# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_date 01-02-05 _publ_contact_author_name 'Pierre Braunstein' _publ_contact_author_address ; Institut Le Bel, rue Blaise Pascal, 67000 STRASBOURG, FRANCE ; _publ_contact_author_phone 0390241308 _publ_contact_author_fax 0390241322 _publ_contact_author_email braunst@chimie.u-strasbg.fr _publ_section_title ; First Transamination Reactions for the One-Pot Synthesis of Substituted Zwitterionic Quinones ; loop_ _publ_author_name _publ_author_address 'Qing-Zheng Yang.' ; Laboratoire de Chimie de Coordination, UMR CNRS 7513 Universite Louis Pasteur 4 rue Blaise Pascal Strasbourg France ; 'Olivier Siri' ; Laboratoire de Chimie de Coordination, UMR CNRS 7513 Universite Louis Pasteur 4 rue Blaise Pascal Strasbourg France ; 'Pierre Braunstein' ; Laboratoire de Chimie de Coordination, UMR CNRS 7513 Universite Louis Pasteur 4 rue Blaise Pascal Strasbourg France ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. A.L. Spek, PLATON 98, Utrecht University, The Netherland, 1998. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. University of Gottingen. Germany. ; data_shelxs97 _database_code_depnum_ccdc_archive 'CCDC 262674' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 N2 O4' _chemical_formula_sum 'C10 H14 N2 O4' _chemical_formula_weight 226.23 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' O O 0.0106 0.0060 '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' _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 5.2310(10) _cell_length_b 9.8570(10) _cell_length_c 10.5170(10) _cell_angle_alpha 74.67(5) _cell_angle_beta 76.63(5) _cell_angle_gamma 85.42(5) _cell_volume 508.71(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5844 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.115 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_reflns_av_R_equivalents 0.073 _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2961 _diffrn_reflns_av_sigmaI/netI 0.1573 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 30.18 _reflns_number_total 2960 _reflns_number_gt 2106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (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^)+(0.0002P)^2^+0.8805P] 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 SHELXL _refine_ls_extinction_coef 0.038(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2960 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1802 _refine_ls_R_factor_gt 0.1206 _refine_ls_wR_factor_ref 0.2485 _refine_ls_wR_factor_gt 0.2239 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.3155(6) 0.9418(3) 0.4304(3) 0.0245(7) Uani 1 1 d . . . O1 O -0.2630(6) 0.6016(3) 0.4270(3) 0.0254(8) Uani 1 1 d . . . N1 N -0.3706(7) 0.5219(3) 0.6912(3) 0.0163(7) Uani 1 1 d . . . N2 N 0.2168(7) 0.8679(4) 0.6947(3) 0.0169(7) Uani 1 1 d . . . O4 O 0.5809(6) 0.9566(3) 0.8418(3) 0.0247(8) Uani 1 1 d . . . C1 C 0.0298(8) 0.7772(4) 0.4148(4) 0.0176(8) Uani 1 1 d . . . O3 O -0.8503(6) 0.3442(4) 0.8475(3) 0.0282(8) Uani 1 1 d . . . C4 C -0.0822(8) 0.6904(4) 0.7085(4) 0.0159(8) Uani 1 1 d . . . C5 C 0.0931(7) 0.7977(4) 0.6374(4) 0.0138(8) Uani 1 1 d . . . C6 C 0.1557(7) 0.8436(4) 0.4841(4) 0.0162(8) Uani 1 1 d . . . C2 C -0.1470(8) 0.6688(4) 0.4827(4) 0.0165(8) Uani 1 1 d . . . C3 C -0.2018(7) 0.6241(4) 0.6359(4) 0.0137(8) Uani 1 1 d . . . C10 C 0.3031(8) 0.9610(4) 0.8767(4) 0.0175(9) Uani 1 1 d . . . C8 C -0.5916(8) 0.3229(4) 0.8691(5) 0.0198(9) Uani 1 1 d . . . C7 C -0.4466(9) 0.4595(4) 0.8366(4) 0.0172(9) Uani 1 1 d . . . C9 C 0.1808(8) 0.8465(4) 0.8406(4) 0.0163(8) Uani 1 1 d . . . H1 H 0.054(8) 0.811(4) 0.315(4) 0.013(3) Uiso 1 1 d . . . H2 H -0.118(8) 0.661(4) 0.801(5) 0.013(3) Uiso 1 1 d . . . H3 H -0.424(8) 0.492(4) 0.636(4) 0.013(3) Uiso 1 1 d . . . H4 H -0.570(8) 0.520(4) 0.877(4) 0.013(3) Uiso 1 1 d . . . H5 H -0.295(9) 0.440(4) 0.867(4) 0.013(3) Uiso 1 1 d . . . H6 H -0.611(8) 0.281(4) 0.965(5) 0.013(3) Uiso 1 1 d . . . H7 H -0.497(8) 0.263(5) 0.820(4) 0.013(3) Uiso 1 1 d . . . H8 H -0.836(8) 0.360(5) 0.768(5) 0.013(3) Uiso 1 1 d . . . H9 H 0.309(9) 0.931(5) 0.642(4) 0.013(3) Uiso 1 1 d . . . H10 H -0.002(9) 0.855(4) 0.875(4) 0.013(3) Uiso 1 1 d . . . H11 H 0.256(8) 0.769(5) 0.877(4) 0.013(3) Uiso 1 1 d . . . H12 H 0.253(8) 0.941(4) 0.979(4) 0.013(3) Uiso 1 1 d . . . H13 H 0.243(8) 1.048(5) 0.838(4) 0.013(3) Uiso 1 1 d . . . H14 H 0.630(9) 0.981(5) 0.768(5) 0.013(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 O2 0.0281(17) 0.0288(16) 0.0163(15) -0.0017(12) -0.0028(12) -0.0179(13) O1 0.0306(17) 0.0330(17) 0.0155(15) -0.0064(12) -0.0037(13) -0.0204(14) N1 0.0234(18) 0.0177(16) 0.0103(16) -0.0043(13) -0.0044(13) -0.0107(14) N2 0.0222(18) 0.0161(16) 0.0126(17) -0.0011(13) -0.0042(14) -0.0086(14) O4 0.0192(16) 0.0389(19) 0.0152(15) -0.0021(14) -0.0045(13) -0.0102(13) C1 0.021(2) 0.020(2) 0.0098(18) -0.0016(15) -0.0008(16) -0.0074(16) O3 0.0213(16) 0.047(2) 0.0149(15) -0.0032(14) -0.0010(13) -0.0160(14) C4 0.020(2) 0.0181(19) 0.0108(18) -0.0039(15) -0.0033(15) -0.0049(16) C5 0.0139(18) 0.0159(18) 0.0114(17) -0.0022(14) -0.0034(15) -0.0029(15) C6 0.0133(19) 0.021(2) 0.0164(19) -0.0050(16) -0.0066(15) -0.0010(16) C2 0.022(2) 0.0166(19) 0.0118(18) -0.0051(14) -0.0023(15) -0.0035(16) C3 0.0150(19) 0.0147(18) 0.0097(17) 0.0002(14) -0.0010(15) -0.0063(14) C10 0.022(2) 0.017(2) 0.016(2) -0.0063(16) -0.0096(16) 0.0001(16) C8 0.018(2) 0.0156(19) 0.021(2) 0.0020(16) 0.0002(17) -0.0064(16) C7 0.022(2) 0.017(2) 0.0113(18) -0.0004(15) -0.0011(16) -0.0083(17) C9 0.019(2) 0.0174(19) 0.0135(19) -0.0018(15) -0.0065(16) -0.0054(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 O2 C6 1.256(5) . ? O1 C2 1.258(5) . ? N1 C3 1.315(5) . ? N1 C7 1.461(5) . ? N1 H3 0.83(5) . ? N2 C5 1.317(5) . ? N2 C9 1.462(5) . ? N2 H9 0.82(5) . ? O4 C10 1.414(5) . ? O4 H14 0.74(5) . ? C1 C6 1.392(5) . ? C1 C2 1.398(5) . ? C1 H1 1.00(4) . ? O3 C8 1.414(5) . ? O3 H8 0.80(5) . ? C4 C5 1.392(5) . ? C4 C3 1.396(5) . ? C4 H2 0.92(4) . ? C5 C6 1.517(5) . ? C2 C3 1.519(5) . ? C10 C9 1.511(5) . ? C10 H12 1.01(4) . ? C10 H13 0.91(4) . ? C8 C7 1.518(5) . ? C8 H6 0.96(4) . ? C8 H7 0.92(4) . ? C7 H4 0.95(4) . ? C7 H5 0.91(4) . ? C9 H10 0.95(4) . ? C9 H11 0.87(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C7 123.7(3) . . ? C3 N1 H3 114(3) . . ? C7 N1 H3 122(3) . . ? C5 N2 C9 124.4(3) . . ? C5 N2 H9 115(3) . . ? C9 N2 H9 121(3) . . ? C10 O4 H14 111(4) . . ? C6 C1 C2 121.7(4) . . ? C6 C1 H1 120(2) . . ? C2 C1 H1 118(2) . . ? C8 O3 H8 106(3) . . ? C5 C4 C3 118.6(4) . . ? C5 C4 H2 122(3) . . ? C3 C4 H2 119(3) . . ? N2 C5 C4 124.1(4) . . ? N2 C5 C6 114.3(3) . . ? C4 C5 C6 121.6(3) . . ? O2 C6 C1 125.3(4) . . ? O2 C6 C5 116.3(3) . . ? C1 C6 C5 118.4(3) . . ? O1 C2 C1 125.3(4) . . ? O1 C2 C3 116.2(3) . . ? C1 C2 C3 118.5(3) . . ? N1 C3 C4 124.5(3) . . ? N1 C3 C2 114.3(3) . . ? C4 C3 C2 121.2(3) . . ? O4 C10 C9 112.8(3) . . ? O4 C10 H12 106(2) . . ? C9 C10 H12 106(2) . . ? O4 C10 H13 110(3) . . ? C9 C10 H13 111(3) . . ? H12 C10 H13 111(4) . . ? O3 C8 C7 112.8(4) . . ? O3 C8 H6 105(3) . . ? C7 C8 H6 107(2) . . ? O3 C8 H7 111(3) . . ? C7 C8 H7 110(3) . . ? H6 C8 H7 110(4) . . ? N1 C7 C8 112.0(3) . . ? N1 C7 H4 110(3) . . ? C8 C7 H4 104(3) . . ? N1 C7 H5 107(3) . . ? C8 C7 H5 108(3) . . ? H4 C7 H5 116(4) . . ? N2 C9 C10 112.5(3) . . ? N2 C9 H10 107(3) . . ? C10 C9 H10 105(3) . . ? N2 C9 H11 111(3) . . ? C10 C9 H11 105(3) . . ? H10 C9 H11 116(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N2 C5 C4 -2.2(7) . . . . ? C9 N2 C5 C6 177.5(4) . . . . ? C3 C4 C5 N2 179.8(4) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C2 C1 C6 O2 -179.7(4) . . . . ? C2 C1 C6 C5 -1.2(6) . . . . ? N2 C5 C6 O2 -0.1(5) . . . . ? C4 C5 C6 O2 179.7(4) . . . . ? N2 C5 C6 C1 -178.7(4) . . . . ? C4 C5 C6 C1 1.1(6) . . . . ? C6 C1 C2 O1 -178.1(4) . . . . ? C6 C1 C2 C3 0.3(6) . . . . ? C7 N1 C3 C4 -2.9(7) . . . . ? C7 N1 C3 C2 178.2(4) . . . . ? C5 C4 C3 N1 -179.9(4) . . . . ? C5 C4 C3 C2 -1.0(6) . . . . ? O1 C2 C3 N1 -1.6(5) . . . . ? C1 C2 C3 N1 179.9(4) . . . . ? O1 C2 C3 C4 179.4(4) . . . . ? C1 C2 C3 C4 0.9(6) . . . . ? C3 N1 C7 C8 -166.5(4) . . . . ? O3 C8 C7 N1 -73.0(5) . . . . ? C5 N2 C9 C10 -168.0(4) . . . . ? O4 C10 C9 N2 -69.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.18 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.419 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.081 data_welt37 _database_code_depnum_ccdc_archive 'CCDC 262675' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 N8 O4 Zn' _chemical_formula_sum 'C28 H46 N8 O4 Zn' _chemical_formula_weight 624.10 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.309(5) _cell_length_b 17.060(5) _cell_length_c 15.059(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.02(5) _cell_angle_gamma 90.00 _cell_volume 3144.8(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8005 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16077 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 29.99 _reflns_number_total 9138 _reflns_number_gt 5303 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (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. Atoms C12, C13, C14, N7, C27 and C28 were refined isotropically owing to large thermal agitation in the chain ends. ; _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^)+(0.0600P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9138 _refine_ls_number_parameters 335 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1396 _refine_ls_R_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.2402 _refine_ls_wR_factor_gt 0.2129 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.004 _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 Zn Zn 0.31007(5) 0.14097(4) 0.44817(4) 0.04108(19) Uani 1 1 d . . . O3 O 0.2876(3) 0.0276(2) 0.5014(2) 0.0437(9) Uani 1 1 d . . . C16 C 0.2024(4) 0.0223(3) 0.5423(3) 0.0376(11) Uani 1 1 d . . . O1 O 0.2560(3) 0.1049(2) 0.3151(2) 0.0465(9) Uani 1 1 d . . . C19 C 0.0033(4) 0.0250(4) 0.6258(3) 0.0413(12) Uani 1 1 d . . . C2 C 0.3337(4) 0.0926(3) 0.2677(3) 0.0386(11) Uani 1 1 d . . . O4 O 0.0233(3) -0.1124(3) 0.6402(3) 0.0588(11) Uani 1 1 d . . . C18 C 0.0421(4) 0.0947(4) 0.5976(4) 0.0435(12) Uani 1 1 d . . . H18 H 0.0040 0.1418 0.6072 0.052 Uiso 1 1 calc . . . N1 N 0.4536(3) 0.1229(3) 0.3952(3) 0.0402(10) Uani 1 1 d . . . C3 C 0.4495(4) 0.1005(3) 0.3129(3) 0.0350(10) Uani 1 1 d . . . N3 N 0.1808(3) 0.1579(3) 0.5183(3) 0.0405(10) Uani 1 1 d . . . C17 C 0.1389(4) 0.0971(3) 0.5539(3) 0.0381(11) Uani 1 1 d . . . C25 C -0.1706(5) 0.0744(4) 0.6716(4) 0.0562(16) Uani 1 1 d . . . H25A H -0.2439 0.0502 0.6687 0.067 Uiso 1 1 calc . . . H25B H -0.1710 0.1124 0.6218 0.067 Uiso 1 1 calc . . . C21 C 0.1272(5) 0.2339(4) 0.5170(4) 0.0525(15) Uani 1 1 d . . . H21A H 0.1100 0.2478 0.5778 0.063 Uiso 1 1 calc . . . H21B H 0.0580 0.2321 0.4770 0.063 Uiso 1 1 calc . . . N5 N 0.4487(4) 0.1685(3) 0.5724(3) 0.0490(12) Uani 1 1 d . . . C6 C 0.4070(5) 0.0560(3) 0.1286(4) 0.0507(14) Uani 1 1 d . . . C15 C 0.1644(4) -0.0467(4) 0.5762(4) 0.0443(12) Uani 1 1 d . . . H15 H 0.2069 -0.0930 0.5734 0.053 Uiso 1 1 calc . . . N4 N -0.0901(4) 0.0143(3) 0.6610(3) 0.0497(12) Uani 1 1 d . . . HN4 H -0.1042 -0.0332 0.6793 0.060 Uiso 1 1 calc . . . N6 N 0.2521(4) 0.2664(3) 0.4042(3) 0.0498(12) Uani 1 1 d . . . C20 C 0.0649(4) -0.0511(4) 0.6147(4) 0.0441(12) Uani 1 1 d . . . O2 O 0.3971(4) 0.0374(3) 0.0486(3) 0.0711(14) Uani 1 1 d . . . C22 C 0.2033(5) 0.2945(4) 0.4837(4) 0.0568(16) Uani 1 1 d . . . H22A H 0.1622 0.3434 0.4687 0.068 Uiso 1 1 calc . . . H22B H 0.2622 0.3065 0.5317 0.068 Uiso 1 1 calc . . . C7 C 0.5566(4) 0.1287(4) 0.4516(4) 0.0523(15) Uani 1 1 d . . . H7A H 0.5893 0.1812 0.4459 0.063 Uiso 1 1 calc . . . H7B H 0.6087 0.0888 0.4342 0.063 Uiso 1 1 calc . . . C5 C 0.5217(5) 0.0601(3) 0.1772(4) 0.0480(14) Uani 1 1 d . . . C4 C 0.5390(4) 0.0820(3) 0.2649(3) 0.0422(12) Uani 1 1 d . . . H4 H 0.6113 0.0849 0.2936 0.051 Uiso 1 1 calc . . . N2 N 0.5992(5) 0.0417(4) 0.1262(4) 0.0632(15) Uani 1 1 d . . . H2 H 0.5797 0.0306 0.0697 0.076 Uiso 1 1 calc . . . C8 C 0.5301(6) 0.1145(5) 0.5505(5) 0.077(2) Uani 1 1 d . . . H8A H 0.5037 0.0602 0.5569 0.092 Uiso 1 1 calc . . . H8B H 0.5972 0.1215 0.5921 0.092 Uiso 1 1 calc . . . C1 C 0.3192(5) 0.0726(4) 0.1782(4) 0.0466(13) Uani 1 1 d . . . H1 H 0.2469 0.0699 0.1491 0.056 Uiso 1 1 calc . . . C24 C 0.3412(6) 0.3181(5) 0.3823(5) 0.0695(19) Uani 1 1 d . . . H24A H 0.3727 0.2976 0.3299 0.104 Uiso 1 1 calc . . . H24B H 0.3978 0.3203 0.4332 0.104 Uiso 1 1 calc . . . H24C H 0.3124 0.3709 0.3694 0.104 Uiso 1 1 calc . . . C23 C 0.1686(6) 0.2634(4) 0.3265(5) 0.0676(18) Uani 1 1 d . . . H23A H 0.1095 0.2281 0.3396 0.101 Uiso 1 1 calc . . . H23B H 0.2018 0.2440 0.2744 0.101 Uiso 1 1 calc . . . H23C H 0.1391 0.3160 0.3140 0.101 Uiso 1 1 calc . . . C26 C -0.1472(8) 0.1171(5) 0.7590(5) 0.081(2) Uani 1 1 d . . . H26A H -0.1440 0.0792 0.8089 0.097 Uiso 1 1 calc . . . H26B H -0.0755 0.1437 0.7610 0.097 Uiso 1 1 calc . . . C11 C 0.7137(7) 0.0387(5) 0.1581(6) 0.083(3) Uani 1 1 d . . . H11A H 0.7236 0.0114 0.2164 0.099 Uiso 1 1 calc . . . H11B H 0.7537 0.0089 0.1154 0.099 Uiso 1 1 calc . . . C10 C 0.4044(7) 0.1447(10) 0.6550(5) 0.142(6) Uani 1 1 d . . . H10A H 0.3467 0.1813 0.6680 0.212 Uiso 1 1 calc . . . H10B H 0.4629 0.1452 0.7045 0.212 Uiso 1 1 calc . . . H10C H 0.3740 0.0917 0.6479 0.212 Uiso 1 1 calc . . . N8 N -0.2335(8) 0.1755(4) 0.7691(5) 0.102(3) Uani 1 1 d D . . C9 C 0.4904(11) 0.2461(7) 0.5897(10) 0.165(7) Uani 1 1 d . . . H9A H 0.4305 0.2810 0.6023 0.248 Uiso 1 1 calc . . . H9B H 0.5231 0.2654 0.5373 0.248 Uiso 1 1 calc . . . H9C H 0.5459 0.2451 0.6413 0.248 Uiso 1 1 calc . . . C12 C 0.7533(13) 0.1100(9) 0.1668(11) 0.181(3) Uiso 1 1 d D . . H12A H 0.8147 0.1120 0.2148 0.217 Uiso 1 1 calc . . . H12B H 0.6961 0.1472 0.1817 0.217 Uiso 1 1 calc . . . N7 N 0.7954(11) 0.1323(7) 0.0706(9) 0.181(3) Uiso 1 1 d D . . C13 C 0.8261(14) 0.2214(8) 0.0872(11) 0.181(3) Uiso 1 1 d D . . H13A H 0.8731 0.2266 0.1435 0.271 Uiso 1 1 calc . . . H13B H 0.7593 0.2521 0.0903 0.271 Uiso 1 1 calc . . . H13C H 0.8649 0.2408 0.0380 0.271 Uiso 1 1 calc . . . C14 C 0.8937(12) 0.0745(10) 0.0747(11) 0.181(3) Uiso 1 1 d D . . H14A H 0.8665 0.0209 0.0647 0.271 Uiso 1 1 calc . . . H14B H 0.9359 0.0779 0.1334 0.271 Uiso 1 1 calc . . . H14C H 0.9406 0.0883 0.0283 0.271 Uiso 1 1 calc . . . C27 C -0.1821(13) 0.2410(9) 0.8305(10) 0.181(3) Uiso 1 1 d D . . H27A H -0.1534 0.2184 0.8881 0.271 Uiso 1 1 calc . . . H27B H -0.2377 0.2803 0.8400 0.271 Uiso 1 1 calc . . . H27C H -0.1224 0.2658 0.8026 0.271 Uiso 1 1 calc . . . C28 C -0.3236(12) 0.1420(10) 0.8188(11) 0.181(3) Uiso 1 1 d D . . H28A H -0.3652 0.1032 0.7811 0.271 Uiso 1 1 calc . . . H28B H -0.3725 0.1842 0.8336 0.271 Uiso 1 1 calc . . . H28C H -0.2915 0.1167 0.8739 0.271 Uiso 1 1 calc . . . 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 Zn 0.0349(3) 0.0530(4) 0.0379(3) -0.0028(3) 0.0160(2) 0.0029(3) O3 0.0336(18) 0.051(2) 0.049(2) -0.0018(17) 0.0177(16) 0.0040(16) C16 0.030(2) 0.050(3) 0.033(2) 0.000(2) 0.0075(19) 0.005(2) O1 0.0375(19) 0.062(2) 0.041(2) -0.0063(18) 0.0121(16) -0.0049(18) C19 0.027(2) 0.065(4) 0.032(2) -0.001(2) 0.0038(19) -0.004(2) C2 0.045(3) 0.037(3) 0.036(3) -0.002(2) 0.013(2) -0.004(2) O4 0.050(2) 0.063(3) 0.066(3) 0.015(2) 0.016(2) -0.006(2) C18 0.034(3) 0.057(3) 0.042(3) -0.004(2) 0.015(2) 0.006(2) N1 0.035(2) 0.050(3) 0.037(2) -0.0054(19) 0.0109(17) 0.0014(19) C3 0.039(3) 0.033(3) 0.036(2) -0.002(2) 0.017(2) -0.002(2) N3 0.033(2) 0.048(3) 0.043(2) -0.001(2) 0.0140(18) 0.0042(19) C17 0.030(2) 0.054(3) 0.033(2) -0.002(2) 0.0094(19) 0.004(2) C25 0.037(3) 0.071(4) 0.064(4) -0.007(3) 0.021(3) -0.003(3) C21 0.049(3) 0.052(3) 0.061(4) 0.003(3) 0.025(3) 0.011(3) N5 0.043(3) 0.064(3) 0.042(2) -0.015(2) 0.010(2) 0.006(2) C6 0.071(4) 0.045(3) 0.039(3) -0.007(2) 0.021(3) -0.004(3) C15 0.035(3) 0.053(3) 0.046(3) 0.005(3) 0.009(2) 0.007(2) N4 0.034(2) 0.068(3) 0.050(3) 0.002(2) 0.017(2) -0.001(2) N6 0.049(3) 0.054(3) 0.048(3) 0.004(2) 0.015(2) -0.001(2) C20 0.034(3) 0.060(4) 0.038(3) 0.005(3) 0.005(2) -0.002(2) O2 0.090(4) 0.086(4) 0.040(2) -0.021(2) 0.019(2) 0.002(3) C22 0.060(4) 0.048(3) 0.066(4) 0.000(3) 0.021(3) 0.007(3) C7 0.033(3) 0.080(4) 0.045(3) -0.014(3) 0.009(2) 0.008(3) C5 0.064(4) 0.040(3) 0.045(3) -0.005(2) 0.029(3) -0.001(3) C4 0.043(3) 0.045(3) 0.042(3) -0.005(2) 0.022(2) 0.000(2) N2 0.068(4) 0.073(4) 0.054(3) -0.016(3) 0.033(3) -0.006(3) C8 0.053(4) 0.100(6) 0.075(5) -0.020(4) -0.004(3) 0.012(4) C1 0.049(3) 0.052(3) 0.039(3) -0.007(2) 0.008(2) -0.005(3) C24 0.070(4) 0.069(5) 0.074(5) 0.009(4) 0.027(4) -0.011(4) C23 0.069(4) 0.068(5) 0.065(4) 0.011(4) 0.001(3) 0.006(4) C26 0.108(7) 0.068(5) 0.070(5) -0.016(4) 0.023(5) 0.005(5) C11 0.082(5) 0.089(6) 0.086(5) -0.028(5) 0.050(5) -0.012(5) C10 0.066(5) 0.313(19) 0.045(4) -0.030(7) 0.005(4) 0.002(8) N8 0.145(7) 0.069(4) 0.095(5) -0.032(4) 0.030(5) 0.012(5) C9 0.166(12) 0.083(7) 0.220(15) -0.067(9) -0.101(11) 0.037(8) _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 Zn N3 2.020(4) . ? Zn N1 2.037(4) . ? Zn O3 2.122(4) . ? Zn O1 2.134(4) . ? Zn N6 2.330(5) . ? Zn N5 2.442(5) . ? O3 C16 1.274(6) . ? C16 C15 1.383(8) . ? C16 C17 1.517(7) . ? O1 C2 1.270(6) . ? C19 N4 1.328(6) . ? C19 C18 1.365(8) . ? C19 C20 1.521(8) . ? C2 C1 1.384(7) . ? C2 C3 1.520(7) . ? O4 C20 1.243(7) . ? C18 C17 1.421(7) . ? C18 H18 0.9500 . ? N1 C3 1.292(6) . ? N1 C7 1.453(7) . ? C3 C4 1.415(6) . ? N3 C17 1.299(7) . ? N3 C21 1.454(7) . ? C25 N4 1.446(8) . ? C25 C26 1.505(10) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C21 C22 1.515(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N5 C8 1.425(9) . ? N5 C9 1.434(13) . ? N5 C10 1.468(11) . ? C6 O2 1.240(7) . ? C6 C1 1.406(8) . ? C6 C5 1.521(9) . ? C15 C20 1.411(7) . ? C15 H15 0.9500 . ? N4 HN4 0.8800 . ? N6 C24 1.471(8) . ? N6 C22 1.473(8) . ? N6 C23 1.475(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C7 C8 1.576(10) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C5 N2 1.324(7) . ? C5 C4 1.368(8) . ? C4 H4 0.9500 . ? N2 C11 1.442(10) . ? N2 H2 0.8800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C1 H1 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C26 N8 1.475(11) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C11 C12 1.313(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N8 C28 1.515(9) . ? N8 C27 1.543(9) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C12 N7 1.633(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N7 C14 1.558(9) . ? N7 C13 1.579(9) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9801 . ? C14 H14C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 N3 Zn N1 171.60(18) . . ? N3 Zn O3 77.96(16) . . ? N1 Zn O3 99.37(16) . . ? N3 Zn O1 110.27(17) . . ? N1 Zn O1 77.69(16) . . ? O3 Zn O1 92.98(16) . . ? N3 Zn N6 77.44(17) . . ? N1 Zn N6 106.30(18) . . ? O3 Zn N6 153.61(15) . . ? O1 Zn N6 86.67(17) . . ? N3 Zn N5 95.60(17) . . ? N1 Zn N5 76.34(16) . . ? O3 Zn N5 89.69(17) . . ? O1 Zn N5 153.98(15) . . ? N6 Zn N5 102.07(18) . . ? C16 O3 Zn 113.3(3) . . ? O3 C16 C15 124.5(5) . . ? O3 C16 C17 117.1(5) . . ? C15 C16 C17 118.4(4) . . ? C2 O1 Zn 113.4(3) . . ? N4 C19 C18 126.1(5) . . ? N4 C19 C20 112.9(5) . . ? C18 C19 C20 120.9(4) . . ? O1 C2 C1 124.1(5) . . ? O1 C2 C3 117.3(4) . . ? C1 C2 C3 118.6(5) . . ? C19 C18 C17 120.5(5) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C3 N1 C7 121.6(4) . . ? C3 N1 Zn 118.1(4) . . ? C7 N1 Zn 120.0(3) . . ? N1 C3 C4 127.0(5) . . ? N1 C3 C2 113.4(4) . . ? C4 C3 C2 119.6(4) . . ? C17 N3 C21 121.2(4) . . ? C17 N3 Zn 118.1(4) . . ? C21 N3 Zn 120.1(3) . . ? N3 C17 C18 127.2(5) . . ? N3 C17 C16 113.1(4) . . ? C18 C17 C16 119.7(5) . . ? N4 C25 C26 111.7(6) . . ? N4 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? N4 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 107.9 . . ? N3 C21 C22 108.5(5) . . ? N3 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? N3 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? C8 N5 C9 113.1(8) . . ? C8 N5 C10 110.4(8) . . ? C9 N5 C10 105.0(9) . . ? C8 N5 Zn 98.7(4) . . ? C9 N5 Zn 121.7(6) . . ? C10 N5 Zn 107.7(5) . . ? O2 C6 C1 124.4(6) . . ? O2 C6 C5 118.1(5) . . ? C1 C6 C5 117.5(5) . . ? C16 C15 C20 122.6(5) . . ? C16 C15 H15 118.7 . . ? C20 C15 H15 118.7 . . ? C19 N4 C25 125.4(5) . . ? C19 N4 HN4 117.3 . . ? C25 N4 HN4 117.3 . . ? C24 N6 C22 111.4(5) . . ? C24 N6 C23 108.5(5) . . ? C22 N6 C23 110.3(5) . . ? C24 N6 Zn 113.6(4) . . ? C22 N6 Zn 101.9(4) . . ? C23 N6 Zn 111.1(4) . . ? O4 C20 C15 125.1(6) . . ? O4 C20 C19 117.3(5) . . ? C15 C20 C19 117.7(5) . . ? N6 C22 C21 111.5(5) . . ? N6 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? N6 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? N1 C7 C8 106.7(5) . . ? N1 C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? N1 C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? N2 C5 C4 125.2(6) . . ? N2 C5 C6 113.5(5) . . ? C4 C5 C6 121.3(5) . . ? C5 C4 C3 120.3(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C5 N2 C11 123.7(6) . . ? C5 N2 H2 118.2 . . ? C11 N2 H2 118.2 . . ? N5 C8 C7 109.8(6) . . ? N5 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N5 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C2 C1 C6 122.6(5) . . ? C2 C1 H1 118.7 . . ? C6 C1 H1 118.7 . . ? N6 C24 H24A 109.5 . . ? N6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N6 C23 H23A 109.5 . . ? N6 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N6 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N8 C26 C25 110.1(7) . . ? N8 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? N8 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.2 . . ? C12 C11 N2 109.9(10) . . ? C12 C11 H11A 109.7 . . ? N2 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? N2 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N5 C10 H10A 109.5 . . ? N5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C26 N8 C28 111.6(9) . . ? C26 N8 C27 107.2(10) . . ? C28 N8 C27 104.6(10) . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C12 N7 106.0(12) . . ? C11 C12 H12A 110.5 . . ? N7 C12 H12A 110.5 . . ? C11 C12 H12B 110.5 . . ? N7 C12 H12B 110.5 . . ? H12A C12 H12B 108.7 . . ? C14 N7 C13 115.5(13) . . ? C14 N7 C12 97.8(9) . . ? C13 N7 C12 100.2(9) . . ? N7 C13 H13A 109.5 . . ? N7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 H14A 109.5 . . ? N7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N8 C27 H27A 109.5 . . ? N8 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N8 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N8 C28 H28A 109.5 . . ? N8 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N8 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.965 _refine_diff_density_min -0.996 _refine_diff_density_rms 0.123