# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _audit_creation_date 15/12/2003 _audit_update_record 16/12/2003 _publ_section_title ; The same and not the same. Similarities and differences in the resolution of trans-chrysanthemic acid of industrial origin by the enantiomers of some threo-1-aryl-2-dimethylamino-1,3-propanediols. ; _publ_contact_author_email mazzand@ms.fci.unibo.it _publ_contact_author_fax '[039]051 209 3654' _publ_contact_author_phone '[039]051 209 3633' _publ_contact_author_name 'Goffredo Rosini' _publ_author_address 'Viale Risorgimento 4 - 40136 Bologna' _publ_contact_author ; Dr. Andrea Mazzanti Universita di Bologna Dipartimento di Chimica Organica A.Mangini Viale Risorgimento 4 40136 Bologna Italy ; loop_ _publ_author_name G.Rosini C.Ayoub V.Borzatta E.Marotta A.Mazzanti P.Righi data_ortho _database_code_depnum_ccdc_archive 'CCDC 626016' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R,2R)-1,3-dihydroxy-N,N-dimethyl-1-[4-(methylthio)phenyl]propan- 2-aminium (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)- cyclopropanecarboxylate, methanol solvated ; _chemical_name_common ; (1R,2R)-1,3-dihydroxy-N,N-dimethyl-1-(4- (methylthio)phenyl)propan-2-aminium (1R,3R)-2,2-dimethyl-3-(2- methylprop-1-enyl)-cyclopropanecarboxylate, methanol solvated ; _chemical_melting_point '138-140 C' _chemical_formula_moiety 'C12 H20 N O2 S, C10 H15 O2, C H4 O' _chemical_formula_sum 'C23 H39 N O5 S' _chemical_formula_weight 441.61 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' S S 0.1246 0.1234 '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 21 21 21' 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 7.1563(10) _cell_length_b 13.1156(15) _cell_length_c 27.469(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2578.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 315 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 29.28 _exptl_crystal_description brick _exptl_crystal_colour white _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8856 _exptl_absorpt_correction_T_max 0.9263 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33557 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 30.02 _reflns_number_total 7508 _reflns_number_gt 6443 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart V5.051, Bruker 1998' _computing_cell_refinement 'Smart V5.051, Bruker 1998' _computing_data_reduction 'Saint+ 5.02, Bruker 1998' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.2.1, CCDC' _computing_publication_material 'Mercury 1.2.1, CCDC' _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^)+(0.0857P)^2^+0.3050P] 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 0.02(8) _chemical_absolute_configuration rm _refine_ls_number_reflns 7508 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _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 S1 S 0.52043(8) -0.16495(5) 0.94169(2) 0.06817(16) Uani 1 1 d . . . O1 O 0.47400(19) 0.51288(10) 0.78383(4) 0.0517(3) Uani 1 1 d . . . O2 O 0.2404(2) 0.41139(11) 0.80266(5) 0.0567(3) Uani 1 1 d . . . O3 O -0.19054(19) -0.06294(10) 0.79228(5) 0.0492(3) Uani 1 1 d . . . H30 H -0.2091 -0.0767 0.7636 0.074 Uiso 1 1 calc R . . O4 O -0.0389(2) 0.28374(10) 0.83047(6) 0.0632(4) Uani 1 1 d . . . H4 H 0.0383 0.3292 0.8266 0.095 Uiso 1 1 calc R . . N1 N -0.26171(19) 0.14129(11) 0.77358(5) 0.0405(3) Uani 1 1 d . . . HN1 H -0.321(3) 0.0849(18) 0.7630(8) 0.049 Uiso 1 1 d . . . C1 C 0.3924(2) 0.45374(11) 0.81272(5) 0.0391(3) Uani 1 1 d . . . C2 C 0.4837(3) 0.43483(12) 0.86070(5) 0.0444(3) Uani 1 1 d . . . H2 H 0.6201 0.4413 0.8602 0.053 Uiso 1 1 calc R . . C3 C 0.4112(3) 0.35576(13) 0.89610(6) 0.0502(4) Uani 1 1 d . . . H3 H 0.2944 0.3226 0.8864 0.060 Uiso 1 1 calc R . . C4 C 0.3938(4) 0.46797(14) 0.90825(6) 0.0576(5) Uani 1 1 d . . . C5 C 0.5497(4) 0.28763(15) 0.91986(8) 0.0669(6) Uani 1 1 d . . . H5 H 0.6742 0.3078 0.9190 0.080 Uiso 1 1 calc R . . C6 C 0.5113(5) 0.20019(16) 0.94233(7) 0.0800(8) Uani 1 1 d . . . C7 C 0.6741(8) 0.1368(2) 0.96269(14) 0.1243(17) Uani 1 1 d . . . H7A H 0.6261 0.0757 0.9774 0.186 Uiso 1 1 calc R . . H7B H 0.7400 0.1759 0.9867 0.186 Uiso 1 1 calc R . . H7C H 0.7578 0.1191 0.9367 0.186 Uiso 1 1 calc R . . C8 C 0.3172(7) 0.1597(2) 0.94818(12) 0.1092(13) Uani 1 1 d . . . H8A H 0.3215 0.0954 0.9648 0.164 Uiso 1 1 calc R . . H8B H 0.2615 0.1505 0.9167 0.164 Uiso 1 1 calc R . . H8C H 0.2440 0.2071 0.9667 0.164 Uiso 1 1 calc R . . C9 C 0.5236(6) 0.51182(18) 0.94619(8) 0.0898(10) Uani 1 1 d . . . H9A H 0.4970 0.5830 0.9505 0.135 Uiso 1 1 calc R . . H9B H 0.6507 0.5037 0.9357 0.135 Uiso 1 1 calc R . . H9C H 0.5057 0.4767 0.9765 0.135 Uiso 1 1 calc R . . C10 C 0.2047(5) 0.5151(2) 0.90699(10) 0.0858(8) Uani 1 1 d . . . H10A H 0.2139 0.5859 0.9156 0.129 Uiso 1 1 calc R . . H10B H 0.1245 0.4809 0.9297 0.129 Uiso 1 1 calc R . . H10C H 0.1536 0.5090 0.8748 0.129 Uiso 1 1 calc R . . C11 C -0.1138(2) 0.11025(12) 0.81054(6) 0.0395(3) Uani 1 1 d . . . H11 H -0.1754 0.1031 0.8422 0.047 Uiso 1 1 calc R . . C12 C -0.0380(2) 0.00518(11) 0.79598(5) 0.0382(3) Uani 1 1 d . . . H12 H 0.0239 0.0104 0.7643 0.046 Uiso 1 1 calc R . . C13 C 0.0387(2) 0.18959(13) 0.81580(8) 0.0498(4) Uani 1 1 d . . . H13A H 0.1292 0.1670 0.8398 0.060 Uiso 1 1 calc R . . H13B H 0.1029 0.1980 0.7850 0.060 Uiso 1 1 calc R . . C14 C 0.0994(2) -0.03581(11) 0.83307(5) 0.0379(3) Uani 1 1 d . . . C15 C 0.2877(2) -0.04560(13) 0.82253(6) 0.0442(3) Uani 1 1 d . . . H15 H 0.3316 -0.0254 0.7922 0.053 Uiso 1 1 calc R . . C16 C 0.4123(3) -0.08489(14) 0.85637(7) 0.0489(4) Uani 1 1 d . . . H16 H 0.5385 -0.0902 0.8487 0.059 Uiso 1 1 calc R . . C17 C 0.3489(3) -0.11632(13) 0.90167(6) 0.0450(3) Uani 1 1 d . . . C18 C 0.1604(3) -0.10793(15) 0.91262(7) 0.0497(4) Uani 1 1 d . . . H18 H 0.1165 -0.1294 0.9428 0.060 Uiso 1 1 calc R . . C19 C 0.0362(2) -0.06750(14) 0.87858(6) 0.0472(3) Uani 1 1 d . . . H19 H -0.0899 -0.0616 0.8863 0.057 Uiso 1 1 calc R . . C20 C 0.4059(5) -0.1730(3) 0.99811(10) 0.1020(11) Uani 1 1 d . . . H20A H 0.4905 -0.1994 1.0221 0.153 Uiso 1 1 calc R . . H20B H 0.3001 -0.2176 0.9953 0.153 Uiso 1 1 calc R . . H20C H 0.3645 -0.1064 1.0078 0.153 Uiso 1 1 calc R . . C21 C -0.4168(3) 0.20168(17) 0.79602(10) 0.0639(5) Uani 1 1 d . . . H21A H -0.4615 0.1671 0.8245 0.096 Uiso 1 1 calc R . . H21B H -0.5170 0.2087 0.7730 0.096 Uiso 1 1 calc R . . H21C H -0.3714 0.2680 0.8049 0.096 Uiso 1 1 calc R . . C22 C -0.1886(3) 0.19196(18) 0.72934(8) 0.0608(5) Uani 1 1 d . . . H22A H -0.0894 0.1517 0.7158 0.091 Uiso 1 1 calc R . . H22B H -0.1419 0.2583 0.7377 0.091 Uiso 1 1 calc R . . H22C H -0.2872 0.1987 0.7059 0.091 Uiso 1 1 calc R . . C23 C 0.2411(5) 0.1811(2) 0.65751(13) 0.0913(9) Uani 1 1 d . . . H23A H 0.2049 0.2493 0.6660 0.137 Uiso 1 1 calc R . . H23B H 0.1654 0.1574 0.6310 0.137 Uiso 1 1 calc R . . H23C H 0.3702 0.1806 0.6480 0.137 Uiso 1 1 calc R . . O24 O 0.2169(3) 0.1186(2) 0.69674(10) 0.1174(10) Uani 1 1 d . . . H24 H 0.2914 0.0712 0.6953 0.141 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 S1 0.0605(3) 0.0781(3) 0.0658(3) 0.0122(2) -0.0096(2) 0.0204(3) O1 0.0530(7) 0.0588(7) 0.0433(6) 0.0133(5) -0.0046(5) -0.0143(6) O2 0.0548(7) 0.0656(7) 0.0498(7) 0.0149(6) -0.0120(6) -0.0229(6) O3 0.0547(7) 0.0462(6) 0.0468(6) 0.0023(5) -0.0109(5) -0.0143(5) O4 0.0539(7) 0.0445(6) 0.0914(10) -0.0118(7) 0.0081(7) -0.0154(6) N1 0.0343(6) 0.0402(6) 0.0471(7) -0.0037(5) 0.0012(5) 0.0005(5) C1 0.0460(8) 0.0345(6) 0.0369(6) 0.0033(5) -0.0024(6) -0.0024(6) C2 0.0537(9) 0.0413(7) 0.0383(7) 0.0068(6) -0.0086(7) -0.0080(7) C3 0.0692(11) 0.0413(7) 0.0402(7) 0.0063(6) -0.0067(8) -0.0093(8) C4 0.0924(15) 0.0436(8) 0.0369(7) 0.0023(6) -0.0010(8) -0.0016(9) C5 0.0998(17) 0.0487(9) 0.0521(10) 0.0108(8) -0.0219(11) -0.0048(11) C6 0.152(3) 0.0430(9) 0.0448(9) 0.0046(7) -0.0119(14) 0.0035(13) C7 0.209(5) 0.0661(16) 0.098(2) 0.0183(15) -0.041(3) 0.031(2) C8 0.187(4) 0.0616(14) 0.0788(18) 0.0111(13) 0.020(2) -0.035(2) C9 0.163(3) 0.0592(11) 0.0472(10) -0.0028(9) -0.0225(15) -0.0228(16) C10 0.114(2) 0.0815(16) 0.0625(13) 0.0033(12) 0.0216(14) 0.0259(16) C11 0.0371(7) 0.0419(7) 0.0396(7) 0.0004(5) 0.0007(6) -0.0060(6) C12 0.0411(7) 0.0383(7) 0.0351(6) 0.0017(5) 0.0010(5) -0.0037(6) C13 0.0387(7) 0.0449(8) 0.0657(10) -0.0028(7) -0.0016(7) -0.0095(6) C14 0.0387(7) 0.0368(7) 0.0382(7) 0.0012(5) 0.0011(5) -0.0027(5) C15 0.0427(8) 0.0469(8) 0.0429(7) 0.0024(6) 0.0073(6) -0.0003(6) C16 0.0400(7) 0.0518(9) 0.0550(9) 0.0018(7) 0.0055(7) 0.0032(7) C17 0.0476(8) 0.0407(7) 0.0468(8) 0.0023(6) -0.0048(7) 0.0022(6) C18 0.0507(9) 0.0547(9) 0.0437(8) 0.0109(7) 0.0035(7) -0.0015(7) C19 0.0383(7) 0.0594(9) 0.0438(7) 0.0088(7) 0.0052(6) -0.0033(7) C20 0.0797(17) 0.167(3) 0.0590(13) 0.0212(18) -0.0106(12) 0.029(2) C21 0.0408(8) 0.0647(11) 0.0861(14) -0.0258(11) 0.0029(9) 0.0087(8) C22 0.0587(11) 0.0639(12) 0.0597(11) 0.0209(9) -0.0005(9) 0.0042(9) C23 0.099(2) 0.0785(16) 0.096(2) 0.0251(15) 0.0222(16) 0.0225(16) O24 0.0890(14) 0.143(2) 0.1202(18) 0.0643(16) 0.0499(13) 0.0664(15) _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 C20 1.756(3) . ? S1 C17 1.7668(18) . ? O1 C1 1.2539(19) . ? O2 C1 1.252(2) . ? O3 C12 1.4141(19) . ? O4 C13 1.413(2) . ? N1 C22 1.481(2) . ? N1 C21 1.496(2) . ? N1 C11 1.522(2) . ? C1 C2 1.492(2) . ? C2 C3 1.513(2) . ? C2 C4 1.519(3) . ? C3 C5 1.485(3) . ? C3 C4 1.514(3) . ? C4 C10 1.489(4) . ? C4 C9 1.510(3) . ? C5 C6 1.331(3) . ? C6 C8 1.496(6) . ? C6 C7 1.537(5) . ? C11 C13 1.515(2) . ? C11 C12 1.534(2) . ? C12 C14 1.514(2) . ? C14 C15 1.384(2) . ? C14 C19 1.393(2) . ? C15 C16 1.387(3) . ? C16 C17 1.387(3) . ? C17 C18 1.387(3) . ? C18 C19 1.395(3) . ? C23 O24 1.365(4) . ? 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 C20 S1 C17 104.28(12) . . ? C22 N1 C21 111.26(17) . . ? C22 N1 C11 114.95(14) . . ? C21 N1 C11 112.50(15) . . ? O2 C1 O1 122.62(15) . . ? O2 C1 C2 120.12(14) . . ? O1 C1 C2 117.27(14) . . ? C1 C2 C3 122.11(15) . . ? C1 C2 C4 121.77(16) . . ? C3 C2 C4 59.91(11) . . ? C5 C3 C2 117.79(19) . . ? C5 C3 C4 122.87(17) . . ? C2 C3 C4 60.25(11) . . ? C10 C4 C9 114.7(2) . . ? C10 C4 C3 118.3(2) . . ? C9 C4 C3 118.1(2) . . ? C10 C4 C2 118.93(18) . . ? C9 C4 C2 116.2(2) . . ? C3 C4 C2 59.84(11) . . ? C6 C5 C3 125.8(3) . . ? C5 C6 C8 123.2(3) . . ? C5 C6 C7 118.6(3) . . ? C8 C6 C7 118.2(3) . . ? C13 C11 N1 112.39(13) . . ? C13 C11 C12 112.77(13) . . ? N1 C11 C12 108.20(12) . . ? O3 C12 C14 108.98(12) . . ? O3 C12 C11 108.26(13) . . ? C14 C12 C11 111.91(12) . . ? O4 C13 C11 110.12(14) . . ? C15 C14 C19 118.41(15) . . ? C15 C14 C12 121.62(14) . . ? C19 C14 C12 119.94(14) . . ? C14 C15 C16 121.34(15) . . ? C17 C16 C15 120.09(16) . . ? C18 C17 C16 119.27(16) . . ? C18 C17 S1 124.72(14) . . ? C16 C17 S1 116.01(14) . . ? C17 C18 C19 120.32(16) . . ? C14 C19 C18 120.55(16) . . ? 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 O2 C1 C2 C3 7.5(3) . . . . ? O1 C1 C2 C3 -172.60(17) . . . . ? O2 C1 C2 C4 -64.6(2) . . . . ? O1 C1 C2 C4 115.31(19) . . . . ? C1 C2 C3 C5 135.29(18) . . . . ? C4 C2 C3 C5 -113.9(2) . . . . ? C1 C2 C3 C4 -110.8(2) . . . . ? C5 C3 C4 C10 -145.5(2) . . . . ? C2 C3 C4 C10 108.8(2) . . . . ? C5 C3 C4 C9 0.1(3) . . . . ? C2 C3 C4 C9 -105.6(2) . . . . ? C5 C3 C4 C2 105.7(2) . . . . ? C1 C2 C4 C10 3.6(3) . . . . ? C3 C2 C4 C10 -107.7(2) . . . . ? C1 C2 C4 C9 -139.89(18) . . . . ? C3 C2 C4 C9 108.8(2) . . . . ? C1 C2 C4 C3 111.33(18) . . . . ? C2 C3 C5 C6 -163.1(2) . . . . ? C4 C3 C5 C6 126.0(2) . . . . ? C3 C5 C6 C8 -2.1(4) . . . . ? C3 C5 C6 C7 177.0(2) . . . . ? C22 N1 C11 C13 39.7(2) . . . . ? C21 N1 C11 C13 -89.05(18) . . . . ? C22 N1 C11 C12 -85.50(17) . . . . ? C21 N1 C11 C12 145.78(15) . . . . ? C13 C11 C12 O3 179.74(13) . . . . ? N1 C11 C12 O3 -55.31(15) . . . . ? C13 C11 C12 C14 59.63(17) . . . . ? N1 C11 C12 C14 -175.42(12) . . . . ? N1 C11 C13 O4 58.9(2) . . . . ? C12 C11 C13 O4 -178.43(14) . . . . ? O3 C12 C14 C15 129.04(16) . . . . ? C11 C12 C14 C15 -111.26(17) . . . . ? O3 C12 C14 C19 -49.1(2) . . . . ? C11 C12 C14 C19 70.61(18) . . . . ? C19 C14 C15 C16 -0.7(3) . . . . ? C12 C14 C15 C16 -178.84(15) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C15 C16 C17 S1 -179.98(14) . . . . ? C20 S1 C17 C18 -11.3(2) . . . . ? C20 S1 C17 C16 168.63(19) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? S1 C17 C18 C19 179.39(15) . . . . ? C15 C14 C19 C18 0.1(3) . . . . ? C12 C14 C19 C18 178.28(16) . . . . ? C17 C18 C19 C14 0.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H30 O2 0.82 1.84 2.6534(18) 171.8 3_546 N1 HN1 O1 0.90(2) 1.94(2) 2.7626(19) 152(2) 3_546 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.412 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.043 # Attachment 'unsolvated-rev.CIF' data_p21 _database_code_depnum_ccdc_archive 'CCDC 626017' _audit_creation_date 23/01/2004 _audit_update_record 21/12/2006 _publ_section_references ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R,2R)-1,3-dihydroxy-N,N-dimethyl-1-[4-(methylthio)phenyl]propan- 2-aminium (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)- cyclopropanecarboxylate ; _chemical_name_common ; (1R,2R)-1,3-dihydroxy-N,N-dimethyl-1-(4- (methylthio)phenyl)propan-2-aminium (1R,3R)-2,2-dimethyl-3-(2- methylprop-1-enyl)-cyclopropanecarboxylate ; _chemical_melting_point '138-140 C' _chemical_formula_moiety 'C12 H20 N O2 S, C10 H15 O2' _chemical_formula_sum 'C22 H35 N O4 S' _chemical_formula_weight 409.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.9940(5) _cell_length_b 7.8004(4) _cell_length_c 15.8597(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.3010(10) _cell_angle_gamma 90.00 _cell_volume 1186.68(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 142 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.20 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8955 _exptl_absorpt_correction_T_max 0.9532 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10410 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4144 _reflns_number_gt 3822 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart V5.051, Bruker 1998' _computing_cell_refinement 'Smart V5.051, Bruker 1998' _computing_data_reduction 'Saint+ 5.02, Bruker 1998' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.2.1, CCDC' _computing_publication_material 'Mercury 1.2.1, CCDC' _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^)+(0.1006P)^2^+0.1784P] 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 0.071(8) _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 0.10(16) _chemical_absolute_configuration rm _refine_ls_number_reflns 4144 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1548 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 S1 S 0.3750(2) 0.1603(2) 0.10856(15) 0.1720(9) Uani 1 1 d . . . N1 N 0.7727(2) 0.9349(3) 0.43925(13) 0.0501(5) Uani 1 1 d . . . H1N H 0.852(4) 0.905(4) 0.435(2) 0.060 Uiso 1 1 d . . . O1 O 0.95524(18) 1.4281(3) 0.55152(11) 0.0606(5) Uani 1 1 d . . . O2 O 0.77731(18) 1.4735(3) 0.60506(15) 0.0767(7) Uani 1 1 d . . . O3 O 0.84269(16) 0.6113(3) 0.41093(11) 0.0522(4) Uani 1 1 d . . . H31 H 0.8731 0.5502 0.4541 0.078 Uiso 1 1 calc R . . O4 O 0.4783(2) 0.8359(4) 0.43975(16) 0.0838(8) Uani 1 1 d . . . H41 H 0.3974 0.8658 0.4333 0.126 Uiso 1 1 calc R . . C1 C 0.9897(2) 1.3647(3) 0.69997(15) 0.0478(6) Uani 1 1 d . . . H1 H 1.0589 1.2781 0.6963 0.057 Uiso 1 1 calc R . . C2 C 1.0380(3) 1.4904(4) 0.77531(17) 0.0601(7) Uani 1 1 d . . . C3 C 0.9365(3) 1.3506(4) 0.78072(17) 0.0596(7) Uani 1 1 d . . . H3 H 0.8402 1.3891 0.7720 0.072 Uiso 1 1 calc R . . C4 C 0.9780(4) 1.2052(4) 0.84015(19) 0.0674(8) Uani 1 1 d . . . H4 H 1.0626 1.1541 0.8414 0.081 Uiso 1 1 calc R . . C5 C 0.9095(4) 1.1366(4) 0.89284(19) 0.0714(8) Uani 1 1 d . . . C6 C 0.8989(2) 1.4248(4) 0.61331(16) 0.0487(5) Uani 1 1 d . . . C7 C 0.7707(5) 1.1989(6) 0.8972(3) 0.0925(11) Uani 1 1 d . . . H7A H 0.7406 1.1321 0.9394 0.139 Uiso 1 1 calc R . . H7B H 0.7044 1.1876 0.8405 0.139 Uiso 1 1 calc R . . H7C H 0.7777 1.3172 0.9147 0.139 Uiso 1 1 calc R . . C8 C 0.9705(6) 0.9917(6) 0.9531(3) 0.1071(15) Uani 1 1 d . . . H8A H 0.9071 0.9591 0.9859 0.161 Uiso 1 1 calc R . . H8B H 1.0574 1.0272 0.9929 0.161 Uiso 1 1 calc R . . H8C H 0.9862 0.8957 0.9192 0.161 Uiso 1 1 calc R . . C9 C 1.1874(4) 1.4761(6) 0.83050(19) 0.0796(10) Uani 1 1 d . . . H9A H 1.2060 1.5621 0.8756 0.119 Uiso 1 1 calc R . . H9B H 1.2484 1.4925 0.7940 0.119 Uiso 1 1 calc R . . H9C H 1.2030 1.3645 0.8570 0.119 Uiso 1 1 calc R . . C10 C 0.9855(5) 1.6722(5) 0.7637(3) 0.0858(10) Uani 1 1 d . . . H10A H 1.0256 1.7357 0.8166 0.129 Uiso 1 1 calc R . . H10B H 0.8858 1.6726 0.7511 0.129 Uiso 1 1 calc R . . H10C H 1.0118 1.7244 0.7159 0.129 Uiso 1 1 calc R . . C11 C 0.6682(2) 0.8257(3) 0.37436(15) 0.0448(5) Uani 1 1 d . . . H11 H 0.6849 0.8443 0.3171 0.054 Uiso 1 1 calc R . . C12 C 0.6974(2) 0.6344(3) 0.39636(15) 0.0448(5) Uani 1 1 d . . . H12 H 0.6720 0.6063 0.4501 0.054 Uiso 1 1 calc R . . C13 C 0.6165(2) 0.5224(3) 0.32251(16) 0.0478(6) Uani 1 1 d . . . C14 C 0.4938(3) 0.4421(5) 0.3257(2) 0.0758(9) Uani 1 1 d . . . H14 H 0.4601 0.4613 0.3739 0.091 Uiso 1 1 calc R . . C15 C 0.4222(4) 0.3374(6) 0.2613(3) 0.0960(12) Uani 1 1 d . . . H15 H 0.3404 0.2858 0.2655 0.115 Uiso 1 1 calc R . . C16 C 0.4696(4) 0.3062(5) 0.1889(3) 0.0857(11) Uani 1 1 d . . . C17 C 0.5932(4) 0.3835(4) 0.1835(2) 0.0749(9) Uani 1 1 d . . . H17 H 0.6268 0.3641 0.1353 0.090 Uiso 1 1 calc R . . C18 C 0.6642(3) 0.4889(4) 0.25088(18) 0.0593(7) Uani 1 1 d . . . H18 H 0.7471 0.5391 0.2478 0.071 Uiso 1 1 calc R . . C19 C 0.5175(3) 0.8755(4) 0.36385(19) 0.0606(7) Uani 1 1 d . . . H19A H 0.5060 0.9975 0.3522 0.073 Uiso 1 1 calc R . . H19B H 0.4574 0.8149 0.3141 0.073 Uiso 1 1 calc R . . C20 C 0.7601(4) 1.1193(4) 0.4151(2) 0.0770(9) Uani 1 1 d . . . H20A H 0.7565 1.1316 0.3542 0.115 Uiso 1 1 calc R . . H20B H 0.8394 1.1804 0.4506 0.115 Uiso 1 1 calc R . . H20C H 0.6765 1.1650 0.4247 0.115 Uiso 1 1 calc R . . C21 C 0.7801(3) 0.9108(6) 0.53363(17) 0.0733(9) Uani 1 1 d . . . H21A H 0.7880 0.7908 0.5476 0.110 Uiso 1 1 calc R . . H21B H 0.6971 0.9557 0.5445 0.110 Uiso 1 1 calc R . . H21C H 0.8600 0.9703 0.5695 0.110 Uiso 1 1 calc R . . C22 C 0.4376(9) 0.1902(13) 0.0174(6) 0.171(3) Uiso 1 1 d . . . H22A H 0.3902 0.1136 -0.0287 0.256 Uiso 1 1 calc R . . H22B H 0.5358 0.1669 0.0334 0.256 Uiso 1 1 calc R . . H22C H 0.4212 0.3064 -0.0027 0.256 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 S1 0.1570(14) 0.1183(12) 0.2020(18) -0.0740(12) -0.0133(13) -0.0424(10) N1 0.0432(10) 0.0616(12) 0.0502(10) -0.0030(9) 0.0209(8) 0.0040(10) O1 0.0486(9) 0.0888(14) 0.0459(8) 0.0145(9) 0.0157(7) 0.0158(9) O2 0.0351(9) 0.1109(19) 0.0873(13) 0.0311(13) 0.0223(8) 0.0066(11) O3 0.0352(8) 0.0654(11) 0.0579(10) 0.0145(9) 0.0162(7) 0.0066(8) O4 0.0500(11) 0.124(2) 0.0877(14) 0.0182(14) 0.0360(10) 0.0219(12) C1 0.0456(12) 0.0580(14) 0.0446(12) 0.0028(10) 0.0204(10) 0.0040(10) C2 0.0681(17) 0.0692(17) 0.0494(13) -0.0026(13) 0.0272(12) 0.0004(14) C3 0.0606(15) 0.0726(17) 0.0550(14) 0.0055(13) 0.0318(12) 0.0078(13) C4 0.0814(19) 0.0725(18) 0.0564(15) 0.0035(14) 0.0326(14) 0.0080(16) C5 0.107(2) 0.0640(17) 0.0532(14) -0.0049(14) 0.0381(15) -0.0068(17) C6 0.0358(11) 0.0564(13) 0.0550(12) 0.0052(11) 0.0146(9) -0.0043(10) C7 0.117(3) 0.088(3) 0.093(2) 0.003(2) 0.063(2) -0.015(2) C8 0.176(5) 0.088(3) 0.072(2) 0.021(2) 0.059(3) 0.003(3) C9 0.0790(19) 0.110(3) 0.0473(14) -0.0139(16) 0.0129(13) -0.0144(19) C10 0.116(3) 0.072(2) 0.081(2) -0.0098(17) 0.046(2) 0.0024(19) C11 0.0404(11) 0.0557(14) 0.0415(11) 0.0041(10) 0.0164(9) 0.0020(10) C12 0.0359(10) 0.0587(14) 0.0433(11) 0.0091(10) 0.0168(8) 0.0036(10) C13 0.0431(12) 0.0485(13) 0.0527(13) 0.0140(10) 0.0150(10) 0.0013(10) C14 0.0490(14) 0.086(2) 0.097(2) 0.0009(19) 0.0290(15) -0.0113(16) C15 0.0589(18) 0.085(2) 0.138(3) -0.011(2) 0.018(2) -0.0234(18) C16 0.081(2) 0.0568(17) 0.098(3) -0.0073(18) -0.009(2) -0.0071(16) C17 0.092(2) 0.0613(18) 0.0683(18) -0.0077(14) 0.0172(16) 0.0011(16) C18 0.0666(16) 0.0584(15) 0.0568(14) 0.0008(12) 0.0233(12) -0.0087(13) C19 0.0428(13) 0.0656(17) 0.0738(17) 0.0099(13) 0.0170(12) 0.0094(11) C20 0.084(2) 0.0533(16) 0.091(2) -0.0094(16) 0.0198(17) -0.0002(16) C21 0.0701(18) 0.107(2) 0.0490(14) -0.0105(16) 0.0262(12) -0.0045(18) _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 C22 1.745(9) . ? S1 C16 1.771(4) . ? N1 C20 1.485(4) . ? N1 C21 1.490(3) . ? N1 C11 1.508(3) . ? O1 C6 1.260(3) . ? O2 C6 1.245(3) . ? O3 C12 1.416(3) . ? O4 C19 1.401(4) . ? C1 C6 1.494(3) . ? C1 C2 1.516(4) . ? C1 C3 1.522(3) . ? C2 C10 1.506(5) . ? C2 C3 1.508(4) . ? C2 C9 1.509(5) . ? C3 C4 1.458(4) . ? C4 C5 1.332(4) . ? C5 C7 1.489(6) . ? C5 C8 1.496(5) . ? C11 C19 1.518(3) . ? C11 C12 1.541(3) . ? C12 C13 1.502(4) . ? C13 C18 1.374(4) . ? C13 C14 1.391(4) . ? C14 C15 1.347(6) . ? C15 C16 1.381(6) . ? C16 C17 1.399(6) . ? C17 C18 1.377(4) . ? 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 C22 S1 C16 105.5(4) . . ? C20 N1 C21 111.0(3) . . ? C20 N1 C11 112.3(2) . . ? C21 N1 C11 116.3(2) . . ? C6 C1 C2 119.9(2) . . ? C6 C1 C3 122.1(2) . . ? C2 C1 C3 59.52(18) . . ? C10 C2 C3 118.2(3) . . ? C10 C2 C9 113.2(3) . . ? C3 C2 C9 119.1(3) . . ? C10 C2 C1 119.3(3) . . ? C3 C2 C1 60.45(18) . . ? C9 C2 C1 117.0(3) . . ? C4 C3 C2 121.7(3) . . ? C4 C3 C1 119.8(2) . . ? C2 C3 C1 60.03(17) . . ? C5 C4 C3 127.9(3) . . ? C4 C5 C7 123.2(3) . . ? C4 C5 C8 121.0(4) . . ? C7 C5 C8 115.8(3) . . ? O2 C6 O1 123.2(2) . . ? O2 C6 C1 121.0(2) . . ? O1 C6 C1 115.7(2) . . ? N1 C11 C19 114.0(2) . . ? N1 C11 C12 109.95(18) . . ? C19 C11 C12 113.1(2) . . ? O3 C12 C13 110.8(2) . . ? O3 C12 C11 106.33(19) . . ? C13 C12 C11 111.09(18) . . ? C18 C13 C14 117.3(3) . . ? C18 C13 C12 121.3(2) . . ? C14 C13 C12 121.4(2) . . ? C15 C14 C13 122.1(3) . . ? C14 C15 C16 120.3(3) . . ? C15 C16 C17 119.3(3) . . ? C15 C16 S1 118.2(3) . . ? C17 C16 S1 122.4(4) . . ? C18 C17 C16 118.8(3) . . ? C13 C18 C17 122.2(3) . . ? O4 C19 C11 110.9(2) . . ? 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 C6 C1 C2 C10 4.2(4) . . . . ? C3 C1 C2 C10 -107.7(3) . . . . ? C6 C1 C2 C3 111.9(2) . . . . ? C6 C1 C2 C9 -138.4(3) . . . . ? C3 C1 C2 C9 109.8(3) . . . . ? C10 C2 C3 C4 -141.8(3) . . . . ? C9 C2 C3 C4 2.2(4) . . . . ? C1 C2 C3 C4 108.6(3) . . . . ? C10 C2 C3 C1 109.6(3) . . . . ? C9 C2 C3 C1 -106.4(3) . . . . ? C6 C1 C3 C4 140.1(3) . . . . ? C2 C1 C3 C4 -111.6(3) . . . . ? C6 C1 C3 C2 -108.3(3) . . . . ? C2 C3 C4 C5 135.1(4) . . . . ? C1 C3 C4 C5 -153.7(3) . . . . ? C3 C4 C5 C7 1.8(6) . . . . ? C3 C4 C5 C8 -177.1(3) . . . . ? C2 C1 C6 O2 -67.3(4) . . . . ? C3 C1 C6 O2 3.4(4) . . . . ? C2 C1 C6 O1 110.3(3) . . . . ? C3 C1 C6 O1 -179.0(3) . . . . ? C20 N1 C11 C19 -58.6(3) . . . . ? C21 N1 C11 C19 70.8(3) . . . . ? C20 N1 C11 C12 173.2(2) . . . . ? C21 N1 C11 C12 -57.4(3) . . . . ? N1 C11 C12 O3 -46.8(2) . . . . ? C19 C11 C12 O3 -175.43(19) . . . . ? N1 C11 C12 C13 -167.46(17) . . . . ? C19 C11 C12 C13 63.9(3) . . . . ? O3 C12 C13 C18 -35.3(3) . . . . ? C11 C12 C13 C18 82.6(3) . . . . ? O3 C12 C13 C14 141.6(3) . . . . ? C11 C12 C13 C14 -100.4(3) . . . . ? C18 C13 C14 C15 -0.9(5) . . . . ? C12 C13 C14 C15 -178.0(3) . . . . ? C13 C14 C15 C16 0.0(6) . . . . ? C14 C15 C16 C17 0.4(6) . . . . ? C14 C15 C16 S1 177.4(4) . . . . ? C22 S1 C16 C15 166.5(4) . . . . ? C22 S1 C16 C17 -16.7(5) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? S1 C16 C17 C18 -176.8(3) . . . . ? C14 C13 C18 C17 1.4(4) . . . . ? C12 C13 C18 C17 178.5(3) . . . . ? C16 C17 C18 C13 -0.9(5) . . . . ? N1 C11 C19 O4 -69.5(3) . . . . ? C12 C11 C19 O4 57.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.85(4) 1.88(4) 2.682(3) 156(3) 2_746 O3 H31 O1 0.82 1.80 2.621(2) 174.5 1_545 O4 H41 O2 0.82 1.88 2.677(3) 164.2 2_646 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.323 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.039