# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Toda, F.' 'Kuroda, Reiko' 'Senzaki, Mami' _publ_requested_journal 'Chemical Communications' _publ_contact_author_name 'Prof F Toda' _publ_contact_author_address ; Department of Chemistry, Faculty of Science Okayama University of Science Ridaicho Okayama 700-0005 JAPAN ; _publ_contact_author_email 'TODA@CHEM.OUS.AC.JP' _publ_section_title ; A new supramolecular system consisted of three polar and one non-polar components: Inclusion complex of (+)- and (-)-bis-B-naphthol, benzoquinone and aromatic hydrocarbon which shows high molecular recognition ability ; data_1 _database_code_CSD 176714 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Complex of bi-2-naphthol, p-benzoquinone and toluene ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 O2, 0.5(C6 H4 O2), C7H8' _chemical_formula_sum 'C30 H24 O3' _chemical_formula_weight 432.49 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1524(9) _cell_length_b 10.8140(10) _cell_length_c 11.7724(11) _cell_angle_alpha 98.011(2) _cell_angle_beta 97.747(2) _cell_angle_gamma 115.541(2) _cell_volume 1126.98(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4925 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 28.28 _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 7120 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4925 _reflns_number_gt 2727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4925 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41917(15) 0.93162(16) 0.14781(13) 0.0408(4) Uani 1 1 d . . . H1A H 0.3872 0.9813 0.1200 0.061 Uiso 1 1 calc R . . O2 O 0.53076(19) 0.68226(17) 0.04921(13) 0.0486(4) Uani 1 1 d . . . H2A H 0.5889 0.7630 0.0479 0.073 Uiso 1 1 calc R . . C1 C 0.5716(2) 0.9999(2) 0.17484(17) 0.0303(5) Uani 1 1 d . . . C2 C 0.6500(2) 1.1331(2) 0.14957(19) 0.0364(5) Uani 1 1 d . . . H2B H 0.5977 1.1752 0.1142 0.044 Uiso 1 1 calc R . . C3 C 0.8013(3) 1.1997(2) 0.1768(2) 0.0425(6) Uani 1 1 d . . . H3A H 0.8520 1.2871 0.1593 0.051 Uiso 1 1 calc R . . C4 C 0.8838(2) 1.1385(2) 0.2314(2) 0.0414(6) Uani 1 1 d . . . C5 C 1.0412(3) 1.2068(3) 0.2616(3) 0.0638(8) Uani 1 1 d . . . H5A H 1.0934 1.2937 0.2435 0.077 Uiso 1 1 calc R . . C6 C 1.1181(3) 1.1476(3) 0.3167(3) 0.0725(10) Uani 1 1 d . . . H6A H 1.2221 1.1937 0.3354 0.087 Uiso 1 1 calc R . . C7 C 1.0412(3) 1.0177(3) 0.3455(3) 0.0578(8) Uani 1 1 d . . . H7A H 1.0946 0.9789 0.3846 0.069 Uiso 1 1 calc R . . C8 C 0.8890(2) 0.9476(2) 0.3168(2) 0.0413(6) Uani 1 1 d . . . H8A H 0.8397 0.8606 0.3355 0.050 Uiso 1 1 calc R . . C9 C 0.8048(2) 1.0053(2) 0.25879(19) 0.0327(5) Uani 1 1 d . . . C10 C 0.6453(2) 0.9346(2) 0.22765(17) 0.0279(4) Uani 1 1 d . . . C11 C 0.5106(2) 0.6757(2) 0.16064(19) 0.0352(5) Uani 1 1 d . . . C12 C 0.4346(3) 0.5386(2) 0.1794(2) 0.0459(6) Uani 1 1 d . . . H12A H 0.4028 0.4613 0.1178 0.055 Uiso 1 1 calc R . . C13 C 0.4079(3) 0.5194(3) 0.2865(2) 0.0464(6) Uani 1 1 d . . . H13A H 0.3580 0.4286 0.2978 0.056 Uiso 1 1 calc R . . C14 C 0.4545(2) 0.6347(3) 0.3814(2) 0.0388(5) Uani 1 1 d . . . C15 C 0.4232(3) 0.6167(3) 0.4932(2) 0.0541(7) Uani 1 1 d . . . H15A H 0.3715 0.5266 0.5054 0.065 Uiso 1 1 calc R . . C16 C 0.4677(3) 0.7292(4) 0.5828(2) 0.0612(8) Uani 1 1 d . . . H16A H 0.4454 0.7158 0.6555 0.073 Uiso 1 1 calc R . . C17 C 0.5470(3) 0.8655(3) 0.5664(2) 0.0532(7) Uani 1 1 d . . . H17A H 0.5778 0.9422 0.6285 0.064 Uiso 1 1 calc R . . C18 C 0.5794(3) 0.8865(3) 0.45946(19) 0.0402(5) Uani 1 1 d . . . H18A H 0.6330 0.9777 0.4499 0.048 Uiso 1 1 calc R . . C19 C 0.5328(2) 0.7726(2) 0.36365(18) 0.0316(5) Uani 1 1 d . . . C20 C 0.5609(2) 0.7917(2) 0.25011(18) 0.0284(4) Uani 1 1 d . . . C31 C 0.9237(6) 0.5728(4) 0.1093(4) 0.0918(12) Uani 1 1 d . . . H31A H 0.9017 0.5499 0.0276 0.110 Uiso 1 1 calc R . . C32 C 0.8113(4) 0.5471(3) 0.1658(4) 0.0777(10) Uani 1 1 d . . . H32A H 0.7123 0.5071 0.1250 0.093 Uiso 1 1 calc R . . C33 C 0.8507(4) 0.5842(3) 0.2922(3) 0.0748(10) Uani 1 1 d . . . H33A H 0.7771 0.5682 0.3356 0.090 Uiso 1 1 calc R . . C34 C 1.0010(4) 0.6446(3) 0.3486(3) 0.0717(9) Uani 1 1 d . . . C35 C 1.1030(5) 0.6654(4) 0.2831(6) 0.1012(14) Uani 1 1 d . . . H35A H 1.2033 0.7061 0.3208 0.121 Uiso 1 1 calc R . . C36 C 1.0679(7) 0.6309(5) 0.1679(6) 0.1186(19) Uani 1 1 d . . . H36A H 1.1430 0.6466 0.1261 0.142 Uiso 1 1 calc R . . C37 C 1.0470(8) 0.6880(5) 0.4777(4) 0.176(3) Uani 1 1 d . . . H37A H 1.1538 0.7276 0.5010 0.263 Uiso 1 1 calc R . . H37B H 1.0011 0.6078 0.5111 0.263 Uiso 1 1 calc R . . H37C H 1.0160 0.7570 0.5050 0.263 Uiso 1 1 calc R . . C42 C 0.1574(3) 1.0490(3) 0.0267(2) 0.0449(6) Uani 1 1 d . . . C43 C 0.0555(3) 0.9212(3) 0.0595(2) 0.0519(7) Uani 1 1 d . . . H43A H 0.0948 0.8715 0.0987 0.062 Uiso 1 1 calc R . . C44 C -0.0910(3) 0.8751(3) 0.0347(2) 0.0519(7) Uani 1 1 d . . . H44A H -0.1529 0.7936 0.0563 0.062 Uiso 1 1 calc R . . O4 O 0.29326(17) 1.09042(18) 0.04863(15) 0.0471(4) Uani 1 1 d . . . 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 O1 0.0292(8) 0.0495(10) 0.0485(9) 0.0208(8) 0.0065(7) 0.0199(7) O2 0.0593(11) 0.0355(10) 0.0361(9) 0.0049(7) 0.0107(8) 0.0092(8) C1 0.0304(10) 0.0345(12) 0.0263(10) 0.0073(9) 0.0058(8) 0.0152(9) C2 0.0430(12) 0.0372(13) 0.0386(12) 0.0149(10) 0.0077(10) 0.0253(10) C3 0.0402(13) 0.0296(13) 0.0550(15) 0.0188(11) 0.0070(11) 0.0117(10) C4 0.0340(12) 0.0308(13) 0.0529(14) 0.0161(11) 0.0015(10) 0.0094(10) C5 0.0364(13) 0.0418(16) 0.102(2) 0.0367(15) 0.0036(14) 0.0056(11) C6 0.0291(13) 0.0542(18) 0.120(3) 0.0414(18) -0.0042(14) 0.0056(12) C7 0.0332(12) 0.0496(17) 0.086(2) 0.0315(15) -0.0055(13) 0.0149(11) C8 0.0343(12) 0.0355(13) 0.0511(14) 0.0186(11) 0.0031(10) 0.0125(10) C9 0.0306(11) 0.0268(12) 0.0367(12) 0.0082(9) 0.0023(9) 0.0107(9) C10 0.0283(10) 0.0273(11) 0.0254(10) 0.0058(8) 0.0037(8) 0.0109(9) C11 0.0337(11) 0.0317(13) 0.0357(12) 0.0086(10) 0.0066(9) 0.0108(9) C12 0.0426(13) 0.0285(13) 0.0524(15) 0.0058(11) 0.0045(11) 0.0060(10) C13 0.0377(13) 0.0334(14) 0.0636(17) 0.0233(12) 0.0133(11) 0.0079(10) C14 0.0310(11) 0.0439(14) 0.0487(14) 0.0235(12) 0.0144(10) 0.0179(10) C15 0.0559(16) 0.0684(19) 0.0628(17) 0.0420(16) 0.0334(13) 0.0367(14) C16 0.078(2) 0.095(2) 0.0507(16) 0.0450(17) 0.0375(15) 0.0612(19) C17 0.0753(18) 0.075(2) 0.0361(13) 0.0191(13) 0.0183(12) 0.0544(16) C18 0.0512(14) 0.0462(15) 0.0353(13) 0.0146(11) 0.0104(10) 0.0314(12) C19 0.0284(10) 0.0381(13) 0.0364(12) 0.0149(10) 0.0098(9) 0.0196(9) C20 0.0243(10) 0.0286(12) 0.0326(11) 0.0104(9) 0.0063(8) 0.0114(8) C31 0.149(4) 0.082(3) 0.090(3) 0.043(2) 0.049(3) 0.081(3) C32 0.084(2) 0.0475(19) 0.100(3) 0.0133(18) -0.002(2) 0.0361(17) C33 0.081(2) 0.0469(18) 0.115(3) 0.0305(19) 0.047(2) 0.0345(17) C34 0.087(2) 0.0457(18) 0.079(2) 0.0101(16) -0.0050(19) 0.0346(17) C35 0.076(3) 0.073(3) 0.177(5) 0.048(3) 0.038(3) 0.045(2) C36 0.129(4) 0.093(3) 0.198(6) 0.084(4) 0.098(5) 0.076(3) C37 0.302(8) 0.102(4) 0.095(4) -0.014(3) -0.063(4) 0.108(5) C42 0.0398(13) 0.0566(16) 0.0568(15) 0.0317(13) 0.0194(11) 0.0306(12) C43 0.0435(13) 0.0621(17) 0.0748(18) 0.0472(15) 0.0232(12) 0.0341(13) C44 0.0432(13) 0.0598(17) 0.0738(18) 0.0456(14) 0.0258(12) 0.0298(12) O4 0.0346(9) 0.0590(12) 0.0594(11) 0.0298(9) 0.0163(7) 0.0254(8) _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 O1 C1 1.363(2) . ? O2 C11 1.362(3) . ? C1 C10 1.377(3) . ? C1 C2 1.411(3) . ? C2 C3 1.352(3) . ? C3 C4 1.415(3) . ? C4 C5 1.408(3) . ? C4 C9 1.424(3) . ? C5 C6 1.360(4) . ? C6 C7 1.398(4) . ? C7 C8 1.362(3) . ? C8 C9 1.417(3) . ? C9 C10 1.427(3) . ? C10 C20 1.492(3) . ? C11 C20 1.370(3) . ? C11 C12 1.412(3) . ? C12 C13 1.350(3) . ? C13 C14 1.410(3) . ? C14 C15 1.415(3) . ? C14 C19 1.418(3) . ? C15 C16 1.355(4) . ? C16 C17 1.398(4) . ? C17 C18 1.368(3) . ? C18 C19 1.408(3) . ? C19 C20 1.428(3) . ? C31 C32 1.343(5) . ? C31 C36 1.352(6) . ? C32 C33 1.439(5) . ? C33 C34 1.393(4) . ? C34 C35 1.334(6) . ? C34 C37 1.473(5) . ? C35 C36 1.311(6) . ? C42 O4 1.228(3) . ? C42 C43 1.467(3) . ? C42 C44 1.471(3) 2_575 ? C43 C44 1.323(3) . ? C44 C42 1.471(3) 2_575 ? 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 O1 C1 C10 117.67(18) . . ? O1 C1 C2 120.71(17) . . ? C10 C1 C2 121.61(18) . . ? C3 C2 C1 120.08(18) . . ? C2 C3 C4 121.1(2) . . ? C5 C4 C3 122.0(2) . . ? C5 C4 C9 119.14(19) . . ? C3 C4 C9 118.84(19) . . ? C6 C5 C4 121.0(2) . . ? C5 C6 C7 120.2(2) . . ? C8 C7 C6 120.7(2) . . ? C7 C8 C9 120.9(2) . . ? C8 C9 C4 118.12(19) . . ? C8 C9 C10 122.30(19) . . ? C4 C9 C10 119.58(18) . . ? C1 C10 C9 118.70(18) . . ? C1 C10 C20 120.97(17) . . ? C9 C10 C20 120.32(16) . . ? O2 C11 C20 123.70(19) . . ? O2 C11 C12 115.0(2) . . ? C20 C11 C12 121.3(2) . . ? C13 C12 C11 120.2(2) . . ? C12 C13 C14 121.1(2) . . ? C13 C14 C15 121.9(2) . . ? C13 C14 C19 118.9(2) . . ? C15 C14 C19 119.1(2) . . ? C16 C15 C14 120.8(3) . . ? C15 C16 C17 120.4(2) . . ? C18 C17 C16 120.3(3) . . ? C17 C18 C19 121.1(2) . . ? C18 C19 C14 118.3(2) . . ? C18 C19 C20 122.3(2) . . ? C14 C19 C20 119.5(2) . . ? C11 C20 C19 118.98(19) . . ? C11 C20 C10 119.59(18) . . ? C19 C20 C10 121.42(19) . . ? C32 C31 C36 121.9(4) . . ? C31 C32 C33 117.1(4) . . ? C34 C33 C32 118.9(3) . . ? C35 C34 C33 118.7(4) . . ? C35 C34 C37 120.5(5) . . ? C33 C34 C37 120.8(4) . . ? C36 C35 C34 122.8(4) . . ? C35 C36 C31 120.7(5) . . ? O4 C42 C43 121.3(2) . . ? O4 C42 C44 121.1(2) . 2_575 ? C43 C42 C44 117.6(2) . 2_575 ? C44 C43 C42 121.5(2) . . ? C43 C44 C42 120.9(2) . 2_575 ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.383 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.049 #---END data_2 _database_code_CSD 176715 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Complex of racemic bi-2-naphthol, p-benzoquinone and stilbene ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 O2, 0.5(C6 H4 O2), 0.5(C14 H12)' _chemical_formula_sum 'C30 H22 O3' _chemical_formula_weight 430.48 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1828(14) _cell_length_b 10.8554(14) _cell_length_c 11.5925(16) _cell_angle_alpha 99.418(3) _cell_angle_beta 98.393(3) _cell_angle_gamma 116.126(3) _cell_volume 1100.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3724 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 24.71 _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 6125 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3724 _reflns_number_gt 2560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1193P)^2^+0.9901P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3724 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2052 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 O1 O -0.0273(3) 0.8185(2) 0.4572(2) 0.0265(6) Uani 1 1 d . . . H1A H -0.0862 0.7365 0.4551 0.040 Uiso 1 1 calc R . . O2 O 0.0861(3) 0.5769(3) 0.3568(2) 0.0249(6) Uani 1 1 d . . . H2A H 0.1197 0.5288 0.3846 0.037 Uiso 1 1 calc R . . O3 O 0.2054(3) 0.4145(3) 0.4525(2) 0.0254(6) Uani 1 1 d . . . C1 C -0.0078(4) 0.8272(4) 0.3435(3) 0.0203(8) Uani 1 1 d . . . C2 C 0.0658(4) 0.9652(4) 0.3287(3) 0.0239(8) Uani 1 1 d . . . H2B H 0.0960 1.0429 0.3934 0.029 Uiso 1 1 calc R . . C3 C 0.0930(4) 0.9858(4) 0.2196(3) 0.0240(8) Uani 1 1 d . . . H3A H 0.1420 1.0777 0.2109 0.029 Uiso 1 1 calc R . . C4 C 0.0480(4) 0.8693(4) 0.1194(3) 0.0224(8) Uani 1 1 d . . . C5 C 0.0809(4) 0.8871(4) 0.0073(3) 0.0258(8) Uani 1 1 d . . . H5A H 0.1335 0.9783 -0.0021 0.031 Uiso 1 1 calc R . . C6 C 0.0372(4) 0.7736(4) -0.0874(3) 0.0286(9) Uani 1 1 d . . . H6A H 0.0609 0.7878 -0.1603 0.034 Uiso 1 1 calc R . . C7 C -0.0439(4) 0.6342(4) -0.0751(3) 0.0261(8) Uani 1 1 d . . . H7A H -0.0745 0.5568 -0.1401 0.031 Uiso 1 1 calc R . . C8 C -0.0776(4) 0.6131(4) 0.0328(3) 0.0213(8) Uani 1 1 d . . . H8A H -0.1321 0.5210 0.0397 0.026 Uiso 1 1 calc R . . C9 C -0.0310(4) 0.7290(4) 0.1340(3) 0.0201(8) Uani 1 1 d . . . C10 C -0.0599(3) 0.7084(3) 0.2490(3) 0.0172(7) Uani 1 1 d . . . C11 C -0.1443(4) 0.5636(3) 0.2680(3) 0.0189(7) Uani 1 1 d . . . C12 C -0.3056(4) 0.4877(3) 0.2320(3) 0.0183(7) Uani 1 1 d . . . C13 C -0.3918(4) 0.5426(4) 0.1740(3) 0.0211(8) Uani 1 1 d . . . H13A H -0.3424 0.6302 0.1570 0.025 Uiso 1 1 calc R . . C14 C -0.5459(4) 0.4701(4) 0.1425(3) 0.0242(8) Uani 1 1 d . . . H14A H -0.6000 0.5092 0.1053 0.029 Uiso 1 1 calc R . . C15 C -0.6235(4) 0.3365(4) 0.1660(3) 0.0269(9) Uani 1 1 d . . . H15A H -0.7284 0.2873 0.1440 0.032 Uiso 1 1 calc R . . C16 C -0.5439(4) 0.2795(4) 0.2211(3) 0.0246(8) Uani 1 1 d . . . H16A H -0.5958 0.1911 0.2362 0.029 Uiso 1 1 calc R . . C17 C -0.3850(4) 0.3516(4) 0.2556(3) 0.0220(8) Uani 1 1 d . . . C18 C -0.2994(4) 0.2953(4) 0.3130(3) 0.0234(8) Uani 1 1 d . . . H18A H -0.3493 0.2068 0.3283 0.028 Uiso 1 1 calc R . . C19 C -0.1459(4) 0.3676(4) 0.3461(3) 0.0229(8) Uani 1 1 d . . . H19A H -0.0922 0.3284 0.3835 0.027 Uiso 1 1 calc R . . C20 C -0.0681(4) 0.5023(4) 0.3238(3) 0.0194(8) Uani 1 1 d . . . C21 C 0.3416(4) 0.4534(4) 0.4741(3) 0.0220(8) Uani 1 1 d . . . C22 C 0.4059(4) 0.3749(4) 0.5327(3) 0.0234(8) Uani 1 1 d . . . H22A H 0.3421 0.2940 0.5537 0.028 Uiso 1 1 calc R . . C23 C 0.5528(4) 0.4171(4) 0.5563(3) 0.0239(8) Uani 1 1 d . . . H23A H 0.5901 0.3647 0.5924 0.029 Uiso 1 1 calc R . . C31 C 0.3965(5) 0.8583(4) 0.2616(4) 0.0328(9) Uani 1 1 d . . . H31A H 0.3082 0.8444 0.2845 0.039 Uiso 1 1 calc R . . C32 C 0.3901(5) 0.8100(4) 0.1425(4) 0.0406(11) Uani 1 1 d . . . H32A H 0.2979 0.7647 0.0856 0.049 Uiso 1 1 calc R . . C33 C 0.5200(5) 0.8285(5) 0.1067(4) 0.0401(11) Uani 1 1 d . . . H33A H 0.5156 0.7973 0.0259 0.048 Uiso 1 1 calc R . . C34 C 0.6551(5) 0.8931(4) 0.1912(4) 0.0343(10) Uani 1 1 d . . . H34A H 0.7423 0.9037 0.1678 0.041 Uiso 1 1 calc R . . C35 C 0.6630(4) 0.9424(4) 0.3106(4) 0.0306(9) Uani 1 1 d . . . H35A H 0.7555 0.9861 0.3669 0.037 Uiso 1 1 calc R . . C36 C 0.5336(4) 0.9278(4) 0.3485(3) 0.0281(9) Uani 1 1 d . . . C37 C 0.5516(4) 0.9919(4) 0.4762(4) 0.0335(9) Uani 1 1 d . . . H37A H 0.6452 1.0242 0.5283 0.040 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 O1 0.0355(14) 0.0163(13) 0.0258(15) 0.0087(10) 0.0124(11) 0.0081(11) O2 0.0250(13) 0.0248(14) 0.0307(15) 0.0165(11) 0.0082(11) 0.0133(11) O3 0.0238(13) 0.0274(14) 0.0326(15) 0.0176(11) 0.0116(11) 0.0140(11) C1 0.0229(17) 0.0232(19) 0.0182(19) 0.0102(15) 0.0073(14) 0.0115(15) C2 0.0246(18) 0.0175(18) 0.031(2) 0.0068(15) 0.0090(16) 0.0099(15) C3 0.0228(18) 0.0144(18) 0.037(2) 0.0157(16) 0.0116(16) 0.0062(15) C4 0.0210(17) 0.026(2) 0.029(2) 0.0171(16) 0.0109(15) 0.0137(16) C5 0.0291(19) 0.024(2) 0.035(2) 0.0213(17) 0.0164(17) 0.0146(17) C6 0.033(2) 0.043(2) 0.026(2) 0.0233(18) 0.0190(17) 0.0242(19) C7 0.033(2) 0.035(2) 0.023(2) 0.0111(16) 0.0098(16) 0.0248(18) C8 0.0254(18) 0.0208(18) 0.024(2) 0.0120(15) 0.0078(15) 0.0141(15) C9 0.0181(16) 0.0248(19) 0.0247(19) 0.0141(15) 0.0068(14) 0.0132(15) C10 0.0165(16) 0.0189(18) 0.0220(19) 0.0120(14) 0.0071(14) 0.0106(14) C11 0.0267(18) 0.0165(18) 0.0194(18) 0.0099(14) 0.0116(15) 0.0118(15) C12 0.0246(18) 0.0156(17) 0.0173(18) 0.0077(14) 0.0095(14) 0.0092(15) C13 0.0256(18) 0.0160(18) 0.026(2) 0.0129(15) 0.0097(15) 0.0104(15) C14 0.0249(18) 0.026(2) 0.025(2) 0.0120(15) 0.0052(15) 0.0134(16) C15 0.0182(17) 0.024(2) 0.037(2) 0.0150(16) 0.0071(16) 0.0059(15) C16 0.0251(18) 0.0152(18) 0.031(2) 0.0114(15) 0.0092(16) 0.0049(15) C17 0.0293(19) 0.0166(18) 0.0234(19) 0.0099(14) 0.0121(15) 0.0105(15) C18 0.031(2) 0.0171(18) 0.028(2) 0.0150(15) 0.0126(16) 0.0114(16) C19 0.033(2) 0.0232(19) 0.023(2) 0.0144(15) 0.0107(16) 0.0182(17) C20 0.0221(17) 0.0208(18) 0.0184(18) 0.0067(14) 0.0076(14) 0.0115(15) C21 0.029(2) 0.0217(19) 0.0232(19) 0.0097(15) 0.0109(15) 0.0162(16) C22 0.0300(19) 0.0196(18) 0.030(2) 0.0188(15) 0.0165(16) 0.0128(15) C23 0.032(2) 0.0222(19) 0.029(2) 0.0175(16) 0.0135(16) 0.0170(16) C31 0.037(2) 0.029(2) 0.044(3) 0.0202(19) 0.0151(19) 0.0202(18) C32 0.049(3) 0.036(2) 0.041(3) 0.010(2) 0.001(2) 0.027(2) C33 0.066(3) 0.037(2) 0.033(2) 0.0161(19) 0.018(2) 0.034(2) C34 0.046(2) 0.026(2) 0.048(3) 0.0257(19) 0.026(2) 0.0222(19) C35 0.032(2) 0.0169(19) 0.045(3) 0.0165(17) 0.0057(18) 0.0114(16) C36 0.041(2) 0.0145(18) 0.035(2) 0.0172(16) 0.0138(18) 0.0137(17) C37 0.037(2) 0.025(2) 0.042(2) 0.0179(18) 0.0088(18) 0.0144(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.373(4) . ? O2 C20 1.368(4) . ? O3 C21 1.230(4) . ? C1 C10 1.383(5) . ? C1 C2 1.403(5) . ? C2 C3 1.366(5) . ? C3 C4 1.418(5) . ? C4 C5 1.411(5) . ? C4 C9 1.429(5) . ? C5 C6 1.361(5) . ? C6 C7 1.413(5) . ? C7 C8 1.373(5) . ? C8 C9 1.419(5) . ? C9 C10 1.437(5) . ? C10 C11 1.496(4) . ? C11 C20 1.383(5) . ? C11 C12 1.430(5) . ? C12 C13 1.413(5) . ? C12 C17 1.434(4) . ? C13 C14 1.367(5) . ? C14 C15 1.409(5) . ? C15 C16 1.367(5) . ? C16 C17 1.409(5) . ? C17 C18 1.417(5) . ? C18 C19 1.361(5) . ? C19 C20 1.412(5) . ? C21 C22 1.472(5) . ? C21 C23 1.483(5) 2_666 ? C22 C23 1.326(5) . ? C23 C21 1.483(5) 2_666 ? C31 C32 1.376(6) . ? C31 C36 1.395(6) . ? C32 C33 1.384(6) . ? C33 C34 1.370(6) . ? C34 C35 1.377(6) . ? C35 C36 1.400(5) . ? C36 C37 1.477(6) . ? C37 C37 1.319(8) 2_676 ? 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 O1 C1 C10 122.5(3) . . ? O1 C1 C2 115.5(3) . . ? C10 C1 C2 122.0(3) . . ? C3 C2 C1 120.2(3) . . ? C2 C3 C4 121.2(3) . . ? C5 C4 C3 122.5(3) . . ? C5 C4 C9 119.1(3) . . ? C3 C4 C9 118.4(3) . . ? C6 C5 C4 121.4(3) . . ? C5 C6 C7 120.1(3) . . ? C8 C7 C6 120.0(3) . . ? C7 C8 C9 121.4(3) . . ? C8 C9 C4 118.0(3) . . ? C8 C9 C10 122.0(3) . . ? C4 C9 C10 120.1(3) . . ? C1 C10 C9 118.1(3) . . ? C1 C10 C11 119.9(3) . . ? C9 C10 C11 121.9(3) . . ? C20 C11 C12 118.8(3) . . ? C20 C11 C10 120.6(3) . . ? C12 C11 C10 120.6(3) . . ? C13 C12 C11 122.3(3) . . ? C13 C12 C17 117.9(3) . . ? C11 C12 C17 119.8(3) . . ? C14 C13 C12 121.6(3) . . ? C13 C14 C15 120.4(3) . . ? C16 C15 C14 119.7(3) . . ? C15 C16 C17 121.4(3) . . ? C16 C17 C18 122.7(3) . . ? C16 C17 C12 119.0(3) . . ? C18 C17 C12 118.2(3) . . ? C19 C18 C17 121.6(3) . . ? C18 C19 C20 120.1(3) . . ? O2 C20 C11 117.5(3) . . ? O2 C20 C19 121.0(3) . . ? C11 C20 C19 121.5(3) . . ? O3 C21 C22 121.4(3) . . ? O3 C21 C23 120.9(3) . 2_666 ? C22 C21 C23 117.7(3) . 2_666 ? C23 C22 C21 121.4(3) . . ? C22 C23 C21 120.9(3) . 2_666 ? C32 C31 C36 120.9(4) . . ? C31 C32 C33 120.5(4) . . ? C34 C33 C32 119.5(4) . . ? C33 C34 C35 120.5(4) . . ? C34 C35 C36 121.0(4) . . ? C31 C36 C35 117.6(4) . . ? C31 C36 C37 124.1(3) . . ? C35 C36 C37 118.2(3) . . ? C37 C37 C36 126.6(5) 2_676 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.511 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.084 #--END