# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H31 N3 O3' _chemical_formula_sum 'C23 H31 N3 O3' _chemical_formula_weight 397.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6351(12) _cell_length_b 8.8110(8) _cell_length_c 16.5849(19) _cell_angle_alpha 77.500(9) _cell_angle_beta 86.211(10) _cell_angle_gamma 76.035(10) _cell_volume 1057.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 22704 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour 'dark violet' _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.083 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 1 0 0.167 -1 -1 0 0.172 0 1 0 0.137 0 -1 0 0.190 0 0 1 0.034 0 0 -1 0.031 1 0 0 0.276 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22654 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4809 _reflns_number_gt 3926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0472P)^2^+0.5190P] 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 4809 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 N2 N 0.41244(17) 0.81427(14) 0.28131(8) 0.0254(3) Uani 1 1 d . . . O2 O 0.38484(16) 0.39584(13) 0.22556(7) 0.0338(3) Uani 1 1 d . . . O1 O 0.23467(16) 0.75263(14) 0.39290(7) 0.0358(3) Uani 1 1 d . . . O3 O 0.59946(16) 0.86976(14) 0.17294(7) 0.0344(3) Uani 1 1 d . . . C8 C 0.7920(2) 0.29901(17) -0.01789(9) 0.0249(3) Uani 1 1 d . . . C2 C 0.3997(2) 0.52242(18) 0.24012(9) 0.0251(3) Uani 1 1 d . . . N3 N 0.91542(19) -0.06550(15) -0.15374(8) 0.0309(3) Uani 1 1 d . . . C20 C 0.6287(2) 1.04910(17) 0.39941(9) 0.0272(3) Uani 1 1 d . . . H20A H 0.5233 1.0998 0.4280 0.033 Uiso 1 1 d R . . H20B H 0.6540 1.1275 0.3521 0.033 Uiso 1 1 d R . . C4 C 0.5123(2) 0.77744(18) 0.21189(9) 0.0253(3) Uani 1 1 d . . . C21 C 0.7888(2) 0.99533(19) 0.45689(10) 0.0322(4) Uani 1 1 d . . . H21A H 0.7703 0.9089 0.5004 0.039 Uiso 1 1 d R . . H21B H 0.8003 1.0831 0.4802 0.039 Uiso 1 1 d R . . H21C H 0.8969 0.9601 0.4264 0.039 Uiso 1 1 d R . . C10 C 0.7626(2) 0.04178(18) -0.03815(9) 0.0277(3) Uani 1 1 d . . . H10 H 0.7138 -0.0473 -0.0212 0.033 Uiso 1 1 d R . . C12 C 0.9491(2) 0.18868(18) -0.13220(9) 0.0259(3) Uani 1 1 d . . . H12 H 1.0264 0.1981 -0.1778 0.031 Uiso 1 1 d R . . C5 C 0.6115(2) 0.58512(18) 0.12443(9) 0.0266(3) Uani 1 1 d . . . H5 H 0.6737 0.6605 0.0972 0.032 Uiso 1 1 d R . . N1 N 0.31238(17) 0.57367(14) 0.30936(7) 0.0246(3) Uani 1 1 d . . . C7 C 0.7499(2) 0.42883(18) 0.02487(9) 0.0270(3) Uani 1 1 d . . . H7 H 0.8057 0.5125 0.0044 0.032 Uiso 1 1 d R . . C14 C 0.2161(2) 0.46669(18) 0.36576(9) 0.0274(3) Uani 1 1 d . . . H14A H 0.2359 0.4718 0.4222 0.033 Uiso 1 1 d R . . H14B H 0.2664 0.3577 0.3595 0.033 Uiso 1 1 d R . . C3 C 0.5074(2) 0.62563(17) 0.19038(9) 0.0244(3) Uani 1 1 d . . . C13 C 0.9061(2) 0.30728(18) -0.08768(9) 0.0260(3) Uani 1 1 d . . . H13 H 0.9544 0.3966 -0.1044 0.031 Uiso 1 1 d R . . C6 C 0.6387(2) 0.44545(18) 0.09157(9) 0.0273(3) Uani 1 1 d . . . H6 H 0.5806 0.3649 0.1156 0.033 Uiso 1 1 d R . . C11 C 0.8767(2) 0.05193(17) -0.10915(9) 0.0252(3) Uani 1 1 d . . . C1 C 0.3143(2) 0.71593(18) 0.33166(9) 0.0254(3) Uani 1 1 d . . . C18 C 0.4321(2) 0.95507(17) 0.31111(9) 0.0270(3) Uani 1 1 d . . . H18A H 0.3218 0.9985 0.3391 0.032 Uiso 1 1 d R . . H18B H 0.4531 1.0370 0.2646 0.032 Uiso 1 1 d R . . C19 C 0.5891(2) 0.90900(17) 0.36993(9) 0.0271(3) Uani 1 1 d . . . H19A H 0.6963 0.8574 0.3427 0.033 Uiso 1 1 d R . . H19B H 0.5632 0.8316 0.4176 0.033 Uiso 1 1 d R . . C9 C 0.7228(2) 0.16080(18) 0.00580(9) 0.0267(3) Uani 1 1 d . . . H9 H 0.6482 0.1507 0.0524 0.032 Uiso 1 1 d R . . C17 C -0.2800(2) 0.4363(2) 0.40063(12) 0.0386(4) Uani 1 1 d . . . H17A H -0.3272 0.5421 0.4104 0.046 Uiso 1 1 d R . . H17B H -0.3319 0.3617 0.4400 0.046 Uiso 1 1 d R . . H17C H -0.3098 0.4330 0.3458 0.046 Uiso 1 1 d R . . C15 C 0.0160(2) 0.50791(19) 0.35102(10) 0.0316(3) Uani 1 1 d . . . H15A H -0.0048 0.5045 0.2944 0.038 Uiso 1 1 d R . . H15B H -0.0358 0.6158 0.3587 0.038 Uiso 1 1 d R . . C16 C -0.0774(2) 0.39224(19) 0.40936(10) 0.0309(3) Uani 1 1 d . . . H16A H -0.0485 0.3901 0.4658 0.037 Uiso 1 1 d R . . H16B H -0.0306 0.2856 0.3989 0.037 Uiso 1 1 d R . . C23 C 1.0496(3) -0.0637(2) -0.22008(11) 0.0377(4) Uani 1 1 d . . . H23A H 1.0051 0.0234 -0.2651 0.045 Uiso 1 1 d R . . H23B H 1.0729 -0.1626 -0.2387 0.045 Uiso 1 1 d R . . H23C H 1.1592 -0.0505 -0.2003 0.045 Uiso 1 1 d R . . C22 C 0.8340(3) -0.20153(19) -0.13217(11) 0.0371(4) Uani 1 1 d . . . H22A H 0.8857 -0.2699 -0.0821 0.045 Uiso 1 1 d R . . H22B H 0.8560 -0.2599 -0.1759 0.045 Uiso 1 1 d R . . H22C H 0.7063 -0.1649 -0.1243 0.045 Uiso 1 1 d 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 N2 0.0270(7) 0.0250(6) 0.0269(6) -0.0069(5) -0.0022(5) -0.0093(5) O2 0.0431(7) 0.0305(6) 0.0352(6) -0.0133(5) 0.0077(5) -0.0189(5) O1 0.0402(7) 0.0376(6) 0.0348(6) -0.0160(5) 0.0116(5) -0.0145(5) O3 0.0386(7) 0.0354(6) 0.0363(6) -0.0106(5) 0.0068(5) -0.0212(5) C8 0.0247(7) 0.0277(7) 0.0226(7) -0.0037(6) -0.0020(6) -0.0079(6) C2 0.0252(7) 0.0274(7) 0.0247(7) -0.0062(6) -0.0019(6) -0.0085(6) N3 0.0373(8) 0.0263(6) 0.0314(7) -0.0071(5) 0.0010(6) -0.0113(6) C20 0.0304(8) 0.0236(7) 0.0302(8) -0.0079(6) -0.0020(6) -0.0089(6) C4 0.0249(7) 0.0282(7) 0.0247(7) -0.0048(6) -0.0025(6) -0.0099(6) C21 0.0324(9) 0.0321(8) 0.0356(8) -0.0099(7) -0.0046(7) -0.0106(7) C10 0.0292(8) 0.0263(7) 0.0280(7) -0.0002(6) -0.0017(6) -0.0118(6) C12 0.0261(7) 0.0285(7) 0.0237(7) -0.0044(6) 0.0028(6) -0.0093(6) C5 0.0259(8) 0.0311(8) 0.0238(7) -0.0034(6) -0.0025(6) -0.0104(6) N1 0.0248(6) 0.0259(6) 0.0248(6) -0.0052(5) 0.0024(5) -0.0098(5) C7 0.0270(8) 0.0291(7) 0.0261(7) -0.0035(6) -0.0027(6) -0.0100(6) C14 0.0297(8) 0.0266(7) 0.0261(7) -0.0030(6) 0.0020(6) -0.0098(6) C3 0.0242(7) 0.0271(7) 0.0243(7) -0.0056(6) -0.0032(6) -0.0094(6) C13 0.0262(8) 0.0259(7) 0.0269(7) -0.0027(6) -0.0011(6) -0.0102(6) C6 0.0280(8) 0.0302(8) 0.0254(7) -0.0065(6) -0.0010(6) -0.0094(6) C11 0.0263(7) 0.0242(7) 0.0246(7) -0.0035(6) -0.0034(6) -0.0055(6) C1 0.0240(7) 0.0272(7) 0.0263(7) -0.0071(6) -0.0009(6) -0.0066(6) C18 0.0295(8) 0.0233(7) 0.0311(8) -0.0087(6) -0.0030(6) -0.0079(6) C19 0.0303(8) 0.0221(7) 0.0308(8) -0.0076(6) -0.0032(6) -0.0069(6) C9 0.0259(8) 0.0314(8) 0.0227(7) -0.0019(6) 0.0004(6) -0.0096(6) C17 0.0310(9) 0.0310(8) 0.0517(10) 0.0002(7) -0.0022(8) -0.0106(7) C15 0.0287(8) 0.0288(8) 0.0363(8) -0.0002(6) -0.0023(7) -0.0102(6) C16 0.0283(8) 0.0290(8) 0.0343(8) -0.0010(6) -0.0007(6) -0.0093(6) C23 0.0444(10) 0.0344(9) 0.0363(9) -0.0150(7) 0.0057(8) -0.0080(7) C22 0.0426(10) 0.0283(8) 0.0441(10) -0.0085(7) -0.0066(8) -0.0128(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 N2 C1 1.3879(19) . ? N2 C4 1.3922(19) . ? N2 C18 1.4734(18) . ? O2 C2 1.2232(18) . ? O1 C1 1.2132(18) . ? O3 C4 1.2243(18) . ? C8 C13 1.402(2) . ? C8 C9 1.412(2) . ? C8 C7 1.435(2) . ? C2 N1 1.3946(19) . ? C2 C3 1.460(2) . ? N3 C11 1.364(2) . ? N3 C22 1.448(2) . ? N3 C23 1.453(2) . ? C20 C21 1.519(2) . ? C20 C19 1.5216(19) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C4 C3 1.466(2) . ? C21 H21A 0.9600 . ? C21 H21B 0.9599 . ? C21 H21C 0.9600 . ? C10 C9 1.368(2) . ? C10 C11 1.418(2) . ? C10 H10 0.9300 . ? C12 C13 1.372(2) . ? C12 C11 1.413(2) . ? C12 H12 0.9300 . ? C5 C3 1.368(2) . ? C5 C6 1.417(2) . ? C5 H5 0.9300 . ? N1 C1 1.3852(19) . ? N1 C14 1.4716(18) . ? C7 C6 1.361(2) . ? C7 H7 0.9300 . ? C14 C15 1.506(2) . ? C14 H14A 0.9701 . ? C14 H14B 0.9700 . ? C13 H13 0.9300 . ? C6 H6 0.9299 . ? C18 C19 1.517(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C9 H9 0.9300 . ? C17 C16 1.510(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9601 . ? C15 C16 1.522(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9702 . ? C16 H16B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9599 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C4 124.54(12) . . ? C1 N2 C18 116.57(12) . . ? C4 N2 C18 118.25(12) . . ? C13 C8 C9 116.89(13) . . ? C13 C8 C7 119.59(13) . . ? C9 C8 C7 123.52(14) . . ? O2 C2 N1 119.39(13) . . ? O2 C2 C3 124.44(14) . . ? N1 C2 C3 116.16(13) . . ? C11 N3 C22 120.79(14) . . ? C11 N3 C23 120.91(13) . . ? C22 N3 C23 118.14(13) . . ? C21 C20 C19 111.41(12) . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? O3 C4 N2 119.69(13) . . ? O3 C4 C3 123.63(14) . . ? N2 C4 C3 116.67(12) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C9 C10 C11 121.14(14) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C13 C12 C11 120.41(14) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.7 . . ? C3 C5 C6 129.62(14) . . ? C3 C5 H5 115.1 . . ? C6 C5 H5 115.3 . . ? C1 N1 C2 125.19(12) . . ? C1 N1 C14 116.55(12) . . ? C2 N1 C14 118.21(12) . . ? C6 C7 C8 128.40(14) . . ? C6 C7 H7 115.7 . . ? C8 C7 H7 115.9 . . ? N1 C14 C15 113.28(12) . . ? N1 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? N1 C14 H14B 108.9 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.7 . . ? C5 C3 C2 122.75(13) . . ? C5 C3 C4 117.06(13) . . ? C2 C3 C4 120.15(13) . . ? C12 C13 C8 122.49(13) . . ? C12 C13 H13 118.8 . . ? C8 C13 H13 118.7 . . ? C7 C6 C5 120.07(14) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 120.0 . . ? N3 C11 C12 121.05(14) . . ? N3 C11 C10 121.45(13) . . ? C12 C11 C10 117.49(13) . . ? O1 C1 N1 121.44(14) . . ? O1 C1 N2 121.37(14) . . ? N1 C1 N2 117.19(13) . . ? N2 C18 C19 110.15(12) . . ? N2 C18 H18A 109.7 . . ? C19 C18 H18A 109.7 . . ? N2 C18 H18B 109.6 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C18 C19 C20 114.08(12) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.6 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.6 . . ? C10 C9 C8 121.57(14) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.1 . . ? C16 C17 H17A 109.6 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C15 C16 111.48(13) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C15 113.11(13) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? N3 C23 H23A 109.4 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.4 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.300 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 932394' ####################################################################### # # 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_shelxl2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H29 N3 O3' _chemical_formula_sum 'C21 H29 N3 O3' _chemical_formula_weight 371.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8780(4) _cell_length_b 8.8850(8) _cell_length_c 14.7671(16) _cell_angle_alpha 82.567(7) _cell_angle_beta 84.778(7) _cell_angle_gamma 76.935(6) _cell_volume 996.38(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18454 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.083 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.113 0 1 0 0.060 0 0 1 0.171 0 -1 0 0.175 -1 0 0 0.124 1 0 0 0.243 -1 0 1 0.068 1 0 -1 0.146 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.697 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18398 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4531 _reflns_number_gt 2710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0529P)^2^+0.6360P] 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 4531 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1326 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.1792 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 O3 O 0.1597(3) 0.7848(2) 0.14385(14) 0.0587(6) Uani 1 1 d . . . O2 O -0.0873(3) 0.3394(2) 0.20054(15) 0.0650(6) Uani 1 1 d . . . C6 C 0.2089(3) 0.3726(3) 0.03638(17) 0.0398(6) Uani 1 1 d . . . N3 N 0.3883(3) 0.0046(3) -0.12574(17) 0.0513(6) Uani 1 1 d . . . C11 C 0.3290(4) 0.3814(3) -0.04005(18) 0.0434(6) Uani 1 1 d . . . H11 H 0.3687 0.4730 -0.0552 0.052 Uiso 1 1 d R . . C8 C 0.2135(4) 0.1102(3) 0.00307(19) 0.0483(7) Uani 1 1 d . . . H8 H 0.1745 0.0184 0.0186 0.058 Uiso 1 1 d R . . C4 C 0.0622(4) 0.7047(3) 0.18451(18) 0.0427(6) Uani 1 1 d . . . C12 C -0.2596(4) 0.4392(3) 0.35251(19) 0.0483(7) Uani 1 1 d . . . H12A H -0.2523 0.4586 0.4150 0.058 Uiso 1 1 d R . . H12B H -0.2111 0.3296 0.3483 0.058 Uiso 1 1 d R . . N2 N -0.0440(3) 0.7594(2) 0.25859(15) 0.0420(5) Uani 1 1 d . . . N1 N -0.1531(3) 0.5309(3) 0.29107(15) 0.0422(5) Uani 1 1 d . . . C7 C 0.1553(4) 0.2300(3) 0.05494(19) 0.0461(7) Uani 1 1 d . . . H7 H 0.0768 0.2173 0.1048 0.055 Uiso 1 1 d R . . O1 O -0.2356(3) 0.7277(3) 0.37956(16) 0.0664(6) Uani 1 1 d . . . C5 C 0.1604(3) 0.5050(3) 0.08520(17) 0.0408(6) Uani 1 1 d . . . H5 H 0.2172 0.5827 0.0591 0.049 Uiso 1 1 d R . . C9 C 0.3322(3) 0.1226(3) -0.07390(18) 0.0411(6) Uani 1 1 d . . . C3 C 0.0536(3) 0.5515(3) 0.16005(17) 0.0391(6) Uani 1 1 d . . . C2 C -0.0634(4) 0.4648(3) 0.21491(18) 0.0435(6) Uani 1 1 d . . . C18 C 0.1453(4) 1.0227(3) 0.38981(19) 0.0466(7) Uani 1 1 d . . . H18A H 0.0385 1.0779 0.4194 0.056 Uiso 1 1 d R . . H18B H 0.1768 1.0900 0.3369 0.056 Uiso 1 1 d R . . C1 C -0.1501(4) 0.6762(3) 0.31355(19) 0.0458(7) Uani 1 1 d . . . C13 C -0.4475(4) 0.4748(4) 0.3313(2) 0.0565(8) Uani 1 1 d . . . H13A H -0.4557 0.4573 0.2685 0.068 Uiso 1 1 d R . . H13B H -0.4979 0.5835 0.3372 0.068 Uiso 1 1 d R . . C14 C -0.5514(4) 0.3742(4) 0.3951(2) 0.0582(8) Uani 1 1 d . . . H14A H -0.5054 0.2661 0.3858 0.070 Uiso 1 1 d R . . H14B H -0.5348 0.3857 0.4579 0.070 Uiso 1 1 d R . . C17 C 0.1126(4) 0.8763(3) 0.35828(19) 0.0454(7) Uani 1 1 d . . . H17A H 0.2214 0.8188 0.3317 0.054 Uiso 1 1 d R . . H17B H 0.0767 0.8114 0.4112 0.054 Uiso 1 1 d R . . C16 C -0.0250(4) 0.9062(3) 0.2892(2) 0.0474(7) Uani 1 1 d . . . H16A H -0.1358 0.9588 0.3162 0.057 Uiso 1 1 d R . . H16B H 0.0080 0.9738 0.2368 0.057 Uiso 1 1 d R . . C10 C 0.3895(4) 0.2639(3) -0.09276(19) 0.0471(7) Uani 1 1 d . . . H10 H 0.4697 0.2764 -0.1419 0.056 Uiso 1 1 d R . . C20 C 0.3253(4) -0.1382(3) -0.1077(2) 0.0600(8) Uani 1 1 d . . . H20A H 0.3660 -0.1932 -0.0507 0.072 Uiso 1 1 d R . . H20B H 0.3684 -0.2019 -0.1562 0.072 Uiso 1 1 d R . . H20C H 0.2000 -0.1142 -0.1042 0.072 Uiso 1 1 d R . . C19 C 0.2889(4) 0.9876(4) 0.4552(2) 0.0587(8) Uani 1 1 d . . . H19A H 0.2619 0.9157 0.5058 0.070 Uiso 1 1 d R . . H19B H 0.2985 1.0821 0.4773 0.070 Uiso 1 1 d R . . H19C H 0.3975 0.9428 0.4243 0.070 Uiso 1 1 d R . . C15 C -0.7412(4) 0.4136(4) 0.3811(3) 0.0738(10) Uani 1 1 d . . . H15A H -0.7875 0.5210 0.3894 0.089 Uiso 1 1 d R . . H15B H -0.7998 0.3493 0.4246 0.089 Uiso 1 1 d R . . H15C H -0.7592 0.3964 0.3202 0.089 Uiso 1 1 d R . . C21 C 0.5148(4) 0.0151(4) -0.2027(2) 0.0624(9) Uani 1 1 d . . . H21A H 0.4589 0.0823 -0.2527 0.075 Uiso 1 1 d R . . H21B H 0.5613 -0.0866 -0.2213 0.075 Uiso 1 1 d R . . H21C H 0.6078 0.0564 -0.1850 0.075 Uiso 1 1 d 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 O3 0.0713(15) 0.0556(12) 0.0588(13) -0.0090(10) 0.0086(11) -0.0373(11) O2 0.0772(16) 0.0575(13) 0.0711(14) -0.0254(11) 0.0280(12) -0.0396(12) C6 0.0375(15) 0.0460(15) 0.0377(14) -0.0007(11) -0.0054(11) -0.0141(12) N3 0.0499(15) 0.0494(14) 0.0560(14) -0.0126(12) 0.0041(12) -0.0130(11) C11 0.0454(16) 0.0476(15) 0.0414(14) -0.0028(12) 0.0015(12) -0.0214(13) C8 0.0504(17) 0.0428(15) 0.0519(16) -0.0004(13) 0.0038(13) -0.0162(13) C4 0.0439(16) 0.0461(15) 0.0414(14) -0.0017(12) -0.0086(12) -0.0162(13) C12 0.0517(17) 0.0490(16) 0.0451(15) -0.0021(13) 0.0068(13) -0.0184(14) N2 0.0458(13) 0.0396(12) 0.0449(12) -0.0076(10) -0.0040(10) -0.0160(10) N1 0.0427(13) 0.0453(13) 0.0410(12) -0.0061(10) 0.0033(10) -0.0159(10) C7 0.0467(16) 0.0457(15) 0.0459(15) -0.0007(12) 0.0064(13) -0.0163(13) O1 0.0701(15) 0.0638(14) 0.0705(14) -0.0273(12) 0.0210(12) -0.0245(12) C5 0.0433(15) 0.0456(15) 0.0373(14) 0.0022(12) -0.0067(12) -0.0198(12) C9 0.0344(14) 0.0467(15) 0.0423(14) -0.0038(12) -0.0058(12) -0.0080(12) C3 0.0386(15) 0.0432(14) 0.0379(14) -0.0024(11) -0.0034(11) -0.0147(12) C2 0.0420(16) 0.0470(16) 0.0446(15) -0.0068(12) -0.0008(12) -0.0159(12) C18 0.0494(17) 0.0426(15) 0.0510(16) -0.0091(13) -0.0025(13) -0.0147(13) C1 0.0420(16) 0.0490(16) 0.0487(16) -0.0108(13) -0.0020(13) -0.0123(13) C13 0.0492(18) 0.0511(17) 0.069(2) 0.0055(15) -0.0048(15) -0.0166(14) C14 0.0517(19) 0.0564(18) 0.067(2) 0.0051(15) -0.0042(15) -0.0193(15) C17 0.0452(16) 0.0390(14) 0.0533(16) -0.0091(12) -0.0034(13) -0.0096(12) C16 0.0531(17) 0.0390(14) 0.0526(17) -0.0088(12) -0.0066(14) -0.0118(13) C10 0.0436(16) 0.0560(17) 0.0433(15) -0.0045(13) 0.0058(12) -0.0185(14) C20 0.068(2) 0.0491(17) 0.066(2) -0.0124(15) -0.0003(17) -0.0166(16) C19 0.061(2) 0.0618(19) 0.0597(19) -0.0121(15) -0.0110(16) -0.0208(16) C15 0.056(2) 0.060(2) 0.102(3) 0.0117(19) -0.006(2) -0.0160(17) C21 0.064(2) 0.066(2) 0.0578(19) -0.0195(16) 0.0121(16) -0.0158(17) _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 O3 C4 1.229(3) . ? O2 C2 1.218(3) . ? C6 C7 1.411(4) . ? C6 C11 1.411(4) . ? C6 C5 1.420(4) . ? N3 C9 1.348(3) . ? N3 C21 1.449(4) . ? N3 C20 1.449(4) . ? C11 C10 1.357(4) . ? C11 H11 0.9300 . ? C8 C7 1.362(4) . ? C8 C9 1.414(4) . ? C8 H8 0.9301 . ? C4 N2 1.386(3) . ? C4 C3 1.470(4) . ? C12 N1 1.473(3) . ? C12 C13 1.496(4) . ? C12 H12A 0.9699 . ? C12 H12B 0.9700 . ? N2 C1 1.380(3) . ? N2 C16 1.477(3) . ? N1 C1 1.379(3) . ? N1 C2 1.396(3) . ? C7 H7 0.9299 . ? O1 C1 1.213(3) . ? C5 C3 1.375(4) . ? C5 H5 0.9300 . ? C9 C10 1.414(4) . ? C3 C2 1.457(4) . ? C18 C19 1.507(4) . ? C18 C17 1.518(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C13 C14 1.527(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9701 . ? C14 C15 1.484(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9699 . ? C17 C16 1.512(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C10 H10 0.9301 . ? C20 H20A 0.9599 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9601 . ? C15 H15C 0.9600 . ? C21 H21A 0.9599 . ? C21 H21B 0.9600 . ? C21 H21C 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 C7 C6 C11 114.7(2) . . ? C7 C6 C5 128.6(2) . . ? C11 C6 C5 116.7(2) . . ? C9 N3 C21 121.3(2) . . ? C9 N3 C20 121.9(2) . . ? C21 N3 C20 116.8(2) . . ? C10 C11 C6 123.7(2) . . ? C10 C11 H11 118.2 . . ? C6 C11 H11 118.1 . . ? C7 C8 C9 121.4(3) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.3 . . ? O3 C4 N2 118.7(2) . . ? O3 C4 C3 123.6(3) . . ? N2 C4 C3 117.6(2) . . ? N1 C12 C13 113.7(2) . . ? N1 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N1 C12 H12B 108.8 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.7 . . ? C1 N2 C4 124.3(2) . . ? C1 N2 C16 117.0(2) . . ? C4 N2 C16 118.2(2) . . ? C1 N1 C2 125.1(2) . . ? C1 N1 C12 117.1(2) . . ? C2 N1 C12 117.8(2) . . ? C8 C7 C6 122.9(3) . . ? C8 C7 H7 118.6 . . ? C6 C7 H7 118.5 . . ? C3 C5 C6 138.3(2) . . ? C3 C5 H5 110.8 . . ? C6 C5 H5 110.9 . . ? N3 C9 C8 121.3(2) . . ? N3 C9 C10 122.2(2) . . ? C8 C9 C10 116.5(2) . . ? C5 C3 C2 126.5(2) . . ? C5 C3 C4 114.7(2) . . ? C2 C3 C4 118.8(2) . . ? O2 C2 N1 117.7(2) . . ? O2 C2 C3 125.6(3) . . ? N1 C2 C3 116.7(2) . . ? C19 C18 C17 112.2(2) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? O1 C1 N1 121.3(3) . . ? O1 C1 N2 121.4(3) . . ? N1 C1 N2 117.3(2) . . ? C12 C13 C14 111.7(2) . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 113.6(3) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.8 . . ? C16 C17 C18 114.1(2) . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.7 . . ? N2 C16 C17 111.1(2) . . ? N2 C16 H16A 109.6 . . ? C17 C16 H16A 109.5 . . ? N2 C16 H16B 109.3 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 108.0 . . ? C11 C10 C9 120.8(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? N3 C20 H20A 109.4 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C19 H19A 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.6 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 C15 H15A 109.4 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.4 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.302 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 932395'