# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Konstantin Udachin' _publ_contact_author_address ; National Research Council Canada Steacie Institute for Molecular Sciences Ottawa CANADA ; _publ_contact_author_email kuku@ned.sims.nrc.ca _publ_section_title ; Supramolecular stabilization of hydroxylamine TEMPOH by complexation with an amphiphilic calixarene ; loop_ _publ_author_name 'Gennady S. Ananchenko' 'Michaela Pojarova' 'Konstantin A. Udachin' 'Donald M. Leek' 'Antony W. Coleman' ; J.A.Ripmeester ; data_gena34 _database_code_depnum_ccdc_archive 'CCDC 279736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63 H91 N O11' _chemical_formula_weight 1038.37 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4572(18) _cell_length_b 22.041(4) _cell_length_c 24.899(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.870(3) _cell_angle_gamma 90.00 _cell_volume 5708.8(17) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 70995 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 29.57 _reflns_number_total 15946 _reflns_number_gt 11373 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0745P)^2^+2.7321P] 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 15946 _refine_ls_number_parameters 729 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.013 _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 O11 O -0.14737(18) 0.74672(8) 0.69210(8) 0.0447(4) Uani 0.72 1 d PD A 11 H11 H -0.129(3) 0.7130(13) 0.7134(12) 0.061(8) Uiso 0.72 1 d P B 11 C62 C -0.2762(3) 0.77410(13) 0.69545(9) 0.0469(6) Uani 0.72 1 d PD A 11 H62A H -0.2660 0.8176 0.7049 0.056 Uiso 0.72 1 calc PR A 11 H62B H -0.3182 0.7539 0.7245 0.056 Uiso 0.72 1 calc PR A 11 C63 C -0.3602(3) 0.76802(11) 0.64295(10) 0.0439(6) Uani 0.72 1 d PD A 11 H63A H -0.3116 0.7802 0.6131 0.053 Uiso 0.72 1 calc PR A 11 H63B H -0.4358 0.7942 0.6436 0.053 Uiso 0.72 1 calc PR A 11 H63C H -0.3878 0.7257 0.6380 0.053 Uiso 0.72 1 calc PR A 11 O11A O -0.2253(9) 0.8215(3) 0.7191(3) 0.0447(4) Uani 0.14 1 d PD C 12 H11A H -0.1591 0.8154 0.7405 0.067 Uiso 0.14 1 calc PR C 12 C62A C -0.2500(13) 0.7697(7) 0.6856(5) 0.0469(6) Uani 0.14 1 d PD C 12 H62C H -0.2518 0.7327 0.7079 0.056 Uiso 0.14 1 calc PR C 12 H62D H -0.1816 0.7651 0.6611 0.056 Uiso 0.14 1 calc PR C 12 C63A C -0.3786(14) 0.7791(7) 0.6532(6) 0.0439(6) Uani 0.14 1 d PD C 12 H63D H -0.4184 0.8163 0.6652 0.053 Uiso 0.14 1 calc PR C 12 H63E H -0.4346 0.7444 0.6585 0.053 Uiso 0.14 1 calc PR C 12 H63F H -0.3663 0.7826 0.6148 0.053 Uiso 0.14 1 calc PR C 12 O11B O -0.0404(8) 0.7424(4) 0.6990(3) 0.0447(4) Uani 0.14 1 d PD D 13 H11B H -0.0232 0.7061 0.6924 0.067 Uiso 0.14 1 calc PR D 13 C62B C -0.1699(11) 0.7526(9) 0.6860(6) 0.0469(6) Uani 0.14 1 d PD D 13 H62E H -0.1978 0.7126 0.6709 0.056 Uiso 0.14 1 calc PR D 13 H62F H -0.1682 0.7790 0.6539 0.056 Uiso 0.14 1 calc PR D 13 C63B C -0.2981(12) 0.7752(6) 0.7088(6) 0.0439(6) Uani 0.14 1 d PD D 13 H63G H -0.3680 0.7467 0.6979 0.053 Uiso 0.14 1 calc PR D 13 H63H H -0.3208 0.8155 0.6942 0.053 Uiso 0.14 1 calc PR D 13 H63I H -0.2847 0.7772 0.7483 0.053 Uiso 0.14 1 calc PR D 13 O1 O 0.32243(9) 0.83774(4) 0.93435(4) 0.0268(2) Uani 1 1 d . . . H4O1 H 0.3314(18) 0.8015(9) 0.9270(8) 0.049(5) Uiso 1 1 d . . . O2 O 0.33648(8) 0.84440(4) 1.05066(4) 0.02316(19) Uani 1 1 d . . . H6O2 H 0.3514(16) 0.8065(8) 1.0490(7) 0.035(4) Uiso 1 1 d . . . O3 O 0.32804(8) 0.72323(4) 1.02746(4) 0.02341(19) Uani 1 1 d . . . H3 H 0.3398(18) 0.7202(8) 0.9926(8) 0.045(5) Uiso 1 1 d . . . O4 O 0.35947(8) 0.72585(4) 0.92505(3) 0.02122(18) Uani 1 1 d . . . O5 O -0.12076(12) 0.92716(5) 0.76318(4) 0.0471(3) Uani 1 1 d . . . O6 O -0.25436(9) 0.91092(4) 1.03011(4) 0.0267(2) Uani 1 1 d . . . O7 O -0.08793(10) 0.52274(4) 1.06373(4) 0.0356(2) Uani 1 1 d . . . O8 O -0.08970(11) 0.63356(5) 0.75325(4) 0.0393(3) Uani 1 1 d . . . O9 O -0.42371(9) 0.71513(5) 0.88483(4) 0.0310(2) Uani 1 1 d . . . H5 H -0.494(2) 0.7171(10) 0.9016(9) 0.068(7) Uiso 1 1 d . . . O10 O 0.56676(9) 0.82549(5) 0.98714(4) 0.0315(2) Uani 1 1 d . . . H101 H 0.489(2) 0.8381(9) 0.9802(8) 0.056(6) Uiso 1 1 d . . . H102 H 0.612(2) 0.8559(10) 1.0013(9) 0.072(7) Uiso 1 1 d . . . N1 N -0.32462(10) 0.74451(5) 0.91843(4) 0.0209(2) Uani 1 1 d . . . H2 H -0.3629(15) 0.7709(7) 0.9403(6) 0.024(4) Uiso 1 1 d . . . C1 C 0.20867(11) 0.72615(5) 0.84564(5) 0.0199(2) Uani 1 1 d . . . C2 C 0.25370(12) 0.78783(5) 0.82799(5) 0.0215(2) Uani 1 1 d . . . H2A H 0.2409 0.7899 0.7881 0.026 Uiso 1 1 calc R . . H2B H 0.3471 0.7914 0.8390 0.026 Uiso 1 1 calc R . . C3 C 0.18594(12) 0.84157(5) 0.85081(5) 0.0198(2) Uani 1 1 d . . . C4 C 0.08781(12) 0.87159(5) 0.82028(5) 0.0208(2) Uani 1 1 d . . . H4 H 0.0590 0.8567 0.7853 0.025 Uiso 1 1 calc R . . C5 C 0.02966(12) 0.92334(5) 0.83954(5) 0.0204(2) Uani 1 1 d . . . C6 C 0.07058(11) 0.94441(5) 0.89143(5) 0.0197(2) Uani 1 1 d . . . H6 H 0.0321 0.9797 0.9047 0.024 Uiso 1 1 calc R . . C7 C 0.16693(11) 0.91448(5) 0.92391(5) 0.0187(2) Uani 1 1 d . . . C8 C 0.21075(12) 0.93480(5) 0.98099(5) 0.0193(2) Uani 1 1 d . . . H8A H 0.1913 0.9785 0.9847 0.023 Uiso 1 1 calc R . . H8B H 0.3050 0.9295 0.9880 0.023 Uiso 1 1 calc R . . C9 C 0.14509(11) 0.89895(5) 1.02251(5) 0.0183(2) Uani 1 1 d . . . C10 C 0.01674(11) 0.90978(5) 1.02829(5) 0.0191(2) Uani 1 1 d . . . H10 H -0.0279 0.9399 1.0064 0.023 Uiso 1 1 calc R . . C11 C -0.04892(12) 0.87786(5) 1.06522(5) 0.0196(2) Uani 1 1 d . . . C12 C 0.01444(12) 0.83105(5) 1.09489(5) 0.0202(2) Uani 1 1 d . . . H12 H -0.0296 0.8089 1.1201 0.024 Uiso 1 1 calc R . . C13 C 0.14111(12) 0.81640(5) 1.08806(5) 0.0189(2) Uani 1 1 d . . . C14 C 0.20226(12) 0.76105(5) 1.11672(5) 0.0206(2) Uani 1 1 d . . . H14A H 0.1730 0.7581 1.1532 0.025 Uiso 1 1 calc R . . H14B H 0.2968 0.7660 1.1210 0.025 Uiso 1 1 calc R . . C15 C 0.16805(12) 0.70263(5) 1.08586(5) 0.0196(2) Uani 1 1 d . . . C16 C 0.07060(12) 0.66534(5) 1.10078(5) 0.0207(2) Uani 1 1 d . . . H16 H 0.0268 0.6761 1.1310 0.025 Uiso 1 1 calc R . . C17 C 0.03571(12) 0.61226(5) 1.07218(5) 0.0203(2) Uani 1 1 d . . . C18 C 0.10066(12) 0.59705(5) 1.02773(5) 0.0204(2) Uani 1 1 d . . . H18 H 0.0773 0.5610 1.0081 0.024 Uiso 1 1 calc R . . C19 C 0.19812(11) 0.63304(5) 1.01145(5) 0.0196(2) Uani 1 1 d . . . C20 C 0.26782(12) 0.61376(5) 0.96339(5) 0.0205(2) Uani 1 1 d . . . H20A H 0.3599 0.6244 0.9708 0.025 Uiso 1 1 calc R . . H20B H 0.2620 0.5691 0.9597 0.025 Uiso 1 1 calc R . . C21 C 0.21571(11) 0.64245(5) 0.91051(5) 0.0197(2) Uani 1 1 d . . . C22 C 0.11833(11) 0.61384(5) 0.87780(5) 0.0205(2) Uani 1 1 d . . . H22 H 0.0867 0.5759 0.8888 0.025 Uiso 1 1 calc R . . C23 C 0.06561(12) 0.63949(6) 0.82914(5) 0.0216(2) Uani 1 1 d . . . C24 C 0.11214(12) 0.69588(5) 0.81405(5) 0.0215(2) Uani 1 1 d . . . H24 H 0.0765 0.7139 0.7812 0.026 Uiso 1 1 calc R . . C25 C 0.22486(11) 0.86357(5) 0.90285(5) 0.0197(2) Uani 1 1 d . . . C26 C 0.20793(11) 0.85245(5) 1.05367(5) 0.0190(2) Uani 1 1 d . . . C27 C 0.23094(11) 0.68625(5) 1.04079(5) 0.0200(2) Uani 1 1 d . . . C28 C 0.26292(11) 0.69856(5) 0.89410(5) 0.0194(2) Uani 1 1 d . . . C29 C -0.07433(13) 0.95303(6) 0.80365(5) 0.0246(3) Uani 1 1 d . . . C30 C -0.12098(13) 1.01568(6) 0.81734(5) 0.0252(3) Uani 1 1 d . . . H30A H -0.0479 1.0444 0.8192 0.030 Uiso 1 1 calc R . . H30B H -0.1533 1.0145 0.8533 0.030 Uiso 1 1 calc R . . C31 C -0.22750(12) 1.03851(6) 0.77585(5) 0.0235(3) Uani 1 1 d . . . H31A H -0.1948 1.0392 0.7399 0.028 Uiso 1 1 calc R . . H31B H -0.3000 1.0095 0.7740 0.028 Uiso 1 1 calc R . . C32 C -0.27739(13) 1.10130(6) 0.78782(5) 0.0248(3) Uani 1 1 d . . . H32A H -0.2057 1.1308 0.7891 0.030 Uiso 1 1 calc R . . H32B H -0.3106 1.1010 0.8237 0.030 Uiso 1 1 calc R . . C33 C -0.38406(13) 1.12130(6) 0.74518(5) 0.0278(3) Uani 1 1 d . . . H33A H -0.3505 1.1213 0.7094 0.033 Uiso 1 1 calc R . . H33B H -0.4553 1.0916 0.7439 0.033 Uiso 1 1 calc R . . C34 C -0.43611(15) 1.18386(7) 0.75593(6) 0.0354(3) Uani 1 1 d . . . H34A H -0.5027 1.1947 0.7269 0.042 Uiso 1 1 calc R . . H34B H -0.3661 1.2136 0.7573 0.042 Uiso 1 1 calc R . . H34C H -0.4731 1.1837 0.7905 0.042 Uiso 1 1 calc R . . C35 C -0.18624(12) 0.89277(5) 1.06988(5) 0.0221(3) Uani 1 1 d . . . C36 C -0.23636(14) 0.88581(7) 1.12395(6) 0.0341(3) Uani 1 1 d . . . H36A H -0.1756 0.9059 1.1515 0.041 Uiso 1 1 calc R . . H36B H -0.2377 0.8421 1.1330 0.041 Uiso 1 1 calc R . . C37 C -0.37058(13) 0.91190(7) 1.12776(6) 0.0334(3) Uani 1 1 d . . . H37A H -0.4024 0.8984 1.1619 0.040 Uiso 1 1 calc R . . H37B H -0.4301 0.8962 1.0975 0.040 Uiso 1 1 calc R . . C38 C -0.36979(14) 0.98143(7) 1.12585(6) 0.0343(3) Uani 1 1 d . . . H38A H -0.3042 0.9963 1.1543 0.041 Uiso 1 1 calc R . . H38B H -0.3427 0.9942 1.0906 0.041 Uiso 1 1 calc R . . C39 C -0.49673(15) 1.01220(7) 1.13334(6) 0.0378(4) Uani 1 1 d . . . H39A H -0.5298 0.9960 1.1663 0.045 Uiso 1 1 calc R . . H39B H -0.4815 1.0562 1.1388 0.045 Uiso 1 1 calc R . . C40 C -0.59746(17) 1.00327(8) 1.08617(7) 0.0458(4) Uani 1 1 d . . . H40A H -0.6741 1.0271 1.0919 0.055 Uiso 1 1 calc R . . H40B H -0.6204 0.9602 1.0831 0.055 Uiso 1 1 calc R . . H40C H -0.5634 1.0167 1.0529 0.055 Uiso 1 1 calc R . . C41 C -0.06837(12) 0.57105(5) 1.08700(5) 0.0235(3) Uani 1 1 d . . . C42 C -0.14794(13) 0.59030(6) 1.13129(5) 0.0256(3) Uani 1 1 d . . . H42A H -0.1854 0.6307 1.1221 0.031 Uiso 1 1 calc R . . H42B H -0.0904 0.5947 1.1652 0.031 Uiso 1 1 calc R . . C43 C -0.25661(13) 0.54690(6) 1.14149(5) 0.0253(3) Uani 1 1 d . . . H43A H -0.2219 0.5051 1.1438 0.030 Uiso 1 1 calc R . . H43B H -0.2863 0.5568 1.1770 0.030 Uiso 1 1 calc R . . C44 C -0.37204(13) 0.54821(6) 1.09895(5) 0.0246(3) Uani 1 1 d . . . H44A H -0.3431 0.5392 1.0632 0.029 Uiso 1 1 calc R . . H44B H -0.4098 0.5894 1.0974 0.029 Uiso 1 1 calc R . . C45 C -0.47470(13) 0.50253(6) 1.11084(6) 0.0280(3) Uani 1 1 d . . . H45A H -0.4978 0.5093 1.1479 0.034 Uiso 1 1 calc R . . H45B H -0.4389 0.4611 1.1093 0.034 Uiso 1 1 calc R . . C46 C -0.59569(15) 0.50696(8) 1.07136(7) 0.0419(4) Uani 1 1 d . . . H46A H -0.6582 0.4766 1.0807 0.050 Uiso 1 1 calc R . . H46B H -0.5737 0.4995 1.0346 0.050 Uiso 1 1 calc R . . H46C H -0.6329 0.5476 1.0734 0.050 Uiso 1 1 calc R . . C47 C -0.03881(13) 0.60916(6) 0.79411(5) 0.0252(3) Uani 1 1 d . . . C48 C -0.08112(13) 0.54667(6) 0.81051(5) 0.0265(3) Uani 1 1 d . . . H48A H -0.1041 0.5489 0.8481 0.032 Uiso 1 1 calc R . . H48B H -0.0070 0.5187 0.8104 0.032 Uiso 1 1 calc R . . C49 C -0.19375(14) 0.51954(6) 0.77539(6) 0.0296(3) Uani 1 1 d . . . H49A H -0.1707 0.5152 0.7380 0.036 Uiso 1 1 calc R . . H49B H -0.2683 0.5473 0.7746 0.036 Uiso 1 1 calc R . . C50 C -0.23115(14) 0.45765(6) 0.79639(6) 0.0298(3) Uani 1 1 d . . . H50A H -0.1569 0.4298 0.7959 0.036 Uiso 1 1 calc R . . H50B H -0.2494 0.4621 0.8344 0.036 Uiso 1 1 calc R . . C51 C -0.34735(15) 0.42886(7) 0.76442(6) 0.0356(3) Uani 1 1 d . . . H51A H -0.4193 0.4583 0.7615 0.043 Uiso 1 1 calc R . . H51B H -0.3259 0.4198 0.7274 0.043 Uiso 1 1 calc R . . C52 C -0.3906(2) 0.37082(8) 0.79002(7) 0.0550(5) Uani 1 1 d . . . H52A H -0.4667 0.3548 0.7684 0.066 Uiso 1 1 calc R . . H52B H -0.4118 0.3794 0.8267 0.066 Uiso 1 1 calc R . . H52C H -0.3212 0.3408 0.7915 0.066 Uiso 1 1 calc R . . C53 C -0.24861(12) 0.78508(6) 0.88270(5) 0.0258(3) Uani 1 1 d . . . C54 C -0.14108(13) 0.81440(6) 0.91985(5) 0.0269(3) Uani 1 1 d . . . H54A H -0.0848 0.8375 0.8976 0.032 Uiso 1 1 calc R . . H54B H -0.1794 0.8436 0.9438 0.032 Uiso 1 1 calc R . . C55 C -0.05930(12) 0.76924(6) 0.95452(5) 0.0262(3) Uani 1 1 d . . . H55A H -0.0160 0.7412 0.9311 0.031 Uiso 1 1 calc R . . H55B H 0.0076 0.7911 0.9780 0.031 Uiso 1 1 calc R . . C56 C -0.14442(12) 0.73343(6) 0.98906(5) 0.0246(3) Uani 1 1 d . . . H56A H -0.1832 0.7618 1.0136 0.030 Uiso 1 1 calc R . . H56B H -0.0903 0.7044 1.0116 0.030 Uiso 1 1 calc R . . C57 C -0.25170(12) 0.69841(6) 0.95647(5) 0.0231(3) Uani 1 1 d . . . C58 C -0.19751(14) 0.74893(8) 0.83743(6) 0.0366(4) Uani 1 1 d . . . H58A H -0.2647 0.7215 0.8214 0.044 Uiso 1 1 calc R . . H58B H -0.1227 0.7251 0.8520 0.044 Uiso 1 1 calc R . . H58C H -0.1722 0.7768 0.8097 0.044 Uiso 1 1 calc R . . C59 C -0.34300(15) 0.83312(8) 0.85856(6) 0.0398(4) Uani 1 1 d . . . H59A H -0.3854 0.8523 0.8875 0.048 Uiso 1 1 calc R . . H59B H -0.4077 0.8139 0.8328 0.048 Uiso 1 1 calc R . . H59C H -0.2963 0.8639 0.8399 0.048 Uiso 1 1 calc R . . C60 C -0.20075(14) 0.64551(6) 0.92546(7) 0.0347(3) Uani 1 1 d . . . H60A H -0.2665 0.6327 0.8969 0.042 Uiso 1 1 calc R . . H60B H -0.1796 0.6116 0.9502 0.042 Uiso 1 1 calc R . . H60C H -0.1234 0.6583 0.9094 0.042 Uiso 1 1 calc R . . C61 C -0.34901(14) 0.67489(7) 0.99293(6) 0.0318(3) Uani 1 1 d . . . H61A H -0.4147 0.6509 0.9715 0.038 Uiso 1 1 calc R . . H61B H -0.3899 0.7093 1.0094 0.038 Uiso 1 1 calc R . . H61C H -0.3051 0.6494 1.0213 0.038 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 O11 0.0527(10) 0.0332(8) 0.0491(9) 0.0074(7) 0.0101(8) 0.0045(7) C62 0.0585(14) 0.0578(13) 0.0298(11) 0.0026(10) 0.0313(9) 0.0050(11) C63 0.0583(14) 0.0319(11) 0.0411(12) 0.0054(9) 0.0033(10) -0.0006(10) O11A 0.0527(10) 0.0332(8) 0.0491(9) 0.0074(7) 0.0101(8) 0.0045(7) C62A 0.0585(14) 0.0578(13) 0.0298(11) 0.0026(10) 0.0313(9) 0.0050(11) C63A 0.0583(14) 0.0319(11) 0.0411(12) 0.0054(9) 0.0033(10) -0.0006(10) O11B 0.0527(10) 0.0332(8) 0.0491(9) 0.0074(7) 0.0101(8) 0.0045(7) C62B 0.0585(14) 0.0578(13) 0.0298(11) 0.0026(10) 0.0313(9) 0.0050(11) C63B 0.0583(14) 0.0319(11) 0.0411(12) 0.0054(9) 0.0033(10) -0.0006(10) O1 0.0247(4) 0.0203(4) 0.0331(5) -0.0059(4) -0.0074(4) 0.0053(4) O2 0.0170(4) 0.0190(4) 0.0327(5) 0.0007(3) -0.0016(3) -0.0001(3) O3 0.0216(4) 0.0199(4) 0.0288(4) -0.0027(3) 0.0027(3) -0.0052(3) O4 0.0150(4) 0.0190(4) 0.0295(4) -0.0028(3) 0.0014(3) -0.0017(3) O5 0.0630(7) 0.0383(6) 0.0347(5) -0.0143(4) -0.0210(5) 0.0230(5) O6 0.0218(4) 0.0298(5) 0.0277(4) -0.0004(4) -0.0018(4) 0.0004(4) O7 0.0424(6) 0.0226(4) 0.0444(5) -0.0084(4) 0.0171(5) -0.0112(4) O8 0.0484(6) 0.0359(5) 0.0305(5) 0.0013(4) -0.0112(5) -0.0104(5) O9 0.0142(4) 0.0517(6) 0.0264(4) -0.0116(4) -0.0007(3) -0.0047(4) O10 0.0181(4) 0.0361(5) 0.0397(5) -0.0123(4) 0.0003(4) 0.0014(4) N1 0.0138(4) 0.0286(5) 0.0200(4) -0.0029(4) -0.0002(4) 0.0002(4) C1 0.0186(5) 0.0169(5) 0.0252(5) -0.0028(4) 0.0072(4) 0.0016(4) C2 0.0222(6) 0.0186(5) 0.0248(5) -0.0010(4) 0.0074(4) 0.0003(4) C3 0.0204(5) 0.0168(5) 0.0229(5) 0.0002(4) 0.0056(4) -0.0017(4) C4 0.0249(6) 0.0185(5) 0.0194(5) -0.0001(4) 0.0044(4) -0.0010(4) C5 0.0229(6) 0.0182(5) 0.0202(5) 0.0014(4) 0.0025(4) 0.0003(4) C6 0.0212(5) 0.0157(5) 0.0223(5) 0.0009(4) 0.0030(4) -0.0005(4) C7 0.0189(5) 0.0157(5) 0.0215(5) -0.0001(4) 0.0022(4) -0.0030(4) C8 0.0204(5) 0.0150(5) 0.0223(5) -0.0010(4) 0.0007(4) -0.0012(4) C9 0.0208(5) 0.0140(5) 0.0197(5) -0.0029(4) -0.0008(4) -0.0019(4) C10 0.0205(5) 0.0165(5) 0.0196(5) -0.0015(4) -0.0016(4) 0.0006(4) C11 0.0197(5) 0.0181(5) 0.0206(5) -0.0039(4) -0.0001(4) -0.0005(4) C12 0.0221(6) 0.0185(5) 0.0197(5) -0.0016(4) 0.0001(4) -0.0022(4) C13 0.0221(5) 0.0153(5) 0.0184(5) -0.0020(4) -0.0031(4) -0.0014(4) C14 0.0236(6) 0.0164(5) 0.0206(5) -0.0005(4) -0.0033(4) 0.0001(4) C15 0.0207(5) 0.0157(5) 0.0211(5) 0.0009(4) -0.0040(4) 0.0013(4) C16 0.0227(6) 0.0187(5) 0.0199(5) 0.0018(4) -0.0015(4) 0.0011(4) C17 0.0207(5) 0.0169(5) 0.0227(5) 0.0022(4) -0.0004(4) -0.0003(4) C18 0.0216(6) 0.0154(5) 0.0233(5) -0.0007(4) -0.0017(4) -0.0001(4) C19 0.0192(5) 0.0162(5) 0.0229(5) -0.0003(4) -0.0008(4) 0.0019(4) C20 0.0187(5) 0.0157(5) 0.0269(6) -0.0018(4) 0.0012(4) 0.0005(4) C21 0.0175(5) 0.0170(5) 0.0249(5) -0.0030(4) 0.0034(4) 0.0011(4) C22 0.0179(5) 0.0180(5) 0.0261(5) -0.0043(4) 0.0047(4) -0.0007(4) C23 0.0189(5) 0.0217(5) 0.0243(5) -0.0053(4) 0.0035(4) -0.0003(4) C24 0.0207(5) 0.0215(5) 0.0225(5) -0.0034(4) 0.0034(4) 0.0025(4) C25 0.0175(5) 0.0181(5) 0.0233(5) 0.0005(4) 0.0010(4) -0.0017(4) C26 0.0179(5) 0.0165(5) 0.0216(5) -0.0038(4) -0.0022(4) -0.0016(4) C27 0.0170(5) 0.0170(5) 0.0251(5) 0.0016(4) -0.0022(4) -0.0001(4) C28 0.0145(5) 0.0183(5) 0.0258(5) -0.0045(4) 0.0039(4) 0.0010(4) C29 0.0289(6) 0.0228(6) 0.0215(5) 0.0002(4) 0.0003(5) 0.0042(5) C30 0.0278(6) 0.0233(6) 0.0235(6) -0.0003(5) -0.0018(5) 0.0057(5) C31 0.0248(6) 0.0224(6) 0.0228(5) 0.0008(4) -0.0001(5) 0.0033(5) C32 0.0266(6) 0.0238(6) 0.0234(6) 0.0005(5) -0.0001(5) 0.0041(5) C33 0.0270(6) 0.0275(6) 0.0282(6) 0.0031(5) -0.0009(5) 0.0042(5) C34 0.0359(8) 0.0324(7) 0.0380(7) 0.0076(6) 0.0042(6) 0.0111(6) C35 0.0212(6) 0.0181(5) 0.0265(6) -0.0005(4) 0.0011(5) -0.0016(4) C36 0.0266(7) 0.0429(8) 0.0337(7) 0.0124(6) 0.0082(5) 0.0071(6) C37 0.0236(6) 0.0419(8) 0.0360(7) 0.0092(6) 0.0097(5) 0.0001(6) C38 0.0288(7) 0.0405(8) 0.0343(7) -0.0006(6) 0.0061(6) -0.0018(6) C39 0.0355(8) 0.0390(8) 0.0389(8) -0.0057(6) 0.0037(6) 0.0003(6) C40 0.0407(9) 0.0422(9) 0.0520(9) -0.0060(7) -0.0079(7) 0.0014(7) C41 0.0252(6) 0.0189(5) 0.0260(6) 0.0015(4) 0.0014(5) -0.0012(5) C42 0.0281(6) 0.0254(6) 0.0235(6) -0.0004(5) 0.0026(5) -0.0039(5) C43 0.0270(6) 0.0266(6) 0.0222(5) 0.0033(5) 0.0023(5) -0.0033(5) C44 0.0265(6) 0.0240(6) 0.0231(5) 0.0020(5) 0.0023(5) -0.0017(5) C45 0.0277(6) 0.0255(6) 0.0310(6) 0.0016(5) 0.0044(5) -0.0025(5) C46 0.0319(8) 0.0534(9) 0.0394(8) -0.0002(7) -0.0005(6) -0.0118(7) C47 0.0256(6) 0.0255(6) 0.0245(6) -0.0060(5) 0.0023(5) -0.0024(5) C48 0.0245(6) 0.0271(6) 0.0273(6) -0.0044(5) -0.0004(5) -0.0048(5) C49 0.0278(7) 0.0285(6) 0.0314(6) -0.0041(5) -0.0019(5) -0.0067(5) C50 0.0319(7) 0.0280(6) 0.0290(6) -0.0022(5) 0.0001(5) -0.0069(5) C51 0.0393(8) 0.0345(7) 0.0329(7) -0.0067(6) 0.0026(6) -0.0126(6) C52 0.0740(12) 0.0456(9) 0.0460(9) -0.0097(7) 0.0100(9) -0.0287(9) C53 0.0194(6) 0.0361(7) 0.0223(5) 0.0042(5) 0.0039(4) 0.0009(5) C54 0.0232(6) 0.0275(6) 0.0303(6) 0.0031(5) 0.0043(5) -0.0027(5) C55 0.0176(6) 0.0287(6) 0.0316(6) -0.0036(5) -0.0011(5) -0.0028(5) C56 0.0202(6) 0.0270(6) 0.0253(6) 0.0017(5) -0.0039(5) -0.0007(5) C57 0.0187(5) 0.0227(6) 0.0275(6) 0.0007(5) 0.0003(5) -0.0001(5) C58 0.0254(7) 0.0599(10) 0.0254(6) -0.0049(6) 0.0072(5) -0.0005(7) C59 0.0334(7) 0.0502(9) 0.0358(7) 0.0182(7) 0.0035(6) 0.0099(7) C60 0.0272(7) 0.0266(7) 0.0505(8) -0.0099(6) 0.0046(6) -0.0002(5) C61 0.0280(7) 0.0335(7) 0.0341(7) 0.0062(6) 0.0048(5) -0.0043(6) _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 O11 C62 1.486(3) . ? C62 C63 1.504(3) . ? O11A C62A 1.422(13) . ? C62A C63A 1.511(15) . ? O11B C62B 1.379(13) . ? C62B C63B 1.588(14) . ? O1 C25 1.3478(14) . ? O2 C26 1.3655(15) . ? O3 C27 1.3690(15) . ? O4 C28 1.3475(14) . ? O5 C29 1.2151(16) . ? O6 C35 1.2263(15) . ? O7 C41 1.2194(16) . ? O8 C47 1.2234(16) . ? O9 N1 1.4199(13) . ? N1 C57 1.5371(16) . ? N1 C53 1.5388(17) . ? C1 C24 1.3856(17) . ? C1 C28 1.4169(17) . ? C1 C2 1.5184(17) . ? C2 C3 1.5200(16) . ? C3 C4 1.3818(17) . ? C3 C25 1.4043(17) . ? C4 C5 1.4002(17) . ? C5 C6 1.3981(16) . ? C5 C29 1.4868(17) . ? C6 C7 1.3920(16) . ? C7 C25 1.4020(16) . ? C7 C8 1.5156(16) . ? C8 C9 1.5198(16) . ? C9 C10 1.3852(17) . ? C9 C26 1.4071(16) . ? C10 C11 1.3931(17) . ? C11 C12 1.3960(16) . ? C11 C35 1.4892(17) . ? C12 C13 1.3905(17) . ? C13 C26 1.4055(17) . ? C13 C14 1.5209(16) . ? C14 C15 1.5232(16) . ? C15 C16 1.3890(17) . ? C15 C27 1.4048(17) . ? C16 C17 1.3987(16) . ? C17 C18 1.3973(17) . ? C17 C41 1.4926(17) . ? C18 C19 1.3845(17) . ? C19 C27 1.4056(16) . ? C19 C20 1.5238(17) . ? C20 C21 1.5113(17) . ? C21 C22 1.3887(16) . ? C21 C28 1.4075(17) . ? C22 C23 1.3980(17) . ? C23 C24 1.4001(17) . ? C23 C47 1.4851(17) . ? C29 C30 1.5150(18) . ? C30 C31 1.5250(17) . ? C31 C32 1.5193(18) . ? C32 C33 1.5245(18) . ? C33 C34 1.516(2) . ? C35 C36 1.5016(19) . ? C36 C37 1.529(2) . ? C37 C38 1.533(2) . ? C38 C39 1.519(2) . ? C39 C40 1.508(2) . ? C41 C42 1.5088(18) . ? C42 C43 1.5264(18) . ? C43 C44 1.5225(18) . ? C44 C45 1.5228(18) . ? C45 C46 1.524(2) . ? C47 C48 1.5154(19) . ? C48 C49 1.5161(18) . ? C49 C50 1.5262(19) . ? C50 C51 1.521(2) . ? C51 C52 1.519(2) . ? C53 C58 1.521(2) . ? C53 C54 1.5248(18) . ? C53 C59 1.528(2) . ? C54 C55 1.5219(19) . ? C55 C56 1.5205(19) . ? C56 C57 1.5254(17) . ? C57 C61 1.5224(19) . ? C57 C60 1.5243(19) . ? 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 O11 C62 C63 111.53(19) . . ? O11A C62A C63A 107.6(11) . . ? O11B C62B C63B 144.2(13) . . ? O9 N1 C57 110.35(9) . . ? O9 N1 C53 108.26(9) . . ? C57 N1 C53 119.17(9) . . ? C24 C1 C28 118.80(11) . . ? C24 C1 C2 119.76(11) . . ? C28 C1 C2 121.44(11) . . ? C1 C2 C3 114.80(10) . . ? C4 C3 C25 118.11(11) . . ? C4 C3 C2 121.06(11) . . ? C25 C3 C2 120.79(11) . . ? C3 C4 C5 121.72(11) . . ? C6 C5 C4 118.98(11) . . ? C6 C5 C29 123.03(11) . . ? C4 C5 C29 117.98(10) . . ? C7 C6 C5 120.95(11) . . ? C6 C7 C25 118.48(10) . . ? C6 C7 C8 122.42(10) . . ? C25 C7 C8 119.10(10) . . ? C7 C8 C9 111.71(9) . . ? C10 C9 C26 118.10(11) . . ? C10 C9 C8 119.41(10) . . ? C26 C9 C8 122.39(11) . . ? C9 C10 C11 121.99(11) . . ? C10 C11 C12 118.89(11) . . ? C10 C11 C35 118.96(10) . . ? C12 C11 C35 122.08(11) . . ? C13 C12 C11 120.89(11) . . ? C12 C13 C26 118.84(11) . . ? C12 C13 C14 119.27(11) . . ? C26 C13 C14 121.87(11) . . ? C13 C14 C15 112.06(9) . . ? C16 C15 C27 118.54(11) . . ? C16 C15 C14 120.41(11) . . ? C27 C15 C14 121.02(11) . . ? C15 C16 C17 121.27(11) . . ? C18 C17 C16 118.78(11) . . ? C18 C17 C41 118.40(11) . . ? C16 C17 C41 122.82(11) . . ? C19 C18 C17 121.76(11) . . ? C18 C19 C27 118.29(11) . . ? C18 C19 C20 119.71(10) . . ? C27 C19 C20 122.00(11) . . ? C21 C20 C19 114.12(10) . . ? C22 C21 C28 119.13(11) . . ? C22 C21 C20 119.89(11) . . ? C28 C21 C20 120.97(10) . . ? C21 C22 C23 121.68(11) . . ? C22 C23 C24 118.32(11) . . ? C22 C23 C47 121.88(11) . . ? C24 C23 C47 119.79(11) . . ? C1 C24 C23 121.87(11) . . ? O1 C25 C7 116.80(10) . . ? O1 C25 C3 121.44(11) . . ? C7 C25 C3 121.73(11) . . ? O2 C26 C13 120.90(10) . . ? O2 C26 C9 118.12(11) . . ? C13 C26 C9 120.96(11) . . ? O3 C27 C15 117.39(10) . . ? O3 C27 C19 121.23(11) . . ? C15 C27 C19 121.35(11) . . ? O4 C28 C21 119.39(10) . . ? O4 C28 C1 120.45(10) . . ? C21 C28 C1 120.16(11) . . ? O5 C29 C5 119.84(12) . . ? O5 C29 C30 120.25(12) . . ? C5 C29 C30 119.90(10) . . ? C29 C30 C31 112.21(10) . . ? C32 C31 C30 114.16(10) . . ? C31 C32 C33 111.61(10) . . ? C34 C33 C32 112.98(11) . . ? O6 C35 C11 119.61(11) . . ? O6 C35 C36 122.02(12) . . ? C11 C35 C36 118.36(11) . . ? C35 C36 C37 115.09(12) . . ? C36 C37 C38 111.48(12) . . ? C39 C38 C37 115.78(13) . . ? C40 C39 C38 113.30(13) . . ? O7 C41 C17 120.33(12) . . ? O7 C41 C42 120.97(12) . . ? C17 C41 C42 118.70(11) . . ? C41 C42 C43 114.90(11) . . ? C44 C43 C42 115.03(10) . . ? C43 C44 C45 112.13(10) . . ? C44 C45 C46 112.81(12) . . ? O8 C47 C23 121.45(12) . . ? O8 C47 C48 120.63(12) . . ? C23 C47 C48 117.92(11) . . ? C47 C48 C49 115.72(11) . . ? C48 C49 C50 111.47(11) . . ? C51 C50 C49 114.36(12) . . ? C52 C51 C50 112.82(13) . . ? C58 C53 C54 112.24(11) . . ? C58 C53 C59 109.47(12) . . ? C54 C53 C59 110.58(12) . . ? C58 C53 N1 111.43(12) . . ? C54 C53 N1 106.74(10) . . ? C59 C53 N1 106.20(11) . . ? C55 C54 C53 113.80(11) . . ? C56 C55 C54 109.44(11) . . ? C55 C56 C57 113.76(11) . . ? C61 C57 C60 109.34(11) . . ? C61 C57 C56 110.80(11) . . ? C60 C57 C56 112.36(11) . . ? C61 C57 N1 105.83(10) . . ? C60 C57 N1 111.76(11) . . ? C56 C57 N1 106.54(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.952 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.055