# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/260 data_DPG-dCS _audit_creation_method SHELXL-97 _chemical_name_systematic ; D-phenylglycine(1S)-(+)-camphor-10-sulfonate ; _chemical_name_common D-PGd-CS _chemical_melting_point 207 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 N O6 S' _chemical_formula_weight 383.45 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' 'O' 'O' 0.0492 0.0322 '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' 'S' 'S' 0.3331 0.5567 '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 17.527(2) _cell_length_b 15.290(2) _cell_length_c 6.912(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1852.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.857 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 1608 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1800 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 59.96 _reflns_number_total 1608 _reflns_number_gt 1495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(14) _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 0.07(4) _refine_ls_number_reflns 1608 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1551 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.003 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 S1 S 0.21061(7) 0.14275(7) 0.08717(16) 0.0350(4) Uani 1 1 d . . . O2 O 0.1469(2) 0.1384(2) 0.2162(7) 0.0581(11) Uani 1 1 d . . . O3 O 0.2812(2) 0.1282(3) 0.1892(9) 0.0806(16) Uani 1 1 d . . . O4 O 0.2097(5) 0.0840(3) -0.0723(7) 0.119(3) Uani 1 1 d . . . O8 O 0.3559(2) 0.3341(3) 0.1211(5) 0.0504(10) Uani 1 1 d . . . O34 O 0.0381(3) 0.1525(2) 0.6341(8) 0.0765(15) Uani 1 1 d . . . O35 O -0.0318(2) 0.0540(2) 0.7887(7) 0.0582(11) Uani 1 1 d . . . N31 N 0.1528(2) 0.0398(2) 0.5641(6) 0.0366(9) Uani 1 1 d . . . C5 C 0.2126(3) 0.2509(3) 0.0001(8) 0.0416(12) Uani 1 1 d . . . C6 C 0.2740(2) 0.2815(3) -0.1409(6) 0.0258(9) Uani 1 1 d . . . C7 C 0.3387(3) 0.3325(3) -0.0496(7) 0.0335(11) Uani 1 1 d . . . C9 C 0.3761(3) 0.3852(3) -0.2066(9) 0.0460(13) Uani 1 1 d . . . C10 C 0.3272(3) 0.3620(3) -0.3807(7) 0.0403(12) Uani 1 1 d . . . C11 C 0.3488(3) 0.2681(3) -0.4382(7) 0.0435(12) Uani 1 1 d . . . C12 C 0.3158(3) 0.2137(3) -0.2699(7) 0.0354(10) Uani 1 1 d . . . C13 C 0.2464(3) 0.3513(3) -0.2915(7) 0.0346(10) Uani 1 1 d . . . C14 C 0.2145(3) 0.4331(3) -0.1980(9) 0.0516(14) Uani 1 1 d . . . C15 C 0.1875(4) 0.3168(4) -0.4342(9) 0.0599(16) Uani 1 1 d . . . C32 C 0.0800(3) 0.0033(3) 0.6437(7) 0.0351(11) Uani 1 1 d . . . C33 C 0.0269(3) 0.0803(3) 0.6880(7) 0.0417(12) Uani 1 1 d . . . C36 C 0.0437(2) -0.0617(3) 0.5101(7) 0.0319(10) Uani 1 1 d . . . C37 C 0.0237(3) -0.1441(3) 0.5784(7) 0.0374(11) Uani 1 1 d . . . C38 C -0.0121(3) -0.2035(3) 0.4586(8) 0.0421(13) Uani 1 1 d . . . C39 C -0.0278(3) -0.1821(3) 0.2705(9) 0.0451(13) Uani 1 1 d . . . C40 C -0.0080(3) -0.0998(3) 0.2002(8) 0.0451(13) Uani 1 1 d . . . C41 C 0.0272(3) -0.0401(3) 0.3191(7) 0.0371(11) Uani 1 1 d . . . H16 H 0.2165 0.2878 0.1104 0.050 Uiso 1 1 d . . . H17 H 0.1651 0.2607 -0.0622 0.050 Uiso 1 1 d . . . H18 H 0.3743 0.4461 -0.1797 0.055 Uiso 1 1 d . . . H19 H 0.4279 0.3680 -0.2257 0.055 Uiso 1 1 d . . . H20 H 0.3298 0.4029 -0.4837 0.049 Uiso 1 1 d . . . H21 H 0.4023 0.2614 -0.4476 0.052 Uiso 1 1 d . . . H22 H 0.3257 0.2524 -0.5580 0.052 Uiso 1 1 d . . . H23 H 0.2810 0.1710 -0.3169 0.042 Uiso 1 1 d . . . H24 H 0.3555 0.1859 -0.2001 0.042 Uiso 1 1 d . . . H25 H 0.1657 0.4207 -0.1441 0.061 Uiso 1 1 d . . . H26 H 0.2479 0.4522 -0.0985 0.061 Uiso 1 1 d . . . H27 H 0.2095 0.4779 -0.2925 0.061 Uiso 1 1 d . . . H28 H 0.2018 0.2599 -0.4759 0.072 Uiso 1 1 d . . . H29 H 0.1390 0.3142 -0.3728 0.072 Uiso 1 1 d . . . H30 H 0.1847 0.3548 -0.5427 0.072 Uiso 1 1 d . . . H42 H 0.1856 -0.0070 0.5281 0.044 Uiso 1 1 d . . . H43 H 0.1418 0.0744 0.4534 0.044 Uiso 1 1 d . . . H44 H 0.1770 0.0747 0.6594 0.044 Uiso 1 1 d . . . H45 H 0.0914 -0.0256 0.7624 0.042 Uiso 1 1 d . . . H46 H -0.0657 0.0909 0.7835 0.058 Uiso 1 1 d . . . H47 H 0.0348 -0.1598 0.7083 0.045 Uiso 1 1 d . . . H48 H -0.0260 -0.2594 0.5071 0.050 Uiso 1 1 d . . . H49 H -0.0521 -0.2233 0.1882 0.054 Uiso 1 1 d . . . H50 H -0.0190 -0.0850 0.0695 0.054 Uiso 1 1 d . . . H51 H 0.0405 0.0160 0.2706 0.044 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 S1 0.0502(7) 0.0254(6) 0.0296(6) 0.0014(5) 0.0064(5) -0.0058(5) O2 0.053(2) 0.0434(19) 0.078(3) 0.022(2) 0.024(2) 0.0023(17) O3 0.049(2) 0.075(3) 0.118(4) 0.057(3) -0.003(3) 0.021(2) O4 0.247(8) 0.062(3) 0.049(3) -0.017(2) 0.019(4) -0.082(4) O8 0.061(2) 0.060(2) 0.0308(18) -0.0050(17) -0.0158(18) -0.0118(19) O34 0.089(3) 0.035(2) 0.106(4) 0.009(2) 0.053(3) 0.0143(19) O35 0.061(2) 0.047(2) 0.068(3) -0.001(2) 0.028(2) 0.0046(18) N31 0.037(2) 0.0258(17) 0.047(2) -0.0074(19) -0.001(2) 0.0007(15) C5 0.038(2) 0.031(2) 0.056(3) 0.014(2) 0.014(2) 0.004(2) C6 0.0292(19) 0.0244(18) 0.024(2) 0.0038(18) -0.0030(18) -0.0039(17) C7 0.036(2) 0.031(2) 0.033(2) -0.003(2) -0.004(2) -0.0002(19) C9 0.045(3) 0.042(3) 0.052(3) 0.004(3) 0.005(2) -0.018(2) C10 0.051(3) 0.038(3) 0.031(2) 0.013(2) 0.004(2) 0.004(2) C11 0.051(3) 0.046(3) 0.033(2) 0.005(2) 0.007(2) 0.007(2) C12 0.037(2) 0.030(2) 0.040(2) -0.001(2) 0.003(2) 0.0013(19) C13 0.041(2) 0.032(2) 0.031(2) 0.004(2) -0.004(2) 0.006(2) C14 0.066(3) 0.034(3) 0.055(3) 0.006(3) 0.006(3) 0.012(2) C15 0.064(3) 0.063(3) 0.052(3) -0.001(3) -0.031(3) 0.010(3) C32 0.043(2) 0.030(2) 0.032(2) -0.0011(19) 0.006(2) -0.0006(19) C33 0.053(3) 0.038(3) 0.035(2) -0.004(2) 0.009(2) 0.000(2) C36 0.025(2) 0.028(2) 0.043(3) 0.001(2) 0.0044(19) 0.0055(18) C37 0.037(2) 0.036(2) 0.040(3) 0.002(2) 0.007(2) 0.000(2) C38 0.034(2) 0.029(2) 0.063(3) 0.002(2) 0.010(2) -0.0010(19) C39 0.033(2) 0.036(2) 0.067(4) -0.011(3) -0.006(3) 0.000(2) C40 0.044(3) 0.048(3) 0.044(3) 0.001(3) -0.009(3) 0.006(2) C41 0.042(2) 0.028(2) 0.042(3) 0.005(2) -0.002(2) 0.0026(19) _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 S1 O4 1.422(5) . ? S1 O2 1.430(4) . ? S1 O3 1.441(4) . ? S1 C5 1.760(5) . ? O8 C7 1.218(6) . ? O34 C33 1.181(7) . ? O35 C33 1.306(6) . ? N31 C32 1.498(6) . ? C5 C6 1.525(6) . ? C6 C7 1.515(6) . ? C6 C12 1.551(6) . ? C6 C13 1.566(6) . ? C7 C9 1.502(7) . ? C9 C10 1.520(8) . ? C10 C11 1.537(7) . ? C10 C13 1.553(7) . ? C11 C12 1.543(6) . ? C13 C14 1.516(7) . ? C13 C15 1.522(7) . ? C32 C36 1.499(7) . ? C32 C33 1.532(7) . ? C36 C41 1.391(7) . ? C36 C37 1.391(7) . ? C37 C38 1.379(7) . ? C38 C39 1.368(8) . ? C39 C40 1.393(8) . ? C40 C41 1.374(7) . ? 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 O4 S1 O2 116.4(3) . . ? O4 S1 O3 107.0(4) . . ? O2 S1 O3 111.0(3) . . ? O4 S1 C5 109.2(3) . . ? O2 S1 C5 105.8(2) . . ? O3 S1 C5 107.1(3) . . ? C6 C5 S1 121.4(3) . . ? C7 C6 C5 114.8(4) . . ? C7 C6 C12 103.3(3) . . ? C5 C6 C12 119.7(4) . . ? C7 C6 C13 99.1(3) . . ? C5 C6 C13 114.6(4) . . ? C12 C6 C13 102.6(3) . . ? O8 C7 C9 125.6(5) . . ? O8 C7 C6 126.8(4) . . ? C9 C7 C6 107.6(4) . . ? C7 C9 C10 101.6(4) . . ? C9 C10 C11 106.5(4) . . ? C9 C10 C13 103.0(4) . . ? C11 C10 C13 103.2(4) . . ? C10 C11 C12 102.5(4) . . ? C11 C12 C6 104.5(4) . . ? C14 C13 C15 108.1(4) . . ? C14 C13 C10 114.8(4) . . ? C15 C13 C10 113.4(4) . . ? C14 C13 C6 113.1(4) . . ? C15 C13 C6 113.8(4) . . ? C10 C13 C6 93.1(3) . . ? N31 C32 C36 112.5(4) . . ? N31 C32 C33 107.8(4) . . ? C36 C32 C33 112.0(4) . . ? O34 C33 O35 126.1(5) . . ? O34 C33 C32 123.6(5) . . ? O35 C33 C32 110.4(4) . . ? C41 C36 C37 119.0(5) . . ? C41 C36 C32 121.1(4) . . ? C37 C36 C32 119.9(4) . . ? C38 C37 C36 120.4(5) . . ? C39 C38 C37 120.4(5) . . ? C38 C39 C40 119.7(5) . . ? C41 C40 C39 120.2(5) . . ? C40 C41 C36 120.2(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 59.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.764 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.087 data_LPG-dCS _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-phenylglycine(1S)-(+)-camphor-10-sulfonate ; _chemical_name_common L-PGd-CS _chemical_melting_point 191 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 N O6 S' _chemical_formula_weight 383.45 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' 'O' 'O' 0.0492 0.0322 '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' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 24.943(1) _cell_length_b 7.053(2) _cell_length_c 11.366(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.39(3) _cell_angle_gamma 90.00 _cell_volume 1945.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.769 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 1577 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.2798 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 60.02 _reflns_number_total 1577 _reflns_number_gt 1451 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] 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 noref _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 0.04(4) _refine_ls_number_reflns 1577 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1510 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.003 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 S1 S -0.15935(5) 0.0038(2) -0.25409(9) 0.0469(4) Uani 1 1 d . . . O2 O -0.12062(16) 0.1590(6) -0.2391(3) 0.0518(11) Uani 1 1 d . . . O3 O -0.1326(2) -0.1764(7) -0.2169(4) 0.0716(14) Uani 1 1 d . . . O4 O -0.20354(17) 0.0468(9) -0.1931(4) 0.0792(17) Uani 1 1 d . . . O8 O -0.24810(16) -0.0241(12) -0.6527(3) 0.0841(16) Uani 1 1 d . . . O34 O -0.23939(17) 0.5978(9) -0.0274(4) 0.0752(15) Uani 1 1 d . . . O35 O -0.20210(13) 0.4575(6) 0.1475(3) 0.0508(10) Uani 1 1 d . . . N31 N -0.16515(15) 0.4675(7) -0.1426(3) 0.0409(10) Uani 1 1 d . . . C5 C -0.19324(18) -0.0102(10) -0.4094(4) 0.0476(12) Uani 1 1 d . . . C6 C -0.16081(17) 0.0197(8) -0.5060(4) 0.0396(11) Uani 1 1 d . . . C7 C -0.1986(2) -0.0162(11) -0.6314(4) 0.0541(14) Uani 1 1 d . . . C9 C -0.1621(3) -0.0335(12) -0.7198(4) 0.0657(17) Uani 1 1 d . . . C10 C -0.1049(2) -0.0071(11) -0.6386(4) 0.0547(13) Uani 1 1 d . . . C11 C -0.1011(3) 0.2025(11) -0.6063(5) 0.0591(16) Uani 1 1 d . . . C12 C -0.1409(3) 0.2247(8) -0.5218(5) 0.0527(14) Uani 1 1 d . . . C13 C -0.1103(2) -0.1016(8) -0.5168(5) 0.0485(13) Uani 1 1 d . . . C14 C -0.1224(4) -0.3127(11) -0.5267(8) 0.087(2) Uani 1 1 d . . . C15 C -0.0584(2) -0.0685(12) -0.4153(5) 0.0646(18) Uani 1 1 d . . . C32 C -0.15961(19) 0.4063(8) -0.0139(4) 0.0399(11) Uani 1 1 d . . . C33 C -0.20466(18) 0.5015(9) 0.0325(4) 0.0423(10) Uani 1 1 d . . . C36 C -0.1016(2) 0.4398(9) 0.0575(4) 0.0475(14) Uani 1 1 d . . . C37 C -0.0663(3) 0.2876(12) 0.0935(6) 0.0654(18) Uani 1 1 d . . . C38 C -0.0121(4) 0.320(2) 0.1528(8) 0.098(4) Uani 1 1 d . . . C39 C 0.0051(3) 0.502(3) 0.1836(7) 0.109(4) Uani 1 1 d . . . C40 C -0.0289(4) 0.648(2) 0.1514(10) 0.113(4) Uani 1 1 d . . . C41 C -0.0836(3) 0.6231(13) 0.0870(8) 0.076(2) Uani 1 1 d . . . H16 H -0.2217 0.0820 -0.4230 0.057 Uiso 1 1 d . . . H17 H -0.2091 -0.1334 -0.4221 0.057 Uiso 1 1 d . . . H18 H -0.1658 -0.1548 -0.7574 0.079 Uiso 1 1 d . . . H19 H -0.1701 0.0621 -0.7801 0.079 Uiso 1 1 d . . . H20 H -0.0755 -0.0541 -0.6707 0.065 Uiso 1 1 d . . . H21 H -0.1126 0.2787 -0.6766 0.071 Uiso 1 1 d . . . H22 H -0.0646 0.2361 -0.5659 0.071 Uiso 1 1 d . . . H23 H -0.1223 0.2763 -0.4462 0.063 Uiso 1 1 d . . . H24 H -0.1710 0.3040 -0.5576 0.063 Uiso 1 1 d . . . H25 H -0.1302 -0.3566 -0.4534 0.104 Uiso 1 1 d . . . H26 H -0.1534 -0.3348 -0.5917 0.104 Uiso 1 1 d . . . H27 H -0.0914 -0.3782 -0.5412 0.104 Uiso 1 1 d . . . H28 H -0.0655 -0.1066 -0.3401 0.077 Uiso 1 1 d . . . H29 H -0.0287 -0.1411 -0.4310 0.077 Uiso 1 1 d . . . H30 H -0.0490 0.0621 -0.4120 0.077 Uiso 1 1 d . . . H42 H -0.2031 0.4800 -0.1811 0.049 Uiso 1 1 d . . . H43 H -0.1487 0.3749 -0.1840 0.049 Uiso 1 1 d . . . H44 H -0.1471 0.5856 -0.1441 0.049 Uiso 1 1 d . . . H45 H -0.1662 0.2734 -0.0144 0.048 Uiso 1 1 d . . . H46 H -0.2383 0.4266 0.1543 0.079 Uiso 1 1 d . . . H47 H -0.0793 0.1612 0.0775 0.079 Uiso 1 1 d . . . H48 H 0.0131 0.2173 0.1720 0.118 Uiso 1 1 d . . . H49 H 0.0417 0.5237 0.2284 0.131 Uiso 1 1 d . . . H50 H -0.0157 0.7731 0.1725 0.136 Uiso 1 1 d . . . H51 H -0.1075 0.7283 0.0643 0.092 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 S1 0.0516(7) 0.0642(8) 0.0278(6) -0.0049(6) 0.0152(4) -0.0118(7) O2 0.051(2) 0.070(3) 0.038(2) -0.0146(18) 0.0190(17) -0.012(2) O3 0.100(3) 0.069(3) 0.040(2) 0.016(2) 0.004(2) -0.007(3) O4 0.069(2) 0.122(5) 0.059(2) -0.031(3) 0.0400(19) -0.034(3) O8 0.056(2) 0.143(5) 0.042(2) 0.001(3) -0.0107(16) -0.017(3) O34 0.072(3) 0.110(4) 0.048(2) 0.024(3) 0.0244(19) 0.040(3) O35 0.0465(17) 0.079(3) 0.0283(15) 0.0034(18) 0.0104(13) 0.0069(19) N31 0.0438(19) 0.057(3) 0.0209(16) 0.0017(19) 0.0057(14) 0.0027(19) C5 0.041(2) 0.070(3) 0.031(2) -0.002(3) 0.0062(17) -0.009(3) C6 0.038(2) 0.053(3) 0.025(2) -0.002(2) 0.0023(17) -0.002(2) C7 0.056(3) 0.076(4) 0.025(2) 0.000(3) -0.0032(19) -0.007(3) C9 0.085(4) 0.087(5) 0.024(2) -0.007(3) 0.010(2) -0.005(4) C10 0.064(3) 0.074(4) 0.030(2) -0.005(3) 0.018(2) 0.008(4) C11 0.072(4) 0.075(4) 0.033(3) 0.010(3) 0.016(3) -0.009(3) C12 0.073(4) 0.046(3) 0.042(3) 0.000(3) 0.020(3) -0.002(3) C13 0.055(3) 0.052(3) 0.038(3) 0.001(2) 0.011(2) 0.008(3) C14 0.130(7) 0.061(5) 0.074(5) 0.007(4) 0.035(5) 0.019(5) C15 0.048(3) 0.105(5) 0.041(3) 0.010(3) 0.012(2) 0.015(3) C32 0.045(2) 0.054(3) 0.021(2) 0.002(2) 0.0069(17) 0.003(2) C33 0.041(2) 0.057(3) 0.028(2) 0.004(3) 0.0047(17) 0.010(3) C36 0.040(3) 0.081(4) 0.020(2) -0.003(3) 0.0044(19) 0.003(3) C37 0.055(4) 0.093(5) 0.047(3) 0.011(4) 0.009(3) 0.017(4) C38 0.058(5) 0.185(12) 0.050(4) 0.029(6) 0.008(4) 0.051(7) C39 0.048(4) 0.207(13) 0.064(4) -0.040(8) -0.007(3) -0.006(8) C40 0.054(5) 0.166(11) 0.108(7) -0.072(8) -0.004(4) -0.016(6) C41 0.056(4) 0.094(6) 0.070(4) -0.041(5) -0.003(3) 0.005(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 S1 O2 1.444(4) . ? S1 O3 1.452(5) . ? S1 O4 1.463(4) . ? S1 C5 1.775(4) . ? O8 C7 1.204(6) . ? O34 C33 1.184(6) . ? O35 C33 1.330(6) . ? N31 C32 1.500(5) . ? C5 C6 1.522(6) . ? C6 C7 1.536(6) . ? C6 C13 1.552(7) . ? C6 C12 1.553(8) . ? C7 C9 1.509(7) . ? C9 C10 1.520(8) . ? C10 C11 1.521(11) . ? C10 C13 1.570(8) . ? C11 C12 1.539(8) . ? C13 C14 1.518(10) . ? C13 C15 1.538(8) . ? C32 C36 1.504(7) . ? C32 C33 1.506(7) . ? C36 C41 1.385(11) . ? C36 C37 1.389(10) . ? C37 C38 1.384(12) . ? C38 C39 1.372(19) . ? C39 C40 1.332(19) . ? C40 C41 1.403(11) . ? 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 O2 S1 O3 112.3(3) . . ? O2 S1 O4 110.1(3) . . ? O3 S1 O4 112.9(3) . . ? O2 S1 C5 108.1(3) . . ? O3 S1 C5 108.7(3) . . ? O4 S1 C5 104.2(2) . . ? C6 C5 S1 120.0(3) . . ? C5 C6 C7 109.4(4) . . ? C5 C6 C13 123.9(4) . . ? C7 C6 C13 99.9(4) . . ? C5 C6 C12 116.8(5) . . ? C7 C6 C12 101.0(5) . . ? C13 C6 C12 102.5(4) . . ? O8 C7 C9 127.7(4) . . ? O8 C7 C6 125.1(5) . . ? C9 C7 C6 107.2(4) . . ? C7 C9 C10 102.2(4) . . ? C9 C10 C11 105.2(6) . . ? C9 C10 C13 102.9(5) . . ? C11 C10 C13 102.3(4) . . ? C10 C11 C12 103.7(5) . . ? C11 C12 C6 104.3(5) . . ? C14 C13 C15 108.9(6) . . ? C14 C13 C6 113.2(6) . . ? C15 C13 C6 114.5(5) . . ? C14 C13 C10 114.0(6) . . ? C15 C13 C10 111.6(5) . . ? C6 C13 C10 94.1(4) . . ? N31 C32 C36 109.9(4) . . ? N31 C32 C33 107.8(4) . . ? C36 C32 C33 116.3(4) . . ? O34 C33 O35 124.1(4) . . ? O34 C33 C32 124.1(4) . . ? O35 C33 C32 111.7(4) . . ? C41 C36 C37 120.1(5) . . ? C41 C36 C32 119.7(5) . . ? C37 C36 C32 120.2(6) . . ? C38 C37 C36 119.8(9) . . ? C39 C38 C37 119.5(8) . . ? C40 C39 C38 120.9(7) . . ? C39 C40 C41 121.7(11) . . ? C36 C41 C40 117.9(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 60.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.307 _refine_diff_density_min -0.732 _refine_diff_density_rms 0.087 data_LPG-HCl _audit_creation_method SHELXL-97 _chemical_name_systematic ; L-enylglycine hydrochloride ; _chemical_name_common L-PGHCl _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Cl N O2' _chemical_formula_weight 187.62 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' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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' _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 7.261(1) _cell_length_b 22.781(2) _cell_length_c 5.438(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 899.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 3.445 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 2817 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 64.99 _reflns_number_total 1539 _reflns_number_gt 1516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.045(3) _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 0.013(16) _refine_ls_number_reflns 1539 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl -0.66671(5) -0.185610(17) -0.77243(9) 0.0392(2) Uani 1 1 d . . . O1 O -0.6682(2) -0.30339(6) -0.3748(2) 0.0441(4) Uani 1 1 d . . . O2 O -0.88115(19) -0.34362(7) -0.6198(3) 0.0552(4) Uani 1 1 d . . . N1 N -0.4130(2) -0.30231(7) -0.7388(3) 0.0369(4) Uani 1 1 d . . . C1 C -0.5819(2) -0.33899(7) -0.7745(3) 0.0315(4) Uani 1 1 d . . . C2 C -0.7133(3) -0.32591(6) -0.5643(3) 0.0331(4) Uani 1 1 d . . . C3 C -0.5380(2) -0.40406(7) -0.7799(3) 0.0297(4) Uani 1 1 d . . . C4 C -0.4447(3) -0.43115(7) -0.5884(3) 0.0362(4) Uani 1 1 d . . . C5 C -0.4205(2) -0.49160(7) -0.5899(4) 0.0401(4) Uani 1 1 d . . . C6 C -0.4890(2) -0.52480(7) -0.7810(4) 0.0406(5) Uani 1 1 d . . . C7 C -0.5816(3) -0.49821(7) -0.9729(4) 0.0429(5) Uani 1 1 d . . . C8 C -0.6062(3) -0.43774(8) -0.9721(3) 0.0364(4) Uani 1 1 d . . . H1 H -0.4466 -0.2620 -0.7341 0.044 Uiso 1 1 d . . . H2 H -0.3552 -0.3128 -0.5884 0.044 Uiso 1 1 d . . . H3 H -0.3302 -0.3088 -0.8712 0.044 Uiso 1 1 d . . . H4 H -0.6389 -0.3283 -0.9252 0.038 Uiso 1 1 d . . . H5 H -0.9510 -0.3364 -0.5046 0.060 Uiso 1 1 d . . . H6 H -0.3974 -0.4084 -0.4564 0.043 Uiso 1 1 d . . . H7 H -0.3566 -0.5102 -0.4587 0.048 Uiso 1 1 d . . . H8 H -0.4725 -0.5662 -0.7809 0.049 Uiso 1 1 d . . . H9 H -0.6282 -0.5212 -1.1047 0.051 Uiso 1 1 d . . . H10 H -0.6701 -0.4194 -1.1038 0.044 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 Cl1 0.0411(3) 0.0385(3) 0.0380(3) -0.00241(15) -0.00968(19) 0.00144(15) O1 0.0493(8) 0.0510(7) 0.0318(7) -0.0063(6) 0.0061(6) 0.0012(6) O2 0.0379(7) 0.0702(9) 0.0574(9) -0.0208(8) 0.0113(7) -0.0054(7) N1 0.0434(8) 0.0309(6) 0.0363(8) -0.0028(6) 0.0095(8) -0.0062(6) C1 0.0374(8) 0.0311(8) 0.0260(8) -0.0003(6) 0.0037(8) -0.0017(6) C2 0.0364(8) 0.0301(7) 0.0327(9) 0.0038(7) 0.0055(8) 0.0032(6) C3 0.0298(7) 0.0321(8) 0.0273(9) -0.0017(6) 0.0046(7) -0.0033(6) C4 0.0385(9) 0.0377(8) 0.0324(10) -0.0011(7) -0.0033(8) -0.0045(7) C5 0.0382(9) 0.0380(9) 0.0441(11) 0.0036(8) -0.0043(9) 0.0061(7) C6 0.0383(8) 0.0296(8) 0.0538(12) -0.0057(8) 0.0082(10) 0.0005(6) C7 0.0481(10) 0.0391(8) 0.0415(10) -0.0137(8) 0.0038(9) -0.0088(8) C8 0.0432(9) 0.0390(8) 0.0272(8) -0.0015(7) -0.0010(8) -0.0017(7) _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 C2 1.197(2) . ? O2 C2 1.319(3) . ? N1 C1 1.496(2) . ? C1 C3 1.516(2) . ? C1 C2 1.518(2) . ? C3 C4 1.387(3) . ? C3 C8 1.388(2) . ? C4 C5 1.388(2) . ? C5 C6 1.379(3) . ? C6 C7 1.381(3) . ? C7 C8 1.389(2) . ? 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 N1 C1 C3 112.10(13) . . ? N1 C1 C2 107.91(13) . . ? C3 C1 C2 109.79(13) . . ? O1 C2 O2 125.52(17) . . ? O1 C2 C1 124.08(17) . . ? O2 C2 C1 110.39(15) . . ? C4 C3 C8 119.58(16) . . ? C4 C3 C1 121.53(16) . . ? C8 C3 C1 118.68(16) . . ? C3 C4 C5 119.92(17) . . ? C6 C5 C4 120.20(18) . . ? C5 C6 C7 120.31(15) . . ? C6 C7 C8 119.70(17) . . ? C3 C8 C7 120.29(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.187 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.043