# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Wen Dong' _publ_contact_author_email DW320@YAHOO.COM.CN _publ_section_title ; Syntheses, Structures and Properties of Seven H2BTA Coordinating 3d Metallic Complexes Containing Zero-, One-, Two-, and Three-Dimensional Frameworks (H2BTA = Bis(tetrazoly)amine ) ; loop_ _publ_author_name 'Wen Dong' 'Yang-Fan Guan' 'Bei-Shu Huang' 'Jiao-Min Lin' ; Zhao-Qing Liu ; 'Dong-Yao Wang' data_mn2 _database_code_depnum_ccdc_archive 'CCDC 659743' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C2 H7 Mn N9 O3), H2 O' _chemical_formula_sum 'C4 H16 Mn2 N18 O7' _chemical_formula_weight 538.23 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 orthorhombic _symmetry_space_group_name_H-M P21212 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 23.9993(19) _cell_length_b 10.2755(8) _cell_length_c 7.4265(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1831.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2453 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 27.580 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.201 _exptl_crystal_size_min 0.113 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.952 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.458 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_correction_T_max 0.848 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II area-detector diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 28926 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.58 _reflns_number_total 4245 _reflns_number_gt 4141 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SMART (Bruker, 2004)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material SHELXL-97 _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^)+(0.0415P)^2^+0.4997P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.035(11) _refine_ls_number_reflns 4245 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0211 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.162849(10) 1.00311(2) 0.02610(4) 0.01666(7) Uani 1 1 d . . . Mn2 Mn 0.063794(10) 0.36427(2) 0.52345(4) 0.01951(7) Uani 1 1 d . . . N1 N 0.11741(6) 0.81589(14) 0.0653(2) 0.0206(3) Uani 1 1 d . . . N2 N 0.06243(7) 0.80545(16) 0.1040(3) 0.0260(3) Uani 1 1 d . . . N3 N 0.04781(7) 0.68485(16) 0.0901(3) 0.0293(4) Uani 1 1 d . . . N4 N 0.09192(6) 0.60958(14) 0.0444(3) 0.0278(4) Uani 1 1 d . . . N5 N 0.18684(6) 0.65619(14) -0.0101(3) 0.0286(4) Uani 1 1 d . . . N6 N 0.28443(6) 0.68321(13) 0.0254(3) 0.0221(3) Uani 1 1 d . . . N7 N 0.31713(6) 0.78887(14) 0.0518(3) 0.0313(4) Uani 1 1 d . . . N8 N 0.28650(6) 0.89235(15) 0.0589(3) 0.0304(4) Uani 1 1 d . . . N9 N 0.23245(6) 0.86017(13) 0.0347(2) 0.0228(3) Uani 1 1 d . . . N10 N -0.15426(6) 0.61003(14) 0.4721(3) 0.0236(3) Uani 1 1 d . . . N11 N -0.18903(6) 0.71164(16) 0.4412(3) 0.0300(4) Uani 1 1 d . . . N12 N -0.23983(6) 0.67104(16) 0.4380(3) 0.0313(4) Uani 1 1 d . . . N13 N -0.24107(6) 0.54077(15) 0.4654(3) 0.0290(4) Uani 1 1 d . . . N14 N -0.17074(6) 0.38285(15) 0.5173(3) 0.0290(4) Uani 1 1 d . . . N15 N -0.10427(6) 0.22379(15) 0.5991(3) 0.0237(3) Uani 1 1 d . . . N16 N -0.04846(6) 0.22175(16) 0.6095(2) 0.0246(3) Uani 1 1 d . . . N17 N -0.02874(6) 0.33549(14) 0.5669(2) 0.0216(3) Uani 1 1 d . . . N18 N -0.07121(6) 0.41738(13) 0.5254(2) 0.0196(3) Uani 1 1 d . . . O1 O 0.05423(6) 0.36132(17) 0.2294(2) 0.0295(3) Uani 1 1 d . . . H3 H 0.0228(11) 0.360(3) 0.177(4) 0.037(7) Uiso 1 1 d . . . H4 H 0.070(2) 0.441(5) 0.190(7) 0.116(18) Uiso 1 1 d . . . O2 O 0.07797(7) 0.37339(17) 0.8142(2) 0.0334(3) Uani 1 1 d . . . H5 H 0.0786(18) 0.461(5) 0.859(6) 0.100(15) Uiso 1 1 d . . . O3 O 0.07291(6) 0.15482(13) 0.5296(3) 0.0327(3) Uani 1 1 d . . . H7 H 0.0966(12) 0.113(3) 0.592(4) 0.043(8) Uiso 1 1 d . . . H8 H 0.0536(11) 0.111(3) 0.472(4) 0.036(7) Uiso 1 1 d . . . O4 O 0.17026(7) 1.04096(16) 0.3083(2) 0.0293(3) Uani 1 1 d . . . H10 H 0.1697(12) 1.114(3) 0.340(4) 0.046(8) Uiso 1 1 d . . . O5 O 0.15417(6) 0.99550(15) -0.27095(18) 0.0235(3) Uani 1 1 d . . . H11 H 0.1863(13) 1.006(3) -0.311(4) 0.046(8) Uiso 1 1 d . . . H12 H 0.1437(13) 0.928(3) -0.320(5) 0.056(9) Uiso 1 1 d . . . O6 O 0.08380(6) 1.10697(15) 0.0273(3) 0.0313(3) Uani 1 1 d . . . H13 H 0.0759(14) 1.169(4) 0.072(5) 0.063(11) Uiso 1 1 d . . . H14 H 0.0589(12) 1.071(3) -0.025(4) 0.045(8) Uiso 1 1 d . . . O7 O 0.0000 0.0000 0.8174(3) 0.0297(4) Uani 1 2 d S . . H15 H -0.0126(12) 0.049(3) 0.751(4) 0.036(8) Uiso 1 1 d . . . H16 H 0.0139(11) -0.048(3) 0.272(4) 0.029(7) Uiso 1 1 d . . . O8 O 0.0000 0.0000 0.3269(3) 0.0331(5) Uani 1 2 d S . . C1 C 0.13369(7) 0.69428(15) 0.0320(3) 0.0197(3) Uani 1 1 d . . . C2 C 0.23280(7) 0.73142(15) 0.0170(3) 0.0185(3) Uani 1 1 d . . . C3 C -0.18775(7) 0.50784(17) 0.4852(2) 0.0205(3) Uani 1 1 d . . . C4 C -0.11671(7) 0.34509(16) 0.5461(3) 0.0187(3) Uani 1 1 d . . . H1 H 0.1901(10) 0.577(3) -0.026(4) 0.037(7) Uiso 1 1 d . . . H2 H -0.1904(10) 0.340(2) 0.529(3) 0.022(6) Uiso 1 1 d . . . H9 H 0.1952(13) 1.009(4) 0.349(4) 0.049(9) Uiso 1 1 d . . . H6 H 0.1111(19) 0.352(5) 0.862(7) 0.110(16) 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 0.01470(12) 0.01164(11) 0.02365(13) -0.00062(11) -0.00006(10) 0.00027(9) Mn3 0.01488(12) 0.01734(12) 0.02631(14) -0.00064(11) -0.00053(11) -0.00113(9) N1 0.0151(6) 0.0137(6) 0.0330(9) -0.0008(6) 0.0048(6) 0.0007(5) N2 0.0181(7) 0.0196(7) 0.0404(9) -0.0005(7) 0.0074(7) -0.0009(6) N3 0.0202(7) 0.0214(7) 0.0461(11) 0.0008(8) 0.0077(7) -0.0025(6) N4 0.0186(7) 0.0169(7) 0.0479(11) 0.0003(7) 0.0032(8) -0.0019(5) N5 0.0162(7) 0.0123(6) 0.0572(12) -0.0096(8) 0.0030(8) 0.0009(5) N6 0.0159(6) 0.0125(6) 0.0379(9) -0.0005(7) -0.0008(7) 0.0015(5) N7 0.0176(7) 0.0133(7) 0.0629(12) -0.0025(8) -0.0043(8) -0.0002(5) N8 0.0157(7) 0.0146(7) 0.0608(13) -0.0023(8) -0.0041(8) 0.0003(5) N9 0.0153(6) 0.0120(6) 0.0409(9) -0.0010(7) -0.0008(7) -0.0001(5) N10 0.0156(6) 0.0175(6) 0.0376(8) 0.0056(7) -0.0008(7) 0.0008(5) N11 0.0172(7) 0.0200(7) 0.0527(12) 0.0085(8) -0.0008(8) 0.0032(6) N12 0.0153(7) 0.0232(8) 0.0554(12) 0.0095(8) -0.0023(8) 0.0024(6) N13 0.0140(6) 0.0225(7) 0.0504(10) 0.0077(8) -0.0020(7) 0.0000(5) N14 0.0104(6) 0.0179(7) 0.0586(12) 0.0093(8) -0.0024(8) -0.0033(6) N15 0.0159(7) 0.0170(7) 0.0382(9) 0.0063(7) -0.0002(7) -0.0001(6) N16 0.0170(7) 0.0200(7) 0.0367(9) 0.0072(7) -0.0005(7) 0.0011(6) N17 0.0147(6) 0.0179(7) 0.0322(9) 0.0026(6) -0.0007(6) 0.0021(5) N18 0.0126(6) 0.0158(6) 0.0306(8) 0.0039(6) 0.0002(6) 0.0007(5) O1 0.0228(7) 0.0368(8) 0.0289(7) 0.0024(6) -0.0050(6) -0.0083(6) O2 0.0366(8) 0.0349(9) 0.0287(8) 0.0006(7) -0.0063(6) 0.0050(7) O3 0.0260(7) 0.0190(6) 0.0531(9) 0.0010(7) -0.0039(8) 0.0020(5) O4 0.0361(9) 0.0248(8) 0.0270(7) -0.0041(6) -0.0061(7) 0.0066(7) O5 0.0230(7) 0.0219(7) 0.0255(6) -0.0048(6) 0.0026(5) -0.0066(6) O6 0.0212(7) 0.0245(7) 0.0481(9) -0.0051(7) -0.0019(7) 0.0061(5) O7 0.0303(11) 0.0266(11) 0.0323(11) 0.000 0.000 0.0058(9) O8 0.0353(12) 0.0288(11) 0.0351(12) 0.000 0.000 0.0083(10) C1 0.0170(7) 0.0127(7) 0.0294(8) -0.0012(7) -0.0006(8) -0.0007(6) C2 0.0162(7) 0.0139(7) 0.0254(9) -0.0003(7) 0.0004(7) 0.0010(6) C3 0.0136(7) 0.0203(7) 0.0277(9) 0.0048(8) 0.0001(7) -0.0001(6) C4 0.0145(7) 0.0159(7) 0.0257(8) 0.0025(7) 0.0003(7) 0.0011(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O4 2.1387(16) . ? Mn1 O6 2.1767(14) . ? Mn1 O5 2.2172(14) . ? Mn1 N9 2.2251(14) . ? Mn1 N1 2.2304(14) . ? Mn1 N6 2.2743(14) 4 ? Mn2 O3 2.1637(14) . ? Mn2 O2 2.1881(16) . ? Mn2 O1 2.1957(15) . ? Mn2 N10 2.2202(14) 2_565 ? Mn2 N18 2.2508(14) 2_565 ? Mn2 N17 2.2634(15) . ? N1 C1 1.332(2) . ? N1 N2 1.355(2) . ? N2 N3 1.292(2) . ? N3 N4 1.354(2) . ? N4 C1 1.331(2) . ? N5 C2 1.362(2) . ? N5 C1 1.370(2) . ? N5 H1 0.82(3) . ? N6 C2 1.336(2) . ? N6 N7 1.354(2) . ? N6 Mn1 2.2743(14) 4_545 ? N7 N8 1.294(2) . ? N8 N9 1.351(2) . ? N9 C2 1.330(2) . ? N10 C3 1.326(2) . ? N10 N11 1.356(2) . ? N10 Mn2 2.2202(14) 2_565 ? N11 N12 1.289(2) . ? N12 N13 1.354(2) . ? N13 C3 1.332(2) . ? N14 C3 1.369(2) . ? N14 C4 1.370(2) . ? N14 H2 0.65(2) . ? N15 C4 1.341(2) . ? N15 N16 1.342(2) . ? N16 N17 1.300(2) . ? N17 N18 1.3572(19) . ? N18 C4 1.329(2) . ? N18 Mn2 2.2508(14) 2_565 ? O1 H3 0.85(3) . ? O1 H4 0.94(5) . ? O2 H5 0.96(5) . ? O2 H6 0.90(5) . ? O3 H7 0.85(3) . ? O3 H8 0.77(3) . ? O4 H10 0.79(3) . ? O4 H9 0.75(3) . ? O5 H11 0.83(3) . ? O5 H12 0.82(4) . ? O6 H13 0.75(4) . ? O6 H14 0.80(3) . ? O7 H15 0.77(3) . ? O8 H16 0.72(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 O4 Mn1 O6 88.82(7) . . ? O4 Mn1 O5 171.52(6) . . ? O6 Mn1 O5 86.53(6) . . ? O4 Mn1 N9 91.69(7) . . ? O6 Mn1 N9 167.89(6) . . ? O5 Mn1 N9 94.35(6) . . ? O4 Mn1 N1 93.99(6) . . ? O6 Mn1 N1 89.79(5) . . ? O5 Mn1 N1 93.07(6) . . ? N9 Mn1 N1 78.11(5) . . ? O4 Mn1 N6 88.32(7) . 4 ? O6 Mn1 N6 94.96(6) . 4 ? O5 Mn1 N6 85.04(6) . 4 ? N9 Mn1 N6 97.14(5) . 4 ? N1 Mn1 N6 174.76(5) . 4 ? O3 Mn2 O2 90.35(7) . . ? O3 Mn2 O1 91.02(7) . . ? O2 Mn2 O1 176.61(7) . . ? O3 Mn2 N10 91.32(5) . 2_565 ? O2 Mn2 N10 90.71(7) . 2_565 ? O1 Mn2 N10 86.16(6) . 2_565 ? O3 Mn2 N18 169.54(5) . 2_565 ? O2 Mn2 N18 86.49(7) . 2_565 ? O1 Mn2 N18 91.62(6) . 2_565 ? N10 Mn2 N18 78.77(5) 2_565 2_565 ? O3 Mn2 N17 88.07(5) . . ? O2 Mn2 N17 91.01(6) . . ? O1 Mn2 N17 92.13(6) . . ? N10 Mn2 N17 178.18(7) 2_565 . ? N18 Mn2 N17 101.94(5) 2_565 . ? C1 N1 N2 104.53(14) . . ? C1 N1 Mn1 129.88(12) . . ? N2 N1 Mn1 124.90(11) . . ? N3 N2 N1 108.87(15) . . ? N2 N3 N4 110.82(15) . . ? C1 N4 N3 103.46(14) . . ? C2 N5 C1 123.91(14) . . ? C2 N5 H1 120.3(17) . . ? C1 N5 H1 113.7(17) . . ? C2 N6 N7 104.30(13) . . ? C2 N6 Mn1 144.08(12) . 4_545 ? N7 N6 Mn1 110.76(10) . 4_545 ? N8 N7 N6 109.62(14) . . ? N7 N8 N9 109.81(14) . . ? C2 N9 N8 104.52(13) . . ? C2 N9 Mn1 131.20(11) . . ? N8 N9 Mn1 124.28(11) . . ? C3 N10 N11 104.44(13) . . ? C3 N10 Mn2 132.40(11) . 2_565 ? N11 N10 Mn2 122.63(11) . 2_565 ? N12 N11 N10 109.63(15) . . ? N11 N12 N13 109.75(15) . . ? C3 N13 N12 104.27(14) . . ? C3 N14 C4 125.11(15) . . ? C3 N14 H2 116(2) . . ? C4 N14 H2 119(2) . . ? C4 N15 N16 104.69(14) . . ? N17 N16 N15 109.59(14) . . ? N16 N17 N18 109.83(14) . . ? N16 N17 Mn2 120.62(11) . . ? N18 N17 Mn2 128.57(11) . . ? C4 N18 N17 104.13(13) . . ? C4 N18 Mn2 128.51(11) . 2_565 ? N17 N18 Mn2 124.06(10) . 2_565 ? Mn2 O1 H3 123.4(18) . . ? Mn2 O1 H4 105(3) . . ? H3 O1 H4 103(3) . . ? Mn2 O2 H5 113(3) . . ? Mn2 O2 H6 121(3) . . ? H5 O2 H6 94(4) . . ? Mn2 O3 H7 125.6(19) . . ? Mn2 O3 H8 120(2) . . ? H7 O3 H8 114(3) . . ? Mn1 O4 H10 118(2) . . ? Mn1 O4 H9 113(2) . . ? H10 O4 H9 108(3) . . ? Mn1 O5 H11 105(2) . . ? Mn1 O5 H12 120(2) . . ? H11 O5 H12 104(3) . . ? Mn1 O6 H13 130(3) . . ? Mn1 O6 H14 115(2) . . ? H13 O6 H14 115(3) . . ? N4 C1 N1 112.30(15) . . ? N4 C1 N5 122.02(15) . . ? N1 C1 N5 125.68(15) . . ? N9 C2 N6 111.73(15) . . ? N9 C2 N5 125.06(15) . . ? N6 C2 N5 123.20(14) . . ? N10 C3 N13 111.90(15) . . ? N10 C3 N14 125.12(15) . . ? N13 C3 N14 122.98(16) . . ? N18 C4 N15 111.75(14) . . ? N18 C4 N14 126.93(15) . . ? N15 C4 N14 121.31(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.238 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.073 data_co5 _database_code_depnum_ccdc_archive 'CCDC 660797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 Co N18 Na2 O2' _chemical_formula_sum 'C4 H6 Co N18 Na2 O2' _chemical_formula_weight 443.18 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/c _symmetry_space_group_name_Hall -p2ybc 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 9.4760(12) _cell_length_b 9.4375(11) _cell_length_c 8.2912(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.035(7) _cell_angle_gamma 90.00 _cell_volume 700.94(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1624 _cell_measurement_theta_min 2.274 _cell_measurement_theta_max 27.539 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.209 _exptl_crystal_size_mid 0.207 _exptl_crystal_size_min 0.043 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.1 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 442 _exptl_absorpt_coefficient_mu 1.344 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5593 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1586 _reflns_number_gt 1436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001-2005) ' _computing_cell_refinement 'SAINT (Bruker, 2001-2005)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001-2005)' _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^)+(0.0317P)^2^+0.3461P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1586 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Co1 Co 0.0000 0.5000 0.0000 0.01200(12) Uani 1 2 d S . . Na1 Na 0.38788(8) 0.30333(8) 0.05602(10) 0.0274(2) Uani 1 1 d . . . N2 N 0.34476(16) 0.55692(16) 0.07674(19) 0.0206(3) Uani 1 1 d . . . N1 N 0.21632(16) 0.59453(15) 0.10541(18) 0.0167(3) Uani 1 1 d . . . N3 N 0.43696(17) 0.66282(18) 0.1135(2) 0.0267(4) Uani 1 1 d . . . N4 N 0.37565(18) 0.77366(17) 0.1714(2) 0.0273(4) Uani 1 1 d . . . C1 C 0.24183(19) 0.72671(18) 0.1646(2) 0.0173(3) Uani 1 1 d . . . N7 N -0.16651(16) 0.62648(16) 0.23804(18) 0.0187(3) Uani 1 1 d . . . N9 N -0.05481(16) 0.82528(15) 0.32887(18) 0.0168(3) Uani 1 1 d . . . N8 N -0.17113(16) 0.74028(16) 0.32411(19) 0.0193(3) Uani 1 1 d . . . C2 C 0.01766(18) 0.75648(17) 0.23973(19) 0.0148(3) Uani 1 1 d . . . N6 N -0.04734(16) 0.63348(15) 0.18128(17) 0.0162(3) Uani 1 1 d . . . N5 N 0.14308(18) 0.80875(16) 0.2128(2) 0.0227(3) Uani 1 1 d . . . O2 O 0.3546(3) 0.0631(2) -0.0134(3) 0.0496(5) Uani 1 1 d . . . H1 H 0.169(2) 0.890(3) 0.248(3) 0.030(6) Uiso 1 1 d . . . H3 H 0.365(7) 0.015(5) 0.046(7) 0.12(2) Uiso 1 1 d . . . H2 H 0.313(10) 0.037(8) -0.089(12) 0.26(5) 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 Co1 0.01376(18) 0.00965(17) 0.01417(17) -0.00049(10) 0.00668(12) -0.00046(11) Na1 0.0244(4) 0.0243(4) 0.0352(4) 0.0000(3) 0.0119(3) 0.0036(3) N2 0.0154(7) 0.0216(8) 0.0258(8) -0.0021(6) 0.0081(6) 0.0027(6) N1 0.0156(7) 0.0150(7) 0.0210(7) -0.0024(5) 0.0081(6) 0.0008(6) N3 0.0184(8) 0.0286(9) 0.0361(9) -0.0096(7) 0.0130(7) -0.0035(7) N4 0.0218(8) 0.0267(9) 0.0387(9) -0.0131(7) 0.0173(7) -0.0087(7) C1 0.0184(9) 0.0172(8) 0.0180(8) -0.0027(6) 0.0081(7) -0.0025(7) N7 0.0192(8) 0.0177(7) 0.0224(7) -0.0042(5) 0.0111(6) -0.0029(6) N9 0.0160(7) 0.0162(7) 0.0203(7) -0.0044(5) 0.0090(6) -0.0019(6) N8 0.0183(8) 0.0175(7) 0.0241(7) -0.0048(6) 0.0098(6) -0.0023(6) C2 0.0160(8) 0.0136(8) 0.0160(7) -0.0013(6) 0.0066(6) 0.0003(6) N6 0.0174(7) 0.0147(7) 0.0189(7) -0.0024(5) 0.0093(5) -0.0023(6) N5 0.0238(8) 0.0147(7) 0.0367(9) -0.0112(6) 0.0198(7) -0.0071(6) O2 0.0696(13) 0.0297(9) 0.0516(12) 0.0015(8) 0.0227(10) 0.0034(9) _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 Co1 N6 2.1183(14) . ? Co1 N6 2.1183(14) 3_565 ? Co1 N9 2.1263(14) 4_575 ? Co1 N9 2.1263(14) 2_545 ? Co1 N1 2.1432(14) . ? Co1 N1 2.1432(14) 3_565 ? Na1 O2 2.335(2) . ? Na1 N2 2.4433(17) . ? Na1 N3 2.5208(18) 3_665 ? Na1 N8 2.6253(17) 2_545 ? Na1 N4 2.6274(19) 2_645 ? Na1 N7 2.7290(17) 3_565 ? Na1 N3 3.0092(18) 2_645 ? N2 N3 1.297(2) . ? N2 N1 1.361(2) . ? N1 C1 1.333(2) . ? N3 N4 1.358(2) . ? N3 Na1 2.5208(18) 3_665 ? N3 Na1 3.0092(18) 2_655 ? N4 C1 1.327(2) . ? N4 Na1 2.6274(19) 2_655 ? C1 N5 1.371(2) . ? N7 N8 1.298(2) . ? N7 N6 1.359(2) . ? N7 Na1 2.7290(17) 3_565 ? N9 C2 1.331(2) . ? N9 N8 1.353(2) . ? N9 Co1 2.1263(14) 2 ? N8 Na1 2.6253(17) 2 ? C2 N6 1.329(2) . ? C2 N5 1.371(2) . ? N5 H1 0.83(2) . ? O2 H3 0.65(5) . ? O2 H2 0.67(10) . ? 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 Co1 N6 180.00(5) . 3_565 ? N6 Co1 N9 87.14(5) . 4_575 ? N6 Co1 N9 92.86(5) 3_565 4_575 ? N6 Co1 N9 92.86(5) . 2_545 ? N6 Co1 N9 87.14(5) 3_565 2_545 ? N9 Co1 N9 180.00(5) 4_575 2_545 ? N6 Co1 N1 81.88(5) . . ? N6 Co1 N1 98.12(5) 3_565 . ? N9 Co1 N1 86.69(5) 4_575 . ? N9 Co1 N1 93.31(5) 2_545 . ? N6 Co1 N1 98.12(5) . 3_565 ? N6 Co1 N1 81.88(5) 3_565 3_565 ? N9 Co1 N1 93.31(5) 4_575 3_565 ? N9 Co1 N1 86.69(5) 2_545 3_565 ? N1 Co1 N1 180.0 . 3_565 ? O2 Na1 N2 162.97(8) . . ? O2 Na1 N3 92.65(7) . 3_665 ? N2 Na1 N3 94.05(6) . 3_665 ? O2 Na1 N8 79.27(7) . 2_545 ? N2 Na1 N8 91.49(5) . 2_545 ? N3 Na1 N8 168.11(6) 3_665 2_545 ? O2 Na1 N4 96.73(8) . 2_645 ? N2 Na1 N4 99.16(6) . 2_645 ? N3 Na1 N4 87.77(6) 3_665 2_645 ? N8 Na1 N4 101.73(5) 2_545 2_645 ? O2 Na1 N7 90.74(8) . 3_565 ? N2 Na1 N7 74.19(5) . 3_565 ? N3 Na1 N7 85.71(5) 3_665 3_565 ? N8 Na1 N7 85.70(5) 2_545 3_565 ? N4 Na1 N7 170.30(6) 2_645 3_565 ? O2 Na1 N3 77.68(8) . 2_645 ? N2 Na1 N3 115.01(6) . 2_645 ? N3 Na1 N3 107.19(6) 3_665 2_645 ? N8 Na1 N3 79.79(5) 2_545 2_645 ? N4 Na1 N3 26.80(5) 2_645 2_645 ? N7 Na1 N3 162.84(5) 3_565 2_645 ? N3 N2 N1 109.28(14) . . ? N3 N2 Na1 131.01(12) . . ? N1 N2 Na1 116.57(11) . . ? C1 N1 N2 104.08(14) . . ? C1 N1 Co1 125.03(11) . . ? N2 N1 Co1 127.66(11) . . ? N2 N3 N4 110.10(14) . . ? N2 N3 Na1 118.84(11) . 3_665 ? N4 N3 Na1 122.34(12) . 3_665 ? N2 N3 Na1 133.07(12) . 2_655 ? N4 N3 Na1 60.73(10) . 2_655 ? Na1 N3 Na1 100.60(6) 3_665 2_655 ? C1 N4 N3 103.94(14) . . ? C1 N4 Na1 127.39(12) . 2_655 ? N3 N4 Na1 92.47(11) . 2_655 ? N4 C1 N1 112.58(15) . . ? N4 C1 N5 122.19(15) . . ? N1 C1 N5 125.22(15) . . ? N8 N7 N6 109.32(13) . . ? N8 N7 Na1 97.84(10) . 3_565 ? N6 N7 Na1 99.33(10) . 3_565 ? C2 N9 N8 104.92(13) . . ? C2 N9 Co1 133.71(11) . 2 ? N8 N9 Co1 119.90(10) . 2 ? N7 N8 N9 109.47(13) . . ? N7 N8 Na1 124.50(11) . 2 ? N9 N8 Na1 125.79(10) . 2 ? N6 C2 N9 111.53(14) . . ? N6 C2 N5 125.33(14) . . ? N9 C2 N5 123.14(15) . . ? C2 N6 N7 104.76(13) . . ? C2 N6 Co1 126.72(11) . . ? N7 N6 Co1 127.51(11) . . ? C2 N5 C1 123.69(15) . . ? C2 N5 H1 117.1(15) . . ? C1 N5 H1 117.9(15) . . ? Na1 O2 H3 121(5) . . ? Na1 O2 H2 126(7) . . ? H3 O2 H2 110(7) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.311 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.062 data_cu1 _database_code_depnum_ccdc_archive 'CCDC 661222' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H5 Cu N9 O2' _chemical_formula_sum 'C2 H5 Cu N9 O2' _chemical_formula_weight 250.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.39620(10) _cell_length_b 9.2177(2) _cell_length_c 14.2410(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.8310(10) _cell_angle_gamma 90.00 _cell_volume 837.75(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1917 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.287 _exptl_crystal_size_mid 0.195 _exptl_crystal_size_min 0.143 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500.0 _exptl_absorpt_coefficient_mu 2.601 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.550 _exptl_absorpt_correction_T_max 0.689 _exptl_absorpt_process_details SADABS _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 none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 12747 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1917 _reflns_number_gt 1772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.1251P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1917 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Cu1 Cu 0.06656(4) 0.63014(3) 0.749677(17) 0.02099(12) Uani 1 1 d . . . N1 N 0.0718(3) 0.6925(2) 0.61707(13) 0.0249(4) Uani 1 1 d . . . N3 N 0.1594(4) 0.8182(3) 0.49832(16) 0.0417(6) Uani 1 1 d . . . N2 N 0.2190(3) 0.7817(3) 0.58364(15) 0.0353(5) Uani 1 1 d . . . C1 C -0.0733(4) 0.6800(3) 0.54640(16) 0.0245(5) Uani 1 1 d . . . N4 N -0.0264(4) 0.7554(3) 0.47185(15) 0.0374(5) Uani 1 1 d . . . N5 N -0.2524(4) 0.5989(3) 0.54856(16) 0.0345(5) Uani 1 1 d . . . O2 O 0.0423(3) 0.5653(2) 0.88331(14) 0.0412(5) Uani 1 1 d . . . O1 O 0.3742(3) 0.6731(3) 0.77267(16) 0.0481(5) Uani 1 1 d . . . N8 N -0.4281(3) 0.3521(2) 0.70619(15) 0.0279(4) Uani 1 1 d . . . N6 N -0.1796(3) 0.5097(2) 0.70498(13) 0.0228(4) Uani 1 1 d . . . C2 C -0.2924(3) 0.5111(2) 0.62231(15) 0.0231(4) Uani 1 1 d . . . N9 N -0.4485(3) 0.4163(2) 0.62019(14) 0.0275(4) Uani 1 1 d . . . N7 N -0.2702(3) 0.4059(2) 0.75675(14) 0.0268(4) Uani 1 1 d . . . H1 H -0.323(5) 0.602(3) 0.507(2) 0.029(8) Uiso 1 1 d . . . H3 H 0.177(7) 0.600(4) 0.930(3) 0.064(12) Uiso 1 1 d . . . H2 H -0.094(6) 0.609(4) 0.907(3) 0.050(10) Uiso 1 1 d . . . H4 H 0.419(6) 0.722(4) 0.838(3) 0.056(10) Uiso 1 1 d . . . H5 H 0.487(8) 0.597(6) 0.757(3) 0.085(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02101(17) 0.02461(18) 0.01661(17) 0.00082(9) -0.00437(10) -0.00235(10) N1 0.0240(9) 0.0307(10) 0.0194(9) 0.0021(8) -0.0032(7) -0.0077(8) N3 0.0391(12) 0.0551(15) 0.0302(12) 0.0115(11) -0.0033(9) -0.0207(11) N2 0.0320(10) 0.0456(13) 0.0275(10) 0.0063(9) -0.0033(8) -0.0173(10) C1 0.0245(10) 0.0287(11) 0.0197(10) 0.0034(9) -0.0038(8) -0.0049(9) N4 0.0367(11) 0.0499(14) 0.0243(10) 0.0116(10) -0.0069(9) -0.0165(10) N5 0.0318(11) 0.0468(13) 0.0229(10) 0.0122(10) -0.0136(9) -0.0180(10) O2 0.0448(11) 0.0478(12) 0.0301(9) 0.0026(9) -0.0036(8) 0.0037(9) O1 0.0342(10) 0.0715(16) 0.0376(11) -0.0093(11) -0.0050(9) -0.0015(11) N8 0.0315(10) 0.0261(10) 0.0254(10) 0.0017(8) -0.0028(8) -0.0082(8) N6 0.0260(9) 0.0231(9) 0.0187(9) 0.0031(7) -0.0040(7) -0.0054(7) C2 0.0239(10) 0.0243(10) 0.0202(10) 0.0013(8) -0.0047(8) -0.0043(8) N9 0.0286(10) 0.0296(10) 0.0233(9) 0.0027(8) -0.0053(8) -0.0085(8) N7 0.0316(10) 0.0250(10) 0.0229(9) 0.0032(8) -0.0041(8) -0.0076(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 Cu1 N1 1.9765(19) . ? Cu1 N6 1.9960(18) . ? Cu1 O2 2.011(2) . ? Cu1 O1 2.012(2) . ? Cu1 N8 2.332(2) 2_456 ? N1 C1 1.327(3) . ? N1 N2 1.360(3) . ? N3 N2 1.293(3) . ? N3 N4 1.353(3) . ? C1 N4 1.320(3) . ? C1 N5 1.370(3) . ? N5 C2 1.364(3) . ? N5 H1 0.72(3) . ? O2 H3 1.10(4) . ? O2 H2 1.04(4) . ? O1 H4 1.05(4) . ? O1 H5 1.04(5) . ? N8 N7 1.299(3) . ? N8 N9 1.359(3) . ? N8 Cu1 2.332(2) 2_446 ? N6 C2 1.339(3) . ? N6 N7 1.361(3) . ? C2 N9 1.326(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 N1 Cu1 N6 85.43(8) . . ? N1 Cu1 O2 176.53(8) . . ? N6 Cu1 O2 91.57(8) . . ? N1 Cu1 O1 91.12(9) . . ? N6 Cu1 O1 154.61(10) . . ? O2 Cu1 O1 92.34(9) . . ? N1 Cu1 N8 91.91(8) . 2_456 ? N6 Cu1 N8 105.55(8) . 2_456 ? O2 Cu1 N8 87.19(8) . 2_456 ? O1 Cu1 N8 99.69(9) . 2_456 ? C1 N1 N2 104.62(18) . . ? C1 N1 Cu1 130.05(16) . . ? N2 N1 Cu1 124.52(15) . . ? N2 N3 N4 110.4(2) . . ? N3 N2 N1 108.58(19) . . ? N4 C1 N1 112.3(2) . . ? N4 C1 N5 122.7(2) . . ? N1 C1 N5 125.0(2) . . ? C1 N4 N3 104.10(19) . . ? C2 N5 C1 122.8(2) . . ? C2 N5 H1 121(2) . . ? C1 N5 H1 116(2) . . ? Cu1 O2 H3 112(2) . . ? Cu1 O2 H2 108(2) . . ? H3 O2 H2 110(3) . . ? Cu1 O1 H4 116(2) . . ? Cu1 O1 H5 121(3) . . ? H4 O1 H5 109(3) . . ? N7 N8 N9 110.94(19) . . ? N7 N8 Cu1 118.76(15) . 2_446 ? N9 N8 Cu1 127.57(15) . 2_446 ? C2 N6 N7 105.03(17) . . ? C2 N6 Cu1 129.95(15) . . ? N7 N6 Cu1 125.01(14) . . ? N9 C2 N6 112.0(2) . . ? N9 C2 N5 123.6(2) . . ? N6 C2 N5 124.4(2) . . ? C2 N9 N8 103.87(18) . . ? N8 N7 N6 108.16(18) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.597 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.078 # Attachment '1-Co.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 661223' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C6 H6 Co N27), 8(H2 O), O' _chemical_formula_sum 'C12 H28 Co2 N54 O9' _chemical_formula_weight 1190.74 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.3207(3) _cell_length_b 13.0862(4) _cell_length_c 15.3142(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.104(2) _cell_angle_gamma 90.00 _cell_volume 2218.28(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5156 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 27.630 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.287 _exptl_crystal_size_mid 0.195 _exptl_crystal_size_min 0.143 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.859 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.818 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_process_details SADAB _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 none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 33524 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.63 _reflns_number_total 5071 _reflns_number_gt 4345 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+2.2570P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5156 _refine_ls_number_parameters 393 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.040 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 Co1 Co 0.81885(3) 0.82690(2) 0.220920(19) 0.02271(12) Uani 1 1 d . . . N19 N 0.92687(18) 0.75592(14) 0.16132(13) 0.0266(4) Uani 1 1 d . . . N1 N 0.95501(17) 0.86355(15) 0.31264(13) 0.0262(4) Uani 1 1 d . . . N6 N 0.71851(18) 0.89905(16) 0.28689(13) 0.0269(4) Uani 1 1 d . . . N5 N 0.85938(19) 0.93402(18) 0.42403(14) 0.0311(5) Uani 1 1 d . . . N24 N 0.84368(18) 0.94776(15) 0.15774(13) 0.0252(4) Uani 1 1 d . . . N15 N 0.68767(19) 0.78777(16) 0.12542(14) 0.0295(4) Uani 1 1 d . . . N10 N 0.78936(19) 0.70361(16) 0.28111(14) 0.0303(4) Uani 1 1 d . . . N25 N 0.7816(2) 1.03622(16) 0.15796(15) 0.0344(5) Uani 1 1 d . . . N7 N 0.5986(2) 0.91798(19) 0.25773(15) 0.0374(5) Uani 1 1 d . . . N27 N 0.8982(2) 1.05303(17) 0.06270(15) 0.0358(5) Uani 1 1 d . . . N26 N 0.8148(2) 1.09774(17) 0.10170(16) 0.0376(5) Uani 1 1 d . . . N20 N 0.9654(2) 0.65761(17) 0.18098(18) 0.0426(6) Uani 1 1 d . . . N23 N 0.9925(2) 0.89056(16) 0.07793(15) 0.0352(5) Uani 1 1 d . . . H5 H 1.0404 0.9076 0.0436 0.042 Uiso 1 1 calc R . . N22 N 1.0732(2) 0.72324(17) 0.09755(16) 0.0369(5) Uani 1 1 d . . . H6 H 1.1274 0.7295 0.0660 0.044 Uiso 1 1 calc R . . N11 N 0.8409(3) 0.6810(2) 0.36784(17) 0.0456(6) Uani 1 1 d . . . N4 N 1.07138(19) 0.92754(18) 0.43253(14) 0.0339(5) Uani 1 1 d . . . N2 N 1.07191(19) 0.85442(18) 0.30464(15) 0.0345(5) Uani 1 1 d . . . N9 N 0.6513(2) 0.97855(18) 0.38898(15) 0.0360(5) Uani 1 1 d . . . H2 H 0.6476 1.0085 0.4383 0.043 Uiso 1 1 calc R . . N3 N 1.1392(2) 0.89237(19) 0.37639(15) 0.0374(5) Uani 1 1 d . . . N18 N 0.5682(2) 0.6927(2) 0.02672(19) 0.0496(7) Uani 1 1 d . . . N8 N 0.5585(2) 0.9660(2) 0.31880(17) 0.0430(6) Uani 1 1 d . . . N17 N 0.5728(3) 0.7882(2) -0.00566(18) 0.0520(7) Uani 1 1 d . . . N21 N 1.0524(3) 0.63843(18) 0.14244(19) 0.0487(6) Uani 1 1 d . . . N12 N 0.8115(3) 0.5892(2) 0.3844(2) 0.0581(8) Uani 1 1 d . . . N13 N 0.7410(3) 0.5511(2) 0.3089(2) 0.0594(8) Uani 1 1 d . . . H4 H 0.7106 0.4906 0.3027 0.071 Uiso 1 1 calc R . . N14 N 0.6622(3) 0.6138(2) 0.1622(2) 0.0546(8) Uani 1 1 d . . . N16 N 0.6436(2) 0.8454(2) 0.05174(17) 0.0447(6) Uani 1 1 d . . . C2 C 0.7494(2) 0.93700(18) 0.36928(15) 0.0270(5) Uani 1 1 d . . . C3 C 0.6394(2) 0.6959(2) 0.1066(2) 0.0375(6) Uani 1 1 d . . . C1 C 0.9586(2) 0.90885(18) 0.39091(15) 0.0269(5) Uani 1 1 d . . . C4 C 0.7265(3) 0.6221(2) 0.2465(2) 0.0409(6) Uani 1 1 d . . . C6 C 0.9137(2) 0.96108(18) 0.09891(16) 0.0279(5) Uani 1 1 d . . . C5 C 0.9961(2) 0.79495(19) 0.11031(15) 0.0276(5) Uani 1 1 d . . . O1 O 0.61883(19) 0.05862(15) 0.54291(13) 0.0320(4) Uani 1 1 d . . . O2 O 0.2667(2) 0.75043(19) 0.0290(2) 0.0493(6) Uani 1 1 d . . . O3 O 0.4247(6) 0.8144(4) 0.8117(3) 0.1340(18) Uani 1 1 d D . . O4 O 0.6804(8) 0.3537(5) 0.2916(7) 0.292(6) Uani 1 1 d D . . O5 O 0.5921(5) 0.4525(5) 0.4261(4) 0.0828(18) Uani 0.50 1 d P . . H1 H 0.870(3) 0.971(3) 0.465(2) 0.052(10) Uiso 1 1 d . . . H3 H 0.633(4) 0.568(4) 0.150(3) 0.072(14) Uiso 1 1 d . . . H7 H 0.302(4) 0.787(4) 0.063(3) 0.069(15) Uiso 1 1 d . . . H8 H 0.246(4) 0.779(4) -0.013(3) 0.070(16) Uiso 1 1 d . . . H10 H 0.459(4) 0.869(2) 0.840(3) 0.069(14) Uiso 1 1 d D . . H9 H 0.352(5) 0.828(18) 0.81(3) 1.0(3) Uiso 1 1 d D . . H12 H 0.678(3) 0.303(2) 0.258(2) 0.042(10) Uiso 1 1 d D . . H13 H 0.676(4) 0.091(3) 0.560(2) 0.050(11) Uiso 1 1 d . . . H14 H 0.564(3) 0.098(3) 0.523(2) 0.052(10) Uiso 1 1 d . . . H11 H 0.622(2) 0.346(2) 0.3174(19) 0.021(7) 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 Co1 0.02392(18) 0.02216(18) 0.02254(18) -0.00334(11) 0.00599(12) -0.00368(11) N19 0.0309(10) 0.0204(9) 0.0291(10) -0.0034(7) 0.0081(8) -0.0014(8) N1 0.0254(10) 0.0282(10) 0.0254(9) -0.0047(8) 0.0062(8) -0.0023(8) N6 0.0246(9) 0.0308(10) 0.0261(10) -0.0027(8) 0.0073(8) -0.0027(8) N5 0.0309(11) 0.0375(12) 0.0257(10) -0.0091(9) 0.0075(9) -0.0023(9) N24 0.0275(10) 0.0232(9) 0.0258(9) -0.0040(7) 0.0077(8) -0.0015(7) N15 0.0307(10) 0.0269(10) 0.0299(10) -0.0028(8) 0.0038(8) -0.0037(8) N10 0.0312(11) 0.0297(10) 0.0309(10) 0.0033(8) 0.0085(9) -0.0027(8) N25 0.0419(12) 0.0250(10) 0.0396(12) -0.0022(9) 0.0164(10) 0.0024(9) N7 0.0275(11) 0.0495(14) 0.0360(12) -0.0045(10) 0.0085(9) 0.0020(10) N27 0.0438(13) 0.0277(11) 0.0408(12) 0.0041(9) 0.0200(10) 0.0052(9) N26 0.0453(13) 0.0277(11) 0.0455(13) 0.0023(9) 0.0226(11) 0.0056(9) N20 0.0550(15) 0.0226(11) 0.0566(15) 0.0009(10) 0.0260(12) 0.0038(10) N23 0.0410(12) 0.0307(11) 0.0402(12) 0.0072(9) 0.0234(10) 0.0068(9) N22 0.0416(12) 0.0292(11) 0.0451(13) -0.0022(9) 0.0208(10) 0.0046(9) N11 0.0557(16) 0.0454(14) 0.0348(12) 0.0115(10) 0.0072(11) -0.0021(11) N4 0.0295(11) 0.0410(12) 0.0295(10) -0.0080(9) 0.0021(9) 0.0003(9) N2 0.0265(10) 0.0421(12) 0.0340(11) -0.0075(9) 0.0045(9) -0.0004(9) N9 0.0354(12) 0.0434(13) 0.0313(11) -0.0058(9) 0.0120(9) 0.0026(10) N3 0.0275(11) 0.0482(14) 0.0347(11) -0.0104(10) 0.0029(9) 0.0000(9) N18 0.0475(15) 0.0393(13) 0.0515(15) -0.0064(11) -0.0133(12) -0.0071(11) N8 0.0325(12) 0.0559(15) 0.0423(13) -0.0047(11) 0.0119(10) 0.0066(11) N17 0.0548(16) 0.0451(15) 0.0458(14) -0.0010(12) -0.0128(12) -0.0093(12) N21 0.0601(16) 0.0278(12) 0.0669(17) 0.0021(11) 0.0332(14) 0.0073(11) N12 0.0628(18) 0.0541(17) 0.0543(16) 0.0245(14) 0.0051(14) -0.0078(14) N13 0.0504(16) 0.0431(15) 0.077(2) 0.0263(14) -0.0040(15) -0.0148(12) N14 0.0583(17) 0.0301(13) 0.0629(18) 0.0028(12) -0.0157(14) -0.0193(12) N16 0.0464(14) 0.0426(14) 0.0376(13) 0.0034(10) -0.0082(11) -0.0100(11) C2 0.0311(12) 0.0262(11) 0.0265(11) -0.0026(9) 0.0124(10) -0.0029(9) C3 0.0312(13) 0.0313(13) 0.0450(15) -0.0043(11) -0.0032(11) -0.0053(10) C1 0.0293(12) 0.0261(11) 0.0245(11) -0.0031(9) 0.0042(9) -0.0023(9) C4 0.0352(14) 0.0298(13) 0.0550(17) 0.0100(12) 0.0036(13) -0.0067(11) C6 0.0303(12) 0.0266(11) 0.0284(11) 0.0007(9) 0.0099(10) -0.0009(9) C5 0.0295(12) 0.0274(11) 0.0260(11) -0.0046(9) 0.0063(9) 0.0002(9) O1 0.0266(10) 0.0322(10) 0.0368(10) 0.0006(8) 0.0057(8) 0.0029(8) O2 0.0447(13) 0.0416(13) 0.0645(17) 0.0017(13) 0.0178(12) 0.0052(10) O3 0.188(5) 0.125(4) 0.081(3) -0.008(3) 0.010(3) 0.060(4) O4 0.281(9) 0.091(4) 0.367(11) 0.109(5) -0.243(8) -0.095(5) O5 0.069(4) 0.088(4) 0.086(4) 0.017(3) 0.004(3) -0.026(3) _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 Co1 N24 1.906(2) . ? Co1 N19 1.9128(19) . ? Co1 N1 1.916(2) . ? Co1 N6 1.919(2) . ? Co1 N10 1.922(2) . ? Co1 N15 1.922(2) . ? N19 C5 1.320(3) . ? N19 N20 1.372(3) . ? N1 C1 1.330(3) . ? N1 N2 1.360(3) . ? N6 C2 1.333(3) . ? N6 N7 1.360(3) . ? N5 C2 1.348(3) . ? N5 C1 1.367(3) . ? N5 H1 0.78(4) . ? N24 C6 1.331(3) . ? N24 N25 1.354(3) . ? N15 C3 1.326(3) . ? N15 N16 1.362(3) . ? N10 C4 1.329(3) . ? N10 N11 1.366(3) . ? N25 N26 1.291(3) . ? N7 N8 1.285(3) . ? N27 C6 1.321(3) . ? N27 N26 1.351(3) . ? N20 N21 1.274(3) . ? N23 C5 1.343(3) . ? N23 C6 1.368(3) . ? N23 H5 0.8600 . ? N22 C5 1.324(3) . ? N22 N21 1.352(3) . ? N22 H6 0.8600 . ? N11 N12 1.286(4) . ? N4 C1 1.324(3) . ? N4 N3 1.348(3) . ? N2 N3 1.298(3) . ? N9 C2 1.327(3) . ? N9 N8 1.346(3) . ? N9 H2 0.8600 . ? N18 C3 1.317(4) . ? N18 N17 1.349(4) . ? N17 N16 1.296(3) . ? N12 N13 1.355(4) . ? N13 C4 1.318(4) . ? N13 H4 0.8600 . ? N14 C4 1.346(4) . ? N14 C3 1.363(4) . ? N14 H3 0.69(5) . ? O1 H13 0.77(4) . ? O1 H14 0.81(4) . ? O2 H7 0.76(5) . ? O2 H8 0.74(5) . ? O3 H10 0.881(10) . ? O3 H9 0.849(11) . ? O4 H12 0.840(10) . ? O4 H11 0.846(10) . ? 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 N24 Co1 N19 89.06(8) . . ? N24 Co1 N1 89.01(8) . . ? N19 Co1 N1 88.56(8) . . ? N24 Co1 N6 91.46(8) . . ? N19 Co1 N6 176.50(8) . . ? N1 Co1 N6 87.99(8) . . ? N24 Co1 N10 177.96(9) . . ? N19 Co1 N10 90.80(9) . . ? N1 Co1 N10 93.01(9) . . ? N6 Co1 N10 88.80(9) . . ? N24 Co1 N15 90.43(9) . . ? N19 Co1 N15 88.67(9) . . ? N1 Co1 N15 177.18(8) . . ? N6 Co1 N15 94.79(9) . . ? N10 Co1 N15 87.54(9) . . ? C5 N19 N20 107.0(2) . . ? C5 N19 Co1 127.80(17) . . ? N20 N19 Co1 123.82(16) . . ? C1 N1 N2 105.88(19) . . ? C1 N1 Co1 129.81(17) . . ? N2 N1 Co1 124.10(15) . . ? C2 N6 N7 106.8(2) . . ? C2 N6 Co1 127.95(17) . . ? N7 N6 Co1 125.24(16) . . ? C2 N5 C1 120.0(2) . . ? C2 N5 H1 117(3) . . ? C1 N5 H1 116(3) . . ? C6 N24 N25 105.83(19) . . ? C6 N24 Co1 128.67(16) . . ? N25 N24 Co1 125.20(15) . . ? C3 N15 N16 105.0(2) . . ? C3 N15 Co1 128.61(19) . . ? N16 N15 Co1 124.96(17) . . ? C4 N10 N11 107.3(2) . . ? C4 N10 Co1 127.91(19) . . ? N11 N10 Co1 124.49(18) . . ? N26 N25 N24 107.92(19) . . ? N8 N7 N6 109.3(2) . . ? C6 N27 N26 104.6(2) . . ? N25 N26 N27 110.7(2) . . ? N21 N20 N19 108.9(2) . . ? C5 N23 C6 120.8(2) . . ? C5 N23 H5 119.6 . . ? C6 N23 H5 119.6 . . ? C5 N22 N21 108.4(2) . . ? C5 N22 H6 125.8 . . ? N21 N22 H6 125.8 . . ? N12 N11 N10 108.6(2) . . ? C1 N4 N3 104.51(19) . . ? N3 N2 N1 107.5(2) . . ? C2 N9 N8 108.6(2) . . ? C2 N9 H2 125.7 . . ? N8 N9 H2 125.7 . . ? N2 N3 N4 111.0(2) . . ? C3 N18 N17 104.4(2) . . ? N7 N8 N9 107.8(2) . . ? N16 N17 N18 110.6(2) . . ? N20 N21 N22 107.9(2) . . ? N11 N12 N13 107.8(2) . . ? C4 N13 N12 108.7(3) . . ? C4 N13 H4 125.6 . . ? N12 N13 H4 125.6 . . ? C4 N14 C3 121.9(3) . . ? C4 N14 H3 118(4) . . ? C3 N14 H3 119(4) . . ? N17 N16 N15 108.0(2) . . ? N9 C2 N6 107.6(2) . . ? N9 C2 N5 125.3(2) . . ? N6 C2 N5 127.1(2) . . ? N18 C3 N15 112.0(3) . . ? N18 C3 N14 123.6(3) . . ? N15 C3 N14 124.3(3) . . ? N4 C1 N1 111.1(2) . . ? N4 C1 N5 124.1(2) . . ? N1 C1 N5 124.7(2) . . ? N13 C4 N10 107.5(3) . . ? N13 C4 N14 126.7(3) . . ? N10 C4 N14 125.7(3) . . ? N27 C6 N24 111.0(2) . . ? N27 C6 N23 123.5(2) . . ? N24 C6 N23 125.5(2) . . ? N19 C5 N22 107.8(2) . . ? N19 C5 N23 127.1(2) . . ? N22 C5 N23 125.1(2) . . ? H13 O1 H14 107(4) . . ? H7 O2 H8 107(5) . . ? H10 O3 H9 98(2) . . ? H12 O4 H11 106(2) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.329 _refine_diff_density_min -1.033 _refine_diff_density_rms 0.073 data_3 _database_code_depnum_ccdc_archive 'CCDC 684778' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H3 Mn N9 O' _chemical_formula_sum 'C2 H3 Mn N9 O' _chemical_formula_weight 224.07 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4026(7) _cell_length_b 9.7202(9) _cell_length_c 10.5861(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.079(5) _cell_angle_gamma 90.00 _cell_volume 656.23(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1521 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.560 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.239 _exptl_crystal_size_mid 0.193 _exptl_crystal_size_min 0.120 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 1.983 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.638 _exptl_absorpt_correction_T_max 0.788 _exptl_absorpt_process_details SADABS _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 none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5196 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1521 _reflns_number_gt 1404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+1.0469P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0086(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1521 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 1.53216(5) 0.16384(3) 0.36689(3) 0.01310(14) Uani 1 1 d . . . N1 N 1.3660(3) 0.16380(18) 0.54761(17) 0.0152(4) Uani 1 1 d . . . N2 N 1.3519(3) 0.05948(19) 0.63151(17) 0.0167(4) Uani 1 1 d . . . N3 N 1.2746(3) 0.10407(19) 0.73322(17) 0.0180(4) Uani 1 1 d . . . N4 N 1.2314(3) 0.23997(19) 0.72012(16) 0.0159(4) Uani 1 1 d . . . N5 N 1.2819(3) 0.4040(2) 0.56194(17) 0.0172(4) Uani 1 1 d . . . H1 H 1.256(5) 0.461(3) 0.611(3) 0.027(8) Uiso 1 1 d . . . N6 N 1.3516(3) 0.36192(19) 0.34574(17) 0.0160(4) Uani 1 1 d . . . N7 N 1.3103(3) 0.4367(2) 0.23823(17) 0.0189(4) Uani 1 1 d . . . N8 N 1.2181(3) 0.5507(2) 0.26601(18) 0.0192(4) Uani 1 1 d . . . N9 N 1.1922(3) 0.55535(19) 0.39162(18) 0.0182(4) Uani 1 1 d . . . O1 O 1.8188(3) 0.1917(2) 0.49344(17) 0.0224(4) Uani 1 1 d . . . H2 H 1.825(6) 0.139(4) 0.558(4) 0.042(10) Uiso 1 1 d . . . H3 H 1.832(6) 0.267(5) 0.526(4) 0.052(11) Uiso 1 1 d . . . C1 C 1.2927(3) 0.2726(2) 0.60652(19) 0.0132(4) Uani 1 1 d . . . C2 C 1.2744(3) 0.4376(2) 0.4358(2) 0.0138(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 0.0171(2) 0.01070(19) 0.01195(19) -0.00042(11) 0.00365(12) 0.00046(12) N1 0.0194(9) 0.0121(9) 0.0145(8) 0.0007(7) 0.0041(7) 0.0018(7) N2 0.0207(9) 0.0136(9) 0.0163(8) 0.0009(7) 0.0052(7) 0.0017(7) N3 0.0236(10) 0.0136(9) 0.0175(9) 0.0028(7) 0.0064(7) 0.0027(7) N4 0.0212(9) 0.0121(9) 0.0152(8) 0.0011(7) 0.0053(7) 0.0019(7) N5 0.0296(10) 0.0107(9) 0.0124(8) -0.0009(7) 0.0086(7) 0.0030(8) N6 0.0204(9) 0.0146(9) 0.0134(8) 0.0014(7) 0.0036(7) 0.0024(7) N7 0.0248(10) 0.0172(9) 0.0144(8) 0.0019(7) 0.0003(7) 0.0032(8) N8 0.0241(10) 0.0160(9) 0.0170(9) 0.0009(7) -0.0005(7) 0.0034(8) N9 0.0221(9) 0.0149(9) 0.0177(9) -0.0002(7) 0.0018(7) 0.0033(7) O1 0.0274(9) 0.0197(9) 0.0193(8) -0.0014(7) -0.0020(7) -0.0022(7) C1 0.0135(9) 0.0131(10) 0.0131(9) -0.0004(8) 0.0021(7) 0.0010(8) C2 0.0142(9) 0.0117(10) 0.0157(9) 0.0005(7) 0.0021(7) -0.0009(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 Mn1 O1 2.1908(18) . ? Mn1 N6 2.2467(19) . ? Mn1 N1 2.2699(18) . ? Mn1 N2 2.2936(19) 3_856 ? Mn1 N4 2.2949(18) 4_665 ? Mn1 N8 2.3147(19) 2_745 ? N1 C1 1.334(3) . ? N1 N2 1.356(3) . ? N2 N3 1.299(3) . ? N2 Mn1 2.2936(19) 3_856 ? N3 N4 1.354(3) . ? N4 C1 1.336(3) . ? N4 Mn1 2.2949(18) 4_566 ? N5 C1 1.361(3) . ? N5 C2 1.372(3) . ? N6 C2 1.333(3) . ? N6 N7 1.357(3) . ? N7 N8 1.301(3) . ? N8 N9 1.355(3) . ? N8 Mn1 2.3147(19) 2_755 ? N9 C2 1.327(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 O1 Mn1 N6 110.54(7) . . ? O1 Mn1 N1 85.09(7) . . ? N6 Mn1 N1 78.97(6) . . ? O1 Mn1 N2 81.91(7) . 3_856 ? N6 Mn1 N2 167.18(7) . 3_856 ? N1 Mn1 N2 99.74(6) . 3_856 ? O1 Mn1 N4 82.99(7) . 4_665 ? N6 Mn1 N4 83.99(7) . 4_665 ? N1 Mn1 N4 154.26(7) . 4_665 ? N2 Mn1 N4 101.05(7) 3_856 4_665 ? O1 Mn1 N8 158.06(7) . 2_745 ? N6 Mn1 N8 91.39(7) . 2_745 ? N1 Mn1 N8 99.28(7) . 2_745 ? N2 Mn1 N8 76.17(7) 3_856 2_745 ? N4 Mn1 N8 100.28(7) 4_665 2_745 ? C1 N1 N2 103.90(17) . . ? C1 N1 Mn1 127.19(14) . . ? N2 N1 Mn1 127.97(13) . . ? N3 N2 N1 110.22(17) . . ? N3 N2 Mn1 117.17(14) . 3_856 ? N1 N2 Mn1 132.24(13) . 3_856 ? N2 N3 N4 109.28(17) . . ? C1 N4 N3 104.49(17) . . ? C1 N4 Mn1 137.55(15) . 4_566 ? N3 N4 Mn1 116.68(13) . 4_566 ? C1 N5 C2 123.90(19) . . ? C2 N6 N7 104.28(17) . . ? C2 N6 Mn1 128.45(14) . . ? N7 N6 Mn1 127.11(14) . . ? N8 N7 N6 108.99(17) . . ? N7 N8 N9 110.34(17) . . ? N7 N8 Mn1 124.79(14) . 2_755 ? N9 N8 Mn1 116.25(14) . 2_755 ? C2 N9 N8 103.75(18) . . ? N1 C1 N4 112.08(19) . . ? N1 C1 N5 126.22(19) . . ? N4 C1 N5 121.68(19) . . ? N9 C2 N6 112.62(19) . . ? N9 C2 N5 121.8(2) . . ? N6 C2 N5 125.53(19) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.631 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.083 data_2 _database_code_depnum_ccdc_archive 'CCDC 687023' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 Mn N18 Na2 O2' _chemical_formula_sum 'C4 H6 Mn N18 Na2 O2' _chemical_formula_weight 439.19 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.4412(2) _cell_length_b 9.6151(2) _cell_length_c 8.6398(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.874(2) _cell_angle_gamma 90.00 _cell_volume 742.13(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1714 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.510 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.202 _exptl_crystal_size_mid 0.195 _exptl_crystal_size_min 0.063 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.965 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 1.002 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6008 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1614 _reflns_number_gt 1396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001-2005) ' _computing_cell_refinement 'SAINT (Bruker, 2001-2005)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001-2005)' _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^)+(0.0317P)^2^+0.3461P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1686 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.141 _refine_ls_shift/su_mean 0.015 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 0.0000 0.5000 0.0000 0.01558(15) Uani 1 2 d S . . Na1 Na 0.38706(10) 0.30763(10) 0.05534(12) 0.0323(3) Uani 1 1 d . . . N2 N 0.35178(19) 0.5638(2) 0.0810(2) 0.0253(4) Uani 1 1 d . . . N1 N 0.22542(18) 0.59707(18) 0.1165(2) 0.0217(4) Uani 1 1 d . . . N3 N 0.4417(2) 0.6692(2) 0.1144(3) 0.0334(5) Uani 1 1 d . . . N4 N 0.3810(2) 0.7754(2) 0.1753(3) 0.0355(5) Uani 1 1 d . . . C1 C 0.2495(2) 0.7257(2) 0.1741(3) 0.0212(5) Uani 1 1 d . . . N7 N -0.1699(2) 0.6305(2) 0.2340(2) 0.0255(4) Uani 1 1 d . . . N9 N -0.05238(19) 0.82137(19) 0.3291(2) 0.0228(4) Uani 1 1 d . . . N8 N -0.17315(19) 0.7413(2) 0.3189(2) 0.0252(4) Uani 1 1 d . . . C2 C 0.0210(2) 0.7532(2) 0.2452(3) 0.0193(5) Uani 1 1 d . . . N6 N -0.04705(19) 0.63542(19) 0.1840(2) 0.0212(4) Uani 1 1 d . . . N5 N 0.1505(2) 0.8033(2) 0.2253(3) 0.0311(5) Uani 1 1 d . . . O2 O 0.3575(3) 0.0680(3) -0.0034(4) 0.0663(7) Uani 1 1 d . . . H1 H 0.179(3) 0.882(3) 0.261(3) 0.042(8) Uiso 1 1 d . . . H3 H 0.353(6) 0.028(6) 0.063(7) 0.11(2) Uiso 1 1 d . . . H2 H 0.358(16) 0.036(15) -0.06(2) 0.49(11) 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 0.0177(2) 0.0116(2) 0.0193(2) -0.00082(17) 0.00862(17) -0.00116(17) Na1 0.0276(5) 0.0299(6) 0.0415(6) -0.0004(4) 0.0139(4) 0.0050(4) N2 0.0182(9) 0.0257(11) 0.0334(11) -0.0040(8) 0.0104(8) 0.0013(8) N1 0.0175(9) 0.0190(10) 0.0307(10) -0.0039(8) 0.0107(7) -0.0013(7) N3 0.0234(10) 0.0352(12) 0.0460(13) -0.0130(10) 0.0173(9) -0.0061(8) N4 0.0277(11) 0.0335(12) 0.0539(14) -0.0200(10) 0.0250(10) -0.0118(9) C1 0.0185(10) 0.0216(12) 0.0260(11) -0.0053(9) 0.0107(9) -0.0032(8) N7 0.0244(10) 0.0232(10) 0.0335(11) -0.0083(8) 0.0158(8) -0.0042(8) N9 0.0207(9) 0.0203(10) 0.0313(10) -0.0078(8) 0.0140(8) -0.0042(7) N8 0.0230(10) 0.0223(10) 0.0335(11) -0.0087(8) 0.0137(8) -0.0047(8) C2 0.0202(10) 0.0168(11) 0.0225(11) -0.0040(8) 0.0090(8) 0.0005(8) N6 0.0229(9) 0.0188(9) 0.0264(10) -0.0061(8) 0.0141(8) -0.0029(7) N5 0.0306(11) 0.0224(11) 0.0504(13) -0.0176(10) 0.0270(10) -0.0108(9) O2 0.098(2) 0.0371(13) 0.0740(18) 0.0052(13) 0.0416(16) 0.0031(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 Mn1 N1 2.2423(17) . ? Mn1 N1 2.2423(17) 3_565 ? Mn1 N6 2.2083(17) . ? Mn1 N6 2.2083(17) 3_565 ? Mn1 N9 2.2143(17) 4_575 ? Mn1 N9 2.2143(17) 2_545 ? Na1 O2 2.357(3) . ? Na1 N2 2.505(2) . ? Na1 N3 2.519(2) 3_665 ? Na1 N8 2.662(2) 2_545 ? Na1 N4 2.647(2) 2_645 ? Na1 N7 2.737(2) 3_565 ? N2 N3 1.294(3) . ? N2 N1 1.363(2) . ? N1 C1 1.325(3) . ? N3 N4 1.358(3) . ? N3 Na1 2.519(2) 3_665 ? N4 C1 1.327(3) . ? N4 Na1 2.647(2) 2_655 ? C1 N5 1.377(3) . ? N7 N8 1.299(3) . ? N7 N6 1.363(2) . ? N7 Na1 2.737(2) 3_565 ? N9 C2 1.327(3) . ? N9 N8 1.355(2) . ? N9 Mn1 2.2143(17) 2 ? N8 Na1 2.662(2) 2 ? C2 N6 1.325(3) . ? C2 N5 1.375(3) . ? N5 H1 0.83(3) . ? O2 H3 0.70(6) . ? O2 H2 0.61(15) . ? 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 N1 Mn1 N1 180.0 . 3_565 ? N1 Mn1 N6 79.29(6) . . ? N1 Mn1 N6 100.71(6) 3_565 . ? N1 Mn1 N6 100.71(6) . 3_565 ? N1 Mn1 N6 79.29(6) 3_565 3_565 ? N6 Mn1 N6 180.00(6) . 3_565 ? N1 Mn1 N9 87.21(7) . 4_575 ? N1 Mn1 N9 92.79(7) 3_565 4_575 ? N6 Mn1 N9 88.24(7) . 4_575 ? N6 Mn1 N9 91.76(7) 3_565 4_575 ? N1 Mn1 N9 92.79(7) . 2_545 ? N1 Mn1 N9 87.21(7) 3_565 2_545 ? N6 Mn1 N9 91.76(7) . 2_545 ? N6 Mn1 N9 88.24(7) 3_565 2_545 ? N9 Mn1 N9 180.00(6) 4_575 2_545 ? O2 Na1 N2 166.09(10) . . ? O2 Na1 N3 90.83(10) . 3_665 ? N2 Na1 N3 95.35(7) . 3_665 ? O2 Na1 N8 78.52(9) . 2_545 ? N2 Na1 N8 93.41(7) . 2_545 ? N3 Na1 N8 166.70(7) 3_665 2_545 ? O2 Na1 N4 94.67(10) . 2_645 ? N2 Na1 N4 97.66(7) . 2_645 ? N3 Na1 N4 91.02(7) 3_665 2_645 ? N8 Na1 N4 97.72(7) 2_545 2_645 ? O2 Na1 N7 90.82(10) . 3_565 ? N2 Na1 N7 77.60(6) . 3_565 ? N3 Na1 N7 83.18(7) 3_665 3_565 ? N8 Na1 N7 88.96(6) 2_545 3_565 ? N4 Na1 N7 172.08(7) 2_645 3_565 ? N3 N2 N1 108.95(17) . . ? N3 N2 Na1 133.94(14) . . ? N1 N2 Na1 113.71(13) . . ? C1 N1 N2 104.32(16) . . ? C1 N1 Mn1 125.44(14) . . ? N2 N1 Mn1 125.02(13) . . ? N2 N3 N4 110.30(18) . . ? N2 N3 Na1 115.97(15) . 3_665 ? N4 N3 Na1 126.18(15) . 3_665 ? C1 N4 N3 103.73(18) . . ? C1 N4 Na1 123.72(16) . 2_655 ? N3 N4 Na1 95.52(14) . 2_655 ? N4 C1 N1 112.70(19) . . ? N4 C1 N5 122.2(2) . . ? N1 C1 N5 125.07(19) . . ? N8 N7 N6 109.16(16) . . ? N8 N7 Na1 100.96(13) . 3_565 ? N6 N7 Na1 99.54(12) . 3_565 ? C2 N9 N8 105.13(17) . . ? C2 N9 Mn1 134.77(14) . 2 ? N8 N9 Mn1 119.06(13) . 2 ? N7 N8 N9 109.24(17) . . ? N7 N8 Na1 125.90(13) . 2 ? N9 N8 Na1 124.82(13) . 2 ? N6 C2 N9 111.64(18) . . ? N6 C2 N5 125.87(19) . . ? N9 C2 N5 122.48(19) . . ? C2 N6 N7 104.83(16) . . ? C2 N6 Mn1 127.35(14) . . ? N7 N6 Mn1 126.69(13) . . ? C2 N5 C1 125.0(2) . . ? C2 N5 H1 118.1(19) . . ? C1 N5 H1 116.1(19) . . ? Na1 O2 H3 113(5) . . ? Na1 O2 H2 130(10) . . ? H3 O2 H2 117(10) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.316 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.086 data_mn _database_code_depnum_ccdc_archive 'CCDC 692764' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H32 Mn7 N54 O14' _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 Hexagonal _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 14.3137(3) _cell_length_b 14.3137(3) _cell_length_c 13.7292(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2436.01(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1878 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 27.520 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.239 _exptl_crystal_size_mid 0.193 _exptl_crystal_size_min 0.120 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1522 _exptl_absorpt_coefficient_mu 1.872 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_T_max 0.799 _exptl_absorpt_process_details SADABS _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 none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 11729 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1870 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+1.6695P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0056(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1870 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.299792(18) 0.502236(18) 0.149714(17) 0.01712(11) Uani 1 1 d . . . Mn2 Mn 0.0000 0.0000 0.0000 0.01603(14) Uani 1 6 d S . . O1 O 0.3333 0.6667 0.18262(14) 0.0167(4) Uani 1 3 d S . . O2 O 0.31301(12) 0.54142(12) -0.00833(10) 0.0271(3) Uani 1 1 d . . . O3 O 0.31333(10) 0.48321(10) 0.30737(9) 0.0243(3) Uani 1 1 d . . . N7 N 0.53194(12) 0.51718(11) 0.12787(11) 0.0249(3) Uani 1 1 d . . . N3 N 0.22366(11) 0.31830(11) 0.13132(10) 0.0207(3) Uani 1 1 d . . . N5 N 0.21323(12) 0.16340(11) 0.10606(11) 0.0231(3) Uani 1 1 d . . . N4 N 0.27865(11) 0.26334(12) 0.12727(11) 0.0244(3) Uani 1 1 d . . . N8 N 0.63761(11) 0.58764(11) 0.11620(11) 0.0239(3) Uani 1 1 d . . . N6 N 0.11197(11) 0.14682(11) 0.09382(11) 0.0212(3) Uani 1 1 d . . . N2 N 0.47980(11) 0.56865(11) 0.13973(10) 0.0209(3) Uani 1 1 d . . . N1 N 0.12641(10) 0.44999(10) 0.13644(10) 0.0191(3) Uani 1 1 d . . . C1 C 0.64542(12) 0.68398(13) 0.12147(11) 0.0175(3) Uani 1 1 d . . . N9 N 0.74261(11) 0.77699(11) 0.11230(12) 0.0245(3) Uani 1 1 d . . . C2 C 0.75672(12) 0.87871(13) 0.11215(11) 0.0181(3) Uani 1 1 d . . . H1 H 0.314(2) 0.498(2) -0.043(2) 0.044(7) Uiso 1 1 d . . . H2 H 0.274(3) 0.554(2) -0.026(2) 0.061(10) Uiso 1 1 d . . . H3 H 0.286(2) 0.417(2) 0.3262(18) 0.043(7) Uiso 1 1 d . . . H4 H 0.374(3) 0.508(3) 0.329(2) 0.068(10) 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 0.01210(14) 0.01227(14) 0.02578(16) -0.00042(9) -0.00074(9) 0.00518(10) Mn2 0.01054(18) 0.01054(18) 0.0270(3) 0.000 0.000 0.00527(9) O1 0.0133(5) 0.0133(5) 0.0233(9) 0.000 0.000 0.0067(3) O2 0.0297(7) 0.0306(7) 0.0282(6) -0.0026(6) -0.0004(5) 0.0205(6) O3 0.0203(6) 0.0202(6) 0.0288(6) 0.0034(5) -0.0013(5) 0.0075(5) N7 0.0192(7) 0.0163(7) 0.0393(8) 0.0038(6) 0.0061(6) 0.0090(6) N3 0.0163(6) 0.0149(6) 0.0317(7) -0.0036(5) -0.0050(5) 0.0084(5) N5 0.0184(7) 0.0170(7) 0.0358(8) -0.0039(6) -0.0072(6) 0.0104(6) N4 0.0196(7) 0.0181(7) 0.0380(8) -0.0054(6) -0.0080(6) 0.0114(6) N8 0.0170(7) 0.0161(7) 0.0397(8) 0.0039(6) 0.0065(6) 0.0092(5) N6 0.0165(6) 0.0141(6) 0.0333(7) -0.0024(5) -0.0036(6) 0.0079(5) N2 0.0158(6) 0.0144(6) 0.0315(7) 0.0025(5) 0.0024(5) 0.0067(5) N1 0.0144(6) 0.0119(6) 0.0308(7) -0.0022(5) -0.0010(5) 0.0066(5) C1 0.0140(7) 0.0156(7) 0.0237(7) 0.0024(6) 0.0021(6) 0.0079(6) N9 0.0119(6) 0.0147(7) 0.0468(9) 0.0030(6) 0.0044(6) 0.0065(5) C2 0.0125(7) 0.0159(7) 0.0249(7) -0.0002(6) 0.0011(6) 0.0062(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 2.1999(13) . ? Mn1 O1 2.2012(5) . ? Mn1 N1 2.2129(13) . ? Mn1 O2 2.2231(14) . ? Mn1 N2 2.2613(13) . ? Mn1 N3 2.3056(14) . ? Mn2 N6 2.2965(14) . ? Mn2 N6 2.2965(14) 7 ? Mn2 N6 2.2965(14) 2 ? Mn2 N6 2.2965(14) 3 ? Mn2 N6 2.2965(14) 9 ? Mn2 N6 2.2965(14) 8 ? O1 Mn1 2.2012(5) 3_565 ? O1 Mn1 2.2012(5) 2_665 ? N7 N2 1.295(2) . ? N7 N8 1.3438(19) . ? N3 C2 1.333(2) 3_565 ? N3 N4 1.3643(19) . ? N5 N4 1.292(2) . ? N5 N6 1.3572(19) . ? N8 C1 1.329(2) . ? N6 C2 1.339(2) 3_565 ? N2 N1 1.3572(18) 2_665 ? N1 C1 1.331(2) 3_565 ? N1 N2 1.3572(18) 3_565 ? C1 N1 1.331(2) 2_665 ? C1 N9 1.368(2) . ? N9 C2 1.367(2) . ? C2 N3 1.333(2) 2_665 ? C2 N6 1.339(2) 2_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O1 86.86(6) . . ? O3 Mn1 N1 101.09(5) . . ? O1 Mn1 N1 89.22(3) . . ? O3 Mn1 O2 171.05(5) . . ? O1 Mn1 O2 89.11(6) . . ? N1 Mn1 O2 86.82(5) . . ? O3 Mn1 N2 87.66(5) . . ? O1 Mn1 N2 88.25(4) . . ? N1 Mn1 N2 170.74(5) . . ? O2 Mn1 N2 84.23(5) . . ? O3 Mn1 N3 89.24(5) . . ? O1 Mn1 N3 165.85(4) . . ? N1 Mn1 N3 78.18(5) . . ? O2 Mn1 N3 96.52(5) . . ? N2 Mn1 N3 105.20(5) . . ? N6 Mn2 N6 180.00(9) . 7 ? N6 Mn2 N6 91.67(5) . 2 ? N6 Mn2 N6 88.33(5) 7 2 ? N6 Mn2 N6 91.67(5) . 3 ? N6 Mn2 N6 88.33(5) 7 3 ? N6 Mn2 N6 91.67(5) 2 3 ? N6 Mn2 N6 88.33(5) . 9 ? N6 Mn2 N6 91.67(5) 7 9 ? N6 Mn2 N6 88.33(5) 2 9 ? N6 Mn2 N6 180.00(8) 3 9 ? N6 Mn2 N6 88.33(5) . 8 ? N6 Mn2 N6 91.67(5) 7 8 ? N6 Mn2 N6 180.00(9) 2 8 ? N6 Mn2 N6 88.33(5) 3 8 ? N6 Mn2 N6 91.67(5) 9 8 ? Mn1 O1 Mn1 115.91(3) 3_565 2_665 ? Mn1 O1 Mn1 115.91(3) 3_565 . ? Mn1 O1 Mn1 115.91(3) 2_665 . ? N2 N7 N8 109.93(13) . . ? C2 N3 N4 103.87(13) 3_565 . ? C2 N3 Mn1 130.08(11) 3_565 . ? N4 N3 Mn1 125.70(10) . . ? N4 N5 N6 109.94(13) . . ? N5 N4 N3 109.88(13) . . ? C1 N8 N7 104.57(13) . . ? C2 N6 N5 104.01(13) 3_565 . ? C2 N6 Mn2 135.64(11) 3_565 . ? N5 N6 Mn2 115.16(10) . . ? N7 N2 N1 109.43(12) . 2_665 ? N7 N2 Mn1 128.93(11) . . ? N1 N2 Mn1 121.37(10) 2_665 . ? C1 N1 N2 104.13(12) 3_565 3_565 ? C1 N1 Mn1 133.17(11) 3_565 . ? N2 N1 Mn1 122.66(10) 3_565 . ? N8 C1 N1 111.94(14) . 2_665 ? N8 C1 N9 121.47(14) . . ? N1 C1 N9 126.59(14) 2_665 . ? C2 N9 C1 125.02(14) . . ? N3 C2 N6 112.26(14) 2_665 2_665 ? N3 C2 N9 126.41(14) 2_665 . ? N6 C2 N9 121.32(14) 2_665 . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.828 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.063