# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1038875_t4_0s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Mn N2 O2' _chemical_formula_weight 169.05 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 ? _symmetry_space_group_name_H-M ? 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 12.3034(4) _cell_length_b 12.4408(4) _cell_length_c 12.8156(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.190(2) _cell_angle_gamma 90.00 _cell_volume 1961.19(11) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 1.942 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5934 _exptl_absorpt_correction_T_max 0.7727 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20976 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.37 _reflns_number_total 4899 _reflns_number_gt 3131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0670P)^2^+1.7310P] 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 4899 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.173 _refine_ls_shift/su_mean 0.006 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 C1 C 0.7192(3) 0.50276(19) 0.0229(2) 0.0325(6) Uani 1 1 d . . . C4 C 0.7748(3) 0.00123(18) -0.0131(2) 0.0291(6) Uani 1 1 d . . . C3 C 0.7369(3) 0.2711(3) -0.2447(2) 0.0331(6) Uani 1 1 d . . . C2 C 0.7528(3) 0.7808(3) 0.2415(2) 0.0328(6) Uani 1 1 d . . . C5 C 1.0105(2) 0.7174(2) -0.0035(2) 0.0314(6) Uani 1 1 d . . . C6 C 0.4925(3) 0.2295(3) 0.0432(3) 0.0378(7) Uani 1 1 d . . . N1 N 0.5477(2) 0.4590(2) 0.8257(2) 0.0471(7) Uani 1 1 d . . . N2 N 0.4440(3) 0.4508(3) 0.6928(2) 0.0562(8) Uani 1 1 d . . . N3 N 0.5465(3) 0.0780(2) 0.7844(2) 0.0459(7) Uani 1 1 d . . . N4 N 0.4718(3) -0.0451(2) 0.6918(2) 0.0496(8) Uani 1 1 d . . . C8 C 0.4606(3) 0.0395(3) 0.8369(3) 0.0470(8) Uani 1 1 d . . . C9 C 0.5520(4) 0.0250(3) 0.6954(3) 0.0544(9) Uani 1 1 d . . . C7 C 0.4143(3) -0.0365(3) 0.7786(3) 0.0495(8) Uani 1 1 d . . . C10 C 0.5746(3) 0.5409(3) 0.7628(3) 0.0561(9) Uani 1 1 d . . . C11 C 0.5097(4) 0.5362(4) 0.6787(3) 0.0623(11) Uani 1 1 d . . . C12 C 0.4686(3) 0.4066(3) 0.7815(3) 0.0548(9) Uani 1 1 d . . . H3 H 0.790(3) 0.326(3) -0.241(3) 0.059(11) Uiso 1 1 d . . . H6 H 0.797(3) 0.833(3) 0.244(3) 0.073(13) Uiso 1 1 d . . . H5 H 1.005(3) 0.771(3) -0.062(3) 0.058(10) Uiso 1 1 d . . . H2 H 0.496(3) 0.305(4) 0.077(3) 0.091(14) Uiso 1 1 d . . . H4 H 0.779(4) 0.504(3) 0.073(4) 0.098(16) Uiso 1 1 d . . . H1 H 0.710(4) -0.004(3) -0.059(4) 0.097(16) Uiso 1 1 d . . . H15 H 0.630(3) 0.584(3) 0.776(3) 0.070(12) Uiso 1 1 d . . . H16 H 0.584(4) 0.444(4) 0.891(4) 0.102(16) Uiso 1 1 d . . . H7 H 0.354(4) -0.079(3) 0.786(3) 0.082(14) Uiso 1 1 d . . . H12 H 0.438(4) 0.352(4) 0.806(4) 0.102(17) Uiso 1 1 d . . . H11 H 0.449(3) 0.065(3) 0.901(3) 0.070(12) Uiso 1 1 d . . . H10 H 0.599(4) 0.129(4) 0.803(3) 0.097(15) Uiso 1 1 d . . . H13 H 0.393(5) 0.440(5) 0.644(5) 0.15(2) Uiso 1 1 d . . . H8 H 0.464(4) -0.097(4) 0.645(4) 0.117(18) Uiso 1 1 d . . . H14 H 0.495(4) 0.580(4) 0.623(4) 0.113(18) Uiso 1 1 d . . . H9 H 0.606(4) 0.036(4) 0.655(3) 0.095(16) Uiso 1 1 d . . . Mn1 Mn 0.74030(3) 0.25281(2) 0.00780(3) 0.01907(12) Uani 1 1 d . . . Mn2 Mn 0.75929(3) 0.75241(2) -0.00653(2) 0.01891(12) Uani 1 1 d . . . O1 O 0.57821(16) 0.19195(16) 0.01782(17) 0.0423(5) Uani 1 1 d . . . O7 O 0.92170(15) 0.68697(15) 0.02970(15) 0.0343(4) Uani 1 1 d . . . O5 O 0.80603(16) 0.09038(13) 0.01845(15) 0.0344(5) Uani 1 1 d . . . O4 O 0.89966(16) 0.31683(16) -0.02520(16) 0.0393(5) Uani 1 1 d . . . O8 O 0.59863(17) 0.81177(17) -0.03794(19) 0.0489(6) Uani 1 1 d . . . O2 O 0.7069(2) 0.23381(17) -0.16005(15) 0.0440(6) Uani 1 1 d . . . O9 O 0.81761(17) 0.91445(14) 0.00940(16) 0.0396(5) Uani 1 1 d . . . O3 O 0.67444(16) 0.41515(13) 0.00262(16) 0.0363(5) Uani 1 1 d . . . O12 O 0.7975(2) 0.74079(18) -0.17021(15) 0.0513(6) Uani 1 1 d . . . O11 O 0.7275(2) 0.74059(18) 0.15771(16) 0.0533(7) Uani 1 1 d . . . O6 O 0.7789(2) 0.25103(17) 0.17254(15) 0.0498(7) Uani 1 1 d . . . O10 O 0.69965(19) 0.58790(14) -0.02024(17) 0.0451(5) 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 C1 0.0336(16) 0.0257(13) 0.0376(14) -0.0031(10) -0.0123(13) -0.0023(11) C4 0.0334(16) 0.0242(13) 0.0295(13) 0.0001(9) -0.0052(11) -0.0010(11) C3 0.0375(18) 0.0364(14) 0.0256(13) 0.0001(10) 0.0019(12) -0.0029(13) C2 0.0399(18) 0.0335(14) 0.0249(13) 0.0033(10) 0.0004(12) -0.0049(13) C5 0.0269(16) 0.0314(13) 0.0360(14) 0.0092(11) 0.0004(12) -0.0034(12) C6 0.0247(16) 0.0364(14) 0.0524(18) -0.0024(13) 0.0032(13) -0.0011(13) N1 0.0458(18) 0.0554(17) 0.0396(14) -0.0042(12) -0.0105(13) 0.0032(14) N2 0.0434(19) 0.072(2) 0.0522(17) -0.0236(16) -0.0187(15) 0.0123(16) N3 0.0478(19) 0.0379(14) 0.0514(16) -0.0046(12) -0.0076(14) -0.0077(13) N4 0.064(2) 0.0394(14) 0.0450(15) -0.0155(12) -0.0124(14) 0.0017(14) C8 0.055(2) 0.0490(18) 0.0369(16) -0.0082(14) 0.0034(15) -0.0083(17) C9 0.056(3) 0.066(2) 0.0415(18) 0.0038(17) 0.0114(17) 0.004(2) C7 0.055(2) 0.0422(17) 0.0510(19) 0.0005(15) -0.0017(17) -0.0111(17) C10 0.047(2) 0.050(2) 0.070(2) -0.0039(18) -0.0059(19) -0.0121(18) C11 0.068(3) 0.067(2) 0.052(2) 0.0128(19) 0.000(2) 0.004(2) C12 0.049(2) 0.0465(19) 0.069(2) -0.0006(18) 0.0008(19) -0.0074(18) Mn1 0.0205(2) 0.01872(19) 0.01794(18) 0.00091(12) -0.00126(14) 0.00022(14) Mn2 0.0210(2) 0.01841(19) 0.01724(18) -0.00020(12) -0.00009(14) -0.00096(14) O1 0.0239(11) 0.0375(11) 0.0660(14) -0.0050(10) 0.0091(10) -0.0054(9) O7 0.0239(10) 0.0386(10) 0.0403(10) 0.0143(8) 0.0012(8) 0.0010(8) O5 0.0378(12) 0.0205(8) 0.0445(11) -0.0045(8) -0.0113(9) 0.0046(8) O4 0.0235(11) 0.0430(11) 0.0516(12) 0.0147(9) 0.0027(9) -0.0022(9) O8 0.0239(12) 0.0414(11) 0.0811(16) 0.0052(11) -0.0023(11) 0.0009(10) O2 0.0582(16) 0.0533(12) 0.0202(9) 0.0012(8) -0.0020(9) -0.0090(11) O9 0.0390(13) 0.0192(9) 0.0601(13) 0.0009(8) -0.0099(10) -0.0021(8) O3 0.0352(12) 0.0189(8) 0.0542(12) -0.0010(8) -0.0114(9) 0.0012(8) O12 0.0655(18) 0.0700(15) 0.0186(9) 0.0014(9) 0.0039(10) 0.0199(12) O11 0.074(2) 0.0642(15) 0.0217(10) -0.0011(9) 0.0099(10) -0.0185(12) O6 0.0638(18) 0.0659(16) 0.0196(10) -0.0026(9) -0.0024(10) 0.0112(11) O10 0.0579(15) 0.0228(9) 0.0536(12) 0.0045(9) -0.0205(11) -0.0098(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 C1 O10 1.217(3) . ? C1 O3 1.246(3) . ? C4 O9 1.233(3) 1_545 ? C4 O5 1.239(3) . ? C3 O12 1.222(3) 2_644 ? C3 O2 1.243(3) . ? C2 O11 1.219(3) . ? C2 O6 1.234(3) 2_655 ? C5 O4 1.234(3) 3_765 ? C5 O7 1.240(3) . ? C6 O1 1.205(4) . ? C6 O8 1.233(4) 3_665 ? N1 C12 1.292(5) . ? N1 C10 1.345(5) . ? N2 C12 1.293(5) . ? N2 C11 1.350(5) . ? N3 C9 1.321(4) . ? N3 C8 1.352(4) . ? N4 C9 1.318(5) . ? N4 C7 1.336(5) . ? C8 C7 1.326(5) . ? C10 C11 1.329(6) . ? Mn1 O1 2.139(2) . ? Mn1 O6 2.155(2) . ? Mn1 O4 2.1661(19) . ? Mn1 O3 2.1766(17) . ? Mn1 O5 2.1798(17) . ? Mn1 O2 2.1944(19) . ? Mn2 O8 2.141(2) . ? Mn2 O9 2.1480(18) . ? Mn2 O11 2.154(2) . ? Mn2 O12 2.1640(19) . ? Mn2 O10 2.1801(18) . ? Mn2 O7 2.1983(19) . ? O4 C5 1.234(3) 3_765 ? O8 C6 1.233(4) 3_665 ? O9 C4 1.233(3) 1_565 ? O12 C3 1.222(3) 2_654 ? O6 C2 1.234(3) 2_645 ? 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 O10 C1 O3 125.8(3) . . ? O9 C4 O5 125.4(3) 1_545 . ? O12 C3 O2 124.1(3) 2_644 . ? O11 C2 O6 125.7(3) . 2_655 ? O4 C5 O7 125.6(3) 3_765 . ? O1 C6 O8 128.6(3) . 3_665 ? C12 N1 C10 108.2(3) . . ? C12 N2 C11 108.8(3) . . ? C9 N3 C8 107.9(3) . . ? C9 N4 C7 109.0(3) . . ? C7 C8 N3 107.7(3) . . ? N3 C9 N4 108.0(3) . . ? C8 C7 N4 107.4(3) . . ? C11 C10 N1 107.5(4) . . ? C10 C11 N2 106.1(4) . . ? N2 C12 N1 109.4(4) . . ? O1 Mn1 O6 97.16(9) . . ? O1 Mn1 O4 172.09(8) . . ? O6 Mn1 O4 90.74(9) . . ? O1 Mn1 O3 89.05(8) . . ? O6 Mn1 O3 96.54(8) . . ? O4 Mn1 O3 89.47(8) . . ? O1 Mn1 O5 90.76(8) . . ? O6 Mn1 O5 81.67(8) . . ? O4 Mn1 O5 90.97(8) . . ? O3 Mn1 O5 178.15(7) . . ? O1 Mn1 O2 82.24(9) . . ? O6 Mn1 O2 172.97(8) . . ? O4 Mn1 O2 90.00(8) . . ? O3 Mn1 O2 90.46(8) . . ? O5 Mn1 O2 91.33(8) . . ? O8 Mn2 O9 89.97(8) . . ? O8 Mn2 O11 91.22(10) . . ? O9 Mn2 O11 92.20(8) . . ? O8 Mn2 O12 93.39(10) . . ? O9 Mn2 O12 94.36(9) . . ? O11 Mn2 O12 171.98(9) . . ? O8 Mn2 O10 90.04(8) . . ? O9 Mn2 O10 179.16(8) . . ? O11 Mn2 O10 86.96(8) . . ? O12 Mn2 O10 86.49(9) . . ? O8 Mn2 O7 177.85(7) . . ? O9 Mn2 O7 91.56(8) . . ? O11 Mn2 O7 87.21(9) . . ? O12 Mn2 O7 88.00(8) . . ? O10 Mn2 O7 88.41(8) . . ? C6 O1 Mn1 134.5(2) . . ? C5 O7 Mn2 128.16(18) . . ? C4 O5 Mn1 134.20(19) . . ? C5 O4 Mn1 128.61(18) 3_765 . ? C6 O8 Mn2 134.5(2) 3_665 . ? C3 O2 Mn1 139.7(2) . . ? C4 O9 Mn2 131.23(19) 1_565 . ? C1 O3 Mn1 130.00(19) . . ? C3 O12 Mn2 140.0(2) 2_654 . ? C2 O11 Mn2 141.6(2) . . ? C2 O6 Mn1 143.6(2) 2_645 . ? C1 O10 Mn2 135.87(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.739 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 959632' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1038874_b4_0s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Mn2 N4 O12' _chemical_formula_weight 518.17 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 12.1962(3) _cell_length_b 12.3675(3) _cell_length_c 12.8155(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.4280(10) _cell_angle_gamma 90.00 _cell_volume 1932.44(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5164 _cell_measurement_theta_min 6.360 _cell_measurement_theta_max 56.885 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 1.971 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5893 _exptl_absorpt_correction_T_max 0.7699 _exptl_absorpt_process_details 'SADABS Version 2008/1 (Sheldrick, Bruker AXS Inc.)' _exptl_special_details ; Data was collected using a X8 APEX II BRUKER-NONIUS diffractometer equipped with an KYROFLEX low-temperature apparatus operating at 100 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.5\% per frame for 5 s , such that a total of 5054 frames were collected in a optimized strategy and with a final resolution of 0.75 \%A. Data integration and reduction was performed using the Apex2, Bruker Instrument Service v2010, 1-2 suite software. Absorption corrections were applied using SADABS Version 2008/1 (Sheldrick, Bruker AXS Inc.) of the suite software. The structures are solved by the direct method using the SHELX-97 program and refined by least squares method on F2 SHELXL-97, incorporated in the Apex2 suite software. ; _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 'APEXII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 20812 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.47 _reflns_number_total 4863 _reflns_number_gt 3904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2, Bruker Instrument Service v2010, 1-2' _computing_cell_refinement ' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.' _computing_data_reduction 'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)' _computing_structure_solution 'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) ' _computing_structure_refinement 'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0400P)^2^+1.4855P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_number_reflns 4863 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 C7 C 0.24590(19) 0.28245(16) 0.26199(15) 0.0132(4) Uani 1 1 d . . . C10 C 0.72439(18) -0.00233(15) 0.01267(15) 0.0118(4) Uani 1 1 d . . . C8 C 0.23006(18) 0.27129(16) -0.24181(15) 0.0128(4) Uani 1 1 d . . . C11 C 0.78496(18) 0.49548(15) -0.02580(16) 0.0137(4) Uani 1 1 d . . . C12 C 0.98699(19) 0.23116(17) 0.04883(16) 0.0145(4) Uani 1 1 d . . . C9 C 0.48335(18) 0.28929(16) 0.00525(15) 0.0132(4) Uani 1 1 d . . . H4 H 0.489(2) 0.2370(18) 0.0627(19) 0.012(6) Uiso 1 1 d . . . H1 H 0.989(2) 0.310(2) 0.071(2) 0.023(7) Uiso 1 1 d . . . H5 H 0.189(2) 0.339(2) 0.262(2) 0.029(7) Uiso 1 1 d . . . H6 H 0.288(2) 0.330(2) -0.237(2) 0.023(7) Uiso 1 1 d . . . H3 H 0.731(3) 0.492(2) -0.090(2) 0.040(9) Uiso 1 1 d . . . H2 H 0.788(3) 0.001(2) 0.062(3) 0.046(9) Uiso 1 1 d . . . H15 H 0.640(2) -0.0889(19) 0.2826(18) 0.013(6) Uiso 1 1 d . . . H13 H 0.427(2) 0.149(2) 0.3050(19) 0.020(6) Uiso 1 1 d . . . H16 H 0.513(2) -0.0819(19) 0.1160(19) 0.017(6) Uiso 1 1 d . . . 10 H 0.062(2) -0.063(2) 0.093(2) 0.022(7) Uiso 1 1 d . . . H14 H 0.579(2) 0.054(2) 0.384(2) 0.027(7) Uiso 1 1 d . . . H11 H 0.151(2) 0.081(2) 0.2104(19) 0.020(6) Uiso 1 1 d . . . H17 H 0.398(2) 0.063(2) 0.137(2) 0.028(7) Uiso 1 1 d . . . H7 H -0.090(2) -0.125(2) 0.196(2) 0.030(8) Uiso 1 1 d . . . H9 H 0.039(2) 0.088(2) 0.359(2) 0.025(7) Uiso 1 1 d . . . H8 H -0.105(2) -0.037(2) 0.352(2) 0.034(8) Uiso 1 1 d . . . Mn1 Mn 0.23534(3) 0.25497(2) 0.01177(2) 0.00779(9) Uani 1 1 d . . . Mn2 Mn 0.73602(3) 0.24709(2) 0.01000(2) 0.00760(9) Uani 1 1 d . . . O7 O 0.19909(13) 0.23455(11) -0.15586(11) 0.0151(3) Uani 1 1 d . . . O1 O 0.57443(12) 0.31667(11) -0.03031(11) 0.0134(3) Uani 1 1 d . . . O4 O 0.89582(12) 0.18502(11) 0.04892(11) 0.0146(3) Uani 1 1 d . . . O9 O 0.07455(12) 0.18937(11) 0.02342(11) 0.0152(3) Uani 1 1 d . . . O6 O 0.77457(14) 0.25883(12) -0.15288(11) 0.0181(3) Uani 1 1 d . . . O10 O 0.16488(12) 0.41685(10) 0.00725(11) 0.0134(3) Uani 1 1 d . . . O12 O 0.39312(12) 0.32397(11) -0.02612(11) 0.0148(3) Uani 1 1 d . . . O5 O 0.67647(13) 0.08408(11) -0.00927(11) 0.0145(3) Uani 1 1 d . . . O2 O 0.69194(14) 0.25902(12) 0.17234(11) 0.0180(3) Uani 1 1 d . . . O8 O 0.30687(12) 0.09358(11) 0.02114(11) 0.0134(3) Uani 1 1 d . . . O11 O 0.28081(14) 0.25435(11) 0.17541(11) 0.0177(3) Uani 1 1 d . . . O3 O 0.79731(14) 0.41199(11) 0.02574(11) 0.0180(3) Uani 1 1 d . . . C6 C 0.09183(19) 0.03672(17) 0.21873(16) 0.0156(4) Uani 1 1 d . . . N4 N -0.04255(16) -0.08014(14) 0.21105(13) 0.0145(4) Uani 1 1 d . . . C4 C 0.04468(19) -0.03999(17) 0.15755(16) 0.0158(4) Uani 1 1 d . . . N5 N 0.03154(16) 0.04281(14) 0.30784(13) 0.0151(4) Uani 1 1 d . . . C5 C -0.04910(19) -0.02852(17) 0.30144(16) 0.0165(4) Uani 1 1 d . . . N2 N 0.44745(16) 0.04664(14) 0.18644(13) 0.0156(4) Uani 1 1 d . . . N1 N 0.54935(16) 0.04020(14) 0.32534(14) 0.0152(4) Uani 1 1 d . . . C2 C 0.5821(2) -0.04245(17) 0.26157(16) 0.0177(4) Uani 1 1 d . . . C1 C 0.46793(19) 0.09298(17) 0.27819(16) 0.0164(4) Uani 1 1 d . . . C3 C 0.5183(2) -0.03821(17) 0.17452(16) 0.0184(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 C7 0.0153(11) 0.0128(9) 0.0116(9) -0.0012(7) 0.0005(8) 0.0004(8) C10 0.0130(11) 0.0110(9) 0.0114(8) 0.0006(6) -0.0001(8) -0.0005(7) C8 0.0139(11) 0.0129(8) 0.0116(9) -0.0002(7) 0.0003(8) 0.0005(8) C11 0.0138(11) 0.0116(9) 0.0157(9) -0.0005(7) -0.0021(8) 0.0002(8) C12 0.0134(11) 0.0159(9) 0.0143(9) -0.0008(7) 0.0005(8) -0.0002(8) C9 0.0141(11) 0.0114(9) 0.0140(9) 0.0018(7) -0.0011(8) -0.0005(8) Mn1 0.00887(17) 0.00743(14) 0.00706(14) 0.00018(9) -0.00006(11) -0.00015(11) Mn2 0.00903(17) 0.00712(14) 0.00667(14) 0.00000(9) 0.00021(11) -0.00023(11) O7 0.0194(9) 0.0171(7) 0.0088(6) 0.0006(5) -0.0004(6) -0.0031(6) O1 0.0111(8) 0.0151(6) 0.0141(6) 0.0046(5) 0.0005(6) 0.0009(6) O4 0.0105(8) 0.0146(7) 0.0187(7) 0.0004(5) -0.0004(6) 0.0001(6) O9 0.0109(8) 0.0131(6) 0.0218(7) -0.0007(5) 0.0035(6) -0.0005(6) O6 0.0238(9) 0.0218(8) 0.0089(6) -0.0013(5) 0.0026(6) -0.0066(6) O10 0.0130(8) 0.0086(6) 0.0186(7) -0.0011(5) -0.0019(6) -0.0006(5) O12 0.0118(8) 0.0152(7) 0.0173(7) 0.0033(5) 0.0001(6) -0.0008(6) O5 0.0138(8) 0.0093(6) 0.0205(7) -0.0003(5) -0.0016(6) 0.0004(6) O2 0.0212(9) 0.0245(8) 0.0084(6) 0.0006(5) 0.0017(6) 0.0063(6) O8 0.0142(8) 0.0094(6) 0.0166(6) -0.0016(5) -0.0020(6) 0.0013(6) O11 0.0202(9) 0.0231(8) 0.0097(6) -0.0012(5) -0.0002(6) 0.0030(6) O3 0.0237(9) 0.0101(6) 0.0199(7) 0.0024(5) -0.0076(6) -0.0031(6) C6 0.0160(12) 0.0158(9) 0.0151(9) -0.0004(7) 0.0018(8) -0.0030(9) N4 0.0148(10) 0.0142(8) 0.0143(8) -0.0008(6) -0.0012(7) -0.0038(7) C4 0.0186(12) 0.0168(9) 0.0122(9) -0.0013(7) 0.0021(8) -0.0018(8) N5 0.0187(10) 0.0135(8) 0.0131(8) -0.0036(6) -0.0014(7) -0.0001(7) C5 0.0170(12) 0.0190(10) 0.0136(9) -0.0011(7) 0.0007(8) -0.0011(9) N2 0.0140(10) 0.0181(8) 0.0145(8) 0.0032(6) -0.0034(7) -0.0011(7) N1 0.0159(10) 0.0154(8) 0.0141(8) 0.0003(6) -0.0024(7) -0.0002(7) C2 0.0191(12) 0.0167(9) 0.0174(10) 0.0002(8) -0.0001(9) 0.0034(9) C1 0.0174(12) 0.0148(9) 0.0170(9) 0.0004(8) -0.0017(8) 0.0017(9) C3 0.0196(12) 0.0185(10) 0.0172(10) -0.0031(8) 0.0005(9) 0.0017(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 C7 O6 1.247(2) 4_566 ? C7 O11 1.248(2) . ? C10 O5 1.247(2) . ? C10 O8 1.264(2) 3_655 ? C8 O2 1.242(2) 4_565 ? C8 O7 1.258(2) . ? C11 O3 1.233(2) . ? C11 O10 1.265(2) 3_665 ? C12 O9 1.237(3) 1_655 ? C12 O4 1.250(3) . ? C9 O12 1.239(3) . ? C9 O1 1.258(3) . ? Mn1 O9 2.1309(15) . ? Mn1 O11 2.1559(15) . ? Mn1 O12 2.1710(15) . ? Mn1 O10 2.1789(14) . ? Mn1 O8 2.1804(13) . ? Mn1 O7 2.1970(14) . ? Mn2 O4 2.1420(15) . ? Mn2 O5 2.1549(14) . ? Mn2 O6 2.1560(14) . ? Mn2 O2 2.1668(14) . ? Mn2 O3 2.1798(14) . ? Mn2 O1 2.2001(15) . ? O9 C12 1.237(3) 1_455 ? O6 C7 1.247(2) 4_665 ? O10 C11 1.265(2) 3_665 ? O2 C8 1.242(2) 4_666 ? O8 C10 1.264(2) 3_655 ? C6 C4 1.350(3) . ? C6 N5 1.376(3) . ? N4 C5 1.327(3) . ? N4 C4 1.373(3) . ? N5 C5 1.322(3) . ? N2 C1 1.326(3) . ? N2 C3 1.370(3) . ? N1 C1 1.322(3) . ? N1 C2 1.374(3) . ? C2 C3 1.345(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 O6 C7 O11 124.7(2) 4_566 . ? O5 C10 O8 123.5(2) . 3_655 ? O2 C8 O7 123.6(2) 4_565 . ? O3 C11 O10 124.4(2) . 3_665 ? O9 C12 O4 125.7(2) 1_655 . ? O12 C9 O1 125.08(18) . . ? O9 Mn1 O11 98.36(6) . . ? O9 Mn1 O12 171.00(5) . . ? O11 Mn1 O12 90.63(6) . . ? O9 Mn1 O10 89.35(6) . . ? O11 Mn1 O10 96.94(5) . . ? O12 Mn1 O10 89.09(5) . . ? O9 Mn1 O8 90.87(6) . . ? O11 Mn1 O8 81.39(5) . . ? O12 Mn1 O8 90.95(5) . . ? O10 Mn1 O8 178.33(5) . . ? O9 Mn1 O7 82.05(6) . . ? O11 Mn1 O7 172.48(5) . . ? O12 Mn1 O7 89.10(6) . . ? O10 Mn1 O7 90.57(5) . . ? O8 Mn1 O7 91.10(5) . . ? O4 Mn2 O5 89.63(6) . . ? O4 Mn2 O6 91.75(6) . . ? O5 Mn2 O6 91.90(5) . . ? O4 Mn2 O2 92.69(6) . . ? O5 Mn2 O2 94.75(6) . . ? O6 Mn2 O2 172.03(6) . . ? O4 Mn2 O3 90.33(6) . . ? O5 Mn2 O3 178.68(6) . . ? O6 Mn2 O3 86.79(6) . . ? O2 Mn2 O3 86.57(6) . . ? O4 Mn2 O1 177.95(5) . . ? O5 Mn2 O1 92.39(6) . . ? O6 Mn2 O1 87.82(6) . . ? O2 Mn2 O1 87.51(6) . . ? O3 Mn2 O1 87.64(6) . . ? C8 O7 Mn1 139.20(14) . . ? C9 O1 Mn2 127.14(13) . . ? C12 O4 Mn2 129.83(14) . . ? C12 O9 Mn1 131.39(14) 1_455 . ? C7 O6 Mn2 139.16(14) 4_665 . ? C11 O10 Mn1 126.46(14) 3_665 . ? C9 O12 Mn1 125.20(13) . . ? C10 O5 Mn2 128.41(14) . . ? C8 O2 Mn2 137.21(15) 4_666 . ? C10 O8 Mn1 132.95(14) 3_655 . ? C7 O11 Mn1 141.15(15) . . ? C11 O3 Mn2 134.18(14) . . ? C4 C6 N5 106.97(19) . . ? C5 N4 C4 109.04(18) . . ? C6 C4 N4 106.76(18) . . ? C5 N5 C6 108.91(17) . . ? N5 C5 N4 108.32(19) . . ? C1 N2 C3 108.93(19) . . ? C1 N1 C2 108.76(18) . . ? C3 C2 N1 107.1(2) . . ? N1 C1 N2 108.34(19) . . ? C2 C3 N2 106.91(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.057 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 959633'