# 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_cm_30_08 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C28 H31 N2 Ni O2' _chemical_formula_sum 'C28 H31 N2 Ni O2' _chemical_compound_source synthesys _exptl_crystal_recrystallization_method 'dichloromethane, ethanol' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour green _diffrn_ambient_temperature 296(2) _chemical_formula_weight 486.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_int_tables_number 14 _chemical_absolute_configuration unk _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 19.4933(18) _cell_length_b 6.1948(6) _cell_length_c 20.415(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.986(9) _cell_angle_gamma 90.00 _cell_volume 2447.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.0648 _cell_measurement_theta_max 28.6299 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 0.820 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10057 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_unetI/netI 0.0954 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4806 _reflns_number_gt 3042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+7.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4806 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1117 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.1560 _refine_ls_wR_factor_gt 0.1306 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.75552(3) 0.58837(11) 0.67431(3) 0.0416(2) Uani 1 1 d . . . O1 O 0.80006(17) 0.8085(6) 0.72442(18) 0.0497(10) Uani 1 1 d . . . O2 O 0.82544(18) 0.6053(6) 0.62155(18) 0.0498(10) Uani 1 1 d . . . N1 N 0.68233(19) 0.6421(7) 0.7234(2) 0.0389(10) Uani 1 1 d . . . N2 N 0.7206(2) 0.3255(7) 0.6412(2) 0.0443(11) Uani 1 1 d . . . C7 C 0.6142(2) 0.5826(9) 0.7002(2) 0.0383(12) Uani 1 1 d . . . C12 C 0.6037(3) 0.3793(9) 0.6720(2) 0.0436(13) Uani 1 1 d . . . C20 C 0.8393(3) 0.4683(9) 0.5770(3) 0.0459(13) Uani 1 1 d . . . C3 C 0.7945(3) 1.0196(9) 0.8229(3) 0.0444(13) Uani 1 1 d . . . C1 C 0.6997(2) 0.7857(8) 0.7733(2) 0.0376(12) Uani 1 1 d . . . C15 C 0.8053(3) 0.2660(9) 0.5655(3) 0.0427(13) Uani 1 1 d . . . C6 C 0.6583(3) 0.8540(8) 0.8214(2) 0.0426(13) Uani 1 1 d . . . H6 H 0.6143 0.7961 0.8218 0.051 Uiso 1 1 calc R . . C25 C 0.6378(3) 1.0975(9) 0.9170(3) 0.0500(14) Uani 1 1 d . . . C14 C 0.7484(3) 0.2061(9) 0.6001(3) 0.0463(14) Uani 1 1 d . . . H14 H 0.7299 0.0689 0.5920 0.056 Uiso 1 1 calc R . . C5 C 0.6822(3) 1.0043(9) 0.8674(3) 0.0428(13) Uani 1 1 d . . . C2 C 0.7686(3) 0.8721(8) 0.7732(3) 0.0415(12) Uani 1 1 d . . . C9 C 0.4939(3) 0.6618(11) 0.6725(3) 0.0566(16) Uani 1 1 d . . . H9 H 0.4566 0.7552 0.6729 0.068 Uiso 1 1 calc R . . C4 C 0.7504(3) 1.0829(9) 0.8667(3) 0.0469(14) Uani 1 1 d . . . H4 H 0.7665 1.1849 0.8983 0.056 Uiso 1 1 calc R . . C21 C 0.8690(3) 1.1002(10) 0.8261(3) 0.0512(15) Uani 1 1 d . . . C10 C 0.4836(3) 0.4612(12) 0.6445(3) 0.0630(18) Uani 1 1 d . . . H10 H 0.4398 0.4211 0.6252 0.076 Uiso 1 1 calc R . . C17 C 0.8786(3) 0.1789(11) 0.4816(3) 0.0623(18) Uani 1 1 d . . . H17 H 0.8923 0.0845 0.4502 0.075 Uiso 1 1 calc R . . C19 C 0.8924(3) 0.5192(10) 0.5379(3) 0.0525(15) Uani 1 1 d . . . H19 H 0.9154 0.6507 0.5436 0.063 Uiso 1 1 calc R . . C18 C 0.9098(3) 0.3766(11) 0.4922(3) 0.0564(16) Uani 1 1 d . . . H18 H 0.9445 0.4146 0.4669 0.068 Uiso 1 1 calc R . . C11 C 0.5379(3) 0.3195(11) 0.6449(3) 0.0575(16) Uani 1 1 d . . . H11 H 0.5303 0.1824 0.6269 0.069 Uiso 1 1 calc R . . C8 C 0.5585(3) 0.7272(10) 0.7001(3) 0.0470(14) Uani 1 1 d . . . H8 H 0.5652 0.8642 0.7183 0.056 Uiso 1 1 calc R . . C16 C 0.8268(3) 0.1236(10) 0.5183(3) 0.0571(16) Uani 1 1 d . . . H16 H 0.8055 -0.0103 0.5119 0.069 Uiso 1 1 calc R . . C13 C 0.6631(3) 0.2253(9) 0.6719(3) 0.0535(15) Uani 1 1 d . . . H13A H 0.6794 0.1836 0.7169 0.064 Uiso 1 1 calc R . . H13B H 0.6476 0.0961 0.6476 0.064 Uiso 1 1 calc R . . C23 C 0.8786(3) 1.2289(11) 0.7641(3) 0.0685(18) Uani 1 1 d . . . H23A H 0.8483 1.3517 0.7609 0.103 Uiso 1 1 calc R . . H23B H 0.8678 1.1390 0.7259 0.103 Uiso 1 1 calc R . . H23C H 0.9256 1.2770 0.7664 0.103 Uiso 1 1 calc R . . C22 C 0.9180(3) 0.9067(11) 0.8322(3) 0.0706(19) Uani 1 1 d . . . H22A H 0.9646 0.9557 0.8313 0.106 Uiso 1 1 calc R . . H22B H 0.9057 0.8097 0.7960 0.106 Uiso 1 1 calc R . . H22C H 0.9145 0.8331 0.8730 0.106 Uiso 1 1 calc R . . C24 C 0.8881(3) 1.2443(13) 0.8860(3) 0.088(2) Uani 1 1 d . . . H24A H 0.9364 1.2800 0.8893 0.132 Uiso 1 1 calc R . . H24B H 0.8789 1.1695 0.9252 0.132 Uiso 1 1 calc R . . H24C H 0.8612 1.3743 0.8813 0.132 Uiso 1 1 calc R . . C28 C 0.5727(3) 0.9684(12) 0.9206(4) 0.087(2) Uani 1 1 d . . . H28A H 0.5484 1.0250 0.9550 0.131 Uiso 1 1 calc R . . H28B H 0.5845 0.8201 0.9298 0.131 Uiso 1 1 calc R . . H28C H 0.5437 0.9779 0.8792 0.131 Uiso 1 1 calc R . . C27 C 0.6768(4) 1.1008(14) 0.9865(3) 0.095(3) Uani 1 1 d . . . H27A H 0.6495 1.1740 1.0158 0.142 Uiso 1 1 calc R . . H27B H 0.7199 1.1750 0.9860 0.142 Uiso 1 1 calc R . . H27C H 0.6854 0.9554 1.0016 0.142 Uiso 1 1 calc R . . C26 C 0.6189(5) 1.3267(11) 0.8967(4) 0.110(3) Uani 1 1 d . . . H26A H 0.5935 1.3266 0.8534 0.165 Uiso 1 1 calc R . . H26B H 0.6603 1.4105 0.8964 0.165 Uiso 1 1 calc R . . H26C H 0.5910 1.3886 0.9275 0.165 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 0.0336(4) 0.0418(4) 0.0491(4) -0.0058(3) 0.0034(3) -0.0051(3) O1 0.041(2) 0.053(2) 0.055(2) -0.018(2) 0.0037(18) -0.0013(18) O2 0.041(2) 0.051(2) 0.059(2) -0.010(2) 0.0154(18) -0.0100(18) N1 0.026(2) 0.043(3) 0.048(2) -0.003(2) 0.0092(18) -0.0057(19) N2 0.039(2) 0.037(3) 0.056(3) -0.003(2) -0.001(2) 0.002(2) C7 0.029(2) 0.049(3) 0.038(3) 0.005(3) 0.005(2) -0.008(2) C12 0.036(3) 0.055(4) 0.040(3) 0.007(3) 0.004(2) -0.012(3) C20 0.043(3) 0.046(3) 0.046(3) -0.008(3) -0.008(2) 0.003(3) C3 0.039(3) 0.046(3) 0.048(3) -0.007(3) 0.006(2) -0.007(2) C1 0.033(3) 0.037(3) 0.043(3) 0.001(3) 0.004(2) 0.004(2) C15 0.034(3) 0.043(3) 0.049(3) -0.001(3) -0.006(2) -0.003(2) C6 0.033(3) 0.046(3) 0.049(3) 0.006(3) 0.005(2) 0.003(2) C25 0.048(3) 0.049(3) 0.055(3) 0.000(3) 0.014(3) 0.002(3) C14 0.040(3) 0.039(3) 0.056(3) -0.006(3) -0.008(3) -0.008(2) C5 0.037(3) 0.046(3) 0.047(3) 0.001(3) 0.012(2) 0.004(2) C2 0.038(3) 0.037(3) 0.048(3) -0.002(3) 0.001(2) -0.002(2) C9 0.036(3) 0.083(5) 0.051(3) 0.011(4) 0.006(3) 0.002(3) C4 0.039(3) 0.051(3) 0.051(3) -0.011(3) 0.007(2) -0.003(3) C21 0.037(3) 0.061(4) 0.056(3) -0.017(3) 0.007(3) -0.009(3) C10 0.030(3) 0.096(5) 0.062(4) 0.006(4) -0.001(3) -0.017(3) C17 0.050(4) 0.080(5) 0.056(4) -0.026(4) 0.006(3) 0.000(3) C19 0.042(3) 0.057(4) 0.058(3) -0.005(3) 0.002(3) -0.003(3) C18 0.043(3) 0.081(5) 0.045(3) -0.008(3) 0.003(3) 0.005(3) C11 0.049(3) 0.067(4) 0.056(4) 0.004(3) 0.004(3) -0.022(3) C8 0.037(3) 0.056(4) 0.048(3) 0.008(3) 0.002(2) -0.001(3) C16 0.049(3) 0.057(4) 0.062(4) -0.019(3) -0.005(3) -0.001(3) C13 0.052(3) 0.044(3) 0.067(4) 0.005(3) 0.017(3) -0.012(3) C23 0.053(4) 0.065(4) 0.088(5) -0.003(4) 0.009(3) -0.011(3) C22 0.039(3) 0.087(5) 0.085(5) -0.009(4) 0.003(3) -0.011(3) C24 0.050(4) 0.122(7) 0.093(5) -0.048(5) 0.015(4) -0.029(4) C28 0.072(5) 0.093(6) 0.105(6) -0.026(5) 0.040(4) -0.011(4) C27 0.078(5) 0.145(8) 0.064(4) -0.011(5) 0.021(4) -0.001(5) C26 0.138(8) 0.067(5) 0.140(8) 0.018(5) 0.074(6) 0.043(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 O2 1.840(4) . ? Ni1 O1 1.856(4) . ? Ni1 N2 1.860(4) . ? Ni1 N1 1.870(4) . ? O1 C2 1.293(6) . ? O2 C20 1.296(6) . ? N1 C1 1.363(6) . ? N1 C7 1.404(6) . ? N2 C14 1.286(6) . ? N2 C13 1.486(6) . ? C7 C12 1.390(7) . ? C7 C8 1.408(7) . ? C12 C11 1.385(7) . ? C12 C13 1.500(7) . ? C20 C19 1.418(7) . ? C20 C15 1.423(7) . ? C3 C4 1.370(7) . ? C3 C2 1.413(7) . ? C3 C21 1.530(7) . ? C1 C6 1.410(7) . ? C1 C2 1.447(7) . ? C15 C16 1.406(7) . ? C15 C14 1.436(7) . ? C6 C5 1.363(7) . ? C25 C28 1.509(8) . ? C25 C26 1.512(8) . ? C25 C5 1.525(7) . ? C25 C27 1.526(8) . ? C5 C4 1.417(7) . ? C9 C10 1.373(9) . ? C9 C8 1.376(7) . ? C21 C24 1.524(8) . ? C21 C23 1.527(8) . ? C21 C22 1.528(8) . ? C10 C11 1.374(8) . ? C17 C18 1.373(8) . ? C17 C16 1.373(8) . ? C19 C18 1.358(8) . ? 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 O2 Ni1 O1 87.17(16) . . ? O2 Ni1 N2 95.80(19) . . ? O1 Ni1 N2 165.83(18) . . ? O2 Ni1 N1 166.19(18) . . ? O1 Ni1 N1 84.84(17) . . ? N2 Ni1 N1 94.69(19) . . ? C2 O1 Ni1 114.5(3) . . ? C20 O2 Ni1 127.3(4) . . ? C1 N1 C7 124.2(4) . . ? C1 N1 Ni1 112.4(3) . . ? C7 N1 Ni1 121.6(3) . . ? C14 N2 C13 115.7(5) . . ? C14 N2 Ni1 125.2(4) . . ? C13 N2 Ni1 118.3(4) . . ? C12 C7 N1 117.6(5) . . ? C12 C7 C8 120.1(5) . . ? N1 C7 C8 122.1(5) . . ? C11 C12 C7 119.4(5) . . ? C11 C12 C13 120.5(5) . . ? C7 C12 C13 120.1(4) . . ? O2 C20 C19 118.6(5) . . ? O2 C20 C15 124.1(5) . . ? C19 C20 C15 117.3(5) . . ? C4 C3 C2 117.2(5) . . ? C4 C3 C21 123.1(5) . . ? C2 C3 C21 119.7(5) . . ? N1 C1 C6 127.3(4) . . ? N1 C1 C2 112.7(4) . . ? C6 C1 C2 120.0(5) . . ? C16 C15 C20 119.7(5) . . ? C16 C15 C14 119.1(5) . . ? C20 C15 C14 121.2(5) . . ? C5 C6 C1 120.5(5) . . ? C28 C25 C26 109.5(6) . . ? C28 C25 C5 112.4(5) . . ? C26 C25 C5 108.2(5) . . ? C28 C25 C27 106.8(5) . . ? C26 C25 C27 108.6(6) . . ? C5 C25 C27 111.3(5) . . ? N2 C14 C15 125.7(5) . . ? C6 C5 C4 118.1(5) . . ? C6 C5 C25 122.8(5) . . ? C4 C5 C25 119.1(5) . . ? O1 C2 C3 126.1(5) . . ? O1 C2 C1 114.6(4) . . ? C3 C2 C1 119.3(5) . . ? C10 C9 C8 121.1(6) . . ? C3 C4 C5 124.8(5) . . ? C24 C21 C23 108.5(5) . . ? C24 C21 C22 107.8(5) . . ? C23 C21 C22 109.8(5) . . ? C24 C21 C3 111.3(5) . . ? C23 C21 C3 110.3(5) . . ? C22 C21 C3 109.2(5) . . ? C9 C10 C11 120.2(5) . . ? C18 C17 C16 118.5(6) . . ? C18 C19 C20 120.2(6) . . ? C19 C18 C17 123.1(6) . . ? C10 C11 C12 120.5(6) . . ? C9 C8 C7 118.8(6) . . ? C17 C16 C15 121.1(6) . . ? N2 C13 C12 110.9(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.932 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 951779' ####################################################################### # # 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_sg_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H47 N2 Ni O2' _chemical_formula_sum 'C36 H47 N2 Ni O2' _chemical_compound_source synthesis _chemical_properties_physical ' paramagnetic, oxygen-sensitive' _exptl_crystal_recrystallization_method 'dichloromethane, acetonitrile' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour green _diffrn_ambient_temperature 296(2) _chemical_formula_weight 598.47 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 monoclinic _symmetry_space_group_name_H-M 'C1 2/c1' _symmetry_int_tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' _chemical_absolute_configuration ? 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 28.2555(10) _cell_length_b 13.6775(4) _cell_length_c 19.3826(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.585(2) _cell_angle_gamma 90.00 _cell_volume 6811.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2568 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.735 _exptl_absorpt_correction_T_max 0.796 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29563 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5871 _reflns_number_gt 4574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5871 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.153736(11) 0.343037(19) 0.481341(15) 0.03473(13) Uani 1 1 d . . . C18 C 0.16716(9) 0.06090(16) 0.31006(12) 0.0398(5) Uani 1 1 d . . . H18 H 0.1529 0.0041 0.2831 0.048 Uiso 1 1 calc R . . C15 C 0.20670(8) 0.23350(15) 0.38416(11) 0.0341(5) Uani 1 1 d . . . C7 C 0.15198(9) 0.55327(16) 0.47734(12) 0.0391(5) Uani 1 1 d . . . C4 C 0.06421(9) 0.43787(17) 0.64480(13) 0.0432(6) Uani 1 1 d . . . H4 H 0.0461 0.4297 0.6750 0.052 Uiso 1 1 calc R . . C2 C 0.09858(9) 0.37180(16) 0.56215(12) 0.0384(5) Uani 1 1 d . . . C20 C 0.16722(8) 0.18543(15) 0.39744(11) 0.0338(5) Uani 1 1 d . . . C17 C 0.20919(9) 0.10422(16) 0.30000(12) 0.0394(5) Uani 1 1 d . . . C3 C 0.07181(9) 0.35637(16) 0.60967(13) 0.0392(5) Uani 1 1 d . . . C14 C 0.22707(9) 0.32605(15) 0.41893(12) 0.0368(5) Uani 1 1 d . . . H14 H 0.2568 0.3492 0.4149 0.044 Uiso 1 1 calc R . . C1 C 0.11545(8) 0.46762(15) 0.55389(12) 0.0367(5) Uani 1 1 d . . . C19 C 0.14574(8) 0.09727(15) 0.35746(12) 0.0349(5) Uani 1 1 d . . . C16 C 0.22793(9) 0.19006(16) 0.33712(12) 0.0385(5) Uani 1 1 d . . . H16 H 0.2554 0.2209 0.3313 0.046 Uiso 1 1 calc R . . C13 C 0.23467(8) 0.47250(15) 0.48928(13) 0.0408(5) Uani 1 1 d . . . H13A H 0.2623 0.4836 0.4729 0.049 Uiso 1 1 calc R . . H13B H 0.2504 0.4669 0.5441 0.049 Uiso 1 1 calc R . . C12 C 0.19790(9) 0.55784(15) 0.46616(12) 0.0393(5) Uani 1 1 d . . . C5 C 0.08146(9) 0.53341(17) 0.63917(13) 0.0424(6) Uani 1 1 d . . . C11 C 0.20863(11) 0.64112(17) 0.43499(15) 0.0533(7) Uani 1 1 d . . . H11 H 0.2393 0.6446 0.4282 0.064 Uiso 1 1 calc R . . C6 C 0.10683(9) 0.54804(16) 0.59311(13) 0.0418(5) Uani 1 1 d . . . H6 H 0.1182 0.6102 0.5877 0.050 Uiso 1 1 calc R . . C10 C 0.17456(13) 0.71953(19) 0.41363(17) 0.0712(9) Uani 1 1 d . . . H10 H 0.1826 0.7760 0.3940 0.085 Uiso 1 1 calc R . . C8 C 0.11668(10) 0.63127(18) 0.45269(15) 0.0524(7) Uani 1 1 d . . . H8 H 0.0852 0.6277 0.4573 0.063 Uiso 1 1 calc R . . C9 C 0.12847(13) 0.71281(19) 0.42186(17) 0.0680(8) Uani 1 1 d . . . H9 H 0.1050 0.7645 0.4062 0.082 Uiso 1 1 calc R . . C21 C 0.23072(10) 0.05425(19) 0.24789(14) 0.0504(6) Uani 1 1 d . . . C22 C 0.27910(11) 0.1069(2) 0.24959(17) 0.0664(8) Uani 1 1 d . . . H22A H 0.2699 0.1719 0.2301 0.100 Uiso 1 1 calc R . . H22B H 0.2926 0.0717 0.2189 0.100 Uiso 1 1 calc R . . H22C H 0.3051 0.1099 0.3009 0.100 Uiso 1 1 calc R . . C23 C 0.24617(12) -0.0519(2) 0.27445(19) 0.0751(9) Uani 1 1 d . . . H23A H 0.2719 -0.0519 0.3260 0.113 Uiso 1 1 calc R . . H23B H 0.2602 -0.0827 0.2425 0.113 Uiso 1 1 calc R . . H23C H 0.2160 -0.0873 0.2714 0.113 Uiso 1 1 calc R . . C24 C 0.18905(12) 0.0542(3) 0.16650(15) 0.0754(9) Uani 1 1 d . . . H24A H 0.1580 0.0237 0.1650 0.113 Uiso 1 1 calc R . . H24B H 0.2015 0.0186 0.1347 0.113 Uiso 1 1 calc R . . H24C H 0.1814 0.1203 0.1486 0.113 Uiso 1 1 calc R . . C25 C 0.09971(9) 0.04694(16) 0.36675(13) 0.0407(5) Uani 1 1 d . . . C26 C 0.07869(10) -0.03862(18) 0.31149(15) 0.0563(7) Uani 1 1 d . . . H26A H 0.0668 -0.0151 0.2604 0.084 Uiso 1 1 calc R . . H26B H 0.0502 -0.0686 0.3184 0.084 Uiso 1 1 calc R . . H26C H 0.1058 -0.0859 0.3211 0.084 Uiso 1 1 calc R . . C27 C 0.11757(10) 0.0074(2) 0.44791(14) 0.0565(7) Uani 1 1 d . . . H27A H 0.1461 -0.0368 0.4587 0.085 Uiso 1 1 calc R . . H27B H 0.0893 -0.0264 0.4525 0.085 Uiso 1 1 calc R . . H27C H 0.1284 0.0608 0.4832 0.085 Uiso 1 1 calc R . . C28 C 0.05501(9) 0.12014(19) 0.34991(16) 0.0564(7) Uani 1 1 d . . . H28A H 0.0652 0.1687 0.3892 0.085 Uiso 1 1 calc R . . H28B H 0.0248 0.0862 0.3481 0.085 Uiso 1 1 calc R . . H28C H 0.0471 0.1512 0.3020 0.085 Uiso 1 1 calc R . . C29 C 0.05507(10) 0.25332(18) 0.62112(14) 0.0488(6) Uani 1 1 d . . . C30 C 0.10309(12) 0.1866(2) 0.65411(19) 0.0746(9) Uani 1 1 d . . . H30A H 0.0923 0.1211 0.6583 0.112 Uiso 1 1 calc R . . H30B H 0.1262 0.2098 0.7034 0.112 Uiso 1 1 calc R . . H30C H 0.1208 0.1871 0.6212 0.112 Uiso 1 1 calc R . . C32 C 0.02921(11) 0.2532(2) 0.67670(16) 0.0659(8) Uani 1 1 d . . . H32A H -0.0010 0.2944 0.6574 0.099 Uiso 1 1 calc R . . H32B H 0.0533 0.2774 0.7251 0.099 Uiso 1 1 calc R . . H32C H 0.0191 0.1877 0.6824 0.099 Uiso 1 1 calc R . . C31 C 0.01587(12) 0.2128(2) 0.54483(17) 0.0744(9) Uani 1 1 d . . . H31A H -0.0146 0.2534 0.5259 0.112 Uiso 1 1 calc R . . H31B H 0.0064 0.1474 0.5518 0.112 Uiso 1 1 calc R . . H31C H 0.0314 0.2125 0.5091 0.112 Uiso 1 1 calc R . . C33 C 0.07163(10) 0.61655(19) 0.68504(14) 0.0519(6) Uani 1 1 d . . . C36 C 0.09543(14) 0.7132(2) 0.67603(18) 0.0779(9) Uani 1 1 d . . . H36A H 0.1322 0.7050 0.6917 0.117 Uiso 1 1 calc R . . H36B H 0.0894 0.7622 0.7069 0.117 Uiso 1 1 calc R . . H36C H 0.0796 0.7331 0.6238 0.117 Uiso 1 1 calc R . . C34 C 0.01262(12) 0.6294(2) 0.65803(18) 0.0724(9) Uani 1 1 d . . . H34A H -0.0029 0.6427 0.6046 0.109 Uiso 1 1 calc R . . H34B H 0.0059 0.6829 0.6847 0.109 Uiso 1 1 calc R . . H34C H -0.0020 0.5706 0.6679 0.109 Uiso 1 1 calc R . . C35 C 0.09618(13) 0.5892(2) 0.76974(15) 0.0734(9) Uani 1 1 d . . . H35A H 0.0807 0.5299 0.7771 0.110 Uiso 1 1 calc R . . H35B H 0.0902 0.6409 0.7987 0.110 Uiso 1 1 calc R . . H35C H 0.1329 0.5798 0.7863 0.110 Uiso 1 1 calc R . . O1 O 0.10973(6) 0.30196(11) 0.52512(9) 0.0435(4) Uani 1 1 d . . . O2 O 0.15033(6) 0.21836(10) 0.44703(8) 0.0410(4) Uani 1 1 d . . . N1 N 0.14225(7) 0.46800(12) 0.50897(10) 0.0367(4) Uani 1 1 d . . . N2 N 0.20724(7) 0.38004(12) 0.45555(10) 0.0340(4) 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 Ni1 0.0432(2) 0.03120(18) 0.03682(19) -0.00205(11) 0.02358(15) -0.00190(12) C18 0.0445(14) 0.0368(12) 0.0383(12) -0.0053(9) 0.0175(11) 0.0019(10) C15 0.0365(13) 0.0349(11) 0.0339(11) 0.0004(9) 0.0176(10) 0.0015(9) C7 0.0501(15) 0.0322(12) 0.0401(13) -0.0005(9) 0.0239(11) -0.0040(10) C4 0.0439(14) 0.0536(14) 0.0403(13) 0.0019(10) 0.0257(11) 0.0037(11) C2 0.0417(14) 0.0388(12) 0.0385(12) -0.0003(10) 0.0206(11) 0.0009(10) C20 0.0377(13) 0.0340(11) 0.0311(11) 0.0014(9) 0.0157(10) 0.0033(9) C17 0.0422(14) 0.0446(13) 0.0350(12) -0.0025(10) 0.0197(11) 0.0038(10) C3 0.0370(13) 0.0467(13) 0.0383(12) 0.0043(10) 0.0200(11) 0.0008(10) C14 0.0369(13) 0.0387(12) 0.0363(12) 0.0030(9) 0.0166(10) -0.0014(10) C1 0.0426(13) 0.0373(11) 0.0356(12) 0.0006(9) 0.0217(10) 0.0011(10) C19 0.0380(13) 0.0320(11) 0.0332(11) 0.0023(9) 0.0134(10) 0.0020(9) C16 0.0415(14) 0.0427(12) 0.0391(12) -0.0001(10) 0.0245(11) -0.0014(10) C13 0.0402(14) 0.0401(12) 0.0445(13) -0.0059(10) 0.0201(11) -0.0073(10) C12 0.0491(15) 0.0339(11) 0.0391(12) -0.0046(9) 0.0227(11) -0.0056(10) C5 0.0455(14) 0.0452(13) 0.0394(12) -0.0015(10) 0.0205(11) 0.0046(11) C11 0.0624(18) 0.0444(14) 0.0649(17) 0.0013(12) 0.0380(15) -0.0081(12) C6 0.0487(15) 0.0380(12) 0.0438(13) -0.0019(10) 0.0244(11) -0.0005(10) C10 0.095(2) 0.0416(15) 0.096(2) 0.0184(15) 0.058(2) 0.0023(15) C8 0.0572(17) 0.0466(14) 0.0629(17) 0.0100(12) 0.0345(14) 0.0107(12) C9 0.083(2) 0.0433(16) 0.090(2) 0.0236(15) 0.0477(18) 0.0162(14) C21 0.0516(16) 0.0597(16) 0.0491(14) -0.0137(12) 0.0301(13) -0.0015(12) C22 0.068(2) 0.082(2) 0.0686(19) -0.0174(16) 0.0481(16) -0.0059(16) C23 0.081(2) 0.0582(18) 0.102(3) -0.0173(16) 0.054(2) 0.0084(15) C24 0.073(2) 0.112(3) 0.0502(16) -0.0238(16) 0.0342(16) -0.0049(18) C25 0.0401(14) 0.0398(12) 0.0443(13) -0.0049(10) 0.0195(11) -0.0027(10) C26 0.0544(16) 0.0502(15) 0.0680(17) -0.0112(13) 0.0292(14) -0.0141(12) C27 0.0601(17) 0.0571(16) 0.0593(16) 0.0071(13) 0.0320(14) -0.0126(13) C28 0.0398(15) 0.0566(15) 0.0719(18) -0.0072(14) 0.0223(13) -0.0004(12) C29 0.0554(16) 0.0455(13) 0.0578(15) 0.0079(12) 0.0356(13) 0.0002(12) C30 0.082(2) 0.0613(17) 0.103(2) 0.0342(17) 0.061(2) 0.0193(16) C32 0.072(2) 0.0693(18) 0.0762(19) 0.0191(15) 0.0508(16) -0.0021(15) C31 0.084(2) 0.068(2) 0.082(2) -0.0132(16) 0.0444(18) -0.0306(16) C33 0.0628(18) 0.0527(15) 0.0500(15) -0.0091(12) 0.0330(13) 0.0051(13) C36 0.114(3) 0.0545(18) 0.087(2) -0.0243(16) 0.063(2) -0.0058(17) C34 0.073(2) 0.075(2) 0.079(2) -0.0016(17) 0.0407(18) 0.0220(16) C35 0.091(2) 0.083(2) 0.0501(16) -0.0140(15) 0.0335(16) 0.0041(17) O1 0.0576(10) 0.0344(8) 0.0531(9) -0.0045(7) 0.0375(8) -0.0036(7) O2 0.0533(10) 0.0353(8) 0.0466(9) -0.0070(7) 0.0330(8) -0.0060(7) N1 0.0439(11) 0.0334(9) 0.0395(10) 0.0017(8) 0.0242(9) 0.0004(8) N2 0.0393(11) 0.0320(9) 0.0337(10) -0.0013(7) 0.0181(8) -0.0006(8) _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 O2 1.8183(14) . ? Ni1 N2 1.8494(18) . ? Ni1 O1 1.8599(15) . ? Ni1 N1 1.8596(17) . ? C18 C19 1.386(3) . ? C18 C17 1.411(3) . ? C15 C20 1.408(3) . ? C15 C16 1.414(3) . ? C15 C14 1.437(3) . ? C7 N1 1.397(3) . ? C7 C12 1.403(3) . ? C7 C8 1.402(3) . ? C4 C3 1.369(3) . ? C4 C5 1.415(3) . ? C2 O1 1.310(3) . ? C2 C1 1.426(3) . ? C2 C3 1.430(3) . ? C20 O2 1.318(2) . ? C20 C19 1.425(3) . ? C17 C16 1.364(3) . ? C17 C21 1.539(3) . ? C3 C29 1.532(3) . ? C14 N2 1.302(3) . ? C1 N1 1.371(3) . ? C1 C6 1.415(3) . ? C19 C25 1.547(3) . ? C13 N2 1.485(3) . ? C13 C12 1.502(3) . ? C12 C11 1.381(3) . ? C5 C6 1.372(3) . ? C5 C33 1.538(3) . ? C11 C10 1.384(4) . ? C10 C9 1.379(4) . ? C8 C9 1.370(4) . ? C21 C24 1.526(4) . ? C21 C22 1.533(4) . ? C21 C23 1.542(4) . ? C25 C26 1.530(3) . ? C25 C27 1.537(3) . ? C25 C28 1.537(3) . ? C29 C32 1.533(3) . ? C29 C31 1.535(4) . ? C29 C30 1.537(4) . ? C33 C36 1.526(4) . ? C33 C34 1.536(4) . ? C33 C35 1.539(4) . ? 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 O2 Ni1 N2 94.74(7) . . ? O2 Ni1 O1 86.55(7) . . ? N2 Ni1 O1 169.34(7) . . ? O2 Ni1 N1 168.04(7) . . ? N2 Ni1 N1 94.97(8) . . ? O1 Ni1 N1 85.20(7) . . ? C19 C18 C17 124.4(2) . . ? C20 C15 C16 120.2(2) . . ? C20 C15 C14 121.26(19) . . ? C16 C15 C14 118.5(2) . . ? N1 C7 C12 117.94(19) . . ? N1 C7 C8 122.9(2) . . ? C12 C7 C8 119.1(2) . . ? C3 C4 C5 125.7(2) . . ? O1 C2 C1 116.2(2) . . ? O1 C2 C3 123.9(2) . . ? C1 C2 C3 119.9(2) . . ? O2 C20 C15 121.92(19) . . ? O2 C20 C19 118.97(19) . . ? C15 C20 C19 119.09(19) . . ? C16 C17 C18 116.93(19) . . ? C16 C17 C21 123.8(2) . . ? C18 C17 C21 119.3(2) . . ? C4 C3 C2 115.8(2) . . ? C4 C3 C29 123.7(2) . . ? C2 C3 C29 120.5(2) . . ? N2 C14 C15 125.2(2) . . ? N1 C1 C6 127.0(2) . . ? N1 C1 C2 111.93(18) . . ? C6 C1 C2 120.9(2) . . ? C18 C19 C20 117.4(2) . . ? C18 C19 C25 122.53(19) . . ? C20 C19 C25 120.11(18) . . ? C17 C16 C15 121.7(2) . . ? N2 C13 C12 111.15(17) . . ? C11 C12 C7 119.3(2) . . ? C11 C12 C13 121.4(2) . . ? C7 C12 C13 119.25(19) . . ? C6 C5 C4 118.4(2) . . ? C6 C5 C33 122.5(2) . . ? C4 C5 C33 119.2(2) . . ? C12 C11 C10 121.2(2) . . ? C5 C6 C1 119.3(2) . . ? C9 C10 C11 119.1(2) . . ? C9 C8 C7 120.0(2) . . ? C8 C9 C10 121.1(3) . . ? C24 C21 C22 108.7(2) . . ? C24 C21 C17 109.4(2) . . ? C22 C21 C17 111.7(2) . . ? C24 C21 C23 109.5(2) . . ? C22 C21 C23 108.0(2) . . ? C17 C21 C23 109.5(2) . . ? C26 C25 C27 108.3(2) . . ? C26 C25 C28 107.72(19) . . ? C27 C25 C28 109.7(2) . . ? C26 C25 C19 111.05(18) . . ? C27 C25 C19 110.00(18) . . ? C28 C25 C19 109.99(19) . . ? C3 C29 C32 111.7(2) . . ? C3 C29 C31 109.6(2) . . ? C32 C29 C31 108.2(2) . . ? C3 C29 C30 109.5(2) . . ? C32 C29 C30 107.7(2) . . ? C31 C29 C30 110.2(2) . . ? C36 C33 C34 109.2(2) . . ? C36 C33 C5 112.3(2) . . ? C34 C33 C5 108.6(2) . . ? C36 C33 C35 107.9(2) . . ? C34 C33 C35 109.6(2) . . ? C5 C33 C35 109.1(2) . . ? C2 O1 Ni1 112.87(14) . . ? C20 O2 Ni1 127.39(13) . . ? C1 N1 C7 122.91(18) . . ? C1 N1 Ni1 112.83(14) . . ? C7 N1 Ni1 123.44(14) . . ? C14 N2 C13 117.32(19) . . ? C14 N2 Ni1 125.31(16) . . ? C13 N2 Ni1 116.71(13) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.319 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 951780' ####################################################################### # # 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_cm_013c _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H45 N2 Ni O3' _chemical_formula_sum 'C36 H45 N2 Ni O3' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method 'dichloromethane, acetonitrile, ethanol' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour brown _diffrn_ambient_temperature 296(2) _chemical_formula_weight 612.45 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' 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _symmetry_space_group_name_Hall '-P 2ac 2ab' _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4633(3) _cell_length_b 18.9923(9) _cell_length_c 27.1870(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3337.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25383 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_unetI/netI 0.0951 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5666 _reflns_number_gt 3671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.1000P] 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 0.011(19) _refine_ls_number_reflns 5666 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.0913 _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 Ni1 Ni 0.14177(9) 0.42317(3) 0.582449(19) 0.04286(19) Uani 1 1 d . . . C2 C 0.1646(8) 0.3399(2) 0.66092(15) 0.0412(11) Uani 1 1 d . . . C7 C -0.2208(8) 0.3370(2) 0.56357(16) 0.0431(12) Uani 1 1 d . . . C18 C 0.6658(9) 0.6176(2) 0.52572(17) 0.0531(13) Uani 1 1 d . . . H18 H 0.7714 0.6491 0.5333 0.064 Uiso 1 1 calc R . . C29 C 0.3659(9) 0.3449(2) 0.74190(16) 0.0526(13) Uani 1 1 d . . . C19 C 0.5791(7) 0.5805(2) 0.56432(15) 0.0440(12) Uani 1 1 d . . . C15 C 0.3542(9) 0.5258(2) 0.50236(16) 0.0453(12) Uani 1 1 d . . . C8 C -0.3900(8) 0.3016(2) 0.58316(19) 0.0524(12) Uani 1 1 d . . . H8 H -0.3864 0.2879 0.6160 0.063 Uiso 1 1 calc R . . C13 C -0.0736(9) 0.4011(3) 0.48877(19) 0.0629(16) Uani 1 1 d . . . C12 C -0.2340(8) 0.3622(2) 0.51473(17) 0.0472(13) Uani 1 1 d . . . C5 C 0.0319(8) 0.2007(2) 0.67814(16) 0.0505(13) Uani 1 1 d . . . C31 C 0.5796(10) 0.3589(3) 0.7200(2) 0.081(2) Uani 1 1 d . . . H31A H 0.6426 0.3151 0.7108 0.122 Uiso 1 1 calc R . . H31B H 0.6646 0.3822 0.7439 0.122 Uiso 1 1 calc R . . H31C H 0.5658 0.3883 0.6914 0.122 Uiso 1 1 calc R . . C25 C 0.6508(8) 0.5888(2) 0.61765(15) 0.0474(12) Uani 1 1 d . . . C20 C 0.4161(8) 0.5312(2) 0.55243(16) 0.0425(13) Uani 1 1 d . . . C33 C -0.0221(10) 0.1239(3) 0.68975(18) 0.0641(16) Uani 1 1 d . . . C16 C 0.4529(8) 0.5664(3) 0.46521(16) 0.0546(14) Uani 1 1 d . . . H16 H 0.4095 0.5615 0.4328 0.065 Uiso 1 1 calc R . . C1 C 0.0187(8) 0.3060(2) 0.62935(15) 0.0410(12) Uani 1 1 d . . . C32 C 0.3962(11) 0.3024(3) 0.78968(17) 0.088(2) Uani 1 1 d . . . H32A H 0.2636 0.2902 0.8031 0.132 Uiso 1 1 calc R . . H32B H 0.4716 0.3303 0.8131 0.132 Uiso 1 1 calc R . . H32C H 0.4724 0.2602 0.7826 0.132 Uiso 1 1 calc R . . C4 C 0.1599(8) 0.2386(2) 0.71191(15) 0.0509(13) Uani 1 1 d . . . H4 H 0.1996 0.2156 0.7406 0.061 Uiso 1 1 calc R . . C17 C 0.6075(9) 0.6118(3) 0.47560(17) 0.0552(14) Uani 1 1 d . . . C6 C -0.0399(8) 0.2353(2) 0.63797(15) 0.0457(13) Uani 1 1 d . . . H6 H -0.1278 0.2126 0.6161 0.055 Uiso 1 1 calc R . . C14 C 0.1938(9) 0.4812(2) 0.48828(16) 0.0511(14) Uani 1 1 d . . . H14 H 0.1616 0.4812 0.4549 0.061 Uiso 1 1 calc R . . C3 C 0.2286(8) 0.3064(3) 0.70521(15) 0.0471(13) Uani 1 1 d . . . C26 C 0.8229(11) 0.6454(3) 0.62209(19) 0.083(2) Uani 1 1 d . . . H26A H 0.8633 0.6500 0.6559 0.125 Uiso 1 1 calc R . . H26B H 0.7716 0.6897 0.6103 0.125 Uiso 1 1 calc R . . H26C H 0.9404 0.6314 0.6028 0.125 Uiso 1 1 calc R . . C21 C 0.7154(10) 0.6575(3) 0.43645(19) 0.0719(18) Uani 1 1 d . . . C9 C -0.5613(9) 0.2862(3) 0.5558(2) 0.0600(15) Uani 1 1 d . . . H9 H -0.6699 0.2607 0.5695 0.072 Uiso 1 1 calc R . . C28 C 0.4677(9) 0.6130(3) 0.64966(17) 0.0691(16) Uani 1 1 d . . . H28A H 0.3589 0.5787 0.6480 0.104 Uiso 1 1 calc R . . H28B H 0.4175 0.6575 0.6378 0.104 Uiso 1 1 calc R . . H28C H 0.5126 0.6180 0.6831 0.104 Uiso 1 1 calc R . . C11 C -0.4125(9) 0.3469(3) 0.4880(2) 0.0614(16) Uani 1 1 d . . . H11 H -0.4232 0.3631 0.4559 0.074 Uiso 1 1 calc R . . C10 C -0.5714(9) 0.3092(3) 0.5073(2) 0.0619(16) Uani 1 1 d . . . H10 H -0.6866 0.2988 0.4881 0.074 Uiso 1 1 calc R . . C35 C -0.1512(14) 0.1214(3) 0.7372(2) 0.123(3) Uani 1 1 d . . . H35A H -0.0878 0.1506 0.7617 0.184 Uiso 1 1 calc R . . H35B H -0.1581 0.0738 0.7489 0.184 Uiso 1 1 calc R . . H35C H -0.2885 0.1382 0.7305 0.184 Uiso 1 1 calc R . . C24 C 0.9420(11) 0.6387(4) 0.4343(2) 0.109(3) Uani 1 1 d . . . H24A H 0.9582 0.5937 0.4186 0.163 Uiso 1 1 calc R . . H24B H 0.9969 0.6365 0.4671 0.163 Uiso 1 1 calc R . . H24C H 1.0151 0.6739 0.4158 0.163 Uiso 1 1 calc R . . C36 C 0.1750(12) 0.0809(3) 0.6971(3) 0.132(3) Uani 1 1 d . . . H36A H 0.2430 0.0747 0.6660 0.198 Uiso 1 1 calc R . . H36B H 0.1403 0.0357 0.7105 0.198 Uiso 1 1 calc R . . H36C H 0.2656 0.1053 0.7193 0.198 Uiso 1 1 calc R . . C27 C 0.7353(10) 0.5197(3) 0.63741(18) 0.0690(17) Uani 1 1 d . . . H27A H 0.6331 0.4835 0.6335 0.104 Uiso 1 1 calc R . . H27B H 0.7682 0.5250 0.6717 0.104 Uiso 1 1 calc R . . H27C H 0.8579 0.5071 0.6195 0.104 Uiso 1 1 calc R . . C34 C -0.1446(12) 0.0889(3) 0.6486(2) 0.107(3) Uani 1 1 d . . . H34A H -0.2701 0.1148 0.6430 0.160 Uiso 1 1 calc R . . H34B H -0.1777 0.0415 0.6578 0.160 Uiso 1 1 calc R . . H34C H -0.0632 0.0886 0.6190 0.160 Uiso 1 1 calc R . . C30 C 0.2667(10) 0.4160(3) 0.75659(18) 0.0862(19) Uani 1 1 d . . . H30A H 0.2659 0.4470 0.7287 0.129 Uiso 1 1 calc R . . H30B H 0.3453 0.4370 0.7827 0.129 Uiso 1 1 calc R . . H30C H 0.1272 0.4082 0.7675 0.129 Uiso 1 1 calc R . . C22 C 0.6098(13) 0.6523(4) 0.3870(2) 0.124(3) Uani 1 1 d . . . H22A H 0.6773 0.6831 0.3641 0.185 Uiso 1 1 calc R . . H22B H 0.4674 0.6658 0.3903 0.185 Uiso 1 1 calc R . . H22C H 0.6178 0.6047 0.3753 0.185 Uiso 1 1 calc R . . C23 C 0.7017(13) 0.7355(3) 0.4522(2) 0.116(3) Uani 1 1 d . . . H23A H 0.7631 0.7411 0.4841 0.175 Uiso 1 1 calc R . . H23B H 0.5592 0.7496 0.4535 0.175 Uiso 1 1 calc R . . H23C H 0.7743 0.7642 0.4288 0.175 Uiso 1 1 calc R . . N2 N 0.0801(6) 0.43828(18) 0.51631(13) 0.0450(10) Uani 1 1 d . . . N1 N -0.0416(6) 0.34847(17) 0.59072(13) 0.0421(9) Uani 1 1 d . . . O2 O 0.3339(5) 0.49396(13) 0.58667(10) 0.0483(8) Uani 1 1 d . . . O1 O 0.2290(5) 0.40155(14) 0.64623(10) 0.0473(8) Uani 1 1 d . . . O3 O -0.0716(8) 0.4019(2) 0.44370(12) 0.1066(17) 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 Ni1 0.0481(4) 0.0426(3) 0.0379(3) 0.0021(3) -0.0055(3) -0.0025(3) C2 0.041(3) 0.045(3) 0.038(2) -0.002(2) 0.004(2) 0.003(3) C7 0.034(3) 0.046(3) 0.049(3) -0.004(2) -0.003(3) 0.003(2) C18 0.048(4) 0.055(3) 0.057(3) 0.009(3) 0.006(3) -0.003(3) C29 0.068(4) 0.047(3) 0.043(3) 0.004(2) -0.008(3) -0.004(3) C19 0.044(3) 0.042(3) 0.046(3) 0.005(2) 0.000(2) 0.000(3) C15 0.050(3) 0.046(3) 0.040(3) 0.002(2) -0.005(3) 0.000(3) C8 0.041(4) 0.062(3) 0.055(3) -0.014(3) 0.010(3) 0.002(3) C13 0.080(5) 0.060(4) 0.049(3) 0.008(3) -0.016(3) -0.009(3) C12 0.053(4) 0.040(3) 0.048(3) 0.002(2) -0.013(3) 0.004(3) C5 0.056(4) 0.050(3) 0.045(3) 0.005(2) 0.004(3) -0.005(3) C31 0.079(6) 0.096(5) 0.068(4) 0.003(3) -0.023(4) -0.017(4) C25 0.051(3) 0.047(3) 0.044(3) 0.002(2) 0.000(3) -0.007(3) C20 0.044(4) 0.041(3) 0.042(3) 0.000(2) 0.001(2) 0.000(2) C33 0.098(5) 0.046(3) 0.049(3) 0.009(3) -0.004(3) -0.020(3) C16 0.061(4) 0.065(4) 0.038(3) 0.010(3) -0.003(3) 0.003(3) C1 0.041(3) 0.050(3) 0.033(2) 0.001(2) 0.007(2) 0.002(3) C32 0.133(7) 0.079(4) 0.052(3) 0.013(3) -0.026(4) -0.027(4) C4 0.065(4) 0.049(3) 0.039(2) 0.010(2) 0.000(3) -0.003(3) C17 0.050(4) 0.068(3) 0.048(3) 0.017(3) 0.007(3) -0.007(3) C6 0.051(4) 0.049(3) 0.037(3) -0.002(2) 0.001(2) -0.007(3) C14 0.067(4) 0.049(3) 0.037(3) 0.004(2) 0.000(3) 0.005(3) C3 0.050(3) 0.056(3) 0.035(3) 0.001(2) 0.002(2) 0.002(3) C26 0.095(6) 0.095(4) 0.060(3) 0.002(3) -0.011(4) -0.043(4) C21 0.070(5) 0.086(4) 0.060(4) 0.028(3) 0.004(3) -0.004(4) C9 0.038(4) 0.069(4) 0.073(4) -0.018(3) 0.001(3) 0.001(3) C28 0.085(5) 0.074(4) 0.049(3) -0.016(3) -0.002(3) 0.005(3) C11 0.064(5) 0.052(3) 0.069(4) -0.009(3) -0.024(3) 0.002(3) C10 0.046(4) 0.058(3) 0.082(4) -0.021(3) -0.017(3) 0.014(3) C35 0.199(9) 0.088(4) 0.081(4) 0.002(3) 0.058(5) -0.059(6) C24 0.071(5) 0.161(7) 0.094(5) 0.053(4) 0.030(4) 0.021(5) C36 0.132(7) 0.052(4) 0.211(8) 0.032(5) -0.030(7) -0.003(5) C27 0.074(5) 0.075(4) 0.058(3) 0.001(3) -0.016(3) 0.006(3) C34 0.182(7) 0.060(4) 0.077(4) 0.014(3) -0.022(5) -0.060(5) C30 0.121(6) 0.073(4) 0.064(3) -0.019(3) -0.016(3) 0.012(4) C22 0.113(7) 0.190(7) 0.068(4) 0.067(5) -0.002(4) -0.044(6) C23 0.137(8) 0.100(5) 0.112(5) 0.052(4) 0.018(5) -0.005(5) N2 0.052(3) 0.042(2) 0.041(2) 0.0026(18) -0.007(2) -0.003(2) N1 0.041(3) 0.043(2) 0.042(2) -0.0030(19) -0.004(2) -0.0019(19) O2 0.062(2) 0.0466(17) 0.0365(16) 0.0080(15) -0.003(2) -0.0150(17) O1 0.057(2) 0.0475(19) 0.0378(17) 0.0032(15) -0.0024(16) -0.0053(16) O3 0.146(5) 0.129(4) 0.045(2) 0.011(2) -0.026(2) -0.065(3) _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 O2 1.834(3) . ? Ni1 N1 1.862(4) . ? Ni1 N2 1.864(3) . ? Ni1 O1 1.869(3) . ? C2 O1 1.305(5) . ? C2 C3 1.423(6) . ? C2 C1 1.429(6) . ? C7 C8 1.390(6) . ? C7 N1 1.390(6) . ? C7 C12 1.414(6) . ? C18 C19 1.383(6) . ? C18 C17 1.418(6) . ? C29 C3 1.522(6) . ? C29 C31 1.528(8) . ? C29 C32 1.542(6) . ? C29 C30 1.548(7) . ? C19 C20 1.447(6) . ? C19 C25 1.530(6) . ? C15 C14 1.393(6) . ? C15 C16 1.422(6) . ? C15 C20 1.422(6) . ? C8 C9 1.365(7) . ? C13 O3 1.226(5) . ? C13 N2 1.431(6) . ? C13 C12 1.455(7) . ? C12 C11 1.394(7) . ? C5 C6 1.357(6) . ? C5 C4 1.430(6) . ? C5 C33 1.532(6) . ? C25 C27 1.519(6) . ? C25 C28 1.539(7) . ? C25 C26 1.551(7) . ? C20 O2 1.284(5) . ? C33 C34 1.524(7) . ? C33 C36 1.526(8) . ? C33 C35 1.536(8) . ? C16 C17 1.349(6) . ? C1 N1 1.380(5) . ? C1 C6 1.415(6) . ? C4 C3 1.375(6) . ? C17 C21 1.541(7) . ? C14 N2 1.336(5) . ? C21 C24 1.509(8) . ? C21 C22 1.510(8) . ? C21 C23 1.545(8) . ? C9 C10 1.391(7) . ? C11 C10 1.357(7) . ? 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 O2 Ni1 N1 169.10(14) . . ? O2 Ni1 N2 95.30(14) . . ? N1 Ni1 N2 95.60(16) . . ? O2 Ni1 O1 84.19(13) . . ? N1 Ni1 O1 84.98(15) . . ? N2 Ni1 O1 173.36(16) . . ? O1 C2 C3 124.6(4) . . ? O1 C2 C1 115.5(4) . . ? C3 C2 C1 119.9(4) . . ? C8 C7 N1 121.9(4) . . ? C8 C7 C12 118.4(5) . . ? N1 C7 C12 119.7(4) . . ? C19 C18 C17 125.5(5) . . ? C3 C29 C31 110.8(4) . . ? C3 C29 C32 112.0(4) . . ? C31 C29 C32 107.8(5) . . ? C3 C29 C30 110.2(5) . . ? C31 C29 C30 108.8(4) . . ? C32 C29 C30 107.0(4) . . ? C18 C19 C20 117.1(4) . . ? C18 C19 C25 123.0(4) . . ? C20 C19 C25 119.9(4) . . ? C14 C15 C16 117.9(4) . . ? C14 C15 C20 121.1(4) . . ? C16 C15 C20 121.0(5) . . ? C9 C8 C7 122.2(5) . . ? O3 C13 N2 120.6(5) . . ? O3 C13 C12 119.9(5) . . ? N2 C13 C12 119.4(4) . . ? C11 C12 C7 117.9(5) . . ? C11 C12 C13 116.3(5) . . ? C7 C12 C13 125.7(5) . . ? C6 C5 C4 118.0(4) . . ? C6 C5 C33 123.3(5) . . ? C4 C5 C33 118.6(4) . . ? C27 C25 C19 110.8(4) . . ? C27 C25 C28 109.5(4) . . ? C19 C25 C28 109.5(4) . . ? C27 C25 C26 108.2(4) . . ? C19 C25 C26 111.2(4) . . ? C28 C25 C26 107.5(4) . . ? O2 C20 C15 122.5(4) . . ? O2 C20 C19 119.7(4) . . ? C15 C20 C19 117.7(4) . . ? C34 C33 C36 107.2(5) . . ? C34 C33 C5 112.4(4) . . ? C36 C33 C5 110.2(5) . . ? C34 C33 C35 108.7(5) . . ? C36 C33 C35 109.1(5) . . ? C5 C33 C35 109.1(4) . . ? C17 C16 C15 122.0(4) . . ? N1 C1 C6 127.2(4) . . ? N1 C1 C2 112.4(4) . . ? C6 C1 C2 120.3(4) . . ? C3 C4 C5 125.0(4) . . ? C16 C17 C18 116.6(4) . . ? C16 C17 C21 123.4(5) . . ? C18 C17 C21 119.9(5) . . ? C5 C6 C1 120.2(5) . . ? N2 C14 C15 128.6(4) . . ? C4 C3 C2 115.9(4) . . ? C4 C3 C29 123.4(4) . . ? C2 C3 C29 120.6(4) . . ? C24 C21 C22 112.8(6) . . ? C24 C21 C17 109.5(5) . . ? C22 C21 C17 111.9(5) . . ? C24 C21 C23 107.1(6) . . ? C22 C21 C23 106.5(5) . . ? C17 C21 C23 108.8(5) . . ? C8 C9 C10 119.2(5) . . ? C10 C11 C12 122.4(5) . . ? C11 C10 C9 119.7(5) . . ? C14 N2 C13 112.6(4) . . ? C14 N2 Ni1 121.8(3) . . ? C13 N2 Ni1 125.3(3) . . ? C1 N1 C7 123.2(4) . . ? C1 N1 Ni1 110.9(3) . . ? C7 N1 Ni1 125.8(3) . . ? C20 O2 Ni1 129.7(3) . . ? C2 O1 Ni1 112.6(3) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.312 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 951781' ####################################################################### # # 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_cm010-01 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C28 H34 N2 O2' _chemical_formula_sum 'C28 H34 N2 O2' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method 'chloroform, ethanol' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour yellow _diffrn_ambient_temperature 296(2) _chemical_formula_weight 430.57 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' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5342(8) _cell_length_b 12.0945(10) _cell_length_c 12.3345(11) _cell_angle_alpha 62.280(4) _cell_angle_beta 83.074(5) _cell_angle_gamma 81.490(5) _cell_volume 1243.03(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13117 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_unetI/netI 0.0385 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3931 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1050P)^2^+0.0800P] 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 3931 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 C7 C 0.67577(16) 0.34153(14) 0.30363(14) 0.0349(4) Uani 1 1 d . . . C12 C 0.61339(16) 0.35434(14) 0.20038(15) 0.0382(4) Uani 1 1 d . . . C8 C 0.79404(17) 0.40439(16) 0.28610(16) 0.0440(4) Uani 1 1 d . . . H8 H 0.8364 0.3967 0.3537 0.053 Uiso 1 1 calc R . . C11 C 0.6718(2) 0.42767(16) 0.08488(16) 0.0497(5) Uani 1 1 d . . . H11 H 0.6312 0.4354 0.0165 0.060 Uiso 1 1 calc R . . C9 C 0.8490(2) 0.47789(18) 0.16945(19) 0.0551(5) Uani 1 1 d . . . H9 H 0.9277 0.5197 0.1593 0.066 Uiso 1 1 calc R . . C10 C 0.7895(2) 0.49018(18) 0.06829(19) 0.0588(5) Uani 1 1 d . . . H10 H 0.8273 0.5396 -0.0102 0.071 Uiso 1 1 calc R . . C14 C 0.55330(17) 0.10070(17) 0.19069(17) 0.0444(4) Uani 1 1 d . . . H14 H 0.5367 0.1514 0.1083 0.053 Uiso 1 1 calc R . . C15 C 0.60394(18) -0.03036(17) 0.23051(17) 0.0451(5) Uani 1 1 d . . . C13 C 0.48759(18) 0.28519(16) 0.21339(17) 0.0452(5) Uani 1 1 d . . . H13A H 0.4136 0.3011 0.2672 0.054 Uiso 1 1 calc R . . H13B H 0.4496 0.3158 0.1338 0.054 Uiso 1 1 calc R . . C20 C 0.62716(18) -0.11226(17) 0.35352(17) 0.0466(5) Uani 1 1 d . . . C19 C 0.6799(2) -0.23630(19) 0.3886(2) 0.0670(6) Uani 1 1 d . . . H19 H 0.6965 -0.2901 0.4704 0.080 Uiso 1 1 calc R . . C16 C 0.6342(2) -0.0778(2) 0.1450(2) 0.0650(6) Uani 1 1 d . . . H16 H 0.6196 -0.0248 0.0626 0.078 Uiso 1 1 calc R . . C17 C 0.6852(3) -0.2016(2) 0.1815(2) 0.0772(7) Uani 1 1 d . . . H17 H 0.7046 -0.2323 0.1241 0.093 Uiso 1 1 calc R . . C18 C 0.7074(2) -0.2799(2) 0.3032(2) 0.0762(7) Uani 1 1 d . . . H18 H 0.7416 -0.3636 0.3278 0.091 Uiso 1 1 calc R . . C2 C 0.69893(17) 0.29707(15) 0.58453(15) 0.0398(4) Uani 1 1 d . . . C6 C 0.76249(16) 0.09942(15) 0.57852(15) 0.0401(4) Uani 1 1 d . . . H6 H 0.7576 0.0489 0.5411 0.048 Uiso 1 1 calc R . . C3 C 0.77432(17) 0.25441(16) 0.68972(16) 0.0426(4) Uani 1 1 d . . . C1 C 0.69528(16) 0.22122(16) 0.52831(15) 0.0384(4) Uani 1 1 d . . . C5 C 0.83642(16) 0.05237(16) 0.68321(15) 0.0393(4) Uani 1 1 d . . . C4 C 0.84046(17) 0.13239(16) 0.73540(16) 0.0432(4) Uani 1 1 d . . . H4 H 0.8908 0.1020 0.8055 0.052 Uiso 1 1 calc R . . C25 C 0.91352(17) -0.08111(16) 0.74192(17) 0.0473(5) Uani 1 1 d . . . C28 C 0.8922(2) -0.1551(2) 0.6737(2) 0.0729(7) Uani 1 1 d . . . H22A H 0.7925 -0.1589 0.6729 0.109 Uiso 1 1 calc R . . H22B H 0.9390 -0.2386 0.7146 0.109 Uiso 1 1 calc R . . H22C H 0.9318 -0.1140 0.5910 0.109 Uiso 1 1 calc R . . C26 C 1.07270(19) -0.0746(2) 0.7410(2) 0.0717(7) Uani 1 1 d . . . H23A H 1.1211 -0.1580 0.7744 0.108 Uiso 1 1 calc R . . H23B H 1.0879 -0.0350 0.7898 0.108 Uiso 1 1 calc R . . H23C H 1.1090 -0.0266 0.6582 0.108 Uiso 1 1 calc R . . C27 C 0.8561(2) -0.1522(2) 0.8747(2) 0.0753(7) Uani 1 1 d . . . H24A H 0.7570 -0.1600 0.8762 0.113 Uiso 1 1 calc R . . H24B H 0.8679 -0.1069 0.9190 0.113 Uiso 1 1 calc R . . H24C H 0.9073 -0.2343 0.9124 0.113 Uiso 1 1 calc R . . C21 C 0.7824(2) 0.33861(19) 0.75115(18) 0.0565(5) Uani 1 1 d . . . C24 C 0.8654(3) 0.2699(2) 0.8674(2) 0.0705(6) Uani 1 1 d . . . H28A H 0.8213 0.1962 0.9243 0.106 Uiso 1 1 calc R . . H28B H 0.8656 0.3244 0.9043 0.106 Uiso 1 1 calc R . . H28C H 0.9614 0.2459 0.8466 0.106 Uiso 1 1 calc R . . C23 C 0.6323(3) 0.3811(3) 0.7874(2) 0.0911(9) Uani 1 1 d . . . H26A H 0.5796 0.4287 0.7153 0.137 Uiso 1 1 calc R . . H26B H 0.6384 0.4324 0.8268 0.137 Uiso 1 1 calc R . . H26C H 0.5851 0.3088 0.8429 0.137 Uiso 1 1 calc R . . C22 C 0.8609(3) 0.4526(2) 0.6610(2) 0.0861(8) Uani 1 1 d . . . H27A H 0.9569 0.4243 0.6448 0.129 Uiso 1 1 calc R . . H27B H 0.8612 0.5084 0.6963 0.129 Uiso 1 1 calc R . . H27C H 0.8133 0.4959 0.5856 0.129 Uiso 1 1 calc R . . N1 N 0.61554(14) 0.26919(13) 0.42129(12) 0.0415(4) Uani 1 1 d . . . H1N H 0.5288 0.2533 0.4294 0.050 Uiso 1 1 calc R . . N2 N 0.53050(14) 0.14943(13) 0.26411(13) 0.0430(4) Uani 1 1 d . . . O1 O 0.62874(14) 0.41612(11) 0.53374(12) 0.0549(4) Uani 1 1 d . . . H1O H 0.5789 0.4239 0.4804 0.082 Uiso 1 1 calc R . . O2 O 0.59932(15) -0.07315(12) 0.44130(11) 0.0576(4) Uani 1 1 d . . . H2O H 0.5709 0.0019 0.4095 0.086 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 C7 0.0403(8) 0.0296(9) 0.0350(10) -0.0161(7) -0.0040(7) 0.0017(7) C12 0.0461(9) 0.0291(9) 0.0379(10) -0.0150(8) -0.0057(7) 0.0022(7) C8 0.0486(9) 0.0419(10) 0.0460(11) -0.0232(9) -0.0044(8) -0.0057(8) C11 0.0656(11) 0.0425(11) 0.0377(11) -0.0163(9) -0.0079(9) 0.0004(9) C9 0.0580(11) 0.0483(12) 0.0597(13) -0.0236(10) 0.0046(10) -0.0182(9) C10 0.0728(13) 0.0492(12) 0.0454(12) -0.0144(9) 0.0106(10) -0.0166(10) C14 0.0490(9) 0.0445(11) 0.0383(10) -0.0160(9) -0.0037(8) -0.0100(8) C15 0.0464(9) 0.0453(11) 0.0482(12) -0.0244(9) 0.0050(8) -0.0138(8) C13 0.0501(9) 0.0390(10) 0.0468(11) -0.0188(9) -0.0129(8) 0.0000(8) C20 0.0483(9) 0.0430(11) 0.0481(12) -0.0216(9) 0.0093(8) -0.0105(8) C19 0.0731(13) 0.0442(12) 0.0663(14) -0.0159(11) 0.0148(11) -0.0028(10) C16 0.0796(14) 0.0637(14) 0.0602(14) -0.0360(12) 0.0079(11) -0.0146(11) C17 0.0950(16) 0.0652(16) 0.0873(19) -0.0526(15) 0.0252(13) -0.0170(13) C18 0.0866(15) 0.0477(13) 0.0896(19) -0.0347(14) 0.0299(13) -0.0095(11) C2 0.0461(9) 0.0351(9) 0.0374(10) -0.0169(8) -0.0060(7) 0.0022(7) C6 0.0428(9) 0.0374(10) 0.0418(11) -0.0204(8) 0.0026(7) -0.0053(7) C3 0.0475(9) 0.0430(10) 0.0384(10) -0.0205(8) -0.0045(8) 0.0002(8) C1 0.0395(8) 0.0416(10) 0.0311(9) -0.0141(8) -0.0027(7) -0.0038(7) C5 0.0381(8) 0.0381(10) 0.0376(10) -0.0145(8) -0.0011(7) -0.0023(7) C4 0.0455(9) 0.0449(11) 0.0369(10) -0.0165(8) -0.0094(7) 0.0007(8) C25 0.0437(9) 0.0356(10) 0.0546(12) -0.0150(9) -0.0048(8) 0.0017(7) C28 0.0754(14) 0.0466(12) 0.0994(18) -0.0367(12) -0.0207(12) 0.0104(10) C26 0.0468(11) 0.0592(13) 0.1012(18) -0.0320(13) -0.0084(11) 0.0048(9) C27 0.0774(14) 0.0521(13) 0.0677(15) -0.0040(11) -0.0031(11) -0.0052(11) C21 0.0692(12) 0.0567(13) 0.0546(13) -0.0344(11) -0.0199(10) 0.0059(10) C24 0.0958(16) 0.0677(14) 0.0616(14) -0.0383(12) -0.0283(12) 0.0016(12) C23 0.0950(17) 0.121(2) 0.0892(19) -0.0819(18) -0.0232(14) 0.0309(16) C22 0.124(2) 0.0541(14) 0.0858(18) -0.0274(13) -0.0351(15) -0.0169(14) N1 0.0405(7) 0.0464(9) 0.0344(8) -0.0145(7) -0.0041(6) -0.0074(6) N2 0.0480(8) 0.0411(9) 0.0417(9) -0.0185(7) -0.0056(6) -0.0087(6) O1 0.0699(8) 0.0421(7) 0.0553(9) -0.0252(7) -0.0237(6) 0.0139(6) O2 0.0769(9) 0.0444(8) 0.0453(8) -0.0162(6) 0.0021(7) -0.0073(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 C7 C8 1.392(2) . ? C7 N1 1.403(2) . ? C7 C12 1.404(2) . ? C12 C11 1.380(2) . ? C12 C13 1.513(2) . ? C8 C9 1.379(3) . ? C11 C10 1.387(3) . ? C9 C10 1.369(3) . ? C14 N2 1.275(2) . ? C14 C15 1.447(2) . ? C15 C20 1.396(3) . ? C15 C16 1.402(3) . ? C13 N2 1.470(2) . ? C20 O2 1.355(2) . ? C20 C19 1.384(3) . ? C19 C18 1.365(3) . ? C16 C17 1.376(3) . ? C17 C18 1.375(3) . ? C2 O1 1.3749(19) . ? C2 C1 1.389(2) . ? C2 C3 1.400(2) . ? C6 C5 1.380(2) . ? C6 C1 1.390(2) . ? C3 C4 1.389(2) . ? C3 C21 1.540(2) . ? C1 N1 1.434(2) . ? C5 C4 1.396(2) . ? C5 C25 1.536(2) . ? C25 C27 1.528(3) . ? C25 C26 1.530(2) . ? C25 C28 1.531(3) . ? C21 C24 1.531(3) . ? C21 C23 1.534(3) . ? C21 C22 1.541(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 C8 C7 N1 121.61(15) . . ? C8 C7 C12 118.81(15) . . ? N1 C7 C12 119.55(14) . . ? C11 C12 C7 119.16(15) . . ? C11 C12 C13 119.45(15) . . ? C7 C12 C13 121.34(15) . . ? C9 C8 C7 120.62(17) . . ? C12 C11 C10 121.63(17) . . ? C10 C9 C8 120.96(17) . . ? C9 C10 C11 118.83(17) . . ? N2 C14 C15 122.62(16) . . ? C20 C15 C16 118.15(17) . . ? C20 C15 C14 121.51(16) . . ? C16 C15 C14 120.32(17) . . ? N2 C13 C12 110.39(12) . . ? O2 C20 C19 118.30(17) . . ? O2 C20 C15 121.37(16) . . ? C19 C20 C15 120.33(18) . . ? C18 C19 C20 120.1(2) . . ? C17 C16 C15 120.8(2) . . ? C18 C17 C16 119.7(2) . . ? C19 C18 C17 120.9(2) . . ? O1 C2 C1 118.73(14) . . ? O1 C2 C3 120.35(15) . . ? C1 C2 C3 120.91(15) . . ? C5 C6 C1 120.92(16) . . ? C4 C3 C2 116.33(16) . . ? C4 C3 C21 122.18(15) . . ? C2 C3 C21 121.49(15) . . ? C2 C1 C6 120.32(15) . . ? C2 C1 N1 118.65(14) . . ? C6 C1 N1 120.97(15) . . ? C6 C5 C4 117.07(15) . . ? C6 C5 C25 123.04(15) . . ? C4 C5 C25 119.89(15) . . ? C3 C4 C5 124.41(16) . . ? C27 C25 C26 108.76(17) . . ? C27 C25 C28 108.17(17) . . ? C26 C25 C28 108.74(17) . . ? C27 C25 C5 109.57(14) . . ? C26 C25 C5 109.70(15) . . ? C28 C25 C5 111.84(15) . . ? C24 C21 C23 107.79(18) . . ? C24 C21 C3 111.97(16) . . ? C23 C21 C3 110.02(17) . . ? C24 C21 C22 107.43(18) . . ? C23 C21 C22 110.8(2) . . ? C3 C21 C22 108.76(17) . . ? C7 N1 C1 121.48(13) . . ? C14 N2 C13 118.46(15) . . ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 0.325 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 951782'