# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_pnma _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H72 Mn4 N28 O32' _chemical_formula_weight 1893.20 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 15.365(3) _cell_length_b 31.833(6) _cell_length_c 16.779(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8207(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21061 _cell_measurement_theta_min 1.9075 _cell_measurement_theta_max 27.8286 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3888 _exptl_absorpt_coefficient_mu 0.701 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7247 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 ; Saturn724 (4x4 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7356 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7356 _reflns_number_gt 6141 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0817P)^2^+27.0112P] 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 7356 _refine_ls_number_parameters 574 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.2171 _refine_ls_wR_factor_gt 0.2055 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.057 _refine_ls_shift/su_mean 0.002 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 0.30609(5) 0.53456(3) 0.11991(4) 0.0325(2) Uani 1 1 d . . . Mn2 Mn 0.03958(6) 0.59758(3) 0.12753(5) 0.0412(3) Uani 1 1 d U . . C1 C 0.2283(4) 0.60734(19) 0.2124(3) 0.0378(13) Uani 1 1 d . . . C2 C 0.2360(4) 0.65106(19) 0.2486(4) 0.0460(15) Uani 1 1 d . . . H2A H 0.2653 0.6488 0.2996 0.055 Uiso 1 1 calc R . . H2B H 0.2722 0.6682 0.2141 0.055 Uiso 1 1 calc R . . C3 C 0.1503(4) 0.67324(19) 0.2608(4) 0.0479(15) Uani 1 1 d . . . H3A H 0.1238 0.6785 0.2094 0.058 Uiso 1 1 calc R . . H3B H 0.1116 0.6551 0.2907 0.058 Uiso 1 1 calc R . . C4 C 0.3393(11) 0.7500 0.5162(17) 0.190(15) Uani 1 2 d SD . . C5 C 0.2601(12) 0.7260(6) 0.5371(11) 0.113(8) Uani 0.50 1 d PD . . H5 H 0.2598 0.7123 0.5894 0.135 Uiso 1 1 calc R . . C6 C 0.1741(8) 0.7500 0.5125(6) 0.078(3) Uani 1 2 d SD . . H6 H 0.1220 0.7500 0.5461 0.093 Uiso 1 2 calc SR . . C7 C 0.1622(5) 0.7113(2) 0.3871(4) 0.0581(18) Uani 1 1 d . . . C8 C 0.1606(5) 0.7500 0.2599(5) 0.0410(19) Uani 1 2 d S . . C9 C 0.1072(6) 0.6715(3) 0.0310(5) 0.080(2) Uani 1 1 d U . . C10 C 0.1810(8) 0.6483(3) -0.0010(9) 0.149(6) Uani 1 1 d . . . H10A H 0.1609 0.6212 -0.0196 0.179 Uiso 1 1 calc R . . H10B H 0.2224 0.6434 0.0417 0.179 Uiso 1 1 calc R . . C11 C 0.2306(9) 0.6720(3) -0.0735(5) 0.112(4) Uani 1 1 d . . . H11A H 0.2733 0.6530 -0.0964 0.135 Uiso 1 1 calc R . . H11B H 0.1886 0.6787 -0.1148 0.135 Uiso 1 1 calc R . . C12 C 0.4396(8) 0.7500 0.2587(9) 0.101(4) Uani 1 2 d SU . . C13 C 0.3885(9) 0.7500 0.1883(8) 0.116(4) Uani 1 2 d SDU . . H13A H 0.3510 0.7745 0.1904 0.140 Uiso 0.50 1 calc PR . . H13B H 0.3510 0.7255 0.1904 0.140 Uiso 0.50 1 calc PR . . C14 C 0.4309(8) 0.7500 0.1099(8) 0.109(4) Uani 1 2 d SDU . . H14A H 0.4678 0.7254 0.1054 0.131 Uiso 0.50 1 calc PR . . H14B H 0.4678 0.7746 0.1054 0.131 Uiso 0.50 1 calc PR . . C15 C 0.3353(7) 0.7114(4) 0.0141(6) 0.093(3) Uani 1 1 d . . . C16 C 0.2488(10) 0.7500 -0.0821(8) 0.088(4) Uani 1 2 d S . . C17 C -0.1186(4) 0.6134(2) -0.0089(4) 0.0516(16) Uani 1 1 d . . . H17 H -0.1416 0.6328 0.0269 0.062 Uiso 1 1 calc R . . C18 C -0.1574(5) 0.6077(3) -0.0823(5) 0.069(2) Uani 1 1 d . . . H18 H -0.2069 0.6234 -0.0936 0.083 Uiso 1 1 calc R . . C19 C -0.0574(5) 0.5598(3) -0.1176(4) 0.062(2) Uani 1 1 d . . . H19 H -0.0344 0.5410 -0.1544 0.075 Uiso 1 1 calc R . . C20 C -0.0162(4) 0.56450(18) -0.0440(3) 0.0381(13) Uani 1 1 d . . . C21 C 0.0647(3) 0.54292(18) -0.0227(3) 0.0341(12) Uani 1 1 d . . . C22 C 0.1785(3) 0.50669(18) -0.0173(3) 0.0319(12) Uani 1 1 d . . . C23 C 0.2523(3) 0.47898(17) -0.0321(3) 0.0310(12) Uani 1 1 d . . . C24 C 0.2590(4) 0.4494(2) -0.0920(3) 0.0393(14) Uani 1 1 d . . . H24 H 0.2140 0.4456 -0.1283 0.047 Uiso 1 1 calc R . . C25 C 0.3344(4) 0.42534(19) -0.0969(3) 0.0444(15) Uani 1 1 d . . . H25 H 0.3397 0.4050 -0.1363 0.053 Uiso 1 1 calc R . . C26 C 0.4018(3) 0.43170(19) -0.0430(3) 0.0380(13) Uani 1 1 d . . . H26 H 0.4528 0.4160 -0.0464 0.046 Uiso 1 1 calc R . . C27 C 0.3918(3) 0.46153(18) 0.0154(3) 0.0334(12) Uani 1 1 d . . . C28 C 0.4560(3) 0.47217(18) 0.0771(3) 0.0312(12) Uani 1 1 d . . . C29 C 0.5632(3) 0.47458(18) 0.1531(3) 0.0336(12) Uani 1 1 d . . . C30 C 0.6495(3) 0.46688(18) 0.1906(3) 0.0336(12) Uani 1 1 d . . . C31 C 0.7710(4) 0.4276(2) 0.2014(4) 0.0519(17) Uani 1 1 d . . . H31 H 0.8044 0.4046 0.1862 0.062 Uiso 1 1 calc R . . C32 C 0.8035(4) 0.4536(2) 0.2589(4) 0.0470(15) Uani 1 1 d . . . H32 H 0.8571 0.4476 0.2819 0.056 Uiso 1 1 calc R . . C33 C 0.6810(3) 0.49402(17) 0.2482(3) 0.0318(12) Uani 1 1 d . . . H33 H 0.6474 0.5170 0.2633 0.038 Uiso 1 1 calc R . . N1 N 0.1602(3) 0.71350(15) 0.3039(3) 0.0448(12) Uani 1 1 d . . . N2 N 0.1691(5) 0.7500 0.4255(5) 0.056(2) Uani 1 2 d S . . N3 N 0.3651(6) 0.7500 0.0415(6) 0.087(3) Uani 1 2 d S . . N4 N 0.2763(5) 0.7124(3) -0.0472(4) 0.085(2) Uani 1 1 d . . . N5 N -0.0485(3) 0.59143(16) 0.0105(3) 0.0426(12) Uani 1 1 d . . . N6 N -0.1296(4) 0.5818(2) -0.1370(4) 0.074(2) Uani 1 1 d . . . N7 N 0.1079(3) 0.51264(16) -0.0640(2) 0.0364(11) Uani 1 1 d . . . N8 N 0.1044(3) 0.55427(16) 0.0451(3) 0.0368(11) Uani 1 1 d . . . N9 N 0.1792(3) 0.53087(15) 0.0483(2) 0.0348(11) Uani 1 1 d . . . N10 N 0.3184(3) 0.48458(14) 0.0208(2) 0.0319(10) Uani 1 1 d . . . N11 N 0.4376(3) 0.50210(15) 0.1311(2) 0.0327(10) Uani 1 1 d . . . N12 N 0.5077(3) 0.50342(15) 0.1816(2) 0.0324(10) Uani 1 1 d . . . N13 N 0.5344(3) 0.45408(15) 0.0870(2) 0.0315(10) Uani 1 1 d . . . N14 N 0.6942(3) 0.43316(17) 0.1657(3) 0.0455(13) Uani 1 1 d . . . N15 N 0.7590(3) 0.48804(16) 0.2829(3) 0.0377(11) Uani 1 1 d . . . O1 O 0.1540(3) 0.59275(14) 0.2010(2) 0.0475(10) Uani 1 1 d . . . O2 O 0.2985(3) 0.58784(14) 0.1989(2) 0.0460(10) Uani 1 1 d . . . O3W O -0.0508(4) 0.6329(2) 0.1996(5) 0.099(3) Uani 1 1 d . . . H3WA H -0.0899 0.6173 0.2150 0.149 Uiso 1 1 calc R . . O3 O 0.3749(12) 0.7206(5) 0.4767(11) 0.276(9) Uani 1 1 d . . . O4 O 0.1596(5) 0.67919(17) 0.4229(3) 0.092(2) Uani 1 1 d . . . O5 O 0.1605(5) 0.7500 0.1879(4) 0.0652(19) Uani 1 2 d S . . O6 O 0.0716(5) 0.6572(2) 0.0808(4) 0.1005(19) Uani 1 1 d U . . O7 O 0.0960(8) 0.7116(3) 0.0102(7) 0.177(4) Uani 1 1 d . . . O8 O 0.4572(5) 0.7169(3) 0.2944(7) 0.156(4) Uani 1 1 d . . . O9 O 0.3620(6) 0.6782(3) 0.0413(5) 0.133(3) Uani 1 1 d . . . O10 O 0.2032(7) 0.7500 -0.1405(5) 0.106(3) Uani 1 2 d S . . O11 O 0.9549(14) 0.6329(8) 0.3433(15) 0.196(10) Uani 0.50 1 d P . . O1W O 0.3632(3) 0.58049(14) 0.0359(3) 0.0488(11) Uani 1 1 d . . . H1WA H 0.3444 0.6040 0.0458 0.073 Uiso 1 1 calc R . . O2W O -0.0323(3) 0.54471(17) 0.1780(3) 0.0467(12) Uani 1 1 d . . . H2WA H -0.0117 0.5386 0.2216 0.070 Uiso 1 1 calc R . . O14A O -0.0022(7) 0.7500 0.0748(6) 0.029(2) Uani 1 2 d S . . O14B O -0.0009(4) 0.7320(2) 0.0865(4) 0.049(2) Uani 1 1 d . . . H1WB H 0.383(4) 0.574(2) -0.009(4) 0.046(18) Uiso 1 1 d . . . H2WB H -0.049(5) 0.529(2) 0.157(4) 0.06(3) Uiso 1 1 d . . . H3WB H -0.063(6) 0.657(3) 0.205(5) 0.09(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0245(4) 0.0440(5) 0.0290(4) -0.0037(4) 0.0011(3) 0.0026(4) Mn2 0.0407(5) 0.0405(6) 0.0424(5) -0.0021(4) -0.0045(4) 0.0042(4) C1 0.043(3) 0.040(3) 0.030(3) 0.005(2) 0.000(2) 0.001(3) C2 0.046(3) 0.038(4) 0.054(3) -0.008(3) 0.004(3) -0.003(3) C3 0.045(4) 0.035(3) 0.063(4) 0.005(3) -0.008(3) -0.005(3) C4 0.040(9) 0.34(5) 0.19(2) 0.000 -0.001(12) 0.000 C5 0.17(2) 0.101(16) 0.066(11) 0.009(10) -0.022(13) 0.028(15) C6 0.093(9) 0.098(10) 0.042(5) 0.000 0.001(6) 0.000 C7 0.067(5) 0.045(4) 0.063(4) 0.001(4) 0.008(4) 0.000(4) C8 0.031(4) 0.036(5) 0.056(5) 0.000 0.006(4) 0.000 C9 0.085(5) 0.086(5) 0.069(4) 0.003(4) 0.010(4) -0.020(4) C10 0.142(10) 0.074(7) 0.230(14) -0.062(8) 0.122(10) -0.050(7) C11 0.204(12) 0.066(6) 0.066(5) -0.027(5) -0.015(7) 0.000(7) C12 0.046(6) 0.147(10) 0.109(8) 0.000 -0.025(5) 0.000 C13 0.066(6) 0.170(10) 0.114(8) 0.000 -0.016(6) 0.000 C14 0.053(6) 0.162(10) 0.112(8) 0.000 -0.008(6) 0.000 C15 0.099(7) 0.091(8) 0.090(7) -0.026(6) 0.003(6) 0.030(6) C16 0.102(11) 0.097(11) 0.066(8) 0.000 0.019(8) 0.000 C17 0.044(4) 0.050(4) 0.061(4) 0.003(3) -0.009(3) 0.012(3) C18 0.059(5) 0.062(5) 0.087(5) -0.003(4) -0.032(4) 0.023(4) C19 0.057(4) 0.070(5) 0.060(4) -0.011(4) -0.027(3) 0.014(4) C20 0.037(3) 0.036(3) 0.041(3) 0.007(3) -0.008(3) 0.000(3) C21 0.022(3) 0.043(3) 0.037(3) 0.002(3) -0.008(2) -0.002(2) C22 0.022(3) 0.044(3) 0.030(3) 0.009(2) 0.001(2) -0.005(2) C23 0.026(3) 0.038(3) 0.030(3) 0.003(2) 0.000(2) -0.008(2) C24 0.032(3) 0.052(4) 0.034(3) -0.001(3) -0.009(2) 0.001(3) C25 0.050(4) 0.042(4) 0.040(3) -0.014(3) -0.017(3) 0.008(3) C26 0.026(3) 0.045(3) 0.044(3) -0.005(3) 0.000(2) 0.006(2) C27 0.025(3) 0.047(3) 0.028(3) -0.002(2) 0.002(2) -0.002(2) C28 0.023(3) 0.047(3) 0.024(2) 0.002(2) 0.006(2) -0.002(2) C29 0.026(3) 0.040(3) 0.034(3) 0.003(2) 0.001(2) -0.005(2) C30 0.028(3) 0.041(3) 0.031(3) 0.004(2) 0.003(2) 0.008(2) C31 0.039(3) 0.057(4) 0.059(4) -0.017(3) -0.013(3) 0.017(3) C32 0.038(3) 0.057(4) 0.047(3) -0.006(3) -0.009(3) 0.009(3) C33 0.024(3) 0.035(3) 0.036(3) -0.002(2) 0.000(2) -0.002(2) N1 0.049(3) 0.027(3) 0.059(3) 0.002(2) -0.001(2) 0.001(2) N2 0.062(5) 0.050(5) 0.056(5) 0.000 0.003(4) 0.000 N3 0.061(6) 0.121(11) 0.080(7) 0.000 -0.002(5) 0.000 N4 0.085(5) 0.099(6) 0.070(4) -0.008(4) 0.003(4) 0.015(5) N5 0.035(3) 0.040(3) 0.053(3) 0.004(2) -0.010(2) 0.004(2) N6 0.072(4) 0.074(5) 0.077(4) -0.013(4) -0.036(4) 0.023(4) N7 0.032(2) 0.047(3) 0.030(2) 0.003(2) -0.0046(19) -0.006(2) N8 0.026(2) 0.048(3) 0.036(2) 0.003(2) -0.0046(19) 0.007(2) N9 0.028(2) 0.049(3) 0.028(2) -0.005(2) -0.0030(18) 0.007(2) N10 0.030(2) 0.038(3) 0.028(2) 0.0018(19) 0.0005(18) 0.000(2) N11 0.021(2) 0.046(3) 0.032(2) -0.001(2) 0.0005(18) 0.006(2) N12 0.024(2) 0.044(3) 0.029(2) -0.008(2) -0.0022(18) 0.002(2) N13 0.023(2) 0.041(3) 0.030(2) -0.002(2) 0.0018(18) 0.0036(19) N14 0.035(3) 0.057(3) 0.045(3) -0.012(2) -0.007(2) 0.009(2) N15 0.028(2) 0.047(3) 0.038(2) -0.002(2) -0.004(2) -0.002(2) O1 0.044(2) 0.047(3) 0.051(2) -0.003(2) -0.015(2) -0.003(2) O2 0.046(2) 0.047(3) 0.045(2) -0.0076(19) 0.0081(19) 0.008(2) O3W 0.054(4) 0.084(5) 0.159(7) -0.061(5) 0.018(4) 0.015(3) O3 0.32(2) 0.155(12) 0.35(2) 0.006(13) 0.136(17) -0.037(12) O4 0.153(6) 0.050(3) 0.074(4) 0.024(3) 0.007(4) -0.003(4) O5 0.093(5) 0.056(4) 0.047(4) 0.000 0.015(4) 0.000 O6 0.126(5) 0.085(4) 0.090(4) 0.026(3) -0.018(4) -0.038(4) O7 0.225(11) 0.096(7) 0.210(10) 0.033(7) 0.073(9) 0.033(7) O8 0.108(6) 0.101(6) 0.258(11) 0.035(7) -0.068(7) 0.018(5) O9 0.161(8) 0.114(7) 0.124(6) -0.037(5) -0.037(5) 0.057(6) O10 0.151(9) 0.115(8) 0.051(5) 0.000 -0.001(5) 0.000 O11 0.163(19) 0.20(2) 0.23(2) 0.016(19) 0.048(17) -0.040(16) O1W 0.058(3) 0.050(3) 0.039(2) 0.000(2) 0.020(2) 0.008(2) O2W 0.057(3) 0.050(3) 0.033(2) 0.005(2) -0.010(2) -0.005(2) O14A 0.046(5) 0.020(7) 0.022(4) 0.000 0.005(3) 0.000 O14B 0.042(3) 0.049(6) 0.054(3) 0.012(3) 0.024(2) 0.027(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 O2 2.155(4) . ? Mn1 O1W 2.213(4) . ? Mn1 N11 2.277(4) . ? Mn1 N9 2.293(4) . ? Mn1 N10 2.309(4) . ? Mn1 N15 2.318(5) 6_556 ? Mn2 O6 2.113(6) . ? Mn2 O3W 2.157(6) . ? Mn2 O1 2.152(4) . ? Mn2 O2W 2.184(5) . ? Mn2 N8 2.193(5) . ? Mn2 N5 2.393(5) . ? C1 O1 1.248(7) . ? C1 O2 1.266(7) . ? C1 C2 1.523(8) . ? C2 C3 1.508(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.479(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O3 1.270(19) 7_575 ? C4 O3 1.270(19) . ? C4 C5 1.480(16) . ? C4 C5 1.480(16) 7_575 ? C5 C5 1.53(4) 7_575 ? C5 C6 1.581(15) . ? C5 H5 0.9800 . ? C6 N2 1.462(12) . ? C6 C5 1.581(15) 7_575 ? C6 H6 0.9800 . ? C7 O4 1.187(8) . ? C7 N2 1.394(8) . ? C7 N1 1.398(8) . ? C8 O5 1.208(10) . ? C8 N1 1.377(7) 7_575 ? C8 N1 1.377(7) . ? C9 O6 1.095(9) . ? C9 O7 1.336(12) . ? C9 C10 1.455(13) . ? C10 C11 1.622(15) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N4 1.531(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O8 1.242(10) . ? C12 O8 1.242(10) 7_575 ? C12 C13 1.420(18) . ? C13 C14 1.468(14) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N3 1.529(16) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 O9 1.224(12) . ? C15 N4 1.371(12) . ? C15 N3 1.389(12) . ? C16 O10 1.205(16) . ? C16 N4 1.397(10) . ? C16 N4 1.397(10) 7_575 ? C17 N5 1.325(7) . ? C17 C18 1.380(9) . ? C17 H17 0.9300 . ? C18 N6 1.305(10) . ? C18 H18 0.9300 . ? C19 N6 1.351(9) . ? C19 C20 1.395(8) . ? C19 H19 0.9300 . ? C20 N5 1.348(8) . ? C20 C21 1.465(7) . ? C21 N8 1.341(7) . ? C21 N7 1.360(7) . ? C22 N9 1.344(7) . ? C22 N7 1.351(6) . ? C22 C23 1.458(8) . ? C23 N10 1.360(6) . ? C23 C24 1.381(8) . ? C24 C25 1.391(8) . ? C24 H24 0.9300 . ? C25 C26 1.389(8) . ? C25 H25 0.9300 . ? C26 C27 1.373(8) . ? C26 H26 0.9300 . ? C27 N10 1.349(7) . ? C27 C28 1.469(7) . ? C28 N11 1.345(7) . ? C28 N13 1.345(7) . ? C29 N12 1.340(7) . ? C29 N13 1.361(7) . ? C29 C30 1.488(7) . ? C30 N14 1.342(7) . ? C30 C33 1.384(7) . ? C31 N14 1.335(7) . ? C31 C32 1.368(9) . ? C31 H31 0.9300 . ? C32 N15 1.353(8) . ? C32 H32 0.9300 . ? C33 N15 1.346(7) . ? C33 H33 0.9300 . ? N2 C7 1.394(8) 7_575 ? N3 C15 1.389(11) 7_575 ? N8 N9 1.370(6) . ? N11 N12 1.371(6) . ? N15 Mn1 2.318(5) 6_656 ? O3W H3WA 0.8200 . ? O3W H3WB 0.78(10) . ? O1W H1WA 0.8200 . ? O1W H1WB 0.84(6) . ? O2W H2WA 0.8200 . ? O2W H2WB 0.67(7) . ? O14A O14B 0.607(5) 7_575 ? O14A O14B 0.607(5) . ? O14B O14B 1.148(13) 7_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O1W 83.87(17) . . ? O2 Mn1 N11 110.76(16) . . ? O1W Mn1 N11 90.02(17) . . ? O2 Mn1 N9 108.46(16) . . ? O1W Mn1 N9 92.13(17) . . ? N11 Mn1 N9 140.72(16) . . ? O2 Mn1 N10 171.59(16) . . ? O1W Mn1 N10 87.93(16) . . ? N11 Mn1 N10 70.96(15) . . ? N9 Mn1 N10 69.93(15) . . ? O2 Mn1 N15 93.08(17) . 6_556 ? O1W Mn1 N15 173.73(17) . 6_556 ? N11 Mn1 N15 85.95(16) . 6_556 ? N9 Mn1 N15 94.03(16) . 6_556 ? N10 Mn1 N15 95.26(16) . 6_556 ? O6 Mn2 O3W 83.7(3) . . ? O6 Mn2 O1 95.0(2) . . ? O3W Mn2 O1 104.0(2) . . ? O6 Mn2 O2W 162.7(3) . . ? O3W Mn2 O2W 81.9(3) . . ? O1 Mn2 O2W 97.82(17) . . ? O6 Mn2 N8 103.0(3) . . ? O3W Mn2 N8 166.9(2) . . ? O1 Mn2 N8 86.86(16) . . ? O2W Mn2 N8 89.41(19) . . ? O6 Mn2 N5 84.3(2) . . ? O3W Mn2 N5 98.0(3) . . ? O1 Mn2 N5 157.81(17) . . ? O2W Mn2 N5 88.22(18) . . ? N8 Mn2 N5 71.81(16) . . ? O1 C1 O2 124.8(6) . . ? O1 C1 C2 118.2(5) . . ? O2 C1 C2 117.0(5) . . ? C3 C2 C1 114.5(5) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N1 C3 C2 112.5(5) . . ? N1 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N1 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? O3 C4 O3 95(2) 7_575 . ? O3 C4 C5 149(2) 7_575 . ? O3 C4 C5 95.6(11) . . ? O3 C4 C5 95.6(11) 7_575 7_575 ? O3 C4 C5 149(2) . 7_575 ? C5 C4 C5 62.1(15) . 7_575 ? C4 C5 C5 58.9(8) . 7_575 ? C4 C5 C6 112.1(13) . . ? C5 C5 C6 61.1(7) 7_575 . ? C4 C5 H5 116.5 . . ? C5 C5 H5 116.5 7_575 . ? C6 C5 H5 116.5 . . ? N2 C6 C5 107.7(10) . 7_575 ? N2 C6 C5 107.7(10) . . ? C5 C6 C5 57.8(15) 7_575 . ? N2 C6 H6 122.2 . . ? C5 C6 H6 122.2 7_575 . ? C5 C6 H6 122.2 . . ? O4 C7 N2 122.0(7) . . ? O4 C7 N1 123.2(7) . . ? N2 C7 N1 114.8(6) . . ? O5 C8 N1 122.4(4) . 7_575 ? O5 C8 N1 122.4(4) . . ? N1 C8 N1 115.1(8) 7_575 . ? O6 C9 O7 122.0(11) . . ? O6 C9 C10 117.4(11) . . ? O7 C9 C10 119.2(9) . . ? C9 C10 C11 114.1(11) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? N4 C11 C10 112.9(7) . . ? N4 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? N4 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? O8 C12 O8 116.1(15) . 7_575 ? O8 C12 C13 121.5(7) . . ? O8 C12 C13 121.5(7) 7_575 . ? C12 C13 C14 120.0(12) . . ? C12 C13 H13A 107.3 . . ? C14 C13 H13A 107.3 . . ? C12 C13 H13B 107.3 . . ? C14 C13 H13B 107.3 . . ? H13A C13 H13B 106.9 . . ? C13 C14 N3 112.2(11) . . ? C13 C14 H14A 109.2 . . ? N3 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? N3 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? O9 C15 N4 121.4(10) . . ? O9 C15 N3 122.0(10) . . ? N4 C15 N3 116.5(10) . . ? O10 C16 N4 121.1(7) . . ? O10 C16 N4 121.1(7) . 7_575 ? N4 C16 N4 117.8(13) . 7_575 ? N5 C17 C18 120.0(7) . . ? N5 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? N6 C18 C17 124.8(7) . . ? N6 C18 H18 117.6 . . ? C17 C18 H18 117.6 . . ? N6 C19 C20 122.1(7) . . ? N6 C19 H19 119.0 . . ? C20 C19 H19 119.0 . . ? N5 C20 C19 120.0(5) . . ? N5 C20 C21 116.5(5) . . ? C19 C20 C21 123.4(6) . . ? N8 C21 N7 113.7(4) . . ? N8 C21 C20 117.8(5) . . ? N7 C21 C20 128.5(5) . . ? N9 C22 N7 113.7(5) . . ? N9 C22 C23 118.6(4) . . ? N7 C22 C23 127.6(5) . . ? N10 C23 C24 120.5(5) . . ? N10 C23 C22 113.0(5) . . ? C24 C23 C22 126.5(5) . . ? C23 C24 C25 118.8(5) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C26 C25 C24 120.1(5) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C25 118.8(5) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? N10 C27 C26 121.2(5) . . ? N10 C27 C28 112.8(5) . . ? C26 C27 C28 126.0(5) . . ? N11 C28 N13 114.1(4) . . ? N11 C28 C27 119.8(5) . . ? N13 C28 C27 126.1(5) . . ? N12 C29 N13 114.3(5) . . ? N12 C29 C30 121.9(5) . . ? N13 C29 C30 123.7(5) . . ? N14 C30 C33 122.5(5) . . ? N14 C30 C29 117.2(5) . . ? C33 C30 C29 120.3(5) . . ? N14 C31 C32 124.0(6) . . ? N14 C31 H31 118.0 . . ? C32 C31 H31 118.0 . . ? N15 C32 C31 121.1(5) . . ? N15 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? N15 C33 C30 121.7(5) . . ? N15 C33 H33 119.1 . . ? C30 C33 H33 119.1 . . ? C8 N1 C7 125.3(6) . . ? C8 N1 C3 118.0(5) . . ? C7 N1 C3 116.6(5) . . ? C7 N2 C7 124.2(8) . 7_575 ? C7 N2 C6 117.7(4) . . ? C7 N2 C6 117.7(4) 7_575 . ? C15 N3 C15 124.2(12) . 7_575 ? C15 N3 C14 117.8(6) . . ? C15 N3 C14 117.8(6) 7_575 . ? C15 N4 C16 122.2(10) . . ? C15 N4 C11 120.0(9) . . ? C16 N4 C11 117.4(9) . . ? C17 N5 C20 118.0(5) . . ? C17 N5 Mn2 128.1(4) . . ? C20 N5 Mn2 113.6(3) . . ? C18 N6 C19 115.2(6) . . ? C22 N7 C21 101.2(4) . . ? C21 N8 N9 105.6(4) . . ? C21 N8 Mn2 119.9(3) . . ? N9 N8 Mn2 134.2(3) . . ? C22 N9 N8 105.8(4) . . ? C22 N9 Mn1 117.8(3) . . ? N8 N9 Mn1 134.9(3) . . ? C27 N10 C23 120.6(4) . . ? C27 N10 Mn1 119.5(3) . . ? C23 N10 Mn1 119.9(3) . . ? C28 N11 N12 105.8(4) . . ? C28 N11 Mn1 116.9(3) . . ? N12 N11 Mn1 137.2(3) . . ? C29 N12 N11 105.0(4) . . ? C28 N13 C29 100.8(4) . . ? C31 N14 C30 114.8(5) . . ? C33 N15 C32 115.8(5) . . ? C33 N15 Mn1 119.5(4) . 6_656 ? C32 N15 Mn1 124.7(4) . 6_656 ? C1 O1 Mn2 144.0(4) . . ? C1 O2 Mn1 122.8(4) . . ? Mn2 O3W H3WA 109.5 . . ? Mn2 O3W H3WB 136(7) . . ? H3WA O3W H3WB 111.9 . . ? C9 O6 Mn2 140.4(8) . . ? Mn1 O1W H1WA 109.5 . . ? Mn1 O1W H1WB 124(4) . . ? H1WA O1W H1WB 122.4 . . ? Mn2 O2W H2WA 109.5 . . ? Mn2 O2W H2WB 125(7) . . ? H2WA O2W H2WB 116.0 . . ? O14B O14A O14B 142(3) 7_575 . ? O14A O14B O14B 18.9(15) . 7_575 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.977 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 907894' ####################################################################### # # 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_p-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H52 Mn3 N10 O22' _chemical_formula_weight 1225.77 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 13.519(3) _cell_length_b 14.955(3) _cell_length_c 15.356(3) _cell_angle_alpha 102.35(3) _cell_angle_beta 109.47(3) _cell_angle_gamma 110.99(3) _cell_volume 2529.3(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9052 _cell_measurement_theta_min 1.7260 _cell_measurement_theta_max 29.1511 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1262 _exptl_absorpt_coefficient_mu 0.830 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8323 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 ; Saturn724 (4x4 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21412 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8864 _reflns_number_gt 8073 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+1.6684P] 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 8864 _refine_ls_number_parameters 715 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.130 _refine_ls_shift/su_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O17 O 0.27295(6) 1.11601(5) 0.57713(5) 0.0381(2) Uani 1 1 d . . . O16 O 0.99538(6) 1.06175(6) 0.75880(6) 0.0425(3) Uani 1 1 d . . . O15 O 0.90159(6) 0.92025(5) 0.62739(5) 0.0356(2) Uani 1 1 d . . . O1W O -0.31679(7) 0.66538(6) 0.34143(6) 0.0527(3) Uani 1 1 d . . . H1WA H -0.3072 0.6146 0.3434 0.079 Uiso 1 1 calc R . . C23 C 0.90114(8) 0.99338(7) 0.68689(7) 0.0270(3) Uani 1 1 d . . . C24 C 0.78504(8) 0.99166(9) 0.67328(8) 0.0383(4) Uani 1 1 d . . . H24A H 0.7311 0.9247 0.6678 0.046 Uiso 1 1 calc R . . H24B H 0.7501 1.0006 0.6115 0.046 Uiso 1 1 calc R . . O21 O 0.93112(6) 0.18155(5) 1.35598(6) 0.0369(2) Uani 1 1 d . . . O20 O 1.12179(6) 0.29631(5) 1.45089(5) 0.0359(2) Uani 1 1 d . . . C22 C 1.01709(8) 0.27162(7) 1.39618(7) 0.0279(3) Uani 1 1 d . . . O7 O 1.48839(6) 0.63788(6) 1.17993(5) 0.0407(3) Uani 1 1 d . . . O6 O 1.32465(6) 0.60309(6) 1.05702(5) 0.0424(3) Uani 1 1 d . . . C11 C 1.38214(8) 0.62229(7) 1.14716(7) 0.0286(3) Uani 1 1 d . . . C33 C -0.11406(8) 0.83245(8) 0.97780(7) 0.0316(3) Uani 1 1 d . . . H33A H -0.1399 0.8851 0.9773 0.038 Uiso 1 1 calc R . . H33B H -0.0717 0.8424 1.0468 0.038 Uiso 1 1 calc R . . O5 O 1.20369(6) 0.46440(6) 1.30766(6) 0.0502(3) Uani 1 1 d . . . Mn1 Mn 0.476920(11) 0.605313(10) 1.027155(10) 0.02468(4) Uani 1 1 d . . . Mn2 Mn -0.206719(12) 0.788669(10) 0.485258(10) 0.02522(4) Uani 1 1 d . . . Mn3 Mn 0.088006(12) 0.962047(11) 0.724994(11) 0.02585(4) Uani 1 1 d . . . O13 O 0.14326(6) 1.02308(5) 0.62145(5) 0.0348(2) Uani 1 1 d . . . N3 N 1.08122(6) 0.51648(6) 1.34867(6) 0.0265(2) Uani 1 1 d . . . O4 O 0.94751(6) 0.55882(6) 1.37753(5) 0.0403(2) Uani 1 1 d . . . O11 O 0.61610(6) 1.11931(6) 0.68189(6) 0.0472(3) Uani 1 1 d . . . O2W O -0.05891(6) 0.84558(6) 0.44242(6) 0.0411(3) Uani 1 1 d . . . H2WA H -0.0735 0.8757 0.4049 0.062 Uiso 1 1 calc R . . O9 O 0.54109(7) 0.76772(5) 1.02196(5) 0.0428(3) Uani 1 1 d . . . O1 O 0.61635(5) 0.56202(5) 1.05479(5) 0.0316(2) Uani 1 1 d . . . N2 N 1.00400(6) 0.60721(6) 1.26346(6) 0.0274(2) Uani 1 1 d . . . N5 N 0.59848(7) 0.97010(6) 0.86586(6) 0.0292(3) Uani 1 1 d . . . O12 O 0.43703(6) 0.98761(6) 0.86050(5) 0.0436(2) Uani 1 1 d . . . N4 N 0.69572(6) 1.04529(6) 0.77972(6) 0.0276(2) Uani 1 1 d . . . O8 O 0.42260(7) 0.63424(6) 0.88442(6) 0.0427(3) Uani 1 1 d . . . C6 C 1.00652(8) 0.56086(7) 1.33258(7) 0.0269(3) Uani 1 1 d . . . N8 N -0.03285(7) 0.84621(6) 0.93226(6) 0.0285(3) Uani 1 1 d . . . C7 C 1.08533(8) 0.46396(7) 1.42075(7) 0.0287(3) Uani 1 1 d . . . H7A H 1.0790 0.5024 1.4764 0.034 Uiso 1 1 calc R . . H7B H 1.1610 0.4634 1.4467 0.034 Uiso 1 1 calc R . . N1 N 1.13445(7) 0.55514(6) 1.22626(6) 0.0314(3) Uani 1 1 d . . . O3 O 1.06181(7) 0.64700(6) 1.14865(6) 0.0523(3) Uani 1 1 d . . . C5 C 1.14401(8) 0.50866(8) 1.29532(8) 0.0317(3) Uani 1 1 d . . . N6 N 0.52591(6) 1.05703(6) 0.77273(6) 0.0287(2) Uani 1 1 d . . . N7 N 0.05714(7) 0.90030(6) 0.84084(6) 0.0330(3) Uani 1 1 d . . . C21 C 0.23950(8) 1.05204(7) 0.61466(7) 0.0272(3) Uani 1 1 d . . . C35 C -0.28322(9) 0.69397(8) 0.81204(7) 0.0315(3) Uani 1 1 d . . . H35A H -0.2904 0.7516 0.7965 0.038 Uiso 1 1 calc R . . H35B H -0.2342 0.6774 0.7845 0.038 Uiso 1 1 calc R . . N9 N -0.43650(7) 0.62015(6) 0.59952(6) 0.0301(3) Uani 1 1 d . . . C16 C 0.61240(8) 1.07672(7) 0.74024(7) 0.0291(3) Uani 1 1 d . . . O10 O 0.76246(6) 0.95891(6) 0.86883(6) 0.0471(3) Uani 1 1 d . . . O3W O 0.23944(7) 1.09846(6) 0.83885(7) 0.0515(3) Uani 1 1 d . . . H3WA H 0.2268 1.1483 0.8399 0.077 Uiso 1 1 calc R . . C9 C 1.19643(8) 0.54556(9) 1.16443(7) 0.0354(3) Uani 1 1 d . . . H9A H 1.1566 0.5520 1.1024 0.043 Uiso 1 1 calc R . . H9B H 1.1918 0.4774 1.1482 0.043 Uiso 1 1 calc R . . C12 C 0.48693(8) 0.73048(7) 0.92938(7) 0.0283(3) Uani 1 1 d . . . C34 C -0.22198(9) 0.72689(8) 0.92478(7) 0.0333(3) Uani 1 1 d . . . H34A H -0.2784 0.7273 0.9505 0.040 Uiso 1 1 calc R . . H34B H -0.1981 0.6760 0.9401 0.040 Uiso 1 1 calc R . . C15 C 0.69035(8) 0.98908(7) 0.84030(7) 0.0290(3) Uani 1 1 d . . . N10 N -0.34820(7) 0.72223(6) 0.53272(6) 0.0319(3) Uani 1 1 d . . . C1 C 0.72455(8) 0.62656(7) 1.12122(7) 0.0281(3) Uani 1 1 d . . . C28 C 0.04720(8) 0.80764(8) 0.94044(7) 0.0291(3) Uani 1 1 d . . . C19 C 0.43802(8) 1.09390(7) 0.73741(8) 0.0328(3) Uani 1 1 d . . . H19A H 0.4693 1.1483 0.7144 0.039 Uiso 1 1 calc R . . H19B H 0.4245 1.1230 0.7925 0.039 Uiso 1 1 calc R . . C27 C 0.10376(8) 0.84287(8) 0.88423(7) 0.0315(3) Uani 1 1 d . . . C3 C 0.92477(8) 0.65578(7) 1.24204(8) 0.0296(3) Uani 1 1 d . . . H3A H 0.9642 0.7190 1.2330 0.036 Uiso 1 1 calc R . . H3B H 0.9079 0.6736 1.2981 0.036 Uiso 1 1 calc R . . C2 C 0.80941(8) 0.58216(7) 1.14849(8) 0.0305(3) Uani 1 1 d . . . H2A H 0.8274 0.5637 1.0932 0.037 Uiso 1 1 calc R . . H2B H 0.7708 0.5193 1.1583 0.037 Uiso 1 1 calc R . . C26 C -0.02242(9) 0.89992(7) 0.87189(7) 0.0311(3) Uani 1 1 d . . . H26 H -0.0676 0.9334 0.8542 0.037 Uiso 1 1 calc R . . C40 C -0.50347(8) 0.66961(8) 0.57076(7) 0.0298(3) Uani 1 1 d . . . C4 C 1.06661(8) 0.60648(8) 1.20889(7) 0.0306(3) Uani 1 1 d . . . C17 C 0.51524(8) 1.00479(7) 0.83557(7) 0.0299(3) Uani 1 1 d . . . C37 C -0.45323(9) 0.54768(7) 0.65069(7) 0.0324(3) Uani 1 1 d . . . H37A H -0.4139 0.5068 0.6387 0.039 Uiso 1 1 calc R . . H37B H -0.5372 0.5008 0.6226 0.039 Uiso 1 1 calc R . . C18 C 0.79909(8) 1.07575(8) 0.75898(8) 0.0330(3) Uani 1 1 d . . . H18A H 0.8689 1.0933 0.8186 0.040 Uiso 1 1 calc R . . H18B H 0.8118 1.1372 0.7433 0.040 Uiso 1 1 calc R . . C39 C -0.44848(8) 0.73246(8) 0.52747(7) 0.0312(3) Uani 1 1 d . . . C20 C 0.32206(9) 1.00792(8) 0.65383(8) 0.0364(3) Uani 1 1 d . . . H20A H 0.2863 0.9563 0.6780 0.044 Uiso 1 1 calc R . . H20B H 0.3357 0.9748 0.6006 0.044 Uiso 1 1 calc R . . O2 O 0.75747(7) 0.71854(6) 1.15900(8) 0.0606(4) Uani 1 1 d . . . C38 C -0.34634(8) 0.65511(8) 0.57582(7) 0.0317(3) Uani 1 1 d . . . H38 H -0.2880 0.6338 0.5887 0.038 Uiso 1 1 calc R . . C14 C 0.58721(9) 0.91016(8) 0.93071(7) 0.0344(3) Uani 1 1 d . . . H14A H 0.5643 0.9402 0.9783 0.041 Uiso 1 1 calc R . . H14B H 0.6633 0.9138 0.9678 0.041 Uiso 1 1 calc R . . C13 C 0.49563(10) 0.79841(8) 0.86911(8) 0.0368(4) Uani 1 1 d . . . H13A H 0.5151 0.7711 0.8175 0.044 Uiso 1 1 calc R . . H13B H 0.4188 0.7953 0.8364 0.044 Uiso 1 1 calc R . . C36 C -0.40489(9) 0.60165(8) 0.76271(7) 0.0324(3) Uani 1 1 d . . . H36A H -0.4597 0.6241 0.7749 0.039 Uiso 1 1 calc R . . H36B H -0.4017 0.5520 0.7938 0.039 Uiso 1 1 calc R . . C41 C -0.49532(9) 0.79193(8) 0.48850(8) 0.0389(4) Uani 1 1 d . . . H41 H -0.4605 0.8327 0.4585 0.047 Uiso 1 1 calc R . . C10 C 1.32470(8) 0.62623(9) 1.21606(8) 0.0359(3) Uani 1 1 d . . . H10A H 1.3669 0.6150 1.2740 0.043 Uiso 1 1 calc R . . H10B H 1.3301 0.6943 1.2389 0.043 Uiso 1 1 calc R . . C32 C 0.07401(10) 0.74694(8) 0.99153(8) 0.0413(4) Uani 1 1 d . . . H32 H 0.0339 0.7225 1.0270 0.050 Uiso 1 1 calc R . . C44 C -0.60370(9) 0.66544(9) 0.57886(8) 0.0412(4) Uani 1 1 d . . . H44 H -0.6392 0.6241 0.6081 0.049 Uiso 1 1 calc R . . C42 C -0.59531(10) 0.78821(9) 0.49595(9) 0.0484(4) Uani 1 1 d . . . H42 H -0.6285 0.8274 0.4708 0.058 Uiso 1 1 calc R . . C29 C 0.19503(9) 0.82152(9) 0.88186(9) 0.0455(4) Uani 1 1 d . . . H29 H 0.2359 0.8463 0.8470 0.055 Uiso 1 1 calc R . . C31 C 0.16240(11) 0.72481(10) 0.98711(10) 0.0593(4) Uani 1 1 d . . . H31 H 0.1831 0.6843 1.0203 0.071 Uiso 1 1 calc R . . C43 C -0.64810(10) 0.72631(10) 0.54087(9) 0.0501(4) Uani 1 1 d . . . H43 H -0.7151 0.7262 0.5452 0.060 Uiso 1 1 calc R . . C8 C 0.98578(10) 0.35358(8) 1.37249(10) 0.0434(4) Uani 1 1 d . . . H8A H 0.9242 0.3526 1.3918 0.052 Uiso 1 1 calc R . . H8B H 0.9521 0.3343 1.3007 0.052 Uiso 1 1 calc R . . C30 C 0.22222(10) 0.76199(10) 0.93357(10) 0.0609(4) Uani 1 1 d . . . H30 H 0.2824 0.7460 0.9328 0.073 Uiso 1 1 calc R . . O22 O 0.70577(7) 0.48989(6) 0.31375(6) 0.0475(3) Uani 1 1 d . . . H3WB H 0.3061(11) 1.1142(9) 0.8830(9) 0.057 Uiso 1 1 d . . . H1WB H -0.3780(11) 0.6661(9) 0.3009(9) 0.057 Uiso 1 1 d . . . H2WB H 0.0079(10) 0.8943(9) 0.5036(9) 0.057 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 O17 0.0340(3) 0.0481(3) 0.0576(3) 0.0405(2) 0.0281(2) 0.0260(2) O16 0.0233(3) 0.0452(4) 0.0450(4) 0.0015(3) 0.0108(3) 0.0151(3) O15 0.0278(3) 0.0380(3) 0.0361(3) 0.0051(3) 0.0119(2) 0.0180(2) O1W 0.0530(4) 0.0481(4) 0.0358(4) 0.0070(3) 0.0001(4) 0.0257(3) C23 0.0232(3) 0.0333(4) 0.0296(4) 0.0156(3) 0.0129(3) 0.0155(3) C24 0.0263(4) 0.0477(5) 0.0364(5) 0.0073(4) 0.0122(4) 0.0193(4) O21 0.0357(3) 0.0261(3) 0.0505(4) 0.0158(3) 0.0211(3) 0.0138(2) O20 0.0308(3) 0.0367(3) 0.0488(3) 0.0258(3) 0.0161(3) 0.0205(2) C22 0.0322(4) 0.0304(4) 0.0325(4) 0.0182(3) 0.0204(3) 0.0171(3) O7 0.0280(3) 0.0649(4) 0.0337(3) 0.0205(3) 0.0147(2) 0.0242(3) O6 0.0362(3) 0.0708(4) 0.0330(3) 0.0230(3) 0.0196(2) 0.0322(3) C11 0.0302(4) 0.0292(4) 0.0318(4) 0.0134(3) 0.0166(3) 0.0160(3) C33 0.0356(4) 0.0371(4) 0.0292(4) 0.0162(3) 0.0164(3) 0.0202(3) O5 0.0644(3) 0.0699(3) 0.0702(4) 0.0473(3) 0.0470(3) 0.0581(2) Mn1 0.02492(5) 0.02944(6) 0.02945(6) 0.01624(5) 0.01544(4) 0.01661(4) Mn2 0.02373(5) 0.02807(6) 0.02788(6) 0.01554(5) 0.01172(5) 0.01319(5) Mn3 0.02160(5) 0.02705(6) 0.03076(6) 0.01485(5) 0.01177(5) 0.01099(5) O13 0.0278(3) 0.0430(3) 0.0466(3) 0.0298(2) 0.0206(2) 0.0187(2) N3 0.0276(3) 0.0314(3) 0.0316(3) 0.0191(3) 0.0162(3) 0.0183(2) O4 0.0424(3) 0.0661(3) 0.0467(3) 0.0370(3) 0.0334(2) 0.0387(2) O11 0.0529(3) 0.0661(3) 0.0657(3) 0.0530(3) 0.0414(3) 0.0418(3) O2W 0.0406(3) 0.0521(3) 0.0476(3) 0.0290(3) 0.0259(3) 0.0273(3) O9 0.0426(4) 0.0354(3) 0.0343(3) 0.0192(3) 0.0059(3) 0.0092(3) O1 0.0210(3) 0.0332(3) 0.0399(3) 0.0148(3) 0.0108(2) 0.0140(2) N2 0.0247(3) 0.0360(3) 0.0325(3) 0.0214(3) 0.0139(3) 0.0192(3) N5 0.0301(3) 0.0320(3) 0.0363(3) 0.0229(3) 0.0158(3) 0.0187(3) O12 0.0423(3) 0.0629(4) 0.0554(3) 0.0382(3) 0.0358(2) 0.0328(3) N4 0.0234(3) 0.0327(3) 0.0378(4) 0.0189(3) 0.0173(3) 0.0179(2) O8 0.0534(4) 0.0305(3) 0.0378(3) 0.0143(3) 0.0216(3) 0.0114(3) C6 0.0230(4) 0.0295(4) 0.0305(4) 0.0149(3) 0.0114(3) 0.0130(3) N8 0.0297(3) 0.0320(3) 0.0305(3) 0.0168(3) 0.0152(3) 0.0168(3) C7 0.0317(4) 0.0287(4) 0.0321(4) 0.0197(3) 0.0132(3) 0.0171(3) N1 0.0302(3) 0.0445(4) 0.0367(3) 0.0235(3) 0.0226(3) 0.0231(3) O3 0.0584(3) 0.0830(4) 0.0641(3) 0.0588(3) 0.0441(3) 0.0489(3) C5 0.0321(4) 0.0356(4) 0.0359(4) 0.0169(3) 0.0185(3) 0.0195(3) N6 0.0264(3) 0.0368(3) 0.0396(3) 0.0254(3) 0.0188(3) 0.0217(2) N7 0.0364(3) 0.0359(4) 0.0353(4) 0.0215(3) 0.0186(3) 0.0189(3) C21 0.0239(4) 0.0301(4) 0.0318(4) 0.0167(3) 0.0126(3) 0.0139(3) C35 0.0328(4) 0.0331(4) 0.0312(4) 0.0146(3) 0.0168(3) 0.0144(3) N9 0.0266(3) 0.0318(4) 0.0299(3) 0.0154(3) 0.0122(3) 0.0098(3) C16 0.0275(4) 0.0335(4) 0.0386(4) 0.0208(3) 0.0191(3) 0.0188(3) O10 0.0452(3) 0.0611(3) 0.0609(4) 0.0382(3) 0.0252(3) 0.0411(2) O3W 0.0332(4) 0.0322(3) 0.0589(5) 0.0097(3) -0.0027(4) 0.0107(3) C9 0.0349(4) 0.0469(5) 0.0360(4) 0.0180(4) 0.0245(3) 0.0214(4) C12 0.0268(4) 0.0300(4) 0.0346(4) 0.0166(3) 0.0164(3) 0.0149(3) C34 0.0327(4) 0.0407(5) 0.0316(4) 0.0184(4) 0.0171(3) 0.0171(4) C15 0.0280(4) 0.0294(4) 0.0337(4) 0.0146(3) 0.0126(3) 0.0170(3) N10 0.0255(3) 0.0371(4) 0.0360(4) 0.0195(3) 0.0158(3) 0.0126(3) C1 0.0249(4) 0.0314(4) 0.0331(4) 0.0174(3) 0.0134(3) 0.0147(3) C28 0.0264(4) 0.0342(4) 0.0276(4) 0.0130(3) 0.0108(3) 0.0155(3) C19 0.0285(4) 0.0389(4) 0.0478(5) 0.0257(4) 0.0200(3) 0.0246(3) C27 0.0275(4) 0.0368(4) 0.0310(4) 0.0166(3) 0.0111(3) 0.0158(3) C3 0.0249(4) 0.0353(4) 0.0361(4) 0.0184(3) 0.0130(3) 0.0194(3) C2 0.0226(4) 0.0311(4) 0.0376(5) 0.0144(4) 0.0109(3) 0.0139(3) C26 0.0330(4) 0.0309(4) 0.0360(4) 0.0190(3) 0.0157(3) 0.0175(3) C40 0.0248(4) 0.0319(4) 0.0261(4) 0.0116(3) 0.0079(3) 0.0095(3) C4 0.0248(4) 0.0396(4) 0.0376(4) 0.0225(3) 0.0178(3) 0.0175(3) C17 0.0312(4) 0.0320(4) 0.0334(4) 0.0165(3) 0.0166(3) 0.0173(3) C37 0.0300(4) 0.0288(4) 0.0363(4) 0.0168(3) 0.0147(3) 0.0091(4) C18 0.0248(3) 0.0355(4) 0.0450(5) 0.0155(4) 0.0211(3) 0.0153(3) C39 0.0240(4) 0.0335(5) 0.0297(4) 0.0111(4) 0.0106(3) 0.0088(3) C20 0.0327(4) 0.0343(4) 0.0513(5) 0.0261(4) 0.0178(4) 0.0201(3) O2 0.0413(4) 0.0322(3) 0.0801(6) 0.0105(4) 0.0006(4) 0.0195(3) C38 0.0255(4) 0.0353(5) 0.0335(4) 0.0144(4) 0.0147(3) 0.0113(3) C14 0.0386(4) 0.0368(4) 0.0347(4) 0.0236(3) 0.0157(4) 0.0194(3) C13 0.0443(5) 0.0350(4) 0.0350(4) 0.0201(4) 0.0177(4) 0.0185(4) C36 0.0336(4) 0.0373(4) 0.0345(4) 0.0197(3) 0.0193(3) 0.0176(3) C41 0.0338(5) 0.0460(5) 0.0376(5) 0.0244(4) 0.0137(4) 0.0164(4) C10 0.0343(4) 0.0418(5) 0.0339(4) 0.0109(4) 0.0209(3) 0.0168(4) C32 0.0486(5) 0.0530(5) 0.0429(5) 0.0319(4) 0.0251(4) 0.0325(4) C44 0.0342(4) 0.0517(5) 0.0456(5) 0.0266(4) 0.0231(4) 0.0184(4) C42 0.0408(5) 0.0619(5) 0.0573(6) 0.0363(4) 0.0221(4) 0.0309(4) C29 0.0404(4) 0.0652(6) 0.0484(5) 0.0310(4) 0.0269(4) 0.0305(4) C31 0.0693(5) 0.0861(6) 0.0668(6) 0.0538(5) 0.0376(5) 0.0602(4) C43 0.0388(4) 0.0689(6) 0.0628(6) 0.0366(5) 0.0295(4) 0.0325(4) C8 0.0302(5) 0.0325(4) 0.0592(6) 0.0253(4) 0.0074(5) 0.0136(4) C30 0.0573(5) 0.0977(6) 0.0717(7) 0.0514(5) 0.0378(5) 0.0612(4) O22 0.0408(3) 0.0517(4) 0.0492(4) 0.0176(3) 0.0248(3) 0.0172(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 O17 C21 1.2457(14) . ? O17 Mn2 2.1629(10) 2_576 ? O16 C23 1.2384(13) . ? O16 Mn3 2.3455(11) 1_655 ? O15 C23 1.2698(14) . ? O15 Mn2 2.1789(16) 1_655 ? O15 Mn3 2.2227(12) 1_655 ? O1W Mn2 2.1432(16) . ? O1W H1WA 0.8200 . ? O1W H1WB 0.860(14) . ? C23 C24 1.5026(17) . ? C23 Mn3 2.6313(13) 1_655 ? C24 C18 1.5179(18) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? O21 C22 1.2612(13) . ? O21 Mn3 2.1144(11) 2_667 ? O20 C22 1.2432(13) . ? O20 Mn2 2.1731(10) 2_667 ? C22 C8 1.5078(18) . ? O7 C11 1.2643(14) . ? O7 Mn1 2.2316(10) 1_655 ? O6 C11 1.2472(13) . ? O6 Mn1 2.2440(10) 1_655 ? C11 C10 1.5100(18) . ? C11 Mn1 2.5903(14) 1_655 ? C33 N8 1.4657(16) . ? C33 C34 1.5139(16) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? O5 C5 1.2081(16) . ? Mn1 O1 2.1472(10) . ? Mn1 O1 2.1842(13) 2_667 ? Mn1 O7 2.2316(10) 1_455 ? Mn1 O6 2.2440(10) 1_455 ? Mn1 O8 2.2562(11) . ? Mn1 O9 2.2972(11) . ? Mn1 C11 2.5903(14) 1_455 ? Mn2 O17 2.1629(10) 2_576 ? Mn2 O20 2.1731(10) 2_667 ? Mn2 O15 2.1789(16) 1_455 ? Mn2 O2W 2.2465(11) . ? Mn2 N10 2.2482(12) . ? Mn3 O21 2.1144(11) 2_667 ? Mn3 O3W 2.1226(17) . ? Mn3 O13 2.2008(10) . ? Mn3 O15 2.2227(12) 1_455 ? Mn3 N7 2.2612(12) . ? Mn3 O16 2.3455(11) 1_455 ? Mn3 C23 2.6313(13) 1_455 ? O13 C21 1.2638(14) . ? N3 C5 1.3781(17) . ? N3 C6 1.3803(16) . ? N3 C7 1.4857(15) . ? O4 C6 1.2136(15) . ? O11 C16 1.2092(15) . ? O2W H2WA 0.8200 . ? O2W H2WB 0.948(10) . ? O9 C12 1.2420(13) . ? O1 C1 1.2978(13) . ? O1 Mn1 2.1842(13) 2_667 ? N2 C4 1.3764(16) . ? N2 C6 1.3840(15) . ? N2 C3 1.4858(16) . ? N5 C15 1.3773(16) . ? N5 C17 1.3872(16) . ? N5 C14 1.4845(16) . ? O12 C17 1.2031(15) . ? N4 C16 1.3795(15) . ? N4 C15 1.3832(16) . ? N4 C18 1.4711(15) . ? O8 C12 1.2579(13) . ? N8 C26 1.3597(16) . ? N8 C28 1.3810(16) . ? C7 C8 1.5183(15) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N1 C5 1.3830(16) . ? N1 C4 1.3895(16) . ? N1 C9 1.4772(17) . ? O3 C4 1.2063(16) . ? N6 C17 1.3773(16) . ? N6 C16 1.3811(16) . ? N6 C19 1.4757(16) . ? N7 C26 1.3125(17) . ? N7 C27 1.3898(17) . ? C21 C20 1.5141(17) . ? C35 C36 1.5100(16) . ? C35 C34 1.5208(16) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? N9 C38 1.3461(16) . ? N9 C40 1.3836(17) . ? N9 C37 1.4664(16) . ? O10 C15 1.2087(15) . ? O3W H3WA 0.8200 . ? O3W H3WB 0.836(12) . ? C9 C10 1.5054(15) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C12 C13 1.5138(17) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? N10 C38 1.3180(16) . ? N10 C39 1.3960(16) . ? C1 O2 1.2143(14) . ? C1 C2 1.5089(17) . ? C28 C32 1.3862(18) . ? C28 C27 1.3976(18) . ? C19 C20 1.5055(16) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C27 C29 1.390(2) . ? C3 C2 1.5191(15) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C26 H26 0.9300 . ? C40 C44 1.3823(18) . ? C40 C39 1.4051(17) . ? C37 C36 1.5220(16) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C39 C41 1.3886(19) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C38 H38 0.9300 . ? C14 C13 1.5103(16) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C41 C42 1.377(2) . ? C41 H41 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C32 C31 1.367(2) . ? C32 H32 0.9300 . ? C44 C43 1.384(2) . ? C44 H44 0.9300 . ? C42 C43 1.404(2) . ? C42 H42 0.9300 . ? C29 C30 1.379(2) . ? C29 H29 0.9300 . ? C31 C30 1.398(2) . ? C31 H31 0.9300 . ? C43 H43 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C30 H30 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 C21 O17 Mn2 135.79(8) . 2_576 ? C23 O16 Mn3 88.90(8) . 1_655 ? C23 O15 Mn2 143.76(7) . 1_655 ? C23 O15 Mn3 93.77(7) . 1_655 ? Mn2 O15 Mn3 122.46(6) 1_655 1_655 ? Mn2 O1W H1WA 109.5 . . ? Mn2 O1W H1WB 118.8(9) . . ? H1WA O1W H1WB 127.2 . . ? O16 C23 O15 119.68(11) . . ? O16 C23 C24 120.76(10) . . ? O15 C23 C24 119.42(8) . . ? O16 C23 Mn3 63.03(7) . 1_655 ? O15 C23 Mn3 57.45(6) . 1_655 ? C24 C23 Mn3 166.90(9) . 1_655 ? C23 C24 C18 112.39(8) . . ? C23 C24 H24A 109.1 . . ? C18 C24 H24A 109.1 . . ? C23 C24 H24B 109.1 . . ? C18 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? C22 O21 Mn3 131.46(9) . 2_667 ? C22 O20 Mn2 132.90(7) . 2_667 ? O20 C22 O21 125.77(11) . . ? O20 C22 C8 119.36(9) . . ? O21 C22 C8 114.86(9) . . ? C11 O7 Mn1 91.33(7) . 1_655 ? C11 O6 Mn1 91.21(8) . 1_655 ? O6 C11 O7 119.40(12) . . ? O6 C11 C10 120.06(10) . . ? O7 C11 C10 120.54(9) . . ? O6 C11 Mn1 60.01(7) . 1_655 ? O7 C11 Mn1 59.46(7) . 1_655 ? C10 C11 Mn1 177.00(8) . 1_655 ? N8 C33 C34 113.12(9) . . ? N8 C33 H33A 109.0 . . ? C34 C33 H33A 109.0 . . ? N8 C33 H33B 109.0 . . ? C34 C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? O1 Mn1 O1 76.07(4) . 2_667 ? O1 Mn1 O7 96.42(4) . 1_455 ? O1 Mn1 O7 108.79(5) 2_667 1_455 ? O1 Mn1 O6 147.18(4) . 1_455 ? O1 Mn1 O6 92.26(5) 2_667 1_455 ? O7 Mn1 O6 57.96(4) 1_455 1_455 ? O1 Mn1 O8 113.32(4) . . ? O1 Mn1 O8 91.71(5) 2_667 . ? O7 Mn1 O8 147.42(4) 1_455 . ? O6 Mn1 O8 97.35(4) 1_455 . ? O1 Mn1 O9 110.33(4) . . ? O1 Mn1 O9 148.01(3) 2_667 . ? O7 Mn1 O9 101.71(5) 1_455 . ? O6 Mn1 O9 95.88(5) 1_455 . ? O8 Mn1 O9 56.60(5) . . ? O1 Mn1 C11 122.77(4) . 1_455 ? O1 Mn1 C11 101.02(4) 2_667 1_455 ? O7 Mn1 C11 29.21(3) 1_455 1_455 ? O6 Mn1 C11 28.78(3) 1_455 1_455 ? O8 Mn1 C11 123.90(4) . 1_455 ? O9 Mn1 C11 100.91(4) . 1_455 ? O1W Mn2 O17 88.15(4) . 2_576 ? O1W Mn2 O20 94.08(4) . 2_667 ? O17 Mn2 O20 173.80(3) 2_576 2_667 ? O1W Mn2 O15 176.40(4) . 1_455 ? O17 Mn2 O15 88.25(4) 2_576 1_455 ? O20 Mn2 O15 89.47(4) 2_667 1_455 ? O1W Mn2 O2W 90.34(5) . . ? O17 Mn2 O2W 88.54(4) 2_576 . ? O20 Mn2 O2W 85.67(4) 2_667 . ? O15 Mn2 O2W 89.34(5) 1_455 . ? O1W Mn2 N10 89.44(5) . . ? O17 Mn2 N10 96.65(4) 2_576 . ? O20 Mn2 N10 89.15(4) 2_667 . ? O15 Mn2 N10 91.20(5) 1_455 . ? O2W Mn2 N10 174.79(4) . . ? O21 Mn3 O3W 131.54(4) 2_667 . ? O21 Mn3 O13 87.93(4) 2_667 . ? O3W Mn3 O13 85.11(4) . . ? O21 Mn3 O15 92.04(6) 2_667 1_455 ? O3W Mn3 O15 135.68(5) . 1_455 ? O13 Mn3 O15 89.54(4) . 1_455 ? O21 Mn3 N7 89.71(4) 2_667 . ? O3W Mn3 N7 90.56(5) . . ? O13 Mn3 N7 171.76(3) . . ? O15 Mn3 N7 98.43(4) 1_455 . ? O21 Mn3 O16 147.63(3) 2_667 1_455 ? O3W Mn3 O16 80.76(4) . 1_455 ? O13 Mn3 O16 98.65(4) . 1_455 ? O15 Mn3 O16 56.61(4) 1_455 1_455 ? N7 Mn3 O16 87.54(4) . 1_455 ? O21 Mn3 C23 119.83(5) 2_667 1_455 ? O3W Mn3 C23 108.63(5) . 1_455 ? O13 Mn3 C23 97.42(4) . 1_455 ? O15 Mn3 C23 28.79(3) 1_455 1_455 ? N7 Mn3 C23 90.60(4) . 1_455 ? O16 Mn3 C23 28.07(3) 1_455 1_455 ? C21 O13 Mn3 132.38(7) . . ? C5 N3 C6 124.31(10) . . ? C5 N3 C7 117.16(10) . . ? C6 N3 C7 118.22(10) . . ? Mn2 O2W H2WA 109.5 . . ? Mn2 O2W H2WB 103.9(10) . . ? H2WA O2W H2WB 108.8 . . ? C12 O9 Mn1 91.13(8) . . ? C1 O1 Mn1 121.56(7) . . ? C1 O1 Mn1 133.41(8) . 2_667 ? Mn1 O1 Mn1 103.93(4) . 2_667 ? C4 N2 C6 123.61(10) . . ? C4 N2 C3 117.37(10) . . ? C6 N2 C3 118.94(10) . . ? C15 N5 C17 123.96(10) . . ? C15 N5 C14 118.90(10) . . ? C17 N5 C14 117.14(10) . . ? C16 N4 C15 124.19(10) . . ? C16 N4 C18 118.37(10) . . ? C15 N4 C18 117.42(10) . . ? C12 O8 Mn1 92.62(8) . . ? O4 C6 N3 120.92(11) . . ? O4 C6 N2 122.91(11) . . ? N3 C6 N2 116.18(10) . . ? C26 N8 C28 105.97(10) . . ? C26 N8 C33 126.13(11) . . ? C28 N8 C33 127.89(10) . . ? N3 C7 C8 111.65(9) . . ? N3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C5 N1 C4 124.08(11) . . ? C5 N1 C9 117.64(10) . . ? C4 N1 C9 118.23(10) . . ? O5 C5 N3 122.63(12) . . ? O5 C5 N1 121.85(12) . . ? N3 C5 N1 115.52(11) . . ? C17 N6 C16 124.67(10) . . ? C17 N6 C19 117.39(10) . . ? C16 N6 C19 117.94(10) . . ? C26 N7 C27 104.54(10) . . ? C26 N7 Mn3 126.04(8) . . ? C27 N7 Mn3 128.88(9) . . ? O17 C21 O13 124.30(11) . . ? O17 C21 C20 116.09(10) . . ? O13 C21 C20 119.61(10) . . ? C36 C35 C34 113.19(11) . . ? C36 C35 H35A 108.9 . . ? C34 C35 H35A 108.9 . . ? C36 C35 H35B 108.9 . . ? C34 C35 H35B 108.9 . . ? H35A C35 H35B 107.8 . . ? C38 N9 C40 106.63(10) . . ? C38 N9 C37 124.97(11) . . ? C40 N9 C37 128.33(10) . . ? O11 C16 N4 121.89(11) . . ? O11 C16 N6 122.73(11) . . ? N4 C16 N6 115.39(10) . . ? Mn3 O3W H3WA 109.5 . . ? Mn3 O3W H3WB 137.5(9) . . ? H3WA O3W H3WB 113.0 . . ? N1 C9 C10 112.49(9) . . ? N1 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N1 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? O9 C12 O8 119.46(12) . . ? O9 C12 C13 121.50(9) . . ? O8 C12 C13 119.04(9) . . ? C33 C34 C35 113.88(11) . . ? C33 C34 H34A 108.8 . . ? C35 C34 H34A 108.8 . . ? C33 C34 H34B 108.8 . . ? C35 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? O10 C15 N5 122.49(11) . . ? O10 C15 N4 121.55(11) . . ? N5 C15 N4 115.96(10) . . ? C38 N10 C39 104.78(10) . . ? C38 N10 Mn2 119.65(8) . . ? C39 N10 Mn2 135.57(8) . . ? O2 C1 O1 122.28(12) . . ? O2 C1 C2 121.02(9) . . ? O1 C1 C2 116.69(9) . . ? N8 C28 C32 131.33(12) . . ? N8 C28 C27 105.87(11) . . ? C32 C28 C27 122.81(12) . . ? N6 C19 C20 111.72(9) . . ? N6 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? N6 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? N7 C27 C29 130.38(12) . . ? N7 C27 C28 109.59(11) . . ? C29 C27 C28 119.97(12) . . ? N2 C3 C2 110.44(9) . . ? N2 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? N2 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C1 C2 C3 113.56(9) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N7 C26 N8 114.02(11) . . ? N7 C26 H26 123.0 . . ? N8 C26 H26 123.0 . . ? N9 C40 C44 131.89(12) . . ? N9 C40 C39 105.71(11) . . ? C44 C40 C39 122.40(12) . . ? O3 C4 N2 121.97(12) . . ? O3 C4 N1 121.92(12) . . ? N2 C4 N1 116.11(10) . . ? O12 C17 N6 122.45(11) . . ? O12 C17 N5 121.94(11) . . ? N6 C17 N5 115.58(11) . . ? N9 C37 C36 112.93(9) . . ? N9 C37 H37A 109.0 . . ? C36 C37 H37A 109.0 . . ? N9 C37 H37B 109.0 . . ? C36 C37 H37B 109.0 . . ? H37A C37 H37B 107.8 . . ? N4 C18 C24 113.12(8) . . ? N4 C18 H18A 109.0 . . ? C24 C18 H18A 109.0 . . ? N4 C18 H18B 109.0 . . ? C24 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C41 C39 N10 130.42(12) . . ? C41 C39 C40 120.63(12) . . ? N10 C39 C40 108.95(11) . . ? C19 C20 C21 109.30(9) . . ? C19 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? C19 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? N10 C38 N9 113.92(11) . . ? N10 C38 H38 123.0 . . ? N9 C38 H38 123.0 . . ? N5 C14 C13 110.73(9) . . ? N5 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? N5 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C13 C12 113.65(9) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C35 C36 C37 114.33(11) . . ? C35 C36 H36A 108.7 . . ? C37 C36 H36A 108.7 . . ? C35 C36 H36B 108.7 . . ? C37 C36 H36B 108.7 . . ? H36A C36 H36B 107.6 . . ? C42 C41 C39 117.46(13) . . ? C42 C41 H41 121.3 . . ? C39 C41 H41 121.3 . . ? C9 C10 C11 111.33(9) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C31 C32 C28 116.64(13) . . ? C31 C32 H32 121.7 . . ? C28 C32 H32 121.7 . . ? C40 C44 C43 116.11(13) . . ? C40 C44 H44 121.9 . . ? C43 C44 H44 121.9 . . ? C41 C42 C43 121.23(14) . . ? C41 C42 H42 119.4 . . ? C43 C42 H42 119.4 . . ? C30 C29 C27 116.98(13) . . ? C30 C29 H29 121.5 . . ? C27 C29 H29 121.5 . . ? C32 C31 C30 121.23(15) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C44 C43 C42 122.15(14) . . ? C44 C43 H43 118.9 . . ? C42 C43 H43 118.9 . . ? C22 C8 C7 117.17(9) . . ? C22 C8 H8A 108.0 . . ? C7 C8 H8A 108.0 . . ? C22 C8 H8B 108.0 . . ? C7 C8 H8B 108.0 . . ? H8A C8 H8B 107.2 . . ? C29 C30 C31 122.31(15) . . ? C29 C30 H30 118.8 . . ? C31 C30 H30 118.8 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.099 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 907895' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H50 Mn3 N10 O22' _chemical_formula_weight 1211.74 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' _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 13.527(3) _cell_length_b 14.982(3) _cell_length_c 15.036(3) _cell_angle_alpha 62.09(3) _cell_angle_beta 67.21(3) _cell_angle_gamma 74.82(3) _cell_volume 2470.4(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7906 _cell_measurement_theta_min 1.5456 _cell_measurement_theta_max 29.1292 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1246 _exptl_absorpt_coefficient_mu 0.849 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7102 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 ; Saturn724 (4x4 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20504 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8600 _reflns_number_gt 7389 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1055P)^2^+6.6261P] 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 8600 _refine_ls_number_parameters 717 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.2168 _refine_ls_wR_factor_gt 0.2068 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.131 _refine_ls_shift/su_mean 0.013 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 O15 O 0.89761(12) 0.53506(11) 0.54999(12) 0.0746(6) Uani 1 1 d U . . C19 C 0.64805(16) 0.46302(17) 0.74338(17) 0.0791(7) Uani 1 1 d DU . . H19A H 0.6639 0.4544 0.8047 0.095 Uiso 1 1 calc R A 1 H19B H 0.6637 0.3969 0.7413 0.095 Uiso 1 1 calc R A 1 Mn1 Mn -0.023849(15) 0.802343(14) 1.003617(15) 0.02941(6) Uani 1 1 d . . . Mn2 Mn 0.144748(16) 0.994842(15) 0.735319(15) 0.03192(7) Uani 1 1 d . . . Mn3 Mn -0.838642(19) 1.325511(17) 1.551769(18) 0.04324(8) Uani 1 1 d . . . C1 C -0.74819(12) 1.16346(11) 1.50180(12) 0.0409(5) Uani 1 1 d . . . C2 C -0.69481(17) 1.09675(12) 1.44417(12) 0.0547(7) Uani 1 1 d . . . H2A H -0.7348 1.0381 1.4779 0.066 Uiso 1 1 calc R . . H2B H -0.6229 1.0725 1.4503 0.066 Uiso 1 1 calc R . . C3 C -0.68668(13) 1.14851(12) 1.32801(12) 0.0431(5) Uani 1 1 d . . . H3A H -0.7573 1.1795 1.3208 0.052 Uiso 1 1 calc R . . H3B H -0.6391 1.2019 1.2917 0.052 Uiso 1 1 calc R . . C4 C -0.92889(10) 0.98703(10) 1.19635(10) 0.0295(4) Uani 1 1 d . . . C5 C -0.80911(12) 0.97342(13) 1.14955(12) 0.0441(5) Uani 1 1 d . . . H5A H -0.7825 1.0398 1.1109 0.053 Uiso 1 1 calc R . . H5B H -0.7932 0.9449 1.0988 0.053 Uiso 1 1 calc R . . C6 C -0.74696(11) 0.90592(12) 1.22834(12) 0.0423(5) Uani 1 1 d . . . H6A H -0.7977 0.8780 1.2988 0.051 Uiso 1 1 calc R . . H6B H -0.7062 0.8498 1.2102 0.051 Uiso 1 1 calc R . . C7 C -0.20390(10) 0.89450(10) 1.15667(10) 0.0306(4) Uani 1 1 d . . . C8 C -0.32441(11) 0.90988(12) 1.21249(11) 0.0375(5) Uani 1 1 d . . . H8A H -0.3554 0.8459 1.2468 0.045 Uiso 1 1 calc R . . H8B H -0.3347 0.9324 1.2666 0.045 Uiso 1 1 calc R . . C9 C -0.38063(11) 0.98698(12) 1.13476(12) 0.0400(5) Uani 1 1 d . . . H9A H -0.3521 1.0518 1.1036 0.048 Uiso 1 1 calc R . . H9B H -0.3661 0.9663 1.0783 0.048 Uiso 1 1 calc R . . C10 C -0.53530(12) 1.06216(11) 1.23736(11) 0.0379(5) Uani 1 1 d . . . C11 C -0.56336(11) 0.94796(11) 1.17737(12) 0.0407(5) Uani 1 1 d . . . C12 C -0.71704(12) 1.02737(12) 1.27739(11) 0.0394(5) Uani 1 1 d . . . C13 C 0.22104(11) 0.78374(11) 0.87623(11) 0.0388(4) Uani 1 1 d . . . C14 C 0.32273(14) 0.71369(14) 0.88728(17) 0.0624(8) Uani 1 1 d . . . H14A H 0.3479 0.7231 0.9343 0.075 Uiso 1 1 calc R . . H14B H 0.3774 0.7344 0.8185 0.075 Uiso 1 1 calc R . . C15 C 0.31380(12) 0.60153(11) 0.92866(12) 0.0409(5) Uani 1 1 d . . . H15A H 0.3413 0.5653 0.9886 0.049 Uiso 1 1 calc R . . H15B H 0.2381 0.5914 0.9546 0.049 Uiso 1 1 calc R . . C16 C 0.25555(17) 0.37017(15) 0.64102(17) 0.0907(7) Uani 1 1 d . . . C17 C 0.3022(2) 0.3852(2) 0.7267(2) 0.1062(14) Uani 1 1 d . . . H17A H 0.2471 0.3802 0.7931 0.127 Uiso 1 1 calc R . . H17B H 0.3662 0.3404 0.7393 0.127 Uiso 1 1 calc R . . C18 C 0.3230(2) 0.4825(3) 0.6571(3) 0.1272(17) Uani 1 1 d . . . H18A H 0.2587 0.5284 0.6476 0.153 Uiso 1 1 calc R . . H18B H 0.3756 0.4881 0.5894 0.153 Uiso 1 1 calc R . . C22 C 0.48279(18) 0.4630(2) 0.71649(18) 0.1444(8) Uani 1 1 d . . . C23 C 0.31285(15) 0.53584(16) 0.80813(15) 0.0765(7) Uani 1 1 d . . . C24 C 0.48081(13) 0.53611(14) 0.83231(13) 0.0574(6) Uani 1 1 d . . . C25 C 0.08355(13) 0.88911(11) 0.62394(11) 0.0420(5) Uani 1 1 d . . . H25 H 0.0126 0.9162 0.6448 0.050 Uiso 1 1 calc R . . C26 C 0.25342(13) 0.85073(11) 0.60084(12) 0.0413(5) Uani 1 1 d . . . C27 C 0.22511(14) 0.80579(11) 0.55199(12) 0.0424(5) Uani 1 1 d . . . C28 C 0.35916(14) 0.83965(14) 0.59818(15) 0.0536(7) Uani 1 1 d . . . H28 H 0.3790 0.8681 0.6313 0.064 Uiso 1 1 calc R . . C29 C 0.43460(17) 0.78457(15) 0.54434(18) 0.0676(9) Uani 1 1 d . . . H29 H 0.5066 0.7773 0.5399 0.081 Uiso 1 1 calc R . . C30 C 0.40451(18) 0.74003(15) 0.49684(17) 0.0693(9) Uani 1 1 d . . . H30 H 0.4569 0.7025 0.4625 0.083 Uiso 1 1 calc R . . C31 C 0.30006(17) 0.74981(13) 0.49918(14) 0.0587(7) Uani 1 1 d . . . H31 H 0.2805 0.7203 0.4669 0.070 Uiso 1 1 calc R . . C32 C 0.04375(14) 0.79356(13) 0.54457(12) 0.0533(6) Uani 1 1 d . . . H32A H 0.0869 0.7591 0.4990 0.064 Uiso 1 1 calc R . . H32B H 0.0006 0.8507 0.5063 0.064 Uiso 1 1 calc R . . C33 C -0.02987(13) 0.72150(12) 0.64314(12) 0.0480(5) Uani 1 1 d . . . H33A H -0.0789 0.7028 0.6230 0.058 Uiso 1 1 calc R . . H33B H -0.0728 0.7566 0.6882 0.058 Uiso 1 1 calc R . . C34 C 0.02819(14) 0.62566(12) 0.70623(12) 0.0479(5) Uani 1 1 d . . . H34A H 0.0873 0.6439 0.7139 0.057 Uiso 1 1 calc R . . H34B H 0.0588 0.5836 0.6669 0.057 Uiso 1 1 calc R . . C35 C -0.04306(14) 0.56449(11) 0.81476(12) 0.0503(5) Uani 1 1 d . . . H35A H -0.0998 0.5423 0.8077 0.060 Uiso 1 1 calc R . . H35B H -0.0008 0.5046 0.8507 0.060 Uiso 1 1 calc R . . C36 C -0.03772(12) 0.66028(12) 0.91203(12) 0.0463(5) Uani 1 1 d . . . H36 H 0.0361 0.6456 0.9010 0.056 Uiso 1 1 calc R . . C37 C -0.19901(11) 0.66058(10) 0.91090(10) 0.0343(4) Uani 1 1 d . . . C38 C -0.20208(11) 0.71836(10) 0.96276(10) 0.0339(4) Uani 1 1 d . . . C39 C -0.30030(12) 0.76486(11) 1.00645(11) 0.0385(5) Uani 1 1 d . . . H39 H -0.3041 0.8031 1.0420 0.046 Uiso 1 1 calc R . . C40 C -0.39166(13) 0.75212(12) 0.99505(12) 0.0436(5) Uani 1 1 d . . . H40 H -0.4579 0.7830 1.0228 0.052 Uiso 1 1 calc R . . C41 C -0.38704(12) 0.69408(12) 0.94288(12) 0.0453(5) Uani 1 1 d . . . H41 H -0.4502 0.6865 0.9373 0.054 Uiso 1 1 calc R . . C42 C -0.29077(12) 0.64783(11) 0.89952(11) 0.0391(5) Uani 1 1 d . . . H42 H -0.2873 0.6097 0.8641 0.047 Uiso 1 1 calc R . . N1 N -0.09889(10) 0.71800(9) 0.96138(9) 0.0407(4) Uani 1 1 d . . . N2 N -0.09182(10) 0.62456(9) 0.87909(9) 0.0402(4) Uani 1 1 d . . . N3 N 0.11521(11) 0.83102(10) 0.56949(9) 0.0437(4) Uani 1 1 d . . . N4 N 0.16193(10) 0.90410(9) 0.64500(10) 0.0417(4) Uani 1 1 d . . . N5 N -0.49805(9) 0.99927(9) 1.18470(9) 0.0370(4) Uani 1 1 d . . . N6 N -0.67304(9) 0.96152(9) 1.22899(9) 0.0371(4) Uani 1 1 d . . . N7 N -0.64543(9) 1.07625(9) 1.27876(9) 0.0368(4) Uani 1 1 d . . . N8 N 0.36987(10) 0.55633(11) 0.85320(10) 0.0504(4) Uani 1 1 d . B . N9 N 0.53271(12) 0.48919(14) 0.76394(13) 0.0828(6) Uani 1 1 d U B . N10 N 0.37350(13) 0.49132(15) 0.73778(14) 0.1327(6) Uani 1 1 d . B . O1 O -0.78415(9) 1.12650(8) 1.60057(8) 0.0473(4) Uani 1 1 d . . . O2 O -0.75621(11) 1.25788(8) 1.44668(9) 0.0553(4) Uani 1 1 d . . . O3 O -0.97803(8) 0.92387(7) 1.28461(8) 0.0374(3) Uani 1 1 d . . . O4 O -0.98172(8) 1.06171(8) 1.14451(8) 0.0425(4) Uani 1 1 d . . . O5 O -0.17774(7) 0.85420(7) 1.09347(7) 0.0372(3) Uani 1 1 d . . . O6 O -0.13773(8) 0.92342(8) 1.17493(7) 0.0438(3) Uani 1 1 d . . . O7 O -0.81401(9) 1.04006(10) 1.31722(10) 0.0563(4) Uani 1 1 d . . . O8 O -0.47559(9) 1.10275(9) 1.24574(10) 0.0622(4) Uani 1 1 d . . . O9 O -0.52818(9) 0.89345(9) 1.13128(10) 0.0676(4) Uani 1 1 d . . . O10 O 0.13290(8) 0.74532(8) 0.92903(9) 0.0491(4) Uani 1 1 d . . . O11 O 0.23324(8) 0.87539(8) 0.82344(9) 0.0465(4) Uani 1 1 d . . . O12 O 0.31168(13) 0.34704(14) 0.56629(14) 0.1295(7) Uani 1 1 d . . . O13 O 0.16170(12) 0.37036(13) 0.66772(10) 0.0952(6) Uani 1 1 d . . . O16 O 0.52896(9) 0.56080(9) 0.86820(9) 0.0578(4) Uani 1 1 d . B . O17 O 0.53198(15) 0.42162(15) 0.65824(14) 0.2037(7) Uani 1 1 d . B . O18 O 0.21624(10) 0.55121(12) 0.82931(11) 0.0874(5) Uani 1 1 d . B . O1W O 0.05638(8) 0.88502(7) 1.04337(7) 0.0389(3) Uani 1 1 d . . . H1WA H 0.0113 0.9075 1.0851 0.058 Uiso 1 1 calc R . . O2W O -0.00815(10) 0.67060(9) 1.14863(9) 0.0536(4) Uani 1 1 d D . . H2WA H 0.0483 0.6699 1.1574 0.080 Uiso 1 1 calc R . . O3W O -0.99410(10) 1.27621(9) 1.62908(11) 0.0614(5) Uani 1 1 d . . . H3WA H -1.0359 1.3181 1.6499 0.092 Uiso 1 1 calc R . . O14 O 0.86098(13) 0.39188(14) 0.72435(15) 0.1002(8) Uani 1 1 d U . . C21 C 0.8335(3) 0.4814(3) 0.6420(3) 0.0752(10) Uani 0.506(2) 1 d PDU B 1 C21B C 0.7765(2) 0.3258(3) 0.8094(2) 0.0445(11) Uani 0.494(2) 1 d P B 2 H21A H 0.7858 0.3075 0.8768 0.053 Uiso 0.506(2) 1 calc PR B 2 H21B H 0.7878 0.2637 0.8000 0.053 Uiso 0.494(2) 1 calc PR B 2 C20 C 0.7167(3) 0.5206(4) 0.6609(4) 0.0858(14) Uani 0.506(2) 1 d PDU B 1 C20B C 0.6612(2) 0.3706(3) 0.8150(2) 0.0506(11) Uani 0.494(2) 1 d PD B 2 H20A H 0.6260 0.3261 0.8088 0.061 Uiso 0.506(2) 1 calc PR B 2 H20B H 0.6245 0.3711 0.8845 0.061 Uiso 0.494(2) 1 calc PR B 2 H3WB H -0.9980(15) 1.2191(14) 1.6744(14) 0.061 Uiso 1 1 d . . . H1WB H 0.1132(15) 0.8532(13) 1.0508(13) 0.061 Uiso 1 1 d . . . H2WB H -0.0618(8) 0.6670(12) 1.2008(7) 0.061 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O15 0.0520(7) 0.0642(7) 0.0821(8) -0.0271(6) -0.0058(6) 0.0044(6) C19 0.0551(9) 0.1041(9) 0.1020(9) -0.0693(6) -0.0225(7) 0.0045(8) Mn1 0.02415(8) 0.03400(8) 0.03732(7) -0.02187(5) -0.00851(6) -0.00160(7) Mn2 0.02630(9) 0.03816(9) 0.03519(8) -0.02001(6) -0.00591(6) -0.00528(7) Mn3 0.04214(11) 0.04645(10) 0.05031(9) -0.02694(7) -0.01487(8) -0.00403(9) C1 0.0374(7) 0.0390(6) 0.0516(6) -0.0241(4) -0.0123(5) -0.0036(5) C2 0.0763(12) 0.0351(7) 0.0355(7) -0.0134(5) -0.0081(7) 0.0041(8) C3 0.0392(8) 0.0415(7) 0.0432(6) -0.0224(5) -0.0095(5) 0.0093(6) C4 0.0285(6) 0.0334(5) 0.0329(5) -0.0164(4) -0.0111(4) -0.0050(4) C5 0.0293(6) 0.0614(8) 0.0409(6) -0.0189(5) -0.0102(5) -0.0088(6) C6 0.0321(6) 0.0480(7) 0.0517(6) -0.0189(5) -0.0176(5) -0.0078(5) C7 0.0229(6) 0.0356(6) 0.0333(5) -0.0159(4) -0.0081(4) -0.0007(5) C8 0.0266(6) 0.0475(7) 0.0394(6) -0.0223(4) -0.0083(5) 0.0004(5) C9 0.0244(6) 0.0488(7) 0.0447(6) -0.0225(5) -0.0042(5) -0.0040(6) C10 0.0290(6) 0.0434(6) 0.0411(6) -0.0221(4) -0.0050(5) -0.0034(5) C11 0.0276(6) 0.0459(7) 0.0531(6) -0.0264(5) -0.0161(5) 0.0066(6) C12 0.0275(6) 0.0469(7) 0.0426(6) -0.0194(5) -0.0110(5) 0.0003(6) C13 0.0278(6) 0.0557(6) 0.0477(5) -0.0369(4) -0.0126(4) 0.0050(5) C14 0.0400(8) 0.0460(9) 0.0880(11) -0.0188(8) -0.0241(7) 0.0054(7) C15 0.0310(6) 0.0443(7) 0.0500(6) -0.0225(5) -0.0133(5) -0.0005(6) C16 0.0675(10) 0.1117(9) 0.1602(9) -0.1097(6) -0.0558(7) 0.0238(8) C17 0.0767(15) 0.0749(16) 0.1012(19) 0.0161(15) -0.0221(13) -0.0169(13) C18 0.0620(14) 0.112(2) 0.106(2) 0.0328(18) -0.0246(13) -0.0054(15) C22 0.0523(10) 0.2896(13) 0.2228(9) -0.2266(7) -0.0428(7) 0.0169(9) C23 0.0396(8) 0.1268(10) 0.1071(8) -0.0855(6) -0.0275(6) 0.0044(8) C24 0.0363(7) 0.0890(9) 0.0679(7) -0.0532(5) -0.0143(5) -0.0004(7) C25 0.0365(7) 0.0483(7) 0.0443(6) -0.0251(5) -0.0059(5) -0.0072(6) C26 0.0405(7) 0.0387(6) 0.0411(6) -0.0173(5) -0.0056(5) -0.0074(6) C27 0.0485(8) 0.0341(6) 0.0401(6) -0.0149(5) -0.0086(6) -0.0061(6) C28 0.0404(8) 0.0477(8) 0.0643(9) -0.0219(6) -0.0105(7) -0.0028(7) C29 0.0465(10) 0.0563(10) 0.0834(12) -0.0253(8) -0.0099(9) -0.0020(8) C30 0.0616(12) 0.0601(9) 0.0726(10) -0.0352(7) -0.0045(9) 0.0048(9) C31 0.0758(12) 0.0467(8) 0.0485(7) -0.0256(5) -0.0095(7) -0.0015(8) C32 0.0631(8) 0.0631(8) 0.0483(6) -0.0258(5) -0.0235(5) -0.0134(7) C33 0.0399(7) 0.0580(7) 0.0655(6) -0.0384(5) -0.0243(5) 0.0028(6) C34 0.0432(8) 0.0596(7) 0.0540(6) -0.0397(4) -0.0109(5) 0.0002(6) C35 0.0549(8) 0.0551(6) 0.0612(6) -0.0416(4) -0.0160(5) -0.0054(6) C36 0.0339(7) 0.0634(7) 0.0606(6) -0.0420(4) -0.0114(5) -0.0069(5) C37 0.0413(6) 0.0293(5) 0.0355(5) -0.0108(4) -0.0140(4) -0.0100(5) C38 0.0359(6) 0.0344(5) 0.0387(5) -0.0178(4) -0.0115(4) -0.0093(5) C39 0.0416(7) 0.0404(6) 0.0398(5) -0.0202(4) -0.0087(5) -0.0125(5) C40 0.0361(7) 0.0444(7) 0.0496(7) -0.0203(5) -0.0084(5) -0.0087(6) C41 0.0411(6) 0.0507(7) 0.0537(6) -0.0204(5) -0.0196(5) -0.0140(5) C42 0.0490(7) 0.0362(6) 0.0416(5) -0.0156(4) -0.0182(4) -0.0133(5) N1 0.0355(6) 0.0504(5) 0.0492(5) -0.0315(3) -0.0103(4) -0.0072(4) N2 0.0392(6) 0.0446(5) 0.0479(5) -0.0292(3) -0.0101(4) -0.0067(4) N3 0.0489(6) 0.0487(6) 0.0397(5) -0.0237(4) -0.0096(4) -0.0102(5) N4 0.0371(6) 0.0470(5) 0.0484(5) -0.0279(4) -0.0089(4) -0.0063(5) N5 0.0231(5) 0.0474(5) 0.0450(5) -0.0268(4) -0.0081(4) 0.0013(4) N6 0.0232(5) 0.0452(5) 0.0496(5) -0.0260(4) -0.0144(4) 0.0039(4) N7 0.0233(5) 0.0482(5) 0.0436(5) -0.0283(4) -0.0069(4) 0.0020(4) N8 0.0287(5) 0.0847(7) 0.0622(5) -0.0512(4) -0.0158(4) 0.0006(5) N9 0.0380(7) 0.1442(9) 0.1131(7) -0.1013(5) -0.0193(5) 0.0066(7) N10 0.0421(7) 0.2737(10) 0.2053(7) -0.2093(5) -0.0415(5) 0.0158(7) O1 0.0504(6) 0.0565(5) 0.0388(4) -0.0257(3) -0.0021(4) -0.0178(4) O2 0.0667(7) 0.0417(5) 0.0567(5) -0.0262(4) -0.0145(5) 0.0004(5) O3 0.0294(4) 0.0395(4) 0.0397(4) -0.0119(3) -0.0088(3) -0.0098(4) O4 0.0334(5) 0.0476(5) 0.0391(4) -0.0097(4) -0.0145(3) -0.0032(4) O5 0.0252(4) 0.0537(4) 0.0457(4) -0.0344(3) -0.0076(3) -0.0021(3) O6 0.0269(4) 0.0712(4) 0.0549(4) -0.0476(3) -0.0051(3) -0.0080(4) O7 0.0215(5) 0.0781(6) 0.0710(6) -0.0426(4) -0.0062(4) 0.0030(5) O8 0.0353(5) 0.0715(5) 0.1002(6) -0.0578(4) -0.0090(4) -0.0115(4) O9 0.0383(5) 0.0933(5) 0.1089(6) -0.0804(4) -0.0182(4) 0.0039(5) O10 0.0216(4) 0.0587(5) 0.0776(5) -0.0478(3) -0.0031(4) -0.0009(4) O11 0.0391(5) 0.0359(5) 0.0637(5) -0.0176(4) -0.0227(4) 0.0023(4) O12 0.0550(7) 0.2048(10) 0.2186(9) -0.1655(6) -0.0457(6) 0.0066(7) O13 0.0805(7) 0.1655(10) 0.0751(6) -0.0688(5) -0.0206(5) -0.0352(7) O16 0.0377(5) 0.0876(6) 0.0771(5) -0.0552(3) -0.0232(4) -0.0012(4) O17 0.0672(9) 0.4119(10) 0.3276(8) -0.3438(5) -0.0480(6) 0.0283(8) O18 0.0391(5) 0.1437(8) 0.1328(6) -0.1015(5) -0.0378(4) 0.0127(5) O1W 0.0290(4) 0.0481(4) 0.0509(4) -0.0317(3) -0.0117(3) -0.0004(4) O2W 0.0552(6) 0.0447(5) 0.0575(5) -0.0125(4) -0.0250(4) -0.0051(5) O3W 0.0515(6) 0.0417(5) 0.0819(7) -0.0259(5) -0.0100(5) -0.0062(5) O14 0.0600(8) 0.0970(9) 0.1233(10) -0.0426(8) -0.0305(7) 0.0213(8) C21 0.0509(11) 0.0926(12) 0.0938(11) -0.0571(9) -0.0206(10) 0.0086(10) C21B 0.0350(14) 0.0601(16) 0.0403(12) -0.0224(10) -0.0074(10) -0.0109(12) C20 0.0464(15) 0.1112(18) 0.1037(17) -0.0642(14) -0.0157(14) 0.0133(15) C20B 0.0119(11) 0.1004(17) 0.0564(12) -0.0534(10) 0.0014(9) -0.0088(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O15 C21 1.307(4) . ? O15 Mn3 2.1029(16) 2_577 ? C19 C20 1.293(4) . ? C19 C20B 1.316(3) . ? C19 N9 1.450(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? Mn1 O10 2.1422(13) . ? Mn1 O5 2.1723(12) . ? Mn1 O2W 2.1923(14) . ? Mn1 O4 2.1951(14) 2_477 ? Mn1 N1 2.2255(18) . ? Mn1 O1W 2.2291(15) . ? Mn2 O11 2.0685(14) . ? Mn2 O1 2.1594(14) 1_654 ? Mn2 O6 2.1719(14) 2_577 ? Mn2 N4 2.2505(18) . ? Mn2 O4 2.3030(14) 2_477 ? Mn2 O3 2.3244(12) 2_477 ? Mn3 O2 2.0758(16) . ? Mn3 O15 2.1029(16) 2_577 ? Mn3 O3W 2.1058(16) . ? Mn3 O13 2.144(2) 1_466 ? Mn3 O12 2.245(2) 1_466 ? Mn3 C16 2.546(3) 1_466 ? C1 O1 1.2491(18) . ? C1 O2 1.2616(17) . ? C1 C2 1.490(3) . ? C2 C3 1.514(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N7 1.465(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O3 1.2525(15) . ? C4 O4 1.2517(17) . ? C4 C5 1.4966(19) . ? C5 C6 1.529(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N6 1.465(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O5 1.248(2) . ? C7 O6 1.253(2) . ? C7 C8 1.5295(19) . ? C8 C9 1.498(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N5 1.4741(18) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O8 1.202(3) . ? C10 N7 1.3753(18) . ? C10 N5 1.382(2) . ? C11 O9 1.202(2) . ? C11 N5 1.376(3) . ? C11 N6 1.3937(18) . ? C12 O7 1.2177(18) . ? C12 N6 1.373(2) . ? C12 N7 1.370(3) . ? C13 O11 1.2408(18) . ? C13 O10 1.2575(18) . ? C13 C14 1.510(2) . ? C14 C15 1.515(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N8 1.451(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O13 1.173(3) . ? C16 O12 1.235(3) . ? C16 C17 1.755(5) . ? C16 Mn3 2.546(3) 1_644 ? C17 C18 1.363(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N10 1.671(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C22 O17 1.198(4) . ? C22 N10 1.378(3) . ? C22 N9 1.376(4) . ? C23 O18 1.204(2) . ? C23 N8 1.368(3) . ? C23 N10 1.392(3) . ? C24 O16 1.199(3) . ? C24 N9 1.379(3) . ? C24 N8 1.389(2) . ? C25 N4 1.314(3) . ? C25 N3 1.346(3) . ? C25 H25 0.9300 . ? C26 C28 1.383(3) . ? C26 C27 1.398(3) . ? C26 N4 1.398(2) . ? C27 C31 1.384(3) . ? C27 N3 1.385(2) . ? C28 C29 1.386(3) . ? C28 H28 0.9300 . ? C29 C30 1.391(4) . ? C29 H29 0.9300 . ? C30 C31 1.370(4) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 N3 1.467(3) . ? C32 C33 1.508(2) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.513(2) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.509(2) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 N2 1.480(2) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 N1 1.317(2) . ? C36 N2 1.342(3) . ? C36 H36 0.9300 . ? C37 N2 1.3845(19) . ? C37 C42 1.388(3) . ? C37 C38 1.395(3) . ? C38 N1 1.387(2) . ? C38 C39 1.396(2) . ? C39 C40 1.383(3) . ? C39 H39 0.9300 . ? C40 C41 1.396(3) . ? C40 H40 0.9300 . ? C41 C42 1.376(2) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? O1 Mn2 2.1594(14) 1_456 ? O3 Mn2 2.3244(12) 2_477 ? O4 Mn1 2.1951(14) 2_477 ? O4 Mn2 2.3030(14) 2_477 ? O6 Mn2 2.1719(14) 2_577 ? O12 Mn3 2.245(2) 1_644 ? O13 Mn3 2.144(2) 1_644 ? O1W H1WA 0.8200 . ? O1W H1WB 0.810(18) . ? O2W H2WA 0.8200 . ? O2W H2WB 0.827(8) . ? O3W H3WA 0.8200 . ? O3W H3WB 0.806(16) . ? O14 C21 1.418(4) . ? O14 C21B 1.482(3) . ? C21 C20 1.497(5) . ? C21B C20B 1.514(4) . ? C21B H21A 0.9700 . ? C21B H21B 0.9700 . ? C20B H20A 0.9700 . ? C20B H20B 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 C21 O15 Mn3 120.53(19) . 2_577 ? C20 C19 C20B 131.2(3) . . ? C20 C19 N9 122.0(2) . . ? C20B C19 N9 106.32(19) . . ? C20 C19 H19A 106.8 . . ? C20B C19 H19A 61.1 . . ? N9 C19 H19A 106.8 . . ? C20 C19 H19B 106.8 . . ? C20B C19 H19B 47.6 . . ? N9 C19 H19B 106.8 . . ? H19A C19 H19B 106.7 . . ? O10 Mn1 O5 174.18(5) . . ? O10 Mn1 O2W 84.98(6) . . ? O5 Mn1 O2W 90.16(5) . . ? O10 Mn1 O4 90.12(5) . 2_477 ? O5 Mn1 O4 94.38(5) . 2_477 ? O2W Mn1 O4 172.37(5) . 2_477 ? O10 Mn1 N1 89.98(6) . . ? O5 Mn1 N1 93.48(5) . . ? O2W Mn1 N1 93.11(6) . . ? O4 Mn1 N1 92.73(5) 2_477 . ? O10 Mn1 O1W 88.23(5) . . ? O5 Mn1 O1W 88.31(5) . . ? O2W Mn1 O1W 86.77(6) . . ? O4 Mn1 O1W 87.24(5) 2_477 . ? N1 Mn1 O1W 178.21(4) . . ? O11 Mn2 O1 122.83(5) . 1_654 ? O11 Mn2 O6 88.51(5) . 2_577 ? O1 Mn2 O6 83.74(5) 1_654 2_577 ? O11 Mn2 N4 88.02(6) . . ? O1 Mn2 N4 96.88(5) 1_654 . ? O6 Mn2 N4 176.20(4) 2_577 . ? O11 Mn2 O4 93.54(5) . 2_477 ? O1 Mn2 O4 142.20(5) 1_654 2_477 ? O6 Mn2 O4 87.65(5) 2_577 2_477 ? N4 Mn2 O4 94.09(6) . 2_477 ? O11 Mn2 O3 149.16(4) . 2_477 ? O1 Mn2 O3 87.61(5) 1_654 2_477 ? O6 Mn2 O3 90.26(5) 2_577 2_477 ? N4 Mn2 O3 93.51(6) . 2_477 ? O4 Mn2 O3 55.61(4) 2_477 2_477 ? O2 Mn3 O15 100.01(7) . 2_577 ? O2 Mn3 O3W 107.39(7) . . ? O15 Mn3 O3W 91.13(6) 2_577 . ? O2 Mn3 O13 148.87(6) . 1_466 ? O15 Mn3 O13 99.24(8) 2_577 1_466 ? O3W Mn3 O13 96.43(7) . 1_466 ? O2 Mn3 O12 94.22(8) . 1_466 ? O15 Mn3 O12 108.88(8) 2_577 1_466 ? O3W Mn3 O12 147.64(7) . 1_466 ? O13 Mn3 O12 56.29(7) 1_466 1_466 ? O2 Mn3 C16 122.65(7) . 1_466 ? O15 Mn3 C16 105.73(8) 2_577 1_466 ? O3W Mn3 C16 122.08(7) . 1_466 ? O13 Mn3 C16 27.29(6) 1_466 1_466 ? O12 Mn3 C16 29.00(7) 1_466 1_466 ? O1 C1 O2 121.96(17) . . ? O1 C1 C2 120.82(13) . . ? O2 C1 C2 117.21(14) . . ? C1 C2 C3 113.88(13) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N7 C3 C2 111.27(13) . . ? N7 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? N7 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? O3 C4 O4 119.10(12) . . ? O3 C4 C5 121.68(12) . . ? O4 C4 C5 119.18(11) . . ? C4 C5 C6 115.78(12) . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5B 108.3 . . ? C6 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? N6 C6 C5 112.25(13) . . ? N6 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? N6 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? O5 C7 O6 123.79(12) . . ? O5 C7 C8 116.74(16) . . ? O6 C7 C8 119.46(15) . . ? C9 C8 C7 110.56(11) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N5 C9 C8 112.05(11) . . ? N5 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? N5 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O8 C10 N7 122.04(17) . . ? O8 C10 N5 122.35(13) . . ? N7 C10 N5 115.61(17) . . ? O9 C11 N5 122.36(14) . . ? O9 C11 N6 122.03(18) . . ? N5 C11 N6 115.59(16) . . ? O7 C12 N6 121.31(19) . . ? O7 C12 N7 122.69(18) . . ? N6 C12 N7 115.99(12) . . ? O11 C13 O10 126.55(13) . . ? O11 C13 C14 115.70(14) . . ? O10 C13 C14 117.35(13) . . ? C13 C14 C15 116.39(17) . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14B 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.3 . . ? N8 C15 C14 115.88(13) . . ? N8 C15 H15A 108.3 . . ? C14 C15 H15A 108.3 . . ? N8 C15 H15B 108.3 . . ? C14 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? O13 C16 O12 118.7(3) . . ? O13 C16 C17 114.3(2) . . ? O12 C16 C17 126.2(2) . . ? O13 C16 Mn3 56.88(16) . 1_644 ? O12 C16 Mn3 61.83(16) . 1_644 ? C17 C16 Mn3 168.23(13) . 1_644 ? C18 C17 C16 91.7(3) . . ? C18 C17 H17A 113.3 . . ? C16 C17 H17A 113.3 . . ? C18 C17 H17B 113.3 . . ? C16 C17 H17B 113.3 . . ? H17A C17 H17B 110.7 . . ? C17 C18 N10 90.2(3) . . ? C17 C18 H18A 113.6 . . ? N10 C18 H18A 113.6 . . ? C17 C18 H18B 113.6 . . ? N10 C18 H18B 113.6 . . ? H18A C18 H18B 110.9 . . ? O17 C22 N10 122.9(3) . . ? O17 C22 N9 122.0(2) . . ? N10 C22 N9 115.1(2) . . ? O18 C23 N8 123.5(2) . . ? O18 C23 N10 120.9(3) . . ? N8 C23 N10 115.56(17) . . ? O16 C24 N9 122.05(16) . . ? O16 C24 N8 122.44(19) . . ? N9 C24 N8 115.5(2) . . ? N4 C25 N3 113.89(14) . . ? N4 C25 H25 123.1 . . ? N3 C25 H25 123.1 . . ? C28 C26 C27 120.23(17) . . ? C28 C26 N4 130.5(2) . . ? C27 C26 N4 109.25(16) . . ? C31 C27 C26 122.25(19) . . ? C31 C27 N3 132.3(2) . . ? C26 C27 N3 105.49(15) . . ? C26 C28 C29 117.6(2) . . ? C26 C28 H28 121.2 . . ? C29 C28 H28 121.2 . . ? C28 C29 C30 121.1(2) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 122.0(2) . . ? C31 C30 H30 119.0 . . ? C29 C30 H30 119.0 . . ? C30 C31 C27 116.8(2) . . ? C30 C31 H31 121.6 . . ? C27 C31 H31 121.6 . . ? N3 C32 C33 111.81(15) . . ? N3 C32 H32A 109.3 . . ? C33 C32 H32A 109.3 . . ? N3 C32 H32B 109.3 . . ? C33 C32 H32B 109.3 . . ? H32A C32 H32B 107.9 . . ? C32 C33 C34 114.21(13) . . ? C32 C33 H33A 108.7 . . ? C34 C33 H33A 108.7 . . ? C32 C33 H33B 108.7 . . ? C34 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? C33 C34 C35 113.76(13) . . ? C33 C34 H34A 108.8 . . ? C35 C34 H34A 108.8 . . ? C33 C34 H34B 108.8 . . ? C35 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? N2 C35 C34 111.40(14) . . ? N2 C35 H35A 109.3 . . ? C34 C35 H35A 109.3 . . ? N2 C35 H35B 109.3 . . ? C34 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? N1 C36 N2 113.78(15) . . ? N1 C36 H36 123.1 . . ? N2 C36 H36 123.1 . . ? N2 C37 C42 132.25(17) . . ? N2 C37 C38 105.34(15) . . ? C42 C37 C38 122.41(13) . . ? N1 C38 C37 109.61(13) . . ? N1 C38 C39 130.52(18) . . ? C37 C38 C39 119.88(16) . . ? C40 C39 C38 117.67(18) . . ? C40 C39 H39 121.2 . . ? C38 C39 H39 121.2 . . ? C39 C40 C41 121.66(15) . . ? C39 C40 H40 119.2 . . ? C41 C40 H40 119.2 . . ? C42 C41 C40 121.23(18) . . ? C42 C41 H41 119.4 . . ? C40 C41 H41 119.4 . . ? C41 C42 C37 117.15(18) . . ? C41 C42 H42 121.4 . . ? C37 C42 H42 121.4 . . ? C36 N1 C38 104.60(16) . . ? C36 N1 Mn1 119.99(12) . . ? C38 N1 Mn1 134.91(11) . . ? C36 N2 C37 106.66(14) . . ? C36 N2 C35 125.61(14) . . ? C37 N2 C35 127.60(17) . . ? C25 N3 C27 106.73(17) . . ? C25 N3 C32 125.66(14) . . ? C27 N3 C32 127.31(16) . . ? C25 N4 C26 104.63(16) . . ? C25 N4 Mn2 125.72(11) . . ? C26 N4 Mn2 129.64(14) . . ? C11 N5 C10 124.09(12) . . ? C11 N5 C9 119.12(15) . . ? C10 N5 C9 116.78(16) . . ? C12 N6 C11 123.77(16) . . ? C12 N6 C6 117.54(12) . . ? C11 N6 C6 118.64(15) . . ? C12 N7 C10 124.64(15) . . ? C12 N7 C3 119.01(13) . . ? C10 N7 C3 116.35(16) . . ? C23 N8 C24 124.27(17) . . ? C23 N8 C15 119.77(14) . . ? C24 N8 C15 115.96(18) . . ? C22 N9 C24 124.89(17) . . ? C22 N9 C19 117.9(2) . . ? C24 N9 C19 117.2(2) . . ? C22 N10 C23 124.5(2) . . ? C22 N10 C18 112.7(2) . . ? C23 N10 C18 122.19(18) . . ? C1 O1 Mn2 142.10(14) . 1_456 ? C1 O2 Mn3 106.59(11) . . ? C4 O3 Mn2 92.02(9) . 2_477 ? C4 O4 Mn1 146.33(8) . 2_477 ? C4 O4 Mn2 93.04(8) . 2_477 ? Mn1 O4 Mn2 120.26(6) 2_477 2_477 ? C7 O5 Mn1 133.44(10) . . ? C7 O6 Mn2 136.74(9) . 2_577 ? C13 O10 Mn1 132.63(11) . . ? C13 O11 Mn2 132.25(12) . . ? C16 O12 Mn3 89.16(15) . 1_644 ? C16 O13 Mn3 95.83(17) . 1_644 ? Mn1 O1W H1WA 109.5 . . ? Mn1 O1W H1WB 108.8(17) . . ? H1WA O1W H1WB 124.5 . . ? Mn1 O2W H2WA 109.5 . . ? Mn1 O2W H2WB 112.9(8) . . ? H2WA O2W H2WB 113.5 . . ? Mn3 O3W H3WA 109.5 . . ? Mn3 O3W H3WB 115.7(14) . . ? H3WA O3W H3WB 112.9 . . ? C21 O14 C21B 119.9(2) . . ? O15 C21 O14 128.1(3) . . ? O15 C21 C20 114.8(3) . . ? O14 C21 C20 117.1(3) . . ? O14 C21B C20B 115.9(2) . . ? O14 C21B H21A 108.3 . . ? C20B C21B H21A 108.3 . . ? O14 C21B H21B 108.3 . . ? C20B C21B H21B 108.3 . . ? H21A C21B H21B 107.4 . . ? C19 C20 C21 117.4(3) . . ? C19 C20B C21B 116.3(2) . . ? C19 C20B H20A 108.2 . . ? C21B C20B H20A 108.2 . . ? C19 C20B H20B 108.2 . . ? C21B C20B H20B 108.2 . . ? H20A C20B H20B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.975 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 907896' ####################################################################### # # 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 #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 Mn N5 O9' _chemical_formula_weight 596.46 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 28.334(6) _cell_length_b 13.063(3) _cell_length_c 6.7989(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2516.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7837 _cell_measurement_theta_min 1.5588 _cell_measurement_theta_max 29.1511 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 0.590 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8188 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 ; Saturn724 (4x4 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11500 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4345 _reflns_number_gt 3929 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.3721P] 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 0.02(2) _refine_ls_number_reflns 4345 _refine_ls_number_parameters 362 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.096 _refine_ls_shift/su_mean 0.017 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 0.034244(18) 0.01174(4) 0.08796(10) 0.02446(15) Uani 1 1 d . . . C1 C 0.03430(14) 0.8262(3) -0.1892(6) 0.0274(9) Uani 1 1 d . . . C2 C 0.05443(14) 0.7207(3) -0.2305(6) 0.0336(10) Uani 1 1 d . . . H2A H 0.0864 0.7283 -0.2790 0.040 Uiso 1 1 calc R . . H2B H 0.0559 0.6827 -0.1081 0.040 Uiso 1 1 calc R . . C3 C 0.02615(13) 0.6595(3) -0.3786(7) 0.0337(10) Uani 1 1 d . . . H3A H -0.0028 0.6357 -0.3175 0.040 Uiso 1 1 calc R . . H3B H 0.0177 0.7032 -0.4884 0.040 Uiso 1 1 calc R . . C4 C 0.04463(13) 0.1408(3) -0.2101(6) 0.0261(8) Uani 1 1 d . . . C5 C 0.04431(14) 0.2303(3) -0.3515(6) 0.0277(9) Uani 1 1 d . . . H5A H 0.0138 0.2640 -0.3462 0.033 Uiso 1 1 calc R . . H5B H 0.0490 0.2053 -0.4845 0.033 Uiso 1 1 calc R . . C6 C 0.08300(14) 0.3073(3) -0.3013(6) 0.0319(9) Uani 1 1 d . . . H6A H 0.0808 0.3250 -0.1630 0.038 Uiso 1 1 calc R . . H6B H 0.1136 0.2759 -0.3231 0.038 Uiso 1 1 calc R . . C7 C 0.18119(15) 0.5874(3) -1.1084(7) 0.0381(10) Uani 1 1 d . . . C8 C 0.16690(15) 0.5568(4) -0.9052(7) 0.0488(11) Uani 1 1 d . . . H8A H 0.1909 0.5118 -0.8511 0.059 Uiso 1 1 calc R . . H8B H 0.1655 0.6174 -0.8231 0.059 Uiso 1 1 calc R . . C9 C 0.11994(13) 0.5032(3) -0.8968(8) 0.0346(9) Uani 1 1 d . . . H9A H 0.0979 0.5390 -0.9817 0.042 Uiso 1 1 calc R . . H9B H 0.1236 0.4343 -0.9478 0.042 Uiso 1 1 calc R . . C10 C 0.07620(14) 0.5835(3) -0.6286(6) 0.0317(10) Uani 1 1 d . . . C11 C 0.05203(14) 0.4808(3) -0.3482(6) 0.0292(10) Uani 1 1 d . . . C12 C 0.10490(14) 0.4075(3) -0.5940(6) 0.0304(9) Uani 1 1 d . . . C13 C 0.12483(14) 0.0876(3) 0.3189(7) 0.0364(10) Uani 1 1 d . . . H13 H 0.1237 0.1407 0.2279 0.044 Uiso 1 1 calc R . . C14 C 0.09483(15) -0.0610(4) 0.4419(7) 0.0416(11) Uani 1 1 d . . . H14 H 0.0729 -0.1139 0.4359 0.050 Uiso 1 1 calc R . . C15 C 0.12778(14) -0.0623(3) 0.5898(8) 0.0436(10) Uani 1 1 d . . . H15 H 0.1271 -0.1143 0.6832 0.052 Uiso 1 1 calc R . . C16 C 0.15951(16) 0.0897(3) 0.4612(6) 0.0406(11) Uani 1 1 d . . . H16 H 0.1813 0.1429 0.4630 0.049 Uiso 1 1 calc R . . C17 C 0.16207(13) 0.0129(3) 0.6014(8) 0.0348(9) Uani 1 1 d . . . C18 C 0.2013(2) 0.0087(4) 0.7470(9) 0.0648(17) Uani 1 1 d . . . H18A H 0.2044 0.0762 0.8051 0.078 Uiso 1 1 calc R . . H18B H 0.2303 -0.0048 0.6755 0.078 Uiso 1 1 calc R . . C19 C 0.19812(16) -0.0672(4) 0.9110(7) 0.0427(11) Uani 1 1 d . . . H19A H 0.1713 -0.0497 0.9933 0.051 Uiso 1 1 calc R . . H19B H 0.1923 -0.1344 0.8557 0.051 Uiso 1 1 calc R . . C20 C 0.24149(18) -0.0722(4) 1.0373(7) 0.0612(16) Uani 1 1 d . . . H20A H 0.2481 -0.0037 1.0849 0.073 Uiso 1 1 calc R . . H20B H 0.2678 -0.0923 0.9544 0.073 Uiso 1 1 calc R . . C21 C 0.24037(17) -0.1436(3) 1.2130(6) 0.0411(11) Uani 1 1 d . . . C22 C 0.19996(16) -0.1906(4) 1.2798(7) 0.0444(11) Uani 1 1 d . . . H22 H 0.1716 -0.1813 1.2134 0.053 Uiso 1 1 calc R . . C23 C 0.20159(19) -0.2514(4) 1.4452(7) 0.0499(12) Uani 1 1 d . . . H23 H 0.1736 -0.2815 1.4874 0.060 Uiso 1 1 calc R . . C24 C 0.27949(19) -0.2250(4) 1.4820(7) 0.0523(13) Uani 1 1 d . . . H24 H 0.3074 -0.2362 1.5507 0.063 Uiso 1 1 calc R . . C25 C 0.28098(16) -0.1632(3) 1.3188(7) 0.0436(11) Uani 1 1 d . . . H25 H 0.3095 -0.1345 1.2792 0.052 Uiso 1 1 calc R . . N1 N 0.07954(10) 0.4016(2) -0.4205(6) 0.0291(7) Uani 1 1 d . . . N2 N 0.09980(12) 0.4974(2) -0.6984(5) 0.0309(8) Uani 1 1 d . . . N3 N 0.05318(11) 0.5707(2) -0.4521(5) 0.0274(8) Uani 1 1 d . . . N4 N 0.09278(11) 0.0129(2) 0.3058(5) 0.0298(8) Uani 1 1 d . . . N5 N 0.24015(14) -0.2698(3) 1.5474(6) 0.0478(10) Uani 1 1 d . . . O1 O 0.00030(10) 0.8562(2) -0.2899(5) 0.0383(7) Uani 1 1 d . . . O2 O 0.05450(11) 0.8759(2) -0.0532(4) 0.0355(7) Uani 1 1 d . . . O3 O 0.01081(9) 0.07683(19) -0.2157(4) 0.0306(6) Uani 1 1 d . . . O4 O 0.07646(10) 0.1334(2) -0.0831(4) 0.0365(7) Uani 1 1 d . . . O5 O 0.15819(11) 0.5701(3) -1.2525(5) 0.0508(9) Uani 1 1 d . . . O6 O 0.22156(12) 0.6380(3) -1.1095(5) 0.0565(10) Uani 1 1 d . . . H6 H 0.2266 0.6602 -1.2203 0.085 Uiso 1 1 calc R . . O7 O 0.12971(12) 0.3379(2) -0.6510(5) 0.0524(9) Uani 1 1 d . . . O8 O 0.02912(10) 0.4721(2) -0.1989(5) 0.0430(8) Uani 1 1 d . . . O9 O 0.07689(12) 0.6630(2) -0.7192(5) 0.0528(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0310(3) 0.0195(3) 0.0229(3) 0.0005(3) -0.0001(3) 0.0003(2) C1 0.037(2) 0.021(2) 0.024(2) 0.0032(18) 0.0095(18) 0.0012(17) C2 0.039(2) 0.028(2) 0.034(2) -0.0008(19) -0.005(2) 0.0104(18) C3 0.033(2) 0.029(2) 0.039(3) -0.005(2) 0.0023(19) 0.0094(16) C4 0.032(2) 0.021(2) 0.025(2) -0.0025(16) 0.0028(18) -0.0006(16) C5 0.035(2) 0.0211(19) 0.027(2) 0.0010(15) -0.0035(16) -0.0028(16) C6 0.033(2) 0.023(2) 0.040(2) 0.0061(18) -0.0076(19) -0.0041(17) C7 0.039(2) 0.039(3) 0.037(3) 0.007(2) -0.001(2) 0.003(2) C8 0.046(2) 0.070(3) 0.031(2) 0.000(3) 0.005(3) -0.017(2) C9 0.042(2) 0.036(2) 0.026(2) -0.001(2) 0.003(2) -0.0050(17) C10 0.038(2) 0.024(2) 0.034(2) -0.0018(19) -0.0034(19) 0.0008(18) C11 0.032(2) 0.023(2) 0.033(3) -0.0042(16) -0.0035(17) -0.0075(16) C12 0.034(2) 0.017(2) 0.041(2) -0.0034(18) 0.0025(19) -0.0003(17) C13 0.037(2) 0.028(2) 0.044(3) 0.006(2) -0.009(2) -0.0039(18) C14 0.035(2) 0.045(3) 0.045(3) 0.014(2) -0.008(2) -0.010(2) C15 0.037(2) 0.046(2) 0.049(3) 0.022(3) -0.009(2) -0.0074(18) C16 0.044(3) 0.035(2) 0.043(3) 0.004(2) -0.010(2) -0.007(2) C17 0.0314(18) 0.039(2) 0.034(2) 0.007(2) 0.002(2) 0.0004(16) C18 0.057(3) 0.072(4) 0.065(4) 0.027(3) -0.031(3) -0.023(3) C19 0.042(2) 0.049(3) 0.037(2) 0.002(2) -0.005(2) 0.000(2) C20 0.052(3) 0.075(4) 0.057(4) 0.034(3) -0.019(3) -0.020(3) C21 0.051(3) 0.036(3) 0.036(3) 0.001(2) -0.003(2) -0.003(2) C22 0.042(3) 0.055(3) 0.036(3) 0.005(2) -0.004(2) -0.003(2) C23 0.053(3) 0.055(3) 0.042(3) 0.002(2) 0.006(2) -0.008(2) C24 0.055(3) 0.054(3) 0.048(3) 0.016(2) -0.012(2) -0.006(3) C25 0.038(2) 0.045(3) 0.048(3) 0.012(2) -0.004(2) -0.005(2) N1 0.0327(16) 0.0202(15) 0.0343(18) 0.0022(17) 0.0023(18) -0.0015(12) N2 0.0334(18) 0.0274(19) 0.0318(19) 0.0023(15) 0.0021(16) 0.0017(14) N3 0.0287(16) 0.0223(18) 0.031(2) -0.0038(14) 0.0008(14) 0.0037(13) N4 0.0296(17) 0.0286(18) 0.0312(19) 0.0008(15) -0.0016(15) 0.0005(14) N5 0.060(2) 0.045(2) 0.038(2) 0.0062(19) -0.004(2) -0.0049(19) O1 0.0451(17) 0.0242(15) 0.0456(18) 0.0023(13) -0.0050(14) 0.0121(14) O2 0.0487(18) 0.0262(15) 0.0316(16) -0.0075(13) 0.0012(14) 0.0052(13) O3 0.0389(15) 0.0207(14) 0.0321(15) 0.0018(12) -0.0033(13) -0.0055(12) O4 0.0375(16) 0.0386(17) 0.0335(16) 0.0113(14) -0.0081(14) -0.0085(13) O5 0.0452(18) 0.070(2) 0.0374(19) 0.0085(17) -0.0009(16) -0.0115(17) O6 0.052(2) 0.079(3) 0.0383(19) 0.0126(18) 0.0027(17) -0.0205(19) O7 0.065(2) 0.0308(17) 0.062(2) 0.0019(15) 0.0228(18) 0.0146(16) O8 0.0491(19) 0.0439(19) 0.0359(18) -0.0020(15) 0.0154(15) -0.0042(14) O9 0.074(2) 0.0298(18) 0.055(2) 0.0159(17) 0.0089(19) 0.0089(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 Mn1 O2 2.098(3) 1_545 ? Mn1 O1 2.151(3) 2_565 ? Mn1 O3 2.180(3) 2 ? Mn1 N4 2.224(3) . ? Mn1 O4 2.304(3) . ? Mn1 O3 2.329(3) . ? C1 O1 1.245(5) . ? C1 O2 1.266(5) . ? C1 C2 1.517(5) . ? C2 C3 1.515(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N3 1.477(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O4 1.253(5) . ? C4 O3 1.272(4) . ? C4 C5 1.513(5) . ? C5 C6 1.527(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.479(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O5 1.199(5) . ? C7 O6 1.321(5) . ? C7 C8 1.494(6) . ? C8 C9 1.504(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.467(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O9 1.208(5) . ? C10 N3 1.376(5) . ? C10 N2 1.392(5) . ? C11 O8 1.210(5) . ? C11 N3 1.371(5) . ? C11 N1 1.385(5) . ? C12 O7 1.212(5) . ? C12 N2 1.380(5) . ? C12 N1 1.383(5) . ? C13 N4 1.336(5) . ? C13 C16 1.379(6) . ? C13 H13 0.9300 . ? C14 N4 1.338(5) . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 C17 1.384(5) . ? C15 H15 0.9300 . ? C16 C17 1.386(6) . ? C16 H16 0.9300 . ? C17 C18 1.489(6) . ? C18 C19 1.495(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.500(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.516(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.376(6) . ? C21 C25 1.381(6) . ? C22 C23 1.377(6) . ? C22 H22 0.9300 . ? C23 N5 1.317(6) . ? C23 H23 0.9300 . ? C24 C25 1.372(6) . ? C24 N5 1.335(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? O1 Mn1 2.151(3) 2_564 ? O2 Mn1 2.098(3) 1_565 ? O3 Mn1 2.180(3) 2_554 ? O6 H6 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O1 168.53(12) 1_545 2_565 ? O2 Mn1 O3 89.51(11) 1_545 2 ? O1 Mn1 O3 85.57(11) 2_565 2 ? O2 Mn1 N4 96.10(12) 1_545 . ? O1 Mn1 N4 94.41(12) 2_565 . ? O3 Mn1 N4 91.85(12) 2 . ? O2 Mn1 O4 102.16(12) 1_545 . ? O1 Mn1 O4 82.98(11) 2_565 . ? O3 Mn1 O4 168.33(11) 2 . ? N4 Mn1 O4 86.81(11) . . ? O2 Mn1 O3 88.94(11) 1_545 . ? O1 Mn1 O3 85.39(11) 2_565 . ? O3 Mn1 O3 124.73(6) 2 . ? N4 Mn1 O3 143.18(11) . . ? O4 Mn1 O3 56.56(9) . . ? O1 C1 O2 126.1(4) . . ? O1 C1 C2 118.3(4) . . ? O2 C1 C2 115.5(3) . . ? C3 C2 C1 113.8(3) . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N3 C3 C2 111.4(3) . . ? N3 C3 H3A 109.4 . . ? C2 C3 H3A 109.3 . . ? N3 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? O4 C4 O3 120.8(4) . . ? O4 C4 C5 120.1(3) . . ? O3 C4 C5 119.0(3) . . ? C4 C5 C6 111.2(3) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N1 C6 C5 112.3(3) . . ? N1 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? N1 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? O5 C7 O6 124.1(4) . . ? O5 C7 C8 123.9(4) . . ? O6 C7 C8 112.0(4) . . ? C9 C8 C7 113.5(4) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N2 C9 C8 113.8(4) . . ? N2 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? N2 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? O9 C10 N3 123.9(4) . . ? O9 C10 N2 120.9(4) . . ? N3 C10 N2 115.3(3) . . ? O8 C11 N3 121.7(4) . . ? O8 C11 N1 122.0(4) . . ? N3 C11 N1 116.3(4) . . ? O7 C12 N2 122.3(4) . . ? O7 C12 N1 122.2(4) . . ? N2 C12 N1 115.5(3) . . ? N4 C13 C16 123.1(4) . . ? N4 C13 H13 118.5 . . ? C16 C13 H13 118.5 . . ? N4 C14 C15 123.1(4) . . ? N4 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C17 C15 C14 120.7(4) . . ? C17 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C13 C16 C17 120.4(4) . . ? C13 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C15 C17 C16 116.0(4) . . ? C15 C17 C18 122.4(4) . . ? C16 C17 C18 121.5(4) . . ? C17 C18 C19 118.4(4) . . ? C17 C18 H18A 107.7 . . ? C19 C18 H18A 107.7 . . ? C17 C18 H18B 107.7 . . ? C19 C18 H18B 107.7 . . ? H18A C18 H18B 107.1 . . ? C20 C19 C18 114.0(4) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 117.5(4) . . ? C19 C20 H20A 107.9 . . ? C21 C20 H20A 107.9 . . ? C19 C20 H20B 107.9 . . ? C21 C20 H20B 107.9 . . ? H20A C20 H20B 107.2 . . ? C22 C21 C25 116.0(4) . . ? C22 C21 C20 123.5(4) . . ? C25 C21 C20 120.5(4) . . ? C21 C22 C23 119.9(5) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? N5 C23 C22 124.3(5) . . ? N5 C23 H23 117.8 . . ? C22 C23 H23 117.9 . . ? C25 C24 N5 123.5(5) . . ? C25 C24 H24 118.2 . . ? N5 C24 H24 118.2 . . ? C24 C25 C21 120.3(5) . . ? C24 C25 H25 119.8 . . ? C21 C25 H25 119.8 . . ? C12 N1 C11 123.6(3) . . ? C12 N1 C6 118.6(3) . . ? C11 N1 C6 117.7(4) . . ? C12 N2 C10 124.2(4) . . ? C12 N2 C9 118.5(3) . . ? C10 N2 C9 117.3(3) . . ? C11 N3 C10 124.4(3) . . ? C11 N3 C3 119.1(3) . . ? C10 N3 C3 116.4(3) . . ? C13 N4 C14 116.8(4) . . ? C13 N4 Mn1 123.8(3) . . ? C14 N4 Mn1 119.2(3) . . ? C23 N5 C24 115.9(4) . . ? C1 O1 Mn1 144.8(3) . 2_564 ? C1 O2 Mn1 130.1(3) . 1_565 ? C4 O3 Mn1 143.9(3) . 2_554 ? C4 O3 Mn1 89.9(2) . . ? Mn1 O3 Mn1 121.07(11) 2_554 . ? C4 O4 Mn1 91.6(2) . . ? C7 O6 H6 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.329 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 907897'