# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_(M)_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N O3' _chemical_formula_sum 'C23 H25 N O3' _chemical_formula_weight 363.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _space_group_name_Hall 'P 2ac 2ab' 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 7.6205(2) _cell_length_b 10.6084(3) _cell_length_c 24.2862(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1963.33(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6438 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 66.57 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6673 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 8473 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 66.54 _reflns_number_total 3399 _reflns_number_gt 3337 _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^)+(0.0305P)^2^+0.3198P] 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 -0.08(15) _refine_ls_number_reflns 3399 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0645 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.59336(12) 0.19823(8) 0.77714(3) 0.0247(2) Uani 1 1 d . . . O2 O 0.90293(12) 0.22814(8) 0.93576(3) 0.0268(2) Uani 1 1 d . . . O3 O 0.79920(12) -0.02874(8) 0.87218(3) 0.0247(2) Uani 1 1 d . . . N1 N 0.72612(13) 0.23726(9) 0.85959(4) 0.0186(2) Uani 1 1 d . . . C1 C 0.64136(17) -0.12376(13) 1.06814(5) 0.0260(3) Uani 1 1 d . . . H1 H 0.6119 -0.1605 1.1026 0.031 Uiso 1 1 calc R . . C2 C 0.6983(2) -0.19980(12) 1.02508(5) 0.0296(3) Uani 1 1 d . . . H2 H 0.7080 -0.2883 1.0301 0.036 Uiso 1 1 calc R . . C3 C 0.74064(19) -0.14635(12) 0.97500(5) 0.0262(3) Uani 1 1 d . . . H3 H 0.7795 -0.1982 0.9455 0.031 Uiso 1 1 calc R . . C4 C 0.72650(16) -0.01657(12) 0.96754(5) 0.0198(2) Uani 1 1 d . . . C5 C 0.76715(15) 0.03515(11) 0.91244(5) 0.0203(2) Uani 1 1 d . . . C6 C 0.79665(16) 0.17800(11) 0.90597(5) 0.0197(3) Uani 1 1 d . . . C7 C 0.59585(16) 0.17965(10) 0.82629(5) 0.0193(2) Uani 1 1 d . . . C8 C 0.45699(16) 0.10307(11) 0.85445(5) 0.0210(3) Uani 1 1 d . . . C9 C 0.39573(17) -0.00779(12) 0.82078(5) 0.0250(3) Uani 1 1 d . . . H9A H 0.4983 -0.0621 0.8129 0.030 Uiso 1 1 calc R . . H9B H 0.3516 0.0241 0.7851 0.030 Uiso 1 1 calc R . . C10 C 0.25404(19) -0.08839(13) 0.84664(6) 0.0336(3) Uani 1 1 d . . . H10A H 0.2953 -0.1205 0.8822 0.050 Uiso 1 1 calc R . . H10B H 0.2269 -0.1594 0.8222 0.050 Uiso 1 1 calc R . . H10C H 0.1482 -0.0375 0.8522 0.050 Uiso 1 1 calc R . . C11 C 0.64021(19) 0.66433(12) 0.84925(5) 0.0264(3) Uani 1 1 d . . . H11A H 0.6206 0.6805 0.8100 0.040 Uiso 1 1 calc R . . H11B H 0.7526 0.7012 0.8604 0.040 Uiso 1 1 calc R . . H11C H 0.5452 0.7024 0.8708 0.040 Uiso 1 1 calc R . . C12 C 0.64372(16) 0.52123(11) 0.85954(5) 0.0204(2) Uani 1 1 d . . . C13 C 0.80255(16) 0.45877(11) 0.83105(5) 0.0180(2) Uani 1 1 d . . . C14 C 0.83941(16) 0.32955(11) 0.83253(5) 0.0181(2) Uani 1 1 d . . . C15 C 0.39060(17) 0.13994(12) 0.90229(5) 0.0250(3) Uani 1 1 d . . . H15A H 0.4310 0.2155 0.9190 0.030 Uiso 1 1 calc R . . H15B H 0.3026 0.0908 0.9198 0.030 Uiso 1 1 calc R . . C16 C 0.62737(16) 0.00542(12) 1.06100(5) 0.0236(3) Uani 1 1 d . . . H16 H 0.5885 0.0570 1.0906 0.028 Uiso 1 1 calc R . . C17 C 0.66985(16) 0.05945(11) 1.01095(5) 0.0212(3) Uani 1 1 d . . . H17 H 0.6605 0.1481 1.0061 0.025 Uiso 1 1 calc R . . C18 C 0.98658(16) 0.27827(11) 0.80737(5) 0.0213(3) Uani 1 1 d . . . H18 H 1.0077 0.1902 0.8100 0.026 Uiso 1 1 calc R . . C19 C 1.10306(17) 0.35355(12) 0.77855(5) 0.0234(3) Uani 1 1 d . . . H19 H 1.2039 0.3183 0.7615 0.028 Uiso 1 1 calc R . . C20 C 1.06903(16) 0.48152(12) 0.77525(5) 0.0230(3) Uani 1 1 d . . . H20 H 1.1461 0.5350 0.7553 0.028 Uiso 1 1 calc R . . C21 C 0.92282(16) 0.53166(12) 0.80106(5) 0.0212(3) Uani 1 1 d . . . H21 H 0.9030 0.6198 0.7983 0.025 Uiso 1 1 calc R . . C22 C 0.47098(16) 0.46931(12) 0.83649(5) 0.0226(3) Uani 1 1 d . . . H22A H 0.3735 0.5229 0.8485 0.034 Uiso 1 1 calc R . . H22B H 0.4528 0.3833 0.8500 0.034 Uiso 1 1 calc R . . H22C H 0.4762 0.4686 0.7962 0.034 Uiso 1 1 calc R . . C23 C 0.65101(17) 0.50017(12) 0.92238(5) 0.0237(3) Uani 1 1 d . . . H23A H 0.5472 0.5379 0.9396 0.036 Uiso 1 1 calc R . . H23B H 0.7571 0.5397 0.9373 0.036 Uiso 1 1 calc R . . H23C H 0.6534 0.4095 0.9302 0.036 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 0.0279(5) 0.0284(4) 0.0179(4) 0.0007(3) -0.0009(4) -0.0062(4) O2 0.0302(5) 0.0273(4) 0.0229(4) 0.0022(4) -0.0070(4) -0.0078(4) O3 0.0290(5) 0.0242(4) 0.0209(4) -0.0028(4) 0.0037(4) 0.0010(4) N1 0.0191(5) 0.0190(5) 0.0179(5) 0.0008(4) 0.0006(4) -0.0023(4) C1 0.0279(7) 0.0302(6) 0.0198(6) 0.0057(5) -0.0010(5) -0.0012(5) C2 0.0442(8) 0.0196(6) 0.0250(6) 0.0023(5) -0.0040(6) -0.0006(6) C3 0.0358(8) 0.0223(6) 0.0206(6) -0.0030(5) -0.0028(6) 0.0005(5) C4 0.0190(6) 0.0212(6) 0.0192(5) -0.0006(5) -0.0025(5) -0.0002(5) C5 0.0183(6) 0.0203(6) 0.0224(6) -0.0015(5) -0.0011(5) -0.0003(5) C6 0.0201(6) 0.0213(6) 0.0178(5) 0.0003(5) 0.0023(5) -0.0007(5) C7 0.0196(6) 0.0185(5) 0.0197(6) -0.0007(5) 0.0009(5) -0.0008(5) C8 0.0200(6) 0.0216(6) 0.0214(6) 0.0039(5) -0.0028(5) -0.0010(5) C9 0.0259(6) 0.0249(6) 0.0242(6) 0.0015(5) -0.0013(5) -0.0058(6) C10 0.0318(8) 0.0296(7) 0.0395(8) 0.0023(6) 0.0005(6) -0.0103(6) C11 0.0290(7) 0.0227(6) 0.0274(6) -0.0011(5) -0.0003(5) 0.0028(5) C12 0.0204(6) 0.0221(6) 0.0187(5) 0.0001(5) -0.0005(5) 0.0013(5) C13 0.0181(6) 0.0218(6) 0.0140(5) -0.0009(5) -0.0033(4) -0.0013(5) C14 0.0181(6) 0.0213(6) 0.0151(5) 0.0000(4) -0.0008(4) -0.0047(5) C15 0.0225(6) 0.0275(6) 0.0251(6) 0.0011(5) 0.0016(5) -0.0024(5) C16 0.0213(6) 0.0302(7) 0.0194(6) -0.0016(5) 0.0006(5) 0.0033(5) C17 0.0198(6) 0.0204(6) 0.0235(6) 0.0000(5) -0.0013(5) 0.0022(5) C18 0.0226(6) 0.0199(6) 0.0213(6) -0.0026(5) -0.0016(5) -0.0005(5) C19 0.0190(6) 0.0300(7) 0.0212(6) -0.0039(5) 0.0020(5) -0.0026(5) C20 0.0202(6) 0.0297(6) 0.0190(6) 0.0030(5) -0.0004(5) -0.0065(5) C21 0.0230(6) 0.0209(6) 0.0198(6) 0.0027(5) -0.0048(5) -0.0026(5) C22 0.0197(6) 0.0256(6) 0.0225(6) -0.0005(5) 0.0005(5) 0.0026(5) C23 0.0242(6) 0.0269(6) 0.0201(6) -0.0024(5) 0.0013(5) 0.0027(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 O1 C7 1.2100(15) . ? O2 C6 1.2093(15) . ? O3 C5 1.2143(15) . ? N1 C6 1.3974(15) . ? N1 C7 1.4188(16) . ? N1 C14 1.4614(15) . ? C1 C16 1.3854(19) . ? C1 C2 1.3902(19) . ? C1 H1 0.9500 . ? C2 C3 1.3802(19) . ? C2 H2 0.9500 . ? C3 C4 1.3928(18) . ? C3 H3 0.9500 . ? C4 C17 1.3958(17) . ? C4 C5 1.4791(16) . ? C5 C6 1.5400(16) . ? C7 C8 1.4990(17) . ? C8 C15 1.3263(18) . ? C8 C9 1.5066(17) . ? C9 C10 1.5138(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.5388(17) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C22 1.5328(17) . ? C12 C23 1.5433(16) . ? C12 C13 1.5436(17) . ? C13 C14 1.3998(17) . ? C13 C21 1.4030(17) . ? C14 C18 1.3882(17) . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? C16 C17 1.3823(18) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.3840(18) . ? C18 H18 0.9500 . ? C19 C20 1.3844(18) . ? C19 H19 0.9500 . ? C20 C21 1.3847(18) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C6 N1 C7 122.33(9) . . ? C6 N1 C14 115.89(10) . . ? C7 N1 C14 116.47(9) . . ? C16 C1 C2 120.25(12) . . ? C16 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 119.83(12) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.18(12) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C17 119.78(11) . . ? C3 C4 C5 117.92(11) . . ? C17 C4 C5 122.27(11) . . ? O3 C5 C4 124.30(11) . . ? O3 C5 C6 115.96(11) . . ? C4 C5 C6 119.20(10) . . ? O2 C6 N1 122.81(11) . . ? O2 C6 C5 118.01(11) . . ? N1 C6 C5 117.95(10) . . ? O1 C7 N1 120.20(11) . . ? O1 C7 C8 121.82(11) . . ? N1 C7 C8 117.86(10) . . ? C15 C8 C7 120.60(11) . . ? C15 C8 C9 125.98(12) . . ? C7 C8 C9 113.22(10) . . ? C8 C9 C10 115.90(11) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C22 C12 C11 106.27(10) . . ? C22 C12 C23 109.88(10) . . ? C11 C12 C23 107.70(10) . . ? C22 C12 C13 110.82(9) . . ? C11 C12 C13 111.37(10) . . ? C23 C12 C13 110.66(10) . . ? C14 C13 C21 114.96(11) . . ? C14 C13 C12 124.49(11) . . ? C21 C13 C12 120.56(10) . . ? C18 C14 C13 122.32(11) . . ? C18 C14 N1 114.37(10) . . ? C13 C14 N1 123.30(11) . . ? C8 C15 H15A 120.0 . . ? C8 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C17 C16 C1 120.15(12) . . ? C17 C16 H16 119.9 . . ? C1 C16 H16 119.9 . . ? C16 C17 C4 119.81(11) . . ? C16 C17 H17 120.1 . . ? C4 C17 H17 120.1 . . ? C19 C18 C14 120.97(11) . . ? C19 C18 H18 119.5 . . ? C14 C18 H18 119.5 . . ? C18 C19 C20 118.36(12) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? C19 C20 C21 120.08(11) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C13 123.29(11) . . ? C20 C21 H21 118.4 . . ? C13 C21 H21 118.4 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C12 C23 H23A 109.5 . . ? C12 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C12 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 66.54 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.119 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 942921' ####################################################################### # # 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_(P)_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N O3' _chemical_formula_sum 'C23 H25 N O3' _chemical_formula_weight 363.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _space_group_name_Hall 'P 2ac 2ab' 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 7.6186(2) _cell_length_b 10.6097(2) _cell_length_c 24.3166(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1965.54(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9961 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 66.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6862 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 15043 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 66.55 _reflns_number_total 3429 _reflns_number_gt 3403 _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^)+(0.0336P)^2^+0.3406P] 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 -0.04(15) _refine_ls_number_reflns 3429 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.79845(12) -0.02905(8) 0.12778(3) 0.0282(2) Uani 1 1 d . . . O2 O 0.59255(12) 0.19795(8) 0.22280(3) 0.0274(2) Uani 1 1 d . . . O3 O 0.90249(12) 0.22751(8) 0.06447(3) 0.0300(2) Uani 1 1 d . . . C1 C 0.64142(18) -0.12321(13) -0.06807(5) 0.0291(3) Uani 1 1 d . . . H1 H 0.6124 -0.1599 -0.1025 0.035 Uiso 1 1 calc R . . C2 C 0.6977(2) -0.19918(12) -0.02510(5) 0.0329(3) Uani 1 1 d . . . H2 H 0.7074 -0.2877 -0.0302 0.040 Uiso 1 1 calc R . . C3 C 0.73962(19) -0.14608(12) 0.02499(5) 0.0298(3) Uani 1 1 d . . . H3 H 0.7781 -0.1981 0.0544 0.036 Uiso 1 1 calc R . . C4 C 0.72566(16) -0.01643(12) 0.03247(5) 0.0229(2) Uani 1 1 d . . . C5 C 0.76674(15) 0.03496(11) 0.08759(5) 0.0233(2) Uani 1 1 d . . . C6 C 0.79608(16) 0.17757(11) 0.09414(5) 0.0226(3) Uani 1 1 d . . . N1 N 0.72592(13) 0.23669(9) 0.14055(4) 0.0210(2) Uani 1 1 d . . . C8 C 0.83926(15) 0.32896(11) 0.16753(5) 0.0205(2) Uani 1 1 d . . . C9 C 0.80279(16) 0.45815(11) 0.16897(5) 0.0204(2) Uani 1 1 d . . . C10 C 0.64427(16) 0.52064(11) 0.14044(5) 0.0229(2) Uani 1 1 d . . . C11 C 0.65134(17) 0.49948(12) 0.07771(5) 0.0263(3) Uani 1 1 d . . . H11A H 0.6526 0.4088 0.0700 0.039 Uiso 1 1 calc R . . H11B H 0.7579 0.5383 0.0628 0.039 Uiso 1 1 calc R . . H11C H 0.5480 0.5379 0.0605 0.039 Uiso 1 1 calc R . . C12 C 0.59546(16) 0.17937(11) 0.17380(5) 0.0222(2) Uani 1 1 d . . . C13 C 0.45670(16) 0.10262(12) 0.14555(5) 0.0242(3) Uani 1 1 d . . . C14 C 0.39071(17) 0.13967(13) 0.09774(5) 0.0285(3) Uani 1 1 d . . . H14A H 0.4312 0.2153 0.0811 0.034 Uiso 1 1 calc R . . H14B H 0.3029 0.0906 0.0801 0.034 Uiso 1 1 calc R . . C15 C 0.39487(17) -0.00806(12) 0.17920(5) 0.0285(3) Uani 1 1 d . . . H15A H 0.3503 0.0241 0.2148 0.034 Uiso 1 1 calc R . . H15B H 0.4974 -0.0623 0.1872 0.034 Uiso 1 1 calc R . . C16 C 0.25365(19) -0.08893(14) 0.15345(6) 0.0370(3) Uani 1 1 d . . . H16A H 0.1483 -0.0379 0.1472 0.056 Uiso 1 1 calc R . . H16B H 0.2252 -0.1589 0.1782 0.056 Uiso 1 1 calc R . . H16C H 0.2959 -0.1224 0.1183 0.056 Uiso 1 1 calc R . . C17 C 0.98676(16) 0.27763(11) 0.19268(5) 0.0239(3) Uani 1 1 d . . . H17 H 1.0078 0.1896 0.1901 0.029 Uiso 1 1 calc R . . C18 C 1.10301(17) 0.35280(12) 0.22135(5) 0.0260(3) Uani 1 1 d . . . H18 H 1.2038 0.3175 0.2384 0.031 Uiso 1 1 calc R . . C19 C 1.06954(16) 0.48067(12) 0.22465(5) 0.0256(3) Uani 1 1 d . . . H19 H 1.1469 0.5340 0.2446 0.031 Uiso 1 1 calc R . . C20 C 0.92321(16) 0.53092(12) 0.19889(5) 0.0235(3) Uani 1 1 d . . . H20 H 0.9034 0.6191 0.2016 0.028 Uiso 1 1 calc R . . C21 C 0.47106(16) 0.46898(12) 0.16349(5) 0.0252(3) Uani 1 1 d . . . H21A H 0.4527 0.3829 0.1500 0.038 Uiso 1 1 calc R . . H21B H 0.3737 0.5226 0.1514 0.038 Uiso 1 1 calc R . . H21C H 0.4761 0.4684 0.2038 0.038 Uiso 1 1 calc R . . C22 C 0.64120(19) 0.66375(12) 0.15062(5) 0.0295(3) Uani 1 1 d . . . H22A H 0.5463 0.7019 0.1291 0.044 Uiso 1 1 calc R . . H22B H 0.7537 0.7004 0.1394 0.044 Uiso 1 1 calc R . . H22C H 0.6216 0.6801 0.1898 0.044 Uiso 1 1 calc R . . C23 C 0.66956(16) 0.05989(11) -0.01091(5) 0.0241(3) Uani 1 1 d . . . H23 H 0.6604 0.1485 -0.0060 0.029 Uiso 1 1 calc R . . C24 C 0.62745(16) 0.00589(12) -0.06095(5) 0.0263(3) Uani 1 1 d . . . H24 H 0.5889 0.0575 -0.0905 0.032 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 0.0321(5) 0.0280(4) 0.0243(4) 0.0031(4) -0.0044(4) 0.0016(4) O2 0.0302(5) 0.0307(4) 0.0213(4) -0.0003(3) 0.0010(4) -0.0065(4) O3 0.0332(5) 0.0302(5) 0.0265(4) -0.0027(4) 0.0077(4) -0.0079(4) C1 0.0309(7) 0.0327(7) 0.0236(6) -0.0059(5) 0.0004(5) -0.0003(6) C2 0.0479(8) 0.0224(6) 0.0285(6) -0.0022(5) 0.0047(6) -0.0011(6) C3 0.0400(8) 0.0255(6) 0.0238(6) 0.0030(5) 0.0026(6) 0.0003(6) C4 0.0225(6) 0.0237(6) 0.0226(5) 0.0006(5) 0.0026(5) -0.0015(5) C5 0.0198(6) 0.0246(6) 0.0255(6) 0.0008(5) 0.0010(5) 0.0002(5) C6 0.0228(6) 0.0237(6) 0.0213(5) 0.0001(5) -0.0026(5) -0.0008(5) N1 0.0210(5) 0.0208(5) 0.0210(4) -0.0004(4) -0.0006(4) -0.0018(4) C8 0.0195(6) 0.0241(6) 0.0178(5) 0.0000(4) 0.0007(4) -0.0042(5) C9 0.0194(6) 0.0246(6) 0.0173(5) 0.0004(5) 0.0036(4) -0.0013(5) C10 0.0223(6) 0.0244(6) 0.0220(5) -0.0001(5) 0.0011(5) 0.0016(5) C11 0.0257(6) 0.0301(6) 0.0230(6) 0.0032(5) -0.0013(5) 0.0027(5) C12 0.0211(6) 0.0215(5) 0.0240(6) 0.0010(5) -0.0007(5) -0.0004(5) C13 0.0219(6) 0.0254(6) 0.0254(6) -0.0048(5) 0.0030(5) -0.0009(5) C14 0.0249(6) 0.0322(6) 0.0282(6) -0.0012(5) -0.0019(5) -0.0034(6) C15 0.0292(6) 0.0278(6) 0.0286(6) -0.0013(5) 0.0014(5) -0.0067(6) C16 0.0342(8) 0.0329(7) 0.0441(8) -0.0031(6) -0.0011(6) -0.0106(6) C17 0.0244(6) 0.0229(6) 0.0244(6) 0.0033(5) 0.0010(5) -0.0004(5) C18 0.0204(6) 0.0333(7) 0.0243(6) 0.0045(5) -0.0017(5) -0.0021(5) C19 0.0215(6) 0.0332(6) 0.0220(6) -0.0029(5) 0.0007(5) -0.0061(5) C20 0.0246(6) 0.0231(6) 0.0228(6) -0.0034(5) 0.0052(5) -0.0030(5) C21 0.0210(6) 0.0291(6) 0.0256(6) 0.0006(5) -0.0008(5) 0.0027(5) C22 0.0316(7) 0.0252(6) 0.0317(7) 0.0011(5) 0.0008(6) 0.0032(5) C23 0.0221(6) 0.0223(6) 0.0279(6) -0.0001(5) 0.0015(5) 0.0021(5) C24 0.0230(6) 0.0327(7) 0.0231(6) 0.0012(5) -0.0018(5) 0.0034(6) _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 C5 1.2143(15) . ? O2 C12 1.2079(15) . ? O3 C6 1.2077(15) . ? C1 C24 1.3848(19) . ? C1 C2 1.3876(19) . ? C1 H1 0.9500 . ? C2 C3 1.3795(19) . ? C2 H2 0.9500 . ? C3 C4 1.3917(18) . ? C3 H3 0.9500 . ? C4 C23 1.3968(17) . ? C4 C5 1.4803(16) . ? C5 C6 1.5378(16) . ? C6 N1 1.3974(15) . ? N1 C12 1.4183(16) . ? N1 C8 1.4610(15) . ? C8 C17 1.3904(17) . ? C8 C9 1.3990(16) . ? C9 C20 1.4026(17) . ? C9 C10 1.5425(17) . ? C10 C21 1.5350(17) . ? C10 C22 1.5385(17) . ? C10 C11 1.5426(16) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.5009(17) . ? C13 C14 1.3261(18) . ? C13 C15 1.5069(17) . ? C14 H14A 0.9500 . ? C14 H14B 0.9500 . ? C15 C16 1.5119(18) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.3808(18) . ? C17 H17 0.9500 . ? C18 C19 1.3827(18) . ? C18 H18 0.9500 . ? C19 C20 1.3854(18) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.3828(18) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 C24 C1 C2 120.27(12) . . ? C24 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 119.95(12) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.09(12) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C23 119.85(11) . . ? C3 C4 C5 117.79(11) . . ? C23 C4 C5 122.34(11) . . ? O1 C5 C4 124.38(11) . . ? O1 C5 C6 115.97(11) . . ? C4 C5 C6 119.14(10) . . ? O3 C6 N1 122.85(11) . . ? O3 C6 C5 117.86(11) . . ? N1 C6 C5 118.02(10) . . ? C6 N1 C12 122.42(9) . . ? C6 N1 C8 115.93(9) . . ? C12 N1 C8 116.45(9) . . ? C17 C8 C9 122.23(11) . . ? C17 C8 N1 114.38(10) . . ? C9 C8 N1 123.39(10) . . ? C8 C9 C20 114.98(11) . . ? C8 C9 C10 124.43(11) . . ? C20 C9 C10 120.58(10) . . ? C21 C10 C22 106.29(10) . . ? C21 C10 C9 110.81(9) . . ? C22 C10 C9 111.33(10) . . ? C21 C10 C11 109.82(10) . . ? C22 C10 C11 107.66(10) . . ? C9 C10 C11 110.78(9) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 N1 120.35(11) . . ? O2 C12 C13 121.81(11) . . ? N1 C12 C13 117.72(10) . . ? C14 C13 C12 120.50(11) . . ? C14 C13 C15 126.05(12) . . ? C12 C13 C15 113.22(10) . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C13 C15 C16 116.09(11) . . ? C13 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C13 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C8 120.95(11) . . ? C18 C17 H17 119.5 . . ? C8 C17 H17 119.5 . . ? C17 C18 C19 118.53(12) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C18 C19 C20 119.99(11) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C9 123.30(11) . . ? C19 C20 H20 118.3 . . ? C9 C20 H20 118.4 . . ? C10 C21 H21A 109.5 . . ? C10 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C10 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C10 C22 H22A 109.5 . . ? C10 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C10 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C4 119.70(11) . . ? C24 C23 H23 120.2 . . ? C4 C23 H23 120.2 . . ? C23 C24 C1 120.14(11) . . ? C23 C24 H24 119.9 . . ? C1 C24 H24 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 66.55 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.166 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.030 _database_code_depnum_ccdc_archive 'CCDC 942922' ####################################################################### # # 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_(R,R,M)_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H31 N O3' _chemical_formula_sum 'C26 H31 N O3' _chemical_formula_weight 405.52 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) _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4837(3) _cell_length_b 11.0800(3) _cell_length_c 11.5198(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.7490(10) _cell_angle_gamma 90.00 _cell_volume 1159.14(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9842 _cell_measurement_theta_min 4.01 _cell_measurement_theta_max 67.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.594 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8657 _exptl_absorpt_correction_T_max 0.9602 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 12752 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 67.44 _reflns_number_total 3872 _reflns_number_gt 3856 _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^)+(0.0378P)^2^+0.8732P] 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 0.01(35) _chemical_absolute_configuration ad _refine_ls_number_reflns 3872 _refine_ls_number_parameters 368 _refine_ls_number_restraints 441 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 1.243 _refine_ls_restrained_S_all 1.208 _refine_ls_shift/su_max 0.003 _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 0.2194(4) 0.9217(3) 0.6055(2) 0.0802(11) Uani 1 1 d U . . O2 O 0.5707(3) 0.67562(19) 0.53712(19) 0.0414(5) Uani 1 1 d U . . O3 O 0.5627(3) 0.84264(19) 0.78733(17) 0.0426(6) Uani 1 1 d U . . N1 N 0.3831(3) 0.7865(2) 0.5698(2) 0.0324(5) Uani 1 1 d U . . C1 C 0.7876(4) 0.7898(4) 0.7294(3) 0.0594(10) Uani 1 1 d U . . H1A H 0.8466 0.8444 0.7915 0.089 Uiso 1 1 calc R . . H1B H 0.8279 0.7878 0.6601 0.089 Uiso 1 1 calc R . . H1C H 0.7903 0.7084 0.7634 0.089 Uiso 1 1 calc R . . C2 C 0.1460(5) 0.7991(4) 0.1278(3) 0.0612(11) Uani 1 1 d U . . C3 C 0.1577(4) 0.7437(3) 0.2529(3) 0.0477(9) Uani 1 1 d U D . C4 C 0.2612(4) 0.7818(3) 0.3572(2) 0.0335(7) Uani 1 1 d U . . H4 H 0.3281 0.8438 0.3518 0.040 Uiso 1 1 calc R D . C5 C 0.0696(4) 0.6057(3) 0.3801(3) 0.0465(8) Uani 1 1 d U D . H5 H 0.0001 0.5458 0.3856 0.056 Uiso 1 1 calc R . . C6 C 0.1765(4) 0.6412(3) 0.4859(3) 0.0374(7) Uani 1 1 d U . . C7 C 0.2705(3) 0.7319(3) 0.4700(2) 0.0316(6) Uani 1 1 d U D . C8 C 0.1786(4) 0.5784(3) 0.6067(3) 0.0477(9) Uani 1 1 d U C . C9 C 0.3444(5) 0.8872(3) 0.6288(3) 0.0451(9) Uani 1 1 d U . . C10 C 0.5303(4) 0.7558(3) 0.5916(2) 0.0358(7) Uani 1 1 d U . . C11 C 0.6331(4) 0.8332(3) 0.6890(3) 0.0425(8) Uani 1 1 d U B . C12 C 0.4751(5) 0.9442(3) 0.7211(3) 0.0484(9) Uani 1 1 d U B . C13 C 0.4381(6) 1.0373(3) 0.7995(3) 0.0589(11) Uani 1 1 d U . . C14 C 0.4656(4) 1.0207(3) 0.9224(3) 0.0418(8) Uani 1 1 d U B . H14 H 0.5097 0.9476 0.9583 0.050 Uiso 1 1 calc R . . C15 C 0.4303(4) 1.1080(4) 0.9940(3) 0.0494(9) Uani 1 1 d U . . H15 H 0.4258 1.0887 1.0732 0.059 Uiso 1 1 calc R A 1 C17 C 0.0612(5) 0.6543(3) 0.2679(3) 0.0540(10) Uani 1 1 d U . . H17 H -0.0127 0.6258 0.1989 0.065 Uiso 1 1 calc R D . C18 C 0.5951(5) 0.9672(3) 0.6577(3) 0.0576(10) Uani 1 1 d U . . H18A H 0.6724 1.0251 0.6999 0.069 Uiso 1 1 calc R B . H18B H 0.5575 0.9848 0.5699 0.069 Uiso 1 1 calc R . . C19A C 0.3942(9) 1.2373(6) 0.8350(6) 0.041(2) Uani 0.465(8) 1 d PU B 1 H19A H 0.3650 1.3158 0.8040 0.050 Uiso 0.465(8) 1 calc PR B 1 C20A C 0.4259(9) 1.1501(6) 0.7585(5) 0.0299(17) Uani 0.465(8) 1 d PU B 1 H20A H 0.4379 1.1702 0.6818 0.036 Uiso 0.465(8) 1 calc PR B 1 C16A C 0.4042(10) 1.2123(8) 0.9543(6) 0.0363(18) Uani 0.465(8) 1 d PU B 1 H16A H 0.3912 1.2752 1.0064 0.044 Uiso 0.465(8) 1 calc PR B 1 C19B C 0.2832(7) 1.2223(5) 0.8089(5) 0.0298(15) Uani 0.535(8) 1 d PU B 2 H19B H 0.2267 1.2896 0.7704 0.036 Uiso 0.535(8) 1 calc PR B 2 C20B C 0.3215(8) 1.1353(5) 0.7394(5) 0.0287(15) Uani 0.535(8) 1 d PU B 2 H20B H 0.2769 1.1344 0.6543 0.034 Uiso 0.535(8) 1 calc PR B 2 C16B C 0.3246(10) 1.2145(6) 0.9323(7) 0.0374(16) Uani 0.535(8) 1 d PU B 2 H16B H 0.2908 1.2716 0.9798 0.045 Uiso 0.535(8) 1 calc PR B 2 C21A C 0.3353(7) 0.5099(6) 0.6528(5) 0.0333(15) Uani 0.487(5) 1 d PU C 3 H21A H 0.3500 0.4809 0.7358 0.050 Uiso 0.487(5) 1 calc PR C 3 H21B H 0.4145 0.5661 0.6511 0.050 Uiso 0.487(5) 1 calc PR C 3 H21C H 0.3364 0.4413 0.5994 0.050 Uiso 0.487(5) 1 calc PR C 3 C22A C 0.0656(7) 0.5062(6) 0.6099(6) 0.0387(16) Uani 0.487(5) 1 d PU C 3 H22A H 0.0578 0.4397 0.5523 0.058 Uiso 0.487(5) 1 calc PR C 3 H22B H -0.0261 0.5529 0.5880 0.058 Uiso 0.487(5) 1 calc PR C 3 H22C H 0.0829 0.4735 0.6919 0.058 Uiso 0.487(5) 1 calc PR C 3 C23A C 0.2064(9) 0.6806(7) 0.7194(6) 0.0436(18) Uani 0.487(5) 1 d PU C 3 H23A H 0.1345 0.7461 0.6948 0.065 Uiso 0.487(5) 1 calc PR C 3 H23B H 0.3062 0.7136 0.7364 0.065 Uiso 0.487(5) 1 calc PR C 3 H23C H 0.1948 0.6416 0.7924 0.065 Uiso 0.487(5) 1 calc PR C 3 C21B C 0.2946(7) 0.5885(6) 0.7074(5) 0.0394(16) Uani 0.513(5) 1 d PU C 4 H21D H 0.2809 0.5339 0.7702 0.059 Uiso 0.513(5) 1 calc PR C 4 H21E H 0.3017 0.6718 0.7370 0.059 Uiso 0.513(5) 1 calc PR C 4 H21F H 0.3854 0.5670 0.6877 0.059 Uiso 0.513(5) 1 calc PR C 4 C22B C 0.1491(8) 0.4306(6) 0.5752(6) 0.0424(17) Uani 0.513(5) 1 d PU C 4 H22D H 0.1440 0.3877 0.6482 0.064 Uiso 0.513(5) 1 calc PR C 4 H22E H 0.2300 0.3978 0.5478 0.064 Uiso 0.513(5) 1 calc PR C 4 H22F H 0.0561 0.4203 0.5112 0.064 Uiso 0.513(5) 1 calc PR C 4 C23B C 0.0241(7) 0.6172(6) 0.6269(5) 0.0389(15) Uani 0.513(5) 1 d PU C 4 H23D H -0.0567 0.5905 0.5575 0.058 Uiso 0.513(5) 1 calc PR C 4 H23E H 0.0207 0.7052 0.6343 0.058 Uiso 0.513(5) 1 calc PR C 4 H23F H 0.0142 0.5795 0.7011 0.058 Uiso 0.513(5) 1 calc PR C 4 C24A C 0.1515(13) 0.7095(18) 0.0413(18) 0.042(3) Uani 0.499(7) 1 d PU D 5 H24A H 0.0754 0.6487 0.0379 0.063 Uiso 0.499(7) 1 calc PR D 5 H24B H 0.2486 0.6710 0.0648 0.063 Uiso 0.499(7) 1 calc PR D 5 H24C H 0.1343 0.7471 -0.0386 0.063 Uiso 0.499(7) 1 calc PR D 5 C25A C 0.2287(7) 0.9126(7) 0.1349(6) 0.0405(19) Uani 0.499(7) 1 d PU D 5 H25A H 0.2092 0.9475 0.0536 0.061 Uiso 0.499(7) 1 calc PR D 5 H25B H 0.3343 0.8964 0.1679 0.061 Uiso 0.499(7) 1 calc PR D 5 H25C H 0.1977 0.9695 0.1878 0.061 Uiso 0.499(7) 1 calc PR D 5 C26A C -0.0366(8) 0.8618(6) 0.0780(6) 0.0359(17) Uani 0.499(7) 1 d PU D 5 H26A H -0.0499 0.9193 0.1386 0.054 Uiso 0.499(7) 1 calc PR D 5 H26B H -0.1093 0.7968 0.0678 0.054 Uiso 0.499(7) 1 calc PR D 5 H26C H -0.0501 0.9034 0.0004 0.054 Uiso 0.499(7) 1 calc PR D 5 C24B C 0.1003(15) 0.6995(18) 0.0276(19) 0.047(3) Uani 0.501(7) 1 d PU D 6 H24D H -0.0038 0.6793 0.0138 0.070 Uiso 0.501(7) 1 calc PR D 6 H24E H 0.1605 0.6272 0.0542 0.070 Uiso 0.501(7) 1 calc PR D 6 H24F H 0.1157 0.7297 -0.0478 0.070 Uiso 0.501(7) 1 calc PR D 6 C25B C 0.3260(8) 0.8199(8) 0.1223(6) 0.054(2) Uani 0.501(7) 1 d PU D 6 H25D H 0.3247 0.8472 0.0411 0.081 Uiso 0.501(7) 1 calc PR D 6 H25E H 0.3799 0.7435 0.1406 0.081 Uiso 0.501(7) 1 calc PR D 6 H25F H 0.3746 0.8809 0.1822 0.081 Uiso 0.501(7) 1 calc PR D 6 C26B C 0.0776(11) 0.8981(8) 0.1055(7) 0.057(3) Uani 0.501(7) 1 d PU D 6 H26D H 0.0848 0.9301 0.0281 0.086 Uiso 0.501(7) 1 calc PR D 6 H26E H 0.1212 0.9558 0.1704 0.086 Uiso 0.501(7) 1 calc PR D 6 H26F H -0.0261 0.8852 0.1008 0.086 Uiso 0.501(7) 1 calc PR D 6 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 0.107(2) 0.082(2) 0.0324(13) -0.0153(13) -0.0098(14) 0.0676(19) O2 0.0527(13) 0.0329(12) 0.0361(11) -0.0042(10) 0.0087(10) 0.0095(10) O3 0.0765(16) 0.0248(10) 0.0217(9) 0.0044(8) 0.0066(10) -0.0066(11) N1 0.0508(15) 0.0240(12) 0.0211(10) -0.0006(9) 0.0083(10) 0.0066(10) C1 0.064(2) 0.067(3) 0.0415(19) 0.0059(18) 0.0062(18) -0.0099(19) C2 0.102(3) 0.050(2) 0.0241(15) 0.0064(15) 0.0061(18) -0.033(2) C3 0.079(3) 0.0356(18) 0.0258(14) 0.0029(13) 0.0115(15) -0.0174(17) C4 0.0509(18) 0.0244(14) 0.0267(14) -0.0011(11) 0.0136(13) -0.0039(13) C5 0.060(2) 0.0380(18) 0.0409(17) 0.0068(14) 0.0143(15) -0.0148(16) C6 0.0516(19) 0.0314(16) 0.0332(15) 0.0043(12) 0.0184(13) 0.0050(13) C7 0.0463(17) 0.0261(14) 0.0227(13) -0.0020(11) 0.0103(12) 0.0053(13) C8 0.077(2) 0.0378(19) 0.0403(18) 0.0112(15) 0.0355(17) 0.0175(17) C9 0.083(3) 0.0287(16) 0.0186(13) 0.0015(12) 0.0074(15) 0.0200(17) C10 0.0584(19) 0.0241(15) 0.0216(13) 0.0054(11) 0.0062(13) 0.0028(13) C11 0.063(2) 0.0323(17) 0.0273(14) 0.0053(13) 0.0047(14) -0.0066(15) C12 0.102(3) 0.0196(14) 0.0213(15) 0.0034(12) 0.0138(16) 0.0021(16) C13 0.127(4) 0.0208(16) 0.0311(16) -0.0027(13) 0.0269(19) -0.0012(18) C14 0.061(2) 0.0403(18) 0.0268(15) -0.0031(13) 0.0177(14) -0.0177(15) C15 0.069(2) 0.052(2) 0.0303(16) -0.0095(15) 0.0193(16) -0.0252(18) C17 0.077(3) 0.047(2) 0.0324(16) 0.0000(15) 0.0068(16) -0.0267(19) C18 0.115(3) 0.0260(17) 0.0284(16) 0.0022(13) 0.0145(18) -0.0120(18) C19A 0.047(6) 0.029(3) 0.037(3) -0.004(3) -0.007(3) 0.016(3) C20A 0.034(5) 0.028(3) 0.024(3) -0.002(2) 0.003(3) 0.001(3) C16A 0.028(4) 0.047(4) 0.025(3) -0.024(3) -0.007(3) 0.002(4) C19B 0.025(4) 0.028(3) 0.042(3) 0.000(2) 0.017(2) 0.002(2) C20B 0.032(4) 0.026(3) 0.033(3) -0.005(2) 0.016(2) -0.004(2) C16B 0.038(4) 0.038(3) 0.041(3) -0.019(3) 0.018(3) -0.019(3) C21A 0.047(3) 0.032(3) 0.029(3) 0.007(3) 0.025(3) -0.007(3) C22A 0.044(3) 0.048(4) 0.027(3) 0.006(3) 0.015(3) 0.002(3) C23A 0.066(5) 0.041(4) 0.030(3) 0.000(3) 0.024(3) 0.000(3) C21B 0.055(4) 0.034(3) 0.033(3) 0.010(3) 0.018(3) 0.007(3) C22B 0.054(4) 0.038(3) 0.037(3) 0.006(3) 0.017(3) -0.005(3) C23B 0.043(3) 0.043(4) 0.032(3) 0.007(3) 0.012(3) -0.002(3) C24A 0.045(7) 0.056(5) 0.028(6) 0.010(4) 0.015(6) 0.006(6) C25A 0.035(4) 0.054(4) 0.033(3) 0.015(3) 0.010(3) -0.006(3) C26A 0.034(4) 0.042(4) 0.035(3) 0.009(3) 0.015(3) 0.008(3) C24B 0.057(8) 0.055(6) 0.025(4) -0.001(4) 0.007(7) 0.004(7) C25B 0.042(4) 0.086(6) 0.031(3) 0.014(4) 0.007(3) -0.007(4) C26B 0.084(7) 0.060(5) 0.041(4) 0.023(3) 0.039(5) 0.024(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 O1 C9 1.200(5) . ? O2 C10 1.212(4) . ? O3 C12 1.474(4) . ? O3 C11 1.475(4) . ? N1 C10 1.388(4) . ? N1 C9 1.410(4) . ? N1 C7 1.456(4) . ? C1 C11 1.484(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C26B 1.263(9) . ? C2 C24A 1.418(18) . ? C2 C25A 1.473(7) . ? C2 C3 1.540(4) . ? C2 C24B 1.564(17) . ? C2 C25B 1.741(8) . ? C2 C26A 1.800(8) . ? C3 C4 1.380(4) . ? C3 C17 1.393(5) . ? C4 C7 1.391(4) . ? C4 H4 0.9500 . ? C5 C17 1.381(5) . ? C5 C6 1.398(5) . ? C5 H5 0.9500 . ? C6 C7 1.391(4) . ? C6 C8 1.551(4) . ? C8 C22A 1.346(8) . ? C8 C21B 1.354(7) . ? C8 C23B 1.606(7) . ? C8 C21A 1.616(7) . ? C8 C22B 1.683(7) . ? C8 C23A 1.685(7) . ? C9 C12 1.518(5) . ? C10 C11 1.521(4) . ? C11 C18 1.546(5) . ? C12 C13 1.478(5) . ? C12 C18 1.541(6) . ? C13 C20A 1.330(7) . ? C13 C14 1.376(4) . ? C13 C20B 1.562(7) . ? C14 C15 1.374(5) . ? C14 H14 0.9500 . ? C15 C16A 1.242(9) . ? C15 C16B 1.578(10) . ? C15 H15 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19A C16A 1.378(11) . ? C19A C20A 1.397(9) . ? C19A H19A 0.9500 . ? C20A H20A 0.9500 . ? C16A H16A 0.9500 . ? C19B C16B 1.365(9) . ? C19B C20B 1.367(7) . ? C19B H19B 0.9500 . ? C20B H20B 0.9500 . ? C16B H16B 0.9500 . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 0.9800 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? C24A H24A 0.9800 . ? C24A H24B 0.9800 . ? C24A H24C 0.9800 . ? C25A H25A 0.9800 . ? C25A H25B 0.9800 . ? C25A H25C 0.9800 . ? C26A H26A 0.9800 . ? C26A H26B 0.9800 . ? C26A H26C 0.9800 . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? C25B H25D 0.9800 . ? C25B H25E 0.9800 . ? C25B H25F 0.9800 . ? C26B H26D 0.9800 . ? C26B H26E 0.9800 . ? C26B 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 C12 O3 C11 88.2(2) . . ? C10 N1 C9 119.7(3) . . ? C10 N1 C7 120.8(2) . . ? C9 N1 C7 118.4(3) . . ? C11 C1 H1A 109.5 . . ? C11 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C11 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C26B C2 C24A 125.9(9) . . ? C26B C2 C25A 60.2(6) . . ? C24A C2 C25A 120.6(8) . . ? C26B C2 C3 115.5(5) . . ? C24A C2 C3 111.8(9) . . ? C25A C2 C3 113.3(3) . . ? C26B C2 C24B 116.5(9) . . ? C24A C2 C24B 17.6(8) . . ? C25A C2 C24B 132.3(9) . . ? C3 C2 C24B 109.8(9) . . ? C26B C2 C25B 109.2(6) . . ? C24A C2 C25B 80.4(6) . . ? C25A C2 C25B 51.4(4) . . ? C3 C2 C25B 106.3(4) . . ? C24B C2 C25B 97.6(7) . . ? C26B C2 C26A 37.7(5) . . ? C24A C2 C26A 105.8(7) . . ? C25A C2 C26A 97.8(4) . . ? C3 C2 C26A 104.8(4) . . ? C24B C2 C26A 90.0(7) . . ? C25B C2 C26A 143.2(4) . . ? C4 C3 C17 115.9(3) . . ? C4 C3 C2 122.3(3) . . ? C17 C3 C2 121.8(3) . . ? C3 C4 C7 122.0(3) . . ? C3 C4 H4 119.0 . . ? C7 C4 H4 119.0 . . ? C17 C5 C6 122.5(3) . . ? C17 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C7 C6 C5 114.8(3) . . ? C7 C6 C8 126.8(3) . . ? C5 C6 C8 118.3(3) . . ? C6 C7 C4 122.7(3) . . ? C6 C7 N1 123.2(3) . . ? C4 C7 N1 114.1(3) . . ? C22A C8 C21B 118.8(4) . . ? C22A C8 C6 119.1(4) . . ? C21B C8 C6 121.9(4) . . ? C22A C8 C23B 52.3(4) . . ? C21B C8 C23B 113.8(4) . . ? C6 C8 C23B 103.5(3) . . ? C22A C8 C21A 112.1(4) . . ? C21B C8 C21A 46.6(4) . . ? C6 C8 C21A 106.2(3) . . ? C23B C8 C21A 150.3(4) . . ? C22A C8 C22B 49.0(4) . . ? C21B C8 C22B 108.0(4) . . ? C6 C8 C22B 106.5(3) . . ? C23B C8 C22B 100.9(4) . . ? C21A C8 C22B 72.2(4) . . ? C22A C8 C23A 109.1(4) . . ? C21B C8 C23A 51.4(4) . . ? C6 C8 C23A 110.4(3) . . ? C23B C8 C23A 69.9(4) . . ? C21A C8 C23A 97.9(4) . . ? C22B C8 C23A 143.1(4) . . ? O1 C9 N1 121.5(3) . . ? O1 C9 C12 125.4(3) . . ? N1 C9 C12 113.2(3) . . ? O2 C10 N1 122.5(3) . . ? O2 C10 C11 124.4(3) . . ? N1 C10 C11 113.1(3) . . ? O3 C11 C1 114.0(3) . . ? O3 C11 C10 105.7(3) . . ? C1 C11 C10 114.4(3) . . ? O3 C11 C18 89.1(3) . . ? C1 C11 C18 121.8(3) . . ? C10 C11 C18 108.2(3) . . ? O3 C12 C13 114.5(2) . . ? O3 C12 C9 105.7(2) . . ? C13 C12 C9 115.4(4) . . ? O3 C12 C18 89.3(3) . . ? C13 C12 C18 120.8(3) . . ? C9 C12 C18 107.6(3) . . ? C20A C13 C14 117.5(4) . . ? C20A C13 C12 116.8(4) . . ? C14 C13 C12 121.8(3) . . ? C20A C13 C20B 37.9(3) . . ? C14 C13 C20B 116.7(4) . . ? C12 C13 C20B 118.5(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16A C15 C14 119.4(4) . . ? C16A C15 C16B 26.5(4) . . ? C14 C15 C16B 119.3(4) . . ? C16A C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C16B C15 H15 113.7 . . ? C5 C17 C3 122.1(3) . . ? C5 C17 H17 119.0 . . ? C3 C17 H17 119.0 . . ? C12 C18 C11 83.3(3) . . ? C12 C18 H18A 114.7 . . ? C11 C18 H18A 114.7 . . ? C12 C18 H18B 114.7 . . ? C11 C18 H18B 114.7 . . ? H18A C18 H18B 111.8 . . ? C16A C19A C20A 121.6(7) . . ? C16A C19A H19A 119.2 . . ? C20A C19A H19A 119.2 . . ? C13 C20A C19A 116.0(6) . . ? C13 C20A H20A 122.0 . . ? C19A C20A H20A 122.0 . . ? C15 C16A C19A 120.3(6) . . ? C15 C16A H16A 119.9 . . ? C19A C16A H16A 119.9 . . ? C16B C19B C20B 121.3(6) . . ? C16B C19B H19B 119.3 . . ? C20B C19B H19B 119.3 . . ? C19B C20B C13 120.3(5) . . ? C19B C20B H20B 119.8 . . ? C13 C20B H20B 119.8 . . ? C19B C16B C15 118.1(5) . . ? C19B C16B H16B 120.9 . . ? C15 C16B H16B 120.9 . . ? C8 C21A H21A 109.5 . . ? C8 C21A H21B 109.5 . . ? C8 C21A H21C 109.5 . . ? C8 C22A H22A 109.5 . . ? C8 C22A H22B 109.5 . . ? C8 C22A H22C 109.5 . . ? C8 C23A H23A 109.5 . . ? C8 C23A H23B 109.5 . . ? C8 C23A H23C 109.5 . . ? C8 C21B H21D 109.5 . . ? C8 C21B H21E 109.5 . . ? C8 C21B H21F 109.5 . . ? C8 C22B H22D 109.5 . . ? C8 C22B H22E 109.5 . . ? C8 C22B H22F 109.5 . . ? C8 C23B H23D 109.5 . . ? C8 C23B H23E 109.5 . . ? C8 C23B H23F 109.5 . . ? C2 C24A H24A 109.5 . . ? C2 C24A H24B 109.5 . . ? C2 C24A H24C 109.5 . . ? C2 C25A H25A 109.5 . . ? C2 C25A H25B 109.5 . . ? C2 C25A H25C 109.5 . . ? C2 C26A H26A 109.5 . . ? C2 C26A H26B 109.5 . . ? C2 C26A H26C 109.5 . . ? C2 C24B H24D 109.5 . . ? C2 C24B H24E 109.5 . . ? C2 C24B H24F 109.5 . . ? C2 C25B H25D 109.5 . . ? C2 C25B H25E 109.5 . . ? C2 C25B H25F 109.5 . . ? C2 C26B H26D 109.5 . . ? C2 C26B H26E 109.5 . . ? C2 C26B H26F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 67.44 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.256 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.074 # start Validation Reply Form _vrf_PLAT230_ALERT_2_B ; PROBLEM: PLAT230_ALERT_2_B Hirshfeld Test Diff for ... RESPONSE: The problem, with the components of the anisotropic displacement parameters along chemical bonds, is due to the disorder observed for t-butyl groups. ; _database_code_depnum_ccdc_archive 'CCDC 942923' ####################################################################### # # 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_(S,S,P)_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H31 N O3' _chemical_formula_sum 'C26 H31 N O3' _chemical_formula_weight 405.52 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) _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4836(3) _cell_length_b 11.0788(3) _cell_length_c 11.5270(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.817(2) _cell_angle_gamma 90.00 _cell_volume 1159.31(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8394 _cell_measurement_theta_min 4.01 _cell_measurement_theta_max 68.00 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.594 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0875 _exptl_absorpt_correction_T_max 0.9512 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 16291 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 68.07 _reflns_number_total 4117 _reflns_number_gt 3957 _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^)+(0.0054P)^2^+0.8303P] 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 4117 _refine_ls_number_parameters 368 _refine_ls_number_restraints 441 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.181 _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 0.4293(2) 0.96509(16) 0.46294(17) 0.0392(5) Uani 1 1 d U B . O2 O 0.4372(2) 0.79802(16) 0.21281(15) 0.0394(5) Uani 1 1 d U . . O3 O 0.7810(3) 0.7193(2) 0.39435(19) 0.0762(9) Uani 1 1 d U C . N1 N 0.6167(3) 0.85425(18) 0.43021(18) 0.0292(5) Uani 1 1 d U B . C1 C 0.8208(4) 1.0619(3) 0.3935(3) 0.0451(8) Uani 1 1 d U . . C3 C 0.8428(4) 0.8964(3) 0.7473(2) 0.0438(8) Uani 1 1 d U C . C4 C 0.7389(3) 0.8590(2) 0.6427(2) 0.0313(6) Uani 1 1 d U C . H4 H 0.6714 0.7973 0.6479 0.038 Uiso 1 1 calc R . . C5 C 0.7298(3) 0.9086(2) 0.5300(2) 0.0288(5) Uani 1 1 d U . . C6 C 0.6552(4) 0.7538(2) 0.3708(2) 0.0428(8) Uani 1 1 d U . . C7 C 0.5251(4) 0.6968(2) 0.2791(2) 0.0459(8) Uani 1 1 d U B . C8 C 0.5631(5) 0.6035(3) 0.2003(3) 0.0576(10) Uani 1 1 d U . . C11 C 0.4046(4) 0.6738(2) 0.3425(3) 0.0531(9) Uani 1 1 d U . . H11A H 0.4422 0.6562 0.4303 0.064 Uiso 1 1 calc R B . H11B H 0.3272 0.6159 0.3003 0.064 Uiso 1 1 calc R . . C12 C 0.9390(4) 0.9858(3) 0.7322(3) 0.0505(8) Uani 1 1 d U C . H12 H 1.0133 1.0140 0.8012 0.061 Uiso 1 1 calc R . . C13 C 0.9301(4) 1.0350(3) 0.6201(3) 0.0439(7) Uani 1 1 d U . . H13 H 0.9994 1.0953 0.6150 0.053 Uiso 1 1 calc R C . C14 C 0.8240(3) 1.0000(2) 0.5141(2) 0.0342(6) Uani 1 1 d U C . C15 C 0.4692(3) 0.8850(2) 0.4082(2) 0.0331(6) Uani 1 1 d U . . C16 C 0.3670(3) 0.8078(3) 0.3111(2) 0.0387(7) Uani 1 1 d U B . C17 C 0.2124(4) 0.8509(3) 0.2707(3) 0.0569(9) Uani 1 1 d U . . H17A H 0.2094 0.9322 0.2364 0.085 Uiso 1 1 calc R B . H17B H 0.1723 0.8531 0.3400 0.085 Uiso 1 1 calc R . . H17C H 0.1534 0.7960 0.2089 0.085 Uiso 1 1 calc R . . C18 C 0.5706(4) 0.5324(3) 0.0061(3) 0.0484(8) Uani 1 1 d U . . H18 H 0.5323 0.5366 -0.0796 0.058 Uiso 1 1 calc R A 1 C19 C 0.5342(3) 0.6199(3) 0.0781(2) 0.0395(7) Uani 1 1 d U B . H19 H 0.4885 0.6924 0.0421 0.047 Uiso 1 1 calc R . . C20 C 0.8542(5) 0.8415(3) 0.8717(3) 0.0580(10) Uani 1 1 d U . . C9 C 0.6775(8) 0.5062(4) 0.2611(5) 0.0300(14) Uani 0.543(7) 1 d PU B 1 H9 H 0.7211 0.5070 0.3464 0.036 Uiso 0.543(7) 1 calc PR B 1 C23A C 0.7163(7) 0.4183(4) 0.1912(5) 0.0321(14) Uani 0.543(7) 1 d PU B 1 H23A H 0.7723 0.3507 0.2298 0.038 Uiso 0.543(7) 1 calc PR B 1 C10 C 0.6753(9) 0.4264(6) 0.0666(6) 0.0373(15) Uani 0.543(7) 1 d PU B 1 H10 H 0.7095 0.3697 0.0191 0.045 Uiso 0.543(7) 1 calc PR B 1 C9B C 0.5743(9) 0.4904(5) 0.2411(5) 0.0280(16) Uani 0.457(7) 1 d PU B 2 H9B H 0.5619 0.4703 0.3176 0.034 Uiso 0.457(7) 1 calc PR B 2 C23B C 0.6053(9) 0.4033(6) 0.1649(5) 0.040(2) Uani 0.457(7) 1 d PU B 2 H23B H 0.6337 0.3247 0.1959 0.048 Uiso 0.457(7) 1 calc PR B 2 C10B C 0.5961(9) 0.4276(7) 0.0467(6) 0.0310(16) Uani 0.457(7) 1 d PU B 2 H10B H 0.6091 0.3644 -0.0050 0.037 Uiso 0.457(7) 1 calc PR B 2 C24A C 0.9747(6) 1.0237(5) 0.3732(5) 0.0355(13) Uani 0.517(4) 1 d PU C 3 H24A H 0.9783 0.9358 0.3654 0.053 Uiso 0.517(4) 1 calc PR C 3 H24B H 1.0556 1.0503 0.4425 0.053 Uiso 0.517(4) 1 calc PR C 3 H24C H 0.9843 1.0617 0.2991 0.053 Uiso 0.517(4) 1 calc PR C 3 C25A C 0.7051(6) 1.0526(5) 0.2934(5) 0.0372(14) Uani 0.517(4) 1 d PU C 3 H25A H 0.7180 1.1088 0.2315 0.056 Uiso 0.517(4) 1 calc PR C 3 H25B H 0.6143 1.0725 0.3135 0.056 Uiso 0.517(4) 1 calc PR C 3 H25C H 0.6989 0.9699 0.2621 0.056 Uiso 0.517(4) 1 calc PR C 3 C26A C 0.8517(7) 1.2100(5) 0.4254(5) 0.0404(15) Uani 0.517(4) 1 d PU C 3 H26A H 0.8622 1.2522 0.3536 0.061 Uiso 0.517(4) 1 calc PR C 3 H26B H 0.9423 1.2195 0.4923 0.061 Uiso 0.517(4) 1 calc PR C 3 H26C H 0.7686 1.2443 0.4488 0.061 Uiso 0.517(4) 1 calc PR C 3 C24B C 0.7948(7) 0.9599(6) 0.2809(5) 0.0386(15) Uani 0.483(4) 1 d PU C 4 H24D H 0.6948 0.9270 0.2624 0.058 Uiso 0.483(4) 1 calc PR C 4 H24E H 0.8665 0.8943 0.3062 0.058 Uiso 0.483(4) 1 calc PR C 4 H24F H 0.8079 0.9990 0.2084 0.058 Uiso 0.483(4) 1 calc PR C 4 C25B C 0.6643(6) 1.1313(5) 0.3471(5) 0.0320(14) Uani 0.483(4) 1 d PU C 4 H25D H 0.6504 1.1608 0.2644 0.048 Uiso 0.483(4) 1 calc PR C 4 H25E H 0.6633 1.1996 0.4008 0.048 Uiso 0.483(4) 1 calc PR C 4 H25F H 0.5845 1.0753 0.3479 0.048 Uiso 0.483(4) 1 calc PR C 4 C26B C 0.9345(6) 1.1343(6) 0.3899(5) 0.0361(15) Uani 0.483(4) 1 d PU C 4 H26D H 0.9194 1.1637 0.3070 0.054 Uiso 0.483(4) 1 calc PR C 4 H26E H 1.0268 1.0886 0.4157 0.054 Uiso 0.483(4) 1 calc PR C 4 H26F H 0.9396 1.2031 0.4444 0.054 Uiso 0.483(4) 1 calc PR C 4 C2A C 1.0365(7) 0.7794(5) 0.9220(5) 0.0342(15) Uani 0.501(6) 1 d PU D 5 H2A1 H 1.0512 0.7406 1.0010 0.051 Uiso 0.501(6) 1 calc PR D 5 H2A2 H 1.1090 0.8441 0.9293 0.051 Uiso 0.501(6) 1 calc PR D 5 H2A3 H 1.0489 0.7195 0.8631 0.051 Uiso 0.501(6) 1 calc PR D 5 C22A C 0.7702(7) 0.7270(6) 0.8647(5) 0.0396(17) Uani 0.501(6) 1 d PU D 5 H22A H 0.8008 0.6699 0.8117 0.059 Uiso 0.501(6) 1 calc PR D 5 H22B H 0.6646 0.7435 0.8319 0.059 Uiso 0.501(6) 1 calc PR D 5 H22C H 0.7899 0.6922 0.9460 0.059 Uiso 0.501(6) 1 calc PR D 5 C21A C 0.8467(11) 0.9287(15) 0.9590(15) 0.039(2) Uani 0.501(6) 1 d PU D 5 H21A H 0.8660 0.8900 1.0385 0.059 Uiso 0.501(6) 1 calc PR D 5 H21B H 0.7483 0.9650 0.9365 0.059 Uiso 0.501(6) 1 calc PR D 5 H21C H 0.9206 0.9915 0.9626 0.059 Uiso 0.501(6) 1 calc PR D 5 C2B C 0.9251(10) 0.7424(6) 0.8950(6) 0.056(3) Uani 0.499(6) 1 d PU D 6 H2B1 H 1.0269 0.7553 0.8938 0.084 Uiso 0.499(6) 1 calc PR D 6 H2B2 H 0.8782 0.6821 0.8339 0.084 Uiso 0.499(6) 1 calc PR D 6 H2B3 H 0.9248 0.7137 0.9754 0.084 Uiso 0.499(6) 1 calc PR D 6 C22B C 0.6738(7) 0.8211(7) 0.8772(5) 0.054(2) Uani 0.499(6) 1 d PU D 6 H22D H 0.6241 0.7615 0.8161 0.081 Uiso 0.499(6) 1 calc PR D 6 H22E H 0.6208 0.8981 0.8606 0.081 Uiso 0.499(6) 1 calc PR D 6 H22F H 0.6751 0.7922 0.9578 0.081 Uiso 0.499(6) 1 calc PR D 6 C21B C 0.8994(11) 0.9417(14) 0.9711(15) 0.039(2) Uani 0.499(6) 1 d PU D 6 H21D H 0.8848 0.9118 1.0468 0.058 Uiso 0.499(6) 1 calc PR D 6 H21E H 0.8384 1.0135 0.9442 0.058 Uiso 0.499(6) 1 calc PR D 6 H21F H 1.0034 0.9625 0.9845 0.058 Uiso 0.499(6) 1 calc PR D 6 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 0.0476(12) 0.0312(10) 0.0366(10) -0.0045(8) 0.0085(9) 0.0092(9) O2 0.0698(14) 0.0234(9) 0.0212(8) 0.0040(7) 0.0069(9) -0.0059(9) O3 0.098(2) 0.0805(18) 0.0322(12) -0.0153(11) -0.0091(12) 0.0649(16) N1 0.0441(13) 0.0224(10) 0.0205(9) 0.0001(8) 0.0085(9) 0.0056(9) C1 0.072(2) 0.0365(16) 0.0377(16) 0.0125(13) 0.0337(16) 0.0178(15) C3 0.072(2) 0.0340(15) 0.0235(12) 0.0021(12) 0.0101(13) -0.0172(15) C4 0.0467(16) 0.0222(12) 0.0259(12) -0.0009(10) 0.0121(12) -0.0052(11) C5 0.0402(15) 0.0245(12) 0.0218(12) -0.0009(10) 0.0094(11) 0.0040(11) C6 0.077(2) 0.0290(14) 0.0176(12) 0.0019(11) 0.0060(13) 0.0192(15) C7 0.096(2) 0.0203(13) 0.0210(13) 0.0038(11) 0.0161(14) 0.0028(14) C8 0.126(3) 0.0197(13) 0.0300(15) -0.0031(12) 0.0266(18) -0.0027(16) C11 0.105(3) 0.0260(14) 0.0264(14) 0.0025(11) 0.0152(16) -0.0113(16) C12 0.071(2) 0.0451(18) 0.0311(15) -0.0005(13) 0.0075(15) -0.0267(16) C13 0.0547(19) 0.0375(16) 0.0402(15) 0.0076(13) 0.0147(14) -0.0143(14) C14 0.0452(16) 0.0294(13) 0.0316(13) 0.0055(11) 0.0169(12) 0.0050(12) C15 0.0500(17) 0.0236(13) 0.0213(12) 0.0053(10) 0.0033(11) 0.0020(12) C16 0.0565(18) 0.0307(14) 0.0251(13) 0.0052(11) 0.0060(12) -0.0062(13) C17 0.058(2) 0.065(2) 0.0407(17) 0.0054(16) 0.0037(16) -0.0113(17) C18 0.067(2) 0.0528(19) 0.0275(15) -0.0123(13) 0.0168(15) -0.0262(16) C19 0.0554(19) 0.0383(15) 0.0273(14) -0.0033(12) 0.0155(13) -0.0166(13) C20 0.096(3) 0.0494(19) 0.0227(14) 0.0042(13) 0.0075(16) -0.0349(18) C9 0.035(4) 0.025(2) 0.032(2) -0.0052(19) 0.014(2) -0.003(2) C23A 0.033(4) 0.026(2) 0.042(3) -0.003(2) 0.017(3) -0.001(2) C10 0.036(4) 0.035(3) 0.046(3) -0.016(2) 0.020(3) -0.019(3) C9B 0.031(4) 0.025(3) 0.023(3) -0.004(2) -0.001(2) 0.000(3) C23B 0.045(5) 0.026(3) 0.034(3) -0.005(2) -0.009(3) 0.016(3) C10B 0.023(4) 0.039(3) 0.027(3) -0.022(2) 0.001(3) -0.002(3) C24A 0.036(3) 0.039(3) 0.034(3) 0.007(2) 0.013(2) 0.000(2) C25A 0.051(3) 0.031(3) 0.033(3) 0.012(2) 0.018(2) 0.004(3) C26A 0.059(4) 0.030(3) 0.036(3) 0.006(2) 0.020(3) -0.003(3) C24B 0.053(4) 0.041(3) 0.028(3) -0.001(2) 0.022(3) 0.002(3) C25B 0.046(3) 0.029(3) 0.028(3) 0.005(2) 0.022(2) -0.006(2) C26B 0.036(3) 0.047(4) 0.027(3) 0.008(2) 0.011(2) 0.001(3) C2A 0.032(3) 0.040(3) 0.032(3) 0.008(2) 0.011(2) 0.007(3) C22A 0.036(4) 0.049(3) 0.034(3) 0.015(2) 0.010(3) -0.007(3) C21A 0.034(6) 0.053(5) 0.034(5) 0.008(3) 0.014(5) 0.001(5) C2B 0.091(7) 0.050(4) 0.042(4) 0.024(3) 0.042(4) 0.024(4) C22B 0.038(3) 0.093(6) 0.030(3) 0.020(3) 0.006(3) -0.014(3) C21B 0.046(7) 0.047(4) 0.025(4) 0.000(3) 0.013(6) -0.003(6) _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 C15 1.211(3) . ? O2 C7 1.473(3) . ? O2 C16 1.475(3) . ? O3 C6 1.206(4) . ? N1 C15 1.390(4) . ? N1 C6 1.409(3) . ? N1 C5 1.457(3) . ? C1 C25A 1.347(6) . ? C1 C26B 1.355(6) . ? C1 C14 1.543(3) . ? C1 C24A 1.601(6) . ? C1 C25B 1.618(6) . ? C1 C24B 1.685(6) . ? C1 C26A 1.689(6) . ? C3 C4 1.382(4) . ? C3 C12 1.392(4) . ? C3 C20 1.532(4) . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 C14 1.397(4) . ? C6 C7 1.511(4) . ? C7 C8 1.487(4) . ? C7 C11 1.546(5) . ? C8 C9B 1.332(6) . ? C8 C19 1.368(4) . ? C8 C9 1.546(7) . ? C11 C16 1.546(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.383(4) . ? C12 H12 0.9500 . ? C13 C14 1.394(4) . ? C13 H13 0.9500 . ? C15 C16 1.516(4) . ? C16 C17 1.483(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C10B 1.249(8) . ? C18 C19 1.382(4) . ? C18 C10 1.566(9) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C2B 1.274(7) . ? C20 C21A 1.412(15) . ? C20 C22A 1.487(6) . ? C20 C21B 1.564(13) . ? C20 C22B 1.745(7) . ? C20 C2A 1.794(7) . ? C9 C23A 1.381(7) . ? C9 H9 0.9500 . ? C23A C10 1.378(8) . ? C23A H23A 0.9500 . ? C10 H10 0.9500 . ? C9B C23B 1.392(8) . ? C9B H9B 0.9500 . ? C23B C10B 1.367(9) . ? C23B H23B 0.9500 . ? C10B H10B 0.9500 . ? C24A H24A 0.9800 . ? C24A H24B 0.9800 . ? C24A H24C 0.9800 . ? C25A H25A 0.9800 . ? C25A H25B 0.9800 . ? C25A H25C 0.9800 . ? C26A H26A 0.9800 . ? C26A H26B 0.9800 . ? C26A H26C 0.9800 . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? C25B H25D 0.9800 . ? C25B H25E 0.9800 . ? C25B H25F 0.9800 . ? C26B H26D 0.9800 . ? C26B H26E 0.9800 . ? C26B H26F 0.9800 . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 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 C7 O2 C16 88.34(19) . . ? C15 N1 C6 119.6(2) . . ? C15 N1 C5 121.0(2) . . ? C6 N1 C5 118.4(2) . . ? C25A C1 C26B 118.5(4) . . ? C25A C1 C14 122.5(3) . . ? C26B C1 C14 118.9(4) . . ? C25A C1 C24A 113.9(4) . . ? C26B C1 C24A 52.0(4) . . ? C14 C1 C24A 103.5(3) . . ? C25A C1 C25B 46.5(3) . . ? C26B C1 C25B 111.7(4) . . ? C14 C1 C25B 106.6(3) . . ? C24A C1 C25B 149.8(3) . . ? C25A C1 C24B 52.2(3) . . ? C26B C1 C24B 108.3(4) . . ? C14 C1 C24B 110.9(3) . . ? C24A C1 C24B 69.3(3) . . ? C25B C1 C24B 98.5(3) . . ? C25A C1 C26A 107.9(4) . . ? C26B C1 C26A 48.8(3) . . ? C14 C1 C26A 106.2(3) . . ? C24A C1 C26A 100.4(4) . . ? C25B C1 C26A 72.3(3) . . ? C24B C1 C26A 142.8(3) . . ? C4 C3 C12 115.6(2) . . ? C4 C3 C20 122.5(3) . . ? C12 C3 C20 121.9(3) . . ? C3 C4 C5 122.2(2) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C4 C5 C14 122.7(2) . . ? C4 C5 N1 114.0(2) . . ? C14 C5 N1 123.3(2) . . ? O3 C6 N1 121.3(3) . . ? O3 C6 C7 125.4(3) . . ? N1 C6 C7 113.3(3) . . ? O2 C7 C8 114.4(2) . . ? O2 C7 C6 105.7(2) . . ? C8 C7 C6 115.1(3) . . ? O2 C7 C11 89.2(2) . . ? C8 C7 C11 121.1(3) . . ? C6 C7 C11 107.7(2) . . ? C9B C8 C19 117.4(3) . . ? C9B C8 C7 116.6(3) . . ? C19 C8 C7 121.7(3) . . ? C9B C8 C9 37.8(3) . . ? C19 C8 C9 117.7(3) . . ? C7 C8 C9 118.0(3) . . ? C7 C11 C16 83.3(2) . . ? C7 C11 H11A 114.8 . . ? C16 C11 H11A 114.8 . . ? C7 C11 H11B 114.8 . . ? C16 C11 H11B 114.8 . . ? H11A C11 H11B 111.8 . . ? C13 C12 C3 122.2(3) . . ? C13 C12 H12 118.9 . . ? C3 C12 H12 118.9 . . ? C12 C13 C14 122.8(3) . . ? C12 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C13 C14 C5 114.5(2) . . ? C13 C14 C1 119.1(3) . . ? C5 C14 C1 126.4(3) . . ? O1 C15 N1 122.3(2) . . ? O1 C15 C16 124.7(3) . . ? N1 C15 C16 113.0(2) . . ? O2 C16 C17 114.0(2) . . ? O2 C16 C15 105.9(2) . . ? C17 C16 C15 114.4(3) . . ? O2 C16 C11 89.1(2) . . ? C17 C16 C11 121.6(3) . . ? C15 C16 C11 108.3(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C10B C18 C19 118.8(4) . . ? C10B C18 C10 26.7(3) . . ? C19 C18 C10 119.7(3) . . ? C10B C18 H18 114.1 . . ? C19 C18 H18 120.2 . . ? C10 C18 H18 120.2 . . ? C8 C19 C18 121.0(3) . . ? C8 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C2B C20 C21A 124.8(8) . . ? C2B C20 C22A 61.2(5) . . ? C21A C20 C22A 119.0(7) . . ? C2B C20 C3 115.5(4) . . ? C21A C20 C3 113.0(8) . . ? C22A C20 C3 113.3(3) . . ? C2B C20 C21B 116.2(7) . . ? C21A C20 C21B 18.5(6) . . ? C22A C20 C21B 132.4(6) . . ? C3 C20 C21B 109.5(7) . . ? C2B C20 C22B 110.1(5) . . ? C21A C20 C22B 79.1(5) . . ? C22A C20 C22B 51.4(4) . . ? C3 C20 C22B 106.3(3) . . ? C21B C20 C22B 97.4(5) . . ? C2B C20 C2A 37.0(5) . . ? C21A C20 C2A 106.0(6) . . ? C22A C20 C2A 98.1(4) . . ? C3 C20 C2A 104.8(3) . . ? C21B C20 C2A 90.1(5) . . ? C22B C20 C2A 143.3(4) . . ? C23A C9 C8 119.9(4) . . ? C23A C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C10 C23A C9 121.3(5) . . ? C10 C23A H23A 119.3 . . ? C9 C23A H23A 119.3 . . ? C23A C10 C18 117.7(5) . . ? C23A C10 H10 121.2 . . ? C18 C10 H10 121.2 . . ? C8 C9B C23B 116.1(5) . . ? C8 C9B H9B 122.0 . . ? C23B C9B H9B 122.0 . . ? C10B C23B C9B 121.9(6) . . ? C10B C23B H23B 119.1 . . ? C9B C23B H23B 119.1 . . ? C18 C10B C23B 120.4(6) . . ? C18 C10B H10B 119.8 . . ? C23B C10B H10B 119.8 . . ? C1 C24A H24A 109.5 . . ? C1 C24A H24B 109.5 . . ? C1 C24A H24C 109.5 . . ? C1 C25A H25A 109.5 . . ? C1 C25A H25B 109.5 . . ? C1 C25A H25C 109.5 . . ? C1 C26A H26A 109.5 . . ? C1 C26A H26B 109.5 . . ? C1 C26A H26C 109.5 . . ? C1 C24B H24D 109.5 . . ? C1 C24B H24E 109.5 . . ? C1 C24B H24F 109.5 . . ? C1 C25B H25D 109.5 . . ? C1 C25B H25E 109.5 . . ? C1 C25B H25F 109.5 . . ? C1 C26B H26D 109.5 . . ? C1 C26B H26E 109.5 . . ? C1 C26B H26F 109.5 . . ? C20 C2A H2A1 109.5 . . ? C20 C2A H2A2 109.5 . . ? C20 C2A H2A3 109.5 . . ? C20 C22A H22A 109.5 . . ? C20 C22A H22B 109.5 . . ? C20 C22A H22C 109.5 . . ? C20 C21A H21A 109.5 . . ? C20 C21A H21B 109.5 . . ? C20 C21A H21C 109.5 . . ? C20 C2B H2B1 109.5 . . ? C20 C2B H2B2 109.5 . . ? C20 C2B H2B3 109.5 . . ? C20 C22B H22D 109.5 . . ? C20 C22B H22E 109.5 . . ? C20 C22B H22F 109.5 . . ? C20 C21B H21D 109.5 . . ? C20 C21B H21E 109.5 . . ? C20 C21B H21F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 68.07 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.169 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 942924' ####################################################################### # # 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_(R,R,M)_2b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N O3' _chemical_formula_sum 'C23 H25 N O3' _chemical_formula_weight 363.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4687(3) _cell_length_b 8.4682(3) _cell_length_c 14.3425(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.349(2) _cell_angle_gamma 90.00 _cell_volume 1000.78(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7260 _cell_measurement_theta_min 5.37 _cell_measurement_theta_max 66.30 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max .24 _exptl_crystal_size_mid .17 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6715 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _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_reflns_number 9615 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.37 _diffrn_reflns_theta_max 66.60 _reflns_number_total 3355 _reflns_number_gt 3282 _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^)+(0.0544P)^2^+0.1286P] 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 0.04(16) _chemical_absolute_configuration ad _refine_ls_number_reflns 3355 _refine_ls_number_parameters 248 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.80070(12) 0.21834(12) 0.67588(7) 0.0249(2) Uani 1 1 d . . . O2 O 0.52955(13) 0.53111(12) 0.64975(8) 0.0310(3) Uani 1 1 d . . . O3 O 0.54203(13) 0.06189(13) 0.80665(8) 0.0313(3) Uani 1 1 d . . . C1 C 0.8917(2) 0.5630(2) 0.41344(13) 0.0370(4) Uani 1 1 d . . . H1 H 0.9436 0.6164 0.3723 0.044 Uiso 1 1 calc R . . C2 C 0.7819(2) 0.4449(2) 0.37845(12) 0.0325(3) Uani 1 1 d . . . H2 H 0.7575 0.4209 0.3134 0.039 Uiso 1 1 calc R . . C3 C 0.70737(18) 0.36128(19) 0.44023(11) 0.0276(3) Uani 1 1 d . . . H3 H 0.6343 0.2809 0.4166 0.033 Uiso 1 1 calc R . . C4 C 0.74261(18) 0.39836(18) 0.53727(10) 0.0253(3) Uani 1 1 d . . . C5 C 0.67421(18) 0.30374(17) 0.60652(10) 0.0248(3) Uani 1 1 d . . . C6 C 0.57795(18) 0.39787(18) 0.66658(10) 0.0253(3) Uani 1 1 d . . . N1 N 0.54943(15) 0.31028(15) 0.74380(9) 0.0253(3) Uani 1 1 d . . . C8 C 0.44586(18) 0.37252(17) 0.80312(11) 0.0262(3) Uani 1 1 d . . . C9 C 0.50801(18) 0.43542(18) 0.89423(11) 0.0269(3) Uani 1 1 d . . . C10 C 0.68963(18) 0.46688(19) 0.93843(10) 0.0283(3) Uani 1 1 d . . . C11 C 0.7180(2) 0.5157(3) 1.04373(12) 0.0427(4) Uani 1 1 d . . . H11A H 0.8315 0.5353 1.0689 0.064 Uiso 1 1 calc R . . H11B H 0.6829 0.4324 1.0796 0.064 Uiso 1 1 calc R . . H11C H 0.6575 0.6099 1.0487 0.064 Uiso 1 1 calc R . . C12 C 0.7456(2) 0.6041(2) 0.88401(13) 0.0366(4) Uani 1 1 d . . . H12A H 0.6811 0.6958 0.8883 0.055 Uiso 1 1 calc R . . H12B H 0.7331 0.5753 0.8180 0.055 Uiso 1 1 calc R . . H12C H 0.8576 0.6269 0.9117 0.055 Uiso 1 1 calc R . . C13 C 0.58575(18) 0.14675(18) 0.75047(10) 0.0255(3) Uani 1 1 d . . . C14 C 0.67963(19) 0.09385(17) 0.67726(10) 0.0264(3) Uani 1 1 d . . . C15 C 0.7525(2) -0.06876(18) 0.69384(11) 0.0303(3) Uani 1 1 d . . . H15A H 0.7901 -0.1011 0.6378 0.036 Uiso 1 1 calc R . . H15B H 0.6695 -0.1428 0.7023 0.036 Uiso 1 1 calc R . . C16 C 0.8939(2) -0.0750(2) 0.78148(12) 0.0360(4) Uani 1 1 d . . . H16A H 0.9718 0.0049 0.7761 0.054 Uiso 1 1 calc R . . H16B H 0.9444 -0.1770 0.7854 0.054 Uiso 1 1 calc R . . H16C H 0.8546 -0.0566 0.8382 0.054 Uiso 1 1 calc R . . C17 C 0.9247(2) 0.6023(2) 0.50999(13) 0.0389(4) Uani 1 1 d . . . H17 H 0.9974 0.6832 0.5332 0.047 Uiso 1 1 calc R . . C18 C 0.8498(2) 0.5214(2) 0.57181(12) 0.0335(3) Uani 1 1 d . . . H18 H 0.8710 0.5489 0.6363 0.040 Uiso 1 1 calc R . . C19 C 0.58352(19) 0.14728(17) 0.57707(10) 0.0263(3) Uani 1 1 d . . . H19A H 0.6126 0.0934 0.5237 0.032 Uiso 1 1 calc R . . H19B H 0.4669 0.1527 0.5696 0.032 Uiso 1 1 calc R . . C20 C 0.28087(19) 0.3585(2) 0.76408(11) 0.0317(3) Uani 1 1 d . . . H20 H 0.2448 0.3185 0.7024 0.038 Uiso 1 1 calc R . . C21 C 0.16912(19) 0.4033(2) 0.81582(12) 0.0347(4) Uani 1 1 d . . . H21 H 0.0583 0.3939 0.7898 0.042 Uiso 1 1 calc R . . C22 C 0.2265(2) 0.4624(2) 0.90711(13) 0.0365(4) Uani 1 1 d . . . H22 H 0.1536 0.4918 0.9435 0.044 Uiso 1 1 calc R . . C23 C 0.3914(2) 0.4784(2) 0.94498(11) 0.0328(3) Uani 1 1 d . . . H23 H 0.4264 0.5193 1.0065 0.039 Uiso 1 1 calc R . . C24 C 0.79710(19) 0.32215(19) 0.93456(13) 0.0340(4) Uani 1 1 d . . . H24A H 0.8048 0.3044 0.8696 0.051 Uiso 1 1 calc R . . H24B H 0.7502 0.2311 0.9575 0.051 Uiso 1 1 calc R . . H24C H 0.9035 0.3404 0.9741 0.051 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 0.0289(5) 0.0215(5) 0.0250(5) 0.0017(4) 0.0074(4) -0.0006(4) O2 0.0409(6) 0.0242(6) 0.0287(6) 0.0031(4) 0.0100(4) 0.0051(5) O3 0.0397(6) 0.0279(6) 0.0284(6) 0.0041(4) 0.0123(4) -0.0024(5) C1 0.0392(9) 0.0333(9) 0.0440(10) 0.0141(7) 0.0212(7) 0.0054(7) C2 0.0397(8) 0.0322(8) 0.0292(7) 0.0069(6) 0.0155(6) 0.0102(7) C3 0.0316(8) 0.0230(7) 0.0293(8) 0.0017(6) 0.0093(6) 0.0040(6) C4 0.0289(7) 0.0217(7) 0.0264(7) 0.0024(5) 0.0087(5) 0.0033(6) C5 0.0303(7) 0.0218(7) 0.0221(7) 0.0004(5) 0.0056(6) -0.0006(6) C6 0.0293(7) 0.0254(8) 0.0208(6) -0.0005(5) 0.0048(5) -0.0020(6) N1 0.0307(6) 0.0237(6) 0.0223(6) 0.0006(5) 0.0080(5) 0.0003(5) C8 0.0313(7) 0.0242(8) 0.0251(7) 0.0024(6) 0.0108(6) 0.0020(6) C9 0.0315(8) 0.0237(8) 0.0268(7) 0.0011(6) 0.0091(6) 0.0008(6) C10 0.0296(8) 0.0306(8) 0.0250(7) 0.0000(6) 0.0071(6) -0.0003(6) C11 0.0346(9) 0.0609(12) 0.0318(9) -0.0081(8) 0.0058(7) -0.0014(8) C12 0.0355(9) 0.0324(9) 0.0400(9) 0.0031(7) 0.0046(7) -0.0043(7) C13 0.0291(7) 0.0241(7) 0.0233(7) 0.0001(6) 0.0058(6) -0.0011(6) C14 0.0323(8) 0.0227(7) 0.0250(7) 0.0010(6) 0.0083(6) -0.0031(6) C15 0.0392(8) 0.0231(8) 0.0312(8) 0.0016(6) 0.0135(6) 0.0005(6) C16 0.0415(9) 0.0297(8) 0.0375(9) 0.0080(7) 0.0110(7) 0.0034(7) C17 0.0370(9) 0.0314(9) 0.0495(10) 0.0055(8) 0.0124(7) -0.0070(7) C18 0.0393(9) 0.0282(8) 0.0321(8) 0.0016(6) 0.0067(6) -0.0040(7) C19 0.0327(8) 0.0225(7) 0.0242(7) 0.0006(6) 0.0079(6) -0.0034(6) C20 0.0365(8) 0.0316(8) 0.0266(7) -0.0028(6) 0.0066(6) 0.0002(7) C21 0.0270(8) 0.0380(9) 0.0387(8) -0.0028(7) 0.0067(6) -0.0004(7) C22 0.0352(9) 0.0393(9) 0.0390(9) -0.0084(7) 0.0168(7) 0.0010(7) C23 0.0358(8) 0.0355(8) 0.0289(8) -0.0070(7) 0.0112(6) -0.0015(7) C24 0.0299(8) 0.0307(9) 0.0403(9) 0.0033(7) 0.0057(6) -0.0009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.4723(18) . ? O1 C14 1.4739(18) . ? O2 C6 1.206(2) . ? O3 C13 1.2002(19) . ? C1 C2 1.379(3) . ? C1 C17 1.388(3) . ? C1 H1 0.9300 . ? C2 C3 1.394(2) . ? C2 H2 0.9300 . ? C3 C4 1.390(2) . ? C3 H3 0.9300 . ? C4 C18 1.395(2) . ? C4 C5 1.493(2) . ? C5 C6 1.538(2) . ? C5 C19 1.541(2) . ? C6 N1 1.3995(19) . ? N1 C13 1.417(2) . ? N1 C8 1.4545(19) . ? C8 C20 1.385(2) . ? C8 C9 1.397(2) . ? C9 C23 1.403(2) . ? C9 C10 1.545(2) . ? C10 C11 1.530(2) . ? C10 C12 1.534(2) . ? C10 C24 1.535(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.523(2) . ? C14 C15 1.505(2) . ? C14 C19 1.547(2) . ? C15 C16 1.524(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.385(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.384(2) . ? C20 H20 0.9300 . ? C21 C22 1.381(3) . ? C21 H21 0.9300 . ? C22 C23 1.383(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 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 C5 O1 C14 87.74(10) . . ? C2 C1 C17 120.04(15) . . ? C2 C1 H1 120.0 . . ? C17 C1 H1 120.0 . . ? C1 C2 C3 120.22(15) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.84(15) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C18 119.71(14) . . ? C3 C4 C5 121.21(14) . . ? C18 C4 C5 119.01(13) . . ? O1 C5 C4 112.30(12) . . ? O1 C5 C6 105.85(11) . . ? C4 C5 C6 115.56(12) . . ? O1 C5 C19 90.10(11) . . ? C4 C5 C19 121.63(13) . . ? C6 C5 C19 107.71(12) . . ? O2 C6 N1 122.79(14) . . ? O2 C6 C5 124.92(14) . . ? N1 C6 C5 112.28(12) . . ? C6 N1 C13 119.79(12) . . ? C6 N1 C8 120.56(12) . . ? C13 N1 C8 117.74(12) . . ? C20 C8 C9 122.55(14) . . ? C20 C8 N1 114.88(13) . . ? C9 C8 N1 122.52(14) . . ? C8 C9 C23 115.21(14) . . ? C8 C9 C10 125.02(13) . . ? C23 C9 C10 119.70(13) . . ? C11 C10 C12 107.52(14) . . ? C11 C10 C24 106.97(14) . . ? C12 C10 C24 109.31(13) . . ? C11 C10 C9 111.47(13) . . ? C12 C10 C9 108.48(12) . . ? C24 C10 C9 112.94(13) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 N1 122.32(14) . . ? O3 C13 C14 125.29(14) . . ? N1 C13 C14 112.37(12) . . ? O1 C14 C15 113.29(12) . . ? O1 C14 C13 105.92(11) . . ? C15 C14 C13 114.85(12) . . ? O1 C14 C19 89.81(10) . . ? C15 C14 C19 121.54(13) . . ? C13 C14 C19 107.93(12) . . ? C14 C15 C16 112.17(13) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C1 120.22(16) . . ? C18 C17 H17 119.9 . . ? C1 C17 H17 119.9 . . ? C17 C18 C4 119.92(16) . . ? C17 C18 H18 120.0 . . ? C4 C18 H18 120.0 . . ? C5 C19 C14 82.81(11) . . ? C5 C19 H19A 114.8 . . ? C14 C19 H19A 114.8 . . ? C5 C19 H19B 114.8 . . ? C14 C19 H19B 114.8 . . ? H19A C19 H19B 111.9 . . ? C21 C20 C8 120.71(15) . . ? C21 C20 H20 119.6 . . ? C8 C20 H20 119.6 . . ? C22 C21 C20 118.25(15) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? C21 C22 C23 120.68(15) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C9 122.58(15) . . ? C22 C23 H23 118.7 . . ? C9 C23 H23 118.7 . . ? C10 C24 H24A 109.5 . . ? C10 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C10 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 66.60 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.145 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.030 _database_code_depnum_ccdc_archive 'CCDC 942925' ####################################################################### # # 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_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H31 N O3' _chemical_formula_sum 'C26 H31 N O3' _chemical_formula_weight 405.52 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 Triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7846(4) _cell_length_b 12.0025(6) _cell_length_c 20.5396(9) _cell_angle_alpha 89.213(2) _cell_angle_beta 76.836(2) _cell_angle_gamma 78.502(2) _cell_volume 2300.37(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9938 _cell_measurement_theta_min 4.75 _cell_measurement_theta_max 66.44 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6952 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 27607 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 66.58 _reflns_number_total 7861 _reflns_number_gt 6654 _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^)+(0.0447P)^2^+0.6237P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7861 _refine_ls_number_parameters 555 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O11 O 0.33635(11) -0.12304(8) 0.77841(5) 0.0287(2) Uani 1 1 d . . . O12 O 0.45679(10) 0.21233(8) 0.82067(5) 0.0223(2) Uani 1 1 d . . . O13 O 0.38554(10) -0.00924(8) 0.92116(4) 0.0206(2) Uani 1 1 d . . . O21 O -0.06912(10) 0.47567(8) 0.19314(4) 0.0216(2) Uani 1 1 d . . . O22 O 0.14473(10) 0.23576(8) 0.22736(5) 0.0274(2) Uani 1 1 d . . . O23 O -0.21844(10) 0.48638(8) 0.36160(4) 0.0243(2) Uani 1 1 d . . . N11 N 0.38852(11) 0.04995(9) 0.79536(5) 0.0167(2) Uani 1 1 d . . . N21 N -0.04192(11) 0.34686(9) 0.30134(5) 0.0177(2) Uani 1 1 d . . . C101 C 0.52549(14) 0.08871(12) 0.64360(6) 0.0215(3) Uani 1 1 d . . . C102 C 0.61959(15) 0.00069(13) 0.67777(7) 0.0289(3) Uani 1 1 d . . . H10A H 0.5739 -0.0649 0.6891 0.043 Uiso 1 1 calc R . . H10B H 0.6314 0.0349 0.7187 0.043 Uiso 1 1 calc R . . H10C H 0.7137 -0.0243 0.6474 0.043 Uiso 1 1 calc R . . C103 C 0.53040(16) 0.03598(14) 0.57517(7) 0.0301(3) Uani 1 1 d . . . H10D H 0.6304 0.0104 0.5511 0.045 Uiso 1 1 calc R . . H10E H 0.4813 0.0930 0.5491 0.045 Uiso 1 1 calc R . . H10F H 0.4826 -0.0291 0.5816 0.045 Uiso 1 1 calc R . . C104 C 0.59134(16) 0.19594(13) 0.63288(8) 0.0307(3) Uani 1 1 d . . . H10G H 0.5884 0.2300 0.6764 0.046 Uiso 1 1 calc R . . H10H H 0.5365 0.2509 0.6080 0.046 Uiso 1 1 calc R . . H10I H 0.6910 0.1750 0.6075 0.046 Uiso 1 1 calc R . . C105 C 0.36811(14) 0.12551(11) 0.68224(6) 0.0186(3) Uani 1 1 d . . . C106 C 0.27145(15) 0.19012(12) 0.64834(6) 0.0223(3) Uani 1 1 d . . . H106 H 0.3063 0.2053 0.6027 0.027 Uiso 1 1 calc R . . C107 C 0.12910(15) 0.23281(11) 0.67720(7) 0.0216(3) Uani 1 1 d . . . H107 H 0.0700 0.2761 0.6512 0.026 Uiso 1 1 calc R . . C108 C 0.07021(14) 0.21345(11) 0.74403(6) 0.0191(3) Uani 1 1 d . . . C109 C 0.16391(14) 0.14945(11) 0.77836(6) 0.0181(3) Uani 1 1 d . . . H109 H 0.1283 0.1335 0.8238 0.022 Uiso 1 1 calc R . . C110 C 0.30778(13) 0.10767(10) 0.74903(6) 0.0167(3) Uani 1 1 d . . . C111 C -0.08835(14) 0.25517(12) 0.77740(7) 0.0225(3) Uani 1 1 d . . . C112 C -0.16774(16) 0.16008(14) 0.77070(9) 0.0355(4) Uani 1 1 d . . . H11A H -0.1532 0.1392 0.7233 0.053 Uiso 1 1 calc R . . H11B H -0.2703 0.1864 0.7900 0.053 Uiso 1 1 calc R . . H11C H -0.1307 0.0936 0.7945 0.053 Uiso 1 1 calc R . . C113 C -0.15416(18) 0.36110(14) 0.74389(8) 0.0378(4) Uani 1 1 d . . . H11D H -0.1484 0.3423 0.6969 0.057 Uiso 1 1 calc R . . H11E H -0.1013 0.4217 0.7463 0.057 Uiso 1 1 calc R . . H11F H -0.2547 0.3870 0.7671 0.057 Uiso 1 1 calc R . . C114 C -0.10908(15) 0.28661(13) 0.85161(7) 0.0287(3) Uani 1 1 d . . . H11G H -0.2107 0.3175 0.8709 0.043 Uiso 1 1 calc R . . H11H H -0.0526 0.3438 0.8560 0.043 Uiso 1 1 calc R . . H11I H -0.0772 0.2185 0.8754 0.043 Uiso 1 1 calc R . . C116 C 0.44855(13) 0.11502(11) 0.83301(6) 0.0173(3) Uani 1 1 d . . . C117 C 0.38505(14) -0.06383(11) 0.81009(6) 0.0188(3) Uani 1 1 d . . . C118 C 0.50170(14) 0.04929(11) 0.88935(6) 0.0206(3) Uani 1 1 d . . . C119 C 0.54500(16) 0.12188(12) 0.93677(7) 0.0267(3) Uani 1 1 d . . . H11J H 0.4627 0.1813 0.9574 0.040 Uiso 1 1 calc R . . H11K H 0.6228 0.1572 0.9123 0.040 Uiso 1 1 calc R . . H11L H 0.5778 0.0746 0.9717 0.040 Uiso 1 1 calc R . . C120 C 0.59589(14) -0.06590(11) 0.86109(7) 0.0216(3) Uani 1 1 d . . . H12A H 0.6576 -0.1047 0.8901 0.026 Uiso 1 1 calc R . . H12B H 0.6496 -0.0654 0.8140 0.026 Uiso 1 1 calc R . . C121 C 0.45005(14) -0.10149(11) 0.87037(6) 0.0202(3) Uani 1 1 d . . . C122 C 0.43105(15) -0.21690(12) 0.89428(7) 0.0231(3) Uani 1 1 d . . . C123 C 0.30691(16) -0.23080(13) 0.93914(7) 0.0269(3) Uani 1 1 d . . . H123 H 0.2322 -0.1666 0.9541 0.032 Uiso 1 1 calc R . . C124 C 0.53875(18) -0.31094(14) 0.87242(9) 0.0411(4) Uani 1 1 d . . . H124 H 0.6242 -0.3026 0.8415 0.049 Uiso 1 1 calc R . . C125 C 0.5218(2) -0.41764(15) 0.89572(11) 0.0528(5) Uani 1 1 d . . . H125 H 0.5959 -0.4821 0.8805 0.063 Uiso 1 1 calc R . . C126 C 0.29056(19) -0.33748(14) 0.96236(7) 0.0339(4) Uani 1 1 d . . . H126 H 0.2051 -0.3463 0.9931 0.041 Uiso 1 1 calc R . . C127 C 0.3990(2) -0.43083(15) 0.94054(9) 0.0419(4) Uani 1 1 d . . . H127 H 0.3886 -0.5040 0.9565 0.050 Uiso 1 1 calc R . . C201 C 0.40492(16) 0.42953(14) 0.36824(7) 0.0309(3) Uani 1 1 d . . . H20A H 0.4526 0.3516 0.3527 0.046 Uiso 1 1 calc R . . H20B H 0.4761 0.4716 0.3762 0.046 Uiso 1 1 calc R . . H20C H 0.3580 0.4673 0.3342 0.046 Uiso 1 1 calc R . . C202 C 0.21013(17) 0.54781(12) 0.45565(8) 0.0307(3) Uani 1 1 d . . . H20D H 0.1582 0.5795 0.4219 0.046 Uiso 1 1 calc R . . H20E H 0.2780 0.5954 0.4606 0.046 Uiso 1 1 calc R . . H20F H 0.1418 0.5460 0.4986 0.046 Uiso 1 1 calc R . . C203 C 0.37022(15) 0.37798(12) 0.48782(7) 0.0258(3) Uani 1 1 d . . . H20G H 0.3007 0.3808 0.5308 0.039 Uiso 1 1 calc R . . H20H H 0.4412 0.4232 0.4916 0.039 Uiso 1 1 calc R . . H20I H 0.4186 0.2989 0.4757 0.039 Uiso 1 1 calc R . . C204 C 0.29212(14) 0.42650(11) 0.43360(7) 0.0216(3) Uani 1 1 d . . . C205 C 0.18675(14) 0.35405(11) 0.42251(6) 0.0189(3) Uani 1 1 d . . . C206 C 0.15460(14) 0.26401(11) 0.46211(6) 0.0210(3) Uani 1 1 d . . . H206 H 0.1992 0.2455 0.4985 0.025 Uiso 1 1 calc R . . C207 C 0.05875(14) 0.20025(11) 0.44987(7) 0.0215(3) Uani 1 1 d . . . H207 H 0.0402 0.1396 0.4785 0.026 Uiso 1 1 calc R . . C208 C -0.01181(14) 0.22060(11) 0.39762(6) 0.0187(3) Uani 1 1 d . . . C209 C 0.02105(13) 0.31268(11) 0.35821(6) 0.0179(3) Uani 1 1 d . . . C210 C 0.11611(14) 0.37665(11) 0.37046(6) 0.0188(3) Uani 1 1 d . . . H210 H 0.1340 0.4382 0.3424 0.023 Uiso 1 1 calc R . . C211 C -0.11680(14) 0.14611(11) 0.38715(7) 0.0221(3) Uani 1 1 d . . . C212 C -0.27009(16) 0.21667(13) 0.40311(9) 0.0343(4) Uani 1 1 d . . . H21A H -0.2755 0.2820 0.3740 0.051 Uiso 1 1 calc R . . H21B H -0.2965 0.2436 0.4500 0.051 Uiso 1 1 calc R . . H21C H -0.3363 0.1694 0.3955 0.051 Uiso 1 1 calc R . . C213 C -0.11375(16) 0.04494(12) 0.43375(8) 0.0292(3) Uani 1 1 d . . . H21D H -0.1808 -0.0012 0.4257 0.044 Uiso 1 1 calc R . . H21E H -0.1418 0.0731 0.4804 0.044 Uiso 1 1 calc R . . H21F H -0.0167 -0.0017 0.4249 0.044 Uiso 1 1 calc R . . C214 C -0.07821(17) 0.09496(12) 0.31563(7) 0.0292(3) Uani 1 1 d . . . H21G H -0.1034 0.1545 0.2848 0.044 Uiso 1 1 calc R . . H21H H -0.1314 0.0345 0.3137 0.044 Uiso 1 1 calc R . . H21I H 0.0249 0.0633 0.3027 0.044 Uiso 1 1 calc R . . C216 C -0.15901(13) 0.43895(11) 0.30829(6) 0.0180(3) Uani 1 1 d . . . C217 C -0.20297(14) 0.46862(11) 0.24236(6) 0.0194(3) Uani 1 1 d . . . C218 C -0.31791(15) 0.57167(11) 0.24581(7) 0.0238(3) Uani 1 1 d . . . H21J H -0.2871 0.6374 0.2613 0.036 Uiso 1 1 calc R . . H21K H -0.4054 0.5599 0.2771 0.036 Uiso 1 1 calc R . . H21L H -0.3371 0.5857 0.2013 0.036 Uiso 1 1 calc R . . C219 C -0.20778(14) 0.35736(11) 0.20739(6) 0.0204(3) Uani 1 1 d . . . H21M H -0.2620 0.3672 0.1718 0.025 Uiso 1 1 calc R . . H21N H -0.2337 0.2966 0.2380 0.025 Uiso 1 1 calc R . . C220 C -0.04515(14) 0.35203(11) 0.18274(7) 0.0214(3) Uani 1 1 d . . . C221 C 0.03245(14) 0.30322(11) 0.23714(6) 0.0201(3) Uani 1 1 d . . . C222 C 0.02919(15) 0.30963(13) 0.11300(7) 0.0265(3) Uani 1 1 d . . . C223 C 0.04687(17) 0.19532(14) 0.09604(8) 0.0354(4) Uani 1 1 d . . . H223 H 0.0177 0.1436 0.1293 0.043 Uiso 1 1 calc R . . C224 C 0.10749(19) 0.15645(17) 0.03024(9) 0.0462(5) Uani 1 1 d . . . H224 H 0.1203 0.0781 0.0186 0.055 Uiso 1 1 calc R . . C225 C 0.14911(18) 0.23168(19) -0.01818(8) 0.0485(5) Uani 1 1 d . . . H225 H 0.1892 0.2051 -0.0632 0.058 Uiso 1 1 calc R . . C226 C 0.1327(2) 0.34486(19) -0.00157(8) 0.0488(5) Uani 1 1 d . . . H226 H 0.1624 0.3962 -0.0349 0.059 Uiso 1 1 calc R . . C227 C 0.07264(18) 0.38441(16) 0.06433(8) 0.0378(4) Uani 1 1 d . . . H227 H 0.0615 0.4626 0.0758 0.045 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 O11 0.0381(6) 0.0237(5) 0.0321(5) 0.0046(4) -0.0191(5) -0.0123(4) O12 0.0250(5) 0.0190(5) 0.0255(5) 0.0023(4) -0.0105(4) -0.0052(4) O13 0.0210(5) 0.0233(5) 0.0176(4) 0.0015(4) -0.0045(4) -0.0051(4) O21 0.0219(5) 0.0221(5) 0.0208(5) 0.0015(4) -0.0035(4) -0.0060(4) O22 0.0210(5) 0.0322(5) 0.0255(5) -0.0045(4) -0.0063(4) 0.0045(4) O23 0.0267(5) 0.0237(5) 0.0201(5) -0.0039(4) -0.0052(4) 0.0010(4) N11 0.0165(5) 0.0184(5) 0.0159(5) 0.0017(4) -0.0057(4) -0.0032(4) N21 0.0178(5) 0.0188(5) 0.0171(5) -0.0008(4) -0.0058(4) -0.0025(4) C101 0.0202(7) 0.0275(7) 0.0175(6) -0.0011(5) -0.0028(5) -0.0081(5) C102 0.0205(7) 0.0375(8) 0.0239(7) -0.0006(6) -0.0004(6) -0.0002(6) C103 0.0276(8) 0.0420(9) 0.0204(7) -0.0063(6) -0.0014(6) -0.0103(6) C104 0.0239(7) 0.0341(8) 0.0340(8) -0.0013(6) -0.0005(6) -0.0125(6) C105 0.0196(7) 0.0212(7) 0.0173(6) -0.0004(5) -0.0058(5) -0.0076(5) C106 0.0256(7) 0.0282(7) 0.0164(6) 0.0060(5) -0.0073(5) -0.0110(6) C107 0.0227(7) 0.0239(7) 0.0226(7) 0.0061(5) -0.0125(5) -0.0068(5) C108 0.0188(7) 0.0194(6) 0.0217(6) 0.0007(5) -0.0079(5) -0.0063(5) C109 0.0199(7) 0.0202(6) 0.0155(6) 0.0020(5) -0.0051(5) -0.0065(5) C110 0.0186(6) 0.0175(6) 0.0168(6) 0.0023(5) -0.0081(5) -0.0054(5) C111 0.0185(7) 0.0246(7) 0.0249(7) 0.0006(5) -0.0074(5) -0.0029(5) C112 0.0190(7) 0.0401(9) 0.0467(9) -0.0107(7) -0.0025(6) -0.0089(6) C113 0.0296(8) 0.0410(9) 0.0369(9) 0.0095(7) -0.0085(7) 0.0070(7) C114 0.0211(7) 0.0347(8) 0.0277(7) -0.0024(6) -0.0047(6) -0.0003(6) C116 0.0124(6) 0.0216(7) 0.0169(6) -0.0013(5) -0.0028(5) -0.0013(5) C117 0.0162(6) 0.0204(6) 0.0193(6) 0.0018(5) -0.0035(5) -0.0031(5) C118 0.0194(7) 0.0247(7) 0.0193(6) 0.0034(5) -0.0068(5) -0.0060(5) C119 0.0311(8) 0.0309(8) 0.0238(7) 0.0042(6) -0.0145(6) -0.0100(6) C120 0.0188(7) 0.0231(7) 0.0237(7) 0.0048(5) -0.0080(5) -0.0027(5) C121 0.0190(7) 0.0219(7) 0.0192(6) 0.0010(5) -0.0048(5) -0.0024(5) C122 0.0246(7) 0.0248(7) 0.0233(7) 0.0067(5) -0.0118(6) -0.0063(6) C123 0.0314(8) 0.0307(8) 0.0222(7) 0.0006(6) -0.0086(6) -0.0117(6) C124 0.0291(9) 0.0273(8) 0.0614(11) 0.0122(7) -0.0032(8) -0.0018(7) C125 0.0399(10) 0.0266(9) 0.0888(15) 0.0155(9) -0.0153(10) 0.0004(7) C126 0.0455(9) 0.0429(9) 0.0230(7) 0.0090(6) -0.0135(7) -0.0256(8) C127 0.0511(11) 0.0337(9) 0.0539(10) 0.0233(8) -0.0292(9) -0.0205(8) C201 0.0236(8) 0.0462(9) 0.0275(8) 0.0069(7) -0.0079(6) -0.0159(7) C202 0.0356(8) 0.0245(7) 0.0369(8) 0.0009(6) -0.0151(7) -0.0096(6) C203 0.0251(7) 0.0298(8) 0.0273(7) 0.0023(6) -0.0119(6) -0.0103(6) C204 0.0201(7) 0.0247(7) 0.0224(7) 0.0023(5) -0.0069(5) -0.0077(5) C205 0.0163(6) 0.0210(6) 0.0184(6) -0.0019(5) -0.0032(5) -0.0023(5) C206 0.0204(7) 0.0237(7) 0.0200(6) 0.0018(5) -0.0074(5) -0.0035(5) C207 0.0225(7) 0.0202(7) 0.0224(7) 0.0045(5) -0.0057(5) -0.0054(5) C208 0.0160(6) 0.0180(6) 0.0211(6) -0.0020(5) -0.0037(5) -0.0012(5) C209 0.0164(6) 0.0197(6) 0.0169(6) -0.0015(5) -0.0051(5) -0.0001(5) C210 0.0191(6) 0.0184(6) 0.0185(6) 0.0022(5) -0.0037(5) -0.0037(5) C211 0.0201(7) 0.0202(7) 0.0281(7) 0.0011(5) -0.0089(5) -0.0054(5) C212 0.0204(7) 0.0277(8) 0.0565(10) 0.0009(7) -0.0097(7) -0.0078(6) C213 0.0314(8) 0.0280(8) 0.0343(8) 0.0072(6) -0.0124(6) -0.0149(6) C214 0.0396(9) 0.0218(7) 0.0322(8) 0.0020(6) -0.0169(7) -0.0106(6) C216 0.0175(6) 0.0161(6) 0.0214(7) 0.0004(5) -0.0052(5) -0.0048(5) C217 0.0193(7) 0.0198(7) 0.0198(6) 0.0017(5) -0.0049(5) -0.0053(5) C218 0.0248(7) 0.0213(7) 0.0254(7) 0.0018(5) -0.0084(6) -0.0017(5) C219 0.0199(7) 0.0207(7) 0.0218(7) -0.0009(5) -0.0079(5) -0.0030(5) C220 0.0210(7) 0.0225(7) 0.0208(7) -0.0024(5) -0.0062(5) -0.0026(5) C221 0.0193(7) 0.0208(7) 0.0207(7) -0.0022(5) -0.0053(5) -0.0044(5) C222 0.0191(7) 0.0382(8) 0.0220(7) -0.0058(6) -0.0080(5) -0.0010(6) C223 0.0315(8) 0.0413(9) 0.0307(8) -0.0114(7) -0.0130(7) 0.0069(7) C224 0.0363(10) 0.0562(11) 0.0411(10) -0.0252(9) -0.0178(8) 0.0146(8) C225 0.0287(9) 0.0852(15) 0.0247(8) -0.0196(9) -0.0055(7) 0.0053(9) C226 0.0370(10) 0.0833(15) 0.0238(8) -0.0026(9) -0.0008(7) -0.0134(9) C227 0.0332(9) 0.0553(11) 0.0251(8) -0.0021(7) -0.0030(6) -0.0134(8) _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 O11 C117 1.2019(16) . ? O12 C116 1.2063(16) . ? O13 C121 1.4716(16) . ? O13 C118 1.4764(16) . ? O21 C220 1.4662(16) . ? O21 C217 1.4775(16) . ? O22 C221 1.2051(16) . ? O23 C216 1.2067(16) . ? N11 C116 1.3998(16) . ? N11 C117 1.4001(17) . ? N11 C110 1.4545(15) . ? N21 C221 1.4046(17) . ? N21 C216 1.4071(17) . ? N21 C209 1.4582(16) . ? C101 C102 1.5305(19) . ? C101 C103 1.5362(18) . ? C101 C105 1.5421(18) . ? C101 C104 1.5421(19) . ? C102 H10A 0.9800 . ? C102 H10B 0.9800 . ? C102 H10C 0.9800 . ? C103 H10D 0.9800 . ? C103 H10E 0.9800 . ? C103 H10F 0.9800 . ? C104 H10G 0.9800 . ? C104 H10H 0.9800 . ? C104 H10I 0.9800 . ? C105 C110 1.3963(18) . ? C105 C106 1.4047(18) . ? C106 C107 1.379(2) . ? C106 H106 0.9500 . ? C107 C108 1.3981(19) . ? C107 H107 0.9500 . ? C108 C109 1.3881(18) . ? C108 C111 1.5307(18) . ? C109 C110 1.3917(19) . ? C109 H109 0.9500 . ? C111 C112 1.527(2) . ? C111 C114 1.5335(19) . ? C111 C113 1.5350(19) . ? C112 H11A 0.9800 . ? C112 H11B 0.9800 . ? C112 H11C 0.9800 . ? C113 H11D 0.9800 . ? C113 H11E 0.9800 . ? C113 H11F 0.9800 . ? C114 H11G 0.9800 . ? C114 H11H 0.9800 . ? C114 H11I 0.9800 . ? C116 C118 1.5222(17) . ? C117 C121 1.5396(17) . ? C118 C119 1.4985(19) . ? C118 C120 1.5389(19) . ? C118 C121 2.0386(19) . ? C119 H11J 0.9800 . ? C119 H11K 0.9800 . ? C119 H11L 0.9800 . ? C120 C121 1.5401(18) . ? C120 H12A 0.9900 . ? C120 H12B 0.9900 . ? C121 C122 1.4957(19) . ? C122 C124 1.382(2) . ? C122 C123 1.385(2) . ? C123 C126 1.387(2) . ? C123 H123 0.9500 . ? C124 C125 1.389(2) . ? C124 H124 0.9500 . ? C125 C127 1.373(3) . ? C125 H125 0.9500 . ? C126 C127 1.380(3) . ? C126 H126 0.9500 . ? C127 H127 0.9500 . ? C201 C204 1.5368(19) . ? C201 H20A 0.9800 . ? C201 H20B 0.9800 . ? C201 H20C 0.9800 . ? C202 C204 1.535(2) . ? C202 H20D 0.9800 . ? C202 H20E 0.9800 . ? C202 H20F 0.9800 . ? C203 C204 1.5348(18) . ? C203 H20G 0.9800 . ? C203 H20H 0.9800 . ? C203 H20I 0.9800 . ? C204 C205 1.5300(18) . ? C205 C206 1.3869(19) . ? C205 C210 1.3958(18) . ? C206 C207 1.3883(19) . ? C206 H206 0.9500 . ? C207 C208 1.3968(18) . ? C207 H207 0.9500 . ? C208 C209 1.4066(18) . ? C208 C211 1.5404(18) . ? C209 C210 1.3837(18) . ? C210 H210 0.9500 . ? C211 C212 1.533(2) . ? C211 C214 1.535(2) . ? C211 C213 1.5356(19) . ? C212 H21A 0.9800 . ? C212 H21B 0.9800 . ? C212 H21C 0.9800 . ? C213 H21D 0.9800 . ? C213 H21E 0.9800 . ? C213 H21F 0.9800 . ? C214 H21G 0.9800 . ? C214 H21H 0.9800 . ? C214 H21I 0.9800 . ? C216 C217 1.5286(17) . ? C217 C218 1.4870(18) . ? C217 C219 1.5389(18) . ? C218 H21J 0.9800 . ? C218 H21K 0.9800 . ? C218 H21L 0.9800 . ? C219 C220 1.5446(19) . ? C219 H21M 0.9900 . ? C219 H21N 0.9900 . ? C220 C222 1.4959(19) . ? C220 C221 1.5360(18) . ? C222 C227 1.385(2) . ? C222 C223 1.387(2) . ? C223 C224 1.392(2) . ? C223 H223 0.9500 . ? C224 C225 1.381(3) . ? C224 H224 0.9500 . ? C225 C226 1.374(3) . ? C225 H225 0.9500 . ? C226 C227 1.395(2) . ? C226 H226 0.9500 . ? C227 H227 0.9500 . ? 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 C121 O13 C118 87.50(9) . . ? C220 O21 C217 87.80(9) . . ? C116 N11 C117 120.48(10) . . ? C116 N11 C110 118.46(10) . . ? C117 N11 C110 120.17(10) . . ? C221 N21 C216 119.54(10) . . ? C221 N21 C209 119.02(10) . . ? C216 N21 C209 120.16(10) . . ? C102 C101 C103 106.62(12) . . ? C102 C101 C105 115.31(11) . . ? C103 C101 C105 109.33(11) . . ? C102 C101 C104 108.47(12) . . ? C103 C101 C104 109.09(11) . . ? C105 C101 C104 107.89(11) . . ? C101 C102 H10A 109.5 . . ? C101 C102 H10B 109.5 . . ? H10A C102 H10B 109.5 . . ? C101 C102 H10C 109.5 . . ? H10A C102 H10C 109.5 . . ? H10B C102 H10C 109.5 . . ? C101 C103 H10D 109.5 . . ? C101 C103 H10E 109.5 . . ? H10D C103 H10E 109.5 . . ? C101 C103 H10F 109.5 . . ? H10D C103 H10F 109.5 . . ? H10E C103 H10F 109.5 . . ? C101 C104 H10G 109.5 . . ? C101 C104 H10H 109.5 . . ? H10G C104 H10H 109.5 . . ? C101 C104 H10I 109.5 . . ? H10G C104 H10I 109.5 . . ? H10H C104 H10I 109.5 . . ? C110 C105 C106 114.04(12) . . ? C110 C105 C101 128.32(12) . . ? C106 C105 C101 117.57(11) . . ? C107 C106 C105 124.06(12) . . ? C107 C106 H106 118.0 . . ? C105 C106 H106 118.0 . . ? C106 C107 C108 121.15(12) . . ? C106 C107 H107 119.4 . . ? C108 C107 H107 119.4 . . ? C109 C108 C107 115.69(12) . . ? C109 C108 C111 121.28(12) . . ? C107 C108 C111 122.98(11) . . ? C108 C109 C110 122.77(12) . . ? C108 C109 H109 118.6 . . ? C110 C109 H109 118.6 . . ? C109 C110 C105 122.29(11) . . ? C109 C110 N11 113.54(11) . . ? C105 C110 N11 124.09(11) . . ? C112 C111 C108 108.21(11) . . ? C112 C111 C114 109.53(12) . . ? C108 C111 C114 111.37(11) . . ? C112 C111 C113 108.83(13) . . ? C108 C111 C113 111.38(12) . . ? C114 C111 C113 107.49(12) . . ? C111 C112 H11A 109.5 . . ? C111 C112 H11B 109.5 . . ? H11A C112 H11B 109.5 . . ? C111 C112 H11C 109.5 . . ? H11A C112 H11C 109.5 . . ? H11B C112 H11C 109.5 . . ? C111 C113 H11D 109.5 . . ? C111 C113 H11E 109.5 . . ? H11D C113 H11E 109.5 . . ? C111 C113 H11F 109.5 . . ? H11D C113 H11F 109.5 . . ? H11E C113 H11F 109.5 . . ? C111 C114 H11G 109.5 . . ? C111 C114 H11H 109.5 . . ? H11G C114 H11H 109.5 . . ? C111 C114 H11I 109.5 . . ? H11G C114 H11I 109.5 . . ? H11H C114 H11I 109.5 . . ? O12 C116 N11 122.32(11) . . ? O12 C116 C118 124.95(11) . . ? N11 C116 C118 112.73(11) . . ? O11 C117 N11 122.57(11) . . ? O11 C117 C121 125.37(12) . . ? N11 C117 C121 112.06(11) . . ? O13 C118 C119 114.13(11) . . ? O13 C118 C116 105.08(10) . . ? C119 C118 C116 113.62(11) . . ? O13 C118 C120 89.77(10) . . ? C119 C118 C120 121.74(11) . . ? C116 C118 C120 109.15(10) . . ? O13 C118 C121 46.15(6) . . ? C119 C118 C121 147.96(10) . . ? C116 C118 C121 97.44(9) . . ? C120 C118 C121 48.56(7) . . ? C118 C119 H11J 109.5 . . ? C118 C119 H11K 109.5 . . ? H11J C119 H11K 109.5 . . ? C118 C119 H11L 109.5 . . ? H11J C119 H11L 109.5 . . ? H11K C119 H11L 109.5 . . ? C118 C120 C121 82.92(10) . . ? C118 C120 H12A 114.8 . . ? C121 C120 H12A 114.8 . . ? C118 C120 H12B 114.8 . . ? C121 C120 H12B 114.8 . . ? H12A C120 H12B 111.9 . . ? O13 C121 C122 114.08(10) . . ? O13 C121 C117 104.64(10) . . ? C122 C121 C117 114.34(11) . . ? O13 C121 C120 89.90(10) . . ? C122 C121 C120 120.99(11) . . ? C117 C121 C120 109.39(10) . . ? O13 C121 C118 46.35(6) . . ? C122 C121 C118 147.49(10) . . ? C117 C121 C118 97.27(9) . . ? C120 C121 C118 48.51(7) . . ? C124 C122 C123 119.23(14) . . ? C124 C122 C121 120.07(13) . . ? C123 C122 C121 120.69(13) . . ? C122 C123 C126 120.68(14) . . ? C122 C123 H123 119.7 . . ? C126 C123 H123 119.7 . . ? C122 C124 C125 119.89(16) . . ? C122 C124 H124 120.1 . . ? C125 C124 H124 120.1 . . ? C127 C125 C124 120.65(17) . . ? C127 C125 H125 119.7 . . ? C124 C125 H125 119.7 . . ? C127 C126 C123 119.70(15) . . ? C127 C126 H126 120.2 . . ? C123 C126 H126 120.2 . . ? C125 C127 C126 119.86(15) . . ? C125 C127 H127 120.1 . . ? C126 C127 H127 120.1 . . ? C204 C201 H20A 109.5 . . ? C204 C201 H20B 109.5 . . ? H20A C201 H20B 109.5 . . ? C204 C201 H20C 109.5 . . ? H20A C201 H20C 109.5 . . ? H20B C201 H20C 109.5 . . ? C204 C202 H20D 109.5 . . ? C204 C202 H20E 109.5 . . ? H20D C202 H20E 109.5 . . ? C204 C202 H20F 109.5 . . ? H20D C202 H20F 109.5 . . ? H20E C202 H20F 109.5 . . ? C204 C203 H20G 109.5 . . ? C204 C203 H20H 109.5 . . ? H20G C203 H20H 109.5 . . ? C204 C203 H20I 109.5 . . ? H20G C203 H20I 109.5 . . ? H20H C203 H20I 109.5 . . ? C205 C204 C202 109.32(11) . . ? C205 C204 C203 111.50(11) . . ? C202 C204 C203 108.51(11) . . ? C205 C204 C201 109.59(11) . . ? C202 C204 C201 109.66(12) . . ? C203 C204 C201 108.23(11) . . ? C206 C205 C210 115.91(12) . . ? C206 C205 C204 123.61(11) . . ? C210 C205 C204 120.48(11) . . ? C205 C206 C207 121.54(12) . . ? C205 C206 H206 119.2 . . ? C207 C206 H206 119.2 . . ? C206 C207 C208 123.47(12) . . ? C206 C207 H207 118.3 . . ? C208 C207 H207 118.3 . . ? C207 C208 C209 114.34(12) . . ? C207 C208 C211 120.50(11) . . ? C209 C208 C211 125.16(11) . . ? C210 C209 C208 122.31(11) . . ? C210 C209 N21 115.35(11) . . ? C208 C209 N21 122.34(11) . . ? C209 C210 C205 122.42(12) . . ? C209 C210 H210 118.8 . . ? C205 C210 H210 118.8 . . ? C212 C211 C214 110.13(12) . . ? C212 C211 C213 107.56(12) . . ? C214 C211 C213 106.15(11) . . ? C212 C211 C208 109.72(11) . . ? C214 C211 C208 111.85(11) . . ? C213 C211 C208 111.29(11) . . ? C211 C212 H21A 109.5 . . ? C211 C212 H21B 109.5 . . ? H21A C212 H21B 109.5 . . ? C211 C212 H21C 109.5 . . ? H21A C212 H21C 109.5 . . ? H21B C212 H21C 109.5 . . ? C211 C213 H21D 109.5 . . ? C211 C213 H21E 109.5 . . ? H21D C213 H21E 109.5 . . ? C211 C213 H21F 109.5 . . ? H21D C213 H21F 109.5 . . ? H21E C213 H21F 109.5 . . ? C211 C214 H21G 109.5 . . ? C211 C214 H21H 109.5 . . ? H21G C214 H21H 109.5 . . ? C211 C214 H21I 109.5 . . ? H21G C214 H21I 109.5 . . ? H21H C214 H21I 109.5 . . ? O23 C216 N21 122.28(11) . . ? O23 C216 C217 124.82(12) . . ? N21 C216 C217 112.89(11) . . ? O21 C217 C218 113.41(11) . . ? O21 C217 C216 105.67(10) . . ? C218 C217 C216 114.97(11) . . ? O21 C217 C219 89.58(9) . . ? C218 C217 C219 121.39(11) . . ? C216 C217 C219 108.20(10) . . ? C217 C218 H21J 109.5 . . ? C217 C218 H21K 109.5 . . ? H21J C218 H21K 109.5 . . ? C217 C218 H21L 109.5 . . ? H21J C218 H21L 109.5 . . ? H21K C218 H21L 109.5 . . ? C217 C219 C220 82.90(10) . . ? C217 C219 H21M 114.8 . . ? C220 C219 H21M 114.8 . . ? C217 C219 H21N 114.8 . . ? C220 C219 H21N 114.8 . . ? H21M C219 H21N 111.9 . . ? O21 C220 C222 114.57(11) . . ? O21 C220 C221 104.36(10) . . ? C222 C220 C221 114.99(11) . . ? O21 C220 C219 89.78(9) . . ? C222 C220 C219 119.75(11) . . ? C221 C220 C219 109.83(11) . . ? O22 C221 N21 122.49(12) . . ? O22 C221 C220 125.21(12) . . ? N21 C221 C220 112.30(11) . . ? C227 C222 C223 119.74(14) . . ? C227 C222 C220 120.64(14) . . ? C223 C222 C220 119.50(14) . . ? C222 C223 C224 119.89(17) . . ? C222 C223 H223 120.1 . . ? C224 C223 H223 120.1 . . ? C225 C224 C223 120.07(18) . . ? C225 C224 H224 120.0 . . ? C223 C224 H224 120.0 . . ? C226 C225 C224 120.27(15) . . ? C226 C225 H225 119.9 . . ? C224 C225 H225 119.9 . . ? C225 C226 C227 120.01(18) . . ? C225 C226 H226 120.0 . . ? C227 C226 H226 120.0 . . ? C222 C227 C226 120.01(17) . . ? C222 C227 H227 120.0 . . ? C226 C227 H227 120.0 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.241 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 942926' ####################################################################### # # 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_2c _chemical_melting_point ? _chemical_formula_moiety 'C31 H33 N O3' _chemical_formula_sum 'C31 H33 N O3' _chemical_formula_weight 467.58 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 Monoclinic _symmetry_space_group_name_H-M Cc _space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.5834(4) _cell_length_b 22.5492(7) _cell_length_c 11.4549(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.314(2) _cell_angle_gamma 90.00 _cell_volume 2582.89(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7992 _cell_measurement_theta_min 3.92 _cell_measurement_theta_max 66.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6121 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 18163 _diffrn_reflns_av_R_equivalents 0.1111 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 66.65 _reflns_number_total 3923 _reflns_number_gt 3087 _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^)+(0.1049P)^2^+6.6743P] 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 0.0014(3) _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 -0.5(5) _refine_ls_number_reflns 3923 _refine_ls_number_parameters 332 _refine_ls_number_restraints 363 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2325 _refine_ls_wR_factor_gt 0.1774 _refine_ls_goodness_of_fit_ref 1.188 _refine_ls_restrained_S_all 1.140 _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 0.2441(4) 0.00051(14) 0.9702(3) 0.0355(9) Uani 1 1 d U . . O2 O 0.0231(5) 0.09755(16) 0.7233(4) 0.0449(11) Uani 1 1 d U . . O3 O 0.4723(4) 0.07962(14) 0.9215(4) 0.0403(10) Uani 1 1 d U . . N1 N 0.2525(5) 0.09692(15) 0.8430(4) 0.0333(11) Uani 1 1 d U . . C1 C 0.5003(6) -0.0475(2) 1.1433(5) 0.0390(14) Uani 1 1 d U . . H1TE H 0.4474 -0.0327 1.1788 0.047 Uiso 1 1 calc R . . C2 C 0.6194(7) -0.0791(2) 1.2279(6) 0.0470(16) Uani 1 1 d U . . H5ST H 0.6492 -0.0841 1.3213 0.056 Uiso 1 1 calc R . . C3 C 0.6906(7) -0.1020(2) 1.1739(6) 0.0485(15) Uani 1 1 d U . . H7DQ H 0.7693 -0.1243 1.2292 0.058 Uiso 1 1 calc R . . C4 C 0.6499(7) -0.0933(2) 1.0405(7) 0.0502(16) Uani 1 1 d U . . H7SN H 0.7014 -0.1091 1.0045 0.060 Uiso 1 1 calc R . . C5 C 0.5357(7) -0.0620(2) 0.9580(6) 0.0441(15) Uani 1 1 d U . . H2SB H 0.5083 -0.0567 0.8652 0.053 Uiso 1 1 calc R . . C6 C 0.4606(6) -0.03823(19) 1.0091(5) 0.0329(11) Uani 1 1 d U . . C7 C 0.3366(6) -0.0031(2) 0.9203(5) 0.0336(11) Uani 1 1 d U . . C8 C 0.2239(6) -0.0269(2) 0.7837(5) 0.0340(12) Uani 1 1 d U . . H3EA H 0.2207 -0.0092 0.7030 0.041 Uiso 1 1 calc R . . H3EB H 0.2158 -0.0706 0.7773 0.041 Uiso 1 1 calc R . . C9 C 0.1351(6) 0.0040(2) 0.8295(5) 0.0365(11) Uani 1 1 d U . . C10 C 0.0061(6) -0.0230(2) 0.8019(5) 0.0357(12) Uani 1 1 d U . . C11 C -0.0042(7) -0.0440(2) 0.9099(6) 0.0448(15) Uani 1 1 d U . . H1ND H 0.0700 -0.0414 0.9993 0.054 Uiso 1 1 calc R . . C12 C -0.1252(8) -0.0690(3) 0.8859(7) 0.0547(17) Uani 1 1 d U . . H0LO H -0.1331 -0.0837 0.9593 0.066 Uiso 1 1 calc R . . C13 C -0.2328(8) -0.0723(2) 0.7557(7) 0.0492(15) Uani 1 1 d U . . H0DC H -0.3155 -0.0881 0.7399 0.059 Uiso 1 1 calc R . . C14 C -0.2205(7) -0.0529(3) 0.6494(6) 0.0515(17) Uani 1 1 d U . . H8MD H -0.2940 -0.0561 0.5598 0.062 Uiso 1 1 calc R . . C15 C -0.0999(7) -0.0284(2) 0.6726(6) 0.0497(16) Uani 1 1 d U . . H8QQ H -0.0913 -0.0154 0.5984 0.060 Uiso 1 1 calc R . . C16 C 0.3620(7) 0.0606(2) 0.8968(5) 0.0368(13) Uani 1 1 d U . . C17 C 0.1235(7) 0.0700(2) 0.7903(5) 0.0394(13) Uani 1 1 d U . . C18 C 0.2624(6) 0.1587(2) 0.8111(5) 0.0315(13) Uani 1 1 d U . . C19 C 0.2516(6) 0.1672(2) 0.6860(5) 0.0326(12) Uani 1 1 d U . . H8OL H 0.2367 0.1339 0.6293 0.039 Uiso 1 1 calc R . . C20 C 0.2617(6) 0.2230(2) 0.6418(5) 0.0363(13) Uani 1 1 d U A . C21 C 0.2842(6) 0.2695(2) 0.7308(5) 0.0392(14) Uani 1 1 d U . . H3WJ H 0.2930 0.3086 0.7055 0.047 Uiso 1 1 calc R . . C22 C 0.2939(7) 0.2606(2) 0.8536(5) 0.0426(15) Uani 1 1 d U . . H5HK H 0.3090 0.2940 0.9100 0.051 Uiso 1 1 calc R . . C23 C 0.2827(6) 0.2045(2) 0.9008(5) 0.0380(14) Uani 1 1 d U . . C24 C 0.2929(8) 0.1973(2) 1.0390(6) 0.0476(16) Uani 1 1 d U . . C25 C 0.1700(10) 0.1648(4) 1.0267(8) 0.071(2) Uani 1 1 d U . . H5BA H 0.1717 0.1672 1.1129 0.106 Uiso 1 1 calc R . . H5BB H 0.1721 0.1231 1.0037 0.106 Uiso 1 1 calc R . . H5BC H 0.0881 0.1834 0.9555 0.106 Uiso 1 1 calc R . . C26 C 0.2994(13) 0.2570(3) 1.1040(8) 0.096(3) Uani 1 1 d U . . H0WA H 0.3835 0.2769 1.1271 0.143 Uiso 1 1 calc R . . H0WB H 0.2949 0.2509 1.1863 0.143 Uiso 1 1 calc R . . H0WC H 0.2240 0.2817 1.0405 0.143 Uiso 1 1 calc R . . C27 C 0.4159(9) 0.1613(3) 1.1350(6) 0.066(2) Uani 1 1 d U . . H3GA H 0.4957 0.1798 1.1421 0.099 Uiso 1 1 calc R . . H3GB H 0.4068 0.1208 1.1001 0.099 Uiso 1 1 calc R . . H3GC H 0.4243 0.1600 1.2245 0.099 Uiso 1 1 calc R . . C28 C 0.2530(7) 0.2337(3) 0.5063(5) 0.0426(14) Uani 1 1 d U . . C29 C 0.1639(10) 0.2862(3) 0.4342(7) 0.076(3) Uani 1 1 d U A . H4KA H 0.0756 0.2798 0.4240 0.113 Uiso 1 1 calc R . . H4KB H 0.1546 0.2905 0.3447 0.113 Uiso 1 1 calc R . . H4KC H 0.2037 0.3223 0.4872 0.113 Uiso 1 1 calc R . . C30 C 0.3944(15) 0.2515(16) 0.5345(14) 0.089(7) Uani 0.76(5) 1 d PU A 1 H1A1 H 0.4572 0.2190 0.5819 0.134 Uiso 0.76(5) 1 calc PR A 1 H1A2 H 0.4242 0.2872 0.5908 0.134 Uiso 0.76(5) 1 calc PR A 1 H1A3 H 0.3909 0.2593 0.4487 0.134 Uiso 0.76(5) 1 calc PR A 1 C31 C 0.391(5) 0.214(3) 0.523(6) 0.078(9) Uani 0.24(5) 1 d PU A 2 H1B1 H 0.4203 0.1770 0.5749 0.117 Uiso 0.24(5) 1 calc PR A 2 H1B2 H 0.4582 0.2450 0.5720 0.117 Uiso 0.24(5) 1 calc PR A 2 H1B3 H 0.3815 0.2081 0.4342 0.117 Uiso 0.24(5) 1 calc PR A 2 C32 C 0.1936(11) 0.1813(3) 0.4126(7) 0.074(2) Uani 1 1 d U A . H32A H 0.1037 0.1733 0.3969 0.111 Uiso 1 1 calc R . . H32B H 0.2503 0.1463 0.4537 0.111 Uiso 1 1 calc R . . H32C H 0.1884 0.1900 0.3262 0.111 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 0.052(3) 0.0302(17) 0.0266(17) 0.0019(13) 0.0213(17) 0.0011(16) O2 0.064(3) 0.0309(19) 0.044(2) 0.0128(16) 0.030(2) 0.0080(19) O3 0.058(3) 0.0257(16) 0.040(2) 0.0061(15) 0.027(2) 0.0005(17) N1 0.057(3) 0.0164(17) 0.028(2) 0.0027(15) 0.022(2) -0.0020(18) C1 0.057(4) 0.031(3) 0.033(3) 0.004(2) 0.026(3) 0.011(2) C2 0.063(5) 0.040(3) 0.035(3) 0.011(2) 0.023(3) 0.013(3) C3 0.055(4) 0.038(3) 0.050(3) 0.015(3) 0.025(3) 0.011(3) C4 0.068(5) 0.037(3) 0.067(4) 0.018(3) 0.050(4) 0.015(3) C5 0.071(5) 0.032(2) 0.041(3) 0.013(2) 0.037(3) 0.015(3) C6 0.047(3) 0.021(2) 0.031(2) 0.0019(18) 0.021(2) -0.003(2) C7 0.054(3) 0.026(2) 0.025(2) 0.0004(18) 0.023(2) 0.000(2) C8 0.047(3) 0.028(2) 0.029(2) 0.0022(19) 0.021(2) -0.004(2) C9 0.057(3) 0.025(2) 0.026(2) 0.0023(18) 0.020(2) -0.002(2) C10 0.055(3) 0.024(2) 0.033(3) -0.0013(19) 0.026(3) -0.006(2) C11 0.059(4) 0.043(3) 0.039(3) -0.006(2) 0.029(3) -0.009(3) C12 0.074(5) 0.051(3) 0.060(4) -0.016(3) 0.049(4) -0.027(3) C13 0.060(4) 0.029(3) 0.065(4) -0.011(2) 0.036(3) -0.008(3) C14 0.061(4) 0.036(3) 0.046(3) 0.004(2) 0.018(3) -0.012(3) C15 0.067(4) 0.038(3) 0.036(3) 0.006(2) 0.020(3) -0.010(3) C16 0.068(4) 0.019(2) 0.034(3) 0.0034(18) 0.034(3) -0.006(2) C17 0.072(4) 0.019(2) 0.030(3) 0.0020(18) 0.028(3) -0.005(2) C18 0.044(4) 0.025(2) 0.025(2) 0.0083(17) 0.016(2) 0.006(2) C19 0.042(3) 0.026(2) 0.029(3) 0.0045(18) 0.017(3) 0.007(2) C20 0.051(4) 0.032(2) 0.027(2) 0.0030(19) 0.021(3) 0.004(2) C21 0.051(4) 0.025(2) 0.035(3) 0.0052(19) 0.016(3) 0.001(2) C22 0.063(4) 0.029(2) 0.029(3) 0.000(2) 0.018(3) 0.009(3) C23 0.054(4) 0.027(2) 0.034(3) 0.0031(19) 0.023(3) 0.007(2) C24 0.080(5) 0.033(3) 0.037(3) 0.008(2) 0.034(3) 0.014(3) C25 0.096(6) 0.085(5) 0.058(4) 0.007(4) 0.059(4) 0.009(4) C26 0.207(11) 0.045(3) 0.063(5) 0.001(3) 0.089(6) 0.007(4) C27 0.088(5) 0.070(4) 0.033(3) 0.007(3) 0.026(3) 0.011(4) C28 0.058(4) 0.044(3) 0.031(3) 0.007(2) 0.026(3) 0.003(3) C29 0.116(7) 0.052(4) 0.048(4) 0.016(3) 0.033(4) 0.028(4) C30 0.067(6) 0.155(19) 0.062(7) 0.021(8) 0.044(6) -0.015(8) C31 0.096(11) 0.08(3) 0.10(2) 0.031(19) 0.083(15) 0.023(11) C32 0.136(8) 0.049(3) 0.043(3) 0.001(3) 0.050(4) -0.004(4) _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 C7 1.449(7) . ? O1 C9 1.464(6) . ? O2 C17 1.194(7) . ? O3 C16 1.238(7) . ? N1 C16 1.368(8) . ? N1 C17 1.433(8) . ? N1 C18 1.459(6) . ? C1 C6 1.380(7) . ? C1 C2 1.414(8) . ? C1 H1TE 0.9500 . ? C2 C3 1.359(9) . ? C2 H5ST 0.9500 . ? C3 C4 1.367(9) . ? C3 H7DQ 0.9500 . ? C4 C5 1.370(9) . ? C4 H7SN 0.9500 . ? C5 C6 1.379(8) . ? C5 H2SB 0.9500 . ? C6 C7 1.501(8) . ? C7 C16 1.516(6) . ? C7 C8 1.542(7) . ? C7 C9 2.025(9) . ? C8 C9 1.537(8) . ? C8 H3EA 0.9900 . ? C8 H3EB 0.9900 . ? C9 C10 1.493(9) . ? C9 C17 1.542(6) . ? C10 C15 1.371(8) . ? C10 C11 1.384(8) . ? C11 C12 1.404(9) . ? C11 H1ND 0.9500 . ? C12 C13 1.381(10) . ? C12 H0LO 0.9500 . ? C13 C14 1.367(9) . ? C13 H0DC 0.9500 . ? C14 C15 1.398(10) . ? C14 H8MD 0.9500 . ? C15 H8QQ 0.9500 . ? C18 C19 1.387(7) . ? C18 C23 1.391(7) . ? C19 C20 1.383(7) . ? C19 H8OL 0.9500 . ? C20 C21 1.392(7) . ? C20 C28 1.523(7) . ? C21 C22 1.368(8) . ? C21 H3WJ 0.9500 . ? C22 C23 1.406(7) . ? C22 H5HK 0.9500 . ? C23 C24 1.536(7) . ? C24 C27 1.522(10) . ? C24 C26 1.523(8) . ? C24 C25 1.542(11) . ? C25 H5BA 0.9800 . ? C25 H5BB 0.9800 . ? C25 H5BC 0.9800 . ? C26 H0WA 0.9800 . ? C26 H0WB 0.9800 . ? C26 H0WC 0.9800 . ? C27 H3GA 0.9800 . ? C27 H3GB 0.9800 . ? C27 H3GC 0.9800 . ? C28 C32 1.510(9) . ? C28 C29 1.512(9) . ? C28 C30 1.553(14) . ? C28 C31 1.58(4) . ? C29 H4KA 0.9800 . ? C29 H4KB 0.9800 . ? C29 H4KC 0.9800 . ? C30 H1A1 0.9800 . ? C30 H1A2 0.9800 . ? C30 H1A3 0.9800 . ? C31 H1B1 0.9800 . ? C31 H1B2 0.9800 . ? C31 H1B3 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 C7 O1 C9 88.1(4) . . ? C16 N1 C17 117.9(4) . . ? C16 N1 C18 120.8(5) . . ? C17 N1 C18 119.7(4) . . ? C6 C1 C2 120.1(5) . . ? C6 C1 H1TE 120.0 . . ? C2 C1 H1TE 120.0 . . ? C3 C2 C1 119.0(5) . . ? C3 C2 H5ST 120.5 . . ? C1 C2 H5ST 120.5 . . ? C2 C3 C4 120.6(6) . . ? C2 C3 H7DQ 119.7 . . ? C4 C3 H7DQ 119.7 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H7SN 119.5 . . ? C5 C4 H7SN 119.5 . . ? C4 C5 C6 120.2(5) . . ? C4 C5 H2SB 119.9 . . ? C6 C5 H2SB 119.9 . . ? C5 C6 C1 119.2(5) . . ? C5 C6 C7 120.7(4) . . ? C1 C6 C7 120.1(5) . . ? O1 C7 C6 114.1(4) . . ? O1 C7 C16 105.4(4) . . ? C6 C7 C16 114.5(5) . . ? O1 C7 C8 90.2(4) . . ? C6 C7 C8 122.4(4) . . ? C16 C7 C8 106.8(4) . . ? O1 C7 C9 46.3(3) . . ? C6 C7 C9 148.3(4) . . ? C16 C7 C9 96.3(4) . . ? C8 C7 C9 48.7(3) . . ? C9 C8 C7 82.3(4) . . ? C9 C8 H3EA 114.9 . . ? C7 C8 H3EA 114.9 . . ? C9 C8 H3EB 114.9 . . ? C7 C8 H3EB 114.9 . . ? H3EA C8 H3EB 112.0 . . ? O1 C9 C10 115.2(4) . . ? O1 C9 C8 89.9(4) . . ? C10 C9 C8 120.9(4) . . ? O1 C9 C17 105.8(4) . . ? C10 C9 C17 113.7(5) . . ? C8 C9 C17 108.3(4) . . ? O1 C9 C7 45.6(3) . . ? C10 C9 C7 147.9(4) . . ? C8 C9 C7 49.0(3) . . ? C17 C9 C7 97.7(4) . . ? C15 C10 C11 120.1(6) . . ? C15 C10 C9 121.3(5) . . ? C11 C10 C9 118.6(5) . . ? C10 C11 C12 119.4(6) . . ? C10 C11 H1ND 120.3 . . ? C12 C11 H1ND 120.3 . . ? C13 C12 C11 120.0(6) . . ? C13 C12 H0LO 120.0 . . ? C11 C12 H0LO 120.0 . . ? C14 C13 C12 120.1(7) . . ? C14 C13 H0DC 119.9 . . ? C12 C13 H0DC 119.9 . . ? C13 C14 C15 120.1(6) . . ? C13 C14 H8MD 120.0 . . ? C15 C14 H8MD 120.0 . . ? C10 C15 C14 120.3(6) . . ? C10 C15 H8QQ 119.9 . . ? C14 C15 H8QQ 119.9 . . ? O3 C16 N1 120.7(4) . . ? O3 C16 C7 123.9(5) . . ? N1 C16 C7 115.4(5) . . ? O2 C17 N1 121.4(4) . . ? O2 C17 C9 127.1(6) . . ? N1 C17 C9 111.5(5) . . ? C19 C18 C23 123.6(4) . . ? C19 C18 N1 114.4(4) . . ? C23 C18 N1 121.9(4) . . ? C20 C19 C18 121.6(4) . . ? C20 C19 H8OL 119.2 . . ? C18 C19 H8OL 119.2 . . ? C19 C20 C21 115.8(4) . . ? C19 C20 C28 122.9(5) . . ? C21 C20 C28 121.3(5) . . ? C22 C21 C20 122.1(5) . . ? C22 C21 H3WJ 119.0 . . ? C20 C21 H3WJ 119.0 . . ? C21 C22 C23 123.5(5) . . ? C21 C22 H5HK 118.3 . . ? C23 C22 H5HK 118.3 . . ? C18 C23 C22 113.4(5) . . ? C18 C23 C24 125.4(5) . . ? C22 C23 C24 121.2(5) . . ? C27 C24 C26 108.7(7) . . ? C27 C24 C23 111.0(5) . . ? C26 C24 C23 111.7(5) . . ? C27 C24 C25 107.3(6) . . ? C26 C24 C25 106.3(7) . . ? C23 C24 C25 111.6(5) . . ? C24 C25 H5BA 109.5 . . ? C24 C25 H5BB 109.5 . . ? H5BA C25 H5BB 109.5 . . ? C24 C25 H5BC 109.5 . . ? H5BA C25 H5BC 109.5 . . ? H5BB C25 H5BC 109.5 . . ? C24 C26 H0WA 109.5 . . ? C24 C26 H0WB 109.5 . . ? H0WA C26 H0WB 109.5 . . ? C24 C26 H0WC 109.5 . . ? H0WA C26 H0WC 109.5 . . ? H0WB C26 H0WC 109.5 . . ? C24 C27 H3GA 109.5 . . ? C24 C27 H3GB 109.5 . . ? H3GA C27 H3GB 109.5 . . ? C24 C27 H3GC 109.5 . . ? H3GA C27 H3GC 109.5 . . ? H3GB C27 H3GC 109.5 . . ? C32 C28 C29 106.5(6) . . ? C32 C28 C20 111.9(5) . . ? C29 C28 C20 110.9(5) . . ? C32 C28 C30 113.8(12) . . ? C29 C28 C30 105.6(13) . . ? C20 C28 C30 107.9(7) . . ? C32 C28 C31 86(3) . . ? C29 C28 C31 131(2) . . ? C20 C28 C31 106.7(17) . . ? C30 C28 C31 31.6(18) . . ? C28 C29 H4KA 109.5 . . ? C28 C29 H4KB 109.5 . . ? H4KA C29 H4KB 109.5 . . ? C28 C29 H4KC 109.5 . . ? H4KA C29 H4KC 109.5 . . ? H4KB C29 H4KC 109.5 . . ? C28 C30 H1A1 109.5 . . ? C28 C30 H1A2 109.5 . . ? H1A1 C30 H1A2 109.5 . . ? C28 C30 H1A3 109.5 . . ? H1A1 C30 H1A3 109.5 . . ? H1A2 C30 H1A3 109.5 . . ? C28 C31 H1B1 109.5 . . ? C28 C31 H1B2 109.5 . . ? H1B1 C31 H1B2 109.5 . . ? C28 C31 H1B3 109.5 . . ? H1B1 C31 H1B3 109.5 . . ? H1B2 C31 H1B3 109.5 . . ? C28 C32 H32A 109.5 . . ? C28 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C28 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 66.65 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.521 _refine_diff_density_min -0.919 _refine_diff_density_rms 0.114 _database_code_depnum_ccdc_archive 'CCDC 942927'