# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Stephen Loeb' _publ_contact_author_address ; Dept of Chemistry & Biochemistry University of Windsor Windsor Ontario N9B 3P4 CANADA ; _publ_contact_author_phone '+ 519 253-3000 ext 3529' _publ_contact_author_fax '+ 519 973-7098 ' _publ_contact_author_email loeb@uwindsor.ca _publ_section_title ; Branched [n]rotaxanes (n = 2-4) from multiple dibenzo-24-crown- 8 ether wheels and 1,2-bis(4,4\^AA-dipyridinium)ethane axles ; loop_ _publ_author_name 'Stephen Loeb' 'David A. Tramontozzi' data_3-Phenoxymethyl-dibenzo-24-crown-8ether _database_code_depnum_ccdc_archive 'CCDC 258420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H38 O9' _chemical_formula_weight 554.61 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.5216(13) _cell_length_b 8.6643(13) _cell_length_c 10.4987(16) _cell_angle_alpha 92.857(3) _cell_angle_beta 96.328(3) _cell_angle_gamma 113.673(3) _cell_volume 701.82(18) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 3131 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 23.26 _reflns_number_total 2474 _reflns_number_gt 2248 _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^)+(0.1106P)^2^+0.7500P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(4) _refine_ls_number_reflns 2474 _refine_ls_number_parameters 361 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0965 _refine_ls_wR_factor_ref 0.2429 _refine_ls_wR_factor_gt 0.2346 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.150 _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 -0.2242(8) 0.4881(8) 0.2441(6) 0.0543(16) Uani 1 1 d . . . O2 O -0.0639(11) 0.2824(9) 0.3621(8) 0.082(2) Uani 1 1 d . . . O3 O 0.2157(12) 0.2565(12) 0.5421(9) 0.102(3) Uani 1 1 d . . . O4 O 0.5554(8) 0.5323(8) 0.6542(7) 0.0650(19) Uani 1 1 d . . . O5 O 0.6925(9) 0.7695(8) 0.5105(8) 0.075(2) Uani 1 1 d . . . O6 O 0.5245(13) 0.9683(13) 0.3831(10) 0.107(3) Uani 1 1 d . . . O7 O 0.2507(13) 1.0018(10) 0.2077(10) 0.094(3) Uani 1 1 d . . . O8 O -0.0931(10) 0.7250(10) 0.0997(7) 0.080(2) Uani 1 1 d . . . O9 O 1.3697(10) 0.9552(10) 0.8165(7) 0.081(2) Uani 1 1 d . . . C1 C -0.2690(13) 0.6501(14) 0.0839(10) 0.065(3) Uani 1 1 d . . . C2 C -0.3692(14) 0.7044(13) 0.0054(11) 0.068(3) Uani 1 1 d . . . H2A H -0.3196 0.8000 -0.0375 0.082 Uiso 1 1 calc R . . C3 C -0.553(2) 0.6112(19) -0.0101(14) 0.111(5) Uani 1 1 d . . . H3A H -0.6224 0.6350 -0.0737 0.133 Uiso 1 1 calc R . . C4 C -0.6247(17) 0.4919(15) 0.0648(14) 0.089(4) Uani 1 1 d . . . H4A H -0.7442 0.4435 0.0625 0.107 Uiso 1 1 calc R . . C5 C -0.5177(12) 0.4368(12) 0.1499(11) 0.070(3) Uani 1 1 d . . . H5A H -0.5687 0.3446 0.1957 0.084 Uiso 1 1 calc R . . C6 C -0.3458(14) 0.5173(12) 0.1633(9) 0.061(3) Uani 1 1 d . . . C7 C -0.2949(15) 0.3740(14) 0.3339(11) 0.067(3) Uani 1 1 d . . . H7A H -0.3640 0.2615 0.2903 0.081 Uiso 1 1 calc R . . H7B H -0.3683 0.4097 0.3810 0.081 Uiso 1 1 calc R . . C8 C -0.1455(15) 0.3724(16) 0.4248(11) 0.075(3) Uani 1 1 d . . . H8A H -0.0627 0.4877 0.4525 0.090 Uiso 1 1 calc R . . H8B H -0.1876 0.3188 0.5005 0.090 Uiso 1 1 calc R . . C9 C 0.0969(18) 0.3459(19) 0.3593(15) 0.107(5) Uani 1 1 d . . . H9A H 0.1238 0.4581 0.3323 0.128 Uiso 1 1 calc R . . H9B H 0.1143 0.2807 0.2887 0.128 Uiso 1 1 calc R . . C10 C 0.227(2) 0.366(4) 0.4585(17) 0.212(14) Uani 1 1 d . . . H10A H 0.3291 0.3818 0.4185 0.254 Uiso 1 1 calc R . . H10B H 0.2525 0.4732 0.5081 0.254 Uiso 1 1 calc R . . C11 C 0.2850(18) 0.3168(16) 0.6721(12) 0.089(4) Uani 1 1 d . . . H11A H 0.2298 0.2277 0.7254 0.107 Uiso 1 1 calc R . . H11B H 0.2562 0.4110 0.6956 0.107 Uiso 1 1 calc R . . C12 C 0.4743(11) 0.3731(13) 0.7013(10) 0.062(3) Uani 1 1 d . . . H12A H 0.5085 0.3829 0.7936 0.075 Uiso 1 1 calc R . . H12B H 0.5091 0.2912 0.6607 0.075 Uiso 1 1 calc R . . C13 C 0.7308(14) 0.6027(11) 0.6684(8) 0.058(3) Uani 1 1 d U . . C14 C 0.8490(18) 0.5687(16) 0.7549(11) 0.081(3) Uani 1 1 d . . . H14A H 0.8048 0.4933 0.8152 0.097 Uiso 1 1 calc R . . C15 C 1.0138(12) 0.6351(13) 0.7559(8) 0.059(3) Uani 1 1 d . . . H15A H 1.0832 0.5925 0.8035 0.070 Uiso 1 1 calc R . . C16 C 1.0880(11) 0.7720(13) 0.6847(7) 0.051(2) Uani 1 1 d . . . C17 C 0.9851(14) 0.8193(12) 0.6044(9) 0.057(3) Uani 1 1 d . . . H17A H 1.0319 0.9074 0.5540 0.068 Uiso 1 1 calc R . . C18 C 0.8035(12) 0.7315(11) 0.5986(10) 0.059(3) Uani 1 1 d . . . C19 C 0.7559(16) 0.8849(13) 0.4145(10) 0.067(3) Uani 1 1 d . . . H19A H 0.8279 0.8500 0.3651 0.081 Uiso 1 1 calc R . . H19B H 0.8251 0.9985 0.4561 0.081 Uiso 1 1 calc R . . C20 C 0.6055(18) 0.8830(13) 0.3284(12) 0.084(4) Uani 1 1 d . . . H20A H 0.6442 0.9325 0.2506 0.101 Uiso 1 1 calc R . . H20B H 0.5237 0.7665 0.3038 0.101 Uiso 1 1 calc R . . C21 C 0.344(3) 0.876(3) 0.378(2) 0.155(9) Uani 1 1 d . . . H21A H 0.3266 0.7685 0.4109 0.186 Uiso 1 1 calc R . . H21B H 0.3060 0.9367 0.4393 0.186 Uiso 1 1 calc R . . C22 C 0.245(2) 0.8441(14) 0.280(2) 0.111(6) Uani 1 1 d . . . H22A H 0.1284 0.7839 0.3001 0.133 Uiso 1 1 calc R . . H22B H 0.2683 0.7680 0.2222 0.133 Uiso 1 1 calc R . . C23 C 0.1820(16) 0.9509(14) 0.0759(12) 0.074(3) Uani 1 1 d . . . H23A H 0.2180 0.8642 0.0457 0.089 Uiso 1 1 calc R . . H23B H 0.2320 1.0472 0.0275 0.089 Uiso 1 1 calc R . . C24 C -0.018(2) 0.8812(15) 0.0455(14) 0.093(4) Uani 1 1 d . . . H24A H -0.0572 0.9623 0.0814 0.112 Uiso 1 1 calc R . . H24B H -0.0527 0.8638 -0.0470 0.112 Uiso 1 1 calc R . . C25 C 1.2889(16) 0.8563(14) 0.6931(10) 0.080(3) Uani 1 1 d . . . H25A H 1.3316 0.7691 0.6809 0.096 Uiso 1 1 calc R . . H25B H 1.3203 0.9293 0.6246 0.096 Uiso 1 1 calc R . . C26 C 1.5484(10) 1.0415(11) 0.8451(8) 0.042(2) Uani 1 1 d U . . C27 C 1.6185(18) 1.1275(14) 0.9636(11) 0.078(4) Uani 1 1 d . . . H27A H 1.5425 1.1230 1.0219 0.094 Uiso 1 1 calc R . . C28 C 1.7934(18) 1.2215(15) 1.0052(14) 0.093(5) Uani 1 1 d . . . H28A H 1.8392 1.2802 1.0866 0.111 Uiso 1 1 calc R . . C29 C 1.891(2) 1.2161(15) 0.9088(16) 0.119(6) Uani 1 1 d . . . H29A H 2.0088 1.2861 0.9257 0.143 Uiso 1 1 calc R . . C30 C 1.8348(13) 1.1192(14) 0.7909(12) 0.074(3) Uani 1 1 d . . . H30A H 1.9087 1.1129 0.7339 0.089 Uiso 1 1 calc R . . C31 C 1.6503(14) 1.0296(12) 0.7656(9) 0.067(3) Uani 1 1 d . . . H31A H 1.6013 0.9599 0.6888 0.080 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 0.044(4) 0.057(4) 0.063(4) 0.030(3) 0.008(3) 0.020(3) O2 0.080(6) 0.061(5) 0.105(6) 0.003(4) 0.016(5) 0.030(5) O3 0.084(7) 0.106(7) 0.104(7) 0.020(6) -0.019(5) 0.035(6) O4 0.036(3) 0.048(4) 0.116(6) 0.039(4) 0.017(4) 0.017(3) O5 0.059(5) 0.048(4) 0.117(6) 0.025(4) 0.021(4) 0.016(4) O6 0.088(7) 0.121(7) 0.141(8) 0.024(6) -0.010(6) 0.077(6) O7 0.094(7) 0.076(5) 0.115(7) 0.011(5) 0.032(6) 0.031(5) O8 0.068(5) 0.079(6) 0.079(5) 0.011(4) 0.009(4) 0.016(5) O9 0.065(5) 0.104(5) 0.074(4) 0.002(4) 0.009(4) 0.036(4) C1 0.046(6) 0.079(7) 0.081(7) -0.010(6) -0.016(5) 0.043(6) C2 0.051(6) 0.062(6) 0.087(7) 0.031(6) 0.003(6) 0.019(5) C3 0.117(13) 0.085(10) 0.101(10) -0.024(9) 0.008(9) 0.017(9) C4 0.061(8) 0.051(6) 0.133(11) -0.012(7) 0.000(8) 0.004(6) C5 0.030(5) 0.045(5) 0.105(8) -0.011(6) -0.002(6) -0.008(5) C6 0.053(6) 0.056(6) 0.051(5) 0.020(5) 0.008(5) -0.004(5) C7 0.066(7) 0.068(6) 0.087(7) 0.009(6) 0.036(6) 0.041(6) C8 0.057(7) 0.092(8) 0.068(6) 0.027(6) -0.002(5) 0.023(7) C9 0.076(10) 0.097(10) 0.123(11) 0.039(8) 0.043(9) 0.000(8) C10 0.059(9) 0.33(3) 0.131(13) 0.157(18) -0.014(9) -0.041(14) C11 0.090(9) 0.079(8) 0.086(8) 0.039(7) 0.045(8) 0.008(7) C12 0.028(5) 0.066(6) 0.066(6) 0.032(5) -0.010(4) -0.007(4) C13 0.071(6) 0.033(4) 0.056(5) 0.029(4) 0.024(5) 0.001(4) C14 0.087(10) 0.093(8) 0.062(6) 0.016(6) 0.006(6) 0.036(8) C15 0.038(5) 0.090(7) 0.055(5) 0.040(5) -0.008(4) 0.034(6) C16 0.040(5) 0.096(7) 0.030(4) -0.003(5) -0.003(4) 0.046(5) C17 0.078(8) 0.053(5) 0.053(5) 0.018(4) 0.021(5) 0.037(6) C18 0.052(6) 0.046(5) 0.097(7) -0.018(5) -0.003(5) 0.044(5) C19 0.080(8) 0.052(6) 0.062(6) 0.020(5) -0.007(5) 0.022(5) C20 0.120(11) 0.046(6) 0.102(9) -0.004(6) 0.007(8) 0.053(7) C21 0.110(15) 0.110(13) 0.26(3) 0.084(16) -0.010(16) 0.057(12) C22 0.066(9) 0.038(6) 0.212(19) 0.013(9) 0.016(10) 0.005(6) C23 0.071(8) 0.053(6) 0.093(8) 0.017(6) 0.007(7) 0.021(6) C24 0.118(12) 0.078(8) 0.116(9) 0.032(7) 0.063(9) 0.059(8) C25 0.098(9) 0.084(7) 0.058(6) 0.001(5) -0.003(6) 0.043(7) C26 0.023(4) 0.065(5) 0.055(5) 0.009(4) 0.019(3) 0.031(4) C27 0.103(10) 0.076(7) 0.087(8) 0.020(6) 0.073(8) 0.052(8) C28 0.093(10) 0.089(8) 0.136(11) 0.039(8) 0.099(9) 0.055(8) C29 0.142(14) 0.051(7) 0.139(12) -0.025(8) -0.065(11) 0.038(8) C30 0.033(5) 0.071(7) 0.101(8) 0.000(6) -0.007(5) 0.010(5) C31 0.072(7) 0.055(6) 0.047(5) -0.032(4) -0.037(5) 0.015(5) _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 C6 1.377(12) . ? O1 C7 1.403(12) . ? O2 C9 1.259(15) . ? O2 C8 1.419(14) . ? O3 C10 1.31(2) . ? O3 C11 1.410(15) . ? O4 C13 1.356(12) . ? O4 C12 1.415(11) . ? O5 C18 1.395(12) . ? O5 C19 1.447(12) . ? O6 C20 1.344(14) . ? O6 C21 1.42(2) . ? O7 C23 1.416(15) . ? O7 C22 1.585(18) . ? O8 C1 1.360(13) . ? O8 C24 1.424(14) . ? O9 C26 1.389(11) . ? O9 C25 1.451(12) . ? C1 C2 1.355(14) . ? C1 C6 1.435(15) . ? C2 C3 1.429(19) . ? C3 C4 1.319(19) . ? C4 C5 1.439(17) . ? C5 C6 1.333(14) . ? C7 C8 1.510(15) . ? C9 C10 1.385(19) . ? C11 C12 1.476(16) . ? C13 C18 1.339(13) . ? C13 C14 1.411(15) . ? C14 C15 1.285(16) . ? C15 C16 1.398(13) . ? C16 C17 1.344(12) . ? C16 C25 1.558(15) . ? C17 C18 1.416(14) . ? C19 C20 1.478(15) . ? C21 C22 1.19(2) . ? C23 C24 1.548(18) . ? C26 C31 1.298(13) . ? C26 C27 1.359(15) . ? C27 C28 1.386(19) . ? C28 C29 1.39(2) . ? C29 C30 1.382(18) . ? C30 C31 1.433(15) . ? 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 C6 O1 C7 113.8(7) . . ? C9 O2 C8 121.7(11) . . ? C10 O3 C11 118.7(14) . . ? C13 O4 C12 117.3(7) . . ? C18 O5 C19 122.1(8) . . ? C20 O6 C21 114.7(14) . . ? C23 O7 C22 110.6(9) . . ? C1 O8 C24 116.2(10) . . ? C26 O9 C25 121.3(8) . . ? O8 C1 C2 122.7(11) . . ? O8 C1 C6 116.5(9) . . ? C2 C1 C6 120.6(10) . . ? C1 C2 C3 118.4(12) . . ? C4 C3 C2 120.8(16) . . ? C3 C4 C5 119.8(14) . . ? C6 C5 C4 120.3(11) . . ? C5 C6 O1 128.4(9) . . ? C5 C6 C1 119.0(10) . . ? O1 C6 C1 112.6(8) . . ? O1 C7 C8 107.2(9) . . ? O2 C8 C7 109.8(9) . . ? O2 C9 C10 127.6(14) . . ? O3 C10 C9 124.0(15) . . ? O3 C11 C12 114.7(10) . . ? O4 C12 C11 108.5(8) . . ? C18 C13 O4 116.2(9) . . ? C18 C13 C14 114.8(10) . . ? O4 C13 C14 128.8(8) . . ? C15 C14 C13 124.2(11) . . ? C14 C15 C16 119.5(9) . . ? C17 C16 C15 119.5(9) . . ? C17 C16 C25 121.8(9) . . ? C15 C16 C25 118.5(8) . . ? C16 C17 C18 118.3(9) . . ? C13 C18 O5 117.1(9) . . ? C13 C18 C17 122.7(9) . . ? O5 C18 C17 120.0(9) . . ? O5 C19 C20 108.4(10) . . ? O6 C20 C19 113.0(10) . . ? C22 C21 O6 122(2) . . ? C21 C22 O7 115.9(13) . . ? O7 C23 C24 115.2(10) . . ? O8 C24 C23 109.3(11) . . ? O9 C25 C16 111.4(8) . . ? C31 C26 C27 119.1(8) . . ? C31 C26 O9 121.4(8) . . ? C27 C26 O9 119.2(8) . . ? C26 C27 C28 125.7(9) . . ? C27 C28 C29 110.8(14) . . ? C30 C29 C28 127.8(16) . . ? C29 C30 C31 112.9(13) . . ? C26 C31 C30 122.9(9) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.419 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.060