Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year 2007 _journal_volume 5 _journal_page_first 609 _publ_contact_author_name 'Darren Dixon' _publ_contact_author_email darren.dixon@manchester.ac.uk loop_ _publ_author_name D.Dixon A.L.Tillman data_dd0601 _database_code_depnum_ccdc_archive 'CCDC 626419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; t-Butyl [3-hydroxy-3-(p-tolyl)-1-phenylpropyl)carbamate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O3' _chemical_formula_sum 'C21 H27 N O3' _chemical_formula_weight 341.44 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 Pna2(1) 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 19.5903(5) _cell_length_b 16.0570(2) _cell_length_c 6.0750(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1910.96(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 21831 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OH hydrogen atom was located and its position was refined satisfactorily. 1037 Friedel pairs were averaged for the refinement. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9683 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2364 _reflns_number_gt 2148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0634P)^2^+0.2013P] 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 -0.2(14) _refine_ls_number_reflns 2364 _refine_ls_number_parameters 233 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 0.04569(8) 0.25499(10) 0.7689(3) 0.0322(4) Uani 1 1 d . . . H1 H 0.0790(15) 0.2396(18) 0.709(6) 0.039 Uiso 1 1 d . . . O2 O 0.14116(8) 0.20431(10) 0.4720(3) 0.0322(4) Uani 1 1 d . . . O3 O 0.15807(8) 0.22283(13) 0.1041(3) 0.0385(4) Uani 1 1 d . . . N1 N 0.05368(9) 0.20028(12) 0.2240(3) 0.0291(4) Uani 1 1 d . . . H1A H 0.0418 0.2127 0.0882 0.035 Uiso 1 1 calc R . . C1 C -0.14942(15) 0.54109(17) 1.1551(5) 0.0472(7) Uani 1 1 d . . . H1C H -0.1981 0.5366 1.1206 0.071 Uiso 1 1 calc R . . H1D H -0.1337 0.5978 1.1241 0.071 Uiso 1 1 calc R . . H1E H -0.1422 0.5284 1.3112 0.071 Uiso 1 1 calc R . . C2 C -0.10964(13) 0.47996(14) 1.0153(4) 0.0361(5) Uani 1 1 d . . . C3 C -0.04915(12) 0.44557(14) 1.0888(4) 0.0352(5) Uani 1 1 d . . . H3 H -0.0316 0.4617 1.2282 0.042 Uiso 1 1 calc R . . C4 C -0.13306(12) 0.45578(16) 0.8084(5) 0.0378(5) Uani 1 1 d . . . H4 H -0.1741 0.4793 0.7527 0.045 Uiso 1 1 calc R . . C5 C -0.01341(12) 0.38788(14) 0.9631(4) 0.0322(5) Uani 1 1 d . . . H5 H 0.0280 0.3652 1.0183 0.039 Uiso 1 1 calc R . . C6 C -0.09778(12) 0.39806(15) 0.6820(4) 0.0352(5) Uani 1 1 d . . . H6 H -0.1152 0.3825 0.5419 0.042 Uiso 1 1 calc R . . C7 C -0.03739(11) 0.36260(13) 0.7568(4) 0.0277(4) Uani 1 1 d . . . C8 C 0.00357(10) 0.30092(13) 0.6205(4) 0.0276(4) Uani 1 1 d . . . H8 H 0.0339 0.3331 0.5190 0.033 Uiso 1 1 calc R . . C9 C -0.04033(10) 0.24224(14) 0.4817(4) 0.0276(4) Uani 1 1 d . . . H9A H -0.0628 0.2747 0.3635 0.033 Uiso 1 1 calc R . . H9B H -0.0766 0.2182 0.5758 0.033 Uiso 1 1 calc R . . C10 C 0.00104(10) 0.17080(13) 0.3770(4) 0.0270(4) Uani 1 1 d . . . H10 H 0.0246 0.1403 0.4987 0.032 Uiso 1 1 calc R . . C11 C -0.04599(10) 0.10953(13) 0.2621(4) 0.0285(4) Uani 1 1 d . . . C12 C -0.06281(12) 0.03492(15) 0.3651(5) 0.0391(5) Uani 1 1 d . . . H12 H -0.0436 0.0218 0.5044 0.047 Uiso 1 1 calc R . . C13 C -0.07454(12) 0.12670(15) 0.0575(4) 0.0348(5) Uani 1 1 d . . . H13 H -0.0637 0.1775 -0.0146 0.042 Uiso 1 1 calc R . . C14 C -0.10787(14) -0.02076(16) 0.2646(6) 0.0484(7) Uani 1 1 d . . . H14 H -0.1197 -0.0712 0.3369 0.058 Uiso 1 1 calc R . . C15 C -0.11876(12) 0.07069(17) -0.0431(5) 0.0426(6) Uani 1 1 d . . . H15 H -0.1376 0.0830 -0.1835 0.051 Uiso 1 1 calc R . . C16 C -0.13515(13) -0.00286(18) 0.0619(6) 0.0493(7) Uani 1 1 d . . . H16 H -0.1654 -0.0412 -0.0062 0.059 Uiso 1 1 calc R . . C17 C 0.11937(11) 0.20898(14) 0.2834(4) 0.0285(4) Uani 1 1 d . . . C18 C 0.23158(11) 0.24005(15) 0.1240(4) 0.0310(5) Uani 1 1 d . . . C19 C 0.26739(14) 0.1653(2) 0.2222(5) 0.0503(7) Uani 1 1 d . . . H19A H 0.2517 0.1146 0.1482 0.075 Uiso 1 1 calc R . . H19B H 0.2569 0.1617 0.3797 0.075 Uiso 1 1 calc R . . H19C H 0.3168 0.1712 0.2025 0.075 Uiso 1 1 calc R . . C20 C 0.25211(13) 0.25147(19) -0.1151(5) 0.0437(6) Uani 1 1 d . . . H20A H 0.2410 0.2009 -0.1981 0.066 Uiso 1 1 calc R . . H20B H 0.3013 0.2620 -0.1239 0.066 Uiso 1 1 calc R . . H20C H 0.2273 0.2989 -0.1777 0.066 Uiso 1 1 calc R . . C21 C 0.24354(17) 0.31860(19) 0.2573(6) 0.0568(8) Uani 1 1 d . . . H21A H 0.2299 0.3090 0.4104 0.085 Uiso 1 1 calc R . . H21B H 0.2164 0.3642 0.1955 0.085 Uiso 1 1 calc R . . H21C H 0.2921 0.3334 0.2519 0.085 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 0.0315(8) 0.0448(9) 0.0205(7) 0.0000(7) -0.0009(6) 0.0074(6) O2 0.0287(8) 0.0452(9) 0.0226(8) 0.0029(7) -0.0014(7) 0.0005(6) O3 0.0257(8) 0.0668(11) 0.0229(8) 0.0052(8) 0.0003(6) 0.0002(7) N1 0.0263(9) 0.0408(10) 0.0203(9) 0.0032(7) -0.0003(7) 0.0007(7) C1 0.0578(16) 0.0394(14) 0.0444(15) -0.0052(12) 0.0108(13) 0.0047(11) C2 0.0455(13) 0.0291(11) 0.0338(12) 0.0001(10) 0.0070(10) -0.0040(9) C3 0.0484(13) 0.0318(11) 0.0254(11) -0.0016(9) 0.0001(10) -0.0060(9) C4 0.0375(12) 0.0392(12) 0.0367(13) -0.0012(11) -0.0019(11) 0.0050(10) C5 0.0395(11) 0.0313(11) 0.0258(11) 0.0004(9) -0.0047(10) -0.0025(9) C6 0.0374(11) 0.0411(13) 0.0269(11) -0.0043(10) -0.0040(10) 0.0012(10) C7 0.0323(10) 0.0274(10) 0.0234(10) 0.0004(9) 0.0014(9) -0.0043(8) C8 0.0295(10) 0.0323(10) 0.0211(9) 0.0024(8) -0.0015(8) -0.0019(8) C9 0.0270(9) 0.0330(11) 0.0229(10) -0.0005(9) 0.0007(9) 0.0008(8) C10 0.0277(10) 0.0316(10) 0.0219(9) 0.0016(9) 0.0007(8) 0.0008(8) C11 0.0261(10) 0.0312(10) 0.0283(11) -0.0028(10) 0.0033(9) 0.0012(8) C12 0.0427(13) 0.0359(12) 0.0386(13) -0.0013(11) 0.0031(11) 0.0019(10) C13 0.0345(11) 0.0393(12) 0.0304(12) -0.0033(10) -0.0022(10) -0.0023(9) C14 0.0510(14) 0.0305(12) 0.0638(18) -0.0049(13) 0.0061(15) -0.0060(10) C15 0.0352(12) 0.0543(16) 0.0383(13) -0.0153(12) -0.0050(11) 0.0025(10) C16 0.0416(13) 0.0416(14) 0.0647(19) -0.0223(14) -0.0031(13) -0.0036(11) C17 0.0286(10) 0.0338(11) 0.0231(10) 0.0019(9) 0.0005(9) 0.0035(8) C18 0.0236(10) 0.0448(12) 0.0247(10) 0.0013(10) 0.0018(9) -0.0013(8) C19 0.0363(13) 0.0711(19) 0.0434(15) 0.0104(14) 0.0031(12) 0.0173(12) C20 0.0336(12) 0.0691(18) 0.0285(13) 0.0014(13) 0.0038(10) -0.0033(11) C21 0.0706(19) 0.0547(17) 0.0451(17) -0.0127(15) 0.0222(15) -0.0212(14) _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 C8 1.428(3) . ? O1 H1 0.79(3) . ? O2 C17 1.225(3) . ? O3 C17 1.345(3) . ? O3 C18 1.471(3) . ? N1 C17 1.344(3) . ? N1 C10 1.467(3) . ? N1 H1A 0.8800 . ? C1 C2 1.514(3) . ? C1 H1C 0.9800 . ? C1 H1D 0.9800 . ? C1 H1E 0.9800 . ? C2 C3 1.382(3) . ? C2 C4 1.393(4) . ? C3 C5 1.390(3) . ? C3 H3 0.9500 . ? C4 C6 1.388(3) . ? C4 H4 0.9500 . ? C5 C7 1.399(3) . ? C5 H5 0.9500 . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 C8 1.520(3) . ? C8 C9 1.529(3) . ? C8 H8 1.0000 . ? C9 C10 1.542(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.518(3) . ? C10 H10 1.0000 . ? C11 C13 1.390(3) . ? C11 C12 1.391(3) . ? C12 C14 1.397(4) . ? C12 H12 0.9500 . ? C13 C15 1.390(3) . ? C13 H13 0.9500 . ? C14 C16 1.373(5) . ? C14 H14 0.9500 . ? C15 C16 1.380(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C18 C19 1.513(4) . ? C18 C21 1.517(4) . ? C18 C20 1.519(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 O1 H1 111(2) . . ? C17 O3 C18 121.06(17) . . ? C17 N1 C10 122.45(19) . . ? C17 N1 H1A 118.8 . . ? C10 N1 H1A 118.8 . . ? C2 C1 H1C 109.5 . . ? C2 C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? C2 C1 H1E 109.5 . . ? H1C C1 H1E 109.5 . . ? H1D C1 H1E 109.5 . . ? C3 C2 C4 117.6(2) . . ? C3 C2 C1 121.3(2) . . ? C4 C2 C1 121.2(2) . . ? C2 C3 C5 121.4(2) . . ? C2 C3 H3 119.3 . . ? C5 C3 H3 119.3 . . ? C6 C4 C2 121.4(2) . . ? C6 C4 H4 119.3 . . ? C2 C4 H4 119.3 . . ? C3 C5 C7 121.1(2) . . ? C3 C5 H5 119.5 . . ? C7 C5 H5 119.5 . . ? C4 C6 C7 121.1(2) . . ? C4 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C5 117.4(2) . . ? C6 C7 C8 122.6(2) . . ? C5 C7 C8 120.0(2) . . ? O1 C8 C7 107.30(18) . . ? O1 C8 C9 110.79(17) . . ? C7 C8 C9 113.89(17) . . ? O1 C8 H8 108.2 . . ? C7 C8 H8 108.2 . . ? C9 C8 H8 108.2 . . ? C8 C9 C10 112.97(17) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N1 C10 C11 110.16(19) . . ? N1 C10 C9 113.01(17) . . ? C11 C10 C9 110.66(16) . . ? N1 C10 H10 107.6 . . ? C11 C10 H10 107.6 . . ? C9 C10 H10 107.6 . . ? C13 C11 C12 118.5(2) . . ? C13 C11 C10 121.8(2) . . ? C12 C11 C10 119.7(2) . . ? C11 C12 C14 120.3(3) . . ? C11 C12 H12 119.9 . . ? C14 C12 H12 119.9 . . ? C15 C13 C11 121.0(2) . . ? C15 C13 H13 119.5 . . ? C11 C13 H13 119.5 . . ? C16 C14 C12 120.3(3) . . ? C16 C14 H14 119.9 . . ? C12 C14 H14 119.9 . . ? C16 C15 C13 119.7(3) . . ? C16 C15 H15 120.2 . . ? C13 C15 H15 120.2 . . ? C14 C16 C15 120.2(2) . . ? C14 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O2 C17 N1 125.4(2) . . ? O2 C17 O3 124.8(2) . . ? N1 C17 O3 109.8(2) . . ? O3 C18 C19 109.7(2) . . ? O3 C18 C21 110.6(2) . . ? C19 C18 C21 112.2(2) . . ? O3 C18 C20 101.73(18) . . ? C19 C18 C20 110.5(2) . . ? C21 C18 C20 111.7(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C2 C3 C5 -1.1(3) . . . . ? C1 C2 C3 C5 178.4(2) . . . . ? C3 C2 C4 C6 1.2(3) . . . . ? C1 C2 C4 C6 -178.2(2) . . . . ? C2 C3 C5 C7 0.1(3) . . . . ? C2 C4 C6 C7 -0.4(4) . . . . ? C4 C6 C7 C5 -0.5(3) . . . . ? C4 C6 C7 C8 -178.4(2) . . . . ? C3 C5 C7 C6 0.7(3) . . . . ? C3 C5 C7 C8 178.6(2) . . . . ? C6 C7 C8 O1 -158.8(2) . . . . ? C5 C7 C8 O1 23.4(3) . . . . ? C6 C7 C8 C9 -35.8(3) . . . . ? C5 C7 C8 C9 146.4(2) . . . . ? O1 C8 C9 C10 -48.9(3) . . . . ? C7 C8 C9 C10 -169.96(18) . . . . ? C17 N1 C10 C11 -137.9(2) . . . . ? C17 N1 C10 C9 97.8(2) . . . . ? C8 C9 C10 N1 -62.0(3) . . . . ? C8 C9 C10 C11 173.89(18) . . . . ? N1 C10 C11 C13 -48.5(3) . . . . ? C9 C10 C11 C13 77.2(3) . . . . ? N1 C10 C11 C12 133.2(2) . . . . ? C9 C10 C11 C12 -101.1(2) . . . . ? C13 C11 C12 C14 -0.5(3) . . . . ? C10 C11 C12 C14 177.8(2) . . . . ? C12 C11 C13 C15 -0.2(3) . . . . ? C10 C11 C13 C15 -178.5(2) . . . . ? C11 C12 C14 C16 1.0(4) . . . . ? C11 C13 C15 C16 0.5(4) . . . . ? C12 C14 C16 C15 -0.6(4) . . . . ? C13 C15 C16 C14 -0.1(4) . . . . ? C10 N1 C17 O2 -9.9(3) . . . . ? C10 N1 C17 O3 169.45(19) . . . . ? C18 O3 C17 O2 -4.6(3) . . . . ? C18 O3 C17 N1 175.98(19) . . . . ? C17 O3 C18 C19 63.2(3) . . . . ? C17 O3 C18 C21 -61.0(3) . . . . ? C17 O3 C18 C20 -179.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.274 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.089