# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Philip Page' 'Steven Allin' 'Mark R. J. Elsegood' 'P. Maddocks' _publ_contact_author_name 'Prof Philip Page' _publ_contact_author_address ; Department of Chemistry Loughborough University Loughborough Leicestershire LE11 3TU UNITED KINGDOM ; _publ_contact_author_email P.C.B.PAGE@LBORO.AC.UK _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; New ligands for asymmetric diethylzinc additions to aromatic aldehdes, demonstrating substrate-dependent nonlinear effects ; data_3c _database_code_CSD 198143 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H25 N O' _chemical_formula_weight 391.49 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.7982(9) _cell_length_b 21.474(3) _cell_length_c 8.7813(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.221(2) _cell_angle_gamma 90.00 _cell_volume 1049.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3694 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.67 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details 'SADABS, Sheldrick, G.M.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7934 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.67 _reflns_number_total 4416 _reflns_number_gt 3726 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0666P)^2^+0.0357P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 4416 _refine_ls_number_parameters 284 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.6523(3) 0.41598(9) 0.0771(2) 0.0257(5) Uani 0.693(4) 1 d P A 1 C1 C 0.6668(6) 0.38003(12) 0.2237(3) 0.0430(6) Uani 1 1 d . . . H1A H 0.8277 0.3732 0.2984 0.052 Uiso 1 1 calc R A 1 H1B H 0.5350 0.3851 0.2741 0.052 Uiso 1 1 calc R A 1 C2 C 0.6109(4) 0.34825(10) 0.0677(2) 0.0254(5) Uani 0.693(4) 1 d P A 1 H2 H 0.4413 0.3341 0.0218 0.031 Uiso 0.693(4) 1 calc PR A 1 C2X C 0.6523(3) 0.41598(9) 0.0771(2) 0.0257(5) Uani 0.31 1 d P A 2 H2X H 0.8065 0.4315 0.0611 0.031 Uiso 0.307(4) 1 calc PR A 2 N1X N 0.6109(4) 0.34825(10) 0.0677(2) 0.0254(5) Uani 0.31 1 d P A 2 C3 C 0.8029(3) 0.30974(10) 0.0280(2) 0.0228(4) Uani 1 1 d . . . H3 H 0.9585 0.3327 0.0662 0.027 Uiso 0.307(4) 1 calc PR A 2 O1 O 1.0173(4) 0.34507(11) 0.0795(3) 0.0277(6) Uani 0.693(4) 1 d P A 1 H1 H 0.9863 0.3829 0.0598 0.042 Uiso 0.693(4) 1 calc PR A 1 C4 C 0.7553(4) 0.29853(9) -0.1506(2) 0.0223(4) Uani 1 1 d . A . C5 C 0.5435(4) 0.31503(11) -0.2626(3) 0.0292(5) Uani 1 1 d . . . H5 H 0.4184 0.3345 -0.2296 0.035 Uiso 1 1 calc R A . C6 C 0.5130(5) 0.30316(12) -0.4229(3) 0.0352(5) Uani 1 1 d . A . H6 H 0.3674 0.3149 -0.4983 0.042 Uiso 1 1 calc R . . C7 C 0.6904(4) 0.27483(12) -0.4729(3) 0.0346(5) Uani 1 1 d . . . H7 H 0.6679 0.2668 -0.5825 0.042 Uiso 1 1 calc R A . C8 C 0.9037(4) 0.25793(12) -0.3623(3) 0.0336(5) Uani 1 1 d . A . H8 H 1.0278 0.2382 -0.3959 0.040 Uiso 1 1 calc R . . C9 C 0.9345(4) 0.27002(11) -0.2028(3) 0.0294(5) Uani 1 1 d . . . H9 H 1.0809 0.2586 -0.1278 0.035 Uiso 1 1 calc R A . C10 C 0.8278(4) 0.24817(10) 0.1169(2) 0.0240(4) Uani 1 1 d . A . C11 C 1.0465(4) 0.22906(12) 0.2170(3) 0.0321(5) Uani 1 1 d . . . H11 H 1.1847 0.2546 0.2311 0.038 Uiso 1 1 calc R A . C12 C 1.0633(5) 0.17219(13) 0.2973(3) 0.0398(6) Uani 1 1 d . A . H12 H 1.2141 0.1588 0.3637 0.048 Uiso 1 1 calc R . . C13 C 0.8632(5) 0.13553(13) 0.2808(3) 0.0401(6) Uani 1 1 d . . . H13 H 0.8751 0.0974 0.3372 0.048 Uiso 1 1 calc R A . C14 C 0.6454(5) 0.15438(11) 0.1822(3) 0.0353(6) Uani 1 1 d . A . H14 H 0.5070 0.1291 0.1704 0.042 Uiso 1 1 calc R . . C15 C 0.6274(4) 0.21029(11) 0.0998(3) 0.0287(5) Uani 1 1 d . . . H15 H 0.4769 0.2227 0.0312 0.034 Uiso 1 1 calc R A . C16 C 0.4370(4) 0.45582(10) 0.0189(2) 0.0227(4) Uani 1 1 d . . . H16 H 0.2962 0.4330 0.0363 0.027 Uiso 0.693(4) 1 calc PR A 1 O1X O 0.2584(9) 0.4217(3) 0.0482(6) 0.0301(14) Uani 0.307(4) 1 d P A 2 H1X H 0.2808 0.3838 0.0329 0.045 Uiso 0.307(4) 1 calc PR A 2 C17 C 0.3893(4) 0.46682(10) -0.1583(2) 0.0230(4) Uani 1 1 d . A . C18 C 0.1718(4) 0.44952(11) -0.2628(3) 0.0311(5) Uani 1 1 d . . . H18 H 0.0510 0.4309 -0.2237 0.037 Uiso 1 1 calc R A . C19 C 0.1301(5) 0.45950(14) -0.4264(3) 0.0434(7) Uani 1 1 d . A . H19 H -0.0196 0.4479 -0.4976 0.052 Uiso 1 1 calc R . . C20 C 0.3037(5) 0.48575(15) -0.4838(3) 0.0466(7) Uani 1 1 d . . . H20 H 0.2755 0.4917 -0.5947 0.056 Uiso 1 1 calc R A . C21 C 0.5207(5) 0.50371(13) -0.3804(3) 0.0417(6) Uani 1 1 d . A . H21 H 0.6405 0.5224 -0.4203 0.050 Uiso 1 1 calc R . . C22 C 0.5632(4) 0.49433(11) -0.2179(3) 0.0303(5) Uani 1 1 d . . . H22 H 0.7121 0.5068 -0.1472 0.036 Uiso 1 1 calc R A . C23 C 0.4644(4) 0.51675(10) 0.1105(2) 0.0233(4) Uani 1 1 d . A . C24 C 0.2618(4) 0.55302(11) 0.0987(3) 0.0307(5) Uani 1 1 d . . . H24 H 0.1106 0.5392 0.0338 0.037 Uiso 1 1 calc R A . C25 C 0.2752(5) 0.60862(11) 0.1791(3) 0.0359(6) Uani 1 1 d . A . H25 H 0.1341 0.6326 0.1697 0.043 Uiso 1 1 calc R . . C26 C 0.4945(5) 0.62955(11) 0.2735(3) 0.0352(5) Uani 1 1 d . . . H26 H 0.5048 0.6680 0.3285 0.042 Uiso 1 1 calc R A . C27 C 0.6978(5) 0.59425(12) 0.2871(3) 0.0352(6) Uani 1 1 d . A . H27 H 0.8483 0.6084 0.3523 0.042 Uiso 1 1 calc R . . C28 C 0.6843(4) 0.53779(11) 0.2056(3) 0.0285(5) Uani 1 1 d . . . H28 H 0.8254 0.5138 0.2152 0.034 Uiso 1 1 calc R A . 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 0.0316(10) 0.0248(10) 0.0171(9) -0.0009(7) 0.0011(7) -0.0005(8) C1 0.0805(19) 0.0306(11) 0.0165(10) -0.0002(9) 0.0111(12) 0.0035(12) C2 0.0349(11) 0.0261(10) 0.0160(9) -0.0018(8) 0.0083(8) -0.0040(9) C2X 0.0316(10) 0.0248(10) 0.0171(9) -0.0009(7) 0.0011(7) -0.0005(8) N1X 0.0349(11) 0.0261(10) 0.0160(9) -0.0018(8) 0.0083(8) -0.0040(9) C3 0.0235(10) 0.0277(11) 0.0169(10) -0.0006(8) 0.0051(8) -0.0026(9) O1 0.0221(11) 0.0333(13) 0.0258(12) -0.0070(10) 0.0034(9) -0.0013(10) C4 0.0295(10) 0.0214(10) 0.0166(9) 0.0019(8) 0.0075(8) -0.0024(8) C5 0.0326(11) 0.0306(12) 0.0247(11) -0.0011(9) 0.0087(9) 0.0053(9) C6 0.0447(13) 0.0345(12) 0.0206(11) -0.0009(10) -0.0008(9) 0.0044(11) C7 0.0529(15) 0.0330(12) 0.0194(11) 0.0003(9) 0.0126(11) -0.0029(11) C8 0.0381(12) 0.0396(13) 0.0277(12) -0.0038(10) 0.0169(10) 0.0005(10) C9 0.0277(11) 0.0365(13) 0.0250(11) 0.0020(9) 0.0087(9) -0.0011(10) C10 0.0283(11) 0.0295(11) 0.0143(9) -0.0030(8) 0.0064(8) 0.0038(9) C11 0.0290(11) 0.0427(14) 0.0220(11) 0.0010(10) 0.0030(9) 0.0062(10) C12 0.0468(15) 0.0466(15) 0.0230(12) 0.0066(11) 0.0046(11) 0.0161(13) C13 0.0629(16) 0.0325(12) 0.0261(12) 0.0086(10) 0.0145(11) 0.0134(12) C14 0.0474(14) 0.0285(12) 0.0320(13) 0.0008(10) 0.0146(11) -0.0004(11) C15 0.0313(12) 0.0296(12) 0.0229(11) 0.0008(9) 0.0038(9) 0.0036(9) C16 0.0239(10) 0.0250(10) 0.0181(10) 0.0005(8) 0.0041(8) -0.0018(8) O1X 0.026(3) 0.034(3) 0.032(3) -0.001(2) 0.011(2) -0.007(2) C17 0.0251(10) 0.0242(11) 0.0184(10) -0.0030(8) 0.0039(8) 0.0047(8) C18 0.0297(11) 0.0314(12) 0.0272(11) -0.0055(9) -0.0001(9) 0.0020(9) C19 0.0421(14) 0.0522(16) 0.0237(12) -0.0113(11) -0.0110(10) 0.0136(12) C20 0.0637(18) 0.0583(17) 0.0148(11) 0.0006(11) 0.0057(12) 0.0207(15) C21 0.0506(15) 0.0534(16) 0.0253(12) 0.0084(11) 0.0173(11) 0.0127(12) C22 0.0319(11) 0.0370(13) 0.0211(11) 0.0021(9) 0.0058(9) 0.0017(10) C23 0.0298(11) 0.0249(10) 0.0163(9) 0.0020(8) 0.0085(8) -0.0012(9) C24 0.0302(12) 0.0319(13) 0.0306(12) 0.0008(10) 0.0095(10) 0.0026(10) C25 0.0416(14) 0.0324(13) 0.0361(14) -0.0007(10) 0.0147(11) 0.0091(11) C26 0.0573(15) 0.0253(12) 0.0278(12) -0.0053(10) 0.0197(11) 0.0000(11) C27 0.0399(13) 0.0380(13) 0.0242(12) -0.0083(10) 0.0031(10) -0.0062(11) C28 0.0344(12) 0.0296(11) 0.0201(10) -0.0025(9) 0.0054(9) 0.0030(9) _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 C2 1.473(3) . ? N1 C16 1.482(3) . ? N1 C1 1.483(3) . ? C1 C2 1.483(3) . ? C2 C3 1.504(3) . ? C3 O1 1.418(3) . ? C3 C10 1.522(3) . ? C3 C4 1.534(3) . ? C4 C5 1.387(3) . ? C4 C9 1.390(3) . ? C5 C6 1.392(3) . ? C6 C7 1.369(4) . ? C7 C8 1.391(3) . ? C8 C9 1.386(3) . ? C10 C11 1.388(3) . ? C10 C15 1.392(3) . ? C11 C12 1.400(4) . ? C12 C13 1.376(4) . ? C13 C14 1.378(4) . ? C14 C15 1.390(3) . ? C16 O1X 1.351(5) . ? C16 C17 1.521(3) . ? C16 C23 1.521(3) . ? C17 C18 1.387(3) . ? C17 C22 1.390(3) . ? C18 C19 1.405(4) . ? C19 C20 1.367(4) . ? C20 C21 1.385(4) . ? C21 C22 1.394(3) . ? C23 C24 1.389(3) . ? C23 C28 1.390(3) . ? C24 C25 1.378(3) . ? C25 C26 1.385(4) . ? C26 C27 1.378(4) . ? C27 C28 1.399(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 C2 N1 C16 116.25(17) . . ? C2 N1 C1 60.22(14) . . ? C16 N1 C1 115.99(19) . . ? C2 C1 N1 59.54(14) . . ? N1 C2 C1 60.24(15) . . ? N1 C2 C3 115.86(17) . . ? C1 C2 C3 118.83(19) . . ? O1 C3 C2 105.77(18) . . ? O1 C3 C10 110.61(18) . . ? C2 C3 C10 109.22(16) . . ? O1 C3 C4 107.55(17) . . ? C2 C3 C4 112.95(17) . . ? C10 C3 C4 110.64(17) . . ? C5 C4 C9 118.3(2) . . ? C5 C4 C3 123.73(18) . . ? C9 C4 C3 117.95(18) . . ? C4 C5 C6 120.4(2) . . ? C7 C6 C5 120.8(2) . . ? C6 C7 C8 119.5(2) . . ? C9 C8 C7 119.7(2) . . ? C8 C9 C4 121.2(2) . . ? C11 C10 C15 118.9(2) . . ? C11 C10 C3 121.40(19) . . ? C15 C10 C3 119.72(19) . . ? C10 C11 C12 120.0(2) . . ? C13 C12 C11 120.5(2) . . ? C12 C13 C14 119.7(2) . . ? C13 C14 C15 120.2(2) . . ? C14 C15 C10 120.6(2) . . ? O1X C16 N1 103.8(3) . . ? O1X C16 C17 110.5(3) . . ? N1 C16 C17 109.74(16) . . ? O1X C16 C23 109.8(3) . . ? N1 C16 C23 111.13(16) . . ? C17 C16 C23 111.72(17) . . ? C18 C17 C22 119.1(2) . . ? C18 C17 C16 120.46(19) . . ? C22 C17 C16 120.46(18) . . ? C17 C18 C19 120.0(2) . . ? C20 C19 C18 120.4(2) . . ? C19 C20 C21 120.0(2) . . ? C20 C21 C22 120.0(2) . . ? C17 C22 C21 120.5(2) . . ? C24 C23 C28 118.5(2) . . ? C24 C23 C16 118.78(19) . . ? C28 C23 C16 122.70(19) . . ? C25 C24 C23 121.5(2) . . ? C24 C25 C26 119.9(2) . . ? C27 C26 C25 119.6(2) . . ? C26 C27 C28 120.5(2) . . ? C23 C28 C27 120.0(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.84 2.11 2.603(3) 117.3 . O1X H1X N1X 0.84 2.00 2.549(6) 121.9 . _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.292 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.052 #===END data_3d _database_code_CSD 198144 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 N O' _chemical_formula_weight 389.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 25.1727(18) _cell_length_b 7.5583(6) _cell_length_c 11.0247(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.739(2) _cell_angle_gamma 90.00 _cell_volume 2093.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6797 _cell_measurement_theta_min 2.380 _cell_measurement_theta_max 28.731 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.66 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details 'SADABS, Sheldrick, G.M.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9269 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.84 _reflns_number_total 4841 _reflns_number_gt 4603 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0519P)^2^+0.6708P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(11) _refine_ls_number_reflns 4841 _refine_ls_number_parameters 273 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.39195(4) 0.32302(13) 0.48973(8) 0.0265(2) Uani 1 1 d . . . H1 H 0.3812 0.4190 0.4586 0.040 Uiso 1 1 calc R . . N1 N 0.32109(4) 0.40597(15) 0.30810(10) 0.0243(2) Uani 1 1 d . . . C1 C 0.28695(5) 0.27747(19) 0.36860(12) 0.0285(3) Uani 1 1 d . . . H1A H 0.2861 0.2838 0.4581 0.034 Uiso 1 1 calc R . . H1B H 0.2529 0.2422 0.3252 0.034 Uiso 1 1 calc R . . C2 C 0.33710(5) 0.21878(17) 0.31752(11) 0.0236(2) Uani 1 1 d . . . H2 H 0.3334 0.1478 0.2409 0.028 Uiso 1 1 calc R . . C3 C 0.38741(5) 0.18649(17) 0.40026(11) 0.0225(2) Uani 1 1 d . . . C4 C 0.43537(5) 0.18850(18) 0.32094(11) 0.0227(2) Uani 1 1 d . . . C5 C 0.47183(5) 0.3269(2) 0.32649(12) 0.0288(3) Uani 1 1 d . . . H5 H 0.4684 0.4203 0.3831 0.035 Uiso 1 1 calc R . . C6 C 0.51347(6) 0.3286(2) 0.24896(13) 0.0356(3) Uani 1 1 d . . . H6 H 0.5384 0.4232 0.2534 0.043 Uiso 1 1 calc R . . C7 C 0.51888(6) 0.1943(2) 0.16599(13) 0.0365(3) Uani 1 1 d . . . H7 H 0.5472 0.1970 0.1130 0.044 Uiso 1 1 calc R . . C8 C 0.48282(6) 0.0556(2) 0.16024(13) 0.0327(3) Uani 1 1 d . . . H8 H 0.4864 -0.0371 0.1031 0.039 Uiso 1 1 calc R . . C9 C 0.44144(5) 0.05124(18) 0.23770(12) 0.0272(3) Uani 1 1 d . . . H9 H 0.4172 -0.0452 0.2341 0.033 Uiso 1 1 calc R . . C10 C 0.38498(5) 0.01218(17) 0.46944(11) 0.0235(3) Uani 1 1 d . . . C11 C 0.42677(6) -0.02651(19) 0.55495(12) 0.0293(3) Uani 1 1 d . . . H11 H 0.4554 0.0545 0.5677 0.035 Uiso 1 1 calc R . . C12 C 0.42670(6) -0.1826(2) 0.62157(13) 0.0338(3) Uani 1 1 d . . . H12 H 0.4554 -0.2081 0.6792 0.041 Uiso 1 1 calc R . . C13 C 0.38487(6) -0.30108(19) 0.60402(13) 0.0316(3) Uani 1 1 d . . . H13 H 0.3846 -0.4070 0.6503 0.038 Uiso 1 1 calc R . . C14 C 0.34346(6) -0.26466(18) 0.51887(13) 0.0306(3) Uani 1 1 d . . . H14 H 0.3149 -0.3462 0.5064 0.037 Uiso 1 1 calc R . . C15 C 0.34347(5) -0.10879(18) 0.45129(12) 0.0273(3) Uani 1 1 d . . . H15 H 0.3150 -0.0850 0.3926 0.033 Uiso 1 1 calc R . . C16 C 0.29926(5) 0.46721(17) 0.18844(11) 0.0243(3) Uani 1 1 d . . . H16 H 0.2818 0.3664 0.1427 0.029 Uiso 1 1 calc R . . C17 C 0.34091(5) 0.55202(19) 0.11265(11) 0.0259(3) Uani 1 1 d . . . C18 C 0.38791(5) 0.4813(2) 0.07429(12) 0.0315(3) Uani 1 1 d . . . H18 H 0.3991 0.3658 0.0985 0.038 Uiso 1 1 calc R . . C19 C 0.41832(6) 0.5839(2) -0.00083(13) 0.0368(3) Uani 1 1 d . . . H19 H 0.4509 0.5381 -0.0266 0.044 Uiso 1 1 calc R . . C20 C 0.40181(6) 0.7511(2) -0.03827(13) 0.0377(3) Uani 1 1 d . . . H20 H 0.4227 0.8172 -0.0908 0.045 Uiso 1 1 calc R . . C21 C 0.35484(6) 0.8232(2) 0.00042(12) 0.0326(3) Uani 1 1 d . . . H21 H 0.3435 0.9380 -0.0251 0.039 Uiso 1 1 calc R . . C22 C 0.32491(5) 0.72319(18) 0.07733(11) 0.0264(3) Uani 1 1 d . . . C23 C 0.27464(5) 0.76441(18) 0.13261(11) 0.0256(3) Uani 1 1 d . . . C24 C 0.24395(6) 0.9176(2) 0.12723(12) 0.0305(3) Uani 1 1 d . . . H24 H 0.2541 1.0168 0.0811 0.037 Uiso 1 1 calc R . . C25 C 0.19798(6) 0.9220(2) 0.19104(13) 0.0347(3) Uani 1 1 d . . . H25 H 0.1766 1.0255 0.1885 0.042 Uiso 1 1 calc R . . C26 C 0.18305(6) 0.7769(2) 0.25835(13) 0.0364(3) Uani 1 1 d . . . H26 H 0.1517 0.7829 0.3018 0.044 Uiso 1 1 calc R . . C27 C 0.21355(6) 0.6223(2) 0.26283(13) 0.0311(3) Uani 1 1 d . . . H27 H 0.2031 0.5228 0.3082 0.037 Uiso 1 1 calc R . . C28 C 0.25953(5) 0.61718(18) 0.19960(12) 0.0255(3) Uani 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 0.0338(5) 0.0213(4) 0.0245(4) -0.0024(4) 0.0014(3) 0.0025(4) N1 0.0250(5) 0.0254(5) 0.0227(5) 0.0023(4) 0.0029(4) 0.0026(4) C1 0.0249(6) 0.0315(7) 0.0295(6) 0.0063(5) 0.0051(5) 0.0024(5) C2 0.0237(6) 0.0234(6) 0.0237(6) 0.0009(5) 0.0016(4) 0.0013(5) C3 0.0244(6) 0.0216(6) 0.0213(5) -0.0008(5) 0.0011(4) -0.0003(5) C4 0.0216(5) 0.0255(6) 0.0208(5) 0.0043(5) -0.0006(4) 0.0013(5) C5 0.0295(6) 0.0286(6) 0.0281(6) 0.0010(5) -0.0001(5) -0.0037(6) C6 0.0294(7) 0.0428(8) 0.0346(7) 0.0055(7) 0.0005(5) -0.0100(6) C7 0.0288(7) 0.0517(9) 0.0296(7) 0.0054(7) 0.0064(5) -0.0008(6) C8 0.0327(7) 0.0390(8) 0.0266(6) -0.0017(6) 0.0044(5) 0.0052(6) C9 0.0269(6) 0.0286(7) 0.0260(6) -0.0005(5) 0.0014(5) 0.0000(5) C10 0.0273(6) 0.0225(6) 0.0212(5) -0.0012(4) 0.0056(5) 0.0018(5) C11 0.0322(7) 0.0270(7) 0.0283(6) 0.0024(5) -0.0010(5) -0.0047(5) C12 0.0406(8) 0.0307(7) 0.0292(7) 0.0056(6) -0.0039(6) -0.0006(6) C13 0.0431(8) 0.0223(6) 0.0301(7) 0.0022(5) 0.0090(6) 0.0005(6) C14 0.0317(6) 0.0232(7) 0.0378(7) -0.0043(6) 0.0089(5) -0.0036(5) C15 0.0259(6) 0.0248(6) 0.0313(7) -0.0028(5) 0.0025(5) -0.0001(5) C16 0.0247(6) 0.0260(6) 0.0223(5) 0.0012(5) 0.0021(4) 0.0025(5) C17 0.0244(6) 0.0327(7) 0.0205(6) 0.0000(5) 0.0004(5) -0.0006(5) C18 0.0279(6) 0.0417(8) 0.0250(6) -0.0003(6) 0.0018(5) 0.0042(6) C19 0.0266(7) 0.0554(10) 0.0291(7) -0.0039(7) 0.0060(5) -0.0020(6) C20 0.0346(7) 0.0497(9) 0.0293(7) -0.0002(6) 0.0053(5) -0.0142(7) C21 0.0363(7) 0.0339(7) 0.0274(6) 0.0016(6) 0.0009(5) -0.0068(6) C22 0.0264(6) 0.0306(7) 0.0218(6) -0.0024(5) -0.0017(5) -0.0033(5) C23 0.0277(6) 0.0293(7) 0.0194(5) -0.0018(5) -0.0024(4) 0.0000(5) C24 0.0374(7) 0.0287(7) 0.0247(6) 0.0006(5) -0.0030(5) 0.0038(6) C25 0.0383(7) 0.0349(8) 0.0305(7) 0.0001(6) -0.0009(6) 0.0138(6) C26 0.0314(7) 0.0465(9) 0.0318(7) -0.0002(6) 0.0061(5) 0.0133(6) C27 0.0309(7) 0.0354(7) 0.0273(6) 0.0052(6) 0.0043(5) 0.0049(6) C28 0.0252(6) 0.0281(6) 0.0228(6) -0.0008(5) -0.0007(5) 0.0037(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 C3 1.4269(15) . ? N1 C16 1.4704(16) . ? N1 C2 1.4729(17) . ? N1 C1 1.4837(17) . ? C1 C2 1.4832(17) . ? C2 C3 1.5314(17) . ? C3 C10 1.5255(17) . ? C3 C4 1.5363(16) . ? C4 C5 1.3904(18) . ? C4 C9 1.4000(18) . ? C5 C6 1.3951(19) . ? C6 C7 1.379(2) . ? C7 C8 1.386(2) . ? C8 C9 1.3899(19) . ? C10 C15 1.3931(18) . ? C10 C11 1.3969(19) . ? C11 C12 1.390(2) . ? C12 C13 1.386(2) . ? C13 C14 1.384(2) . ? C14 C15 1.394(2) . ? C16 C28 1.5219(18) . ? C16 C17 1.5239(18) . ? C17 C18 1.3893(19) . ? C17 C22 1.403(2) . ? C18 C19 1.399(2) . ? C19 C20 1.384(3) . ? C20 C21 1.394(2) . ? C21 C22 1.3932(19) . ? C22 C23 1.4732(18) . ? C23 C24 1.3907(19) . ? C23 C28 1.4018(19) . ? C24 C25 1.393(2) . ? C25 C26 1.389(2) . ? C26 C27 1.397(2) . ? C27 C28 1.3902(18) . ? 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 C2 116.75(10) . . ? C16 N1 C1 114.57(10) . . ? C2 N1 C1 60.22(8) . . ? C2 C1 N1 59.53(8) . . ? N1 C2 C1 60.25(8) . . ? N1 C2 C3 114.01(10) . . ? C1 C2 C3 120.85(11) . . ? O1 C3 C10 106.44(9) . . ? O1 C3 C2 108.80(10) . . ? C10 C3 C2 112.14(10) . . ? O1 C3 C4 110.85(10) . . ? C10 C3 C4 110.60(10) . . ? C2 C3 C4 108.03(9) . . ? C5 C4 C9 119.12(12) . . ? C5 C4 C3 121.55(12) . . ? C9 C4 C3 119.28(11) . . ? C4 C5 C6 120.00(13) . . ? C7 C6 C5 120.69(14) . . ? C6 C7 C8 119.65(13) . . ? C7 C8 C9 120.30(14) . . ? C8 C9 C4 120.23(13) . . ? C15 C10 C11 118.97(12) . . ? C15 C10 C3 123.31(11) . . ? C11 C10 C3 117.72(11) . . ? C12 C11 C10 120.50(13) . . ? C13 C12 C11 120.12(13) . . ? C14 C13 C12 119.85(13) . . ? C13 C14 C15 120.28(13) . . ? C10 C15 C14 120.28(12) . . ? N1 C16 C28 111.78(10) . . ? N1 C16 C17 113.21(10) . . ? C28 C16 C17 102.13(11) . . ? C18 C17 C22 120.36(13) . . ? C18 C17 C16 129.42(13) . . ? C22 C17 C16 110.18(11) . . ? C17 C18 C19 118.46(14) . . ? C20 C19 C18 121.17(14) . . ? C19 C20 C21 120.64(14) . . ? C22 C21 C20 118.50(14) . . ? C21 C22 C17 120.84(13) . . ? C21 C22 C23 130.55(13) . . ? C17 C22 C23 108.60(12) . . ? C24 C23 C28 120.94(12) . . ? C24 C23 C22 130.40(13) . . ? C28 C23 C22 108.66(11) . . ? C23 C24 C25 118.40(13) . . ? C26 C25 C24 120.89(13) . . ? C25 C26 C27 120.77(13) . . ? C28 C27 C26 118.63(13) . . ? C27 C28 C23 120.36(12) . . ? C27 C28 C16 129.37(12) . . ? C23 C28 C16 110.27(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N1 C1 C2 107.98(12) . . . . ? C16 N1 C2 C1 -104.36(12) . . . . ? C16 N1 C2 C3 142.56(11) . . . . ? C1 N1 C2 C3 -113.08(12) . . . . ? N1 C1 C2 C3 101.80(13) . . . . ? N1 C2 C3 O1 27.38(14) . . . . ? C1 C2 C3 O1 -41.12(15) . . . . ? N1 C2 C3 C10 144.84(11) . . . . ? C1 C2 C3 C10 76.35(15) . . . . ? N1 C2 C3 C4 -93.03(12) . . . . ? C1 C2 C3 C4 -161.52(12) . . . . ? O1 C3 C4 C5 -10.23(16) . . . . ? C10 C3 C4 C5 -128.05(12) . . . . ? C2 C3 C4 C5 108.88(13) . . . . ? O1 C3 C4 C9 172.27(11) . . . . ? C10 C3 C4 C9 54.45(14) . . . . ? C2 C3 C4 C9 -68.62(14) . . . . ? C9 C4 C5 C6 0.60(19) . . . . ? C3 C4 C5 C6 -176.91(12) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? C5 C6 C7 C8 -0.5(2) . . . . ? C6 C7 C8 C9 -0.1(2) . . . . ? C7 C8 C9 C4 1.0(2) . . . . ? C5 C4 C9 C8 -1.21(19) . . . . ? C3 C4 C9 C8 176.35(12) . . . . ? O1 C3 C10 C15 123.64(13) . . . . ? C2 C3 C10 C15 4.77(16) . . . . ? C4 C3 C10 C15 -115.88(13) . . . . ? O1 C3 C10 C11 -56.42(14) . . . . ? C2 C3 C10 C11 -175.29(11) . . . . ? C4 C3 C10 C11 64.06(14) . . . . ? C15 C10 C11 C12 -0.5(2) . . . . ? C3 C10 C11 C12 179.53(12) . . . . ? C10 C11 C12 C13 -0.3(2) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C11 C10 C15 C14 0.89(19) . . . . ? C3 C10 C15 C14 -179.17(12) . . . . ? C13 C14 C15 C10 -0.42(19) . . . . ? C2 N1 C16 C28 150.39(11) . . . . ? C1 N1 C16 C28 82.79(14) . . . . ? C2 N1 C16 C17 -94.93(13) . . . . ? C1 N1 C16 C17 -162.52(11) . . . . ? N1 C16 C17 C18 58.19(18) . . . . ? C28 C16 C17 C18 178.54(13) . . . . ? N1 C16 C17 C22 -124.39(11) . . . . ? C28 C16 C17 C22 -4.05(13) . . . . ? C22 C17 C18 C19 -0.60(19) . . . . ? C16 C17 C18 C19 176.59(13) . . . . ? C17 C18 C19 C20 -1.1(2) . . . . ? C18 C19 C20 C21 1.5(2) . . . . ? C19 C20 C21 C22 -0.1(2) . . . . ? C20 C21 C22 C17 -1.60(19) . . . . ? C20 C21 C22 C23 179.57(13) . . . . ? C18 C17 C22 C21 1.97(19) . . . . ? C16 C17 C22 C21 -175.71(11) . . . . ? C18 C17 C22 C23 -178.97(11) . . . . ? C16 C17 C22 C23 3.35(14) . . . . ? C21 C22 C23 C24 -2.8(2) . . . . ? C17 C22 C23 C24 178.29(13) . . . . ? C21 C22 C23 C28 177.82(13) . . . . ? C17 C22 C23 C28 -1.12(14) . . . . ? C28 C23 C24 C25 0.60(19) . . . . ? C22 C23 C24 C25 -178.76(13) . . . . ? C23 C24 C25 C26 -0.1(2) . . . . ? C24 C25 C26 C27 -0.6(2) . . . . ? C25 C26 C27 C28 0.7(2) . . . . ? C26 C27 C28 C23 -0.2(2) . . . . ? C26 C27 C28 C16 -179.50(13) . . . . ? C24 C23 C28 C27 -0.46(19) . . . . ? C22 C23 C28 C27 179.02(12) . . . . ? C24 C23 C28 C16 178.96(11) . . . . ? C22 C23 C28 C16 -1.55(14) . . . . ? N1 C16 C28 C27 -55.96(18) . . . . ? C17 C16 C28 C27 -177.30(13) . . . . ? N1 C16 C28 C23 124.68(12) . . . . ? C17 C16 C28 C23 3.35(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 O1 H1 N1 0.84 2.17 2.6680(14) 117.5 . _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.212 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.030 #===END data_2 _database_code_CSD 198145 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O' _chemical_formula_weight 225.28 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2981(6) _cell_length_b 10.1999(9) _cell_length_c 8.6263(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.650(2) _cell_angle_gamma 90.00 _cell_volume 611.91(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4698 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.72 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.934 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details 'SADABS, Sheldrick, G.M.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5345 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 28.71 _reflns_number_total 2768 _reflns_number_gt 2680 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0477P)^2^+0.0836P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom for ArH, free xyz for others' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_number_reflns 2768 _refine_ls_number_parameters 170 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.36492(16) 0.39844(11) 0.48216(14) 0.0300(2) Uani 1 1 d . . . H1A H 0.370(3) 0.329(2) 0.549(2) 0.045 Uiso 1 1 d . . . C1 C 0.27148(18) 0.35367(13) 0.31289(18) 0.0331(3) Uani 1 1 d . . . H1C H 0.195(3) 0.4228(19) 0.241(2) 0.040 Uiso 1 1 d . . . H1D H 0.222(2) 0.264(2) 0.304(2) 0.040 Uiso 1 1 d . . . C2 C 0.48209(15) 0.36780(11) 0.37425(13) 0.0218(2) Uani 1 1 d . . . H2 H 0.549(2) 0.4450(16) 0.3432(18) 0.026 Uiso 1 1 d . . . C3 C 0.61181(15) 0.24751(10) 0.40642(13) 0.0197(2) Uani 1 1 d . . . O1 O 0.51053(12) 0.14826(8) 0.46221(10) 0.02453(18) Uani 1 1 d . . . H1B H 0.571(3) 0.077(2) 0.469(2) 0.037 Uiso 1 1 d . . . C4 C 0.64126(15) 0.21247(11) 0.24280(13) 0.0213(2) Uani 1 1 d . . . C5 C 0.76478(17) 0.28820(13) 0.18304(15) 0.0277(2) Uani 1 1 d . . . H5 H 0.8373 0.3568 0.2477 0.033 Uiso 1 1 calc R . . C6 C 0.7821(2) 0.26353(15) 0.02903(16) 0.0357(3) Uani 1 1 d . . . H6 H 0.8648 0.3162 -0.0114 0.043 Uiso 1 1 calc R . . C7 C 0.6785(2) 0.16209(16) -0.06528(15) 0.0372(3) Uani 1 1 d . . . H7 H 0.6894 0.1456 -0.1705 0.045 Uiso 1 1 calc R . . C8 C 0.5595(2) 0.08538(14) -0.00494(15) 0.0330(3) Uani 1 1 d . . . H8 H 0.4912 0.0145 -0.0681 0.040 Uiso 1 1 calc R . . C9 C 0.53890(16) 0.11094(12) 0.14747(14) 0.0259(2) Uani 1 1 d . . . H9 H 0.4545 0.0588 0.1865 0.031 Uiso 1 1 calc R . . C10 C 0.80523(15) 0.27418(11) 0.53599(13) 0.0213(2) Uani 1 1 d . . . C11 C 0.84870(17) 0.39178(11) 0.62165(14) 0.0247(2) Uani 1 1 d . . . H11 H 0.7581 0.4615 0.5976 0.030 Uiso 1 1 calc R . . C12 C 1.02466(18) 0.40790(12) 0.74265(14) 0.0283(3) Uani 1 1 d . . . H12 H 1.0535 0.4887 0.7996 0.034 Uiso 1 1 calc R . . C13 C 1.15742(18) 0.30655(13) 0.77997(15) 0.0311(3) Uani 1 1 d . . . H13 H 1.2763 0.3171 0.8633 0.037 Uiso 1 1 calc R . . C14 C 1.11501(18) 0.18906(14) 0.69418(16) 0.0322(3) Uani 1 1 d . . . H14 H 1.2055 0.1193 0.7190 0.039 Uiso 1 1 calc R . . C15 C 0.94103(18) 0.17338(12) 0.57249(15) 0.0276(3) Uani 1 1 d . . . H15 H 0.9143 0.0933 0.5136 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0314(5) 0.0227(5) 0.0430(6) -0.0010(4) 0.0219(5) 0.0007(4) C1 0.0218(5) 0.0267(6) 0.0490(7) -0.0021(6) 0.0080(5) 0.0007(5) C2 0.0221(5) 0.0192(5) 0.0254(5) -0.0003(4) 0.0091(4) -0.0002(4) C3 0.0198(5) 0.0180(5) 0.0229(5) -0.0002(4) 0.0088(4) -0.0004(4) O1 0.0257(4) 0.0190(4) 0.0327(4) 0.0018(3) 0.0145(3) -0.0013(3) C4 0.0192(5) 0.0231(5) 0.0212(5) 0.0005(4) 0.0054(4) 0.0038(4) C5 0.0273(5) 0.0300(6) 0.0281(5) -0.0003(5) 0.0117(4) -0.0013(5) C6 0.0380(7) 0.0437(8) 0.0316(6) 0.0048(5) 0.0199(5) 0.0034(6) C7 0.0444(7) 0.0458(8) 0.0215(5) -0.0001(5) 0.0100(5) 0.0141(6) C8 0.0350(6) 0.0343(7) 0.0233(5) -0.0055(5) -0.0006(5) 0.0056(5) C9 0.0243(5) 0.0262(6) 0.0247(5) -0.0001(4) 0.0038(4) 0.0014(4) C10 0.0211(5) 0.0229(5) 0.0212(5) 0.0014(4) 0.0085(4) -0.0013(4) C11 0.0259(5) 0.0228(5) 0.0261(5) -0.0002(4) 0.0089(4) 0.0001(4) C12 0.0313(6) 0.0270(6) 0.0264(5) -0.0034(5) 0.0084(5) -0.0064(5) C13 0.0251(6) 0.0369(7) 0.0274(6) 0.0023(5) 0.0021(5) -0.0041(5) C14 0.0265(6) 0.0290(6) 0.0371(6) 0.0043(5) 0.0036(5) 0.0043(5) C15 0.0262(5) 0.0219(6) 0.0331(6) -0.0017(5) 0.0065(4) 0.0001(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 C2 1.4759(15) . ? N1 C1 1.4839(19) . ? C1 C2 1.4731(16) . ? C2 C3 1.5230(15) . ? C3 O1 1.4208(12) . ? C3 C4 1.5329(14) . ? C3 C10 1.5359(15) . ? C4 C9 1.3908(16) . ? C4 C5 1.3990(16) . ? C5 C6 1.3949(16) . ? C6 C7 1.390(2) . ? C7 C8 1.382(2) . ? C8 C9 1.3926(17) . ? C10 C11 1.3941(16) . ? C10 C15 1.3962(16) . ? C11 C12 1.3974(17) . ? C12 C13 1.3863(18) . ? C13 C14 1.3931(19) . ? C14 C15 1.3898(17) . ? 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 C2 N1 C1 59.70(8) . . ? C2 C1 N1 59.88(8) . . ? C1 C2 N1 60.42(8) . . ? C1 C2 C3 120.66(10) . . ? N1 C2 C3 120.18(10) . . ? O1 C3 C2 106.10(8) . . ? O1 C3 C4 112.23(9) . . ? C2 C3 C4 105.84(8) . . ? O1 C3 C10 109.72(9) . . ? C2 C3 C10 111.92(9) . . ? C4 C3 C10 110.91(8) . . ? C9 C4 C5 118.94(10) . . ? C9 C4 C3 121.19(10) . . ? C5 C4 C3 119.77(10) . . ? C6 C5 C4 120.39(12) . . ? C7 C6 C5 120.11(12) . . ? C8 C7 C6 119.56(12) . . ? C7 C8 C9 120.63(12) . . ? C4 C9 C8 120.35(11) . . ? C11 C10 C15 118.83(10) . . ? C11 C10 C3 123.32(10) . . ? C15 C10 C3 117.81(10) . . ? C10 C11 C12 120.46(11) . . ? C13 C12 C11 120.34(11) . . ? C12 C13 C14 119.41(11) . . ? C15 C14 C13 120.35(12) . . ? C14 C15 C10 120.60(11) . . ? 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 H1B N1 0.84(2) 1.89(2) 2.6990(14) 159.2(17) 2_646 _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.231 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.031 #===END data_4 _database_code_CSD 198146 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35.67 H33.33 N1.33 O1.33' _chemical_formula_weight 501.97 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 rhombohedral _symmetry_space_group_name_H-M R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' _cell_length_a 27.263(2) _cell_length_b 27.263(2) _cell_length_c 9.4764(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6099.7(9) _cell_formula_units_Z 9 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6207 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2406 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS, Sheldrick, G.M.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17684 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.84 _reflns_number_total 6360 _reflns_number_gt 4805 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0667P)^2^+11.2484P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 6360 _refine_ls_number_parameters 335 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.1780 _refine_ls_wR_factor_gt 0.1697 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.44995(11) 0.22528(12) 0.3537(3) 0.0377(6) Uani 1 1 d . . . C1 C 0.42597(16) 0.19873(16) 0.2179(3) 0.0466(8) Uani 1 1 d . . . H1A H 0.4523 0.2075 0.1376 0.056 Uiso 1 1 calc R . . H1B H 0.3882 0.1929 0.1925 0.056 Uiso 1 1 calc R . . C2 C 0.42930(14) 0.16471(13) 0.3357(3) 0.0375(7) Uani 1 1 d . . . H2 H 0.3921 0.1397 0.3828 0.045 Uiso 1 1 calc R . . C3 C 0.47109(14) 0.14317(15) 0.3461(4) 0.0422(8) Uani 1 1 d . . . O1 O 0.48767(12) 0.14494(13) 0.4916(3) 0.0600(7) Uani 1 1 d . . . C4 C 0.4429(2) 0.1094(3) 0.5860(4) 0.0786(15) Uani 1 1 d . . . H4A H 0.4581 0.1134 0.6817 0.118 Uiso 1 1 calc R . . H4B H 0.4260 0.0699 0.5557 0.118 Uiso 1 1 calc R . . H4C H 0.4139 0.1206 0.5853 0.118 Uiso 1 1 calc R . . C5 C 0.52625(16) 0.18044(15) 0.2682(5) 0.0588(11) Uani 1 1 d . . . C6 C 0.52780(19) 0.18052(16) 0.1233(5) 0.0672(13) Uani 1 1 d . . . H6 H 0.4939 0.1579 0.0718 0.081 Uiso 1 1 calc R . . C7 C 0.5788(3) 0.2136(2) 0.0503(8) 0.107(3) Uani 1 1 d . . . H7 H 0.5800 0.2145 -0.0499 0.128 Uiso 1 1 calc R . . C8 C 0.6282(2) 0.24566(17) 0.1317(9) 0.096(2) Uani 1 1 d . . . H8 H 0.6634 0.2685 0.0853 0.115 Uiso 1 1 calc R . . C9 C 0.6266(2) 0.2444(2) 0.2735(10) 0.105(3) Uani 1 1 d . . . H9 H 0.6602 0.2658 0.3267 0.126 Uiso 1 1 calc R . . C10 C 0.57696(16) 0.21252(17) 0.3391(8) 0.0809(17) Uani 1 1 d . . . H10 H 0.5766 0.2119 0.4393 0.097 Uiso 1 1 calc R . . C11 C 0.44547(13) 0.08251(14) 0.2918(3) 0.0379(7) Uani 1 1 d . . . C12 C 0.47460(15) 0.05346(15) 0.3188(3) 0.0436(8) Uani 1 1 d . . . H12 H 0.5100 0.0723 0.3665 0.052 Uiso 1 1 calc R . . C13 C 0.45308(17) -0.00165(16) 0.2780(4) 0.0508(9) Uani 1 1 d . . . H13 H 0.4741 -0.0203 0.2947 0.061 Uiso 1 1 calc R . . C14 C 0.40083(18) -0.03044(16) 0.2124(4) 0.0514(9) Uani 1 1 d . . . H14 H 0.3847 -0.0695 0.1901 0.062 Uiso 1 1 calc R . . C15 C 0.37232(16) -0.00209(16) 0.1795(4) 0.0497(8) Uani 1 1 d . . . H15 H 0.3376 -0.0210 0.1290 0.060 Uiso 1 1 calc R . . C16 C 0.39388(15) 0.05363(15) 0.2196(3) 0.0431(8) Uani 1 1 d . . . H16 H 0.3735 0.0726 0.1980 0.052 Uiso 1 1 calc R . . C17 C 0.41746(13) 0.24629(13) 0.4383(3) 0.0348(6) Uani 1 1 d . . . C18 C 0.44612(14) 0.26334(14) 0.5841(3) 0.0386(7) Uani 1 1 d . . . C19 C 0.4959(2) 0.2629(3) 0.6121(5) 0.0841(16) Uani 1 1 d . . . H19 H 0.5126 0.2511 0.5418 0.101 Uiso 1 1 calc R . . C20 C 0.5210(3) 0.2800(3) 0.7450(6) 0.110(2) Uani 1 1 d . . . H20 H 0.5556 0.2807 0.7629 0.132 Uiso 1 1 calc R . . C21 C 0.4971(2) 0.2959(2) 0.8509(5) 0.0810(15) Uani 1 1 d . . . H21 H 0.5134 0.3049 0.9425 0.097 Uiso 1 1 calc R . . C22 C 0.44981(17) 0.29848(19) 0.8214(4) 0.0591(10) Uani 1 1 d . . . H22 H 0.4340 0.3116 0.8909 0.071 Uiso 1 1 calc R . . C23 C 0.42445(15) 0.28188(16) 0.6896(4) 0.0470(8) Uani 1 1 d . . . H23 H 0.3909 0.2834 0.6715 0.056 Uiso 1 1 calc R . . C24 C 0.42668(13) 0.30085(13) 0.3654(3) 0.0367(7) Uani 1 1 d . . . C25 C 0.47048(16) 0.32974(15) 0.2712(4) 0.0487(8) Uani 1 1 d . . . H25 H 0.4957 0.3161 0.2518 0.058 Uiso 1 1 calc R . . C26 C 0.47840(18) 0.37864(16) 0.2039(4) 0.0583(10) Uani 1 1 d . . . H26 H 0.5086 0.3978 0.1387 0.070 Uiso 1 1 calc R . . C27 C 0.44273(17) 0.39913(15) 0.2315(4) 0.0542(9) Uani 1 1 d . . . H27 H 0.4473 0.4318 0.1840 0.065 Uiso 1 1 calc R . . C28 C 0.39998(17) 0.37168(15) 0.3295(4) 0.0511(9) Uani 1 1 d . . . H28 H 0.3762 0.3867 0.3521 0.061 Uiso 1 1 calc R . . C29 C 0.39130(16) 0.32312(15) 0.3949(4) 0.0473(8) Uani 1 1 d . . . H29 H 0.3612 0.3045 0.4605 0.057 Uiso 1 1 calc R . . C30 C 0.35437(13) 0.20195(13) 0.4502(3) 0.0354(6) Uani 1 1 d . . . C31 C 0.31575(14) 0.19617(16) 0.3469(4) 0.0434(8) Uani 1 1 d . . . H31 H 0.3281 0.2218 0.2696 0.052 Uiso 1 1 calc R . . C32 C 0.25922(15) 0.15351(17) 0.3544(4) 0.0550(10) Uani 1 1 d . . . H32 H 0.2336 0.1500 0.2819 0.066 Uiso 1 1 calc R . . C33 C 0.24045(16) 0.11651(17) 0.4665(5) 0.0586(10) Uani 1 1 d . . . H33 H 0.2018 0.0878 0.4723 0.070 Uiso 1 1 calc R . . C34 C 0.27800(16) 0.12134(15) 0.5705(4) 0.0511(9) Uani 1 1 d . . . H34 H 0.2651 0.0957 0.6477 0.061 Uiso 1 1 calc R . . C35 C 0.33460(15) 0.16357(13) 0.5631(4) 0.0407(7) Uani 1 1 d . . . H35 H 0.3601 0.1664 0.6352 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0345(13) 0.0432(15) 0.0390(14) -0.0024(11) 0.0034(11) 0.0221(12) C1 0.057(2) 0.061(2) 0.0333(16) -0.0041(15) 0.0051(15) 0.0383(19) C2 0.0359(16) 0.0366(16) 0.0356(16) -0.0049(13) 0.0057(13) 0.0147(13) C3 0.0356(17) 0.0448(19) 0.0485(19) -0.0054(15) 0.0034(14) 0.0218(15) O1 0.0507(15) 0.0739(19) 0.0695(18) -0.0221(14) -0.0185(13) 0.0418(15) C4 0.085(3) 0.141(5) 0.041(2) -0.007(3) 0.000(2) 0.080(4) C5 0.043(2) 0.0343(18) 0.101(3) -0.0091(19) 0.019(2) 0.0209(17) C6 0.066(3) 0.0338(19) 0.098(3) 0.005(2) 0.045(2) 0.0216(18) C7 0.116(5) 0.045(3) 0.164(6) 0.029(3) 0.100(5) 0.044(3) C8 0.054(3) 0.0214(19) 0.199(7) 0.002(3) 0.057(4) 0.0087(19) C9 0.055(3) 0.050(3) 0.212(8) -0.021(4) 0.024(4) 0.027(2) C10 0.038(2) 0.037(2) 0.172(5) -0.016(3) 0.002(3) 0.0220(18) C11 0.0355(16) 0.0387(17) 0.0375(16) 0.0030(13) 0.0115(13) 0.0170(14) C12 0.0438(18) 0.0500(19) 0.0427(18) 0.0109(15) 0.0129(14) 0.0278(16) C13 0.060(2) 0.051(2) 0.049(2) 0.0157(17) 0.0178(17) 0.0328(19) C14 0.071(3) 0.0407(18) 0.0405(19) 0.0084(15) 0.0188(18) 0.0260(19) C15 0.051(2) 0.050(2) 0.0415(19) -0.0003(15) 0.0022(16) 0.0211(17) C16 0.0492(19) 0.050(2) 0.0354(16) 0.0058(14) 0.0037(14) 0.0285(17) C17 0.0313(15) 0.0361(16) 0.0347(15) -0.0018(12) -0.0010(12) 0.0152(13) C18 0.0365(16) 0.0390(17) 0.0376(16) -0.0011(13) -0.0012(13) 0.0169(14) C19 0.077(3) 0.123(4) 0.081(3) -0.049(3) -0.037(3) 0.070(3) C20 0.095(4) 0.172(6) 0.101(4) -0.079(4) -0.066(3) 0.095(5) C21 0.079(3) 0.098(4) 0.060(3) -0.027(3) -0.025(2) 0.040(3) C22 0.052(2) 0.070(3) 0.0423(19) -0.0003(18) 0.0080(17) 0.021(2) C23 0.0434(18) 0.057(2) 0.0395(18) -0.0017(16) 0.0046(14) 0.0245(17) C24 0.0368(16) 0.0339(16) 0.0348(16) -0.0036(12) -0.0025(13) 0.0142(14) C25 0.0450(19) 0.0397(18) 0.053(2) 0.0046(15) 0.0072(16) 0.0147(16) C26 0.058(2) 0.043(2) 0.058(2) 0.0102(17) 0.0126(19) 0.0137(18) C27 0.059(2) 0.0389(19) 0.058(2) 0.0032(17) -0.0152(19) 0.0196(18) C28 0.057(2) 0.045(2) 0.058(2) 0.0003(17) -0.0110(18) 0.0311(18) C29 0.052(2) 0.0444(19) 0.0485(19) 0.0033(15) 0.0048(16) 0.0269(17) C30 0.0332(15) 0.0378(16) 0.0377(15) -0.0054(13) 0.0039(12) 0.0196(13) C31 0.0380(17) 0.055(2) 0.0447(18) -0.0037(15) 0.0023(14) 0.0291(16) C32 0.0374(19) 0.063(2) 0.064(2) -0.016(2) -0.0072(17) 0.0247(18) C33 0.0352(19) 0.054(2) 0.070(3) -0.011(2) 0.0106(18) 0.0101(17) C34 0.051(2) 0.044(2) 0.047(2) -0.0033(16) 0.0140(17) 0.0155(17) C35 0.0438(18) 0.0356(16) 0.0423(17) -0.0061(13) 0.0037(14) 0.0196(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 C1 1.460(4) . ? N1 C2 1.464(4) . ? N1 C17 1.504(4) . ? C1 C2 1.483(5) . ? C2 C3 1.523(5) . ? C3 O1 1.444(4) . ? C3 C5 1.520(5) . ? C3 C11 1.527(5) . ? O1 C4 1.431(6) . ? C5 C6 1.374(7) . ? C5 C10 1.385(6) . ? C6 C7 1.404(6) . ? C7 C8 1.414(10) . ? C8 C9 1.344(10) . ? C9 C10 1.340(8) . ? C11 C12 1.397(5) . ? C11 C16 1.399(5) . ? C12 C13 1.368(5) . ? C13 C14 1.383(6) . ? C14 C15 1.378(5) . ? C15 C16 1.380(5) . ? C17 C30 1.534(4) . ? C17 C18 1.541(4) . ? C17 C24 1.543(4) . ? C18 C23 1.379(5) . ? C18 C19 1.388(6) . ? C19 C20 1.397(6) . ? C20 C21 1.379(8) . ? C21 C22 1.354(6) . ? C22 C23 1.389(5) . ? C24 C25 1.379(5) . ? C24 C29 1.401(5) . ? C25 C26 1.394(5) . ? C26 C27 1.367(6) . ? C27 C28 1.382(6) . ? C28 C29 1.371(5) . ? C30 C31 1.388(5) . ? C30 C35 1.402(5) . ? C31 C32 1.393(5) . ? C32 C33 1.376(6) . ? C33 C34 1.379(6) . ? C34 C35 1.391(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 C1 N1 C2 60.9(2) . . ? C1 N1 C17 117.1(3) . . ? C2 N1 C17 121.6(2) . . ? N1 C1 C2 59.7(2) . . ? N1 C2 C1 59.4(2) . . ? N1 C2 C3 119.2(3) . . ? C1 C2 C3 125.5(3) . . ? O1 C3 C5 104.6(3) . . ? O1 C3 C2 109.3(3) . . ? C5 C3 C2 113.1(3) . . ? O1 C3 C11 108.9(3) . . ? C5 C3 C11 108.9(3) . . ? C2 C3 C11 111.7(3) . . ? C4 O1 C3 115.3(3) . . ? C6 C5 C10 117.6(4) . . ? C6 C5 C3 120.4(4) . . ? C10 C5 C3 121.9(5) . . ? C5 C6 C7 120.9(5) . . ? C6 C7 C8 117.4(6) . . ? C9 C8 C7 121.3(5) . . ? C10 C9 C8 119.4(6) . . ? C9 C10 C5 123.3(7) . . ? C12 C11 C16 117.8(3) . . ? C12 C11 C3 118.0(3) . . ? C16 C11 C3 124.1(3) . . ? C13 C12 C11 121.2(3) . . ? C12 C13 C14 120.3(3) . . ? C15 C14 C13 119.5(3) . . ? C14 C15 C16 120.4(4) . . ? C15 C16 C11 120.6(3) . . ? N1 C17 C30 112.4(2) . . ? N1 C17 C18 106.7(2) . . ? C30 C17 C18 111.8(3) . . ? N1 C17 C24 106.6(2) . . ? C30 C17 C24 111.8(3) . . ? C18 C17 C24 107.3(2) . . ? C23 C18 C19 117.7(3) . . ? C23 C18 C17 121.0(3) . . ? C19 C18 C17 121.3(3) . . ? C18 C19 C20 119.1(4) . . ? C21 C20 C19 122.1(5) . . ? C22 C21 C20 118.5(4) . . ? C21 C22 C23 120.0(4) . . ? C18 C23 C22 122.4(3) . . ? C25 C24 C29 118.0(3) . . ? C25 C24 C17 121.2(3) . . ? C29 C24 C17 120.8(3) . . ? C24 C25 C26 121.2(4) . . ? C27 C26 C25 120.1(4) . . ? C26 C27 C28 119.1(3) . . ? C29 C28 C27 121.2(4) . . ? C28 C29 C24 120.3(3) . . ? C31 C30 C35 117.8(3) . . ? C31 C30 C17 121.7(3) . . ? C35 C30 C17 120.4(3) . . ? C30 C31 C32 121.3(4) . . ? C33 C32 C31 120.1(4) . . ? C32 C33 C34 119.7(3) . . ? C33 C34 C35 120.4(4) . . ? C34 C35 C30 120.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 N1 C1 C2 -112.9(3) . . . . ? C17 N1 C2 C1 105.6(3) . . . . ? C1 N1 C2 C3 116.3(3) . . . . ? C17 N1 C2 C3 -138.0(3) . . . . ? N1 C1 C2 C3 -105.9(3) . . . . ? N1 C2 C3 O1 72.5(4) . . . . ? C1 C2 C3 O1 144.0(3) . . . . ? N1 C2 C3 C5 -43.6(4) . . . . ? C1 C2 C3 C5 27.9(5) . . . . ? N1 C2 C3 C11 -166.8(3) . . . . ? C1 C2 C3 C11 -95.4(4) . . . . ? C5 C3 O1 C4 -175.8(3) . . . . ? C2 C3 O1 C4 62.8(4) . . . . ? C11 C3 O1 C4 -59.5(4) . . . . ? O1 C3 C5 C6 168.4(3) . . . . ? C2 C3 C5 C6 -72.8(4) . . . . ? C11 C3 C5 C6 52.0(4) . . . . ? O1 C3 C5 C10 -7.6(4) . . . . ? C2 C3 C5 C10 111.3(4) . . . . ? C11 C3 C5 C10 -123.9(3) . . . . ? C10 C5 C6 C7 -2.2(6) . . . . ? C3 C5 C6 C7 -178.3(3) . . . . ? C5 C6 C7 C8 1.4(6) . . . . ? C6 C7 C8 C9 0.1(7) . . . . ? C7 C8 C9 C10 -0.6(8) . . . . ? C8 C9 C10 C5 -0.3(7) . . . . ? C6 C5 C10 C9 1.8(6) . . . . ? C3 C5 C10 C9 177.8(4) . . . . ? O1 C3 C11 C12 -47.4(4) . . . . ? C5 C3 C11 C12 66.2(4) . . . . ? C2 C3 C11 C12 -168.2(3) . . . . ? O1 C3 C11 C16 130.9(3) . . . . ? C5 C3 C11 C16 -115.5(4) . . . . ? C2 C3 C11 C16 10.1(4) . . . . ? C16 C11 C12 C13 -0.9(5) . . . . ? C3 C11 C12 C13 177.5(3) . . . . ? C11 C12 C13 C14 -2.0(5) . . . . ? C12 C13 C14 C15 4.5(5) . . . . ? C13 C14 C15 C16 -4.1(5) . . . . ? C14 C15 C16 C11 1.2(5) . . . . ? C12 C11 C16 C15 1.3(5) . . . . ? C3 C11 C16 C15 -177.0(3) . . . . ? C1 N1 C17 C30 48.4(4) . . . . ? C2 N1 C17 C30 -22.6(4) . . . . ? C1 N1 C17 C18 171.2(3) . . . . ? C2 N1 C17 C18 100.3(3) . . . . ? C1 N1 C17 C24 -74.4(3) . . . . ? C2 N1 C17 C24 -145.4(3) . . . . ? N1 C17 C18 C23 -176.8(3) . . . . ? C30 C17 C18 C23 -53.5(4) . . . . ? C24 C17 C18 C23 69.3(4) . . . . ? N1 C17 C18 C19 6.0(5) . . . . ? C30 C17 C18 C19 129.2(4) . . . . ? C24 C17 C18 C19 -107.9(4) . . . . ? C23 C18 C19 C20 1.2(8) . . . . ? C17 C18 C19 C20 178.5(5) . . . . ? C18 C19 C20 C21 1.8(11) . . . . ? C19 C20 C21 C22 -4.4(10) . . . . ? C20 C21 C22 C23 4.0(8) . . . . ? C19 C18 C23 C22 -1.5(6) . . . . ? C17 C18 C23 C22 -178.9(3) . . . . ? C21 C22 C23 C18 -1.1(6) . . . . ? N1 C17 C24 C25 -17.6(4) . . . . ? C30 C17 C24 C25 -140.7(3) . . . . ? C18 C17 C24 C25 96.4(3) . . . . ? N1 C17 C24 C29 163.6(3) . . . . ? C30 C17 C24 C29 40.4(4) . . . . ? C18 C17 C24 C29 -82.5(3) . . . . ? C29 C24 C25 C26 -1.9(5) . . . . ? C17 C24 C25 C26 179.2(3) . . . . ? C24 C25 C26 C27 0.5(6) . . . . ? C25 C26 C27 C28 1.8(6) . . . . ? C26 C27 C28 C29 -2.7(6) . . . . ? C27 C28 C29 C24 1.3(6) . . . . ? C25 C24 C29 C28 1.0(5) . . . . ? C17 C24 C29 C28 179.9(3) . . . . ? N1 C17 C30 C31 -85.5(4) . . . . ? C18 C17 C30 C31 154.6(3) . . . . ? C24 C17 C30 C31 34.3(4) . . . . ? N1 C17 C30 C35 90.7(3) . . . . ? C18 C17 C30 C35 -29.2(4) . . . . ? C24 C17 C30 C35 -149.5(3) . . . . ? C35 C30 C31 C32 -0.3(5) . . . . ? C17 C30 C31 C32 176.0(3) . . . . ? C30 C31 C32 C33 0.9(5) . . . . ? C31 C32 C33 C34 -0.9(6) . . . . ? C32 C33 C34 C35 0.4(6) . . . . ? C33 C34 C35 C30 0.2(5) . . . . ? C31 C30 C35 C34 -0.2(5) . . . . ? C17 C30 C35 C34 -176.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.304 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.049 #===END