Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_wei8 _database_code_CSD 162661 _journal_coden_Cambridge 182 #------------------------------------------------------------------------- #2 Person making the deposition _publ_contact_author 'Prof Karl Anker Jorgensen' _publ_contact_author_address ; Prof Karl Anker Jorgensen Department of Chemistry Aarhus University Center for Metal Catalyzed Reaction Aarhus C DK-8000 DENMARK ; _publ_contact_author_email ' KAJ@KEMI.AAU.DK' #------------------------------------------------------------------------- #3 Publication details loop_ _publ_author_name 'Wei Zhuang' 'Rita G. Hazell' 'Karl Anker Jorgensen' _journal_name_full 'Chem Comm.' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year '2001' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------- #4 Chemical and physical data _publ_section_references ; Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA. Cascarano,G., Altomare,A.,Giacovazzo,C., Guagliardi,A., Moliterni,A.G.G, Siliqi,D., Burla,M.C., Polidori,G. & Camalli,M. (1996). Acta Cryst. A52. C-50. Hazell,A. (1995). KRYSTAL, An integrated system of crystallographic programs. Aarhus University, Denmark. Siemens (1995) SMART,SAINT and XPREP: Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA. ; #data_wei8 #===================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (S)-(Methyl-phenyl-amino)-N-((S)-1-phenyl-ethyl)-butyramide ; _chemical_formula_sum C19H23N2O _chemical_formula_weight 296.42 #===================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 6(5)' loop_ _symmetry_equiv_pos_as_xyz '+x,+y,+z' '-y,+x-y,2/3+z' '-x+y,-x,1/3+z' '-x,-y,1/2+z' '+y,-x+y,1/6+z' '+x-y,+x,5/6+z' _cell_length_a 10.329(1) _cell_length_b 10.329(1) _cell_length_c 28.108(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 2597(1) _cell_formula_units_Z 6 _cell_measurement_temperature 120 _cell_measurement_reflns_used 3882 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 22.3 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type 'none' _exptl_aabsorpt_process_details 'none' #===================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 29407 _diffrn_reflns_av_R_equivalents 0.155 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.4 _diffrn_reflns_theta_max 25.2 _diffrn_reflns_reduction_process 29407 _reflns_number_total 5067 _diffrn_measured_fraction_theta_max 100 _reflns_number_gt 1824 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #===================================================================== # 8. REFINEMENT DATA _refine_special_details ; ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w== 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^ ; _refine_ls_hydrogen_treatment calculated _refine_ls_extinction_method ; Type 1 Lorentzian isotropic (Becker and Coppens, 1974) ; _refine_ls_extinction_coef 282(41) _refine_ls_number_reflns 1824 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.052 _refine_ls_goodness_of_fit_ref 1.38 _refine_ls_shift/su_max 0.0011 _refine_ls_shift/su_mean 0.0001 _refine_diff_density_max 0.34(6) _refine_diff_density_min -0.43(6) #========================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O1 0.1946(3) 0.0741(3) 0.2498 0.034(2) Uij N1 0.5049(4) 0.2792(4) 0.1680(1) 0.031(3) Uij N6 0.1126(3) 0.0413(3) 0.1730(1) 0.024(2) Uij C1 0.5050(5) 0.3307(5) 0.1197(2) 0.045(4) Uij C2 0.4564(4) 0.3451(4) 0.2056(2) 0.028(3) Uij C3 0.5525(5) 0.5154(5) 0.2084(2) 0.044(4) Uij C4 0.2886(4) 0.2920(4) 0.2002(2) 0.028(3) Uij C5 0.1941(4) 0.1274(4) 0.2099(2) 0.024(3) Uij C7 0.0207(4) -0.1230(4) 0.1770(2) 0.031(3) Uij C8 -0.1010(5) -0.1762(5) 0.1384(2) 0.047(4) Uij C9 0.1100(4) -0.2025(4) 0.1731(2) 0.029(3) Uij C10 0.0412(5) -0.3546(5) 0.1840(2) 0.046(4) Uij C11 0.1200(7) -0.4307(5) 0.1806(2) 0.058(5) Uij C12 0.2655(6) -0.3590(6) 0.1660(2) 0.057(5) Uij C13 0.3367(6) -0.2084(6) 0.1552(2) 0.061(5) Uij C14 0.2582(5) -0.1306(5) 0.1582(2) 0.043(4) Uij C15 0.6083(4) 0.2316(4) 0.1783(2) 0.026(3) Uij C16 0.6213(9) 0.1908(9) 0.2223(2) 0.105(9) Uij C17 0.7207(9) 0.1392(10) 0.2328(2) 0.111(10) Uij C18 0.8064(5) 0.1272(5) 0.1990(2) 0.046(4) Uij C19 0.7929(7) 0.1671(8) 0.1559(2) 0.088(8) Uij C20 0.6951(7) 0.2184(8) 0.1445(2) 0.084(7) Uij H6n 0.118 0.084 0.133 0.029 Uiso H1a 0.603 0.407 0.110 0.054 Uiso H1b 0.438 0.369 0.116 0.054 Uiso H1c 0.475 0.250 0.100 0.054 Uiso H2 0.468 0.307 0.235 0.034 Uiso H3a 0.522 0.559 0.233 0.052 Uiso H3b 0.547 0.557 0.179 0.052 Uiso H3c 0.653 0.542 0.214 0.052 Uiso H4a 0.270 0.313 0.169 0.034 Uiso H4b 0.262 0.345 0.222 0.034 Uiso H7 -0.026 -0.145 0.207 0.035 Uiso H8a -0.160 -0.281 0.141 0.054 Uiso H8b -0.057 -0.149 0.108 0.054 Uiso H8c -0.161 -0.131 0.143 0.054 Uiso H10 -0.060 -0.407 0.194 0.057 Uiso H11 0.071 -0.534 0.189 0.070 Uiso H12 0.319 -0.412 0.164 0.068 Uiso H13 0.439 -0.156 0.146 0.069 Uiso H14 0.307 -0.027 0.150 0.051 Uiso H16 0.563 0.198 0.247 0.127 Uiso H17 0.728 0.113 0.265 0.133 Uiso H18 0.873 0.091 0.207 0.056 Uiso H19 0.852 0.160 0.131 0.101 Uiso H20 0.688 0.243 0.112 0.105 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.041(2) 0.038(2) 0.023(2) 0.020(1) 0.003(1) 0.007(1) N1 0.030(2) 0.038(2) 0.027(2) 0.020(2) 0.003(2) 0.001(2) N6 0.023(2) 0.025(2) 0.024(2) 0.011(2) -0.003(2) 0.001(2) C1 0.050(3) 0.066(3) 0.034(3) 0.040(3) -0.002(2) 0.004(2) C2 0.031(3) 0.031(3) 0.028(2) 0.019(2) -0.003(2) -0.002(2) C3 0.041(3) 0.038(3) 0.053(3) 0.019(3) 0.002(2) -0.005(2) C4 0.030(2) 0.026(2) 0.032(3) 0.015(2) 0.003(2) -0.002(2) C5 0.018(2) 0.027(2) 0.030(2) 0.015(2) 0.008(2) 0.007(2) C7 0.027(2) 0.028(2) 0.029(2) 0.006(2) 0.001(2) 0.003(2) C8 0.031(3) 0.038(3) 0.062(3) 0.010(2) -0.007(2) -0.007(2) C9 0.032(3) 0.027(3) 0.026(2) 0.014(2) -0.006(2) -0.001(2) C10 0.055(3) 0.027(3) 0.042(3) 0.009(2) -0.005(2) 0.003(2) C11 0.087(4) 0.037(3) 0.058(4) 0.038(3) -0.020(3) -0.003(3) C12 0.078(4) 0.047(3) 0.066(4) 0.045(3) -0.009(3) -0.008(3) C13 0.051(3) 0.044(3) 0.091(5) 0.026(3) -0.006(3) -0.011(3) C14 0.055(3) 0.027(3) 0.052(3) 0.024(3) -0.005(2) -0.003(2) C15 0.022(2) 0.027(2) 0.026(2) 0.011(2) -0.003(2) 0.004(2) C16 0.181(7) 0.209(8) 0.040(3) 0.185(7) 0.028(4) 0.023(4) C17 0.207(8) 0.208(8) 0.042(4) 0.198(8) -0.010(4) 0.000(4) C18 0.045(3) 0.054(3) 0.055(3) 0.037(3) 0.008(3) 0.013(3) C19 0.111(5) 0.172(7) 0.052(4) 0.125(6) 0.050(4) 0.052(4) C20 0.110(5) 0.181(7) 0.034(3) 0.127(5) 0.023(3) 0.028(4) #================================================================== # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C5 1.251(4) N1 C15 1.411(5) N1 C1 1.458(5) N1 C2 1.474(5) N6 C5 1.351(5) N6 C7 1.478(5) C2 C3 1.530(6) C2 C4 1.542(5) C4 C5 1.503(5) C7 C9 1.515(6) C7 C8 1.539(5) C9 C14 1.390(6) C9 C10 1.396(6) C10 C11 1.390(7) C11 C12 1.365(7) C12 C13 1.381(7) C13 C14 1.401(6) C15 C16 1.333(7) C15 C20 1.360(6) C16 C17 1.404(7) C17 C18 1.345(7) C18 C19 1.310(6) C19 C20 1.393(7) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C15 117.1(3) C2 N1 C15 120.3(3) C1 N1 C2 116.0(3) C5 N6 C7 121.8(3) N1 C2 C3 113.1(3) N1 C2 C4 110.2(3) C3 C2 C4 112.4(3) C2 C4 C5 111.3(3) O1 C5 N6 122.5(3) O1 C5 C4 121.1(4) N6 C5 C4 116.4(4) N6 C7 C9 113.6(3) N6 C7 C8 107.3(3) C8 C7 C9 111.4(3) C10 C9 C14 118.2(4) C7 C9 C14 122.6(4) C7 C9 C10 119.2(4) C9 C10 C11 120.6(5) C10 C11 C12 120.7(5) C11 C12 C13 120.0(5) C12 C13 C14 119.8(5) C9 C14 C13 120.7(4) C16 C15 C20 116.1(4) N1 C15 C16 121.0(4) N1 C15 C20 122.8(4) C15 C16 C17 121.6(5) C16 C17 C18 121.6(5) C17 C18 C19 116.5(4) C18 C19 C20 123.0(5) C15 C20 C19 121.1(4) #==================================================================