# SUBMISSION DETAILS _publ_contact_author_name 'Takuji Hirose' _publ_contact_author_email 'hirose@apc.saitama-u.ac.jp' _publ_contact_author_address '255 Shimo-Okubo,Sakura-ku,Saitama,Japan' _publ_contact_author_fax '+81-48-858-9548' _publ_contact_author_phone '+81-48-858-9548' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'J. Org. Chem.' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Solvent-induced reversed stereoselectivity in reciprocal resolutions of mandelic acid and erythro-2-amino-1,2- diphenylethanol ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' Hiroaki Shitara' ; Technical Support Center, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; ; Toshiki Shintani ; ; Saitama Prefectural Koshigayakita Senior High School ; ; Ohdomari,Koshigaya City,Saitama,Japan ; ; Koichi Kodama ; ; Dept. of Applied Chemistry, Graduate School of Engineering, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; ; Takuji Hirose ; ; Dept. of Applied Chemistry, Graduate School of Engineering, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; _publ_section_synopsis ; ENTER SYNOPSIS ; #===================================================================== data_(R)-1_(1R,2S)-2_EtOH #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H29 N O5' _chemical_formula_weight 411.48 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.3357(5) _cell_length_b 14.5791(12) _cell_length_c 27.620(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2148.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9325 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details ? _chemical_absolute_configuration rm _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10287 _diffrn_reflns_av_R_equivalents 0.1789 _diffrn_reflns_av_sigmaI/netI 0.1073 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3790 _reflns_number_gt 3568 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0751P)^2^+0.1155P] 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 0.1(11) _refine_ls_number_reflns 3790 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 O1 O 0.0145(3) 0.43518(12) 0.64747(6) 0.0233(4) Uani 1 1 d . . . O2 O -0.0134(3) 0.42317(12) 0.74337(5) 0.0290(4) Uani 1 1 d . . . O3 O 0.1634(3) 0.51825(11) 0.81951(5) 0.0238(4) Uani 1 1 d . . . O4 O -0.4116(3) 0.44606(11) 0.76590(5) 0.0273(4) Uani 1 1 d . . . C5 C 0.3130(4) 0.49077(14) 0.58919(7) 0.0176(4) Uani 1 1 d . . . C31 C 0.4254(4) 0.36103(14) 0.64513(7) 0.0182(4) Uani 1 1 d . . . H1 H 0.6052 0.3755 0.6383 0.022 Uiso 1 1 calc R . . C7 C -0.3094(4) 0.39685(16) 0.88903(7) 0.0239(5) Uani 1 1 d . . . H2 H -0.4343 0.4433 0.8893 0.029 Uiso 1 1 calc R . . O5 O -0.2527(4) 0.19011(12) 0.71579(6) 0.0397(5) Uani 1 1 d . . . H30 H -0.2305 0.1395 0.7019 0.060 Uiso 1 1 calc R . . N1 N 0.4072(4) 0.33102(14) 0.69717(6) 0.0218(4) Uani 1 1 d . . . C10 C 0.5646(4) 0.57921(15) 0.53376(8) 0.0241(5) Uani 1 1 d . . . H3 H 0.7108 0.6144 0.5274 0.029 Uiso 1 1 calc R . . C11 C -0.1783(4) 0.44870(14) 0.77269(7) 0.0198(4) Uani 1 1 d . . . C12 C -0.0852(4) 0.48306(14) 0.82238(7) 0.0197(4) Uani 1 1 d . . . H4 H -0.1985 0.5336 0.8334 0.024 Uiso 1 1 calc R . . C13 C 0.3479(4) 0.28451(13) 0.61136(7) 0.0175(4) Uani 1 1 d . . . C14 C 0.1411(4) 0.47580(14) 0.55254(8) 0.0210(4) Uani 1 1 d . . . H5 H -0.0048 0.4404 0.5588 0.025 Uiso 1 1 calc R . . C15 C 0.5257(4) 0.54254(14) 0.57983(8) 0.0212(5) Uani 1 1 d . . . H6 H 0.6449 0.5530 0.6048 0.025 Uiso 1 1 calc R . . C16 C 0.4913(4) 0.26853(15) 0.56996(8) 0.0226(5) Uani 1 1 d . . . H7 H 0.6355 0.3049 0.5638 0.027 Uiso 1 1 calc R . . C17 C 0.3921(4) 0.56468(15) 0.49734(8) 0.0240(5) Uani 1 1 d . . . H8 H 0.4183 0.5904 0.4661 0.029 Uiso 1 1 calc R . . C18 C 0.1396(4) 0.23053(15) 0.61970(8) 0.0252(5) Uani 1 1 d . . . H9 H 0.0402 0.2408 0.6477 0.030 Uiso 1 1 calc R . . C19 C -0.1066(4) 0.40424(14) 0.85805(7) 0.0197(4) Uani 1 1 d . . . C20 C 0.0547(5) 0.26165(16) 0.88962(8) 0.0283(5) Uani 1 1 d . . . H10 H 0.1799 0.2153 0.8896 0.034 Uiso 1 1 calc R . . C21 C 0.0735(4) 0.16085(16) 0.58732(9) 0.0276(5) Uani 1 1 d . . . H11 H -0.0694 0.1238 0.5935 0.033 Uiso 1 1 calc R . . C22 C 0.0770(4) 0.33638(15) 0.85887(8) 0.0234(5) Uani 1 1 d . . . H12 H 0.2187 0.3413 0.8382 0.028 Uiso 1 1 calc R . . C23 C 0.1807(4) 0.51243(15) 0.50650(8) 0.0235(5) Uani 1 1 d . . . H13 H 0.0625 0.5015 0.4814 0.028 Uiso 1 1 calc R . . C24 C -0.3314(4) 0.32145(17) 0.91991(9) 0.0289(5) Uani 1 1 d . . . H14 H -0.4723 0.3163 0.9408 0.035 Uiso 1 1 calc R . . C25 C -0.1488(5) 0.25426(16) 0.92023(9) 0.0307(6) Uani 1 1 d . . . H15 H -0.1633 0.2032 0.9414 0.037 Uiso 1 1 calc R . . C26 C 0.4245(5) 0.19978(16) 0.53779(8) 0.0295(5) Uani 1 1 d . . . H16 H 0.5228 0.1896 0.5096 0.035 Uiso 1 1 calc R . . C27 C 0.2170(5) 0.14611(15) 0.54633(9) 0.0285(5) Uani 1 1 d . . . H17 H 0.1724 0.0991 0.5241 0.034 Uiso 1 1 calc R . . C28 C 0.2740(4) 0.45117(15) 0.63948(7) 0.0179(4) Uani 1 1 d . . . H18 H 0.3353 0.4965 0.6639 0.021 Uiso 1 1 calc R . . C29 C -0.2064(5) 0.17998(19) 0.76674(9) 0.0381(6) Uani 1 1 d . . . H19 H -0.0990 0.2312 0.7779 0.046 Uiso 1 1 calc R . . H20 H -0.1142 0.1220 0.7724 0.046 Uiso 1 1 calc R . . C30 C -0.4387(6) 0.1791(2) 0.79530(10) 0.0468(7) Uani 1 1 d . . . H21 H -0.5251 0.2380 0.7916 0.070 Uiso 1 1 calc R . . H22 H -0.3982 0.1692 0.8295 0.070 Uiso 1 1 calc R . . H23 H -0.5476 0.1295 0.7838 0.070 Uiso 1 1 calc R . . H25 H 0.247(5) 0.322(2) 0.7056(12) 0.039(8) Uiso 1 1 d . . . H24 H 0.508(7) 0.283(3) 0.7032(13) 0.051(9) Uiso 1 1 d . . . H26 H 0.481(4) 0.3748(17) 0.7181(9) 0.016(6) Uiso 1 1 d . . . H27 H -0.013(8) 0.437(3) 0.6749(15) 0.069(12) Uiso 1 1 d . . . H29 H 0.248(5) 0.483(2) 0.8018(11) 0.036(8) 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 0.0219(8) 0.0368(9) 0.0112(7) 0.0022(7) 0.0021(6) 0.0017(7) O2 0.0316(8) 0.0430(9) 0.0125(7) -0.0031(7) 0.0036(7) 0.0038(8) O3 0.0291(8) 0.0249(7) 0.0173(7) -0.0036(6) 0.0027(7) -0.0039(7) O4 0.0269(8) 0.0362(9) 0.0188(7) -0.0069(7) -0.0043(7) 0.0041(7) C5 0.0226(9) 0.0182(9) 0.0121(9) -0.0010(8) 0.0010(9) 0.0066(8) C31 0.0216(10) 0.0236(10) 0.0093(9) 0.0016(8) 0.0002(9) 0.0003(8) C7 0.0245(10) 0.0321(11) 0.0151(10) -0.0044(9) -0.0023(9) -0.0002(9) O5 0.0703(13) 0.0311(9) 0.0177(8) 0.0020(7) 0.0062(9) 0.0228(9) N1 0.0291(11) 0.0269(9) 0.0092(8) 0.0004(7) -0.0025(8) 0.0051(9) C10 0.0233(11) 0.0253(10) 0.0237(11) 0.0028(9) 0.0058(10) 0.0000(9) C11 0.0286(11) 0.0208(9) 0.0100(9) 0.0023(8) -0.0007(9) 0.0037(9) C12 0.0255(11) 0.0207(9) 0.0128(9) -0.0021(8) -0.0003(9) 0.0014(8) C13 0.0217(10) 0.0197(9) 0.0111(9) 0.0011(8) -0.0019(8) 0.0033(8) C14 0.0224(10) 0.0242(9) 0.0163(10) -0.0006(8) -0.0004(9) -0.0021(9) C15 0.0231(10) 0.0232(10) 0.0174(10) -0.0002(9) -0.0006(9) 0.0022(9) C16 0.0252(10) 0.0246(10) 0.0179(10) 0.0002(9) 0.0009(9) -0.0040(9) C17 0.0333(12) 0.0244(10) 0.0141(9) 0.0025(8) 0.0051(10) 0.0063(10) C18 0.0286(11) 0.0268(10) 0.0202(10) 0.0022(9) 0.0010(10) -0.0006(10) C19 0.0262(10) 0.0230(10) 0.0098(9) -0.0046(8) -0.0060(9) -0.0036(9) C20 0.0352(12) 0.0252(10) 0.0246(12) 0.0022(10) -0.0072(11) 0.0021(10) C21 0.0282(11) 0.0234(10) 0.0312(12) 0.0050(9) -0.0066(11) -0.0066(9) C22 0.0254(10) 0.0287(11) 0.0161(10) -0.0033(9) -0.0020(9) 0.0015(9) C23 0.0296(11) 0.0276(10) 0.0134(10) 0.0012(9) -0.0014(9) 0.0015(10) C24 0.0268(11) 0.0422(13) 0.0175(10) 0.0001(10) -0.0008(9) -0.0120(11) C25 0.0402(13) 0.0297(11) 0.0221(11) 0.0069(9) -0.0083(11) -0.0149(11) C26 0.0397(13) 0.0310(11) 0.0179(10) -0.0071(10) 0.0027(11) 0.0001(11) C27 0.0382(13) 0.0226(10) 0.0246(12) -0.0038(9) -0.0086(11) -0.0001(10) C28 0.0206(10) 0.0225(10) 0.0106(9) -0.0020(8) -0.0008(8) 0.0003(8) C29 0.0524(16) 0.0418(14) 0.0202(12) 0.0008(11) -0.0057(12) 0.0090(13) C30 0.0604(18) 0.0561(17) 0.0238(13) 0.0113(12) 0.0070(14) 0.0172(15) _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 C28 1.421(3) . ? O2 C11 1.253(3) . ? O3 C12 1.424(3) . ? O4 C11 1.259(3) . ? C5 C14 1.383(3) . ? C5 C15 1.387(3) . ? C5 C28 1.519(3) . ? C31 N1 1.505(2) . ? C31 C13 1.512(3) . ? C31 C28 1.550(3) . ? C7 C19 1.384(3) . ? C7 C24 1.396(3) . ? O5 C29 1.436(3) . ? C10 C17 1.380(3) . ? C10 C15 1.396(3) . ? C11 C12 1.543(3) . ? C12 C19 1.518(3) . ? C13 C18 1.381(3) . ? C13 C16 1.396(3) . ? C14 C23 1.395(3) . ? C16 C26 1.386(3) . ? C17 C23 1.385(3) . ? C18 C21 1.399(3) . ? C19 C22 1.392(3) . ? C20 C25 1.380(3) . ? C20 C22 1.387(3) . ? C21 C27 1.383(4) . ? C24 C25 1.381(3) . ? C26 C27 1.376(3) . ? C29 C30 1.469(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 C14 C5 C15 119.47(19) . . ? C14 C5 C28 121.22(19) . . ? C15 C5 C28 119.31(18) . . ? N1 C31 C13 110.92(16) . . ? N1 C31 C28 108.00(16) . . ? C13 C31 C28 114.89(16) . . ? C19 C7 C24 120.3(2) . . ? C17 C10 C15 120.5(2) . . ? O2 C11 O4 126.09(19) . . ? O2 C11 C12 116.43(19) . . ? O4 C11 C12 117.43(18) . . ? O3 C12 C19 112.26(18) . . ? O3 C12 C11 111.56(17) . . ? C19 C12 C11 107.90(16) . . ? C18 C13 C16 118.88(19) . . ? C18 C13 C31 122.51(18) . . ? C16 C13 C31 118.61(19) . . ? C5 C14 C23 120.4(2) . . ? C5 C15 C10 120.0(2) . . ? C26 C16 C13 120.3(2) . . ? C10 C17 C23 119.65(19) . . ? C13 C18 C21 120.7(2) . . ? C7 C19 C22 119.0(2) . . ? C7 C19 C12 121.3(2) . . ? C22 C19 C12 119.7(2) . . ? C25 C20 C22 120.3(2) . . ? C27 C21 C18 119.8(2) . . ? C20 C22 C19 120.5(2) . . ? C17 C23 C14 120.0(2) . . ? C25 C24 C7 120.2(2) . . ? C20 C25 C24 119.7(2) . . ? C27 C26 C16 120.5(2) . . ? C26 C27 C21 119.8(2) . . ? O1 C28 C5 109.76(17) . . ? O1 C28 C31 110.65(17) . . ? C5 C28 C31 110.06(16) . . ? O5 C29 C30 112.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.228 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.059