Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_oci2 _database_code_CSD 163263 _journal_coden_Cambridge 182 loop_ _publ_author_name 'M.Schmittel' 'A.Haeuseler' 'T.Nilges' 'A.Pfitzner' _publ_contact_author_name 'Prof Michael Schmittel' _publ_contact_author_address ; FB 8 (Chemie - Biologie) Universität Siegen Adolf-Reichwein-Str. Siegen D-57068 GERMANY ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; The Elusive Aldol Reaction of Enolates with Aldolates - A Highly Stereoselective Process Using Three Different Carbonyl Components ; _publ_section_references ; EXPOSE, CELL, INTEGRATE, STOE & CIE GmbH, Darmstadt (Germany), 1996. SHELX 97, G. M. Sheldrick, Universit\"at Goettingen, Germany, 1997. DIAMOND, Ver. 2.1e, K. Brandenburg, Crystal Impact GbR, Darmstadt, Germany, 2001. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Ethyl-3,5-dimethyl-4,6-diphenyl- tetrahydropyran-2,4-diol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 O3' _chemical_formula_weight 326.42 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' '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 n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.9177(9) _cell_length_b 17.2334(10) _cell_length_c 9.4999(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1787.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7998 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 28.0 _exptl_crystal_description isometric _exptl_crystal_colour transparent _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type 'none' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS I' _diffrn_measurement_method 'image plate data from phi scans' _diffrn_standards_decay_% 0 _diffrn_reflns_number 27347 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.11 _reflns_number_total 4247 _reflns_number_gt 3926 _reflns_threshold_expression >2sigma(I) _reflns_d_resolution_high 0.7543 _computing_data_collection 'STOE EXPOSE' _computing_cell_refinement 'STOE CELL' _computing_data_reduction 'STOE INTEGRATE' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND' _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^)+(0.0515P)^2^+0.0609P] 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 SHELXL _refine_ls_extinction_coef 0.0117(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 0.8(6) _refine_ls_number_reflns 4247 _refine_ls_number_parameters 322 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 -0.22822(6) 0.09180(5) 0.85361(8) 0.02143(17) Uani 1 1 d . . . O2 O -0.03994(7) 0.03039(4) 0.88803(10) 0.02342(17) Uani 1 1 d . . . OH2 H 0.0087(15) 0.0302(10) 0.538(2) 0.041(5) Uiso 1 1 d . . . O3 O 0.00708(7) 0.05319(4) 0.62375(9) 0.02003(15) Uani 1 1 d . . . OH3 H -0.0178(17) 0.0202(10) 0.805(2) 0.044(5) Uiso 1 1 d . . . C1 C -0.10198(9) 0.10306(6) 0.88514(12) 0.0188(2) Uani 1 1 d . . . C2 C -0.04417(9) 0.15764(6) 0.77485(11) 0.0179(2) Uani 1 1 d . . . H2 H -0.0930(11) 0.2083(7) 0.7803(15) 0.016(3) Uiso 1 1 d . . . C3 C -0.06179(8) 0.12418(6) 0.62510(12) 0.01724(19) Uani 1 1 d . . . C4 C -0.19971(9) 0.10763(6) 0.59882(11) 0.0184(2) Uani 1 1 d . . . H4 H -0.2440(11) 0.1582(7) 0.5985(15) 0.016(3) Uiso 1 1 d . . . C5 C -0.25297(9) 0.05767(6) 0.71849(13) 0.0196(2) Uani 1 1 d . . . H5 H -0.2140(13) 0.0056(9) 0.7143(17) 0.026(4) Uiso 1 1 d . . . C6 C -0.09904(10) 0.13374(7) 1.03547(13) 0.0246(2) Uani 1 1 d . . . H61 H -0.1396(15) 0.0940(9) 1.0942(18) 0.036(4) Uiso 1 1 d . . . H62 H -0.0109(14) 0.1334(8) 1.0700(19) 0.032(4) Uiso 1 1 d . . . C7 C -0.15550(14) 0.21317(9) 1.05686(17) 0.0371(3) Uani 1 1 d . . . H71 H -0.1553(16) 0.2278(10) 1.156(2) 0.046(5) Uiso 1 1 d . . . H72 H -0.1127(19) 0.2564(13) 1.002(2) 0.060(5) Uiso 1 1 d . . . H73 H -0.2395(17) 0.2130(10) 1.026(2) 0.047(5) Uiso 1 1 d . . . C8 C 0.08985(10) 0.17516(7) 0.80896(14) 0.0256(2) Uani 1 1 d . . . H81 H 0.1270(17) 0.2085(10) 0.735(2) 0.048(5) Uiso 1 1 d . . . H82 H 0.0987(14) 0.2059(9) 0.900(2) 0.038(4) Uiso 1 1 d . . . H83 H 0.1383(15) 0.1253(9) 0.812(2) 0.036(4) Uiso 1 1 d . . . C9 C -0.22113(10) 0.06969(7) 0.45567(13) 0.0248(2) Uani 1 1 d . . . H91 H -0.1811(16) 0.0992(10) 0.377(2) 0.046(5) Uiso 1 1 d . . . H92 H -0.1870(14) 0.0134(9) 0.450(2) 0.037(4) Uiso 1 1 d . . . H93 H -0.3104(15) 0.0676(8) 0.4341(18) 0.032(4) Uiso 1 1 d . . . C10 C -0.01260(9) 0.18078(6) 0.51421(12) 0.0212(2) Uani 1 1 d . . . C11 C 0.08623(11) 0.16163(7) 0.42919(14) 0.0291(3) Uani 1 1 d . . . H111 H 0.1302(16) 0.1118(9) 0.4396(19) 0.037(4) Uiso 1 1 d . . . C12 C 0.12906(12) 0.21392(8) 0.32876(15) 0.0365(3) Uani 1 1 d . . . H121 H 0.1997(18) 0.1962(10) 0.265(2) 0.055(5) Uiso 1 1 d . . . C13 C 0.07558(14) 0.28616(8) 0.31375(16) 0.0391(3) Uani 1 1 d . . . H131 H 0.1078(15) 0.3246(9) 0.243(2) 0.042(4) Uiso 1 1 d . . . C14 C -0.02157(13) 0.30628(8) 0.39933(16) 0.0355(3) Uani 1 1 d . . . H141 H -0.0607(16) 0.3572(10) 0.394(2) 0.043(4) Uiso 1 1 d . . . C15 C -0.06626(11) 0.25396(7) 0.49861(14) 0.0277(2) Uani 1 1 d . . . H151 H -0.1359(15) 0.2685(9) 0.560(2) 0.037(4) Uiso 1 1 d . . . C16 C -0.39101(9) 0.05011(6) 0.70758(12) 0.0218(2) Uani 1 1 d . . . C17 C -0.46722(10) 0.10531(7) 0.76893(14) 0.0259(2) Uani 1 1 d . . . H171 H -0.4334(16) 0.1486(9) 0.824(2) 0.040(4) Uiso 1 1 d . . . C18 C -0.59382(10) 0.10035(8) 0.75372(15) 0.0311(3) Uani 1 1 d . . . H181 H -0.6466(17) 0.1408(10) 0.799(2) 0.048(5) Uiso 1 1 d . . . C19 C -0.64518(10) 0.04095(8) 0.67495(15) 0.0326(3) Uani 1 1 d . . . H191 H -0.7364(14) 0.0381(9) 0.6609(18) 0.032(4) Uiso 1 1 d . . . C20 C -0.57066(11) -0.01425(8) 0.61435(16) 0.0339(3) Uani 1 1 d . . . H201 H -0.6019(16) -0.0554(9) 0.557(2) 0.043(5) Uiso 1 1 d . . . C22 C -0.44385(11) -0.01062(7) 0.63231(15) 0.0292(2) Uani 1 1 d . . . H221 H -0.3894(16) -0.0509(9) 0.589(2) 0.042(5) 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 0.0174(3) 0.0312(4) 0.0156(4) -0.0019(3) 0.0001(3) -0.0013(3) O2 0.0293(4) 0.0241(4) 0.0169(4) 0.0029(3) 0.0001(3) 0.0073(3) O3 0.0223(3) 0.0216(3) 0.0162(4) -0.0021(3) 0.0007(3) 0.0054(3) C1 0.0160(4) 0.0228(4) 0.0175(5) 0.0001(4) -0.0023(4) 0.0030(3) C2 0.0165(4) 0.0204(4) 0.0167(5) -0.0020(4) -0.0003(4) 0.0012(3) C3 0.0172(4) 0.0182(4) 0.0163(5) -0.0005(4) 0.0017(4) 0.0022(3) C4 0.0173(4) 0.0213(4) 0.0166(6) -0.0002(4) 0.0001(4) 0.0008(3) C5 0.0195(4) 0.0227(5) 0.0165(5) -0.0006(4) -0.0008(4) -0.0008(4) C6 0.0228(5) 0.0350(6) 0.0159(6) -0.0030(4) -0.0013(4) 0.0033(4) C7 0.0390(7) 0.0467(7) 0.0258(7) -0.0152(6) -0.0023(5) 0.0144(6) C8 0.0197(5) 0.0324(5) 0.0247(6) -0.0039(5) -0.0019(4) -0.0042(4) C9 0.0224(5) 0.0347(6) 0.0173(6) -0.0032(4) -0.0017(4) -0.0029(4) C10 0.0222(5) 0.0237(5) 0.0176(6) 0.0009(4) -0.0012(4) -0.0047(4) C11 0.0256(5) 0.0336(6) 0.0282(7) 0.0016(5) 0.0066(4) -0.0051(4) C12 0.0338(6) 0.0457(7) 0.0300(8) 0.0026(6) 0.0100(5) -0.0133(5) C13 0.0471(7) 0.0404(7) 0.0297(8) 0.0095(6) 0.0000(6) -0.0203(6) C14 0.0465(7) 0.0279(6) 0.0321(8) 0.0082(5) -0.0039(6) -0.0069(5) C15 0.0323(5) 0.0256(5) 0.0252(6) 0.0036(5) -0.0007(5) -0.0010(4) C16 0.0214(5) 0.0254(5) 0.0186(6) 0.0034(4) -0.0005(4) -0.0032(4) C17 0.0218(5) 0.0275(5) 0.0282(6) -0.0002(4) 0.0000(4) -0.0016(4) C18 0.0217(5) 0.0354(6) 0.0362(8) 0.0037(5) 0.0019(5) -0.0003(4) C19 0.0203(5) 0.0446(7) 0.0329(7) 0.0068(5) -0.0024(5) -0.0080(5) C20 0.0296(6) 0.0417(7) 0.0304(7) -0.0030(6) -0.0027(5) -0.0131(5) C22 0.0269(5) 0.0329(6) 0.0279(7) -0.0053(5) 0.0017(5) -0.0069(4) _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 C1 1.4237(11) . ? O1 C5 1.4376(13) . ? O2 C1 1.4241(12) . ? O3 C3 1.4360(11) . ? C1 C6 1.5232(16) . ? C1 C2 1.5429(15) . ? C2 C8 1.5287(14) . ? C2 C3 1.5470(15) . ? C3 C10 1.5329(14) . ? C3 C4 1.5527(13) . ? C4 C9 1.5269(16) . ? C4 C5 1.5400(15) . ? C5 C16 1.5162(14) . ? C6 C7 1.5150(17) . ? C10 C11 1.3876(16) . ? C10 C15 1.3984(16) . ? C11 C12 1.3932(18) . ? C12 C13 1.382(2) . ? C13 C14 1.381(2) . ? C14 C15 1.3930(18) . ? C16 C17 1.3918(16) . ? C16 C22 1.3925(16) . ? C17 C18 1.3923(15) . ? C18 C19 1.3865(19) . ? C19 C20 1.378(2) . ? C20 C22 1.3964(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 C1 O1 C5 115.18(8) . . ? O1 C1 O2 110.16(8) . . ? O1 C1 C6 105.36(8) . . ? O2 C1 C6 106.09(9) . . ? O1 C1 C2 109.65(8) . . ? O2 C1 C2 110.77(8) . . ? C6 C1 C2 114.62(9) . . ? C8 C2 C1 111.59(9) . . ? C8 C2 C3 112.81(9) . . ? C1 C2 C3 110.26(8) . . ? O3 C3 C10 110.64(8) . . ? O3 C3 C2 105.11(8) . . ? C10 C3 C2 110.56(8) . . ? O3 C3 C4 110.48(8) . . ? C10 C3 C4 110.25(9) . . ? C2 C3 C4 109.69(8) . . ? C9 C4 C5 111.12(8) . . ? C9 C4 C3 111.74(9) . . ? C5 C4 C3 110.49(8) . . ? O1 C5 C16 106.45(9) . . ? O1 C5 C4 111.07(8) . . ? C16 C5 C4 111.89(9) . . ? C7 C6 C1 115.52(10) . . ? C11 C10 C15 118.59(11) . . ? C11 C10 C3 121.40(10) . . ? C15 C10 C3 119.99(10) . . ? C10 C11 C12 120.38(12) . . ? C13 C12 C11 120.76(12) . . ? C14 C13 C12 119.33(12) . . ? C13 C14 C15 120.35(12) . . ? C14 C15 C10 120.57(12) . . ? C17 C16 C22 118.75(10) . . ? C17 C16 C5 120.45(10) . . ? C22 C16 C5 120.77(10) . . ? C16 C17 C18 120.53(11) . . ? C19 C18 C17 120.19(12) . . ? C20 C19 C18 119.76(11) . . ? C19 C20 C22 120.23(12) . . ? C16 C22 C20 120.48(12) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.11 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.154 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.034