# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H22 Cd N12 O2' _chemical_formula_weight 430.79 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' Cd Cd -0.8075 1.2024 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.92830(10) _cell_length_b 13.3730(2) _cell_length_c 15.2752(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.2840(10) _cell_angle_gamma 90.00 _cell_volume 1582.48(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9430 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.610 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872.0 _exptl_absorpt_coefficient_mu 1.412 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.543 _exptl_absorpt_correction_T_max 0.561 _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 none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 24570 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.61 _reflns_number_total 3680 _reflns_number_gt 3241 _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^)+(0.0400P)^2^+4.0201P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3680 _refine_ls_number_parameters 220 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.967 _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 Cd1 Cd 0.51210(3) 0.352748(15) 0.283853(15) 0.03337(9) Uani 1 1 d . . . N1 N 0.5222(3) 0.52736(16) 0.33859(15) 0.0304(4) Uani 1 1 d U . . N2 N 0.5139(3) 0.68538(18) 0.31015(16) 0.0332(4) Uani 1 1 d U . . N3 N 0.4995(4) 0.67783(18) 0.39506(16) 0.0355(6) Uani 1 1 d . . . N4 N 0.4911(3) 0.54611(17) 0.49529(16) 0.0321(5) Uani 1 1 d . . . N5 N 0.2339(3) 0.33598(18) 0.30270(18) 0.0342(5) Uani 1 1 d . . . H5C H 0.1871 0.3967 0.3064 0.041 Uiso 1 1 d R . . H5D H 0.1699 0.3037 0.2554 0.041 Uiso 1 1 d R . . N6 N 0.5436(3) 0.24240(19) 0.40312(16) 0.0364(6) Uani 1 1 d . . . H6A H 0.6195 0.1939 0.3977 0.044 Uiso 1 1 d R . . H6B H 0.5821 0.2747 0.4552 0.044 Uiso 1 1 d R . . N7 N 0.4835(3) 0.41939(19) 0.14085(16) 0.0350(5) Uani 1 1 d . . . H7A H 0.4020 0.3858 0.1019 0.042 Uiso 1 1 d R . . H7B H 0.4518 0.4840 0.1406 0.042 Uiso 1 1 d R . . N8 N 0.7939(3) 0.36863(18) 0.26934(19) 0.0357(6) Uani 1 1 d . . . H8A H 0.8588 0.3945 0.3198 0.043 Uiso 1 1 d R . . H8B H 0.8370 0.3083 0.2598 0.043 Uiso 1 1 d R . . C1 C 0.5264(4) 0.59639(19) 0.27614(17) 0.0289(4) Uani 1 1 d U . . H1 H 0.5366 0.5835 0.2177 0.035 Uiso 1 1 calc R . . C2 C 0.5055(4) 0.58014(19) 0.41013(18) 0.0281(5) Uani 1 1 d . . . C3 C 0.2347(4) 0.2790(2) 0.3854(2) 0.0393(7) Uani 1 1 d . . . H3A H 0.1228 0.2478 0.3814 0.047 Uiso 1 1 calc R . . H3B H 0.2542 0.3244 0.4361 0.047 Uiso 1 1 calc R . . C4 C 0.3728(5) 0.1996(2) 0.4006(2) 0.0402(7) Uani 1 1 d . . . H4A H 0.3732 0.1657 0.4568 0.048 Uiso 1 1 calc R . . H4B H 0.3470 0.1505 0.3529 0.048 Uiso 1 1 calc R . . C5 C 0.6511(4) 0.4104(2) 0.1149(2) 0.0409(7) Uani 1 1 d . . . H5A H 0.6545 0.4556 0.0656 0.049 Uiso 1 1 calc R . . H5B H 0.6652 0.3427 0.0947 0.049 Uiso 1 1 calc R . . C6 C 0.7972(4) 0.4351(2) 0.1931(2) 0.0416(7) Uani 1 1 d . . . H6C H 0.9066 0.4278 0.1749 0.050 Uiso 1 1 calc R . . H6D H 0.7868 0.5040 0.2110 0.050 Uiso 1 1 calc R . . N9 N 0.9923(4) 0.1833(2) 0.0986(2) 0.0477(7) Uani 1 1 d . . . N10 N 0.9576(4) 0.1945(2) 0.17967(18) 0.0408(5) Uani 1 1 d U . . N11 N 0.9220(4) 0.03696(19) 0.14803(17) 0.0367(5) Uani 1 1 d U . . N12 N 0.9965(4) 0.04670(18) 0.00007(18) 0.0384(6) Uani 1 1 d . . . C7 C 0.9153(4) 0.1075(2) 0.2083(2) 0.0348(4) Uani 1 1 d U . . H7 H 0.8850 0.0967 0.2631 0.042 Uiso 1 1 calc R . . C8 C 0.9704(4) 0.0860(2) 0.0817(2) 0.0331(6) Uani 1 1 d . . . O1 O 0.0980(4) 0.37426(18) 0.04191(18) 0.0519(6) Uani 1 1 d . . . H10 H 0.0237 0.3977 0.0031 0.078 Uiso 1 1 d R . . H11 H 0.0696 0.3205 0.0565 0.078 Uiso 1 1 d R . . O2 O 0.1526(4) 0.5719(2) 0.11313(17) 0.0539(6) Uani 1 1 d . . . H2 H 0.2547 0.5798 0.1283 0.081 Uiso 1 1 d R . . H3 H 0.1245 0.5167 0.1014 0.081 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03279(14) 0.03041(13) 0.03865(14) 0.00696(8) 0.01154(9) 0.00091(8) N1 0.0466(11) 0.0217(8) 0.0252(9) 0.0018(7) 0.0127(8) 0.0002(8) N2 0.0509(11) 0.0232(9) 0.0268(9) 0.0033(8) 0.0110(8) -0.0003(8) N3 0.0575(16) 0.0230(11) 0.0270(12) 0.0008(9) 0.0109(11) 0.0014(11) N4 0.0476(15) 0.0226(10) 0.0272(11) -0.0001(9) 0.0103(10) 0.0009(10) N5 0.0312(13) 0.0304(12) 0.0410(14) -0.0028(10) 0.0080(11) -0.0016(10) N6 0.0467(15) 0.0343(13) 0.0293(12) -0.0007(10) 0.0107(11) 0.0108(11) N7 0.0374(14) 0.0340(13) 0.0330(13) -0.0022(10) 0.0059(10) -0.0028(10) N8 0.0297(13) 0.0303(12) 0.0467(15) -0.0065(11) 0.0072(11) 0.0015(10) C1 0.0470(10) 0.0202(8) 0.0223(8) 0.0025(7) 0.0137(8) -0.0003(7) C2 0.0375(15) 0.0224(12) 0.0252(13) 0.0007(10) 0.0084(11) -0.0003(10) C3 0.0410(17) 0.0429(17) 0.0373(16) -0.0050(13) 0.0158(13) -0.0051(13) C4 0.060(2) 0.0317(15) 0.0340(15) 0.0031(12) 0.0205(15) -0.0010(14) C5 0.0517(19) 0.0363(16) 0.0399(17) -0.0035(13) 0.0212(15) -0.0051(14) C6 0.0378(17) 0.0345(15) 0.057(2) -0.0033(14) 0.0192(15) -0.0050(13) N9 0.071(2) 0.0272(13) 0.0509(17) -0.0060(12) 0.0258(15) -0.0052(13) N10 0.0517(11) 0.0341(10) 0.0367(10) -0.0062(9) 0.0098(9) 0.0039(9) N11 0.0480(11) 0.0309(9) 0.0323(10) -0.0008(8) 0.0111(9) 0.0031(8) N12 0.0530(16) 0.0267(11) 0.0388(13) -0.0013(10) 0.0171(12) -0.0009(11) C7 0.0464(11) 0.0298(9) 0.0298(9) -0.0034(8) 0.0118(8) 0.0043(8) C8 0.0398(16) 0.0263(13) 0.0345(15) -0.0011(11) 0.0107(12) -0.0002(11) O1 0.0578(16) 0.0401(13) 0.0580(16) 0.0011(11) 0.0128(12) -0.0046(11) O2 0.0608(16) 0.0530(15) 0.0483(14) -0.0011(12) 0.0126(12) -0.0096(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N5 2.295(3) . ? Cd1 N8 2.301(3) . ? Cd1 N6 2.316(2) . ? Cd1 N7 2.325(2) . ? Cd1 N1 2.476(2) . ? Cd1 N2 2.644(2) 2_645 ? N1 C2 1.331(3) . ? N1 C1 1.333(3) . ? N2 C1 1.311(4) . ? N2 N3 1.330(3) . ? N2 Cd1 2.644(2) 2_655 ? N3 C2 1.326(3) . ? N4 N4 1.246(5) 3_666 ? N4 C2 1.405(4) . ? N5 C3 1.474(4) . ? N5 H5C 0.9000 . ? N5 H5D 0.9000 . ? N6 C4 1.463(4) . ? N6 H6A 0.9000 . ? N6 H6B 0.9000 . ? N7 C5 1.471(4) . ? N7 H7A 0.9000 . ? N7 H7B 0.9000 . ? N8 C6 1.470(4) . ? N8 H8A 0.9000 . ? N8 H8B 0.9000 . ? C1 H1 0.9300 . ? C3 C4 1.508(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.512(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6C 0.9700 . ? C6 H6D 0.9700 . ? N9 C8 1.330(4) . ? N9 N10 1.334(4) . ? N10 C7 1.312(4) . ? N11 C7 1.326(4) . ? N11 C8 1.331(4) . ? N12 N12 1.250(5) 3_755 ? N12 C8 1.408(4) . ? C7 H7 0.9300 . ? O1 H10 0.8044 . ? O1 H11 0.7999 . ? O2 H2 0.8004 . ? O2 H3 0.7798 . ? 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 N5 Cd1 N8 178.33(9) . . ? N5 Cd1 N6 77.57(9) . . ? N8 Cd1 N6 100.96(9) . . ? N5 Cd1 N7 104.53(9) . . ? N8 Cd1 N7 77.11(9) . . ? N6 Cd1 N7 162.88(9) . . ? N5 Cd1 N1 90.73(9) . . ? N8 Cd1 N1 89.03(9) . . ? N6 Cd1 N1 110.18(8) . . ? N7 Cd1 N1 86.87(8) . . ? N5 Cd1 N2 91.11(9) . 2_645 ? N8 Cd1 N2 89.48(8) . 2_645 ? N6 Cd1 N2 82.57(8) . 2_645 ? N7 Cd1 N2 80.41(8) . 2_645 ? N1 Cd1 N2 167.21(8) . 2_645 ? C2 N1 C1 104.0(2) . . ? C2 N1 Cd1 140.87(18) . . ? C1 N1 Cd1 114.54(17) . . ? C1 N2 N3 110.3(2) . . ? C1 N2 Cd1 123.86(18) . 2_655 ? N3 N2 Cd1 125.53(18) . 2_655 ? C2 N3 N2 103.7(2) . . ? N4 N4 C2 113.5(3) 3_666 . ? C3 N5 Cd1 109.22(19) . . ? C3 N5 H5C 109.9 . . ? Cd1 N5 H5C 109.8 . . ? C3 N5 H5D 109.8 . . ? Cd1 N5 H5D 109.8 . . ? H5C N5 H5D 108.3 . . ? C4 N6 Cd1 106.52(18) . . ? C4 N6 H6A 110.4 . . ? Cd1 N6 H6A 110.4 . . ? C4 N6 H6B 110.4 . . ? Cd1 N6 H6B 110.4 . . ? H6A N6 H6B 108.6 . . ? C5 N7 Cd1 107.97(19) . . ? C5 N7 H7A 110.1 . . ? Cd1 N7 H7A 110.1 . . ? C5 N7 H7B 110.2 . . ? Cd1 N7 H7B 110.1 . . ? H7A N7 H7B 108.4 . . ? C6 N8 Cd1 108.27(18) . . ? C6 N8 H8A 110.0 . . ? Cd1 N8 H8A 110.1 . . ? C6 N8 H8B 110.0 . . ? Cd1 N8 H8B 110.0 . . ? H8A N8 H8B 108.4 . . ? N2 C1 N1 109.2(2) . . ? N2 C1 H1 125.4 . . ? N1 C1 H1 125.4 . . ? N3 C2 N1 112.7(2) . . ? N3 C2 N4 118.2(2) . . ? N1 C2 N4 129.0(2) . . ? N5 C3 C4 111.5(2) . . ? N5 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N5 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N6 C4 C3 111.5(3) . . ? N6 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? N6 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? N7 C5 C6 110.7(3) . . ? N7 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N7 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N8 C6 C5 110.7(3) . . ? N8 C6 H6C 109.5 . . ? C5 C6 H6C 109.5 . . ? N8 C6 H6D 109.5 . . ? C5 C6 H6D 109.5 . . ? H6C C6 H6D 108.1 . . ? C8 N9 N10 104.2(3) . . ? C7 N10 N9 109.1(3) . . ? C7 N11 C8 103.8(3) . . ? N12 N12 C8 112.9(3) 3_755 . ? N10 C7 N11 110.4(3) . . ? N10 C7 H7 124.8 . . ? N11 C7 H7 124.8 . . ? N11 C8 N9 112.4(3) . . ? N11 C8 N12 127.7(3) . . ? N9 C8 N12 119.9(3) . . ? H10 O1 H11 110.5 . . ? H2 O2 H3 114.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Cd1 N1 C2 58.7(3) . . . . ? N8 Cd1 N1 C2 -119.6(3) . . . . ? N6 Cd1 N1 C2 -18.3(3) . . . . ? N7 Cd1 N1 C2 163.3(3) . . . . ? N2 Cd1 N1 C2 157.0(3) 2_645 . . . ? N5 Cd1 N1 C1 -110.8(2) . . . . ? N8 Cd1 N1 C1 70.8(2) . . . . ? N6 Cd1 N1 C1 172.2(2) . . . . ? N7 Cd1 N1 C1 -6.3(2) . . . . ? N2 Cd1 N1 C1 -12.5(5) 2_645 . . . ? C1 N2 N3 C2 0.5(3) . . . . ? Cd1 N2 N3 C2 174.36(19) 2_655 . . . ? N8 Cd1 N5 C3 -20(3) . . . . ? N6 Cd1 N5 C3 8.30(19) . . . . ? N7 Cd1 N5 C3 170.82(19) . . . . ? N1 Cd1 N5 C3 -102.22(19) . . . . ? N2 Cd1 N5 C3 90.44(19) 2_645 . . . ? N5 Cd1 N6 C4 19.51(18) . . . . ? N8 Cd1 N6 C4 -161.30(18) . . . . ? N7 Cd1 N6 C4 -79.5(4) . . . . ? N1 Cd1 N6 C4 105.67(19) . . . . ? N2 Cd1 N6 C4 -73.28(18) 2_645 . . . ? N5 Cd1 N7 C5 -166.74(18) . . . . ? N8 Cd1 N7 C5 13.59(19) . . . . ? N6 Cd1 N7 C5 -71.8(4) . . . . ? N1 Cd1 N7 C5 103.31(19) . . . . ? N2 Cd1 N7 C5 -78.08(19) 2_645 . . . ? N5 Cd1 N8 C6 -153(3) . . . . ? N6 Cd1 N8 C6 178.16(19) . . . . ? N7 Cd1 N8 C6 15.55(19) . . . . ? N1 Cd1 N8 C6 -71.46(19) . . . . ? N2 Cd1 N8 C6 95.83(19) 2_645 . . . ? N3 N2 C1 N1 -0.6(4) . . . . ? Cd1 N2 C1 N1 -174.60(19) 2_655 . . . ? C2 N1 C1 N2 0.4(3) . . . . ? Cd1 N1 C1 N2 173.66(19) . . . . ? N2 N3 C2 N1 -0.2(4) . . . . ? N2 N3 C2 N4 -179.2(3) . . . . ? C1 N1 C2 N3 -0.1(3) . . . . ? Cd1 N1 C2 N3 -170.4(2) . . . . ? C1 N1 C2 N4 178.8(3) . . . . ? Cd1 N1 C2 N4 8.5(5) . . . . ? N4 N4 C2 N3 -175.8(3) 3_666 . . . ? N4 N4 C2 N1 5.4(5) 3_666 . . . ? Cd1 N5 C3 C4 -35.1(3) . . . . ? Cd1 N6 C4 C3 -45.3(3) . . . . ? N5 C3 C4 N6 56.4(3) . . . . ? Cd1 N7 C5 C6 -40.9(3) . . . . ? Cd1 N8 C6 C5 -42.8(3) . . . . ? N7 C5 C6 N8 58.4(3) . . . . ? C8 N9 N10 C7 -0.7(4) . . . . ? N9 N10 C7 N11 0.5(4) . . . . ? C8 N11 C7 N10 0.0(4) . . . . ? C7 N11 C8 N9 -0.5(4) . . . . ? C7 N11 C8 N12 -179.6(3) . . . . ? N10 N9 C8 N11 0.7(4) . . . . ? N10 N9 C8 N12 179.9(3) . . . . ? N12 N12 C8 N11 -13.6(6) 3_755 . . . ? N12 N12 C8 N9 167.3(4) 3_755 . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.092 _refine_diff_density_min -0.815 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 897043' ####################################################################### # # 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_wn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H14 Mn N8 O6' _chemical_formula_weight 325.17 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3061(9) _cell_length_b 6.9947(10) _cell_length_c 7.9080(12) _cell_angle_alpha 76.149(5) _cell_angle_beta 74.174(5) _cell_angle_gamma 69.324(5) _cell_volume 309.99(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3711 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 25.000 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 167.0 _exptl_absorpt_coefficient_mu 1.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.621 _exptl_absorpt_correction_T_max 0.636 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4078 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1093 _reflns_number_gt 1071 _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^)+(0.0669P)^2^+0.4978P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.078(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1089 _refine_ls_number_parameters 102 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.133 _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 1.0000 0.5000 1.0000 0.0252(3) Uani 1 2 d S . . O1 O 1.1619(5) 0.6973(5) 1.0510(3) 0.0447(7) Uani 1 1 d D . . H2 H 1.2438 0.6312 1.1294 0.067 Uiso 1 1 d RD . . H3 H 1.2499 0.7365 0.9552 0.067 Uiso 1 1 d RD . . O2 O 0.6627(4) 0.7274(4) 1.0669(3) 0.0378(6) Uani 1 1 d D . . H4 H 0.5911 0.7556 0.9827 0.057 Uiso 1 1 d RD . . H5 H 0.5843 0.6787 1.1626 0.057 Uiso 1 1 d RD . . N1 N 1.0342(4) 0.6502(4) 0.7050(3) 0.0259(6) Uani 1 1 d . . . N2 N 0.8988(5) 0.8147(5) 0.4708(4) 0.0336(7) Uani 1 1 d . . . N3 N 1.1230(5) 0.7270(4) 0.4115(4) 0.0309(7) Uani 1 1 d . . . C2 C 1.2025(5) 0.6270(5) 0.5582(4) 0.0248(7) Uani 1 1 d . . . C1 C 0.8449(5) 0.7699(5) 0.6450(4) 0.0205(6) Uani 1 1 d . . . H1 H 0.6977 0.8149 0.7151 0.025 Uiso 1 1 calc R . . N4 N 1.4296(5) 0.5065(4) 0.5734(4) 0.0265(6) Uani 1 1 d . . . O3 O 0.6349(4) 1.0560(4) 1.2096(3) 0.0356(6) Uani 1 1 d D . . H7 H 0.6253 0.9642 1.1622 0.053 Uiso 1 1 d RD . . H6 H 0.6920 0.9935 1.2975 0.070(18) Uiso 1 1 d RD . . 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 0.0210(4) 0.0345(5) 0.0164(4) -0.0016(3) -0.0028(3) -0.0064(3) O1 0.0561(17) 0.0669(18) 0.0227(13) -0.0027(12) -0.0045(12) -0.0384(15) O2 0.0266(12) 0.0469(15) 0.0304(13) -0.0018(11) -0.0053(10) -0.0034(11) N1 0.0207(13) 0.0327(14) 0.0179(13) -0.0021(10) -0.0015(10) -0.0040(11) N2 0.0277(15) 0.0428(17) 0.0226(14) -0.0016(12) -0.0062(11) -0.0032(13) N3 0.0293(14) 0.0395(16) 0.0179(13) -0.0020(11) -0.0036(11) -0.0061(12) C2 0.0245(16) 0.0292(16) 0.0176(15) -0.0035(12) -0.0015(12) -0.0068(13) C1 0.0125(13) 0.0286(15) 0.0132(13) -0.0021(11) -0.0015(10) 0.0006(11) N4 0.0207(13) 0.0336(14) 0.0193(12) -0.0022(10) -0.0010(9) -0.0050(11) O3 0.0289(13) 0.0459(14) 0.0248(13) 0.0002(10) -0.0062(10) -0.0063(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.144(3) 2_767 ? Mn1 O1 2.144(3) . ? Mn1 O2 2.176(2) 2_767 ? Mn1 O2 2.176(2) . ? Mn1 N1 2.303(3) . ? Mn1 N1 2.303(3) 2_767 ? O1 H2 0.8571 . ? O1 H3 0.8575 . ? O2 H4 0.8514 . ? O2 H5 0.8515 . ? N1 C1 1.329(4) . ? N1 C2 1.340(4) . ? N2 N3 1.326(4) . ? N2 C1 1.313(4) . ? N3 C2 1.330(4) . ? C2 N4 1.403(4) . ? C1 H1 0.9300 . ? N4 N4 1.256(5) 2_866 ? O3 H7 0.8437 . ? O3 H6 0.8270 . ? 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 O1 180.000(1) 2_767 . ? O1 Mn1 O2 89.81(11) 2_767 2_767 ? O1 Mn1 O2 90.19(11) . 2_767 ? O1 Mn1 O2 90.19(11) 2_767 . ? O1 Mn1 O2 89.81(11) . . ? O2 Mn1 O2 180.000(1) 2_767 . ? O1 Mn1 N1 89.06(10) 2_767 . ? O1 Mn1 N1 90.94(10) . . ? O2 Mn1 N1 89.30(9) 2_767 . ? O2 Mn1 N1 90.70(9) . . ? O1 Mn1 N1 90.94(10) 2_767 2_767 ? O1 Mn1 N1 89.06(10) . 2_767 ? O2 Mn1 N1 90.70(9) 2_767 2_767 ? O2 Mn1 N1 89.30(9) . 2_767 ? N1 Mn1 N1 180.000(1) . 2_767 ? Mn1 O1 H2 109.5 . . ? Mn1 O1 H3 110.2 . . ? H2 O1 H3 109.0 . . ? Mn1 O2 H4 109.3 . . ? Mn1 O2 H5 109.7 . . ? H4 O2 H5 109.5 . . ? C1 N1 C2 104.4(2) . . ? C1 N1 Mn1 119.25(19) . . ? C2 N1 Mn1 135.5(2) . . ? N3 N2 C1 110.5(3) . . ? N2 N3 C2 104.0(3) . . ? N3 C2 N1 111.9(3) . . ? N3 C2 N4 128.4(3) . . ? N1 C2 N4 119.6(3) . . ? N2 C1 N1 109.1(3) . . ? N2 C1 H1 125.4 . . ? N1 C1 H1 125.4 . . ? N4 N4 C2 113.6(3) 2_866 . ? H7 O3 H6 105.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 N1 C1 70.0(2) 2_767 . . . ? O1 Mn1 N1 C1 -110.0(2) . . . . ? O2 Mn1 N1 C1 159.8(2) 2_767 . . . ? O2 Mn1 N1 C1 -20.2(2) . . . . ? N1 Mn1 N1 C1 -57(100) 2_767 . . . ? O1 Mn1 N1 C2 -98.0(3) 2_767 . . . ? O1 Mn1 N1 C2 82.0(3) . . . . ? O2 Mn1 N1 C2 -8.1(3) 2_767 . . . ? O2 Mn1 N1 C2 171.9(3) . . . . ? N1 Mn1 N1 C2 135(100) 2_767 . . . ? C1 N2 N3 C2 0.0(4) . . . . ? N2 N3 C2 N1 0.2(4) . . . . ? N2 N3 C2 N4 179.7(3) . . . . ? C1 N1 C2 N3 -0.2(4) . . . . ? Mn1 N1 C2 N3 168.9(2) . . . . ? C1 N1 C2 N4 -179.9(3) . . . . ? Mn1 N1 C2 N4 -10.7(5) . . . . ? N3 N2 C1 N1 -0.1(4) . . . . ? C2 N1 C1 N2 0.2(4) . . . . ? Mn1 N1 C1 N2 -171.1(2) . . . . ? N3 C2 N4 N4 -0.8(6) . . . 2_866 ? N1 C2 N4 N4 178.8(3) . . . 2_866 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.697 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 897044' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H22 N12 O2 Zn' _chemical_formula_weight 379.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7533(3) _cell_length_b 13.1193(5) _cell_length_c 15.5043(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.829(3) _cell_angle_gamma 90.00 _cell_volume 1553.92(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1940 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.510 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784.0 _exptl_absorpt_coefficient_mu 1.612 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.497 _exptl_absorpt_correction_T_max 0.516 _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 none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13497 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3551 _reflns_number_gt 2277 _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^)+(0.1008P)^2^+4.9512P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3531 _refine_ls_number_parameters 279 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1130 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.2221 _refine_ls_wR_factor_gt 0.1930 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _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 Zn1 Zn 0.9848(6) 0.8272(3) 0.2370(2) 0.0362(6) Uani 0.67 1 d P . . N6 N 1.2454(5) 0.8331(3) 0.2124(3) 0.0415(10) Uani 1 1 d . . . H6 H 1.3396 0.8539 0.2518 0.050 Uiso 1 1 calc R . . N8 N 0.7202(5) 0.8622(3) 0.2391(3) 0.0425(10) Uani 1 1 d . . . H8 H 0.6287 0.8448 0.1967 0.051 Uiso 1 1 calc R . . N5 N 0.9416(5) 0.7577(3) 0.1117(2) 0.0425(10) Uani 1 1 d . . . H5 H 0.8353 0.7434 0.0791 0.051 Uiso 1 1 calc R . . N7 N 1.0232(5) 0.9078(3) 0.3582(3) 0.0442(10) Uani 1 1 d . . . H7 H 1.1286 0.9186 0.3929 0.053 Uiso 1 1 calc R . . N2 N 1.0031(6) 0.6786(3) 0.3088(3) 0.0406(7) Uani 1 1 d U . . C3 C 1.1086(8) 0.7136(4) 0.0992(3) 0.0492(13) Uani 1 1 d . . . H3A H 1.1028 0.6944 0.0384 0.059 Uiso 1 1 calc R . . H3B H 1.1324 0.6528 0.1348 0.059 Uiso 1 1 calc R . . C4 C 1.2545(7) 0.7907(4) 0.1250(3) 0.0498(13) Uani 1 1 d . . . H4A H 1.3669 0.7580 0.1260 0.060 Uiso 1 1 calc R . . H4B H 1.2434 0.8453 0.0823 0.060 Uiso 1 1 calc R . . C5 C 0.8533(7) 0.9059(4) 0.3886(4) 0.0515(13) Uani 1 1 d . . . H5A H 0.8537 0.9554 0.4351 0.062 Uiso 1 1 calc R . . H5B H 0.8342 0.8389 0.4118 0.062 Uiso 1 1 calc R . . C6 C 0.7089(7) 0.9300(4) 0.3145(4) 0.0503(13) Uani 1 1 d . . . H6A H 0.5967 0.9209 0.3331 0.060 Uiso 1 1 calc R . . H6B H 0.7179 1.0006 0.2970 0.060 Uiso 1 1 calc R . . C1 C 1.0183(6) 0.5914(4) 0.2727(3) 0.0404(7) Uani 1 1 d U . . H1 H 1.0258 0.5815 0.2141 0.048 Uiso 1 1 calc R . . N1 N 0.9928(6) 0.6679(3) 0.3927(3) 0.0490(8) Uani 1 1 d U . . C2 C 1.0048(7) 0.5695(4) 0.4047(3) 0.0478(7) Uani 1 1 d DU . . N3 N 1.0215(6) 0.5181(3) 0.3314(3) 0.0453(6) Uani 1 1 d U . . N4 N 0.9882(14) 0.5462(10) 0.4928(7) 0.029(2) Uani 0.50 1 d PD . . N11 N 0.5018(7) 0.6811(3) 0.3961(3) 0.0552(13) Uani 1 1 d . . . C8 C 0.5253(6) 0.5838(3) 0.4149(3) 0.0372(11) Uani 1 1 d . . . C7 C 0.5324(7) 0.6891(4) 0.3150(3) 0.0436(8) Uani 1 1 d U . . H7A H 0.5271 0.7494 0.2831 0.052 Uiso 1 1 calc R . . N9 N 0.5673(6) 0.5308(3) 0.3485(3) 0.0454(10) Uani 1 1 d . . . N10 N 0.5714(6) 0.5997(3) 0.2863(3) 0.0454(8) Uani 1 1 d U . . N12 N 0.5033(6) 0.5471(3) 0.4983(3) 0.0463(11) Uani 1 1 d . . . O1 O 0.3991(5) 0.8720(3) 0.4642(3) 0.0576(10) Uani 1 1 d D . . O2 O 0.6485(6) 0.5718(3) 0.1106(3) 0.0588(11) Uani 1 1 d D . . Zn2 Zn 0.9875(14) 0.8534(6) 0.2266(6) 0.061(2) Uani 0.33 1 d P . . N13 N 0.9804(16) 0.5234(14) 0.5314(9) 0.049(3) Uani 0.50 1 d P . . H2A H 0.634(9) 0.578(4) 0.1629(16) 0.073 Uiso 1 1 d D . . H2B H 0.629(9) 0.5116(19) 0.092(3) 0.073 Uiso 1 1 d D . . H2 H 0.471(6) 0.886(4) 0.508(3) 0.073 Uiso 1 1 d D . . H3 H 0.430(8) 0.820(3) 0.444(4) 0.073 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0346(7) 0.0431(16) 0.0317(6) -0.0047(8) 0.0075(5) -0.0025(10) N6 0.033(2) 0.041(2) 0.050(3) -0.0018(19) 0.0059(18) 0.0009(17) N8 0.034(2) 0.036(2) 0.056(3) -0.0051(19) 0.0030(18) -0.0022(17) N5 0.044(2) 0.052(2) 0.032(2) -0.0047(19) 0.0056(17) -0.0086(19) N7 0.038(2) 0.048(2) 0.046(3) 0.000(2) 0.0072(18) 0.0015(18) N2 0.0496(15) 0.0414(14) 0.0316(14) 0.0078(12) 0.0091(12) -0.0005(13) C3 0.069(4) 0.041(3) 0.042(3) 0.000(2) 0.020(3) 0.002(3) C4 0.050(3) 0.058(3) 0.044(3) 0.004(3) 0.015(2) 0.005(3) C5 0.057(3) 0.054(3) 0.047(3) 0.001(3) 0.017(3) 0.006(3) C6 0.041(3) 0.046(3) 0.066(4) -0.007(3) 0.017(3) 0.003(2) C1 0.0489(14) 0.0416(13) 0.0317(13) 0.0086(11) 0.0102(11) -0.0007(12) N1 0.0537(16) 0.0554(16) 0.0375(15) 0.0064(14) 0.0071(13) -0.0043(14) C2 0.0520(14) 0.0533(14) 0.0379(13) 0.0095(12) 0.0068(12) -0.0044(13) N3 0.0510(14) 0.0474(13) 0.0374(13) 0.0100(11) 0.0077(11) -0.0024(12) N4 0.039(4) 0.032(7) 0.018(5) 0.007(4) 0.009(4) -0.001(4) N11 0.077(3) 0.029(2) 0.062(3) 0.007(2) 0.020(3) 0.002(2) C8 0.043(3) 0.027(2) 0.043(3) 0.003(2) 0.011(2) -0.0006(19) C7 0.056(2) 0.0369(17) 0.0381(19) 0.0066(16) 0.0097(16) -0.0051(16) N9 0.061(3) 0.036(2) 0.040(2) -0.0042(18) 0.010(2) -0.0026(19) N10 0.057(2) 0.0404(17) 0.0388(18) 0.0049(15) 0.0092(15) -0.0050(16) N12 0.064(3) 0.035(2) 0.043(2) 0.002(2) 0.017(2) 0.005(2) O1 0.060(3) 0.050(2) 0.063(3) -0.001(2) 0.012(2) 0.005(2) O2 0.073(3) 0.057(2) 0.050(2) -0.0030(19) 0.018(2) -0.011(2) Zn2 0.0371(16) 0.056(4) 0.090(5) -0.037(3) 0.013(3) -0.006(3) N13 0.050(6) 0.051(9) 0.050(8) -0.016(8) 0.019(6) 0.000(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N8 2.108(6) . ? Zn1 N5 2.120(6) . ? Zn1 N6 2.120(6) . ? Zn1 N7 2.133(6) . ? Zn1 N2 2.238(5) . ? N6 C4 1.477(6) . ? N6 Zn2 2.066(11) . ? N6 H6 0.9100 . ? N8 C6 1.483(7) . ? N8 Zn2 2.117(11) . ? N8 H8 0.9100 . ? N5 C3 1.460(7) . ? N5 Zn2 2.159(10) . ? N5 H5 0.9100 . ? N7 C5 1.473(6) . ? N7 Zn2 2.134(10) . ? N7 H7 0.9100 . ? N2 C1 1.288(6) . ? N2 N1 1.324(5) . ? C3 C4 1.519(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.495(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C1 N3 1.321(6) . ? C1 H1 0.9300 . ? N1 C2 1.306(6) . ? C2 N3 1.347(7) . ? C2 N4 1.428(11) . ? C2 N13 1.56(2) 3_766 ? N3 Zn2 2.336(8) 2_745 ? N4 N13 0.681(11) . ? N4 N13 1.032(9) 3_766 ? N4 N4 1.24(3) 3_766 ? N11 C8 1.315(6) . ? N11 C7 1.322(6) . ? C8 N9 1.328(6) . ? C8 N12 1.417(6) . ? C7 N10 1.309(6) . ? C7 H7A 0.9300 . ? N9 N10 1.326(6) . ? N12 N12 1.240(8) 3_666 ? O1 H2 0.82(2) . ? O1 H3 0.807(19) . ? O2 H2A 0.842(10) . ? O2 H2B 0.844(10) . ? Zn2 N3 2.336(8) 2_755 ? N13 N4 1.032(9) 3_766 ? N13 N13 1.23(2) 3_766 ? N13 C2 1.56(2) 3_766 ? 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 N8 Zn1 N5 96.1(2) . . ? N8 Zn1 N6 162.6(2) . . ? N5 Zn1 N6 81.8(2) . . ? N8 Zn1 N7 82.4(2) . . ? N5 Zn1 N7 175.7(2) . . ? N6 Zn1 N7 98.4(2) . . ? N8 Zn1 N2 99.3(2) . . ? N5 Zn1 N2 93.9(2) . . ? N6 Zn1 N2 98.1(2) . . ? N7 Zn1 N2 90.37(19) . . ? C4 N6 Zn2 110.2(4) . . ? C4 N6 Zn1 110.3(3) . . ? Zn2 N6 Zn1 10.4(3) . . ? C4 N6 H6 124.8 . . ? Zn2 N6 H6 124.8 . . ? Zn1 N6 H6 124.8 . . ? C6 N8 Zn1 109.4(3) . . ? C6 N8 Zn2 107.2(4) . . ? Zn1 N8 Zn2 10.4(3) . . ? C6 N8 H8 125.1 . . ? Zn1 N8 H8 125.1 . . ? Zn2 N8 H8 125.1 . . ? C3 N5 Zn1 106.6(3) . . ? C3 N5 Zn2 108.3(4) . . ? Zn1 N5 Zn2 10.2(2) . . ? C3 N5 H5 125.8 . . ? Zn1 N5 H5 125.8 . . ? Zn2 N5 H5 125.8 . . ? C5 N7 Zn1 106.0(3) . . ? C5 N7 Zn2 108.9(4) . . ? Zn1 N7 Zn2 10.3(2) . . ? C5 N7 H7 125.1 . . ? Zn1 N7 H7 125.1 . . ? Zn2 N7 H7 125.1 . . ? C1 N2 N1 111.0(4) . . ? C1 N2 Zn1 124.1(3) . . ? N1 N2 Zn1 124.8(3) . . ? N5 C3 C4 109.8(4) . . ? N5 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? N5 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N6 C4 C3 110.0(4) . . ? N6 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N6 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N7 C5 C6 110.1(4) . . ? N7 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? N7 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.2 . . ? N8 C6 C5 109.9(4) . . ? N8 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N8 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N2 C1 N3 109.9(4) . . ? N2 C1 H1 125.1 . . ? N3 C1 H1 125.1 . . ? C2 N1 N2 103.2(4) . . ? N1 C2 N3 113.0(4) . . ? N1 C2 N4 109.4(7) . . ? N3 C2 N4 137.6(7) . . ? N1 C2 N13 149.0(7) . 3_766 ? N3 C2 N13 97.9(6) . 3_766 ? N4 C2 N13 40.1(4) . 3_766 ? C1 N3 C2 102.9(4) . . ? C1 N3 Zn2 114.4(4) . 2_745 ? C2 N3 Zn2 141.9(4) . 2_745 ? N13 N4 N13 90(2) . 3_766 ? N13 N4 N4 56.3(17) . 3_766 ? N13 N4 N4 33.3(8) 3_766 3_766 ? N13 N4 C2 166(3) . . ? N13 N4 C2 77.0(16) 3_766 . ? N4 N4 C2 110.3(17) 3_766 . ? C8 N11 C7 104.4(4) . . ? N11 C8 N9 112.2(4) . . ? N11 C8 N12 119.9(4) . . ? N9 C8 N12 127.9(4) . . ? N10 C7 N11 110.0(4) . . ? N10 C7 H7A 125.0 . . ? N11 C7 H7A 125.0 . . ? N10 N9 C8 104.3(4) . . ? C7 N10 N9 109.1(4) . . ? N12 N12 C8 112.9(5) 3_666 . ? H2 O1 H3 108(3) . . ? H2A O2 H2B 112(3) . . ? N6 Zn2 N8 175.6(5) . . ? N6 Zn2 N7 100.1(5) . . ? N8 Zn2 N7 82.1(4) . . ? N6 Zn2 N5 82.1(4) . . ? N8 Zn2 N5 94.7(4) . . ? N7 Zn2 N5 163.6(4) . . ? N6 Zn2 N3 92.5(3) . 2_755 ? N8 Zn2 N3 91.1(4) . 2_755 ? N7 Zn2 N3 92.8(4) . 2_755 ? N5 Zn2 N3 103.4(4) . 2_755 ? N4 N13 N4 90(2) . 3_766 ? N4 N13 N13 56.8(16) . 3_766 ? N4 N13 N13 33.5(9) 3_766 3_766 ? N4 N13 C2 153(3) . 3_766 ? N4 N13 C2 62.9(13) 3_766 3_766 ? N13 N13 C2 96(2) 3_766 3_766 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.302 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 897045' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H34 Co N20 O6 ' _chemical_formula_weight 613.52 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.8920(3) _cell_length_b 7.2477(2) _cell_length_c 14.5382(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.479(2) _cell_angle_gamma 90.00 _cell_volume 1239.35(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5784 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 27.530 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.392 _exptl_crystal_size_mid 0.244 _exptl_crystal_size_min 0.198 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 642.0 _exptl_absorpt_coefficient_mu 0.768 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.859 _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 none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 9976 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2858 _reflns_number_gt 2279 _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^)+(0.1208P)^2^+3.1866P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2848 _refine_ls_number_parameters 220 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.2087 _refine_ls_wR_factor_gt 0.1980 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.71401(10) 0.7500 0.0186(3) Uani 1 2 d SD . . N1 N 0.6747(3) 0.7184(5) 0.7252(2) 0.0266(7) Uani 1 1 d . . . N10 N 0.4596(3) 0.9019(5) 0.6408(2) 0.0279(7) Uani 1 1 d D . . N9 N 0.4597(3) 0.5181(5) 0.6442(2) 0.0289(8) Uani 1 1 d D . . N2 N 0.7680(3) 0.7450(5) 0.7861(2) 0.0272(8) Uani 1 1 d . . . N3 N 0.8145(3) 0.6945(6) 0.6464(3) 0.0346(9) Uani 1 1 d . . . C1 C 0.7021(3) 0.6868(6) 0.6422(3) 0.0265(9) Uani 1 1 d . . . H1 H 0.6508 0.6627 0.5888 0.032 Uiso 1 1 calc R . . C2 C 0.8521(3) 0.7292(6) 0.7350(3) 0.0247(8) Uani 1 1 d . . . N4 N 0.9653(3) 0.7390(5) 0.7783(3) 0.0278(7) Uani 1 1 d . . . C6 C 0.4459(4) 0.8010(7) 0.5516(3) 0.0331(10) Uani 1 1 d D . . C5 C 0.3951(4) 0.6128(7) 0.5630(3) 0.0330(9) Uani 1 1 d D . . N7 N 0.8065(3) 0.2242(5) 0.7987(3) 0.0324(8) Uani 1 1 d . . . H7 H 0.8414 0.2375 0.8545 0.039 Uiso 1 1 calc R . . C4 C 0.8518(4) 0.2040(6) 0.7220(3) 0.0294(9) Uani 1 1 d . . . N5 N 0.6751(3) 0.1955(6) 0.6794(3) 0.0407(10) Uani 1 1 d . . . N6 N 0.7732(3) 0.1873(6) 0.6472(3) 0.0372(9) Uani 1 1 d . . . C3 C 0.6937(3) 0.2196(6) 0.7706(3) 0.0278(9) Uani 1 1 d . . . H3 H 0.6380 0.2314 0.8088 0.033 Uiso 1 1 calc R . . N8 N 0.9668(3) 0.2011(5) 0.7120(3) 0.0320(8) Uani 1 1 d . . . O1 O 0.8526(3) 0.0977(5) 0.4758(2) 0.0384(8) Uani 1 1 d D . . O2 O 0.9306(4) 0.2680(5) 0.9842(3) 0.0442(9) Uani 1 1 d D . . H6 H 0.318(2) 0.617(9) 0.573(4) 0.053 Uiso 1 1 d D . . H5 H 0.392(5) 0.542(7) 0.507(3) 0.053 Uiso 1 1 d D . . H8 H 0.521(3) 0.794(8) 0.532(4) 0.053 Uiso 1 1 d D . . H9 H 0.394(4) 0.868(8) 0.506(3) 0.053 Uiso 1 1 d D . . H10 H 0.518(4) 0.985(7) 0.642(4) 0.053 Uiso 1 1 d D . . H11 H 0.391(3) 0.955(8) 0.639(4) 0.053 Uiso 1 1 d D . . H12 H 0.814(4) 0.111(10) 0.516(3) 0.066 Uiso 1 1 d D . . H13 H 0.820(5) 0.126(10) 0.426(2) 0.066 Uiso 1 1 d D . . O3 O 0.9602(5) 0.4578(7) 0.9614(3) 0.0753(14) Uani 1 1 d D . . H15 H 0.959(8) 0.163(6) 0.975(5) 0.113 Uiso 1 1 d D . . H14 H 0.904(8) 0.251(11) 1.034(4) 0.113 Uiso 1 1 d D . . H16 H 0.992(6) 0.446(14) 0.911(4) 0.113 Uiso 1 1 d D . . H17 H 0.899(5) 0.516(12) 0.936(5) 0.113 Uiso 1 1 d D . . H2 H 0.482(4) 0.416(6) 0.680(3) 0.090 Uiso 1 1 d D . . H4 H 0.522(2) 0.527(3) 0.619(2) 0.090 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 0.0126(4) 0.0282(4) 0.0152(4) 0.000 0.0024(2) 0.000 N1 0.0166(16) 0.0386(19) 0.0250(17) -0.0020(14) 0.0041(13) -0.0013(13) N10 0.0224(16) 0.0353(19) 0.0259(17) 0.0015(14) 0.0036(13) 0.0002(14) N9 0.0238(17) 0.0349(19) 0.0279(18) -0.0022(14) 0.0038(13) -0.0014(14) N2 0.0175(16) 0.043(2) 0.0219(17) -0.0020(14) 0.0046(13) -0.0015(14) N3 0.0176(17) 0.061(3) 0.0256(18) -0.0076(17) 0.0049(13) -0.0005(16) C1 0.0083(16) 0.055(3) 0.0164(17) -0.0060(16) 0.0018(13) 0.0000(15) C2 0.0178(18) 0.034(2) 0.0223(19) 0.0022(15) 0.0024(15) -0.0009(15) N4 0.0172(16) 0.0401(19) 0.0267(17) -0.0001(14) 0.0056(13) -0.0001(14) C6 0.030(2) 0.051(3) 0.0186(19) 0.0034(17) 0.0038(16) 0.0025(19) C5 0.027(2) 0.046(3) 0.026(2) -0.0066(18) 0.0033(16) -0.0012(18) N7 0.0271(18) 0.047(2) 0.0220(18) -0.0041(15) 0.0014(14) -0.0032(16) C4 0.026(2) 0.035(2) 0.028(2) 0.0001(16) 0.0061(16) -0.0004(16) N5 0.027(2) 0.060(3) 0.034(2) -0.0046(18) -0.0008(16) 0.0001(17) N6 0.0267(19) 0.059(3) 0.0252(18) -0.0020(17) 0.0011(15) -0.0002(17) C3 0.0167(18) 0.044(2) 0.0233(19) -0.0019(17) 0.0055(14) -0.0006(16) N8 0.0234(17) 0.046(2) 0.0269(18) 0.0005(15) 0.0028(14) -0.0009(15) O1 0.0379(18) 0.0429(18) 0.0346(17) 0.0012(15) 0.0066(14) 0.0054(14) O2 0.048(2) 0.046(2) 0.040(2) -0.0020(15) 0.0101(17) -0.0071(16) O3 0.087(4) 0.060(3) 0.073(3) -0.001(2) -0.007(3) -0.010(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 N10 2.093(4) 2_656 ? Co1 N10 2.093(4) . ? Co1 N9 2.096(4) . ? Co1 N9 2.096(4) 2_656 ? Co1 N1 2.160(3) 2_656 ? Co1 N1 2.160(3) . ? N1 C1 1.315(5) . ? N1 N2 1.328(5) . ? N10 C6 1.477(6) . ? N10 H10 0.91(2) . ? N10 H11 0.90(2) . ? N9 C5 1.478(6) . ? N9 H2 0.924(16) . ? N9 H4 0.87(2) . ? N2 C2 1.336(5) . ? N3 C2 1.323(5) . ? N3 C1 1.331(5) . ? C1 H1 0.9300 . ? C2 N4 1.402(5) . ? N4 N4 1.248(7) 2_756 ? C6 C5 1.510(7) . ? C6 H8 0.97(2) . ? C6 H9 0.96(2) . ? C5 H6 0.95(2) . ? C5 H5 0.96(2) . ? N7 C4 1.316(6) . ? N7 C3 1.344(5) . ? N7 H7 0.8600 . ? C4 N6 1.331(6) . ? C4 N8 1.396(6) . ? N5 N6 1.320(6) . ? N5 C3 1.322(6) . ? C3 H3 0.9300 . ? N8 N8 1.260(7) 2_756 ? O1 H12 0.802(19) . ? O1 H13 0.79(2) . ? O2 H15 0.85(2) . ? O2 H14 0.85(2) . ? O3 O3 1.488(10) 3_767 ? O3 H16 0.88(2) . ? O3 H17 0.88(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N10 Co1 N10 98.8(2) 2_656 . ? N10 Co1 N9 177.93(14) 2_656 . ? N10 Co1 N9 83.22(14) . . ? N10 Co1 N9 83.22(14) 2_656 2_656 ? N10 Co1 N9 177.93(14) . 2_656 ? N9 Co1 N9 94.7(2) . 2_656 ? N10 Co1 N1 89.01(13) 2_656 2_656 ? N10 Co1 N1 89.90(13) . 2_656 ? N9 Co1 N1 90.63(14) . 2_656 ? N9 Co1 N1 90.50(13) 2_656 2_656 ? N10 Co1 N1 89.90(13) 2_656 . ? N10 Co1 N1 89.01(13) . . ? N9 Co1 N1 90.50(13) . . ? N9 Co1 N1 90.63(13) 2_656 . ? N1 Co1 N1 178.3(2) 2_656 . ? C1 N1 N2 109.9(3) . . ? C1 N1 Co1 121.7(3) . . ? N2 N1 Co1 128.4(3) . . ? C6 N10 Co1 109.1(3) . . ? C6 N10 H10 109(4) . . ? Co1 N10 H10 109(4) . . ? C6 N10 H11 102(4) . . ? Co1 N10 H11 114(4) . . ? H10 N10 H11 114(6) . . ? C5 N9 Co1 107.9(3) . . ? C5 N9 H2 154(4) . . ? Co1 N9 H2 96(4) . . ? C5 N9 H4 90(2) . . ? Co1 N9 H4 98.1(17) . . ? H2 N9 H4 96(2) . . ? N1 N2 C2 103.7(3) . . ? C2 N3 C1 104.2(3) . . ? N1 C1 N3 109.5(3) . . ? N1 C1 H1 125.3 . . ? N3 C1 H1 125.3 . . ? N3 C2 N2 112.6(4) . . ? N3 C2 N4 127.7(4) . . ? N2 C2 N4 119.6(4) . . ? N4 N4 C2 112.8(5) 2_756 . ? N10 C6 C5 110.2(3) . . ? N10 C6 H8 107(4) . . ? C5 C6 H8 113(3) . . ? N10 C6 H9 109(4) . . ? C5 C6 H9 108(4) . . ? H8 C6 H9 110(5) . . ? N9 C5 C6 109.8(3) . . ? N9 C5 H6 107(4) . . ? C6 C5 H6 113(4) . . ? N9 C5 H5 112(4) . . ? C6 C5 H5 111(4) . . ? H6 C5 H5 103(5) . . ? C4 N7 C3 104.7(4) . . ? C4 N7 H7 127.6 . . ? C3 N7 H7 127.6 . . ? N7 C4 N6 112.1(4) . . ? N7 C4 N8 128.3(4) . . ? N6 C4 N8 119.6(4) . . ? N6 N5 C3 109.6(4) . . ? N5 N6 C4 104.9(4) . . ? N5 C3 N7 108.7(4) . . ? N5 C3 H3 125.7 . . ? N7 C3 H3 125.7 . . ? N8 N8 C4 114.0(5) 2_756 . ? H12 O1 H13 112(4) . . ? H15 O2 H14 102(3) . . ? O3 O3 H16 111(6) 3_767 . ? O3 O3 H17 121(6) 3_767 . ? H16 O3 H17 97(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.779 _refine_diff_density_min -1.152 _refine_diff_density_rms 0.128 _database_code_depnum_ccdc_archive 'CCDC 920311' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 Cu N12' _chemical_formula_weight 345.89 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0262(4) _cell_length_b 8.4500(5) _cell_length_c 12.2755(9) _cell_angle_alpha 103.213(4) _cell_angle_beta 97.971(4) _cell_angle_gamma 105.300(3) _cell_volume 668.83(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3085 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 27.530 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 1.650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.714 _exptl_absorpt_correction_T_max 0.743 _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 none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10528 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.59 _reflns_number_total 3085 _reflns_number_gt 2663 _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^)+(0.0684P)^2^+0.4811P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3035 _refine_ls_number_parameters 251 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.052 _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 Cu1 Cu 0.0000 0.0000 0.0000 0.02784(14) Uani 1 2 d S . . Cu2 Cu 0.0000 -0.5000 -0.5000 0.02743(14) Uani 1 2 d S . . C7 C 0.5382(3) 0.5916(3) 0.14764(19) 0.0293(4) Uani 1 1 d . . . N10 N 0.4698(3) 0.4691(3) 0.19662(16) 0.0342(4) Uani 1 1 d . . . N12 N 0.6188(3) 0.7452(3) 0.22291(18) 0.0392(5) Uani 1 1 d . . . C8 C 0.6003(4) 0.7149(3) 0.32310(18) 0.0323(5) Uani 1 1 d . . . H8 H 0.6437 0.7972 0.3936 0.039 Uiso 1 1 calc R . . N11 N 0.5112(3) 0.5506(3) 0.30773(17) 0.0399(5) Uani 1 1 d . . . N13 N 0.5354(3) 0.5756(3) 0.03096(16) 0.0326(4) Uani 1 1 d . . . N2 N 0.0353(3) -0.4315(3) -0.29023(17) 0.0365(5) Uani 1 1 d . . . C1 C 0.0252(4) -0.4292(4) -0.1215(2) 0.0434(6) Uani 1 1 d . . . C2 C 0.0639(4) -0.2741(3) -0.23099(18) 0.0298(5) Uani 1 1 d . . . H2 H 0.0848 -0.1804 -0.2605 0.036 Uiso 1 1 calc R . . N1 N 0.0092(4) -0.5332(3) -0.2226(2) 0.0446(5) Uani 1 1 d . . . N3 N 0.0588(4) -0.2682(3) -0.12278(18) 0.0455(6) Uani 1 1 d . . . N7 N 0.2987(3) -0.3865(3) -0.48159(18) 0.0325(4) Uani 1 1 d D . . N6 N 0.0214(3) -0.7378(3) -0.51010(18) 0.0346(4) Uani 1 1 d D . . N8 N 0.0209(3) -0.0820(3) 0.14281(17) 0.0312(4) Uani 1 1 d D . . N9 N 0.2999(3) 0.0987(3) 0.04971(18) 0.0325(4) Uani 1 1 d D . . C5 C 0.2285(4) -0.0042(4) 0.2108(2) 0.0415(6) Uani 1 1 d D . . C6 C 0.3693(4) 0.0094(4) 0.1285(2) 0.0392(5) Uani 1 1 d D . . C3 C -0.1668(5) -0.8403(3) -0.4889(2) 0.0445(6) Uani 1 1 d D . . C4 C 0.3390(4) -0.2011(4) -0.4496(2) 0.0447(6) Uani 1 1 d D . . N4 N 0.0171(6) -0.4245(5) -0.0031(5) 0.0278(8) Uani 0.50 1 d PU . . N5 N 0.0053(7) -0.4545(7) 0.0484(4) 0.0321(9) Uani 0.50 1 d PU . . H1 H 0.129(3) -0.734(4) -0.459(2) 0.039 Uiso 1 1 d D . . H3 H 0.037(5) -0.781(4) -0.5809(18) 0.039 Uiso 1 1 d D . . H10 H 0.335(5) -0.416(4) -0.5468(19) 0.039 Uiso 1 1 d D . . H9 H 0.366(4) -0.413(4) -0.426(2) 0.039 Uiso 1 1 d D . . H4 H -0.169(4) -0.809(4) -0.4094(16) 0.039 Uiso 1 1 d D . . H5 H -0.183(4) -0.958(2) -0.513(2) 0.039 Uiso 1 1 d D . . H7 H 0.463(3) -0.146(4) -0.466(2) 0.039 Uiso 1 1 d D . . H6 H 0.348(4) -0.163(4) -0.3699(16) 0.039 Uiso 1 1 d D . . H11 H -0.062(4) -0.059(4) 0.187(2) 0.039 Uiso 1 1 d D . . H12 H -0.009(4) -0.196(2) 0.118(2) 0.039 Uiso 1 1 d D . . H13 H 0.235(4) 0.110(3) 0.254(2) 0.039 Uiso 1 1 d D . . H14 H 0.255(4) -0.078(3) 0.257(2) 0.039 Uiso 1 1 d D . . H16 H 0.356(4) -0.104(3) 0.083(2) 0.039 Uiso 1 1 d D . . H15 H 0.508(3) 0.059(4) 0.172(2) 0.039 Uiso 1 1 d D . . H17 H 0.341(5) 0.078(4) -0.0142(19) 0.039 Uiso 1 1 d D . . H18 H 0.338(4) 0.207(2) 0.085(2) 0.039 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 Cu1 0.0268(2) 0.0284(2) 0.0279(2) 0.01238(15) 0.00609(15) 0.00361(15) Cu2 0.0273(2) 0.0235(2) 0.0335(2) 0.01167(15) 0.00757(15) 0.00719(15) C7 0.0296(11) 0.0321(11) 0.0275(10) 0.0121(8) 0.0071(8) 0.0080(9) N10 0.0378(11) 0.0358(11) 0.0273(9) 0.0131(8) 0.0073(8) 0.0045(8) N12 0.0457(12) 0.0341(11) 0.0346(10) 0.0086(8) 0.0089(9) 0.0076(9) C8 0.0358(12) 0.0350(12) 0.0213(9) 0.0024(8) 0.0052(8) 0.0081(9) N11 0.0410(11) 0.0530(13) 0.0268(9) 0.0149(9) 0.0085(8) 0.0122(10) N13 0.0371(10) 0.0338(10) 0.0284(9) 0.0136(7) 0.0090(8) 0.0082(8) N2 0.0474(12) 0.0369(11) 0.0268(9) 0.0074(8) 0.0096(8) 0.0160(9) C1 0.0346(13) 0.0678(18) 0.0370(13) 0.0318(13) 0.0093(10) 0.0152(12) C2 0.0470(13) 0.0218(10) 0.0247(9) 0.0092(8) 0.0135(9) 0.0120(9) N1 0.0467(13) 0.0336(11) 0.0593(14) 0.0215(10) 0.0112(11) 0.0148(10) N3 0.0540(14) 0.0494(14) 0.0267(10) 0.0017(9) 0.0113(9) 0.0113(11) N7 0.0304(10) 0.0407(11) 0.0280(9) 0.0138(8) 0.0081(8) 0.0090(8) N6 0.0421(11) 0.0295(10) 0.0318(10) 0.0087(8) 0.0033(9) 0.0127(9) N8 0.0355(10) 0.0299(10) 0.0304(9) 0.0115(8) 0.0114(8) 0.0087(8) N9 0.0305(10) 0.0310(10) 0.0338(10) 0.0097(8) 0.0090(8) 0.0039(8) C5 0.0431(14) 0.0534(16) 0.0276(11) 0.0143(11) 0.0050(10) 0.0128(12) C6 0.0318(12) 0.0471(15) 0.0388(13) 0.0137(11) 0.0057(10) 0.0119(11) C3 0.0600(17) 0.0254(12) 0.0460(14) 0.0137(11) 0.0116(13) 0.0062(11) C4 0.0396(14) 0.0395(14) 0.0429(14) 0.0075(11) 0.0083(11) -0.0045(11) N4 0.040(2) 0.022(3) 0.023(2) 0.007(2) 0.0085(17) 0.0095(15) N5 0.038(2) 0.032(3) 0.027(2) 0.011(3) 0.0080(18) 0.0106(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N9 1.998(2) 2 ? Cu1 N9 1.998(2) . ? Cu1 N8 2.0281(19) 2 ? Cu1 N8 2.0281(19) . ? Cu2 N7 2.021(2) . ? Cu2 N7 2.021(2) 2_544 ? Cu2 N6 2.031(2) 2_544 ? Cu2 N6 2.031(2) . ? Cu2 N2 2.468(2) 2_544 ? Cu2 N2 2.468(2) . ? C7 N10 1.329(3) . ? C7 N12 1.333(3) . ? C7 N13 1.404(3) . ? N10 N11 1.332(3) . ? N12 C8 1.329(3) . ? C8 N11 1.320(3) . ? C8 H8 0.9300 . ? N13 N13 1.254(4) 2_665 ? N2 C2 1.309(3) . ? N2 N1 1.321(3) . ? C1 N1 1.317(4) . ? C1 N3 1.323(4) . ? C1 N4 1.454(6) . ? C1 N5 1.470(7) 2_545 ? C2 N3 1.324(3) . ? C2 H2 0.9300 . ? N7 C4 1.464(4) . ? N7 H10 0.877(17) . ? N7 H9 0.887(18) . ? N6 C3 1.470(4) . ? N6 H1 0.901(18) . ? N6 H3 0.896(18) . ? N8 C5 1.470(3) . ? N8 H11 0.882(17) . ? N8 H12 0.895(18) . ? N9 C6 1.463(3) . ? N9 H17 0.869(18) . ? N9 H18 0.870(18) . ? C5 C6 1.511(4) . ? C5 H13 0.977(17) . ? C5 H14 0.966(17) . ? C6 H16 0.968(17) . ? C6 H15 0.975(17) . ? C3 C4 1.500(4) 2_544 ? C3 H4 0.955(17) . ? C3 H5 0.942(17) . ? C4 C3 1.500(4) 2_544 ? C4 H7 0.947(17) . ? C4 H6 0.944(17) . ? N4 N5 0.739(5) . ? N4 N5 1.005(5) 2_545 ? N4 N4 1.256(9) 2_545 ? N5 N4 1.005(5) 2_545 ? N5 N5 1.239(9) 2_545 ? N5 C1 1.470(7) 2_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N9 Cu1 N9 180.00(5) 2 . ? N9 Cu1 N8 84.45(8) 2 2 ? N9 Cu1 N8 95.55(8) . 2 ? N9 Cu1 N8 95.55(8) 2 . ? N9 Cu1 N8 84.45(8) . . ? N8 Cu1 N8 180.00(10) 2 . ? N7 Cu2 N7 180.00(12) . 2_544 ? N7 Cu2 N6 84.38(9) . 2_544 ? N7 Cu2 N6 95.62(9) 2_544 2_544 ? N7 Cu2 N6 95.62(9) . . ? N7 Cu2 N6 84.38(9) 2_544 . ? N6 Cu2 N6 180.000(1) 2_544 . ? N7 Cu2 N2 89.10(8) . 2_544 ? N7 Cu2 N2 90.90(8) 2_544 2_544 ? N6 Cu2 N2 92.14(8) 2_544 2_544 ? N6 Cu2 N2 87.86(8) . 2_544 ? N7 Cu2 N2 90.90(8) . . ? N7 Cu2 N2 89.10(8) 2_544 . ? N6 Cu2 N2 87.86(8) 2_544 . ? N6 Cu2 N2 92.14(8) . . ? N2 Cu2 N2 180.0 2_544 . ? N10 C7 N12 112.8(2) . . ? N10 C7 N13 127.9(2) . . ? N12 C7 N13 119.3(2) . . ? C7 N10 N11 104.00(19) . . ? C8 N12 C7 103.8(2) . . ? N11 C8 N12 109.9(2) . . ? N11 C8 H8 125.0 . . ? N12 C8 H8 125.0 . . ? C8 N11 N10 109.49(19) . . ? N13 N13 C7 113.6(2) 2_665 . ? C2 N2 N1 109.6(2) . . ? C2 N2 Cu2 119.64(15) . . ? N1 N2 Cu2 130.36(17) . . ? N1 C1 N3 113.1(2) . . ? N1 C1 N4 142.9(3) . . ? N3 C1 N4 104.0(3) . . ? N1 C1 N5 102.7(3) . 2_545 ? N3 C1 N5 144.2(3) . 2_545 ? N4 C1 N5 40.2(2) . 2_545 ? N2 C2 N3 109.9(2) . . ? N2 C2 H2 125.1 . . ? N3 C2 H2 125.1 . . ? C1 N1 N2 103.9(2) . . ? C1 N3 C2 103.5(2) . . ? C4 N7 Cu2 108.85(17) . . ? C4 N7 H10 108(2) . . ? Cu2 N7 H10 110(2) . . ? C4 N7 H9 108(2) . . ? Cu2 N7 H9 109(2) . . ? H10 N7 H9 113(3) . . ? C3 N6 Cu2 107.72(16) . . ? C3 N6 H1 110.5(19) . . ? Cu2 N6 H1 111.3(19) . . ? C3 N6 H3 111(2) . . ? Cu2 N6 H3 107(2) . . ? H1 N6 H3 109(3) . . ? C5 N8 Cu1 108.78(15) . . ? C5 N8 H11 108(2) . . ? Cu1 N8 H11 115(2) . . ? C5 N8 H12 111.2(19) . . ? Cu1 N8 H12 105.7(19) . . ? H11 N8 H12 108(3) . . ? C6 N9 Cu1 107.89(15) . . ? C6 N9 H17 112(2) . . ? Cu1 N9 H17 103(2) . . ? C6 N9 H18 109(2) . . ? Cu1 N9 H18 112(2) . . ? H17 N9 H18 112(3) . . ? N8 C5 C6 107.8(2) . . ? N8 C5 H13 105.6(18) . . ? C6 C5 H13 109.7(18) . . ? N8 C5 H14 108.1(18) . . ? C6 C5 H14 110.5(18) . . ? H13 C5 H14 115(2) . . ? N9 C6 C5 107.5(2) . . ? N9 C6 H16 107.0(18) . . ? C5 C6 H16 108.9(18) . . ? N9 C6 H15 117.1(19) . . ? C5 C6 H15 108.9(18) . . ? H16 C6 H15 107(2) . . ? N6 C3 C4 108.0(2) . 2_544 ? N6 C3 H4 110.5(18) . . ? C4 C3 H4 106.5(19) 2_544 . ? N6 C3 H5 111.7(19) . . ? C4 C3 H5 110.7(19) 2_544 . ? H4 C3 H5 109(3) . . ? N7 C4 C3 109.1(2) . 2_544 ? N7 C4 H7 110.6(18) . . ? C3 C4 H7 111.6(19) 2_544 . ? N7 C4 H6 108.1(19) . . ? C3 C4 H6 109.0(19) 2_544 . ? H7 C4 H6 108(3) . . ? N5 N4 N5 89.2(7) . 2_545 ? N5 N4 N4 53.1(5) . 2_545 ? N5 N4 N4 36.0(3) 2_545 2_545 ? N5 N4 C1 159.9(8) . . ? N5 N4 C1 70.8(6) 2_545 . ? N4 N4 C1 106.8(6) 2_545 . ? N4 N5 N4 90.8(7) . 2_545 ? N4 N5 N5 54.2(5) . 2_545 ? N4 N5 N5 36.6(3) 2_545 2_545 ? N4 N5 C1 159.9(8) . 2_545 ? N4 N5 C1 69.1(6) 2_545 2_545 ? N5 N5 C1 105.7(7) 2_545 2_545 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.778 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 920312' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H48 Mn2 N24 O6' _chemical_formula_weight 1166.98 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.8748(3) _cell_length_b 25.0910(6) _cell_length_c 23.2520(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.411(2) _cell_angle_gamma 90.00 _cell_volume 5134.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5402 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 27.550 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.392 _exptl_crystal_size_mid 0.244 _exptl_crystal_size_min 0.198 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2408.0 _exptl_absorpt_coefficient_mu 0.568 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.894 _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 none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 20964 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.55 _reflns_number_total 10574 _reflns_number_gt 8167 _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^)+(0.0593P)^2^+2.8924P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_number_reflns 5941 _refine_ls_number_parameters 758 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 -0.03694(6) 0.15673(2) 0.13042(3) 0.03525(15) Uani 1 1 d . . . Mn2 Mn 0.95656(6) -0.06504(2) -0.07643(3) 0.03615(16) Uani 1 1 d . . . N21 N 0.8869(4) -0.15062(14) -0.07068(17) 0.0423(9) Uani 1 1 d . . . N19 N 0.0208(4) 0.24432(13) 0.11983(15) 0.0369(8) Uani 1 1 d . . . N20 N -0.1586(4) 0.18531(15) 0.04411(16) 0.0430(9) Uani 1 1 d . . . N17 N -0.2589(4) 0.16976(15) 0.16631(17) 0.0423(9) Uani 1 1 d . . . C33 C 0.9143(5) -0.17367(17) -0.0173(2) 0.0439(11) Uani 1 1 d . . . N18 N -0.1520(4) 0.07552(14) 0.13532(16) 0.0392(8) Uani 1 1 d . . . N1 N 0.1630(4) 0.13205(15) 0.09021(17) 0.0446(7) Uani 1 1 d U . . N2 N 0.2097(4) 0.08160(16) 0.08374(18) 0.0472(10) Uani 1 1 d . . . C24 C -0.1333(5) 0.23582(18) 0.0281(2) 0.0429(10) Uani 1 1 d . . . C28 C -0.2597(6) 0.1557(2) 0.0108(2) 0.0567(14) Uani 1 1 d . . . H28 H -0.2781 0.1211 0.0225 0.068 Uiso 1 1 calc R . . C14 C -0.2808(5) 0.07447(18) 0.16019(19) 0.0403(10) Uani 1 1 d . . . C1 C 0.2535(5) 0.16533(17) 0.0688(2) 0.0429(8) Uani 1 1 d U . . H1 H 0.2438 0.2022 0.0690 0.051 Uiso 1 1 calc R . . C18 C -0.0907(5) 0.02853(18) 0.1218(2) 0.0473(11) Uani 1 1 d . . . H18 H -0.0006 0.0286 0.1053 0.057 Uiso 1 1 calc R . . C16 C -0.2856(7) -0.0202(2) 0.1580(2) 0.0585(14) Uani 1 1 d . . . H16 H -0.3289 -0.0525 0.1667 0.070 Uiso 1 1 calc R . . C13 C -0.3431(5) 0.12648(18) 0.1744(2) 0.0419(10) Uani 1 1 d . . . C12 C -0.4845(5) 0.1316(2) 0.1943(2) 0.0533(13) Uani 1 1 d . . . H12 H -0.5430 0.1018 0.2000 0.064 Uiso 1 1 calc R . . C9 C -0.3097(6) 0.21685(18) 0.1782(2) 0.0531(13) Uani 1 1 d . . . H9 H -0.2496 0.2464 0.1731 0.064 Uiso 1 1 calc R . . C15 C -0.3505(6) 0.02671(19) 0.1717(2) 0.0545(13) Uani 1 1 d . . . H15 H -0.4400 0.0267 0.1886 0.065 Uiso 1 1 calc R . . C10 C -0.4469(6) 0.2249(2) 0.1977(3) 0.0630(15) Uani 1 1 d . . . H10 H -0.4789 0.2591 0.2054 0.076 Uiso 1 1 calc R . . C11 C -0.5351(6) 0.1824(2) 0.2055(3) 0.0641(15) Uani 1 1 d . . . H11 H -0.6292 0.1871 0.2184 0.077 Uiso 1 1 calc R . . C17 C -0.1583(6) -0.0195(2) 0.1318(2) 0.0571(13) Uani 1 1 d . . . H17 H -0.1166 -0.0513 0.1206 0.069 Uiso 1 1 calc R . . N4 N 0.4077(4) 0.04024(16) 0.04151(17) 0.0469(9) Uani 1 1 d . . . N3 N 0.3611(5) 0.13891(18) 0.04679(19) 0.0566(11) Uani 1 1 d . . . C19 C 0.1184(6) 0.27074(18) 0.1582(2) 0.0484(11) Uani 1 1 d . . . H19 H 0.1492 0.2549 0.1939 0.058 Uiso 1 1 calc RD . . C20 C 0.1753(7) 0.3200(2) 0.1474(2) 0.0622(15) Uani 1 1 d . . . H20 H 0.2434 0.3373 0.1750 0.075 Uiso 1 1 calc R . . C21 C 0.1282(8) 0.3431(2) 0.0945(3) 0.0727(17) Uani 1 1 d . . . H21 H 0.1655 0.3763 0.0854 0.087 Uiso 1 1 calc R . . C25 C -0.2096(7) 0.2566(2) -0.0218(2) 0.0649(15) Uani 1 1 d . . . H25 H -0.1924 0.2916 -0.0324 0.078 Uiso 1 1 calc R . . C22 C 0.0254(7) 0.31666(19) 0.0550(2) 0.0604(14) Uani 1 1 d . . . H22 H -0.0089 0.3321 0.0193 0.072 Uiso 1 1 calc R . . C23 C -0.0261(5) 0.26716(17) 0.06896(19) 0.0422(10) Uani 1 1 d . . . C27 C -0.3380(7) 0.1744(3) -0.0403(3) 0.0708(16) Uani 1 1 d . . . H27 H -0.4065 0.1527 -0.0632 0.085 Uiso 1 1 calc R . . C26 C -0.3123(7) 0.2252(3) -0.0564(3) 0.0743(16) Uani 1 1 d . . . H26 H -0.3637 0.2389 -0.0906 0.089 Uiso 1 1 calc R . . C3 C 0.5892(5) 0.00417(17) 0.00004(19) 0.0384(9) Uani 1 1 d . . . C2 C 0.3318(5) 0.08799(19) 0.0576(2) 0.0434(10) Uani 1 1 d . . . N5 N 0.5127(4) 0.05088(16) 0.01534(17) 0.0475(9) Uani 1 1 d . . . N8 N 0.5656(5) -0.04695(16) 0.01208(19) 0.0528(10) Uani 1 1 d . . . N7 N 0.7025(4) 0.01030(16) -0.03049(18) 0.0488(10) Uani 1 1 d . . . N6 N 0.7526(4) -0.03863(15) -0.03721(17) 0.0457(9) Uani 1 1 d . . . C4 C 0.6708(5) -0.07268(15) -0.01161(19) 0.0382(10) Uani 1 1 d . . . H4 H 0.6852 -0.1094 -0.0104 0.046 Uiso 1 1 calc R . . N24 N 1.0866(4) 0.01205(13) -0.07412(16) 0.0395(8) Uani 1 1 d . . . N23 N 1.1720(4) -0.08194(15) -0.11333(16) 0.0385(8) Uani 1 1 d . . . C45 C 1.2876(5) 0.05820(18) -0.1108(2) 0.0464(11) Uani 1 1 d . . . H45 H 1.3755 0.0573 -0.1287 0.056 Uiso 1 1 calc R . . C44 C 1.2139(5) 0.01139(17) -0.09985(18) 0.0342(9) Uani 1 1 d . . . C48 C 1.0332(5) 0.05868(17) -0.0591(2) 0.0468(11) Uani 1 1 d . . . H48 H 0.9453 0.0590 -0.0412 0.056 Uiso 1 1 calc R . . C43 C 1.2686(5) -0.04151(17) -0.11652(18) 0.0352(9) Uani 1 1 d . . . C39 C 1.2143(5) -0.13142(18) -0.1284(2) 0.0438(11) Uani 1 1 d . . . H39 H 1.1480 -0.1597 -0.1258 0.053 Uiso 1 1 calc R . . C46 C 1.2297(6) 0.1061(2) -0.0951(2) 0.0547(13) Uani 1 1 d . . . H46 H 1.2777 0.1379 -0.1025 0.066 Uiso 1 1 calc R . . C42 C 1.4077(5) -0.0491(2) -0.1350(2) 0.0496(12) Uani 1 1 d . . . H42 H 1.4730 -0.0204 -0.1369 0.060 Uiso 1 1 calc R . . C47 C 1.1011(6) 0.10673(18) -0.0685(2) 0.0522(12) Uani 1 1 d . . . H47 H 1.0606 0.1386 -0.0571 0.063 Uiso 1 1 calc R . . N22 N 1.0644(4) -0.09600(15) 0.00996(17) 0.0442(9) Uani 1 1 d . . . C32 C 0.8485(7) -0.2212(2) -0.0056(3) 0.0704(16) Uani 1 1 d . . . H32 H 0.8680 -0.2365 0.0311 0.085 Uiso 1 1 calc R . . C38 C 1.1635(6) -0.0688(2) 0.0469(2) 0.0576(14) Uani 1 1 d . . . H38 H 1.1947 -0.0354 0.0356 0.069 Uiso 1 1 calc R . . C35 C 1.0719(8) -0.1643(2) 0.0805(3) 0.0752(17) Uani 1 1 d . . . H35 H 1.0389 -0.1974 0.0918 0.090 Uiso 1 1 calc R . . C34 C 1.0203(5) -0.14424(18) 0.0264(2) 0.0457(11) Uani 1 1 d . . . C31 C 0.7536(8) -0.2456(2) -0.0486(3) 0.0783(19) Uani 1 1 d . . . H31 H 0.7075 -0.2777 -0.0410 0.094 Uiso 1 1 calc R . . C29 C 0.7953(5) -0.1757(2) -0.1125(3) 0.0570(13) Uani 1 1 d . . . H29 H 0.7778 -0.1606 -0.1493 0.068 Uiso 1 1 calc R . . C37 C 1.2214(8) -0.0875(3) 0.1003(3) 0.0731(17) Uani 1 1 d . . . H37 H 1.2930 -0.0679 0.1243 0.088 Uiso 1 1 calc R . . C30 C 0.7260(7) -0.2238(2) -0.1019(4) 0.0767(19) Uani 1 1 d . . . H30 H 0.6617 -0.2407 -0.1310 0.092 Uiso 1 1 calc R . . C36 C 1.1719(9) -0.1351(3) 0.1174(3) 0.088(2) Uani 1 1 d . . . H36 H 1.2060 -0.1480 0.1543 0.106 Uiso 1 1 calc R . . C40 C 1.3524(6) -0.1411(2) -0.1476(2) 0.0533(12) Uani 1 1 d . . . H40 H 1.3782 -0.1753 -0.1583 0.064 Uiso 1 1 calc R . . C41 C 1.4508(6) -0.0994(2) -0.1506(2) 0.0610(14) Uani 1 1 d . . . H41 H 1.5452 -0.1048 -0.1630 0.073 Uiso 1 1 calc R . . O2 O 0.0803(4) 0.15878(11) 0.21796(15) 0.0469(8) Uani 1 1 d D . . O1 O 0.8414(4) -0.04639(16) -0.16417(15) 0.0547(9) Uani 1 1 d D . . C7 C 0.1296(5) 0.02569(18) 0.7538(2) 0.0464(8) Uani 1 1 d U . . N16 N 0.0599(4) -0.02064(14) 0.76090(15) 0.0427(6) Uani 1 1 d U . . N14 N 0.2757(4) -0.03258(14) 0.72794(16) 0.0445(6) Uani 1 1 d U . . N15 N 0.2603(5) 0.01966(15) 0.73357(17) 0.0517(10) Uani 1 1 d . . . C8 C 0.1561(5) -0.05621(16) 0.74417(19) 0.0410(6) Uani 1 1 d U . . H8 H 0.1408 -0.0929 0.7440 0.049 Uiso 1 1 calc R . . N12 N -0.0438(4) 0.07927(16) 0.78093(17) 0.0469(7) Uani 1 1 d U . . N13 N 0.0816(5) 0.07873(16) 0.76364(17) 0.0477(7) Uani 1 1 d U . . C6 C -0.0874(5) 0.13342(18) 0.7916(2) 0.0461(8) Uani 1 1 d U . . N11 N -0.0059(5) 0.17726(17) 0.7952(2) 0.0630(12) Uani 1 1 d . . . N10 N -0.2277(5) 0.14105(17) 0.8013(2) 0.0578(11) Uani 1 1 d . . . N9 N -0.2340(5) 0.19416(16) 0.8109(2) 0.0588(11) Uani 1 1 d . . . C5 C -0.1031(5) 0.21442(16) 0.8067(2) 0.0460(11) Uani 1 1 d . . . H5 H -0.0799 0.2504 0.8112 0.055 Uiso 1 1 calc R . . O3 O 0.0195(4) 0.23146(13) 0.29895(16) 0.0532(8) Uani 1 1 d D . . O5 O 0.6659(5) 0.04524(17) 0.8518(2) 0.0767(12) Uani 1 1 d D . . O6 O 0.4645(5) 0.1072(2) 0.7330(2) 0.0904(13) Uani 1 1 d D . . O4 O 0.8096(5) 0.31035(18) 0.2782(4) 0.120(2) Uani 1 1 d D . . H2 H 0.902(8) -0.041(4) -0.186(4) 0.179 Uiso 1 1 d D . . H3 H 0.773(8) -0.026(3) -0.166(4) 0.179 Uiso 1 1 d D . . H6 H 0.063(13) 0.179(2) 0.243(2) 0.179 Uiso 1 1 d D . . H7 H 0.057(11) 0.1687(13) 0.1849(10) 0.179 Uiso 1 1 d D . . H13 H 0.096(5) 0.245(3) 0.293(5) 0.179 Uiso 1 1 d D . . H14 H -0.052(6) 0.252(3) 0.294(5) 0.179 Uiso 1 1 d D . . H23 H 0.851(10) 0.336(2) 0.265(5) 0.179 Uiso 1 1 d D . . H24 H 0.733(7) 0.318(3) 0.290(5) 0.179 Uiso 1 1 d D . . H34 H 0.704(11) 0.047(4) 0.8853(15) 0.179 Uiso 1 1 d D . . H33 H 0.703(11) 0.068(3) 0.833(3) 0.179 Uiso 1 1 d D . . H44 H 0.422(11) 0.079(2) 0.740(4) 0.179 Uiso 1 1 d D . . H43 H 0.529(9) 0.113(4) 0.761(3) 0.179 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 Mn1 0.0363(3) 0.0277(3) 0.0436(4) 0.0016(3) 0.0122(3) -0.0009(3) Mn2 0.0372(3) 0.0295(3) 0.0434(4) -0.0007(3) 0.0113(3) -0.0042(3) N21 0.0364(18) 0.034(2) 0.059(2) -0.0073(18) 0.0150(17) 0.0003(15) N19 0.0458(19) 0.0306(18) 0.0360(19) 0.0026(15) 0.0122(16) -0.0015(15) N20 0.039(2) 0.046(2) 0.044(2) 0.0026(17) 0.0061(17) -0.0039(16) N17 0.042(2) 0.037(2) 0.051(2) -0.0007(17) 0.0174(18) -0.0032(16) C33 0.048(3) 0.024(2) 0.063(3) 0.000(2) 0.023(2) -0.0013(17) N18 0.0423(19) 0.034(2) 0.042(2) -0.0030(15) 0.0106(16) -0.0051(15) N1 0.0467(17) 0.0381(17) 0.0524(19) -0.0031(14) 0.0194(14) 0.0063(13) N2 0.044(2) 0.047(2) 0.053(2) -0.0023(18) 0.0156(19) 0.0064(17) C24 0.046(2) 0.043(3) 0.042(3) 0.002(2) 0.013(2) 0.0009(19) C28 0.053(3) 0.057(3) 0.058(3) -0.003(2) 0.001(3) -0.014(2) C14 0.040(2) 0.041(2) 0.039(2) 0.0019(19) 0.0030(19) -0.0077(19) C1 0.0458(17) 0.0354(17) 0.051(2) -0.0023(14) 0.0215(15) 0.0059(13) C18 0.050(3) 0.037(2) 0.055(3) -0.002(2) 0.011(2) -0.0024(19) C16 0.076(4) 0.030(2) 0.072(4) 0.005(2) 0.019(3) -0.013(2) C13 0.036(2) 0.041(2) 0.049(3) 0.007(2) 0.0096(19) -0.0036(18) C12 0.042(3) 0.059(3) 0.062(3) 0.003(3) 0.019(2) -0.011(2) C9 0.053(3) 0.036(3) 0.076(4) 0.004(2) 0.028(3) 0.003(2) C15 0.061(3) 0.045(3) 0.060(3) 0.003(2) 0.016(2) -0.022(2) C10 0.064(3) 0.048(3) 0.084(4) 0.001(3) 0.035(3) 0.007(2) C11 0.044(3) 0.067(3) 0.086(4) 0.000(3) 0.026(3) 0.009(3) C17 0.068(3) 0.034(3) 0.070(4) -0.005(2) 0.012(3) -0.005(2) N4 0.040(2) 0.052(2) 0.050(2) 0.0025(19) 0.0094(18) -0.0050(17) N3 0.055(2) 0.057(3) 0.063(3) -0.005(2) 0.027(2) 0.000(2) C19 0.064(3) 0.037(2) 0.046(3) 0.002(2) 0.011(2) -0.006(2) C20 0.093(4) 0.040(3) 0.056(3) -0.010(2) 0.018(3) -0.024(3) C21 0.113(5) 0.042(3) 0.063(4) 0.000(3) 0.014(3) -0.028(3) C25 0.090(4) 0.048(3) 0.054(3) 0.012(2) -0.004(3) 0.005(3) C22 0.093(4) 0.041(3) 0.049(3) 0.009(2) 0.013(3) -0.011(3) C23 0.057(3) 0.032(2) 0.042(3) 0.0030(18) 0.020(2) 0.0049(19) C27 0.064(3) 0.088(4) 0.056(4) -0.015(3) -0.009(3) -0.013(3) C26 0.085(4) 0.081(4) 0.052(3) 0.003(3) -0.008(3) 0.009(3) C3 0.042(2) 0.036(2) 0.036(2) -0.0016(18) 0.0054(19) 0.0057(18) C2 0.047(2) 0.043(3) 0.040(3) -0.0050(19) 0.005(2) 0.005(2) N5 0.040(2) 0.055(2) 0.049(2) -0.0036(19) 0.0129(18) -0.0072(17) N8 0.059(2) 0.046(2) 0.059(3) 0.006(2) 0.030(2) 0.005(2) N7 0.049(2) 0.045(2) 0.056(3) -0.0008(19) 0.020(2) 0.0026(17) N6 0.051(2) 0.040(2) 0.049(2) -0.0030(17) 0.0179(18) 0.0062(17) C4 0.052(2) 0.0200(18) 0.048(3) 0.0078(17) 0.027(2) 0.0071(17) N24 0.0421(19) 0.0308(19) 0.046(2) -0.0031(15) 0.0087(16) -0.0070(15) N23 0.0357(19) 0.038(2) 0.042(2) 0.0047(17) 0.0059(16) 0.0002(16) C45 0.044(2) 0.044(3) 0.050(3) -0.002(2) 0.005(2) -0.009(2) C44 0.034(2) 0.036(2) 0.031(2) 0.0011(17) 0.0001(17) -0.0052(16) C48 0.049(3) 0.035(2) 0.058(3) -0.005(2) 0.016(2) -0.005(2) C43 0.036(2) 0.034(2) 0.035(2) 0.0009(17) 0.0010(18) -0.0016(17) C39 0.051(3) 0.033(2) 0.049(3) -0.002(2) 0.010(2) 0.005(2) C46 0.059(3) 0.040(3) 0.063(3) 0.002(2) 0.000(3) -0.018(2) C42 0.037(2) 0.051(3) 0.062(3) -0.002(2) 0.009(2) -0.009(2) C47 0.060(3) 0.032(2) 0.063(3) -0.009(2) 0.004(2) -0.004(2) N22 0.048(2) 0.039(2) 0.046(2) -0.0022(17) 0.0079(18) -0.0029(16) C32 0.089(4) 0.036(3) 0.093(4) 0.001(3) 0.038(4) -0.011(3) C38 0.062(3) 0.059(3) 0.051(3) -0.002(2) 0.006(3) -0.009(2) C35 0.101(5) 0.060(4) 0.065(4) 0.014(3) 0.010(3) 0.006(3) C34 0.055(3) 0.036(2) 0.049(3) 0.005(2) 0.019(2) 0.007(2) C31 0.096(5) 0.035(3) 0.111(5) -0.010(3) 0.039(4) -0.028(3) C29 0.050(3) 0.046(3) 0.075(4) -0.024(3) 0.009(3) -0.004(2) C37 0.079(4) 0.081(4) 0.057(4) -0.011(3) -0.004(3) 0.004(3) C30 0.059(3) 0.054(4) 0.117(6) -0.039(4) 0.015(4) -0.018(3) C36 0.109(5) 0.099(5) 0.050(4) 0.018(4) -0.014(4) 0.015(4) C40 0.052(3) 0.047(3) 0.063(3) -0.003(2) 0.016(2) 0.013(2) C41 0.038(3) 0.078(4) 0.069(4) -0.005(3) 0.014(2) 0.010(2) O2 0.0541(18) 0.0422(18) 0.0447(19) 0.0052(14) 0.0069(16) 0.0040(14) O1 0.0435(19) 0.072(2) 0.049(2) 0.0054(18) 0.0060(16) -0.0050(16) C7 0.0506(18) 0.0429(17) 0.0468(18) -0.0009(14) 0.0100(15) 0.0031(14) N16 0.0509(15) 0.0353(14) 0.0417(14) -0.0001(11) 0.0049(12) 0.0023(11) N14 0.0535(15) 0.0358(14) 0.0445(14) -0.0031(11) 0.0071(12) 0.0060(11) N15 0.061(2) 0.039(2) 0.056(3) -0.0024(18) 0.012(2) 0.0023(18) C8 0.0504(14) 0.0319(13) 0.0408(13) -0.0016(11) 0.0058(11) 0.0038(10) N12 0.0465(17) 0.0454(17) 0.0493(18) 0.0034(14) 0.0081(14) -0.0011(14) N13 0.0506(17) 0.0456(17) 0.0483(18) -0.0003(14) 0.0113(15) 0.0022(14) C6 0.0466(18) 0.0438(17) 0.0483(19) 0.0032(15) 0.0077(15) 0.0005(14) N11 0.052(2) 0.047(2) 0.094(3) 0.006(2) 0.024(2) 0.0030(19) N10 0.050(2) 0.050(2) 0.075(3) 0.003(2) 0.017(2) 0.0020(19) N9 0.063(3) 0.043(2) 0.074(3) 0.002(2) 0.023(2) 0.018(2) C5 0.047(2) 0.0178(19) 0.076(3) 0.001(2) 0.018(2) 0.0015(17) O3 0.0549(19) 0.0474(19) 0.059(2) 0.0005(16) 0.0135(17) -0.0007(15) O5 0.065(2) 0.072(3) 0.093(3) 0.024(2) 0.011(2) -0.012(2) O6 0.069(3) 0.094(3) 0.105(4) 0.004(3) -0.002(2) -0.021(2) O4 0.061(3) 0.067(3) 0.236(7) 0.016(4) 0.040(4) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 2.164(4) . ? Mn1 N1 2.199(4) . ? Mn1 N17 2.260(4) . ? Mn1 N20 2.269(4) . ? Mn1 N19 2.277(3) . ? Mn1 N18 2.288(3) . ? Mn1 H7 1.45(5) . ? Mn2 O1 2.211(3) . ? Mn2 N6 2.230(4) . ? Mn2 N23 2.234(3) . ? Mn2 N21 2.243(4) . ? Mn2 N22 2.249(4) . ? Mn2 N24 2.250(3) . ? N21 C29 1.340(6) . ? N21 C33 1.362(6) . ? N19 C23 1.332(5) . ? N19 C19 1.336(6) . ? N20 C28 1.333(6) . ? N20 C24 1.348(6) . ? N17 C9 1.307(6) . ? N17 C13 1.345(5) . ? C33 C32 1.370(6) . ? C33 C34 1.489(7) . ? N18 C14 1.346(6) . ? N18 C18 1.353(6) . ? N1 C1 1.302(6) . ? N1 N2 1.347(5) . ? N2 C2 1.319(6) . ? C24 C25 1.369(7) . ? C24 C23 1.481(6) . ? C28 C27 1.379(8) . ? C28 H28 0.9300 . ? C14 C15 1.391(6) . ? C14 C13 1.471(6) . ? C1 N3 1.318(6) . ? C1 H1 0.9300 . ? C18 C17 1.380(7) . ? C18 H18 0.9300 . ? C16 C17 1.351(8) . ? C16 C15 1.366(7) . ? C16 H16 0.9300 . ? C13 C12 1.399(6) . ? C12 C11 1.386(7) . ? C12 H12 0.9300 . ? C9 C10 1.368(7) . ? C9 H9 0.9300 . ? C15 H15 0.9300 . ? C10 C11 1.348(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C17 H17 0.9300 . ? N4 N5 1.207(4) . ? N4 C2 1.447(6) . ? N3 C2 1.334(6) . ? C19 C20 1.371(7) . ? C19 H19 0.9300 . ? C20 C21 1.376(8) . ? C20 H20 0.9300 . ? C21 C22 1.378(8) . ? C21 H21 0.9300 . ? C25 C26 1.381(8) . ? C25 H25 0.9300 . ? C22 C23 1.376(6) . ? C22 H22 0.9300 . ? C27 C26 1.357(9) . ? C27 H27 0.9300 . ? C26 H26 0.9300 . ? C3 N7 1.313(6) . ? C3 N8 1.335(6) . ? C3 N5 1.422(5) . ? N8 C4 1.314(5) . ? N7 N6 1.322(5) . ? N6 C4 1.313(5) . ? C4 H4 0.9300 . ? N24 C48 1.326(5) . ? N24 C44 1.345(5) . ? N23 C43 1.337(5) . ? N23 C39 1.357(6) . ? C45 C46 1.375(7) . ? C45 C44 1.384(6) . ? C45 H45 0.9300 . ? C44 C43 1.482(6) . ? C48 C47 1.378(6) . ? C48 H48 0.9300 . ? C43 C42 1.371(6) . ? C39 C40 1.378(7) . ? C39 H39 0.9300 . ? C46 C47 1.367(7) . ? C46 H46 0.9300 . ? C42 C41 1.380(7) . ? C42 H42 0.9300 . ? C47 H47 0.9300 . ? N22 C38 1.335(7) . ? N22 C34 1.342(6) . ? C32 C31 1.368(9) . ? C32 H32 0.9300 . ? C38 C37 1.365(8) . ? C38 H38 0.9300 . ? C35 C36 1.366(9) . ? C35 C34 1.378(8) . ? C35 H35 0.9300 . ? C31 C30 1.347(10) . ? C31 H31 0.9300 . ? C29 C30 1.393(8) . ? C29 H29 0.9300 . ? C37 C36 1.350(9) . ? C37 H37 0.9300 . ? C30 H30 0.9300 . ? C36 H36 0.9300 . ? C40 C41 1.372(7) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? O2 H6 0.80(2) . ? O2 H7 0.81(4) . ? O1 H2 0.79(2) . ? O1 H3 0.79(2) . ? C7 N15 1.315(6) . ? C7 N16 1.337(6) . ? C7 N13 1.425(6) . ? N16 C8 1.327(5) . ? N14 C8 1.313(6) . ? N14 N15 1.326(5) . ? C8 H8 0.9300 . ? N12 N13 1.231(5) . ? N12 C6 1.443(6) . ? C6 N10 1.307(6) . ? C6 N11 1.313(6) . ? N11 C5 1.321(6) . ? N10 N9 1.353(6) . ? N9 C5 1.282(6) . ? C5 H5 0.9300 . ? O3 H13 0.80(2) . ? O3 H14 0.81(2) . ? O5 H34 0.81(2) . ? O5 H33 0.81(2) . ? O6 H44 0.83(2) . ? O6 H43 0.82(2) . ? O4 H23 0.80(2) . ? O4 H24 0.79(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 N1 95.17(14) . . ? O2 Mn1 N17 89.18(14) . . ? N1 Mn1 N17 170.91(14) . . ? O2 Mn1 N20 160.17(13) . . ? N1 Mn1 N20 91.77(14) . . ? N17 Mn1 N20 86.72(14) . . ? O2 Mn1 N19 89.49(12) . . ? N1 Mn1 N19 91.18(13) . . ? N17 Mn1 N19 96.85(13) . . ? N20 Mn1 N19 71.78(13) . . ? O2 Mn1 N18 97.93(12) . . ? N1 Mn1 N18 99.22(13) . . ? N17 Mn1 N18 72.23(13) . . ? N20 Mn1 N18 99.26(13) . . ? N19 Mn1 N18 166.59(13) . . ? O2 Mn1 H7 12.6(10) . . ? N1 Mn1 H7 92(4) . . ? N17 Mn1 H7 94(4) . . ? N20 Mn1 H7 149.1(11) . . ? N19 Mn1 H7 77.5(9) . . ? N18 Mn1 H7 110.5(8) . . ? O1 Mn2 N6 90.65(14) . . ? O1 Mn2 N23 90.15(13) . . ? N6 Mn2 N23 173.26(14) . . ? O1 Mn2 N21 99.17(14) . . ? N6 Mn2 N21 90.89(13) . . ? N23 Mn2 N21 95.59(13) . . ? O1 Mn2 N22 171.92(14) . . ? N6 Mn2 N22 90.67(14) . . ? N23 Mn2 N22 89.47(13) . . ? N21 Mn2 N22 72.84(14) . . ? O1 Mn2 N24 90.85(13) . . ? N6 Mn2 N24 100.12(13) . . ? N23 Mn2 N24 73.18(13) . . ? N21 Mn2 N24 165.05(13) . . ? N22 Mn2 N24 96.76(13) . . ? C29 N21 C33 118.8(4) . . ? C29 N21 Mn2 123.5(4) . . ? C33 N21 Mn2 116.3(3) . . ? C23 N19 C19 118.7(4) . . ? C23 N19 Mn1 117.5(3) . . ? C19 N19 Mn1 122.8(3) . . ? C28 N20 C24 119.1(4) . . ? C28 N20 Mn1 123.1(3) . . ? C24 N20 Mn1 117.7(3) . . ? C9 N17 C13 119.2(4) . . ? C9 N17 Mn1 123.4(3) . . ? C13 N17 Mn1 117.4(3) . . ? N21 C33 C32 121.4(5) . . ? N21 C33 C34 115.7(4) . . ? C32 C33 C34 122.9(5) . . ? C14 N18 C18 118.2(4) . . ? C14 N18 Mn1 116.6(3) . . ? C18 N18 Mn1 124.7(3) . . ? C1 N1 N2 110.2(4) . . ? C1 N1 Mn1 123.6(3) . . ? N2 N1 Mn1 126.1(3) . . ? C2 N2 N1 102.7(4) . . ? N20 C24 C25 120.7(4) . . ? N20 C24 C23 116.0(4) . . ? C25 C24 C23 123.3(4) . . ? N20 C28 C27 122.6(5) . . ? N20 C28 H28 118.7 . . ? C27 C28 H28 118.7 . . ? N18 C14 C15 121.5(4) . . ? N18 C14 C13 116.3(4) . . ? C15 C14 C13 122.1(4) . . ? N1 C1 N3 109.8(4) . . ? N1 C1 H1 125.1 . . ? N3 C1 H1 125.1 . . ? N18 C18 C17 121.7(4) . . ? N18 C18 H18 119.1 . . ? C17 C18 H18 119.2 . . ? C17 C16 C15 119.8(5) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N17 C13 C12 120.6(4) . . ? N17 C13 C14 117.0(4) . . ? C12 C13 C14 122.4(4) . . ? C11 C12 C13 118.3(5) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? N17 C9 C10 123.3(5) . . ? N17 C9 H9 118.4 . . ? C10 C9 H9 118.3 . . ? C16 C15 C14 119.1(5) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.4 . . ? C11 C10 C9 119.1(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 119.5(5) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C16 C17 C18 119.6(5) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? N5 N4 C2 111.3(4) . . ? C1 N3 C2 103.9(4) . . ? N19 C19 C20 123.3(5) . . ? N19 C19 H19 118.4 . . ? C20 C19 H19 118.3 . . ? C19 C20 C21 117.8(5) . . ? C19 C20 H20 121.1 . . ? C21 C20 H20 121.1 . . ? C20 C21 C22 119.5(5) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.3 . . ? C24 C25 C26 119.6(5) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C23 C22 C21 119.2(5) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? N19 C23 C22 121.5(5) . . ? N19 C23 C24 116.3(4) . . ? C22 C23 C24 122.2(4) . . ? C26 C27 C28 118.2(5) . . ? C26 C27 H27 120.9 . . ? C28 C27 H27 120.9 . . ? C27 C26 C25 119.8(5) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? N7 C3 N8 112.2(4) . . ? N7 C3 N5 117.5(4) . . ? N8 C3 N5 130.2(4) . . ? N2 C2 N3 113.3(4) . . ? N2 C2 N4 117.1(4) . . ? N3 C2 N4 129.5(4) . . ? N4 N5 C3 111.6(4) . . ? C4 N8 C3 104.2(4) . . ? C3 N7 N6 104.4(4) . . ? C4 N6 N7 109.7(4) . . ? C4 N6 Mn2 121.2(3) . . ? N7 N6 Mn2 128.9(3) . . ? N6 C4 N8 109.6(4) . . ? N6 C4 H4 125.2 . . ? N8 C4 H4 125.2 . . ? C48 N24 C44 118.5(4) . . ? C48 N24 Mn2 124.4(3) . . ? C44 N24 Mn2 115.9(3) . . ? C43 N23 C39 118.6(4) . . ? C43 N23 Mn2 117.7(3) . . ? C39 N23 Mn2 123.6(3) . . ? C46 C45 C44 119.4(4) . . ? C46 C45 H45 120.3 . . ? C44 C45 H45 120.3 . . ? N24 C44 C45 121.0(4) . . ? N24 C44 C43 116.7(4) . . ? C45 C44 C43 122.2(4) . . ? N24 C48 C47 123.5(4) . . ? N24 C48 H48 118.3 . . ? C47 C48 H48 118.3 . . ? N23 C43 C42 121.5(4) . . ? N23 C43 C44 115.5(4) . . ? C42 C43 C44 123.0(4) . . ? N23 C39 C40 122.2(4) . . ? N23 C39 H39 118.9 . . ? C40 C39 H39 118.9 . . ? C47 C46 C45 119.5(5) . . ? C47 C46 H46 120.2 . . ? C45 C46 H46 120.3 . . ? C43 C42 C41 120.1(4) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C46 C47 C48 118.0(5) . . ? C46 C47 H47 121.0 . . ? C48 C47 H47 121.0 . . ? C38 N22 C34 118.1(4) . . ? C38 N22 Mn2 124.5(3) . . ? C34 N22 Mn2 117.3(3) . . ? C31 C32 C33 118.8(6) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? N22 C38 C37 123.3(5) . . ? N22 C38 H38 118.3 . . ? C37 C38 H38 118.4 . . ? C36 C35 C34 119.4(6) . . ? C36 C35 H35 120.3 . . ? C34 C35 H35 120.3 . . ? N22 C34 C35 121.0(5) . . ? N22 C34 C33 115.8(4) . . ? C35 C34 C33 123.2(5) . . ? C30 C31 C32 120.8(5) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? N21 C29 C30 121.2(6) . . ? N21 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C36 C37 C38 118.3(6) . . ? C36 C37 H37 120.9 . . ? C38 C37 H37 120.9 . . ? C31 C30 C29 118.9(6) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.6 . . ? C37 C36 C35 119.9(6) . . ? C37 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C41 C40 C39 118.6(5) . . ? C41 C40 H40 120.7 . . ? C39 C40 H40 120.7 . . ? C40 C41 C42 119.0(4) . . ? C40 C41 H41 120.5 . . ? C42 C41 H41 120.5 . . ? Mn1 O2 H6 126(7) . . ? Mn1 O2 H7 23(3) . . ? H6 O2 H7 116(5) . . ? Mn2 O1 H2 110(7) . . ? Mn2 O1 H3 116(7) . . ? H2 O1 H3 116(4) . . ? N15 C7 N16 112.8(4) . . ? N15 C7 N13 117.4(4) . . ? N16 C7 N13 129.8(4) . . ? C8 N16 C7 102.9(4) . . ? C8 N14 N15 108.7(4) . . ? C7 N15 N14 104.8(4) . . ? N14 C8 N16 110.8(4) . . ? N14 C8 H8 124.6 . . ? N16 C8 H8 124.6 . . ? N13 N12 C6 109.9(4) . . ? N12 N13 C7 111.4(4) . . ? N10 C6 N11 113.3(4) . . ? N10 C6 N12 116.8(4) . . ? N11 C6 N12 129.9(4) . . ? C6 N11 C5 103.6(4) . . ? C6 N10 N9 103.5(4) . . ? C5 N9 N10 108.7(4) . . ? N9 C5 N11 110.9(4) . . ? N9 C5 H5 124.5 . . ? N11 C5 H5 124.5 . . ? H13 O3 H14 112(4) . . ? H34 O5 H33 109(4) . . ? H44 O6 H43 106(3) . . ? H23 O4 H24 112(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.638 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 920313'