# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Leigh Jones' _publ_contact_author_email LEIGH.JONES@NUIGALWAY.IE _publ_section_title ; A F-bridged Mn(II) Molecular Square ; loop_ _publ_author_name 'Leigh Jones' 'Euan Brechin' 'Kevin Mason' 'Sean Meally' 'Alan G. Ryder' # Attachment 'Mn4-cif.cif' data_lfj39b-3 _database_code_depnum_ccdc_archive 'CCDC 743466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Mn4F4(1,10-phen)8(NO3)4.12(H2O) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C96 H88 F4 Mn4 N20 O24' _chemical_formula_weight 2201.62 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' F F 0.0171 0.0103 '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 Tetragonal _symmetry_space_group_name_H-M I41/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 26.912(4) _cell_length_b 26.912(4) _cell_length_c 13.231(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9583(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4432 _exptl_absorpt_coefficient_mu 0.610 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _exptl_absorpt_correction_T_min 0.90845 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) 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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 11060 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.1063 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.7432 _diffrn_reflns_theta_max 25.34 _diffrn_orient_matrix_UB_11 0.0131808566 _diffrn_orient_matrix_UB_12 0.0069492865 _diffrn_orient_matrix_UB_13 0.0443354411 _diffrn_orient_matrix_UB_21 -0.0226501308 _diffrn_orient_matrix_UB_22 0.0075863207 _diffrn_orient_matrix_UB_23 0.0229144593 _diffrn_orient_matrix_UB_31 -0.0032871780 _diffrn_orient_matrix_UB_32 -0.0243301878 _diffrn_orient_matrix_UB_33 0.0198182317 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 38.00 84.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 19.7341 37.0000 -120.0000 46 #__ type_ start__ end____ width___ exp.time_ 2 omega -8.00 73.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 19.7341 -119.0000 -162.0000 81 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(2) _reflns_number_total 4188 _reflns_number_gt 2486 _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^)+(0.0951P)^2^+42.0105P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4188 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.2268 _refine_ls_wR_factor_gt 0.2105 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.59124(4) 0.72042(4) 0.65244(8) 0.0233(3) Uani 1 1 d . . . F1 F 0.52349(14) 0.68915(15) 0.6874(3) 0.0332(10) Uani 1 1 d . . . N2 N 0.6229(2) 0.6442(2) 0.6977(4) 0.0236(13) Uani 1 1 d . . . N3 N 0.6659(2) 0.7658(2) 0.6690(4) 0.0246(14) Uani 1 1 d . . . C6 C 0.6462(2) 0.6191(2) 0.6236(6) 0.0256(16) Uani 1 1 d . . . N4 N 0.5969(2) 0.7476(2) 0.8152(5) 0.0274(14) Uani 1 1 d . . . C13 C 0.6981(3) 0.7754(3) 0.5986(6) 0.0286(17) Uani 1 1 d . . . H13 H 0.6923 0.7629 0.5325 0.034 Uiso 1 1 calc R . . N1 N 0.6233(2) 0.6840(2) 0.5109(4) 0.0282(14) Uani 1 1 d . . . C10 C 0.6697(2) 0.5725(3) 0.6421(6) 0.0301(18) Uani 1 1 d . . . C18 C 0.6386(3) 0.7738(3) 0.8399(5) 0.0280(17) Uani 1 1 d . . . C16 C 0.7155(2) 0.8126(2) 0.7883(6) 0.0261(17) Uani 1 1 d . . . C5 C 0.6478(2) 0.6400(3) 0.5237(5) 0.0263(17) Uani 1 1 d . . . C8 C 0.6409(3) 0.5764(3) 0.8113(6) 0.0349(19) Uani 1 1 d . . . H8 H 0.6377 0.5621 0.8766 0.042 Uiso 1 1 calc R . . C15 C 0.7496(3) 0.8227(3) 0.7087(6) 0.0360(19) Uani 1 1 d . . . H15 H 0.7780 0.8428 0.7210 0.043 Uiso 1 1 calc R . . C2 C 0.6485(3) 0.6827(3) 0.3358(6) 0.043(2) Uani 1 1 d . . . H2 H 0.6483 0.6984 0.2715 0.051 Uiso 1 1 calc R . . C12 C 0.6970(3) 0.5698(3) 0.4672(6) 0.037(2) Uani 1 1 d . . . H12 H 0.7150 0.5539 0.4145 0.045 Uiso 1 1 calc R . . C9 C 0.6658(3) 0.5527(3) 0.7372(6) 0.0341(19) Uani 1 1 d . . . H9 H 0.6810 0.5216 0.7512 0.041 Uiso 1 1 calc R . . C24 C 0.7220(3) 0.8305(3) 0.8881(6) 0.0340(19) Uani 1 1 d . . . H24 H 0.7502 0.8505 0.9028 0.041 Uiso 1 1 calc R . . C14 C 0.7417(3) 0.8038(3) 0.6166(6) 0.0302(17) Uani 1 1 d . . . H14 H 0.7650 0.8093 0.5638 0.036 Uiso 1 1 calc R . . C17 C 0.6734(3) 0.7845(2) 0.7643(5) 0.0249(16) Uani 1 1 d . . . C1 C 0.6242(3) 0.7037(3) 0.4192(6) 0.0359(19) Uani 1 1 d . . . H1 H 0.6071 0.7341 0.4092 0.043 Uiso 1 1 calc R . . C7 C 0.6197(3) 0.6229(3) 0.7893(6) 0.0324(18) Uani 1 1 d . . . H7 H 0.6024 0.6400 0.8414 0.039 Uiso 1 1 calc R . . C11 C 0.6957(3) 0.5490(3) 0.5594(6) 0.0338(19) Uani 1 1 d . . . H11 H 0.7123 0.5183 0.5705 0.041 Uiso 1 1 calc R . . C4 C 0.6714(3) 0.6158(3) 0.4472(6) 0.0319(18) Uani 1 1 d . . . C23 C 0.6905(3) 0.8205(3) 0.9606(6) 0.0360(19) Uani 1 1 d . . . H23 H 0.6965 0.8327 1.0268 0.043 Uiso 1 1 calc R . . C21 C 0.6113(3) 0.7785(3) 1.0148(7) 0.050(2) Uani 1 1 d . . . H21 H 0.6153 0.7897 1.0824 0.060 Uiso 1 1 calc R . . C22 C 0.6461(3) 0.7907(3) 0.9407(6) 0.0329(18) Uani 1 1 d . . . C3 C 0.6726(3) 0.6384(3) 0.3515(6) 0.0367(19) Uani 1 1 d . . . H3 H 0.6902 0.6230 0.2976 0.044 Uiso 1 1 calc R . . C19 C 0.5644(3) 0.7360(3) 0.8865(6) 0.040(2) Uani 1 1 d . . . H19 H 0.5357 0.7175 0.8686 0.048 Uiso 1 1 calc R . . C20 C 0.5713(3) 0.7502(4) 0.9885(6) 0.049(2) Uani 1 1 d . . . H20 H 0.5481 0.7401 1.0386 0.059 Uiso 1 1 calc R . . O1 O 0.7033(2) 0.6208(3) 0.1039(5) 0.0575(17) Uani 1 1 d . . . N5 N 0.6583(3) 0.6142(4) 0.0785(6) 0.060(2) Uani 1 1 d . . . O2 O 0.6410(3) 0.5710(3) 0.0714(5) 0.073(2) Uani 1 1 d . . . O3 O 0.6309(3) 0.6508(3) 0.0616(8) 0.114(3) Uani 1 1 d . . . O16 O 0.7618(3) 0.7803(3) 0.3727(5) 0.072(2) Uani 1 1 d . . . O17 O 0.6817(3) 0.7887(2) 0.2449(6) 0.084(2) Uani 1 1 d . . . O15 O 0.7462(3) 0.9534(3) 0.2752(6) 0.087(2) 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 0.0190(6) 0.0193(6) 0.0316(6) -0.0019(5) -0.0013(5) 0.0002(5) F1 0.024(2) 0.038(2) 0.038(3) 0.004(2) -0.0025(19) -0.0042(19) N2 0.019(3) 0.027(3) 0.025(3) -0.006(3) -0.001(3) -0.004(3) N3 0.023(3) 0.020(3) 0.031(4) -0.003(3) -0.004(3) 0.004(2) C6 0.019(3) 0.022(4) 0.035(4) -0.001(3) -0.005(3) -0.005(3) N4 0.022(3) 0.028(3) 0.033(4) -0.006(3) 0.000(3) 0.000(3) C13 0.031(4) 0.028(4) 0.027(4) -0.005(3) 0.001(4) 0.000(3) N1 0.032(3) 0.017(3) 0.035(4) -0.001(3) 0.004(3) -0.001(3) C10 0.016(3) 0.031(4) 0.043(5) -0.001(4) -0.009(3) -0.009(3) C18 0.033(4) 0.022(4) 0.029(4) -0.004(3) -0.006(3) 0.005(3) C16 0.020(4) 0.019(3) 0.039(5) -0.003(3) -0.003(3) 0.001(3) C5 0.019(3) 0.030(4) 0.030(4) -0.004(3) 0.000(3) -0.005(3) C8 0.034(4) 0.036(4) 0.035(5) 0.008(4) 0.005(4) 0.000(4) C15 0.026(4) 0.025(4) 0.057(6) 0.003(4) -0.003(4) 0.002(3) C2 0.059(6) 0.043(5) 0.026(5) -0.005(4) -0.003(4) -0.001(4) C12 0.031(4) 0.037(4) 0.043(5) -0.017(4) 0.001(4) 0.007(4) C9 0.028(4) 0.031(4) 0.044(5) 0.005(4) -0.008(4) -0.002(3) C24 0.034(4) 0.026(4) 0.042(5) -0.004(4) -0.012(4) -0.001(4) C14 0.029(4) 0.031(4) 0.031(4) 0.002(3) 0.004(3) -0.001(3) C17 0.030(4) 0.018(3) 0.027(4) -0.003(3) 0.000(3) 0.008(3) C1 0.043(5) 0.036(4) 0.029(5) -0.003(4) 0.000(4) 0.002(4) C7 0.026(4) 0.035(4) 0.037(5) 0.001(4) 0.004(3) -0.006(3) C11 0.031(4) 0.019(4) 0.051(6) -0.009(4) -0.004(4) 0.006(3) C4 0.035(4) 0.025(4) 0.036(5) -0.010(4) -0.003(4) -0.001(3) C23 0.043(5) 0.038(4) 0.027(4) -0.003(4) -0.003(4) -0.004(4) C21 0.054(6) 0.064(6) 0.032(5) -0.009(4) -0.003(4) 0.000(5) C22 0.033(4) 0.040(4) 0.025(4) -0.002(4) -0.005(4) 0.002(4) C3 0.041(5) 0.040(5) 0.029(4) -0.008(4) 0.006(4) 0.001(4) C19 0.042(5) 0.043(5) 0.035(5) -0.015(4) 0.005(4) -0.005(4) C20 0.038(5) 0.070(6) 0.038(5) -0.010(5) 0.006(4) -0.014(5) O1 0.039(4) 0.074(5) 0.059(4) -0.007(4) 0.000(3) -0.001(3) N5 0.070(6) 0.071(6) 0.039(5) -0.008(4) 0.001(4) 0.000(5) O2 0.093(6) 0.074(5) 0.053(4) -0.004(4) 0.015(4) -0.030(4) O3 0.098(7) 0.088(6) 0.156(9) 0.000(6) -0.042(6) 0.032(5) O16 0.104(6) 0.068(5) 0.042(4) -0.006(3) 0.001(4) -0.012(4) O17 0.126(7) 0.049(4) 0.078(5) 0.001(4) -0.035(5) -0.009(4) O15 0.096(6) 0.059(5) 0.107(6) 0.012(4) 0.030(5) 0.002(4) _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 F1 2.030(4) 16_656 ? Mn1 F1 2.061(4) . ? Mn1 N4 2.280(6) . ? Mn1 N1 2.283(6) . ? Mn1 N2 2.301(6) . ? Mn1 N3 2.361(6) . ? F1 Mn1 2.030(4) 14_566 ? N2 C7 1.343(9) . ? N2 C6 1.345(9) . ? N3 C13 1.299(9) . ? N3 C17 1.373(9) . ? C6 C10 1.427(10) . ? C6 C5 1.435(10) . ? N4 C19 1.323(9) . ? N4 C18 1.363(9) . ? C13 C14 1.421(10) . ? C13 H13 0.9500 . ? N1 C1 1.323(9) . ? N1 C5 1.366(9) . ? C10 C9 1.369(11) . ? C10 C11 1.445(11) . ? C18 C17 1.401(10) . ? C18 C22 1.423(10) . ? C16 C17 1.398(9) . ? C16 C24 1.416(10) . ? C16 C15 1.423(10) . ? C5 C4 1.362(10) . ? C8 C9 1.349(11) . ? C8 C7 1.405(10) . ? C8 H8 0.9500 . ? C15 C14 1.338(11) . ? C15 H15 0.9500 . ? C2 C3 1.375(11) . ? C2 C1 1.401(11) . ? C2 H2 0.9500 . ? C12 C11 1.342(11) . ? C12 C4 1.443(10) . ? C12 H12 0.9500 . ? C9 H9 0.9500 . ? C24 C23 1.308(11) . ? C24 H24 0.9500 . ? C14 H14 0.9500 . ? C1 H1 0.9500 . ? C7 H7 0.9500 . ? C11 H11 0.9500 . ? C4 C3 1.404(11) . ? C23 C22 1.463(10) . ? C23 H23 0.9500 . ? C21 C20 1.362(11) . ? C21 C22 1.396(11) . ? C21 H21 0.9500 . ? C3 H3 0.9500 . ? C19 C20 1.416(11) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? O1 N5 1.270(10) . ? N5 O3 1.251(11) . ? N5 O2 1.255(10) . ? 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 F1 Mn1 F1 93.6(2) 16_656 . ? F1 Mn1 N4 110.75(19) 16_656 . ? F1 Mn1 N4 88.75(19) . . ? F1 Mn1 N1 88.50(19) 16_656 . ? F1 Mn1 N1 110.10(19) . . ? N4 Mn1 N1 152.5(2) . . ? F1 Mn1 N2 158.26(18) 16_656 . ? F1 Mn1 N2 84.57(18) . . ? N4 Mn1 N2 90.9(2) . . ? N1 Mn1 N2 72.0(2) . . ? F1 Mn1 N3 91.90(18) 16_656 . ? F1 Mn1 N3 160.58(19) . . ? N4 Mn1 N3 71.9(2) . . ? N1 Mn1 N3 88.6(2) . . ? N2 Mn1 N3 96.99(19) . . ? Mn1 F1 Mn1 130.9(2) 14_566 . ? C7 N2 C6 118.4(6) . . ? C7 N2 Mn1 126.2(5) . . ? C6 N2 Mn1 115.4(5) . . ? C13 N3 C17 119.2(6) . . ? C13 N3 Mn1 127.2(5) . . ? C17 N3 Mn1 113.6(4) . . ? N2 C6 C10 121.4(7) . . ? N2 C6 C5 119.3(6) . . ? C10 C6 C5 119.3(7) . . ? C19 N4 C18 119.6(6) . . ? C19 N4 Mn1 123.6(5) . . ? C18 N4 Mn1 116.6(5) . . ? N3 C13 C14 122.6(7) . . ? N3 C13 H13 118.7 . . ? C14 C13 H13 118.7 . . ? C1 N1 C5 116.9(6) . . ? C1 N1 Mn1 126.0(5) . . ? C5 N1 Mn1 116.9(5) . . ? C9 C10 C6 117.8(7) . . ? C9 C10 C11 124.2(7) . . ? C6 C10 C11 118.0(7) . . ? N4 C18 C17 119.0(6) . . ? N4 C18 C22 120.4(7) . . ? C17 C18 C22 120.5(7) . . ? C17 C16 C24 119.7(7) . . ? C17 C16 C15 117.2(7) . . ? C24 C16 C15 123.0(7) . . ? C4 C5 N1 123.1(7) . . ? C4 C5 C6 120.7(7) . . ? N1 C5 C6 116.1(6) . . ? C9 C8 C7 118.3(7) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C14 C15 C16 119.9(7) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C3 C2 C1 116.8(8) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C11 C12 C4 120.8(7) . . ? C11 C12 H12 119.6 . . ? C4 C12 H12 119.6 . . ? C8 C9 C10 121.4(7) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C23 C24 C16 122.3(7) . . ? C23 C24 H24 118.9 . . ? C16 C24 H24 118.9 . . ? C15 C14 C13 119.2(7) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? N3 C17 C16 121.7(6) . . ? N3 C17 C18 118.8(6) . . ? C16 C17 C18 119.4(6) . . ? N1 C1 C2 124.7(8) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? N2 C7 C8 122.6(7) . . ? N2 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C12 C11 C10 121.3(7) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C5 C4 C3 118.4(7) . . ? C5 C4 C12 119.8(7) . . ? C3 C4 C12 121.7(7) . . ? C24 C23 C22 120.7(7) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C20 C21 C22 118.9(8) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C21 C22 C18 119.1(7) . . ? C21 C22 C23 123.5(7) . . ? C18 C22 C23 117.4(7) . . ? C2 C3 C4 120.0(7) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? N4 C19 C20 122.0(8) . . ? N4 C19 H19 119.0 . . ? C20 C19 H19 119.0 . . ? C21 C20 C19 119.8(8) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? O3 N5 O2 119.9(9) . . ? O3 N5 O1 119.9(9) . . ? O2 N5 O1 120.1(9) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.827 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.095