# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/430 data_wm267 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H35 N3 O6' _chemical_formula_weight 461.55 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 22.179(2) _cell_length_b 10.9087(8) _cell_length_c 10.7255(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.857(11) _cell_angle_gamma 90.00 _cell_volume 2519.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8872 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Stoe IPDS' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9154 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 26.04 _reflns_number_total 4539 _reflns_number_gt 3461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1997)' _computing_cell_refinement 'IPDS (Stoe, 1997)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSTEP (Stoe, 1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0391P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(9) _refine_ls_number_reflns 4539 _refine_ls_number_parameters 300 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _refine_ls_shift/su_max 0.002 _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 0.92643(6) 0.61286(14) 1.00581(14) 0.0400(4) Uani 1 1 d . . . O2 O 1.02442(7) 0.30480(16) 0.97004(17) 0.0485(4) Uani 1 1 d . . . O3 O 0.92316(8) 0.2900(2) 0.9564(2) 0.0696(6) Uani 1 1 d . . . O4 O 0.78050(6) 0.55351(12) 1.12787(14) 0.0325(3) Uani 1 1 d . . . O5 O 0.62862(6) 0.60761(15) 0.66414(14) 0.0404(4) Uani 1 1 d . . . O6 O 0.63746(7) 0.62191(16) 0.88112(16) 0.0433(4) Uani 1 1 d . . . N1 N 0.79813(7) 0.67438(14) 0.96809(16) 0.0240(3) Uani 1 1 d . . . N2 N 0.90099(7) 0.50877(17) 0.81958(18) 0.0360(4) Uani 1 1 d . . . H2N H 0.8718 0.4912 0.7505 0.035(6) Uiso 1 1 calc R . . N3 N 0.70507(7) 0.51209(15) 0.79749(17) 0.0304(4) Uani 1 1 d . . . H3N H 0.7151 0.4886 0.7266 0.034(6) Uiso 1 1 calc R . . C1 C 0.82726(8) 0.65900(17) 0.85911(19) 0.0260(4) Uani 1 1 d . . . H1 H 0.7992 0.6058 0.7943 0.031 Uiso 1 1 calc R . . C2 C 0.83415(9) 0.78267(19) 0.7926(2) 0.0311(5) Uani 1 1 d . . . C3 C 0.87037(11) 0.7650(2) 0.6894(2) 0.0426(6) Uani 1 1 d . . . H3A H 0.8481 0.7073 0.6244 0.064 Uiso 1 1 calc R . . H3B H 0.9117 0.7322 0.7288 0.064 Uiso 1 1 calc R . . H3C H 0.8746 0.8440 0.6488 0.064 Uiso 1 1 calc R . . C4 C 0.76845(10) 0.8284(2) 0.7291(2) 0.0374(5) Uani 1 1 d . . . H4A H 0.7448 0.8390 0.7948 0.056 Uiso 1 1 calc R . . H4B H 0.7475 0.7683 0.6655 0.056 Uiso 1 1 calc R . . H4C H 0.7711 0.9071 0.6867 0.056 Uiso 1 1 calc R . . C5 C 0.86925(10) 0.87223(19) 0.8941(2) 0.0364(5) Uani 1 1 d . . . H5A H 0.9117 0.8407 0.9302 0.044 Uiso 1 1 calc R . . H5B H 0.8730 0.9523 0.8532 0.044 Uiso 1 1 calc R . . C6 C 0.83639(10) 0.89006(19) 1.0021(2) 0.0355(5) Uani 1 1 d . . . H6A H 0.7972 0.9350 0.9676 0.043 Uiso 1 1 calc R . . H6B H 0.8628 0.9423 1.0689 0.043 Uiso 1 1 calc R . . C7 C 0.82115(8) 0.77160(18) 1.06608(18) 0.0274(5) Uani 1 1 d . . . H7 H 0.8597 0.7416 1.1274 0.033 Uiso 1 1 calc R . . C8 C 0.77310(10) 0.80353(18) 1.1409(2) 0.0300(5) Uani 1 1 d . . . C9 C 0.71274(10) 0.8355(2) 1.0772(2) 0.0401(6) Uani 1 1 d . . . H9 H 0.7005 0.8312 0.9862 0.048 Uiso 1 1 calc R . . C10 C 0.67043(11) 0.8737(2) 1.1455(3) 0.0510(7) Uani 1 1 d . . . H10 H 0.6295 0.8957 1.1008 0.061 Uiso 1 1 calc R . . C11 C 0.68727(12) 0.8799(2) 1.2782(3) 0.0529(7) Uani 1 1 d . . . H11 H 0.6582 0.9060 1.3248 0.063 Uiso 1 1 calc R . . C12 C 0.74673(13) 0.8478(2) 1.3416(3) 0.0469(6) Uani 1 1 d . . . H12 H 0.7586 0.8512 1.4327 0.056 Uiso 1 1 calc R . . C13 C 0.78970(11) 0.81051(19) 1.2736(2) 0.0376(5) Uani 1 1 d . . . H13 H 0.8307 0.7897 1.3186 0.045 Uiso 1 1 calc R . . C14 C 0.88924(8) 0.59150(19) 0.9031(2) 0.0287(5) Uani 1 1 d . . . C15 C 0.96022(9) 0.4480(2) 0.8402(2) 0.0361(5) Uani 1 1 d . . . H15A H 0.9935 0.5075 0.8765 0.043 Uiso 1 1 calc R . . H15B H 0.9665 0.4199 0.7565 0.043 Uiso 1 1 calc R . . C16 C 0.96579(9) 0.3398(2) 0.9293(2) 0.0354(5) Uani 1 1 d . . . C17 C 1.03509(13) 0.1943(3) 1.0478(3) 0.0617(8) Uani 1 1 d . . . H17A H 1.0797 0.1766 1.0725 0.093 Uiso 1 1 calc R . . H17B H 1.0132 0.1254 0.9982 0.093 Uiso 1 1 calc R . . H17C H 1.0196 0.2063 1.1252 0.093 Uiso 1 1 calc R . . C18 C 0.77560(8) 0.57109(17) 1.0122(2) 0.0252(4) Uani 1 1 d . . . C19 C 0.74270(9) 0.47286(18) 0.9195(2) 0.0317(5) Uani 1 1 d . . . H19A H 0.7747 0.4161 0.9027 0.038 Uiso 1 1 calc R . . H19B H 0.7159 0.4251 0.9635 0.038 Uiso 1 1 calc R . . C20 C 0.65476(9) 0.58407(19) 0.7890(2) 0.0331(5) Uani 1 1 d . . . C21 C 0.57407(10) 0.6882(2) 0.6267(2) 0.0407(5) Uani 1 1 d . . . C22 C 0.56208(12) 0.6863(3) 0.4812(3) 0.0587(7) Uani 1 1 d . . . H22A H 0.5981 0.7203 0.4552 0.088 Uiso 1 1 calc R . . H22B H 0.5252 0.7357 0.4441 0.088 Uiso 1 1 calc R . . H22C H 0.5552 0.6017 0.4504 0.088 Uiso 1 1 calc R . . C23 C 0.51963(10) 0.6369(2) 0.6717(3) 0.0475(6) Uani 1 1 d . . . H23A H 0.5290 0.6387 0.7658 0.071 Uiso 1 1 calc R . . H23B H 0.5120 0.5521 0.6419 0.071 Uiso 1 1 calc R . . H23C H 0.4826 0.6866 0.6368 0.071 Uiso 1 1 calc R . . C24 C 0.59045(11) 0.8169(2) 0.6782(3) 0.0547(7) Uani 1 1 d . . . H24A H 0.5981 0.8162 0.7721 0.082 Uiso 1 1 calc R . . H24B H 0.5559 0.8725 0.6425 0.082 Uiso 1 1 calc R . . H24C H 0.6279 0.8450 0.6532 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0324(7) 0.0449(9) 0.0358(10) -0.0096(7) -0.0053(7) 0.0067(7) O2 0.0314(8) 0.0481(10) 0.0655(12) 0.0167(8) 0.0109(7) 0.0091(7) O3 0.0387(9) 0.0932(16) 0.0769(16) 0.0343(12) 0.0137(9) -0.0049(9) O4 0.0406(8) 0.0326(8) 0.0234(10) 0.0058(6) 0.0059(6) 0.0027(6) O5 0.0359(8) 0.0503(10) 0.0309(10) -0.0031(7) 0.0003(6) 0.0132(7) O6 0.0401(8) 0.0547(10) 0.0362(11) -0.0086(8) 0.0113(7) 0.0088(7) N1 0.0288(8) 0.0221(8) 0.0207(9) -0.0004(7) 0.0051(6) 0.0007(7) N2 0.0313(9) 0.0400(10) 0.0328(11) -0.0084(8) 0.0001(8) 0.0087(8) N3 0.0312(9) 0.0340(9) 0.0249(11) -0.0059(7) 0.0045(7) 0.0022(7) C1 0.0280(9) 0.0274(10) 0.0214(11) 0.0004(8) 0.0040(8) 0.0013(8) C2 0.0321(10) 0.0304(11) 0.0308(13) 0.0061(9) 0.0077(9) 0.0013(8) C3 0.0489(13) 0.0429(13) 0.0409(16) 0.0087(10) 0.0204(11) -0.0003(11) C4 0.0399(12) 0.0374(13) 0.0325(14) 0.0088(10) 0.0040(9) 0.0071(10) C5 0.0385(12) 0.0281(11) 0.0419(15) 0.0027(10) 0.0085(10) -0.0038(9) C6 0.0419(11) 0.0256(11) 0.0373(14) -0.0004(9) 0.0057(10) -0.0034(9) C7 0.0327(10) 0.0247(10) 0.0225(12) -0.0026(8) 0.0022(8) 0.0011(8) C8 0.0384(11) 0.0244(10) 0.0267(13) -0.0041(8) 0.0068(8) -0.0011(8) C9 0.0388(12) 0.0418(13) 0.0377(15) -0.0101(10) 0.0052(10) 0.0044(10) C10 0.0443(14) 0.0477(15) 0.063(2) -0.0144(13) 0.0173(12) -0.0003(11) C11 0.0621(17) 0.0373(13) 0.072(2) -0.0127(13) 0.0407(15) -0.0044(12) C12 0.0819(18) 0.0297(12) 0.0350(15) -0.0041(10) 0.0260(12) -0.0054(11) C13 0.0546(14) 0.0252(11) 0.0309(14) -0.0012(9) 0.0060(10) 0.0002(9) C14 0.0274(10) 0.0299(11) 0.0282(13) -0.0015(8) 0.0053(9) -0.0003(8) C15 0.0325(11) 0.0379(12) 0.0407(15) -0.0017(10) 0.0140(9) 0.0077(9) C16 0.0317(11) 0.0426(13) 0.0332(14) -0.0046(9) 0.0103(9) 0.0011(9) C17 0.0598(16) 0.0548(17) 0.072(2) 0.0266(15) 0.0182(14) 0.0169(13) C18 0.0251(9) 0.0243(10) 0.0254(13) 0.0031(8) 0.0045(7) 0.0053(8) C19 0.0372(10) 0.0255(10) 0.0309(13) 0.0003(9) 0.0051(9) -0.0023(8) C20 0.0305(10) 0.0342(11) 0.0335(14) -0.0032(9) 0.0056(9) 0.0007(8) C21 0.0311(11) 0.0419(13) 0.0438(15) -0.0012(11) -0.0012(9) 0.0085(9) C22 0.0487(14) 0.076(2) 0.0447(18) 0.0108(14) -0.0012(11) 0.0098(13) C23 0.0378(12) 0.0491(14) 0.0512(17) -0.0036(11) 0.0021(11) -0.0012(10) C24 0.0437(13) 0.0385(14) 0.077(2) -0.0016(13) 0.0046(12) 0.0042(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.230(2) . ? O2 C16 1.325(2) . ? O2 C17 1.453(3) . ? O3 C16 1.186(3) . ? O4 C18 1.234(2) . ? O5 C20 1.350(3) . ? O5 C21 1.471(3) . ? O6 C20 1.215(3) . ? N1 C18 1.363(3) . ? N1 C1 1.474(3) . ? N1 C7 1.494(2) . ? N2 C14 1.340(3) . ? N2 C15 1.441(2) . ? N3 C20 1.350(3) . ? N3 C19 1.438(3) . ? C1 C14 1.531(3) . ? C1 C2 1.551(3) . ? C2 C3 1.528(3) . ? C2 C5 1.530(3) . ? C2 C4 1.536(3) . ? C5 C6 1.522(3) . ? C6 C7 1.538(3) . ? C7 C8 1.520(3) . ? C8 C13 1.384(3) . ? C8 C9 1.394(3) . ? C9 C10 1.385(3) . ? C10 C11 1.384(4) . ? C11 C12 1.377(4) . ? C12 C13 1.393(3) . ? C15 C16 1.505(3) . ? C18 C19 1.524(3) . ? C21 C23 1.511(4) . ? C21 C22 1.519(4) . ? C21 C24 1.521(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 C16 O2 C17 116.13(19) . . ? C20 O5 C21 120.94(17) . . ? C18 N1 C1 116.63(15) . . ? C18 N1 C7 115.75(17) . . ? C1 N1 C7 119.83(15) . . ? C14 N2 C15 121.55(17) . . ? C20 N3 C19 121.66(18) . . ? N1 C1 C14 110.00(15) . . ? N1 C1 C2 112.09(15) . . ? C14 C1 C2 112.35(15) . . ? C3 C2 C5 109.27(18) . . ? C3 C2 C4 109.14(18) . . ? C5 C2 C4 112.01(17) . . ? C3 C2 C1 110.50(17) . . ? C5 C2 C1 108.51(17) . . ? C4 C2 C1 107.39(16) . . ? C6 C5 C2 111.63(17) . . ? C5 C6 C7 115.38(17) . . ? N1 C7 C8 111.67(15) . . ? N1 C7 C6 110.93(16) . . ? C8 C7 C6 107.44(17) . . ? C13 C8 C9 118.6(2) . . ? C13 C8 C7 120.53(19) . . ? C9 C8 C7 120.71(19) . . ? C10 C9 C8 120.6(2) . . ? C11 C10 C9 120.5(2) . . ? C12 C11 C10 119.1(2) . . ? C11 C12 C13 120.7(3) . . ? C8 C13 C12 120.5(2) . . ? O1 C14 N2 122.02(18) . . ? O1 C14 C1 123.02(18) . . ? N2 C14 C1 114.94(16) . . ? N2 C15 C16 113.07(18) . . ? O3 C16 O2 124.4(2) . . ? O3 C16 C15 124.5(2) . . ? O2 C16 C15 111.11(18) . . ? O4 C18 N1 121.77(18) . . ? O4 C18 C19 117.40(17) . . ? N1 C18 C19 120.83(19) . . ? N3 C19 C18 117.87(16) . . ? O6 C20 N3 124.06(19) . . ? O6 C20 O5 126.72(18) . . ? N3 C20 O5 109.22(18) . . ? O5 C21 C23 111.1(2) . . ? O5 C21 C22 101.70(19) . . ? C23 C21 C22 111.5(2) . . ? O5 C21 C24 110.06(17) . . ? C23 C21 C24 111.4(2) . . ? C22 C21 C24 110.7(2) . . ? 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 C18 N1 C1 C14 -70.4(2) . . . . ? C7 N1 C1 C14 77.5(2) . . . . ? C18 N1 C1 C2 163.81(16) . . . . ? C7 N1 C1 C2 -48.2(2) . . . . ? N1 C1 C2 C3 174.21(16) . . . . ? C14 C1 C2 C3 49.7(2) . . . . ? N1 C1 C2 C5 54.4(2) . . . . ? C14 C1 C2 C5 -70.1(2) . . . . ? N1 C1 C2 C4 -66.9(2) . . . . ? C14 C1 C2 C4 168.68(17) . . . . ? C3 C2 C5 C6 -178.02(17) . . . . ? C4 C2 C5 C6 60.9(2) . . . . ? C1 C2 C5 C6 -57.5(2) . . . . ? C2 C5 C6 C7 53.0(2) . . . . ? C18 N1 C7 C8 -51.9(2) . . . . ? C1 N1 C7 C8 159.84(16) . . . . ? C18 N1 C7 C6 -171.74(16) . . . . ? C1 N1 C7 C6 40.0(2) . . . . ? C5 C6 C7 N1 -41.3(2) . . . . ? C5 C6 C7 C8 -163.61(17) . . . . ? N1 C7 C8 C13 132.09(19) . . . . ? C6 C7 C8 C13 -106.1(2) . . . . ? N1 C7 C8 C9 -52.9(2) . . . . ? C6 C7 C8 C9 69.0(2) . . . . ? C13 C8 C9 C10 0.1(3) . . . . ? C7 C8 C9 C10 -175.0(2) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C9 C8 C13 C12 0.5(3) . . . . ? C7 C8 C13 C12 175.6(2) . . . . ? C11 C12 C13 C8 -0.8(3) . . . . ? C15 N2 C14 O1 -5.6(3) . . . . ? C15 N2 C14 C1 172.78(18) . . . . ? N1 C1 C14 O1 -41.4(3) . . . . ? C2 C1 C14 O1 84.2(2) . . . . ? N1 C1 C14 N2 140.18(17) . . . . ? C2 C1 C14 N2 -94.2(2) . . . . ? C14 N2 C15 C16 82.5(3) . . . . ? C17 O2 C16 O3 3.1(4) . . . . ? C17 O2 C16 C15 -174.8(2) . . . . ? N2 C15 C16 O3 17.1(3) . . . . ? N2 C15 C16 O2 -165.00(18) . . . . ? C1 N1 C18 O4 141.34(17) . . . . ? C7 N1 C18 O4 -7.9(2) . . . . ? C1 N1 C18 C19 -39.2(2) . . . . ? C7 N1 C18 C19 171.55(16) . . . . ? C20 N3 C19 C18 -62.1(3) . . . . ? O4 C18 C19 N3 144.35(18) . . . . ? N1 C18 C19 N3 -35.2(3) . . . . ? C19 N3 C20 O6 0.5(3) . . . . ? C19 N3 C20 O5 179.46(17) . . . . ? C21 O5 C20 O6 1.2(3) . . . . ? C21 O5 C20 N3 -177.68(17) . . . . ? C20 O5 C21 C23 -61.1(3) . . . . ? C20 O5 C21 C22 -179.9(2) . . . . ? C20 O5 C21 C24 62.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.116 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.035 data_wm1951 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 N O3' _chemical_formula_weight 261.31 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.1046(7) _cell_length_b 7.2949(5) _cell_length_c 13.3142(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.036(12) _cell_angle_gamma 90.00 _cell_volume 689.07(11) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description quader _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.62 _exptl_crystal_size_min 0.51 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9254 _exptl_absorpt_correction_T_max 0.9567 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Stoe IPDS' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5346 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.97 _reflns_number_total 2511 _reflns_number_gt 2330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1997)' _computing_cell_refinement 'IPDS (Stoe, 1997)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSTEP (Stoe, 1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0574P)^2^+0.0315P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(10) _refine_ls_number_reflns 2511 _refine_ls_number_parameters 242 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.039 _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 1.63808(15) 0.33249(19) 0.73344(10) 0.0454(3) Uani 1 1 d . . . H1O H 1.750(3) 0.300(4) 0.7191(15) 0.049(6) Uiso 1 1 d . . . O2 O 1.69149(16) 0.5639(2) 0.63101(11) 0.0531(4) Uani 1 1 d . . . O3 O 0.99789(12) 0.23962(15) 0.72461(8) 0.0331(3) Uani 1 1 d . . . N1 N 1.25950(14) 0.39860(17) 0.69000(8) 0.0220(3) Uani 1 1 d . . . C1 C 1.39233(17) 0.5495(2) 0.71357(10) 0.0225(3) Uani 1 1 d . . . H1 H 1.398(2) 0.563(3) 0.7887(13) 0.029(4) Uiso 1 1 d . . . C2 C 1.31697(18) 0.7283(2) 0.66310(11) 0.0279(3) Uani 1 1 d . . . C3 C 1.2789(2) 0.6963(3) 0.54930(11) 0.0332(4) Uani 1 1 d . . . H3A H 1.231(3) 0.817(4) 0.5211(17) 0.057(6) Uiso 1 1 d . . . H3B H 1.396(3) 0.676(3) 0.5178(13) 0.033(4) Uiso 1 1 d . . . C4 C 1.1534(2) 0.5304(3) 0.52662(11) 0.0340(4) Uani 1 1 d . . . H4A H 1.021(3) 0.548(3) 0.5482(14) 0.037(5) Uiso 1 1 d . . . H4B H 1.153(3) 0.504(3) 0.4521(15) 0.038(5) Uiso 1 1 d . . . C5 C 1.23046(19) 0.3611(2) 0.58148(10) 0.0286(3) Uani 1 1 d . . . H5A H 1.147(2) 0.259(3) 0.5761(13) 0.033(4) Uiso 1 1 d . . . H5B H 1.354(2) 0.336(3) 0.5559(13) 0.030(4) Uiso 1 1 d . . . C6 C 1.59093(18) 0.4871(2) 0.68644(11) 0.0275(3) Uani 1 1 d . . . C7 C 1.4555(3) 0.8877(3) 0.68110(16) 0.0428(4) Uani 1 1 d . . . H7A H 1.566(4) 0.870(4) 0.6496(19) 0.064 Uiso 1 1 d . . . H7B H 1.478(3) 0.912(4) 0.748(2) 0.064 Uiso 1 1 d . . . H7C H 1.394(4) 0.995(4) 0.655(2) 0.064 Uiso 1 1 d . . . C8 C 1.1339(2) 0.7803(2) 0.71273(13) 0.0371(4) Uani 1 1 d . . . H8A H 1.031(3) 0.686(4) 0.7019(17) 0.056 Uiso 1 1 d . . . H8B H 1.091(3) 0.900(4) 0.6856(17) 0.056 Uiso 1 1 d . . . H8C H 1.154(3) 0.793(4) 0.7852(17) 0.056 Uiso 1 1 d . . . C9 C 1.13684(16) 0.3321(2) 0.75417(10) 0.0235(3) Uani 1 1 d . . . C10 C 1.17170(19) 0.3660(2) 0.86476(11) 0.0292(3) Uani 1 1 d . . . C11 C 1.0271(3) 0.4412(2) 0.91827(13) 0.0393(4) Uani 1 1 d . . . H11 H 0.907(3) 0.476(3) 0.8815(14) 0.035(5) Uiso 1 1 d . . . C12 C 1.0503(3) 0.4647(3) 1.02165(14) 0.0519(5) Uani 1 1 d . . . H12 H 0.944(3) 0.513(4) 1.0636(17) 0.054(6) Uiso 1 1 d . . . C13 C 1.2149(3) 0.4105(4) 1.07193(15) 0.0605(6) Uani 1 1 d . . . H13 H 1.235(4) 0.418(5) 1.143(2) 0.080(8) Uiso 1 1 d . . . C14 C 1.3585(3) 0.3318(4) 1.02009(14) 0.0585(6) Uani 1 1 d . . . H14 H 1.475(3) 0.272(4) 1.0560(18) 0.062(7) Uiso 1 1 d . . . C15 C 1.3377(2) 0.3102(3) 0.91591(13) 0.0410(4) Uani 1 1 d . . . H15 H 1.435(3) 0.259(3) 0.8782(15) 0.051(6) 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 0.0217(5) 0.0453(8) 0.0702(8) 0.0188(6) 0.0113(5) 0.0094(5) O2 0.0325(6) 0.0594(9) 0.0691(9) 0.0212(7) 0.0184(5) 0.0033(6) O3 0.0188(4) 0.0278(6) 0.0529(7) -0.0015(5) 0.0043(4) -0.0028(4) N1 0.0186(5) 0.0225(6) 0.0249(5) -0.0014(4) -0.0003(4) -0.0013(4) C1 0.0200(6) 0.0226(7) 0.0247(6) 0.0000(5) -0.0009(5) -0.0022(5) C2 0.0280(7) 0.0245(8) 0.0312(7) 0.0043(6) -0.0001(5) -0.0016(6) C3 0.0324(8) 0.0371(10) 0.0302(7) 0.0108(6) 0.0020(6) 0.0004(6) C4 0.0283(7) 0.0477(11) 0.0254(7) 0.0001(6) -0.0044(5) -0.0015(6) C5 0.0251(6) 0.0335(9) 0.0270(7) -0.0078(6) 0.0002(5) -0.0012(6) C6 0.0192(6) 0.0299(8) 0.0333(7) -0.0003(6) -0.0006(5) -0.0029(5) C7 0.0483(9) 0.0287(10) 0.0510(11) 0.0047(7) -0.0020(8) -0.0089(8) C8 0.0391(8) 0.0303(11) 0.0419(9) -0.0002(7) 0.0028(6) 0.0105(7) C9 0.0185(6) 0.0174(7) 0.0347(7) 0.0013(5) 0.0026(5) 0.0048(5) C10 0.0310(7) 0.0256(9) 0.0317(7) 0.0052(6) 0.0069(5) -0.0007(6) C11 0.0434(9) 0.0348(10) 0.0406(9) 0.0019(7) 0.0123(7) 0.0082(7) C12 0.0706(13) 0.0450(12) 0.0422(10) -0.0030(8) 0.0219(9) 0.0045(10) C13 0.0786(14) 0.0726(16) 0.0310(9) 0.0019(9) 0.0084(9) -0.0091(12) C14 0.0550(10) 0.0828(17) 0.0371(9) 0.0151(10) -0.0042(8) -0.0010(11) C15 0.0354(8) 0.0531(11) 0.0347(8) 0.0111(7) 0.0046(6) 0.0045(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 C6 1.324(2) . ? O1 H1O 0.86(2) . ? O2 C6 1.193(2) . ? O3 C9 1.2423(17) . ? N1 C9 1.3430(18) . ? N1 C1 1.4728(17) . ? N1 C5 1.4743(17) . ? C1 C6 1.5434(18) . ? C1 C2 1.550(2) . ? C1 H1 1.004(18) . ? C2 C7 1.534(2) . ? C2 C8 1.537(2) . ? C2 C3 1.543(2) . ? C3 C4 1.523(2) . ? C3 H3A 1.01(3) . ? C3 H3B 0.96(2) . ? C4 C5 1.522(2) . ? C4 H4A 1.01(2) . ? C4 H4B 1.01(2) . ? C5 H5A 0.95(2) . ? C5 H5B 0.978(17) . ? C7 H7A 0.92(3) . ? C7 H7B 0.91(3) . ? C7 H7C 0.96(3) . ? C8 H8A 1.01(3) . ? C8 H8B 0.98(3) . ? C8 H8C 0.97(2) . ? C9 C10 1.501(2) . ? C10 C15 1.391(2) . ? C10 C11 1.393(2) . ? C11 C12 1.388(3) . ? C11 H11 0.99(2) . ? C12 C13 1.374(3) . ? C12 H12 1.02(2) . ? C13 C14 1.386(3) . ? C13 H13 0.96(3) . ? C14 C15 1.396(3) . ? C14 H14 1.03(2) . ? C15 H15 0.95(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 C6 O1 H1O 110.3(16) . . ? C9 N1 C1 124.36(11) . . ? C9 N1 C5 119.65(11) . . ? C1 N1 C5 113.73(11) . . ? N1 C1 C6 108.27(12) . . ? N1 C1 C2 109.51(10) . . ? C6 C1 C2 116.46(11) . . ? N1 C1 H1 106.1(11) . . ? C6 C1 H1 105.9(10) . . ? C2 C1 H1 110.1(11) . . ? C7 C2 C8 107.24(14) . . ? C7 C2 C3 110.26(13) . . ? C8 C2 C3 110.55(12) . . ? C7 C2 C1 111.48(12) . . ? C8 C2 C1 107.57(11) . . ? C3 C2 C1 109.68(13) . . ? C4 C3 C2 112.67(12) . . ? C4 C3 H3A 115.9(14) . . ? C2 C3 H3A 105.7(13) . . ? C4 C3 H3B 107.7(13) . . ? C2 C3 H3B 109.9(10) . . ? H3A C3 H3B 104.6(18) . . ? C5 C4 C3 110.96(11) . . ? C5 C4 H4A 106.4(13) . . ? C3 C4 H4A 113.0(13) . . ? C5 C4 H4B 107.6(12) . . ? C3 C4 H4B 108.4(12) . . ? H4A C4 H4B 110.3(14) . . ? N1 C5 C4 110.35(12) . . ? N1 C5 H5A 105.8(10) . . ? C4 C5 H5A 112.9(11) . . ? N1 C5 H5B 107.1(10) . . ? C4 C5 H5B 107.1(12) . . ? H5A C5 H5B 113.4(16) . . ? O2 C6 O1 123.17(14) . . ? O2 C6 C1 126.24(15) . . ? O1 C6 C1 110.60(12) . . ? C2 C7 H7A 112.2(18) . . ? C2 C7 H7B 112.1(17) . . ? H7A C7 H7B 111(2) . . ? C2 C7 H7C 106.7(16) . . ? H7A C7 H7C 109(2) . . ? H7B C7 H7C 105(2) . . ? C2 C8 H8A 113.1(14) . . ? C2 C8 H8B 108.3(13) . . ? H8A C8 H8B 110.1(19) . . ? C2 C8 H8C 111.3(13) . . ? H8A C8 H8C 106(2) . . ? H8B C8 H8C 108(2) . . ? O3 C9 N1 121.75(12) . . ? O3 C9 C10 119.17(12) . . ? N1 C9 C10 119.06(12) . . ? C15 C10 C11 119.59(14) . . ? C15 C10 C9 121.58(13) . . ? C11 C10 C9 118.60(13) . . ? C12 C11 C10 120.22(16) . . ? C12 C11 H11 120.7(11) . . ? C10 C11 H11 119.0(11) . . ? C13 C12 C11 120.06(18) . . ? C13 C12 H12 117.8(13) . . ? C11 C12 H12 122.0(13) . . ? C12 C13 C14 120.41(18) . . ? C12 C13 H13 123.3(18) . . ? C14 C13 H13 116.2(18) . . ? C13 C14 C15 119.98(19) . . ? C13 C14 H14 122.5(14) . . ? C15 C14 H14 117.1(14) . . ? C10 C15 C14 119.72(17) . . ? C10 C15 H15 118.4(12) . . ? C14 C15 H15 121.9(12) . . ? 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 C9 N1 C1 C6 129.41(13) . . . . ? C5 N1 C1 C6 -67.84(14) . . . . ? C9 N1 C1 C2 -102.66(14) . . . . ? C5 N1 C1 C2 60.09(14) . . . . ? N1 C1 C2 C7 -177.16(12) . . . . ? C6 C1 C2 C7 -53.94(17) . . . . ? N1 C1 C2 C8 65.53(14) . . . . ? C6 C1 C2 C8 -171.25(12) . . . . ? N1 C1 C2 C3 -54.75(13) . . . . ? C6 C1 C2 C3 68.46(14) . . . . ? C7 C2 C3 C4 175.76(14) . . . . ? C8 C2 C3 C4 -65.83(18) . . . . ? C1 C2 C3 C4 52.63(15) . . . . ? C2 C3 C4 C5 -52.38(17) . . . . ? C9 N1 C5 C4 104.02(15) . . . . ? C1 N1 C5 C4 -59.62(14) . . . . ? C3 C4 C5 N1 53.89(16) . . . . ? N1 C1 C6 O2 124.28(17) . . . . ? C2 C1 C6 O2 0.4(2) . . . . ? N1 C1 C6 O1 -55.54(15) . . . . ? C2 C1 C6 O1 -179.40(12) . . . . ? C1 N1 C9 O3 161.52(12) . . . . ? C5 N1 C9 O3 -0.3(2) . . . . ? C1 N1 C9 C10 -20.2(2) . . . . ? C5 N1 C9 C10 177.97(12) . . . . ? O3 C9 C10 C15 120.70(17) . . . . ? N1 C9 C10 C15 -57.6(2) . . . . ? O3 C9 C10 C11 -53.8(2) . . . . ? N1 C9 C10 C11 127.90(16) . . . . ? C15 C10 C11 C12 1.7(3) . . . . ? C9 C10 C11 C12 176.28(17) . . . . ? C10 C11 C12 C13 -1.3(3) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? C11 C10 C15 C14 -0.7(3) . . . . ? C9 C10 C15 C14 -175.11(19) . . . . ? C13 C14 C15 C10 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.181 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.033 data_wm242 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 N O3' _chemical_formula_weight 337.40 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 11.1496(7) _cell_length_b 8.7609(6) _cell_length_c 18.8400(12) _cell_angle_alpha 90.00 _cell_angle_beta 105.449(7) _cell_angle_gamma 90.00 _cell_volume 1773.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9607 _exptl_absorpt_correction_T_max 0.9679 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Stoe IPDS' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12820 _diffrn_reflns_av_R_equivalents 0.1085 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.05 _reflns_number_total 3465 _reflns_number_gt 2558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1997)' _computing_cell_refinement 'IPDS (Stoe, 1997)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSTEP (Stoe, 1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0587P)^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 3465 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _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 0.71664(11) 0.35123(13) 0.95368(6) 0.0225(3) Uani 1 1 d . . . O1 O 0.96939(10) 0.29321(13) 0.97915(6) 0.0326(3) Uani 1 1 d . . . H1O H 1.049(2) 0.337(3) 0.9900(14) 0.068(7) Uiso 1 1 d . . . O2 O 0.98425(10) 0.30257(13) 1.10048(6) 0.0348(3) Uani 1 1 d . . . O3 O 0.82773(10) 0.55410(12) 1.00680(6) 0.0313(3) Uani 1 1 d . . . C1 C 0.59644(13) 0.28911(16) 0.90973(8) 0.0238(3) Uani 1 1 d . . . H1 H 0.5559(15) 0.3719(18) 0.8762(10) 0.025(4) Uiso 1 1 d . . . C2 C 0.51792(13) 0.25874(17) 0.96397(8) 0.0259(3) Uani 1 1 d . . . H2A H 0.4953(16) 0.3580(19) 0.9810(10) 0.028(4) Uiso 1 1 d . . . H2B H 0.4384(17) 0.209(2) 0.9405(10) 0.033(4) Uiso 1 1 d . . . C3 C 0.58598(13) 0.16112(16) 1.02966(8) 0.0241(3) Uani 1 1 d . . . H3A H 0.6001(14) 0.0549(18) 1.0129(9) 0.022(4) Uiso 1 1 d . . . H3B H 0.5343(16) 0.1527(18) 1.0643(10) 0.028(4) Uiso 1 1 d . . . C4 C 0.71663(12) 0.22213(15) 1.07241(7) 0.0221(3) Uani 1 1 d . . . C5 C 0.78561(12) 0.24705(16) 1.01250(7) 0.0214(3) Uani 1 1 d . . . H5 H 0.7867(13) 0.1480(17) 0.9885(9) 0.017(3) Uiso 1 1 d . . . C6 C 0.92367(13) 0.28879(16) 1.03747(8) 0.0253(3) Uani 1 1 d . . . C7 C 0.74620(13) 0.50076(16) 0.95463(8) 0.0252(3) Uani 1 1 d . . . C8 C 0.68247(19) 0.6016(2) 0.89126(10) 0.0388(4) Uani 1 1 d . . . H8A H 0.670(2) 0.555(2) 0.8440(14) 0.059(6) Uiso 1 1 d . . . H8B H 0.727(2) 0.692(3) 0.8895(15) 0.074(7) Uiso 1 1 d . . . H8C H 0.599(3) 0.636(3) 0.8934(17) 0.092(9) Uiso 1 1 d . . . C9 C 0.61436(14) 0.15350(16) 0.86257(7) 0.0251(3) Uani 1 1 d . . . C10 C 0.72794(15) 0.12719(18) 0.84680(8) 0.0302(3) Uani 1 1 d . . . H10 H 0.8009(19) 0.195(2) 0.8676(11) 0.045(5) Uiso 1 1 d . . . C11 C 0.74262(17) 0.00504(19) 0.80263(9) 0.0363(4) Uani 1 1 d . . . H11 H 0.8238(19) -0.012(2) 0.7941(10) 0.042(5) Uiso 1 1 d . . . C12 C 0.64269(18) -0.09097(18) 0.77247(9) 0.0373(4) Uani 1 1 d . . . H12 H 0.6580(17) -0.175(2) 0.7446(11) 0.037(5) Uiso 1 1 d . . . C13 C 0.52978(17) -0.06457(18) 0.78684(9) 0.0354(4) Uani 1 1 d . . . H13 H 0.461(2) -0.133(2) 0.7678(12) 0.049(6) Uiso 1 1 d . . . C14 C 0.51436(15) 0.05669(17) 0.83116(8) 0.0288(3) Uani 1 1 d . . . H14 H 0.4336(17) 0.0751(19) 0.8412(10) 0.033(4) Uiso 1 1 d . . . C15 C 0.70328(14) 0.37142(17) 1.11222(8) 0.0268(3) Uani 1 1 d . . . H15A H 0.6641(17) 0.451(2) 1.0789(10) 0.033(4) Uiso 1 1 d . . . H15B H 0.7861(18) 0.415(2) 1.1391(11) 0.038(5) Uiso 1 1 d . . . H15C H 0.6513(17) 0.3552(19) 1.1473(11) 0.034(4) Uiso 1 1 d . . . C16 C 0.78224(12) 0.09666(16) 1.12616(8) 0.0224(3) Uani 1 1 d . . . C17 C 0.81664(14) 0.11814(18) 1.20220(8) 0.0282(3) Uani 1 1 d . . . H17 H 0.8015(16) 0.2148(19) 1.2238(9) 0.028(4) Uiso 1 1 d . . . C18 C 0.87276(15) 0.0026(2) 1.25006(9) 0.0347(4) Uani 1 1 d . . . H18 H 0.8934(18) 0.022(2) 1.3045(11) 0.043(5) Uiso 1 1 d . . . C19 C 0.89553(16) -0.1380(2) 1.22329(9) 0.0364(4) Uani 1 1 d . . . H19 H 0.9331(18) -0.215(2) 1.2550(12) 0.043(5) Uiso 1 1 d . . . C20 C 0.86242(17) -0.16261(19) 1.14774(10) 0.0367(4) Uani 1 1 d . . . H20 H 0.8773(19) -0.262(2) 1.1272(11) 0.048(5) Uiso 1 1 d . . . C21 C 0.80631(15) -0.04641(17) 1.10003(9) 0.0294(3) Uani 1 1 d . . . H21 H 0.7819(18) -0.067(2) 1.0467(11) 0.041(5) 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 0.0238(6) 0.0231(6) 0.0171(6) 0.0010(4) -0.0007(4) -0.0068(5) O1 0.0255(6) 0.0460(6) 0.0268(6) -0.0064(5) 0.0075(4) -0.0121(5) O2 0.0265(6) 0.0503(7) 0.0221(6) -0.0010(5) -0.0033(4) -0.0110(5) O3 0.0340(6) 0.0306(5) 0.0277(6) -0.0035(4) 0.0052(5) -0.0138(4) C1 0.0227(7) 0.0247(7) 0.0187(7) 0.0032(5) -0.0035(5) -0.0049(6) C2 0.0216(7) 0.0280(7) 0.0246(7) 0.0007(6) -0.0003(6) -0.0033(6) C3 0.0218(7) 0.0282(7) 0.0213(7) 0.0016(5) 0.0041(6) -0.0044(6) C4 0.0209(7) 0.0254(7) 0.0179(7) 0.0002(5) 0.0019(5) -0.0036(5) C5 0.0209(7) 0.0234(7) 0.0172(7) 0.0003(5) 0.0003(5) -0.0050(5) C6 0.0246(7) 0.0274(7) 0.0222(7) -0.0020(6) 0.0034(6) -0.0067(6) C7 0.0269(7) 0.0252(7) 0.0242(7) 0.0000(5) 0.0077(6) -0.0055(6) C8 0.0467(10) 0.0294(8) 0.0356(10) 0.0084(7) 0.0026(7) -0.0074(8) C9 0.0314(7) 0.0258(7) 0.0141(7) 0.0054(5) -0.0010(5) -0.0054(6) C10 0.0346(8) 0.0345(8) 0.0196(7) 0.0006(6) 0.0037(6) -0.0066(7) C11 0.0435(10) 0.0413(9) 0.0236(8) 0.0004(6) 0.0079(7) -0.0009(7) C12 0.0586(11) 0.0288(8) 0.0213(8) -0.0007(6) 0.0050(7) -0.0027(7) C13 0.0485(10) 0.0299(8) 0.0207(8) 0.0000(6) -0.0035(7) -0.0136(7) C14 0.0341(8) 0.0280(7) 0.0189(7) 0.0041(6) -0.0023(6) -0.0071(6) C15 0.0307(8) 0.0272(7) 0.0207(7) -0.0009(6) 0.0038(6) -0.0018(6) C16 0.0193(6) 0.0282(7) 0.0185(7) 0.0019(5) 0.0029(5) -0.0049(5) C17 0.0300(8) 0.0326(8) 0.0204(7) -0.0003(6) 0.0037(6) -0.0031(6) C18 0.0360(8) 0.0448(9) 0.0199(8) 0.0050(6) 0.0015(6) -0.0015(7) C19 0.0358(9) 0.0396(9) 0.0301(9) 0.0123(7) 0.0027(7) 0.0051(7) C20 0.0423(10) 0.0328(8) 0.0344(9) 0.0048(7) 0.0091(7) 0.0069(7) C21 0.0337(8) 0.0315(8) 0.0213(7) 0.0014(6) 0.0042(6) 0.0001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.3498(19) . ? N1 C1 1.4788(17) . ? N1 C5 1.4827(17) . ? O1 C6 1.3293(18) . ? O1 H1O 0.94(3) . ? O2 C6 1.2054(18) . ? O3 C7 1.2389(18) . ? C1 C9 1.528(2) . ? C1 C2 1.536(2) . ? C1 H1 0.988(17) . ? C2 C3 1.529(2) . ? C2 H2A 0.983(17) . ? C2 H2B 0.981(19) . ? C3 C4 1.5592(19) . ? C3 H3A 1.009(16) . ? C3 H3B 0.981(18) . ? C4 C15 1.535(2) . ? C4 C16 1.5408(19) . ? C4 C5 1.5412(19) . ? C5 C6 1.5292(19) . ? C5 H5 0.980(15) . ? C7 C8 1.503(2) . ? C8 H8A 0.96(2) . ? C8 H8B 0.94(3) . ? C8 H8C 0.99(3) . ? C9 C10 1.395(2) . ? C9 C14 1.400(2) . ? C10 C11 1.392(2) . ? C10 H10 1.00(2) . ? C11 C12 1.391(2) . ? C11 H11 0.97(2) . ? C12 C13 1.376(3) . ? C12 H12 0.948(19) . ? C13 C14 1.390(2) . ? C13 H13 0.96(2) . ? C14 H14 0.982(18) . ? C15 H15A 0.959(19) . ? C15 H15B 1.00(2) . ? C15 H15C 0.999(19) . ? C16 C17 1.394(2) . ? C16 C21 1.398(2) . ? C17 C18 1.389(2) . ? C17 H17 0.974(17) . ? C18 C19 1.380(3) . ? C18 H18 1.00(2) . ? C19 C20 1.389(2) . ? C19 H19 0.92(2) . ? C20 C21 1.391(2) . ? C20 H20 0.98(2) . ? C21 H21 0.98(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 C7 N1 C1 123.11(12) . . ? C7 N1 C5 120.75(11) . . ? C1 N1 C5 113.84(10) . . ? C6 O1 H1O 112.4(15) . . ? N1 C1 C9 111.86(12) . . ? N1 C1 C2 106.46(11) . . ? C9 C1 C2 115.99(12) . . ? N1 C1 H1 106.3(10) . . ? C9 C1 H1 107.9(10) . . ? C2 C1 H1 107.9(9) . . ? C3 C2 C1 112.80(12) . . ? C3 C2 H2A 110.2(10) . . ? C1 C2 H2A 107.8(10) . . ? C3 C2 H2B 108.2(10) . . ? C1 C2 H2B 112.5(11) . . ? H2A C2 H2B 105.1(14) . . ? C2 C3 C4 114.85(11) . . ? C2 C3 H3A 110.3(9) . . ? C4 C3 H3A 106.0(9) . . ? C2 C3 H3B 109.1(10) . . ? C4 C3 H3B 108.4(10) . . ? H3A C3 H3B 107.9(13) . . ? C15 C4 C16 112.19(11) . . ? C15 C4 C5 111.69(11) . . ? C16 C4 C5 109.89(11) . . ? C15 C4 C3 110.22(12) . . ? C16 C4 C3 108.03(11) . . ? C5 C4 C3 104.49(11) . . ? N1 C5 C6 111.21(11) . . ? N1 C5 C4 111.96(11) . . ? C6 C5 C4 117.80(11) . . ? N1 C5 H5 105.5(9) . . ? C6 C5 H5 102.6(8) . . ? C4 C5 H5 106.4(9) . . ? O2 C6 O1 124.99(14) . . ? O2 C6 C5 125.52(13) . . ? O1 C6 C5 109.21(12) . . ? O3 C7 N1 120.10(13) . . ? O3 C7 C8 120.01(14) . . ? N1 C7 C8 119.87(13) . . ? C7 C8 H8A 114.0(13) . . ? C7 C8 H8B 112.4(17) . . ? H8A C8 H8B 106(2) . . ? C7 C8 H8C 113.4(18) . . ? H8A C8 H8C 105(2) . . ? H8B C8 H8C 105(2) . . ? C10 C9 C14 118.40(14) . . ? C10 C9 C1 121.27(13) . . ? C14 C9 C1 120.25(14) . . ? C11 C10 C9 120.83(15) . . ? C11 C10 H10 118.6(11) . . ? C9 C10 H10 120.5(11) . . ? C12 C11 C10 120.02(17) . . ? C12 C11 H11 121.5(11) . . ? C10 C11 H11 118.5(12) . . ? C13 C12 C11 119.56(16) . . ? C13 C12 H12 123.3(11) . . ? C11 C12 H12 117.0(11) . . ? C12 C13 C14 120.85(15) . . ? C12 C13 H13 120.1(12) . . ? C14 C13 H13 119.1(12) . . ? C13 C14 C9 120.32(16) . . ? C13 C14 H14 120.6(10) . . ? C9 C14 H14 119.1(10) . . ? C4 C15 H15A 112.5(11) . . ? C4 C15 H15B 112.1(10) . . ? H15A C15 H15B 104.7(15) . . ? C4 C15 H15C 110.6(10) . . ? H15A C15 H15C 107.0(15) . . ? H15B C15 H15C 109.7(16) . . ? C17 C16 C21 117.18(13) . . ? C17 C16 C4 122.12(13) . . ? C21 C16 C4 120.67(12) . . ? C18 C17 C16 121.47(14) . . ? C18 C17 H17 117.4(10) . . ? C16 C17 H17 121.1(10) . . ? C19 C18 C17 120.55(15) . . ? C19 C18 H18 120.9(11) . . ? C17 C18 H18 118.5(11) . . ? C18 C19 C20 119.23(15) . . ? C18 C19 H19 120.6(13) . . ? C20 C19 H19 120.2(13) . . ? C19 C20 C21 119.98(16) . . ? C19 C20 H20 120.9(12) . . ? C21 C20 H20 119.1(12) . . ? C20 C21 C16 121.59(15) . . ? C20 C21 H21 118.9(11) . . ? C16 C21 H21 119.5(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 C7 N1 C1 C9 129.03(14) . . . . ? C5 N1 C1 C9 -68.10(15) . . . . ? C7 N1 C1 C2 -103.32(15) . . . . ? C5 N1 C1 C2 59.55(15) . . . . ? N1 C1 C2 C3 -52.55(15) . . . . ? C9 C1 C2 C3 72.61(15) . . . . ? C1 C2 C3 C4 53.43(17) . . . . ? C2 C3 C4 C15 68.07(16) . . . . ? C2 C3 C4 C16 -169.04(12) . . . . ? C2 C3 C4 C5 -52.06(16) . . . . ? C7 N1 C5 C6 -36.58(18) . . . . ? C1 N1 C5 C6 160.11(12) . . . . ? C7 N1 C5 C4 97.52(15) . . . . ? C1 N1 C5 C4 -65.79(15) . . . . ? C15 C4 C5 N1 -62.65(14) . . . . ? C16 C4 C5 N1 172.18(10) . . . . ? C3 C4 C5 N1 56.49(14) . . . . ? C15 C4 C5 C6 68.16(16) . . . . ? C16 C4 C5 C6 -57.01(16) . . . . ? C3 C4 C5 C6 -172.70(12) . . . . ? N1 C5 C6 O2 131.96(15) . . . . ? C4 C5 C6 O2 0.8(2) . . . . ? N1 C5 C6 O1 -53.96(16) . . . . ? C4 C5 C6 O1 174.89(12) . . . . ? C1 N1 C7 O3 158.26(13) . . . . ? C5 N1 C7 O3 -3.5(2) . . . . ? C1 N1 C7 C8 -23.4(2) . . . . ? C5 N1 C7 C8 174.87(14) . . . . ? N1 C1 C9 C10 -18.58(18) . . . . ? C2 C1 C9 C10 -140.94(14) . . . . ? N1 C1 C9 C14 164.55(12) . . . . ? C2 C1 C9 C14 42.19(18) . . . . ? C14 C9 C10 C11 -1.8(2) . . . . ? C1 C9 C10 C11 -178.76(14) . . . . ? C9 C10 C11 C12 1.2(2) . . . . ? C10 C11 C12 C13 -0.2(2) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C9 -0.6(2) . . . . ? C10 C9 C14 C13 1.5(2) . . . . ? C1 C9 C14 C13 178.48(13) . . . . ? C15 C4 C16 C17 3.86(18) . . . . ? C5 C4 C16 C17 128.74(14) . . . . ? C3 C4 C16 C17 -117.83(14) . . . . ? C15 C4 C16 C21 -178.11(13) . . . . ? C5 C4 C16 C21 -53.22(16) . . . . ? C3 C4 C16 C21 60.20(17) . . . . ? C21 C16 C17 C18 0.2(2) . . . . ? C4 C16 C17 C18 178.27(14) . . . . ? C16 C17 C18 C19 -0.3(2) . . . . ? C17 C18 C19 C20 0.4(3) . . . . ? C18 C19 C20 C21 -0.4(3) . . . . ? C19 C20 C21 C16 0.2(3) . . . . ? C17 C16 C21 C20 -0.1(2) . . . . ? C4 C16 C21 C20 -178.24(14) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.197 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.050