data_02080 _database_code_CSD 189527 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Tolman, William' 'Brooks, Neil R.' 'Hillmyer, Marc A.' 'Williams, Charlotte K.' _publ_contact_author_name 'Prof William Tolman' _publ_contact_author_address ; Chemistry University of Minnesota 207 Pleasant St. SE Minneapolis MN 55455 UNITED STATES OF AMERICA ; _publ_contact_author_email 'TOLMAN@CHEM.UMN.EDU' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Metalloenzyme inspired dizinc catalyst for the polymerisation of lactide ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 02080 _chemical_formula_moiety 'C21 H40 Cl2 N4 O2 Zn2, C4 H8 O' _chemical_formula_sum 'C25 H48 Cl2 N4 O3 Zn2' _chemical_formula_weight 654.31 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 17.3944(17) _cell_length_b 14.6134(14) _cell_length_c 11.9982(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3049.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2998 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 24.97 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 1.780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.715 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS 2.03 (Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 15361 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5355 _reflns_number_gt 4507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97' _computing_structure_refinement 'SHELXL-97' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^] 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 0.165(17) _refine_ls_number_reflns 5355 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Zn1 Zn 0.90086(4) 0.17832(4) 0.32113(7) 0.03094(18) Uani 1 1 d . . . Zn2 Zn 0.87040(3) 0.38856(4) 0.37156(6) 0.02938(17) Uani 1 1 d . . . Cl1 Cl 0.92555(8) 0.10346(9) 0.48781(10) 0.0284(3) Uani 1 1 d . . . Cl2 Cl 0.87356(7) 0.51418(8) 0.25076(11) 0.0229(3) Uani 1 1 d . . . O1 O 0.81250(19) 0.2707(2) 0.3650(4) 0.0342(9) Uani 1 1 d . . . O2 O 0.9491(2) 0.2997(3) 0.3027(4) 0.0378(10) Uani 1 1 d . . . O3 O 0.7743(5) -0.1663(5) 0.6605(8) 0.094(2) Uani 1 1 d . . . N1 N 0.8068(3) 0.0985(3) 0.2460(4) 0.0341(12) Uani 1 1 d . . . N2 N 0.9727(3) 0.0855(3) 0.2122(5) 0.0394(13) Uani 1 1 d . . . N3 N 0.7720(3) 0.4473(3) 0.4750(4) 0.0324(11) Uani 1 1 d . . . N4 N 0.9342(3) 0.4197(3) 0.5204(4) 0.0330(11) Uani 1 1 d . . . C1 C 0.5743(3) 0.2514(4) 0.3529(6) 0.0356(15) Uani 1 1 d . . . C2 C 0.6101(3) 0.3037(4) 0.4337(6) 0.0346(14) Uani 1 1 d . . . H2A H 0.5793 0.3353 0.4866 0.041 Uiso 1 1 calc R . . C3 C 0.6900(3) 0.3115(4) 0.4401(5) 0.0306(13) Uani 1 1 d . . . C4 C 0.7356(3) 0.2643(4) 0.3609(5) 0.0316(13) Uani 1 1 d . . . C5 C 0.7001(3) 0.2101(4) 0.2810(5) 0.0305(13) Uani 1 1 d . . . C6 C 0.6211(3) 0.2044(4) 0.2776(5) 0.0344(14) Uani 1 1 d . . . H6A H 0.5976 0.1672 0.2223 0.041 Uiso 1 1 calc R . . C7 C 0.4876(3) 0.2443(5) 0.3464(6) 0.0470(19) Uani 1 1 d . . . H7A H 0.4645 0.2816 0.4054 0.070 Uiso 1 1 calc R . . H7B H 0.4721 0.1803 0.3559 0.070 Uiso 1 1 calc R . . H7C H 0.4701 0.2664 0.2736 0.070 Uiso 1 1 calc R . . C8 C 0.7470(4) 0.1596(4) 0.1964(5) 0.0368(14) Uani 1 1 d . . . H8A H 0.7121 0.1221 0.1497 0.044 Uiso 1 1 calc R . . H8B H 0.7725 0.2046 0.1470 0.044 Uiso 1 1 calc R . . C9 C 0.7706(4) 0.0377(4) 0.3259(7) 0.0481(17) Uani 1 1 d . . . H9A H 0.7292 0.0036 0.2891 0.072 Uiso 1 1 calc R . . H9B H 0.7491 0.0737 0.3874 0.072 Uiso 1 1 calc R . . H9C H 0.8088 -0.0053 0.3551 0.072 Uiso 1 1 calc R . . C10 C 0.8427(4) 0.0432(5) 0.1535(6) 0.0487(17) Uani 1 1 d . . . H10A H 0.8088 -0.0091 0.1349 0.058 Uiso 1 1 calc R . . H10B H 0.8479 0.0818 0.0861 0.058 Uiso 1 1 calc R . . C11 C 0.9203(4) 0.0081(5) 0.1876(6) 0.0473(17) Uani 1 1 d . . . H11A H 0.9150 -0.0310 0.2545 0.057 Uiso 1 1 calc R . . H11B H 0.9421 -0.0296 0.1268 0.057 Uiso 1 1 calc R . . C12 C 0.9954(5) 0.1260(5) 0.1054(6) 0.0506(18) Uani 1 1 d . . . H12A H 1.0262 0.0818 0.0632 0.076 Uiso 1 1 calc R . . H12B H 1.0258 0.1813 0.1190 0.076 Uiso 1 1 calc R . . H12C H 0.9493 0.1419 0.0627 0.076 Uiso 1 1 calc R . . C13 C 1.0423(4) 0.0479(5) 0.2675(6) 0.0493(17) Uani 1 1 d . . . H13A H 1.0702 0.0087 0.2150 0.074 Uiso 1 1 calc R . . H13B H 1.0270 0.0119 0.3327 0.074 Uiso 1 1 calc R . . H13C H 1.0756 0.0984 0.2912 0.074 Uiso 1 1 calc R . . C14 C 0.7292(4) 0.3687(4) 0.5260(5) 0.0349(14) Uani 1 1 d . . . H14A H 0.7657 0.3301 0.5684 0.042 Uiso 1 1 calc R . . H14B H 0.6905 0.3926 0.5789 0.042 Uiso 1 1 calc R . . C15 C 0.7168(4) 0.5097(5) 0.4193(6) 0.0434(16) Uani 1 1 d . . . H15A H 0.6778 0.5295 0.4731 0.065 Uiso 1 1 calc R . . H15B H 0.6918 0.4775 0.3574 0.065 Uiso 1 1 calc R . . H15C H 0.7443 0.5633 0.3906 0.065 Uiso 1 1 calc R . . C16 C 0.8128(4) 0.5003(4) 0.5629(5) 0.0395(15) Uani 1 1 d . . . H16A H 0.7765 0.5143 0.6241 0.047 Uiso 1 1 calc R . . H16B H 0.8308 0.5590 0.5311 0.047 Uiso 1 1 calc R . . C17 C 0.8812(4) 0.4486(5) 0.6098(6) 0.0413(16) Uani 1 1 d . . . H17A H 0.9090 0.4883 0.6632 0.050 Uiso 1 1 calc R . . H17B H 0.8628 0.3941 0.6508 0.050 Uiso 1 1 calc R . . C18 C 0.9879(4) 0.4946(5) 0.4909(6) 0.0431(15) Uani 1 1 d . . . H18A H 1.0185 0.5112 0.5565 0.065 Uiso 1 1 calc R . . H18B H 0.9586 0.5479 0.4656 0.065 Uiso 1 1 calc R . . H18C H 1.0223 0.4741 0.4311 0.065 Uiso 1 1 calc R . . C19 C 0.9803(4) 0.3426(5) 0.5594(6) 0.0495(18) Uani 1 1 d . . . H19A H 1.0081 0.3603 0.6271 0.074 Uiso 1 1 calc R . . H19B H 1.0173 0.3252 0.5014 0.074 Uiso 1 1 calc R . . H19C H 0.9466 0.2906 0.5758 0.074 Uiso 1 1 calc R . . C20 C 1.0074(4) 0.3354(5) 0.2354(7) 0.0491(18) Uani 1 1 d . . . H20A H 1.0011 0.4025 0.2301 0.059 Uiso 1 1 calc R . . H20B H 1.0024 0.3097 0.1594 0.059 Uiso 1 1 calc R . . C21 C 1.0867(4) 0.3141(5) 0.2797(8) 0.058(2) Uani 1 1 d . . . H21A H 1.1255 0.3402 0.2296 0.087 Uiso 1 1 calc R . . H21B H 1.0936 0.2477 0.2840 0.087 Uiso 1 1 calc R . . H21C H 1.0926 0.3408 0.3542 0.087 Uiso 1 1 calc R . . C22 C 0.7912(6) -0.1750(9) 0.5469(11) 0.100(4) Uani 1 1 d . . . H22A H 0.8264 -0.2272 0.5341 0.120 Uiso 1 1 calc R . . H22B H 0.8158 -0.1186 0.5185 0.120 Uiso 1 1 calc R . . C23 C 0.7162(8) -0.1908(13) 0.4902(11) 0.148(7) Uani 1 1 d . . . H23A H 0.6935 -0.1324 0.4645 0.178 Uiso 1 1 calc R . . H23B H 0.7224 -0.2321 0.4254 0.178 Uiso 1 1 calc R . . C24 C 0.6687(7) -0.2327(8) 0.5749(11) 0.100(4) Uani 1 1 d . . . H24A H 0.6577 -0.2972 0.5554 0.120 Uiso 1 1 calc R . . H24B H 0.6194 -0.1995 0.5820 0.120 Uiso 1 1 calc R . . C25 C 0.7118(6) -0.2279(8) 0.6785(12) 0.096(4) Uani 1 1 d . . . H25A H 0.6785 -0.2052 0.7395 0.115 Uiso 1 1 calc R . . H25B H 0.7313 -0.2892 0.6992 0.115 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0329(3) 0.0292(3) 0.0307(3) 0.0006(3) 0.0014(3) 0.0033(3) Zn2 0.0322(3) 0.0281(3) 0.0278(3) 0.0004(3) -0.0017(3) -0.0039(3) Cl1 0.0434(8) 0.0277(7) 0.0142(6) 0.0059(5) -0.0014(6) 0.0112(6) Cl2 0.0258(6) 0.0250(6) 0.0180(6) 0.0082(5) -0.0003(5) -0.0048(5) O1 0.0223(19) 0.0258(19) 0.054(3) -0.006(2) -0.0004(19) -0.0027(15) O2 0.034(2) 0.037(2) 0.042(3) 0.000(2) 0.009(2) -0.0067(17) O3 0.086(5) 0.094(5) 0.103(6) -0.003(4) -0.017(4) -0.016(4) N1 0.040(3) 0.029(3) 0.033(3) 0.001(2) 0.003(2) 0.001(2) N2 0.045(3) 0.031(3) 0.043(3) -0.006(2) 0.008(2) 0.007(2) N3 0.035(3) 0.033(3) 0.029(3) -0.005(2) 0.004(2) 0.001(2) N4 0.035(3) 0.033(3) 0.031(3) -0.001(2) -0.010(2) -0.001(2) C1 0.029(3) 0.031(3) 0.048(4) 0.010(3) -0.004(3) -0.003(2) C2 0.033(3) 0.028(3) 0.043(4) -0.002(3) 0.008(3) 0.002(2) C3 0.034(3) 0.024(3) 0.033(3) 0.002(2) 0.003(3) 0.000(2) C4 0.030(3) 0.027(3) 0.037(3) 0.006(3) 0.003(3) -0.001(2) C5 0.036(3) 0.028(3) 0.028(3) 0.005(2) 0.002(2) -0.005(2) C6 0.038(3) 0.027(3) 0.038(4) 0.000(3) -0.005(3) -0.002(3) C7 0.026(3) 0.055(4) 0.061(6) 0.009(3) -0.003(3) -0.003(3) C8 0.040(3) 0.035(3) 0.036(4) -0.002(3) -0.003(3) 0.010(3) C9 0.049(4) 0.034(3) 0.062(5) 0.010(3) 0.014(4) 0.001(3) C10 0.053(4) 0.038(4) 0.055(5) -0.026(3) 0.000(3) -0.001(3) C11 0.052(4) 0.033(4) 0.057(5) -0.009(3) 0.003(3) 0.012(3) C12 0.069(5) 0.046(4) 0.037(4) 0.005(3) 0.007(4) 0.010(4) C13 0.050(4) 0.046(4) 0.052(4) -0.004(3) -0.001(3) 0.010(3) C14 0.036(3) 0.037(3) 0.032(3) 0.000(3) 0.004(3) -0.004(3) C15 0.043(4) 0.041(4) 0.046(4) 0.002(3) 0.003(3) 0.000(3) C16 0.040(4) 0.041(4) 0.038(4) -0.008(3) 0.004(3) -0.009(3) C17 0.048(4) 0.041(4) 0.035(4) -0.004(3) 0.005(3) -0.015(3) C18 0.046(4) 0.044(4) 0.039(4) 0.002(3) -0.009(3) -0.015(3) C19 0.057(4) 0.054(4) 0.038(4) 0.003(3) -0.017(3) 0.003(3) C20 0.050(4) 0.043(4) 0.055(5) 0.001(3) 0.013(3) 0.001(3) C21 0.050(4) 0.050(4) 0.073(6) -0.003(4) -0.003(4) 0.009(3) C22 0.075(7) 0.138(11) 0.087(9) 0.006(8) 0.007(6) -0.015(7) C23 0.099(9) 0.28(2) 0.066(8) 0.000(10) -0.012(7) -0.063(11) C24 0.087(8) 0.094(8) 0.121(10) -0.030(7) 0.004(8) -0.033(6) C25 0.070(6) 0.081(7) 0.137(11) -0.015(7) -0.007(7) -0.021(6) _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 Zn1 O2 1.975(4) . ? Zn1 O1 2.112(4) . ? Zn1 N1 2.202(5) . ? Zn1 N2 2.261(5) . ? Zn1 Cl1 2.3197(15) . ? Zn2 O1 1.997(3) . ? Zn2 O2 2.060(4) . ? Zn2 N4 2.151(5) . ? Zn2 N3 2.282(5) . ? Zn2 Cl2 2.3396(13) . ? O1 C4 1.342(6) . ? O2 C20 1.396(8) . ? O3 C22 1.399(15) . ? O3 C25 1.428(13) . ? N1 C9 1.452(8) . ? N1 C8 1.494(8) . ? N1 C10 1.508(8) . ? N2 C12 1.465(9) . ? N2 C11 1.482(9) . ? N2 C13 1.486(9) . ? N3 C15 1.482(8) . ? N3 C16 1.489(8) . ? N3 C14 1.499(8) . ? N4 C19 1.460(8) . ? N4 C17 1.477(8) . ? N4 C18 1.483(8) . ? C1 C2 1.382(9) . ? C1 C6 1.397(9) . ? C1 C7 1.513(8) . ? C2 C3 1.398(8) . ? C3 C4 1.415(9) . ? C3 C14 1.492(9) . ? C4 C5 1.389(8) . ? C5 C6 1.378(8) . ? C5 C8 1.497(9) . ? C10 C11 1.501(10) . ? C16 C17 1.516(9) . ? C20 C21 1.511(10) . ? C22 C23 1.489(16) . ? C23 C24 1.444(18) . ? C24 C25 1.453(18) . ? 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 Zn1 O1 76.31(15) . . ? O2 Zn1 N1 138.22(18) . . ? O1 Zn1 N1 84.27(16) . . ? O2 Zn1 N2 103.84(18) . . ? O1 Zn1 N2 158.42(19) . . ? N1 Zn1 N2 81.72(19) . . ? O2 Zn1 Cl1 116.19(14) . . ? O1 Zn1 Cl1 102.77(14) . . ? N1 Zn1 Cl1 103.93(14) . . ? N2 Zn1 Cl1 96.50(15) . . ? O1 Zn2 O2 77.06(15) . . ? O1 Zn2 N4 118.36(19) . . ? O2 Zn2 N4 97.06(18) . . ? O1 Zn2 N3 88.13(17) . . ? O2 Zn2 N3 162.55(17) . . ? N4 Zn2 N3 81.75(18) . . ? O1 Zn2 Cl2 131.64(14) . . ? O2 Zn2 Cl2 103.32(13) . . ? N4 Zn2 Cl2 109.66(14) . . ? N3 Zn2 Cl2 93.39(13) . . ? C4 O1 Zn2 124.3(3) . . ? C4 O1 Zn1 132.2(3) . . ? Zn2 O1 Zn1 101.19(15) . . ? C20 O2 Zn1 135.1(4) . . ? C20 O2 Zn2 118.6(4) . . ? Zn1 O2 Zn2 103.79(17) . . ? C22 O3 C25 104.5(9) . . ? C9 N1 C8 109.0(5) . . ? C9 N1 C10 109.7(5) . . ? C8 N1 C10 108.4(5) . . ? C9 N1 Zn1 112.1(4) . . ? C8 N1 Zn1 111.4(4) . . ? C10 N1 Zn1 106.2(4) . . ? C12 N2 C11 107.4(5) . . ? C12 N2 C13 108.7(6) . . ? C11 N2 C13 108.0(5) . . ? C12 N2 Zn1 114.3(4) . . ? C11 N2 Zn1 103.5(4) . . ? C13 N2 Zn1 114.5(4) . . ? C15 N3 C16 108.0(5) . . ? C15 N3 C14 109.5(5) . . ? C16 N3 C14 110.2(5) . . ? C15 N3 Zn2 118.2(4) . . ? C16 N3 Zn2 102.8(4) . . ? C14 N3 Zn2 107.8(4) . . ? C19 N4 C17 109.4(5) . . ? C19 N4 C18 107.4(5) . . ? C17 N4 C18 110.8(5) . . ? C19 N4 Zn2 112.7(4) . . ? C17 N4 Zn2 110.0(4) . . ? C18 N4 Zn2 106.4(4) . . ? C2 C1 C6 117.6(5) . . ? C2 C1 C7 121.5(6) . . ? C6 C1 C7 120.9(6) . . ? C1 C2 C3 122.1(6) . . ? C2 C3 C4 118.7(5) . . ? C2 C3 C14 122.6(5) . . ? C4 C3 C14 118.7(5) . . ? O1 C4 C5 120.5(5) . . ? O1 C4 C3 120.0(5) . . ? C5 C4 C3 119.5(5) . . ? C6 C5 C4 119.9(6) . . ? C6 C5 C8 119.6(5) . . ? C4 C5 C8 120.5(5) . . ? C5 C6 C1 122.2(6) . . ? N1 C8 C5 113.8(5) . . ? C11 C10 N1 110.8(6) . . ? N2 C11 C10 110.3(5) . . ? C3 C14 N3 111.9(5) . . ? N3 C16 C17 112.3(5) . . ? N4 C17 C16 111.2(5) . . ? O2 C20 C21 112.5(6) . . ? O3 C22 C23 106.0(10) . . ? C24 C23 C22 104.2(11) . . ? C23 C24 C25 106.7(10) . . ? O3 C25 C24 107.1(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.986 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.099