# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address D.J.Aitken ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; L.Drouin ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; S.Goretta ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; R.Guillot ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; J.Ollivier ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; M.Spiga ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; _publ_contact_author_address ;UMR 8182 CNRS Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay B\^at. 420 Universit\'e Paris-Sud 91405 ORSAY Cedex, France. ; _publ_contact_author_email jean.ollivier@u-psud.fr _publ_contact_author_fax +33(1)69156278 _publ_contact_author_name 'Jean Ollivier' data_1067GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 809952' #TrackingRef '- 1067GuillotICMMO.cif' #_database_code_CSD 'CCDC 80995' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C10 H16 N O4, C10 H16 N O' _chemical_formula_sum 'C20 H32 N2 O5' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(1) _chemical_formula_weight 380.48 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1131(17) _cell_length_b 10.109(2) _cell_length_c 25.357(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2079.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 2614 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 21.17 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.986 _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 18000 _diffrn_reflns_av_R_equivalents 0.0900 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 24.26 _reflns_number_total 3359 _reflns_number_gt 2643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0586P)^2^+0.2544P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.7(15) _refine_ls_number_reflns 3359 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3148(3) 0.6275(2) 0.92787(9) 0.0254(6) Uani 1 1 d . . . H1 H 0.2230 0.6103 0.9396 0.038 Uiso 1 1 calc R . . C1 C 0.2022(4) 0.7919(3) 0.86715(12) 0.0181(7) Uani 1 1 d . . . C8 C 0.4979(4) 0.7918(3) 0.89494(12) 0.0181(7) Uani 1 1 d . . . H8 H 0.4997 0.8811 0.8799 0.022 Uiso 1 1 calc R . . C6 C 0.1678(4) 0.9244(3) 0.85545(13) 0.0211(8) Uani 1 1 d . . . H6 H 0.2206 0.9911 0.8742 0.025 Uiso 1 1 calc R . . C4 C -0.0211(4) 0.8596(4) 0.78791(14) 0.0307(9) Uani 1 1 d . . . H4 H -0.0969 0.8814 0.7618 0.037 Uiso 1 1 calc R . . C2 C 0.1261(4) 0.6957(4) 0.83756(13) 0.0247(8) Uani 1 1 d . . . H2 H 0.1499 0.6072 0.8440 0.030 Uiso 1 1 calc R . . C5 C 0.0566(4) 0.9575(4) 0.81641(13) 0.0263(8) Uani 1 1 d . . . H5 H 0.0340 1.0459 0.8093 0.032 Uiso 1 1 calc R . . C7 C 0.3196(4) 0.7610(3) 0.91160(13) 0.0180(7) Uani 1 1 d . . . H7 H 0.2914 0.8170 0.9418 0.022 Uiso 1 1 calc R . . C9 C 0.5631(4) 0.6972(3) 0.85371(13) 0.0255(8) Uani 1 1 d . . . H9A H 0.5649 0.6091 0.8679 0.038 Uiso 1 1 calc R . . H9B H 0.6728 0.7228 0.8439 0.038 Uiso 1 1 calc R . . H9C H 0.4930 0.6996 0.8232 0.038 Uiso 1 1 calc R . . C3 C 0.0148(4) 0.7285(4) 0.79850(13) 0.0280(9) Uani 1 1 d . . . H3 H -0.0363 0.6620 0.7792 0.034 Uiso 1 1 calc R . . N1 N 0.6075(3) 0.7911(2) 0.94211(10) 0.0173(6) Uani 1 1 d . . . H1A H 0.6384 0.7073 0.9489 0.021 Uiso 1 1 calc R . . H1B H 0.5502 0.8205 0.9702 0.021 Uiso 1 1 calc R . . C10 C 0.7577(4) 0.8743(3) 0.93546(14) 0.0242(8) Uani 1 1 d . . . H10A H 0.7257 0.9644 0.9291 0.036 Uiso 1 1 calc R . . H10B H 0.8208 0.8423 0.9061 0.036 Uiso 1 1 calc R . . H10C H 0.8233 0.8699 0.9669 0.036 Uiso 1 1 calc R . . O2 O 0.4487(3) 0.1281(2) 0.91375(9) 0.0220(5) Uani 1 1 d . . . O3 O 0.5763(3) 0.3026(2) 0.87378(8) 0.0255(6) Uani 1 1 d . . . O4 O 0.2402(3) -0.0467(2) 1.03915(9) 0.0223(5) Uani 1 1 d . . . O5 O 0.5024(2) -0.1135(2) 1.03511(9) 0.0216(5) Uani 1 1 d . . . C15 C 0.5129(4) 0.2358(3) 0.91584(13) 0.0206(7) Uani 1 1 d . . . C12 C 0.5490(4) 0.2598(3) 0.82008(13) 0.0215(8) Uani 1 1 d . . . C13 C 0.3661(4) 0.2644(5) 0.80841(15) 0.0426(11) Uani 1 1 d . . . H13A H 0.3241 0.3508 0.8166 0.064 Uiso 1 1 calc R . . H13B H 0.3101 0.1996 0.8295 0.064 Uiso 1 1 calc R . . H13C H 0.3479 0.2458 0.7717 0.064 Uiso 1 1 calc R . . C14 C 0.6404(5) 0.3622(4) 0.78833(15) 0.0367(10) Uani 1 1 d . . . H14A H 0.7554 0.3593 0.7971 0.055 Uiso 1 1 calc R . . H14B H 0.5974 0.4484 0.7962 0.055 Uiso 1 1 calc R . . H14C H 0.6266 0.3441 0.7514 0.055 Uiso 1 1 calc R . . C11 C 0.6209(5) 0.1235(4) 0.81032(16) 0.0449(11) Uani 1 1 d . . . H11A H 0.5546 0.0582 0.8278 0.067 Uiso 1 1 calc R . . H11B H 0.7314 0.1200 0.8238 0.067 Uiso 1 1 calc R . . H11C H 0.6223 0.1059 0.7731 0.067 Uiso 1 1 calc R . . N2 N 0.5370(3) 0.3075(3) 0.95945(10) 0.0217(6) Uani 1 1 d . . . H2A H 0.5965 0.3778 0.9574 0.026 Uiso 1 1 calc R . . C19 C 0.4468(4) 0.0885(3) 1.07931(13) 0.0187(7) Uani 1 1 d . . . H19A H 0.3510 0.1374 1.0913 0.022 Uiso 1 1 calc R . . H19B H 0.5086 0.0608 1.1101 0.022 Uiso 1 1 calc R . . C16 C 0.4679(4) 0.2721(3) 1.00910(12) 0.0209(8) Uani 1 1 d . . . H16 H 0.3472 0.2715 1.0107 0.025 Uiso 1 1 calc R . . C18 C 0.5525(4) 0.3232(3) 1.05680(14) 0.0229(8) Uani 1 1 d . . . H18A H 0.4844 0.3547 1.0856 0.027 Uiso 1 1 calc R . . H18B H 0.6548 0.3712 1.0519 0.027 Uiso 1 1 calc R . . C20 C 0.3911(4) -0.0323(3) 1.04912(13) 0.0198(8) Uani 1 1 d . . . C17 C 0.5531(4) 0.1775(3) 1.04575(13) 0.0207(8) Uani 1 1 d . . . H17 H 0.6574 0.1400 1.0333 0.025 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 0.0138(11) 0.0196(12) 0.0427(16) 0.0090(12) 0.0043(11) -0.0016(10) C1 0.0097(16) 0.0207(18) 0.0239(18) -0.0026(16) 0.0037(14) -0.0028(15) C8 0.0127(16) 0.0145(17) 0.0269(18) 0.0007(14) 0.0009(14) 0.0001(15) C6 0.0081(16) 0.025(2) 0.031(2) -0.0053(16) -0.0001(14) 0.0022(15) C4 0.0118(17) 0.050(2) 0.030(2) 0.000(2) 0.0003(15) -0.0014(18) C2 0.0193(17) 0.0228(19) 0.032(2) -0.0051(17) 0.0048(16) -0.0067(15) C5 0.0154(18) 0.031(2) 0.032(2) -0.0022(18) -0.0013(16) 0.0053(16) C7 0.0138(16) 0.0155(17) 0.0249(18) 0.0008(15) 0.0045(14) -0.0027(14) C9 0.0150(17) 0.032(2) 0.030(2) -0.0031(17) 0.0025(15) -0.0023(17) C3 0.0189(18) 0.035(2) 0.030(2) -0.0051(17) -0.0019(16) -0.0114(17) N1 0.0097(12) 0.0117(14) 0.0304(15) 0.0010(12) 0.0025(12) 0.0000(12) C10 0.0114(16) 0.0179(18) 0.043(2) 0.0073(17) -0.0002(15) -0.0060(15) O2 0.0151(12) 0.0132(12) 0.0376(14) -0.0001(11) 0.0001(10) -0.0064(10) O3 0.0253(13) 0.0257(13) 0.0255(13) 0.0000(11) 0.0000(11) -0.0106(12) O4 0.0093(11) 0.0160(12) 0.0416(14) 0.0031(11) -0.0014(11) 0.0001(9) O5 0.0132(11) 0.0167(12) 0.0349(14) -0.0017(10) 0.0022(10) 0.0057(10) C15 0.0091(16) 0.024(2) 0.0283(19) 0.0043(17) -0.0017(14) 0.0054(16) C12 0.0201(17) 0.0202(18) 0.0243(18) -0.0001(15) 0.0004(15) 0.0000(15) C13 0.023(2) 0.068(3) 0.037(2) 0.012(2) -0.0082(17) 0.000(2) C14 0.047(2) 0.032(2) 0.031(2) 0.0011(19) 0.0069(18) -0.016(2) C11 0.059(3) 0.031(2) 0.044(3) 0.004(2) 0.012(2) 0.014(2) N2 0.0161(13) 0.0191(15) 0.0300(17) 0.0000(13) -0.0025(13) -0.0091(12) C19 0.0131(17) 0.0161(17) 0.0269(19) -0.0004(14) 0.0013(14) 0.0000(14) C16 0.0154(17) 0.0199(18) 0.0275(19) 0.0021(15) -0.0008(15) -0.0058(15) C18 0.0214(18) 0.0138(17) 0.033(2) -0.0031(15) 0.0063(16) -0.0088(14) C20 0.0181(18) 0.0106(16) 0.031(2) 0.0088(16) 0.0034(16) -0.0018(15) C17 0.0104(15) 0.0173(18) 0.034(2) 0.0011(15) 0.0013(15) 0.0023(13) _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 C7 1.412(4) . ? C1 C2 1.375(4) . ? C1 C6 1.400(4) . ? C1 C7 1.508(4) . ? C8 N1 1.490(4) . ? C8 C9 1.513(4) . ? C8 C7 1.538(4) . ? C6 C5 1.381(5) . ? C4 C5 1.378(5) . ? C4 C3 1.383(5) . ? C2 C3 1.380(5) . ? N1 C10 1.491(4) . ? O2 C15 1.208(4) . ? O3 C15 1.363(4) . ? O3 C12 1.446(4) . ? O4 C20 1.258(4) . ? O5 C20 1.272(4) . ? C15 N2 1.337(4) . ? C12 C14 1.506(5) . ? C12 C13 1.514(5) . ? C12 C11 1.517(5) . ? N2 C16 1.424(4) . ? C19 C17 1.510(4) . ? C19 C20 1.510(4) . ? C16 C18 1.483(5) . ? C16 C17 1.502(4) . ? C18 C17 1.499(4) . ? 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 C1 C6 118.1(3) . . ? C2 C1 C7 123.0(3) . . ? C6 C1 C7 118.8(3) . . ? N1 C8 C9 110.0(2) . . ? N1 C8 C7 109.9(2) . . ? C9 C8 C7 113.0(3) . . ? C5 C6 C1 120.9(3) . . ? C5 C4 C3 119.3(3) . . ? C1 C2 C3 121.0(3) . . ? C4 C5 C6 120.1(3) . . ? O1 C7 C1 113.5(3) . . ? O1 C7 C8 107.4(2) . . ? C1 C7 C8 110.3(2) . . ? C2 C3 C4 120.5(3) . . ? C8 N1 C10 113.2(2) . . ? C15 O3 C12 122.1(2) . . ? O2 C15 N2 126.0(3) . . ? O2 C15 O3 125.1(3) . . ? N2 C15 O3 108.9(3) . . ? O3 C12 C14 102.9(3) . . ? O3 C12 C13 109.0(3) . . ? C14 C12 C13 110.9(3) . . ? O3 C12 C11 111.5(3) . . ? C14 C12 C11 110.3(3) . . ? C13 C12 C11 111.9(3) . . ? C15 N2 C16 122.5(3) . . ? C17 C19 C20 111.6(3) . . ? N2 C16 C18 116.8(3) . . ? N2 C16 C17 121.8(3) . . ? C18 C16 C17 60.3(2) . . ? C16 C18 C17 60.5(2) . . ? O4 C20 O5 124.1(3) . . ? O4 C20 C19 119.1(3) . . ? O5 C20 C19 116.8(3) . . ? C18 C17 C16 59.3(2) . . ? C18 C17 C19 118.6(3) . . ? C16 C17 C19 117.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.222 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.060