# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Lianxun Gao' _publ_contact_author_address ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; _publ_contact_author_email lxgao@ciac.jl.cn _publ_contact_author_phone +86-431-85262352 _publ_contact_author_fax +86-431-85262926 loop_ _publ_author_name _publ_author_address 'Chuanqing Kang' ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; 'Yabing He' ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; 'Zheng Bian' ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; 'Fushe Han' ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; 'Xuepeng Qiu' ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; ; Lianxun Gao ; ;Changchun Institute of Applied Chemistry, Chinese Academy of Sciences 5625 Renmin Street Changchun 130022 China ; _publ_section_title ; An organogel formed from a cyclic b-aminoalcohol ; # Attachment '- CCPub.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 823631' #TrackingRef '- CCPub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ((1S,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol ; _chemical_name_common ;((1S,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin- 3-yl)methanol ; _chemical_melting_point 110 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 N O' _chemical_formula_weight 163.21 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6435(14) _cell_length_b 6.500(1) _cell_length_c 14.390(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.698(2) _cell_angle_gamma 90.00 _cell_volume 864.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3025 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 26.17 _exptl_crystal_description 'transparent block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4797 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.21 _reflns_number_total 1863 _reflns_number_gt 1682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0411P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(14) _refine_ls_number_reflns 1863 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4235(2) 0.2075(4) 0.36257(14) 0.0323(5) Uani 1 1 d . . . H1A H 0.5140 0.2528 0.4073 0.039 Uiso 1 1 calc R . . H1B H 0.3489 0.3055 0.3654 0.039 Uiso 1 1 calc R . . C2 C 0.4382(2) 0.2019(3) 0.26117(13) 0.0264(4) Uani 1 1 d . . . C3 C 0.5166(2) 0.3535(4) 0.23184(15) 0.0325(5) Uani 1 1 d . . . H3 H 0.5538 0.4628 0.2732 0.039 Uiso 1 1 calc R . . C4 C 0.5405(2) 0.3449(4) 0.14221(15) 0.0363(5) Uani 1 1 d . . . H4 H 0.5941 0.4471 0.1232 0.044 Uiso 1 1 calc R . . C5 C 0.4843(2) 0.1836(4) 0.08064(15) 0.0396(6) Uani 1 1 d . . . H5 H 0.5014 0.1753 0.0204 0.048 Uiso 1 1 calc R . . C6 C 0.4034(2) 0.0358(4) 0.10849(15) 0.0350(5) Uani 1 1 d . . . H6 H 0.3644 -0.0711 0.0661 0.042 Uiso 1 1 calc R . . C7 C 0.3783(2) 0.0421(4) 0.19872(14) 0.0283(5) Uani 1 1 d . . . C8 C 0.2902(2) -0.1225(4) 0.22819(15) 0.0320(5) Uani 1 1 d . . . H8A H 0.3436 -0.2510 0.2371 0.038 Uiso 1 1 calc R . . H8B H 0.2009 -0.1423 0.1767 0.038 Uiso 1 1 calc R . . C9 C 0.2547(2) -0.0686(3) 0.32108(15) 0.0288(4) Uani 1 1 d . . . H9 H 0.1830 0.0425 0.3073 0.035 Uiso 1 1 calc R . . C10 C 0.1927(2) -0.2495(4) 0.36053(17) 0.0372(5) Uani 1 1 d . . . H10A H 0.1102 -0.3022 0.3104 0.045 Uiso 1 1 calc R . . H10B H 0.2649 -0.3576 0.3774 0.045 Uiso 1 1 calc R . . C11 C 0.0834(2) 0.7209(4) 0.66884(15) 0.0326(5) Uani 1 1 d . . . H11A H -0.0108 0.7862 0.6468 0.039 Uiso 1 1 calc R . . H11B H 0.1562 0.8233 0.6681 0.039 Uiso 1 1 calc R . . C12 C 0.1072(2) 0.6436(4) 0.77059(16) 0.0324(5) Uani 1 1 d . . . C13 C 0.0676(2) 0.7662(4) 0.83768(17) 0.0449(6) Uani 1 1 d . . . H13 H 0.0237 0.8928 0.8186 0.054 Uiso 1 1 calc R . . C14 C 0.0925(3) 0.7020(5) 0.93232(18) 0.0540(8) Uani 1 1 d . . . H14 H 0.0672 0.7862 0.9771 0.065 Uiso 1 1 calc R . . C15 C 0.1549(2) 0.5134(5) 0.96036(17) 0.0513(7) Uani 1 1 d . . . H15 H 0.1713 0.4688 1.0240 0.062 Uiso 1 1 calc R . . C16 C 0.1926(2) 0.3916(5) 0.89384(16) 0.0421(6) Uani 1 1 d . . . H16 H 0.2339 0.2634 0.9128 0.051 Uiso 1 1 calc R . . C17 C 0.1704(2) 0.4555(4) 0.79893(15) 0.0307(5) Uani 1 1 d . . . C18 C 0.2202(2) 0.3227(4) 0.72935(14) 0.0325(5) Uani 1 1 d . . . H18A H 0.1539 0.2080 0.7094 0.039 Uiso 1 1 calc R . . H18B H 0.3151 0.2673 0.7619 0.039 Uiso 1 1 calc R . . C19 C 0.2278(2) 0.4411(3) 0.64039(14) 0.0268(4) Uani 1 1 d . . . H19 H 0.3072 0.5409 0.6597 0.032 Uiso 1 1 calc R . . C20 C 0.2525(2) 0.3051(4) 0.56147(14) 0.0307(5) Uani 1 1 d . . . H20A H 0.1784 0.1995 0.5456 0.037 Uiso 1 1 calc R . . H20B H 0.2431 0.3871 0.5037 0.037 Uiso 1 1 calc R . . N1 N 0.38625(16) 0.0060(3) 0.39146(11) 0.0281(4) Uani 1 1 d . . . H1C H 0.3709 0.0150 0.4498 0.034 Uiso 1 1 d R . . N2 N 0.09115(16) 0.5533(3) 0.60271(11) 0.0278(4) Uani 1 1 d . . . H2B H 0.0871 0.6053 0.5446 0.033 Uiso 1 1 d R . . O1 O 0.14838(15) -0.1991(3) 0.44331(10) 0.0363(4) Uani 1 1 d . . . H1 H 0.0775 -0.1233 0.4274 0.054 Uiso 1 1 calc R . . O2 O 0.38989(14) 0.2106(2) 0.58875(10) 0.0311(4) Uani 1 1 d . . . H2 H 0.4529 0.2986 0.5953 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0381(11) 0.0316(12) 0.0322(11) -0.0050(10) 0.0180(9) -0.0006(10) C2 0.0265(9) 0.0271(11) 0.0272(10) 0.0004(9) 0.0103(8) 0.0052(9) C3 0.0339(11) 0.0293(12) 0.0351(11) 0.0023(10) 0.0112(9) 0.0011(9) C4 0.0351(11) 0.0383(14) 0.0375(12) 0.0103(11) 0.0134(9) 0.0001(10) C5 0.0380(12) 0.0557(17) 0.0284(11) 0.0061(11) 0.0150(9) 0.0020(12) C6 0.0321(11) 0.0440(14) 0.0288(11) -0.0052(11) 0.0087(8) -0.0027(11) C7 0.0243(10) 0.0320(12) 0.0291(10) 0.0021(10) 0.0086(7) 0.0030(9) C8 0.0311(11) 0.0323(13) 0.0336(11) -0.0048(10) 0.0108(9) -0.0035(9) C9 0.0241(9) 0.0291(11) 0.0346(11) 0.0026(9) 0.0108(8) 0.0025(9) C10 0.0370(11) 0.0333(13) 0.0474(12) 0.0030(11) 0.0221(10) 0.0037(10) C11 0.0296(10) 0.0262(12) 0.0424(12) 0.0004(10) 0.0111(9) 0.0031(9) C12 0.0220(10) 0.0378(13) 0.0376(12) -0.0070(10) 0.0089(8) -0.0018(9) C13 0.0371(12) 0.0480(16) 0.0513(14) -0.0161(12) 0.0152(10) 0.0025(11) C14 0.0442(14) 0.077(2) 0.0452(14) -0.0275(15) 0.0200(11) -0.0003(15) C15 0.0391(13) 0.083(2) 0.0353(12) -0.0037(14) 0.0156(10) -0.0011(15) C16 0.0383(12) 0.0569(17) 0.0331(12) 0.0034(11) 0.0134(9) 0.0025(12) C17 0.0232(10) 0.0376(13) 0.0311(11) -0.0033(9) 0.0075(8) -0.0016(9) C18 0.0346(11) 0.0336(13) 0.0301(11) 0.0019(10) 0.0108(8) 0.0071(10) C19 0.0237(9) 0.0276(11) 0.0295(10) -0.0008(9) 0.0085(8) -0.0009(9) C20 0.0263(10) 0.0356(13) 0.0310(10) -0.0026(10) 0.0095(8) -0.0012(9) N1 0.0306(9) 0.0305(10) 0.0261(8) 0.0004(8) 0.0130(7) 0.0015(8) N2 0.0282(9) 0.0285(10) 0.0274(9) 0.0027(8) 0.0089(7) 0.0016(8) O1 0.0343(8) 0.0379(10) 0.0427(8) 0.0123(7) 0.0209(6) 0.0083(7) O2 0.0285(7) 0.0314(8) 0.0357(8) -0.0005(7) 0.0130(6) 0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.450(3) . ? C1 C2 1.506(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.381(3) . ? C2 C7 1.386(3) . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 C6 1.368(3) . ? C5 H5 0.9300 . ? C6 C7 1.388(3) . ? C6 H6 0.9300 . ? C7 C8 1.501(3) . ? C8 C9 1.513(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.460(3) . ? C9 C10 1.503(3) . ? C9 H9 0.9800 . ? C10 O1 1.415(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.462(3) . ? C11 C12 1.502(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.375(3) . ? C12 C13 1.388(3) . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.374(5) . ? C14 H14 0.9300 . ? C15 C16 1.370(3) . ? C15 H15 0.9300 . ? C16 C17 1.384(3) . ? C16 H16 0.9300 . ? C17 C18 1.501(3) . ? C18 C19 1.514(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N2 1.467(2) . ? C19 C20 1.511(3) . ? C19 H19 0.9800 . ? C20 O2 1.410(2) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? N1 H1C 0.8953 . ? N2 H2B 0.8931 . ? O1 H1 0.8200 . ? O2 H2 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 110.83(17) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C7 119.96(17) . . ? C3 C2 C1 119.41(19) . . ? C7 C2 C1 120.58(18) . . ? C4 C3 C2 120.8(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.81(19) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 121.4(2) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C2 C7 C6 118.5(2) . . ? C2 C7 C8 120.99(17) . . ? C6 C7 C8 120.5(2) . . ? C7 C8 C9 111.99(17) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N1 C9 C10 111.01(17) . . ? N1 C9 C8 108.54(15) . . ? C10 C9 C8 111.60(19) . . ? N1 C9 H9 108.5 . . ? C10 C9 H9 108.5 . . ? C8 C9 H9 108.5 . . ? O1 C10 C9 112.72(19) . . ? O1 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? O1 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N2 C11 C12 111.28(19) . . ? N2 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N2 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C17 C12 C13 119.4(2) . . ? C17 C12 C11 121.17(19) . . ? C13 C12 C11 119.4(2) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 119.5(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C17 121.3(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 119.3(2) . . ? C12 C17 C18 120.84(19) . . ? C16 C17 C18 119.8(2) . . ? C17 C18 C19 112.00(18) . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N2 C19 C18 107.94(15) . . ? N2 C19 C20 109.37(15) . . ? C18 C19 C20 113.24(18) . . ? N2 C19 H19 108.7 . . ? C18 C19 H19 108.7 . . ? C20 C19 H19 108.7 . . ? O2 C20 C19 112.57(16) . . ? O2 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? O2 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C1 N1 C9 109.77(16) . . ? C1 N1 H1C 109.3 . . ? C9 N1 H1C 109.1 . . ? C11 N2 C19 109.76(15) . . ? C11 N2 H2B 109.3 . . ? C19 N2 H2B 109.1 . . ? C10 O1 H1 109.5 . . ? C20 O2 H2 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N2 0.82 1.94 2.754(2) 176.7 2_546 O2 H2 N1 0.82 2.02 2.842(2) 177.2 2_656 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.21 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.162 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.029