# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3320 #TrackingRef '3320.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C65 H38 Mn2 N8 O9, 2(H2 O)' _chemical_formula_sum 'C65 H42 Mn2 N8 O11' _chemical_formula_weight 1220.95 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/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 24.460(4) _cell_length_b 9.9842(14) _cell_length_c 23.479(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.705(3) _cell_angle_gamma 90.00 _cell_volume 5363.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 489 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 16.85 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2504 _exptl_absorpt_coefficient_mu 0.547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7950 _exptl_absorpt_correction_T_max 0.8939 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13329 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4710 _reflns_number_gt 3650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2009)' _computing_cell_refinement 'APEX 2' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2009)' _computing_publication_material 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^)+(0.0752P)^2^+2.5425P] 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 4710 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Mn1 Mn 0.172205(18) 0.27736(4) 0.552097(19) 0.02832(16) Uani 1 1 d . . . N1 N 0.18095(10) 0.1262(2) 0.62838(10) 0.0302(5) Uani 1 1 d . . . N2 N 0.15751(10) 0.3902(2) 0.63243(11) 0.0325(6) Uani 1 1 d . . . N3 N 0.06459(11) 0.2636(2) 0.51597(12) 0.0361(6) Uani 1 1 d . . . N4 N 0.13870(10) 0.1054(2) 0.48275(10) 0.0290(5) Uani 1 1 d . . . O1 O 0.5000 0.4370(4) 0.7500 0.0588(10) Uani 1 2 d S . . O2 O 0.28060(10) 0.3478(2) 0.63757(11) 0.0553(7) Uani 1 1 d . . . O3 O 0.25801(8) 0.2029(2) 0.56253(9) 0.0338(5) Uani 1 1 d . . . O4 O 0.16911(9) 0.4522(2) 0.50093(8) 0.0367(5) Uani 1 1 d . . . O5 O 0.18957(10) 0.5857(2) 0.43532(10) 0.0493(6) Uani 1 1 d . . . C1 C 0.19754(13) 0.0006(3) 0.62809(14) 0.0371(7) Uani 1 1 d . . . H1 H 0.2042 -0.0310 0.5939 0.044 Uiso 1 1 calc R . . C2 C 0.20550(13) -0.0870(3) 0.67632(15) 0.0420(8) Uani 1 1 d . . . H2 H 0.2168 -0.1751 0.6738 0.050 Uiso 1 1 calc R . . C3 C 0.19661(14) -0.0433(3) 0.72745(15) 0.0431(8) Uani 1 1 d . . . H3 H 0.2019 -0.1007 0.7601 0.052 Uiso 1 1 calc R . . C4 C 0.17937(13) 0.0904(3) 0.72969(14) 0.0372(7) Uani 1 1 d . . . C5 C 0.17045(16) 0.1462(4) 0.78164(15) 0.0521(9) Uani 1 1 d . . . H5 H 0.1741 0.0917 0.8149 0.063 Uiso 1 1 calc R . . C6 C 0.15677(16) 0.2764(4) 0.78328(16) 0.0516(9) Uani 1 1 d . . . H6 H 0.1510 0.3101 0.8176 0.062 Uiso 1 1 calc R . . C7 C 0.15096(14) 0.3643(3) 0.73294(14) 0.0396(8) Uani 1 1 d . . . C8 C 0.14023(16) 0.5018(4) 0.73346(17) 0.0523(9) Uani 1 1 d . . . H8 H 0.1335 0.5399 0.7665 0.063 Uiso 1 1 calc R . . C9 C 0.13966(16) 0.5789(3) 0.68643(18) 0.0541(10) Uani 1 1 d . . . H9 H 0.1330 0.6705 0.6870 0.065 Uiso 1 1 calc R . . C10 C 0.14927(14) 0.5202(3) 0.63625(16) 0.0449(8) Uani 1 1 d . . . H10 H 0.1498 0.5752 0.6045 0.054 Uiso 1 1 calc R . . C11 C 0.15927(12) 0.3135(3) 0.68108(13) 0.0302(6) Uani 1 1 d . . . C12 C 0.17288(12) 0.1724(3) 0.67913(13) 0.0300(6) Uani 1 1 d . . . C13 C 0.02792(14) 0.3384(3) 0.53194(16) 0.0482(9) Uani 1 1 d . . . H13 H 0.0436 0.4049 0.5609 0.058 Uiso 1 1 calc R . . C14 C -0.03294(15) 0.3244(4) 0.50826(18) 0.0527(9) Uani 1 1 d . . . H14 H -0.0567 0.3802 0.5212 0.063 Uiso 1 1 calc R . . C15 C -0.05656(14) 0.2274(3) 0.46590(17) 0.0473(9) Uani 1 1 d . . . H15 H -0.0969 0.2156 0.4497 0.057 Uiso 1 1 calc R . . C16 C -0.01996(13) 0.1454(3) 0.44681(14) 0.0383(7) Uani 1 1 d . . . C17 C -0.04098(14) 0.0435(4) 0.40217(16) 0.0507(9) Uani 1 1 d . . . H17 H -0.0811 0.0307 0.3839 0.061 Uiso 1 1 calc R . . C18 C -0.00490(14) -0.0343(4) 0.38569(16) 0.0499(9) Uani 1 1 d . . . H18 H -0.0202 -0.1003 0.3564 0.060 Uiso 1 1 calc R . . C19 C 0.05738(13) -0.0176(3) 0.41270(14) 0.0365(7) Uani 1 1 d . . . C20 C 0.09693(14) -0.1004(3) 0.39830(15) 0.0444(8) Uani 1 1 d . . . H20 H 0.0832 -0.1688 0.3699 0.053 Uiso 1 1 calc R . . C21 C 0.15519(14) -0.0804(3) 0.42590(14) 0.0395(7) Uani 1 1 d . . . H21 H 0.1819 -0.1356 0.4173 0.047 Uiso 1 1 calc R . . C22 C 0.17439(13) 0.0247(3) 0.46761(13) 0.0324(7) Uani 1 1 d . . . H22 H 0.2144 0.0387 0.4857 0.039 Uiso 1 1 calc R . . C23 C 0.08014(12) 0.0835(3) 0.45587(12) 0.0296(6) Uani 1 1 d . . . C24 C 0.04109(12) 0.1672(3) 0.47347(13) 0.0314(7) Uani 1 1 d . . . C25 C 0.5000 0.3159(5) 0.7500 0.0416(11) Uani 1 2 d S . . C26 C 0.45574(13) 0.2373(3) 0.70022(14) 0.0383(7) Uani 1 1 d . . . C27 C 0.47200(14) 0.1229(4) 0.67729(16) 0.0522(9) Uani 1 1 d . . . H27 H 0.5102 0.0915 0.6939 0.063 Uiso 1 1 calc R . . C28 C 0.43141(14) 0.0548(4) 0.62956(15) 0.0493(9) Uani 1 1 d . . . H28 H 0.4430 -0.0208 0.6136 0.059 Uiso 1 1 calc R . . C29 C 0.37364(12) 0.0975(3) 0.60504(12) 0.0308(7) Uani 1 1 d . . . C30 C 0.35649(12) 0.2102(3) 0.63017(12) 0.0269(6) Uani 1 1 d . . . C31 C 0.39845(12) 0.2792(3) 0.67662(13) 0.0314(7) Uani 1 1 d . . . H31 H 0.3875 0.3561 0.6923 0.038 Uiso 1 1 calc R . . C32 C 0.29354(12) 0.2580(3) 0.60874(13) 0.0298(7) Uani 1 1 d . . . C33 C 0.16653(12) 0.4855(3) 0.44757(13) 0.0299(6) Uani 1 1 d . . . O1W O 0.28970(12) 0.7692(2) 0.44153(12) 0.0646(8) Uani 1 1 d . . . H1WA H 0.2613 0.7240 0.4445 0.078 Uiso 1 1 d R . . H1WB H 0.2991 0.8223 0.4717 0.078 Uiso 1 1 d 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 Mn1 0.0295(3) 0.0306(3) 0.0251(3) 0.00027(18) 0.0099(2) 0.00150(18) N1 0.0322(13) 0.0315(13) 0.0282(13) -0.0019(11) 0.0124(11) -0.0002(10) N2 0.0312(13) 0.0303(14) 0.0353(14) 0.0004(11) 0.0108(11) 0.0008(10) N3 0.0358(14) 0.0348(14) 0.0378(15) 0.0002(12) 0.0132(12) 0.0022(11) N4 0.0250(12) 0.0366(14) 0.0246(12) 0.0019(10) 0.0077(10) -0.0014(10) O1 0.052(2) 0.046(2) 0.057(2) 0.000 -0.0071(18) 0.000 O2 0.0388(13) 0.0640(16) 0.0595(16) -0.0289(14) 0.0130(12) 0.0060(12) O3 0.0241(10) 0.0465(12) 0.0256(11) -0.0029(9) 0.0022(9) -0.0023(9) O4 0.0475(12) 0.0354(11) 0.0249(11) -0.0010(9) 0.0098(10) 0.0004(9) O5 0.0627(15) 0.0368(13) 0.0446(13) 0.0028(11) 0.0143(12) -0.0132(11) C1 0.0390(17) 0.0382(18) 0.0371(17) 0.0000(14) 0.0174(14) 0.0018(14) C2 0.0403(18) 0.0324(17) 0.052(2) 0.0052(15) 0.0151(16) 0.0018(14) C3 0.0444(19) 0.0427(19) 0.0392(18) 0.0143(15) 0.0112(16) -0.0003(15) C4 0.0374(17) 0.0445(19) 0.0304(16) 0.0025(14) 0.0127(14) -0.0061(14) C5 0.068(2) 0.061(2) 0.0334(18) 0.0039(17) 0.0251(18) -0.0085(19) C6 0.067(2) 0.062(2) 0.0350(19) -0.0076(17) 0.0286(18) -0.0098(19) C7 0.0398(17) 0.0445(19) 0.0376(17) -0.0121(15) 0.0175(15) -0.0077(15) C8 0.063(2) 0.053(2) 0.049(2) -0.0199(18) 0.0298(19) -0.0025(18) C9 0.062(2) 0.0325(18) 0.069(3) -0.0107(18) 0.024(2) 0.0034(17) C10 0.049(2) 0.0364(19) 0.049(2) 0.0035(16) 0.0177(17) 0.0042(15) C11 0.0287(15) 0.0364(16) 0.0260(15) -0.0044(13) 0.0103(13) -0.0033(12) C12 0.0275(15) 0.0358(16) 0.0261(15) -0.0002(13) 0.0089(12) -0.0042(13) C13 0.0451(19) 0.046(2) 0.052(2) -0.0086(17) 0.0163(17) 0.0074(16) C14 0.0401(19) 0.058(2) 0.063(2) 0.000(2) 0.0226(18) 0.0130(17) C15 0.0282(16) 0.055(2) 0.057(2) 0.0064(18) 0.0129(16) 0.0038(15) C16 0.0278(15) 0.0461(19) 0.0390(18) 0.0043(15) 0.0093(14) -0.0013(14) C17 0.0309(17) 0.059(2) 0.055(2) -0.0042(19) 0.0071(16) -0.0109(16) C18 0.0408(19) 0.055(2) 0.049(2) -0.0180(18) 0.0097(17) -0.0164(17) C19 0.0356(16) 0.0398(17) 0.0328(16) -0.0042(14) 0.0105(14) -0.0086(14) C20 0.050(2) 0.0442(19) 0.0374(18) -0.0144(15) 0.0137(16) -0.0085(16) C21 0.0399(18) 0.0454(19) 0.0333(17) -0.0042(15) 0.0132(15) 0.0081(15) C22 0.0282(15) 0.0424(18) 0.0262(15) 0.0014(13) 0.0089(13) 0.0035(13) C23 0.0293(15) 0.0339(16) 0.0252(14) 0.0040(12) 0.0093(12) -0.0021(12) C24 0.0278(15) 0.0347(16) 0.0300(16) 0.0032(13) 0.0082(13) -0.0034(13) C25 0.029(2) 0.052(3) 0.037(3) 0.000 0.004(2) 0.000 C26 0.0329(16) 0.0451(18) 0.0289(16) 0.0006(14) 0.0009(14) 0.0023(14) C27 0.0305(17) 0.067(2) 0.047(2) -0.0107(18) -0.0015(16) 0.0149(16) C28 0.0399(19) 0.057(2) 0.0420(19) -0.0133(17) 0.0028(16) 0.0163(16) C29 0.0292(15) 0.0368(16) 0.0222(14) 0.0044(12) 0.0040(12) 0.0031(13) C30 0.0278(14) 0.0291(15) 0.0213(14) 0.0018(12) 0.0058(12) -0.0006(12) C31 0.0327(16) 0.0334(16) 0.0248(15) 0.0024(13) 0.0059(13) 0.0026(13) C32 0.0287(15) 0.0332(16) 0.0281(15) 0.0021(13) 0.0109(13) 0.0002(12) C33 0.0335(15) 0.0268(15) 0.0258(15) -0.0008(12) 0.0062(13) 0.0023(13) O1W 0.0687(18) 0.0642(17) 0.0695(18) -0.0262(14) 0.0349(16) -0.0078(14) _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 Mn1 O4 2.105(2) . y Mn1 O3 2.157(2) . y Mn1 N1 2.293(2) . y Mn1 N4 2.308(2) . y Mn1 N2 2.332(2) . y Mn1 N3 2.467(3) . y N1 C1 1.319(4) . ? N1 C12 1.355(4) . ? N2 C10 1.321(4) . ? N2 C11 1.363(4) . ? N3 C13 1.319(4) . ? N3 C24 1.359(4) . ? N4 C22 1.326(4) . ? N4 C23 1.363(3) . ? O1 C25 1.209(6) . ? O2 C32 1.230(3) . ? O3 C32 1.252(3) . ? O4 C33 1.276(3) . ? O5 C33 1.232(3) . ? C1 C2 1.389(4) . ? C1 H1 0.9300 . ? C2 C3 1.365(5) . ? C2 H2 0.9300 . ? C3 C4 1.407(5) . ? C3 H3 0.9300 . ? C4 C12 1.404(4) . ? C4 C5 1.426(5) . ? C5 C6 1.346(5) . ? C5 H5 0.9300 . ? C6 C7 1.439(5) . ? C6 H6 0.9300 . ? C7 C8 1.398(5) . ? C7 C11 1.398(4) . ? C8 C9 1.342(5) . ? C8 H8 0.9300 . ? C9 C10 1.408(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.453(4) . ? C13 C14 1.400(5) . ? C13 H13 0.9300 . ? C14 C15 1.362(5) . ? C14 H14 0.9300 . ? C15 C16 1.398(5) . ? C15 H15 0.9300 . ? C16 C24 1.417(4) . ? C16 C17 1.421(5) . ? C17 C18 1.332(5) . ? C17 H17 0.9300 . ? C18 C19 1.438(4) . ? C18 H18 0.9300 . ? C19 C23 1.399(4) . ? C19 C20 1.402(4) . ? C20 C21 1.356(4) . ? C20 H20 0.9300 . ? C21 C22 1.398(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.436(4) . ? C25 C26 1.503(4) . ? C25 C26 1.503(4) 2_656 ? C26 C31 1.377(4) . ? C26 C27 1.381(5) . ? C27 C28 1.384(4) . ? C27 H27 0.9300 . ? C28 C29 1.391(4) . ? C28 H28 0.9300 . ? C29 C30 1.402(4) . ? C29 C33 1.523(4) 7_556 ? C30 C31 1.388(4) . ? C30 C32 1.518(4) . ? C31 H31 0.9300 . ? C33 C29 1.523(4) 7_556 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? 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 Mn1 O3 100.81(8) . . y O4 Mn1 N1 164.98(8) . . y O3 Mn1 N1 82.32(8) . . y O4 Mn1 N4 106.38(8) . . y O3 Mn1 N4 84.98(8) . . y N1 Mn1 N4 88.48(8) . . y O4 Mn1 N2 94.37(8) . . y O3 Mn1 N2 119.78(8) . . y N1 Mn1 N2 71.63(8) . . y N4 Mn1 N2 144.33(8) . . y O4 Mn1 N3 91.79(8) . . y O3 Mn1 N3 153.73(8) . . y N1 Mn1 N3 91.46(8) . . y N4 Mn1 N3 69.30(8) . . y N2 Mn1 N3 81.61(8) . . y C1 N1 C12 117.9(3) . . ? C1 N1 Mn1 124.4(2) . . ? C12 N1 Mn1 117.43(19) . . ? C10 N2 C11 117.1(3) . . ? C10 N2 Mn1 126.9(2) . . ? C11 N2 Mn1 115.98(18) . . ? C13 N3 C24 117.1(3) . . ? C13 N3 Mn1 128.4(2) . . ? C24 N3 Mn1 114.51(18) . . ? C22 N4 C23 117.5(2) . . ? C22 N4 Mn1 122.56(18) . . ? C23 N4 Mn1 119.94(19) . . ? C32 O3 Mn1 107.24(18) . . ? C33 O4 Mn1 139.08(19) . . ? N1 C1 C2 123.3(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C12 C4 C3 117.8(3) . . ? C12 C4 C5 119.4(3) . . ? C3 C4 C5 122.8(3) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C11 116.7(3) . . ? C8 C7 C6 123.8(3) . . ? C11 C7 C6 119.5(3) . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? N2 C10 C9 122.7(3) . . ? N2 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N2 C11 C7 123.7(3) . . ? N2 C11 C12 117.3(2) . . ? C7 C11 C12 119.0(3) . . ? N1 C12 C4 122.5(3) . . ? N1 C12 C11 117.6(2) . . ? C4 C12 C11 119.8(3) . . ? N3 C13 C14 124.4(3) . . ? N3 C13 H13 117.8 . . ? C14 C13 H13 117.8 . . ? C15 C14 C13 118.6(3) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C24 117.5(3) . . ? C15 C16 C17 123.4(3) . . ? C24 C16 C17 119.1(3) . . ? C18 C17 C16 121.9(3) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 120.8(3) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C23 C19 C20 117.9(3) . . ? C23 C19 C18 119.5(3) . . ? C20 C19 C18 122.6(3) . . ? C21 C20 C19 119.8(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 118.8(3) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? N4 C22 C21 123.7(3) . . ? N4 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? N4 C23 C19 122.4(3) . . ? N4 C23 C24 118.1(3) . . ? C19 C23 C24 119.6(3) . . ? N3 C24 C16 122.6(3) . . ? N3 C24 C23 118.2(2) . . ? C16 C24 C23 119.2(3) . . ? O1 C25 C26 121.5(2) . . ? O1 C25 C26 121.5(2) . 2_656 ? C26 C25 C26 117.1(4) . 2_656 ? C31 C26 C27 119.1(3) . . ? C31 C26 C25 120.4(3) . . ? C27 C26 C25 120.5(3) . . ? C26 C27 C28 119.9(3) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C29 121.1(3) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C30 118.9(3) . . ? C28 C29 C33 116.0(3) . 7_556 ? C30 C29 C33 125.1(2) . 7_556 ? C31 C30 C29 118.8(3) . . ? C31 C30 C32 119.1(3) . . ? C29 C30 C32 122.2(2) . . ? C26 C31 C30 122.0(3) . . ? C26 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? O2 C32 O3 124.2(3) . . ? O2 C32 C30 118.3(3) . . ? O3 C32 C30 117.4(2) . . ? O5 C33 O4 125.0(3) . . ? O5 C33 C29 118.0(3) . 7_556 ? O4 C33 C29 116.6(2) . 7_556 ? H1WA O1W H1WB 104.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Mn1 N1 C1 -151.8(3) . . . . ? O3 Mn1 N1 C1 -48.6(2) . . . . ? N4 Mn1 N1 C1 36.5(2) . . . . ? N2 Mn1 N1 C1 -173.6(2) . . . . ? N3 Mn1 N1 C1 105.7(2) . . . . ? O4 Mn1 N1 C12 22.8(4) . . . . ? O3 Mn1 N1 C12 126.0(2) . . . . ? N4 Mn1 N1 C12 -148.9(2) . . . . ? N2 Mn1 N1 C12 1.04(19) . . . . ? N3 Mn1 N1 C12 -79.6(2) . . . . ? O4 Mn1 N2 C10 1.5(3) . . . . ? O3 Mn1 N2 C10 106.6(2) . . . . ? N1 Mn1 N2 C10 176.0(3) . . . . ? N4 Mn1 N2 C10 -124.8(2) . . . . ? N3 Mn1 N2 C10 -89.7(3) . . . . ? O4 Mn1 N2 C11 -176.61(19) . . . . ? O3 Mn1 N2 C11 -71.5(2) . . . . ? N1 Mn1 N2 C11 -2.14(19) . . . . ? N4 Mn1 N2 C11 57.1(2) . . . . ? N3 Mn1 N2 C11 92.2(2) . . . . ? O4 Mn1 N3 C13 -73.9(3) . . . . ? O3 Mn1 N3 C13 166.9(3) . . . . ? N1 Mn1 N3 C13 91.4(3) . . . . ? N4 Mn1 N3 C13 179.2(3) . . . . ? N2 Mn1 N3 C13 20.2(3) . . . . ? O4 Mn1 N3 C24 105.0(2) . . . . ? O3 Mn1 N3 C24 -14.2(3) . . . . ? N1 Mn1 N3 C24 -89.7(2) . . . . ? N4 Mn1 N3 C24 -1.89(19) . . . . ? N2 Mn1 N3 C24 -160.9(2) . . . . ? O4 Mn1 N4 C22 96.7(2) . . . . ? O3 Mn1 N4 C22 -3.2(2) . . . . ? N1 Mn1 N4 C22 -85.6(2) . . . . ? N2 Mn1 N4 C22 -140.3(2) . . . . ? N3 Mn1 N4 C22 -177.7(2) . . . . ? O4 Mn1 N4 C23 -83.7(2) . . . . ? O3 Mn1 N4 C23 176.5(2) . . . . ? N1 Mn1 N4 C23 94.1(2) . . . . ? N2 Mn1 N4 C23 39.4(3) . . . . ? N3 Mn1 N4 C23 1.94(19) . . . . ? O4 Mn1 O3 C32 86.87(19) . . . . ? N1 Mn1 O3 C32 -78.25(19) . . . . ? N4 Mn1 O3 C32 -167.38(19) . . . . ? N2 Mn1 O3 C32 -14.6(2) . . . . ? N3 Mn1 O3 C32 -155.8(2) . . . . ? O3 Mn1 O4 C33 68.8(3) . . . . ? N1 Mn1 O4 C33 169.6(3) . . . . ? N4 Mn1 O4 C33 -19.1(3) . . . . ? N2 Mn1 O4 C33 -169.7(3) . . . . ? N3 Mn1 O4 C33 -88.0(3) . . . . ? C12 N1 C1 C2 1.8(4) . . . . ? Mn1 N1 C1 C2 176.4(2) . . . . ? N1 C1 C2 C3 -0.7(5) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C12 -0.7(4) . . . . ? C2 C3 C4 C5 -178.4(3) . . . . ? C12 C4 C5 C6 -1.0(5) . . . . ? C3 C4 C5 C6 176.7(3) . . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C5 C6 C7 C8 -176.1(4) . . . . ? C5 C6 C7 C11 0.4(5) . . . . ? C11 C7 C8 C9 -1.6(5) . . . . ? C6 C7 C8 C9 175.1(3) . . . . ? C7 C8 C9 C10 0.7(6) . . . . ? C11 N2 C10 C9 -3.1(5) . . . . ? Mn1 N2 C10 C9 178.8(2) . . . . ? C8 C9 C10 N2 1.8(5) . . . . ? C10 N2 C11 C7 2.2(4) . . . . ? Mn1 N2 C11 C7 -179.5(2) . . . . ? C10 N2 C11 C12 -175.3(3) . . . . ? Mn1 N2 C11 C12 3.0(3) . . . . ? C8 C7 C11 N2 0.1(5) . . . . ? C6 C7 C11 N2 -176.7(3) . . . . ? C8 C7 C11 C12 177.6(3) . . . . ? C6 C7 C11 C12 0.8(4) . . . . ? C1 N1 C12 C4 -2.4(4) . . . . ? Mn1 N1 C12 C4 -177.4(2) . . . . ? C1 N1 C12 C11 175.1(2) . . . . ? Mn1 N1 C12 C11 0.1(3) . . . . ? C3 C4 C12 N1 1.9(4) . . . . ? C5 C4 C12 N1 179.7(3) . . . . ? C3 C4 C12 C11 -175.6(3) . . . . ? C5 C4 C12 C11 2.2(4) . . . . ? N2 C11 C12 N1 -2.1(4) . . . . ? C7 C11 C12 N1 -179.7(3) . . . . ? N2 C11 C12 C4 175.5(3) . . . . ? C7 C11 C12 C4 -2.1(4) . . . . ? C24 N3 C13 C14 0.2(5) . . . . ? Mn1 N3 C13 C14 179.1(3) . . . . ? N3 C13 C14 C15 0.1(6) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C24 0.6(5) . . . . ? C14 C15 C16 C17 -178.9(3) . . . . ? C15 C16 C17 C18 -178.9(4) . . . . ? C24 C16 C17 C18 1.6(5) . . . . ? C16 C17 C18 C19 -0.1(6) . . . . ? C17 C18 C19 C23 -1.3(5) . . . . ? C17 C18 C19 C20 177.6(3) . . . . ? C23 C19 C20 C21 -0.3(5) . . . . ? C18 C19 C20 C21 -179.2(3) . . . . ? C19 C20 C21 C22 -1.1(5) . . . . ? C23 N4 C22 C21 0.1(4) . . . . ? Mn1 N4 C22 C21 179.8(2) . . . . ? C20 C21 C22 N4 1.2(5) . . . . ? C22 N4 C23 C19 -1.6(4) . . . . ? Mn1 N4 C23 C19 178.8(2) . . . . ? C22 N4 C23 C24 177.8(3) . . . . ? Mn1 N4 C23 C24 -1.8(3) . . . . ? C20 C19 C23 N4 1.6(4) . . . . ? C18 C19 C23 N4 -179.4(3) . . . . ? C20 C19 C23 C24 -177.8(3) . . . . ? C18 C19 C23 C24 1.2(4) . . . . ? C13 N3 C24 C16 -0.2(4) . . . . ? Mn1 N3 C24 C16 -179.2(2) . . . . ? C13 N3 C24 C23 -179.3(3) . . . . ? Mn1 N3 C24 C23 1.7(3) . . . . ? C15 C16 C24 N3 -0.2(5) . . . . ? C17 C16 C24 N3 179.3(3) . . . . ? C15 C16 C24 C23 178.9(3) . . . . ? C17 C16 C24 C23 -1.6(4) . . . . ? N4 C23 C24 N3 -0.1(4) . . . . ? C19 C23 C24 N3 179.3(3) . . . . ? N4 C23 C24 C16 -179.2(3) . . . . ? C19 C23 C24 C16 0.2(4) . . . . ? O1 C25 C26 C31 -39.6(3) . . . . ? C26 C25 C26 C31 140.4(3) 2_656 . . . ? O1 C25 C26 C27 140.0(3) . . . . ? C26 C25 C26 C27 -40.0(3) 2_656 . . . ? C31 C26 C27 C28 2.5(5) . . . . ? C25 C26 C27 C28 -177.1(3) . . . . ? C26 C27 C28 C29 -1.8(6) . . . . ? C27 C28 C29 C30 -1.1(5) . . . . ? C27 C28 C29 C33 179.6(3) . . . 7_556 ? C28 C29 C30 C31 3.2(4) . . . . ? C33 C29 C30 C31 -177.6(3) 7_556 . . . ? C28 C29 C30 C32 -176.0(3) . . . . ? C33 C29 C30 C32 3.1(4) 7_556 . . . ? C27 C26 C31 C30 -0.4(5) . . . . ? C25 C26 C31 C30 179.2(3) . . . . ? C29 C30 C31 C26 -2.5(4) . . . . ? C32 C30 C31 C26 176.8(3) . . . . ? Mn1 O3 C32 O2 -6.9(4) . . . . ? Mn1 O3 C32 C30 173.16(19) . . . . ? C31 C30 C32 O2 -7.6(4) . . . . ? C29 C30 C32 O2 171.7(3) . . . . ? C31 C30 C32 O3 172.4(3) . . . . ? C29 C30 C32 O3 -8.3(4) . . . . ? Mn1 O4 C33 O5 -146.4(2) . . . . ? Mn1 O4 C33 C29 40.6(4) . . . 7_556 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O5 0.85 2.18 3.020(3) 167.9 . O1W H1WB O5 0.85 2.29 3.111(3) 161.9 7_566 O1W H1WB O4 0.85 2.39 3.102(3) 141.0 7_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.627 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 857478' ####################################################################### # # 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_3473-sr #TrackingRef '3473-sr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H15 N2 O10 Zn2' _chemical_formula_sum 'C27 H15 N2 O10 Zn2' _chemical_formula_weight 658.15 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_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0612(16) _cell_length_b 15.0262(17) _cell_length_c 16.7833(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.4910(10) _cell_angle_gamma 90.00 _cell_volume 2776.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1112 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 17.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1324 _exptl_absorpt_coefficient_mu 1.787 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5207 _exptl_absorpt_correction_T_max 0.6346 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13898 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4884 _reflns_number_gt 4043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2009)' _computing_cell_refinement 'APEX 2' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2009)' _computing_publication_material 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^)+(0.0468P)^2^+1.0093P] 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 4884 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.4514(2) -0.03049(14) 0.30477(13) 0.0310(5) Uani 1 1 d . . . C27 C 0.5682(3) -0.0234(2) 0.2931(2) 0.0441(8) Uani 1 1 d . . . H27 H 0.6227 -0.0644 0.3176 0.053 Uiso 1 1 calc R . . O4 O 1.25950(18) 0.50863(12) -0.03383(11) 0.0350(5) Uani 1 1 d . . . C8 C 1.2265(2) 0.43932(17) -0.00174(16) 0.0273(6) Uani 1 1 d . . . Zn1 Zn 0.72073(3) 0.383712(19) -0.034358(18) 0.02593(10) Uani 1 1 d . . . Zn2 Zn 1.11418(3) 0.36344(2) 0.135395(19) 0.03164(11) Uani 1 1 d . . . O6 O 0.58570(17) 0.40630(13) -0.11611(12) 0.0361(5) Uani 1 1 d . . . O2 O 0.98251(19) 0.38272(15) 0.03914(12) 0.0470(6) Uani 1 1 d . . . N1 N 0.6583(2) 0.29433(14) 0.04353(14) 0.0302(5) Uani 1 1 d . . . O5 O 1.2022(2) 0.14052(13) -0.27782(13) 0.0450(5) Uani 1 1 d . . . O3 O 1.2274(2) 0.43080(14) 0.07266(12) 0.0443(5) Uani 1 1 d . . . O11 O 1.25938(19) 0.33253(14) 0.22874(13) 0.0447(5) Uani 1 1 d . . . H11 H 1.2468 0.2837 0.2481 0.067 Uiso 1 1 calc R . . O1 O 0.87289(17) 0.33856(13) -0.06936(12) 0.0369(5) Uani 1 1 d . . . C1 C 0.9728(2) 0.34954(17) -0.02838(16) 0.0269(6) Uani 1 1 d . . . C14 C 0.6008(2) 0.37952(17) -0.18651(18) 0.0304(6) Uani 1 1 d . . . C25 C 0.5341(3) 0.10421(17) 0.20813(16) 0.0298(6) Uani 1 1 d . . . C2 C 1.0838(2) 0.31859(16) -0.06684(15) 0.0236(5) Uani 1 1 d . . . C7 C 1.1959(2) 0.36192(16) -0.05696(16) 0.0266(6) Uani 1 1 d . . . C4 C 1.1650(3) 0.21564(17) -0.15979(16) 0.0299(6) Uani 1 1 d . . . C11 C 0.4179(3) 0.55844(17) -0.30329(17) 0.0303(6) Uani 1 1 d . . . O7 O 0.6744(2) 0.32212(14) -0.20196(13) 0.0453(5) Uani 1 1 d . . . C20 C 0.5770(3) 0.17162(17) 0.15218(17) 0.0301(6) Uani 1 1 d . . . C21 C 0.6950(3) 0.1711(2) 0.1315(2) 0.0429(8) Uani 1 1 d . . . H21 H 0.7499 0.1290 0.1537 0.051 Uiso 1 1 calc R . . C5 C 1.2737(3) 0.26286(18) -0.15297(18) 0.0344(7) Uani 1 1 d . . . H5 H 1.3364 0.2458 -0.1828 0.041 Uiso 1 1 calc R . . O8 O 1.0125(2) 0.26172(14) 0.17523(17) 0.0633(8) Uani 1 1 d . . . C15 C 0.5224(3) 0.39476(17) -0.33255(18) 0.0319(6) Uani 1 1 d . . . C6 C 1.2886(2) 0.33490(18) -0.10198(17) 0.0317(6) Uani 1 1 d . . . H6 H 1.3618 0.3659 -0.0976 0.038 Uiso 1 1 calc R . . C3 C 1.0697(2) 0.24521(17) -0.11820(16) 0.0292(6) Uani 1 1 d . . . H3 H 0.9955 0.2157 -0.1246 0.035 Uiso 1 1 calc R . . C10 C 0.4199(3) 0.52823(18) -0.38083(17) 0.0351(7) Uani 1 1 d . . . H10 H 0.3886 0.5635 -0.4234 0.042 Uiso 1 1 calc R . . C23 C 0.3774(3) 0.0321(2) 0.2715(2) 0.0442(8) Uani 1 1 d . . . H23 H 0.2960 0.0302 0.2812 0.053 Uiso 1 1 calc R . . C13 C 0.5272(3) 0.42695(17) -0.25427(17) 0.0302(6) Uani 1 1 d . . . C12 C 0.4733(3) 0.50717(18) -0.24000(17) 0.0326(6) Uani 1 1 d . . . H12 H 0.4736 0.5277 -0.1877 0.039 Uiso 1 1 calc R . . C9 C 1.1520(3) 0.13944(17) -0.21654(17) 0.0318(6) Uani 1 1 d . . . C19 C 0.5012(3) 0.2366(2) 0.11712(19) 0.0422(8) Uani 1 1 d . . . H19 H 0.4211 0.2404 0.1293 0.051 Uiso 1 1 calc R . . C24 C 0.4144(3) 0.0992(2) 0.2238(2) 0.0462(8) Uani 1 1 d . . . H24 H 0.3587 0.1411 0.2022 0.055 Uiso 1 1 calc R . . C26 C 0.6116(3) 0.0421(2) 0.24633(19) 0.0455(8) Uani 1 1 d . . . H26 H 0.6943 0.0448 0.2403 0.055 Uiso 1 1 calc R . . C16 C 0.4681(3) 0.44593(19) -0.39529(18) 0.0363(7) Uani 1 1 d . . . H16 H 0.4644 0.4244 -0.4474 0.044 Uiso 1 1 calc R . . C22 C 0.7315(3) 0.2330(2) 0.0782(2) 0.0418(8) Uani 1 1 d . . . H22 H 0.8117 0.2316 0.0659 0.050 Uiso 1 1 calc R . . C18 C 0.5445(3) 0.2958(2) 0.06408(19) 0.0402(7) Uani 1 1 d . . . H18 H 0.4919 0.3391 0.0414 0.048 Uiso 1 1 calc R . . C17 C 1.0688(3) 0.1963(2) 0.1477(2) 0.0476(9) Uani 1 1 d . . . O9 O 1.1523(3) 0.20431(18) 0.10569(16) 0.0713(8) 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 N2 0.0376(14) 0.0278(12) 0.0286(12) 0.0007(10) 0.0081(10) 0.0010(10) C27 0.0391(18) 0.0437(18) 0.0492(19) 0.0203(16) 0.0031(15) 0.0050(14) O4 0.0478(12) 0.0243(10) 0.0333(11) -0.0034(8) 0.0057(9) -0.0093(9) C8 0.0264(14) 0.0276(14) 0.0287(15) -0.0033(12) 0.0072(12) -0.0034(11) Zn1 0.02806(18) 0.02406(17) 0.02587(18) 0.00044(13) 0.00361(13) -0.00296(12) Zn2 0.0375(2) 0.02990(18) 0.02823(19) -0.00467(14) 0.00668(14) -0.00232(14) O6 0.0333(11) 0.0416(11) 0.0325(11) 0.0035(9) -0.0022(9) -0.0009(9) O2 0.0391(12) 0.0704(15) 0.0306(12) -0.0193(11) -0.0008(10) 0.0153(11) N1 0.0342(13) 0.0262(12) 0.0304(12) 0.0025(10) 0.0045(10) -0.0013(10) O5 0.0612(15) 0.0364(12) 0.0399(13) -0.0068(10) 0.0177(11) -0.0031(10) O3 0.0603(14) 0.0436(12) 0.0299(11) -0.0065(10) 0.0099(10) -0.0266(10) O11 0.0403(12) 0.0457(13) 0.0479(13) 0.0018(11) 0.0023(10) -0.0023(10) O1 0.0260(11) 0.0466(12) 0.0379(11) -0.0148(10) 0.0027(9) -0.0014(9) C1 0.0327(15) 0.0214(13) 0.0269(15) 0.0009(11) 0.0044(12) -0.0011(11) C14 0.0279(15) 0.0252(14) 0.0373(17) 0.0031(12) -0.0012(13) -0.0076(11) C25 0.0352(16) 0.0251(14) 0.0294(15) 0.0004(12) 0.0044(12) -0.0020(11) C2 0.0287(14) 0.0202(12) 0.0225(13) -0.0003(10) 0.0047(11) -0.0004(10) C7 0.0319(15) 0.0215(13) 0.0265(14) -0.0012(11) 0.0039(12) -0.0011(11) C4 0.0353(15) 0.0227(14) 0.0320(15) -0.0033(11) 0.0039(13) 0.0012(11) C11 0.0341(15) 0.0217(13) 0.0354(16) 0.0076(12) 0.0049(13) -0.0010(11) O7 0.0463(13) 0.0431(12) 0.0441(13) -0.0018(10) -0.0073(10) 0.0149(10) C20 0.0356(16) 0.0269(14) 0.0287(15) 0.0031(12) 0.0068(12) -0.0006(12) C21 0.0391(17) 0.0360(17) 0.055(2) 0.0180(15) 0.0127(15) 0.0104(13) C5 0.0307(15) 0.0326(15) 0.0413(17) -0.0034(13) 0.0104(13) 0.0021(12) O8 0.0575(15) 0.0229(11) 0.103(2) 0.0010(13) -0.0272(15) -0.0008(10) C15 0.0319(15) 0.0236(14) 0.0391(16) 0.0005(12) -0.0022(13) -0.0046(11) C6 0.0285(15) 0.0299(14) 0.0371(16) -0.0064(13) 0.0056(13) -0.0071(11) C3 0.0272(14) 0.0256(14) 0.0352(16) -0.0046(12) 0.0045(12) -0.0044(11) C10 0.0425(17) 0.0293(15) 0.0323(16) 0.0077(13) -0.0033(13) 0.0027(12) C23 0.0385(17) 0.0379(17) 0.060(2) 0.0191(16) 0.0241(16) 0.0125(14) C13 0.0337(15) 0.0227(14) 0.0337(15) 0.0058(12) 0.0012(12) -0.0053(11) C12 0.0381(16) 0.0281(14) 0.0314(15) 0.0010(12) 0.0026(13) -0.0016(12) C9 0.0374(16) 0.0265(14) 0.0319(16) -0.0008(12) 0.0049(13) 0.0033(12) C19 0.0337(16) 0.0463(18) 0.0480(19) 0.0156(15) 0.0105(14) 0.0032(14) C24 0.0431(18) 0.0338(16) 0.065(2) 0.0214(16) 0.0232(17) 0.0129(14) C26 0.0307(16) 0.056(2) 0.050(2) 0.0225(16) 0.0034(15) 0.0003(14) C16 0.0461(18) 0.0323(15) 0.0297(15) -0.0019(12) -0.0006(13) -0.0023(13) C22 0.0314(16) 0.0430(17) 0.053(2) 0.0130(15) 0.0148(15) 0.0032(13) C18 0.0314(16) 0.0433(18) 0.0456(18) 0.0173(15) 0.0032(14) 0.0049(13) C17 0.056(2) 0.0355(18) 0.046(2) 0.0105(15) -0.0209(17) -0.0084(16) O9 0.090(2) 0.0667(18) 0.0581(17) 0.0163(14) 0.0116(16) -0.0314(15) _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 N2 C27 1.329(4) . ? N2 C23 1.334(4) . ? N2 Zn2 2.053(2) 2_645 y C27 C26 1.374(4) . ? C27 H27 0.9300 . ? O4 C8 1.243(3) . ? O4 Zn1 1.9816(18) 3_765 y C8 O3 1.254(3) . ? C8 C7 1.505(4) . ? Zn1 O1 1.9563(19) . y Zn1 O6 1.9587(19) . y Zn1 O4 1.9816(18) 3_765 y Zn1 N1 2.040(2) . y Zn2 O3 1.989(2) . y Zn2 O8 2.048(2) . y Zn2 N2 2.053(2) 2_655 y Zn2 O2 2.089(2) . y Zn2 O11 2.184(2) . y Zn2 O9 2.487(3) . y O6 C14 1.274(3) . ? O2 C1 1.233(3) . ? N1 C22 1.324(4) . ? N1 C18 1.337(4) . ? O5 C9 1.214(3) . ? O11 H11 0.8200 . ? O1 C1 1.256(3) . ? C1 C2 1.513(4) . ? C14 O7 1.230(3) . ? C14 C13 1.512(4) . ? C25 C24 1.377(4) . ? C25 C26 1.382(4) . ? C25 C20 1.489(4) . ? C2 C7 1.397(4) . ? C2 C3 1.399(4) . ? C7 C6 1.392(4) . ? C4 C3 1.391(4) . ? C4 C5 1.392(4) . ? C4 C9 1.487(4) . ? C11 C10 1.380(4) . ? C11 C12 1.405(4) . ? C11 C9 1.496(4) 2_654 ? C20 C19 1.382(4) . ? C20 C21 1.382(4) . ? C21 C22 1.378(4) . ? C21 H21 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? O8 C17 1.274(4) . ? C15 C16 1.393(4) . ? C15 C13 1.396(4) . ? C15 C17 1.509(4) 4_565 ? C6 H6 0.9300 . ? C3 H3 0.9300 . ? C10 C16 1.378(4) . ? C10 H10 0.9300 . ? C23 C24 1.374(4) . ? C23 H23 0.9300 . ? C13 C12 1.376(4) . ? C12 H12 0.9300 . ? C9 C11 1.496(4) 2_644 ? C19 C18 1.377(4) . ? C19 H19 0.9300 . ? C24 H24 0.9300 . ? C26 H26 0.9300 . ? C16 H16 0.9300 . ? C22 H22 0.9300 . ? C18 H18 0.9300 . ? C17 O9 1.221(4) . ? C17 C15 1.509(4) 4_666 ? 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 C27 N2 C23 116.6(2) . . ? C27 N2 Zn2 121.91(19) . 2_645 ? C23 N2 Zn2 121.4(2) . 2_645 ? N2 C27 C26 122.7(3) . . ? N2 C27 H27 118.7 . . ? C26 C27 H27 118.7 . . ? C8 O4 Zn1 117.03(17) . 3_765 ? O4 C8 O3 122.8(2) . . ? O4 C8 C7 116.0(2) . . ? O3 C8 C7 120.9(2) . . ? O1 Zn1 O6 118.03(8) . . y O1 Zn1 O4 113.95(8) . 3_765 y O6 Zn1 O4 107.32(8) . 3_765 y O1 Zn1 N1 108.52(9) . . y O6 Zn1 N1 106.31(9) . . y O4 Zn1 N1 101.12(8) 3_765 . y O3 Zn2 O8 161.16(10) . . y O3 Zn2 N2 97.70(9) . 2_655 y O8 Zn2 N2 100.88(10) . 2_655 y O3 Zn2 O2 87.01(9) . . y O8 Zn2 O2 89.53(10) . . y N2 Zn2 O2 91.02(9) 2_655 . y O3 Zn2 O11 91.76(9) . . y O8 Zn2 O11 89.79(9) . . y N2 Zn2 O11 94.84(9) 2_655 . y O2 Zn2 O11 174.13(8) . . y O3 Zn2 O9 104.82(9) . . y O8 Zn2 O9 57.09(10) . . y N2 Zn2 O9 156.80(9) 2_655 . y O2 Zn2 O9 95.58(9) . . y O11 Zn2 O9 79.18(9) . . y C14 O6 Zn1 115.83(18) . . ? C1 O2 Zn2 130.33(19) . . ? C22 N1 C18 116.7(2) . . ? C22 N1 Zn1 120.64(19) . . ? C18 N1 Zn1 122.61(19) . . ? C8 O3 Zn2 129.29(18) . . ? Zn2 O11 H11 109.5 . . ? C1 O1 Zn1 121.84(17) . . ? O2 C1 O1 123.4(3) . . ? O2 C1 C2 120.9(2) . . ? O1 C1 C2 115.7(2) . . ? O7 C14 O6 124.4(3) . . ? O7 C14 C13 119.4(3) . . ? O6 C14 C13 116.1(2) . . ? C24 C25 C26 116.1(3) . . ? C24 C25 C20 121.9(3) . . ? C26 C25 C20 122.0(3) . . ? C7 C2 C3 119.0(2) . . ? C7 C2 C1 123.6(2) . . ? C3 C2 C1 117.3(2) . . ? C6 C7 C2 119.5(2) . . ? C6 C7 C8 115.2(2) . . ? C2 C7 C8 125.3(2) . . ? C3 C4 C5 119.1(2) . . ? C3 C4 C9 122.4(2) . . ? C5 C4 C9 118.3(2) . . ? C10 C11 C12 119.2(3) . . ? C10 C11 C9 122.2(2) . 2_654 ? C12 C11 C9 118.4(3) . 2_654 ? C19 C20 C21 116.5(3) . . ? C19 C20 C25 122.1(3) . . ? C21 C20 C25 121.3(3) . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C17 O8 Zn2 98.9(2) . . ? C16 C15 C13 119.7(3) . . ? C16 C15 C17 117.8(3) . 4_565 ? C13 C15 C17 122.5(3) . 4_565 ? C5 C6 C7 121.0(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C16 C10 C11 120.2(3) . . ? C16 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? N2 C23 C24 123.8(3) . . ? N2 C23 H23 118.1 . . ? C24 C23 H23 118.1 . . ? C12 C13 C15 119.3(3) . . ? C12 C13 C14 119.5(3) . . ? C15 C13 C14 120.9(2) . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? O5 C9 C4 120.6(3) . . ? O5 C9 C11 119.1(2) . 2_644 ? C4 C9 C11 120.2(2) . 2_644 ? C18 C19 C20 119.8(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C23 C24 C25 119.8(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C27 C26 C25 120.9(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C10 C16 C15 120.6(3) . . ? C10 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? N1 C22 C21 123.4(3) . . ? N1 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? N1 C18 C19 123.4(3) . . ? N1 C18 H18 118.3 . . ? C19 C18 H18 118.3 . . ? O9 C17 O8 123.8(3) . . ? O9 C17 C15 120.6(3) . 4_666 ? O8 C17 C15 115.6(3) . 4_666 ? C17 O9 Zn2 80.0(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 C23 N2 C27 C26 -3.0(5) . . . . ? Zn2 N2 C27 C26 173.2(3) 2_645 . . . ? Zn1 O4 C8 O3 -13.5(4) 3_765 . . . ? Zn1 O4 C8 C7 172.08(17) 3_765 . . . ? O1 Zn1 O6 C14 8.4(2) . . . . ? O4 Zn1 O6 C14 138.80(18) 3_765 . . . ? N1 Zn1 O6 C14 -113.64(19) . . . . ? O3 Zn2 O2 C1 71.4(3) . . . . ? O8 Zn2 O2 C1 -90.1(3) . . . . ? N2 Zn2 O2 C1 169.0(3) 2_655 . . . ? O9 Zn2 O2 C1 -33.2(3) . . . . ? O1 Zn1 N1 C22 17.3(3) . . . . ? O6 Zn1 N1 C22 145.3(2) . . . . ? O4 Zn1 N1 C22 -102.8(2) 3_765 . . . ? O1 Zn1 N1 C18 -164.7(2) . . . . ? O6 Zn1 N1 C18 -36.8(3) . . . . ? O4 Zn1 N1 C18 75.1(2) 3_765 . . . ? O4 C8 O3 Zn2 145.9(2) . . . . ? C7 C8 O3 Zn2 -40.0(4) . . . . ? O8 Zn2 O3 C8 52.9(5) . . . . ? N2 Zn2 O3 C8 -117.4(3) 2_655 . . . ? O2 Zn2 O3 C8 -26.8(3) . . . . ? O11 Zn2 O3 C8 147.5(3) . . . . ? O9 Zn2 O3 C8 68.2(3) . . . . ? O6 Zn1 O1 C1 156.1(2) . . . . ? O4 Zn1 O1 C1 28.8(2) 3_765 . . . ? N1 Zn1 O1 C1 -83.0(2) . . . . ? Zn2 O2 C1 O1 151.8(2) . . . . ? Zn2 O2 C1 C2 -27.7(4) . . . . ? Zn1 O1 C1 O2 6.0(4) . . . . ? Zn1 O1 C1 C2 -174.45(16) . . . . ? Zn1 O6 C14 O7 20.6(4) . . . . ? Zn1 O6 C14 C13 -155.66(17) . . . . ? O2 C1 C2 C7 -35.8(4) . . . . ? O1 C1 C2 C7 144.6(3) . . . . ? O2 C1 C2 C3 147.6(3) . . . . ? O1 C1 C2 C3 -32.0(3) . . . . ? C3 C2 C7 C6 4.0(4) . . . . ? C1 C2 C7 C6 -172.5(2) . . . . ? C3 C2 C7 C8 -177.6(2) . . . . ? C1 C2 C7 C8 5.9(4) . . . . ? O4 C8 C7 C6 57.2(3) . . . . ? O3 C8 C7 C6 -117.3(3) . . . . ? O4 C8 C7 C2 -121.2(3) . . . . ? O3 C8 C7 C2 64.3(4) . . . . ? C24 C25 C20 C19 4.5(5) . . . . ? C26 C25 C20 C19 -176.6(3) . . . . ? C24 C25 C20 C21 -174.3(3) . . . . ? C26 C25 C20 C21 4.6(4) . . . . ? C19 C20 C21 C22 -0.4(5) . . . . ? C25 C20 C21 C22 178.5(3) . . . . ? C3 C4 C5 C6 3.7(4) . . . . ? C9 C4 C5 C6 178.9(3) . . . . ? O3 Zn2 O8 C17 19.9(4) . . . . ? N2 Zn2 O8 C17 -169.9(2) 2_655 . . . ? O2 Zn2 O8 C17 99.2(2) . . . . ? O11 Zn2 O8 C17 -75.0(2) . . . . ? O9 Zn2 O8 C17 2.20(19) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C2 C7 C6 C5 -3.6(4) . . . . ? C8 C7 C6 C5 177.9(3) . . . . ? C5 C4 C3 C2 -3.3(4) . . . . ? C9 C4 C3 C2 -178.3(2) . . . . ? C7 C2 C3 C4 -0.6(4) . . . . ? C1 C2 C3 C4 176.1(2) . . . . ? C12 C11 C10 C16 4.6(4) . . . . ? C9 C11 C10 C16 -169.2(3) 2_654 . . . ? C27 N2 C23 C24 3.2(5) . . . . ? Zn2 N2 C23 C24 -172.9(3) 2_645 . . . ? C16 C15 C13 C12 2.9(4) . . . . ? C17 C15 C13 C12 -174.1(3) 4_565 . . . ? C16 C15 C13 C14 -171.1(2) . . . . ? C17 C15 C13 C14 11.8(4) 4_565 . . . ? O7 C14 C13 C12 -160.7(3) . . . . ? O6 C14 C13 C12 15.7(4) . . . . ? O7 C14 C13 C15 13.3(4) . . . . ? O6 C14 C13 C15 -170.3(2) . . . . ? C15 C13 C12 C11 -2.5(4) . . . . ? C14 C13 C12 C11 171.6(2) . . . . ? C10 C11 C12 C13 -1.2(4) . . . . ? C9 C11 C12 C13 172.8(3) 2_654 . . . ? C3 C4 C9 O5 142.6(3) . . . . ? C5 C4 C9 O5 -32.5(4) . . . . ? C3 C4 C9 C11 -40.6(4) . . . 2_644 ? C5 C4 C9 C11 144.4(3) . . . 2_644 ? C21 C20 C19 C18 0.7(5) . . . . ? C25 C20 C19 C18 -178.2(3) . . . . ? N2 C23 C24 C25 0.0(5) . . . . ? C26 C25 C24 C23 -3.5(5) . . . . ? C20 C25 C24 C23 175.5(3) . . . . ? N2 C27 C26 C25 -0.6(5) . . . . ? C24 C25 C26 C27 3.8(5) . . . . ? C20 C25 C26 C27 -175.2(3) . . . . ? C11 C10 C16 C15 -4.2(4) . . . . ? C13 C15 C16 C10 0.4(4) . . . . ? C17 C15 C16 C10 177.6(3) 4_565 . . . ? C18 N1 C22 C21 1.6(5) . . . . ? Zn1 N1 C22 C21 179.7(3) . . . . ? C20 C21 C22 N1 -0.8(5) . . . . ? C22 N1 C18 C19 -1.3(5) . . . . ? Zn1 N1 C18 C19 -179.3(2) . . . . ? C20 C19 C18 N1 0.2(5) . . . . ? Zn2 O8 C17 O9 -4.5(4) . . . . ? Zn2 O8 C17 C15 178.0(2) . . . 4_666 ? O8 C17 O9 Zn2 3.8(3) . . . . ? C15 C17 O9 Zn2 -178.9(3) 4_666 . . . ? O3 Zn2 O9 C17 -176.5(2) . . . . ? O8 Zn2 O9 C17 -2.31(19) . . . . ? N2 Zn2 O9 C17 17.7(4) 2_655 . . . ? O2 Zn2 O9 C17 -88.1(2) . . . . ? O11 Zn2 O9 C17 94.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.677 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 863678' ####################################################################### # # 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_3677 #TrackingRef '3677.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H16 N2 O10 Zn2, 0.5(C10 H8 N2)' _chemical_formula_sum 'C32 H20 N3 O10 Zn2' _chemical_formula_weight 737.25 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_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0632(6) _cell_length_b 15.0159(8) _cell_length_c 16.7772(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.3940(10) _cell_angle_gamma 90.00 _cell_volume 2774.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1759 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 20.38 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1492 _exptl_absorpt_coefficient_mu 1.800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5257 _exptl_absorpt_correction_T_max 0.6519 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13891 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4873 _reflns_number_gt 4232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2009)' _computing_cell_refinement 'APEX 2' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2009)' _computing_publication_material 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^)+(0.0472P)^2^+2.3010P] 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 4873 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.21938(3) 0.11652(2) -0.033322(18) 0.02263(10) Uani 1 1 d . . . Zn2 Zn 0.61296(3) 0.13881(2) 0.134581(19) 0.03022(11) Uani 1 1 d . . . C1 C 0.3995(2) 0.62129(18) -0.31447(17) 0.0265(6) Uani 1 1 d . . . C2 C 0.4734(3) 0.57399(18) -0.24623(17) 0.0261(6) Uani 1 1 d . . . C3 C 0.5263(3) 0.49268(18) -0.26004(16) 0.0282(6) Uani 1 1 d . . . H3 H 0.5254 0.4714 -0.3122 0.034 Uiso 1 1 calc R . . C4 C 0.5809(3) 0.44214(18) -0.19682(17) 0.0277(6) Uani 1 1 d . . . C5 C 0.5802(3) 0.47280(19) -0.11896(17) 0.0306(6) Uani 1 1 d . . . H5 H 0.6119 0.4379 -0.0763 0.037 Uiso 1 1 calc R . . C6 C 0.5316(3) 0.55608(19) -0.10514(18) 0.0318(7) Uani 1 1 d . . . H6 H 0.5344 0.5778 -0.0531 0.038 Uiso 1 1 calc R . . C7 C 0.4792(3) 0.60715(18) -0.16793(17) 0.0277(6) Uani 1 1 d . . . C8 C 0.4382(3) 0.7005(2) -0.15070(19) 0.0361(7) Uani 1 1 d . . . C9 C 0.6505(3) 0.36081(18) -0.21652(17) 0.0284(6) Uani 1 1 d . . . C10 C 0.4716(3) 0.15184(17) -0.02695(16) 0.0247(6) Uani 1 1 d . . . C11 C 0.5824(2) 0.18194(17) -0.06552(15) 0.0219(5) Uani 1 1 d . . . C12 C 0.5691(3) 0.25527(18) -0.11700(16) 0.0258(6) Uani 1 1 d . . . H12 H 0.4953 0.2854 -0.1229 0.031 Uiso 1 1 calc R . . C13 C 0.6637(3) 0.28402(17) -0.15939(16) 0.0266(6) Uani 1 1 d . . . C14 C 0.7721(3) 0.23661(19) -0.15330(17) 0.0295(6) Uani 1 1 d . . . H14 H 0.8344 0.2534 -0.1837 0.035 Uiso 1 1 calc R . . C15 C 0.7872(3) 0.16445(19) -0.10198(17) 0.0292(6) Uani 1 1 d . . . H15 H 0.8601 0.1332 -0.0979 0.035 Uiso 1 1 calc R . . C16 C 0.6947(2) 0.13822(17) -0.05642(16) 0.0239(6) Uani 1 1 d . . . C17 C 0.7255(2) 0.05994(18) -0.00129(16) 0.0244(6) Uani 1 1 d . . . C18 C 0.4328(3) 0.0253(2) 0.20610(19) 0.0391(8) Uani 1 1 d . . . H18 H 0.3785 0.0665 0.1818 0.047 Uiso 1 1 calc R . . C19 C 0.3896(3) -0.0397(2) 0.2535(2) 0.0418(8) Uani 1 1 d . . . H19 H 0.3073 -0.0413 0.2609 0.050 Uiso 1 1 calc R . . C20 C 0.6228(3) -0.0316(2) 0.2250(2) 0.0417(8) Uani 1 1 d . . . H20 H 0.7035 -0.0306 0.2138 0.050 Uiso 1 1 calc R . . C21 C 0.5864(3) -0.0983(2) 0.2734(2) 0.0433(8) Uani 1 1 d . . . H21 H 0.6422 -0.1403 0.2946 0.052 Uiso 1 1 calc R . . C22 C 0.4669(3) -0.10292(18) 0.29054(17) 0.0270(6) Uani 1 1 d . . . C23 C 0.4246(3) -0.17018(18) 0.34688(17) 0.0271(6) Uani 1 1 d . . . C24 C 0.5007(3) -0.2356(2) 0.3822(2) 0.0392(8) Uani 1 1 d . . . H24 H 0.5808 -0.2394 0.3700 0.047 Uiso 1 1 calc R . . C25 C 0.4573(3) -0.2949(2) 0.4353(2) 0.0379(7) Uani 1 1 d . . . H25 H 0.5099 -0.3384 0.4579 0.045 Uiso 1 1 calc R . . C26 C 0.3066(3) -0.1699(2) 0.3678(2) 0.0396(8) Uani 1 1 d . . . H26 H 0.2518 -0.1277 0.3457 0.048 Uiso 1 1 calc R . . C27 C 0.2702(3) -0.2315(2) 0.4210(2) 0.0383(7) Uani 1 1 d . . . H27 H 0.1899 -0.2302 0.4332 0.046 Uiso 1 1 calc R . . C28 C 0.1027(5) 0.3682(3) 0.8847(3) 0.0730(13) Uani 1 1 d . . . H28 H 0.0823 0.3161 0.8566 0.088 Uiso 1 1 calc R . . C29 C 0.0189(5) 0.4033(3) 0.9322(3) 0.0703(13) Uani 1 1 d . . . H29 H -0.0552 0.3749 0.9350 0.084 Uiso 1 1 calc R . . C30 C 0.0443(3) 0.4797(2) 0.97490(19) 0.0448(8) Uani 1 1 d . . . C31 C 0.1556(4) 0.5183(3) 0.9672(3) 0.0714(13) Uani 1 1 d . . . H31 H 0.1776 0.5707 0.9944 0.086 Uiso 1 1 calc R . . C32 C 0.2340(4) 0.4788(4) 0.9189(3) 0.0808(15) Uani 1 1 d . . . H32 H 0.3088 0.5060 0.9152 0.097 Uiso 1 1 calc R . . N1 N 0.5495(2) 0.03141(15) 0.19357(13) 0.0273(5) Uani 1 1 d . . . N2 N 0.3439(2) -0.29323(15) 0.45600(14) 0.0273(5) Uani 1 1 d . . . N3 N 0.2106(4) 0.4041(3) 0.8768(2) 0.0674(10) Uani 1 1 d . . . O1 O 0.41504(18) 0.59468(14) -0.38461(12) 0.0320(5) Uani 1 1 d . . . O2 O 0.3250(2) 0.67813(14) -0.29860(13) 0.0390(5) Uani 1 1 d . . . O3 O 0.4927(2) 0.76355(14) -0.18211(15) 0.0442(6) Uani 1 1 d . . . O4 O 0.3579(2) 0.71243(17) -0.10549(14) 0.0524(6) Uani 1 1 d . . . O5 O 0.7006(2) 0.35943(14) -0.27748(13) 0.0409(5) Uani 1 1 d . . . O6 O 0.37195(17) 0.16136(14) -0.06834(12) 0.0329(5) Uani 1 1 d . . . O7 O 0.47999(19) 0.12133(15) 0.04222(12) 0.0404(5) Uani 1 1 d . . . O8 O 0.7231(2) 0.06669(14) 0.07249(12) 0.0401(5) Uani 1 1 d . . . O9 O 0.76117(19) -0.00877(13) -0.03455(11) 0.0307(4) Uani 1 1 d . . . O1W O 0.75580(19) 0.16798(15) 0.22614(13) 0.0380(5) Uani 1 1 d . . . H1WA H 0.7454 0.2206 0.2429 0.046 Uiso 1 1 d R . . H1WB H 0.7660 0.1340 0.2668 0.046 Uiso 1 1 d 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 0.02322(18) 0.02089(17) 0.02380(17) -0.00051(12) 0.00241(13) 0.00229(12) Zn2 0.0336(2) 0.0294(2) 0.02815(19) 0.00422(13) 0.00555(15) 0.00051(14) C1 0.0233(14) 0.0216(14) 0.0337(16) 0.0034(12) -0.0027(12) -0.0083(11) C2 0.0264(14) 0.0205(14) 0.0308(15) 0.0043(11) -0.0003(12) -0.0033(11) C3 0.0353(16) 0.0232(14) 0.0255(14) 0.0017(11) 0.0007(12) -0.0020(12) C4 0.0304(15) 0.0189(13) 0.0339(15) 0.0050(11) 0.0034(12) -0.0013(11) C5 0.0366(16) 0.0256(15) 0.0288(15) 0.0062(12) -0.0014(13) 0.0013(12) C6 0.0400(17) 0.0274(15) 0.0269(15) -0.0010(12) -0.0016(13) -0.0012(13) C7 0.0285(15) 0.0190(14) 0.0349(16) 0.0010(11) -0.0013(12) -0.0032(11) C8 0.0402(18) 0.0317(17) 0.0337(16) -0.0039(13) -0.0108(14) 0.0076(14) C9 0.0325(16) 0.0228(14) 0.0297(15) 0.0025(12) 0.0021(13) -0.0026(12) C10 0.0266(15) 0.0184(13) 0.0293(15) 0.0001(11) 0.0040(12) 0.0018(11) C11 0.0225(13) 0.0199(13) 0.0232(13) 0.0008(10) 0.0017(11) 0.0020(10) C12 0.0241(14) 0.0213(14) 0.0319(15) 0.0034(11) 0.0016(12) 0.0042(11) C13 0.0323(15) 0.0194(14) 0.0283(15) 0.0024(11) 0.0034(12) -0.0010(11) C14 0.0260(15) 0.0275(15) 0.0362(16) 0.0059(12) 0.0087(12) -0.0002(12) C15 0.0234(14) 0.0284(15) 0.0361(16) 0.0055(12) 0.0046(12) 0.0054(12) C16 0.0267(14) 0.0191(13) 0.0259(14) 0.0015(11) 0.0020(11) 0.0022(11) C17 0.0211(14) 0.0238(14) 0.0287(15) 0.0046(11) 0.0050(11) 0.0030(11) C18 0.0317(17) 0.0411(18) 0.0442(18) 0.0184(15) 0.0015(14) 0.0046(14) C19 0.0286(16) 0.049(2) 0.0483(19) 0.0198(16) 0.0062(14) -0.0005(14) C20 0.0354(17) 0.0335(17) 0.060(2) 0.0169(15) 0.0237(16) 0.0107(14) C21 0.0406(18) 0.0301(17) 0.062(2) 0.0162(15) 0.0210(17) 0.0118(14) C22 0.0307(15) 0.0219(14) 0.0290(15) 0.0003(11) 0.0058(12) -0.0007(11) C23 0.0296(15) 0.0236(14) 0.0287(14) 0.0027(11) 0.0049(12) -0.0015(12) C24 0.0263(16) 0.0446(19) 0.0482(19) 0.0158(15) 0.0110(14) 0.0037(14) C25 0.0305(16) 0.0384(18) 0.0449(18) 0.0185(14) 0.0047(14) 0.0045(13) C26 0.0353(17) 0.0336(17) 0.052(2) 0.0197(15) 0.0119(15) 0.0096(14) C27 0.0285(16) 0.0377(17) 0.0505(19) 0.0140(15) 0.0128(14) 0.0028(13) C28 0.100(4) 0.053(3) 0.071(3) -0.011(2) 0.033(3) -0.004(2) C29 0.084(3) 0.053(2) 0.079(3) -0.012(2) 0.035(3) -0.017(2) C30 0.052(2) 0.049(2) 0.0328(17) 0.0054(15) -0.0001(15) 0.0027(17) C31 0.054(3) 0.092(3) 0.067(3) -0.030(3) 0.000(2) -0.007(2) C32 0.051(3) 0.115(4) 0.077(3) -0.028(3) 0.012(2) -0.012(3) N1 0.0329(13) 0.0233(12) 0.0264(12) 0.0018(10) 0.0070(10) -0.0007(10) N2 0.0296(13) 0.0245(12) 0.0279(12) 0.0030(10) 0.0038(10) -0.0030(10) N3 0.075(3) 0.076(2) 0.053(2) -0.0010(19) 0.0155(18) 0.010(2) O1 0.0284(11) 0.0392(12) 0.0273(11) 0.0031(9) -0.0026(8) 0.0006(9) O2 0.0373(12) 0.0375(12) 0.0403(12) -0.0027(10) -0.0070(10) 0.0105(10) O3 0.0427(13) 0.0217(11) 0.0654(15) 0.0002(10) -0.0099(11) 0.0005(10) O4 0.0658(17) 0.0495(15) 0.0428(13) -0.0028(11) 0.0092(13) 0.0183(13) O5 0.0557(15) 0.0327(12) 0.0366(12) 0.0071(9) 0.0170(11) 0.0058(10) O6 0.0230(10) 0.0427(12) 0.0329(11) 0.0127(9) 0.0014(9) -0.0004(9) O7 0.0328(12) 0.0587(14) 0.0290(11) 0.0162(10) -0.0017(9) -0.0130(10) O8 0.0549(14) 0.0393(12) 0.0270(11) 0.0061(9) 0.0092(10) 0.0234(11) O9 0.0404(12) 0.0215(10) 0.0306(10) 0.0023(8) 0.0053(9) 0.0077(9) O1W 0.0377(12) 0.0372(12) 0.0388(12) 0.0012(10) 0.0020(10) 0.0024(10) _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 O1 1.9570(19) 2_544 y Zn1 O6 1.9581(19) . y Zn1 O9 1.9786(19) 3_655 y Zn1 N2 2.044(2) 2 y Zn2 O8 1.996(2) . y Zn2 N1 2.050(2) . y Zn2 O7 2.051(2) . y Zn2 O3 2.080(2) 3_665 y Zn2 O1W 2.143(2) . y Zn2 O4 2.315(3) 3_665 y Zn2 C8 2.498(3) 3_665 y C1 O2 1.233(4) . ? C1 O1 1.270(3) . ? C1 C2 1.519(4) . ? C2 C3 1.383(4) . ? C2 C7 1.401(4) . ? C3 C4 1.395(4) . ? C3 H3 0.9300 . ? C4 C5 1.386(4) . ? C4 C9 1.497(4) . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.386(4) . ? C6 H6 0.9300 . ? C7 C8 1.510(4) . ? C8 O4 1.234(4) . ? C8 O3 1.264(4) . ? C8 Zn2 2.498(3) 3_665 y C9 O5 1.208(4) . ? C9 C13 1.498(4) . ? C10 O7 1.243(3) . ? C10 O6 1.254(3) . ? C10 C11 1.509(4) . ? C11 C12 1.399(4) . ? C11 C16 1.401(4) . ? C12 C13 1.388(4) . ? C12 H12 0.9300 . ? C13 C14 1.390(4) . ? C14 C15 1.384(4) . ? C14 H14 0.9300 . ? C15 C16 1.390(4) . ? C15 H15 0.9300 . ? C16 C17 1.514(4) . ? C17 O8 1.245(3) . ? C17 O9 1.254(3) . ? C18 N1 1.330(4) . ? C18 C19 1.373(4) . ? C18 H18 0.9300 . ? C19 C22 1.385(4) . ? C19 H19 0.9300 . ? C20 N1 1.323(4) . ? C20 C21 1.373(4) . ? C20 H20 0.9300 . ? C21 C22 1.382(4) . ? C21 H21 0.9300 . ? C22 C23 1.488(4) . ? C23 C26 1.383(4) . ? C23 C24 1.390(4) . ? C24 C25 1.377(4) . ? C24 H24 0.9300 . ? C25 N2 1.334(4) . ? C25 H25 0.9300 . ? C26 C27 1.372(4) . ? C26 H26 0.9300 . ? C27 N2 1.334(4) . ? C27 H27 0.9300 . ? C28 N3 1.328(6) . ? C28 C29 1.382(6) . ? C28 H28 0.9300 . ? C29 C30 1.367(5) . ? C29 H29 0.9300 . ? C30 C31 1.379(6) . ? C30 C30 1.483(7) 3_567 ? C31 C32 1.376(6) . ? C31 H31 0.9300 . ? C32 N3 1.338(6) . ? C32 H32 0.9300 . ? N2 Zn1 2.044(2) 2_545 y O1 Zn1 1.9570(19) 2_554 y O3 Zn2 2.081(2) 3_665 y O4 Zn2 2.315(3) 3_665 y O9 Zn1 1.9787(19) 3_655 y O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? 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 O1 Zn1 O6 117.77(8) 2_544 . y O1 Zn1 O9 107.59(9) 2_544 3_655 y O6 Zn1 O9 113.81(8) . 3_655 y O1 Zn1 N2 105.95(9) 2_544 2 y O6 Zn1 N2 108.57(9) . 2 y O9 Zn1 N2 101.66(8) 3_655 2 y O8 Zn2 N1 94.53(9) . . y O8 Zn2 O7 88.06(9) . . y N1 Zn2 O7 90.58(9) . . y O8 Zn2 O3 167.27(9) . 3_665 y N1 Zn2 O3 97.98(9) . 3_665 y O7 Zn2 O3 89.47(9) . 3_665 y O8 Zn2 O1W 92.27(9) . . y N1 Zn2 O1W 94.46(9) . . y O7 Zn2 O1W 174.91(8) . . y O3 Zn2 O1W 89.11(8) 3_665 . y O8 Zn2 O4 108.03(9) . 3_665 y N1 Zn2 O4 157.11(9) . 3_665 y O7 Zn2 O4 93.92(9) . 3_665 y O3 Zn2 O4 59.69(9) 3_665 3_665 y O1W Zn2 O4 81.15(9) . 3_665 y O8 Zn2 C8 137.41(11) . 3_665 y N1 Zn2 C8 128.01(10) . 3_665 y O7 Zn2 C8 92.96(10) . 3_665 y O3 Zn2 C8 30.33(10) 3_665 3_665 y O1W Zn2 C8 83.36(9) . 3_665 y O4 Zn2 C8 29.39(10) 3_665 3_665 y O2 C1 O1 124.7(3) . . ? O2 C1 C2 119.0(3) . . ? O1 C1 C2 116.2(2) . . ? C3 C2 C7 119.2(3) . . ? C3 C2 C1 119.5(3) . . ? C7 C2 C1 121.0(2) . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 C9 121.9(3) . . ? C3 C4 C9 118.1(3) . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 119.7(3) . . ? C6 C7 C8 118.7(3) . . ? C2 C7 C8 121.4(3) . . ? O4 C8 O3 123.2(3) . . ? O4 C8 C7 119.9(3) . . ? O3 C8 C7 116.9(3) . . ? O4 C8 Zn2 67.06(18) . 3_665 ? O3 C8 Zn2 56.22(16) . 3_665 ? C7 C8 Zn2 173.0(2) . 3_665 ? O5 C9 C4 119.2(3) . . ? O5 C9 C13 120.2(3) . . ? C4 C9 C13 120.5(2) . . ? O7 C10 O6 122.9(3) . . ? O7 C10 C11 121.2(2) . . ? O6 C10 C11 115.8(2) . . ? C12 C11 C16 118.5(2) . . ? C12 C11 C10 117.3(2) . . ? C16 C11 C10 124.1(2) . . ? C13 C12 C11 121.4(3) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 119.3(2) . . ? C12 C13 C9 122.3(3) . . ? C14 C13 C9 118.2(3) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 119.9(2) . . ? C15 C16 C17 114.9(2) . . ? C11 C16 C17 125.2(2) . . ? O8 C17 O9 123.1(2) . . ? O8 C17 C16 121.3(2) . . ? O9 C17 C16 115.4(2) . . ? N1 C18 C19 122.5(3) . . ? N1 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C22 120.8(3) . . ? C18 C19 H19 119.6 . . ? C22 C19 H19 119.6 . . ? N1 C20 C21 123.7(3) . . ? N1 C20 H20 118.2 . . ? C21 C20 H20 118.2 . . ? C20 C21 C22 120.0(3) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C19 115.8(3) . . ? C21 C22 C23 122.0(3) . . ? C19 C22 C23 122.2(3) . . ? C26 C23 C24 116.2(3) . . ? C26 C23 C22 121.3(3) . . ? C24 C23 C22 122.5(3) . . ? C25 C24 C23 120.0(3) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? N2 C25 C24 123.3(3) . . ? N2 C25 H25 118.3 . . ? C24 C25 H25 118.3 . . ? C27 C26 C23 120.3(3) . . ? C27 C26 H26 119.8 . . ? C23 C26 H26 119.8 . . ? N2 C27 C26 123.4(3) . . ? N2 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? N3 C28 C29 124.1(4) . . ? N3 C28 H28 118.0 . . ? C29 C28 H28 117.9 . . ? C30 C29 C28 120.4(4) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 116.5(4) . . ? C29 C30 C30 121.9(4) . 3_567 ? C31 C30 C30 121.6(4) . 3_567 ? C32 C31 C30 119.4(4) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? N3 C32 C31 124.9(5) . . ? N3 C32 H32 117.6 . . ? C31 C32 H32 117.6 . . ? C20 N1 C18 117.0(2) . . ? C20 N1 Zn2 122.0(2) . . ? C18 N1 Zn2 120.82(19) . . ? C27 N2 C25 116.7(2) . . ? C27 N2 Zn1 120.59(19) . 2_545 ? C25 N2 Zn1 122.6(2) . 2_545 ? C28 N3 C32 114.7(4) . . ? C1 O1 Zn1 116.05(18) . 2_554 ? C8 O3 Zn2 93.5(2) . 3_665 ? C8 O4 Zn2 83.6(2) . 3_665 ? C10 O6 Zn1 122.14(18) . . ? C10 O7 Zn2 130.07(19) . . ? C17 O8 Zn2 129.35(18) . . ? C17 O9 Zn1 116.00(17) . 3_655 ? Zn2 O1W H1WA 108.3 . . ? Zn2 O1W H1WB 119.0 . . ? H1WA O1W H1WB 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 159.0(3) . . . . ? O1 C1 C2 C3 -17.0(4) . . . . ? O2 C1 C2 C7 -14.9(4) . . . . ? O1 C1 C2 C7 169.2(2) . . . . ? C7 C2 C3 C4 2.5(4) . . . . ? C1 C2 C3 C4 -171.5(3) . . . . ? C2 C3 C4 C5 1.3(4) . . . . ? C2 C3 C4 C9 -172.2(3) . . . . ? C3 C4 C5 C6 -4.0(4) . . . . ? C9 C4 C5 C6 169.2(3) . . . . ? C4 C5 C6 C7 2.9(4) . . . . ? C5 C6 C7 C2 0.9(4) . . . . ? C5 C6 C7 C8 -174.4(3) . . . . ? C3 C2 C7 C6 -3.6(4) . . . . ? C1 C2 C7 C6 170.3(3) . . . . ? C3 C2 C7 C8 171.7(3) . . . . ? C1 C2 C7 C8 -14.5(4) . . . . ? C6 C7 C8 O4 -62.4(4) . . . . ? C2 C7 C8 O4 122.3(3) . . . . ? C6 C7 C8 O3 115.1(3) . . . . ? C2 C7 C8 O3 -60.1(4) . . . . ? C5 C4 C9 O5 -142.7(3) . . . . ? C3 C4 C9 O5 30.6(4) . . . . ? C5 C4 C9 C13 34.0(4) . . . . ? C3 C4 C9 C13 -152.7(3) . . . . ? O7 C10 C11 C12 -145.1(3) . . . . ? O6 C10 C11 C12 33.5(4) . . . . ? O7 C10 C11 C16 38.6(4) . . . . ? O6 C10 C11 C16 -142.8(3) . . . . ? C16 C11 C12 C13 0.9(4) . . . . ? C10 C11 C12 C13 -175.6(2) . . . . ? C11 C12 C13 C14 2.9(4) . . . . ? C11 C12 C13 C9 178.3(3) . . . . ? O5 C9 C13 C12 -143.5(3) . . . . ? C4 C9 C13 C12 39.9(4) . . . . ? O5 C9 C13 C14 32.0(4) . . . . ? C4 C9 C13 C14 -144.7(3) . . . . ? C12 C13 C14 C15 -3.5(4) . . . . ? C9 C13 C14 C15 -179.1(3) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C11 3.5(4) . . . . ? C14 C15 C16 C17 -178.3(3) . . . . ? C12 C11 C16 C15 -4.1(4) . . . . ? C10 C11 C16 C15 172.1(3) . . . . ? C12 C11 C16 C17 177.9(3) . . . . ? C10 C11 C16 C17 -5.8(4) . . . . ? C15 C16 C17 O8 120.2(3) . . . . ? C11 C16 C17 O8 -61.8(4) . . . . ? C15 C16 C17 O9 -54.9(3) . . . . ? C11 C16 C17 O9 123.1(3) . . . . ? N1 C18 C19 C22 -0.4(5) . . . . ? N1 C20 C21 C22 1.0(6) . . . . ? C20 C21 C22 C19 2.7(5) . . . . ? C20 C21 C22 C23 -175.8(3) . . . . ? C18 C19 C22 C21 -3.0(5) . . . . ? C18 C19 C22 C23 175.5(3) . . . . ? C21 C22 C23 C26 175.3(3) . . . . ? C19 C22 C23 C26 -3.1(5) . . . . ? C21 C22 C23 C24 -3.7(5) . . . . ? C19 C22 C23 C24 177.8(3) . . . . ? C26 C23 C24 C25 -0.6(5) . . . . ? C22 C23 C24 C25 178.6(3) . . . . ? C23 C24 C25 N2 -0.4(5) . . . . ? C24 C23 C26 C27 0.3(5) . . . . ? C22 C23 C26 C27 -178.8(3) . . . . ? C23 C26 C27 N2 1.0(5) . . . . ? N3 C28 C29 C30 -0.1(8) . . . . ? C28 C29 C30 C31 0.4(7) . . . . ? C28 C29 C30 C30 178.7(4) . . . 3_567 ? C29 C30 C31 C32 -0.7(6) . . . . ? C30 C30 C31 C32 -178.9(5) 3_567 . . . ? C30 C31 C32 N3 0.6(8) . . . . ? C21 C20 N1 C18 -4.4(5) . . . . ? C21 C20 N1 Zn2 171.5(3) . . . . ? C19 C18 N1 C20 4.0(5) . . . . ? C19 C18 N1 Zn2 -171.9(3) . . . . ? O8 Zn2 N1 C20 44.5(3) . . . . ? O7 Zn2 N1 C20 132.6(2) . . . . ? O3 Zn2 N1 C20 -137.9(2) 3_665 . . . ? O1W Zn2 N1 C20 -48.1(2) . . . . ? O4 Zn2 N1 C20 -125.9(3) 3_665 . . . ? C8 Zn2 N1 C20 -133.2(2) 3_665 . . . ? O8 Zn2 N1 C18 -139.8(2) . . . . ? O7 Zn2 N1 C18 -51.7(2) . . . . ? O3 Zn2 N1 C18 37.9(2) 3_665 . . . ? O1W Zn2 N1 C18 127.6(2) . . . . ? O4 Zn2 N1 C18 49.8(4) 3_665 . . . ? C8 Zn2 N1 C18 42.5(3) 3_665 . . . ? C26 C27 N2 C25 -1.9(5) . . . . ? C26 C27 N2 Zn1 -179.1(3) . . . 2_545 ? C24 C25 N2 C27 1.7(5) . . . . ? C24 C25 N2 Zn1 178.8(3) . . . 2_545 ? C29 C28 N3 C32 0.0(7) . . . . ? C31 C32 N3 C28 -0.3(7) . . . . ? O2 C1 O1 Zn1 -20.1(4) . . . 2_554 ? C2 C1 O1 Zn1 155.61(18) . . . 2_554 ? O4 C8 O3 Zn2 -3.8(3) . . . 3_665 ? C7 C8 O3 Zn2 178.8(2) . . . 3_665 ? O3 C8 O4 Zn2 3.4(3) . . . 3_665 ? C7 C8 O4 Zn2 -179.3(3) . . . 3_665 ? O7 C10 O6 Zn1 -7.2(4) . . . . ? C11 C10 O6 Zn1 174.25(17) . . . . ? O1 Zn1 O6 C10 -157.6(2) 2_544 . . . ? O9 Zn1 O6 C10 -30.3(2) 3_655 . . . ? N2 Zn1 O6 C10 82.1(2) 2 . . . ? O6 C10 O7 Zn2 -155.5(2) . . . . ? C11 C10 O7 Zn2 23.0(4) . . . . ? O8 Zn2 O7 C10 -69.4(3) . . . . ? N1 Zn2 O7 C10 -163.9(3) . . . . ? O3 Zn2 O7 C10 98.2(3) 3_665 . . . ? O4 Zn2 O7 C10 38.6(3) 3_665 . . . ? C8 Zn2 O7 C10 68.0(3) 3_665 . . . ? O9 C17 O8 Zn2 -150.8(2) . . . . ? C16 C17 O8 Zn2 34.4(4) . . . . ? N1 Zn2 O8 C17 121.8(3) . . . . ? O7 Zn2 O8 C17 31.3(3) . . . . ? O3 Zn2 O8 C17 -47.6(6) 3_665 . . . ? O1W Zn2 O8 C17 -143.6(3) . . . . ? O4 Zn2 O8 C17 -62.1(3) 3_665 . . . ? C8 Zn2 O8 C17 -60.9(3) 3_665 . . . ? O8 C17 O9 Zn1 12.9(4) . . . 3_655 ? C16 C17 O9 Zn1 -172.08(17) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.587 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 871939'