# 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_Solid4a _audit_creation_method 'SHELXTL-NT2000 ver.6.12' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 N12 Na2 O34 Zn5' _chemical_formula_sum 'C30 H24 N12 Na2 O34 Zn5' _chemical_formula_weight 1469.54 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.7539(15) _cell_length_b 19.227(3) _cell_length_c 24.684(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4629.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5174 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.93 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.524 _exptl_crystal_size_mid 0.324 _exptl_crystal_size_min 0.184 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2928 _exptl_absorpt_coefficient_mu 2.699 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.363 _exptl_absorpt_correction_T_max 0.610 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41603 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4077 _reflns_number_gt 3635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+16.9444P] 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 4077 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.003 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 0.79588(5) 0.17441(3) 0.62315(2) 0.02402(18) Uani 1 1 d . . . Zn2 Zn 0.85151(5) 0.02613(3) 0.34539(2) 0.02495(19) Uani 1 1 d . . . Zn3 Zn 0.56255(13) 0.01131(7) 0.49957(5) 0.0354(3) Uani 0.50 1 d P . . Na1 Na 0.4665(2) 0.08284(10) 0.29477(8) 0.0349(5) Uani 1 1 d . . . O1 O 0.7506(4) 0.03763(18) 0.41617(14) 0.0333(8) Uani 1 1 d . . . O2 O 0.7740(4) 0.0369(2) 0.50530(16) 0.0544(12) Uani 1 1 d . . . O3 O 1.0118(3) 0.04540(16) 0.29722(12) 0.0242(7) Uani 1 1 d . . . O4 O 1.2378(3) 0.0473(2) 0.29528(14) 0.0361(8) Uani 1 1 d . . . O5 O 0.7319(4) 0.11152(17) 0.31832(14) 0.0324(8) Uani 1 1 d . . . O6 O 0.7421(4) -0.03297(17) 0.29267(14) 0.0325(8) Uani 1 1 d . . . O7 O 0.9564(4) -0.06116(18) 0.37674(16) 0.0387(9) Uani 1 1 d . . . O8 O 1.3622(3) 0.18473(18) 0.25570(15) 0.0346(8) Uani 1 1 d . . . O9 O 0.8412(4) 0.29848(19) 0.53825(14) 0.0376(8) Uani 1 1 d . . . O10 O 0.7007(3) 0.21075(18) 0.55936(13) 0.0311(7) Uani 1 1 d . . . O11 O 0.9833(4) 0.16498(18) 0.59657(16) 0.0394(9) Uani 1 1 d . . . O12 O 0.8598(4) 0.2359(2) 0.68014(15) 0.0402(9) Uani 1 1 d . . . O13 O 0.6802(3) 0.09371(16) 0.63663(14) 0.0307(7) Uani 1 1 d . . . O14 O 0.5081(3) 0.03003(16) 0.66468(15) 0.0331(8) Uani 1 1 d . . . O15 O 0.4973(6) 0.1100(2) 0.52071(17) 0.0661(14) Uani 1 1 d . . . O16 O 0.4562(7) 0.0243(2) 0.4346(2) 0.085(2) Uani 1 1 d . . . N1 N 1.0073(4) 0.09837(17) 0.40238(15) 0.0213(8) Uani 1 1 d . . . N2 N 1.0471(4) 0.19547(18) 0.34905(14) 0.0185(7) Uani 1 1 d . . . N3 N 1.0850(4) 0.29526(19) 0.29952(15) 0.0229(8) Uani 1 1 d . . . N4 N 0.9112(4) 0.29766(18) 0.36297(14) 0.0197(7) Uani 1 1 d . . . N5 N 0.7465(4) 0.29601(18) 0.43060(14) 0.0194(7) Uani 1 1 d . . . N6 N 0.8787(4) 0.19799(18) 0.41927(14) 0.0201(7) Uani 1 1 d . . . C1 C 0.8186(5) 0.0481(3) 0.4589(2) 0.0331(12) Uani 1 1 d . . . C2 C 0.9652(5) 0.0744(2) 0.45545(18) 0.0278(10) Uani 1 1 d . . . H2A H 0.9762 0.1124 0.4810 0.033 Uiso 1 1 calc R . . H2B H 1.0263 0.0373 0.4667 0.033 Uiso 1 1 calc R . . C3 C 1.1278(4) 0.0541(2) 0.31946(18) 0.0233(9) Uani 1 1 d . . . C4 C 1.1353(4) 0.0714(2) 0.37948(18) 0.0241(9) Uani 1 1 d . . . H4A H 1.1612 0.0298 0.3992 0.029 Uiso 1 1 calc R . . H4B H 1.2070 0.1057 0.3850 0.029 Uiso 1 1 calc R . . C5 C 0.9304(5) -0.1182(2) 0.39643(18) 0.0241(9) Uani 1 1 d . . . C6 C 0.9761(4) 0.1680(2) 0.38971(17) 0.0196(9) Uani 1 1 d . . . C7 C 1.0106(4) 0.2612(2) 0.33851(16) 0.0184(8) Uani 1 1 d . . . C8 C 1.0490(5) 0.3663(2) 0.28653(18) 0.0244(9) Uani 1 1 d . . . H8A H 0.9518 0.3686 0.2785 0.029 Uiso 1 1 calc R . . H8B H 1.0986 0.3805 0.2543 0.029 Uiso 1 1 calc R . . C9 C 1.1635(5) 0.2539(2) 0.26099(18) 0.0262(10) Uani 1 1 d . . . H9A H 1.1740 0.2804 0.2278 0.031 Uiso 1 1 calc R . . H9B H 1.1116 0.2123 0.2523 0.031 Uiso 1 1 calc R . . C10 C 1.3040(5) 0.2324(2) 0.28066(18) 0.0259(10) Uani 1 1 d . . . C11 C 0.8485(4) 0.2633(2) 0.40342(16) 0.0179(8) Uani 1 1 d . . . C12 C 0.7129(4) 0.3689(2) 0.41983(18) 0.0209(9) Uani 1 1 d . . . H12A H 0.7802 0.3875 0.3947 0.025 Uiso 1 1 calc R . . H12B H 0.7214 0.3948 0.4534 0.025 Uiso 1 1 calc R . . C13 C 0.6751(4) 0.2590(2) 0.47343(17) 0.0214(9) Uani 1 1 d . . . H13A H 0.6597 0.2116 0.4616 0.026 Uiso 1 1 calc R . . H13B H 0.5861 0.2805 0.4786 0.026 Uiso 1 1 calc R . . C14 C 0.7485(5) 0.2572(2) 0.52770(18) 0.0253(10) Uani 1 1 d . . . C15 C 0.5813(5) 0.0831(2) 0.66781(19) 0.0248(10) Uani 1 1 d . . . O17 O 0.5089(4) 0.1609(2) 0.37068(16) 0.0487(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0226(3) 0.0238(3) 0.0257(3) 0.0024(2) 0.0019(2) -0.0023(2) Zn2 0.0187(3) 0.0269(3) 0.0293(3) 0.0056(2) 0.0022(2) 0.0003(2) Zn3 0.0309(6) 0.0481(7) 0.0272(6) 0.0086(5) 0.0037(5) 0.0087(5) Na1 0.0310(10) 0.0363(11) 0.0374(11) 0.0000(8) 0.0008(8) 0.0010(8) O1 0.0248(17) 0.0382(19) 0.0369(19) 0.0105(15) 0.0086(16) 0.0037(15) O2 0.047(2) 0.080(3) 0.037(2) 0.027(2) 0.0220(19) 0.022(2) O3 0.0210(16) 0.0288(16) 0.0227(15) 0.0015(12) 0.0008(13) -0.0003(13) O4 0.0203(17) 0.055(2) 0.0333(18) 0.0000(16) 0.0066(15) 0.0015(16) O5 0.0323(18) 0.0310(18) 0.0338(18) 0.0054(14) 0.0010(15) 0.0081(15) O6 0.0262(17) 0.0323(18) 0.0389(19) -0.0033(14) -0.0014(15) -0.0019(14) O7 0.0254(18) 0.035(2) 0.056(2) 0.0178(17) 0.0046(16) -0.0016(15) O8 0.0282(18) 0.0372(19) 0.0383(19) -0.0092(16) 0.0009(15) 0.0060(15) O9 0.042(2) 0.042(2) 0.0296(18) 0.0035(15) -0.0081(16) -0.0109(17) O10 0.0311(18) 0.0382(19) 0.0242(16) 0.0101(14) 0.0010(14) 0.0013(15) O11 0.0287(19) 0.0354(19) 0.054(2) 0.0143(17) 0.0138(17) 0.0077(15) O12 0.0289(19) 0.049(2) 0.043(2) -0.0199(18) 0.0032(16) -0.0088(16) O13 0.0296(18) 0.0218(16) 0.0406(19) 0.0009(14) 0.0076(15) -0.0037(14) O14 0.0268(18) 0.0225(17) 0.050(2) 0.0010(15) 0.0034(16) -0.0060(14) O15 0.099(4) 0.054(3) 0.046(2) -0.007(2) -0.007(3) 0.036(3) O16 0.152(6) 0.039(2) 0.065(3) -0.012(2) -0.056(4) 0.017(3) N1 0.0219(19) 0.0155(17) 0.0265(19) 0.0002(14) 0.0057(15) 0.0042(14) N2 0.0182(18) 0.0151(16) 0.0223(18) 0.0011(14) 0.0017(14) 0.0003(14) N3 0.0222(19) 0.0195(18) 0.0271(19) 0.0012(15) 0.0108(16) 0.0020(15) N4 0.0204(18) 0.0188(17) 0.0199(17) 0.0011(14) 0.0041(15) 0.0023(14) N5 0.0203(18) 0.0187(17) 0.0193(17) 0.0038(14) 0.0042(15) 0.0042(14) N6 0.0219(18) 0.0168(17) 0.0215(18) 0.0019(14) 0.0033(15) 0.0014(14) C1 0.035(3) 0.028(2) 0.036(3) 0.015(2) 0.012(2) 0.017(2) C2 0.034(3) 0.028(2) 0.022(2) 0.0054(18) 0.0002(19) 0.009(2) C3 0.022(2) 0.020(2) 0.028(2) 0.0068(18) 0.0022(19) 0.0030(17) C4 0.018(2) 0.026(2) 0.028(2) 0.0038(18) -0.0032(18) 0.0034(18) C5 0.029(2) 0.019(2) 0.023(2) 0.0030(17) -0.0010(19) 0.0043(19) C6 0.019(2) 0.017(2) 0.022(2) -0.0011(16) -0.0042(17) 0.0011(16) C7 0.017(2) 0.019(2) 0.019(2) -0.0029(16) -0.0015(16) -0.0017(16) C8 0.023(2) 0.022(2) 0.029(2) 0.0072(18) 0.0017(18) 0.0023(18) C9 0.024(2) 0.031(2) 0.024(2) -0.0014(18) 0.0048(19) 0.0018(19) C10 0.022(2) 0.027(2) 0.029(2) 0.001(2) 0.0060(19) -0.0003(18) C11 0.016(2) 0.019(2) 0.019(2) -0.0003(16) -0.0017(16) -0.0021(16) C12 0.020(2) 0.018(2) 0.025(2) 0.0007(17) 0.0008(17) 0.0015(16) C13 0.020(2) 0.022(2) 0.022(2) 0.0017(17) 0.0038(17) 0.0017(17) C14 0.024(2) 0.027(2) 0.024(2) 0.0032(19) 0.0054(19) 0.007(2) C15 0.020(2) 0.021(2) 0.033(2) 0.0091(18) -0.0033(19) 0.0015(18) O17 0.038(2) 0.066(3) 0.042(2) -0.0111(19) 0.0012(17) 0.011(2) _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 O12 1.940(3) . ? Zn1 O13 1.947(3) . ? Zn1 O11 1.951(3) . ? Zn1 O10 1.957(3) . ? Zn2 O3 1.998(3) . ? Zn2 O1 2.017(3) . ? Zn2 O6 2.031(3) . ? Zn2 O7 2.112(3) . ? Zn2 O5 2.122(3) . ? Zn2 N1 2.494(4) . ? Zn3 Zn3 1.296(3) 5_656 ? Zn3 O16 1.773(6) 5_656 ? Zn3 O16 1.926(5) . ? Zn3 O15 2.068(4) . ? Zn3 O2 2.125(5) . ? Zn3 O15 2.456(5) 5_656 ? Na1 O4 2.333(4) 1_455 ? Na1 O14 2.403(4) 5_656 ? Na1 O8 2.409(4) 1_455 ? Na1 O3 2.423(4) 6_556 ? Na1 O17 2.436(4) . ? Na1 O5 2.710(4) . ? O1 C1 1.262(7) . ? O2 C1 1.244(6) . ? O3 C3 1.269(6) . ? O3 Na1 2.423(4) 6_656 ? O4 C3 1.235(6) . ? O4 Na1 2.333(4) 1_655 ? O7 C5 1.226(5) . ? O8 C10 1.241(6) . ? O8 Na1 2.409(4) 1_655 ? O9 C14 1.232(6) . ? O10 C14 1.275(6) . ? O11 C5 1.245(6) 5_756 ? O12 C10 1.267(6) 4_456 ? O13 C15 1.251(6) . ? O14 C15 1.248(5) . ? O14 Na1 2.403(4) 5_656 ? O15 Zn3 2.456(5) 5_656 ? O16 Zn3 1.773(6) 5_656 ? N1 C6 1.408(5) . ? N1 C2 1.448(6) . ? N1 C4 1.464(5) . ? N2 C6 1.329(6) . ? N2 C7 1.339(5) . ? N3 C7 1.372(5) . ? N3 C8 1.447(6) . ? N3 C9 1.457(6) . ? N4 C7 1.340(5) . ? N4 C11 1.345(5) . ? N5 C11 1.355(5) . ? N5 C13 1.452(5) . ? N5 C12 1.464(5) . ? N6 C6 1.329(6) . ? N6 C11 1.347(5) . ? C1 C2 1.520(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.520(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O11 1.245(6) 5_756 ? C5 C12 1.532(6) 8_755 ? C8 C15 1.521(7) 4_556 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.511(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O12 1.267(6) 4_556 ? C12 C5 1.532(6) 8_765 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.519(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C15 C8 1.521(7) 4_456 ? 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 O12 Zn1 O13 123.20(16) . . ? O12 Zn1 O11 89.95(16) . . ? O13 Zn1 O11 121.78(14) . . ? O12 Zn1 O10 121.23(16) . . ? O13 Zn1 O10 98.46(15) . . ? O11 Zn1 O10 101.95(15) . . ? O3 Zn2 O1 151.21(14) . . ? O3 Zn2 O6 97.69(13) . . ? O1 Zn2 O6 111.09(14) . . ? O3 Zn2 O7 89.22(13) . . ? O1 Zn2 O7 90.34(14) . . ? O6 Zn2 O7 92.56(15) . . ? O3 Zn2 O5 95.69(13) . . ? O1 Zn2 O5 85.40(13) . . ? O6 Zn2 O5 86.69(14) . . ? O7 Zn2 O5 175.08(14) . . ? O3 Zn2 N1 75.85(12) . . ? O1 Zn2 N1 75.39(13) . . ? O6 Zn2 N1 173.49(13) . . ? O7 Zn2 N1 86.60(13) . . ? O5 Zn2 N1 94.69(13) . . ? Zn3 Zn3 O16 76.0(2) 5_656 5_656 ? Zn3 Zn3 O16 63.3(2) 5_656 . ? O16 Zn3 O16 139.26(13) 5_656 . ? Zn3 Zn3 O15 90.8(2) 5_656 . ? O16 Zn3 O15 95.2(2) 5_656 . ? O16 Zn3 O15 85.74(19) . . ? Zn3 Zn3 O2 172.18(17) 5_656 . ? O16 Zn3 O2 97.4(2) 5_656 . ? O16 Zn3 O2 123.2(2) . . ? O15 Zn3 O2 94.0(2) . . ? Zn3 Zn3 O15 57.35(16) 5_656 5_656 ? O16 Zn3 O15 78.21(18) 5_656 5_656 ? O16 Zn3 O15 79.93(18) . 5_656 ? O15 Zn3 O15 148.16(9) . 5_656 ? O2 Zn3 O15 117.65(18) . 5_656 ? O4 Na1 O14 80.33(14) 1_455 5_656 ? O4 Na1 O8 80.57(14) 1_455 1_455 ? O14 Na1 O8 160.87(15) 5_656 1_455 ? O4 Na1 O3 95.30(13) 1_455 6_556 ? O14 Na1 O3 95.93(13) 5_656 6_556 ? O8 Na1 O3 86.75(13) 1_455 6_556 ? O4 Na1 O17 109.78(15) 1_455 . ? O14 Na1 O17 102.62(15) 5_656 . ? O8 Na1 O17 83.03(14) 1_455 . ? O3 Na1 O17 150.82(16) 6_556 . ? O4 Na1 O5 166.36(14) 1_455 . ? O14 Na1 O5 89.76(12) 5_656 . ? O8 Na1 O5 108.91(13) 1_455 . ? O3 Na1 O5 95.03(12) 6_556 . ? O17 Na1 O5 63.10(13) . . ? C1 O1 Zn2 119.0(3) . . ? C1 O2 Zn3 108.6(4) . . ? C3 O3 Zn2 117.7(3) . . ? C3 O3 Na1 121.9(3) . 6_656 ? Zn2 O3 Na1 118.05(15) . 6_656 ? C3 O4 Na1 143.4(3) . 1_655 ? Zn2 O5 Na1 115.80(15) . . ? C5 O7 Zn2 139.1(3) . . ? C10 O8 Na1 126.5(3) . 1_655 ? C14 O10 Zn1 124.8(3) . . ? C5 O11 Zn1 130.9(3) 5_756 . ? C10 O12 Zn1 135.2(3) 4_456 . ? C15 O13 Zn1 133.0(3) . . ? C15 O14 Na1 130.8(3) . 5_656 ? C6 N1 C2 116.2(3) . . ? C6 N1 C4 115.8(4) . . ? C2 N1 C4 118.6(3) . . ? C6 N1 Zn2 105.8(3) . . ? C2 N1 Zn2 99.2(3) . . ? C4 N1 Zn2 96.0(2) . . ? C6 N2 C7 112.5(4) . . ? C7 N3 C8 118.5(3) . . ? C7 N3 C9 118.4(4) . . ? C8 N3 C9 119.9(4) . . ? C7 N4 C11 114.0(4) . . ? C11 N5 C13 119.0(3) . . ? C11 N5 C12 121.3(3) . . ? C13 N5 C12 119.6(3) . . ? C6 N6 C11 113.7(4) . . ? O2 C1 O1 123.9(5) . . ? O2 C1 C2 116.0(5) . . ? O1 C1 C2 120.0(4) . . ? N1 C2 C1 115.1(4) . . ? N1 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? N1 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? O4 C3 O3 123.5(4) . . ? O4 C3 C4 116.9(4) . . ? O3 C3 C4 119.6(4) . . ? N1 C4 C3 114.4(4) . . ? N1 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? O7 C5 O11 124.2(4) . 5_756 ? O7 C5 C12 118.9(4) . 8_755 ? O11 C5 C12 116.6(4) 5_756 8_755 ? N6 C6 N2 127.9(4) . . ? N6 C6 N1 116.4(4) . . ? N2 C6 N1 115.6(4) . . ? N2 C7 N4 126.8(4) . . ? N2 C7 N3 116.5(4) . . ? N4 C7 N3 116.8(4) . . ? N3 C8 C15 112.9(4) . 4_556 ? N3 C8 H8A 109.0 . . ? C15 C8 H8A 109.0 4_556 . ? N3 C8 H8B 109.0 . . ? C15 C8 H8B 109.0 4_556 . ? H8A C8 H8B 107.8 . . ? N3 C9 C10 114.6(4) . . ? N3 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? N3 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O8 C10 O12 122.6(4) . 4_556 ? O8 C10 C9 117.2(4) . . ? O12 C10 C9 120.2(4) 4_556 . ? N4 C11 N6 125.0(4) . . ? N4 C11 N5 118.2(4) . . ? N6 C11 N5 116.7(4) . . ? N5 C12 C5 115.3(3) . 8_765 ? N5 C12 H12A 108.4 . . ? C5 C12 H12A 108.4 8_765 . ? N5 C12 H12B 108.4 . . ? C5 C12 H12B 108.4 8_765 . ? H12A C12 H12B 107.5 . . ? N5 C13 C14 115.3(4) . . ? N5 C13 H13A 108.4 . . ? C14 C13 H13A 108.4 . . ? N5 C13 H13B 108.4 . . ? C14 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? O9 C14 O10 126.2(4) . . ? O9 C14 C13 121.1(4) . . ? O10 C14 C13 112.6(4) . . ? O14 C15 O13 122.5(4) . . ? O14 C15 C8 116.7(4) . 4_456 ? O13 C15 C8 120.7(4) . 4_456 ? 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 O3 Zn2 O1 C1 -28.9(5) . . . . ? O6 Zn2 O1 C1 153.0(3) . . . . ? O7 Zn2 O1 C1 60.1(3) . . . . ? O5 Zn2 O1 C1 -122.4(4) . . . . ? N1 Zn2 O1 C1 -26.3(3) . . . . ? O16 Zn3 O2 C1 164.6(4) 5_656 . . . ? O16 Zn3 O2 C1 -12.1(5) . . . . ? O15 Zn3 O2 C1 -99.6(4) . . . . ? O15 Zn3 O2 C1 84.0(4) 5_656 . . . ? O1 Zn2 O3 C3 32.1(5) . . . . ? O6 Zn2 O3 C3 -149.7(3) . . . . ? O7 Zn2 O3 C3 -57.2(3) . . . . ? O5 Zn2 O3 C3 122.9(3) . . . . ? N1 Zn2 O3 C3 29.5(3) . . . . ? O1 Zn2 O3 Na1 -130.9(2) . . . 6_656 ? O6 Zn2 O3 Na1 47.32(18) . . . 6_656 ? O7 Zn2 O3 Na1 139.80(18) . . . 6_656 ? O5 Zn2 O3 Na1 -40.10(17) . . . 6_656 ? N1 Zn2 O3 Na1 -133.51(17) . . . 6_656 ? O3 Zn2 O5 Na1 133.27(15) . . . . ? O1 Zn2 O5 Na1 -75.62(17) . . . . ? O6 Zn2 O5 Na1 35.86(16) . . . . ? N1 Zn2 O5 Na1 -150.52(15) . . . . ? O4 Na1 O5 Zn2 53.8(7) 1_455 . . . ? O14 Na1 O5 Zn2 10.61(17) 5_656 . . . ? O8 Na1 O5 Zn2 -173.61(15) 1_455 . . . ? O3 Na1 O5 Zn2 -85.33(16) 6_556 . . . ? O17 Na1 O5 Zn2 114.9(2) . . . . ? O3 Zn2 O7 C5 -151.2(5) . . . . ? O1 Zn2 O7 C5 57.6(5) . . . . ? O6 Zn2 O7 C5 -53.5(5) . . . . ? N1 Zn2 O7 C5 132.9(5) . . . . ? O12 Zn1 O10 C14 55.8(4) . . . . ? O13 Zn1 O10 C14 -166.7(4) . . . . ? O11 Zn1 O10 C14 -41.5(4) . . . . ? O12 Zn1 O11 C5 99.4(5) . . . 5_756 ? O13 Zn1 O11 C5 -30.7(5) . . . 5_756 ? O10 Zn1 O11 C5 -138.7(5) . . . 5_756 ? O13 Zn1 O12 C10 -49.4(5) . . . 4_456 ? O11 Zn1 O12 C10 -178.3(5) . . . 4_456 ? O10 Zn1 O12 C10 77.7(5) . . . 4_456 ? O12 Zn1 O13 C15 39.5(5) . . . . ? O11 Zn1 O13 C15 153.3(4) . . . . ? O10 Zn1 O13 C15 -96.9(4) . . . . ? O16 Zn3 O15 Zn3 -76.0(2) 5_656 . . 5_656 ? O16 Zn3 O15 Zn3 63.1(2) . . . 5_656 ? O2 Zn3 O15 Zn3 -173.83(16) . . . 5_656 ? O15 Zn3 O15 Zn3 0.0 5_656 . . 5_656 ? O16 Zn3 O16 Zn3 0.0 5_656 . . 5_656 ? O15 Zn3 O16 Zn3 -93.1(2) . . . 5_656 ? O2 Zn3 O16 Zn3 175.0(2) . . . 5_656 ? O15 Zn3 O16 Zn3 58.39(17) 5_656 . . 5_656 ? O3 Zn2 N1 C6 85.6(3) . . . . ? O1 Zn2 N1 C6 -93.1(3) . . . . ? O7 Zn2 N1 C6 175.6(3) . . . . ? O5 Zn2 N1 C6 -9.1(3) . . . . ? O3 Zn2 N1 C2 -153.7(3) . . . . ? O1 Zn2 N1 C2 27.6(2) . . . . ? O7 Zn2 N1 C2 -63.7(3) . . . . ? O5 Zn2 N1 C2 111.6(3) . . . . ? O3 Zn2 N1 C4 -33.4(2) . . . . ? O1 Zn2 N1 C4 147.9(3) . . . . ? O7 Zn2 N1 C4 56.6(2) . . . . ? O5 Zn2 N1 C4 -128.1(2) . . . . ? Zn3 O2 C1 O1 -7.5(6) . . . . ? Zn3 O2 C1 C2 174.0(3) . . . . ? Zn2 O1 C1 O2 -159.1(4) . . . . ? Zn2 O1 C1 C2 19.3(5) . . . . ? C6 N1 C2 C1 85.6(5) . . . . ? C4 N1 C2 C1 -129.3(4) . . . . ? Zn2 N1 C2 C1 -27.2(4) . . . . ? O2 C1 C2 N1 -170.0(4) . . . . ? O1 C1 C2 N1 11.5(6) . . . . ? Na1 O4 C3 O3 153.7(4) 1_655 . . . ? Na1 O4 C3 C4 -28.3(7) 1_655 . . . ? Zn2 O3 C3 O4 159.4(4) . . . . ? Na1 O3 C3 O4 -38.3(6) 6_656 . . . ? Zn2 O3 C3 C4 -18.5(5) . . . . ? Na1 O3 C3 C4 143.8(3) 6_656 . . . ? C6 N1 C4 C3 -76.1(5) . . . . ? C2 N1 C4 C3 138.7(4) . . . . ? Zn2 N1 C4 C3 34.7(4) . . . . ? O4 C3 C4 N1 163.2(4) . . . . ? O3 C3 C4 N1 -18.8(6) . . . . ? Zn2 O7 C5 O11 167.3(4) . . . 5_756 ? Zn2 O7 C5 C12 -19.7(8) . . . 8_755 ? C11 N6 C6 N2 2.5(6) . . . . ? C11 N6 C6 N1 -176.7(4) . . . . ? C7 N2 C6 N6 -0.4(6) . . . . ? C7 N2 C6 N1 178.9(4) . . . . ? C2 N1 C6 N6 -19.3(6) . . . . ? C4 N1 C6 N6 -165.4(4) . . . . ? Zn2 N1 C6 N6 89.7(4) . . . . ? C2 N1 C6 N2 161.3(4) . . . . ? C4 N1 C6 N2 15.2(5) . . . . ? Zn2 N1 C6 N2 -89.7(4) . . . . ? C6 N2 C7 N4 -2.5(6) . . . . ? C6 N2 C7 N3 175.8(4) . . . . ? C11 N4 C7 N2 2.8(6) . . . . ? C11 N4 C7 N3 -175.4(4) . . . . ? C8 N3 C7 N2 179.7(4) . . . . ? C9 N3 C7 N2 19.9(6) . . . . ? C8 N3 C7 N4 -1.8(6) . . . . ? C9 N3 C7 N4 -161.7(4) . . . . ? C7 N3 C8 C15 68.9(5) . . . 4_556 ? C9 N3 C8 C15 -131.6(4) . . . 4_556 ? C7 N3 C9 C10 -84.7(5) . . . . ? C8 N3 C9 C10 115.7(4) . . . . ? Na1 O8 C10 O12 52.1(6) 1_655 . . 4_556 ? Na1 O8 C10 C9 -130.3(4) 1_655 . . . ? N3 C9 C10 O8 163.8(4) . . . . ? N3 C9 C10 O12 -18.5(6) . . . 4_556 ? C7 N4 C11 N6 -0.3(6) . . . . ? C7 N4 C11 N5 179.9(4) . . . . ? C6 N6 C11 N4 -2.1(6) . . . . ? C6 N6 C11 N5 177.7(4) . . . . ? C13 N5 C11 N4 178.4(4) . . . . ? C12 N5 C11 N4 -5.4(6) . . . . ? C13 N5 C11 N6 -1.4(6) . . . . ? C12 N5 C11 N6 174.8(4) . . . . ? C11 N5 C12 C5 115.8(4) . . . 8_765 ? C13 N5 C12 C5 -68.0(5) . . . 8_765 ? C11 N5 C13 C14 80.7(5) . . . . ? C12 N5 C13 C14 -95.6(5) . . . . ? Zn1 O10 C14 O9 -19.5(7) . . . . ? Zn1 O10 C14 C13 162.2(3) . . . . ? N5 C13 C14 O9 18.1(6) . . . . ? N5 C13 C14 O10 -163.5(4) . . . . ? Na1 O14 C15 O13 87.6(5) 5_656 . . . ? Na1 O14 C15 C8 -89.6(5) 5_656 . . 4_456 ? Zn1 O13 C15 O14 169.4(3) . . . . ? Zn1 O13 C15 C8 -13.4(7) . . . 4_456 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.365 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 943142' ####################################################################### # # 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_solid1 _audit_creation_method 'SHELXTL-NT2000 ver.6.12' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 Cl N6 Na4 O14' _chemical_formula_sum 'C15 H13 Cl N6 Na4 O14' _chemical_formula_weight 628.72 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.559(3) _cell_length_b 10.857(3) _cell_length_c 11.426(3) _cell_angle_alpha 108.323(4) _cell_angle_beta 108.209(4) _cell_angle_gamma 93.566(4) _cell_volume 1162.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3636 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.40 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.484 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.177 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.936 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11032 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4106 _reflns_number_gt 3760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+6.2171P] 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 4106 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.2179 _refine_ls_wR_factor_gt 0.2139 _refine_ls_goodness_of_fit_ref 1.215 _refine_ls_restrained_S_all 1.215 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 Cl1 Cl 0.10685(16) 0.51981(17) 0.31107(18) 0.0399(5) Uani 1 1 d . . . Na1 Na 0.3319(2) 0.4486(2) 0.4590(2) 0.0232(5) Uani 1 1 d . . . Na2 Na 0.0000 0.5000 0.5000 0.0350(8) Uani 1 2 d S . . Na3 Na 0.0176(2) 0.2492(2) 0.2566(2) 0.0284(6) Uani 1 1 d . . . Na4 Na 0.2122(3) 0.0126(3) 0.3421(3) 0.0486(8) Uani 1 1 d . . . Na5 Na 0.0000 0.0000 0.0000 0.0258(7) Uani 1 2 d S . . O1 O 0.1983(4) 0.1477(4) 0.1899(4) 0.0317(10) Uani 1 1 d . . . O2 O 0.3868(4) 0.2944(4) 0.2849(4) 0.0243(9) Uani 1 1 d . . . O3 O -0.1461(5) -0.0162(4) 0.3310(4) 0.0319(10) Uani 1 1 d . . . O4 O 0.1884(5) 0.1504(4) 0.5429(4) 0.0378(11) Uani 1 1 d . . . O5 O 0.1542(4) 0.3266(4) 0.4893(4) 0.0335(10) Uani 1 1 d . . . O6 O 0.7712(4) 0.1728(4) 0.8279(4) 0.0340(10) Uani 1 1 d . . . O7 O 0.9140(4) 0.2002(4) 1.0271(4) 0.0334(10) Uani 1 1 d . . . O8 O 0.6108(5) 0.2511(4) 0.6684(4) 0.0387(12) Uani 1 1 d . . . H8 H 0.6696 0.2471 0.7332 0.058 Uiso 1 1 calc R . . O9 O 0.5273(4) 0.4070(4) 0.6014(4) 0.0289(10) Uani 1 1 d . . . O10 O -0.0443(5) 0.0081(4) 0.1966(4) 0.0346(11) Uani 1 1 d . . . O11 O 0.1663(4) 0.6817(4) 0.6652(4) 0.0304(10) Uani 1 1 d . . . O12 O 0.3656(4) 0.6356(4) 0.6570(4) 0.0310(10) Uani 1 1 d . . . O13 O 0.4499(7) 0.0778(7) 0.4210(6) 0.082(2) Uani 1 1 d . . . O14 O 0.1751(7) -0.1567(6) 0.4412(6) 0.0680(17) Uani 1 1 d . . . N1 N -0.2185(4) -0.2852(4) 0.1958(4) 0.0190(10) Uani 1 1 d . . . N2 N 0.4029(4) 0.7234(4) 0.9738(4) 0.0185(10) Uani 1 1 d . . . N3 N 0.6422(4) 0.7871(4) 1.0422(4) 0.0163(9) Uani 1 1 d . . . N4 N 0.4487(4) 0.3493(4) 0.8658(4) 0.0191(10) Uani 1 1 d . . . N5 N 0.6815(5) 0.4047(4) 0.9296(4) 0.0194(10) Uani 1 1 d . . . N6 N 0.4965(4) 0.8528(4) 0.8865(4) 0.0171(9) Uani 1 1 d . . . C1 C -0.0986(5) -0.0624(6) 0.2383(5) 0.0225(12) Uani 1 1 d . . . C2 C 0.8349(5) 0.2416(6) 0.9498(5) 0.0219(12) Uani 1 1 d . . . C3 C 0.1788(5) 0.2713(6) 0.5712(6) 0.0228(12) Uani 1 1 d . . . C4 C -0.1083(5) -0.2113(6) 0.1831(5) 0.0207(12) Uani 1 1 d . . . H4A H -0.1191 -0.2375 0.0907 0.025 Uiso 1 1 calc R . . H4B H -0.0239 -0.2340 0.2282 0.025 Uiso 1 1 calc R . . C5 C 0.2901(5) 0.7132(5) 0.7031(5) 0.0194(11) Uani 1 1 d . . . C6 C 0.3593(5) 0.8479(5) 0.8016(5) 0.0214(12) Uani 1 1 d . . . H6A H 0.3624 0.9079 0.7546 0.026 Uiso 1 1 calc R . . H6B H 0.3054 0.8789 0.8562 0.026 Uiso 1 1 calc R . . C7 C 0.6526(5) 0.7168(5) 1.1214(5) 0.0160(11) Uani 1 1 d . . . C8 C 0.6142(5) 0.9132(5) 0.8731(5) 0.0188(11) Uani 1 1 d . . . H8A H 0.6796 0.9613 0.9604 0.023 Uiso 1 1 calc R . . H8B H 0.5876 0.9767 0.8305 0.023 Uiso 1 1 calc R . . C9 C 0.5139(5) 0.7853(5) 0.9704(5) 0.0169(11) Uani 1 1 d . . . C10 C 0.1951(6) 0.3528(6) 0.7107(5) 0.0225(12) Uani 1 1 d . . . H14A H 0.2702 0.4252 0.7429 0.027 Uiso 1 1 calc R . . H14B H 0.1141 0.3908 0.7090 0.027 Uiso 1 1 calc R . . C11 C 0.3166(5) 0.1830(5) 0.2051(5) 0.0175(11) Uani 1 1 d . . . C12 C 0.5913(6) 0.3707(6) 0.6901(6) 0.0245(13) Uani 1 1 d . . . C13 C 0.6525(6) 0.4679(6) 0.8315(5) 0.0229(12) Uani 1 1 d . . . H22A H 0.7359 0.5200 0.8416 0.027 Uiso 1 1 calc R . . H22B H 0.5903 0.5277 0.8477 0.027 Uiso 1 1 calc R . . C14 C 0.8132(6) 0.3837(6) 0.9975(6) 0.0245(12) Uani 1 1 d . . . H40A H 0.8271 0.4108 1.0906 0.029 Uiso 1 1 calc R . . H40B H 0.8811 0.4398 0.9873 0.029 Uiso 1 1 calc R . . C15 C 0.5712(5) 0.3413(5) 0.9414(5) 0.0157(11) 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 Cl1 0.0305(8) 0.0448(10) 0.0516(11) 0.0228(8) 0.0173(7) 0.0105(7) Na1 0.0200(11) 0.0261(12) 0.0229(12) 0.0085(9) 0.0068(9) 0.0036(9) Na2 0.0341(19) 0.035(2) 0.0327(19) 0.0084(16) 0.0113(15) 0.0032(15) Na3 0.0252(12) 0.0290(13) 0.0254(12) 0.0051(10) 0.0062(10) 0.0040(10) Na4 0.0515(18) 0.0474(17) 0.0446(17) 0.0105(14) 0.0202(14) 0.0061(14) Na5 0.0280(17) 0.0257(17) 0.0234(16) 0.0064(13) 0.0105(13) 0.0064(13) O1 0.017(2) 0.030(2) 0.042(3) 0.004(2) 0.0121(19) 0.0026(17) O2 0.022(2) 0.020(2) 0.026(2) -0.0006(17) 0.0098(17) 0.0017(16) O3 0.046(3) 0.024(2) 0.031(2) 0.0093(18) 0.020(2) 0.0071(19) O4 0.063(3) 0.031(3) 0.027(2) 0.0117(19) 0.025(2) 0.011(2) O5 0.039(2) 0.038(3) 0.022(2) 0.0166(19) 0.0042(18) -0.006(2) O6 0.039(3) 0.033(2) 0.024(2) 0.0054(19) 0.0059(19) 0.015(2) O7 0.037(2) 0.035(2) 0.027(2) 0.014(2) 0.0046(19) 0.016(2) O8 0.058(3) 0.030(2) 0.021(2) 0.0072(19) 0.005(2) 0.016(2) O9 0.026(2) 0.034(2) 0.024(2) 0.0148(19) 0.0018(17) 0.0056(18) O10 0.037(2) 0.032(2) 0.042(3) 0.015(2) 0.024(2) 0.000(2) O11 0.016(2) 0.035(2) 0.030(2) 0.0015(19) 0.0063(17) 0.0018(17) O12 0.018(2) 0.028(2) 0.030(2) -0.0084(18) 0.0058(17) -0.0006(17) O13 0.082(5) 0.079(5) 0.058(4) 0.023(3) -0.007(3) -0.006(4) O14 0.092(5) 0.065(4) 0.053(4) 0.013(3) 0.040(3) 0.022(3) N1 0.020(2) 0.021(2) 0.016(2) 0.0072(19) 0.0057(18) 0.0040(19) N2 0.019(2) 0.021(2) 0.018(2) 0.0095(19) 0.0080(18) 0.0019(18) N3 0.015(2) 0.019(2) 0.013(2) 0.0057(18) 0.0031(17) 0.0031(18) N4 0.018(2) 0.021(2) 0.017(2) 0.0074(19) 0.0047(18) 0.0044(19) N5 0.023(2) 0.016(2) 0.015(2) 0.0053(18) 0.0006(18) 0.0045(19) N6 0.018(2) 0.021(2) 0.013(2) 0.0060(18) 0.0050(17) 0.0045(18) C1 0.015(3) 0.031(3) 0.017(3) 0.005(2) 0.004(2) 0.004(2) C2 0.019(3) 0.030(3) 0.022(3) 0.013(2) 0.011(2) 0.009(2) C3 0.018(3) 0.023(3) 0.027(3) 0.009(2) 0.009(2) -0.002(2) C4 0.014(3) 0.031(3) 0.022(3) 0.013(2) 0.008(2) 0.006(2) C5 0.018(3) 0.028(3) 0.014(3) 0.010(2) 0.005(2) 0.006(2) C6 0.021(3) 0.022(3) 0.024(3) 0.012(2) 0.008(2) 0.008(2) C7 0.018(3) 0.016(3) 0.014(3) 0.002(2) 0.007(2) 0.007(2) C8 0.025(3) 0.014(3) 0.014(3) 0.002(2) 0.005(2) 0.000(2) C9 0.021(3) 0.015(2) 0.011(2) -0.001(2) 0.005(2) 0.005(2) C10 0.019(3) 0.026(3) 0.024(3) 0.014(2) 0.004(2) 0.009(2) C11 0.020(3) 0.017(3) 0.017(3) 0.008(2) 0.007(2) 0.003(2) C12 0.023(3) 0.028(3) 0.025(3) 0.011(3) 0.009(2) 0.003(2) C13 0.025(3) 0.024(3) 0.025(3) 0.014(2) 0.010(2) 0.005(2) C14 0.018(3) 0.030(3) 0.021(3) 0.007(2) 0.003(2) -0.001(2) C15 0.016(3) 0.016(3) 0.011(2) 0.001(2) 0.004(2) 0.001(2) _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 Cl1 Na1 2.764(3) . ? Cl1 Na2 2.7863(18) . ? Cl1 Na3 2.836(3) . ? Na1 O9 2.365(4) . ? Na1 O5 2.405(5) . ? Na1 O2 2.417(4) . ? Na1 O12 2.426(4) . ? Na1 O9 2.486(5) 2_666 ? Na1 Na1 3.391(4) 2_666 ? Na2 O11 2.386(4) 2_566 ? Na2 O11 2.386(4) . ? Na2 O5 2.563(5) 2_566 ? Na2 O5 2.563(5) . ? Na2 Cl1 2.7863(18) 2_566 ? Na2 Na3 3.287(2) 2_566 ? Na2 Na1 3.731(2) 2_566 ? Na3 O7 2.369(5) 1_454 ? Na3 O5 2.430(5) . ? Na3 O11 2.444(5) 2_566 ? Na3 O1 2.466(5) . ? Na3 O10 2.475(5) . ? Na4 O13 2.362(8) . ? Na4 O6 2.377(5) 2_656 ? Na4 O4 2.412(5) . ? Na4 O14 2.513(7) . ? Na4 O1 2.581(6) . ? Na4 O10 2.687(6) . ? Na5 O7 2.375(4) 1_454 ? Na5 O7 2.375(4) 2_656 ? Na5 O10 2.410(4) . ? Na5 O10 2.410(4) 2 ? Na5 O1 2.494(4) . ? Na5 O1 2.494(4) 2 ? Na5 Na3 3.250(2) 2 ? Na5 Na4 3.804(3) 2 ? O1 C11 1.225(7) . ? O2 C11 1.271(6) . ? O3 C1 1.286(7) . ? O4 C3 1.267(7) . ? O5 C3 1.235(7) . ? O6 C2 1.284(7) . ? O6 Na4 2.377(5) 2_656 ? O7 C2 1.231(7) . ? O7 Na3 2.369(5) 1_656 ? O7 Na5 2.375(4) 1_656 ? O8 C12 1.286(7) . ? O8 H8 0.8200 . ? O9 C12 1.222(7) . ? O9 Na1 2.486(5) 2_666 ? O10 C1 1.220(7) . ? O11 C5 1.229(7) . ? O11 Na3 2.444(5) 2_566 ? O12 C5 1.300(7) . ? N1 C7 1.367(7) 1_444 ? N1 C4 1.442(7) . ? N1 C10 1.446(7) 2_556 ? N2 C9 1.332(7) . ? N2 C15 1.339(7) 2_667 ? N3 C7 1.340(7) . ? N3 C9 1.342(7) . ? N4 C7 1.322(7) 2_667 ? N4 C15 1.338(7) . ? N5 C15 1.380(7) . ? N5 C14 1.437(7) . ? N5 C13 1.455(7) . ? N6 C9 1.356(7) . ? N6 C8 1.442(7) . ? N6 C6 1.457(7) . ? C1 C4 1.523(8) . ? C2 C14 1.525(8) . ? C3 C10 1.509(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.502(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N4 1.322(7) 2_667 ? C7 N1 1.367(7) 1_666 ? C8 C11 1.530(7) 2_666 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 N1 1.446(7) 2_556 ? C10 H14A 0.9700 . ? C10 H14B 0.9700 . ? C11 C8 1.530(7) 2_666 ? C12 C13 1.528(8) . ? C13 H22A 0.9700 . ? C13 H22B 0.9700 . ? C14 H40A 0.9700 . ? C14 H40B 0.9700 . ? C15 N2 1.339(7) 2_667 ? 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 Na1 Cl1 Na2 84.47(7) . . ? Na1 Cl1 Na3 77.20(8) . . ? Na2 Cl1 Na3 71.54(6) . . ? O9 Na1 O5 101.48(17) . . ? O9 Na1 O2 84.89(15) . . ? O5 Na1 O2 105.79(16) . . ? O9 Na1 O12 81.06(16) . . ? O5 Na1 O12 92.93(16) . . ? O2 Na1 O12 158.52(16) . . ? O9 Na1 O9 91.33(15) . 2_666 ? O5 Na1 O9 167.08(17) . 2_666 ? O2 Na1 O9 76.77(15) . 2_666 ? O12 Na1 O9 87.35(16) . 2_666 ? O9 Na1 Cl1 174.61(15) . . ? O5 Na1 Cl1 79.41(13) . . ? O2 Na1 Cl1 100.03(12) . . ? O12 Na1 Cl1 93.60(13) . . ? O9 Na1 Cl1 87.68(12) 2_666 . ? O9 Na1 Na1 47.12(11) . 2_666 ? O5 Na1 Na1 148.57(16) . 2_666 ? O2 Na1 Na1 76.71(12) . 2_666 ? O12 Na1 Na1 81.82(12) . 2_666 ? O9 Na1 Na1 44.20(10) 2_666 2_666 ? Cl1 Na1 Na1 131.65(11) . 2_666 ? O11 Na2 O11 180.00(19) 2_566 . ? O11 Na2 O5 97.33(14) 2_566 2_566 ? O11 Na2 O5 82.67(14) . 2_566 ? O11 Na2 O5 82.67(14) 2_566 . ? O11 Na2 O5 97.33(14) . . ? O5 Na2 O5 180.000(1) 2_566 . ? O11 Na2 Cl1 90.88(11) 2_566 2_566 ? O11 Na2 Cl1 89.12(11) . 2_566 ? O5 Na2 Cl1 76.42(10) 2_566 2_566 ? O5 Na2 Cl1 103.58(10) . 2_566 ? O11 Na2 Cl1 89.12(11) 2_566 . ? O11 Na2 Cl1 90.88(11) . . ? O5 Na2 Cl1 103.58(10) 2_566 . ? O5 Na2 Cl1 76.42(10) . . ? Cl1 Na2 Cl1 180.0 2_566 . ? O11 Na2 Na3 132.15(10) 2_566 2_566 ? O11 Na2 Na3 47.85(10) . 2_566 ? O5 Na2 Na3 47.10(10) 2_566 2_566 ? O5 Na2 Na3 132.90(10) . 2_566 ? Cl1 Na2 Na3 54.94(6) 2_566 2_566 ? Cl1 Na2 Na3 125.06(6) . 2_566 ? O11 Na2 Na1 72.95(10) 2_566 2_566 ? O11 Na2 Na1 107.05(10) . 2_566 ? O5 Na2 Na1 39.76(10) 2_566 2_566 ? O5 Na2 Na1 140.24(10) . 2_566 ? Cl1 Na2 Na1 47.51(5) 2_566 2_566 ? Cl1 Na2 Na1 132.49(5) . 2_566 ? Na3 Na2 Na1 59.33(5) 2_566 2_566 ? O7 Na3 O5 169.70(19) 1_454 . ? O7 Na3 O11 101.46(17) 1_454 2_566 ? O5 Na3 O11 84.33(16) . 2_566 ? O7 Na3 O1 82.58(16) 1_454 . ? O5 Na3 O1 93.07(17) . . ? O11 Na3 O1 170.30(19) 2_566 . ? O7 Na3 O10 83.49(16) 1_454 . ? O5 Na3 O10 104.20(17) . . ? O11 Na3 O10 98.84(16) 2_566 . ? O1 Na3 O10 72.70(15) . . ? O7 Na3 Cl1 94.13(14) 1_454 . ? O5 Na3 Cl1 77.56(12) . . ? O11 Na3 Cl1 86.83(13) 2_566 . ? O1 Na3 Cl1 101.76(13) . . ? O10 Na3 Cl1 174.17(14) . . ? O13 Na4 O6 89.5(2) . 2_656 ? O13 Na4 O4 93.9(2) . . ? O6 Na4 O4 162.6(2) 2_656 . ? O13 Na4 O14 104.3(3) . . ? O6 Na4 O14 83.30(19) 2_656 . ? O4 Na4 O14 79.35(19) . . ? O13 Na4 O1 87.6(2) . . ? O6 Na4 O1 88.45(17) 2_656 . ? O4 Na4 O1 108.68(18) . . ? O14 Na4 O1 165.4(2) . . ? O13 Na4 O10 155.1(2) . . ? O6 Na4 O10 91.08(17) 2_656 . ? O4 Na4 O10 92.89(18) . . ? O14 Na4 O10 100.5(2) . . ? O1 Na4 O10 67.50(14) . . ? O7 Na5 O7 180.0(2) 1_454 2_656 ? O7 Na5 O10 84.79(15) 1_454 . ? O7 Na5 O10 95.21(15) 2_656 . ? O7 Na5 O10 95.21(15) 1_454 2 ? O7 Na5 O10 84.79(15) 2_656 2 ? O10 Na5 O10 180.0(3) . 2 ? O7 Na5 O1 81.87(14) 1_454 . ? O7 Na5 O1 98.13(14) 2_656 . ? O10 Na5 O1 73.31(15) . . ? O10 Na5 O1 106.69(15) 2 . ? O7 Na5 O1 98.13(14) 1_454 2 ? O7 Na5 O1 81.87(14) 2_656 2 ? O10 Na5 O1 106.69(15) . 2 ? O10 Na5 O1 73.31(15) 2 2 ? O1 Na5 O1 180.0(3) . 2 ? O7 Na5 Na3 133.31(11) 1_454 2 ? O7 Na5 Na3 46.69(11) 2_656 2 ? O10 Na5 Na3 130.84(11) . 2 ? O10 Na5 Na3 49.16(11) 2 2 ? O1 Na5 Na3 131.31(10) . 2 ? O1 Na5 Na3 48.69(10) 2 2 ? O7 Na5 Na4 73.19(11) 1_454 2 ? O7 Na5 Na4 106.81(11) 2_656 2 ? O10 Na5 Na4 135.40(12) . 2 ? O10 Na5 Na4 44.60(12) 2 2 ? O1 Na5 Na4 137.66(12) . 2 ? O1 Na5 Na4 42.34(12) 2 2 ? Na3 Na5 Na4 60.23(6) 2 2 ? C11 O1 Na3 137.1(4) . . ? C11 O1 Na5 134.0(4) . . ? Na3 O1 Na5 81.88(13) . . ? C11 O1 Na4 104.3(3) . . ? Na3 O1 Na4 90.04(16) . . ? Na5 O1 Na4 97.07(16) . . ? C11 O2 Na1 126.9(3) . . ? C3 O4 Na4 125.2(4) . . ? C3 O5 Na1 121.7(4) . . ? C3 O5 Na3 132.2(4) . . ? Na1 O5 Na3 92.56(16) . . ? C3 O5 Na2 120.3(4) . . ? Na1 O5 Na2 97.28(16) . . ? Na3 O5 Na2 82.30(14) . . ? C2 O6 Na4 140.2(4) . 2_656 ? C2 O7 Na3 139.9(4) . 1_656 ? C2 O7 Na5 132.9(4) . 1_656 ? Na3 O7 Na5 86.47(14) 1_656 1_656 ? C12 O8 H8 109.5 . . ? C12 O9 Na1 156.0(4) . . ? C12 O9 Na1 114.3(4) . 2_666 ? Na1 O9 Na1 88.67(15) . 2_666 ? C1 O10 Na5 140.0(4) . . ? C1 O10 Na3 134.8(4) . . ? Na5 O10 Na3 83.39(14) . . ? C1 O10 Na4 96.6(4) . . ? Na5 O10 Na4 96.36(16) . . ? Na3 O10 Na4 87.44(16) . . ? C5 O11 Na2 136.0(4) . . ? C5 O11 Na3 137.5(4) . 2_566 ? Na2 O11 Na3 85.77(14) . 2_566 ? C5 O12 Na1 136.0(3) . . ? C7 N1 C4 117.6(4) 1_444 . ? C7 N1 C10 120.6(4) 1_444 2_556 ? C4 N1 C10 121.7(4) . 2_556 ? C9 N2 C15 113.6(4) . 2_667 ? C7 N3 C9 113.6(4) . . ? C7 N4 C15 113.8(4) 2_667 . ? C15 N5 C14 117.4(4) . . ? C15 N5 C13 116.6(4) . . ? C14 N5 C13 125.0(5) . . ? C9 N6 C8 118.9(4) . . ? C9 N6 C6 118.5(4) . . ? C8 N6 C6 122.2(4) . . ? O10 C1 O3 122.7(5) . . ? O10 C1 C4 119.9(5) . . ? O3 C1 C4 117.4(5) . . ? O7 C2 O6 123.7(5) . . ? O7 C2 C14 119.4(5) . . ? O6 C2 C14 116.9(5) . . ? O5 C3 O4 123.2(5) . . ? O5 C3 C10 117.4(5) . . ? O4 C3 C10 119.4(5) . . ? N1 C4 C1 114.0(4) . . ? N1 C4 H4A 108.8 . . ? C1 C4 H4A 108.8 . . ? N1 C4 H4B 108.8 . . ? C1 C4 H4B 108.8 . . ? H4A C4 H4B 107.6 . . ? O11 C5 O12 122.4(5) . . ? O11 C5 C6 120.2(5) . . ? O12 C5 C6 117.3(5) . . ? N6 C6 C5 114.2(4) . . ? N6 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? N6 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? N4 C7 N3 126.5(5) 2_667 . ? N4 C7 N1 117.8(5) 2_667 1_666 ? N3 C7 N1 115.7(5) . 1_666 ? N6 C8 C11 114.8(4) . 2_666 ? N6 C8 H8A 108.6 . . ? C11 C8 H8A 108.6 2_666 . ? N6 C8 H8B 108.6 . . ? C11 C8 H8B 108.6 2_666 . ? H8A C8 H8B 107.5 . . ? N2 C9 N3 126.1(5) . . ? N2 C9 N6 117.3(5) . . ? N3 C9 N6 116.6(5) . . ? N1 C10 C3 116.7(5) 2_556 . ? N1 C10 H14A 108.1 2_556 . ? C3 C10 H14A 108.1 . . ? N1 C10 H14B 108.1 2_556 . ? C3 C10 H14B 108.1 . . ? H14A C10 H14B 107.3 . . ? O1 C11 O2 123.7(5) . . ? O1 C11 C8 118.5(5) . 2_666 ? O2 C11 C8 117.8(5) . 2_666 ? O9 C12 O8 121.8(5) . . ? O9 C12 C13 120.5(5) . . ? O8 C12 C13 117.7(5) . . ? N5 C13 C12 113.6(5) . . ? N5 C13 H22A 108.9 . . ? C12 C13 H22A 108.9 . . ? N5 C13 H22B 108.9 . . ? C12 C13 H22B 108.9 . . ? H22A C13 H22B 107.7 . . ? N5 C14 C2 114.4(5) . . ? N5 C14 H40A 108.7 . . ? C2 C14 H40A 108.7 . . ? N5 C14 H40B 108.7 . . ? C2 C14 H40B 108.7 . . ? H40A C14 H40B 107.6 . . ? N4 C15 N2 126.4(5) . 2_667 ? N4 C15 N5 116.7(5) . . ? N2 C15 N5 116.9(4) 2_667 . ? 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 Na2 Cl1 Na1 O5 33.57(12) . . . . ? Na3 Cl1 Na1 O5 -38.72(13) . . . . ? Na2 Cl1 Na1 O2 137.93(12) . . . . ? Na3 Cl1 Na1 O2 65.64(12) . . . . ? Na2 Cl1 Na1 O12 -58.74(12) . . . . ? Na3 Cl1 Na1 O12 -131.03(13) . . . . ? Na2 Cl1 Na1 O9 -145.94(11) . . . 2_666 ? Na3 Cl1 Na1 O9 141.77(12) . . . 2_666 ? Na2 Cl1 Na1 Na1 -140.99(14) . . . 2_666 ? Na3 Cl1 Na1 Na1 146.71(15) . . . 2_666 ? Na1 Cl1 Na2 O11 -114.32(12) . . . 2_566 ? Na3 Cl1 Na2 O11 -35.99(11) . . . 2_566 ? Na1 Cl1 Na2 O11 65.68(12) . . . . ? Na3 Cl1 Na2 O11 144.01(11) . . . . ? Na1 Cl1 Na2 O5 148.35(11) . . . 2_566 ? Na3 Cl1 Na2 O5 -133.32(11) . . . 2_566 ? Na1 Cl1 Na2 O5 -31.65(11) . . . . ? Na3 Cl1 Na2 O5 46.68(11) . . . . ? Na1 Cl1 Na2 Na3 101.67(8) . . . 2_566 ? Na3 Cl1 Na2 Na3 180.0 . . . 2_566 ? Na1 Cl1 Na2 Na1 180.0 . . . 2_566 ? Na3 Cl1 Na2 Na1 -101.67(8) . . . 2_566 ? Na1 Cl1 Na3 O7 -135.29(14) . . . 1_454 ? Na2 Cl1 Na3 O7 136.34(13) . . . 1_454 ? Na1 Cl1 Na3 O5 38.56(13) . . . . ? Na2 Cl1 Na3 O5 -49.81(12) . . . . ? Na1 Cl1 Na3 O11 123.44(13) . . . 2_566 ? Na2 Cl1 Na3 O11 35.07(11) . . . 2_566 ? Na1 Cl1 Na3 O1 -52.02(13) . . . . ? Na2 Cl1 Na3 O1 -140.39(13) . . . . ? O7 Na3 O1 C11 114.3(6) 1_454 . . . ? O5 Na3 O1 C11 -56.3(6) . . . . ? O10 Na3 O1 C11 -160.3(6) . . . . ? Cl1 Na3 O1 C11 21.6(6) . . . . ? O7 Na3 O1 Na5 -37.20(14) 1_454 . . . ? O5 Na3 O1 Na5 152.18(15) . . . . ? O10 Na3 O1 Na5 48.26(14) . . . . ? Cl1 Na3 O1 Na5 -129.89(11) . . . . ? O7 Na3 O1 Na4 -134.33(17) 1_454 . . . ? O5 Na3 O1 Na4 55.05(16) . . . . ? O10 Na3 O1 Na4 -48.87(15) . . . . ? Cl1 Na3 O1 Na4 132.97(12) . . . . ? O7 Na5 O1 C11 -116.0(5) 1_454 . . . ? O7 Na5 O1 C11 64.0(5) 2_656 . . . ? O10 Na5 O1 C11 157.1(5) . . . . ? O10 Na5 O1 C11 -22.9(5) 2 . . . ? Na3 Na5 O1 C11 26.9(6) 2 . . . ? Na4 Na5 O1 C11 -62.2(6) 2 . . . ? O7 Na5 O1 Na3 37.16(15) 1_454 . . . ? O7 Na5 O1 Na3 -142.84(15) 2_656 . . . ? O10 Na5 O1 Na3 -49.80(15) . . . . ? O10 Na5 O1 Na3 130.20(15) 2 . . . ? Na3 Na5 O1 Na3 180.0 2 . . . ? Na4 Na5 O1 Na3 90.97(16) 2 . . . ? O7 Na5 O1 Na4 126.19(17) 1_454 . . . ? O7 Na5 O1 Na4 -53.81(17) 2_656 . . . ? O10 Na5 O1 Na4 39.23(15) . . . . ? O10 Na5 O1 Na4 -140.77(15) 2 . . . ? Na3 Na5 O1 Na4 -90.97(16) 2 . . . ? Na4 Na5 O1 Na4 180.0 2 . . . ? O13 Na4 O1 C11 6.4(4) . . . . ? O6 Na4 O1 C11 -83.2(4) 2_656 . . . ? O4 Na4 O1 C11 99.7(4) . . . . ? O14 Na4 O1 C11 -138.7(8) . . . . ? O10 Na4 O1 C11 -175.0(4) . . . . ? O13 Na4 O1 Na3 -132.8(2) . . . . ? O6 Na4 O1 Na3 137.62(17) 2_656 . . . ? O4 Na4 O1 Na3 -39.5(2) . . . . ? O14 Na4 O1 Na3 82.1(8) . . . . ? O10 Na4 O1 Na3 45.80(14) . . . . ? O13 Na4 O1 Na5 145.4(2) . . . . ? O6 Na4 O1 Na5 55.80(17) 2_656 . . . ? O4 Na4 O1 Na5 -121.29(18) . . . . ? O14 Na4 O1 Na5 0.3(9) . . . . ? O10 Na4 O1 Na5 -36.02(13) . . . . ? O9 Na1 O2 C11 115.7(4) . . . . ? O5 Na1 O2 C11 15.2(5) . . . . ? O12 Na1 O2 C11 164.9(5) . . . . ? O9 Na1 O2 C11 -151.7(4) 2_666 . . . ? Cl1 Na1 O2 C11 -66.5(4) . . . . ? Na1 Na1 O2 C11 162.8(4) 2_666 . . . ? O13 Na4 O4 C3 85.0(5) . . . . ? O6 Na4 O4 C3 -174.0(6) 2_656 . . . ? O14 Na4 O4 C3 -171.2(5) . . . . ? O1 Na4 O4 C3 -3.8(5) . . . . ? O10 Na4 O4 C3 -71.0(5) . . . . ? O9 Na1 O5 C3 4.9(5) . . . . ? O2 Na1 O5 C3 92.8(5) . . . . ? O12 Na1 O5 C3 -76.5(5) . . . . ? O9 Na1 O5 C3 -167.4(7) 2_666 . . . ? Cl1 Na1 O5 C3 -169.6(5) . . . . ? Na1 Na1 O5 C3 2.6(6) 2_666 . . . ? O9 Na1 O5 Na3 -139.95(17) . . . . ? O2 Na1 O5 Na3 -52.08(19) . . . . ? O12 Na1 O5 Na3 138.59(17) . . . . ? O9 Na1 O5 Na3 47.7(8) 2_666 . . . ? Cl1 Na1 O5 Na3 45.46(13) . . . . ? Na1 Na1 O5 Na3 -142.3(2) 2_666 . . . ? O9 Na1 O5 Na2 137.49(15) . . . . ? O2 Na1 O5 Na2 -134.64(15) . . . . ? O12 Na1 O5 Na2 56.02(16) . . . . ? O9 Na1 O5 Na2 -34.9(8) 2_666 . . . ? Cl1 Na1 O5 Na2 -37.10(11) . . . . ? Na1 Na1 O5 Na2 135.1(3) 2_666 . . . ? O7 Na3 O5 C3 -146.3(9) 1_454 . . . ? O11 Na3 O5 C3 89.0(5) 2_566 . . . ? O1 Na3 O5 C3 -81.6(5) . . . . ? O10 Na3 O5 C3 -8.7(6) . . . . ? Cl1 Na3 O5 C3 177.0(5) . . . . ? O7 Na3 O5 Na1 -7.6(11) 1_454 . . . ? O11 Na3 O5 Na1 -132.36(18) 2_566 . . . ? O1 Na3 O5 Na1 57.01(18) . . . . ? O10 Na3 O5 Na1 129.93(16) . . . . ? Cl1 Na3 O5 Na1 -44.36(12) . . . . ? O7 Na3 O5 Na2 89.4(10) 1_454 . . . ? O11 Na3 O5 Na2 -35.35(13) 2_566 . . . ? O1 Na3 O5 Na2 154.01(14) . . . . ? O10 Na3 O5 Na2 -133.07(14) . . . . ? Cl1 Na3 O5 Na2 52.64(8) . . . . ? O11 Na2 O5 C3 -98.4(4) 2_566 . . . ? O11 Na2 O5 C3 81.6(4) . . . . ? Cl1 Na2 O5 C3 -9.3(4) 2_566 . . . ? Cl1 Na2 O5 C3 170.7(4) . . . . ? Na3 Na2 O5 C3 45.1(5) 2_566 . . . ? Na1 Na2 O5 C3 -46.6(5) 2_566 . . . ? O11 Na2 O5 Na1 128.10(17) 2_566 . . . ? O11 Na2 O5 Na1 -51.90(17) . . . . ? Cl1 Na2 O5 Na1 -142.77(11) 2_566 . . . ? Cl1 Na2 O5 Na1 37.23(11) . . . . ? Na3 Na2 O5 Na1 -88.38(16) 2_566 . . . ? Na1 Na2 O5 Na1 180.0 2_566 . . . ? O11 Na2 O5 Na3 36.48(14) 2_566 . . . ? O11 Na2 O5 Na3 -143.52(14) . . . . ? Cl1 Na2 O5 Na3 125.62(10) 2_566 . . . ? Cl1 Na2 O5 Na3 -54.38(10) . . . . ? Na3 Na2 O5 Na3 180.0 2_566 . . . ? Na1 Na2 O5 Na3 88.38(16) 2_566 . . . ? O5 Na1 O9 C12 -14.7(10) . . . . ? O2 Na1 O9 C12 -119.8(10) . . . . ? O12 Na1 O9 C12 76.5(10) . . . . ? O9 Na1 O9 C12 163.6(11) 2_666 . . . ? Na1 Na1 O9 C12 163.6(11) 2_666 . . . ? O5 Na1 O9 Na1 -178.30(17) . . . 2_666 ? O2 Na1 O9 Na1 76.59(14) . . . 2_666 ? O12 Na1 O9 Na1 -87.11(16) . . . 2_666 ? O9 Na1 O9 Na1 0.0 2_666 . . 2_666 ? O7 Na5 O10 C1 131.3(6) 1_454 . . . ? O7 Na5 O10 C1 -48.7(6) 2_656 . . . ? O1 Na5 O10 C1 -145.6(6) . . . . ? O1 Na5 O10 C1 34.4(6) 2 . . . ? Na3 Na5 O10 C1 -14.9(7) 2 . . . ? Na4 Na5 O10 C1 71.7(7) 2 . . . ? O7 Na5 O10 Na3 -33.74(15) 1_454 . . . ? O7 Na5 O10 Na3 146.26(15) 2_656 . . . ? O1 Na5 O10 Na3 49.32(14) . . . . ? O1 Na5 O10 Na3 -130.68(14) 2 . . . ? Na3 Na5 O10 Na3 180.0 2 . . . ? Na4 Na5 O10 Na3 -93.34(16) 2 . . . ? O7 Na5 O10 Na4 -120.40(17) 1_454 . . . ? O7 Na5 O10 Na4 59.60(17) 2_656 . . . ? O1 Na5 O10 Na4 -37.34(15) . . . . ? O1 Na5 O10 Na4 142.66(15) 2 . . . ? Na3 Na5 O10 Na4 93.34(16) 2 . . . ? Na4 Na5 O10 Na4 180.0 2 . . . ? O7 Na3 O10 C1 -132.6(6) 1_454 . . . ? O5 Na3 O10 C1 54.4(6) . . . . ? O11 Na3 O10 C1 -31.9(6) 2_566 . . . ? O1 Na3 O10 C1 143.2(6) . . . . ? O7 Na3 O10 Na5 33.92(15) 1_454 . . . ? O5 Na3 O10 Na5 -139.10(16) . . . . ? O11 Na3 O10 Na5 134.56(15) 2_566 . . . ? O1 Na3 O10 Na5 -50.31(14) . . . . ? O7 Na3 O10 Na4 130.63(16) 1_454 . . . ? O5 Na3 O10 Na4 -42.39(18) . . . . ? O11 Na3 O10 Na4 -128.73(15) 2_566 . . . ? O1 Na3 O10 Na4 46.41(15) . . . . ? O13 Na4 O10 C1 -177.2(6) . . . . ? O6 Na4 O10 C1 91.6(4) 2_656 . . . ? O4 Na4 O10 C1 -71.5(4) . . . . ? O14 Na4 O10 C1 8.2(4) . . . . ? O1 Na4 O10 C1 179.5(4) . . . . ? O13 Na4 O10 Na5 40.8(6) . . . . ? O6 Na4 O10 Na5 -50.46(18) 2_656 . . . ? O4 Na4 O10 Na5 146.45(17) . . . . ? O14 Na4 O10 Na5 -133.84(18) . . . . ? O1 Na4 O10 Na5 37.42(14) . . . . ? O13 Na4 O10 Na3 -42.3(6) . . . . ? O6 Na4 O10 Na3 -133.52(17) 2_656 . . . ? O4 Na4 O10 Na3 63.40(17) . . . . ? O14 Na4 O10 Na3 143.10(18) . . . . ? O1 Na4 O10 Na3 -45.64(14) . . . . ? O5 Na2 O11 C5 -153.1(6) 2_566 . . . ? O5 Na2 O11 C5 26.9(6) . . . . ? Cl1 Na2 O11 C5 130.4(5) 2_566 . . . ? Cl1 Na2 O11 C5 -49.6(5) . . . . ? Na3 Na2 O11 C5 170.9(6) 2_566 . . . ? Na1 Na2 O11 C5 175.1(5) 2_566 . . . ? O5 Na2 O11 Na3 35.97(14) 2_566 . . 2_566 ? O5 Na2 O11 Na3 -144.03(14) . . . 2_566 ? Cl1 Na2 O11 Na3 -40.45(12) 2_566 . . 2_566 ? Cl1 Na2 O11 Na3 139.55(12) . . . 2_566 ? Na1 Na2 O11 Na3 4.21(15) 2_566 . . 2_566 ? O9 Na1 O12 C5 -156.5(6) . . . . ? O5 Na1 O12 C5 -55.3(6) . . . . ? O2 Na1 O12 C5 153.8(5) . . . . ? O9 Na1 O12 C5 111.7(5) 2_666 . . . ? Cl1 Na1 O12 C5 24.2(6) . . . . ? Na1 Na1 O12 C5 155.8(6) 2_666 . . . ? Na5 O10 C1 O3 -154.7(4) . . . . ? Na3 O10 C1 O3 4.1(9) . . . . ? Na4 O10 C1 O3 97.1(5) . . . . ? Na5 O10 C1 C4 27.1(9) . . . . ? Na3 O10 C1 C4 -174.1(4) . . . . ? Na4 O10 C1 C4 -81.1(5) . . . . ? Na3 O7 C2 O6 -161.4(4) 1_656 . . . ? Na5 O7 C2 O6 4.8(9) 1_656 . . . ? Na3 O7 C2 C14 20.9(9) 1_656 . . . ? Na5 O7 C2 C14 -172.9(4) 1_656 . . . ? Na4 O6 C2 O7 -22.9(10) 2_656 . . . ? Na4 O6 C2 C14 154.8(5) 2_656 . . . ? Na1 O5 C3 O4 -95.8(6) . . . . ? Na3 O5 C3 O4 33.3(9) . . . . ? Na2 O5 C3 O4 142.0(5) . . . . ? Na1 O5 C3 C10 85.4(6) . . . . ? Na3 O5 C3 C10 -145.5(4) . . . . ? Na2 O5 C3 C10 -36.8(6) . . . . ? Na4 O4 C3 O5 14.5(8) . . . . ? Na4 O4 C3 C10 -166.7(4) . . . . ? C7 N1 C4 C1 68.7(6) 1_444 . . . ? C10 N1 C4 C1 -107.6(6) 2_556 . . . ? O10 C1 C4 N1 -155.1(5) . . . . ? O3 C1 C4 N1 26.6(7) . . . . ? Na2 O11 C5 O12 -5.3(9) . . . . ? Na3 O11 C5 O12 161.2(4) 2_566 . . . ? Na2 O11 C5 C6 171.8(4) . . . . ? Na3 O11 C5 C6 -21.7(8) 2_566 . . . ? Na1 O12 C5 O11 21.7(9) . . . . ? Na1 O12 C5 C6 -155.5(4) . . . . ? C9 N6 C6 C5 -64.5(6) . . . . ? C8 N6 C6 C5 107.9(5) . . . . ? O11 C5 C6 N6 150.1(5) . . . . ? O12 C5 C6 N6 -32.7(7) . . . . ? C9 N3 C7 N4 -0.7(7) . . . 2_667 ? C9 N3 C7 N1 179.5(4) . . . 1_666 ? C9 N6 C8 C11 74.1(6) . . . 2_666 ? C6 N6 C8 C11 -98.2(6) . . . 2_666 ? C15 N2 C9 N3 -0.1(7) 2_667 . . . ? C15 N2 C9 N6 179.7(4) 2_667 . . . ? C7 N3 C9 N2 0.9(7) . . . . ? C7 N3 C9 N6 -178.9(4) . . . . ? C8 N6 C9 N2 -175.6(4) . . . . ? C6 N6 C9 N2 -3.0(7) . . . . ? C8 N6 C9 N3 4.2(7) . . . . ? C6 N6 C9 N3 176.8(4) . . . . ? O5 C3 C10 N1 177.6(5) . . . 2_556 ? O4 C3 C10 N1 -1.2(8) . . . 2_556 ? Na3 O1 C11 O2 10.5(9) . . . . ? Na5 O1 C11 O2 149.4(4) . . . . ? Na4 O1 C11 O2 -95.6(5) . . . . ? Na3 O1 C11 C8 -171.3(4) . . . 2_666 ? Na5 O1 C11 C8 -32.4(7) . . . 2_666 ? Na4 O1 C11 C8 82.7(5) . . . 2_666 ? Na1 O2 C11 O1 13.7(8) . . . . ? Na1 O2 C11 C8 -164.6(3) . . . 2_666 ? Na1 O9 C12 O8 90.1(11) . . . . ? Na1 O9 C12 O8 -108.0(6) 2_666 . . . ? Na1 O9 C12 C13 -90.6(10) . . . . ? Na1 O9 C12 C13 71.3(6) 2_666 . . . ? C15 N5 C13 C12 -67.2(6) . . . . ? C14 N5 C13 C12 101.4(6) . . . . ? O9 C12 C13 N5 159.0(5) . . . . ? O8 C12 C13 N5 -21.6(7) . . . . ? C15 N5 C14 C2 63.5(6) . . . . ? C13 N5 C14 C2 -105.1(6) . . . . ? O7 C2 C14 N5 -151.1(5) . . . . ? O6 C2 C14 N5 31.1(7) . . . . ? C7 N4 C15 N2 -1.2(8) 2_667 . . 2_667 ? C7 N4 C15 N5 178.0(4) 2_667 . . . ? C14 N5 C15 N4 -172.4(5) . . . . ? C13 N5 C15 N4 -2.9(7) . . . . ? C14 N5 C15 N2 6.8(7) . . . 2_667 ? C13 N5 C15 N2 176.3(5) . . . 2_667 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.967 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 943175' ####################################################################### # # 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_Solid2 _audit_creation_method 'SHELXTL-NT2000 ver.6.12' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 Mg2 N6 O13 ' _chemical_formula_sum 'C15 H14 Mg2 N6 O13 ' _chemical_formula_weight 534.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3371(16) _cell_length_b 10.693(3) _cell_length_c 18.670(6) _cell_angle_alpha 80.696(5) _cell_angle_beta 84.700(5) _cell_angle_gamma 86.105(6) _cell_volume 1045.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2406 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.40 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.422 _exptl_crystal_size_mid 0.351 _exptl_crystal_size_min 0.295 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10121 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3693 _reflns_number_gt 3266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.7169P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3693 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.1703 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.211 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 Mg1 Mg 0.5663(3) 0.66549(15) 0.01494(9) 0.0410(4) Uani 1 1 d . . . Mg2 Mg 0.0236(3) -0.34216(18) 0.53575(10) 0.0522(5) Uani 1 1 d . . . O1 O 0.1861(5) 0.7211(3) -0.03853(15) 0.0308(7) Uani 1 1 d . . . O2 O 0.9545(5) 0.5918(3) 0.06479(15) 0.0339(7) Uani 1 1 d . . . O3 O 0.3527(6) 0.7337(3) 0.12515(18) 0.0433(8) Uani 1 1 d . . . O4 O 0.3170(5) 0.4762(3) 0.07432(14) 0.0287(6) Uani 1 1 d . . . O5 O 0.1946(5) -0.0700(3) 0.44733(16) 0.0342(7) Uani 1 1 d . . . O6 O 0.2504(7) -0.2655(3) 0.42359(17) 0.0437(8) Uani 1 1 d . . . O7 O 0.4015(6) -0.2923(3) 0.57908(17) 0.0395(8) Uani 1 1 d . . . O8 O -0.2963(5) -0.1580(3) 0.55592(15) 0.0323(7) Uani 1 1 d . . . O9 O -0.0665(6) -0.4876(3) 0.64993(18) 0.0467(9) Uani 1 1 d . . . O10 O -0.3949(7) -0.6090(3) 0.6764(2) 0.0533(10) Uani 1 1 d . . . O11 O -0.2550(6) -0.4333(3) 0.47005(18) 0.0448(8) Uani 1 1 d . . . O12 O 0.3452(6) 0.9267(3) 0.06575(16) 0.0344(7) Uani 1 1 d . . . O13 O 0.8363(5) 0.8453(3) -0.03796(15) 0.0293(7) Uani 1 1 d . . . N1 N 0.1855(6) 0.3866(3) 0.22056(16) 0.0217(7) Uani 1 1 d . . . N2 N 0.0603(6) 0.1972(3) 0.19682(16) 0.0224(7) Uani 1 1 d . . . N3 N -0.0276(6) 0.0077(3) 0.16747(16) 0.0223(7) Uani 1 1 d . . . N4 N 0.2625(6) 0.0039(3) 0.25281(16) 0.0234(7) Uani 1 1 d . . . N5 N 0.5476(6) 0.0186(3) 0.33717(16) 0.0225(7) Uani 1 1 d . . . N6 N 0.3832(6) 0.2041(3) 0.27597(16) 0.0227(7) Uani 1 1 d . . . C1 C 0.2562(8) 0.8395(4) 0.1182(2) 0.0271(9) Uani 1 1 d . . . C2 C 0.1092(7) 0.5081(3) 0.0996(2) 0.0225(8) Uani 1 1 d . . . C3 C 0.0010(7) 0.4545(3) 0.1755(2) 0.0246(9) Uani 1 1 d . . . H3A H -0.0768 0.5236 0.1990 0.030 Uiso 1 1 calc R . . H3B H -0.1297 0.3978 0.1715 0.030 Uiso 1 1 calc R . . C4 C 0.3597(7) 0.4613(4) 0.2480(2) 0.0253(9) Uani 1 1 d . . . H4A H 0.4136 0.5283 0.2092 0.030 Uiso 1 1 calc R . . H4B H 0.5075 0.4075 0.2610 0.030 Uiso 1 1 calc R . . C5 C 0.2100(7) 0.2576(3) 0.23162(18) 0.0203(8) Uani 1 1 d . . . C6 C 0.1051(7) 0.0706(3) 0.20782(19) 0.0201(8) Uani 1 1 d . . . C7 C -0.1946(7) 0.0821(4) 0.1173(2) 0.0241(8) Uani 1 1 d . . . H7A H -0.3250 0.1262 0.1450 0.029 Uiso 1 1 calc R . . H7B H -0.2762 0.0250 0.0925 0.029 Uiso 1 1 calc R . . C8 C 0.0284(8) -0.1269(3) 0.1667(2) 0.0269(9) Uani 1 1 d . . . H8A H -0.1171 -0.1622 0.1516 0.032 Uiso 1 1 calc R . . H8B H 0.0524 -0.1677 0.2161 0.032 Uiso 1 1 calc R . . C9 C 0.3929(7) 0.0767(3) 0.28665(18) 0.0199(8) Uani 1 1 d . . . C10 C 0.6824(7) 0.0979(4) 0.3751(2) 0.0260(9) Uani 1 1 d . . . H10A H 0.8003 0.1452 0.3400 0.031 Uiso 1 1 calc R . . H10B H 0.7802 0.0432 0.4102 0.031 Uiso 1 1 calc R . . C11 C 0.5388(7) -0.1166(4) 0.3617(2) 0.0258(9) Uani 1 1 d . . . H11A H 0.6901 -0.1467 0.3857 0.031 Uiso 1 1 calc R . . H11B H 0.5371 -0.1593 0.3197 0.031 Uiso 1 1 calc R . . C12 C 0.3076(8) -0.1518(4) 0.4143(2) 0.0264(9) Uani 1 1 d . . . C13 C -0.5213(8) -0.1905(4) 0.5855(2) 0.0267(9) Uani 1 1 d . . . C14 C -0.2546(8) -0.5200(4) 0.6872(2) 0.0290(9) Uani 1 1 d . . . C15 C 1.0607(7) 0.8214(3) -0.0608(2) 0.0224(8) Uani 1 1 d . . . H10 H -0.321(12) -0.651(6) 0.631(4) 0.09(2) Uiso 1 1 d . . . H12 H 0.261(13) 1.022(7) 0.059(4) 0.11(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mg1 0.0316(8) 0.0468(9) 0.0441(9) -0.0062(7) -0.0043(7) 0.0014(7) Mg2 0.0548(11) 0.0579(11) 0.0458(10) -0.0108(8) 0.0004(8) -0.0165(9) O1 0.0238(15) 0.0314(16) 0.0332(16) 0.0061(12) -0.0045(12) 0.0039(12) O2 0.0232(15) 0.0376(17) 0.0359(17) 0.0100(13) -0.0064(12) 0.0025(12) O3 0.054(2) 0.0238(16) 0.051(2) -0.0049(14) -0.0066(16) 0.0097(14) O4 0.0255(15) 0.0320(15) 0.0264(15) -0.0036(12) 0.0031(12) 0.0049(12) O5 0.0349(17) 0.0300(16) 0.0372(17) -0.0078(13) 0.0058(13) -0.0050(13) O6 0.071(2) 0.0263(16) 0.0355(17) -0.0100(13) 0.0062(16) -0.0170(15) O7 0.0457(19) 0.0290(17) 0.0479(19) -0.0109(14) -0.0106(15) -0.0099(14) O8 0.0303(16) 0.0324(16) 0.0338(16) -0.0075(13) 0.0037(13) -0.0027(12) O9 0.047(2) 0.056(2) 0.0414(19) -0.0225(16) 0.0115(16) -0.0169(17) O10 0.063(2) 0.048(2) 0.057(2) -0.0317(18) 0.0102(18) -0.0264(18) O11 0.0400(18) 0.0415(19) 0.055(2) -0.0130(16) -0.0083(16) -0.0025(15) O12 0.0359(17) 0.0271(16) 0.0380(17) -0.0007(13) 0.0022(13) -0.0023(13) O13 0.0241(15) 0.0279(15) 0.0317(15) 0.0044(12) 0.0010(12) 0.0021(12) N1 0.0282(17) 0.0170(15) 0.0201(16) -0.0009(12) -0.0058(13) -0.0019(13) N2 0.0277(18) 0.0174(16) 0.0224(17) -0.0025(13) -0.0058(14) 0.0001(13) N3 0.0264(17) 0.0201(16) 0.0200(16) -0.0016(13) -0.0025(13) -0.0015(13) N4 0.0303(18) 0.0177(16) 0.0223(17) -0.0012(13) -0.0071(14) 0.0000(13) N5 0.0264(17) 0.0226(17) 0.0176(16) 0.0005(13) -0.0064(13) 0.0022(13) N6 0.0284(17) 0.0182(16) 0.0216(16) -0.0004(13) -0.0062(14) -0.0024(13) C1 0.033(2) 0.023(2) 0.028(2) -0.0043(17) -0.0118(17) -0.0042(17) C2 0.024(2) 0.0207(19) 0.024(2) -0.0050(16) -0.0031(16) 0.0021(16) C3 0.027(2) 0.0183(19) 0.028(2) -0.0036(16) -0.0007(17) 0.0036(16) C4 0.029(2) 0.0196(19) 0.026(2) 0.0000(16) 0.0014(17) -0.0064(16) C5 0.026(2) 0.0196(18) 0.0130(17) 0.0009(14) 0.0051(15) -0.0032(15) C6 0.0236(19) 0.0202(19) 0.0158(18) -0.0027(15) 0.0024(15) -0.0026(15) C7 0.021(2) 0.029(2) 0.023(2) -0.0042(16) -0.0046(16) -0.0037(16) C8 0.037(2) 0.0181(19) 0.026(2) 0.0000(16) -0.0057(17) -0.0084(17) C9 0.025(2) 0.0211(19) 0.0129(17) -0.0032(15) 0.0033(15) -0.0023(15) C10 0.021(2) 0.034(2) 0.022(2) 0.0001(17) -0.0067(16) -0.0010(17) C11 0.030(2) 0.022(2) 0.024(2) 0.0002(16) -0.0065(16) 0.0078(16) C12 0.036(2) 0.023(2) 0.0194(19) 0.0000(16) -0.0090(17) 0.0002(17) C13 0.034(2) 0.027(2) 0.020(2) -0.0019(16) -0.0092(17) -0.0019(18) C14 0.035(2) 0.023(2) 0.030(2) -0.0036(17) -0.0011(19) -0.0069(18) C15 0.024(2) 0.0210(19) 0.0237(19) -0.0044(16) -0.0062(16) -0.0043(16) _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 Mg1 O1 2.342(3) . ? Mg1 O2 2.383(3) . ? Mg1 O4 2.441(3) 2_665 ? Mg1 O3 2.450(4) . ? Mg1 O4 2.542(3) . ? Mg2 O7 2.365(3) . ? Mg2 O6 2.373(4) . ? Mg2 O9 2.456(4) . ? Mg2 O8 2.569(3) . ? Mg2 O11 2.638(4) 2_546 ? O1 C15 1.258(5) 1_455 ? O2 C2 1.310(4) 1_655 ? O3 C1 1.204(5) . ? O4 C2 1.214(4) . ? O4 Mg1 2.441(3) 2_665 ? O5 C12 1.243(5) . ? O6 C12 1.254(5) . ? O7 C13 1.217(5) 1_655 ? O8 C13 1.319(5) . ? O9 C14 1.205(5) . ? O10 C14 1.302(5) . ? O10 H10 1.05(7) . ? O11 Mg2 2.638(4) 2_546 ? O12 C1 1.316(5) . ? O12 H12 1.08(7) . ? O13 C15 1.257(4) . ? N1 C5 1.360(5) . ? N1 C3 1.436(5) . ? N1 C4 1.444(5) . ? N2 C5 1.334(5) . ? N2 C6 1.344(5) . ? N3 C6 1.360(5) . ? N3 C8 1.452(5) . ? N3 C7 1.457(5) . ? N4 C6 1.332(5) . ? N4 C9 1.343(5) . ? N5 C9 1.357(5) . ? N5 C11 1.447(5) . ? N5 C10 1.454(5) . ? N6 C5 1.335(5) . ? N6 C9 1.342(5) . ? C1 C8 1.507(6) 1_565 ? C2 O2 1.310(4) 1_455 ? C2 C3 1.518(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C14 1.498(6) 2_556 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C7 C15 1.515(5) 2_665 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C1 1.507(6) 1_545 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C13 1.504(6) 2_556 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.533(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 O7 1.217(5) 1_455 ? C13 C10 1.504(6) 2_556 ? C14 C4 1.498(6) 2_556 ? C15 O1 1.258(5) 1_655 ? C15 C7 1.515(5) 2_665 ? 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 Mg1 O2 174.88(13) . . ? O1 Mg1 O4 89.28(11) . 2_665 ? O2 Mg1 O4 86.00(11) . 2_665 ? O1 Mg1 O3 86.54(12) . . ? O2 Mg1 O3 97.03(12) . . ? O4 Mg1 O3 156.92(12) 2_665 . ? O1 Mg1 O4 80.70(10) . . ? O2 Mg1 O4 96.56(11) . . ? O4 Mg1 O4 80.87(11) 2_665 . ? O3 Mg1 O4 76.06(11) . . ? O7 Mg2 O6 80.08(13) . . ? O7 Mg2 O9 89.65(13) . . ? O6 Mg2 O9 156.23(15) . . ? O7 Mg2 O8 105.73(12) . . ? O6 Mg2 O8 103.44(12) . . ? O9 Mg2 O8 99.96(12) . . ? O7 Mg2 O11 84.61(12) . 2_546 ? O6 Mg2 O11 88.44(12) . 2_546 ? O9 Mg2 O11 69.16(12) . 2_546 ? O8 Mg2 O11 165.30(12) . 2_546 ? C15 O1 Mg1 137.3(3) 1_455 . ? C2 O2 Mg1 155.0(3) 1_655 . ? C1 O3 Mg1 116.4(3) . . ? C2 O4 Mg1 129.2(3) . 2_665 ? C2 O4 Mg1 112.2(2) . . ? Mg1 O4 Mg1 99.13(11) 2_665 . ? C12 O6 Mg2 116.6(3) . . ? C13 O7 Mg2 130.7(3) 1_655 . ? C13 O8 Mg2 115.9(2) . . ? C14 O9 Mg2 135.2(3) . . ? C14 O10 H10 111(4) . . ? C1 O12 H12 120(4) . . ? C5 N1 C3 121.6(3) . . ? C5 N1 C4 121.2(3) . . ? C3 N1 C4 117.0(3) . . ? C5 N2 C6 113.1(3) . . ? C6 N3 C8 119.7(3) . . ? C6 N3 C7 118.1(3) . . ? C8 N3 C7 121.5(3) . . ? C6 N4 C9 113.2(3) . . ? C9 N5 C11 119.8(3) . . ? C9 N5 C10 118.0(3) . . ? C11 N5 C10 121.1(3) . . ? C5 N6 C9 113.9(3) . . ? O3 C1 O12 119.7(4) . . ? O3 C1 C8 121.2(4) . 1_565 ? O12 C1 C8 119.1(3) . 1_565 ? O4 C2 O2 124.1(3) . 1_455 ? O4 C2 C3 123.2(3) . . ? O2 C2 C3 112.8(3) 1_455 . ? N1 C3 C2 113.5(3) . . ? N1 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? N1 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? N1 C4 C14 114.4(3) . 2_556 ? N1 C4 H4A 108.7 . . ? C14 C4 H4A 108.7 2_556 . ? N1 C4 H4B 108.7 . . ? C14 C4 H4B 108.7 2_556 . ? H4A C4 H4B 107.6 . . ? N2 C5 N6 126.5(3) . . ? N2 C5 N1 116.9(3) . . ? N6 C5 N1 116.6(3) . . ? N4 C6 N2 127.0(3) . . ? N4 C6 N3 118.7(3) . . ? N2 C6 N3 114.3(3) . . ? N3 C7 C15 113.5(3) . 2_665 ? N3 C7 H7A 108.9 . . ? C15 C7 H7A 108.9 2_665 . ? N3 C7 H7B 108.9 . . ? C15 C7 H7B 108.9 2_665 . ? H7A C7 H7B 107.7 . . ? N3 C8 C1 115.8(3) . 1_545 ? N3 C8 H8A 108.3 . . ? C1 C8 H8A 108.3 1_545 . ? N3 C8 H8B 108.3 . . ? C1 C8 H8B 108.3 1_545 . ? H8A C8 H8B 107.4 . . ? N6 C9 N4 126.0(3) . . ? N6 C9 N5 115.7(3) . . ? N4 C9 N5 118.3(3) . . ? N5 C10 C13 115.7(3) . 2_556 ? N5 C10 H10A 108.4 . . ? C13 C10 H10A 108.4 2_556 . ? N5 C10 H10B 108.4 . . ? C13 C10 H10B 108.4 2_556 . ? H10A C10 H10B 107.4 . . ? N5 C11 C12 112.8(3) . . ? N5 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N5 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? O5 C12 O6 123.7(4) . . ? O5 C12 C11 119.5(3) . . ? O6 C12 C11 116.7(4) . . ? O7 C13 O8 120.2(4) 1_455 . ? O7 C13 C10 121.0(4) 1_455 2_556 ? O8 C13 C10 118.8(3) . 2_556 ? O9 C14 O10 124.9(4) . . ? O9 C14 C4 124.1(4) . 2_556 ? O10 C14 C4 111.0(4) . 2_556 ? O13 C15 O1 123.6(3) . 1_655 ? O13 C15 C7 119.7(3) . 2_665 ? O1 C15 C7 116.7(3) 1_655 2_665 ? 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 Mg1 O1 C15 -131.2(4) 2_665 . . 1_455 ? O3 Mg1 O1 C15 71.5(4) . . . 1_455 ? O4 Mg1 O1 C15 147.9(4) . . . 1_455 ? O4 Mg1 O2 C2 -70.3(6) 2_665 . . 1_655 ? O3 Mg1 O2 C2 86.8(6) . . . 1_655 ? O4 Mg1 O2 C2 10.1(6) . . . 1_655 ? O1 Mg1 O3 C1 -54.3(3) . . . . ? O2 Mg1 O3 C1 129.4(3) . . . . ? O4 Mg1 O3 C1 -134.2(3) 2_665 . . . ? O4 Mg1 O3 C1 -135.5(3) . . . . ? O1 Mg1 O4 C2 -48.5(3) . . . . ? O2 Mg1 O4 C2 135.9(3) . . . . ? O4 Mg1 O4 C2 -139.3(3) 2_665 . . . ? O3 Mg1 O4 C2 40.2(3) . . . . ? O1 Mg1 O4 Mg1 90.77(11) . . . 2_665 ? O2 Mg1 O4 Mg1 -84.86(12) . . . 2_665 ? O4 Mg1 O4 Mg1 0.0 2_665 . . 2_665 ? O3 Mg1 O4 Mg1 179.49(13) . . . 2_665 ? O7 Mg2 O6 C12 -62.5(3) . . . . ? O9 Mg2 O6 C12 -128.1(4) . . . . ? O8 Mg2 O6 C12 41.5(3) . . . . ? O11 Mg2 O6 C12 -147.3(3) 2_546 . . . ? O6 Mg2 O7 C13 76.3(4) . . . 1_655 ? O9 Mg2 O7 C13 -125.2(4) . . . 1_655 ? O8 Mg2 O7 C13 -24.9(4) . . . 1_655 ? O11 Mg2 O7 C13 165.7(4) 2_546 . . 1_655 ? O7 Mg2 O8 C13 -133.7(3) . . . . ? O6 Mg2 O8 C13 143.0(3) . . . . ? O9 Mg2 O8 C13 -41.3(3) . . . . ? O11 Mg2 O8 C13 -0.2(6) 2_546 . . . ? O7 Mg2 O9 C14 146.3(4) . . . . ? O6 Mg2 O9 C14 -149.8(4) . . . . ? O8 Mg2 O9 C14 40.4(4) . . . . ? O11 Mg2 O9 C14 -129.3(4) 2_546 . . . ? Mg1 O3 C1 O12 -26.7(5) . . . . ? Mg1 O3 C1 C8 151.0(3) . . . 1_565 ? Mg1 O4 C2 O2 -76.6(5) 2_665 . . 1_455 ? Mg1 O4 C2 O2 47.1(4) . . . 1_455 ? Mg1 O4 C2 C3 103.4(4) 2_665 . . . ? Mg1 O4 C2 C3 -132.9(3) . . . . ? C5 N1 C3 C2 -100.6(4) . . . . ? C4 N1 C3 C2 73.7(4) . . . . ? O4 C2 C3 N1 13.9(5) . . . . ? O2 C2 C3 N1 -166.0(3) 1_455 . . . ? C5 N1 C4 C14 -106.1(4) . . . 2_556 ? C3 N1 C4 C14 79.6(4) . . . 2_556 ? C6 N2 C5 N6 -2.6(5) . . . . ? C6 N2 C5 N1 176.9(3) . . . . ? C9 N6 C5 N2 -2.6(5) . . . . ? C9 N6 C5 N1 177.9(3) . . . . ? C3 N1 C5 N2 2.1(5) . . . . ? C4 N1 C5 N2 -171.9(3) . . . . ? C3 N1 C5 N6 -178.3(3) . . . . ? C4 N1 C5 N6 7.7(5) . . . . ? C9 N4 C6 N2 -3.2(5) . . . . ? C9 N4 C6 N3 176.6(3) . . . . ? C5 N2 C6 N4 5.8(5) . . . . ? C5 N2 C6 N3 -173.9(3) . . . . ? C8 N3 C6 N4 -8.2(5) . . . . ? C7 N3 C6 N4 -178.6(3) . . . . ? C8 N3 C6 N2 171.6(3) . . . . ? C7 N3 C6 N2 1.2(5) . . . . ? C6 N3 C7 C15 58.7(4) . . . 2_665 ? C8 N3 C7 C15 -111.6(4) . . . 2_665 ? C6 N3 C8 C1 -79.2(4) . . . 1_545 ? C7 N3 C8 C1 90.9(4) . . . 1_545 ? C5 N6 C9 N4 5.7(5) . . . . ? C5 N6 C9 N5 -173.4(3) . . . . ? C6 N4 C9 N6 -3.1(5) . . . . ? C6 N4 C9 N5 176.0(3) . . . . ? C11 N5 C9 N6 169.4(3) . . . . ? C10 N5 C9 N6 1.0(5) . . . . ? C11 N5 C9 N4 -9.8(5) . . . . ? C10 N5 C9 N4 -178.2(3) . . . . ? C9 N5 C10 C13 56.4(4) . . . 2_556 ? C11 N5 C10 C13 -111.8(4) . . . 2_556 ? C9 N5 C11 C12 -75.5(4) . . . . ? C10 N5 C11 C12 92.6(4) . . . . ? Mg2 O6 C12 O5 -22.5(5) . . . . ? Mg2 O6 C12 C11 154.4(3) . . . . ? N5 C11 C12 O5 -20.5(5) . . . . ? N5 C11 C12 O6 162.4(3) . . . . ? Mg2 O8 C13 O7 -25.2(5) . . . 1_455 ? Mg2 O8 C13 C10 156.8(3) . . . 2_556 ? Mg2 O9 C14 O10 84.0(6) . . . . ? Mg2 O9 C14 C4 -95.2(5) . . . 2_556 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.588 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 943176' ####################################################################### # # 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_Solid3a _audit_creation_method 'SHELXTL-NT2000 ver.6.12' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 Cu2 N6 O18' _chemical_formula_sum 'C15 H14 Cu2 N6 O18' _chemical_formula_weight 693.42 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' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_hall '-C 2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.799(4) _cell_length_b 10.812(2) _cell_length_c 10.723(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.793(3) _cell_angle_gamma 90.00 _cell_volume 2487.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2549 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 25.31 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.529 _exptl_crystal_size_mid 0.321 _exptl_crystal_size_min 0.181 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.503 _exptl_absorpt_correction_T_max 0.721 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11483 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2190 _reflns_number_gt 1892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+5.9220P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2190 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 Cu1 Cu 0.70874(2) 0.63231(4) 0.80312(5) 0.0285(2) Uani 1 1 d . . . O1 O 0.41610(17) 1.3667(3) 0.6824(4) 0.0509(9) Uani 1 1 d . . . O2 O 0.36288(14) 1.1966(3) 0.6713(3) 0.0369(7) Uani 1 1 d . . . O3 O 0.31786(14) 0.9918(3) 0.5404(3) 0.0385(7) Uani 1 1 d . . . O4 O 0.29464(13) 0.9110(3) 0.3385(3) 0.0379(7) Uani 1 1 d . . . O5 O 0.62292(13) 0.6729(3) 0.7780(3) 0.0366(7) Uani 1 1 d . . . O6 O 0.64823(16) 0.6117(3) 0.9858(3) 0.0491(9) Uani 1 1 d . . . O7 O 0.73529(16) 0.8073(3) 0.8506(4) 0.0497(9) Uani 1 1 d . . . O8 O 0.7077(2) 0.6508(5) 0.5885(4) 0.0893(17) Uani 1 1 d . . . O9 O 0.6846(2) 0.4555(3) 0.7707(6) 0.0924(17) Uani 1 1 d . . . N1 N 0.43194(14) 1.0754(3) 0.5367(3) 0.0253(7) Uani 1 1 d . . . N2 N 0.5000 1.0777(4) 0.7500 0.0236(10) Uani 1 2 d S . . N3 N 0.46347(15) 0.8867(3) 0.6387(3) 0.0267(8) Uani 1 1 d . . . N4 N 0.5000 0.7051(4) 0.7500 0.0306(11) Uani 1 2 d S . . C1 C 0.40404(19) 1.2631(4) 0.6393(4) 0.0317(9) Uani 1 1 d . . . C2 C 0.43389(18) 1.2085(4) 0.5448(4) 0.0277(9) Uani 1 1 d . . . H2A H 0.4130 1.2420 0.4570 0.033 Uiso 1 1 calc R . . H2B H 0.4771 1.2349 0.5725 0.033 Uiso 1 1 calc R . . C3 C 0.32956(18) 0.9684(4) 0.4370(4) 0.0280(9) Uani 1 1 d . . . C4 C 0.39047(18) 1.0118(4) 0.4218(4) 0.0291(9) Uani 1 1 d . . . H4A H 0.4121 0.9405 0.4034 0.035 Uiso 1 1 calc R . . H4B H 0.3808 1.0667 0.3460 0.035 Uiso 1 1 calc R . . C5 C 0.46673(16) 1.0093(3) 0.6459(4) 0.0219(8) Uani 1 1 d . . . C6 C 0.5000 0.8303(5) 0.7500 0.0250(12) Uani 1 2 d S . . C7 C 0.54059(19) 0.6397(4) 0.8650(5) 0.0329(10) Uani 1 1 d . . . H7A H 0.5274 0.5541 0.8600 0.039 Uiso 1 1 calc R . . H7B H 0.5358 0.6754 0.9440 0.039 Uiso 1 1 calc R . . C8 C 0.60876(19) 0.6435(4) 0.8784(4) 0.0302(9) Uani 1 1 d . . . H2 H 0.357(2) 1.128(4) 0.633(4) 0.027(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0239(3) 0.0319(3) 0.0323(3) 0.0060(2) 0.0126(2) 0.0050(2) O1 0.057(2) 0.0297(18) 0.074(2) -0.0105(16) 0.0324(19) -0.0039(15) O2 0.0388(18) 0.0328(18) 0.0476(19) 0.0013(15) 0.0257(15) -0.0014(14) O3 0.0396(17) 0.0447(18) 0.0364(17) -0.0071(14) 0.0198(14) -0.0172(14) O4 0.0254(15) 0.0482(18) 0.0405(17) -0.0178(15) 0.0117(14) -0.0130(14) O5 0.0276(15) 0.0485(18) 0.0373(17) 0.0074(14) 0.0157(13) 0.0082(14) O6 0.0362(18) 0.066(2) 0.0423(19) 0.0118(16) 0.0101(15) 0.0042(16) O7 0.047(2) 0.0370(18) 0.069(2) -0.0078(17) 0.0245(18) 0.0024(15) O8 0.076(3) 0.155(5) 0.033(2) 0.015(2) 0.014(2) 0.065(3) O9 0.084(3) 0.036(2) 0.199(5) -0.025(3) 0.102(4) -0.014(2) N1 0.0217(17) 0.0281(18) 0.0250(17) 0.0022(14) 0.0066(13) -0.0018(13) N2 0.019(2) 0.021(2) 0.031(2) 0.000 0.0080(19) 0.000 N3 0.0234(17) 0.0220(17) 0.0355(19) -0.0032(14) 0.0110(15) -0.0020(13) N4 0.016(2) 0.017(2) 0.055(3) 0.000 0.006(2) 0.000 C1 0.030(2) 0.027(2) 0.038(2) 0.0097(18) 0.0107(18) 0.0028(18) C2 0.026(2) 0.028(2) 0.031(2) 0.0068(17) 0.0107(17) -0.0014(16) C3 0.026(2) 0.028(2) 0.028(2) 0.0001(17) 0.0064(17) -0.0054(17) C4 0.025(2) 0.038(2) 0.0241(19) -0.0015(17) 0.0073(16) -0.0051(18) C5 0.0143(17) 0.023(2) 0.0287(19) -0.0020(15) 0.0083(15) -0.0027(15) C6 0.017(3) 0.024(3) 0.038(3) 0.000 0.014(2) 0.000 C7 0.027(2) 0.023(2) 0.052(3) 0.0068(18) 0.018(2) 0.0017(17) C8 0.027(2) 0.026(2) 0.037(2) 0.0024(18) 0.0108(18) 0.0046(17) _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 Cu1 O4 1.922(3) 8_566 ? Cu1 O5 1.933(3) . ? Cu1 O9 1.988(4) . ? Cu1 O7 1.999(3) . ? Cu1 O8 2.302(4) . ? O1 C1 1.207(5) . ? O2 C1 1.316(5) . ? O2 H2 0.83(4) . ? O3 C3 1.251(5) . ? O4 C3 1.252(5) . ? O4 Cu1 1.922(3) 8_465 ? O5 C8 1.265(5) . ? O6 C8 1.246(5) . ? N1 C5 1.371(5) . ? N1 C2 1.442(5) . ? N1 C4 1.448(5) . ? N2 C5 1.339(4) 2_656 ? N2 C5 1.339(4) . ? N3 C5 1.329(5) . ? N3 C6 1.348(4) . ? N4 C6 1.354(7) . ? N4 C7 1.450(5) 2_656 ? N4 C7 1.450(5) . ? C1 C2 1.519(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.526(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 N3 1.348(4) 2_656 ? C7 C8 1.512(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? 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 Cu1 O5 176.67(12) 8_566 . ? O4 Cu1 O9 90.22(16) 8_566 . ? O5 Cu1 O9 89.23(16) . . ? O4 Cu1 O7 88.84(14) 8_566 . ? O5 Cu1 O7 91.47(14) . . ? O9 Cu1 O7 175.6(2) . . ? O4 Cu1 O8 83.30(13) 8_566 . ? O5 Cu1 O8 99.98(14) . . ? O9 Cu1 O8 90.0(2) . . ? O7 Cu1 O8 94.14(18) . . ? C1 O2 H2 112(3) . . ? C3 O4 Cu1 127.0(3) . 8_465 ? C8 O5 Cu1 111.2(3) . . ? C5 N1 C2 118.1(3) . . ? C5 N1 C4 120.1(3) . . ? C2 N1 C4 121.5(3) . . ? C5 N2 C5 113.0(4) 2_656 . ? C5 N3 C6 113.2(3) . . ? C6 N4 C7 119.1(2) . 2_656 ? C6 N4 C7 119.1(2) . . ? C7 N4 C7 121.7(4) 2_656 . ? O1 C1 O2 119.8(4) . . ? O1 C1 C2 121.3(4) . . ? O2 C1 C2 118.8(4) . . ? N1 C2 C1 114.6(3) . . ? N1 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N1 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? O3 C3 O4 125.7(4) . . ? O3 C3 C4 120.5(3) . . ? O4 C3 C4 113.8(3) . . ? N1 C4 C3 114.2(3) . . ? N1 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? N3 C5 N2 127.2(4) . . ? N3 C5 N1 117.7(3) . . ? N2 C5 N1 115.1(3) . . ? N3 C6 N3 126.3(5) 2_656 . ? N3 C6 N4 116.9(2) 2_656 . ? N3 C6 N4 116.9(2) . . ? N4 C7 C8 114.0(3) . . ? N4 C7 H7A 108.7 . . ? C8 C7 H7A 108.8 . . ? N4 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.6 . . ? O6 C8 O5 122.9(4) . . ? O6 C8 C7 118.6(4) . . ? O5 C8 C7 118.4(4) . . ? 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 O9 Cu1 O5 C8 76.2(3) . . . . ? O7 Cu1 O5 C8 -99.5(3) . . . . ? O8 Cu1 O5 C8 166.0(3) . . . . ? C5 N1 C2 C1 -67.8(4) . . . . ? C4 N1 C2 C1 106.8(4) . . . . ? O1 C1 C2 N1 160.3(4) . . . . ? O2 C1 C2 N1 -21.7(5) . . . . ? Cu1 O4 C3 O3 11.6(6) 8_465 . . . ? Cu1 O4 C3 C4 -167.7(3) 8_465 . . . ? C5 N1 C4 C3 77.3(4) . . . . ? C2 N1 C4 C3 -97.1(4) . . . . ? O3 C3 C4 N1 2.2(6) . . . . ? O4 C3 C4 N1 -178.4(3) . . . . ? C6 N3 C5 N2 -2.0(5) . . . . ? C6 N3 C5 N1 179.0(3) . . . . ? C5 N2 C5 N3 1.1(3) 2_656 . . . ? C5 N2 C5 N1 -179.9(4) 2_656 . . . ? C2 N1 C5 N3 178.4(3) . . . . ? C4 N1 C5 N3 3.8(5) . . . . ? C2 N1 C5 N2 -0.7(4) . . . . ? C4 N1 C5 N2 -175.3(3) . . . . ? C5 N3 C6 N3 0.9(2) . . . 2_656 ? C5 N3 C6 N4 -179.1(2) . . . . ? C7 N4 C6 N3 177.2(3) 2_656 . . 2_656 ? C7 N4 C6 N3 -2.8(3) . . . 2_656 ? C7 N4 C6 N3 -2.8(3) 2_656 . . . ? C7 N4 C6 N3 177.2(3) . . . . ? C6 N4 C7 C8 -73.6(4) . . . . ? C7 N4 C7 C8 106.4(4) 2_656 . . . ? Cu1 O5 C8 O6 10.7(5) . . . . ? Cu1 O5 C8 C7 -165.6(3) . . . . ? N4 C7 C8 O6 166.1(4) . . . . ? N4 C7 C8 O5 -17.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.551 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 943177' ####################################################################### # # 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_Solid3b _audit_creation_method 'SHELXTL-NT2000 ver.6.12' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 Cu2 N6 O16, 4(O)' _chemical_formula_sum 'C15 H13 Cu2 N6 O20' _chemical_formula_weight 724.41 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' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.045(4) _cell_length_b 12.656(3) _cell_length_c 21.157(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.688(4) _cell_angle_gamma 90.00 _cell_volume 5366.9(19) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6560 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 25.30 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.434 _exptl_crystal_size_mid 0.285 _exptl_crystal_size_min 0.191 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3366 _exptl_absorpt_coefficient_mu 1.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.567 _exptl_absorpt_correction_T_max 0.724 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23407 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4722 _reflns_number_gt 4268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+246.2123P] 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 0? _refine_ls_number_reflns 4722 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1161 _refine_ls_R_factor_gt 0.1139 _refine_ls_wR_factor_ref 0.2279 _refine_ls_wR_factor_gt 0.2269 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 Cu1 Cu 0.23489(6) -0.17836(11) 0.39699(6) 0.0311(4) Uani 1 1 d . . . Cu2 Cu 0.53296(7) 0.60669(12) 0.46400(8) 0.0435(5) Uani 1 1 d . . . O1 O 0.4588(4) 0.1049(8) 0.7085(4) 0.053(2) Uani 1 1 d . . . O2 O 0.3824(4) 0.1587(10) 0.7737(4) 0.070(3) Uani 1 1 d . . . O3 O 0.2795(4) -0.0973(8) 0.5817(5) 0.054(2) Uani 1 1 d . . . O4 O 0.3768(4) -0.2106(6) 0.4600(4) 0.042(2) Uani 1 1 d . . . O5 O 0.3157(3) -0.0924(6) 0.4066(4) 0.0358(18) Uani 1 1 d . . . O6 O 0.2059(3) -0.1534(5) 0.4846(3) 0.0282(16) Uani 1 1 d . . . O7 O 0.1574(4) -0.2707(6) 0.3846(4) 0.0372(18) Uani 1 1 d . . . O8 O 0.2622(4) -0.2130(8) 0.3109(4) 0.049(2) Uani 1 1 d . . . O9 O 0.1795(4) -0.0318(6) 0.3658(4) 0.0377(18) Uani 1 1 d . . . O10 O 0.3057(4) 0.0706(8) 0.3244(5) 0.056(3) Uani 1 1 d . . . H10 H 0.3165 0.0213 0.3476 0.084 Uiso 1 1 calc R . . O11 O 0.3566(6) 0.1963(10) 0.2723(5) 0.085(4) Uani 1 1 d . . . O12 O 0.4457(4) 0.4801(7) 0.4608(5) 0.051(2) Uani 1 1 d . . . O13 O 0.3871(5) 0.5434(9) 0.3818(5) 0.065(3) Uani 1 1 d . . . O14 O 0.5884(4) 0.5229(7) 0.4104(4) 0.049(2) Uani 1 1 d . . . O15 O 0.4947(4) 0.6757(8) 0.3877(5) 0.055(2) Uani 1 1 d . . . O16 O 0.4868(4) 0.7130(8) 0.5143(5) 0.057(3) Uani 1 1 d . . . O1W O 0.4656(7) 0.6606(12) 0.6364(7) 0.108(5) Uani 1 1 d . . . O2W O 0.5614(10) 0.6353(14) 0.2755(7) 0.143(7) Uani 1 1 d . . . O3W O 0.3597(8) 0.3494(12) 0.2166(7) 0.044(5) Uani 0.50 1 d P . . O4W O 0.2965(12) 0.558(3) 0.2794(9) 0.269(18) Uani 1 1 d . . . O5W O 0.429(3) 0.410(3) 0.2624(16) 0.170(18) Uani 0.50 1 d P . . N1 N 0.3709(4) 0.0518(8) 0.6174(4) 0.033(2) Uani 1 1 d . . . N2 N 0.3945(4) 0.0477(7) 0.5117(4) 0.030(2) Uani 1 1 d . . . N3 N 0.4175(4) 0.0486(7) 0.4060(4) 0.029(2) Uani 1 1 d . . . N4 N 0.3741(4) 0.2032(7) 0.4500(4) 0.0280(19) Uani 1 1 d . . . N5 N 0.3372(5) 0.3539(7) 0.4993(4) 0.035(2) Uani 1 1 d . . . N6 N 0.3524(4) 0.2026(7) 0.5608(4) 0.030(2) Uani 1 1 d . . . C1 C 0.3989(5) 0.1242(9) 0.7230(5) 0.033(3) Uani 1 1 d . . . C2 C 0.3452(5) 0.1030(10) 0.6743(5) 0.034(3) Uani 1 1 d . . . H2A H 0.3114 0.0581 0.6927 0.041 Uiso 1 1 calc R . . H2B H 0.3242 0.1692 0.6625 0.041 Uiso 1 1 calc R . . C3 C 0.3310(5) -0.1332(11) 0.6043(5) 0.039(3) Uani 1 1 d . . . C4 C 0.3874(6) -0.0592(10) 0.6216(5) 0.037(3) Uani 1 1 d . . . H4A H 0.4019 -0.0746 0.6645 0.045 Uiso 1 1 calc R . . H4B H 0.4246 -0.0733 0.5940 0.045 Uiso 1 1 calc R . . C5 C 0.3716(5) 0.1021(9) 0.5615(5) 0.031(2) Uani 1 1 d . . . C6 C 0.3945(5) 0.1016(9) 0.4576(5) 0.031(2) Uani 1 1 d . . . C7 C 0.4327(5) -0.0634(8) 0.4144(5) 0.026(2) Uani 1 1 d . . . H7A H 0.4650 -0.0710 0.4486 0.031 Uiso 1 1 calc R . . H7B H 0.4530 -0.0900 0.3762 0.031 Uiso 1 1 calc R . . C8 C 0.3710(5) -0.1313(9) 0.4293(5) 0.028(2) Uani 1 1 d . . . C9 C 0.4222(6) 0.1019(11) 0.3480(5) 0.048(3) Uani 1 1 d . . . H9A H 0.4502 0.0600 0.3207 0.057 Uiso 1 1 calc R . . H9B H 0.4453 0.1680 0.3558 0.057 Uiso 1 1 calc R . . C10 C 0.3582(7) 0.1270(11) 0.3116(6) 0.050(3) Uani 1 1 d . . . C11 C 0.1522(5) 0.0225(9) 0.4058(5) 0.033(3) Uani 1 1 d . . . C12 C 0.3544(5) 0.2502(8) 0.5024(6) 0.032(2) Uani 1 1 d . . . C13 C 0.3058(6) 0.4049(9) 0.5533(6) 0.040(3) Uani 1 1 d . . . H13A H 0.2882 0.3498 0.5803 0.048 Uiso 1 1 calc R . . H13B H 0.2680 0.4454 0.5375 0.048 Uiso 1 1 calc R . . C14 C 0.3359(6) 0.4063(9) 0.4387(6) 0.043(3) Uani 1 1 d . . . H14A H 0.2948 0.4464 0.4352 0.051 Uiso 1 1 calc R . . H14B H 0.3350 0.3529 0.4059 0.051 Uiso 1 1 calc R . . C15 C 0.3936(6) 0.4799(9) 0.4266(6) 0.039(3) 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 Cu1 0.0257(7) 0.0335(7) 0.0341(7) 0.0117(6) 0.0033(5) 0.0028(6) Cu2 0.0286(7) 0.0383(9) 0.0639(11) -0.0020(8) 0.0065(7) 0.0042(6) O1 0.039(5) 0.084(7) 0.037(5) -0.021(5) 0.005(4) 0.000(5) O2 0.040(5) 0.121(10) 0.048(6) -0.041(6) 0.005(4) -0.003(6) O3 0.032(4) 0.056(6) 0.073(6) 0.010(5) -0.014(4) 0.004(4) O4 0.028(4) 0.039(5) 0.058(5) 0.022(4) 0.001(4) 0.006(3) O5 0.024(4) 0.044(5) 0.039(4) 0.003(4) -0.004(3) -0.006(3) O6 0.034(4) 0.024(4) 0.026(4) 0.014(3) -0.003(3) -0.001(3) O7 0.036(4) 0.034(5) 0.041(5) 0.004(4) -0.007(3) 0.001(4) O8 0.043(5) 0.069(6) 0.035(4) -0.010(4) 0.014(4) -0.011(4) O9 0.040(4) 0.030(4) 0.042(5) -0.004(4) 0.000(4) 0.003(4) O10 0.049(5) 0.059(7) 0.061(6) 0.025(5) -0.004(4) -0.005(5) O11 0.103(9) 0.081(9) 0.070(7) 0.045(7) -0.012(6) -0.019(7) O12 0.031(4) 0.056(6) 0.068(6) 0.008(5) 0.005(4) 0.002(4) O13 0.052(6) 0.068(7) 0.074(7) 0.026(6) -0.007(5) -0.017(5) O14 0.030(4) 0.044(5) 0.072(6) -0.012(5) 0.005(4) 0.006(4) O15 0.044(5) 0.053(6) 0.069(6) 0.020(5) 0.007(4) 0.002(4) O16 0.037(5) 0.054(6) 0.080(7) -0.016(5) -0.014(5) 0.019(4) O1W 0.083(9) 0.119(12) 0.122(12) -0.039(10) 0.008(8) -0.001(8) O2W 0.206(18) 0.137(15) 0.087(11) -0.007(10) 0.059(11) -0.023(13) O3W 0.054(10) 0.030(9) 0.046(9) 0.034(7) -0.048(8) -0.009(7) O4W 0.20(2) 0.52(5) 0.090(13) 0.04(2) -0.043(14) -0.17(3) O5W 0.33(6) 0.09(2) 0.09(2) 0.01(2) 0.02(3) 0.03(3) N1 0.039(5) 0.039(5) 0.022(4) 0.001(4) -0.002(4) 0.004(4) N2 0.032(5) 0.035(5) 0.023(4) -0.008(4) -0.002(4) 0.009(4) N3 0.034(5) 0.031(5) 0.024(4) -0.006(4) 0.009(4) -0.004(4) N4 0.033(5) 0.027(5) 0.024(4) 0.002(4) 0.005(4) -0.003(4) N5 0.051(6) 0.015(4) 0.038(5) 0.002(4) 0.001(4) -0.011(4) N6 0.032(5) 0.027(5) 0.030(5) -0.005(4) 0.005(4) 0.004(4) C1 0.039(6) 0.038(7) 0.022(5) -0.006(5) 0.012(5) 0.008(5) C2 0.036(6) 0.039(6) 0.027(6) 0.000(5) 0.009(5) 0.010(5) C3 0.029(6) 0.066(9) 0.023(6) 0.010(6) 0.001(4) 0.007(6) C4 0.039(6) 0.049(7) 0.024(5) 0.010(5) -0.006(5) 0.011(5) C5 0.013(4) 0.040(6) 0.038(6) -0.014(5) -0.013(4) 0.005(4) C6 0.021(5) 0.040(6) 0.030(6) -0.010(5) -0.003(4) -0.003(5) C7 0.017(5) 0.038(6) 0.023(5) -0.010(4) -0.001(4) -0.002(4) C8 0.025(5) 0.036(6) 0.025(5) -0.005(5) -0.003(4) -0.001(5) C9 0.057(8) 0.062(8) 0.024(6) -0.009(6) 0.029(6) -0.003(7) C10 0.048(7) 0.052(9) 0.050(8) 0.015(7) 0.001(6) 0.000(6) C11 0.031(6) 0.027(6) 0.043(7) 0.008(5) 0.010(5) 0.015(5) C12 0.023(5) 0.020(5) 0.052(7) 0.010(5) 0.003(5) -0.001(4) C13 0.043(7) 0.025(6) 0.051(7) 0.000(5) 0.007(6) -0.004(5) C14 0.054(7) 0.017(6) 0.057(8) -0.005(5) 0.004(6) -0.012(5) C15 0.048(7) 0.022(6) 0.046(7) -0.005(5) 0.008(6) -0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O8 1.958(8) . ? Cu1 O7 1.958(8) . ? Cu1 O5 1.961(7) . ? Cu1 O6 1.976(7) . ? Cu1 O9 2.256(8) . ? Cu2 O14 1.917(8) . ? Cu2 O16 1.955(9) . ? Cu2 O12 1.976(9) 5_666 ? Cu2 O15 1.983(9) . ? Cu2 O12 2.373(9) . ? O1 C1 1.266(13) . ? O2 C1 1.208(13) . ? O3 C3 1.220(13) . ? O4 C8 1.201(13) . ? O5 C8 1.299(12) . ? O7 C3 1.259(15) 7_546 ? O9 C11 1.224(13) . ? O10 C10 1.303(15) . ? O10 H10 0.8200 . ? O11 C10 1.208(16) . ? O12 C15 1.264(15) . ? O12 Cu2 1.976(9) 5_666 ? O13 C15 1.248(15) . ? O14 C11 1.282(13) 3 ? N1 C5 1.345(14) . ? N1 C4 1.445(15) . ? N1 C2 1.465(13) . ? N2 C6 1.334(14) . ? N2 C5 1.343(13) . ? N3 C6 1.366(13) . ? N3 C9 1.403(15) . ? N3 C7 1.461(14) . ? N4 C12 1.324(14) . ? N4 C6 1.358(14) . ? N5 C12 1.359(13) . ? N5 C14 1.442(15) . ? N5 C13 1.462(14) . ? N6 C5 1.329(14) . ? N6 C12 1.374(14) . ? C1 C2 1.505(16) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O7 1.259(15) 7_546 ? C3 C4 1.509(17) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C7 C8 1.540(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.523(18) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 O14 1.282(13) 3_445 ? C11 C13 1.511(16) 7_556 ? C13 C11 1.511(17) 7_556 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.509(15) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 O8 Cu1 O7 88.4(3) . . ? O8 Cu1 O5 88.9(3) . . ? O7 Cu1 O5 176.5(3) . . ? O8 Cu1 O6 176.2(4) . . ? O7 Cu1 O6 88.8(3) . . ? O5 Cu1 O6 93.8(3) . . ? O8 Cu1 O9 93.1(4) . . ? O7 Cu1 O9 93.7(3) . . ? O5 Cu1 O9 88.7(3) . . ? O6 Cu1 O9 89.6(3) . . ? O14 Cu2 O16 169.7(4) . . ? O14 Cu2 O12 92.7(4) . 5_666 ? O16 Cu2 O12 92.5(4) . 5_666 ? O14 Cu2 O15 89.0(4) . . ? O16 Cu2 O15 87.7(4) . . ? O12 Cu2 O15 168.2(4) 5_666 . ? O14 Cu2 O12 92.4(3) . . ? O16 Cu2 O12 97.3(4) . . ? O12 Cu2 O12 78.5(4) 5_666 . ? O15 Cu2 O12 89.8(4) . . ? C8 O5 Cu1 121.9(7) . . ? C3 O7 Cu1 114.0(7) 7_546 . ? C11 O9 Cu1 118.9(7) . . ? C10 O10 H10 109.5 . . ? C15 O12 Cu2 129.1(8) . 5_666 ? C15 O12 Cu2 128.4(8) . . ? Cu2 O12 Cu2 101.5(4) 5_666 . ? C11 O14 Cu2 129.2(8) 3 . ? C5 N1 C4 120.6(9) . . ? C5 N1 C2 121.4(9) . . ? C4 N1 C2 117.5(9) . . ? C6 N2 C5 114.4(10) . . ? C6 N3 C9 119.3(10) . . ? C6 N3 C7 116.8(9) . . ? C9 N3 C7 123.9(9) . . ? C12 N4 C6 114.7(9) . . ? C12 N5 C14 119.3(10) . . ? C12 N5 C13 120.0(9) . . ? C14 N5 C13 119.2(9) . . ? C5 N6 C12 114.7(9) . . ? O2 C1 O1 123.8(11) . . ? O2 C1 C2 118.1(10) . . ? O1 C1 C2 118.1(9) . . ? N1 C2 C1 112.7(8) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? O3 C3 O7 125.8(12) . 7_546 ? O3 C3 C4 119.4(12) . . ? O7 C3 C4 114.8(10) 7_546 . ? N1 C4 C3 114.8(9) . . ? N1 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? N1 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.5 . . ? N6 C5 N2 125.7(11) . . ? N6 C5 N1 117.2(9) . . ? N2 C5 N1 117.0(10) . . ? N2 C6 N4 125.6(9) . . ? N2 C6 N3 116.0(10) . . ? N4 C6 N3 118.3(10) . . ? N3 C7 C8 113.6(8) . . ? N3 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N3 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? O4 C8 O5 126.4(10) . . ? O4 C8 C7 120.2(9) . . ? O5 C8 C7 113.4(9) . . ? N3 C9 C10 118.6(10) . . ? N3 C9 H9A 107.7 . . ? C10 C9 H9A 107.7 . . ? N3 C9 H9B 107.7 . . ? C10 C9 H9B 107.7 . . ? H9A C9 H9B 107.1 . . ? O11 C10 O10 121.8(13) . . ? O11 C10 C9 121.0(13) . . ? O10 C10 C9 117.2(11) . . ? O9 C11 O14 120.6(11) . 3_445 ? O9 C11 C13 119.0(10) . 7_556 ? O14 C11 C13 120.2(10) 3_445 7_556 ? N4 C12 N5 118.1(10) . . ? N4 C12 N6 124.7(9) . . ? N5 C12 N6 117.2(10) . . ? N5 C13 C11 118.3(9) . 7_556 ? N5 C13 H13A 107.7 . . ? C11 C13 H13A 107.7 7_556 . ? N5 C13 H13B 107.7 . . ? C11 C13 H13B 107.7 7_556 . ? H13A C13 H13B 107.1 . . ? N5 C14 C15 115.5(11) . . ? N5 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? N5 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.5 . . ? O13 C15 O12 120.8(11) . . ? O13 C15 C14 117.0(12) . . ? O12 C15 C14 122.2(11) . . ? 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 O8 Cu1 O5 C8 -91.5(8) . . . . ? O6 Cu1 O5 C8 85.8(8) . . . . ? O9 Cu1 O5 C8 175.4(8) . . . . ? O8 Cu1 O7 C3 84.7(8) . . . 7_546 ? O9 Cu1 O7 C3 177.7(8) . . . 7_546 ? O8 Cu1 O9 C11 -179.1(8) . . . . ? O7 Cu1 O9 C11 92.3(8) . . . . ? O5 Cu1 O9 C11 -90.3(9) . . . . ? O6 Cu1 O9 C11 3.5(8) . . . . ? O14 Cu2 O12 C15 -98.4(10) . . . . ? O16 Cu2 O12 C15 78.2(10) . . . . ? O12 Cu2 O12 C15 169.3(12) 5_666 . . . ? O15 Cu2 O12 C15 -9.4(10) . . . . ? O14 Cu2 O12 Cu2 92.3(4) . . . 5_666 ? O16 Cu2 O12 Cu2 -91.1(4) . . . 5_666 ? O12 Cu2 O12 Cu2 0.0 5_666 . . 5_666 ? O15 Cu2 O12 Cu2 -178.7(4) . . . 5_666 ? O16 Cu2 O14 C11 44(3) . . . 3 ? O12 Cu2 O14 C11 -76.7(11) 5_666 . . 3 ? O15 Cu2 O14 C11 115.0(11) . . . 3 ? O12 Cu2 O14 C11 -155.3(10) . . . 3 ? C5 N1 C2 C1 -112.6(11) . . . . ? C4 N1 C2 C1 75.3(13) . . . . ? O2 C1 C2 N1 -174.4(12) . . . . ? O1 C1 C2 N1 5.7(16) . . . . ? C5 N1 C4 C3 -81.3(12) . . . . ? C2 N1 C4 C3 90.8(11) . . . . ? O3 C3 C4 N1 8.1(15) . . . . ? O7 C3 C4 N1 -171.6(9) 7_546 . . . ? C12 N6 C5 N2 2.9(15) . . . . ? C12 N6 C5 N1 179.7(9) . . . . ? C6 N2 C5 N6 -2.7(15) . . . . ? C6 N2 C5 N1 -179.5(9) . . . . ? C4 N1 C5 N6 176.4(9) . . . . ? C2 N1 C5 N6 4.6(14) . . . . ? C4 N1 C5 N2 -6.5(14) . . . . ? C2 N1 C5 N2 -178.3(9) . . . . ? C5 N2 C6 N4 0.1(15) . . . . ? C5 N2 C6 N3 180.0(9) . . . . ? C12 N4 C6 N2 1.8(15) . . . . ? C12 N4 C6 N3 -178.0(9) . . . . ? C9 N3 C6 N2 -176.9(10) . . . . ? C7 N3 C6 N2 6.3(13) . . . . ? C9 N3 C6 N4 3.0(14) . . . . ? C7 N3 C6 N4 -173.9(8) . . . . ? C6 N3 C7 C8 64.7(11) . . . . ? C9 N3 C7 C8 -112.0(11) . . . . ? Cu1 O5 C8 O4 -18.9(15) . . . . ? Cu1 O5 C8 C7 162.4(6) . . . . ? N3 C7 C8 O4 -151.3(10) . . . . ? N3 C7 C8 O5 27.5(12) . . . . ? C6 N3 C9 C10 -73.1(15) . . . . ? C7 N3 C9 C10 103.5(13) . . . . ? N3 C9 C10 O11 158.8(14) . . . . ? N3 C9 C10 O10 -21.5(18) . . . . ? Cu1 O9 C11 O14 -107.2(11) . . . 3_445 ? Cu1 O9 C11 C13 77.1(11) . . . 7_556 ? C6 N4 C12 N5 175.9(9) . . . . ? C6 N4 C12 N6 -1.6(15) . . . . ? C14 N5 C12 N4 4.7(15) . . . . ? C13 N5 C12 N4 170.8(9) . . . . ? C14 N5 C12 N6 -177.5(9) . . . . ? C13 N5 C12 N6 -11.5(15) . . . . ? C5 N6 C12 N4 -0.5(15) . . . . ? C5 N6 C12 N5 -178.1(9) . . . . ? C12 N5 C13 C11 103.8(12) . . . 7_556 ? C14 N5 C13 C11 -90.1(13) . . . 7_556 ? C12 N5 C14 C15 -104.7(12) . . . . ? C13 N5 C14 C15 89.2(13) . . . . ? Cu2 O12 C15 O13 177.2(9) 5_666 . . . ? Cu2 O12 C15 O13 10.8(17) . . . . ? Cu2 O12 C15 C14 -0.9(17) 5_666 . . . ? Cu2 O12 C15 C14 -167.4(8) . . . . ? N5 C14 C15 O13 -164.6(11) . . . . ? N5 C14 C15 O12 13.6(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.873 _refine_diff_density_min -1.216 _refine_diff_density_rms 0.167 _database_code_depnum_ccdc_archive 'CCDC 943178' ####################################################################### # # 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_solid4b _audit_creation_method 'SHELXTL-NT2000 ver.6.12' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N6 O19 Zn2, 2(O)' _chemical_formula_sum 'C15 H14 N6 O21 Zn2 ' _chemical_formula_weight 745.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_hall '-P 2yn' 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 14.005(6) _cell_length_b 10.324(4) _cell_length_c 19.368(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.130(7) _cell_angle_gamma 90.00 _cell_volume 2738(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5803 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.83 _exptl_crystal_description needle _exptl_crystal_colour white _exptl_crystal_size_max 0.535 _exptl_crystal_size_mid 0.384 _exptl_crystal_size_min 0.173 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 1.856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.429 _exptl_absorpt_correction_T_max 0.725 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23894 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4835 _reflns_number_gt 4258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+4.1815P] 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 4835 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.28536(3) 0.62527(5) 0.23408(3) 0.02085(17) Uani 1 1 d . . . Zn2 Zn 0.38586(4) 0.27604(5) 0.06645(3) 0.02377(18) Uani 1 1 d . . . O1 O 0.3531(2) 0.5102(3) 0.17853(16) 0.0270(7) Uani 1 1 d . . . O2 O 0.4288(2) 0.4615(3) 0.09184(16) 0.0275(7) Uani 1 1 d . . . O3 O 0.4514(2) 0.2014(3) 0.17769(16) 0.0270(7) Uani 1 1 d . . . O4 O 0.2640(2) 0.2798(3) 0.11334(17) 0.0307(8) Uani 1 1 d . . . O5 O 0.3605(2) 0.0865(3) 0.03574(18) 0.0355(8) Uani 1 1 d . . . O6 O 0.3089(3) 0.3405(4) -0.03092(19) 0.0467(10) Uani 1 1 d . . . O7 O 0.5221(2) 0.2529(3) 0.04146(17) 0.0299(7) Uani 1 1 d . . . O8 O 0.3746(2) 0.5766(3) 0.33323(16) 0.0272(7) Uani 1 1 d . . . O9 O 0.1748(2) 0.6706(3) 0.14494(16) 0.0308(8) Uani 1 1 d . . . O10 O 0.3211(2) 1.0268(3) 0.23049(15) 0.0230(7) Uani 1 1 d . . . O11 O 0.2915(2) 0.8190(3) 0.25061(16) 0.0250(7) Uani 1 1 d . . . O12 O 0.7792(2) 0.5365(3) 0.17910(17) 0.0341(8) Uani 1 1 d . . . H12 H 0.8015 0.5330 0.2217 0.051 Uiso 1 1 calc R . . O13 O 0.6732(2) 0.4294(3) 0.10065(17) 0.0357(8) Uani 1 1 d . . . O14 O 0.8737(2) 0.5650(3) 0.30562(16) 0.0276(7) Uani 1 1 d . . . O15 O 0.9064(2) 0.5132(4) 0.41901(18) 0.0376(9) Uani 1 1 d . . . O16 O 0.7219(3) 0.5642(4) 0.57449(18) 0.0414(9) Uani 1 1 d . . . O17 O 0.5724(2) 0.6107(4) 0.52137(19) 0.0397(9) Uani 1 1 d . . . H17 H 0.5438 0.6593 0.4903 0.060 Uiso 1 1 calc R . . O18 O 0.4486(2) 0.7524(3) 0.44314(18) 0.0337(8) Uani 1 1 d . . . O19 O 0.4123(3) 0.9551(4) 0.4137(2) 0.0476(10) Uani 1 1 d . . . O1W O 0.0340(3) 0.8289(4) 0.18687(19) 0.0396(9) Uani 1 1 d . . . O2W O 0.1242(3) 0.2470(5) 0.9279(2) 0.0644(13) Uani 1 1 d . . . N1 N 0.4599(3) 0.7430(3) 0.19978(18) 0.0199(8) Uani 1 1 d . . . N2 N 0.5761(2) 0.5871(3) 0.24144(18) 0.0187(7) Uani 1 1 d . . . N3 N 0.6954(2) 0.4397(3) 0.28820(18) 0.0202(8) Uani 1 1 d . . . N4 N 0.6682(2) 0.6061(4) 0.36011(18) 0.0219(8) Uani 1 1 d . . . N5 N 0.6369(3) 0.7800(4) 0.42713(18) 0.0224(8) Uani 1 1 d . . . N6 N 0.5493(3) 0.7670(3) 0.31322(18) 0.0200(8) Uani 1 1 d . . . C1 C 0.4067(3) 0.5385(4) 0.1355(2) 0.0199(9) Uani 1 1 d . . . C2 C 0.4456(3) 0.6753(4) 0.1323(2) 0.0239(10) Uani 1 1 d . . . H2A H 0.5074 0.6716 0.1173 0.029 Uiso 1 1 calc R . . H2B H 0.4001 0.7242 0.0972 0.029 Uiso 1 1 calc R . . C3 C 0.4311(3) 0.8782(4) 0.2003(2) 0.0206(9) Uani 1 1 d . . . H3A H 0.4202 0.9106 0.1522 0.025 Uiso 1 1 calc R . . H3B H 0.4852 0.9267 0.2279 0.025 Uiso 1 1 calc R . . C4 C 0.3399(3) 0.9067(4) 0.2295(2) 0.0172(9) Uani 1 1 d . . . C5 C 0.5321(3) 0.6974(4) 0.2539(2) 0.0179(9) Uani 1 1 d . . . C6 C 0.6442(3) 0.5476(4) 0.2971(2) 0.0190(9) Uani 1 1 d . . . C7 C 0.6763(3) 0.3754(4) 0.2198(2) 0.0241(10) Uani 1 1 d . . . H7A H 0.6067 0.3594 0.2054 0.029 Uiso 1 1 calc R . . H7B H 0.7090 0.2920 0.2249 0.029 Uiso 1 1 calc R . . C8 C 0.7094(3) 0.4508(5) 0.1619(2) 0.0264(10) Uani 1 1 d . . . C9 C 0.7757(3) 0.4010(4) 0.3448(2) 0.0228(10) Uani 1 1 d . . . H9A H 0.8013 0.3186 0.3328 0.027 Uiso 1 1 calc R . . H9B H 0.7515 0.3891 0.3878 0.027 Uiso 1 1 calc R . . C10 C 0.8578(3) 0.5005(4) 0.3581(2) 0.0253(10) Uani 1 1 d . . . C11 C 0.6175(3) 0.7148(4) 0.3645(2) 0.0194(9) Uani 1 1 d . . . C12 C 0.7053(3) 0.7285(5) 0.4860(2) 0.0280(10) Uani 1 1 d . . . H12A H 0.7317 0.7996 0.5168 0.034 Uiso 1 1 calc R . . H12B H 0.7589 0.6900 0.4687 0.034 Uiso 1 1 calc R . . C13 C 0.6648(3) 0.6273(5) 0.5295(2) 0.0278(11) Uani 1 1 d . . . C14 C 0.5801(3) 0.8966(5) 0.4335(2) 0.0269(10) Uani 1 1 d . . . H14A H 0.5864 0.9568 0.3963 0.032 Uiso 1 1 calc R . . H14B H 0.6065 0.9381 0.4784 0.032 Uiso 1 1 calc R . . C15 C 0.4726(3) 0.8670(5) 0.4289(2) 0.0286(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0239(3) 0.0164(3) 0.0239(3) -0.0004(2) 0.0087(2) -0.0014(2) Zn2 0.0246(3) 0.0217(3) 0.0256(3) -0.0041(2) 0.0066(2) -0.0024(2) O1 0.0296(17) 0.0236(17) 0.0315(17) -0.0073(14) 0.0145(14) -0.0028(13) O2 0.0332(17) 0.0226(17) 0.0292(17) -0.0069(14) 0.0122(14) -0.0026(14) O3 0.0277(16) 0.0236(18) 0.0293(17) 0.0019(14) 0.0053(14) 0.0024(13) O4 0.0260(17) 0.034(2) 0.0347(19) -0.0009(15) 0.0114(14) -0.0004(14) O5 0.043(2) 0.0252(18) 0.041(2) -0.0108(16) 0.0155(16) -0.0088(15) O6 0.055(2) 0.042(2) 0.035(2) 0.0090(17) -0.0108(18) -0.0128(19) O7 0.0283(17) 0.0320(19) 0.0319(18) -0.0048(14) 0.0117(14) -0.0002(14) O8 0.0282(17) 0.0293(18) 0.0233(16) 0.0013(14) 0.0041(13) 0.0014(14) O9 0.0355(18) 0.0292(19) 0.0251(17) 0.0069(14) 0.0007(14) -0.0039(15) O10 0.0240(15) 0.0170(16) 0.0295(17) -0.0023(13) 0.0088(13) 0.0039(13) O11 0.0266(16) 0.0197(17) 0.0299(17) -0.0017(13) 0.0089(14) -0.0029(13) O12 0.0337(19) 0.042(2) 0.0262(17) 0.0053(16) 0.0052(15) -0.0134(16) O13 0.0385(19) 0.039(2) 0.0281(19) -0.0042(16) 0.0036(15) -0.0094(16) O14 0.0255(16) 0.0297(19) 0.0279(17) 0.0052(14) 0.0060(13) -0.0065(14) O15 0.0357(19) 0.042(2) 0.0313(19) 0.0083(16) -0.0016(16) -0.0089(16) O16 0.047(2) 0.048(2) 0.0286(19) 0.0103(17) 0.0067(16) 0.0226(19) O17 0.0329(19) 0.042(2) 0.042(2) 0.0176(17) 0.0026(16) -0.0036(16) O18 0.0270(17) 0.039(2) 0.0372(19) 0.0034(16) 0.0106(15) -0.0023(15) O19 0.044(2) 0.048(3) 0.045(2) 0.0004(19) -0.0018(18) 0.0216(19) O1W 0.039(2) 0.038(2) 0.041(2) -0.0012(17) 0.0076(17) 0.0007(17) O2W 0.040(2) 0.102(4) 0.055(3) -0.020(3) 0.020(2) -0.019(2) N1 0.0242(19) 0.0159(19) 0.0173(18) -0.0038(14) -0.0010(15) 0.0063(15) N2 0.0203(18) 0.0164(18) 0.0187(18) -0.0018(15) 0.0022(14) 0.0023(15) N3 0.0200(18) 0.0152(19) 0.0261(19) -0.0010(15) 0.0062(15) 0.0019(15) N4 0.0185(18) 0.027(2) 0.0196(18) -0.0004(16) 0.0028(15) 0.0039(15) N5 0.0221(18) 0.027(2) 0.0178(19) -0.0016(16) 0.0035(15) 0.0025(15) N6 0.0240(19) 0.0168(19) 0.0179(18) -0.0023(15) 0.0015(15) 0.0011(15) C1 0.018(2) 0.021(2) 0.020(2) 0.0002(18) 0.0029(17) 0.0041(18) C2 0.027(2) 0.021(2) 0.021(2) -0.0033(18) -0.0007(18) 0.0037(19) C3 0.024(2) 0.014(2) 0.024(2) -0.0020(17) 0.0050(18) 0.0031(17) C4 0.019(2) 0.017(2) 0.014(2) -0.0043(17) -0.0002(16) 0.0013(17) C5 0.0151(19) 0.018(2) 0.022(2) 0.0001(17) 0.0055(17) 0.0013(17) C6 0.017(2) 0.017(2) 0.024(2) 0.0001(18) 0.0076(17) -0.0013(17) C7 0.024(2) 0.018(2) 0.031(2) -0.0030(19) 0.0075(19) 0.0012(18) C8 0.025(2) 0.025(3) 0.030(3) 0.000(2) 0.007(2) 0.000(2) C9 0.021(2) 0.019(2) 0.028(2) 0.0073(19) 0.0037(18) 0.0025(18) C10 0.018(2) 0.024(3) 0.034(3) 0.004(2) 0.006(2) 0.0040(18) C11 0.020(2) 0.020(2) 0.020(2) 0.0011(18) 0.0084(18) -0.0012(17) C12 0.024(2) 0.036(3) 0.022(2) -0.004(2) 0.0003(19) -0.003(2) C13 0.034(3) 0.029(3) 0.020(2) -0.006(2) 0.006(2) 0.006(2) C14 0.031(2) 0.027(3) 0.023(2) -0.0057(19) 0.0065(19) 0.001(2) C15 0.028(2) 0.039(3) 0.018(2) -0.004(2) 0.0030(19) 0.010(2) _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 1.974(3) . ? Zn1 O11 2.025(3) . ? Zn1 O10 2.039(3) 2_545 ? Zn1 O9 2.115(3) . ? Zn1 O8 2.120(3) . ? Zn2 O2 2.036(3) . ? Zn2 O5 2.054(3) . ? Zn2 O6 2.075(4) . ? Zn2 O7 2.078(3) . ? Zn2 O4 2.095(3) . ? Zn2 O3 2.291(3) . ? O1 C1 1.268(5) . ? O2 C1 1.245(5) . ? O10 C4 1.269(5) . ? O10 Zn1 2.039(3) 2 ? O11 C4 1.250(5) . ? O12 C8 1.309(6) . ? O12 H12 0.8200 . ? O13 C8 1.208(6) . ? O14 C10 1.273(5) . ? O15 C10 1.239(6) . ? O16 C13 1.238(6) . ? O17 C13 1.282(6) . ? O17 H17 0.8200 . ? O18 C15 1.276(6) . ? O19 C15 1.234(6) . ? N1 C5 1.377(5) . ? N1 C3 1.454(5) . ? N1 C2 1.458(5) . ? N2 C5 1.341(5) . ? N2 C6 1.344(5) . ? N3 C6 1.356(5) . ? N3 C9 1.451(5) . ? N3 C7 1.456(6) . ? N4 C6 1.339(5) . ? N4 C11 1.340(5) . ? N5 C11 1.363(5) . ? N5 C12 1.428(6) . ? N5 C14 1.462(6) . ? N6 C5 1.334(5) . ? N6 C11 1.339(5) . ? C1 C2 1.519(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.530(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C7 C8 1.516(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.523(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C12 C13 1.524(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.521(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 O11 132.17(12) . . ? O1 Zn1 O10 110.65(13) . 2_545 ? O11 Zn1 O10 116.67(12) . 2_545 ? O1 Zn1 O9 92.37(13) . . ? O11 Zn1 O9 84.83(13) . . ? O10 Zn1 O9 85.60(12) 2_545 . ? O1 Zn1 O8 95.27(13) . . ? O11 Zn1 O8 95.36(13) . . ? O10 Zn1 O8 84.88(12) 2_545 . ? O9 Zn1 O8 169.43(12) . . ? O2 Zn2 O5 171.95(12) . . ? O2 Zn2 O6 89.35(14) . . ? O5 Zn2 O6 90.97(15) . . ? O2 Zn2 O7 85.75(12) . . ? O5 Zn2 O7 86.25(13) . . ? O6 Zn2 O7 98.74(15) . . ? O2 Zn2 O4 95.94(12) . . ? O5 Zn2 O4 92.06(13) . . ? O6 Zn2 O4 94.22(15) . . ? O7 Zn2 O4 166.96(13) . . ? O2 Zn2 O3 92.84(12) . . ? O5 Zn2 O3 87.86(13) . . ? O6 Zn2 O3 172.54(14) . . ? O7 Zn2 O3 88.54(12) . . ? O4 Zn2 O3 78.47(12) . . ? C1 O1 Zn1 129.7(3) . . ? C1 O2 Zn2 131.4(3) . . ? C4 O10 Zn1 131.4(3) . 2 ? C4 O11 Zn1 132.2(3) . . ? C8 O12 H12 109.5 . . ? C13 O17 H17 109.5 . . ? C5 N1 C3 118.9(3) . . ? C5 N1 C2 117.3(3) . . ? C3 N1 C2 118.7(3) . . ? C5 N2 C6 112.9(3) . . ? C6 N3 C9 118.5(4) . . ? C6 N3 C7 119.3(4) . . ? C9 N3 C7 121.8(3) . . ? C6 N4 C11 113.6(4) . . ? C11 N5 C12 120.0(4) . . ? C11 N5 C14 118.2(4) . . ? C12 N5 C14 121.6(4) . . ? C5 N6 C11 113.2(4) . . ? O2 C1 O1 124.4(4) . . ? O2 C1 C2 115.1(4) . . ? O1 C1 C2 120.4(4) . . ? N1 C2 C1 113.1(4) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N1 C3 C4 116.2(3) . . ? N1 C3 H3A 108.2 . . ? C4 C3 H3A 108.2 . . ? N1 C3 H3B 108.2 . . ? C4 C3 H3B 108.2 . . ? H3A C3 H3B 107.4 . . ? O11 C4 O10 125.0(4) . . ? O11 C4 C3 122.3(4) . . ? O10 C4 C3 112.7(4) . . ? N6 C5 N2 127.3(4) . . ? N6 C5 N1 116.2(4) . . ? N2 C5 N1 116.5(4) . . ? N4 C6 N2 126.5(4) . . ? N4 C6 N3 116.6(4) . . ? N2 C6 N3 116.9(4) . . ? N3 C7 C8 114.4(4) . . ? N3 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N3 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? O13 C8 O12 120.7(4) . . ? O13 C8 C7 120.1(4) . . ? O12 C8 C7 119.1(4) . . ? N3 C9 C10 112.3(4) . . ? N3 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N3 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? O15 C10 O14 123.5(4) . . ? O15 C10 C9 118.4(4) . . ? O14 C10 C9 118.1(4) . . ? N6 C11 N4 126.5(4) . . ? N6 C11 N5 116.1(4) . . ? N4 C11 N5 117.5(4) . . ? N5 C12 C13 115.6(4) . . ? N5 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? N5 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? O16 C13 O17 120.1(5) . . ? O16 C13 C12 119.3(4) . . ? O17 C13 C12 120.5(4) . . ? N5 C14 C15 112.3(4) . . ? N5 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N5 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? O19 C15 O18 122.5(5) . . ? O19 C15 C14 119.1(5) . . ? O18 C15 C14 118.4(4) . . ? 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 O11 Zn1 O1 C1 -8.8(4) . . . . ? O10 Zn1 O1 C1 162.6(3) 2_545 . . . ? O9 Zn1 O1 C1 76.4(4) . . . . ? O8 Zn1 O1 C1 -110.9(4) . . . . ? O6 Zn2 O2 C1 110.7(4) . . . . ? O7 Zn2 O2 C1 -150.5(4) . . . . ? O4 Zn2 O2 C1 16.5(4) . . . . ? O3 Zn2 O2 C1 -62.2(4) . . . . ? O1 Zn1 O11 C4 -0.5(4) . . . . ? O10 Zn1 O11 C4 -171.5(3) 2_545 . . . ? O9 Zn1 O11 C4 -89.0(4) . . . . ? O8 Zn1 O11 C4 101.6(4) . . . . ? Zn2 O2 C1 O1 4.5(6) . . . . ? Zn2 O2 C1 C2 -172.9(3) . . . . ? Zn1 O1 C1 O2 -163.6(3) . . . . ? Zn1 O1 C1 C2 13.7(6) . . . . ? C5 N1 C2 C1 67.2(5) . . . . ? C3 N1 C2 C1 -138.3(4) . . . . ? O2 C1 C2 N1 -152.8(4) . . . . ? O1 C1 C2 N1 29.7(5) . . . . ? C5 N1 C3 C4 -97.9(4) . . . . ? C2 N1 C3 C4 108.0(4) . . . . ? Zn1 O11 C4 O10 163.1(3) . . . . ? Zn1 O11 C4 C3 -18.0(6) . . . . ? Zn1 O10 C4 O11 1.5(6) 2 . . . ? Zn1 O10 C4 C3 -177.5(3) 2 . . . ? N1 C3 C4 O11 -1.3(6) . . . . ? N1 C3 C4 O10 177.8(3) . . . . ? C11 N6 C5 N2 -1.3(6) . . . . ? C11 N6 C5 N1 177.5(3) . . . . ? C6 N2 C5 N6 0.1(6) . . . . ? C6 N2 C5 N1 -178.8(3) . . . . ? C3 N1 C5 N6 20.2(5) . . . . ? C2 N1 C5 N6 174.7(4) . . . . ? C3 N1 C5 N2 -160.8(4) . . . . ? C2 N1 C5 N2 -6.3(5) . . . . ? C11 N4 C6 N2 -0.7(6) . . . . ? C11 N4 C6 N3 177.6(4) . . . . ? C5 N2 C6 N4 1.0(6) . . . . ? C5 N2 C6 N3 -177.2(3) . . . . ? C9 N3 C6 N4 -4.2(5) . . . . ? C7 N3 C6 N4 -176.9(4) . . . . ? C9 N3 C6 N2 174.3(3) . . . . ? C7 N3 C6 N2 1.6(5) . . . . ? C6 N3 C7 C8 69.5(5) . . . . ? C9 N3 C7 C8 -103.0(5) . . . . ? N3 C7 C8 O13 -157.7(4) . . . . ? N3 C7 C8 O12 24.2(6) . . . . ? C6 N3 C9 C10 -64.0(5) . . . . ? C7 N3 C9 C10 108.5(4) . . . . ? N3 C9 C10 O15 148.4(4) . . . . ? N3 C9 C10 O14 -32.7(5) . . . . ? C5 N6 C11 N4 1.7(6) . . . . ? C5 N6 C11 N5 -178.6(3) . . . . ? C6 N4 C11 N6 -0.8(6) . . . . ? C6 N4 C11 N5 179.5(4) . . . . ? C12 N5 C11 N6 177.1(4) . . . . ? C14 N5 C11 N6 2.1(5) . . . . ? C12 N5 C11 N4 -3.2(6) . . . . ? C14 N5 C11 N4 -178.2(4) . . . . ? C11 N5 C12 C13 -83.4(5) . . . . ? C14 N5 C12 C13 91.4(5) . . . . ? N5 C12 C13 O16 169.2(4) . . . . ? N5 C12 C13 O17 -13.2(6) . . . . ? C11 N5 C14 C15 65.3(5) . . . . ? C12 N5 C14 C15 -109.6(4) . . . . ? N5 C14 C15 O19 -159.9(4) . . . . ? N5 C14 C15 O18 22.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.756 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 943179'