# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Arjan Kleij' _publ_contact_author_email AKLEIJ@ICIQ.ES _publ_section_title ; Assembly of unusual Zn-cluster compounds based on pyridinealcohol platforms ; loop_ _publ_author_name 'Arjan Kleij' 'Daniele Anselmo' 'Jordi Benet-Buchholz' 'Eduardo C. Escudero-Adan' # Attachment 'awk388p21c.cif' data_awk388p21c _database_code_depnum_ccdc_archive 'CCDC 717122' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22.50 N2.50 O8 Zn2' _chemical_formula_weight 544.64 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.1997(5) _cell_length_b 15.3812(5) _cell_length_c 16.6760(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.4030(10) _cell_angle_gamma 90.00 _cell_volume 4339.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7057 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 38.18 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 2.261 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7039 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 97739 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 39.93 _reflns_number_total 25349 _reflns_number_gt 18568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2008.6-1' _computing_cell_refinement 'Bruker APEX2 v2008.6-1' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-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^)+(0.0372P)^2^+1.0995P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 25349 _refine_ls_number_parameters 575 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.209205(8) 0.420531(10) 0.082699(8) 0.01054(3) Uani 1 1 d . . . C1 C 0.09716(7) 0.47795(9) -0.08605(7) 0.0136(2) Uani 1 1 d . . . N1 N 0.12297(6) 0.49221(7) -0.00522(6) 0.01164(17) Uani 1 1 d . . . Zn2 Zn 0.225231(8) 0.486385(10) 0.267095(8) 0.01059(3) Uani 1 1 d . . . C2 C 0.04468(8) 0.53414(10) -0.13289(8) 0.0171(2) Uani 1 1 d . . . H2 H 0.0275 0.5231 -0.1894 0.021 Uiso 1 1 calc R . . O2 O 0.20371(6) 0.41060(7) -0.14182(6) 0.01700(18) Uani 1 1 d . . . H2A H 0.2369 0.4159 -0.0985 0.025 Uiso 1 1 calc R . . N2 N 0.44599(6) 0.42186(8) 0.25490(6) 0.01262(17) Uani 1 1 d . . . Zn3 Zn 0.375451(8) 0.513987(10) 0.186860(8) 0.01059(3) Uani 1 1 d . . . C3 C 0.01725(8) 0.60677(10) -0.09687(8) 0.0179(2) Uani 1 1 d . . . H3 H -0.0187 0.6459 -0.1283 0.021 Uiso 1 1 calc R . . O3 O 0.13093(6) 0.26134(7) 0.16885(6) 0.02021(19) Uani 1 1 d . . . N3 N 0.28477(6) 0.42791(7) 0.37290(6) 0.01179(17) Uani 1 1 d . . . Zn4 Zn 0.296634(8) 0.686598(10) 0.246953(9) 0.01130(3) Uani 1 1 d . . . C4 C 0.04311(7) 0.62107(9) -0.01456(8) 0.0156(2) Uani 1 1 d . . . H4 H 0.0252 0.6701 0.0116 0.019 Uiso 1 1 calc R . . O4 O 0.17896(6) 0.29813(7) 0.05742(6) 0.01706(18) Uani 1 1 d . . . N4 N 0.26099(6) 0.78163(7) 0.14812(6) 0.01197(17) Uani 1 1 d . . . C5 C 0.09610(7) 0.56195(8) 0.02931(7) 0.01189(19) Uani 1 1 d . . . O5 O 0.29419(5) 0.41091(6) 0.18713(5) 0.01124(15) Uani 1 1 d . . . C6 C 0.12663(8) 0.39788(9) -0.12249(8) 0.0165(2) Uani 1 1 d . . . H6A H 0.1285 0.3491 -0.0835 0.020 Uiso 1 1 calc R . . H6B H 0.0892 0.3820 -0.1727 0.020 Uiso 1 1 calc R . . O6 O 0.49220(6) 0.58086(7) 0.23073(6) 0.01626(17) Uani 1 1 d . . . C7 C 0.14957(7) 0.24460(9) 0.10206(8) 0.0141(2) Uani 1 1 d . . . O7 O 0.15378(5) 0.37093(7) 0.28601(6) 0.01458(16) Uani 1 1 d . . . C8 C 0.13437(11) 0.15345(11) 0.06954(10) 0.0268(3) Uani 1 1 d . . . H8A H 0.1416 0.1122 0.1151 0.040 Uiso 1 1 calc R . . H8B H 0.1715 0.1397 0.0332 0.040 Uiso 1 1 calc R . . H8C H 0.0801 0.1493 0.0392 0.040 Uiso 1 1 calc R . . O8 O 0.14904(6) 0.56572(7) 0.31477(6) 0.01518(17) Uani 1 1 d . . . C9 C 0.41203(7) 0.34490(9) 0.26385(7) 0.0129(2) Uani 1 1 d . . . O9 O 0.19299(6) 0.69708(7) 0.28474(6) 0.01708(18) Uani 1 1 d . . . C10 C 0.45003(8) 0.28255(10) 0.31713(9) 0.0183(2) Uani 1 1 d . . . H10 H 0.4258 0.2280 0.3231 0.022 Uiso 1 1 calc R . . O10 O 0.32328(6) 0.62431(7) 0.15221(6) 0.01637(17) Uani 1 1 d . . . C11 C 0.52445(9) 0.30193(11) 0.36145(9) 0.0227(3) Uani 1 1 d . . . H11 H 0.5515 0.2606 0.3987 0.027 Uiso 1 1 calc R . . O11 O 0.36210(6) 0.76276(7) 0.32709(6) 0.01817(18) Uani 1 1 d . . . C12 C 0.55907(8) 0.38145(11) 0.35142(9) 0.0203(3) Uani 1 1 d . . . H12 H 0.6099 0.3953 0.3814 0.024 Uiso 1 1 calc R . . O12 O 0.48330(6) 0.70517(7) 0.33384(6) 0.01885(19) Uani 1 1 d . . . C13 C 0.51787(7) 0.44054(9) 0.29659(8) 0.0144(2) Uani 1 1 d . . . O13 O 0.19550(9) 0.98389(8) 0.22517(7) 0.0318(3) Uani 1 1 d . . . H13 H 0.1990 1.0071 0.2713 0.048 Uiso 1 1 calc R . . C14 C 0.33194(7) 0.33140(9) 0.21020(8) 0.0141(2) Uani 1 1 d . . . H14A H 0.3387 0.2988 0.1607 0.017 Uiso 1 1 calc R . . H14B H 0.2983 0.2962 0.2400 0.017 Uiso 1 1 calc R . . O14 O 0.17023(6) 0.50492(7) 0.15401(6) 0.01637(18) Uani 1 1 d . . . C15 C 0.55082(7) 0.52815(10) 0.27843(8) 0.0175(2) Uani 1 1 d . . . H15A H 0.5716 0.5582 0.3303 0.021 Uiso 1 1 calc R . . H15B H 0.5952 0.5195 0.2489 0.021 Uiso 1 1 calc R . . O15 O 0.29046(5) 0.43012(7) 0.00674(6) 0.01711(18) Uani 1 1 d . . . C16 C 0.26173(7) 0.35147(9) 0.39902(7) 0.0130(2) Uani 1 1 d . . . O16 O 0.40371(5) 0.48739(7) 0.07335(6) 0.01414(16) Uani 1 1 d . . . C17 C 0.30475(8) 0.31024(9) 0.46717(8) 0.0168(2) Uani 1 1 d . . . H17 H 0.2886 0.2554 0.4846 0.020 Uiso 1 1 calc R . . O17 O 0.32846(5) 0.56394(6) 0.29524(5) 0.01154(15) Uani 1 1 d . . . C18 C 0.37191(8) 0.35138(10) 0.50899(8) 0.0186(2) Uani 1 1 d . . . H18 H 0.4020 0.3253 0.5562 0.022 Uiso 1 1 calc R . . C19 C 0.39476(7) 0.43095(10) 0.48135(8) 0.0161(2) Uani 1 1 d . . . H19 H 0.4403 0.4600 0.5096 0.019 Uiso 1 1 calc R . . C20 C 0.35007(7) 0.46751(9) 0.41182(7) 0.01209(19) Uani 1 1 d . . . C21 C 0.18706(8) 0.31365(9) 0.35051(8) 0.0149(2) Uani 1 1 d . . . H21A H 0.1989 0.2569 0.3274 0.018 Uiso 1 1 calc R . . H21B H 0.1483 0.3037 0.3868 0.018 Uiso 1 1 calc R . . C22 C 0.36905(7) 0.55316(9) 0.37547(7) 0.0129(2) Uani 1 1 d . . . H22A H 0.3549 0.6013 0.4096 0.016 Uiso 1 1 calc R . . H22B H 0.4266 0.5564 0.3760 0.016 Uiso 1 1 calc R . . C23 C 0.14333(7) 0.64736(9) 0.30814(8) 0.0147(2) Uani 1 1 d . . . C24 C 0.07118(9) 0.68974(11) 0.33054(11) 0.0264(3) Uani 1 1 d . . . H24A H 0.0372 0.6451 0.3482 0.040 Uiso 1 1 calc R . . H24B H 0.0419 0.7204 0.2830 0.040 Uiso 1 1 calc R . . H24C H 0.0875 0.7313 0.3750 0.040 Uiso 1 1 calc R . . C25 C 0.27010(7) 0.74948(9) 0.07567(7) 0.01223(19) Uani 1 1 d . . . C26 C 0.25272(8) 0.79775(10) 0.00381(8) 0.0171(2) Uani 1 1 d . . . H26 H 0.2596 0.7733 -0.0468 0.021 Uiso 1 1 calc R . . C27 C 0.22536(9) 0.88169(10) 0.00781(8) 0.0194(2) Uani 1 1 d . . . H27 H 0.2131 0.9160 -0.0402 0.023 Uiso 1 1 calc R . . C28 C 0.21590(8) 0.91543(9) 0.08258(8) 0.0176(2) Uani 1 1 d . . . H28 H 0.1974 0.9732 0.0864 0.021 Uiso 1 1 calc R . . C29 C 0.23379(7) 0.86388(9) 0.15184(8) 0.0139(2) Uani 1 1 d . . . C30 C 0.30108(7) 0.65748(8) 0.07426(7) 0.0128(2) Uani 1 1 d . . . H30A H 0.2596 0.6200 0.0430 0.015 Uiso 1 1 calc R . . H30B H 0.3472 0.6569 0.0463 0.015 Uiso 1 1 calc R . . C31 C 0.22481(9) 0.89768(10) 0.23439(8) 0.0193(2) Uani 1 1 d . . . H31A H 0.1877 0.8604 0.2579 0.023 Uiso 1 1 calc R . . H31B H 0.2766 0.8969 0.2717 0.023 Uiso 1 1 calc R . . C32 C 0.43568(8) 0.75785(9) 0.35523(7) 0.0145(2) Uani 1 1 d . . . C33 C 0.46766(9) 0.82289(11) 0.42073(9) 0.0234(3) Uani 1 1 d . . . H33A H 0.5031 0.7933 0.4650 0.035 Uiso 1 1 calc R . . H33B H 0.4237 0.8493 0.4421 0.035 Uiso 1 1 calc R . . H33C H 0.4970 0.8683 0.3976 0.035 Uiso 1 1 calc R . . C34 C 0.12448(7) 0.57456(8) 0.11982(7) 0.01249(19) Uani 1 1 d . . . H34A H 0.1560 0.6286 0.1290 0.015 Uiso 1 1 calc R . . H34B H 0.0783 0.5810 0.1471 0.015 Uiso 1 1 calc R . . C35 C 0.36179(7) 0.45520(9) 0.01161(7) 0.01226(19) Uani 1 1 d . . . C36 C 0.39618(8) 0.44528(11) -0.06507(8) 0.0207(3) Uani 1 1 d . . . H36A H 0.3693 0.4851 -0.1070 0.031 Uiso 1 1 calc R . . H36B H 0.3889 0.3853 -0.0848 0.031 Uiso 1 1 calc R . . H36C H 0.4527 0.4590 -0.0532 0.031 Uiso 1 1 calc R . . C1S C 0.01299(9) 0.85775(14) 0.12796(11) 0.0307(4) Uani 1 1 d . . . C2S C 0.00345(11) 0.95160(13) 0.12910(11) 0.0308(3) Uani 1 1 d . . . H2SA H -0.0057 0.9738 0.0731 0.046 Uiso 1 1 calc R . . H2SB H 0.0514 0.9781 0.1602 0.046 Uiso 1 1 calc R . . H2SC H -0.0418 0.9662 0.1548 0.046 Uiso 1 1 calc R . . N1S N 0.02000(11) 0.78394(14) 0.12633(13) 0.0457(5) 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 Zn1 0.01220(6) 0.00900(7) 0.01074(5) -0.00026(4) 0.00288(4) 0.00034(4) C1 0.0144(5) 0.0140(6) 0.0122(4) 0.0002(4) 0.0018(4) -0.0024(4) N1 0.0128(4) 0.0109(5) 0.0113(4) 0.0003(3) 0.0022(3) -0.0006(3) Zn2 0.01199(6) 0.01014(7) 0.00978(5) 0.00058(5) 0.00233(4) 0.00022(4) C2 0.0172(5) 0.0195(7) 0.0135(5) 0.0021(4) -0.0001(4) -0.0008(4) O2 0.0182(4) 0.0195(5) 0.0137(4) -0.0019(3) 0.0038(3) -0.0005(3) N2 0.0125(4) 0.0128(5) 0.0129(4) 0.0004(3) 0.0032(3) 0.0026(3) Zn3 0.01170(5) 0.00906(7) 0.01118(6) 0.00074(5) 0.00251(4) 0.00100(4) C3 0.0159(5) 0.0185(7) 0.0180(5) 0.0052(5) 0.0001(4) 0.0015(4) O3 0.0262(5) 0.0174(5) 0.0180(4) -0.0037(4) 0.0066(4) -0.0028(4) N3 0.0126(4) 0.0118(5) 0.0111(4) 0.0014(3) 0.0026(3) -0.0004(3) Zn4 0.01398(6) 0.00922(7) 0.01102(6) 0.00011(5) 0.00314(4) 0.00056(5) C4 0.0152(5) 0.0138(6) 0.0175(5) 0.0022(4) 0.0020(4) 0.0022(4) O4 0.0233(4) 0.0095(4) 0.0194(4) -0.0005(3) 0.0064(3) -0.0018(3) N4 0.0135(4) 0.0106(5) 0.0122(4) 0.0008(3) 0.0033(3) 0.0003(3) C5 0.0110(4) 0.0109(5) 0.0136(4) 0.0010(4) 0.0018(3) -0.0007(3) O5 0.0126(3) 0.0082(4) 0.0130(3) 0.0010(3) 0.0025(3) 0.0019(3) C6 0.0203(5) 0.0147(6) 0.0151(5) -0.0019(4) 0.0044(4) -0.0021(4) O6 0.0160(4) 0.0158(5) 0.0165(4) 0.0011(3) 0.0015(3) -0.0007(3) C7 0.0150(5) 0.0109(6) 0.0157(5) -0.0003(4) 0.0013(4) 0.0012(4) O7 0.0165(4) 0.0125(4) 0.0145(4) 0.0011(3) 0.0018(3) -0.0008(3) C8 0.0451(9) 0.0119(7) 0.0268(7) -0.0036(5) 0.0158(7) -0.0060(6) O8 0.0181(4) 0.0118(4) 0.0172(4) -0.0010(3) 0.0073(3) 0.0007(3) C9 0.0147(5) 0.0118(6) 0.0130(5) 0.0012(4) 0.0044(4) 0.0039(4) O9 0.0182(4) 0.0137(5) 0.0214(4) 0.0004(3) 0.0090(3) 0.0012(3) C10 0.0194(5) 0.0160(6) 0.0202(6) 0.0060(5) 0.0049(4) 0.0053(4) O10 0.0262(5) 0.0123(5) 0.0113(4) 0.0021(3) 0.0054(3) 0.0065(3) C11 0.0197(6) 0.0241(8) 0.0235(6) 0.0095(5) 0.0016(5) 0.0082(5) O11 0.0185(4) 0.0146(5) 0.0198(4) -0.0025(4) -0.0008(3) -0.0012(3) C12 0.0143(5) 0.0250(8) 0.0207(6) 0.0036(5) 0.0004(4) 0.0053(5) O12 0.0190(4) 0.0171(5) 0.0204(4) -0.0031(4) 0.0035(3) -0.0011(3) C13 0.0123(4) 0.0173(6) 0.0137(5) 0.0001(4) 0.0027(4) 0.0028(4) O13 0.0578(8) 0.0171(6) 0.0189(5) -0.0020(4) 0.0030(5) 0.0168(5) C14 0.0164(5) 0.0092(5) 0.0163(5) 0.0005(4) 0.0024(4) 0.0021(4) O14 0.0208(4) 0.0161(5) 0.0112(4) -0.0008(3) 0.0000(3) 0.0089(3) C15 0.0132(5) 0.0203(7) 0.0189(5) 0.0001(5) 0.0023(4) -0.0012(4) O15 0.0132(4) 0.0253(6) 0.0135(4) -0.0013(4) 0.0042(3) -0.0035(3) C16 0.0149(5) 0.0121(6) 0.0131(5) 0.0019(4) 0.0050(4) 0.0001(4) O16 0.0137(4) 0.0157(5) 0.0135(4) -0.0011(3) 0.0038(3) 0.0000(3) C17 0.0195(5) 0.0153(6) 0.0158(5) 0.0057(4) 0.0032(4) -0.0006(4) O17 0.0137(3) 0.0106(4) 0.0102(3) 0.0009(3) 0.0020(3) -0.0002(3) C18 0.0192(5) 0.0211(7) 0.0151(5) 0.0065(5) 0.0019(4) 0.0012(5) C19 0.0151(5) 0.0184(7) 0.0141(5) 0.0036(4) 0.0010(4) -0.0012(4) C20 0.0131(4) 0.0128(5) 0.0107(4) 0.0007(4) 0.0031(3) -0.0007(4) C21 0.0175(5) 0.0129(6) 0.0145(5) 0.0020(4) 0.0031(4) -0.0029(4) C22 0.0145(5) 0.0129(6) 0.0113(4) -0.0003(4) 0.0020(3) -0.0015(4) C23 0.0159(5) 0.0145(6) 0.0147(5) -0.0015(4) 0.0054(4) 0.0020(4) C24 0.0231(6) 0.0197(8) 0.0410(9) 0.0003(6) 0.0181(6) 0.0048(5) C25 0.0131(4) 0.0112(5) 0.0126(4) 0.0007(4) 0.0029(3) 0.0004(4) C26 0.0234(6) 0.0153(6) 0.0126(5) 0.0028(4) 0.0032(4) 0.0034(4) C27 0.0264(6) 0.0165(7) 0.0152(5) 0.0052(5) 0.0032(4) 0.0056(5) C28 0.0232(6) 0.0124(6) 0.0174(5) 0.0027(4) 0.0039(4) 0.0049(4) C29 0.0165(5) 0.0112(6) 0.0145(5) 0.0008(4) 0.0041(4) 0.0020(4) C30 0.0168(5) 0.0100(5) 0.0120(4) 0.0006(4) 0.0032(4) 0.0012(4) C31 0.0296(7) 0.0133(6) 0.0155(5) -0.0003(4) 0.0054(5) 0.0073(5) C32 0.0193(5) 0.0120(6) 0.0119(5) 0.0010(4) 0.0021(4) -0.0037(4) C33 0.0248(6) 0.0237(8) 0.0211(6) -0.0080(5) 0.0022(5) -0.0061(5) C34 0.0132(4) 0.0107(5) 0.0133(5) -0.0005(4) 0.0019(4) 0.0021(4) C35 0.0131(4) 0.0116(5) 0.0127(4) 0.0004(4) 0.0040(3) 0.0013(4) C36 0.0178(5) 0.0308(8) 0.0152(5) -0.0043(5) 0.0080(4) -0.0039(5) C1S 0.0215(7) 0.0393(11) 0.0309(8) -0.0091(7) 0.0036(6) 0.0009(6) C2S 0.0340(8) 0.0327(10) 0.0268(7) -0.0018(7) 0.0086(6) -0.0008(7) N1S 0.0405(9) 0.0394(11) 0.0563(12) -0.0136(9) 0.0058(8) 0.0043(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 Zn1 O14 1.9586(10) . ? Zn1 O4 1.9782(10) . ? Zn1 O15 2.0539(9) . ? Zn1 O5 2.0669(9) . ? Zn1 N1 2.1863(10) . ? C1 N1 1.3586(16) . ? C1 C2 1.3846(18) . ? C1 C6 1.5014(19) . ? N1 C5 1.3386(17) . ? Zn2 O14 1.9719(9) . ? Zn2 O8 2.0529(10) . ? Zn2 N3 2.0781(10) . ? Zn2 O17 2.1200(9) . ? Zn2 O7 2.2144(10) . ? Zn2 O5 2.2592(9) . ? Zn2 Zn3 3.1456(2) . ? C2 C3 1.391(2) . ? O2 C6 1.4332(16) . ? N2 C13 1.3356(16) . ? N2 C9 1.3403(18) . ? N2 Zn3 2.0664(11) . ? Zn3 O10 1.9573(10) . ? Zn3 O16 2.0783(9) . ? Zn3 O5 2.1141(9) . ? Zn3 O17 2.2445(9) . ? Zn3 O6 2.2572(10) . ? C3 C4 1.3820(19) . ? O3 C7 1.2405(16) . ? N3 C20 1.3381(16) . ? N3 C16 1.3384(17) . ? Zn4 O11 1.9704(10) . ? Zn4 O10 1.9712(9) . ? Zn4 O9 2.0015(10) . ? Zn4 O17 2.0853(9) . ? Zn4 N4 2.2054(11) . ? C4 C5 1.3971(17) . ? O4 C7 1.2742(17) . ? N4 C25 1.3405(16) . ? N4 C29 1.3542(17) . ? C5 C34 1.5126(17) . ? O5 C14 1.4052(16) . ? O6 C15 1.4203(17) . ? C7 C8 1.509(2) . ? O7 C21 1.4277(16) . ? O8 C23 1.2628(17) . ? C9 C10 1.3879(18) . ? C9 C14 1.5153(17) . ? O9 C23 1.2599(17) . ? C10 C11 1.390(2) . ? O10 C30 1.3845(15) . ? C11 C12 1.384(2) . ? O11 C32 1.2701(16) . ? C12 C13 1.3894(19) . ? O12 C32 1.2491(17) . ? C13 C15 1.513(2) . ? O13 C31 1.4170(18) . ? O14 C34 1.3889(15) . ? O15 C35 1.2748(15) . ? C16 C17 1.3919(18) . ? C16 C21 1.5058(18) . ? O16 C35 1.2477(15) . ? C17 C18 1.389(2) . ? O17 C22 1.4027(14) . ? C18 C19 1.389(2) . ? C19 C20 1.3891(17) . ? C20 C22 1.5104(18) . ? C23 C24 1.5073(19) . ? C25 C26 1.3955(18) . ? C25 C30 1.5137(18) . ? C26 C27 1.380(2) . ? C27 C28 1.387(2) . ? C28 C29 1.3888(18) . ? C29 C31 1.5054(18) . ? C32 C33 1.5098(19) . ? C35 C36 1.5103(17) . ? C1S N1S 1.143(3) . ? C1S C2S 1.453(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 O14 Zn1 O4 130.87(4) . . ? O14 Zn1 O15 132.26(5) . . ? O4 Zn1 O15 96.83(4) . . ? O14 Zn1 O5 78.67(4) . . ? O4 Zn1 O5 103.30(4) . . ? O15 Zn1 O5 93.92(4) . . ? O14 Zn1 N1 78.92(4) . . ? O4 Zn1 N1 102.51(4) . . ? O15 Zn1 N1 90.28(4) . . ? O5 Zn1 N1 153.14(4) . . ? N1 C1 C2 121.46(12) . . ? N1 C1 C6 117.40(11) . . ? C2 C1 C6 121.14(11) . . ? C5 N1 C1 118.67(11) . . ? C5 N1 Zn1 111.14(8) . . ? C1 N1 Zn1 130.13(9) . . ? O14 Zn2 O8 93.14(4) . . ? O14 Zn2 N3 162.24(4) . . ? O8 Zn2 N3 100.35(4) . . ? O14 Zn2 O17 111.61(4) . . ? O8 Zn2 O17 98.48(4) . . ? N3 Zn2 O17 77.93(4) . . ? O14 Zn2 O7 93.98(4) . . ? O8 Zn2 O7 90.69(4) . . ? N3 Zn2 O7 74.52(4) . . ? O17 Zn2 O7 152.11(3) . . ? O14 Zn2 O5 73.87(4) . . ? O8 Zn2 O5 166.88(4) . . ? N3 Zn2 O5 92.75(4) . . ? O17 Zn2 O5 84.94(3) . . ? O7 Zn2 O5 92.07(3) . . ? O14 Zn2 Zn3 82.11(3) . . ? O8 Zn2 Zn3 135.67(3) . . ? N3 Zn2 Zn3 95.90(3) . . ? O17 Zn2 Zn3 45.48(2) . . ? O7 Zn2 Zn3 133.51(3) . . ? O5 Zn2 Zn3 42.20(2) . . ? C1 C2 C3 119.69(12) . . ? C13 N2 C9 120.87(11) . . ? C13 N2 Zn3 122.33(9) . . ? C9 N2 Zn3 116.25(8) . . ? O10 Zn3 N2 161.62(4) . . ? O10 Zn3 O16 94.13(4) . . ? N2 Zn3 O16 98.88(4) . . ? O10 Zn3 O5 112.50(4) . . ? N2 Zn3 O5 78.89(4) . . ? O16 Zn3 O5 96.76(4) . . ? O10 Zn3 O17 74.24(4) . . ? N2 Zn3 O17 93.08(4) . . ? O16 Zn3 O17 168.04(4) . . ? O5 Zn3 O17 85.45(3) . . ? O10 Zn3 O6 91.96(4) . . ? N2 Zn3 O6 74.62(4) . . ? O16 Zn3 O6 92.53(4) . . ? O5 Zn3 O6 152.98(4) . . ? O17 Zn3 O6 90.67(3) . . ? O10 Zn3 Zn2 82.79(3) . . ? N2 Zn3 Zn2 96.88(3) . . ? O16 Zn3 Zn2 134.91(3) . . ? O5 Zn3 Zn2 45.87(2) . . ? O17 Zn3 Zn2 42.34(2) . . ? O6 Zn3 Zn2 132.43(3) . . ? C4 C3 C2 118.91(12) . . ? C20 N3 C16 120.93(11) . . ? C20 N3 Zn2 117.17(8) . . ? C16 N3 Zn2 121.81(8) . . ? O11 Zn4 O10 130.20(4) . . ? O11 Zn4 O9 99.84(4) . . ? O10 Zn4 O9 129.84(4) . . ? O11 Zn4 O17 101.42(4) . . ? O10 Zn4 O17 77.70(4) . . ? O9 Zn4 O17 97.93(4) . . ? O11 Zn4 N4 99.24(4) . . ? O10 Zn4 N4 78.27(4) . . ? O9 Zn4 N4 92.22(4) . . ? O17 Zn4 N4 155.01(4) . . ? C3 C4 C5 118.62(13) . . ? C7 O4 Zn1 127.40(9) . . ? C25 N4 C29 118.91(11) . . ? C25 N4 Zn4 111.54(8) . . ? C29 N4 Zn4 129.55(8) . . ? N1 C5 C4 122.65(11) . . ? N1 C5 C34 117.24(10) . . ? C4 C5 C34 120.10(11) . . ? C14 O5 Zn1 120.96(8) . . ? C14 O5 Zn3 112.35(7) . . ? Zn1 O5 Zn3 108.16(4) . . ? C14 O5 Zn2 123.47(7) . . ? Zn1 O5 Zn2 95.38(3) . . ? Zn3 O5 Zn2 91.93(4) . . ? O2 C6 C1 111.88(11) . . ? C15 O6 Zn3 114.93(8) . . ? O3 C7 O4 125.77(13) . . ? O3 C7 C8 117.36(13) . . ? O4 C7 C8 116.86(12) . . ? C21 O7 Zn2 116.42(7) . . ? C23 O8 Zn2 127.02(8) . . ? N2 C9 C10 121.14(12) . . ? N2 C9 C14 115.04(11) . . ? C10 C9 C14 123.79(12) . . ? C23 O9 Zn4 137.80(9) . . ? C9 C10 C11 118.31(14) . . ? C30 O10 Zn3 129.10(8) . . ? C30 O10 Zn4 120.58(8) . . ? Zn3 O10 Zn4 110.20(4) . . ? C12 C11 C10 120.03(13) . . ? C32 O11 Zn4 128.64(9) . . ? C11 C12 C13 118.57(13) . . ? N2 C13 C12 121.07(13) . . ? N2 C13 C15 115.62(11) . . ? C12 C13 C15 123.30(12) . . ? O5 C14 C9 111.61(11) . . ? C34 O14 Zn1 119.50(8) . . ? C34 O14 Zn2 129.97(8) . . ? Zn1 O14 Zn2 109.09(4) . . ? O6 C15 C13 111.51(10) . . ? C35 O15 Zn1 137.45(8) . . ? N3 C16 C17 121.39(12) . . ? N3 C16 C21 116.01(11) . . ? C17 C16 C21 122.60(12) . . ? C35 O16 Zn3 129.37(8) . . ? C18 C17 C16 118.27(13) . . ? C22 O17 Zn4 121.73(8) . . ? C22 O17 Zn2 113.42(7) . . ? Zn4 O17 Zn2 105.82(4) . . ? C22 O17 Zn3 122.55(7) . . ? Zn4 O17 Zn3 96.10(3) . . ? Zn2 O17 Zn3 92.18(3) . . ? C19 C18 C17 119.60(12) . . ? C20 C19 C18 119.12(12) . . ? N3 C20 C19 120.67(12) . . ? N3 C20 C22 115.20(10) . . ? C19 C20 C22 124.13(11) . . ? O7 C21 C16 110.69(10) . . ? O17 C22 C20 112.30(10) . . ? O9 C23 O8 125.76(12) . . ? O9 C23 C24 116.67(13) . . ? O8 C23 C24 117.57(12) . . ? N4 C25 C26 122.41(12) . . ? N4 C25 C30 117.24(11) . . ? C26 C25 C30 120.36(11) . . ? C27 C26 C25 118.58(12) . . ? C26 C27 C28 119.33(12) . . ? C27 C28 C29 119.32(13) . . ? N4 C29 C28 121.45(12) . . ? N4 C29 C31 117.25(11) . . ? C28 C29 C31 121.29(12) . . ? O10 C30 C25 111.60(10) . . ? O13 C31 C29 108.49(11) . . ? O12 C32 O11 126.44(12) . . ? O12 C32 C33 117.67(12) . . ? O11 C32 C33 115.88(13) . . ? O14 C34 C5 111.56(10) . . ? O16 C35 O15 125.36(11) . . ? O16 C35 C36 118.84(11) . . ? O15 C35 C36 115.79(11) . . ? N1S C1S C2S 179.3(2) . . ? 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 C2 C1 N1 C5 0.57(18) . . . . ? C6 C1 N1 C5 -178.35(11) . . . . ? C2 C1 N1 Zn1 -176.43(9) . . . . ? C6 C1 N1 Zn1 4.64(17) . . . . ? O14 Zn1 N1 C5 8.38(8) . . . . ? O4 Zn1 N1 C5 138.14(8) . . . . ? O15 Zn1 N1 C5 -124.80(9) . . . . ? O5 Zn1 N1 C5 -25.53(14) . . . . ? O14 Zn1 N1 C1 -174.43(12) . . . . ? O4 Zn1 N1 C1 -44.67(11) . . . . ? O15 Zn1 N1 C1 52.39(11) . . . . ? O5 Zn1 N1 C1 151.65(10) . . . . ? N1 C1 C2 C3 -0.2(2) . . . . ? C6 C1 C2 C3 178.66(12) . . . . ? C13 N2 Zn3 O10 -38.55(19) . . . . ? C9 N2 Zn3 O10 133.03(13) . . . . ? C13 N2 Zn3 O16 95.99(10) . . . . ? C9 N2 Zn3 O16 -92.43(9) . . . . ? C13 N2 Zn3 O5 -168.81(10) . . . . ? C9 N2 Zn3 O5 2.78(9) . . . . ? C13 N2 Zn3 O17 -84.06(10) . . . . ? C9 N2 Zn3 O17 87.53(9) . . . . ? C13 N2 Zn3 O6 5.79(9) . . . . ? C9 N2 Zn3 O6 177.38(10) . . . . ? C13 N2 Zn3 Zn2 -126.40(9) . . . . ? C9 N2 Zn3 Zn2 45.19(9) . . . . ? O14 Zn2 Zn3 O10 56.66(4) . . . . ? O8 Zn2 Zn3 O10 -29.75(5) . . . . ? N3 Zn2 Zn3 O10 -141.12(4) . . . . ? O17 Zn2 Zn3 O10 -74.47(5) . . . . ? O7 Zn2 Zn3 O10 144.66(4) . . . . ? O5 Zn2 Zn3 O10 131.31(4) . . . . ? O14 Zn2 Zn3 N2 -141.86(4) . . . . ? O8 Zn2 Zn3 N2 131.73(5) . . . . ? N3 Zn2 Zn3 N2 20.37(4) . . . . ? O17 Zn2 Zn3 N2 87.01(5) . . . . ? O7 Zn2 Zn3 N2 -53.86(5) . . . . ? O5 Zn2 Zn3 N2 -67.21(4) . . . . ? O14 Zn2 Zn3 O16 -31.99(5) . . . . ? O8 Zn2 Zn3 O16 -118.40(6) . . . . ? N3 Zn2 Zn3 O16 130.24(5) . . . . ? O17 Zn2 Zn3 O16 -163.12(5) . . . . ? O7 Zn2 Zn3 O16 56.02(5) . . . . ? O5 Zn2 Zn3 O16 42.66(5) . . . . ? O14 Zn2 Zn3 O5 -74.65(4) . . . . ? O8 Zn2 Zn3 O5 -161.06(5) . . . . ? N3 Zn2 Zn3 O5 87.58(4) . . . . ? O17 Zn2 Zn3 O5 154.22(5) . . . . ? O7 Zn2 Zn3 O5 13.36(5) . . . . ? O14 Zn2 Zn3 O17 131.13(5) . . . . ? O8 Zn2 Zn3 O17 44.72(5) . . . . ? N3 Zn2 Zn3 O17 -66.64(5) . . . . ? O7 Zn2 Zn3 O17 -140.87(5) . . . . ? O5 Zn2 Zn3 O17 -154.22(5) . . . . ? O14 Zn2 Zn3 O6 142.72(5) . . . . ? O8 Zn2 Zn3 O6 56.31(5) . . . . ? N3 Zn2 Zn3 O6 -55.06(5) . . . . ? O17 Zn2 Zn3 O6 11.59(5) . . . . ? O7 Zn2 Zn3 O6 -129.28(5) . . . . ? O5 Zn2 Zn3 O6 -142.64(5) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? O14 Zn2 N3 C20 131.27(14) . . . . ? O8 Zn2 N3 C20 -89.87(9) . . . . ? O17 Zn2 N3 C20 6.69(9) . . . . ? O7 Zn2 N3 C20 -177.70(10) . . . . ? O5 Zn2 N3 C20 90.92(9) . . . . ? Zn3 Zn2 N3 C20 48.71(9) . . . . ? O14 Zn2 N3 C16 -45.15(19) . . . . ? O8 Zn2 N3 C16 93.71(10) . . . . ? O17 Zn2 N3 C16 -169.73(10) . . . . ? O7 Zn2 N3 C16 5.89(9) . . . . ? O5 Zn2 N3 C16 -85.49(10) . . . . ? Zn3 Zn2 N3 C16 -127.71(9) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? O14 Zn1 O4 C7 -26.15(13) . . . . ? O15 Zn1 O4 C7 155.95(11) . . . . ? O5 Zn1 O4 C7 60.27(11) . . . . ? N1 Zn1 O4 C7 -112.23(11) . . . . ? O11 Zn4 N4 C25 132.99(8) . . . . ? O10 Zn4 N4 C25 3.64(8) . . . . ? O9 Zn4 N4 C25 -126.66(9) . . . . ? O17 Zn4 N4 C25 -12.47(14) . . . . ? O11 Zn4 N4 C29 -45.98(11) . . . . ? O10 Zn4 N4 C29 -175.34(11) . . . . ? O9 Zn4 N4 C29 54.36(11) . . . . ? O17 Zn4 N4 C29 168.55(9) . . . . ? C1 N1 C5 C4 -0.56(18) . . . . ? Zn1 N1 C5 C4 176.98(10) . . . . ? C1 N1 C5 C34 178.50(11) . . . . ? Zn1 N1 C5 C34 -3.96(13) . . . . ? C3 C4 C5 N1 0.20(19) . . . . ? C3 C4 C5 C34 -178.83(12) . . . . ? O14 Zn1 O5 C14 146.79(9) . . . . ? O4 Zn1 O5 C14 17.12(9) . . . . ? O15 Zn1 O5 C14 -80.85(9) . . . . ? N1 Zn1 O5 C14 -179.26(9) . . . . ? O14 Zn1 O5 Zn3 -81.63(5) . . . . ? O4 Zn1 O5 Zn3 148.69(4) . . . . ? O15 Zn1 O5 Zn3 50.72(5) . . . . ? N1 Zn1 O5 Zn3 -47.68(10) . . . . ? O14 Zn1 O5 Zn2 12.18(4) . . . . ? O4 Zn1 O5 Zn2 -117.50(4) . . . . ? O15 Zn1 O5 Zn2 144.53(4) . . . . ? N1 Zn1 O5 Zn2 46.12(9) . . . . ? O10 Zn3 O5 C14 178.61(8) . . . . ? N2 Zn3 O5 C14 -16.49(8) . . . . ? O16 Zn3 O5 C14 81.28(8) . . . . ? O17 Zn3 O5 C14 -110.53(8) . . . . ? O6 Zn3 O5 C14 -28.02(12) . . . . ? Zn2 Zn3 O5 C14 -127.62(9) . . . . ? O10 Zn3 O5 Zn1 42.53(5) . . . . ? N2 Zn3 O5 Zn1 -152.57(5) . . . . ? O16 Zn3 O5 Zn1 -54.80(4) . . . . ? O17 Zn3 O5 Zn1 113.39(4) . . . . ? O6 Zn3 O5 Zn1 -164.10(6) . . . . ? Zn2 Zn3 O5 Zn1 96.30(4) . . . . ? O10 Zn3 O5 Zn2 -53.77(4) . . . . ? N2 Zn3 O5 Zn2 111.13(4) . . . . ? O16 Zn3 O5 Zn2 -151.10(3) . . . . ? O17 Zn3 O5 Zn2 17.09(3) . . . . ? O6 Zn3 O5 Zn2 99.60(8) . . . . ? O14 Zn2 O5 C14 -145.32(10) . . . . ? O8 Zn2 O5 C14 -153.75(15) . . . . ? N3 Zn2 O5 C14 22.82(9) . . . . ? O17 Zn2 O5 C14 100.44(9) . . . . ? O7 Zn2 O5 C14 -51.77(9) . . . . ? Zn3 Zn2 O5 C14 118.58(10) . . . . ? O14 Zn2 O5 Zn1 -12.35(4) . . . . ? O8 Zn2 O5 Zn1 -20.78(18) . . . . ? N3 Zn2 O5 Zn1 155.79(4) . . . . ? O17 Zn2 O5 Zn1 -126.59(4) . . . . ? O7 Zn2 O5 Zn1 81.20(4) . . . . ? Zn3 Zn2 O5 Zn1 -108.45(4) . . . . ? O14 Zn2 O5 Zn3 96.10(4) . . . . ? O8 Zn2 O5 Zn3 87.67(16) . . . . ? N3 Zn2 O5 Zn3 -95.76(4) . . . . ? O17 Zn2 O5 Zn3 -18.14(3) . . . . ? O7 Zn2 O5 Zn3 -170.35(3) . . . . ? N1 C1 C6 O2 -81.62(14) . . . . ? C2 C1 C6 O2 99.46(14) . . . . ? O10 Zn3 O6 C15 168.17(9) . . . . ? N2 Zn3 O6 C15 0.91(9) . . . . ? O16 Zn3 O6 C15 -97.61(9) . . . . ? O5 Zn3 O6 C15 12.65(13) . . . . ? O17 Zn3 O6 C15 93.92(9) . . . . ? Zn2 Zn3 O6 C15 86.14(9) . . . . ? Zn1 O4 C7 O3 3.69(19) . . . . ? Zn1 O4 C7 C8 -177.89(10) . . . . ? O14 Zn2 O7 C21 159.46(9) . . . . ? O8 Zn2 O7 C21 -107.34(9) . . . . ? N3 Zn2 O7 C21 -6.79(8) . . . . ? O17 Zn2 O7 C21 2.41(13) . . . . ? O5 Zn2 O7 C21 85.50(9) . . . . ? Zn3 Zn2 O7 C21 76.56(9) . . . . ? O14 Zn2 O8 C23 -69.69(11) . . . . ? N3 Zn2 O8 C23 121.91(11) . . . . ? O17 Zn2 O8 C23 42.72(11) . . . . ? O7 Zn2 O8 C23 -163.71(11) . . . . ? O5 Zn2 O8 C23 -61.6(2) . . . . ? Zn3 Zn2 O8 C23 12.24(13) . . . . ? C13 N2 C9 C10 0.58(19) . . . . ? Zn3 N2 C9 C10 -171.13(10) . . . . ? C13 N2 C9 C14 -177.62(11) . . . . ? Zn3 N2 C9 C14 10.67(14) . . . . ? O11 Zn4 O9 C23 -123.01(14) . . . . ? O10 Zn4 O9 C23 60.68(15) . . . . ? O17 Zn4 O9 C23 -19.88(14) . . . . ? N4 Zn4 O9 C23 137.22(14) . . . . ? N2 C9 C10 C11 0.2(2) . . . . ? C14 C9 C10 C11 178.23(13) . . . . ? N2 Zn3 O10 C30 146.82(13) . . . . ? O16 Zn3 O10 C30 11.74(11) . . . . ? O5 Zn3 O10 C30 -87.34(11) . . . . ? O17 Zn3 O10 C30 -165.44(12) . . . . ? O6 Zn3 O10 C30 104.42(11) . . . . ? Zn2 Zn3 O10 C30 -123.04(11) . . . . ? N2 Zn3 O10 Zn4 -37.08(16) . . . . ? O16 Zn3 O10 Zn4 -172.17(5) . . . . ? O5 Zn3 O10 Zn4 88.76(5) . . . . ? O17 Zn3 O10 Zn4 10.66(4) . . . . ? O6 Zn3 O10 Zn4 -79.49(5) . . . . ? Zn2 Zn3 O10 Zn4 53.05(4) . . . . ? O11 Zn4 O10 C30 -100.18(10) . . . . ? O9 Zn4 O10 C30 75.07(11) . . . . ? O17 Zn4 O10 C30 165.17(10) . . . . ? N4 Zn4 O10 C30 -7.94(9) . . . . ? O11 Zn4 O10 Zn3 83.34(7) . . . . ? O9 Zn4 O10 Zn3 -101.41(6) . . . . ? O17 Zn4 O10 Zn3 -11.31(5) . . . . ? N4 Zn4 O10 Zn3 175.59(6) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? O10 Zn4 O11 C32 -33.71(14) . . . . ? O9 Zn4 O11 C32 149.99(11) . . . . ? O17 Zn4 O11 C32 49.75(12) . . . . ? N4 Zn4 O11 C32 -116.11(12) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C9 N2 C13 C12 -1.06(19) . . . . ? Zn3 N2 C13 C12 170.15(10) . . . . ? C9 N2 C13 C15 177.65(11) . . . . ? Zn3 N2 C13 C15 -11.14(15) . . . . ? C11 C12 C13 N2 0.7(2) . . . . ? C11 C12 C13 C15 -177.88(14) . . . . ? Zn1 O5 C14 C9 155.85(8) . . . . ? Zn3 O5 C14 C9 26.08(12) . . . . ? Zn2 O5 C14 C9 -82.31(11) . . . . ? N2 C9 C14 O5 -24.61(15) . . . . ? C10 C9 C14 O5 157.25(12) . . . . ? O4 Zn1 O14 C34 -109.20(10) . . . . ? O15 Zn1 O14 C34 67.97(11) . . . . ? O5 Zn1 O14 C34 152.93(10) . . . . ? N1 Zn1 O14 C34 -12.17(9) . . . . ? O4 Zn1 O14 Zn2 83.12(7) . . . . ? O15 Zn1 O14 Zn2 -99.70(6) . . . . ? O5 Zn1 O14 Zn2 -14.75(5) . . . . ? N1 Zn1 O14 Zn2 -179.85(6) . . . . ? O8 Zn2 O14 C34 25.87(11) . . . . ? N3 Zn2 O14 C34 165.47(12) . . . . ? O17 Zn2 O14 C34 -74.54(11) . . . . ? O7 Zn2 O14 C34 116.78(11) . . . . ? O5 Zn2 O14 C34 -152.22(12) . . . . ? Zn3 Zn2 O14 C34 -109.82(11) . . . . ? O8 Zn2 O14 Zn1 -168.16(5) . . . . ? N3 Zn2 O14 Zn1 -28.56(17) . . . . ? O17 Zn2 O14 Zn1 91.44(5) . . . . ? O7 Zn2 O14 Zn1 -77.25(5) . . . . ? O5 Zn2 O14 Zn1 13.75(4) . . . . ? Zn3 Zn2 O14 Zn1 56.15(4) . . . . ? Zn3 O6 C15 C13 -6.19(13) . . . . ? N2 C13 C15 O6 10.82(16) . . . . ? C12 C13 C15 O6 -170.50(12) . . . . ? O14 Zn1 O15 C35 52.65(16) . . . . ? O4 Zn1 O15 C35 -129.50(14) . . . . ? O5 Zn1 O15 C35 -25.58(14) . . . . ? N1 Zn1 O15 C35 127.87(14) . . . . ? C20 N3 C16 C17 -0.26(19) . . . . ? Zn2 N3 C16 C17 176.03(10) . . . . ? C20 N3 C16 C21 179.62(11) . . . . ? Zn2 N3 C16 C21 -4.10(15) . . . . ? O10 Zn3 O16 C35 -81.71(12) . . . . ? N2 Zn3 O16 C35 111.31(11) . . . . ? O5 Zn3 O16 C35 31.55(12) . . . . ? O17 Zn3 O16 C35 -68.5(2) . . . . ? O6 Zn3 O16 C35 -173.87(11) . . . . ? Zn2 Zn3 O16 C35 2.22(13) . . . . ? N3 C16 C17 C18 1.4(2) . . . . ? C21 C16 C17 C18 -178.52(13) . . . . ? O11 Zn4 O17 C22 14.84(9) . . . . ? O10 Zn4 O17 C22 143.89(9) . . . . ? O9 Zn4 O17 C22 -86.94(9) . . . . ? N4 Zn4 O17 C22 160.04(9) . . . . ? O11 Zn4 O17 Zn2 146.22(4) . . . . ? O10 Zn4 O17 Zn2 -84.74(4) . . . . ? O9 Zn4 O17 Zn2 44.43(5) . . . . ? N4 Zn4 O17 Zn2 -68.59(9) . . . . ? O11 Zn4 O17 Zn3 -119.76(4) . . . . ? O10 Zn4 O17 Zn3 9.29(4) . . . . ? O9 Zn4 O17 Zn3 138.46(4) . . . . ? N4 Zn4 O17 Zn3 25.43(10) . . . . ? O14 Zn2 O17 C22 179.53(8) . . . . ? O8 Zn2 O17 C22 82.71(8) . . . . ? N3 Zn2 O17 C22 -16.14(8) . . . . ? O7 Zn2 O17 C22 -25.20(13) . . . . ? O5 Zn2 O17 C22 -110.05(8) . . . . ? Zn3 Zn2 O17 C22 -127.10(9) . . . . ? O14 Zn2 O17 Zn4 43.60(5) . . . . ? O8 Zn2 O17 Zn4 -53.21(4) . . . . ? N3 Zn2 O17 Zn4 -152.07(5) . . . . ? O7 Zn2 O17 Zn4 -161.13(6) . . . . ? O5 Zn2 O17 Zn4 114.03(4) . . . . ? Zn3 Zn2 O17 Zn4 96.97(4) . . . . ? O14 Zn2 O17 Zn3 -53.37(4) . . . . ? O8 Zn2 O17 Zn3 -150.19(4) . . . . ? N3 Zn2 O17 Zn3 110.96(4) . . . . ? O7 Zn2 O17 Zn3 101.90(7) . . . . ? O5 Zn2 O17 Zn3 17.05(3) . . . . ? O10 Zn3 O17 C22 -143.58(10) . . . . ? N2 Zn3 O17 C22 22.91(9) . . . . ? O16 Zn3 O17 C22 -157.31(16) . . . . ? O5 Zn3 O17 C22 101.50(9) . . . . ? O6 Zn3 O17 C22 -51.73(9) . . . . ? Zn2 Zn3 O17 C22 119.75(10) . . . . ? O10 Zn3 O17 Zn4 -9.50(4) . . . . ? N2 Zn3 O17 Zn4 156.99(4) . . . . ? O16 Zn3 O17 Zn4 -23.23(19) . . . . ? O5 Zn3 O17 Zn4 -124.42(4) . . . . ? O6 Zn3 O17 Zn4 82.36(4) . . . . ? Zn2 Zn3 O17 Zn4 -106.17(4) . . . . ? O10 Zn3 O17 Zn2 96.67(4) . . . . ? N2 Zn3 O17 Zn2 -96.84(4) . . . . ? O16 Zn3 O17 Zn2 82.94(18) . . . . ? O5 Zn3 O17 Zn2 -18.25(3) . . . . ? O6 Zn3 O17 Zn2 -171.47(4) . . . . ? C16 C17 C18 C19 -0.9(2) . . . . ? C17 C18 C19 C20 -0.5(2) . . . . ? C16 N3 C20 C19 -1.25(19) . . . . ? Zn2 N3 C20 C19 -177.70(10) . . . . ? C16 N3 C20 C22 179.82(11) . . . . ? Zn2 N3 C20 C22 3.37(14) . . . . ? C18 C19 C20 N3 1.6(2) . . . . ? C18 C19 C20 C22 -179.57(13) . . . . ? Zn2 O7 C21 C16 6.74(13) . . . . ? N3 C16 C21 O7 -2.07(16) . . . . ? C17 C16 C21 O7 177.81(12) . . . . ? Zn4 O17 C22 C20 150.35(8) . . . . ? Zn2 O17 C22 C20 22.24(12) . . . . ? Zn3 O17 C22 C20 -86.76(11) . . . . ? N3 C20 C22 O17 -17.12(15) . . . . ? C19 C20 C22 O17 163.99(12) . . . . ? Zn4 O9 C23 O8 0.7(2) . . . . ? Zn4 O9 C23 C24 -179.68(11) . . . . ? Zn2 O8 C23 O9 -14.61(19) . . . . ? Zn2 O8 C23 C24 165.77(10) . . . . ? C29 N4 C25 C26 0.12(18) . . . . ? Zn4 N4 C25 C26 -178.97(10) . . . . ? C29 N4 C25 C30 179.67(11) . . . . ? Zn4 N4 C25 C30 0.57(13) . . . . ? N4 C25 C26 C27 0.2(2) . . . . ? C30 C25 C26 C27 -179.36(12) . . . . ? C25 C26 C27 C28 -0.1(2) . . . . ? C26 C27 C28 C29 -0.3(2) . . . . ? C25 N4 C29 C28 -0.53(18) . . . . ? Zn4 N4 C29 C28 178.39(10) . . . . ? C25 N4 C29 C31 -179.68(12) . . . . ? Zn4 N4 C29 C31 -0.77(17) . . . . ? C27 C28 C29 N4 0.6(2) . . . . ? C27 C28 C29 C31 179.75(13) . . . . ? Zn3 O10 C30 C25 -173.97(8) . . . . ? Zn4 O10 C30 C25 10.29(14) . . . . ? N4 C25 C30 O10 -6.51(16) . . . . ? C26 C25 C30 O10 173.04(11) . . . . ? N4 C29 C31 O13 -179.69(12) . . . . ? C28 C29 C31 O13 1.15(19) . . . . ? Zn4 O11 C32 O12 4.3(2) . . . . ? Zn4 O11 C32 C33 -175.94(10) . . . . ? Zn1 O14 C34 C5 13.33(14) . . . . ? Zn2 O14 C34 C5 178.07(8) . . . . ? N1 C5 C34 O14 -5.14(16) . . . . ? C4 C5 C34 O14 173.94(11) . . . . ? Zn3 O16 C35 O15 -1.2(2) . . . . ? Zn3 O16 C35 C36 177.98(10) . . . . ? Zn1 O15 C35 O16 -3.0(2) . . . . ? Zn1 O15 C35 C36 177.84(11) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 39.93 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.075 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.112 # Attachment 'AWK397_0m.cif' data_awk397_0m _database_code_depnum_ccdc_archive 'CCDC 717123' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N O6 Zn' _chemical_formula_weight 320.59 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.9474(4) _cell_length_b 7.1604(4) _cell_length_c 9.0734(5) _cell_angle_alpha 100.9590(10) _cell_angle_beta 107.7710(10) _cell_angle_gamma 107.1430(10) _cell_volume 334.54(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6866 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description Block _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 164 _exptl_absorpt_coefficient_mu 1.856 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7401 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 6897 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.84 _diffrn_reflns_theta_max 36.49 _reflns_number_total 4279 _reflns_number_gt 4270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2008.6-1' _computing_cell_refinement 'Bruker APEX2 v2008.6-1' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-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^)+(0.0422P)^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 noref _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 0.036(7) _refine_ls_number_reflns 4279 _refine_ls_number_parameters 174 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _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 Zn1 Zn 0.5631 0.2179 0.4218 0.00854(4) Uani 1 1 d . . . O1 O 0.1934(3) 0.1728(2) 0.73892(16) 0.0154(2) Uani 1 1 d . . . N1 N 0.4347(3) -0.0215(2) 0.21676(16) 0.0104(2) Uani 1 1 d . . . C1 C 0.6406(4) 0.2651(4) 0.8138(2) 0.0255(4) Uani 1 1 d . . . H1A H 0.6348 0.2594 0.9197 0.038 Uiso 1 1 calc R . . H1B H 0.7456 0.4048 0.8240 0.038 Uiso 1 1 calc R . . H1C H 0.7146 0.1691 0.7769 0.038 Uiso 1 1 calc R . . O2 O 0.3404(3) 0.1924(2) 0.54406(15) 0.0133(2) Uani 1 1 d . . . C2 C 0.3742(3) 0.2069(2) 0.69203(18) 0.0113(2) Uani 1 1 d . . . O3 O 0.8575(3) 0.48030(19) 0.53793(16) 0.0134(2) Uani 1 1 d . . . C3 C 1.2631(4) 0.6696(3) 0.5389(3) 0.0187(3) Uani 1 1 d . . . H3A H 1.3975 0.6140 0.5637 0.028 Uiso 1 1 calc R . . H3B H 1.2746 0.7583 0.6398 0.028 Uiso 1 1 calc R . . H3C H 1.2842 0.7498 0.4644 0.028 Uiso 1 1 calc R . . O4 O 0.9441(3) 0.3719(2) 0.32392(17) 0.0168(2) Uani 1 1 d . . . C4 C 1.0060(3) 0.4954(2) 0.4604(2) 0.0114(2) Uani 1 1 d . . . O5 O 0.2953(3) 0.2944(2) 0.24251(15) 0.0126(2) Uani 1 1 d . . . C5 C 0.1511(4) 0.1366(3) 0.09096(19) 0.0149(3) Uani 1 1 d . . . H5A H 0.1568 0.1955 0.0013 0.018 Uiso 1 1 calc R . . H5B H -0.0290 0.0786 0.0786 0.018 Uiso 1 1 calc R . . O6 O 0.7517(3) 0.0214(2) 0.50309(16) 0.0129(2) Uani 1 1 d . . . C6 C 0.2543(3) -0.0320(3) 0.07990(18) 0.0120(3) Uani 1 1 d . . . C7 C 0.1697(4) -0.1905(3) -0.0633(2) 0.0173(3) Uani 1 1 d . . . H7 H 0.0433 -0.1963 -0.1601 0.021 Uiso 1 1 calc R . . C8 C 0.2744(4) -0.3406(3) -0.0618(2) 0.0190(3) Uani 1 1 d . . . H8 H 0.2183 -0.4516 -0.1576 0.023 Uiso 1 1 calc R . . C9 C 0.4620(4) -0.3272(3) 0.0810(2) 0.0170(3) Uani 1 1 d . . . H9 H 0.5351 -0.4285 0.0842 0.020 Uiso 1 1 calc R . . C10 C 0.5399(3) -0.1628(2) 0.2186(2) 0.0118(2) Uani 1 1 d . . . C11 C 0.7484(4) -0.1314(3) 0.3766(2) 0.0146(3) Uani 1 1 d . . . H11A H 0.7189 -0.2621 0.4033 0.017 Uiso 1 1 calc R . . H11B H 0.9152 -0.0886 0.3657 0.017 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 0.00842(7) 0.00926(6) 0.00825(6) 0.00158(4) 0.00441(4) 0.00321(4) O1 0.0127(5) 0.0252(6) 0.0114(4) 0.0062(4) 0.0075(4) 0.0080(5) N1 0.0102(5) 0.0106(5) 0.0098(4) 0.0015(4) 0.0043(4) 0.0038(4) C1 0.0117(7) 0.0452(12) 0.0135(6) 0.0032(7) 0.0020(6) 0.0091(8) O2 0.0114(5) 0.0212(5) 0.0109(4) 0.0070(4) 0.0071(4) 0.0071(4) C2 0.0106(6) 0.0133(6) 0.0104(5) 0.0034(4) 0.0043(4) 0.0050(5) O3 0.0124(5) 0.0114(5) 0.0155(5) 0.0020(4) 0.0078(4) 0.0021(4) C3 0.0141(7) 0.0138(6) 0.0251(8) 0.0025(5) 0.0099(6) 0.0009(5) O4 0.0140(5) 0.0207(6) 0.0147(5) 0.0004(4) 0.0074(4) 0.0066(4) C4 0.0098(6) 0.0111(5) 0.0152(6) 0.0043(4) 0.0067(5) 0.0044(4) O5 0.0148(5) 0.0149(5) 0.0098(4) 0.0027(4) 0.0054(4) 0.0078(4) C5 0.0165(7) 0.0209(7) 0.0095(5) 0.0036(5) 0.0045(5) 0.0113(6) O6 0.0114(5) 0.0144(5) 0.0130(4) 0.0034(4) 0.0040(4) 0.0062(4) C6 0.0117(6) 0.0140(6) 0.0096(5) 0.0021(4) 0.0041(5) 0.0046(5) C7 0.0197(8) 0.0166(7) 0.0103(5) -0.0012(5) 0.0037(5) 0.0052(6) C8 0.0221(8) 0.0146(6) 0.0154(6) -0.0018(5) 0.0063(6) 0.0053(6) C9 0.0209(8) 0.0112(6) 0.0181(6) 0.0007(5) 0.0084(6) 0.0065(5) C10 0.0129(6) 0.0089(5) 0.0140(5) 0.0020(4) 0.0063(5) 0.0043(4) C11 0.0135(6) 0.0148(6) 0.0164(6) 0.0034(5) 0.0052(5) 0.0082(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 Zn1 O2 1.9622(14) . ? Zn1 O3 1.9717(12) . ? Zn1 N1 2.0326(14) . ? Zn1 O6 2.1451(13) . ? Zn1 O5 2.1804(12) . ? O1 C2 1.249(2) . ? N1 C10 1.337(2) . ? N1 C6 1.343(2) . ? C1 C2 1.507(3) . ? O2 C2 1.274(2) . ? O3 C4 1.280(2) . ? C3 C4 1.508(2) . ? O4 C4 1.251(2) . ? O5 C5 1.422(2) . ? C5 C6 1.508(3) . ? O6 C11 1.418(2) . ? C6 C7 1.391(2) . ? C7 C8 1.393(3) . ? C8 C9 1.393(3) . ? C9 C10 1.388(3) . ? C10 C11 1.507(2) . ? 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 O3 107.94(6) . . ? O2 Zn1 N1 114.38(6) . . ? O3 Zn1 N1 137.68(6) . . ? O2 Zn1 O6 99.02(6) . . ? O3 Zn1 O6 97.25(5) . . ? N1 Zn1 O6 76.95(5) . . ? O2 Zn1 O5 89.42(5) . . ? O3 Zn1 O5 103.74(5) . . ? N1 Zn1 O5 76.93(5) . . ? O6 Zn1 O5 153.75(5) . . ? C10 N1 C6 120.76(15) . . ? C10 N1 Zn1 119.06(11) . . ? C6 N1 Zn1 120.12(12) . . ? C2 O2 Zn1 134.56(12) . . ? O1 C2 O2 122.06(15) . . ? O1 C2 C1 119.07(16) . . ? O2 C2 C1 118.86(17) . . ? C4 O3 Zn1 108.10(11) . . ? O4 C4 O3 122.26(15) . . ? O4 C4 C3 120.00(17) . . ? O3 C4 C3 117.74(16) . . ? C5 O5 Zn1 114.63(10) . . ? O5 C5 C6 111.03(13) . . ? C11 O6 Zn1 114.64(10) . . ? N1 C6 C7 121.17(17) . . ? N1 C6 C5 116.34(14) . . ? C7 C6 C5 122.50(15) . . ? C6 C7 C8 118.49(16) . . ? C9 C8 C7 119.65(17) . . ? C10 C9 C8 118.64(18) . . ? N1 C10 C9 121.28(15) . . ? N1 C10 C11 116.40(14) . . ? C9 C10 C11 122.31(16) . . ? O6 C11 C10 109.80(14) . . ? 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 O2 Zn1 N1 C10 -102.51(13) . . . . ? O3 Zn1 N1 C10 78.03(15) . . . . ? O6 Zn1 N1 C10 -8.41(13) . . . . ? O5 Zn1 N1 C10 174.18(14) . . . . ? O2 Zn1 N1 C6 80.29(14) . . . . ? O3 Zn1 N1 C6 -99.17(15) . . . . ? O6 Zn1 N1 C6 174.39(14) . . . . ? O5 Zn1 N1 C6 -3.01(13) . . . . ? O3 Zn1 O2 C2 -51.62(18) . . . . ? N1 Zn1 O2 C2 128.77(17) . . . . ? O6 Zn1 O2 C2 49.09(17) . . . . ? O5 Zn1 O2 C2 -155.88(17) . . . . ? Zn1 O2 C2 O1 -176.21(14) . . . . ? Zn1 O2 C2 C1 3.2(3) . . . . ? O2 Zn1 O3 C4 178.63(11) . . . . ? N1 Zn1 O3 C4 -1.89(15) . . . . ? O6 Zn1 O3 C4 76.67(11) . . . . ? O5 Zn1 O3 C4 -87.46(12) . . . . ? Zn1 O3 C4 O4 8.6(2) . . . . ? Zn1 O3 C4 C3 -171.52(13) . . . . ? O2 Zn1 O5 C5 -107.39(13) . . . . ? O3 Zn1 O5 C5 144.27(13) . . . . ? N1 Zn1 O5 C5 7.84(12) . . . . ? O6 Zn1 O5 C5 2.1(2) . . . . ? Zn1 O5 C5 C6 -10.78(19) . . . . ? O2 Zn1 O6 C11 128.64(12) . . . . ? O3 Zn1 O6 C11 -121.81(12) . . . . ? N1 Zn1 O6 C11 15.55(12) . . . . ? O5 Zn1 O6 C11 21.26(19) . . . . ? C10 N1 C6 C7 0.6(3) . . . . ? Zn1 N1 C6 C7 177.78(14) . . . . ? C10 N1 C6 C5 -179.23(16) . . . . ? Zn1 N1 C6 C5 -2.1(2) . . . . ? O5 C5 C6 N1 8.6(2) . . . . ? O5 C5 C6 C7 -171.25(17) . . . . ? N1 C6 C7 C8 0.7(3) . . . . ? C5 C6 C7 C8 -179.47(19) . . . . ? C6 C7 C8 C9 -0.9(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C6 N1 C10 C9 -1.7(3) . . . . ? Zn1 N1 C10 C9 -178.91(14) . . . . ? C6 N1 C10 C11 177.47(16) . . . . ? Zn1 N1 C10 C11 0.3(2) . . . . ? C8 C9 C10 N1 1.5(3) . . . . ? C8 C9 C10 C11 -177.67(18) . . . . ? Zn1 O6 C11 C10 -19.18(17) . . . . ? N1 C10 C11 O6 12.7(2) . . . . ? C9 C10 C11 O6 -168.10(17) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 36.49 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 1.670 _refine_diff_density_min -1.620 _refine_diff_density_rms 0.094 # Attachment 'AWK390_0m.cif' data_awk390_0m _database_code_depnum_ccdc_archive 'CCDC 717124' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N2 O8 Zn2' _chemical_formula_weight 525.12 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5747(5) _cell_length_b 9.3319(6) _cell_length_c 13.8853(7) _cell_angle_alpha 97.906(3) _cell_angle_beta 91.158(3) _cell_angle_gamma 111.763(2) _cell_volume 1019.01(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5275 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 38.17 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 2.402 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6266 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS Version 2.1 2003 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_support 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22089 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 38.33 _reflns_number_total 10084 _reflns_number_gt 8704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex v1.0-22 2002' _computing_cell_refinement 'Bruker-Nonius Apex v1.0-22 2002' _computing_data_reduction 'SAINT+ Version 7.06A Bruker-Nonius, 2004' _computing_structure_solution 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_publication_material 'Shelxtl Version 6.12 (Sheldrick, 2001)' _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^)+(0.0457P)^2^+0.2221P] 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 10084 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.131800(16) 0.739379(16) 0.269000(9) 0.01198(4) Uani 1 1 d . . . O1 O 0.05403(11) 0.48657(11) 0.23157(6) 0.01515(14) Uani 1 1 d . . . N1 N -0.03229(12) 0.65060(12) 0.37683(7) 0.01287(15) Uani 1 1 d . . . C1 C -0.11242(13) 0.49634(14) 0.36937(8) 0.01254(16) Uani 1 1 d . . . Zn2 Zn 0.363685(16) 1.071227(17) 0.253794(10) 0.01373(4) Uani 1 1 d . . . O2 O 0.14334(10) 0.96981(11) 0.29973(6) 0.01440(14) Uani 1 1 d . . . C2 C -0.21693(15) 0.42713(15) 0.43935(9) 0.01605(19) Uani 1 1 d . . . H2 H -0.2733 0.3169 0.4321 0.019 Uiso 1 1 calc R . . N2 N -0.04247(12) 0.74095(13) 0.15801(7) 0.01400(15) Uani 1 1 d . . . C3 C -0.23662(16) 0.52316(17) 0.51992(9) 0.0180(2) Uani 1 1 d . . . H3 H -0.3065 0.4794 0.5690 0.022 Uiso 1 1 calc R . . O3 O 0.28829(12) 0.73600(12) 0.15233(7) 0.01757(16) Uani 1 1 d . . . O4 O 0.35047(13) 0.97630(12) 0.11594(7) 0.01937(17) Uani 1 1 d . . . C4 C -0.15299(16) 0.68405(17) 0.52803(8) 0.0174(2) Uani 1 1 d . . . H4 H -0.1649 0.7518 0.5825 0.021 Uiso 1 1 calc R . . C5 C -0.05206(15) 0.74342(15) 0.45518(8) 0.01509(18) Uani 1 1 d . . . H5 H 0.0053 0.8533 0.4605 0.018 Uiso 1 1 calc R . . O5 O 0.33790(11) 0.78773(12) 0.36513(7) 0.01730(15) Uani 1 1 d . . . C6 C -0.08671(14) 0.39871(15) 0.27957(9) 0.01514(18) Uani 1 1 d . . . H6A H -0.0688 0.3072 0.2985 0.018 Uiso 1 1 calc R . . H6B H -0.1892 0.3598 0.2341 0.018 Uiso 1 1 calc R . . O6 O 0.51970(12) 1.01928(12) 0.33529(7) 0.01922(17) Uani 1 1 d . . . C7 C -0.07254(14) 0.87216(15) 0.16485(9) 0.01539(18) Uani 1 1 d . . . O7 O 0.49407(11) 1.29029(12) 0.25002(8) 0.02018(17) Uani 1 1 d . . . O8 O 0.26188(11) 1.34158(12) 0.24228(7) 0.01874(16) Uani 1 1 d . . . C8 C -0.16458(18) 0.90047(19) 0.09058(11) 0.0237(2) Uani 1 1 d . . . H8 H -0.1865 0.9938 0.0972 0.028 Uiso 1 1 calc R . . C9 C -0.2233(2) 0.7901(2) 0.00708(11) 0.0267(3) Uani 1 1 d . . . H9 H -0.2856 0.8072 -0.0445 0.032 Uiso 1 1 calc R . . C10 C -0.19037(18) 0.65429(19) -0.00037(10) 0.0222(2) Uani 1 1 d . . . H10 H -0.2289 0.5772 -0.0570 0.027 Uiso 1 1 calc R . . C11 C -0.09968(16) 0.63406(16) 0.07708(9) 0.01734(19) Uani 1 1 d . . . H11 H -0.0772 0.5411 0.0727 0.021 Uiso 1 1 calc R . . C12 C 0.00288(15) 0.98862(16) 0.25694(10) 0.0175(2) Uani 1 1 d . . . H12A H 0.0377 1.0959 0.2412 0.021 Uiso 1 1 calc R . . H12B H -0.0840 0.9756 0.3045 0.021 Uiso 1 1 calc R . . C13 C 0.32545(14) 0.83225(15) 0.09368(9) 0.01579(18) Uani 1 1 d . . . C14 C 0.3366(2) 0.77563(18) -0.01204(10) 0.0249(3) Uani 1 1 d . . . H14A H 0.3720 0.6865 -0.0169 0.037 Uiso 1 1 calc R . . H14B H 0.4191 0.8601 -0.0404 0.037 Uiso 1 1 calc R . . H14C H 0.2261 0.7435 -0.0475 0.037 Uiso 1 1 calc R . . C15 C 0.47928(14) 0.89736(15) 0.37499(9) 0.01558(18) Uani 1 1 d . . . C16 C 0.61538(16) 0.88279(19) 0.43905(10) 0.0218(2) Uani 1 1 d . . . H16A H 0.5636 0.8159 0.4875 0.033 Uiso 1 1 calc R . . H16B H 0.6885 0.9865 0.4725 0.033 Uiso 1 1 calc R . . H16C H 0.6824 0.8365 0.3988 0.033 Uiso 1 1 calc R . . C17 C 0.41790(14) 1.38295(14) 0.24207(8) 0.01318(17) Uani 1 1 d . . . C18 C 0.52681(17) 1.54651(17) 0.23018(12) 0.0238(3) Uani 1 1 d . . . H18A H 0.5700 1.5463 0.1654 0.036 Uiso 1 1 calc R . . H18B H 0.6214 1.5877 0.2802 0.036 Uiso 1 1 calc R . . H18C H 0.4602 1.6125 0.2372 0.036 Uiso 1 1 calc R . . H1O H 0.133(3) 0.448(4) 0.2378(18) 0.039(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01158(6) 0.01140(6) 0.01345(6) 0.00284(5) 0.00145(4) 0.00454(4) O1 0.0152(3) 0.0143(4) 0.0183(3) 0.0047(3) 0.0061(3) 0.0072(3) N1 0.0123(3) 0.0130(4) 0.0135(3) 0.0019(3) 0.0007(3) 0.0051(3) C1 0.0110(4) 0.0130(4) 0.0142(4) 0.0029(3) 0.0008(3) 0.0050(3) Zn2 0.01239(6) 0.01122(6) 0.01747(6) 0.00230(5) 0.00167(4) 0.00430(5) O2 0.0125(3) 0.0130(4) 0.0176(3) 0.0017(3) 0.0008(3) 0.0050(3) C2 0.0154(4) 0.0166(5) 0.0164(4) 0.0046(4) 0.0032(4) 0.0055(4) N2 0.0137(4) 0.0132(4) 0.0156(4) 0.0026(3) 0.0008(3) 0.0055(3) C3 0.0187(5) 0.0210(6) 0.0155(4) 0.0055(4) 0.0044(4) 0.0079(4) O3 0.0185(4) 0.0177(4) 0.0199(4) 0.0071(3) 0.0067(3) 0.0090(3) O4 0.0246(4) 0.0147(4) 0.0187(4) 0.0040(3) 0.0057(3) 0.0066(3) C4 0.0195(5) 0.0215(6) 0.0133(4) 0.0023(4) 0.0022(4) 0.0102(4) C5 0.0164(4) 0.0147(5) 0.0147(4) 0.0006(4) 0.0003(3) 0.0072(4) O5 0.0143(3) 0.0176(4) 0.0192(4) 0.0047(3) -0.0012(3) 0.0046(3) C6 0.0139(4) 0.0127(4) 0.0180(4) 0.0014(4) 0.0034(4) 0.0042(3) O6 0.0157(4) 0.0171(4) 0.0249(4) 0.0059(4) -0.0009(3) 0.0054(3) C7 0.0126(4) 0.0152(5) 0.0190(4) 0.0040(4) 0.0009(3) 0.0056(4) O7 0.0143(4) 0.0119(4) 0.0356(5) 0.0035(4) 0.0009(3) 0.0064(3) O8 0.0140(3) 0.0178(4) 0.0265(4) 0.0056(4) 0.0038(3) 0.0074(3) C8 0.0245(6) 0.0224(6) 0.0281(6) 0.0072(5) -0.0032(5) 0.0123(5) C9 0.0287(7) 0.0294(8) 0.0237(6) 0.0084(6) -0.0055(5) 0.0120(6) C10 0.0237(6) 0.0252(7) 0.0167(5) 0.0028(5) -0.0023(4) 0.0085(5) C11 0.0184(5) 0.0174(5) 0.0161(4) 0.0016(4) 0.0001(4) 0.0070(4) C12 0.0144(4) 0.0145(5) 0.0242(5) -0.0006(4) 0.0004(4) 0.0074(4) C13 0.0143(4) 0.0152(5) 0.0172(4) 0.0031(4) 0.0040(4) 0.0044(4) C14 0.0322(7) 0.0184(6) 0.0194(5) 0.0013(5) 0.0099(5) 0.0044(5) C15 0.0141(4) 0.0165(5) 0.0169(4) 0.0017(4) -0.0003(3) 0.0069(4) C16 0.0164(5) 0.0268(7) 0.0229(5) 0.0051(5) -0.0031(4) 0.0088(5) C17 0.0147(4) 0.0104(4) 0.0145(4) 0.0007(3) 0.0007(3) 0.0053(3) C18 0.0178(5) 0.0134(5) 0.0410(7) 0.0065(5) 0.0044(5) 0.0059(4) _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 O5 2.0631(9) . ? Zn1 O2 2.0985(9) . ? Zn1 N1 2.1142(9) . ? Zn1 O3 2.1286(9) . ? Zn1 N2 2.1302(10) . ? Zn1 O1 2.1823(10) . ? Zn1 Zn2 3.0363(3) . ? O1 C6 1.4220(14) . ? N1 C1 1.3333(16) . ? N1 C5 1.3490(15) . ? C1 C2 1.3940(15) . ? C1 C6 1.5102(16) . ? Zn2 O2 1.9393(8) . ? Zn2 O7 1.9414(10) . ? Zn2 O6 1.9687(9) . ? Zn2 O4 1.9778(10) . ? O2 C12 1.4110(15) . ? C2 C3 1.3883(18) . ? N2 C7 1.3334(16) . ? N2 C11 1.3434(17) . ? C3 C4 1.390(2) . ? O3 C13 1.2535(15) . ? O4 C13 1.2719(16) . ? C4 C5 1.3832(16) . ? O5 C15 1.2530(16) . ? O6 C15 1.2674(16) . ? C7 C8 1.3974(18) . ? C7 C12 1.5157(18) . ? O7 C17 1.2761(14) . ? O8 C17 1.2475(14) . ? C8 C9 1.386(2) . ? C9 C10 1.388(2) . ? C10 C11 1.3885(18) . ? C13 C14 1.5077(18) . ? C15 C16 1.5102(17) . ? C17 C18 1.4992(19) . ? 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 O5 Zn1 O2 91.99(4) . . ? O5 Zn1 N1 90.52(4) . . ? O2 Zn1 N1 96.67(4) . . ? O5 Zn1 O3 88.45(4) . . ? O2 Zn1 O3 105.88(4) . . ? N1 Zn1 O3 157.45(4) . . ? O5 Zn1 N2 165.92(4) . . ? O2 Zn1 N2 78.54(4) . . ? N1 Zn1 N2 100.82(4) . . ? O3 Zn1 N2 84.23(4) . . ? O5 Zn1 O1 99.94(4) . . ? O2 Zn1 O1 165.99(3) . . ? N1 Zn1 O1 76.06(4) . . ? O3 Zn1 O1 81.93(4) . . ? N2 Zn1 O1 90.94(4) . . ? O5 Zn1 Zn2 74.58(3) . . ? O2 Zn1 Zn2 39.30(2) . . ? N1 Zn1 Zn2 130.64(3) . . ? O3 Zn1 Zn2 70.52(3) . . ? N2 Zn1 Zn2 91.62(3) . . ? O1 Zn1 Zn2 151.92(2) . . ? C6 O1 Zn1 114.53(7) . . ? C1 N1 C5 118.95(10) . . ? C1 N1 Zn1 118.49(7) . . ? C5 N1 Zn1 122.47(8) . . ? N1 C1 C2 122.43(11) . . ? N1 C1 C6 116.49(9) . . ? C2 C1 C6 121.07(11) . . ? O2 Zn2 O7 130.77(4) . . ? O2 Zn2 O6 105.21(4) . . ? O7 Zn2 O6 100.76(4) . . ? O2 Zn2 O4 106.22(4) . . ? O7 Zn2 O4 102.17(4) . . ? O6 Zn2 O4 111.14(4) . . ? O2 Zn2 Zn1 43.26(3) . . ? O7 Zn2 Zn1 174.03(3) . . ? O6 Zn2 Zn1 82.36(3) . . ? O4 Zn2 Zn1 81.23(3) . . ? C12 O2 Zn2 119.10(8) . . ? C12 O2 Zn1 112.55(8) . . ? Zn2 O2 Zn1 97.44(4) . . ? C3 C2 C1 118.39(12) . . ? C7 N2 C11 119.31(10) . . ? C7 N2 Zn1 114.79(8) . . ? C11 N2 Zn1 125.01(8) . . ? C2 C3 C4 119.33(11) . . ? C13 O3 Zn1 124.33(8) . . ? C13 O4 Zn2 120.57(8) . . ? C5 C4 C3 118.67(11) . . ? N1 C5 C4 122.23(12) . . ? C15 O5 Zn1 130.52(8) . . ? O1 C6 C1 111.33(10) . . ? C15 O6 Zn2 124.70(8) . . ? N2 C7 C8 121.69(12) . . ? N2 C7 C12 115.55(10) . . ? C8 C7 C12 122.75(12) . . ? C17 O7 Zn2 119.47(8) . . ? C9 C8 C7 118.89(13) . . ? C8 C9 C10 119.34(12) . . ? C9 C10 C11 118.28(14) . . ? N2 C11 C10 122.48(12) . . ? O2 C12 C7 112.19(10) . . ? O3 C13 O4 124.70(11) . . ? O3 C13 C14 118.97(12) . . ? O4 C13 C14 116.30(11) . . ? O5 C15 O6 126.05(11) . . ? O5 C15 C16 117.31(11) . . ? O6 C15 C16 116.64(11) . . ? O8 C17 O7 122.95(11) . . ? O8 C17 C18 120.96(11) . . ? O7 C17 C18 116.08(10) . . ? 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 O5 Zn1 O1 C6 101.98(8) . . . . ? O2 Zn1 O1 C6 -46.03(18) . . . . ? N1 Zn1 O1 C6 13.93(8) . . . . ? O3 Zn1 O1 C6 -171.03(8) . . . . ? N2 Zn1 O1 C6 -86.99(8) . . . . ? Zn2 Zn1 O1 C6 177.79(6) . . . . ? O5 Zn1 N1 C1 -105.33(8) . . . . ? O2 Zn1 N1 C1 162.61(8) . . . . ? O3 Zn1 N1 C1 -18.12(15) . . . . ? N2 Zn1 N1 C1 83.05(9) . . . . ? O1 Zn1 N1 C1 -5.21(8) . . . . ? Zn2 Zn1 N1 C1 -175.29(6) . . . . ? O5 Zn1 N1 C5 71.19(9) . . . . ? O2 Zn1 N1 C5 -20.87(9) . . . . ? O3 Zn1 N1 C5 158.40(9) . . . . ? N2 Zn1 N1 C5 -100.43(9) . . . . ? O1 Zn1 N1 C5 171.31(9) . . . . ? Zn2 Zn1 N1 C5 1.23(10) . . . . ? C5 N1 C1 C2 0.37(16) . . . . ? Zn1 N1 C1 C2 177.02(8) . . . . ? C5 N1 C1 C6 179.41(10) . . . . ? Zn1 N1 C1 C6 -3.95(13) . . . . ? O5 Zn1 Zn2 O2 -113.20(5) . . . . ? N1 Zn1 Zn2 O2 -36.16(5) . . . . ? O3 Zn1 Zn2 O2 152.92(5) . . . . ? N2 Zn1 Zn2 O2 69.61(5) . . . . ? O1 Zn1 Zn2 O2 164.66(7) . . . . ? O5 Zn1 Zn2 O7 -113.2(3) . . . . ? O2 Zn1 Zn2 O7 0.0(3) . . . . ? N1 Zn1 Zn2 O7 -36.2(3) . . . . ? O3 Zn1 Zn2 O7 152.9(3) . . . . ? N2 Zn1 Zn2 O7 69.6(3) . . . . ? O1 Zn1 Zn2 O7 164.7(3) . . . . ? O5 Zn1 Zn2 O6 8.72(4) . . . . ? O2 Zn1 Zn2 O6 121.92(5) . . . . ? N1 Zn1 Zn2 O6 85.75(5) . . . . ? O3 Zn1 Zn2 O6 -85.17(4) . . . . ? N2 Zn1 Zn2 O6 -168.47(4) . . . . ? O1 Zn1 Zn2 O6 -73.43(6) . . . . ? O5 Zn1 Zn2 O4 121.60(4) . . . . ? O2 Zn1 Zn2 O4 -125.20(5) . . . . ? N1 Zn1 Zn2 O4 -161.36(5) . . . . ? O3 Zn1 Zn2 O4 27.72(4) . . . . ? N2 Zn1 Zn2 O4 -55.58(4) . . . . ? O1 Zn1 Zn2 O4 39.46(6) . . . . ? O7 Zn2 O2 C12 58.98(10) . . . . ? O6 Zn2 O2 C12 178.31(9) . . . . ? O4 Zn2 O2 C12 -63.76(9) . . . . ? Zn1 Zn2 O2 C12 -121.02(10) . . . . ? O7 Zn2 O2 Zn1 180.00(4) . . . . ? O6 Zn2 O2 Zn1 -60.67(5) . . . . ? O4 Zn2 O2 Zn1 57.26(4) . . . . ? O5 Zn1 O2 C12 -171.73(8) . . . . ? N1 Zn1 O2 C12 -80.97(8) . . . . ? O3 Zn1 O2 C12 99.32(8) . . . . ? N2 Zn1 O2 C12 18.78(7) . . . . ? O1 Zn1 O2 C12 -23.20(18) . . . . ? Zn2 Zn1 O2 C12 125.83(9) . . . . ? O5 Zn1 O2 Zn2 62.45(4) . . . . ? N1 Zn1 O2 Zn2 153.21(4) . . . . ? O3 Zn1 O2 Zn2 -26.50(5) . . . . ? N2 Zn1 O2 Zn2 -107.05(4) . . . . ? O1 Zn1 O2 Zn2 -149.03(12) . . . . ? N1 C1 C2 C3 -0.48(17) . . . . ? C6 C1 C2 C3 -179.47(11) . . . . ? O5 Zn1 N2 C7 -54.13(19) . . . . ? O2 Zn1 N2 C7 -5.63(8) . . . . ? N1 Zn1 N2 C7 89.06(8) . . . . ? O3 Zn1 N2 C7 -113.15(8) . . . . ? O1 Zn1 N2 C7 165.05(8) . . . . ? Zn2 Zn1 N2 C7 -42.91(8) . . . . ? O5 Zn1 N2 C11 114.92(17) . . . . ? O2 Zn1 N2 C11 163.42(10) . . . . ? N1 Zn1 N2 C11 -101.89(10) . . . . ? O3 Zn1 N2 C11 55.90(10) . . . . ? O1 Zn1 N2 C11 -25.90(10) . . . . ? Zn2 Zn1 N2 C11 126.14(10) . . . . ? C1 C2 C3 C4 0.34(18) . . . . ? O5 Zn1 O3 C13 -114.76(11) . . . . ? O2 Zn1 O3 C13 -23.13(11) . . . . ? N1 Zn1 O3 C13 157.62(10) . . . . ? N2 Zn1 O3 C13 53.20(10) . . . . ? O1 Zn1 O3 C13 144.98(11) . . . . ? Zn2 Zn1 O3 C13 -40.58(10) . . . . ? O2 Zn2 O4 C13 -64.36(10) . . . . ? O7 Zn2 O4 C13 156.31(9) . . . . ? O6 Zn2 O4 C13 49.56(10) . . . . ? Zn1 Zn2 O4 C13 -28.67(9) . . . . ? C2 C3 C4 C5 -0.12(18) . . . . ? C1 N1 C5 C4 -0.13(17) . . . . ? Zn1 N1 C5 C4 -176.64(9) . . . . ? C3 C4 C5 N1 0.01(18) . . . . ? O2 Zn1 O5 C15 -48.56(11) . . . . ? N1 Zn1 O5 C15 -145.24(11) . . . . ? O3 Zn1 O5 C15 57.28(11) . . . . ? N2 Zn1 O5 C15 -1.3(2) . . . . ? O1 Zn1 O5 C15 138.82(11) . . . . ? Zn2 Zn1 O5 C15 -12.93(10) . . . . ? Zn1 O1 C6 C1 -19.58(12) . . . . ? N1 C1 C6 O1 15.65(14) . . . . ? C2 C1 C6 O1 -165.30(10) . . . . ? O2 Zn2 O6 C15 27.56(11) . . . . ? O7 Zn2 O6 C15 165.33(10) . . . . ? O4 Zn2 O6 C15 -87.00(11) . . . . ? Zn1 Zn2 O6 C15 -9.52(10) . . . . ? C11 N2 C7 C8 1.06(18) . . . . ? Zn1 N2 C7 C8 170.78(10) . . . . ? C11 N2 C7 C12 -177.61(10) . . . . ? Zn1 N2 C7 C12 -7.88(12) . . . . ? O2 Zn2 O7 C17 -28.72(12) . . . . ? O6 Zn2 O7 C17 -149.81(10) . . . . ? O4 Zn2 O7 C17 95.57(10) . . . . ? Zn1 Zn2 O7 C17 -28.7(4) . . . . ? N2 C7 C8 C9 -1.1(2) . . . . ? C12 C7 C8 C9 177.45(13) . . . . ? C7 C8 C9 C10 0.4(2) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C7 N2 C11 C10 -0.30(18) . . . . ? Zn1 N2 C11 C10 -168.89(10) . . . . ? C9 C10 C11 N2 -0.4(2) . . . . ? Zn2 O2 C12 C7 85.06(11) . . . . ? Zn1 O2 C12 C7 -28.00(12) . . . . ? N2 C7 C12 O2 23.98(15) . . . . ? C8 C7 C12 O2 -154.67(12) . . . . ? Zn1 O3 C13 O4 35.77(17) . . . . ? Zn1 O3 C13 C14 -142.10(10) . . . . ? Zn2 O4 C13 O3 8.62(17) . . . . ? Zn2 O4 C13 C14 -173.46(9) . . . . ? Zn1 O5 C15 O6 11.00(19) . . . . ? Zn1 O5 C15 C16 -168.22(9) . . . . ? Zn2 O6 C15 O5 3.80(18) . . . . ? Zn2 O6 C15 C16 -176.98(9) . . . . ? Zn2 O7 C17 O8 4.36(16) . . . . ? Zn2 O7 C17 C18 -174.42(9) . . . . ? _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 38.33 _diffrn_measured_fraction_theta_full 0.890 _refine_diff_density_max 1.383 _refine_diff_density_min -1.405 _refine_diff_density_rms 0.103