# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name M.K.Whittlesey _publ_contact_author_address ; Building 1 South Claverton Down Claverton Down Bath United Kingdom BA2 7AY ; _publ_contact_author_email m.k.whittlesey@bath.ac.uk loop_ _publ_author_name 'Caroline J. E. Davies' 'Michael J. Page' 'Charles E. Ellul' 'Mary F. Mahon' 'Michael K. Whittlesey' data_h10mkw6 _database_code_depnum_ccdc_archive 'CCDC 776076' #TrackingRef 'bigcif.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 N2 Ni' _chemical_formula_weight 487.35 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' Ni Ni 0.3393 1.1124 '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' _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 9.1890(1) _cell_length_b 11.1750(2) _cell_length_c 13.5820(2) _cell_angle_alpha 94.032(1) _cell_angle_beta 108.115(1) _cell_angle_gamma 99.090(1) _cell_volume 1298.28(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 26126 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.843 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43285 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 30.08 _reflns_number_total 7574 _reflns_number_gt 6422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0382P)^2^+0.4397P] 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 SHELXL _refine_ls_extinction_coef 0.0119(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7574 _refine_ls_number_parameters 318 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _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 0.963230(18) 0.295694(14) 0.719447(13) 0.02376(6) Uani 1 1 d . . . N1 N 0.76494(13) 0.34166(10) 0.83353(8) 0.0263(2) Uani 1 1 d . . . N2 N 0.67712(12) 0.38554(9) 0.66419(8) 0.0236(2) Uani 1 1 d . . . C1 C 0.78038(14) 0.33848(11) 0.73765(9) 0.0226(2) Uani 1 1 d . . . C2 C 0.65999(18) 0.41060(14) 0.86681(12) 0.0363(3) Uani 1 1 d . . . H2A H 0.7113 0.4484 0.9402 0.044 Uiso 1 1 calc R . . H2B H 0.5629 0.3544 0.8626 0.044 Uiso 1 1 calc R . . C3 C 0.62138(19) 0.50882(15) 0.79701(12) 0.0383(3) Uani 1 1 d . . . H3A H 0.5413 0.5485 0.8135 0.046 Uiso 1 1 calc R . . H3B H 0.7159 0.5720 0.8092 0.046 Uiso 1 1 calc R . . C4 C 0.56111(16) 0.45210(14) 0.68407(11) 0.0325(3) Uani 1 1 d . . . H4A H 0.4606 0.3953 0.6698 0.039 Uiso 1 1 calc R . . H4B H 0.5439 0.5166 0.6376 0.039 Uiso 1 1 calc R . . C5 C 0.88204(15) 0.29667(12) 0.91208(10) 0.0273(3) Uani 1 1 d . . . C6 C 1.03822(16) 0.33568(12) 0.91858(10) 0.0284(3) Uani 1 1 d . . . C7 C 1.15122(16) 0.28571(12) 0.99005(11) 0.0320(3) Uani 1 1 d . . . H7 H 1.2577 0.3109 0.9962 0.038 Uiso 1 1 calc R . . C8 C 1.11307(18) 0.20074(14) 1.05209(11) 0.0362(3) Uani 1 1 d . . . C9 C 0.95743(18) 0.16444(15) 1.04297(11) 0.0388(3) Uani 1 1 d . . . H9 H 0.9302 0.1065 1.0853 0.047 Uiso 1 1 calc R . . C10 C 0.83952(17) 0.21109(14) 0.97288(11) 0.0333(3) Uani 1 1 d . . . C11 C 1.07741(16) 0.41611(12) 0.84444(11) 0.0309(3) Uani 1 1 d . . . H11A H 1.1908 0.4361 0.8561 0.041(5) Uiso 1 1 calc R . . H11B H 1.0340 0.4918 0.8438 0.031(4) Uiso 1 1 calc R . . C12 C 1.2391(2) 0.14854(17) 1.12711(14) 0.0482(4) Uani 1 1 d . . . H12A H 1.2660 0.1919 1.1975 0.072 Uiso 1 1 calc R . . H12B H 1.3318 0.1583 1.1051 0.072 Uiso 1 1 calc R . . H12C H 1.2014 0.0615 1.1274 0.072 Uiso 1 1 calc R . . C13 C 0.67098(19) 0.16310(17) 0.96173(13) 0.0451(4) Uani 1 1 d . . . H13A H 0.6308 0.2251 0.9949 0.068 Uiso 1 1 calc R . . H13B H 0.6639 0.0888 0.9955 0.068 Uiso 1 1 calc R . . H13C H 0.6091 0.1444 0.8875 0.068 Uiso 1 1 calc R . . C14 C 0.67959(14) 0.37142(11) 0.55866(10) 0.0227(2) Uani 1 1 d . . . C15 C 0.58882(14) 0.26747(11) 0.49119(10) 0.0244(2) Uani 1 1 d . . . C16 C 0.59916(15) 0.25188(12) 0.39084(10) 0.0273(3) Uani 1 1 d . . . H16 H 0.5391 0.1813 0.3443 0.033 Uiso 1 1 calc R . . C17 C 0.69535(15) 0.33719(12) 0.35717(10) 0.0282(3) Uani 1 1 d . . . C18 C 0.77719(15) 0.44291(12) 0.42500(11) 0.0286(3) Uani 1 1 d . . . H18 H 0.8397 0.5033 0.4019 0.034 Uiso 1 1 calc R . . C19 C 0.76986(14) 0.46240(11) 0.52543(10) 0.0258(2) Uani 1 1 d . . . C20 C 0.48588(16) 0.17396(12) 0.52712(11) 0.0318(3) Uani 1 1 d . . . H20A H 0.4417 0.1029 0.4734 0.048 Uiso 1 1 calc R . . H20B H 0.4013 0.2098 0.5392 0.048 Uiso 1 1 calc R . . H20C H 0.5477 0.1483 0.5922 0.048 Uiso 1 1 calc R . . C21 C 0.71185(18) 0.31478(15) 0.25060(11) 0.0372(3) Uani 1 1 d . . . H21A H 0.7323 0.3931 0.2245 0.056 Uiso 1 1 calc R . . H21B H 0.6152 0.2646 0.2025 0.056 Uiso 1 1 calc R . . H21C H 0.7987 0.2721 0.2556 0.056 Uiso 1 1 calc R . . C22 C 0.85433(17) 0.57896(12) 0.59678(13) 0.0351(3) Uani 1 1 d . . . H22A H 0.9215 0.6275 0.5647 0.053 Uiso 1 1 calc R . . H22B H 0.9182 0.5592 0.6639 0.053 Uiso 1 1 calc R . . H22C H 0.7781 0.6259 0.6081 0.053 Uiso 1 1 calc R . . C23 C 0.88375(15) 0.13053(12) 0.62121(10) 0.0262(2) Uani 1 1 d D . . C24 C 1.01578(17) 0.20383(13) 0.61152(11) 0.0309(3) Uani 1 1 d D . . C25 C 1.15518(17) 0.24395(13) 0.69608(13) 0.0347(3) Uani 1 1 d D . . C26 C 1.22770(16) 0.16615(14) 0.77873(13) 0.0361(3) Uani 1 1 d . . . H26A H 1.1575 0.1475 0.8203 0.043 Uiso 1 1 calc R . . H26B H 1.3274 0.2148 0.8266 0.043 Uiso 1 1 calc R . . C27 C 1.25953(18) 0.04483(15) 0.73607(13) 0.0402(3) Uani 1 1 d . . . H27A H 1.3515 0.0637 0.7126 0.048 Uiso 1 1 calc R . . H27B H 1.2875 -0.0048 0.7943 0.048 Uiso 1 1 calc R . . C28 C 1.12633(19) -0.03312(14) 0.64597(12) 0.0380(3) Uani 1 1 d . . . H28A H 1.1622 -0.1077 0.6269 0.046 Uiso 1 1 calc R . . H28B H 1.1078 0.0130 0.5850 0.046 Uiso 1 1 calc R . . C29 C 0.96999(18) -0.07281(13) 0.66313(12) 0.0353(3) Uani 1 1 d . . . H29A H 0.9863 -0.1252 0.7200 0.042 Uiso 1 1 calc R . . H29B H 0.8976 -0.1240 0.5988 0.042 Uiso 1 1 calc R . . C30 C 0.88931(16) 0.03004(12) 0.69079(10) 0.0276(3) Uani 1 1 d . . . H30A H 0.7814 -0.0063 0.6858 0.033 Uiso 1 1 calc R . . H30B H 0.9453 0.0665 0.7641 0.033 Uiso 1 1 calc R . . H23 H 0.7889(11) 0.1188(14) 0.5608(8) 0.030(4) Uiso 1 1 d D . . H24 H 0.999(2) 0.2467(14) 0.5494(9) 0.040(5) Uiso 1 1 d D . . H25 H 1.2299(17) 0.3073(13) 0.6819(15) 0.048(5) Uiso 1 1 d 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 0.02204(9) 0.02114(9) 0.02858(9) 0.00666(6) 0.00740(6) 0.00574(6) N1 0.0270(5) 0.0271(5) 0.0245(5) 0.0022(4) 0.0068(4) 0.0076(4) N2 0.0209(5) 0.0233(5) 0.0255(5) 0.0022(4) 0.0049(4) 0.0068(4) C1 0.0213(5) 0.0187(5) 0.0245(6) 0.0011(4) 0.0040(4) 0.0020(4) C2 0.0396(8) 0.0416(8) 0.0315(7) 0.0010(6) 0.0143(6) 0.0152(6) C3 0.0421(8) 0.0392(8) 0.0360(7) -0.0005(6) 0.0108(6) 0.0212(7) C4 0.0270(6) 0.0374(7) 0.0338(7) 0.0025(6) 0.0073(5) 0.0147(5) C5 0.0297(6) 0.0273(6) 0.0203(6) 0.0000(5) 0.0029(5) 0.0045(5) C6 0.0305(6) 0.0229(6) 0.0255(6) 0.0009(5) 0.0025(5) 0.0016(5) C7 0.0292(7) 0.0288(6) 0.0292(6) 0.0029(5) -0.0006(5) 0.0007(5) C8 0.0365(7) 0.0347(7) 0.0282(7) 0.0075(6) -0.0015(6) 0.0031(6) C9 0.0407(8) 0.0413(8) 0.0285(7) 0.0122(6) 0.0045(6) 0.0010(6) C10 0.0338(7) 0.0377(7) 0.0246(6) 0.0046(5) 0.0062(5) 0.0020(6) C11 0.0274(6) 0.0250(6) 0.0350(7) 0.0066(5) 0.0037(5) 0.0012(5) C12 0.0421(9) 0.0482(9) 0.0436(9) 0.0200(7) -0.0024(7) 0.0052(7) C13 0.0364(8) 0.0564(10) 0.0422(9) 0.0179(8) 0.0130(7) 0.0026(7) C14 0.0200(5) 0.0224(5) 0.0250(6) 0.0054(4) 0.0040(4) 0.0077(4) C15 0.0211(5) 0.0232(6) 0.0268(6) 0.0050(5) 0.0037(4) 0.0057(4) C16 0.0250(6) 0.0273(6) 0.0263(6) 0.0027(5) 0.0023(5) 0.0080(5) C17 0.0274(6) 0.0324(6) 0.0277(6) 0.0105(5) 0.0073(5) 0.0147(5) C18 0.0267(6) 0.0267(6) 0.0356(7) 0.0130(5) 0.0105(5) 0.0099(5) C19 0.0221(6) 0.0212(5) 0.0336(6) 0.0073(5) 0.0060(5) 0.0075(4) C20 0.0291(6) 0.0282(6) 0.0337(7) 0.0019(5) 0.0081(5) -0.0022(5) C21 0.0392(8) 0.0466(8) 0.0306(7) 0.0125(6) 0.0124(6) 0.0163(7) C22 0.0339(7) 0.0237(6) 0.0466(8) 0.0044(6) 0.0132(6) 0.0018(5) C23 0.0296(6) 0.0266(6) 0.0234(6) 0.0043(5) 0.0067(5) 0.0114(5) C24 0.0383(7) 0.0322(7) 0.0336(7) 0.0145(5) 0.0201(6) 0.0177(6) C25 0.0279(7) 0.0319(7) 0.0521(9) 0.0143(6) 0.0199(6) 0.0100(5) C26 0.0239(6) 0.0347(7) 0.0462(8) 0.0061(6) 0.0051(6) 0.0084(5) C27 0.0357(8) 0.0441(8) 0.0461(9) 0.0127(7) 0.0127(7) 0.0213(7) C28 0.0497(9) 0.0389(8) 0.0330(7) 0.0094(6) 0.0141(6) 0.0273(7) C29 0.0455(8) 0.0253(6) 0.0322(7) 0.0049(5) 0.0059(6) 0.0122(6) C30 0.0301(6) 0.0241(6) 0.0272(6) 0.0050(5) 0.0075(5) 0.0041(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.8996(12) . ? Ni1 C24 1.9547(14) . ? Ni1 C11 1.9796(14) . ? Ni1 C25 2.0471(14) . ? Ni1 C23 2.0838(13) . ? N1 C1 1.3516(16) . ? N1 C5 1.4427(16) . ? N1 C2 1.4781(17) . ? N2 C1 1.3473(15) . ? N2 C14 1.4384(16) . ? N2 C4 1.4710(16) . ? C2 C3 1.513(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.512(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.3939(19) . ? C5 C6 1.4056(19) . ? C6 C7 1.4017(19) . ? C6 C11 1.4839(19) . ? C7 C8 1.388(2) . ? C7 H7 0.9500 . ? C8 C9 1.387(2) . ? C8 C12 1.511(2) . ? C9 C10 1.400(2) . ? C9 H9 0.9500 . ? C10 C13 1.513(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.3977(17) . ? C14 C19 1.3987(17) . ? C15 C16 1.3962(18) . ? C15 C20 1.5071(18) . ? C16 C17 1.3949(19) . ? C16 H16 0.9500 . ? C17 C18 1.395(2) . ? C17 C21 1.5094(19) . ? C18 C19 1.3901(19) . ? C18 H18 0.9500 . ? C19 C22 1.5079(19) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.4002(19) . ? C23 C30 1.5146(18) . ? C23 H23 0.977(5) . ? C24 C25 1.411(2) . ? C24 H24 0.982(5) . ? C25 C26 1.522(2) . ? C25 H25 0.979(5) . ? C26 C27 1.543(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.528(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.528(2) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.5471(19) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? 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 Ni1 C24 136.86(6) . . ? C1 Ni1 C11 85.36(6) . . ? C24 Ni1 C11 136.59(6) . . ? C1 Ni1 C25 177.85(6) . . ? C24 Ni1 C25 41.22(6) . . ? C11 Ni1 C25 96.71(6) . . ? C1 Ni1 C23 104.39(5) . . ? C24 Ni1 C23 40.41(6) . . ? C11 Ni1 C23 160.42(5) . . ? C25 Ni1 C23 73.46(6) . . ? C1 N1 C5 116.04(10) . . ? C1 N1 C2 123.90(11) . . ? C5 N1 C2 118.68(11) . . ? C1 N2 C14 118.55(10) . . ? C1 N2 C4 124.57(11) . . ? C14 N2 C4 116.88(10) . . ? N2 C1 N1 117.27(11) . . ? N2 C1 Ni1 122.80(9) . . ? N1 C1 Ni1 118.99(9) . . ? N1 C2 C3 109.64(12) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 109.38(12) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N2 C4 C3 108.53(11) . . ? N2 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? N2 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? C10 C5 C6 122.00(12) . . ? C10 C5 N1 120.72(12) . . ? C6 C5 N1 117.11(11) . . ? C7 C6 C5 117.17(12) . . ? C7 C6 C11 122.11(13) . . ? C5 C6 C11 120.41(12) . . ? C8 C7 C6 122.35(14) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C9 C8 C7 118.62(13) . . ? C9 C8 C12 121.08(14) . . ? C7 C8 C12 120.30(14) . . ? C8 C9 C10 121.57(14) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C5 C10 C9 118.30(13) . . ? C5 C10 C13 122.27(13) . . ? C9 C10 C13 119.37(13) . . ? C6 C11 Ni1 94.32(8) . . ? C6 C11 H11A 112.9 . . ? Ni1 C11 H11A 112.9 . . ? C6 C11 H11B 112.9 . . ? Ni1 C11 H11B 112.9 . . ? H11A C11 H11B 110.3 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 121.62(12) . . ? C15 C14 N2 118.81(11) . . ? C19 C14 N2 119.56(11) . . ? C16 C15 C14 118.05(11) . . ? C16 C15 C20 121.28(11) . . ? C14 C15 C20 120.65(12) . . ? C17 C16 C15 121.76(12) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C18 C17 C16 118.26(12) . . ? C18 C17 C21 120.94(13) . . ? C16 C17 C21 120.79(13) . . ? C19 C18 C17 121.84(12) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C14 118.23(12) . . ? C18 C19 C22 121.39(12) . . ? C14 C19 C22 120.37(12) . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C30 124.22(12) . . ? C24 C23 Ni1 64.83(8) . . ? C30 C23 Ni1 106.81(8) . . ? C24 C23 H23 116.0(9) . . ? C30 C23 H23 114.5(10) . . ? Ni1 C23 H23 120.7(10) . . ? C23 C24 C25 122.98(12) . . ? C23 C24 Ni1 74.75(8) . . ? C25 C24 Ni1 72.90(9) . . ? C23 C24 H24 116.1(10) . . ? C25 C24 H24 118.6(11) . . ? Ni1 C24 H24 109.7(10) . . ? C24 C25 C26 124.99(13) . . ? C24 C25 Ni1 65.88(8) . . ? C26 C25 Ni1 110.71(10) . . ? C24 C25 H25 114.1(11) . . ? C26 C25 H25 114.7(11) . . ? Ni1 C25 H25 117.0(11) . . ? C25 C26 C27 115.10(13) . . ? C25 C26 H26A 108.5 . . ? C27 C26 H26A 108.5 . . ? C25 C26 H26B 108.5 . . ? C27 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? C28 C27 C26 116.41(12) . . ? C28 C27 H27A 108.2 . . ? C26 C27 H27A 108.2 . . ? C28 C27 H27B 108.2 . . ? C26 C27 H27B 108.2 . . ? H27A C27 H27B 107.3 . . ? C27 C28 C29 117.93(13) . . ? C27 C28 H28A 107.8 . . ? C29 C28 H28A 107.8 . . ? C27 C28 H28B 107.8 . . ? C29 C28 H28B 107.8 . . ? H28A C28 H28B 107.2 . . ? C28 C29 C30 116.80(12) . . ? C28 C29 H29A 108.1 . . ? C30 C29 H29A 108.1 . . ? C28 C29 H29B 108.1 . . ? C30 C29 H29B 108.1 . . ? H29A C29 H29B 107.3 . . ? C23 C30 C29 113.89(11) . . ? C23 C30 H30A 108.8 . . ? C29 C30 H30A 108.8 . . ? C23 C30 H30B 108.8 . . ? C29 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N2 C1 N1 -173.22(10) . . . . ? C4 N2 C1 N1 7.29(18) . . . . ? C14 N2 C1 Ni1 18.04(15) . . . . ? C4 N2 C1 Ni1 -161.45(10) . . . . ? C5 N1 C1 N2 -176.79(11) . . . . ? C2 N1 C1 N2 -10.39(18) . . . . ? C5 N1 C1 Ni1 -7.59(14) . . . . ? C2 N1 C1 Ni1 158.80(11) . . . . ? C24 Ni1 C1 N2 -48.10(13) . . . . ? C11 Ni1 C1 N2 120.26(10) . . . . ? C25 Ni1 C1 N2 -74.4(15) . . . . ? C23 Ni1 C1 N2 -76.97(10) . . . . ? C24 Ni1 C1 N1 143.34(9) . . . . ? C11 Ni1 C1 N1 -48.30(10) . . . . ? C25 Ni1 C1 N1 117.1(15) . . . . ? C23 Ni1 C1 N1 114.46(10) . . . . ? C1 N1 C2 C3 -20.44(19) . . . . ? C5 N1 C2 C3 145.62(13) . . . . ? N1 C2 C3 C4 52.63(17) . . . . ? C1 N2 C4 C3 26.05(18) . . . . ? C14 N2 C4 C3 -153.45(12) . . . . ? C2 C3 C4 N2 -54.92(16) . . . . ? C1 N1 C5 C10 -129.99(13) . . . . ? C2 N1 C5 C10 62.87(17) . . . . ? C1 N1 C5 C6 45.30(16) . . . . ? C2 N1 C5 C6 -121.85(14) . . . . ? C10 C5 C6 C7 -0.6(2) . . . . ? N1 C5 C6 C7 -175.84(11) . . . . ? C10 C5 C6 C11 173.10(13) . . . . ? N1 C5 C6 C11 -2.11(18) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? C11 C6 C7 C8 -173.27(14) . . . . ? C6 C7 C8 C9 -0.2(2) . . . . ? C6 C7 C8 C12 179.31(15) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C12 C8 C9 C10 -179.24(16) . . . . ? C6 C5 C10 C9 0.7(2) . . . . ? N1 C5 C10 C9 175.75(13) . . . . ? C6 C5 C10 C13 -176.29(14) . . . . ? N1 C5 C10 C13 -1.2(2) . . . . ? C8 C9 C10 C5 -0.5(2) . . . . ? C8 C9 C10 C13 176.58(15) . . . . ? C7 C6 C11 Ni1 111.44(12) . . . . ? C5 C6 C11 Ni1 -61.97(13) . . . . ? C1 Ni1 C11 C6 74.87(9) . . . . ? C24 Ni1 C11 C6 -116.71(10) . . . . ? C25 Ni1 C11 C6 -104.58(9) . . . . ? C23 Ni1 C11 C6 -46.2(2) . . . . ? C1 N2 C14 C15 89.19(14) . . . . ? C4 N2 C14 C15 -91.28(14) . . . . ? C1 N2 C14 C19 -91.96(14) . . . . ? C4 N2 C14 C19 87.57(14) . . . . ? C19 C14 C15 C16 4.65(18) . . . . ? N2 C14 C15 C16 -176.53(10) . . . . ? C19 C14 C15 C20 -176.71(12) . . . . ? N2 C14 C15 C20 2.11(17) . . . . ? C14 C15 C16 C17 -0.66(18) . . . . ? C20 C15 C16 C17 -179.29(12) . . . . ? C15 C16 C17 C18 -2.87(19) . . . . ? C15 C16 C17 C21 176.37(12) . . . . ? C16 C17 C18 C19 2.60(18) . . . . ? C21 C17 C18 C19 -176.64(12) . . . . ? C17 C18 C19 C14 1.20(18) . . . . ? C17 C18 C19 C22 -177.83(12) . . . . ? C15 C14 C19 C18 -4.92(18) . . . . ? N2 C14 C19 C18 176.27(11) . . . . ? C15 C14 C19 C22 174.12(12) . . . . ? N2 C14 C19 C22 -4.69(17) . . . . ? C1 Ni1 C23 C24 149.38(8) . . . . ? C11 Ni1 C23 C24 -92.41(18) . . . . ? C25 Ni1 C23 C24 -30.52(8) . . . . ? C1 Ni1 C23 C30 -90.14(9) . . . . ? C24 Ni1 C23 C30 120.48(12) . . . . ? C11 Ni1 C23 C30 28.1(2) . . . . ? C25 Ni1 C23 C30 89.96(9) . . . . ? C30 C23 C24 C25 -36.5(2) . . . . ? Ni1 C23 C24 C25 57.31(12) . . . . ? C30 C23 C24 Ni1 -93.84(12) . . . . ? C1 Ni1 C24 C23 -46.17(11) . . . . ? C11 Ni1 C24 C23 150.84(8) . . . . ? C25 Ni1 C24 C23 132.38(11) . . . . ? C1 Ni1 C24 C25 -178.56(8) . . . . ? C11 Ni1 C24 C25 18.46(12) . . . . ? C23 Ni1 C24 C25 -132.38(11) . . . . ? C23 C24 C25 C26 41.0(2) . . . . ? Ni1 C24 C25 C26 99.18(14) . . . . ? C23 C24 C25 Ni1 -58.16(12) . . . . ? C1 Ni1 C25 C24 27.3(15) . . . . ? C11 Ni1 C25 C24 -167.34(8) . . . . ? C23 Ni1 C25 C24 29.97(8) . . . . ? C1 Ni1 C25 C26 -92.8(15) . . . . ? C24 Ni1 C25 C26 -120.16(14) . . . . ? C11 Ni1 C25 C26 72.50(11) . . . . ? C23 Ni1 C25 C26 -90.19(11) . . . . ? C24 C25 C26 C27 55.25(19) . . . . ? Ni1 C25 C26 C27 129.66(12) . . . . ? C25 C26 C27 C28 -47.57(19) . . . . ? C26 C27 C28 C29 -57.29(19) . . . . ? C27 C28 C29 C30 59.38(17) . . . . ? C24 C23 C30 C29 -60.42(17) . . . . ? Ni1 C23 C30 C29 -131.04(10) . . . . ? C28 C29 C30 C23 47.24(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.317 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.054 #===end data_k10mkw8 _database_code_depnum_ccdc_archive 'CCDC 776077' #TrackingRef 'bigcif.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 N2' _chemical_formula_weight 318.45 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7360(2) _cell_length_b 7.7970(1) _cell_length_c 18.0210(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.5110(10) _cell_angle_gamma 90.00 _cell_volume 1786.17(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 22858 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33532 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4088 _reflns_number_gt 3241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0542P)^2^+0.5429P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4088 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1076 _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 N1 N 0.06793(8) -0.00821(14) 0.19542(6) 0.0291(3) Uani 1 1 d . . . N2 N 0.21323(8) 0.09661(14) 0.13068(6) 0.0261(2) Uani 1 1 d . . . C1 C 0.11057(10) 0.11374(16) 0.15103(7) 0.0254(3) Uani 1 1 d . . . C2 C 0.12435(11) -0.16718(18) 0.21302(9) 0.0362(3) Uani 1 1 d . . . H2A H 0.1096 -0.2516 0.1727 0.043 Uiso 1 1 calc R . . H2B H 0.1001 -0.2161 0.2597 0.043 Uiso 1 1 calc R . . C3 C 0.24065(11) -0.13235(19) 0.22171(8) 0.0378(3) Uani 1 1 d . . . H3A H 0.2787 -0.2415 0.2316 0.045 Uiso 1 1 calc R . . H3B H 0.2556 -0.0556 0.2648 0.045 Uiso 1 1 calc R . . C4 C 0.27961(11) -0.04981(18) 0.15257(8) 0.0338(3) Uani 1 1 d . . . H4A H 0.3532 -0.0112 0.1624 0.041 Uiso 1 1 calc R . . H4B H 0.2781 -0.1347 0.1117 0.041 Uiso 1 1 calc R . . C5 C 0.23765(10) 0.23933(16) 0.08788(7) 0.0253(3) Uani 1 1 d . . . C6 C 0.14728(10) 0.34637(16) 0.08340(7) 0.0253(3) Uani 1 1 d . . . C7 C 0.06812(10) 0.26451(16) 0.12375(7) 0.0269(3) Uani 1 1 d . . . H7 H -0.0007 0.3064 0.1304 0.032 Uiso 1 1 calc R . . C8 C 0.32804(10) 0.28050(17) 0.05108(7) 0.0291(3) Uani 1 1 d . . . C9 C 0.32449(10) 0.43306(18) 0.01079(7) 0.0313(3) Uani 1 1 d . . . H9 H 0.3847 0.4647 -0.0146 0.038 Uiso 1 1 calc R . . C10 C 0.23699(11) 0.54260(17) 0.00562(7) 0.0304(3) Uani 1 1 d . . . C11 C 0.14854(10) 0.49866(17) 0.04220(7) 0.0285(3) Uani 1 1 d . . . H11 H 0.0887 0.5716 0.0394 0.034 Uiso 1 1 calc R . . C12 C 0.42628(11) 0.1712(2) 0.05181(9) 0.0429(4) Uani 1 1 d . . . H12A H 0.4732 0.2156 0.0152 0.064 Uiso 1 1 calc R . . H12B H 0.4069 0.0526 0.0393 0.064 Uiso 1 1 calc R . . H12C H 0.4623 0.1746 0.1014 0.064 Uiso 1 1 calc R . . C13 C 0.23984(12) 0.70334(19) -0.04089(8) 0.0398(3) Uani 1 1 d . . . H13A H 0.3085 0.7128 -0.0623 0.060 Uiso 0.50 1 calc PR . . H13B H 0.2285 0.8036 -0.0096 0.060 Uiso 0.50 1 calc PR . . H13C H 0.1844 0.6980 -0.0810 0.060 Uiso 0.50 1 calc PR . . H13D H 0.1724 0.7635 -0.0396 0.060 Uiso 0.50 1 calc PR . . H13E H 0.2524 0.6726 -0.0923 0.060 Uiso 0.50 1 calc PR . . H13F H 0.2966 0.7782 -0.0209 0.060 Uiso 0.50 1 calc PR . . C14 C -0.04246(10) 0.00025(16) 0.20726(7) 0.0263(3) Uani 1 1 d . . . C15 C -0.11682(11) -0.05107(17) 0.15139(7) 0.0298(3) Uani 1 1 d . . . C16 C -0.22292(11) -0.03938(17) 0.16567(8) 0.0328(3) Uani 1 1 d . . . H16 H -0.2743 -0.0717 0.1278 0.039 Uiso 1 1 calc R . . C17 C -0.25598(11) 0.01765(17) 0.23309(8) 0.0328(3) Uani 1 1 d . . . C18 C -0.17994(11) 0.06337(17) 0.28812(8) 0.0320(3) Uani 1 1 d . . . H18 H -0.2015 0.0995 0.3352 0.038 Uiso 1 1 calc R . . C19 C -0.07304(10) 0.05771(16) 0.27619(7) 0.0290(3) Uani 1 1 d . . . C20 C 0.00743(12) 0.1161(2) 0.33543(8) 0.0404(3) Uani 1 1 d . . . H20A H 0.0781 0.1031 0.3174 0.061 Uiso 0.50 1 calc PR . . H20B H 0.0015 0.0464 0.3802 0.061 Uiso 0.50 1 calc PR . . H20C H -0.0049 0.2369 0.3472 0.061 Uiso 0.50 1 calc PR . . H20D H -0.0283 0.1545 0.3791 0.061 Uiso 0.50 1 calc PR . . H20E H 0.0483 0.2112 0.3164 0.061 Uiso 0.50 1 calc PR . . H20F H 0.0547 0.0207 0.3494 0.061 Uiso 0.50 1 calc PR . . C21 C -0.08462(13) -0.1197(2) 0.07818(8) 0.0411(4) Uani 1 1 d . . . H21A H -0.0077 -0.1188 0.0776 0.062 Uiso 0.50 1 calc PR . . H21B H -0.1147 -0.0475 0.0377 0.062 Uiso 0.50 1 calc PR . . H21C H -0.1105 -0.2374 0.0715 0.062 Uiso 0.50 1 calc PR . . H21D H -0.1475 -0.1503 0.0470 0.062 Uiso 0.50 1 calc PR . . H21E H -0.0406 -0.2216 0.0868 0.062 Uiso 0.50 1 calc PR . . H21F H -0.0448 -0.0318 0.0531 0.062 Uiso 0.50 1 calc PR . . C22 C -0.37129(12) 0.0317(2) 0.24687(11) 0.0484(4) Uani 1 1 d . . . H22A H -0.4134 -0.0059 0.2025 0.073 Uiso 0.50 1 calc PR . . H22B H -0.3884 0.1511 0.2580 0.073 Uiso 0.50 1 calc PR . . H22C H -0.3870 -0.0412 0.2891 0.073 Uiso 0.50 1 calc PR . . H22D H -0.3792 0.0753 0.2972 0.073 Uiso 0.50 1 calc PR . . H22E H -0.4041 -0.0817 0.2417 0.073 Uiso 0.50 1 calc PR . . H22F H -0.4055 0.1105 0.2106 0.073 Uiso 0.50 1 calc PR . . 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 0.0272(6) 0.0298(6) 0.0308(6) 0.0061(4) 0.0043(4) 0.0040(4) N2 0.0243(5) 0.0287(5) 0.0252(5) 0.0023(4) 0.0024(4) 0.0050(4) C1 0.0248(6) 0.0293(6) 0.0219(6) -0.0017(5) 0.0016(5) 0.0011(5) C2 0.0346(7) 0.0321(7) 0.0422(8) 0.0098(6) 0.0042(6) 0.0057(6) C3 0.0333(7) 0.0386(8) 0.0414(8) 0.0125(6) 0.0009(6) 0.0078(6) C4 0.0316(7) 0.0336(7) 0.0363(7) 0.0059(6) 0.0029(6) 0.0099(6) C5 0.0270(6) 0.0276(6) 0.0212(6) -0.0008(5) -0.0002(5) 0.0018(5) C6 0.0262(6) 0.0278(6) 0.0217(6) -0.0027(5) -0.0008(5) 0.0019(5) C7 0.0246(6) 0.0288(6) 0.0273(6) 0.0006(5) 0.0016(5) 0.0032(5) C8 0.0260(6) 0.0358(7) 0.0255(6) -0.0011(5) 0.0023(5) 0.0021(5) C9 0.0297(7) 0.0373(7) 0.0271(6) 0.0020(5) 0.0041(5) -0.0025(5) C10 0.0347(7) 0.0305(7) 0.0257(6) 0.0002(5) -0.0001(5) -0.0016(5) C11 0.0292(7) 0.0278(6) 0.0281(7) -0.0007(5) -0.0006(5) 0.0033(5) C12 0.0316(7) 0.0510(9) 0.0473(9) 0.0107(7) 0.0132(6) 0.0104(7) C13 0.0451(8) 0.0346(7) 0.0399(8) 0.0073(6) 0.0030(6) -0.0015(6) C14 0.0255(6) 0.0254(6) 0.0282(6) 0.0041(5) 0.0030(5) 0.0007(5) C15 0.0341(7) 0.0257(6) 0.0293(7) 0.0030(5) -0.0010(5) 0.0009(5) C16 0.0302(7) 0.0286(6) 0.0387(7) 0.0036(6) -0.0052(6) -0.0028(5) C17 0.0279(7) 0.0242(6) 0.0466(8) 0.0049(6) 0.0048(6) -0.0010(5) C18 0.0339(7) 0.0287(6) 0.0343(7) 0.0005(6) 0.0100(6) -0.0008(5) C19 0.0318(7) 0.0260(6) 0.0292(7) 0.0015(5) 0.0026(5) -0.0019(5) C20 0.0400(8) 0.0498(9) 0.0313(7) -0.0059(7) 0.0009(6) -0.0035(7) C21 0.0461(9) 0.0450(8) 0.0316(7) -0.0061(6) -0.0024(6) 0.0025(7) C22 0.0294(8) 0.0458(9) 0.0708(11) 0.0005(8) 0.0081(7) -0.0005(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 1.3755(16) . ? N1 C14 1.4364(16) . ? N1 C2 1.4579(17) . ? N2 C1 1.3858(16) . ? N2 C5 1.3997(16) . ? N2 C4 1.4604(16) . ? C1 C7 1.3724(18) . ? C2 C3 1.505(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5128(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C8 1.4007(18) . ? C5 C6 1.4199(17) . ? C6 C11 1.4011(18) . ? C6 C7 1.4291(18) . ? C7 H7 0.9500 . ? C8 C9 1.3929(19) . ? C8 C12 1.5132(19) . ? C9 C10 1.4027(19) . ? C9 H9 0.9500 . ? C10 C11 1.3827(19) . ? C10 C13 1.5093(19) . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 H13D 0.9800 . ? C13 H13E 0.9800 . ? C13 H13F 0.9800 . ? C14 C15 1.3978(18) . ? C14 C19 1.3982(18) . ? C15 C16 1.3939(19) . ? C15 C21 1.5036(19) . ? C16 C17 1.383(2) . ? C16 H16 0.9500 . ? C17 C18 1.390(2) . ? C17 C22 1.5083(19) . ? C18 C19 1.3919(18) . ? C18 H18 0.9500 . ? C19 C20 1.5044(19) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C20 H20D 0.9800 . ? C20 H20E 0.9800 . ? C20 H20F 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 H21D 0.9800 . ? C21 H21E 0.9800 . ? C21 H21F 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22 H22D 0.9800 . ? C22 H22E 0.9800 . ? C22 H22F 0.9800 . ? 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 C14 118.66(10) . . ? C1 N1 C2 120.49(11) . . ? C14 N1 C2 118.72(10) . . ? C1 N2 C5 108.31(10) . . ? C1 N2 C4 122.94(11) . . ? C5 N2 C4 128.74(10) . . ? C7 C1 N1 129.76(11) . . ? C7 C1 N2 110.19(11) . . ? N1 C1 N2 119.98(11) . . ? N1 C2 C3 109.77(11) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 111.19(12) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N2 C4 C3 109.96(11) . . ? N2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N2 C5 C8 131.29(11) . . ? N2 C5 C6 106.98(11) . . ? C8 C5 C6 121.68(12) . . ? C11 C6 C5 119.52(12) . . ? C11 C6 C7 132.80(12) . . ? C5 C6 C7 107.64(11) . . ? C1 C7 C6 106.87(11) . . ? C1 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C9 C8 C5 116.17(12) . . ? C9 C8 C12 119.08(12) . . ? C5 C8 C12 124.75(12) . . ? C8 C9 C10 123.71(12) . . ? C8 C9 H9 118.1 . . ? C10 C9 H9 118.1 . . ? C11 C10 C9 118.99(12) . . ? C11 C10 C13 121.23(12) . . ? C9 C10 C13 119.77(12) . . ? C10 C11 C6 119.92(12) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C13 H13D 109.5 . . ? H13A C13 H13D 141.1 . . ? H13B C13 H13D 56.3 . . ? H13C C13 H13D 56.3 . . ? C10 C13 H13E 109.5 . . ? H13A C13 H13E 56.3 . . ? H13B C13 H13E 141.1 . . ? H13C C13 H13E 56.3 . . ? H13D C13 H13E 109.5 . . ? C10 C13 H13F 109.5 . . ? H13A C13 H13F 56.3 . . ? H13B C13 H13F 56.3 . . ? H13C C13 H13F 141.1 . . ? H13D C13 H13F 109.5 . . ? H13E C13 H13F 109.5 . . ? C15 C14 C19 121.23(12) . . ? C15 C14 N1 120.39(11) . . ? C19 C14 N1 118.37(11) . . ? C16 C15 C14 118.03(12) . . ? C16 C15 C21 120.32(12) . . ? C14 C15 C21 121.65(12) . . ? C17 C16 C15 122.26(13) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 118.22(12) . . ? C16 C17 C22 121.30(14) . . ? C18 C17 C22 120.47(14) . . ? C17 C18 C19 121.82(12) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C18 C19 C14 118.40(12) . . ? C18 C19 C20 120.74(12) . . ? C14 C19 C20 120.84(12) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C20 H20D 109.5 . . ? H20A C20 H20D 141.1 . . ? H20B C20 H20D 56.3 . . ? H20C C20 H20D 56.3 . . ? C19 C20 H20E 109.5 . . ? H20A C20 H20E 56.3 . . ? H20B C20 H20E 141.1 . . ? H20C C20 H20E 56.3 . . ? H20D C20 H20E 109.5 . . ? C19 C20 H20F 109.5 . . ? H20A C20 H20F 56.3 . . ? H20B C20 H20F 56.3 . . ? H20C C20 H20F 141.1 . . ? H20D C20 H20F 109.5 . . ? H20E C20 H20F 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 C21 H21D 109.5 . . ? H21A C21 H21D 141.1 . . ? H21B C21 H21D 56.3 . . ? H21C C21 H21D 56.3 . . ? C15 C21 H21E 109.5 . . ? H21A C21 H21E 56.3 . . ? H21B C21 H21E 141.1 . . ? H21C C21 H21E 56.3 . . ? H21D C21 H21E 109.5 . . ? C15 C21 H21F 109.5 . . ? H21A C21 H21F 56.3 . . ? H21B C21 H21F 56.3 . . ? H21C C21 H21F 141.1 . . ? H21D C21 H21F 109.5 . . ? H21E C21 H21F 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C22 H22D 109.5 . . ? H22A C22 H22D 141.1 . . ? H22B C22 H22D 56.3 . . ? H22C C22 H22D 56.3 . . ? C17 C22 H22E 109.5 . . ? H22A C22 H22E 56.3 . . ? H22B C22 H22E 141.1 . . ? H22C C22 H22E 56.3 . . ? H22D C22 H22E 109.5 . . ? C17 C22 H22F 109.5 . . ? H22A C22 H22F 56.3 . . ? H22B C22 H22F 56.3 . . ? H22C C22 H22F 141.1 . . ? H22D C22 H22F 109.5 . . ? H22E C22 H22F 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 C14 N1 C1 C7 11.7(2) . . . . ? C2 N1 C1 C7 174.92(13) . . . . ? C14 N1 C1 N2 -171.62(11) . . . . ? C2 N1 C1 N2 -8.43(18) . . . . ? C5 N2 C1 C7 -0.94(14) . . . . ? C4 N2 C1 C7 179.02(11) . . . . ? C5 N2 C1 N1 -178.20(11) . . . . ? C4 N2 C1 N1 1.76(18) . . . . ? C1 N1 C2 C3 35.89(18) . . . . ? C14 N1 C2 C3 -160.93(12) . . . . ? N1 C2 C3 C4 -56.76(16) . . . . ? C1 N2 C4 C3 -23.21(17) . . . . ? C5 N2 C4 C3 156.74(12) . . . . ? C2 C3 C4 N2 50.25(16) . . . . ? C1 N2 C5 C8 -176.55(13) . . . . ? C4 N2 C5 C8 3.5(2) . . . . ? C1 N2 C5 C6 0.85(13) . . . . ? C4 N2 C5 C6 -179.11(12) . . . . ? N2 C5 C6 C11 -178.75(11) . . . . ? C8 C5 C6 C11 -1.05(18) . . . . ? N2 C5 C6 C7 -0.46(13) . . . . ? C8 C5 C6 C7 177.24(11) . . . . ? N1 C1 C7 C6 177.55(12) . . . . ? N2 C1 C7 C6 0.64(14) . . . . ? C11 C6 C7 C1 177.87(13) . . . . ? C5 C6 C7 C1 -0.11(14) . . . . ? N2 C5 C8 C9 177.86(12) . . . . ? C6 C5 C8 C9 0.79(18) . . . . ? N2 C5 C8 C12 -1.5(2) . . . . ? C6 C5 C8 C12 -178.59(13) . . . . ? C5 C8 C9 C10 -0.25(19) . . . . ? C12 C8 C9 C10 179.16(13) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C8 C9 C10 C13 -178.62(13) . . . . ? C9 C10 C11 C6 -0.21(19) . . . . ? C13 C10 C11 C6 178.36(12) . . . . ? C5 C6 C11 C10 0.73(18) . . . . ? C7 C6 C11 C10 -177.05(13) . . . . ? C1 N1 C14 C15 75.51(16) . . . . ? C2 N1 C14 C15 -87.97(15) . . . . ? C1 N1 C14 C19 -105.68(14) . . . . ? C2 N1 C14 C19 90.83(15) . . . . ? C19 C14 C15 C16 1.56(19) . . . . ? N1 C14 C15 C16 -179.67(11) . . . . ? C19 C14 C15 C21 -177.53(12) . . . . ? N1 C14 C15 C21 1.24(19) . . . . ? C14 C15 C16 C17 -1.25(19) . . . . ? C21 C15 C16 C17 177.85(13) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? C15 C16 C17 C22 179.10(13) . . . . ? C16 C17 C18 C19 1.9(2) . . . . ? C22 C17 C18 C19 -177.66(13) . . . . ? C17 C18 C19 C14 -1.56(19) . . . . ? C17 C18 C19 C20 176.98(13) . . . . ? C15 C14 C19 C18 -0.20(19) . . . . ? N1 C14 C19 C18 -179.00(11) . . . . ? C15 C14 C19 C20 -178.74(13) . . . . ? N1 C14 C19 C20 2.47(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.231 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.037 #===end data_k09mkw40 _database_code_depnum_ccdc_archive 'CCDC 776078' #TrackingRef 'bigcif.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H43 Br N2 Ni P' _chemical_formula_weight 721.35 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8540(1) _cell_length_b 17.1720(2) _cell_length_c 18.9610(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.454(1) _cell_angle_gamma 90.00 _cell_volume 3450.89(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 43949 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1500 _exptl_absorpt_coefficient_mu 1.797 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.494 _exptl_absorpt_correction_T_max 0.561 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 68858 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 30.01 _reflns_number_total 10058 _reflns_number_gt 6772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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. C3 disordered in 85:15 ratio over 2 sites. Only the major component was refined anisotropically. Hydrogens attached to C2 and C4 are included at positions based on the major component of C3. C2-C3, C3-C4, C2-C3a, C3a-C4 bond distances refined subject to similarity restraints. ; _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^)+(0.0339P)^2^+1.7823P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10058 _refine_ls_number_parameters 409 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Br1 Br 0.29752(2) -0.085988(13) 0.311773(13) 0.03071(7) Uani 1 1 d . . . Ni1 Ni 0.27995(3) 0.041315(16) 0.267731(14) 0.02135(7) Uani 1 1 d . . . P1 P 0.46798(5) 0.08351(3) 0.25653(3) 0.02174(12) Uani 1 1 d . . . N1 N 0.09353(18) 0.15269(11) 0.29133(10) 0.0265(4) Uani 1 1 d . B . N2 N 0.07719(18) 0.12202(11) 0.17204(10) 0.0265(4) Uani 1 1 d . B . C1 C 0.1395(2) 0.11324(12) 0.24112(12) 0.0228(4) Uani 1 1 d . . . C2 C -0.0184(2) 0.20420(15) 0.27536(14) 0.0392(6) Uani 1 1 d D . . H2A H 0.0087 0.2587 0.2707 0.047 Uiso 1 1 calc R A 1 H2B H -0.0633 0.2018 0.3155 0.047 Uiso 1 1 calc R A 1 C3 C -0.1062(3) 0.17883(17) 0.20562(15) 0.0333(6) Uiso 0.85 1 d PD B 1 H3A H -0.1449 0.1280 0.2128 0.040 Uiso 0.85 1 calc PR B 1 H3B H -0.1748 0.2175 0.1915 0.040 Uiso 0.85 1 calc PR B 1 C4 C -0.0343(3) 0.17193(17) 0.14776(14) 0.0424(7) Uani 1 1 d D . . H4A H -0.0889 0.1492 0.1040 0.051 Uiso 1 1 calc R B 1 H4B H -0.0072 0.2242 0.1353 0.051 Uiso 1 1 calc R B 1 C5 C 0.1556(2) 0.14454(12) 0.36647(12) 0.0252(5) Uani 1 1 d . . . C6 C 0.2443(2) 0.20039(13) 0.39767(12) 0.0281(5) Uani 1 1 d . B . C7 C 0.3018(2) 0.19157(14) 0.47012(13) 0.0316(5) Uani 1 1 d . . . H7 H 0.3635 0.2285 0.4920 0.038 Uiso 1 1 calc R B . C8 C 0.2722(2) 0.13051(15) 0.51180(13) 0.0328(5) Uani 1 1 d . B . C9 C 0.1812(2) 0.07744(14) 0.47831(13) 0.0318(5) Uani 1 1 d . . . H9 H 0.1593 0.0356 0.5060 0.038 Uiso 1 1 calc R B . C10 C 0.1214(2) 0.08317(13) 0.40621(13) 0.0280(5) Uani 1 1 d . B . C11 C 0.2778(3) 0.26764(14) 0.35457(14) 0.0376(6) Uani 1 1 d . . . H11A H 0.2710 0.2514 0.3043 0.056 Uiso 1 1 calc R B . H11B H 0.3645 0.2843 0.3751 0.056 Uiso 1 1 calc R . . H11C H 0.2199 0.3110 0.3562 0.056 Uiso 1 1 calc R . . C12 C 0.3377(3) 0.12109(17) 0.59003(14) 0.0466(7) Uani 1 1 d . . . H12A H 0.3064 0.1605 0.6192 0.070 Uiso 1 1 calc R B . H12B H 0.4289 0.1276 0.5950 0.070 Uiso 1 1 calc R . . H12C H 0.3203 0.0691 0.6068 0.070 Uiso 1 1 calc R . . C13 C 0.0233(3) 0.02435(14) 0.37245(15) 0.0382(6) Uani 1 1 d . . . H13A H 0.0097 -0.0127 0.4093 0.057 Uiso 1 1 calc R B . H13B H 0.0524 -0.0037 0.3341 0.057 Uiso 1 1 calc R . . H13C H -0.0560 0.0512 0.3520 0.057 Uiso 1 1 calc R . . C14 C 0.1245(2) 0.08098(13) 0.11687(11) 0.0244(5) Uani 1 1 d . . . C15 C 0.0984(2) 0.00177(13) 0.10562(11) 0.0247(5) Uani 1 1 d . B . C16 C 0.1507(2) -0.03660(13) 0.05403(12) 0.0278(5) Uani 1 1 d . . . H16 H 0.1340 -0.0905 0.0455 0.033 Uiso 1 1 calc R B . C17 C 0.2266(2) 0.00219(14) 0.01488(11) 0.0297(5) Uani 1 1 d . B . C18 C 0.2446(2) 0.08180(14) 0.02531(12) 0.0308(5) Uani 1 1 d . . . H18 H 0.2937 0.1091 -0.0025 0.037 Uiso 1 1 calc R B . C19 C 0.1931(2) 0.12253(13) 0.07503(12) 0.0283(5) Uani 1 1 d . B . C20 C 0.0175(2) -0.04317(14) 0.14716(13) 0.0314(5) Uani 1 1 d . . . H20A H 0.0716 -0.0686 0.1889 0.047 Uiso 1 1 calc R B . H20B H -0.0311 -0.0827 0.1157 0.047 Uiso 1 1 calc R . . H20C H -0.0405 -0.0073 0.1639 0.047 Uiso 1 1 calc R . . C21 C 0.2912(3) -0.04094(16) -0.03618(14) 0.0423(6) Uani 1 1 d . . . H21A H 0.2703 -0.0964 -0.0358 0.063 Uiso 1 1 calc R B . H21B H 0.3828 -0.0342 -0.0208 0.063 Uiso 1 1 calc R . . H21C H 0.2626 -0.0202 -0.0851 0.063 Uiso 1 1 calc R . . C22 C 0.2128(3) 0.20899(14) 0.08383(14) 0.0380(6) Uani 1 1 d . . . H22A H 0.2877 0.2242 0.0660 0.057 Uiso 1 1 calc R B . H22B H 0.2249 0.2227 0.1350 0.057 Uiso 1 1 calc R . . H22C H 0.1388 0.2364 0.0562 0.057 Uiso 1 1 calc R . . C23 C 0.5019(2) 0.16530(13) 0.20083(12) 0.0244(5) Uani 1 1 d . . . C24 C 0.4830(2) 0.24121(13) 0.22204(13) 0.0308(5) Uani 1 1 d . . . H24 H 0.4581 0.2498 0.2665 0.037 Uiso 1 1 calc R . . C25 C 0.4997(2) 0.30444(14) 0.17967(14) 0.0349(6) Uani 1 1 d . . . H25 H 0.4853 0.3557 0.1948 0.042 Uiso 1 1 calc R . . C26 C 0.5376(2) 0.29274(14) 0.11529(14) 0.0356(6) Uani 1 1 d . . . H26 H 0.5504 0.3359 0.0863 0.043 Uiso 1 1 calc R . . C27 C 0.5566(3) 0.21780(15) 0.09356(14) 0.0390(6) Uani 1 1 d . . . H27 H 0.5823 0.2095 0.0493 0.047 Uiso 1 1 calc R . . C28 C 0.5388(2) 0.15446(14) 0.13553(12) 0.0327(6) Uani 1 1 d . . . H28 H 0.5518 0.1032 0.1197 0.039 Uiso 1 1 calc R . . C29 C 0.5496(2) 0.00272(12) 0.22191(11) 0.0228(4) Uani 1 1 d . . . C30 C 0.4780(2) -0.04328(13) 0.16763(12) 0.0282(5) Uani 1 1 d . . . H30 H 0.3908 -0.0325 0.1506 0.034 Uiso 1 1 calc R . . C31 C 0.5335(3) -0.10482(14) 0.13828(14) 0.0361(6) Uani 1 1 d . . . H31 H 0.4846 -0.1350 0.1004 0.043 Uiso 1 1 calc R . . C32 C 0.6592(3) -0.12219(14) 0.16391(14) 0.0374(6) Uani 1 1 d . . . H32 H 0.6966 -0.1647 0.1442 0.045 Uiso 1 1 calc R . . C33 C 0.7306(3) -0.07748(15) 0.21852(14) 0.0365(6) Uani 1 1 d . . . H33 H 0.8170 -0.0896 0.2367 0.044 Uiso 1 1 calc R . . C34 C 0.6760(2) -0.01494(14) 0.24683(13) 0.0299(5) Uani 1 1 d . . . H34 H 0.7260 0.0161 0.2837 0.036 Uiso 1 1 calc R . . C35 C 0.5695(2) 0.10531(13) 0.34465(11) 0.0247(5) Uani 1 1 d . . . C36 C 0.5312(2) 0.07824(13) 0.40606(12) 0.0278(5) Uani 1 1 d . . . H36 H 0.4520 0.0528 0.4009 0.033 Uiso 1 1 calc R . . C37 C 0.6072(2) 0.08803(14) 0.47446(12) 0.0327(6) Uani 1 1 d . . . H37 H 0.5801 0.0691 0.5157 0.039 Uiso 1 1 calc R . . C38 C 0.7223(2) 0.12535(14) 0.48253(13) 0.0336(6) Uani 1 1 d . . . H38 H 0.7752 0.1311 0.5292 0.040 Uiso 1 1 calc R . . C39 C 0.7605(2) 0.15437(15) 0.42231(13) 0.0376(6) Uani 1 1 d . . . H39 H 0.8388 0.1809 0.4278 0.045 Uiso 1 1 calc R . . C40 C 0.6842(2) 0.14464(15) 0.35417(13) 0.0342(6) Uani 1 1 d . . . H40 H 0.7105 0.1651 0.3133 0.041 Uiso 1 1 calc R . . C3A C -0.0517(2) 0.23338(15) 0.20022(13) 0.093(9) Uiso 0.15 1 d PRD B 2 H3A1 H 0.0019 0.2788 0.1952 0.112 Uiso 0.15 1 calc PR C 2 H3A2 H -0.1408 0.2508 0.1892 0.112 Uiso 0.15 1 calc PR D 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 Br1 0.03330(14) 0.02401(11) 0.03439(13) 0.00543(9) 0.00637(10) -0.00112(10) Ni1 0.01937(15) 0.02118(14) 0.02402(14) 0.00099(11) 0.00586(11) 0.00117(11) P1 0.0208(3) 0.0232(3) 0.0220(3) 0.0002(2) 0.0061(2) 0.0007(2) N1 0.0225(10) 0.0267(10) 0.0303(10) -0.0048(8) 0.0055(8) 0.0044(8) N2 0.0245(11) 0.0276(10) 0.0258(10) -0.0005(8) 0.0017(8) 0.0061(8) C1 0.0207(12) 0.0206(10) 0.0277(11) -0.0018(9) 0.0068(9) -0.0041(8) C2 0.0322(15) 0.0364(14) 0.0509(16) -0.0059(12) 0.0132(12) 0.0110(11) C4 0.0335(15) 0.0480(16) 0.0409(15) -0.0009(12) -0.0022(12) 0.0184(12) C5 0.0251(12) 0.0251(11) 0.0276(11) -0.0063(9) 0.0109(9) 0.0015(9) C6 0.0282(13) 0.0259(11) 0.0325(12) -0.0074(10) 0.0117(10) -0.0004(10) C7 0.0305(14) 0.0299(12) 0.0355(13) -0.0107(10) 0.0099(11) -0.0021(10) C8 0.0338(14) 0.0359(13) 0.0306(12) -0.0043(10) 0.0113(11) 0.0081(11) C9 0.0382(15) 0.0279(12) 0.0347(13) 0.0012(10) 0.0195(11) 0.0047(11) C10 0.0273(13) 0.0238(11) 0.0367(13) -0.0056(10) 0.0151(10) 0.0005(9) C11 0.0418(16) 0.0320(13) 0.0415(15) -0.0051(11) 0.0145(12) -0.0079(11) C12 0.0567(19) 0.0509(17) 0.0320(14) -0.0017(13) 0.0088(13) 0.0113(14) C13 0.0380(16) 0.0315(13) 0.0479(15) -0.0070(11) 0.0155(13) -0.0062(11) C14 0.0228(12) 0.0281(11) 0.0196(10) 0.0011(9) -0.0011(9) 0.0025(9) C15 0.0227(12) 0.0273(11) 0.0218(10) 0.0029(9) -0.0006(9) 0.0009(9) C16 0.0322(13) 0.0236(11) 0.0248(11) -0.0011(9) -0.0003(10) -0.0003(10) C17 0.0333(14) 0.0341(12) 0.0201(11) 0.0000(10) 0.0021(9) 0.0020(11) C18 0.0332(14) 0.0359(13) 0.0230(11) 0.0063(10) 0.0054(10) -0.0044(11) C19 0.0286(13) 0.0261(11) 0.0268(12) 0.0029(9) -0.0016(10) -0.0016(10) C20 0.0312(14) 0.0294(12) 0.0343(13) 0.0033(10) 0.0082(11) -0.0034(10) C21 0.0480(17) 0.0481(16) 0.0332(14) -0.0039(12) 0.0141(12) 0.0032(13) C22 0.0367(15) 0.0285(12) 0.0466(15) 0.0034(11) 0.0039(12) -0.0033(11) C23 0.0193(11) 0.0260(11) 0.0278(11) 0.0017(9) 0.0050(9) -0.0007(9) C24 0.0324(14) 0.0290(12) 0.0331(13) -0.0028(10) 0.0116(11) -0.0009(10) C25 0.0304(14) 0.0241(12) 0.0492(15) -0.0011(11) 0.0064(12) -0.0014(10) C26 0.0297(14) 0.0317(13) 0.0462(15) 0.0116(11) 0.0101(12) -0.0001(10) C27 0.0472(17) 0.0378(14) 0.0373(14) 0.0084(11) 0.0212(13) 0.0040(12) C28 0.0395(15) 0.0299(12) 0.0326(13) 0.0033(10) 0.0160(11) 0.0044(11) C29 0.0233(12) 0.0239(10) 0.0231(10) 0.0038(9) 0.0090(9) 0.0004(9) C30 0.0278(13) 0.0291(12) 0.0284(12) 0.0000(10) 0.0073(10) 0.0025(10) C31 0.0446(17) 0.0301(13) 0.0375(14) -0.0048(11) 0.0173(12) -0.0026(11) C32 0.0482(17) 0.0239(12) 0.0484(15) 0.0048(11) 0.0286(13) 0.0066(11) C33 0.0291(14) 0.0397(14) 0.0445(15) 0.0132(12) 0.0164(12) 0.0119(11) C34 0.0259(13) 0.0324(12) 0.0321(12) 0.0037(10) 0.0079(10) 0.0023(10) C35 0.0255(13) 0.0261(11) 0.0221(11) -0.0019(9) 0.0042(9) 0.0031(9) C36 0.0297(13) 0.0264(11) 0.0279(12) -0.0012(9) 0.0078(10) -0.0014(10) C37 0.0423(16) 0.0314(12) 0.0245(12) -0.0010(10) 0.0073(11) 0.0028(11) C38 0.0391(15) 0.0304(12) 0.0282(12) -0.0073(10) 0.0002(11) 0.0035(11) C39 0.0312(14) 0.0439(15) 0.0359(14) -0.0072(12) 0.0029(11) -0.0075(12) C40 0.0318(14) 0.0429(14) 0.0287(12) -0.0028(11) 0.0080(11) -0.0061(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Ni1 2.3332(3) . ? Ni1 C1 1.942(2) . ? Ni1 P1 2.2187(6) . ? P1 C35 1.831(2) . ? P1 C23 1.841(2) . ? P1 C29 1.842(2) . ? N1 C1 1.349(3) . ? N1 C5 1.445(3) . ? N1 C2 1.480(3) . ? N2 C1 1.347(3) . ? N2 C14 1.445(3) . ? N2 C4 1.473(3) . ? C2 C3A 1.480(4) . ? C2 C3 1.518(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.482(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C3A 1.490(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.392(3) . ? C5 C6 1.396(3) . ? C6 C7 1.389(3) . ? C6 C11 1.504(3) . ? C7 C8 1.392(3) . ? C7 H7 0.9500 . ? C8 C9 1.392(4) . ? C8 C12 1.509(3) . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C13 1.507(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C19 1.395(3) . ? C14 C15 1.396(3) . ? C15 C16 1.397(3) . ? C15 C20 1.512(3) . ? C16 C17 1.392(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 C21 1.507(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9500 . ? C19 C22 1.504(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.392(3) . ? C23 C28 1.394(3) . ? C24 C25 1.386(3) . ? C24 H24 0.9500 . ? C25 C26 1.384(4) . ? C25 H25 0.9500 . ? C26 C27 1.380(4) . ? C26 H26 0.9500 . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.385(3) . ? C29 C30 1.394(3) . ? C30 C31 1.391(3) . ? C30 H30 0.9500 . ? C31 C32 1.379(4) . ? C31 H31 0.9500 . ? C32 C33 1.384(4) . ? C32 H32 0.9500 . ? C33 C34 1.389(3) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C40 1.393(3) . ? C35 C36 1.398(3) . ? C36 C37 1.389(3) . ? C36 H36 0.9500 . ? C37 C38 1.383(4) . ? C37 H37 0.9500 . ? C38 C39 1.389(4) . ? C38 H38 0.9500 . ? C39 C40 1.386(3) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? 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 Ni1 P1 117.02(6) . . ? C1 Ni1 Br1 133.45(6) . . ? P1 Ni1 Br1 109.536(19) . . ? C35 P1 C23 102.25(10) . . ? C35 P1 C29 103.77(10) . . ? C23 P1 C29 101.50(10) . . ? C35 P1 Ni1 111.38(8) . . ? C23 P1 Ni1 127.27(7) . . ? C29 P1 Ni1 108.13(7) . . ? C1 N1 C5 118.84(18) . . ? C1 N1 C2 124.6(2) . . ? C5 N1 C2 116.56(18) . . ? C1 N2 C14 117.87(18) . . ? C1 N2 C4 125.12(19) . . ? C14 N2 C4 117.00(18) . . ? N2 C1 N1 116.5(2) . . ? N2 C1 Ni1 121.67(15) . . ? N1 C1 Ni1 121.68(16) . . ? C3A C2 N1 114.8(2) . . ? C3A C2 C3 44.03(16) . . ? N1 C2 C3 109.9(2) . . ? C3A C2 H2A 67.1 . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C3A C2 H2B 134.1 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 109.6(2) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N2 C4 C3 110.1(2) . . ? N2 C4 C3A 114.7(2) . . ? C3 C4 C3A 44.45(16) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C3A C4 H4A 134.4 . . ? N2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? C3A C4 H4B 66.7 . . ? H4A C4 H4B 108.2 . . ? C10 C5 C6 122.0(2) . . ? C10 C5 N1 119.0(2) . . ? C6 C5 N1 118.9(2) . . ? C7 C6 C5 117.8(2) . . ? C7 C6 C11 120.7(2) . . ? C5 C6 C11 121.5(2) . . ? C6 C7 C8 122.3(2) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C7 C8 C9 117.5(2) . . ? C7 C8 C12 121.4(2) . . ? C9 C8 C12 121.0(2) . . ? C10 C9 C8 122.6(2) . . ? C10 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? C9 C10 C5 117.7(2) . . ? C9 C10 C13 120.6(2) . . ? C5 C10 C13 121.6(2) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 121.8(2) . . ? C19 C14 N2 118.6(2) . . ? C15 C14 N2 119.6(2) . . ? C14 C15 C16 117.8(2) . . ? C14 C15 C20 122.7(2) . . ? C16 C15 C20 119.6(2) . . ? C17 C16 C15 121.6(2) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 118.5(2) . . ? C18 C17 C21 120.3(2) . . ? C16 C17 C21 121.2(2) . . ? C19 C18 C17 121.9(2) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C14 118.2(2) . . ? C18 C19 C22 120.4(2) . . ? C14 C19 C22 121.5(2) . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 118.0(2) . . ? C24 C23 P1 119.24(17) . . ? C28 C23 P1 122.61(17) . . ? C25 C24 C23 121.3(2) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 C24 119.9(2) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 119.4(2) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 120.8(2) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C28 C23 120.5(2) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? C34 C29 C30 118.8(2) . . ? C34 C29 P1 124.10(17) . . ? C30 C29 P1 117.10(17) . . ? C31 C30 C29 120.4(2) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C32 C31 C30 120.3(2) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C33 119.7(2) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C32 C33 C34 120.1(2) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C29 C34 C33 120.7(2) . . ? C29 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C40 C35 C36 118.1(2) . . ? C40 C35 P1 124.22(17) . . ? C36 C35 P1 117.60(17) . . ? C37 C36 C35 120.9(2) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C38 C37 C36 120.0(2) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C38 C39 119.9(2) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C40 C39 C38 119.9(2) . . ? C40 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? C39 C40 C35 121.1(2) . . ? C39 C40 H40 119.4 . . ? C35 C40 H40 119.4 . . ? C2 C3A C4 111.3(2) . . ? C2 C3A H3A1 109.4 . . ? C4 C3A H3A1 109.4 . . ? C2 C3A H3A2 109.4 . . ? C4 C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108.0 . . ? 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 C1 Ni1 P1 C35 105.80(10) . . . . ? Br1 Ni1 P1 C35 -73.88(8) . . . . ? C1 Ni1 P1 C23 -19.95(12) . . . . ? Br1 Ni1 P1 C23 160.37(9) . . . . ? C1 Ni1 P1 C29 -140.80(10) . . . . ? Br1 Ni1 P1 C29 39.53(7) . . . . ? C14 N2 C1 N1 179.55(19) . . . . ? C4 N2 C1 N1 1.1(3) . . . . ? C14 N2 C1 Ni1 -5.1(3) . . . . ? C4 N2 C1 Ni1 176.50(19) . . . . ? C5 N1 C1 N2 179.13(19) . . . . ? C2 N1 C1 N2 -0.3(3) . . . . ? C5 N1 C1 Ni1 3.8(3) . . . . ? C2 N1 C1 Ni1 -175.67(18) . . . . ? P1 Ni1 C1 N2 83.25(18) . . . . ? Br1 Ni1 C1 N2 -97.17(18) . . . . ? P1 Ni1 C1 N1 -101.62(17) . . . . ? Br1 Ni1 C1 N1 77.96(19) . . . . ? C1 N1 C2 C3A -21.3(3) . . . . ? C5 N1 C2 C3A 159.3(2) . . . . ? C1 N1 C2 C3 26.3(3) . . . . ? C5 N1 C2 C3 -153.2(2) . . . . ? C3A C2 C3 C4 53.9(2) . . . . ? N1 C2 C3 C4 -51.6(3) . . . . ? C1 N2 C4 C3 -28.6(3) . . . . ? C14 N2 C4 C3 153.0(2) . . . . ? C1 N2 C4 C3A 19.5(4) . . . . ? C14 N2 C4 C3A -159.0(2) . . . . ? C2 C3 C4 N2 52.4(3) . . . . ? C2 C3 C4 C3A -52.8(2) . . . . ? C1 N1 C5 C10 -86.3(3) . . . . ? C2 N1 C5 C10 93.2(2) . . . . ? C1 N1 C5 C6 96.4(2) . . . . ? C2 N1 C5 C6 -84.2(3) . . . . ? C10 C5 C6 C7 2.2(3) . . . . ? N1 C5 C6 C7 179.5(2) . . . . ? C10 C5 C6 C11 -178.3(2) . . . . ? N1 C5 C6 C11 -1.1(3) . . . . ? C5 C6 C7 C8 -1.2(3) . . . . ? C11 C6 C7 C8 179.4(2) . . . . ? C6 C7 C8 C9 -0.1(3) . . . . ? C6 C7 C8 C12 178.8(2) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C12 C8 C9 C10 -178.4(2) . . . . ? C8 C9 C10 C5 0.4(3) . . . . ? C8 C9 C10 C13 -179.9(2) . . . . ? C6 C5 C10 C9 -1.8(3) . . . . ? N1 C5 C10 C9 -179.12(19) . . . . ? C6 C5 C10 C13 178.5(2) . . . . ? N1 C5 C10 C13 1.2(3) . . . . ? C1 N2 C14 C19 -102.6(2) . . . . ? C4 N2 C14 C19 76.0(3) . . . . ? C1 N2 C14 C15 78.9(3) . . . . ? C4 N2 C14 C15 -102.6(3) . . . . ? C19 C14 C15 C16 4.4(3) . . . . ? N2 C14 C15 C16 -177.13(19) . . . . ? C19 C14 C15 C20 -176.1(2) . . . . ? N2 C14 C15 C20 2.4(3) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C20 C15 C16 C17 -179.5(2) . . . . ? C15 C16 C17 C18 -3.3(3) . . . . ? C15 C16 C17 C21 174.9(2) . . . . ? C16 C17 C18 C19 2.3(4) . . . . ? C21 C17 C18 C19 -175.9(2) . . . . ? C17 C18 C19 C14 1.9(4) . . . . ? C17 C18 C19 C22 -178.9(2) . . . . ? C15 C14 C19 C18 -5.3(3) . . . . ? N2 C14 C19 C18 176.1(2) . . . . ? C15 C14 C19 C22 175.5(2) . . . . ? N2 C14 C19 C22 -3.0(3) . . . . ? C35 P1 C23 C24 -57.2(2) . . . . ? C29 P1 C23 C24 -164.26(19) . . . . ? Ni1 P1 C23 C24 72.1(2) . . . . ? C35 P1 C23 C28 126.7(2) . . . . ? C29 P1 C23 C28 19.7(2) . . . . ? Ni1 P1 C23 C28 -104.0(2) . . . . ? C28 C23 C24 C25 0.2(4) . . . . ? P1 C23 C24 C25 -176.02(19) . . . . ? C23 C24 C25 C26 -0.9(4) . . . . ? C24 C25 C26 C27 0.9(4) . . . . ? C25 C26 C27 C28 -0.3(4) . . . . ? C26 C27 C28 C23 -0.4(4) . . . . ? C24 C23 C28 C27 0.4(4) . . . . ? P1 C23 C28 C27 176.5(2) . . . . ? C35 P1 C29 C34 -19.7(2) . . . . ? C23 P1 C29 C34 86.1(2) . . . . ? Ni1 P1 C29 C34 -138.07(17) . . . . ? C35 P1 C29 C30 159.80(17) . . . . ? C23 P1 C29 C30 -94.37(18) . . . . ? Ni1 P1 C29 C30 41.43(17) . . . . ? C34 C29 C30 C31 -1.2(3) . . . . ? P1 C29 C30 C31 179.30(17) . . . . ? C29 C30 C31 C32 1.7(3) . . . . ? C30 C31 C32 C33 -0.8(4) . . . . ? C31 C32 C33 C34 -0.6(4) . . . . ? C30 C29 C34 C33 -0.2(3) . . . . ? P1 C29 C34 C33 179.27(17) . . . . ? C32 C33 C34 C29 1.1(3) . . . . ? C23 P1 C35 C40 -30.2(2) . . . . ? C29 P1 C35 C40 75.0(2) . . . . ? Ni1 P1 C35 C40 -168.85(18) . . . . ? C23 P1 C35 C36 152.07(18) . . . . ? C29 P1 C35 C36 -102.66(18) . . . . ? Ni1 P1 C35 C36 13.44(19) . . . . ? C40 C35 C36 C37 -2.1(3) . . . . ? P1 C35 C36 C37 175.75(18) . . . . ? C35 C36 C37 C38 0.3(3) . . . . ? C36 C37 C38 C39 1.3(4) . . . . ? C37 C38 C39 C40 -1.1(4) . . . . ? C38 C39 C40 C35 -0.7(4) . . . . ? C36 C35 C40 C39 2.3(4) . . . . ? P1 C35 C40 C39 -175.4(2) . . . . ? N1 C2 C3A C4 39.2(3) . . . . ? C3 C2 C3A C4 -54.4(2) . . . . ? N2 C4 C3A C2 -38.4(3) . . . . ? C3 C4 C3A C2 55.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.613 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.080