# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_cu_dm13180_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H37 N O2' _chemical_formula_weight 383.56 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.8655(2) _cell_length_b 6.34770(10) _cell_length_c 14.6161(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.0310(10) _cell_angle_gamma 90.00 _cell_volume 1092.59(3) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 4579 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 68.67 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9159 _exptl_absorpt_correction_T_max 0.9780 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7829 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 67.98 _reflns_number_total 3165 _reflns_number_gt 3050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1074P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 3165 _refine_ls_number_parameters 259 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.004 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 0.29554(10) 0.3414(3) 0.45674(9) 0.0271(3) Uani 1 1 d . . . H1 H 0.3655 0.3060 0.4493 0.033 Uiso 1 1 calc R . . O1 O 0.07699(11) 0.8575(3) 0.59106(10) 0.0438(4) Uani 1 1 d . . . O2 O 0.47907(9) 0.5511(3) 0.53457(9) 0.0383(4) Uani 1 1 d . . . C1 C 0.08456(14) 1.0520(4) 0.79243(13) 0.0387(5) Uani 1 1 d . . . H1A H 0.0648 1.1745 0.8292 0.046 Uiso 1 1 calc R . . H1B H 0.0700 1.0897 0.7263 0.046 Uiso 1 1 calc R . . C2 C 0.01353(13) 0.8635(5) 0.81223(15) 0.0501(7) Uani 1 1 d . . . H2A H -0.0665 0.9082 0.8113 0.060 Uiso 1 1 calc R . . H2B H 0.0166 0.7575 0.7629 0.060 Uiso 1 1 calc R . . C3 C 0.05273(16) 0.7645(4) 0.90310(15) 0.0446(6) Uani 1 1 d . . . H3 H 0.0050 0.6616 0.9256 0.054 Uiso 1 1 calc R . . C4 C 0.15025(15) 0.8103(3) 0.95509(13) 0.0343(4) Uani 1 1 d . . . C5 C 0.23461(13) 0.9698(3) 0.92464(11) 0.0240(4) Uani 1 1 d . . . C6 C 0.35673(13) 0.8886(3) 0.94770(12) 0.0300(4) Uani 1 1 d . . . H6A H 0.3763 0.8840 1.0155 0.036 Uiso 1 1 calc R . . H6B H 0.3616 0.7433 0.9239 0.036 Uiso 1 1 calc R . . C7 C 0.44202(13) 1.0270(4) 0.90637(13) 0.0364(5) Uani 1 1 d . . . H7A H 0.5189 0.9670 0.9222 0.044 Uiso 1 1 calc R . . H7B H 0.4416 1.1690 0.9344 0.044 Uiso 1 1 calc R . . C8 C 0.41757(14) 1.0480(4) 0.80168(13) 0.0332(4) Uani 1 1 d . . . H8 H 0.4231 0.9037 0.7752 0.040 Uiso 1 1 calc R . . C9 C 0.29502(15) 1.1293(3) 0.77070(12) 0.0290(4) Uani 1 1 d . . . C10 C 0.21003(13) 0.9946(3) 0.81788(11) 0.0243(4) Uani 1 1 d . . . H10 H 0.2174 0.8492 0.7930 0.029 Uiso 1 1 calc R . . C11 C 0.1777(2) 0.7080(4) 1.04817(15) 0.0499(6) Uani 1 1 d . . . H11A H 0.1176 0.6075 1.0581 0.075 Uiso 1 1 calc R . . H11B H 0.1828 0.8164 1.0963 0.075 Uiso 1 1 calc R . . H11C H 0.2504 0.6337 1.0507 0.075 Uiso 1 1 calc R . . C12 C 0.22158(15) 1.1732(3) 0.98048(12) 0.0316(4) Uani 1 1 d . . . H12A H 0.1503 1.2434 0.9571 0.047 Uiso 1 1 calc R . . H12B H 0.2855 1.2677 0.9742 0.047 Uiso 1 1 calc R . . H12C H 0.2207 1.1375 1.0456 0.047 Uiso 1 1 calc R . . C13 C 0.5113(2) 1.1809(5) 0.76753(18) 0.0566(7) Uani 1 1 d . . . H13A H 0.5174 1.3155 0.8006 0.085 Uiso 1 1 calc R . . H13B H 0.4929 1.2072 0.7013 0.085 Uiso 1 1 calc R . . H13C H 0.5837 1.1054 0.7787 0.085 Uiso 1 1 calc R . . C14 C 0.2837(2) 1.3666(4) 0.78857(15) 0.0476(6) Uani 1 1 d . . . H14A H 0.2031 1.4047 0.7835 0.071 Uiso 1 1 calc R . . H14B H 0.3205 1.4461 0.7430 0.071 Uiso 1 1 calc R . . H14C H 0.3203 1.4004 0.8506 0.071 Uiso 1 1 calc R . . C15 C 0.26879(17) 1.1072(3) 0.66314(13) 0.0356(4) Uani 1 1 d . . . H15A H 0.1907 1.1602 0.6454 0.043 Uiso 1 1 calc R . . H15B H 0.3206 1.2042 0.6355 0.043 Uiso 1 1 calc R . . C16 C 0.27695(14) 0.8965(3) 0.61754(11) 0.0280(4) Uani 1 1 d . . . C17 C 0.16942(13) 0.7808(3) 0.57895(12) 0.0290(4) Uani 1 1 d . . . C18 C 0.17755(13) 0.5898(3) 0.52675(11) 0.0268(4) Uani 1 1 d . . . H18 H 0.1099 0.5165 0.5045 0.032 Uiso 1 1 calc R . . C19 C 0.27927(13) 0.5113(3) 0.50839(11) 0.0247(4) Uani 1 1 d . . . C20 C 0.38635(13) 0.6214(3) 0.54804(11) 0.0268(4) Uani 1 1 d . . . C21 C 0.37676(13) 0.8138(3) 0.60012(11) 0.0287(4) Uani 1 1 d . . . H21 H 0.4446 0.8855 0.6232 0.034 Uiso 1 1 calc R . . C22 C 0.20286(14) 0.2133(3) 0.41266(12) 0.0297(4) Uani 1 1 d . . . H22A H 0.1480 0.3044 0.3745 0.036 Uiso 1 1 calc R . . H22B H 0.1627 0.1460 0.4605 0.036 Uiso 1 1 calc R . . C23 C 0.24644(16) 0.0438(4) 0.35212(13) 0.0362(4) Uani 1 1 d . . . H23 H 0.3054 -0.0404 0.3910 0.043 Uiso 1 1 calc R . . C24 C 0.1499(2) -0.1044(4) 0.31590(16) 0.0504(6) Uani 1 1 d . . . H24A H 0.0959 -0.0294 0.2712 0.076 Uiso 1 1 calc R . . H24B H 0.1110 -0.1533 0.3673 0.076 Uiso 1 1 calc R . . H24C H 0.1809 -0.2257 0.2858 0.076 Uiso 1 1 calc R . . C25 C 0.30119(16) 0.1394(4) 0.27301(14) 0.0449(6) Uani 1 1 d . . . H25A H 0.2462 0.2302 0.2363 0.067 Uiso 1 1 calc R . . H25B H 0.3253 0.0265 0.2340 0.067 Uiso 1 1 calc R . . H25C H 0.3674 0.2231 0.2978 0.067 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 0.0203(6) 0.0304(9) 0.0304(6) -0.0049(7) 0.0019(5) 0.0017(6) O1 0.0323(6) 0.0511(10) 0.0472(7) -0.0129(7) 0.0012(5) 0.0152(7) O2 0.0220(5) 0.0474(10) 0.0462(7) -0.0155(7) 0.0070(5) -0.0029(6) C1 0.0299(8) 0.0492(13) 0.0360(9) -0.0105(10) -0.0004(7) 0.0148(9) C2 0.0210(7) 0.0783(19) 0.0514(10) -0.0290(13) 0.0055(7) -0.0059(10) C3 0.0372(9) 0.0508(15) 0.0504(11) -0.0203(11) 0.0239(8) -0.0187(10) C4 0.0412(9) 0.0274(11) 0.0374(9) -0.0097(9) 0.0181(7) -0.0056(8) C5 0.0241(7) 0.0215(9) 0.0265(7) -0.0034(7) 0.0039(6) 0.0007(6) C6 0.0282(7) 0.0309(11) 0.0300(7) -0.0021(8) -0.0006(6) 0.0035(8) C7 0.0226(7) 0.0462(13) 0.0395(9) -0.0126(9) 0.0005(6) -0.0051(8) C8 0.0273(7) 0.0352(11) 0.0384(9) -0.0109(9) 0.0097(7) -0.0125(8) C9 0.0395(9) 0.0176(9) 0.0305(8) -0.0019(7) 0.0063(7) -0.0041(7) C10 0.0240(7) 0.0193(9) 0.0292(8) -0.0032(7) 0.0014(6) 0.0025(6) C11 0.0800(14) 0.0344(12) 0.0399(10) 0.0002(10) 0.0255(10) -0.0099(12) C12 0.0356(8) 0.0260(11) 0.0334(8) -0.0080(8) 0.0055(7) -0.0009(7) C13 0.0523(11) 0.0632(18) 0.0583(13) -0.0215(13) 0.0236(10) -0.0351(13) C14 0.0832(15) 0.0216(12) 0.0398(10) -0.0022(9) 0.0141(10) -0.0037(11) C15 0.0520(10) 0.0239(11) 0.0322(9) 0.0042(8) 0.0096(8) 0.0031(9) C16 0.0373(8) 0.0234(10) 0.0233(7) 0.0032(7) 0.0042(6) 0.0008(7) C17 0.0280(7) 0.0323(11) 0.0268(7) 0.0048(8) 0.0038(6) 0.0071(8) C18 0.0229(7) 0.0292(11) 0.0276(7) 0.0008(7) 0.0006(6) 0.0005(7) C19 0.0232(7) 0.0277(10) 0.0231(7) 0.0032(7) 0.0026(5) -0.0008(7) C20 0.0247(7) 0.0315(10) 0.0249(7) 0.0003(7) 0.0065(6) -0.0025(7) C21 0.0285(7) 0.0311(11) 0.0272(7) -0.0029(8) 0.0059(6) -0.0087(8) C22 0.0267(7) 0.0301(10) 0.0312(8) -0.0015(8) -0.0011(6) -0.0020(8) C23 0.0414(9) 0.0296(11) 0.0343(8) -0.0061(9) -0.0086(7) 0.0095(9) C24 0.0676(13) 0.0311(14) 0.0462(11) -0.0051(10) -0.0185(10) -0.0014(11) C25 0.0403(9) 0.0555(15) 0.0385(10) -0.0137(10) 0.0033(8) 0.0162(11) _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 C19 1.344(2) . ? N1 C22 1.453(2) . ? N1 H1 0.8800 . ? O1 C17 1.232(2) . ? O2 C20 1.225(2) . ? C1 C2 1.512(4) . ? C1 C10 1.534(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.491(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.336(3) . ? C3 H3 0.9500 . ? C4 C11 1.507(3) . ? C4 C5 1.528(2) . ? C5 C6 1.536(2) . ? C5 C12 1.545(2) . ? C5 C10 1.560(2) . ? C6 C7 1.520(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.528(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.528(3) . ? C8 C9 1.557(2) . ? C8 H8 1.0000 . ? C9 C14 1.538(3) . ? C9 C10 1.547(2) . ? C9 C15 1.571(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.503(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.348(2) . ? C16 C17 1.519(2) . ? C17 C18 1.442(3) . ? C18 C19 1.362(2) . ? C18 H18 0.9500 . ? C19 C20 1.503(2) . ? C20 C21 1.451(3) . ? C21 H21 0.9500 . ? C22 C23 1.523(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C25 1.520(3) . ? C23 C24 1.526(3) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C19 N1 C22 123.02(13) . . ? C19 N1 H1 118.5 . . ? C22 N1 H1 118.5 . . ? C2 C1 C10 108.23(18) . . ? C2 C1 H1A 110.1 . . ? C10 C1 H1A 110.1 . . ? C2 C1 H1B 110.1 . . ? C10 C1 H1B 110.1 . . ? H1A C1 H1B 108.4 . . ? C3 C2 C1 112.55(16) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 124.7(2) . . ? C4 C3 H3 117.7 . . ? C2 C3 H3 117.7 . . ? C3 C4 C11 119.7(2) . . ? C3 C4 C5 122.08(19) . . ? C11 C4 C5 118.15(17) . . ? C4 C5 C6 110.37(16) . . ? C4 C5 C12 106.76(13) . . ? C6 C5 C12 108.48(14) . . ? C4 C5 C10 108.01(14) . . ? C6 C5 C10 108.01(13) . . ? C12 C5 C10 115.18(14) . . ? C7 C6 C5 112.04(16) . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 113.23(14) . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C13 C8 C7 108.59(16) . . ? C13 C8 C9 114.41(19) . . ? C7 C8 C9 112.10(14) . . ? C13 C8 H8 107.1 . . ? C7 C8 H8 107.1 . . ? C9 C8 H8 107.1 . . ? C14 C9 C10 112.99(15) . . ? C14 C9 C8 111.89(18) . . ? C10 C9 C8 108.89(15) . . ? C14 C9 C15 104.27(16) . . ? C10 C9 C15 109.68(14) . . ? C8 C9 C15 108.97(14) . . ? C1 C10 C9 115.27(15) . . ? C1 C10 C5 108.88(13) . . ? C9 C10 C5 116.70(13) . . ? C1 C10 H10 104.9 . . ? C9 C10 H10 104.9 . . ? C5 C10 H10 104.9 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C9 120.49(16) . . ? C16 C15 H15A 107.2 . . ? C9 C15 H15A 107.2 . . ? C16 C15 H15B 107.2 . . ? C9 C15 H15B 107.2 . . ? H15A C15 H15B 106.8 . . ? C21 C16 C15 122.41(17) . . ? C21 C16 C17 117.33(17) . . ? C15 C16 C17 119.87(16) . . ? O1 C17 C18 121.76(17) . . ? O1 C17 C16 118.51(19) . . ? C18 C17 C16 119.68(14) . . ? C19 C18 C17 121.99(16) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? N1 C19 C18 126.56(16) . . ? N1 C19 C20 114.64(13) . . ? C18 C19 C20 118.80(17) . . ? O2 C20 C21 121.36(16) . . ? O2 C20 C19 120.15(17) . . ? C21 C20 C19 118.48(14) . . ? C16 C21 C20 123.64(16) . . ? C16 C21 H21 118.2 . . ? C20 C21 H21 118.2 . . ? N1 C22 C23 111.12(14) . . ? N1 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? N1 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C25 C23 C22 111.53(18) . . ? C25 C23 C24 110.78(18) . . ? C22 C23 C24 110.07(16) . . ? C25 C23 H23 108.1 . . ? C22 C23 H23 108.1 . . ? C24 C23 H23 108.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C10 C1 C2 C3 44.7(2) . . . . ? C1 C2 C3 C4 -11.0(3) . . . . ? C2 C3 C4 C11 176.7(2) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C3 C4 C5 C6 -138.51(19) . . . . ? C11 C4 C5 C6 43.4(2) . . . . ? C3 C4 C5 C12 103.8(2) . . . . ? C11 C4 C5 C12 -74.3(2) . . . . ? C3 C4 C5 C10 -20.6(2) . . . . ? C11 C4 C5 C10 161.29(17) . . . . ? C4 C5 C6 C7 171.74(14) . . . . ? C12 C5 C6 C7 -71.61(18) . . . . ? C10 C5 C6 C7 53.87(19) . . . . ? C5 C6 C7 C8 -57.7(2) . . . . ? C6 C7 C8 C13 -177.33(18) . . . . ? C6 C7 C8 C9 55.3(2) . . . . ? C13 C8 C9 C14 -48.7(2) . . . . ? C7 C8 C9 C14 75.5(2) . . . . ? C13 C8 C9 C10 -174.32(16) . . . . ? C7 C8 C9 C10 -50.1(2) . . . . ? C13 C8 C9 C15 66.1(2) . . . . ? C7 C8 C9 C15 -169.70(17) . . . . ? C2 C1 C10 C9 158.33(15) . . . . ? C2 C1 C10 C5 -68.31(19) . . . . ? C14 C9 C10 C1 56.4(2) . . . . ? C8 C9 C10 C1 -178.62(15) . . . . ? C15 C9 C10 C1 -59.5(2) . . . . ? C14 C9 C10 C5 -73.2(2) . . . . ? C8 C9 C10 C5 51.7(2) . . . . ? C15 C9 C10 C5 170.89(15) . . . . ? C4 C5 C10 C1 54.5(2) . . . . ? C6 C5 C10 C1 173.83(16) . . . . ? C12 C5 C10 C1 -64.8(2) . . . . ? C4 C5 C10 C9 -172.93(14) . . . . ? C6 C5 C10 C9 -53.6(2) . . . . ? C12 C5 C10 C9 67.86(18) . . . . ? C14 C9 C15 C16 177.00(18) . . . . ? C10 C9 C15 C16 -61.7(2) . . . . ? C8 C9 C15 C16 57.4(2) . . . . ? C9 C15 C16 C21 -80.6(2) . . . . ? C9 C15 C16 C17 106.8(2) . . . . ? C21 C16 C17 O1 -177.36(17) . . . . ? C15 C16 C17 O1 -4.4(2) . . . . ? C21 C16 C17 C18 0.5(2) . . . . ? C15 C16 C17 C18 173.45(15) . . . . ? O1 C17 C18 C19 175.92(18) . . . . ? C16 C17 C18 C19 -1.8(2) . . . . ? C22 N1 C19 C18 -0.5(3) . . . . ? C22 N1 C19 C20 179.79(15) . . . . ? C17 C18 C19 N1 -176.41(16) . . . . ? C17 C18 C19 C20 3.2(3) . . . . ? N1 C19 C20 O2 -2.2(2) . . . . ? C18 C19 C20 O2 178.15(17) . . . . ? N1 C19 C20 C21 176.33(14) . . . . ? C18 C19 C20 C21 -3.4(2) . . . . ? C15 C16 C21 C20 -173.53(15) . . . . ? C17 C16 C21 C20 -0.7(3) . . . . ? O2 C20 C21 C16 -179.38(18) . . . . ? C19 C20 C21 C16 2.2(3) . . . . ? C19 N1 C22 C23 175.02(15) . . . . ? N1 C22 C23 C25 -63.4(2) . . . . ? N1 C22 C23 C24 173.26(16) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 67.98 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.178 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 974398' ####################################################################### # # 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_cu_dm13188_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H39 N O2' _chemical_formula_weight 397.58 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 P2(1)2(1)2(1) 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 11.9570(4) _cell_length_b 12.5129(4) _cell_length_c 15.4458(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2310.95(12) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 9961 _cell_measurement_theta_min 3.70 _cell_measurement_theta_max 68.85 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8715 _exptl_absorpt_correction_T_max 0.9180 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15390 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 69.35 _reflns_number_total 4200 _reflns_number_gt 4119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1657P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 4200 _refine_ls_number_parameters 299 _refine_ls_number_restraints 105 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1856 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.072 _refine_ls_shift/su_mean 0.006 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 0.99090(15) 0.28357(15) 1.05337(12) 0.0419(4) Uani 1 1 d . A . H1C H 1.0622 0.2732 1.0647 0.050 Uiso 1 1 calc R . . O1 O 0.70120(13) 0.16738(15) 0.86623(11) 0.0511(4) Uani 1 1 d . . . O2 O 1.11584(14) 0.12601(13) 0.98488(12) 0.0524(4) Uani 1 1 d . . . C1 C 0.71237(16) 0.14980(19) 0.65829(14) 0.0435(5) Uani 1 1 d . . . H1A H 0.6752 0.1150 0.6084 0.052 Uiso 1 1 calc R . . H1B H 0.6766 0.1236 0.7120 0.052 Uiso 1 1 calc R . . C2 C 0.69926(19) 0.2705(2) 0.65180(17) 0.0525(6) Uani 1 1 d . . . H2A H 0.6221 0.2873 0.6329 0.063 Uiso 1 1 calc R . . H2B H 0.7103 0.3023 0.7099 0.063 Uiso 1 1 calc R . . C3 C 0.7798(2) 0.32014(18) 0.59010(15) 0.0494(5) Uani 1 1 d . . . H3A H 0.7687 0.3932 0.5757 0.059 Uiso 1 1 calc R . . C4 C 0.8656(2) 0.27051(17) 0.55388(13) 0.0450(5) Uani 1 1 d . . . C5 C 0.88960(18) 0.15227(16) 0.56968(13) 0.0391(4) Uani 1 1 d . . . C6 C 1.0166(2) 0.1311(2) 0.57415(17) 0.0513(5) Uani 1 1 d . . . H6A H 1.0501 0.1443 0.5165 0.062 Uiso 1 1 calc R . . H6B H 1.0511 0.1815 0.6157 0.062 Uiso 1 1 calc R . . C7 C 1.0420(3) 0.0186(2) 0.60172(17) 0.0604(7) Uani 1 1 d . . . H7A H 1.1241 0.0083 0.6025 0.072 Uiso 1 1 calc R . . H7B H 1.0102 -0.0316 0.5587 0.072 Uiso 1 1 calc R . . C8 C 0.9952(2) -0.00755(18) 0.69033(16) 0.0466(5) Uani 1 1 d . . . H8A H 1.0286 0.0448 0.7318 0.056 Uiso 1 1 calc R . . C9 C 0.86607(18) 0.00779(15) 0.69451(13) 0.0394(5) Uani 1 1 d . . . C10 C 0.83708(15) 0.12142(14) 0.65889(12) 0.0329(4) Uani 1 1 d . . . H10A H 0.8714 0.1721 0.7013 0.039 Uiso 1 1 calc R . . C11 C 0.9431(3) 0.3293(2) 0.49272(17) 0.0635(7) Uani 1 1 d . . . H11A H 0.9195 0.4041 0.4880 0.095 Uiso 1 1 calc R . . H11B H 0.9404 0.2956 0.4355 0.095 Uiso 1 1 calc R . . H11C H 1.0198 0.3262 0.5151 0.095 Uiso 1 1 calc R . . C12 C 0.8410(3) 0.0921(2) 0.49024(15) 0.0598(7) Uani 1 1 d . . . H12A H 0.7602 0.1046 0.4869 0.090 Uiso 1 1 calc R . . H12B H 0.8553 0.0154 0.4964 0.090 Uiso 1 1 calc R . . H12C H 0.8768 0.1184 0.4373 0.090 Uiso 1 1 calc R . . C13 C 1.0341(3) -0.1199(2) 0.71923(19) 0.0653(7) Uani 1 1 d . . . H13A H 1.1157 -0.1244 0.7152 0.098 Uiso 1 1 calc R . . H13B H 1.0003 -0.1741 0.6816 0.098 Uiso 1 1 calc R . . H13C H 1.0109 -0.1325 0.7792 0.098 Uiso 1 1 calc R . . C14 C 0.8044(3) -0.08141(19) 0.64638(17) 0.0608(7) Uani 1 1 d . . . H14A H 0.8263 -0.0807 0.5852 0.091 Uiso 1 1 calc R . . H14B H 0.7236 -0.0701 0.6511 0.091 Uiso 1 1 calc R . . H14C H 0.8240 -0.1506 0.6720 0.091 Uiso 1 1 calc R . . C15 C 0.82554(18) -0.00102(15) 0.79104(14) 0.0413(5) Uani 1 1 d . . . H15A H 0.7433 0.0080 0.7912 0.050 Uiso 1 1 calc R . . H15B H 0.8411 -0.0748 0.8109 0.050 Uiso 1 1 calc R . . C16 C 0.87288(17) 0.07422(14) 0.85772(12) 0.0344(4) Uani 1 1 d . . . C17 C 0.79708(15) 0.16032(16) 0.89393(12) 0.0352(4) Uani 1 1 d . . . C18 C 0.83740(15) 0.22930(15) 0.96104(12) 0.0351(4) Uani 1 1 d . . . H18A H 0.7888 0.2822 0.9842 0.042 Uiso 1 1 calc R . . C19 C 0.94378(15) 0.22121(14) 0.99270(12) 0.0328(4) Uani 1 1 d . . . C20 C 1.01961(16) 0.13595(15) 0.95740(13) 0.0358(4) Uani 1 1 d . . . C21 C 0.97589(17) 0.06514(15) 0.89065(13) 0.0367(4) Uani 1 1 d . . . H21A H 1.0229 0.0098 0.8695 0.044 Uiso 1 1 calc R . . C22 C 0.93389(19) 0.36668(17) 1.10182(15) 0.0440(5) Uani 1 1 d U . . H22A H 0.8838 0.4039 1.0637 0.053 Uiso 1 1 d R A . H22B H 0.9877 0.4173 1.1230 0.053 Uiso 1 1 d R . . C23 C 0.8729(8) 0.3239(7) 1.1764(8) 0.0534(16) Uani 0.70 1 d PU A 1 H23A H 0.8113 0.2827 1.1482 0.064 Uiso 0.70 1 calc PR A 1 C24 C 0.8050(6) 0.4197(8) 1.2251(6) 0.0589(14) Uani 0.70 1 d PU A 1 H24A H 0.7479 0.3901 1.2648 0.071 Uiso 0.70 1 calc PR A 1 H24B H 0.7674 0.4665 1.1823 0.071 Uiso 0.70 1 calc PR A 1 C25 C 0.9031(7) 0.4883(6) 1.2807(4) 0.0627(15) Uani 0.70 1 d PU A 1 H25A H 0.8666 0.5420 1.3173 0.094 Uiso 0.70 1 calc PR A 1 H25B H 0.9536 0.5240 1.2399 0.094 Uiso 0.70 1 calc PR A 1 H25C H 0.9459 0.4389 1.3170 0.094 Uiso 0.70 1 calc PR A 1 C26 C 0.9205(3) 0.2472(3) 1.2323(2) 0.0534(8) Uani 0.70 1 d PU A 1 H26A H 0.9607 0.1936 1.1980 0.080 Uiso 0.70 1 calc PR A 1 H26B H 0.8611 0.2123 1.2656 0.080 Uiso 0.70 1 calc PR A 1 H26C H 0.9727 0.2825 1.2720 0.080 Uiso 0.70 1 calc PR A 1 C23' C 0.8521(16) 0.3274(19) 1.1735(16) 0.041(2) Uani 0.30 1 d PU A 2 H23B H 0.7806 0.3049 1.1469 0.049 Uiso 0.30 1 calc PR A 2 H23C H 0.8847 0.2649 1.2037 0.049 Uiso 0.30 1 calc PR A 2 C24' C 0.8318(15) 0.4123(18) 1.2352(14) 0.056(3) Uani 0.30 1 d PU A 2 H24C H 0.7700 0.4503 1.2043 0.068 Uiso 0.30 1 calc PR A 2 C25' C 0.8807(14) 0.4846(15) 1.2595(11) 0.058(4) Uani 0.30 1 d PU A 2 H25D H 0.9165 0.5206 1.2104 0.087 Uiso 0.30 1 calc PR A 2 H25E H 0.9380 0.4611 1.3006 0.087 Uiso 0.30 1 calc PR A 2 H25F H 0.8294 0.5343 1.2883 0.087 Uiso 0.30 1 calc PR A 2 C26' C 0.7639(10) 0.3507(13) 1.2993(7) 0.083(3) Uani 0.30 1 d PU A 2 H26D H 0.7318 0.3999 1.3420 0.125 Uiso 0.30 1 calc PR A 2 H26E H 0.8118 0.2987 1.3289 0.125 Uiso 0.30 1 calc PR A 2 H26F H 0.7035 0.3130 1.2692 0.125 Uiso 0.30 1 calc PRU A 2 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 0.0436(8) 0.0466(9) 0.0354(9) -0.0091(8) -0.0051(7) 0.0049(7) O1 0.0312(7) 0.0794(11) 0.0426(9) -0.0123(8) -0.0015(6) -0.0008(7) O2 0.0418(8) 0.0560(8) 0.0592(10) -0.0171(8) -0.0138(7) 0.0099(7) C1 0.0332(9) 0.0585(12) 0.0387(10) -0.0037(9) -0.0065(8) -0.0049(8) C2 0.0418(10) 0.0644(14) 0.0513(13) -0.0051(11) -0.0068(9) 0.0121(10) C3 0.0636(13) 0.0457(11) 0.0389(11) 0.0008(8) -0.0115(10) 0.0083(9) C4 0.0652(13) 0.0413(10) 0.0286(9) -0.0026(8) -0.0025(9) 0.0012(9) C5 0.0510(10) 0.0397(9) 0.0266(9) -0.0046(7) 0.0010(8) 0.0001(8) C6 0.0535(12) 0.0637(13) 0.0368(11) 0.0031(10) 0.0146(9) 0.0061(10) C7 0.0728(16) 0.0684(15) 0.0400(12) -0.0052(11) 0.0134(12) 0.0297(13) C8 0.0578(12) 0.0463(11) 0.0359(11) -0.0018(9) 0.0014(9) 0.0166(9) C9 0.0523(11) 0.0350(9) 0.0309(10) -0.0037(7) -0.0021(8) -0.0045(7) C10 0.0360(9) 0.0341(8) 0.0286(9) -0.0059(7) -0.0046(7) -0.0057(7) C11 0.097(2) 0.0519(13) 0.0418(12) 0.0042(10) 0.0123(14) -0.0020(13) C12 0.0963(19) 0.0532(12) 0.0298(10) -0.0104(10) -0.0096(12) 0.0009(12) C13 0.097(2) 0.0537(14) 0.0457(12) -0.0042(11) -0.0018(14) 0.0328(13) C14 0.099(2) 0.0395(10) 0.0438(12) -0.0081(10) -0.0121(13) -0.0176(11) C15 0.0516(11) 0.0381(9) 0.0342(10) -0.0043(7) -0.0048(8) -0.0107(8) C16 0.0405(9) 0.0340(8) 0.0286(9) -0.0012(7) 0.0044(7) -0.0071(7) C17 0.0332(8) 0.0450(10) 0.0273(8) 0.0019(8) 0.0052(7) -0.0054(7) C18 0.0338(8) 0.0418(9) 0.0296(9) -0.0007(7) 0.0051(7) -0.0004(7) C19 0.0365(9) 0.0346(8) 0.0272(8) 0.0001(7) 0.0022(7) -0.0017(7) C20 0.0343(9) 0.0385(9) 0.0344(10) -0.0028(7) -0.0007(7) 0.0000(7) C21 0.0442(9) 0.0350(9) 0.0307(9) -0.0064(7) -0.0011(8) 0.0012(7) C22 0.0562(11) 0.0419(10) 0.0338(9) -0.0063(8) -0.0049(9) 0.0046(8) C23 0.076(5) 0.042(2) 0.043(2) 0.0031(17) 0.004(3) -0.012(3) C24 0.059(3) 0.066(2) 0.051(3) 0.004(2) 0.006(2) 0.006(2) C25 0.092(4) 0.056(2) 0.040(3) 0.0031(19) 0.001(2) 0.013(3) C26 0.0645(19) 0.0485(17) 0.0472(18) 0.0103(13) -0.0102(16) 0.0024(14) C23' 0.038(4) 0.055(4) 0.031(4) 0.008(3) -0.008(3) 0.015(3) C24' 0.063(6) 0.063(4) 0.044(4) -0.005(4) 0.001(4) 0.020(4) C25' 0.059(5) 0.052(4) 0.063(6) 0.009(4) -0.009(4) 0.011(3) C26' 0.064(5) 0.126(8) 0.059(5) -0.036(5) -0.002(4) -0.013(5) _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 C19 1.343(3) . ? N1 C22 1.451(3) . ? N1 H1C 0.8800 . ? O1 C17 1.227(3) . ? O2 C20 1.233(3) . ? C1 C2 1.522(3) . ? C1 C10 1.533(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.491(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.323(4) . ? C3 H3A 0.9500 . ? C4 C11 1.514(3) . ? C4 C5 1.527(3) . ? C5 C6 1.543(3) . ? C5 C12 1.552(3) . ? C5 C10 1.563(3) . ? C6 C7 1.501(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.515(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.547(3) . ? C8 C9 1.557(3) . ? C8 H8A 1.0000 . ? C9 C14 1.530(3) . ? C9 C10 1.563(3) . ? C9 C15 1.572(3) . ? C10 H10A 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.506(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.338(3) . ? C16 C17 1.515(3) . ? C17 C18 1.432(3) . ? C18 C19 1.366(3) . ? C18 H18A 0.9500 . ? C19 C20 1.502(3) . ? C20 C21 1.456(3) . ? C21 H21A 0.9500 . ? C22 C23 1.464(11) . ? C22 C23' 1.56(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C23 C26 1.410(10) . ? C23 C24 1.632(16) . ? C23 H23A 1.0000 . ? C24 C25 1.688(12) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C23' C24' 1.45(4) . ? C23' H23B 0.9900 . ? C23' H23C 0.9900 . ? C24' C25' 1.14(3) . ? C24' C26' 1.50(3) . ? C24' H24C 1.0000 . ? C25' H25D 0.9800 . ? C25' H25E 0.9800 . ? C25' H25F 0.9800 . ? C26' H26D 0.9800 . ? C26' H26E 0.9800 . ? C26' H26F 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 C19 N1 C22 125.38(17) . . ? C19 N1 H1C 117.3 . . ? C22 N1 H1C 117.3 . . ? C2 C1 C10 109.30(17) . . ? C2 C1 H1A 109.8 . . ? C10 C1 H1A 109.8 . . ? C2 C1 H1B 109.8 . . ? C10 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? C3 C2 C1 112.9(2) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 125.1(2) . . ? C4 C3 H3A 117.4 . . ? C2 C3 H3A 117.4 . . ? C3 C4 C11 120.7(2) . . ? C3 C4 C5 122.2(2) . . ? C11 C4 C5 117.1(2) . . ? C4 C5 C6 111.04(19) . . ? C4 C5 C12 105.84(18) . . ? C6 C5 C12 108.7(2) . . ? C4 C5 C10 107.74(16) . . ? C6 C5 C10 108.26(17) . . ? C12 C5 C10 115.27(18) . . ? C7 C6 C5 111.9(2) . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 112.59(19) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C13 110.24(19) . . ? C7 C8 C9 112.2(2) . . ? C13 C8 C9 113.5(2) . . ? C7 C8 H8A 106.8 . . ? C13 C8 H8A 106.8 . . ? C9 C8 H8A 106.8 . . ? C14 C9 C8 111.6(2) . . ? C14 C9 C10 112.68(18) . . ? C8 C9 C10 108.50(16) . . ? C14 C9 C15 105.14(17) . . ? C8 C9 C15 109.66(18) . . ? C10 C9 C15 109.22(16) . . ? C1 C10 C9 115.37(16) . . ? C1 C10 C5 109.16(16) . . ? C9 C10 C5 116.48(15) . . ? C1 C10 H10A 104.8 . . ? C9 C10 H10A 104.8 . . ? C5 C10 H10A 104.8 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C9 119.28(16) . . ? C16 C15 H15A 107.5 . . ? C9 C15 H15A 107.5 . . ? C16 C15 H15B 107.5 . . ? C9 C15 H15B 107.5 . . ? H15A C15 H15B 107.0 . . ? C21 C16 C15 123.59(17) . . ? C21 C16 C17 118.09(16) . . ? C15 C16 C17 118.18(17) . . ? O1 C17 C18 121.56(18) . . ? O1 C17 C16 118.78(18) . . ? C18 C17 C16 119.63(17) . . ? C19 C18 C17 121.84(17) . . ? C19 C18 H18A 119.1 . . ? C17 C18 H18A 119.1 . . ? N1 C19 C18 126.66(17) . . ? N1 C19 C20 114.36(17) . . ? C18 C19 C20 118.98(17) . . ? O2 C20 C21 121.15(17) . . ? O2 C20 C19 120.67(18) . . ? C21 C20 C19 118.18(16) . . ? C16 C21 C20 123.24(17) . . ? C16 C21 H21A 118.4 . . ? C20 C21 H21A 118.4 . . ? N1 C22 C23 112.2(4) . . ? N1 C22 C23' 115.8(9) . . ? C23 C22 C23' 9.1(9) . . ? N1 C22 H22A 108.9 . . ? C23 C22 H22A 110.4 . . ? C23' C22 H22A 101.4 . . ? N1 C22 H22B 109.5 . . ? C23 C22 H22B 107.8 . . ? C23' C22 H22B 112.7 . . ? H22A C22 H22B 107.9 . . ? C26 C23 C22 122.0(7) . . ? C26 C23 C24 114.8(9) . . ? C22 C23 C24 110.0(7) . . ? C26 C23 H23A 102.3 . . ? C22 C23 H23A 102.3 . . ? C24 C23 H23A 102.3 . . ? C23 C24 C25 105.2(6) . . ? C23 C24 H24A 110.7 . . ? C25 C24 H24A 110.7 . . ? C23 C24 H24B 110.7 . . ? C25 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.4 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24' C23' C22 109.9(19) . . ? C24' C23' H23B 109.6 . . ? C22 C23' H23B 109.7 . . ? C24' C23' H23C 109.6 . . ? C22 C23' H23C 109.7 . . ? H23B C23' H23C 108.2 . . ? C25' C24' C23' 136(2) . . ? C25' C24' C26' 118.0(19) . . ? C23' C24' C26' 98.5(19) . . ? C25' C24' H24C 99.1 . . ? C23' C24' H24C 99.2 . . ? C26' C24' H24C 99.2 . . ? C24' C25' H25D 109.6 . . ? C24' C25' H25E 109.4 . . ? H25D C25' H25E 109.5 . . ? C24' C25' H25F 109.4 . . ? H25D C25' H25F 109.5 . . ? H25E C25' H25F 109.5 . . ? C24' C26' H26D 109.5 . . ? C24' C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? C24' C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 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 C10 C1 C2 C3 40.9(3) . . . . ? C1 C2 C3 C4 -9.9(3) . . . . ? C2 C3 C4 C11 -179.3(2) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C3 C4 C5 C6 -143.3(2) . . . . ? C11 C4 C5 C6 38.0(3) . . . . ? C3 C4 C5 C12 98.9(3) . . . . ? C11 C4 C5 C12 -79.7(3) . . . . ? C3 C4 C5 C10 -24.9(3) . . . . ? C11 C4 C5 C10 156.4(2) . . . . ? C4 C5 C6 C7 172.13(18) . . . . ? C12 C5 C6 C7 -71.8(3) . . . . ? C10 C5 C6 C7 54.0(2) . . . . ? C5 C6 C7 C8 -59.9(3) . . . . ? C6 C7 C8 C13 -174.2(2) . . . . ? C6 C7 C8 C9 58.3(3) . . . . ? C7 C8 C9 C14 73.7(2) . . . . ? C13 C8 C9 C14 -52.1(3) . . . . ? C7 C8 C9 C10 -51.0(2) . . . . ? C13 C8 C9 C10 -176.79(17) . . . . ? C7 C8 C9 C15 -170.25(19) . . . . ? C13 C8 C9 C15 64.0(2) . . . . ? C2 C1 C10 C9 161.14(17) . . . . ? C2 C1 C10 C5 -65.5(2) . . . . ? C14 C9 C10 C1 55.9(2) . . . . ? C8 C9 C10 C1 179.92(17) . . . . ? C15 C9 C10 C1 -60.6(2) . . . . ? C14 C9 C10 C5 -74.1(2) . . . . ? C8 C9 C10 C5 50.0(2) . . . . ? C15 C9 C10 C5 169.47(15) . . . . ? C4 C5 C10 C1 55.6(2) . . . . ? C6 C5 C10 C1 175.75(17) . . . . ? C12 C5 C10 C1 -62.3(2) . . . . ? C4 C5 C10 C9 -171.58(17) . . . . ? C6 C5 C10 C9 -51.4(2) . . . . ? C12 C5 C10 C9 70.5(2) . . . . ? C14 C9 C15 C16 178.3(2) . . . . ? C8 C9 C15 C16 58.3(2) . . . . ? C10 C9 C15 C16 -60.5(2) . . . . ? C9 C15 C16 C21 -75.0(3) . . . . ? C9 C15 C16 C17 109.3(2) . . . . ? C21 C16 C17 O1 -177.73(18) . . . . ? C15 C16 C17 O1 -1.8(3) . . . . ? C21 C16 C17 C18 0.5(3) . . . . ? C15 C16 C17 C18 176.41(17) . . . . ? O1 C17 C18 C19 179.40(19) . . . . ? C16 C17 C18 C19 1.2(3) . . . . ? C22 N1 C19 C18 5.2(3) . . . . ? C22 N1 C19 C20 -175.58(18) . . . . ? C17 C18 C19 N1 177.85(18) . . . . ? C17 C18 C19 C20 -1.4(3) . . . . ? N1 C19 C20 O2 1.1(3) . . . . ? C18 C19 C20 O2 -179.57(19) . . . . ? N1 C19 C20 C21 -179.42(17) . . . . ? C18 C19 C20 C21 -0.1(3) . . . . ? C15 C16 C21 C20 -177.71(18) . . . . ? C17 C16 C21 C20 -2.0(3) . . . . ? O2 C20 C21 C16 -178.7(2) . . . . ? C19 C20 C21 C16 1.9(3) . . . . ? C19 N1 C22 C23 83.1(5) . . . . ? C19 N1 C22 C23' 74.0(8) . . . . ? N1 C22 C23 C26 44.4(9) . . . . ? C23' C22 C23 C26 160(9) . . . . ? N1 C22 C23 C24 -176.8(5) . . . . ? C23' C22 C23 C24 -62(8) . . . . ? C26 C23 C24 C25 66.1(9) . . . . ? C22 C23 C24 C25 -75.9(8) . . . . ? N1 C22 C23' C24' 160.1(10) . . . . ? C23 C22 C23' C24' 92(9) . . . . ? C22 C23' C24' C25' -28(3) . . . . ? C22 C23' C24' C26' -174.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 69.35 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.643 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 974399' ####################################################################### # # 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_451 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 N O2' _chemical_formula_sum 'C22 H31 N O2' _chemical_formula_weight 341.48 _chemical_absolute_configuration ad 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' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 7.2191(14) _cell_length_b 7.6075(15) _cell_length_c 35.255(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1936.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1849 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 60.77 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6268 _exptl_absorpt_correction_T_max 0.7529 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8896 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 66.99 _reflns_number_total 3361 _reflns_number_gt 2708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0665P)^2^+0.1415P] 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 SHELXL _refine_ls_extinction_coef 0.0038(5) _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 0.0(4) _refine_ls_number_reflns 3361 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.6884(2) 0.1206(2) 0.20668(6) 0.0650(5) Uani 1 1 d . . . O2 O 0.3665(3) 0.7425(2) 0.20187(6) 0.0717(5) Uani 1 1 d . . . N1 N 0.3237(3) 0.1262(3) 0.21823(6) 0.0574(5) Uani 1 1 d . . . H1A H 0.3913 0.0338 0.2207 0.069 Uiso 1 1 calc R . . C1 C 1.0404(4) 0.5638(4) 0.11990(8) 0.0635(7) Uani 1 1 d . . . H1B H 1.0526 0.5893 0.1467 0.076 Uiso 1 1 calc R . . H1C H 1.1179 0.6458 0.1060 0.076 Uiso 1 1 calc R . . C2 C 1.1056(5) 0.3758(5) 0.11214(9) 0.0772(8) Uani 1 1 d . . . H2A H 1.2399 0.3735 0.1117 0.093 Uiso 1 1 calc R . . H2B H 1.0645 0.3001 0.1326 0.093 Uiso 1 1 calc R . . C3 C 1.0337(4) 0.3064(4) 0.07555(10) 0.0763(9) Uani 1 1 d . . . H3A H 1.0824 0.2003 0.0671 0.092 Uiso 1 1 calc R . . C4 C 0.9069(4) 0.3820(5) 0.05406(8) 0.0735(8) Uani 1 1 d . . . C5 C 0.8254(4) 0.5630(4) 0.06403(8) 0.0663(7) Uani 1 1 d . . . C6 C 0.6193(4) 0.5717(5) 0.05337(8) 0.0765(8) Uani 1 1 d . . . H6A H 0.6068 0.5624 0.0261 0.092 Uiso 1 1 calc R . . H6B H 0.5549 0.4730 0.0647 0.092 Uiso 1 1 calc R . . C7 C 0.5310(4) 0.7410(5) 0.06662(8) 0.0787(8) Uani 1 1 d . . . H7A H 0.4023 0.7423 0.0587 0.094 Uiso 1 1 calc R . . H7B H 0.5927 0.8390 0.0544 0.094 Uiso 1 1 calc R . . C8 C 0.5401(4) 0.7663(4) 0.10957(7) 0.0627(7) Uani 1 1 d . . . H8A H 0.4689 0.6701 0.1209 0.075 Uiso 1 1 calc R . . C9 C 0.7416(3) 0.7510(3) 0.12526(7) 0.0560(6) Uani 1 1 d . . . C10 C 0.8394(3) 0.5875(4) 0.10792(7) 0.0547(6) Uani 1 1 d . . . H10A H 0.7740 0.4862 0.1187 0.066 Uiso 1 1 calc R . . C11 C 0.7299(4) 0.7306(3) 0.16966(7) 0.0579(6) Uani 1 1 d . . . H11A H 0.8554 0.7279 0.1795 0.069 Uiso 1 1 calc R . . H11B H 0.6709 0.8351 0.1798 0.069 Uiso 1 1 calc R . . C12 C 0.6287(3) 0.5730(3) 0.18497(7) 0.0517(6) Uani 1 1 d . . . C13 C 0.7092(3) 0.4164(3) 0.18891(7) 0.0539(6) Uani 1 1 d . . . H13A H 0.8341 0.4059 0.1828 0.065 Uiso 1 1 calc R . . C14 C 0.6114(3) 0.2610(3) 0.20233(6) 0.0503(5) Uani 1 1 d . . . C15 C 0.4072(3) 0.2782(3) 0.20990(6) 0.0481(5) Uani 1 1 d . . . C16 C 0.3286(3) 0.4398(3) 0.20873(7) 0.0547(6) Uani 1 1 d . . . H16A H 0.2035 0.4511 0.2145 0.066 Uiso 1 1 calc R . . C17 C 0.4323(3) 0.5947(3) 0.19880(7) 0.0529(6) Uani 1 1 d . . . C18 C 0.1261(4) 0.1089(4) 0.22333(9) 0.0688(8) Uani 1 1 d . . . H18A H 0.0965 -0.0111 0.2292 0.103 Uiso 1 1 calc R . . H18B H 0.0638 0.1431 0.2004 0.103 Uiso 1 1 calc R . . H18C H 0.0866 0.1833 0.2438 0.103 Uiso 1 1 calc R . . C19 C 0.8425(6) 0.2946(7) 0.01789(11) 0.1197(16) Uani 1 1 d . . . H19A H 0.9047 0.1840 0.0149 0.180 Uiso 1 1 calc R . . H19B H 0.8706 0.3690 -0.0033 0.180 Uiso 1 1 calc R . . H19C H 0.7112 0.2754 0.0191 0.180 Uiso 1 1 calc R . . C20 C 0.9333(5) 0.6990(5) 0.04002(9) 0.0908(11) Uani 1 1 d . . . H20A H 0.9168 0.6735 0.0136 0.136 Uiso 1 1 calc R . . H20B H 1.0626 0.6930 0.0462 0.136 Uiso 1 1 calc R . . H20C H 0.8876 0.8149 0.0454 0.136 Uiso 1 1 calc R . . C21 C 0.4411(4) 0.9368(4) 0.12024(10) 0.0806(9) Uani 1 1 d . . . H21A H 0.3182 0.9361 0.1098 0.121 Uiso 1 1 calc R . . H21B H 0.5087 1.0351 0.1103 0.121 Uiso 1 1 calc R . . H21C H 0.4341 0.9462 0.1474 0.121 Uiso 1 1 calc R . . C22 C 0.8500(4) 0.9212(4) 0.11888(9) 0.0736(8) Uani 1 1 d . . . H22A H 0.9735 0.9078 0.1286 0.110 Uiso 1 1 calc R . . H22B H 0.7894 1.0160 0.1319 0.110 Uiso 1 1 calc R . . H22C H 0.8551 0.9465 0.0922 0.110 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 0.0500(10) 0.0549(10) 0.0900(13) 0.0066(9) 0.0028(9) 0.0096(8) O2 0.0678(12) 0.0525(10) 0.0950(13) 0.0056(10) 0.0159(10) 0.0089(10) N1 0.0427(11) 0.0523(12) 0.0773(14) 0.0060(10) 0.0031(9) -0.0002(9) C1 0.0507(15) 0.0697(17) 0.0702(16) 0.0030(14) -0.0012(12) 0.0012(13) C2 0.0623(17) 0.086(2) 0.0833(19) 0.0053(16) 0.0019(15) 0.0082(17) C3 0.0677(19) 0.075(2) 0.086(2) -0.0052(16) 0.0178(16) 0.0002(16) C4 0.0610(16) 0.092(2) 0.0678(16) -0.0102(16) 0.0133(14) -0.0050(18) C5 0.0523(15) 0.0868(19) 0.0597(14) 0.0074(14) 0.0044(12) -0.0056(14) C6 0.0585(17) 0.111(2) 0.0604(15) -0.0030(16) -0.0050(13) -0.0035(18) C7 0.0570(16) 0.108(2) 0.0710(17) 0.0130(19) -0.0077(13) 0.0038(18) C8 0.0488(14) 0.0699(17) 0.0693(15) 0.0105(14) 0.0005(11) 0.0001(13) C9 0.0477(13) 0.0552(13) 0.0649(14) 0.0074(12) -0.0012(11) -0.0075(12) C10 0.0449(13) 0.0595(14) 0.0598(13) 0.0068(12) 0.0002(10) -0.0074(12) C11 0.0544(14) 0.0534(14) 0.0659(15) -0.0013(12) -0.0020(11) -0.0055(13) C12 0.0471(13) 0.0550(14) 0.0531(12) -0.0027(11) -0.0014(10) -0.0027(12) C13 0.0445(12) 0.0590(15) 0.0581(13) 0.0030(11) 0.0036(10) 0.0005(12) C14 0.0472(12) 0.0508(13) 0.0528(11) -0.0027(11) 0.0004(10) 0.0032(12) C15 0.0439(12) 0.0485(13) 0.0518(11) -0.0001(10) -0.0007(9) 0.0008(11) C16 0.0413(12) 0.0588(14) 0.0639(14) 0.0015(11) 0.0038(10) 0.0037(11) C17 0.0532(14) 0.0463(14) 0.0591(13) 0.0027(11) 0.0026(11) 0.0072(12) C18 0.0455(14) 0.0665(17) 0.095(2) 0.0141(15) 0.0012(13) -0.0039(14) C19 0.100(3) 0.165(4) 0.095(3) -0.056(3) 0.003(2) 0.006(3) C20 0.082(2) 0.119(3) 0.0715(18) 0.0252(19) 0.0162(16) -0.007(2) C21 0.068(2) 0.080(2) 0.094(2) 0.0119(17) -0.0015(16) 0.0092(16) C22 0.0643(18) 0.0657(16) 0.091(2) 0.0152(16) 0.0056(15) -0.0111(15) _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 C14 1.214(3) . ? O2 C17 1.225(3) . ? N1 C15 1.336(3) . ? N1 C18 1.444(3) . ? N1 H1A 0.8600 . ? C1 C10 1.522(4) . ? C1 C2 1.530(4) . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C2 C3 1.487(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.320(4) . ? C3 H3A 0.9300 . ? C4 C19 1.511(4) . ? C4 C5 1.538(5) . ? C5 C6 1.535(4) . ? C5 C20 1.547(4) . ? C5 C10 1.562(4) . ? C6 C7 1.511(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.528(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C21 1.528(4) . ? C8 C9 1.561(3) . ? C8 H8A 0.9800 . ? C9 C22 1.530(4) . ? C9 C10 1.555(4) . ? C9 C11 1.575(3) . ? C10 H10A 0.9800 . ? C11 C12 1.504(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.333(3) . ? C12 C17 1.508(3) . ? C13 C14 1.456(4) . ? C13 H13A 0.9300 . ? C14 C15 1.504(3) . ? C15 C16 1.355(3) . ? C16 C17 1.440(3) . ? C16 H16A 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C15 N1 C18 123.5(2) . . ? C15 N1 H1A 118.3 . . ? C18 N1 H1A 118.3 . . ? C10 C1 C2 110.8(2) . . ? C10 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? C10 C1 H1C 109.5 . . ? C2 C1 H1C 109.5 . . ? H1B C1 H1C 108.1 . . ? C3 C2 C1 112.3(3) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 125.8(3) . . ? C4 C3 H3A 117.1 . . ? C2 C3 H3A 117.1 . . ? C3 C4 C19 120.4(3) . . ? C3 C4 C5 121.6(3) . . ? C19 C4 C5 118.0(3) . . ? C6 C5 C4 110.7(3) . . ? C6 C5 C20 109.0(3) . . ? C4 C5 C20 106.3(2) . . ? C6 C5 C10 107.5(2) . . ? C4 C5 C10 108.0(2) . . ? C20 C5 C10 115.4(2) . . ? C7 C6 C5 111.7(3) . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 113.3(3) . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C21 109.3(2) . . ? C7 C8 C9 112.5(2) . . ? C21 C8 C9 114.4(2) . . ? C7 C8 H8A 106.7 . . ? C21 C8 H8A 106.7 . . ? C9 C8 H8A 106.7 . . ? C22 C9 C10 112.8(2) . . ? C22 C9 C8 111.2(2) . . ? C10 C9 C8 110.1(2) . . ? C22 C9 C11 104.9(2) . . ? C10 C9 C11 109.7(2) . . ? C8 C9 C11 108.1(2) . . ? C1 C10 C9 114.7(2) . . ? C1 C10 C5 108.8(2) . . ? C9 C10 C5 117.1(2) . . ? C1 C10 H10A 105.0 . . ? C9 C10 H10A 105.0 . . ? C5 C10 H10A 105.0 . . ? C12 C11 C9 117.4(2) . . ? C12 C11 H11A 107.9 . . ? C9 C11 H11A 107.9 . . ? C12 C11 H11B 107.9 . . ? C9 C11 H11B 107.9 . . ? H11A C11 H11B 107.2 . . ? C13 C12 C11 122.5(2) . . ? C13 C12 C17 118.3(2) . . ? C11 C12 C17 119.0(2) . . ? C12 C13 C14 123.2(2) . . ? C12 C13 H13A 118.4 . . ? C14 C13 H13A 118.4 . . ? O1 C14 C13 122.2(2) . . ? O1 C14 C15 120.2(2) . . ? C13 C14 C15 117.5(2) . . ? N1 C15 C16 127.1(2) . . ? N1 C15 C14 113.9(2) . . ? C16 C15 C14 119.0(2) . . ? C15 C16 C17 122.2(2) . . ? C15 C16 H16A 118.9 . . ? C17 C16 H16A 118.9 . . ? O2 C17 C16 121.9(2) . . ? O2 C17 C12 119.6(2) . . ? C16 C17 C12 118.5(2) . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C5 C20 H20A 109.5 . . ? C5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 C21 H21A 109.5 . . ? C8 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C8 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C9 C22 H22A 109.5 . . ? C9 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C9 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C10 C1 C2 C3 39.7(3) . . . . ? C1 C2 C3 C4 -9.6(5) . . . . ? C2 C3 C4 C19 -178.4(3) . . . . ? C2 C3 C4 C5 3.8(5) . . . . ? C3 C4 C5 C6 -144.1(3) . . . . ? C19 C4 C5 C6 38.0(4) . . . . ? C3 C4 C5 C20 97.6(3) . . . . ? C19 C4 C5 C20 -80.2(4) . . . . ? C3 C4 C5 C10 -26.8(4) . . . . ? C19 C4 C5 C10 155.4(3) . . . . ? C4 C5 C6 C7 174.0(2) . . . . ? C20 C5 C6 C7 -69.4(3) . . . . ? C10 C5 C6 C7 56.3(3) . . . . ? C5 C6 C7 C8 -60.1(3) . . . . ? C6 C7 C8 C21 -177.8(3) . . . . ? C6 C7 C8 C9 54.0(3) . . . . ? C7 C8 C9 C22 79.6(3) . . . . ? C21 C8 C9 C22 -45.8(3) . . . . ? C7 C8 C9 C10 -46.1(3) . . . . ? C21 C8 C9 C10 -171.5(2) . . . . ? C7 C8 C9 C11 -165.8(2) . . . . ? C21 C8 C9 C11 68.7(3) . . . . ? C2 C1 C10 C9 162.3(2) . . . . ? C2 C1 C10 C5 -64.4(3) . . . . ? C22 C9 C10 C1 52.6(3) . . . . ? C8 C9 C10 C1 177.4(2) . . . . ? C11 C9 C10 C1 -63.8(3) . . . . ? C22 C9 C10 C5 -76.8(3) . . . . ? C8 C9 C10 C5 48.0(3) . . . . ? C11 C9 C10 C5 166.8(2) . . . . ? C6 C5 C10 C1 175.2(3) . . . . ? C4 C5 C10 C1 55.7(3) . . . . ? C20 C5 C10 C1 -63.0(3) . . . . ? C6 C5 C10 C9 -52.7(3) . . . . ? C4 C5 C10 C9 -172.1(2) . . . . ? C20 C5 C10 C9 69.1(3) . . . . ? C22 C9 C11 C12 179.7(2) . . . . ? C10 C9 C11 C12 -59.0(3) . . . . ? C8 C9 C11 C12 61.0(3) . . . . ? C9 C11 C12 C13 83.9(3) . . . . ? C9 C11 C12 C17 -100.2(3) . . . . ? C11 C12 C13 C14 -177.6(2) . . . . ? C17 C12 C13 C14 6.4(4) . . . . ? C12 C13 C14 O1 -178.0(2) . . . . ? C12 C13 C14 C15 3.5(4) . . . . ? C18 N1 C15 C16 7.3(4) . . . . ? C18 N1 C15 C14 -174.5(2) . . . . ? O1 C14 C15 N1 -5.2(3) . . . . ? C13 C14 C15 N1 173.3(2) . . . . ? O1 C14 C15 C16 173.1(2) . . . . ? C13 C14 C15 C16 -8.4(3) . . . . ? N1 C15 C16 C17 -179.1(2) . . . . ? C14 C15 C16 C17 2.9(3) . . . . ? C15 C16 C17 O2 -171.7(2) . . . . ? C15 C16 C17 C12 7.1(4) . . . . ? C13 C12 C17 O2 166.9(2) . . . . ? C11 C12 C17 O2 -9.2(3) . . . . ? C13 C12 C17 C16 -11.9(3) . . . . ? C11 C12 C17 C16 172.0(2) . . . . ? 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 N1 H1A O2 0.86 2.32 2.992(3) 135.1 1_545 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 66.99 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.216 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 974400'