# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H42 Cu2 Mn N4 O8' _chemical_formula_weight 984.90 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' 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 24.025(3) _cell_length_b 9.4785(11) _cell_length_c 18.776(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4275.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28271 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 25.2 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2020 _exptl_absorpt_coefficient_mu 1.337 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9122 _exptl_absorpt_correction_T_max 0.9361 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28271 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.20 _reflns_number_total 7606 _reflns_number_gt 7006 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows (Farrugia, 1997)' _computing_publication_material 'Platon99 (Spek, 1999)' _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. twinning (hkl, -h,-k, -l ) was found with basf refining to 0.332(1) ; _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^)+(0.0306P)^2^+0.8567P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 7606 _refine_ls_number_parameters 573 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.194 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.066354(15) -0.16999(4) 0.91948(2) 0.03720(10) Uani 1 1 d . . . Cu2 Cu 0.193959(16) 0.23410(4) 0.71012(2) 0.04149(11) Uani 1 1 d . A . Mn3 Mn 0.128758(19) 0.03156(5) 0.81330(3) 0.03327(10) Uani 1 1 d . A . C2 C 0.12819(15) -0.4230(4) 0.9529(2) 0.0491(9) Uani 1 1 d . . . H2 H 0.1337 -0.5031 0.9806 0.059 Uiso 1 1 calc R . . C3 C 0.16323(14) -0.4100(4) 0.89166(19) 0.0433(8) Uani 1 1 d . . . C4 C 0.19896(16) -0.5239(4) 0.8756(2) 0.0552(10) Uani 1 1 d . . . H4 H 0.1967 -0.6059 0.9027 0.066 Uiso 1 1 calc R . . C5 C 0.23641(16) -0.5164(4) 0.8218(3) 0.0595(10) Uani 1 1 d . . . H5 H 0.2603 -0.5916 0.8131 0.071 Uiso 1 1 calc R . . C6 C 0.23892(15) -0.3980(4) 0.7802(2) 0.0561(10) Uani 1 1 d . . . H6 H 0.2645 -0.3937 0.7431 0.067 Uiso 1 1 calc R . . C7 C 0.20398(14) -0.2850(4) 0.79259(19) 0.0462(8) Uani 1 1 d . . . H7 H 0.2058 -0.2061 0.7632 0.055 Uiso 1 1 calc R . . C8 C 0.16586(13) -0.2879(3) 0.84898(18) 0.0399(7) Uani 1 1 d . . . C9 C 0.06494(17) -0.3681(5) 1.0446(2) 0.0635(12) Uani 1 1 d . . . H9A H 0.0789 -0.3002 1.0789 0.076 Uiso 1 1 calc R . . H9B H 0.0766 -0.4611 1.0601 0.076 Uiso 1 1 calc R . . C10 C 0.00282(17) -0.3625(5) 1.0446(2) 0.0630(11) Uani 1 1 d . . . H10A H -0.0106 -0.3955 1.0904 0.076 Uiso 1 1 calc R . . H10B H -0.0110 -0.4268 1.0085 0.076 Uiso 1 1 calc R . . C11 C -0.02100(17) -0.2177(4) 1.0307(2) 0.0602(10) Uani 1 1 d . . . H11A H -0.0607 -0.2191 1.0400 0.072 Uiso 1 1 calc R . . H11B H -0.0041 -0.1505 1.0630 0.072 Uiso 1 1 calc R . . C12A C 0.1970(3) 0.4201(7) 0.5830(3) 0.115(2) Uani 0.567(8) 1 d PD A 1 H12A H 0.1853 0.3475 0.5499 0.138 Uiso 0.567(8) 1 calc PR A 1 H12B H 0.1840 0.5097 0.5643 0.138 Uiso 0.567(8) 1 calc PR A 1 C13A C 0.2537(3) 0.4228(10) 0.5838(4) 0.0628(18) Uani 0.567(8) 1 d PD A 1 H13A H 0.2653 0.4953 0.6170 0.075 Uiso 0.567(8) 1 calc PR A 1 H13B H 0.2663 0.4515 0.5369 0.075 Uiso 0.567(8) 1 calc PR A 1 C14A C 0.2826(2) 0.2925(7) 0.6025(3) 0.111(2) Uani 0.567(8) 1 d PD A 1 H14A H 0.3222 0.3081 0.5969 0.133 Uiso 0.567(8) 1 calc PR A 1 H14B H 0.2718 0.2203 0.5686 0.133 Uiso 0.567(8) 1 calc PR A 1 C12B C 0.1970(3) 0.4201(7) 0.5830(3) 0.115(2) Uani 0.433(8) 1 d PD A 2 H12C H 0.1692 0.4103 0.5458 0.138 Uiso 0.433(8) 1 calc PR A 2 H12D H 0.2086 0.5181 0.5828 0.138 Uiso 0.433(8) 1 calc PR A 2 C13B C 0.2441(4) 0.3378(13) 0.5620(5) 0.0628(18) Uani 0.433(8) 1 d PD A 2 H13C H 0.2290 0.2550 0.5385 0.075 Uiso 0.433(8) 1 calc PR A 2 H13D H 0.2627 0.3921 0.5252 0.075 Uiso 0.433(8) 1 calc PR A 2 C14B C 0.2826(2) 0.2925(7) 0.6025(3) 0.111(2) Uani 0.433(8) 1 d PD A 2 H14C H 0.3092 0.3689 0.6074 0.133 Uiso 0.433(8) 1 calc PR A 2 H14D H 0.3014 0.2181 0.5764 0.133 Uiso 0.433(8) 1 calc PR A 2 C15 C 0.13083(18) 0.4806(4) 0.6700(2) 0.0614(11) Uani 1 1 d . A . H15 H 0.1259 0.5594 0.6412 0.074 Uiso 1 1 calc R . . C16 C 0.09457(15) 0.4702(4) 0.73078(19) 0.0478(9) Uani 1 1 d . . . C17 C 0.05991(17) 0.5853(4) 0.7454(3) 0.0647(11) Uani 1 1 d . . . H17 H 0.0619 0.6648 0.7165 0.078 Uiso 1 1 calc R . . C18 C 0.02313(17) 0.5842(4) 0.8012(3) 0.0685(12) Uani 1 1 d . . . H18 H 0.0008 0.6622 0.8108 0.082 Uiso 1 1 calc R . . C19 C 0.02005(15) 0.4639(4) 0.8430(2) 0.0592(10) Uani 1 1 d . . . H19 H -0.0054 0.4609 0.8803 0.071 Uiso 1 1 calc R . . C20 C 0.05349(14) 0.3494(4) 0.8308(2) 0.0476(9) Uani 1 1 d . . . H20 H 0.0509 0.2709 0.8604 0.057 Uiso 1 1 calc R . . C21 C 0.09165(13) 0.3493(3) 0.77396(18) 0.0394(8) Uani 1 1 d . A . C22 C 0.31325(15) 0.1870(4) 0.7099(2) 0.0552(9) Uani 1 1 d . A . H22 H 0.3481 0.2009 0.6894 0.066 Uiso 1 1 calc R . . C23 C 0.31310(14) 0.1118(4) 0.77612(19) 0.0462(8) Uani 1 1 d . . . C24 C 0.36450(15) 0.0632(4) 0.8027(2) 0.0615(11) Uani 1 1 d . . . H24 H 0.3973 0.0922 0.7808 0.074 Uiso 1 1 calc R . . C25 C 0.36735(17) -0.0244(5) 0.8592(2) 0.0703(12) Uani 1 1 d . . . H25 H 0.4017 -0.0558 0.8757 0.084 Uiso 1 1 calc R . . C26 C 0.31907(16) -0.0671(5) 0.8923(2) 0.0623(11) Uani 1 1 d . . . H26 H 0.3210 -0.1291 0.9306 0.075 Uiso 1 1 calc R . . C27 C 0.26843(15) -0.0196(4) 0.86980(19) 0.0484(8) Uani 1 1 d . . . H27 H 0.2367 -0.0459 0.8948 0.058 Uiso 1 1 calc R . . C28 C 0.26301(12) 0.0676(3) 0.81022(18) 0.0374(7) Uani 1 1 d . A . C30 C 0.13417(15) -0.0201(4) 0.64666(19) 0.0452(8) Uani 1 1 d . A . C31 C 0.11185(16) -0.1001(4) 0.58316(19) 0.0496(9) Uani 1 1 d . . . C32 C 0.05929(19) -0.1571(4) 0.5840(3) 0.0658(12) Uani 1 1 d . . . H32 H 0.0376 -0.1507 0.6249 0.079 Uiso 1 1 calc R . . C33 C 0.0380(2) -0.2254(5) 0.5228(3) 0.0911(16) Uani 1 1 d . . . H33 H 0.0021 -0.2621 0.5225 0.109 Uiso 1 1 calc R . . C34 C 0.0716(3) -0.2363(6) 0.4639(3) 0.0978(19) Uani 1 1 d . . . H34 H 0.0580 -0.2808 0.4233 0.117 Uiso 1 1 calc R . . C35 C 0.1239(3) -0.1840(6) 0.4632(3) 0.0976(18) Uani 1 1 d . . . H35 H 0.1465 -0.1957 0.4234 0.117 Uiso 1 1 calc R . . C36 C 0.1434(2) -0.1126(5) 0.5229(2) 0.0726(12) Uani 1 1 d . . . H36 H 0.1787 -0.0723 0.5217 0.087 Uiso 1 1 calc R . . C37 C 0.12616(14) 0.0858(3) 0.97962(18) 0.0403(8) Uani 1 1 d . A . C38 C 0.14520(16) 0.1788(3) 1.03934(18) 0.0447(8) Uani 1 1 d . . . C39 C 0.1127(2) 0.1967(5) 1.0991(2) 0.0697(12) Uani 1 1 d . . . H39 H 0.0783 0.1518 1.1014 0.084 Uiso 1 1 calc R . . C40 C 0.1294(3) 0.2778(6) 1.1547(3) 0.100(2) Uani 1 1 d . . . H40 H 0.1061 0.2918 1.1936 0.120 Uiso 1 1 calc R . . C41 C 0.1807(3) 0.3383(5) 1.1529(3) 0.106(2) Uani 1 1 d . . . H41 H 0.1928 0.3910 1.1917 0.128 Uiso 1 1 calc R . . C42 C 0.2140(3) 0.3234(5) 1.0962(3) 0.0959(19) Uani 1 1 d . . . H42 H 0.2488 0.3661 1.0956 0.115 Uiso 1 1 calc R . . C43 C 0.19631(18) 0.2433(4) 1.0376(2) 0.0608(11) Uani 1 1 d . . . H43 H 0.2191 0.2339 0.9978 0.073 Uiso 1 1 calc R . . C50 C -0.00459(12) -0.0180(3) 0.8177(2) 0.0392(7) Uani 1 1 d . . . C51 C -0.01074(14) 0.0504(4) 0.7518(2) 0.0492(9) Uani 1 1 d . . . H51 H 0.0205 0.0857 0.7286 0.059 Uiso 1 1 calc R . . C52 C -0.06226(16) 0.0657(4) 0.7210(2) 0.0617(11) Uani 1 1 d . . . H52 H -0.0653 0.1101 0.6770 0.074 Uiso 1 1 calc R . . C53 C -0.11001(16) 0.0159(5) 0.7546(2) 0.0649(11) Uani 1 1 d . . . H53 H -0.1448 0.0273 0.7336 0.078 Uiso 1 1 calc R . . C54 C -0.10501(14) -0.0487(4) 0.8179(3) 0.0592(10) Uani 1 1 d . . . H54 H -0.1370 -0.0821 0.8402 0.071 Uiso 1 1 calc R . . C55 C -0.05343(13) -0.0681(4) 0.8517(2) 0.0454(8) Uani 1 1 d . . . C56 C -0.05293(13) -0.1292(4) 0.9211(2) 0.0487(8) Uani 1 1 d . . . H56 H -0.0875 -0.1390 0.9429 0.058 Uiso 1 1 calc R . . N1 N -0.01134(11) -0.1720(3) 0.95698(16) 0.0438(7) Uani 1 1 d . . . N2 N 0.09019(12) -0.3383(3) 0.97453(15) 0.0445(7) Uani 1 1 d . . . N3 N 0.16876(15) 0.3949(4) 0.65095(16) 0.0594(8) Uani 1 1 d D . . N4 N 0.27256(14) 0.2370(3) 0.67555(17) 0.0547(8) Uani 1 1 d D . . O1 O 0.04460(9) -0.0311(2) 0.84658(12) 0.0420(5) Uani 1 1 d . . . O2 O 0.13437(9) -0.1764(2) 0.86184(13) 0.0418(5) Uani 1 1 d . . . O3 O 0.12326(9) 0.2371(2) 0.76261(13) 0.0433(5) Uani 1 1 d . . . O4 O 0.21398(9) 0.1014(2) 0.78564(11) 0.0413(5) Uani 1 1 d . . . O5 O 0.09581(11) -0.0162(3) 0.99644(13) 0.0544(6) Uani 1 1 d . . . O6 O 0.14253(10) 0.1174(2) 0.91831(13) 0.0482(5) Uani 1 1 d . . . O7 O 0.11545(10) -0.0537(2) 0.70730(13) 0.0472(5) Uani 1 1 d . . . O8 O 0.16975(12) 0.0697(3) 0.63381(14) 0.0640(7) 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 0.03521(19) 0.0354(2) 0.0410(2) 0.00659(18) 0.00398(18) -0.00311(16) Cu2 0.0471(2) 0.0419(2) 0.0355(2) 0.00441(19) 0.00787(19) -0.00654(18) Mn3 0.0338(2) 0.0325(2) 0.0335(2) 0.00308(19) 0.00345(19) -0.00349(18) C2 0.054(2) 0.039(2) 0.055(2) 0.0106(17) -0.0025(18) 0.0036(17) C3 0.0380(18) 0.0400(19) 0.052(2) 0.0051(16) -0.0037(15) -0.0014(15) C4 0.057(2) 0.038(2) 0.070(3) 0.0044(19) -0.002(2) 0.0059(17) C5 0.052(2) 0.047(2) 0.079(3) -0.012(2) -0.003(2) 0.0141(17) C6 0.047(2) 0.056(2) 0.065(3) -0.012(2) 0.0054(18) 0.0061(18) C7 0.0448(19) 0.0425(19) 0.051(2) 0.0013(16) 0.0040(15) 0.0002(15) C8 0.0340(17) 0.0347(17) 0.051(2) -0.0029(15) -0.0020(15) -0.0019(14) C9 0.069(3) 0.068(3) 0.053(3) 0.022(2) 0.0105(19) 0.006(2) C10 0.068(3) 0.065(3) 0.056(2) 0.018(2) 0.020(2) -0.004(2) C11 0.057(2) 0.072(3) 0.051(2) 0.009(2) 0.0193(19) 0.003(2) C12A 0.150(6) 0.132(5) 0.063(3) 0.049(3) 0.038(3) 0.037(4) C13A 0.065(4) 0.082(6) 0.041(4) 0.020(4) 0.002(3) -0.023(4) C14A 0.097(4) 0.164(6) 0.071(3) 0.049(4) 0.041(3) 0.000(4) C12B 0.150(6) 0.132(5) 0.063(3) 0.049(3) 0.038(3) 0.037(4) C13B 0.065(4) 0.082(6) 0.041(4) 0.020(4) 0.002(3) -0.023(4) C14B 0.097(4) 0.164(6) 0.071(3) 0.049(4) 0.041(3) 0.000(4) C15 0.075(3) 0.049(2) 0.060(3) 0.024(2) -0.005(2) -0.002(2) C16 0.050(2) 0.0385(19) 0.055(2) 0.0032(16) -0.0079(16) -0.0037(16) C17 0.063(3) 0.039(2) 0.092(3) 0.010(2) -0.011(2) 0.0024(18) C18 0.052(2) 0.044(2) 0.110(4) -0.001(2) 0.003(2) 0.0048(18) C19 0.043(2) 0.053(2) 0.082(3) -0.004(2) 0.0066(19) 0.0004(18) C20 0.0428(19) 0.0365(18) 0.064(3) 0.0007(17) 0.0063(16) -0.0016(15) C21 0.0350(17) 0.0335(17) 0.050(2) -0.0015(15) -0.0023(15) -0.0040(14) C22 0.042(2) 0.062(2) 0.062(2) -0.005(2) 0.023(2) -0.0118(17) C23 0.0437(19) 0.047(2) 0.048(2) -0.0079(16) 0.0093(15) -0.0089(16) C24 0.039(2) 0.075(3) 0.071(3) -0.006(2) 0.0025(19) -0.0079(19) C25 0.046(2) 0.090(3) 0.075(3) 0.003(3) -0.010(2) 0.001(2) C26 0.055(2) 0.080(3) 0.052(2) 0.010(2) -0.0094(19) -0.001(2) C27 0.046(2) 0.059(2) 0.0405(19) 0.0009(17) 0.0000(15) -0.0017(17) C28 0.0358(16) 0.0421(17) 0.0345(16) -0.0104(16) 0.0050(15) -0.0042(13) C30 0.049(2) 0.045(2) 0.041(2) -0.0061(17) -0.0026(16) 0.0028(17) C31 0.066(2) 0.041(2) 0.042(2) -0.0019(16) -0.0146(17) 0.0030(18) C32 0.074(3) 0.051(3) 0.073(3) -0.008(2) -0.016(2) 0.000(2) C33 0.086(4) 0.075(3) 0.112(5) -0.013(3) -0.037(4) -0.016(3) C34 0.133(5) 0.091(4) 0.069(4) -0.030(3) -0.031(4) -0.001(4) C35 0.128(5) 0.109(5) 0.056(3) -0.032(3) -0.012(3) -0.010(4) C36 0.088(3) 0.083(3) 0.046(2) -0.013(2) -0.007(2) -0.007(3) C37 0.0450(19) 0.0358(19) 0.040(2) -0.0012(15) -0.0023(15) 0.0010(15) C38 0.062(2) 0.0343(18) 0.0377(19) 0.0048(14) -0.0054(16) 0.0009(16) C39 0.093(3) 0.066(3) 0.050(2) -0.005(2) 0.010(2) -0.014(2) C40 0.174(6) 0.075(3) 0.051(3) -0.017(3) 0.005(3) -0.007(4) C41 0.202(7) 0.055(3) 0.062(4) -0.013(3) -0.043(4) -0.014(4) C42 0.128(5) 0.070(3) 0.089(4) 0.008(3) -0.052(4) -0.034(3) C43 0.069(3) 0.052(2) 0.061(3) 0.004(2) -0.016(2) -0.016(2) C50 0.0365(17) 0.0326(16) 0.0485(18) 0.0005(16) -0.0003(16) 0.0042(13) C51 0.0445(19) 0.045(2) 0.059(2) 0.0087(17) -0.0016(17) 0.0015(16) C52 0.056(2) 0.065(3) 0.064(3) 0.017(2) -0.008(2) 0.0085(18) C53 0.041(2) 0.074(3) 0.080(3) 0.012(2) -0.017(2) 0.0014(19) C54 0.0328(18) 0.066(2) 0.079(3) 0.012(2) 0.001(2) -0.0019(17) C55 0.0369(18) 0.0406(19) 0.059(2) 0.0006(17) 0.0005(16) 0.0016(14) C56 0.0355(18) 0.048(2) 0.063(2) 0.004(2) 0.013(2) -0.0032(14) N1 0.0382(15) 0.0443(17) 0.0489(17) 0.0049(13) 0.0084(13) -0.0021(13) N2 0.0448(17) 0.0438(16) 0.0449(17) 0.0117(13) 0.0013(13) -0.0023(14) N3 0.077(2) 0.061(2) 0.0397(17) 0.0156(15) 0.0105(16) 0.0002(18) N4 0.0520(19) 0.067(2) 0.0452(18) 0.0083(16) 0.0173(15) -0.0095(16) O1 0.0323(11) 0.0445(13) 0.0492(13) 0.0131(11) -0.0004(10) -0.0034(10) O2 0.0429(13) 0.0324(13) 0.0502(14) 0.0074(10) 0.0110(11) 0.0038(10) O3 0.0475(13) 0.0353(12) 0.0471(14) 0.0048(10) 0.0107(11) 0.0000(10) O4 0.0362(12) 0.0461(13) 0.0416(13) 0.0115(11) 0.0055(10) -0.0034(10) O5 0.0681(17) 0.0518(15) 0.0433(13) -0.0011(12) 0.0044(12) -0.0221(13) O6 0.0580(13) 0.0508(14) 0.0359(13) -0.0005(12) 0.0031(12) -0.0099(11) O7 0.0522(13) 0.0475(14) 0.0419(13) -0.0034(12) 0.0003(12) -0.0056(11) O8 0.0764(18) 0.0694(18) 0.0463(15) -0.0171(13) 0.0148(13) -0.0307(16) _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 O2 1.961(2) . ? Cu1 O1 1.970(2) . ? Cu1 N2 1.985(3) . ? Cu1 N1 1.995(3) . ? Cu1 O5 2.171(2) . ? Cu1 Mn3 3.1419(6) . ? Cu2 O4 1.955(2) . ? Cu2 O3 1.964(2) . ? Cu2 N3 1.981(3) . ? Cu2 N4 1.997(3) . ? Cu2 O8 2.195(3) . ? Cu2 Mn3 3.1452(6) . ? Mn3 O6 2.158(2) . ? Mn3 O7 2.172(2) . ? Mn3 O3 2.173(2) . ? Mn3 O2 2.175(2) . ? Mn3 O1 2.198(2) . ? Mn3 O4 2.214(2) . ? C2 N2 1.281(4) . ? C2 C3 1.431(5) . ? C3 C8 1.409(5) . ? C3 C4 1.411(5) . ? C4 C5 1.356(6) . ? C5 C6 1.368(6) . ? C6 C7 1.381(5) . ? C7 C8 1.400(5) . ? C8 O2 1.322(4) . ? C9 N2 1.477(4) . ? C9 C10 1.493(5) . ? C10 C11 1.509(6) . ? C11 N1 1.468(5) . ? C12A C13A 1.363(9) . ? C12A N3 1.464(5) . ? C13A C14A 1.460(10) . ? C14A N4 1.489(6) . ? C12B C13B 1.431(11) . ? C12B N3 1.464(5) . ? C13B C14B 1.271(10) . ? C14B N4 1.489(6) . ? C15 N3 1.272(5) . ? C15 C16 1.439(5) . ? C16 C17 1.400(5) . ? C16 C21 1.405(5) . ? C17 C18 1.370(6) . ? C18 C19 1.387(6) . ? C19 C20 1.370(5) . ? C20 C21 1.407(5) . ? C21 O3 1.324(4) . ? C22 N4 1.263(5) . ? C22 C23 1.433(6) . ? C23 C24 1.410(5) . ? C23 C28 1.426(4) . ? C24 C25 1.348(6) . ? C25 C26 1.377(6) . ? C26 C27 1.365(5) . ? C27 C28 1.396(5) . ? C28 O4 1.305(4) . ? C30 O8 1.230(4) . ? C30 O7 1.265(4) . ? C30 C31 1.512(5) . ? C31 C36 1.368(6) . ? C31 C32 1.374(6) . ? C32 C33 1.414(7) . ? C33 C34 1.375(8) . ? C34 C35 1.350(8) . ? C35 C36 1.391(6) . ? C37 O5 1.251(4) . ? C37 O6 1.253(4) . ? C37 C38 1.498(5) . ? C38 C43 1.372(5) . ? C38 C39 1.377(5) . ? C39 C40 1.358(7) . ? C40 C41 1.359(9) . ? C41 C42 1.340(9) . ? C42 C43 1.402(7) . ? C50 O1 1.306(4) . ? C50 C51 1.405(5) . ? C50 C55 1.418(5) . ? C51 C52 1.374(5) . ? C52 C53 1.392(6) . ? C53 C54 1.342(6) . ? C54 C55 1.404(5) . ? C55 C56 1.425(5) . ? C56 N1 1.272(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O1 81.85(9) . . ? O2 Cu1 N2 91.27(10) . . ? O1 Cu1 N2 167.27(11) . . ? O2 Cu1 N1 166.95(11) . . ? O1 Cu1 N1 90.20(10) . . ? N2 Cu1 N1 94.50(11) . . ? O2 Cu1 O5 96.68(10) . . ? O1 Cu1 O5 95.74(10) . . ? N2 Cu1 O5 95.69(11) . . ? N1 Cu1 O5 94.39(11) . . ? O2 Cu1 Mn3 43.19(6) . . ? O1 Cu1 Mn3 43.89(6) . . ? N2 Cu1 Mn3 132.94(8) . . ? N1 Cu1 Mn3 132.55(8) . . ? O5 Cu1 Mn3 81.86(7) . . ? O4 Cu2 O3 81.86(9) . . ? O4 Cu2 N3 167.63(12) . . ? O3 Cu2 N3 90.34(12) . . ? O4 Cu2 N4 90.68(11) . . ? O3 Cu2 N4 168.73(13) . . ? N3 Cu2 N4 95.52(14) . . ? O4 Cu2 O8 94.70(11) . . ? O3 Cu2 O8 96.24(10) . . ? N3 Cu2 O8 95.68(13) . . ? N4 Cu2 O8 92.76(12) . . ? O4 Cu2 Mn3 44.22(6) . . ? O3 Cu2 Mn3 43.04(6) . . ? N3 Cu2 Mn3 131.52(10) . . ? N4 Cu2 Mn3 132.80(10) . . ? O8 Cu2 Mn3 80.61(7) . . ? O6 Mn3 O7 179.51(10) . . ? O6 Mn3 O3 94.09(9) . . ? O7 Mn3 O3 85.59(9) . . ? O6 Mn3 O2 87.10(9) . . ? O7 Mn3 O2 93.21(9) . . ? O3 Mn3 O2 178.78(10) . . ? O6 Mn3 O1 89.04(9) . . ? O7 Mn3 O1 91.41(9) . . ? O3 Mn3 O1 108.11(8) . . ? O2 Mn3 O1 72.14(8) . . ? O6 Mn3 O4 87.69(8) . . ? O7 Mn3 O4 91.86(8) . . ? O3 Mn3 O4 71.65(8) . . ? O2 Mn3 O4 108.17(8) . . ? O1 Mn3 O4 176.69(9) . . ? O6 Mn3 Cu1 73.91(6) . . ? O7 Mn3 Cu1 106.56(6) . . ? O3 Mn3 Cu1 142.59(6) . . ? O2 Mn3 Cu1 38.09(6) . . ? O1 Mn3 Cu1 38.41(6) . . ? O4 Mn3 Cu1 140.54(6) . . ? O6 Mn3 Cu2 104.84(6) . . ? O7 Mn3 Cu2 74.68(6) . . ? O3 Mn3 Cu2 38.09(6) . . ? O2 Mn3 Cu2 141.27(6) . . ? O1 Mn3 Cu2 142.95(6) . . ? O4 Mn3 Cu2 38.03(6) . . ? Cu1 Mn3 Cu2 178.40(2) . . ? N2 C2 C3 128.3(3) . . ? C8 C3 C4 118.6(3) . . ? C8 C3 C2 123.7(3) . . ? C4 C3 C2 117.6(3) . . ? C5 C4 C3 121.5(4) . . ? C4 C5 C6 119.8(4) . . ? C5 C6 C7 120.9(4) . . ? C6 C7 C8 120.6(3) . . ? O2 C8 C7 119.8(3) . . ? O2 C8 C3 121.8(3) . . ? C7 C8 C3 118.4(3) . . ? N2 C9 C10 113.8(3) . . ? C9 C10 C11 114.3(3) . . ? N1 C11 C10 111.8(3) . . ? C13A C12A N3 117.2(6) . . ? C12A C13A C14A 117.6(7) . . ? C13A C14A N4 116.3(5) . . ? C13B C12B N3 121.2(6) . . ? C14B C13B C12B 126.5(9) . . ? C13B C14B N4 123.5(6) . . ? N3 C15 C16 127.8(3) . . ? C17 C16 C21 119.5(4) . . ? C17 C16 C15 117.6(3) . . ? C21 C16 C15 122.9(3) . . ? C18 C17 C16 121.9(4) . . ? C17 C18 C19 118.3(4) . . ? C20 C19 C18 121.7(4) . . ? C19 C20 C21 120.6(4) . . ? O3 C21 C16 122.2(3) . . ? O3 C21 C20 119.7(3) . . ? C16 C21 C20 118.0(3) . . ? N4 C22 C23 128.9(3) . . ? C24 C23 C28 118.9(3) . . ? C24 C23 C22 117.9(3) . . ? C28 C23 C22 122.5(3) . . ? C25 C24 C23 121.6(4) . . ? C24 C25 C26 119.6(4) . . ? C27 C26 C25 120.9(4) . . ? C26 C27 C28 121.8(4) . . ? O4 C28 C27 120.8(3) . . ? O4 C28 C23 122.0(3) . . ? C27 C28 C23 117.1(3) . . ? O8 C30 O7 126.7(3) . . ? O8 C30 C31 116.0(3) . . ? O7 C30 C31 117.2(3) . . ? C36 C31 C32 119.0(4) . . ? C36 C31 C30 120.0(4) . . ? C32 C31 C30 121.0(4) . . ? C31 C32 C33 120.2(5) . . ? C34 C33 C32 118.4(5) . . ? C35 C34 C33 121.8(5) . . ? C34 C35 C36 119.0(5) . . ? C31 C36 C35 121.4(5) . . ? O5 C37 O6 126.8(3) . . ? O5 C37 C38 116.3(3) . . ? O6 C37 C38 116.8(3) . . ? C43 C38 C39 118.2(4) . . ? C43 C38 C37 121.2(3) . . ? C39 C38 C37 120.6(3) . . ? C40 C39 C38 121.9(5) . . ? C41 C40 C39 119.2(6) . . ? C42 C41 C40 121.1(5) . . ? C41 C42 C43 120.0(6) . . ? C38 C43 C42 119.6(5) . . ? O1 C50 C51 120.3(3) . . ? O1 C50 C55 122.0(3) . . ? C51 C50 C55 117.7(3) . . ? C52 C51 C50 120.9(3) . . ? C51 C52 C53 121.1(4) . . ? C54 C53 C52 118.9(4) . . ? C53 C54 C55 122.6(4) . . ? C54 C55 C50 118.9(3) . . ? C54 C55 C56 118.3(3) . . ? C50 C55 C56 122.7(3) . . ? N1 C56 C55 128.4(3) . . ? C56 N1 C11 118.0(3) . . ? C56 N1 Cu1 123.0(2) . . ? C11 N1 Cu1 118.9(2) . . ? C2 N2 C9 117.1(3) . . ? C2 N2 Cu1 123.0(2) . . ? C9 N2 Cu1 120.0(2) . . ? C15 N3 C12B 118.2(4) . . ? C15 N3 C12A 118.2(4) . . ? C12B N3 C12A 0.0(2) . . ? C15 N3 Cu2 123.5(3) . . ? C12B N3 Cu2 118.2(3) . . ? C12A N3 Cu2 118.2(3) . . ? C22 N4 C14B 118.5(4) . . ? C22 N4 C14A 118.5(4) . . ? C14B N4 C14A 0.00(17) . . ? C22 N4 Cu2 124.1(3) . . ? C14B N4 Cu2 117.2(3) . . ? C14A N4 Cu2 117.2(3) . . ? C50 O1 Cu1 126.3(2) . . ? C50 O1 Mn3 133.5(2) . . ? Cu1 O1 Mn3 97.70(9) . . ? C8 O2 Cu1 127.0(2) . . ? C8 O2 Mn3 133.1(2) . . ? Cu1 O2 Mn3 98.72(9) . . ? C21 O3 Cu2 126.1(2) . . ? C21 O3 Mn3 133.2(2) . . ? Cu2 O3 Mn3 98.87(9) . . ? C28 O4 Cu2 129.5(2) . . ? C28 O4 Mn3 132.7(2) . . ? Cu2 O4 Mn3 97.76(9) . . ? C37 O5 Cu1 122.7(2) . . ? C37 O6 Mn3 134.5(2) . . ? C30 O7 Mn3 132.8(2) . . ? C30 O8 Cu2 123.2(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.288 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 951180' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 Mn N10 O4' _chemical_formula_weight 826.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.453(5) _cell_length_b 11.210(5) _cell_length_c 15.890(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 101.832(5) _cell_angle_gamma 90.000(5) _cell_volume 1648.1(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28808 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 36.8 _exptl_crystal_description rectangular _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 842 _exptl_absorpt_coefficient_mu 1.713 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.8895 _exptl_absorpt_correction_T_max 0.9504 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28808 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 36.82 _reflns_number_total 8171 _reflns_number_gt 5264 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows (Farrugia, 1997)' _computing_publication_material 'Platon99 (Spek, 1999)' _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^)+(0.0507P)^2^+0.0032P] 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 8171 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Cu1 Cu 0.249256(19) 0.161561(15) 0.561354(12) 0.03441(7) Uani 1 1 d . . . Mn3 Mn 0.0000 0.0000 0.5000 0.03053(8) Uani 1 2 d S . . O1 O 0.15528(11) 0.04160(9) 0.61963(7) 0.0342(2) Uani 1 1 d . . . O2 O 0.20576(11) 0.04728(10) 0.46840(7) 0.0415(3) Uani 1 1 d . . . N4 N 0.24069(14) 0.28017(11) 0.64937(9) 0.0371(3) Uani 1 1 d . . . N5 N 0.39613(14) 0.23982(12) 0.50821(9) 0.0384(3) Uani 1 1 d . . . N2 N 0.12641(16) -0.25295(13) 0.53804(11) 0.0477(3) Uani 1 1 d . . . N1 N 0.02814(17) -0.19425(14) 0.50675(12) 0.0520(4) Uani 1 1 d . . . C17 C 0.50325(17) 0.02996(17) 0.35565(11) 0.0416(3) Uani 1 1 d . . . C12 C 0.41641(15) 0.07360(13) 0.41053(9) 0.0338(3) Uani 1 1 d . . . C5 C 0.15986(17) 0.14702(15) 0.75133(11) 0.0387(3) Uani 1 1 d . . . C6 C 0.14284(14) 0.04215(14) 0.70096(10) 0.0334(3) Uani 1 1 d . . . C13 C 0.28924(15) 0.01119(13) 0.41691(9) 0.0314(3) Uani 1 1 d . . . C7 C 0.20212(17) 0.25997(15) 0.72094(11) 0.0399(3) Uani 1 1 d . . . C15 C 0.3392(2) -0.12953(17) 0.31108(12) 0.0462(4) Uani 1 1 d . . . C9 C 0.4352(2) 0.40508(16) 0.61832(14) 0.0511(4) Uani 1 1 d . . . C14 C 0.25181(18) -0.09005(15) 0.36527(11) 0.0400(3) Uani 1 1 d . . . C16 C 0.4671(2) -0.07006(18) 0.30733(12) 0.0475(4) Uani 1 1 d . . . C4 C 0.1360(2) 0.1426(2) 0.83612(12) 0.0549(5) Uani 1 1 d . . . C1 C 0.11161(19) -0.06471(17) 0.73911(12) 0.0453(4) Uani 1 1 d . . . C3 C 0.1034(2) 0.0371(3) 0.87177(14) 0.0668(6) Uani 1 1 d . . . C10 C 0.4492(3) 0.36223(18) 0.53008(14) 0.0545(5) Uani 1 1 d . . . C11 C 0.45764(17) 0.18530(15) 0.45426(11) 0.0387(3) Uani 1 1 d . . . C8 C 0.2816(2) 0.40247(15) 0.63233(15) 0.0491(4) Uani 1 1 d . . . C2 C 0.0940(2) -0.0664(2) 0.82382(13) 0.0586(5) Uani 1 1 d . . . N3 N 0.2228(2) -0.3123(2) 0.5696(2) 0.0982(9) Uani 1 1 d . . . H1 H 0.213(3) 0.431(2) 0.5847(17) 0.075(7) Uiso 1 1 d . . . H3 H 0.500(2) 0.3571(19) 0.6638(15) 0.046(5) Uiso 1 1 d . . . H2 H 0.272(2) 0.451(2) 0.6768(15) 0.055(6) Uiso 1 1 d . . . H5 H 0.547(2) 0.3580(18) 0.5246(14) 0.047(5) Uiso 1 1 d . . . H4 H 0.470(2) 0.4886(19) 0.6244(15) 0.052(6) Uiso 1 1 d . . . H6 H 0.393(3) 0.413(2) 0.4828(15) 0.062(7) Uiso 1 1 d . . . H7 H 0.202(2) 0.3264(17) 0.7593(13) 0.038(5) Uiso 1 1 d . . . H8 H 0.538(2) 0.2254(18) 0.4350(12) 0.045(5) Uiso 1 1 d . . . H9 H 0.097(2) -0.132(2) 0.7043(14) 0.051(6) Uiso 1 1 d . . . H15 H 0.314(2) -0.202(2) 0.2762(14) 0.054(6) Uiso 1 1 d . . . H16 H 0.164(2) -0.1245(19) 0.3638(13) 0.047(5) Uiso 1 1 d . . . H14 H 0.532(3) -0.099(2) 0.2709(15) 0.064(6) Uiso 1 1 d . . . H10 H 0.069(3) -0.142(3) 0.8527(19) 0.086(8) Uiso 1 1 d . . . H13 H 0.585(2) 0.0709(18) 0.3539(12) 0.047(5) Uiso 1 1 d . . . H12 H 0.137(3) 0.212(2) 0.8655(15) 0.059(6) Uiso 1 1 d . . . H11 H 0.096(3) 0.042(2) 0.9336(19) 0.078(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.04114(11) 0.03014(10) 0.03368(11) -0.00603(6) 0.01171(8) -0.01101(6) Mn3 0.02716(13) 0.03098(15) 0.03353(16) -0.00309(11) 0.00640(12) -0.00579(10) O1 0.0391(5) 0.0341(5) 0.0303(5) -0.0038(4) 0.0088(4) -0.0082(4) O2 0.0386(5) 0.0473(6) 0.0432(6) -0.0176(5) 0.0190(5) -0.0166(5) N4 0.0386(6) 0.0303(6) 0.0410(7) -0.0065(5) 0.0046(5) -0.0037(5) N5 0.0426(6) 0.0345(6) 0.0379(7) 0.0000(5) 0.0079(6) -0.0129(5) N2 0.0470(7) 0.0382(7) 0.0616(9) 0.0092(6) 0.0196(7) -0.0007(6) N1 0.0475(8) 0.0349(7) 0.0689(11) 0.0028(7) 0.0006(7) -0.0014(6) C17 0.0336(7) 0.0533(9) 0.0392(8) 0.0102(7) 0.0105(6) 0.0058(6) C12 0.0311(6) 0.0400(7) 0.0302(7) 0.0068(6) 0.0061(5) 0.0006(5) C5 0.0339(7) 0.0501(9) 0.0317(7) -0.0058(6) 0.0056(6) -0.0011(6) C6 0.0274(6) 0.0414(7) 0.0311(7) 0.0000(6) 0.0052(5) -0.0009(5) C13 0.0309(6) 0.0355(7) 0.0275(6) 0.0000(5) 0.0055(5) -0.0004(5) C7 0.0375(7) 0.0423(8) 0.0380(8) -0.0135(7) 0.0032(6) 0.0001(6) C15 0.0530(9) 0.0475(9) 0.0379(9) -0.0071(7) 0.0087(7) 0.0084(8) C9 0.0616(10) 0.0363(8) 0.0536(11) -0.0081(8) 0.0080(9) -0.0198(8) C14 0.0387(7) 0.0430(8) 0.0378(8) -0.0074(6) 0.0064(7) -0.0024(6) C16 0.0481(9) 0.0577(10) 0.0406(9) 0.0046(8) 0.0182(8) 0.0153(8) C4 0.0556(10) 0.0769(13) 0.0330(9) -0.0132(9) 0.0112(8) -0.0117(9) C1 0.0457(8) 0.0492(9) 0.0414(9) 0.0053(7) 0.0099(7) -0.0071(7) C3 0.0635(13) 0.1053(18) 0.0326(9) 0.0021(11) 0.0122(9) -0.0195(12) C10 0.0666(12) 0.0408(9) 0.0573(12) -0.0040(8) 0.0159(10) -0.0254(9) C11 0.0341(7) 0.0439(8) 0.0383(8) 0.0069(6) 0.0075(6) -0.0078(6) C8 0.0581(10) 0.0278(7) 0.0584(11) -0.0059(7) 0.0051(9) -0.0024(7) C2 0.0552(10) 0.0774(14) 0.0422(10) 0.0180(10) 0.0078(8) -0.0147(9) N3 0.0560(11) 0.0787(14) 0.161(3) 0.0564(16) 0.0241(14) 0.0148(10) _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 O2 1.9346(12) . ? Cu1 N4 1.9435(14) . ? Cu1 O1 1.9474(11) . ? Cu1 N5 1.9725(14) . ? Cu1 Mn3 2.9733(11) . ? Mn3 O2 2.1718(14) . ? Mn3 O2 2.1718(14) 3_556 ? Mn3 N1 2.1937(18) 3_556 ? Mn3 N1 2.1937(18) . ? Mn3 O1 2.2004(12) 3_556 ? Mn3 O1 2.2004(12) . ? Mn3 Cu1 2.9733(11) 3_556 ? O1 C6 1.3215(18) . ? O2 C13 1.3117(18) . ? N4 C7 1.284(2) . ? N4 C8 1.465(2) . ? N5 C11 1.285(2) . ? N5 C10 1.478(2) . ? N2 N3 1.157(3) . ? N2 N1 1.163(2) . ? C17 C16 1.362(3) . ? C17 C12 1.403(2) . ? C12 C13 1.412(2) . ? C12 C11 1.446(2) . ? C5 C4 1.412(3) . ? C5 C6 1.413(2) . ? C5 C7 1.440(3) . ? C6 C1 1.401(2) . ? C13 C14 1.403(2) . ? C15 C14 1.383(2) . ? C15 C16 1.392(3) . ? C9 C8 1.513(3) . ? C9 C10 1.514(3) . ? C4 C3 1.373(4) . ? C1 C2 1.390(3) . ? C3 C2 1.381(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 N4 165.64(5) . . ? O2 Cu1 O1 81.93(5) . . ? N4 Cu1 O1 92.28(6) . . ? O2 Cu1 N5 91.47(5) . . ? N4 Cu1 N5 98.09(6) . . ? O1 Cu1 N5 160.12(5) . . ? O2 Cu1 Mn3 46.86(3) . . ? N4 Cu1 Mn3 120.37(4) . . ? O1 Cu1 Mn3 47.72(4) . . ? N5 Cu1 Mn3 135.28(4) . . ? O2 Mn3 O2 180.0 . 3_556 ? O2 Mn3 N1 81.48(6) . 3_556 ? O2 Mn3 N1 98.52(6) 3_556 3_556 ? O2 Mn3 N1 98.52(6) . . ? O2 Mn3 N1 81.48(6) 3_556 . ? N1 Mn3 N1 180.0 3_556 . ? O2 Mn3 O1 108.81(5) . 3_556 ? O2 Mn3 O1 71.19(5) 3_556 3_556 ? N1 Mn3 O1 96.63(5) 3_556 3_556 ? N1 Mn3 O1 83.37(5) . 3_556 ? O2 Mn3 O1 71.19(5) . . ? O2 Mn3 O1 108.81(5) 3_556 . ? N1 Mn3 O1 83.37(5) 3_556 . ? N1 Mn3 O1 96.63(5) . . ? O1 Mn3 O1 180.0 3_556 . ? O2 Mn3 Cu1 40.54(3) . . ? O2 Mn3 Cu1 139.46(3) 3_556 . ? N1 Mn3 Cu1 59.43(5) 3_556 . ? N1 Mn3 Cu1 120.57(5) . . ? O1 Mn3 Cu1 139.10(3) 3_556 . ? O1 Mn3 Cu1 40.90(3) . . ? O2 Mn3 Cu1 139.46(3) . 3_556 ? O2 Mn3 Cu1 40.54(3) 3_556 3_556 ? N1 Mn3 Cu1 120.57(5) 3_556 3_556 ? N1 Mn3 Cu1 59.43(5) . 3_556 ? O1 Mn3 Cu1 40.90(3) 3_556 3_556 ? O1 Mn3 Cu1 139.10(3) . 3_556 ? Cu1 Mn3 Cu1 180.0 . 3_556 ? C6 O1 Cu1 127.05(9) . . ? C6 O1 Mn3 131.95(9) . . ? Cu1 O1 Mn3 91.38(5) . . ? C13 O2 Cu1 128.28(9) . . ? C13 O2 Mn3 138.66(9) . . ? Cu1 O2 Mn3 92.60(5) . . ? C7 N4 C8 117.57(15) . . ? C7 N4 Cu1 125.32(11) . . ? C8 N4 Cu1 117.11(12) . . ? C11 N5 C10 114.84(14) . . ? C11 N5 Cu1 121.91(11) . . ? C10 N5 Cu1 123.18(12) . . ? N3 N2 N1 179.1(2) . . ? N2 N1 Mn3 131.33(13) . . ? C16 C17 C12 121.74(16) . . ? C17 C12 C13 119.15(15) . . ? C17 C12 C11 117.79(14) . . ? C13 C12 C11 122.95(14) . . ? C4 C5 C6 119.32(17) . . ? C4 C5 C7 117.39(17) . . ? C6 C5 C7 123.28(15) . . ? O1 C6 C1 119.21(15) . . ? O1 C6 C5 122.36(14) . . ? C1 C6 C5 118.43(15) . . ? O2 C13 C14 120.17(13) . . ? O2 C13 C12 121.45(13) . . ? C14 C13 C12 118.36(13) . . ? N4 C7 C5 126.93(14) . . ? C14 C15 C16 120.55(17) . . ? C8 C9 C10 113.53(17) . . ? C15 C14 C13 120.80(16) . . ? C17 C16 C15 119.33(16) . . ? C3 C4 C5 121.1(2) . . ? C2 C1 C6 120.55(19) . . ? C4 C3 C2 119.37(19) . . ? N5 C10 C9 114.98(15) . . ? N5 C11 C12 128.18(14) . . ? N4 C8 C9 110.06(15) . . ? C3 C2 C1 121.06(19) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 36.82 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.501 _refine_diff_density_min -0.951 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 951181' ####################################################################### # # 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_3_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 Cu2 Mn N6 O6' _chemical_formula_weight 826.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 '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 10.0774(17) _cell_length_b 11.887(2) _cell_length_c 13.945(2) _cell_angle_alpha 92.246(2) _cell_angle_beta 100.840(2) _cell_angle_gamma 91.095(2) _cell_volume 1638.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 11421 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 842 _exptl_absorpt_coefficient_mu 1.722 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.8890 _exptl_absorpt_correction_T_max 0.9502 _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 11421 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5648 _reflns_number_gt 4299 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows (Farrugia, 1997)' _computing_publication_material 'Platon99 (Spek, 1999)' _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^)+(0.0484P)^2^+1.0118P] 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 5648 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.003 _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 C47 C 0.1842(4) 0.3510(3) 0.2032(3) 0.0400(10) Uani 1 1 d . . . C46 C 0.3238(4) 0.3338(4) 0.2271(3) 0.0469(11) Uani 1 1 d . . . C45 C 0.3856(4) 0.2777(4) 0.3120(4) 0.0557(13) Uani 1 1 d . . . H45 H 0.4755 0.2592 0.3154 0.067 Uiso 1 1 calc R . . C50 C 0.1333(5) 0.4032(4) 0.1169(3) 0.0500(11) Uani 1 1 d . . . H50 H 0.0410 0.4144 0.0995 0.060 Uiso 1 1 calc R . . C51 C 0.2193(6) 0.4386(4) 0.0568(4) 0.0656(14) Uani 1 1 d . . . H51 H 0.1841 0.4739 -0.0005 0.079 Uiso 1 1 calc R . . C53 C 0.4077(5) 0.3699(4) 0.1633(4) 0.0649(14) Uani 1 1 d . . . H53 H 0.5000 0.3575 0.1782 0.078 Uiso 1 1 calc R . . C52 C 0.3557(6) 0.4222(5) 0.0806(4) 0.0727(16) Uani 1 1 d . . . H52 H 0.4124 0.4471 0.0399 0.087 Uiso 1 1 calc R . . Cu1 Cu 0.05497(5) 0.13375(4) 0.07113(3) 0.03773(15) Uani 1 1 d . . . Cu2 Cu 0.14518(5) 0.28262(4) 0.39454(3) 0.04088(15) Uani 1 1 d . . . Mn1 Mn -0.11936(6) 0.25334(5) 0.21946(4) 0.03598(17) Uani 1 1 d . . . C31 C -0.0455(4) 0.3673(3) 0.5436(3) 0.0429(10) Uani 1 1 d . . . O4 O -0.1159(2) 0.2050(2) 0.06399(18) 0.0392(6) Uani 1 1 d . . . O2 O 0.0993(3) 0.3169(2) 0.25951(19) 0.0426(7) Uani 1 1 d . . . N4 N 0.0656(3) 0.1725(3) -0.0641(2) 0.0459(9) Uani 1 1 d . . . N1 N 0.1701(4) 0.2799(3) 0.5372(3) 0.0529(9) Uani 1 1 d . . . C1 C 0.0747(4) 0.0325(3) 0.2630(3) 0.0385(9) Uani 1 1 d . . . N3 N 0.2340(3) 0.0691(3) 0.1048(3) 0.0505(9) Uani 1 1 d . . . C14 C -0.2018(4) 0.2355(3) -0.0140(3) 0.0370(9) Uani 1 1 d . . . N2 N 0.3316(3) 0.2496(3) 0.3846(3) 0.0506(9) Uani 1 1 d . . . N6 N -0.2886(4) 0.1585(3) 0.2422(3) 0.0564(10) Uani 1 1 d . . . C30 C -0.1112(4) 0.3420(3) 0.4455(3) 0.0381(9) Uani 1 1 d . . . C2 C 0.0142(5) 0.0023(4) 0.3406(3) 0.0512(11) Uani 1 1 d . . . H2 H -0.0715 0.0277 0.3442 0.061 Uiso 1 1 calc R . . C7 C 0.2751(4) 0.0170(4) 0.1826(4) 0.0542(12) Uani 1 1 d . . . H7 H 0.3621 -0.0104 0.1897 0.065 Uiso 1 1 calc R . . C9 C -0.1622(4) 0.2485(3) -0.1042(3) 0.0414(10) Uani 1 1 d . . . N5 N -0.1958(4) 0.4125(3) 0.1866(3) 0.0568(10) Uani 1 1 d . . . C6 C 0.2047(4) -0.0051(3) 0.2610(3) 0.0414(10) Uani 1 1 d . . . C35 C -0.2437(4) 0.3745(3) 0.4172(3) 0.0451(10) Uani 1 1 d . . . H35 H -0.2882 0.3589 0.3532 0.054 Uiso 1 1 calc R . . C17 C 0.3349(5) 0.0810(5) 0.0410(4) 0.0741(16) Uani 1 1 d . . . H17A H 0.3811 0.1537 0.0559 0.089 Uiso 1 1 calc R . . H17B H 0.4017 0.0235 0.0561 0.089 Uiso 1 1 calc R . . C4 C 0.2093(5) -0.0999(4) 0.4118(4) 0.0604(13) Uani 1 1 d . . . H4 H 0.2541 -0.1433 0.4613 0.072 Uiso 1 1 calc R . . C36 C 0.0855(5) 0.3274(4) 0.5830(3) 0.0526(12) Uani 1 1 d . . . H36 H 0.1130 0.3371 0.6504 0.063 Uiso 1 1 calc R . . C8 C -0.0301(5) 0.2196(4) -0.1202(3) 0.0480(11) Uani 1 1 d . . . H8 H -0.0115 0.2379 -0.1807 0.058 Uiso 1 1 calc R . . C34 C -0.3106(5) 0.4292(4) 0.4815(3) 0.0530(12) Uani 1 1 d . . . H34 H -0.4000 0.4489 0.4607 0.064 Uiso 1 1 calc R . . C32 C -0.1178(5) 0.4246(4) 0.6070(3) 0.0561(12) Uani 1 1 d . . . H32 H -0.0753 0.4415 0.6712 0.067 Uiso 1 1 calc R . . C40 C -0.3448(5) 0.0866(4) 0.2702(4) 0.0544(12) Uani 1 1 d . . . C41 C -0.2307(5) 0.5028(4) 0.1901(3) 0.0512(11) Uani 1 1 d . . . C38 C 0.4194(5) 0.1906(5) 0.4641(4) 0.0741(16) Uani 1 1 d . . . H38A H 0.5118 0.1922 0.4535 0.089 Uiso 1 1 calc R . . H38B H 0.3892 0.1125 0.4632 0.089 Uiso 1 1 calc R . . C33 C -0.2469(5) 0.4556(4) 0.5773(3) 0.0591(13) Uani 1 1 d . . . H33 H -0.2923 0.4941 0.6202 0.071 Uiso 1 1 calc R . . C5 C 0.2701(5) -0.0695(4) 0.3370(4) 0.0577(12) Uani 1 1 d . . . H5 H 0.3578 -0.0921 0.3364 0.069 Uiso 1 1 calc R . . C13 C -0.3362(4) 0.2573(4) -0.0081(3) 0.0491(11) Uani 1 1 d . . . H13 H -0.3649 0.2484 0.0508 0.059 Uiso 1 1 calc R . . C3 C 0.0802(5) -0.0649(4) 0.4126(3) 0.0554(12) Uani 1 1 d . . . H3 H 0.0364 -0.0867 0.4622 0.067 Uiso 1 1 calc R . . O5 O -0.2691(5) 0.5967(3) 0.1931(3) 0.1186(18) Uani 1 1 d . . . C12 C -0.4268(5) 0.2915(4) -0.0875(3) 0.0569(12) Uani 1 1 d . . . H12 H -0.5162 0.3030 -0.0822 0.068 Uiso 1 1 calc R . . C10 C -0.2552(5) 0.2870(4) -0.1825(3) 0.0584(13) Uani 1 1 d . . . H10 H -0.2276 0.2979 -0.2415 0.070 Uiso 1 1 calc R . . C37 C 0.4140(6) 0.2469(6) 0.5625(4) 0.095(2) Uani 1 1 d . . . H37A H 0.4873 0.2192 0.6104 0.114 Uiso 1 1 calc R . . H37B H 0.4300 0.3272 0.5586 0.114 Uiso 1 1 calc R . . O6 O -0.4039(5) 0.0121(4) 0.2982(4) 0.1262(19) Uani 1 1 d . . . C11 C -0.3858(5) 0.3090(4) -0.1750(3) 0.0616(13) Uani 1 1 d . . . H11 H -0.4458 0.3353 -0.2279 0.074 Uiso 1 1 calc R . . C15 C 0.1889(5) 0.1550(5) -0.1054(4) 0.0700(15) Uani 1 1 d . . . H15A H 0.1616 0.1336 -0.1742 0.084 Uiso 1 1 calc R . . H15B H 0.2385 0.2264 -0.1008 0.084 Uiso 1 1 calc R . . C16 C 0.2795(6) 0.0719(6) -0.0604(4) 0.0893(19) Uani 1 1 d . . . H16A H 0.2321 -0.0006 -0.0731 0.107 Uiso 1 1 calc R . . H16B H 0.3547 0.0693 -0.0947 0.107 Uiso 1 1 calc R . . C39 C 0.2891(6) 0.2303(5) 0.5976(4) 0.0833(18) Uani 1 1 d . . . H39A H 0.3003 0.2628 0.6636 0.100 Uiso 1 1 calc R . . H39B H 0.2718 0.1501 0.6006 0.100 Uiso 1 1 calc R . . O3 O 0.0084(3) 0.0956(2) 0.19473(19) 0.0427(7) Uani 1 1 d . . . O1 O -0.0480(2) 0.2885(2) 0.38225(18) 0.0414(7) 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 C47 0.039(2) 0.040(2) 0.041(2) -0.0139(18) 0.0134(19) -0.0070(18) C46 0.041(2) 0.046(2) 0.056(3) -0.018(2) 0.017(2) -0.004(2) C45 0.034(2) 0.056(3) 0.076(3) -0.028(3) 0.012(2) 0.000(2) C50 0.056(3) 0.053(3) 0.044(3) 0.000(2) 0.018(2) -0.003(2) C51 0.092(4) 0.059(3) 0.053(3) -0.004(2) 0.034(3) -0.010(3) C53 0.053(3) 0.067(3) 0.080(4) -0.027(3) 0.035(3) -0.015(3) C52 0.081(4) 0.071(4) 0.079(4) -0.022(3) 0.052(3) -0.024(3) Cu1 0.0358(3) 0.0399(3) 0.0394(3) -0.0013(2) 0.0122(2) 0.0049(2) Cu2 0.0352(3) 0.0483(3) 0.0374(3) 0.0007(2) 0.0023(2) 0.0026(2) Mn1 0.0340(3) 0.0421(4) 0.0324(3) -0.0004(3) 0.0077(3) 0.0047(3) C31 0.056(3) 0.043(2) 0.032(2) 0.0051(18) 0.013(2) -0.005(2) O4 0.0334(15) 0.0526(17) 0.0319(14) 0.0037(12) 0.0059(12) 0.0120(13) O2 0.0338(15) 0.0576(18) 0.0378(15) 0.0026(13) 0.0104(12) -0.0023(13) N4 0.042(2) 0.055(2) 0.044(2) -0.0021(17) 0.0170(17) 0.0021(17) N1 0.049(2) 0.064(2) 0.041(2) 0.0059(18) -0.0052(17) 0.0029(19) C1 0.041(2) 0.034(2) 0.038(2) -0.0007(18) 0.0021(18) 0.0027(18) N3 0.042(2) 0.058(2) 0.057(2) 0.0099(19) 0.0202(18) 0.0105(18) C14 0.043(2) 0.031(2) 0.035(2) -0.0045(17) 0.0040(18) 0.0009(17) N2 0.037(2) 0.050(2) 0.059(2) -0.0075(18) -0.0042(18) 0.0081(17) N6 0.048(2) 0.063(3) 0.061(3) 0.002(2) 0.0195(19) -0.006(2) C30 0.045(2) 0.036(2) 0.035(2) 0.0028(17) 0.0142(18) -0.0056(18) C2 0.057(3) 0.050(3) 0.049(3) 0.004(2) 0.015(2) 0.014(2) C7 0.040(3) 0.049(3) 0.076(3) 0.006(2) 0.015(2) 0.011(2) C9 0.055(3) 0.037(2) 0.031(2) -0.0005(17) 0.0061(19) -0.0003(19) N5 0.067(3) 0.050(2) 0.054(2) 0.0064(19) 0.009(2) 0.020(2) C6 0.037(2) 0.036(2) 0.049(2) 0.0023(19) 0.0018(19) 0.0071(18) C35 0.046(3) 0.050(3) 0.040(2) -0.0035(19) 0.0110(19) 0.001(2) C17 0.043(3) 0.111(5) 0.077(4) 0.018(3) 0.028(3) 0.019(3) C4 0.067(3) 0.051(3) 0.059(3) 0.012(2) -0.002(3) 0.019(2) C36 0.066(3) 0.057(3) 0.031(2) 0.003(2) 0.001(2) -0.008(2) C8 0.060(3) 0.051(3) 0.038(2) 0.001(2) 0.022(2) 0.000(2) C34 0.054(3) 0.050(3) 0.060(3) -0.005(2) 0.023(2) 0.006(2) C32 0.082(4) 0.046(3) 0.042(3) -0.006(2) 0.018(2) -0.009(2) C40 0.035(3) 0.062(3) 0.068(3) 0.011(3) 0.013(2) 0.006(2) C41 0.063(3) 0.055(3) 0.033(2) 0.005(2) 0.001(2) 0.007(2) C38 0.056(3) 0.074(4) 0.081(4) -0.009(3) -0.016(3) 0.027(3) C33 0.082(4) 0.046(3) 0.055(3) -0.011(2) 0.033(3) -0.002(3) C5 0.048(3) 0.053(3) 0.070(3) 0.008(2) 0.005(2) 0.017(2) C13 0.046(3) 0.053(3) 0.049(3) -0.003(2) 0.011(2) 0.005(2) C3 0.070(3) 0.051(3) 0.048(3) 0.009(2) 0.014(2) 0.010(2) O5 0.192(5) 0.064(3) 0.088(3) -0.003(2) -0.009(3) 0.055(3) C12 0.044(3) 0.067(3) 0.053(3) -0.007(2) -0.007(2) 0.014(2) C10 0.088(4) 0.052(3) 0.035(2) 0.003(2) 0.010(2) 0.010(3) C37 0.080(4) 0.113(5) 0.080(4) 0.007(4) -0.021(3) 0.041(4) O6 0.084(3) 0.110(4) 0.193(5) 0.074(4) 0.035(3) -0.012(3) C11 0.069(3) 0.065(3) 0.041(3) -0.003(2) -0.016(2) 0.020(3) C15 0.056(3) 0.101(4) 0.063(3) 0.008(3) 0.034(3) 0.009(3) C16 0.064(4) 0.125(5) 0.090(5) -0.001(4) 0.044(3) 0.023(4) C39 0.067(4) 0.111(5) 0.061(3) 0.015(3) -0.019(3) 0.024(3) O3 0.0414(16) 0.0468(16) 0.0422(16) 0.0085(13) 0.0114(13) 0.0157(13) O1 0.0350(15) 0.0569(18) 0.0321(15) -0.0045(13) 0.0073(12) 0.0021(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 C47 O2 1.333(4) . ? C47 C50 1.391(6) . ? C47 C46 1.404(6) . ? C46 C53 1.411(6) . ? C46 C45 1.427(6) . ? C45 N2 1.287(6) . ? C50 C51 1.385(6) . ? C51 C52 1.371(7) . ? C53 C52 1.354(7) . ? Cu1 O4 1.921(2) . ? Cu1 O3 1.938(3) . ? Cu1 N3 1.957(3) . ? Cu1 N4 1.981(3) . ? Cu2 O2 1.914(3) . ? Cu2 O1 1.925(3) . ? Cu2 N2 1.956(4) . ? Cu2 N1 1.959(4) . ? Mn1 N5 2.092(4) . ? Mn1 N6 2.107(4) . ? Mn1 O4 2.228(3) . ? Mn1 O1 2.268(3) . ? Mn1 O2 2.276(3) . ? Mn1 O3 2.346(3) . ? C31 C32 1.410(6) . ? C31 C30 1.421(5) . ? C31 C36 1.428(6) . ? O4 C14 1.323(4) . ? N4 C8 1.275(5) . ? N4 C15 1.479(5) . ? N1 C36 1.284(6) . ? N1 C39 1.477(6) . ? C1 O3 1.323(4) . ? C1 C2 1.394(6) . ? C1 C6 1.397(5) . ? N3 C7 1.276(5) . ? N3 C17 1.479(5) . ? C14 C13 1.401(5) . ? C14 C9 1.403(5) . ? N2 C38 1.490(6) . ? N6 C40 1.137(6) . ? C30 O1 1.331(4) . ? C30 C35 1.387(5) . ? C2 C3 1.385(6) . ? C7 C6 1.440(6) . ? C9 C10 1.396(6) . ? C9 C8 1.436(6) . ? N5 C41 1.137(5) . ? C6 C5 1.401(6) . ? C35 C34 1.371(5) . ? C17 C16 1.419(7) . ? C4 C5 1.363(6) . ? C4 C3 1.375(6) . ? C34 C33 1.390(6) . ? C32 C33 1.352(7) . ? C40 O6 1.177(6) . ? C41 O5 1.191(6) . ? C38 C37 1.513(7) . ? C13 C12 1.376(6) . ? C12 C11 1.382(6) . ? C10 C11 1.369(6) . ? C37 C39 1.447(8) . ? C15 C16 1.439(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C47 C50 119.3(4) . . ? O2 C47 C46 122.1(4) . . ? C50 C47 C46 118.6(4) . . ? C47 C46 C53 119.2(5) . . ? C47 C46 C45 123.0(4) . . ? C53 C46 C45 117.7(4) . . ? N2 C45 C46 127.8(4) . . ? C51 C50 C47 120.4(5) . . ? C52 C51 C50 120.8(5) . . ? C52 C53 C46 120.9(5) . . ? C53 C52 C51 120.0(5) . . ? O4 Cu1 O3 78.60(10) . . ? O4 Cu1 N3 169.15(13) . . ? O3 Cu1 N3 92.48(13) . . ? O4 Cu1 N4 92.07(12) . . ? O3 Cu1 N4 169.28(13) . . ? N3 Cu1 N4 97.34(14) . . ? O2 Cu2 O1 81.10(11) . . ? O2 Cu2 N2 92.43(14) . . ? O1 Cu2 N2 167.19(13) . . ? O2 Cu2 N1 166.66(14) . . ? O1 Cu2 N1 91.56(13) . . ? N2 Cu2 N1 96.81(15) . . ? N5 Mn1 N6 103.96(16) . . ? N5 Mn1 O4 93.60(12) . . ? N6 Mn1 O4 101.11(13) . . ? N5 Mn1 O1 97.19(13) . . ? N6 Mn1 O1 92.00(13) . . ? O4 Mn1 O1 160.51(9) . . ? N5 Mn1 O2 94.23(13) . . ? N6 Mn1 O2 153.68(13) . . ? O4 Mn1 O2 96.49(9) . . ? O1 Mn1 O2 66.63(9) . . ? N5 Mn1 O3 153.86(12) . . ? N6 Mn1 O3 94.69(13) . . ? O4 Mn1 O3 64.55(9) . . ? O1 Mn1 O3 100.34(9) . . ? O2 Mn1 O3 75.38(10) . . ? C32 C31 C30 118.5(4) . . ? C32 C31 C36 118.6(4) . . ? C30 C31 C36 122.5(4) . . ? C14 O4 Cu1 129.0(2) . . ? C14 O4 Mn1 126.9(2) . . ? Cu1 O4 Mn1 103.27(11) . . ? C47 O2 Cu2 126.6(3) . . ? C47 O2 Mn1 130.6(2) . . ? Cu2 O2 Mn1 101.89(11) . . ? C8 N4 C15 115.0(4) . . ? C8 N4 Cu1 122.8(3) . . ? C15 N4 Cu1 122.1(3) . . ? C36 N1 C39 116.7(4) . . ? C36 N1 Cu2 120.6(3) . . ? C39 N1 Cu2 122.6(3) . . ? O3 C1 C2 119.4(4) . . ? O3 C1 C6 122.5(4) . . ? C2 C1 C6 118.1(4) . . ? C7 N3 C17 114.6(4) . . ? C7 N3 Cu1 124.1(3) . . ? C17 N3 Cu1 121.2(3) . . ? O4 C14 C13 120.4(3) . . ? O4 C14 C9 121.8(4) . . ? C13 C14 C9 117.8(4) . . ? C45 N2 C38 116.7(4) . . ? C45 N2 Cu2 123.2(3) . . ? C38 N2 Cu2 120.0(3) . . ? C40 N6 Mn1 156.6(4) . . ? O1 C30 C35 120.6(3) . . ? O1 C30 C31 121.3(4) . . ? C35 C30 C31 118.1(4) . . ? C3 C2 C1 120.9(4) . . ? N3 C7 C6 128.6(4) . . ? C10 C9 C14 119.3(4) . . ? C10 C9 C8 118.5(4) . . ? C14 C9 C8 122.2(4) . . ? C41 N5 Mn1 165.2(4) . . ? C1 C6 C5 119.4(4) . . ? C1 C6 C7 123.0(4) . . ? C5 C6 C7 117.6(4) . . ? C34 C35 C30 121.4(4) . . ? C16 C17 N3 114.2(4) . . ? C5 C4 C3 118.5(4) . . ? N1 C36 C31 128.2(4) . . ? N4 C8 C9 129.8(4) . . ? C35 C34 C33 121.0(4) . . ? C33 C32 C31 122.1(4) . . ? N6 C40 O6 179.2(6) . . ? N5 C41 O5 179.0(6) . . ? N2 C38 C37 110.4(4) . . ? C32 C33 C34 118.8(4) . . ? C4 C5 C6 122.1(4) . . ? C12 C13 C14 121.6(4) . . ? C4 C3 C2 121.1(4) . . ? C13 C12 C11 120.4(4) . . ? C11 C10 C9 122.0(4) . . ? C39 C37 C38 115.7(6) . . ? C10 C11 C12 118.8(4) . . ? C16 C15 N4 116.2(4) . . ? C17 C16 C15 120.7(5) . . ? C37 C39 N1 114.4(5) . . ? C1 O3 Cu1 128.6(2) . . ? C1 O3 Mn1 126.7(2) . . ? Cu1 O3 Mn1 98.61(10) . . ? C30 O1 Cu2 124.8(2) . . ? C30 O1 Mn1 128.7(2) . . ? Cu2 O1 Mn1 101.83(10) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.792 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 951182' ####################################################################### # # 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_4_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 Mn N6 O10' _chemical_formula_weight 866.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.135(5) _cell_length_b 11.609(5) _cell_length_c 16.358(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 100.173(5) _cell_angle_gamma 90.000(5) _cell_volume 1707.5(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11241 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.3 _exptl_crystal_description PLATE _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 882 _exptl_absorpt_coefficient_mu 1.667 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.8922 _exptl_absorpt_correction_T_max 0.9517 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11241 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.31 _reflns_number_total 3049 _reflns_number_gt 2176 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows (Farrugia, 1997)' _computing_publication_material 'Platon99 (Spek, 1999)' _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^)+(0.0845P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3049 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 0.73941(6) 0.18119(5) 0.06206(3) 0.0368(2) Uani 1 1 d . . . Mn1 Mn 0.5000 0.0000 0.0000 0.0340(3) Uani 1 2 d S . . O2 O 0.6953(3) 0.0761(3) -0.03193(18) 0.0383(8) Uani 1 1 d . . . O1 O 0.6221(3) 0.0710(3) 0.11236(18) 0.0383(8) Uani 1 1 d . . . O4 O 0.6309(4) -0.1611(3) 0.0351(2) 0.0521(9) Uani 1 1 d . . . O3 O 0.4740(4) -0.2977(3) -0.0077(2) 0.0590(11) Uani 1 1 d . . . N1 N 0.7485(4) 0.2840(3) 0.1575(3) 0.0403(10) Uani 1 1 d . . . N2 N 0.9000(4) 0.2535(3) 0.0147(2) 0.0401(9) Uani 1 1 d . . . N3 N 0.6004(5) -0.2664(4) 0.0249(2) 0.0449(10) Uani 1 1 d . . . O5 O 0.6990(5) -0.3375(3) 0.0480(3) 0.0794(14) Uani 1 1 d . . . C13 C 0.9286(5) 0.0933(4) -0.0789(3) 0.0392(11) Uani 1 1 d . . . C8 C 0.7920(5) 0.0355(4) -0.0772(3) 0.0341(10) Uani 1 1 d . . . C1 C 0.6274(5) 0.0538(4) 0.1937(3) 0.0363(11) Uani 1 1 d . . . C12 C 1.0245(5) 0.0476(5) -0.1290(3) 0.0475(13) Uani 1 1 d . . . H12 H 1.1147 0.0841 -0.1300 0.057 Uiso 1 1 calc R . . C10 C 0.8559(6) -0.1046(5) -0.1745(3) 0.0500(13) Uani 1 1 d . . . H14 H 0.8317 -0.1704 -0.2065 0.060 Uiso 1 1 calc R . . C6 C 0.6659(5) 0.1443(4) 0.2508(3) 0.0389(11) Uani 1 1 d . . . C9 C 0.7586(5) -0.0630(4) -0.1256(3) 0.0403(11) Uani 1 1 d . . . H9 H 0.6694 -0.1014 -0.1251 0.048 Uiso 1 1 calc R . . C7 C 0.7134(5) 0.2576(4) 0.2271(3) 0.0448(12) Uani 1 1 d . . . H7 H 0.7186 0.3160 0.2664 0.054 Uiso 1 1 calc R . . C16 C 0.9477(6) 0.4066(5) 0.1246(4) 0.0582(15) Uani 1 1 d . . . H16A H 0.9874 0.4840 0.1337 0.070 Uiso 1 1 calc R . . H16B H 1.0112 0.3557 0.1624 0.070 Uiso 1 1 calc R . . C2 C 0.5931(5) -0.0530(5) 0.2230(3) 0.0468(13) Uani 1 1 d . . . H2 H 0.5704 -0.1141 0.1861 0.056 Uiso 1 1 calc R . . C15 C 0.7942(6) 0.4045(4) 0.1462(3) 0.0525(14) Uani 1 1 d . . . H15A H 0.7936 0.4477 0.1969 0.063 Uiso 1 1 calc R . . H15B H 0.7242 0.4404 0.1020 0.063 Uiso 1 1 calc R . . C5 C 0.6589(6) 0.1247(5) 0.3346(3) 0.0570(15) Uani 1 1 d . . . H5 H 0.6794 0.1852 0.3722 0.068 Uiso 1 1 calc R . . C14 C 0.9687(5) 0.2006(4) -0.0363(3) 0.0434(13) Uani 1 1 d . . . H10 H 1.0548 0.2357 -0.0470 0.052 Uiso 1 1 calc R . . C3 C 0.5924(6) -0.0695(5) 0.3065(3) 0.0597(16) Uani 1 1 d . . . H3 H 0.5711 -0.1421 0.3253 0.072 Uiso 1 1 calc R . . C11 C 0.9894(6) -0.0486(5) -0.1759(3) 0.0513(14) Uani 1 1 d . . . H11 H 1.0547 -0.0765 -0.2089 0.062 Uiso 1 1 calc R . . C17 C 0.9556(6) 0.3716(5) 0.0372(3) 0.0577(15) Uani 1 1 d . . . H17A H 0.8982 0.4259 -0.0006 0.069 Uiso 1 1 calc R . . H17B H 1.0582 0.3767 0.0294 0.069 Uiso 1 1 calc R . . C4 C 0.6231(6) 0.0203(6) 0.3626(3) 0.0634(17) Uani 1 1 d . . . H4 H 0.6192 0.0092 0.4185 0.076 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 0.0373(4) 0.0339(4) 0.0381(4) -0.0034(2) 0.0035(3) -0.0108(2) Mn1 0.0282(5) 0.0367(6) 0.0362(6) -0.0061(4) 0.0027(4) -0.0082(4) O2 0.0347(18) 0.042(2) 0.0396(18) -0.0065(15) 0.0119(14) -0.0077(14) O1 0.0419(19) 0.0389(19) 0.0334(18) -0.0057(14) 0.0050(14) -0.0108(14) O4 0.045(2) 0.034(2) 0.073(2) -0.0081(18) -0.0027(18) -0.0032(16) O3 0.043(2) 0.048(2) 0.077(3) -0.0024(19) -0.0126(19) -0.0091(17) N1 0.036(2) 0.032(2) 0.052(3) -0.0046(19) 0.0029(19) -0.0044(17) N2 0.037(2) 0.036(2) 0.046(2) 0.0077(19) 0.0029(18) -0.0103(18) N3 0.043(2) 0.042(3) 0.049(2) 0.003(2) 0.0045(19) 0.002(2) O5 0.053(2) 0.047(2) 0.131(4) 0.011(2) -0.003(2) 0.005(2) C13 0.029(2) 0.046(3) 0.040(3) 0.012(2) 0.002(2) 0.002(2) C8 0.026(2) 0.044(3) 0.032(2) 0.008(2) 0.0034(19) 0.002(2) C1 0.027(2) 0.045(3) 0.036(3) 0.000(2) 0.0040(19) -0.004(2) C12 0.028(3) 0.070(4) 0.046(3) 0.013(3) 0.010(2) 0.006(2) C10 0.050(3) 0.053(3) 0.045(3) -0.001(2) 0.004(2) 0.012(3) C6 0.029(2) 0.051(3) 0.036(3) -0.003(2) 0.0027(19) -0.002(2) C9 0.038(3) 0.040(3) 0.042(3) -0.001(2) 0.003(2) 0.001(2) C7 0.038(3) 0.043(3) 0.052(3) -0.016(3) 0.002(2) 0.003(2) C16 0.057(4) 0.038(3) 0.078(4) -0.001(3) 0.004(3) -0.025(3) C2 0.047(3) 0.050(3) 0.043(3) 0.001(3) 0.007(2) -0.014(3) C15 0.059(3) 0.029(3) 0.066(4) -0.010(2) 0.001(3) -0.008(2) C5 0.050(3) 0.077(4) 0.045(3) -0.009(3) 0.009(2) -0.011(3) C14 0.029(3) 0.056(3) 0.045(3) 0.013(3) 0.006(2) -0.009(2) C3 0.050(3) 0.070(4) 0.060(4) 0.016(3) 0.010(3) -0.011(3) C11 0.038(3) 0.067(4) 0.049(3) 0.005(3) 0.011(2) 0.017(3) C17 0.058(4) 0.048(3) 0.064(4) -0.002(3) 0.001(3) -0.021(3) C4 0.055(4) 0.098(5) 0.037(3) 0.004(3) 0.007(3) -0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.942(3) . ? Cu1 O2 1.948(3) . ? Cu1 N1 1.956(4) . ? Cu1 N2 1.964(4) . ? Cu1 O3 2.410(4) 3_655 ? Cu1 Mn1 3.0747(11) . ? Mn1 O2 2.137(3) . ? Mn1 O2 2.137(3) 3_655 ? Mn1 O1 2.139(3) 3_655 ? Mn1 O1 2.139(3) . ? Mn1 O4 2.240(3) 3_655 ? Mn1 O4 2.240(3) . ? Mn1 Cu1 3.0747(11) 3_655 ? O2 C8 1.334(5) . ? O1 C1 1.338(5) . ? O4 N3 1.258(5) . ? O3 N3 1.237(5) . ? O3 Cu1 2.410(4) 3_655 ? N1 C7 1.273(6) . ? N1 C15 1.480(6) . ? N2 C14 1.286(6) . ? N2 C17 1.485(6) . ? N3 O5 1.231(5) . ? C13 C12 1.405(7) . ? C13 C8 1.422(6) . ? C13 C14 1.442(7) . ? C8 C9 1.394(6) . ? C1 C2 1.385(7) . ? C1 C6 1.409(6) . ? C12 C11 1.361(7) . ? C10 C9 1.383(7) . ? C10 C11 1.386(7) . ? C6 C5 1.403(7) . ? C6 C7 1.459(7) . ? C16 C17 1.500(8) . ? C16 C15 1.505(8) . ? C2 C3 1.380(7) . ? C5 C4 1.356(8) . ? C3 C4 1.385(8) . ? 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 O2 82.48(12) . . ? O1 Cu1 N1 90.73(15) . . ? O2 Cu1 N1 170.41(14) . . ? O1 Cu1 N2 162.71(15) . . ? O2 Cu1 N2 91.23(15) . . ? N1 Cu1 N2 97.14(17) . . ? O1 Cu1 O3 93.15(13) . 3_655 ? O2 Cu1 O3 91.09(13) . 3_655 ? N1 Cu1 O3 82.49(14) . 3_655 ? N2 Cu1 O3 103.10(15) . 3_655 ? O1 Cu1 Mn1 43.60(8) . . ? O2 Cu1 Mn1 43.54(9) . . ? N1 Cu1 Mn1 127.49(11) . . ? N2 Cu1 Mn1 134.40(12) . . ? O3 Cu1 Mn1 77.30(9) 3_655 . ? O2 Mn1 O2 180.0(2) . 3_655 ? O2 Mn1 O1 106.28(11) . 3_655 ? O2 Mn1 O1 73.72(11) 3_655 3_655 ? O2 Mn1 O1 73.72(11) . . ? O2 Mn1 O1 106.28(11) 3_655 . ? O1 Mn1 O1 180.00(18) 3_655 . ? O2 Mn1 O4 91.31(13) . 3_655 ? O2 Mn1 O4 88.69(13) 3_655 3_655 ? O1 Mn1 O4 85.86(12) 3_655 3_655 ? O1 Mn1 O4 94.14(12) . 3_655 ? O2 Mn1 O4 88.69(13) . . ? O2 Mn1 O4 91.31(13) 3_655 . ? O1 Mn1 O4 94.14(12) 3_655 . ? O1 Mn1 O4 85.86(12) . . ? O4 Mn1 O4 180.0(3) 3_655 . ? O2 Mn1 Cu1 141.08(8) . 3_655 ? O2 Mn1 Cu1 38.92(8) 3_655 3_655 ? O1 Mn1 Cu1 38.77(8) 3_655 3_655 ? O1 Mn1 Cu1 141.23(8) . 3_655 ? O4 Mn1 Cu1 99.81(9) 3_655 3_655 ? O4 Mn1 Cu1 80.19(9) . 3_655 ? O2 Mn1 Cu1 38.92(8) . . ? O2 Mn1 Cu1 141.08(8) 3_655 . ? O1 Mn1 Cu1 141.23(8) 3_655 . ? O1 Mn1 Cu1 38.77(8) . . ? O4 Mn1 Cu1 80.19(9) 3_655 . ? O4 Mn1 Cu1 99.81(9) . . ? Cu1 Mn1 Cu1 180.000(15) 3_655 . ? C8 O2 Cu1 126.4(3) . . ? C8 O2 Mn1 130.7(3) . . ? Cu1 O2 Mn1 97.54(13) . . ? C1 O1 Cu1 126.4(3) . . ? C1 O1 Mn1 135.9(3) . . ? Cu1 O1 Mn1 97.63(13) . . ? N3 O4 Mn1 133.0(3) . . ? N3 O3 Cu1 128.8(3) . 3_655 ? C7 N1 C15 117.5(4) . . ? C7 N1 Cu1 125.8(3) . . ? C15 N1 Cu1 116.7(3) . . ? C14 N2 C17 114.7(4) . . ? C14 N2 Cu1 122.4(3) . . ? C17 N2 Cu1 122.9(3) . . ? O5 N3 O3 120.8(4) . . ? O5 N3 O4 118.5(4) . . ? O3 N3 O4 120.7(4) . . ? C12 C13 C8 118.3(5) . . ? C12 C13 C14 118.5(4) . . ? C8 C13 C14 123.1(4) . . ? O2 C8 C9 120.3(4) . . ? O2 C8 C13 120.9(4) . . ? C9 C8 C13 118.7(4) . . ? O1 C1 C2 120.5(4) . . ? O1 C1 C6 120.6(4) . . ? C2 C1 C6 118.9(4) . . ? C11 C12 C13 122.0(5) . . ? C9 C10 C11 120.2(5) . . ? C5 C6 C1 118.6(5) . . ? C5 C6 C7 118.3(5) . . ? C1 C6 C7 123.2(4) . . ? C10 C9 C8 121.1(5) . . ? N1 C7 C6 126.1(4) . . ? C17 C16 C15 115.0(5) . . ? C3 C2 C1 120.5(5) . . ? N1 C15 C16 109.9(4) . . ? C4 C5 C6 122.1(5) . . ? N2 C14 C13 128.0(4) . . ? C2 C3 C4 121.0(5) . . ? C12 C11 C10 119.7(5) . . ? N2 C17 C16 114.5(4) . . ? C5 C4 C3 118.8(5) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.967 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 951183' ####################################################################### # # 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_5_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H46 Cl4 Cu2 Mn N4 O10' _chemical_formula_weight 1186.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.532(5) _cell_length_b 17.981(5) _cell_length_c 26.275(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4976(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32429 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 24.9 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2420 _exptl_absorpt_coefficient_mu 1.375 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8980 _exptl_absorpt_correction_T_max 0.9471 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32429 _diffrn_reflns_av_R_equivalents 0.0925 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 24.93 _reflns_number_total 4340 _reflns_number_gt 2751 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows (Farrugia, 1997)' _computing_publication_material 'Platon99 (Spek, 1999)' _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^)+(0.0851P)^2^+6.5565P] 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 4340 _refine_ls_number_parameters 322 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1022 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1779 _refine_ls_wR_factor_gt 0.1548 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.023 _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 Mn1 Mn 0.0000 0.0000 0.0000 0.0465(3) Uani 1 2 d S . . Cu1 Cu 0.17818(6) 0.11201(4) 0.05577(3) 0.0511(3) Uani 1 1 d . . . C11 C -0.0855(5) 0.1627(3) 0.0378(2) 0.0502(14) Uani 1 1 d . . . C12 C -0.1921(6) 0.1621(3) 0.0055(2) 0.0600(16) Uani 1 1 d . . . H12 H -0.1995 0.1256 -0.0194 0.072 Uiso 1 1 calc R . . C13 C -0.2855(6) 0.2150(4) 0.0105(3) 0.0636(17) Uani 1 1 d . . . H13 H -0.3549 0.2139 -0.0113 0.076 Uiso 1 1 calc R . . C14 C -0.2785(6) 0.2704(4) 0.0475(3) 0.0674(18) Uani 1 1 d . . . H14 H -0.3432 0.3052 0.0511 0.081 Uiso 1 1 calc R . . C15 C -0.1744(6) 0.2720(3) 0.0781(3) 0.0692(18) Uani 1 1 d . . . H15 H -0.1688 0.3087 0.1029 0.083 Uiso 1 1 calc R . . C16 C -0.0743(5) 0.2199(3) 0.0734(2) 0.0548(15) Uani 1 1 d . . . C17 C 0.0326(6) 0.2268(3) 0.1070(2) 0.0611(16) Uani 1 1 d . . . H17 H 0.0248 0.2623 0.1325 0.073 Uiso 1 1 calc R . . C18 C 0.2281(7) 0.2071(5) 0.1469(3) 0.084(2) Uani 1 1 d . . . H18A H 0.2289 0.1663 0.1710 0.101 Uiso 1 1 calc R . . H18B H 0.2014 0.2515 0.1650 0.101 Uiso 1 1 calc R . . C19 C 0.3605(7) 0.2187(4) 0.1264(3) 0.085(2) Uani 1 1 d . . . H19A H 0.3567 0.2548 0.0990 0.102 Uiso 1 1 calc R . . H19B H 0.4128 0.2396 0.1532 0.102 Uiso 1 1 calc R . . C20 C 0.4235(6) 0.1499(4) 0.1069(3) 0.076(2) Uani 1 1 d . . . H20A H 0.5124 0.1603 0.1003 0.092 Uiso 1 1 calc R . . H20B H 0.4193 0.1115 0.1328 0.092 Uiso 1 1 calc R . . C21 C 0.4405(6) 0.1028(3) 0.0242(3) 0.0616(17) Uani 1 1 d . . . H21 H 0.5264 0.1109 0.0300 0.074 Uiso 1 1 calc R . . C22 C 0.4087(5) 0.0704(3) -0.0231(2) 0.0524(14) Uani 1 1 d . . . C23 C 0.5033(6) 0.0683(3) -0.0607(3) 0.0626(17) Uani 1 1 d . . . H23 H 0.5832 0.0875 -0.0534 0.075 Uiso 1 1 calc R . . C24 C 0.4815(6) 0.0391(4) -0.1074(3) 0.0699(18) Uani 1 1 d . . . H24 H 0.5447 0.0404 -0.1322 0.084 Uiso 1 1 calc R . . C25 C 0.3654(7) 0.0075(4) -0.1182(3) 0.0719(18) Uani 1 1 d . . . H25 H 0.3506 -0.0136 -0.1499 0.086 Uiso 1 1 calc R . . C26 C 0.2713(6) 0.0073(4) -0.0818(3) 0.0624(16) Uani 1 1 d . . . H26 H 0.1938 -0.0148 -0.0895 0.075 Uiso 1 1 calc R . . C27 C 0.2881(5) 0.0391(3) -0.0335(2) 0.0502(14) Uani 1 1 d . . . C31 C 0.0877(5) -0.0303(3) 0.1130(2) 0.0547(15) Uani 1 1 d . . . C32 C 0.0640(6) -0.0724(3) 0.1613(2) 0.0601(16) Uani 1 1 d . . . C33 C -0.0404(7) -0.1217(4) 0.1627(3) 0.082(2) Uani 1 1 d . . . H33 H -0.0923 -0.1294 0.1346 0.098 Uiso 1 1 calc R . . C34 C -0.0612(10) -0.1579(5) 0.2084(4) 0.113(3) Uani 1 1 d . . . H34 H -0.1310 -0.1891 0.2120 0.136 Uiso 1 1 calc R . . C35 C 0.0211(15) -0.1479(7) 0.2487(4) 0.141(5) Uani 1 1 d . . . H35 H 0.0072 -0.1748 0.2784 0.170 Uiso 1 1 calc R . . C36 C 0.1177(11) -0.1023(6) 0.2469(4) 0.114(3) Uani 1 1 d . . . H36 H 0.1708 -0.0968 0.2749 0.137 Uiso 1 1 calc R . . C37 C 0.1397(8) -0.0628(4) 0.2030(3) 0.078(2) Uani 1 1 d . . . N1 N 0.1368(5) 0.1909(3) 0.10649(18) 0.0591(13) Uani 1 1 d . . . N2 N 0.3643(5) 0.1224(3) 0.0603(2) 0.0559(13) Uani 1 1 d . . . O1 O 0.0000(3) 0.1094(2) 0.03389(16) 0.0564(10) Uani 1 1 d . . . O2 O 0.1966(3) 0.0403(2) 0.00024(14) 0.0514(10) Uani 1 1 d . . . O3 O 0.1693(4) 0.0219(3) 0.11494(16) 0.0735(12) Uani 1 1 d . . . O4 O 0.0273(4) -0.0470(2) 0.07450(16) 0.0643(11) Uani 1 1 d . . . O5 O 0.2386(6) -0.0167(4) 0.2023(2) 0.1111(19) Uani 1 1 d . . . H5 H 0.2352 0.0094 0.1767 0.167 Uiso 1 1 calc R . . C1A C -0.131(5) 0.0802(14) 0.226(3) 0.124(5) Uiso 0.28(7) 1 d PD A 1 H1A1 H -0.1865 0.0614 0.2528 0.148 Uiso 0.28(7) 1 calc PR A 1 H1A2 H -0.1116 0.0399 0.2030 0.148 Uiso 0.28(7) 1 calc PR A 1 C1B C -0.104(2) 0.0870(10) 0.2072(13) 0.124(5) Uiso 0.72(7) 1 d PD A 2 H1B1 H -0.0606 0.0711 0.1765 0.148 Uiso 0.72(7) 1 calc PR A 2 H1B2 H -0.1504 0.0447 0.2207 0.148 Uiso 0.72(7) 1 calc PR A 2 Cl1 Cl 0.0084(4) 0.1173(2) 0.25241(16) 0.1895(16) Uani 1 1 d D . . Cl2 Cl -0.2062(4) 0.1555(2) 0.19297(18) 0.2080(18) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0400(6) 0.0490(7) 0.0505(7) -0.0055(6) -0.0020(5) -0.0089(5) Cu1 0.0409(4) 0.0558(4) 0.0567(5) -0.0056(3) -0.0054(3) -0.0083(3) C11 0.043(3) 0.046(3) 0.061(4) 0.002(3) 0.005(3) -0.007(3) C12 0.057(4) 0.059(4) 0.064(4) 0.004(3) -0.002(3) -0.002(3) C13 0.044(3) 0.068(4) 0.080(5) 0.012(4) -0.003(3) -0.005(3) C14 0.049(4) 0.053(4) 0.101(5) 0.012(4) 0.010(4) 0.002(3) C15 0.065(4) 0.045(3) 0.097(5) -0.001(3) 0.022(4) 0.003(3) C16 0.056(4) 0.050(3) 0.059(4) 0.004(3) 0.008(3) -0.006(3) C17 0.069(4) 0.058(4) 0.056(4) -0.018(3) 0.001(3) -0.009(3) C18 0.086(5) 0.098(6) 0.069(5) -0.025(4) -0.009(4) -0.001(4) C19 0.080(5) 0.089(5) 0.085(5) -0.020(4) -0.033(4) -0.026(4) C20 0.055(4) 0.089(5) 0.085(5) -0.010(4) -0.020(4) -0.015(4) C21 0.037(3) 0.064(4) 0.084(5) 0.017(4) -0.005(3) -0.007(3) C22 0.039(3) 0.056(3) 0.062(4) 0.014(3) -0.002(3) -0.001(3) C23 0.038(3) 0.067(4) 0.083(5) 0.011(4) 0.008(3) -0.003(3) C24 0.051(4) 0.084(5) 0.075(5) 0.012(4) 0.021(4) 0.012(3) C25 0.068(4) 0.087(5) 0.061(4) -0.004(4) 0.011(4) 0.015(4) C26 0.043(3) 0.073(4) 0.070(4) -0.010(4) 0.002(3) 0.001(3) C27 0.038(3) 0.050(3) 0.063(4) 0.007(3) 0.000(3) -0.001(2) C31 0.046(3) 0.056(3) 0.062(4) -0.007(3) -0.003(3) 0.003(3) C32 0.073(4) 0.052(4) 0.056(4) 0.011(3) 0.010(3) 0.010(3) C33 0.085(5) 0.064(4) 0.096(6) 0.017(4) 0.031(4) 0.002(4) C34 0.134(9) 0.087(6) 0.118(8) 0.024(6) 0.054(7) -0.018(6) C35 0.195(14) 0.151(11) 0.079(7) 0.046(7) 0.039(8) 0.018(10) C36 0.133(8) 0.141(9) 0.068(6) 0.024(6) 0.012(6) -0.007(7) C37 0.085(5) 0.079(5) 0.069(5) 0.002(4) -0.008(4) 0.006(4) N1 0.053(3) 0.071(3) 0.053(3) -0.011(3) -0.008(2) -0.006(3) N2 0.044(3) 0.058(3) 0.066(3) 0.002(3) -0.016(3) -0.008(2) O1 0.042(2) 0.054(2) 0.074(3) -0.012(2) -0.0042(19) -0.0017(19) O2 0.038(2) 0.062(2) 0.054(2) -0.0109(19) 0.0039(18) -0.0099(17) O3 0.072(3) 0.079(3) 0.069(3) 0.011(2) -0.017(2) -0.018(2) O4 0.065(3) 0.069(3) 0.059(3) 0.003(2) -0.007(2) -0.012(2) O5 0.108(4) 0.135(5) 0.091(4) 0.007(4) -0.036(4) -0.011(4) Cl1 0.165(3) 0.231(4) 0.173(3) -0.007(3) 0.012(3) 0.004(3) Cl2 0.206(4) 0.194(4) 0.225(4) 0.067(3) -0.009(3) -0.015(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O4 2.152(4) 5 ? Mn1 O4 2.152(4) . ? Mn1 O1 2.160(4) . ? Mn1 O1 2.160(4) 5 ? Mn1 O2 2.194(3) . ? Mn1 O2 2.194(3) 5 ? Mn1 Cu1 3.1186(9) . ? Mn1 Cu1 3.1186(9) 5 ? Cu1 O2 1.957(4) . ? Cu1 O1 1.963(4) . ? Cu1 N2 1.973(5) . ? Cu1 N1 1.995(5) . ? Cu1 O3 2.247(4) . ? C11 O1 1.319(6) . ? C11 C16 1.397(8) . ? C11 C12 1.406(8) . ? C12 C13 1.375(8) . ? C13 C14 1.392(9) . ? C14 C15 1.360(9) . ? C15 C16 1.416(8) . ? C16 C17 1.435(8) . ? C17 N1 1.273(7) . ? C18 N1 1.462(8) . ? C18 C19 1.510(10) . ? C19 C20 1.494(10) . ? C20 N2 1.460(8) . ? C21 N2 1.292(8) . ? C21 C22 1.411(9) . ? C22 C23 1.405(8) . ? C22 C27 1.416(7) . ? C23 C24 1.354(9) . ? C24 C25 1.378(9) . ? C25 C26 1.377(8) . ? C26 C27 1.404(8) . ? C27 O2 1.308(6) . ? C31 O4 1.231(7) . ? C31 O3 1.275(7) . ? C31 C32 1.499(8) . ? C32 C37 1.366(9) . ? C32 C33 1.413(9) . ? C33 C34 1.382(11) . ? C34 C35 1.379(15) . ? C35 C36 1.307(15) . ? C36 C37 1.374(11) . ? C37 O5 1.332(9) . ? C1A Cl1 1.756(19) . ? C1A Cl2 1.79(2) . ? C1B Cl2 1.678(13) . ? C1B Cl1 1.764(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Mn1 O4 180.0(2) 5 . ? O4 Mn1 O1 90.98(16) 5 . ? O4 Mn1 O1 89.02(16) . . ? O4 Mn1 O1 89.02(16) 5 5 ? O4 Mn1 O1 90.98(16) . 5 ? O1 Mn1 O1 180.0(2) . 5 ? O4 Mn1 O2 89.93(15) 5 . ? O4 Mn1 O2 90.07(15) . . ? O1 Mn1 O2 72.42(13) . . ? O1 Mn1 O2 107.58(13) 5 . ? O4 Mn1 O2 90.07(15) 5 5 ? O4 Mn1 O2 89.93(15) . 5 ? O1 Mn1 O2 107.58(13) . 5 ? O1 Mn1 O2 72.42(13) 5 5 ? O2 Mn1 O2 180.00(18) . 5 ? O4 Mn1 Cu1 104.71(11) 5 . ? O4 Mn1 Cu1 75.29(11) . . ? O1 Mn1 Cu1 38.55(10) . . ? O1 Mn1 Cu1 141.45(10) 5 . ? O2 Mn1 Cu1 38.50(10) . . ? O2 Mn1 Cu1 141.50(10) 5 . ? O4 Mn1 Cu1 75.29(11) 5 5 ? O4 Mn1 Cu1 104.71(11) . 5 ? O1 Mn1 Cu1 141.45(10) . 5 ? O1 Mn1 Cu1 38.55(10) 5 5 ? O2 Mn1 Cu1 141.50(10) . 5 ? O2 Mn1 Cu1 38.50(10) 5 5 ? Cu1 Mn1 Cu1 180.00(3) . 5 ? O2 Cu1 O1 82.00(15) . . ? O2 Cu1 N2 90.52(18) . . ? O1 Cu1 N2 165.9(2) . . ? O2 Cu1 N1 171.30(18) . . ? O1 Cu1 N1 90.21(18) . . ? N2 Cu1 N1 96.3(2) . . ? O2 Cu1 O3 92.58(17) . . ? O1 Cu1 O3 98.39(16) . . ? N2 Cu1 O3 93.85(18) . . ? N1 Cu1 O3 92.37(19) . . ? O2 Cu1 Mn1 44.25(10) . . ? O1 Cu1 Mn1 43.27(11) . . ? N2 Cu1 Mn1 133.43(15) . . ? N1 Cu1 Mn1 129.92(14) . . ? O3 Cu1 Mn1 80.49(11) . . ? O1 C11 C16 121.9(5) . . ? O1 C11 C12 119.6(5) . . ? C16 C11 C12 118.5(5) . . ? C13 C12 C11 120.5(6) . . ? C12 C13 C14 121.6(6) . . ? C15 C14 C13 118.1(6) . . ? C14 C15 C16 122.3(6) . . ? C11 C16 C15 118.8(6) . . ? C11 C16 C17 122.8(5) . . ? C15 C16 C17 118.3(6) . . ? N1 C17 C16 128.8(6) . . ? N1 C18 C19 112.0(6) . . ? C20 C19 C18 114.8(6) . . ? N2 C20 C19 112.2(6) . . ? N2 C21 C22 127.7(5) . . ? C23 C22 C21 117.6(5) . . ? C23 C22 C27 119.3(6) . . ? C21 C22 C27 123.1(6) . . ? C24 C23 C22 121.9(6) . . ? C23 C24 C25 119.7(6) . . ? C26 C25 C24 119.9(7) . . ? C25 C26 C27 122.4(6) . . ? O2 C27 C26 121.8(5) . . ? O2 C27 C22 121.5(5) . . ? C26 C27 C22 116.7(5) . . ? O4 C31 O3 124.2(6) . . ? O4 C31 C32 119.1(6) . . ? O3 C31 C32 116.7(6) . . ? C37 C32 C33 120.8(6) . . ? C37 C32 C31 121.2(6) . . ? C33 C32 C31 118.0(6) . . ? C34 C33 C32 116.2(8) . . ? C35 C34 C33 120.4(9) . . ? C36 C35 C34 122.8(10) . . ? C35 C36 C37 119.1(10) . . ? O5 C37 C32 121.6(7) . . ? O5 C37 C36 117.8(8) . . ? C32 C37 C36 120.6(8) . . ? C17 N1 C18 117.3(5) . . ? C17 N1 Cu1 123.7(4) . . ? C18 N1 Cu1 118.9(4) . . ? C21 N2 C20 116.4(5) . . ? C21 N2 Cu1 123.1(4) . . ? C20 N2 Cu1 120.5(4) . . ? C11 O1 Cu1 127.8(3) . . ? C11 O1 Mn1 133.9(3) . . ? Cu1 O1 Mn1 98.19(15) . . ? C27 O2 Cu1 126.1(3) . . ? C27 O2 Mn1 133.4(3) . . ? Cu1 O2 Mn1 97.24(15) . . ? C31 O3 Cu1 122.1(4) . . ? C31 O4 Mn1 136.0(4) . . ? Cl1 C1A Cl2 105.8(12) . . ? Cl2 C1B Cl1 110.7(8) . . ? C1A Cl1 C1B 19(2) . . ? C1B Cl2 C1A 19(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.687 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 951184'