# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Dr Zoltan Hell' _publ_contact_author_address ; Department of Organic Chemical Technology Budapest University of Technology and Economics 1521 Budapest P. O. Box 91 HUNGARY ; _publ_contact_author_email ZHELL@MAIL.BME.HU # 2. TITLE AND AUTHOR LIST _publ_section_title ; Modified Mg:Al hydrotalcite in the synthesis of oxazolidin-2-ones ; loop_ _publ_author_name _publ_author_address 'Agnieszka Cwik' ; Department of Organic Chemical Technology Budapest University of Technology and Economics 1521 Budapest P. O. Box 91 Hungary ; 'Aliz Fuchs' ; Research Group for Organic Chemical Technology Hungarian Academy of Sciences 1521 Budapest, Hungary. ; 'Zoltan Hell' ; Department of Organic Chemical Technology Budapest University of Technology and Economics 1521 Budapest P. O. Box 91 Hungary ; 'Ildiko Bojtos' ; Department of Organic Chemical Technology Budapest University of Technology and Economics 1521 Budapest P. O. Box 91 Hungary ; 'Dora Halmai' ; Department of Organic Chemical Technology Budapest University of Technology and Economics 1521 Budapest P. O. Box 91 Hungary ; 'Petra Bombicz' ; Institute of Structural Chemistry Chemical Research Center Hungarian Academy of Sciences 1525 Budapest POB 17. Hungary ; #========================================================================== data_HZ01ref9 _database_code_depnum_ccdc_archive 'CCDC 258502' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4R-(1R-hydroxy-(4-nitrophenyl)-methyl)-1,3-oxazolidin-2-one ; _ccdc_chemical_compound_source_recrystallisation toluene _chemical_name_common ? _chemical_melting_point 449(1) _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 N2 O5' _chemical_formula_weight 238.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 5.6000(10) _cell_length_b 24.290(2) _cell_length_c 7.7400(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.240(4) _cell_angle_gamma 90.00 _cell_volume 1046.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3150 _cell_measurement_theta_min 3.6378 _cell_measurement_theta_max 72.1250 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.67 _exptl_crystal_size_min 0.52 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.059 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_max 0.9630 _exptl_absorpt_correction_T_min 0.9473 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RAXIS conversion' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 10.0000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19078 _diffrn_reflns_av_R_equivalents 0.0989 _diffrn_reflns_av_sigmaI/netI 0.0906 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 71.78 _reflns_number_total 3716 _reflns_number_gt 3290 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process 'Lp corrections applied' _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _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^)+(0.0271P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 -0.14(17) _refine_ls_number_reflns 3716 _refine_ls_number_parameters 335 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _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 O11 O 1.0157(4) 0.42579(8) 0.3657(2) 0.0268(5) Uani 1 1 d . . . O21 O 1.2638(4) 0.35993(7) 0.4832(2) 0.0244(5) Uani 1 1 d . . . O31 O 1.2589(4) 0.38129(8) -0.1556(3) 0.0247(5) Uani 1 1 d . . . H31O H 1.2180 0.3698 -0.2568 0.069(13) Uiso 1 1 calc R . . O41 O 0.4125(4) 0.54886(8) -0.6578(3) 0.0417(7) Uani 1 1 d . . . O51 O 0.6803(4) 0.61060(8) -0.5761(3) 0.0361(6) Uani 1 1 d . . . N11 N 1.2670(5) 0.38814(10) 0.2000(3) 0.0262(7) Uani 1 1 d . . . H11N H 1.378(6) 0.3638(14) 0.169(4) 0.063(13) Uiso 1 1 d . . . N21 N 0.5967(5) 0.56431(9) -0.5682(3) 0.0290(7) Uani 1 1 d . . . C11 C 0.9399(5) 0.44965(10) -0.2139(3) 0.0182(7) Uani 1 1 d . . . C21 C 0.7111(5) 0.43901(10) -0.2964(4) 0.0223(7) Uani 1 1 d . . . H21 H 0.6313 0.4058 -0.2723 0.018(7) Uiso 1 1 calc R . . C31 C 0.5995(5) 0.47637(10) -0.4132(3) 0.0224(7) Uani 1 1 d . . . H31 H 0.4441 0.4691 -0.4708 0.031(8) Uiso 1 1 calc R . . C41 C 0.7185(6) 0.52439(11) -0.4443(4) 0.0215(7) Uani 1 1 d . . . C51 C 0.9451(5) 0.53647(11) -0.3641(4) 0.0231(7) Uani 1 1 d . . . H51 H 1.0233 0.5699 -0.3882 0.028(8) Uiso 1 1 calc R . . C61 C 1.0546(5) 0.49874(10) -0.2480(4) 0.0206(7) Uani 1 1 d . . . H61 H 1.2099 0.5063 -0.1907 0.025(8) Uiso 1 1 calc R . . C71 C 1.0576(5) 0.40676(10) -0.0892(3) 0.0208(7) Uani 1 1 d . . . H71 H 0.9365 0.3777 -0.0705 0.015(7) Uiso 1 1 calc R . . C81 C 1.1534(6) 0.43069(11) 0.0853(4) 0.0241(8) Uani 1 1 d . . . H81 H 1.2699 0.4610 0.0697 0.032(8) Uiso 1 1 calc R . . C91 C 0.9592(6) 0.45056(12) 0.1958(4) 0.0322(8) Uani 1 1 d . . . H91A H 0.9612 0.4912 0.2048 0.047(10) Uiso 1 1 calc R . . H91B H 0.7982 0.4388 0.1434 0.068(12) Uiso 1 1 calc R . . C101 C 1.1923(5) 0.38810(11) 0.3565(4) 0.0214(7) Uani 1 1 d . . . O12 O 0.8549(4) 0.23794(7) 0.2604(2) 0.0309(6) Uani 1 1 d . . . O22 O 0.6103(4) 0.30445(7) 0.1422(2) 0.0278(5) Uani 1 1 d . . . O32 O 0.7152(4) 0.29820(7) 0.8019(3) 0.0252(5) Uani 1 1 d . . . H32O H 0.6736 0.2922 0.9012 0.032(10) Uiso 1 1 calc R . . O42 O 1.4050(4) 0.04884(7) 1.0383(3) 0.0331(6) Uani 1 1 d . . . O52 O 1.5664(4) 0.11401(9) 1.2054(3) 0.0363(6) Uani 1 1 d . . . N12 N 0.6974(5) 0.29520(10) 0.4385(3) 0.0249(7) Uani 1 1 d . . . H12N H 0.625(6) 0.3226(13) 0.467(4) 0.055(12) Uiso 1 1 d . . . N22 N 1.4168(5) 0.09666(9) 1.0892(3) 0.0271(7) Uani 1 1 d . . . C12 C 0.9265(5) 0.20900(10) 0.8308(3) 0.0179(7) Uani 1 1 d . . . C22 C 0.8676(6) 0.15384(10) 0.8388(4) 0.0219(7) Uani 1 1 d . . . H22 H 0.7169 0.1414 0.7849 0.019(7) Uiso 1 1 calc R . . C32 C 1.0262(5) 0.11652(11) 0.9248(3) 0.0243(8) Uani 1 1 d . . . H32 H 0.9880 0.0785 0.9283 0.018(7) Uiso 1 1 calc R . . C42 C 1.2408(5) 0.13633(11) 1.0051(3) 0.0220(7) Uani 1 1 d . . . C52 C 1.3012(5) 0.19158(11) 1.0044(3) 0.0226(8) Uani 1 1 d . . . H52 H 1.4481 0.2042 1.0642 0.027(8) Uiso 1 1 calc R . . C62 C 1.1438(5) 0.22788(11) 0.9150(4) 0.0229(7) Uani 1 1 d . . . H62 H 1.1834 0.2659 0.9108 0.020(8) Uiso 1 1 calc R . . C72 C 0.7580(5) 0.24742(10) 0.7205(4) 0.0200(7) Uani 1 1 d . . . H72 H 0.6013 0.2283 0.6886 0.003(6) Uiso 1 1 calc R . . C82 C 0.8657(6) 0.26287(10) 0.5567(4) 0.0223(8) Uani 1 1 d . . . H82 H 1.0167 0.2844 0.5871 0.015(7) Uiso 1 1 calc R . . C92 C 0.9135(6) 0.21579(12) 0.4351(4) 0.0300(9) Uani 1 1 d . . . H92A H 1.0840 0.2043 0.4536 0.044(10) Uiso 1 1 calc R . . H92B H 0.8108 0.1837 0.4544 0.027(8) Uiso 1 1 calc R . . C102 C 0.7086(6) 0.28222(11) 0.2737(4) 0.0236(8) 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 O11 0.0359(14) 0.0272(11) 0.0176(11) 0.0018(8) 0.0046(10) 0.0110(10) O21 0.0316(13) 0.0251(10) 0.0160(11) 0.0045(8) 0.0003(10) 0.0027(9) O31 0.0284(13) 0.0282(11) 0.0173(12) -0.0016(9) 0.0007(10) 0.0061(9) O41 0.0385(15) 0.0390(13) 0.0423(15) 0.0069(11) -0.0197(13) 0.0043(11) O51 0.0410(15) 0.0242(11) 0.0417(14) 0.0127(10) -0.0019(12) 0.0015(10) N11 0.0334(18) 0.0311(14) 0.0145(14) 0.0036(11) 0.0041(13) 0.0136(12) N21 0.0340(17) 0.0273(14) 0.0252(15) 0.0042(12) 0.0013(13) 0.0073(12) C11 0.0211(17) 0.0194(13) 0.0143(15) -0.0013(11) 0.0029(13) 0.0002(12) C21 0.0271(18) 0.0182(15) 0.0213(17) -0.0014(12) 0.0007(14) -0.0026(12) C31 0.0237(18) 0.0228(14) 0.0197(16) -0.0034(12) -0.0022(14) 0.0032(12) C41 0.0291(19) 0.0189(13) 0.0159(15) 0.0009(11) -0.0012(14) 0.0072(12) C51 0.0296(19) 0.0186(14) 0.0216(17) 0.0007(11) 0.0047(14) -0.0019(12) C61 0.0200(18) 0.0232(14) 0.0183(16) -0.0013(12) 0.0010(14) -0.0007(12) C71 0.0232(18) 0.0178(14) 0.0212(17) -0.0025(12) 0.0019(14) 0.0023(12) C81 0.032(2) 0.0207(14) 0.0182(17) 0.0023(12) -0.0014(14) 0.0053(13) C91 0.044(2) 0.0357(17) 0.0175(17) 0.0063(13) 0.0053(17) 0.0178(16) C101 0.0276(19) 0.0169(13) 0.0193(17) -0.0037(12) 0.0008(15) -0.0024(12) O12 0.0474(16) 0.0299(11) 0.0147(12) 0.0007(9) 0.0006(11) 0.0173(10) O22 0.0354(13) 0.0284(11) 0.0187(11) 0.0035(8) -0.0012(10) 0.0088(9) O32 0.0423(14) 0.0174(9) 0.0159(12) -0.0001(8) 0.0022(11) 0.0052(9) O42 0.0366(15) 0.0217(11) 0.0407(15) 0.0050(10) 0.0032(12) 0.0079(10) O52 0.0341(14) 0.0372(12) 0.0342(13) 0.0081(10) -0.0109(12) 0.0035(10) N12 0.0371(18) 0.0207(13) 0.0160(14) -0.0015(11) -0.0009(13) 0.0098(12) N22 0.0257(17) 0.0287(14) 0.0268(15) 0.0085(11) 0.0026(13) 0.0041(11) C12 0.0219(18) 0.0185(13) 0.0135(16) -0.0005(11) 0.0029(13) 0.0027(12) C22 0.0219(18) 0.0239(15) 0.0195(16) -0.0024(12) 0.0002(14) -0.0011(12) C32 0.034(2) 0.0155(14) 0.0233(17) 0.0018(12) 0.0022(15) -0.0010(13) C42 0.0261(18) 0.0238(14) 0.0156(16) 0.0036(11) 0.0006(14) 0.0068(12) C52 0.0262(18) 0.0231(14) 0.0177(17) -0.0023(12) -0.0021(14) -0.0017(12) C62 0.0296(19) 0.0201(15) 0.0188(16) -0.0005(12) 0.0018(14) -0.0009(13) C72 0.0232(18) 0.0160(14) 0.0199(16) -0.0012(11) -0.0021(14) 0.0013(11) C82 0.0281(19) 0.0192(14) 0.0184(16) 0.0030(12) -0.0027(15) 0.0026(13) C92 0.046(2) 0.0301(17) 0.0142(17) 0.0043(12) 0.0022(16) 0.0117(15) C102 0.0289(19) 0.0217(15) 0.0197(17) -0.0018(11) -0.0003(15) 0.0011(12) _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 O11 C101 1.356(3) . ? O11 C91 1.449(3) . ? O21 C101 1.227(3) . ? O31 C71 1.429(3) . ? O41 N21 1.237(3) . ? O51 N21 1.222(3) . ? N11 C101 1.324(4) . ? N11 C81 1.462(3) . ? N21 C41 1.478(3) . ? C11 C21 1.392(3) . ? C11 C61 1.393(4) . ? C11 C71 1.521(3) . ? C21 C31 1.382(3) . ? C31 C41 1.377(4) . ? C41 C51 1.382(4) . ? C51 C61 1.380(3) . ? C71 C81 1.515(3) . ? C81 C91 1.532(4) . ? O12 C102 1.363(3) . ? O12 C92 1.459(3) . ? O22 C102 1.228(3) . ? O32 C72 1.417(3) . ? O42 N22 1.226(3) . ? O52 N22 1.235(3) . ? N12 C102 1.322(4) . ? N12 C82 1.467(3) . ? N22 C42 1.478(3) . ? C12 C22 1.383(4) . ? C12 C62 1.394(3) . ? C12 C72 1.521(3) . ? C22 C32 1.387(3) . ? C32 C42 1.378(3) . ? C42 C52 1.384(3) . ? C52 C62 1.379(3) . ? C72 C82 1.510(4) . ? C82 C92 1.523(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 C101 O11 C91 108.7(2) . . ? C101 N11 C81 113.3(3) . . ? O51 N21 O41 123.5(2) . . ? O51 N21 C41 118.9(2) . . ? O41 N21 C41 117.6(2) . . ? C21 C11 C61 119.5(2) . . ? C21 C11 C71 118.5(2) . . ? C61 C11 C71 122.0(2) . . ? C31 C21 C11 120.4(3) . . ? C41 C31 C21 118.5(3) . . ? C31 C41 C51 122.7(2) . . ? C31 C41 N21 118.1(2) . . ? C51 C41 N21 119.3(2) . . ? C61 C51 C41 118.2(3) . . ? C51 C61 C11 120.7(3) . . ? O31 C71 C81 105.7(2) . . ? O31 C71 C11 111.9(2) . . ? C81 C71 C11 113.0(2) . . ? N11 C81 C71 111.0(2) . . ? N11 C81 C91 99.9(2) . . ? C71 C81 C91 114.5(3) . . ? O11 C91 C81 106.1(2) . . ? O21 C101 N11 128.6(3) . . ? O21 C101 O11 120.7(3) . . ? N11 C101 O11 110.6(2) . . ? C102 O12 C92 107.3(2) . . ? C102 N12 C82 112.3(3) . . ? O42 N22 O52 124.5(2) . . ? O42 N22 C42 117.8(2) . . ? O52 N22 C42 117.7(2) . . ? C22 C12 C62 119.9(2) . . ? C22 C12 C72 118.9(2) . . ? C62 C12 C72 121.1(2) . . ? C12 C22 C32 120.8(3) . . ? C42 C32 C22 118.0(2) . . ? C32 C42 C52 122.6(2) . . ? C32 C42 N22 118.6(2) . . ? C52 C42 N22 118.8(2) . . ? C62 C52 C42 118.6(3) . . ? C52 C62 C12 120.1(3) . . ? O32 C72 C82 105.0(2) . . ? O32 C72 C12 114.2(2) . . ? C82 C72 C12 110.1(2) . . ? N12 C82 C72 111.6(3) . . ? N12 C82 C92 99.3(2) . . ? C72 C82 C92 116.5(2) . . ? O12 C92 C82 105.0(2) . . ? O22 C102 N12 129.1(3) . . ? O22 C102 O12 120.2(3) . . ? N12 C102 O12 110.7(2) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 71.78 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.200 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.057