# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'David Bardelang' _publ_contact_author_name 'David Bardelang' _publ_contact_author_email DAVID.BARDELANG@UNIV-PROVENCE.FR _publ_section_title ; Inclusion complexes of coumarin in cucurbiturils ; # Attachment 'david11.cif' data_david11 _database_code_depnum_ccdc_archive 'CCDC 720730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common cucurbit[8]uril _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H60.80 N32 O20.40' _chemical_formula_weight 1628.67 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 tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 28.3633(9) _cell_length_b 28.3633(9) _cell_length_c 21.8616(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 17587.1(15) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6752 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 226081 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 23.31 _reflns_number_total 6281 _reflns_number_gt 5390 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ATOMS V.5.0' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1196P)^2^+8.4743P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00104(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6281 _refine_ls_number_parameters 554 _refine_ls_number_restraints 420 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.2368 _refine_ls_wR_factor_gt 0.2292 _refine_ls_goodness_of_fit_ref 1.507 _refine_ls_restrained_S_all 1.595 _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 O1 O 0.54895(9) 0.31140(8) 0.23215(12) 0.0552(7) Uani 1 1 d . . . O2 O 0.69991(7) 0.42446(8) 0.09606(9) 0.0374(5) Uani 1 1 d . . . O3 O 0.59780(8) 0.34887(8) 0.38006(10) 0.0453(6) Uani 1 1 d D . . O4 O 0.75127(7) 0.45414(7) 0.24454(8) 0.0310(5) Uani 1 1 d . . . O5 O 0.69123(7) 0.29419(7) 0.49066(9) 0.0360(5) Uani 1 1 d . . . O6 O 0.84768(7) 0.40165(8) 0.35563(9) 0.0380(5) Uani 1 1 d . . . O7 O 0.77500(7) 0.18471(7) 0.49832(9) 0.0349(5) Uani 1 1 d . . . O8 O 0.93360(7) 0.29401(8) 0.37120(11) 0.0430(6) Uani 1 1 d . . . N1 N 0.58280(9) 0.27226(9) 0.07224(12) 0.0375(7) Uani 1 1 d . . . N2 N 0.64473(9) 0.31608(8) 0.01958(11) 0.0317(6) Uani 1 1 d . . . N3 N 0.56891(9) 0.33990(9) 0.13722(12) 0.0363(6) Uani 1 1 d . . . N4 N 0.62994(9) 0.38353(8) 0.08454(10) 0.0301(6) Uani 1 1 d . . . N5 N 0.57717(8) 0.38701(9) 0.21743(11) 0.0339(6) Uani 1 1 d . . . N6 N 0.63754(8) 0.43149(8) 0.16379(10) 0.0292(6) Uani 1 1 d . . . N7 N 0.60987(9) 0.41083(9) 0.31468(11) 0.0364(6) Uani 1 1 d . . . N8 N 0.67118(8) 0.45456(8) 0.26087(10) 0.0284(6) Uani 1 1 d . . . N9 N 0.65668(8) 0.40335(9) 0.39520(11) 0.0304(6) Uani 1 1 d . . . N10 N 0.71873(8) 0.44482(8) 0.34070(10) 0.0283(6) Uani 1 1 d . . . N11 N 0.71483(8) 0.36884(8) 0.46191(11) 0.0293(6) Uani 1 1 d . . . N12 N 0.77731(8) 0.41043(8) 0.40705(10) 0.0287(6) Uani 1 1 d . . . N13 N 0.76840(8) 0.31851(8) 0.49784(11) 0.0314(6) Uani 1 1 d . . . N14 N 0.83054(8) 0.36067(8) 0.44403(11) 0.0313(6) Uani 1 1 d . . . N15 N 0.82076(8) 0.25158(8) 0.50388(11) 0.0318(6) Uani 1 1 d . . . N16 N 0.88444(8) 0.29519(8) 0.45458(11) 0.0315(6) Uani 1 1 d . . . C1 C 0.60564(10) 0.28351(10) 0.01458(14) 0.0341(7) Uani 1 1 d . . . H1 H 0.5824 0.2938 -0.0171 0.041 Uiso 1 1 calc R . . C2 C 0.54819(11) 0.30230(11) 0.10094(16) 0.0420(8) Uani 1 1 d . . . H2A H 0.5278 0.2828 0.1276 0.050 Uiso 1 1 calc R . . H2B H 0.5280 0.3164 0.0689 0.050 Uiso 1 1 calc R . . C3 C 0.58343(10) 0.38426(10) 0.11077(13) 0.0324(7) Uani 1 1 d . . . H3 H 0.5595 0.3965 0.0812 0.039 Uiso 1 1 calc R . . C4 C 0.63923(12) 0.36634(10) 0.02308(13) 0.0336(7) Uani 1 1 d . . . H4A H 0.6129 0.3759 -0.0039 0.040 Uiso 1 1 calc R . . H4B H 0.6683 0.3815 0.0075 0.040 Uiso 1 1 calc R . . C5 C 0.65985(10) 0.41413(10) 0.11332(13) 0.0295(7) Uani 1 1 d . . . C6 C 0.58876(10) 0.41719(10) 0.16684(13) 0.0303(7) Uani 1 1 d . . . H6 H 0.5670 0.4448 0.1643 0.036 Uiso 1 1 calc R . . C7 C 0.56335(11) 0.34305(11) 0.19848(15) 0.0375(8) Uani 1 1 d . . . C8 C 0.56772(10) 0.40503(13) 0.27840(13) 0.0375(8) Uani 1 1 d . . . H8A H 0.5516 0.4359 0.2749 0.045 Uiso 1 1 calc R . . H8B H 0.5461 0.3831 0.2997 0.045 Uiso 1 1 calc R . . C9 C 0.63870(10) 0.45304(10) 0.31202(12) 0.0288(7) Uani 1 1 d . . . H9 H 0.6193 0.4824 0.3149 0.035 Uiso 1 1 calc R . . C10 C 0.65742(11) 0.46949(10) 0.20029(12) 0.0292(7) Uani 1 1 d . . . H10A H 0.6853 0.4824 0.1789 0.035 Uiso 1 1 calc R . . H10B H 0.6339 0.4951 0.2039 0.035 Uiso 1 1 calc R . . C11 C 0.71706(10) 0.45142(9) 0.27812(12) 0.0265(7) Uani 1 1 d . . . C12 C 0.67189(10) 0.44721(10) 0.36797(12) 0.0277(7) Uani 1 1 d . . . H12 H 0.6690 0.4742 0.3972 0.033 Uiso 1 1 calc R . . C13 C 0.61934(10) 0.38406(11) 0.36441(13) 0.0330(7) Uani 1 1 d . . . C14 C 0.66873(11) 0.38980(11) 0.45714(13) 0.0341(7) Uani 1 1 d . . . H14A H 0.6674 0.4180 0.4837 0.041 Uiso 1 1 calc R . . H14B H 0.6450 0.3671 0.4723 0.041 Uiso 1 1 calc R . . C15 C 0.75750(10) 0.39701(10) 0.46549(12) 0.0284(7) Uani 1 1 d . . . H15 H 0.7533 0.4249 0.4930 0.034 Uiso 1 1 calc R . . C16 C 0.76119(10) 0.45232(10) 0.37477(13) 0.0302(7) Uani 1 1 d . . . H16A H 0.7558 0.4779 0.4048 0.036 Uiso 1 1 calc R . . H16B H 0.7863 0.4629 0.3464 0.036 Uiso 1 1 calc R . . C17 C 0.82098(10) 0.39193(10) 0.39782(13) 0.0307(7) Uani 1 1 d . . . C18 C 0.79449(10) 0.36246(10) 0.49078(12) 0.0284(7) Uani 1 1 d . . . H18 H 0.8076 0.3736 0.5307 0.034 Uiso 1 1 calc R . . C19 C 0.72170(10) 0.32444(10) 0.48417(12) 0.0296(7) Uani 1 1 d . . . C20 C 0.78548(11) 0.28041(10) 0.53468(14) 0.0335(7) Uani 1 1 d . . . H20A H 0.7586 0.2601 0.5465 0.040 Uiso 1 1 calc R . . H20B H 0.7993 0.2934 0.5726 0.040 Uiso 1 1 calc R . . C21 C 0.87036(11) 0.26364(10) 0.50293(14) 0.0324(7) Uani 1 1 d . . . H21 H 0.8813 0.2752 0.5438 0.039 Uiso 1 1 calc R . . C22 C 0.87774(10) 0.34584(10) 0.45797(15) 0.0346(8) Uani 1 1 d . . . H22A H 0.8859 0.3566 0.4997 0.041 Uiso 1 1 calc R . . H22B H 0.8997 0.3613 0.4291 0.041 Uiso 1 1 calc R . . C23 C 0.91336(10) 0.27458(11) 0.41360(14) 0.0330(7) Uani 1 1 d . . . C24 C 0.81318(11) 0.20494(10) 0.49398(12) 0.0298(7) Uani 1 1 d . . . O1A O 0.6683(3) 0.18534(18) 0.2584(2) 0.1033(15) Uani 0.551(3) 1 d PDU A 22 O2A O 0.5957(3) 0.2018(2) 0.2542(3) 0.1185(18) Uani 0.551(3) 1 d PDU A 22 C1A C 0.71859(17) 0.22949(15) 0.3254(2) 0.0830(16) Uani 0.551(3) 1 d PGDU A 22 C2A C 0.76303(19) 0.23644(18) 0.3506(2) 0.0946(18) Uani 0.551(3) 1 d PGDU A 22 H2A1 H 0.7677 0.2602 0.3807 0.114 Uiso 0.551(3) 1 calc PR A 22 C3A C 0.80071(17) 0.2086(2) 0.3319(3) 0.099(2) Uani 0.551(3) 1 d PGDU A 22 H3A H 0.8311 0.2134 0.3491 0.119 Uiso 0.551(3) 1 calc PR A 22 C4A C 0.7939(2) 0.17388(19) 0.2879(3) 0.094(2) Uani 0.551(3) 1 d PGDU A 22 H4A1 H 0.8197 0.1549 0.2751 0.113 Uiso 0.551(3) 1 calc PR A 22 C5A C 0.7495(2) 0.16693(16) 0.2627(2) 0.0899(17) Uani 0.551(3) 1 d PGDU A 22 H5A H 0.7449 0.1432 0.2327 0.108 Uiso 0.551(3) 1 calc PR A 22 C6A C 0.71182(19) 0.19473(16) 0.2815(2) 0.0867(18) Uani 0.551(3) 1 d PGDU A 22 C7A C 0.6334(3) 0.2188(3) 0.2660(3) 0.112(2) Uani 0.551(3) 1 d PDU A 22 C8A C 0.6354(3) 0.2483(3) 0.3166(4) 0.100(2) Uani 0.551(3) 1 d PDU A 22 H8A1 H 0.6076 0.2619 0.3333 0.121 Uiso 0.551(3) 1 calc PR A 22 C9A C 0.6786(3) 0.2573(3) 0.3417(3) 0.0832(17) Uani 0.551(3) 1 d PDU A 22 H9A H 0.6821 0.2823 0.3703 0.100 Uiso 0.551(3) 1 calc PR A 22 O1B O 0.6800(3) 0.22965(19) 0.3406(3) 0.1033(15) Uani 0.449(3) 1 d PDU A 23 O2B O 0.60632(7) 0.25106(18) 0.33856(19) 0.1185(18) Uani 0.449(3) 1 d PDU A 23 C1B C 0.7141(2) 0.19232(18) 0.2536(3) 0.0830(16) Uani 0.449(3) 1 d PGDU A 23 C2B C 0.7534(2) 0.1723(2) 0.2258(3) 0.0946(18) Uani 0.449(3) 1 d PGDU A 23 H2B1 H 0.7513 0.1607 0.1852 0.114 Uiso 0.449(3) 1 calc PR A 23 C3B C 0.7958(2) 0.1692(2) 0.2575(3) 0.099(2) Uani 0.449(3) 1 d PGDU A 23 H3B H 0.8226 0.1555 0.2386 0.119 Uiso 0.449(3) 1 calc PR A 23 C4B C 0.7989(2) 0.1862(3) 0.3171(3) 0.094(2) Uani 0.449(3) 1 d PGDU A 23 H4B1 H 0.8278 0.1841 0.3387 0.113 Uiso 0.449(3) 1 calc PR A 23 C5B C 0.7596(3) 0.2062(3) 0.3449(2) 0.0899(17) Uani 0.449(3) 1 d PGDU A 23 H5B H 0.7617 0.2178 0.3855 0.108 Uiso 0.449(3) 1 calc PR A 23 C6B C 0.7173(2) 0.2093(2) 0.3131(3) 0.0867(18) Uani 0.449(3) 1 d PGDU A 23 C7B C 0.64065(15) 0.2424(3) 0.3069(3) 0.112(2) Uani 0.449(3) 1 d PDU A 23 C8B C 0.6314(4) 0.2157(4) 0.2548(5) 0.100(2) Uani 0.449(3) 1 d PDU A 23 H8B1 H 0.6000 0.2103 0.2412 0.121 Uiso 0.449(3) 1 calc PR A 23 C9B C 0.6700(4) 0.1969(3) 0.2234(4) 0.0832(17) Uani 0.449(3) 1 d PDU A 23 H9B H 0.6668 0.1873 0.1820 0.100 Uiso 0.449(3) 1 calc PR A 23 O1W O 0.5768(4) 0.2807(4) 0.4562(5) 0.058(3) Uani 0.20 1 d PD . . H1W H 0.5519 0.3039 0.4629 0.069 Uiso 0.20 1 d PD . . H1Y H 0.5807 0.2745 0.4125 0.069 Uiso 0.20 1 d PD . . 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 0.0610(15) 0.0442(14) 0.0603(15) 0.0151(12) 0.0091(12) -0.0093(12) O2 0.0369(12) 0.0454(12) 0.0298(11) -0.0051(9) 0.0081(9) -0.0049(9) O3 0.0423(12) 0.0523(14) 0.0413(13) 0.0055(10) 0.0032(10) -0.0146(10) O4 0.0332(11) 0.0355(11) 0.0244(10) 0.0029(8) 0.0037(8) -0.0041(9) O5 0.0357(11) 0.0322(11) 0.0402(12) -0.0008(9) 0.0058(9) -0.0031(9) O6 0.0334(11) 0.0459(12) 0.0345(11) 0.0011(9) 0.0046(9) -0.0024(9) O7 0.0402(12) 0.0291(11) 0.0354(11) 0.0021(8) 0.0031(9) -0.0054(9) O8 0.0316(11) 0.0451(13) 0.0523(13) -0.0025(11) 0.0094(10) -0.0056(10) N1 0.0339(14) 0.0300(14) 0.0485(15) -0.0058(11) 0.0071(12) -0.0032(11) N2 0.0372(14) 0.0249(12) 0.0328(13) -0.0024(10) 0.0005(11) -0.0001(10) N3 0.0313(13) 0.0342(14) 0.0433(15) -0.0116(11) 0.0089(11) -0.0079(11) N4 0.0373(13) 0.0312(13) 0.0219(12) -0.0043(10) 0.0042(10) -0.0039(10) N5 0.0328(13) 0.0402(14) 0.0288(13) 0.0015(11) -0.0029(11) -0.0056(11) N6 0.0298(13) 0.0332(13) 0.0246(12) -0.0060(10) 0.0027(10) -0.0037(10) N7 0.0340(14) 0.0497(15) 0.0255(13) 0.0043(11) 0.0004(10) -0.0075(12) N8 0.0294(13) 0.0338(13) 0.0219(12) 0.0005(10) 0.0000(10) 0.0014(10) N9 0.0274(12) 0.0382(14) 0.0256(12) 0.0038(10) 0.0004(10) 0.0008(10) N10 0.0284(12) 0.0352(13) 0.0213(12) 0.0003(10) 0.0019(10) 0.0000(10) N11 0.0263(12) 0.0321(13) 0.0295(13) 0.0042(10) 0.0028(10) 0.0015(10) N12 0.0254(12) 0.0360(13) 0.0247(12) 0.0014(10) -0.0004(10) -0.0020(10) N13 0.0307(13) 0.0263(13) 0.0371(14) 0.0023(10) -0.0005(10) -0.0023(10) N14 0.0286(13) 0.0292(13) 0.0362(14) 0.0013(11) 0.0025(10) 0.0014(10) N15 0.0315(13) 0.0290(13) 0.0349(13) -0.0021(10) 0.0014(10) -0.0003(11) N16 0.0283(12) 0.0269(13) 0.0394(14) 0.0006(11) 0.0002(11) -0.0001(10) C1 0.0284(15) 0.0301(16) 0.0438(17) -0.0075(13) -0.0039(13) 0.0041(12) C2 0.0316(16) 0.0340(17) 0.060(2) -0.0139(15) 0.0085(15) -0.0043(13) C3 0.0352(16) 0.0310(16) 0.0310(16) -0.0022(13) -0.0023(13) 0.0045(13) C4 0.0505(18) 0.0275(15) 0.0229(14) 0.0006(12) 0.0028(13) 0.0026(13) C5 0.0353(16) 0.0268(15) 0.0264(15) 0.0000(12) 0.0016(13) 0.0058(12) C6 0.0254(15) 0.0337(16) 0.0318(15) -0.0022(13) -0.0021(12) 0.0028(12) C7 0.0345(16) 0.0340(17) 0.0441(19) -0.0004(15) 0.0025(14) 0.0040(13) C8 0.0273(15) 0.057(2) 0.0279(15) -0.0028(14) 0.0025(13) -0.0054(14) C9 0.0278(15) 0.0348(16) 0.0237(14) -0.0010(12) 0.0042(12) 0.0035(12) C10 0.0369(16) 0.0275(15) 0.0231(14) 0.0001(12) -0.0027(12) -0.0025(12) C11 0.0299(15) 0.0243(14) 0.0253(14) -0.0010(11) 0.0019(12) -0.0019(12) C12 0.0302(15) 0.0328(15) 0.0201(14) -0.0005(12) 0.0030(12) 0.0041(12) C13 0.0331(16) 0.0373(17) 0.0285(16) -0.0018(13) 0.0050(13) -0.0006(13) C14 0.0339(16) 0.0427(17) 0.0257(15) 0.0038(13) 0.0067(12) 0.0026(13) C15 0.0339(16) 0.0274(15) 0.0238(14) -0.0021(11) -0.0010(12) -0.0006(12) C16 0.0320(15) 0.0309(15) 0.0277(14) 0.0018(12) -0.0006(12) -0.0024(12) C17 0.0348(16) 0.0305(16) 0.0269(15) -0.0078(12) 0.0017(13) -0.0058(13) C18 0.0335(15) 0.0287(15) 0.0229(14) -0.0027(12) -0.0009(12) -0.0014(12) C19 0.0328(16) 0.0321(16) 0.0240(14) -0.0034(12) 0.0033(12) 0.0002(13) C20 0.0372(16) 0.0264(15) 0.0368(17) 0.0005(13) 0.0038(13) 0.0016(13) C21 0.0336(16) 0.0302(16) 0.0334(16) -0.0025(12) -0.0022(13) -0.0007(13) C22 0.0294(16) 0.0264(15) 0.0479(18) -0.0005(13) -0.0010(14) -0.0020(12) C23 0.0254(15) 0.0339(16) 0.0396(17) -0.0079(14) -0.0019(13) -0.0046(13) C24 0.0382(17) 0.0295(16) 0.0218(14) 0.0022(12) 0.0012(12) -0.0005(13) O1A 0.159(3) 0.064(3) 0.087(3) -0.003(2) -0.010(3) -0.011(3) O2A 0.156(4) 0.097(4) 0.102(4) 0.039(3) -0.018(3) -0.027(3) C1A 0.135(3) 0.047(3) 0.066(3) 0.022(3) -0.011(3) 0.000(3) C2A 0.168(4) 0.068(4) 0.048(3) 0.008(3) -0.035(3) 0.034(4) C3A 0.160(5) 0.070(4) 0.067(4) 0.014(3) -0.023(4) 0.035(4) C4A 0.171(4) 0.063(4) 0.050(5) 0.024(3) -0.025(4) 0.030(4) C5A 0.165(4) 0.038(3) 0.067(4) 0.012(3) -0.005(3) 0.003(4) C6A 0.144(4) 0.053(4) 0.063(4) 0.010(3) -0.002(3) -0.007(3) C7A 0.144(4) 0.101(5) 0.091(5) -0.041(4) -0.032(4) -0.007(4) C8A 0.110(4) 0.109(5) 0.082(4) -0.005(3) 0.021(3) -0.046(4) C9A 0.133(4) 0.063(4) 0.054(3) -0.006(3) -0.012(3) -0.013(3) O1B 0.159(3) 0.064(3) 0.087(3) -0.003(2) -0.010(3) -0.011(3) O2B 0.156(4) 0.097(4) 0.102(4) 0.039(3) -0.018(3) -0.027(3) C1B 0.135(3) 0.047(3) 0.066(3) 0.022(3) -0.011(3) 0.000(3) C2B 0.168(4) 0.068(4) 0.048(3) 0.008(3) -0.035(3) 0.034(4) C3B 0.160(5) 0.070(4) 0.067(4) 0.014(3) -0.023(4) 0.035(4) C4B 0.171(4) 0.063(4) 0.050(5) 0.024(3) -0.025(4) 0.030(4) C5B 0.165(4) 0.038(3) 0.067(4) 0.012(3) -0.005(3) 0.003(4) C6B 0.144(4) 0.053(4) 0.063(4) 0.010(3) -0.002(3) -0.007(3) C7B 0.144(4) 0.101(5) 0.091(5) -0.041(4) -0.032(4) -0.007(4) C8B 0.110(4) 0.109(5) 0.082(4) -0.005(3) 0.021(3) -0.046(4) C9B 0.133(4) 0.063(4) 0.054(3) -0.006(3) -0.012(3) -0.013(3) O1W 0.080(8) 0.045(7) 0.049(7) 0.021(5) -0.022(6) -0.029(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.231(4) . ? O2 C5 1.233(4) . ? O3 C13 1.219(4) . ? O4 C11 1.219(3) . ? O5 C19 1.226(4) . ? O6 C17 1.225(4) . ? O7 C24 1.229(4) . ? O8 C23 1.222(4) . ? N1 C23 1.368(4) 13_655 ? N1 C2 1.443(4) . ? N1 C1 1.453(4) . ? N2 C24 1.367(4) 13_655 ? N2 C4 1.436(4) . ? N2 C1 1.448(4) . ? N3 C7 1.351(4) . ? N3 C3 1.445(4) . ? N3 C2 1.453(4) . ? N4 C5 1.367(4) . ? N4 C3 1.439(4) . ? N4 C4 1.453(4) . ? N5 C7 1.371(4) . ? N5 C6 1.437(4) . ? N5 C8 1.453(4) . ? N6 C5 1.364(4) . ? N6 C6 1.443(4) . ? N6 C10 1.455(4) . ? N7 C13 1.353(4) . ? N7 C8 1.444(4) . ? N7 C9 1.451(4) . ? N8 C11 1.358(4) . ? N8 C10 1.444(4) . ? N8 C9 1.450(4) . ? N9 C13 1.369(4) . ? N9 C12 1.445(4) . ? N9 C14 1.448(4) . ? N10 C11 1.382(4) . ? N10 C16 1.432(4) . ? N10 C12 1.458(4) . ? N11 C19 1.364(4) . ? N11 C14 1.440(4) . ? N11 C15 1.453(4) . ? N12 C17 1.360(4) . ? N12 C15 1.447(4) . ? N12 C16 1.456(4) . ? N13 C19 1.368(4) . ? N13 C20 1.432(4) . ? N13 C18 1.458(4) . ? N14 C17 1.371(4) . ? N14 C22 1.436(4) . ? N14 C18 1.447(4) . ? N15 C24 1.358(4) . ? N15 C21 1.448(4) . ? N15 C20 1.457(4) . ? N16 C23 1.348(4) . ? N16 C21 1.441(4) . ? N16 C22 1.451(4) . ? C1 C21 1.549(4) 13_655 ? C3 C6 1.548(4) . ? C9 C12 1.552(4) . ? C15 C18 1.539(4) . ? C21 C1 1.549(4) 13_655 ? C23 N1 1.368(4) 13_655 ? C24 N2 1.367(4) 13_655 ? O1A C6A 1.361(8) . ? O1A C7A 1.381(10) . ? O2A C7A 1.200(10) . ? C1A C2A 1.3900 . ? C1A C6A 1.3900 . ? C1A C9A 1.426(9) . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C5A C6A 1.3900 . ? C7A C8A 1.388(11) . ? C8A C9A 1.368(11) . ? O1B C6B 1.346(9) . ? O1B C7B 1.385(9) . ? O2B C7B 1.2199(11) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C9B 1.422(10) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.393(11) . ? C8B C9B 1.398(13) . ? 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 C23 N1 C2 121.9(3) 13_655 . ? C23 N1 C1 112.0(2) 13_655 . ? C2 N1 C1 123.4(3) . . ? C24 N2 C4 122.7(2) 13_655 . ? C24 N2 C1 112.0(2) 13_655 . ? C4 N2 C1 123.7(2) . . ? C7 N3 C3 111.9(2) . . ? C7 N3 C2 122.8(3) . . ? C3 N3 C2 122.4(3) . . ? C5 N4 C3 112.1(2) . . ? C5 N4 C4 121.7(2) . . ? C3 N4 C4 122.7(2) . . ? C7 N5 C6 112.0(2) . . ? C7 N5 C8 123.0(3) . . ? C6 N5 C8 122.6(3) . . ? C5 N6 C6 112.4(2) . . ? C5 N6 C10 122.1(2) . . ? C6 N6 C10 123.7(2) . . ? C13 N7 C8 122.8(3) . . ? C13 N7 C9 112.5(2) . . ? C8 N7 C9 122.6(2) . . ? C11 N8 C10 122.2(2) . . ? C11 N8 C9 113.1(2) . . ? C10 N8 C9 123.0(2) . . ? C13 N9 C12 111.9(2) . . ? C13 N9 C14 122.4(2) . . ? C12 N9 C14 122.9(2) . . ? C11 N10 C16 121.6(2) . . ? C11 N10 C12 111.6(2) . . ? C16 N10 C12 123.2(2) . . ? C19 N11 C14 122.5(2) . . ? C19 N11 C15 111.7(2) . . ? C14 N11 C15 122.2(2) . . ? C17 N12 C15 112.5(2) . . ? C17 N12 C16 121.9(2) . . ? C15 N12 C16 121.4(2) . . ? C19 N13 C20 122.9(2) . . ? C19 N13 C18 111.3(2) . . ? C20 N13 C18 122.2(2) . . ? C17 N14 C22 122.0(2) . . ? C17 N14 C18 111.0(2) . . ? C22 N14 C18 121.3(2) . . ? C24 N15 C21 112.5(2) . . ? C24 N15 C20 120.8(2) . . ? C21 N15 C20 122.8(2) . . ? C23 N16 C21 112.8(2) . . ? C23 N16 C22 122.9(2) . . ? C21 N16 C22 122.7(2) . . ? N2 C1 N1 114.6(2) . . ? N2 C1 C21 103.5(2) . 13_655 ? N1 C1 C21 102.8(2) . 13_655 ? N1 C2 N3 113.3(3) . . ? N4 C3 N3 114.1(2) . . ? N4 C3 C6 103.6(2) . . ? N3 C3 C6 103.7(2) . . ? N2 C4 N4 113.7(2) . . ? O2 C5 N6 126.1(3) . . ? O2 C5 N4 125.6(3) . . ? N6 C5 N4 108.3(2) . . ? N5 C6 N6 115.0(2) . . ? N5 C6 C3 103.2(2) . . ? N6 C6 C3 103.1(2) . . ? O1 C7 N3 125.7(3) . . ? O1 C7 N5 125.3(3) . . ? N3 C7 N5 109.0(3) . . ? N7 C8 N5 113.0(2) . . ? N8 C9 N7 114.4(2) . . ? N8 C9 C12 103.0(2) . . ? N7 C9 C12 102.8(2) . . ? N8 C10 N6 113.0(2) . . ? O4 C11 N8 126.3(3) . . ? O4 C11 N10 125.3(3) . . ? N8 C11 N10 108.5(2) . . ? N9 C12 N10 113.6(2) . . ? N9 C12 C9 103.6(2) . . ? N10 C12 C9 103.6(2) . . ? O3 C13 N7 125.8(3) . . ? O3 C13 N9 125.2(3) . . ? N7 C13 N9 108.9(3) . . ? N11 C14 N9 113.1(2) . . ? N12 C15 N11 114.9(2) . . ? N12 C15 C18 102.7(2) . . ? N11 C15 C18 103.7(2) . . ? N10 C16 N12 113.3(2) . . ? O6 C17 N12 126.0(3) . . ? O6 C17 N14 125.3(3) . . ? N12 C17 N14 108.7(2) . . ? N14 C18 N13 113.8(2) . . ? N14 C18 C15 104.5(2) . . ? N13 C18 C15 103.7(2) . . ? O5 C19 N11 125.9(3) . . ? O5 C19 N13 124.8(3) . . ? N11 C19 N13 109.3(2) . . ? N13 C20 N15 113.3(2) . . ? N16 C21 N15 115.2(2) . . ? N16 C21 C1 103.5(2) . 13_655 ? N15 C21 C1 103.1(2) . 13_655 ? N14 C22 N16 113.7(2) . . ? O8 C23 N16 126.5(3) . . ? O8 C23 N1 124.9(3) . 13_655 ? N16 C23 N1 108.6(3) . 13_655 ? O7 C24 N15 125.6(3) . . ? O7 C24 N2 125.6(3) . 13_655 ? N15 C24 N2 108.7(3) . 13_655 ? C6A O1A C7A 118.1(6) . . ? C2A C1A C6A 120.0 . . ? C2A C1A C9A 122.9(4) . . ? C6A C1A C9A 117.1(4) . . ? C3A C2A C1A 120.0 . . ? C4A C3A C2A 120.0 . . ? C3A C4A C5A 120.0 . . ? C6A C5A C4A 120.0 . . ? O1A C6A C5A 118.6(4) . . ? O1A C6A C1A 121.3(4) . . ? C5A C6A C1A 120.0 . . ? O2A C7A O1A 109.7(8) . . ? O2A C7A C8A 116.8(8) . . ? O1A C7A C8A 118.7(7) . . ? C9A C8A C7A 118.0(8) . . ? C8A C9A C1A 120.6(7) . . ? C6B O1B C7B 120.5(6) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C9B 122.7(5) . . ? C6B C1B C9B 117.3(5) . . ? C1B C2B C3B 120.0 . . ? C4B C3B C2B 120.0 . . ? C3B C4B C5B 120.0 . . ? C4B C5B C6B 120.0 . . ? O1B C6B C5B 118.9(5) . . ? O1B C6B C1B 121.1(5) . . ? C5B C6B C1B 120.0 . . ? O2B C7B O1B 113.1(6) . . ? O2B C7B C8B 115.0(6) . . ? O1B C7B C8B 116.3(7) . . ? C7B C8B C9B 117.5(8) . . ? C8B C9B C1B 119.7(8) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.672 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.082