# 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 n.simpkins@bham.ac.uk _publ_contact_author_name 'Nigel Simpkins' loop_ _publ_author_name 'Nigel Simpkins' 'Ilias Pavlakos' 'Louise Male' data_Ip-683-2 _database_code_depnum_ccdc_archive 'CCDC 848586' #TrackingRef 'IP-683-2_Re-Label.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N3 O2' _chemical_formula_sum 'C21 H25 N3 O2' _chemical_formula_weight 351.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.25880(10) _cell_length_b 11.7630(2) _cell_length_c 12.8358(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1699.94(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8004 _cell_measurement_theta_min 3.444 _cell_measurement_theta_max 70.558 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8705 _exptl_absorpt_correction_T_max 0.9321 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 8778 reflections reduced R(int) from 0.0475 to 0.0277 Ratio of minimum to maximum apparent transmission: 0.817414 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10076 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.44 _diffrn_reflns_theta_max 66.57 _reflns_number_total 2910 _reflns_number_gt 2805 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0537P)^2^+0.3250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _chemical_absolute_configuration syn _refine_ls_number_reflns 2910 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C1 C 1.00067(16) 0.26334(15) 0.94610(15) 0.0260(4) Uani 1 1 d . . . H1A H 0.9512 0.2438 0.8849 0.031 Uiso 1 1 calc R . . H1B H 0.9730 0.2190 1.0070 0.031 Uiso 1 1 calc R . . C2 C 1.13239(16) 0.24177(16) 0.92425(16) 0.0301(4) Uani 1 1 d . . . H2A H 1.1510 0.2537 0.8497 0.036 Uiso 1 1 calc R . . H2B H 1.1552 0.1634 0.9440 0.036 Uiso 1 1 calc R . . C3 C 1.19606(15) 0.32939(16) 0.99249(16) 0.0282(4) Uani 1 1 d . . . H3A H 1.2047 0.3011 1.0647 0.034 Uiso 1 1 calc R . . H3B H 1.2758 0.3469 0.9643 0.034 Uiso 1 1 calc R . . C4 C 1.11675(15) 0.43377(15) 0.98926(13) 0.0232(4) Uani 1 1 d . . . C5 C 1.10807(15) 0.50657(16) 1.08850(14) 0.0248(4) Uani 1 1 d . . . H5A H 1.1847 0.5455 1.1012 0.030 Uiso 1 1 calc R . . H5B H 1.0907 0.4574 1.1492 0.030 Uiso 1 1 calc R . . C6 C 1.00766(15) 0.59600(15) 1.07524(12) 0.0204(3) Uani 1 1 d . . . H6 H 1.0473 0.6721 1.0755 0.025 Uiso 1 1 calc R . . C7 C 0.91529(15) 0.59824(15) 1.16476(12) 0.0210(4) Uani 1 1 d . . . C8 C 0.82663(15) 0.69694(14) 1.14194(12) 0.0204(4) Uani 1 1 d . . . H8 H 0.8673 0.7710 1.1558 0.024 Uiso 1 1 calc R . . C10 C 0.63155(15) 0.63318(15) 1.14901(13) 0.0216(4) Uani 1 1 d . . . C11 C 0.52722(15) 0.58346(15) 1.18472(13) 0.0233(4) Uani 1 1 d . . . H11 H 0.5082 0.5837 1.2568 0.028 Uiso 1 1 calc R . . C12 C 0.45151(15) 0.53346(15) 1.11283(14) 0.0243(4) Uani 1 1 d . . . H12 H 0.3812 0.4970 1.1364 0.029 Uiso 1 1 calc R . . C13 C 0.47696(15) 0.53596(14) 1.00703(14) 0.0245(4) Uani 1 1 d . . . H13 H 0.4230 0.5033 0.9586 0.029 Uiso 1 1 calc R . . C14 C 0.58165(15) 0.58639(14) 0.97182(13) 0.0222(4) Uani 1 1 d . . . H14 H 0.5993 0.5882 0.8995 0.027 Uiso 1 1 calc R . . C15 C 0.65936(15) 0.63360(14) 1.04278(13) 0.0202(3) Uani 1 1 d . . . C16 C 0.77386(16) 0.69960(14) 1.02987(13) 0.0199(3) Uani 1 1 d . . . H16 H 0.7491 0.7802 1.0180 0.024 Uiso 1 1 calc R . . C17 C 0.86030(15) 0.67169(14) 0.94091(12) 0.0200(3) Uani 1 1 d . . . H17A H 0.8134 0.6465 0.8799 0.024 Uiso 1 1 calc R . . H17B H 0.9021 0.7424 0.9209 0.024 Uiso 1 1 calc R . . C18 C 0.95282(14) 0.58113(14) 0.96482(12) 0.0186(3) Uani 1 1 d . . . C19 C 0.90849(14) 0.45801(14) 0.94775(12) 0.0174(3) Uani 1 1 d . . . C22 C 1.14393(14) 0.51598(14) 0.89893(12) 0.0209(3) Uani 1 1 d . . . C23 C 0.98091(17) 0.62810(17) 1.26622(13) 0.0274(4) Uani 1 1 d . . . H23A H 1.0383 0.5680 1.2826 0.041 Uiso 1 1 calc R . . H23B H 0.9234 0.6348 1.3232 0.041 Uiso 1 1 calc R . . H23C H 1.0228 0.7005 1.2575 0.041 Uiso 1 1 calc R . . C24 C 0.85206(15) 0.48341(15) 1.17906(12) 0.0223(4) Uani 1 1 d . . . H24A H 0.9113 0.4237 1.1907 0.033 Uiso 1 1 calc R . . H24B H 0.8060 0.4658 1.1164 0.033 Uiso 1 1 calc R . . H24C H 0.7987 0.4876 1.2392 0.033 Uiso 1 1 calc R . . N9 N 0.71798(13) 0.69085(13) 1.20659(11) 0.0233(3) Uani 1 1 d . . . H9 H 0.7094 0.7185 1.2698 0.028 Uiso 1 1 calc R . . N20 N 0.99745(12) 0.38532(12) 0.96736(11) 0.0214(3) Uani 1 1 d . . . N21 N 1.05357(12) 0.59126(12) 0.89038(10) 0.0202(3) Uani 1 1 d . . . H21 H 1.0544 0.6446 0.8423 0.024 Uiso 1 1 calc R . . O19 O 0.80886(10) 0.43123(10) 0.91692(9) 0.0207(3) Uani 1 1 d . . . O22 O 1.23369(10) 0.51410(11) 0.84528(10) 0.0273(3) 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 C1 0.0245(9) 0.0195(8) 0.0339(9) 0.0022(7) 0.0005(8) 0.0019(7) C2 0.0247(9) 0.0235(9) 0.0421(10) -0.0002(8) 0.0018(9) 0.0063(8) C3 0.0192(8) 0.0267(9) 0.0387(10) 0.0051(8) -0.0012(8) 0.0052(7) C4 0.0160(8) 0.0252(9) 0.0283(9) 0.0028(7) -0.0020(7) 0.0001(7) C5 0.0197(8) 0.0295(9) 0.0251(8) 0.0018(7) -0.0042(7) -0.0026(7) C6 0.0191(8) 0.0215(8) 0.0207(8) 0.0011(6) -0.0028(7) -0.0035(7) C7 0.0220(8) 0.0236(9) 0.0174(7) 0.0003(7) -0.0024(7) -0.0037(7) C8 0.0228(8) 0.0200(8) 0.0184(8) 0.0001(6) -0.0001(7) -0.0036(7) C10 0.0207(8) 0.0204(8) 0.0238(8) 0.0010(6) -0.0013(7) 0.0043(7) C11 0.0226(8) 0.0250(8) 0.0223(8) 0.0052(7) 0.0021(7) 0.0029(7) C12 0.0182(8) 0.0223(8) 0.0324(9) 0.0032(7) 0.0003(7) 0.0016(7) C13 0.0210(9) 0.0206(8) 0.0317(9) -0.0026(7) -0.0044(7) 0.0023(7) C14 0.0223(8) 0.0214(8) 0.0229(8) -0.0010(7) -0.0016(7) 0.0054(7) C15 0.0207(8) 0.0172(7) 0.0228(8) 0.0010(6) -0.0003(7) 0.0033(7) C16 0.0222(8) 0.0170(8) 0.0206(8) 0.0020(6) -0.0012(7) 0.0012(7) C17 0.0212(8) 0.0202(8) 0.0186(8) 0.0021(6) -0.0010(7) -0.0014(7) C18 0.0176(7) 0.0192(8) 0.0191(7) 0.0017(6) 0.0013(6) -0.0015(7) C19 0.0175(8) 0.0199(8) 0.0147(7) 0.0009(6) 0.0013(6) 0.0010(6) C22 0.0176(8) 0.0218(8) 0.0233(8) -0.0037(7) -0.0014(7) -0.0023(7) C23 0.0283(9) 0.0318(10) 0.0220(8) -0.0007(7) -0.0033(7) -0.0016(8) C24 0.0227(8) 0.0241(9) 0.0201(8) 0.0039(7) -0.0010(6) -0.0012(7) N9 0.0249(7) 0.0255(7) 0.0194(7) -0.0045(6) 0.0015(6) -0.0015(6) N20 0.0171(7) 0.0199(7) 0.0272(7) 0.0013(6) -0.0006(6) -0.0008(6) N21 0.0199(7) 0.0200(7) 0.0207(7) 0.0026(5) 0.0012(6) -0.0019(6) O19 0.0181(6) 0.0228(6) 0.0211(5) -0.0011(5) -0.0020(5) -0.0016(5) O22 0.0208(6) 0.0307(7) 0.0305(6) -0.0006(5) 0.0034(5) 0.0011(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N20 1.461(2) . ? C1 C2 1.530(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.531(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N20 1.486(2) . ? C4 C5 1.538(3) . ? C4 C22 1.541(2) . ? C5 C6 1.554(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.550(2) . ? C6 C18 1.556(2) . ? C6 H6 1.0000 . ? C7 C24 1.538(2) . ? C7 C23 1.538(2) . ? C7 C8 1.559(2) . ? C8 N9 1.480(2) . ? C8 C16 1.557(2) . ? C8 H8 1.0000 . ? C10 C11 1.390(2) . ? C10 N9 1.398(2) . ? C10 C15 1.399(2) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.395(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.514(2) . ? C16 C17 1.536(2) . ? C16 H16 1.0000 . ? C17 C18 1.521(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N21 1.488(2) . ? C18 C19 1.547(2) . ? C19 O19 1.230(2) . ? C19 N20 1.341(2) . ? C22 O22 1.223(2) . ? C22 N21 1.353(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N9 H9 0.8800 . ? N21 H21 0.8800 . ? 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 N20 C1 C2 102.77(14) . . ? N20 C1 H1A 111.2 . . ? C2 C1 H1A 111.2 . . ? N20 C1 H1B 111.2 . . ? C2 C1 H1B 111.2 . . ? H1A C1 H1B 109.1 . . ? C1 C2 C3 103.73(15) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C4 C3 C2 104.68(14) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? N20 C4 C3 103.10(14) . . ? N20 C4 C5 108.23(14) . . ? C3 C4 C5 117.70(15) . . ? N20 C4 C22 106.14(13) . . ? C3 C4 C22 114.28(14) . . ? C5 C4 C22 106.64(13) . . ? C4 C5 C6 109.42(13) . . ? C4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C5 114.74(13) . . ? C7 C6 C18 114.27(13) . . ? C5 C6 C18 108.21(13) . . ? C7 C6 H6 106.3 . . ? C5 C6 H6 106.3 . . ? C18 C6 H6 106.3 . . ? C24 C7 C23 108.78(14) . . ? C24 C7 C6 112.59(14) . . ? C23 C7 C6 108.02(13) . . ? C24 C7 C8 112.35(13) . . ? C23 C7 C8 107.26(14) . . ? C6 C7 C8 107.64(13) . . ? N9 C8 C16 101.76(13) . . ? N9 C8 C7 112.82(13) . . ? C16 C8 C7 115.66(13) . . ? N9 C8 H8 108.8 . . ? C16 C8 H8 108.8 . . ? C7 C8 H8 108.8 . . ? C11 C10 N9 128.19(15) . . ? C11 C10 C15 120.79(16) . . ? N9 C10 C15 110.97(15) . . ? C12 C11 C10 118.58(15) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 121.00(16) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 120.03(16) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.54(16) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C10 120.01(16) . . ? C14 C15 C16 132.39(15) . . ? C10 C15 C16 107.40(14) . . ? C15 C16 C17 120.75(14) . . ? C15 C16 C8 102.33(13) . . ? C17 C16 C8 116.16(13) . . ? C15 C16 H16 105.4 . . ? C17 C16 H16 105.4 . . ? C8 C16 H16 105.4 . . ? C18 C17 C16 115.69(13) . . ? C18 C17 H17A 108.4 . . ? C16 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? C16 C17 H17B 108.4 . . ? H17A C17 H17B 107.4 . . ? N21 C18 C17 109.65(13) . . ? N21 C18 C19 103.29(12) . . ? C17 C18 C19 113.95(13) . . ? N21 C18 C6 105.87(13) . . ? C17 C18 C6 112.14(14) . . ? C19 C18 C6 111.24(12) . . ? O19 C19 N20 125.32(15) . . ? O19 C19 C18 125.39(15) . . ? N20 C19 C18 109.23(14) . . ? O22 C22 N21 125.97(16) . . ? O22 C22 C4 125.20(15) . . ? N21 C22 C4 108.81(13) . . ? C7 C23 H23A 109.5 . . ? C7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7 C24 H24A 109.5 . . ? C7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 N9 C8 107.60(13) . . ? C10 N9 H9 126.2 . . ? C8 N9 H9 126.2 . . ? C19 N20 C1 127.57(15) . . ? C19 N20 C4 117.79(14) . . ? C1 N20 C4 112.93(14) . . ? C22 N21 C18 117.95(13) . . ? C22 N21 H21 121.0 . . ? C18 N21 H21 121.0 . . ? 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 N20 C1 C2 C3 31.37(19) . . . . ? C1 C2 C3 C4 -36.1(2) . . . . ? C2 C3 C4 N20 25.96(18) . . . . ? C2 C3 C4 C5 144.96(16) . . . . ? C2 C3 C4 C22 -88.75(18) . . . . ? N20 C4 C5 C6 -54.29(17) . . . . ? C3 C4 C5 C6 -170.54(15) . . . . ? C22 C4 C5 C6 59.53(16) . . . . ? C4 C5 C6 C7 127.97(15) . . . . ? C4 C5 C6 C18 -0.93(17) . . . . ? C5 C6 C7 C24 -59.01(18) . . . . ? C18 C6 C7 C24 66.80(18) . . . . ? C5 C6 C7 C23 61.11(18) . . . . ? C18 C6 C7 C23 -173.07(14) . . . . ? C5 C6 C7 C8 176.63(13) . . . . ? C18 C6 C7 C8 -57.55(17) . . . . ? C24 C7 C8 N9 41.40(18) . . . . ? C23 C7 C8 N9 -78.08(17) . . . . ? C6 C7 C8 N9 165.90(13) . . . . ? C24 C7 C8 C16 -75.17(18) . . . . ? C23 C7 C8 C16 165.34(14) . . . . ? C6 C7 C8 C16 49.33(18) . . . . ? N9 C10 C11 C12 177.82(17) . . . . ? C15 C10 C11 C12 0.5(2) . . . . ? C10 C11 C12 C13 -2.1(3) . . . . ? C11 C12 C13 C14 1.9(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C10 -1.6(3) . . . . ? C13 C14 C15 C16 -175.62(16) . . . . ? C11 C10 C15 C14 1.4(3) . . . . ? N9 C10 C15 C14 -176.42(15) . . . . ? C11 C10 C15 C16 176.76(15) . . . . ? N9 C10 C15 C16 -1.02(19) . . . . ? C14 C15 C16 C17 -35.0(3) . . . . ? C10 C15 C16 C17 150.36(15) . . . . ? C14 C15 C16 C8 -165.97(18) . . . . ? C10 C15 C16 C8 19.42(17) . . . . ? N9 C8 C16 C15 -29.37(15) . . . . ? C7 C8 C16 C15 93.27(16) . . . . ? N9 C8 C16 C17 -163.04(14) . . . . ? C7 C8 C16 C17 -40.4(2) . . . . ? C15 C16 C17 C18 -88.54(19) . . . . ? C8 C16 C17 C18 36.2(2) . . . . ? C16 C17 C18 N21 -160.03(13) . . . . ? C16 C17 C18 C19 84.77(17) . . . . ? C16 C17 C18 C6 -42.72(19) . . . . ? C7 C6 C18 N21 175.19(13) . . . . ? C5 C6 C18 N21 -55.65(15) . . . . ? C7 C6 C18 C17 55.64(18) . . . . ? C5 C6 C18 C17 -175.20(13) . . . . ? C7 C6 C18 C19 -73.29(17) . . . . ? C5 C6 C18 C19 55.88(17) . . . . ? N21 C18 C19 O19 -118.27(17) . . . . ? C17 C18 C19 O19 0.6(2) . . . . ? C6 C18 C19 O19 128.57(16) . . . . ? N21 C18 C19 N20 58.98(15) . . . . ? C17 C18 C19 N20 177.87(14) . . . . ? C6 C18 C19 N20 -54.18(17) . . . . ? N20 C4 C22 O22 -127.07(17) . . . . ? C3 C4 C22 O22 -14.2(2) . . . . ? C5 C4 C22 O22 117.69(18) . . . . ? N20 C4 C22 N21 54.06(16) . . . . ? C3 C4 C22 N21 166.97(14) . . . . ? C5 C4 C22 N21 -61.17(16) . . . . ? C11 C10 N9 C8 163.11(16) . . . . ? C15 C10 N9 C8 -19.32(19) . . . . ? C16 C8 N9 C10 30.23(17) . . . . ? C7 C8 N9 C10 -94.34(16) . . . . ? O19 C19 N20 C1 7.4(3) . . . . ? C18 C19 N20 C1 -169.90(15) . . . . ? O19 C19 N20 C4 171.30(15) . . . . ? C18 C19 N20 C4 -5.96(19) . . . . ? C2 C1 N20 C19 148.68(17) . . . . ? C2 C1 N20 C4 -15.91(19) . . . . ? C3 C4 N20 C19 -172.49(14) . . . . ? C5 C4 N20 C19 62.12(18) . . . . ? C22 C4 N20 C19 -52.03(18) . . . . ? C3 C4 N20 C1 -6.25(19) . . . . ? C5 C4 N20 C1 -131.64(15) . . . . ? C22 C4 N20 C1 114.20(15) . . . . ? O22 C22 N21 C18 -178.62(16) . . . . ? C4 C22 N21 C18 0.23(19) . . . . ? C17 C18 N21 C22 -178.99(13) . . . . ? C19 C18 N21 C22 -57.17(17) . . . . ? C6 C18 N21 C22 59.84(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9 O19 0.88 2.59 3.0728(19) 115.4 2_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 66.57 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.362 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.042