# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Department of Chemistry, East China Normal University, Shanghai 200062, China. ; _publ_contact_author_email eqgao@chem.ecnu.edu.cn _publ_contact_author_fax 86-21-62233404 _publ_contact_author_phone 86-21-62233404 #TrackingRef 'Compound 1.cif' _publ_contact_author_name 'En-Qing Gao' _publ_author_name 'En-Qing Gao' data_Mn_1 _database_code_depnum_ccdc_archive 'CCDC 848910' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 Mn3 N22 O6, 4(H2 O)' _chemical_formula_sum 'C16 H24 Mn3 N22 O10' _chemical_formula_weight 849.39 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' Mn Mn 0.3368 0.7283 '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' _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 7.6829(17) _cell_length_b 10.533(2) _cell_length_c 11.055(2) _cell_angle_alpha 62.913(2) _cell_angle_beta 80.351(2) _cell_angle_gamma 85.288(2) _cell_volume 785.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2893 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 429 _exptl_absorpt_coefficient_mu 1.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_process_details 'SADABS(Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 3960 _diffrn_reflns_av_R_equivalents 0.0130 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2765 _reflns_number_gt 2434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.2596P] 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 2765 _refine_ls_number_parameters 235 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.70449(4) 0.84415(3) -0.24329(3) 0.02317(11) Uani 1 1 d . . . Mn2 Mn 0.5000 0.5000 0.0000 0.01937(12) Uani 1 2 d S . . C1 C 0.8488(3) 0.6224(2) 0.02276(19) 0.0218(4) Uani 1 1 d . . . C2 C 0.9604(3) 0.6083(2) 0.13042(19) 0.0235(4) Uani 1 1 d . . . H2B H 1.0763 0.5715 0.1116 0.028 Uiso 1 1 calc R . . H2A H 0.9756 0.7019 0.1238 0.028 Uiso 1 1 calc R . . C3 C 0.8315(3) 0.5647(2) 0.36323(19) 0.0226(4) Uani 1 1 d . . . H3A H 0.8538 0.6597 0.3379 0.027 Uiso 1 1 calc R . . C4 C 0.7506(3) 0.4789(2) 0.4941(2) 0.0238(4) Uani 1 1 d . . . C5 C 0.7106(3) 0.3392(2) 0.5269(2) 0.0325(5) Uani 1 1 d . . . H5A H 0.6501 0.2808 0.6129 0.039 Uiso 1 1 calc R . . C6 C 0.7607(3) 0.2881(2) 0.4323(2) 0.0327(5) Uani 1 1 d . . . H6A H 0.7354 0.1945 0.4544 0.039 Uiso 1 1 calc R . . C7 C 0.8482(3) 0.3750(2) 0.3048(2) 0.0272(5) Uani 1 1 d . . . H7A H 0.8865 0.3395 0.2416 0.033 Uiso 1 1 calc R . . C8 C 0.7114(3) 0.5344(2) 0.59648(19) 0.0234(4) Uani 1 1 d . . . O1 O 0.8795(2) 0.72893(16) -0.09018(14) 0.0327(4) Uani 1 1 d . . . O2 O 0.7447(2) 0.52419(15) 0.05382(15) 0.0326(4) Uani 1 1 d . . . O3 O 0.6833(2) 0.99438(17) -0.15246(17) 0.0391(4) Uani 1 1 d . . . H3C H 0.7837 1.0387 -0.1756 0.059 Uiso 1 1 d R . . H3B H 0.5908 1.0504 -0.1782 0.059 Uiso 1 1 d R . . O4 O 0.5857(2) 0.80700(18) 0.15024(17) 0.0448(4) Uani 1 1 d . . . H4A H 0.5089 0.7555 0.1568 0.067 Uiso 1 1 d R . . H4B H 0.5987 0.8613 0.0738 0.067 Uiso 1 1 d R . . O5 O 0.0225(3) 0.1089(2) 0.7720(2) 0.0560(5) Uani 1 1 d . . . H5B H 0.0748 0.0478 0.8520 0.084 Uiso 1 1 d R . . H5C H 0.0341 0.0876 0.7044 0.084 Uiso 1 1 d R . . N1 N 0.2382(3) 0.8764(3) -0.0498(3) 0.0579(7) Uani 1 1 d U . . N2 N 0.3505(3) 0.80560(19) -0.06993(19) 0.0311(4) Uani 1 1 d U . . N3 N 0.4698(2) 0.73375(17) -0.08836(18) 0.0294(4) Uani 1 1 d U . . N7 N 0.6267(2) 0.45854(18) 0.72322(17) 0.0271(4) Uani 1 1 d . . . N6 N 0.6250(2) 0.54369(18) 0.78304(16) 0.0263(4) Uani 1 1 d . . . N5 N 0.7051(2) 0.66435(19) 0.69586(17) 0.0279(4) Uani 1 1 d . . . N4 N 0.7620(3) 0.66163(19) 0.57567(17) 0.0296(4) Uani 1 1 d . . . N8 N 0.5000 1.0000 -0.5000 0.0404(7) Uani 1 2 d S . . N9 N 0.5359(4) 0.9777(2) -0.3941(2) 0.0590(7) Uani 1 1 d . . . N10 N 1.0000 1.0000 -0.5000 0.0315(6) Uani 1 2 d S . . N11 N 0.9465(3) 0.9470(2) -0.3828(2) 0.0460(5) Uani 1 1 d . . . N12 N 0.8784(2) 0.51227(17) 0.27178(15) 0.0212(4) 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 Mn1 0.0307(2) 0.02030(17) 0.01541(17) -0.00546(13) -0.00145(13) -0.00348(13) Mn2 0.0245(2) 0.0187(2) 0.0140(2) -0.00697(17) -0.00023(16) -0.00347(17) C1 0.0212(10) 0.0268(10) 0.0188(10) -0.0125(9) -0.0018(8) 0.0035(8) C2 0.0256(11) 0.0282(10) 0.0154(9) -0.0089(8) 0.0003(8) -0.0057(8) C3 0.0279(11) 0.0233(10) 0.0189(10) -0.0111(8) -0.0048(8) 0.0003(8) C4 0.0286(11) 0.0261(10) 0.0172(9) -0.0107(8) -0.0025(8) 0.0011(8) C5 0.0461(14) 0.0256(11) 0.0190(10) -0.0057(9) 0.0023(9) -0.0040(10) C6 0.0496(15) 0.0203(10) 0.0272(11) -0.0105(9) -0.0033(10) -0.0017(10) C7 0.0385(13) 0.0248(10) 0.0205(10) -0.0123(9) -0.0064(9) 0.0056(9) C8 0.0271(11) 0.0266(10) 0.0171(9) -0.0104(8) -0.0026(8) -0.0002(8) O1 0.0342(9) 0.0363(8) 0.0176(7) -0.0023(7) -0.0056(6) -0.0050(7) O2 0.0368(9) 0.0298(8) 0.0299(8) -0.0083(7) -0.0135(7) -0.0062(7) O3 0.0407(10) 0.0356(9) 0.0484(10) -0.0253(8) -0.0051(8) -0.0025(7) O4 0.0541(11) 0.0400(9) 0.0402(10) -0.0169(8) -0.0077(8) -0.0053(8) O5 0.0587(13) 0.0482(11) 0.0710(13) -0.0326(10) -0.0175(11) -0.0013(9) N1 0.0413(14) 0.0443(13) 0.0820(18) -0.0289(13) 0.0047(12) 0.0074(11) N2 0.0292(10) 0.0255(9) 0.0340(10) -0.0097(8) -0.0011(8) -0.0052(8) N3 0.0330(10) 0.0193(8) 0.0310(10) -0.0095(8) 0.0020(8) -0.0001(8) N7 0.0387(11) 0.0259(9) 0.0180(8) -0.0122(7) 0.0013(7) -0.0039(8) N6 0.0358(10) 0.0262(9) 0.0179(8) -0.0116(7) 0.0001(7) -0.0033(8) N5 0.0369(11) 0.0283(9) 0.0185(8) -0.0118(7) 0.0029(7) -0.0062(8) N4 0.0395(11) 0.0316(10) 0.0183(8) -0.0131(8) 0.0027(7) -0.0065(8) N8 0.0446(18) 0.0256(14) 0.0377(18) 0.0025(12) -0.0192(14) -0.0060(12) N9 0.0818(19) 0.0467(14) 0.0406(14) -0.0045(11) -0.0353(13) 0.0022(13) N10 0.0332(15) 0.0268(13) 0.0280(16) -0.0089(12) 0.0046(12) -0.0049(11) N11 0.0506(14) 0.0464(12) 0.0250(12) -0.0061(10) 0.0108(10) -0.0101(10) N12 0.0257(9) 0.0233(8) 0.0145(8) -0.0085(7) -0.0030(7) 0.0007(7) _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 N9 2.174(2) . ? Mn1 O1 2.1843(15) . ? Mn1 N11 2.204(2) . ? Mn1 O3 2.2109(16) 1 ? Mn1 O3 2.2109(16) . ? Mn1 N3 2.2434(18) . ? Mn1 N5 2.2797(18) 1_554 ? Mn2 O2 2.1320(15) 2_665 ? Mn2 O2 2.1320(15) . ? Mn2 N3 2.2049(17) 2_665 ? Mn2 N3 2.2049(17) . ? Mn2 N6 2.2765(17) 1_554 ? Mn2 N6 2.2765(17) 2_666 ? C1 O1 1.242(2) . ? C1 O2 1.245(2) . ? C1 C2 1.527(3) . ? C2 N12 1.482(2) . ? C2 H2B 0.9700 . ? C2 H2A 0.9700 . ? C3 N12 1.346(2) . ? C3 C4 1.377(3) . ? C3 H3A 0.9300 . ? C4 C5 1.393(3) . ? C4 C8 1.475(3) . ? C5 C6 1.370(3) . ? C5 H5A 0.9300 . ? C6 C7 1.373(3) . ? C6 H6A 0.9300 . ? C7 N12 1.351(3) . ? C7 H7A 0.9300 . ? C8 N4 1.332(3) . ? C8 N7 1.336(3) . ? O3 O3 0.000(4) 1 ? O3 H3C 0.8730 . ? O3 H3B 0.8836 . ? O4 H4A 0.8060 . ? O4 H4B 0.7697 . ? O5 H5B 0.9566 . ? O5 H5C 0.8624 . ? N1 N2 1.153(3) . ? N2 N3 1.191(3) . ? N7 N6 1.333(2) . ? N6 N5 1.318(2) . ? N6 Mn2 2.2765(17) 1_556 ? N5 N4 1.340(2) . ? N5 Mn1 2.2797(18) 1_556 ? N8 N9 1.161(2) 2_674 ? N8 N9 1.161(2) . ? N10 N11 1.1661(19) . ? N10 N11 1.1661(19) 2_774 ? 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 N9 Mn1 O1 174.33(8) . . ? N9 Mn1 N11 92.50(10) . . ? O1 Mn1 N11 85.51(7) . . ? N9 Mn1 O3 91.86(8) . 1 ? O1 Mn1 O3 82.91(6) . 1 ? N11 Mn1 O3 92.01(7) . 1 ? N9 Mn1 O3 91.86(8) . . ? O1 Mn1 O3 82.91(6) . . ? N11 Mn1 O3 92.01(7) . . ? O3 Mn1 O3 0.00(4) 1 . ? N9 Mn1 N3 91.51(9) . . ? O1 Mn1 N3 90.37(6) . . ? N11 Mn1 N3 175.75(8) . . ? O3 Mn1 N3 86.46(6) 1 . ? O3 Mn1 N3 86.46(6) . . ? N9 Mn1 N5 92.24(8) . 1_554 ? O1 Mn1 N5 93.24(6) . 1_554 ? N11 Mn1 N5 95.79(7) . 1_554 ? O3 Mn1 N5 171.02(6) 1 1_554 ? O3 Mn1 N5 171.02(6) . 1_554 ? N3 Mn1 N5 85.45(6) . 1_554 ? O2 Mn2 O2 180.00(9) 2_665 . ? O2 Mn2 N3 87.47(6) 2_665 2_665 ? O2 Mn2 N3 92.53(6) . 2_665 ? O2 Mn2 N3 92.53(6) 2_665 . ? O2 Mn2 N3 87.47(6) . . ? N3 Mn2 N3 180.0 2_665 . ? O2 Mn2 N6 87.33(6) 2_665 1_554 ? O2 Mn2 N6 92.67(6) . 1_554 ? N3 Mn2 N6 95.50(6) 2_665 1_554 ? N3 Mn2 N6 84.50(6) . 1_554 ? O2 Mn2 N6 92.67(6) 2_665 2_666 ? O2 Mn2 N6 87.33(6) . 2_666 ? N3 Mn2 N6 84.50(6) 2_665 2_666 ? N3 Mn2 N6 95.50(6) . 2_666 ? N6 Mn2 N6 180.0 1_554 2_666 ? O1 C1 O2 126.87(19) . . ? O1 C1 C2 115.43(18) . . ? O2 C1 C2 117.58(17) . . ? N12 C2 C1 112.11(16) . . ? N12 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? N12 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? H2B C2 H2A 107.9 . . ? N12 C3 C4 120.49(18) . . ? N12 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C3 C4 C5 118.43(18) . . ? C3 C4 C8 120.05(18) . . ? C5 C4 C8 121.50(18) . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 120.0(2) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? N12 C7 C6 119.56(19) . . ? N12 C7 H7A 120.2 . . ? C6 C7 H7A 120.2 . . ? N4 C8 N7 112.75(17) . . ? N4 C8 C4 124.28(18) . . ? N7 C8 C4 122.92(18) . . ? C1 O1 Mn1 129.27(14) . . ? C1 O2 Mn2 137.36(13) . . ? O3 O3 Mn1 0(10) 1 . ? O3 O3 H3C 0.0 1 . ? Mn1 O3 H3C 108.6 . . ? O3 O3 H3B 0.0 1 . ? Mn1 O3 H3B 108.4 . . ? H3C O3 H3B 114.9 . . ? H4A O4 H4B 104.0 . . ? H5B O5 H5C 119.1 . . ? N1 N2 N3 177.8(3) . . ? N2 N3 Mn2 130.66(15) . . ? N2 N3 Mn1 118.02(13) . . ? Mn2 N3 Mn1 111.27(8) . . ? N6 N7 C8 103.89(16) . . ? N5 N6 N7 109.89(15) . . ? N5 N6 Mn2 122.65(12) . 1_556 ? N7 N6 Mn2 127.44(13) . 1_556 ? N6 N5 N4 109.64(16) . . ? N6 N5 Mn1 119.49(12) . 1_556 ? N4 N5 Mn1 130.57(13) . 1_556 ? C8 N4 N5 103.83(16) . . ? N9 N8 N9 180.000(1) 2_674 . ? N8 N9 Mn1 141.9(2) . . ? N11 N10 N11 180.00(12) . 2_774 ? N10 N11 Mn1 139.27(17) . . ? C3 N12 C7 121.50(17) . . ? C3 N12 C2 119.27(16) . . ? C7 N12 C2 119.20(16) . . ? 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 C1 C2 N12 160.05(17) . . . . ? O2 C1 C2 N12 -23.6(3) . . . . ? N12 C3 C4 C5 -3.3(3) . . . . ? N12 C3 C4 C8 175.58(19) . . . . ? C3 C4 C5 C6 3.6(3) . . . . ? C8 C4 C5 C6 -175.2(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C5 C6 C7 N12 -2.5(4) . . . . ? C3 C4 C8 N4 -5.8(3) . . . . ? C5 C4 C8 N4 173.0(2) . . . . ? C3 C4 C8 N7 177.1(2) . . . . ? C5 C4 C8 N7 -4.1(3) . . . . ? O2 C1 O1 Mn1 31.0(3) . . . . ? C2 C1 O1 Mn1 -152.99(14) . . . . ? N9 Mn1 O1 C1 123.9(8) . . . . ? N11 Mn1 O1 C1 -166.47(19) . . . . ? O3 Mn1 O1 C1 100.94(18) 1 . . . ? O3 Mn1 O1 C1 100.94(18) . . . . ? N3 Mn1 O1 C1 14.55(18) . . . . ? N5 Mn1 O1 C1 -70.91(18) 1_554 . . . ? O1 C1 O2 Mn2 -32.2(3) . . . . ? C2 C1 O2 Mn2 151.94(16) . . . . ? O2 Mn2 O2 C1 -25(100) 2_665 . . . ? N3 Mn2 O2 C1 164.3(2) 2_665 . . . ? N3 Mn2 O2 C1 -15.7(2) . . . . ? N6 Mn2 O2 C1 68.6(2) 1_554 . . . ? N6 Mn2 O2 C1 -111.4(2) 2_666 . . . ? N9 Mn1 O3 O3 0.0(4) . . . 1 ? O1 Mn1 O3 O3 0.0(4) . . . 1 ? N11 Mn1 O3 O3 0.0(4) . . . 1 ? N3 Mn1 O3 O3 0.0(4) . . . 1 ? N5 Mn1 O3 O3 0.0(4) 1_554 . . 1 ? N1 N2 N3 Mn2 109(6) . . . . ? N1 N2 N3 Mn1 -74(6) . . . . ? O2 Mn2 N3 N2 52.0(2) 2_665 . . . ? O2 Mn2 N3 N2 -128.0(2) . . . . ? N3 Mn2 N3 N2 -68(100) 2_665 . . . ? N6 Mn2 N3 N2 139.1(2) 1_554 . . . ? N6 Mn2 N3 N2 -40.9(2) 2_666 . . . ? O2 Mn2 N3 Mn1 -125.17(8) 2_665 . . . ? O2 Mn2 N3 Mn1 54.83(8) . . . . ? N3 Mn2 N3 Mn1 114(100) 2_665 . . . ? N6 Mn2 N3 Mn1 -38.10(8) 1_554 . . . ? N6 Mn2 N3 Mn1 141.90(8) 2_666 . . . ? N9 Mn1 N3 N2 -48.12(18) . . . . ? O1 Mn1 N3 N2 126.53(17) . . . . ? N11 Mn1 N3 N2 112.6(10) . . . . ? O3 Mn1 N3 N2 43.65(17) 1 . . . ? O3 Mn1 N3 N2 43.65(17) . . . . ? N5 Mn1 N3 N2 -140.25(17) 1_554 . . . ? N9 Mn1 N3 Mn2 129.49(10) . . . . ? O1 Mn1 N3 Mn2 -55.86(8) . . . . ? N11 Mn1 N3 Mn2 -69.8(10) . . . . ? O3 Mn1 N3 Mn2 -138.74(9) 1 . . . ? O3 Mn1 N3 Mn2 -138.74(9) . . . . ? N5 Mn1 N3 Mn2 37.36(8) 1_554 . . . ? N4 C8 N7 N6 0.1(2) . . . . ? C4 C8 N7 N6 177.50(19) . . . . ? C8 N7 N6 N5 0.0(2) . . . . ? C8 N7 N6 Mn2 178.38(14) . . . 1_556 ? N7 N6 N5 N4 0.0(2) . . . . ? Mn2 N6 N5 N4 -178.55(14) 1_556 . . . ? N7 N6 N5 Mn1 174.27(14) . . . 1_556 ? Mn2 N6 N5 Mn1 -4.2(2) 1_556 . . 1_556 ? N7 C8 N4 N5 -0.1(2) . . . . ? C4 C8 N4 N5 -177.5(2) . . . . ? N6 N5 N4 C8 0.1(2) . . . . ? Mn1 N5 N4 C8 -173.37(15) 1_556 . . . ? N9 N8 N9 Mn1 -28(100) 2_674 . . . ? O1 Mn1 N9 N8 136.5(7) . . . . ? N11 Mn1 N9 N8 67.2(3) . . . . ? O3 Mn1 N9 N8 159.3(3) 1 . . . ? O3 Mn1 N9 N8 159.3(3) . . . . ? N3 Mn1 N9 N8 -114.2(3) . . . . ? N5 Mn1 N9 N8 -28.6(3) 1_554 . . . ? N11 N10 N11 Mn1 -163(100) 2_774 . . . ? N9 Mn1 N11 N10 -32.2(3) . . . . ? O1 Mn1 N11 N10 153.1(3) . . . . ? O3 Mn1 N11 N10 -124.1(2) 1 . . . ? O3 Mn1 N11 N10 -124.1(2) . . . . ? N3 Mn1 N11 N10 167.1(8) . . . . ? N5 Mn1 N11 N10 60.3(2) 1_554 . . . ? C4 C3 N12 C7 0.0(3) . . . . ? C4 C3 N12 C2 178.19(18) . . . . ? C6 C7 N12 C3 3.0(3) . . . . ? C6 C7 N12 C2 -175.2(2) . . . . ? C1 C2 N12 C3 -118.07(19) . . . . ? C1 C2 N12 C7 60.2(2) . . . . ? 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 O3 H3C O5 0.87 1.93 2.796(3) 170.6 1_664 O3 H3B O4 0.88 2.03 2.823(3) 148.1 2_675 O5 H5B N1 0.96 2.08 2.943(3) 149.7 1_546 O4 H4B O3 0.77 2.25 3.007(2) 168.9 1 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.310 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.064 # Attachment 'Compound 2.cif' data_Mn_2 _database_code_depnum_ccdc_archive 'CCDC 848911' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Mn3 N22 O10.50' _chemical_formula_sum 'C18 H24 Mn3 N22 O10.50' _chemical_formula_weight 881.41 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_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 13.10(2) _cell_length_b 19.77(3) _cell_length_c 14.05(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.448(17) _cell_angle_gamma 90.00 _cell_volume 3408(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2979 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 26.25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1780 _exptl_absorpt_coefficient_mu 1.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 0.889 _exptl_absorpt_process_details 'SADABS(Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9117 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3316 _reflns_number_gt 2356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1036P)^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 3316 _refine_ls_number_parameters 280 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1684 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.048 _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 0.71567(5) 0.41875(3) 0.58218(4) 0.0313(2) Uani 1 1 d . . . Mn2 Mn 0.7500 0.2500 0.5000 0.0274(3) Uani 1 2 d S . . O1 O 0.1577(3) 0.08190(15) 0.9183(2) 0.0404(8) Uani 1 1 d . . . O2 O 0.1766(2) 0.18657(16) 0.8684(2) 0.0393(7) Uani 1 1 d . . . O3 O 0.7653(3) 0.4241(2) 0.7460(3) 0.0575(10) Uani 1 1 d D A . H3D H 0.744(5) 0.435(3) 0.796(3) 0.086 Uiso 1 1 d D . . H3C H 0.834(2) 0.416(3) 0.781(4) 0.086 Uiso 1 1 d D . . O4 O 0.8382(3) 0.4947(2) 0.5786(4) 0.0644(12) Uani 0.50 1 d P A 1 O5 O 1.0000 0.5452(10) 0.7500 0.086(7) Uani 0.50 2 d SP B 1 O6 O 0.6334(5) 0.4449(2) 0.8533(4) 0.0884(15) Uani 1 1 d D . . H6A H 0.584(6) 0.413(3) 0.866(6) 0.133 Uiso 1 1 d D . . H6B H 0.634(7) 0.4828(14) 0.882(5) 0.133 Uiso 1 1 d D . . O7 O 0.9006(6) 0.4154(5) 0.3906(12) 0.147(7) Uani 0.50 1 d P . . N1 N 1.0251(4) 0.3521(3) 0.6457(4) 0.0838(18) Uani 1 1 d . A . N2 N 0.9316(3) 0.3444(2) 0.6194(3) 0.0491(11) Uani 1 1 d . . . N3 N 0.8348(3) 0.33756(19) 0.5909(3) 0.0369(9) Uani 1 1 d . A . N4 N 0.5029(3) 0.33198(19) 0.6094(3) 0.0348(8) Uani 1 1 d . . . N5 N 0.5932(3) 0.33399(18) 0.5840(2) 0.0320(8) Uani 1 1 d . A . N6 N 0.6140(3) 0.27316(19) 0.5591(3) 0.0349(8) Uani 1 1 d . A . N7 N 0.5401(3) 0.22972(18) 0.5679(3) 0.0375(8) Uani 1 1 d . . . N8 N 0.5000 0.5000 0.5000 0.0329(11) Uani 1 2 d S . . N9 N 0.5851(3) 0.4934(2) 0.5642(3) 0.0467(10) Uani 1 1 d . A . N10 N 0.2005(3) 0.18415(18) 0.6490(2) 0.0305(8) Uani 1 1 d . A . N11 N 0.8382(3) 0.4947(2) 0.5786(4) 0.0644(12) Uani 0.50 1 d PD A 2 N12' N 0.8635(17) 0.5039(12) 0.5075(15) 0.094(6) Uani 0.25 1 d PD A 2 N12 N 0.9061(15) 0.5120(11) 0.6628(15) 0.094(6) Uani 0.25 1 d PD . 2 N13' N 0.8941(15) 0.5164(11) 0.4370(11) 0.063(4) Uani 0.25 1 d PD A 2 N13 N 0.9915(19) 0.5288(18) 0.7250(15) 0.063(4) Uani 0.25 1 d PD . 2 C1 C 0.1591(3) 0.1253(2) 0.8528(3) 0.0304(9) Uani 1 1 d . . . C2 C 0.1347(4) 0.0996(2) 0.7453(3) 0.0343(10) Uani 1 1 d . . . H2A H 0.1983 0.0757 0.7427 0.041 Uiso 1 1 calc R . . H2B H 0.0756 0.0671 0.7301 0.041 Uiso 1 1 calc R . . C3 C 0.1040(3) 0.1529(2) 0.6640(3) 0.0357(10) Uani 1 1 d . . . H3A H 0.0580 0.1328 0.6005 0.043 Uiso 1 1 calc R . . H3B H 0.0622 0.1879 0.6820 0.043 Uiso 1 1 calc R . . C4 C 0.2531(4) 0.1479(2) 0.5996(3) 0.0394(10) Uani 1 1 d . . . H4A H 0.2287 0.1047 0.5762 0.047 Uiso 1 1 calc R . . C5 C 0.3422(4) 0.1739(2) 0.5833(3) 0.0421(11) Uani 1 1 d . A . H5A H 0.3783 0.1484 0.5493 0.051 Uiso 1 1 calc R . . C6 C 0.3793(3) 0.2388(2) 0.6177(3) 0.0316(9) Uani 1 1 d . . . C7 C 0.3220(3) 0.2746(2) 0.6675(3) 0.0342(10) Uani 1 1 d . A . H7A H 0.3440 0.3181 0.6909 0.041 Uiso 1 1 calc R . . C8 C 0.2339(3) 0.2467(2) 0.6824(3) 0.0335(9) Uani 1 1 d . . . H8A H 0.1965 0.2712 0.7162 0.040 Uiso 1 1 calc R A . C9 C 0.4732(3) 0.2669(2) 0.5981(3) 0.0313(9) Uani 1 1 d . A . 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 0.0287(4) 0.0303(4) 0.0355(4) -0.0014(3) 0.0120(3) 0.0025(3) Mn2 0.0257(5) 0.0259(5) 0.0338(5) 0.0021(3) 0.0146(3) 0.0028(3) O1 0.0531(19) 0.0358(19) 0.0353(15) 0.0000(13) 0.0193(14) -0.0085(14) O2 0.0469(18) 0.0342(19) 0.0357(15) -0.0053(13) 0.0132(13) -0.0057(14) O3 0.050(2) 0.081(3) 0.0391(17) -0.0049(17) 0.0120(15) 0.011(2) O4 0.044(2) 0.038(2) 0.096(3) -0.005(2) 0.005(2) -0.0097(18) O5 0.103(11) 0.049(11) 0.055(9) 0.000 -0.037(8) 0.000 O6 0.140(4) 0.051(3) 0.123(4) -0.023(3) 0.106(3) -0.026(3) O7 0.032(4) 0.107(8) 0.295(17) 0.147(10) 0.047(7) 0.017(5) N1 0.028(2) 0.119(5) 0.093(4) -0.034(3) 0.008(2) 0.004(3) N2 0.038(2) 0.048(3) 0.057(2) -0.014(2) 0.0120(18) 0.0033(19) N3 0.0240(18) 0.033(2) 0.049(2) -0.0032(16) 0.0081(15) 0.0038(14) N4 0.0300(18) 0.038(2) 0.0425(18) -0.0003(16) 0.0200(15) -0.0017(15) N5 0.0297(18) 0.033(2) 0.0367(17) -0.0030(15) 0.0161(14) 0.0009(15) N6 0.0327(19) 0.035(2) 0.0434(19) 0.0019(16) 0.0212(15) -0.0016(16) N7 0.037(2) 0.031(2) 0.051(2) -0.0033(17) 0.0244(16) -0.0043(16) N8 0.040(3) 0.025(3) 0.039(3) -0.006(2) 0.020(2) 0.005(2) N9 0.039(2) 0.049(3) 0.044(2) -0.0112(18) 0.0034(18) 0.0123(18) N10 0.0267(17) 0.033(2) 0.0336(17) 0.0003(15) 0.0132(13) -0.0028(14) N11 0.044(2) 0.038(2) 0.096(3) -0.005(2) 0.005(2) -0.0097(18) N12' 0.051(9) 0.061(11) 0.153(17) 0.030(11) 0.014(11) 0.005(8) N12 0.051(9) 0.061(11) 0.153(17) 0.030(11) 0.014(11) 0.005(8) N13' 0.069(10) 0.081(12) 0.050(8) 0.000(7) 0.037(8) -0.013(9) N13 0.069(10) 0.081(12) 0.050(8) 0.000(7) 0.037(8) -0.013(9) C1 0.029(2) 0.029(2) 0.036(2) -0.0029(18) 0.0143(16) -0.0043(17) C2 0.040(2) 0.029(2) 0.037(2) -0.0016(18) 0.0176(18) -0.0096(18) C3 0.029(2) 0.045(3) 0.034(2) -0.0033(19) 0.0136(17) -0.0094(19) C4 0.039(2) 0.033(3) 0.053(3) -0.006(2) 0.026(2) -0.005(2) C5 0.047(3) 0.035(3) 0.055(3) -0.009(2) 0.031(2) -0.003(2) C6 0.030(2) 0.034(2) 0.0313(19) 0.0012(17) 0.0116(16) 0.0002(17) C7 0.034(2) 0.028(2) 0.045(2) -0.0056(18) 0.0180(18) -0.0067(18) C8 0.033(2) 0.034(3) 0.038(2) -0.0021(18) 0.0179(17) 0.0026(18) C9 0.029(2) 0.035(3) 0.033(2) 0.0005(17) 0.0141(16) 0.0006(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 Mn1 O1 2.158(6) 8 ? Mn1 O3 2.165(6) . ? Mn1 N9 2.205(5) . ? Mn1 O4 2.210(5) . ? Mn1 N3 2.212(4) . ? Mn1 N5 2.326(4) . ? Mn2 O2 2.162(4) 2_656 ? Mn2 O2 2.162(4) 8 ? Mn2 N3 2.207(4) . ? Mn2 N3 2.207(4) 7_656 ? Mn2 N6 2.260(5) 7_656 ? Mn2 N6 2.260(5) . ? O1 C1 1.263(5) . ? O1 Mn1 2.158(6) 8_456 ? O2 C1 1.238(5) . ? O2 Mn2 2.162(4) 2_656 ? O3 H3D 0.86(2) . ? O3 H3C 0.87(2) . ? O6 H6A 0.968(17) . ? O6 H6B 0.852(18) . ? N1 N2 1.159(6) . ? N2 N3 1.196(5) . ? N4 C9 1.337(6) . ? N4 N5 1.349(5) . ? N5 N6 1.308(5) . ? N6 N7 1.331(5) . ? N7 C9 1.322(6) . ? N8 N9 1.171(4) . ? N8 N9 1.171(4) 5_666 ? N10 C8 1.340(6) . ? N10 C4 1.343(6) . ? N10 C3 1.486(5) . ? N12' N13' 1.217(15) . ? N12 N13 1.200(16) . ? N12 N13 1.71(3) 2_756 ? N13 N13 0.66(4) 2_756 ? N13 N12 1.71(3) 2_756 ? C1 C2 1.517(6) . ? C2 C3 1.503(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.365(6) . ? C4 H4A 0.9300 . ? C5 C6 1.397(6) . ? C5 H5A 0.9300 . ? C6 C7 1.385(6) . ? C6 C9 1.461(6) . ? C7 C8 1.360(6) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? 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 O3 176.19(13) 8 . ? O1 Mn1 N9 84.95(13) 8 . ? O3 Mn1 N9 91.24(14) . . ? O1 Mn1 O4 88.14(16) 8 . ? O3 Mn1 O4 92.30(18) . . ? N9 Mn1 O4 94.8(2) . . ? O1 Mn1 N3 91.92(13) 8 . ? O3 Mn1 N3 91.87(14) . . ? N9 Mn1 N3 174.67(13) . . ? O4 Mn1 N3 89.4(2) . . ? O1 Mn1 N5 91.19(12) 8 . ? O3 Mn1 N5 88.59(14) . . ? N9 Mn1 N5 88.5(2) . . ? O4 Mn1 N5 176.64(14) . . ? N3 Mn1 N5 87.30(19) . . ? O2 Mn2 O2 180.0 2_656 8 ? O2 Mn2 N3 88.62(18) 2_656 . ? O2 Mn2 N3 91.38(18) 8 . ? O2 Mn2 N3 91.38(18) 2_656 7_656 ? O2 Mn2 N3 88.62(18) 8 7_656 ? N3 Mn2 N3 180.00(12) . 7_656 ? O2 Mn2 N6 91.40(17) 2_656 7_656 ? O2 Mn2 N6 88.60(17) 8 7_656 ? N3 Mn2 N6 93.98(16) . 7_656 ? N3 Mn2 N6 86.02(16) 7_656 7_656 ? O2 Mn2 N6 88.60(17) 2_656 . ? O2 Mn2 N6 91.40(17) 8 . ? N3 Mn2 N6 86.02(16) . . ? N3 Mn2 N6 93.98(16) 7_656 . ? N6 Mn2 N6 180.000(1) 7_656 . ? C1 O1 Mn1 133.8(3) . 8_456 ? C1 O2 Mn2 135.9(3) . 2_656 ? Mn1 O3 H3D 144(4) . . ? Mn1 O3 H3C 117(4) . . ? H3D O3 H3C 98(4) . . ? H6A O6 H6B 113(4) . . ? N1 N2 N3 178.6(6) . . ? N2 N3 Mn2 122.9(3) . . ? N2 N3 Mn1 125.5(3) . . ? Mn2 N3 Mn1 109.52(17) . . ? C9 N4 N5 104.0(3) . . ? N6 N5 N4 109.1(3) . . ? N6 N5 Mn1 116.7(3) . . ? N4 N5 Mn1 134.1(3) . . ? N5 N6 N7 110.0(3) . . ? N5 N6 Mn2 123.3(3) . . ? N7 N6 Mn2 126.6(3) . . ? C9 N7 N6 104.8(4) . . ? N9 N8 N9 180.000(1) . 5_666 ? N8 N9 Mn1 130.9(3) . . ? C8 N10 C4 120.6(4) . . ? C8 N10 C3 121.5(4) . . ? C4 N10 C3 117.8(4) . . ? N13 N12 N13 16.9(19) . 2_756 ? N13 N13 N12 131(5) 2_756 . ? N13 N13 N12 32(3) 2_756 2_756 ? N12 N13 N12 148(3) . 2_756 ? O2 C1 O1 125.8(4) . . ? O2 C1 C2 117.7(4) . . ? O1 C1 C2 116.5(4) . . ? C3 C2 C1 115.4(4) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? N10 C3 C2 112.7(3) . . ? N10 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N10 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? N10 C4 C5 120.5(4) . . ? N10 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 120.2(4) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C7 C6 C5 117.3(4) . . ? C7 C6 C9 122.8(4) . . ? C5 C6 C9 119.9(4) . . ? C8 C7 C6 120.6(4) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? N10 C8 C7 120.8(4) . . ? N10 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? N7 C9 N4 112.0(4) . . ? N7 C9 C6 123.0(4) . . ? N4 C9 C6 124.9(4) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.974 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.106