# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jerry L. Atwood' _publ_contact_author_address ; 125, Chemistry University of Missouri-Columbia 601 South College Avenue Columbia MO 65211 USA ; _publ_contact_author_email AtwoodJ@missouri.edu _publ_contact_author_phone 1(573)8828374 _publ_contact_author_fax 1(573)8848374 loop_ _publ_author_name _publ_author_address G.W.V.Cave ; School of Biomedical & Natural Sciences Nottingham Trent University Clifton Lane Nottingham NG11 8NS UK ; M.C.Ferrarelli ; 125, Chemistry University of Missouri-Columbia 601 South College Avenue Columbia MO 65211 USA ; J.L.Atwood ; 125, Chemistry University of Missouri-Columbia 601 South College Avenue Columbia MO 65211 USA ; _publ_section_title ; Nano-dimensions for the pyrogallol[4]arene cavity ; data_nano-cups _database_code_depnum_ccdc_archive 'CCDC 249861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,8,14,20-tetrapropyl-4,5,6,10,11,12,16,17,18,22,23,24 -dodecahydroxycalix(4)arene bis(4-(pyridin-4-yl)pyridine) propanone clathrate ; _chemical_name_common ; 2,8,14,20-tetrapropyl-4,5,6,10,11,12,16,17,18,22,23,24 - dodecahydroxycalix(4)arene bis(4-(pyridin-4-yl)pyridine) propanone clathrate ; _chemical_melting_point ? _chemical_formula_moiety ; (C40H48O12) (N2C10H8)2 OC3H6 ; _chemical_formula_sum 'C63 H70 N4 O13' _chemical_formula_weight 1091.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/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 21.480(8) _cell_length_b 15.086(6) _cell_length_c 18.231(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.750(6) _cell_angle_gamma 90.00 _cell_volume 5560(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prisum _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 61206 _diffrn_reflns_av_R_equivalents 0.1979 _diffrn_reflns_av_sigmaI/netI 0.1861 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 27.19 _reflns_number_total 12344 _reflns_number_gt 4831 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'enCIFer (CCDC, 2003)' _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. After anisotropic refinement of all non-hydrogen atoms, aromatic and methylene hydrogen atoms were placed by modeling the moieties as rigid groups with idealized geometry, maximizing the sum of the electron density at the calculated hydrogen positions. All hydroxyl hydrogen atoms were located in order that a detailed understanding of the hydrogen bonding interactions can be understood. ; _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^)+(0.1191P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 12344 _refine_ls_number_parameters 812 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2362 _refine_ls_R_factor_gt 0.0875 _refine_ls_wR_factor_ref 0.2581 _refine_ls_wR_factor_gt 0.1937 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.467 _refine_ls_shift/su_mean 0.011 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.19608(16) 0.5253(2) 0.27214(19) 0.0454(9) Uani 1 1 d . . . N1 N 0.5745(2) 0.3049(3) 0.5596(2) 0.0482(11) Uani 1 1 d . . . C1 C 0.2919(2) 0.3716(3) 0.1992(2) 0.0314(11) Uani 1 1 d . . . H1 H 0.2852 0.3343 0.1553 0.038 Uiso 1 1 calc R . . O2 O 0.31511(18) 0.5259(2) 0.39206(19) 0.0499(10) Uani 1 1 d . . . N2 N 0.6980(2) 0.3744(3) 0.9680(2) 0.0443(10) Uani 1 1 d . . . C2 C 0.2394(2) 0.4218(3) 0.2024(2) 0.0304(11) Uani 1 1 d . . . H2 H -0.021(3) 0.417(4) 0.227(3) 0.081(19) Uiso 1 1 d . . . O3 O 0.41829(15) 0.4341(2) 0.38547(17) 0.0450(9) Uani 1 1 d . . . N3 N 0.0802(2) 0.7855(3) 0.6979(2) 0.0452(10) Uani 1 1 d . . . C3 C 0.2488(2) 0.4741(3) 0.2686(3) 0.0346(11) Uani 1 1 d . . . H3 H 0.110(3) 0.498(3) 0.229(3) 0.072(18) Uiso 1 1 d . . . O4 O 0.49854(15) 0.2925(2) 0.40816(19) 0.0387(8) Uani 1 1 d . . . N4 N 0.1888(2) 0.6069(4) 0.4019(3) 0.0639(14) Uani 1 1 d . . . C4 C 0.3084(2) 0.4749(3) 0.3270(2) 0.0359(11) Uani 1 1 d . . . H4 H -0.020(2) 0.194(3) 0.229(3) 0.028(16) Uiso 1 1 d . . . H6 H 0.277(6) -0.088(8) 0.445(7) 0.095(17) Uiso 1 1 d . . . O5 O 0.50240(15) 0.1426(2) 0.49217(17) 0.0416(9) Uani 1 1 d . . . C5 C 0.3610(2) 0.4257(3) 0.3223(2) 0.0335(11) Uani 1 1 d . . . H5 H 0.451(2) 0.367(4) 0.399(3) 0.077(17) Uiso 1 1 d . . . O6 O 0.42324(17) 0.0015(2) 0.43004(17) 0.0385(8) Uani 1 1 d . . . C6 C 0.3549(2) 0.3720(3) 0.2569(2) 0.0301(11) Uani 1 1 d . . . O7 O 0.29839(16) -0.0721(2) 0.39041(19) 0.0417(9) Uani 1 1 d . . . C7 C 0.4114(2) 0.3166(3) 0.2526(2) 0.0342(11) Uani 1 1 d . . . H7 H 0.4528 0.3506 0.2793 0.041 Uiso 1 1 calc R . . O8 O 0.17219(18) -0.0643(2) 0.39522(18) 0.0480(9) Uani 1 1 d . . . C8 C 0.4100(2) 0.2982(3) 0.1686(2) 0.0416(12) Uani 1 1 d . . . H8A H 0.4499 0.2636 0.1712 0.050 Uiso 1 1 calc R . . H8B H 0.3709 0.2612 0.1418 0.050 Uiso 1 1 calc R . . O9 O 0.07502(16) 0.0202(2) 0.28511(19) 0.0409(9) Uani 1 1 d . . . C9 C 0.4076(3) 0.3822(4) 0.1192(3) 0.0715(18) Uani 1 1 d . . . H9A H 0.4067 0.3635 0.0668 0.086 Uiso 1 1 calc R . . H9B H 0.3656 0.4137 0.1126 0.086 Uiso 1 1 calc R . . O10 O 0.00547(19) 0.1720(2) 0.2193(2) 0.0424(10) Uani 1 1 d . . . C10 C 0.4609(3) 0.4430(4) 0.1500(4) 0.092(2) Uani 1 1 d . . . H10A H 0.4583 0.4693 0.1981 0.138 Uiso 1 1 calc R . . H10B H 0.4578 0.4900 0.1118 0.138 Uiso 1 1 calc R . . H10C H 0.5030 0.4117 0.1613 0.138 Uiso 1 1 calc R . . H10 H 0.052(2) 0.064(3) 0.259(3) 0.054(17) Uiso 1 1 d . . . O11 O -0.01515(16) 0.3509(2) 0.22944(18) 0.0442(9) Uani 1 1 d . . . C11 C 0.3747(2) 0.1588(3) 0.2669(2) 0.0315(11) Uani 1 1 d . . . H11 H 0.3443 0.1645 0.2154 0.038 Uiso 1 1 calc R . . O12 O 0.06677(16) 0.4715(2) 0.19932(18) 0.0402(8) Uani 1 1 d . . . C12 C 0.4155(2) 0.2301(3) 0.2987(2) 0.0300(11) Uani 1 1 d . . . H12 H 0.133(3) -0.037(5) 0.390(4) 0.13(3) Uiso 1 1 d . . . C13 C 0.4582(2) 0.2228(3) 0.3749(2) 0.0307(11) Uani 1 1 d . . . H13 H 0.355(2) 0.510(3) 0.425(3) 0.058(17) Uiso 1 1 d . . . C14 C 0.4591(2) 0.1447(3) 0.4164(2) 0.0316(11) Uani 1 1 d . . . H14 H 0.387(3) -0.025(3) 0.416(3) 0.059(18) Uiso 1 1 d . . . C15 C 0.4182(2) 0.0749(3) 0.3834(2) 0.0300(10) Uani 1 1 d . . . H15 H 0.514(3) 0.085(4) 0.500(3) 0.10(2) Uiso 1 1 d . . . C16 C 0.3756(2) 0.0796(3) 0.3057(2) 0.0281(10) Uani 1 1 d . . . H16 H 0.527(3) 0.277(4) 0.459(4) 0.11(2) Uiso 1 1 d . . . C17 C 0.3337(2) 0.0007(3) 0.2654(2) 0.0305(11) Uani 1 1 d . . . H17 H 0.3545 -0.0530 0.2959 0.037 Uiso 1 1 calc R . . C18 C 0.3343(2) -0.0136(3) 0.1822(2) 0.0405(12) Uani 1 1 d . . . H18A H 0.3067 -0.0660 0.1599 0.049 Uiso 1 1 calc R . . H18B H 0.3132 0.0384 0.1503 0.049 Uiso 1 1 calc R . . H18 H 0.208(3) 0.557(4) 0.318(4) 0.09(2) Uiso 1 1 d . . . C19 C 0.4007(3) -0.0269(4) 0.1746(3) 0.0629(16) Uani 1 1 d . . . H19A H 0.4195 -0.0834 0.2001 0.076 Uiso 1 1 calc R . . H19B H 0.4304 0.0215 0.2025 0.076 Uiso 1 1 calc R . . C20 C 0.3994(3) -0.0288(5) 0.0909(3) 0.092(2) Uani 1 1 d . . . H20A H 0.3719 -0.0784 0.0634 0.138 Uiso 1 1 calc R . . H20B H 0.4445 -0.0364 0.0902 0.138 Uiso 1 1 calc R . . H20C H 0.3811 0.0270 0.0651 0.138 Uiso 1 1 calc R . . C21 C 0.2136(2) 0.0503(3) 0.2123(2) 0.0303(11) Uani 1 1 d . . . H21 H 0.2237 0.0776 0.1707 0.036 Uiso 1 1 calc R . . C22 C 0.2641(2) 0.0066(3) 0.2686(2) 0.0277(10) Uani 1 1 d . . . C23 C 0.2491(2) -0.0297(3) 0.3318(2) 0.0331(11) Uani 1 1 d . . . C24 C 0.1858(2) -0.0243(3) 0.3336(2) 0.0327(11) Uani 1 1 d . . . C25 C 0.1367(2) 0.0194(3) 0.2763(2) 0.0306(11) Uani 1 1 d . . . C26 C 0.1492(2) 0.0569(3) 0.2125(2) 0.0280(10) Uani 1 1 d . . . C27 C 0.0942(2) 0.1036(3) 0.1485(2) 0.0311(11) Uani 1 1 d . . . H27 H 0.0518 0.0767 0.1491 0.037 Uiso 1 1 calc R . . C28 C 0.0979(2) 0.0847(3) 0.0669(2) 0.0376(12) Uani 1 1 d . . . H28A H 0.1381 0.1131 0.0628 0.045 Uiso 1 1 calc R . . H28B H 0.1021 0.0200 0.0609 0.045 Uiso 1 1 calc R . . C29 C 0.0389(2) 0.1176(3) 0.0019(2) 0.0496(14) Uani 1 1 d . . . H29A H 0.0361 0.1828 0.0060 0.060 Uiso 1 1 calc R . . H29B H -0.0016 0.0918 0.0074 0.060 Uiso 1 1 calc R . . C30 C 0.0417(3) 0.0942(4) -0.0776(3) 0.0759(19) Uani 1 1 d . . . H30A H 0.0788 0.1254 -0.0859 0.114 Uiso 1 1 calc R . . H30B H 0.0003 0.1119 -0.1179 0.114 Uiso 1 1 calc R . . H30C H 0.0479 0.0301 -0.0806 0.114 Uiso 1 1 calc R . . C31 C 0.1303(2) 0.2636(3) 0.1474(2) 0.0310(11) Uani 1 1 d . . . H31 H 0.1630 0.2429 0.1272 0.037 Uiso 1 1 calc R . . C32 C 0.0901(2) 0.2015(3) 0.1648(2) 0.0291(10) Uani 1 1 d . . . C33 C 0.0431(2) 0.2329(3) 0.1962(2) 0.0321(11) Uani 1 1 d . . . C34 C 0.0351(2) 0.3234(3) 0.2039(2) 0.0327(11) Uani 1 1 d . . . C35 C 0.0772(2) 0.3830(3) 0.1865(2) 0.0307(11) Uani 1 1 d . . . C36 C 0.1258(2) 0.3536(3) 0.1574(2) 0.0280(10) Uani 1 1 d . . . C37 C 0.1723(2) 0.4189(3) 0.1376(2) 0.0297(10) Uani 1 1 d . . . H37 H 0.1522 0.4792 0.1349 0.036 Uiso 1 1 calc R . . C38 C 0.1769(2) 0.3994(3) 0.0567(2) 0.0379(12) Uani 1 1 d . . . H38A H 0.2077 0.4425 0.0464 0.045 Uiso 1 1 calc R . . H38B H 0.1960 0.3395 0.0576 0.045 Uiso 1 1 calc R . . C39 C 0.1116(2) 0.4037(3) -0.0095(3) 0.0497(14) Uani 1 1 d . . . H39A H 0.1195 0.3933 -0.0592 0.060 Uiso 1 1 calc R . . H39B H 0.0826 0.3555 -0.0029 0.060 Uiso 1 1 calc R . . C40 C 0.0766(3) 0.4901(5) -0.0143(3) 0.087(2) Uani 1 1 d . . . H40A H 0.0551 0.4918 0.0253 0.130 Uiso 1 1 calc R . . H40B H 0.0432 0.4966 -0.0661 0.130 Uiso 1 1 calc R . . H40C H 0.1086 0.5387 -0.0051 0.130 Uiso 1 1 calc R . . C41 C 0.6330(3) 0.2728(4) 0.6020(3) 0.0587(15) Uani 1 1 d . . . H41 H 0.6575 0.2412 0.5759 0.070 Uiso 1 1 calc R . . C42 C 0.6607(3) 0.2826(3) 0.6826(3) 0.0588(15) Uani 1 1 d . . . H42 H 0.7031 0.2587 0.7101 0.071 Uiso 1 1 calc R . . C43 C 0.6255(2) 0.3275(3) 0.7216(3) 0.0412(12) Uani 1 1 d . . . C44 C 0.5651(2) 0.3613(4) 0.6771(3) 0.0520(14) Uani 1 1 d . . . H44 H 0.5395 0.3936 0.7015 0.062 Uiso 1 1 calc R . . C45 C 0.5411(3) 0.3488(4) 0.5975(3) 0.0519(14) Uani 1 1 d . . . H45 H 0.4990 0.3725 0.5685 0.062 Uiso 1 1 calc R . . C46 C 0.7379(2) 0.3751(3) 0.9253(3) 0.0468(13) Uani 1 1 d . . . H46 H 0.7835 0.3871 0.9513 0.056 Uiso 1 1 calc R . . C47 C 0.7175(2) 0.3596(3) 0.8463(3) 0.0430(12) Uani 1 1 d . . . H47 H 0.7482 0.3616 0.8192 0.052 Uiso 1 1 calc R . . C48 C 0.6515(2) 0.3411(3) 0.8070(3) 0.0429(12) Uani 1 1 d . . . C49 C 0.6100(3) 0.3385(4) 0.8512(3) 0.0610(17) Uani 1 1 d . . . H49 H 0.5644 0.3250 0.8274 0.073 Uiso 1 1 calc R . . C50 C 0.6359(3) 0.3558(4) 0.9299(3) 0.0605(16) Uani 1 1 d . . . H50 H 0.6065 0.3540 0.9587 0.073 Uiso 1 1 calc R . . C51 C 0.1240(3) 0.7200(4) 0.7115(3) 0.0527(14) Uani 1 1 d . . . H51 H 0.1389 0.6951 0.7624 0.063 Uiso 1 1 calc R . . C52 C 0.1494(2) 0.6856(3) 0.6579(3) 0.0464(13) Uani 1 1 d . . . H52 H 0.1815 0.6396 0.6721 0.056 Uiso 1 1 calc R . . C53 C 0.1272(2) 0.7194(3) 0.5820(3) 0.0388(12) Uani 1 1 d . A . C54 C 0.0816(2) 0.7885(3) 0.5670(3) 0.0437(13) Uani 1 1 d . . . H54 H 0.0650 0.8145 0.5166 0.052 Uiso 1 1 calc R . . C55 C 0.0610(2) 0.8189(3) 0.6267(3) 0.0495(14) Uani 1 1 d . . . H55 H 0.0309 0.8672 0.6158 0.059 Uiso 1 1 calc R . . C56 C 0.1499(2) 0.6820(3) 0.5188(3) 0.0413(12) Uani 1 1 d . . . C61 C 0.1949(5) 0.2247(9) -0.1241(7) 0.222(7) Uani 1 1 d . . . H61A H 0.1792 0.1653 -0.1431 0.334 Uiso 1 1 calc R . . H61B H 0.2064 0.2570 -0.1644 0.334 Uiso 1 1 calc R . . H61C H 0.1599 0.2567 -0.1118 0.334 Uiso 1 1 calc R . . C62 C 0.2527(4) 0.2176(6) -0.0546(5) 0.097(2) Uani 1 1 d . . . C63 C 0.3121(5) 0.2433(9) -0.0610(7) 0.223(7) Uani 1 1 d . . . H63A H 0.3273 0.2978 -0.0311 0.335 Uiso 1 1 calc R . . H63B H 0.3063 0.2540 -0.1159 0.335 Uiso 1 1 calc R . . H63C H 0.3449 0.1963 -0.0405 0.335 Uiso 1 1 calc R . . O64 O 0.2511(3) 0.1895(5) 0.0076(4) 0.151(2) Uani 1 1 d . . . C57A C 0.1375(7) 0.7222(9) 0.4517(7) 0.056(4) Uani 0.50 1 d P A 1 H57A H 0.1160 0.7782 0.4425 0.067 Uiso 0.50 1 calc PR A 1 C58A C 0.1560(10) 0.6819(12) 0.3953(10) 0.071(6) Uani 0.50 1 d P A 1 H58A H 0.1440 0.7110 0.3463 0.085 Uiso 0.50 1 calc PR A 1 C59A C 0.1983(6) 0.5629(8) 0.4722(6) 0.053(3) Uani 0.50 1 d P A 1 H59A H 0.2166 0.5049 0.4791 0.064 Uiso 0.50 1 calc PR A 1 C60A C 0.1820(5) 0.6009(7) 0.5315(6) 0.042(3) Uani 0.50 1 d P A 1 H60A H 0.1925 0.5720 0.5805 0.050 Uiso 0.50 1 calc PR A 1 C57B C 0.1097(6) 0.6718(11) 0.4399(7) 0.061(4) Uani 0.50 1 d P A 2 H57B H 0.0653 0.6925 0.4230 0.073 Uiso 0.50 1 calc PR A 2 C58B C 0.1342(8) 0.6321(12) 0.3869(10) 0.064(5) Uani 0.50 1 d P A 2 H58B H 0.1050 0.6248 0.3349 0.077 Uiso 0.50 1 calc PR A 2 C59B C 0.2371(7) 0.6256(12) 0.4750(8) 0.099(6) Uani 0.50 1 d P A 2 H59B H 0.2824 0.6128 0.4843 0.119 Uiso 0.50 1 calc PR A 2 C60B C 0.2176(7) 0.6621(10) 0.5317(7) 0.084(4) Uani 0.50 1 d P A 2 H60B H 0.2498 0.6747 0.5810 0.100 Uiso 0.50 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.051(2) 0.046(2) 0.0349(19) -0.0119(17) 0.0081(17) 0.0058(17) N1 0.064(3) 0.045(3) 0.028(2) -0.003(2) 0.006(2) -0.010(2) C1 0.042(3) 0.031(3) 0.019(2) 0.0042(19) 0.008(2) -0.004(2) O2 0.055(2) 0.055(2) 0.0313(19) -0.0141(17) 0.0040(18) 0.0080(19) N2 0.046(3) 0.061(3) 0.025(2) -0.0022(19) 0.011(2) -0.005(2) C2 0.042(3) 0.025(2) 0.023(2) 0.0045(19) 0.010(2) -0.004(2) O3 0.044(2) 0.045(2) 0.0352(19) -0.0062(16) -0.0002(16) -0.0015(17) N3 0.055(3) 0.042(3) 0.039(2) 0.008(2) 0.017(2) 0.000(2) C3 0.041(3) 0.029(3) 0.037(3) 0.002(2) 0.016(2) 0.007(2) O4 0.0398(19) 0.038(2) 0.0312(18) 0.0001(16) 0.0022(15) -0.0032(16) N4 0.053(3) 0.089(4) 0.044(3) -0.018(3) 0.009(2) 0.020(3) C4 0.047(3) 0.034(3) 0.022(2) -0.001(2) 0.006(2) -0.003(2) O5 0.043(2) 0.042(2) 0.0283(18) 0.0029(16) -0.0033(15) -0.0017(17) C5 0.033(3) 0.032(3) 0.029(3) 0.004(2) 0.003(2) -0.002(2) O6 0.041(2) 0.038(2) 0.0282(18) 0.0088(15) 0.0007(16) -0.0028(17) C6 0.041(3) 0.028(3) 0.022(2) 0.0015(19) 0.012(2) -0.008(2) O7 0.039(2) 0.048(2) 0.0325(18) 0.0134(16) 0.0052(16) 0.0102(16) C7 0.037(3) 0.035(3) 0.033(3) 0.004(2) 0.016(2) -0.003(2) O8 0.051(2) 0.059(2) 0.037(2) 0.0197(17) 0.0192(18) 0.0062(19) C8 0.049(3) 0.051(3) 0.030(3) 0.008(2) 0.020(2) -0.004(2) O9 0.041(2) 0.044(2) 0.040(2) 0.0117(17) 0.0167(17) 0.0021(17) C9 0.087(5) 0.082(5) 0.058(4) 0.008(3) 0.041(4) -0.016(4) O10 0.050(2) 0.038(2) 0.049(2) 0.0004(16) 0.030(2) 0.0018(19) C10 0.120(6) 0.097(5) 0.069(4) 0.009(4) 0.045(4) -0.029(5) O11 0.052(2) 0.039(2) 0.050(2) -0.0047(17) 0.0282(18) 0.0040(17) C11 0.033(3) 0.036(3) 0.026(2) 0.000(2) 0.010(2) -0.001(2) O12 0.044(2) 0.033(2) 0.0426(19) -0.0005(15) 0.0138(17) 0.0036(16) C12 0.027(2) 0.039(3) 0.026(2) -0.002(2) 0.012(2) 0.000(2) C13 0.029(3) 0.034(3) 0.026(2) -0.003(2) 0.007(2) -0.003(2) C14 0.033(3) 0.040(3) 0.018(2) 0.001(2) 0.0035(19) 0.006(2) C15 0.037(3) 0.029(3) 0.023(2) 0.005(2) 0.008(2) 0.003(2) C16 0.027(2) 0.034(3) 0.026(2) 0.003(2) 0.012(2) 0.001(2) C17 0.039(3) 0.029(3) 0.022(2) 0.0028(19) 0.008(2) 0.002(2) C18 0.047(3) 0.045(3) 0.030(3) -0.007(2) 0.014(2) 0.002(2) C19 0.066(4) 0.081(4) 0.043(3) -0.004(3) 0.019(3) 0.017(3) C20 0.101(5) 0.136(6) 0.043(4) -0.004(4) 0.031(4) 0.040(5) C21 0.042(3) 0.027(3) 0.024(2) 0.0011(19) 0.013(2) -0.003(2) C22 0.036(3) 0.023(2) 0.022(2) -0.0010(19) 0.006(2) -0.005(2) C23 0.041(3) 0.028(3) 0.025(2) 0.006(2) 0.004(2) 0.006(2) C24 0.041(3) 0.034(3) 0.025(2) 0.005(2) 0.012(2) -0.001(2) C25 0.031(3) 0.032(3) 0.030(2) 0.001(2) 0.010(2) -0.003(2) C26 0.034(3) 0.022(2) 0.024(2) -0.0018(19) 0.006(2) -0.003(2) C27 0.030(2) 0.033(3) 0.028(2) 0.005(2) 0.007(2) 0.000(2) C28 0.050(3) 0.035(3) 0.022(2) 0.002(2) 0.006(2) 0.000(2) C29 0.061(3) 0.054(3) 0.026(3) -0.002(2) 0.003(2) 0.005(3) C30 0.084(4) 0.100(5) 0.034(3) 0.002(3) 0.007(3) 0.007(4) C31 0.032(3) 0.034(3) 0.025(2) 0.001(2) 0.008(2) 0.002(2) C32 0.033(3) 0.029(3) 0.023(2) 0.002(2) 0.007(2) 0.004(2) C33 0.040(3) 0.028(3) 0.027(2) 0.006(2) 0.009(2) -0.001(2) C34 0.037(3) 0.031(3) 0.031(3) 0.000(2) 0.013(2) 0.003(2) C35 0.041(3) 0.022(2) 0.026(2) -0.0012(19) 0.006(2) 0.006(2) C36 0.030(2) 0.031(3) 0.019(2) -0.0005(19) 0.0029(19) 0.004(2) C37 0.035(3) 0.032(3) 0.021(2) 0.0020(19) 0.008(2) 0.004(2) C38 0.051(3) 0.037(3) 0.024(2) 0.002(2) 0.010(2) 0.004(2) C39 0.058(3) 0.053(4) 0.030(3) 0.010(2) 0.006(3) 0.003(3) C40 0.082(5) 0.120(6) 0.048(4) 0.005(4) 0.009(3) 0.000(4) C41 0.078(4) 0.061(4) 0.032(3) -0.008(3) 0.011(3) 0.016(3) C42 0.078(4) 0.055(4) 0.036(3) -0.006(3) 0.009(3) 0.013(3) C43 0.048(3) 0.044(3) 0.025(3) -0.002(2) 0.003(2) -0.009(3) C44 0.049(3) 0.072(4) 0.037(3) -0.003(3) 0.016(3) -0.012(3) C45 0.052(3) 0.069(4) 0.026(3) -0.002(3) 0.003(3) -0.007(3) C46 0.047(3) 0.055(3) 0.034(3) -0.005(2) 0.008(3) -0.004(3) C47 0.047(3) 0.051(3) 0.031(3) -0.005(2) 0.013(2) 0.003(3) C48 0.050(3) 0.049(3) 0.027(3) -0.003(2) 0.010(2) -0.007(3) C49 0.049(3) 0.106(5) 0.026(3) -0.010(3) 0.009(3) -0.029(3) C50 0.051(3) 0.102(5) 0.031(3) -0.005(3) 0.018(3) -0.021(3) C51 0.060(4) 0.058(4) 0.040(3) 0.017(3) 0.016(3) 0.008(3) C52 0.050(3) 0.044(3) 0.044(3) 0.015(3) 0.015(3) 0.010(3) C53 0.041(3) 0.032(3) 0.041(3) 0.002(2) 0.010(2) 0.000(2) C54 0.055(3) 0.042(3) 0.034(3) 0.002(2) 0.014(2) 0.003(3) C55 0.057(3) 0.038(3) 0.049(3) -0.005(3) 0.012(3) 0.009(3) C56 0.042(3) 0.040(3) 0.037(3) 0.000(2) 0.006(2) 0.004(2) C61 0.164(11) 0.324(19) 0.142(10) -0.043(11) 0.003(9) -0.013(11) C62 0.110(7) 0.113(7) 0.088(6) -0.018(5) 0.057(6) -0.005(5) C63 0.193(11) 0.310(17) 0.239(13) -0.165(12) 0.168(11) -0.138(11) O64 0.156(6) 0.158(6) 0.160(6) 0.040(5) 0.081(5) 0.022(4) C57A 0.083(11) 0.049(9) 0.031(7) 0.000(7) 0.014(7) 0.030(7) C58A 0.098(15) 0.083(13) 0.029(8) 0.011(9) 0.018(9) 0.037(11) C59A 0.069(8) 0.056(8) 0.040(7) 0.008(6) 0.026(6) 0.023(7) C60A 0.048(7) 0.041(7) 0.049(7) 0.011(5) 0.034(6) 0.009(5) C57B 0.042(8) 0.109(13) 0.028(7) -0.002(8) 0.007(6) 0.019(8) C58B 0.045(10) 0.104(15) 0.038(7) -0.011(10) 0.008(7) 0.037(10) C59B 0.076(10) 0.130(14) 0.074(10) -0.059(10) 0.000(8) 0.030(10) C60B 0.078(10) 0.109(12) 0.052(8) -0.024(8) 0.006(7) 0.040(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.390(5) . ? N1 C41 1.324(6) . ? N1 C45 1.328(6) . ? C1 C2 1.376(6) . ? C1 C6 1.405(6) . ? O2 C4 1.381(5) . ? N2 C50 1.309(6) . ? N2 C46 1.338(6) . ? C2 C3 1.398(6) . ? C2 C37 1.525(6) . ? O3 C5 1.378(5) . ? N3 C55 1.321(6) . ? N3 C51 1.328(6) . ? C3 C4 1.362(6) . ? O4 C13 1.368(5) . ? N4 C58B 1.173(17) . ? N4 C58A 1.317(18) . ? N4 C59A 1.396(11) . ? N4 C59B 1.414(13) . ? C4 C5 1.377(6) . ? O5 C14 1.380(5) . ? C5 C6 1.410(6) . ? O6 C15 1.378(5) . ? C6 C7 1.499(6) . ? O7 C23 1.381(5) . ? C7 C12 1.538(6) . ? C7 C8 1.547(6) . ? O8 C24 1.391(5) . ? C8 C9 1.545(7) . ? O9 C25 1.388(5) . ? C9 C10 1.426(8) . ? O10 C33 1.380(5) . ? O11 C34 1.375(5) . ? C11 C16 1.384(6) . ? C11 C12 1.386(6) . ? O12 C35 1.386(5) . ? C12 C13 1.387(6) . ? C13 C14 1.397(6) . ? C14 C15 1.373(6) . ? C15 C16 1.406(5) . ? C16 C17 1.523(6) . ? C17 C22 1.518(6) . ? C17 C18 1.536(6) . ? C18 C19 1.493(7) . ? C19 C20 1.516(7) . ? C21 C22 1.383(6) . ? C21 C26 1.389(6) . ? C22 C23 1.407(6) . ? C23 C24 1.374(6) . ? C24 C25 1.375(6) . ? C25 C26 1.399(6) . ? C26 C27 1.522(6) . ? C27 C32 1.516(6) . ? C27 C28 1.543(6) . ? C28 C29 1.497(6) . ? C29 C30 1.514(7) . ? C31 C36 1.378(6) . ? C31 C32 1.383(6) . ? C32 C33 1.399(6) . ? C33 C34 1.390(6) . ? C34 C35 1.386(6) . ? C35 C36 1.394(6) . ? C36 C37 1.530(6) . ? C37 C38 1.540(6) . ? C38 C39 1.511(6) . ? C39 C40 1.492(8) . ? C41 C42 1.394(7) . ? C42 C43 1.379(7) . ? C43 C44 1.375(7) . ? C43 C48 1.480(6) . ? C44 C45 1.380(6) . ? C46 C47 1.377(6) . ? C47 C48 1.382(6) . ? C48 C49 1.389(7) . ? C49 C50 1.377(6) . ? C51 C52 1.373(7) . ? C52 C53 1.398(6) . ? C53 C54 1.394(6) . ? C53 C56 1.504(6) . ? C54 C55 1.384(6) . ? C56 C57A 1.309(13) . ? C56 C60A 1.386(11) . ? C56 C57B 1.415(13) . ? C56 C60B 1.426(14) . ? C61 C62 1.449(11) . ? C62 O64 1.222(8) . ? C62 C63 1.374(11) . ? C57A C58A 1.36(2) . ? C59A C60A 1.369(14) . ? C57B C58B 1.38(2) . ? C59B C60B 1.355(17) . ? 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 C41 N1 C45 116.8(4) . . ? C2 C1 C6 124.2(4) . . ? C50 N2 C46 115.6(4) . . ? C1 C2 C3 117.8(4) . . ? C1 C2 C37 121.8(4) . . ? C3 C2 C37 120.5(4) . . ? C55 N3 C51 115.7(4) . . ? C4 C3 O1 121.6(4) . . ? C4 C3 C2 120.2(4) . . ? O1 C3 C2 118.2(4) . . ? C58B N4 C58A 40.4(9) . . ? C58B N4 C59A 101.1(11) . . ? C58A N4 C59A 113.6(10) . . ? C58B N4 C59B 120.8(11) . . ? C58A N4 C59B 96.5(10) . . ? C59A N4 C59B 52.8(8) . . ? C3 C4 C5 121.4(4) . . ? C3 C4 O2 118.3(4) . . ? C5 C4 O2 120.3(4) . . ? C4 C5 O3 114.8(4) . . ? C4 C5 C6 121.1(4) . . ? O3 C5 C6 124.1(4) . . ? C1 C6 C5 115.2(4) . . ? C1 C6 C7 123.4(4) . . ? C5 C6 C7 121.3(4) . . ? C6 C7 C12 110.0(3) . . ? C6 C7 C8 114.1(4) . . ? C12 C7 C8 111.6(4) . . ? C9 C8 C7 114.6(4) . . ? C10 C9 C8 115.7(5) . . ? C16 C11 C12 124.0(4) . . ? C11 C12 C13 117.9(4) . . ? C11 C12 C7 121.2(4) . . ? C13 C12 C7 120.8(4) . . ? O4 C13 C12 119.2(4) . . ? O4 C13 C14 121.2(4) . . ? C12 C13 C14 119.6(4) . . ? C15 C14 O5 122.4(4) . . ? C15 C14 C13 121.3(4) . . ? O5 C14 C13 116.3(4) . . ? C14 C15 O6 116.2(4) . . ? C14 C15 C16 120.3(4) . . ? O6 C15 C16 123.5(4) . . ? C11 C16 C15 116.8(4) . . ? C11 C16 C17 121.6(4) . . ? C15 C16 C17 121.6(4) . . ? C22 C17 C16 111.4(3) . . ? C22 C17 C18 112.6(4) . . ? C16 C17 C18 112.6(4) . . ? C19 C18 C17 116.0(4) . . ? C18 C19 C20 113.8(5) . . ? C22 C21 C26 124.4(4) . . ? C21 C22 C23 117.0(4) . . ? C21 C22 C17 122.3(4) . . ? C23 C22 C17 120.7(4) . . ? C24 C23 O7 121.0(4) . . ? C24 C23 C22 119.9(4) . . ? O7 C23 C22 119.1(4) . . ? C23 C24 C25 121.4(4) . . ? C23 C24 O8 118.3(4) . . ? C25 C24 O8 120.3(4) . . ? C24 C25 O9 115.7(4) . . ? C24 C25 C26 120.9(4) . . ? O9 C25 C26 123.4(4) . . ? C21 C26 C25 116.3(4) . . ? C21 C26 C27 123.2(4) . . ? C25 C26 C27 120.5(4) . . ? C32 C27 C26 112.5(3) . . ? C32 C27 C28 113.2(3) . . ? C26 C27 C28 112.0(3) . . ? C29 C28 C27 113.3(4) . . ? C28 C29 C30 112.5(4) . . ? C36 C31 C32 124.0(4) . . ? C31 C32 C33 117.3(4) . . ? C31 C32 C27 122.2(4) . . ? C33 C32 C27 120.5(4) . . ? O10 C33 C34 121.2(4) . . ? O10 C33 C32 118.5(4) . . ? C34 C33 C32 120.3(4) . . ? O11 C34 C35 122.0(4) . . ? O11 C34 C33 117.9(4) . . ? C35 C34 C33 120.1(4) . . ? O12 C35 C34 115.5(4) . . ? O12 C35 C36 123.8(4) . . ? C34 C35 C36 120.7(4) . . ? C31 C36 C35 117.4(4) . . ? C31 C36 C37 121.5(4) . . ? C35 C36 C37 121.1(4) . . ? C2 C37 C36 110.9(3) . . ? C2 C37 C38 113.4(4) . . ? C36 C37 C38 111.2(3) . . ? C39 C38 C37 114.5(4) . . ? C40 C39 C38 113.4(4) . . ? N1 C41 C42 124.0(5) . . ? C43 C42 C41 118.8(5) . . ? C44 C43 C42 116.8(4) . . ? C44 C43 C48 121.0(5) . . ? C42 C43 C48 122.2(5) . . ? C43 C44 C45 120.8(5) . . ? N1 C45 C44 122.7(5) . . ? N2 C46 C47 124.5(5) . . ? C46 C47 C48 119.0(5) . . ? C47 C48 C49 116.8(4) . . ? C47 C48 C43 122.0(4) . . ? C49 C48 C43 121.2(4) . . ? C50 C49 C48 119.1(5) . . ? N2 C50 C49 125.0(5) . . ? N3 C51 C52 125.1(5) . . ? C51 C52 C53 118.8(5) . . ? C54 C53 C52 116.7(4) . . ? C54 C53 C56 121.2(4) . . ? C52 C53 C56 122.1(4) . . ? C55 C54 C53 118.9(4) . . ? N3 C55 C54 124.7(5) . . ? C57A C56 C60A 119.8(8) . . ? C57A C56 C57B 40.4(6) . . ? C60A C56 C57B 99.9(8) . . ? C57A C56 C60B 97.2(9) . . ? C60A C56 C60B 50.5(7) . . ? C57B C56 C60B 112.5(8) . . ? C57A C56 C53 121.7(7) . . ? C60A C56 C53 118.4(6) . . ? C57B C56 C53 125.2(7) . . ? C60B C56 C53 122.0(6) . . ? O64 C62 C63 119.7(10) . . ? O64 C62 C61 123.5(10) . . ? C63 C62 C61 116.8(10) . . ? C56 C57A C58A 118.6(12) . . ? N4 C58A C57A 126.7(15) . . ? C60A C59A N4 121.9(10) . . ? C59A C60A C56 119.0(9) . . ? C58B C57B C56 120.8(12) . . ? N4 C58B C57B 124.3(15) . . ? C60B C59B N4 118.9(12) . . ? C59B C60B C56 121.4(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.19 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.656 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.065