# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/250 data_global # SUBMISSION DETAILS _publ_contact_author_name 'Kazuhiko Saigo' _publ_contact_author_address ; Department of Integrated biosciences, Graduate School of Frontier Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656, Japan ; _publ_contact_author_email saigo@chiral.t.u-tokyo.ac.jp _publ_contact_author_fax +81-3-5802-3348 _publ_contact_author_phone +81-3-5841-7266 _publ_requested_journal Perkin #============================================================================== data_rngarh _chemical_name_systematic ; (R)-1-Phenylethylammonium (R)-2-Naphthylglycolate ; _chemical_name_common (R)-2/(R)-3a _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _chemical_formula_moiety 'C20 H21 N1 O3 ' _chemical_formula_weight 323.40 _chemical_melting_point 184-187.5 _cell_length_a 30.573(7) _cell_length_b 6.835(2) _cell_length_c 8.446(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 100.26(2) _cell_angle_gamma 90.000000(0) _cell_volume 1736.6(9) _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 1.236 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 6.67 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'numerical' _diffrn_reflns_number 1648 _reflns_number_total 1485 _reflns_number_observed 1367 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_theta_max 51.32 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.061 _refine_ls_wR_factor_obs 0.076 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1367 _refine_ls_number_parameters 218 _refine_ls_goodness_of_fit_obs 1.347 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0315 _refine_ls_shift/esd_mean 0.0088 _refine_diff_density_min -0.21 _refine_diff_density_max 0.33 _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 -0.01044 _diffrn_orient_matrix_UB_12 -0.01258 _diffrn_orient_matrix_UB_13 -0.11868 _diffrn_orient_matrix_UB_21 -0.03084 _diffrn_orient_matrix_UB_22 0.03506 _diffrn_orient_matrix_UB_23 0.01401 _diffrn_orient_matrix_UB_31 0.00670 _diffrn_orient_matrix_UB_32 0.14149 _diffrn_orient_matrix_UB_33 -0.01406 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 -0.25145(9) -0.26730 -0.28602(31) 0.053(1) 1.000 Uij O3 -0.23972(9) -0.55000(55) -0.15635(30) 0.053(1) 1.000 Uij O5 -0.20166(13) -0.70793(56) -0.38289(40) 0.067(2) 1.000 Uij N16 -0.21231(9) 0.05285(53) -0.08759(33) 0.047(2) 1.000 Uij C2 -0.23577(11) -0.43767(61) -0.26905(39) 0.041(2) 1.000 Uij C4 -0.21134(12) -0.50771(65) -0.40080(42) 0.046(2) 1.000 Uij C6 -0.16979(13) -0.38701(66) -0.39993(40) 0.051(2) 1.000 Uij C7 -0.13033(14) -0.42913(84) -0.30956(51) 0.069(3) 1.000 Uij C8 -0.09163(16) -0.30058(92) -0.30931(49) 0.072(3) 1.000 Uij C9 -0.05121(18) -0.34386(137) -0.21647(75) 0.104(4) 1.000 Uij C10 -0.0174(2) -0.2187(17) -0.2209(9) 0.118(5) 1.000 Uij C11 -0.0206(2) -0.0494(15) -0.3111(8) 0.112(5) 1.000 Uij C12 -0.0605(2) -0.0033(13) -0.4036(8) 0.106(5) 1.000 Uij C13 -0.09929(14) -0.13640(78) -0.40510(50) 0.064(3) 1.000 Uij C14 -0.14056(16) -0.09405(86) -0.49992(60) 0.076(3) 1.000 Uij C15 -0.17504(15) -0.21360(80) -0.49734(57) 0.066(3) 1.000 Uij C17 -0.16425(13) 0.00124(65) -0.05320(43) 0.054(2) 1.000 Uij C18 -0.15824(16) -0.19389(75) 0.03463(57) 0.067(3) 1.000 Uij C19 -0.13620(12) 0.15819(67) 0.04178(40) 0.049(2) 1.000 Uij C20 -0.09229(14) 0.17220(88) 0.02300(55) 0.071(3) 1.000 Uij C21 -0.06335(16) 0.30162(101) 0.12000(73) 0.085(4) 1.000 Uij C22 -0.07881(16) 0.41567(94) 0.23416(61) 0.079(3) 1.000 Uij C23 -0.12264(16) 0.39965(77) 0.25084(51) 0.067(3) 1.000 Uij C24 -0.15086(13) 0.27426(68) 0.15373(47) 0.053(2) 1.000 Uij H4 -0.2316(18) -0.4816(95) -0.5173(63) 0.05(1) 1.000 Uiso H5 -0.2073(18) -0.7462(95) -0.4478(63) 0.067(6) 1.000 Uiso H7 -0.1266(7) -0.5606(35) -0.2375(29) 0.068(6) 1.000 Uiso H9 -0.0467(7) -0.4730(40) -0.1417(32) 0.102(7) 1.000 Uiso H10 0.0147(9) -0.2515(44) -0.1499(33) 0.118(8) 1.000 Uiso H11 0.0077(10) 0.0452(52) -0.3102(43) 0.11(1) 1.000 Uiso H12 -0.0642(10) 0.1286(56) -0.4750(36) 0.11(1) 1.000 Uiso H14 -0.1445(14) 0.0347(73) -0.5753(50) 0.08(1) 1.000 Uiso H15 -0.2072(11) -0.1791(46) -0.5675(34) 0.066(9) 1.000 Uiso H16A -0.2302(9) -0.0463(47) -0.1482(39) 0.046(9) 1.000 Uiso H16B -0.2225(10) 0.0719(48) 0.0124(34) 0.046(8) 1.000 Uiso H16C -0.2159(10) 0.1727(54) -0.1477(37) 0.05(1) 1.000 Uiso H17 -0.1530(9) -0.0202(51) -0.1659(33) 0.053(8) 1.000 Uiso H18A -0.1234(11) -0.2312(57) 0.0594(40) 0.07(1) 1.000 Uiso H18B -0.1708(9) -0.1844(47) 0.1460(35) 0.065(9) 1.000 Uiso H18C -0.1766(8) -0.3052(51) -0.0402(31) 0.065(8) 1.000 Uiso H20 -0.080(3) 0.083(14) -0.066(10) 0.07(4) 1.000 Uiso H21 -0.0290(12) 0.3105(52) 0.1056(39) 0.08(1) 1.000 Uiso H22 -0.05701 0.51667 0.30836 0.076 1.000 Uiso H23 -0.13494 0.48695 0.34024 0.066 1.000 Uiso H24 -0.18516 0.26616 0.16773 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 0.063(2) 0.044(2) 0.052(1) 0.010(1) 0.015(1) 0.006(1) O3 0.073(2) 0.041(1) 0.046(1) 0.005(1) 0.019(1) 0.008(1) O5 0.085(2) 0.046(2) 0.071(2) -0.003(2) 0.022(2) -0.014(2) N16 0.056(2) 0.040(2) 0.043(1) 0.002(1) 0.008(1) 0.005(1) C2 0.046(2) 0.037(2) 0.036(2) 0.001(2) 0.002(1) -0.001(2) C4 0.054(2) 0.041(2) 0.042(2) 0.003(2) 0.008(2) -0.004(2) C6 0.059(2) 0.051(2) 0.042(2) 0.003(2) 0.016(2) -0.004(2) C7 0.066(2) 0.080(3) 0.058(2) 0.000(2) 0.012(2) 0.007(2) C8 0.078(3) 0.082(3) 0.055(2) 0.009(3) 0.015(2) -0.002(3) C9 0.068(3) 0.137(6) 0.101(4) -0.002(4) 0.002(3) 0.011(4) C10 0.068(3) 0.175(8) 0.111(5) -0.024(5) 0.023(3) -0.004(6) C11 0.076(4) 0.165(8) 0.095(4) -0.054(4) 0.026(3) -0.028(5) C12 0.096(4) 0.125(5) 0.097(4) -0.033(4) 0.040(3) -0.015(4) C13 0.064(2) 0.069(3) 0.057(2) -0.004(2) 0.019(2) -0.008(2) C14 0.083(3) 0.065(3) 0.081(3) 0.011(3) 0.030(3) 0.023(3) C15 0.071(3) 0.059(3) 0.067(3) 0.004(2) 0.024(2) 0.010(2) C17 0.063(2) 0.048(2) 0.050(2) 0.017(2) 0.016(2) 0.005(2) C18 0.079(3) 0.048(2) 0.070(3) 0.011(2) -0.004(2) 0.003(2) C19 0.053(2) 0.053(2) 0.040(2) 0.007(2) 0.009(2) 0.011(2) C20 0.059(2) 0.081(3) 0.072(3) 0.012(2) 0.018(2) 0.007(3) C21 0.062(3) 0.086(4) 0.102(4) -0.001(3) 0.009(3) 0.020(4) C22 0.075(3) 0.075(3) 0.079(3) -0.015(3) -0.010(2) 0.014(3) C23 0.088(3) 0.050(3) 0.061(2) 0.000(2) 0.010(2) 0.001(2) C24 0.060(2) 0.046(2) 0.051(2) 0.003(2) 0.014(2) 0.004(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 1.258(5) . . yes O3 C2 1.245(5) . . yes O5 C4 1.403(6) . . yes N16 C17 1.489(5) . . yes C2 C4 1.524(5) . . yes C4 C6 1.514(6) . . yes C6 C7 1.339(6) . . yes C6 C15 1.435(7) . . yes C7 C8 1.473(8) . . yes C8 C9 1.373(8) . . yes C8 C13 1.379(8) . . yes C9 C10 1.347(12) . . yes C10 C11 1.379(14) . . yes C11 C12 1.361(9) . . yes C12 C13 1.493(9) . . yes C13 C14 1.399(7) . . yes C14 C15 1.337(8) . . yes C17 C18 1.521(7) . . yes C17 C19 1.511(6) . . yes C19 C20 1.383(6) . . yes C19 C24 1.369(6) . . yes C20 C21 1.406(8) . . yes C21 C22 1.387(9) . . yes C22 C23 1.376(7) . . yes C23 C24 1.378(7) . . yes O5 H5 0.60(6) . . yes N16 H16A 0.96(4) . . yes N16 H16B 0.96(3) . . yes N16 H16C 0.96(4) . . yes C4 H4 1.08(6) . . yes C7 H7 1.08(3) . . yes C9 H9 1.08(3) . . yes C10 H10 1.08(3) . . yes C11 H11 1.08(4) . . yes C12 H12 1.08(4) . . yes C14 H14 1.08(5) . . yes C15 H15 1.08(4) . . yes C17 H17 1.08(3) . . yes C18 H18A 1.08(4) . . yes C18 H18B 1.08(3) . . yes C18 H18C 1.08(4) . . yes C20 H20 1.08(10) . . yes C21 H21 1.08(4) . . yes C22 H22 1.079(6) . . yes C23 H23 1.081(5) . . yes C24 H24 1.077(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 124.8(4) . . . yes O1 C2 C4 115.7(4) . . . yes O3 C2 C4 119.4(4) . . . yes O5 C4 C2 110.4(4) . . . yes O5 C4 C6 111.7(4) . . . yes C2 C4 C6 110.2(4) . . . yes C4 C6 C7 123.8(4) . . . yes C4 C6 C15 116.1(4) . . . yes C7 C6 C15 120.1(5) . . . yes C6 C7 C8 121.0(5) . . . yes C7 C8 C9 120.9(6) . . . yes C7 C8 C13 115.6(5) . . . yes C9 C8 C13 123.5(6) . . . yes C8 C9 C10 117.6(8) . . . yes C9 C10 C11 124.7(7) . . . yes C10 C11 C12 118.7(8) . . . yes C11 C12 C13 119.5(7) . . . yes C8 C13 C12 116.0(5) . . . yes C8 C13 C14 123.1(5) . . . yes C12 C13 C14 120.9(5) . . . yes C13 C14 C15 119.8(6) . . . yes C6 C15 C14 120.4(5) . . . yes N16 C17 C18 109.4(4) . . . yes N16 C17 C19 112.5(4) . . . yes C18 C17 C19 110.8(4) . . . yes C17 C19 C20 117.3(4) . . . yes C17 C19 C24 123.6(4) . . . yes C20 C19 C24 118.9(4) . . . yes C19 C20 C21 120.0(5) . . . yes C20 C21 C22 120.1(5) . . . yes C21 C22 C23 119.0(5) . . . yes C22 C23 C24 120.4(5) . . . yes C19 C24 C23 121.6(4) . . . yes C4 O5 H5 107.7(60) . . . yes C17 N16 H16A 112.7(18) . . . yes C17 N16 H16B 108.9(18) . . . yes C17 N16 H16C 108.8(19) . . . yes H16A N16 H16B 108.7(26) . . . yes H16A N16 H16C 108.7(28) . . . yes H16B N16 H16C 109.0(28) . . . yes O5 C4 H4 109.6(35) . . . yes C2 C4 H4 109.7(30) . . . yes C6 C4 H4 105.1(32) . . . yes C6 C7 H7 119.6(12) . . . yes C8 C7 H7 119.5(12) . . . yes C8 C9 H9 121.2(14) . . . yes C10 C9 H9 121.1(14) . . . yes C9 C10 H10 118.6(18) . . . yes C11 C10 H10 116.7(18) . . . yes C10 C11 H11 121.3(20) . . . yes C12 C11 H11 120.0(20) . . . yes C11 C12 H12 120.5(18) . . . yes C13 C12 H12 120.0(18) . . . yes C13 C14 H14 120.0(23) . . . yes C15 C14 H14 120.2(23) . . . yes C6 C15 H15 119.5(18) . . . yes C14 C15 H15 120.1(18) . . . yes N16 C17 H17 108.7(15) . . . yes C18 C17 H17 106.4(19) . . . yes C19 C17 H17 108.9(17) . . . yes C17 C18 H18A 109.4(21) . . . yes C17 C18 H18B 109.9(18) . . . yes C17 C18 H18C 109.1(17) . . . yes H18A C18 H18B 109.7(24) . . . yes H18A C18 H18C 109.9(25) . . . yes H18B C18 H18C 108.8(22) . . . yes C19 C20 H20 120.2(48) . . . yes C21 C20 H20 119.9(48) . . . yes C20 C21 H21 119.5(19) . . . yes C22 C21 H21 120.3(19) . . . yes C21 C22 H22 120.8(5) . . . yes C23 C22 H22 120.2(5) . . . yes C22 C23 H23 119.6(5) . . . yes C24 C23 H23 120.0(5) . . . yes C19 C24 H24 119.4(4) . . . yes C23 C24 H24 119.0(4) . . . yes #===END data_smomsnma _chemical_name_systematic ; (S)-1-m-Methoxyphenylethylammonium (S)-2-Naphthylglycolate ; _chemical_name_common (S)-2/(S)-3e _chemical_compound_source 'Saigol laboratory' _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.15 _chemical_formula_moiety 'C21 H23 O4 N1 ' _chemical_formula_weight 353.40 _chemical_melting_point 168.0-170.0 _cell_length_a 8.342(1) _cell_length_b 32.625(5) _cell_length_c 6.893(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 90.000000(0) _cell_angle_gamma 90.000000(0) _cell_volume 1875.9(6) _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 1.251 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 7.02 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1916 _reflns_number_total 1603 _reflns_number_observed 1312 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.086 _diffrn_reflns_theta_max 51.41 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.053 _refine_ls_wR_factor_obs 0.057 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1312 _refine_ls_number_parameters 238 _refine_ls_goodness_of_fit_obs 1.159 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.2977 _refine_ls_shift/esd_mean 0.0377 _refine_diff_density_min -0.26 _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 -0.11458 _diffrn_orient_matrix_UB_12 -0.00892 _diffrn_orient_matrix_UB_13 0.00629 _diffrn_orient_matrix_UB_21 0.03510 _diffrn_orient_matrix_UB_22 -0.02843 _diffrn_orient_matrix_UB_23 0.03379 _diffrn_orient_matrix_UB_31 -0.00325 _diffrn_orient_matrix_UB_32 0.00720 _diffrn_orient_matrix_UB_33 0.14094 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X+0.5,-Y,+Z+0.5 +X+0.5,-Y+0.5,-Z -X,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' #================================================== # 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 0.4665(5) -0.0013(1) 0.4477(6) 0.043(2) 1.000 Uij O3 0.5877(5) 0.0089(1) 0.1644(6) 0.045(3) 1.000 Uij O5 0.3340(6) 0.0444(2) 0.0076(9) 0.055(3) 1.000 Uij O25 0.7390(7) 0.2149(1) 0.0139(9) 0.079(4) 1.000 Uij N16 0.6345(6) 0.0354(1) -0.2335(7) 0.038(3) 1.000 Uij C2 0.4725(7) 0.0124(2) 0.2769(10) 0.037(3) 1.000 Uij C4 0.3219(7) 0.0355(2) 0.2085(9) 0.040(4) 1.000 Uij C6 0.2985(7) 0.0741(2) 0.3285(9) 0.041(4) 1.000 Uij C7 0.3654(8) 0.1102(2) 0.2763(10) 0.049(4) 1.000 Uij C8 0.3404(8) 0.1464(2) 0.3924(11) 0.054(4) 1.000 Uij C9 0.4105(11) 0.1836(2) 0.3428(14) 0.080(6) 1.000 Uij C10 0.3779(12) 0.2176(3) 0.4527(17) 0.095(7) 1.000 Uij C11 0.2772(12) 0.2157(3) 0.6145(17) 0.093(7) 1.000 Uij C12 0.2094(10) 0.1798(3) 0.6707(13) 0.080(6) 1.000 Uij C13 0.2412(8) 0.1429(2) 0.5581(10) 0.053(4) 1.000 Uij C14 0.1732(9) 0.1054(2) 0.6075(10) 0.060(5) 1.000 Uij C15 0.2018(8) 0.0715(2) 0.4979(10) 0.051(4) 1.000 Uij C17 0.6392(7) 0.0804(2) -0.2865(9) 0.041(4) 1.000 Uij C18 0.7239(8) 0.0849(2) -0.4808(9) 0.048(4) 1.000 Uij C19 0.7212(7) 0.1056(2) -0.1303(9) 0.039(4) 1.000 Uij C20 0.8402(8) 0.0904(2) -0.0106(10) 0.043(4) 1.000 Uij C21 0.9218(8) 0.1167(2) 0.1130(10) 0.050(4) 1.000 Uij C22 0.8865(8) 0.1577(2) 0.1209(10) 0.053(4) 1.000 Uij C23 0.7669(9) 0.1731(2) 0.0007(11) 0.054(4) 1.000 Uij C24 0.6835(8) 0.1477(2) -0.1269(9) 0.046(4) 1.000 Uij C26 0.6179(12) 0.2328(2) -0.1048(14) 0.093(7) 1.000 Uij H4 0.219(9) 0.016(3) 0.235(13) 0.04(8) 1.000 Uiso H5 0.274(9) 0.039(3) -0.024(14) 0.055 1.000 Uiso H7 0.43764 0.11198 0.14660 0.049 1.000 Uiso H9 0.48418 0.18525 0.21435 0.080 1.000 Uiso H10 0.43403 0.24642 0.41528 0.094 1.000 Uiso H11 0.25452 0.24323 0.69746 0.093 1.000 Uiso H12 0.13088 0.17869 0.79534 0.080 1.000 Uiso H14 0.09540 0.10312 0.73221 0.060 1.000 Uiso H15 0.15024 0.04229 0.53714 0.051 1.000 Uiso H16A 0.58173 0.01937 -0.33134 0.038 1.000 Uiso H16B 0.57833 0.03217 -0.11294 0.038 1.000 Uiso H16C 0.74223 0.02557 -0.21834 0.038 1.000 Uiso H17 0.51801 0.09141 -0.30358 0.041 1.000 Uiso H18A 0.72765 0.11713 -0.51750 0.048 1.000 Uiso H18B 0.65915 0.06823 -0.59090 0.048 1.000 Uiso H18C 0.84415 0.07293 -0.47030 0.048 1.000 Uiso H20 0.86984 0.05824 -0.01526 0.043 1.000 Uiso H21 1.01406 0.10460 0.20662 0.050 1.000 Uiso H22 0.94918 0.17788 0.21893 0.053 1.000 Uiso H24 0.59287 0.16025 -0.22172 0.045 1.000 Uiso H26A 0.59456 0.26527 -0.09618 0.093 1.000 Uiso H26B 0.50656 0.21727 -0.07148 0.093 1.000 Uiso H26C 0.65036 0.22617 -0.25328 0.093 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 0.044(2) 0.047(2) 0.037(2) 0.001(2) 0.001(2) 0.005(2) O3 0.039(2) 0.054(3) 0.042(2) 0.007(2) 0.005(2) 0.002(2) O5 0.056(4) 0.077(3) 0.033(3) 0.004(3) -0.008(3) -0.002(3) O25 0.102(4) 0.042(3) 0.093(4) -0.002(3) -0.025(4) -0.015(3) N16 0.036(3) 0.042(3) 0.036(3) -0.002(2) 0.002(3) -0.001(2) C2 0.034(3) 0.033(3) 0.045(4) -0.005(3) -0.004(3) -0.010(3) C4 0.035(4) 0.043(3) 0.042(4) -0.004(3) -0.003(3) -0.002(3) C6 0.033(3) 0.048(4) 0.042(4) 0.005(3) -0.003(3) 0.006(3) C7 0.046(4) 0.052(4) 0.050(4) 0.005(3) 0.001(4) 0.001(4) C8 0.048(4) 0.049(4) 0.065(5) 0.004(4) -0.005(4) 0.004(4) C9 0.085(6) 0.059(5) 0.097(6) -0.011(5) 0.014(6) -0.001(5) C10 0.104(8) 0.055(5) 0.125(9) -0.003(5) -0.003(8) -0.013(6) C11 0.095(7) 0.060(5) 0.126(8) 0.008(5) -0.022(8) -0.035(6) C12 0.074(6) 0.085(6) 0.082(6) 0.022(5) -0.006(5) -0.031(5) C13 0.043(4) 0.067(5) 0.049(4) 0.009(4) -0.005(4) -0.004(4) C14 0.057(4) 0.082(5) 0.041(4) 0.008(4) 0.015(4) 0.007(4) C15 0.050(4) 0.052(4) 0.050(4) 0.004(3) 0.009(4) 0.007(4) C17 0.039(3) 0.043(3) 0.042(3) 0.004(3) -0.005(3) 0.000(3) C18 0.053(4) 0.052(4) 0.038(4) -0.009(3) -0.005(4) 0.001(3) C19 0.040(3) 0.043(3) 0.033(3) -0.007(3) 0.004(3) 0.001(3) C20 0.044(4) 0.044(3) 0.042(4) -0.001(3) -0.001(4) -0.001(3) C21 0.045(4) 0.061(4) 0.045(4) 0.006(3) -0.003(4) 0.003(4) C22 0.047(4) 0.063(4) 0.050(4) -0.014(4) -0.008(4) -0.006(4) C23 0.062(5) 0.043(4) 0.056(4) -0.004(4) 0.001(5) -0.004(4) C24 0.048(4) 0.044(3) 0.044(4) 0.003(3) -0.008(4) 0.007(3) C26 0.129(8) 0.047(4) 0.102(7) 0.019(5) -0.025(7) 0.013(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(8) . . yes O3 C2 1.241(8) . . yes O5 C4 1.419(9) . . yes O25 C23 1.387(8) . . yes O25 C26 1.425(11) . . yes N16 C17 1.515(8) . . yes C2 C4 1.538(9) . . yes C4 C6 1.519(9) . . yes C6 C7 1.353(9) . . yes C6 C15 1.422(10) . . yes C7 C8 1.444(10) . . yes C8 C9 1.387(11) . . yes C8 C13 1.415(10) . . yes C9 C10 1.372(13) . . yes C10 C11 1.398(16) . . yes C11 C12 1.359(13) . . yes C12 C13 1.457(12) . . yes C13 C14 1.390(11) . . yes C14 C15 1.361(10) . . yes C17 C18 1.521(9) . . yes C17 C19 1.518(9) . . yes C19 C20 1.383(9) . . yes C19 C24 1.407(9) . . yes C20 C21 1.386(10) . . yes C21 C22 1.370(10) . . yes C22 C23 1.391(10) . . yes C23 C24 1.395(10) . . yes O5 H5 0.58(8) . . yes N16 H16A 0.960(5) . . yes N16 H16B 0.960(5) . . yes N16 H16C 0.959(5) . . yes C4 H4 1.08(8) . . yes C7 H7 1.080(7) . . yes C9 H9 1.080(10) . . yes C10 H10 1.081(9) . . yes C11 H11 1.081(10) . . yes C12 H12 1.081(9) . . yes C14 H14 1.080(7) . . yes C15 H15 1.080(7) . . yes C17 H17 1.079(7) . . yes C18 H18A 1.081(7) . . yes C18 H18B 1.079(7) . . yes C18 H18C 1.080(7) . . yes C20 H20 1.080(6) . . yes C21 H21 1.079(7) . . yes C22 H22 1.079(7) . . yes C24 H24 1.080(7) . . yes C26 H26A 1.080(7) . . yes C26 H26B 1.082(10) . . yes C26 H26C 1.081(10) . . 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 C23 O25 C26 119.0(6) . . . yes O1 C2 O3 125.5(6) . . . yes O1 C2 C4 115.4(6) . . . yes O3 C2 C4 119.1(6) . . . yes O5 C4 C2 110.0(6) . . . yes O5 C4 C6 111.7(6) . . . yes C2 C4 C6 110.0(5) . . . yes C4 C6 C7 121.6(6) . . . yes C4 C6 C15 118.1(6) . . . yes C7 C6 C15 120.3(6) . . . yes C6 C7 C8 120.5(7) . . . yes C7 C8 C9 121.2(7) . . . yes C7 C8 C13 117.7(6) . . . yes C9 C8 C13 121.1(7) . . . yes C8 C9 C10 119.2(9) . . . yes C9 C10 C11 121.6(9) . . . yes C10 C11 C12 121.1(9) . . . yes C11 C12 C13 119.0(9) . . . yes C8 C13 C12 118.0(7) . . . yes C8 C13 C14 120.6(7) . . . yes C12 C13 C14 121.4(7) . . . yes C13 C14 C15 120.5(7) . . . yes C6 C15 C14 120.5(6) . . . yes N16 C17 C18 108.6(5) . . . yes N16 C17 C19 111.5(5) . . . yes C18 C17 C19 111.3(5) . . . yes C17 C19 C20 123.6(6) . . . yes C17 C19 C24 116.0(6) . . . yes C20 C19 C24 120.0(6) . . . yes C19 C20 C21 119.9(6) . . . yes C20 C21 C22 121.5(7) . . . yes C21 C22 C23 118.8(7) . . . yes O25 C23 C22 115.9(7) . . . yes O25 C23 C24 122.8(7) . . . yes C22 C23 C24 121.3(6) . . . yes C19 C24 C23 118.6(6) . . . yes C4 O5 H5 103.6(93) . . . yes C17 N16 H16A 111.7(5) . . . yes C17 N16 H16B 109.1(5) . . . yes C17 N16 H16C 109.0(5) . . . yes H16A N16 H16B 109.0(5) . . . yes H16A N16 H16C 109.0(5) . . . yes H16B N16 H16C 109.1(5) . . . yes O5 C4 H4 109.8(49) . . . yes C2 C4 H4 108.4(45) . . . yes C6 C4 H4 106.9(47) . . . yes C6 C7 H7 119.9(6) . . . yes C8 C7 H7 119.7(6) . . . yes C8 C9 H9 119.1(8) . . . yes C10 C9 H9 121.6(8) . . . yes C9 C10 H10 119.1(10) . . . yes C11 C10 H10 119.3(9) . . . yes C10 C11 H11 119.4(9) . . . yes C12 C11 H11 119.5(10) . . . yes C11 C12 H12 120.5(9) . . . yes C13 C12 H12 120.4(8) . . . yes C13 C14 H14 120.1(7) . . . yes C15 C14 H14 119.4(7) . . . yes C6 C15 H15 118.9(6) . . . yes C14 C15 H15 120.6(7) . . . yes N16 C17 H17 109.0(5) . . . yes C18 C17 H17 107.8(6) . . . yes C19 C17 H17 108.6(5) . . . yes C17 C18 H18A 108.3(6) . . . yes C17 C18 H18B 109.8(6) . . . yes C17 C18 H18C 109.7(6) . . . yes H18A C18 H18B 109.9(6) . . . yes H18A C18 H18C 109.9(6) . . . yes H18B C18 H18C 109.2(6) . . . yes C19 C20 H20 119.6(6) . . . yes C21 C20 H20 120.5(6) . . . yes C20 C21 H21 119.4(6) . . . yes C22 C21 H21 119.1(7) . . . yes C21 C22 H22 121.1(7) . . . yes C23 C22 H22 120.0(7) . . . yes C19 C24 H24 121.2(6) . . . yes C23 C24 H24 120.3(6) . . . yes O25 C26 H26A 119.9(8) . . . yes O25 C26 H26B 107.2(7) . . . yes O25 C26 H26C 106.5(8) . . . yes H26A C26 H26B 107.0(9) . . . yes H26A C26 H26C 107.0(8) . . . yes H26B C26 H26C 108.9(8) . . . yes #===END data_rngarpme _chemical_name_systematic ; (R)-1-p-Tolylethylammonium (R)-2-Naphthylglycolate ; _chemical_name_common (R)-2/(R)-3f _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _chemical_formula_moiety 'C21 H23 N1 O3 ' _chemical_formula_weight 337.40 _chemical_melting_point 200.5-208.0 _cell_length_a 8.412(2) _cell_length_b 31.505(6) _cell_length_c 6.869(1) _cell_angle_alpha 90.000000(0) _cell_angle_beta 90.000000(0) _cell_angle_gamma 90.000000(0) _cell_volume 1820.3(6) _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 1.231 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 6.57 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1844 _reflns_number_total 1424 _reflns_number_observed 1380 _reflns_observed_criterion 'refl_observed_if_I_>_0.20_sigma(I)' _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_theta_max 51.24 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.094 _refine_ls_wR_factor_obs 0.091 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1380 _refine_ls_number_parameters 221 _refine_ls_goodness_of_fit_obs 1.321 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.070 _refine_ls_shift/esd_mean 0.0174 _refine_diff_density_min -0.29 _refine_diff_density_max 0.29 _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 -0.03336 _diffrn_orient_matrix_UB_12 0.02368 _diffrn_orient_matrix_UB_13 -0.08785 _diffrn_orient_matrix_UB_21 -0.00627 _diffrn_orient_matrix_UB_22 0.01954 _diffrn_orient_matrix_UB_23 0.11447 _diffrn_orient_matrix_UB_31 0.11393 _diffrn_orient_matrix_UB_32 0.00805 _diffrn_orient_matrix_UB_33 -0.01938 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X+0.5,-Y,+Z+0.5 +X+0.5,-Y+0.5,-Z -X,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' #================================================== # 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 -0.9628(5) -0.5022(2) -0.2780(7) 0.048(3) 1.000 Uij O3 -1.0852(6) -0.4898(2) 0.0031(7) 0.054(3) 1.000 Uij O5 -0.8323(7) -0.4525(2) 0.1601(6) 0.061(3) 1.000 Uij N16 -1.1393(7) -0.4651(2) 0.4019(7) 0.043(3) 1.000 Uij C2 -0.9690(9) -0.4869(2) -0.1087(10) 0.039(4) 1.000 Uij C4 -0.8248(8) -0.4625(2) -0.0437(10) 0.045(4) 1.000 Uij C6 -0.8003(8) -0.4231(2) -0.1655(10) 0.047(5) 1.000 Uij C7 -0.8681(10) -0.3867(3) -0.1234(12) 0.065(5) 1.000 Uij C8 -0.8462(9) -0.3499(3) -0.2555(12) 0.061(5) 1.000 Uij C9 -0.9216(14) -0.3110(3) -0.2230(16) 0.101(8) 1.000 Uij C10 -0.8996(13) -0.2784(3) -0.3507(19) 0.101(8) 1.000 Uij C11 -0.7990(14) -0.2833(3) -0.5178(18) 0.097(8) 1.000 Uij C12 -0.7316(13) -0.3208(3) -0.5551(15) 0.093(8) 1.000 Uij C13 -0.7528(10) -0.3567(3) -0.4205(12) 0.057(5) 1.000 Uij C14 -0.6806(11) -0.3944(3) -0.4568(13) 0.074(6) 1.000 Uij C15 -0.7023(9) -0.4271(2) -0.3344(11) 0.057(5) 1.000 Uij C17 -1.1417(8) -0.4197(2) 0.4566(10) 0.045(4) 1.000 Uij C18 -1.2325(10) -0.4153(2) 0.6501(10) 0.059(5) 1.000 Uij C19 -1.2147(9) -0.3917(2) 0.3017(9) 0.043(4) 1.000 Uij C20 -1.3376(9) -0.4048(2) 0.1809(10) 0.045(4) 1.000 Uij C21 -1.4115(9) -0.3762(3) 0.0585(10) 0.055(5) 1.000 Uij C22 -1.3670(10) -0.3349(3) 0.0485(11) 0.059(5) 1.000 Uij C23 -1.2396(12) -0.3218(3) 0.1708(13) 0.072(6) 1.000 Uij C24 -1.1654(9) -0.3493(2) 0.2953(11) 0.056(5) 1.000 Uij C25 -1.4353(13) -0.3032(3) -0.0913(14) 0.091(3) 1.000 Uiso H4 -0.721(11) -0.482(3) -0.065(16) 0.045 1.000 Uiso H5 -0.910(11) -0.475(3) 0.144(15) 0.063 1.000 Uiso H7 -0.93537 -0.38359 0.00974 0.063 1.000 Uiso H9 -1.00362 -0.30852 -0.10246 0.103 1.000 Uiso H10 -0.95579 -0.24822 -0.32165 0.100 1.000 Uiso H11 -0.78001 -0.25576 -0.60908 0.097 1.000 Uiso H12 -0.66182 -0.32389 -0.68627 0.092 1.000 Uiso H14 -0.60482 -0.39847 -0.58235 0.073 1.000 Uiso H15 -0.64587 -0.45734 -0.36389 0.057 1.000 Uiso H16A -1.09289 -0.48295 0.49972 0.042 1.000 Uiso H16B -1.24689 -0.47405 0.37992 0.042 1.000 Uiso H16C -1.07999 -0.46825 0.28342 0.042 1.000 Uiso H17 -1.02067 -0.40953 0.48128 0.044 1.000 Uiso H18A -1.23315 -0.38222 0.69038 0.059 1.000 Uiso H18B -1.35265 -0.42682 0.63298 0.059 1.000 Uiso H18C -1.17365 -0.43392 0.76088 0.059 1.000 Uiso H20 -1.37704 -0.43739 0.18427 0.045 1.000 Uiso H21 -1.50593 -0.38701 -0.03590 0.053 1.000 Uiso H23 -1.20209 -0.28897 0.16647 0.072 1.000 Uiso H24 -1.06775 -0.33868 0.38509 0.056 1.000 Uiso H25A -1.39958 -0.27033 -0.09835 0.090 1.000 Uiso H25B -1.42018 -0.31583 -0.23635 0.090 1.000 Uiso H25C -1.56028 -0.30313 -0.05535 0.090 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 0.047(3) 0.055(3) 0.041(3) 0.002(2) 0.004(3) -0.003(2) O3 0.053(3) 0.069(4) 0.039(3) 0.000(3) 0.010(3) 0.001(2) O5 0.081(4) 0.069(3) 0.033(3) -0.019(3) -0.004(3) 0.000(2) N16 0.036(3) 0.053(3) 0.039(3) 0.004(3) 0.003(3) 0.000(3) C2 0.045(4) 0.040(4) 0.033(4) 0.004(4) 0.003(4) 0.004(3) C4 0.047(4) 0.046(4) 0.042(4) -0.001(4) -0.004(4) -0.001(4) C6 0.044(4) 0.054(5) 0.044(4) -0.008(4) -0.004(4) 0.000(4) C7 0.062(5) 0.060(5) 0.071(5) -0.001(5) 0.000(5) 0.007(5) C8 0.039(4) 0.072(6) 0.073(6) 0.002(4) -0.003(5) -0.009(5) C9 0.111(8) 0.067(6) 0.126(9) -0.002(6) -0.012(8) -0.024(7) C10 0.110(8) 0.046(5) 0.148(10) -0.016(6) -0.016(9) 0.025(6) C11 0.093(8) 0.085(7) 0.112(8) -0.030(7) -0.016(8) 0.032(7) C12 0.085(7) 0.099(7) 0.095(7) -0.017(6) 0.006(7) 0.016(7) C13 0.040(4) 0.054(5) 0.078(6) -0.004(4) -0.005(5) 0.000(5) C14 0.061(6) 0.099(7) 0.062(5) -0.015(6) 0.007(5) -0.006(6) C15 0.051(5) 0.070(5) 0.050(5) -0.020(4) 0.003(5) 0.003(4) C17 0.033(4) 0.050(4) 0.051(4) -0.003(3) 0.000(4) -0.009(4) C18 0.064(5) 0.076(5) 0.036(4) 0.019(4) -0.001(4) -0.011(4) C19 0.051(4) 0.045(4) 0.033(4) 0.002(4) 0.012(4) 0.002(3) C20 0.046(4) 0.051(4) 0.038(4) -0.012(4) -0.004(4) -0.001(4) C21 0.051(5) 0.067(5) 0.046(4) -0.008(4) -0.005(4) -0.010(4) C22 0.053(5) 0.073(6) 0.050(5) 0.006(4) 0.000(5) 0.018(4) C23 0.084(6) 0.063(5) 0.069(5) 0.000(5) 0.007(6) 0.000(5) C24 0.054(5) 0.053(5) 0.062(5) -0.004(4) -0.003(5) -0.005(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 O1 C2 1.260(9) . . yes O3 C2 1.246(9) . . yes O5 C4 1.436(8) . . yes N16 C17 1.476(9) . . yes C2 C4 1.504(10) . . yes C4 C6 1.513(10) . . yes C6 C7 1.312(11) . . yes C6 C15 1.429(11) . . yes C7 C8 1.483(12) . . yes C8 C9 1.398(13) . . yes C8 C13 1.396(12) . . yes C9 C10 1.364(15) . . yes C10 C11 1.434(18) . . yes C11 C12 1.336(16) . . yes C12 C13 1.471(14) . . yes C13 C14 1.357(13) . . yes C14 C15 1.344(13) . . yes C17 C18 1.539(10) . . yes C17 C19 1.513(10) . . yes C19 C20 1.389(10) . . yes C19 C24 1.399(10) . . yes C20 C21 1.380(11) . . yes C21 C22 1.355(12) . . yes C22 C23 1.423(13) . . yes C22 C25 1.500(13) . . yes C23 C24 1.368(12) . . yes O5 H5 0.96(9) . . yes N16 H16A 0.960(6) . . yes N16 H16B 0.960(6) . . yes N16 H16C 0.960(6) . . yes C4 H4 1.08(10) . . yes C7 H7 1.080(9) . . yes C9 H9 1.080(12) . . yes C10 H10 1.081(10) . . yes C11 H11 1.081(12) . . yes C12 H12 1.080(11) . . yes C14 H14 1.081(9) . . yes C15 H15 1.082(8) . . yes C17 H17 1.081(7) . . yes C18 H18A 1.079(8) . . yes C18 H18B 1.080(9) . . yes C18 H18C 1.080(8) . . yes C20 H20 1.079(7) . . yes C21 H21 1.080(8) . . yes C23 H23 1.081(9) . . yes C24 H24 1.080(8) . . yes C25 H25A 1.080(10) . . yes C25 H25B 1.080(10) . . yes C25 H25C 1.080(11) . . 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(7) . . . yes O1 C2 C4 115.8(6) . . . yes O3 C2 C4 119.2(6) . . . yes O5 C4 C2 111.5(6) . . . yes O5 C4 C6 111.4(6) . . . yes C2 C4 C6 111.4(6) . . . yes C4 C6 C7 122.5(7) . . . yes C4 C6 C15 117.0(7) . . . yes C7 C6 C15 120.5(7) . . . yes C6 C7 C8 119.6(8) . . . yes C7 C8 C9 122.1(8) . . . yes C7 C8 C13 116.6(7) . . . yes C9 C8 C13 121.3(9) . . . yes C8 C9 C10 119.7(10) . . . yes C9 C10 C11 121.0(10) . . . yes C10 C11 C12 119.9(10) . . . yes C11 C12 C13 120.5(10) . . . yes C8 C13 C12 117.5(8) . . . yes C8 C13 C14 122.3(8) . . . yes C12 C13 C14 120.2(9) . . . yes C13 C14 C15 119.8(8) . . . yes C6 C15 C14 121.1(8) . . . yes N16 C17 C18 108.3(6) . . . yes N16 C17 C19 113.0(6) . . . yes C18 C17 C19 110.7(6) . . . yes C17 C19 C20 123.3(6) . . . yes C17 C19 C24 117.4(7) . . . yes C20 C19 C24 119.0(7) . . . yes C19 C20 C21 120.4(7) . . . yes C20 C21 C22 122.2(8) . . . yes C21 C22 C23 117.2(8) . . . yes C21 C22 C25 124.4(8) . . . yes C23 C22 C25 118.2(8) . . . yes C22 C23 C24 121.9(8) . . . yes C19 C24 C23 119.3(8) . . . yes C4 O5 H5 76.2(63) . . . yes C17 N16 H16A 113.3(5) . . . yes C17 N16 H16B 108.2(6) . . . yes C17 N16 H16C 108.9(5) . . . yes H16A N16 H16B 108.7(5) . . . yes H16A N16 H16C 108.7(6) . . . yes H16B N16 H16C 109.0(5) . . . yes O5 C4 H4 107.0(58) . . . yes C2 C4 H4 108.4(50) . . . yes C6 C4 H4 107.0(52) . . . yes C6 C7 H7 119.6(8) . . . yes C8 C7 H7 120.8(8) . . . yes C8 C9 H9 118.4(9) . . . yes C10 C9 H9 121.7(10) . . . yes C9 C10 H10 119.0(12) . . . yes C11 C10 H10 120.0(10) . . . yes C10 C11 H11 117.8(10) . . . yes C12 C11 H11 122.4(11) . . . yes C11 C12 H12 118.1(11) . . . yes C13 C12 H12 121.4(10) . . . yes C13 C14 H14 121.0(9) . . . yes C15 C14 H14 119.2(9) . . . yes C6 C15 H15 118.9(7) . . . yes C14 C15 H15 119.9(8) . . . yes N16 C17 H17 108.3(6) . . . yes C18 C17 H17 107.7(6) . . . yes C19 C17 H17 108.6(6) . . . yes C17 C18 H18A 108.1(7) . . . yes C17 C18 H18B 109.9(6) . . . yes C17 C18 H18C 109.4(7) . . . yes H18A C18 H18B 110.3(8) . . . yes H18A C18 H18C 110.2(7) . . . yes H18B C18 H18C 108.9(7) . . . yes C19 C20 H20 119.9(7) . . . yes C21 C20 H20 119.7(7) . . . yes C20 C21 H21 119.4(8) . . . yes C22 C21 H21 118.4(8) . . . yes C22 C23 H23 118.8(8) . . . yes C24 C23 H23 119.3(9) . . . yes C19 C24 H24 120.1(7) . . . yes C23 C24 H24 120.5(7) . . . yes C22 C25 H25A 124.1(9) . . . yes C22 C25 H25B 107.5(8) . . . yes C22 C25 H25C 103.2(8) . . . yes H25A C25 H25B 106.2(9) . . . yes H25A C25 H25C 106.2(9) . . . yes H25B C25 H25C 109.0(9) . . . yes #===END data_spetsnga _chemical_name_systematic ; (S)-1-p-Ethylphenylethylammonium (S)-2-Naphthylglycolate ; _chemical_name_common (S)-2/(S)-3g _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _chemical_formula_moiety 'C22 H25 N1 O3 ' _chemical_formula_weight 351.40 _chemical_melting_point 203.0-209.5 _cell_length_a 16.625(5) _cell_length_b 6.757(3) _cell_length_c 8.507(3) _cell_angle_alpha 90.000000(0) _cell_angle_beta 91.38(3) _cell_angle_gamma 90.000000(0) _cell_volume 955.3(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 1.222 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 6.45 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1838 _reflns_number_total 1638 _reflns_number_observed 1433 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.067 _diffrn_reflns_theta_max 51.32 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.072 _refine_ls_wR_factor_obs 0.086 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1433 _refine_ls_number_parameters 237 _refine_ls_goodness_of_fit_obs 1.104 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0245 _refine_ls_shift/esd_mean 0.0038 _refine_diff_density_min -0.30 _refine_diff_density_max 0.33 _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 -0.02584 _diffrn_orient_matrix_UB_12 -0.01565 _diffrn_orient_matrix_UB_13 -0.10664 _diffrn_orient_matrix_UB_21 0.05381 _diffrn_orient_matrix_UB_22 0.01297 _diffrn_orient_matrix_UB_23 -0.04904 _diffrn_orient_matrix_UB_31 0.00758 _diffrn_orient_matrix_UB_32 -0.14661 _diffrn_orient_matrix_UB_33 0.00721 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 0.51927(19) -0.27000 0.66756(33) 0.051(2) 1.000 Uij O3 0.49682(18) 0.01694(64) 0.78698(34) 0.045(2) 1.000 Uij O5 0.5879(2) -0.4295(7) 0.9248(5) 0.058(2) 1.000 Uij N16 0.5681(2) -0.6665(7) 0.6095(4) 0.041(2) 1.000 Uij C2 0.5258(3) -0.1555(8) 0.7819(5) 0.038(2) 1.000 Uij C4 0.5718(3) -0.2251(8) 0.9310(5) 0.042(2) 1.000 Uij C6 0.6474(3) -0.1063(9) 0.9511(5) 0.045(2) 1.000 Uij C7 0.6434(4) 0.0741(9) 1.0395(6) 0.063(3) 1.000 Uij C8 0.7084(4) 0.1915(11) 1.0601(7) 0.074(4) 1.000 Uij C9 0.7799(3) 0.1404(9) 0.9881(6) 0.054(3) 1.000 Uij C10 0.8513(4) 0.2736(15) 1.0033(7) 0.093(5) 1.000 Uij C11 0.9217(4) 0.2159(16) 0.9328(8) 0.095(5) 1.000 Uij C12 0.9239(4) 0.0361(17) 0.8511(8) 0.096(5) 1.000 Uij C13 0.8597(4) -0.0848(14) 0.8313(7) 0.085(4) 1.000 Uij C14 0.7889(3) -0.0304(10) 0.9005(5) 0.061(3) 1.000 Uij C15 0.7166(3) -0.1615(11) 0.8838(6) 0.059(3) 1.000 Uij C17 0.6529(3) -0.7299(8) 0.6063(5) 0.047(2) 1.000 Uij C18 0.6595(3) -0.9270(9) 0.5204(6) 0.055(3) 1.000 Uij C19 0.7087(3) -0.5768(8) 0.5306(4) 0.043(2) 1.000 Uij C20 0.7886(3) -0.5800(9) 0.5761(5) 0.052(3) 1.000 Uij C21 0.8431(3) -0.4606(10) 0.5011(7) 0.063(3) 1.000 Uij C22 0.8179(3) -0.3328(9) 0.3781(5) 0.055(3) 1.000 Uij C23 0.7385(3) -0.3317(9) 0.3358(5) 0.049(3) 1.000 Uij C24 0.6837(3) -0.4533(8) 0.4126(5) 0.045(2) 1.000 Uij C25 0.8797(4) -0.2041(12) 0.2975(7) 0.081(4) 1.000 Uij C26 0.9058(7) -0.0285(20) 0.3805(10) 0.154(9) 1.000 Uij H4 0.536(5) -0.195(15) 1.033(10) 0.042 1.000 Uiso H5 0.554(3) -0.431(10) 0.873(7) 0.058 1.000 Uiso H7 0.58724 0.11563 1.09158 0.063 1.000 Uiso H8 0.70480 0.32414 1.13048 0.074 1.000 Uiso H10 0.84884 0.40948 1.06983 0.093 1.000 Uiso H11 0.97438 0.30916 0.93921 0.095 1.000 Uiso H12 0.98048 -0.00998 0.80309 0.096 1.000 Uiso H13 0.86395 -0.21742 0.76109 0.085 1.000 Uiso H15 0.719(3) -0.298(10) 0.818(7) 0.059 1.000 Uiso H16A 0.534(4) -0.761(11) 0.658(7) 0.041 1.000 Uiso H16B 0.550(3) -0.647(9) 0.503(6) 0.041 1.000 Uiso H16C 0.564(3) -0.543(11) 0.665(7) 0.041 1.000 Uiso H17 0.674(4) -0.758(14) 0.725(10) 0.047 1.000 Uiso H18A 0.722(5) -0.973(14) 0.517(8) 0.055 1.000 Uiso H18B 0.636(8) -0.912(24) 0.402(15) 0.05(3) 1.000 Uiso H18C 0.625(8) -1.037(31) 0.581(16) 0.055 1.000 Uiso H20 0.80915 -0.67483 0.67106 0.052 1.000 Uiso H21 0.90598 -0.46719 0.53548 0.063 1.000 Uiso H23 0.717(4) -0.235(12) 0.243(8) 0.049 1.000 Uiso H24 0.62089 -0.44961 0.37721 0.045 1.000 Uiso H25A 0.855(6) -0.163(17) 0.183(11) 0.082 1.000 Uiso H25B 0.93283 -0.29341 0.28206 0.082 1.000 Uiso H26A 0.95008 0.06138 0.32315 0.154 1.000 Uiso H26B 0.93008 -0.07012 0.49465 0.154 1.000 Uiso H26C 0.85268 0.06078 0.39585 0.154 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 0.068(2) 0.038(2) 0.046(2) 0.003(2) 0.005(1) -0.007(1) O3 0.058(2) 0.028(2) 0.049(2) 0.009(2) 0.009(1) -0.004(1) O5 0.064(2) 0.033(2) 0.077(2) -0.003(2) 0.003(2) 0.011(2) N16 0.050(2) 0.029(2) 0.045(2) -0.002(2) 0.010(2) -0.002(2) C2 0.045(2) 0.034(2) 0.037(2) 0.001(2) 0.014(2) -0.004(2) C4 0.056(3) 0.030(2) 0.040(2) 0.005(2) 0.013(2) 0.003(2) C6 0.050(2) 0.042(3) 0.042(2) 0.001(2) 0.000(2) 0.009(2) C7 0.083(4) 0.038(3) 0.068(3) -0.004(3) -0.004(3) -0.004(3) C8 0.093(4) 0.054(3) 0.074(3) 0.011(3) 0.001(3) -0.011(3) C9 0.059(3) 0.054(3) 0.050(2) 0.004(3) -0.001(2) 0.003(2) C10 0.092(4) 0.118(6) 0.068(3) -0.030(5) -0.007(3) 0.005(4) C11 0.071(4) 0.133(7) 0.082(4) -0.039(5) -0.002(3) 0.011(5) C12 0.067(4) 0.135(8) 0.087(4) -0.027(5) -0.008(3) -0.006(5) C13 0.073(4) 0.109(6) 0.073(3) 0.006(4) 0.008(3) -0.015(4) C14 0.069(3) 0.066(4) 0.047(2) 0.009(3) 0.002(2) 0.000(3) C15 0.062(3) 0.064(3) 0.051(2) -0.011(3) 0.001(2) 0.008(3) C17 0.061(3) 0.031(2) 0.047(2) 0.000(2) 0.011(2) 0.006(2) C18 0.069(3) 0.028(2) 0.068(3) 0.002(2) 0.024(2) 0.001(2) C19 0.060(3) 0.033(2) 0.037(2) 0.003(2) 0.008(2) 0.000(2) C20 0.054(3) 0.048(3) 0.055(2) -0.003(2) 0.002(2) 0.012(2) C21 0.045(2) 0.062(4) 0.083(3) 0.005(3) 0.005(2) 0.008(3) C22 0.071(3) 0.046(3) 0.047(2) -0.004(3) 0.018(2) 0.001(2) C23 0.068(3) 0.033(2) 0.045(2) 0.003(2) 0.004(2) 0.004(2) C24 0.054(2) 0.033(3) 0.049(2) 0.002(2) 0.006(2) -0.001(2) C25 0.086(4) 0.076(4) 0.083(4) -0.010(4) 0.037(3) 0.020(3) C26 0.21(1) 0.15(1) 0.10(1) -0.12(1) 0.05(1) -0.01(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 O1 C2 1.245(6) . . yes O3 C2 1.262(7) . . yes O5 C4 1.408(8) . . yes N16 C17 1.474(6) . . yes C2 C4 1.539(6) . . yes C4 C6 1.498(7) . . yes C6 C7 1.435(9) . . yes C6 C15 1.349(7) . . yes C7 C8 1.348(9) . . yes C8 C9 1.394(8) . . yes C9 C10 1.493(10) . . yes C9 C14 1.384(9) . . yes C10 C11 1.383(11) . . yes C11 C12 1.400(15) . . yes C12 C13 1.351(12) . . yes C13 C14 1.380(9) . . yes C14 C15 1.497(9) . . yes C17 C18 1.525(8) . . yes C17 C19 1.541(7) . . yes C19 C20 1.376(7) . . yes C19 C24 1.363(7) . . yes C20 C21 1.380(8) . . yes C21 C22 1.412(8) . . yes C22 C23 1.361(7) . . yes C22 C25 1.522(9) . . yes C23 C24 1.400(7) . . yes C25 C26 1.442(15) . . yes O5 H5 0.71(6) . . yes N16 H16A 0.96(7) . . yes N16 H16B 0.96(5) . . yes N16 H16C 0.96(7) . . yes C4 H4 1.08(9) . . yes C7 H7 1.081(6) . . yes C8 H8 1.080(7) . . yes C10 H10 1.080(10) . . yes C11 H11 1.080(9) . . yes C12 H12 1.081(8) . . yes C13 H13 1.080(9) . . yes C15 H15 1.08(7) . . yes C17 H17 1.08(9) . . yes C18 H18A 1.08(9) . . yes C18 H18B 1.08(14) . . yes C18 H18C 1.08(18) . . yes C20 H20 1.080(6) . . yes C21 H21 1.080(5) . . yes C23 H23 1.08(8) . . yes C24 H24 1.080(5) . . yes C25 H25A 1.08(10) . . yes C25 H25B 1.080(7) . . yes C26 H26A 1.080(12) . . yes C26 H26B 1.080(10) . . yes C26 H26C 1.080(13) . . 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 125.1(4) . . . yes O1 C2 C4 119.1(5) . . . yes O3 C2 C4 115.8(4) . . . yes O5 C4 C2 111.1(4) . . . yes O5 C4 C6 111.7(4) . . . yes C2 C4 C6 109.2(4) . . . yes C4 C6 C7 117.8(5) . . . yes C4 C6 C15 121.7(5) . . . yes C7 C6 C15 120.5(6) . . . yes C6 C7 C8 121.4(6) . . . yes C7 C8 C9 119.1(6) . . . yes C8 C9 C10 119.8(6) . . . yes C8 C9 C14 123.2(6) . . . yes C10 C9 C14 117.0(6) . . . yes C9 C10 C11 118.1(8) . . . yes C10 C11 C12 119.5(8) . . . yes C11 C12 C13 123.8(7) . . . yes C12 C13 C14 117.7(8) . . . yes C9 C14 C13 123.8(6) . . . yes C9 C14 C15 116.6(5) . . . yes C13 C14 C15 119.6(7) . . . yes C6 C15 C14 119.1(6) . . . yes N16 C17 C18 110.0(4) . . . yes N16 C17 C19 113.4(5) . . . yes C18 C17 C19 109.6(4) . . . yes C17 C19 C20 117.3(5) . . . yes C17 C19 C24 122.9(5) . . . yes C20 C19 C24 119.5(5) . . . yes C19 C20 C21 120.1(5) . . . yes C20 C21 C22 121.0(5) . . . yes C21 C22 C23 117.8(5) . . . yes C21 C22 C25 119.5(5) . . . yes C23 C22 C25 122.7(5) . . . yes C22 C23 C24 120.8(5) . . . yes C19 C24 C23 120.9(5) . . . yes C22 C25 C26 116.6(7) . . . yes C4 O5 H5 83.6(57) . . . yes C17 N16 H16A 113.2(41) . . . yes C17 N16 H16B 107.9(33) . . . yes C17 N16 H16C 109.7(33) . . . yes H16A N16 H16B 108.5(50) . . . yes H16A N16 H16C 108.5(54) . . . yes H16B N16 H16C 109.0(53) . . . yes O5 C4 H4 109.0(54) . . . yes C2 C4 H4 109.3(45) . . . yes C6 C4 H4 106.4(47) . . . yes C6 C7 H7 119.1(6) . . . yes C8 C7 H7 119.5(6) . . . yes C7 C8 H8 120.4(6) . . . yes C9 C8 H8 120.6(6) . . . yes C9 C10 H10 121.2(6) . . . yes C11 C10 H10 120.7(8) . . . yes C10 C11 H11 120.5(10) . . . yes C12 C11 H11 120.0(7) . . . yes C11 C12 H12 118.1(8) . . . yes C13 C12 H12 118.1(10) . . . yes C12 C13 H13 120.6(7) . . . yes C14 C13 H13 121.6(7) . . . yes C6 C15 H15 120.3(32) . . . yes C14 C15 H15 120.6(32) . . . yes N16 C17 H17 108.8(42) . . . yes C18 C17 H17 105.8(50) . . . yes C19 C17 H17 108.9(45) . . . yes C17 C18 H18A 110.1(47) . . . yes C17 C18 H18B 109.7(87) . . . yes C17 C18 H18C 109.3(92) . . . yes H18A C18 H18B 109.4(81) . . . yes H18A C18 H18C 109.3(96) . . . yes H18B C18 H18C 109.0(108) . . . yes C19 C20 H20 120.3(5) . . . yes C21 C20 H20 119.6(5) . . . yes C20 C21 H21 119.5(6) . . . yes C22 C21 H21 119.6(6) . . . yes C22 C23 H23 119.5(38) . . . yes C24 C23 H23 119.7(38) . . . yes C19 C24 H24 119.7(5) . . . yes C23 C24 H24 119.4(5) . . . yes C22 C25 H25A 108.2(53) . . . yes C22 C25 H25B 107.3(7) . . . yes C26 C25 H25A 109.1(61) . . . yes C26 C25 H25B 106.4(7) . . . yes H25A C25 H25B 109.0(53) . . . yes C25 C26 H26A 116.2(9) . . . yes C25 C26 H26B 109.1(11) . . . yes C25 C26 H26C 106.4(10) . . . yes H26A C26 H26B 107.9(11) . . . yes H26A C26 H26C 108.0(12) . . . yes H26B C26 H26C 109.0(9) . . . yes #===END data_sngaspcl _chemical_name_systematic ; (S)-1-p-Chlorophenylethylammonium (S)-2-Naphthylglycolate ; _chemical_name_common (S)-2/(S)-3k _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _chemical_formula_moiety 'C20 H20 N1 O3 Cl1 ' _chemical_formula_weight 357.90 _chemical_melting_point 207.0-212.0 _cell_length_a 8.420(2) _cell_length_b 31.089(6) _cell_length_c 6.869(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 90.000000(0) _cell_angle_gamma 90.000000(0) _cell_volume 1798.1(6) _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 1.379 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 20.32 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1827 _reflns_number_total 1690 _reflns_number_observed 1524 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_theta_max 51.50 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.068 _refine_ls_wR_factor_obs 0.065 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1524 _refine_ls_number_parameters 229 _refine_ls_goodness_of_fit_obs 1.241 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.3153 _refine_ls_shift/esd_mean 0.0378 _refine_diff_density_min -0.27 _refine_diff_density_max 0.57 _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 -0.05270 _diffrn_orient_matrix_UB_12 -0.02748 _diffrn_orient_matrix_UB_13 0.03944 _diffrn_orient_matrix_UB_21 0.10195 _diffrn_orient_matrix_UB_22 -0.01025 _diffrn_orient_matrix_UB_23 0.05857 _diffrn_orient_matrix_UB_31 -0.03051 _diffrn_orient_matrix_UB_32 0.01321 _diffrn_orient_matrix_UB_33 0.12729 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X+0.5,-Y,+Z+0.5 +X+0.5,-Y+0.5,-Z -X,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' #================================================== # 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 Cl1 0.4612(3) -0.2012(1) -0.3909(4) 0.098(2) 1.000 Uij O2 0.0874(5) -0.0103(1) -0.5041(7) 0.050(3) 1.000 Uij O3 -0.0358(5) 0.0019(1) -0.2226(6) 0.047(3) 1.000 Uij O4 -0.1655(7) -0.0470(2) -0.6604(9) 0.063(4) 1.000 Uij N5 0.1366(6) -0.0353(2) -0.9029(7) 0.040(3) 1.000 Uij C6 0.1427(8) -0.0817(2) -0.9572(10) 0.045(4) 1.000 Uij C7 -0.0287(8) -0.0132(2) -0.3912(10) 0.039(3) 1.000 Uij C8 0.3408(8) -0.0955(2) -0.6823(10) 0.045(4) 1.000 Uij C9 -0.1776(7) -0.0382(2) -0.4593(9) 0.040(3) 1.000 Uij C10 -0.1981(8) -0.0779(2) -0.3382(10) 0.047(4) 1.000 Uij C11 0.2162(7) -0.1096(2) -0.7997(10) 0.042(3) 1.000 Uij C12 0.4154(8) -0.1236(2) -0.5552(10) 0.051(4) 1.000 Uij C13 0.3664(9) -0.1655(2) -0.5482(11) 0.057(4) 1.000 Uij C14 0.1702(8) -0.1524(2) -0.7892(12) 0.057(4) 1.000 Uij C15 -0.2928(10) -0.0734(3) -0.1681(12) 0.067(5) 1.000 Uij C16 -0.2438(9) -0.1442(2) -0.0743(12) 0.059(5) 1.000 Uij C17 -0.1295(9) -0.1158(2) -0.3805(14) 0.068(5) 1.000 Uij C18 -0.1504(9) -0.1524(2) -0.2387(13) 0.064(5) 1.000 Uij C19 0.2424(9) -0.1805(2) -0.6640(14) 0.065(5) 1.000 Uij C20 0.2306(9) -0.0870(2) -1.1501(11) 0.059(5) 1.000 Uij C21 -0.3178(10) -0.1059(3) -0.0420(14) 0.080(6) 1.000 Uij C22 -0.1941(12) -0.2185(3) 0.0300(19) 0.097(7) 1.000 Uij C23 -0.0806(12) -0.1895(3) -0.2704(20) 0.110(8) 1.000 Uij C24 -0.2665(11) -0.1802(3) 0.0692(18) 0.096(7) 1.000 Uij C25 -0.1055(14) -0.2218(3) -0.1341(21) 0.107(8) 1.000 Uij H4 -0.233(9) -0.049(3) -0.688(14) 0.063 1.000 Uiso H17 -0.06248 -0.11971 -0.51355 0.068 1.000 Uiso H23 -0.00358 -0.19403 -0.39445 0.110 1.000 Uiso H25 -0.05440 -0.25300 -0.16368 0.107 1.000 Uiso H22 -0.20421 -0.24530 0.12946 0.097 1.000 Uiso H24 -0.33799 -0.17580 0.19820 0.096 1.000 Uiso H21 -0.39835 -0.10190 0.07897 0.080 1.000 Uiso H15 -0.34439 -0.04234 -0.13949 0.067 1.000 Uiso H9 -0.28107 -0.01853 -0.43347 0.040 1.000 Uiso H19 0.20374 -0.21362 -0.65485 0.065 1.000 Uiso H14 0.07554 -0.16340 -0.88294 0.057 1.000 Uiso H12 0.50956 -0.11283 -0.46038 0.051 1.000 Uiso H8 0.37725 -0.06224 -0.68920 0.045 1.000 Uiso H5A 0.08889 -0.01745 -1.00122 0.040 1.000 Uiso H5B 0.07659 -0.03225 -0.78492 0.040 1.000 Uiso H5C 0.24299 -0.02535 -0.88072 0.040 1.000 Uiso H6 0.02303 -0.09295 -0.98219 0.045 1.000 Uiso H20A 0.23507 -0.12072 -1.18818 0.059 1.000 Uiso H20B 0.17017 -0.06922 -1.26318 0.059 1.000 Uiso H20C 0.34957 -0.07452 -1.13448 0.059 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 Cl1 0.110(2) 0.080(1) 0.105(2) 0.005(1) -0.025(2) 0.037(1) O2 0.040(2) 0.061(3) 0.049(3) -0.007(2) 0.006(2) -0.005(2) O3 0.047(3) 0.049(2) 0.045(3) -0.003(2) 0.002(2) -0.007(2) O4 0.066(4) 0.085(4) 0.039(3) -0.020(4) -0.014(3) 0.003(3) N5 0.036(3) 0.047(3) 0.036(3) 0.001(2) 0.002(3) 0.001(2) C6 0.041(4) 0.049(4) 0.045(4) -0.004(3) -0.003(3) -0.005(3) C7 0.041(4) 0.031(3) 0.043(4) 0.002(3) 0.000(3) 0.004(3) C8 0.050(4) 0.043(3) 0.043(4) -0.007(3) 0.005(4) 0.000(3) C9 0.032(3) 0.047(3) 0.040(4) -0.004(3) -0.004(3) -0.001(3) C10 0.034(3) 0.059(4) 0.048(4) -0.012(3) -0.010(3) 0.005(3) C11 0.040(3) 0.044(4) 0.041(4) 0.002(3) 0.004(3) -0.003(3) C12 0.054(4) 0.055(4) 0.044(4) -0.006(3) 0.001(4) -0.004(3) C13 0.061(5) 0.052(4) 0.059(5) 0.011(4) 0.005(4) 0.017(4) C14 0.048(4) 0.046(4) 0.078(5) -0.006(3) -0.007(4) -0.010(4) C15 0.076(6) 0.070(5) 0.056(5) -0.030(5) 0.003(5) 0.002(4) C16 0.056(4) 0.046(4) 0.076(5) -0.004(4) -0.016(5) -0.005(4) C17 0.048(4) 0.047(4) 0.110(7) -0.002(4) -0.015(5) 0.004(5) C18 0.050(4) 0.059(5) 0.083(6) 0.001(4) -0.006(5) -0.014(5) C19 0.056(4) 0.047(4) 0.093(6) -0.006(4) -0.001(5) 0.007(4) C20 0.060(5) 0.072(5) 0.046(4) 0.010(4) 0.000(4) -0.004(4) C21 0.067(5) 0.094(6) 0.081(6) -0.013(5) 0.011(5) -0.013(6) C22 0.080(7) 0.074(6) 0.136(10) -0.021(5) -0.022(8) 0.047(7) C23 0.081(7) 0.087(7) 0.163(12) -0.009(6) -0.020(9) -0.022(8) C24 0.064(6) 0.089(6) 0.135(10) -0.021(5) -0.015(7) 0.025(7) C25 0.109(9) 0.055(5) 0.157(11) -0.035(6) -0.035(9) 0.029(7) 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 Cl1 C13 1.743(8) . . yes O2 C7 1.251(8) . . yes O3 C7 1.252(8) . . yes O4 C9 1.412(9) . . yes N5 C6 1.494(8) . . yes C6 C11 1.518(9) . . yes C6 C20 1.526(10) . . yes C7 C9 1.547(9) . . yes C8 C11 1.393(10) . . yes C8 C12 1.386(10) . . yes C9 C10 1.497(10) . . yes C10 C15 1.421(11) . . yes C10 C17 1.345(10) . . yes C11 C14 1.387(9) . . yes C12 C13 1.366(10) . . yes C13 C19 1.393(12) . . yes C14 C19 1.369(11) . . yes C15 C21 1.346(13) . . yes C16 C18 1.400(12) . . yes C16 C21 1.363(12) . . yes C16 C24 1.503(14) . . yes C17 C18 1.508(12) . . yes C18 C23 1.314(13) . . yes C22 C24 1.364(15) . . yes C22 C25 1.355(19) . . yes C23 C25 1.388(17) . . yes O4 H4 0.60(9) . . yes N5 H5A 0.961(5) . . yes N5 H5B 0.960(6) . . yes N5 H5C 0.959(5) . . yes C6 H6 1.080(7) . . yes C8 H8 1.081(6) . . yes C9 H9 1.080(7) . . yes C12 H12 1.080(7) . . yes C14 H14 1.080(8) . . yes C15 H15 1.078(9) . . yes C17 H17 1.081(10) . . yes C19 H19 1.081(7) . . yes C20 H20A 1.081(8) . . yes C20 H20B 1.081(8) . . yes C20 H20C 1.080(8) . . yes C21 H21 1.080(10) . . yes C22 H22 1.081(12) . . yes C23 H23 1.080(13) . . yes C24 H24 1.080(12) . . yes C25 H25 1.080(10) . . 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 N5 C6 C11 112.9(6) . . . yes N5 C6 C20 109.7(6) . . . yes C11 C6 C20 111.1(6) . . . yes O2 C7 O3 125.7(6) . . . yes O2 C7 C9 118.8(6) . . . yes O3 C7 C9 115.4(6) . . . yes C11 C8 C12 120.5(6) . . . yes O4 C9 C7 109.5(6) . . . yes O4 C9 C10 113.1(6) . . . yes C7 C9 C10 109.8(6) . . . yes C9 C10 C15 116.2(7) . . . yes C9 C10 C17 123.5(7) . . . yes C15 C10 C17 120.3(8) . . . yes C6 C11 C8 122.7(6) . . . yes C6 C11 C14 118.1(6) . . . yes C8 C11 C14 118.8(6) . . . yes C8 C12 C13 119.1(7) . . . yes Cl1 C13 C12 119.4(6) . . . yes Cl1 C13 C19 118.9(6) . . . yes C12 C13 C19 121.7(7) . . . yes C11 C14 C19 121.4(7) . . . yes C10 C15 C21 122.9(8) . . . yes C18 C16 C21 123.2(8) . . . yes C18 C16 C24 117.7(7) . . . yes C21 C16 C24 119.1(9) . . . yes C10 C17 C18 118.1(8) . . . yes C16 C18 C17 116.7(7) . . . yes C16 C18 C23 123.0(9) . . . yes C17 C18 C23 120.3(9) . . . yes C13 C19 C14 118.5(7) . . . yes C15 C21 C16 118.6(9) . . . yes C24 C22 C25 118.4(11) . . . yes C18 C23 C25 117.1(11) . . . yes C16 C24 C22 117.6(10) . . . yes C22 C25 C23 126.1(10) . . . yes C9 O4 H4 105.6(93) . . . yes C6 N5 H5A 113.4(5) . . . yes C6 N5 H5B 108.8(5) . . . yes C6 N5 H5C 108.5(5) . . . yes H5A N5 H5B 108.5(5) . . . yes H5A N5 H5C 108.5(5) . . . yes H5B N5 H5C 109.0(5) . . . yes N5 C6 H6 108.6(6) . . . yes C11 C6 H6 108.0(6) . . . yes C20 C6 H6 106.2(6) . . . yes C11 C8 H8 119.3(6) . . . yes C12 C8 H8 120.2(7) . . . yes O4 C9 H9 109.2(6) . . . yes C7 C9 H9 108.6(6) . . . yes C10 C9 H9 106.4(6) . . . yes C8 C12 H12 121.1(7) . . . yes C13 C12 H12 119.8(7) . . . yes C11 C14 H14 118.6(7) . . . yes C19 C14 H14 120.0(7) . . . yes C10 C15 H15 117.6(8) . . . yes C21 C15 H15 119.5(8) . . . yes C10 C17 H17 120.4(8) . . . yes C18 C17 H17 121.5(7) . . . yes C13 C19 H19 120.8(8) . . . yes C14 C19 H19 120.7(8) . . . yes C6 C20 H20A 109.3(7) . . . yes C6 C20 H20B 109.9(7) . . . yes C6 C20 H20C 109.0(7) . . . yes H20A C20 H20B 109.8(7) . . . yes H20A C20 H20C 109.9(7) . . . yes H20B C20 H20C 108.9(7) . . . yes C15 C21 H21 120.5(9) . . . yes C16 C21 H21 120.9(9) . . . yes C24 C22 H22 120.8(12) . . . yes C25 C22 H22 120.7(10) . . . yes C18 C23 H23 120.9(11) . . . yes C25 C23 H23 122.0(10) . . . yes C16 C24 H24 121.0(9) . . . yes C22 C24 H24 121.4(11) . . . yes C22 C25 H25 116.3(11) . . . yes C23 C25 H25 117.5(12) . . . yes #===END data_rngarpome _chemical_name_systematic ; (R)-p-Methoxyphenylethylammonium (R)-2-Naphthylglycolate ; _chemical_name_common (R)-2/(R)-3m _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _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 'C21 H23 N1 O4 ' _chemical_formula_weight 353.40 _chemical_melting_point 166.0-167.5 _cell_length_a 8.673(2) _cell_length_b 31.12(1) _cell_length_c 6.872(2) _cell_angle_alpha 90.000000(0) _cell_angle_beta 90.000000(0) _cell_angle_gamma 90.000000(0) _cell_volume 1855.0(9) _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 1.265 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 7.10 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1877 _reflns_number_total 1655 _reflns_number_observed 1443 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_theta_max 51.41 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.075 _refine_ls_wR_factor_obs 0.072 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1443 _refine_ls_number_parameters 238 _refine_ls_goodness_of_fit_obs 1.098 _refine_ls_weighting_scheme 'Unit' _refine_ls_shift/esd_max 0.2541 _refine_ls_shift/esd_mean 0.0293 _refine_diff_density_min -0.24 _refine_diff_density_max 0.43 _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 -0.10277 _diffrn_orient_matrix_UB_12 -0.01338 _diffrn_orient_matrix_UB_13 -0.02593 _diffrn_orient_matrix_UB_21 -0.00364 _diffrn_orient_matrix_UB_22 -0.01074 _diffrn_orient_matrix_UB_23 0.13703 _diffrn_orient_matrix_UB_31 -0.05222 _diffrn_orient_matrix_UB_32 0.02718 _diffrn_orient_matrix_UB_33 0.04164 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X+0.5,-Y,+Z+0.5 +X+0.5,-Y+0.5,-Z -X,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' #================================================== # 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 0.4627(5) -0.0036(1) 0.2327(6) 0.055(3) 1.000 Uij O3 0.5820(5) 0.0094(1) 0.5113(6) 0.055(3) 1.000 Uij O5 0.3347(10) 0.0458(2) 0.6697(9) 0.078(4) 1.000 Uij O25 0.8730(8) 0.2036(2) 0.4582(11) 0.118(5) 1.000 Uij N16 0.6384(6) 0.0320(2) 0.9142(7) 0.048(3) 1.000 Uij C2 0.4691(7) 0.0121(2) 0.4014(9) 0.049(4) 1.000 Uij C4 0.3263(7) 0.0367(2) 0.4677(9) 0.052(4) 1.000 Uij C6 0.3046(8) 0.0760(2) 0.3457(10) 0.059(4) 1.000 Uij C7 0.3738(10) 0.1137(3) 0.3823(13) 0.082(6) 1.000 Uij C8 0.3477(10) 0.1507(3) 0.2325(14) 0.083(6) 1.000 Uij C9 0.4144(12) 0.1868(4) 0.2601(21) 0.13(1) 1.000 Uij C10 0.3842(15) 0.2193(3) 0.1264(22) 0.13(1) 1.000 Uij C11 0.2917(13) 0.2148(3) -0.0357(19) 0.111(8) 1.000 Uij C12 0.2239(12) 0.1756(3) -0.0723(19) 0.120(9) 1.000 Uij C13 0.2530(9) 0.1402(2) 0.0787(13) 0.072(5) 1.000 Uij C14 0.1805(11) 0.1032(3) 0.0498(15) 0.105(7) 1.000 Uij C15 0.2068(10) 0.0717(3) 0.1794(13) 0.088(6) 1.000 Uij C17 0.6402(7) 0.0774(2) 0.9758(9) 0.051(4) 1.000 Uij C18 0.7296(8) 0.0820(2) 1.1655(10) 0.064(5) 1.000 Uij C19 0.7038(8) 0.1074(2) 0.8219(10) 0.054(4) 1.000 Uij C20 0.8242(8) 0.0979(2) 0.7010(10) 0.059(4) 1.000 Uij C21 0.8863(8) 0.1288(2) 0.5761(10) 0.068(5) 1.000 Uij C22 0.8230(10) 0.1696(2) 0.5768(12) 0.073(5) 1.000 Uij C23 0.7046(11) 0.1794(3) 0.6942(15) 0.091(6) 1.000 Uij C24 0.6462(9) 0.1488(2) 0.8206(12) 0.075(5) 1.000 Uij C26 0.9914(13) 0.1952(4) 0.3360(19) 0.14(1) 1.000 Uij H4 0.22677 0.01650 0.44437 0.052 1.000 Uiso H5 0.348(13) 0.065(2) 0.671(15) 0.078 1.000 Uiso H7 0.44416 0.11806 0.51039 0.082 1.000 Uiso H9 0.49066 0.19194 0.38225 0.133 1.000 Uiso H10 0.43622 0.25054 0.14886 0.132 1.000 Uiso H11 0.27597 0.24145 -0.13498 0.111 1.000 Uiso H12 0.15251 0.17094 -0.19926 0.120 1.000 Uiso H14 0.10433 0.09818 -0.07237 0.105 1.000 Uiso H15 0.14927 0.04131 0.15944 0.088 1.000 Uiso H16A 0.59660 0.01336 1.01236 0.048 1.000 Uiso H16B 0.74240 0.02336 0.88666 0.048 1.000 Uiso H16C 0.57790 0.02926 0.79786 0.048 1.000 Uiso H17 0.52307 0.08711 1.00666 0.051 1.000 Uiso H18A 0.72954 0.11517 1.21102 0.064 1.000 Uiso H18B 0.84644 0.07087 1.14382 0.064 1.000 Uiso H18C 0.67524 0.06217 1.27482 0.064 1.000 Uiso H20 0.87056 0.06570 0.70261 0.059 1.000 Uiso H21 0.97802 0.12040 0.47679 0.068 1.000 Uiso H23 0.65540 0.21134 0.69126 0.091 1.000 Uiso H24 0.55041 0.15608 0.91545 0.075 1.000 Uiso H26A 1.03034 0.22129 0.24468 0.137 1.000 Uiso H26B 0.95684 0.16899 0.24268 0.137 1.000 Uiso H26C 1.087(14) 0.185(2) 0.425(16) 0.137 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 0.055(3) 0.068(3) 0.041(2) 0.004(2) -0.005(2) -0.006(2) O3 0.047(2) 0.075(3) 0.043(2) 0.004(2) -0.006(2) 0.001(2) O5 0.096(4) 0.092(4) 0.047(3) 0.011(4) 0.013(3) 0.000(4) O25 0.126(5) 0.088(4) 0.140(6) 0.002(4) 0.045(6) 0.018(4) N16 0.046(3) 0.062(3) 0.037(3) -0.006(3) -0.002(3) 0.004(3) C2 0.040(3) 0.059(4) 0.047(4) -0.006(3) -0.005(3) 0.005(3) C4 0.044(3) 0.070(4) 0.044(4) 0.000(3) 0.002(3) -0.005(3) C6 0.045(4) 0.078(5) 0.054(4) 0.017(4) 0.008(4) -0.004(4) C7 0.072(5) 0.081(5) 0.094(6) 0.014(5) 0.021(5) 0.009(5) C8 0.063(5) 0.077(5) 0.109(7) -0.002(4) 0.015(5) -0.036(5) C9 0.092(7) 0.137(9) 0.171(13) 0.003(7) 0.005(9) -0.072(10) C10 0.14(1) 0.07(1) 0.18(1) 0.05(1) 0.04(1) 0.04(1) C11 0.116(9) 0.088(7) 0.128(9) 0.014(7) 0.007(8) 0.027(7) C12 0.103(7) 0.111(7) 0.147(10) 0.026(7) 0.022(8) 0.011(8) C13 0.067(5) 0.059(4) 0.090(6) 0.002(4) 0.003(5) -0.016(5) C14 0.094(7) 0.121(8) 0.099(7) 0.024(6) -0.016(6) -0.016(7) C15 0.084(6) 0.109(7) 0.069(5) 0.048(5) -0.001(5) 0.010(5) C17 0.050(3) 0.057(4) 0.047(3) -0.005(3) 0.005(3) -0.002(3) C18 0.075(5) 0.075(5) 0.043(4) -0.016(4) -0.006(4) -0.004(4) C19 0.058(4) 0.056(4) 0.046(3) -0.010(3) -0.004(4) -0.002(3) C20 0.064(4) 0.059(4) 0.053(4) -0.008(4) 0.006(4) -0.006(3) C21 0.060(4) 0.092(5) 0.051(4) -0.002(4) 0.010(4) -0.005(4) C22 0.090(6) 0.053(4) 0.077(5) -0.007(4) 0.011(5) 0.010(4) C23 0.096(6) 0.070(5) 0.106(7) 0.009(5) 0.011(7) 0.007(5) C24 0.079(5) 0.062(4) 0.083(5) -0.005(4) 0.021(5) -0.008(4) C26 0.124(9) 0.141(9) 0.145(11) 0.000(7) 0.066(10) 0.007(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 1.259(8) . . yes O3 C2 1.240(8) . . yes O5 C4 1.419(9) . . yes O25 C22 1.406(10) . . yes O25 C26 1.353(15) . . yes N16 C17 1.477(8) . . yes C2 C4 1.525(9) . . yes C4 C6 1.495(10) . . yes C6 C7 1.341(11) . . yes C6 C15 1.429(11) . . yes C7 C8 1.561(13) . . yes C8 C9 1.280(15) . . yes C8 C13 1.377(13) . . yes C9 C10 1.392(19) . . yes C10 C11 1.380(19) . . yes C11 C12 1.378(16) . . yes C12 C13 1.535(15) . . yes C13 C14 1.327(13) . . yes C14 C15 1.343(14) . . yes C17 C18 1.524(10) . . yes C17 C19 1.514(9) . . yes C19 C20 1.366(10) . . yes C19 C24 1.383(10) . . yes C20 C21 1.397(10) . . yes C21 C22 1.382(11) . . yes C22 C23 1.342(13) . . yes C23 C24 1.387(12) . . yes O5 H5 0.60(8) . . yes N16 H16A 0.960(5) . . yes N16 H16B 0.960(5) . . yes N16 H16C 0.960(5) . . yes C4 H4 1.080(7) . . yes C7 H7 1.080(9) . . yes C9 H9 1.080(14) . . yes C10 H10 1.082(11) . . yes C11 H11 1.081(12) . . yes C12 H12 1.080(13) . . yes C14 H14 1.080(11) . . yes C15 H15 1.078(9) . . yes C17 H17 1.081(7) . . yes C18 H18A 1.080(8) . . yes C18 H18B 1.081(8) . . yes C18 H18C 1.080(8) . . yes C20 H20 1.080(7) . . yes C21 H21 1.080(8) . . yes C23 H23 1.081(9) . . yes C24 H24 1.080(9) . . yes C26 H26A 1.080(12) . . yes C26 H26B 1.080(12) . . yes C26 H26C 1.08(12) . . 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 C22 O25 C26 116.6(8) . . . yes O1 C2 O3 124.6(6) . . . yes O1 C2 C4 115.7(6) . . . yes O3 C2 C4 119.6(6) . . . yes O5 C4 C2 110.5(6) . . . yes O5 C4 C6 113.1(6) . . . yes C2 C4 C6 110.2(6) . . . yes C4 C6 C7 123.6(7) . . . yes C4 C6 C15 116.5(7) . . . yes C7 C6 C15 119.8(8) . . . yes C6 C7 C8 117.2(8) . . . yes C7 C8 C9 119.0(10) . . . yes C7 C8 C13 114.7(7) . . . yes C9 C8 C13 126.3(10) . . . yes C8 C9 C10 117.2(12) . . . yes C9 C10 C11 124.7(11) . . . yes C10 C11 C12 119.0(11) . . . yes C11 C12 C13 116.3(11) . . . yes C8 C13 C12 116.5(8) . . . yes C8 C13 C14 127.0(9) . . . yes C12 C13 C14 116.4(9) . . . yes C13 C14 C15 117.0(10) . . . yes C6 C15 C14 124.2(9) . . . yes N16 C17 C18 109.9(5) . . . yes N16 C17 C19 113.2(5) . . . yes C18 C17 C19 110.8(6) . . . yes C17 C19 C20 124.8(6) . . . yes C17 C19 C24 116.5(7) . . . yes C20 C19 C24 118.3(7) . . . yes C19 C20 C21 121.3(7) . . . yes C20 C21 C22 118.4(7) . . . yes O25 C22 C21 124.6(8) . . . yes O25 C22 C23 114.3(7) . . . yes C21 C22 C23 121.1(8) . . . yes C22 C23 C24 119.9(8) . . . yes C19 C24 C23 120.9(8) . . . yes C4 O5 H5 102.5(102) . . . yes C17 N16 H16A 112.3(5) . . . yes C17 N16 H16B 108.3(5) . . . yes C17 N16 H16C 109.2(5) . . . yes H16A N16 H16B 109.0(5) . . . yes H16A N16 H16C 109.0(5) . . . yes H16B N16 H16C 109.0(5) . . . yes O5 C4 H4 107.6(6) . . . yes C2 C4 H4 108.2(6) . . . yes C6 C4 H4 107.0(6) . . . yes C6 C7 H7 121.1(8) . . . yes C8 C7 H7 121.7(8) . . . yes C8 C9 H9 121.4(13) . . . yes C10 C9 H9 121.4(12) . . . yes C9 C10 H10 118.7(13) . . . yes C11 C10 H10 116.7(11) . . . yes C10 C11 H11 120.3(10) . . . yes C12 C11 H11 120.6(12) . . . yes C11 C12 H12 120.8(11) . . . yes C13 C12 H12 122.9(10) . . . yes C13 C14 H14 122.1(10) . . . yes C15 C14 H14 120.9(10) . . . yes C6 C15 H15 117.3(8) . . . yes C14 C15 H15 118.5(9) . . . yes N16 C17 H17 108.3(5) . . . yes C18 C17 H17 106.5(6) . . . yes C19 C17 H17 107.9(6) . . . yes C17 C18 H18A 109.7(6) . . . yes C17 C18 H18B 109.2(6) . . . yes C17 C18 H18C 108.6(6) . . . yes H18A C18 H18B 110.3(7) . . . yes H18A C18 H18C 110.1(7) . . . yes H18B C18 H18C 108.8(7) . . . yes C19 C20 H20 118.6(7) . . . yes C21 C20 H20 120.1(7) . . . yes C20 C21 H21 120.4(7) . . . yes C22 C21 H21 121.1(7) . . . yes C22 C23 H23 120.1(9) . . . yes C24 C23 H23 120.0(9) . . . yes C19 C24 H24 118.1(7) . . . yes C23 C24 H24 121.0(7) . . . yes O25 C26 H26A 116.8(10) . . . yes O25 C26 H26B 107.7(10) . . . yes O25 C26 H26C 107.0(61) . . . yes H26A C26 H26B 108.0(12) . . . yes H26A C26 H26C 108.1(54) . . . yes H26B C26 H26C 109.0(46) . . . yes #===END data_rngaspme _chemical_name_systematic ; (S)-p-Tolylethylammonium (R)-2-Naphthylglycolate ; _chemical_name_common (R)-2/(S)-3f _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _chemical_formula_moiety 'C21 H23 N1 O3 ' _chemical_formula_weight 339.40 _chemical_melting_point 154.5-159.5 deg _cell_length_a 33.84(1) _cell_length_b 5.952(3) _cell_length_c 9.227(3) _cell_angle_alpha 90.000000(0) _cell_angle_beta 93.36(3) _cell_angle_gamma 90.000000(0) _cell_volume 1855(1) _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 1.215 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 6.44 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1784 _reflns_number_total 1615 _reflns_number_observed 1471 _reflns_observed_criterion 'refl_observed_if_I_>_1.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_theta_max 51.41 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -6 _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 0.059 _refine_ls_wR_factor_obs 0.073 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1471 _refine_ls_number_parameters 228 _refine_ls_goodness_of_fit_obs 1.295 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.0817 _refine_ls_shift/esd_mean 0.0106 _refine_diff_density_min -0.23 _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 -0.00192 _diffrn_orient_matrix_UB_12 -0.03769 _diffrn_orient_matrix_UB_13 0.10493 _diffrn_orient_matrix_UB_21 -0.02620 _diffrn_orient_matrix_UB_22 -0.07320 _diffrn_orient_matrix_UB_23 -0.02302 _diffrn_orient_matrix_UB_31 0.01367 _diffrn_orient_matrix_UB_32 -0.14654 _diffrn_orient_matrix_UB_33 -0.01563 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 0.21688(6) 0.32040 0.61475(22) 0.045(1) 1.000 Uij O3 0.22165(8) 0.61231(60) 0.76647(25) 0.049(1) 1.000 Uij O5 0.24510(8) 0.33102(58) 0.98031(26) 0.051(1) 1.000 Uij N16 0.21036(7) -0.12000(63) 0.52228(26) 0.039(1) 1.000 Uij C2 0.21907(10) 0.40318(79) 0.74030(36) 0.042(2) 1.000 Uij C4 0.21817(10) 0.24472(72) 0.86930(33) 0.041(2) 1.000 Uij C6 0.17666(10) 0.22327(84) 0.91754(34) 0.045(2) 1.000 Uij C7 0.16033(11) 0.38247(90) 0.99881(38) 0.055(2) 1.000 Uij C8 0.12098(12) 0.35828(92) 1.04715(39) 0.059(2) 1.000 Uij C9 0.10389(14) 0.51481(113) 1.13502(50) 0.078(3) 1.000 Uij C10 0.06717(16) 0.47968(149) 1.18431(62) 0.096(4) 1.000 Uij C11 0.04492(16) 0.29023(141) 1.14320(70) 0.101(4) 1.000 Uij C12 0.05984(14) 0.13736(120) 1.05670(58) 0.087(4) 1.000 Uij C13 0.09961(12) 0.16409(87) 1.00398(43) 0.059(2) 1.000 Uij C14 0.11678(13) 0.00095(100) 0.92022(46) 0.070(3) 1.000 Uij C15 0.15443(12) 0.02837(88) 0.87792(41) 0.060(2) 1.000 Uij C17 0.17716(10) -0.16674(81) 0.40899(33) 0.048(2) 1.000 Uij C18 0.17807(12) 0.01150(118) 0.29305(42) 0.073(3) 1.000 Uij C19 0.13840(10) -0.19648(80) 0.48042(36) 0.049(2) 1.000 Uij C20 0.13126(12) -0.38790(94) 0.55733(44) 0.061(2) 1.000 Uij C21 0.09559(13) -0.42113(109) 0.62369(45) 0.076(3) 1.000 Uij C22 0.06661(12) -0.26377(126) 0.61547(52) 0.080(3) 1.000 Uij C23 0.07338(13) -0.07116(113) 0.53574(64) 0.084(3) 1.000 Uij C24 0.10848(12) -0.03396(92) 0.47118(51) 0.068(3) 1.000 Uij C25 0.02850(17) -0.30223(185) 0.68894(65) 0.123(5) 1.000 Uij H4 0.2283(10) 0.0809(78) 0.8374(37) 0.041 1.000 Uiso H5 0.2520(10) 0.2247(78) 1.0828(36) 0.051 1.000 Uiso H7 0.17733 0.53077 1.02871 0.055 1.000 Uiso H9 0.12029 0.66481 1.16552 0.078 1.000 Uiso H10 0.05417 0.60408 1.25231 0.096 1.000 Uiso H11 0.01612 0.26393 1.18520 0.101 1.000 Uiso H12 0.04244 -0.00744 1.02311 0.086 1.000 Uiso H14 0.09998 -0.14665 0.88712 0.069 1.000 Uiso H15 0.16783 -0.10013 0.81432 0.059 1.000 Uiso H16A 0.23496 -0.10170 0.47698 0.039 1.000 Uiso H16B 0.21256 -0.24250 0.58998 0.039 1.000 Uiso H16C 0.20436 0.01500 0.57358 0.039 1.000 Uiso H17 0.18386 -0.31864 0.35139 0.047 1.000 Uiso H18A 0.15457 -0.02310 0.21155 0.073 1.000 Uiso H18B 0.20627 0.01280 0.24435 0.073 1.000 Uiso H18C 0.17327 0.17290 0.34265 0.073 1.000 Uiso H20 0.15386 -0.51620 0.56573 0.061 1.000 Uiso H21 0.09109 -0.57383 0.68369 0.076 1.000 Uiso H23 0.05318 0.04204 0.52794 0.084 1.000 Uiso H24 0.11238 0.10174 0.41768 0.068 1.000 Uiso H25A 0.02340 -0.45393 0.74934 0.123 1.000 Uiso H25B 0.00460 -0.28933 0.60634 0.123 1.000 Uiso H25C 0.02650 -0.16403 0.76394 0.123 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 0.062(1) 0.038(1) 0.036(1) -0.002(1) 0.006(1) -0.004(1) O3 0.072(2) 0.035(2) 0.040(1) 0.001(1) 0.004(1) 0.002(1) O5 0.060(1) 0.047(1) 0.046(1) -0.006(1) -0.007(1) 0.004(1) N16 0.049(1) 0.033(2) 0.036(1) -0.001(1) 0.007(1) 0.007(1) C2 0.043(2) 0.038(2) 0.045(2) 0.002(2) 0.005(1) -0.003(2) C4 0.055(2) 0.034(2) 0.034(2) -0.003(2) -0.002(1) 0.000(1) C6 0.052(2) 0.047(2) 0.036(2) 0.000(2) 0.002(1) 0.012(2) C7 0.063(2) 0.053(2) 0.048(2) 0.000(2) 0.005(2) 0.007(2) C8 0.072(2) 0.056(3) 0.048(2) 0.006(2) 0.001(2) 0.004(2) C9 0.082(3) 0.071(3) 0.080(3) 0.006(3) 0.011(2) -0.013(3) C10 0.074(3) 0.116(5) 0.099(4) 0.010(4) 0.024(3) -0.010(4) C11 0.074(3) 0.120(6) 0.109(4) 0.008(4) 0.033(3) -0.012(4) C12 0.073(3) 0.093(4) 0.093(3) -0.008(3) 0.011(3) -0.008(3) C13 0.064(2) 0.061(3) 0.052(2) -0.011(2) 0.002(2) 0.003(2) C14 0.076(3) 0.065(3) 0.067(2) -0.016(3) 0.004(2) -0.007(2) C15 0.068(2) 0.055(3) 0.055(2) -0.004(2) 0.007(2) -0.005(2) C17 0.053(2) 0.047(2) 0.043(2) -0.005(2) 0.003(1) -0.002(2) C18 0.063(2) 0.104(4) 0.052(2) -0.017(3) -0.006(2) 0.029(3) C19 0.049(2) 0.051(2) 0.046(2) -0.004(2) -0.002(1) -0.004(2) C20 0.061(2) 0.057(3) 0.064(2) -0.010(2) 0.001(2) 0.005(2) C21 0.073(3) 0.089(4) 0.067(3) -0.028(3) 0.010(2) 0.014(3) C22 0.049(2) 0.112(5) 0.078(3) -0.020(3) 0.008(2) -0.011(3) C23 0.051(2) 0.092(4) 0.109(4) 0.013(3) 0.007(2) -0.002(3) C24 0.062(2) 0.056(3) 0.086(3) 0.005(2) 0.000(2) 0.010(2) C25 0.076(3) 0.182(9) 0.112(4) -0.030(5) 0.028(3) -0.008(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 1.257(5) . . yes O3 C2 1.270(6) . . yes O5 C4 1.426(5) . . yes N16 C17 1.515(5) . . yes C2 C4 1.520(6) . . yes C4 C6 1.503(5) . . yes C6 C7 1.347(7) . . yes C6 C15 1.419(7) . . yes C7 C8 1.436(6) . . yes C8 C9 1.384(8) . . yes C8 C13 1.408(7) . . yes C9 C10 1.364(8) . . yes C10 C11 1.396(11) . . yes C11 C12 1.329(10) . . yes C12 C13 1.466(7) . . yes C13 C14 1.389(7) . . yes C14 C15 1.364(6) . . yes C17 C18 1.508(7) . . yes C17 C19 1.512(5) . . yes C19 C20 1.371(7) . . yes C19 C24 1.399(7) . . yes C20 C21 1.399(7) . . yes C21 C22 1.355(9) . . yes C22 C23 1.388(10) . . yes C22 C25 1.509(8) . . yes C23 C24 1.377(7) . . yes O5 H5 1.15(4) . . yes N16 H16A 0.959(3) . . yes N16 H16B 0.960(4) . . yes N16 H16C 0.960(4) . . yes C4 H4 1.08(5) . . yes C7 H7 1.081(5) . . yes C9 H9 1.080(7) . . yes C10 H10 1.081(8) . . yes C11 H11 1.081(6) . . yes C12 H12 1.079(7) . . yes C14 H14 1.081(6) . . yes C15 H15 1.080(5) . . yes C17 H17 1.080(5) . . yes C18 H18A 1.082(5) . . yes C18 H18B 1.078(5) . . yes C18 H18C 1.080(7) . . yes C20 H20 1.080(5) . . yes C21 H21 1.080(6) . . yes C23 H23 0.959(6) . . yes C24 H24 0.960(6) . . yes C25 H25A 1.080(10) . . yes C25 H25B 1.081(6) . . yes C25 H25C 1.080(10) . . 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 124.0(4) . . . yes O1 C2 C4 118.4(4) . . . yes O3 C2 C4 117.6(4) . . . yes O5 C4 C2 107.3(4) . . . yes O5 C4 C6 112.7(3) . . . yes C2 C4 C6 110.3(3) . . . yes C4 C6 C7 121.7(4) . . . yes C4 C6 C15 118.9(4) . . . yes C7 C6 C15 119.3(4) . . . yes C6 C7 C8 121.4(5) . . . yes C7 C8 C9 122.8(5) . . . yes C7 C8 C13 117.7(5) . . . yes C9 C8 C13 119.5(5) . . . yes C8 C9 C10 120.8(6) . . . yes C9 C10 C11 121.4(7) . . . yes C10 C11 C12 119.9(6) . . . yes C11 C12 C13 120.9(6) . . . yes C8 C13 C12 117.5(5) . . . yes C8 C13 C14 120.4(4) . . . yes C12 C13 C14 122.0(5) . . . yes C13 C14 C15 120.2(5) . . . yes C6 C15 C14 120.9(5) . . . yes N16 C17 C18 108.4(4) . . . yes N16 C17 C19 110.3(3) . . . yes C18 C17 C19 116.5(4) . . . yes C17 C19 C20 120.4(4) . . . yes C17 C19 C24 122.4(4) . . . yes C20 C19 C24 117.2(4) . . . yes C19 C20 C21 121.8(5) . . . yes C20 C21 C22 121.2(6) . . . yes C21 C22 C23 117.3(5) . . . yes C21 C22 C25 120.3(7) . . . yes C23 C22 C25 122.4(6) . . . yes C22 C23 C24 122.4(6) . . . yes C19 C24 C23 120.1(5) . . . yes C4 O5 H5 118.9(21) . . . yes C17 N16 H16A 110.3(3) . . . yes C17 N16 H16B 109.6(4) . . . yes C17 N16 H16C 108.9(3) . . . yes H16A N16 H16B 109.5(3) . . . yes H16A N16 H16C 109.5(4) . . . yes H16B N16 H16C 109.0(3) . . . yes O5 C4 H4 108.8(19) . . . yes C2 C4 H4 109.0(20) . . . yes C6 C4 H4 108.7(20) . . . yes C6 C7 H7 119.2(4) . . . yes C8 C7 H7 119.5(5) . . . yes C8 C9 H9 118.9(5) . . . yes C10 C9 H9 120.3(6) . . . yes C9 C10 H10 119.9(8) . . . yes C11 C10 H10 118.7(6) . . . yes C10 C11 H11 120.2(7) . . . yes C12 C11 H11 119.9(7) . . . yes C11 C12 H12 119.9(5) . . . yes C13 C12 H12 119.2(6) . . . yes C13 C14 H14 119.7(5) . . . yes C15 C14 H14 120.1(5) . . . yes C6 C15 H15 119.1(4) . . . yes C14 C15 H15 120.0(5) . . . yes N16 C17 H17 109.0(4) . . . yes C18 C17 H17 103.1(4) . . . yes C19 C17 H17 109.2(4) . . . yes C17 C18 H18A 108.3(5) . . . yes C17 C18 H18B 110.9(5) . . . yes C17 C18 H18C 108.4(4) . . . yes H18A C18 H18B 110.1(4) . . . yes H18A C18 H18C 109.9(5) . . . yes H18B C18 H18C 109.2(6) . . . yes C19 C20 H20 118.6(4) . . . yes C21 C20 H20 119.6(5) . . . yes C20 C21 H21 119.6(5) . . . yes C22 C21 H21 119.2(5) . . . yes C22 C23 H23 118.7(5) . . . yes C24 C23 H23 118.9(6) . . . yes C19 C24 H24 119.5(4) . . . yes C23 C24 H24 120.4(5) . . . yes C22 C25 H25A 121.7(8) . . . yes C22 C25 H25B 107.2(5) . . . yes C22 C25 H25C 105.1(7) . . . yes H25A C25 H25B 106.7(8) . . . yes H25A C25 H25C 106.8(6) . . . yes H25B C25 H25C 109.0(8) . . . yes #===END data_sngarpet _chemical_name_systematic ; (R)-p-Ethylphenylethylammonium (S)-2-Naphthylglycolate ; _chemical_name_common (S)-2/(R)-3g _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.15 _chemical_formula_moiety 'C22 H25 O3 N1 ' _chemical_formula_weight 351.40 _chemical_melting_point 177.0-181.5 deg _cell_length_a 16.81(1) _cell_length_b 6.430(2) _cell_length_c 8.945(4) _cell_angle_alpha 90.000000(0) _cell_angle_beta 95.80(4) _cell_angle_gamma 90.000000(0) _cell_volume 961.7(8) _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 1.213 _exptl_crystal_density_meas 1.213 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 6.40 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1829 _reflns_number_total 1362 _reflns_number_observed 1362 _reflns_observed_criterion 'refl_observed_if_I_>_0.0_sigma(I)' _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_theta_max 50.97 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _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 0.098 _refine_ls_wR_factor_obs 0.099 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1362 _refine_ls_number_parameters 224 _refine_ls_goodness_of_fit_obs 1.216 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.2645 _refine_ls_shift/esd_mean 0.0344 _refine_diff_density_min -0.25 _refine_diff_density_max 0.26 _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 -0.03554 _diffrn_orient_matrix_UB_12 -0.05168 _diffrn_orient_matrix_UB_13 -0.08869 _diffrn_orient_matrix_UB_21 0.02817 _diffrn_orient_matrix_UB_22 0.09260 _diffrn_orient_matrix_UB_23 -0.06741 _diffrn_orient_matrix_UB_31 0.03897 _diffrn_orient_matrix_UB_32 -0.11370 _diffrn_orient_matrix_UB_33 -0.01480 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 0.5310(3) 0.5383 0.1758(4) 0.065(2) 1.000 Uij O3 0.5053(2) 0.2300(9) 0.2676(3) 0.057(2) 1.000 Uij O5 0.5326(2) 0.4153(9) 0.5531(3) 0.068(2) 1.000 Uij N16 0.5720(3) 0.9359(9) 0.0824(4) 0.051(3) 1.000 Uij C2 0.5339(3) 0.4133(11) 0.2804(6) 0.050(3) 1.000 Uij C4 0.5786(3) 0.4677(10) 0.4319(5) 0.053(3) 1.000 Uij C6 0.6572(3) 0.3528(12) 0.4513(5) 0.056(4) 1.000 Uij C7 0.7223(3) 0.4195(12) 0.3856(6) 0.063(4) 1.000 Uij C8 0.7946(4) 0.2933(12) 0.3902(6) 0.065(4) 1.000 Uij C9 0.8621(4) 0.3631(14) 0.3256(7) 0.085(5) 1.000 Uij C10 0.9292(4) 0.2481(17) 0.3360(8) 0.094(6) 1.000 Uij C11 0.9315(4) 0.0532(16) 0.4106(8) 0.088(5) 1.000 Uij C12 0.8696(4) -0.0175(14) 0.4756(7) 0.082(5) 1.000 Uij C13 0.7963(3) 0.1033(13) 0.4682(6) 0.064(4) 1.000 Uij C14 0.7296(4) 0.0385(13) 0.5336(7) 0.081(5) 1.000 Uij C15 0.6620(4) 0.1578(13) 0.5256(6) 0.069(4) 1.000 Uij C17 0.6568(3) 1.0060(10) 0.0853(5) 0.053(3) 1.000 Uij C18 0.6573(4) 1.2190(11) 0.0051(7) 0.073(4) 1.000 Uij C19 0.7105(3) 0.8498(10) 0.0157(5) 0.051(3) 1.000 Uij C20 0.7895(4) 0.8495(12) 0.0681(6) 0.062(4) 1.000 Uij C21 0.8443(3) 0.7270(13) -0.0040(7) 0.072(4) 1.000 Uij C22 0.8181(4) 0.6061(11) -0.1276(6) 0.066(4) 1.000 Uij C23 0.7384(4) 0.6044(11) -0.1780(6) 0.061(4) 1.000 Uij C24 0.6830(3) 0.7294(11) -0.1075(5) 0.055(3) 1.000 Uij C25 0.8756(4) 0.4766(15) -0.2040(8) 0.092(2) 1.000 Uiso C26 0.8980(6) 0.2688(21) -0.1315(11) 0.135(3) 1.000 Uiso H4 0.592(4) 0.632(13) 0.435(8) 0.052 1.000 Uiso H5 0.480(4) 0.393(14) 0.502(9) 0.069 1.000 Uiso H7 0.72007 0.56605 0.32640 0.062 1.000 Uiso H9 0.85868 0.50873 0.26506 0.086 1.000 Uiso H10 0.98118 0.30317 0.28596 0.095 1.000 Uiso H11 0.98579 -0.03720 0.41458 0.090 1.000 Uiso H12 0.87329 -0.16428 0.53456 0.082 1.000 Uiso H14 0.73183 -0.10589 0.59554 0.080 1.000 Uiso H15 0.61007 0.10018 0.57438 0.068 1.000 Uiso H16A 0.53875 1.03405 0.12773 0.050 1.000 Uiso H16B 0.57055 0.80615 0.13523 0.050 1.000 Uiso H16C 0.55075 0.91535 -0.02017 0.050 1.000 Uiso H17 0.68083 1.02913 0.20066 0.052 1.000 Uiso H18A 0.71890 1.26751 0.00684 0.072 1.000 Uiso H18B 0.62390 1.33011 0.06444 0.072 1.000 Uiso H18C 0.63020 1.20621 -0.10926 0.072 1.000 Uiso H20 0.81048 0.94384 0.16399 0.060 1.000 Uiso H21 0.90693 0.72641 0.03736 0.070 1.000 Uiso H23 0.71696 0.50824 -0.27249 0.062 1.000 Uiso H24 0.62060 0.73229 -0.15092 0.055 1.000 Uiso H25A 0.93073 0.56347 -0.20088 0.091 1.000 Uiso H25B 0.85283 0.45067 -0.31978 0.091 1.000 Uiso H26A 0.94088 0.17581 -0.18383 0.146 1.000 Uiso H26B 0.84278 0.18201 -0.13463 0.146 1.000 Uiso H26C 0.92078 0.29471 -0.01573 0.146 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 0.102(3) 0.039(2) 0.053(2) -0.003(2) 0.013(2) 0.010(2) O3 0.075(2) 0.043(2) 0.054(2) -0.008(2) 0.019(2) -0.002(2) O5 0.094(3) 0.060(3) 0.049(2) -0.004(2) 0.023(2) 0.002(2) N16 0.070(3) 0.037(3) 0.045(2) 0.005(2) 0.010(2) 0.001(2) C2 0.055(3) 0.036(3) 0.060(4) 0.005(3) 0.021(3) -0.004(3) C4 0.067(3) 0.053(4) 0.040(3) -0.002(3) 0.011(2) -0.004(3) C6 0.071(4) 0.062(4) 0.035(3) -0.004(3) -0.001(3) -0.006(3) C7 0.068(4) 0.064(4) 0.055(3) -0.005(4) 0.005(3) 0.004(3) C8 0.070(4) 0.067(4) 0.056(3) -0.006(3) 0.004(3) 0.005(3) C9 0.083(5) 0.094(6) 0.077(4) -0.016(5) 0.015(4) 0.006(4) C10 0.068(5) 0.114(7) 0.100(5) 0.014(5) 0.013(4) 0.008(6) C11 0.066(4) 0.115(7) 0.082(4) 0.021(5) 0.005(4) -0.004(5) C12 0.078(5) 0.091(5) 0.076(4) 0.022(4) 0.003(3) 0.009(4) C13 0.067(4) 0.073(4) 0.053(3) -0.007(4) 0.005(3) 0.002(3) C14 0.092(5) 0.075(5) 0.074(4) 0.000(4) 0.001(4) 0.031(4) C15 0.078(4) 0.068(5) 0.060(3) 0.001(4) 0.004(3) -0.001(4) C17 0.066(3) 0.039(3) 0.053(3) -0.001(3) 0.015(2) -0.008(3) C18 0.097(4) 0.039(3) 0.086(4) 0.001(4) 0.035(3) 0.010(3) C19 0.073(4) 0.037(3) 0.045(3) -0.001(3) 0.016(3) 0.001(3) C20 0.068(4) 0.061(4) 0.055(3) 0.005(3) 0.001(3) -0.013(3) C21 0.070(4) 0.072(4) 0.072(4) 0.004(4) 0.006(3) 0.005(4) C22 0.091(5) 0.044(3) 0.064(4) 0.008(3) 0.036(3) 0.003(3) C23 0.090(4) 0.046(4) 0.048(3) 0.000(4) 0.017(3) -0.001(3) C24 0.071(3) 0.048(3) 0.045(3) -0.010(3) 0.009(3) -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 1.231(7) . . yes O3 C2 1.274(9) . . yes O5 C4 1.434(6) . . yes N16 C17 1.492(8) . . yes C2 C4 1.522(8) . . yes C4 C6 1.508(9) . . yes C6 C7 1.362(9) . . yes C6 C15 1.418(11) . . yes C7 C8 1.458(10) . . yes C8 C9 1.399(10) . . yes C8 C13 1.406(11) . . yes C9 C10 1.344(12) . . yes C10 C11 1.418(15) . . yes C11 C12 1.322(11) . . yes C12 C13 1.452(11) . . yes C13 C14 1.380(10) . . yes C14 C15 1.367(11) . . yes C17 C18 1.546(10) . . yes C17 C19 1.525(9) . . yes C19 C20 1.362(9) . . yes C19 C24 1.387(8) . . yes C20 C21 1.417(10) . . yes C21 C22 1.386(10) . . yes C22 C23 1.369(10) . . yes C22 C25 1.494(11) . . yes C23 C24 1.424(9) . . yes C25 C26 1.515(16) . . yes O5 H5 0.96(8) . . yes N16 H16A 0.960(5) . . yes N16 H16B 0.960(6) . . yes N16 H16C 0.960(4) . . yes C4 H4 1.08(9) . . yes C7 H7 1.080(8) . . yes C9 H9 1.080(9) . . yes C10 H10 1.081(8) . . yes C11 H11 1.080(8) . . yes C12 H12 1.080(9) . . yes C14 H14 1.080(8) . . yes C15 H15 1.080(7) . . yes C17 H17 1.080(5) . . yes C18 H18A 1.080(7) . . yes C18 H18B 1.080(7) . . yes C18 H18C 1.080(7) . . yes C20 H20 1.080(6) . . yes C21 H21 1.079(6) . . yes C23 H23 1.079(6) . . yes C24 H24 1.081(6) . . yes C25 H25A 1.079(8) . . yes C25 H25B 1.080(7) . . yes C26 H26A 1.079(12) . . yes C26 H26B 1.081(12) . . yes C26 H26C 1.080(10) . . 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 123.4(5) . . . yes O1 C2 C4 120.3(6) . . . yes O3 C2 C4 116.1(6) . . . yes O5 C4 C2 111.3(5) . . . yes O5 C4 C6 109.3(5) . . . yes C2 C4 C6 109.8(5) . . . yes C4 C6 C7 121.9(6) . . . yes C4 C6 C15 119.7(6) . . . yes C7 C6 C15 118.1(6) . . . yes C6 C7 C8 121.0(7) . . . yes C7 C8 C9 121.2(7) . . . yes C7 C8 C13 118.2(6) . . . yes C9 C8 C13 120.5(7) . . . yes C8 C9 C10 120.3(8) . . . yes C9 C10 C11 120.1(8) . . . yes C10 C11 C12 121.7(8) . . . yes C11 C12 C13 119.8(8) . . . yes C8 C13 C12 117.5(6) . . . yes C8 C13 C14 119.7(7) . . . yes C12 C13 C14 122.7(8) . . . yes C13 C14 C15 121.0(8) . . . yes C6 C15 C14 121.9(6) . . . yes N16 C17 C18 108.0(5) . . . yes N16 C17 C19 113.4(6) . . . yes C18 C17 C19 111.3(5) . . . yes C17 C19 C20 117.2(6) . . . yes C17 C19 C24 121.9(5) . . . yes C20 C19 C24 120.5(6) . . . yes C19 C20 C21 120.0(6) . . . yes C20 C21 C22 120.4(6) . . . yes C21 C22 C23 119.3(6) . . . yes C21 C22 C25 120.6(6) . . . yes C23 C22 C25 120.2(6) . . . yes C22 C23 C24 120.7(6) . . . yes C19 C24 C23 119.1(5) . . . yes C22 C25 C26 116.1(7) . . . yes C4 O5 H5 102.5(46) . . . yes C17 N16 H16A 113.0(5) . . . yes C17 N16 H16B 109.1(5) . . . yes C17 N16 H16C 108.7(4) . . . yes H16A N16 H16B 108.6(4) . . . yes H16A N16 H16C 108.5(5) . . . yes H16B N16 H16C 109.0(6) . . . yes O5 C4 H4 109.8(37) . . . yes C2 C4 H4 109.4(37) . . . yes C6 C4 H4 107.2(36) . . . yes C6 C7 H7 119.8(7) . . . yes C8 C7 H7 119.1(6) . . . yes C8 C9 H9 118.8(7) . . . yes C10 C9 H9 120.9(8) . . . yes C9 C10 H10 119.9(10) . . . yes C11 C10 H10 120.0(8) . . . yes C10 C11 H11 118.3(7) . . . yes C12 C11 H11 120.0(9) . . . yes C11 C12 H12 120.4(8) . . . yes C13 C12 H12 119.7(7) . . . yes C13 C14 H14 119.3(7) . . . yes C15 C14 H14 119.6(7) . . . yes C6 C15 H15 118.9(7) . . . yes C14 C15 H15 119.2(8) . . . yes N16 C17 H17 108.8(5) . . . yes C18 C17 H17 107.6(6) . . . yes C19 C17 H17 107.6(5) . . . yes C17 C18 H18A 107.4(6) . . . yes C17 C18 H18B 109.3(6) . . . yes C17 C18 H18C 110.5(6) . . . yes H18A C18 H18B 110.3(7) . . . yes H18A C18 H18C 110.3(6) . . . yes H18B C18 H18C 109.0(6) . . . yes C19 C20 H20 120.1(6) . . . yes C21 C20 H20 119.9(6) . . . yes C20 C21 H21 120.1(7) . . . yes C22 C21 H21 119.5(7) . . . yes C22 C23 H23 120.0(6) . . . yes C24 C23 H23 119.3(6) . . . yes C19 C24 H24 120.6(6) . . . yes C23 C24 H24 120.3(6) . . . yes C22 C25 H25A 107.1(8) . . . yes C22 C25 H25B 109.9(7) . . . yes C26 C25 H25A 105.7(7) . . . yes C26 C25 H25B 108.8(9) . . . yes H25A C25 H25B 108.9(7) . . . yes C25 C26 H26A 116.8(9) . . . yes C25 C26 H26B 105.6(9) . . . yes C25 C26 H26C 108.8(11) . . . yes H26A C26 H26B 108.2(12) . . . yes H26A C26 H26C 108.3(10) . . . yes H26B C26 H26C 108.9(9) . . . yes #===END data_sngarpcl _chemical_name_systematic ; (R)-p-Chlorophenylethylammnonium (S)-2-Naphthylglycolate ; _chemical_name_common (S)-2/(R)-3k _chemical_compound_source 'Saigo laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.05 _chemical_formula_moiety 'C20 H20 N1 O3 Cl1 ' _chemical_formula_weight 357.80 _chemical_melting_point 176.5-182.0 deg _cell_length_a 8.611(1) _cell_length_b 31.413(4) _cell_length_c 6.754(1) _cell_angle_alpha 90.000000(0) _cell_angle_beta 90.000000(0) _cell_angle_gamma 90.000000(0) _cell_volume 1826.9(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 1.300 _diffrn_radiation_type 'Cu K-alpha' _diffrn_radiation_wavelength 1.54178 _exptl_absorpt_coefficient_mu 20.00 _cell_measurement_temperature '293' _diffrn_measurement_device 'Mac Science MXC18' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 1871 _reflns_number_total 1743 _reflns_number_observed 1532 _reflns_observed_criterion 'refl_observed_if_I_>_2.50_sigma(I)' _diffrn_reflns_av_R_equivalents 0.081 _diffrn_reflns_theta_max 51.50 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.101 _refine_ls_wR_factor_obs 0.133 _refine_ls_hydrogen_treatment 'noref' _refine_ls_number_reflns 1532 _refine_ls_number_parameters 226 _refine_ls_goodness_of_fit_obs 1.576 _refine_ls_weighting_scheme 'Count statistics' _refine_ls_shift/esd_max 0.4696 _refine_ls_shift/esd_mean 0.1032 _refine_diff_density_min -0.40 _refine_diff_density_max 0.65 _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 0.05606 _diffrn_orient_matrix_UB_12 -0.02408 _diffrn_orient_matrix_UB_13 0.06528 _diffrn_orient_matrix_UB_21 0.09623 _diffrn_orient_matrix_UB_22 0.01774 _diffrn_orient_matrix_UB_23 0.00737 _diffrn_orient_matrix_UB_31 -0.03293 _diffrn_orient_matrix_UB_32 0.01091 _diffrn_orient_matrix_UB_33 0.13268 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X+0.5,-Y,+Z+0.5 +X+0.5,-Y+0.5,-Z -X,+Y+0.5,-Z+0.5 _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting 'Orthorhombic' #================================================== # 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 Cl1 -1.4971(4) -0.3034(1) -1.5982(5) 0.116(2) 1.000 Uij O2 -0.9838(5) -0.4966(1) -0.7562(8) 0.060(2) 1.000 Uij O3 -1.0824(5) -0.4834(2) -0.4585(7) 0.065(3) 1.000 Uij O4 -0.6951(5) -0.4823(2) -0.5694(8) 0.076(3) 1.000 Uij N5 -1.1649(6) -0.4645(2) -1.0712(7) 0.053(3) 1.000 Uij C6 -1.3724(7) -0.4060(2) -1.2897(9) 0.055(3) 1.000 Uij C7 -0.9761(6) -0.4812(2) -0.5861(9) 0.048(3) 1.000 Uij C8 -0.8286(7) -0.4560(2) -0.5301(9) 0.054(3) 1.000 Uij C9 -1.1783(7) -0.4185(2) -1.0165(9) 0.053(3) 1.000 Uij C10 -1.2537(7) -0.3909(2) -1.1739(10) 0.055(3) 1.000 Uij C11 -0.8210(7) -0.4166(2) -0.6594(13) 0.071(4) 1.000 Uij C12 -1.4465(8) -0.3788(2) -1.4254(10) 0.062(3) 1.000 Uij C13 -1.2832(10) -0.3212(2) -1.3164(15) 0.080(5) 1.000 Uij C14 -0.7383(10) -0.4190(3) -0.8386(14) 0.085(5) 1.000 Uij C15 -1.2104(8) -0.3498(2) -1.1816(14) 0.079(4) 1.000 Uij C16 -1.2660(10) -0.4143(3) -0.8182(12) 0.080(5) 1.000 Uij C17 -1.4006(9) -0.3374(2) -1.4295(12) 0.074(4) 1.000 Uij C18 -0.7296(13) -0.3874(4) -0.9800(21) 0.113(8) 1.000 Uij C19 -0.7988(10) -0.3525(3) -0.9213(16) 0.092(5) 1.000 Uij C20 -0.8865(9) -0.3417(2) -0.7588(14) 0.079(4) 1.000 Uij C21 -0.9600(19) -0.3063(6) -0.7292(41) 0.21(2) 1.000 Uij C22 -0.8940(11) -0.3809(3) -0.6029(27) 0.130(7) 1.000 Uij C23 -0.943(3) -0.275(0) -0.874(5) 0.20(2) 1.000 Uij C24 -0.854(2) -0.279(1) -1.042(3) 0.14(1) 1.000 Uij C25 -0.7849(16) -0.3150(4) -1.0923(27) 0.138(9) 1.000 Uij H4 -0.603(13) -0.467(3) -0.533(17) 0.08(7) 1.000 Uiso H5A -1.118(17) -0.482(4) -0.971(22) 0.053 1.000 Uiso H5B -1.267(17) -0.475(4) -1.098(22) 0.053 1.000 Uiso H5C -1.10361 -0.46650 -1.18959 0.053 1.000 Uiso H6 -1.40639 -0.43898 -1.27937 0.055 1.000 Uiso H8 -0.84171 -0.44363 -0.38198 0.054 1.000 Uiso H9 -1.06312 -0.40646 -0.98640 0.053 1.000 Uiso H12 -1.54017 -0.38978 -1.51844 0.062 1.000 Uiso H13 -1.24500 -0.28865 -1.33132 0.080 1.000 Uiso H14 -0.67969 -0.44850 -0.87280 0.086 1.000 Uiso H15 -1.12278 -0.33834 -1.08034 0.079 1.000 Uiso H16A -1.27478 -0.38121 -0.77587 0.080 1.000 Uiso H16B -1.38118 -0.42751 -0.83447 0.080 1.000 Uiso H16C -1.20488 -0.43171 -0.70427 0.080 1.000 Uiso H18 -0.66544 -0.39124 -1.11623 0.113 1.000 Uiso H21 -1.02667 -0.30066 -0.59622 0.211 1.000 Uiso H22 -0.95826 -0.37719 -0.46672 0.131 1.000 Uiso H23 -1.002(5) -0.245(1) -0.853(6) 0.204 1.000 Uiso H24 -0.845(5) -0.252(1) -1.136(6) 0.141 1.000 Uiso H25 -0.72635 -0.31994 -1.23192 0.138 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 Cl1 0.127(2) 0.108(2) 0.113(2) 0.012(1) -0.024(2) 0.051(2) O2 0.060(2) 0.058(2) 0.063(3) 0.001(2) -0.004(2) -0.017(2) O3 0.055(2) 0.086(3) 0.055(2) -0.009(2) 0.002(2) 0.004(2) O4 0.045(2) 0.104(4) 0.078(3) 0.013(2) -0.002(2) 0.019(3) N5 0.058(3) 0.060(3) 0.041(2) 0.000(2) 0.001(2) 0.002(2) C6 0.052(3) 0.064(3) 0.049(3) -0.002(2) 0.001(3) -0.004(3) C7 0.043(3) 0.046(3) 0.054(3) 0.004(2) 0.000(2) 0.010(3) C8 0.048(3) 0.061(3) 0.052(3) 0.007(2) -0.004(3) -0.006(3) C9 0.052(3) 0.067(3) 0.040(3) -0.001(3) -0.005(2) -0.003(2) C10 0.046(3) 0.062(3) 0.056(3) 0.001(3) -0.006(3) 0.003(3) C11 0.051(3) 0.060(3) 0.101(6) -0.011(3) -0.031(4) 0.014(4) C12 0.059(3) 0.072(4) 0.056(3) 0.002(3) -0.005(3) -0.004(3) C13 0.086(5) 0.062(4) 0.093(6) -0.003(3) -0.002(5) 0.013(4) C14 0.090(5) 0.091(5) 0.076(5) -0.026(5) -0.003(5) 0.025(4) C15 0.065(4) 0.072(4) 0.100(6) -0.013(3) -0.022(4) -0.004(4) C16 0.083(5) 0.096(5) 0.060(4) 0.022(4) -0.002(4) -0.010(4) C17 0.073(4) 0.067(4) 0.083(5) 0.012(3) 0.006(4) 0.021(4) C18 0.099(6) 0.127(8) 0.114(8) 0.000(6) 0.034(7) 0.004(7) C19 0.069(4) 0.085(5) 0.121(8) -0.011(4) -0.004(5) -0.032(6) C20 0.067(4) 0.075(4) 0.096(6) 0.003(3) -0.012(4) -0.032(4) C21 0.12(1) 0.16(1) 0.36(3) 0.02(1) -0.07(2) -0.16(2) C22 0.076(5) 0.067(5) 0.248(18)-0.010(4) -0.051(9) -0.027(8) C23 0.20(2) 0.06(1) 0.35(3) -0.05(1) -0.15(2) 0.05(1) C24 0.12(1) 0.13(1) 0.17(2) -0.03(1) -0.01(1) 0.06(1) C25 0.118(8) 0.086(6) 0.210(16)-0.024(6) -0.047(10) 0.059(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 Cl1 C17 1.770(9) . . yes O2 C7 1.248(8) . . yes O3 C7 1.260(8) . . yes O4 C8 1.439(8) . . yes N5 C9 1.497(8) . . yes C6 C10 1.371(9) . . yes C6 C12 1.407(10) . . yes C7 C8 1.543(9) . . yes C8 C11 1.518(10) . . yes C9 C10 1.518(9) . . yes C9 C16 1.543(11) . . yes C10 C15 1.344(10) . . yes C11 C14 1.406(13) . . yes C11 C22 1.341(12) . . yes C12 C17 1.357(10) . . yes C13 C15 1.425(12) . . yes C13 C17 1.365(12) . . yes C14 C18 1.380(16) . . yes C18 C19 1.309(16) . . yes C19 C20 1.374(14) . . yes C19 C25 1.654(19) . . yes C20 C21 1.30(2) . . yes C20 C22 1.621(16) . . yes C21 C23 1.39(4) . . yes C23 C24 1.38(4) . . yes C24 C25 1.31(3) . . yes O4 H4 0.96(12) . . yes N5 H5A 0.96(15) . . yes N5 H5B 0.96(15) . . yes N5 H5C 0.960(5) . . yes C6 H6 1.080(6) . . yes C8 H8 1.079(7) . . yes C9 H9 1.081(7) . . yes C12 H12 1.079(7) . . yes C13 H13 1.081(8) . . yes C14 H14 1.080(9) . . yes C15 H15 1.080(9) . . yes C16 H16A 1.081(8) . . yes C16 H16B 1.081(9) . . yes C16 H16C 1.081(9) . . yes C18 H18 1.080(14) . . yes C21 H21 1.08(3) . . yes C22 H22 1.080(17) . . yes C23 H23 1.08(5) . . yes C24 H24 1.08(5) . . yes C25 H25 1.080(18) . . 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 C10 C6 C12 120.0(6) . . . yes O2 C7 O3 124.7(6) . . . yes O2 C7 C8 117.9(6) . . . yes O3 C7 C8 117.3(6) . . . yes O4 C8 C7 108.5(5) . . . yes O4 C8 C11 109.1(6) . . . yes C7 C8 C11 108.3(6) . . . yes N5 C9 C10 114.3(5) . . . yes N5 C9 C16 109.4(6) . . . yes C10 C9 C16 110.6(6) . . . yes C6 C10 C9 121.4(6) . . . yes C6 C10 C15 121.1(7) . . . yes C9 C10 C15 117.2(7) . . . yes C8 C11 C14 118.4(6) . . . yes C8 C11 C22 119.9(10) . . . yes C14 C11 C22 121.7(10) . . . yes C6 C12 C17 117.6(7) . . . yes C15 C13 C17 116.6(7) . . . yes C11 C14 C18 125.9(9) . . . yes C10 C15 C13 120.5(8) . . . yes Cl1 C17 C12 117.0(6) . . . yes Cl1 C17 C13 118.9(6) . . . yes C12 C17 C13 124.1(8) . . . yes C14 C18 C19 111.6(12) . . . yes C18 C19 C20 134.1(11) . . . yes C18 C19 C25 110.6(11) . . . yes C20 C19 C25 115.1(9) . . . yes C19 C20 C21 126.9(14) . . . yes C19 C20 C22 110.8(8) . . . yes C21 C20 C22 122.2(14) . . . yes C20 C21 C23 116.5(21) . . . yes C11 C22 C20 115.6(13) . . . yes C21 C23 C24 124.6(16) . . . yes C23 C24 C25 123.2(17) . . . yes C19 C25 C24 113.3(15) . . . yes C8 O4 H4 109.3(64) . . . yes C9 N5 H5A 114.2(82) . . . yes C9 N5 H5B 108.1(79) . . . yes C9 N5 H5C 108.0(5) . . . yes H5A N5 H5B 108.8(119) . . . yes H5A N5 H5C 108.7(88) . . . yes H5B N5 H5C 109.0(90) . . . yes C10 C6 H6 119.8(6) . . . yes C12 C6 H6 120.2(6) . . . yes O4 C8 H8 117.4(6) . . . yes C7 C8 H8 109.0(6) . . . yes C11 C8 H8 104.2(6) . . . yes N5 C9 H9 108.2(6) . . . yes C10 C9 H9 109.0(6) . . . yes C16 C9 H9 104.9(6) . . . yes C6 C12 H12 121.6(7) . . . yes C17 C12 H12 120.8(7) . . . yes C15 C13 H13 121.6(8) . . . yes C17 C13 H13 121.8(8) . . . yes C11 C14 H14 117.7(8) . . . yes C18 C14 H14 116.4(10) . . . yes C10 C15 H15 119.3(8) . . . yes C13 C15 H15 120.1(7) . . . yes C9 C16 H16A 110.1(7) . . . yes C9 C16 H16B 109.2(7) . . . yes C9 C16 H16C 109.7(7) . . . yes H16A C16 H16B 109.4(8) . . . yes H16A C16 H16C 109.5(7) . . . yes H16B C16 H16C 109.0(7) . . . yes C14 C18 H18 122.6(11) . . . yes C19 C18 H18 125.6(12) . . . yes C20 C21 H21 121.7(20) . . . yes C23 C21 H21 121.7(17) . . . yes C11 C22 H22 124.9(12) . . . yes C20 C22 H22 119.5(8) . . . yes C21 C23 H23 118.2(33) . . . yes C24 C23 H23 117.2(30) . . . yes C23 C24 H24 116.3(26) . . . yes C25 C24 H24 120.4(28) . . . yes C19 C25 H25 122.9(10) . . . yes C24 C25 H25 123.8(16) . . . yes #===END