Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_als500 _database_code_CSD 170259 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Rebek' _publ_contact_author_name 'Prof Rebek' _publ_contact_author_address ; The Skaggs Institute for Chem Biol The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 UNITED STATES OF AMERICA ; _publ_contact_author_email 'LUNDGREN@SCRIPPS.EDU' _publ_section_title ; Hydrogen-bonded capsules in polar, protic solvents ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'resorcinarene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H59 N3 O17' _chemical_formula_weight 925.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4558(10) _cell_length_b 11.6273(10) _cell_length_c 18.6627(16) _cell_angle_alpha 102.785(2) _cell_angle_beta 90.042(2) _cell_angle_gamma 102.881(2) _cell_volume 2360.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.100 _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 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 ? _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 21800 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 28.06 _reflns_number_total 11082 _reflns_number_gt 7603 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1159P)^2^+0.2774P] 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 11082 _refine_ls_number_parameters 639 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.2055 _refine_ls_wR_factor_gt 0.1786 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C1 C 0.40566(19) 1.0746(2) 0.21298(11) 0.0186(4) Uani 1 1 d . . . H1 H 0.4003 0.9968 0.2286 0.022 Uiso 1 1 calc R . . C1A C 0.41017(19) 1.0460(2) 0.12897(12) 0.0207(5) Uani 1 1 d . . . H1A1 H 0.4087 1.1200 0.1114 0.025 Uiso 1 1 calc R . . H1A2 H 0.4868 1.0233 0.1153 0.025 Uiso 1 1 calc R . . C1B C 0.3074(2) 0.9446(2) 0.09032(14) 0.0310(6) Uani 1 1 d . . . H1B1 H 0.2305 0.9658 0.1051 0.037 Uiso 1 1 calc R . . H1B2 H 0.3105 0.8695 0.1063 0.037 Uiso 1 1 calc R . . C1C C 0.3114(3) 0.9209(3) 0.00709(15) 0.0467(8) Uani 1 1 d . . . H1C1 H 0.3053 0.9940 -0.0092 0.070 Uiso 1 1 calc R . . H1C2 H 0.2442 0.8541 -0.0153 0.070 Uiso 1 1 calc R . . H1C3 H 0.3871 0.8994 -0.0079 0.070 Uiso 1 1 calc R . . C2 C 0.51755(19) 1.1625(2) 0.25175(12) 0.0194(4) Uani 1 1 d . . . C3 C 0.55371(19) 1.15827(19) 0.32256(12) 0.0190(4) Uani 1 1 d . . . C4 C 0.6519(2) 1.2411(2) 0.35988(11) 0.0192(4) Uani 1 1 d . . . C5 C 0.71726(19) 1.3312(2) 0.32818(12) 0.0192(4) Uani 1 1 d . . . C6 C 0.68494(19) 1.3372(2) 0.25723(12) 0.0180(4) Uani 1 1 d . . . C7 C 0.5855(2) 1.2530(2) 0.22108(12) 0.0201(4) Uani 1 1 d . . . H7 H 0.5625 1.2572 0.1730 0.024 Uiso 1 1 calc R . . C8 C 0.76029(19) 1.4345(2) 0.22289(12) 0.0193(4) Uani 1 1 d . . . H8 H 0.8456 1.4446 0.2398 0.023 Uiso 1 1 calc R . . C8A C 0.7543(2) 1.3980(2) 0.13844(12) 0.0234(5) Uani 1 1 d . . . H8A1 H 0.7702 1.3160 0.1229 0.028 Uiso 1 1 calc R . . H8A2 H 0.6722 1.3938 0.1198 0.028 Uiso 1 1 calc R . . C8B C 0.8433(2) 1.4850(2) 0.10359(14) 0.0308(6) Uani 1 1 d . . . H8B1 H 0.8307 1.5679 0.1210 0.037 Uiso 1 1 calc R . . H8B2 H 0.9259 1.4855 0.1196 0.037 Uiso 1 1 calc R . . C8C C 0.8305(3) 1.4506(3) 0.02075(15) 0.0481(8) Uani 1 1 d . . . H8C1 H 0.8468 1.3701 0.0031 0.072 Uiso 1 1 calc R . . H8C2 H 0.8876 1.5100 0.0006 0.072 Uiso 1 1 calc R . . H8C3 H 0.7486 1.4492 0.0046 0.072 Uiso 1 1 calc R . . C9 C 0.72813(19) 1.5565(2) 0.25075(12) 0.0196(4) Uani 1 1 d . . . C10 C 0.80370(19) 1.6510(2) 0.30058(12) 0.0201(4) Uani 1 1 d . . . C11 C 0.7734(2) 1.7631(2) 0.32201(12) 0.0213(5) Uani 1 1 d . . . C12 C 0.6697(2) 1.7825(2) 0.29321(12) 0.0216(5) Uani 1 1 d . . . C13 C 0.59220(19) 1.6896(2) 0.24318(12) 0.0194(4) Uani 1 1 d . . . C14 C 0.6228(2) 1.5779(2) 0.22456(12) 0.0215(5) Uani 1 1 d . . . H14 H 0.5691 1.5128 0.1923 0.026 Uiso 1 1 calc R . . C15 C 0.4796(2) 1.7087(2) 0.20858(12) 0.0212(5) Uani 1 1 d . . . H15 H 0.4825 1.7975 0.2226 0.025 Uiso 1 1 calc R . . C15A C 0.4769(2) 1.6728(2) 0.12463(13) 0.0253(5) Uani 1 1 d . . . H15A H 0.4800 1.5865 0.1092 0.030 Uiso 1 1 calc R . . H15B H 0.4000 1.6813 0.1046 0.030 Uiso 1 1 calc R . . C15B C 0.5799(2) 1.7485(3) 0.09158(15) 0.0336(6) Uani 1 1 d . . . H15C H 0.5752 1.8346 0.1053 0.040 Uiso 1 1 calc R . . H15D H 0.6569 1.7422 0.1126 0.040 Uiso 1 1 calc R . . C15C C 0.5775(3) 1.7085(3) 0.00865(16) 0.0476(8) Uani 1 1 d . . . H15E H 0.5838 1.6239 -0.0052 0.071 Uiso 1 1 calc R . . H15F H 0.6450 1.7597 -0.0100 0.071 Uiso 1 1 calc R . . H15G H 0.5020 1.7161 -0.0125 0.071 Uiso 1 1 calc R . . C16 C 0.36870(19) 1.64465(19) 0.24131(12) 0.0190(4) Uani 1 1 d . . . C17 C 0.3394(2) 1.6977(2) 0.31188(12) 0.0212(5) Uani 1 1 d . . . C18 C 0.2405(2) 1.6432(2) 0.34442(12) 0.0206(5) Uani 1 1 d . . . C19 C 0.17006(19) 1.5314(2) 0.30863(12) 0.0205(5) Uani 1 1 d . . . C20 C 0.19640(19) 1.4741(2) 0.23847(12) 0.0186(4) Uani 1 1 d . . . C21 C 0.2953(2) 1.5339(2) 0.20642(12) 0.0194(4) Uani 1 1 d . . . H21 H 0.3132 1.4969 0.1583 0.023 Uiso 1 1 calc R . . C22 C 0.12121(19) 1.3499(2) 0.20110(12) 0.0196(4) Uani 1 1 d . . . H22 H 0.0364 1.3497 0.2140 0.024 Uiso 1 1 calc R . . C22A C 0.1218(2) 1.3211(2) 0.11722(13) 0.0250(5) Uani 1 1 d . . . H22A H 0.1019 1.3886 0.0991 0.030 Uiso 1 1 calc R . . H22B H 0.2035 1.3149 0.1023 0.030 Uiso 1 1 calc R . . C22B C 0.0333(2) 1.2038(3) 0.08132(15) 0.0359(6) Uani 1 1 d . . . H22C H 0.0532 1.1363 0.0994 0.043 Uiso 1 1 calc R . . H22D H -0.0484 1.2099 0.0963 0.043 Uiso 1 1 calc R . . C22C C 0.0337(3) 1.1752(3) -0.00128(16) 0.0476(8) Uani 1 1 d . . . H22E H 0.0106 1.2400 -0.0198 0.071 Uiso 1 1 calc R . . H22F H -0.0236 1.0983 -0.0214 0.071 Uiso 1 1 calc R . . H22G H 0.1142 1.1687 -0.0166 0.071 Uiso 1 1 calc R . . C23 C 0.1573(2) 1.2522(2) 0.23314(12) 0.0223(5) Uani 1 1 d . . . C24 C 0.0896(2) 1.2033(2) 0.28533(13) 0.0248(5) Uani 1 1 d . . . C25 C 0.1239(2) 1.1151(2) 0.31522(13) 0.0249(5) Uani 1 1 d . . . C26 C 0.2248(2) 1.0746(2) 0.29177(12) 0.0217(5) Uani 1 1 d . . . C27 C 0.2942(2) 1.1203(2) 0.23916(12) 0.0205(4) Uani 1 1 d . . . C28 C 0.2607(2) 1.2115(2) 0.21202(12) 0.0204(4) Uani 1 1 d . . . H28 H 0.3099 1.2470 0.1781 0.025 Uiso 1 1 calc R . . CN1 C 0.4416(3) 1.4434(3) 0.36170(16) 0.0551(9) Uani 1 1 d . . . HN1A H 0.3688 1.3832 0.3404 0.083 Uiso 1 1 calc R . . HN1B H 0.5025 1.4021 0.3734 0.083 Uiso 1 1 calc R . . HN1C H 0.4722 1.4922 0.3263 0.083 Uiso 1 1 calc R . . CN2 C 0.4140(3) 1.5212(3) 0.42808(15) 0.0411(7) Uani 1 1 d . . . O1 O 0.49466(14) 1.07141(15) 0.35725(9) 0.0246(4) Uani 1 1 d . . . H1A H 0.4223 1.0496 0.3422 0.037 Uiso 1 1 calc R . . O2 O 0.68657(15) 1.23056(15) 0.42900(8) 0.0237(4) Uani 1 1 d . . . H2 H 0.6692 1.2862 0.4613 0.036 Uiso 1 1 calc R . . O03 O 0.92966(17) 1.38867(19) 0.48405(10) 0.0398(5) Uani 1 1 d . . . O3 O 0.81309(14) 1.41579(15) 0.36497(9) 0.0235(4) Uani 1 1 d . . . H3 H 0.8366 1.3917 0.4005 0.035 Uiso 1 1 calc R . . O4 O 0.91135(14) 1.64368(15) 0.32972(9) 0.0254(4) Uani 1 1 d . . . H4 H 0.9050 1.5747 0.3384 0.038 Uiso 1 1 calc R . . O5 O 0.85030(15) 1.85170(15) 0.37120(9) 0.0268(4) Uani 1 1 d . . . H5 H 0.8266 1.9164 0.3777 0.040 Uiso 1 1 calc R . . O6 O 0.65151(15) 1.89819(14) 0.31534(10) 0.0271(4) Uani 1 1 d . . . H6 H 0.5808 1.8947 0.3282 0.041 Uiso 1 1 calc R . . O7 O 0.41143(15) 1.80587(15) 0.34792(9) 0.0283(4) Uani 1 1 d . . . H7A H 0.3898 1.8245 0.3911 0.042 Uiso 1 1 calc R . . O8 O 0.21592(15) 1.69931(15) 0.41335(8) 0.0251(4) Uani 1 1 d . . . H8A H 0.1783 1.7524 0.4102 0.038 Uiso 1 1 calc R . . O9 O 0.07526(15) 1.48558(15) 0.34714(9) 0.0260(4) Uani 1 1 d . . . H9 H 0.0526 1.4104 0.3306 0.039 Uiso 1 1 calc R . . O10 O -0.01194(15) 1.24206(16) 0.31093(10) 0.0306(4) Uani 1 1 d . . . H10 H -0.0734 1.1904 0.2912 0.046 Uiso 1 1 calc R . . O010 O -0.14280(15) 1.09060(15) 0.43307(9) 0.0261(4) Uani 1 1 d . . . O11 O 0.06161(17) 1.06732(17) 0.36744(11) 0.0343(4) Uani 1 1 d . . . H11 H 0.0009 1.0965 0.3760 0.051 Uiso 1 1 calc R . . O12 O 0.25185(14) 0.98463(15) 0.32188(9) 0.0257(4) Uani 1 1 d . . . H12 H 0.3067 0.9578 0.2988 0.039 Uiso 1 1 calc R . . O012 O 0.09079(17) 0.86820(17) 0.41648(10) 0.0357(4) Uani 1 1 d . . . O020 O -0.18545(19) 1.0637(2) 0.24004(12) 0.0477(5) Uani 1 1 d . . . N1 N 0.3905(3) 1.5816(3) 0.47976(14) 0.0572(8) Uani 1 1 d . . . N3 N -0.0569(3) 0.8789(3) 0.18897(16) 0.0578(8) Uani 1 1 d . . . CN5 C 0.0085(3) 0.8193(3) 0.19399(15) 0.0406(7) Uani 1 1 d . . . CN6 C 0.0911(3) 0.7449(3) 0.20027(18) 0.0455(7) Uani 1 1 d . . . HN6A H 0.1661 0.7960 0.2254 0.068 Uiso 1 1 calc R . . HN6B H 0.1073 0.7027 0.1511 0.068 Uiso 1 1 calc R . . HN6C H 0.0560 0.6853 0.2287 0.068 Uiso 1 1 calc R . . N2 N 0.6478(18) 1.8287(15) 0.5116(8) 0.099(5) Uani 0.482(12) 1 d P A 1 CN3 C 0.7865(16) 1.6841(11) 0.4953(8) 0.055(3) Uani 0.482(12) 1 d P A 1 HN3A H 0.8057 1.6686 0.5429 0.082 Uiso 0.482(12) 1 calc PR A 1 HN3B H 0.8605 1.7207 0.4746 0.082 Uiso 0.482(12) 1 calc PR A 1 HN3C H 0.7477 1.6075 0.4616 0.082 Uiso 0.482(12) 1 calc PR A 1 CN4 C 0.6995(9) 1.7728(11) 0.5058(5) 0.037(2) Uani 0.482(12) 1 d P A 1 N4 N 0.8619(8) 1.6855(7) 0.5121(4) 0.065(2) Uani 0.518(12) 1 d P A 2 CN7 C 0.7833(11) 1.7305(10) 0.5101(5) 0.046(3) Uani 0.518(12) 1 d P A 2 CN8 C 0.6689(6) 1.7871(5) 0.5006(4) 0.148(19) Uani 0.518(12) 1 d P A 2 HN8A H 0.6962 1.8743 0.5037 0.221 Uiso 0.518(12) 1 calc PR A 2 HN8B H 0.6140 1.7738 0.5398 0.221 Uiso 0.518(12) 1 calc PR A 2 HN8C H 0.6272 1.7476 0.4527 0.221 Uiso 0.518(12) 1 calc PR A 2 H1X H -0.2138 1.1277 0.4454 0.097(15) Uiso 1 1 d R . . H1Y H -0.1431 1.0919 0.4876 0.091(14) Uiso 1 1 d R . . O07 O 0.3872(5) 1.9330(4) 0.4816(2) 0.0631(13) Uiso 0.50 1 d PR . . O07A O 0.4618(5) 1.9654(5) 0.4850(3) 0.0523(19) Uiso 0.30 1 d PR . . 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 C1 0.0185(10) 0.0168(11) 0.0194(10) 0.0036(8) -0.0005(8) 0.0020(8) C1A 0.0185(11) 0.0186(11) 0.0228(11) 0.0026(9) 0.0006(8) 0.0021(9) C1B 0.0283(13) 0.0305(14) 0.0263(12) -0.0032(10) 0.0010(10) 0.0002(11) C1C 0.0451(17) 0.0520(19) 0.0272(14) -0.0084(13) -0.0008(12) -0.0041(14) C2 0.0174(10) 0.0203(11) 0.0202(10) 0.0031(8) -0.0012(8) 0.0052(9) C3 0.0192(11) 0.0160(10) 0.0238(11) 0.0077(8) 0.0030(8) 0.0052(8) C4 0.0214(11) 0.0230(11) 0.0154(10) 0.0045(8) -0.0007(8) 0.0096(9) C5 0.0177(10) 0.0191(11) 0.0208(10) 0.0025(8) -0.0016(8) 0.0063(9) C6 0.0178(10) 0.0171(11) 0.0197(10) 0.0039(8) 0.0020(8) 0.0056(8) C7 0.0223(11) 0.0213(11) 0.0187(10) 0.0059(8) -0.0011(8) 0.0076(9) C8 0.0174(10) 0.0188(11) 0.0209(10) 0.0030(8) -0.0006(8) 0.0041(9) C8A 0.0255(12) 0.0209(12) 0.0228(11) 0.0044(9) 0.0016(9) 0.0034(9) C8B 0.0300(13) 0.0327(14) 0.0303(13) 0.0124(11) 0.0039(10) 0.0032(11) C8C 0.057(2) 0.057(2) 0.0303(15) 0.0196(14) 0.0098(13) 0.0031(16) C9 0.0201(11) 0.0204(11) 0.0189(10) 0.0060(8) 0.0032(8) 0.0046(9) C10 0.0170(10) 0.0214(11) 0.0222(11) 0.0066(9) 0.0010(8) 0.0035(9) C11 0.0215(11) 0.0162(11) 0.0238(11) 0.0033(9) 0.0006(9) 0.0008(9) C12 0.0223(11) 0.0182(11) 0.0248(11) 0.0054(9) 0.0042(9) 0.0051(9) C13 0.0185(10) 0.0186(11) 0.0224(11) 0.0076(9) 0.0034(8) 0.0042(9) C14 0.0210(11) 0.0182(11) 0.0237(11) 0.0045(9) -0.0003(8) 0.0012(9) C15 0.0205(11) 0.0192(11) 0.0249(11) 0.0072(9) 0.0015(9) 0.0046(9) C15A 0.0249(12) 0.0293(13) 0.0246(12) 0.0118(10) 0.0039(9) 0.0068(10) C15B 0.0310(14) 0.0355(15) 0.0372(14) 0.0173(12) 0.0069(11) 0.0046(11) C15C 0.0479(18) 0.064(2) 0.0372(16) 0.0262(15) 0.0162(13) 0.0107(16) C16 0.0197(11) 0.0155(11) 0.0241(11) 0.0072(8) 0.0004(8) 0.0059(9) C17 0.0194(11) 0.0202(11) 0.0239(11) 0.0037(9) -0.0006(8) 0.0055(9) C18 0.0235(11) 0.0222(12) 0.0178(10) 0.0024(9) 0.0023(8) 0.0110(9) C19 0.0196(11) 0.0222(11) 0.0235(11) 0.0100(9) 0.0031(8) 0.0075(9) C20 0.0190(10) 0.0184(11) 0.0198(10) 0.0057(8) 0.0001(8) 0.0058(9) C21 0.0235(11) 0.0191(11) 0.0178(10) 0.0053(8) 0.0022(8) 0.0083(9) C22 0.0163(10) 0.0198(11) 0.0227(11) 0.0054(9) 0.0028(8) 0.0035(9) C22A 0.0224(11) 0.0263(13) 0.0256(12) 0.0044(9) -0.0036(9) 0.0056(10) C22B 0.0326(14) 0.0341(15) 0.0338(14) -0.0018(11) -0.0073(11) 0.0017(12) C22C 0.0479(18) 0.0505(19) 0.0355(15) -0.0055(13) -0.0128(13) 0.0081(15) C23 0.0217(11) 0.0187(11) 0.0246(11) 0.0030(9) 0.0001(9) 0.0027(9) C24 0.0235(12) 0.0202(12) 0.0295(12) 0.0039(9) 0.0058(9) 0.0041(9) C25 0.0250(12) 0.0221(12) 0.0264(12) 0.0068(9) 0.0078(9) 0.0013(9) C26 0.0238(11) 0.0190(11) 0.0208(11) 0.0053(9) 0.0002(9) 0.0009(9) C27 0.0208(11) 0.0179(11) 0.0201(10) 0.0009(8) -0.0013(8) 0.0027(9) C28 0.0203(11) 0.0204(11) 0.0197(10) 0.0054(8) 0.0023(8) 0.0019(9) CN1 0.081(2) 0.068(2) 0.0295(15) 0.0044(15) 0.0027(15) 0.052(2) CN2 0.0514(18) 0.0489(18) 0.0315(14) 0.0071(13) -0.0052(12) 0.0313(15) O1 0.0186(8) 0.0241(9) 0.0310(9) 0.0120(7) -0.0021(7) -0.0007(7) O2 0.0291(9) 0.0268(9) 0.0167(7) 0.0059(6) -0.0022(6) 0.0087(7) O03 0.0351(10) 0.0496(12) 0.0307(10) 0.0153(9) -0.0033(8) -0.0046(9) O3 0.0216(8) 0.0242(9) 0.0220(8) 0.0061(6) -0.0057(6) -0.0008(7) O4 0.0208(8) 0.0203(8) 0.0344(9) 0.0059(7) -0.0062(7) 0.0035(7) O5 0.0242(8) 0.0186(8) 0.0334(9) -0.0016(7) -0.0062(7) 0.0036(7) O6 0.0230(8) 0.0170(8) 0.0396(10) 0.0020(7) 0.0000(7) 0.0053(7) O7 0.0271(9) 0.0230(9) 0.0291(9) -0.0028(7) 0.0021(7) 0.0025(7) O8 0.0288(9) 0.0267(9) 0.0208(8) 0.0025(7) 0.0040(6) 0.0111(7) O9 0.0275(9) 0.0213(9) 0.0287(9) 0.0067(7) 0.0097(7) 0.0037(7) O10 0.0249(9) 0.0235(9) 0.0440(11) 0.0087(8) 0.0144(8) 0.0058(7) O010 0.0288(9) 0.0284(9) 0.0230(8) 0.0056(7) 0.0040(7) 0.0109(7) O11 0.0338(10) 0.0347(11) 0.0437(11) 0.0223(9) 0.0216(8) 0.0136(8) O12 0.0225(9) 0.0271(9) 0.0328(9) 0.0148(7) 0.0064(7) 0.0084(7) O012 0.0411(11) 0.0364(11) 0.0316(9) 0.0022(8) -0.0094(8) 0.0187(9) O020 0.0378(11) 0.0469(13) 0.0555(13) 0.0056(10) 0.0062(10) 0.0096(10) N1 0.082(2) 0.072(2) 0.0292(13) -0.0019(13) -0.0067(13) 0.0535(18) N3 0.0643(19) 0.065(2) 0.0471(16) 0.0084(14) 0.0096(14) 0.0243(17) CN5 0.0448(17) 0.0451(18) 0.0271(13) 0.0053(12) 0.0025(12) 0.0034(14) CN6 0.0410(17) 0.0464(18) 0.0488(18) 0.0171(14) -0.0041(13) 0.0032(14) N2 0.165(12) 0.066(7) 0.060(7) -0.020(5) -0.013(7) 0.049(8) CN3 0.062(7) 0.057(8) 0.040(7) -0.003(5) 0.002(5) 0.019(7) CN4 0.021(4) 0.062(7) 0.023(4) 0.009(4) 0.003(3) 0.001(3) N4 0.066(5) 0.076(5) 0.055(4) 0.010(3) 0.000(3) 0.026(4) CN7 0.051(6) 0.058(7) 0.018(4) 0.001(4) 0.012(3) -0.001(6) CN8 0.19(4) 0.12(3) 0.082(14) -0.015(15) 0.006(16) -0.04(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.516(3) . ? C1 C27 1.529(3) . ? C1 C1A 1.533(3) . ? C1A C1B 1.517(3) . ? C1B C1C 1.519(4) . ? C2 C7 1.394(3) . ? C2 C3 1.399(3) . ? C3 O1 1.372(3) . ? C3 C4 1.377(3) . ? C4 O2 1.388(2) . ? C4 C5 1.391(3) . ? C5 O3 1.365(3) . ? C5 C6 1.396(3) . ? C6 C7 1.386(3) . ? C6 C8 1.524(3) . ? C8 C9 1.525(3) . ? C8 C8A 1.536(3) . ? C8A C8B 1.522(3) . ? C8B C8C 1.507(4) . ? C9 C14 1.394(3) . ? C9 C10 1.394(3) . ? C10 O4 1.375(3) . ? C10 C11 1.397(3) . ? C11 O5 1.362(3) . ? C11 C12 1.387(3) . ? C12 O6 1.380(3) . ? C12 C13 1.397(3) . ? C13 C14 1.390(3) . ? C13 C15 1.523(3) . ? C15 C16 1.524(3) . ? C15 C15A 1.528(3) . ? C15A C15B 1.525(3) . ? C15B C15C 1.513(4) . ? C16 C21 1.391(3) . ? C16 C17 1.401(3) . ? C17 O7 1.370(3) . ? C17 C18 1.381(3) . ? C18 O8 1.368(3) . ? C18 C19 1.391(3) . ? C19 O9 1.376(3) . ? C19 C20 1.398(3) . ? C20 C21 1.399(3) . ? C20 C22 1.520(3) . ? C22 C22A 1.527(3) . ? C22 C23 1.526(3) . ? C22A C22B 1.522(3) . ? C22B C22C 1.503(4) . ? C23 C24 1.386(3) . ? C23 C28 1.397(3) . ? C24 O10 1.388(3) . ? C24 C25 1.396(3) . ? C25 O11 1.353(3) . ? C25 C26 1.379(3) . ? C26 O12 1.382(3) . ? C26 C27 1.387(3) . ? C27 C28 1.396(3) . ? CN1 CN2 1.444(4) . ? CN2 N1 1.132(4) . ? N3 CN5 1.145(4) . ? CN5 CN6 1.438(5) . ? N2 CN4 0.96(3) . ? CN3 CN4 1.571(17) . ? N4 CN7 1.143(15) . ? CN7 CN8 1.617(14) . ? O07 O07A 0.850(5) . ? O07A O07A 1.101(12) 2_696 ? 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 C2 C1 C27 110.11(17) . . ? C2 C1 C1A 113.22(18) . . ? C27 C1 C1A 112.35(17) . . ? C1B C1A C1 113.46(19) . . ? C1A C1B C1C 112.5(2) . . ? C7 C2 C3 117.11(19) . . ? C7 C2 C1 122.71(18) . . ? C3 C2 C1 120.13(19) . . ? O1 C3 C4 117.30(19) . . ? O1 C3 C2 121.87(19) . . ? C4 C3 C2 120.8(2) . . ? C3 C4 O2 118.62(19) . . ? C3 C4 C5 120.79(19) . . ? O2 C4 C5 120.57(19) . . ? O3 C5 C4 121.64(18) . . ? O3 C5 C6 118.32(19) . . ? C4 C5 C6 120.0(2) . . ? C7 C6 C5 117.9(2) . . ? C7 C6 C8 123.10(18) . . ? C5 C6 C8 118.99(19) . . ? C6 C7 C2 123.32(19) . . ? C6 C8 C9 111.29(18) . . ? C6 C8 C8A 112.73(18) . . ? C9 C8 C8A 111.75(17) . . ? C8B C8A C8 113.44(19) . . ? C8C C8B C8A 112.1(2) . . ? C14 C9 C10 117.9(2) . . ? C14 C9 C8 120.2(2) . . ? C10 C9 C8 121.82(19) . . ? O4 C10 C9 124.2(2) . . ? O4 C10 C11 115.81(19) . . ? C9 C10 C11 119.92(19) . . ? O5 C11 C12 122.0(2) . . ? O5 C11 C10 117.26(19) . . ? C12 C11 C10 120.7(2) . . ? O6 C12 C11 115.9(2) . . ? O6 C12 C13 123.4(2) . . ? C11 C12 C13 120.7(2) . . ? C14 C13 C12 117.4(2) . . ? C14 C13 C15 120.5(2) . . ? C12 C13 C15 122.11(19) . . ? C13 C14 C9 123.3(2) . . ? C16 C15 C13 109.93(17) . . ? C16 C15 C15A 113.61(19) . . ? C13 C15 C15A 111.61(19) . . ? C15B C15A C15 113.5(2) . . ? C15C C15B C15A 112.4(2) . . ? C21 C16 C17 117.0(2) . . ? C21 C16 C15 124.2(2) . . ? C17 C16 C15 118.71(19) . . ? O7 C17 C18 120.6(2) . . ? O7 C17 C16 118.2(2) . . ? C18 C17 C16 121.2(2) . . ? O8 C18 C17 118.7(2) . . ? O8 C18 C19 120.9(2) . . ? C17 C18 C19 120.4(2) . . ? O9 C19 C18 114.92(19) . . ? O9 C19 C20 124.5(2) . . ? C18 C19 C20 120.6(2) . . ? C21 C20 C19 117.3(2) . . ? C21 C20 C22 122.64(19) . . ? C19 C20 C22 120.01(19) . . ? C16 C21 C20 123.5(2) . . ? C20 C22 C22A 114.29(18) . . ? C20 C22 C23 110.14(17) . . ? C22A C22 C23 111.87(19) . . ? C22B C22A C22 112.8(2) . . ? C22C C22B C22A 113.0(2) . . ? C24 C23 C28 118.1(2) . . ? C24 C23 C22 120.9(2) . . ? C28 C23 C22 121.0(2) . . ? C23 C24 O10 121.5(2) . . ? C23 C24 C25 120.6(2) . . ? O10 C24 C25 117.8(2) . . ? O11 C25 C26 117.9(2) . . ? O11 C25 C24 122.3(2) . . ? C26 C25 C24 119.8(2) . . ? O12 C26 C25 117.0(2) . . ? O12 C26 C27 121.6(2) . . ? C25 C26 C27 121.4(2) . . ? C26 C27 C28 117.8(2) . . ? C26 C27 C1 121.26(19) . . ? C28 C27 C1 120.9(2) . . ? C23 C28 C27 122.2(2) . . ? N1 CN2 CN1 178.9(4) . . ? N3 CN5 CN6 179.7(4) . . ? N2 CN4 CN3 178(2) . . ? N4 CN7 CN8 175.3(10) . . ? O07 O07A O07A 148.8(7) . 2_696 ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.567 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.098