# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name L.Jones E.Brechin _publ_contact_author_name 'Leigh Jones' _publ_contact_author_email leigh.jones@nuigalway.ie data_eh68c-1 _database_code_depnum_ccdc_archive 'CCDC 873519' #TrackingRef '- Mn2(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Mn2(Napth-sao)2(Napth-saoH)2(MeOH)2].4MeOH' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H54 Mn2 N4 O14' _chemical_formula_weight 1044.85 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4931(17) _cell_length_b 22.495(5) _cell_length_c 24.783(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4734.9(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 0.607 _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 2.9018 _cell_measurement_reflns_used 6049 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_T_min 0.96949 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 14243 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.9018 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 0.0095699000 _diffrn_orient_matrix_UB_12 0.0179696000 _diffrn_orient_matrix_UB_13 0.0232819000 _diffrn_orient_matrix_UB_21 -0.0828823000 _diffrn_orient_matrix_UB_22 0.0032194000 _diffrn_orient_matrix_UB_23 0.0019555000 _diffrn_orient_matrix_UB_31 -0.0037045000 _diffrn_orient_matrix_UB_32 -0.0257099000 _diffrn_orient_matrix_UB_33 0.0165285000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 67.00 93.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 18.6403 179.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -53.00 63.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 18.6403 0.0000 150.0000 116 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(2) _reflns_number_total 4330 _reflns_number_gt 3682 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0409P)^2^+3.5946P] 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 4330 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.98165(4) 0.010899(15) 0.080358(14) 0.01808(12) Uani 1 1 d . . . O1 O 1.14669(19) 0.06308(7) 0.09962(7) 0.0210(4) Uani 1 1 d . . . O2 O 0.86384(18) 0.03876(6) -0.02537(6) 0.0188(3) Uani 1 1 d . . . O3 O 1.0331(2) -0.03351(7) 0.14230(7) 0.0241(4) Uani 1 1 d . . . O4 O 0.6977(2) -0.03909(8) 0.02509(7) 0.0278(4) Uani 1 1 d . . . H4 H 0.7293 -0.0112 0.0053 0.033 Uiso 1 1 calc R . . O5 O 0.8011(2) 0.06347(9) 0.12519(8) 0.0327(4) Uani 1 1 d . . . O6 O 1.3510(3) 0.00276(11) 0.17795(9) 0.0464(6) Uani 1 1 d . . . O7 O 0.8561(3) 0.06559(10) 0.23058(8) 0.0421(5) Uani 1 1 d . . . N1 N 0.9362(2) 0.06448(8) 0.01828(7) 0.0170(4) Uani 1 1 d . . . N2 N 0.8085(2) -0.04989(8) 0.06540(8) 0.0194(4) Uani 1 1 d . . . C1 C 1.1529(3) 0.12150(10) 0.09311(9) 0.0186(5) Uani 1 1 d . . . C2 C 1.2516(3) 0.15384(10) 0.12949(9) 0.0219(5) Uani 1 1 d . . . H2 H 1.3083 0.1330 0.1566 0.026 Uiso 1 1 calc R . . C3 C 1.2653(3) 0.21389(11) 0.12589(10) 0.0238(5) Uani 1 1 d . . . H3 H 1.3317 0.2343 0.1506 0.029 Uiso 1 1 calc R . . C4 C 1.1823(3) 0.24684(10) 0.08592(9) 0.0210(5) Uani 1 1 d . . . C5 C 1.1945(3) 0.30954(10) 0.08247(10) 0.0263(6) Uani 1 1 d . . . H5 H 1.2584 0.3302 0.1077 0.032 Uiso 1 1 calc R . . C6 C 1.1164(3) 0.34078(10) 0.04358(10) 0.0262(6) Uani 1 1 d . . . H6 H 1.1270 0.3828 0.0415 0.031 Uiso 1 1 calc R . . C7 C 1.0204(3) 0.31055(11) 0.00674(10) 0.0262(6) Uani 1 1 d . . . H7 H 0.9656 0.3322 -0.0203 0.031 Uiso 1 1 calc R . . C8 C 1.0045(3) 0.24972(11) 0.00928(10) 0.0233(5) Uani 1 1 d . . . H8 H 0.9378 0.2301 -0.0158 0.028 Uiso 1 1 calc R . . C9 C 1.0858(3) 0.21571(9) 0.04860(9) 0.0185(5) Uani 1 1 d . . . C10 C 1.0712(3) 0.15165(10) 0.05267(9) 0.0184(5) Uani 1 1 d . . . C11 C 0.9808(3) 0.11934(9) 0.01316(9) 0.0172(5) Uani 1 1 d . . . H11 H 0.9519 0.1397 -0.0189 0.021 Uiso 1 1 calc R . . C12 C 0.7821(3) -0.09876(10) 0.09092(9) 0.0203(5) Uani 1 1 d . . . H12 H 0.6971 -0.1226 0.0786 0.024 Uiso 1 1 calc R . . C13 C 0.8703(3) -0.12050(10) 0.13668(9) 0.0196(5) Uani 1 1 d . . . C14 C 0.8325(3) -0.17794(10) 0.15927(10) 0.0204(5) Uani 1 1 d . . . C15 C 0.7214(3) -0.21780(10) 0.13641(10) 0.0252(5) Uani 1 1 d . . . H15 H 0.6691 -0.2071 0.1039 0.030 Uiso 1 1 calc R . . C16 C 0.6878(3) -0.27122(11) 0.16015(11) 0.0307(6) Uani 1 1 d . . . H16 H 0.6132 -0.2970 0.1438 0.037 Uiso 1 1 calc R . . C17 C 0.7619(3) -0.28847(11) 0.20830(11) 0.0313(6) Uani 1 1 d . . . H17 H 0.7362 -0.3253 0.2248 0.038 Uiso 1 1 calc R . . C18 C 0.8710(3) -0.25184(11) 0.23115(11) 0.0289(6) Uani 1 1 d . . . H18 H 0.9224 -0.2637 0.2635 0.035 Uiso 1 1 calc R . . C19 C 0.9090(3) -0.19632(10) 0.20741(10) 0.0224(5) Uani 1 1 d . . . C20 C 1.0245(3) -0.15885(11) 0.23104(10) 0.0256(5) Uani 1 1 d . . . H20 H 1.0755 -0.1711 0.2633 0.031 Uiso 1 1 calc R . . C21 C 1.0636(3) -0.10594(11) 0.20850(10) 0.0238(5) Uani 1 1 d . . . H21 H 1.1426 -0.0821 0.2249 0.029 Uiso 1 1 calc R . . C22 C 0.9879(3) -0.08552(10) 0.16060(9) 0.0195(5) Uani 1 1 d . . . C23 C 0.6590(3) 0.08985(13) 0.10646(11) 0.0350(6) Uani 1 1 d . . . H23A H 0.6331 0.0740 0.0707 0.052 Uiso 1 1 calc R . . H23B H 0.6725 0.1330 0.1041 0.052 Uiso 1 1 calc R . . H23C H 0.5734 0.0807 0.1316 0.052 Uiso 1 1 calc R . . C24 C 1.4424(4) -0.04192(14) 0.15381(13) 0.0471(8) Uani 1 1 d . . . H24A H 1.5484 -0.0416 0.1695 0.071 Uiso 1 1 calc R . . H24B H 1.4494 -0.0346 0.1149 0.071 Uiso 1 1 calc R . . H24C H 1.3933 -0.0807 0.1602 0.071 Uiso 1 1 calc R . . C25 C 1.0127(4) 0.08314(15) 0.23414(12) 0.0449(8) Uani 1 1 d . . . H25A H 1.0337 0.1142 0.2073 0.067 Uiso 1 1 calc R . . H25B H 1.0811 0.0489 0.2272 0.067 Uiso 1 1 calc R . . H25C H 1.0336 0.0987 0.2704 0.067 Uiso 1 1 calc R . . H1 H 0.806(4) 0.0614(14) 0.1597(14) 0.049(10) Uiso 1 1 d . . . H7H H 0.839(5) 0.0359(16) 0.2569(16) 0.074(12) Uiso 1 1 d . . . H6H H 1.282(5) 0.0068(19) 0.1623(17) 0.079(16) 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 0.0223(2) 0.01523(19) 0.01673(19) 0.00134(14) -0.00361(15) -0.00153(14) O1 0.0236(9) 0.0164(8) 0.0230(8) 0.0012(7) -0.0047(7) -0.0010(7) O2 0.0239(8) 0.0162(7) 0.0164(8) -0.0030(7) -0.0060(7) -0.0003(6) O3 0.0310(9) 0.0214(8) 0.0201(8) 0.0043(7) -0.0065(7) -0.0063(7) O4 0.0270(9) 0.0289(9) 0.0274(9) 0.0120(8) -0.0105(8) -0.0074(7) O5 0.0327(10) 0.0439(11) 0.0216(9) -0.0006(9) -0.0003(8) 0.0126(8) O6 0.0343(12) 0.0644(15) 0.0407(12) -0.0274(11) -0.0126(11) 0.0151(11) O7 0.0469(13) 0.0509(13) 0.0284(10) 0.0089(10) -0.0003(9) 0.0026(10) N1 0.0195(10) 0.0153(9) 0.0161(9) -0.0027(8) -0.0025(8) 0.0015(8) N2 0.0215(10) 0.0197(10) 0.0170(9) 0.0017(8) -0.0036(8) -0.0009(8) C1 0.0187(11) 0.0184(11) 0.0188(11) -0.0019(10) 0.0041(9) -0.0005(9) C2 0.0220(12) 0.0240(12) 0.0197(12) -0.0016(10) -0.0030(10) 0.0001(10) C3 0.0218(12) 0.0271(12) 0.0227(12) -0.0061(11) 0.0007(10) -0.0058(10) C4 0.0207(11) 0.0200(11) 0.0222(12) -0.0033(10) 0.0061(10) -0.0024(9) C5 0.0256(13) 0.0225(12) 0.0308(13) -0.0084(11) 0.0060(11) -0.0070(10) C6 0.0293(13) 0.0156(11) 0.0338(14) -0.0016(11) 0.0097(12) -0.0025(10) C7 0.0316(14) 0.0187(11) 0.0282(13) 0.0038(11) 0.0042(11) 0.0003(10) C8 0.0280(13) 0.0178(11) 0.0242(13) -0.0013(10) -0.0003(11) -0.0024(10) C9 0.0184(11) 0.0163(11) 0.0207(11) -0.0020(9) 0.0070(10) -0.0011(9) C10 0.0196(11) 0.0172(11) 0.0184(11) -0.0009(10) 0.0023(10) -0.0001(9) C11 0.0204(11) 0.0138(10) 0.0174(11) 0.0013(9) 0.0003(9) 0.0034(9) C12 0.0204(12) 0.0192(11) 0.0213(12) -0.0010(10) 0.0001(10) -0.0016(9) C13 0.0203(12) 0.0203(11) 0.0182(11) -0.0009(10) 0.0010(10) 0.0010(9) C14 0.0188(11) 0.0202(11) 0.0221(12) 0.0014(10) 0.0030(10) 0.0031(9) C15 0.0286(13) 0.0216(12) 0.0256(13) 0.0027(11) -0.0021(11) -0.0023(10) C16 0.0330(14) 0.0209(12) 0.0382(15) 0.0009(12) -0.0055(13) -0.0050(11) C17 0.0334(14) 0.0229(13) 0.0376(15) 0.0089(12) -0.0020(13) -0.0027(11) C18 0.0293(13) 0.0264(12) 0.0310(14) 0.0103(11) -0.0026(11) 0.0026(11) C19 0.0234(12) 0.0218(12) 0.0220(12) 0.0015(10) 0.0013(10) 0.0029(10) C20 0.0265(13) 0.0283(13) 0.0221(12) 0.0063(11) -0.0046(10) 0.0020(10) C21 0.0256(12) 0.0270(13) 0.0190(11) -0.0005(10) -0.0042(10) -0.0038(10) C22 0.0235(12) 0.0172(11) 0.0178(11) 0.0020(10) 0.0018(10) -0.0006(9) C23 0.0317(15) 0.0408(16) 0.0325(15) -0.0008(13) -0.0001(12) 0.0078(12) C24 0.0513(19) 0.0446(18) 0.0453(18) -0.0097(15) 0.0087(16) 0.0050(15) C25 0.052(2) 0.0534(19) 0.0294(15) 0.0008(14) 0.0037(14) -0.0060(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 1.8829(16) . ? Mn1 O1 1.8896(16) . ? Mn1 N1 1.9922(19) . ? Mn1 N2 2.0423(19) . ? Mn1 O2 2.1970(16) 5_755 ? Mn1 O5 2.2323(18) . ? O1 C1 1.325(3) . ? O2 N1 1.372(2) . ? O2 Mn1 2.1970(16) 5_755 ? O3 C22 1.312(3) . ? O4 N2 1.393(2) . ? O4 H4 0.8400 . ? O5 C23 1.423(3) . ? O5 H1 0.86(3) . ? O6 C24 1.404(4) . ? O6 H6H 0.71(4) . ? O7 C25 1.390(4) . ? O7 H7H 0.94(4) . ? N1 C11 1.297(3) . ? N2 C12 1.288(3) . ? C1 C10 1.395(3) . ? C1 C2 1.430(3) . ? C2 C3 1.359(3) . ? C2 H2 0.9500 . ? C3 C4 1.424(3) . ? C3 H3 0.9500 . ? C4 C9 1.420(3) . ? C4 C5 1.417(3) . ? C5 C6 1.365(4) . ? C5 H5 0.9500 . ? C6 C7 1.400(4) . ? C6 H6 0.9500 . ? C7 C8 1.376(3) . ? C7 H7 0.9500 . ? C8 C9 1.418(3) . ? C8 H8 0.9500 . ? C9 C10 1.450(3) . ? C10 C11 1.441(3) . ? C11 H11 0.9500 . ? C12 C13 1.445(3) . ? C12 H12 0.9500 . ? C13 C22 1.403(3) . ? C13 C14 1.444(3) . ? C14 C15 1.420(3) . ? C14 C19 1.420(3) . ? C15 C16 1.368(3) . ? C15 H15 0.9500 . ? C16 C17 1.404(4) . ? C16 H16 0.9500 . ? C17 C18 1.363(4) . ? C17 H17 0.9500 . ? C18 C19 1.418(3) . ? C18 H18 0.9500 . ? C19 C20 1.420(3) . ? C20 C21 1.356(3) . ? C20 H20 0.9500 . ? C21 C22 1.426(3) . ? C21 H21 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O1 87.22(7) . . ? O3 Mn1 N1 174.61(7) . . ? O1 Mn1 N1 87.88(7) . . ? O3 Mn1 N2 87.70(7) . . ? O1 Mn1 N2 174.92(7) . . ? N1 Mn1 N2 97.20(8) . . ? O3 Mn1 O2 95.59(7) . 5_755 ? O1 Mn1 O2 91.69(7) . 5_755 ? N1 Mn1 O2 86.81(7) . 5_755 ? N2 Mn1 O2 88.69(7) . 5_755 ? O3 Mn1 O5 91.98(7) . . ? O1 Mn1 O5 93.13(7) . . ? N1 Mn1 O5 86.04(7) . . ? N2 Mn1 O5 87.15(8) . . ? O2 Mn1 O5 171.22(6) 5_755 . ? C1 O1 Mn1 127.94(15) . . ? N1 O2 Mn1 115.84(12) . 5_755 ? C22 O3 Mn1 133.39(15) . . ? N2 O4 H4 109.5 . . ? C23 O5 Mn1 129.88(16) . . ? C23 O5 H1 113(2) . . ? Mn1 O5 H1 116(2) . . ? C24 O6 H6H 108(4) . . ? C25 O7 H7H 108(2) . . ? C11 N1 O2 117.05(18) . . ? C11 N1 Mn1 126.48(16) . . ? O2 N1 Mn1 116.14(12) . . ? C12 N2 O4 112.55(18) . . ? C12 N2 Mn1 127.42(16) . . ? O4 N2 Mn1 119.97(13) . . ? O1 C1 C10 123.4(2) . . ? O1 C1 C2 116.8(2) . . ? C10 C1 C2 119.8(2) . . ? C3 C2 C1 121.0(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C9 C4 C5 119.6(2) . . ? C9 C4 C3 118.8(2) . . ? C5 C4 C3 121.6(2) . . ? C6 C5 C4 121.3(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.3(2) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 117.5(2) . . ? C8 C9 C10 122.8(2) . . ? C4 C9 C10 119.6(2) . . ? C1 C10 C11 120.52(19) . . ? C1 C10 C9 119.4(2) . . ? C11 C10 C9 120.0(2) . . ? N1 C11 C10 124.7(2) . . ? N1 C11 H11 117.7 . . ? C10 C11 H11 117.7 . . ? N2 C12 C13 125.7(2) . . ? N2 C12 H12 117.1 . . ? C13 C12 H12 117.1 . . ? C22 C13 C14 119.7(2) . . ? C22 C13 C12 120.7(2) . . ? C14 C13 C12 119.5(2) . . ? C15 C14 C19 117.1(2) . . ? C15 C14 C13 123.9(2) . . ? C19 C14 C13 119.0(2) . . ? C16 C15 C14 121.4(2) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 121.0(2) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 119.4(2) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 121.0(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C14 120.1(2) . . ? C18 C19 C20 120.6(2) . . ? C14 C19 C20 119.3(2) . . ? C21 C20 C19 121.4(2) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 121.0(2) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? O3 C22 C13 124.2(2) . . ? O3 C22 C21 116.3(2) . . ? C13 C22 C21 119.5(2) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O7 C25 H25A 109.5 . . ? O7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.287 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.057