# 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 Cu3 N4 O12' _chemical_formula_weight 775.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.0747(17) _cell_length_b 11.8777(11) _cell_length_c 12.5442(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2693.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4283 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 26.99 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1564 _exptl_absorpt_coefficient_mu 2.424 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6559 _exptl_absorpt_correction_T_max 0.7434 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17246 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2500 _reflns_number_gt 2073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0356P)^2^+1.5499P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2500 _refine_ls_number_parameters 205 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0664 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.477002(16) 0.10148(2) 0.44123(3) 0.01852(11) Uani 1 1 d . . . Cu2 Cu 0.5000 -0.07454(3) 0.2500 0.01763(12) Uani 1 2 d S . . O1 O 0.42693(9) 0.04247(15) 0.20175(14) 0.0243(4) Uani 1 1 d . . . O2 O 0.39145(9) 0.13321(14) 0.34932(14) 0.0229(4) Uani 1 1 d . . . O3 O 0.15537(10) 0.34739(18) 0.35011(16) 0.0369(5) Uani 1 1 d . . . O4 O 0.07511(9) 0.31199(16) 0.21835(15) 0.0271(4) Uani 1 1 d . . . O5 O 0.19662(11) 0.06804(19) -0.03434(16) 0.0359(5) Uani 1 1 d U . . O6 O 0.46390(9) -0.05894(15) 0.43725(14) 0.0208(4) Uani 1 1 d . . . H1W H 0.4229 -0.0919 0.4262 0.031 Uiso 1 1 d R . . N1 N 0.50426(12) 0.26293(18) 0.42832(17) 0.0242(5) Uani 1 1 d . . . N2 N 0.50531(13) 0.43645(18) 0.3668(2) 0.0287(5) Uani 1 1 d . . . C1 C 0.38242(13) 0.1022(2) 0.2543(2) 0.0186(5) Uani 1 1 d . . . C2 C 0.31134(13) 0.1377(2) 0.2003(2) 0.0182(5) Uani 1 1 d . . . C3 C 0.26373(13) 0.2133(2) 0.2499(2) 0.0190(5) Uani 1 1 d . . . H3 H 0.2775 0.2480 0.3133 0.023 Uiso 1 1 calc R . . C4 C 0.19496(13) 0.2367(2) 0.2039(2) 0.0193(5) Uani 1 1 d . . . C5 C 0.17654(13) 0.1884(2) 0.1076(2) 0.0219(6) Uani 1 1 d . . . H5 H 0.1316 0.2065 0.0756 0.026 Uiso 1 1 calc R . . C6 C 0.22386(15) 0.1135(2) 0.0576(2) 0.0237(6) Uani 1 1 d . . . C7 C 0.29156(14) 0.0869(2) 0.1040(2) 0.0222(6) Uani 1 1 d . . . H7 H 0.3233 0.0359 0.0712 0.027 Uiso 1 1 calc R . . C8 C 0.13817(13) 0.3060(2) 0.2630(2) 0.0224(6) Uani 1 1 d . . . C9 C 0.23181(18) -0.0300(3) -0.0747(3) 0.0524(10) Uani 1 1 d U . . H9A H 0.2811 -0.0115 -0.0973 0.079 Uiso 1 1 calc R . . H9B H 0.2042 -0.0585 -0.1343 0.079 Uiso 1 1 calc R . . H9C H 0.2339 -0.0863 -0.0199 0.079 Uiso 1 1 calc R . . C10 C 0.57076(17) 0.3123(2) 0.4537(2) 0.0341(7) Uani 1 1 d . . . H10 H 0.6091 0.2780 0.4911 0.041 Uiso 1 1 calc R . . C11 C 0.57145(19) 0.4188(3) 0.4157(3) 0.0411(8) Uani 1 1 d . . . H11 H 0.6099 0.4703 0.4219 0.049 Uiso 1 1 calc R . . C12 C 0.46695(15) 0.3406(2) 0.3757(2) 0.0273(6) Uani 1 1 d . . . H12 H 0.4197 0.3300 0.3481 0.033 Uiso 1 1 calc R . . C13 C 0.48362(18) 0.5362(2) 0.3054(2) 0.0349(7) Uani 1 1 d . . . H13A H 0.4998 0.6033 0.3429 0.042 Uiso 1 1 calc R . . H13B H 0.4301 0.5389 0.3001 0.042 Uiso 1 1 calc 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 Cu1 0.01593(17) 0.01836(17) 0.02127(19) 0.00012(12) -0.00384(12) -0.00163(11) Cu2 0.0081(2) 0.0158(2) 0.0290(3) 0.000 -0.00181(17) 0.000 O1 0.0159(9) 0.0319(10) 0.0250(10) 0.0018(8) 0.0021(8) 0.0098(8) O2 0.0175(9) 0.0262(10) 0.0250(11) -0.0023(8) -0.0055(7) 0.0034(7) O3 0.0230(10) 0.0573(14) 0.0302(12) -0.0188(10) -0.0030(9) 0.0166(9) O4 0.0132(9) 0.0305(10) 0.0376(12) -0.0093(8) -0.0033(8) 0.0052(7) O5 0.0226(10) 0.0531(13) 0.0321(12) -0.0193(10) -0.0047(9) 0.0063(9) O6 0.0169(9) 0.0212(9) 0.0242(10) 0.0011(7) -0.0064(7) -0.0054(7) N1 0.0237(12) 0.0209(11) 0.0281(13) -0.0003(9) -0.0028(10) -0.0006(9) N2 0.0337(13) 0.0217(11) 0.0307(14) -0.0006(10) -0.0029(11) -0.0001(10) C1 0.0128(12) 0.0179(13) 0.0253(15) 0.0057(11) 0.0010(10) 0.0003(9) C2 0.0120(12) 0.0206(13) 0.0219(14) 0.0043(11) 0.0007(10) 0.0024(10) C3 0.0165(13) 0.0203(13) 0.0201(14) -0.0006(10) 0.0017(10) 0.0008(10) C4 0.0157(12) 0.0204(13) 0.0217(14) 0.0025(11) 0.0019(10) 0.0028(10) C5 0.0131(12) 0.0275(14) 0.0250(15) 0.0005(11) -0.0026(10) 0.0046(10) C6 0.0194(13) 0.0287(14) 0.0231(14) -0.0052(11) -0.0023(11) -0.0003(11) C7 0.0170(13) 0.0236(14) 0.0260(15) -0.0036(11) 0.0027(11) 0.0048(10) C8 0.0151(13) 0.0227(14) 0.0295(16) 0.0001(11) 0.0042(11) 0.0026(10) C9 0.0330(18) 0.060(2) 0.064(2) -0.0413(19) 0.0017(16) 0.0042(16) C10 0.0325(16) 0.0288(16) 0.0411(19) 0.0012(13) -0.0128(14) -0.0042(13) C11 0.0411(19) 0.0293(17) 0.053(2) 0.0045(14) -0.0138(16) -0.0129(14) C12 0.0248(14) 0.0228(14) 0.0342(17) 0.0013(12) 0.0003(12) -0.0011(11) C13 0.0486(19) 0.0194(14) 0.0367(18) -0.0019(13) 0.0004(14) 0.0048(13) _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 O6 1.9208(18) . ? Cu1 O6 1.9288(17) 5_656 ? Cu1 O2 1.9653(17) . ? Cu1 N1 1.987(2) . ? Cu1 Cu1 2.9457(6) 5_656 ? Cu2 O4 1.9538(17) 6_656 ? Cu2 O4 1.9538(17) 8_655 ? Cu2 O1 2.0106(17) 3_655 ? Cu2 O1 2.0106(17) . ? Cu2 O6 2.4448(18) . ? O1 C1 1.258(3) . ? O2 C1 1.259(3) . ? O3 C8 1.238(3) . ? O4 C8 1.272(3) . ? O4 Cu2 1.9538(17) 6_566 ? O5 C6 1.366(3) . ? O5 C9 1.420(4) . ? O6 Cu1 1.9288(17) 5_656 ? O6 H1W 0.8501 . ? N1 C12 1.320(3) . ? N1 C10 1.375(4) . ? N2 C12 1.338(3) . ? N2 C11 1.361(4) . ? N2 C13 1.467(4) . ? C1 C2 1.512(3) . ? C2 C3 1.390(3) . ? C2 C7 1.397(4) . ? C3 C4 1.399(3) . ? C3 H3 0.9300 . ? C4 C5 1.378(4) . ? C4 C8 1.510(3) . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 C7 1.391(4) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.351(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C13 1.511(6) 3_655 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Cu1 O6 80.15(8) . 5_656 ? O6 Cu1 O2 94.47(7) . . ? O6 Cu1 O2 161.74(8) 5_656 . ? O6 Cu1 N1 170.43(9) . . ? O6 Cu1 N1 100.37(8) 5_656 . ? O2 Cu1 N1 87.84(8) . . ? O6 Cu1 Cu1 40.17(5) . 5_656 ? O6 Cu1 Cu1 39.97(5) 5_656 5_656 ? O2 Cu1 Cu1 132.27(5) . 5_656 ? N1 Cu1 Cu1 139.54(7) . 5_656 ? O4 Cu2 O4 92.76(11) 6_656 8_655 ? O4 Cu2 O1 87.66(8) 6_656 3_655 ? O4 Cu2 O1 173.99(7) 8_655 3_655 ? O4 Cu2 O1 173.99(7) 6_656 . ? O4 Cu2 O1 87.66(8) 8_655 . ? O1 Cu2 O1 92.54(11) 3_655 . ? O4 Cu2 O6 92.43(7) 6_656 . ? O4 Cu2 O6 93.56(7) 8_655 . ? O1 Cu2 O6 80.43(6) 3_655 . ? O1 Cu2 O6 93.53(6) . . ? C1 O1 Cu2 130.68(17) . . ? C1 O2 Cu1 126.98(16) . . ? C8 O4 Cu2 124.88(17) . 6_566 ? C6 O5 C9 117.7(2) . . ? Cu1 O6 Cu1 99.85(8) . 5_656 ? Cu1 O6 Cu2 93.86(7) . . ? Cu1 O6 Cu2 126.28(8) 5_656 . ? Cu1 O6 H1W 124.7 . . ? Cu1 O6 H1W 119.4 5_656 . ? Cu2 O6 H1W 92.4 . . ? C12 N1 C10 105.3(2) . . ? C12 N1 Cu1 126.07(19) . . ? C10 N1 Cu1 127.57(19) . . ? C12 N2 C11 106.6(2) . . ? C12 N2 C13 126.4(2) . . ? C11 N2 C13 126.6(3) . . ? O1 C1 O2 125.3(2) . . ? O1 C1 C2 117.8(2) . . ? O2 C1 C2 116.9(2) . . ? C3 C2 C7 120.5(2) . . ? C3 C2 C1 120.4(2) . . ? C7 C2 C1 118.9(2) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 C8 119.5(2) . . ? C3 C4 C8 120.6(2) . . ? C4 C5 C6 121.0(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? O5 C6 C5 114.5(2) . . ? O5 C6 C7 125.5(2) . . ? C5 C6 C7 120.0(2) . . ? C6 C7 C2 119.2(2) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? O3 C8 O4 126.3(2) . . ? O3 C8 C4 118.6(2) . . ? O4 C8 C4 115.1(2) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N1 109.0(3) . . ? C11 C10 H10 125.5 . . ? N1 C10 H10 125.5 . . ? C10 C11 N2 107.2(3) . . ? C10 C11 H11 126.4 . . ? N2 C11 H11 126.4 . . ? N1 C12 N2 111.8(2) . . ? N1 C12 H12 124.1 . . ? N2 C12 H12 124.1 . . ? N2 C13 C13 112.2(2) . 3_655 ? N2 C13 H13A 109.2 . . ? C13 C13 H13A 109.2 3_655 . ? N2 C13 H13B 109.2 . . ? C13 C13 H13B 109.2 3_655 . ? H13A C13 H13B 107.9 . . ? 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 O4 Cu2 O1 C1 -169.9(7) 6_656 . . . ? O4 Cu2 O1 C1 95.9(2) 8_655 . . . ? O1 Cu2 O1 C1 -78.1(2) 3_655 . . . ? O6 Cu2 O1 C1 2.4(2) . . . . ? O6 Cu1 O2 C1 -61.6(2) . . . . ? O6 Cu1 O2 C1 -133.6(2) 5_656 . . . ? N1 Cu1 O2 C1 109.0(2) . . . . ? Cu1 Cu1 O2 C1 -76.9(2) 5_656 . . . ? O6 Cu1 O6 Cu1 0.0 5_656 . . 5_656 ? O2 Cu1 O6 Cu1 -162.40(8) . . . 5_656 ? N1 Cu1 O6 Cu1 93.9(5) . . . 5_656 ? O6 Cu1 O6 Cu2 -127.85(10) 5_656 . . . ? O2 Cu1 O6 Cu2 69.74(7) . . . . ? N1 Cu1 O6 Cu2 -33.9(5) . . . . ? Cu1 Cu1 O6 Cu2 -127.85(10) 5_656 . . . ? O4 Cu2 O6 Cu1 126.33(8) 6_656 . . . ? O4 Cu2 O6 Cu1 -140.75(8) 8_655 . . . ? O1 Cu2 O6 Cu1 39.11(7) 3_655 . . . ? O1 Cu2 O6 Cu1 -52.87(8) . . . . ? O4 Cu2 O6 Cu1 21.13(11) 6_656 . . 5_656 ? O4 Cu2 O6 Cu1 114.05(11) 8_655 . . 5_656 ? O1 Cu2 O6 Cu1 -66.09(10) 3_655 . . 5_656 ? O1 Cu2 O6 Cu1 -158.07(11) . . . 5_656 ? O6 Cu1 N1 C12 105.9(5) . . . . ? O6 Cu1 N1 C12 -161.9(2) 5_656 . . . ? O2 Cu1 N1 C12 1.7(2) . . . . ? Cu1 Cu1 N1 C12 -171.48(18) 5_656 . . . ? O6 Cu1 N1 C10 -60.8(6) . . . . ? O6 Cu1 N1 C10 31.4(2) 5_656 . . . ? O2 Cu1 N1 C10 -165.0(2) . . . . ? Cu1 Cu1 N1 C10 21.8(3) 5_656 . . . ? Cu2 O1 C1 O2 28.4(4) . . . . ? Cu2 O1 C1 C2 -150.17(17) . . . . ? Cu1 O2 C1 O1 1.5(4) . . . . ? Cu1 O2 C1 C2 -179.92(15) . . . . ? O1 C1 C2 C3 -173.2(2) . . . . ? O2 C1 C2 C3 8.2(3) . . . . ? O1 C1 C2 C7 11.8(3) . . . . ? O2 C1 C2 C7 -166.9(2) . . . . ? C7 C2 C3 C4 1.3(4) . . . . ? C1 C2 C3 C4 -173.7(2) . . . . ? C2 C3 C4 C5 -2.8(4) . . . . ? C2 C3 C4 C8 171.8(2) . . . . ? C3 C4 C5 C6 2.6(4) . . . . ? C8 C4 C5 C6 -172.1(2) . . . . ? C9 O5 C6 C5 -163.5(3) . . . . ? C9 O5 C6 C7 13.8(4) . . . . ? C4 C5 C6 O5 176.7(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? O5 C6 C7 C2 -178.0(2) . . . . ? C5 C6 C7 C2 -0.8(4) . . . . ? C3 C2 C7 C6 0.5(4) . . . . ? C1 C2 C7 C6 175.6(2) . . . . ? Cu2 O4 C8 O3 21.2(4) 6_566 . . . ? Cu2 O4 C8 C4 -161.78(16) 6_566 . . . ? C5 C4 C8 O3 179.0(2) . . . . ? C3 C4 C8 O3 4.3(4) . . . . ? C5 C4 C8 O4 1.7(4) . . . . ? C3 C4 C8 O4 -173.0(2) . . . . ? C12 N1 C10 C11 0.2(3) . . . . ? Cu1 N1 C10 C11 169.1(2) . . . . ? N1 C10 C11 N2 0.2(4) . . . . ? C12 N2 C11 C10 -0.5(4) . . . . ? C13 N2 C11 C10 -174.0(3) . . . . ? C10 N1 C12 N2 -0.5(3) . . . . ? Cu1 N1 C12 N2 -169.61(18) . . . . ? C11 N2 C12 N1 0.6(3) . . . . ? C13 N2 C12 N1 174.2(3) . . . . ? C12 N2 C13 C13 -94.3(4) . . . 3_655 ? C11 N2 C13 C13 78.0(4) . . . 3_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H1W O3 0.85 1.85 2.661(2) 158.4 8_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.357 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 943589' ####################################################################### # # 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_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H44 Cu2 N8 O11' _chemical_formula_weight 1011.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.703(2) _cell_length_b 9.703(2) _cell_length_c 13.090(3) _cell_angle_alpha 80.909(2) _cell_angle_beta 77.613(2) _cell_angle_gamma 62.896(2) _cell_volume 1069.0(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2277 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.30 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.069 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7626 _exptl_absorpt_correction_T_max 0.8316 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8188 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3952 _reflns_number_gt 3131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0543P)^2^+0.4882P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3952 _refine_ls_number_parameters 308 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.67900(4) 0.84541(4) 0.60455(3) 0.02637(13) Uani 1 1 d . . . O1 O 0.8622(2) 0.6314(2) 0.62336(16) 0.0322(5) Uani 1 1 d . . . O2 O 0.8614(3) 0.7688(2) 0.74404(19) 0.0427(6) Uani 1 1 d . . . O3 O 1.4196(2) 0.2090(3) 0.51826(16) 0.0372(5) Uani 1 1 d . . . O4 O 1.5396(2) 0.0601(2) 0.65100(16) 0.0306(5) Uani 1 1 d . . . O5 O 1.2253(3) 0.3679(3) 0.96984(18) 0.0528(7) Uani 1 1 d U . . O6 O 0.4128(15) 0.5417(19) 0.4865(13) 0.238(7) Uani 0.50 1 d PU . . H1W H 0.4533 0.6036 0.4851 0.357 Uiso 0.50 1 d PR . . H2W H 0.4135 0.4528 0.4948 0.357 Uiso 0.50 1 d PR . . N1 N 0.5356(3) 0.7768(3) 0.70720(19) 0.0285(6) Uani 1 1 d . . . N2 N 0.3264(3) 0.7779(3) 0.8129(2) 0.0343(6) Uani 1 1 d . . . N3 N 0.0290(3) 0.8896(3) 1.38192(19) 0.0327(6) Uani 1 1 d . . . N4 N -0.1806(3) 0.9050(3) 1.49313(18) 0.0293(6) Uani 1 1 d . . . C1 C 0.9178(3) 0.6482(3) 0.6974(2) 0.0271(7) Uani 1 1 d . . . C2 C 1.0628(3) 0.5136(3) 0.7303(2) 0.0252(6) Uani 1 1 d . . . C3 C 1.1750(3) 0.4102(3) 0.6582(2) 0.0257(6) Uani 1 1 d . . . H3 H 1.1599 0.4209 0.5891 0.031 Uiso 1 1 calc R . . C4 C 1.3103(3) 0.2904(3) 0.6908(2) 0.0247(6) Uani 1 1 d . . . C5 C 1.3320(3) 0.2722(3) 0.7945(2) 0.0284(7) Uani 1 1 d U . . H5 H 1.4221 0.1920 0.8159 0.034 Uiso 1 1 calc R . . C6 C 1.2184(3) 0.3747(4) 0.8660(2) 0.0303(7) Uani 1 1 d U . . C7 C 1.0849(3) 0.4966(3) 0.8330(2) 0.0299(7) Uani 1 1 d U . . H7 H 1.0104 0.5668 0.8804 0.036 Uiso 1 1 calc R . . C8 C 1.4319(3) 0.1781(3) 0.6122(2) 0.0246(6) Uani 1 1 d . . . C9 C 1.3669(4) 0.2653(5) 1.0072(3) 0.0535(10) Uani 1 1 d U . . H9A H 1.3902 0.1603 0.9980 0.080 Uiso 1 1 calc R . . H9B H 1.3557 0.2777 1.0803 0.080 Uiso 1 1 calc R . . H9C H 1.4508 0.2884 0.9687 0.080 Uiso 1 1 calc R . . C10 C 0.4010(3) 0.8616(4) 0.7627(2) 0.0319(7) Uani 1 1 d . . . H10 H 0.3619 0.9680 0.7666 0.038 Uiso 1 1 calc R . . C11 C 0.5480(5) 0.6303(4) 0.7237(4) 0.0702(14) Uani 1 1 d . . . H11 H 0.6322 0.5431 0.6949 0.084 Uiso 1 1 calc R . . C12 C 0.4191(5) 0.6307(5) 0.7885(4) 0.0764(16) Uani 1 1 d . . . H12 H 0.3985 0.5453 0.8117 0.092 Uiso 1 1 calc R . . C13 C 0.1717(4) 0.8386(4) 0.8799(2) 0.0393(8) Uani 1 1 d . . . H13A H 0.1169 0.7798 0.8717 0.047 Uiso 1 1 calc R . . H13B H 0.1110 0.9457 0.8564 0.047 Uiso 1 1 calc R . . C14 C 0.1807(3) 0.8308(4) 0.9942(2) 0.0317(7) Uani 1 1 d . . . C15 C 0.2207(4) 0.9320(4) 1.0303(3) 0.0374(8) Uani 1 1 d . . . H15 H 0.2447 1.0033 0.9831 0.045 Uiso 1 1 calc R . . C16 C 0.2256(4) 0.9289(4) 1.1357(3) 0.0382(8) Uani 1 1 d . . . H16 H 0.2536 0.9974 1.1585 0.046 Uiso 1 1 calc R . . C17 C 0.1893(3) 0.8249(4) 1.2068(2) 0.0329(7) Uani 1 1 d . . . C18 C 0.1476(4) 0.7254(4) 1.1720(3) 0.0453(9) Uani 1 1 d . . . H18 H 0.1207 0.6563 1.2196 0.054 Uiso 1 1 calc R . . C19 C 0.1453(4) 0.7270(4) 1.0659(3) 0.0445(9) Uani 1 1 d . . . H19 H 0.1194 0.6570 1.0431 0.053 Uiso 1 1 calc R . . C20 C 0.1891(4) 0.8254(5) 1.3225(2) 0.0408(8) Uani 1 1 d . . . H20A H 0.2478 0.7201 1.3501 0.049 Uiso 1 1 calc R . . H20B H 0.2411 0.8866 1.3314 0.049 Uiso 1 1 calc R . . C21 C -0.0781(4) 1.0416(4) 1.3774(2) 0.0370(8) Uani 1 1 d . . . H21 H -0.0646 1.1229 1.3358 0.044 Uiso 1 1 calc R . . C22 C -0.2076(4) 1.0505(4) 1.4453(2) 0.0348(7) Uani 1 1 d . . . H22 H -0.3004 1.1405 1.4579 0.042 Uiso 1 1 calc R . . C23 C -0.0369(4) 0.8115(4) 1.4516(2) 0.0333(7) Uani 1 1 d . . . H23 H 0.0122 0.7052 1.4686 0.040 Uiso 1 1 calc 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 Cu1 0.0195(2) 0.0243(2) 0.0245(2) -0.00320(14) 0.00287(14) -0.00261(15) O1 0.0218(10) 0.0314(12) 0.0317(12) -0.0035(10) -0.0019(9) -0.0022(9) O2 0.0370(13) 0.0235(12) 0.0510(15) -0.0106(11) -0.0054(11) 0.0028(10) O3 0.0308(12) 0.0428(13) 0.0258(12) -0.0102(10) -0.0023(9) -0.0041(10) O4 0.0234(10) 0.0250(11) 0.0290(11) -0.0052(9) 0.0021(9) 0.0001(9) O5 0.0356(13) 0.0672(17) 0.0283(13) -0.0169(12) -0.0093(10) 0.0068(12) O6 0.249(11) 0.213(10) 0.249(10) 0.011(8) -0.032(8) -0.111(8) N1 0.0234(13) 0.0272(13) 0.0263(13) -0.0040(11) 0.0017(10) -0.0055(11) N2 0.0324(14) 0.0408(16) 0.0270(14) -0.0057(12) 0.0068(11) -0.0177(13) N3 0.0259(13) 0.0462(16) 0.0230(14) -0.0076(12) 0.0049(11) -0.0152(12) N4 0.0248(13) 0.0330(14) 0.0233(13) -0.0048(11) 0.0021(10) -0.0086(11) C1 0.0208(14) 0.0218(15) 0.0277(16) -0.0005(12) 0.0048(12) -0.0039(12) C2 0.0186(14) 0.0198(14) 0.0305(17) -0.0045(12) 0.0004(12) -0.0037(12) C3 0.0239(15) 0.0225(15) 0.0247(15) -0.0017(12) -0.0020(12) -0.0057(12) C4 0.0213(14) 0.0234(15) 0.0261(16) -0.0056(12) 0.0016(12) -0.0082(12) C5 0.0209(14) 0.0265(15) 0.0287(16) -0.0038(12) -0.0030(12) -0.0025(12) C6 0.0274(15) 0.0324(16) 0.0243(15) -0.0075(13) -0.0044(12) -0.0056(13) C7 0.0251(15) 0.0274(16) 0.0310(17) -0.0126(13) 0.0046(12) -0.0067(13) C8 0.0208(14) 0.0237(15) 0.0269(16) -0.0051(12) -0.0010(12) -0.0079(12) C9 0.042(2) 0.065(2) 0.035(2) -0.0078(18) -0.0165(16) -0.0012(18) C10 0.0295(16) 0.0278(16) 0.0292(17) -0.0026(13) 0.0007(13) -0.0068(14) C11 0.056(3) 0.031(2) 0.098(4) -0.019(2) 0.039(2) -0.0150(19) C12 0.073(3) 0.035(2) 0.105(4) -0.018(2) 0.041(3) -0.030(2) C13 0.0250(16) 0.058(2) 0.0319(18) -0.0074(16) 0.0045(13) -0.0178(16) C14 0.0245(15) 0.0388(18) 0.0273(17) -0.0077(14) 0.0057(13) -0.0124(14) C15 0.0356(18) 0.043(2) 0.0338(19) -0.0027(15) 0.0051(14) -0.0216(16) C16 0.0322(17) 0.044(2) 0.0389(19) -0.0144(16) 0.0050(15) -0.0186(16) C17 0.0230(15) 0.0419(19) 0.0285(17) -0.0089(14) 0.0073(13) -0.0126(14) C18 0.060(2) 0.049(2) 0.0331(19) 0.0026(16) 0.0003(17) -0.0349(19) C19 0.060(2) 0.048(2) 0.036(2) -0.0073(17) 0.0020(17) -0.0356(19) C20 0.0264(16) 0.060(2) 0.0298(18) -0.0121(16) 0.0043(14) -0.0150(16) C21 0.0423(19) 0.0409(19) 0.0268(17) 0.0005(14) 0.0008(14) -0.0211(16) C22 0.0318(17) 0.0352(18) 0.0289(17) -0.0037(14) -0.0017(14) -0.0084(14) C23 0.0299(16) 0.0360(18) 0.0268(17) -0.0051(14) 0.0018(13) -0.0102(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.979(2) 1_654 ? Cu1 N1 1.986(2) . ? Cu1 O4 2.004(2) 1_465 ? Cu1 O1 2.048(2) . ? Cu1 O3 2.273(2) 2_766 ? O1 C1 1.269(4) . ? O2 C1 1.241(3) . ? O3 C8 1.237(3) . ? O3 Cu1 2.273(2) 2_766 ? O4 C8 1.271(3) . ? O4 Cu1 2.004(2) 1_645 ? O5 C6 1.365(4) . ? O5 C9 1.417(4) . ? O6 O6 1.60(3) 2_666 ? O6 H1W 0.8507 . ? O6 H2W 0.8495 . ? N1 C10 1.308(4) . ? N1 C11 1.357(4) . ? N2 C10 1.333(4) . ? N2 C12 1.343(5) . ? N2 C13 1.470(4) . ? N3 C23 1.338(4) . ? N3 C21 1.364(4) . ? N3 C20 1.470(4) . ? N4 C23 1.320(4) . ? N4 C22 1.381(4) . ? N4 Cu1 1.979(2) 1_456 ? C1 C2 1.510(4) . ? C2 C7 1.378(4) . ? C2 C3 1.395(4) . ? C3 C4 1.396(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 C8 1.517(4) . ? C5 C6 1.390(4) . ? C5 H5 0.9300 . ? C6 C7 1.395(4) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 C12 1.351(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.506(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.375(5) . ? C14 C15 1.383(4) . ? C15 C16 1.385(4) . ? C15 H15 0.9300 . ? C16 C17 1.377(5) . ? C16 H16 0.9300 . ? C17 C18 1.370(5) . ? C17 C20 1.514(4) . ? C18 C19 1.391(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.350(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N1 175.11(10) 1_654 . ? N4 Cu1 O4 95.95(9) 1_654 1_465 ? N1 Cu1 O4 86.99(9) . 1_465 ? N4 Cu1 O1 89.18(9) 1_654 . ? N1 Cu1 O1 90.16(9) . . ? O4 Cu1 O1 150.43(9) 1_465 . ? N4 Cu1 O3 90.50(9) 1_654 2_766 ? N1 Cu1 O3 84.80(9) . 2_766 ? O4 Cu1 O3 110.63(8) 1_465 2_766 ? O1 Cu1 O3 98.39(8) . 2_766 ? C1 O1 Cu1 102.62(17) . . ? C8 O3 Cu1 139.9(2) . 2_766 ? C8 O4 Cu1 133.26(19) . 1_645 ? C6 O5 C9 119.1(2) . . ? O6 O6 H1W 66.2 2_666 . ? O6 O6 H2W 87.6 2_666 . ? H1W O6 H2W 153.7 . . ? C10 N1 C11 104.9(3) . . ? C10 N1 Cu1 128.7(2) . . ? C11 N1 Cu1 125.9(2) . . ? C10 N2 C12 106.4(3) . . ? C10 N2 C13 125.8(3) . . ? C12 N2 C13 127.8(3) . . ? C23 N3 C21 107.7(3) . . ? C23 N3 C20 126.6(3) . . ? C21 N3 C20 125.7(3) . . ? C23 N4 C22 105.6(3) . . ? C23 N4 Cu1 126.0(2) . 1_456 ? C22 N4 Cu1 128.4(2) . 1_456 ? O2 C1 O1 124.3(3) . . ? O2 C1 C2 117.7(3) . . ? O1 C1 C2 118.1(2) . . ? C7 C2 C3 120.2(3) . . ? C7 C2 C1 118.7(2) . . ? C3 C2 C1 121.1(3) . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 C8 120.3(2) . . ? C3 C4 C8 119.2(3) . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? O5 C6 C5 125.2(3) . . ? O5 C6 C7 114.9(3) . . ? C5 C6 C7 119.9(3) . . ? C2 C7 C6 120.4(3) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O3 C8 O4 126.3(3) . . ? O3 C8 C4 118.5(2) . . ? O4 C8 C4 115.2(3) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 112.3(3) . . ? N1 C10 H10 123.8 . . ? N2 C10 H10 123.8 . . ? C12 C11 N1 109.5(3) . . ? C12 C11 H11 125.3 . . ? N1 C11 H11 125.3 . . ? N2 C12 C11 106.9(3) . . ? N2 C12 H12 126.5 . . ? C11 C12 H12 126.5 . . ? N2 C13 C14 113.3(3) . . ? N2 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? N2 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C19 C14 C15 118.2(3) . . ? C19 C14 C13 121.5(3) . . ? C15 C14 C13 120.3(3) . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 119.1(3) . . ? C18 C17 C20 120.6(3) . . ? C16 C17 C20 120.2(3) . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 120.9(3) . . ? C14 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? N3 C20 C17 111.8(3) . . ? N3 C20 H20A 109.3 . . ? C17 C20 H20A 109.3 . . ? N3 C20 H20B 109.3 . . ? C17 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C22 C21 N3 106.4(3) . . ? C22 C21 H21 126.8 . . ? N3 C21 H21 126.8 . . ? C21 C22 N4 109.3(3) . . ? C21 C22 H22 125.4 . . ? N4 C22 H22 125.4 . . ? N4 C23 N3 111.1(3) . . ? N4 C23 H23 124.5 . . ? N3 C23 H23 124.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 O1 C1 94.31(19) 1_654 . . . ? N1 Cu1 O1 C1 -90.53(19) . . . . ? O4 Cu1 O1 C1 -6.4(3) 1_465 . . . ? O3 Cu1 O1 C1 -175.30(17) 2_766 . . . ? N4 Cu1 N1 C10 -119.5(11) 1_654 . . . ? O4 Cu1 N1 C10 7.7(3) 1_465 . . . ? O1 Cu1 N1 C10 158.2(3) . . . . ? O3 Cu1 N1 C10 -103.4(3) 2_766 . . . ? N4 Cu1 N1 C11 50.8(13) 1_654 . . . ? O4 Cu1 N1 C11 178.0(3) 1_465 . . . ? O1 Cu1 N1 C11 -31.4(3) . . . . ? O3 Cu1 N1 C11 67.0(3) 2_766 . . . ? Cu1 O1 C1 O2 2.3(3) . . . . ? Cu1 O1 C1 C2 -177.0(2) . . . . ? O2 C1 C2 C7 29.9(4) . . . . ? O1 C1 C2 C7 -150.7(3) . . . . ? O2 C1 C2 C3 -148.4(3) . . . . ? O1 C1 C2 C3 31.0(4) . . . . ? C7 C2 C3 C4 -0.6(4) . . . . ? C1 C2 C3 C4 177.7(3) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 C8 179.9(2) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C8 C4 C5 C6 -179.0(3) . . . . ? C9 O5 C6 C5 10.1(5) . . . . ? C9 O5 C6 C7 -169.5(3) . . . . ? C4 C5 C6 O5 179.2(3) . . . . ? C4 C5 C6 C7 -1.2(5) . . . . ? C3 C2 C7 C6 -0.9(5) . . . . ? C1 C2 C7 C6 -179.3(3) . . . . ? O5 C6 C7 C2 -178.5(3) . . . . ? C5 C6 C7 C2 1.9(5) . . . . ? Cu1 O3 C8 O4 85.1(4) 2_766 . . . ? Cu1 O3 C8 C4 -95.9(3) 2_766 . . . ? Cu1 O4 C8 O3 -26.8(5) 1_645 . . . ? Cu1 O4 C8 C4 154.23(19) 1_645 . . . ? C5 C4 C8 O3 -170.6(3) . . . . ? C3 C4 C8 O3 10.7(4) . . . . ? C5 C4 C8 O4 8.6(4) . . . . ? C3 C4 C8 O4 -170.2(3) . . . . ? C11 N1 C10 N2 -0.5(4) . . . . ? Cu1 N1 C10 N2 171.4(2) . . . . ? C12 N2 C10 N1 0.3(4) . . . . ? C13 N2 C10 N1 -178.7(3) . . . . ? C10 N1 C11 C12 0.5(5) . . . . ? Cu1 N1 C11 C12 -171.7(3) . . . . ? C10 N2 C12 C11 0.0(5) . . . . ? C13 N2 C12 C11 179.0(4) . . . . ? N1 C11 C12 N2 -0.3(6) . . . . ? C10 N2 C13 C14 -93.5(4) . . . . ? C12 N2 C13 C14 87.7(5) . . . . ? N2 C13 C14 C19 -108.6(4) . . . . ? N2 C13 C14 C15 73.3(4) . . . . ? C19 C14 C15 C16 0.2(5) . . . . ? C13 C14 C15 C16 178.4(3) . . . . ? C14 C15 C16 C17 -0.5(5) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C15 C16 C17 C20 -177.8(3) . . . . ? C16 C17 C18 C19 1.4(5) . . . . ? C20 C17 C18 C19 178.8(3) . . . . ? C15 C14 C19 C18 0.8(5) . . . . ? C13 C14 C19 C18 -177.3(3) . . . . ? C17 C18 C19 C14 -1.7(6) . . . . ? C23 N3 C20 C17 111.0(4) . . . . ? C21 N3 C20 C17 -70.7(4) . . . . ? C18 C17 C20 N3 -70.3(4) . . . . ? C16 C17 C20 N3 107.1(3) . . . . ? C23 N3 C21 C22 -0.2(4) . . . . ? C20 N3 C21 C22 -178.8(3) . . . . ? N3 C21 C22 N4 0.8(4) . . . . ? C23 N4 C22 C21 -1.1(4) . . . . ? Cu1 N4 C22 C21 176.7(2) 1_456 . . . ? C22 N4 C23 N3 1.0(3) . . . . ? Cu1 N4 C23 N3 -176.90(19) 1_456 . . . ? C21 N3 C23 N4 -0.5(4) . . . . ? C20 N3 C23 N4 178.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H2W O3 0.85 2.31 3.161(17) 179.0 1_455 O6 H1W O3 0.85 2.61 3.463(16) 179.3 2_766 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.344 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 943590' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H28 Cu N4 O7' _chemical_formula_weight 584.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 10.809(10) _cell_length_b 10.847(10) _cell_length_c 12.549(11) _cell_angle_alpha 93.404(11) _cell_angle_beta 90.140(11) _cell_angle_gamma 118.890(10) _cell_volume 1285.0(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1221 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 20.52 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8476 _exptl_absorpt_correction_T_max 0.9047 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9681 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0937 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4749 _reflns_number_gt 3069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0438P)^2^+0.1893P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4749 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.64668(5) 0.62073(5) 0.75472(4) 0.03154(18) Uani 1 1 d . . . O1 O 0.4789(3) 0.6301(3) 0.7166(2) 0.0421(8) Uani 1 1 d . . . O2 O 0.3682(3) 0.6058(4) 0.8693(3) 0.0559(10) Uani 1 1 d . . . O3 O -0.1741(3) 0.6373(3) 0.7133(2) 0.0354(7) Uani 1 1 d . . . O4 O -0.0944(3) 0.6014(4) 0.8658(3) 0.0512(9) Uani 1 1 d . . . O5 O 0.2003(3) 0.7138(3) 0.4472(2) 0.0503(9) Uani 1 1 d . . . O6 O 0.6449(4) 0.5586(4) 0.9521(3) 0.0793(12) Uani 1 1 d . . . H1W H 0.6950 0.5365 0.9907 0.119 Uiso 1 1 d R . . H2W H 0.5637 0.4864 0.9425 0.119 Uiso 1 1 d R . . O7 O 0.7792(5) 0.3371(4) 0.9608(3) 0.1042(16) Uani 1 1 d . . . H3W H 0.8536 0.3314 0.9481 0.156 Uiso 1 1 d R . . H4W H 0.8044 0.4214 0.9465 0.156 Uiso 1 1 d R . . N1 N 0.5558(3) 0.4152(3) 0.7107(3) 0.0313(8) Uani 1 1 d . . . N2 N 0.5390(4) 0.2014(3) 0.7051(3) 0.0312(8) Uani 1 1 d . . . N3 N 0.2299(4) 0.0251(3) 1.0444(3) 0.0334(9) Uani 1 1 d . . . N4 N 0.2573(3) 0.1852(3) 1.1756(3) 0.0318(8) Uani 1 1 d . . . C1 C 0.3777(4) 0.6217(4) 0.7714(4) 0.0330(11) Uani 1 1 d . . . C2 C 0.2648(4) 0.6352(4) 0.7120(3) 0.0281(10) Uani 1 1 d . . . C3 C 0.2792(4) 0.6665(4) 0.6063(3) 0.0331(10) Uani 1 1 d . . . H3 H 0.3585 0.6765 0.5706 0.040 Uiso 1 1 calc R . . C4 C 0.1761(4) 0.6832(4) 0.5523(3) 0.0321(10) Uani 1 1 d . . . C5 C 0.0587(4) 0.6691(4) 0.6049(3) 0.0323(10) Uani 1 1 d . . . H5 H -0.0108 0.6794 0.5690 0.039 Uiso 1 1 calc R . . C6 C 0.0444(4) 0.6392(4) 0.7121(3) 0.0261(9) Uani 1 1 d . . . C7 C 0.1460(4) 0.6216(4) 0.7648(3) 0.0302(9) Uani 1 1 d . . . H7 H 0.1354 0.6006 0.8361 0.036 Uiso 1 1 calc R . . C8 C -0.0842(4) 0.6240(4) 0.7694(4) 0.0336(11) Uani 1 1 d . . . C9 C 0.0924(5) 0.7202(5) 0.3872(4) 0.0493(13) Uani 1 1 d . . . H9A H 0.0055 0.6333 0.3908 0.074 Uiso 1 1 calc R . . H9B H 0.1188 0.7342 0.3141 0.074 Uiso 1 1 calc R . . H9C H 0.0799 0.7972 0.4161 0.074 Uiso 1 1 calc R . . C10 C 0.4575(4) 0.3286(4) 0.6298(3) 0.0294(10) Uani 1 1 d . . . C11 C 0.3755(5) 0.3568(5) 0.5607(3) 0.0386(11) Uani 1 1 d . . . H11 H 0.3796 0.4446 0.5633 0.046 Uiso 1 1 calc R . . C12 C 0.2874(5) 0.2489(5) 0.4879(4) 0.0458(12) Uani 1 1 d . . . H12 H 0.2303 0.2642 0.4410 0.055 Uiso 1 1 calc R . . C13 C 0.2819(5) 0.1192(5) 0.4830(4) 0.0544(14) Uani 1 1 d . . . H13 H 0.2223 0.0501 0.4317 0.065 Uiso 1 1 calc R . . C14 C 0.3610(5) 0.0881(5) 0.5509(3) 0.0445(12) Uani 1 1 d . . . H14 H 0.3565 0.0002 0.5473 0.053 Uiso 1 1 calc R . . C15 C 0.4481(4) 0.1955(4) 0.6252(3) 0.0310(10) Uani 1 1 d . . . C16 C 0.5986(4) 0.3333(4) 0.7520(3) 0.0340(10) Uani 1 1 d . . . H16 H 0.6644 0.3637 0.8088 0.041 Uiso 1 1 calc R . . C17 C 0.5521(5) 0.0840(4) 0.7434(3) 0.0380(11) Uani 1 1 d . . . H17A H 0.6347 0.1204 0.7912 0.046 Uiso 1 1 calc R . . H17B H 0.5659 0.0320 0.6833 0.046 Uiso 1 1 calc R . . C18 C 0.4217(5) -0.0155(4) 0.8019(3) 0.0384(11) Uani 1 1 d . . . H18A H 0.3401 -0.0557 0.7528 0.046 Uiso 1 1 calc R . . H18B H 0.4343 -0.0923 0.8256 0.046 Uiso 1 1 calc R . . C19 C 0.3936(5) 0.0585(4) 0.8978(3) 0.0387(11) Uani 1 1 d . . . H19A H 0.4708 0.0906 0.9504 0.046 Uiso 1 1 calc R . . H19B H 0.3894 0.1405 0.8756 0.046 Uiso 1 1 calc R . . C20 C 0.2564(5) -0.0392(5) 0.9478(3) 0.0420(12) Uani 1 1 d . . . H20A H 0.1790 -0.0665 0.8962 0.050 Uiso 1 1 calc R . . H20B H 0.2586 -0.1240 0.9652 0.050 Uiso 1 1 calc R . . C21 C 0.3122(4) 0.1552(4) 1.0907(3) 0.0324(10) Uani 1 1 d . . . H21 H 0.3997 0.2181 1.0654 0.039 Uiso 1 1 calc R . . C22 C 0.1272(4) 0.0625(4) 1.1871(3) 0.0286(10) Uani 1 1 d . . . C23 C 0.0237(4) 0.0298(5) 1.2614(3) 0.0378(11) Uani 1 1 d . . . H23 H 0.0329 0.0950 1.3166 0.045 Uiso 1 1 calc R . . C24 C -0.0935(5) -0.1024(5) 1.2514(4) 0.0469(13) Uani 1 1 d . . . H24 H -0.1640 -0.1263 1.3010 0.056 Uiso 1 1 calc R . . C25 C -0.1092(5) -0.2014(5) 1.1685(4) 0.0589(15) Uani 1 1 d . . . H25 H -0.1894 -0.2899 1.1642 0.071 Uiso 1 1 calc R . . C26 C -0.0080(5) -0.1701(5) 1.0932(4) 0.0496(13) Uani 1 1 d . . . H26 H -0.0181 -0.2346 1.0371 0.059 Uiso 1 1 calc R . . C27 C 0.1101(4) -0.0373(4) 1.1052(3) 0.0351(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0194(3) 0.0291(3) 0.0463(4) -0.0069(2) -0.0012(2) 0.0130(2) O1 0.0249(16) 0.052(2) 0.056(2) -0.0131(16) -0.0054(15) 0.0254(15) O2 0.0338(19) 0.080(3) 0.057(2) 0.024(2) 0.0000(17) 0.0274(19) O3 0.0241(16) 0.0391(18) 0.0476(19) -0.0016(14) 0.0000(14) 0.0194(14) O4 0.042(2) 0.074(2) 0.043(2) 0.0070(18) 0.0118(16) 0.0323(19) O5 0.046(2) 0.072(2) 0.0375(19) 0.0150(17) 0.0122(16) 0.0315(19) O6 0.078(3) 0.082(3) 0.085(3) 0.013(2) 0.000(2) 0.044(2) O7 0.144(4) 0.091(3) 0.090(3) 0.007(3) -0.030(3) 0.067(3) N1 0.0288(19) 0.028(2) 0.037(2) -0.0003(17) 0.0012(17) 0.0143(17) N2 0.035(2) 0.029(2) 0.032(2) 0.0012(16) 0.0036(17) 0.0176(17) N3 0.033(2) 0.0255(19) 0.034(2) -0.0045(16) 0.0031(17) 0.0085(17) N4 0.0210(18) 0.029(2) 0.038(2) -0.0047(16) 0.0039(16) 0.0074(16) C1 0.024(2) 0.022(2) 0.052(3) -0.001(2) -0.003(2) 0.0108(19) C2 0.023(2) 0.025(2) 0.040(3) -0.0009(19) 0.0028(19) 0.0152(19) C3 0.019(2) 0.031(2) 0.048(3) -0.001(2) 0.006(2) 0.0118(19) C4 0.028(2) 0.033(2) 0.035(3) 0.001(2) 0.003(2) 0.015(2) C5 0.022(2) 0.033(2) 0.046(3) 0.003(2) 0.000(2) 0.017(2) C6 0.021(2) 0.024(2) 0.035(3) -0.0038(18) 0.0014(18) 0.0121(18) C7 0.023(2) 0.031(2) 0.034(2) 0.0003(19) -0.0003(18) 0.0122(18) C8 0.021(2) 0.030(3) 0.046(3) -0.005(2) 0.002(2) 0.011(2) C9 0.049(3) 0.057(3) 0.040(3) 0.009(2) -0.005(2) 0.025(3) C10 0.025(2) 0.026(2) 0.029(2) -0.0030(19) 0.0050(19) 0.0064(19) C11 0.040(3) 0.034(3) 0.038(3) 0.003(2) 0.001(2) 0.015(2) C12 0.051(3) 0.042(3) 0.035(3) 0.002(2) -0.008(2) 0.016(3) C13 0.064(4) 0.040(3) 0.039(3) -0.010(2) -0.014(3) 0.011(3) C14 0.059(3) 0.033(3) 0.035(3) -0.003(2) 0.002(2) 0.018(2) C15 0.029(2) 0.030(2) 0.029(2) -0.0003(19) 0.0033(19) 0.011(2) C16 0.028(2) 0.032(3) 0.039(3) -0.004(2) -0.003(2) 0.013(2) C17 0.051(3) 0.035(3) 0.038(3) 0.004(2) 0.006(2) 0.029(2) C18 0.051(3) 0.031(3) 0.036(3) 0.002(2) 0.009(2) 0.022(2) C19 0.049(3) 0.034(3) 0.035(3) 0.001(2) 0.009(2) 0.022(2) C20 0.045(3) 0.036(3) 0.038(3) -0.002(2) 0.009(2) 0.015(2) C21 0.025(2) 0.026(2) 0.042(3) 0.000(2) 0.006(2) 0.009(2) C22 0.026(2) 0.026(2) 0.030(2) 0.0003(19) -0.0022(19) 0.0108(19) C23 0.033(2) 0.040(3) 0.037(3) -0.002(2) 0.001(2) 0.015(2) C24 0.033(3) 0.048(3) 0.045(3) 0.007(2) 0.009(2) 0.007(2) C25 0.041(3) 0.040(3) 0.062(4) 0.002(3) 0.011(3) -0.007(2) C26 0.044(3) 0.034(3) 0.044(3) -0.008(2) 0.006(2) -0.001(2) C27 0.031(2) 0.029(2) 0.036(3) 0.003(2) 0.006(2) 0.007(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 Cu1 O1 1.925(3) . ? Cu1 O3 1.933(3) 1_655 ? Cu1 N4 1.985(4) 2_667 ? Cu1 N1 1.994(4) . ? Cu1 O6 2.604(4) . ? O1 C1 1.262(5) . ? O2 C1 1.248(5) . ? O3 C8 1.267(5) . ? O3 Cu1 1.933(3) 1_455 ? O4 C8 1.243(5) . ? O5 C4 1.374(5) . ? O5 C9 1.419(5) . ? O6 H1W 0.8501 . ? O6 H2W 0.8500 . ? O7 H3W 0.8500 . ? O7 H4W 0.8500 . ? N1 C16 1.312(5) . ? N1 C10 1.400(5) . ? N2 C16 1.348(5) . ? N2 C15 1.379(5) . ? N2 C17 1.456(5) . ? N3 C21 1.344(5) . ? N3 C27 1.392(5) . ? N3 C20 1.460(5) . ? N4 C21 1.320(5) . ? N4 C22 1.408(5) . ? N4 Cu1 1.985(4) 2_667 ? C1 C2 1.498(6) . ? C2 C3 1.379(6) . ? C2 C7 1.394(5) . ? C3 C4 1.393(6) . ? C3 H3 0.9300 . ? C4 C5 1.377(5) . ? C5 C6 1.395(5) . ? C5 H5 0.9300 . ? C6 C7 1.376(5) . ? C6 C8 1.508(5) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.386(6) . ? C10 C15 1.395(6) . ? C11 C12 1.379(6) . ? C11 H11 0.9300 . ? C12 C13 1.377(6) . ? C12 H12 0.9300 . ? C13 C14 1.371(6) . ? C13 H13 0.9300 . ? C14 C15 1.386(6) . ? C14 H14 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.523(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.519(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.510(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21 0.9300 . ? C22 C23 1.381(6) . ? C22 C27 1.391(5) . ? C23 C24 1.378(6) . ? C23 H23 0.9300 . ? C24 C25 1.398(6) . ? C24 H24 0.9300 . ? C25 C26 1.375(6) . ? C25 H25 0.9300 . ? C26 C27 1.387(6) . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 148.58(13) . 1_655 ? O1 Cu1 N4 93.51(13) . 2_667 ? O3 Cu1 N4 91.08(13) 1_655 2_667 ? O1 Cu1 N1 92.26(14) . . ? O3 Cu1 N1 88.60(13) 1_655 . ? N4 Cu1 N1 169.44(14) 2_667 . ? O1 Cu1 O6 111.43(13) . . ? O3 Cu1 O6 99.99(12) 1_655 . ? N4 Cu1 O6 81.05(14) 2_667 . ? N1 Cu1 O6 88.61(13) . . ? C1 O1 Cu1 131.7(3) . . ? C8 O3 Cu1 128.6(3) . 1_455 ? C4 O5 C9 117.7(3) . . ? Cu1 O6 H1W 135.4 . . ? Cu1 O6 H2W 91.7 . . ? H1W O6 H2W 107.9 . . ? H3W O7 H4W 101.8 . . ? C16 N1 C10 104.3(3) . . ? C16 N1 Cu1 121.3(3) . . ? C10 N1 Cu1 134.0(3) . . ? C16 N2 C15 106.4(3) . . ? C16 N2 C17 125.7(4) . . ? C15 N2 C17 127.2(4) . . ? C21 N3 C27 106.4(3) . . ? C21 N3 C20 127.7(3) . . ? C27 N3 C20 125.8(3) . . ? C21 N4 C22 105.0(3) . . ? C21 N4 Cu1 119.5(3) . 2_667 ? C22 N4 Cu1 135.2(3) . 2_667 ? O2 C1 O1 124.6(4) . . ? O2 C1 C2 119.6(4) . . ? O1 C1 C2 115.8(4) . . ? C3 C2 C7 119.1(4) . . ? C3 C2 C1 120.9(4) . . ? C7 C2 C1 119.9(4) . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? O5 C4 C5 124.1(4) . . ? O5 C4 C3 116.1(4) . . ? C5 C4 C3 119.8(4) . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.2(4) . . ? C7 C6 C8 120.3(4) . . ? C5 C6 C8 119.5(4) . . ? C6 C7 C2 120.4(4) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? O4 C8 O3 125.1(4) . . ? O4 C8 C6 119.3(4) . . ? O3 C8 C6 115.7(4) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 120.4(4) . . ? C11 C10 N1 130.4(4) . . ? C15 C10 N1 109.2(4) . . ? C12 C11 C10 117.1(4) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? C13 C12 C11 121.7(5) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C14 C13 C12 122.4(4) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 116.1(4) . . ? C13 C14 H14 122.0 . . ? C15 C14 H14 122.0 . . ? N2 C15 C14 131.8(4) . . ? N2 C15 C10 105.8(4) . . ? C14 C15 C10 122.3(4) . . ? N1 C16 N2 114.2(4) . . ? N1 C16 H16 122.9 . . ? N2 C16 H16 122.9 . . ? N2 C17 C18 111.7(3) . . ? N2 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? N2 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 112.4(4) . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 111.1(4) . . ? C20 C19 H19A 109.4 . . ? C18 C19 H19A 109.4 . . ? C20 C19 H19B 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? N3 C20 C19 112.8(4) . . ? N3 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? N3 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? N4 C21 N3 113.7(4) . . ? N4 C21 H21 123.2 . . ? N3 C21 H21 123.2 . . ? C23 C22 C27 119.5(4) . . ? C23 C22 N4 131.9(4) . . ? C27 C22 N4 108.5(4) . . ? C24 C23 C22 118.1(4) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C23 C24 C25 121.6(4) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C26 C25 C24 121.0(4) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 116.6(4) . . ? C25 C26 H26 121.7 . . ? C27 C26 H26 121.7 . . ? C26 C27 N3 130.5(4) . . ? C26 C27 C22 123.1(4) . . ? N3 C27 C22 106.4(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 O3 Cu1 O1 C1 -173.8(3) 1_655 . . . ? N4 Cu1 O1 C1 -76.0(4) 2_667 . . . ? N1 Cu1 O1 C1 95.1(4) . . . . ? O6 Cu1 O1 C1 5.8(4) . . . . ? O1 Cu1 N1 C16 -154.8(3) . . . . ? O3 Cu1 N1 C16 56.7(3) 1_655 . . . ? N4 Cu1 N1 C16 -31.7(9) 2_667 . . . ? O6 Cu1 N1 C16 -43.4(3) . . . . ? O1 Cu1 N1 C10 34.6(4) . . . . ? O3 Cu1 N1 C10 -113.9(4) 1_655 . . . ? N4 Cu1 N1 C10 157.7(6) 2_667 . . . ? O6 Cu1 N1 C10 146.0(4) . . . . ? Cu1 O1 C1 O2 0.9(6) . . . . ? Cu1 O1 C1 C2 179.6(2) . . . . ? O2 C1 C2 C3 173.6(4) . . . . ? O1 C1 C2 C3 -5.1(5) . . . . ? O2 C1 C2 C7 -3.8(6) . . . . ? O1 C1 C2 C7 177.5(4) . . . . ? C7 C2 C3 C4 -0.6(6) . . . . ? C1 C2 C3 C4 -178.0(4) . . . . ? C9 O5 C4 C5 -5.1(6) . . . . ? C9 O5 C4 C3 174.9(4) . . . . ? C2 C3 C4 O5 -179.8(4) . . . . ? C2 C3 C4 C5 0.3(6) . . . . ? O5 C4 C5 C6 -179.4(4) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C4 C5 C6 C7 -1.1(6) . . . . ? C4 C5 C6 C8 179.9(4) . . . . ? C5 C6 C7 C2 0.8(6) . . . . ? C8 C6 C7 C2 179.8(4) . . . . ? C3 C2 C7 C6 0.1(6) . . . . ? C1 C2 C7 C6 177.5(4) . . . . ? Cu1 O3 C8 O4 -2.5(6) 1_455 . . . ? Cu1 O3 C8 C6 178.3(2) 1_455 . . . ? C7 C6 C8 O4 3.0(6) . . . . ? C5 C6 C8 O4 -178.0(4) . . . . ? C7 C6 C8 O3 -177.7(4) . . . . ? C5 C6 C8 O3 1.4(5) . . . . ? C16 N1 C10 C11 178.4(4) . . . . ? Cu1 N1 C10 C11 -9.9(7) . . . . ? C16 N1 C10 C15 -1.2(4) . . . . ? Cu1 N1 C10 C15 170.5(3) . . . . ? C15 C10 C11 C12 -0.8(6) . . . . ? N1 C10 C11 C12 179.7(4) . . . . ? C10 C11 C12 C13 -0.7(7) . . . . ? C11 C12 C13 C14 1.2(8) . . . . ? C12 C13 C14 C15 -0.2(7) . . . . ? C16 N2 C15 C14 179.0(4) . . . . ? C17 N2 C15 C14 -10.0(7) . . . . ? C16 N2 C15 C10 -0.7(4) . . . . ? C17 N2 C15 C10 170.3(4) . . . . ? C13 C14 C15 N2 179.0(4) . . . . ? C13 C14 C15 C10 -1.3(6) . . . . ? C11 C10 C15 N2 -178.4(4) . . . . ? N1 C10 C15 N2 1.2(4) . . . . ? C11 C10 C15 C14 1.8(6) . . . . ? N1 C10 C15 C14 -178.6(4) . . . . ? C10 N1 C16 N2 0.7(5) . . . . ? Cu1 N1 C16 N2 -172.3(3) . . . . ? C15 N2 C16 N1 0.0(5) . . . . ? C17 N2 C16 N1 -171.2(4) . . . . ? C16 N2 C17 C18 100.8(5) . . . . ? C15 N2 C17 C18 -68.6(5) . . . . ? N2 C17 C18 C19 -59.2(5) . . . . ? C17 C18 C19 C20 174.6(4) . . . . ? C21 N3 C20 C19 -0.6(6) . . . . ? C27 N3 C20 C19 177.6(4) . . . . ? C18 C19 C20 N3 176.3(4) . . . . ? C22 N4 C21 N3 0.8(5) . . . . ? Cu1 N4 C21 N3 -173.3(3) 2_667 . . . ? C27 N3 C21 N4 -0.8(5) . . . . ? C20 N3 C21 N4 177.6(4) . . . . ? C21 N4 C22 C23 179.2(4) . . . . ? Cu1 N4 C22 C23 -8.0(7) 2_667 . . . ? C21 N4 C22 C27 -0.5(4) . . . . ? Cu1 N4 C22 C27 172.3(3) 2_667 . . . ? C27 C22 C23 C24 0.2(6) . . . . ? N4 C22 C23 C24 -179.5(4) . . . . ? C22 C23 C24 C25 -0.3(7) . . . . ? C23 C24 C25 C26 -0.3(8) . . . . ? C24 C25 C26 C27 1.1(8) . . . . ? C25 C26 C27 N3 179.2(5) . . . . ? C25 C26 C27 C22 -1.2(7) . . . . ? C21 N3 C27 C26 -180.0(5) . . . . ? C20 N3 C27 C26 1.6(8) . . . . ? C21 N3 C27 C22 0.4(5) . . . . ? C20 N3 C27 C22 -178.0(4) . . . . ? C23 C22 C27 C26 0.6(7) . . . . ? N4 C22 C27 C26 -179.6(4) . . . . ? C23 C22 C27 N3 -179.8(4) . . . . ? N4 C22 C27 N3 0.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H4W O6 0.85 2.77 3.360(6) 128.3 . O7 H4W O4 0.85 2.05 2.852(6) 156.7 1_655 O6 H2W O6 0.85 2.47 3.037(8) 124.9 2_667 O6 H1W O2 0.85 2.29 2.908(5) 129.7 2_667 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.343 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 943591' ####################################################################### # # 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_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H46 Mn3 N4 O26' _chemical_formula_weight 1211.67 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.846(7) _cell_length_b 14.108(10) _cell_length_c 19.466(14) _cell_angle_alpha 97.416(8) _cell_angle_beta 104.173(8) _cell_angle_gamma 104.323(9) _cell_volume 2488(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2564 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 23.49 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1242 _exptl_absorpt_coefficient_mu 0.846 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7989 _exptl_absorpt_correction_T_max 0.8851 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16526 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8908 _reflns_number_gt 5622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0438P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8908 _refine_ls_number_parameters 701 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 1.0000 0.5000 0.5000 0.02499(19) Uani 1 2 d S . . Mn2 Mn 0.89761(5) 0.49349(4) 0.31488(3) 0.02361(14) Uani 1 1 d . . . Mn3 Mn 1.13283(5) 1.00558(4) 0.18259(3) 0.02459(15) Uani 1 1 d . . . Mn4 Mn 1.0000 1.0000 0.0000 0.02280(19) Uani 1 2 d S . . O1 O 0.7926(3) 0.4519(2) 0.41087(14) 0.0402(7) Uani 1 1 d . . . O2 O 0.6669(3) 0.5029(2) 0.32131(14) 0.0397(7) Uani 1 1 d . . . O3 O 0.1294(3) 0.47410(19) 0.30376(13) 0.0372(7) Uani 1 1 d . . . O4 O 0.0690(3) 0.45598(19) 0.40366(13) 0.0357(6) Uani 1 1 d . . . O5 O 0.4207(3) 0.2982(2) 0.53754(14) 0.0418(7) Uani 1 1 d . . . O6 O 1.0428(3) 0.64759(19) 0.48278(14) 0.0471(8) Uani 1 1 d . . . O7 O 1.0017(3) 0.64655(18) 0.36430(13) 0.0351(6) Uani 1 1 d . . . O8 O 1.1990(3) 0.95670(18) 0.28295(12) 0.0311(6) Uani 1 1 d . . . O9 O 1.2628(3) 1.09884(19) 0.36459(13) 0.0448(7) Uani 1 1 d . . . O10 O 1.4009(3) 0.9904(2) 0.60111(13) 0.0434(7) Uani 1 1 d . . . O11 O 1.0223(3) 0.85212(18) 0.13917(13) 0.0378(7) Uani 1 1 d . . . O12 O 0.9666(3) 0.85540(18) 0.02135(13) 0.0396(7) Uani 1 1 d . . . O13 O 0.8668(3) 0.53404(18) 0.21291(12) 0.0337(6) Uani 1 1 d . . . O14 O 0.8023(4) 0.3924(2) 0.13167(14) 0.0552(9) Uani 1 1 d . . . O15 O 0.5889(3) 0.5180(2) -0.09475(14) 0.0504(8) Uani 1 1 d . . . O16 O 0.8851(3) 1.0247(2) 0.19921(13) 0.0400(7) Uani 1 1 d . . . O17 O 0.9678(2) 1.05115(17) 0.10602(12) 0.0278(6) Uani 1 1 d . . . O18 O 0.3429(3) 1.0087(2) 0.16221(15) 0.0460(7) Uani 1 1 d . . . O19 O 0.2298(3) 1.0501(2) 0.06246(15) 0.0482(8) Uani 1 1 d . . . O20 O 0.6287(3) 1.2333(2) -0.02763(13) 0.0391(7) Uani 1 1 d . . . O21 O 0.9109(3) 0.85547(19) 0.55154(14) 0.0474(7) Uani 1 1 d . . . H1W H 0.8409 0.8592 0.5690 0.071 Uiso 1 1 d R . . H2W H 0.9656 0.8356 0.5841 0.071 Uiso 1 1 d R . . O22 O 0.0965(4) 0.3122(3) 0.19117(17) 0.0816(11) Uani 1 1 d . . . H3W H 0.0745 0.3579 0.2152 0.122 Uiso 1 1 d R . . H4W H 0.1736 0.3356 0.1791 0.122 Uiso 1 1 d R . . O23 O 0.5218(3) 0.2438(3) 0.24880(19) 0.1031(14) Uani 1 1 d . . . H5W H 0.5283 0.1849 0.2385 0.155 Uiso 1 1 d R . . H6W H 0.4409 0.2477 0.2553 0.155 Uiso 1 1 d R . . O24 O 0.9380(4) 0.1945(3) 0.32370(18) 0.0807(11) Uani 1 1 d . . . H7W H 0.9171 0.2384 0.3004 0.121 Uiso 1 1 d R . . H8W H 0.9229 0.1466 0.2888 0.121 Uiso 1 1 d R . . O25 O 0.8025(3) 0.33481(17) 0.25705(13) 0.0369(6) Uani 1 1 d . . . H9W H 0.7935 0.3312 0.2122 0.055 Uiso 1 1 d R . . H10W H 0.7151 0.3145 0.2591 0.055 Uiso 1 1 d R . . O26 O 1.2197(3) 1.16450(18) 0.23860(13) 0.0425(7) Uani 1 1 d . . . H11W H 1.2389 1.1684 0.2841 0.064 Uiso 1 1 d R . . H12W H 1.1750 1.2075 0.2283 0.064 Uiso 1 1 d R . . N1 N 0.2839(4) 0.7908(3) 0.24392(18) 0.0427(9) Uani 1 1 d . . . N2 N 0.4397(3) 0.7306(3) 0.20380(17) 0.0396(8) Uani 1 1 d . . . N3 N 0.7472(3) 0.7766(3) 0.29348(17) 0.0373(8) Uani 1 1 d . . . N4 N 0.8195(3) 0.8364(3) 0.40902(18) 0.0411(8) Uani 1 1 d . . . C1 C 0.6739(4) 0.4642(3) 0.3762(2) 0.0295(9) Uani 1 1 d . . . C2 C 0.5402(3) 0.4293(3) 0.40045(18) 0.0254(8) Uani 1 1 d . . . C3 C 0.5467(4) 0.3774(3) 0.45671(19) 0.0302(9) Uani 1 1 d . . . H3 H 0.6321 0.3617 0.4772 0.036 Uiso 1 1 calc R . . C4 C 0.4265(4) 0.3490(3) 0.48226(19) 0.0298(9) Uani 1 1 d . . . C5 C 0.2995(4) 0.3747(3) 0.45217(18) 0.0293(9) Uani 1 1 d . . . H5 H 0.2198 0.3580 0.4705 0.035 Uiso 1 1 calc R . . C6 C 0.2918(4) 0.4246(3) 0.39545(18) 0.0254(8) Uani 1 1 d . . . C7 C 0.4117(3) 0.4505(3) 0.36863(18) 0.0259(8) Uani 1 1 d . . . H7 H 0.4057 0.4820 0.3293 0.031 Uiso 1 1 calc R . . C8 C 0.1565(4) 0.4534(3) 0.36544(19) 0.0262(8) Uani 1 1 d . . . C9 C 0.5458(4) 0.2687(3) 0.5690(2) 0.0447(11) Uani 1 1 d . . . H9A H 0.5665 0.2269 0.5323 0.067 Uiso 1 1 calc R . . H9B H 0.5272 0.2324 0.6058 0.067 Uiso 1 1 calc R . . H9C H 0.6282 0.3269 0.5901 0.067 Uiso 1 1 calc R . . C10 C 1.0572(4) 0.6880(3) 0.4299(2) 0.0277(8) Uani 1 1 d . . . C11 C 1.1482(4) 0.7946(3) 0.44711(18) 0.0249(8) Uani 1 1 d . . . C12 C 1.2280(4) 0.8414(3) 0.51868(18) 0.0288(9) Uani 1 1 d . . . H12 H 1.2236 0.8067 0.5560 0.035 Uiso 1 1 calc R . . C13 C 1.3139(4) 0.9400(3) 0.53343(19) 0.0312(9) Uani 1 1 d . . . C14 C 1.3152(4) 0.9930(3) 0.47822(19) 0.0319(9) Uani 1 1 d . . . H14 H 1.3694 1.0599 0.4888 0.038 Uiso 1 1 calc R . . C15 C 1.2363(4) 0.9470(3) 0.40717(19) 0.0275(8) Uani 1 1 d . . . C16 C 1.1546(4) 0.8470(3) 0.39162(18) 0.0247(8) Uani 1 1 d . . . H16 H 1.1041 0.8152 0.3440 0.030 Uiso 1 1 calc R . . C17 C 1.2340(4) 1.0060(3) 0.3479(2) 0.0294(9) Uani 1 1 d . . . C18 C 1.4113(5) 0.9335(3) 0.6571(2) 0.0555(13) Uani 1 1 d . . . H18A H 1.3185 0.9138 0.6669 0.083 Uiso 1 1 calc R . . H18B H 1.4843 0.9735 0.7003 0.083 Uiso 1 1 calc R . . H18C H 1.4382 0.8751 0.6418 0.083 Uiso 1 1 calc R . . C19 C 0.8266(4) 0.4843(3) 0.14922(19) 0.0307(9) Uani 1 1 d . . . C20 C 0.8080(4) 0.5451(3) 0.09086(18) 0.0292(9) Uani 1 1 d . . . C21 C 0.8880(4) 0.6461(3) 0.10699(19) 0.0281(8) Uani 1 1 d . . . H21 H 0.9529 0.6740 0.1528 0.034 Uiso 1 1 calc R . . C22 C 0.8721(4) 0.7050(3) 0.05583(18) 0.0264(8) Uani 1 1 d . . . C23 C 0.7737(4) 0.6639(3) -0.01324(19) 0.0337(9) Uani 1 1 d . . . H23 H 0.7640 0.7028 -0.0482 0.040 Uiso 1 1 calc R . . C24 C 0.6903(4) 0.5638(3) -0.02901(19) 0.0357(10) Uani 1 1 d . . . C25 C 0.7083(4) 0.5047(3) 0.02256(19) 0.0361(10) Uani 1 1 d . . . H25A H 0.6535 0.4379 0.0114 0.043 Uiso 1 1 calc R . . C26 C 0.9590(4) 0.8120(3) 0.0731(2) 0.0271(8) Uani 1 1 d . . . C27 C 0.5512(5) 0.5822(3) -0.1432(2) 0.0614(14) Uani 1 1 d . . . H27A H 0.5200 0.6331 -0.1191 0.092 Uiso 1 1 calc R . . H27B H 0.4733 0.5436 -0.1850 0.092 Uiso 1 1 calc R . . H27C H 0.6352 0.6129 -0.1578 0.092 Uiso 1 1 calc R . . C28 C 0.8700(4) 1.0497(3) 0.13914(19) 0.0258(8) Uani 1 1 d . . . C29 C 0.7393(3) 1.0820(3) 0.10532(18) 0.0244(8) Uani 1 1 d . . . C30 C 0.7495(4) 1.1418(2) 0.05409(18) 0.0247(8) Uani 1 1 d . . . H30 H 0.8362 1.1618 0.0418 0.030 Uiso 1 1 calc R . . C31 C 0.6288(4) 1.1714(3) 0.02152(18) 0.0276(8) Uani 1 1 d . . . C32 C 0.4964(4) 1.1372(3) 0.03725(19) 0.0308(9) Uani 1 1 d . . . H32 H 0.4147 1.1548 0.0137 0.037 Uiso 1 1 calc R . . C33 C 0.4863(4) 1.0773(3) 0.08779(19) 0.0278(8) Uani 1 1 d . . . C34 C 0.6100(3) 1.0518(3) 0.12318(18) 0.0275(8) Uani 1 1 d . . . H34 H 0.6052 1.0144 0.1589 0.033 Uiso 1 1 calc R . . C35 C 0.7683(4) 1.2779(3) -0.0379(2) 0.0422(10) Uani 1 1 d . . . H35A H 0.8384 1.3094 0.0082 0.063 Uiso 1 1 calc R . . H35B H 0.7593 1.3269 -0.0674 0.063 Uiso 1 1 calc R . . H35C H 0.8005 1.2272 -0.0615 0.063 Uiso 1 1 calc R . . C36 C 0.3433(4) 1.0421(3) 0.1051(2) 0.0336(9) Uani 1 1 d . . . C37 C 0.2517(5) 0.6910(3) 0.2475(2) 0.0451(11) Uani 1 1 d . . . H37 H 0.1770 0.6560 0.2640 0.054 Uiso 1 1 calc R . . C38 C 0.3480(5) 0.6535(3) 0.2229(2) 0.0487(11) Uani 1 1 d . . . H38 H 0.3521 0.5880 0.2193 0.058 Uiso 1 1 calc R . . C39 C 0.3971(4) 0.8118(3) 0.2177(2) 0.0410(10) Uani 1 1 d . . . H39 H 0.4409 0.8744 0.2100 0.049 Uiso 1 1 calc R . . C40 C 0.5613(5) 0.7255(4) 0.1731(2) 0.0532(12) Uani 1 1 d . . . H40A H 0.5988 0.7887 0.1600 0.064 Uiso 1 1 calc R . . H40B H 0.5246 0.6741 0.1294 0.064 Uiso 1 1 calc R . . C41 C 0.6861(5) 0.7026(3) 0.2258(2) 0.0547(13) Uani 1 1 d . . . H41A H 0.6503 0.6372 0.2364 0.066 Uiso 1 1 calc R . . H41B H 0.7630 0.7004 0.2031 0.066 Uiso 1 1 calc R . . C42 C 0.8115(4) 0.8776(3) 0.3027(3) 0.0483(12) Uani 1 1 d . . . H42 H 0.8219 0.9136 0.2666 0.058 Uiso 1 1 calc R . . C43 C 0.8564(4) 0.9137(3) 0.3744(3) 0.0487(11) Uani 1 1 d . . . H43 H 0.9045 0.9800 0.3969 0.058 Uiso 1 1 calc R . . C44 C 0.7551(4) 0.7550(3) 0.3584(2) 0.0384(10) Uani 1 1 d . . . H44 H 0.7201 0.6914 0.3669 0.046 Uiso 1 1 calc 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 Mn1 0.0243(4) 0.0297(5) 0.0249(4) 0.0145(4) 0.0087(3) 0.0085(4) Mn2 0.0217(3) 0.0266(3) 0.0246(3) 0.0104(2) 0.0071(2) 0.0075(2) Mn3 0.0212(3) 0.0271(3) 0.0263(3) 0.0107(3) 0.0059(2) 0.0068(2) Mn4 0.0212(4) 0.0264(4) 0.0235(4) 0.0124(3) 0.0074(3) 0.0070(3) O1 0.0198(13) 0.0586(19) 0.0439(17) 0.0167(14) 0.0084(12) 0.0119(13) O2 0.0303(15) 0.0575(19) 0.0375(16) 0.0214(14) 0.0160(13) 0.0115(13) O3 0.0308(15) 0.0546(18) 0.0331(15) 0.0175(14) 0.0100(12) 0.0195(13) O4 0.0279(14) 0.0512(18) 0.0421(16) 0.0168(13) 0.0217(13) 0.0212(13) O5 0.0328(15) 0.065(2) 0.0444(16) 0.0361(15) 0.0176(13) 0.0259(14) O6 0.074(2) 0.0296(16) 0.0348(16) 0.0139(13) 0.0172(15) 0.0045(15) O7 0.0410(16) 0.0280(15) 0.0292(15) 0.0071(12) 0.0036(12) 0.0030(12) O8 0.0384(15) 0.0315(15) 0.0248(14) 0.0079(12) 0.0094(12) 0.0111(12) O9 0.076(2) 0.0259(16) 0.0363(16) 0.0101(13) 0.0247(15) 0.0105(15) O10 0.0487(17) 0.0441(18) 0.0240(15) 0.0001(13) 0.0044(13) -0.0010(14) O11 0.0432(16) 0.0250(15) 0.0351(16) 0.0056(12) 0.0020(13) 0.0017(12) O12 0.0563(18) 0.0273(15) 0.0402(16) 0.0187(13) 0.0192(14) 0.0098(13) O13 0.0482(16) 0.0280(15) 0.0232(14) 0.0084(12) 0.0080(12) 0.0088(13) O14 0.102(3) 0.0263(17) 0.0330(16) 0.0086(13) 0.0177(16) 0.0111(17) O15 0.0572(19) 0.0422(18) 0.0311(16) 0.0053(14) -0.0107(14) 0.0017(15) O16 0.0383(16) 0.0575(19) 0.0367(16) 0.0289(14) 0.0147(13) 0.0224(14) O17 0.0229(13) 0.0383(15) 0.0290(14) 0.0134(12) 0.0113(11) 0.0137(12) O18 0.0320(16) 0.064(2) 0.0472(18) 0.0176(16) 0.0227(14) 0.0096(14) O19 0.0197(14) 0.057(2) 0.064(2) 0.0086(16) 0.0062(14) 0.0109(13) O20 0.0328(15) 0.0539(18) 0.0412(16) 0.0271(14) 0.0129(13) 0.0205(14) O21 0.0457(17) 0.055(2) 0.0447(17) 0.0153(15) 0.0140(14) 0.0172(15) O22 0.105(3) 0.081(3) 0.072(2) 0.009(2) 0.033(2) 0.046(2) O23 0.050(2) 0.112(3) 0.125(4) 0.009(3) 0.027(2) -0.008(2) O24 0.097(3) 0.078(3) 0.073(2) 0.032(2) 0.008(2) 0.045(2) O25 0.0373(15) 0.0322(16) 0.0394(16) 0.0105(13) 0.0097(13) 0.0063(12) O26 0.0502(17) 0.0348(16) 0.0384(16) 0.0058(13) 0.0105(14) 0.0081(14) N1 0.041(2) 0.047(2) 0.045(2) 0.0175(18) 0.0137(17) 0.0156(18) N2 0.039(2) 0.046(2) 0.0347(19) 0.0056(17) 0.0057(16) 0.0221(18) N3 0.0348(19) 0.048(2) 0.035(2) 0.0107(17) 0.0114(16) 0.0194(17) N4 0.038(2) 0.051(2) 0.042(2) 0.0136(19) 0.0164(17) 0.0201(18) C1 0.024(2) 0.034(2) 0.030(2) 0.0025(18) 0.0098(17) 0.0080(17) C2 0.0192(18) 0.029(2) 0.029(2) 0.0080(17) 0.0078(16) 0.0056(16) C3 0.0214(19) 0.039(2) 0.035(2) 0.0142(18) 0.0084(17) 0.0126(17) C4 0.027(2) 0.039(2) 0.028(2) 0.0137(18) 0.0101(17) 0.0122(18) C5 0.0202(18) 0.038(2) 0.032(2) 0.0081(18) 0.0116(16) 0.0076(17) C6 0.0210(18) 0.030(2) 0.026(2) 0.0057(17) 0.0073(16) 0.0074(16) C7 0.0247(19) 0.034(2) 0.0220(19) 0.0107(17) 0.0080(16) 0.0112(17) C8 0.0183(18) 0.027(2) 0.032(2) 0.0048(17) 0.0075(17) 0.0053(16) C9 0.038(2) 0.058(3) 0.045(3) 0.029(2) 0.010(2) 0.021(2) C10 0.0261(19) 0.031(2) 0.030(2) 0.0141(19) 0.0083(17) 0.0112(17) C11 0.0234(19) 0.026(2) 0.028(2) 0.0076(17) 0.0093(16) 0.0087(16) C12 0.028(2) 0.037(2) 0.025(2) 0.0126(18) 0.0064(17) 0.0145(18) C13 0.030(2) 0.038(2) 0.021(2) -0.0002(18) 0.0056(17) 0.0052(18) C14 0.034(2) 0.028(2) 0.032(2) 0.0061(18) 0.0119(18) 0.0055(18) C15 0.0263(19) 0.027(2) 0.030(2) 0.0088(17) 0.0095(17) 0.0079(17) C16 0.0244(18) 0.030(2) 0.0229(19) 0.0065(16) 0.0070(15) 0.0118(16) C17 0.030(2) 0.028(2) 0.034(2) 0.0109(18) 0.0152(18) 0.0075(17) C18 0.051(3) 0.075(4) 0.026(2) 0.010(2) -0.003(2) 0.007(3) C19 0.038(2) 0.027(2) 0.027(2) 0.0079(18) 0.0130(18) 0.0037(18) C20 0.035(2) 0.028(2) 0.023(2) 0.0077(17) 0.0083(17) 0.0062(18) C21 0.031(2) 0.028(2) 0.0221(19) 0.0034(17) 0.0052(16) 0.0064(17) C22 0.030(2) 0.023(2) 0.026(2) 0.0063(17) 0.0103(17) 0.0052(16) C23 0.041(2) 0.034(2) 0.026(2) 0.0139(18) 0.0051(18) 0.0113(19) C24 0.043(2) 0.032(2) 0.023(2) 0.0028(18) -0.0013(18) 0.0047(19) C25 0.047(2) 0.028(2) 0.026(2) 0.0049(18) 0.0052(18) 0.0031(19) C26 0.028(2) 0.024(2) 0.031(2) 0.0077(18) 0.0075(17) 0.0097(17) C27 0.065(3) 0.067(3) 0.035(3) 0.012(2) -0.013(2) 0.015(3) C28 0.0241(19) 0.028(2) 0.028(2) 0.0116(17) 0.0085(17) 0.0078(16) C29 0.0199(18) 0.028(2) 0.027(2) 0.0084(16) 0.0093(16) 0.0065(16) C30 0.0209(18) 0.029(2) 0.029(2) 0.0100(17) 0.0127(16) 0.0091(16) C31 0.030(2) 0.034(2) 0.024(2) 0.0087(17) 0.0087(16) 0.0154(17) C32 0.0226(19) 0.037(2) 0.033(2) 0.0054(18) 0.0040(17) 0.0138(17) C33 0.0242(19) 0.031(2) 0.028(2) 0.0027(17) 0.0081(16) 0.0090(17) C34 0.0229(19) 0.034(2) 0.030(2) 0.0128(17) 0.0097(16) 0.0094(17) C35 0.041(2) 0.052(3) 0.044(2) 0.027(2) 0.019(2) 0.017(2) C36 0.027(2) 0.032(2) 0.039(2) -0.0018(19) 0.0084(19) 0.0082(18) C37 0.043(3) 0.045(3) 0.048(3) 0.021(2) 0.009(2) 0.012(2) C38 0.062(3) 0.036(3) 0.049(3) 0.013(2) 0.012(2) 0.019(2) C39 0.047(3) 0.035(2) 0.042(2) 0.008(2) 0.012(2) 0.015(2) C40 0.055(3) 0.074(3) 0.037(2) 0.008(2) 0.012(2) 0.032(3) C41 0.061(3) 0.067(3) 0.051(3) 0.010(3) 0.019(2) 0.042(3) C42 0.041(3) 0.049(3) 0.065(3) 0.033(3) 0.021(2) 0.015(2) C43 0.033(2) 0.041(3) 0.068(3) 0.010(2) 0.009(2) 0.008(2) C44 0.037(2) 0.045(3) 0.046(3) 0.024(2) 0.020(2) 0.020(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 O6 2.107(3) . ? Mn1 O6 2.107(3) 2_766 ? Mn1 O4 2.213(3) 2_666 ? Mn1 O4 2.213(3) 1_655 ? Mn1 O1 2.217(3) 2_766 ? Mn1 O1 2.217(3) . ? Mn2 O13 2.108(3) . ? Mn2 O7 2.127(3) . ? Mn2 O25 2.225(3) . ? Mn2 O4 2.316(3) 1_655 ? Mn2 O2 2.341(3) . ? Mn2 O1 2.415(3) . ? Mn2 O3 2.422(3) 1_655 ? Mn3 O11 2.121(3) . ? Mn3 O8 2.160(3) . ? Mn3 O18 2.190(3) 1_655 ? Mn3 O17 2.203(2) . ? Mn3 O26 2.216(3) . ? Mn4 O12 2.097(3) 2_775 ? Mn4 O12 2.097(3) . ? Mn4 O19 2.177(3) 1_655 ? Mn4 O19 2.177(3) 2_675 ? Mn4 O17 2.220(3) . ? Mn4 O17 2.220(3) 2_775 ? O1 C1 1.263(4) . ? O2 C1 1.257(4) . ? O3 C8 1.253(4) . ? O3 Mn2 2.422(3) 1_455 ? O4 C8 1.273(4) . ? O4 Mn1 2.213(3) 1_455 ? O4 Mn2 2.316(3) 1_455 ? O5 C4 1.372(4) . ? O5 C9 1.420(4) . ? O6 C10 1.260(4) . ? O7 C10 1.257(4) . ? O8 C17 1.281(4) . ? O9 C17 1.250(4) . ? O10 C13 1.371(4) . ? O10 C18 1.434(5) . ? O11 C26 1.269(4) . ? O12 C26 1.252(4) . ? O13 C19 1.258(4) . ? O14 C19 1.243(4) . ? O15 C24 1.376(4) . ? O15 C27 1.436(5) . ? O16 C28 1.250(4) . ? O17 C28 1.281(4) . ? O18 C36 1.262(4) . ? O18 Mn3 2.190(3) 1_455 ? O19 C36 1.257(4) . ? O19 Mn4 2.177(3) 1_455 ? O20 C31 1.376(4) . ? O20 C35 1.437(4) . ? O21 H1W 0.8500 . ? O21 H2W 0.8500 . ? O22 H3W 0.8501 . ? O22 H4W 0.8500 . ? O23 H5W 0.8500 . ? O23 H6W 0.8500 . ? O24 H7W 0.8500 . ? O24 H8W 0.8499 . ? O25 H9W 0.8500 . ? O25 H10W 0.8500 . ? O26 H11W 0.8501 . ? O26 H12W 0.8500 . ? N1 C39 1.321(5) . ? N1 C37 1.379(5) . ? N2 C39 1.333(5) . ? N2 C38 1.385(5) . ? N2 C40 1.476(5) . ? N3 C44 1.326(4) . ? N3 C42 1.377(5) . ? N3 C41 1.461(5) . ? N4 C44 1.316(5) . ? N4 C43 1.374(5) . ? C1 C2 1.497(5) . ? C2 C7 1.387(4) . ? C2 C3 1.392(5) . ? C3 C4 1.383(5) . ? C3 H3 0.9300 . ? C4 C5 1.400(5) . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 C7 1.392(5) . ? C6 C8 1.493(5) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.495(5) . ? C11 C16 1.391(5) . ? C11 C12 1.401(5) . ? C12 C13 1.389(5) . ? C12 H12 0.9300 . ? C13 C14 1.387(5) . ? C14 C15 1.389(5) . ? C14 H14 0.9300 . ? C15 C16 1.392(5) . ? C15 C17 1.506(5) . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.512(5) . ? C20 C25 1.394(5) . ? C20 C21 1.400(5) . ? C21 C22 1.381(5) . ? C21 H21 0.9300 . ? C22 C23 1.402(5) . ? C22 C26 1.488(5) . ? C23 C24 1.398(5) . ? C23 H23 0.9300 . ? C24 C25 1.391(5) . ? C25 H25A 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.499(5) . ? C29 C34 1.383(5) . ? C29 C30 1.393(4) . ? C30 C31 1.390(4) . ? C30 H30 0.9300 . ? C31 C32 1.396(5) . ? C32 C33 1.384(5) . ? C32 H32 0.9300 . ? C33 C34 1.399(5) . ? C33 C36 1.508(5) . ? C34 H34 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C37 C38 1.347(5) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 C41 1.527(5) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.344(6) . ? C42 H42 0.9300 . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Mn1 O6 180.000(1) . 2_766 ? O6 Mn1 O4 90.77(10) . 2_666 ? O6 Mn1 O4 89.23(10) 2_766 2_666 ? O6 Mn1 O4 89.23(10) . 1_655 ? O6 Mn1 O4 90.77(10) 2_766 1_655 ? O4 Mn1 O4 180.00(6) 2_666 1_655 ? O6 Mn1 O1 88.50(10) . 2_766 ? O6 Mn1 O1 91.50(10) 2_766 2_766 ? O4 Mn1 O1 76.61(10) 2_666 2_766 ? O4 Mn1 O1 103.39(10) 1_655 2_766 ? O6 Mn1 O1 91.50(10) . . ? O6 Mn1 O1 88.50(10) 2_766 . ? O4 Mn1 O1 103.39(10) 2_666 . ? O4 Mn1 O1 76.61(10) 1_655 . ? O1 Mn1 O1 180.0 2_766 . ? O13 Mn2 O7 88.93(10) . . ? O13 Mn2 O25 87.88(10) . . ? O7 Mn2 O25 174.81(10) . . ? O13 Mn2 O4 141.84(9) . 1_655 ? O7 Mn2 O4 87.27(10) . 1_655 ? O25 Mn2 O4 92.72(10) . 1_655 ? O13 Mn2 O2 92.56(9) . . ? O7 Mn2 O2 93.33(10) . . ? O25 Mn2 O2 90.90(10) . . ? O4 Mn2 O2 125.56(9) 1_655 . ? O13 Mn2 O1 147.22(10) . . ? O7 Mn2 O1 95.62(10) . . ? O25 Mn2 O1 89.27(10) . . ? O4 Mn2 O1 70.91(9) 1_655 . ? O2 Mn2 O1 54.84(9) . . ? O13 Mn2 O3 86.91(9) . 1_655 ? O7 Mn2 O3 89.97(10) . 1_655 ? O25 Mn2 O3 85.77(9) . 1_655 ? O4 Mn2 O3 55.15(9) 1_655 1_655 ? O2 Mn2 O3 176.65(9) . 1_655 ? O1 Mn2 O3 125.42(8) . 1_655 ? O11 Mn3 O8 84.71(10) . . ? O11 Mn3 O18 98.37(11) . 1_655 ? O8 Mn3 O18 91.02(10) . 1_655 ? O11 Mn3 O17 91.72(10) . . ? O8 Mn3 O17 148.92(9) . . ? O18 Mn3 O17 120.02(10) 1_655 . ? O11 Mn3 O26 169.97(10) . . ? O8 Mn3 O26 91.50(10) . . ? O18 Mn3 O26 90.97(10) 1_655 . ? O17 Mn3 O26 86.73(10) . . ? O12 Mn4 O12 180.0 2_775 . ? O12 Mn4 O19 85.84(11) 2_775 1_655 ? O12 Mn4 O19 94.16(11) . 1_655 ? O12 Mn4 O19 94.16(11) 2_775 2_675 ? O12 Mn4 O19 85.84(11) . 2_675 ? O19 Mn4 O19 180.0 1_655 2_675 ? O12 Mn4 O17 91.13(10) 2_775 . ? O12 Mn4 O17 88.87(10) . . ? O19 Mn4 O17 82.84(10) 1_655 . ? O19 Mn4 O17 97.16(10) 2_675 . ? O12 Mn4 O17 88.87(10) 2_775 2_775 ? O12 Mn4 O17 91.13(10) . 2_775 ? O19 Mn4 O17 97.16(10) 1_655 2_775 ? O19 Mn4 O17 82.84(10) 2_675 2_775 ? O17 Mn4 O17 180.00(5) . 2_775 ? C1 O1 Mn1 152.1(3) . . ? C1 O1 Mn2 89.9(2) . . ? Mn1 O1 Mn2 97.25(10) . . ? C1 O2 Mn2 93.4(2) . . ? C8 O3 Mn2 89.8(2) . 1_455 ? C8 O4 Mn1 157.0(2) . 1_455 ? C8 O4 Mn2 94.2(2) . 1_455 ? Mn1 O4 Mn2 100.33(10) 1_455 1_455 ? C4 O5 C9 117.4(3) . . ? C10 O6 Mn1 135.0(2) . . ? C10 O7 Mn2 130.4(2) . . ? C17 O8 Mn3 128.8(2) . . ? C13 O10 C18 116.6(3) . . ? C26 O11 Mn3 126.8(2) . . ? C26 O12 Mn4 139.3(2) . . ? C19 O13 Mn2 133.0(2) . . ? C24 O15 C27 116.5(3) . . ? C28 O17 Mn3 101.9(2) . . ? C28 O17 Mn4 143.1(2) . . ? Mn3 O17 Mn4 102.79(10) . . ? C36 O18 Mn3 107.3(2) . 1_455 ? C36 O19 Mn4 154.7(3) . 1_455 ? C31 O20 C35 116.0(3) . . ? H1W O21 H2W 102.4 . . ? H3W O22 H4W 111.4 . . ? H5W O23 H6W 115.7 . . ? H7W O24 H8W 100.2 . . ? Mn2 O25 H9W 109.6 . . ? Mn2 O25 H10W 108.5 . . ? H9W O25 H10W 104.1 . . ? Mn3 O26 H11W 109.6 . . ? Mn3 O26 H12W 122.6 . . ? H11W O26 H12W 107.2 . . ? C39 N1 C37 107.6(3) . . ? C39 N2 C38 107.1(4) . . ? C39 N2 C40 125.5(4) . . ? C38 N2 C40 127.4(4) . . ? C44 N3 C42 107.9(3) . . ? C44 N3 C41 124.2(4) . . ? C42 N3 C41 127.8(4) . . ? C44 N4 C43 106.8(4) . . ? O2 C1 O1 120.8(3) . . ? O2 C1 C2 120.3(3) . . ? O1 C1 C2 118.9(3) . . ? C7 C2 C3 119.9(3) . . ? C7 C2 C1 120.7(3) . . ? C3 C2 C1 119.3(3) . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? O5 C4 C3 125.2(3) . . ? O5 C4 C5 115.2(3) . . ? C3 C4 C5 119.6(3) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.7(3) . . ? C5 C6 C8 119.4(3) . . ? C7 C6 C8 120.8(3) . . ? C2 C7 C6 120.1(3) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? O3 C8 O4 120.8(3) . . ? O3 C8 C6 120.6(3) . . ? O4 C8 C6 118.6(3) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O7 C10 O6 125.7(3) . . ? O7 C10 C11 117.4(3) . . ? O6 C10 C11 116.8(3) . . ? C16 C11 C12 120.1(3) . . ? C16 C11 C10 119.7(3) . . ? C12 C11 C10 120.3(3) . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? O10 C13 C14 116.2(3) . . ? O10 C13 C12 123.5(3) . . ? C14 C13 C12 120.2(3) . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 119.5(3) . . ? C14 C15 C17 120.2(3) . . ? C16 C15 C17 120.2(3) . . ? C11 C16 C15 120.2(3) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O9 C17 O8 124.2(3) . . ? O9 C17 C15 118.5(3) . . ? O8 C17 C15 117.2(3) . . ? O10 C18 H18A 109.5 . . ? O10 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O10 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O14 C19 O13 125.8(3) . . ? O14 C19 C20 119.3(3) . . ? O13 C19 C20 114.9(3) . . ? C25 C20 C21 119.0(3) . . ? C25 C20 C19 121.9(3) . . ? C21 C20 C19 119.0(3) . . ? C22 C21 C20 121.0(3) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 C26 120.7(3) . . ? C23 C22 C26 119.4(3) . . ? C24 C23 C22 119.3(3) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? O15 C24 C25 116.5(3) . . ? O15 C24 C23 123.2(3) . . ? C25 C24 C23 120.3(3) . . ? C24 C25 C20 120.4(3) . . ? C24 C25 H25A 119.8 . . ? C20 C25 H25A 119.8 . . ? O12 C26 O11 124.8(3) . . ? O12 C26 C22 117.8(3) . . ? O11 C26 C22 117.5(3) . . ? O15 C27 H27A 109.5 . . ? O15 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O15 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O16 C28 O17 120.8(3) . . ? O16 C28 C29 120.7(3) . . ? O17 C28 C29 118.5(3) . . ? C34 C29 C30 120.2(3) . . ? C34 C29 C28 121.1(3) . . ? C30 C29 C28 118.7(3) . . ? C31 C30 C29 119.4(3) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? O20 C31 C30 124.1(3) . . ? O20 C31 C32 115.6(3) . . ? C30 C31 C32 120.2(3) . . ? C33 C32 C31 120.2(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 119.4(3) . . ? C32 C33 C36 119.6(3) . . ? C34 C33 C36 120.9(3) . . ? C29 C34 C33 120.4(3) . . ? C29 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? O20 C35 H35A 109.5 . . ? O20 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O20 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O19 C36 O18 123.0(4) . . ? O19 C36 C33 117.9(4) . . ? O18 C36 C33 119.1(3) . . ? C38 C37 N1 107.6(4) . . ? C38 C37 H37 126.2 . . ? N1 C37 H37 126.2 . . ? C37 C38 N2 107.4(4) . . ? C37 C38 H38 126.3 . . ? N2 C38 H38 126.3 . . ? N1 C39 N2 110.3(4) . . ? N1 C39 H39 124.9 . . ? N2 C39 H39 124.9 . . ? N2 C40 C41 112.5(3) . . ? N2 C40 H40A 109.1 . . ? C41 C40 H40A 109.1 . . ? N2 C40 H40B 109.1 . . ? C41 C40 H40B 109.1 . . ? H40A C40 H40B 107.8 . . ? N3 C41 C40 112.5(3) . . ? N3 C41 H41A 109.1 . . ? C40 C41 H41A 109.1 . . ? N3 C41 H41B 109.1 . . ? C40 C41 H41B 109.1 . . ? H41A C41 H41B 107.8 . . ? C43 C42 N3 106.2(4) . . ? C43 C42 H42 126.9 . . ? N3 C42 H42 126.9 . . ? C42 C43 N4 108.7(4) . . ? C42 C43 H43 125.6 . . ? N4 C43 H43 125.6 . . ? N4 C44 N3 110.4(4) . . ? N4 C44 H44 124.8 . . ? N3 C44 H44 124.8 . . ? 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 O6 Mn1 O1 C1 -43.5(5) . . . . ? O6 Mn1 O1 C1 136.5(5) 2_766 . . . ? O4 Mn1 O1 C1 47.7(5) 2_666 . . . ? O4 Mn1 O1 C1 -132.3(5) 1_655 . . . ? O1 Mn1 O1 C1 -163(100) 2_766 . . . ? O6 Mn1 O1 Mn2 60.14(11) . . . . ? O6 Mn1 O1 Mn2 -119.86(11) 2_766 . . . ? O4 Mn1 O1 Mn2 151.29(9) 2_666 . . . ? O4 Mn1 O1 Mn2 -28.71(9) 1_655 . . . ? O1 Mn1 O1 Mn2 -59(100) 2_766 . . . ? O13 Mn2 O1 C1 -0.8(3) . . . . ? O7 Mn2 O1 C1 96.0(2) . . . . ? O25 Mn2 O1 C1 -85.7(2) . . . . ? O4 Mn2 O1 C1 -178.8(2) 1_655 . . . ? O2 Mn2 O1 C1 5.9(2) . . . . ? O3 Mn2 O1 C1 -170.0(2) 1_655 . . . ? O13 Mn2 O1 Mn1 -153.72(14) . . . . ? O7 Mn2 O1 Mn1 -56.94(11) . . . . ? O25 Mn2 O1 Mn1 121.33(10) . . . . ? O4 Mn2 O1 Mn1 28.20(9) 1_655 . . . ? O2 Mn2 O1 Mn1 -147.05(15) . . . . ? O3 Mn2 O1 Mn1 37.04(14) 1_655 . . . ? O13 Mn2 O2 C1 170.4(2) . . . . ? O7 Mn2 O2 C1 -100.5(2) . . . . ? O25 Mn2 O2 C1 82.5(2) . . . . ? O4 Mn2 O2 C1 -11.5(3) 1_655 . . . ? O1 Mn2 O2 C1 -6.0(2) . . . . ? O3 Mn2 O2 C1 89.7(15) 1_655 . . . ? O6 Mn1 O6 C10 133(100) 2_766 . . . ? O4 Mn1 O6 C10 -161.1(4) 2_666 . . . ? O4 Mn1 O6 C10 18.9(4) 1_655 . . . ? O1 Mn1 O6 C10 122.3(4) 2_766 . . . ? O1 Mn1 O6 C10 -57.7(4) . . . . ? O13 Mn2 O7 C10 -179.5(3) . . . . ? O25 Mn2 O7 C10 -127.5(10) . . . . ? O4 Mn2 O7 C10 -37.5(3) 1_655 . . . ? O2 Mn2 O7 C10 88.0(3) . . . . ? O1 Mn2 O7 C10 33.0(3) . . . . ? O3 Mn2 O7 C10 -92.6(3) 1_655 . . . ? O11 Mn3 O8 C17 -154.0(3) . . . . ? O18 Mn3 O8 C17 107.7(3) 1_655 . . . ? O17 Mn3 O8 C17 -69.5(4) . . . . ? O26 Mn3 O8 C17 16.7(3) . . . . ? O8 Mn3 O11 C26 -172.3(3) . . . . ? O18 Mn3 O11 C26 -82.0(3) 1_655 . . . ? O17 Mn3 O11 C26 38.7(3) . . . . ? O26 Mn3 O11 C26 119.6(6) . . . . ? O12 Mn4 O12 C26 -162(30) 2_775 . . . ? O19 Mn4 O12 C26 70.3(4) 1_655 . . . ? O19 Mn4 O12 C26 -109.7(4) 2_675 . . . ? O17 Mn4 O12 C26 -12.4(4) . . . . ? O17 Mn4 O12 C26 167.6(4) 2_775 . . . ? O7 Mn2 O13 C19 169.0(3) . . . . ? O25 Mn2 O13 C19 -6.9(3) . . . . ? O4 Mn2 O13 C19 84.8(4) 1_655 . . . ? O2 Mn2 O13 C19 -97.7(3) . . . . ? O1 Mn2 O13 C19 -92.2(4) . . . . ? O3 Mn2 O13 C19 79.0(3) 1_655 . . . ? O11 Mn3 O17 C28 85.8(2) . . . . ? O8 Mn3 O17 C28 3.2(3) . . . . ? O18 Mn3 O17 C28 -173.5(2) 1_655 . . . ? O26 Mn3 O17 C28 -84.2(2) . . . . ? O11 Mn3 O17 Mn4 -66.53(11) . . . . ? O8 Mn3 O17 Mn4 -149.13(14) . . . . ? O18 Mn3 O17 Mn4 34.17(14) 1_655 . . . ? O26 Mn3 O17 Mn4 123.39(10) . . . . ? O12 Mn4 O17 C28 105.0(4) 2_775 . . . ? O12 Mn4 O17 C28 -75.0(4) . . . . ? O19 Mn4 O17 C28 -169.4(4) 1_655 . . . ? O19 Mn4 O17 C28 10.6(4) 2_675 . . . ? O17 Mn4 O17 C28 -88(100) 2_775 . . . ? O12 Mn4 O17 Mn3 -124.11(11) 2_775 . . . ? O12 Mn4 O17 Mn3 55.89(11) . . . . ? O19 Mn4 O17 Mn3 -38.44(11) 1_655 . . . ? O19 Mn4 O17 Mn3 141.56(11) 2_675 . . . ? O17 Mn4 O17 Mn3 43(100) 2_775 . . . ? Mn2 O2 C1 O1 10.9(4) . . . . ? Mn2 O2 C1 C2 -167.5(3) . . . . ? Mn1 O1 C1 O2 94.8(6) . . . . ? Mn2 O1 C1 O2 -10.5(4) . . . . ? Mn1 O1 C1 C2 -86.8(6) . . . . ? Mn2 O1 C1 C2 167.9(3) . . . . ? O2 C1 C2 C7 -8.2(5) . . . . ? O1 C1 C2 C7 173.4(3) . . . . ? O2 C1 C2 C3 173.4(3) . . . . ? O1 C1 C2 C3 -5.0(5) . . . . ? C7 C2 C3 C4 -1.7(5) . . . . ? C1 C2 C3 C4 176.7(3) . . . . ? C9 O5 C4 C3 -2.9(6) . . . . ? C9 O5 C4 C5 178.8(3) . . . . ? C2 C3 C4 O5 -179.6(3) . . . . ? C2 C3 C4 C5 -1.3(6) . . . . ? O5 C4 C5 C6 -179.0(3) . . . . ? C3 C4 C5 C6 2.5(6) . . . . ? C4 C5 C6 C7 -0.7(5) . . . . ? C4 C5 C6 C8 -178.5(3) . . . . ? C3 C2 C7 C6 3.5(5) . . . . ? C1 C2 C7 C6 -174.9(3) . . . . ? C5 C6 C7 C2 -2.3(5) . . . . ? C8 C6 C7 C2 175.5(3) . . . . ? Mn2 O3 C8 O4 -3.3(3) 1_455 . . . ? Mn2 O3 C8 C6 176.3(3) 1_455 . . . ? Mn1 O4 C8 O3 -125.9(5) 1_455 . . . ? Mn2 O4 C8 O3 3.4(4) 1_455 . . . ? Mn1 O4 C8 C6 54.5(7) 1_455 . . . ? Mn2 O4 C8 C6 -176.2(3) 1_455 . . . ? C5 C6 C8 O3 -161.0(3) . . . . ? C7 C6 C8 O3 21.2(5) . . . . ? C5 C6 C8 O4 18.6(5) . . . . ? C7 C6 C8 O4 -159.2(3) . . . . ? Mn2 O7 C10 O6 -11.9(6) . . . . ? Mn2 O7 C10 C11 168.3(2) . . . . ? Mn1 O6 C10 O7 26.1(6) . . . . ? Mn1 O6 C10 C11 -154.1(3) . . . . ? O7 C10 C11 C16 7.4(5) . . . . ? O6 C10 C11 C16 -172.5(3) . . . . ? O7 C10 C11 C12 -172.0(3) . . . . ? O6 C10 C11 C12 8.2(5) . . . . ? C16 C11 C12 C13 -0.4(5) . . . . ? C10 C11 C12 C13 178.9(3) . . . . ? C18 O10 C13 C14 -174.1(3) . . . . ? C18 O10 C13 C12 5.6(5) . . . . ? C11 C12 C13 O10 -176.8(3) . . . . ? C11 C12 C13 C14 2.9(5) . . . . ? O10 C13 C14 C15 176.8(3) . . . . ? C12 C13 C14 C15 -2.9(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? C13 C14 C15 C17 177.9(3) . . . . ? C12 C11 C16 C15 -2.1(5) . . . . ? C10 C11 C16 C15 178.5(3) . . . . ? C14 C15 C16 C11 2.1(5) . . . . ? C17 C15 C16 C11 -175.3(3) . . . . ? Mn3 O8 C17 O9 -14.5(5) . . . . ? Mn3 O8 C17 C15 163.9(2) . . . . ? C14 C15 C17 O9 -22.1(5) . . . . ? C16 C15 C17 O9 155.4(3) . . . . ? C14 C15 C17 O8 159.5(3) . . . . ? C16 C15 C17 O8 -23.1(5) . . . . ? Mn2 O13 C19 O14 -4.7(6) . . . . ? Mn2 O13 C19 C20 175.3(2) . . . . ? O14 C19 C20 C25 29.1(5) . . . . ? O13 C19 C20 C25 -150.9(4) . . . . ? O14 C19 C20 C21 -154.1(4) . . . . ? O13 C19 C20 C21 25.9(5) . . . . ? C25 C20 C21 C22 -1.7(5) . . . . ? C19 C20 C21 C22 -178.6(3) . . . . ? C20 C21 C22 C23 0.5(5) . . . . ? C20 C21 C22 C26 -179.2(3) . . . . ? C21 C22 C23 C24 1.3(5) . . . . ? C26 C22 C23 C24 -179.0(3) . . . . ? C27 O15 C24 C25 169.3(4) . . . . ? C27 O15 C24 C23 -11.3(6) . . . . ? C22 C23 C24 O15 178.5(3) . . . . ? C22 C23 C24 C25 -2.1(6) . . . . ? O15 C24 C25 C20 -179.6(3) . . . . ? C23 C24 C25 C20 0.9(6) . . . . ? C21 C20 C25 C24 0.9(6) . . . . ? C19 C20 C25 C24 177.7(4) . . . . ? Mn4 O12 C26 O11 -27.2(6) . . . . ? Mn4 O12 C26 C22 154.1(3) . . . . ? Mn3 O11 C26 O12 8.9(5) . . . . ? Mn3 O11 C26 C22 -172.4(2) . . . . ? C21 C22 C26 O12 163.7(3) . . . . ? C23 C22 C26 O12 -16.0(5) . . . . ? C21 C22 C26 O11 -15.1(5) . . . . ? C23 C22 C26 O11 165.2(3) . . . . ? Mn3 O17 C28 O16 -1.1(4) . . . . ? Mn4 O17 C28 O16 130.1(3) . . . . ? Mn3 O17 C28 C29 177.0(3) . . . . ? Mn4 O17 C28 C29 -51.8(5) . . . . ? O16 C28 C29 C34 -24.1(5) . . . . ? O17 C28 C29 C34 157.8(3) . . . . ? O16 C28 C29 C30 157.2(3) . . . . ? O17 C28 C29 C30 -20.9(5) . . . . ? C34 C29 C30 C31 0.5(5) . . . . ? C28 C29 C30 C31 179.2(3) . . . . ? C35 O20 C31 C30 -7.6(5) . . . . ? C35 O20 C31 C32 173.2(3) . . . . ? C29 C30 C31 O20 177.5(3) . . . . ? C29 C30 C31 C32 -3.3(5) . . . . ? O20 C31 C32 C33 -177.9(3) . . . . ? C30 C31 C32 C33 2.9(5) . . . . ? C31 C32 C33 C34 0.4(5) . . . . ? C31 C32 C33 C36 179.1(3) . . . . ? C30 C29 C34 C33 2.8(5) . . . . ? C28 C29 C34 C33 -175.9(3) . . . . ? C32 C33 C34 C29 -3.2(5) . . . . ? C36 C33 C34 C29 178.1(3) . . . . ? Mn4 O19 C36 O18 -42.8(8) 1_455 . . . ? Mn4 O19 C36 C33 139.0(5) 1_455 . . . ? Mn3 O18 C36 O19 -13.5(5) 1_455 . . . ? Mn3 O18 C36 C33 164.6(3) 1_455 . . . ? C32 C33 C36 O19 15.1(5) . . . . ? C34 C33 C36 O19 -166.2(3) . . . . ? C32 C33 C36 O18 -163.1(3) . . . . ? C34 C33 C36 O18 15.6(5) . . . . ? C39 N1 C37 C38 0.0(5) . . . . ? N1 C37 C38 N2 -0.2(5) . . . . ? C39 N2 C38 C37 0.3(5) . . . . ? C40 N2 C38 C37 -179.1(3) . . . . ? C37 N1 C39 N2 0.3(4) . . . . ? C38 N2 C39 N1 -0.4(4) . . . . ? C40 N2 C39 N1 179.1(3) . . . . ? C39 N2 C40 C41 115.3(4) . . . . ? C38 N2 C40 C41 -65.3(6) . . . . ? C44 N3 C41 C40 123.2(4) . . . . ? C42 N3 C41 C40 -60.0(6) . . . . ? N2 C40 C41 N3 -58.5(5) . . . . ? C44 N3 C42 C43 -0.1(4) . . . . ? C41 N3 C42 C43 -177.3(4) . . . . ? N3 C42 C43 N4 -0.4(5) . . . . ? C44 N4 C43 C42 0.8(5) . . . . ? C43 N4 C44 N3 -0.9(4) . . . . ? C42 N3 C44 N4 0.6(4) . . . . ? C41 N3 C44 N4 178.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O26 H12W O22 0.85 1.97 2.804(4) 168.3 1_665 O26 H11W O9 0.85 1.95 2.706(4) 147.5 . O25 H10W O23 0.85 1.87 2.700(4) 166.7 . O25 H9W O14 0.85 1.89 2.670(4) 151.1 . O24 H8W O16 0.85 2.17 3.025(5) 179.7 1_545 O24 H7W O25 0.85 2.10 2.916(4) 160.0 . O23 H6W O26 0.85 2.13 2.854(4) 143.5 1_445 O22 H3W O3 0.85 2.08 2.850(4) 150.2 . O21 H2W O24 0.85 1.97 2.792(4) 163.7 2_766 O21 H1W O9 0.85 1.95 2.766(4) 159.9 2_776 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.436 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 943592' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 Mn N4 O5' _chemical_formula_weight 487.37 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6214(10) _cell_length_b 10.0680(11) _cell_length_c 12.9326(14) _cell_angle_alpha 80.0700(10) _cell_angle_beta 81.2400(10) _cell_angle_gamma 62.3150(10) _cell_volume 1089.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3682 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 0.650 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7997 _exptl_absorpt_correction_T_max 0.8597 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8348 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4030 _reflns_number_gt 3363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0618P)^2^+0.4579P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4030 _refine_ls_number_parameters 299 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.33502(4) 0.17592(4) 1.09903(3) 0.02510(13) Uani 1 1 d . . . O1 O 0.0903(2) 0.37014(18) 1.11292(13) 0.0337(4) Uani 1 1 d . . . O2 O 0.25517(19) 0.34916(19) 1.22258(14) 0.0381(4) Uani 1 1 d . . . O3 O -0.2987(2) 0.92342(18) 1.02155(13) 0.0362(4) Uani 1 1 d . . . O4 O -0.43808(19) 1.04437(17) 1.15891(13) 0.0325(4) Uani 1 1 d . . . O5 O -0.1305(3) 0.7212(2) 1.47248(14) 0.0508(6) Uani 1 1 d . . . N1 N 0.4071(3) 0.3228(2) 0.97797(15) 0.0333(5) Uani 1 1 d . . . N2 N 0.3952(3) 0.5298(2) 0.88095(15) 0.0341(5) Uani 1 1 d . . . N3 N 0.2771(3) 0.8186(2) 0.31617(16) 0.0362(5) Uani 1 1 d U . . N4 N 0.2627(3) 1.0229(2) 0.21407(16) 0.0343(5) Uani 1 1 d U . . C1 C 0.1250(3) 0.4174(2) 1.18433(18) 0.0264(5) Uani 1 1 d . . . C2 C 0.0026(3) 0.5637(2) 1.22447(18) 0.0254(5) Uani 1 1 d . . . C3 C -0.0979(3) 0.6789(2) 1.15520(18) 0.0256(5) Uani 1 1 d . . . H3 H -0.0889 0.6662 1.0845 0.031 Uiso 1 1 calc R . . C4 C -0.2113(3) 0.8124(2) 1.19195(17) 0.0244(5) Uani 1 1 d . . . C5 C -0.2266(3) 0.8310(2) 1.29831(18) 0.0279(5) Uani 1 1 d . . . H5 H -0.3036 0.9201 1.3231 0.034 Uiso 1 1 calc R . . C6 C -0.1264(3) 0.7160(3) 1.36684(18) 0.0300(5) Uani 1 1 d . . . C7 C -0.0096(3) 0.5824(2) 1.32939(18) 0.0283(5) Uani 1 1 d . . . H7 H 0.0595 0.5065 1.3750 0.034 Uiso 1 1 calc R . . C8 C -0.3238(3) 0.9353(2) 1.11806(18) 0.0253(5) Uani 1 1 d . . . C9 C -0.2308(4) 0.8593(3) 1.5148(2) 0.0546(8) Uani 1 1 d . . . H9A H -0.2028 0.9367 1.4797 0.082 Uiso 1 1 calc R . . H9B H -0.2191 0.8468 1.5887 0.082 Uiso 1 1 calc R . . H9C H -0.3382 0.8878 1.5044 0.082 Uiso 1 1 calc R . . C10 C 0.5556(3) 0.2993(3) 0.93735(19) 0.0355(6) Uani 1 1 d . . . H10 H 0.6468 0.2097 0.9492 0.043 Uiso 1 1 calc R . . C11 C 0.5502(3) 0.4261(3) 0.87723(19) 0.0370(6) Uani 1 1 d . . . H11 H 0.6348 0.4396 0.8410 0.044 Uiso 1 1 calc R . . C12 C 0.3132(3) 0.4640(3) 0.94127(19) 0.0345(6) Uani 1 1 d . . . H12 H 0.2044 0.5109 0.9557 0.041 Uiso 1 1 calc R . . C13 C 0.3309(4) 0.6850(3) 0.8281(2) 0.0456(7) Uani 1 1 d . . . H13A H 0.3939 0.7322 0.8405 0.055 Uiso 1 1 calc R . . H13B H 0.2243 0.7426 0.8579 0.055 Uiso 1 1 calc R . . C14 C 0.3299(3) 0.6888(3) 0.71036(19) 0.0360(6) Uani 1 1 d . . . C15 C 0.2290(4) 0.6497(4) 0.6723(2) 0.0487(7) Uani 1 1 d . . . H15 H 0.1585 0.6252 0.7190 0.058 Uiso 1 1 calc R . . C16 C 0.2315(4) 0.6466(4) 0.5650(2) 0.0475(7) Uani 1 1 d . . . H16 H 0.1621 0.6211 0.5403 0.057 Uiso 1 1 calc R . . C17 C 0.3356(3) 0.6807(3) 0.49558(19) 0.0355(6) Uani 1 1 d . . . C18 C 0.4368(4) 0.7191(3) 0.5338(2) 0.0434(7) Uani 1 1 d . . . H18 H 0.5081 0.7423 0.4871 0.052 Uiso 1 1 calc R . . C19 C 0.4340(3) 0.7236(3) 0.6404(2) 0.0418(6) Uani 1 1 d . . . H19 H 0.5026 0.7503 0.6648 0.050 Uiso 1 1 calc R . . C20 C 0.3447(4) 0.6702(3) 0.3791(2) 0.0439(7) Uani 1 1 d . . . H20A H 0.4541 0.6142 0.3537 0.053 Uiso 1 1 calc R . . H20B H 0.2892 0.6145 0.3692 0.053 Uiso 1 1 calc R . . C21 C 0.3540(3) 0.8955(3) 0.26734(19) 0.0348(6) Uani 1 1 d U . . H21 H 0.4611 0.8625 0.2706 0.042 Uiso 1 1 calc R . . C22 C 0.1212(4) 1.0266(4) 0.2300(3) 0.0772(12) Uani 1 1 d U . . H22 H 0.0306 1.1044 0.2024 0.093 Uiso 1 1 calc R . . C23 C 0.1273(4) 0.9009(5) 0.2924(3) 0.0831(13) Uani 1 1 d U . . H23 H 0.0442 0.8769 0.3142 0.100 Uiso 1 1 calc 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 Mn1 0.0272(2) 0.01811(19) 0.0222(2) 0.00053(13) -0.00439(14) -0.00391(14) O1 0.0339(9) 0.0254(8) 0.0338(9) -0.0070(7) -0.0066(7) -0.0044(7) O2 0.0267(9) 0.0315(9) 0.0433(10) -0.0069(8) -0.0097(8) 0.0004(7) O3 0.0492(11) 0.0274(9) 0.0257(9) -0.0003(7) -0.0116(8) -0.0104(8) O4 0.0275(9) 0.0238(8) 0.0339(9) -0.0012(7) -0.0075(7) -0.0007(7) O5 0.0654(13) 0.0364(10) 0.0269(9) -0.0085(8) -0.0160(9) 0.0021(9) N1 0.0402(12) 0.0290(11) 0.0282(11) 0.0033(8) -0.0060(9) -0.0148(9) N2 0.0512(14) 0.0292(11) 0.0228(10) 0.0026(8) -0.0071(9) -0.0197(10) N3 0.0434(12) 0.0323(11) 0.0305(11) 0.0060(9) -0.0053(9) -0.0177(10) N4 0.0384(12) 0.0294(11) 0.0294(11) 0.0026(8) -0.0027(9) -0.0127(9) C1 0.0268(12) 0.0205(11) 0.0261(12) 0.0014(9) -0.0003(9) -0.0079(10) C2 0.0238(11) 0.0198(11) 0.0289(12) -0.0017(9) -0.0034(9) -0.0066(9) C3 0.0262(12) 0.0236(11) 0.0223(11) -0.0019(9) -0.0044(9) -0.0067(9) C4 0.0255(11) 0.0194(10) 0.0255(12) 0.0002(9) -0.0056(9) -0.0075(9) C5 0.0263(12) 0.0203(11) 0.0296(12) -0.0049(9) -0.0044(9) -0.0029(9) C6 0.0332(13) 0.0277(12) 0.0242(12) -0.0025(9) -0.0067(10) -0.0086(10) C7 0.0280(12) 0.0220(11) 0.0287(12) 0.0023(9) -0.0090(10) -0.0059(10) C8 0.0264(12) 0.0197(11) 0.0287(12) 0.0002(9) -0.0073(9) -0.0091(9) C9 0.067(2) 0.0479(17) 0.0330(15) -0.0178(13) -0.0056(14) -0.0074(15) C10 0.0397(15) 0.0343(14) 0.0280(13) -0.0015(11) -0.0050(11) -0.0129(12) C11 0.0433(15) 0.0442(15) 0.0264(13) -0.0022(11) -0.0004(11) -0.0236(13) C12 0.0395(14) 0.0314(13) 0.0296(13) 0.0018(10) -0.0043(11) -0.0148(11) C13 0.075(2) 0.0275(13) 0.0330(14) 0.0042(11) -0.0111(14) -0.0229(14) C14 0.0504(16) 0.0270(12) 0.0283(13) 0.0047(10) -0.0088(11) -0.0164(12) C15 0.0540(18) 0.068(2) 0.0343(15) 0.0011(14) 0.0001(13) -0.0390(16) C16 0.0528(18) 0.0620(19) 0.0397(16) 0.0000(14) -0.0095(13) -0.0361(16) C17 0.0484(16) 0.0264(12) 0.0287(13) 0.0052(10) -0.0080(11) -0.0156(11) C18 0.0540(17) 0.0446(16) 0.0365(15) 0.0071(12) -0.0007(13) -0.0312(14) C19 0.0545(17) 0.0405(15) 0.0394(15) 0.0072(12) -0.0136(13) -0.0300(14) C20 0.0663(19) 0.0313(14) 0.0306(14) 0.0053(11) -0.0081(13) -0.0207(14) C21 0.0362(13) 0.0349(13) 0.0307(13) 0.0041(10) -0.0069(10) -0.0153(11) C22 0.0386(17) 0.069(2) 0.101(3) 0.044(2) -0.0190(17) -0.0195(16) C23 0.0472(19) 0.081(2) 0.112(3) 0.046(2) -0.0166(19) -0.0369(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 2.1410(17) 2_567 ? Mn1 O4 2.1434(16) 1_645 ? Mn1 N1 2.223(2) . ? Mn1 N4 2.228(2) 1_546 ? Mn1 O1 2.2611(16) . ? Mn1 O2 2.3511(17) . ? Mn1 C1 2.626(2) . ? O1 C1 1.258(3) . ? O2 C1 1.248(3) . ? O3 C8 1.250(3) . ? O3 Mn1 2.1410(17) 2_567 ? O4 C8 1.263(3) . ? O4 Mn1 2.1434(16) 1_465 ? O5 C6 1.370(3) . ? O5 C9 1.421(3) . ? N1 C12 1.329(3) . ? N1 C10 1.369(3) . ? N2 C12 1.338(3) . ? N2 C11 1.366(3) . ? N2 C13 1.468(3) . ? N3 C21 1.329(3) . ? N3 C23 1.340(4) . ? N3 C20 1.468(3) . ? N4 C21 1.313(3) . ? N4 C22 1.329(4) . ? N4 Mn1 2.228(2) 1_564 ? C1 C2 1.514(3) . ? C2 C7 1.382(3) . ? C2 C3 1.395(3) . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 C8 1.510(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C7 1.401(3) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.358(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.518(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.373(4) . ? C14 C15 1.381(4) . ? C15 C16 1.389(4) . ? C15 H15 0.9300 . ? C16 C17 1.367(4) . ? C16 H16 0.9300 . ? C17 C18 1.380(4) . ? C17 C20 1.515(3) . ? C18 C19 1.383(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21 0.9300 . ? C22 C23 1.360(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O4 112.87(7) 2_567 1_645 ? O3 Mn1 N1 90.63(7) 2_567 . ? O4 Mn1 N1 95.63(7) 1_645 . ? O3 Mn1 N4 86.60(7) 2_567 1_546 ? O4 Mn1 N4 85.13(7) 1_645 1_546 ? N1 Mn1 N4 177.21(7) . 1_546 ? O3 Mn1 O1 97.64(6) 2_567 . ? O4 Mn1 O1 149.03(6) 1_645 . ? N1 Mn1 O1 88.99(7) . . ? N4 Mn1 O1 91.74(7) 1_546 . ? O3 Mn1 O2 154.44(7) 2_567 . ? O4 Mn1 O2 92.27(6) 1_645 . ? N1 Mn1 O2 91.44(7) . . ? N4 Mn1 O2 91.21(7) 1_546 . ? O1 Mn1 O2 56.95(6) . . ? O3 Mn1 C1 126.25(7) 2_567 . ? O4 Mn1 C1 120.63(7) 1_645 . ? N1 Mn1 C1 89.16(7) . . ? N4 Mn1 C1 92.77(7) 1_546 . ? O1 Mn1 C1 28.62(7) . . ? O2 Mn1 C1 28.37(7) . . ? C1 O1 Mn1 91.99(13) . . ? C1 O2 Mn1 88.13(14) . . ? C8 O3 Mn1 143.23(17) . 2_567 ? C8 O4 Mn1 125.79(15) . 1_465 ? C6 O5 C9 118.8(2) . . ? C12 N1 C10 105.2(2) . . ? C12 N1 Mn1 125.51(17) . . ? C10 N1 Mn1 128.69(16) . . ? C12 N2 C11 107.5(2) . . ? C12 N2 C13 126.5(2) . . ? C11 N2 C13 126.0(2) . . ? C21 N3 C23 106.0(2) . . ? C21 N3 C20 126.7(2) . . ? C23 N3 C20 127.2(3) . . ? C21 N4 C22 104.3(2) . . ? C21 N4 Mn1 127.70(18) . 1_564 ? C22 N4 Mn1 127.05(19) . 1_564 ? O2 C1 O1 122.8(2) . . ? O2 C1 C2 119.2(2) . . ? O1 C1 C2 118.0(2) . . ? O2 C1 Mn1 63.51(12) . . ? O1 C1 Mn1 59.39(11) . . ? C2 C1 Mn1 175.26(16) . . ? C7 C2 C3 120.3(2) . . ? C7 C2 C1 120.0(2) . . ? C3 C2 C1 119.7(2) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 C8 120.0(2) . . ? C5 C4 C8 119.70(19) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? O5 C6 C5 124.9(2) . . ? O5 C6 C7 114.9(2) . . ? C5 C6 C7 120.2(2) . . ? C2 C7 C6 119.7(2) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? O3 C8 O4 124.3(2) . . ? O3 C8 C4 118.69(19) . . ? O4 C8 C4 117.0(2) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N1 110.0(2) . . ? C11 C10 H10 125.0 . . ? N1 C10 H10 125.0 . . ? C10 C11 N2 106.0(2) . . ? C10 C11 H11 127.0 . . ? N2 C11 H11 127.0 . . ? N1 C12 N2 111.3(2) . . ? N1 C12 H12 124.3 . . ? N2 C12 H12 124.3 . . ? N2 C13 C14 111.5(2) . . ? N2 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? N2 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C19 C14 C15 118.9(2) . . ? C19 C14 C13 120.8(3) . . ? C15 C14 C13 120.2(3) . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 118.9(2) . . ? C16 C17 C20 120.6(3) . . ? C18 C17 C20 120.4(3) . . ? C17 C18 C19 121.1(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C14 C19 C18 120.1(3) . . ? C14 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? N3 C20 C17 113.0(2) . . ? N3 C20 H20A 109.0 . . ? C17 C20 H20A 109.0 . . ? N3 C20 H20B 109.0 . . ? C17 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? N4 C21 N3 112.8(2) . . ? N4 C21 H21 123.6 . . ? N3 C21 H21 123.6 . . ? N4 C22 C23 110.6(3) . . ? N4 C22 H22 124.7 . . ? C23 C22 H22 124.7 . . ? N3 C23 C22 106.2(3) . . ? N3 C23 H23 126.9 . . ? C22 C23 H23 126.9 . . ? 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 O3 Mn1 O1 C1 179.40(14) 2_567 . . . ? O4 Mn1 O1 C1 9.2(2) 1_645 . . . ? N1 Mn1 O1 C1 -90.10(14) . . . . ? N4 Mn1 O1 C1 92.60(14) 1_546 . . . ? O2 Mn1 O1 C1 2.28(13) . . . . ? O3 Mn1 O2 C1 -8.9(2) 2_567 . . . ? O4 Mn1 O2 C1 -178.76(14) 1_645 . . . ? N1 Mn1 O2 C1 85.55(15) . . . . ? N4 Mn1 O2 C1 -93.59(15) 1_546 . . . ? O1 Mn1 O2 C1 -2.30(13) . . . . ? O3 Mn1 N1 C12 95.4(2) 2_567 . . . ? O4 Mn1 N1 C12 -151.5(2) 1_645 . . . ? N4 Mn1 N1 C12 102.8(15) 1_546 . . . ? O1 Mn1 N1 C12 -2.2(2) . . . . ? O2 Mn1 N1 C12 -59.1(2) . . . . ? C1 Mn1 N1 C12 -30.8(2) . . . . ? O3 Mn1 N1 C10 -95.2(2) 2_567 . . . ? O4 Mn1 N1 C10 17.9(2) 1_645 . . . ? N4 Mn1 N1 C10 -87.8(16) 1_546 . . . ? O1 Mn1 N1 C10 167.2(2) . . . . ? O2 Mn1 N1 C10 110.3(2) . . . . ? C1 Mn1 N1 C10 138.6(2) . . . . ? Mn1 O2 C1 O1 4.1(2) . . . . ? Mn1 O2 C1 C2 -175.62(19) . . . . ? Mn1 O1 C1 O2 -4.3(2) . . . . ? Mn1 O1 C1 C2 175.46(18) . . . . ? O3 Mn1 C1 O2 175.23(13) 2_567 . . . ? O4 Mn1 C1 O2 1.44(17) 1_645 . . . ? N1 Mn1 C1 O2 -94.60(15) . . . . ? N4 Mn1 C1 O2 87.42(15) 1_546 . . . ? O1 Mn1 C1 O2 176.0(2) . . . . ? O3 Mn1 C1 O1 -0.74(17) 2_567 . . . ? O4 Mn1 C1 O1 -174.53(13) 1_645 . . . ? N1 Mn1 C1 O1 89.43(14) . . . . ? N4 Mn1 C1 O1 -88.55(14) 1_546 . . . ? O2 Mn1 C1 O1 -176.0(2) . . . . ? O3 Mn1 C1 C2 -59(2) 2_567 . . . ? O4 Mn1 C1 C2 128(2) 1_645 . . . ? N1 Mn1 C1 C2 32(2) . . . . ? N4 Mn1 C1 C2 -146(2) 1_546 . . . ? O1 Mn1 C1 C2 -58(2) . . . . ? O2 Mn1 C1 C2 126(2) . . . . ? O2 C1 C2 C7 -35.0(3) . . . . ? O1 C1 C2 C7 145.2(2) . . . . ? Mn1 C1 C2 C7 -159.1(19) . . . . ? O2 C1 C2 C3 145.3(2) . . . . ? O1 C1 C2 C3 -34.4(3) . . . . ? Mn1 C1 C2 C3 21(2) . . . . ? C7 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 179.2(2) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C2 C3 C4 C8 -178.0(2) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C8 C4 C5 C6 177.9(2) . . . . ? C9 O5 C6 C5 -7.9(4) . . . . ? C9 O5 C6 C7 171.7(3) . . . . ? C4 C5 C6 O5 -179.8(2) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? C3 C2 C7 C6 1.8(4) . . . . ? C1 C2 C7 C6 -177.9(2) . . . . ? O5 C6 C7 C2 178.5(2) . . . . ? C5 C6 C7 C2 -1.9(4) . . . . ? Mn1 O3 C8 O4 -95.9(3) 2_567 . . . ? Mn1 O3 C8 C4 84.3(3) 2_567 . . . ? Mn1 O4 C8 O3 30.2(3) 1_465 . . . ? Mn1 O4 C8 C4 -149.95(16) 1_465 . . . ? C3 C4 C8 O3 -10.0(3) . . . . ? C5 C4 C8 O3 172.9(2) . . . . ? C3 C4 C8 O4 170.1(2) . . . . ? C5 C4 C8 O4 -7.0(3) . . . . ? C12 N1 C10 C11 0.3(3) . . . . ? Mn1 N1 C10 C11 -170.76(17) . . . . ? N1 C10 C11 N2 0.0(3) . . . . ? C12 N2 C11 C10 -0.3(3) . . . . ? C13 N2 C11 C10 179.7(2) . . . . ? C10 N1 C12 N2 -0.6(3) . . . . ? Mn1 N1 C12 N2 170.90(15) . . . . ? C11 N2 C12 N1 0.6(3) . . . . ? C13 N2 C12 N1 -179.5(2) . . . . ? C12 N2 C13 C14 -105.8(3) . . . . ? C11 N2 C13 C14 74.2(3) . . . . ? N2 C13 C14 C19 -107.8(3) . . . . ? N2 C13 C14 C15 69.0(4) . . . . ? C19 C14 C15 C16 -0.4(4) . . . . ? C13 C14 C15 C16 -177.3(3) . . . . ? C14 C15 C16 C17 0.7(5) . . . . ? C15 C16 C17 C18 -0.4(4) . . . . ? C15 C16 C17 C20 177.0(3) . . . . ? C16 C17 C18 C19 -0.1(4) . . . . ? C20 C17 C18 C19 -177.5(3) . . . . ? C15 C14 C19 C18 -0.1(4) . . . . ? C13 C14 C19 C18 176.8(3) . . . . ? C17 C18 C19 C14 0.4(4) . . . . ? C21 N3 C20 C17 93.5(3) . . . . ? C23 N3 C20 C17 -89.7(4) . . . . ? C16 C17 C20 N3 107.2(3) . . . . ? C18 C17 C20 N3 -75.4(3) . . . . ? C22 N4 C21 N3 0.0(3) . . . . ? Mn1 N4 C21 N3 -169.58(16) 1_564 . . . ? C23 N3 C21 N4 0.4(4) . . . . ? C20 N3 C21 N4 177.8(2) . . . . ? C21 N4 C22 C23 -0.4(5) . . . . ? Mn1 N4 C22 C23 169.3(3) 1_564 . . . ? C21 N3 C23 C22 -0.6(5) . . . . ? C20 N3 C23 C22 -178.0(3) . . . . ? N4 C22 C23 N3 0.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.889 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 943593' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H24 Mn N4 O5' _chemical_formula_weight 539.44 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.564(4) _cell_length_b 18.302(4) _cell_length_c 15.879(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4813.6(18) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1151 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 17.48 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2232 _exptl_absorpt_coefficient_mu 0.596 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8702 _exptl_absorpt_correction_T_max 0.9651 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28054 _diffrn_reflns_av_R_equivalents 0.1364 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4484 _reflns_number_gt 2367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0526P)^2^+0.9366P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4484 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1346 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 1.04019(3) 0.22421(4) 0.37654(4) 0.0353(2) Uani 1 1 d . . . O1 O 0.90001(16) 0.20761(16) 0.24083(18) 0.0467(8) Uani 1 1 d . . . O2 O 0.91118(16) 0.23430(16) 0.37684(19) 0.0453(8) Uani 1 1 d . . . O3 O 0.66124(16) 0.27227(17) 0.54668(19) 0.0467(8) Uani 1 1 d . . . O4 O 0.54318(16) 0.26183(17) 0.48497(18) 0.0480(8) Uani 1 1 d . . . O5 O 0.59952(16) 0.21940(18) 0.18216(18) 0.0548(9) Uani 1 1 d . . . N1 N 0.5570(2) -0.1563(2) 0.1465(2) 0.0461(10) Uani 1 1 d . . . N2 N 0.6279(2) -0.0585(2) 0.1870(2) 0.0474(10) Uani 1 1 d . . . N3 N 1.0303(2) 0.1011(2) 0.3802(2) 0.0493(10) Uani 1 1 d . . . N4 N 0.9634(2) -0.0027(2) 0.3572(2) 0.0487(11) Uani 1 1 d . . . C1 C 0.8708(2) 0.2243(2) 0.3101(3) 0.0364(10) Uani 1 1 d . . . C2 C 0.7799(2) 0.2306(2) 0.3168(3) 0.0324(10) Uani 1 1 d . . . C3 C 0.7340(2) 0.2210(2) 0.2444(3) 0.0366(10) Uani 1 1 d . . . H3 H 0.7590 0.2112 0.1932 0.044 Uiso 1 1 calc R . . C4 C 0.6503(2) 0.2261(2) 0.2493(3) 0.0375(10) Uani 1 1 d . . . C5 C 0.6139(2) 0.2392(2) 0.3266(3) 0.0383(11) Uani 1 1 d . . . H5 H 0.5579 0.2418 0.3299 0.046 Uiso 1 1 calc R . . C6 C 0.6594(2) 0.2485(2) 0.3987(3) 0.0346(11) Uani 1 1 d . . . C7 C 0.7431(2) 0.2447(2) 0.3936(3) 0.0351(11) Uani 1 1 d . . . H7 H 0.7744 0.2516 0.4416 0.042 Uiso 1 1 calc R . . C8 C 0.6188(3) 0.2620(2) 0.4821(3) 0.0367(11) Uani 1 1 d . . . C9 C 0.6349(3) 0.2118(3) 0.1008(3) 0.0570(14) Uani 1 1 d . . . H9A H 0.6712 0.2518 0.0909 0.085 Uiso 1 1 calc R . . H9B H 0.5932 0.2121 0.0588 0.085 Uiso 1 1 calc R . . H9C H 0.6641 0.1666 0.0980 0.085 Uiso 1 1 calc R . . C10 C 1.0758(3) 0.0431(3) 0.4101(3) 0.0431(12) Uani 1 1 d . . . C11 C 1.1511(3) 0.0429(3) 0.4481(3) 0.0522(13) Uani 1 1 d . . . H11 H 1.1797 0.0860 0.4566 0.063 Uiso 1 1 calc R . . C12 C 1.1821(3) -0.0241(3) 0.4727(3) 0.0698(16) Uani 1 1 d . . . H12 H 1.2329 -0.0262 0.4976 0.084 Uiso 1 1 calc R . . C13 C 1.1387(3) -0.0879(3) 0.4610(4) 0.0764(17) Uani 1 1 d . . . H13 H 1.1608 -0.1317 0.4798 0.092 Uiso 1 1 calc R . . C14 C 1.0638(3) -0.0892(3) 0.4225(3) 0.0580(14) Uani 1 1 d . . . H14 H 1.0351 -0.1323 0.4143 0.070 Uiso 1 1 calc R . . C15 C 1.0347(3) -0.0226(3) 0.3971(3) 0.0421(11) Uani 1 1 d . . . C16 C 0.9652(3) 0.0702(3) 0.3491(3) 0.0556(14) Uani 1 1 d . . . H16 H 0.9239 0.0966 0.3236 0.067 Uiso 1 1 calc R . . C17 C 0.8986(3) -0.0518(3) 0.3284(3) 0.0538(13) Uani 1 1 d . . . H17A H 0.8803 -0.0814 0.3754 0.065 Uiso 1 1 calc R . . H17B H 0.9198 -0.0845 0.2857 0.065 Uiso 1 1 calc R . . C18 C 0.8276(3) -0.0099(3) 0.2924(3) 0.0559(14) Uani 1 1 d . . . H18A H 0.8464 0.0208 0.2467 0.067 Uiso 1 1 calc R . . H18B H 0.8055 0.0216 0.3357 0.067 Uiso 1 1 calc R . . C19 C 0.7610(3) -0.0600(3) 0.2597(3) 0.0538(13) Uani 1 1 d . . . H19A H 0.7826 -0.0923 0.2168 0.065 Uiso 1 1 calc R . . H19B H 0.7403 -0.0897 0.3054 0.065 Uiso 1 1 calc R . . C20 C 0.6934(3) -0.0141(3) 0.2228(3) 0.0552(14) Uani 1 1 d . . . H20A H 0.6714 0.0171 0.2665 0.066 Uiso 1 1 calc R . . H20B H 0.7153 0.0171 0.1791 0.066 Uiso 1 1 calc R . . C21 C 0.5563(3) -0.0323(3) 0.1539(3) 0.0450(12) Uani 1 1 d . . . C22 C 0.5272(3) 0.0375(3) 0.1437(3) 0.0642(15) Uani 1 1 d . . . H22 H 0.5560 0.0782 0.1619 0.077 Uiso 1 1 calc R . . C23 C 0.4533(4) 0.0442(3) 0.1052(4) 0.0766(18) Uani 1 1 d . . . H23 H 0.4321 0.0905 0.0962 0.092 Uiso 1 1 calc R . . C24 C 0.4096(3) -0.0164(4) 0.0794(3) 0.0718(17) Uani 1 1 d . . . H24 H 0.3598 -0.0096 0.0534 0.086 Uiso 1 1 calc R . . C25 C 0.4378(3) -0.0863(3) 0.0913(3) 0.0581(14) Uani 1 1 d . . . H25 H 0.4078 -0.1269 0.0749 0.070 Uiso 1 1 calc R . . C26 C 0.5128(3) -0.0936(2) 0.1289(3) 0.0425(11) Uani 1 1 d . . . C27 C 0.6241(3) -0.1317(3) 0.1802(3) 0.0513(13) Uani 1 1 d . . . H27 H 0.6656 -0.1624 0.1980 0.062 Uiso 1 1 calc 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 Mn1 0.0273(3) 0.0427(4) 0.0358(4) 0.0002(3) 0.0001(3) -0.0056(3) O1 0.0343(16) 0.067(2) 0.039(2) 0.0050(16) 0.0083(15) 0.0068(15) O2 0.0307(15) 0.065(2) 0.0401(19) -0.0004(17) -0.0032(15) -0.0033(15) O3 0.0367(17) 0.064(2) 0.039(2) -0.0093(17) 0.0006(14) 0.0015(16) O4 0.0287(16) 0.075(2) 0.0400(19) -0.0021(16) 0.0041(14) 0.0077(15) O5 0.0338(17) 0.096(3) 0.034(2) -0.0073(18) -0.0055(14) 0.0004(17) N1 0.040(2) 0.043(2) 0.055(3) -0.0012(19) -0.0061(18) -0.0015(18) N2 0.048(2) 0.045(3) 0.050(3) -0.002(2) -0.002(2) -0.007(2) N3 0.044(2) 0.043(2) 0.061(3) 0.002(2) -0.006(2) -0.0102(19) N4 0.045(2) 0.039(2) 0.062(3) 0.001(2) -0.001(2) -0.011(2) C1 0.033(2) 0.035(3) 0.041(3) 0.010(2) 0.003(2) 0.001(2) C2 0.029(2) 0.034(3) 0.034(3) 0.003(2) 0.0004(18) -0.0012(19) C3 0.032(2) 0.045(3) 0.032(3) 0.003(2) 0.0040(19) -0.003(2) C4 0.033(2) 0.048(3) 0.032(3) 0.000(2) -0.002(2) -0.003(2) C5 0.025(2) 0.050(3) 0.040(3) -0.001(2) 0.000(2) 0.001(2) C6 0.032(2) 0.039(3) 0.033(3) 0.004(2) 0.0015(19) 0.0033(18) C7 0.033(2) 0.039(3) 0.034(3) 0.000(2) -0.0028(19) 0.0007(19) C8 0.034(3) 0.041(3) 0.034(3) 0.002(2) 0.001(2) 0.005(2) C9 0.050(3) 0.086(4) 0.035(3) -0.007(3) -0.004(2) 0.006(3) C10 0.038(3) 0.050(3) 0.041(3) -0.001(2) 0.004(2) -0.004(2) C11 0.050(3) 0.058(4) 0.048(3) -0.003(3) -0.001(2) -0.010(3) C12 0.062(4) 0.079(4) 0.068(4) 0.001(3) -0.015(3) 0.005(3) C13 0.077(4) 0.068(4) 0.085(5) 0.009(4) -0.024(3) 0.007(3) C14 0.069(4) 0.047(3) 0.058(3) 0.007(3) 0.002(3) -0.005(3) C15 0.044(3) 0.045(3) 0.037(3) 0.005(2) 0.005(2) -0.005(2) C16 0.052(3) 0.043(3) 0.071(4) 0.000(3) -0.010(3) -0.004(3) C17 0.053(3) 0.048(3) 0.061(4) -0.007(3) -0.008(3) -0.017(2) C18 0.056(3) 0.059(3) 0.053(3) -0.002(3) 0.002(3) -0.019(3) C19 0.052(3) 0.051(3) 0.059(3) -0.005(3) 0.001(3) -0.016(3) C20 0.051(3) 0.047(3) 0.068(4) -0.007(3) 0.003(3) -0.014(2) C21 0.050(3) 0.042(3) 0.044(3) 0.001(2) 0.011(2) 0.003(2) C22 0.078(4) 0.050(3) 0.064(4) 0.005(3) 0.016(3) 0.004(3) C23 0.082(4) 0.069(4) 0.079(5) 0.015(4) 0.000(4) 0.028(4) C24 0.061(4) 0.090(5) 0.064(4) 0.002(4) -0.010(3) 0.023(4) C25 0.052(3) 0.072(4) 0.050(3) -0.001(3) -0.005(2) 0.013(3) C26 0.046(3) 0.042(3) 0.039(3) -0.001(2) 0.002(2) 0.001(2) C27 0.045(3) 0.047(3) 0.062(4) -0.001(3) -0.005(2) 0.001(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 O1 2.132(3) 3_755 ? Mn1 O2 2.145(3) . ? Mn1 O4 2.214(3) 4_556 ? Mn1 N1 2.235(4) 6_666 ? Mn1 N3 2.259(4) . ? Mn1 O3 2.347(3) 4_556 ? Mn1 C8 2.608(4) 4_556 ? O1 C1 1.240(5) . ? O1 Mn1 2.132(3) 3_755 ? O2 C1 1.265(5) . ? O3 C8 1.258(5) . ? O3 Mn1 2.347(3) 4_456 ? O4 C8 1.254(5) . ? O4 Mn1 2.214(3) 4_456 ? O5 C4 1.364(4) . ? O5 C9 1.425(5) . ? N1 C27 1.313(5) . ? N1 C26 1.390(5) . ? N1 Mn1 2.235(4) 6_556 ? N2 C27 1.346(5) . ? N2 C21 1.384(5) . ? N2 C20 1.469(5) . ? N3 C16 1.315(5) . ? N3 C10 1.386(5) . ? N4 C16 1.341(6) . ? N4 C15 1.389(5) . ? N4 C17 1.473(5) . ? C1 C2 1.515(5) . ? C2 C3 1.389(5) . ? C2 C7 1.386(5) . ? C3 C4 1.393(5) . ? C3 H3 0.9300 . ? C4 C5 1.388(5) . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 C7 1.391(5) . ? C6 C8 1.505(6) . ? C7 H7 0.9300 . ? C8 Mn1 2.608(4) 4_456 ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.387(6) . ? C10 C15 1.396(6) . ? C11 C12 1.386(6) . ? C11 H11 0.9300 . ? C12 C13 1.385(7) . ? C12 H12 0.9300 . ? C13 C14 1.384(6) . ? C13 H13 0.9300 . ? C14 C15 1.370(6) . ? C14 H14 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.516(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.525(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.517(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.376(7) . ? C21 C26 1.392(6) . ? C22 C23 1.373(7) . ? C22 H22 0.9300 . ? C23 C24 1.386(7) . ? C23 H23 0.9300 . ? C24 C25 1.375(7) . ? C24 H24 0.9300 . ? C25 C26 1.384(6) . ? C25 H25 0.9300 . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O2 118.49(11) 3_755 . ? O1 Mn1 O4 150.93(11) 3_755 4_556 ? O2 Mn1 O4 90.58(11) . 4_556 ? O1 Mn1 N1 86.46(13) 3_755 6_666 ? O2 Mn1 N1 92.32(12) . 6_666 ? O4 Mn1 N1 92.68(12) 4_556 6_666 ? O1 Mn1 N3 85.06(13) 3_755 . ? O2 Mn1 N3 90.80(12) . . ? O4 Mn1 N3 95.24(13) 4_556 . ? N1 Mn1 N3 171.45(14) 6_666 . ? O1 Mn1 O3 93.50(10) 3_755 4_556 ? O2 Mn1 O3 147.93(11) . 4_556 ? O4 Mn1 O3 57.45(10) 4_556 4_556 ? N1 Mn1 O3 87.22(12) 6_666 4_556 ? N3 Mn1 O3 94.35(12) . 4_556 ? O1 Mn1 C8 122.30(12) 3_755 4_556 ? O2 Mn1 C8 119.16(13) . 4_556 ? O4 Mn1 C8 28.68(11) 4_556 4_556 ? N1 Mn1 C8 89.07(13) 6_666 4_556 ? N3 Mn1 C8 96.35(14) . 4_556 ? O3 Mn1 C8 28.80(11) 4_556 4_556 ? C1 O1 Mn1 157.2(3) . 3_755 ? C1 O2 Mn1 120.8(3) . . ? C8 O3 Mn1 87.2(2) . 4_456 ? C8 O4 Mn1 93.4(3) . 4_456 ? C4 O5 C9 117.6(3) . . ? C27 N1 C26 104.2(4) . . ? C27 N1 Mn1 120.5(3) . 6_556 ? C26 N1 Mn1 135.1(3) . 6_556 ? C27 N2 C21 106.0(4) . . ? C27 N2 C20 128.0(4) . . ? C21 N2 C20 126.0(4) . . ? C16 N3 C10 104.1(4) . . ? C16 N3 Mn1 118.6(3) . . ? C10 N3 Mn1 137.2(3) . . ? C16 N4 C15 106.6(4) . . ? C16 N4 C17 126.4(4) . . ? C15 N4 C17 127.0(4) . . ? O1 C1 O2 124.9(4) . . ? O1 C1 C2 117.9(4) . . ? O2 C1 C2 117.1(4) . . ? C3 C2 C7 120.7(4) . . ? C3 C2 C1 118.4(4) . . ? C7 C2 C1 120.9(4) . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? O5 C4 C5 116.1(3) . . ? O5 C4 C3 124.4(4) . . ? C5 C4 C3 119.5(4) . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.3(4) . . ? C5 C6 C8 120.4(4) . . ? C7 C6 C8 120.3(4) . . ? C6 C7 C2 119.9(4) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? O4 C8 O3 121.9(4) . . ? O4 C8 C6 118.6(4) . . ? O3 C8 C6 119.5(4) . . ? O4 C8 Mn1 58.0(2) . 4_456 ? O3 C8 Mn1 64.0(2) . 4_456 ? C6 C8 Mn1 175.0(3) . 4_456 ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 C11 129.7(4) . . ? N3 C10 C15 110.2(4) . . ? C11 C10 C15 120.1(5) . . ? C12 C11 C10 117.2(5) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? C11 C12 C13 121.1(5) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 122.6(5) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C15 C14 C13 115.5(5) . . ? C15 C14 H14 122.2 . . ? C13 C14 H14 122.2 . . ? C14 C15 N4 131.8(4) . . ? C14 C15 C10 123.4(4) . . ? N4 C15 C10 104.8(4) . . ? N3 C16 N4 114.2(4) . . ? N3 C16 H16 122.9 . . ? N4 C16 H16 122.9 . . ? N4 C17 C18 112.0(4) . . ? N4 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N4 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C19 112.7(4) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 109.5(4) . . ? C20 C19 H19A 109.8 . . ? C18 C19 H19A 109.8 . . ? C20 C19 H19B 109.8 . . ? C18 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? N2 C20 C19 112.8(4) . . ? N2 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? N2 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 N2 131.9(5) . . ? C22 C21 C26 122.3(5) . . ? N2 C21 C26 105.8(4) . . ? C23 C22 C21 116.5(5) . . ? C23 C22 H22 121.7 . . ? C21 C22 H22 121.7 . . ? C22 C23 C24 121.8(5) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C25 C24 C23 121.7(5) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C24 C25 C26 117.0(5) . . ? C24 C25 H25 121.5 . . ? C26 C25 H25 121.5 . . ? C25 C26 N1 129.8(4) . . ? C25 C26 C21 120.6(4) . . ? N1 C26 C21 109.6(4) . . ? N1 C27 N2 114.4(4) . . ? N1 C27 H27 122.8 . . ? N2 C27 H27 122.8 . . ? 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 O2 C1 6.1(4) 3_755 . . . ? O4 Mn1 O2 C1 -173.9(3) 4_556 . . . ? N1 Mn1 O2 C1 93.4(3) 6_666 . . . ? N3 Mn1 O2 C1 -78.7(3) . . . . ? O3 Mn1 O2 C1 -178.2(3) 4_556 . . . ? C8 Mn1 O2 C1 -176.4(3) 4_556 . . . ? O1 Mn1 N3 C16 -92.2(4) 3_755 . . . ? O2 Mn1 N3 C16 26.4(4) . . . . ? O4 Mn1 N3 C16 117.0(4) 4_556 . . . ? N1 Mn1 N3 C16 -85.0(10) 6_666 . . . ? O3 Mn1 N3 C16 174.7(4) 4_556 . . . ? C8 Mn1 N3 C16 145.8(4) 4_556 . . . ? O1 Mn1 N3 C10 90.1(4) 3_755 . . . ? O2 Mn1 N3 C10 -151.3(4) . . . . ? O4 Mn1 N3 C10 -60.7(4) 4_556 . . . ? N1 Mn1 N3 C10 97.3(10) 6_666 . . . ? O3 Mn1 N3 C10 -3.0(5) 4_556 . . . ? C8 Mn1 N3 C10 -31.9(5) 4_556 . . . ? Mn1 O1 C1 O2 -78.7(8) 3_755 . . . ? Mn1 O1 C1 C2 103.6(7) 3_755 . . . ? Mn1 O2 C1 O1 0.7(6) . . . . ? Mn1 O2 C1 C2 178.5(3) . . . . ? O1 C1 C2 C3 -3.0(6) . . . . ? O2 C1 C2 C3 179.0(4) . . . . ? O1 C1 C2 C7 176.1(4) . . . . ? O2 C1 C2 C7 -1.9(6) . . . . ? C7 C2 C3 C4 0.5(6) . . . . ? C1 C2 C3 C4 179.6(4) . . . . ? C9 O5 C4 C5 175.0(4) . . . . ? C9 O5 C4 C3 -4.7(7) . . . . ? C2 C3 C4 O5 178.3(4) . . . . ? C2 C3 C4 C5 -1.3(7) . . . . ? O5 C4 C5 C6 -178.6(4) . . . . ? C3 C4 C5 C6 1.0(7) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C4 C5 C6 C8 -179.4(4) . . . . ? C5 C6 C7 C2 -1.0(6) . . . . ? C8 C6 C7 C2 178.6(4) . . . . ? C3 C2 C7 C6 0.7(6) . . . . ? C1 C2 C7 C6 -178.4(4) . . . . ? Mn1 O4 C8 O3 -3.4(5) 4_456 . . . ? Mn1 O4 C8 C6 175.8(3) 4_456 . . . ? Mn1 O3 C8 O4 3.2(4) 4_456 . . . ? Mn1 O3 C8 C6 -176.0(4) 4_456 . . . ? C5 C6 C8 O4 2.7(6) . . . . ? C7 C6 C8 O4 -176.8(4) . . . . ? C5 C6 C8 O3 -178.1(4) . . . . ? C7 C6 C8 O3 2.4(6) . . . . ? C5 C6 C8 Mn1 48(4) . . . 4_456 ? C7 C6 C8 Mn1 -132(3) . . . 4_456 ? C16 N3 C10 C11 178.7(5) . . . . ? Mn1 N3 C10 C11 -3.4(8) . . . . ? C16 N3 C10 C15 -1.1(5) . . . . ? Mn1 N3 C10 C15 176.8(3) . . . . ? N3 C10 C11 C12 179.4(5) . . . . ? C15 C10 C11 C12 -0.8(7) . . . . ? C10 C11 C12 C13 -1.0(8) . . . . ? C11 C12 C13 C14 1.8(9) . . . . ? C12 C13 C14 C15 -0.6(8) . . . . ? C13 C14 C15 N4 -179.9(5) . . . . ? C13 C14 C15 C10 -1.3(7) . . . . ? C16 N4 C15 C14 178.6(5) . . . . ? C17 N4 C15 C14 -2.1(8) . . . . ? C16 N4 C15 C10 -0.2(5) . . . . ? C17 N4 C15 C10 179.1(4) . . . . ? N3 C10 C15 C14 -178.1(4) . . . . ? C11 C10 C15 C14 2.0(7) . . . . ? N3 C10 C15 N4 0.8(5) . . . . ? C11 C10 C15 N4 -179.0(4) . . . . ? C10 N3 C16 N4 1.0(6) . . . . ? Mn1 N3 C16 N4 -177.4(3) . . . . ? C15 N4 C16 N3 -0.5(6) . . . . ? C17 N4 C16 N3 -179.9(4) . . . . ? C16 N4 C17 C18 -4.3(7) . . . . ? C15 N4 C17 C18 176.5(4) . . . . ? N4 C17 C18 C19 178.2(4) . . . . ? C17 C18 C19 C20 -178.5(4) . . . . ? C27 N2 C20 C19 -3.5(7) . . . . ? C21 N2 C20 C19 175.7(4) . . . . ? C18 C19 C20 N2 177.9(4) . . . . ? C27 N2 C21 C22 -179.4(5) . . . . ? C20 N2 C21 C22 1.2(8) . . . . ? C27 N2 C21 C26 0.2(5) . . . . ? C20 N2 C21 C26 -179.2(4) . . . . ? N2 C21 C22 C23 177.8(5) . . . . ? C26 C21 C22 C23 -1.7(7) . . . . ? C21 C22 C23 C24 1.3(8) . . . . ? C22 C23 C24 C25 0.2(9) . . . . ? C23 C24 C25 C26 -1.2(8) . . . . ? C24 C25 C26 N1 -178.0(5) . . . . ? C24 C25 C26 C21 0.7(7) . . . . ? C27 N1 C26 C25 178.6(5) . . . . ? Mn1 N1 C26 C25 2.7(8) 6_556 . . . ? C27 N1 C26 C21 -0.3(5) . . . . ? Mn1 N1 C26 C21 -176.1(3) 6_556 . . . ? C22 C21 C26 C25 0.8(7) . . . . ? N2 C21 C26 C25 -178.9(4) . . . . ? C22 C21 C26 N1 179.7(4) . . . . ? N2 C21 C26 N1 0.1(5) . . . . ? C26 N1 C27 N2 0.4(5) . . . . ? Mn1 N1 C27 N2 177.0(3) 6_556 . . . ? C21 N2 C27 N1 -0.4(5) . . . . ? C20 N2 C27 N1 178.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.307 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 943594'