Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'C. Aakeroy' _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; A pyridyl functionalized cavitand: Starting point for hydrogen-bond driven assembly of heterodimeric capsules ; loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Nate Schultheiss' data_1 _database_code_depnum_ccdc_archive 'CCDC 603465' _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexyl bromo calixarene, acetonitrile ; _chemical_name_common 'hexyl bromo calixarene, acetonitrile' _chemical_melting_point ? _chemical_formula_moiety '(C52 H60 O8 I4) (C2 H3 N)' _chemical_formula_sum 'C54 H63 I4 N O8' _chemical_formula_weight 1361.65 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' I I -0.4742 1.8119 '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 19.045(3) _cell_length_b 16.627(2) _cell_length_c 18.618(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.047(8) _cell_angle_gamma 90.00 _cell_volume 5203.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3398 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 29.55 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2680 _exptl_absorpt_coefficient_mu 2.449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.704 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38563 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 28.38 _reflns_number_total 12203 _reflns_number_gt 7334 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12203 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 N1S N 0.3055(4) 0.4482(4) 0.6216(4) 0.0520(17) Uani 1 1 d . . . C1S C 0.3275(5) 0.3882(5) 0.6486(5) 0.050(2) Uani 1 1 d . . . C2S C 0.3534(6) 0.3079(5) 0.6812(6) 0.069(3) Uani 1 1 d . . . H2A H 0.3993 0.3118 0.7356 0.103 Uiso 1 1 calc R . . H2B H 0.3685 0.2779 0.6453 0.103 Uiso 1 1 calc R . . H2C H 0.3098 0.2799 0.6847 0.103 Uiso 1 1 calc R . . I1 I 0.04677(3) 0.52513(3) 0.10750(2) 0.03167(11) Uani 1 1 d . . . I2 I -0.06735(3) 0.78035(3) 0.31339(3) 0.03449(11) Uani 1 1 d . . . I3 I 0.30839(3) 0.94524(3) 0.48539(3) 0.03854(12) Uani 1 1 d . . . I4 I 0.42213(3) 0.67793(3) 0.27789(3) 0.03685(12) Uani 1 1 d . . . C11 C 0.1030(3) 0.4863(3) 0.2281(3) 0.0209(12) Uani 1 1 d . . . C12 C 0.1814(3) 0.4635(3) 0.2623(3) 0.0197(12) Uani 1 1 d . . . O12 O 0.2180(2) 0.4558(2) 0.2141(2) 0.0248(9) Uani 1 1 d . . . C13 C 0.2228(3) 0.4439(3) 0.3451(3) 0.0185(11) Uani 1 1 d . . . C14 C 0.1819(3) 0.4489(3) 0.3895(3) 0.0182(11) Uani 1 1 d . . . H14A H 0.2098 0.4379 0.4462 0.022 Uiso 1 1 calc R . . C15 C 0.1020(3) 0.4693(3) 0.3553(3) 0.0183(11) Uani 1 1 d . . . C16 C 0.0627(3) 0.4877(3) 0.2734(3) 0.0216(12) Uani 1 1 d . . . O16 O -0.0182(2) 0.5021(2) 0.2338(2) 0.0235(9) Uani 1 1 d . . . C21 C 0.0125(3) 0.6989(3) 0.3981(3) 0.0225(12) Uani 1 1 d . . . C22 C 0.0063(3) 0.6180(3) 0.3776(3) 0.0211(12) Uani 1 1 d . . . O22 O -0.0571(2) 0.5919(2) 0.3059(2) 0.0265(9) Uani 1 1 d . . . C23 C 0.0615(3) 0.5636(3) 0.4304(3) 0.0206(12) Uani 1 1 d . . . C24 C 0.1214(3) 0.5926(3) 0.5039(3) 0.0198(12) Uani 1 1 d . . . H24A H 0.1599 0.5559 0.5404 0.024 Uiso 1 1 calc R . . C25 C 0.1268(3) 0.6729(3) 0.5259(3) 0.0206(12) Uani 1 1 d . . . C26 C 0.0710(3) 0.7254(3) 0.4709(3) 0.0211(12) Uani 1 1 d . . . O26 O 0.0732(2) 0.8057(2) 0.4902(2) 0.0259(9) Uani 1 1 d . . . C31 C 0.3182(3) 0.8311(3) 0.5369(3) 0.0228(12) Uani 1 1 d . . . C32 C 0.2594(4) 0.8065(3) 0.5548(3) 0.0239(13) Uani 1 1 d . . . O32 O 0.2018(2) 0.8609(2) 0.5476(2) 0.0262(9) Uani 1 1 d . . . C33 C 0.2612(3) 0.7303(3) 0.5854(3) 0.0224(12) Uani 1 1 d . . . C34 C 0.3241(3) 0.6795(3) 0.5954(3) 0.0211(12) Uani 1 1 d . . . H34A H 0.3252 0.6262 0.6143 0.025 Uiso 1 1 calc R . . C35 C 0.3838(3) 0.7039(3) 0.5791(3) 0.0217(12) Uani 1 1 d . . . C36 C 0.3802(3) 0.7817(3) 0.5495(3) 0.0223(12) Uani 1 1 d . . . O36 O 0.4415(2) 0.8101(2) 0.5367(2) 0.0271(9) Uani 1 1 d . . . C41 C 0.4073(3) 0.6168(3) 0.3670(3) 0.0241(13) Uani 1 1 d . . . C42 C 0.4346(3) 0.6496(3) 0.4442(3) 0.0207(12) Uani 1 1 d . . . O42 O 0.4777(2) 0.7200(2) 0.4624(2) 0.0240(9) Uani 1 1 d . . . C43 C 0.4227(3) 0.6089(3) 0.5029(3) 0.0187(11) Uani 1 1 d . . . C44 C 0.3833(3) 0.5370(3) 0.4818(3) 0.0207(12) Uani 1 1 d . . . H44A H 0.3741 0.5095 0.5213 0.025 Uiso 1 1 calc R . . C45 C 0.3560(3) 0.5020(3) 0.4057(3) 0.0181(11) Uani 1 1 d . . . C46 C 0.3682(3) 0.5435(4) 0.3479(3) 0.0226(12) Uani 1 1 d . . . O46 O 0.3462(2) 0.5108(2) 0.2726(2) 0.0240(9) Uani 1 1 d . . . C51 C 0.3104(3) 0.4233(3) 0.3826(3) 0.0224(12) Uani 1 1 d . . . H51A H 0.3198 0.3977 0.3393 0.027 Uiso 1 1 calc R . . C52 C 0.3388(4) 0.3639(3) 0.4539(3) 0.0262(13) Uani 1 1 d . . . H52A H 0.3966 0.3552 0.4756 0.031 Uiso 1 1 calc R . . H52B H 0.3307 0.3888 0.4978 0.031 Uiso 1 1 calc R . . C53 C 0.2975(4) 0.2827(4) 0.4334(4) 0.0373(16) Uani 1 1 d . . . H53A H 0.3199 0.2501 0.4838 0.045 Uiso 1 1 calc R . . H53B H 0.2405 0.2915 0.4168 0.045 Uiso 1 1 calc R . . C54 C 0.3028(4) 0.2345(4) 0.3689(4) 0.0393(16) Uani 1 1 d . . . H54A H 0.3593 0.2300 0.3813 0.047 Uiso 1 1 calc R . . H54B H 0.2737 0.2625 0.3160 0.047 Uiso 1 1 calc R . . C55 C 0.2677(5) 0.1494(4) 0.3620(5) 0.053(2) Uani 1 1 d . . . H55A H 0.3015 0.1194 0.4126 0.063 Uiso 1 1 calc R . . H55B H 0.2141 0.1543 0.3576 0.063 Uiso 1 1 calc R . . C56 C 0.2616(5) 0.1024(5) 0.2917(5) 0.064(2) Uani 1 1 d . . . H56A H 0.2395 0.0492 0.2916 0.096 Uiso 1 1 calc R . . H56B H 0.3146 0.0964 0.2959 0.096 Uiso 1 1 calc R . . H56C H 0.2267 0.1306 0.2411 0.096 Uiso 1 1 calc R . . C57 C 0.2654(3) 0.5199(4) 0.2133(3) 0.0245(13) Uani 1 1 d . . . H57A H 0.2446 0.5708 0.2237 0.029 Uiso 1 1 calc R . . H57B H 0.2620 0.5237 0.1587 0.029 Uiso 1 1 calc R . . C61 C 0.0584(3) 0.4763(3) 0.4058(3) 0.0208(12) Uani 1 1 d . . . H61A H 0.0013 0.4632 0.3688 0.025 Uiso 1 1 calc R . . C62 C 0.0875(4) 0.4176(3) 0.4763(4) 0.0268(13) Uani 1 1 d . . . H62A H 0.0587 0.4279 0.5080 0.032 Uiso 1 1 calc R . . H62B H 0.1448 0.4271 0.5127 0.032 Uiso 1 1 calc R . . C63 C 0.0754(4) 0.3301(3) 0.4490(4) 0.0304(14) Uani 1 1 d . . . H63A H 0.0214 0.3131 0.4376 0.037 Uiso 1 1 calc R . . H63B H 0.0788 0.3258 0.3977 0.037 Uiso 1 1 calc R . . C64 C 0.1349(4) 0.2741(4) 0.5104(4) 0.0325(15) Uani 1 1 d . . . H64A H 0.1326 0.2797 0.5622 0.039 Uiso 1 1 calc R . . H64B H 0.1888 0.2903 0.5206 0.039 Uiso 1 1 calc R . . C65 C 0.1219(5) 0.1868(4) 0.4847(5) 0.0465(19) Uani 1 1 d . . . H65A H 0.0717 0.1684 0.4828 0.056 Uiso 1 1 calc R . . H65B H 0.1157 0.1826 0.4290 0.056 Uiso 1 1 calc R . . C66 C 0.1873(6) 0.1320(5) 0.5391(5) 0.064(3) Uani 1 1 d . . . H66A H 0.1747 0.0768 0.5182 0.096 Uiso 1 1 calc R . . H66B H 0.1928 0.1340 0.5941 0.096 Uiso 1 1 calc R . . H66C H 0.2373 0.1489 0.5407 0.096 Uiso 1 1 calc R . . C67 C -0.0424(4) 0.5804(4) 0.2391(4) 0.0271(13) Uani 1 1 d . . . H67A H -0.0914 0.5930 0.1884 0.032 Uiso 1 1 calc R . . H67B H -0.0006 0.6185 0.2436 0.032 Uiso 1 1 calc R . . C71 C 0.1954(3) 0.7042(3) 0.6037(3) 0.0232(12) Uani 1 1 d . . . H71A H 0.1757 0.7541 0.6184 0.028 Uiso 1 1 calc R . . C72 C 0.2228(4) 0.6478(4) 0.6767(3) 0.0265(13) Uani 1 1 d . . . H72A H 0.2355 0.5948 0.6616 0.032 Uiso 1 1 calc R . . H72B H 0.2723 0.6695 0.7218 0.032 Uiso 1 1 calc R . . C73 C 0.1621(4) 0.6361(4) 0.7067(4) 0.0315(14) Uani 1 1 d . . . H73A H 0.1830 0.5955 0.7508 0.038 Uiso 1 1 calc R . . H73B H 0.1130 0.6138 0.6616 0.038 Uiso 1 1 calc R . . C74 C 0.1401(4) 0.7112(4) 0.7385(4) 0.0310(14) Uani 1 1 d . . . H74A H 0.0990 0.6970 0.7547 0.037 Uiso 1 1 calc R . . H74B H 0.1166 0.7512 0.6940 0.037 Uiso 1 1 calc R . . C75 C 0.2107(4) 0.7494(4) 0.8110(4) 0.0325(15) Uani 1 1 d . . . H75A H 0.2370 0.7079 0.8535 0.039 Uiso 1 1 calc R . . H75B H 0.2496 0.7678 0.7934 0.039 Uiso 1 1 calc R . . C76 C 0.1887(5) 0.8197(4) 0.8477(4) 0.0445(18) Uani 1 1 d . . . H76A H 0.2368 0.8412 0.8936 0.067 Uiso 1 1 calc R . . H76B H 0.1514 0.8018 0.8669 0.067 Uiso 1 1 calc R . . H76C H 0.1637 0.8618 0.8065 0.067 Uiso 1 1 calc R . . C77 C 0.1267(4) 0.8539(4) 0.4772(4) 0.0292(14) Uani 1 1 d . . . H77A H 0.1035 0.9082 0.4601 0.035 Uiso 1 1 calc R . . H77B H 0.1343 0.8305 0.4324 0.035 Uiso 1 1 calc R . . C81 C 0.4498(3) 0.6475(3) 0.5859(3) 0.0223(12) Uani 1 1 d . . . H81A H 0.4975 0.6812 0.5978 0.027 Uiso 1 1 calc R . . C82 C 0.4747(3) 0.5854(3) 0.6539(3) 0.0229(12) Uani 1 1 d . . . H82A H 0.4267 0.5590 0.6507 0.027 Uiso 1 1 calc R . . H82B H 0.5078 0.5435 0.6466 0.027 Uiso 1 1 calc R . . C83 C 0.5213(4) 0.6240(4) 0.7368(3) 0.0300(14) Uani 1 1 d . . . H83A H 0.4935 0.6737 0.7387 0.036 Uiso 1 1 calc R . . H83B H 0.5744 0.6398 0.7440 0.036 Uiso 1 1 calc R . . C84 C 0.5322(4) 0.5695(4) 0.8075(4) 0.0368(16) Uani 1 1 d . . . H84A H 0.5525 0.5166 0.8010 0.044 Uiso 1 1 calc R . . H84B H 0.5727 0.5934 0.8591 0.044 Uiso 1 1 calc R . . C85 C 0.4557(4) 0.5570(5) 0.8125(4) 0.0453(18) Uani 1 1 d . . . H85A H 0.4159 0.5316 0.7614 0.054 Uiso 1 1 calc R . . H85B H 0.4347 0.6101 0.8171 0.054 Uiso 1 1 calc R . . C86 C 0.4659(5) 0.5048(5) 0.8840(5) 0.056(2) Uani 1 1 d . . . H86A H 0.4145 0.4989 0.8836 0.084 Uiso 1 1 calc R . . H86B H 0.5041 0.5302 0.9350 0.084 Uiso 1 1 calc R . . H86C H 0.4857 0.4516 0.8793 0.084 Uiso 1 1 calc R . . C87 C 0.4385(4) 0.7915(3) 0.4618(4) 0.0272(13) Uani 1 1 d . . . H87A H 0.3821 0.7871 0.4198 0.033 Uiso 1 1 calc R . . H87B H 0.4626 0.8363 0.4459 0.033 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 N1S 0.055(4) 0.053(4) 0.045(4) 0.002(3) 0.021(3) -0.006(4) C1S 0.050(5) 0.053(5) 0.042(4) 0.000(4) 0.019(4) -0.011(4) C2S 0.064(6) 0.061(6) 0.078(6) 0.015(5) 0.030(5) 0.018(5) I1 0.0287(2) 0.0384(2) 0.02151(19) 0.00346(17) 0.00649(17) -0.00006(19) I2 0.0317(2) 0.0287(2) 0.0356(2) 0.00786(18) 0.00965(19) 0.01095(19) I3 0.0379(3) 0.0215(2) 0.0554(3) 0.00344(19) 0.0212(2) 0.00160(19) I4 0.0442(3) 0.0360(2) 0.0364(2) 0.00447(19) 0.0239(2) -0.0069(2) C11 0.022(3) 0.017(3) 0.015(3) 0.000(2) 0.002(2) -0.001(2) C12 0.021(3) 0.018(3) 0.021(3) 0.000(2) 0.011(2) -0.002(2) O12 0.022(2) 0.030(2) 0.024(2) -0.0065(17) 0.0117(18) -0.0059(18) C13 0.019(3) 0.012(3) 0.027(3) -0.001(2) 0.012(2) -0.002(2) C14 0.016(3) 0.012(3) 0.020(3) 0.000(2) 0.003(2) -0.001(2) C15 0.018(3) 0.010(3) 0.024(3) -0.002(2) 0.008(2) -0.001(2) C16 0.021(3) 0.015(3) 0.025(3) -0.002(2) 0.008(2) -0.003(2) O16 0.015(2) 0.024(2) 0.027(2) -0.0023(17) 0.0067(17) 0.0012(17) C21 0.018(3) 0.019(3) 0.027(3) 0.006(2) 0.009(3) 0.009(2) C22 0.018(3) 0.026(3) 0.021(3) 0.000(2) 0.010(2) 0.003(2) O22 0.017(2) 0.028(2) 0.029(2) -0.0010(18) 0.0064(18) 0.0038(18) C23 0.019(3) 0.018(3) 0.028(3) 0.004(2) 0.014(3) 0.001(2) C24 0.015(3) 0.025(3) 0.019(3) 0.004(2) 0.008(2) 0.006(2) C25 0.018(3) 0.025(3) 0.022(3) 0.003(2) 0.012(2) 0.006(2) C26 0.021(3) 0.022(3) 0.024(3) 0.000(2) 0.013(3) 0.004(2) O26 0.022(2) 0.020(2) 0.034(2) -0.0002(17) 0.0115(19) 0.0060(18) C31 0.023(3) 0.011(3) 0.030(3) 0.001(2) 0.009(3) 0.000(2) C32 0.024(3) 0.021(3) 0.024(3) -0.007(2) 0.010(3) 0.005(3) O32 0.022(2) 0.023(2) 0.032(2) -0.0035(17) 0.0115(19) 0.0037(18) C33 0.022(3) 0.023(3) 0.018(3) -0.005(2) 0.006(2) 0.001(3) C34 0.025(3) 0.019(3) 0.014(3) -0.002(2) 0.005(2) 0.002(2) C35 0.019(3) 0.021(3) 0.020(3) -0.004(2) 0.006(2) 0.004(2) C36 0.018(3) 0.019(3) 0.027(3) -0.003(2) 0.009(3) -0.003(2) O36 0.022(2) 0.023(2) 0.038(2) -0.0026(18) 0.0151(19) -0.0021(18) C41 0.018(3) 0.025(3) 0.032(3) 0.008(2) 0.014(3) 0.006(3) C42 0.012(3) 0.020(3) 0.029(3) 0.001(2) 0.009(2) 0.000(2) O42 0.018(2) 0.021(2) 0.034(2) -0.0013(17) 0.0125(18) -0.0010(17) C43 0.011(3) 0.019(3) 0.022(3) 0.001(2) 0.004(2) 0.001(2) C44 0.014(3) 0.020(3) 0.024(3) 0.003(2) 0.006(2) 0.004(2) C45 0.012(3) 0.019(3) 0.022(3) -0.001(2) 0.007(2) 0.002(2) C46 0.016(3) 0.029(3) 0.020(3) -0.005(2) 0.006(2) -0.004(3) O46 0.022(2) 0.031(2) 0.0220(19) -0.0026(17) 0.0120(18) 0.0002(18) C51 0.024(3) 0.021(3) 0.025(3) -0.001(2) 0.013(3) 0.003(2) C52 0.019(3) 0.024(3) 0.031(3) 0.002(2) 0.008(3) 0.004(3) C53 0.036(4) 0.025(3) 0.049(4) 0.005(3) 0.018(3) 0.002(3) C54 0.048(5) 0.034(4) 0.042(4) 0.005(3) 0.025(4) 0.001(3) C55 0.062(6) 0.036(4) 0.071(5) -0.015(4) 0.040(5) -0.010(4) C56 0.066(6) 0.043(5) 0.084(6) -0.018(4) 0.036(5) -0.004(4) C57 0.025(3) 0.030(3) 0.019(3) -0.001(2) 0.010(3) 0.000(3) C61 0.013(3) 0.026(3) 0.021(3) -0.001(2) 0.006(2) -0.001(2) C62 0.025(3) 0.026(3) 0.031(3) 0.004(3) 0.015(3) 0.002(3) C63 0.031(4) 0.023(3) 0.040(4) 0.011(3) 0.019(3) 0.000(3) C64 0.035(4) 0.024(3) 0.041(4) 0.007(3) 0.021(3) 0.000(3) C65 0.056(5) 0.021(4) 0.060(5) 0.000(3) 0.025(4) 0.000(3) C66 0.097(7) 0.035(4) 0.083(6) 0.025(4) 0.061(6) 0.025(5) C67 0.022(3) 0.025(3) 0.030(3) 0.006(3) 0.009(3) 0.008(3) C71 0.025(3) 0.018(3) 0.028(3) -0.002(2) 0.013(3) 0.003(2) C72 0.034(4) 0.030(3) 0.022(3) 0.002(2) 0.018(3) 0.010(3) C73 0.031(4) 0.036(4) 0.024(3) -0.001(3) 0.010(3) -0.009(3) C74 0.029(4) 0.037(4) 0.031(3) 0.004(3) 0.018(3) 0.002(3) C75 0.029(4) 0.033(4) 0.033(3) 0.002(3) 0.013(3) 0.002(3) C76 0.057(5) 0.033(4) 0.050(4) -0.004(3) 0.031(4) 0.004(4) C77 0.030(4) 0.020(3) 0.036(3) 0.001(3) 0.015(3) 0.009(3) C81 0.019(3) 0.020(3) 0.022(3) -0.003(2) 0.004(2) -0.001(2) C82 0.018(3) 0.021(3) 0.024(3) 0.000(2) 0.006(2) 0.010(2) C83 0.026(3) 0.026(3) 0.025(3) -0.001(3) 0.001(3) 0.007(3) C84 0.041(4) 0.035(4) 0.029(3) -0.003(3) 0.011(3) 0.007(3) C85 0.044(5) 0.054(5) 0.030(4) 0.003(3) 0.011(3) 0.006(4) C86 0.061(6) 0.060(5) 0.052(5) 0.013(4) 0.031(4) 0.012(4) C87 0.026(3) 0.021(3) 0.035(3) 0.002(3) 0.015(3) -0.003(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 N1S C1S 1.107(10) . ? C1S C2S 1.453(12) . ? C2S H2A 0.9800 . ? C2S H2B 0.9800 . ? C2S H2C 0.9800 . ? I1 C11 2.085(5) . ? I2 C21 2.093(5) . ? I3 C31 2.094(5) . ? I4 C41 2.076(5) . ? C11 C12 1.373(8) . ? C11 C16 1.380(8) . ? C12 O12 1.376(6) . ? C12 C13 1.401(7) . ? O12 C57 1.402(7) . ? C13 C14 1.379(7) . ? C13 C51 1.514(8) . ? C14 C15 1.389(7) . ? C14 H14A 0.9500 . ? C15 C16 1.381(7) . ? C15 C61 1.522(7) . ? C16 O16 1.381(7) . ? O16 C67 1.399(7) . ? C21 C26 1.361(8) . ? C21 C22 1.388(8) . ? C22 O22 1.383(7) . ? C22 C23 1.384(8) . ? O22 C67 1.410(7) . ? C23 C24 1.393(8) . ? C23 C61 1.515(8) . ? C24 C25 1.386(8) . ? C24 H24A 0.9500 . ? C25 C26 1.385(8) . ? C25 C71 1.516(8) . ? C26 O26 1.378(7) . ? O26 C77 1.403(7) . ? C31 C36 1.366(8) . ? C31 C32 1.372(8) . ? C32 O32 1.378(7) . ? C32 C33 1.384(8) . ? O32 C77 1.419(7) . ? C33 C34 1.405(8) . ? C33 C71 1.507(8) . ? C34 C35 1.370(8) . ? C34 H34A 0.9500 . ? C35 C36 1.394(8) . ? C35 C81 1.526(8) . ? C36 O36 1.381(7) . ? O36 C87 1.405(7) . ? C41 C46 1.385(8) . ? C41 C42 1.389(8) . ? C42 O42 1.379(7) . ? C42 C43 1.390(7) . ? O42 C87 1.399(7) . ? C43 C44 1.368(8) . ? C43 C81 1.522(7) . ? C44 C45 1.386(7) . ? C44 H44A 0.9500 . ? C45 C46 1.386(7) . ? C45 C51 1.517(8) . ? C46 O46 1.374(6) . ? O46 C57 1.419(7) . ? C51 C52 1.535(8) . ? C51 H51A 1.0000 . ? C52 C53 1.518(9) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.488(9) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.544(9) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.481(10) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C61 C62 1.517(8) . ? C61 H61A 1.0000 . ? C62 C63 1.522(8) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C63 C64 1.496(8) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 C65 1.512(9) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 C66 1.490(10) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? C71 C72 1.527(8) . ? C71 H71A 1.0000 . ? C72 C73 1.515(8) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C73 C74 1.522(9) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 C75 1.526(9) . ? C74 H74A 0.9900 . ? C74 H74B 0.9900 . ? C75 C76 1.510(9) . ? C75 H75A 0.9900 . ? C75 H75B 0.9900 . ? C76 H76A 0.9800 . ? C76 H76B 0.9800 . ? C76 H76C 0.9800 . ? C77 H77A 0.9900 . ? C77 H77B 0.9900 . ? C81 C82 1.526(8) . ? C81 H81A 1.0000 . ? C82 C83 1.515(8) . ? C82 H82A 0.9900 . ? C82 H82B 0.9900 . ? C83 C84 1.530(8) . ? C83 H83A 0.9900 . ? C83 H83B 0.9900 . ? C84 C85 1.519(10) . ? C84 H84A 0.9900 . ? C84 H84B 0.9900 . ? C85 C86 1.522(10) . ? C85 H85A 0.9900 . ? C85 H85B 0.9900 . ? C86 H86A 0.9800 . ? C86 H86B 0.9800 . ? C86 H86C 0.9800 . ? C87 H87A 0.9900 . ? C87 H87B 0.9900 . ? 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 N1S C1S C2S 177.5(10) . . ? C1S C2S H2A 109.5 . . ? C1S C2S H2B 109.5 . . ? H2A C2S H2B 109.5 . . ? C1S C2S H2C 109.5 . . ? H2A C2S H2C 109.5 . . ? H2B C2S H2C 109.5 . . ? C12 C11 C16 121.1(5) . . ? C12 C11 I1 118.7(4) . . ? C16 C11 I1 120.1(4) . . ? C11 C12 O12 119.8(5) . . ? C11 C12 C13 120.1(5) . . ? O12 C12 C13 120.0(5) . . ? C12 O12 C57 117.5(4) . . ? C14 C13 C12 117.5(5) . . ? C14 C13 C51 123.2(5) . . ? C12 C13 C51 119.2(5) . . ? C13 C14 C15 123.1(5) . . ? C13 C14 H14A 118.4 . . ? C15 C14 H14A 118.4 . . ? C16 C15 C14 117.9(5) . . ? C16 C15 C61 119.7(5) . . ? C14 C15 C61 122.3(5) . . ? C11 C16 C15 120.2(5) . . ? C11 C16 O16 118.5(5) . . ? C15 C16 O16 121.1(5) . . ? C16 O16 C67 116.5(4) . . ? C26 C21 C22 120.8(5) . . ? C26 C21 I2 120.3(4) . . ? C22 C21 I2 118.9(4) . . ? O22 C22 C23 120.5(5) . . ? O22 C22 C21 119.4(5) . . ? C23 C22 C21 120.0(5) . . ? C22 O22 C67 116.6(4) . . ? C22 C23 C24 118.0(5) . . ? C22 C23 C61 120.2(5) . . ? C24 C23 C61 121.7(5) . . ? C25 C24 C23 122.4(5) . . ? C25 C24 H24A 118.8 . . ? C23 C24 H24A 118.8 . . ? C26 C25 C24 117.7(5) . . ? C26 C25 C71 120.5(5) . . ? C24 C25 C71 121.6(5) . . ? C21 C26 O26 118.9(5) . . ? C21 C26 C25 121.1(5) . . ? O26 C26 C25 120.0(5) . . ? C26 O26 C77 116.4(4) . . ? C36 C31 C32 121.1(5) . . ? C36 C31 I3 120.5(4) . . ? C32 C31 I3 118.3(4) . . ? C31 C32 O32 118.9(5) . . ? C31 C32 C33 120.6(5) . . ? O32 C32 C33 120.3(5) . . ? C32 O32 C77 116.5(4) . . ? C32 C33 C34 117.3(5) . . ? C32 C33 C71 119.7(5) . . ? C34 C33 C71 123.0(5) . . ? C35 C34 C33 122.6(5) . . ? C35 C34 H34A 118.7 . . ? C33 C34 H34A 118.7 . . ? C34 C35 C36 118.1(5) . . ? C34 C35 C81 122.5(5) . . ? C36 C35 C81 119.3(5) . . ? C31 C36 O36 119.8(5) . . ? C31 C36 C35 120.3(5) . . ? O36 C36 C35 119.8(5) . . ? C36 O36 C87 116.9(4) . . ? C46 C41 C42 120.4(5) . . ? C46 C41 I4 118.9(4) . . ? C42 C41 I4 120.7(4) . . ? O42 C42 C41 118.5(5) . . ? O42 C42 C43 121.2(5) . . ? C41 C42 C43 120.1(5) . . ? C42 O42 C87 117.8(4) . . ? C44 C43 C42 118.0(5) . . ? C44 C43 C81 122.6(5) . . ? C42 C43 C81 119.3(5) . . ? C43 C44 C45 123.4(5) . . ? C43 C44 H44A 118.3 . . ? C45 C44 H44A 118.3 . . ? C44 C45 C46 117.8(5) . . ? C44 C45 C51 122.7(5) . . ? C46 C45 C51 119.4(5) . . ? O46 C46 C41 118.7(5) . . ? O46 C46 C45 120.9(5) . . ? C41 C46 C45 120.3(5) . . ? C46 O46 C57 116.7(4) . . ? C13 C51 C45 107.2(4) . . ? C13 C51 C52 114.0(5) . . ? C45 C51 C52 112.9(5) . . ? C13 C51 H51A 107.5 . . ? C45 C51 H51A 107.5 . . ? C52 C51 H51A 107.5 . . ? C53 C52 C51 115.2(5) . . ? C53 C52 H52A 108.5 . . ? C51 C52 H52A 108.5 . . ? C53 C52 H52B 108.5 . . ? C51 C52 H52B 108.5 . . ? H52A C52 H52B 107.5 . . ? C54 C53 C52 117.4(6) . . ? C54 C53 H53A 108.0 . . ? C52 C53 H53A 108.0 . . ? C54 C53 H53B 108.0 . . ? C52 C53 H53B 108.0 . . ? H53A C53 H53B 107.2 . . ? C53 C54 C55 111.7(6) . . ? C53 C54 H54A 109.3 . . ? C55 C54 H54A 109.3 . . ? C53 C54 H54B 109.3 . . ? C55 C54 H54B 109.3 . . ? H54A C54 H54B 107.9 . . ? C56 C55 C54 114.0(7) . . ? C56 C55 H55A 108.7 . . ? C54 C55 H55A 108.7 . . ? C56 C55 H55B 108.7 . . ? C54 C55 H55B 108.7 . . ? H55A C55 H55B 107.6 . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? O12 C57 O46 112.3(5) . . ? O12 C57 H57A 109.1 . . ? O46 C57 H57A 109.1 . . ? O12 C57 H57B 109.1 . . ? O46 C57 H57B 109.1 . . ? H57A C57 H57B 107.9 . . ? C23 C61 C62 114.1(4) . . ? C23 C61 C15 107.8(4) . . ? C62 C61 C15 113.7(5) . . ? C23 C61 H61A 106.9 . . ? C62 C61 H61A 106.9 . . ? C15 C61 H61A 106.9 . . ? C61 C62 C63 112.9(5) . . ? C61 C62 H62A 109.0 . . ? C63 C62 H62A 109.0 . . ? C61 C62 H62B 109.0 . . ? C63 C62 H62B 109.0 . . ? H62A C62 H62B 107.8 . . ? C64 C63 C62 113.5(5) . . ? C64 C63 H63A 108.9 . . ? C62 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C62 C63 H63B 108.9 . . ? H63A C63 H63B 107.7 . . ? C63 C64 C65 113.8(6) . . ? C63 C64 H64A 108.8 . . ? C65 C64 H64A 108.8 . . ? C63 C64 H64B 108.8 . . ? C65 C64 H64B 108.8 . . ? H64A C64 H64B 107.7 . . ? C66 C65 C64 114.4(7) . . ? C66 C65 H65A 108.7 . . ? C64 C65 H65A 108.7 . . ? C66 C65 H65B 108.7 . . ? C64 C65 H65B 108.7 . . ? H65A C65 H65B 107.6 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? O16 C67 O22 113.4(5) . . ? O16 C67 H67A 108.9 . . ? O22 C67 H67A 108.9 . . ? O16 C67 H67B 108.9 . . ? O22 C67 H67B 108.9 . . ? H67A C67 H67B 107.7 . . ? C33 C71 C25 108.5(4) . . ? C33 C71 C72 113.9(5) . . ? C25 C71 C72 114.8(5) . . ? C33 C71 H71A 106.3 . . ? C25 C71 H71A 106.3 . . ? C72 C71 H71A 106.3 . . ? C73 C72 C71 114.0(5) . . ? C73 C72 H72A 108.7 . . ? C71 C72 H72A 108.7 . . ? C73 C72 H72B 108.7 . . ? C71 C72 H72B 108.7 . . ? H72A C72 H72B 107.6 . . ? C72 C73 C74 115.8(5) . . ? C72 C73 H73A 108.3 . . ? C74 C73 H73A 108.3 . . ? C72 C73 H73B 108.3 . . ? C74 C73 H73B 108.3 . . ? H73A C73 H73B 107.4 . . ? C73 C74 C75 113.3(5) . . ? C73 C74 H74A 108.9 . . ? C75 C74 H74A 108.9 . . ? C73 C74 H74B 108.9 . . ? C75 C74 H74B 108.9 . . ? H74A C74 H74B 107.7 . . ? C76 C75 C74 114.0(6) . . ? C76 C75 H75A 108.8 . . ? C74 C75 H75A 108.8 . . ? C76 C75 H75B 108.8 . . ? C74 C75 H75B 108.8 . . ? H75A C75 H75B 107.7 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? O26 C77 O32 112.8(5) . . ? O26 C77 H77A 109.0 . . ? O32 C77 H77A 109.0 . . ? O26 C77 H77B 109.0 . . ? O32 C77 H77B 109.0 . . ? H77A C77 H77B 107.8 . . ? C43 C81 C35 107.6(4) . . ? C43 C81 C82 112.4(5) . . ? C35 C81 C82 114.1(5) . . ? C43 C81 H81A 107.5 . . ? C35 C81 H81A 107.5 . . ? C82 C81 H81A 107.5 . . ? C83 C82 C81 111.2(5) . . ? C83 C82 H82A 109.4 . . ? C81 C82 H82A 109.4 . . ? C83 C82 H82B 109.4 . . ? C81 C82 H82B 109.4 . . ? H82A C82 H82B 108.0 . . ? C82 C83 C84 113.7(5) . . ? C82 C83 H83A 108.8 . . ? C84 C83 H83A 108.8 . . ? C82 C83 H83B 108.8 . . ? C84 C83 H83B 108.8 . . ? H83A C83 H83B 107.7 . . ? C85 C84 C83 112.9(6) . . ? C85 C84 H84A 109.0 . . ? C83 C84 H84A 109.0 . . ? C85 C84 H84B 109.0 . . ? C83 C84 H84B 109.0 . . ? H84A C84 H84B 107.8 . . ? C84 C85 C86 113.6(6) . . ? C84 C85 H85A 108.8 . . ? C86 C85 H85A 108.8 . . ? C84 C85 H85B 108.8 . . ? C86 C85 H85B 108.8 . . ? H85A C85 H85B 107.7 . . ? C85 C86 H86A 109.5 . . ? C85 C86 H86B 109.5 . . ? H86A C86 H86B 109.5 . . ? C85 C86 H86C 109.5 . . ? H86A C86 H86C 109.5 . . ? H86B C86 H86C 109.5 . . ? O42 C87 O36 114.0(5) . . ? O42 C87 H87A 108.8 . . ? O36 C87 H87A 108.8 . . ? O42 C87 H87B 108.8 . . ? O36 C87 H87B 108.8 . . ? H87A C87 H87B 107.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 O12 174.2(5) . . . . ? I1 C11 C12 O12 -9.1(7) . . . . ? C16 C11 C12 C13 -2.3(8) . . . . ? I1 C11 C12 C13 174.4(4) . . . . ? C11 C12 O12 C57 99.1(6) . . . . ? C13 C12 O12 C57 -84.4(6) . . . . ? C11 C12 C13 C14 -0.3(8) . . . . ? O12 C12 C13 C14 -176.8(5) . . . . ? C11 C12 C13 C51 -176.7(5) . . . . ? O12 C12 C13 C51 6.8(8) . . . . ? C12 C13 C14 C15 2.5(8) . . . . ? C51 C13 C14 C15 178.7(5) . . . . ? C13 C14 C15 C16 -2.1(8) . . . . ? C13 C14 C15 C61 -178.6(5) . . . . ? C12 C11 C16 C15 2.8(8) . . . . ? I1 C11 C16 C15 -173.9(4) . . . . ? C12 C11 C16 O16 -172.7(5) . . . . ? I1 C11 C16 O16 10.7(7) . . . . ? C14 C15 C16 C11 -0.6(8) . . . . ? C61 C15 C16 C11 176.0(5) . . . . ? C14 C15 C16 O16 174.7(5) . . . . ? C61 C15 C16 O16 -8.7(8) . . . . ? C11 C16 O16 C67 -100.4(6) . . . . ? C15 C16 O16 C67 84.2(6) . . . . ? C26 C21 C22 O22 175.2(5) . . . . ? I2 C21 C22 O22 -6.9(7) . . . . ? C26 C21 C22 C23 -1.9(8) . . . . ? I2 C21 C22 C23 175.9(4) . . . . ? C23 C22 O22 C67 -83.4(6) . . . . ? C21 C22 O22 C67 99.5(6) . . . . ? O22 C22 C23 C24 -176.2(5) . . . . ? C21 C22 C23 C24 1.0(8) . . . . ? O22 C22 C23 C61 7.2(8) . . . . ? C21 C22 C23 C61 -175.7(5) . . . . ? C22 C23 C24 C25 0.7(8) . . . . ? C61 C23 C24 C25 177.3(5) . . . . ? C23 C24 C25 C26 -1.3(8) . . . . ? C23 C24 C25 C71 -176.0(5) . . . . ? C22 C21 C26 O26 -177.6(5) . . . . ? I2 C21 C26 O26 4.6(7) . . . . ? C22 C21 C26 C25 1.2(9) . . . . ? I2 C21 C26 C25 -176.6(4) . . . . ? C24 C25 C26 C21 0.4(8) . . . . ? C71 C25 C26 C21 175.1(5) . . . . ? C24 C25 C26 O26 179.2(5) . . . . ? C71 C25 C26 O26 -6.1(8) . . . . ? C21 C26 O26 C77 -98.8(6) . . . . ? C25 C26 O26 C77 82.4(6) . . . . ? C36 C31 C32 O32 174.5(5) . . . . ? I3 C31 C32 O32 -7.9(7) . . . . ? C36 C31 C32 C33 -0.5(9) . . . . ? I3 C31 C32 C33 177.0(4) . . . . ? C31 C32 O32 C77 102.5(6) . . . . ? C33 C32 O32 C77 -82.4(6) . . . . ? C31 C32 C33 C34 -1.5(8) . . . . ? O32 C32 C33 C34 -176.5(5) . . . . ? C31 C32 C33 C71 -179.4(5) . . . . ? O32 C32 C33 C71 5.7(8) . . . . ? C32 C33 C34 C35 2.6(8) . . . . ? C71 C33 C34 C35 -179.6(5) . . . . ? C33 C34 C35 C36 -1.6(8) . . . . ? C33 C34 C35 C81 -176.9(5) . . . . ? C32 C31 C36 O36 -175.2(5) . . . . ? I3 C31 C36 O36 7.3(7) . . . . ? C32 C31 C36 C35 1.6(9) . . . . ? I3 C31 C36 C35 -175.9(4) . . . . ? C34 C35 C36 C31 -0.5(8) . . . . ? C81 C35 C36 C31 175.0(5) . . . . ? C34 C35 C36 O36 176.3(5) . . . . ? C81 C35 C36 O36 -8.2(8) . . . . ? C31 C36 O36 C87 -98.2(6) . . . . ? C35 C36 O36 C87 85.0(6) . . . . ? C46 C41 C42 O42 175.9(5) . . . . ? I4 C41 C42 O42 -5.4(7) . . . . ? C46 C41 C42 C43 -0.1(8) . . . . ? I4 C41 C42 C43 178.6(4) . . . . ? C41 C42 O42 C87 102.1(6) . . . . ? C43 C42 O42 C87 -82.0(6) . . . . ? O42 C42 C43 C44 -176.3(5) . . . . ? C41 C42 C43 C44 -0.5(8) . . . . ? O42 C42 C43 C81 6.9(8) . . . . ? C41 C42 C43 C81 -177.3(5) . . . . ? C42 C43 C44 C45 1.3(8) . . . . ? C81 C43 C44 C45 178.0(5) . . . . ? C43 C44 C45 C46 -1.4(8) . . . . ? C43 C44 C45 C51 -178.3(5) . . . . ? C42 C41 C46 O46 -176.1(5) . . . . ? I4 C41 C46 O46 5.1(7) . . . . ? C42 C41 C46 C45 -0.1(9) . . . . ? I4 C41 C46 C45 -178.8(4) . . . . ? C44 C45 C46 O46 176.8(5) . . . . ? C51 C45 C46 O46 -6.2(8) . . . . ? C44 C45 C46 C41 0.8(8) . . . . ? C51 C45 C46 C41 177.8(5) . . . . ? C41 C46 O46 C57 -100.7(6) . . . . ? C45 C46 O46 C57 83.3(7) . . . . ? C14 C13 C51 C45 -91.8(6) . . . . ? C12 C13 C51 C45 84.4(6) . . . . ? C14 C13 C51 C52 33.8(7) . . . . ? C12 C13 C51 C52 -150.0(5) . . . . ? C44 C45 C51 C13 91.3(6) . . . . ? C46 C45 C51 C13 -85.5(6) . . . . ? C44 C45 C51 C52 -35.0(7) . . . . ? C46 C45 C51 C52 148.2(5) . . . . ? C13 C51 C52 C53 59.8(7) . . . . ? C45 C51 C52 C53 -177.6(5) . . . . ? C51 C52 C53 C54 58.7(8) . . . . ? C52 C53 C54 C55 172.8(6) . . . . ? C53 C54 C55 C56 172.3(7) . . . . ? C12 O12 C57 O46 91.7(6) . . . . ? C46 O46 C57 O12 -90.6(6) . . . . ? C22 C23 C61 C62 -149.0(5) . . . . ? C24 C23 C61 C62 34.5(7) . . . . ? C22 C23 C61 C15 83.7(6) . . . . ? C24 C23 C61 C15 -92.8(6) . . . . ? C16 C15 C61 C23 -82.6(6) . . . . ? C14 C15 C61 C23 93.8(6) . . . . ? C16 C15 C61 C62 149.8(5) . . . . ? C14 C15 C61 C62 -33.8(7) . . . . ? C23 C61 C62 C63 173.8(5) . . . . ? C15 C61 C62 C63 -62.0(6) . . . . ? C61 C62 C63 C64 151.7(5) . . . . ? C62 C63 C64 C65 178.4(6) . . . . ? C63 C64 C65 C66 171.2(6) . . . . ? C16 O16 C67 O22 -90.7(6) . . . . ? C22 O22 C67 O16 91.0(6) . . . . ? C32 C33 C71 C25 84.5(6) . . . . ? C34 C33 C71 C25 -93.3(6) . . . . ? C32 C33 C71 C72 -146.3(5) . . . . ? C34 C33 C71 C72 36.0(7) . . . . ? C26 C25 C71 C33 -84.5(6) . . . . ? C24 C25 C71 C33 90.0(6) . . . . ? C26 C25 C71 C72 146.7(5) . . . . ? C24 C25 C71 C72 -38.7(7) . . . . ? C33 C71 C72 C73 167.2(5) . . . . ? C25 C71 C72 C73 -66.8(6) . . . . ? C71 C72 C73 C74 -62.8(7) . . . . ? C72 C73 C74 C75 -60.5(7) . . . . ? C73 C74 C75 C76 -175.1(5) . . . . ? C26 O26 C77 O32 -92.9(6) . . . . ? C32 O32 C77 O26 93.1(6) . . . . ? C44 C43 C81 C35 -92.2(6) . . . . ? C42 C43 C81 C35 84.4(6) . . . . ? C44 C43 C81 C82 34.2(7) . . . . ? C42 C43 C81 C82 -149.2(5) . . . . ? C34 C35 C81 C43 91.3(6) . . . . ? C36 C35 C81 C43 -84.0(6) . . . . ? C34 C35 C81 C82 -34.1(7) . . . . ? C36 C35 C81 C82 150.6(5) . . . . ? C43 C81 C82 C83 164.9(5) . . . . ? C35 C81 C82 C83 -72.3(6) . . . . ? C81 C82 C83 C84 167.3(5) . . . . ? C82 C83 C84 C85 -71.3(7) . . . . ? C83 C84 C85 C86 -178.3(6) . . . . ? C42 O42 C87 O36 88.8(6) . . . . ? C36 O36 C87 O42 -91.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.860 _refine_diff_density_min -1.547 _refine_diff_density_rms 0.166 #END data_2 _database_code_depnum_ccdc_archive 'CCDC 603466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetra-(3-pyridyl)ethynyl calixarene ; _chemical_name_common 'tetra-(3-pyridyl)ethynyl calixarene' _chemical_melting_point ? _chemical_formula_moiety ; (C80 H76 N4 O8) (C2 H3 N) (H2 O)2 ; _chemical_formula_sum 'C82 H83 N5 O10' _chemical_formula_weight 1298.53 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 Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 25.359(2) _cell_length_b 22.2099(19) _cell_length_c 12.1129(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6822.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8261 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.95 _exptl_crystal_description chip _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2760 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59454 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.29 _reflns_number_total 8904 _reflns_number_gt 7673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+2.5000P] 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 8904 _refine_ls_number_parameters 467 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1401 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _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 O1S O -0.24958(5) 0.2500 -0.2500 0.0264(3) Uani 1 2 d S . . H1 H -0.2284(7) 0.2190(8) -0.2568(15) 0.032 Uiso 1 1 d . . . O2S O -0.2500 0.5000 -0.09137(14) 0.0396(4) Uani 1 2 d S . . H2 H -0.2226(8) 0.5027(10) -0.0377(18) 0.047 Uiso 1 1 d . . . N1S N -0.03285(15) 0.20040(17) -0.7961(4) 0.0647(11) Uani 0.50 1 d P . . C1S C 0.00587(13) 0.22479(15) -0.7712(3) 0.0357(7) Uani 0.50 1 d PD . . C2S C 0.05405(10) 0.2561(6) -0.7423(13) 0.0266(19) Uani 0.50 1 d PD . . H2A H 0.0859(5) 0.2317(9) -0.761(2) 0.040 Uiso 0.50 1 d PD . . H2B H 0.0584(8) 0.2946(8) -0.782(2) 0.040 Uiso 0.50 1 d PD . . H2C H 0.0569(9) 0.2649(13) -0.6626(13) 0.040 Uiso 0.50 1 d PD . . C11 C 0.05956(5) 0.19066(6) -0.06786(10) 0.0189(2) Uani 1 1 d . . . C12 C 0.08274(5) 0.24799(6) -0.06798(10) 0.0189(2) Uani 1 1 d . . . O12 O 0.05743(4) 0.29295(4) -0.12619(8) 0.0214(2) Uani 1 1 d . . . C13 C 0.13034(5) 0.25904(6) -0.01359(10) 0.0177(2) Uani 1 1 d . . . C14 C 0.15426(5) 0.21133(6) 0.04248(10) 0.0177(2) Uani 1 1 d . . . H14A H 0.1863 0.2185 0.0808 0.021 Uiso 1 1 calc R . . C15 C 0.13282(5) 0.15359(6) 0.04426(10) 0.0175(2) Uani 1 1 d . . . C16 C 0.08538(5) 0.14417(6) -0.01141(10) 0.0186(2) Uani 1 1 d . . . O16 O 0.06236(3) 0.08751(4) -0.01392(8) 0.02010(19) Uani 1 1 d . . . C21 C 0.05591(5) 0.41763(6) 0.15588(11) 0.0186(2) Uani 1 1 d . . . C22 C 0.08248(5) 0.42165(6) 0.25711(11) 0.0187(2) Uani 1 1 d . . . O22 O 0.05970(4) 0.45704(4) 0.33862(8) 0.0208(2) Uani 1 1 d . . . C23 C 0.13136(5) 0.39435(5) 0.27371(10) 0.0174(2) Uani 1 1 d . . . C24 C 0.15315(5) 0.36229(6) 0.18592(10) 0.0179(2) Uani 1 1 d . . . H24 H 0.1861 0.3428 0.1965 0.022 Uiso 1 1 calc R . . C25 C 0.12857(5) 0.35769(6) 0.08312(10) 0.0174(2) Uani 1 1 d . . . C26 C 0.07952(5) 0.38551(6) 0.06945(10) 0.0185(2) Uani 1 1 d . . . O26 O 0.05390(4) 0.38571(4) -0.03133(8) 0.02090(19) Uani 1 1 d . . . C31 C 0.15297(5) 0.32263(6) -0.01246(10) 0.0177(2) Uani 1 1 d . . . H31 H 0.1411 0.3427 -0.0821 0.021 Uiso 1 1 calc R . . C32 C 0.21351(5) 0.32495(6) -0.01170(10) 0.0198(2) Uani 1 1 d . . . H32A H 0.2249 0.3672 -0.0019 0.024 Uiso 1 1 calc R . . H32B H 0.2267 0.3016 0.0522 0.024 Uiso 1 1 calc R . . C33 C 0.23839(5) 0.29998(7) -0.11703(11) 0.0243(3) Uani 1 1 d . . . H33A H 0.2215 0.3192 -0.1818 0.029 Uiso 1 1 calc R . . H33B H 0.2315 0.2562 -0.1213 0.029 Uiso 1 1 calc R . . C34 C 0.29796(5) 0.31079(7) -0.12217(12) 0.0282(3) Uani 1 1 d . . . H34A H 0.3103 0.3020 -0.1980 0.034 Uiso 1 1 calc R . . H34B H 0.3049 0.3539 -0.1073 0.034 Uiso 1 1 calc R . . C35 C 0.32990(6) 0.27316(8) -0.04146(13) 0.0321(3) Uani 1 1 d . . . H35A H 0.3265 0.2301 -0.0614 0.038 Uiso 1 1 calc R . . H35B H 0.3153 0.2785 0.0337 0.038 Uiso 1 1 calc R . . C36 C 0.38823(7) 0.29034(11) -0.04093(19) 0.0524(5) Uani 1 1 d . . . H36A H 0.4080 0.2614 0.0040 0.079 Uiso 1 1 calc R . . H36B H 0.3923 0.3308 -0.0098 0.079 Uiso 1 1 calc R . . H36C H 0.4018 0.2898 -0.1167 0.079 Uiso 1 1 calc R . . C37 C 0.02621(5) 0.33319(6) -0.06307(11) 0.0220(3) Uani 1 1 d . . . H37A H -0.0051 0.3450 -0.1069 0.026 Uiso 1 1 calc R . . H37B H 0.0136 0.3122 0.0040 0.026 Uiso 1 1 calc R . . C41 C 0.15649(5) 0.39758(6) 0.38771(10) 0.0179(2) Uani 1 1 d . . . H41 H 0.1448 0.4362 0.4223 0.021 Uiso 1 1 calc R . . C42 C 0.21685(5) 0.39827(6) 0.38542(11) 0.0197(2) Uani 1 1 d . . . H42A H 0.2296 0.3595 0.3551 0.024 Uiso 1 1 calc R . . H42B H 0.2288 0.4308 0.3354 0.024 Uiso 1 1 calc R . . C43 C 0.24129(5) 0.40797(6) 0.49916(11) 0.0218(3) Uani 1 1 d . . . H43A H 0.2281 0.4463 0.5304 0.026 Uiso 1 1 calc R . . H43B H 0.2302 0.3750 0.5489 0.026 Uiso 1 1 calc R . . C44 C 0.30124(5) 0.40985(7) 0.49388(12) 0.0252(3) Uani 1 1 d . . . H44A H 0.3138 0.3733 0.4553 0.030 Uiso 1 1 calc R . . H44B H 0.3120 0.4451 0.4492 0.030 Uiso 1 1 calc R . . C45 C 0.32837(6) 0.41356(8) 0.60548(13) 0.0325(3) Uani 1 1 d . . . H45A H 0.3167 0.3794 0.6521 0.039 Uiso 1 1 calc R . . H45B H 0.3179 0.4514 0.6428 0.039 Uiso 1 1 calc R . . C46 C 0.38840(6) 0.41183(10) 0.59343(17) 0.0498(5) Uani 1 1 d . . . H46A H 0.3987 0.3755 0.5529 0.075 Uiso 1 1 calc R . . H46B H 0.4047 0.4114 0.6668 0.075 Uiso 1 1 calc R . . H46C H 0.4003 0.4475 0.5528 0.075 Uiso 1 1 calc R . . C47 C 0.03051(5) 0.42691(6) 0.42147(11) 0.0209(3) Uani 1 1 d . . . H47A H 0.0154 0.3894 0.3904 0.025 Uiso 1 1 calc R . . H47B H 0.0009 0.4529 0.4456 0.025 Uiso 1 1 calc R . . N51 N -0.16922(4) 0.15950(6) -0.25919(10) 0.0252(2) Uani 1 1 d . . . C52 C -0.12396(5) 0.17636(6) -0.21223(11) 0.0228(3) Uani 1 1 d . . . H52 H -0.1225 0.2150 -0.1786 0.027 Uiso 1 1 calc R . . C53 C -0.07872(5) 0.14073(6) -0.20951(10) 0.0196(2) Uani 1 1 d . . . C54 C -0.08205(5) 0.08332(6) -0.25574(12) 0.0241(3) Uani 1 1 d . . . H54 H -0.0523 0.0573 -0.2559 0.029 Uiso 1 1 calc R . . C55 C -0.12949(5) 0.06473(6) -0.30154(12) 0.0256(3) Uani 1 1 d . . . H55 H -0.1330 0.0254 -0.3315 0.031 Uiso 1 1 calc R . . C56 C -0.17163(5) 0.10439(7) -0.30291(11) 0.0248(3) Uani 1 1 d . . . H56 H -0.2037 0.0918 -0.3364 0.030 Uiso 1 1 calc R . . C57 C -0.03091(5) 0.16202(6) -0.15992(11) 0.0210(3) Uani 1 1 d . . . C58 C 0.01015(5) 0.17803(6) -0.12066(10) 0.0201(2) Uani 1 1 d . . . N61 N -0.17606(5) 0.50563(7) 0.09226(14) 0.0406(3) Uani 1 1 d . . . C62 C -0.12748(6) 0.48255(7) 0.08707(14) 0.0328(3) Uani 1 1 d . . . H62 H -0.1202 0.4537 0.0313 0.039 Uiso 1 1 calc R . . C63 C -0.08706(5) 0.49837(6) 0.15852(11) 0.0216(3) Uani 1 1 d . . . C64 C -0.09791(6) 0.54096(7) 0.23981(12) 0.0263(3) Uani 1 1 d . . . H64 H -0.0712 0.5537 0.2896 0.032 Uiso 1 1 calc R . . C65 C -0.14846(6) 0.56440(7) 0.24657(13) 0.0305(3) Uani 1 1 d . . . H65 H -0.1571 0.5931 0.3017 0.037 Uiso 1 1 calc R . . C66 C -0.18592(6) 0.54535(7) 0.17201(14) 0.0336(3) Uani 1 1 d . . . H66 H -0.2205 0.5614 0.1778 0.040 Uiso 1 1 calc R . . C67 C -0.03641(5) 0.47049(6) 0.14917(11) 0.0217(3) Uani 1 1 d . . . C68 C 0.00547(5) 0.44602(6) 0.14524(11) 0.0205(3) 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 O1S 0.0147(6) 0.0266(7) 0.0378(8) -0.0012(6) 0.000 0.000 O2S 0.0291(8) 0.0557(11) 0.0339(8) 0.000 0.000 0.0106(7) N1S 0.0458(19) 0.053(2) 0.096(3) -0.034(2) -0.0003(19) -0.0106(16) C1S 0.0358(16) 0.0313(15) 0.0401(17) -0.0052(13) 0.0010(13) 0.0021(13) C2S 0.0213(9) 0.022(5) 0.037(4) 0.004(3) -0.002(2) -0.0032(17) C11 0.0146(5) 0.0240(6) 0.0182(6) -0.0031(5) -0.0007(4) 0.0001(5) C12 0.0163(5) 0.0220(6) 0.0185(6) -0.0002(5) -0.0007(4) 0.0011(5) O12 0.0212(4) 0.0223(5) 0.0208(4) 0.0005(4) -0.0043(3) 0.0026(4) C13 0.0147(5) 0.0203(6) 0.0179(5) -0.0017(4) 0.0017(4) -0.0001(4) C14 0.0125(5) 0.0222(6) 0.0183(5) -0.0020(5) 0.0009(4) 0.0005(4) C15 0.0140(5) 0.0200(6) 0.0185(5) -0.0019(4) 0.0012(4) 0.0018(4) C16 0.0159(5) 0.0202(6) 0.0198(6) -0.0035(5) 0.0015(4) -0.0011(4) O16 0.0191(4) 0.0195(4) 0.0217(4) -0.0038(3) -0.0004(3) -0.0028(3) C21 0.0146(5) 0.0169(5) 0.0244(6) 0.0025(5) 0.0000(4) 0.0004(4) C22 0.0164(5) 0.0160(5) 0.0238(6) -0.0007(5) 0.0014(5) 0.0000(4) O22 0.0206(4) 0.0179(4) 0.0240(5) -0.0019(4) 0.0018(3) 0.0024(3) C23 0.0141(5) 0.0163(5) 0.0218(6) 0.0011(4) -0.0007(4) -0.0024(4) C24 0.0129(5) 0.0176(5) 0.0232(6) 0.0012(5) 0.0004(4) -0.0011(4) C25 0.0143(5) 0.0166(5) 0.0213(6) 0.0010(4) 0.0019(4) -0.0016(4) C26 0.0161(5) 0.0176(6) 0.0218(6) 0.0026(5) -0.0011(4) -0.0014(4) O26 0.0202(4) 0.0210(4) 0.0215(4) 0.0022(3) -0.0035(3) 0.0015(3) C31 0.0153(5) 0.0193(6) 0.0186(5) 0.0007(5) 0.0004(4) 0.0000(4) C32 0.0154(5) 0.0223(6) 0.0218(6) 0.0000(5) 0.0016(4) -0.0012(5) C33 0.0196(6) 0.0286(7) 0.0247(6) -0.0007(5) 0.0034(5) 0.0006(5) C34 0.0207(6) 0.0322(7) 0.0319(7) 0.0032(6) 0.0084(5) 0.0020(5) C35 0.0230(7) 0.0375(8) 0.0357(8) 0.0052(7) 0.0057(6) 0.0039(6) C36 0.0212(8) 0.0717(14) 0.0645(12) 0.0196(11) 0.0051(8) 0.0043(8) C37 0.0162(6) 0.0245(6) 0.0254(6) -0.0001(5) -0.0041(5) 0.0018(5) C41 0.0138(5) 0.0187(6) 0.0212(6) -0.0022(5) -0.0008(4) -0.0012(4) C42 0.0140(5) 0.0219(6) 0.0233(6) -0.0013(5) -0.0003(4) -0.0031(5) C43 0.0162(6) 0.0257(6) 0.0235(6) -0.0034(5) -0.0011(5) -0.0027(5) C44 0.0165(6) 0.0323(7) 0.0269(7) -0.0056(6) -0.0027(5) -0.0014(5) C45 0.0242(7) 0.0417(9) 0.0316(7) -0.0130(6) -0.0083(6) 0.0029(6) C46 0.0244(8) 0.0737(13) 0.0511(11) -0.0305(10) -0.0154(7) 0.0099(8) C47 0.0159(6) 0.0224(6) 0.0244(6) -0.0028(5) 0.0010(5) 0.0024(5) N51 0.0195(5) 0.0286(6) 0.0276(6) -0.0011(5) -0.0036(4) 0.0033(5) C52 0.0223(6) 0.0225(6) 0.0236(6) -0.0011(5) -0.0021(5) 0.0011(5) C53 0.0164(6) 0.0236(6) 0.0188(6) 0.0023(5) -0.0016(4) -0.0021(5) C54 0.0204(6) 0.0225(6) 0.0293(7) 0.0011(5) -0.0040(5) 0.0025(5) C55 0.0250(7) 0.0218(6) 0.0301(7) -0.0019(5) -0.0047(5) -0.0012(5) C56 0.0191(6) 0.0301(7) 0.0252(6) 0.0000(5) -0.0047(5) -0.0029(5) C57 0.0191(6) 0.0234(6) 0.0206(6) 0.0016(5) -0.0005(5) 0.0001(5) C58 0.0184(6) 0.0229(6) 0.0192(6) -0.0004(5) -0.0003(5) 0.0008(5) N61 0.0251(6) 0.0423(8) 0.0544(9) -0.0023(7) -0.0132(6) 0.0076(6) C62 0.0265(7) 0.0331(8) 0.0389(8) -0.0074(6) -0.0087(6) 0.0080(6) C63 0.0183(6) 0.0211(6) 0.0254(6) 0.0042(5) 0.0003(5) 0.0027(5) C64 0.0239(6) 0.0283(7) 0.0265(7) 0.0000(5) 0.0004(5) 0.0022(5) C65 0.0304(7) 0.0286(7) 0.0326(7) 0.0021(6) 0.0088(6) 0.0080(6) C66 0.0211(7) 0.0318(8) 0.0479(9) 0.0092(7) 0.0035(6) 0.0090(6) C67 0.0203(6) 0.0217(6) 0.0232(6) 0.0006(5) -0.0012(5) 0.0008(5) C68 0.0200(6) 0.0193(6) 0.0223(6) 0.0001(5) -0.0007(5) 0.0003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1S H1 0.876(18) 4_554 ? O1S H1 0.876(18) . ? O2S H2 0.95(2) 2_465 ? O2S H2 0.95(2) . ? N1S C1S 1.161(5) . ? C1S C2S 1.449(8) . ? C2S H2A 0.999(9) . ? C2S H2B 0.989(9) . ? C2S H2C 0.987(9) . ? C11 C16 1.4009(18) . ? C11 C12 1.4024(18) . ? C11 C58 1.4344(17) . ? C12 O12 1.3806(15) . ? C12 C13 1.3970(17) . ? O12 C37 1.4179(16) . ? C13 C14 1.3969(17) . ? C13 C31 1.5247(17) . ? C14 C15 1.3931(17) . ? C14 H14A 0.9500 . ? C15 C16 1.3949(17) . ? C15 C41 1.5268(17) 4 ? C16 O16 1.3877(15) . ? O16 C47 1.4174(16) 4 ? C21 C26 1.4012(18) . ? C21 C22 1.4019(18) . ? C21 C68 1.4319(17) . ? C22 O22 1.3878(15) . ? C22 C23 1.3944(17) . ? O22 C47 1.4151(16) . ? C23 C24 1.3940(17) . ? C23 C41 1.5226(17) . ? C24 C25 1.3964(17) . ? C24 H24 0.9500 . ? C25 C26 1.3986(17) . ? C25 C31 1.5263(17) . ? C26 O26 1.3829(15) . ? O26 C37 1.4147(16) . ? C31 C32 1.5359(17) . ? C31 H31 1.0000 . ? C32 C33 1.5276(18) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.5308(19) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.520(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.527(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C41 C15 1.5267(17) 4 ? C41 C42 1.5309(16) . ? C41 H41 1.0000 . ? C42 C43 1.5259(18) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.5222(17) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.5191(19) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.530(2) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 O16 1.4173(16) 4 ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? N51 C52 1.3345(17) . ? N51 C56 1.3350(19) . ? C52 C53 1.3941(18) . ? C52 H52 0.9500 . ? C53 C54 1.3951(19) . ? C53 C57 1.4334(18) . ? C54 C55 1.3877(19) . ? C54 H54 0.9500 . ? C55 C56 1.385(2) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C57 C58 1.1986(19) . ? N61 C66 1.332(2) . ? N61 C62 1.336(2) . ? C62 C63 1.3867(19) . ? C62 H62 0.9500 . ? C63 C64 1.393(2) . ? C63 C67 1.4305(18) . ? C64 C65 1.386(2) . ? C64 H64 0.9500 . ? C65 C66 1.377(2) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C67 C68 1.1940(18) . ? 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 H1 O1S H1 104(2) 4_554 . ? H2 O2S H2 94(2) 2_465 . ? N1S C1S C2S 178.7(8) . . ? C1S C2S H2A 111.4(13) . . ? C1S C2S H2B 113.0(12) . . ? H2A C2S H2B 105.4(14) . . ? C1S C2S H2C 113.2(12) . . ? H2A C2S H2C 105.8(14) . . ? H2B C2S H2C 107.6(15) . . ? C16 C11 C12 118.27(11) . . ? C16 C11 C58 118.81(12) . . ? C12 C11 C58 122.90(12) . . ? O12 C12 C13 121.03(11) . . ? O12 C12 C11 117.54(11) . . ? C13 C12 C11 121.41(12) . . ? C12 O12 C37 116.11(10) . . ? C14 C13 C12 118.11(12) . . ? C14 C13 C31 122.33(11) . . ? C12 C13 C31 119.49(11) . . ? C15 C14 C13 122.44(11) . . ? C15 C14 H14A 118.8 . . ? C13 C14 H14A 118.8 . . ? C14 C15 C16 117.84(11) . . ? C14 C15 C41 122.70(11) . 4 ? C16 C15 C41 119.23(11) . 4 ? O16 C16 C15 120.62(11) . . ? O16 C16 C11 117.46(11) . . ? C15 C16 C11 121.92(12) . . ? C16 O16 C47 115.30(10) . 4 ? C26 C21 C22 118.72(11) . . ? C26 C21 C68 122.59(12) . . ? C22 C21 C68 118.68(11) . . ? O22 C22 C23 120.90(11) . . ? O22 C22 C21 117.28(11) . . ? C23 C22 C21 121.71(11) . . ? C22 O22 C47 117.03(10) . . ? C24 C23 C22 117.68(11) . . ? C24 C23 C41 123.36(11) . . ? C22 C23 C41 118.84(11) . . ? C23 C24 C25 122.72(11) . . ? C23 C24 H24 118.6 . . ? C25 C24 H24 118.6 . . ? C24 C25 C26 118.05(11) . . ? C24 C25 C31 122.19(11) . . ? C26 C25 C31 119.75(11) . . ? O26 C26 C25 121.58(11) . . ? O26 C26 C21 117.20(11) . . ? C25 C26 C21 121.10(11) . . ? C26 O26 C37 118.06(10) . . ? C13 C31 C25 109.07(10) . . ? C13 C31 C32 114.03(10) . . ? C25 C31 C32 112.56(10) . . ? C13 C31 H31 106.9 . . ? C25 C31 H31 106.9 . . ? C32 C31 H31 106.9 . . ? C33 C32 C31 113.31(11) . . ? C33 C32 H32A 108.9 . . ? C31 C32 H32A 108.9 . . ? C33 C32 H32B 108.9 . . ? C31 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C32 C33 C34 112.62(12) . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33B 109.1 . . ? C34 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? C35 C34 C33 114.42(12) . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 112.42(14) . . ? C34 C35 H35A 109.1 . . ? C36 C35 H35A 109.1 . . ? C34 C35 H35B 109.1 . . ? C36 C35 H35B 109.1 . . ? H35A C35 H35B 107.9 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O26 C37 O12 112.90(10) . . ? O26 C37 H37A 109.0 . . ? O12 C37 H37A 109.0 . . ? O26 C37 H37B 109.0 . . ? O12 C37 H37B 109.0 . . ? H37A C37 H37B 107.8 . . ? C23 C41 C15 106.85(10) . 4 ? C23 C41 C42 113.74(10) . . ? C15 C41 C42 114.22(10) 4 . ? C23 C41 H41 107.2 . . ? C15 C41 H41 107.2 4 . ? C42 C41 H41 107.2 . . ? C43 C42 C41 113.02(10) . . ? C43 C42 H42A 109.0 . . ? C41 C42 H42A 109.0 . . ? C43 C42 H42B 109.0 . . ? C41 C42 H42B 109.0 . . ? H42A C42 H42B 107.8 . . ? C44 C43 C42 111.81(11) . . ? C44 C43 H43A 109.3 . . ? C42 C43 H43A 109.3 . . ? C44 C43 H43B 109.3 . . ? C42 C43 H43B 109.3 . . ? H43A C43 H43B 107.9 . . ? C45 C44 C43 114.61(12) . . ? C45 C44 H44A 108.6 . . ? C43 C44 H44A 108.6 . . ? C45 C44 H44B 108.6 . . ? C43 C44 H44B 108.6 . . ? H44A C44 H44B 107.6 . . ? C44 C45 C46 111.37(13) . . ? C44 C45 H45A 109.4 . . ? C46 C45 H45A 109.4 . . ? C44 C45 H45B 109.4 . . ? C46 C45 H45B 109.4 . . ? H45A C45 H45B 108.0 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O22 C47 O16 111.66(10) . 4 ? O22 C47 H47A 109.3 . . ? O16 C47 H47A 109.3 4 . ? O22 C47 H47B 109.3 . . ? O16 C47 H47B 109.3 4 . ? H47A C47 H47B 108.0 . . ? C52 N51 C56 117.75(12) . . ? N51 C52 C53 123.96(13) . . ? N51 C52 H52 118.0 . . ? C53 C52 H52 118.0 . . ? C52 C53 C54 117.36(12) . . ? C52 C53 C57 121.24(12) . . ? C54 C53 C57 121.40(12) . . ? C55 C54 C53 119.00(12) . . ? C55 C54 H54 120.5 . . ? C53 C54 H54 120.5 . . ? C56 C55 C54 118.98(13) . . ? C56 C55 H55 120.5 . . ? C54 C55 H55 120.5 . . ? N51 C56 C55 122.89(12) . . ? N51 C56 H56 118.6 . . ? C55 C56 H56 118.6 . . ? C58 C57 C53 177.35(15) . . ? C57 C58 C11 173.56(14) . . ? C66 N61 C62 117.48(14) . . ? N61 C62 C63 123.71(14) . . ? N61 C62 H62 118.1 . . ? C63 C62 H62 118.1 . . ? C62 C63 C64 117.86(13) . . ? C62 C63 C67 120.30(13) . . ? C64 C63 C67 121.82(12) . . ? C65 C64 C63 118.66(14) . . ? C65 C64 H64 120.7 . . ? C63 C64 H64 120.7 . . ? C66 C65 C64 118.92(14) . . ? C66 C65 H65 120.5 . . ? C64 C65 H65 120.5 . . ? N61 C66 C65 123.34(14) . . ? N61 C66 H66 118.3 . . ? C65 C66 H66 118.3 . . ? C68 C67 C63 177.36(15) . . ? C67 C68 C21 172.51(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 O12 178.49(11) . . . . ? C58 C11 C12 O12 -3.01(18) . . . . ? C16 C11 C12 C13 0.03(18) . . . . ? C58 C11 C12 C13 178.53(12) . . . . ? C13 C12 O12 C37 -81.83(14) . . . . ? C11 C12 O12 C37 99.70(13) . . . . ? O12 C12 C13 C14 -179.09(11) . . . . ? C11 C12 C13 C14 -0.69(18) . . . . ? O12 C12 C13 C31 3.84(18) . . . . ? C11 C12 C13 C31 -177.75(11) . . . . ? C12 C13 C14 C15 1.08(18) . . . . ? C31 C13 C14 C15 178.06(11) . . . . ? C13 C14 C15 C16 -0.78(18) . . . . ? C13 C14 C15 C41 -175.32(11) . . . 4 ? C14 C15 C16 O16 179.17(11) . . . . ? C41 C15 C16 O16 -6.09(17) 4 . . . ? C14 C15 C16 C11 0.07(18) . . . . ? C41 C15 C16 C11 174.81(11) 4 . . . ? C12 C11 C16 O16 -178.84(11) . . . . ? C58 C11 C16 O16 2.60(17) . . . . ? C12 C11 C16 C15 0.29(19) . . . . ? C58 C11 C16 C15 -178.28(11) . . . . ? C15 C16 O16 C47 84.52(14) . . . 4 ? C11 C16 O16 C47 -96.35(13) . . . 4 ? C26 C21 C22 O22 175.88(11) . . . . ? C68 C21 C22 O22 -4.71(17) . . . . ? C26 C21 C22 C23 -0.34(18) . . . . ? C68 C21 C22 C23 179.07(12) . . . . ? C23 C22 O22 C47 -84.27(14) . . . . ? C21 C22 O22 C47 99.48(13) . . . . ? O22 C22 C23 C24 -176.44(11) . . . . ? C21 C22 C23 C24 -0.35(18) . . . . ? O22 C22 C23 C41 7.35(17) . . . . ? C21 C22 C23 C41 -176.57(11) . . . . ? C22 C23 C24 C25 1.26(18) . . . . ? C41 C23 C24 C25 177.29(11) . . . . ? C23 C24 C25 C26 -1.42(18) . . . . ? C23 C24 C25 C31 179.76(11) . . . . ? C24 C25 C26 O26 176.58(11) . . . . ? C31 C25 C26 O26 -4.57(18) . . . . ? C24 C25 C26 C21 0.67(18) . . . . ? C31 C25 C26 C21 179.52(11) . . . . ? C22 C21 C26 O26 -175.91(11) . . . . ? C68 C21 C26 O26 4.70(18) . . . . ? C22 C21 C26 C25 0.17(18) . . . . ? C68 C21 C26 C25 -179.21(12) . . . . ? C25 C26 O26 C37 79.50(15) . . . . ? C21 C26 O26 C37 -104.43(13) . . . . ? C14 C13 C31 C25 -91.40(13) . . . . ? C12 C13 C31 C25 85.54(14) . . . . ? C14 C13 C31 C32 35.38(16) . . . . ? C12 C13 C31 C32 -147.69(11) . . . . ? C24 C25 C31 C13 95.01(13) . . . . ? C26 C25 C31 C13 -83.79(14) . . . . ? C24 C25 C31 C32 -32.60(16) . . . . ? C26 C25 C31 C32 148.60(11) . . . . ? C13 C31 C32 C33 65.38(14) . . . . ? C25 C31 C32 C33 -169.68(11) . . . . ? C31 C32 C33 C34 171.78(11) . . . . ? C32 C33 C34 C35 70.79(17) . . . . ? C33 C34 C35 C36 -173.83(15) . . . . ? C26 O26 C37 O12 -92.01(13) . . . . ? C12 O12 C37 O26 93.85(13) . . . . ? C24 C23 C41 C15 -92.01(13) . . . 4 ? C22 C23 C41 C15 83.98(13) . . . 4 ? C24 C23 C41 C42 34.98(17) . . . . ? C22 C23 C41 C42 -149.04(11) . . . . ? C23 C41 C42 C43 174.12(11) . . . . ? C15 C41 C42 C43 -62.85(14) 4 . . . ? C41 C42 C43 C44 -178.72(11) . . . . ? C42 C43 C44 C45 -174.59(12) . . . . ? C43 C44 C45 C46 176.92(15) . . . . ? C22 O22 C47 O16 92.03(12) . . . 4 ? C56 N51 C52 C53 2.3(2) . . . . ? N51 C52 C53 C54 -2.2(2) . . . . ? N51 C52 C53 C57 178.54(13) . . . . ? C52 C53 C54 C55 0.0(2) . . . . ? C57 C53 C54 C55 179.26(13) . . . . ? C53 C54 C55 C56 1.9(2) . . . . ? C52 N51 C56 C55 -0.1(2) . . . . ? C54 C55 C56 N51 -1.9(2) . . . . ? C66 N61 C62 C63 -1.1(3) . . . . ? N61 C62 C63 C64 -0.3(2) . . . . ? N61 C62 C63 C67 178.50(15) . . . . ? C62 C63 C64 C65 1.2(2) . . . . ? C67 C63 C64 C65 -177.57(13) . . . . ? C63 C64 C65 C66 -0.8(2) . . . . ? C62 N61 C66 C65 1.5(3) . . . . ? C64 C65 C66 N61 -0.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1S H1 N51 0.876(18) 2.000(19) 2.8644(15) 168.4(17) . O2S H2 N61 0.95(2) 1.97(2) 2.912(2) 169.7(18) . _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 29.29 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.519 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.065 #END