# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Stefano Di Stefano' _publ_contact_author_email stefano.distefano@uniroma1.it _publ_section_title ; Highly Efficient Intramolecular Cannizzaro Reaction between 1,3-Distal Formyl Groups at the Upper Rim of a cone Calix[4]arene ; loop_ _publ_author_name 'S.Di Stefano' J.Berrocal Mandolini R.Cacciapaglia A.Casnati ; L.Baldini ; F.Ugozzoli M.Galli # Attachment '- cif_compound_5.cif' data_roma2011 _database_code_depnum_ccdc_archive 'CCDC 836028' #TrackingRef '- cif_compound_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H58 O11' _chemical_formula_weight 786.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.266(8) _cell_length_b 13.805(4) _cell_length_c 12.483(3) _cell_angle_alpha 73.773(14) _cell_angle_beta 69.52(3) _cell_angle_gamma 71.78(3) _cell_volume 2147.3(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 11 _cell_measurement_theta_max 30 _exptl_crystal_description 'thick column' _exptl_crystal_colour transparent _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 1.11 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens AED' _diffrn_measurement_method 1KeV _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8094 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 69.89 _reflns_number_total 8094 _reflns_number_gt 5060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DIPCHIGE sofware package 2004' _computing_cell_refinement 'DIPCHIGE software package 2004' _computing_data_reduction DIFAU92 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Accelrys DS-ViewerPro 2005' _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^)+(0.1957P)^2^+0.1090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8094 _refine_ls_number_parameters 665 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1216 _refine_ls_R_factor_gt 0.0894 _refine_ls_wR_factor_ref 0.2914 _refine_ls_wR_factor_gt 0.2518 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.013 _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 C1A C 0.5233(2) 0.2317(3) 0.6415(3) 0.0564(7) Uani 1 1 d . . . C1B C 0.3043(2) 0.3449(2) 0.4962(2) 0.0524(7) Uani 1 1 d . . . C1C C 0.0940(3) 0.2681(3) 0.7812(3) 0.0579(8) Uani 1 1 d . . . C1D C 0.3183(3) 0.1231(3) 0.9126(3) 0.0575(8) Uani 1 1 d . . . C2A C 0.5632(2) 0.2459(2) 0.5196(3) 0.0534(7) Uani 1 1 d . . . C2B C 0.2184(3) 0.3066(3) 0.5179(3) 0.0555(7) Uani 1 1 d . . . C2C C 0.0680(3) 0.1859(3) 0.8713(3) 0.0604(8) Uani 1 1 d . . . C2D C 0.4201(3) 0.0767(3) 0.8558(3) 0.0601(8) Uani 1 1 d . . . C3A C 0.6572(3) 0.1815(3) 0.4728(3) 0.0591(8) Uani 1 1 d . . . C3B C 0.2359(3) 0.2085(3) 0.4940(3) 0.0682(9) Uani 1 1 d . . . C3C C 0.0006(3) 0.1352(3) 0.8653(3) 0.0620(8) Uani 1 1 d . . . C3D C 0.4354(3) -0.0068(3) 0.8053(3) 0.0707(9) Uani 1 1 d . . . C4A C 0.7096(3) 0.1040(3) 0.5433(3) 0.0578(8) Uani 1 1 d . . . C4B C 0.3345(3) 0.1510(3) 0.4518(4) 0.0746(10) Uani 1 1 d . . . C4C C -0.0403(3) 0.1625(3) 0.7716(3) 0.0611(8) Uani 1 1 d . . . C4D C 0.3546(4) -0.0438(3) 0.8109(4) 0.0804(11) Uani 1 1 d . . . C5A C 0.6629(3) 0.0858(3) 0.6642(3) 0.0588(8) Uani 1 1 d . . . C5B C 0.4183(3) 0.1889(3) 0.4344(3) 0.0672(9) Uani 1 1 d . . . C5C C -0.0079(3) 0.2411(3) 0.6797(3) 0.0599(8) Uani 1 1 d . . . C5D C 0.2545(4) 0.0063(3) 0.8626(4) 0.0747(10) Uani 1 1 d . . . C6A C 0.5682(3) 0.1462(3) 0.7149(3) 0.0574(7) Uani 1 1 d . . . C6B C 0.4045(2) 0.2869(3) 0.4566(3) 0.0549(7) Uani 1 1 d . . . C6C C 0.0602(3) 0.2933(3) 0.6815(3) 0.0588(8) Uani 1 1 d . . . C6D C 0.2340(3) 0.0901(3) 0.9157(3) 0.0610(8) Uani 1 1 d . . . C7A C 0.4461(4) 0.3995(3) 0.6861(4) 0.0752(10) Uani 1 1 d . . . C7B C 0.2684(3) 0.5257(3) 0.4259(3) 0.0631(8) Uani 1 1 d . . . C7C C 0.1119(4) 0.4176(4) 0.8205(7) 0.1137(19) Uani 1 1 d . . . H7C1 H 0.0906 0.4659 0.7565 0.136 Uiso 1 1 calc R . . H7C2 H 0.0510 0.4109 0.8841 0.136 Uiso 1 1 calc R . . C7D C 0.2990(4) 0.1714(4) 1.0874(3) 0.0823(12) Uani 1 1 d . . . C8A C 0.4552(4) 0.4082(4) 0.7992(4) 0.0794(11) Uani 1 1 d . . . C8B C 0.2365(3) 0.6271(3) 0.4672(4) 0.0707(10) Uani 1 1 d . . . C8C C 0.1673(9) 0.4564(6) 0.8514(11) 0.231(7) Uani 1 1 d . . . H8C1 H 0.2297 0.4592 0.7888 0.277 Uiso 1 1 calc R . . H8C2 H 0.1863 0.4086 0.9170 0.277 Uiso 1 1 calc R . . C8D C 0.2615(6) 0.2622(7) 1.1456(4) 0.136(3) Uani 1 1 d . . . H8D1 H 0.1908 0.2926 1.1469 0.163 Uiso 1 1 calc R . . H8D2 H 0.2630 0.2374 1.2251 0.163 Uiso 1 1 calc R . . C9A C 0.5661(4) 0.3475(5) 0.9179(5) 0.1041(16) Uani 1 1 d . . . H9A1 H 0.5117 0.3223 0.9799 0.125 Uiso 1 1 calc R . . H9A2 H 0.5627 0.4161 0.9249 0.125 Uiso 1 1 calc R . . C9B C 0.0999(3) 0.7310(3) 0.5874(4) 0.0737(10) Uani 1 1 d . . . C9C C 0.1991(5) 0.6114(5) 0.8531(5) 0.1133(18) Uani 1 1 d . . . H9C1 H 0.2327 0.6198 0.7708 0.136 Uiso 1 1 calc R . . H9C2 H 0.2502 0.5736 0.8929 0.136 Uiso 1 1 calc R . . C9D C 0.2829(7) 0.4135(7) 1.1678(6) 0.146(3) Uani 1 1 d . . . H9D1 H 0.3334 0.4542 1.1349 0.175 Uiso 1 1 calc R . . H9D2 H 0.2876 0.3792 1.2447 0.175 Uiso 1 1 calc R . . C10A C 0.6676(6) 0.2776(6) 0.9260(7) 0.141(2) Uani 1 1 d . . . H10A H 0.6709 0.2094 0.9178 0.169 Uiso 1 1 calc R . . H10B H 0.6757 0.2738 1.0004 0.169 Uiso 1 1 calc R . . H10C H 0.7218 0.3043 0.8652 0.169 Uiso 1 1 calc R . . C10B C -0.0052(4) 0.7342(4) 0.6708(5) 0.0897(13) Uani 1 1 d . . . C10C C 0.1519(5) 0.7142(4) 0.8857(5) 0.1104(17) Uani 1 1 d . . . H10D H 0.1002 0.7516 0.8466 0.132 Uiso 1 1 calc R . . H10E H 0.2039 0.7522 0.8634 0.132 Uiso 1 1 calc R . . H10F H 0.1207 0.7057 0.9685 0.132 Uiso 1 1 calc R . . C10D C 0.1795(8) 0.4865(6) 1.1799(7) 0.154(3) Uani 1 1 d . . . H10G H 0.1637 0.5051 1.1070 0.185 Uiso 1 1 calc R . . H10H H 0.1795 0.5479 1.2017 0.185 Uiso 1 1 calc R . . H10I H 0.1285 0.4536 1.2389 0.185 Uiso 1 1 calc R . . C11A C 0.8139(3) 0.0397(3) 0.4959(3) 0.0608(8) Uani 1 1 d . . . C11C C -0.1083(3) 0.1026(3) 0.7639(4) 0.0652(9) Uani 1 1 d . . . C20A C 0.4991(3) 0.3235(3) 0.4426(3) 0.0593(8) Uani 1 1 d . . . C20B C 0.1089(3) 0.3650(3) 0.5726(3) 0.0606(8) Uani 1 1 d . . . C20C C 0.1229(3) 0.1475(3) 0.9654(3) 0.0648(9) Uani 1 1 d . . . C20D C 0.5100(3) 0.1204(3) 0.8425(3) 0.0623(8) Uani 1 1 d . . . O1A O 0.43386(18) 0.29800(19) 0.6911(2) 0.0652(6) Uani 1 1 d . . . O1B O 0.28947(17) 0.44247(16) 0.51988(18) 0.0562(5) Uani 1 1 d . . . O1C O 0.16075(18) 0.31855(18) 0.7866(2) 0.0635(6) Uani 1 1 d . . . O1D O 0.30031(19) 0.20459(18) 0.96745(18) 0.0628(6) Uani 1 1 d . . . O2A O 0.5543(2) 0.3506(2) 0.8090(2) 0.0780(7) Uani 1 1 d . . . O2B O 0.13544(19) 0.63775(19) 0.5431(2) 0.0688(6) Uani 1 1 d . . . O2C O 0.1256(3) 0.5559(3) 0.8815(4) 0.1153(13) Uani 1 1 d . . . O2D O 0.3116(4) 0.3351(4) 1.0998(4) 0.1450(18) Uani 1 1 d . . . O3A O 0.8676(2) -0.0185(2) 0.5560(3) 0.0792(7) Uani 1 1 d . . . O3C O -0.0474(2) 0.0165(2) 0.7089(3) 0.0832(8) Uani 1 1 d . . . O4A O 0.8438(2) 0.0518(2) 0.3808(2) 0.0768(7) Uani 1 1 d . . . H2C H -0.014(3) 0.084(3) 0.922(4) 0.065(10) Uiso 1 1 d . . . H2A H 0.700(3) 0.032(3) 0.716(3) 0.064(10) Uiso 1 1 d . . . H16B H 0.109(3) 0.432(3) 0.596(3) 0.066(10) Uiso 1 1 d . . . H17B H 0.076(3) 0.382(3) 0.515(4) 0.079(12) Uiso 1 1 d . . . H16A H 0.480(3) 0.390(3) 0.461(3) 0.067(10) Uiso 1 1 d . . . H1C H -0.034(3) 0.264(3) 0.611(3) 0.054(9) Uiso 1 1 d . . . H1B H 0.175(3) 0.184(3) 0.505(3) 0.062(10) Uiso 1 1 d . . . H16D H 0.558(3) 0.072(3) 0.885(3) 0.066(10) Uiso 1 1 d . . . H4B H 0.211(3) 0.519(2) 0.404(3) 0.050(8) Uiso 1 1 d . . . H16C H 0.128(3) 0.199(3) 0.996(3) 0.069(11) Uiso 1 1 d . . . H17D H 0.483(3) 0.182(3) 0.878(3) 0.060(9) Uiso 1 1 d . . . H3B H 0.491(3) 0.147(3) 0.406(4) 0.082(12) Uiso 1 1 d . . . H17A H 0.544(3) 0.324(3) 0.357(3) 0.062(10) Uiso 1 1 d . . . H15C H 0.089(3) 0.097(3) 1.023(4) 0.085(13) Uiso 1 1 d . . . H6B H 0.283(4) 0.631(3) 0.506(4) 0.087(14) Uiso 1 1 d . . . H2D H 0.370(4) -0.103(4) 0.768(4) 0.103(15) Uiso 1 1 d . . . H3D H 0.195(4) -0.023(4) 0.872(4) 0.100(15) Uiso 1 1 d . . . H7B H 0.234(3) 0.687(3) 0.390(4) 0.079(12) Uiso 1 1 d . . . H1D H 0.507(3) -0.045(3) 0.762(4) 0.077(11) Uiso 1 1 d . . . H2B H 0.345(3) 0.083(4) 0.434(4) 0.086(12) Uiso 1 1 d . . . H1A H 0.687(3) 0.193(3) 0.382(4) 0.080(12) Uiso 1 1 d . . . H13C H -0.169(4) 0.136(4) 0.737(4) 0.092(14) Uiso 1 1 d . . . H5B H 0.330(3) 0.520(3) 0.365(4) 0.067(10) Uiso 1 1 d . . . H12C H -0.148(3) 0.076(3) 0.837(4) 0.070(11) Uiso 1 1 d . . . H7A H 0.404(4) 0.382(4) 0.869(5) 0.093(14) Uiso 1 1 d . . . H6A H 0.445(4) 0.483(4) 0.797(4) 0.102(15) Uiso 1 1 d . . . H6D H 0.246(4) 0.125(4) 1.127(4) 0.096(15) Uiso 1 1 d . . . H22A H 0.147(4) 0.738(3) 0.623(4) 0.087(13) Uiso 1 1 d . . . H9A H 0.099(3) 0.796(4) 0.521(4) 0.084(12) Uiso 1 1 d . . . H4A H 0.503(4) 0.419(4) 0.614(5) 0.112(17) Uiso 1 1 d . . . H5D H 0.380(5) 0.131(5) 1.090(5) 0.13(2) Uiso 1 1 d . . . H11A H -0.002(3) 0.682(4) 0.740(4) 0.087(14) Uiso 1 1 d . . . H13A H -0.055(4) 0.732(4) 0.639(5) 0.099(16) Uiso 1 1 d . . . H5A H 0.380(4) 0.457(4) 0.670(4) 0.104(15) Uiso 1 1 d . . . H12A H -0.036(4) 0.801(5) 0.706(5) 0.116(18) Uiso 1 1 d . . . H20A H 0.917(5) 0.023(4) 0.348(5) 0.112(17) Uiso 1 1 d . . . H20C H -0.087(4) -0.002(4) 0.678(5) 0.116(19) 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 C1A 0.0546(17) 0.0603(18) 0.0554(17) -0.0131(14) -0.0131(14) -0.0164(14) C1B 0.0636(18) 0.0530(16) 0.0393(14) -0.0069(12) -0.0131(13) -0.0157(14) C1C 0.0580(18) 0.0596(18) 0.0539(17) -0.0146(14) -0.0093(14) -0.0154(14) C1D 0.069(2) 0.0556(17) 0.0430(15) -0.0057(13) -0.0125(14) -0.0161(15) C2A 0.0564(17) 0.0527(16) 0.0510(16) -0.0091(13) -0.0121(13) -0.0177(13) C2B 0.0628(18) 0.0561(17) 0.0452(15) -0.0038(13) -0.0147(13) -0.0170(14) C2C 0.0610(18) 0.0641(19) 0.0497(17) -0.0127(14) -0.0075(14) -0.0141(15) C2D 0.068(2) 0.0588(18) 0.0507(17) -0.0059(14) -0.0148(15) -0.0179(15) C3A 0.0617(19) 0.0622(19) 0.0558(18) -0.0160(15) -0.0095(15) -0.0222(15) C3B 0.072(2) 0.067(2) 0.073(2) -0.0198(17) -0.0156(18) -0.0261(18) C3C 0.065(2) 0.0605(19) 0.0536(18) -0.0031(15) -0.0096(15) -0.0210(16) C3D 0.073(2) 0.066(2) 0.067(2) -0.0203(18) -0.0090(18) -0.0157(18) C4A 0.0590(18) 0.0545(17) 0.0638(19) -0.0154(15) -0.0168(15) -0.0160(14) C4B 0.083(3) 0.066(2) 0.081(3) -0.0324(19) -0.013(2) -0.0199(19) C4C 0.0563(18) 0.0651(19) 0.0574(18) -0.0149(15) -0.0073(14) -0.0157(15) C4D 0.088(3) 0.071(2) 0.083(3) -0.031(2) -0.006(2) -0.027(2) C5A 0.0620(19) 0.0544(17) 0.0607(19) -0.0085(15) -0.0184(15) -0.0166(15) C5B 0.067(2) 0.065(2) 0.068(2) -0.0256(17) -0.0084(17) -0.0138(17) C5C 0.0593(18) 0.0619(19) 0.0541(18) -0.0096(15) -0.0137(15) -0.0127(15) C5D 0.082(3) 0.072(2) 0.074(2) -0.0185(19) -0.0132(19) -0.031(2) C6A 0.0640(19) 0.0567(17) 0.0543(17) -0.0116(14) -0.0155(14) -0.0192(14) C6B 0.0588(17) 0.0581(17) 0.0458(15) -0.0103(13) -0.0094(13) -0.0174(14) C6C 0.0583(18) 0.0616(18) 0.0524(17) -0.0084(14) -0.0121(14) -0.0153(15) C6D 0.070(2) 0.0583(18) 0.0485(16) -0.0030(14) -0.0141(14) -0.0165(15) C7A 0.094(3) 0.062(2) 0.066(2) -0.0193(18) -0.024(2) -0.007(2) C7B 0.074(2) 0.0570(18) 0.0537(18) -0.0028(15) -0.0147(17) -0.0200(16) C7C 0.105(4) 0.088(3) 0.179(6) -0.061(4) -0.061(4) -0.010(3) C7D 0.109(3) 0.092(3) 0.0442(18) -0.0085(18) -0.029(2) -0.019(3) C8A 0.085(3) 0.074(3) 0.075(3) -0.031(2) -0.016(2) -0.006(2) C8B 0.074(2) 0.0555(19) 0.076(2) -0.0063(18) -0.015(2) -0.0197(17) C8C 0.287(12) 0.115(5) 0.413(17) -0.149(8) -0.276(13) 0.070(6) C8D 0.164(6) 0.225(8) 0.047(2) -0.037(3) 0.003(3) -0.112(6) C9A 0.095(3) 0.138(5) 0.093(3) -0.040(3) -0.027(3) -0.030(3) C9B 0.081(3) 0.064(2) 0.078(3) -0.0162(19) -0.023(2) -0.0178(19) C9C 0.118(4) 0.118(4) 0.099(4) -0.045(3) -0.033(3) 0.003(4) C9D 0.181(7) 0.168(7) 0.117(5) -0.084(5) -0.028(5) -0.046(6) C10A 0.130(5) 0.165(6) 0.133(6) -0.020(5) -0.064(4) -0.022(5) C10B 0.084(3) 0.085(3) 0.089(3) -0.022(3) -0.018(3) -0.008(2) C10C 0.126(4) 0.109(4) 0.110(4) -0.040(3) -0.033(3) -0.031(3) C10D 0.208(9) 0.139(6) 0.133(6) -0.048(5) -0.062(6) -0.032(6) C11A 0.0620(19) 0.0536(17) 0.071(2) -0.0198(16) -0.0157(16) -0.0160(15) C11C 0.0564(19) 0.070(2) 0.066(2) -0.0176(17) -0.0088(17) -0.0168(16) C20A 0.0622(19) 0.0581(19) 0.0524(17) -0.0067(15) -0.0094(15) -0.0186(15) C20B 0.0633(19) 0.0611(19) 0.0566(18) -0.0075(15) -0.0171(15) -0.0175(15) C20C 0.070(2) 0.075(2) 0.0444(16) -0.0077(16) -0.0094(15) -0.0212(18) C20D 0.070(2) 0.062(2) 0.0544(18) -0.0084(16) -0.0184(16) -0.0164(17) O1A 0.0601(13) 0.0670(14) 0.0596(13) -0.0155(11) -0.0079(10) -0.0105(11) O1B 0.0680(13) 0.0500(11) 0.0520(12) -0.0094(9) -0.0181(10) -0.0153(10) O1C 0.0659(14) 0.0643(13) 0.0625(13) -0.0159(11) -0.0156(11) -0.0185(11) O1D 0.0805(15) 0.0621(13) 0.0438(11) -0.0110(10) -0.0181(10) -0.0132(11) O2A 0.0805(17) 0.0848(18) 0.0698(16) -0.0220(14) -0.0164(13) -0.0210(14) O2B 0.0679(15) 0.0580(13) 0.0772(16) -0.0138(12) -0.0150(12) -0.0163(11) O2C 0.143(3) 0.087(2) 0.147(3) -0.053(2) -0.074(3) -0.007(2) O2D 0.194(5) 0.183(4) 0.091(3) -0.060(3) -0.010(3) -0.095(4) O3A 0.0724(16) 0.0764(17) 0.0870(19) -0.0254(14) -0.0263(14) -0.0027(13) O3C 0.0644(16) 0.091(2) 0.102(2) -0.0454(17) -0.0163(15) -0.0141(14) O4A 0.0638(16) 0.0846(18) 0.0729(17) -0.0272(14) -0.0071(13) -0.0088(13) _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 C1A O1A 1.372(4) . ? C1A C2A 1.405(4) . ? C1A C6A 1.405(5) . ? C1B O1B 1.396(4) . ? C1B C2B 1.395(5) . ? C1B C6B 1.393(5) . ? C1C O1C 1.373(4) . ? C1C C2C 1.396(5) . ? C1C C6C 1.405(5) . ? C1D O1D 1.388(4) . ? C1D C6D 1.397(5) . ? C1D C2D 1.404(5) . ? C2A C3A 1.388(5) . ? C2A C20A 1.528(5) . ? C2B C3B 1.395(5) . ? C2B C20B 1.527(5) . ? C2C C3C 1.386(5) . ? C2C C20C 1.520(5) . ? C2D C3D 1.388(5) . ? C2D C20D 1.522(5) . ? C3A C4A 1.383(5) . ? C3B C4B 1.379(6) . ? C3C C4C 1.394(5) . ? C3D C4D 1.374(6) . ? C4A C5A 1.405(5) . ? C4A C11A 1.485(5) . ? C4B C5B 1.377(6) . ? C4C C5C 1.397(5) . ? C4C C11C 1.499(5) . ? C4D C5D 1.385(6) . ? C5A C6A 1.384(5) . ? C5B C6B 1.397(5) . ? C5C C6C 1.388(5) . ? C5D C6D 1.395(5) . ? C6A C20D 1.516(5) . ? C6B C20A 1.523(5) . ? C6C C20B 1.525(5) . ? C6D C20C 1.525(5) . ? C7A O1A 1.447(5) . ? C7A C8A 1.502(6) . ? C7B O1B 1.437(4) . ? C7B C8B 1.507(5) . ? C7C C8C 1.286(8) . ? C7C O1C 1.434(5) . ? C7D O1D 1.434(4) . ? C7D C8D 1.484(8) . ? C8A O2A 1.418(5) . ? C8B O2B 1.409(5) . ? C8C O2C 1.415(7) . ? C8D O2D 1.301(7) . ? C9A O2A 1.415(6) . ? C9A C10A 1.488(8) . ? C9B O2B 1.420(5) . ? C9B C10B 1.492(7) . ? C9C O2C 1.379(7) . ? C9C C10C 1.472(7) . ? C9D O2D 1.433(7) . ? C9D C10D 1.488(11) . ? C11A O3A 1.216(4) . ? C11A O4A 1.325(4) . ? C11C O3C 1.425(5) . ? 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 O1A C1A C2A 119.8(3) . . ? O1A C1A C6A 118.3(3) . . ? C2A C1A C6A 121.7(3) . . ? O1B C1B C2B 119.0(3) . . ? O1B C1B C6B 118.9(3) . . ? C2B C1B C6B 122.1(3) . . ? O1C C1C C2C 118.7(3) . . ? O1C C1C C6C 120.0(3) . . ? C2C C1C C6C 121.0(3) . . ? O1D C1D C6D 118.6(3) . . ? O1D C1D C2D 119.2(3) . . ? C6D C1D C2D 122.2(3) . . ? C3A C2A C1A 118.1(3) . . ? C3A C2A C20A 121.7(3) . . ? C1A C2A C20A 120.0(3) . . ? C3B C2B C1B 117.6(3) . . ? C3B C2B C20B 120.0(3) . . ? C1B C2B C20B 122.4(3) . . ? C3C C2C C1C 118.5(3) . . ? C3C C2C C20C 122.0(3) . . ? C1C C2C C20C 119.2(3) . . ? C3D C2D C1D 117.6(3) . . ? C3D C2D C20D 120.7(3) . . ? C1D C2D C20D 121.6(3) . . ? C4A C3A C2A 121.4(3) . . ? C4B C3B C2B 121.2(3) . . ? C2C C3C C4C 122.1(3) . . ? C4D C3D C2D 121.6(4) . . ? C3A C4A C5A 118.9(3) . . ? C3A C4A C11A 122.3(3) . . ? C5A C4A C11A 118.7(3) . . ? C5B C4B C3B 120.3(3) . . ? C3C C4C C5C 117.8(3) . . ? C3C C4C C11C 121.1(3) . . ? C5C C4C C11C 120.9(3) . . ? C3D C4D C5D 119.7(4) . . ? C6A C5A C4A 121.8(3) . . ? C4B C5B C6B 120.5(4) . . ? C4C C5C C6C 122.0(3) . . ? C6D C5D C4D 121.3(4) . . ? C5A C6A C1A 117.3(3) . . ? C5A C6A C20D 122.9(3) . . ? C1A C6A C20D 119.8(3) . . ? C1B C6B C5B 118.3(3) . . ? C1B C6B C20A 122.8(3) . . ? C5B C6B C20A 118.8(3) . . ? C5C C6C C1C 118.2(3) . . ? C5C C6C C20B 121.0(3) . . ? C1C C6C C20B 120.2(3) . . ? C5D C6D C1D 117.4(3) . . ? C5D C6D C20C 119.9(4) . . ? C1D C6D C20C 122.5(3) . . ? O1A C7A C8A 111.6(3) . . ? O1B C7B C8B 108.4(3) . . ? C8C C7C O1C 115.7(5) . . ? O1D C7D C8D 110.3(4) . . ? O2A C8A C7A 108.5(3) . . ? O2B C8B C7B 108.7(3) . . ? C7C C8C O2C 118.9(7) . . ? O2D C8D C7D 116.7(5) . . ? O2A C9A C10A 108.8(5) . . ? O2B C9B C10B 109.0(4) . . ? O2C C9C C10C 110.8(5) . . ? O2D C9D C10D 118.6(6) . . ? O3A C11A O4A 122.6(3) . . ? O3A C11A C4A 123.7(3) . . ? O4A C11A C4A 113.7(3) . . ? O3C C11C C4C 110.2(3) . . ? C6B C20A C2A 110.2(3) . . ? C2B C20B C6C 108.4(3) . . ? C2C C20C C6D 109.9(3) . . ? C6A C20D C2D 110.2(3) . . ? C1A O1A C7A 113.9(3) . . ? C1B O1B C7B 112.6(2) . . ? C1C O1C C7C 114.2(3) . . ? C1D O1D C7D 113.4(3) . . ? C8A O2A C9A 112.1(3) . . ? C8B O2B C9B 112.3(3) . . ? C9C O2C C8C 112.9(6) . . ? C8D O2D C9D 114.9(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 69.89 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.579 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.064