# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'En-Qing Gao' _publ_contact_author_email EQGAO@CHEM.ECNU.EDU.CN _publ_section_title ; Coordination compounds of bis(5-tetrazolyl)amine with manganese(II), zinc(II) and Cadmium(II): synthesis, structure and magnetic properties ; loop_ _publ_author_name 'En-Qing Gao.' 'Ai-Ling Cheng.' 'Na Liu.' 'Yan-Qing Wang.' 'Qi Yue.' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 634264' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H32 Mn7 N54 O14' _chemical_formula_weight 1541.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P-3c1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' _cell_length_a 14.289(3) _cell_length_b 14.289(3) _cell_length_c 13.738(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2429.1(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 766 _cell_measurement_theta_min 2.851 _cell_measurement_theta_max 21.577 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1538 _exptl_absorpt_coefficient_mu 1.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6027 _exptl_absorpt_correction_T_max 0.7051 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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_% 4.53 _diffrn_reflns_number 11645 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.12 _reflns_number_total 1805 _reflns_number_gt 1151 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0060P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1805 _refine_ls_number_parameters 149 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0441 _refine_ls_wR_factor_gt 0.0417 _refine_ls_goodness_of_fit_ref 0.807 _refine_ls_restrained_S_all 0.808 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.49789(3) 0.79755(3) 0.35026(3) 0.02293(12) Uani 1 1 d . . . Mn2 Mn 1.0000 1.0000 0.5000 0.0219(2) Uani 1 6 d S . . C1 C 0.6453(2) 0.6839(2) 0.37832(19) 0.0221(6) Uani 1 1 d . . . C2 C 0.7570(2) 0.8791(2) 0.38827(18) 0.0228(6) Uani 1 1 d . . . N1 N 0.55004(16) 0.67656(16) 0.36327(15) 0.0234(5) Uani 1 1 d . . . N2 N 0.47949(17) 0.56800(17) 0.36009(15) 0.0261(6) Uani 1 1 d . . . N3 N 0.53172(17) 0.51666(16) 0.37196(16) 0.0302(6) Uani 1 1 d . . . N4 N 0.63829(17) 0.58741(17) 0.38340(16) 0.0301(6) Uani 1 1 d . . . N5 N 0.74144(18) 0.77638(19) 0.38764(18) 0.0298(6) Uani 1 1 d D . . H5N H 0.7938(14) 0.7701(17) 0.3913(17) 0.013(7) Uiso 1 1 d D . . N9 N 0.85328(15) 0.96500(16) 0.40640(15) 0.0243(5) Uani 1 1 d . . . N8 N 0.83651(17) 1.04977(17) 0.39431(16) 0.0294(6) Uani 1 1 d . . . N7 N 0.73629(17) 1.01546(17) 0.37288(16) 0.0305(6) Uani 1 1 d . . . N6 N 0.68127(16) 0.90488(16) 0.36869(15) 0.0250(6) Uani 1 1 d . . . O1 O 0.3333 0.6667 0.3185(2) 0.0208(7) Uani 1 3 d SD . . H1 H 0.3333 0.6667 0.2611(14) 0.031 Uiso 1 3 d SD . . O2 O 0.51626(15) 0.82888(16) 0.19326(16) 0.0331(6) Uani 1 1 d . . . H2WB H 0.573(2) 0.855(2) 0.182(2) 0.050 Uiso 1 1 d . . . H2WA H 0.497(2) 0.872(2) 0.176(2) 0.050 Uiso 1 1 d . . . O3 O 0.45891(16) 0.77140(15) 0.50796(15) 0.0346(6) Uani 1 1 d . . . H3WB H 0.445(2) 0.712(2) 0.521(2) 0.052 Uiso 1 1 d . . . H3WA H 0.507(2) 0.823(2) 0.540(2) 0.052 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 Mn1 0.0161(2) 0.0187(2) 0.0347(3) 0.0004(2) -0.00044(19) 0.0092(2) Mn2 0.0151(3) 0.0151(3) 0.0355(7) 0.000 0.000 0.00755(16) C1 0.0169(15) 0.0194(15) 0.0281(17) -0.0039(13) -0.0037(12) 0.0077(13) C2 0.0193(15) 0.0193(15) 0.0285(17) 0.0005(13) -0.0007(12) 0.0088(13) N1 0.0150(12) 0.0184(13) 0.0353(15) -0.0040(11) -0.0042(10) 0.0073(11) N2 0.0192(13) 0.0200(13) 0.0375(15) -0.0011(11) -0.0022(10) 0.0086(11) N3 0.0238(14) 0.0214(13) 0.0461(17) -0.0049(11) -0.0063(12) 0.0120(12) N4 0.0225(13) 0.0203(13) 0.0485(16) -0.0062(12) -0.0096(12) 0.0116(12) N5 0.0113(13) 0.0219(14) 0.0588(18) -0.0049(12) -0.0070(12) 0.0103(12) N9 0.0157(12) 0.0151(12) 0.0393(15) 0.0022(11) -0.0021(10) 0.0057(10) N8 0.0201(13) 0.0206(13) 0.0441(16) 0.0039(11) -0.0043(11) 0.0075(11) N7 0.0224(14) 0.0203(13) 0.0466(17) 0.0045(11) -0.0060(11) 0.0090(12) N6 0.0171(13) 0.0165(12) 0.0395(16) 0.0024(11) -0.0031(10) 0.0071(11) O1 0.0187(10) 0.0187(10) 0.0250(19) 0.000 0.000 0.0093(5) O2 0.0264(12) 0.0341(13) 0.0412(14) 0.0057(10) 0.0032(11) 0.0170(11) O3 0.0368(13) 0.0239(12) 0.0384(14) -0.0033(11) -0.0035(10) 0.0115(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 2.192(2) . ? Mn1 O1 2.1952(8) . ? Mn1 N1 2.205(2) . ? Mn1 O3 2.222(2) . ? Mn1 N2 2.256(2) 2_665 ? Mn1 N6 2.294(2) . ? Mn2 N9 2.291(2) 7_776 ? Mn2 N9 2.291(2) 2_765 ? Mn2 N9 2.291(2) . ? Mn2 N9 2.291(2) 3_675 ? Mn2 N9 2.291(2) 9_656 ? Mn2 N9 2.291(2) 8_566 ? C1 N1 1.329(3) . ? C1 N4 1.333(3) . ? C1 N5 1.354(3) . ? C2 N9 1.331(3) . ? C2 N6 1.334(3) . ? C2 N5 1.370(3) . ? N1 N2 1.364(3) . ? N2 N3 1.292(3) . ? N2 Mn1 2.256(2) 3_565 ? N3 N4 1.351(3) . ? N5 H5N 0.799(15) . ? N9 N8 1.357(3) . ? N8 N7 1.295(3) . ? N7 N6 1.370(3) . ? O1 Mn1 2.1952(8) 2_665 ? O1 Mn1 2.1952(8) 3_565 ? O1 H1 0.789(18) . ? O2 H2WB 0.72(3) . ? O2 H2WA 0.83(3) . ? O3 H3WB 0.79(3) . ? O3 H3WA 0.84(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O1 86.93(9) . . ? O2 Mn1 N1 100.78(8) . . ? O1 Mn1 N1 89.20(5) . . ? O2 Mn1 O3 171.25(8) . . ? O1 Mn1 O3 88.78(9) . . ? N1 Mn1 O3 86.78(8) . . ? O2 Mn1 N2 87.82(8) . 2_665 ? O1 Mn1 N2 88.34(5) . 2_665 ? N1 Mn1 N2 170.92(7) . 2_665 ? O3 Mn1 N2 84.43(7) . 2_665 ? O2 Mn1 N6 89.54(7) . . ? O1 Mn1 N6 165.99(6) . . ? N1 Mn1 N6 78.14(7) . . ? O3 Mn1 N6 96.39(7) . . ? N2 Mn1 N6 105.08(7) 2_665 . ? N9 Mn2 N9 88.42(7) 7_776 2_765 ? N9 Mn2 N9 180.0 7_776 . ? N9 Mn2 N9 91.58(7) 2_765 . ? N9 Mn2 N9 88.42(7) 7_776 3_675 ? N9 Mn2 N9 91.58(7) 2_765 3_675 ? N9 Mn2 N9 91.58(7) . 3_675 ? N9 Mn2 N9 91.58(7) 7_776 9_656 ? N9 Mn2 N9 88.42(7) 2_765 9_656 ? N9 Mn2 N9 88.42(7) . 9_656 ? N9 Mn2 N9 180.0 3_675 9_656 ? N9 Mn2 N9 91.58(7) 7_776 8_566 ? N9 Mn2 N9 180.00(8) 2_765 8_566 ? N9 Mn2 N9 88.42(7) . 8_566 ? N9 Mn2 N9 88.42(7) 3_675 8_566 ? N9 Mn2 N9 91.58(7) 9_656 8_566 ? N1 C1 N4 112.5(2) . . ? N1 C1 N5 126.2(2) . . ? N4 C1 N5 121.3(2) . . ? N9 C2 N6 112.9(2) . . ? N9 C2 N5 121.9(2) . . ? N6 C2 N5 125.1(2) . . ? C1 N1 N2 103.9(2) . . ? C1 N1 Mn1 133.27(17) . . ? N2 N1 Mn1 122.79(15) . . ? N3 N2 N1 109.5(2) . . ? N3 N2 Mn1 129.16(16) . 3_565 ? N1 N2 Mn1 121.09(15) . 3_565 ? N2 N3 N4 110.2(2) . . ? C1 N4 N3 104.0(2) . . ? C1 N5 C2 126.1(2) . . ? C1 N5 H5N 116.5(17) . . ? C2 N5 H5N 117.4(16) . . ? C2 N9 N8 103.78(19) . . ? C2 N9 Mn2 135.79(17) . . ? N8 N9 Mn2 115.11(15) . . ? N7 N8 N9 110.2(2) . . ? N8 N7 N6 109.6(2) . . ? C2 N6 N7 103.5(2) . . ? C2 N6 Mn1 130.61(17) . . ? N7 N6 Mn1 125.51(15) . . ? Mn1 O1 Mn1 116.16(5) 2_665 . ? Mn1 O1 Mn1 116.16(5) 2_665 3_565 ? Mn1 O1 Mn1 116.16(5) . 3_565 ? Mn1 O1 H1 101.45(7) 2_665 . ? Mn1 O1 H1 101.45(7) . . ? Mn1 O1 H1 101.45(7) 3_565 . ? Mn1 O2 H2WB 108(3) . . ? Mn1 O2 H2WA 113(2) . . ? H2WB O2 H2WA 105(3) . . ? Mn1 O3 H3WB 108(2) . . ? Mn1 O3 H3WA 109(2) . . ? H3WB O3 H3WA 119(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 N1 N2 0.8(3) . . . . ? N5 C1 N1 N2 -179.5(2) . . . . ? N4 C1 N1 Mn1 178.40(17) . . . . ? N5 C1 N1 Mn1 -1.9(4) . . . . ? O2 Mn1 N1 C1 89.7(2) . . . . ? O1 Mn1 N1 C1 176.4(2) . . . . ? O3 Mn1 N1 C1 -94.8(2) . . . . ? N2 Mn1 N1 C1 -109.3(5) 2_665 . . . ? N6 Mn1 N1 C1 2.4(2) . . . . ? O2 Mn1 N1 N2 -93.09(18) . . . . ? O1 Mn1 N1 N2 -6.36(19) . . . . ? O3 Mn1 N1 N2 82.46(18) . . . . ? N2 Mn1 N1 N2 67.9(5) 2_665 . . . ? N6 Mn1 N1 N2 179.68(19) . . . . ? C1 N1 N2 N3 -0.4(3) . . . . ? Mn1 N1 N2 N3 -178.37(16) . . . . ? C1 N1 N2 Mn1 174.13(16) . . . 3_565 ? Mn1 N1 N2 Mn1 -3.8(2) . . . 3_565 ? N1 N2 N3 N4 -0.1(3) . . . . ? Mn1 N2 N3 N4 -174.04(16) 3_565 . . . ? N1 C1 N4 N3 -0.8(3) . . . . ? N5 C1 N4 N3 179.4(2) . . . . ? N2 N3 N4 C1 0.5(3) . . . . ? N1 C1 N5 C2 3.6(5) . . . . ? N4 C1 N5 C2 -176.7(3) . . . . ? N9 C2 N5 C1 173.9(2) . . . . ? N6 C2 N5 C1 -8.1(5) . . . . ? N6 C2 N9 N8 -1.9(3) . . . . ? N5 C2 N9 N8 176.3(2) . . . . ? N6 C2 N9 Mn2 149.61(18) . . . . ? N5 C2 N9 Mn2 -32.2(4) . . . . ? N9 Mn2 N9 C2 -117(100) 7_776 . . . ? N9 Mn2 N9 C2 66.1(3) 2_765 . . . ? N9 Mn2 N9 C2 157.7(2) 3_675 . . . ? N9 Mn2 N9 C2 -22.3(2) 9_656 . . . ? N9 Mn2 N9 C2 -113.9(3) 8_566 . . . ? N9 Mn2 N9 N8 32(100) 7_776 . . . ? N9 Mn2 N9 N8 -144.70(14) 2_765 . . . ? N9 Mn2 N9 N8 -53.07(19) 3_675 . . . ? N9 Mn2 N9 N8 126.93(19) 9_656 . . . ? N9 Mn2 N9 N8 35.30(14) 8_566 . . . ? C2 N9 N8 N7 1.5(3) . . . . ? Mn2 N9 N8 N7 -156.95(16) . . . . ? N9 N8 N7 N6 -0.6(3) . . . . ? N9 C2 N6 N7 1.5(3) . . . . ? N5 C2 N6 N7 -176.6(2) . . . . ? N9 C2 N6 Mn1 -171.48(15) . . . . ? N5 C2 N6 Mn1 10.4(4) . . . . ? N8 N7 N6 C2 -0.5(3) . . . . ? N8 N7 N6 Mn1 172.97(16) . . . . ? O2 Mn1 N6 C2 -107.6(2) . . . . ? O1 Mn1 N6 C2 -32.3(5) . . . . ? N1 Mn1 N6 C2 -6.5(2) . . . . ? O3 Mn1 N6 C2 78.9(2) . . . . ? N2 Mn1 N6 C2 164.8(2) 2_665 . . . ? O2 Mn1 N6 N7 80.76(19) . . . . ? O1 Mn1 N6 N7 156.1(3) . . . . ? N1 Mn1 N6 N7 -178.1(2) . . . . ? O3 Mn1 N6 N7 -92.79(19) . . . . ? N2 Mn1 N6 N7 -6.9(2) 2_665 . . . ? O2 Mn1 O1 Mn1 -103.05(12) . . . 2_665 ? N1 Mn1 O1 Mn1 156.12(12) . . . 2_665 ? O3 Mn1 O1 Mn1 69.33(12) . . . 2_665 ? N2 Mn1 O1 Mn1 -15.14(12) 2_665 . . 2_665 ? N6 Mn1 O1 Mn1 -178.7(3) . . . 2_665 ? O2 Mn1 O1 Mn1 114.91(12) . . . 3_565 ? N1 Mn1 O1 Mn1 14.08(12) . . . 3_565 ? O3 Mn1 O1 Mn1 -72.72(12) . . . 3_565 ? N2 Mn1 O1 Mn1 -157.18(12) 2_665 . . 3_565 ? N6 Mn1 O1 Mn1 39.3(4) . . . 3_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5N N8 0.799(15) 2.126(15) 2.914(3) 169(2) 2_765 O2 H2WB N7 0.72(3) 2.14(3) 2.796(3) 153(3) 5_675 O2 H2WA N3 0.83(3) 1.97(3) 2.788(3) 174(3) 6_665 O3 H3WB O3 0.79(3) 2.22(3) 2.885(3) 141(3) 3_565 O3 H3WA N4 0.84(3) 1.90(3) 2.717(3) 165(3) 8_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.471 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.067 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 682403' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H32 Cd7 N54 O14' _chemical_formula_weight 1943.72 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P-3c1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' _cell_length_a 14.6130(3) _cell_length_b 14.6130(3) _cell_length_c 13.6080(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2516.54(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12297 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1860 _exptl_absorpt_coefficient_mu 3.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5195 _exptl_absorpt_correction_T_max 0.7137 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 26176 _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1915 _reflns_number_gt 1352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0230P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1915 _refine_ls_number_parameters 148 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0447 _refine_ls_wR_factor_gt 0.0412 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.499277(17) 0.802344(17) 0.349804(18) 0.02661(8) Uani 1 1 d . . . Cd2 Cd 1.0000 1.0000 0.5000 0.02308(14) Uani 1 6 d S . . N1 N 0.55354(18) 0.68008(18) 0.3652(2) 0.0288(6) Uani 1 1 d . . . N2 N 0.48564(19) 0.57404(19) 0.36280(19) 0.0294(6) Uani 1 1 d . . . N3 N 0.53835(19) 0.5247(2) 0.3730(2) 0.0351(7) Uani 1 1 d . . . N4 N 0.6420(2) 0.59501(19) 0.3824(2) 0.0334(7) Uani 1 1 d . . . N5 N 0.74282(19) 0.78060(19) 0.3847(2) 0.0317(7) Uani 1 1 d D . . H5N H 0.7983(19) 0.778(3) 0.391(3) 0.047 Uiso 1 1 d D . . N6 N 0.68432(18) 0.90792(19) 0.36791(19) 0.0272(6) Uani 1 1 d . . . N7 N 0.73908(19) 1.01578(19) 0.3724(2) 0.0318(7) Uani 1 1 d . . . N8 N 0.83767(19) 1.04881(19) 0.3910(2) 0.0310(6) Uani 1 1 d . . . N9 N 0.85267(17) 0.96512(19) 0.4017(2) 0.0274(6) Uani 1 1 d . . . C1 C 0.6480(2) 0.6887(2) 0.3774(2) 0.0254(7) Uani 1 1 d . . . C2 C 0.7570(2) 0.8808(2) 0.3856(2) 0.0252(7) Uani 1 1 d . . . O1 O 0.3333 0.6667 0.3124(3) 0.0243(8) Uani 1 3 d SD . . H1 H 0.3333 0.6667 0.2549(15) 0.036 Uiso 1 3 d SD . . O2 O 0.51881(18) 0.83828(18) 0.18249(18) 0.0327(6) Uani 1 1 d . . . H2WB H 0.581(3) 0.877(3) 0.166(3) 0.049 Uiso 1 1 d . . . H2WA H 0.492(3) 0.868(3) 0.167(3) 0.049 Uiso 1 1 d . . . O3 O 0.4554(2) 0.77156(19) 0.5172(2) 0.0382(6) Uani 1 1 d . . . H3WB H 0.453(3) 0.722(3) 0.537(3) 0.057 Uiso 1 1 d . . . H3WA H 0.504(3) 0.817(3) 0.550(3) 0.057 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 Cd1 0.01824(13) 0.02145(13) 0.04066(16) 0.00089(10) -0.00051(10) 0.01032(10) Cd2 0.01567(17) 0.01567(17) 0.0379(4) 0.000 0.000 0.00784(9) N1 0.0183(13) 0.0217(14) 0.0456(18) -0.0029(12) -0.0019(12) 0.0094(12) N2 0.0227(14) 0.0210(13) 0.0425(18) -0.0017(12) -0.0015(12) 0.0093(11) N3 0.0273(15) 0.0238(14) 0.053(2) -0.0033(13) -0.0063(13) 0.0121(13) N4 0.0241(15) 0.0218(14) 0.054(2) -0.0036(13) -0.0069(13) 0.0110(12) N5 0.0142(13) 0.0207(14) 0.061(2) -0.0045(13) -0.0050(13) 0.0093(12) N6 0.0183(13) 0.0186(13) 0.0409(18) 0.0026(12) -0.0033(12) 0.0064(11) N7 0.0234(14) 0.0245(14) 0.0465(19) 0.0038(13) -0.0033(12) 0.0112(12) N8 0.0207(14) 0.0214(14) 0.0492(19) 0.0053(13) -0.0036(13) 0.0091(12) N9 0.0162(13) 0.0215(13) 0.0429(18) 0.0006(12) -0.0042(11) 0.0082(11) C1 0.0203(16) 0.0203(16) 0.036(2) -0.0031(14) -0.0027(14) 0.0103(14) C2 0.0197(16) 0.0224(16) 0.033(2) 0.0003(14) -0.0007(13) 0.0104(14) O1 0.0210(11) 0.0210(11) 0.031(2) 0.000 0.000 0.0105(6) O2 0.0228(12) 0.0309(13) 0.0442(16) 0.0046(11) 0.0014(11) 0.0133(11) O3 0.0399(15) 0.0281(14) 0.0453(18) -0.0018(12) -0.0036(12) 0.0161(12) _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 Cd1 O1 2.2941(8) . ? Cd1 N1 2.298(2) . ? Cd1 O2 2.322(2) . ? Cd1 N2 2.332(2) 2_665 ? Cd1 O3 2.349(3) . ? Cd1 N6 2.362(2) . ? Cd2 N9 2.364(2) . ? Cd2 N9 2.364(2) 8_566 ? Cd2 N9 2.364(2) 2_765 ? Cd2 N9 2.364(2) 7_776 ? Cd2 N9 2.364(2) 9_656 ? Cd2 N9 2.364(2) 3_675 ? N1 C1 1.333(4) . ? N1 N2 1.360(3) . ? N2 N3 1.299(3) . ? N2 Cd1 2.332(2) 3_565 ? N3 N4 1.345(3) . ? N4 C1 1.329(4) . ? N5 C1 1.368(4) . ? N5 C2 1.372(4) . ? N5 H5N 0.831(18) . ? N6 C2 1.329(4) . ? N6 N7 1.366(3) . ? N7 N8 1.295(3) . ? N8 N9 1.354(3) . ? N9 C2 1.341(3) . ? O1 Cd1 2.2941(8) 2_665 ? O1 Cd1 2.2941(8) 3_565 ? O1 H1 0.783(19) . ? O2 H2WB 0.83(4) . ? O2 H2WA 0.74(4) . ? O3 H3WB 0.76(4) . ? O3 H3WA 0.82(4) . ? 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 Cd1 N1 88.56(6) . . ? O1 Cd1 O2 86.27(11) . . ? N1 Cd1 O2 102.35(9) . . ? O1 Cd1 N2 87.68(6) . 2_665 ? N1 Cd1 N2 168.68(9) . 2_665 ? O2 Cd1 N2 88.06(9) . 2_665 ? O1 Cd1 O3 88.88(11) . . ? N1 Cd1 O3 86.00(9) . . ? O2 Cd1 O3 170.21(8) . . ? N2 Cd1 O3 83.25(9) 2_665 . ? O1 Cd1 N6 163.27(7) . . ? N1 Cd1 N6 76.76(8) . . ? O2 Cd1 N6 89.05(8) . . ? N2 Cd1 N6 108.22(8) 2_665 . ? O3 Cd1 N6 97.92(9) . . ? N9 Cd2 N9 88.89(9) . 8_566 ? N9 Cd2 N9 91.11(9) . 2_765 ? N9 Cd2 N9 180.00(11) 8_566 2_765 ? N9 Cd2 N9 180.000(1) . 7_776 ? N9 Cd2 N9 91.11(9) 8_566 7_776 ? N9 Cd2 N9 88.89(9) 2_765 7_776 ? N9 Cd2 N9 88.89(9) . 9_656 ? N9 Cd2 N9 91.11(9) 8_566 9_656 ? N9 Cd2 N9 88.89(9) 2_765 9_656 ? N9 Cd2 N9 91.11(9) 7_776 9_656 ? N9 Cd2 N9 91.11(9) . 3_675 ? N9 Cd2 N9 88.89(9) 8_566 3_675 ? N9 Cd2 N9 91.11(9) 2_765 3_675 ? N9 Cd2 N9 88.89(9) 7_776 3_675 ? N9 Cd2 N9 180.0 9_656 3_675 ? C1 N1 N2 104.0(2) . . ? C1 N1 Cd1 133.0(2) . . ? N2 N1 Cd1 123.02(17) . . ? N3 N2 N1 109.4(2) . . ? N3 N2 Cd1 127.79(19) . 3_565 ? N1 N2 Cd1 122.73(18) . 3_565 ? N2 N3 N4 109.9(2) . . ? C1 N4 N3 104.6(2) . . ? C1 N5 C2 125.9(3) . . ? C1 N5 H5N 120(3) . . ? C2 N5 H5N 114(3) . . ? C2 N6 N7 104.0(2) . . ? C2 N6 Cd1 130.47(19) . . ? N7 N6 Cd1 125.23(17) . . ? N8 N7 N6 109.8(2) . . ? N7 N8 N9 109.7(2) . . ? C2 N9 N8 104.3(2) . . ? C2 N9 Cd2 135.1(2) . . ? N8 N9 Cd2 114.03(17) . . ? N4 C1 N1 112.1(3) . . ? N4 C1 N5 121.4(3) . . ? N1 C1 N5 126.5(3) . . ? N6 C2 N9 112.1(2) . . ? N6 C2 N5 126.9(3) . . ? N9 C2 N5 121.0(3) . . ? Cd1 O1 Cd1 115.22(6) 2_665 . ? Cd1 O1 Cd1 115.22(6) 2_665 3_565 ? Cd1 O1 Cd1 115.22(6) . 3_565 ? Cd1 O1 H1 102.83(9) 2_665 . ? Cd1 O1 H1 102.83(9) . . ? Cd1 O1 H1 102.83(9) 3_565 . ? Cd1 O2 H2WB 113(2) . . ? Cd1 O2 H2WA 112(3) . . ? H2WB O2 H2WA 104(4) . . ? Cd1 O3 H3WB 114(3) . . ? Cd1 O3 H3WA 110(3) . . ? H3WB O3 H3WA 101(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 O1 Cd1 N1 C1 171.9(3) . . . . ? O2 Cd1 N1 C1 86.0(3) . . . . ? N2 Cd1 N1 C1 -117.5(4) 2_665 . . . ? O3 Cd1 N1 C1 -99.1(3) . . . . ? N6 Cd1 N1 C1 0.0(3) . . . . ? O1 Cd1 N1 N2 -8.0(2) . . . . ? O2 Cd1 N1 N2 -93.8(2) . . . . ? N2 Cd1 N1 N2 62.7(5) 2_665 . . . ? O3 Cd1 N1 N2 81.0(2) . . . . ? N6 Cd1 N1 N2 -179.9(2) . . . . ? C1 N1 N2 N3 0.0(3) . . . . ? Cd1 N1 N2 N3 179.9(2) . . . . ? C1 N1 N2 Cd1 177.3(2) . . . 3_565 ? Cd1 N1 N2 Cd1 -2.8(3) . . . 3_565 ? N1 N2 N3 N4 0.0(4) . . . . ? Cd1 N2 N3 N4 -177.15(19) 3_565 . . . ? N2 N3 N4 C1 0.1(3) . . . . ? O1 Cd1 N6 C2 -33.9(5) . . . . ? N1 Cd1 N6 C2 -4.7(3) . . . . ? O2 Cd1 N6 C2 -107.6(3) . . . . ? N2 Cd1 N6 C2 164.8(3) 2_665 . . . ? O3 Cd1 N6 C2 79.3(3) . . . . ? O1 Cd1 N6 N7 153.7(3) . . . . ? N1 Cd1 N6 N7 -177.1(2) . . . . ? O2 Cd1 N6 N7 80.0(2) . . . . ? N2 Cd1 N6 N7 -7.6(3) 2_665 . . . ? O3 Cd1 N6 N7 -93.1(2) . . . . ? C2 N6 N7 N8 0.4(3) . . . . ? Cd1 N6 N7 N8 174.5(2) . . . . ? N6 N7 N8 N9 -1.3(4) . . . . ? N7 N8 N9 C2 1.6(3) . . . . ? N7 N8 N9 Cd2 -154.7(2) . . . . ? N9 Cd2 N9 C2 -111.4(3) 8_566 . . . ? N9 Cd2 N9 C2 68.6(3) 2_765 . . . ? N9 Cd2 N9 C2 -129(100) 7_776 . . . ? N9 Cd2 N9 C2 -20.2(3) 9_656 . . . ? N9 Cd2 N9 C2 159.8(3) 3_675 . . . ? N9 Cd2 N9 N8 35.00(17) 8_566 . . . ? N9 Cd2 N9 N8 -145.00(17) 2_765 . . . ? N9 Cd2 N9 N8 18(100) 7_776 . . . ? N9 Cd2 N9 N8 126.1(2) 9_656 . . . ? N9 Cd2 N9 N8 -53.9(2) 3_675 . . . ? N3 N4 C1 N1 -0.1(4) . . . . ? N3 N4 C1 N5 179.7(3) . . . . ? N2 N1 C1 N4 0.1(4) . . . . ? Cd1 N1 C1 N4 -179.8(2) . . . . ? N2 N1 C1 N5 -179.7(3) . . . . ? Cd1 N1 C1 N5 0.4(5) . . . . ? C2 N5 C1 N4 -176.4(3) . . . . ? C2 N5 C1 N1 3.3(5) . . . . ? N7 N6 C2 N9 0.6(4) . . . . ? Cd1 N6 C2 N9 -173.0(2) . . . . ? N7 N6 C2 N5 -176.8(3) . . . . ? Cd1 N6 C2 N5 9.6(5) . . . . ? N8 N9 C2 N6 -1.3(4) . . . . ? Cd2 N9 C2 N6 147.2(2) . . . . ? N8 N9 C2 N5 176.2(3) . . . . ? Cd2 N9 C2 N5 -35.2(5) . . . . ? C1 N5 C2 N6 -8.6(5) . . . . ? C1 N5 C2 N9 174.2(3) . . . . ? N1 Cd1 O1 Cd1 153.27(15) . . . 2_665 ? O2 Cd1 O1 Cd1 -104.25(14) . . . 2_665 ? N2 Cd1 O1 Cd1 -16.04(14) 2_665 . . 2_665 ? O3 Cd1 O1 Cd1 67.25(14) . . . 2_665 ? N6 Cd1 O1 Cd1 -178.3(3) . . . 2_665 ? N1 Cd1 O1 Cd1 15.35(14) . . . 3_565 ? O2 Cd1 O1 Cd1 117.83(14) . . . 3_565 ? N2 Cd1 O1 Cd1 -153.97(15) 2_665 . . 3_565 ? O3 Cd1 O1 Cd1 -70.68(14) . . . 3_565 ? N6 Cd1 O1 Cd1 43.8(5) . . . 3_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5N N8 0.831(18) 2.163(19) 2.988(3) 172(3) 2_765 O2 H2WB N7 0.83(4) 1.94(4) 2.768(3) 171(3) 5_675 O2 H2WA N3 0.74(4) 2.07(4) 2.786(3) 163(4) 6_665 O3 H3WB O3 0.76(4) 2.36(4) 2.896(4) 128(4) 3_565 O3 H3WA N4 0.82(4) 1.98(4) 2.766(4) 160(4) 8_566 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.395 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.109 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 634263' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H30 F2 Mn7 N54 O12' _chemical_formula_weight 1545.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-3c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' _cell_length_a 14.355(3) _cell_length_b 14.355(3) _cell_length_c 13.705(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2445.7(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7936 _cell_measurement_theta_min 2.838 _cell_measurement_theta_max 28.186 _exptl_crystal_description polyhedral _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.099 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1538 _exptl_absorpt_coefficient_mu 1.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9203 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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_% 2.5 _diffrn_reflns_number 12451 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.32 _reflns_number_total 1946 _reflns_number_gt 1805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0370P)^2^+1.1459P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1946 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.498837(18) 0.798906(18) 0.350261(18) 0.01866(10) Uani 1 1 d . . . Mn2 Mn 1.0000 1.0000 0.5000 0.01790(14) Uani 1 6 d S . . C1 C 0.64483(12) 0.68498(12) 0.37779(12) 0.0190(3) Uani 1 1 d . . . C2 C 0.75676(12) 0.87964(12) 0.38760(12) 0.0201(3) Uani 1 1 d . . . N1 N 0.54953(10) 0.67752(10) 0.36241(11) 0.0210(3) Uani 1 1 d . . . N2 N 0.47921(10) 0.56995(10) 0.35968(10) 0.0222(3) Uani 1 1 d . . . N3 N 0.53109(11) 0.51818(11) 0.37203(12) 0.0270(3) Uani 1 1 d . . . N4 N 0.63658(11) 0.58852(11) 0.38367(12) 0.0256(3) Uani 1 1 d . . . N5 N 0.74193(11) 0.77780(11) 0.38708(13) 0.0260(3) Uani 1 1 d . . . H5N H 0.7947(19) 0.770(2) 0.3956(18) 0.040(6) Uiso 1 1 d . . . N6 N 0.68202(10) 0.90666(10) 0.36844(11) 0.0220(3) Uani 1 1 d . . . N7 N 0.73707(11) 1.01645(11) 0.37269(12) 0.0262(3) Uani 1 1 d . . . N8 N 0.83721(11) 1.05059(11) 0.39380(12) 0.0249(3) Uani 1 1 d . . . N9 N 0.85341(10) 0.96591(10) 0.40585(11) 0.0224(3) Uani 1 1 d . . . O2 O 0.51634(10) 0.82929(11) 0.19364(10) 0.0260(3) Uani 1 1 d . . . H2WB H 0.580(2) 0.869(2) 0.1733(18) 0.043(7) Uiso 1 1 d . . . H2WA H 0.489(2) 0.865(2) 0.175(2) 0.055(8) Uiso 1 1 d . . . O3 O 0.45997(12) 0.77267(12) 0.50875(11) 0.0296(3) Uani 1 1 d . . . H3WB H 0.446(2) 0.720(3) 0.527(3) 0.069(10) Uiso 1 1 d . . . H3WA H 0.502(2) 0.818(2) 0.545(2) 0.041(7) Uiso 1 1 d . . . F F 0.3333 0.6667 0.33125(12) 0.0213(3) Uani 1 3 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.01338(13) 0.01522(14) 0.02820(17) 0.00041(9) -0.00022(9) 0.00778(10) Mn2 0.01173(17) 0.01173(17) 0.0302(3) 0.000 0.000 0.00587(8) C1 0.0162(7) 0.0167(7) 0.0251(8) -0.0027(6) -0.0022(6) 0.0091(6) C2 0.0132(7) 0.0173(7) 0.0281(8) 0.0004(6) -0.0006(6) 0.0062(6) N1 0.0135(6) 0.0155(6) 0.0329(8) -0.0021(5) -0.0012(5) 0.0065(5) N2 0.0166(6) 0.0158(6) 0.0326(8) -0.0026(5) -0.0023(5) 0.0069(5) N3 0.0206(7) 0.0172(6) 0.0426(9) -0.0035(6) -0.0061(6) 0.0091(5) N4 0.0192(6) 0.0166(6) 0.0419(9) -0.0034(6) -0.0062(6) 0.0096(5) N5 0.0123(6) 0.0168(6) 0.0500(10) -0.0033(6) -0.0051(6) 0.0080(5) N6 0.0155(6) 0.0152(6) 0.0338(8) 0.0018(5) -0.0032(5) 0.0066(5) N7 0.0195(7) 0.0163(6) 0.0407(9) 0.0023(6) -0.0053(6) 0.0074(5) N8 0.0175(6) 0.0163(6) 0.0388(9) 0.0035(6) -0.0037(6) 0.0070(5) N9 0.0143(6) 0.0155(6) 0.0354(8) 0.0009(5) -0.0027(5) 0.0060(5) O2 0.0215(6) 0.0272(6) 0.0317(7) 0.0037(5) 0.0030(5) 0.0139(5) O3 0.0348(7) 0.0214(6) 0.0294(7) -0.0022(6) -0.0035(6) 0.0117(6) F 0.0156(5) 0.0156(5) 0.0327(9) 0.000 0.000 0.0078(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 Mn1 O2 2.1798(16) . ? Mn1 F 2.1922(5) . ? Mn1 N1 2.2049(14) . ? Mn1 O3 2.2273(17) . ? Mn1 N2 2.2506(14) 2_665 ? Mn1 N6 2.3025(14) . ? Mn2 N9 2.3028(14) 7_776 ? Mn2 N9 2.3028(14) . ? Mn2 N9 2.3028(14) 2_765 ? Mn2 N9 2.3028(14) 8_566 ? Mn2 N9 2.3028(14) 3_675 ? Mn2 N9 2.3028(14) 9_656 ? C1 N4 1.332(2) . ? C1 N1 1.3344(19) . ? C1 N5 1.370(2) . ? C2 N6 1.3367(19) . ? C2 N9 1.3427(19) . ? C2 N5 1.368(2) . ? N1 N2 1.3586(18) . ? N2 N3 1.2997(19) . ? N2 Mn1 2.2506(14) 3_565 ? N3 N4 1.3450(19) . ? N5 H5N 0.83(2) . ? N6 N7 1.3660(18) . ? N7 N8 1.2983(19) . ? N8 N9 1.3570(19) . ? O2 H2WB 0.84(3) . ? O2 H2WA 0.83(3) . ? O3 H3WB 0.73(4) . ? O3 H3WA 0.80(3) . ? F Mn1 2.1922(5) 2_665 ? F Mn1 2.1922(5) 3_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 F 91.31(6) . . ? O2 Mn1 N1 100.48(5) . . ? F Mn1 N1 88.15(3) . . ? O2 Mn1 O3 171.20(5) . . ? F Mn1 O3 84.15(6) . . ? N1 Mn1 O3 86.93(5) . . ? O2 Mn1 N2 87.87(5) . 2_665 ? F Mn1 N2 87.10(4) . 2_665 ? N1 Mn1 N2 170.48(5) . 2_665 ? O3 Mn1 N2 84.38(5) . 2_665 ? O2 Mn1 N6 89.63(5) . . ? F Mn1 N6 166.84(3) . . ? N1 Mn1 N6 78.78(5) . . ? O3 Mn1 N6 96.51(6) . . ? N2 Mn1 N6 106.05(5) 2_665 . ? N9 Mn2 N9 180.0 7_776 . ? N9 Mn2 N9 88.34(6) 7_776 2_765 ? N9 Mn2 N9 91.66(6) . 2_765 ? N9 Mn2 N9 91.66(6) 7_776 8_566 ? N9 Mn2 N9 88.34(6) . 8_566 ? N9 Mn2 N9 180.00(6) 2_765 8_566 ? N9 Mn2 N9 88.34(6) 7_776 3_675 ? N9 Mn2 N9 91.66(6) . 3_675 ? N9 Mn2 N9 91.66(6) 2_765 3_675 ? N9 Mn2 N9 88.34(6) 8_566 3_675 ? N9 Mn2 N9 91.66(6) 7_776 9_656 ? N9 Mn2 N9 88.34(6) . 9_656 ? N9 Mn2 N9 88.34(6) 2_765 9_656 ? N9 Mn2 N9 91.66(6) 8_566 9_656 ? N9 Mn2 N9 180.0 3_675 9_656 ? N4 C1 N1 111.80(13) . . ? N4 C1 N5 121.59(14) . . ? N1 C1 N5 126.61(14) . . ? N6 C2 N9 112.22(14) . . ? N6 C2 N5 126.19(14) . . ? N9 C2 N5 121.57(14) . . ? C1 N1 N2 104.18(12) . . ? C1 N1 Mn1 132.74(10) . . ? N2 N1 Mn1 123.01(10) . . ? N3 N2 N1 109.50(12) . . ? N3 N2 Mn1 127.75(10) . 3_565 ? N1 N2 Mn1 122.47(10) . 3_565 ? N2 N3 N4 109.75(13) . . ? C1 N4 N3 104.77(13) . . ? C2 N5 C1 125.37(13) . . ? C2 N5 H5N 118.8(17) . . ? C1 N5 H5N 115.8(17) . . ? C2 N6 N7 103.95(12) . . ? C2 N6 Mn1 129.72(10) . . ? N7 N6 Mn1 125.96(10) . . ? N8 N7 N6 109.74(12) . . ? N7 N8 N9 110.01(12) . . ? C2 N9 N8 104.04(12) . . ? C2 N9 Mn2 135.51(11) . . ? N8 N9 Mn2 115.18(10) . . ? Mn1 O2 H2WB 115.9(17) . . ? Mn1 O2 H2WA 112.8(19) . . ? H2WB O2 H2WA 100(2) . . ? Mn1 O3 H3WB 116(3) . . ? Mn1 O3 H3WA 116.8(19) . . ? H3WB O3 H3WA 109(3) . . ? Mn1 F Mn1 118.608(18) 2_665 . ? Mn1 F Mn1 118.608(18) 2_665 3_565 ? Mn1 F Mn1 118.608(18) . 3_565 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 N1 N2 0.56(19) . . . . ? N5 C1 N1 N2 -179.43(17) . . . . ? N4 C1 N1 Mn1 177.38(12) . . . . ? N5 C1 N1 Mn1 -2.6(3) . . . . ? O2 Mn1 N1 C1 90.41(16) . . . . ? F Mn1 N1 C1 -178.61(16) . . . . ? O3 Mn1 N1 C1 -94.37(16) . . . . ? N2 Mn1 N1 C1 -118.5(3) 2_665 . . . ? N6 Mn1 N1 C1 2.90(15) . . . . ? O2 Mn1 N1 N2 -93.27(13) . . . . ? F Mn1 N1 N2 -2.28(13) . . . . ? O3 Mn1 N1 N2 81.96(13) . . . . ? N2 Mn1 N1 N2 57.8(3) 2_665 . . . ? N6 Mn1 N1 N2 179.22(14) . . . . ? C1 N1 N2 N3 -0.47(18) . . . . ? Mn1 N1 N2 N3 -177.69(11) . . . . ? C1 N1 N2 Mn1 173.91(11) . . . 3_565 ? Mn1 N1 N2 Mn1 -3.30(18) . . . 3_565 ? N1 N2 N3 N4 0.2(2) . . . . ? Mn1 N2 N3 N4 -173.78(11) 3_565 . . . ? N1 C1 N4 N3 -0.4(2) . . . . ? N5 C1 N4 N3 179.56(16) . . . . ? N2 N3 N4 C1 0.1(2) . . . . ? N6 C2 N5 C1 -8.0(3) . . . . ? N9 C2 N5 C1 173.89(17) . . . . ? N4 C1 N5 C2 -176.03(17) . . . . ? N1 C1 N5 C2 3.9(3) . . . . ? N9 C2 N6 N7 1.66(19) . . . . ? N5 C2 N6 N7 -176.61(17) . . . . ? N9 C2 N6 Mn1 -171.60(12) . . . . ? N5 C2 N6 Mn1 10.1(3) . . . . ? O2 Mn1 N6 C2 -107.15(15) . . . . ? F Mn1 N6 C2 -13.0(4) . . . . ? N1 Mn1 N6 C2 -6.38(15) . . . . ? O3 Mn1 N6 C2 79.17(15) . . . . ? N2 Mn1 N6 C2 165.18(14) 2_665 . . . ? O2 Mn1 N6 N7 80.95(14) . . . . ? F Mn1 N6 N7 175.1(2) . . . . ? N1 Mn1 N6 N7 -178.29(15) . . . . ? O3 Mn1 N6 N7 -92.74(14) . . . . ? N2 Mn1 N6 N7 -6.73(15) 2_665 . . . ? C2 N6 N7 N8 -0.50(19) . . . . ? Mn1 N6 N7 N8 173.10(12) . . . . ? N6 N7 N8 N9 -0.8(2) . . . . ? N6 C2 N9 N8 -2.1(2) . . . . ? N5 C2 N9 N8 176.25(16) . . . . ? N6 C2 N9 Mn2 149.58(13) . . . . ? N5 C2 N9 Mn2 -32.1(3) . . . . ? N7 N8 N9 C2 1.7(2) . . . . ? N7 N8 N9 Mn2 -156.72(12) . . . . ? N9 Mn2 N9 C2 -91(100) 7_776 . . . ? N9 Mn2 N9 C2 65.7(2) 2_765 . . . ? N9 Mn2 N9 C2 -114.3(2) 8_566 . . . ? N9 Mn2 N9 C2 157.44(15) 3_675 . . . ? N9 Mn2 N9 C2 -22.56(15) 9_656 . . . ? N9 Mn2 N9 N8 59(100) 7_776 . . . ? N9 Mn2 N9 N8 -144.82(10) 2_765 . . . ? N9 Mn2 N9 N8 35.18(10) 8_566 . . . ? N9 Mn2 N9 N8 -53.11(14) 3_675 . . . ? N9 Mn2 N9 N8 126.89(14) 9_656 . . . ? O2 Mn1 F Mn1 -95.77(8) . . . 2_665 ? N1 Mn1 F Mn1 163.78(8) . . . 2_665 ? O3 Mn1 F Mn1 76.68(8) . . . 2_665 ? N2 Mn1 F Mn1 -7.97(8) 2_665 . . 2_665 ? N6 Mn1 F Mn1 170.3(2) . . . 2_665 ? O2 Mn1 F Mn1 107.49(8) . . . 3_565 ? N1 Mn1 F Mn1 7.04(8) . . . 3_565 ? O3 Mn1 F Mn1 -80.06(8) . . . 3_565 ? N2 Mn1 F Mn1 -164.70(8) 2_665 . . 3_565 ? N6 Mn1 F Mn1 13.5(3) . . . 3_565 ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.449 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.114 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 682404' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H8 Mn N9 O3.50' _chemical_formula_weight 269.11 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' N N 0.0061 0.0033 '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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 10.2789(9) _cell_length_b 24.033(2) _cell_length_c 7.4222(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1833.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8168 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.950 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.456 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6691 _exptl_absorpt_correction_T_max 0.8680 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 11478 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4201 _reflns_number_gt 4051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0268P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0126(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.011(10) _refine_ls_number_reflns 4201 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0487 _refine_ls_wR_factor_gt 0.0483 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn -0.00283(2) 0.662684(9) 0.02527(3) 0.01660(7) Uani 1 1 d . . . Mn2 Mn 0.36375(2) 0.436187(9) 0.52248(4) 0.01735(7) Uani 1 1 d . . . C1 C 0.30611(14) 0.63369(6) 0.0308(2) 0.0195(3) Uani 1 1 d . . . C2 C 0.26892(14) 0.73284(6) 0.0162(2) 0.0182(3) Uani 1 1 d . . . C3 C 0.49154(15) 0.31219(6) 0.4848(2) 0.0197(3) Uani 1 1 d . . . C4 C 0.65456(15) 0.38337(6) 0.5456(2) 0.0188(3) Uani 1 1 d . . . N1 N 0.18456(13) 0.61733(5) 0.0641(2) 0.0211(3) Uani 1 1 d . . . N2 N 0.19506(14) 0.56233(6) 0.1039(2) 0.0259(3) Uani 1 1 d . . . N3 N 0.31587(15) 0.54783(6) 0.0903(2) 0.0281(4) Uani 1 1 d . . . N4 N 0.39098(13) 0.59193(6) 0.0440(3) 0.0272(3) Uani 1 1 d . . . N5 N 0.34392(13) 0.68688(6) -0.0109(2) 0.0285(4) Uani 1 1 d . . . H5 H 0.424(2) 0.6917(8) -0.028(3) 0.035(6) Uiso 1 1 d . . . N6 N 0.14026(12) 0.73248(5) 0.0343(2) 0.0229(3) Uani 1 1 d . . . N7 N 0.10803(13) 0.78645(6) 0.0595(3) 0.0294(4) Uani 1 1 d . . . N8 N 0.21163(13) 0.81708(6) 0.0539(3) 0.0295(4) Uani 1 1 d . . . N9 N 0.31706(12) 0.78445(5) 0.0265(2) 0.0220(3) Uani 1 1 d . . . N10 N 0.38972(13) 0.34597(5) 0.4706(2) 0.0229(3) Uani 1 1 d . . . N11 N 0.28780(14) 0.31110(6) 0.4398(2) 0.0283(4) Uani 1 1 d . . . N12 N 0.32836(14) 0.26028(6) 0.4375(2) 0.0303(4) Uani 1 1 d . . . N13 N 0.45904(13) 0.25915(6) 0.4656(2) 0.0276(3) Uani 1 1 d . . . N14 N 0.61673(13) 0.32934(6) 0.5174(3) 0.0278(4) Uani 1 1 d . . . H14 H 0.6670(19) 0.3068(8) 0.528(3) 0.026(5) Uiso 1 1 d . . . N15 N 0.58226(12) 0.42887(5) 0.5244(2) 0.0181(3) Uani 1 1 d . . . N16 N 0.66432(13) 0.47135(6) 0.56559(19) 0.0203(3) Uani 1 1 d . . . N17 N 0.77824(14) 0.45170(6) 0.6083(2) 0.0237(3) Uani 1 1 d . . . N18 N 0.77573(14) 0.39571(6) 0.5980(2) 0.0231(3) Uani 1 1 d . . . O1 O -0.04045(15) 0.67034(7) 0.30741(19) 0.0298(3) Uani 1 1 d . . . H1WB H -0.013(3) 0.6934(11) 0.359(4) 0.049(8) Uiso 1 1 d . . . H1WA H -0.122(3) 0.6689(12) 0.345(4) 0.072(9) Uiso 1 1 d . . . O2 O -0.10653(13) 0.58362(5) 0.0277(2) 0.0308(3) Uani 1 1 d . . . H2WB H -0.065(2) 0.5565(10) -0.027(4) 0.051(7) Uiso 1 1 d . . . H2WA H -0.181(3) 0.5747(11) 0.072(4) 0.060(8) Uiso 1 1 d . . . O3 O 0.00493(14) 0.65379(5) -0.27210(16) 0.0232(3) Uani 1 1 d . . . H3WB H -0.003(3) 0.6838(11) -0.311(3) 0.049(8) Uiso 1 1 d . . . H3WA H 0.085(3) 0.6405(12) -0.322(4) 0.075(9) Uiso 1 1 d . . . O4 O 0.15483(12) 0.42724(6) 0.5285(2) 0.0315(3) Uani 1 1 d . . . H4WB H 0.104(2) 0.4497(9) 0.473(4) 0.045(7) Uiso 1 1 d . . . H4WA H 0.113(2) 0.4051(11) 0.579(4) 0.049(8) Uiso 1 1 d . . . O5 O 0.36040(15) 0.44579(6) 0.22765(17) 0.0276(3) Uani 1 1 d . . . H5WA H 0.355(2) 0.4797(10) 0.172(3) 0.045(7) Uiso 1 1 d . . . H5WB H 0.425(3) 0.4311(12) 0.190(4) 0.060(9) Uiso 1 1 d . . . O6 O 0.37292(16) 0.42161(6) 0.81352(18) 0.0301(3) Uani 1 1 d . . . H6WB H 0.456(3) 0.4204(13) 0.858(4) 0.083(11) Uiso 1 1 d . . . H6WA H 0.350(3) 0.3906(13) 0.846(4) 0.081(11) Uiso 1 1 d . . . O7 O 0.0000 0.5000 -0.1832(3) 0.0293(4) Uani 1 2 d S . . H7WB H 0.052(2) 0.5123(10) -0.251(3) 0.039(7) Uiso 1 1 d . . . O8 O 1.0000 0.5000 0.3267(3) 0.0315(4) Uani 1 2 d S . . H8WA H 0.951(2) 0.4817(10) 0.275(3) 0.046(8) 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 Mn1 0.01195(11) 0.01457(12) 0.02329(12) -0.00011(9) 0.00048(10) -0.00017(9) Mn2 0.01535(11) 0.01287(11) 0.02382(13) 0.00031(10) -0.00054(10) 0.00063(9) C1 0.0131(7) 0.0171(8) 0.0284(8) -0.0010(7) 0.0013(7) 0.0011(6) C2 0.0141(7) 0.0160(7) 0.0244(8) 0.0014(7) 0.0007(7) -0.0014(5) C3 0.0195(7) 0.0139(7) 0.0258(8) -0.0003(6) -0.0047(8) 0.0006(6) C4 0.0163(7) 0.0158(7) 0.0245(8) 0.0001(6) -0.0018(7) -0.0007(6) N1 0.0153(6) 0.0154(7) 0.0327(9) 0.0039(6) 0.0018(6) -0.0009(5) N2 0.0191(7) 0.0180(7) 0.0404(9) 0.0062(7) -0.0003(6) 0.0010(6) N3 0.0222(8) 0.0197(8) 0.0425(9) 0.0070(7) -0.0012(7) 0.0030(6) N4 0.0173(7) 0.0178(7) 0.0464(10) 0.0033(7) 0.0002(7) 0.0022(5) N5 0.0124(7) 0.0161(7) 0.0569(11) 0.0029(7) 0.0087(7) -0.0006(5) N6 0.0130(6) 0.0165(6) 0.0393(8) -0.0005(6) 0.0008(7) 0.0007(5) N7 0.0152(7) 0.0142(7) 0.0587(12) -0.0039(7) 0.0018(7) 0.0004(5) N8 0.0139(7) 0.0180(7) 0.0568(11) -0.0040(7) 0.0015(7) -0.0004(5) N9 0.0129(6) 0.0165(7) 0.0367(8) 0.0004(6) 0.0004(6) -0.0007(5) N10 0.0177(6) 0.0148(7) 0.0361(8) -0.0012(6) -0.0058(6) -0.0004(5) N11 0.0190(7) 0.0160(7) 0.0498(11) -0.0005(7) -0.0071(7) -0.0043(6) N12 0.0218(7) 0.0154(7) 0.0539(11) -0.0029(7) -0.0082(7) -0.0014(6) N13 0.0205(7) 0.0141(6) 0.0480(9) -0.0022(7) -0.0073(7) -0.0001(5) N14 0.0169(7) 0.0111(6) 0.0554(10) -0.0027(7) -0.0082(7) 0.0026(5) N15 0.0159(6) 0.0117(6) 0.0267(7) 0.0003(6) -0.0034(6) -0.0007(5) N16 0.0168(7) 0.0156(7) 0.0285(8) -0.0005(6) -0.0023(6) -0.0011(5) N17 0.0192(7) 0.0159(7) 0.0361(8) 0.0004(6) -0.0053(6) -0.0013(5) N18 0.0169(7) 0.0145(7) 0.0380(8) -0.0003(6) -0.0060(6) 0.0007(5) O1 0.0250(8) 0.0379(9) 0.0265(7) -0.0075(6) 0.0043(6) -0.0068(6) O2 0.0240(7) 0.0211(7) 0.0471(9) -0.0017(7) 0.0046(6) -0.0055(5) O3 0.0227(7) 0.0217(7) 0.0251(6) 0.0020(5) 0.0041(5) 0.0057(6) O4 0.0173(6) 0.0258(7) 0.0515(9) 0.0042(7) 0.0007(6) -0.0026(5) O5 0.0344(8) 0.0230(7) 0.0256(7) 0.0045(5) 0.0018(6) 0.0084(6) O6 0.0329(8) 0.0316(8) 0.0259(7) 0.0055(6) -0.0004(6) -0.0052(6) O7 0.0260(11) 0.0302(11) 0.0316(10) 0.000 0.000 -0.0041(9) O8 0.0284(11) 0.0320(11) 0.0341(10) 0.000 0.000 -0.0068(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.1375(14) . ? Mn1 O2 2.1789(12) . ? Mn1 O3 2.2189(12) . ? Mn1 N1 2.2320(14) . ? Mn1 N6 2.2319(13) . ? Mn1 N9 2.2781(13) 4_465 ? Mn2 O4 2.1586(13) . ? Mn2 O6 2.1904(14) . ? Mn2 O5 2.2007(13) . ? Mn2 N10 2.2184(13) . ? Mn2 N15 2.2530(13) . ? Mn2 N16 2.2635(14) 2_665 ? C1 N1 1.3330(19) . ? C1 N4 1.333(2) . ? C1 N5 1.372(2) . ? C2 N6 1.3293(19) . ? C2 N9 1.3375(19) . ? C2 N5 1.362(2) . ? C3 N13 1.325(2) . ? C3 N10 1.3287(19) . ? C3 N14 1.373(2) . ? C4 N15 1.3315(19) . ? C4 N18 1.338(2) . ? C4 N14 1.371(2) . ? N1 N2 1.359(2) . ? N2 N3 1.294(2) . ? N3 N4 1.356(2) . ? N5 H5 0.84(2) . ? N6 N7 1.3517(19) . ? N7 N8 1.2952(19) . ? N8 N9 1.3531(18) . ? N9 Mn1 2.2781(13) 4_565 ? N10 N11 1.3608(18) . ? N11 N12 1.291(2) . ? N12 N13 1.360(2) . ? N14 H14 0.75(2) . ? N15 N16 1.3593(18) . ? N16 N17 1.3019(19) . ? N16 Mn2 2.2635(14) 2_665 ? N17 N18 1.3481(19) . ? O1 H1WB 0.73(3) . ? O1 H1WA 0.88(3) . ? O2 H2WB 0.88(3) . ? O2 H2WA 0.86(3) . ? O3 H3WB 0.78(3) . ? O3 H3WA 0.96(3) . ? O4 H4WB 0.86(2) . ? O4 H4WA 0.78(3) . ? O5 H5WA 0.91(2) . ? O5 H5WB 0.80(3) . ? O6 H6WB 0.91(3) . ? O6 H6WA 0.82(3) . ? O7 H7WB 0.79(2) . ? O8 H8WA 0.78(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O2 88.77(6) . . ? O1 Mn1 O3 171.62(6) . . ? O2 Mn1 O3 86.65(6) . . ? O1 Mn1 N1 94.10(6) . . ? O2 Mn1 N1 89.73(5) . . ? O3 Mn1 N1 92.89(5) . . ? O1 Mn1 N6 91.44(6) . . ? O2 Mn1 N6 167.85(5) . . ? O3 Mn1 N6 94.51(5) . . ? N1 Mn1 N6 78.14(5) . . ? O1 Mn1 N9 88.30(6) . 4_465 ? O2 Mn1 N9 95.18(5) . 4_465 ? O3 Mn1 N9 85.13(6) . 4_465 ? N1 Mn1 N9 174.59(5) . 4_465 ? N6 Mn1 N9 96.98(5) . 4_465 ? O4 Mn2 O6 90.37(6) . . ? O4 Mn2 O5 90.89(6) . . ? O6 Mn2 O5 176.44(6) . . ? O4 Mn2 N10 91.49(5) . . ? O6 Mn2 N10 90.56(6) . . ? O5 Mn2 N10 86.09(6) . . ? O4 Mn2 N15 169.69(5) . . ? O6 Mn2 N15 86.47(6) . . ? O5 Mn2 N15 91.72(6) . . ? N10 Mn2 N15 78.74(5) . . ? O4 Mn2 N16 88.17(5) . 2_665 ? O6 Mn2 N16 91.33(5) . 2_665 ? O5 Mn2 N16 92.04(5) . 2_665 ? N10 Mn2 N16 178.09(6) . 2_665 ? N15 Mn2 N16 101.70(5) . 2_665 ? N1 C1 N4 112.18(14) . . ? N1 C1 N5 125.62(14) . . ? N4 C1 N5 122.19(14) . . ? N6 C2 N9 111.61(14) . . ? N6 C2 N5 124.95(14) . . ? N9 C2 N5 123.44(13) . . ? N13 C3 N10 112.36(14) . . ? N13 C3 N14 122.96(14) . . ? N10 C3 N14 124.67(14) . . ? N15 C4 N18 111.83(13) . . ? N15 C4 N14 126.95(14) . . ? N18 C4 N14 121.21(14) . . ? C1 N1 N2 104.65(13) . . ? C1 N1 Mn1 129.85(11) . . ? N2 N1 Mn1 124.87(10) . . ? N3 N2 N1 108.75(14) . . ? N2 N3 N4 110.84(14) . . ? C1 N4 N3 103.56(13) . . ? C2 N5 C1 124.20(13) . . ? C2 N5 H5 117.8(14) . . ? C1 N5 H5 116.0(14) . . ? C2 N6 N7 104.57(12) . . ? C2 N6 Mn1 131.11(11) . . ? N7 N6 Mn1 124.32(10) . . ? N8 N7 N6 109.85(13) . . ? N7 N8 N9 109.50(13) . . ? C2 N9 N8 104.46(12) . . ? C2 N9 Mn1 143.92(11) . 4_565 ? N8 N9 Mn1 110.67(9) . 4_565 ? C3 N10 N11 104.10(12) . . ? C3 N10 Mn2 132.69(10) . . ? N11 N10 Mn2 122.57(10) . . ? N12 N11 N10 109.65(13) . . ? N11 N12 N13 109.63(14) . . ? C3 N13 N12 104.26(13) . . ? C4 N14 C3 125.25(14) . . ? C4 N14 H14 118.0(15) . . ? C3 N14 H14 116.5(15) . . ? C4 N15 N16 104.12(12) . . ? C4 N15 Mn2 128.41(10) . . ? N16 N15 Mn2 124.15(10) . . ? N17 N16 N15 109.90(13) . . ? N17 N16 Mn2 120.35(10) . 2_665 ? N15 N16 Mn2 128.80(10) . 2_665 ? N16 N17 N18 109.33(13) . . ? C4 N18 N17 104.81(13) . . ? Mn1 O1 H1WB 121(2) . . ? Mn1 O1 H1WA 118(2) . . ? H1WB O1 H1WA 103(3) . . ? Mn1 O2 H2WB 114.1(16) . . ? Mn1 O2 H2WA 130.9(18) . . ? H2WB O2 H2WA 115(2) . . ? Mn1 O3 H3WB 105.7(18) . . ? Mn1 O3 H3WA 116.4(19) . . ? H3WB O3 H3WA 105(3) . . ? Mn2 O4 H4WB 122.4(15) . . ? Mn2 O4 H4WA 128.5(18) . . ? H4WB O4 H4WA 109(2) . . ? Mn2 O5 H5WA 122.9(15) . . ? Mn2 O5 H5WB 107(2) . . ? H5WA O5 H5WB 107(2) . . ? Mn2 O6 H6WB 114(2) . . ? Mn2 O6 H6WA 115(2) . . ? H6WB O6 H6WA 98(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.230 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.052 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 682405' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H8 N11 O0.50 Zn' _chemical_formula_weight 259.56 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' N N 0.0061 0.0033 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'pbam ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y, -z' '-x-1/2, y-1/2, z' 'x-1/2, -y-1/2, z' _cell_length_a 10.2897(16) _cell_length_b 23.812(4) _cell_length_c 7.0825(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1735.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1787 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 23.32 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 2.821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3982 _exptl_absorpt_correction_T_max 0.6023 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 9348 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1846 _reflns_number_gt 1352 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0941P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1846 _refine_ls_number_parameters 179 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1469 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.56496(7) 0.82928(3) 0.0000 0.0357(3) Uani 1 2 d S . . Zn2 Zn 0.63711(8) 0.56778(3) -0.5000 0.0359(3) Uani 1 2 d S . . C1 C 0.8284(6) 0.7693(3) 0.0000 0.0344(16) Uani 1 2 d S . . C2 C 0.8563(6) 0.8707(3) 0.0000 0.0333(16) Uani 1 2 d S . . C3 C 0.3681(7) 0.6196(3) -0.5000 0.0341(16) Uani 1 2 d S . . C4 C 0.5351(7) 0.6907(3) -0.5000 0.0376(18) Uani 1 2 d S . . N1 N 0.7007(5) 0.7665(2) 0.0000 0.0361(14) Uani 1 2 d S . . N2 N 0.6720(6) 0.7112(2) 0.0000 0.0449(16) Uani 1 2 d S . . N3 N 0.7769(6) 0.6831(2) 0.0000 0.0439(17) Uani 1 2 d S . . N4 N 0.8814(5) 0.7179(2) 0.0000 0.0379(15) Uani 1 2 d S . . N5 N 0.9034(6) 0.8165(2) 0.0000 0.0467(18) Uani 1 2 d S . . H5A H 0.9864 0.8122 0.0000 0.056 Uiso 1 2 calc SR . . N6 N 0.7318(5) 0.8837(2) 0.0000 0.0380(15) Uani 1 2 d S . . N7 N 0.7317(6) 0.9404(2) 0.0000 0.0501(18) Uani 1 2 d S . . N8 N 0.8488(7) 0.9587(3) 0.0000 0.0543(19) Uani 1 2 d S . . N9 N 0.9333(6) 0.9144(2) 0.0000 0.0435(16) Uani 1 2 d S . . N10 N 0.4425(5) 0.5745(2) -0.5000 0.0339(14) Uani 1 2 d S . . N11 N 0.3578(5) 0.5302(2) -0.5000 0.0376(15) Uani 1 2 d S . . N12 N 0.2426(6) 0.5504(3) -0.5000 0.0486(17) Uani 1 2 d S . . N13 N 0.2415(6) 0.6064(2) -0.5000 0.0446(16) Uani 1 2 d S . . N14 N 0.4088(6) 0.6744(2) -0.5000 0.0461(18) Uani 1 2 d S . . H14A H 0.3504 0.7002 -0.5000 0.055 Uiso 1 2 calc SR . . N15 N 0.6356(5) 0.6568(2) -0.5000 0.0411(16) Uani 1 2 d S . . N16 N 0.7433(6) 0.6899(3) -0.5000 0.0507(18) Uani 1 2 d S . . N17 N 0.7039(6) 0.7421(3) -0.5000 0.0550(19) Uani 1 2 d S . . N18 N 0.5726(7) 0.7450(3) -0.5000 0.0531(19) Uani 1 2 d S . . N19 N 0.7161(5) 0.56195(18) -0.7579(7) 0.0593(15) Uani 1 1 d . . . H19A H 0.7260 0.5259 -0.7883 0.089 Uiso 1 1 calc R . . H19B H 0.7932 0.5789 -0.7584 0.089 Uiso 1 1 calc R . . H19C H 0.6641 0.5785 -0.8417 0.089 Uiso 1 1 calc R . . N20 N 0.5118(4) 0.85806(19) 0.2587(6) 0.0509(13) Uani 1 1 d . . . H20A H 0.4391 0.8409 0.2951 0.076 Uiso 1 1 calc R . . H20B H 0.4982 0.8949 0.2529 0.076 Uiso 1 1 calc R . . H20C H 0.5748 0.8509 0.3414 0.076 Uiso 1 1 calc R . . O1 O 0.5000 1.0000 -0.125(2) 0.094(5) Uani 0.50 2 d SPD . . H1W H 0.543(13) 0.978(5) -0.054(6) 0.141 Uiso 0.50 1 d PD . . O2 O 0.0000 0.5000 -0.375(2) 0.097(5) Uani 0.50 2 d SPD . . H2W H 0.038(14) 0.524(4) -0.445(6) 0.145 Uiso 0.50 1 d PD . . 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 0.0209(4) 0.0227(5) 0.0635(6) 0.000 0.000 0.0024(3) Zn2 0.0225(5) 0.0252(5) 0.0599(6) 0.000 0.000 0.0009(3) C1 0.021(3) 0.022(3) 0.061(5) 0.000 0.000 -0.004(3) C2 0.019(3) 0.026(4) 0.054(5) 0.000 0.000 0.005(3) C3 0.024(4) 0.020(4) 0.058(5) 0.000 0.000 0.002(3) C4 0.029(4) 0.014(3) 0.070(5) 0.000 0.000 0.000(3) N1 0.021(3) 0.020(3) 0.068(4) 0.000 0.000 -0.001(2) N2 0.029(3) 0.022(3) 0.084(5) 0.000 0.000 0.000(3) N3 0.021(3) 0.019(3) 0.092(5) 0.000 0.000 -0.004(2) N4 0.023(3) 0.020(3) 0.071(4) 0.000 0.000 -0.001(2) N5 0.020(3) 0.019(3) 0.101(6) 0.000 0.000 0.002(2) N6 0.021(3) 0.023(3) 0.070(4) 0.000 0.000 0.002(2) N7 0.035(4) 0.019(3) 0.097(5) 0.000 0.000 0.008(3) N8 0.040(4) 0.020(3) 0.103(6) 0.000 0.000 0.008(3) N9 0.024(3) 0.022(3) 0.085(5) 0.000 0.000 -0.003(2) N10 0.025(3) 0.015(3) 0.062(4) 0.000 0.000 0.000(2) N11 0.020(3) 0.020(3) 0.072(4) 0.000 0.000 -0.003(2) N12 0.026(3) 0.026(3) 0.094(5) 0.000 0.000 -0.005(3) N13 0.021(3) 0.027(3) 0.087(5) 0.000 0.000 0.002(2) N14 0.024(3) 0.013(3) 0.101(6) 0.000 0.000 0.006(2) N15 0.022(3) 0.021(3) 0.080(5) 0.000 0.000 -0.003(2) N16 0.029(3) 0.023(3) 0.100(6) 0.000 0.000 -0.006(3) N17 0.036(4) 0.026(4) 0.103(6) 0.000 0.000 -0.009(3) N18 0.039(4) 0.020(3) 0.100(6) 0.000 0.000 -0.002(3) N19 0.072(4) 0.030(3) 0.076(4) -0.003(2) 0.023(3) -0.009(2) N20 0.032(3) 0.060(3) 0.061(3) -0.011(2) 0.001(2) -0.011(2) O1 0.069(10) 0.090(12) 0.123(13) 0.000 0.000 0.041(8) O2 0.058(9) 0.096(12) 0.137(14) 0.000 0.000 -0.040(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N20 2.031(4) . ? Zn1 N20 2.031(4) 6 ? Zn1 N1 2.045(5) . ? Zn1 N6 2.151(6) . ? Zn1 N4 2.198(6) 3_465 ? Zn2 N19 2.004(5) 6_554 ? Zn2 N19 2.004(5) . ? Zn2 N10 2.009(6) . ? Zn2 N15 2.119(6) . ? Zn2 N11 2.335(5) 5_664 ? C1 N1 1.316(8) . ? C1 N4 1.338(9) . ? C1 N5 1.364(9) . ? C2 N9 1.309(9) . ? C2 N6 1.318(8) . ? C2 N5 1.378(8) . ? C3 N10 1.320(8) . ? C3 N13 1.340(9) . ? C3 N14 1.371(8) . ? C4 N15 1.313(9) . ? C4 N18 1.349(9) . ? C4 N14 1.356(9) . ? N1 N2 1.349(8) . ? N2 N3 1.271(8) . ? N3 N4 1.359(8) . ? N4 Zn1 2.198(6) 3_565 ? N5 H5A 0.8600 . ? N6 N7 1.349(8) . ? N7 N8 1.282(9) . ? N8 N9 1.368(9) . ? N10 N11 1.367(7) . ? N11 N12 1.278(8) . ? N11 Zn2 2.335(5) 5_664 ? N12 N13 1.335(9) . ? N14 H14A 0.8600 . ? N15 N16 1.361(8) . ? N16 N17 1.307(9) . ? N17 N18 1.354(9) . ? N19 H19A 0.8900 . ? N19 H19B 0.8900 . ? N19 H19C 0.8900 . ? N20 H20A 0.8900 . ? N20 H20B 0.8900 . ? N20 H20C 0.8900 . ? O1 O2 1.772(19) 7_665 ? O1 O1 1.77(3) 5_675 ? O1 H1W 0.85(2) . ? O2 O1 1.772(19) 7_655 ? O2 O2 1.77(3) 5_564 ? O2 H2W 0.85(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N20 Zn1 N20 128.9(3) . 6 ? N20 Zn1 N1 115.49(14) . . ? N20 Zn1 N1 115.49(14) 6 . ? N20 Zn1 N6 90.66(14) . . ? N20 Zn1 N6 90.66(14) 6 . ? N1 Zn1 N6 84.0(2) . . ? N20 Zn1 N4 86.63(14) . 3_465 ? N20 Zn1 N4 86.63(14) 6 3_465 ? N1 Zn1 N4 102.3(2) . 3_465 ? N6 Zn1 N4 173.7(2) . 3_465 ? N19 Zn2 N19 131.4(3) 6_554 . ? N19 Zn2 N10 114.18(16) 6_554 . ? N19 Zn2 N10 114.18(16) . . ? N19 Zn2 N15 94.14(14) 6_554 . ? N19 Zn2 N15 94.14(14) . . ? N10 Zn2 N15 85.0(2) . . ? N19 Zn2 N11 85.51(14) 6_554 5_664 ? N19 Zn2 N11 85.51(14) . 5_664 ? N10 Zn2 N11 95.8(2) . 5_664 ? N15 Zn2 N11 179.1(2) . 5_664 ? N1 C1 N4 111.2(6) . . ? N1 C1 N5 127.3(6) . . ? N4 C1 N5 121.5(6) . . ? N9 C2 N6 113.7(6) . . ? N9 C2 N5 122.1(6) . . ? N6 C2 N5 124.2(6) . . ? N10 C3 N13 111.9(6) . . ? N10 C3 N14 126.8(6) . . ? N13 C3 N14 121.4(6) . . ? N15 C4 N18 111.4(6) . . ? N15 C4 N14 125.4(6) . . ? N18 C4 N14 123.2(6) . . ? C1 N1 N2 105.5(5) . . ? C1 N1 Zn1 130.2(5) . . ? N2 N1 Zn1 124.3(4) . . ? N3 N2 N1 109.2(6) . . ? N2 N3 N4 110.4(5) . . ? C1 N4 N3 103.7(5) . . ? C1 N4 Zn1 144.8(5) . 3_565 ? N3 N4 Zn1 111.5(4) . 3_565 ? C1 N5 C2 124.9(6) . . ? C1 N5 H5A 117.5 . . ? C2 N5 H5A 117.5 . . ? C2 N6 N7 103.6(6) . . ? C2 N6 Zn1 129.4(5) . . ? N7 N6 Zn1 127.0(4) . . ? N8 N7 N6 109.9(6) . . ? N7 N8 N9 109.5(6) . . ? C2 N9 N8 103.2(6) . . ? C3 N10 N11 104.9(6) . . ? C3 N10 Zn2 130.0(5) . . ? N11 N10 Zn2 125.1(4) . . ? N12 N11 N10 107.6(5) . . ? N12 N11 Zn2 113.3(4) . 5_664 ? N10 N11 Zn2 139.1(4) . 5_664 ? N11 N12 N13 112.5(6) . . ? N12 N13 C3 103.1(5) . . ? C4 N14 C3 124.4(6) . . ? C4 N14 H14A 117.8 . . ? C3 N14 H14A 117.8 . . ? C4 N15 N16 106.5(6) . . ? C4 N15 Zn2 128.5(5) . . ? N16 N15 Zn2 125.0(5) . . ? N17 N16 N15 107.4(6) . . ? N16 N17 N18 111.0(6) . . ? C4 N18 N17 103.7(6) . . ? Zn2 N19 H19A 109.5 . . ? Zn2 N19 H19B 109.5 . . ? H19A N19 H19B 109.5 . . ? Zn2 N19 H19C 109.5 . . ? H19A N19 H19C 109.5 . . ? H19B N19 H19C 109.5 . . ? Zn1 N20 H20A 109.5 . . ? Zn1 N20 H20B 109.5 . . ? H20A N20 H20B 109.5 . . ? Zn1 N20 H20C 109.5 . . ? H20A N20 H20C 109.5 . . ? H20B N20 H20C 109.5 . . ? O2 O1 O1 180.000(11) 7_665 5_675 ? O2 O1 H1W 126(2) 7_665 . ? O1 O1 H1W 54(2) 5_675 . ? O1 O2 O2 180.000(5) 7_655 5_564 ? O1 O2 H2W 126(2) 7_655 . ? O2 O2 H2W 54(2) 5_564 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A N2 0.86 1.99 2.842(8) 170.6 3_565 N14 H14A N17 0.86 2.04 2.897(8) 176.7 3_464 N19 H19A N8 0.89 2.32 3.071(7) 141.4 7_754 N20 H20C N13 0.89 2.29 3.037(7) 141.7 3_565 O1 H1W N7 0.85(2) 2.17(7) 2.913(8) 145(12) . O2 H2W N12 0.85(2) 2.23(11) 2.908(8) 137(14) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.864 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.118 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 682406' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H12 N18 O4 Zn' _chemical_formula_weight 441.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.560(2) _cell_length_b 15.038(5) _cell_length_c 6.879(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.334(4) _cell_angle_gamma 90.00 _cell_volume 746.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1271 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 25.56 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.965 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.714 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7256 _exptl_absorpt_correction_T_max 0.8473 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 4605 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1697 _reflns_number_gt 1324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0511P)^2^+1.8155P] 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 1697 _refine_ls_number_parameters 148 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 1.0000 1.0000 0.0000 0.0205(2) Uani 1 2 d S . . C1 C 1.2562(5) 0.8276(2) 0.0920(6) 0.0205(8) Uani 1 1 d . . . C2 C 1.4201(5) 0.9617(2) 0.2193(6) 0.0199(8) Uani 1 1 d . . . N1 N 1.0997(4) 0.8631(2) -0.0258(5) 0.0229(7) Uani 1 1 d . . . N2 N 0.9966(4) 0.7932(2) -0.1229(6) 0.0263(8) Uani 1 1 d . . . N3 N 1.0815(4) 0.7191(2) -0.0659(5) 0.0255(8) Uani 1 1 d . . . N4 N 1.2467(4) 0.7392(2) 0.0697(5) 0.0228(7) Uani 1 1 d . . . H4 H 1.329(7) 0.693(4) 0.134(8) 0.052(16) Uiso 1 1 d . . . N5 N 1.4030(5) 0.8705(2) 0.2168(6) 0.0269(8) Uani 1 1 d . . . H5 H 1.485(7) 0.837(3) 0.293(8) 0.038(14) Uiso 1 1 d . . . N6 N 1.2808(4) 1.0193(2) 0.1488(5) 0.0240(7) Uani 1 1 d . . . N7 N 1.3617(5) 1.0996(2) 0.1813(6) 0.0292(8) Uani 1 1 d . . . N8 N 1.5389(5) 1.0897(2) 0.2677(6) 0.0290(8) Uani 1 1 d . . . N9 N 1.5821(4) 1.0027(2) 0.2955(6) 0.0249(7) Uani 1 1 d . . . O1 O 0.9497(5) 0.9613(2) 0.2795(5) 0.0377(8) Uani 1 1 d D . . H1B H 0.841(4) 0.968(3) 0.280(9) 0.049(16) Uiso 1 1 d D . . H1A H 0.989(7) 0.911(2) 0.331(9) 0.08(2) Uiso 1 1 d D . . O2 O 1.6465(5) 0.7682(2) 0.5034(5) 0.0397(8) Uani 1 1 d D . . H2B H 1.696(7) 0.721(2) 0.492(8) 0.07(2) Uiso 1 1 d D . . H2A H 1.699(6) 0.796(4) 0.614(8) 0.13(4) Uiso 1 1 d 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 0.0137(3) 0.0179(3) 0.0267(4) 0.0007(3) 0.0013(2) 0.0012(2) C1 0.0210(18) 0.0161(17) 0.025(2) 0.0017(15) 0.0084(16) 0.0031(14) C2 0.0178(17) 0.0190(18) 0.022(2) 0.0013(15) 0.0050(15) 0.0015(15) N1 0.0180(15) 0.0203(16) 0.0273(18) -0.0005(13) 0.0021(13) 0.0023(13) N2 0.0210(16) 0.0216(16) 0.034(2) -0.0041(15) 0.0040(15) -0.0003(13) N3 0.0190(15) 0.0214(17) 0.034(2) -0.0060(14) 0.0041(15) -0.0009(13) N4 0.0180(15) 0.0158(15) 0.0335(19) -0.0025(14) 0.0059(14) 0.0012(13) N5 0.0211(16) 0.0157(16) 0.036(2) -0.0002(15) -0.0039(15) 0.0017(13) N6 0.0196(16) 0.0172(16) 0.0326(19) -0.0005(13) 0.0039(14) 0.0000(12) N7 0.0224(16) 0.0171(16) 0.044(2) -0.0032(15) 0.0035(16) -0.0023(13) N8 0.0233(17) 0.0202(17) 0.041(2) -0.0011(15) 0.0054(16) -0.0006(14) N9 0.0177(15) 0.0195(16) 0.036(2) -0.0022(14) 0.0057(15) -0.0013(13) O1 0.0332(17) 0.047(2) 0.0386(19) 0.0192(16) 0.0185(15) 0.0207(16) O2 0.0350(18) 0.0336(18) 0.040(2) -0.0097(15) -0.0041(15) 0.0129(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N6 2.085(3) . ? Zn1 N6 2.085(3) 3_775 ? Zn1 O1 2.149(3) . ? Zn1 O1 2.149(3) 3_775 ? Zn1 N1 2.217(3) 3_775 ? Zn1 N1 2.217(3) . ? C1 N1 1.330(5) . ? C1 N4 1.338(5) . ? C1 N5 1.348(5) . ? C2 N9 1.331(5) . ? C2 N6 1.338(5) . ? C2 N5 1.378(5) . ? N1 N2 1.360(5) . ? N2 N3 1.288(5) . ? N3 N4 1.352(5) . ? N4 H4 0.95(6) . ? N5 H5 0.85(5) . ? N6 N7 1.341(4) . ? N7 N8 1.302(5) . ? N8 N9 1.349(5) . ? O1 H1B 0.833(19) . ? O1 H1A 0.848(19) . ? O2 H2B 0.819(19) . ? O2 H2A 0.86(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Zn1 N6 180.000(1) . 3_775 ? N6 Zn1 O1 91.39(14) . . ? N6 Zn1 O1 88.61(14) 3_775 . ? N6 Zn1 O1 88.61(14) . 3_775 ? N6 Zn1 O1 91.39(14) 3_775 3_775 ? O1 Zn1 O1 180.00(18) . 3_775 ? N6 Zn1 N1 98.74(12) . 3_775 ? N6 Zn1 N1 81.26(12) 3_775 3_775 ? O1 Zn1 N1 91.44(13) . 3_775 ? O1 Zn1 N1 88.56(13) 3_775 3_775 ? N6 Zn1 N1 81.26(12) . . ? N6 Zn1 N1 98.74(12) 3_775 . ? O1 Zn1 N1 88.56(13) . . ? O1 Zn1 N1 91.44(13) 3_775 . ? N1 Zn1 N1 180.0 3_775 . ? N1 C1 N4 108.8(3) . . ? N1 C1 N5 127.6(3) . . ? N4 C1 N5 123.6(3) . . ? N9 C2 N6 112.1(3) . . ? N9 C2 N5 122.5(3) . . ? N6 C2 N5 125.4(3) . . ? C1 N1 N2 105.3(3) . . ? C1 N1 Zn1 125.8(3) . . ? N2 N1 Zn1 126.8(2) . . ? N3 N2 N1 111.0(3) . . ? N2 N3 N4 106.9(3) . . ? C1 N4 N3 108.0(3) . . ? C1 N4 H4 132(3) . . ? N3 N4 H4 120(3) . . ? C1 N5 C2 122.7(3) . . ? C1 N5 H5 115(3) . . ? C2 N5 H5 122(3) . . ? C2 N6 N7 104.6(3) . . ? C2 N6 Zn1 131.6(3) . . ? N7 N6 Zn1 123.7(2) . . ? N8 N7 N6 109.3(3) . . ? N7 N8 N9 110.4(3) . . ? C2 N9 N8 103.7(3) . . ? Zn1 O1 H1B 114(4) . . ? Zn1 O1 H1A 119(4) . . ? H1B O1 H1A 110(3) . . ? H2B O2 H2A 114(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4 N8 0.95(6) 1.86(6) 2.802(5) 171(5) 2_845 N5 H5 O2 0.85(5) 1.90(5) 2.735(5) 169(5) . O1 H1B N9 0.833(19) 2.05(2) 2.882(5) 172(5) 1_455 O1 H1A N3 0.848(19) 2.13(2) 2.974(5) 175(6) 4_576 O2 H2B N7 0.819(19) 2.15(3) 2.828(5) 140(4) 2_845 O2 H2A N7 0.86(2) 2.244(19) 2.957(5) 141(4) 3_876 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.925 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.111