Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_mexi _database_code_CSD 164901 loop_ _publ_author_name 'Eduardo Gonzalez-Zamora' 'Aude Fayol' 'Michèle Bois-Choussy' 'Angèle Chiaroni' 'Jieping Zhu' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'MEXI01' _chemical_formula_moiety 'C31 H39 N3 O4' _chemical_formula_structural 'C31 H39 N3 O4' _chemical_formula_analytical ? _chemical_formula_sum 'C31 H39 N3 O4' _chemical_formula_weight 517.65 _chemical_melting_point ? _chemical_compound_source 'Chemical synthesis' 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' '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.049(5) _cell_length_b 9.982(5) _cell_length_c 20.886(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.64(3) _cell_angle_gamma 90.00 _cell_volume 2903.0(21) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13968 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour pale yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method ? _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; rea-detectorarea-detector _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius kappaCCD area-detector diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8306 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.82 _reflns_number_total 4665 _reflns_number_gt 3303 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)' ; _computing_data_reduction 'HKL package (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'R3M (Riche, 1983) ORTEP (Johnson, 1965)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w==1/[\s^2^(Fo^2^)+(0.1122P)^2^+1.5059P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0118(37) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4662 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0755 _refine_ls_wR_factor_all 0.2294 _refine_ls_wR_factor_ref 0.1998 _refine_ls_goodness_of_fit_all 1.101 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.130 _refine_ls_restrained_S_obs 1.181 _refine_ls_shift/su_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.6347(2) 0.8991(3) 0.93016(13) 0.0466(7) Uani 1 d . . H1 H 0.6029(2) 0.9825(3) 0.94004(13) 0.056 Uiso 1 calc R . C2 C 0.7451(2) 0.9170(3) 0.94830(12) 0.0437(7) Uani 1 d . . C3 C 0.7923(2) 0.7874(3) 0.92772(14) 0.0472(7) Uani 1 d . . N4 N 0.7846(2) 0.7825(2) 0.86587(11) 0.0491(7) Uani 1 d . . C4a C 0.7325(2) 0.9083(3) 0.84515(13) 0.0437(7) Uani 1 d . . C5 C 0.7504(2) 0.9544(3) 0.77916(13) 0.0482(8) Uani 1 d . . H5 H 0.7362(2) 0.8801(3) 0.74871(13) 0.058 Uiso 1 calc R . N6 N 0.6863(2) 1.0646(3) 0.75879(12) 0.0558(7) Uani 1 d . . HN6 H 0.6994 1.1059 0.7209 0.067 Uiso 1 d . . C6a C 0.5912(2) 1.0646(3) 0.77048(14) 0.0495(8) Uani 1 d . . C7 C 0.5258(3) 1.1530(4) 0.7364(2) 0.0643(9) Uani 1 d . . H7 H 0.5463(3) 1.2081(4) 0.7051(2) 0.077 Uiso 1 calc R . C8 C 0.4330(3) 1.1603(4) 0.7481(2) 0.0808(12) Uani 1 d . . H8 H 0.3907(3) 1.2189(4) 0.7242(2) 0.097 Uiso 1 calc R . C9 C 0.4019(3) 1.0823(5) 0.7944(2) 0.0950(15) Uani 1 d . . H9 H 0.3389(3) 1.0886(5) 0.8031(2) 0.114 Uiso 1 calc R . C10 C 0.4652(3) 0.9933(4) 0.8284(2) 0.0804(12) Uani 1 d . . H10 H 0.4434(3) 0.9390(4) 0.8596(2) 0.096 Uiso 1 calc R . C10a C 0.5599(2) 0.9827(3) 0.81735(14) 0.0504(8) Uani 1 d . . C10b C 0.6272(2) 0.8843(3) 0.85500(13) 0.0471(7) Uani 1 d . . H10B H 0.6084(2) 0.7925(3) 0.84231(13) 0.056 Uiso 1 calc R . C11 C 0.5917(2) 0.7862(4) 0.96330(14) 0.0560(8) Uani 1 d . . O12 O 0.6072(2) 0.6694(3) 0.95533(14) 0.0900(9) Uani 1 d . . O13 O 0.5331(2) 0.8285(3) 1.00371(14) 0.0897(9) Uani 1 d . . C14 C 0.4917(4) 0.7251(5) 1.0406(3) 0.122(2) Uani 1 d . . H14A H 0.4489(20) 0.7656(6) 1.0672(13) 0.147 Uiso 1 calc R . H14B H 0.5420(4) 0.6789(24) 1.0674(13) 0.147 Uiso 1 calc R . H14C H 0.4566(21) 0.6626(20) 1.0115(3) 0.147 Uiso 1 calc R . O15 O 0.76399(13) 1.0027(2) 0.89507(8) 0.0434(5) Uani 1 d . . N16 N 0.7801(2) 0.9663(3) 1.01060(11) 0.0496(7) Uani 1 d . . C17 C 0.7262(3) 1.0729(4) 1.0369(2) 0.0683(10) Uani 1 d . . H17A H 0.6592(3) 1.0475(4) 1.0347(2) 0.082 Uiso 1 calc R . H17B H 0.7300(3) 1.1543(4) 1.0120(2) 0.082 Uiso 1 calc R . C18 C 0.7689(3) 1.0963(6) 1.1067(2) 0.099(2) Uani 1 d . . H18A H 0.7332(3) 1.1667(6) 1.1249(2) 0.119 Uiso 1 calc R . H18B H 0.7626(3) 1.0152(6) 1.1314(2) 0.119 Uiso 1 calc R . O19 O 0.8669(2) 1.1331(3) 1.11235(13) 0.0986(10) Uani 1 d . . C20 C 0.9197(3) 1.0318(5) 1.0862(2) 0.0830(12) Uani 1 d . . H20A H 0.9163(3) 0.9501(5) 1.1109(2) 0.100 Uiso 1 calc R . H20B H 0.9866(3) 1.0585(5) 1.0893(2) 0.100 Uiso 1 calc R . C21 C 0.8813(2) 1.0061(4) 1.01679(15) 0.0600(9) Uani 1 d . . H21A H 0.8877(2) 1.0865(4) 0.99164(15) 0.072 Uiso 1 calc R . H21B H 0.9185(2) 0.9356(4) 0.99989(15) 0.072 Uiso 1 calc R . C22 C 0.8339(3) 0.6799(3) 0.9731(2) 0.0651(9) Uani 1 d . . H22A H 0.8887(3) 0.7164(3) 1.0008(2) 0.078 Uiso 1 calc R . H22B H 0.7864(3) 0.6544(3) 1.0005(2) 0.078 Uiso 1 calc R . C23 C 0.8653(3) 0.5568(3) 0.9406(2) 0.0593(9) Uani 1 d . . C24 C 0.9569(3) 0.5491(4) 0.9232(2) 0.0773(11) Uani 1 d . . H24 H 0.9987(3) 0.6211(4) 0.9318(2) 0.093 Uiso 1 calc R . C25 C 0.9873(4) 0.4365(6) 0.8933(2) 0.0991(15) Uani 1 d . . H25 H 1.0489(4) 0.4330(6) 0.8817(2) 0.119 Uiso 1 calc R . C26 C 0.9275(6) 0.3323(6) 0.8810(2) 0.112(2) Uani 1 d . . H26 H 0.9485(6) 0.2566(6) 0.8611(2) 0.135 Uiso 1 calc R . C27 C 0.8373(5) 0.3348(4) 0.8970(3) 0.108(2) Uani 1 d . . H27 H 0.7967(5) 0.2617(4) 0.8882(3) 0.130 Uiso 1 calc R . C28 C 0.8060(4) 0.4497(4) 0.9271(2) 0.0865(13) Uani 1 d . . H28 H 0.7439(4) 0.4526(4) 0.9378(2) 0.104 Uiso 1 calc R . C29 C 0.8544(2) 0.9948(4) 0.7795(2) 0.0591(9) Uani 1 d . . H29A H 0.8940(2) 0.9328(4) 0.8071(2) 0.071 Uiso 1 calc R . H29B H 0.8630(2) 1.0828(4) 0.7991(2) 0.071 Uiso 1 calc R . C30 C 0.8923(3) 0.9995(4) 0.7149(2) 0.0649(9) Uani 1 d . . H30A H 0.8545(3) 1.0624(4) 0.6866(2) 0.078 Uiso 1 calc R . H30B H 0.8861(3) 0.9118(4) 0.6949(2) 0.078 Uiso 1 calc R . C31 C 0.9999(3) 1.0433(5) 0.7237(2) 0.0854(13) Uani 1 d . . H31A H 1.0030(3) 1.1386(5) 0.7327(2) 0.102 Uiso 1 calc R . H31B H 1.0328(3) 0.9978(5) 0.7614(2) 0.102 Uiso 1 calc R . C32 C 1.0516(3) 1.0170(6) 0.6695(2) 0.105(2) Uani 1 d . . H32A H 1.0207(3) 1.0659(6) 0.6323(2) 0.126 Uiso 1 calc R . H32B H 1.0462(3) 0.9223(6) 0.6593(2) 0.126 Uiso 1 calc R . C33 C 1.1566(4) 1.0539(8) 0.6798(3) 0.145(2) Uani 1 d . . H33A H 1.1876(4) 1.0077(8) 0.7178(3) 0.174 Uiso 1 calc R . H33B H 1.1624(4) 1.1494(8) 0.6880(3) 0.174 Uiso 1 calc R . C34 C 1.2112(5) 1.0181(9) 0.6203(4) 0.175(3) Uani 1 d . . H34A H 1.2717(18) 1.0642(43) 0.6246(14) 0.210 Uiso 1 calc R . H34B H 1.1729(18) 1.0451(47) 0.5809(4) 0.210 Uiso 1 calc R . H34C H 1.2221(33) 0.9232(12) 0.6194(14) 0.210 Uiso 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 C1 0.050(2) 0.050(2) 0.0388(15) 0.0038(13) 0.0051(12) -0.0011(14) C2 0.049(2) 0.049(2) 0.0327(14) -0.0004(13) 0.0049(12) -0.0009(14) C3 0.049(2) 0.049(2) 0.042(2) -0.0002(13) 0.0023(13) 0.0022(14) N4 0.058(2) 0.0478(14) 0.0402(14) -0.0029(11) 0.0008(11) 0.0065(12) C4a 0.053(2) 0.041(2) 0.0358(14) -0.0057(13) 0.0026(12) -0.0013(14) C5 0.060(2) 0.048(2) 0.0364(15) -0.0035(13) 0.0057(13) 0.0022(15) N6 0.061(2) 0.059(2) 0.0481(15) 0.0133(13) 0.0114(12) 0.0014(14) C6a 0.054(2) 0.050(2) 0.042(2) 0.0002(14) -0.0010(14) -0.0029(15) C7 0.074(2) 0.063(2) 0.053(2) 0.014(2) -0.002(2) 0.004(2) C8 0.064(2) 0.099(3) 0.076(3) 0.028(2) -0.003(2) 0.016(2) C9 0.051(2) 0.134(4) 0.099(3) 0.046(3) 0.004(2) 0.017(2) C10 0.055(2) 0.113(3) 0.072(2) 0.036(2) 0.004(2) -0.006(2) C10a 0.049(2) 0.057(2) 0.043(2) 0.0066(14) -0.0038(13) -0.0026(15) C10b 0.053(2) 0.045(2) 0.042(2) -0.0001(13) 0.0012(13) -0.0059(14) C11 0.057(2) 0.067(2) 0.043(2) 0.006(2) 0.0021(15) -0.004(2) O12 0.122(2) 0.062(2) 0.093(2) 0.0046(15) 0.039(2) -0.015(2) O13 0.095(2) 0.087(2) 0.098(2) 0.031(2) 0.052(2) 0.014(2) C14 0.130(4) 0.117(4) 0.137(4) 0.063(4) 0.078(4) 0.016(3) O15 0.0501(12) 0.0449(11) 0.0355(10) -0.0045(8) 0.0067(8) -0.0044(9) N16 0.0521(15) 0.062(2) 0.0346(13) -0.0083(11) 0.0057(10) -0.0022(12) C17 0.062(2) 0.085(3) 0.059(2) -0.027(2) 0.013(2) 0.000(2) C18 0.092(3) 0.141(4) 0.067(3) -0.054(3) 0.023(2) -0.015(3) O19 0.095(2) 0.131(3) 0.068(2) -0.050(2) 0.0060(15) -0.023(2) C20 0.073(2) 0.122(4) 0.051(2) -0.020(2) -0.004(2) -0.009(2) C21 0.052(2) 0.083(2) 0.045(2) -0.012(2) 0.0041(14) -0.008(2) C22 0.084(2) 0.062(2) 0.047(2) 0.004(2) 0.001(2) 0.015(2) C23 0.076(2) 0.050(2) 0.048(2) 0.0070(15) -0.006(2) 0.010(2) C24 0.087(3) 0.072(3) 0.070(2) -0.003(2) 0.001(2) 0.013(2) C25 0.108(4) 0.106(4) 0.083(3) -0.001(3) 0.010(3) 0.045(3) C26 0.170(6) 0.078(4) 0.082(3) -0.009(3) -0.014(4) 0.049(4) C27 0.160(5) 0.052(3) 0.101(4) 0.000(2) -0.024(4) -0.002(3) C28 0.105(3) 0.068(3) 0.082(3) 0.013(2) -0.002(2) -0.005(2) C29 0.058(2) 0.073(2) 0.047(2) 0.002(2) 0.0081(14) 0.000(2) C30 0.073(2) 0.070(2) 0.055(2) 0.003(2) 0.020(2) 0.002(2) C31 0.072(3) 0.110(3) 0.081(3) 0.026(2) 0.033(2) 0.019(2) C32 0.090(3) 0.143(4) 0.084(3) -0.002(3) 0.017(2) -0.001(3) C33 0.092(4) 0.207(7) 0.142(5) -0.024(5) 0.037(3) -0.033(4) C34 0.109(4) 0.244(9) 0.182(7) -0.050(6) 0.058(4) -0.034(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 C1 C11 1.492(4) . ? C1 C2 1.557(4) . ? C1 C10b 1.566(4) . ? C2 N16 1.417(4) . ? C2 O15 1.455(3) . ? C2 C3 1.540(4) . ? C3 N4 1.283(4) . ? C3 C22 1.499(4) . ? N4 C4a 1.489(4) . ? C4a O15 1.431(3) . ? C4a C5 1.506(4) . ? C4a C10b 1.539(4) . ? C5 N6 1.450(4) . ? C5 C29 1.514(4) . ? N6 C6a 1.389(4) . ? C6a C10a 1.391(4) . ? C6a C7 1.398(5) . ? C7 C8 1.359(5) . ? C8 C9 1.358(6) . ? C9 C10 1.384(5) . ? C10 C10a 1.385(5) . ? C10a C10b 1.510(4) . ? C11 O12 1.201(4) . ? C11 O13 1.324(4) . ? O13 C14 1.455(5) . ? N16 C17 1.455(4) . ? N16 C21 1.465(4) . ? C17 C18 1.520(5) . ? C18 O19 1.414(5) . ? O19 C20 1.406(5) . ? C20 C21 1.500(5) . ? C22 C23 1.498(5) . ? C23 C28 1.363(5) . ? C23 C24 1.385(5) . ? C24 C25 1.381(6) . ? C25 C26 1.340(8) . ? C26 C27 1.353(8) . ? C27 C28 1.406(7) . ? C29 C30 1.515(4) . ? C30 C31 1.561(5) . ? C31 C32 1.449(6) . ? C32 C33 1.508(7) . ? C33 C34 1.584(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 C2 115.2(2) . . ? C11 C1 C10b 114.6(2) . . ? C2 C1 C10b 100.8(2) . . ? N16 C2 O15 114.9(2) . . ? N16 C2 C3 116.0(2) . . ? O15 C2 C3 98.7(2) . . ? N16 C2 C1 118.5(2) . . ? O15 C2 C1 99.1(2) . . ? C3 C2 C1 106.7(2) . . ? N4 C3 C22 125.7(3) . . ? N4 C3 C2 109.4(2) . . ? C22 C3 C2 124.8(3) . . ? C3 N4 C4a 103.5(2) . . ? O15 C4a N4 104.6(2) . . ? O15 C4a C5 113.1(2) . . ? N4 C4a C5 112.8(2) . . ? O15 C4a C10b 102.4(2) . . ? N4 C4a C10b 105.9(2) . . ? C5 C4a C10b 116.8(2) . . ? N6 C5 C4a 109.1(2) . . ? N6 C5 C29 111.1(3) . . ? C4a C5 C29 110.9(2) . . ? C6a N6 C5 121.5(2) . . ? N6 C6a C10a 121.7(3) . . ? N6 C6a C7 119.5(3) . . ? C10a C6a C7 118.8(3) . . ? C8 C7 C6a 121.6(3) . . ? C9 C8 C7 120.2(3) . . ? C8 C9 C10 119.2(4) . . ? C9 C10 C10a 121.9(3) . . ? C10 C10a C6a 118.2(3) . . ? C10 C10a C10b 120.8(3) . . ? C6a C10a C10b 121.0(3) . . ? C10a C10b C4a 112.1(2) . . ? C10a C10b C1 114.5(2) . . ? C4a C10b C1 100.4(2) . . ? O12 C11 O13 122.5(3) . . ? O12 C11 C1 125.2(3) . . ? O13 C11 C1 112.3(3) . . ? C11 O13 C14 116.0(3) . . ? C4a O15 C2 95.7(2) . . ? C2 N16 C17 117.8(3) . . ? C2 N16 C21 112.9(2) . . ? C17 N16 C21 108.4(3) . . ? N16 C17 C18 108.4(3) . . ? O19 C18 C17 112.0(3) . . ? C20 O19 C18 109.8(3) . . ? O19 C20 C21 111.0(3) . . ? N16 C21 C20 110.6(3) . . ? C23 C22 C3 114.5(3) . . ? C28 C23 C24 117.8(4) . . ? C28 C23 C22 121.9(4) . . ? C24 C23 C22 120.3(3) . . ? C25 C24 C23 121.2(5) . . ? C26 C25 C24 119.7(5) . . ? C25 C26 C27 121.5(5) . . ? C26 C27 C28 119.0(5) . . ? C23 C28 C27 120.9(5) . . ? C5 C29 C30 117.2(3) . . ? C29 C30 C31 110.7(3) . . ? C32 C31 C30 115.8(4) . . ? C31 C32 C33 115.3(4) . . ? C32 C33 C34 113.6(5) . . ? _refine_diff_density_max 0.710 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.053