# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Grepioni, Fabrizia' _publ_contact_author_email fabrizia.grepioni@unibo.it _publ_author_name 'Fabrizia Grepioni' data_2-oh-i _database_code_depnum_ccdc_archive 'CCDC 794773' #TrackingRef '- 2-OH-new.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CROWN ETHER COMPLEX' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Cs O11' _chemical_formula_weight 578.34 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.3337(3) _cell_length_b 14.6878(4) _cell_length_c 18.7462(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2294.60(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3105 _cell_measurement_theta_min 2.4395 _cell_measurement_theta_max 32.6505 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.082 _exptl_crystal_size_min 0.079 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.671 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.61590 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34 (release 24-02-2009 CrysAlis171 .NET) (compiled Feb 24 2009,11:20:51) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur S' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9238 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.1010 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 32.73 _reflns_number_total 6594 _reflns_number_gt 3738 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 68.00 101.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 26.3143 179.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 2 omega 16.00 99.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 26.3143 0.0000 90.0000 83 #__ type_ start__ end____ width___ exp.time_ 3 omega -46.00 -1.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - -26.7831 0.0000 30.0000 45 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0167P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.028(11) _refine_ls_number_reflns 6594 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0472 _refine_ls_wR_factor_gt 0.0426 _refine_ls_goodness_of_fit_ref 0.698 _refine_ls_restrained_S_all 0.698 _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 Cs1 Cs -0.15909(3) 0.593729(14) 0.945065(10) 0.04443(6) Uani 1 1 d . . . O1 O -0.2780(3) 0.80647(16) 0.99278(12) 0.0505(7) Uani 1 1 d . . . O2 O -0.2947(3) 0.75296(15) 0.84600(11) 0.0482(7) Uani 1 1 d . . . O3 O -0.4561(3) 0.5886(2) 0.81475(11) 0.0565(6) Uani 1 1 d . . . O4 O -0.4259(3) 0.45041(16) 0.91994(12) 0.0526(7) Uani 1 1 d . . . O5 O -0.3796(3) 0.50248(14) 1.06460(12) 0.0479(6) Uani 1 1 d . . . O6 O -0.2375(3) 0.66941(18) 1.09825(12) 0.0507(7) Uani 1 1 d . . . C1 C -0.2665(5) 0.7621(3) 1.11368(18) 0.0529(11) Uani 1 1 d . . . H1A H -0.2212 0.7774 1.1598 0.063 Uiso 1 1 calc R . . H1B H -0.3811 0.7733 1.1155 0.063 Uiso 1 1 calc R . . C2 C -0.1927(4) 0.8190(2) 1.0578(2) 0.0622(10) Uani 1 1 d . . . H2A H -0.1965 0.8825 1.0719 0.075 Uiso 1 1 calc R . . H2B H -0.0812 0.8019 1.0515 0.075 Uiso 1 1 calc R . . C3 C -0.2087(4) 0.8554(2) 0.9363(2) 0.0623(11) Uani 1 1 d . . . H3A H -0.0997 0.8343 0.9287 0.075 Uiso 1 1 calc R . . H3B H -0.2041 0.9195 0.9487 0.075 Uiso 1 1 calc R . . C4 C -0.3023(5) 0.8441(2) 0.86922(19) 0.0572(11) Uani 1 1 d . . . H4A H -0.4132 0.8611 0.8775 0.069 Uiso 1 1 calc R . . H4B H -0.2591 0.8839 0.8326 0.069 Uiso 1 1 calc R . . C5 C -0.3816(5) 0.7385(3) 0.78217(18) 0.0594(12) Uani 1 1 d . . . H5A H -0.3354 0.7750 0.7442 0.071 Uiso 1 1 calc R . . H5B H -0.4920 0.7577 0.7888 0.071 Uiso 1 1 calc R . . C6 C -0.3780(5) 0.6420(3) 0.76174(17) 0.0589(12) Uani 1 1 d . . . H6A H -0.4316 0.6339 0.7162 0.071 Uiso 1 1 calc R . . H6B H -0.2677 0.6220 0.7566 0.071 Uiso 1 1 calc R . . C7 C -0.4498(5) 0.4957(3) 0.79910(19) 0.0661(12) Uani 1 1 d . . . H7A H -0.3391 0.4771 0.7925 0.079 Uiso 1 1 calc R . . H7B H -0.5076 0.4836 0.7552 0.079 Uiso 1 1 calc R . . C8 C -0.5233(5) 0.4428(3) 0.8590(2) 0.0651(12) Uani 1 1 d . . . H8A H -0.6297 0.4661 0.8693 0.078 Uiso 1 1 calc R . . H8B H -0.5333 0.3793 0.8455 0.078 Uiso 1 1 calc R . . C9 C -0.4877(4) 0.4018(3) 0.97936(19) 0.0557(9) Uani 1 1 d . . . H9A H -0.4989 0.3379 0.9673 0.067 Uiso 1 1 calc R . . H9B H -0.5928 0.4253 0.9919 0.067 Uiso 1 1 calc R . . C10 C -0.3765(4) 0.4121(2) 1.04081(18) 0.0555(9) Uani 1 1 d . . . H10A H -0.4088 0.3717 1.0791 0.067 Uiso 1 1 calc R . . H10B H -0.2684 0.3958 1.0264 0.067 Uiso 1 1 calc R . . C11 C -0.2906(4) 0.5160(3) 1.12829(17) 0.0552(11) Uani 1 1 d . . . H11A H -0.1784 0.5017 1.1202 0.066 Uiso 1 1 calc R . . H11B H -0.3307 0.4762 1.1655 0.066 Uiso 1 1 calc R . . C12 C -0.3070(4) 0.6120(3) 1.15044(16) 0.0544(11) Uani 1 1 d . . . H12A H -0.4196 0.6270 1.1562 0.065 Uiso 1 1 calc R . . H12B H -0.2539 0.6211 1.1959 0.065 Uiso 1 1 calc R . . O7 O 0.0040(2) 0.41131(15) 0.90359(9) 0.0369(5) Uani 1 1 d . . . O8 O 0.0550(3) 0.41305(17) 0.78714(10) 0.0454(6) Uani 1 1 d . . . O9 O -0.4163(3) 0.04780(16) 0.92479(12) 0.0503(7) Uani 1 1 d . . . O10 O -0.3782(3) 0.17507(14) 0.98715(10) 0.0429(6) Uani 1 1 d . . . H10O H -0.4231 0.1461 1.0187 0.064 Uiso 1 1 calc R . . O11 O -0.0425(3) 0.09149(19) 0.71102(11) 0.0410(6) Uani 1 1 d . . . C13 C -0.2422(3) 0.1611(2) 0.87710(15) 0.0282(7) Uani 1 1 d . . . C14 C -0.1764(4) 0.24751(18) 0.88511(13) 0.0301(7) Uani 1 1 d . . . H14 H -0.2042 0.2829 0.9243 0.036 Uiso 1 1 calc R . . C15 C -0.0691(4) 0.2812(2) 0.83479(15) 0.0276(7) Uani 1 1 d . . . C16 C -0.0294(4) 0.2277(2) 0.77660(14) 0.0286(7) Uani 1 1 d . . . H16 H 0.0393 0.2507 0.7419 0.034 Uiso 1 1 calc R . . C17 C -0.0904(4) 0.1403(2) 0.76910(15) 0.0288(7) Uani 1 1 d . . . C18 C -0.1987(3) 0.1076(2) 0.81903(13) 0.0293(7) Uani 1 1 d . . . H18 H -0.2423 0.0497 0.8137 0.035 Uiso 1 1 calc R . . C19 C -0.3553(4) 0.12190(19) 0.93101(15) 0.0325(7) Uani 1 1 d . . . C20 C 0.0022(4) 0.37602(19) 0.84232(17) 0.0315(7) Uani 1 1 d . . . H11O H -0.066(5) 0.039(2) 0.7119(19) 0.066(14) Uiso 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 Cs1 0.05342(11) 0.03381(9) 0.04605(9) -0.00069(12) 0.01340(12) -0.00251(13) O1 0.0552(17) 0.0404(15) 0.0559(14) 0.0002(13) -0.0019(13) -0.0110(13) O2 0.0608(18) 0.0414(15) 0.0425(12) 0.0085(11) 0.0036(12) 0.0122(13) O3 0.0612(15) 0.0596(17) 0.0486(13) -0.0087(16) 0.0118(12) 0.0028(17) O4 0.0473(14) 0.0518(15) 0.0586(15) -0.0073(12) 0.0032(13) -0.0157(12) O5 0.0565(16) 0.0404(13) 0.0467(13) 0.0049(12) 0.0070(14) 0.0090(12) O6 0.0553(16) 0.0510(17) 0.0459(13) -0.0011(13) 0.0067(12) 0.0135(13) C1 0.060(3) 0.053(3) 0.046(2) -0.014(2) -0.017(2) 0.009(2) C2 0.058(3) 0.052(2) 0.076(2) -0.018(2) -0.020(3) -0.002(2) C3 0.075(3) 0.0330(18) 0.079(3) 0.002(2) 0.023(3) -0.0073(18) C4 0.073(3) 0.034(2) 0.065(2) 0.0185(18) 0.021(2) 0.006(2) C5 0.053(3) 0.078(3) 0.047(2) 0.023(2) 0.011(2) 0.018(2) C6 0.050(3) 0.094(3) 0.0332(17) -0.003(2) 0.0000(19) 0.008(2) C7 0.076(3) 0.069(3) 0.054(2) -0.024(2) -0.009(2) 0.009(3) C8 0.063(3) 0.050(3) 0.082(3) -0.024(2) -0.008(3) -0.003(2) C9 0.047(2) 0.0306(19) 0.089(3) -0.002(2) 0.021(2) -0.004(2) C10 0.057(2) 0.0360(18) 0.073(2) 0.017(2) 0.021(2) 0.000(2) C11 0.052(3) 0.068(3) 0.047(2) 0.024(2) 0.0068(19) 0.009(2) C12 0.050(2) 0.077(3) 0.0364(16) 0.0035(19) 0.0004(17) 0.019(2) O7 0.0514(13) 0.0278(11) 0.0316(10) -0.0048(12) -0.0045(10) -0.0029(14) O8 0.0709(15) 0.0277(12) 0.0376(11) 0.0042(12) 0.0044(11) -0.0072(14) O9 0.0465(14) 0.0404(15) 0.0639(18) -0.0115(13) 0.0131(12) -0.0201(12) O10 0.0589(19) 0.0311(12) 0.0387(11) -0.0034(10) 0.0141(12) -0.0064(12) O11 0.0613(15) 0.0240(12) 0.0378(11) -0.0048(14) 0.0104(11) -0.0008(17) C13 0.0266(17) 0.0254(17) 0.0327(16) 0.0034(14) -0.0015(14) 0.0014(14) C14 0.0356(18) 0.0246(15) 0.0302(14) -0.0033(12) 0.0002(17) 0.0028(17) C15 0.0317(18) 0.0195(16) 0.0317(15) 0.0025(14) -0.0080(15) 0.0052(14) C16 0.0350(18) 0.0226(16) 0.0283(16) 0.0029(14) 0.0005(15) 0.0025(15) C17 0.0365(18) 0.0228(16) 0.0270(15) -0.0011(13) -0.0034(15) 0.0074(14) C18 0.0341(18) 0.0195(17) 0.0344(14) -0.0028(13) -0.0054(13) 0.0007(14) C19 0.0270(16) 0.0315(16) 0.0389(18) 0.0017(13) 0.0022(18) 0.0062(16) C20 0.0328(19) 0.0212(16) 0.0404(18) 0.0007(15) -0.0072(17) 0.0043(14) _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 Cs1 O4 3.098(2) . ? Cs1 O7 3.103(2) . ? Cs1 O6 3.148(2) . ? Cs1 O5 3.193(2) . ? Cs1 O2 3.193(2) . ? Cs1 O11 3.374(2) 3_556 ? Cs1 O1 3.398(2) . ? Cs1 O3 3.479(2) . ? Cs1 O1 3.687(2) 4_567 ? Cs1 C10 3.691(3) . ? Cs1 C11 3.782(3) . ? Cs1 O9 3.790(2) 4_557 ? O1 C3 1.404(4) . ? O1 C2 1.424(4) . ? O1 Cs1 3.687(2) 4_467 ? O2 C4 1.410(4) . ? O2 C5 1.415(4) . ? O3 C7 1.396(4) . ? O3 C6 1.423(4) . ? O4 C8 1.406(4) . ? O4 C9 1.420(4) . ? O5 C10 1.401(4) . ? O5 C11 1.420(4) . ? O6 C1 1.412(4) . ? O6 C12 1.416(4) . ? C1 C2 1.474(5) . ? C3 C4 1.489(5) . ? C5 C6 1.470(5) . ? C7 C8 1.497(5) . ? C9 C10 1.486(4) . ? C11 C12 1.476(5) . ? O7 C20 1.260(3) . ? O8 C20 1.249(3) . ? O9 C19 1.207(3) . ? O9 Cs1 3.790(2) 4_457 ? O10 C19 1.324(3) . ? O11 C17 1.363(3) . ? O11 Cs1 3.374(2) 3_546 ? C13 C14 1.390(4) . ? C13 C18 1.391(4) . ? C13 C19 1.498(4) . ? C14 C15 1.391(4) . ? C15 C16 1.385(4) . ? C15 C20 1.521(4) . ? C16 C17 1.388(4) . ? C17 C18 1.386(4) . ? 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 O4 Cs1 O7 71.92(6) . . ? O4 Cs1 O6 103.28(6) . . ? O7 Cs1 O6 128.63(5) . . ? O4 Cs1 O5 53.73(6) . . ? O7 Cs1 O5 93.76(5) . . ? O6 Cs1 O5 52.31(6) . . ? O4 Cs1 O2 98.94(6) . . ? O7 Cs1 O2 129.91(5) . . ? O6 Cs1 O2 101.45(6) . . ? O5 Cs1 O2 120.80(6) . . ? O4 Cs1 O11 102.64(6) . 3_556 ? O7 Cs1 O11 63.65(6) . 3_556 ? O6 Cs1 O11 153.88(7) . 3_556 ? O5 Cs1 O11 153.01(6) . 3_556 ? O2 Cs1 O11 71.27(6) . 3_556 ? O4 Cs1 O1 117.10(6) . . ? O7 Cs1 O1 170.98(6) . . ? O6 Cs1 O1 51.29(6) . . ? O5 Cs1 O1 91.92(5) . . ? O2 Cs1 O1 51.42(5) . . ? O11 Cs1 O1 112.49(6) 3_556 . ? O4 Cs1 O3 50.78(7) . . ? O7 Cs1 O3 96.71(6) . . ? O6 Cs1 O3 120.05(6) . . ? O5 Cs1 O3 94.25(6) . . ? O2 Cs1 O3 49.89(7) . . ? O11 Cs1 O3 75.23(6) 3_556 . ? O1 Cs1 O3 89.85(6) . . ? O4 Cs1 O1 159.47(6) . 4_567 ? O7 Cs1 O1 92.59(5) . 4_567 ? O6 Cs1 O1 75.52(6) . 4_567 ? O5 Cs1 O1 116.16(5) . 4_567 ? O2 Cs1 O1 101.39(6) . 4_567 ? O11 Cs1 O1 81.32(5) 3_556 4_567 ? O1 Cs1 O1 78.60(3) . 4_567 ? O3 Cs1 O1 147.52(6) . 4_567 ? O4 Cs1 C10 39.68(7) . . ? O7 Cs1 C10 73.30(7) . . ? O6 Cs1 C10 73.13(7) . . ? O5 Cs1 C10 21.99(6) . . ? O2 Cs1 C10 129.69(7) . . ? O11 Cs1 C10 131.22(7) 3_556 . ? O1 Cs1 C10 113.18(7) . . ? O3 Cs1 C10 88.65(7) . . ? O1 Cs1 C10 123.82(7) 4_567 . ? O4 Cs1 C11 74.04(7) . . ? O7 Cs1 C11 95.39(7) . . ? O6 Cs1 C11 38.55(8) . . ? O5 Cs1 C11 21.42(7) . . ? O2 Cs1 C11 130.30(7) . . ? O11 Cs1 C11 158.27(8) 3_556 . ? O1 Cs1 C11 87.36(7) . . ? O3 Cs1 C11 115.15(7) . . ? O1 Cs1 C11 94.74(7) 4_567 . ? C10 Cs1 C11 36.67(8) . . ? O4 Cs1 O9 96.22(6) . 4_557 ? O7 Cs1 O9 56.91(5) . 4_557 ? O6 Cs1 O9 73.57(5) . 4_557 ? O5 Cs1 O9 67.99(5) . 4_557 ? O2 Cs1 O9 164.79(6) . 4_557 ? O11 Cs1 O9 106.68(6) 3_556 4_557 ? O1 Cs1 O9 119.38(5) . 4_557 ? O3 Cs1 O9 145.07(6) . 4_557 ? O1 Cs1 O9 63.57(5) 4_567 4_557 ? C10 Cs1 O9 63.42(7) . 4_557 ? C11 Cs1 O9 53.45(7) . 4_557 ? C3 O1 C2 112.0(3) . . ? C3 O1 Cs1 98.78(17) . . ? C2 O1 Cs1 101.45(18) . . ? C3 O1 Cs1 112.90(19) . 4_467 ? C2 O1 Cs1 96.19(18) . 4_467 ? Cs1 O1 Cs1 134.43(7) . 4_467 ? C4 O2 C5 112.4(3) . . ? C4 O2 Cs1 122.16(19) . . ? C5 O2 Cs1 124.3(2) . . ? C7 O3 C6 112.0(3) . . ? C7 O3 Cs1 98.2(2) . . ? C6 O3 Cs1 98.80(18) . . ? C8 O4 C9 112.8(3) . . ? C8 O4 Cs1 126.3(2) . . ? C9 O4 Cs1 118.87(19) . . ? C10 O5 C11 113.0(3) . . ? C10 O5 Cs1 99.43(16) . . ? C11 O5 Cs1 103.34(18) . . ? C1 O6 C12 111.3(3) . . ? C1 O6 Cs1 124.2(2) . . ? C12 O6 Cs1 120.3(2) . . ? O6 C1 C2 109.2(3) . . ? O1 C2 C1 109.1(3) . . ? O1 C3 C4 111.3(3) . . ? O1 C3 Cs1 60.21(15) . . ? C4 C3 Cs1 88.9(2) . . ? O2 C4 C3 110.1(3) . . ? O2 C5 C6 110.8(3) . . ? O3 C6 C5 109.9(3) . . ? O3 C7 C8 109.5(3) . . ? O4 C8 C7 109.4(3) . . ? O4 C9 C10 109.3(3) . . ? O5 C10 C9 109.4(3) . . ? O5 C10 Cs1 58.58(15) . . ? C9 C10 Cs1 90.1(2) . . ? O5 C11 C12 108.8(3) . . ? O5 C11 Cs1 55.23(14) . . ? C12 C11 Cs1 89.66(19) . . ? O6 C12 C11 109.7(3) . . ? C20 O7 Cs1 125.31(18) . . ? C19 O9 Cs1 131.1(2) . 4_457 ? C17 O11 Cs1 146.4(2) . 3_546 ? C14 C13 C18 119.8(3) . . ? C14 C13 C19 121.8(3) . . ? C18 C13 C19 118.3(3) . . ? C13 C14 C15 120.3(3) . . ? C16 C15 C14 119.1(3) . . ? C16 C15 C20 120.0(3) . . ? C14 C15 C20 120.9(3) . . ? C15 C16 C17 121.2(3) . . ? O11 C17 C18 123.2(3) . . ? O11 C17 C16 117.4(3) . . ? C18 C17 C16 119.4(3) . . ? C17 C18 C13 120.2(3) . . ? O9 C19 O10 123.2(3) . . ? O9 C19 C13 123.2(3) . . ? O10 C19 C13 113.6(3) . . ? O8 C20 O7 124.8(3) . . ? O8 C20 C15 117.4(3) . . ? O7 C20 C15 117.8(3) . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.838 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.062 # Attachment '- 3-CH3-new.CIF' data_3-me-i _database_code_depnum_ccdc_archive 'CCDC 794774' #TrackingRef '- 3-CH3-new.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CROWN ETHER COMPLEX' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H31 Cs O10' _chemical_formula_weight 576.37 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2066(2) _cell_length_b 15.3598(4) _cell_length_c 18.9926(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2394.05(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4923 _cell_measurement_theta_min 2.4769 _cell_measurement_theta_max 32.6138 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.085 _exptl_crystal_size_min 0.081 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88590 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 '92mm CCD camera(sapphire) on \k-goniostat' _diffrn_measurement_device_type 'Enhance (Mo) X-ray Source' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9890 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 32.67 _reflns_number_total 6901 _reflns_number_gt 5364 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -16.00 38.00 1.0000 12.0500 omega____ theta____ kappa____ phi______ frames - 26.4706 0.0000 60.0000 54 #__ type_ start__ end____ width___ exp.time_ 2 omega -67.00 -32.00 1.0000 12.0500 omega____ theta____ kappa____ phi______ frames - -26.9393 179.0000 -180.0000 35 #__ type_ start__ end____ width___ exp.time_ 3 omega -76.00 -1.00 1.0000 12.0500 omega____ theta____ kappa____ phi______ frames - -26.9393 -38.0000 30.0000 75 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0196P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(12) _refine_ls_number_reflns 6901 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0538 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_restrained_S_all 0.870 _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 Cs1 Cs -0.10720(2) 0.164073(12) 0.900897(9) 0.03146(5) Uani 1 1 d . . . O1 O 0.1385(3) 0.00207(15) 0.93740(11) 0.0449(6) Uani 1 1 d . . . O2 O 0.1311(3) 0.07468(17) 0.79690(12) 0.0511(6) Uani 1 1 d . . . O3 O 0.1204(4) 0.26014(17) 0.78901(11) 0.0525(7) Uani 1 1 d . . . O4 O -0.0141(3) 0.36186(14) 0.89977(16) 0.0538(6) Uani 1 1 d . . . O5 O 0.0162(3) 0.28125(16) 1.03533(13) 0.0464(6) Uani 1 1 d . . . O6 O -0.0062(3) 0.09588(17) 1.04773(11) 0.0479(7) Uani 1 1 d . . . C1 C 0.0685(5) 0.0141(3) 1.05810(18) 0.0583(12) Uani 1 1 d . . . H1A H 0.0174 -0.0158 1.0973 0.070 Uiso 1 1 calc R . . H1B H 0.1830 0.0219 1.0689 0.070 Uiso 1 1 calc R . . C2 C 0.0505(5) -0.0386(2) 0.9928(2) 0.0565(11) Uani 1 1 d . . . H2A H 0.0921 -0.0969 1.0006 0.068 Uiso 1 1 calc R . . H2B H -0.0638 -0.0430 0.9802 0.068 Uiso 1 1 calc R . . C3 C 0.1313(5) -0.0460(2) 0.8739(2) 0.0528(10) Uani 1 1 d . . . H3A H 0.0187 -0.0535 0.8596 0.063 Uiso 1 1 calc R . . H3B H 0.1788 -0.1032 0.8808 0.063 Uiso 1 1 calc R . . C4 C 0.2221(4) 0.0015(3) 0.8186(2) 0.0556(11) Uani 1 1 d . . . H4A H 0.3268 0.0202 0.8369 0.067 Uiso 1 1 calc R . . H4B H 0.2414 -0.0365 0.7788 0.067 Uiso 1 1 calc R . . C5 C 0.2127(5) 0.1259(3) 0.74479(19) 0.0637(13) Uani 1 1 d . . . H5A H 0.2264 0.0921 0.7021 0.076 Uiso 1 1 calc R . . H5B H 0.3198 0.1424 0.7618 0.076 Uiso 1 1 calc R . . C6 C 0.1169(6) 0.2038(3) 0.72978(17) 0.0628(12) Uani 1 1 d . . . H6A H 0.1614 0.2335 0.6890 0.075 Uiso 1 1 calc R . . H6B H 0.0052 0.1876 0.7193 0.075 Uiso 1 1 calc R . . C7 C 0.0342(5) 0.3380(3) 0.7786(2) 0.0698(13) Uani 1 1 d . . . H7A H -0.0811 0.3253 0.7737 0.084 Uiso 1 1 calc R . . H7B H 0.0710 0.3656 0.7355 0.084 Uiso 1 1 calc R . . C8 C 0.0596(5) 0.3978(3) 0.8388(3) 0.0667(13) Uani 1 1 d . . . H8A H 0.1753 0.4060 0.8468 0.080 Uiso 1 1 calc R . . H8B H 0.0116 0.4541 0.8285 0.080 Uiso 1 1 calc R . . C9 C 0.0240(5) 0.4075(2) 0.9615(3) 0.0648(13) Uani 1 1 d . . . H9A H -0.0141 0.4671 0.9576 0.078 Uiso 1 1 calc R . . H9B H 0.1412 0.4086 0.9681 0.078 Uiso 1 1 calc R . . C10 C -0.0550(5) 0.3645(3) 1.0226(2) 0.0645(13) Uani 1 1 d . . . H10A H -0.0426 0.4007 1.0641 0.077 Uiso 1 1 calc R . . H10B H -0.1705 0.3576 1.0135 0.077 Uiso 1 1 calc R . . C11 C -0.0639(4) 0.2361(3) 1.09092(18) 0.0575(11) Uani 1 1 d . . . H11A H -0.1763 0.2251 1.0778 0.069 Uiso 1 1 calc R . . H11B H -0.0640 0.2720 1.1330 0.069 Uiso 1 1 calc R . . C12 C 0.0183(4) 0.1530(3) 1.10588(17) 0.0561(10) Uani 1 1 d . . . H12A H 0.1340 0.1627 1.1130 0.067 Uiso 1 1 calc R . . H12B H -0.0261 0.1273 1.1484 0.067 Uiso 1 1 calc R . . O7 O -0.3428(3) 0.18869(14) 0.77821(11) 0.0526(7) Uani 1 1 d . . . O8 O -0.3261(3) 0.09248(14) 0.69182(12) 0.0456(6) Uani 1 1 d . . . O9 O -0.7044(3) 0.49908(17) 0.62475(13) 0.0558(7) Uani 1 1 d . . . O10 O -0.6327(3) 0.46255(14) 0.73404(11) 0.0433(6) Uani 1 1 d . . . H10O H -0.653(6) 0.531(3) 0.760(2) 0.106(16) Uiso 1 1 d . . . C13 C -0.4106(4) 0.23568(19) 0.66350(14) 0.0285(7) Uani 1 1 d . . . C14 C -0.4895(3) 0.30916(18) 0.68737(15) 0.0289(7) Uani 1 1 d . . . H14 H -0.5018 0.3175 0.7356 0.035 Uiso 1 1 calc R . . C15 C -0.5508(4) 0.37078(19) 0.64151(15) 0.0275(7) Uani 1 1 d . . . C16 C -0.5271(4) 0.3585(2) 0.56960(16) 0.0321(8) Uani 1 1 d . . . H16 H -0.5677 0.3995 0.5382 0.038 Uiso 1 1 calc R . . C17 C -0.4445(4) 0.2866(2) 0.54373(15) 0.0344(8) Uani 1 1 d . . . C18 C -0.3870(5) 0.22441(17) 0.59098(15) 0.0326(6) Uani 1 1 d . . . H18 H -0.3329 0.1753 0.5744 0.039 Uiso 1 1 calc R . . C19 C -0.3552(3) 0.1686(2) 0.71616(14) 0.0316(7) Uani 1 1 d . . . C20 C -0.6378(4) 0.4515(2) 0.66735(17) 0.0340(8) Uani 1 1 d . . . C21 C -0.4151(6) 0.2771(2) 0.46524(15) 0.0523(10) Uani 1 1 d . . . H21A H -0.3567 0.2241 0.4564 0.078 Uiso 1 1 calc R . . H21B H -0.3522 0.3257 0.4486 0.078 Uiso 1 1 calc R . . H21C H -0.5178 0.2756 0.4410 0.078 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 Cs1 0.03258(8) 0.03190(8) 0.02991(7) -0.00107(9) -0.00172(9) -0.00265(10) O1 0.0466(16) 0.0351(12) 0.0531(13) -0.0052(11) -0.0022(12) -0.0083(13) O2 0.0334(14) 0.0690(17) 0.0509(14) -0.0064(13) 0.0076(13) 0.0003(15) O3 0.0522(15) 0.0700(17) 0.0353(12) 0.0200(12) -0.0060(15) -0.0068(17) O4 0.0506(13) 0.0381(13) 0.0727(16) 0.0016(15) -0.0083(16) -0.0090(11) O5 0.0412(14) 0.0510(16) 0.0468(14) -0.0177(12) 0.0072(12) 0.0025(13) O6 0.0527(16) 0.0624(18) 0.0284(12) 0.0038(12) -0.0062(12) -0.0073(14) C1 0.065(3) 0.066(3) 0.044(2) 0.027(2) -0.0101(19) -0.014(2) C2 0.056(2) 0.038(2) 0.075(3) 0.017(2) -0.009(2) -0.0094(19) C3 0.039(2) 0.0390(19) 0.081(3) -0.0225(19) -0.008(2) 0.0106(19) C4 0.0380(19) 0.065(3) 0.064(2) -0.037(2) -0.0039(19) 0.007(2) C5 0.047(2) 0.105(4) 0.039(2) -0.015(2) 0.0112(19) -0.017(3) C6 0.051(2) 0.107(4) 0.0296(17) 0.007(2) -0.001(2) -0.023(3) C7 0.058(2) 0.084(3) 0.067(3) 0.048(3) -0.014(2) -0.011(3) C8 0.053(3) 0.047(3) 0.101(4) 0.033(3) -0.011(2) -0.007(2) C9 0.051(2) 0.028(2) 0.115(4) -0.013(2) -0.018(3) 0.004(2) C10 0.048(2) 0.059(3) 0.086(3) -0.042(2) -0.004(2) 0.011(2) C11 0.047(2) 0.090(3) 0.0354(19) -0.028(2) 0.0070(18) -0.008(2) C12 0.0520(19) 0.090(3) 0.0261(16) -0.002(2) 0.0036(16) -0.015(2) O7 0.0768(18) 0.0457(15) 0.0352(12) -0.0027(10) -0.0153(12) 0.0194(13) O8 0.0737(18) 0.0264(12) 0.0366(12) 0.0014(10) 0.0002(13) 0.0053(13) O9 0.0642(16) 0.0466(15) 0.0564(15) -0.0019(13) -0.0107(13) 0.0258(15) O10 0.0647(17) 0.0269(11) 0.0381(12) -0.0037(9) 0.0102(13) 0.0055(13) C13 0.0268(16) 0.0283(15) 0.0304(14) 0.0000(12) -0.0024(14) -0.0058(15) C14 0.0318(15) 0.0281(16) 0.0266(14) 0.0000(12) 0.0015(13) -0.0030(14) C15 0.0296(15) 0.0220(14) 0.0309(15) 0.0011(12) -0.0003(13) -0.0061(13) C16 0.0372(17) 0.0283(18) 0.0307(15) 0.0062(13) -0.0032(14) -0.0010(15) C17 0.043(2) 0.0337(18) 0.0266(15) -0.0065(14) 0.0014(14) -0.0055(16) C18 0.0385(15) 0.0224(13) 0.0368(16) -0.0058(13) 0.001(2) -0.0021(16) C19 0.0288(16) 0.0305(16) 0.0356(14) 0.0001(16) 0.0001(12) -0.0012(17) C20 0.0286(19) 0.0253(16) 0.0482(19) 0.0028(14) 0.0012(15) -0.0057(14) C21 0.075(3) 0.052(2) 0.0291(15) -0.0018(15) 0.005(2) 0.003(2) _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 Cs1 O9 3.008(2) 3_446 ? Cs1 O7 3.051(2) . ? Cs1 O6 3.092(2) . ? Cs1 O2 3.100(2) . ? Cs1 O4 3.133(2) . ? Cs1 O3 3.191(3) . ? Cs1 O1 3.277(2) . ? Cs1 O5 3.284(2) . ? Cs1 O5 3.424(2) 4_457 ? Cs1 C7 3.725(4) . ? Cs1 C6 3.784(4) . ? Cs1 C11 3.792(3) . ? O1 C3 1.415(4) . ? O1 C2 1.421(4) . ? O2 C4 1.411(4) . ? O2 C5 1.431(4) . ? O3 C7 1.403(5) . ? O3 C6 1.419(4) . ? O4 C9 1.401(5) . ? O4 C8 1.419(5) . ? O5 C11 1.424(4) . ? O5 C10 1.426(4) . ? O5 Cs1 3.424(2) 4_557 ? O6 C1 1.412(4) . ? O6 C12 1.425(4) . ? C1 C2 1.489(5) . ? C3 C4 1.480(5) . ? C5 C6 1.460(6) . ? C7 C8 1.482(6) . ? C9 C10 1.486(6) . ? C11 C12 1.472(5) . ? O7 C19 1.223(3) . ? O8 C19 1.279(4) . ? O9 C20 1.219(4) . ? O9 Cs1 3.008(2) 3_456 ? O10 C20 1.279(4) . ? C13 C14 1.378(4) . ? C13 C18 1.402(4) . ? C13 C19 1.507(4) . ? C14 C15 1.381(4) . ? C15 C16 1.392(4) . ? C15 C20 1.513(4) . ? C16 C17 1.385(4) . ? C17 C18 1.394(4) . ? C17 C21 1.517(4) . ? 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 O9 Cs1 O7 69.82(6) 3_446 . ? O9 Cs1 O6 89.91(7) 3_446 . ? O7 Cs1 O6 154.23(7) . . ? O9 Cs1 O2 81.25(7) 3_446 . ? O7 Cs1 O2 88.16(6) . . ? O6 Cs1 O2 104.81(7) . . ? O9 Cs1 O4 160.26(7) 3_446 . ? O7 Cs1 O4 91.68(7) . . ? O6 Cs1 O4 105.62(7) . . ? O2 Cs1 O4 105.74(7) . . ? O9 Cs1 O3 125.63(6) 3_446 . ? O7 Cs1 O3 78.75(7) . . ? O6 Cs1 O3 126.90(7) . . ? O2 Cs1 O3 53.93(6) . . ? O4 Cs1 O3 53.43(7) . . ? O9 Cs1 O1 73.19(7) 3_446 . ? O7 Cs1 O1 130.21(5) . . ? O6 Cs1 O1 52.20(6) . . ? O2 Cs1 O1 53.87(6) . . ? O4 Cs1 O1 125.99(6) . . ? O3 Cs1 O1 97.58(7) . . ? O9 Cs1 O5 138.25(7) 3_446 . ? O7 Cs1 O5 136.16(6) . . ? O6 Cs1 O5 53.26(7) . . ? O2 Cs1 O5 122.93(6) . . ? O4 Cs1 O5 53.03(7) . . ? O3 Cs1 O5 94.81(7) . . ? O1 Cs1 O5 93.55(6) . . ? O9 Cs1 O5 78.47(7) 3_446 4_457 ? O7 Cs1 O5 70.60(6) . 4_457 ? O6 Cs1 O5 90.34(6) . 4_457 ? O2 Cs1 O5 154.60(6) . 4_457 ? O4 Cs1 O5 89.13(6) . 4_457 ? O3 Cs1 O5 130.58(7) . 4_457 ? O1 Cs1 O5 131.82(6) . 4_457 ? O5 Cs1 O5 82.47(3) . 4_457 ? O9 Cs1 C7 131.53(8) 3_446 . ? O7 Cs1 C7 68.42(8) . . ? O6 Cs1 C7 136.21(8) . . ? O2 Cs1 C7 73.96(9) . . ? O4 Cs1 C7 39.15(9) . . ? O3 Cs1 C7 21.69(8) . . ? O1 Cs1 C7 118.99(8) . . ? O5 Cs1 C7 89.76(9) . . ? O5 Cs1 C7 109.02(8) 4_457 . ? O9 Cs1 C6 104.28(8) 3_446 . ? O7 Cs1 C6 68.41(8) . . ? O6 Cs1 C6 134.35(8) . . ? O2 Cs1 C6 38.52(8) . . ? O4 Cs1 C6 73.69(8) . . ? O3 Cs1 C6 21.39(7) . . ? O1 Cs1 C6 90.29(8) . . ? O5 Cs1 C6 115.44(8) . . ? O5 Cs1 C6 134.66(8) 4_457 . ? C7 Cs1 C6 36.61(10) . . ? O9 Cs1 C11 116.63(8) 3_446 . ? O7 Cs1 C11 138.59(7) . . ? O6 Cs1 C11 38.31(8) . . ? O2 Cs1 C11 132.59(7) . . ? O4 Cs1 C11 72.58(8) . . ? O3 Cs1 C11 116.37(8) . . ? O1 Cs1 C11 87.86(7) . . ? O5 Cs1 C11 21.73(7) . . ? O5 Cs1 C11 71.11(6) 4_457 . ? C7 Cs1 C11 110.80(10) . . ? C6 Cs1 C11 136.47(9) . . ? C3 O1 C2 112.3(3) . . ? C3 O1 Cs1 100.94(18) . . ? C2 O1 Cs1 100.22(19) . . ? C4 O2 C5 113.1(3) . . ? C4 O2 Cs1 120.0(2) . . ? C5 O2 Cs1 119.5(2) . . ? C7 O3 C6 113.4(3) . . ? C7 O3 Cs1 101.1(2) . . ? C6 O3 Cs1 103.5(2) . . ? C9 O4 C8 113.1(3) . . ? C9 O4 Cs1 122.3(2) . . ? C8 O4 Cs1 119.2(2) . . ? C11 O5 C10 111.9(3) . . ? C11 O5 Cs1 99.63(18) . . ? C10 O5 Cs1 103.5(2) . . ? C11 O5 Cs1 105.90(19) . 4_557 ? C10 O5 Cs1 102.1(2) . 4_557 ? Cs1 O5 Cs1 133.46(7) . 4_557 ? C1 O6 C12 112.2(3) . . ? C1 O6 Cs1 122.94(19) . . ? C12 O6 Cs1 121.9(2) . . ? O6 C1 C2 108.9(3) . . ? O1 C2 C1 109.1(3) . . ? O1 C2 Cs1 58.17(16) . . ? C1 C2 Cs1 88.3(2) . . ? O1 C3 C4 109.0(3) . . ? O1 C3 Cs1 57.66(15) . . ? C4 C3 Cs1 86.3(2) . . ? O2 C4 C3 109.5(3) . . ? O2 C5 C6 109.5(3) . . ? O3 C6 C5 109.5(3) . . ? O3 C6 Cs1 55.08(17) . . ? C5 C6 Cs1 87.8(2) . . ? O3 C7 C8 110.4(3) . . ? O3 C7 Cs1 57.19(18) . . ? C8 C7 Cs1 90.4(2) . . ? O4 C8 C7 109.2(3) . . ? O4 C9 C10 109.5(3) . . ? O5 C10 C9 110.7(3) . . ? O5 C10 Cs1 55.52(16) . . ? C9 C10 Cs1 86.3(2) . . ? O5 C11 C12 110.7(3) . . ? O5 C11 Cs1 58.64(15) . . ? C12 C11 Cs1 88.5(2) . . ? O6 C12 C11 108.6(3) . . ? C19 O7 Cs1 139.3(2) . . ? C20 O9 Cs1 147.4(2) . 3_456 ? C14 C13 C18 119.3(3) . . ? C14 C13 C19 118.9(2) . . ? C18 C13 C19 121.7(3) . . ? C13 C14 C15 121.7(3) . . ? C14 C15 C16 118.4(3) . . ? C14 C15 C20 121.9(3) . . ? C16 C15 C20 119.7(3) . . ? C17 C16 C15 121.6(3) . . ? C16 C17 C18 118.9(3) . . ? C16 C17 C21 120.2(3) . . ? C18 C17 C21 120.9(3) . . ? C17 C18 C13 120.1(3) . . ? O7 C19 O8 124.3(3) . . ? O7 C19 C13 119.5(3) . . ? O8 C19 C13 116.2(2) . . ? O9 C20 O10 126.3(3) . . ? O9 C20 C15 119.2(3) . . ? O10 C20 C15 114.5(3) . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.300 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.076 # Attachment '- 4-Br-new.cif' data_5briso_1 _database_code_depnum_ccdc_archive 'CCDC 794775' #TrackingRef '- 4-Br-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CROWN ETHER COMPLEX' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 Br Cs O10' _chemical_formula_weight 641.23 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2041(2) _cell_length_b 15.3854(4) _cell_length_c 19.3495(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2442.36(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8411 _cell_measurement_theta_min 2.4818 _cell_measurement_theta_max 30.7991 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 3.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.27410 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur S' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15842 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 30.84 _reflns_number_total 6528 _reflns_number_gt 5218 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 0.00 92.00 1.0000 20.0200 omega____ theta____ kappa____ phi______ frames - 22.1869 50.0000 100.0000 92 #__ type_ start__ end____ width___ exp.time_ 2 omega -17.00 15.00 1.0000 20.0200 omega____ theta____ kappa____ phi______ frames - 22.1869 -50.0000 134.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega 34.00 74.00 1.0000 20.0200 omega____ theta____ kappa____ phi______ frames - 22.1869 179.0000 120.0000 40 #__ type_ start__ end____ width___ exp.time_ 4 omega -8.00 69.00 1.0000 20.0200 omega____ theta____ kappa____ phi______ frames - 22.1869 77.0000 -120.0000 77 #__ type_ start__ end____ width___ exp.time_ 5 omega -48.00 2.00 1.0000 20.0200 omega____ theta____ kappa____ phi______ frames - 22.1869 -50.0000 134.0000 50 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0764P)^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 riding _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 0.05(2) _refine_ls_number_reflns 6528 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.005 _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 Cs1 Cs 0.11236(4) 0.66474(2) 0.901661(18) 0.03519(10) Uani 1 1 d . . . O1 O -0.0081(6) 0.7797(3) 1.0346(3) 0.0525(12) Uani 1 1 d . . . O2 O 0.0171(6) 0.8630(3) 0.9020(4) 0.0622(14) Uani 1 1 d . . . O3 O -0.1202(8) 0.7624(3) 0.7935(2) 0.0596(12) Uani 1 1 d . . . O4 O -0.1275(7) 0.5779(4) 0.7989(3) 0.0655(14) Uani 1 1 d . . . O5 O -0.1293(7) 0.5019(3) 0.9358(3) 0.0582(13) Uani 1 1 d . . . O6 O 0.0127(6) 0.5952(3) 1.0464(2) 0.0527(12) Uani 1 1 d . . . C1 C -0.0123(9) 0.6494(5) 1.1036(4) 0.060(2) Uani 1 1 d . . . H1A H 0.0349 0.6235 1.1447 0.072 Uiso 1 1 calc R . . H1B H -0.1280 0.6578 1.1115 0.072 Uiso 1 1 calc R . . C2 C 0.0679(9) 0.7344(6) 1.0885(4) 0.065(2) Uani 1 1 d . . . H2A H 0.0662 0.7700 1.1298 0.078 Uiso 1 1 calc R . . H2B H 0.1809 0.7241 1.0763 0.078 Uiso 1 1 calc R . . C3 C 0.0640(10) 0.8621(5) 1.0221(5) 0.072(3) Uani 1 1 d . . . H3A H 0.1784 0.8547 1.0109 0.087 Uiso 1 1 calc R . . H3B H 0.0564 0.8977 1.0634 0.087 Uiso 1 1 calc R . . C4 C -0.0224(11) 0.9070(5) 0.9628(5) 0.067(2) Uani 1 1 d . . . H4A H -0.1394 0.9059 0.9701 0.080 Uiso 1 1 calc R . . H4B H 0.0122 0.9672 0.9597 0.080 Uiso 1 1 calc R . . C5 C -0.0520(13) 0.8973(6) 0.8442(7) 0.093(4) Uani 1 1 d . . . H5A H -0.0024 0.9533 0.8347 0.112 Uiso 1 1 calc R . . H5B H -0.1672 0.9070 0.8527 0.112 Uiso 1 1 calc R . . C6 C -0.0335(10) 0.8409(6) 0.7830(5) 0.083(3) Uani 1 1 d . . . H6A H -0.0753 0.8704 0.7424 0.100 Uiso 1 1 calc R . . H6B H 0.0809 0.8283 0.7754 0.100 Uiso 1 1 calc R . . C7 C -0.1105(12) 0.7112(7) 0.7345(4) 0.079(3) Uani 1 1 d . . . H7A H 0.0022 0.6966 0.7248 0.095 Uiso 1 1 calc R . . H7B H -0.1548 0.7421 0.6951 0.095 Uiso 1 1 calc R . . C8 C -0.2103(10) 0.6276(8) 0.7483(4) 0.080(3) Uani 1 1 d . . . H8A H -0.3185 0.6425 0.7647 0.096 Uiso 1 1 calc R . . H8B H -0.2213 0.5943 0.7060 0.096 Uiso 1 1 calc R . . C9 C -0.2143(9) 0.5039(6) 0.8197(5) 0.065(2) Uani 1 1 d . . . H9A H -0.2330 0.4664 0.7802 0.078 Uiso 1 1 calc R . . H9B H -0.3193 0.5210 0.8382 0.078 Uiso 1 1 calc R . . C10 C -0.1246(11) 0.4577(4) 0.8712(5) 0.067(2) Uani 1 1 d . . . H10A H -0.1703 0.3999 0.8766 0.081 Uiso 1 1 calc R . . H10B H -0.0122 0.4515 0.8563 0.081 Uiso 1 1 calc R . . C11 C -0.0474(10) 0.4600(4) 0.9902(5) 0.063(2) Uani 1 1 d . . . H11A H 0.0668 0.4529 0.9785 0.076 Uiso 1 1 calc R . . H11B H -0.0940 0.4028 0.9976 0.076 Uiso 1 1 calc R . . C12 C -0.0622(11) 0.5109(5) 1.0523(5) 0.069(2) Uani 1 1 d . . . H12A H -0.0118 0.4796 1.0903 0.082 Uiso 1 1 calc R . . H12B H -0.1767 0.5182 1.0633 0.082 Uiso 1 1 calc R . . O7 O 0.3058(7) 0.5032(3) 0.8737(3) 0.0664(15) Uani 1 1 d . . . O8 O 0.3636(7) 0.4634(2) 0.7639(2) 0.0502(12) Uani 1 1 d . . . O9 O 0.6551(7) 0.1904(3) 0.7198(3) 0.0606(14) Uani 1 1 d . . . O10 O 0.6713(7) 0.0944(3) 0.8062(3) 0.0576(13) Uani 1 1 d . . . H10O H 0.6991 0.0608 0.7755 0.086 Uiso 1 1 calc R . . Br1 Br 0.60425(16) 0.27882(6) 1.04445(4) 0.0796(3) Uani 1 1 d . . . C13 C 0.4543(7) 0.3738(4) 0.8547(3) 0.0337(12) Uani 1 1 d . . . C14 C 0.5101(7) 0.3110(3) 0.8095(3) 0.0335(12) Uani 1 1 d . . . H14 H 0.4935 0.3183 0.7623 0.040 Uiso 1 1 calc R . . C15 C 0.5906(7) 0.2371(3) 0.8330(3) 0.0307(11) Uani 1 1 d . . . C16 C 0.6181(8) 0.2274(3) 0.9036(3) 0.0410(12) Uani 1 1 d . . . H16 H 0.6709 0.1782 0.9204 0.049 Uiso 1 1 calc R . . C17 C 0.5664(9) 0.2911(4) 0.9478(3) 0.0455(15) Uani 1 1 d . . . C18 C 0.4799(8) 0.3632(4) 0.9256(3) 0.0402(14) Uani 1 1 d . . . H18 H 0.4398 0.4036 0.9571 0.048 Uiso 1 1 calc R . . C19 C 0.3661(8) 0.4530(4) 0.8293(3) 0.0400(13) Uani 1 1 d . . . C20 C 0.6434(6) 0.1698(4) 0.7802(3) 0.0372(12) 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 Cs1 0.03550(15) 0.03781(16) 0.03225(16) -0.00064(15) 0.00227(15) 0.00188(15) O1 0.046(3) 0.061(3) 0.050(3) -0.028(2) -0.006(2) 0.002(2) O2 0.055(3) 0.041(2) 0.091(4) 0.017(3) 0.009(3) 0.0111(18) O3 0.056(3) 0.082(3) 0.041(3) 0.020(2) 0.001(3) 0.003(3) O4 0.039(3) 0.100(4) 0.058(3) -0.015(3) -0.005(3) -0.007(3) O5 0.072(3) 0.035(2) 0.067(3) -0.007(2) 0.018(3) -0.004(2) O6 0.062(3) 0.063(3) 0.033(2) 0.008(2) 0.011(2) 0.013(2) C1 0.064(4) 0.089(6) 0.028(3) -0.002(4) -0.001(3) 0.019(4) C2 0.047(4) 0.102(6) 0.044(4) -0.038(4) -0.015(3) 0.017(4) C3 0.055(4) 0.061(5) 0.101(7) -0.037(5) 0.007(4) -0.016(3) C4 0.062(5) 0.039(4) 0.099(7) -0.017(4) 0.023(5) -0.007(3) C5 0.084(6) 0.050(5) 0.146(11) 0.046(6) 0.041(7) 0.016(4) C6 0.056(4) 0.102(7) 0.091(7) 0.067(7) 0.022(4) 0.020(5) C7 0.055(4) 0.153(9) 0.030(4) 0.013(5) 0.000(4) 0.032(6) C8 0.046(4) 0.153(9) 0.042(5) -0.026(5) -0.012(4) 0.023(5) C9 0.042(4) 0.082(5) 0.072(6) -0.051(5) 0.006(4) -0.020(4) C10 0.065(5) 0.043(4) 0.094(6) -0.038(4) 0.015(5) -0.012(4) C11 0.060(4) 0.037(4) 0.092(6) 0.014(4) 0.015(4) 0.016(3) C12 0.079(6) 0.070(5) 0.057(5) 0.032(4) 0.006(4) 0.011(4) O7 0.091(4) 0.048(3) 0.061(3) -0.001(3) 0.013(3) 0.031(3) O8 0.082(3) 0.0248(18) 0.044(3) 0.0020(17) -0.013(3) 0.004(2) O9 0.090(4) 0.052(3) 0.040(3) 0.010(2) 0.021(3) 0.023(2) O10 0.096(4) 0.032(2) 0.045(3) -0.002(2) -0.002(3) 0.007(2) Br1 0.1323(8) 0.0725(5) 0.0338(4) 0.0027(3) -0.0148(5) 0.0021(6) C13 0.037(3) 0.030(3) 0.035(3) 0.002(2) -0.003(2) -0.001(2) C14 0.043(3) 0.030(3) 0.027(3) 0.003(2) -0.002(2) -0.005(2) C15 0.033(3) 0.026(2) 0.033(3) 0.001(2) -0.002(2) -0.005(2) C16 0.053(3) 0.032(2) 0.037(3) 0.008(3) -0.008(4) -0.003(3) C17 0.060(4) 0.041(3) 0.035(3) 0.006(3) -0.006(3) -0.003(3) C18 0.053(4) 0.032(3) 0.035(3) -0.007(2) 0.002(3) -0.007(2) C19 0.042(3) 0.031(3) 0.047(4) -0.001(2) 0.000(3) -0.011(2) C20 0.038(3) 0.034(3) 0.039(3) -0.001(3) 0.001(2) -0.004(3) _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 Cs1 O7 2.998(5) . ? Cs1 O9 3.053(5) 3_656 ? Cs1 O4 3.101(5) . ? Cs1 O6 3.107(5) . ? Cs1 O2 3.148(4) . ? Cs1 O3 3.206(5) . ? Cs1 O5 3.262(5) . ? Cs1 O1 3.275(4) . ? Cs1 O1 3.456(5) 4_567 ? Cs1 C6 3.749(8) . ? Cs1 C10 3.778(7) . ? Cs1 C7 3.783(7) . ? O1 C2 1.400(9) . ? O1 C3 1.420(9) . ? O1 Cs1 3.456(5) 4_467 ? O2 C5 1.360(12) . ? O2 C4 1.396(10) . ? O3 C7 1.390(9) . ? O3 C6 1.416(10) . ? O4 C9 1.401(10) . ? O4 C8 1.415(10) . ? O5 C11 1.406(10) . ? O5 C10 1.424(9) . ? O6 C1 1.402(8) . ? O6 C12 1.440(10) . ? C1 C2 1.493(12) . ? C3 C4 1.516(13) . ? C5 C6 1.477(14) . ? C7 C8 1.548(14) . ? C9 C10 1.427(12) . ? C11 C12 1.439(12) . ? O7 C19 1.257(8) . ? O8 C19 1.275(7) . ? O9 C20 1.214(7) . ? O9 Cs1 3.053(5) 3_646 ? O10 C20 1.286(7) . ? Br1 C17 1.905(7) . ? C13 C14 1.381(8) . ? C13 C18 1.397(9) . ? C13 C19 1.501(8) . ? C14 C15 1.392(7) . ? C15 C16 1.392(8) . ? C15 C20 1.518(8) . ? C16 C17 1.369(9) . ? C17 C18 1.385(9) . ? 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 O7 Cs1 O9 68.72(15) . 3_656 ? O7 Cs1 O4 82.11(16) . . ? O9 Cs1 O4 87.63(14) 3_656 . ? O7 Cs1 O6 90.97(14) . . ? O9 Cs1 O6 154.53(14) 3_656 . ? O4 Cs1 O6 105.22(15) . . ? O7 Cs1 O2 159.17(15) . . ? O9 Cs1 O2 91.80(14) 3_656 . ? O4 Cs1 O2 105.15(16) . . ? O6 Cs1 O2 105.45(14) . . ? O7 Cs1 O3 125.85(15) . . ? O9 Cs1 O3 78.98(15) 3_656 . ? O4 Cs1 O3 53.54(14) . . ? O6 Cs1 O3 126.37(14) . . ? O2 Cs1 O3 53.09(16) . . ? O7 Cs1 O5 73.86(15) . . ? O9 Cs1 O5 129.42(12) 3_656 . ? O4 Cs1 O5 54.06(14) . . ? O6 Cs1 O5 52.64(14) . . ? O2 Cs1 O5 126.34(13) . . ? O3 Cs1 O5 97.49(15) . . ? O7 Cs1 O1 138.55(14) . . ? O9 Cs1 O1 136.35(13) 3_656 . ? O4 Cs1 O1 123.04(13) . . ? O6 Cs1 O1 53.03(13) . . ? O2 Cs1 O1 53.15(15) . . ? O3 Cs1 O1 94.58(13) . . ? O5 Cs1 O1 94.14(13) . . ? O7 Cs1 O1 78.02(15) . 4_567 ? O9 Cs1 O1 71.31(13) 3_656 4_567 ? O4 Cs1 O1 155.11(12) . 4_567 ? O6 Cs1 O1 90.05(13) . 4_567 ? O2 Cs1 O1 89.04(13) . 4_567 ? O3 Cs1 O1 130.77(14) . 4_567 ? O5 Cs1 O1 131.70(14) . 4_567 ? O1 Cs1 O1 81.84(6) . 4_567 ? O7 Cs1 C6 131.1(2) . . ? O9 Cs1 C6 68.56(17) 3_656 . ? O4 Cs1 C6 73.5(2) . . ? O6 Cs1 C6 135.81(17) . . ? O2 Cs1 C6 38.9(2) . . ? O3 Cs1 C6 21.75(18) . . ? O5 Cs1 C6 119.02(18) . . ? O1 Cs1 C6 89.7(2) . . ? O1 Cs1 C6 109.11(17) 4_567 . ? O7 Cs1 C10 62.96(18) . . ? O9 Cs1 C10 108.08(15) 3_656 . ? O4 Cs1 C10 37.80(19) . . ? O6 Cs1 C10 73.44(17) . . ? O2 Cs1 C10 133.58(18) . . ? O3 Cs1 C10 89.26(19) . . ? O5 Cs1 C10 21.80(16) . . ? O1 Cs1 C10 115.01(15) . . ? O1 Cs1 C10 136.70(17) 4_567 . ? C6 Cs1 C10 110.5(2) . . ? O7 Cs1 C7 104.94(18) . . ? O9 Cs1 C7 67.64(18) 3_656 . ? O4 Cs1 C7 39.3(2) . . ? O6 Cs1 C7 135.09(18) . . ? O2 Cs1 C7 72.5(2) . . ? O3 Cs1 C7 20.91(16) . . ? O5 Cs1 C7 91.4(2) . . ? O1 Cs1 C7 115.07(16) . . ? O1 Cs1 C7 133.92(18) 4_567 . ? C6 Cs1 C7 35.5(2) . . ? C10 Cs1 C7 77.1(2) . . ? C2 O1 C3 112.7(6) . . ? C2 O1 Cs1 100.5(4) . . ? C3 O1 Cs1 102.9(4) . . ? C2 O1 Cs1 105.0(4) . 4_467 ? C3 O1 Cs1 102.4(4) . 4_467 ? Cs1 O1 Cs1 133.30(14) . 4_467 ? C5 O2 C4 114.0(6) . . ? C5 O2 Cs1 118.6(6) . . ? C4 O2 Cs1 122.0(5) . . ? C7 O3 C6 109.7(7) . . ? C7 O3 Cs1 103.6(4) . . ? C6 O3 Cs1 101.2(4) . . ? C9 O4 C8 113.2(7) . . ? C9 O4 Cs1 119.2(4) . . ? C8 O4 Cs1 121.0(5) . . ? C11 O5 C10 115.2(6) . . ? C11 O5 Cs1 102.3(4) . . ? C10 O5 Cs1 99.9(4) . . ? C1 O6 C12 114.2(6) . . ? C1 O6 Cs1 123.1(4) . . ? C12 O6 Cs1 119.7(4) . . ? O6 C1 C2 107.5(6) . . ? O1 C2 C1 112.7(6) . . ? O1 C2 Cs1 58.2(3) . . ? C1 C2 Cs1 89.0(4) . . ? O1 C3 C4 110.0(6) . . ? O1 C3 Cs1 56.1(3) . . ? C4 C3 Cs1 87.1(4) . . ? O2 C4 C3 107.9(6) . . ? O2 C5 C6 112.8(7) . . ? O3 C6 C5 109.5(7) . . ? O3 C6 Cs1 57.0(3) . . ? C5 C6 Cs1 88.1(5) . . ? O3 C7 C8 107.4(6) . . ? O3 C7 Cs1 55.5(3) . . ? C8 C7 Cs1 87.2(4) . . ? O4 C8 C7 108.3(6) . . ? O4 C9 C10 110.1(6) . . ? O5 C10 C9 111.1(6) . . ? O5 C10 Cs1 58.3(3) . . ? C9 C10 Cs1 87.4(4) . . ? O5 C11 C12 109.6(6) . . ? O5 C11 Cs1 56.6(3) . . ? C12 C11 Cs1 87.4(4) . . ? C11 C12 O6 112.7(7) . . ? C19 O7 Cs1 147.3(5) . . ? C20 O9 Cs1 139.2(4) . 3_646 ? C14 C13 C18 119.4(5) . . ? C14 C13 C19 121.3(5) . . ? C18 C13 C19 119.3(5) . . ? C13 C14 C15 121.4(5) . . ? C14 C15 C16 119.1(5) . . ? C14 C15 C20 118.2(5) . . ? C16 C15 C20 122.7(5) . . ? C17 C16 C15 119.0(5) . . ? C16 C17 C18 122.6(6) . . ? C16 C17 Br1 119.5(5) . . ? C18 C17 Br1 117.8(5) . . ? C17 C18 C13 118.3(6) . . ? O7 C19 O8 126.5(6) . . ? O7 C19 C13 117.7(6) . . ? O8 C19 C13 115.8(5) . . ? O9 C20 O10 126.8(6) . . ? O9 C20 C15 119.5(5) . . ? O10 C20 C15 113.7(5) . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.409 _refine_diff_density_min -0.922 _refine_diff_density_rms 0.126 # Attachment '- 5-OCH3-new.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 794776' #TrackingRef '- 5-OCH3-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CROWN ETHER COMPLEX' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H31 Cs O11' _chemical_formula_weight 592.37 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1436(2) _cell_length_b 14.9847(2) _cell_length_c 20.1066(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2453.60(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11251 _cell_measurement_theta_min 2.4372 _cell_measurement_theta_max 28.9889 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.086 _exptl_crystal_size_min 0.078 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60136 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34 (release 24-02-2009 CrysAlis171 .NET) (compiled Feb 24 2009,11:20:51) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Xcalibur S' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16810 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.05 _reflns_number_total 5785 _reflns_number_gt 5160 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -7.00 90.00 1.0000 14.9300 omega____ theta____ kappa____ phi______ frames - 18.0642 38.0000 -120.0000 97 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 85.00 1.0000 14.9300 omega____ theta____ kappa____ phi______ frames - 18.0642 77.0000 -30.0000 97 #__ type_ start__ end____ width___ exp.time_ 3 omega 49.00 94.00 1.0000 14.9300 omega____ theta____ kappa____ phi______ frames - 18.0642 -165.0000 150.0000 45 #__ type_ start__ end____ width___ exp.time_ 4 omega -50.00 44.00 1.0000 14.9300 omega____ theta____ kappa____ phi______ frames - 18.0642 -38.0000 60.0000 94 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0288P)^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 SHELXL _refine_ls_extinction_coef 0.00095(19) _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 -0.007(12) _refine_ls_number_reflns 5785 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0529 _refine_ls_wR_factor_gt 0.0517 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.008 _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 Cs1 Cs 0.13068(2) 0.661193(10) 0.905840(8) 0.03442(6) Uani 1 1 d . . . O1 O 0.0065(3) 0.77832(15) 1.03483(12) 0.0521(6) Uani 1 1 d . . . O2 O 0.0367(3) 0.86563(14) 0.90882(16) 0.0671(7) Uani 1 1 d . . . O3 O -0.0996(3) 0.76746(19) 0.80338(12) 0.0707(8) Uani 1 1 d . . . O4 O -0.1146(3) 0.57846(19) 0.80661(12) 0.0727(8) Uani 1 1 d . . . O5 O -0.1130(3) 0.49640(13) 0.93706(12) 0.0615(6) Uani 1 1 d . . . O6 O 0.0312(3) 0.58867(16) 1.04446(11) 0.0557(6) Uani 1 1 d . . . C1 C 0.0018(4) 0.6449(3) 1.09951(17) 0.0671(11) Uani 1 1 d . . . H1A H 0.0442 0.6175 1.1397 0.081 Uiso 1 1 calc R . . H1B H -0.1154 0.6539 1.1050 0.081 Uiso 1 1 calc R . . C2 C 0.0835(4) 0.7311(3) 1.08815(17) 0.0705(12) Uani 1 1 d . . . H2A H 0.0784 0.7667 1.1284 0.085 Uiso 1 1 calc R . . H2B H 0.1982 0.7210 1.0775 0.085 Uiso 1 1 calc R . . C3 C 0.0791(5) 0.8628(3) 1.0248(2) 0.0750(13) Uani 1 1 d . . . H3A H 0.1950 0.8555 1.0153 0.090 Uiso 1 1 calc R . . H3B H 0.0688 0.8981 1.0650 0.090 Uiso 1 1 calc R . . C4 C -0.0004(5) 0.9096(2) 0.9695(3) 0.0813(15) Uani 1 1 d . . . H4A H -0.1183 0.9104 0.9763 0.098 Uiso 1 1 calc R . . H4B H 0.0381 0.9708 0.9677 0.098 Uiso 1 1 calc R . . C5 C -0.0356(6) 0.9063(3) 0.8529(3) 0.0940(18) Uani 1 1 d . . . H5A H 0.0147 0.9640 0.8450 0.113 Uiso 1 1 calc R . . H5B H -0.1520 0.9154 0.8607 0.113 Uiso 1 1 calc R . . C6 C -0.0122(5) 0.8490(4) 0.7952(2) 0.0981(18) Uani 1 1 d . . . H6A H -0.0509 0.8794 0.7556 0.118 Uiso 1 1 calc R . . H6B H 0.1038 0.8366 0.7895 0.118 Uiso 1 1 calc R . . C7 C -0.1030(6) 0.7130(4) 0.7462(2) 0.105(2) Uani 1 1 d . . . H7A H 0.0081 0.6963 0.7340 0.125 Uiso 1 1 calc R . . H7B H -0.1508 0.7457 0.7094 0.125 Uiso 1 1 calc R . . C8 C -0.2006(5) 0.6320(4) 0.7594(2) 0.0923(18) Uani 1 1 d . . . H8A H -0.3075 0.6483 0.7768 0.111 Uiso 1 1 calc R . . H8B H -0.2165 0.5989 0.7185 0.111 Uiso 1 1 calc R . . C9 C -0.2023(5) 0.5017(3) 0.8245(2) 0.0855(16) Uani 1 1 d . . . H9A H -0.2213 0.4650 0.7855 0.103 Uiso 1 1 calc R . . H9B H -0.3079 0.5183 0.8430 0.103 Uiso 1 1 calc R . . C10 C -0.1058(6) 0.4511(2) 0.8744(2) 0.0823(15) Uani 1 1 d . . . H10A H -0.1502 0.3914 0.8790 0.099 Uiso 1 1 calc R . . H10B H 0.0075 0.4462 0.8600 0.099 Uiso 1 1 calc R . . C11 C -0.0230(5) 0.4540(2) 0.9877(2) 0.0785(14) Uani 1 1 d . . . H11A H 0.0925 0.4523 0.9759 0.094 Uiso 1 1 calc R . . H11B H -0.0611 0.3931 0.9932 0.094 Uiso 1 1 calc R . . C12 C -0.0449(5) 0.5038(3) 1.0507(2) 0.0766(13) Uani 1 1 d . . . H12A H -0.1610 0.5112 1.0600 0.092 Uiso 1 1 calc R . . H12B H 0.0043 0.4710 1.0871 0.092 Uiso 1 1 calc R . . O7 O 0.3339(3) 0.48894(13) 0.88757(12) 0.0549(6) Uani 1 1 d . . . O8 O 0.3354(3) 0.44817(12) 0.78143(11) 0.0569(7) Uani 1 1 d . . . O9 O 0.6301(3) 0.17818(13) 0.70978(9) 0.0537(5) Uani 1 1 d . . . O10 O 0.7007(3) 0.08012(13) 0.78741(11) 0.0540(6) Uani 1 1 d . . . H10O H 0.682(6) 0.013(3) 0.749(2) 0.117(16) Uiso 1 1 d . . . C13 C 0.4694(3) 0.35511(15) 0.85781(13) 0.0289(6) Uani 1 1 d . . . C14 C 0.5149(3) 0.29729(17) 0.80825(13) 0.0307(6) Uani 1 1 d . . . H14 H 0.4842 0.3090 0.7646 0.037 Uiso 1 1 calc R . . C15 C 0.6069(3) 0.22099(16) 0.82267(12) 0.0294(6) Uani 1 1 d . . . C16 C 0.6550(3) 0.20536(16) 0.88779(13) 0.0330(6) Uani 1 1 d . . . H16 H 0.7156 0.1546 0.8979 0.040 Uiso 1 1 calc R . . C17 C 0.6137(4) 0.26442(16) 0.93775(13) 0.0335(6) Uani 1 1 d . . . C18 C 0.5176(3) 0.33860(19) 0.92328(12) 0.0324(6) Uani 1 1 d . . . H18 H 0.4856 0.3771 0.9571 0.039 Uiso 1 1 calc R . . C19 C 0.3711(4) 0.43824(16) 0.84253(14) 0.0362(6) Uani 1 1 d . . . C20 C 0.6482(3) 0.15628(18) 0.76792(13) 0.0344(6) Uani 1 1 d . . . C21 C 0.6240(6) 0.2957(2) 1.05395(14) 0.0630(9) Uani 1 1 d . . . H21A H 0.6574 0.3565 1.0476 0.095 Uiso 1 1 calc R . . H21B H 0.6731 0.2727 1.0938 0.095 Uiso 1 1 calc R . . H21C H 0.5066 0.2929 1.0577 0.095 Uiso 1 1 calc R . . O11 O 0.6753(3) 0.24412(14) 0.99919(10) 0.0487(6) 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 Cs1 0.03290(8) 0.03540(8) 0.03494(9) -0.00063(8) 0.00158(8) 0.00119(8) O1 0.0394(13) 0.0581(14) 0.0587(15) -0.0262(12) -0.0035(12) -0.0049(11) O2 0.0469(13) 0.0470(12) 0.107(2) 0.0212(16) 0.0118(16) 0.0066(10) O3 0.0547(18) 0.113(2) 0.0440(14) 0.0280(14) 0.0037(13) 0.0135(16) O4 0.0341(13) 0.116(2) 0.0683(17) -0.0300(15) -0.0057(14) -0.0032(16) O5 0.0555(14) 0.0353(11) 0.0937(18) -0.0091(11) 0.0185(15) 0.0072(12) O6 0.0547(15) 0.0696(16) 0.0429(13) 0.0121(11) 0.0111(12) 0.0149(12) C1 0.0496(19) 0.120(3) 0.0321(17) 0.005(2) 0.0016(17) 0.020(2) C2 0.0443(19) 0.126(3) 0.042(2) -0.039(2) -0.0079(18) 0.017(2) C3 0.048(2) 0.067(2) 0.110(3) -0.051(2) 0.006(2) -0.0105(18) C4 0.061(3) 0.0298(17) 0.153(5) -0.020(2) 0.037(3) -0.0077(18) C5 0.059(3) 0.074(3) 0.149(5) 0.059(3) 0.031(3) 0.013(2) C6 0.050(2) 0.141(4) 0.103(4) 0.094(4) 0.012(2) 0.007(3) C7 0.063(3) 0.215(6) 0.036(2) 0.015(3) 0.002(2) 0.053(4) C8 0.054(2) 0.168(5) 0.054(3) -0.046(3) -0.017(2) 0.034(3) C9 0.037(2) 0.108(4) 0.112(4) -0.075(3) 0.005(2) -0.007(2) C10 0.060(3) 0.0466(19) 0.140(4) -0.049(2) 0.045(3) -0.021(2) C11 0.069(3) 0.0397(19) 0.126(4) 0.020(2) 0.043(3) 0.0153(19) C12 0.066(3) 0.073(3) 0.091(3) 0.053(2) 0.023(2) 0.022(2) O7 0.0592(16) 0.0403(11) 0.0653(16) -0.0014(10) 0.0048(12) 0.0178(10) O8 0.086(2) 0.0305(10) 0.0538(14) 0.0019(9) -0.0308(14) 0.0081(11) O9 0.0753(14) 0.0534(12) 0.0323(10) 0.0011(9) 0.0095(13) 0.0177(14) O10 0.0835(17) 0.0334(11) 0.0450(13) -0.0088(10) -0.0177(13) 0.0155(11) C13 0.0299(13) 0.0223(13) 0.0346(14) 0.0033(10) -0.0005(11) -0.0046(10) C14 0.0334(14) 0.0301(13) 0.0287(14) 0.0060(11) -0.0031(12) -0.0010(11) C15 0.0305(15) 0.0269(12) 0.0309(13) 0.0012(10) 0.0015(12) -0.0042(11) C16 0.0352(17) 0.0239(11) 0.0400(15) 0.0020(10) -0.0032(13) 0.0007(11) C17 0.0403(16) 0.0301(12) 0.0302(13) 0.0056(10) -0.0054(14) -0.0048(14) C18 0.0353(13) 0.0299(12) 0.0320(14) -0.0028(12) 0.0042(10) -0.0036(13) C19 0.0309(13) 0.0261(12) 0.0516(17) 0.0024(12) 0.0003(17) -0.0069(15) C20 0.0279(13) 0.0366(12) 0.0386(14) -0.0054(13) -0.0004(12) -0.0046(15) C21 0.076(2) 0.080(2) 0.0331(16) -0.0075(16) -0.007(2) 0.011(2) O11 0.0689(18) 0.0450(11) 0.0321(11) -0.0012(8) -0.0115(11) 0.0109(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cs1 O9 3.044(2) 3_656 ? Cs1 O4 3.083(2) . ? Cs1 O7 3.088(2) . ? Cs1 O6 3.099(2) . ? Cs1 O2 3.158(2) . ? Cs1 O3 3.209(2) . ? Cs1 O5 3.229(2) . ? Cs1 O1 3.291(2) . ? Cs1 O1 3.407(2) 4_567 ? Cs1 C11 3.731(4) . ? Cs1 C10 3.744(3) . ? Cs1 C6 3.772(4) . ? O1 C3 1.412(4) . ? O1 C2 1.430(4) . ? O1 Cs1 3.407(2) 4_467 ? O2 C5 1.409(5) . ? O2 C4 1.419(5) . ? O3 C7 1.410(5) . ? O3 C6 1.424(5) . ? O4 C9 1.400(5) . ? O4 C8 1.427(5) . ? O5 C11 1.407(5) . ? O5 C10 1.432(4) . ? O6 C1 1.411(4) . ? O6 C12 1.420(4) . ? C1 C2 1.471(5) . ? C3 C4 1.465(6) . ? C5 C6 1.455(7) . ? C7 C8 1.474(7) . ? C9 C10 1.484(6) . ? C11 C12 1.480(6) . ? O7 C19 1.220(3) . ? O8 C19 1.271(3) . ? O9 C20 1.223(3) . ? O9 Cs1 3.044(2) 3_646 ? O10 C20 1.280(3) . ? C13 C14 1.372(4) . ? C13 C18 1.396(4) . ? C13 C19 1.512(4) . ? C14 C15 1.397(3) . ? C15 C16 1.386(4) . ? C15 C20 1.505(3) . ? C16 C17 1.380(4) . ? C17 O11 1.368(3) . ? C17 C18 1.390(4) . ? C21 O11 1.408(4) . ? 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 O9 Cs1 O4 87.36(6) 3_656 . ? O9 Cs1 O7 68.66(6) 3_656 . ? O4 Cs1 O7 86.22(7) . . ? O9 Cs1 O6 152.07(6) 3_656 . ? O4 Cs1 O6 105.76(7) . . ? O7 Cs1 O6 87.36(6) . . ? O9 Cs1 O2 95.08(6) 3_656 . ? O4 Cs1 O2 104.20(8) . . ? O7 Cs1 O2 160.55(6) . . ? O6 Cs1 O2 105.05(7) . . ? O9 Cs1 O3 80.92(6) 3_656 . ? O4 Cs1 O3 53.53(8) . . ? O7 Cs1 O3 130.66(7) . . ? O6 Cs1 O3 126.77(6) . . ? O2 Cs1 O3 52.35(8) . . ? O9 Cs1 O5 127.28(5) 3_656 . ? O4 Cs1 O5 54.57(7) . . ? O7 Cs1 O5 73.33(6) . . ? O6 Cs1 O5 52.88(7) . . ? O2 Cs1 O5 126.09(6) . . ? O3 Cs1 O5 98.35(7) . . ? O9 Cs1 O1 138.94(5) 3_656 . ? O4 Cs1 O1 121.69(6) . . ? O7 Cs1 O1 134.77(6) . . ? O6 Cs1 O1 52.98(6) . . ? O2 Cs1 O1 52.64(7) . . ? O3 Cs1 O1 93.54(7) . . ? O5 Cs1 O1 93.77(6) . . ? O9 Cs1 O1 70.75(6) 3_656 4_567 ? O4 Cs1 O1 156.25(6) . 4_567 ? O7 Cs1 O1 77.45(6) . 4_567 ? O6 Cs1 O1 90.76(6) . 4_567 ? O2 Cs1 O1 87.31(6) . 4_567 ? O3 Cs1 O1 128.14(7) . 4_567 ? O5 Cs1 O1 133.41(7) . 4_567 ? O1 Cs1 O1 81.85(3) . 4_567 ? O9 Cs1 C11 128.42(7) 3_656 . ? O4 Cs1 C11 74.56(10) . . ? O7 Cs1 C11 62.39(7) . . ? O6 Cs1 C11 39.06(9) . . ? O2 Cs1 C11 135.86(8) . . ? O3 Cs1 C11 120.03(10) . . ? O5 Cs1 C11 21.84(9) . . ? O1 Cs1 C11 89.59(8) . . ? O1 Cs1 C11 111.59(9) 4_567 . ? O9 Cs1 C10 105.71(7) 3_656 . ? O4 Cs1 C10 38.70(10) . . ? O7 Cs1 C10 63.43(8) . . ? O6 Cs1 C10 73.88(9) . . ? O2 Cs1 C10 133.96(9) . . ? O3 Cs1 C10 90.48(10) . . ? O5 Cs1 C10 22.15(8) . . ? O1 Cs1 C10 115.04(7) . . ? O1 Cs1 C10 138.13(9) 4_567 . ? C11 Cs1 C10 37.07(11) . . ? O9 Cs1 C6 71.61(8) 3_656 . ? O4 Cs1 C6 73.66(10) . . ? O7 Cs1 C6 135.97(10) . . ? O6 Cs1 C6 135.35(9) . . ? O2 Cs1 C6 38.05(11) . . ? O3 Cs1 C6 21.67(9) . . ? O5 Cs1 C6 119.72(9) . . ? O1 Cs1 C6 88.39(10) . . ? O1 Cs1 C6 106.56(8) 4_567 . ? C11 Cs1 C6 141.08(11) . . ? C10 Cs1 C6 111.68(12) . . ? C3 O1 C2 111.6(3) . . ? C3 O1 Cs1 103.7(2) . . ? C2 O1 Cs1 101.06(17) . . ? C3 O1 Cs1 100.81(19) . 4_467 ? C2 O1 Cs1 105.27(18) . 4_467 ? Cs1 O1 Cs1 133.94(7) . 4_467 ? C5 O2 C4 113.4(3) . . ? C5 O2 Cs1 120.4(3) . . ? C4 O2 Cs1 121.2(2) . . ? C7 O3 C6 114.4(4) . . ? C7 O3 Cs1 104.3(2) . . ? C6 O3 Cs1 102.0(2) . . ? C9 O4 C8 112.5(4) . . ? C9 O4 Cs1 119.6(2) . . ? C8 O4 Cs1 121.5(3) . . ? C11 O5 C10 113.7(3) . . ? C11 O5 Cs1 99.6(2) . . ? C10 O5 Cs1 99.59(19) . . ? C1 O6 C12 113.0(3) . . ? C1 O6 Cs1 122.7(2) . . ? C12 O6 Cs1 120.5(2) . . ? O6 C1 C2 109.0(3) . . ? O1 C2 C1 110.7(3) . . ? O1 C2 Cs1 57.46(14) . . ? C1 C2 Cs1 87.4(2) . . ? O1 C3 C4 110.6(3) . . ? O1 C3 Cs1 55.56(15) . . ? C4 C3 Cs1 87.3(2) . . ? O2 C4 C3 109.7(3) . . ? O2 C5 C6 109.0(3) . . ? O3 C6 C5 110.4(3) . . ? O3 C6 Cs1 56.31(16) . . ? C5 C6 Cs1 90.6(2) . . ? O3 C7 C8 109.9(3) . . ? O3 C7 Cs1 54.68(18) . . ? C8 C7 Cs1 87.2(2) . . ? O4 C8 C7 108.5(3) . . ? O4 C9 C10 108.9(3) . . ? O5 C10 C9 109.3(3) . . ? O5 C10 Cs1 58.26(15) . . ? C9 C10 Cs1 87.5(2) . . ? O5 C11 C12 109.2(3) . . ? O5 C11 Cs1 58.60(16) . . ? C12 C11 Cs1 89.9(2) . . ? O6 C12 C11 108.9(3) . . ? C19 O7 Cs1 137.9(2) . . ? C20 O9 Cs1 129.09(19) . 3_646 ? C14 C13 C18 119.8(2) . . ? C14 C13 C19 121.1(2) . . ? C18 C13 C19 119.1(2) . . ? C13 C14 C15 120.7(2) . . ? C16 C15 C14 119.0(2) . . ? C16 C15 C20 121.3(2) . . ? C14 C15 C20 119.7(2) . . ? C17 C16 C15 120.7(2) . . ? O11 C17 C16 115.2(2) . . ? O11 C17 C18 125.0(2) . . ? C16 C17 C18 119.8(2) . . ? C17 C18 C13 119.8(2) . . ? O7 C19 O8 126.0(3) . . ? O7 C19 C13 119.6(3) . . ? O8 C19 C13 114.4(2) . . ? O9 C20 O10 124.9(3) . . ? O9 C20 C15 120.0(2) . . ? O10 C20 C15 115.1(2) . . ? C17 O11 C21 118.4(2) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.413 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.058 # Attachment '- 6-NO2-new.cif' data_cset6no2iso_2 _database_code_depnum_ccdc_archive 'CCDC 794777' #TrackingRef '- 6-NO2-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CROWN ETHER COMPLEX' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 Cs N O12' _chemical_formula_weight 607.34 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1755(2) _cell_length_b 15.5119(3) _cell_length_c 19.1951(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2434.28(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5556 _cell_measurement_theta_min 2.4856 _cell_measurement_theta_max 28.8723 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 1.584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75031 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34 (release 24-02-2009 CrysAlis171 .NET) (compiled Feb 24 2009,11:20:51) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur S' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9551 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.94 _reflns_number_total 5200 _reflns_number_gt 4400 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 8.00 47.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -17.0000 -123.0000 39 #__ type_ start__ end____ width___ exp.time_ 2 omega -60.00 6.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 109.0000 77.0000 66 #__ type_ start__ end____ width___ exp.time_ 3 omega -89.00 -8.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 -38.0000 0.0000 81 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0154P)^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 SHELXL _refine_ls_extinction_coef 0.00123(12) _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 0.195(11) _refine_ls_number_reflns 5200 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0422 _refine_ls_wR_factor_gt 0.0410 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.895 _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 Cs1 Cs 0.10867(2) 0.667932(12) 0.900621(9) 0.03211(6) Uani 1 1 d . . . O1 O -0.0147(3) 0.77999(17) 1.03538(13) 0.0455(7) Uani 1 1 d . . . O2 O 0.0139(3) 0.86200(13) 0.90199(16) 0.0512(6) Uani 1 1 d . . . O3 O -0.1197(4) 0.76495(16) 0.79052(12) 0.0543(7) Uani 1 1 d . . . O4 O -0.1251(4) 0.58038(16) 0.79656(13) 0.0538(7) Uani 1 1 d . . . O5 O -0.1330(3) 0.50432(14) 0.93480(12) 0.0506(7) Uani 1 1 d . . . O6 O 0.0088(3) 0.59531(17) 1.04533(12) 0.0489(7) Uani 1 1 d . . . C1 C -0.0169(5) 0.6512(2) 1.10307(18) 0.0560(10) Uani 1 1 d . . . H1A H 0.0271 0.6252 1.1450 0.067 Uiso 1 1 calc R . . H1B H -0.1332 0.6604 1.1098 0.067 Uiso 1 1 calc R . . C2 C 0.0654(5) 0.7349(3) 1.08976(18) 0.0582(11) Uani 1 1 d . . . H2A H 0.0640 0.7694 1.1319 0.070 Uiso 1 1 calc R . . H2B H 0.1786 0.7248 1.0770 0.070 Uiso 1 1 calc R . . C3 C 0.0590(5) 0.8621(2) 1.0237(2) 0.0600(13) Uani 1 1 d . . . H3A H 0.1743 0.8547 1.0135 0.072 Uiso 1 1 calc R . . H3B H 0.0495 0.8971 1.0654 0.072 Uiso 1 1 calc R . . C4 C -0.0228(6) 0.9064(2) 0.9645(3) 0.0654(14) Uani 1 1 d . . . H4A H -0.1401 0.9072 0.9719 0.078 Uiso 1 1 calc R . . H4B H 0.0153 0.9655 0.9614 0.078 Uiso 1 1 calc R . . C5 C -0.0610(6) 0.9000(2) 0.8421(2) 0.0658(14) Uani 1 1 d . . . H5A H -0.0133 0.9562 0.8330 0.079 Uiso 1 1 calc R . . H5B H -0.1773 0.9075 0.8500 0.079 Uiso 1 1 calc R . . C6 C -0.0337(5) 0.8421(3) 0.7813(2) 0.0693(13) Uani 1 1 d . . . H6A H -0.0704 0.8703 0.7390 0.083 Uiso 1 1 calc R . . H6B H 0.0821 0.8299 0.7766 0.083 Uiso 1 1 calc R . . C7 C -0.1133(7) 0.7089(3) 0.73128(17) 0.0655(13) Uani 1 1 d . . . H7A H -0.0005 0.6939 0.7213 0.079 Uiso 1 1 calc R . . H7B H -0.1580 0.7381 0.6909 0.079 Uiso 1 1 calc R . . C8 C -0.2074(5) 0.6307(3) 0.7455(2) 0.0631(13) Uani 1 1 d . . . H8A H -0.3155 0.6460 0.7622 0.076 Uiso 1 1 calc R . . H8B H -0.2198 0.5975 0.7030 0.076 Uiso 1 1 calc R . . C9 C -0.2135(5) 0.5064(3) 0.8164(2) 0.0594(12) Uani 1 1 d . . . H9A H -0.2307 0.4697 0.7762 0.071 Uiso 1 1 calc R . . H9B H -0.3196 0.5232 0.8346 0.071 Uiso 1 1 calc R . . C10 C -0.1210(6) 0.4588(2) 0.8705(2) 0.0584(11) Uani 1 1 d . . . H10A H -0.1655 0.4012 0.8758 0.070 Uiso 1 1 calc R . . H10B H -0.0072 0.4538 0.8568 0.070 Uiso 1 1 calc R . . C11 C -0.0444(5) 0.4638(2) 0.9886(2) 0.0642(13) Uani 1 1 d . . . H11A H 0.0706 0.4611 0.9762 0.077 Uiso 1 1 calc R . . H11B H -0.0838 0.4054 0.9950 0.077 Uiso 1 1 calc R . . C12 C -0.0646(5) 0.5135(3) 1.0545(2) 0.0615(13) Uani 1 1 d . . . H12A H -0.1799 0.5201 1.0653 0.074 Uiso 1 1 calc R . . H12B H -0.0127 0.4832 1.0928 0.074 Uiso 1 1 calc R . . O7 O 0.3053(3) 0.51013(15) 0.86882(12) 0.0538(7) Uani 1 1 d . . . O8 O 0.3689(3) 0.46955(12) 0.76079(11) 0.0435(6) Uani 1 1 d . . . O9 O 0.6552(3) 0.19373(13) 0.72263(11) 0.0482(7) Uani 1 1 d . . . O10 O 0.6611(3) 0.09966(13) 0.81017(11) 0.0418(7) Uani 1 1 d . . . H10O H 0.647(7) 0.034(3) 0.774(3) 0.14(2) Uiso 1 1 d . . . O11 O 0.6448(5) 0.22665(17) 1.04734(13) 0.0858(12) Uani 1 1 d . . . O12 O 0.5323(5) 0.3488(2) 1.06202(13) 0.1051(15) Uani 1 1 d . . . N1 N 0.5805(5) 0.2909(2) 1.02535(14) 0.0550(10) Uani 1 1 d . . . C13 C 0.4524(4) 0.38059(19) 0.85388(16) 0.0276(7) Uani 1 1 d . . . C14 C 0.5104(4) 0.31679(18) 0.80990(15) 0.0279(7) Uani 1 1 d . . . H14 H 0.4984 0.3236 0.7620 0.034 Uiso 1 1 calc R . . C15 C 0.5856(4) 0.24358(17) 0.83492(14) 0.0271(7) Uani 1 1 d . . . C16 C 0.6085(5) 0.23370(16) 0.90628(16) 0.0327(7) Uani 1 1 d . . . H16 H 0.6586 0.1847 0.9243 0.039 Uiso 1 1 calc R . . C17 C 0.5547(4) 0.2988(2) 0.94938(16) 0.0349(9) Uani 1 1 d . . . C18 C 0.4741(4) 0.3709(2) 0.92498(16) 0.0322(9) Uani 1 1 d . . . H18 H 0.4349 0.4123 0.9558 0.039 Uiso 1 1 calc R . . C19 C 0.3658(4) 0.46056(19) 0.82663(16) 0.0327(8) Uani 1 1 d . . . C20 C 0.6398(4) 0.1752(2) 0.78362(15) 0.0311(7) 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 Cs1 0.03294(10) 0.03332(9) 0.03008(8) -0.00192(10) 0.00158(12) 0.00264(10) O1 0.0370(17) 0.0536(16) 0.0458(15) -0.0153(13) -0.0043(14) -0.0022(12) O2 0.0476(15) 0.0370(13) 0.0689(16) 0.0010(15) 0.0038(18) 0.0102(10) O3 0.0517(19) 0.0734(17) 0.0377(14) 0.0199(14) 0.003(2) 0.0010(18) O4 0.0370(17) 0.0740(17) 0.0504(14) -0.0124(14) -0.0068(18) -0.0008(16) O5 0.0538(19) 0.0373(13) 0.0607(14) -0.0054(13) 0.0076(16) 0.0032(13) O6 0.0511(19) 0.0619(18) 0.0336(13) 0.0036(13) 0.0051(14) 0.0067(13) C1 0.061(3) 0.083(3) 0.0246(16) 0.005(2) -0.003(2) 0.022(2) C2 0.044(3) 0.093(3) 0.037(2) -0.026(2) -0.009(2) 0.013(2) C3 0.049(3) 0.055(3) 0.076(3) -0.039(2) 0.004(2) -0.0107(19) C4 0.055(3) 0.029(2) 0.112(4) -0.018(3) 0.022(3) -0.0028(19) C5 0.054(3) 0.043(3) 0.100(3) 0.030(3) 0.007(3) 0.0059(19) C6 0.061(3) 0.081(3) 0.065(3) 0.049(3) 0.011(2) 0.014(3) C7 0.059(3) 0.112(4) 0.0261(18) 0.006(2) -0.005(3) 0.023(3) C8 0.040(3) 0.107(4) 0.042(2) -0.020(2) -0.009(2) 0.010(3) C9 0.041(3) 0.070(3) 0.068(3) -0.041(3) 0.006(2) -0.016(2) C10 0.049(3) 0.039(2) 0.087(3) -0.028(2) 0.012(3) -0.009(2) C11 0.064(3) 0.037(2) 0.092(3) 0.022(2) 0.004(3) 0.007(2) C12 0.065(3) 0.060(3) 0.059(2) 0.026(2) 0.009(2) 0.007(2) O7 0.068(2) 0.0423(15) 0.0509(15) -0.0025(12) 0.0098(14) 0.0268(14) O8 0.066(2) 0.0276(12) 0.0373(12) 0.0045(10) -0.0106(15) 0.0045(12) O9 0.069(2) 0.0419(15) 0.0338(12) 0.0023(10) 0.0171(13) 0.0124(12) O10 0.066(2) 0.0257(12) 0.0338(12) -0.0010(10) -0.0048(13) 0.0041(11) O11 0.151(4) 0.0656(18) 0.0405(14) 0.0040(14) -0.022(2) 0.038(2) O12 0.203(4) 0.080(2) 0.0320(13) -0.0160(16) -0.0135(19) 0.059(2) N1 0.090(3) 0.0459(18) 0.0288(14) -0.0012(15) -0.009(2) 0.0128(19) C13 0.0293(19) 0.0216(16) 0.0319(16) 0.0003(14) -0.0011(16) -0.0044(13) C14 0.0315(19) 0.0243(18) 0.0280(15) 0.0012(14) -0.0020(15) -0.0036(13) C15 0.029(2) 0.0230(15) 0.0292(15) 0.0014(13) 0.0036(17) -0.0029(14) C16 0.0384(17) 0.0251(14) 0.0346(16) 0.0035(15) -0.008(3) 0.0000(16) C17 0.046(3) 0.0333(18) 0.0257(16) -0.0009(14) -0.0025(17) -0.0025(15) C18 0.040(2) 0.0250(17) 0.0314(17) -0.0070(14) 0.0019(16) 0.0026(15) C19 0.029(2) 0.0281(17) 0.0405(18) 0.0017(15) -0.0072(19) -0.0074(15) C20 0.029(2) 0.0319(18) 0.0327(15) -0.0029(16) -0.0001(15) -0.0012(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cs1 O7 2.991(2) . ? Cs1 O4 3.080(3) . ? Cs1 O9 3.080(2) 3_656 ? Cs1 O6 3.106(2) . ? Cs1 O2 3.109(2) . ? Cs1 O3 3.197(3) . ? Cs1 O1 3.276(2) . ? Cs1 O5 3.283(2) . ? Cs1 O1 3.412(2) 4_567 ? Cs1 C6 3.727(4) . ? Cs1 C7 3.776(4) . ? Cs1 C2 3.792(3) . ? O1 C2 1.417(4) . ? O1 C3 1.427(4) . ? O1 Cs1 3.412(2) 4_467 ? O2 C4 1.416(5) . ? O2 C5 1.430(5) . ? O3 C6 1.399(5) . ? O3 C7 1.432(4) . ? O4 C9 1.408(4) . ? O4 C8 1.422(5) . ? O5 C11 1.409(4) . ? O5 C10 1.425(4) . ? O6 C12 1.415(4) . ? O6 C1 1.423(4) . ? C1 C2 1.484(5) . ? C3 C4 1.487(6) . ? C5 C6 1.489(6) . ? C7 C8 1.462(5) . ? C9 C10 1.482(5) . ? C11 C12 1.490(5) . ? O7 C19 1.221(4) . ? O8 C19 1.272(3) . ? O9 C20 1.212(3) . ? O9 Cs1 3.080(2) 3_646 ? O10 C20 1.290(4) . ? O11 N1 1.204(4) . ? O12 N1 1.207(4) . ? N1 C17 1.478(4) . ? C13 C18 1.385(4) . ? C13 C14 1.385(4) . ? C13 C19 1.521(4) . ? C14 C15 1.377(4) . ? C15 C16 1.391(4) . ? C15 C20 1.514(4) . ? C16 C17 1.378(4) . ? C17 C18 1.380(4) . ? 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 O7 Cs1 O4 80.81(7) . . ? O7 Cs1 O9 67.22(6) . 3_656 ? O4 Cs1 O9 87.02(7) . 3_656 ? O7 Cs1 O6 91.54(7) . . ? O4 Cs1 O6 104.89(7) . . ? O9 Cs1 O6 153.99(7) 3_656 . ? O7 Cs1 O2 158.15(7) . . ? O4 Cs1 O2 106.13(7) . . ? O9 Cs1 O2 92.12(7) 3_656 . ? O6 Cs1 O2 106.15(7) . . ? O7 Cs1 O3 124.35(6) . . ? O4 Cs1 O3 54.29(6) . . ? O9 Cs1 O3 78.29(7) 3_656 . ? O6 Cs1 O3 127.48(7) . . ? O2 Cs1 O3 53.42(7) . . ? O7 Cs1 O1 139.54(7) . . ? O4 Cs1 O1 123.72(6) . . ? O9 Cs1 O1 136.94(6) 3_656 . ? O6 Cs1 O1 53.52(7) . . ? O2 Cs1 O1 53.32(7) . . ? O3 Cs1 O1 95.30(7) . . ? O7 Cs1 O5 74.43(7) . . ? O4 Cs1 O5 54.22(6) . . ? O9 Cs1 O5 129.15(6) 3_656 . ? O6 Cs1 O5 51.89(6) . . ? O2 Cs1 O5 126.65(7) . . ? O3 Cs1 O5 98.31(7) . . ? O1 Cs1 O5 93.85(6) . . ? O7 Cs1 O1 77.42(6) . 4_567 ? O4 Cs1 O1 153.87(6) . 4_567 ? O9 Cs1 O1 71.34(6) 3_656 4_567 ? O6 Cs1 O1 90.06(6) . 4_567 ? O2 Cs1 O1 89.58(7) . 4_567 ? O3 Cs1 O1 130.82(7) . 4_567 ? O1 Cs1 O1 82.41(3) . 4_567 ? O5 Cs1 O1 130.86(7) . 4_567 ? O7 Cs1 C6 129.45(8) . . ? O4 Cs1 C6 74.18(9) . . ? O9 Cs1 C6 68.27(8) 3_656 . ? O6 Cs1 C6 136.89(8) . . ? O2 Cs1 C6 39.25(9) . . ? O3 Cs1 C6 21.60(8) . . ? O1 Cs1 C6 90.25(9) . . ? O5 Cs1 C6 119.67(9) . . ? O1 Cs1 C6 109.36(8) 4_567 . ? O7 Cs1 C7 102.73(8) . . ? O4 Cs1 C7 38.55(8) . . ? O9 Cs1 C7 67.55(9) 3_656 . ? O6 Cs1 C7 134.78(9) . . ? O2 Cs1 C7 74.00(8) . . ? O3 Cs1 C7 21.72(7) . . ? O1 Cs1 C7 116.26(8) . . ? O5 Cs1 C7 90.75(9) . . ? O1 Cs1 C7 134.71(9) 4_567 . ? C6 Cs1 C7 36.79(10) . . ? O7 Cs1 C2 118.00(7) . . ? O4 Cs1 C2 133.13(8) . . ? O9 Cs1 C2 139.31(8) 3_656 . ? O6 Cs1 C2 38.63(8) . . ? O2 Cs1 C2 72.76(8) . . ? O3 Cs1 C2 116.72(8) . . ? O1 Cs1 C2 21.58(7) . . ? O5 Cs1 C2 87.95(7) . . ? O1 Cs1 C2 71.01(7) 4_567 . ? C6 Cs1 C2 111.14(9) . . ? C7 Cs1 C2 137.14(9) . . ? C2 O1 C3 111.2(3) . . ? C2 O1 Cs1 100.20(18) . . ? C3 O1 Cs1 102.72(19) . . ? C2 O1 Cs1 105.60(19) . 4_467 ? C3 O1 Cs1 103.1(2) . 4_467 ? Cs1 O1 Cs1 133.46(7) . 4_467 ? C4 O2 C5 113.0(3) . . ? C4 O2 Cs1 122.1(2) . . ? C5 O2 Cs1 120.0(2) . . ? C6 O3 C7 113.6(3) . . ? C6 O3 Cs1 101.1(2) . . ? C7 O3 Cs1 102.6(2) . . ? C9 O4 C8 113.0(3) . . ? C9 O4 Cs1 120.1(2) . . ? C8 O4 Cs1 119.9(2) . . ? C11 O5 C10 112.3(3) . . ? C11 O5 Cs1 100.4(2) . . ? C10 O5 Cs1 99.7(2) . . ? C12 O6 C1 112.7(3) . . ? C12 O6 Cs1 123.3(2) . . ? C1 O6 Cs1 121.0(2) . . ? O6 C1 C2 109.4(3) . . ? O1 C2 C1 110.4(3) . . ? O1 C2 Cs1 58.22(15) . . ? C1 C2 Cs1 88.2(2) . . ? O1 C3 C4 110.0(3) . . ? O1 C3 Cs1 56.08(15) . . ? C4 C3 Cs1 86.5(2) . . ? O2 C4 C3 109.2(3) . . ? O2 C5 C6 108.4(3) . . ? O3 C6 C5 110.0(3) . . ? O3 C6 Cs1 57.30(17) . . ? C5 C6 Cs1 90.2(2) . . ? O3 C7 C8 109.6(3) . . ? O3 C7 Cs1 55.70(17) . . ? C8 C7 Cs1 87.3(2) . . ? O4 C8 C7 109.6(3) . . ? O4 C9 C10 109.5(3) . . ? O5 C10 C9 109.0(3) . . ? O5 C10 Cs1 58.57(16) . . ? C9 C10 Cs1 86.2(2) . . ? O5 C11 C12 109.6(3) . . ? O5 C11 Cs1 58.16(18) . . ? C12 C11 Cs1 89.1(2) . . ? O6 C12 C11 108.1(3) . . ? C19 O7 Cs1 150.2(2) . . ? C20 O9 Cs1 140.9(2) . 3_646 ? O11 N1 O12 123.6(3) . . ? O11 N1 C17 118.5(3) . . ? O12 N1 C17 117.9(3) . . ? C18 C13 C14 118.6(3) . . ? C18 C13 C19 119.2(3) . . ? C14 C13 C19 122.2(3) . . ? C15 C14 C13 122.0(3) . . ? C14 C15 C16 119.6(3) . . ? C14 C15 C20 118.8(3) . . ? C16 C15 C20 121.6(3) . . ? C17 C16 C15 117.9(3) . . ? C16 C17 C18 122.9(3) . . ? C16 C17 N1 119.1(3) . . ? C18 C17 N1 118.0(3) . . ? C17 C18 C13 118.9(3) . . ? O7 C19 O8 126.7(3) . . ? O7 C19 C13 118.3(3) . . ? O8 C19 C13 115.0(3) . . ? O9 C20 O10 125.7(3) . . ? O9 C20 C15 119.5(3) . . ? O10 C20 C15 114.8(2) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.881 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.065 # Attachment '- 8-t-butyl-new.cif' data_seedtert(iso)_3 _database_code_depnum_ccdc_archive 'CCDC 794778' #TrackingRef '- 8-t-butyl-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CROWN ETHER COMPLEX' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H37 Cs O10' _chemical_formula_weight 618.45 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4406(3) _cell_length_b 16.2370(5) _cell_length_c 14.1394(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.318(2) _cell_angle_gamma 90.00 _cell_volume 2826.09(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3752 _cell_measurement_theta_min 2.3898 _cell_measurement_theta_max 25.5039 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.081 _exptl_crystal_size_min 0.078 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 1.359 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97276 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur S' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7825 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.95 _reflns_number_total 4775 _reflns_number_gt 2718 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -57.00 28.00 1.0000 35.8300 omega____ theta____ kappa____ phi______ frames - 9.1958 -38.0000 -60.0000 85 #__ type_ start__ end____ width___ exp.time_ 2 omega -76.00 -2.00 1.0000 35.8300 omega____ theta____ kappa____ phi______ frames - -9.5864 -38.0000 30.0000 74 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0534P)^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 rigid _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4775 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.003 _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 O1E O 0.2173(8) -0.0448(4) 0.9138(5) 0.147(2) Uani 1 1 d . . . O2E O 0.3698(5) 0.0041(4) 1.0668(6) 0.144(3) Uani 1 1 d . . . O3E O 0.2999(5) 0.1133(5) 1.1985(4) 0.1311(19) Uani 1 1 d . . . O4E O 0.1358(7) 0.2331(3) 1.1375(6) 0.153(2) Uani 1 1 d . . . O5E O -0.0162(5) 0.1733(5) 0.9983(8) 0.172(3) Uani 1 1 d . . . O6E O 0.0345(8) 0.0579(6) 0.8575(5) 0.166(3) Uani 1 1 d . . . C1E C 0.323(2) -0.0610(11) 0.9141(18) 0.294(19) Uani 1 1 d . . . H1E1 H 0.3577 -0.0156 0.8860 0.353 Uiso 1 1 calc R . . H1E2 H 0.3314 -0.1105 0.8775 0.353 Uiso 1 1 calc R . . C2E C 0.3700(11) -0.0723(9) 1.0127(18) 0.252(13) Uani 1 1 d . . . H2E1 H 0.4441 -0.0918 1.0154 0.302 Uiso 1 1 calc R . . H2E2 H 0.3292 -0.1139 1.0416 0.302 Uiso 1 1 calc R . . C3E C 0.3980(11) -0.0078(11) 1.1567(17) 0.248(12) Uani 1 1 d . . . H3E1 H 0.4670 -0.0366 1.1687 0.298 Uiso 1 1 calc R . . H3E2 H 0.3436 -0.0399 1.1830 0.298 Uiso 1 1 calc R . . C4E C 0.4076(8) 0.0771(11) 1.2001(7) 0.188(7) Uani 1 1 d . . . H4E1 H 0.4439 0.0738 1.2655 0.225 Uiso 1 1 calc R . . H4E2 H 0.4510 0.1117 1.1644 0.225 Uiso 1 1 calc R . . C5E C 0.2992(15) 0.1911(12) 1.2339(10) 0.231(9) Uani 1 1 d . . . H5E1 H 0.3365 0.2282 1.1958 0.277 Uiso 1 1 calc R . . H5E2 H 0.3363 0.1924 1.2992 0.277 Uiso 1 1 calc R . . C6E C 0.1809(18) 0.2184(9) 1.2311(11) 0.220(10) Uani 1 1 d . . . H6E1 H 0.1401 0.1757 1.2582 0.265 Uiso 1 1 calc R . . H6E2 H 0.1778 0.2681 1.2687 0.265 Uiso 1 1 calc R . . C7E C 0.0265(12) 0.2536(8) 1.1292(14) 0.225(10) Uani 1 1 d . . . H7E1 H 0.0193 0.3081 1.1555 0.269 Uiso 1 1 calc R . . H7E2 H -0.0101 0.2150 1.1662 0.269 Uiso 1 1 calc R . . C8E C -0.0264(12) 0.2521(13) 1.0284(17) 0.265(14) Uani 1 1 d . . . H8E1 H -0.1024 0.2673 1.0239 0.318 Uiso 1 1 calc R . . H8E2 H 0.0093 0.2901 0.9901 0.318 Uiso 1 1 calc R . . C9E C -0.0766(13) 0.1595(13) 0.9093(14) 0.244(11) Uani 1 1 d . . . H9E1 H -0.0501 0.1952 0.8628 0.293 Uiso 1 1 calc R . . H9E2 H -0.1518 0.1740 0.9119 0.293 Uiso 1 1 calc R . . C10E C -0.0718(13) 0.0756(12) 0.8781(12) 0.243(11) Uani 1 1 d . . . H10A H -0.0894 0.0388 0.9277 0.292 Uiso 1 1 calc R . . H10B H -0.1245 0.0669 0.8213 0.292 Uiso 1 1 calc R . . C11E C 0.0431(17) -0.0209(13) 0.8231(10) 0.236(11) Uani 1 1 d . . . H11A H 0.0010 -0.0256 0.7600 0.283 Uiso 1 1 calc R . . H11B H 0.0145 -0.0600 0.8650 0.283 Uiso 1 1 calc R . . C12E C 0.159(2) -0.0396(9) 0.8182(12) 0.229(11) Uani 1 1 d . . . H12A H 0.1642 -0.0914 0.7851 0.275 Uiso 1 1 calc R . . H12B H 0.1896 0.0034 0.7829 0.275 Uiso 1 1 calc R . . O1 O 0.4540(3) 0.2273(3) 1.0233(3) 0.1016(15) Uani 1 1 d . . . O2 O 0.4786(4) 0.2933(4) 0.8898(3) 0.140(2) Uani 1 1 d . . . H2O H 0.4594 0.2516 0.8595 0.210 Uiso 1 1 calc R . . O3 O 0.7698(7) 0.2416(3) 1.2892(4) 0.168(3) Uani 1 1 d . . . O4 O 0.8749(4) 0.3485(4) 1.2972(3) 0.128(2) Uani 1 1 d . . . C1 C 0.5971(4) 0.3233(3) 1.0300(3) 0.0528(13) Uani 1 1 d . . . C2 C 0.6336(3) 0.3941(3) 0.9906(3) 0.0517(12) Uani 1 1 d . . . H2 H 0.5990 0.4119 0.9315 0.062 Uiso 1 1 calc R . . C3 C 0.7201(3) 0.4394(3) 1.0368(3) 0.0488(12) Uani 1 1 d . . . C4 C 0.7701(3) 0.4077(3) 1.1230(3) 0.0510(13) Uani 1 1 d . . . H4 H 0.8298 0.4357 1.1550 0.061 Uiso 1 1 calc R . . C5 C 0.7368(4) 0.3379(3) 1.1636(3) 0.0519(13) Uani 1 1 d . . . C6 C 0.6494(4) 0.2962(3) 1.1173(4) 0.0606(14) Uani 1 1 d . . . H6 H 0.6248 0.2491 1.1449 0.073 Uiso 1 1 calc R . . C7 C 0.5031(5) 0.2750(4) 0.9801(4) 0.0817(18) Uani 1 1 d . . . C8 C 0.8016(6) 0.3046(5) 1.2587(4) 0.084(2) Uani 1 1 d . . . C9 C 0.7576(5) 0.5186(4) 0.9943(4) 0.0740(17) Uani 1 1 d . . . C10 C 0.6721(11) 0.5581(7) 0.9316(11) 0.306(11) Uani 1 1 d . . . H10C H 0.6150 0.5736 0.9670 0.459 Uiso 1 1 calc R . . H10D H 0.6439 0.5208 0.8814 0.459 Uiso 1 1 calc R . . H10E H 0.7001 0.6063 0.9044 0.459 Uiso 1 1 calc R . . C11 C 0.8004(10) 0.5791(5) 1.0661(6) 0.187(5) Uani 1 1 d . . . H11C H 0.8579 0.5547 1.1098 0.280 Uiso 1 1 calc R . . H11D H 0.7435 0.5969 1.1005 0.280 Uiso 1 1 calc R . . H11E H 0.8281 0.6256 1.0353 0.280 Uiso 1 1 calc R . . C12 C 0.8423(13) 0.4993(6) 0.9379(11) 0.299(11) Uani 1 1 d . . . H12C H 0.9018 0.4734 0.9778 0.449 Uiso 1 1 calc R . . H12D H 0.8670 0.5490 0.9114 0.449 Uiso 1 1 calc R . . H12E H 0.8143 0.4625 0.8871 0.449 Uiso 1 1 calc R . . Cs1 Cs 0.23176(2) 0.14595(2) 0.97526(2) 0.06508(16) 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 O1E 0.210(6) 0.108(4) 0.150(6) -0.039(4) 0.116(5) -0.056(4) O2E 0.108(4) 0.117(5) 0.220(7) 0.075(5) 0.069(4) 0.030(4) O3E 0.144(5) 0.168(6) 0.076(4) 0.019(4) -0.001(3) -0.048(5) O4E 0.204(7) 0.097(4) 0.186(7) -0.032(4) 0.127(6) -0.012(4) O5E 0.086(4) 0.127(6) 0.304(11) 0.084(6) 0.033(5) 0.014(4) O6E 0.200(8) 0.169(7) 0.109(5) 0.033(5) -0.042(4) -0.103(6) C1E 0.39(3) 0.121(13) 0.46(4) -0.14(2) 0.35(3) -0.084(17) C2E 0.151(10) 0.081(8) 0.57(4) -0.012(18) 0.22(2) 0.025(7) C3E 0.111(8) 0.231(18) 0.42(3) 0.23(2) 0.095(13) 0.068(10) C4E 0.090(6) 0.34(2) 0.116(8) 0.125(12) -0.038(5) -0.039(10) C5E 0.32(2) 0.26(2) 0.102(9) -0.052(10) 0.001(12) -0.13(2) C6E 0.42(3) 0.137(10) 0.135(11) -0.080(9) 0.160(17) -0.099(16) C7E 0.194(14) 0.080(7) 0.46(3) -0.004(13) 0.239(18) 0.020(9) C8E 0.117(10) 0.156(13) 0.54(4) 0.15(2) 0.096(16) 0.059(10) C9E 0.122(9) 0.28(2) 0.31(2) 0.17(2) -0.050(11) 0.019(14) C10E 0.138(10) 0.26(2) 0.288(18) 0.135(19) -0.113(11) -0.093(15) C11E 0.34(3) 0.231(18) 0.101(10) 0.020(11) -0.082(13) -0.15(2) C12E 0.46(3) 0.136(11) 0.112(11) -0.039(9) 0.126(16) -0.142(19) O1 0.114(3) 0.124(4) 0.068(3) -0.011(3) 0.015(2) -0.072(3) O2 0.137(4) 0.236(6) 0.041(3) -0.009(3) -0.004(2) -0.125(4) O3 0.346(10) 0.072(3) 0.064(3) 0.012(3) -0.042(4) 0.027(5) O4 0.080(3) 0.232(7) 0.061(3) 0.004(4) -0.025(2) 0.008(4) C1 0.060(3) 0.060(3) 0.037(3) -0.005(3) 0.002(2) -0.017(3) C2 0.050(3) 0.067(3) 0.035(3) 0.001(3) -0.006(2) -0.007(3) C3 0.045(2) 0.054(3) 0.048(3) -0.007(3) 0.010(2) -0.001(3) C4 0.034(2) 0.065(4) 0.050(3) -0.021(3) -0.009(2) 0.001(2) C5 0.064(3) 0.051(4) 0.038(3) -0.005(3) -0.002(2) 0.021(3) C6 0.094(4) 0.043(3) 0.043(3) 0.000(3) 0.005(3) -0.006(3) C7 0.088(4) 0.107(5) 0.050(4) -0.011(4) 0.008(3) -0.048(4) C8 0.107(5) 0.106(6) 0.037(4) -0.017(4) 0.000(4) 0.037(5) C9 0.087(4) 0.058(4) 0.078(4) -0.007(3) 0.014(3) -0.026(3) C10 0.266(14) 0.164(10) 0.43(2) 0.211(14) -0.148(16) -0.089(11) C11 0.352(14) 0.093(6) 0.117(7) -0.017(5) 0.041(8) -0.106(8) C12 0.47(2) 0.117(8) 0.40(2) -0.025(10) 0.38(2) -0.089(12) Cs1 0.0580(2) 0.0723(3) 0.0667(3) -0.0015(2) 0.01490(15) -0.01183(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 O1E C1E 1.34(2) . ? O1E C12E 1.443(19) . ? O1E Cs1 3.215(6) . ? O2E C3E 1.28(2) . ? O2E C2E 1.458(18) . ? O2E Cs1 3.047(6) . ? O3E C5E 1.361(16) . ? O3E C4E 1.460(13) . ? O3E Cs1 3.192(5) . ? O4E C6E 1.381(17) . ? O4E C7E 1.389(14) . ? O4E Cs1 3.079(6) . ? O5E C8E 1.36(2) . ? O5E C9E 1.387(18) . ? O5E Cs1 3.179(6) . ? O6E C11E 1.38(2) . ? O6E C10E 1.424(19) . ? O6E Cs1 3.107(6) . ? C1E C2E 1.44(3) . ? C1E Cs1 3.688(16) . ? C3E C4E 1.51(2) . ? C4E Cs1 3.759(8) . ? C5E C6E 1.53(2) . ? C5E Cs1 3.705(13) . ? C7E C8E 1.48(2) . ? C8E Cs1 3.814(15) . ? C9E C10E 1.44(2) . ? C9E Cs1 3.821(15) . ? C11E C12E 1.48(2) . ? C12E Cs1 3.775(14) . ? O1 C7 1.206(6) . ? O1 Cs1 3.051(4) . ? O2 C7 1.303(7) . ? O3 C8 1.200(9) . ? O3 Cs1 3.293(6) 4_666 ? O4 C8 1.221(8) . ? O4 Cs1 3.289(5) 4_666 ? C1 C6 1.382(6) . ? C1 C2 1.382(7) . ? C1 C7 1.497(7) . ? C2 C3 1.386(6) . ? C3 C4 1.385(6) . ? C3 C9 1.521(7) . ? C4 C5 1.362(7) . ? C5 C6 1.364(7) . ? C5 C8 1.561(8) . ? C8 Cs1 3.398(6) 4_666 ? C9 C10 1.434(11) . ? C9 C12 1.445(11) . ? C9 C11 1.458(9) . ? Cs1 O4 3.289(5) 4_565 ? Cs1 O3 3.293(6) 4_565 ? Cs1 C8 3.398(6) 4_565 ? 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 C1E O1E C12E 112.2(11) . . ? C1E O1E Cs1 99.9(8) . . ? C12E O1E Cs1 101.4(7) . . ? C3E O2E C2E 111.8(12) . . ? C3E O2E Cs1 126.2(10) . . ? C2E O2E Cs1 117.7(10) . . ? C5E O3E C4E 115.0(10) . . ? C5E O3E Cs1 101.2(7) . . ? C4E O3E Cs1 101.2(5) . . ? C6E O4E C7E 112.3(10) . . ? C6E O4E Cs1 119.2(8) . . ? C7E O4E Cs1 121.9(9) . . ? C8E O5E C9E 111.9(12) . . ? C8E O5E Cs1 107.4(7) . . ? C9E O5E Cs1 106.9(9) . . ? C11E O6E C10E 112.3(11) . . ? C11E O6E Cs1 121.4(10) . . ? C10E O6E Cs1 118.9(10) . . ? O1E C1E C2E 106.9(14) . . ? O1E C1E Cs1 59.1(7) . . ? C2E C1E Cs1 89.2(10) . . ? C1E C2E O2E 111.5(15) . . ? O2E C3E C4E 105.1(10) . . ? O3E C4E C3E 110.1(9) . . ? O3E C4E Cs1 56.4(3) . . ? C3E C4E Cs1 85.7(8) . . ? O3E C5E C6E 108.4(12) . . ? O3E C5E Cs1 57.7(5) . . ? C6E C5E Cs1 87.2(9) . . ? O4E C6E C5E 109.3(11) . . ? O4E C7E C8E 111.7(13) . . ? O5E C8E C7E 105.5(15) . . ? O5E C8E Cs1 52.7(6) . . ? C7E C8E Cs1 85.9(8) . . ? O5E C9E C10E 113.0(13) . . ? O5E C9E Cs1 52.7(7) . . ? C10E C9E Cs1 86.3(10) . . ? O6E C10E C9E 109.6(15) . . ? O6E C11E C12E 109.3(15) . . ? O1E C12E C11E 109.4(12) . . ? O1E C12E Cs1 56.6(5) . . ? C11E C12E Cs1 87.8(11) . . ? C7 O1 Cs1 132.4(4) . . ? C8 O3 Cs1 84.7(4) . 4_666 ? C8 O4 Cs1 84.6(4) . 4_666 ? C6 C1 C2 119.0(4) . . ? C6 C1 C7 119.3(5) . . ? C2 C1 C7 121.7(5) . . ? C1 C2 C3 122.0(4) . . ? C2 C3 C4 115.9(5) . . ? C2 C3 C9 121.6(4) . . ? C4 C3 C9 122.5(4) . . ? C5 C4 C3 123.6(4) . . ? C4 C5 C6 118.8(4) . . ? C4 C5 C8 120.0(6) . . ? C6 C5 C8 121.2(6) . . ? C5 C6 C1 120.7(5) . . ? O1 C7 O2 125.4(5) . . ? O1 C7 C1 121.1(5) . . ? O2 C7 C1 113.5(5) . . ? O3 C8 O4 126.9(7) . . ? O3 C8 C5 116.7(7) . . ? O4 C8 C5 116.2(7) . . ? O3 C8 Cs1 74.7(4) . 4_666 ? O4 C8 Cs1 74.5(3) . 4_666 ? C5 C8 Cs1 121.8(3) . 4_666 ? C10 C9 C12 106.9(10) . . ? C10 C9 C11 107.0(9) . . ? C12 C9 C11 108.0(8) . . ? C10 C9 C3 112.4(6) . . ? C12 C9 C3 108.9(6) . . ? C11 C9 C3 113.4(5) . . ? O2E Cs1 O1 78.22(15) . . ? O2E Cs1 O4E 106.6(2) . . ? O1 Cs1 O4E 94.12(17) . . ? O2E Cs1 O6E 103.5(2) . . ? O1 Cs1 O6E 159.8(2) . . ? O4E Cs1 O6E 104.4(3) . . ? O2E Cs1 O5E 123.88(16) . . ? O1 Cs1 O5E 141.1(2) . . ? O4E Cs1 O5E 51.2(3) . . ? O6E Cs1 O5E 54.3(3) . . ? O2E Cs1 O3E 53.2(2) . . ? O1 Cs1 O3E 75.48(13) . . ? O4E Cs1 O3E 54.2(2) . . ? O6E Cs1 O3E 121.99(15) . . ? O5E Cs1 O3E 92.6(2) . . ? O2E Cs1 O1E 52.6(2) . . ? O1 Cs1 O1E 119.38(19) . . ? O4E Cs1 O1E 129.16(14) . . ? O6E Cs1 O1E 53.3(3) . . ? O5E Cs1 O1E 98.3(2) . . ? O3E Cs1 O1E 96.0(2) . . ? O2E Cs1 O4 90.69(17) . 4_565 ? O1 Cs1 O4 65.48(11) . 4_565 ? O4E Cs1 O4 150.34(15) . 4_565 ? O6E Cs1 O4 94.31(19) . 4_565 ? O5E Cs1 O4 135.7(2) . 4_565 ? O3E Cs1 O4 131.76(15) . 4_565 ? O1E Cs1 O4 80.49(15) . 4_565 ? O2E Cs1 O3 128.41(19) . 4_565 ? O1 Cs1 O3 72.98(15) . 4_565 ? O4E Cs1 O3 117.18(19) . 4_565 ? O6E Cs1 O3 91.17(15) . 4_565 ? O5E Cs1 O3 105.0(2) . 4_565 ? O3E Cs1 O3 146.51(14) . 4_565 ? O1E Cs1 O3 109.09(16) . 4_565 ? O4 Cs1 O3 38.42(17) 4_565 4_565 ? O2E Cs1 C8 111.1(2) . 4_565 ? O1 Cs1 C8 75.91(13) . 4_565 ? O4E Cs1 C8 137.8(2) . 4_565 ? O6E Cs1 C8 84.87(17) . 4_565 ? O5E Cs1 C8 115.9(2) . 4_565 ? O3E Cs1 C8 149.82(16) . 4_565 ? O1E Cs1 C8 89.74(18) . 4_565 ? O4 Cs1 C8 20.95(14) 4_565 4_565 ? O3 Cs1 C8 20.58(15) 4_565 4_565 ? O2E Cs1 C1E 40.4(5) . . ? O1 Cs1 C1E 98.5(4) . . ? O4E Cs1 C1E 139.3(3) . . ? O6E Cs1 C1E 72.6(5) . . ? O5E Cs1 C1E 119.1(4) . . ? O3E Cs1 C1E 91.9(5) . . ? O1E Cs1 C1E 20.9(4) . . ? O4 Cs1 C1E 68.1(3) 4_565 . ? O3 Cs1 C1E 103.5(3) 4_565 . ? C8 Cs1 C1E 82.9(4) 4_565 . ? O2E Cs1 C5E 72.4(4) . . ? O1 Cs1 C5E 68.0(3) . . ? O4E Cs1 C5E 39.7(4) . . ? O6E Cs1 C5E 132.0(3) . . ? O5E Cs1 C5E 87.5(4) . . ? O3E Cs1 C5E 21.1(3) . . ? O1E Cs1 C5E 117.0(3) . . ? O4 Cs1 C5E 132.8(3) 4_565 . ? O3 Cs1 C5E 129.8(3) 4_565 . ? C8 Cs1 C5E 142.4(3) 4_565 . ? C1E Cs1 C5E 112.2(6) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.434 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.061