# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_2013192_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H N4 O2' _chemical_formula_weight 341.26 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 3.7225(6) _cell_length_b 14.857(3) _cell_length_c 27.524(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1522.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_T_max 0.9950 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6487 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0953 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2210 _reflns_number_gt 1652 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(4) _refine_ls_number_reflns 2210 _refine_ls_number_parameters 244 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.874 _refine_ls_restrained_S_all 1.864 _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 O1 O 0.1528(10) 0.6291(3) 0.04682(11) 0.0164(9) Uani 1 1 d . . . O2 O -0.0492(10) 0.1152(2) 0.17888(12) 0.0154(10) Uani 1 1 d . . . N3 N 0.1900(12) 0.3744(3) 0.22501(16) 0.0169(12) Uani 1 1 d . . . N1 N -0.0142(11) 0.4823(3) 0.06290(14) 0.0152(12) Uani 1 1 d . . . N2 N 0.3339(11) 0.5286(3) 0.20692(16) 0.0146(12) Uani 1 1 d . . . N4 N -0.1149(11) 0.2043(3) 0.24458(14) 0.0170(12) Uani 1 1 d . . . H4A H -0.1877 0.1573 0.2599 0.020 Uiso 1 1 calc R . . H4B H -0.1032 0.2553 0.2593 0.020 Uiso 1 1 calc R . . C13 C 0.1398(14) 0.3550(4) 0.17730(19) 0.0131(14) Uani 1 1 d . . . C20 C 0.2145(14) 0.0713(4) 0.0536(2) 0.0200(16) Uani 1 1 d . . . H20 H 0.2309 0.0255 0.0307 0.024 Uiso 1 1 calc R . . C5 C 0.5437(14) 0.7339(4) 0.15176(19) 0.0159(15) Uani 1 1 d . . . H5 H 0.6044 0.7180 0.1834 0.019 Uiso 1 1 calc R . . C14 C 0.0926(13) 0.2621(4) 0.16501(17) 0.0118(14) Uani 1 1 d U . . C2 C 0.3729(15) 0.7827(4) 0.05575(19) 0.0162(14) Uani 1 1 d . . . H2 H 0.3174 0.7982 0.0239 0.019 Uiso 1 1 calc R . . C9 C -0.0095(14) 0.4183(4) 0.09583(18) 0.0139(14) Uani 1 1 d U . . H9 H -0.1078 0.3629 0.0873 0.017 Uiso 1 1 calc R . . C10 C 0.1331(14) 0.4270(4) 0.14305(17) 0.0091(14) Uani 1 1 d . . . C12 C 0.2782(15) 0.4591(4) 0.23616(18) 0.0195(15) Uani 1 1 d . . . H12 H 0.3044 0.4710 0.2691 0.023 Uiso 1 1 calc R . . C11 C 0.2534(13) 0.5117(4) 0.15914(19) 0.0107(14) Uani 1 1 d . . . C8 C 0.1370(14) 0.5583(4) 0.07858(19) 0.0124(14) Uani 1 1 d . . . C15 C -0.0207(14) 0.1981(4) 0.1983(2) 0.0127(14) Uani 1 1 d . . . C4 C 0.6096(15) 0.8191(4) 0.13452(19) 0.0158(14) Uani 1 1 d . . . H4 H 0.7125 0.8616 0.1551 0.019 Uiso 1 1 calc R . . C6 C 0.3838(15) 0.6720(4) 0.12055(18) 0.0111(14) Uani 1 1 d . . . C7 C 0.2696(14) 0.5796(4) 0.12361(19) 0.0121(14) Uani 1 1 d . . . C19 C 0.3164(14) 0.1578(4) 0.04143(18) 0.0177(15) Uani 1 1 d . . . H19 H 0.4038 0.1691 0.0104 0.021 Uiso 1 1 calc R . . C1 C 0.3063(14) 0.6987(4) 0.0737(2) 0.0146(14) Uani 1 1 d . . . C21 C 0.0883(14) 0.0525(4) 0.09983(19) 0.0160(15) Uani 1 1 d . . . H21 H 0.0228 -0.0053 0.1092 0.019 Uiso 1 1 calc R . . C18 C 0.2918(13) 0.2283(4) 0.07426(16) 0.0138(14) Uani 1 1 d U . . H18 H 0.3648 0.2859 0.0654 0.017 Uiso 1 1 calc R . . C17 C 0.1577(14) 0.2123(4) 0.12028(17) 0.0103(13) Uani 1 1 d U . . C3 C 0.5261(14) 0.8432(4) 0.08728(19) 0.0176(15) Uani 1 1 d . . . H3 H 0.5746 0.9014 0.0767 0.021 Uiso 1 1 calc R . . C16 C 0.0658(14) 0.1239(4) 0.13063(18) 0.0111(14) 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 O1 0.021(2) 0.012(2) 0.015(2) 0.001(2) 0.000(2) -0.002(2) O2 0.022(2) 0.006(2) 0.019(2) -0.0025(18) 0.0017(19) -0.0026(19) N3 0.022(3) 0.003(3) 0.026(3) -0.003(2) 0.000(3) -0.003(3) N1 0.018(3) 0.007(3) 0.020(3) 0.004(2) 0.001(2) 0.001(2) N2 0.018(3) 0.017(3) 0.009(3) 0.002(2) -0.001(2) 0.002(3) N4 0.027(3) 0.010(3) 0.014(3) 0.000(2) 0.005(2) 0.001(3) C13 0.008(3) 0.019(4) 0.012(3) -0.004(3) 0.002(3) -0.003(3) C20 0.021(4) 0.014(4) 0.025(4) -0.010(3) -0.003(3) 0.002(3) C5 0.012(3) 0.021(4) 0.014(3) 0.000(3) 0.001(3) 0.006(3) C14 0.0119(16) 0.0119(16) 0.0118(16) 0.0011(10) -0.0003(10) 0.0003(10) C2 0.017(3) 0.017(4) 0.015(3) -0.002(3) 0.003(3) 0.003(3) C9 0.0140(17) 0.0134(17) 0.0142(17) -0.0008(10) 0.0002(10) 0.0004(10) C10 0.009(3) 0.008(4) 0.011(3) 0.005(3) 0.003(3) 0.002(3) C12 0.027(4) 0.021(4) 0.011(3) 0.002(3) 0.003(3) 0.001(3) C11 0.006(3) 0.007(3) 0.019(4) 0.001(3) 0.001(3) 0.001(3) C8 0.014(3) 0.006(4) 0.018(4) 0.005(3) 0.002(3) 0.000(3) C15 0.013(3) 0.013(4) 0.012(3) -0.003(3) -0.001(3) -0.001(3) C4 0.015(3) 0.010(4) 0.022(4) -0.009(3) 0.000(3) 0.001(3) C6 0.010(3) 0.015(4) 0.008(3) 0.000(3) 0.000(3) 0.002(3) C7 0.010(3) 0.014(4) 0.012(3) -0.002(3) 0.000(3) 0.000(3) C19 0.015(3) 0.027(4) 0.011(3) -0.002(3) 0.002(3) 0.000(3) C1 0.012(3) 0.012(4) 0.019(4) -0.006(3) 0.001(3) 0.000(3) C21 0.014(4) 0.014(4) 0.020(4) 0.002(3) 0.001(3) 0.003(3) C18 0.0137(16) 0.0134(17) 0.0143(16) 0.0005(10) -0.0001(10) -0.0003(10) C17 0.0099(15) 0.0106(16) 0.0104(15) -0.0005(10) -0.0005(10) -0.0002(10) C3 0.023(3) 0.010(4) 0.019(4) 0.003(3) 0.003(3) 0.004(3) C16 0.015(3) 0.015(4) 0.004(3) 0.001(3) 0.001(3) -0.004(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 O1 C8 1.370(6) . ? O1 C1 1.393(6) . ? O2 C15 1.347(6) . ? O2 C16 1.401(5) . ? N3 C12 1.337(7) . ? N3 C13 1.357(5) . ? N1 C9 1.314(6) . ? N1 C8 1.333(6) . ? N2 C12 1.325(6) . ? N2 C11 1.372(6) . ? N4 C15 1.324(5) . ? C13 C10 1.425(7) . ? C13 C14 1.432(7) . ? C20 C19 1.382(7) . ? C20 C21 1.384(6) . ? C5 C4 1.375(7) . ? C5 C6 1.392(7) . ? C14 C15 1.386(7) . ? C14 C17 1.457(6) . ? C2 C1 1.365(7) . ? C2 C3 1.373(7) . ? C9 C10 1.410(6) . ? C10 C11 1.408(7) . ? C11 C7 1.406(7) . ? C8 C7 1.371(6) . ? C4 C3 1.384(6) . ? C6 C1 1.380(6) . ? C6 C7 1.439(7) . ? C19 C18 1.386(7) . ? C21 C16 1.361(7) . ? C18 C17 1.382(6) . ? C17 C16 1.386(7) . ? 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 C8 O1 C1 104.4(4) . . ? C15 O2 C16 105.5(4) . . ? C12 N3 C13 117.1(4) . . ? C9 N1 C8 112.6(5) . . ? C12 N2 C11 113.9(5) . . ? N3 C13 C10 118.9(5) . . ? N3 C13 C14 116.7(5) . . ? C10 C13 C14 124.4(5) . . ? C19 C20 C21 120.2(5) . . ? C4 C5 C6 118.2(5) . . ? C15 C14 C13 122.8(5) . . ? C15 C14 C17 105.1(5) . . ? C13 C14 C17 132.0(5) . . ? C1 C2 C3 116.4(5) . . ? N1 C9 C10 125.1(5) . . ? C11 C10 C9 119.4(5) . . ? C11 C10 C13 117.2(5) . . ? C9 C10 C13 123.2(5) . . ? N2 C12 N3 129.2(5) . . ? N2 C11 C7 121.8(5) . . ? N2 C11 C10 122.3(5) . . ? C7 C11 C10 115.9(5) . . ? N1 C8 O1 117.5(5) . . ? N1 C8 C7 129.8(5) . . ? O1 C8 C7 112.6(5) . . ? N4 C15 O2 115.1(5) . . ? N4 C15 C14 132.0(5) . . ? O2 C15 C14 112.9(5) . . ? C5 C4 C3 121.5(5) . . ? C1 C6 C5 118.5(5) . . ? C1 C6 C7 105.5(5) . . ? C5 C6 C7 136.0(5) . . ? C8 C7 C11 116.6(5) . . ? C8 C7 C6 105.9(5) . . ? C11 C7 C6 137.5(5) . . ? C20 C19 C18 121.8(5) . . ? C2 C1 C6 124.2(5) . . ? C2 C1 O1 124.1(5) . . ? C6 C1 O1 111.6(5) . . ? C16 C21 C20 115.9(6) . . ? C17 C18 C19 119.4(5) . . ? C18 C17 C16 116.2(5) . . ? C18 C17 C14 138.3(5) . . ? C16 C17 C14 105.4(4) . . ? C2 C3 C4 121.2(5) . . ? C21 C16 C17 126.5(5) . . ? C21 C16 O2 122.5(5) . . ? C17 C16 O2 111.0(4) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.420 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 945367' ####################################################################### # # 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_2013184_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H34 N8 O8' _chemical_formula_weight 826.81 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8285(15) _cell_length_b 21.348(8) _cell_length_c 22.566(10) _cell_angle_alpha 78.70(3) _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1808.7(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14771 _diffrn_reflns_av_R_equivalents 0.3143 _diffrn_reflns_av_sigmaI/netI 0.5748 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 0.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6239 _reflns_number_gt 1246 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6239 _refine_ls_number_parameters 564 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3507 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 0.759 _refine_ls_restrained_S_all 0.759 _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 O1' O 0.8929(18) 0.6386(4) 1.1516(3) 0.060(2) Uani 1 1 d . . . O4' O 1.2157(16) 0.9480(3) 0.5911(3) 0.052(2) Uani 1 1 d . . . O2' O 1.0211(15) 0.7205(3) 1.0298(3) 0.0424(19) Uani 1 1 d . . . O3' O 1.2273(16) 0.9951(3) 0.6977(3) 0.0424(18) Uani 1 1 d . . . O4 O 0.7223(17) 0.5514(3) 0.9096(3) 0.055(2) Uani 1 1 d . . . O1 O 0.3968(18) 0.8607(4) 0.3491(3) 0.057(2) Uani 1 1 d . . . O2 O 0.5209(15) 0.7794(3) 0.4706(3) 0.0416(18) Uani 1 1 d . . . O3 O 0.7213(16) 0.5049(3) 0.8018(3) 0.0468(19) Uani 1 1 d . . . N1' N 1.1602(19) 0.7696(4) 0.9306(4) 0.038(2) Uani 1 1 d . . . N2' N 0.7612(19) 0.9384(4) 0.9755(4) 0.043(2) Uani 1 1 d . . . N3' N 0.908(2) 0.9948(4) 0.8740(4) 0.044(2) Uani 1 1 d . . . N4' N 1.2497(19) 1.0579(4) 0.7667(4) 0.056(3) Uani 1 1 d . . . H4'1 H 1.3251 1.0871 0.7377 0.067 Uiso 1 1 calc R . . H4'2 H 1.2242 1.0661 0.8023 0.067 Uiso 1 1 calc R . . N1 N 0.6574(19) 0.7304(4) 0.5694(4) 0.041(2) Uani 1 1 d . . . N2 N 0.2588(19) 0.5607(4) 0.5252(4) 0.038(2) Uani 1 1 d . . . N3 N 0.401(2) 0.5053(4) 0.6254(4) 0.046(2) Uani 1 1 d . . . N4 N 0.750(2) 0.4406(4) 0.7330(4) 0.060(3) Uani 1 1 d . . . H4A H 0.8189 0.4113 0.7624 0.072 Uiso 1 1 calc R . . H4B H 0.7292 0.4324 0.6974 0.072 Uiso 1 1 calc R . . C23' C 0.784(3) 0.6000(6) 1.1099(5) 0.068(4) Uani 1 1 d . . . H17 H 0.5776 0.6182 1.0891 0.102 Uiso 1 1 calc R . . H3 H 0.7335 0.5576 1.1315 0.102 Uiso 1 1 calc R . . H1 H 0.9666 0.5984 1.0812 0.102 Uiso 1 1 calc R . . C17' C 0.817(3) 0.7025(6) 1.1342(5) 0.044(3) Uani 1 1 d . . . C16' C 0.869(2) 0.7403(5) 1.0797(4) 0.039(3) Uani 1 1 d . . . C21' C 0.793(2) 0.8056(5) 1.0646(5) 0.032(3) Uani 1 1 d . . . C13' C 0.885(2) 0.8270(5) 1.0020(4) 0.033(3) Uani 1 1 d . . . C14' C 0.869(2) 0.8840(5) 0.9589(4) 0.036(3) Uani 1 1 d . . . C10' C 0.992(2) 0.8812(5) 0.9008(4) 0.029(2) Uani 1 1 d . . . C9' C 0.978(2) 0.9388(5) 0.8567(4) 0.037(3) Uani 1 1 d . . . C7' C 1.045(2) 0.9450(5) 0.7938(4) 0.030(2) Uani 1 1 d . . . C6' C 0.994(2) 0.9006(4) 0.7527(4) 0.030(2) Uani 1 1 d . . . C1' C 1.109(2) 0.9327(5) 0.6965(5) 0.031(3) Uani 1 1 d . . . C2' C 1.100(2) 0.9102(5) 0.6429(5) 0.036(3) Uani 1 1 d . . . C22' C 1.208(3) 0.9215(6) 0.5365(5) 0.072(4) Uani 1 1 d . . . H4 H 1.3789 0.8881 0.5396 0.108 Uiso 1 1 calc R . . H5 H 1.2612 0.9545 0.5022 0.108 Uiso 1 1 calc R . . H2 H 0.9805 0.9045 0.5317 0.108 Uiso 1 1 calc R . . C12' C 1.021(2) 0.7739(5) 0.9832(5) 0.035(3) Uani 1 1 d . . . C11' C 1.143(2) 0.8249(5) 0.8891(4) 0.037(3) Uani 1 1 d . . . H16 H 1.2360 0.8255 0.8509 0.044 Uiso 1 1 calc R . . C15' C 0.797(2) 0.9897(5) 0.9322(5) 0.049(3) Uani 1 1 d . . . H12 H 0.7371 1.0281 0.9432 0.059 Uiso 1 1 calc R . . C5' C 0.850(2) 0.8403(4) 0.7557(4) 0.037(3) Uani 1 1 d . . . H11 H 0.7649 0.8170 0.7919 0.045 Uiso 1 1 calc R . . C4' C 0.837(2) 0.8161(5) 0.7042(5) 0.043(3) Uani 1 1 d . . . H10 H 0.7424 0.7755 0.7066 0.051 Uiso 1 1 calc R . . C3' C 0.957(2) 0.8484(5) 0.6482(5) 0.042(3) Uani 1 1 d . . . H9 H 0.9431 0.8294 0.6145 0.050 Uiso 1 1 calc R . . C8' C 1.171(2) 0.9994(5) 0.7564(5) 0.039(3) Uani 1 1 d . . . C20' C 0.646(2) 0.8344(5) 1.1094(5) 0.046(3) Uani 1 1 d . . . H15 H 0.5895 0.8776 1.1012 0.055 Uiso 1 1 calc R . . C19' C 0.587(2) 0.7977(5) 1.1654(4) 0.047(3) Uani 1 1 d . . . H14 H 0.4917 0.8165 1.1956 0.056 Uiso 1 1 calc R . . C18' C 0.669(3) 0.7315(6) 1.1784(5) 0.058(4) Uani 1 1 d . . . H13 H 0.6226 0.7074 1.2166 0.070 Uiso 1 1 calc R . . C22 C 0.712(3) 0.5789(6) 0.9626(5) 0.070(4) Uani 1 1 d . . . H22 H 0.8482 0.6174 0.9560 0.105 Uiso 1 1 calc R . . H21 H 0.8064 0.5490 0.9962 0.105 Uiso 1 1 calc R . . H18 H 0.4747 0.5886 0.9711 0.105 Uiso 1 1 calc R . . C2 C 0.599(2) 0.5892(5) 0.8568(5) 0.035(3) Uani 1 1 d . . . C1 C 0.606(2) 0.5677(5) 0.8043(5) 0.040(3) Uani 1 1 d . . . C6 C 0.498(3) 0.5986(4) 0.7478(5) 0.038(3) Uani 1 1 d . . . C7 C 0.548(2) 0.5557(4) 0.7061(4) 0.029(2) Uani 1 1 d . . . C9 C 0.482(2) 0.5603(5) 0.6438(4) 0.040(3) Uani 1 1 d . . . C10 C 0.494(2) 0.6182(5) 0.6000(4) 0.033(3) Uani 1 1 d . . . C14 C 0.370(2) 0.6159(5) 0.5407(5) 0.036(3) Uani 1 1 d . . . C13 C 0.385(2) 0.6722(5) 0.4978(4) 0.034(3) Uani 1 1 d . . . C21 C 0.293(2) 0.6943(5) 0.4356(5) 0.036(3) Uani 1 1 d . . . C16 C 0.370(2) 0.7585(5) 0.4213(5) 0.043(3) Uani 1 1 d . . . C17 C 0.309(3) 0.7973(5) 0.3655(5) 0.044(3) Uani 1 1 d . . . C23 C 0.279(3) 0.9003(5) 0.3899(5) 0.066(4) Uani 1 1 d . . . H20 H 0.0308 0.8959 0.3952 0.098 Uiso 1 1 calc R . . H19 H 0.3348 0.9441 0.3734 0.098 Uiso 1 1 calc R . . H34 H 0.3929 0.8874 0.4282 0.098 Uiso 1 1 calc R . . C12 C 0.520(2) 0.7250(5) 0.5162(4) 0.036(3) Uani 1 1 d . . . C11 C 0.642(2) 0.6761(5) 0.6104(5) 0.044(3) Uani 1 1 d . . . H33 H 0.7341 0.6762 0.6485 0.053 Uiso 1 1 calc R . . C15 C 0.299(2) 0.5096(5) 0.5674(5) 0.048(3) Uani 1 1 d . . . H29 H 0.2510 0.4710 0.5558 0.057 Uiso 1 1 calc R . . C8 C 0.675(2) 0.4997(5) 0.7429(5) 0.041(3) Uani 1 1 d . . . C5 C 0.351(2) 0.6599(5) 0.7438(5) 0.044(3) Uani 1 1 d . . . H25 H 0.2672 0.6829 0.7072 0.052 Uiso 1 1 calc R . . C4 C 0.335(2) 0.6845(5) 0.7959(4) 0.040(3) Uani 1 1 d . . . H24 H 0.2384 0.7249 0.7940 0.048 Uiso 1 1 calc R . . C3 C 0.460(2) 0.6508(5) 0.8521(4) 0.044(3) Uani 1 1 d . . . H23 H 0.4510 0.6695 0.8860 0.053 Uiso 1 1 calc R . . C20 C 0.147(2) 0.6649(5) 0.3909(5) 0.043(3) Uani 1 1 d . . . H32 H 0.0892 0.6218 0.3987 0.051 Uiso 1 1 calc R . . C19 C 0.091(2) 0.7040(6) 0.3334(5) 0.053(3) Uani 1 1 d . . . H31 H -0.0014 0.6857 0.3027 0.063 Uiso 1 1 calc R . . C18 C 0.169(3) 0.7684(6) 0.3213(5) 0.056(3) Uani 1 1 d . . . H30 H 0.1263 0.7926 0.2830 0.068 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 O1' 0.081(6) 0.050(6) 0.048(5) -0.010(4) -0.011(4) 0.009(5) O4' 0.072(6) 0.051(5) 0.034(5) -0.009(4) 0.003(4) -0.008(4) O2' 0.049(5) 0.041(5) 0.035(4) -0.002(4) 0.000(4) 0.006(4) O3' 0.065(5) 0.031(5) 0.032(4) -0.007(4) -0.002(4) -0.001(4) O4 0.077(6) 0.062(5) 0.023(4) -0.004(4) -0.010(4) 0.010(4) O1 0.079(6) 0.050(6) 0.042(5) -0.008(4) 0.001(4) -0.003(5) O2 0.056(5) 0.036(5) 0.033(4) -0.008(4) -0.005(4) -0.005(4) O3 0.064(5) 0.042(5) 0.036(5) -0.011(4) -0.009(4) 0.007(4) N1' 0.047(6) 0.040(6) 0.027(5) -0.006(5) -0.003(5) 0.012(5) N2' 0.052(6) 0.041(6) 0.037(6) -0.006(5) -0.009(5) 0.000(5) N3' 0.060(7) 0.045(6) 0.030(5) -0.016(5) -0.003(5) 0.007(5) N4' 0.084(7) 0.040(6) 0.045(6) -0.010(5) -0.002(5) -0.008(5) N1 0.043(6) 0.050(6) 0.032(6) -0.016(5) -0.009(5) -0.009(5) N2 0.044(6) 0.031(6) 0.037(6) -0.001(5) -0.004(5) -0.011(5) N3 0.061(6) 0.037(6) 0.042(6) -0.016(5) -0.006(5) 0.001(5) N4 0.107(8) 0.030(6) 0.047(6) -0.017(5) -0.012(5) 0.018(5) C23' 0.074(9) 0.059(9) 0.072(9) -0.017(8) -0.014(7) 0.005(7) C17' 0.035(8) 0.047(8) 0.049(8) -0.008(7) 0.009(6) -0.005(6) C16' 0.044(8) 0.046(8) 0.023(6) 0.003(6) 0.014(6) -0.006(6) C21' 0.019(6) 0.032(7) 0.047(7) -0.010(6) 0.014(6) -0.006(5) C13' 0.034(7) 0.033(7) 0.031(6) -0.009(6) 0.003(5) -0.013(6) C14' 0.046(8) 0.027(7) 0.035(7) -0.007(6) -0.006(6) -0.011(6) C10' 0.031(7) 0.033(7) 0.024(6) -0.007(5) -0.002(5) -0.004(5) C9' 0.026(7) 0.046(7) 0.041(7) -0.016(6) 0.001(6) 0.003(6) C7' 0.024(6) 0.032(7) 0.032(6) -0.002(5) 0.009(5) -0.008(5) C6' 0.021(6) 0.027(6) 0.040(7) -0.005(6) 0.005(5) -0.002(5) C1' 0.025(7) 0.029(7) 0.040(7) -0.006(6) 0.011(6) 0.000(5) C2' 0.025(7) 0.045(8) 0.039(7) -0.011(6) 0.006(6) 0.000(6) C22' 0.082(9) 0.095(11) 0.043(8) -0.026(8) 0.006(7) -0.011(7) C12' 0.032(7) 0.034(7) 0.037(7) -0.004(6) -0.007(6) -0.006(6) C11' 0.034(7) 0.050(8) 0.028(6) -0.011(6) 0.006(5) 0.006(6) C15' 0.051(8) 0.042(8) 0.060(9) -0.025(7) -0.005(7) 0.009(6) C5' 0.043(7) 0.036(7) 0.034(7) -0.010(6) -0.007(6) 0.008(5) C4' 0.030(7) 0.036(7) 0.060(8) -0.006(6) -0.002(6) -0.006(5) C3' 0.037(7) 0.053(8) 0.039(7) -0.017(6) -0.007(6) -0.007(6) C8' 0.046(8) 0.038(7) 0.037(7) -0.016(6) -0.005(6) -0.003(6) C20' 0.042(8) 0.054(8) 0.045(7) -0.018(7) 0.002(6) 0.007(6) C19' 0.050(8) 0.063(9) 0.030(7) -0.015(6) -0.001(6) 0.014(7) C18' 0.044(8) 0.083(11) 0.043(8) 0.001(8) -0.013(6) -0.002(7) C22 0.073(9) 0.108(11) 0.031(7) -0.016(8) -0.007(6) 0.010(7) C2 0.030(7) 0.031(7) 0.046(7) -0.011(6) 0.008(6) -0.003(5) C1 0.047(8) 0.031(7) 0.044(7) -0.012(6) -0.002(6) 0.005(6) C6 0.044(7) 0.025(6) 0.043(7) -0.004(6) -0.006(6) -0.002(6) C7 0.027(6) 0.024(6) 0.033(6) 0.001(5) 0.006(5) -0.012(5) C9 0.048(8) 0.033(7) 0.040(7) -0.014(6) -0.008(6) 0.005(6) C10 0.032(7) 0.035(7) 0.032(6) -0.009(6) -0.006(5) -0.005(5) C14 0.032(7) 0.036(7) 0.037(7) -0.001(6) 0.009(6) -0.013(6) C13 0.038(7) 0.038(7) 0.029(6) -0.011(6) 0.001(5) -0.008(6) C21 0.034(7) 0.036(7) 0.039(7) -0.007(6) -0.003(6) -0.001(6) C16 0.038(7) 0.055(9) 0.035(7) -0.009(7) -0.005(6) 0.002(6) C17 0.052(8) 0.047(8) 0.035(7) -0.008(7) 0.006(6) 0.002(6) C23 0.077(9) 0.054(8) 0.066(9) -0.013(7) -0.001(7) 0.013(7) C12 0.030(7) 0.037(7) 0.038(7) 0.002(6) -0.005(6) -0.002(6) C11 0.041(7) 0.057(9) 0.036(7) -0.014(7) 0.000(6) 0.005(6) C15 0.056(8) 0.046(8) 0.044(8) -0.019(7) 0.001(6) -0.005(6) C8 0.052(8) 0.034(7) 0.039(7) -0.012(6) 0.005(6) -0.006(6) C5 0.037(7) 0.057(8) 0.039(7) -0.015(6) -0.002(6) 0.000(6) C4 0.042(7) 0.043(7) 0.038(7) -0.016(6) -0.004(6) 0.008(6) C3 0.042(7) 0.058(8) 0.033(7) -0.012(6) 0.002(6) -0.013(6) C20 0.040(7) 0.042(7) 0.044(7) -0.003(6) 0.001(6) -0.007(6) C19 0.045(7) 0.075(9) 0.038(7) -0.007(7) -0.020(6) -0.004(7) C18 0.062(9) 0.068(10) 0.036(8) -0.004(7) -0.001(6) 0.011(7) _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 O1' C17' 1.374(11) . ? O1' C23' 1.428(12) . ? O4' C2' 1.360(10) . ? O4' C22' 1.452(11) . ? O2' C12' 1.389(10) . ? O2' C16' 1.405(10) . ? O3' C8' 1.361(11) . ? O3' C1' 1.412(10) . ? O4 C2 1.384(11) . ? O4 C22 1.431(11) . ? O1 C17 1.372(11) . ? O1 C23 1.440(11) . ? O2 C12 1.393(10) . ? O2 C16 1.402(11) . ? O3 C8 1.368(11) . ? O3 C1 1.424(10) . ? N1' C12' 1.321(11) . ? N1' C11' 1.356(10) . ? N2' C15' 1.324(12) . ? N2' C14' 1.353(11) . ? N3' C9' 1.356(11) . ? N3' C15' 1.365(12) . ? N4' C8' 1.350(12) . ? N4' H4'1 0.8600 . ? N4' H4'2 0.8600 . ? N1 C11 1.334(11) . ? N1 C12 1.337(11) . ? N2 C15 1.309(11) . ? N2 C14 1.360(12) . ? N3 C15 1.352(12) . ? N3 C9 1.356(11) . ? N4 C8 1.353(11) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? C23' H17 0.9600 . ? C23' H3 0.9600 . ? C23' H1 0.9600 . ? C17' C16' 1.349(13) . ? C17' C18' 1.393(13) . ? C16' C21' 1.398(12) . ? C21' C20' 1.400(12) . ? C21' C13' 1.440(12) . ? C13' C12' 1.388(11) . ? C13' C14' 1.401(12) . ? C14' C10' 1.406(11) . ? C10' C11' 1.406(11) . ? C10' C9' 1.422(11) . ? C9' C7' 1.423(12) . ? C7' C8' 1.383(12) . ? C7' C6' 1.463(12) . ? C6' C1' 1.390(11) . ? C6' C5' 1.390(12) . ? C1' C2' 1.385(13) . ? C2' C3' 1.412(12) . ? C22' H4 0.9600 . ? C22' H5 0.9600 . ? C22' H2 0.9600 . ? C11' H16 0.9300 . ? C15' H12 0.9300 . ? C5' C4' 1.361(12) . ? C5' H11 0.9300 . ? C4' C3' 1.394(12) . ? C4' H10 0.9300 . ? C3' H9 0.9300 . ? C20' C19' 1.370(12) . ? C20' H15 0.9300 . ? C19' C18' 1.421(13) . ? C19' H14 0.9300 . ? C18' H13 0.9300 . ? C22 H22 0.9600 . ? C22 H21 0.9600 . ? C22 H18 0.9600 . ? C2 C1 1.352(13) . ? C2 C3 1.402(11) . ? C1 C6 1.378(12) . ? C6 C5 1.411(11) . ? C6 C7 1.448(12) . ? C7 C8 1.402(12) . ? C7 C9 1.414(12) . ? C9 C10 1.424(12) . ? C10 C11 1.420(13) . ? C10 C14 1.430(12) . ? C14 C13 1.390(12) . ? C13 C12 1.376(12) . ? C13 C21 1.434(13) . ? C21 C16 1.377(13) . ? C21 C20 1.406(13) . ? C16 C17 1.384(13) . ? C17 C18 1.380(14) . ? C23 H20 0.9600 . ? C23 H19 0.9600 . ? C23 H34 0.9600 . ? C11 H33 0.9300 . ? C15 H29 0.9300 . ? C5 C4 1.381(12) . ? C5 H25 0.9300 . ? C4 C3 1.414(12) . ? C4 H24 0.9300 . ? C3 H23 0.9300 . ? C20 C19 1.413(12) . ? C20 H32 0.9300 . ? C19 C18 1.382(13) . ? C19 H31 0.9300 . ? C18 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 C17' O1' C23' 114.7(8) . . ? C2' O4' C22' 117.3(8) . . ? C12' O2' C16' 106.0(7) . . ? C8' O3' C1' 102.3(8) . . ? C2 O4 C22 116.4(8) . . ? C17 O1 C23 115.0(8) . . ? C12 O2 C16 103.6(7) . . ? C8 O3 C1 104.8(7) . . ? C12' N1' C11' 113.5(8) . . ? C15' N2' C14' 113.3(9) . . ? C9' N3' C15' 115.4(9) . . ? C8' N4' H4'1 120.0 . . ? C8' N4' H4'2 120.0 . . ? H4'1 N4' H4'2 120.0 . . ? C11 N1 C12 112.9(9) . . ? C15 N2 C14 114.6(9) . . ? C15 N3 C9 117.6(9) . . ? C8 N4 H4A 120.0 . . ? C8 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? O1' C23' H17 109.5 . . ? O1' C23' H3 109.5 . . ? H17 C23' H3 109.5 . . ? O1' C23' H1 109.5 . . ? H17 C23' H1 109.5 . . ? H3 C23' H1 109.5 . . ? C16' C17' O1' 127.8(10) . . ? C16' C17' C18' 116.2(11) . . ? O1' C17' C18' 116.0(10) . . ? C17' C16' C21' 125.6(10) . . ? C17' C16' O2' 124.9(10) . . ? C21' C16' O2' 109.4(9) . . ? C16' C21' C20' 117.7(10) . . ? C16' C21' C13' 107.4(9) . . ? C20' C21' C13' 134.9(10) . . ? C12' C13' C14' 117.0(9) . . ? C12' C13' C21' 105.6(9) . . ? C14' C13' C21' 137.3(10) . . ? N2' C14' C13' 119.8(9) . . ? N2' C14' C10' 123.7(9) . . ? C13' C14' C10' 116.4(9) . . ? C14' C10' C11' 120.4(9) . . ? C14' C10' C9' 116.9(9) . . ? C11' C10' C9' 122.5(9) . . ? N3' C9' C10' 119.7(9) . . ? N3' C9' C7' 114.0(9) . . ? C10' C9' C7' 126.2(9) . . ? C8' C7' C9' 125.1(10) . . ? C8' C7' C6' 103.3(8) . . ? C9' C7' C6' 131.6(9) . . ? C1' C6' C5' 117.2(9) . . ? C1' C6' C7' 105.8(8) . . ? C5' C6' C7' 136.9(10) . . ? C2' C1' C6' 126.4(10) . . ? C2' C1' O3' 121.1(9) . . ? C6' C1' O3' 112.4(9) . . ? O4' C2' C1' 119.5(10) . . ? O4' C2' C3' 125.9(10) . . ? C1' C2' C3' 114.6(10) . . ? O4' C22' H4 109.5 . . ? O4' C22' H5 109.5 . . ? H4 C22' H5 109.5 . . ? O4' C22' H2 109.5 . . ? H4 C22' H2 109.5 . . ? H5 C22' H2 109.5 . . ? N1' C12' C13' 129.0(9) . . ? N1' C12' O2' 119.3(9) . . ? C13' C12' O2' 111.5(8) . . ? N1' C11' C10' 123.4(8) . . ? N1' C11' H16 118.3 . . ? C10' C11' H16 118.3 . . ? N2' C15' N3' 129.9(10) . . ? N2' C15' H12 115.0 . . ? N3' C15' H12 115.0 . . ? C4' C5' C6' 118.4(10) . . ? C4' C5' H11 120.8 . . ? C6' C5' H11 120.8 . . ? C5' C4' C3' 124.0(10) . . ? C5' C4' H10 118.0 . . ? C3' C4' H10 118.0 . . ? C4' C3' C2' 119.4(10) . . ? C4' C3' H9 120.3 . . ? C2' C3' H9 120.3 . . ? N4' C8' O3' 112.0(10) . . ? N4' C8' C7' 131.9(10) . . ? O3' C8' C7' 116.1(9) . . ? C19' C20' C21' 118.7(10) . . ? C19' C20' H15 120.7 . . ? C21' C20' H15 120.7 . . ? C20' C19' C18' 121.4(10) . . ? C20' C19' H14 119.3 . . ? C18' C19' H14 119.3 . . ? C17' C18' C19' 120.4(11) . . ? C17' C18' H13 119.8 . . ? C19' C18' H13 119.8 . . ? O4 C22 H22 109.5 . . ? O4 C22 H21 109.5 . . ? H22 C22 H21 109.5 . . ? O4 C22 H18 109.5 . . ? H22 C22 H18 109.5 . . ? H21 C22 H18 109.5 . . ? C1 C2 O4 120.4(9) . . ? C1 C2 C3 114.5(10) . . ? O4 C2 C3 125.0(9) . . ? C2 C1 C6 128.4(10) . . ? C2 C1 O3 121.7(9) . . ? C6 C1 O3 109.8(9) . . ? C1 C6 C5 116.6(10) . . ? C1 C6 C7 108.2(8) . . ? C5 C6 C7 135.0(9) . . ? C8 C7 C9 122.3(9) . . ? C8 C7 C6 103.7(9) . . ? C9 C7 C6 133.9(9) . . ? N3 C9 C7 116.8(9) . . ? N3 C9 C10 118.8(9) . . ? C7 C9 C10 124.5(9) . . ? C11 C10 C9 124.4(9) . . ? C11 C10 C14 118.5(9) . . ? C9 C10 C14 117.0(9) . . ? N2 C14 C13 120.5(10) . . ? N2 C14 C10 122.4(9) . . ? C13 C14 C10 117.0(10) . . ? C12 C13 C14 117.0(9) . . ? C12 C13 C21 104.8(9) . . ? C14 C13 C21 138.2(10) . . ? C16 C21 C20 118.8(10) . . ? C16 C21 C13 107.4(10) . . ? C20 C21 C13 133.9(10) . . ? C21 C16 C17 124.6(11) . . ? C21 C16 O2 111.1(9) . . ? C17 C16 O2 124.4(10) . . ? O1 C17 C18 117.1(10) . . ? O1 C17 C16 125.9(11) . . ? C18 C17 C16 116.8(11) . . ? O1 C23 H20 109.5 . . ? O1 C23 H19 109.5 . . ? H20 C23 H19 109.5 . . ? O1 C23 H34 109.5 . . ? H20 C23 H34 109.5 . . ? H19 C23 H34 109.5 . . ? N1 C12 C13 129.7(10) . . ? N1 C12 O2 117.1(9) . . ? C13 C12 O2 113.1(9) . . ? N1 C11 C10 124.8(9) . . ? N1 C11 H33 117.6 . . ? C10 C11 H33 117.6 . . ? N2 C15 N3 128.9(10) . . ? N2 C15 H29 115.6 . . ? N3 C15 H29 115.6 . . ? N4 C8 O3 112.8(9) . . ? N4 C8 C7 133.7(10) . . ? O3 C8 C7 113.4(9) . . ? C4 C5 C6 117.8(10) . . ? C4 C5 H25 121.1 . . ? C6 C5 H25 121.1 . . ? C5 C4 C3 122.5(9) . . ? C5 C4 H24 118.8 . . ? C3 C4 H24 118.8 . . ? C2 C3 C4 120.1(10) . . ? C2 C3 H23 119.9 . . ? C4 C3 H23 119.9 . . ? C21 C20 C19 116.9(10) . . ? C21 C20 H32 121.5 . . ? C19 C20 H32 121.5 . . ? C18 C19 C20 122.3(11) . . ? C18 C19 H31 118.9 . . ? C20 C19 H31 118.9 . . ? C17 C18 C19 120.7(10) . . ? C17 C18 H30 119.7 . . ? C19 C18 H30 119.7 . . ? 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 C23' O1' C17' C16' -46.5(15) . . . . ? C23' O1' C17' C18' 133.6(10) . . . . ? O1' C17' C16' C21' -178.5(10) . . . . ? C18' C17' C16' C21' 1.5(16) . . . . ? O1' C17' C16' O2' -1.4(18) . . . . ? C18' C17' C16' O2' 178.6(9) . . . . ? C12' O2' C16' C17' 179.6(10) . . . . ? C12' O2' C16' C21' -2.9(10) . . . . ? C17' C16' C21' C20' -1.2(16) . . . . ? O2' C16' C21' C20' -178.7(8) . . . . ? C17' C16' C21' C13' -179.4(10) . . . . ? O2' C16' C21' C13' 3.1(11) . . . . ? C16' C21' C13' C12' -2.0(11) . . . . ? C20' C21' C13' C12' -179.8(11) . . . . ? C16' C21' C13' C14' 177.9(11) . . . . ? C20' C21' C13' C14' 0(2) . . . . ? C15' N2' C14' C13' 172.8(9) . . . . ? C15' N2' C14' C10' -2.8(14) . . . . ? C12' C13' C14' N2' -175.5(9) . . . . ? C21' C13' C14' N2' 4.6(18) . . . . ? C12' C13' C14' C10' 0.5(13) . . . . ? C21' C13' C14' C10' -179.5(11) . . . . ? N2' C14' C10' C11' 171.6(9) . . . . ? C13' C14' C10' C11' -4.2(14) . . . . ? N2' C14' C10' C9' -4.3(14) . . . . ? C13' C14' C10' C9' 180.0(9) . . . . ? C15' N3' C9' C10' -10.7(14) . . . . ? C15' N3' C9' C7' 171.6(8) . . . . ? C14' C10' C9' N3' 11.3(14) . . . . ? C11' C10' C9' N3' -164.4(9) . . . . ? C14' C10' C9' C7' -171.3(9) . . . . ? C11' C10' C9' C7' 13.0(15) . . . . ? N3' C9' C7' C8' 25.9(14) . . . . ? C10' C9' C7' C8' -151.7(10) . . . . ? N3' C9' C7' C6' -151.9(10) . . . . ? C10' C9' C7' C6' 30.6(16) . . . . ? C8' C7' C6' C1' 2.4(10) . . . . ? C9' C7' C6' C1' -179.4(10) . . . . ? C8' C7' C6' C5' -173.1(10) . . . . ? C9' C7' C6' C5' 5.0(19) . . . . ? C5' C6' C1' C2' -1.0(14) . . . . ? C7' C6' C1' C2' -177.6(9) . . . . ? C5' C6' C1' O3' 175.7(7) . . . . ? C7' C6' C1' O3' -0.8(10) . . . . ? C8' O3' C1' C2' 175.8(9) . . . . ? C8' O3' C1' C6' -1.2(10) . . . . ? C22' O4' C2' C1' 178.5(9) . . . . ? C22' O4' C2' C3' -3.3(13) . . . . ? C6' C1' C2' O4' 178.4(8) . . . . ? O3' C1' C2' O4' 2.0(14) . . . . ? C6' C1' C2' C3' 0.0(14) . . . . ? O3' C1' C2' C3' -176.4(8) . . . . ? C11' N1' C12' C13' -4.3(15) . . . . ? C11' N1' C12' O2' 179.8(8) . . . . ? C14' C13' C12' N1' 4.2(15) . . . . ? C21' C13' C12' N1' -175.9(10) . . . . ? C14' C13' C12' O2' -179.7(8) . . . . ? C21' C13' C12' O2' 0.2(11) . . . . ? C16' O2' C12' N1' 178.2(9) . . . . ? C16' O2' C12' C13' 1.6(10) . . . . ? C12' N1' C11' C10' 0.0(14) . . . . ? C14' C10' C11' N1' 4.2(14) . . . . ? C9' C10' C11' N1' 179.8(9) . . . . ? C14' N2' C15' N3' 3.6(15) . . . . ? C9' N3' C15' N2' 3.3(16) . . . . ? C1' C6' C5' C4' 1.2(12) . . . . ? C7' C6' C5' C4' 176.4(10) . . . . ? C6' C5' C4' C3' -0.6(14) . . . . ? C5' C4' C3' C2' -0.4(14) . . . . ? O4' C2' C3' C4' -177.6(8) . . . . ? C1' C2' C3' C4' 0.7(13) . . . . ? C1' O3' C8' N4' -176.4(8) . . . . ? C1' O3' C8' C7' 3.0(10) . . . . ? C9' C7' C8' N4' -2.5(17) . . . . ? C6' C7' C8' N4' 175.7(10) . . . . ? C9' C7' C8' O3' 178.2(9) . . . . ? C6' C7' C8' O3' -3.5(11) . . . . ? C16' C21' C20' C19' 0.7(15) . . . . ? C13' C21' C20' C19' 178.3(11) . . . . ? C21' C20' C19' C18' -0.7(16) . . . . ? C16' C17' C18' C19' -1.4(15) . . . . ? O1' C17' C18' C19' 178.6(9) . . . . ? C20' C19' C18' C17' 1.0(16) . . . . ? C22 O4 C2 C1 178.6(10) . . . . ? C22 O4 C2 C3 -1.5(14) . . . . ? O4 C2 C1 C6 -179.4(10) . . . . ? C3 C2 C1 C6 0.7(17) . . . . ? O4 C2 C1 O3 3.3(16) . . . . ? C3 C2 C1 O3 -176.7(8) . . . . ? C8 O3 C1 C2 177.1(10) . . . . ? C8 O3 C1 C6 -0.6(11) . . . . ? C2 C1 C6 C5 -2.2(17) . . . . ? O3 C1 C6 C5 175.4(8) . . . . ? C2 C1 C6 C7 -178.6(11) . . . . ? O3 C1 C6 C7 -1.0(12) . . . . ? C1 C6 C7 C8 2.2(11) . . . . ? C5 C6 C7 C8 -173.2(11) . . . . ? C1 C6 C7 C9 178.8(11) . . . . ? C5 C6 C7 C9 3(2) . . . . ? C15 N3 C9 C7 172.8(8) . . . . ? C15 N3 C9 C10 -7.0(14) . . . . ? C8 C7 C9 N3 27.2(14) . . . . ? C6 C7 C9 N3 -149.0(11) . . . . ? C8 C7 C9 C10 -153.0(9) . . . . ? C6 C7 C9 C10 30.8(17) . . . . ? N3 C9 C10 C11 -166.7(9) . . . . ? C7 C9 C10 C11 13.5(15) . . . . ? N3 C9 C10 C14 8.9(13) . . . . ? C7 C9 C10 C14 -170.9(9) . . . . ? C15 N2 C14 C13 171.6(9) . . . . ? C15 N2 C14 C10 -4.8(14) . . . . ? C11 C10 C14 N2 173.0(8) . . . . ? C9 C10 C14 N2 -2.9(13) . . . . ? C11 C10 C14 C13 -3.5(13) . . . . ? C9 C10 C14 C13 -179.4(9) . . . . ? N2 C14 C13 C12 -176.1(9) . . . . ? C10 C14 C13 C12 0.4(13) . . . . ? N2 C14 C13 C21 4.8(18) . . . . ? C10 C14 C13 C21 -178.7(11) . . . . ? C12 C13 C21 C16 -1.4(11) . . . . ? C14 C13 C21 C16 177.8(11) . . . . ? C12 C13 C21 C20 179.4(10) . . . . ? C14 C13 C21 C20 -1(2) . . . . ? C20 C21 C16 C17 1.0(15) . . . . ? C13 C21 C16 C17 -178.3(9) . . . . ? C20 C21 C16 O2 -178.5(8) . . . . ? C13 C21 C16 O2 2.1(11) . . . . ? C12 O2 C16 C21 -1.9(10) . . . . ? C12 O2 C16 C17 178.5(9) . . . . ? C23 O1 C17 C18 132.9(9) . . . . ? C23 O1 C17 C16 -51.7(14) . . . . ? C21 C16 C17 O1 -177.0(9) . . . . ? O2 C16 C17 O1 2.5(16) . . . . ? C21 C16 C17 C18 -1.6(15) . . . . ? O2 C16 C17 C18 177.9(8) . . . . ? C11 N1 C12 C13 -3.3(15) . . . . ? C11 N1 C12 O2 179.3(8) . . . . ? C14 C13 C12 N1 3.3(15) . . . . ? C21 C13 C12 N1 -177.3(9) . . . . ? C14 C13 C12 O2 -179.2(8) . . . . ? C21 C13 C12 O2 0.2(11) . . . . ? C16 O2 C12 N1 178.9(8) . . . . ? C16 O2 C12 C13 1.0(10) . . . . ? C12 N1 C11 C10 -0.5(13) . . . . ? C9 C10 C11 N1 179.3(9) . . . . ? C14 C10 C11 N1 3.7(14) . . . . ? C14 N2 C15 N3 7.5(15) . . . . ? C9 N3 C15 N2 -1.6(16) . . . . ? C1 O3 C8 N4 -175.7(8) . . . . ? C1 O3 C8 C7 2.2(11) . . . . ? C9 C7 C8 N4 -2.6(18) . . . . ? C6 C7 C8 N4 174.6(11) . . . . ? C9 C7 C8 O3 -179.9(9) . . . . ? C6 C7 C8 O3 -2.7(11) . . . . ? C1 C6 C5 C4 1.7(14) . . . . ? C7 C6 C5 C4 176.8(11) . . . . ? C6 C5 C4 C3 0.1(15) . . . . ? C1 C2 C3 C4 1.3(14) . . . . ? O4 C2 C3 C4 -178.6(9) . . . . ? C5 C4 C3 C2 -1.7(15) . . . . ? C16 C21 C20 C19 0.4(13) . . . . ? C13 C21 C20 C19 179.5(10) . . . . ? C21 C20 C19 C18 -1.2(15) . . . . ? O1 C17 C18 C19 176.6(9) . . . . ? C16 C17 C18 C19 0.8(15) . . . . ? C20 C19 C18 C17 0.6(16) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.200 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 945368'