#------------------------------------------------------------------------------ #$Date: 2012-02-26 23:34:47 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35909 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/10/68/7106864.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7106864 loop_ _publ_author_name 'Chuanqing Kang' 'Yabing He' 'Zheng Bian' 'Fushe Han' 'Xuepeng Qiu' 'Lianxun Gao' _publ_section_title ; An organogel formed from a cyclic b-aminoalcohol ; _journal_name_full Chem.Commun. _journal_page_first 10746 _journal_volume 47 _journal_year 2011 _chemical_absolute_configuration unk _chemical_formula_sum 'C10 H13 N O' _chemical_formula_weight 163.21 _chemical_melting_point 110 _chemical_name_common ;((1S,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin- 3-yl)methanol ; _chemical_name_systematic ; ((1S,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 106.698(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.6435(14) _cell_length_b 6.500(1) _cell_length_c 14.390(2) _cell_measurement_reflns_used 3025 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 26.17 _cell_measurement_theta_min 2.96 _cell_volume 864.0(2) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 4797 _diffrn_reflns_theta_full 26.21 _diffrn_reflns_theta_max 26.21 _diffrn_reflns_theta_min 2.20 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'transparent block' _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.162 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.029 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(14) _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_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 1863 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0321 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0411P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.0820 _reflns_number_gt 1682 _reflns_number_total 1863 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c1cc13179f.txt _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M P2(1) _cod_database_code 7106864 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 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) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle 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_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance 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_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