# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zhaolchem@mail.tsinghua.edu.cn _publ_contact_author_name 'Liang Zhao' loop_ _publ_author_name 'Mei-Xiang Wang' 'Li-Xia Wang' 'Liang Zhao' 'De-Xian Wang' data_Py3Pm3 _database_code_depnum_ccdc_archive 'CCDC 813213' #TrackingRef 'Py3Pm3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 N15' _chemical_formula_weight 639.74 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.180(2) _cell_length_b 15.180(2) _cell_length_c 27.583(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5504.3(15) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.9704 _exptl_absorpt_correction_T_max 0.9704 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5464 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.41 _reflns_number_total 2800 _reflns_number_gt 1926 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0901P)^2^+15.1661P] 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 2800 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.2049 _refine_ls_wR_factor_gt 0.1914 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 N1 N 0.86338(18) 0.79954(17) 0.06454(8) 0.0283(5) Uani 1 1 d . . . N2 N 0.54629(17) 0.51700(17) 0.07985(8) 0.0261(5) Uani 1 1 d . . . N3 N 1.00437(18) 0.77074(17) 0.05662(8) 0.0278(5) Uani 1 1 d . . . N4 N 0.70121(18) 0.66785(16) 0.08397(9) 0.0296(6) Uani 1 1 d . . . N5 N 0.99087(18) 0.61460(19) 0.07154(9) 0.0327(6) Uani 1 1 d . . . C8 C 0.6340(2) 0.5712(2) 0.10416(10) 0.0265(6) Uani 1 1 d . . . C9 C 0.9435(2) 0.6728(2) 0.06970(9) 0.0263(6) Uani 1 1 d . . . C10 C 0.9594(2) 0.8268(2) 0.05486(10) 0.0284(6) Uani 1 1 d . . . H10A H 1.0018 0.8956 0.0454 0.034 Uiso 1 1 calc R . . C11 C 0.4913(2) 0.3887(2) 0.14123(10) 0.0323(7) Uani 1 1 d . . . H11A H 0.4398 0.3255 0.1538 0.039 Uiso 1 1 calc R . . C12 C 0.6559(2) 0.5379(2) 0.14663(10) 0.0306(6) Uani 1 1 d . . . H12A H 0.7193 0.5775 0.1626 0.037 Uiso 1 1 calc R . . C13 C 0.8408(2) 0.6329(2) 0.07827(10) 0.0279(6) Uani 1 1 d . . . H13A H 0.7977 0.5628 0.0854 0.033 Uiso 1 1 calc R . . C14 C 0.8030(2) 0.7001(2) 0.07606(9) 0.0241(6) Uani 1 1 d . . . C15 C 0.5823(2) 0.4448(2) 0.16539(10) 0.0325(7) Uani 1 1 d . . . H15A H 0.5946 0.4201 0.1947 0.039 Uiso 1 1 calc R . . C16 C 0.4769(2) 0.4270(2) 0.09771(10) 0.0261(6) Uani 1 1 d . . . C17 C 0.6580(2) 0.7289(2) 0.06659(11) 0.0335(7) Uani 1 1 d . . . H17A H 0.7125 0.7937 0.0539 0.050 Uiso 1 1 calc R . . H17B H 0.6237 0.7420 0.0934 0.050 Uiso 1 1 calc R . . H17C H 0.6088 0.6921 0.0408 0.050 Uiso 1 1 calc R . . C18 C 1.0839(2) 0.6455(2) 0.04411(12) 0.0382(7) Uani 1 1 d . . . H18A H 1.1067 0.5962 0.0493 0.057 Uiso 1 1 calc R . . H18B H 1.1368 0.7129 0.0550 0.057 Uiso 1 1 calc R . . H18C H 1.0706 0.6482 0.0095 0.057 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 N1 0.0322(13) 0.0196(11) 0.0269(12) 0.0005(9) -0.0025(9) 0.0082(10) N2 0.0205(11) 0.0254(12) 0.0292(12) -0.0024(9) -0.0010(9) 0.0090(10) N3 0.0300(13) 0.0203(12) 0.0287(12) 0.0006(9) -0.0035(9) 0.0092(10) N4 0.0276(13) 0.0182(11) 0.0416(14) 0.0008(9) 0.0006(10) 0.0104(10) N5 0.0321(14) 0.0254(13) 0.0405(15) 0.0046(10) 0.0058(10) 0.0143(11) C8 0.0308(15) 0.0235(14) 0.0275(14) -0.0035(10) -0.0015(11) 0.0152(12) C9 0.0296(14) 0.0285(15) 0.0197(13) -0.0036(10) -0.0045(10) 0.0137(12) C10 0.0283(15) 0.0212(13) 0.0280(14) 0.0026(10) -0.0026(11) 0.0066(12) C11 0.0310(15) 0.0263(15) 0.0296(15) 0.0032(11) 0.0056(12) 0.0069(12) C12 0.0305(15) 0.0258(15) 0.0300(15) -0.0026(11) -0.0021(11) 0.0101(12) C13 0.0292(15) 0.0190(13) 0.0309(14) -0.0029(10) -0.0051(11) 0.0086(12) C14 0.0305(14) 0.0212(13) 0.0185(12) -0.0029(9) -0.0063(10) 0.0114(11) C15 0.0388(17) 0.0324(16) 0.0205(13) 0.0015(11) 0.0016(11) 0.0135(13) C16 0.0248(14) 0.0253(14) 0.0277(14) -0.0011(11) 0.0011(11) 0.0122(12) C17 0.0331(16) 0.0265(15) 0.0402(17) 0.0055(12) -0.0017(12) 0.0144(13) C18 0.0363(17) 0.0311(16) 0.0483(18) 0.0036(13) 0.0110(14) 0.0176(14) _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 N1 C10 1.329(4) . ? N1 C14 1.355(3) . ? N2 C16 1.334(3) . ? N2 C8 1.343(3) . ? N3 C10 1.331(4) . ? N3 C9 1.349(3) . ? N4 C14 1.385(4) . ? N4 C8 1.417(3) . ? N4 C17 1.458(4) . ? N5 C9 1.391(4) . ? N5 C16 1.405(4) 3_665 ? N5 C18 1.457(4) . ? C8 C12 1.380(4) . ? C9 C13 1.381(4) . ? C10 H10A 0.9500 . ? C11 C15 1.378(4) . ? C11 C16 1.398(4) . ? C11 H11A 0.9500 . ? C12 C15 1.391(4) . ? C12 H12A 0.9500 . ? C13 C14 1.401(4) . ? C13 H13A 0.9500 . ? C15 H15A 0.9500 . ? C16 N5 1.405(4) 2_655 ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C10 N1 C14 114.8(2) . . ? C16 N2 C8 118.4(2) . . ? C10 N3 C9 115.2(2) . . ? C14 N4 C8 121.7(2) . . ? C14 N4 C17 120.0(2) . . ? C8 N4 C17 117.9(2) . . ? C9 N5 C16 122.3(2) . 3_665 ? C9 N5 C18 120.1(2) . . ? C16 N5 C18 117.5(2) 3_665 . ? N2 C8 C12 123.1(3) . . ? N2 C8 N4 114.7(2) . . ? C12 C8 N4 122.2(3) . . ? N3 C9 C13 122.0(3) . . ? N3 C9 N5 115.0(2) . . ? C13 C9 N5 122.9(3) . . ? N1 C10 N3 128.8(3) . . ? N1 C10 H10A 115.6 . . ? N3 C10 H10A 115.6 . . ? C15 C11 C16 118.3(3) . . ? C15 C11 H11A 120.8 . . ? C16 C11 H11A 120.8 . . ? C8 C12 C15 118.0(3) . . ? C8 C12 H12A 121.0 . . ? C15 C12 H12A 121.0 . . ? C9 C13 C14 117.2(3) . . ? C9 C13 H13A 121.4 . . ? C14 C13 H13A 121.4 . . ? N1 C14 N4 116.4(2) . . ? N1 C14 C13 121.7(3) . . ? N4 C14 C13 121.8(2) . . ? C11 C15 C12 119.7(3) . . ? C11 C15 H15A 120.1 . . ? C12 C15 H15A 120.1 . . ? N2 C16 C11 122.4(3) . . ? N2 C16 N5 115.5(2) . 2_655 ? C11 C16 N5 122.0(2) . 2_655 ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C16 N2 C8 C12 0.2(4) . . . . ? C16 N2 C8 N4 -177.0(2) . . . . ? C14 N4 C8 N2 -131.1(3) . . . . ? C17 N4 C8 N2 42.3(3) . . . . ? C14 N4 C8 C12 51.7(4) . . . . ? C17 N4 C8 C12 -135.0(3) . . . . ? C10 N3 C9 C13 3.0(4) . . . . ? C10 N3 C9 N5 -179.9(2) . . . . ? C16 N5 C9 N3 160.3(2) 3_665 . . . ? C18 N5 C9 N3 -22.3(4) . . . . ? C16 N5 C9 C13 -22.7(4) 3_665 . . . ? C18 N5 C9 C13 154.7(3) . . . . ? C14 N1 C10 N3 -2.6(4) . . . . ? C9 N3 C10 N1 0.5(4) . . . . ? N2 C8 C12 C15 -1.3(4) . . . . ? N4 C8 C12 C15 175.7(3) . . . . ? N3 C9 C13 C14 -4.2(4) . . . . ? N5 C9 C13 C14 179.0(2) . . . . ? C10 N1 C14 N4 -176.8(2) . . . . ? C10 N1 C14 C13 1.1(4) . . . . ? C8 N4 C14 N1 -169.1(2) . . . . ? C17 N4 C14 N1 17.7(4) . . . . ? C8 N4 C14 C13 13.0(4) . . . . ? C17 N4 C14 C13 -160.2(3) . . . . ? C9 C13 C14 N1 2.0(4) . . . . ? C9 C13 C14 N4 179.9(2) . . . . ? C16 C11 C15 C12 1.1(4) . . . . ? C8 C12 C15 C11 0.6(4) . . . . ? C8 N2 C16 C11 1.6(4) . . . . ? C8 N2 C16 N5 177.6(2) . . . 2_655 ? C15 C11 C16 N2 -2.3(4) . . . . ? C15 C11 C16 N5 -178.0(3) . . . 2_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.417 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.061 # Attachment 'Py3Pm3C60.cif' data_Py3Pm3C60 _database_code_depnum_ccdc_archive 'CCDC 813214' #TrackingRef 'Py3Pm3C60.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C126 H66 N30' _chemical_formula_weight 2000.09 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 15.117(2) _cell_length_b 15.117(2) _cell_length_c 88.648(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 17545(5) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16561 _cell_measurement_theta_min 1.3783 _cell_measurement_theta_max 27.4791 _exptl_crystal_description Prism _exptl_crystal_colour Purple _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6192 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44950 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -114 _diffrn_reflns_limit_l_max 114 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4471 _reflns_number_gt 4462 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4471 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1808 _refine_ls_R_factor_gt 0.1791 _refine_ls_wR_factor_ref 0.5190 _refine_ls_wR_factor_gt 0.5182 _refine_ls_goodness_of_fit_ref 2.605 _refine_ls_restrained_S_all 2.605 _refine_ls_shift/su_max 1.971 _refine_ls_shift/su_mean 0.177 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 N1 N 1.3395(3) 1.0529(3) 0.05616(4) 0.0305(9) Uani 1 1 d . . . N2 N 1.2042(3) 0.7406(3) 0.05004(4) 0.0326(9) Uani 1 1 d . . . N3 N 1.3500(3) 0.9101(3) 0.04977(4) 0.0327(9) Uani 1 1 d . . . N4 N 1.0431(3) 0.7112(2) 0.05619(4) 0.0281(8) Uani 1 1 d . . . N5 N 0.8808(2) 0.6929(2) 0.05692(4) 0.0255(8) Uani 1 1 d . . . C1 C 0.8629(5) 1.0924(5) 0.02107(6) 0.0531(16) Uani 1 1 d . . . C2 C 0.8406(4) 1.1047(4) 0.00656(6) 0.0484(13) Uani 1 1 d . . . C3 C 0.7756(3) 1.0176(4) -0.00216(6) 0.0443(12) Uani 1 1 d . . . C4 C 0.7364(3) 0.9186(4) 0.00175(7) 0.0477(13) Uani 1 1 d . . . C5 C 0.7596(4) 0.9020(5) 0.01818(6) 0.0502(14) Uani 1 1 d . . . C6 C 0.7732(4) 0.8185(5) 0.01834(6) 0.0542(16) Uani 1 1 d . . . C7 C 0.8450(4) 0.8153(3) 0.02699(4) 0.0326(10) Uani 1 1 d . . . C8 C 0.9127(3) 0.9007(3) 0.03667(4) 0.0309(10) Uani 1 1 d . . . C9 C 0.8999(3) 0.9856(3) 0.03663(4) 0.0294(9) Uani 1 1 d . . . C10 C 0.8206(4) 0.9832(4) 0.02713(4) 0.0400(12) Uani 1 1 d . . . C11 C 1.4329(4) 1.1163(4) 0.04734(7) 0.0465(13) Uani 1 1 d . . . H11A H 1.4851 1.0989 0.0501 0.070 Uiso 1 1 calc R . . H11B H 1.4582 1.1886 0.0495 0.070 Uiso 1 1 calc R . . H11C H 1.4174 1.1037 0.0366 0.070 Uiso 1 1 calc R . . C12 C 1.2912(3) 0.9480(3) 0.05487(4) 0.0253(9) Uani 1 1 d . . . C13 C 1.1867(3) 0.8844(3) 0.05752(4) 0.0256(9) Uani 1 1 d . . . H13A H 1.1456 0.9111 0.0611 0.031 Uiso 1 1 calc R . . C14 C 1.1452(3) 0.7807(3) 0.05472(4) 0.0248(9) Uani 1 1 d . . . C15 C 1.3022(3) 0.8100(3) 0.04773(5) 0.0344(10) Uani 1 1 d . . . H15A H 1.3436 0.7837 0.0441 0.041 Uiso 1 1 calc R . . C16 C 0.9989(4) 0.6131(4) 0.04789(7) 0.0460(13) Uani 1 1 d . . . H16A H 1.0404 0.5810 0.0497 0.069 Uiso 1 1 calc R . . H16B H 0.9981 0.6258 0.0371 0.069 Uiso 1 1 calc R . . H16C H 0.9290 0.5676 0.0514 0.069 Uiso 1 1 calc R . . C17 C 0.9733(3) 0.7342(3) 0.06342(4) 0.0244(8) Uani 1 1 d . . . C18 C 0.9980(3) 0.7919(3) 0.07663(4) 0.0283(9) Uani 1 1 d . . . H18A H 1.0647 0.8221 0.0808 0.034 Uiso 1 1 calc R . . C19 C 0.9216(3) 0.8034(4) 0.08340(4) 0.0315(10) Uani 1 1 d . . . H19A H 0.9355 0.8412 0.0925 0.038 Uiso 1 1 calc R . . C20 C 0.8263(3) 0.7608(3) 0.07709(4) 0.0309(9) Uani 1 1 d . . . H20A H 0.7735 0.7676 0.0818 0.037 Uiso 1 1 calc R . . C21 C 0.8087(3) 0.7071(3) 0.06357(4) 0.0261(9) Uani 1 1 d . . . Q1 C 0.8344(8) 0.4735(8) 0.01491(12) 0.100(3) Uiso 1 1 d . . . Q2 C 1.2684(8) 0.7573(8) 0.01048(12) 0.096(3) Uiso 1 1 d . . . Q3 C 1.1537(10) 0.6320(10) 0.01529(14) 0.120(4) Uiso 1 1 d . . . Q4 C 0.803(2) 0.470(2) 0.0833 0.182(9) Uiso 1 2 d S . . Q5 C 1.6093(14) 1.3333 0.0833 0.129(6) Uiso 1 2 d S . . 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 N1 0.0232(16) 0.0303(17) 0.0397(19) 0.0007(14) 0.0025(13) 0.0146(13) N2 0.0353(19) 0.0331(18) 0.040(2) -0.0036(14) -0.0006(14) 0.0247(15) N3 0.0296(17) 0.0342(19) 0.043(2) 0.0038(15) 0.0033(14) 0.0224(15) N4 0.0265(17) 0.0235(16) 0.0363(18) -0.0011(13) -0.0012(13) 0.0141(13) N5 0.0257(16) 0.0244(15) 0.0286(17) 0.0023(12) 0.0005(12) 0.0142(13) C1 0.067(4) 0.091(4) 0.035(2) -0.008(3) 0.005(2) 0.065(4) C2 0.052(3) 0.061(3) 0.047(3) -0.004(2) 0.000(2) 0.039(3) C3 0.028(2) 0.042(3) 0.067(3) -0.006(2) -0.003(2) 0.0211(19) C4 0.0181(19) 0.048(3) 0.072(4) 0.010(2) 0.004(2) 0.0128(18) C5 0.035(2) 0.058(3) 0.047(3) 0.000(2) 0.016(2) 0.014(2) C6 0.028(2) 0.069(4) 0.041(3) 0.022(2) 0.0046(19) 0.006(2) C7 0.044(2) 0.032(2) 0.0158(17) 0.0056(14) 0.0083(15) 0.0145(18) C8 0.035(2) 0.032(2) 0.0210(18) 0.0078(14) 0.0069(14) 0.0126(17) C9 0.032(2) 0.035(2) 0.0201(18) -0.0006(14) 0.0037(14) 0.0154(17) C10 0.038(2) 0.072(3) 0.0185(19) -0.0011(19) 0.0051(16) 0.034(2) C11 0.030(2) 0.035(2) 0.075(4) 0.000(2) 0.016(2) 0.0167(19) C12 0.0275(18) 0.033(2) 0.0227(17) 0.0037(14) -0.0003(13) 0.0203(16) C13 0.0322(19) 0.0260(18) 0.0255(19) 0.0012(13) -0.0013(14) 0.0196(16) C14 0.0283(18) 0.0301(19) 0.0226(17) 0.0005(14) -0.0032(13) 0.0195(15) C15 0.031(2) 0.038(2) 0.046(2) -0.0021(18) 0.0033(17) 0.0253(18) C16 0.038(2) 0.033(2) 0.068(3) -0.019(2) -0.011(2) 0.019(2) C17 0.0252(17) 0.0239(17) 0.0241(17) 0.0068(13) 0.0031(13) 0.0123(14) C18 0.0237(17) 0.037(2) 0.0263(18) 0.0042(15) -0.0019(14) 0.0164(16) C19 0.033(2) 0.043(2) 0.0203(17) 0.0034(16) 0.0011(14) 0.0201(18) C20 0.0279(19) 0.044(2) 0.0264(18) 0.0026(16) 0.0042(15) 0.0221(18) C21 0.0220(17) 0.0266(18) 0.0286(19) 0.0069(14) 0.0012(14) 0.0115(14) _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 N1 C12 1.380(5) . ? N1 C21 1.409(5) 2_765 ? N1 C11 1.473(6) . ? N2 C15 1.335(6) . ? N2 C14 1.370(5) . ? N3 C15 1.323(6) . ? N3 C12 1.355(5) . ? N4 C14 1.372(5) . ? N4 C17 1.419(5) . ? N4 C16 1.482(5) . ? N5 C21 1.347(5) . ? N5 C17 1.343(5) . ? C1 C2 1.366(8) . ? C1 C7 1.506(8) 3_675 ? C1 C10 1.539(9) . ? C2 C4 1.386(8) 20_565 ? C2 C3 1.416(8) . ? C3 C4 1.351(7) . ? C3 C6 1.543(8) 20_565 ? C4 C2 1.386(8) 21_655 ? C4 C5 1.548(8) . ? C5 C10 1.362(8) . ? C5 C6 1.377(10) . ? C6 C7 1.349(7) . ? C6 C3 1.543(8) 21_655 ? C7 C8 1.459(6) . ? C7 C1 1.506(8) 2_765 ? C8 C9 1.446(6) 2_765 ? C8 C9 1.392(6) . ? C9 C8 1.446(6) 3_675 ? C9 C10 1.449(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.398(5) . ? C13 C14 1.388(5) . ? C13 H13A 0.9500 . ? C15 H15A 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.395(5) . ? C18 C19 1.388(6) . ? C18 H18A 0.9500 . ? C19 C20 1.369(6) . ? C19 H19A 0.9500 . ? C20 C21 1.396(6) . ? C20 H20A 0.9500 . ? C21 N1 1.409(5) 3_675 ? Q2 Q3 1.869(18) . ? Q4 Q5 1.20(3) 3_675 ? Q5 Q4 1.20(3) 2_765 ? Q5 Q5 1.50(4) 3_785 ? Q5 Q5 1.50(4) 2_865 ? 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 C12 N1 C21 121.5(3) . 2_765 ? C12 N1 C11 119.2(3) . . ? C21 N1 C11 118.3(3) 2_765 . ? C15 N2 C14 114.2(3) . . ? C15 N3 C12 115.5(3) . . ? C14 N4 C17 123.1(3) . . ? C14 N4 C16 119.4(4) . . ? C17 N4 C16 116.8(3) . . ? C21 N5 C17 118.4(3) . . ? C2 C1 C7 120.3(6) . 3_675 ? C2 C1 C10 118.5(5) . . ? C7 C1 C10 106.9(4) 3_675 . ? C1 C2 C4 116.9(6) . 20_565 ? C1 C2 C3 119.4(6) . . ? C4 C2 C3 113.4(5) 20_565 . ? C4 C3 C2 127.3(6) . . ? C4 C3 C6 115.5(5) . 20_565 ? C2 C3 C6 104.7(5) . 20_565 ? C3 C4 C2 128.2(6) . 21_655 ? C3 C4 C5 114.3(5) . . ? C2 C4 C5 105.5(5) 21_655 . ? C10 C5 C6 118.4(6) . . ? C10 C5 C4 120.5(5) . . ? C6 C5 C4 107.9(5) . . ? C7 C6 C5 122.0(6) . . ? C7 C6 C3 117.8(5) . 21_655 ? C5 C6 C3 108.5(4) . 21_655 ? C6 C7 C8 121.6(5) . . ? C6 C7 C1 121.0(5) . 2_765 ? C8 C7 C1 106.4(4) . 2_765 ? C9 C8 C9 119.9(4) 2_765 . ? C9 C8 C7 110.4(4) 2_765 . ? C9 C8 C7 117.1(4) . . ? C8 C9 C8 120.1(4) 3_675 . ? C8 C9 C10 109.8(4) 3_675 . ? C8 C9 C10 118.2(4) . . ? C5 C10 C9 122.7(5) . . ? C5 C10 C1 119.6(4) . . ? C9 C10 C1 106.3(4) . . ? N1 C11 H11A 109.4 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 N1 115.6(3) . . ? N3 C12 C13 121.3(3) . . ? N1 C12 C13 123.0(3) . . ? C14 C13 C12 117.7(3) . . ? C14 C13 H13A 121.2 . . ? C12 C13 H13A 121.2 . . ? N2 C14 N4 114.9(3) . . ? N2 C14 C13 121.8(3) . . ? N4 C14 C13 123.3(3) . . ? N3 C15 N2 129.4(4) . . ? N3 C15 H15A 115.2 . . ? N2 C15 H15A 115.4 . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.6 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.4 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N5 C17 C18 122.8(3) . . ? N5 C17 N4 115.0(3) . . ? C18 C17 N4 122.1(3) . . ? C19 C18 C17 117.5(4) . . ? C19 C18 H18A 121.3 . . ? C17 C18 H18A 121.3 . . ? C20 C19 C18 120.7(4) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.6 . . ? C19 C20 C21 118.3(4) . . ? C19 C20 H20A 120.8 . . ? C21 C20 H20A 120.8 . . ? N5 C21 C20 122.2(3) . . ? N5 C21 N1 115.0(3) . 3_675 ? C20 C21 N1 122.8(3) . 3_675 ? Q4 Q5 Q5 150.077(9) 2_765 3_785 ? Q4 Q5 Q5 149.923(14) 2_765 2_865 ? Q5 Q5 Q5 60.000(3) 3_785 2_865 ? 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 C7 C1 C2 C4 -5.2(7) 3_675 . . 20_565 ? C10 C1 C2 C4 -139.6(5) . . . 20_565 ? C7 C1 C2 C3 137.7(5) 3_675 . . . ? C10 C1 C2 C3 3.3(7) . . . . ? C1 C2 C3 C4 -5.5(8) . . . . ? C4 C2 C3 C4 138.6(6) 20_565 . . . ? C1 C2 C3 C6 -144.9(5) . . . 20_565 ? C4 C2 C3 C6 -0.8(6) 20_565 . . 20_565 ? C2 C3 C4 C2 -131.2(7) . . . 21_655 ? C6 C3 C4 C2 4.5(7) 20_565 . . 21_655 ? C2 C3 C4 C5 5.7(7) . . . . ? C6 C3 C4 C5 141.4(4) 20_565 . . . ? C3 C4 C5 C10 -4.2(7) . . . . ? C2 C4 C5 C10 141.9(5) 21_655 . . . ? C3 C4 C5 C6 -144.8(5) . . . . ? C2 C4 C5 C6 1.4(5) 21_655 . . . ? C10 C5 C6 C7 -0.3(7) . . . . ? C4 C5 C6 C7 141.2(5) . . . . ? C10 C5 C6 C3 -142.4(4) . . . 21_655 ? C4 C5 C6 C3 -0.9(5) . . . 21_655 ? C5 C6 C7 C8 -0.2(7) . . . . ? C3 C6 C7 C8 138.6(4) 21_655 . . . ? C5 C6 C7 C1 -139.3(5) . . . 2_765 ? C3 C6 C7 C1 -0.5(7) 21_655 . . 2_765 ? C6 C7 C8 C9 -141.9(4) . . . 2_765 ? C1 C7 C8 C9 2.4(4) 2_765 . . 2_765 ? C6 C7 C8 C9 0.1(6) . . . . ? C1 C7 C8 C9 144.4(4) 2_765 . . . ? C9 C8 C9 C8 -0.5(7) 2_765 . . 3_675 ? C7 C8 C9 C8 -138.8(3) . . . 3_675 ? C9 C8 C9 C10 138.6(3) 2_765 . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C6 C5 C10 C9 0.8(7) . . . . ? C4 C5 C10 C9 -135.8(5) . . . . ? C6 C5 C10 C1 139.3(5) . . . . ? C4 C5 C10 C1 2.8(7) . . . . ? C8 C9 C10 C5 142.2(4) 3_675 . . . ? C8 C9 C10 C5 -0.8(6) . . . . ? C8 C9 C10 C1 -1.0(4) 3_675 . . . ? C8 C9 C10 C1 -144.0(4) . . . . ? C2 C1 C10 C5 -2.3(7) . . . . ? C7 C1 C10 C5 -142.1(4) 3_675 . . . ? C2 C1 C10 C9 142.2(5) . . . . ? C7 C1 C10 C9 2.4(4) 3_675 . . . ? C15 N3 C12 N1 -176.4(4) . . . . ? C15 N3 C12 C13 -0.9(6) . . . . ? C21 N1 C12 N3 -169.6(3) 2_765 . . . ? C11 N1 C12 N3 21.7(6) . . . . ? C21 N1 C12 C13 15.1(6) 2_765 . . . ? C11 N1 C12 C13 -153.7(4) . . . . ? N3 C12 C13 C14 -0.1(6) . . . . ? N1 C12 C13 C14 175.1(4) . . . . ? C15 N2 C14 N4 175.9(4) . . . . ? C15 N2 C14 C13 -3.3(6) . . . . ? C17 N4 C14 N2 168.3(3) . . . . ? C16 N4 C14 N2 -21.9(6) . . . . ? C17 N4 C14 C13 -12.5(6) . . . . ? C16 N4 C14 C13 157.3(4) . . . . ? C12 C13 C14 N2 2.3(6) . . . . ? C12 C13 C14 N4 -176.9(3) . . . . ? C12 N3 C15 N2 -0.3(7) . . . . ? C14 N2 C15 N3 2.4(7) . . . . ? C21 N5 C17 C18 -0.7(5) . . . . ? C21 N5 C17 N4 176.7(3) . . . . ? C14 N4 C17 N5 141.6(4) . . . . ? C16 N4 C17 N5 -28.4(5) . . . . ? C14 N4 C17 C18 -40.9(5) . . . . ? C16 N4 C17 C18 149.1(4) . . . . ? N5 C17 C18 C19 2.1(6) . . . . ? N4 C17 C18 C19 -175.2(4) . . . . ? C17 C18 C19 C20 -1.1(6) . . . . ? C18 C19 C20 C21 -1.1(6) . . . . ? C17 N5 C21 C20 -1.6(5) . . . . ? C17 N5 C21 N1 -179.3(3) . . . 3_675 ? C19 C20 C21 N5 2.5(6) . . . . ? C19 C20 C21 N1 180.0(4) . . . 3_675 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.924 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.272