# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_MTAF-3 _database_code_depnum_ccdc_archive 'CCDC 878737' #TrackingRef 'MTAF-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common MTAF-3 _chemical_melting_point Not _chemical_formula_moiety '2(C28 H17 N5 O8 Zn2), 2(C5 H11 N O), O' _chemical_formula_sum 'C66 H56 N12 O19 Zn4' _chemical_formula_weight 1582.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 34.6925(7) _cell_length_b 16.6027(4) _cell_length_c 13.7633(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.3030(10) _cell_angle_gamma 90.00 _cell_volume 7646.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 228(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 2.039 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6859 _exptl_absorpt_correction_T_max 0.6859 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 228(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47412 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 68.40 _reflns_number_total 6948 _reflns_number_gt 5801 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _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^)+(0.0622P)^2^+15.5419P] 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 6948 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.007 _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 1.174439(9) 0.254488(17) 1.24412(2) 0.01785(11) Uani 1 1 d . . . Zn2 Zn 1.086229(9) 0.244780(17) 1.18370(2) 0.01807(11) Uani 1 1 d . . . O1 O 1.17212(6) -0.15284(11) 0.82397(16) 0.0395(5) Uani 1 1 d . . . O2 O 1.10560(6) -0.14783(11) 0.77419(17) 0.0440(5) Uani 1 1 d . . . O3 O 1.10388(6) 0.18245(13) 1.07413(16) 0.0417(5) Uani 1 1 d . . . O4 O 1.17021(6) 0.18601(12) 1.12033(15) 0.0368(5) Uani 1 1 d . . . O5 O 1.08784(6) 0.65265(12) 1.60350(16) 0.0384(5) Uani 1 1 d . . . O6 O 1.15427(6) 0.64802(11) 1.65478(15) 0.0372(5) Uani 1 1 d . . . O7 O 1.09062(6) 0.31724(12) 1.30392(15) 0.0352(4) Uani 1 1 d . . . O8 O 1.15731(6) 0.31624(12) 1.35601(15) 0.0373(5) Uani 1 1 d . . . N1 N 1.02780(6) 0.21086(13) 1.13028(17) 0.0282(5) Uani 1 1 d . . . N2 N 0.73381(6) 0.21876(13) 0.78574(16) 0.0249(4) Uani 1 1 d . . . C2 C 1.13886(9) -0.12152(15) 0.8214(2) 0.0303(6) Uani 1 1 d . . . C3 C 1.13750(8) 0.15918(15) 1.06870(19) 0.0272(5) Uani 1 1 d . . . C4 C 1.13840(8) 0.09167(15) 0.9969(2) 0.0287(6) Uani 1 1 d . . . C5 C 1.10284(9) 0.05785(18) 0.9405(2) 0.0397(7) Uani 1 1 d . . . H5 H 1.0783 0.0813 0.9420 0.048 Uiso 1 1 calc R . . C6 C 1.10320(8) -0.00946(18) 0.8826(2) 0.0378(7) Uani 1 1 d . . . H6 H 1.0790 -0.0314 0.8441 0.045 Uiso 1 1 calc R . . C7 C 1.13922(8) -0.04534(15) 0.88065(19) 0.0277(5) Uani 1 1 d . . . C8 C 1.17457(8) -0.01025(17) 0.9338(2) 0.0331(6) Uani 1 1 d . . . H8 H 1.1991 -0.0331 0.9312 0.040 Uiso 1 1 calc R . . C9 C 1.17421(8) 0.05835(16) 0.9908(2) 0.0324(6) Uani 1 1 d . . . H9 H 1.1985 0.0824 1.0257 0.039 Uiso 1 1 calc R . . C10 C 1.12108(8) 0.62177(15) 1.6062(2) 0.0283(6) Uani 1 1 d . . . C11 C 1.12115(8) 0.54670(16) 1.54554(19) 0.0282(6) Uani 1 1 d . . . C12 C 1.08554(8) 0.51260(17) 1.4887(2) 0.0336(6) Uani 1 1 d . . . H12 H 1.0610 0.5355 1.4906 0.040 Uiso 1 1 calc R . . C13 C 1.15722(8) 0.51074(17) 1.5444(2) 0.0331(6) Uani 1 1 d . . . H13 H 1.1814 0.5325 1.5836 0.040 Uiso 1 1 calc R . . C14 C 1.12341(8) 0.34194(15) 1.35767(19) 0.0270(5) Uani 1 1 d . . . C15 C 1.12235(8) 0.41039(15) 1.4277(2) 0.0274(5) Uani 1 1 d . . . C16 C 1.15777(8) 0.44321(16) 1.4861(2) 0.0316(6) Uani 1 1 d . . . H16 H 1.1823 0.4193 1.4860 0.038 Uiso 1 1 calc R . . C17 C 1.08615(8) 0.44576(16) 1.4302(2) 0.0339(6) Uani 1 1 d . . . H17 H 1.0620 0.4237 1.3915 0.041 Uiso 1 1 calc R . . C18 C 1.02022(9) 0.13531(18) 1.1010(3) 0.0549(10) Uani 1 1 d . . . H18 H 1.0408 0.0971 1.1206 0.066 Uiso 1 1 calc R . . C19 C 0.98354(9) 0.11003(19) 1.0432(3) 0.0588(11) Uani 1 1 d . . . H19 H 0.9794 0.0560 1.0227 0.071 Uiso 1 1 calc R . . C20 C 0.95301(7) 0.16545(17) 1.0160(2) 0.0325(6) Uani 1 1 d . . . C21 C 0.96012(9) 0.24283(19) 1.0507(3) 0.0471(9) Uani 1 1 d . . . H21 H 0.9397 0.2816 1.0359 0.057 Uiso 1 1 calc R . . C22 C 0.99771(8) 0.26253(18) 1.1074(3) 0.0418(8) Uani 1 1 d . . . H22 H 1.0024 0.3156 1.1314 0.050 Uiso 1 1 calc R . . N23 N 0.91547(7) 0.14262(14) 0.9524(2) 0.0379(6) Uani 1 1 d . . . N24 N 0.88221(6) 0.18569(14) 0.94531(18) 0.0332(5) Uani 1 1 d . . . C25 C 0.85457(7) 0.14615(17) 0.8766(2) 0.0309(6) Uani 1 1 d . . . C26 C 0.87152(10) 0.0798(2) 0.8434(3) 0.0552(10) Uani 1 1 d . . . H26 H 0.8581 0.0429 0.7944 0.066 Uiso 1 1 calc R . . N27 N 0.91045(8) 0.07688(19) 0.8930(3) 0.0618(9) Uani 1 1 d . . . C28 C 0.81317(7) 0.17221(17) 0.8455(2) 0.0303(6) Uani 1 1 d . . . C29 C 0.79719(8) 0.22015(18) 0.9072(2) 0.0331(6) Uani 1 1 d . . . H29 H 0.8130 0.2372 0.9704 0.040 Uiso 1 1 calc R . . C30 C 0.75757(8) 0.24241(17) 0.8740(2) 0.0299(6) Uani 1 1 d . . . H30 H 0.7468 0.2758 0.9155 0.036 Uiso 1 1 calc R . . C31 C 0.74958(8) 0.1744(2) 0.7250(2) 0.0402(7) Uani 1 1 d . . . H31 H 0.7333 0.1591 0.6616 0.048 Uiso 1 1 calc R . . C32 C 0.78913(8) 0.1501(2) 0.7523(2) 0.0446(8) Uani 1 1 d . . . H32 H 0.7995 0.1190 0.7080 0.054 Uiso 1 1 calc R . . O33 O 0.73587(11) 0.1222(4) 0.4990(3) 0.136(2) Uani 1 1 d . . . C34 C 0.70660(17) 0.1469(5) 0.4332(5) 0.107(2) Uani 1 1 d . . . H34 H 0.6929 0.1924 0.4477 0.128 Uiso 1 1 calc R . . N35 N 0.69332(13) 0.1125(3) 0.3421(3) 0.0901(13) Uani 1 1 d . . . C36 C 0.65829(19) 0.1433(4) 0.2695(5) 0.113(2) Uani 1 1 d . . . H36A H 0.6638 0.1462 0.2033 0.135 Uiso 1 1 calc R . . H36B H 0.6530 0.1981 0.2889 0.135 Uiso 1 1 calc R . . C37 C 0.62226(18) 0.0933(5) 0.2614(5) 0.120(2) Uani 1 1 d . . . H37A H 0.6276 0.0385 0.2445 0.181 Uiso 1 1 calc R . . H37B H 0.6002 0.1150 0.2092 0.181 Uiso 1 1 calc R . . H37C H 0.6153 0.0938 0.3252 0.181 Uiso 1 1 calc R . . C38 C 0.74183(16) 0.0621(3) 0.2517(4) 0.0894(15) Uani 1 1 d . . . H38A H 0.7266 0.0869 0.1896 0.134 Uiso 1 1 calc R . . H38B H 0.7552 0.0145 0.2362 0.134 Uiso 1 1 calc R . . H38C H 0.7616 0.1001 0.2887 0.134 Uiso 1 1 calc R . . C39 C 0.71416(15) 0.0389(3) 0.3145(4) 0.0786(13) Uani 1 1 d . . . H39A H 0.7294 0.0121 0.3761 0.094 Uiso 1 1 calc R . . H39B H 0.6941 0.0008 0.2769 0.094 Uiso 1 1 calc R . . O10 O 1.0202(3) 0.4583(7) 1.1684(10) 0.154(4) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01181(17) 0.01716(17) 0.02218(19) -0.00069(11) 0.00028(13) -0.00078(10) Zn2 0.01160(17) 0.01699(17) 0.02287(19) -0.00106(11) -0.00029(13) -0.00092(10) O1 0.0410(12) 0.0277(10) 0.0529(13) -0.0180(9) 0.0180(10) -0.0043(9) O2 0.0441(12) 0.0270(10) 0.0483(12) -0.0169(9) -0.0097(10) 0.0025(9) O3 0.0315(11) 0.0468(12) 0.0454(12) -0.0228(10) 0.0079(9) 0.0034(9) O4 0.0300(10) 0.0383(11) 0.0382(11) -0.0185(9) 0.0022(8) 0.0013(8) O5 0.0365(11) 0.0295(10) 0.0484(12) -0.0172(9) 0.0099(9) 0.0000(8) O6 0.0352(11) 0.0262(9) 0.0415(11) -0.0138(8) -0.0053(9) -0.0002(8) O7 0.0373(11) 0.0339(10) 0.0334(10) -0.0131(8) 0.0077(9) -0.0033(8) O8 0.0374(11) 0.0361(11) 0.0385(11) -0.0137(9) 0.0105(9) 0.0041(9) N1 0.0153(10) 0.0272(11) 0.0389(12) -0.0020(10) 0.0014(9) -0.0020(8) N2 0.0146(10) 0.0278(11) 0.0290(11) -0.0001(9) -0.0002(8) -0.0001(8) C2 0.0420(16) 0.0207(12) 0.0268(13) -0.0009(10) 0.0068(12) -0.0028(11) C3 0.0293(14) 0.0246(12) 0.0253(13) -0.0025(10) 0.0029(11) 0.0003(10) C4 0.0296(14) 0.0253(13) 0.0288(13) -0.0055(11) 0.0036(11) 0.0016(10) C5 0.0277(14) 0.0420(16) 0.0450(17) -0.0178(14) 0.0017(12) 0.0041(12) C6 0.0281(14) 0.0393(15) 0.0409(16) -0.0157(13) 0.0001(12) -0.0032(12) C7 0.0329(14) 0.0224(12) 0.0264(13) -0.0021(10) 0.0054(11) 0.0009(10) C8 0.0281(14) 0.0311(14) 0.0397(16) -0.0097(12) 0.0083(12) 0.0023(11) C9 0.0264(13) 0.0318(14) 0.0365(15) -0.0119(12) 0.0037(11) -0.0042(11) C10 0.0358(15) 0.0214(12) 0.0270(13) -0.0007(10) 0.0073(11) 0.0004(11) C11 0.0309(14) 0.0226(12) 0.0297(13) -0.0049(10) 0.0058(11) -0.0020(10) C12 0.0263(14) 0.0299(14) 0.0438(16) -0.0105(12) 0.0078(12) 0.0002(11) C13 0.0264(13) 0.0326(14) 0.0354(15) -0.0087(12) -0.0004(11) -0.0025(11) C14 0.0349(15) 0.0224(12) 0.0250(13) -0.0013(10) 0.0099(11) -0.0028(11) C15 0.0309(14) 0.0223(12) 0.0287(13) -0.0034(10) 0.0073(11) -0.0014(10) C16 0.0259(13) 0.0305(14) 0.0365(15) -0.0079(12) 0.0048(11) 0.0041(11) C17 0.0276(14) 0.0306(14) 0.0416(16) -0.0142(12) 0.0059(12) -0.0066(11) C18 0.0212(15) 0.0298(15) 0.097(3) 0.0012(16) -0.0142(16) 0.0023(12) C19 0.0233(15) 0.0275(15) 0.108(3) -0.0106(18) -0.0127(17) -0.0001(12) C20 0.0127(12) 0.0350(14) 0.0462(16) -0.0031(13) 0.0014(11) -0.0007(10) C21 0.0188(14) 0.0421(17) 0.072(2) -0.0182(16) -0.0030(14) 0.0095(12) C22 0.0169(13) 0.0364(15) 0.066(2) -0.0230(15) -0.0004(13) 0.0035(11) N23 0.0177(11) 0.0375(13) 0.0544(15) -0.0091(12) 0.0023(10) 0.0005(9) N24 0.0145(10) 0.0364(13) 0.0437(14) -0.0042(10) -0.0009(9) 0.0030(9) C25 0.0126(12) 0.0377(15) 0.0378(15) -0.0058(12) -0.0015(10) -0.0005(10) C26 0.0316(17) 0.057(2) 0.072(2) -0.0350(19) 0.0050(16) -0.0067(15) N27 0.0332(15) 0.0576(18) 0.090(2) -0.0309(18) 0.0081(15) -0.0002(13) C28 0.0155(12) 0.0350(14) 0.0363(15) -0.0019(12) -0.0004(10) 0.0000(10) C29 0.0182(13) 0.0466(16) 0.0279(14) -0.0055(12) -0.0058(10) 0.0029(12) C30 0.0220(13) 0.0399(15) 0.0259(13) -0.0052(11) 0.0028(11) 0.0026(11) C31 0.0218(13) 0.0555(19) 0.0366(16) -0.0184(14) -0.0043(12) 0.0033(13) C32 0.0213(14) 0.062(2) 0.0464(18) -0.0251(16) 0.0007(12) 0.0074(13) O33 0.059(2) 0.270(6) 0.078(2) -0.063(3) 0.0176(18) -0.010(3) C34 0.073(4) 0.158(6) 0.095(4) -0.026(4) 0.029(3) -0.032(4) N35 0.084(3) 0.122(4) 0.059(2) 0.000(2) 0.010(2) -0.027(3) C36 0.107(5) 0.123(5) 0.104(4) 0.033(4) 0.021(4) -0.010(4) C37 0.090(4) 0.174(7) 0.094(4) 0.025(4) 0.018(3) -0.012(4) C38 0.092(4) 0.088(3) 0.080(3) 0.003(3) 0.007(3) -0.028(3) C39 0.089(3) 0.076(3) 0.067(3) -0.007(2) 0.015(2) -0.026(3) O10 0.089(6) 0.160(9) 0.207(12) -0.014(9) 0.028(7) 0.007(6) _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 O4 2.0212(19) . ? Zn1 O1 2.0271(18) 6_556 ? Zn1 N2 2.036(2) 8_556 ? Zn1 O6 2.0415(18) 6_565 ? Zn1 O8 2.0636(19) . ? Zn1 Zn2 2.9562(4) . ? Zn2 O7 2.0188(18) . ? Zn2 O2 2.0376(18) 6_556 ? Zn2 O5 2.0381(18) 6_565 ? Zn2 N1 2.045(2) . ? Zn2 O3 2.0512(19) . ? O1 C2 1.257(3) . ? O1 Zn1 2.0271(18) 6 ? O2 C2 1.244(3) . ? O2 Zn2 2.0376(18) 6 ? O3 C3 1.250(3) . ? O4 C3 1.251(3) . ? O5 C10 1.254(3) . ? O5 Zn2 2.0381(18) 6_566 ? O6 C10 1.247(3) . ? O6 Zn1 2.0415(18) 6_566 ? O7 C14 1.251(3) . ? O8 C14 1.257(3) . ? N1 C18 1.322(4) . ? N1 C22 1.323(4) . ? N2 C30 1.335(3) . ? N2 C31 1.335(4) . ? N2 Zn1 2.036(2) 8_455 ? C2 C7 1.503(4) . ? C3 C4 1.500(4) . ? C4 C9 1.382(4) . ? C4 C5 1.391(4) . ? C5 C6 1.374(4) . ? C5 H5 0.9400 . ? C6 C7 1.391(4) . ? C6 H6 0.9400 . ? C7 C8 1.380(4) . ? C8 C9 1.385(4) . ? C8 H8 0.9400 . ? C9 H9 0.9400 . ? C10 C11 1.501(4) . ? C11 C13 1.390(4) . ? C11 C12 1.396(4) . ? C12 C17 1.375(4) . ? C12 H12 0.9400 . ? C13 C16 1.382(4) . ? C13 H13 0.9400 . ? C14 C15 1.496(4) . ? C15 C16 1.390(4) . ? C15 C17 1.395(4) . ? C16 H16 0.9400 . ? C17 H17 0.9400 . ? C18 C19 1.376(4) . ? C18 H18 0.9400 . ? C19 C20 1.378(4) . ? C19 H19 0.9400 . ? C20 C21 1.370(4) . ? C20 N23 1.416(3) . ? C21 C22 1.371(4) . ? C21 H21 0.9400 . ? C22 H22 0.9400 . ? N23 N24 1.339(3) . ? N23 N27 1.347(4) . ? N24 C25 1.329(3) . ? C25 C26 1.381(4) . ? C25 C28 1.452(3) . ? C26 N27 1.344(4) . ? C26 H26 0.9400 . ? C28 C32 1.382(4) . ? C28 C29 1.383(4) . ? C29 C30 1.380(4) . ? C29 H29 0.9400 . ? C30 H30 0.9400 . ? C31 C32 1.383(4) . ? C31 H31 0.9400 . ? C32 H32 0.9400 . ? O33 C34 1.239(7) . ? C34 N35 1.343(7) . ? C34 H34 0.9400 . ? N35 C36 1.448(7) . ? N35 C39 1.518(7) . ? C36 C37 1.480(8) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C37 H37C 0.9700 . ? C38 C39 1.502(7) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C38 H38C 0.9700 . ? C39 H39A 0.9800 . ? C39 H39B 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 O4 Zn1 O1 89.10(9) . 6_556 ? O4 Zn1 N2 101.70(8) . 8_556 ? O1 Zn1 N2 102.19(9) 6_556 8_556 ? O4 Zn1 O6 90.07(9) . 6_565 ? O1 Zn1 O6 158.48(8) 6_556 6_565 ? N2 Zn1 O6 99.03(8) 8_556 6_565 ? O4 Zn1 O8 159.61(8) . . ? O1 Zn1 O8 87.05(8) 6_556 . ? N2 Zn1 O8 98.68(8) 8_556 . ? O6 Zn1 O8 86.28(9) 6_565 . ? O4 Zn1 Zn2 83.84(6) . . ? O1 Zn1 Zn2 85.46(6) 6_556 . ? N2 Zn1 Zn2 170.52(6) 8_556 . ? O6 Zn1 Zn2 73.08(6) 6_565 . ? O8 Zn1 Zn2 75.90(6) . . ? O7 Zn2 O2 91.63(9) . 6_556 ? O7 Zn2 O5 86.51(9) . 6_565 ? O2 Zn2 O5 159.93(9) 6_556 6_565 ? O7 Zn2 N1 108.18(9) . . ? O2 Zn2 N1 97.93(9) 6_556 . ? O5 Zn2 N1 101.64(9) 6_565 . ? O7 Zn2 O3 158.54(8) . . ? O2 Zn2 O3 86.36(10) 6_556 . ? O5 Zn2 O3 88.12(9) 6_565 . ? N1 Zn2 O3 93.25(9) . . ? O7 Zn2 Zn1 83.59(6) . . ? O2 Zn2 Zn1 73.81(6) 6_556 . ? O5 Zn2 Zn1 86.13(6) 6_565 . ? N1 Zn2 Zn1 166.09(6) . . ? O3 Zn2 Zn1 75.32(6) . . ? C2 O1 Zn1 119.76(18) . 6 ? C2 O2 Zn2 135.00(19) . 6 ? C3 O3 Zn2 131.64(18) . . ? C3 O4 Zn1 122.16(18) . . ? C10 O5 Zn2 118.83(17) . 6_566 ? C10 O6 Zn1 136.14(18) . 6_566 ? C14 O7 Zn2 122.68(18) . . ? C14 O8 Zn1 129.59(18) . . ? C18 N1 C22 117.5(2) . . ? C18 N1 Zn2 118.00(18) . . ? C22 N1 Zn2 123.50(19) . . ? C30 N2 C31 118.4(2) . . ? C30 N2 Zn1 121.85(18) . 8_455 ? C31 N2 Zn1 119.70(17) . 8_455 ? O2 C2 O1 126.0(2) . . ? O2 C2 C7 116.9(2) . . ? O1 C2 C7 117.2(2) . . ? O3 C3 O4 125.2(2) . . ? O3 C3 C4 116.9(2) . . ? O4 C3 C4 117.8(2) . . ? C9 C4 C5 118.9(2) . . ? C9 C4 C3 120.9(2) . . ? C5 C4 C3 120.0(2) . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.1(2) . . ? C8 C7 C2 121.5(2) . . ? C6 C7 C2 119.5(2) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C4 C9 C8 120.4(2) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? O6 C10 O5 125.8(2) . . ? O6 C10 C11 116.8(2) . . ? O5 C10 C11 117.4(2) . . ? C13 C11 C12 119.1(2) . . ? C13 C11 C10 119.8(2) . . ? C12 C11 C10 121.1(2) . . ? C17 C12 C11 120.5(3) . . ? C17 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C16 C13 C11 120.3(2) . . ? C16 C13 H13 119.8 . . ? C11 C13 H13 119.8 . . ? O7 C14 O8 125.9(2) . . ? O7 C14 C15 117.2(2) . . ? O8 C14 C15 116.9(2) . . ? C16 C15 C17 119.0(2) . . ? C16 C15 C14 120.1(2) . . ? C17 C15 C14 120.7(2) . . ? C13 C16 C15 120.6(2) . . ? C13 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C12 C17 C15 120.5(3) . . ? C12 C17 H17 119.8 . . ? C15 C17 H17 119.8 . . ? N1 C18 C19 123.0(3) . . ? N1 C18 H18 118.5 . . ? C19 C18 H18 118.5 . . ? C18 C19 C20 118.7(3) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C21 C20 C19 118.5(3) . . ? C21 C20 N23 121.2(2) . . ? C19 C20 N23 120.3(3) . . ? C20 C21 C22 118.6(3) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? N1 C22 C21 123.6(3) . . ? N1 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? N24 N23 N27 114.7(2) . . ? N24 N23 C20 122.4(2) . . ? N27 N23 C20 122.9(2) . . ? C25 N24 N23 103.5(2) . . ? N24 C25 C26 109.8(2) . . ? N24 C25 C28 122.3(2) . . ? C26 C25 C28 127.9(3) . . ? N27 C26 C25 108.6(3) . . ? N27 C26 H26 125.7 . . ? C25 C26 H26 125.7 . . ? C26 N27 N23 103.3(3) . . ? C32 C28 C29 118.8(2) . . ? C32 C28 C25 120.2(3) . . ? C29 C28 C25 121.1(2) . . ? C30 C29 C28 118.5(2) . . ? C30 C29 H29 120.8 . . ? C28 C29 H29 120.8 . . ? N2 C30 C29 123.0(3) . . ? N2 C30 H30 118.5 . . ? C29 C30 H30 118.5 . . ? N2 C31 C32 122.1(3) . . ? N2 C31 H31 119.0 . . ? C32 C31 H31 119.0 . . ? C28 C32 C31 119.2(3) . . ? C28 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? O33 C34 N35 123.7(7) . . ? O33 C34 H34 118.2 . . ? N35 C34 H34 118.2 . . ? C34 N35 C36 120.8(6) . . ? C34 N35 C39 120.5(5) . . ? C36 N35 C39 118.7(5) . . ? N35 C36 C37 113.1(5) . . ? N35 C36 H36A 109.0 . . ? C37 C36 H36A 109.0 . . ? N35 C36 H36B 109.0 . . ? C37 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 C38 H38A 109.5 . . ? C39 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C39 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C38 C39 N35 110.9(4) . . ? C38 C39 H39A 109.5 . . ? N35 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? N35 C39 H39B 109.5 . . ? H39A C39 H39B 108.1 . . ? 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 O4 Zn1 Zn2 O7 -177.64(8) . . . . ? O1 Zn1 Zn2 O7 92.78(9) 6_556 . . . ? O6 Zn1 Zn2 O7 -85.68(9) 6_565 . . . ? O8 Zn1 Zn2 O7 4.69(8) . . . . ? O4 Zn1 Zn2 O2 88.79(9) . . . 6_556 ? O1 Zn1 Zn2 O2 -0.79(9) 6_556 . . 6_556 ? O6 Zn1 Zn2 O2 -179.26(9) 6_565 . . 6_556 ? O8 Zn1 Zn2 O2 -88.89(9) . . . 6_556 ? O4 Zn1 Zn2 O5 -90.72(9) . . . 6_565 ? O1 Zn1 Zn2 O5 179.70(9) 6_556 . . 6_565 ? O6 Zn1 Zn2 O5 1.23(9) 6_565 . . 6_565 ? O8 Zn1 Zn2 O5 91.60(9) . . . 6_565 ? O4 Zn1 Zn2 N1 33.9(3) . . . . ? O1 Zn1 Zn2 N1 -55.7(3) 6_556 . . . ? O6 Zn1 Zn2 N1 125.8(3) 6_565 . . . ? O8 Zn1 Zn2 N1 -143.8(3) . . . . ? O4 Zn1 Zn2 O3 -1.65(9) . . . . ? O1 Zn1 Zn2 O3 -91.24(9) 6_556 . . . ? O6 Zn1 Zn2 O3 90.30(9) 6_565 . . . ? O8 Zn1 Zn2 O3 -179.33(9) . . . . ? O7 Zn2 O3 C3 21.3(4) . . . . ? O2 Zn2 O3 C3 -63.9(3) 6_556 . . . ? O5 Zn2 O3 C3 96.8(3) 6_565 . . . ? N1 Zn2 O3 C3 -161.7(3) . . . . ? Zn1 Zn2 O3 C3 10.3(2) . . . . ? O1 Zn1 O4 C3 80.5(2) 6_556 . . . ? N2 Zn1 O4 C3 -177.3(2) 8_556 . . . ? O6 Zn1 O4 C3 -78.0(2) 6_565 . . . ? O8 Zn1 O4 C3 1.4(4) . . . . ? Zn2 Zn1 O4 C3 -5.0(2) . . . . ? O2 Zn2 O7 C14 74.9(2) 6_556 . . . ? O5 Zn2 O7 C14 -85.1(2) 6_565 . . . ? N1 Zn2 O7 C14 173.8(2) . . . . ? O3 Zn2 O7 C14 -9.3(4) . . . . ? Zn1 Zn2 O7 C14 1.4(2) . . . . ? O4 Zn1 O8 C14 -20.6(4) . . . . ? O1 Zn1 O8 C14 -100.1(2) 6_556 . . . ? N2 Zn1 O8 C14 158.1(2) 8_556 . . . ? O6 Zn1 O8 C14 59.5(2) 6_565 . . . ? Zn2 Zn1 O8 C14 -14.0(2) . . . . ? O7 Zn2 N1 C18 -139.1(3) . . . . ? O2 Zn2 N1 C18 -44.8(3) 6_556 . . . ? O5 Zn2 N1 C18 130.8(3) 6_565 . . . ? O3 Zn2 N1 C18 42.0(3) . . . . ? Zn1 Zn2 N1 C18 7.8(5) . . . . ? O7 Zn2 N1 C22 52.7(3) . . . . ? O2 Zn2 N1 C22 147.1(3) 6_556 . . . ? O5 Zn2 N1 C22 -37.4(3) 6_565 . . . ? O3 Zn2 N1 C22 -126.1(3) . . . . ? Zn1 Zn2 N1 C22 -160.4(2) . . . . ? Zn2 O2 C2 O1 0.0(5) 6 . . . ? Zn2 O2 C2 C7 -179.91(19) 6 . . . ? Zn1 O1 C2 O2 1.2(4) 6 . . . ? Zn1 O1 C2 C7 -178.87(17) 6 . . . ? Zn2 O3 C3 O4 -18.6(4) . . . . ? Zn2 O3 C3 C4 159.17(19) . . . . ? Zn1 O4 C3 O3 14.2(4) . . . . ? Zn1 O4 C3 C4 -163.47(18) . . . . ? O3 C3 C4 C9 -175.6(3) . . . . ? O4 C3 C4 C9 2.4(4) . . . . ? O3 C3 C4 C5 -0.2(4) . . . . ? O4 C3 C4 C5 177.7(3) . . . . ? C9 C4 C5 C6 2.4(5) . . . . ? C3 C4 C5 C6 -173.0(3) . . . . ? C4 C5 C6 C7 0.8(5) . . . . ? C5 C6 C7 C8 -3.0(5) . . . . ? C5 C6 C7 C2 176.7(3) . . . . ? O2 C2 C7 C8 -178.6(3) . . . . ? O1 C2 C7 C8 1.5(4) . . . . ? O2 C2 C7 C6 1.7(4) . . . . ? O1 C2 C7 C6 -178.2(3) . . . . ? C6 C7 C8 C9 2.0(4) . . . . ? C2 C7 C8 C9 -177.7(3) . . . . ? C5 C4 C9 C8 -3.5(4) . . . . ? C3 C4 C9 C8 171.9(3) . . . . ? C7 C8 C9 C4 1.3(4) . . . . ? Zn1 O6 C10 O5 -2.6(5) 6_566 . . . ? Zn1 O6 C10 C11 177.16(19) 6_566 . . . ? Zn2 O5 C10 O6 0.3(4) 6_566 . . . ? Zn2 O5 C10 C11 -179.47(18) 6_566 . . . ? O6 C10 C11 C13 -0.9(4) . . . . ? O5 C10 C11 C13 178.9(3) . . . . ? O6 C10 C11 C12 179.9(3) . . . . ? O5 C10 C11 C12 -0.3(4) . . . . ? C13 C11 C12 C17 -1.9(4) . . . . ? C10 C11 C12 C17 177.2(3) . . . . ? C12 C11 C13 C16 1.4(4) . . . . ? C10 C11 C13 C16 -177.7(3) . . . . ? Zn2 O7 C14 O8 -12.3(4) . . . . ? Zn2 O7 C14 C15 165.29(17) . . . . ? Zn1 O8 C14 O7 21.0(4) . . . . ? Zn1 O8 C14 C15 -156.53(18) . . . . ? O7 C14 C15 C16 -177.1(2) . . . . ? O8 C14 C15 C16 0.7(4) . . . . ? O7 C14 C15 C17 -1.5(4) . . . . ? O8 C14 C15 C17 176.3(3) . . . . ? C11 C13 C16 C15 0.1(4) . . . . ? C17 C15 C16 C13 -1.2(4) . . . . ? C14 C15 C16 C13 174.4(3) . . . . ? C11 C12 C17 C15 0.9(5) . . . . ? C16 C15 C17 C12 0.7(4) . . . . ? C14 C15 C17 C12 -174.9(3) . . . . ? C22 N1 C18 C19 4.3(6) . . . . ? Zn2 N1 C18 C19 -164.6(3) . . . . ? N1 C18 C19 C20 -1.3(7) . . . . ? C18 C19 C20 C21 -2.3(6) . . . . ? C18 C19 C20 N23 176.8(4) . . . . ? C19 C20 C21 C22 2.7(6) . . . . ? N23 C20 C21 C22 -176.4(3) . . . . ? C18 N1 C22 C21 -3.8(6) . . . . ? Zn2 N1 C22 C21 164.4(3) . . . . ? C20 C21 C22 N1 0.4(6) . . . . ? C21 C20 N23 N24 -19.4(5) . . . . ? C19 C20 N23 N24 161.5(3) . . . . ? C21 C20 N23 N27 159.5(4) . . . . ? C19 C20 N23 N27 -19.6(5) . . . . ? N27 N23 N24 C25 -1.0(4) . . . . ? C20 N23 N24 C25 177.9(3) . . . . ? N23 N24 C25 C26 0.2(4) . . . . ? N23 N24 C25 C28 179.7(3) . . . . ? N24 C25 C26 N27 0.7(4) . . . . ? C28 C25 C26 N27 -178.7(3) . . . . ? C25 C26 N27 N23 -1.3(4) . . . . ? N24 N23 N27 C26 1.5(4) . . . . ? C20 N23 N27 C26 -177.4(3) . . . . ? N24 C25 C28 C32 156.1(3) . . . . ? C26 C25 C28 C32 -24.5(5) . . . . ? N24 C25 C28 C29 -23.0(4) . . . . ? C26 C25 C28 C29 156.4(4) . . . . ? C32 C28 C29 C30 1.5(4) . . . . ? C25 C28 C29 C30 -179.4(3) . . . . ? C31 N2 C30 C29 -2.9(4) . . . . ? Zn1 N2 C30 C29 175.1(2) 8_455 . . . ? C28 C29 C30 N2 1.1(4) . . . . ? C30 N2 C31 C32 2.3(5) . . . . ? Zn1 N2 C31 C32 -175.8(3) 8_455 . . . ? C29 C28 C32 C31 -2.1(5) . . . . ? C25 C28 C32 C31 178.8(3) . . . . ? N2 C31 C32 C28 0.2(5) . . . . ? O33 C34 N35 C36 178.4(6) . . . . ? O33 C34 N35 C39 0.1(9) . . . . ? C34 N35 C36 C37 -103.4(7) . . . . ? C39 N35 C36 C37 74.9(7) . . . . ? C34 N35 C39 C38 -99.5(6) . . . . ? C36 N35 C39 C38 82.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 68.40 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.722 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.075 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.755 0.250 274 64 ' ' 2 0.500 0.255 0.250 274 64 ' ' 3 0.000 0.245 0.750 274 64 ' ' 4 0.500 0.745 0.750 274 64 ' ' _platon_squeeze_details ; ;