7) O2 0.0193(6) 0.0263(6) 0.0387(6) -0.0138(5) -0.0139(5) -0.0001(5) C10 0.0217(8) 0.0351(10) 0.0544(11) -0.0231(9) -0.0187(8) 0.0017(7) N5 0.0221(7) 0.0228(7) 0.0152(6) -0.0028(5) -0.0083(5) -0.0069(6) C11 0.0221(8) 0.0187(8) 0.0148(7) 0.0002(6) -0.0072(6) -0.0098(6) C12 0.0211(8) 0.0222(8) 0.0178(7) -0.0044(6) -0.0035(6) -0.0060(6) C13 0.0190(8) 0.0238(8) 0.0179(7) 0.0008(6) -0.0065(6) -0.0066(6) C14 0.0256(8) 0.0254(8) 0.0135(7) -0.0015(6) -0.0081(6) -0.0088(7) C15 0.0225(8) 0.0191(8) 0.0154(7) -0.0025(6) -0.0032(6) -0.0085(6) C16 0.0197(7) 0.0197(8) 0.0182(7) -0.0011(6) -0.0085(6) -0.0052(6) O3 0.0237(6) 0.0353(7) 0.0219(6) -0.0061(5) -0.0114(5) 0.0030(5) C17 0.0236(8) 0.0293(9) 0.0242(8) -0.0031(7) -0.0077(7) -0.0015(7) O4 0.0298(6) 0.0247(6) 0.0194(5) -0.0077(4) -0.0098(5) -0.0023(5) C18 0.0307(9) 0.0305(9) 0.0273(8) -0.0122(7) -0.0110(7) 0.0015(7) _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 N1 C1 1.3580(18) . ? N1 H1A 0.898(19) . ? N1 H1B 0.882(18) . ? C1 N4 1.3168(18) . ? C1 N2 1.3724(18) . ? N2 C2 1.3408(17) . ? C2 N5 1.3390(18) . ? C2 N3 1.3494(19) . ? N3 H3A 0.91(2) . ? N3 H3B 0.896(18) . ? N4 C3 1.4204(18) . ? C3 C8 1.3916(19) . ? C3 C4 1.401(2) . ? C4 C5 1.387(2) . ? C4 H4 0.9300 . ? C5 O1 1.3727(18) . ? C5 C6 1.394(2) . ? C6 C7 1.379(2) . ? C6 H6 0.9300 . ? C7 O2 1.3701(17) . ? C7 C8 1.396(2) . ? C8 H8 0.9300 . ? O1 C9 1.4320(18) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? O2 C10 1.4272(18) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N5 C11 1.4301(17) . ? N5 H5 0.92(2) . ? C11 C12 1.385(2) . ? C11 C16 1.389(2) . ? C12 C13 1.3961(19) . ? C12 H12 0.9300 . ? C13 O3 1.3686(17) . ? C13 C14 1.391(2) . ? C14 C15 1.384(2) . ? C14 H14 0.943(16) . ? C15 O4 1.3757(17) . ? C15 C16 1.3969(19) . ? C16 H16 0.9300 . ? O3 C17 1.4348(18) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O4 C18 1.4362(18) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C1 N1 H1A 118.9(11) . . ? C1 N1 H1B 119.5(11) . . ? H1A N1 H1B 121.6(15) . . ? N4 C1 N1 122.66(13) . . ? N4 C1 N2 124.24(12) . . ? N1 C1 N2 113.06(13) . . ? C2 N2 C1 121.25(12) . . ? N5 C2 N2 124.41(13) . . ? N5 C2 N3 118.98(13) . . ? N2 C2 N3 116.57(13) . . ? C2 N3 H3A 119.9(12) . . ? C2 N3 H3B 117.2(11) . . ? H3A N3 H3B 114.9(16) . . ? C1 N4 C3 121.39(11) . . ? C8 C3 C4 120.16(13) . . ? C8 C3 N4 122.36(13) . . ? C4 C3 N4 117.39(12) . . ? C5 C4 C3 118.95(13) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? O1 C5 C4 124.20(13) . . ? O1 C5 C6 114.35(13) . . ? C4 C5 C6 121.45(13) . . ? C7 C6 C5 118.76(13) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? O2 C7 C6 123.35(13) . . ? O2 C7 C8 115.53(13) . . ? C6 C7 C8 121.11(13) . . ? C3 C8 C7 119.47(13) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C5 O1 C9 117.43(12) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 O2 C10 116.71(11) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 N5 C11 122.01(12) . . ? C2 N5 H5 113.7(13) . . ? C11 N5 H5 123.9(13) . . ? C12 C11 C16 121.89(12) . . ? C12 C11 N5 120.17(13) . . ? C16 C11 N5 117.94(12) . . ? C11 C12 C13 118.40(13) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? O3 C13 C14 115.23(12) . . ? O3 C13 C12 124.09(13) . . ? C14 C13 C12 120.67(13) . . ? C15 C14 C13 119.94(13) . . ? C15 C14 H14 120.0(9) . . ? C13 C14 H14 120.1(9) . . ? O4 C15 C14 116.23(12) . . ? O4 C15 C16 123.46(13) . . ? C14 C15 C16 120.30(13) . . ? C11 C16 C15 118.78(13) . . ? C11 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C13 O3 C17 117.82(11) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 O4 C18 116.75(11) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 N4 C1 N2 C2 -1.5(2) . . . . ? N1 C1 N2 C2 -179.00(13) . . . . ? C1 N2 C2 N5 -0.6(2) . . . . ? C1 N2 C2 N3 -178.27(12) . . . . ? N1 C1 N4 C3 1.2(2) . . . . ? N2 C1 N4 C3 -176.12(12) . . . . ? C1 N4 C3 C8 -63.73(18) . . . . ? C1 N4 C3 C4 119.72(15) . . . . ? C8 C3 C4 C5 0.4(2) . . . . ? N4 C3 C4 C5 177.05(12) . . . . ? C3 C4 C5 O1 176.58(12) . . . . ? C3 C4 C5 C6 -2.9(2) . . . . ? O1 C5 C6 C7 -175.95(12) . . . . ? C4 C5 C6 C7 3.5(2) . . . . ? C5 C6 C7 O2 177.85(12) . . . . ? C5 C6 C7 C8 -1.8(2) . . . . ? C4 C3 C8 C7 1.25(19) . . . . ? N4 C3 C8 C7 -175.20(12) . . . . ? O2 C7 C8 C3 179.77(11) . . . . ? C6 C7 C8 C3 -0.6(2) . . . . ? C4 C5 O1 C9 -8.9(2) . . . . ? C6 C5 O1 C9 170.54(13) . . . . ? C6 C7 O2 C10 -5.31(19) . . . . ? C8 C7 O2 C10 174.36(13) . . . . ? N2 C2 N5 C11 -175.19(13) . . . . ? N3 C2 N5 C11 2.4(2) . . . . ? C2 N5 C11 C12 -90.35(17) . . . . ? C2 N5 C11 C16 88.66(17) . . . . ? C16 C11 C12 C13 1.3(2) . . . . ? N5 C11 C12 C13 -179.74(13) . . . . ? C11 C12 C13 O3 179.47(12) . . . . ? C11 C12 C13 C14 -1.4(2) . . . . ? O3 C13 C14 C15 179.50(12) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C13 C14 C15 O4 -178.22(13) . . . . ? C13 C14 C15 C16 1.0(2) . . . . ? C12 C11 C16 C15 -0.1(2) . . . . ? N5 C11 C16 C15 -179.10(12) . . . . ? O4 C15 C16 C11 178.08(12) . . . . ? C14 C15 C16 C11 -1.0(2) . . . . ? C14 C13 O3 C17 -177.56(12) . . . . ? C12 C13 O3 C17 1.6(2) . . . . ? C14 C15 O4 C18 -177.47(12) . . . . ? C16 C15 O4 C18 3.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5 N4 0.92(2) 1.85(2) 2.5940(17) 137.0(19) . N1 H1A O4 0.898(19) 2.265(18) 3.0438(18) 144.9(14) 1_554 N1 H1B O1 0.882(18) 2.493(18) 3.2441(17) 143.4(14) 2_565 N3 H3A N2 0.91(2) 2.04(2) 2.9501(19) 175.0(17) 2_675 N3 H3B O4 0.896(18) 2.412(18) 3.1944(16) 146.1(14) 2_676 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.266 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.053 data_dma34 _database_code_depnum_ccdc_archive 'CCDC 843772' #TrackingRef '7136_web_deposit_cif_file_3_DavidMcMorran_1315712607.dma34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H44 N10 Ni, 4(C2 H6 O S)' _chemical_formula_sum 'C44 H68 N10 Ni O4 S4' _chemical_formula_weight 988.03 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' S S 0.1246 0.1234 '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 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' _cell_length_a 8.701(5) _cell_length_b 11.840(5) _cell_length_c 13.424(5) _cell_angle_alpha 92.325(5) _cell_angle_beta 104.102(5) _cell_angle_gamma 110.911(5) _cell_volume 1240.4(10) _cell_formula_units_Z 1 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 7123 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 34.49 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 0.610 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76800 _exptl_absorpt_correction_T_max 0.92400 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 34673 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 34.89 _reflns_number_total 10423 _reflns_number_gt 8241 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0525P)^2^+0.1352P] 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 10423 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _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 0.0000 0.5000 0.0000 0.01045(5) Uani 1 2 d S . . N1 N -0.10853(12) 0.40010(9) -0.12661(8) 0.01374(19) Uani 1 1 d . . . H1 H -0.055(2) 0.4118(15) -0.1764(13) 0.024(4) Uiso 1 1 d . . . C1 C -0.26760(14) 0.31780(10) -0.16035(9) 0.0119(2) Uani 1 1 d . . . N2 N -0.38237(12) 0.28265(9) -0.10575(7) 0.01375(19) Uani 1 1 d . . . C2 C -0.34327(14) 0.34056(10) -0.00887(9) 0.0127(2) Uani 1 1 d . . . N3 N -0.19813(12) 0.42981(9) 0.04159(8) 0.01442(19) Uani 1 1 d . . . H3 H -0.203(2) 0.4560(16) 0.1007(14) 0.025(4) Uiso 1 1 d . . . N4 N -0.31730(12) 0.26131(10) -0.26174(8) 0.0154(2) Uani 1 1 d . . . H4 H -0.237(2) 0.2898(14) -0.2939(12) 0.019(4) Uiso 1 1 d . . . C3 C -0.47411(14) 0.17547(10) -0.32342(9) 0.0124(2) Uani 1 1 d . . . C4 C -0.60655(14) 0.10061(10) -0.28575(9) 0.0133(2) Uani 1 1 d . . . H4B H -0.5959 0.1072 -0.2149 0.016 Uiso 1 1 calc R . . C5 C -0.75499(14) 0.01584(10) -0.35532(9) 0.0136(2) Uani 1 1 d . . . C6 C -0.77000(15) 0.00532(10) -0.46165(9) 0.0148(2) Uani 1 1 d . . . H6A H -0.8692 -0.0512 -0.5073 0.018 Uiso 1 1 calc R . . C7 C -0.63826(14) 0.07840(10) -0.50031(9) 0.0129(2) Uani 1 1 d . . . C8 C -0.49171(14) 0.16289(10) -0.43076(9) 0.0130(2) Uani 1 1 d . . . H8A H -0.4033 0.2122 -0.4557 0.016 Uiso 1 1 calc R . . C9 C -0.89597(16) -0.06485(11) -0.31353(10) 0.0190(2) Uani 1 1 d . . . H9A H -0.9888 -0.1177 -0.3700 0.028 Uiso 1 1 calc R . . H9B H -0.9361 -0.0150 -0.2767 0.028 Uiso 1 1 calc R . . H9C H -0.8528 -0.1131 -0.2673 0.028 Uiso 1 1 calc R . . C10 C -0.65462(16) 0.06681(11) -0.61535(9) 0.0169(2) Uani 1 1 d . . . H10A H -0.5528 0.1238 -0.6277 0.025 Uiso 0.228(18) 1 calc PR A 1 H10B H -0.7518 0.0840 -0.6514 0.025 Uiso 0.228(18) 1 calc PR A 1 H10C H -0.6697 -0.0147 -0.6400 0.025 Uiso 0.228(18) 1 calc PR A 1 H10D H -0.7438 -0.0046 -0.6506 0.008(5) Uiso 0.772(18) 1 d PR A 2 H10E H -0.5389 0.0659 -0.6262 0.013(5) Uiso 0.772(18) 1 d PR A 2 H10F H -0.6782 0.1381 -0.6508 0.013(5) Uiso 0.772(18) 1 d PR A 2 N5 N -0.47740(13) 0.29733(10) 0.03474(8) 0.0174(2) Uani 1 1 d . . . H5 H -0.570(2) 0.2441(14) -0.0061(12) 0.018(4) Uiso 1 1 d . . . C11 C -0.47195(14) 0.32610(10) 0.13931(9) 0.0146(2) Uani 1 1 d . . . C12 C -0.33790(15) 0.32550(11) 0.22127(9) 0.0166(2) Uani 1 1 d . . . H12A H -0.2492 0.3073 0.2072 0.020 Uiso 1 1 calc R . . C13 C -0.33546(16) 0.35199(11) 0.32417(9) 0.0177(2) Uani 1 1 d . . . C14 C -0.47162(16) 0.37517(11) 0.34342(9) 0.0186(2) Uani 1 1 d . . . H14A H -0.4717 0.3917 0.4117 0.022 Uiso 1 1 calc R . . C15 C -0.60863(16) 0.37444(11) 0.26306(10) 0.0178(2) Uani 1 1 d . . . C16 C -0.60674(15) 0.35090(11) 0.16089(9) 0.0168(2) Uani 1 1 d . . . H16A H -0.6960 0.3517 0.1066 0.020 Uiso 1 1 calc R . . C17 C -0.18749(18) 0.35361(14) 0.41102(11) 0.0262(3) Uani 1 1 d . . . H17A H -0.2051 0.3731 0.4764 0.039 Uiso 1 1 calc R . . H17B H -0.0832 0.4140 0.4046 0.039 Uiso 1 1 calc R . . H17C H -0.1797 0.2747 0.4074 0.039 Uiso 1 1 calc R . . C18 C -0.7553(2) 0.39955(14) 0.28692(12) 0.0266(3) Uani 1 1 d . . . H18A H -0.7355 0.4135 0.3607 0.040 Uiso 0.228(18) 1 calc PR A 1 H18B H -0.8602 0.3305 0.2575 0.040 Uiso 0.228(18) 1 calc PR A 1 H18C H -0.7636 0.4705 0.2577 0.040 Uiso 0.228(18) 1 calc PR A 1 H18D H -0.8362 0.4059 0.2204 0.020(6) Uiso 0.772(18) 1 d PR A 2 H18E H -0.8137 0.3271 0.3295 0.038(7) Uiso 0.772(18) 1 d PR A 2 H18F H -0.7097 0.4638 0.3176 0.033(7) Uiso 0.772(18) 1 d PR A 2 S1 S 0.07801(4) 0.27205(3) -0.32013(2) 0.01861(7) Uani 1 1 d . . . O1 O -0.01339(12) 0.35987(10) -0.32751(7) 0.0233(2) Uani 1 1 d . . . C20 C 0.25190(19) 0.33039(14) -0.20485(11) 0.0265(3) Uani 1 1 d . . . H20A H 0.2083 0.3189 -0.1453 0.040 Uiso 1 1 calc R . . H20B H 0.3132 0.4159 -0.2043 0.040 Uiso 1 1 calc R . . H20C H 0.3277 0.2877 -0.2030 0.040 Uiso 1 1 calc R . . C21 C 0.19746(17) 0.30618(12) -0.41327(11) 0.0210(3) Uani 1 1 d . . . H21A H 0.1205 0.2797 -0.4819 0.032 Uiso 1 1 calc R . . H21B H 0.2755 0.2645 -0.4034 0.032 Uiso 1 1 calc R . . H21C H 0.2607 0.3926 -0.4047 0.032 Uiso 1 1 calc R . . S2 S -0.74319(4) -0.02582(3) -0.01835(3) 0.02289(8) Uani 1 1 d . . . O2 O -0.78971(12) 0.07886(8) -0.05772(7) 0.0232(2) Uani 1 1 d . . . C30 C -0.7079(3) -0.00412(15) 0.11917(13) 0.0426(5) Uani 1 1 d . . . H30A H -0.6039 0.0651 0.1498 0.064 Uiso 1 1 calc R . . H30B H -0.6988 -0.0757 0.1468 0.064 Uiso 1 1 calc R . . H30C H -0.8022 0.0100 0.1347 0.064 Uiso 1 1 calc R . . C31 C -0.93824(17) -0.15637(12) -0.04656(12) 0.0244(3) Uani 1 1 d . . . H31A H -0.9791 -0.1830 -0.1200 0.037 Uiso 1 1 calc R . . H31B H -1.0222 -0.1355 -0.0237 0.037 Uiso 1 1 calc R . . H31C H -0.9184 -0.2209 -0.0112 0.037 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 0.00908(9) 0.01020(9) 0.00873(9) -0.00151(7) 0.00142(7) 0.00076(7) N1 0.0109(4) 0.0147(4) 0.0116(4) -0.0020(3) 0.0033(3) 0.0003(3) C1 0.0118(4) 0.0111(5) 0.0111(5) 0.0000(4) 0.0017(4) 0.0035(4) N2 0.0117(4) 0.0152(4) 0.0105(4) -0.0023(3) 0.0023(3) 0.0016(3) C2 0.0106(4) 0.0128(5) 0.0126(5) 0.0005(4) 0.0025(4) 0.0027(4) N3 0.0119(4) 0.0150(4) 0.0113(4) -0.0043(3) 0.0031(3) -0.0002(3) N4 0.0109(4) 0.0195(5) 0.0102(4) -0.0036(4) 0.0026(3) 0.0001(3) C3 0.0105(4) 0.0120(5) 0.0119(5) -0.0026(4) 0.0008(4) 0.0032(4) C4 0.0129(4) 0.0137(5) 0.0112(5) -0.0009(4) 0.0027(4) 0.0032(4) C5 0.0129(4) 0.0130(5) 0.0123(5) 0.0001(4) 0.0023(4) 0.0029(4) C6 0.0136(5) 0.0131(5) 0.0132(5) -0.0017(4) 0.0008(4) 0.0021(4) C7 0.0137(5) 0.0129(5) 0.0107(5) -0.0012(4) 0.0011(4) 0.0052(4) C8 0.0125(4) 0.0133(5) 0.0112(5) -0.0003(4) 0.0026(4) 0.0032(4) C9 0.0165(5) 0.0176(5) 0.0172(6) 0.0001(4) 0.0047(4) 0.0001(4) C10 0.0191(5) 0.0173(5) 0.0105(5) -0.0009(4) 0.0021(4) 0.0041(4) N5 0.0115(4) 0.0208(5) 0.0126(4) -0.0035(4) 0.0037(3) -0.0020(4) C11 0.0137(5) 0.0140(5) 0.0119(5) -0.0008(4) 0.0041(4) 0.0002(4) C12 0.0161(5) 0.0163(5) 0.0159(5) 0.0009(4) 0.0046(4) 0.0043(4) C13 0.0195(5) 0.0163(5) 0.0134(5) 0.0032(4) 0.0027(4) 0.0032(4) C14 0.0250(6) 0.0160(5) 0.0136(5) 0.0011(4) 0.0080(5) 0.0047(5) C15 0.0196(5) 0.0152(5) 0.0188(6) 0.0022(4) 0.0095(4) 0.0043(4) C16 0.0150(5) 0.0175(5) 0.0154(5) 0.0019(4) 0.0044(4) 0.0033(4) C17 0.0247(6) 0.0329(7) 0.0165(6) 0.0065(5) 0.0011(5) 0.0082(6) C18 0.0289(7) 0.0296(7) 0.0276(7) 0.0046(6) 0.0151(6) 0.0135(6) S1 0.01736(13) 0.01680(14) 0.01691(15) 0.00115(11) 0.00347(11) 0.00190(11) O1 0.0176(4) 0.0357(6) 0.0211(5) 0.0068(4) 0.0077(4) 0.0135(4) C20 0.0288(7) 0.0300(7) 0.0200(6) -0.0047(5) -0.0026(5) 0.0175(6) C21 0.0221(6) 0.0210(6) 0.0229(6) 0.0017(5) 0.0089(5) 0.0098(5) S2 0.01607(14) 0.02005(15) 0.02852(18) -0.00150(13) 0.00393(12) 0.00417(11) O2 0.0235(5) 0.0189(4) 0.0202(5) 0.0031(4) 0.0031(4) 0.0017(4) C30 0.0643(12) 0.0240(8) 0.0243(8) 0.0011(6) -0.0143(8) 0.0167(8) C31 0.0214(6) 0.0181(6) 0.0286(7) 0.0026(5) 0.0043(5) 0.0033(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.8539(11) 2_565 ? Ni1 N1 1.8539(11) . ? Ni1 N3 1.8596(13) 2_565 ? Ni1 N3 1.8596(13) . ? N1 C1 1.3290(15) . ? N1 H1 0.895(17) . ? C1 N2 1.3389(15) . ? C1 N4 1.3854(15) . ? N2 C2 1.3501(15) . ? C2 N3 1.3201(15) . ? C2 N5 1.3774(15) . ? N3 H3 0.855(17) . ? N4 C3 1.4041(15) . ? N4 H4 0.880(16) . ? C3 C4 1.4002(16) . ? C3 C8 1.4073(17) . ? C4 C5 1.3994(16) . ? C4 H4B 0.9300 . ? C5 C6 1.3975(17) . ? C5 C9 1.5082(17) . ? C6 C7 1.3965(16) . ? C6 H6A 0.9300 . ? C7 C8 1.3899(16) . ? C7 C10 1.5119(17) . ? C8 H8A 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C10 H10D 0.9280 . ? C10 H10E 1.0552 . ? C10 H10F 1.0444 . ? N5 C11 1.4164(16) . ? N5 H5 0.861(16) . ? C11 C16 1.3965(18) . ? C11 C12 1.3972(18) . ? C12 C13 1.3974(18) . ? C12 H12A 0.9300 . ? C13 C14 1.386(2) . ? C13 C17 1.505(2) . ? C14 C15 1.3965(19) . ? C14 H14A 0.9300 . ? C15 C16 1.3937(18) . ? C15 C18 1.511(2) . ? C16 H16A 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C18 H18D 1.0173 . ? C18 H18E 1.0912 . ? C18 H18F 0.7654 . ? S1 O1 1.5112(12) . ? S1 C21 1.7835(14) . ? S1 C20 1.7854(15) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? S2 O2 1.5120(12) . ? S2 C31 1.7831(15) . ? S2 C30 1.7881(18) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? 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 N1 180.00(6) 2_565 . ? N1 Ni1 N3 89.36(5) 2_565 2_565 ? N1 Ni1 N3 90.64(5) . 2_565 ? N1 Ni1 N3 90.64(5) 2_565 . ? N1 Ni1 N3 89.36(5) . . ? N3 Ni1 N3 180.00(8) 2_565 . ? C1 N1 Ni1 129.00(8) . . ? C1 N1 H1 112.1(11) . . ? Ni1 N1 H1 118.5(11) . . ? N1 C1 N2 126.60(11) . . ? N1 C1 N4 116.21(10) . . ? N2 C1 N4 117.17(10) . . ? C1 N2 C2 119.15(10) . . ? N3 C2 N2 126.76(10) . . ? N3 C2 N5 121.35(11) . . ? N2 C2 N5 111.88(10) . . ? C2 N3 Ni1 128.88(9) . . ? C2 N3 H3 111.3(12) . . ? Ni1 N3 H3 119.8(12) . . ? C1 N4 C3 131.77(10) . . ? C1 N4 H4 112.8(11) . . ? C3 N4 H4 115.2(11) . . ? C4 C3 N4 125.14(11) . . ? C4 C3 C8 119.30(10) . . ? N4 C3 C8 115.51(10) . . ? C5 C4 C3 119.61(11) . . ? C5 C4 H4B 120.2 . . ? C3 C4 H4B 120.2 . . ? C6 C5 C4 120.10(10) . . ? C6 C5 C9 120.88(10) . . ? C4 C5 C9 119.01(11) . . ? C7 C6 C5 120.96(10) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C8 C7 C6 118.57(11) . . ? C8 C7 C10 120.53(10) . . ? C6 C7 C10 120.90(10) . . ? C7 C8 C3 121.45(10) . . ? C7 C8 H8A 119.3 . . ? C3 C8 H8A 119.3 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C10 H10D 111.4 . . ? H10A C10 H10D 136.6 . . ? H10B C10 H10D 69.4 . . ? H10C C10 H10D 42.2 . . ? C7 C10 H10E 108.4 . . ? H10A C10 H10E 42.6 . . ? H10B C10 H10E 139.4 . . ? H10C C10 H10E 70.2 . . ? H10D C10 H10E 109.0 . . ? C7 C10 H10F 113.8 . . ? H10A C10 H10F 68.8 . . ? H10B C10 H10F 42.1 . . ? H10C C10 H10F 134.4 . . ? H10D C10 H10F 106.2 . . ? H10E C10 H10F 107.8 . . ? C2 N5 C11 126.34(10) . . ? C2 N5 H5 114.6(10) . . ? C11 N5 H5 118.9(10) . . ? C16 C11 C12 119.39(11) . . ? C16 C11 N5 119.23(11) . . ? C12 C11 N5 121.34(11) . . ? C11 C12 C13 120.81(12) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C14 C13 C12 118.60(12) . . ? C14 C13 C17 121.64(12) . . ? C12 C13 C17 119.76(12) . . ? C13 C14 C15 121.81(12) . . ? C13 C14 H14A 119.1 . . ? C15 C14 H14A 119.1 . . ? C16 C15 C14 118.78(12) . . ? C16 C15 C18 120.84(12) . . ? C14 C15 C18 120.38(12) . . ? C15 C16 C11 120.59(12) . . ? C15 C16 H16A 119.7 . . ? C11 C16 H16A 119.7 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C18 H18D 110.2 . . ? H18A C18 H18D 139.8 . . ? H18B C18 H18D 62.1 . . ? H18C C18 H18D 50.1 . . ? C15 C18 H18E 106.3 . . ? H18A C18 H18E 58.4 . . ? H18B C18 H18E 55.4 . . ? H18C C18 H18E 144.2 . . ? H18D C18 H18E 114.7 . . ? C15 C18 H18F 101.9 . . ? H18A C18 H18F 58.3 . . ? H18B C18 H18F 148.6 . . ? H18C C18 H18F 57.7 . . ? H18D C18 H18F 106.9 . . ? H18E C18 H18F 116.0 . . ? O1 S1 C21 105.41(6) . . ? O1 S1 C20 105.69(7) . . ? C21 S1 C20 98.65(8) . . ? S1 C20 H20A 109.5 . . ? S1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? S1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? S1 C21 H21A 109.5 . . ? S1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? S1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 S2 C31 106.62(7) . . ? O2 S2 C30 106.01(7) . . ? C31 S2 C30 96.86(8) . . ? S2 C30 H30A 109.5 . . ? S2 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? S2 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? S2 C31 H31A 109.5 . . ? S2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? S2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.895(17) 2.243(17) 3.0742(17) 154.4(15) . N4 H4 O1 0.880(16) 1.999(16) 2.8553(19) 164.0(15) . N5 H5 O2 0.861(16) 2.130(16) 2.9486(17) 158.7(14) . _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 34.89 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.730 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.082 data_dma44a _database_code_depnum_ccdc_archive 'CCDC 843773' #TrackingRef '7137_web_deposit_cif_file_4_DavidMcMorran_1315712607.dma44a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H46 N10 Ni, 2(C2 H3 N), 2(Cl O4)' _chemical_formula_sum 'C40 H52 Cl2 N12 Ni1 O8' _chemical_formula_weight 958.54 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.059(5) _cell_length_b 8.919(5) _cell_length_c 16.632(5) _cell_angle_alpha 101.045(5) _cell_angle_beta 101.543(5) _cell_angle_gamma 98.542(5) _cell_volume 1127.7(10) _cell_formula_units_Z 1 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 5992 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.62 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 0.613 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 0.901 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 38990 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.24 _reflns_number_total 4999 _reflns_number_gt 4258 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0479P)^2^+0.5618P] 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 4999 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.0000 0.0000 0.0000 0.01432(10) Uani 1 2 d S . . N1 N -0.12766(19) 0.07659(18) -0.08347(10) 0.0176(3) Uani 1 1 d . . . H1A H -0.095(3) 0.080(2) -0.1242(13) 0.017(5) Uiso 1 1 d . . . C1 C -0.2706(2) 0.1272(2) -0.08570(11) 0.0171(3) Uani 1 1 d . A . N2 N -0.3412(2) 0.14548(19) -0.01703(9) 0.0213(3) Uani 1 1 d . . . H2A H -0.425(3) 0.177(3) -0.0208(14) 0.029(6) Uiso 1 1 d . . . C2 C -0.2586(2) 0.1427(2) 0.06301(11) 0.0221(4) Uani 1 1 d . . . N3 N -0.11571(19) 0.09153(18) 0.07664(10) 0.0189(3) Uani 1 1 d . . . H3A H -0.081(3) 0.096(3) 0.1254(15) 0.030(6) Uiso 1 1 d . . . N4 N -0.3626(2) 0.1681(2) -0.15253(10) 0.0224(3) Uani 1 1 d . . . H4A H -0.426(3) 0.222(3) -0.1443(15) 0.031(7) Uiso 1 1 d . . . C3A C -0.3423(8) 0.1532(5) -0.23082(19) 0.0206(14) Uani 0.488(7) 1 d PG A 1 C4A C -0.3314(8) 0.0087(5) -0.2765(3) 0.0211(13) Uani 0.488(7) 1 d PG A 1 H4AA H -0.3331 -0.0760 -0.2515 0.025 Uiso 0.488(7) 1 calc PR A 1 C5A C -0.3179(6) -0.0092(5) -0.3597(2) 0.0231(11) Uani 0.488(7) 1 d PG A 1 C6A C -0.3153(5) 0.1174(7) -0.39718(18) 0.0246(14) Uani 0.488(7) 1 d PG A 1 H6AA H -0.3063 0.1055 -0.4528 0.030 Uiso 0.488(7) 1 calc PR A 1 C7A C -0.3262(5) 0.2620(6) -0.3515(2) 0.0223(11) Uani 0.488(7) 1 d PG A 1 C8A C -0.3397(6) 0.2798(5) -0.2683(2) 0.0195(11) Uani 0.488(7) 1 d PG A 1 H8AA H -0.3470 0.3765 -0.2377 0.023 Uiso 0.488(7) 1 calc PR A 1 C9A C -0.3107(7) -0.1679(7) -0.4096(3) 0.0328(13) Uani 0.488(7) 1 d P A 1 H9AA H -0.3058 -0.2397 -0.3733 0.049 Uiso 0.488(7) 1 calc PR A 1 H9AB H -0.2098 -0.1606 -0.4321 0.049 Uiso 0.488(7) 1 calc PR A 1 H9AC H -0.4120 -0.2041 -0.4549 0.049 Uiso 0.488(7) 1 calc PR A 1 C10A C -0.3189(6) 0.4032(6) -0.3896(3) 0.0324(13) Uani 0.488(7) 1 d P A 1 H10A H -0.3286 0.4918 -0.3490 0.049 Uiso 0.488(7) 1 calc PR A 1 H10B H -0.4125 0.3837 -0.4385 0.049 Uiso 0.488(7) 1 calc PR A 1 H10C H -0.2111 0.4237 -0.4055 0.049 Uiso 0.488(7) 1 calc PR A 1 C3B C -0.3386(8) 0.1182(5) -0.23986(18) 0.0168(12) Uani 0.512(7) 1 d PG A 2 C4B C -0.3116(8) -0.0300(5) -0.2711(2) 0.0206(12) Uani 0.512(7) 1 d PG A 2 H4BA H -0.3019 -0.1002 -0.2364 0.025 Uiso 0.512(7) 1 calc PR A 2 C5B C -0.2991(6) -0.0734(5) -0.3542(2) 0.0276(12) Uani 0.512(7) 1 d PG A 2 C6B C -0.3136(4) 0.0313(7) -0.40604(17) 0.0336(13) Uani 0.512(7) 1 d PG A 2 H6BA H -0.3052 0.0023 -0.4616 0.040 Uiso 0.512(7) 1 calc PR A 2 C7B C -0.3406(5) 0.1796(7) -0.3748(2) 0.0247(13) Uani 0.512(7) 1 d PG A 2 C8B C -0.3531(6) 0.2230(5) -0.2917(2) 0.0213(11) Uani 0.512(7) 1 d PG A 2 H8BA H -0.3711 0.3221 -0.2708 0.026 Uiso 0.512(7) 1 calc PR A 2 C9B C -0.2690(8) -0.2352(7) -0.3879(3) 0.0463(15) Uani 0.512(7) 1 d P A 2 H9BA H -0.2413 -0.2401 -0.4417 0.069 Uiso 0.512(7) 1 calc PR A 2 H9BB H -0.3716 -0.3106 -0.3940 0.069 Uiso 0.512(7) 1 calc PR A 2 H9BC H -0.1750 -0.2571 -0.3493 0.069 Uiso 0.512(7) 1 calc PR A 2 C10B C -0.3544(7) 0.2959(7) -0.4300(3) 0.0405(15) Uani 0.512(7) 1 d P A 2 H10D H -0.3580 0.2453 -0.4869 0.061 Uiso 0.512(7) 1 calc PR A 2 H10E H -0.2560 0.3797 -0.4096 0.061 Uiso 0.512(7) 1 calc PR A 2 H10F H -0.4579 0.3364 -0.4285 0.061 Uiso 0.512(7) 1 calc PR A 2 N5 N -0.3416(2) 0.1935(3) 0.12262(11) 0.0393(5) Uani 1 1 d . . . H5A H -0.401(3) 0.250(3) 0.1106(16) 0.036(7) Uiso 1 1 d . . . C11 C -0.2784(2) 0.2077(3) 0.21072(12) 0.0337(5) Uani 1 1 d . . . C12 C -0.2620(3) 0.3511(3) 0.26451(13) 0.0349(5) Uani 1 1 d . . . H12A H -0.2855 0.4365 0.2429 0.042 Uiso 1 1 calc R . . C13 C -0.2100(3) 0.3665(3) 0.35103(13) 0.0374(5) Uani 1 1 d . . . C14 C -0.1754(3) 0.2373(3) 0.38116(13) 0.0412(6) Uani 1 1 d . . . H14A H -0.1401 0.2477 0.4390 0.049 Uiso 1 1 calc R . . C15 C -0.1915(3) 0.0929(3) 0.32805(13) 0.0383(6) Uani 1 1 d . . . C16 C -0.2439(3) 0.0792(3) 0.24133(12) 0.0331(5) Uani 1 1 d . . . H16A H -0.2555 -0.0161 0.2042 0.040 Uiso 1 1 calc R . . C17 C -0.1938(3) 0.5235(3) 0.40926(14) 0.0493(7) Uani 1 1 d . . . H17A H -0.1744 0.5127 0.4665 0.074 Uiso 1 1 calc R . . H17B H -0.2982 0.5623 0.3952 0.074 Uiso 1 1 calc R . . H17C H -0.0984 0.5951 0.4030 0.074 Uiso 1 1 calc R . . C18 C -0.1609(4) -0.0480(3) 0.36173(15) 0.0542(8) Uani 1 1 d . . . H18A H -0.0848 -0.0155 0.4169 0.081 Uiso 1 1 calc R . . H18B H -0.1094 -0.1128 0.3248 0.081 Uiso 1 1 calc R . . H18C H -0.2689 -0.1056 0.3650 0.081 Uiso 1 1 calc R . . Cl1 Cl -0.71681(6) 0.35727(5) -0.10119(4) 0.03295(14) Uani 1 1 d . . . O1A O -0.5781(5) 0.4071(6) -0.1277(4) 0.0314(13) Uani 0.491(9) 1 d P B 1 O4A O -0.7449(5) 0.4789(5) -0.0307(3) 0.0314(14) Uani 0.491(9) 1 d P B 1 O1B O -0.6130(5) 0.3540(5) -0.1734(4) 0.0289(10) Uani 0.509(9) 1 d P B 2 O4B O -0.7015(4) 0.5196(4) -0.0689(3) 0.0292(12) Uani 0.509(9) 1 d P B 2 O2 O -0.66333(19) 0.2509(2) -0.05089(9) 0.0390(4) Uani 1 1 d . B . O3 O -0.88240(18) 0.29278(17) -0.15460(9) 0.0340(3) Uani 1 1 d . B . N20 N -0.6666(3) 0.2993(2) 0.15794(16) 0.0574(7) Uani 1 1 d . . . C20A C -0.7668(3) 0.3627(2) 0.13424(14) 0.0299(5) Uani 0.523(16) 1 d P C 1 C21A C -0.9048(6) 0.4583(7) 0.1231(8) 0.040(2) Uani 0.523(16) 1 d P C 1 H21A H -0.9610 0.4618 0.1689 0.060 Uiso 0.523(16) 1 calc PR C 1 H21B H -0.9879 0.4120 0.0708 0.060 Uiso 0.523(16) 1 calc PR C 1 H21C H -0.8535 0.5621 0.1223 0.060 Uiso 0.523(16) 1 calc PR C 1 C20B C -0.7668(3) 0.3627(2) 0.13424(14) 0.0299(5) Uani 0.477(16) 1 d P C 2 C21B C -0.8782(8) 0.4318(6) 0.0798(5) 0.0274(16) Uani 0.477(16) 1 d P C 2 H21D H -0.9429 0.3535 0.0312 0.041 Uiso 0.477(16) 1 calc PR C 2 H21E H -0.8100 0.5118 0.0624 0.041 Uiso 0.477(16) 1 calc PR C 2 H21F H -0.9562 0.4764 0.1095 0.041 Uiso 0.477(16) 1 calc PR C 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 Ni1 0.01358(16) 0.01685(17) 0.01305(16) 0.00296(12) 0.00349(12) 0.00468(12) N1 0.0201(8) 0.0217(8) 0.0137(7) 0.0053(6) 0.0075(6) 0.0062(6) C1 0.0172(8) 0.0142(8) 0.0179(8) 0.0022(7) 0.0020(7) 0.0013(6) N2 0.0161(8) 0.0300(9) 0.0172(7) 0.0008(6) 0.0025(6) 0.0111(7) C2 0.0175(9) 0.0297(10) 0.0168(8) -0.0009(7) 0.0039(7) 0.0055(7) N3 0.0164(7) 0.0269(8) 0.0125(7) 0.0025(6) 0.0020(6) 0.0059(6) N4 0.0212(8) 0.0272(9) 0.0217(8) 0.0097(7) 0.0038(6) 0.0104(7) C3A 0.009(2) 0.020(2) 0.027(3) 0.0010(19) -0.005(2) 0.0013(18) C4A 0.020(2) 0.022(3) 0.024(2) 0.013(2) 0.0025(18) 0.010(2) C5A 0.026(2) 0.019(3) 0.020(2) 0.000(2) -0.0008(18) 0.007(2) C6A 0.032(3) 0.028(4) 0.009(2) -0.004(2) 0.0045(17) 0.001(2) C7A 0.023(2) 0.024(3) 0.016(2) 0.004(2) -0.0004(17) 0.002(2) C8A 0.026(2) 0.015(3) 0.016(2) 0.0023(19) 0.0023(19) 0.002(2) C9A 0.043(3) 0.029(3) 0.025(2) 0.000(2) 0.008(2) 0.011(2) C10A 0.047(3) 0.029(3) 0.023(2) 0.013(2) 0.0092(19) 0.004(2) C3B 0.023(3) 0.024(3) 0.009(2) 0.0079(18) 0.0077(18) 0.009(2) C4B 0.021(2) 0.021(2) 0.017(2) 0.0032(17) -0.0022(17) 0.006(2) C5B 0.027(2) 0.027(3) 0.024(2) -0.002(2) 0.0015(17) 0.009(2) C6B 0.038(2) 0.043(4) 0.017(2) 0.002(3) 0.0029(18) 0.010(3) C7B 0.029(2) 0.037(4) 0.009(2) 0.006(2) 0.0071(18) 0.005(3) C8B 0.020(2) 0.021(3) 0.022(3) 0.005(2) 0.0040(19) 0.005(2) C9B 0.071(4) 0.035(3) 0.027(2) -0.008(2) 0.002(2) 0.023(3) C10B 0.052(3) 0.049(4) 0.030(2) 0.019(3) 0.016(2) 0.019(2) N5 0.0229(9) 0.0775(16) 0.0168(8) -0.0019(9) 0.0028(7) 0.0269(10) C11 0.0153(9) 0.0657(16) 0.0160(9) -0.0035(9) 0.0065(7) 0.0082(9) C12 0.0215(10) 0.0577(15) 0.0236(10) -0.0004(10) 0.0081(8) 0.0099(9) C13 0.0298(11) 0.0540(15) 0.0207(10) -0.0050(10) 0.0104(9) -0.0041(10) C14 0.0432(13) 0.0541(15) 0.0161(9) 0.0001(10) 0.0093(9) -0.0153(11) C15 0.0348(12) 0.0501(14) 0.0214(10) 0.0002(9) 0.0118(9) -0.0157(10) C16 0.0211(10) 0.0517(14) 0.0188(9) -0.0045(9) 0.0080(8) -0.0052(9) C17 0.0511(15) 0.0616(17) 0.0241(11) -0.0093(11) 0.0084(11) 0.0023(12) C18 0.0773(19) 0.0485(15) 0.0260(12) 0.0045(11) 0.0163(12) -0.0221(13) Cl1 0.0178(2) 0.0192(2) 0.0573(3) -0.0006(2) 0.0055(2) 0.00608(18) O1A 0.0208(17) 0.035(2) 0.051(3) 0.028(2) 0.0173(19) 0.0094(15) O4A 0.0342(19) 0.0279(19) 0.033(2) 0.0017(16) 0.0065(16) 0.0172(15) O1B 0.0318(19) 0.029(2) 0.035(2) 0.0126(18) 0.0191(18) 0.0121(15) O4B 0.0325(17) 0.0163(15) 0.038(2) 0.0002(14) 0.0097(15) 0.0067(12) O2 0.0297(8) 0.0616(11) 0.0327(8) 0.0128(7) 0.0091(7) 0.0257(7) O3 0.0293(8) 0.0330(8) 0.0340(8) 0.0075(6) -0.0021(6) 0.0016(6) N20 0.0380(12) 0.0375(12) 0.0799(17) -0.0017(11) -0.0168(11) 0.0165(10) C20A 0.0210(10) 0.0300(11) 0.0395(11) 0.0118(9) 0.0055(9) 0.0044(8) C21A 0.024(2) 0.029(3) 0.066(6) 0.012(3) 0.002(3) 0.0119(19) C20B 0.0210(10) 0.0300(11) 0.0395(11) 0.0118(9) 0.0055(9) 0.0044(8) C21B 0.031(3) 0.023(2) 0.028(3) 0.003(2) 0.006(2) 0.0100(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.8582(16) 2 ? Ni1 N1 1.8582(16) . ? Ni1 N3 1.8612(16) 2 ? Ni1 N3 1.8612(16) . ? N1 C1 1.295(2) . ? N1 H1A 0.78(2) . ? C1 N4 1.350(2) . ? C1 N2 1.368(2) . ? N2 C2 1.371(2) . ? N2 H2A 0.76(2) . ? C2 N3 1.295(2) . ? C2 N5 1.349(3) . ? N3 H3A 0.79(2) . ? N4 C3A 1.329(3) . ? N4 C3B 1.495(3) . ? N4 H4A 0.76(3) . ? C3A C4A 1.3900 . ? C3A C8A 1.3900 . ? C4A C5A 1.3900 . ? C4A H4AA 0.9300 . ? C5A C6A 1.3900 . ? C5A C9A 1.513(5) . ? C6A C7A 1.3900 . ? C6A H6AA 0.9300 . ? C7A C8A 1.3900 . ? C7A C10A 1.514(5) . ? C8A H8AA 0.9300 . ? C9A H9AA 0.9600 . ? C9A H9AB 0.9600 . ? C9A H9AC 0.9600 . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C3B C4B 1.3900 . ? C3B C8B 1.3900 . ? C4B C5B 1.3900 . ? C4B H4BA 0.9300 . ? C5B C6B 1.3900 . ? C5B C9B 1.517(6) . ? C6B C7B 1.3900 . ? C6B H6BA 0.9300 . ? C7B C8B 1.3900 . ? C7B C10B 1.513(5) . ? C8B H8BA 0.9300 . ? C9B H9BA 0.9600 . ? C9B H9BB 0.9600 . ? C9B H9BC 0.9600 . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? N5 C11 1.426(3) . ? N5 H5A 0.77(3) . ? C11 C16 1.382(3) . ? C11 C12 1.385(3) . ? C12 C13 1.390(3) . ? C12 H12A 0.9300 . ? C13 C14 1.385(4) . ? C13 C17 1.514(3) . ? C14 C15 1.388(3) . ? C14 H14A 0.9300 . ? C15 C16 1.395(3) . ? C15 C18 1.503(4) . ? C16 H16A 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? Cl1 O1A 1.329(3) . ? Cl1 O3 1.4150(16) . ? Cl1 O4B 1.422(3) . ? Cl1 O2 1.4374(17) . ? Cl1 O4A 1.515(4) . ? Cl1 O1B 1.594(4) . ? N20 C20A 1.105(3) . ? C20A C21A 1.502(6) . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? 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 N1 180.00(12) 2 . ? N1 Ni1 N3 89.66(7) 2 2 ? N1 Ni1 N3 90.34(7) . 2 ? N1 Ni1 N3 90.34(7) 2 . ? N1 Ni1 N3 89.66(7) . . ? N3 Ni1 N3 180.00(9) 2 . ? C1 N1 Ni1 129.45(13) . . ? C1 N1 H1A 111.5(15) . . ? Ni1 N1 H1A 119.0(15) . . ? N1 C1 N4 125.24(17) . . ? N1 C1 N2 121.06(16) . . ? N4 C1 N2 113.69(16) . . ? C1 N2 C2 125.27(16) . . ? C1 N2 H2A 117.5(18) . . ? C2 N2 H2A 115.8(18) . . ? N3 C2 N5 125.19(17) . . ? N3 C2 N2 120.83(17) . . ? N5 C2 N2 113.96(17) . . ? C2 N3 Ni1 129.58(13) . . ? C2 N3 H3A 111.1(17) . . ? Ni1 N3 H3A 119.1(17) . . ? C3A N4 C1 130.3(3) . . ? C3A N4 C3B 11.5(3) . . ? C1 N4 C3B 122.5(3) . . ? C3A N4 H4A 110.9(18) . . ? C1 N4 H4A 117.7(18) . . ? C3B N4 H4A 119.7(18) . . ? N4 C3A C4A 119.7(3) . . ? N4 C3A C8A 120.2(3) . . ? C4A C3A C8A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A H4AA 120.0 . . ? C5A C4A H4AA 120.0 . . ? C6A C5A C4A 120.0 . . ? C6A C5A C9A 120.4(3) . . ? C4A C5A C9A 119.5(3) . . ? C5A C6A C7A 120.0 . . ? C5A C6A H6AA 120.0 . . ? C7A C6A H6AA 120.0 . . ? C6A C7A C8A 120.0 . . ? C6A C7A C10A 121.3(3) . . ? C8A C7A C10A 118.6(3) . . ? C7A C8A C3A 120.0 . . ? C7A C8A H8AA 120.0 . . ? C3A C8A H8AA 120.0 . . ? C5A C9A H9AA 109.5 . . ? C5A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? C5A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? C7A C10A H10A 109.5 . . ? C7A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C7A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C4B C3B C8B 120.0 . . ? C4B C3B N4 122.2(3) . . ? C8B C3B N4 117.7(3) . . ? C5B C4B C3B 120.0 . . ? C5B C4B H4BA 120.0 . . ? C3B C4B H4BA 120.0 . . ? C4B C5B C6B 120.0 . . ? C4B C5B C9B 119.8(3) . . ? C6B C5B C9B 120.2(3) . . ? C7B C6B C5B 120.0 . . ? C7B C6B H6BA 120.0 . . ? C5B C6B H6BA 120.0 . . ? C6B C7B C8B 120.0 . . ? C6B C7B C10B 120.7(3) . . ? C8B C7B C10B 119.3(3) . . ? C7B C8B C3B 120.0 . . ? C7B C8B H8BA 120.0 . . ? C3B C8B H8BA 120.0 . . ? C5B C9B H9BA 109.5 . . ? C5B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? C5B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? C7B C10B H10D 109.5 . . ? C7B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C7B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C2 N5 C11 124.55(18) . . ? C2 N5 H5A 113.9(19) . . ? C11 N5 H5A 115.8(19) . . ? C16 C11 C12 121.3(2) . . ? C16 C11 N5 120.5(2) . . ? C12 C11 N5 118.1(2) . . ? C11 C12 C13 119.5(2) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? C14 C13 C12 118.8(2) . . ? C14 C13 C17 122.1(2) . . ? C12 C13 C17 119.0(2) . . ? C13 C14 C15 122.3(2) . . ? C13 C14 H14A 118.8 . . ? C15 C14 H14A 118.8 . . ? C14 C15 C16 118.2(2) . . ? C14 C15 C18 121.8(2) . . ? C16 C15 C18 120.0(2) . . ? C11 C16 C15 119.9(2) . . ? C11 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1A Cl1 O3 124.5(3) . . ? O1A Cl1 O4B 82.0(2) . . ? O3 Cl1 O4B 110.54(14) . . ? O1A Cl1 O2 104.56(17) . . ? O3 Cl1 O2 109.93(10) . . ? O4B Cl1 O2 124.1(2) . . ? O1A Cl1 O4A 111.7(2) . . ? O3 Cl1 O4A 105.74(15) . . ? O4B Cl1 O4A 35.24(15) . . ? O2 Cl1 O4A 97.1(2) . . ? O1A Cl1 O1B 29.5(2) . . ? O3 Cl1 O1B 97.0(2) . . ? O4B Cl1 O1B 102.4(2) . . ? O2 Cl1 O1B 109.02(14) . . ? O4A Cl1 O1B 136.8(2) . . ? N20 C20A C21A 166.7(6) . . ? H21D C21B H21E 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? 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 N1 C1 20(100) 2 . . . ? N3 Ni1 N1 C1 162.14(17) 2 . . . ? N3 Ni1 N1 C1 -17.86(17) . . . . ? Ni1 N1 C1 N4 -173.77(13) . . . . ? Ni1 N1 C1 N2 7.0(3) . . . . ? N1 C1 N2 C2 13.1(3) . . . . ? N4 C1 N2 C2 -166.26(18) . . . . ? C1 N2 C2 N3 -13.9(3) . . . . ? C1 N2 C2 N5 167.57(19) . . . . ? N5 C2 N3 Ni1 173.05(17) . . . . ? N2 C2 N3 Ni1 -5.3(3) . . . . ? N1 Ni1 N3 C2 -162.97(18) 2 . . . ? N1 Ni1 N3 C2 17.03(18) . . . . ? N3 Ni1 N3 C2 -136(52) 2 . . . ? N1 C1 N4 C3A 7.4(4) . . . . ? N2 C1 N4 C3A -173.3(3) . . . . ? N1 C1 N4 C3B 17.9(4) . . . . ? N2 C1 N4 C3B -162.8(3) . . . . ? C1 N4 C3A C4A 52.8(5) . . . . ? C3B N4 C3A C4A 2(2) . . . . ? C1 N4 C3A C8A -130.1(3) . . . . ? C3B N4 C3A C8A 179(3) . . . . ? N4 C3A C4A C5A 177.1(5) . . . . ? C8A C3A C4A C5A 0.0 . . . . ? C3A C4A C5A C6A 0.0 . . . . ? C3A C4A C5A C9A -178.4(4) . . . . ? C4A C5A C6A C7A 0.0 . . . . ? C9A C5A C6A C7A 178.4(4) . . . . ? C5A C6A C7A C8A 0.0 . . . . ? C5A C6A C7A C10A 178.3(4) . . . . ? C6A C7A C8A C3A 0.0 . . . . ? C10A C7A C8A C3A -178.4(4) . . . . ? N4 C3A C8A C7A -177.1(5) . . . . ? C4A C3A C8A C7A 0.0 . . . . ? C3A N4 C3B C4B 175(3) . . . . ? C1 N4 C3B C4B 39.5(4) . . . . ? C3A N4 C3B C8B -8(2) . . . . ? C1 N4 C3B C8B -143.8(3) . . . . ? C8B C3B C4B C5B 0.0 . . . . ? N4 C3B C4B C5B 176.6(5) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C3B C4B C5B C9B 179.8(4) . . . . ? C4B C5B C6B C7B 0.0 . . . . ? C9B C5B C6B C7B -179.8(4) . . . . ? C5B C6B C7B C8B 0.0 . . . . ? C5B C6B C7B C10B 179.2(4) . . . . ? C6B C7B C8B C3B 0.0 . . . . ? C10B C7B C8B C3B -179.2(4) . . . . ? C4B C3B C8B C7B 0.0 . . . . ? N4 C3B C8B C7B -176.8(5) . . . . ? N3 C2 N5 C11 4.2(4) . . . . ? N2 C2 N5 C11 -177.3(2) . . . . ? C2 N5 C11 C16 -58.9(3) . . . . ? C2 N5 C11 C12 124.6(2) . . . . ? C16 C11 C12 C13 -0.1(3) . . . . ? N5 C11 C12 C13 176.39(18) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C11 C12 C13 C17 -179.6(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C17 C13 C14 C15 179.5(2) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C13 C14 C15 C18 -177.3(2) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? N5 C11 C16 C15 -176.35(18) . . . . ? C14 C15 C16 C11 -0.1(3) . . . . ? C18 C15 C16 C11 177.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.78(2) 2.56(2) 3.115(2) 129.8(18) 1_655 N2 H2A O2 0.76(2) 2.12(3) 2.878(3) 171(2) . N4 H4A O1B 0.76(3) 2.09(3) 2.806(4) 157(2) . N5 H5A O4B 0.77(3) 2.37(3) 2.864(6) 122(2) 2_465 N5 H5A N20 0.77(3) 2.49(3) 3.038(3) 129(2) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.24 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.565 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.059 data_dma51 _database_code_depnum_ccdc_archive 'CCDC 843774' #TrackingRef '7138_web_deposit_cif_file_5_DavidMcMorran_1315712607.dma51.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 Br2 N5' _chemical_formula_sum 'C14 H13 Br2 N5' _chemical_formula_weight 411.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.351(5) _cell_length_b 8.876(5) _cell_length_c 26.832(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 1512.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 7592 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 24.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_max 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 5.360 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.694 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 26016 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.51 _reflns_number_total 2639 _reflns_number_gt 2288 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0319P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(11) _refine_ls_number_reflns 2639 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0610 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _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 N1 N 0.5891(6) -0.1320(4) 0.27024(13) 0.0168(8) Uani 1 1 d . . . H1A H 0.663(6) -0.114(5) 0.2970(16) 0.025 Uiso 1 1 d . . . H1B H 0.510(7) -0.201(5) 0.2703(15) 0.025 Uiso 1 1 d . . . C1 C 0.5757(6) -0.0221(4) 0.23677(13) 0.0122(9) Uani 1 1 d . . . N2 N 0.6965(5) 0.0991(3) 0.23432(10) 0.0116(7) Uani 1 1 d . . . C2 C 0.8458(5) 0.1275(4) 0.27039(14) 0.0135(9) Uani 1 1 d . . . N3 N 0.9394(5) 0.2674(4) 0.26198(13) 0.0155(9) Uani 1 1 d . . . H3A H 0.938(7) 0.291(5) 0.2316(15) 0.023 Uiso 1 1 d . . . H3B H 1.048(7) 0.288(5) 0.2765(14) 0.023 Uiso 1 1 d . . . N4 N 0.4220(5) -0.0398(4) 0.20134(12) 0.0151(9) Uani 1 1 d . . . H4B H 0.321(7) -0.082(5) 0.2088(15) 0.023 Uiso 1 1 d . . . C3 C 0.3776(6) 0.0632(4) 0.16180(13) 0.0118(9) Uani 1 1 d . . . C4 C 0.1692(6) 0.1041(5) 0.15352(14) 0.0181(10) Uani 1 1 d . . . H4 H 0.0632 0.0658 0.1738 0.022 Uiso 1 1 calc R . . C5 C 0.1196(6) 0.2016(5) 0.11511(13) 0.0180(9) Uani 1 1 d . . . H5 H -0.0194 0.2301 0.1096 0.022 Uiso 1 1 calc R . . C6 C 0.2785(7) 0.2564(4) 0.08488(13) 0.0186(10) Uani 1 1 d . . . C7 C 0.4862(7) 0.2155(4) 0.09266(12) 0.0174(9) Uani 1 1 d . . . H7 H 0.5924 0.2538 0.0725 0.021 Uiso 1 1 calc R . . C8 C 0.5335(6) 0.1167(5) 0.13091(12) 0.0146(9) Uani 1 1 d . . . H8 H 0.6720 0.0861 0.1358 0.018 Uiso 1 1 calc R . . Br1 Br 0.20916(7) 0.39557(5) 0.033485(16) 0.02729(14) Uani 1 1 d . . . N5 N 0.8880(5) 0.0449(4) 0.30903(11) 0.0147(8) Uani 1 1 d . . . C9 C 1.0325(6) 0.1051(4) 0.34428(12) 0.0132(9) Uani 1 1 d . . . C10 C 0.9764(6) 0.2226(4) 0.37593(12) 0.0143(9) Uani 1 1 d . . . H10 H 0.8409 0.2619 0.3742 0.017 Uiso 1 1 calc R . . C11 C 1.1154(6) 0.2815(5) 0.40954(13) 0.0158(9) Uani 1 1 d . . . H11 H 1.0751 0.3612 0.4299 0.019 Uiso 1 1 calc R . . C12 C 1.3160(6) 0.2226(4) 0.41317(12) 0.0146(9) Uani 1 1 d . . . C13 C 1.3778(6) 0.1051(5) 0.38278(13) 0.0163(9) Uani 1 1 d . . . H13 H 1.5133 0.0660 0.3850 0.020 Uiso 1 1 calc R . . C14 C 1.2352(6) 0.0460(4) 0.34884(14) 0.0180(10) Uani 1 1 d . . . H14 H 1.2754 -0.0344 0.3288 0.022 Uiso 1 1 calc R . . Br2 Br 1.50884(6) 0.30359(4) 0.460301(13) 0.02079(13) Uani 1 1 d . . . 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 N1 0.014(2) 0.012(2) 0.0240(19) 0.0028(17) -0.0028(16) -0.0032(16) C1 0.013(2) 0.009(2) 0.015(2) -0.0043(18) 0.0024(18) 0.0060(19) N2 0.0103(17) 0.0103(19) 0.0143(16) -0.0006(14) -0.0017(14) 0.0000(17) C2 0.012(2) 0.009(2) 0.020(2) 0.0001(18) 0.0063(18) -0.0011(19) N3 0.013(2) 0.016(2) 0.0174(18) -0.0005(16) -0.0040(16) -0.0048(16) N4 0.010(2) 0.014(2) 0.0208(18) 0.0003(15) 0.0033(16) -0.0062(16) C3 0.017(2) 0.006(2) 0.012(2) -0.0008(16) -0.0025(17) -0.0013(18) C4 0.015(3) 0.011(2) 0.027(2) 0.000(2) 0.0024(17) -0.007(2) C5 0.015(2) 0.016(2) 0.024(2) -0.001(2) -0.0070(18) 0.001(2) C6 0.027(3) 0.015(2) 0.0136(19) 0.0020(16) -0.010(2) 0.000(2) C7 0.021(2) 0.022(2) 0.0096(18) -0.0031(17) 0.0032(18) -0.005(2) C8 0.010(2) 0.019(2) 0.0148(19) 0.0003(18) 0.0007(17) -0.001(2) Br1 0.0339(3) 0.0226(3) 0.0253(2) 0.00855(19) -0.0092(2) -0.0022(2) N5 0.0122(18) 0.014(2) 0.0175(18) -0.0016(15) -0.0032(15) -0.0004(15) C9 0.017(2) 0.009(2) 0.0144(18) 0.0038(17) -0.0005(17) 0.003(2) C10 0.012(2) 0.019(2) 0.0122(19) 0.0046(17) 0.0032(17) -0.002(2) C11 0.018(2) 0.008(2) 0.021(2) -0.0033(17) 0.0072(18) 0.001(2) C12 0.017(2) 0.018(2) 0.0085(19) 0.0051(17) -0.0016(17) -0.002(2) C13 0.008(2) 0.019(3) 0.022(2) 0.0001(19) -0.0012(17) 0.003(2) C14 0.020(3) 0.015(2) 0.018(2) -0.0042(17) 0.0010(19) 0.004(2) Br2 0.0184(2) 0.0228(3) 0.0212(2) -0.00525(18) -0.00449(19) 0.0007(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C1 1.329(5) . ? N1 H1A 0.87(4) . ? N1 H1B 0.80(4) . ? C1 N2 1.322(5) . ? C1 N4 1.372(5) . ? N2 C2 1.378(5) . ? C2 N5 1.298(5) . ? C2 N3 1.395(5) . ? N3 H3A 0.84(4) . ? N3 H3B 0.81(4) . ? N4 C3 1.429(5) . ? N4 H4B 0.77(4) . ? C3 C8 1.376(5) . ? C3 C4 1.390(5) . ? C4 C5 1.382(6) . ? C4 H4 0.9300 . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 C7 1.384(6) . ? C6 Br1 1.903(4) . ? C7 C8 1.383(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? N5 C9 1.422(5) . ? C9 C10 1.391(5) . ? C9 C14 1.396(6) . ? C10 C11 1.366(5) . ? C10 H10 0.9300 . ? C11 C12 1.380(6) . ? C11 H11 0.9300 . ? C12 C13 1.381(5) . ? C12 Br2 1.902(4) . ? C13 C14 1.387(5) . ? C13 H13 0.9300 . ? C14 H14 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 C1 N1 H1A 117(3) . . ? C1 N1 H1B 122(3) . . ? H1A N1 H1B 119(4) . . ? N2 C1 N1 126.4(4) . . ? N2 C1 N4 118.1(3) . . ? N1 C1 N4 115.4(4) . . ? C1 N2 C2 120.8(3) . . ? N5 C2 N2 126.9(4) . . ? N5 C2 N3 123.0(4) . . ? N2 C2 N3 110.0(3) . . ? C2 N3 H3A 112(3) . . ? C2 N3 H3B 119(3) . . ? H3A N3 H3B 115(4) . . ? C1 N4 C3 125.6(3) . . ? C1 N4 H4B 118(3) . . ? C3 N4 H4B 110(3) . . ? C8 C3 C4 119.9(3) . . ? C8 C3 N4 121.7(4) . . ? C4 C3 N4 118.3(3) . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C7 121.0(3) . . ? C5 C6 Br1 119.0(3) . . ? C7 C6 Br1 120.0(3) . . ? C8 C7 C6 119.0(4) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C3 C8 C7 120.6(4) . . ? C3 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C2 N5 C9 116.9(3) . . ? C10 C9 C14 117.7(3) . . ? C10 C9 N5 121.5(3) . . ? C14 C9 N5 120.8(3) . . ? C11 C10 C9 121.6(4) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 120.5(4) . . ? C11 C12 Br2 119.9(3) . . ? C13 C12 Br2 119.7(3) . . ? C12 C13 C14 119.2(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C9 121.2(4) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? 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 C1 N2 C2 -4.6(6) . . . . ? N4 C1 N2 C2 176.4(3) . . . . ? C1 N2 C2 N5 0.6(6) . . . . ? C1 N2 C2 N3 -174.8(3) . . . . ? N2 C1 N4 C3 -1.0(5) . . . . ? N1 C1 N4 C3 179.9(3) . . . . ? C1 N4 C3 C8 50.5(5) . . . . ? C1 N4 C3 C4 -132.4(4) . . . . ? C8 C3 C4 C5 -1.8(6) . . . . ? N4 C3 C4 C5 -179.0(3) . . . . ? C3 C4 C5 C6 0.7(6) . . . . ? C4 C5 C6 C7 -0.3(6) . . . . ? C4 C5 C6 Br1 -178.0(3) . . . . ? C5 C6 C7 C8 0.9(6) . . . . ? Br1 C6 C7 C8 178.6(3) . . . . ? C4 C3 C8 C7 2.4(6) . . . . ? N4 C3 C8 C7 179.5(3) . . . . ? C6 C7 C8 C3 -1.9(6) . . . . ? N2 C2 N5 C9 -173.1(3) . . . . ? N3 C2 N5 C9 1.8(5) . . . . ? C2 N5 C9 C10 72.8(5) . . . . ? C2 N5 C9 C14 -108.4(4) . . . . ? C14 C9 C10 C11 1.7(5) . . . . ? N5 C9 C10 C11 -179.4(3) . . . . ? C9 C10 C11 C12 -1.1(6) . . . . ? C10 C11 C12 C13 0.5(6) . . . . ? C10 C11 C12 Br2 -179.5(3) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? Br2 C12 C13 C14 179.4(3) . . . . ? C12 C13 C14 C9 1.2(6) . . . . ? C10 C9 C14 C13 -1.8(6) . . . . ? N5 C9 C14 C13 179.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N5 0.87(4) 2.03(4) 2.674(5) 129(4) . N1 H1B N2 0.80(4) 2.21(5) 3.000(5) 176(4) 4_645 N4 H4B N3 0.77(4) 2.27(4) 3.027(5) 170(5) 4_645 _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.578 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.100 data_dma58a _database_code_depnum_ccdc_archive 'CCDC 843775' #TrackingRef '7139_web_deposit_cif_file_6_DavidMcMorran_1315712607.dma58a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H44 N10 Ni O8, 2(C12 H7 N O2)' _chemical_formula_sum 'C60 H58 N12 Ni O12' _chemical_formula_weight 1197.89 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3986(3) _cell_length_b 14.5430(8) _cell_length_c 14.5749(12) _cell_angle_alpha 116.861(4) _cell_angle_beta 96.539(4) _cell_angle_gamma 98.148(3) _cell_volume 1356.50(15) _cell_formula_units_Z 1 _cell_measurement_temperature 92(2) _cell_measurement_reflns_used 8041 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 626 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7859 _exptl_absorpt_correction_T_max 0.9178 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 92(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 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 40825 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.64 _reflns_number_total 5095 _reflns_number_gt 4257 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution SAINT _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0277P)^2^+1.4022P] 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 5095 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.5000 0.5000 0.0000 0.01405(11) Uani 1 2 d S . . N1 N 0.5280(2) 0.62881(13) 0.11855(14) 0.0159(4) Uani 1 1 d . . . H1 H 0.477(3) 0.6310(18) 0.1665(19) 0.023(6) Uiso 1 1 d . . . C1 C 0.6274(3) 0.72207(15) 0.14364(15) 0.0140(4) Uani 1 1 d . . . N2 N 0.2711(2) 0.25446(12) -0.08251(13) 0.0148(4) Uani 1 1 d . . . C2 C 0.2646(3) 0.33318(15) 0.01247(15) 0.0143(4) Uani 1 1 d . . . N3 N 0.3455(2) 0.43358(13) 0.05253(14) 0.0166(4) Uani 1 1 d . . . H3 H 0.328(3) 0.4681(18) 0.1139(19) 0.020(6) Uiso 1 1 d . . . N4 N 0.6382(2) 0.80759(13) 0.24024(13) 0.0168(4) Uani 1 1 d . . . H4 H 0.670(3) 0.8676(19) 0.2426(18) 0.022(6) Uiso 1 1 d . . . C3 C 0.5315(3) 0.80675(15) 0.31473(15) 0.0166(4) Uani 1 1 d . . . C4 C 0.4210(3) 0.88095(15) 0.35019(15) 0.0175(4) Uani 1 1 d . . . H4A H 0.4169 0.9292 0.3250 0.021 Uiso 1 1 calc R . . C5 C 0.3168(3) 0.88138(16) 0.42404(16) 0.0191(4) Uani 1 1 d . . . C6 C 0.3234(3) 0.81042(16) 0.46266(16) 0.0203(5) Uani 1 1 d . . . H6A H 0.2539 0.8117 0.5123 0.024 Uiso 1 1 calc R . . C7 C 0.4349(3) 0.73743(16) 0.42650(16) 0.0179(4) Uani 1 1 d . . . C8 C 0.5411(3) 0.73528(15) 0.35312(15) 0.0175(4) Uani 1 1 d . . . H8A H 0.6172 0.6870 0.3301 0.021 Uiso 1 1 calc R . . O1 O 0.1966(2) 0.94657(12) 0.46043(12) 0.0256(4) Uani 1 1 d . . . C9 C 0.1689(3) 1.01351(19) 0.4150(2) 0.0302(5) Uani 1 1 d . . . H9A H 0.0819 1.0551 0.4470 0.045 Uiso 1 1 calc R . . H9B H 0.1205 0.9711 0.3410 0.045 Uiso 1 1 calc R . . H9C H 0.2856 1.0594 0.4265 0.045 Uiso 1 1 calc R . . O2 O 0.4349(2) 0.67018(11) 0.46872(11) 0.0228(3) Uani 1 1 d . . . C10 C 0.4985(3) 0.57592(17) 0.41193(17) 0.0244(5) Uani 1 1 d . . . H10A H 0.4925 0.5352 0.4486 0.037 Uiso 1 1 calc R . . H10B H 0.6250 0.5938 0.4059 0.037 Uiso 1 1 calc R . . H10C H 0.4210 0.5352 0.3431 0.037 Uiso 1 1 calc R . . N5 N 0.1614(2) 0.29904(14) 0.06847(13) 0.0161(4) Uani 1 1 d . . . H5 H 0.148(3) 0.232(2) 0.0508(19) 0.029(7) Uiso 1 1 d . . . C11 C 0.1161(3) 0.36260(15) 0.16540(15) 0.0154(4) Uani 1 1 d . . . C12 C 0.0596(3) 0.45620(15) 0.18553(16) 0.0167(4) Uani 1 1 d . . . H12A H 0.0540 0.4794 0.1356 0.020 Uiso 1 1 calc R . . C13 C 0.0116(3) 0.51430(15) 0.28188(16) 0.0176(4) Uani 1 1 d . . . C14 C 0.0147(3) 0.47952(16) 0.35569(16) 0.0201(5) Uani 1 1 d . . . H14A H -0.0170 0.5192 0.4199 0.024 Uiso 1 1 calc R . . C15 C 0.0660(3) 0.38436(16) 0.33265(16) 0.0184(4) Uani 1 1 d . . . C16 C 0.1186(3) 0.32562(15) 0.23831(16) 0.0168(4) Uani 1 1 d . . . H16A H 0.1548 0.2626 0.2241 0.020 Uiso 1 1 calc R . . O3 O -0.0458(2) 0.60726(11) 0.30871(12) 0.0228(3) Uani 1 1 d . . . C17 C -0.0172(3) 0.65571(17) 0.24390(18) 0.0235(5) Uani 1 1 d . . . H17A H -0.0626 0.7197 0.2703 0.035 Uiso 1 1 calc R . . H17B H -0.0833 0.6083 0.1733 0.035 Uiso 1 1 calc R . . H17C H 0.1135 0.6717 0.2445 0.035 Uiso 1 1 calc R . . O4 O 0.0639(2) 0.35519(11) 0.40971(11) 0.0243(3) Uani 1 1 d . . . C18 C 0.1080(3) 0.25669(17) 0.38978(18) 0.0241(5) Uani 1 1 d . . . H18A H 0.1013 0.2464 0.4500 0.036 Uiso 1 1 calc R . . H18B H 0.2318 0.2565 0.3760 0.036 Uiso 1 1 calc R . . H18C H 0.0208 0.2007 0.3299 0.036 Uiso 1 1 calc R . . C20 C 0.3389(3) -0.13037(15) -0.18650(16) 0.0171(4) Uani 1 1 d . . . C21 C 0.3904(3) -0.20620(16) -0.27167(17) 0.0205(5) Uani 1 1 d . . . H21A H 0.4071 -0.1951 -0.3285 0.025 Uiso 1 1 calc R . . C22 C 0.4177(3) -0.29991(16) -0.27291(17) 0.0225(5) Uani 1 1 d . . . H22A H 0.4518 -0.3510 -0.3310 0.027 Uiso 1 1 calc R . . C23 C 0.3951(3) -0.31740(16) -0.19018(17) 0.0214(5) Uani 1 1 d . . . H23A H 0.4137 -0.3803 -0.1925 0.026 Uiso 1 1 calc R . . C24 C 0.3436(3) -0.24088(16) -0.10080(16) 0.0185(4) Uani 1 1 d . . . C25 C 0.3151(3) -0.25645(17) -0.01411(17) 0.0211(5) Uani 1 1 d . . . H25A H 0.3317 -0.3189 -0.0146 0.025 Uiso 1 1 calc R . . C26 C 0.2634(3) -0.18101(17) 0.07065(17) 0.0214(5) Uani 1 1 d . . . H26A H 0.2451 -0.1926 0.1270 0.026 Uiso 1 1 calc R . . C27 C 0.2380(3) -0.08632(16) 0.07270(16) 0.0198(4) Uani 1 1 d . . . H27A H 0.2046 -0.0350 0.1309 0.024 Uiso 1 1 calc R . . C28 C 0.2624(3) -0.06891(16) -0.01085(16) 0.0170(4) Uani 1 1 d . . . C29 C 0.3159(3) -0.14589(15) -0.09914(16) 0.0161(4) Uani 1 1 d . . . C30 C 0.3059(3) -0.03272(15) -0.18610(16) 0.0175(4) Uani 1 1 d . . . C31 C 0.2318(3) 0.02947(15) -0.00958(16) 0.0167(4) Uani 1 1 d . . . O5 O 0.1837(2) 0.09931(11) 0.06300(11) 0.0199(3) Uani 1 1 d . . . O6 O 0.3172(2) -0.01523(11) -0.25987(11) 0.0234(3) Uani 1 1 d . . . N6 N 0.2574(2) 0.04000(14) -0.09708(13) 0.0174(4) Uani 1 1 d . . . H6B H 0.244(3) 0.098(2) -0.0968(19) 0.028(7) Uiso 1 1 d . . . 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 0.0167(2) 0.01129(19) 0.01500(19) 0.00627(15) 0.00565(15) 0.00334(14) N1 0.0196(9) 0.0152(9) 0.0143(9) 0.0073(7) 0.0075(7) 0.0037(7) C1 0.0153(10) 0.0123(10) 0.0153(10) 0.0068(8) 0.0020(8) 0.0054(8) N2 0.0164(9) 0.0142(8) 0.0157(9) 0.0077(7) 0.0056(7) 0.0046(7) C2 0.0147(10) 0.0140(10) 0.0170(10) 0.0091(8) 0.0036(8) 0.0047(8) N3 0.0212(10) 0.0129(8) 0.0141(9) 0.0044(7) 0.0076(7) 0.0034(7) N4 0.0217(10) 0.0117(9) 0.0170(9) 0.0064(7) 0.0074(7) 0.0029(7) C3 0.0179(10) 0.0143(10) 0.0141(10) 0.0047(8) 0.0028(8) 0.0012(8) C4 0.0215(11) 0.0134(10) 0.0166(10) 0.0061(8) 0.0036(8) 0.0041(8) C5 0.0183(11) 0.0162(10) 0.0183(11) 0.0039(9) 0.0038(8) 0.0055(8) C6 0.0204(11) 0.0225(11) 0.0182(11) 0.0087(9) 0.0085(9) 0.0052(9) C7 0.0197(11) 0.0173(10) 0.0155(10) 0.0086(9) 0.0005(8) 0.0001(8) C8 0.0220(11) 0.0134(10) 0.0163(10) 0.0055(8) 0.0054(9) 0.0057(8) O1 0.0287(9) 0.0259(8) 0.0299(9) 0.0148(7) 0.0149(7) 0.0159(7) C9 0.0321(13) 0.0294(13) 0.0399(14) 0.0194(11) 0.0185(11) 0.0192(11) O2 0.0319(9) 0.0228(8) 0.0198(8) 0.0136(7) 0.0086(7) 0.0094(7) C10 0.0333(13) 0.0206(11) 0.0240(12) 0.0141(10) 0.0056(10) 0.0080(10) N5 0.0197(9) 0.0109(9) 0.0191(9) 0.0074(7) 0.0083(7) 0.0028(7) C11 0.0126(10) 0.0135(10) 0.0169(10) 0.0049(8) 0.0046(8) 0.0004(8) C12 0.0153(10) 0.0165(10) 0.0201(11) 0.0101(9) 0.0045(8) 0.0030(8) C13 0.0134(10) 0.0151(10) 0.0224(11) 0.0069(9) 0.0050(8) 0.0037(8) C14 0.0208(11) 0.0213(11) 0.0177(11) 0.0070(9) 0.0091(9) 0.0068(9) C15 0.0170(11) 0.0215(11) 0.0185(11) 0.0112(9) 0.0047(8) 0.0029(8) C16 0.0159(10) 0.0138(10) 0.0204(11) 0.0077(9) 0.0046(8) 0.0030(8) O3 0.0276(9) 0.0191(8) 0.0276(8) 0.0122(7) 0.0138(7) 0.0125(6) C17 0.0230(12) 0.0211(11) 0.0297(12) 0.0133(10) 0.0068(10) 0.0089(9) O4 0.0356(9) 0.0234(8) 0.0198(8) 0.0128(7) 0.0105(7) 0.0111(7) C18 0.0260(12) 0.0246(12) 0.0263(12) 0.0162(10) 0.0051(10) 0.0050(9) C20 0.0141(10) 0.0154(10) 0.0197(11) 0.0074(9) 0.0021(8) 0.0016(8) C21 0.0213(11) 0.0177(11) 0.0210(11) 0.0085(9) 0.0036(9) 0.0030(9) C22 0.0207(11) 0.0166(11) 0.0250(12) 0.0050(9) 0.0042(9) 0.0062(9) C23 0.0166(11) 0.0147(10) 0.0310(12) 0.0099(9) 0.0001(9) 0.0047(8) C24 0.0126(10) 0.0165(10) 0.0247(11) 0.0102(9) -0.0009(8) 0.0006(8) C25 0.0163(11) 0.0188(11) 0.0290(12) 0.0146(10) -0.0023(9) 0.0004(8) C26 0.0180(11) 0.0249(11) 0.0248(12) 0.0165(10) 0.0006(9) 0.0021(9) C27 0.0178(11) 0.0193(11) 0.0206(11) 0.0085(9) 0.0031(9) 0.0034(9) C28 0.0130(10) 0.0157(10) 0.0200(11) 0.0083(9) -0.0004(8) 0.0001(8) C29 0.0120(10) 0.0131(10) 0.0206(11) 0.0074(9) -0.0006(8) 0.0003(8) C30 0.0171(11) 0.0140(10) 0.0191(11) 0.0071(9) 0.0018(8) 0.0008(8) C31 0.0125(10) 0.0158(10) 0.0202(11) 0.0087(9) 0.0009(8) 0.0002(8) O5 0.0227(8) 0.0153(7) 0.0220(8) 0.0082(6) 0.0073(6) 0.0057(6) O6 0.0354(9) 0.0166(8) 0.0205(8) 0.0096(6) 0.0083(7) 0.0071(7) N6 0.0214(10) 0.0131(9) 0.0210(9) 0.0102(8) 0.0055(7) 0.0060(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N3 1.8388(17) 2_665 ? Ni1 N3 1.8388(17) . ? Ni1 N1 1.8497(17) 2_665 ? Ni1 N1 1.8497(17) . ? N1 C1 1.312(3) . ? N1 H1 0.82(2) . ? C1 N2 1.352(2) 2_665 ? C1 N4 1.378(2) . ? N2 C2 1.352(2) . ? N2 C1 1.352(2) 2_665 ? C2 N3 1.316(3) . ? C2 N5 1.377(2) . ? N3 H3 0.84(2) . ? N4 C3 1.416(3) . ? N4 H4 0.85(2) . ? C3 C8 1.391(3) . ? C3 C4 1.394(3) . ? C4 C5 1.392(3) . ? C4 H4A 0.9300 . ? C5 O1 1.365(2) . ? C5 C6 1.385(3) . ? C6 C7 1.388(3) . ? C6 H6A 0.9300 . ? C7 O2 1.371(2) . ? C7 C8 1.389(3) . ? C8 H8A 0.9300 . ? O1 C9 1.427(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? O2 C10 1.426(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N5 C11 1.406(3) . ? N5 H5 0.87(2) . ? C11 C16 1.391(3) . ? C11 C12 1.394(3) . ? C12 C13 1.392(3) . ? C12 H12A 0.9300 . ? C13 O3 1.373(2) . ? C13 C14 1.380(3) . ? C14 C15 1.389(3) . ? C14 H14A 0.9300 . ? C15 O4 1.369(2) . ? C15 C16 1.388(3) . ? C16 H16A 0.9300 . ? O3 C17 1.428(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O4 C18 1.422(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 C21 1.375(3) . ? C20 C29 1.414(3) . ? C20 C30 1.472(3) . ? C21 C22 1.398(3) . ? C21 H21A 0.9300 . ? C22 C23 1.363(3) . ? C22 H22A 0.9300 . ? C23 C24 1.416(3) . ? C23 H23A 0.9300 . ? C24 C25 1.413(3) . ? C24 C29 1.415(3) . ? C25 C26 1.370(3) . ? C25 H25A 0.9300 . ? C26 C27 1.404(3) . ? C26 H26A 0.9300 . ? C27 C28 1.377(3) . ? C27 H27A 0.9300 . ? C28 C29 1.416(3) . ? C28 C31 1.472(3) . ? C30 O6 1.220(2) . ? C30 N6 1.380(3) . ? C31 O5 1.223(2) . ? C31 N6 1.382(3) . ? N6 H6B 0.87(3) . ? 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 N3 Ni1 N3 180.0 2_665 . ? N3 Ni1 N1 91.32(8) 2_665 2_665 ? N3 Ni1 N1 88.68(8) . 2_665 ? N3 Ni1 N1 88.68(8) 2_665 . ? N3 Ni1 N1 91.32(8) . . ? N1 Ni1 N1 180.00(11) 2_665 . ? C1 N1 Ni1 130.24(15) . . ? C1 N1 H1 111.0(16) . . ? Ni1 N1 H1 118.6(16) . . ? N1 C1 N2 125.98(18) . 2_665 ? N1 C1 N4 120.79(18) . . ? N2 C1 N4 113.22(17) 2_665 . ? C2 N2 C1 118.56(16) . 2_665 ? N3 C2 N2 126.46(18) . . ? N3 C2 N5 120.40(18) . . ? N2 C2 N5 113.14(17) . . ? C2 N3 Ni1 129.97(14) . . ? C2 N3 H3 110.4(15) . . ? Ni1 N3 H3 119.3(15) . . ? C1 N4 C3 124.44(17) . . ? C1 N4 H4 114.5(15) . . ? C3 N4 H4 115.2(15) . . ? C8 C3 C4 121.16(19) . . ? C8 C3 N4 120.59(18) . . ? C4 C3 N4 118.23(18) . . ? C5 C4 C3 118.70(19) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? O1 C5 C6 115.05(18) . . ? O1 C5 C4 123.91(19) . . ? C6 C5 C4 120.99(19) . . ? C5 C6 C7 119.34(19) . . ? C5 C6 H6A 120.3 . . ? C7 C6 H6A 120.3 . . ? O2 C7 C6 115.96(18) . . ? O2 C7 C8 123.00(18) . . ? C6 C7 C8 121.03(19) . . ? C7 C8 C3 118.76(19) . . ? C7 C8 H8A 120.6 . . ? C3 C8 H8A 120.6 . . ? C5 O1 C9 117.53(17) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 O2 C10 116.74(16) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 N5 C11 126.66(17) . . ? C2 N5 H5 115.8(16) . . ? C11 N5 H5 115.6(16) . . ? C16 C11 C12 120.91(18) . . ? C16 C11 N5 117.64(18) . . ? C12 C11 N5 121.34(18) . . ? C13 C12 C11 118.72(19) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? O3 C13 C14 115.81(18) . . ? O3 C13 C12 122.90(19) . . ? C14 C13 C12 121.28(19) . . ? C13 C14 C15 119.01(19) . . ? C13 C14 H14A 120.5 . . ? C15 C14 H14A 120.5 . . ? O4 C15 C16 123.49(18) . . ? O4 C15 C14 115.30(18) . . ? C16 C15 C14 121.20(19) . . ? C15 C16 C11 118.84(18) . . ? C15 C16 H16A 120.6 . . ? C11 C16 H16A 120.6 . . ? C13 O3 C17 117.09(16) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 O4 C18 118.28(16) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C20 C29 120.34(19) . . ? C21 C20 C30 120.13(19) . . ? C29 C20 C30 119.52(18) . . ? C20 C21 C22 120.1(2) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C23 C22 C21 120.9(2) . . ? C23 C22 H22A 119.6 . . ? C21 C22 H22A 119.6 . . ? C22 C23 C24 120.69(19) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? C25 C24 C29 118.70(19) . . ? C25 C24 C23 122.65(19) . . ? C29 C24 C23 118.64(19) . . ? C26 C25 C24 121.0(2) . . ? C26 C25 H25A 119.5 . . ? C24 C25 H25A 119.5 . . ? C25 C26 C27 120.2(2) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C28 C27 C26 120.4(2) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C27 C28 C29 120.24(19) . . ? C27 C28 C31 120.34(19) . . ? C29 C28 C31 119.42(18) . . ? C20 C29 C24 119.37(19) . . ? C20 C29 C28 121.20(18) . . ? C24 C29 C28 119.42(19) . . ? O6 C30 N6 120.20(18) . . ? O6 C30 C20 123.29(18) . . ? N6 C30 C20 116.51(18) . . ? O5 C31 N6 119.95(18) . . ? O5 C31 C28 123.51(18) . . ? N6 C31 C28 116.53(18) . . ? C30 N6 C31 126.80(18) . . ? C30 N6 H6B 115.4(16) . . ? C31 N6 H6B 117.8(16) . . ? 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 N3 Ni1 N1 C1 -1.43(19) 2_665 . . . ? N3 Ni1 N1 C1 178.57(19) . . . . ? N1 Ni1 N1 C1 145(100) 2_665 . . . ? Ni1 N1 C1 N2 3.4(3) . . . 2_665 ? Ni1 N1 C1 N4 -175.70(14) . . . . ? C1 N2 C2 N3 1.5(3) 2_665 . . . ? C1 N2 C2 N5 -178.30(17) 2_665 . . . ? N2 C2 N3 Ni1 -3.5(3) . . . . ? N5 C2 N3 Ni1 176.27(14) . . . . ? N3 Ni1 N3 C2 -136(100) 2_665 . . . ? N1 Ni1 N3 C2 1.82(19) 2_665 . . . ? N1 Ni1 N3 C2 -178.18(19) . . . . ? N1 C1 N4 C3 -7.1(3) . . . . ? N2 C1 N4 C3 173.65(18) 2_665 . . . ? C1 N4 C3 C8 58.0(3) . . . . ? C1 N4 C3 C4 -123.6(2) . . . . ? C8 C3 C4 C5 -1.1(3) . . . . ? N4 C3 C4 C5 -179.48(18) . . . . ? C3 C4 C5 O1 -176.54(19) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? O1 C5 C6 C7 176.97(18) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 O2 179.70(18) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? O2 C7 C8 C3 179.93(18) . . . . ? C6 C7 C8 C3 -1.1(3) . . . . ? C4 C3 C8 C7 1.3(3) . . . . ? N4 C3 C8 C7 179.69(18) . . . . ? C6 C5 O1 C9 -173.46(19) . . . . ? C4 C5 O1 C9 3.9(3) . . . . ? C6 C7 O2 C10 161.16(19) . . . . ? C8 C7 O2 C10 -19.8(3) . . . . ? N3 C2 N5 C11 5.7(3) . . . . ? N2 C2 N5 C11 -174.47(18) . . . . ? C2 N5 C11 C16 -141.2(2) . . . . ? C2 N5 C11 C12 42.7(3) . . . . ? C16 C11 C12 C13 2.2(3) . . . . ? N5 C11 C12 C13 178.24(18) . . . . ? C11 C12 C13 O3 -179.92(18) . . . . ? C11 C12 C13 C14 -1.6(3) . . . . ? O3 C13 C14 C15 178.08(18) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 O4 -179.47(18) . . . . ? C13 C14 C15 C16 1.7(3) . . . . ? O4 C15 C16 C11 -179.84(18) . . . . ? C14 C15 C16 C11 -1.2(3) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? N5 C11 C16 C15 -177.01(18) . . . . ? C14 C13 O3 C17 168.38(18) . . . . ? C12 C13 O3 C17 -13.3(3) . . . . ? C16 C15 O4 C18 -3.6(3) . . . . ? C14 C15 O4 C18 177.65(18) . . . . ? C29 C20 C21 C22 0.9(3) . . . . ? C30 C20 C21 C22 -178.60(19) . . . . ? C20 C21 C22 C23 -0.4(3) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C25 178.8(2) . . . . ? C22 C23 C24 C29 0.1(3) . . . . ? C29 C24 C25 C26 -0.6(3) . . . . ? C23 C24 C25 C26 -179.3(2) . . . . ? C24 C25 C26 C27 -0.1(3) . . . . ? C25 C26 C27 C28 0.8(3) . . . . ? C26 C27 C28 C29 -0.9(3) . . . . ? C26 C27 C28 C31 178.68(18) . . . . ? C21 C20 C29 C24 -0.9(3) . . . . ? C30 C20 C29 C24 178.57(18) . . . . ? C21 C20 C29 C28 -179.80(19) . . . . ? C30 C20 C29 C28 -0.3(3) . . . . ? C25 C24 C29 C20 -178.30(18) . . . . ? C23 C24 C29 C20 0.5(3) . . . . ? C25 C24 C29 C28 0.6(3) . . . . ? C23 C24 C29 C28 179.34(18) . . . . ? C27 C28 C29 C20 179.02(19) . . . . ? C31 C28 C29 C20 -0.5(3) . . . . ? C27 C28 C29 C24 0.2(3) . . . . ? C31 C28 C29 C24 -179.41(18) . . . . ? C21 C20 C30 O6 1.9(3) . . . . ? C29 C20 C30 O6 -177.58(19) . . . . ? C21 C20 C30 N6 -179.07(18) . . . . ? C29 C20 C30 N6 1.4(3) . . . . ? C27 C28 C31 O5 -0.3(3) . . . . ? C29 C28 C31 O5 179.24(19) . . . . ? C27 C28 C31 N6 -179.34(18) . . . . ? C29 C28 C31 N6 0.2(3) . . . . ? O6 C30 N6 C31 177.15(19) . . . . ? C20 C30 N6 C31 -1.9(3) . . . . ? O5 C31 N6 C30 -177.99(19) . . . . ? C28 C31 N6 C30 1.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4 O6 0.85(2) 2.03(2) 2.868(2) 165(2) 2_665 N5 H5 O5 0.87(2) 2.07(3) 2.898(2) 158(2) . N6 H6B N2 0.87(3) 2.16(3) 3.015(2) 168(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.354 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.056