Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Alessia Bacchi' _publ_contact_author_address ; Chimica Fisica Universita di Parma Parco Area delle Scienze 17A Parma ITALY ; _publ_contact_author_email ALESSIA.BACCHI@UNIPR.IT _publ_section_title ; Triarylcarbinol derivatives barter intermolecular interactions to accomodate substituents and create polymorphs ; loop_ _publ_author_name 'Alessia Bacchi' 'Elsa Bosetti' 'Mauro Carcelli' 'Paolo Pelagatti' 'Giancarlo Pelizzi' 'Dominga Rogolino' #==END ######################## data_alpha-MG-cryo _database_code_depnum_ccdc_archive 'CCDC 141881' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 N2 O' _chemical_formula_weight 346.46 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 'z, x, y' 'y, z, x' '-z+1/2, -x, y+1/2' '-y, z+1/2, -x+1/2' 'z+1/2, -x+1/2, -y' '-y+1/2, -z, x+1/2' '-z, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' '-z, -x, -y' '-y, -z, -x' 'z-1/2, x, -y-1/2' 'y, -z-1/2, x-1/2' '-z-1/2, x-1/2, y' 'y-1/2, z, -x-1/2' 'z, -x-1/2, y-1/2' '-y-1/2, z-1/2, x' _cell_length_a 25.078(2) _cell_length_b 25.078(2) _cell_length_c 25.078(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 15772(2) _cell_formula_units_Z 32 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5952 _exptl_absorpt_coefficient_mu 0.555 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54138 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11699 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 60.05 _reflns_number_total 3924 _reflns_number_gt 880 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3924 _refine_ls_number_parameters 283 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2378 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2691 _refine_ls_wR_factor_gt 0.2029 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 0.8050(2) 0.3267(2) 0.1025(2) 0.1505(17) Uani 1 1 d D . . H1 H 0.8303 0.3087 0.1150 0.21(5) Uiso 1 1 calc RD . . O2 O 0.8948(2) 0.3948(2) 0.1052(2) 0.338(8) Uani 1 3 d SD . . H2 H 0.9109 0.3878 0.1337 0.200 Uiso 0.33 1 calc PRD . . N1 N 0.6529(3) 0.1528(4) 0.2068(4) 0.212(3) Uani 1 1 d . . . N2 N 0.8957(3) 0.1660(3) -0.0719(3) 0.180(3) Uani 1 1 d . . . N3 N 1.0353(7) 0.2909(6) -0.0618(5) 0.193(5) Uani 0.67 1 d P . . C1 C 0.7715(3) 0.2929(3) 0.0698(3) 0.128(2) Uani 1 1 d D . . C2 C 0.74150(19) 0.2544(3) 0.1089(3) 0.127(2) Uani 1 1 d G . . C3 C 0.7210(3) 0.2728(2) 0.1570(4) 0.143(2) Uani 1 1 d G . . H3 H 0.7276 0.3085 0.1679 0.171 Uiso 1 1 calc R . . C4 C 0.6909(2) 0.2391(4) 0.18902(19) 0.150(3) Uani 1 1 d G . . H4 H 0.6769 0.2517 0.2219 0.180 Uiso 1 1 calc R . . C5 C 0.6814(2) 0.1869(4) 0.1730(3) 0.167(3) Uani 1 1 d G . . C6 C 0.7018(3) 0.16845(19) 0.1249(4) 0.183(3) Uani 1 1 d G . . H6 H 0.6953 0.1328 0.1139 0.220 Uiso 1 1 calc R . . C7 C 0.7319(2) 0.2022(4) 0.09284(19) 0.164(3) Uani 1 1 d G . . H7 H 0.7459 0.1896 0.0600 0.197 Uiso 1 1 calc R . . C8 C 0.7316(3) 0.3298(3) 0.04060(17) 0.126(2) Uani 1 1 d G . . C9 C 0.7493(2) 0.3799(4) 0.0247(3) 0.145(3) Uani 1 1 d G . . H9 H 0.7843 0.3913 0.0335 0.174 Uiso 1 1 calc R . . C10 C 0.7157(4) 0.41331(17) -0.0041(2) 0.159(3) Uani 1 1 d G . . H10 H 0.7278 0.4475 -0.0149 0.191 Uiso 1 1 calc R . . C11 C 0.6644(4) 0.3966(3) -0.01695(17) 0.188(4) Uani 1 1 d G . . H11 H 0.6415 0.4195 -0.0366 0.225 Uiso 1 1 calc R . . C12 C 0.64676(19) 0.3466(4) -0.0011(3) 0.176(3) Uani 1 1 d G . . H12 H 0.6117 0.3352 -0.0099 0.211 Uiso 1 1 calc R . . C13 C 0.6803(4) 0.31316(19) 0.0277(2) 0.153(3) Uani 1 1 d G . . H13 H 0.6683 0.2789 0.0386 0.184 Uiso 1 1 calc R . . C14 C 0.8053(3) 0.26182(19) 0.0293(3) 0.127(2) Uani 1 1 d G . . C15 C 0.8526(3) 0.2395(3) 0.0475(2) 0.144(2) Uani 1 1 d G . . H15 H 0.8642 0.2459 0.0830 0.173 Uiso 1 1 calc R . . C16 C 0.88304(19) 0.2077(2) 0.0137(4) 0.152(3) Uani 1 1 d G . . H16 H 0.9154 0.1925 0.0262 0.183 Uiso 1 1 calc R . . C17 C 0.8661(3) 0.1983(2) -0.0382(3) 0.140(2) Uani 1 1 d G . . C18 C 0.8187(3) 0.2207(3) -0.0564(2) 0.170(3) Uani 1 1 d G . . H18 H 0.8072 0.2142 -0.0919 0.205 Uiso 1 1 calc R . . C19 C 0.7883(2) 0.2524(2) -0.0226(4) 0.172(3) Uani 1 1 d G . . H19 H 0.7560 0.2677 -0.0350 0.207 Uiso 1 1 calc R . . C20 C 0.6303(4) 0.1040(5) 0.1815(5) 0.267(6) Uani 1 1 d . . . H20A H 0.6160 0.0804 0.2092 0.401 Uiso 1 1 calc R . . H20B H 0.6583 0.0854 0.1617 0.401 Uiso 1 1 calc R . . H20C H 0.6016 0.1142 0.1570 0.401 Uiso 1 1 calc R . . C21 C 0.6208(4) 0.1739(4) 0.2491(4) 0.262(5) Uani 1 1 d . . . H21A H 0.6420 0.1991 0.2701 0.393 Uiso 1 1 calc R . . H21B H 0.6087 0.1447 0.2720 0.393 Uiso 1 1 calc R . . H21C H 0.5899 0.1924 0.2340 0.393 Uiso 1 1 calc R . . C22 C 0.9447(5) 0.1391(4) -0.0519(4) 0.313(7) Uani 1 1 d . . . H22A H 0.9709 0.1660 -0.0412 0.470 Uiso 1 1 calc R . . H22B H 0.9598 0.1167 -0.0802 0.470 Uiso 1 1 calc R . . H22C H 0.9357 0.1168 -0.0211 0.470 Uiso 1 1 calc R . . C23 C 0.8720(3) 0.1443(3) -0.1183(4) 0.195(3) Uani 1 1 d . . . H23A H 0.8369 0.1296 -0.1093 0.292 Uiso 1 1 calc R . . H23B H 0.8947 0.1158 -0.1324 0.292 Uiso 1 1 calc R . . H23C H 0.8680 0.1723 -0.1452 0.292 Uiso 1 1 calc R . . C24 C 0.9291(5) 0.4291(5) 0.0709(5) 0.273(14) Uani 1 3 d SD . . C25 C 0.9589(5) 0.3931(4) 0.0345(3) 0.188(4) Uani 1 1 d G . . C26 C 0.9335(2) 0.3514(5) 0.0082(4) 0.257(6) Uani 1 1 d G . . H26 H 0.8965 0.3454 0.0134 0.308 Uiso 1 1 calc R . . C27 C 0.9624(5) 0.3185(2) -0.0258(3) 0.226(6) Uani 1 1 d G . . H27 H 0.9451 0.2900 -0.0438 0.271 Uiso 1 1 calc R . . C28 C 1.0166(5) 0.3272(3) -0.0335(3) 0.208(6) Uani 1 1 d G . . H28 H 1.0363 0.3047 -0.0567 0.250 Uiso 0.33 1 calc PR . . C29 C 1.0419(2) 0.3689(4) -0.0072(4) 0.201(5) Uani 1 1 d G . . H29 H 1.0790 0.3749 -0.0124 0.241 Uiso 1 1 calc R . . C30 C 1.0131(5) 0.4019(2) 0.0268(3) 0.189(4) Uani 1 1 d G . . H30 H 1.0304 0.4304 0.0448 0.227 Uiso 1 1 calc R . . C31 C 1.0858(7) 0.2966(6) -0.0763(6) 0.240(8) Uani 0.67 1 d P . . H31A H 1.0897 0.3290 -0.0978 0.361 Uiso 0.67 1 calc PR . . H31B H 1.0969 0.2656 -0.0973 0.361 Uiso 0.67 1 calc PR . . H31C H 1.1082 0.2994 -0.0444 0.361 Uiso 0.67 1 calc PR . . C32 C 1.0056(5) 0.2615(6) -0.0988(6) 0.263(9) Uani 0.67 1 d P . . H32A H 0.9941 0.2279 -0.0824 0.395 Uiso 0.67 1 calc PR . . H32B H 1.0276 0.2538 -0.1301 0.395 Uiso 0.67 1 calc PR . . H32C H 0.9742 0.2820 -0.1096 0.395 Uiso 0.67 1 calc PR . . 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 0.148(4) 0.147(4) 0.157(4) -0.019(3) -0.033(3) -0.012(4) O2 0.338(8) 0.338(8) 0.338(8) 0.130(6) 0.130(6) -0.130(6) N1 0.223(8) 0.155(7) 0.257(10) 0.054(7) 0.093(7) 0.050(6) N2 0.194(7) 0.205(7) 0.139(6) -0.009(5) 0.000(5) 0.036(6) N3 0.218(15) 0.228(13) 0.133(9) -0.025(8) 0.046(9) 0.085(12) C1 0.119(6) 0.134(6) 0.131(6) -0.019(5) -0.016(5) -0.020(5) C2 0.129(5) 0.125(7) 0.127(7) 0.002(5) -0.012(5) -0.009(5) C3 0.148(6) 0.151(7) 0.129(7) -0.019(7) -0.004(5) 0.010(6) C4 0.158(7) 0.167(8) 0.126(6) 0.011(7) 0.007(5) 0.002(6) C5 0.156(7) 0.154(10) 0.190(10) 0.052(8) 0.056(7) 0.007(7) C6 0.182(8) 0.150(7) 0.217(10) -0.002(8) 0.074(6) -0.011(6) C7 0.186(8) 0.135(7) 0.170(7) -0.011(7) 0.043(5) -0.024(6) C8 0.154(8) 0.114(6) 0.111(5) -0.001(5) 0.000(5) 0.008(5) C9 0.164(7) 0.118(7) 0.152(6) -0.007(5) 0.015(6) 0.009(7) C10 0.184(9) 0.123(6) 0.170(8) -0.005(6) 0.031(7) -0.002(8) C11 0.207(12) 0.196(11) 0.159(7) 0.009(7) 0.028(8) 0.027(7) C12 0.165(7) 0.200(9) 0.164(7) 0.021(6) -0.034(6) 0.023(8) C13 0.121(6) 0.182(8) 0.156(7) 0.003(6) -0.023(5) -0.015(7) C14 0.100(6) 0.116(5) 0.164(9) 0.004(6) -0.001(5) -0.002(4) C15 0.163(8) 0.149(6) 0.122(6) -0.007(5) -0.010(6) 0.016(5) C16 0.173(7) 0.159(7) 0.125(7) -0.005(5) -0.005(7) 0.025(5) C17 0.150(8) 0.141(6) 0.128(8) -0.011(6) 0.041(6) -0.003(6) C18 0.131(7) 0.231(9) 0.149(7) -0.019(7) -0.002(6) 0.018(6) C19 0.149(7) 0.238(9) 0.130(7) -0.042(6) -0.030(6) 0.011(6) C20 0.247(11) 0.182(9) 0.373(16) 0.097(11) 0.129(11) 0.022(9) C21 0.281(11) 0.256(10) 0.249(10) 0.064(8) 0.145(9) 0.076(9) C22 0.366(14) 0.379(16) 0.196(9) -0.022(9) -0.005(10) 0.234(14) C23 0.211(9) 0.190(8) 0.184(8) -0.032(6) 0.049(7) -0.020(6) C24 0.273(14) 0.273(14) 0.273(14) 0.079(11) 0.079(11) -0.079(11) C25 0.195(10) 0.176(12) 0.193(9) 0.067(8) -0.006(9) -0.070(9) C26 0.256(12) 0.182(11) 0.332(17) 0.064(11) 0.007(12) -0.101(12) C27 0.304(19) 0.130(8) 0.243(13) 0.008(7) -0.049(12) -0.045(10) C28 0.186(11) 0.219(16) 0.219(14) 0.097(13) 0.022(11) 0.039(11) C29 0.252(11) 0.131(8) 0.220(11) 0.032(7) -0.081(10) -0.042(8) C30 0.246(14) 0.126(7) 0.196(9) 0.033(6) -0.015(8) 0.016(8) C31 0.239(16) 0.219(14) 0.262(17) -0.044(12) 0.070(14) 0.099(13) C32 0.199(14) 0.39(2) 0.201(14) -0.159(16) -0.010(11) 0.079(14) _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 C1 1.447(6) . ? O2 C24 1.49(2) . ? N1 C5 1.399(8) . ? N1 C21 1.432(9) . ? N1 C20 1.491(11) . ? N2 C17 1.387(7) . ? N2 C23 1.415(8) . ? N2 C22 1.490(9) . ? N3 C31 1.326(15) . ? N3 C32 1.400(16) . ? C1 C14 1.534(7) . ? C1 C8 1.548(7) . ? C1 C2 1.568(7) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C6 C7 1.3900 . ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? C14 C15 1.3900 . ? C14 C19 1.3900 . ? C15 C16 1.3900 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C18 C19 1.3900 . ? C24 C25 1.485(7) 11_645 ? C24 C25 1.485(7) . ? C24 C25 1.485(7) 12_556 ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C28 C29 1.3900 . ? C29 C30 1.3900 . ? 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 N1 C21 120.6(9) . . ? C5 N1 C20 116.0(9) . . ? C21 N1 C20 113.9(9) . . ? C17 N2 C23 120.1(8) . . ? C17 N2 C22 120.0(8) . . ? C23 N2 C22 116.7(8) . . ? C31 N3 C32 112.6(12) . . ? O1 C1 C14 110.7(6) . . ? O1 C1 C8 107.0(6) . . ? C14 C1 C8 110.3(6) . . ? O1 C1 C2 106.6(6) . . ? C14 C1 C2 111.4(6) . . ? C8 C1 C2 110.7(6) . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 121.0(8) . . ? C7 C2 C1 118.8(8) . . ? C4 C3 C2 120.0 . . ? C3 C4 C5 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 N1 119.2(9) . . ? C6 C5 N1 120.7(9) . . ? C5 C6 C7 120.0 . . ? C6 C7 C2 120.0 . . ? C9 C8 C13 120.0 . . ? C9 C8 C1 118.0(8) . . ? C13 C8 C1 121.9(8) . . ? C10 C9 C8 120.0 . . ? C11 C10 C9 120.0 . . ? C10 C11 C12 120.0 . . ? C13 C12 C11 120.0 . . ? C12 C13 C8 120.0 . . ? C15 C14 C19 120.0 . . ? C15 C14 C1 117.3(7) . . ? C19 C14 C1 122.5(7) . . ? C16 C15 C14 120.0 . . ? C15 C16 C17 120.0 . . ? N2 C17 C18 119.5(8) . . ? N2 C17 C16 120.5(8) . . ? C18 C17 C16 120.0 . . ? C17 C18 C19 120.0 . . ? C18 C19 C14 120.0 . . ? C25 C24 C25 111.7(8) 11_645 . ? C25 C24 C25 111.7(8) 11_645 12_556 ? C25 C24 C25 111.7(8) . 12_556 ? C25 C24 O2 107.1(9) 11_645 . ? C25 C24 O2 107.1(9) . . ? C25 C24 O2 107.1(9) 12_556 . ? C26 C25 C30 120.0 . . ? C26 C25 C24 121.3(12) . . ? C30 C25 C24 118.7(12) . . ? C25 C26 C27 120.0 . . ? C26 C27 C28 120.0 . . ? C29 C28 C27 120.0 . . ? C28 C29 C30 120.0 . . ? C29 C30 C25 120.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O1 0.84 2.23 2.971(10) 146.7 11_645 O2 H2 O1 0.84 2.33 2.827(9) 118.6 11_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 60.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.035 data_SO _database_code_depnum_ccdc_archive 'CCDC 285200' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O' _chemical_formula_weight 303.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5311(8) _cell_length_b 17.5750(10) _cell_length_c 18.4490(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.444(2) _cell_angle_gamma 90.00 _cell_volume 3414.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type 'symmetry related measurements' _exptl_absorpt_correction_T_min 0.652882 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'as implemented in SAINT+/SADABS package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14718 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 22.27 _reflns_number_total 4321 _reflns_number_gt 3038 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; SAINT: SAX, Area Detector Integration, Siemens Analytical instruments INC., Madison, Wisconsin, USA. ; _computing_cell_refinement ; SAINT: SAX, Area Detector Integration, Siemens Analytical instruments INC., Madison, Wisconsin, USA. ; _computing_data_reduction ; SAINT: SAX, Area Detector Integration, Siemens Analytical instruments INC., Madison, Wisconsin, USA. SADABS: Siemens Area Detector Absorption Correction Software, Sheldrick G., 1996, University of Goettingen, Germany. ; _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; PARST - M. Nardelli, J. Appl. Crystallogr. 1995, 28, 659 ; _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^)+(0.0584P)^2^+0.0382P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4321 _refine_ls_number_parameters 584 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 N1 N 0.53456(16) 0.33225(11) 0.00398(10) 0.0658(5) Uani 1 1 d . . . N2 N 1.03214(16) 0.12991(10) 0.38119(10) 0.0574(5) Uani 1 1 d . . . O1 O -0.06470(14) 0.34327(9) 0.03260(9) 0.0663(5) Uani 1 1 d . . . O2 O 0.43685(14) 0.12256(9) 0.34653(9) 0.0598(4) Uani 1 1 d . . . C1 C 0.01005(18) 0.30115(12) 0.08471(11) 0.0502(5) Uani 1 1 d . . . C2 C 0.15042(18) 0.30709(12) 0.06475(10) 0.0482(5) Uani 1 1 d . . . C3 C 0.2021(2) 0.37726(13) 0.04832(12) 0.0556(6) Uani 1 1 d . . . C4 C 0.3276(2) 0.38585(13) 0.02974(12) 0.0565(6) Uani 1 1 d . . . C5 C 0.40887(19) 0.32394(12) 0.02686(11) 0.0507(5) Uani 1 1 d . . . C6 C 0.3581(2) 0.25330(13) 0.04366(12) 0.0558(6) Uani 1 1 d . . . C7 C 0.2317(2) 0.24592(14) 0.06183(12) 0.0541(6) Uani 1 1 d . . . C8 C -0.0167(2) 0.33922(11) 0.15764(11) 0.0508(5) Uani 1 1 d . . . C9 C 0.0764(3) 0.35290(13) 0.20892(13) 0.0632(6) Uani 1 1 d . . . C10 C 0.0478(3) 0.38744(14) 0.27412(15) 0.0741(7) Uani 1 1 d . . . C11 C -0.0746(3) 0.40819(14) 0.28878(16) 0.0726(7) Uani 1 1 d . . . C12 C -0.1689(3) 0.39474(13) 0.23947(15) 0.0696(7) Uani 1 1 d . . . C13 C -0.1408(2) 0.35979(12) 0.17402(14) 0.0601(6) Uani 1 1 d . . . C14 C -0.03375(18) 0.21820(12) 0.08528(12) 0.0514(5) Uani 1 1 d . . . C15 C -0.0339(2) 0.17497(14) 0.14729(14) 0.0634(6) Uani 1 1 d . . . C16 C -0.0668(3) 0.09905(16) 0.14620(18) 0.0777(8) Uani 1 1 d . . . C17 C -0.0997(3) 0.06457(18) 0.08287(19) 0.0848(8) Uani 1 1 d . . . C18 C -0.1022(3) 0.10658(19) 0.02073(19) 0.0891(9) Uani 1 1 d . . . C19 C -0.0697(2) 0.18279(17) 0.02170(15) 0.0724(7) Uani 1 1 d . . . C20 C 0.6193(3) 0.26699(19) 0.0110(2) 0.0763(8) Uani 1 1 d . . . C21 C 0.5955(3) 0.40481(18) 0.0157(2) 0.0795(8) Uani 1 1 d . . . C22 C 0.50954(18) 0.16164(11) 0.29207(11) 0.0488(5) Uani 1 1 d . . . C23 C 0.64989(18) 0.15525(11) 0.31255(10) 0.0463(5) Uani 1 1 d . . . C24 C 0.7314(2) 0.21615(12) 0.31656(11) 0.0509(5) Uani 1 1 d . . . C25 C 0.8572(2) 0.20816(13) 0.33700(11) 0.0522(6) Uani 1 1 d . . . C26 C 0.90746(19) 0.13770(12) 0.35530(10) 0.0477(5) Uani 1 1 d . . . C27 C 0.8257(2) 0.07552(13) 0.35024(12) 0.0560(6) Uani 1 1 d . . . C28 C 0.7002(2) 0.08444(12) 0.32967(12) 0.0547(6) Uani 1 1 d . . . C29 C 0.47960(19) 0.12065(11) 0.22083(11) 0.0497(5) Uani 1 1 d . . . C30 C 0.5692(2) 0.11174(13) 0.16745(12) 0.0576(6) Uani 1 1 d . . . C31 C 0.5391(3) 0.07639(14) 0.10240(14) 0.0697(7) Uani 1 1 d . . . C32 C 0.4195(3) 0.05007(15) 0.09015(16) 0.0776(8) Uani 1 1 d . . . C33 C 0.3296(3) 0.05877(15) 0.14246(17) 0.0804(8) Uani 1 1 d . . . C34 C 0.3584(2) 0.09379(14) 0.20747(15) 0.0673(7) Uani 1 1 d . . . C35 C 0.46765(18) 0.24501(11) 0.28806(11) 0.0493(5) Uani 1 1 d . . . C36 C 0.4252(2) 0.28219(15) 0.34898(15) 0.0663(7) Uani 1 1 d . . . C37 C 0.3980(3) 0.35908(16) 0.34764(17) 0.0811(8) Uani 1 1 d . . . C38 C 0.4113(3) 0.39988(17) 0.28595(17) 0.0820(8) Uani 1 1 d . . . C39 C 0.4509(3) 0.36431(15) 0.22498(16) 0.0801(8) Uani 1 1 d . . . C40 C 0.4788(2) 0.28736(14) 0.22575(14) 0.0682(7) Uani 1 1 d . . . C41 C 1.1216(3) 0.19052(18) 0.36435(19) 0.0723(7) Uani 1 1 d . . . C42 C 1.0882(3) 0.05420(17) 0.3782(2) 0.0797(8) Uani 1 1 d . . . H1O H -0.025(3) 0.3453(15) -0.0079(16) 0.101(11) Uiso 1 1 d . . . H2O H 0.467(2) 0.1357(14) 0.3897(14) 0.090(10) Uiso 1 1 d . . . H3 H 0.1501(18) 0.4197(12) 0.0509(10) 0.056(6) Uiso 1 1 d . . . H4 H 0.3608(19) 0.4372(13) 0.0190(11) 0.070(7) Uiso 1 1 d . . . H6 H 0.4104(18) 0.2076(11) 0.0426(10) 0.055(6) Uiso 1 1 d . . . H7 H 0.2046(17) 0.1960(11) 0.0714(10) 0.050(6) Uiso 1 1 d . . . H9 H 0.163(2) 0.3380(11) 0.1999(11) 0.067(7) Uiso 1 1 d . . . H10 H 0.116(2) 0.3967(14) 0.3060(14) 0.092(9) Uiso 1 1 d . . . H11 H -0.093(2) 0.4314(15) 0.3365(15) 0.101(9) Uiso 1 1 d . . . H12 H -0.262(2) 0.4092(13) 0.2485(13) 0.092(8) Uiso 1 1 d . . . H13 H -0.209(2) 0.3503(12) 0.1375(13) 0.075(7) Uiso 1 1 d . . . H15 H -0.0112(18) 0.2001(11) 0.1930(12) 0.061(6) Uiso 1 1 d . . . H16 H -0.066(2) 0.0727(14) 0.1912(14) 0.089(9) Uiso 1 1 d . . . H17 H -0.130(2) 0.0089(17) 0.0793(15) 0.112(9) Uiso 1 1 d . . . H18 H -0.131(3) 0.0843(17) -0.0251(18) 0.121(11) Uiso 1 1 d . . . H19 H -0.074(2) 0.2141(13) -0.0203(13) 0.074(7) Uiso 1 1 d . . . H24 H 0.7010(17) 0.2675(11) 0.3050(10) 0.055(6) Uiso 1 1 d . . . H25 H 0.9130(19) 0.2530(12) 0.3380(10) 0.061(6) Uiso 1 1 d . . . H27 H 0.8555(18) 0.0248(12) 0.3612(11) 0.062(6) Uiso 1 1 d . . . H28 H 0.640(2) 0.0387(12) 0.3270(11) 0.072(6) Uiso 1 1 d . . . H30 H 0.652(2) 0.1313(10) 0.1751(10) 0.055(6) Uiso 1 1 d . . . H31 H 0.608(2) 0.0725(13) 0.0651(14) 0.094(8) Uiso 1 1 d . . . H32 H 0.402(2) 0.0236(14) 0.0460(15) 0.093(8) Uiso 1 1 d . . . H33 H 0.250(2) 0.0438(13) 0.1357(13) 0.083(8) Uiso 1 1 d . . . H34 H 0.300(2) 0.1026(13) 0.2447(13) 0.084(8) Uiso 1 1 d . . . H36 H 0.415(2) 0.2521(12) 0.3905(13) 0.069(7) Uiso 1 1 d . . . H37 H 0.372(2) 0.3828(15) 0.3924(16) 0.103(9) Uiso 1 1 d . . . H38 H 0.397(2) 0.4525(17) 0.2857(14) 0.107(10) Uiso 1 1 d . . . H39 H 0.464(2) 0.3909(15) 0.1801(16) 0.105(9) Uiso 1 1 d . . . H40 H 0.504(2) 0.2617(12) 0.1829(13) 0.074(7) Uiso 1 1 d . . . H211 H 0.552(3) 0.4436(17) -0.0155(15) 0.111(11) Uiso 1 1 d . . . H212 H 0.677(3) 0.4000(14) 0.0038(13) 0.089(9) Uiso 1 1 d . . . H213 H 0.588(2) 0.4236(14) 0.0684(16) 0.103(10) Uiso 1 1 d . . . H221 H 0.696(3) 0.2803(13) -0.0066(13) 0.084(8) Uiso 1 1 d . . . H222 H 0.586(2) 0.2201(15) -0.0152(13) 0.088(9) Uiso 1 1 d . . . H223 H 0.632(2) 0.2524(14) 0.0628(15) 0.090(9) Uiso 1 1 d . . . H411 H 1.098(2) 0.2371(16) 0.3865(15) 0.096(10) Uiso 1 1 d . . . H412 H 1.208(3) 0.1776(14) 0.3848(14) 0.095(8) Uiso 1 1 d . . . H413 H 1.134(3) 0.1992(16) 0.3135(17) 0.115(11) Uiso 1 1 d . . . H421 H 1.183(2) 0.0603(12) 0.3925(12) 0.077(7) Uiso 1 1 d . . . H422 H 1.085(2) 0.0347(16) 0.3301(16) 0.101(10) Uiso 1 1 d . . . H423 H 1.045(2) 0.0217(16) 0.4138(15) 0.101(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0464(11) 0.0722(13) 0.0789(14) 0.0038(10) 0.0135(10) -0.0037(10) N2 0.0464(11) 0.0620(12) 0.0638(12) -0.0035(9) -0.0016(9) 0.0044(9) O1 0.0510(9) 0.0903(12) 0.0577(11) 0.0193(9) 0.0062(8) 0.0124(8) O2 0.0547(9) 0.0702(10) 0.0548(10) 0.0076(8) 0.0088(8) -0.0068(7) C1 0.0438(12) 0.0595(13) 0.0472(13) 0.0069(11) 0.0032(10) 0.0044(10) C2 0.0465(12) 0.0563(14) 0.0418(12) 0.0051(10) 0.0039(9) 0.0026(11) C3 0.0509(15) 0.0523(14) 0.0638(15) -0.0004(11) 0.0078(11) 0.0058(12) C4 0.0530(15) 0.0530(14) 0.0635(15) 0.0026(11) 0.0080(11) -0.0048(12) C5 0.0454(13) 0.0607(14) 0.0462(13) 0.0029(10) 0.0067(10) -0.0018(11) C6 0.0468(14) 0.0578(15) 0.0628(15) 0.0062(12) 0.0077(11) 0.0080(12) C7 0.0508(14) 0.0517(14) 0.0599(15) 0.0098(11) 0.0064(10) -0.0001(12) C8 0.0514(13) 0.0510(12) 0.0502(13) 0.0058(10) 0.0095(11) 0.0001(10) C9 0.0603(17) 0.0708(16) 0.0584(17) -0.0017(12) 0.0056(13) 0.0026(13) C10 0.081(2) 0.0792(18) 0.0619(18) -0.0097(14) 0.0010(16) -0.0018(15) C11 0.096(2) 0.0591(15) 0.0627(18) -0.0054(13) 0.0219(17) -0.0001(14) C12 0.0720(19) 0.0595(15) 0.078(2) 0.0009(14) 0.0248(16) 0.0036(13) C13 0.0559(15) 0.0630(15) 0.0617(16) 0.0031(12) 0.0109(13) -0.0004(12) C14 0.0409(12) 0.0634(14) 0.0500(14) -0.0024(12) 0.0089(10) -0.0004(10) C15 0.0754(17) 0.0606(16) 0.0542(16) -0.0010(14) 0.0084(13) -0.0055(12) C16 0.093(2) 0.0675(19) 0.073(2) 0.0036(17) 0.0191(16) -0.0072(14) C17 0.084(2) 0.0713(19) 0.099(3) -0.0125(19) 0.0134(17) -0.0147(15) C18 0.102(2) 0.091(2) 0.075(2) -0.0218(19) 0.0004(17) -0.0194(17) C19 0.0764(18) 0.084(2) 0.0572(18) -0.0018(16) 0.0045(13) -0.0122(14) C20 0.0476(16) 0.093(2) 0.089(2) 0.0092(19) 0.0136(15) 0.0068(16) C21 0.0534(18) 0.088(2) 0.097(3) 0.0038(19) 0.0081(17) -0.0150(16) C22 0.0480(12) 0.0521(12) 0.0465(13) 0.0030(10) 0.0065(10) -0.0042(10) C23 0.0460(12) 0.0483(13) 0.0445(12) 0.0009(10) 0.0027(9) -0.0016(10) C24 0.0497(14) 0.0471(14) 0.0560(14) 0.0032(11) 0.0026(10) 0.0020(11) C25 0.0466(14) 0.0509(14) 0.0591(14) 0.0001(11) 0.0054(11) -0.0069(11) C26 0.0468(13) 0.0553(14) 0.0412(12) -0.0030(10) 0.0036(10) 0.0029(11) C27 0.0597(16) 0.0480(14) 0.0601(15) 0.0019(11) -0.0012(11) 0.0042(12) C28 0.0527(15) 0.0514(14) 0.0601(14) 0.0011(11) -0.0005(11) -0.0051(11) C29 0.0503(14) 0.0465(12) 0.0522(13) 0.0012(10) 0.0005(11) -0.0023(10) C30 0.0559(16) 0.0587(14) 0.0583(16) -0.0014(12) 0.0026(13) -0.0014(12) C31 0.0788(19) 0.0704(16) 0.0599(17) -0.0097(13) 0.0028(15) 0.0045(14) C32 0.101(2) 0.0670(17) 0.0643(19) -0.0144(14) -0.0078(18) -0.0043(15) C33 0.073(2) 0.0786(18) 0.089(2) -0.0078(16) -0.0155(18) -0.0226(15) C34 0.0612(17) 0.0733(16) 0.0673(18) -0.0071(14) 0.0014(14) -0.0124(13) C35 0.0454(12) 0.0550(13) 0.0475(13) -0.0030(11) -0.0010(10) 0.0005(10) C36 0.0753(17) 0.0648(17) 0.0587(16) -0.0009(14) 0.0047(13) 0.0049(13) C37 0.103(2) 0.0691(19) 0.071(2) -0.0165(17) 0.0061(16) 0.0158(15) C38 0.103(2) 0.0570(18) 0.086(2) -0.0056(18) -0.0154(17) 0.0120(15) C39 0.116(2) 0.0617(17) 0.0622(19) 0.0042(16) -0.0091(16) 0.0115(15) C40 0.0907(19) 0.0617(16) 0.0523(16) -0.0004(14) 0.0014(13) 0.0103(13) C41 0.0486(16) 0.088(2) 0.080(2) 0.0054(17) 0.0057(15) -0.0060(15) C42 0.0638(19) 0.080(2) 0.095(2) -0.0164(19) -0.0100(18) 0.0202(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.400(3) . ? N1 C21 1.443(3) . ? N1 C20 1.459(3) . ? N2 C26 1.400(2) . ? N2 C42 1.457(3) . ? N2 C41 1.457(3) . ? O1 C1 1.442(2) . ? O2 C22 1.442(2) . ? C1 C14 1.529(3) . ? C1 C2 1.530(3) . ? C1 C8 1.531(3) . ? C2 C7 1.376(3) . ? C2 C3 1.383(3) . ? C3 C4 1.376(3) . ? C4 C5 1.386(3) . ? C5 C6 1.388(3) . ? C6 C7 1.381(3) . ? C8 C9 1.378(3) . ? C8 C13 1.392(3) . ? C9 C10 1.383(3) . ? C10 C11 1.369(4) . ? C11 C12 1.362(4) . ? C12 C13 1.389(3) . ? C14 C15 1.373(3) . ? C14 C19 1.378(3) . ? C15 C16 1.379(3) . ? C16 C17 1.359(4) . ? C17 C18 1.364(4) . ? C18 C19 1.383(4) . ? C22 C23 1.527(3) . ? C22 C29 1.530(3) . ? C22 C35 1.532(3) . ? C23 C24 1.374(3) . ? C23 C28 1.388(3) . ? C24 C25 1.381(3) . ? C25 C26 1.388(3) . ? C26 C27 1.394(3) . ? C27 C28 1.381(3) . ? C29 C30 1.378(3) . ? C29 C34 1.381(3) . ? C30 C31 1.386(3) . ? C31 C32 1.359(4) . ? C32 C33 1.366(4) . ? C33 C34 1.380(4) . ? C35 C40 1.375(3) . ? C35 C36 1.378(3) . ? C36 C37 1.382(3) . ? C37 C38 1.353(4) . ? C38 C39 1.356(4) . ? C39 C40 1.384(3) . ? 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 N1 C21 117.9(2) . . ? C5 N1 C20 118.1(2) . . ? C21 N1 C20 114.2(2) . . ? C26 N2 C42 117.12(19) . . ? C26 N2 C41 117.51(19) . . ? C42 N2 C41 113.4(2) . . ? O1 C1 C14 109.31(16) . . ? O1 C1 C2 109.14(16) . . ? C14 C1 C2 111.03(16) . . ? O1 C1 C8 104.97(16) . . ? C14 C1 C8 110.69(16) . . ? C2 C1 C8 111.50(16) . . ? C7 C2 C3 116.3(2) . . ? C7 C2 C1 123.97(19) . . ? C3 C2 C1 119.77(18) . . ? C4 C3 C2 122.2(2) . . ? C3 C4 C5 121.2(2) . . ? C4 C5 C6 117.04(19) . . ? C4 C5 N1 121.02(19) . . ? C6 C5 N1 121.84(19) . . ? C7 C6 C5 120.8(2) . . ? C2 C7 C6 122.5(2) . . ? C9 C8 C13 118.0(2) . . ? C9 C8 C1 123.01(19) . . ? C13 C8 C1 118.9(2) . . ? C8 C9 C10 121.0(2) . . ? C11 C10 C9 120.1(3) . . ? C12 C11 C10 120.3(3) . . ? C11 C12 C13 119.9(3) . . ? C12 C13 C8 120.7(2) . . ? C15 C14 C19 117.2(2) . . ? C15 C14 C1 122.4(2) . . ? C19 C14 C1 120.4(2) . . ? C14 C15 C16 121.7(3) . . ? C17 C16 C15 120.4(3) . . ? C16 C17 C18 119.0(3) . . ? C17 C18 C19 120.7(3) . . ? C14 C19 C18 121.0(3) . . ? O2 C22 C23 108.10(16) . . ? O2 C22 C29 105.51(16) . . ? C23 C22 C29 111.76(16) . . ? O2 C22 C35 109.58(15) . . ? C23 C22 C35 111.11(15) . . ? C29 C22 C35 110.58(16) . . ? C24 C23 C28 116.68(19) . . ? C24 C23 C22 124.02(18) . . ? C28 C23 C22 119.28(18) . . ? C23 C24 C25 122.2(2) . . ? C24 C25 C26 121.4(2) . . ? C25 C26 C27 116.67(19) . . ? C25 C26 N2 121.69(18) . . ? C27 C26 N2 121.56(19) . . ? C28 C27 C26 121.3(2) . . ? C27 C28 C23 121.8(2) . . ? C30 C29 C34 118.1(2) . . ? C30 C29 C22 122.00(19) . . ? C34 C29 C22 119.89(19) . . ? C29 C30 C31 121.1(2) . . ? C32 C31 C30 120.1(3) . . ? C31 C32 C33 119.4(3) . . ? C32 C33 C34 121.0(3) . . ? C33 C34 C29 120.3(3) . . ? C40 C35 C36 117.1(2) . . ? C40 C35 C22 122.12(19) . . ? C36 C35 C22 120.62(19) . . ? C35 C36 C37 121.2(3) . . ? C38 C37 C36 120.7(3) . . ? C37 C38 C39 119.2(3) . . ? C38 C39 C40 120.6(3) . . ? C35 C40 C39 121.2(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N2 0.86(3) 2.18(3) 3.018(2) 165(3) 4_465 O2 H2O N1 0.88(3) 2.29(3) 3.175(3) 177(2) 4_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.27 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.131 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.029 #===END data_alpha-MG _database_code_depnum_ccdc_archive 'CCDC 285201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 N2 O' _chemical_formula_weight 346.46 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 cubic _symmetry_space_group_name_H-M Pa3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 'z, x, y' 'y, z, x' '-z+1/2, -x, y+1/2' '-y, z+1/2, -x+1/2' 'z+1/2, -x+1/2, -y' '-y+1/2, -z, x+1/2' '-z, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' '-z, -x, -y' '-y, -z, -x' 'z-1/2, x, -y-1/2' 'y, -z-1/2, x-1/2' '-z-1/2, x-1/2, y' 'y-1/2, z, -x-1/2' 'z, -x-1/2, y-1/2' '-y-1/2, z-1/2, x' _cell_length_a 25.390(2) _cell_length_b 25.390(2) _cell_length_c 25.390(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 16368(2) _cell_formula_units_Z 32 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cuboctahedra _exptl_crystal_colour 'pale blue' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5952 _exptl_absorpt_coefficient_mu 0.535 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54138 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3211 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 33.69 _reflns_number_total 1077 _reflns_number_gt 652 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1625P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1077 _refine_ls_number_parameters 283 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.2190 _refine_ls_wR_factor_gt 0.1851 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.011 _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 0.8042(5) 0.3255(4) 0.1037(5) 0.179(3) Uani 1 1 d D . . H1 H 0.8242 0.3071 0.1211 0.26(12) Uiso 1 1 calc RD . . O2 O 0.8953(4) 0.3953(4) 0.1047(4) 0.301(8) Uani 1 3 d SD . . H2 H 0.9126 0.3843 0.1297 0.200 Uiso 0.33 1 calc PRD . . N1 N 0.6496(7) 0.1546(7) 0.2062(9) 0.269(8) Uani 1 1 d . . . N2 N 0.8924(7) 0.1656(6) -0.0663(7) 0.226(5) Uani 1 1 d . . . N3 N 1.0335(14) 0.2924(12) -0.0625(10) 0.249(12) Uani 0.67 1 d P . . C1 C 0.7692(7) 0.2919(7) 0.0732(8) 0.152(4) Uani 1 1 d D . . C2 C 0.7394(4) 0.2548(9) 0.1123(7) 0.150(5) Uani 1 1 d G . . C3 C 0.7180(6) 0.2712(5) 0.1600(9) 0.186(9) Uani 1 1 d G . . H3 H 0.7239 0.3053 0.1719 0.223 Uiso 1 1 calc R . . C4 C 0.6878(5) 0.2366(10) 0.1898(4) 0.201(8) Uani 1 1 d G . . H4 H 0.6734 0.2476 0.2216 0.241 Uiso 1 1 calc R . . C5 C 0.6790(5) 0.1856(8) 0.1719(9) 0.209(8) Uani 1 1 d G . . C6 C 0.7004(8) 0.1692(6) 0.1243(10) 0.230(8) Uani 1 1 d G . . H6 H 0.6945 0.1350 0.1124 0.276 Uiso 1 1 calc R . . C7 C 0.7306(7) 0.2038(11) 0.0945(5) 0.198(6) Uani 1 1 d G . . H7 H 0.7450 0.1928 0.0627 0.238 Uiso 1 1 calc R . . C8 C 0.7315(9) 0.3287(9) 0.0415(3) 0.151(5) Uani 1 1 d G . . C9 C 0.7504(4) 0.3775(11) 0.0253(6) 0.176(5) Uani 1 1 d G . . H9 H 0.7846 0.3876 0.0337 0.211 Uiso 1 1 calc R . . C10 C 0.7183(10) 0.4111(4) -0.0035(6) 0.205(7) Uani 1 1 d G . . H10 H 0.7309 0.4437 -0.0144 0.246 Uiso 1 1 calc R . . C11 C 0.6672(9) 0.3960(8) -0.0161(3) 0.252(10) Uani 1 1 d G . . H11 H 0.6456 0.4185 -0.0354 0.303 Uiso 1 1 calc R . . C12 C 0.6482(4) 0.3473(10) 0.0002(6) 0.248(9) Uani 1 1 d G . . H12 H 0.6140 0.3372 -0.0083 0.298 Uiso 1 1 calc R . . C13 C 0.6804(11) 0.3137(4) 0.0290(6) 0.198(7) Uani 1 1 d G . . H13 H 0.6677 0.2811 0.0399 0.237 Uiso 1 1 calc R . . C14 C 0.8022(8) 0.2615(4) 0.0305(8) 0.158(8) Uani 1 1 d G . . C15 C 0.8488(10) 0.2401(7) 0.0494(5) 0.167(6) Uani 1 1 d G . . H15 H 0.8596 0.2470 0.0838 0.200 Uiso 1 1 calc R . . C16 C 0.8795(5) 0.2083(7) 0.0170(10) 0.177(5) Uani 1 1 d G . . H16 H 0.9107 0.1940 0.0297 0.212 Uiso 1 1 calc R . . C17 C 0.8634(8) 0.1981(4) -0.0343(9) 0.171(6) Uani 1 1 d G . . C18 C 0.8167(9) 0.2195(7) -0.0532(5) 0.223(8) Uani 1 1 d G . . H18 H 0.8060 0.2126 -0.0875 0.267 Uiso 1 1 calc R . . C19 C 0.7861(4) 0.2512(6) -0.0208(10) 0.212(7) Uani 1 1 d G . . H19 H 0.7549 0.2656 -0.0334 0.254 Uiso 1 1 calc R . . C20 C 0.6299(7) 0.1054(8) 0.1822(9) 0.344(12) Uani 1 1 d . . . H20A H 0.6158 0.0829 0.2091 0.517 Uiso 1 1 calc R . . H20B H 0.6583 0.0877 0.1646 0.517 Uiso 1 1 calc R . . H20C H 0.6027 0.1135 0.1571 0.517 Uiso 1 1 calc R . . C21 C 0.6204(8) 0.1749(8) 0.2488(8) 0.342(12) Uani 1 1 d . . . H21A H 0.6414 0.2002 0.2676 0.513 Uiso 1 1 calc R . . H21B H 0.6108 0.1468 0.2721 0.513 Uiso 1 1 calc R . . H21C H 0.5891 0.1917 0.2358 0.513 Uiso 1 1 calc R . . C22 C 0.9430(9) 0.1411(7) -0.0489(7) 0.338(11) Uani 1 1 d . . . H22A H 0.9675 0.1682 -0.0392 0.506 Uiso 1 1 calc R . . H22B H 0.9574 0.1205 -0.0771 0.506 Uiso 1 1 calc R . . H22C H 0.9366 0.1187 -0.0190 0.506 Uiso 1 1 calc R . . C23 C 0.8718(7) 0.1468(5) -0.1148(7) 0.255(7) Uani 1 1 d . . . H23A H 0.8345 0.1418 -0.1115 0.382 Uiso 1 1 calc R . . H23B H 0.8883 0.1139 -0.1235 0.382 Uiso 1 1 calc R . . H23C H 0.8788 0.1721 -0.1421 0.382 Uiso 1 1 calc R . . C24 C 0.9303(5) 0.4303(5) 0.0697(5) 0.219(12) Uani 1 3 d SD . . C25 C 0.9590(11) 0.3913(7) 0.0352(4) 0.187(5) Uani 1 1 d G . . C26 C 0.9342(4) 0.3500(10) 0.0091(8) 0.242(9) Uani 1 1 d G . . H26 H 0.8986 0.3436 0.0146 0.290 Uiso 1 1 calc R . . C27 C 0.9627(10) 0.3183(5) -0.0253(6) 0.249(11) Uani 1 1 d G . . H27 H 0.9461 0.2907 -0.0427 0.298 Uiso 1 1 calc R . . C28 C 1.0160(9) 0.3279(7) -0.0336(5) 0.235(11) Uani 1 1 d G . . H28 H 1.0350 0.3067 -0.0566 0.282 Uiso 0.33 1 calc PR . . C29 C 1.0407(4) 0.3692(9) -0.0075(8) 0.240(10) Uani 1 1 d G . . H29 H 1.0764 0.3756 -0.0130 0.288 Uiso 1 1 calc R . . C30 C 1.0122(11) 0.4009(4) 0.0269(6) 0.214(7) Uani 1 1 d G . . H30 H 1.0288 0.4285 0.0444 0.257 Uiso 1 1 calc R . . C31 C 1.0853(12) 0.3000(11) -0.0748(11) 0.306(16) Uani 0.67 1 d P . . H31A H 1.0950 0.3357 -0.0670 0.459 Uiso 0.67 1 calc PR . . H31B H 1.0906 0.2933 -0.1116 0.459 Uiso 0.67 1 calc PR . . H31C H 1.1067 0.2764 -0.0545 0.459 Uiso 0.67 1 calc PR . . C32 C 1.0064(11) 0.2604(12) -0.0961(12) 0.312(18) Uani 0.67 1 d P . . H32A H 0.9993 0.2274 -0.0790 0.469 Uiso 0.67 1 calc PR . . H32B H 1.0271 0.2543 -0.1271 0.469 Uiso 0.67 1 calc PR . . H32C H 0.9738 0.2770 -0.1057 0.469 Uiso 0.67 1 calc PR . . 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 0.185(7) 0.177(6) 0.174(7) -0.023(8) -0.028(6) -0.024(8) O2 0.301(8) 0.301(8) 0.301(8) 0.093(9) 0.093(9) -0.093(9) N1 0.281(17) 0.191(16) 0.33(2) 0.090(16) 0.120(14) 0.006(12) N2 0.256(16) 0.251(15) 0.170(14) -0.035(11) 0.013(12) 0.023(12) N3 0.28(4) 0.26(3) 0.21(2) -0.036(17) 0.09(2) 0.07(3) C1 0.149(14) 0.147(14) 0.161(15) -0.031(13) -0.016(11) -0.002(11) C2 0.161(11) 0.113(14) 0.18(2) 0.040(14) -0.025(15) -0.039(11) C3 0.184(13) 0.25(2) 0.126(11) -0.074(16) 0.012(10) 0.035(15) C4 0.174(13) 0.28(2) 0.152(12) 0.054(17) 0.038(9) -0.016(13) C5 0.219(18) 0.144(17) 0.26(3) 0.030(18) 0.032(17) -0.003(16) C6 0.238(17) 0.184(19) 0.27(2) -0.028(17) 0.074(13) -0.033(14) C7 0.221(16) 0.162(19) 0.212(15) -0.002(16) 0.060(10) -0.042(11) C8 0.19(2) 0.131(15) 0.131(10) 0.006(11) 0.011(12) 0.002(12) C9 0.199(14) 0.148(16) 0.180(14) -0.003(9) 0.023(13) 0.002(18) C10 0.25(2) 0.163(12) 0.204(17) 0.000(12) 0.023(13) 0.025(18) C11 0.27(3) 0.31(3) 0.184(12) -0.014(16) 0.002(17) 0.068(16) C12 0.221(15) 0.31(3) 0.210(17) 0.032(14) -0.051(13) 0.04(2) C13 0.142(12) 0.258(19) 0.194(15) 0.005(13) -0.035(10) -0.036(17) C14 0.114(12) 0.139(11) 0.22(3) 0.026(15) -0.020(15) 0.004(10) C15 0.21(2) 0.170(12) 0.116(11) -0.032(11) 0.016(16) -0.014(11) C16 0.205(14) 0.200(15) 0.125(14) -0.009(10) 0.015(16) 0.011(13) C17 0.21(2) 0.166(13) 0.14(2) -0.043(13) 0.068(14) -0.006(14) C18 0.182(14) 0.273(18) 0.213(17) -0.029(15) -0.018(17) 0.041(12) C19 0.199(14) 0.274(18) 0.161(13) -0.053(11) -0.046(14) 0.014(13) C20 0.34(2) 0.207(17) 0.48(3) 0.11(2) 0.17(2) -0.002(16) C21 0.37(2) 0.33(2) 0.32(2) 0.081(17) 0.196(19) 0.055(17) C22 0.38(2) 0.35(2) 0.276(19) -0.044(15) 0.034(19) 0.18(2) C23 0.305(18) 0.246(16) 0.213(15) -0.069(13) 0.061(15) 0.001(12) C24 0.219(12) 0.219(12) 0.219(12) 0.075(12) 0.075(12) -0.075(12) C25 0.21(2) 0.149(19) 0.197(14) 0.028(13) 0.026(13) -0.037(13) C26 0.274(18) 0.164(17) 0.29(2) 0.018(14) 0.004(19) -0.09(2) C27 0.35(4) 0.153(12) 0.24(2) -0.017(11) -0.028(18) -0.011(19) C28 0.178(16) 0.30(3) 0.23(3) 0.09(2) 0.015(19) 0.03(2) C29 0.29(2) 0.23(2) 0.207(17) 0.015(12) -0.047(17) -0.032(17) C30 0.24(2) 0.196(16) 0.206(16) 0.040(14) 0.011(13) -0.050(18) C31 0.31(3) 0.28(3) 0.32(3) -0.02(2) 0.12(3) 0.10(3) C32 0.27(3) 0.40(4) 0.27(3) -0.16(3) 0.03(2) 0.07(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.454(12) . ? O2 C24 1.54(2) . ? N1 C5 1.391(15) . ? N1 C21 1.409(18) . ? N1 C20 1.48(2) . ? N2 C17 1.371(15) . ? N2 C23 1.419(16) . ? N2 C22 1.496(18) . ? N3 C31 1.37(3) . ? N3 C32 1.36(3) . ? C1 C8 1.561(14) . ? C1 C2 1.565(15) . ? C1 C14 1.571(14) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C6 C7 1.3900 . ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? C14 C15 1.3900 . ? C14 C19 1.3900 . ? C15 C16 1.3900 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C18 C19 1.3900 . ? C24 C25 1.509(11) . ? C24 C25 1.509(11) 11_645 ? C24 C25 1.509(11) 12_556 ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C28 C29 1.3900 . ? C29 C30 1.3900 . ? 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 N1 C21 124(2) . . ? C5 N1 C20 114(2) . . ? C21 N1 C20 116.7(19) . . ? C17 N2 C23 121.3(17) . . ? C17 N2 C22 122.4(15) . . ? C23 N2 C22 115.6(18) . . ? C31 N3 C32 115(3) . . ? O1 C1 C8 107.3(16) . . ? O1 C1 C2 108.1(16) . . ? C8 C1 C2 113.1(15) . . ? O1 C1 C14 109.3(13) . . ? C8 C1 C14 105.4(16) . . ? C2 C1 C14 113.5(12) . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 124(2) . . ? C7 C2 C1 116(2) . . ? C4 C3 C2 120.0 . . ? C3 C4 C5 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 N1 114(2) . . ? C6 C5 N1 126(2) . . ? C7 C6 C5 120.0 . . ? C6 C7 C2 120.0 . . ? C9 C8 C13 120.0 . . ? C9 C8 C1 118(2) . . ? C13 C8 C1 122(2) . . ? C8 C9 C10 120.0 . . ? C11 C10 C9 120.0 . . ? C10 C11 C12 120.0 . . ? C11 C12 C13 120.0 . . ? C12 C13 C8 120.0 . . ? C15 C14 C19 120.0 . . ? C15 C14 C1 114(2) . . ? C19 C14 C1 126(2) . . ? C14 C15 C16 120.0 . . ? C15 C16 C17 120.0 . . ? N2 C17 C18 119(2) . . ? N2 C17 C16 121(2) . . ? C18 C17 C16 120.0 . . ? C19 C18 C17 120.0 . . ? C18 C19 C14 120.0 . . ? C25 C24 C25 114.7(9) . 11_645 ? C25 C24 C25 114.7(9) . 12_556 ? C25 C24 C25 114.7(9) 11_645 12_556 ? C25 C24 O2 103.5(12) . . ? C25 C24 O2 103.5(12) 11_645 . ? C25 C24 O2 103.5(12) 12_556 . ? C26 C25 C30 120.0 . . ? C26 C25 C24 124(2) . . ? C30 C25 C24 116(2) . . ? C25 C26 C27 120.0 . . ? C26 C27 C28 120.0 . . ? C29 C28 C27 120.0 . . ? C28 C29 C30 120.0 . . ? C29 C30 C25 120.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O1 0.82 2.28 3.00(2) 146.9 11_645 O2 H2 O1 0.82 2.37 2.914(16) 124.8 11_645 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 33.69 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.128 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.028 #===END data_beta-MG _database_code_depnum_ccdc_archive 'CCDC 285202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 N2 O' _chemical_formula_weight 346.46 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.087(4) _cell_length_b 16.628(5) _cell_length_c 10.264(8) _cell_angle_alpha 96.19(6) _cell_angle_beta 95.70(6) _cell_angle_gamma 107.22(3) _cell_volume 1940.1(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour 'pale blue-green' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54138 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5762 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1642 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 59.99 _reflns_number_total 5762 _reflns_number_gt 1801 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5762 _refine_ls_number_parameters 546 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1680 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 0.715 _refine_ls_restrained_S_all 0.715 _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 N1 N 0.9067(3) 0.4723(2) -0.3101(3) 0.0593(11) Uani 1 1 d . . . N2 N 0.7329(3) 0.0895(2) 0.3628(4) 0.0614(11) Uani 1 1 d . . . N3 N 0.7609(4) -0.2437(3) 0.5455(4) 0.0787(13) Uani 1 1 d . . . N4 N 0.4163(4) 0.1720(3) 0.8781(4) 0.0827(14) Uani 1 1 d . . . O1 O 0.8348(3) 0.4798(2) 0.2995(3) 0.0599(9) Uani 1 1 d . . . O2 O 0.8789(3) 0.1559(2) 0.6308(4) 0.0648(10) Uani 1 1 d . . . C1 C 0.7550(4) 0.4155(3) 0.1983(4) 0.0524(12) Uani 1 1 d . . . C2 C 0.7997(4) 0.4267(3) 0.0637(4) 0.0480(12) Uani 1 1 d . . . C3 C 0.7864(4) 0.3603(3) -0.0335(5) 0.0628(14) Uani 1 1 d . . . C4 C 0.8216(4) 0.3740(3) -0.1574(5) 0.0608(14) Uani 1 1 d . . . C5 C 0.8694(4) 0.4548(3) -0.1842(4) 0.0518(12) Uani 1 1 d . . . C6 C 0.8846(4) 0.5232(3) -0.0859(5) 0.0534(13) Uani 1 1 d . . . C7 C 0.8489(4) 0.5087(3) 0.0368(5) 0.0531(13) Uani 1 1 d . . . C8 C 0.7440(4) 0.3273(3) 0.2371(4) 0.0508(12) Uani 1 1 d . . . C9 C 0.6495(4) 0.2789(3) 0.2866(5) 0.0621(14) Uani 1 1 d . . . C10 C 0.6444(4) 0.2009(3) 0.3271(4) 0.0651(14) Uani 1 1 d . . . H10 H 0.5780 0.1706 0.3601 0.078 Uiso 1 1 calc R . . C11 C 0.7352(4) 0.1678(3) 0.3193(4) 0.0527(12) Uani 1 1 d . . . C12 C 0.8326(4) 0.2164(3) 0.2698(4) 0.0643(14) Uani 1 1 d . . . H12 H 0.8959 0.1961 0.2621 0.077 Uiso 1 1 calc R . . C13 C 0.8365(4) 0.2936(3) 0.2324(5) 0.0673(15) Uani 1 1 d . . . C14 C 0.6380(4) 0.4341(3) 0.1944(5) 0.0554(13) Uani 1 1 d . . . C15 C 0.6162(4) 0.4882(3) 0.2901(5) 0.0864(18) Uani 1 1 d . . . H15 H 0.6735 0.5153 0.3616 0.104 Uiso 1 1 calc R . . C16 C 0.5086(5) 0.5035(4) 0.2820(6) 0.104(2) Uani 1 1 d . . . H16 H 0.4958 0.5408 0.3489 0.125 Uiso 1 1 calc R . . C17 C 0.4218(6) 0.4659(4) 0.1797(7) 0.089(2) Uani 1 1 d . . . C18 C 0.4435(5) 0.4111(4) 0.0828(5) 0.0900(18) Uani 1 1 d . . . H18 H 0.3859 0.3844 0.0114 0.108 Uiso 1 1 calc R . . C19 C 0.5501(4) 0.3949(3) 0.0900(5) 0.0771(16) Uani 1 1 d . . . H19 H 0.5625 0.3572 0.0236 0.093 Uiso 1 1 calc R . . C20 C 0.8884(4) 0.3956(3) -0.4061(4) 0.0820(16) Uani 1 1 d . . . H20A H 0.9149 0.4119 -0.4874 0.123 Uiso 1 1 calc R . . H20B H 0.8067 0.3639 -0.4227 0.123 Uiso 1 1 calc R . . H20C H 0.9317 0.3609 -0.3710 0.123 Uiso 1 1 calc R . . C21 C 0.8588(4) 0.5340(3) -0.3690(4) 0.0874(17) Uani 1 1 d . . . H21A H 0.8868 0.5429 -0.4523 0.131 Uiso 1 1 calc R . . H21B H 0.8835 0.5870 -0.3104 0.131 Uiso 1 1 calc R . . H21C H 0.7750 0.5123 -0.3828 0.131 Uiso 1 1 calc R . . C22 C 0.6175(4) 0.0331(3) 0.3785(4) 0.0796(16) Uani 1 1 d . . . H22A H 0.6257 -0.0180 0.4080 0.119 Uiso 1 1 calc R . . H22B H 0.5675 0.0188 0.2952 0.119 Uiso 1 1 calc R . . H22C H 0.5838 0.0614 0.4427 0.119 Uiso 1 1 calc R . . C23 C 0.7984(4) 0.0408(3) 0.2951(5) 0.0853(17) Uani 1 1 d . . . H23A H 0.7650 0.0242 0.2037 0.128 Uiso 1 1 calc R . . H23B H 0.7947 -0.0091 0.3359 0.128 Uiso 1 1 calc R . . H23C H 0.8785 0.0752 0.3012 0.128 Uiso 1 1 calc R . . C24 C 0.8364(4) 0.1094(3) 0.7364(4) 0.0521(12) Uani 1 1 d . . . C25 C 0.9378(4) 0.1435(3) 0.8524(4) 0.0574(13) Uani 1 1 d . . . C26 C 0.9509(4) 0.0943(3) 0.9499(5) 0.0649(14) Uani 1 1 d . . . H26 H 0.9022 0.0385 0.9419 0.078 Uiso 1 1 calc R . . C27 C 1.0355(5) 0.1272(4) 1.0588(5) 0.0748(16) Uani 1 1 d . . . H27 H 1.0424 0.0937 1.1243 0.090 Uiso 1 1 calc R . . C28 C 1.1095(5) 0.2088(4) 1.0712(6) 0.0751(17) Uani 1 1 d . . . C29 C 1.0994(5) 0.2583(4) 0.9740(6) 0.0748(17) Uani 1 1 d . . . C30 C 1.0129(5) 0.2258(3) 0.8666(5) 0.0625(14) Uani 1 1 d . . . C31 C 0.8123(4) 0.0147(3) 0.6892(4) 0.0493(12) Uani 1 1 d . . . C32 C 0.8965(4) -0.0126(3) 0.6311(5) 0.0601(14) Uani 1 1 d . . . C33 C 0.8797(5) -0.0970(4) 0.5833(5) 0.0631(15) Uani 1 1 d . . . C34 C 0.7775(4) -0.1597(3) 0.5924(4) 0.0570(13) Uani 1 1 d . . . C35 C 0.6930(4) -0.1323(3) 0.6505(5) 0.0645(14) Uani 1 1 d . . . C36 C 0.7105(4) -0.0481(3) 0.6971(5) 0.0609(14) Uani 1 1 d . . . C37 C 0.7281(4) 0.1300(3) 0.7773(4) 0.0527(12) Uani 1 1 d . . . C38 C 0.6865(4) 0.1115(3) 0.8959(4) 0.0640(14) Uani 1 1 d . . . H38 H 0.7282 0.0883 0.9541 0.077 Uiso 1 1 calc R . . C39 C 0.5872(5) 0.1261(3) 0.9304(5) 0.0654(15) Uani 1 1 d . . . C40 C 0.5197(4) 0.1603(3) 0.8478(5) 0.0641(14) Uani 1 1 d . . . C41 C 0.5625(5) 0.1815(3) 0.7290(5) 0.0614(14) Uani 1 1 d . . . C42 C 0.6630(4) 0.1666(3) 0.6969(5) 0.0581(13) Uani 1 1 d . . . C43 C 0.8455(5) -0.2690(3) 0.4766(5) 0.0989(19) Uani 1 1 d . . . H43A H 0.8189 -0.3297 0.4514 0.148 Uiso 1 1 calc R . . H43B H 0.9189 -0.2527 0.5335 0.148 Uiso 1 1 calc R . . H43C H 0.8553 -0.2417 0.3989 0.148 Uiso 1 1 calc R . . C44 C 0.6575(4) -0.3080(3) 0.5643(5) 0.0975(19) Uani 1 1 d . . . H44A H 0.6597 -0.3626 0.5258 0.146 Uiso 1 1 calc R . . H44B H 0.5901 -0.2968 0.5225 0.146 Uiso 1 1 calc R . . H44C H 0.6533 -0.3077 0.6573 0.146 Uiso 1 1 calc R . . C45 C 0.3511(4) 0.2096(3) 0.7920(5) 0.101(2) Uani 1 1 d . . . H45A H 0.2822 0.2128 0.8287 0.152 Uiso 1 1 calc R . . H45B H 0.3288 0.1752 0.7066 0.152 Uiso 1 1 calc R . . H45C H 0.3986 0.2657 0.7833 0.152 Uiso 1 1 calc R . . C46 C 0.3759(4) 0.1512(3) 1.0014(5) 0.0996(19) Uani 1 1 d . . . H46A H 0.3034 0.1632 1.0072 0.149 Uiso 1 1 calc R . . H46B H 0.4332 0.1848 1.0738 0.149 Uiso 1 1 calc R . . H46C H 0.3643 0.0920 1.0055 0.149 Uiso 1 1 calc R . . H3 H 0.749(3) 0.298(2) -0.026(3) 0.037(10) Uiso 1 1 d . . . H4 H 0.810(3) 0.319(2) -0.222(3) 0.040(11) Uiso 1 1 d . . . H6 H 0.918(3) 0.586(2) -0.099(3) 0.041(11) Uiso 1 1 d . . . H7 H 0.858(3) 0.560(2) 0.099(3) 0.036(11) Uiso 1 1 d . . . H9 H 0.590(3) 0.302(2) 0.305(3) 0.051(13) Uiso 1 1 d . . . H13 H 0.905(3) 0.324(2) 0.203(4) 0.065(14) Uiso 1 1 d . . . H17 H 0.350(5) 0.483(3) 0.176(5) 0.15(3) Uiso 1 1 d . . . H28 H 1.169(4) 0.239(3) 1.144(4) 0.097(19) Uiso 1 1 d . . . H29 H 1.148(4) 0.319(3) 0.981(4) 0.095(19) Uiso 1 1 d . . . H30 H 1.009(3) 0.264(2) 0.805(4) 0.059(14) Uiso 1 1 d . . . H32 H 0.967(3) 0.032(2) 0.626(3) 0.051(13) Uiso 1 1 d . . . H33 H 0.942(3) -0.109(2) 0.552(3) 0.041(12) Uiso 1 1 d . . . H35 H 0.617(3) -0.176(2) 0.665(3) 0.066(14) Uiso 1 1 d . . . H36 H 0.648(3) -0.033(2) 0.744(4) 0.075(15) Uiso 1 1 d . . . H39 H 0.558(3) 0.110(2) 1.013(4) 0.066(14) Uiso 1 1 d . . . H42 H 0.690(3) 0.182(2) 0.615(3) 0.042(12) Uiso 1 1 d . . . H41 H 0.521(3) 0.210(2) 0.673(4) 0.061(14) Uiso 1 1 d . . . H1O2 H 0.836(3) 0.137(3) 0.568(4) 0.050(17) Uiso 1 1 d . . . H1O1 H 0.910(4) 0.481(3) 0.288(4) 0.080(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.062(3) 0.075(3) 0.042(2) 0.016(2) 0.010(2) 0.020(2) N2 0.065(3) 0.056(3) 0.063(3) 0.015(2) 0.006(2) 0.017(2) N3 0.086(4) 0.054(3) 0.096(4) 0.008(3) 0.030(3) 0.017(3) N4 0.073(3) 0.112(4) 0.079(3) 0.019(3) 0.016(3) 0.049(3) O1 0.057(2) 0.073(2) 0.044(2) 0.0068(17) 0.0057(18) 0.013(2) O2 0.064(3) 0.072(3) 0.054(3) 0.021(2) 0.007(2) 0.010(2) C1 0.053(3) 0.061(3) 0.041(3) 0.007(3) 0.006(2) 0.015(3) C2 0.050(3) 0.048(3) 0.043(3) 0.009(2) 0.005(2) 0.012(2) C3 0.072(4) 0.048(3) 0.055(3) 0.010(3) 0.006(3) -0.001(3) C4 0.071(4) 0.050(3) 0.049(3) -0.002(3) 0.011(3) 0.002(3) C5 0.047(3) 0.063(3) 0.044(3) 0.011(3) 0.003(2) 0.016(3) C6 0.063(3) 0.051(3) 0.049(3) 0.017(3) 0.011(3) 0.017(3) C7 0.059(3) 0.054(3) 0.046(3) 0.003(3) 0.008(2) 0.017(3) C8 0.053(3) 0.055(3) 0.045(3) 0.017(2) 0.008(2) 0.013(3) C9 0.050(3) 0.079(4) 0.067(4) 0.023(3) 0.016(3) 0.028(3) C10 0.054(3) 0.074(4) 0.075(4) 0.040(3) 0.020(3) 0.017(3) C11 0.057(3) 0.056(3) 0.042(3) 0.010(2) 0.004(2) 0.012(3) C12 0.061(3) 0.067(4) 0.075(4) 0.028(3) 0.019(3) 0.028(3) C13 0.049(4) 0.075(4) 0.079(4) 0.026(3) 0.022(3) 0.012(3) C14 0.056(3) 0.064(3) 0.047(3) 0.012(3) 0.011(3) 0.018(3) C15 0.068(4) 0.107(5) 0.085(4) -0.015(4) -0.005(3) 0.043(4) C16 0.087(5) 0.119(6) 0.108(5) -0.017(4) 0.005(4) 0.049(4) C17 0.068(5) 0.114(6) 0.101(5) 0.033(4) 0.020(4) 0.043(4) C18 0.064(4) 0.133(6) 0.073(4) 0.012(4) -0.004(3) 0.036(4) C19 0.064(4) 0.110(5) 0.059(4) 0.007(3) 0.004(3) 0.033(3) C20 0.107(4) 0.094(4) 0.041(3) 0.002(3) 0.016(3) 0.025(3) C21 0.107(5) 0.118(5) 0.060(4) 0.042(3) 0.030(3) 0.055(4) C22 0.072(4) 0.068(4) 0.087(4) 0.015(3) 0.003(3) 0.004(3) C23 0.089(4) 0.083(4) 0.091(4) 0.023(3) 0.011(3) 0.033(3) C24 0.053(3) 0.059(3) 0.045(3) 0.017(2) 0.012(2) 0.013(3) C25 0.054(3) 0.061(3) 0.059(3) 0.011(3) 0.007(3) 0.018(3) C26 0.071(4) 0.062(3) 0.063(4) 0.020(3) 0.005(3) 0.020(3) C27 0.086(4) 0.098(5) 0.049(3) 0.017(3) -0.002(3) 0.043(4) C28 0.069(4) 0.088(5) 0.069(4) -0.006(4) -0.008(4) 0.036(4) C29 0.060(4) 0.068(4) 0.093(5) 0.004(4) -0.006(3) 0.023(3) C30 0.067(4) 0.057(4) 0.065(4) 0.013(3) 0.004(3) 0.021(3) C31 0.052(3) 0.055(3) 0.043(3) 0.014(2) 0.006(2) 0.017(3) C32 0.051(4) 0.060(4) 0.064(3) 0.019(3) 0.017(3) 0.004(3) C33 0.066(4) 0.070(4) 0.063(4) 0.015(3) 0.024(3) 0.030(3) C34 0.065(4) 0.056(3) 0.046(3) 0.007(3) 0.004(3) 0.014(3) C35 0.051(3) 0.060(4) 0.077(4) 0.010(3) 0.014(3) 0.009(3) C36 0.053(4) 0.062(4) 0.068(4) 0.009(3) 0.018(3) 0.015(3) C37 0.053(3) 0.050(3) 0.054(3) 0.008(2) 0.004(3) 0.016(3) C38 0.073(4) 0.074(4) 0.056(3) 0.016(3) 0.009(3) 0.037(3) C39 0.069(4) 0.084(4) 0.050(4) 0.013(3) 0.018(3) 0.032(3) C40 0.059(4) 0.065(4) 0.068(4) 0.001(3) 0.005(3) 0.023(3) C41 0.062(4) 0.063(4) 0.063(4) 0.012(3) -0.001(3) 0.027(3) C42 0.069(4) 0.055(3) 0.048(3) 0.007(3) 0.008(3) 0.017(3) C43 0.108(5) 0.078(4) 0.122(5) 0.008(4) 0.035(4) 0.041(4) C44 0.096(5) 0.066(4) 0.124(5) 0.012(4) 0.028(4) 0.012(4) C45 0.101(5) 0.134(5) 0.094(5) 0.018(4) 0.014(4) 0.074(4) C46 0.079(4) 0.141(6) 0.092(5) 0.024(4) 0.026(4) 0.048(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 N1 C5 1.441(5) . ? N1 C20 1.472(5) . ? N1 C21 1.472(5) . ? N2 C11 1.415(5) . ? N2 C23 1.460(5) . ? N2 C22 1.468(5) . ? N3 C34 1.376(5) . ? N3 C44 1.429(5) . ? N3 C43 1.434(5) . ? N4 C40 1.380(5) . ? N4 C45 1.437(5) . ? N4 C46 1.441(5) . ? O1 C1 1.450(5) . ? O2 C24 1.446(5) . ? C1 C14 1.532(5) . ? C1 C8 1.532(5) . ? C1 C2 1.543(5) . ? C2 C3 1.366(5) . ? C2 C7 1.386(5) . ? C3 C4 1.400(6) . ? C4 C5 1.366(5) . ? C5 C6 1.392(5) . ? C6 C7 1.394(5) . ? C8 C9 1.367(6) . ? C8 C13 1.394(6) . ? C9 C10 1.390(6) . ? C10 C11 1.371(5) . ? C11 C12 1.394(5) . ? C12 C13 1.367(6) . ? C14 C15 1.359(6) . ? C14 C19 1.384(6) . ? C15 C16 1.393(6) . ? C16 C17 1.359(7) . ? C17 C18 1.374(7) . ? C18 C19 1.388(6) . ? C24 C31 1.528(5) . ? C24 C37 1.532(5) . ? C24 C25 1.548(6) . ? C25 C30 1.383(6) . ? C25 C26 1.386(5) . ? C26 C27 1.380(6) . ? C27 C28 1.370(7) . ? C28 C29 1.380(7) . ? C29 C30 1.381(6) . ? C31 C36 1.375(6) . ? C31 C32 1.390(6) . ? C32 C33 1.384(6) . ? C33 C34 1.379(6) . ? C34 C35 1.395(6) . ? C35 C36 1.377(6) . ? C37 C42 1.391(6) . ? C37 C38 1.393(5) . ? C38 C39 1.365(6) . ? C39 C40 1.397(6) . ? C40 C41 1.410(6) . ? C41 C42 1.373(6) . ? 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 N1 C20 114.0(4) . . ? C5 N1 C21 113.5(4) . . ? C20 N1 C21 111.1(4) . . ? C11 N2 C23 116.6(4) . . ? C11 N2 C22 116.2(4) . . ? C23 N2 C22 110.1(4) . . ? C34 N3 C44 120.2(4) . . ? C34 N3 C43 121.4(4) . . ? C44 N3 C43 118.5(4) . . ? C40 N4 C45 120.9(5) . . ? C40 N4 C46 120.0(5) . . ? C45 N4 C46 118.9(4) . . ? O1 C1 C14 105.6(4) . . ? O1 C1 C8 109.1(3) . . ? C14 C1 C8 111.2(4) . . ? O1 C1 C2 108.9(4) . . ? C14 C1 C2 108.9(4) . . ? C8 C1 C2 112.9(4) . . ? C3 C2 C7 118.3(4) . . ? C3 C2 C1 123.4(4) . . ? C7 C2 C1 118.2(4) . . ? C2 C3 C4 121.3(5) . . ? C5 C4 C3 120.4(5) . . ? C4 C5 C6 119.1(4) . . ? C4 C5 N1 122.6(4) . . ? C6 C5 N1 118.4(4) . . ? C5 C6 C7 119.9(5) . . ? C2 C7 C6 121.0(5) . . ? C9 C8 C13 115.1(5) . . ? C9 C8 C1 124.1(4) . . ? C13 C8 C1 120.7(4) . . ? C8 C9 C10 122.8(5) . . ? C11 C10 C9 121.4(4) . . ? C10 C11 C12 116.7(4) . . ? C10 C11 N2 122.3(4) . . ? C12 C11 N2 121.0(4) . . ? C13 C12 C11 120.9(5) . . ? C12 C13 C8 123.1(5) . . ? C15 C14 C19 117.8(5) . . ? C15 C14 C1 122.6(5) . . ? C19 C14 C1 119.6(4) . . ? C14 C15 C16 120.6(5) . . ? C17 C16 C15 122.3(6) . . ? C16 C17 C18 117.3(6) . . ? C17 C18 C19 121.0(6) . . ? C14 C19 C18 121.0(5) . . ? O2 C24 C31 108.1(3) . . ? O2 C24 C37 110.4(4) . . ? C31 C24 C37 112.7(4) . . ? O2 C24 C25 104.2(4) . . ? C31 C24 C25 111.8(4) . . ? C37 C24 C25 109.3(4) . . ? C30 C25 C26 118.1(5) . . ? C30 C25 C24 121.1(4) . . ? C26 C25 C24 120.7(4) . . ? C27 C26 C25 120.7(5) . . ? C28 C27 C26 120.5(5) . . ? C27 C28 C29 119.7(6) . . ? C28 C29 C30 119.6(6) . . ? C29 C30 C25 121.4(5) . . ? C36 C31 C32 115.4(5) . . ? C36 C31 C24 124.9(4) . . ? C32 C31 C24 119.6(4) . . ? C33 C32 C31 122.8(5) . . ? C34 C33 C32 121.4(5) . . ? N3 C34 C33 121.5(5) . . ? N3 C34 C35 122.7(5) . . ? C33 C34 C35 115.9(5) . . ? C36 C35 C34 122.2(5) . . ? C31 C36 C35 122.3(5) . . ? C42 C37 C38 115.4(4) . . ? C42 C37 C24 122.2(4) . . ? C38 C37 C24 122.4(4) . . ? C39 C38 C37 122.8(5) . . ? C38 C39 C40 121.9(5) . . ? N4 C40 C39 122.7(5) . . ? N4 C40 C41 121.3(5) . . ? C39 C40 C41 115.9(5) . . ? C42 C41 C40 121.1(5) . . ? C41 C42 C37 122.9(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1O2 N2 0.76(4) 2.27(4) 3.022(6) 171(4) . O1 H1O1 N1 0.92(4) 2.10(4) 2.975(5) 157(4) 2_765 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.142 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.034 #===END data_alpha-CV _database_code_depnum_ccdc_archive 'CCDC 285203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H31 N3 O' _chemical_formula_weight 389.53 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.006(5) _cell_length_b 10.491(5) _cell_length_c 19.293(5) _cell_angle_alpha 86.37(2) _cell_angle_beta 88.40(2) _cell_angle_gamma 88.50(2) _cell_volume 2221.6(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'thin needles' _exptl_crystal_colour violet _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.556 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8433 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 69.99 _reflns_number_total 8433 _reflns_number_gt 6907 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0927P)^2^+0.2090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8433 _refine_ls_number_parameters 639 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.04267(17) 0.05540(16) 0.09755(9) 0.0794(5) Uani 1 1 d . . . N2 N 0.29249(15) 0.0735(2) 0.34284(10) 0.0920(6) Uani 1 1 d . . . N3 N 0.83879(16) 0.71530(14) 0.41433(10) 0.0774(5) Uani 1 1 d . . . N4 N 1.08901(15) -0.4328(2) 0.15684(10) 0.1019(7) Uani 1 1 d . . . N5 N 0.32682(18) -0.43469(16) 0.39348(8) 0.0805(5) Uani 1 1 d . . . N6 N 0.53499(12) 0.25243(11) 0.06148(7) 0.0540(3) Uani 1 1 d . . . O1 O 0.85528(11) 0.10899(10) 0.40919(6) 0.0574(3) Uani 1 1 d . . . O2 O 0.52660(10) -0.35784(9) 0.08411(5) 0.0488(2) Uani 1 1 d . . . C1 C 0.80014(13) 0.18724(13) 0.35247(7) 0.0459(3) Uani 1 1 d . . . C2 C 0.86919(12) 0.15667(13) 0.28564(8) 0.0471(3) Uani 1 1 d . . . C3 C 0.90124(15) 0.24837(15) 0.23418(9) 0.0561(4) Uani 1 1 d . . . C4 C 0.95859(17) 0.21661(17) 0.17261(9) 0.0616(4) Uani 1 1 d . . . C5 C 0.98616(14) 0.08914(16) 0.15965(8) 0.0560(4) Uani 1 1 d . . . C6 C 0.95194(15) -0.00387(15) 0.21089(9) 0.0560(4) Uani 1 1 d . . . C7 C 0.89472(14) 0.02930(14) 0.27181(9) 0.0527(3) Uani 1 1 d . . . C8 C 1.0881(2) 0.1545(3) 0.05005(12) 0.0948(7) Uani 1 1 d . . . H8A H 1.0221 0.2105 0.0354 0.142 Uiso 1 1 calc R . . H8B H 1.1255 0.1171 0.0103 0.142 Uiso 1 1 calc R . . H8C H 1.1471 0.2021 0.0726 0.142 Uiso 1 1 calc R . . C9 C 1.0985(2) -0.0694(2) 0.09464(13) 0.0923(7) Uani 1 1 d . . . H9A H 1.1548 -0.0832 0.1316 0.138 Uiso 1 1 calc R . . H9B H 1.1410 -0.0757 0.0508 0.138 Uiso 1 1 calc R . . H9C H 1.0369 -0.1328 0.0995 0.138 Uiso 1 1 calc R . . C10 C 0.66734(13) 0.14895(13) 0.34953(7) 0.0455(3) Uani 1 1 d . . . C11 C 0.60808(15) 0.14614(16) 0.28709(8) 0.0539(4) Uani 1 1 d . . . C12 C 0.48580(15) 0.12125(17) 0.28461(9) 0.0596(4) Uani 1 1 d . . . C13 C 0.41529(15) 0.09754(16) 0.34512(9) 0.0587(4) Uani 1 1 d . . . C14 C 0.47510(15) 0.09794(16) 0.40825(9) 0.0585(4) Uani 1 1 d . . . C15 C 0.59791(14) 0.12332(15) 0.40965(8) 0.0520(3) Uani 1 1 d . . . C16 C 0.21808(19) 0.0607(3) 0.40424(14) 0.1004(8) Uani 1 1 d . . . H16A H 0.2475 -0.0102 0.4335 0.151 Uiso 1 1 calc R . . H16B H 0.1358 0.0462 0.3920 0.151 Uiso 1 1 calc R . . H16C H 0.2206 0.1375 0.4286 0.151 Uiso 1 1 calc R . . C17 C 0.2329(2) 0.0875(4) 0.27709(17) 0.1510(16) Uani 1 1 d . . . H17A H 0.2367 0.1747 0.2590 0.227 Uiso 1 1 calc R . . H17B H 0.1494 0.0641 0.2835 0.227 Uiso 1 1 calc R . . H17C H 0.2729 0.0330 0.2450 0.227 Uiso 1 1 calc R . . C18 C 0.80931(13) 0.32817(13) 0.36827(7) 0.0456(3) Uani 1 1 d . . . C19 C 0.71120(14) 0.41321(14) 0.36487(8) 0.0502(3) Uani 1 1 d . . . C20 C 0.72070(15) 0.53987(15) 0.37965(9) 0.0542(4) Uani 1 1 d . . . C21 C 0.83029(15) 0.58848(14) 0.39925(8) 0.0535(4) Uani 1 1 d . . . C22 C 0.93036(16) 0.50324(16) 0.40223(9) 0.0594(4) Uani 1 1 d . . . C23 C 0.91951(15) 0.37695(15) 0.38646(9) 0.0552(4) Uani 1 1 d . . . C24 C 0.7328(2) 0.79831(16) 0.41105(11) 0.0741(5) Uani 1 1 d . . . H24A H 0.7030 0.8038 0.3646 0.111 Uiso 1 1 calc R . . H24B H 0.7537 0.8819 0.4237 0.111 Uiso 1 1 calc R . . H24C H 0.6710 0.7647 0.4427 0.111 Uiso 1 1 calc R . . C25 C 0.9535(2) 0.76600(19) 0.42905(13) 0.0904(7) Uani 1 1 d . . . H25A H 0.9863 0.7202 0.4692 0.136 Uiso 1 1 calc R . . H25B H 0.9432 0.8547 0.4378 0.136 Uiso 1 1 calc R . . H25C H 1.0084 0.7572 0.3900 0.136 Uiso 1 1 calc R . . C26 C 0.58291(12) -0.28882(12) 0.13704(7) 0.0400(3) Uani 1 1 d . . . C27 C 0.71566(12) -0.33538(12) 0.14308(7) 0.0409(3) Uani 1 1 d . . . C28 C 0.78360(14) -0.37204(14) 0.08589(8) 0.0499(3) Uani 1 1 d . . . C29 C 0.90568(15) -0.40572(16) 0.09014(9) 0.0581(4) Uani 1 1 d . . . C30 C 0.96629(14) -0.40253(16) 0.15262(9) 0.0597(4) Uani 1 1 d . . . C31 C 0.89724(15) -0.36867(18) 0.21037(9) 0.0619(4) Uani 1 1 d . . . C32 C 0.77526(14) -0.33566(16) 0.20527(8) 0.0527(3) Uani 1 1 d . . . C33 C 1.1639(2) -0.4447(3) 0.09721(16) 0.1089(9) Uani 1 1 d . . . H33A H 1.1432 -0.5201 0.0748 0.163 Uiso 1 1 calc R . . H33B H 1.2475 -0.4512 0.1103 0.163 Uiso 1 1 calc R . . H33C H 1.1522 -0.3711 0.0658 0.163 Uiso 1 1 calc R . . C34 C 1.1459(2) -0.4340(5) 0.22230(18) 0.182(2) Uani 1 1 d . . . H34A H 1.1483 -0.3484 0.2370 0.272 Uiso 1 1 calc R . . H34B H 1.2272 -0.4685 0.2180 0.272 Uiso 1 1 calc R . . H34C H 1.1004 -0.4860 0.2560 0.272 Uiso 1 1 calc R . . C35 C 0.51360(12) -0.32265(12) 0.20528(7) 0.0410(3) Uani 1 1 d . . . C36 C 0.47672(15) -0.23424(14) 0.25255(8) 0.0535(4) Uani 1 1 d . . . C37 C 0.41755(17) -0.27059(16) 0.31481(9) 0.0607(4) Uani 1 1 d . . . C38 C 0.39183(14) -0.39855(15) 0.33263(8) 0.0533(3) Uani 1 1 d . . . C39 C 0.43208(13) -0.48804(14) 0.28604(8) 0.0480(3) Uani 1 1 d . . . C40 C 0.49134(13) -0.45071(13) 0.22458(7) 0.0442(3) Uani 1 1 d . . . C41 C 0.3077(3) -0.3454(3) 0.44551(12) 0.1099(9) Uani 1 1 d . . . H41A H 0.3847 -0.3217 0.4623 0.165 Uiso 1 1 calc R . . H41B H 0.2598 -0.3836 0.4833 0.165 Uiso 1 1 calc R . . H41C H 0.2656 -0.2708 0.4261 0.165 Uiso 1 1 calc R . . C42 C 0.3116(3) -0.5670(2) 0.41297(13) 0.1035(8) Uani 1 1 d . . . H42A H 0.2812 -0.6090 0.3744 0.155 Uiso 1 1 calc R . . H42B H 0.2549 -0.5757 0.4516 0.155 Uiso 1 1 calc R . . H42C H 0.3885 -0.6052 0.4260 0.155 Uiso 1 1 calc R . . C43 C 0.57446(12) -0.14544(12) 0.11655(7) 0.0402(3) Uani 1 1 d . . . C44 C 0.46221(13) -0.08866(13) 0.10064(8) 0.0487(3) Uani 1 1 d . . . C45 C 0.44922(14) 0.04084(14) 0.08318(9) 0.0519(3) Uani 1 1 d . . . C46 C 0.54937(13) 0.12023(12) 0.08081(7) 0.0443(3) Uani 1 1 d . . . C47 C 0.66180(14) 0.06414(13) 0.09609(8) 0.0491(3) Uani 1 1 d . . . C48 C 0.67325(13) -0.06649(13) 0.11339(8) 0.0459(3) Uani 1 1 d . . . C49 C 0.42479(17) 0.31419(15) 0.08716(10) 0.0633(4) Uani 1 1 d . . . H49A H 0.3555 0.2779 0.0674 0.095 Uiso 1 1 calc R . . H49B H 0.4264 0.4040 0.0742 0.095 Uiso 1 1 calc R . . H49C H 0.4195 0.3015 0.1369 0.095 Uiso 1 1 calc R . . C50 C 0.64194(18) 0.32988(15) 0.06723(12) 0.0726(5) Uani 1 1 d . . . H50A H 0.6676 0.3242 0.1145 0.109 Uiso 1 1 calc R . . H50B H 0.6222 0.4173 0.0533 0.109 Uiso 1 1 calc R . . H50C H 0.7064 0.2992 0.0376 0.109 Uiso 1 1 calc R . . H2O H 0.515(2) -0.305(2) 0.0455(12) 0.089(7) Uiso 1 1 d . . . H19 H 0.6337(15) 0.3839(15) 0.3523(8) 0.051(4) Uiso 1 1 d . . . H20 H 0.6532(18) 0.5962(19) 0.3751(10) 0.071(5) Uiso 1 1 d . . . H23 H 0.9906(17) 0.3204(18) 0.3866(10) 0.068(5) Uiso 1 1 d . . . H32 H 0.7348(16) -0.3097(17) 0.2452(9) 0.058(5) Uiso 1 1 d . . . H36 H 0.4933(16) -0.1481(19) 0.2424(9) 0.065(5) Uiso 1 1 d . . . H44 H 0.3883(16) -0.1403(17) 0.1027(9) 0.058(4) Uiso 1 1 d . . . H45 H 0.3705(16) 0.0757(17) 0.0732(9) 0.061(5) Uiso 1 1 d . . . H47 H 0.7339(17) 0.1131(17) 0.0957(9) 0.060(5) Uiso 1 1 d . . . H48 H 0.7514(15) -0.0979(15) 0.1237(8) 0.046(4) Uiso 1 1 d . . . H11 H 0.6511(16) 0.1594(16) 0.2437(9) 0.058(5) Uiso 1 1 d . . . H39 H 0.4168(15) -0.5779(18) 0.2967(9) 0.060(5) Uiso 1 1 d . . . H15 H 0.6358(16) 0.1243(16) 0.4558(9) 0.059(5) Uiso 1 1 d . . . H40 H 0.5187(15) -0.5145(17) 0.1938(9) 0.055(4) Uiso 1 1 d . . . H12 H 0.4467(18) 0.1218(19) 0.2400(11) 0.072(5) Uiso 1 1 d . . . H3 H 0.8818(16) 0.3387(19) 0.2420(9) 0.067(5) Uiso 1 1 d . . . H7 H 0.8713(16) -0.0355(18) 0.3063(9) 0.064(5) Uiso 1 1 d . . . H22 H 1.0127(17) 0.5297(17) 0.4137(9) 0.064(5) Uiso 1 1 d . . . H28 H 0.7402(16) -0.3756(17) 0.0405(9) 0.061(5) Uiso 1 1 d . . . H14 H 0.4312(18) 0.0826(19) 0.4521(11) 0.072(5) Uiso 1 1 d . . . H4 H 0.9802(18) 0.285(2) 0.1382(11) 0.078(6) Uiso 1 1 d . . . H29 H 0.9505(18) -0.4262(19) 0.0464(11) 0.077(6) Uiso 1 1 d . . . H6 H 0.9653(16) -0.0929(18) 0.2019(9) 0.064(5) Uiso 1 1 d . . . H31 H 0.9364(19) -0.363(2) 0.2537(12) 0.081(6) Uiso 1 1 d . . . H37 H 0.3923(18) -0.203(2) 0.3451(10) 0.078(6) Uiso 1 1 d . . . H1O H 0.882(4) 0.149(4) 0.439(2) 0.203(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0936(12) 0.0728(10) 0.0714(10) -0.0118(8) 0.0232(9) -0.0015(9) N2 0.0535(9) 0.1350(17) 0.0901(12) -0.0202(11) -0.0035(8) -0.0191(10) N3 0.0832(11) 0.0455(8) 0.1056(13) -0.0160(8) -0.0079(9) -0.0077(7) N4 0.0490(9) 0.160(2) 0.0931(13) 0.0066(13) -0.0013(8) 0.0267(10) N5 0.1100(13) 0.0711(10) 0.0578(8) 0.0042(7) 0.0286(8) -0.0044(9) N6 0.0681(8) 0.0323(6) 0.0614(7) -0.0008(5) -0.0024(6) 0.0011(5) O1 0.0669(7) 0.0457(6) 0.0591(6) 0.0048(5) -0.0146(5) 0.0014(5) O2 0.0638(6) 0.0369(5) 0.0463(5) -0.0022(4) -0.0096(4) -0.0033(4) C1 0.0498(7) 0.0390(7) 0.0487(7) 0.0001(5) -0.0069(6) 0.0004(5) C2 0.0435(7) 0.0413(7) 0.0563(8) -0.0021(6) -0.0017(6) -0.0015(5) C3 0.0653(9) 0.0408(8) 0.0615(9) -0.0008(6) 0.0019(7) 0.0000(7) C4 0.0706(10) 0.0516(9) 0.0617(9) 0.0026(7) 0.0066(8) -0.0062(7) C5 0.0515(8) 0.0585(9) 0.0587(9) -0.0089(7) 0.0020(7) -0.0034(7) C6 0.0566(9) 0.0445(8) 0.0675(10) -0.0086(7) 0.0005(7) -0.0011(6) C7 0.0543(8) 0.0408(7) 0.0626(9) -0.0003(6) 0.0031(7) -0.0026(6) C8 0.1038(17) 0.1044(17) 0.0749(13) -0.0054(12) 0.0303(12) -0.0141(13) C9 0.0962(15) 0.0891(15) 0.0925(15) -0.0299(12) 0.0241(12) 0.0097(12) C10 0.0502(7) 0.0367(6) 0.0499(7) -0.0042(5) -0.0035(6) -0.0011(5) C11 0.0570(9) 0.0589(9) 0.0460(8) -0.0055(6) -0.0013(7) -0.0039(7) C12 0.0569(9) 0.0697(10) 0.0539(9) -0.0115(7) -0.0096(7) -0.0031(7) C13 0.0514(8) 0.0569(9) 0.0690(10) -0.0106(7) -0.0041(7) -0.0047(7) C14 0.0577(9) 0.0605(9) 0.0573(9) -0.0043(7) 0.0054(7) -0.0084(7) C15 0.0564(8) 0.0517(8) 0.0485(8) -0.0035(6) -0.0045(6) -0.0034(6) C16 0.0569(11) 0.127(2) 0.1166(19) -0.0011(16) 0.0114(12) -0.0180(12) C17 0.0606(14) 0.281(5) 0.117(2) -0.029(3) -0.0268(14) -0.025(2) C18 0.0495(7) 0.0416(7) 0.0456(7) -0.0021(5) -0.0044(6) -0.0013(6) C19 0.0512(8) 0.0425(7) 0.0568(8) -0.0008(6) -0.0060(6) -0.0015(6) C20 0.0581(9) 0.0419(7) 0.0620(9) -0.0005(6) -0.0036(7) 0.0031(6) C21 0.0662(9) 0.0405(7) 0.0542(8) -0.0034(6) -0.0019(7) -0.0048(6) C22 0.0580(9) 0.0526(9) 0.0688(10) -0.0064(7) -0.0112(8) -0.0100(7) C23 0.0510(8) 0.0483(8) 0.0668(9) -0.0052(7) -0.0087(7) 0.0001(6) C24 0.1011(14) 0.0408(8) 0.0802(12) -0.0078(8) 0.0066(10) 0.0001(9) C25 0.1097(17) 0.0542(11) 0.1103(17) -0.0094(10) -0.0313(14) -0.0193(11) C26 0.0453(7) 0.0329(6) 0.0417(6) -0.0028(5) -0.0019(5) -0.0002(5) C27 0.0465(7) 0.0313(6) 0.0442(7) 0.0015(5) 0.0011(5) 0.0015(5) C28 0.0526(8) 0.0495(8) 0.0471(8) -0.0033(6) 0.0017(6) 0.0040(6) C29 0.0534(8) 0.0604(9) 0.0590(9) -0.0030(7) 0.0093(7) 0.0100(7) C30 0.0469(8) 0.0615(9) 0.0685(10) 0.0088(8) 0.0010(7) 0.0081(7) C31 0.0533(9) 0.0786(11) 0.0524(9) 0.0065(8) -0.0078(7) 0.0039(8) C32 0.0510(8) 0.0624(9) 0.0440(7) -0.0006(6) 0.0005(6) 0.0045(7) C33 0.0572(12) 0.135(2) 0.133(2) -0.0169(17) 0.0184(13) 0.0235(13) C34 0.0588(14) 0.361(7) 0.120(2) 0.004(3) -0.0261(15) 0.050(2) C35 0.0413(6) 0.0360(6) 0.0454(7) -0.0016(5) -0.0009(5) 0.0015(5) C36 0.0687(10) 0.0374(7) 0.0539(8) -0.0046(6) 0.0090(7) -0.0004(6) C37 0.0786(11) 0.0492(8) 0.0538(9) -0.0088(7) 0.0138(8) 0.0024(7) C38 0.0565(8) 0.0548(8) 0.0473(8) 0.0031(6) 0.0047(6) 0.0001(7) C39 0.0495(7) 0.0411(7) 0.0526(8) 0.0032(6) -0.0015(6) -0.0026(6) C40 0.0474(7) 0.0370(7) 0.0482(7) -0.0034(5) -0.0009(6) 0.0002(5) C41 0.155(2) 0.1027(18) 0.0692(13) -0.0071(12) 0.0474(15) 0.0001(17) C42 0.142(2) 0.0813(15) 0.0816(14) 0.0212(12) 0.0447(14) -0.0083(14) C43 0.0460(7) 0.0345(6) 0.0400(6) -0.0010(5) -0.0008(5) 0.0007(5) C44 0.0431(7) 0.0372(7) 0.0653(9) 0.0012(6) -0.0035(6) -0.0019(5) C45 0.0476(8) 0.0388(7) 0.0687(9) 0.0013(6) -0.0076(7) 0.0044(6) C46 0.0562(8) 0.0331(6) 0.0432(7) -0.0010(5) -0.0012(6) 0.0006(5) C47 0.0492(8) 0.0388(7) 0.0592(8) -0.0001(6) -0.0029(6) -0.0064(6) C48 0.0437(7) 0.0384(7) 0.0557(8) -0.0019(6) -0.0051(6) 0.0013(5) C49 0.0745(11) 0.0402(8) 0.0748(11) -0.0042(7) -0.0068(8) 0.0105(7) C50 0.0802(12) 0.0357(8) 0.1013(14) 0.0035(8) -0.0026(10) -0.0075(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 N1 C5 1.396(2) . ? N1 C8 1.432(3) . ? N1 C9 1.435(3) . ? N2 C13 1.384(2) . ? N2 C16 1.423(3) . ? N2 C17 1.442(3) . ? N3 C21 1.386(2) . ? N3 C25 1.426(3) . ? N3 C24 1.438(3) . ? N4 C30 1.383(2) . ? N4 C33 1.407(3) . ? N4 C34 1.424(4) . ? N5 C38 1.395(2) . ? N5 C41 1.423(3) . ? N5 C42 1.428(3) . ? N6 C46 1.4192(18) . ? N6 C49 1.450(2) . ? N6 C50 1.458(2) . ? O1 C1 1.4618(17) . ? O2 C26 1.4504(16) . ? C1 C2 1.526(2) . ? C1 C10 1.529(2) . ? C1 C18 1.535(2) . ? C2 C3 1.383(2) . ? C2 C7 1.399(2) . ? C3 C4 1.385(2) . ? C4 C5 1.400(2) . ? C5 C6 1.396(2) . ? C6 C7 1.378(2) . ? C10 C15 1.387(2) . ? C10 C11 1.388(2) . ? C11 C12 1.380(2) . ? C12 C13 1.396(2) . ? C13 C14 1.401(2) . ? C14 C15 1.386(2) . ? C18 C19 1.383(2) . ? C18 C23 1.391(2) . ? C19 C20 1.384(2) . ? C20 C21 1.393(2) . ? C21 C22 1.401(2) . ? C22 C23 1.387(2) . ? C26 C35 1.5297(18) . ? C26 C43 1.5320(18) . ? C26 C27 1.5336(19) . ? C27 C32 1.383(2) . ? C27 C28 1.385(2) . ? C28 C29 1.384(2) . ? C29 C30 1.397(2) . ? C30 C31 1.391(2) . ? C31 C32 1.382(2) . ? C35 C36 1.387(2) . ? C35 C40 1.3973(19) . ? C36 C37 1.387(2) . ? C37 C38 1.399(2) . ? C38 C39 1.396(2) . ? C39 C40 1.377(2) . ? C43 C48 1.382(2) . ? C43 C44 1.391(2) . ? C44 C45 1.384(2) . ? C45 C46 1.397(2) . ? C46 C47 1.387(2) . ? C47 C48 1.393(2) . ? 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 N1 C8 118.78(17) . . ? C5 N1 C9 118.78(17) . . ? C8 N1 C9 117.43(18) . . ? C13 N2 C16 121.78(18) . . ? C13 N2 C17 119.2(2) . . ? C16 N2 C17 117.81(19) . . ? C21 N3 C25 120.35(17) . . ? C21 N3 C24 119.92(16) . . ? C25 N3 C24 119.63(16) . . ? C30 N4 C33 121.95(19) . . ? C30 N4 C34 119.5(2) . . ? C33 N4 C34 117.9(2) . . ? C38 N5 C41 119.48(18) . . ? C38 N5 C42 119.81(17) . . ? C41 N5 C42 118.09(18) . . ? C46 N6 C49 115.87(13) . . ? C46 N6 C50 116.28(13) . . ? C49 N6 C50 112.51(14) . . ? O1 C1 C2 107.26(12) . . ? O1 C1 C10 107.30(11) . . ? C2 C1 C10 110.55(12) . . ? O1 C1 C18 108.26(11) . . ? C2 C1 C18 112.23(12) . . ? C10 C1 C18 111.02(11) . . ? C3 C2 C7 116.70(14) . . ? C3 C2 C1 123.47(13) . . ? C7 C2 C1 119.66(13) . . ? C2 C3 C4 121.95(15) . . ? C3 C4 C5 121.08(16) . . ? C6 C5 N1 121.03(16) . . ? C6 C5 C4 117.15(15) . . ? N1 C5 C4 121.80(16) . . ? C7 C6 C5 121.04(15) . . ? C6 C7 C2 122.04(15) . . ? C15 C10 C11 116.63(14) . . ? C15 C10 C1 121.32(13) . . ? C11 C10 C1 121.92(13) . . ? C12 C11 C10 121.98(15) . . ? C11 C12 C13 121.47(15) . . ? N2 C13 C12 121.62(16) . . ? N2 C13 C14 121.58(17) . . ? C12 C13 C14 116.79(15) . . ? C15 C14 C13 120.85(16) . . ? C14 C15 C10 122.26(15) . . ? C19 C18 C23 116.46(14) . . ? C19 C18 C1 122.88(13) . . ? C23 C18 C1 120.65(13) . . ? C20 C19 C18 122.23(15) . . ? C19 C20 C21 121.49(15) . . ? N3 C21 C20 121.09(15) . . ? N3 C21 C22 122.28(15) . . ? C20 C21 C22 116.63(14) . . ? C23 C22 C21 121.10(15) . . ? C22 C23 C18 122.06(15) . . ? O2 C26 C35 106.58(10) . . ? O2 C26 C43 108.91(10) . . ? C35 C26 C43 111.88(10) . . ? O2 C26 C27 108.56(10) . . ? C35 C26 C27 109.51(10) . . ? C43 C26 C27 111.24(11) . . ? C32 C27 C28 116.79(13) . . ? C32 C27 C26 121.40(12) . . ? C28 C27 C26 121.71(12) . . ? C29 C28 C27 121.91(14) . . ? C28 C29 C30 121.10(15) . . ? N4 C30 C31 121.68(17) . . ? N4 C30 C29 121.44(17) . . ? C31 C30 C29 116.89(14) . . ? C32 C31 C30 121.24(15) . . ? C31 C32 C27 122.03(15) . . ? C36 C35 C40 116.51(13) . . ? C36 C35 C26 124.08(12) . . ? C40 C35 C26 119.29(12) . . ? C35 C36 C37 121.76(14) . . ? C36 C37 C38 121.34(14) . . ? N5 C38 C39 121.56(15) . . ? N5 C38 C37 121.49(15) . . ? C39 C38 C37 116.94(14) . . ? C40 C39 C38 121.10(14) . . ? C39 C40 C35 122.29(13) . . ? C48 C43 C44 116.81(12) . . ? C48 C43 C26 123.60(12) . . ? C44 C43 C26 119.59(12) . . ? C45 C44 C43 121.89(13) . . ? C44 C45 C46 120.94(13) . . ? C47 C46 C45 117.51(13) . . ? C47 C46 N6 122.19(13) . . ? C45 C46 N6 120.28(13) . . ? C46 C47 C48 120.77(13) . . ? C43 C48 C47 122.07(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O N6 0.91(2) 2.18(2) 3.0408(18) 156(2) 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 69.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.221 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.042 #===END data_beta-CV _database_code_depnum_ccdc_archive 'CCDC 285204' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H31 N3 O' _chemical_formula_weight 389.53 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.860(10) _cell_length_b 10.470(10) _cell_length_c 19.95(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.24(9) _cell_angle_gamma 90.00 _cell_volume 2239(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour 'pale violet' _exptl_crystal_size_max .16 _exptl_crystal_size_mid .08 _exptl_crystal_size_min .04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.552 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7632 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 70.10 _reflns_number_total 3963 _reflns_number_gt 2171 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1625P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3963 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1326 _refine_ls_R_factor_gt 0.0964 _refine_ls_wR_factor_ref 0.2601 _refine_ls_wR_factor_gt 0.2197 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.001 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 0.3846(2) 0.6105(2) 0.09092(11) 0.0582(6) Uani 1 1 d . . . H1 H 0.3592 0.6441 0.0542 0.087 Uiso 1 1 calc R . . N1 N -0.1726(3) 0.5526(5) 0.1512(2) 0.1048(14) Uani 1 1 d . . . N2 N 0.3617(3) 1.2181(3) 0.08331(18) 0.0775(10) Uani 1 1 d . . . N3 N 0.6489(4) 0.5456(3) 0.39592(16) 0.0837(11) Uani 1 1 d . . . C1 C 0.3394(3) 0.6826(3) 0.14498(15) 0.0473(7) Uani 1 1 d . . . C2 C 0.3435(3) 0.8242(3) 0.12809(15) 0.0474(7) Uani 1 1 d . . . C3 C 0.4502(4) 0.8784(3) 0.10987(19) 0.0602(9) Uani 1 1 d . . . C4 C 0.4570(4) 1.0077(3) 0.09459(19) 0.0628(10) Uani 1 1 d . . . C5 C 0.3564(3) 1.0883(3) 0.09851(17) 0.0569(8) Uani 1 1 d . . . C6 C 0.2511(4) 1.0357(3) 0.11804(17) 0.0562(9) Uani 1 1 d . . . C7 C 0.2447(3) 0.9056(3) 0.13218(16) 0.0517(8) Uani 1 1 d . . . C8 C 0.2053(3) 0.6392(3) 0.14660(15) 0.0477(7) Uani 1 1 d . . . C9 C 0.1584(3) 0.6321(3) 0.20717(17) 0.0576(9) Uani 1 1 d . . . C10 C 0.0354(4) 0.6043(4) 0.2092(2) 0.0669(10) Uani 1 1 d . . . C11 C -0.0484(3) 0.5814(4) 0.1500(2) 0.0654(10) Uani 1 1 d . . . C12 C -0.0015(4) 0.5871(3) 0.0883(2) 0.0631(9) Uani 1 1 d . . . C13 C 0.1232(3) 0.6154(3) 0.08795(17) 0.0550(8) Uani 1 1 d . . . C14 C 0.4242(3) 0.6496(3) 0.21086(15) 0.0484(7) Uani 1 1 d . . . C15 C 0.4703(4) 0.7398(3) 0.25909(18) 0.0605(9) Uani 1 1 d . . . C16 C 0.5432(4) 0.7063(4) 0.31992(19) 0.0660(10) Uani 1 1 d . . . C17 C 0.5739(3) 0.5789(3) 0.33605(17) 0.0576(9) Uani 1 1 d . . . C18 C 0.5236(3) 0.4872(3) 0.28828(17) 0.0557(8) Uani 1 1 d . . . C19 C 0.4516(3) 0.5220(3) 0.22773(17) 0.0526(8) Uani 1 1 d . . . C20 C 0.4741(4) 1.2745(4) 0.0708(3) 0.0956(14) Uani 1 1 d . . . H20A H 0.4607 1.3638 0.0616 0.143 Uiso 1 1 calc R . . H20B H 0.5005 1.2339 0.0324 0.143 Uiso 1 1 calc R . . H20C H 0.5372 1.2640 0.1100 0.143 Uiso 1 1 calc R . . C21 C 0.2566(4) 1.2980(4) 0.0898(2) 0.0826(12) Uani 1 1 d . . . H21A H 0.2742 1.3843 0.0780 0.124 Uiso 1 1 calc R . . H21B H 0.2411 1.2955 0.1358 0.124 Uiso 1 1 calc R . . H21C H 0.1843 1.2677 0.0599 0.124 Uiso 1 1 calc R . . C22 C 0.6801(5) 0.6371(5) 0.4486(2) 0.1104(18) Uani 1 1 d . . . H22A H 0.7325 0.5980 0.4864 0.166 Uiso 1 1 calc R . . H22B H 0.6052 0.6678 0.4629 0.166 Uiso 1 1 calc R . . H22C H 0.7236 0.7073 0.4321 0.166 Uiso 1 1 calc R . . C23 C 0.6680(5) 0.4131(5) 0.4137(3) 0.1118(19) Uani 1 1 d . . . H23A H 0.7218 0.4065 0.4567 0.168 Uiso 1 1 calc R . . H23B H 0.7057 0.3706 0.3795 0.168 Uiso 1 1 calc R . . H23C H 0.5892 0.3739 0.4167 0.168 Uiso 1 1 calc R . . C24 C -0.2609(4) 0.5455(6) 0.0911(3) 0.1119(18) Uani 1 1 d . . . H24A H -0.3416 0.5267 0.1024 0.168 Uiso 1 1 calc R . . H24B H -0.2372 0.4792 0.0625 0.168 Uiso 1 1 calc R . . H24C H -0.2639 0.6258 0.0676 0.168 Uiso 1 1 calc R . . C25 C -0.2182(5) 0.5586(9) 0.2147(3) 0.176(4) Uani 1 1 d . . . H25A H -0.3055 0.5383 0.2077 0.264 Uiso 1 1 calc R . . H25B H -0.2059 0.6432 0.2332 0.264 Uiso 1 1 calc R . . H25C H -0.1736 0.4983 0.2459 0.264 Uiso 1 1 calc R . . H6 H 0.172(3) 1.087(4) 0.1211(17) 0.071(11) Uiso 1 1 d . . . H9 H 0.215(4) 0.649(4) 0.251(2) 0.088(13) Uiso 1 1 d . . . H12 H -0.065(3) 0.568(4) 0.044(2) 0.079(11) Uiso 1 1 d . . . H4 H 0.532(4) 1.039(4) 0.082(2) 0.094(14) Uiso 1 1 d . . . H13 H 0.148(3) 0.616(3) 0.0426(17) 0.064(10) Uiso 1 1 d . . . H10 H -0.001(4) 0.602(4) 0.250(2) 0.095(14) Uiso 1 1 d . . . H3 H 0.523(4) 0.818(4) 0.1087(18) 0.081(12) Uiso 1 1 d . . . H7 H 0.166(3) 0.878(3) 0.1452(15) 0.052(9) Uiso 1 1 d . . . H16 H 0.581(3) 0.770(4) 0.3554(18) 0.073(11) Uiso 1 1 d . . . H19 H 0.417(3) 0.449(3) 0.1926(16) 0.060(9) Uiso 1 1 d . . . H18 H 0.547(4) 0.396(4) 0.299(2) 0.096(14) Uiso 1 1 d . . . H15 H 0.453(4) 0.841(5) 0.250(2) 0.111(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0748(17) 0.0459(12) 0.0577(13) -0.0037(10) 0.0219(11) 0.0037(11) N1 0.055(2) 0.153(4) 0.107(3) 0.025(3) 0.018(2) -0.020(2) N2 0.086(2) 0.0351(15) 0.115(3) 0.0115(16) 0.026(2) -0.0065(15) N3 0.116(3) 0.064(2) 0.0623(19) 0.0076(15) -0.0129(18) 0.005(2) C1 0.0563(19) 0.0363(15) 0.0509(16) 0.0011(12) 0.0135(13) -0.0003(13) C2 0.0537(19) 0.0385(16) 0.0515(16) 0.0028(12) 0.0132(13) -0.0019(13) C3 0.062(2) 0.0443(18) 0.077(2) 0.0047(16) 0.0178(17) -0.0002(16) C4 0.066(3) 0.0449(18) 0.082(2) 0.0106(16) 0.0250(19) -0.0075(17) C5 0.071(2) 0.0401(17) 0.0601(18) 0.0012(14) 0.0106(16) -0.0042(15) C6 0.064(2) 0.0377(16) 0.068(2) 0.0035(14) 0.0130(16) 0.0028(15) C7 0.054(2) 0.0423(17) 0.0606(18) 0.0018(14) 0.0149(15) -0.0007(14) C8 0.0505(19) 0.0410(16) 0.0519(16) 0.0029(12) 0.0093(13) -0.0014(13) C9 0.058(2) 0.062(2) 0.0548(18) 0.0082(15) 0.0149(16) -0.0025(16) C10 0.063(3) 0.075(3) 0.066(2) 0.0135(18) 0.0189(18) 0.0003(19) C11 0.050(2) 0.061(2) 0.086(3) 0.0128(18) 0.0149(18) -0.0037(16) C12 0.061(2) 0.058(2) 0.070(2) -0.0011(17) 0.0090(18) -0.0046(17) C13 0.058(2) 0.0514(19) 0.0565(19) -0.0022(14) 0.0125(15) -0.0046(15) C14 0.0528(18) 0.0383(15) 0.0547(17) 0.0011(12) 0.0103(13) -0.0013(13) C15 0.076(2) 0.0431(18) 0.060(2) -0.0031(15) 0.0046(17) -0.0026(16) C16 0.086(3) 0.0471(19) 0.061(2) -0.0006(16) 0.0004(18) -0.0018(18) C17 0.065(2) 0.0515(18) 0.0551(18) 0.0066(14) 0.0048(15) 0.0020(16) C18 0.060(2) 0.0453(18) 0.0620(19) 0.0023(15) 0.0096(15) 0.0000(15) C19 0.056(2) 0.0387(16) 0.0627(19) 0.0031(13) 0.0091(15) 0.0008(14) C20 0.116(4) 0.054(2) 0.125(4) 0.003(2) 0.044(3) -0.022(2) C21 0.108(3) 0.0426(19) 0.096(3) 0.0023(19) 0.014(2) 0.004(2) C22 0.151(5) 0.098(4) 0.070(3) -0.005(2) -0.021(3) -0.003(3) C23 0.151(5) 0.072(3) 0.098(3) 0.031(3) -0.025(3) 0.011(3) C24 0.060(3) 0.127(5) 0.146(5) -0.004(4) 0.005(3) -0.020(3) C25 0.073(4) 0.334(11) 0.133(5) 0.045(6) 0.050(4) -0.025(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 C1 1.464(4) . ? N1 C11 1.386(5) . ? N1 C24 1.411(6) . ? N1 C25 1.435(7) . ? N2 C5 1.396(4) . ? N2 C20 1.413(5) . ? N2 C21 1.438(5) . ? N3 C17 1.378(4) . ? N3 C22 1.422(5) . ? N3 C23 1.438(5) . ? C1 C14 1.519(4) . ? C1 C8 1.530(5) . ? C1 C2 1.523(4) . ? C2 C7 1.383(4) . ? C2 C3 1.390(5) . ? C3 C4 1.392(5) . ? C4 C5 1.393(5) . ? C5 C6 1.380(5) . ? C6 C7 1.396(4) . ? C8 C13 1.376(5) . ? C8 C9 1.387(4) . ? C9 C10 1.374(5) . ? C10 C11 1.391(5) . ? C11 C12 1.407(5) . ? C12 C13 1.387(5) . ? C14 C15 1.384(4) . ? C14 C19 1.398(4) . ? C15 C16 1.384(5) . ? C16 C17 1.400(5) . ? C17 C18 1.400(5) . ? C18 C19 1.378(5) . ? 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 C11 N1 C24 121.8(4) . . ? C11 N1 C25 118.7(4) . . ? C24 N1 C25 118.0(4) . . ? C5 N2 C20 120.8(4) . . ? C5 N2 C21 119.1(3) . . ? C20 N2 C21 119.5(3) . . ? C17 N3 C22 120.5(4) . . ? C17 N3 C23 119.9(3) . . ? C22 N3 C23 117.4(4) . . ? O1 C1 C14 106.9(2) . . ? O1 C1 C8 107.2(2) . . ? C14 C1 C8 111.2(2) . . ? O1 C1 C2 108.3(2) . . ? C14 C1 C2 112.2(2) . . ? C8 C1 C2 110.8(3) . . ? C7 C2 C3 116.9(3) . . ? C7 C2 C1 122.4(3) . . ? C3 C2 C1 120.7(3) . . ? C2 C3 C4 122.0(4) . . ? C3 C4 C5 120.5(3) . . ? C6 C5 C4 117.9(3) . . ? C6 C5 N2 121.0(3) . . ? C4 C5 N2 121.2(3) . . ? C5 C6 C7 121.1(3) . . ? C2 C7 C6 121.7(3) . . ? C13 C8 C9 116.9(3) . . ? C13 C8 C1 121.7(3) . . ? C9 C8 C1 121.2(3) . . ? C10 C9 C8 122.1(3) . . ? C9 C10 C11 121.3(4) . . ? N1 C11 C10 122.0(4) . . ? N1 C11 C12 120.9(4) . . ? C10 C11 C12 117.1(4) . . ? C13 C12 C11 120.3(4) . . ? C8 C13 C12 122.3(3) . . ? C15 C14 C19 116.5(3) . . ? C15 C14 C1 123.2(3) . . ? C19 C14 C1 120.2(3) . . ? C16 C15 C14 121.9(3) . . ? C15 C16 C17 121.7(3) . . ? N3 C17 C18 121.9(3) . . ? N3 C17 C16 121.7(3) . . ? C18 C17 C16 116.4(3) . . ? C19 C18 C17 121.3(3) . . ? C18 C19 C14 122.2(3) . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 70.10 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.634 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.149 #===END data_alpha-PG _database_code_depnum_ccdc_archive 'CCDC 285205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N3 O' _chemical_formula_weight 347.45 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.67(7) _cell_length_b 7.760(10) _cell_length_c 24.24(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.6(2) _cell_angle_gamma 90.00 _cell_volume 1997(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour white _exptl_crystal_size_max .14 _exptl_crystal_size_mid .11 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5643 _diffrn_reflns_av_R_equivalents 0.2513 _diffrn_reflns_av_sigmaI/netI 0.4044 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 60.05 _reflns_number_total 2964 _reflns_number_gt 478 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0013P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2964 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3189 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 0.656 _refine_ls_restrained_S_all 0.656 _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 0.7604(6) 0.1823(7) 0.1653(2) 0.0612(19) Uani 1 1 d . . . N2 N 1.3639(7) 0.1369(12) 0.2004(4) 0.108(3) Uani 1 1 d . . . N3 N 0.6900(8) 0.3856(10) -0.0867(3) 0.091(3) Uani 1 1 d . . . C1 C 0.8353(8) 0.0932(10) 0.1280(4) 0.056(3) Uani 1 1 d . . . C2 C 0.7962(5) -0.0999(5) 0.1316(3) 0.056(3) Uani 1 1 d G . . C3 C 0.7685(4) -0.1632(7) 0.18272(19) 0.063(3) Uani 1 1 d G . . H3 H 0.7641 -0.0883 0.2124 0.076 Uiso 1 1 calc R . . C4 C 0.7475(4) -0.3384(8) 0.18939(17) 0.077(3) Uani 1 1 d G . . H4 H 0.7290 -0.3808 0.2236 0.093 Uiso 1 1 calc R . . N1 N 0.7541(4) -0.4503(5) 0.1450(3) 0.067(2) Uani 1 1 d G . . C5 C 0.7818(4) -0.3870(7) 0.09392(19) 0.098(4) Uani 1 1 d G . . H5 H 0.7862 -0.4619 0.0642 0.118 Uiso 1 1 calc R . . C6 C 0.8028(4) -0.2118(8) 0.08725(17) 0.077(3) Uani 1 1 d G . . H6 H 0.8213 -0.1694 0.0531 0.093 Uiso 1 1 calc R . . C7 C 0.9803(4) 0.1066(8) 0.1489(3) 0.056(3) Uani 1 1 d G . . C8 C 1.0663(7) 0.0144(6) 0.12101(16) 0.070(3) Uani 1 1 d G . . H8 H 1.0384 -0.0531 0.0906 0.084 Uiso 1 1 calc R . . C9 C 1.1940(6) 0.0230(6) 0.1387(2) 0.075(3) Uani 1 1 d G . . H9 H 1.2516 -0.0387 0.1200 0.090 Uiso 1 1 calc R . . C10 C 1.2358(4) 0.1238(8) 0.1842(3) 0.062(3) Uani 1 1 d G . . C11 C 1.1498(7) 0.2160(6) 0.21205(17) 0.070(3) Uani 1 1 d G . . H11 H 1.1777 0.2835 0.2425 0.084 Uiso 1 1 calc R . . C12 C 1.0220(6) 0.2075(6) 0.1944(2) 0.060(3) Uani 1 1 d G . . H12 H 0.9645 0.2692 0.2131 0.072 Uiso 1 1 calc R . . C13 C 1.4548(7) 0.0474(11) 0.1708(3) 0.114(4) Uani 1 1 d . . . H13A H 1.4533 -0.0732 0.1795 0.171 Uiso 1 1 calc R . . H13B H 1.5373 0.0928 0.1815 0.171 Uiso 1 1 calc R . . H13C H 1.4345 0.0630 0.1316 0.171 Uiso 1 1 calc R . . C14 C 1.4119(7) 0.2352(11) 0.2467(4) 0.117(4) Uani 1 1 d . . . H14A H 1.3984 0.3554 0.2390 0.175 Uiso 1 1 calc R . . H14B H 1.5005 0.2136 0.2544 0.175 Uiso 1 1 calc R . . H14C H 1.3695 0.2032 0.2784 0.175 Uiso 1 1 calc R . . C15 C 0.8012(7) 0.1667(6) 0.06832(17) 0.057(3) Uani 1 1 d G . . C16 C 0.8904(4) 0.2389(7) 0.0372(3) 0.065(3) Uani 1 1 d G . . H16 H 0.9749 0.2395 0.0509 0.078 Uiso 1 1 calc R . . C17 C 0.8534(6) 0.3102(6) -0.0145(3) 0.070(3) Uani 1 1 d G . . H17 H 0.9131 0.3585 -0.0353 0.084 Uiso 1 1 calc R . . C18 C 0.7271(8) 0.3092(6) -0.03495(18) 0.070(3) Uani 1 1 d G . . C19 C 0.6378(4) 0.2370(8) -0.0038(3) 0.088(3) Uani 1 1 d G . . H19 H 0.5533 0.2363 -0.0175 0.106 Uiso 1 1 calc R . . C20 C 0.6749(6) 0.1657(6) 0.0478(3) 0.075(3) Uani 1 1 d G . . H20 H 0.6151 0.1174 0.0687 0.090 Uiso 1 1 calc R . . C21 C 0.7798(8) 0.4761(11) -0.1156(3) 0.127(4) Uani 1 1 d . . . H21A H 0.8050 0.5794 -0.0958 0.191 Uiso 1 1 calc R . . H21B H 0.7428 0.5054 -0.1521 0.191 Uiso 1 1 calc R . . H21C H 0.8522 0.4042 -0.1185 0.191 Uiso 1 1 calc R . . C22 C 0.5605(8) 0.4266(12) -0.1018(4) 0.147(5) Uani 1 1 d . . . H22A H 0.5084 0.3364 -0.0894 0.220 Uiso 1 1 calc R . . H22B H 0.5459 0.4377 -0.1413 0.220 Uiso 1 1 calc R . . H22C H 0.5404 0.5333 -0.0846 0.220 Uiso 1 1 calc R . . H100 H 0.764(6) 0.295(7) 0.159(3) 0.05(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.077(5) 0.033(4) 0.076(5) 0.000(4) 0.019(4) -0.003(4) N2 0.074(7) 0.128(9) 0.119(9) -0.024(6) -0.005(6) 0.003(7) N3 0.103(8) 0.082(7) 0.088(8) 0.025(5) 0.011(7) 0.004(6) C1 0.056(6) 0.047(6) 0.069(7) -0.013(5) 0.019(6) 0.000(5) C2 0.053(6) 0.050(6) 0.066(7) -0.001(5) 0.009(6) -0.008(5) C3 0.093(8) 0.044(6) 0.053(7) 0.007(5) 0.002(6) 0.010(6) C4 0.095(8) 0.069(7) 0.069(7) 0.004(6) 0.012(6) -0.003(7) N1 0.088(6) 0.046(5) 0.067(6) -0.001(4) 0.010(5) 0.004(4) C5 0.141(10) 0.059(8) 0.100(9) -0.011(6) 0.039(8) -0.017(7) C6 0.126(8) 0.038(6) 0.070(7) -0.008(5) 0.023(6) 0.006(6) C7 0.059(7) 0.053(6) 0.054(7) 0.007(5) 0.001(6) -0.002(6) C8 0.085(8) 0.051(6) 0.073(7) -0.020(6) 0.004(7) 0.021(6) C9 0.080(8) 0.082(7) 0.064(7) -0.022(6) 0.010(6) -0.001(7) C10 0.058(7) 0.061(7) 0.070(8) 0.004(6) 0.015(6) 0.012(6) C11 0.061(7) 0.069(7) 0.078(7) -0.012(6) 0.001(7) -0.015(6) C12 0.065(7) 0.052(6) 0.066(7) -0.006(5) 0.020(5) 0.004(5) C13 0.061(7) 0.141(10) 0.143(10) -0.029(8) 0.023(7) 0.006(8) C14 0.082(9) 0.113(10) 0.149(11) -0.003(8) -0.019(8) -0.003(7) C15 0.078(7) 0.049(6) 0.043(6) -0.002(5) 0.009(6) 0.005(6) C16 0.066(7) 0.056(6) 0.073(7) 0.004(6) 0.010(6) 0.012(6) C17 0.100(9) 0.053(6) 0.060(8) 0.011(6) 0.027(6) 0.003(6) C18 0.082(8) 0.060(7) 0.066(8) 0.000(6) -0.001(7) 0.022(7) C19 0.079(8) 0.110(9) 0.076(8) 0.004(7) 0.011(7) -0.001(7) C20 0.053(7) 0.086(8) 0.086(8) 0.005(7) 0.003(6) -0.005(6) C21 0.154(11) 0.121(9) 0.104(10) 0.031(8) -0.002(8) -0.025(9) C22 0.137(10) 0.187(13) 0.110(10) 0.042(8) -0.022(9) 0.031(10) _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 C1 1.440(9) . ? N2 C10 1.388(12) . ? N2 C14 1.413(9) . ? N2 C13 1.440(10) . ? N3 C18 1.409(8) . ? N3 C21 1.426(10) . ? N3 C22 1.430(12) . ? C1 C2 1.560(8) . ? C1 C15 1.565(9) . ? C1 C7 1.583(13) . ? C2 C3 1.3900 . ? C2 C6 1.3900 . ? C3 C4 1.3900 . ? C4 N1 1.3900 . ? N1 C5 1.3900 . ? C5 C6 1.3900 . ? C7 C8 1.3900 . ? C7 C12 1.3900 . ? C8 C9 1.3900 . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? 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 C10 N2 C14 122.3(8) . . ? C10 N2 C13 121.1(9) . . ? C14 N2 C13 116.5(9) . . ? C18 N3 C21 120.1(9) . . ? C18 N3 C22 120.1(9) . . ? C21 N3 C22 116.4(9) . . ? O1 C1 C2 104.9(6) . . ? O1 C1 C15 108.2(6) . . ? C2 C1 C15 111.2(6) . . ? O1 C1 C7 110.7(7) . . ? C2 C1 C7 107.7(6) . . ? C15 C1 C7 113.8(6) . . ? C3 C2 C6 120.0 . . ? C3 C2 C1 118.1(6) . . ? C6 C2 C1 121.5(6) . . ? C4 C3 C2 120.0 . . ? C3 C4 N1 120.0 . . ? C5 N1 C4 120.0 . . ? N1 C5 C6 120.0 . . ? C5 C6 C2 120.0 . . ? C8 C7 C12 120.0 . . ? C8 C7 C1 118.8(7) . . ? C12 C7 C1 121.2(6) . . ? C9 C8 C7 120.0 . . ? C8 C9 C10 120.0 . . ? N2 C10 C11 120.3(7) . . ? N2 C10 C9 119.7(7) . . ? C11 C10 C9 120.0 . . ? C10 C11 C12 120.0 . . ? C11 C12 C7 120.0 . . ? C16 C15 C20 120.0 . . ? C16 C15 C1 122.6(7) . . ? C20 C15 C1 117.3(7) . . ? C17 C16 C15 120.0 . . ? C16 C17 C18 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 N3 120.4(8) . . ? C17 C18 N3 119.6(7) . . ? C20 C19 C18 120.0 . . ? C19 C20 C15 120.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H100 N1 0.89(6) 2.00(6) 2.893(9) 174(6) 1_565 C13 H13B O1 0.96 2.55 3.44(2) 154.8 1_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 60.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.181 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.036 #===END data_beta-PG _database_code_depnum_ccdc_archive 'CCDC 285206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N3 O' _chemical_formula_weight 347.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 16.979(2) _cell_length_b 7.706(8) _cell_length_c 31.237(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.076(2) _cell_angle_gamma 90.00 _cell_volume 3997(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour white _exptl_crystal_size_max .17 _exptl_crystal_size_mid .11 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 'CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12329 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 20.83 _reflns_number_total 2102 _reflns_number_gt 1699 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+1.3280P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2102 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 N1 N 0.6964(2) 0.1270(4) 0.79938(9) 0.0779(10) Uani 1 1 d . . . N2 N 0.74584(17) -0.0260(4) 0.50123(8) 0.0579(8) Uani 1 1 d . . . N3 N 0.49004(18) 0.7705(3) 0.60015(9) 0.0577(8) Uani 1 1 d . . . O1 O 0.47186(12) 0.1383(3) 0.60649(7) 0.0483(6) Uani 1 1 d . . . C1 C 0.54855(17) 0.2247(4) 0.61731(9) 0.0402(8) Uani 1 1 d . . . C2 C 0.58652(17) 0.2005(4) 0.66596(9) 0.0406(8) Uani 1 1 d . . . C3 C 0.5712(2) 0.0572(4) 0.68894(11) 0.0583(10) Uani 1 1 d . . . H3 H 0.5359 -0.0267 0.6746 0.070 Uiso 1 1 calc R . . C4 C 0.6062(2) 0.0327(5) 0.73273(11) 0.0690(11) Uani 1 1 d . . . H4 H 0.5936 -0.0662 0.7470 0.083 Uiso 1 1 calc R . . C5 C 0.6597(2) 0.1527(5) 0.75569(10) 0.0550(9) Uani 1 1 d . . . C6 C 0.6763(2) 0.2952(5) 0.73251(11) 0.0673(11) Uani 1 1 d . . . H6 H 0.7129 0.3778 0.7464 0.081 Uiso 1 1 calc R . . C7 C 0.60250(17) 0.1574(3) 0.58738(9) 0.0387(8) Uani 1 1 d . . . C8 C 0.68105(18) 0.1051(4) 0.60202(10) 0.0456(8) Uani 1 1 d . . . H8 H 0.7030 0.1100 0.6319 0.055 Uiso 1 1 calc R . . C9 C 0.72859(19) 0.0456(4) 0.57426(10) 0.0497(9) Uani 1 1 d . . . H9 H 0.7813 0.0114 0.5858 0.060 Uiso 1 1 calc R . . C10 C 0.69877(18) 0.0359(4) 0.52899(9) 0.0437(8) Uani 1 1 d . . . C11 C 0.61910(19) 0.0877(4) 0.51414(10) 0.0482(9) Uani 1 1 d . . . H11 H 0.5966 0.0823 0.4844 0.058 Uiso 1 1 calc R . . C12 C 0.57306(18) 0.1466(4) 0.54241(9) 0.0462(8) Uani 1 1 d . . . H12 H 0.5202 0.1805 0.5311 0.055 Uiso 1 1 calc R . . C13 C 0.52770(17) 0.4164(4) 0.60955(9) 0.0400(8) Uani 1 1 d . . . C14 C 0.5689(2) 0.5274(4) 0.58790(10) 0.0538(9) Uani 1 1 d . . . H14 H 0.6108 0.4855 0.5758 0.065 Uiso 1 1 calc R . . C15 C 0.5486(2) 0.7012(4) 0.58396(11) 0.0609(10) Uani 1 1 d . . . H15 H 0.5779 0.7731 0.5691 0.073 Uiso 1 1 calc R . . C17 C 0.4497(2) 0.6623(5) 0.62057(11) 0.0609(10) Uani 1 1 d . . . H17 H 0.4076 0.7072 0.6320 0.073 Uiso 1 1 calc R . . C18 C 0.4660(2) 0.4887(4) 0.62597(11) 0.0560(9) Uani 1 1 d . . . H18 H 0.4353 0.4197 0.6407 0.067 Uiso 1 1 calc R . . C19 C 0.7415(3) 0.2653(6) 0.82319(13) 0.1078(16) Uani 1 1 d . . . H19A H 0.7838 0.2996 0.8088 0.162 Uiso 1 1 calc R . . H19B H 0.7646 0.2270 0.8524 0.162 Uiso 1 1 calc R . . H19C H 0.7066 0.3622 0.8244 0.162 Uiso 1 1 calc R . . C20 C 0.6664(3) -0.0053(7) 0.82425(13) 0.1045(16) Uani 1 1 d . . . H20A H 0.6133 0.0256 0.8278 0.157 Uiso 1 1 calc R . . H20B H 0.7015 -0.0157 0.8525 0.157 Uiso 1 1 calc R . . H20C H 0.6642 -0.1141 0.8091 0.157 Uiso 1 1 calc R . . C21 C 0.7176(2) -0.0128(5) 0.45403(11) 0.0717(11) Uani 1 1 d . . . H21A H 0.6629 -0.0525 0.4462 0.108 Uiso 1 1 calc R . . H21B H 0.7509 -0.0831 0.4396 0.108 Uiso 1 1 calc R . . H21C H 0.7204 0.1059 0.4452 0.108 Uiso 1 1 calc R . . C22 C 0.8309(2) -0.0537(5) 0.51631(12) 0.0667(10) Uani 1 1 d . . . H22A H 0.8576 0.0563 0.5219 0.100 Uiso 1 1 calc R . . H22B H 0.8517 -0.1149 0.4943 0.100 Uiso 1 1 calc R . . H22C H 0.8401 -0.1208 0.5428 0.100 Uiso 1 1 calc R . . C23 C 0.6397(2) 0.3178(4) 0.68910(11) 0.0631(10) Uani 1 1 d . . . H23 H 0.6516 0.4173 0.6748 0.076 Uiso 1 1 calc R . . H1O H 0.481(2) 0.036(5) 0.6034(11) 0.064(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.092(2) 0.094(2) 0.0428(19) 0.0028(17) 0.0022(17) -0.0101(19) N2 0.0572(19) 0.073(2) 0.0449(17) -0.0048(14) 0.0131(14) 0.0040(15) N3 0.0643(19) 0.0375(17) 0.0672(19) -0.0048(14) 0.0044(16) 0.0013(15) O1 0.0465(14) 0.0363(14) 0.0598(14) -0.0029(11) 0.0061(10) -0.0029(11) C1 0.0390(18) 0.0327(17) 0.0477(19) -0.0003(14) 0.0063(14) -0.0035(14) C2 0.0419(18) 0.0357(18) 0.0447(19) -0.0021(15) 0.0107(14) -0.0026(14) C3 0.066(2) 0.055(2) 0.050(2) 0.0027(17) 0.0028(17) -0.0165(17) C4 0.081(3) 0.071(3) 0.053(2) 0.0150(19) 0.011(2) -0.016(2) C5 0.057(2) 0.065(2) 0.042(2) -0.0034(18) 0.0092(17) -0.0010(18) C6 0.079(3) 0.059(2) 0.056(2) -0.0032(18) -0.005(2) -0.0168(19) C7 0.0419(19) 0.0296(17) 0.0426(19) 0.0015(13) 0.0046(15) 0.0005(14) C8 0.051(2) 0.0465(19) 0.0368(17) -0.0004(14) 0.0049(16) 0.0001(16) C9 0.045(2) 0.055(2) 0.047(2) 0.0023(15) 0.0042(16) 0.0039(16) C10 0.049(2) 0.0388(18) 0.043(2) 0.0001(14) 0.0090(16) -0.0033(15) C11 0.057(2) 0.050(2) 0.0351(18) 0.0021(14) 0.0030(16) 0.0018(16) C12 0.0458(19) 0.0449(19) 0.044(2) 0.0015(15) 0.0002(16) 0.0064(15) C13 0.0423(19) 0.0351(18) 0.0401(17) -0.0024(14) 0.0027(14) -0.0021(15) C14 0.065(2) 0.038(2) 0.064(2) 0.0019(16) 0.0248(18) 0.0039(16) C15 0.077(3) 0.040(2) 0.070(2) 0.0057(17) 0.024(2) -0.0026(19) C17 0.057(2) 0.046(2) 0.081(3) -0.0095(19) 0.0198(19) 0.0047(18) C18 0.059(2) 0.041(2) 0.072(2) -0.0035(16) 0.0240(18) -0.0007(16) C19 0.137(4) 0.106(4) 0.061(3) -0.011(2) -0.024(3) -0.006(3) C20 0.096(3) 0.160(5) 0.056(2) 0.032(3) 0.013(2) -0.013(3) C21 0.083(3) 0.083(3) 0.052(2) -0.0075(19) 0.0210(19) -0.005(2) C22 0.062(3) 0.074(3) 0.068(2) -0.0027(19) 0.0233(19) 0.0027(19) C23 0.078(2) 0.050(2) 0.054(2) 0.0076(17) -0.0019(19) -0.0165(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.391(4) . ? N1 C19 1.427(5) . ? N1 C20 1.439(5) . ? N2 C10 1.382(4) . ? N2 C22 1.438(4) . ? N2 C21 1.455(4) . ? N3 C15 1.320(4) . ? N3 C17 1.324(4) . ? O1 C1 1.438(3) . ? C1 C13 1.526(4) . ? C1 C7 1.530(4) . ? C1 C2 1.533(4) . ? C2 C23 1.371(4) . ? C2 C3 1.372(4) . ? C3 C4 1.386(5) . ? C4 C5 1.386(5) . ? C5 C6 1.377(5) . ? C6 C23 1.379(4) . ? C7 C8 1.377(4) . ? C7 C12 1.391(4) . ? C8 C9 1.381(4) . ? C9 C10 1.400(4) . ? C10 C11 1.394(4) . ? C11 C12 1.373(4) . ? C13 C14 1.370(4) . ? C13 C18 1.378(4) . ? C14 C15 1.382(5) . ? C17 C18 1.369(5) . ? 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 N1 C19 119.1(3) . . ? C5 N1 C20 119.6(3) . . ? C19 N1 C20 117.4(3) . . ? C10 N2 C22 121.2(3) . . ? C10 N2 C21 120.0(3) . . ? C22 N2 C21 116.0(3) . . ? C15 N3 C17 115.9(3) . . ? O1 C1 C13 104.0(2) . . ? O1 C1 C7 109.1(2) . . ? C13 C1 C7 112.3(2) . . ? O1 C1 C2 110.4(2) . . ? C13 C1 C2 108.1(2) . . ? C7 C1 C2 112.5(2) . . ? C23 C2 C3 115.5(3) . . ? C23 C2 C1 122.4(3) . . ? C3 C2 C1 122.0(3) . . ? C2 C3 C4 122.5(3) . . ? C5 C4 C3 121.3(3) . . ? C6 C5 C4 116.4(3) . . ? C6 C5 N1 122.0(3) . . ? C4 C5 N1 121.6(3) . . ? C5 C6 C23 121.1(3) . . ? C8 C7 C12 115.9(3) . . ? C8 C7 C1 124.0(2) . . ? C12 C7 C1 120.2(2) . . ? C7 C8 C9 122.8(3) . . ? C8 C9 C10 121.1(3) . . ? N2 C10 C11 122.6(3) . . ? N2 C10 C9 121.2(3) . . ? C11 C10 C9 116.2(3) . . ? C12 C11 C10 121.6(3) . . ? C11 C12 C7 122.4(3) . . ? C14 C13 C18 116.0(3) . . ? C14 C13 C1 123.9(3) . . ? C18 C13 C1 120.1(3) . . ? C13 C14 C15 120.4(3) . . ? N3 C15 C14 123.5(3) . . ? N3 C17 C18 124.3(3) . . ? C17 C18 C13 119.9(3) . . ? C2 C23 C6 123.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N3 0.81(4) 2.06(4) 2.862(5) 172(3) 1_545 C21 H21A O1 0.96 2.61 3.509(4) 156.4 5_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 20.83 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.655 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.050 #===END data_gamma-PG _database_code_depnum_ccdc_archive 'CCDC 285207' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N3 O' _chemical_formula_weight 347.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.759(9) _cell_length_b 18.66(2) _cell_length_c 6.570(5) _cell_angle_alpha 96.20(10) _cell_angle_beta 97.72(9) _cell_angle_gamma 96.10(10) _cell_volume 930.0(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max .12 _exptl_crystal_size_mid .09 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.606 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CAD4 diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2759 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1647 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 23.53 _reflns_number_total 2759 _reflns_number_gt 713 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2759 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2543 _refine_ls_R_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.3649 _refine_ls_wR_factor_gt 0.2762 _refine_ls_goodness_of_fit_ref 0.799 _refine_ls_restrained_S_all 0.799 _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 0.3480(9) 0.2559(3) 0.0541(9) 0.079(2) Uani 1 1 d . . . N1 N 0.9769(11) 0.2669(4) -0.0014(16) 0.089(3) Uani 1 1 d . . . N2 N 0.2241(11) 0.5014(5) -0.5163(14) 0.088(3) Uani 1 1 d . . . N3 N 0.2217(11) -0.0382(4) -0.5697(13) 0.095(3) Uani 1 1 d . . . C1 C 0.4092(12) 0.2511(5) -0.1429(14) 0.071(3) Uani 1 1 d . . . C2 C 0.3579(12) 0.3131(5) -0.2519(15) 0.070(3) Uani 1 1 d . . . C3 C 0.3888(14) 0.3839(6) -0.1426(15) 0.090(3) Uani 1 1 d . . . H3 H 0.4397 0.3897 -0.0045 0.108 Uiso 1 1 calc R . . C4 C 0.3479(14) 0.4431(6) -0.2292(18) 0.090(3) Uani 1 1 d . . . H4 H 0.3772 0.4881 -0.1491 0.108 Uiso 1 1 calc R . . C5 C 0.2638(13) 0.4412(5) -0.4329(17) 0.075(3) Uani 1 1 d . . . C6 C 0.2271(13) 0.3710(6) -0.5481(15) 0.083(3) Uani 1 1 d . . . H6 H 0.1734 0.3650 -0.6852 0.100 Uiso 1 1 calc R . . C7 C 0.2720(13) 0.3120(5) -0.4542(16) 0.081(3) Uani 1 1 d . . . H7 H 0.2424 0.2667 -0.5326 0.098 Uiso 1 1 calc R . . C8 C 0.3527(12) 0.1756(5) -0.2616(13) 0.074(3) Uani 1 1 d . . . C9 C 0.2681(13) 0.1201(5) -0.1709(14) 0.087(3) Uani 1 1 d . . . H9 H 0.2375 0.1309 -0.0399 0.105 Uiso 1 1 calc R . . C10 C 0.2282(14) 0.0495(5) -0.2693(16) 0.097(4) Uani 1 1 d . . . H10 H 0.1756 0.0141 -0.2003 0.117 Uiso 1 1 calc R . . C11 C 0.2642(13) 0.0301(5) -0.4669(15) 0.085(3) Uani 1 1 d . . . C12 C 0.3519(15) 0.0851(5) -0.5598(15) 0.104(4) Uani 1 1 d . . . H12 H 0.3822 0.0741 -0.6909 0.124 Uiso 1 1 calc R . . C13 C 0.3934(13) 0.1547(5) -0.4599(14) 0.086(3) Uani 1 1 d . . . H13 H 0.4509 0.1896 -0.5265 0.103 Uiso 1 1 calc R . . C14 C 0.6066(14) 0.2590(5) -0.0888(17) 0.078(3) Uani 1 1 d . . . C15 C 0.7215(15) 0.2834(5) -0.2216(15) 0.087(3) Uani 1 1 d . . . H15 H 0.6749 0.2981 -0.3460 0.105 Uiso 1 1 calc R . . C16 C 0.8988(15) 0.2864(6) -0.1748(18) 0.086(3) Uani 1 1 d . . . H16 H 0.9681 0.3028 -0.2693 0.103 Uiso 1 1 calc R . . C17 C 0.8675(15) 0.2438(5) 0.1250(16) 0.088(3) Uani 1 1 d . . . H17 H 0.9186 0.2307 0.2497 0.106 Uiso 1 1 calc R . . C18 C 0.6937(15) 0.2375(5) 0.0915(15) 0.078(3) Uani 1 1 d . . . H18 H 0.6296 0.2187 0.1878 0.093 Uiso 1 1 calc R . . C19 C 0.1643(16) -0.0979(5) -0.4563(17) 0.118(4) Uani 1 1 d . . . H19A H 0.1679 -0.1435 -0.5377 0.177 Uiso 1 1 calc R . . H19B H 0.0467 -0.0942 -0.4298 0.177 Uiso 1 1 calc R . . H19C H 0.2408 -0.0951 -0.3274 0.177 Uiso 1 1 calc R . . C20 C 0.2503(15) -0.0568(5) -0.7802(16) 0.108(4) Uani 1 1 d . . . H20A H 0.2048 -0.1067 -0.8258 0.162 Uiso 1 1 calc R . . H20B H 0.3737 -0.0500 -0.7873 0.162 Uiso 1 1 calc R . . H20C H 0.1916 -0.0261 -0.8677 0.162 Uiso 1 1 calc R . . C21 C 0.2634(14) 0.5733(5) -0.4013(15) 0.103(4) Uani 1 1 d . . . H21A H 0.2066 0.6073 -0.4783 0.155 Uiso 1 1 calc R . . H21B H 0.3878 0.5873 -0.3791 0.155 Uiso 1 1 calc R . . H21C H 0.2218 0.5729 -0.2701 0.155 Uiso 1 1 calc R . . C22 C 0.1638(16) 0.5008(6) -0.7344(18) 0.110(4) Uani 1 1 d . . . H22A H 0.1657 0.5499 -0.7666 0.165 Uiso 1 1 calc R . . H22B H 0.0464 0.4765 -0.7679 0.165 Uiso 1 1 calc R . . H22C H 0.2394 0.4758 -0.8137 0.165 Uiso 1 1 calc R . . H100 H 0.216(10) 0.248(4) 0.038(10) 0.06(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.074(5) 0.079(4) 0.084(5) -0.007(3) 0.033(4) -0.003(4) N1 0.089(7) 0.073(5) 0.108(7) -0.008(5) 0.042(6) 0.007(5) N2 0.106(7) 0.072(6) 0.087(7) 0.006(5) 0.026(5) 0.012(5) N3 0.124(8) 0.061(5) 0.099(6) -0.007(5) 0.026(5) 0.007(5) C1 0.072(7) 0.063(6) 0.078(7) -0.010(5) 0.032(5) -0.001(5) C2 0.075(7) 0.078(7) 0.057(6) -0.002(5) 0.023(5) 0.001(5) C3 0.111(9) 0.083(8) 0.074(7) -0.007(6) 0.018(6) 0.005(7) C4 0.115(10) 0.067(7) 0.087(8) -0.001(6) 0.023(7) 0.015(6) C5 0.079(7) 0.067(7) 0.087(8) 0.011(6) 0.033(6) 0.017(6) C6 0.083(8) 0.086(8) 0.076(7) -0.008(6) 0.020(6) -0.005(6) C7 0.091(8) 0.068(7) 0.089(8) -0.002(6) 0.043(7) -0.001(6) C8 0.091(7) 0.060(6) 0.073(6) -0.009(5) 0.036(5) 0.008(5) C9 0.099(8) 0.081(7) 0.087(7) 0.001(6) 0.044(6) 0.001(6) C10 0.127(10) 0.066(7) 0.095(8) -0.008(6) 0.039(7) -0.017(6) C11 0.106(9) 0.059(6) 0.088(7) -0.010(6) 0.028(6) -0.005(6) C12 0.164(11) 0.063(6) 0.082(7) -0.027(5) 0.058(7) -0.011(7) C13 0.103(8) 0.063(6) 0.095(7) -0.002(5) 0.047(6) 0.002(5) C14 0.083(8) 0.058(6) 0.093(8) -0.014(5) 0.038(7) 0.006(5) C15 0.088(9) 0.090(7) 0.088(7) 0.007(5) 0.037(7) 0.005(6) C16 0.063(8) 0.117(9) 0.082(8) 0.017(6) 0.019(6) 0.016(6) C17 0.078(9) 0.092(8) 0.090(8) -0.001(6) 0.013(7) 0.003(6) C18 0.075(8) 0.080(7) 0.076(8) 0.004(5) 0.018(6) 0.001(6) C19 0.147(11) 0.072(7) 0.140(10) 0.001(7) 0.052(9) 0.006(7) C20 0.136(10) 0.075(7) 0.109(9) -0.018(6) 0.038(7) 0.004(7) C21 0.124(10) 0.064(7) 0.118(9) -0.005(6) 0.027(7) -0.006(6) C22 0.138(11) 0.089(8) 0.109(9) 0.013(7) 0.039(8) 0.014(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 C1 1.434(9) . ? N1 C16 1.322(11) . ? N1 C17 1.336(11) . ? N2 C5 1.348(11) . ? N2 C22 1.445(11) . ? N2 C21 1.447(11) . ? N3 C11 1.361(11) . ? N3 C20 1.441(11) . ? N3 C19 1.470(12) . ? C1 C2 1.487(12) . ? C1 C14 1.513(13) . ? C1 C8 1.525(11) . ? C2 C7 1.401(12) . ? C2 C3 1.413(12) . ? C3 C4 1.344(12) . ? C4 C5 1.403(12) . ? C5 C6 1.422(12) . ? C6 C7 1.373(12) . ? C8 C9 1.396(11) . ? C8 C13 1.406(11) . ? C9 C10 1.389(12) . ? C10 C11 1.383(12) . ? C11 C12 1.409(12) . ? C12 C13 1.377(11) . ? C14 C18 1.403(12) . ? C14 C15 1.404(12) . ? C15 C16 1.362(13) . ? C17 C18 1.327(12) . ? 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 C16 N1 C17 114.4(10) . . ? C5 N2 C22 122.7(9) . . ? C5 N2 C21 122.5(9) . . ? C22 N2 C21 114.2(9) . . ? C11 N3 C20 122.9(9) . . ? C11 N3 C19 119.3(9) . . ? C20 N3 C19 117.4(8) . . ? O1 C1 C2 109.3(7) . . ? O1 C1 C14 104.1(8) . . ? C2 C1 C14 109.3(8) . . ? O1 C1 C8 110.4(7) . . ? C2 C1 C8 116.1(8) . . ? C14 C1 C8 107.0(7) . . ? C7 C2 C3 112.3(10) . . ? C7 C2 C1 128.7(9) . . ? C3 C2 C1 119.0(9) . . ? C4 C3 C2 123.0(10) . . ? C3 C4 C5 124.0(10) . . ? N2 C5 C4 123.0(10) . . ? N2 C5 C6 122.0(11) . . ? C4 C5 C6 115.0(10) . . ? C7 C6 C5 119.1(10) . . ? C6 C7 C2 126.5(9) . . ? C9 C8 C13 115.2(8) . . ? C9 C8 C1 121.3(8) . . ? C13 C8 C1 123.4(8) . . ? C10 C9 C8 122.3(8) . . ? C11 C10 C9 122.0(9) . . ? N3 C11 C10 123.3(9) . . ? N3 C11 C12 120.2(9) . . ? C10 C11 C12 116.5(9) . . ? C13 C12 C11 121.1(9) . . ? C12 C13 C8 122.9(9) . . ? C18 C14 C15 112.9(10) . . ? C18 C14 C1 123.5(9) . . ? C15 C14 C1 123.4(11) . . ? C16 C15 C14 122.4(11) . . ? N1 C16 C15 123.1(10) . . ? C18 C17 N1 127.0(11) . . ? C17 C18 C14 120.1(10) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H100 N1 1.01(7) 1.91(8) 2.885(11) 160(6) 1_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.424 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.104