# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_989GuillotICMMO _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name 'Val\'erie Alezra' _publ_contact_author_address ;Univ. Paris-Sud, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, B\^atiment 410, CNRS, Orsay, 91405 FRANCE. ; _publ_contact_author_email valerie.alezra@u-psud.fr _publ_contact_author_phone '+33 1 69 15 76 50' _publ_contact_author_fax '+33 1 69 15 46 79' loop_ _publ_author_name _publ_author_address 'Bouill\`ere, Francelin' ;Univ. Paris-Sud, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, B\^atiment 410, CNRS, Orsay, 91405 FRANCE. ; 'Guillot, R\'egis' ;Univ. Paris-Sud, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, B\^atiment 410, CNRS, Orsay, 91405 FRANCE. ; 'Alezra, Val\'erie ' ;Univ. Paris-Sud, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, B\^atiment 410, CNRS, Orsay, 91405 FRANCE. ; 'Kouklovsky, Cyrille' ;Univ. Paris-Sud, Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay, UMR 8182, B\^atiment 410, CNRS, Orsay, 91405 FRANCE. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C21 H32 N2 O6' _chemical_formula_sum 'C21 H32 N2 O6' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 100(1) _chemical_formula_weight 408.49 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 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' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1216(3) _cell_length_b 10.4652(6) _cell_length_c 21.3646(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.373(2) _cell_angle_gamma 90.00 _cell_volume 1140.08(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 8501 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 22.92 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21351 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 23.30 _reflns_number_total 1751 _reflns_number_gt 1609 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1967P)^2^+3.8309P] 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 0.019(13) _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 10(10) _refine_ls_number_reflns 1751 _refine_ls_number_parameters 261 _refine_ls_number_restraints 115 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.3263 _refine_ls_wR_factor_gt 0.3160 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.018 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 C5A C 0.647(5) 0.547(2) 0.7709(11) 0.069(2) Uani 0.50 1 d PDU A 1 H5A1 H 0.5161 0.5960 0.7894 0.103 Uiso 0.50 1 calc PR A 1 H5A2 H 0.7069 0.4791 0.7990 0.103 Uiso 0.50 1 calc PR A 1 H5A3 H 0.5738 0.5113 0.7318 0.103 Uiso 0.50 1 calc PR A 1 C18A C 0.934(6) 1.221(3) 0.7902(12) 0.066(8) Uani 0.50 1 d P B 1 H18A H 0.8554 1.1561 0.8139 0.098 Uiso 0.50 1 calc PR B 1 H18B H 0.8641 1.3032 0.8004 0.098 Uiso 0.50 1 calc PR B 1 H18C H 1.1201 1.2211 0.8004 0.098 Uiso 0.50 1 calc PR B 1 C10A C 0.878(16) 1.198(8) 0.727(8) 0.081(9) Uani 0.50 1 d PD B 1 H10A H 0.6861 1.2046 0.7206 0.097 Uiso 0.50 1 calc PR B 1 C10B C 0.821(14) 1.191(8) 0.723(9) 0.081(9) Uani 0.50 1 d PD B 2 H10B H 0.9103 1.1949 0.7661 0.097 Uiso 0.50 1 calc PR B 2 C5B C 0.409(5) 0.591(2) 0.7235(11) 0.069(2) Uani 0.50 1 d PDU A 2 H5B1 H 0.4424 0.5061 0.7091 0.103 Uiso 0.50 1 calc PR A 2 H5B2 H 0.2228 0.6048 0.7216 0.103 Uiso 0.50 1 calc PR A 2 H5B3 H 0.4841 0.6009 0.7660 0.103 Uiso 0.50 1 calc PR A 2 C18B C 0.622(5) 1.240(3) 0.7309(11) 0.062(8) Uani 0.50 1 d P B 2 H18D H 0.6523 1.3284 0.7418 0.094 Uiso 0.50 1 calc PR B 2 H18E H 0.5425 1.1980 0.7642 0.094 Uiso 0.50 1 calc PR B 2 H18F H 0.5072 1.2350 0.6928 0.094 Uiso 0.50 1 calc PR B 2 O5A O 0.874(3) 0.6314(19) 0.7595(8) 0.069(2) Uani 0.50 1 d PDU A 1 O5B O 0.529(3) 0.687(2) 0.6822(8) 0.069(2) Uani 0.50 1 d PDU A 2 C13 C 0.637(3) 0.975(3) 0.9941(5) 0.186(13) Uani 1 1 d GU . . C15 C 0.808(3) 1.073(3) 1.0137(8) 0.236(15) Uani 1 1 d GU . . H15 H 0.8478 1.1361 0.9855 0.283 Uiso 1 1 calc R . . C16 C 0.921(4) 1.076(3) 1.0755(9) 0.253(15) Uani 1 1 d GU . . H16 H 1.0353 1.1421 1.0886 0.303 Uiso 1 1 calc R . . C19 C 0.861(4) 0.982(3) 1.1177(6) 0.246(16) Uani 1 1 d GU . . H19 H 0.9365 0.9844 1.1590 0.295 Uiso 1 1 calc R . . C20 C 0.690(5) 0.884(3) 1.0980(7) 0.294(17) Uani 1 1 d GU . . H20 H 0.6501 0.8207 1.1263 0.353 Uiso 1 1 calc R . . C23 C 0.577(4) 0.880(3) 1.0363(8) 0.270(16) Uani 1 1 d GU . . H23 H 0.4626 0.8147 1.0231 0.324 Uiso 1 1 calc R . . C3 C 1.303(2) 0.9519(13) 0.4810(5) 0.038(2) Uani 1 1 d . . . H3A H 1.1932 0.8798 0.4880 0.056 Uiso 1 1 calc R . . H3B H 1.4416 0.9572 0.5143 0.056 Uiso 1 1 calc R . . H3C H 1.3757 0.9420 0.4416 0.056 Uiso 1 1 calc R . . C2 C 1.1402(14) 1.0728(14) 0.4798(4) 0.0282(18) Uani 1 1 d . . . C4 C 1.3063(17) 1.1929(13) 0.4840(4) 0.028(2) Uani 1 1 d . . . H4A H 1.4167 1.1929 0.5229 0.042 Uiso 1 1 calc R . . H4B H 1.1942 1.2666 0.4824 0.042 Uiso 1 1 calc R . . H4C H 1.4132 1.1954 0.4494 0.042 Uiso 1 1 calc R . . C1 C 0.9442(15) 1.0769(15) 0.4225(4) 0.033(2) Uani 1 1 d . . . H1A H 0.8484 1.1558 0.4220 0.050 Uiso 1 1 calc R . . H1B H 0.8246 1.0065 0.4238 0.050 Uiso 1 1 calc R . . H1C H 1.0348 1.0709 0.3853 0.050 Uiso 1 1 calc R . . O1 O 0.9697(9) 1.0705(12) 0.5317(2) 0.0287(13) Uani 1 1 d . . . C5 C 1.0739(14) 1.0668(14) 0.5924(3) 0.0271(18) Uani 1 1 d . . . O2 O 1.3056(10) 1.0657(13) 0.6096(3) 0.0366(15) Uani 1 1 d . . . N1 N 0.8819(12) 1.0656(14) 0.6302(3) 0.0360(18) Uani 1 1 d . B . H1 H 0.7221 1.0619 0.6138 0.043 Uiso 1 1 calc R . . C6 C 0.9337(19) 1.0703(2) 0.6993(4) 0.038(2) Uani 1 1 d D . . H6 H 1.1223 1.0556 0.7087 0.046 Uiso 1 1 calc R B 1 C8 C 0.895(2) 0.8251(13) 0.6984(5) 0.043(3) Uani 1 1 d D . . H8A H 0.8769 0.8283 0.6528 0.051 Uiso 1 1 calc R B . H8B H 1.0791 0.8133 0.7124 0.051 Uiso 1 1 calc R . . C7 C 0.7955(19) 0.9539(13) 0.7254(4) 0.038(2) Uani 1 1 d . B . H7 H 0.6076 0.9613 0.7123 0.046 Uiso 1 1 calc R . . N2 N 0.8276(15) 0.9521(15) 0.7929(4) 0.046(2) Uani 1 1 d . . . H2 H 0.9837 0.9560 0.8115 0.055 Uiso 1 1 calc R B . C9 C 0.6295(17) 0.9448(15) 0.8275(4) 0.041(2) Uani 1 1 d . B . O4 O 0.7195(14) 0.9413(14) 0.8892(3) 0.061(2) Uani 1 1 d . . . O3 O 0.4029(14) 0.9451(14) 0.8090(3) 0.060(2) Uani 1 1 d . . . C11 C 0.745(3) 0.7189(15) 0.7196(6) 0.069(2) Uani 1 1 d DU A . C12 C 0.968(9) 1.3045(19) 0.6893(12) 0.28(3) Uani 1 1 d . . . H12A H 0.9192 1.2886 0.6455 0.424 Uiso 1 1 calc R B 1 H12B H 1.1551 1.3119 0.6965 0.424 Uiso 1 1 calc R B 1 H12C H 0.8880 1.3826 0.7015 0.424 Uiso 1 1 calc R B 1 C14 C 0.517(3) 0.930(4) 0.9316(7) 0.142(11) Uani 1 1 d . B . H14A H 0.4592 0.8421 0.9340 0.171 Uiso 1 1 calc R . . H14B H 0.3670 0.9828 0.9173 0.171 Uiso 1 1 calc R . . O6B O 0.755(4) 0.687(2) 0.7728(7) 0.069(2) Uani 0.50 1 d PDU A 2 O6A O 0.529(4) 0.696(2) 0.7035(9) 0.069(2) Uani 0.50 1 d PDU A 1 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 C5A 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) C18A 0.093(19) 0.046(14) 0.054(15) -0.024(12) -0.014(13) 0.006(13) C10A 0.16(3) 0.058(11) 0.024(15) 0.014(7) 0.01(3) 0.046(16) C10B 0.16(3) 0.058(11) 0.024(15) 0.014(7) 0.01(3) 0.046(16) C5B 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) C18B 0.069(15) 0.066(16) 0.050(13) -0.035(12) -0.011(11) 0.047(14) O5A 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) O5B 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) C13 0.100(12) 0.41(4) 0.044(8) -0.015(16) 0.015(8) -0.081(19) C15 0.151(18) 0.40(4) 0.141(17) -0.05(3) -0.060(15) -0.04(3) C16 0.170(19) 0.44(4) 0.129(18) -0.06(3) -0.075(16) -0.06(3) C19 0.19(2) 0.47(5) 0.081(14) -0.06(2) 0.021(15) -0.11(3) C20 0.32(3) 0.48(5) 0.076(14) 0.00(2) -0.01(2) -0.14(3) C23 0.30(3) 0.44(4) 0.062(12) 0.00(2) 0.002(17) -0.13(3) C3 0.045(6) 0.023(5) 0.047(6) -0.008(5) 0.013(5) -0.011(5) C2 0.028(4) 0.026(4) 0.031(4) 0.003(5) 0.006(3) -0.001(5) C4 0.023(4) 0.023(5) 0.038(5) -0.003(4) 0.004(4) -0.010(4) C1 0.026(4) 0.043(5) 0.032(4) -0.007(5) 0.009(3) -0.006(5) O1 0.024(3) 0.038(3) 0.024(3) 0.003(4) 0.001(2) -0.003(3) C5 0.028(4) 0.029(4) 0.023(4) 0.001(5) -0.006(3) 0.002(5) O2 0.024(3) 0.047(4) 0.037(3) 0.006(4) -0.008(2) 0.002(3) N1 0.024(3) 0.059(5) 0.024(3) 0.007(5) -0.002(3) 0.016(5) C6 0.053(5) 0.040(5) 0.021(4) -0.003(5) -0.004(4) 0.013(6) C8 0.049(6) 0.042(6) 0.038(6) -0.001(5) 0.013(5) -0.005(5) C7 0.032(5) 0.060(7) 0.022(5) 0.002(5) 0.000(4) 0.023(5) N2 0.034(4) 0.080(7) 0.023(4) 0.000(5) -0.004(3) 0.018(5) C9 0.031(5) 0.056(7) 0.037(5) 0.011(5) 0.003(4) 0.006(5) O4 0.051(4) 0.111(7) 0.022(3) 0.002(4) 0.004(3) -0.012(5) O3 0.049(5) 0.094(7) 0.038(4) 0.010(5) 0.004(3) -0.006(5) C11 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) C12 0.70(8) 0.033(10) 0.15(2) 0.048(12) 0.21(4) 0.13(2) C14 0.076(9) 0.31(4) 0.044(7) 0.010(15) 0.032(7) -0.037(17) O6B 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) O6A 0.079(4) 0.058(4) 0.069(5) -0.006(4) 0.006(4) -0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C5A O5A 1.496(18) . ? C18A C10A 1.38(16) . ? C10A C12 1.47(17) . ? C10A C6 1.4996(11) . ? C10B C18B 1.17(5) . ? C10B C6 1.5005(14) . ? C10B C12 1.62(16) . ? C5B O5B 1.503(18) . ? O5A C11 1.377(16) . ? O5B C11 1.347(17) . ? C13 C15 1.3900 . ? C13 C23 1.3900 . ? C13 C14 1.49(2) . ? C15 C16 1.3900 . ? C16 C19 1.3900 . ? C19 C20 1.3900 . ? C20 C23 1.3900 . ? C3 C2 1.513(15) . ? C2 O1 1.475(9) . ? C2 C1 1.509(11) . ? C2 C4 1.515(13) . ? O1 C5 1.356(9) . ? C5 O2 1.209(9) . ? C5 N1 1.331(10) . ? N1 C6 1.477(10) . ? C6 C7 1.539(15) . ? C8 C11 1.447(17) . ? C8 C7 1.570(15) . ? C7 N2 1.435(12) . ? N2 C9 1.313(12) . ? C9 O3 1.191(11) . ? C9 O4 1.356(11) . ? O4 C14 1.444(14) . ? C11 O6A 1.152(17) . ? C11 O6B 1.182(16) . ? 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 C18A C10A C12 111(4) . . ? C18A C10A C6 121(10) . . ? C12 C10A C6 112(10) . . ? C18B C10B C6 142(6) . . ? C18B C10B C12 101(8) . . ? C6 C10B C12 105(8) . . ? C11 O5A C5A 99.3(16) . . ? C11 O5B C5B 100.2(16) . . ? C15 C13 C23 120.0 . . ? C15 C13 C14 134.2(16) . . ? C23 C13 C14 105.1(17) . . ? C16 C15 C13 120.0 . . ? C15 C16 C19 120.00(6) . . ? C20 C19 C16 120.0 . . ? C19 C20 C23 120.0 . . ? C20 C23 C13 120.0 . . ? O1 C2 C1 102.4(6) . . ? O1 C2 C3 109.6(8) . . ? C1 C2 C3 111.2(8) . . ? O1 C2 C4 109.7(8) . . ? C1 C2 C4 110.6(8) . . ? C3 C2 C4 112.9(6) . . ? C5 O1 C2 120.8(6) . . ? O2 C5 N1 125.1(7) . . ? O2 C5 O1 125.3(7) . . ? N1 C5 O1 109.5(6) . . ? C5 N1 C6 122.2(7) . . ? N1 C6 C10B 109(7) . . ? N1 C6 C10A 113(7) . . ? C10B C6 C10A 12(6) . . ? N1 C6 C7 106.9(8) . . ? C10B C6 C7 110(6) . . ? C10A C6 C7 117(6) . . ? C11 C8 C7 110.2(9) . . ? N2 C7 C6 111.2(9) . . ? N2 C7 C8 110.3(9) . . ? C6 C7 C8 111.7(7) . . ? C9 N2 C7 123.0(8) . . ? O3 C9 N2 126.4(9) . . ? O3 C9 O4 123.8(9) . . ? N2 C9 O4 109.8(8) . . ? C9 O4 C14 114.3(9) . . ? O6A C11 O6B 100.4(17) . . ? O6A C11 O5B 19.6(13) . . ? O6B C11 O5B 117.4(16) . . ? O6A C11 O5A 115.8(17) . . ? O6B C11 O5A 40.7(11) . . ? O5B C11 O5A 121.3(16) . . ? O6A C11 C8 126.2(16) . . ? O6B C11 C8 122.6(14) . . ? O5B C11 C8 116.1(13) . . ? O5A C11 C8 117.8(12) . . ? C10A C12 C10B 10(9) . . ? O4 C14 C13 106.0(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.748 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.100