# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 900999' #TrackingRef 'Compound 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H29 N O' _chemical_formula_weight 371.50 _chemical_absolute_configuration syn 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 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.984(5) _cell_length_b 11.098(5) _cell_length_c 17.391(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2120.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1635 _cell_measurement_theta_min 3.5001 _cell_measurement_theta_max 28.9174 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.293 _exptl_crystal_size_mid 0.158 _exptl_crystal_size_min 0.098 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99475 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3280 _diffrn_standards_number 6433 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5383 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3476 _reflns_number_gt 1723 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SIR92 (Altomare, 1993)' _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^)+(0.0307P)^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 0.0011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(18) _refine_ls_number_reflns 3476 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0706 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 0.804 _refine_ls_restrained_S_all 0.804 _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 0.46635(15) 0.84274(14) 0.65498(8) 0.0781(5) Uani 1 1 d . . . C8 C 0.3902(2) 0.91891(18) 1.02197(12) 0.0581(6) Uani 1 1 d . . . H8 H 0.4703 0.8810 1.0276 0.070 Uiso 1 1 calc R . . C10 C 0.3605(2) 0.8430(2) 0.88529(13) 0.0569(6) Uani 1 1 d . . . C4 C 0.4763(2) 0.93371(19) 0.78273(13) 0.0628(6) Uani 1 1 d . . . H4 H 0.5295 0.9934 0.7660 0.075 Uiso 1 1 calc R . . C9 C 0.3142(3) 0.8393(2) 0.96743(14) 0.0643(7) Uani 1 1 d . . . C1 C 0.3205(2) 0.7579(2) 0.83239(15) 0.0702(7) Uani 1 1 d . . . H1 H 0.2669 0.6981 0.8485 0.084 Uiso 1 1 calc R . . C5 C 0.4384(2) 0.93225(18) 0.85947(12) 0.0561(6) Uani 1 1 d . . . C6 C 0.4854(2) 1.02896(19) 0.91281(12) 0.0675(7) Uani 1 1 d . . . H6A H 0.4860 1.1054 0.8857 0.081 Uiso 1 1 calc R . . H6B H 0.5686 1.0101 0.9270 0.081 Uiso 1 1 calc R . . C2 C 0.3580(2) 0.7596(2) 0.75697(15) 0.0712(7) Uani 1 1 d . . . H2 H 0.3307 0.7008 0.7230 0.085 Uiso 1 1 calc R . . C3 C 0.4358(2) 0.8480(2) 0.73183(13) 0.0612(6) Uani 1 1 d . . . C14 C 0.3313(3) 0.9234(2) 1.10176(14) 0.0659(7) Uani 1 1 d . . . C7 C 0.4095(2) 1.04177(18) 0.98540(12) 0.0673(7) Uani 1 1 d . . . H7A H 0.3314 1.0774 0.9729 0.081 Uiso 1 1 calc R . . H7B H 0.4508 1.0946 1.0214 0.081 Uiso 1 1 calc R . . C21 C 0.5689(3) 0.90288(19) 0.54252(14) 0.0660(7) Uani 1 1 d . . . C20 C 0.5504(2) 0.9298(2) 0.62586(12) 0.0734(7) Uani 1 1 d . . . H20A H 0.6271 0.9245 0.6533 0.088 Uiso 1 1 calc R . . H20B H 0.5180 1.0105 0.6323 0.088 Uiso 1 1 calc R . . C26 C 0.6785(3) 0.8665(2) 0.51428(16) 0.0757(8) Uani 1 1 d . . . H26 H 0.7437 0.8572 0.5479 0.091 Uiso 1 1 calc R . . C13 C 0.3121(3) 0.7982(2) 1.13889(14) 0.0725(7) Uani 1 1 d . . . C11 C 0.3002(3) 0.7146(2) 1.00107(14) 0.0852(8) Uani 1 1 d . . . H11A H 0.3794 0.6764 1.0043 0.102 Uiso 1 1 calc R . . H11B H 0.2495 0.6663 0.9673 0.102 Uiso 1 1 calc R . . C15 C 0.3924(3) 1.0139(2) 1.15705(13) 0.0768(7) Uani 1 1 d . . . H15A H 0.3710 1.0949 1.1411 0.092 Uiso 1 1 calc R . . H15B H 0.3596 1.0017 1.2082 0.092 Uiso 1 1 calc R . . C17 C 0.2299(4) 0.8129(3) 1.2087(2) 0.0945(10) Uani 1 1 d . . . C16 C 0.5238(3) 1.0048(2) 1.16082(15) 0.0762(8) Uani 1 1 d . . . C25 C 0.6952(3) 0.8433(2) 0.43707(18) 0.0888(8) Uani 1 1 d . . . H25 H 0.7701 0.8163 0.4191 0.107 Uiso 1 1 calc R . . C24 C 0.6008(4) 0.8603(3) 0.38753(16) 0.0957(9) Uani 1 1 d . . . H24 H 0.6118 0.8475 0.3351 0.115 Uiso 1 1 calc R . . N1 N 0.6260(3) 0.9988(2) 1.16398(16) 0.1143(10) Uani 1 1 d . . . C12 C 0.2432(3) 0.7188(2) 1.08043(14) 0.0932(9) Uani 1 1 d . . . H12A H 0.2387 0.6373 1.1005 0.112 Uiso 1 1 calc R . . H12B H 0.1605 0.7487 1.0757 0.112 Uiso 1 1 calc R . . C18 C 0.2490(4) 0.7837(3) 1.2784(3) 0.1096(12) Uani 1 1 d . . . C19 C 0.4320(3) 0.7373(2) 1.16038(13) 0.0921(9) Uani 1 1 d . . . H19A H 0.4159 0.6583 1.1804 0.138 Uiso 1 1 calc R . . H19B H 0.4731 0.7845 1.1987 0.138 Uiso 1 1 calc R . . H19C H 0.4826 0.7307 1.1155 0.138 Uiso 1 1 calc R . . C22 C 0.4759(3) 0.9164(3) 0.49200(17) 0.1062(10) Uani 1 1 d . . . H22 H 0.3999 0.9401 0.5101 0.127 Uiso 1 1 calc R . . C23 C 0.4912(4) 0.8958(3) 0.41434(18) 0.1174(12) Uani 1 1 d . . . H23 H 0.4264 0.9063 0.3806 0.141 Uiso 1 1 calc R . . H14 H 0.2519(17) 0.9549(15) 1.0954(10) 0.047(6) Uiso 1 1 d . . . H99 H 0.2359(18) 0.8735(16) 0.9677(11) 0.054(7) Uiso 1 1 d . . . H17 H 0.154(3) 0.855(3) 1.1967(18) 0.149(15) Uiso 1 1 d . . . H18A H 0.178(3) 0.799(2) 1.3199(17) 0.133(12) Uiso 1 1 d . . . H18B H 0.328(3) 0.757(3) 1.2889(17) 0.115(13) 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 O1 0.0867(13) 0.0820(11) 0.0655(11) -0.0129(9) 0.0052(10) -0.0140(11) C8 0.0590(16) 0.0509(14) 0.0645(15) -0.0007(13) 0.0025(13) 0.0039(12) C10 0.0538(16) 0.0487(13) 0.0681(16) -0.0037(13) -0.0025(13) -0.0017(13) C4 0.0638(16) 0.0553(14) 0.0692(17) -0.0045(13) 0.0030(15) -0.0046(13) C9 0.0634(19) 0.0599(16) 0.0696(18) -0.0012(14) -0.0017(16) 0.0018(16) C1 0.0678(17) 0.0660(17) 0.0768(18) -0.0017(15) 0.0003(17) -0.0164(14) C5 0.0554(15) 0.0493(14) 0.0635(16) -0.0049(12) -0.0006(13) 0.0022(12) C6 0.0794(18) 0.0524(14) 0.0708(16) -0.0060(12) 0.0035(15) -0.0046(13) C2 0.0685(17) 0.0726(17) 0.0724(19) -0.0158(14) -0.0064(15) -0.0149(15) C3 0.0625(17) 0.0628(15) 0.0584(16) -0.0081(14) 0.0023(14) -0.0024(15) C14 0.0583(18) 0.0667(17) 0.0727(18) 0.0008(14) -0.0021(15) 0.0064(15) C7 0.0854(19) 0.0520(14) 0.0645(15) -0.0061(12) 0.0041(15) 0.0014(13) C21 0.071(2) 0.0608(14) 0.0665(16) -0.0040(14) -0.0003(17) 0.0027(15) C20 0.082(2) 0.0670(16) 0.0711(17) -0.0094(14) 0.0072(16) -0.0041(15) C26 0.073(2) 0.0831(19) 0.0712(18) -0.0060(14) 0.0031(17) -0.0146(17) C13 0.0764(19) 0.0663(16) 0.0747(17) 0.0083(14) 0.0027(17) -0.0023(16) C11 0.105(2) 0.0718(18) 0.0790(18) -0.0021(16) -0.0012(18) -0.0268(17) C15 0.098(2) 0.0610(15) 0.0712(17) -0.0060(14) 0.0130(17) 0.0054(16) C17 0.110(3) 0.105(2) 0.068(2) 0.0220(19) 0.015(2) -0.007(2) C16 0.092(2) 0.0689(17) 0.0680(18) -0.0135(14) 0.007(2) -0.014(2) C25 0.087(2) 0.0924(19) 0.087(2) -0.0108(18) 0.024(2) -0.0202(18) C24 0.126(3) 0.099(2) 0.0624(19) -0.0023(16) 0.002(2) -0.008(2) N1 0.0984(19) 0.1070(19) 0.137(2) -0.0198(17) -0.002(2) -0.0223(19) C12 0.110(2) 0.0888(19) 0.0810(18) 0.0088(17) 0.0009(19) -0.0343(18) C18 0.116(3) 0.114(3) 0.099(3) 0.009(2) 0.022(3) -0.007(3) C19 0.110(2) 0.0706(17) 0.0960(19) 0.0132(15) -0.005(2) 0.0034(18) C22 0.089(2) 0.152(3) 0.078(2) -0.0279(19) -0.0077(19) 0.037(2) C23 0.118(3) 0.153(3) 0.082(2) -0.010(2) -0.022(2) 0.035(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 C3 1.379(2) . ? O1 C20 1.429(3) . ? C8 C7 1.519(3) . ? C8 C14 1.532(3) . ? C8 C9 1.542(3) . ? C8 H8 0.9800 . ? C10 C5 1.384(3) . ? C10 C1 1.390(3) . ? C10 C9 1.517(3) . ? C4 C3 1.373(3) . ? C4 C5 1.398(3) . ? C4 H4 0.9300 . ? C9 C11 1.510(3) . ? C9 H99 0.941(19) . ? C1 C2 1.375(3) . ? C1 H1 0.9300 . ? C5 C6 1.509(3) . ? C6 C7 1.519(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C2 C3 1.373(3) . ? C2 H2 0.9300 . ? C14 C15 1.544(3) . ? C14 C13 1.546(3) . ? C14 H14 0.946(17) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C21 C22 1.356(3) . ? C21 C26 1.361(3) . ? C21 C20 1.494(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C26 C25 1.380(3) . ? C26 H26 0.9300 . ? C13 C17 1.522(4) . ? C13 C19 1.528(3) . ? C13 C12 1.544(3) . ? C11 C12 1.516(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C15 C16 1.448(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 C18 1.272(4) . ? C17 H17 0.97(3) . ? C16 N1 1.126(3) . ? C25 C24 1.362(4) . ? C25 H25 0.9300 . ? C24 C23 1.349(4) . ? C24 H24 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C18 H18A 1.07(3) . ? C18 H18B 0.94(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C22 C23 1.380(3) . ? C22 H22 0.9300 . ? C23 H23 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 C3 O1 C20 118.17(18) . . ? C7 C8 C14 114.16(18) . . ? C7 C8 C9 109.42(18) . . ? C14 C8 C9 110.29(19) . . ? C7 C8 H8 107.6 . . ? C14 C8 H8 107.6 . . ? C9 C8 H8 107.6 . . ? C5 C10 C1 117.9(2) . . ? C5 C10 C9 122.2(2) . . ? C1 C10 C9 119.9(2) . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C11 C9 C10 115.1(2) . . ? C11 C9 C8 110.0(2) . . ? C10 C9 C8 112.5(2) . . ? C11 C9 H99 106.0(12) . . ? C10 C9 H99 107.4(12) . . ? C8 C9 H99 105.1(11) . . ? C2 C1 C10 121.8(2) . . ? C2 C1 H1 119.1 . . ? C10 C1 H1 119.1 . . ? C10 C5 C4 120.1(2) . . ? C10 C5 C6 121.4(2) . . ? C4 C5 C6 118.5(2) . . ? C5 C6 C7 112.94(19) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 O1 115.4(2) . . ? C4 C3 O1 125.1(2) . . ? C8 C14 C15 113.6(2) . . ? C8 C14 C13 114.01(19) . . ? C15 C14 C13 112.6(2) . . ? C8 C14 H14 107.2(11) . . ? C15 C14 H14 103.5(11) . . ? C13 C14 H14 104.8(11) . . ? C6 C7 C8 109.90(18) . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C22 C21 C26 117.7(2) . . ? C22 C21 C20 120.3(3) . . ? C26 C21 C20 122.0(3) . . ? O1 C20 C21 107.26(19) . . ? O1 C20 H20A 110.3 . . ? C21 C20 H20A 110.3 . . ? O1 C20 H20B 110.3 . . ? C21 C20 H20B 110.3 . . ? H20A C20 H20B 108.5 . . ? C21 C26 C25 121.6(3) . . ? C21 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C17 C13 C19 111.3(2) . . ? C17 C13 C12 107.3(2) . . ? C19 C13 C12 109.4(2) . . ? C17 C13 C14 108.5(2) . . ? C19 C13 C14 112.5(2) . . ? C12 C13 C14 107.7(2) . . ? C9 C11 C12 111.5(2) . . ? C9 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C9 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C16 C15 C14 114.6(2) . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C18 C17 C13 129.5(4) . . ? C18 C17 H17 118(2) . . ? C13 C17 H17 112.7(19) . . ? N1 C16 C15 179.4(3) . . ? C24 C25 C26 119.2(3) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C23 C24 C25 120.1(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C11 C12 C13 114.5(2) . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C17 C18 H18A 118.8(16) . . ? C17 C18 H18B 114.8(19) . . ? H18A C18 H18B 126(3) . . ? C13 C19 H19A 109.5 . . ? C13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C22 C23 121.6(3) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C24 C23 C22 119.7(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? 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 C5 C10 C9 C11 -143.9(2) . . . . ? C1 C10 C9 C11 39.0(3) . . . . ? C5 C10 C9 C8 -16.8(3) . . . . ? C1 C10 C9 C8 166.0(2) . . . . ? C7 C8 C9 C11 176.9(2) . . . . ? C14 C8 C9 C11 -56.7(3) . . . . ? C7 C8 C9 C10 47.2(3) . . . . ? C14 C8 C9 C10 173.5(2) . . . . ? C5 C10 C1 C2 1.2(3) . . . . ? C9 C10 C1 C2 178.5(2) . . . . ? C1 C10 C5 C4 -1.2(3) . . . . ? C9 C10 C5 C4 -178.4(2) . . . . ? C1 C10 C5 C6 179.4(2) . . . . ? C9 C10 C5 C6 2.2(3) . . . . ? C3 C4 C5 C10 0.9(3) . . . . ? C3 C4 C5 C6 -179.7(2) . . . . ? C10 C5 C6 C7 -18.7(3) . . . . ? C4 C5 C6 C7 161.91(19) . . . . ? C10 C1 C2 C3 -0.9(4) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C1 C2 C3 O1 -179.1(2) . . . . ? C5 C4 C3 C2 -0.5(3) . . . . ? C5 C4 C3 O1 179.0(2) . . . . ? C20 O1 C3 C2 -177.8(2) . . . . ? C20 O1 C3 C4 2.6(3) . . . . ? C7 C8 C14 C15 -49.0(3) . . . . ? C9 C8 C14 C15 -172.7(2) . . . . ? C7 C8 C14 C13 -179.9(2) . . . . ? C9 C8 C14 C13 56.5(3) . . . . ? C5 C6 C7 C8 49.6(2) . . . . ? C14 C8 C7 C6 171.31(19) . . . . ? C9 C8 C7 C6 -64.6(2) . . . . ? C3 O1 C20 C21 179.2(2) . . . . ? C22 C21 C20 O1 66.3(3) . . . . ? C26 C21 C20 O1 -115.0(2) . . . . ? C22 C21 C26 C25 -0.4(4) . . . . ? C20 C21 C26 C25 -179.2(2) . . . . ? C8 C14 C13 C17 -168.1(2) . . . . ? C15 C14 C13 C17 60.5(3) . . . . ? C8 C14 C13 C19 68.3(3) . . . . ? C15 C14 C13 C19 -63.1(3) . . . . ? C8 C14 C13 C12 -52.3(3) . . . . ? C15 C14 C13 C12 176.3(2) . . . . ? C10 C9 C11 C12 -175.0(2) . . . . ? C8 C9 C11 C12 56.7(3) . . . . ? C8 C14 C15 C16 -48.7(3) . . . . ? C13 C14 C15 C16 82.8(3) . . . . ? C19 C13 C17 C18 0.9(5) . . . . ? C12 C13 C17 C18 120.5(4) . . . . ? C14 C13 C17 C18 -123.4(4) . . . . ? C14 C15 C16 N1 159(100) . . . . ? C21 C26 C25 C24 1.9(4) . . . . ? C26 C25 C24 C23 -2.1(4) . . . . ? C9 C11 C12 C13 -56.3(3) . . . . ? C17 C13 C12 C11 168.5(3) . . . . ? C19 C13 C12 C11 -70.7(3) . . . . ? C14 C13 C12 C11 51.9(3) . . . . ? C26 C21 C22 C23 -0.8(4) . . . . ? C20 C21 C22 C23 178.0(3) . . . . ? C25 C24 C23 C22 0.9(5) . . . . ? C21 C22 C23 C24 0.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.086 _refine_diff_density_min -0.070 _refine_diff_density_rms 0.019 data_I _database_code_depnum_ccdc_archive 'CCDC 901000' _cell_length_a 8.099 _cell_length_b 10.195 _cell_length_c 24.458 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z -x,1/2+y,1/2-z 1/2+x,1/2-y,-z loop_ _atom_site_type_symbol _atom_site_label _atom_site_Cartn_x _atom_site_Cartn_y _atom_site_Cartn_z C C1 12.94903 -4.17612 18.94900 O O2 13.54204 -3.32406 14.23871 C C3 10.73294 -4.02259 20.20306 H H4 10.38951 -5.04733 20.01530 C C5 10.85975 -3.64428 17.63269 C C6 10.13046 -3.55394 21.55993 H H7 10.55295 -2.55718 21.76718 C C8 10.55727 -4.46667 22.73956 H H9 10.38071 -5.51958 22.49079 H H10 11.63028 -4.35559 22.93162 C C11 10.28918 -3.12294 19.01662 H H12 10.74050 -2.13455 19.20049 N N13 8.69476 -3.37143 23.98436 C C14 12.34015 -4.01810 17.76155 C C15 9.82316 -4.13403 23.98442 N N16 10.05765 -4.50449 25.22361 C C17 13.12321 -4.20174 16.47784 H H18 12.80573 -5.12929 15.98460 H H19 14.19073 -4.34726 16.68418 C C20 12.94936 -3.02096 15.51737 H H21 13.40423 -2.11244 15.93485 C C22 8.76428 -2.89532 19.00141 H H23 8.50529 -2.14319 18.24821 H H24 8.23406 -3.80933 18.71920 C C25 10.71595 -2.50338 16.58113 H H26 9.65924 -2.33716 16.34058 H H27 11.08749 -1.56170 17.00766 C C28 11.46455 -2.75227 15.27203 H H29 11.01378 -3.58793 14.72227 H H30 11.35613 -1.88143 14.61341 O O31 15.61962 -2.77949 15.05854 C C32 12.27353 -4.05421 20.27607 H H33 12.65135 -3.14662 20.76315 H H34 12.58836 -4.90398 20.89306 C C35 8.57667 -3.37272 21.50502 N N36 9.05228 -3.94097 25.98211 N N37 8.21617 -3.24051 25.22453 C C38 10.09232 -4.89518 17.14012 H H39 10.53558 -5.32726 16.23670 H H40 9.05433 -4.65828 16.88488 H H41 10.08056 -5.68842 17.89466 C C42 8.23083 -2.41372 20.34800 H H43 7.14367 -2.28176 20.27773 H H44 8.64811 -1.41849 20.55169 C C45 7.83191 -4.71653 21.30816 H H46 7.95245 -5.38725 22.16471 H H47 8.17671 -5.26222 20.42573 H H48 6.75582 -4.54616 21.18590 C C49 8.09570 -2.73308 22.83802 H H50 8.38624 -1.67710 22.89628 H H51 7.00653 -2.79575 22.94239 C C52 14.89078 -3.16342 14.15530 C C53 15.36337 -3.48683 12.77099 H H54 15.16398 -2.64194 12.10800 H H55 14.86284 -4.38635 12.40217 H H56 16.43819 -3.68788 12.79439 H H57 14.01060 -4.41770 18.98430 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 901001' #TrackingRef 'Compound 14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 N4 O' _chemical_formula_weight 414.54 _chemical_absolute_configuration syn 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.039(5) _cell_length_b 12.320(5) _cell_length_c 9.996(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 93.034(5) _cell_angle_gamma 90.000(5) _cell_volume 1111.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1517 _cell_measurement_theta_min 3.5846 _cell_measurement_theta_max 72.1059 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.282 _exptl_crystal_size_mid 0.185 _exptl_crystal_size_min 0.023 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95325 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3280 _diffrn_standards_number 3840 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3829 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.43 _diffrn_reflns_theta_max 72.25 _reflns_number_total 2627 _reflns_number_gt 2231 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SIR92 (Altomare, 1993)' _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^)+(0.0543P)^2^+0.0312P] 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 0.0017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(4) _refine_ls_number_reflns 2627 _refine_ls_number_parameters 374 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0941 _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 O1 O 0.6070(2) 0.46592(16) 0.3132(2) 0.0665(6) Uani 1 1 d . . . C14 C 0.8574(3) -0.0887(2) 0.6379(3) 0.0543(7) Uani 1 1 d . . . C20 C 0.6267(3) 0.5745(2) 0.3608(3) 0.0570(7) Uani 1 1 d . . . C13 C 0.8970(3) -0.0677(2) 0.7892(3) 0.0528(6) Uani 1 1 d . . . C1 C 0.8287(3) 0.3119(2) 0.5674(3) 0.0523(6) Uani 1 1 d . . . C2 C 0.7581(3) 0.4001(3) 0.5065(3) 0.0556(6) Uani 1 1 d . . . C5 C 0.7368(3) 0.1938(2) 0.3929(3) 0.0582(7) Uani 1 1 d . . . N1 N 0.8987(3) -0.2657(2) 0.8077(3) 0.0688(7) Uani 1 1 d . . . C12 C 1.0014(4) 0.0292(3) 0.7983(3) 0.0631(8) Uani 1 1 d . . . C10 C 0.8222(3) 0.2084(2) 0.5130(3) 0.0523(6) Uani 1 1 d . . . C4 C 0.6670(4) 0.2822(2) 0.3317(3) 0.0601(7) Uani 1 1 d . . . C21 C 0.5698(3) 0.6513(2) 0.2528(3) 0.0551(7) Uani 1 1 d . . . C3 C 0.6780(3) 0.3848(2) 0.3861(3) 0.0557(7) Uani 1 1 d . . . C11 C 0.9384(4) 0.1305(3) 0.7300(3) 0.0639(8) Uani 1 1 d . . . C9 C 0.8953(3) 0.1109(2) 0.5823(3) 0.0533(7) Uani 1 1 d . . . N4 N 0.7480(4) -0.3774(2) 0.7042(3) 0.0921(10) Uani 1 1 d . . . C8 C 0.7965(3) 0.0115(2) 0.5619(3) 0.0538(6) Uani 1 1 d . . . C16 C 0.7962(4) -0.2758(2) 0.7081(3) 0.0723(9) Uani 1 1 d . . . C17A C 0.9832(4) -0.1672(3) 0.8460(3) 0.0656(8) Uani 1 1 d . . . C22 C 0.4965(3) 0.7450(3) 0.2868(3) 0.0628(7) Uani 1 1 d . . . C26 C 0.5928(4) 0.6318(3) 0.1188(3) 0.0659(8) Uani 1 1 d . . . C23 C 0.4481(4) 0.8193(3) 0.1890(4) 0.0742(9) Uani 1 1 d . . . C6 C 0.7168(5) 0.0830(3) 0.3312(3) 0.0864(11) Uani 1 1 d . . . H6A H 0.6117 0.0713 0.3123 0.104 Uiso 1 1 calc R . . H6B H 0.7636 0.0830 0.2461 0.104 Uiso 1 1 calc R . . N2 N 0.9179(4) -0.3635(2) 0.8679(3) 0.0902(10) Uani 1 1 d . . . C7 C 0.7756(5) -0.0098(3) 0.4107(3) 0.0778(10) Uani 1 1 d . . . H7A H 0.8704 -0.0305 0.3773 0.093 Uiso 1 1 calc R . . H7B H 0.7088 -0.0708 0.3966 0.093 Uiso 1 1 calc R . . C18 C 0.7585(4) -0.0465(3) 0.8667(3) 0.0737(8) Uani 1 1 d . . . H18A H 0.7871 -0.0183 0.9538 0.111 Uiso 1 1 calc R . . H18B H 0.7051 -0.1132 0.8761 0.111 Uiso 1 1 calc R . . H18C H 0.6964 0.0052 0.8189 0.111 Uiso 1 1 calc R . . C15 C 0.7505(5) -0.1848(3) 0.6192(4) 0.0792(11) Uani 1 1 d . . . N3 N 0.8259(5) -0.4291(3) 0.8059(3) 0.1021(11) Uani 1 1 d . . . C24 C 0.4717(4) 0.7988(3) 0.0573(4) 0.0778(10) Uani 1 1 d . . . C19 C 1.0191(7) -0.1670(4) 0.9951(5) 0.0976(15) Uani 1 1 d . . . C25 C 0.5433(5) 0.7053(3) 0.0221(4) 0.0810(10) Uani 1 1 d . . . H14 H 0.956(3) -0.114(2) 0.599(2) 0.052(7) Uiso 1 1 d . . . H8 H 0.692(3) 0.033(2) 0.602(3) 0.062(8) Uiso 1 1 d . . . H1 H 0.883(3) 0.326(2) 0.652(3) 0.050(7) Uiso 1 1 d . . . H2 H 0.766(4) 0.469(3) 0.548(4) 0.087(11) Uiso 1 1 d . . . H12A H 1.030(3) 0.042(3) 0.890(3) 0.074(9) Uiso 1 1 d . . . H11A H 0.845(3) 0.157(3) 0.774(3) 0.069(9) Uiso 1 1 d . . . H25 H 0.566(4) 0.686(3) -0.066(4) 0.098(12) Uiso 1 1 d . . . H19A H 1.075(5) -0.108(3) 1.020(4) 0.104(15) Uiso 1 1 d . . . H20A H 0.740(3) 0.594(2) 0.384(3) 0.059(8) Uiso 1 1 d . . . H20B H 0.578(3) 0.581(3) 0.443(3) 0.073(9) Uiso 1 1 d . . . H4 H 0.608(3) 0.271(2) 0.250(3) 0.063(8) Uiso 1 1 d . . . H23 H 0.406(4) 0.886(3) 0.223(4) 0.102(12) Uiso 1 1 d . . . H15A H 0.649(6) -0.165(4) 0.636(5) 0.141(19) Uiso 1 1 d . . . H19B H 1.089(5) -0.228(4) 1.012(4) 0.115(15) Uiso 1 1 d . . . H17 H 1.075(3) -0.170(3) 0.806(3) 0.072(10) Uiso 1 1 d . . . H24 H 0.438(4) 0.849(3) -0.012(4) 0.093(12) Uiso 1 1 d . . . H11B H 1.014(4) 0.192(3) 0.740(4) 0.101(13) Uiso 1 1 d . . . H26 H 0.639(3) 0.567(3) 0.098(3) 0.080(10) Uiso 1 1 d . . . H15B H 0.750(4) -0.210(3) 0.530(4) 0.097(13) Uiso 1 1 d . . . H9 H 0.992(3) 0.090(3) 0.536(3) 0.075(9) Uiso 1 1 d . . . H22 H 0.491(4) 0.759(3) 0.378(3) 0.074(10) Uiso 1 1 d . . . H12B H 1.094(4) 0.008(3) 0.755(3) 0.080(10) Uiso 1 1 d . . . H19C H 0.937(5) -0.181(4) 1.045(4) 0.112(18) 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 O1 0.0771(12) 0.0509(11) 0.0687(13) 0.0067(10) -0.0210(10) -0.0058(10) C14 0.0614(15) 0.0462(15) 0.0545(16) -0.0007(13) -0.0033(13) 0.0034(12) C20 0.0627(16) 0.0506(15) 0.0569(17) 0.0061(14) -0.0039(14) 0.0010(13) C13 0.0576(14) 0.0501(14) 0.0500(15) 0.0050(12) -0.0033(11) 0.0037(12) C1 0.0613(15) 0.0467(14) 0.0479(15) 0.0006(12) -0.0052(12) -0.0092(12) C2 0.0651(16) 0.0491(15) 0.0522(15) 0.0038(13) -0.0009(12) -0.0064(13) C5 0.0777(18) 0.0519(16) 0.0442(14) 0.0007(13) -0.0038(13) -0.0049(13) N1 0.0922(19) 0.0461(14) 0.0671(16) 0.0092(12) -0.0054(14) 0.0081(13) C12 0.0740(19) 0.0571(17) 0.0562(18) 0.0058(15) -0.0164(16) -0.0062(15) C10 0.0586(15) 0.0521(15) 0.0457(14) 0.0032(12) -0.0013(11) -0.0061(12) C4 0.0789(19) 0.0529(16) 0.0468(15) 0.0014(13) -0.0128(14) -0.0052(14) C21 0.0520(14) 0.0519(16) 0.0608(17) 0.0077(13) -0.0025(12) -0.0028(12) C3 0.0591(15) 0.0502(15) 0.0571(16) 0.0123(13) -0.0027(13) -0.0025(12) C11 0.082(2) 0.0537(17) 0.0541(17) 0.0022(14) -0.0169(15) -0.0047(16) C9 0.0613(15) 0.0467(15) 0.0513(16) 0.0034(12) -0.0029(13) 0.0000(12) N4 0.143(3) 0.0494(16) 0.081(2) 0.0035(15) -0.0182(19) -0.0114(18) C8 0.0622(15) 0.0461(15) 0.0520(16) 0.0003(12) -0.0063(13) -0.0006(12) C16 0.103(2) 0.0447(17) 0.068(2) 0.0004(15) -0.0050(18) -0.0026(17) C17A 0.0698(18) 0.0556(17) 0.070(2) 0.0106(16) -0.0053(15) 0.0052(16) C22 0.0677(17) 0.0593(18) 0.0614(19) 0.0055(15) 0.0029(14) 0.0099(14) C26 0.0785(19) 0.0573(18) 0.0621(19) 0.0096(15) 0.0041(15) 0.0114(16) C23 0.085(2) 0.0584(19) 0.079(2) 0.0076(17) 0.0046(17) 0.0180(17) C6 0.147(3) 0.0584(19) 0.0512(17) -0.0065(15) -0.022(2) 0.004(2) N2 0.131(3) 0.0506(16) 0.087(2) 0.0142(16) -0.0125(19) 0.0091(18) C7 0.122(3) 0.0486(18) 0.0608(18) -0.0034(14) -0.0190(19) 0.0031(17) C18 0.083(2) 0.071(2) 0.069(2) 0.0057(17) 0.0141(16) 0.0095(17) C15 0.106(3) 0.0495(19) 0.078(2) 0.0069(17) -0.028(2) -0.0109(19) N3 0.164(3) 0.0493(16) 0.090(2) 0.0047(17) -0.016(2) -0.001(2) C24 0.087(2) 0.075(2) 0.072(2) 0.0227(19) 0.0037(18) 0.0117(18) C19 0.130(4) 0.071(3) 0.087(3) 0.020(2) -0.039(3) -0.005(3) C25 0.099(3) 0.086(3) 0.059(2) 0.0117(19) 0.0086(18) 0.014(2) _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 C3 1.376(3) . ? O1 C20 1.428(3) . ? C14 C15 1.533(4) . ? C14 C8 1.536(4) . ? C14 C13 1.557(4) . ? C14 H14 1.04(3) . ? C20 C21 1.506(4) . ? C20 H20A 1.06(3) . ? C20 H20B 0.96(3) . ? C13 C12 1.521(4) . ? C13 C18 1.529(4) . ? C13 C17A 1.545(4) . ? C1 C2 1.385(4) . ? C1 C10 1.386(4) . ? C1 H1 0.97(3) . ? C2 C3 1.384(4) . ? C2 H2 0.95(4) . ? C5 C4 1.384(4) . ? C5 C10 1.404(4) . ? C5 C6 1.505(4) . ? N1 C16 1.329(4) . ? N1 N2 1.354(4) . ? N1 C17A 1.473(4) . ? C12 C11 1.519(4) . ? C12 H12A 0.95(3) . ? C12 H12B 0.99(4) . ? C10 C9 1.521(4) . ? C4 C3 1.379(4) . ? C4 H4 0.97(3) . ? C21 C22 1.382(4) . ? C21 C26 1.388(4) . ? C11 C9 1.526(4) . ? C11 H11A 1.02(3) . ? C11 H11B 1.02(4) . ? C9 C8 1.522(4) . ? C9 H9 1.04(3) . ? N4 C16 1.326(4) . ? N4 N3 1.363(4) . ? C8 C7 1.536(4) . ? C8 H8 1.08(3) . ? C16 C15 1.476(5) . ? C17A C19 1.508(6) . ? C17A H17 0.94(3) . ? C22 C23 1.393(4) . ? C22 H22 0.93(3) . ? C26 C25 1.382(4) . ? C26 H26 0.93(3) . ? C23 C24 1.368(5) . ? C23 H23 0.98(4) . ? C6 C7 1.476(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N2 N3 1.294(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C15 H15A 0.97(5) . ? C15 H15B 0.94(4) . ? C24 C25 1.376(5) . ? C24 H24 0.97(4) . ? C19 H19A 0.91(4) . ? C19 H19B 0.99(5) . ? C19 H19C 0.93(4) . ? C25 H25 0.95(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 O1 C20 117.2(2) . . ? C15 C14 C8 110.7(2) . . ? C15 C14 C13 111.0(3) . . ? C8 C14 C13 113.9(2) . . ? C15 C14 H14 105.9(15) . . ? C8 C14 H14 110.3(15) . . ? C13 C14 H14 104.7(14) . . ? O1 C20 C21 108.5(2) . . ? O1 C20 H20A 113.0(16) . . ? C21 C20 H20A 107.5(16) . . ? O1 C20 H20B 108(2) . . ? C21 C20 H20B 113.8(19) . . ? H20A C20 H20B 106(2) . . ? C12 C13 C18 111.0(3) . . ? C12 C13 C17A 107.5(2) . . ? C18 C13 C17A 111.0(3) . . ? C12 C13 C14 107.4(2) . . ? C18 C13 C14 111.6(2) . . ? C17A C13 C14 108.1(2) . . ? C2 C1 C10 122.7(3) . . ? C2 C1 H1 116.0(16) . . ? C10 C1 H1 121.2(16) . . ? C3 C2 C1 118.9(3) . . ? C3 C2 H2 122(2) . . ? C1 C2 H2 119(2) . . ? C4 C5 C10 119.7(3) . . ? C4 C5 C6 119.3(2) . . ? C10 C5 C6 121.0(3) . . ? C16 N1 N2 108.5(3) . . ? C16 N1 C17A 127.1(2) . . ? N2 N1 C17A 124.4(3) . . ? C11 C12 C13 113.7(2) . . ? C11 C12 H12A 112(2) . . ? C13 C12 H12A 109(2) . . ? C11 C12 H12B 109(2) . . ? C13 C12 H12B 108(2) . . ? H12A C12 H12B 106(3) . . ? C1 C10 C5 117.6(3) . . ? C1 C10 C9 122.7(2) . . ? C5 C10 C9 119.6(2) . . ? C3 C4 C5 121.7(2) . . ? C3 C4 H4 119.3(19) . . ? C5 C4 H4 119.0(19) . . ? C22 C21 C26 118.7(3) . . ? C22 C21 C20 119.9(3) . . ? C26 C21 C20 121.3(3) . . ? O1 C3 C4 115.8(2) . . ? O1 C3 C2 124.8(3) . . ? C4 C3 C2 119.5(3) . . ? C12 C11 C9 112.0(3) . . ? C12 C11 H11A 111.4(18) . . ? C9 C11 H11A 106.8(16) . . ? C12 C11 H11B 109(2) . . ? C9 C11 H11B 110(2) . . ? H11A C11 H11B 107(3) . . ? C10 C9 C8 109.7(2) . . ? C10 C9 C11 113.4(2) . . ? C8 C9 C11 112.1(2) . . ? C10 C9 H9 110.0(18) . . ? C8 C9 H9 104.3(18) . . ? C11 C9 H9 107.0(16) . . ? C16 N4 N3 105.3(3) . . ? C9 C8 C14 112.8(2) . . ? C9 C8 C7 108.1(2) . . ? C14 C8 C7 111.8(2) . . ? C9 C8 H8 105.9(15) . . ? C14 C8 H8 108.1(15) . . ? C7 C8 H8 110.0(14) . . ? N4 C16 N1 109.0(3) . . ? N4 C16 C15 128.2(3) . . ? N1 C16 C15 122.8(3) . . ? N1 C17A C19 109.9(3) . . ? N1 C17A C13 108.3(2) . . ? C19 C17A C13 116.1(3) . . ? N1 C17A H17 108(2) . . ? C19 C17A H17 105.6(19) . . ? C13 C17A H17 108(2) . . ? C21 C22 C23 120.9(3) . . ? C21 C22 H22 117(2) . . ? C23 C22 H22 122(2) . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 123(2) . . ? C21 C26 H26 117(2) . . ? C24 C23 C22 119.6(3) . . ? C24 C23 H23 125(2) . . ? C22 C23 H23 115(2) . . ? C7 C6 C5 116.8(3) . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6A 108.1 . . ? C7 C6 H6B 108.1 . . ? C5 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? N3 N2 N1 106.2(3) . . ? C6 C7 C8 114.8(3) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C15 C14 111.0(3) . . ? C16 C15 H15A 109(3) . . ? C14 C15 H15A 112(3) . . ? C16 C15 H15B 108(3) . . ? C14 C15 H15B 110(3) . . ? H15A C15 H15B 107(4) . . ? N2 N3 N4 111.0(3) . . ? C23 C24 C25 120.1(3) . . ? C23 C24 H24 120(2) . . ? C25 C24 H24 119(2) . . ? C17A C19 H19A 111(3) . . ? C17A C19 H19B 106(3) . . ? H19A C19 H19B 103(3) . . ? C17A C19 H19C 113(3) . . ? H19A C19 H19C 117(4) . . ? H19B C19 H19C 107(4) . . ? C24 C25 C26 120.5(4) . . ? C24 C25 H25 125(2) . . ? C26 C25 H25 114(2) . . ? 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 C3 O1 C20 C21 167.6(2) . . . . ? C15 C14 C13 C12 -179.4(3) . . . . ? C8 C14 C13 C12 -53.7(3) . . . . ? C15 C14 C13 C18 -57.6(3) . . . . ? C8 C14 C13 C18 68.1(3) . . . . ? C15 C14 C13 C17A 64.9(3) . . . . ? C8 C14 C13 C17A -169.4(2) . . . . ? C10 C1 C2 C3 -0.2(4) . . . . ? C18 C13 C12 C11 -65.6(4) . . . . ? C17A C13 C12 C11 172.8(3) . . . . ? C14 C13 C12 C11 56.6(4) . . . . ? C2 C1 C10 C5 -1.7(4) . . . . ? C2 C1 C10 C9 -177.8(3) . . . . ? C4 C5 C10 C1 2.1(4) . . . . ? C6 C5 C10 C1 -176.5(3) . . . . ? C4 C5 C10 C9 178.3(3) . . . . ? C6 C5 C10 C9 -0.3(5) . . . . ? C10 C5 C4 C3 -0.6(5) . . . . ? C6 C5 C4 C3 178.0(3) . . . . ? O1 C20 C21 C22 142.6(3) . . . . ? O1 C20 C21 C26 -39.2(4) . . . . ? C20 O1 C3 C4 -174.8(3) . . . . ? C20 O1 C3 C2 4.7(4) . . . . ? C5 C4 C3 O1 178.1(3) . . . . ? C5 C4 C3 C2 -1.4(5) . . . . ? C1 C2 C3 O1 -177.7(3) . . . . ? C1 C2 C3 C4 1.8(4) . . . . ? C13 C12 C11 C9 -57.3(4) . . . . ? C1 C10 C9 C8 141.7(3) . . . . ? C5 C10 C9 C8 -34.3(4) . . . . ? C1 C10 C9 C11 15.6(4) . . . . ? C5 C10 C9 C11 -160.4(3) . . . . ? C12 C11 C9 C10 176.1(3) . . . . ? C12 C11 C9 C8 51.2(4) . . . . ? C10 C9 C8 C14 -175.7(2) . . . . ? C11 C9 C8 C14 -48.8(3) . . . . ? C10 C9 C8 C7 60.1(3) . . . . ? C11 C9 C8 C7 -172.9(3) . . . . ? C15 C14 C8 C9 177.4(3) . . . . ? C13 C14 C8 C9 51.6(3) . . . . ? C15 C14 C8 C7 -60.5(4) . . . . ? C13 C14 C8 C7 173.6(3) . . . . ? N3 N4 C16 N1 -0.1(4) . . . . ? N3 N4 C16 C15 179.2(4) . . . . ? N2 N1 C16 N4 0.8(4) . . . . ? C17A N1 C16 N4 178.8(3) . . . . ? N2 N1 C16 C15 -178.5(4) . . . . ? C17A N1 C16 C15 -0.5(6) . . . . ? C16 N1 C17A C19 148.6(4) . . . . ? N2 N1 C17A C19 -33.7(5) . . . . ? C16 N1 C17A C13 20.8(5) . . . . ? N2 N1 C17A C13 -161.5(3) . . . . ? C12 C13 C17A N1 -166.0(3) . . . . ? C18 C13 C17A N1 72.5(3) . . . . ? C14 C13 C17A N1 -50.3(3) . . . . ? C12 C13 C17A C19 69.9(4) . . . . ? C18 C13 C17A C19 -51.7(4) . . . . ? C14 C13 C17A C19 -174.4(4) . . . . ? C26 C21 C22 C23 -0.8(5) . . . . ? C20 C21 C22 C23 177.4(3) . . . . ? C22 C21 C26 C25 0.2(5) . . . . ? C20 C21 C26 C25 -178.0(3) . . . . ? C21 C22 C23 C24 0.8(5) . . . . ? C4 C5 C6 C7 -171.4(3) . . . . ? C10 C5 C6 C7 7.1(6) . . . . ? C16 N1 N2 N3 -1.2(4) . . . . ? C17A N1 N2 N3 -179.2(3) . . . . ? C5 C6 C7 C8 21.7(5) . . . . ? C9 C8 C7 C6 -55.5(4) . . . . ? C14 C8 C7 C6 179.8(3) . . . . ? N4 C16 C15 C14 -167.2(4) . . . . ? N1 C16 C15 C14 12.0(6) . . . . ? C8 C14 C15 C16 -171.2(3) . . . . ? C13 C14 C15 C16 -43.8(4) . . . . ? N1 N2 N3 N4 1.1(4) . . . . ? C16 N4 N3 N2 -0.6(4) . . . . ? C22 C23 C24 C25 -0.1(6) . . . . ? C23 C24 C25 C26 -0.4(6) . . . . ? C21 C26 C25 C24 0.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.174 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.031