# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/194 data_AI1-re _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(R)-2-Phenylpropionic Acid ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(R)-3a. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chenmistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japan ; _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _chemical_formula_moiety 'C18 H21 N1 O3 ' _chemical_formula_weight 299.00 _cell_length_a 12.121(4) _cell_length_b 6.319(2) _cell_length_c 10.882(4) _cell_angle_alpha 90.000000(0) _cell_angle_beta 102.69(3) _cell_angle_gamma 90.000000(0) _cell_volume 813.1(5) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_meas 1.221 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.668 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1627 _reflns_number_total 1454 _reflns_number_observed 1403 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_theta_max 51.41 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.061 _refine_ls_wR_factor_obs 0.075 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1403 _refine_ls_number_parameters 201 _refine_ls_goodness_of_fit_obs 1.160 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0250 _refine_ls_shift/esd_mean 0.0063 _refine_diff_density_min -0.27 _refine_diff_density_max 0.24 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.04684 _diffrn_orient_matrix_UB_12 0.04290 _diffrn_orient_matrix_UB_13 -0.06086 _diffrn_orient_matrix_UB_21 -0.07038 _diffrn_orient_matrix_UB_22 0.02449 _diffrn_orient_matrix_UB_23 -0.06612 _diffrn_orient_matrix_UB_31 -0.00190 _diffrn_orient_matrix_UB_32 0.15038 _diffrn_orient_matrix_UB_33 0.02831 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,+Y+0.5,-Z _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O1 -0.71780(9) 0.01690 -0.61464(11) 0.0547(7) 1.000 Uij O15 -0.43616(10) -0.24179(33) -0.53230(10) 0.0510(7) 1.000 Uij O3 -0.79557(12) 0.30605(34) -0.71253(14) 0.0657(8) 1.000 Uij N12 -0.64514(10) -0.39214(35) -0.62734(11) 0.0443(7) 1.000 Uij C2 -0.79086(13) 0.11078(41) -0.69788(16) 0.0494(9) 1.000 Uij C4 -0.88123(14) -0.02153(40) -0.78336(17) 0.0527(9) 1.000 Uij C5 -0.92480(18) 0.08286(54) -0.91053(17) 0.073(1) 1.000 Uij C6 -0.97798(13) -0.06445(42) -0.71781(17) 0.0524(9) 1.000 Uij C7 -1.02356(17) 0.09614(48) -0.65945(20) 0.070(1) 1.000 Uij C8 -1.11246(19) 0.05459(64) -0.60059(22) 0.086(2) 1.000 Uij C9 -1.1580(2) -0.1392(7) -0.6034(2) 0.094(2) 1.000 Uij C10 -1.1154(3) -0.3009(7) -0.6632(3) 0.104(2) 1.000 Uij C11 -1.0250(2) -0.2623(5) -0.7208(2) 0.079(1) 1.000 Uij C13 -0.56278(12) -0.41903(37) -0.71116(14) 0.0460(8) 1.000 Uij C14 -0.45712(13) -0.28053(41) -0.66378(14) 0.0463(8) 1.000 Uij C16 -0.47937(15) -0.07621(43) -0.73829(17) 0.057(1) 1.000 Uij C17 -0.56249(15) -0.14098(44) -0.85657(17) 0.056(1) 1.000 Uij C18 -0.59409(19) -0.03440(54) -0.97062(20) 0.079(1) 1.000 Uij C19 -0.6747(2) -0.1271(7) -1.0652(2) 0.091(2) 1.000 Uij C20 -0.72233(18) -0.31869(69) -1.04968(19) 0.089(2) 1.000 Uij C21 -0.69102(16) -0.42591(52) -0.93668(16) 0.069(1) 1.000 Uij C22 -0.61008(13) -0.33520(41) -0.84070(15) 0.0505(9) 1.000 Uij H15 -0.3854(17) -0.3247(36) -0.4977(17) 0.049 1.000 Uiso H4 -0.84693 -0.15323 -0.79836 0.052 1.000 Uiso H5A -0.98000 -0.00364 -0.96473 0.071 1.000 Uiso H5B -0.86350 0.11096 -0.95113 0.071 1.000 Uiso H5C -0.95910 0.21456 -0.89553 0.071 1.000 Uiso H11 -0.99611 -0.37431 -0.76437 0.076 1.000 Uiso H10 -1.14713 -0.43997 -0.66259 0.101 1.000 Uiso H9 -1.22125 -0.16172 -0.56500 0.092 1.000 Uiso H8 -1.14206 0.16839 -0.55909 0.085 1.000 Uiso H7 -0.99156 0.23544 -0.65785 0.069 1.000 Uiso H12A -0.71014 -0.48054 -0.65564 0.043 1.000 Uiso H12B -0.66844 -0.24674 -0.63004 0.043 1.000 Uiso H12C -0.60964 -0.42864 -0.54214 0.043 1.000 Uiso H13 -0.53948 -0.56453 -0.70846 0.045 1.000 Uiso H14 -0.39242 -0.34713 -0.68458 0.045 1.000 Uiso H16A -0.41137 -0.01931 -0.75679 0.056 1.000 Uiso H16B -0.51227 0.02759 -0.69269 0.056 1.000 Uiso H18 -0.56069 0.09960 -0.98262 0.078 1.000 Uiso H19 -0.69805 -0.05675 -1.14492 0.090 1.000 Uiso H20 -0.77823 -0.37819 -1.11718 0.087 1.000 Uiso H21 -0.72282 -0.56101 -0.92378 0.067 1.000 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 0.0425(6) 0.0545(8) 0.0611(7) 0.0048(6) -.0041(5) -.0086(6) O15 0.0424(6) 0.0580(8) 0.0469(6) 0.0041(6) -.0050(5) -.0057(6) O3 0.0587(8) 0.0523(9) 0.0777(9) -.0136(7) -.0059(7) 0.0069(7) N12 0.0406(6) 0.0456(8) 0.0431(6) -.0044(6) 0.0032(5) 0.0020(7) C2 0.0375(8) 0.0520(12) 0.0563(9) -.0034(8) 0.0106(7) -.0013(9) C4 0.0434(8) 0.0508(12) 0.0603(9) -.0039(8) 0.0076(7) -.0041(9) C5 0.070(1) 0.092(2) 0.052(1) -0.020(1) 0.001(1) -0.003(1) C6 0.0372(8) 0.0613(12) 0.0530(9) -.0149(9) -.0047(7) 0.0066(9) C7 0.053(1) 0.080(2) 0.074(1) -0.014(1) 0.015(1) -0.005(1) C8 0.054(1) 0.126(3) 0.074(1) -0.012(2) 0.015(1) -0.003(2) C9 0.057(1) 0.147(3) 0.073(1) -0.031(2) 0.007(1) 0.018(2) C10 0.081(2) 0.111(3) 0.110(2) -0.058(2) 0.003(2) 0.029(2) C11 0.068(1) 0.076(2) 0.086(1) -0.031(1) 0.003(1) 0.011(1) C13 0.0436(8) 0.0445(10) 0.0466(8) 0.0045(8) 0.0060(6) -.0036(8) C14 0.0406(8) 0.0499(11) 0.0453(8) 0.0001(8) 0.0049(6) -.0032(8) C16 0.0540(9) 0.0548(12) 0.0591(10) -.0088(9) 0.0110(8) 0.0036(9) C17 0.0471(9) 0.0727(14) 0.0479(8) 0.0044(10) 0.0146(7) 0.0105(10) C18 0.073(1) 0.096(2) 0.064(1) 0.013(1) 0.023(1) 0.029(1) C19 0.073(1) 0.146(3) 0.050(1) 0.018(2) 0.012(1) 0.027(2) C20 0.059(1) 0.152(3) 0.049(1) -0.001(2) 0.000(1) 0.001(2) C21 0.0543(9) 0.0985(19) 0.0485(9) -.0066(12) 0.0041(7) -.0091(11) C22 0.0406(8) 0.0664(13) 0.0422(8) 0.0025(8) 0.0075(6) -.0023(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.267(3) . . yes O15 C14 1.418(2) . . yes O3 C2 1.244(4) . . yes N12 C13 1.503(2) . . yes C2 C4 1.522(3) . . yes C4 C5 1.519(3) . . yes C4 C6 1.525(3) . . yes C6 C7 1.376(4) . . yes C6 C11 1.372(5) . . yes C7 C8 1.394(4) . . yes C8 C9 1.341(6) . . yes C9 C10 1.372(6) . . yes C10 C11 1.398(4) . . yes C13 C14 1.543(3) . . yes C13 C22 1.497(3) . . yes C14 C16 1.517(4) . . yes C16 C17 1.506(3) . . yes C17 C18 1.390(4) . . yes C17 C22 1.383(4) . . yes C18 C19 1.384(4) . . yes C19 C20 1.367(6) . . yes C20 C21 1.382(4) . . yes C21 C22 1.390(3) . . yes O15 H15 0.83(3) . . yes N12 H12A 0.960(2) . . yes N12 H12B 0.960(3) . . yes N12 H12C 0.961(2) . . yes C4 H4 0.960(3) . . yes C5 H5A 0.960(3) . . yes C5 H5B 0.961(3) . . yes C5 H5C 0.960(4) . . yes C7 H7 0.961(3) . . yes C8 H8 0.960(4) . . yes C9 H9 0.960(3) . . yes C10 H10 0.960(4) . . yes C11 H11 0.960(3) . . yes C13 H13 0.960(3) . . yes C14 H14 0.960(2) . . yes C16 H16A 0.960(2) . . yes C16 H16B 0.960(3) . . yes C18 H18 0.960(4) . . yes C19 H19 0.960(3) . . yes C20 H20 0.960(3) . . yes C21 H21 0.960(4) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 124.2(2) . . . yes O1 C2 C4 118.4(3) . . . yes O3 C2 C4 117.4(2) . . . yes C2 C4 C5 112.2(3) . . . yes C2 C4 C6 109.6(2) . . . yes C5 C4 C6 110.7(2) . . . yes C4 C6 C7 120.9(3) . . . yes C4 C6 C11 120.6(3) . . . yes C7 C6 C11 118.4(2) . . . yes C6 C7 C8 120.2(3) . . . yes C7 C8 C9 121.2(3) . . . yes C8 C9 C10 119.6(3) . . . yes C9 C10 C11 119.8(4) . . . yes C6 C11 C10 120.7(3) . . . yes N12 C13 C14 110.3(2) . . . yes N12 C13 C22 111.3(2) . . . yes C14 C13 C22 103.4(2) . . . yes O15 C14 C13 112.7(2) . . . yes O15 C14 C16 111.3(2) . . . yes C13 C14 C16 105.5(2) . . . yes C14 C16 C17 103.4(2) . . . yes C16 C17 C18 129.2(3) . . . yes C16 C17 C22 110.7(2) . . . yes C18 C17 C22 120.1(2) . . . yes C17 C18 C19 118.0(3) . . . yes C18 C19 C20 122.1(3) . . . yes C19 C20 C21 120.2(3) . . . yes C20 C21 C22 118.5(3) . . . yes C13 C22 C17 110.3(2) . . . yes C13 C22 C21 128.5(3) . . . yes C17 C22 C21 121.1(2) . . . yes C14 O15 H15 107.3(14) . . . yes C13 N12 H12A 110.3(2) . . . yes C13 N12 H12B 108.7(2) . . . yes C13 N12 H12C 110.0(2) . . . yes H12A N12 H12B 109.4(2) . . . yes H12A N12 H12C 109.4(2) . . . yes H12B N12 H12C 109.0(2) . . . yes C2 C4 H4 107.4(2) . . . yes C5 C4 H4 107.4(2) . . . yes C6 C4 H4 109.4(3) . . . yes C4 C5 H5A 111.6(3) . . . yes C4 C5 H5B 110.5(2) . . . yes C4 C5 H5C 107.4(2) . . . yes H5A C5 H5B 109.1(3) . . . yes H5A C5 H5C 109.2(3) . . . yes H5B C5 H5C 109.0(4) . . . yes C6 C7 H7 118.9(2) . . . yes C8 C7 H7 120.9(3) . . . yes C7 C8 H8 118.8(4) . . . yes C9 C8 H8 120.0(3) . . . yes C8 C9 H9 119.3(4) . . . yes C10 C9 H9 121.0(5) . . . yes C9 C10 H10 119.1(4) . . . yes C11 C10 H10 121.1(4) . . . yes C6 C11 H11 119.3(3) . . . yes C10 C11 H11 120.0(4) . . . yes N12 C13 H13 108.7(2) . . . yes C14 C13 H13 108.4(2) . . . yes C22 C13 H13 114.6(2) . . . yes O15 C14 H14 109.8(2) . . . yes C13 C14 H14 109.5(3) . . . yes C16 C14 H14 107.8(2) . . . yes C14 C16 H16A 111.8(2) . . . yes C14 C16 H16B 110.5(2) . . . yes C17 C16 H16A 111.5(2) . . . yes C17 C16 H16B 110.6(2) . . . yes H16A C16 H16B 109.0(3) . . . yes C17 C18 H18 120.5(3) . . . yes C19 C18 H18 121.5(3) . . . yes C18 C19 H19 119.7(4) . . . yes C20 C19 H19 118.3(3) . . . yes C19 C20 H20 119.9(3) . . . yes C21 C20 H20 119.9(4) . . . yes C20 C21 H21 121.7(3) . . . yes C22 C21 H21 119.8(3) . . . yes #===END data_AI1m _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(R)-2-(m-Tolyl)propionic Acid ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(R)-3c. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chemistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japan ; _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _chemical_formula_moiety 'C19 H23 N1 O3 ' _chemical_formula_weight 313.00 _cell_length_a 12.294(5) _cell_length_b 6.388(4) _cell_length_c 11.134(5) _cell_angle_alpha 90.000000(0) _cell_angle_beta 103.71(3) _cell_angle_gamma 90.000000(0) _cell_volume 849.5(7) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_meas 1.223 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.661 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1680 _reflns_number_total 1288 _reflns_number_observed 1260 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_theta_max 51.32 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.086 _refine_ls_wR_factor_obs 0.086 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1260 _refine_ls_number_parameters 207 _refine_ls_goodness_of_fit_obs 1.051 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.4467 _refine_ls_shift/esd_mean 0.0202 _refine_diff_density_min -0.31 _refine_diff_density_max 0.31 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.07149 _diffrn_orient_matrix_UB_12 -0.05444 _diffrn_orient_matrix_UB_13 0.05334 _diffrn_orient_matrix_UB_21 0.03664 _diffrn_orient_matrix_UB_22 0.01273 _diffrn_orient_matrix_UB_23 -0.07083 _diffrn_orient_matrix_UB_31 0.02362 _diffrn_orient_matrix_UB_32 0.14625 _diffrn_orient_matrix_UB_33 0.02618 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,+Y+0.5,-Z _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O1 1.2931(5) 0.0290 0.3807(6) 0.052(4) 1.000 Uij O3 1.2118(6) 0.3142(15) 0.2891(6) 0.058(4) 1.000 Uij O16 1.5667(5) -0.2250(14) 0.4657(5) 0.051(4) 1.000 Uij N13 1.3611(6) -0.3799(15) 0.3697(6) 0.044(4) 1.000 Uij C2 1.2202(7) 0.1217(20) 0.2993(8) 0.047(6) 1.000 Uij C4 1.1379(7) -0.0116(18) 0.2063(8) 0.047(5) 1.000 Uij C5 1.0908(9) 0.1003(23) 0.0839(8) 0.070(7) 1.000 Uij C6 1.0420(7) -0.0860(19) 0.2602(8) 0.043(5) 1.000 Uij C7 1.0070(9) -0.2946(22) 0.2444(11) 0.072(8) 1.000 Uij C8 0.9163(10) -0.3586(25) 0.2884(13) 0.085(9) 1.000 Uij C9 0.8658(9) -0.2264(25) 0.3550(11) 0.077(8) 1.000 Uij C10 0.8984(8) -0.0194(22) 0.3719(9) 0.060(6) 1.000 Uij C11 0.8397(9) 0.1243(29) 0.4427(10) 0.086(9) 1.000 Uij C12 0.9889(8) 0.0421(20) 0.3258(8) 0.053(6) 1.000 Uij C14 1.4427(7) -0.4070(18) 0.2920(8) 0.047(5) 1.000 Uij C15 1.5469(7) -0.2731(20) 0.3382(8) 0.051(6) 1.000 Uij C18 1.4428(8) -0.1417(20) 0.1435(8) 0.054(6) 1.000 Uij C19 1.3954(7) -0.3338(19) 0.1623(7) 0.046(5) 1.000 Uij C20 1.3163(8) -0.4275(22) 0.0687(9) 0.067(7) 1.000 Uij C21 1.2832(10) -0.3272(31) -0.0442(10) 0.09(1) 1.000 Uij C22 1.3308(11) -0.1390(28) -0.0629(10) 0.080(9) 1.000 Uij C23 1.4100(10) -0.0476(22) 0.0302(10) 0.070(7) 1.000 Uij C24 1.5248(9) -0.0736(21) 0.2594(9) 0.063(7) 1.000 Uij H4 1.17710 -0.13130 0.18569 0.046 1.000 Uiso H5A 1.15168 0.14659 0.05028 0.068 1.000 Uiso H5B 1.04768 0.21869 0.09868 0.068 1.000 Uiso H5C 1.04328 0.00789 0.02638 0.068 1.000 Uiso H7 1.04314 -0.39133 0.20044 0.069 1.000 Uiso H8 0.88902 -0.49945 0.27483 0.082 1.000 Uiso H9 0.80665 -0.27670 0.39019 0.076 1.000 Uiso H11A 0.77712 0.07884 0.47357 0.086 1.000 Uiso H11B 0.81342 0.23914 0.38787 0.086 1.000 Uiso H11C 0.89472 0.17504 0.51277 0.086 1.000 Uiso H12 1.01597 0.18275 0.34148 0.051 1.000 Uiso H13A 1.39244 -0.42957 0.45199 0.043 1.000 Uiso H13B 1.29364 -0.45547 0.33449 0.043 1.000 Uiso H13C 1.34384 -0.23357 0.37229 0.043 1.000 Uiso H14 1.45999 -0.55317 0.28938 0.046 1.000 Uiso H15 1.61127 -0.34050 0.32086 0.049 1.000 Uiso H16 1.627(4) -0.294(8) 0.511(4) 0.048 1.000 Uiso H20 1.28315 -0.55811 0.08341 0.066 1.000 Uiso H21 1.22834 -0.38979 -0.11029 0.086 1.000 Uiso H22 1.30688 -0.07097 -0.14173 0.079 1.000 Uiso H23 1.44239 0.08295 0.01401 0.069 1.000 Uiso H24A 1.59273 -0.02296 0.24132 0.062 1.000 Uiso H24B 1.494(4) 0.034(8) 0.301(4) 0.062 1.000 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 0.060(4) 0.036(4) 0.052(4) 0.005(4) -0.001(3) -0.006(3) O3 0.065(4) 0.037(4) 0.065(4) -0.007(4) 0.001(4) -0.001(4) O16 0.060(4) 0.044(4) 0.040(3) 0.005(3) -0.007(3) -0.005(3) N13 0.061(5) 0.031(4) 0.036(4) -0.005(4) 0.004(3) -0.002(4) C2 0.042(5) 0.049(6) 0.047(5) -0.005(5) 0.010(4) -0.011(5) C4 0.055(5) 0.036(6) 0.046(5) -0.002(5) 0.011(4) -0.012(5) C5 0.091(8) 0.071(8) 0.040(5) -0.024(7) 0.002(5) 0.000(6) C6 0.045(5) 0.041(5) 0.037(5) -0.008(4) -0.005(4) 0.001(4) C7 0.069(7) 0.064(8) 0.076(7) 0.002(7) 0.000(6) -0.013(7) C8 0.072(8) 0.067(9) 0.108(10) -0.032(7) 0.010(7) 0.012(8) C9 0.056(7) 0.090(11) 0.083(8) -0.032(7) 0.019(6) 0.017(8) C10 0.042(5) 0.081(9) 0.052(6) -0.006(6) -0.002(4) 0.004(6) C11 0.065(7) 0.122(12) 0.070(7) 0.002(9) 0.023(5) -0.003(9) C12 0.050(5) 0.053(6) 0.050(5) -0.021(5) 0.005(4) -0.001(5) C14 0.052(5) 0.041(6) 0.045(5) 0.002(5) 0.016(4) -0.006(4) C15 0.047(5) 0.048(6) 0.053(5) 0.002(5) 0.007(4) -0.002(5) C18 0.053(6) 0.064(7) 0.044(5) -0.002(5) 0.015(4) 0.000(5) C19 0.039(4) 0.063(7) 0.034(5) 0.002(5) 0.008(4) 0.000(5) C20 0.066(6) 0.079(9) 0.051(6) -0.007(7) 0.016(5) 0.003(6) C21 0.070(7) 0.150(16) 0.039(6) 0.001(10) -0.003(5) -0.013(9) C22 0.087(9) 0.103(12) 0.046(6) 0.018(9) 0.016(6) 0.012(7) C23 0.082(7) 0.070(8) 0.056(6) 0.006(7) 0.019(6) 0.017(6) C24 0.076(7) 0.052(7) 0.058(6) -0.013(6) 0.019(5) 0.003(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.261(12) . . yes O3 C2 1.237(16) . . yes O16 C15 1.417(11) . . yes N13 C14 1.482(11) . . yes C2 C4 1.525(14) . . yes C4 C5 1.526(14) . . yes C4 C6 1.521(13) . . yes C6 C7 1.399(19) . . yes C6 C12 1.361(15) . . yes C7 C8 1.382(18) . . yes C8 C9 1.37(2) . . yes C9 C10 1.38(3) . . yes C10 C11 1.501(19) . . yes C10 C12 1.387(14) . . yes C14 C15 1.524(14) . . yes C14 C19 1.497(12) . . yes C15 C24 1.534(17) . . yes C18 C19 1.396(17) . . yes C18 C23 1.369(16) . . yes C18 C24 1.501(15) . . yes C19 C20 1.382(14) . . yes C20 C21 1.383(18) . . yes C21 C22 1.37(3) . . yes C22 C23 1.373(18) . . yes O16 H16 0.91(5) . . yes N13 H13A 0.960(7) . . yes N13 H13B 0.960(8) . . yes N13 H13C 0.960(10) . . yes C4 H4 0.960(11) . . yes C5 H5A 0.960(11) . . yes C5 H5B 0.960(14) . . yes C5 H5C 0.960(12) . . yes C7 H7 0.960(13) . . yes C8 H8 0.960(16) . . yes C9 H9 0.960(12) . . yes C11 H11A 0.960(12) . . yes C11 H11B 0.960(16) . . yes C11 H11C 0.960(12) . . yes C12 H12 0.960(13) . . yes C14 H14 0.960(12) . . yes C15 H15 0.960(10) . . yes C20 H20 0.960(14) . . yes C21 H21 0.960(13) . . yes C22 H22 0.961(13) . . yes C23 H23 0.960(14) . . yes C24 H24A 0.960(11) . . yes C24 H24B 0.96(6) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 124.2(9) . . . yes O1 C2 C4 118.1(10) . . . yes O3 C2 C4 117.7(9) . . . yes C2 C4 C5 113.3(10) . . . yes C2 C4 C6 111.0(8) . . . yes C5 C4 C6 109.5(8) . . . yes C4 C6 C7 119.5(10) . . . yes C4 C6 C12 122.6(11) . . . yes C7 C6 C12 117.9(10) . . . yes C6 C7 C8 119.1(12) . . . yes C7 C8 C9 121.2(14) . . . yes C8 C9 C10 120.8(12) . . . yes C9 C10 C11 119.8(11) . . . yes C9 C10 C12 116.9(11) . . . yes C11 C10 C12 123.2(13) . . . yes C6 C12 C10 123.8(12) . . . yes N13 C14 C15 111.6(8) . . . yes N13 C14 C19 111.4(8) . . . yes C15 C14 C19 104.7(9) . . . yes O16 C15 C14 113.0(8) . . . yes O16 C15 C24 111.0(10) . . . yes C14 C15 C24 104.6(8) . . . yes C19 C18 C23 118.8(10) . . . yes C19 C18 C24 110.2(9) . . . yes C23 C18 C24 131.0(12) . . . yes C14 C19 C18 109.8(9) . . . yes C14 C19 C20 129.4(11) . . . yes C18 C19 C20 120.8(10) . . . yes C19 C20 C21 119.2(13) . . . yes C20 C21 C22 119.9(12) . . . yes C21 C22 C23 120.5(12) . . . yes C18 C23 C22 120.7(13) . . . yes C15 C24 C18 104.0(10) . . . yes C15 O16 H16 111.8(29) . . . yes C14 N13 H13A 110.2(7) . . . yes C14 N13 H13B 110.0(8) . . . yes C14 N13 H13C 108.5(8) . . . yes H13A N13 H13B 109.6(9) . . . yes H13A N13 H13C 109.5(8) . . . yes H13B N13 H13C 109.0(8) . . . yes C2 C4 H4 108.5(8) . . . yes C5 C4 H4 105.4(9) . . . yes C6 C4 H4 109.0(10) . . . yes C4 C5 H5A 109.1(10) . . . yes C4 C5 H5B 108.9(9) . . . yes C4 C5 H5C 110.5(12) . . . yes H5A C5 H5B 109.7(14) . . . yes H5A C5 H5C 109.7(10) . . . yes H5B C5 H5C 109.0(11) . . . yes C6 C7 H7 120.8(11) . . . yes C8 C7 H7 120.0(14) . . . yes C7 C8 H8 120.2(14) . . . yes C9 C8 H8 118.6(13) . . . yes C8 C9 H9 120.0(16) . . . yes C10 C9 H9 119.2(13) . . . yes C10 C11 H11A 121.9(17) . . . yes C10 C11 H11B 105.4(10) . . . yes C10 C11 H11C 107.4(10) . . . yes H11A C11 H11B 106.3(12) . . . yes H11A C11 H11C 106.3(11) . . . yes H11B C11 H11C 109.0(18) . . . yes C6 C12 H12 118.0(10) . . . yes C10 C12 H12 118.1(11) . . . yes N13 C14 H14 108.5(9) . . . yes C15 C14 H14 112.4(9) . . . yes C19 C14 H14 108.2(9) . . . yes O16 C15 H15 110.1(8) . . . yes C14 C15 H15 110.3(11) . . . yes C24 C15 H15 107.5(9) . . . yes C19 C20 H20 120.0(11) . . . yes C21 C20 H20 120.8(12) . . . yes C20 C21 H21 120.4(17) . . . yes C22 C21 H21 119.7(14) . . . yes C21 C22 H22 119.0(13) . . . yes C23 C22 H22 120.4(16) . . . yes C18 C23 H23 120.6(12) . . . yes C22 C23 H23 118.6(12) . . . yes C15 C24 H24A 110.8(10) . . . yes C15 C24 H24B 111.0(31) . . . yes C18 C24 H24A 110.9(9) . . . yes C18 C24 H24B 111.1(30) . . . yes H24A C24 H24B 109.0(32) . . . yes #===END data_AI3 _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(R)-2-(p-Methoxyphenyl)propionic Acid/H2O ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(R)-3e/H2O. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chemistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japan ; _chemical_compound_source 'Saigol laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _chemical_formula_moiety 'C19 H25 N1 O5 ' _chemical_formula_weight 347.41 _cell_length_a 14.584(4) _cell_length_b 6.175(3) _cell_length_c 10.852(3) _cell_angle_alpha 90.000000(0) _cell_angle_beta 107.80(2) _cell_angle_gamma 90.000000(0) _cell_volume 930.6(6) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_meas 1.240 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.735 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1846 _reflns_number_total 1647 _reflns_number_observed 1563 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_theta_max 51.32 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.045 _refine_ls_wR_factor_obs 0.057 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1563 _refine_ls_number_parameters 235 _refine_ls_goodness_of_fit_obs 1.146 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0739 _refine_ls_shift/esd_mean 0.0084 _refine_diff_density_min -0.24 _refine_diff_density_max 0.16 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.01172 _diffrn_orient_matrix_UB_12 -0.03316 _diffrn_orient_matrix_UB_13 0.09375 _diffrn_orient_matrix_UB_21 0.07035 _diffrn_orient_matrix_UB_22 -0.01668 _diffrn_orient_matrix_UB_23 0.01169 _diffrn_orient_matrix_UB_31 0.00997 _diffrn_orient_matrix_UB_32 0.15763 _diffrn_orient_matrix_UB_33 0.02100 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,+Y+0.5,-Z _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O1 1.30466(7) 0.33000 0.36152(9) 0.0505(6) 1.000 Uij O3 1.23682(8) 0.62182(27) 0.25282(11) 0.0631(7) 1.000 Uij O12 0.85101(8) 0.24917(35) 0.38273(14) 0.0888(9) 1.000 Uij O17 1.55497(7) 0.06307(25) 0.47350(8) 0.0477(5) 1.000 Uij O24 1.28570(10) 0.07162(37) 0.57305(13) 0.104(1) 1.000 Uij N14 1.37655(7) -0.08890(27) 0.35592(9) 0.0394(6) 1.000 Uij C2 1.24192(9) 0.42218(31) 0.26893(13) 0.0448(8) 1.000 Uij C4 1.16628(10) 0.28141(36) 0.17688(15) 0.0558(9) 1.000 Uij C5 1.13920(12) 0.36393(47) 0.03782(15) 0.084(1) 1.000 Uij C6 1.08082(10) 0.26431(32) 0.23006(14) 0.0486(8) 1.000 Uij C7 1.02054(11) 0.44047(34) 0.22463(17) 0.063(1) 1.000 Uij C8 0.94506(11) 0.43097(38) 0.27655(19) 0.069(1) 1.000 Uij C9 0.92888(10) 0.24260(38) 0.33434(15) 0.060(1) 1.000 Uij C10 0.98791(12) 0.06777(38) 0.34162(18) 0.067(1) 1.000 Uij C11 1.06331(11) 0.08028(34) 0.28925(18) 0.0619(9) 1.000 Uij C13 0.82321(15) 0.05550(55) 0.43106(24) 0.107(2) 1.000 Uij C15 1.44717(9) -0.12096(27) 0.28334(12) 0.0395(7) 1.000 Uij C16 1.53635(9) 0.02297(29) 0.33967(12) 0.0427(7) 1.000 Uij C18 1.51416(11) 0.23226(33) 0.26256(14) 0.0524(9) 1.000 Uij C19 1.44588(9) 0.16122(31) 0.13481(13) 0.0457(8) 1.000 Uij C20 1.41993(11) 0.26386(38) 0.01417(14) 0.062(1) 1.000 Uij C21 1.35595(12) 0.16433(44) -0.08907(16) 0.071(1) 1.000 Uij C22 1.31748(11) -0.03636(45) -0.07734(15) 0.069(1) 1.000 Uij C23 1.34213(10) -0.14102(35) 0.04059(13) 0.0556(9) 1.000 Uij C24 1.40757(9) -0.04008(31) 0.14683(12) 0.0423(7) 1.000 Uij H24A 1.253(4) 0.137(12) 0.491(6) 0.101 1.000 Uiso H17 1.5904(11) 0.0031(32) 0.5114(15) 0.045 1.000 Uiso H24B 1.2554(13) -0.0120(46) 0.6242(18) 0.101 1.000 Uiso H4 1.19218 0.13841 0.17708 0.053 1.000 Uiso H5A 1.09170 0.27363 -0.02028 0.082 1.000 Uiso H5B 1.19510 0.37163 0.00882 0.082 1.000 Uiso H5C 1.11330 0.50693 0.03762 0.082 1.000 Uiso H7 1.03204 0.57207 0.18463 0.060 1.000 Uiso H8 0.90316 0.55297 0.27065 0.067 1.000 Uiso H13A 0.76971 0.05790 0.46506 0.105 1.000 Uiso H13B 0.87781 0.00160 0.49826 0.105 1.000 Uiso H13C 0.80751 -0.04470 0.36006 0.105 1.000 Uiso H10 0.97661 -0.06163 0.38382 0.064 1.000 Uiso H11 1.10391 -0.04312 0.29195 0.059 1.000 Uiso H14A 1.32135 -0.18020 0.32152 0.038 1.000 Uiso H14B 1.35675 0.06000 0.34702 0.038 1.000 Uiso H14C 1.40565 -0.12090 0.44602 0.038 1.000 Uiso H15 1.46697 -0.26986 0.29224 0.038 1.000 Uiso H16 1.59155 -0.04563 0.32597 0.032(3) 1.000 Uiso H18A 1.57116 0.29796 0.25266 0.072(5) 1.000 Uiso H18B 1.48336 0.33306 0.30446 0.055(5) 1.000 Uiso H20 1.44723 0.40236 0.00547 0.052(4) 1.000 Uiso H21 1.33725 0.23443 -0.17197 0.070(5) 1.000 Uiso H22 1.27358 -0.10346 -0.15204 0.057(4) 1.000 Uiso H23 1.31453 -0.27822 0.05129 0.049(4) 1.000 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 0.0470(5) 0.0476(6) 0.0486(5) 0.0025(5) 0.0049(4) -.0060(5) O3 0.0518(6) 0.0484(8) 0.0763(8) -.0098(6) 0.0012(5) 0.0086(6) O12 0.0593(7) 0.0991(11) 0.1041(10) -.0153(8) 0.0383(7) 0.0036(9) O17 0.0498(6) 0.0501(7) 0.0349(5) 0.0059(5) 0.0011(4) -.0074(5) O24 0.108(1) 0.118(1) 0.076(1) 0.004(1) 0.027(1) 0.019(1) N14 0.0415(5) 0.0371(7) 0.0347(5) -.0024(5) 0.0088(4) 0.0047(5) C2 0.0337(7) 0.0470(10) 0.0494(8) -.0022(7) 0.0131(6) -.0034(8) C4 0.0449(8) 0.0607(11) 0.0547(8) -.0093(8) 0.0091(7) -.0149(8) C5 0.068(1) 0.123(2) 0.053(1) -0.021(1) 0.011(1) -0.012(1) C6 0.0362(7) 0.0466(9) 0.0547(8) -.0074(7) 0.0027(6) -.0019(7) C7 0.0452(8) 0.0510(10) 0.0831(11) -.0005(8) 0.0141(8) 0.0159(10) C8 0.0425(8) 0.0575(11) 0.0999(13) 0.0037(9) 0.0199(8) 0.0052(11) C9 0.0430(8) 0.0698(12) 0.0607(9) -.0127(9) 0.0125(7) 0.0039(9) C10 0.0571(9) 0.0576(11) 0.0762(11) -.0098(9) 0.0121(8) 0.0142(9) C11 0.0486(8) 0.0478(10) 0.0800(11) -.0021(8) 0.0116(8) 0.0046(9) C13 0.071(1) 0.129(2) 0.113(2) -0.024(2) 0.038(1) 0.027(2) C15 0.0422(7) 0.0324(8) 0.0395(7) 0.0035(6) 0.0121(5) -.0023(6) C16 0.0393(7) 0.0459(9) 0.0382(7) 0.0023(7) 0.0100(6) -.0080(6) C18 0.0579(9) 0.0471(9) 0.0477(8) -.0125(8) 0.0195(7) -.0027(7) C19 0.0473(7) 0.0486(9) 0.0388(7) 0.0030(7) 0.0193(6) 0.0048(7) C20 0.068(1) 0.068(1) 0.049(1) 0.010(1) 0.028(1) 0.016(1) C21 0.065(1) 0.101(2) 0.043(1) 0.015(1) 0.020(1) 0.020(1) C22 0.0521(9) 0.1081(18) 0.0397(8) 0.0039(11) 0.0043(7) -.0062(10) C23 0.0505(8) 0.0676(11) 0.0431(8) -.0078(8) 0.0124(7) -.0088(8) C24 0.0412(7) 0.0470(9) 0.0351(7) 0.0010(7) 0.0126(6) -.0023(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.268(2) . . yes O3 C2 1.244(3) . . yes O12 C9 1.390(2) . . yes O12 C13 1.414(4) . . yes O17 C16 1.415(2) . . yes N14 C15 1.489(2) . . yes C2 C4 1.516(3) . . yes C4 C5 1.526(3) . . yes C4 C6 1.529(3) . . yes C6 C7 1.389(3) . . yes C6 C11 1.367(3) . . yes C7 C8 1.383(3) . . yes C8 C9 1.376(4) . . yes C9 C10 1.368(3) . . yes C10 C11 1.386(3) . . yes C15 C16 1.539(3) . . yes C15 C24 1.502(2) . . yes C16 C18 1.520(3) . . yes C18 C19 1.504(3) . . yes C19 C20 1.399(3) . . yes C19 C24 1.385(3) . . yes C20 C21 1.365(3) . . yes C21 C22 1.382(4) . . yes C22 C23 1.380(3) . . yes C23 C24 1.399(3) . . yes O17 H17 0.666(17) . . yes O24 H24A 0.96(7) . . yes O24 H24B 0.96(3) . . yes N14 H14A 0.960(2) . . yes N14 H14B 0.960(2) . . yes N14 H14C 0.960(1) . . yes C4 H4 0.960(3) . . yes C5 H5A 0.960(3) . . yes C5 H5B 0.961(2) . . yes C5 H5C 0.960(3) . . yes C7 H7 0.960(2) . . yes C8 H8 0.960(3) . . yes C10 H10 0.960(3) . . yes C11 H11 0.960(2) . . yes C13 H13A 0.960(3) . . yes C13 H13B 0.960(3) . . yes C13 H13C 0.960(3) . . yes C15 H15 0.960(2) . . yes C16 H16 0.961(2) . . yes C18 H18A 0.960(2) . . yes C18 H18B 0.960(2) . . yes C20 H20 0.960(3) . . yes C21 H21 0.960(2) . . yes C22 H22 0.960(2) . . yes C23 H23 0.960(3) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O12 C13 118.4(2) . . . yes O1 C2 O3 123.6(2) . . . yes O1 C2 C4 117.9(2) . . . yes O3 C2 C4 118.4(2) . . . yes C2 C4 C5 112.1(2) . . . yes C2 C4 C6 107.7(2) . . . yes C5 C4 C6 113.7(2) . . . yes C4 C6 C7 120.6(2) . . . yes C4 C6 C11 121.7(2) . . . yes C7 C6 C11 117.7(2) . . . yes C6 C7 C8 121.5(2) . . . yes C7 C8 C9 119.4(2) . . . yes O12 C9 C8 114.9(2) . . . yes O12 C9 C10 125.0(2) . . . yes C8 C9 C10 120.1(2) . . . yes C9 C10 C11 119.8(2) . . . yes C6 C11 C10 121.6(2) . . . yes N14 C15 C16 110.5(2) . . . yes N14 C15 C24 111.0(2) . . . yes C16 C15 C24 102.9(2) . . . yes O17 C16 C15 112.5(2) . . . yes O17 C16 C18 111.0(2) . . . yes C15 C16 C18 105.1(2) . . . yes C16 C18 C19 103.2(2) . . . yes C18 C19 C20 130.1(2) . . . yes C18 C19 C24 110.3(2) . . . yes C20 C19 C24 119.6(2) . . . yes C19 C20 C21 119.1(2) . . . yes C20 C21 C22 121.5(2) . . . yes C21 C22 C23 120.5(2) . . . yes C22 C23 C24 118.3(2) . . . yes C15 C24 C19 110.3(2) . . . yes C15 C24 C23 128.7(2) . . . yes C19 C24 C23 121.0(2) . . . yes C16 O17 H17 114.0(15) . . . yes H24A O24 H24B 124.7(39) . . . yes C15 N14 H14A 110.5(2) . . . yes C15 N14 H14B 108.0(2) . . . yes C15 N14 H14C 110.5(1) . . . yes H14A N14 H14B 109.4(2) . . . yes H14A N14 H14C 109.4(2) . . . yes H14B N14 H14C 109.0(2) . . . yes C2 C4 H4 108.6(2) . . . yes C5 C4 H4 107.0(2) . . . yes C6 C4 H4 107.5(2) . . . yes C4 C5 H5A 111.9(3) . . . yes C4 C5 H5B 110.6(2) . . . yes C4 C5 H5C 107.0(2) . . . yes H5A C5 H5B 109.1(2) . . . yes H5A C5 H5C 109.2(2) . . . yes H5B C5 H5C 109.1(3) . . . yes C6 C7 H7 119.1(2) . . . yes C8 C7 H7 119.4(2) . . . yes C7 C8 H8 120.6(3) . . . yes C9 C8 H8 120.0(2) . . . yes C9 C10 H10 119.2(2) . . . yes C11 C10 H10 121.0(3) . . . yes C6 C11 H11 118.2(2) . . . yes C10 C11 H11 120.2(2) . . . yes O12 C13 H13A 119.2(3) . . . yes O12 C13 H13B 108.0(3) . . . yes O12 C13 H13C 105.8(3) . . . yes H13A C13 H13B 107.2(3) . . . yes H13A C13 H13C 107.2(3) . . . yes H13B C13 H13C 109.0(4) . . . yes N14 C15 H15 108.0(2) . . . yes C16 C15 H15 108.8(2) . . . yes C24 C15 H15 115.5(2) . . . yes O17 C16 H16 109.2(2) . . . yes C15 C16 H16 109.3(2) . . . yes C18 C16 H16 109.7(2) . . . yes C16 C18 H18A 112.0(2) . . . yes C16 C18 H18B 110.0(2) . . . yes C19 C18 H18A 111.8(2) . . . yes C19 C18 H18B 110.6(2) . . . yes H18A C18 H18B 109.0(2) . . . yes C19 C20 H20 119.6(2) . . . yes C21 C20 H20 121.3(2) . . . yes C20 C21 H21 119.6(3) . . . yes C22 C21 H21 118.9(2) . . . yes C21 C22 H22 119.6(2) . . . yes C23 C22 H22 119.9(3) . . . yes C22 C23 H23 121.7(2) . . . yes C24 C23 H23 120.0(2) . . . yes #===END data_AI2 _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(R)-2-Phenylbutyric Acid ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(R)-4a ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chemistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japam ; _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _chemical_formula_moiety 'C19 H23 N1 O3 ' _chemical_formula_weight 313.00 _cell_length_a 12.351(3) _cell_length_b 6.170(2) _cell_length_c 11.431(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 99.10(2) _cell_angle_gamma 90.000000(0) _cell_volume 860.2(4) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_meas 1.208 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.653 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1895 _reflns_number_total 1474 _reflns_number_observed 1311 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_theta_max 51.41 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.043 _refine_ls_wR_factor_obs 0.047 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1311 _refine_ls_number_parameters 207 _refine_ls_goodness_of_fit_obs 1.050 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0284 _refine_ls_shift/esd_mean 0.0075 _refine_diff_density_min -0.21 _refine_diff_density_max 0.17 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 -0.00526 _diffrn_orient_matrix_UB_12 0.02029 _diffrn_orient_matrix_UB_13 0.08572 _diffrn_orient_matrix_UB_21 -0.06611 _diffrn_orient_matrix_UB_22 -0.09564 _diffrn_orient_matrix_UB_23 -0.00934 _diffrn_orient_matrix_UB_31 0.04823 _diffrn_orient_matrix_UB_32 -0.12927 _diffrn_orient_matrix_UB_33 0.02037 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,+Y+0.5,-Z _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O1 0.70342(9) -0.48060 0.08847(10) 0.0513(8) 1.000 Uij O16 0.43370(8) -0.72527(28) 0.04676(9) 0.0457(7) 1.000 Uij O3 0.78615(10) -0.19878(33) 0.18632(12) 0.0578(8) 1.000 Uij N13 0.63253(10) -0.90318(31) 0.12153(11) 0.0391(8) 1.000 Uij C2 0.78260(13) -0.39494(42) 0.15763(15) 0.043(1) 1.000 Uij C4 0.87603(13) -0.54085(36) 0.21194(15) 0.043(1) 1.000 Uij C5 0.87755(14) -0.55054(42) 0.34533(16) 0.056(1) 1.000 Uij C6 0.95602(18) -0.71725(50) 0.40821(19) 0.082(2) 1.000 Uij C7 0.98491(14) -0.47150(41) 0.17937(15) 0.044(1) 1.000 Uij C8 1.04401(17) -0.61190(44) 0.12025(18) 0.066(1) 1.000 Uij C9 1.1452(2) -0.5499(6) 0.0918(2) 0.086(2) 1.000 Uij C10 1.18717(18) -0.35147(69) 0.12075(22) 0.083(2) 1.000 Uij C11 1.12995(17) -0.20881(47) 0.17887(20) 0.071(2) 1.000 Uij C12 1.02913(15) -0.26822(44) 0.20895(18) 0.058(1) 1.000 Uij C14 0.55072(13) -0.93167(35) 0.20289(14) 0.039(1) 1.000 Uij C15 0.45271(12) -0.77833(37) 0.16808(15) 0.042(1) 1.000 Uij C17 0.47957(14) -0.57784(38) 0.24408(16) 0.049(1) 1.000 Uij C18 0.55542(13) -0.66125(37) 0.35116(15) 0.042(1) 1.000 Uij C19 0.58657(15) -0.56673(43) 0.46096(17) 0.058(1) 1.000 Uij C20 0.65929(16) -0.67528(49) 0.54488(16) 0.064(2) 1.000 Uij C21 0.70117(15) -0.87410(50) 0.52120(16) 0.062(1) 1.000 Uij C22 0.66937(14) -0.97017(40) 0.41151(16) 0.052(1) 1.000 Uij C23 0.59672(13) -0.86294(37) 0.32721(14) 0.041(1) 1.000 Uij H4 0.86123 -0.68615 0.18394 0.043 1.000 Uiso H5A 0.80455 -0.57894 0.36013 0.055 1.000 Uiso H5B 0.90055 -0.41114 0.37733 0.055 1.000 Uiso H6A 0.95672 -0.72025 0.49231 0.080 1.000 Uiso H6B 1.02902 -0.68885 0.39341 0.080 1.000 Uiso H6C 0.93302 -0.85665 0.37621 0.080 1.000 Uiso H8 1.01381 -0.75090 0.09535 0.065 1.000 Uiso H9 1.18856 -0.65040 0.05479 0.086 1.000 Uiso H10 1.25467 -0.30457 0.09735 0.083 1.000 Uiso H11 1.15975 -0.06871 0.20207 0.069 1.000 Uiso H12 0.98973 -0.16872 0.25125 0.057 1.000 Uiso H13A 0.60373 -0.94938 0.04253 0.038 1.000 Uiso H13B 0.69713 -0.98598 0.15033 0.038 1.000 Uiso H13C 0.65183 -0.75258 0.12023 0.038 1.000 Uiso H14 0.53082 -1.08197 0.20389 0.039 1.000 Uiso H15 0.38821 -0.84603 0.18848 0.041 1.000 Uiso H16 0.39120 -0.82546 -0.00604 0.045 1.000 Uiso H17A 0.41427 -0.51344 0.26448 0.049 1.000 Uiso H17B 0.51657 -0.47304 0.20248 0.049 1.000 Uiso H19 0.55777 -0.42683 0.47616 0.058 1.000 Uiso H20 0.681(5) -0.609(12) 0.621(5) 0.064 1.000 Uiso H21 0.74967 -0.95130 0.58080 0.061 1.000 Uiso H22 0.69837 -1.10717 0.39131 0.052 1.000 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 0.0429(6) 0.0452(8) 0.0615(8) 0.0000(7) -.0094(6) 0.0080(7) O16 0.0477(7) 0.0443(8) 0.0416(7) -.0056(6) -.0081(5) 0.0044(6) O3 0.0498(8) 0.0424(9) 0.0773(9) 0.0145(7) -.0045(6) -.0093(8) N13 0.0433(7) 0.0325(9) 0.0393(7) 0.0043(7) 0.0000(6) -.0031(7) C2 0.035(1) 0.047(1) 0.046(1) 0.006(1) 0.008(1) 0.006(1) C4 0.0379(9) 0.0361(11) 0.0538(11) 0.0047(9) -.0010(8) -.0010(10) C5 0.048(1) 0.061(1) 0.057(1) -0.002(1) 0.001(1) 0.008(1) C6 0.082(1) 0.084(2) 0.073(1) 0.011(2) -0.009(1) 0.029(2) C7 0.0382(9) 0.0506(12) 0.0424(10) 0.0092(10) -.0013(8) 0.0003(10) C8 0.059(1) 0.072(2) 0.062(1) 0.019(1) 0.003(1) -0.014(1) C9 0.058(2) 0.128(3) 0.071(2) 0.028(2) 0.019(1) -0.008(2) C10 0.049(1) 0.128(3) 0.073(2) 0.007(2) 0.015(1) 0.023(2) C11 0.051(1) 0.074(2) 0.084(2) -0.008(1) -0.005(1) 0.019(2) C12 0.042(1) 0.059(1) 0.070(1) 0.003(1) 0.008(1) 0.002(1) C14 0.0442(9) 0.0307(10) 0.0422(9) -.0017(9) 0.0066(8) 0.0025(8) C15 0.0368(9) 0.0433(11) 0.0439(10) -.0011(9) 0.0048(8) 0.0067(9) C17 0.052(1) 0.043(1) 0.050(1) 0.008(1) 0.009(1) -0.002(1) C18 0.041(1) 0.045(1) 0.039(1) -0.001(1) 0.008(1) 0.000(1) C19 0.062(1) 0.062(1) 0.050(1) 0.000(1) 0.017(1) -0.009(1) C20 0.060(1) 0.092(2) 0.041(1) -0.010(1) 0.005(1) -0.009(1) C21 0.054(1) 0.087(2) 0.042(1) 0.002(1) 0.004(1) 0.012(1) C22 0.053(1) 0.054(1) 0.049(1) 0.007(1) 0.008(1) 0.010(1) C23 0.0406(9) 0.0433(12) 0.0375(9) 0.0014(9) 0.0075(8) 0.0060(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.271(3) . . yes O16 C15 1.408(3) . . yes O3 C2 1.253(4) . . yes N13 C14 1.488(3) . . yes C2 C4 1.517(3) . . yes C4 C5 1.523(3) . . yes C4 C7 1.513(3) . . yes C5 C6 1.514(4) . . yes C7 C8 1.377(4) . . yes C7 C12 1.388(4) . . yes C8 C9 1.393(4) . . yes C9 C10 1.350(6) . . yes C10 C11 1.365(5) . . yes C11 C12 1.392(3) . . yes C14 C15 1.538(3) . . yes C14 C23 1.506(3) . . yes C15 C17 1.518(4) . . yes C17 C18 1.509(3) . . yes C18 C19 1.382(3) . . yes C18 C23 1.389(4) . . yes C19 C20 1.379(4) . . yes C20 C21 1.375(5) . . yes C21 C22 1.386(3) . . yes C22 C23 1.378(3) . . yes O16 H16 0.960(2) . . yes N13 H13A 0.960(2) . . yes N13 H13B 0.961(2) . . yes N13 H13C 0.960(2) . . yes C4 H4 0.960(3) . . yes C5 H5A 0.959(2) . . yes C5 H5B 0.960(3) . . yes C6 H6A 0.960(3) . . yes C6 H6B 0.959(3) . . yes C6 H6C 0.960(3) . . yes C8 H8 0.960(3) . . yes C9 H9 0.960(4) . . yes C10 H10 0.960(3) . . yes C11 H11 0.960(3) . . yes C12 H12 0.960(3) . . yes C14 H14 0.960(3) . . yes C15 H15 0.960(2) . . yes C17 H17A 0.960(2) . . yes C17 H17B 0.960(3) . . yes C19 H19 0.960(3) . . yes C20 H20 0.96(7) . . yes C21 H21 0.960(3) . . yes C22 H22 0.960(3) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 123.8(2) . . . yes O1 C2 C4 117.9(2) . . . yes O3 C2 C4 118.3(2) . . . yes C2 C4 C5 108.7(2) . . . yes C2 C4 C7 112.3(2) . . . yes C5 C4 C7 112.8(2) . . . yes C4 C5 C6 114.0(2) . . . yes C4 C7 C8 120.2(3) . . . yes C4 C7 C12 121.8(2) . . . yes C8 C7 C12 118.0(2) . . . yes C7 C8 C9 120.4(3) . . . yes C8 C9 C10 121.0(3) . . . yes C9 C10 C11 119.7(3) . . . yes C10 C11 C12 120.2(3) . . . yes C7 C12 C11 120.7(3) . . . yes N13 C14 C15 110.5(2) . . . yes N13 C14 C23 111.4(2) . . . yes C15 C14 C23 103.6(2) . . . yes O16 C15 C14 113.5(2) . . . yes O16 C15 C17 111.2(2) . . . yes C14 C15 C17 105.2(2) . . . yes C15 C17 C18 103.8(2) . . . yes C17 C18 C19 129.8(3) . . . yes C17 C18 C23 110.2(2) . . . yes C19 C18 C23 119.9(2) . . . yes C18 C19 C20 118.9(3) . . . yes C19 C20 C21 121.3(2) . . . yes C20 C21 C22 119.9(2) . . . yes C21 C22 C23 119.2(3) . . . yes C14 C23 C18 110.1(2) . . . yes C14 C23 C22 129.2(2) . . . yes C18 C23 C22 120.8(2) . . . yes C15 O16 H16 117.3(2) . . . yes C14 N13 H13A 111.4(2) . . . yes C14 N13 H13B 109.4(2) . . . yes C14 N13 H13C 108.6(2) . . . yes H13A N13 H13B 109.2(2) . . . yes H13A N13 H13C 109.2(2) . . . yes H13B N13 H13C 109.0(2) . . . yes C2 C4 H4 109.0(2) . . . yes C5 C4 H4 105.6(2) . . . yes C7 C4 H4 108.2(2) . . . yes C4 C5 H5A 108.7(2) . . . yes C4 C5 H5B 107.6(2) . . . yes C6 C5 H5A 109.9(3) . . . yes C6 C5 H5B 107.4(2) . . . yes H5A C5 H5B 109.0(3) . . . yes C5 C6 H6A 113.1(3) . . . yes C5 C6 H6B 109.9(3) . . . yes C5 C6 H6C 107.4(2) . . . yes H6A C6 H6B 108.7(3) . . . yes H6A C6 H6C 108.6(3) . . . yes H6B C6 H6C 109.0(3) . . . yes C7 C8 H8 119.7(3) . . . yes C9 C8 H8 119.8(3) . . . yes C8 C9 H9 120.6(4) . . . yes C10 C9 H9 118.3(3) . . . yes C9 C10 H10 121.5(4) . . . yes C11 C10 H10 118.7(4) . . . yes C10 C11 H11 120.6(3) . . . yes C12 C11 H11 119.2(3) . . . yes C7 C12 H12 119.3(2) . . . yes C11 C12 H12 120.0(3) . . . yes N13 C14 H14 108.8(2) . . . yes C15 C14 H14 113.9(2) . . . yes C23 C14 H14 108.7(2) . . . yes O16 C15 H15 109.0(2) . . . yes C14 C15 H15 108.6(2) . . . yes C17 C15 H15 109.3(2) . . . yes C15 C17 H17A 111.1(2) . . . yes C15 C17 H17B 110.1(2) . . . yes C18 C17 H17A 112.4(2) . . . yes C18 C17 H17B 110.4(2) . . . yes H17A C17 H17B 109.0(3) . . . yes C18 C19 H19 119.1(2) . . . yes C20 C19 H19 122.0(3) . . . yes C19 C20 H20 118.6(42) . . . yes C21 C20 H20 120.1(42) . . . yes C20 C21 H21 121.0(3) . . . yes C22 C21 H21 119.1(3) . . . yes C21 C22 H22 122.1(3) . . . yes C23 C22 H22 118.7(2) . . . yes #===END data_AI2-inv _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(S)-2-Phenylbutyric Acid ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(S)-4a. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chemistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japan ; _chemical_compound_source 'Saigol laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _chemical_formula_moiety 'C19 H23 N1 O3 ' _chemical_formula_weight 313.00 _cell_length_a 16.848(4) _cell_length_b 5.947(2) _cell_length_c 8.580(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 101.75(2) _cell_angle_gamma 90.000000(0) _cell_volume 841.7(4) _cell_measurement_reflns_used '30' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_meas 1.235 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.667 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1612 _reflns_number_total 1466 _reflns_number_observed 1387 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_theta_max 51.24 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.101 _refine_ls_wR_factor_obs 0.132 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1387 _refine_ls_number_parameters 207 _refine_ls_goodness_of_fit_obs 1.767 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0111 _refine_ls_shift/esd_mean 0.0030 _refine_diff_density_min -0.57 _refine_diff_density_max 0.48 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 -0.04682 _diffrn_orient_matrix_UB_12 0.08989 _diffrn_orient_matrix_UB_13 0.02124 _diffrn_orient_matrix_UB_21 0.03097 _diffrn_orient_matrix_UB_22 0.03395 _diffrn_orient_matrix_UB_23 0.10977 _diffrn_orient_matrix_UB_31 0.02291 _diffrn_orient_matrix_UB_32 0.13799 _diffrn_orient_matrix_UB_33 -0.04087 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,+Y+0.5,-Z _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O1 -0.2413(2) 0.5060 -0.0757(5) 0.047(2) 1.000 Uij O3 -0.1571(2) 0.2215(9) -0.0625(5) 0.046(2) 1.000 Uij O16 0.03123(19) -0.03843(91) -0.10319(39) 0.041(2) 1.000 Uij N13 -0.1171(2) -0.2253(9) -0.1044(5) 0.033(2) 1.000 Uij C2 -0.2276(3) 0.3084(11) -0.0832(6) 0.032(2) 1.000 Uij C4 -0.2977(3) 0.1432(12) -0.1264(6) 0.037(2) 1.000 Uij C5 -0.3566(3) 0.1694(14) -0.0108(7) 0.051(3) 1.000 Uij C6 -0.4216(4) -0.0138(20) -0.0352(8) 0.084(5) 1.000 Uij C7 -0.3408(3) 0.1783(11) -0.2988(6) 0.038(3) 1.000 Uij C8 -0.3847(3) 0.3662(13) -0.3495(6) 0.048(3) 1.000 Uij C9 -0.4226(4) 0.3935(15) -0.5080(7) 0.059(4) 1.000 Uij C10 -0.4164(3) 0.2309(16) -0.6161(7) 0.057(4) 1.000 Uij C11 -0.3736(4) 0.0446(15) -0.5695(7) 0.058(4) 1.000 Uij C12 -0.3361(3) 0.0139(14) -0.4090(7) 0.050(3) 1.000 Uij C14 -0.0748(3) -0.3036(10) -0.2328(5) 0.035(2) 1.000 Uij C15 -0.0072(3) -0.1401(12) -0.2480(6) 0.039(3) 1.000 Uij C17 -0.0488(3) 0.0368(12) -0.3686(6) 0.044(3) 1.000 Uij C18 -0.1123(3) -0.1037(12) -0.4736(6) 0.038(3) 1.000 Uij C19 -0.1529(3) -0.0702(16) -0.6320(6) 0.058(4) 1.000 Uij C20 -0.2049(4) -0.2283(17) -0.7074(6) 0.061(4) 1.000 Uij C21 -0.2202(4) -0.4192(14) -0.6275(8) 0.056(3) 1.000 Uij C22 -0.1830(3) -0.4537(11) -0.4701(6) 0.044(3) 1.000 Uij C23 -0.1289(3) -0.2985(11) -0.3967(5) 0.036(3) 1.000 Uij H4 -0.27743 -0.00779 -0.11189 0.036 1.000 Uiso H5A -0.32627 0.15993 0.09663 0.050 1.000 Uiso H5B -0.38217 0.31413 -0.02677 0.050 1.000 Uiso H6A -0.45812 0.00232 0.03660 0.084 1.000 Uiso H6B -0.45192 -0.00428 -0.14260 0.084 1.000 Uiso H6C -0.39602 -0.15848 -0.01920 0.084 1.000 Uiso H8 -0.38949 0.47941 -0.27218 0.047 1.000 Uiso H9 -0.45288 0.52817 -0.54001 0.057 1.000 Uiso H10 -0.44163 0.25022 -0.72609 0.055 1.000 Uiso H11 -0.36851 -0.07104 -0.64493 0.057 1.000 Uiso H12 -0.30706 -0.12214 -0.37441 0.049 1.000 Uiso H13A -0.08300 -0.23055 -0.00015 0.032 1.000 Uiso H13B -0.13460 -0.07305 -0.12755 0.032 1.000 Uiso H13C -0.16380 -0.31835 -0.10545 0.032 1.000 Uiso H14 -0.05726 -0.45579 -0.20957 0.034 1.000 Uiso H15 0.03360 -0.22243 -0.28744 0.038 1.000 Uiso H16 0.05323 -0.15233 -0.02729 0.039 1.000 Uiso H17A -0.01203 0.10340 -0.42708 0.042 1.000 Uiso H17B -0.07313 0.15370 -0.31688 0.042 1.000 Uiso H19 -0.14255 0.06403 -0.68669 0.057 1.000 Uiso H20 -0.23198 -0.20729 -0.81625 0.060 1.000 Uiso H21 -0.25738 -0.52966 -0.68153 0.054 1.000 Uiso H22 -0.19481 -0.58486 -0.41366 0.042 1.000 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 0.040(2) 0.020(2) 0.076(3) -0.007(2) 0.002(2) -0.003(2) O3 0.034(2) 0.024(2) 0.074(2) 0.006(2) -0.005(2) -0.012(2) O16 0.037(2) 0.038(2) 0.043(2) 0.003(2) -0.010(1) -0.009(2) N13 0.032(2) 0.022(2) 0.041(2) -0.002(2) -0.006(2) 0.002(2) C2 0.035(2) 0.025(3) 0.035(2) -0.004(2) 0.001(2) -0.006(2) C4 0.038(2) 0.026(3) 0.043(3) 0.003(2) -0.005(2) 0.002(2) C5 0.041(3) 0.064(4) 0.045(3) -0.007(3) 0.001(2) 0.000(3) C6 0.069(4) 0.115(7) 0.066(4) -0.047(5) 0.022(3) -0.025(5) C7 0.030(2) 0.039(3) 0.042(3) -0.011(2) 0.001(2) -0.001(2) C8 0.045(3) 0.046(4) 0.049(3) 0.004(3) 0.004(2) -0.002(3) C9 0.055(3) 0.061(4) 0.056(3) 0.007(3) -0.002(3) 0.011(3) C10 0.051(3) 0.072(5) 0.043(3) 0.001(4) -0.001(2) 0.001(3) C11 0.057(3) 0.070(5) 0.044(3) -0.001(4) 0.008(2) -0.013(3) C12 0.044(3) 0.049(4) 0.053(3) 0.010(3) -0.001(2) -0.006(3) C14 0.041(2) 0.024(3) 0.036(2) 0.010(2) -0.007(2) -0.006(2) C15 0.027(2) 0.041(3) 0.044(3) 0.004(2) -0.003(2) -0.010(2) C17 0.043(3) 0.035(3) 0.049(3) -0.005(3) -0.001(2) -0.002(2) C18 0.032(2) 0.038(3) 0.040(2) 0.003(2) 0.001(2) 0.004(2) C19 0.051(3) 0.081(5) 0.039(3) -0.006(3) 0.000(2) 0.008(3) C20 0.051(3) 0.094(6) 0.033(3) 0.005(4) -0.008(2) -0.003(3) C21 0.050(3) 0.060(4) 0.052(3) -0.004(3) -0.010(3) -0.017(3) C22 0.053(3) 0.032(3) 0.043(3) 0.003(3) 0.001(2) -0.004(2) C23 0.038(2) 0.033(3) 0.034(2) 0.012(2) -0.002(2) -0.007(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.202(7) . . yes O3 C2 1.273(7) . . yes O16 C15 1.415(7) . . yes N13 C14 1.503(7) . . yes C2 C4 1.524(8) . . yes C4 C5 1.546(8) . . yes C4 C7 1.523(7) . . yes C5 C6 1.529(13) . . yes C7 C8 1.362(10) . . yes C7 C12 1.374(10) . . yes C8 C9 1.389(8) . . yes C9 C10 1.358(11) . . yes C10 C11 1.338(12) . . yes C11 C12 1.406(9) . . yes C14 C15 1.523(8) . . yes C14 C23 1.513(7) . . yes C15 C17 1.541(9) . . yes C17 C18 1.504(8) . . yes C18 C19 1.405(8) . . yes C18 C23 1.390(9) . . yes C19 C20 1.357(12) . . yes C20 C21 1.377(12) . . yes C21 C22 1.384(9) . . yes C22 C23 1.358(9) . . yes O16 H16 0.960(5) . . yes N13 H13A 0.960(4) . . yes N13 H13B 0.960(6) . . yes N13 H13C 0.961(5) . . yes C4 H4 0.960(7) . . yes C5 H5A 0.960(6) . . yes C5 H5B 0.960(8) . . yes C6 H6A 0.960(7) . . yes C6 H6B 0.960(7) . . yes C6 H6C 0.960(12) . . yes C8 H8 0.960(7) . . yes C9 H9 0.959(9) . . yes C10 H10 0.960(6) . . yes C11 H11 0.960(8) . . yes C12 H12 0.960(8) . . yes C14 H14 0.960(6) . . yes C15 H15 0.960(6) . . yes C17 H17A 0.959(6) . . yes C17 H17B 0.960(7) . . yes C19 H19 0.959(9) . . yes C20 H20 0.960(6) . . yes C21 H21 0.960(8) . . yes C22 H22 0.960(7) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 125.0(6) . . . yes O1 C2 C4 119.6(5) . . . yes O3 C2 C4 115.3(6) . . . yes C2 C4 C5 110.2(5) . . . yes C2 C4 C7 109.9(5) . . . yes C5 C4 C7 111.6(5) . . . yes C4 C5 C6 112.0(6) . . . yes C4 C7 C8 122.9(6) . . . yes C4 C7 C12 119.2(6) . . . yes C8 C7 C12 117.9(5) . . . yes C7 C8 C9 121.3(7) . . . yes C8 C9 C10 120.1(8) . . . yes C9 C10 C11 119.8(6) . . . yes C10 C11 C12 120.5(7) . . . yes C7 C12 C11 120.3(7) . . . yes N13 C14 C15 109.9(5) . . . yes N13 C14 C23 112.9(4) . . . yes C15 C14 C23 103.1(5) . . . yes O16 C15 C14 114.4(4) . . . yes O16 C15 C17 111.2(6) . . . yes C14 C15 C17 104.3(4) . . . yes C15 C17 C18 101.2(6) . . . yes C17 C18 C19 130.3(7) . . . yes C17 C18 C23 111.5(5) . . . yes C19 C18 C23 118.2(6) . . . yes C18 C19 C20 120.2(8) . . . yes C19 C20 C21 120.1(6) . . . yes C20 C21 C22 121.0(7) . . . yes C21 C22 C23 118.6(6) . . . yes C14 C23 C18 108.5(5) . . . yes C14 C23 C22 129.6(6) . . . yes C18 C23 C22 121.8(5) . . . yes C15 O16 H16 109.8(6) . . . yes C14 N13 H13A 112.9(4) . . . yes C14 N13 H13B 108.2(4) . . . yes C14 N13 H13C 108.9(5) . . . yes H13A N13 H13B 108.9(5) . . . yes H13A N13 H13C 108.9(5) . . . yes H13B N13 H13C 109.0(4) . . . yes C2 C4 H4 109.5(5) . . . yes C5 C4 H4 105.6(6) . . . yes C7 C4 H4 109.9(6) . . . yes C4 C5 H5A 109.0(5) . . . yes C4 C5 H5B 109.1(6) . . . yes C6 C5 H5A 108.4(7) . . . yes C6 C5 H5B 109.3(6) . . . yes H5A C5 H5B 109.0(7) . . . yes C5 C6 H6A 112.1(9) . . . yes C5 C6 H6B 108.4(9) . . . yes C5 C6 H6C 109.3(7) . . . yes H6A C6 H6B 109.0(7) . . . yes H6A C6 H6C 109.0(10) . . . yes H6B C6 H6C 109.0(10) . . . yes C7 C8 H8 118.1(6) . . . yes C9 C8 H8 120.5(7) . . . yes C8 C9 H9 119.3(8) . . . yes C10 C9 H9 120.6(6) . . . yes C9 C10 H10 120.4(9) . . . yes C11 C10 H10 119.8(8) . . . yes C10 C11 H11 120.6(6) . . . yes C12 C11 H11 118.9(8) . . . yes C7 C12 H12 118.9(6) . . . yes C11 C12 H12 120.8(7) . . . yes N13 C14 H14 108.2(5) . . . yes C15 C14 H14 114.6(5) . . . yes C23 C14 H14 108.3(5) . . . yes O16 C15 H15 107.2(4) . . . yes C14 C15 H15 107.8(6) . . . yes C17 C15 H15 111.9(5) . . . yes C15 C17 H17A 112.3(5) . . . yes C15 C17 H17B 111.3(5) . . . yes C18 C17 H17A 111.9(5) . . . yes C18 C17 H17B 111.1(5) . . . yes H17A C17 H17B 108.9(7) . . . yes C18 C19 H19 119.4(7) . . . yes C20 C19 H19 120.4(6) . . . yes C19 C20 H20 120.5(9) . . . yes C21 C20 H20 119.4(8) . . . yes C20 C21 H21 119.6(7) . . . yes C22 C21 H21 119.4(8) . . . yes C21 C22 H22 120.9(7) . . . yes C23 C22 H22 120.5(6) . . . yes #===END data_(1S,2R)-2/(R)-4b _publ_section_title ; Crystal and molecular structure of (R)-2-(p-tolyl)-butyric acid & (1S,2R)-AI ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(R)-4b. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 2 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _chemical_formula_moiety 'C20 H25 N1 O3 ' _chemical_formula_weight 327.00 _cell_length_a 17.045(4) _cell_length_b 6.148(2) _cell_length_c 17.931(4) _cell_angle_alpha 90.000000(0) _cell_angle_beta 101.22(2) _cell_angle_gamma 90.000000(0) _cell_volume 1843.1(9) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1' _cell_measurement_theta_max '30' _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_meas 1.178 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.629 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'numerical (from crystal size)' _diffrn_reflns_number 1799 _reflns_number_total 1648 _reflns_number_observed 1571 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_theta_max 51.41 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.049 _refine_ls_wR_factor_obs 0.052 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1571 _refine_ls_number_parameters 219 _refine_ls_goodness_of_fit_obs 1.252 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.1826 _refine_ls_shift/esd_mean 0.0244 _refine_diff_density_min -0.26 _refine_diff_density_max 0.14 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 -0.01869 _diffrn_orient_matrix_UB_12 0.02324 _diffrn_orient_matrix_UB_13 0.05094 _diffrn_orient_matrix_UB_21 0.05244 _diffrn_orient_matrix_UB_22 -0.02639 _diffrn_orient_matrix_UB_23 0.03126 _diffrn_orient_matrix_UB_31 0.01153 _diffrn_orient_matrix_UB_32 0.15881 _diffrn_orient_matrix_UB_33 -0.00225 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z +X,+Y+0.5,+Z+0.5 -X,+Y,-Z -X,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'C 2 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O3 -0.27321(18) -0.27600 -0.15113(16) 0.044(2) 1.000 Uij O17 -0.28787(20) -0.01861(80) 0.03053(16) 0.043(2) 1.000 Uij O1 -0.31310(22) -0.56121(82) -0.22583(18) 0.055(2) 1.000 Uij N14 -0.30006(20) 0.14780(82) -0.11175(18) 0.036(2) 1.000 Uij C15 -0.3708(3) 0.1790(9) -0.0761(2) 0.037(2) 1.000 Uij C7 -0.2756(3) -0.1849(10) -0.3306(2) 0.037(2) 1.000 Uij C24 -0.4478(3) 0.1094(10) -0.1281(3) 0.043(3) 1.000 Uij C4 -0.3372(3) -0.2045(10) -0.2798(2) 0.042(3) 1.000 Uij C19 -0.4696(3) -0.0964(10) -0.1082(3) 0.042(3) 1.000 Uij C18 -0.4086(3) -0.1840(10) -0.0420(3) 0.044(3) 1.000 Uij C8 -0.2578(3) -0.3579(11) -0.3733(3) 0.046(3) 1.000 Uij C9 -0.2010(3) -0.3360(11) -0.4196(3) 0.051(3) 1.000 Uij C16 -0.3674(3) 0.0248(10) -0.0075(2) 0.038(2) 1.000 Uij C13 -0.2365(3) 0.0095(11) -0.3341(3) 0.050(3) 1.000 Uij C2 -0.3055(3) -0.3620(10) -0.2140(3) 0.041(3) 1.000 Uij C10 -0.1607(3) -0.1423(12) -0.4228(3) 0.053(3) 1.000 Uij C20 -0.5402(3) -0.1914(12) -0.1468(3) 0.060(4) 1.000 Uij C23 -0.4936(3) 0.2267(12) -0.1867(3) 0.061(3) 1.000 Uij C5 -0.4201(3) -0.2730(12) -0.3233(3) 0.057(3) 1.000 Uij C21 -0.5873(3) -0.0689(17) -0.2052(3) 0.072(4) 1.000 Uij C11 -0.0977(3) -0.1226(14) -0.4715(3) 0.079(4) 1.000 Uij C12 -0.1785(3) 0.0286(12) -0.3801(3) 0.061(4) 1.000 Uij C22 -0.5647(3) 0.1321(16) -0.2250(3) 0.078(5) 1.000 Uij C6 -0.4557(3) -0.1052(14) -0.3832(3) 0.076(4) 1.000 Uij H11A -0.06980 0.01205 -0.47399 0.086 1.000 Uiso H11B -0.12140 -0.15945 -0.52299 0.086 1.000 Uiso H11C -0.05750 -0.22845 -0.45199 0.086 1.000 Uiso H12 -0.15120 0.16470 -0.38159 0.066 1.000 Uiso H13 -0.24875 0.13207 -0.30531 0.054 1.000 Uiso H9 -0.18966 -0.45756 -0.44938 0.053 1.000 Uiso H8 -0.28385 -0.49538 -0.37109 0.052 1.000 Uiso H5A -0.45547 -0.29139 -0.28819 0.061 1.000 Uiso H5B -0.41507 -0.40919 -0.34809 0.061 1.000 Uiso H6A -0.50738 -0.14787 -0.41095 0.080 1.000 Uiso H6B -0.42028 -0.08677 -0.41835 0.080 1.000 Uiso H6C -0.46068 0.03103 -0.35845 0.080 1.000 Uiso H4 -0.34703 -0.06407 -0.26011 0.047 1.000 Uiso H14A -0.25156 0.19350 -0.07875 0.040 1.000 Uiso H14B -0.30716 0.23150 -0.15775 0.040 1.000 Uiso H14C -0.29536 -0.00310 -0.12385 0.040 1.000 Uiso H16 -0.39667 0.09012 0.02732 0.042 1.000 Uiso H15 -0.37547 0.32989 -0.06399 0.042 1.000 Uiso H18A -0.37087 -0.27842 -0.05907 0.047 1.000 Uiso H18B -0.43347 -0.26112 -0.00617 0.047 1.000 Uiso H23 -0.47548 0.36512 -0.20150 0.066 1.000 Uiso H22 -0.59942 0.21651 -0.26274 0.078 1.000 Uiso H21 -0.63574 -0.13120 -0.23353 0.079 1.000 Uiso H20 -0.55771 -0.33144 -0.13293 0.065 1.000 Uiso H17 -0.274(3) 0.051(10) 0.054(3) 0.046(9) 1.000 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 O3 0.056(2) 0.042(2) 0.031(2) 0.010(2) -0.002(1) -0.002(2) O17 0.045(2) 0.046(2) 0.034(2) 0.009(2) -0.009(1) -0.003(2) O1 0.081(3) 0.042(2) 0.037(2) -0.003(2) 0.002(2) 0.004(2) N14 0.039(2) 0.033(2) 0.031(2) -0.005(2) -0.003(1) 0.002(2) C15 0.041(2) 0.029(3) 0.037(2) 0.003(2) -0.004(2) -0.003(2) C7 0.042(2) 0.042(3) 0.026(2) -0.001(2) -0.001(2) 0.006(2) C24 0.037(2) 0.050(3) 0.039(2) 0.005(2) -0.004(2) -0.005(2) C4 0.051(3) 0.044(3) 0.031(2) 0.004(2) 0.006(2) 0.006(2) C19 0.036(2) 0.048(3) 0.039(3) -0.001(2) 0.004(2) -0.011(2) C18 0.045(3) 0.037(3) 0.048(3) -0.001(2) 0.011(2) 0.002(2) C8 0.051(3) 0.044(3) 0.040(2) -0.005(3) 0.002(2) -0.003(3) C9 0.059(3) 0.053(3) 0.038(2) 0.011(3) 0.009(2) -0.002(3) C16 0.039(2) 0.041(3) 0.032(2) 0.008(2) 0.000(2) -0.004(2) C13 0.063(3) 0.040(3) 0.047(3) -0.002(3) 0.013(2) -0.001(3) C2 0.043(2) 0.044(3) 0.035(2) 0.004(2) 0.011(2) 0.007(2) C10 0.051(3) 0.068(4) 0.037(3) 0.010(3) 0.009(2) 0.014(3) C20 0.049(3) 0.070(4) 0.060(3) -0.015(3) 0.014(2) -0.021(3) C23 0.056(3) 0.067(4) 0.054(3) 0.012(3) -0.007(3) 0.008(3) C5 0.045(3) 0.074(4) 0.049(3) 0.003(3) 0.007(2) 0.016(3) C21 0.042(3) 0.114(6) 0.056(3) -0.009(4) -0.005(3) -0.022(4) C11 0.063(3) 0.102(6) 0.073(4) 0.011(4) 0.031(3) 0.027(4) C12 0.065(3) 0.050(3) 0.065(3) -0.010(3) 0.016(3) 0.011(3) C22 0.051(3) 0.115(7) 0.060(4) 0.017(4) -0.016(3) -0.001(4) C6 0.064(3) 0.096(6) 0.062(3) 0.015(4) -0.006(3) 0.025(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C2 1.270(6) . . yes O17 C16 1.419(6) . . yes O1 C2 1.245(8) . . yes N14 C15 1.483(6) . . yes C15 C24 1.517(7) . . yes C15 C16 1.545(7) . . yes C7 C4 1.523(6) . . yes C7 C8 1.378(8) . . yes C7 C13 1.376(9) . . yes C24 C19 1.385(9) . . yes C24 C23 1.383(8) . . yes C4 C2 1.541(8) . . yes C4 C5 1.533(7) . . yes C19 C18 1.517(7) . . yes C19 C20 1.395(8) . . yes C18 C16 1.535(9) . . yes C8 C9 1.399(7) . . yes C9 C10 1.381(10) . . yes C13 C12 1.409(8) . . yes C10 C11 1.516(8) . . yes C10 C12 1.368(10) . . yes C20 C21 1.408(10) . . yes C23 C22 1.399(9) . . yes C5 C6 1.528(10) . . yes C21 C22 1.362(14) . . yes O17 H17 0.62(6) . . yes N14 H14A 0.960(4) . . yes N14 H14B 0.960(4) . . yes N14 H14C 0.960(5) . . yes C15 H15 0.960(6) . . yes C4 H4 0.960(6) . . yes C18 H18A 0.959(6) . . yes C18 H18B 0.961(6) . . yes C8 H8 0.960(7) . . yes C9 H9 0.960(7) . . yes C16 H16 0.960(5) . . yes C13 H13 0.960(6) . . yes C20 H20 0.960(8) . . yes C23 H23 0.960(8) . . yes C5 H5A 0.960(5) . . yes C5 H5B 0.960(7) . . yes C21 H21 0.960(7) . . yes C11 H11A 0.960(9) . . yes C11 H11B 0.960(7) . . yes C11 H11C 0.960(8) . . yes C12 H12 0.960(7) . . yes C22 H22 0.960(8) . . yes C6 H6A 0.960(6) . . yes C6 H6B 0.960(6) . . yes C6 H6C 0.960(8) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N14 C15 C24 112.2(4) . . . yes N14 C15 C16 110.9(4) . . . yes C24 C15 C16 102.2(4) . . . yes C4 C7 C8 121.6(6) . . . yes C4 C7 C13 119.5(5) . . . yes C8 C7 C13 118.9(5) . . . yes C15 C24 C19 110.0(5) . . . yes C15 C24 C23 127.8(6) . . . yes C19 C24 C23 122.2(5) . . . yes C7 C4 C2 109.1(4) . . . yes C7 C4 C5 113.1(4) . . . yes C2 C4 C5 111.6(5) . . . yes C24 C19 C18 110.4(5) . . . yes C24 C19 C20 120.2(5) . . . yes C18 C19 C20 129.4(6) . . . yes C19 C18 C16 102.0(5) . . . yes C7 C8 C9 120.5(6) . . . yes C8 C9 C10 120.9(6) . . . yes O17 C16 C15 112.5(4) . . . yes O17 C16 C18 110.8(5) . . . yes C15 C16 C18 104.4(4) . . . yes C7 C13 C12 120.0(6) . . . yes O3 C2 O1 125.0(5) . . . yes O3 C2 C4 116.4(5) . . . yes O1 C2 C4 118.6(5) . . . yes C9 C10 C11 120.4(6) . . . yes C9 C10 C12 118.3(5) . . . yes C11 C10 C12 121.3(7) . . . yes C19 C20 C21 117.2(7) . . . yes C24 C23 C22 117.6(7) . . . yes C4 C5 C6 111.9(6) . . . yes C20 C21 C22 122.0(6) . . . yes C13 C12 C10 121.3(6) . . . yes C23 C22 C21 120.8(7) . . . yes C16 O17 H17 114.0(52) . . . yes C15 N14 H14A 111.8(4) . . . yes C15 N14 H14B 108.9(4) . . . yes C15 N14 H14C 109.5(4) . . . yes H14A N14 H14B 108.8(5) . . . yes H14A N14 H14C 108.8(4) . . . yes H14B N14 H14C 109.0(4) . . . yes N14 C15 H15 109.5(5) . . . yes C24 C15 H15 108.1(5) . . . yes C16 C15 H15 113.9(4) . . . yes C7 C4 H4 109.8(6) . . . yes C2 C4 H4 110.1(4) . . . yes C5 C4 H4 103.0(5) . . . yes C19 C18 H18A 111.4(5) . . . yes C19 C18 H18B 111.9(5) . . . yes C16 C18 H18A 110.6(5) . . . yes C16 C18 H18B 111.7(5) . . . yes H18A C18 H18B 109.0(6) . . . yes C7 C8 H8 120.2(5) . . . yes C9 C8 H8 119.3(6) . . . yes C8 C9 H9 119.5(7) . . . yes C10 C9 H9 119.6(5) . . . yes O17 C16 H16 109.6(4) . . . yes C15 C16 H16 108.5(6) . . . yes C18 C16 H16 110.9(5) . . . yes C7 C13 H13 119.9(5) . . . yes C12 C13 H13 120.0(7) . . . yes C19 C20 H20 121.9(6) . . . yes C21 C20 H20 120.8(6) . . . yes C24 C23 H23 120.5(6) . . . yes C22 C23 H23 121.8(7) . . . yes C4 C5 H5A 109.5(5) . . . yes C4 C5 H5B 108.6(5) . . . yes C6 C5 H5A 109.1(6) . . . yes C6 C5 H5B 108.8(5) . . . yes H5A C5 H5B 109.0(7) . . . yes C20 C21 H21 119.1(9) . . . yes C22 C21 H21 118.8(8) . . . yes C10 C11 H11A 120.6(7) . . . yes C10 C11 H11B 108.8(6) . . . yes C10 C11 H11C 105.7(6) . . . yes H11A C11 H11B 106.2(7) . . . yes H11A C11 H11C 106.1(6) . . . yes H11B C11 H11C 109.1(8) . . . yes C13 C12 H12 119.2(7) . . . yes C10 C12 H12 119.5(6) . . . yes C23 C22 H22 118.6(9) . . . yes C21 C22 H22 120.5(7) . . . yes C5 C6 H6A 112.2(7) . . . yes C5 C6 H6B 109.1(6) . . . yes C5 C6 H6C 108.8(6) . . . yes H6A C6 H6B 108.9(6) . . . yes H6A C6 H6C 108.8(7) . . . yes H6B C6 H6C 109.0(8) . . . yes #==END data_AIip _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(S)-3-Methyl-2-Phenylbutyric Acid ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(S)-6 ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chemistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japan ; _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _chemical_formula_moiety 'C20 H24 N1 O3 ' _chemical_formula_weight 326.00 _cell_length_a 19.831(2) _cell_length_b 5.786(1) _cell_length_c 16.453(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 110.57(1) _cell_angle_gamma 90.000000(0) _cell_volume 1767.7(5) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_meas 1.224 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.656 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'numerical (from crystal size)' _diffrn_reflns_number 1743 _reflns_number_total 1604 _reflns_number_observed 1546 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_theta_max 51.50 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.061 _refine_ls_wR_factor_obs 0.074 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1546 _refine_ls_number_parameters 216 _refine_ls_goodness_of_fit_obs 1.750 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.1841 _refine_ls_shift/esd_mean 0.0271 _refine_diff_density_min -0.33 _refine_diff_density_max 0.37 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.01777 _diffrn_orient_matrix_UB_12 0.03620 _diffrn_orient_matrix_UB_13 0.06347 _diffrn_orient_matrix_UB_21 -0.05083 _diffrn_orient_matrix_UB_22 0.00851 _diffrn_orient_matrix_UB_23 -0.00164 _diffrn_orient_matrix_UB_31 0.00124 _diffrn_orient_matrix_UB_32 -0.16877 _diffrn_orient_matrix_UB_33 0.01351 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z +X+0.5,+Y+0.5,+Z -X,+Y,-Z -X+0.5,+Y+0.5,-Z _symmetry_space_group_name_H-M 'C 2 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type O1 0.7524(2) -0.0293 0.1067(3) 0.046(3) 1.000 Uij O3 0.6984(3) -0.3061(12) 0.1523(3) 0.055(3) 1.000 Uij O17 0.8632(2) 0.0892(12) 0.0190(3) 0.043(3) 1.000 Uij N14 0.7914(2) 0.4080(13) 0.0770(3) 0.034(3) 1.000 Uij C2 0.7212(3) -0.1048(16) 0.1556(4) 0.038(3) 1.000 Uij C4 0.7104(3) 0.0678(15) 0.2225(4) 0.038(3) 1.000 Uij C5 0.6307(3) 0.0756(15) 0.2144(4) 0.045(4) 1.000 Uij C6 0.5829(4) 0.1431(19) 0.1232(5) 0.061(5) 1.000 Uij C7 0.6204(4) 0.2491(19) 0.2793(5) 0.063(5) 1.000 Uij C8 0.7607(3) 0.0055(15) 0.3136(4) 0.041(4) 1.000 Uij C9 0.7517(4) -0.1912(17) 0.3567(5) 0.060(5) 1.000 Uij C10 0.7972(5) -0.2394(20) 0.4411(5) 0.073(6) 1.000 Uij C11 0.8510(5) -0.0875(22) 0.4829(4) 0.070(6) 1.000 Uij C12 0.8614(5) 0.1043(21) 0.4410(5) 0.079(6) 1.000 Uij C13 0.8157(4) 0.1559(17) 0.3567(5) 0.061(5) 1.000 Uij C15 0.8706(3) 0.4580(14) 0.1006(3) 0.036(3) 1.000 Uij C16 0.9099(3) 0.2565(15) 0.0725(4) 0.040(4) 1.000 Uij C18 0.9591(4) 0.1398(16) 0.1568(4) 0.059(5) 1.000 Uij C19 0.9585(3) 0.3023(16) 0.2281(4) 0.043(4) 1.000 Uij C20 1.0008(4) 0.2942(19) 0.3159(4) 0.057(5) 1.000 Uij C21 0.9923(4) 0.4641(20) 0.3703(4) 0.060(5) 1.000 Uij C22 0.9422(4) 0.6399(19) 0.3400(4) 0.062(5) 1.000 Uij C23 0.8993(3) 0.6485(17) 0.2527(4) 0.051(4) 1.000 Uij C24 0.9089(3) 0.4773(15) 0.1975(4) 0.037(3) 1.000 Uij H4 0.72154 0.22144 0.20887 0.037 1.000 Uiso H5 0.61572 -0.07387 0.22689 0.044 1.000 Uiso H6A 0.53333 0.14954 0.11849 0.058 1.000 Uiso H6B 0.58833 0.03334 0.08219 0.058 1.000 Uiso H6C 0.59793 0.29264 0.11059 0.058 1.000 Uiso H7A 0.57078 0.25552 0.27460 0.061 1.000 Uiso H7B 0.63538 0.39952 0.26780 0.061 1.000 Uiso H7C 0.64938 0.20362 0.33720 0.061 1.000 Uiso H9 0.71341 -0.29649 0.32773 0.057 1.000 Uiso H10 0.79243 -0.38072 0.46921 0.069 1.000 Uiso H11 0.88039 -0.11177 0.54262 0.066 1.000 Uiso H12 0.90104 0.20563 0.46938 0.073 1.000 Uiso H13 0.82327 0.29361 0.32847 0.058 1.000 Uiso H14A 0.76728 0.53336 0.09364 0.032 1.000 Uiso H14B 0.78608 0.27006 0.10664 0.032 1.000 Uiso H14C 0.76978 0.38366 0.01554 0.032 1.000 Uiso H15 0.87587 0.59586 0.07104 0.033 1.000 Uiso H16 0.93869 0.31886 0.04151 0.038 1.000 Uiso H18A 1.00714 0.12478 0.15602 0.053 1.000 Uiso H18B 0.94208 -0.00659 0.16298 0.053 1.000 Uiso H20 1.03645 0.17640 0.33797 0.052 1.000 Uiso H21 1.02058 0.45961 0.43027 0.057 1.000 Uiso H22 0.936(2) 0.747(10) 0.380(3) 0.060 1.000 Uiso H17 0.85846 0.08646 -0.04111 0.041 1.000 Uiso H23 0.86404 0.76821 0.23079 0.049 1.000 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 0.050(2) 0.048(3) 0.036(2) -0.009(3) 0.024(2) -0.008(2) O3 0.087(4) 0.032(3) 0.043(3) -0.009(3) 0.034(3) -0.004(2) O17 0.051(2) 0.036(3) 0.036(2) -0.002(2) 0.016(2) -0.006(2) N14 0.036(2) 0.031(3) 0.030(2) 0.006(3) 0.009(2) -0.002(2) C2 0.039(3) 0.035(4) 0.033(3) 0.005(3) 0.008(3) -0.002(3) C4 0.047(3) 0.030(3) 0.035(3) -0.003(3) 0.019(3) -0.001(3) C5 0.049(4) 0.036(4) 0.046(3) -0.003(3) 0.024(3) -0.004(3) C6 0.050(4) 0.071(6) 0.052(4) 0.010(4) 0.015(3) -0.011(4) C7 0.060(4) 0.064(6) 0.060(4) 0.003(5) 0.029(4) -0.019(5) C8 0.047(3) 0.037(4) 0.034(3) 0.001(3) 0.019(3) -0.003(3) C9 0.072(5) 0.048(5) 0.049(4) -0.017(4) 0.017(4) 0.002(4) C10 0.098(6) 0.061(6) 0.049(4) 0.009(6) 0.026(4) 0.021(5) C11 0.083(6) 0.083(7) 0.033(4) 0.000(6) 0.014(4) 0.001(5) C12 0.085(6) 0.084(7) 0.049(4) -0.029(6) 0.004(4) -0.015(5) C13 0.075(5) 0.051(5) 0.047(4) -0.019(5) 0.019(4) -0.001(4) C15 0.040(3) 0.031(3) 0.030(3) -0.004(3) 0.009(2) 0.003(3) C16 0.042(3) 0.038(4) 0.035(3) 0.005(3) 0.013(3) 0.006(3) C18 0.070(5) 0.041(5) 0.049(4) 0.019(4) 0.003(3) 0.001(4) C19 0.046(4) 0.040(4) 0.037(3) -0.002(3) 0.007(3) 0.005(3) C20 0.058(4) 0.059(5) 0.040(4) 0.009(4) 0.002(3) 0.017(4) C21 0.063(4) 0.078(6) 0.031(3) -0.010(5) 0.009(3) 0.005(4) C22 0.056(4) 0.081(6) 0.040(4) -0.012(5) 0.017(3) -0.021(4) C23 0.041(3) 0.055(5) 0.048(4) 0.001(4) 0.012(3) -0.007(4) C24 0.034(3) 0.038(4) 0.033(3) -0.005(3) 0.009(2) 0.001(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.255(8) . . yes O3 C2 1.244(12) . . yes O17 C16 1.413(10) . . yes N14 C15 1.507(8) . . yes C2 C4 1.555(11) . . yes C4 C5 1.540(9) . . yes C4 C8 1.523(9) . . yes C5 C6 1.518(10) . . yes C5 C7 1.531(12) . . yes C8 C9 1.386(12) . . yes C8 C13 1.380(12) . . yes C9 C10 1.393(11) . . yes C10 C11 1.367(15) . . yes C11 C12 1.361(16) . . yes C12 C13 1.397(11) . . yes C15 C16 1.560(11) . . yes C15 C24 1.510(8) . . yes C16 C18 1.543(10) . . yes C18 C19 1.507(11) . . yes C19 C20 1.393(9) . . yes C19 C24 1.377(11) . . yes C20 C21 1.378(14) . . yes C21 C22 1.387(14) . . yes C22 C23 1.389(10) . . yes C23 C24 1.400(12) . . yes O17 H17 0.960(4) . . yes N14 H14A 0.960(7) . . yes N14 H14B 0.960(7) . . yes N14 H14C 0.961(5) . . yes C4 H4 0.961(9) . . yes C5 H5 0.960(9) . . yes C6 H6A 0.960(7) . . yes C6 H6B 0.960(9) . . yes C6 H6C 0.961(11) . . yes C7 H7A 0.960(8) . . yes C7 H7B 0.960(11) . . yes C7 H7C 0.961(8) . . yes C9 H9 0.960(9) . . yes C10 H10 0.960(11) . . yes C11 H11 0.960(8) . . yes C12 H12 0.960(11) . . yes C13 H13 0.960(9) . . yes C15 H15 0.960(8) . . yes C16 H16 0.960(7) . . yes C18 H18A 0.961(8) . . yes C18 H18B 0.931(10) . . yes C20 H20 0.957(10) . . yes C21 H21 0.949(7) . . yes C22 H22 0.94(6) . . yes C23 H23 0.960(9) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 O3 123.5(7) . . . yes O1 C2 C4 116.9(7) . . . yes O3 C2 C4 119.6(6) . . . yes C2 C4 C5 110.5(6) . . . yes C2 C4 C8 109.8(6) . . . yes C5 C4 C8 112.9(5) . . . yes C4 C5 C6 111.0(6) . . . yes C4 C5 C7 110.1(6) . . . yes C6 C5 C7 109.3(7) . . . yes C4 C8 C9 122.7(7) . . . yes C4 C8 C13 118.8(7) . . . yes C9 C8 C13 118.4(7) . . . yes C8 C9 C10 121.3(9) . . . yes C9 C10 C11 119.4(10) . . . yes C10 C11 C12 120.0(8) . . . yes C11 C12 C13 121.1(9) . . . yes C8 C13 C12 119.7(9) . . . yes N14 C15 C16 111.4(6) . . . yes N14 C15 C24 112.3(5) . . . yes C16 C15 C24 104.5(6) . . . yes O17 C16 C15 114.2(5) . . . yes O17 C16 C18 109.3(7) . . . yes C15 C16 C18 106.5(6) . . . yes C16 C18 C19 104.5(7) . . . yes C18 C19 C20 128.2(8) . . . yes C18 C19 C24 112.0(6) . . . yes C20 C19 C24 119.7(8) . . . yes C19 C20 C21 118.9(9) . . . yes C20 C21 C22 121.7(7) . . . yes C21 C22 C23 119.9(9) . . . yes C22 C23 C24 118.1(8) . . . yes C15 C24 C19 111.2(7) . . . yes C15 C24 C23 127.1(7) . . . yes C19 C24 C23 121.7(6) . . . yes C16 O17 H17 117.3(6) . . . yes C15 N14 H14A 111.1(6) . . . yes C15 N14 H14B 108.6(5) . . . yes C15 N14 H14C 109.8(5) . . . yes H14A N14 H14B 109.3(5) . . . yes H14A N14 H14C 109.2(6) . . . yes H14B N14 H14C 109.0(7) . . . yes C2 C4 H4 109.3(6) . . . yes C5 C4 H4 105.4(7) . . . yes C8 C4 H4 108.9(6) . . . yes C4 C5 H5 109.9(7) . . . yes C6 C5 H5 108.1(7) . . . yes C7 C5 H5 108.3(7) . . . yes C5 C6 H6A 110.8(7) . . . yes C5 C6 H6B 109.8(9) . . . yes C5 C6 H6C 108.2(7) . . . yes H6A C6 H6B 109.5(9) . . . yes H6A C6 H6C 109.5(10) . . . yes H6B C6 H6C 109.0(7) . . . yes C5 C7 H7A 110.7(8) . . . yes C5 C7 H7B 109.3(7) . . . yes C5 C7 H7C 109.4(9) . . . yes H7A C7 H7B 109.2(10) . . . yes H7A C7 H7C 109.3(8) . . . yes H7B C7 H7C 109.0(9) . . . yes C8 C9 H9 119.3(7) . . . yes C10 C9 H9 119.4(10) . . . yes C9 C10 H10 120.8(10) . . . yes C11 C10 H10 119.8(8) . . . yes C10 C11 H11 120.4(11) . . . yes C12 C11 H11 119.5(11) . . . yes C11 C12 H12 119.7(9) . . . yes C13 C12 H12 119.2(11) . . . yes C8 C13 H13 120.3(7) . . . yes C12 C13 H13 120.0(9) . . . yes N14 C15 H15 108.6(6) . . . yes C16 C15 H15 108.4(6) . . . yes C24 C15 H15 111.7(7) . . . yes O17 C16 H16 108.0(6) . . . yes C15 C16 H16 109.2(8) . . . yes C18 C16 H16 109.6(6) . . . yes C16 C18 H18A 110.2(7) . . . yes C16 C18 H18B 110.9(7) . . . yes C19 C18 H18A 110.3(7) . . . yes C19 C18 H18B 112.3(7) . . . yes H18A C18 H18B 108.6(9) . . . yes C19 C20 H20 120.9(9) . . . yes C21 C20 H20 120.2(7) . . . yes C20 C21 H21 119.6(10) . . . yes C22 C21 H21 118.7(10) . . . yes C21 C22 H22 119.3(30) . . . yes C23 C22 H22 120.7(30) . . . yes C22 C23 H23 120.9(9) . . . yes C24 C23 H23 120.9(7) . . . yes #===END data_AImtpa _publ_section_title ; Crystal and molecular structure of (1S,2R)-1-Amino-2-indanol/(S)-a,a,a-Methoxytrifluoromethylphenylacetic acid ; _publ_section_abstract ; We present the crystal and molecular structure of (1S,2R)-2/(S)-7 ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo' ; Dept. of Chemistry and Biotechnology, Graduate School of Engineering The University of Tokyo 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-8656 Japan ; _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _chemical_formula_moiety 'C19 H20 N1 O4 F3 ' _chemical_formula_weight 380.00 _cell_length_a 15.787(2) _cell_length_b 6.3359(8) _cell_length_c 9.353(1) _cell_angle_alpha 90.000000(0) _cell_angle_beta 99.428(8) _cell_angle_gamma 90.000000(0) _cell_volume 922.9(2) _cell_measurement_reflns_used '20' _cell_measurement_theta_min '1.5' _cell_measurement_theta_max '30' _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_meas 1.367 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 0.998 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1792 _reflns_number_total 1613 _reflns_number_observed 1487 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_theta_max 51.32 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.047 _refine_ls_wR_factor_obs 0.056 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1487 _refine_ls_number_parameters 246 _refine_ls_goodness_of_fit_obs 1.017 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0295 _refine_ls_shift/esd_mean 0.0051 _refine_diff_density_min -0.22 _refine_diff_density_max 0.21 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.03254 _diffrn_orient_matrix_UB_12 -0.00643 _diffrn_orient_matrix_UB_13 -0.08307 _diffrn_orient_matrix_UB_21 0.04987 _diffrn_orient_matrix_UB_22 0.07188 _diffrn_orient_matrix_UB_23 0.06032 _diffrn_orient_matrix_UB_31 0.02403 _diffrn_orient_matrix_UB_32 -0.14036 _diffrn_orient_matrix_UB_33 0.03474 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,+Y+0.5,-Z _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' #================================================== # 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_occupancy _atom_site_thermal_displace_type F9 0.58627(10) 0.15700 0.34210(18) 0.073(1) 1.000 Uij F8 0.63744(10) 0.28793(42) 0.54898(16) 0.074(1) 1.000 Uij F10 0.54236(10) 0.45822(46) 0.40460(21) 0.089(1) 1.000 Uij O3 0.83299(10) 0.43311(40) 0.35197(18) 0.054(1) 1.000 Uij O5 0.69173(11) 0.66163(42) 0.39246(18) 0.056(1) 1.000 Uij O20 0.97627(10) 0.20709(40) 0.41475(17) 0.0482(9) 1.000 Uij O1 0.76642(12) 0.14140(40) 0.39675(23) 0.066(1) 1.000 Uij N17 0.88726(11) -0.15314(42) 0.37508(19) 0.039(1) 1.000 Uij C2 0.76729(14) 0.33125(50) 0.36780(24) 0.042(1) 1.000 Uij C4 0.68107(14) 0.45152(49) 0.33989(24) 0.045(1) 1.000 Uij C6 0.7173(2) 0.6912(6) 0.5440(3) 0.072(2) 1.000 Uij C7 0.61222(15) 0.33683(57) 0.40937(28) 0.057(2) 1.000 Uij C11 0.64968(13) 0.46925(51) 0.17758(24) 0.045(1) 1.000 Uij C12 0.60632(16) 0.65242(57) 0.12181(29) 0.061(2) 1.000 Uij C13 0.57580(18) 0.66793(69) -0.02546(32) 0.071(2) 1.000 Uij C14 0.58731(17) 0.50467(74) -0.11734(29) 0.073(2) 1.000 Uij C15 0.62991(17) 0.32704(72) -0.06374(28) 0.072(2) 1.000 Uij C16 0.66103(16) 0.30770(57) 0.08312(28) 0.060(2) 1.000 Uij C18 0.94016(13) -0.10936(48) 0.26096(23) 0.041(1) 1.000 Uij C19 0.99690(14) 0.09194(51) 0.29478(25) 0.047(1) 1.000 Uij C21 0.98599(19) 0.21875(58) 0.15593(30) 0.070(2) 1.000 Uij C22 0.91325(15) 0.11770(52) 0.05626(25) 0.051(1) 1.000 Uij C23 0.8731(2) 0.1807(6) -0.0801(3) 0.069(2) 1.000 Uij C24 0.8091(2) 0.0579(7) -0.1543(3) 0.076(2) 1.000 Uij C25 0.78278(17) -0.12380(75) -0.09567(29) 0.074(2) 1.000 Uij C26 0.82183(15) -0.18732(59) 0.04128(26) 0.059(2) 1.000 Uij C27 0.88672(14) -0.06753(53) 0.11508(24) 0.045(1) 1.000 Uij H6A 0.7255(15) 0.8336(49) 0.5786(28) 0.072 1.000 Uiso H6B 0.77050 0.61731 0.57241 0.072 1.000 Uiso H6C 0.67410 0.62821 0.59151 0.072 1.000 Uiso H12 0.59842 0.76592 0.18631 0.060 1.000 Uiso H13 0.54540 0.79232 -0.06336 0.071 1.000 Uiso H14 0.56561 0.51577 -0.21914 0.072 1.000 Uiso H15 0.63941 0.21514 -0.12854 0.071 1.000 Uiso H16 0.68903 0.17990 0.12022 0.059 1.000 Uiso H17A 0.85276 -0.27744 0.35308 0.038 1.000 Uiso H17B 0.85036 -0.03504 0.38358 0.038 1.000 Uiso H17C 0.92476 -0.17324 0.46568 0.038 1.000 Uiso H18 0.97606 -0.22906 0.25136 0.041 1.000 Uiso H19 1.05590 0.04874 0.31688 0.047 1.000 Uiso H20 0.9328(15) 0.2571(49) 0.4002(28) 0.047 1.000 Uiso H21A 1.03759 0.21675 0.11403 0.069 1.000 Uiso H21B 0.97209 0.36235 0.17533 0.069 1.000 Uiso H23 0.88874 0.31099 -0.12117 0.069 1.000 Uiso H24 0.78494 0.09630 -0.25169 0.075 1.000 Uiso H25 0.73638 -0.20250 -0.15007 0.073 1.000 Uiso H26 0.80253 -0.31252 0.08398 0.058 1.000 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 F9 0.0662(9) 0.0706(12) 0.0812(10) -.0280(10) 0.0116(8) -.0074(10) F8 0.085(1) 0.078(1) 0.057(1) -0.011(1) 0.018(1) 0.009(1) F10 0.0605(9) 0.1017(16) 0.1067(13) 0.0173(12) 0.0341(9) 0.0132(13) O3 0.0430(8) 0.0383(10) 0.0779(11) -.0024(9) 0.0052(8) 0.0027(9) O5 0.073(1) 0.037(1) 0.056(1) 0.009(1) 0.007(1) -0.008(1) O20 0.0448(8) 0.0437(10) 0.0525(9) 0.0011(8) -.0057(7) -.0114(8) O1 0.055(1) 0.039(1) 0.103(1) 0.005(1) 0.017(1) 0.015(1) N17 0.0401(9) 0.0328(10) 0.0420(9) -.0007(9) -.0015(7) 0.0016(8) C2 0.042(1) 0.036(1) 0.046(1) 0.000(1) 0.001(1) 0.003(1) C4 0.050(1) 0.034(1) 0.049(1) -0.001(1) 0.006(1) -0.004(1) C6 0.098(2) 0.061(2) 0.055(1) -0.014(2) 0.015(1) -0.016(2) C7 0.048(1) 0.061(2) 0.061(2) -0.001(1) 0.009(1) 0.001(1) C11 0.037(1) 0.048(2) 0.050(1) 0.002(1) 0.006(1) 0.002(1) C12 0.055(1) 0.063(2) 0.062(1) 0.014(1) 0.005(1) 0.005(1) C13 0.059(1) 0.085(2) 0.068(2) 0.018(2) 0.003(1) 0.024(2) C14 0.050(1) 0.117(3) 0.049(1) 0.009(2) 0.003(1) 0.007(2) C15 0.059(1) 0.101(3) 0.052(1) 0.015(2) 0.002(1) -0.019(2) C16 0.054(1) 0.064(2) 0.058(1) 0.015(1) -0.001(1) -0.009(1) C18 0.043(1) 0.033(1) 0.046(1) -0.002(1) 0.005(1) -0.002(1) C19 0.039(1) 0.047(1) 0.055(1) -0.008(1) 0.008(1) -0.010(1) C21 0.087(2) 0.057(2) 0.063(2) -0.024(2) 0.019(1) -0.004(1) C22 0.057(1) 0.049(2) 0.048(1) 0.000(1) 0.016(1) 0.000(1) C23 0.087(2) 0.067(2) 0.052(1) 0.017(2) 0.024(1) 0.014(2) C24 0.070(2) 0.109(3) 0.045(1) 0.017(2) 0.001(1) 0.004(2) C25 0.059(2) 0.107(3) 0.052(1) -0.015(2) -0.001(1) -0.012(2) C26 0.053(1) 0.069(2) 0.052(1) -0.018(1) 0.007(1) -0.003(1) C27 0.042(1) 0.047(1) 0.045(1) -0.004(1) 0.008(1) -0.001(1) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F9 C7 1.333(4) . . yes F8 C7 1.338(4) . . yes F10 C7 1.339(4) . . yes O3 C2 1.251(4) . . yes O5 C4 1.420(4) . . yes O5 C6 1.421(4) . . yes O20 C19 1.420(4) . . yes O1 C2 1.234(5) . . yes N17 C18 1.485(3) . . yes C2 C4 1.544(4) . . yes C4 C7 1.537(4) . . yes C4 C11 1.522(4) . . yes C11 C12 1.404(5) . . yes C11 C16 1.383(5) . . yes C12 C13 1.386(4) . . yes C13 C14 1.376(6) . . yes C14 C15 1.364(6) . . yes C15 C16 1.386(4) . . yes C18 C19 1.561(5) . . yes C18 C27 1.505(4) . . yes C19 C21 1.513(5) . . yes C21 C22 1.499(4) . . yes C22 C23 1.386(4) . . yes C22 C27 1.390(5) . . yes C23 C24 1.370(5) . . yes C24 C25 1.369(6) . . yes C25 C26 1.387(4) . . yes C26 C27 1.368(4) . . yes O20 H20 0.75(3) . . yes N17 H17A 0.960(3) . . yes N17 H17B 0.960(3) . . yes N17 H17C 0.959(2) . . yes C6 H6A 0.96(4) . . yes C6 H6B 0.960(4) . . yes C6 H6C 0.960(4) . . yes C12 H12 0.960(4) . . yes C13 H13 0.960(4) . . yes C14 H14 0.960(3) . . yes C15 H15 0.960(4) . . yes C16 H16 0.960(4) . . yes C18 H18 0.960(3) . . yes C19 H19 0.960(3) . . yes C21 H21A 0.960(3) . . yes C21 H21B 0.960(4) . . yes C23 H23 0.960(4) . . yes C24 H24 0.960(3) . . yes C25 H25 0.960(4) . . yes C26 H26 0.960(4) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O5 C6 117.9(3) . . . yes O3 C2 O1 124.6(3) . . . yes O3 C2 C4 116.8(3) . . . yes O1 C2 C4 118.5(3) . . . yes O5 C4 C2 110.7(2) . . . yes O5 C4 C7 110.4(3) . . . yes O5 C4 C11 106.1(3) . . . yes C2 C4 C7 111.1(3) . . . yes C2 C4 C11 109.8(2) . . . yes C7 C4 C11 108.6(2) . . . yes F9 C7 F8 106.4(3) . . . yes F9 C7 F10 106.7(3) . . . yes F9 C7 C4 112.9(3) . . . yes F8 C7 F10 106.1(3) . . . yes F8 C7 C4 113.8(3) . . . yes F10 C7 C4 110.5(3) . . . yes C4 C11 C12 119.4(3) . . . yes C4 C11 C16 121.8(3) . . . yes C12 C11 C16 118.7(3) . . . yes C11 C12 C13 119.8(4) . . . yes C12 C13 C14 120.5(4) . . . yes C13 C14 C15 119.9(3) . . . yes C14 C15 C16 120.7(4) . . . yes C11 C16 C15 120.4(4) . . . yes N17 C18 C19 112.2(2) . . . yes N17 C18 C27 112.7(2) . . . yes C19 C18 C27 104.9(3) . . . yes O20 C19 C18 112.4(2) . . . yes O20 C19 C21 113.4(3) . . . yes C18 C19 C21 106.2(3) . . . yes C19 C21 C22 106.0(3) . . . yes C21 C22 C23 129.6(3) . . . yes C21 C22 C27 111.4(3) . . . yes C23 C22 C27 119.0(3) . . . yes C22 C23 C24 119.4(4) . . . yes C23 C24 C25 121.5(3) . . . yes C24 C25 C26 119.7(4) . . . yes C25 C26 C27 119.2(4) . . . yes C18 C27 C22 110.3(3) . . . yes C18 C27 C26 128.5(3) . . . yes C22 C27 C26 121.2(3) . . . yes C19 O20 H20 113.3(21) . . . yes C18 N17 H17A 111.4(2) . . . yes C18 N17 H17B 109.5(3) . . . yes C18 N17 H17C 108.7(2) . . . yes H17A N17 H17B 109.1(2) . . . yes H17A N17 H17C 109.1(3) . . . yes H17B N17 H17C 109.0(3) . . . yes O5 C6 H6A 117.4(17) . . . yes O5 C6 H6B 107.7(3) . . . yes O5 C6 H6C 107.4(3) . . . yes H6A C6 H6B 107.5(15) . . . yes H6A C6 H6C 107.6(15) . . . yes H6B C6 H6C 109.0(4) . . . yes C11 C12 H12 119.4(3) . . . yes C13 C12 H12 120.8(4) . . . yes C12 C13 H13 119.8(4) . . . yes C14 C13 H13 119.7(3) . . . yes C13 C14 H14 120.1(5) . . . yes C15 C14 H14 120.0(4) . . . yes C14 C15 H15 119.7(3) . . . yes C16 C15 H15 119.6(4) . . . yes C11 C16 H16 119.6(3) . . . yes C15 C16 H16 120.0(4) . . . yes N17 C18 H18 109.3(3) . . . yes C19 C18 H18 109.7(2) . . . yes C27 C18 H18 107.8(3) . . . yes O20 C19 H19 108.4(3) . . . yes C18 C19 H19 108.4(3) . . . yes C21 C19 H19 107.8(3) . . . yes C19 C21 H21A 111.0(3) . . . yes C19 C21 H21B 109.8(3) . . . yes C22 C21 H21A 110.8(3) . . . yes C22 C21 H21B 110.3(3) . . . yes H21A C21 H21B 109.0(4) . . . yes C22 C23 H23 120.5(4) . . . yes C24 C23 H23 120.1(3) . . . yes C23 C24 H24 118.9(4) . . . yes C25 C24 H24 119.6(4) . . . yes C24 C25 H25 118.7(3) . . . yes C26 C25 H25 121.6(4) . . . yes C25 C26 H26 120.0(3) . . . yes C27 C26 H26 120.7(3) . . . yes #===END