Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' _publ_contact_autor ; Thorsten Bach Institut f\"ur Organische Chemie und Biochemie Lehrstuhl I Technische Universit\"at M\"unchen Lichtenbergstr. 4 85747 Garching Germany ; _publ_contact_author_phone 'int. 89-289-13330' _publ_contact_author_fax 'int. 89-289-13315' _publ_contact_author_email thorsten.bach@ch.tum.de _publ_requested_coeditor_name ; responsible for X-ray: Prof. Dr. B. Neum\"uller Fachbereich Chemie Universit\"at Marburg Hans-Meerwein-Strasse 35032 Marburg Germany neumuell@chemie.uni-marburg.de ; # 2. TITLE AND AUTHOR LIST _publ_section_title ; Intermolecular hydrogen binding of a host and a prochiral imidazolidinone: Entantioselective Norrish-Yang cyclisation in solution ; loop_ _publ_author_name _publ_author_address 'Bach, T.' ; Institut f\"ur Organische Chemie und Biochemie Lehrstuhl I Technische Universit\"at M\"unchen Lichtenbergstr. 4 85747 Garching Germany ; 'Aechtner, T.' ; Institut f\"ur Organische Chemie und Biochemie Lehrstuhl I Technische Universit\"at M\"unchen Lichtenbergstr. 4 85747 Garching Germany ; 'Neum\"uller, B.' ; Fachbereich Chemie Universit\"at Marburg Hans-Meerwein-Strasse 35032 Marburg Germany ; #============================================================================== data_kaep6 _database_code_CSD 156228 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O4' _chemical_formula_weight 366.41 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 8.946(1) _cell_length_b 12.500(1) _cell_length_c 16.350(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1828.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 38.0 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.758 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details '9 psi-scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'CAD4 (Enraf-Nonius)' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '7200 s' _diffrn_standards_decay_% 0 _diffrn_reflns_number 3696 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 69.93 _reflns_number_total 3399 _reflns_number_gt 3209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPRESS (Enraf-Nonius)' _computing_cell_refinement 'EXPRESS (Enraf-Nonius)' _computing_data_reduction 'XCAD4 (Univ. of Marburg)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' 'PLATON-98 (Spek, 1998)' _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^)+(0.0628P)^2^+0.2170P] 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 'free refinement' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(4) _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 0.05(18) _refine_ls_number_reflns 3399 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.003 _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 -0.28026(14) 0.81648(11) 0.12244(8) 0.0364(3) Uani 1 1 d . . . H1 H -0.285(4) 0.882(3) 0.130(2) 0.106(13) Uiso 1 1 d . . . O2 O 0.33125(12) 0.73836(11) 0.15333(7) 0.0367(3) Uani 1 1 d . . . O3 O 0.11986(14) 0.58932(10) 0.35106(8) 0.0378(3) Uani 1 1 d . . . O4 O 0.39733(13) 0.52105(9) 0.34225(8) 0.0339(3) Uani 1 1 d . . . N1 N 0.11587(15) 0.83846(11) 0.15727(9) 0.0314(3) Uani 1 1 d . . . N2 N 0.14133(15) 0.70989(11) 0.25016(8) 0.0285(3) Uani 1 1 d . . . C1 C -0.12727(18) 0.79052(13) 0.11285(10) 0.0289(3) Uani 1 1 d . . . C11 C -0.11802(19) 0.67058(13) 0.09831(9) 0.0285(3) Uani 1 1 d . . . C12 C -0.2282(2) 0.60364(15) 0.13044(12) 0.0384(4) Uani 1 1 d . . . H121 H -0.310(2) 0.6334(17) 0.1576(13) 0.034(5) Uiso 1 1 d . . . C13 C -0.2198(3) 0.49354(16) 0.11954(12) 0.0458(5) Uani 1 1 d . . . H131 H -0.297(3) 0.4503(19) 0.1447(15) 0.052(6) Uiso 1 1 d . . . C14 C -0.1019(3) 0.44943(15) 0.07750(12) 0.0444(5) Uani 1 1 d . . . H141 H -0.095(3) 0.372(2) 0.0636(19) 0.074(8) Uiso 1 1 d . . . C15 C 0.0081(2) 0.51481(17) 0.04593(13) 0.0466(5) Uani 1 1 d . . . H151 H 0.090(3) 0.4876(18) 0.0136(15) 0.053(6) Uiso 1 1 d . . . C16 C -0.0002(2) 0.62482(15) 0.05675(11) 0.0366(4) Uani 1 1 d . . . H161 H 0.073(3) 0.671(2) 0.0300(15) 0.056(7) Uiso 1 1 d . . . C2 C -0.0509(2) 0.85754(15) 0.04505(11) 0.0359(4) Uani 1 1 d . . . H21 H -0.059(2) 0.8177(18) -0.0086(14) 0.043(6) Uiso 1 1 d . . . H22 H -0.110(3) 0.9258(19) 0.0413(13) 0.049(6) Uiso 1 1 d . . . C3 C 0.1120(2) 0.87595(16) 0.07188(12) 0.0392(4) Uani 1 1 d . . . H31 H 0.188(2) 0.8341(18) 0.0414(13) 0.040(5) Uiso 1 1 d . . . H32 H 0.140(3) 0.954(2) 0.0663(17) 0.062(7) Uiso 1 1 d . . . C4 C -0.03415(19) 0.82460(13) 0.18950(10) 0.0296(3) Uani 1 1 d . . . H41 H -0.073(2) 0.8914(16) 0.2086(12) 0.031(5) Uiso 1 1 d . . . C5 C -0.01386(18) 0.74594(14) 0.26059(10) 0.0300(3) Uani 1 1 d . . . H51 H -0.023(2) 0.7790(15) 0.3133(12) 0.029(5) Uiso 1 1 d . . . H52 H -0.087(2) 0.6847(17) 0.2594(12) 0.035(5) Uiso 1 1 d . . . C6 C 0.21069(17) 0.76032(13) 0.18263(9) 0.0283(3) Uani 1 1 d . . . C7 C 0.20036(18) 0.63498(13) 0.30259(10) 0.0277(3) Uani 1 1 d . . . C8 C 0.36950(18) 0.61984(13) 0.30153(10) 0.0283(3) Uani 1 1 d . . . H81 H 0.406(2) 0.6177(16) 0.2455(12) 0.027(4) Uiso 1 1 d . . . C81 C 0.44392(17) 0.71260(12) 0.34589(10) 0.0285(3) Uani 1 1 d . . . C82 C 0.4080(2) 0.73311(14) 0.42786(11) 0.0371(4) Uani 1 1 d . . . H821 H 0.328(2) 0.6905(17) 0.4530(13) 0.039(5) Uiso 1 1 d . . . C83 C 0.4814(3) 0.81394(17) 0.46991(13) 0.0489(5) Uani 1 1 d . . . H831 H 0.456(3) 0.830(2) 0.5280(17) 0.064(7) Uiso 1 1 d . . . C84 C 0.5887(2) 0.87439(18) 0.43104(16) 0.0535(6) Uani 1 1 d . . . H841 H 0.640(3) 0.934(2) 0.4608(16) 0.064(8) Uiso 1 1 d . . . C85 C 0.6230(2) 0.85611(16) 0.34981(15) 0.0493(5) Uani 1 1 d . . . H851 H 0.702(3) 0.899(2) 0.3195(18) 0.070(8) Uiso 1 1 d . . . C86 C 0.55054(19) 0.77530(14) 0.30696(13) 0.0368(4) Uani 1 1 d . . . H861 H 0.577(2) 0.7615(17) 0.2509(14) 0.041(5) Uiso 1 1 d . . . C9 C 0.5512(2) 0.49109(16) 0.33764(15) 0.0412(4) Uani 1 1 d . . . H91 H 0.562(3) 0.418(2) 0.3628(14) 0.050(6) Uiso 1 1 d . . . H92 H 0.619(3) 0.545(2) 0.3687(14) 0.052(6) Uiso 1 1 d . . . H93 H 0.580(3) 0.490(2) 0.2828(17) 0.054(7) 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 0.0304(6) 0.0358(7) 0.0429(7) -0.0019(5) -0.0025(5) 0.0071(5) O2 0.0283(6) 0.0465(7) 0.0353(6) 0.0078(5) 0.0026(5) -0.0027(5) O3 0.0355(6) 0.0404(7) 0.0375(6) 0.0112(5) 0.0039(5) -0.0005(5) O4 0.0321(6) 0.0255(6) 0.0441(6) 0.0054(5) 0.0005(5) 0.0032(5) N1 0.0319(7) 0.0321(7) 0.0303(7) 0.0065(6) -0.0034(6) -0.0039(6) N2 0.0280(6) 0.0315(7) 0.0260(6) 0.0032(5) -0.0009(5) -0.0002(5) C1 0.0284(8) 0.0303(8) 0.0280(7) 0.0004(6) -0.0021(6) 0.0036(7) C11 0.0303(8) 0.0313(8) 0.0240(7) -0.0011(6) -0.0041(6) 0.0019(7) C12 0.0423(9) 0.0367(10) 0.0363(10) -0.0065(7) 0.0082(8) -0.0012(8) C13 0.0582(12) 0.0359(10) 0.0433(11) -0.0036(8) 0.0070(10) -0.0109(9) C14 0.0604(12) 0.0297(9) 0.0431(11) -0.0074(7) -0.0043(10) 0.0034(8) C15 0.0467(11) 0.0450(11) 0.0483(12) -0.0125(9) 0.0030(9) 0.0118(9) C16 0.0346(9) 0.0390(9) 0.0361(9) -0.0058(7) 0.0016(7) -0.0003(7) C2 0.0397(9) 0.0367(10) 0.0315(9) 0.0068(7) -0.0061(7) 0.0002(8) C3 0.0400(9) 0.0417(10) 0.0360(10) 0.0134(8) -0.0036(8) -0.0053(8) C4 0.0323(8) 0.0274(8) 0.0292(8) -0.0004(6) -0.0016(6) 0.0004(6) C5 0.0282(8) 0.0363(9) 0.0256(8) 0.0001(7) -0.0006(6) 0.0017(7) C6 0.0278(7) 0.0297(8) 0.0274(7) 0.0003(6) -0.0032(6) -0.0075(6) C7 0.0299(8) 0.0264(8) 0.0268(7) -0.0011(6) -0.0005(6) -0.0028(6) C8 0.0320(8) 0.0251(7) 0.0276(8) 0.0019(6) -0.0005(7) 0.0021(6) C81 0.0295(7) 0.0249(7) 0.0312(8) -0.0004(6) -0.0047(6) 0.0065(6) C82 0.0468(10) 0.0329(9) 0.0316(9) 0.0006(7) -0.0055(7) 0.0077(8) C83 0.0636(13) 0.0447(11) 0.0384(10) -0.0119(8) -0.0169(9) 0.0160(10) C84 0.0482(11) 0.0413(11) 0.0710(15) -0.0180(10) -0.0233(11) 0.0042(9) C85 0.0346(9) 0.0406(10) 0.0728(14) -0.0087(10) -0.0051(10) -0.0042(8) C86 0.0307(8) 0.0344(10) 0.0453(10) -0.0030(8) 0.0008(7) -0.0009(7) C9 0.0349(9) 0.0333(10) 0.0553(12) 0.0030(9) 0.0017(9) 0.0068(8) _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 1.415(2) . ? O2 C6 1.212(2) . ? O3 C7 1.213(2) . ? O4 C8 1.425(2) . ? O4 C9 1.429(2) . ? N1 C6 1.358(2) . ? N1 C4 1.452(2) . ? N1 C3 1.473(2) . ? N2 C7 1.375(2) . ? N2 C6 1.415(2) . ? N2 C5 1.470(2) . ? C1 C11 1.520(2) . ? C1 C2 1.548(2) . ? C1 C4 1.564(2) . ? C11 C16 1.379(2) . ? C11 C12 1.395(3) . ? C12 C13 1.390(3) . ? C13 C14 1.375(3) . ? C14 C15 1.379(3) . ? C15 C16 1.388(3) . ? C2 C3 1.539(3) . ? C4 C5 1.533(2) . ? C7 C8 1.525(2) . ? C8 C81 1.521(2) . ? C81 C86 1.389(3) . ? C81 C82 1.402(2) . ? C82 C83 1.387(3) . ? C83 C84 1.377(4) . ? C84 C85 1.382(4) . ? C85 C86 1.390(3) . ? 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 C8 O4 C9 111.77(13) . . ? C6 N1 C4 112.37(13) . . ? C6 N1 C3 122.19(15) . . ? C4 N1 C3 111.09(13) . . ? C7 N2 C6 128.43(13) . . ? C7 N2 C5 119.95(13) . . ? C6 N2 C5 111.61(13) . . ? O1 C1 C11 107.23(14) . . ? O1 C1 C2 112.46(14) . . ? C11 C1 C2 113.44(14) . . ? O1 C1 C4 111.33(13) . . ? C11 C1 C4 111.40(13) . . ? C2 C1 C4 101.02(13) . . ? C16 C11 C12 118.48(16) . . ? C16 C11 C1 121.86(16) . . ? C12 C11 C1 119.61(16) . . ? C13 C12 C11 120.51(18) . . ? C14 C13 C12 120.17(19) . . ? C13 C14 C15 119.80(17) . . ? C14 C15 C16 120.08(18) . . ? C11 C16 C15 120.97(18) . . ? C3 C2 C1 107.13(14) . . ? N1 C3 C2 104.18(14) . . ? N1 C4 C5 104.01(13) . . ? N1 C4 C1 103.54(13) . . ? C5 C4 C1 119.72(14) . . ? N2 C5 C4 102.74(13) . . ? O2 C6 N1 126.73(15) . . ? O2 C6 N2 126.72(15) . . ? N1 C6 N2 106.54(13) . . ? O3 C7 N2 119.98(15) . . ? O3 C7 C8 122.54(15) . . ? N2 C7 C8 117.29(14) . . ? O4 C8 C81 111.18(13) . . ? O4 C8 C7 106.00(13) . . ? C81 C8 C7 109.53(13) . . ? C86 C81 C82 119.50(16) . . ? C86 C81 C8 120.81(15) . . ? C82 C81 C8 119.66(16) . . ? C83 C82 C81 119.89(19) . . ? C84 C83 C82 120.1(2) . . ? C83 C84 C85 120.50(19) . . ? C84 C85 C86 120.1(2) . . ? C81 C86 C85 119.97(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 69.93 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.192 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.039