# 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_mo26_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N2 O' _chemical_formula_sum 'C22 H30 N2 O' _chemical_formula_weight 338.48 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.4201(10) _cell_length_b 8.0500(3) _cell_length_c 16.4354(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.222(2) _cell_angle_gamma 90.00 _cell_volume 4157.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5419 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.39 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5459 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14550 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_unetI/netI 0.0793 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4091 _reflns_number_gt 1689 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 SHELXL _refine_ls_extinction_coef 0.0085(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4091 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1552 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.2064 _refine_ls_wR_factor_gt 0.1831 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 O O 0.28141(7) 0.1732(3) -0.24104(13) 0.1002(7) Uani 1 1 d . . . N1 N 0.37310(6) 0.1119(3) 0.01350(11) 0.0637(6) Uani 1 1 d . . . H1A H 0.3544 0.1791 -0.0062 0.076 Uiso 1 1 calc R . . N2 N 0.29902(7) 0.1608(3) -0.06721(12) 0.0741(7) Uani 1 1 d . . . C1 C 0.36494(7) -0.0533(3) 0.00791(13) 0.0590(6) Uani 1 1 d . . . C2 C 0.32675(8) -0.1086(3) -0.02941(13) 0.0647(7) Uani 1 1 d . . . C3 C 0.31925(11) -0.2791(4) -0.03314(19) 0.0867(9) Uani 1 1 d . . . H3A H 0.2941 -0.3157 -0.0572 0.104 Uiso 1 1 calc R . . C4 C 0.34648(13) -0.3933(4) -0.0037(2) 0.1038(11) Uani 1 1 d . . . H4A H 0.3404 -0.5061 -0.0076 0.125 Uiso 1 1 calc R . . C5 C 0.38405(11) -0.3387(4) 0.0328(2) 0.0968(10) Uani 1 1 d . . . H5A H 0.4033 -0.4156 0.0537 0.116 Uiso 1 1 calc R . . C6 C 0.39267(9) -0.1730(4) 0.03822(17) 0.0787(8) Uani 1 1 d . . . H6A H 0.4179 -0.1391 0.0629 0.094 Uiso 1 1 calc R . . C7 C 0.41016(8) 0.1822(3) 0.04952(16) 0.0664(7) Uani 1 1 d . . . C8 C 0.41036(10) 0.2172(4) 0.13307(17) 0.0793(8) Uani 1 1 d . . . C9 C 0.44594(13) 0.2888(5) 0.1665(2) 0.1115(12) Uani 1 1 d . . . H9A H 0.4469 0.3100 0.2221 0.134 Uiso 1 1 calc R . . C10 C 0.47968(14) 0.3290(5) 0.1195(3) 0.1228(14) Uani 1 1 d . . . H10A H 0.5032 0.3803 0.1432 0.147 Uiso 1 1 calc R . . C11 C 0.47990(11) 0.2954(5) 0.0377(3) 0.1086(12) Uani 1 1 d . . . H11A H 0.5037 0.3221 0.0070 0.130 Uiso 1 1 calc R . . C12 C 0.44461(9) 0.2214(4) -0.00019(19) 0.0792(8) Uani 1 1 d . . . C13 C 0.37327(12) 0.1768(5) 0.18696(18) 0.0981(11) Uani 1 1 d . . . H13A H 0.3531 0.1131 0.1536 0.118 Uiso 1 1 calc R . . C14 C 0.38488(17) 0.0672(7) 0.2587(3) 0.164(2) Uani 1 1 d . . . H14A H 0.3988 -0.0314 0.2394 0.246 Uiso 1 1 calc R . . H14B H 0.3595 0.0370 0.2875 0.246 Uiso 1 1 calc R . . H14C H 0.4037 0.1265 0.2945 0.246 Uiso 1 1 calc R . . C15 C 0.34976(16) 0.3307(7) 0.2151(3) 0.1468(16) Uani 1 1 d . . . H15A H 0.3422 0.3972 0.1687 0.220 Uiso 1 1 calc R . . H15B H 0.3678 0.3940 0.2508 0.220 Uiso 1 1 calc R . . H15C H 0.3244 0.2985 0.2435 0.220 Uiso 1 1 calc R . . C16 C 0.44300(10) 0.1857(4) -0.0908(2) 0.0917(10) Uani 1 1 d . . . H16A H 0.4252 0.0871 -0.0991 0.110 Uiso 1 1 calc R . . C17 C 0.48664(15) 0.1496(7) -0.1263(3) 0.1511(18) Uani 1 1 d . . . H17A H 0.4993 0.0575 -0.0980 0.227 Uiso 1 1 calc R . . H17B H 0.5045 0.2457 -0.1202 0.227 Uiso 1 1 calc R . . H17C H 0.4838 0.1229 -0.1829 0.227 Uiso 1 1 calc R . . C18 C 0.42199(14) 0.3308(5) -0.1352(2) 0.1197(12) Uani 1 1 d . . . H18A H 0.3942 0.3498 -0.1130 0.180 Uiso 1 1 calc R . . H18B H 0.4195 0.3052 -0.1920 0.180 Uiso 1 1 calc R . . H18C H 0.4390 0.4288 -0.1283 0.180 Uiso 1 1 calc R . . C19 C 0.29555(8) 0.0043(4) -0.06390(15) 0.0723(7) Uani 1 1 d . . . H19A H 0.2709 -0.0423 -0.0854 0.087 Uiso 1 1 calc R . . C20 C 0.26524(9) 0.2556(5) -0.1078(2) 0.0965(10) Uani 1 1 d . . . H20A H 0.2579 0.3514 -0.0748 0.116 Uiso 1 1 calc R . . H20B H 0.2400 0.1867 -0.1130 0.116 Uiso 1 1 calc R . . C21 C 0.27878(11) 0.3116(4) -0.1890(2) 0.0928(9) Uani 1 1 d . . . H21A H 0.2584 0.3910 -0.2106 0.111 Uiso 1 1 calc R . . H21B H 0.3063 0.3658 -0.1853 0.111 Uiso 1 1 calc R . . C22 C 0.29837(14) 0.2109(6) -0.3169(2) 0.1343(16) Uani 1 1 d . . . H22A H 0.2994 0.1120 -0.3495 0.201 Uiso 1 1 calc R . . H22B H 0.3266 0.2545 -0.3102 0.201 Uiso 1 1 calc R . . H22C H 0.2808 0.2921 -0.3435 0.201 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 O 0.1130(16) 0.1049(19) 0.0829(13) -0.0021(13) 0.0050(12) -0.0004(12) N1 0.0647(12) 0.0499(13) 0.0763(12) 0.0022(11) -0.0128(9) -0.0037(10) N2 0.0689(13) 0.0808(18) 0.0725(12) 0.0002(13) -0.0049(10) 0.0038(13) C1 0.0670(14) 0.0530(17) 0.0569(12) 0.0003(12) 0.0030(10) -0.0039(13) C2 0.0677(14) 0.0667(18) 0.0596(12) -0.0097(13) 0.0048(11) -0.0110(14) C3 0.093(2) 0.068(2) 0.0996(19) -0.0104(18) -0.0044(16) -0.0237(18) C4 0.129(3) 0.054(2) 0.129(3) -0.007(2) -0.006(2) -0.016(2) C5 0.111(2) 0.061(2) 0.118(2) 0.0043(19) -0.007(2) 0.0077(19) C6 0.0834(18) 0.0607(19) 0.0920(18) 0.0081(16) -0.0064(15) -0.0052(15) C7 0.0698(15) 0.0508(16) 0.0785(15) 0.0093(13) -0.0171(12) -0.0088(12) C8 0.100(2) 0.0620(18) 0.0762(16) 0.0019(14) -0.0248(15) -0.0141(15) C9 0.122(3) 0.112(3) 0.099(2) 0.006(2) -0.044(2) -0.036(2) C10 0.118(3) 0.112(3) 0.138(3) 0.010(3) -0.060(3) -0.036(2) C11 0.079(2) 0.101(3) 0.146(3) 0.024(2) -0.014(2) -0.0218(17) C12 0.0730(17) 0.068(2) 0.0964(19) 0.0125(16) -0.0054(15) -0.0112(14) C13 0.126(3) 0.102(3) 0.0663(16) -0.0009(18) -0.0034(17) -0.018(2) C14 0.202(5) 0.177(5) 0.112(3) 0.053(3) 0.018(3) 0.012(4) C15 0.136(3) 0.151(4) 0.153(4) -0.013(3) 0.004(3) 0.007(3) C16 0.089(2) 0.090(2) 0.096(2) 0.0113(18) 0.0121(17) -0.0056(17) C17 0.129(3) 0.181(5) 0.144(3) 0.018(3) 0.039(3) 0.024(3) C18 0.133(3) 0.121(3) 0.106(2) 0.015(2) -0.009(2) 0.003(2) C19 0.0670(15) 0.085(2) 0.0646(14) -0.0051(15) -0.0003(11) -0.0175(16) C20 0.083(2) 0.108(3) 0.099(2) 0.0039(19) -0.0053(16) 0.0219(18) C21 0.095(2) 0.087(2) 0.096(2) 0.007(2) -0.0126(17) 0.0147(17) C22 0.143(3) 0.169(4) 0.090(2) 0.029(3) 0.010(2) 0.034(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 O C22 1.392(4) . ? O C21 1.407(4) . ? N1 C1 1.357(3) . ? N1 C7 1.422(3) . ? N1 H1A 0.8600 . ? N2 C19 1.266(3) . ? N2 C20 1.465(4) . ? C1 C6 1.390(4) . ? C1 C2 1.417(3) . ? C2 C3 1.394(4) . ? C2 C19 1.451(4) . ? C3 C4 1.345(5) . ? C3 H3A 0.9300 . ? C4 C5 1.393(5) . ? C4 H4A 0.9300 . ? C5 C6 1.364(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C12 1.395(4) . ? C7 C8 1.402(4) . ? C8 C9 1.371(5) . ? C8 C13 1.502(4) . ? C9 C10 1.353(5) . ? C9 H9A 0.9300 . ? C10 C11 1.371(6) . ? C10 H10A 0.9300 . ? C11 C12 1.403(5) . ? C11 H11A 0.9300 . ? C12 C16 1.517(5) . ? C13 C15 1.516(6) . ? C13 C14 1.516(5) . ? C13 H13A 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.520(5) . ? C16 C18 1.526(5) . ? C16 H16A 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9300 . ? C20 C21 1.474(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 O C21 113.3(3) . . ? C1 N1 C7 124.9(2) . . ? C1 N1 H1A 117.5 . . ? C7 N1 H1A 117.5 . . ? C19 N2 C20 118.4(3) . . ? N1 C1 C6 122.5(2) . . ? N1 C1 C2 119.8(2) . . ? C6 C1 C2 117.8(2) . . ? C3 C2 C1 118.1(3) . . ? C3 C2 C19 119.1(2) . . ? C1 C2 C19 122.8(2) . . ? C4 C3 C2 123.4(3) . . ? C4 C3 H3A 118.3 . . ? C2 C3 H3A 118.3 . . ? C3 C4 C5 118.4(3) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C1 122.0(3) . . ? C5 C6 H6A 119.0 . . ? C1 C6 H6A 119.0 . . ? C12 C7 C8 121.9(2) . . ? C12 C7 N1 118.8(2) . . ? C8 C7 N1 119.2(2) . . ? C9 C8 C7 118.5(3) . . ? C9 C8 C13 119.2(3) . . ? C7 C8 C13 122.2(2) . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C7 C12 C11 116.7(3) . . ? C7 C12 C16 120.6(3) . . ? C11 C12 C16 122.7(3) . . ? C8 C13 C15 112.5(3) . . ? C8 C13 C14 113.5(3) . . ? C15 C13 C14 110.8(3) . . ? C8 C13 H13A 106.5 . . ? C15 C13 H13A 106.5 . . ? C14 C13 H13A 106.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 112.7(3) . . ? C12 C16 C18 109.7(3) . . ? C17 C16 C18 110.6(3) . . ? C12 C16 H16A 107.9 . . ? C17 C16 H16A 107.9 . . ? C18 C16 H16A 107.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C2 125.6(2) . . ? N2 C19 H19A 117.2 . . ? C2 C19 H19A 117.2 . . ? N2 C20 C21 111.1(2) . . ? N2 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? N2 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? O C21 C20 109.0(3) . . ? O C21 H21A 109.9 . . ? C20 C21 H21A 109.9 . . ? O C21 H21B 109.9 . . ? C20 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? O C22 H22A 109.5 . . ? O C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C7 N1 C1 C6 0.5(3) . . . . ? C7 N1 C1 C2 180.0(2) . . . . ? N1 C1 C2 C3 -179.2(2) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? N1 C1 C2 C19 1.1(3) . . . . ? C6 C1 C2 C19 -179.4(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C19 C2 C3 C4 179.2(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C4 C5 C6 C1 -0.1(5) . . . . ? N1 C1 C6 C5 179.5(2) . . . . ? C2 C1 C6 C5 0.0(4) . . . . ? C1 N1 C7 C12 94.2(3) . . . . ? C1 N1 C7 C8 -88.7(3) . . . . ? C12 C7 C8 C9 -1.4(4) . . . . ? N1 C7 C8 C9 -178.4(3) . . . . ? C12 C7 C8 C13 179.5(3) . . . . ? N1 C7 C8 C13 2.5(4) . . . . ? C7 C8 C9 C10 1.8(6) . . . . ? C13 C8 C9 C10 -179.0(4) . . . . ? C8 C9 C10 C11 -1.8(7) . . . . ? C9 C10 C11 C12 1.4(7) . . . . ? C8 C7 C12 C11 1.0(4) . . . . ? N1 C7 C12 C11 178.0(3) . . . . ? C8 C7 C12 C16 -178.5(3) . . . . ? N1 C7 C12 C16 -1.5(4) . . . . ? C10 C11 C12 C7 -1.0(5) . . . . ? C10 C11 C12 C16 178.5(4) . . . . ? C9 C8 C13 C15 71.5(5) . . . . ? C7 C8 C13 C15 -109.3(4) . . . . ? C9 C8 C13 C14 -55.3(5) . . . . ? C7 C8 C13 C14 123.8(4) . . . . ? C7 C12 C16 C17 -150.1(3) . . . . ? C11 C12 C16 C17 30.4(5) . . . . ? C7 C12 C16 C18 86.2(3) . . . . ? C11 C12 C16 C18 -93.3(4) . . . . ? C20 N2 C19 C2 177.1(2) . . . . ? C3 C2 C19 N2 -177.4(3) . . . . ? C1 C2 C19 N2 2.3(4) . . . . ? C19 N2 C20 C21 -103.9(3) . . . . ? C22 O C21 C20 -173.5(3) . . . . ? N2 C20 C21 O 70.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N2 0.86 2.01 2.704(3) 136.8 . _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.140 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 928698' ####################################################################### # # 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_mo8_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H34 N2 O Zn' _chemical_formula_sum 'C24 H34 N2 O Zn' _chemical_formula_weight 431.90 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0897(3) _cell_length_b 21.5824(7) _cell_length_c 10.7341(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.916(2) _cell_angle_gamma 90.00 _cell_volume 2278.32(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9932 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 28.28 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5999 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20551 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0493 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5609 _reflns_number_gt 4280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0290P)^2^+2.4500P] 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 5609 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Zn Zn 0.00171(2) 0.364036(11) 0.37332(3) 0.01707(8) Uani 1 1 d . . . O O -0.16603(18) 0.45736(8) 0.03216(16) 0.0288(4) Uani 1 1 d . . . N1 N 0.17064(17) 0.40996(8) 0.41963(17) 0.0133(4) Uani 1 1 d . . . N2 N -0.10876(17) 0.43695(8) 0.29681(18) 0.0156(4) Uani 1 1 d . . . C1 C 0.1833(2) 0.47278(9) 0.4249(2) 0.0126(4) Uani 1 1 d . . . C2 C 0.0706(2) 0.51289(9) 0.3780(2) 0.0135(4) Uani 1 1 d . . . C3 C 0.0897(2) 0.57774(9) 0.3862(2) 0.0159(4) Uani 1 1 d . . . H3A H 0.0156 0.6034 0.3553 0.019 Uiso 1 1 calc R . . C4 C 0.2135(2) 0.60432(9) 0.4379(2) 0.0179(5) Uani 1 1 d . . . H4A H 0.2231 0.6472 0.4433 0.021 Uiso 1 1 calc R . . C5 C 0.3247(2) 0.56526(9) 0.4821(2) 0.0172(5) Uani 1 1 d . . . H5A H 0.4094 0.5825 0.5167 0.021 Uiso 1 1 calc R . . C6 C 0.3108(2) 0.50191(9) 0.4753(2) 0.0164(4) Uani 1 1 d . . . H6A H 0.3871 0.4773 0.5045 0.020 Uiso 1 1 calc R . . C7 C 0.2921(2) 0.37337(9) 0.4335(2) 0.0155(4) Uani 1 1 d . . . C8 C 0.3556(2) 0.34844(9) 0.5523(2) 0.0161(4) Uani 1 1 d . . . C9 C 0.4627(2) 0.30656(9) 0.5579(2) 0.0194(5) Uani 1 1 d . . . H9A H 0.5046 0.2890 0.6359 0.023 Uiso 1 1 calc R . . C10 C 0.5069(2) 0.29091(9) 0.4493(2) 0.0210(5) Uani 1 1 d . . . H10A H 0.5760 0.2619 0.4538 0.025 Uiso 1 1 calc R . . C11 C 0.4485(2) 0.31845(10) 0.3335(2) 0.0196(5) Uani 1 1 d . . . H11A H 0.4819 0.3090 0.2616 0.024 Uiso 1 1 calc R . . C12 C 0.3404(2) 0.36015(9) 0.3225(2) 0.0157(4) Uani 1 1 d . . . C13 C 0.3124(2) 0.36840(10) 0.6733(2) 0.0211(5) Uani 1 1 d . . . H13A H 0.2553 0.4053 0.6519 0.025 Uiso 1 1 calc R . . C14 C 0.4336(3) 0.38666(13) 0.7797(3) 0.0341(6) Uani 1 1 d . . . H14A H 0.4859 0.4180 0.7489 0.051 Uiso 1 1 calc R . . H14B H 0.4897 0.3510 0.8060 0.051 Uiso 1 1 calc R . . H14C H 0.4016 0.4025 0.8512 0.051 Uiso 1 1 calc R . . C15 C 0.2256(3) 0.31876(11) 0.7186(3) 0.0293(6) Uani 1 1 d . . . H15A H 0.1498 0.3085 0.6502 0.044 Uiso 1 1 calc R . . H15B H 0.1929 0.3342 0.7900 0.044 Uiso 1 1 calc R . . H15C H 0.2796 0.2824 0.7439 0.044 Uiso 1 1 calc R . . C16 C 0.2784(2) 0.39072(11) 0.1957(2) 0.0208(5) Uani 1 1 d . . . H16A H 0.2139 0.4220 0.2119 0.025 Uiso 1 1 calc R . . C17 C 0.3855(3) 0.42429(14) 0.1402(3) 0.0370(7) Uani 1 1 d . . . H17A H 0.4338 0.4532 0.2019 0.055 Uiso 1 1 calc R . . H17B H 0.3417 0.4461 0.0642 0.055 Uiso 1 1 calc R . . H17C H 0.4482 0.3946 0.1196 0.055 Uiso 1 1 calc R . . C18 C 0.1986(3) 0.34467(13) 0.0995(3) 0.0375(7) Uani 1 1 d . . . H18A H 0.1318 0.3243 0.1362 0.056 Uiso 1 1 calc R . . H18B H 0.2597 0.3144 0.0783 0.056 Uiso 1 1 calc R . . H18C H 0.1541 0.3663 0.0235 0.056 Uiso 1 1 calc R . . C19 C -0.0629(2) 0.49286(10) 0.3129(2) 0.0156(4) Uani 1 1 d . . . H19A H -0.1236 0.5240 0.2782 0.019 Uiso 1 1 calc R . . C20 C -0.2448(2) 0.42884(11) 0.2150(2) 0.0199(5) Uani 1 1 d . . . H20A H -0.2950 0.4674 0.2101 0.024 Uiso 1 1 calc R . . H20B H -0.2940 0.3975 0.2512 0.024 Uiso 1 1 calc R . . C21 C -0.2329(2) 0.40933(11) 0.0825(2) 0.0241(5) Uani 1 1 d . . . H21A H -0.1813 0.3712 0.0869 0.029 Uiso 1 1 calc R . . H21B H -0.3224 0.4024 0.0284 0.029 Uiso 1 1 calc R . . C22 C -0.1416(3) 0.44289(14) -0.0892(3) 0.0380(7) Uani 1 1 d . . . H22A H -0.0963 0.4771 -0.1192 0.057 Uiso 1 1 calc R . . H22B H -0.2266 0.4352 -0.1483 0.057 Uiso 1 1 calc R . . H22C H -0.0854 0.4066 -0.0826 0.057 Uiso 1 1 calc R . . C23 C -0.0480(2) 0.27619(10) 0.3785(3) 0.0280(6) Uani 1 1 d . . . H23A H 0.0296 0.2515 0.3692 0.034 Uiso 1 1 calc R . . H23B H -0.0642 0.2675 0.4624 0.034 Uiso 1 1 calc R . . C24 C -0.1717(3) 0.25428(12) 0.2787(3) 0.0461(8) Uani 1 1 d . . . H24A H -0.1861 0.2109 0.2905 0.069 Uiso 1 1 calc R . . H24B H -0.1564 0.2611 0.1946 0.069 Uiso 1 1 calc R . . H24C H -0.2505 0.2771 0.2882 0.069 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 Zn 0.01315(12) 0.01422(12) 0.02362(15) -0.00094(11) 0.00365(9) -0.00222(10) O 0.0351(10) 0.0360(10) 0.0163(9) 0.0021(8) 0.0077(7) -0.0030(8) N1 0.0107(8) 0.0132(8) 0.0157(10) -0.0001(7) 0.0027(7) 0.0012(7) N2 0.0112(8) 0.0201(9) 0.0163(10) -0.0005(7) 0.0049(7) -0.0002(7) C1 0.0146(10) 0.0140(9) 0.0105(11) -0.0011(8) 0.0054(8) -0.0005(8) C2 0.0136(10) 0.0139(9) 0.0142(11) 0.0008(8) 0.0058(8) 0.0017(8) C3 0.0179(10) 0.0153(10) 0.0159(12) 0.0009(8) 0.0069(8) 0.0046(8) C4 0.0230(11) 0.0116(10) 0.0214(13) 0.0007(9) 0.0096(9) 0.0005(8) C5 0.0155(10) 0.0153(10) 0.0216(12) -0.0008(9) 0.0062(9) -0.0026(8) C6 0.0113(10) 0.0149(10) 0.0235(12) 0.0005(9) 0.0053(9) 0.0024(8) C7 0.0109(9) 0.0085(9) 0.0277(13) -0.0020(8) 0.0057(8) -0.0019(7) C8 0.0162(10) 0.0113(9) 0.0212(12) 0.0004(8) 0.0049(9) -0.0017(8) C9 0.0170(11) 0.0125(10) 0.0272(14) 0.0028(9) 0.0016(9) 0.0010(8) C10 0.0144(10) 0.0101(10) 0.0371(15) -0.0047(9) 0.0030(10) 0.0023(8) C11 0.0163(11) 0.0163(10) 0.0269(13) -0.0080(9) 0.0059(9) -0.0010(9) C12 0.0129(10) 0.0143(9) 0.0196(12) -0.0026(9) 0.0027(8) -0.0015(8) C13 0.0252(12) 0.0182(10) 0.0200(12) 0.0030(9) 0.0053(9) 0.0062(9) C14 0.0384(15) 0.0357(14) 0.0265(15) -0.0045(12) 0.0034(12) 0.0007(12) C15 0.0302(13) 0.0288(13) 0.0321(15) 0.0086(11) 0.0140(11) 0.0080(11) C16 0.0172(11) 0.0245(11) 0.0215(13) -0.0025(10) 0.0058(9) 0.0028(9) C17 0.0272(14) 0.0505(17) 0.0346(17) 0.0135(14) 0.0100(12) 0.0032(12) C18 0.0399(16) 0.0374(15) 0.0278(16) -0.0050(12) -0.0084(12) 0.0014(12) C19 0.0140(10) 0.0194(10) 0.0148(11) 0.0008(9) 0.0058(8) 0.0038(8) C20 0.0126(10) 0.0253(11) 0.0211(13) -0.0005(10) 0.0020(9) -0.0015(9) C21 0.0200(11) 0.0286(12) 0.0224(13) -0.0029(10) 0.0018(9) -0.0031(10) C22 0.0366(15) 0.0588(19) 0.0204(14) 0.0039(13) 0.0103(12) 0.0069(14) C23 0.0238(12) 0.0169(11) 0.0434(17) 0.0004(11) 0.0076(11) -0.0016(10) C24 0.0512(19) 0.0238(14) 0.057(2) -0.0038(13) -0.0018(16) -0.0169(13) _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 Zn N1 1.9380(17) . ? Zn C23 1.965(2) . ? Zn N2 1.9961(18) . ? O C21 1.409(3) . ? O C22 1.414(3) . ? N1 C1 1.362(3) . ? N1 C7 1.437(3) . ? N2 C19 1.290(3) . ? N2 C20 1.465(3) . ? C1 C6 1.426(3) . ? C1 C2 1.428(3) . ? C2 C3 1.413(3) . ? C2 C19 1.438(3) . ? C3 C4 1.374(3) . ? C3 H3A 0.9300 . ? C4 C5 1.399(3) . ? C4 H4A 0.9300 . ? C5 C6 1.375(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.400(3) . ? C7 C12 1.414(3) . ? C8 C9 1.400(3) . ? C8 C13 1.522(3) . ? C9 C10 1.380(3) . ? C9 H9A 0.9300 . ? C10 C11 1.385(3) . ? C10 H10A 0.9300 . ? C11 C12 1.399(3) . ? C11 H11A 0.9300 . ? C12 C16 1.516(3) . ? C13 C14 1.527(3) . ? C13 C15 1.530(3) . ? C13 H13A 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C18 1.527(3) . ? C16 C17 1.528(3) . ? C16 H16A 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9300 . ? C20 C21 1.514(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.527(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn C23 134.55(9) . . ? N1 Zn N2 94.62(7) . . ? C23 Zn N2 130.52(9) . . ? C21 O C22 112.8(2) . . ? C1 N1 C7 118.21(16) . . ? C1 N1 Zn 126.08(14) . . ? C7 N1 Zn 115.22(12) . . ? C19 N2 C20 116.87(18) . . ? C19 N2 Zn 122.12(15) . . ? C20 N2 Zn 120.97(14) . . ? N1 C1 C6 121.55(18) . . ? N1 C1 C2 121.92(18) . . ? C6 C1 C2 116.51(18) . . ? C3 C2 C1 119.47(19) . . ? C3 C2 C19 115.31(18) . . ? C1 C2 C19 125.06(18) . . ? C4 C3 C2 122.5(2) . . ? C4 C3 H3A 118.7 . . ? C2 C3 H3A 118.7 . . ? C3 C4 C5 118.25(19) . . ? C3 C4 H4A 120.9 . . ? C5 C4 H4A 120.9 . . ? C6 C5 C4 121.2(2) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C1 122.1(2) . . ? C5 C6 H6A 119.0 . . ? C1 C6 H6A 119.0 . . ? C8 C7 C12 121.04(19) . . ? C8 C7 N1 120.79(19) . . ? C12 C7 N1 118.06(19) . . ? C9 C8 C7 118.6(2) . . ? C9 C8 C13 120.8(2) . . ? C7 C8 C13 120.53(19) . . ? C10 C9 C8 120.9(2) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C11 120.0(2) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C10 C11 C12 121.3(2) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C11 C12 C7 117.9(2) . . ? C11 C12 C16 120.9(2) . . ? C7 C12 C16 121.18(18) . . ? C8 C13 C14 112.1(2) . . ? C8 C13 C15 111.51(19) . . ? C14 C13 C15 111.3(2) . . ? C8 C13 H13A 107.2 . . ? C14 C13 H13A 107.2 . . ? C15 C13 H13A 107.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C18 111.9(2) . . ? C12 C16 C17 111.73(19) . . ? C18 C16 C17 110.9(2) . . ? C12 C16 H16A 107.3 . . ? C18 C16 H16A 107.3 . . ? C17 C16 H16A 107.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C2 128.0(2) . . ? N2 C19 H19A 116.0 . . ? C2 C19 H19A 116.0 . . ? N2 C20 C21 109.60(18) . . ? N2 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? N2 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? H20A C20 H20B 108.2 . . ? O C21 C20 107.54(19) . . ? O C21 H21A 110.2 . . ? C20 C21 H21A 110.2 . . ? O C21 H21B 110.2 . . ? C20 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? O C22 H22A 109.5 . . ? O C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 Zn 116.93(18) . . ? C24 C23 H23A 108.1 . . ? Zn C23 H23A 108.1 . . ? C24 C23 H23B 108.1 . . ? Zn C23 H23B 108.1 . . ? H23A C23 H23B 107.3 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 C23 Zn N1 C1 -170.76(18) . . . . ? N2 Zn N1 C1 15.40(18) . . . . ? C23 Zn N1 C7 17.4(2) . . . . ? N2 Zn N1 C7 -156.40(15) . . . . ? N1 Zn N2 C19 -12.53(18) . . . . ? C23 Zn N2 C19 173.24(18) . . . . ? N1 Zn N2 C20 165.06(16) . . . . ? C23 Zn N2 C20 -9.2(2) . . . . ? C7 N1 C1 C6 -16.3(3) . . . . ? Zn N1 C1 C6 172.08(16) . . . . ? C7 N1 C1 C2 162.4(2) . . . . ? Zn N1 C1 C2 -9.2(3) . . . . ? N1 C1 C2 C3 179.90(19) . . . . ? C6 C1 C2 C3 -1.3(3) . . . . ? N1 C1 C2 C19 -4.9(3) . . . . ? C6 C1 C2 C19 173.9(2) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C19 C2 C3 C4 -175.7(2) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? N1 C1 C6 C5 -179.4(2) . . . . ? C2 C1 C6 C5 1.8(3) . . . . ? C1 N1 C7 C8 96.3(2) . . . . ? Zn N1 C7 C8 -91.2(2) . . . . ? C1 N1 C7 C12 -87.5(2) . . . . ? Zn N1 C7 C12 84.94(19) . . . . ? C12 C7 C8 C9 -4.4(3) . . . . ? N1 C7 C8 C9 171.67(18) . . . . ? C12 C7 C8 C13 173.41(19) . . . . ? N1 C7 C8 C13 -10.6(3) . . . . ? C7 C8 C9 C10 1.3(3) . . . . ? C13 C8 C9 C10 -176.5(2) . . . . ? C8 C9 C10 C11 2.3(3) . . . . ? C9 C10 C11 C12 -2.9(3) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C10 C11 C12 C16 179.2(2) . . . . ? C8 C7 C12 C11 3.8(3) . . . . ? N1 C7 C12 C11 -172.35(18) . . . . ? C8 C7 C12 C16 -175.50(19) . . . . ? N1 C7 C12 C16 8.4(3) . . . . ? C9 C8 C13 C14 47.3(3) . . . . ? C7 C8 C13 C14 -130.5(2) . . . . ? C9 C8 C13 C15 -78.3(3) . . . . ? C7 C8 C13 C15 104.0(2) . . . . ? C11 C12 C16 C18 70.2(3) . . . . ? C7 C12 C16 C18 -110.6(2) . . . . ? C11 C12 C16 C17 -54.9(3) . . . . ? C7 C12 C16 C17 124.4(2) . . . . ? C20 N2 C19 C2 -173.8(2) . . . . ? Zn N2 C19 C2 3.9(3) . . . . ? C3 C2 C19 N2 -176.9(2) . . . . ? C1 C2 C19 N2 7.7(4) . . . . ? C19 N2 C20 C21 99.1(2) . . . . ? Zn N2 C20 C21 -78.6(2) . . . . ? C22 O C21 C20 176.5(2) . . . . ? N2 C20 C21 O -61.8(2) . . . . ? N1 Zn C23 C24 -150.86(19) . . . . ? N2 Zn C23 C24 21.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.645 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 928699' ####################################################################### # # 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_mo17_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C58 H72 N4 O4 Zn2' _chemical_formula_sum 'C58 H72 N4 O4 Zn2' _chemical_formula_weight 1019.94 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4830(3) _cell_length_b 12.5950(4) _cell_length_c 12.6403(4) _cell_angle_alpha 104.2100(10) _cell_angle_beta 108.1830(10) _cell_angle_gamma 103.9290(10) _cell_volume 1305.32(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9536 _cell_measurement_theta_min 2.373 _cell_measurement_theta_max 28.320 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7599 _exptl_absorpt_correction_T_max 0.8684 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 23060 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.0173 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.35 _reflns_number_total 6458 _reflns_number_gt 6056 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0503P)^2^+1.4069P] 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 6458 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Zn1 Zn 0.58910(2) 0.629759(16) 0.553220(16) 0.01368(7) Uani 1 1 d . . . O1 O 0.45512(16) 0.86968(12) 0.35852(12) 0.0228(3) Uani 1 1 d . . . O2 O 0.62631(14) 0.47978(11) 0.50799(12) 0.0172(2) Uani 1 1 d . . . N1 N 0.62382(17) 0.73045(12) 0.45656(12) 0.0140(3) Uani 1 1 d . . . N2 N 0.71261(17) 0.75415(13) 0.70808(12) 0.0149(3) Uani 1 1 d . . . C1 C 0.5237(2) 0.69912(15) 0.33068(15) 0.0177(3) Uani 1 1 d . . . H1A H 0.4803 0.6132 0.2921 0.021 Uiso 1 1 calc R . . H1B H 0.5880 0.7316 0.2901 0.021 Uiso 1 1 calc R . . C2 C 0.3891(2) 0.74676(16) 0.31893(16) 0.0204(3) Uani 1 1 d . . . H2A H 0.3130 0.7161 0.2351 0.024 Uiso 1 1 calc R . . H2B H 0.3324 0.7229 0.3677 0.024 Uiso 1 1 calc R . . C3 C 0.3406(2) 0.92290(19) 0.36589(19) 0.0271(4) Uani 1 1 d . . . H3A H 0.2518 0.8924 0.2884 0.041 Uiso 1 1 calc R . . H3B H 0.3887 1.0076 0.3889 0.041 Uiso 1 1 calc R . . H3C H 0.3023 0.9054 0.4254 0.041 Uiso 1 1 calc R . . C4 C 0.7423(2) 0.82680(14) 0.50388(14) 0.0144(3) Uani 1 1 d . . . H4 H 0.7607 0.8661 0.4516 0.017 Uiso 1 1 calc R . . C5 C 0.85021(19) 0.88205(14) 0.62668(14) 0.0143(3) Uani 1 1 d . . . C6 C 0.9785(2) 0.98104(15) 0.64970(15) 0.0184(3) Uani 1 1 d . . . H6 H 0.9880 1.0024 0.5845 0.022 Uiso 1 1 calc R . . C7 C 1.0903(2) 1.04806(16) 0.76167(16) 0.0210(3) Uani 1 1 d . . . H7 H 1.1771 1.1129 0.7740 0.025 Uiso 1 1 calc R . . C8 C 1.0718(2) 1.01754(16) 0.85699(16) 0.0199(3) Uani 1 1 d . . . H8 H 1.1470 1.0628 0.9354 0.024 Uiso 1 1 calc R . . C9 C 0.9473(2) 0.92349(16) 0.83933(15) 0.0182(3) Uani 1 1 d . . . H9 H 0.9373 0.9070 0.9066 0.022 Uiso 1 1 calc R . . C10 C 0.83203(19) 0.84936(14) 0.72398(14) 0.0142(3) Uani 1 1 d . . . C11 C 0.6887(2) 0.73814(15) 0.81053(15) 0.0167(3) Uani 1 1 d . . . C12 C 0.7749(3) 0.6825(2) 0.87648(19) 0.0302(4) Uani 1 1 d . . . C13 C 0.9177(3) 0.6568(2) 0.8565(2) 0.0328(5) Uani 1 1 d . . . H13 H 0.9352 0.6877 0.7942 0.039 Uiso 1 1 calc R . . C14 C 0.8803(3) 0.5256(2) 0.8118(2) 0.0392(5) Uani 1 1 d . . . H14A H 0.8650 0.4942 0.8726 0.059 Uiso 1 1 calc R . . H14B H 0.9682 0.5088 0.7948 0.059 Uiso 1 1 calc R . . H14C H 0.7835 0.4893 0.7391 0.059 Uiso 1 1 calc R . . C15 C 1.0735(3) 0.7134(2) 0.9709(2) 0.0367(5) Uani 1 1 d . . . H15A H 1.0613 0.6788 1.0304 0.055 Uiso 1 1 calc R . . H15B H 1.0960 0.7976 1.0027 0.055 Uiso 1 1 calc R . . H15C H 1.1611 0.6992 0.9514 0.055 Uiso 1 1 calc R . . C16 C 0.7355(3) 0.6562(2) 0.9670(2) 0.0349(5) Uani 1 1 d . . . H16 H 0.7902 0.6161 1.0099 0.042 Uiso 1 1 calc R . . C17 C 0.6176(3) 0.68779(18) 0.99535(17) 0.0261(4) Uani 1 1 d . . . H17 H 0.5883 0.6660 1.0544 0.031 Uiso 1 1 calc R . . C18 C 0.5434(2) 0.75107(17) 0.93721(16) 0.0219(4) Uani 1 1 d . . . H18 H 0.4682 0.7773 0.9607 0.026 Uiso 1 1 calc R . . C19 C 0.5765(2) 0.77742(15) 0.84438(15) 0.0171(3) Uani 1 1 d . . . C20 C 0.4965(2) 0.85075(18) 0.78550(16) 0.0237(4) Uani 1 1 d . . . H20 H 0.4968 0.8332 0.7040 0.028 Uiso 1 1 calc R . . C21 C 0.5906(3) 0.98057(19) 0.8552(2) 0.0306(4) Uani 1 1 d . . . H21A H 0.5924 0.9998 0.9357 0.046 Uiso 1 1 calc R . . H21B H 0.5405 1.0273 0.8151 0.046 Uiso 1 1 calc R . . H21C H 0.6990 0.9977 0.8595 0.046 Uiso 1 1 calc R . . C22 C 0.3244(3) 0.8255(2) 0.7732(2) 0.0332(5) Uani 1 1 d . . . H22A H 0.2668 0.7413 0.7364 0.050 Uiso 1 1 calc R . . H22B H 0.2742 0.8655 0.7234 0.050 Uiso 1 1 calc R . . H22C H 0.3222 0.8537 0.8520 0.050 Uiso 1 1 calc R . . C23 C 0.7618(2) 0.46322(15) 0.49187(16) 0.0176(3) Uani 1 1 d . . . H23A H 0.7347 0.3808 0.4433 0.021 Uiso 1 1 calc R . . H23B H 0.8456 0.4799 0.5701 0.021 Uiso 1 1 calc R . . C24 C 0.8232(2) 0.54155(15) 0.43139(16) 0.0167(3) Uani 1 1 d . . . C25 C 0.9500(2) 0.64532(16) 0.49700(18) 0.0216(4) Uani 1 1 d . . . H25 H 1.0004 0.6661 0.5806 0.026 Uiso 1 1 calc R . . C26 C 1.0036(2) 0.71904(18) 0.4412(2) 0.0296(4) Uani 1 1 d . . . H26 H 1.0904 0.7898 0.4868 0.036 Uiso 1 1 calc R . . C27 C 0.9309(3) 0.6895(2) 0.3196(2) 0.0341(5) Uani 1 1 d . . . H27 H 0.9682 0.7394 0.2814 0.041 Uiso 1 1 calc R . . C28 C 0.8034(3) 0.5867(2) 0.2538(2) 0.0319(5) Uani 1 1 d . . . H28 H 0.7527 0.5665 0.1703 0.038 Uiso 1 1 calc R . . C29 C 0.7493(2) 0.51313(17) 0.30908(17) 0.0234(4) Uani 1 1 d . . . H29 H 0.6615 0.4430 0.2634 0.028 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 Zn1 0.01301(10) 0.01383(10) 0.01699(11) 0.00675(7) 0.00754(8) 0.00576(7) O1 0.0207(6) 0.0213(6) 0.0284(7) 0.0099(5) 0.0083(5) 0.0114(5) O2 0.0128(5) 0.0160(5) 0.0270(6) 0.0080(5) 0.0110(5) 0.0074(4) N1 0.0147(6) 0.0156(6) 0.0135(6) 0.0053(5) 0.0058(5) 0.0075(5) N2 0.0152(6) 0.0182(7) 0.0138(6) 0.0071(5) 0.0074(5) 0.0061(5) C1 0.0186(8) 0.0188(8) 0.0139(7) 0.0041(6) 0.0048(6) 0.0076(6) C2 0.0173(8) 0.0197(8) 0.0204(8) 0.0057(7) 0.0033(7) 0.0067(7) C3 0.0278(10) 0.0303(10) 0.0314(10) 0.0132(8) 0.0134(8) 0.0187(8) C4 0.0164(7) 0.0169(7) 0.0148(7) 0.0077(6) 0.0086(6) 0.0084(6) C5 0.0142(7) 0.0158(7) 0.0149(7) 0.0058(6) 0.0067(6) 0.0065(6) C6 0.0198(8) 0.0197(8) 0.0172(8) 0.0077(6) 0.0093(7) 0.0056(7) C7 0.0187(8) 0.0198(8) 0.0207(8) 0.0055(7) 0.0075(7) 0.0023(7) C8 0.0184(8) 0.0217(8) 0.0156(8) 0.0035(6) 0.0048(6) 0.0055(7) C9 0.0196(8) 0.0226(8) 0.0137(7) 0.0070(6) 0.0074(6) 0.0077(7) C10 0.0147(7) 0.0168(7) 0.0149(7) 0.0064(6) 0.0076(6) 0.0084(6) C11 0.0178(8) 0.0195(8) 0.0163(7) 0.0083(6) 0.0094(6) 0.0070(6) C12 0.0426(12) 0.0396(11) 0.0310(10) 0.0241(9) 0.0245(9) 0.0269(10) C13 0.0358(11) 0.0334(11) 0.0318(11) 0.0163(9) 0.0121(9) 0.0127(9) C14 0.0418(13) 0.0366(12) 0.0433(13) 0.0151(10) 0.0168(11) 0.0192(10) C15 0.0225(10) 0.0397(12) 0.0356(12) 0.0067(10) 0.0053(9) 0.0047(9) C16 0.0535(14) 0.0423(12) 0.0337(11) 0.0277(10) 0.0278(11) 0.0296(11) C17 0.0325(10) 0.0280(10) 0.0204(9) 0.0110(7) 0.0158(8) 0.0051(8) C18 0.0178(8) 0.0293(9) 0.0163(8) 0.0041(7) 0.0093(7) 0.0046(7) C19 0.0146(7) 0.0203(8) 0.0133(7) 0.0032(6) 0.0048(6) 0.0045(6) C20 0.0265(9) 0.0341(10) 0.0170(8) 0.0088(7) 0.0102(7) 0.0193(8) C21 0.0352(11) 0.0301(10) 0.0398(12) 0.0185(9) 0.0218(10) 0.0179(9) C22 0.0249(10) 0.0387(12) 0.0292(10) 0.0008(9) 0.0047(8) 0.0185(9) C23 0.0143(7) 0.0199(8) 0.0245(8) 0.0097(7) 0.0107(7) 0.0099(6) C24 0.0140(7) 0.0187(8) 0.0229(8) 0.0080(6) 0.0104(6) 0.0100(6) C25 0.0162(8) 0.0219(8) 0.0289(9) 0.0073(7) 0.0106(7) 0.0094(7) C26 0.0221(9) 0.0214(9) 0.0540(13) 0.0153(9) 0.0224(9) 0.0099(7) C27 0.0392(12) 0.0373(11) 0.0571(14) 0.0331(11) 0.0366(11) 0.0255(10) C28 0.0405(12) 0.0442(12) 0.0304(10) 0.0223(9) 0.0226(9) 0.0261(10) C29 0.0239(9) 0.0262(9) 0.0226(9) 0.0079(7) 0.0107(7) 0.0117(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 Zn1 O2 1.9512(12) 2_666 ? Zn1 N2 1.9591(15) . ? Zn1 O2 1.9841(12) . ? Zn1 N1 2.0051(14) . ? Zn1 Zn1 3.0187(4) 2_666 ? O1 C2 1.413(2) . ? O1 C3 1.421(2) . ? O2 C23 1.4172(19) . ? O2 Zn1 1.9513(12) 2_666 ? N1 C4 1.289(2) . ? N1 C1 1.469(2) . ? N2 C10 1.359(2) . ? N2 C11 1.435(2) . ? C1 C2 1.519(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.441(2) . ? C4 H4 0.9500 . ? C5 C6 1.411(2) . ? C5 C10 1.435(2) . ? C6 C7 1.373(3) . ? C6 H6 0.9500 . ? C7 C8 1.399(3) . ? C7 H7 0.9500 . ? C8 C9 1.371(3) . ? C8 H8 0.9500 . ? C9 C10 1.428(2) . ? C9 H9 0.9500 . ? C11 C12 1.411(3) . ? C11 C19 1.412(2) . ? C12 C16 1.397(3) . ? C12 C13 1.545(3) . ? C13 C14 1.519(3) . ? C13 C15 1.561(3) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.389(3) . ? C16 H16 0.9500 . ? C17 C18 1.381(3) . ? C17 H17 0.9500 . ? C18 C19 1.399(2) . ? C18 H18 0.9500 . ? C19 C20 1.518(2) . ? C20 C21 1.532(3) . ? C20 C22 1.535(3) . ? C20 H20 1.0000 . ? 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 1.506(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.389(3) . ? C24 C29 1.393(3) . ? C25 C26 1.391(3) . ? C25 H25 0.9500 . ? C26 C27 1.382(4) . ? C26 H26 0.9500 . ? C27 C28 1.385(4) . ? C27 H27 0.9500 . ? C28 C29 1.387(3) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? 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 Zn1 N2 129.24(6) 2_666 . ? O2 Zn1 O2 79.82(5) 2_666 . ? N2 Zn1 O2 123.49(6) . . ? O2 Zn1 N1 114.40(6) 2_666 . ? N2 Zn1 N1 95.77(6) . . ? O2 Zn1 N1 115.84(5) . . ? O2 Zn1 Zn1 40.31(3) 2_666 2_666 ? N2 Zn1 Zn1 140.50(4) . 2_666 ? O2 Zn1 Zn1 39.51(4) . 2_666 ? N1 Zn1 Zn1 123.61(4) . 2_666 ? C2 O1 C3 111.66(15) . . ? C23 O2 Zn1 130.17(11) . 2_666 ? C23 O2 Zn1 127.05(11) . . ? Zn1 O2 Zn1 100.18(5) 2_666 . ? C4 N1 C1 116.55(14) . . ? C4 N1 Zn1 119.79(11) . . ? C1 N1 Zn1 123.63(11) . . ? C10 N2 C11 118.58(14) . . ? C10 N2 Zn1 122.10(11) . . ? C11 N2 Zn1 118.93(11) . . ? N1 C1 C2 110.17(14) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? O1 C2 C1 107.66(14) . . ? O1 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O1 C3 H3A 109.5 . . ? O1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C5 127.71(15) . . ? N1 C4 H4 116.1 . . ? C5 C4 H4 116.1 . . ? C6 C5 C10 119.33(15) . . ? C6 C5 C4 114.60(15) . . ? C10 C5 C4 125.96(15) . . ? C7 C6 C5 123.23(16) . . ? C7 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? C6 C7 C8 117.65(17) . . ? C6 C7 H7 121.2 . . ? C8 C7 H7 121.2 . . ? C9 C8 C7 121.25(16) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 122.67(16) . . ? C8 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? N2 C10 C9 121.77(15) . . ? N2 C10 C5 122.42(15) . . ? C9 C10 C5 115.81(15) . . ? C12 C11 C19 120.02(16) . . ? C12 C11 N2 120.55(15) . . ? C19 C11 N2 119.43(15) . . ? C16 C12 C11 118.89(19) . . ? C16 C12 C13 119.15(19) . . ? C11 C12 C13 121.85(17) . . ? C14 C13 C12 109.2(2) . . ? C14 C13 C15 108.80(19) . . ? C12 C13 C15 113.24(19) . . ? C14 C13 H13 108.5 . . ? C12 C13 H13 108.5 . . ? C15 C13 H13 108.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C12 121.03(19) . . ? C17 C16 H16 119.5 . . ? C12 C16 H16 119.5 . . ? C18 C17 C16 119.59(18) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 121.36(17) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C11 118.70(16) . . ? C18 C19 C20 119.75(16) . . ? C11 C19 C20 121.51(16) . . ? C19 C20 C21 109.92(16) . . ? C19 C20 C22 113.43(18) . . ? C21 C20 C22 109.35(16) . . ? C19 C20 H20 108.0 . . ? C21 C20 H20 108.0 . . ? C22 C20 H20 108.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O2 C23 C24 111.33(13) . . ? O2 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 . . ? O2 C23 H23B 109.4 . . ? C24 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C25 C24 C29 119.00(17) . . ? C25 C24 C23 120.67(16) . . ? C29 C24 C23 120.28(16) . . ? C24 C25 C26 120.53(19) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C27 C26 C25 120.1(2) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 119.68(19) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C29 120.4(2) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C28 C29 C24 120.30(19) . . ? C28 C29 H29 119.9 . . ? C24 C29 H29 119.9 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.306 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 928700' ####################################################################### # # 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_mo20_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H58 N4 O2 Zn' _chemical_formula_sum 'C44 H58 N4 O2 Zn' _chemical_formula_weight 740.31 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6979(2) _cell_length_b 13.3403(2) _cell_length_c 14.2243(2) _cell_angle_alpha 92.6920(10) _cell_angle_beta 96.9920(10) _cell_angle_gamma 104.5650(10) _cell_volume 1943.78(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9617 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 28.29 _exptl_crystal_description cube _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9357 _exptl_absorpt_correction_T_max 0.9357 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32685 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.29 _reflns_number_total 9617 _reflns_number_gt 8339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0316P)^2^+1.0923P] 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 9617 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Zn Zn 0.215958(15) 0.232395(12) 0.288224(11) 0.01176(5) Uani 1 1 d . . . O1 O 0.37196(12) 0.08258(9) 0.48764(8) 0.0274(3) Uani 1 1 d . . . O2 O 0.46072(12) -0.03627(9) 0.20869(9) 0.0307(3) Uani 1 1 d . . . N1 N 0.31305(11) 0.36388(9) 0.24525(8) 0.0129(2) Uani 1 1 d . . . N2 N 0.29806(12) 0.26949(9) 0.42883(8) 0.0149(2) Uani 1 1 d . . . N3 N 0.29487(11) 0.11163(9) 0.26321(8) 0.0142(2) Uani 1 1 d . . . N4 N 0.03336(11) 0.15127(9) 0.25791(8) 0.0135(2) Uani 1 1 d . . . C1 C 0.22600(14) 0.01743(11) 0.26348(10) 0.0164(3) Uani 1 1 d . . . H1A H 0.2718 -0.0350 0.2627 0.020 Uiso 1 1 calc R . . C2 C 0.08691(14) -0.01763(10) 0.26484(10) 0.0140(3) Uani 1 1 d . . . C3 C 0.04139(15) -0.12597(11) 0.26981(11) 0.0183(3) Uani 1 1 d . . . H3A H 0.1030 -0.1664 0.2738 0.022 Uiso 1 1 calc R . . C4 C -0.08774(15) -0.17544(11) 0.26913(11) 0.0205(3) Uani 1 1 d . . . H4A H -0.1154 -0.2484 0.2733 0.025 Uiso 1 1 calc R . . C5 C -0.17711(15) -0.11482(11) 0.26214(11) 0.0189(3) Uani 1 1 d . . . H5A H -0.2673 -0.1475 0.2602 0.023 Uiso 1 1 calc R . . C6 C -0.13750(14) -0.00908(11) 0.25802(10) 0.0162(3) Uani 1 1 d . . . H6A H -0.2015 0.0292 0.2536 0.019 Uiso 1 1 calc R . . C7 C -0.00385(13) 0.04565(10) 0.26013(9) 0.0130(3) Uani 1 1 d . . . C8 C -0.06996(13) 0.20178(10) 0.23614(10) 0.0140(3) Uani 1 1 d . . . C9 C -0.12769(14) 0.24018(11) 0.30927(11) 0.0165(3) Uani 1 1 d . . . C10 C -0.08982(15) 0.22640(12) 0.41317(11) 0.0195(3) Uani 1 1 d . . . H10A H -0.0299 0.1796 0.4168 0.023 Uiso 1 1 calc R . . C11 C -0.01654(16) 0.33081(13) 0.46708(12) 0.0264(3) Uani 1 1 d . . . H11A H 0.0593 0.3625 0.4363 0.040 Uiso 1 1 calc R . . H11B H 0.0126 0.3196 0.5329 0.040 Uiso 1 1 calc R . . H11C H -0.0747 0.3771 0.4666 0.040 Uiso 1 1 calc R . . C12 C -0.20873(17) 0.17616(13) 0.46089(12) 0.0279(4) Uani 1 1 d . . . H12A H -0.2551 0.1094 0.4261 0.042 Uiso 1 1 calc R . . H12B H -0.2672 0.2222 0.4604 0.042 Uiso 1 1 calc R . . H12C H -0.1799 0.1647 0.5267 0.042 Uiso 1 1 calc R . . C13 C -0.22372(14) 0.29220(11) 0.28520(11) 0.0200(3) Uani 1 1 d . . . H13A H -0.2619 0.3192 0.3342 0.024 Uiso 1 1 calc R . . C14 C -0.26432(14) 0.30518(11) 0.19190(12) 0.0209(3) Uani 1 1 d . . . H14A H -0.3293 0.3413 0.1768 0.025 Uiso 1 1 calc R . . C15 C -0.20952(14) 0.26504(11) 0.12027(11) 0.0194(3) Uani 1 1 d . . . H15A H -0.2386 0.2732 0.0560 0.023 Uiso 1 1 calc R . . C16 C -0.11287(14) 0.21305(10) 0.14036(10) 0.0156(3) Uani 1 1 d . . . C17 C -0.05817(15) 0.16847(12) 0.05897(10) 0.0185(3) Uani 1 1 d . . . H17A H 0.0316 0.1636 0.0836 0.022 Uiso 1 1 calc R . . C18 C -0.04757(16) 0.23638(13) -0.02460(11) 0.0239(3) Uani 1 1 d . . . H18A H 0.0047 0.3068 -0.0023 0.036 Uiso 1 1 calc R . . H18B H -0.1350 0.2390 -0.0525 0.036 Uiso 1 1 calc R . . H18C H -0.0057 0.2070 -0.0727 0.036 Uiso 1 1 calc R . . C19 C -0.14017(18) 0.05876(12) 0.02289(12) 0.0275(4) Uani 1 1 d . . . H19A H -0.1476 0.0144 0.0760 0.041 Uiso 1 1 calc R . . H19B H -0.0980 0.0298 -0.0253 0.041 Uiso 1 1 calc R . . H19C H -0.2273 0.0619 -0.0051 0.041 Uiso 1 1 calc R . . C20 C 0.43755(14) 0.12856(11) 0.26769(12) 0.0194(3) Uani 1 1 d . . . H20A H 0.4719 0.1092 0.3301 0.023 Uiso 1 1 calc R . . H20B H 0.4770 0.2037 0.2646 0.023 Uiso 1 1 calc R . . C21 C 0.48223(16) 0.06931(13) 0.19078(12) 0.0245(3) Uani 1 1 d . . . H21A H 0.4338 0.0753 0.1283 0.029 Uiso 1 1 calc R . . H21B H 0.5762 0.0996 0.1886 0.029 Uiso 1 1 calc R . . C22 C 0.4962(2) -0.09524(17) 0.13585(15) 0.0438(5) Uani 1 1 d . . . H22A H 0.4799 -0.1680 0.1508 0.066 Uiso 1 1 calc R . . H22B H 0.5891 -0.0677 0.1311 0.066 Uiso 1 1 calc R . . H22C H 0.4444 -0.0909 0.0752 0.066 Uiso 1 1 calc R . . C23 C 0.43343(13) 0.41710(10) 0.28914(10) 0.0138(3) Uani 1 1 d . . . C24 C 0.51744(14) 0.49527(11) 0.24362(11) 0.0183(3) Uani 1 1 d . . . H24A H 0.4863 0.5127 0.1827 0.022 Uiso 1 1 calc R . . C25 C 0.64150(15) 0.54596(12) 0.28496(11) 0.0218(3) Uani 1 1 d . . . H25A H 0.6946 0.5959 0.2512 0.026 Uiso 1 1 calc R . . C26 C 0.69138(15) 0.52582(12) 0.37535(11) 0.0215(3) Uani 1 1 d . . . H26A H 0.7780 0.5601 0.4029 0.026 Uiso 1 1 calc R . . C27 C 0.61164(14) 0.45499(11) 0.42316(11) 0.0187(3) Uani 1 1 d . . . H27A H 0.6434 0.4427 0.4857 0.022 Uiso 1 1 calc R . . C28 C 0.48398(14) 0.39942(10) 0.38317(10) 0.0148(3) Uani 1 1 d . . . C29 C 0.41197(14) 0.33376(11) 0.44665(10) 0.0160(3) Uani 1 1 d . . . H29A H 0.4541 0.3385 0.5101 0.019 Uiso 1 1 calc R . . C30 C 0.26596(13) 0.40653(10) 0.16131(10) 0.0135(3) Uani 1 1 d . . . C31 C 0.19629(14) 0.48219(11) 0.17063(11) 0.0169(3) Uani 1 1 d . . . C32 C 0.17247(16) 0.52193(12) 0.26729(11) 0.0236(3) Uani 1 1 d . . . H32A H 0.1886 0.4715 0.3141 0.028 Uiso 1 1 calc R . . C33 C 0.26872(19) 0.62792(15) 0.30016(14) 0.0380(5) Uani 1 1 d . . . H33A H 0.3582 0.6222 0.2998 0.057 Uiso 1 1 calc R . . H33B H 0.2571 0.6495 0.3647 0.057 Uiso 1 1 calc R . . H33C H 0.2521 0.6796 0.2569 0.057 Uiso 1 1 calc R . . C34 C 0.03268(17) 0.53009(14) 0.26755(13) 0.0315(4) Uani 1 1 d . . . H34A H -0.0281 0.4624 0.2465 0.047 Uiso 1 1 calc R . . H34B H 0.0157 0.5817 0.2243 0.047 Uiso 1 1 calc R . . H34C H 0.0207 0.5515 0.3320 0.047 Uiso 1 1 calc R . . C35 C 0.15342(15) 0.52516(11) 0.08938(11) 0.0196(3) Uani 1 1 d . . . H35A H 0.1062 0.5762 0.0951 0.024 Uiso 1 1 calc R . . C36 C 0.17796(14) 0.49524(11) 0.00068(11) 0.0198(3) Uani 1 1 d . . . H36A H 0.1478 0.5253 -0.0539 0.024 Uiso 1 1 calc R . . C37 C 0.24682(14) 0.42116(11) -0.00803(10) 0.0178(3) Uani 1 1 d . . . H37A H 0.2630 0.4003 -0.0692 0.021 Uiso 1 1 calc R . . C38 C 0.29292(13) 0.37647(10) 0.07125(10) 0.0145(3) Uani 1 1 d . . . C39 C 0.37466(14) 0.29980(11) 0.05868(10) 0.0167(3) Uani 1 1 d . . . H39A H 0.4159 0.2891 0.1231 0.020 Uiso 1 1 calc R . . C40 C 0.48393(16) 0.34073(13) -0.00070(13) 0.0269(4) Uani 1 1 d . . . H40A H 0.5380 0.4082 0.0283 0.040 Uiso 1 1 calc R . . H40B H 0.4459 0.3487 -0.0653 0.040 Uiso 1 1 calc R . . H40C H 0.5379 0.2915 -0.0032 0.040 Uiso 1 1 calc R . . C41 C 0.29021(16) 0.19499(12) 0.01411(12) 0.0235(3) Uani 1 1 d . . . H41A H 0.2204 0.1692 0.0525 0.035 Uiso 1 1 calc R . . H41B H 0.3439 0.1455 0.0116 0.035 Uiso 1 1 calc R . . H41C H 0.2519 0.2028 -0.0504 0.035 Uiso 1 1 calc R . . C42 C 0.25070(15) 0.21359(11) 0.50949(10) 0.0178(3) Uani 1 1 d . . . H42A H 0.1617 0.2200 0.5152 0.021 Uiso 1 1 calc R . . H42B H 0.3080 0.2458 0.5688 0.021 Uiso 1 1 calc R . . C43 C 0.24832(16) 0.09965(12) 0.49761(11) 0.0212(3) Uani 1 1 d . . . H43A H 0.2165 0.0653 0.5535 0.025 Uiso 1 1 calc R . . H43B H 0.1858 0.0667 0.4408 0.025 Uiso 1 1 calc R . . C44 C 0.45838(18) 0.10136(14) 0.57409(13) 0.0324(4) Uani 1 1 d . . . H44A H 0.5417 0.0883 0.5627 0.049 Uiso 1 1 calc R . . H44B H 0.4203 0.0550 0.6204 0.049 Uiso 1 1 calc R . . H44C H 0.4730 0.1738 0.5989 0.049 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 Zn 0.01174(8) 0.01072(8) 0.01323(8) 0.00132(6) 0.00287(6) 0.00306(6) O1 0.0376(7) 0.0305(6) 0.0224(6) 0.0076(5) 0.0105(5) 0.0200(5) O2 0.0336(7) 0.0244(6) 0.0387(7) -0.0044(5) 0.0163(6) 0.0120(5) N1 0.0123(5) 0.0126(5) 0.0134(6) 0.0018(4) 0.0009(4) 0.0031(4) N2 0.0179(6) 0.0151(6) 0.0139(6) 0.0017(4) 0.0040(5) 0.0071(5) N3 0.0142(6) 0.0158(6) 0.0140(6) 0.0013(4) 0.0043(5) 0.0053(5) N4 0.0118(5) 0.0128(5) 0.0168(6) 0.0018(4) 0.0025(5) 0.0046(4) C1 0.0189(7) 0.0146(7) 0.0187(7) 0.0025(5) 0.0057(6) 0.0079(6) C2 0.0169(7) 0.0128(6) 0.0122(6) 0.0009(5) 0.0033(5) 0.0033(5) C3 0.0225(8) 0.0150(7) 0.0194(7) 0.0014(5) 0.0054(6) 0.0072(6) C4 0.0248(8) 0.0130(7) 0.0226(8) 0.0015(6) 0.0058(6) 0.0017(6) C5 0.0170(7) 0.0194(7) 0.0178(7) 0.0013(6) 0.0040(6) -0.0010(6) C6 0.0156(7) 0.0176(7) 0.0156(7) 0.0018(5) 0.0032(5) 0.0042(6) C7 0.0160(7) 0.0134(6) 0.0098(6) 0.0010(5) 0.0028(5) 0.0039(5) C8 0.0105(6) 0.0100(6) 0.0208(7) 0.0013(5) 0.0027(5) 0.0014(5) C9 0.0142(7) 0.0144(6) 0.0204(7) 0.0001(5) 0.0025(6) 0.0028(5) C10 0.0190(7) 0.0220(7) 0.0192(7) -0.0017(6) 0.0043(6) 0.0083(6) C11 0.0238(8) 0.0283(8) 0.0251(8) -0.0063(7) 0.0014(7) 0.0055(7) C12 0.0280(9) 0.0305(9) 0.0254(9) 0.0032(7) 0.0089(7) 0.0056(7) C13 0.0162(7) 0.0180(7) 0.0272(8) -0.0023(6) 0.0061(6) 0.0061(6) C14 0.0145(7) 0.0185(7) 0.0309(9) 0.0025(6) 0.0018(6) 0.0071(6) C15 0.0160(7) 0.0188(7) 0.0229(8) 0.0056(6) 0.0009(6) 0.0040(6) C16 0.0126(7) 0.0128(6) 0.0205(7) 0.0023(5) 0.0039(6) 0.0009(5) C17 0.0170(7) 0.0228(7) 0.0174(7) 0.0044(6) 0.0032(6) 0.0072(6) C18 0.0230(8) 0.0264(8) 0.0217(8) 0.0065(6) 0.0051(6) 0.0037(6) C19 0.0405(10) 0.0191(8) 0.0226(8) 0.0001(6) 0.0065(7) 0.0063(7) C20 0.0145(7) 0.0168(7) 0.0288(8) 0.0023(6) 0.0065(6) 0.0056(6) C21 0.0223(8) 0.0310(9) 0.0255(8) 0.0066(7) 0.0095(7) 0.0129(7) C22 0.0337(10) 0.0512(12) 0.0483(12) -0.0261(10) 0.0012(9) 0.0220(9) C23 0.0139(6) 0.0121(6) 0.0162(7) -0.0022(5) 0.0028(5) 0.0047(5) C24 0.0183(7) 0.0166(7) 0.0184(7) 0.0006(5) 0.0023(6) 0.0020(6) C25 0.0191(7) 0.0181(7) 0.0253(8) -0.0024(6) 0.0064(6) -0.0013(6) C26 0.0135(7) 0.0219(7) 0.0262(8) -0.0079(6) 0.0008(6) 0.0016(6) C27 0.0168(7) 0.0210(7) 0.0184(7) -0.0051(6) -0.0008(6) 0.0076(6) C28 0.0153(7) 0.0140(6) 0.0159(7) -0.0022(5) 0.0015(5) 0.0059(5) C29 0.0190(7) 0.0177(7) 0.0133(7) -0.0010(5) 0.0001(5) 0.0099(6) C30 0.0111(6) 0.0112(6) 0.0164(7) 0.0033(5) 0.0013(5) -0.0004(5) C31 0.0164(7) 0.0134(6) 0.0203(7) 0.0017(5) 0.0028(6) 0.0027(5) C32 0.0304(9) 0.0224(8) 0.0221(8) -0.0001(6) 0.0047(7) 0.0145(7) C33 0.0308(10) 0.0398(11) 0.0405(11) -0.0192(9) -0.0013(8) 0.0110(8) C34 0.0304(9) 0.0311(9) 0.0347(10) -0.0038(7) 0.0110(8) 0.0091(7) C35 0.0183(7) 0.0152(7) 0.0258(8) 0.0039(6) 0.0013(6) 0.0058(6) C36 0.0165(7) 0.0196(7) 0.0216(8) 0.0087(6) -0.0012(6) 0.0019(6) C37 0.0158(7) 0.0203(7) 0.0157(7) 0.0029(5) 0.0024(6) 0.0013(6) C38 0.0125(6) 0.0133(6) 0.0168(7) 0.0018(5) 0.0023(5) 0.0012(5) C39 0.0167(7) 0.0193(7) 0.0149(7) 0.0011(5) 0.0025(6) 0.0062(6) C40 0.0189(8) 0.0276(8) 0.0362(10) 0.0042(7) 0.0109(7) 0.0060(7) C41 0.0218(8) 0.0197(7) 0.0300(9) -0.0016(6) 0.0074(7) 0.0063(6) C42 0.0207(7) 0.0223(7) 0.0124(7) 0.0040(5) 0.0040(6) 0.0079(6) C43 0.0272(8) 0.0205(7) 0.0165(7) 0.0043(6) 0.0050(6) 0.0055(6) C44 0.0319(9) 0.0337(9) 0.0363(10) 0.0056(8) 0.0033(8) 0.0173(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 Zn N4 1.9649(12) . ? Zn N1 1.9667(11) . ? Zn N3 2.0342(12) . ? Zn N2 2.0681(12) . ? O1 C44 1.417(2) . ? O1 C43 1.4197(19) . ? O2 C21 1.410(2) . ? O2 C22 1.417(2) . ? N1 C23 1.3619(18) . ? N1 C30 1.4370(18) . ? N2 C29 1.2897(19) . ? N2 C42 1.4700(18) . ? N3 C1 1.2875(18) . ? N3 C20 1.4787(18) . ? N4 C7 1.3674(17) . ? N4 C8 1.4431(17) . ? C1 C2 1.446(2) . ? C1 H1A 0.9500 . ? C2 C3 1.4124(19) . ? C2 C7 1.4358(19) . ? C3 C4 1.372(2) . ? C3 H3A 0.9500 . ? C4 C5 1.397(2) . ? C4 H4A 0.9500 . ? C5 C6 1.373(2) . ? C5 H5A 0.9500 . ? C6 C7 1.4285(19) . ? C6 H6A 0.9500 . ? C8 C16 1.411(2) . ? C8 C9 1.411(2) . ? C9 C13 1.396(2) . ? C9 C10 1.516(2) . ? C10 C11 1.532(2) . ? C10 C12 1.534(2) . ? C10 H10A 1.0000 . ? 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 C14 1.378(2) . ? C13 H13A 0.9500 . ? C14 C15 1.386(2) . ? C14 H14A 0.9500 . ? C15 C16 1.393(2) . ? C15 H15A 0.9500 . ? C16 C17 1.520(2) . ? C17 C18 1.526(2) . ? C17 C19 1.533(2) . ? C17 H17A 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.512(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.431(2) . ? C23 C28 1.433(2) . ? C24 C25 1.373(2) . ? C24 H24A 0.9500 . ? C25 C26 1.396(2) . ? C25 H25A 0.9500 . ? C26 C27 1.371(2) . ? C26 H26A 0.9500 . ? C27 C28 1.414(2) . ? C27 H27A 0.9500 . ? C28 C29 1.442(2) . ? C29 H29A 0.9500 . ? C30 C31 1.408(2) . ? C30 C38 1.409(2) . ? C31 C35 1.393(2) . ? C31 C32 1.524(2) . ? C32 C34 1.527(2) . ? C32 C33 1.538(2) . ? C32 H32A 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.381(2) . ? C35 H35A 0.9500 . ? C36 C37 1.383(2) . ? C36 H36A 0.9500 . ? C37 C38 1.395(2) . ? C37 H37A 0.9500 . ? C38 C39 1.5211(19) . ? C39 C41 1.522(2) . ? C39 C40 1.530(2) . ? C39 H39A 1.0000 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.515(2) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 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 N4 Zn N1 132.40(5) . . ? N4 Zn N3 95.81(5) . . ? N1 Zn N3 113.45(5) . . ? N4 Zn N2 119.45(5) . . ? N1 Zn N2 94.19(5) . . ? N3 Zn N2 97.16(5) . . ? C44 O1 C43 113.24(12) . . ? C21 O2 C22 111.93(15) . . ? C23 N1 C30 115.29(11) . . ? C23 N1 Zn 122.36(9) . . ? C30 N1 Zn 122.21(9) . . ? C29 N2 C42 115.63(12) . . ? C29 N2 Zn 117.96(10) . . ? C42 N2 Zn 125.20(9) . . ? C1 N3 C20 117.37(12) . . ? C1 N3 Zn 120.17(10) . . ? C20 N3 Zn 120.81(9) . . ? C7 N4 C8 116.35(11) . . ? C7 N4 Zn 122.61(9) . . ? C8 N4 Zn 120.99(9) . . ? N3 C1 C2 127.41(13) . . ? N3 C1 H1A 116.3 . . ? C2 C1 H1A 116.3 . . ? C3 C2 C7 119.69(13) . . ? C3 C2 C1 113.69(12) . . ? C7 C2 C1 126.61(12) . . ? C4 C3 C2 123.02(14) . . ? C4 C3 H3A 118.5 . . ? C2 C3 H3A 118.5 . . ? C3 C4 C5 117.67(13) . . ? C3 C4 H4A 121.2 . . ? C5 C4 H4A 121.2 . . ? C6 C5 C4 121.47(14) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C7 122.63(13) . . ? C5 C6 H6A 118.7 . . ? C7 C6 H6A 118.7 . . ? N4 C7 C6 121.49(12) . . ? N4 C7 C2 123.02(12) . . ? C6 C7 C2 115.49(12) . . ? C16 C8 C9 119.92(13) . . ? C16 C8 N4 119.24(12) . . ? C9 C8 N4 120.84(13) . . ? C13 C9 C8 118.92(14) . . ? C13 C9 C10 118.72(13) . . ? C8 C9 C10 122.37(13) . . ? C9 C10 C11 110.68(13) . . ? C9 C10 C12 111.92(13) . . ? C11 C10 C12 109.88(13) . . ? C9 C10 H10A 108.1 . . ? C11 C10 H10A 108.1 . . ? C12 C10 H10A 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C9 121.43(14) . . ? C14 C13 H13A 119.3 . . ? C9 C13 H13A 119.3 . . ? C13 C14 C15 119.36(14) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C14 C15 C16 121.55(14) . . ? C14 C15 H15A 119.2 . . ? C16 C15 H15A 119.2 . . ? C15 C16 C8 118.79(13) . . ? C15 C16 C17 119.39(13) . . ? C8 C16 C17 121.81(12) . . ? C16 C17 C18 112.93(12) . . ? C16 C17 C19 111.51(12) . . ? C18 C17 C19 108.79(13) . . ? C16 C17 H17A 107.8 . . ? C18 C17 H17A 107.8 . . ? C19 C17 H17A 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 C21 115.75(13) . . ? N3 C20 H20A 108.3 . . ? C21 C20 H20A 108.3 . . ? N3 C20 H20B 108.3 . . ? C21 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? O2 C21 C20 110.31(13) . . ? O2 C21 H21A 109.6 . . ? C20 C21 H21A 109.6 . . ? O2 C21 H21B 109.6 . . ? C20 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 C24 121.54(13) . . ? N1 C23 C28 122.73(12) . . ? C24 C23 C28 115.73(13) . . ? C25 C24 C23 122.24(14) . . ? C25 C24 H24A 118.9 . . ? C23 C24 H24A 118.9 . . ? C24 C25 C26 121.53(14) . . ? C24 C25 H25A 119.2 . . ? C26 C25 H25A 119.2 . . ? C27 C26 C25 117.96(14) . . ? C27 C26 H26A 121.0 . . ? C25 C26 H26A 121.0 . . ? C26 C27 C28 122.71(14) . . ? C26 C27 H27A 118.6 . . ? C28 C27 H27A 118.6 . . ? C27 C28 C23 119.71(13) . . ? C27 C28 C29 114.57(13) . . ? C23 C28 C29 125.55(13) . . ? N2 C29 C28 128.68(13) . . ? N2 C29 H29A 115.7 . . ? C28 C29 H29A 115.7 . . ? C31 C30 C38 120.13(13) . . ? C31 C30 N1 118.94(12) . . ? C38 C30 N1 120.89(12) . . ? C35 C31 C30 118.81(13) . . ? C35 C31 C32 119.27(13) . . ? C30 C31 C32 121.85(13) . . ? C31 C32 C34 112.58(14) . . ? C31 C32 C33 110.55(14) . . ? C34 C32 C33 109.88(13) . . ? C31 C32 H32A 107.9 . . ? C34 C32 H32A 107.9 . . ? C33 C32 H32A 107.9 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 C31 121.46(14) . . ? C36 C35 H35A 119.3 . . ? C31 C35 H35A 119.3 . . ? C35 C36 C37 119.49(14) . . ? C35 C36 H36A 120.3 . . ? C37 C36 H36A 120.3 . . ? C36 C37 C38 121.26(14) . . ? C36 C37 H37A 119.4 . . ? C38 C37 H37A 119.4 . . ? C37 C38 C30 118.83(13) . . ? C37 C38 C39 119.26(13) . . ? C30 C38 C39 121.87(13) . . ? C38 C39 C41 111.13(12) . . ? C38 C39 C40 112.08(12) . . ? C41 C39 C40 109.86(13) . . ? C38 C39 H39A 107.9 . . ? C41 C39 H39A 107.9 . . ? C40 C39 H39A 107.9 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N2 C42 C43 111.70(12) . . ? N2 C42 H42A 109.3 . . ? C43 C42 H42A 109.3 . . ? N2 C42 H42B 109.3 . . ? C43 C42 H42B 109.3 . . ? H42A C42 H42B 107.9 . . ? O1 C43 C42 113.43(13) . . ? O1 C43 H43A 108.9 . . ? C42 C43 H43A 108.9 . . ? O1 C43 H43B 108.9 . . ? C42 C43 H43B 108.9 . . ? H43A C43 H43B 107.7 . . ? O1 C44 H44A 109.5 . . ? O1 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O1 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Zn N1 C23 166.90(9) . . . . ? N3 Zn N1 C23 -70.04(11) . . . . ? N2 Zn N1 C23 29.64(11) . . . . ? N4 Zn N1 C30 -17.68(13) . . . . ? N3 Zn N1 C30 105.38(10) . . . . ? N2 Zn N1 C30 -154.94(10) . . . . ? N4 Zn N2 C29 -171.21(10) . . . . ? N1 Zn N2 C29 -26.35(11) . . . . ? N3 Zn N2 C29 87.94(11) . . . . ? N4 Zn N2 C42 21.98(12) . . . . ? N1 Zn N2 C42 166.84(11) . . . . ? N3 Zn N2 C42 -78.87(11) . . . . ? N4 Zn N3 C1 -19.92(12) . . . . ? N1 Zn N3 C1 -161.45(11) . . . . ? N2 Zn N3 C1 100.80(11) . . . . ? N4 Zn N3 C20 175.07(11) . . . . ? N1 Zn N3 C20 33.54(12) . . . . ? N2 Zn N3 C20 -64.20(11) . . . . ? N1 Zn N4 C7 150.77(10) . . . . ? N3 Zn N4 C7 21.38(11) . . . . ? N2 Zn N4 C7 -80.25(11) . . . . ? N1 Zn N4 C8 -32.12(13) . . . . ? N3 Zn N4 C8 -161.51(10) . . . . ? N2 Zn N4 C8 96.86(11) . . . . ? C20 N3 C1 C2 176.34(14) . . . . ? Zn N3 C1 C2 10.8(2) . . . . ? N3 C1 C2 C3 -176.87(14) . . . . ? N3 C1 C2 C7 4.2(2) . . . . ? C7 C2 C3 C4 0.9(2) . . . . ? C1 C2 C3 C4 -178.10(14) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C3 C4 C5 C6 -1.3(2) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? C8 N4 C7 C6 -10.84(19) . . . . ? Zn N4 C7 C6 166.39(10) . . . . ? C8 N4 C7 C2 169.26(12) . . . . ? Zn N4 C7 C2 -13.50(18) . . . . ? C5 C6 C7 N4 -178.62(13) . . . . ? C5 C6 C7 C2 1.3(2) . . . . ? C3 C2 C7 N4 178.08(13) . . . . ? C1 C2 C7 N4 -3.1(2) . . . . ? C3 C2 C7 C6 -1.82(19) . . . . ? C1 C2 C7 C6 177.03(13) . . . . ? C7 N4 C8 C16 -88.33(15) . . . . ? Zn N4 C8 C16 94.39(13) . . . . ? C7 N4 C8 C9 91.97(16) . . . . ? Zn N4 C8 C9 -85.32(14) . . . . ? C16 C8 C9 C13 -2.2(2) . . . . ? N4 C8 C9 C13 177.46(12) . . . . ? C16 C8 C9 C10 177.35(13) . . . . ? N4 C8 C9 C10 -2.9(2) . . . . ? C13 C9 C10 C11 -69.64(17) . . . . ? C8 C9 C10 C11 110.76(15) . . . . ? C13 C9 C10 C12 53.30(18) . . . . ? C8 C9 C10 C12 -126.30(15) . . . . ? C8 C9 C13 C14 1.0(2) . . . . ? C10 C9 C13 C14 -178.57(14) . . . . ? C9 C13 C14 C15 0.5(2) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C14 C15 C16 C8 -0.3(2) . . . . ? C14 C15 C16 C17 178.67(13) . . . . ? C9 C8 C16 C15 1.9(2) . . . . ? N4 C8 C16 C15 -177.83(12) . . . . ? C9 C8 C16 C17 -177.06(13) . . . . ? N4 C8 C16 C17 3.23(19) . . . . ? C15 C16 C17 C18 36.08(19) . . . . ? C8 C16 C17 C18 -144.99(14) . . . . ? C15 C16 C17 C19 -86.79(16) . . . . ? C8 C16 C17 C19 92.15(16) . . . . ? C1 N3 C20 C21 56.15(18) . . . . ? Zn N3 C20 C21 -138.44(11) . . . . ? C22 O2 C21 C20 177.46(14) . . . . ? N3 C20 C21 O2 -74.94(17) . . . . ? C30 N1 C23 C24 -13.12(18) . . . . ? Zn N1 C23 C24 162.60(10) . . . . ? C30 N1 C23 C28 166.52(12) . . . . ? Zn N1 C23 C28 -17.76(18) . . . . ? N1 C23 C24 C25 -176.69(13) . . . . ? C28 C23 C24 C25 3.6(2) . . . . ? C23 C24 C25 C26 -1.8(2) . . . . ? C24 C25 C26 C27 -1.3(2) . . . . ? C25 C26 C27 C28 2.5(2) . . . . ? C26 C27 C28 C23 -0.5(2) . . . . ? C26 C27 C28 C29 -175.95(13) . . . . ? N1 C23 C28 C27 177.82(12) . . . . ? C24 C23 C28 C27 -2.52(19) . . . . ? N1 C23 C28 C29 -7.2(2) . . . . ? C24 C23 C28 C29 172.44(13) . . . . ? C42 N2 C29 C28 -179.85(13) . . . . ? Zn N2 C29 C28 12.09(19) . . . . ? C27 C28 C29 N2 -175.04(14) . . . . ? C23 C28 C29 N2 9.8(2) . . . . ? C23 N1 C30 C31 -88.34(15) . . . . ? Zn N1 C30 C31 95.94(13) . . . . ? C23 N1 C30 C38 89.25(15) . . . . ? Zn N1 C30 C38 -86.48(14) . . . . ? C38 C30 C31 C35 0.9(2) . . . . ? N1 C30 C31 C35 178.51(12) . . . . ? C38 C30 C31 C32 -176.06(13) . . . . ? N1 C30 C31 C32 1.5(2) . . . . ? C35 C31 C32 C34 47.04(19) . . . . ? C30 C31 C32 C34 -136.01(15) . . . . ? C35 C31 C32 C33 -76.27(18) . . . . ? C30 C31 C32 C33 100.68(17) . . . . ? C30 C31 C35 C36 -0.1(2) . . . . ? C32 C31 C35 C36 176.96(14) . . . . ? C31 C35 C36 C37 -0.1(2) . . . . ? C35 C36 C37 C38 -0.5(2) . . . . ? C36 C37 C38 C30 1.3(2) . . . . ? C36 C37 C38 C39 -176.60(13) . . . . ? C31 C30 C38 C37 -1.5(2) . . . . ? N1 C30 C38 C37 -179.04(12) . . . . ? C31 C30 C38 C39 176.33(13) . . . . ? N1 C30 C38 C39 -1.2(2) . . . . ? C37 C38 C39 C41 -75.09(16) . . . . ? C30 C38 C39 C41 107.11(15) . . . . ? C37 C38 C39 C40 48.27(18) . . . . ? C30 C38 C39 C40 -129.53(14) . . . . ? C29 N2 C42 C43 -109.36(14) . . . . ? Zn N2 C42 C43 57.72(15) . . . . ? C44 O1 C43 C42 74.58(16) . . . . ? N2 C42 C43 O1 58.22(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.385 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 928701'