# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Oren Scherman' _publ_contact_author_email OAS23@CAM.AC.UK _publ_section_title ; Controlled catch and release of small molecules with cucurbit[6]uril via a kinetic trap ; loop_ _publ_author_name 'Oren Scherman' 'Li Liu.' 'Nicolas Nouvel' data_sc0701 _database_code_depnum_ccdc_archive 'CCDC 720410' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H36 N24 O12, C4 H10 O, 8(H2 O)' _chemical_formula_sum 'C40 H62 N24 O21' _chemical_formula_weight 1215.14 _chemical_absolute_configuration ; 2134 Friedel pairs were averaged for the refinement. ; 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 Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 19.5755(7) _cell_length_b 15.9105(10) _cell_length_c 16.0489(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4998.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 17993 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2552 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 1.012 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor (small, weakly diffracting) crystal: theta(max)=25degrees. The ether molecule is poorly resolved, modelled as disordered over two sites. The water hydrogen atoms were placed in resonable positions: some were visible in the final difference maps. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 16080 _diffrn_reflns_av_R_equivalents 0.1245 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.15 _reflns_number_total 2372 _reflns_number_gt 1794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0777P)^2^+12.9695P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2372 _refine_ls_number_parameters 415 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1684 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 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 0.5000 0.3275(5) -0.2853(5) 0.0389(18) Uani 1 2 d S . . O2 O 0.5000 0.6069(5) -0.0139(4) 0.0384(17) Uani 1 2 d S . . O3 O 0.6690(3) 0.5241(3) 0.0614(3) 0.0394(13) Uani 1 1 d . . . O4 O 0.6647(3) 0.2529(3) -0.2190(3) 0.0428(14) Uani 1 1 d . . . O5 O 0.6639(3) 0.0942(4) -0.0704(3) 0.0462(15) Uani 1 1 d . . . O6 O 0.6640(3) 0.3631(3) 0.2075(3) 0.0382(13) Uani 1 1 d . . . O7 O 0.5000 0.2873(5) 0.2771(5) 0.0387(18) Uani 1 2 d S . . O8 O 0.5000 0.0148(5) 0.0012(5) 0.0398(17) Uani 1 2 d S . . N1 N 0.5566(3) 0.4448(4) -0.2374(4) 0.0329(15) Uani 1 1 d . . . N2 N 0.5567(3) 0.5522(4) -0.1283(4) 0.0313(14) Uani 1 1 d . . . N3 N 0.6664(3) 0.5008(4) -0.0805(3) 0.0304(13) Uani 1 1 d . . . N4 N 0.6684(3) 0.3957(4) -0.1939(4) 0.0320(14) Uani 1 1 d . . . N5 N 0.7266(3) 0.3109(3) -0.1110(4) 0.0295(14) Uani 1 1 d . . . N6 N 0.7298(3) 0.4179(3) -0.0014(4) 0.0299(13) Uani 1 1 d . . . N7 N 0.7276(4) 0.3058(4) 0.1000(4) 0.0365(16) Uani 1 1 d . . . N8 N 0.7299(3) 0.1981(4) -0.0081(5) 0.0336(13) Uani 1 1 d . . . N9 N 0.6653(3) 0.1166(4) 0.0721(3) 0.0304(14) Uani 1 1 d . . . N10 N 0.6694(3) 0.2207(4) 0.1840(3) 0.0326(14) Uani 1 1 d . . . N11 N 0.5570(3) 0.1706(4) 0.2248(3) 0.0299(14) Uani 1 1 d . . . N12 N 0.5564(3) 0.0616(4) 0.1190(4) 0.0361(15) Uani 1 1 d . . . C1 C 0.5000 0.3980(7) -0.2564(6) 0.029(2) Uani 1 2 d S . . C2 C 0.5398(4) 0.5305(4) -0.2133(4) 0.0284(15) Uani 1 1 d . . . H2 H 0.5586 0.5724 -0.2537 0.034 Uiso 1 1 calc R . . C3 C 0.5000 0.5739(6) -0.0818(7) 0.033(2) Uani 1 2 d S . . C4 C 0.6251(4) 0.5730(5) -0.1024(5) 0.0337(17) Uani 1 1 d . . . H4A H 0.6226 0.6110 -0.0537 0.040 Uiso 1 1 calc RD . . H4B H 0.6480 0.6040 -0.1481 0.040 Uiso 1 1 calc R . . C5 C 0.6251(4) 0.4214(5) -0.2625(4) 0.0343(18) Uani 1 1 d . . . H5A H 0.6222 0.3747 -0.3031 0.041 Uiso 1 1 calc R . . H5B H 0.6466 0.4698 -0.2911 0.041 Uiso 1 1 calc R . . C6 C 0.6844(4) 0.3147(5) -0.1773(4) 0.0332(18) Uani 1 1 d . . . C7 C 0.7048(4) 0.4526(4) -0.1414(4) 0.0319(16) Uani 1 1 d . . . H7 H 0.7348 0.4903 -0.1753 0.038 Uiso 1 1 calc R . . C8 C 0.6860(3) 0.4838(4) -0.0004(5) 0.0284(15) Uani 1 1 d . . . C9 C 0.7489(4) 0.3933(5) -0.0855(4) 0.0320(17) Uani 1 1 d . . . H9 H 0.7988 0.4015 -0.0956 0.038 Uiso 1 1 calc R . . C10 C 0.7595(4) 0.2335(5) -0.0837(4) 0.0344(18) Uani 1 1 d . . . H10A H 0.7562 0.1913 -0.1289 0.041 Uiso 1 1 calc R . . H10B H 0.8086 0.2448 -0.0738 0.041 Uiso 1 1 calc R . . C11 C 0.7592(4) 0.3829(4) 0.0730(4) 0.0309(16) Uani 1 1 d . . . H11A H 0.7556 0.4248 0.1184 0.037 Uiso 1 1 calc R . . H11B H 0.8084 0.3723 0.0630 0.037 Uiso 1 1 calc R . . C12 C 0.6849(4) 0.3034(4) 0.1687(4) 0.0278(16) Uani 1 1 d . . . C13 C 0.7499(4) 0.2220(4) 0.0745(4) 0.0312(16) Uani 1 1 d . . . H13 H 0.8000 0.2141 0.0835 0.037 Uiso 1 1 calc RD . . C14 C 0.6837(4) 0.1327(4) -0.0090(5) 0.0362(17) Uani 1 1 d . . . C15 C 0.7072(4) 0.1624(5) 0.1308(4) 0.0316(16) Uani 1 1 d . . . H15 H 0.7370 0.1240 0.1641 0.038 Uiso 1 1 calc R . . C16 C 0.6254(4) 0.1951(5) 0.2519(4) 0.0321(16) Uani 1 1 d . . . H16A H 0.6214 0.2422 0.2920 0.039 Uiso 1 1 calc R . . H16B H 0.6468 0.1472 0.2814 0.039 Uiso 1 1 calc R . . C17 C 0.5400(4) 0.0854(4) 0.2033(5) 0.0304(16) Uani 1 1 d . . . H17 H 0.5589 0.0445 0.2446 0.037 Uiso 1 1 calc R . . C18 C 0.6258(4) 0.0429(4) 0.0929(4) 0.0310(17) Uani 1 1 d . . . H18A H 0.6493 0.0122 0.1383 0.037 Uiso 1 1 calc R . . H18B H 0.6242 0.0054 0.0437 0.037 Uiso 1 1 calc R . . C19 C 0.5000 0.0446(6) 0.0739(7) 0.033(2) Uani 1 2 d S . . C20 C 0.5000 0.2185(7) 0.2459(6) 0.032(2) Uani 1 2 d S . . C1E C 0.500(7) 0.195(2) -0.1041(19) 0.188(7) Uiso 1 2 d SD A -1 H1EA H 0.5054 0.2003 -0.1646 0.282 Uiso 0.50 1 calc PR A -1 H1EB H 0.4710 0.1467 -0.0914 0.282 Uiso 0.50 1 calc PR A -1 H1EC H 0.5452 0.1868 -0.0785 0.282 Uiso 0.50 1 calc PR A -1 C2E C 0.472(2) 0.265(2) -0.073(2) 0.188(7) Uiso 0.50 1 d PD A -1 H2EA H 0.4965 0.3142 -0.0966 0.226 Uiso 0.50 1 calc PR A -1 H2EB H 0.4240 0.2685 -0.0944 0.226 Uiso 0.50 1 calc PR A -1 O3E O 0.4698(13) 0.2734(15) 0.0083(16) 0.188(7) Uiso 0.50 1 d PD A -1 C4E C 0.458(2) 0.354(2) 0.032(3) 0.188(7) Uiso 0.50 1 d PD A -1 H4EA H 0.4404 0.3860 -0.0161 0.226 Uiso 0.50 1 calc PR A -1 H4EB H 0.4231 0.3546 0.0762 0.226 Uiso 0.50 1 calc PR A -1 C5E C 0.514(3) 0.394(2) 0.061(2) 0.188(7) Uiso 0.50 1 d PD A -1 H5EA H 0.5520 0.3534 0.0657 0.282 Uiso 0.50 1 calc PR A -1 H5EB H 0.5045 0.4178 0.1158 0.282 Uiso 0.50 1 calc PR A -1 H5EC H 0.5272 0.4386 0.0223 0.282 Uiso 0.50 1 calc PR A -1 O1W O 0.3419(4) 0.0641(6) -0.2390(4) 0.086(3) Uani 1 1 d D . . H11W H 0.348(9) 0.079(10) -0.179(3) 0.188(7) Uiso 1 1 d D . . H12W H 0.314(9) 0.108(8) -0.267(8) 0.188(7) Uiso 1 1 d D . . O2W O 0.5837(4) 0.7513(6) 0.0152(8) 0.121(4) Uani 1 1 d D . . H21W H 0.564(9) 0.767(10) 0.071(4) 0.188(7) Uiso 1 1 d D . . H22W H 0.615(6) 0.702(6) 0.022(6) 0.188(7) Uiso 1 1 d D . . O3W O 0.4293(8) 0.1700(5) -0.3332(6) 0.126(4) Uani 1 1 d D . . H31W H 0.414(10) 0.147(11) -0.388(5) 0.188(7) Uiso 1 1 d D . . H32W H 0.414(9) 0.131(9) -0.288(7) 0.188(7) Uiso 1 1 d D . . O4W O 0.5852(4) -0.1018(8) -0.0873(7) 0.142(5) Uani 1 1 d D . . H41W H 0.553(6) -0.145(8) -0.110(12) 0.188(7) Uiso 1 1 d D . . H42W H 0.558(6) -0.057(8) -0.058(11) 0.188(7) Uiso 1 1 d 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 O1 0.046(5) 0.040(5) 0.031(4) -0.007(3) 0.000 0.000 O2 0.040(4) 0.046(4) 0.029(4) -0.016(4) 0.000 0.000 O3 0.045(3) 0.045(3) 0.028(3) -0.006(2) 0.003(2) 0.007(3) O4 0.047(3) 0.041(3) 0.040(3) -0.005(3) -0.005(3) 0.002(3) O5 0.060(4) 0.050(3) 0.029(3) -0.007(2) 0.000(2) -0.010(3) O6 0.044(3) 0.032(3) 0.038(3) -0.005(2) 0.010(3) -0.002(3) O7 0.038(4) 0.034(4) 0.044(4) -0.009(4) 0.000 0.000 O8 0.037(4) 0.043(4) 0.039(4) -0.011(4) 0.000 0.000 N1 0.036(4) 0.031(3) 0.031(3) -0.001(3) 0.000(3) 0.007(3) N2 0.033(4) 0.036(4) 0.024(3) -0.001(3) -0.004(3) 0.003(3) N3 0.032(3) 0.034(3) 0.025(3) -0.003(2) 0.000(2) -0.003(3) N4 0.042(4) 0.027(3) 0.027(3) 0.004(2) -0.001(3) 0.001(3) N5 0.032(4) 0.028(3) 0.029(3) -0.001(2) -0.004(3) 0.002(2) N6 0.035(3) 0.034(3) 0.021(3) -0.001(3) 0.002(3) 0.004(3) N7 0.038(4) 0.039(4) 0.033(4) -0.005(3) 0.003(3) 0.001(3) N8 0.035(3) 0.034(3) 0.032(3) -0.004(3) -0.003(4) 0.004(3) N9 0.033(3) 0.034(3) 0.024(3) -0.006(3) 0.004(3) -0.001(3) N10 0.031(3) 0.042(4) 0.024(3) -0.002(3) 0.002(2) -0.002(3) N11 0.024(3) 0.034(4) 0.031(3) -0.003(3) -0.004(2) 0.003(3) N12 0.032(4) 0.044(4) 0.032(4) -0.006(3) 0.000(3) 0.003(3) C1 0.035(6) 0.035(6) 0.018(5) -0.003(4) 0.000 0.000 C2 0.030(4) 0.028(4) 0.027(4) 0.002(3) 0.001(3) -0.006(3) C3 0.040(6) 0.023(6) 0.035(6) 0.007(5) 0.000 0.000 C4 0.036(4) 0.029(4) 0.037(4) -0.003(3) 0.002(3) 0.001(3) C5 0.034(4) 0.047(5) 0.022(4) -0.003(3) 0.000(3) 0.007(4) C6 0.035(5) 0.040(5) 0.024(4) -0.001(3) 0.006(3) -0.002(4) C7 0.034(4) 0.030(4) 0.031(4) -0.002(3) 0.006(3) -0.006(3) C8 0.024(3) 0.035(4) 0.026(3) 0.000(3) 0.006(3) -0.011(3) C9 0.031(4) 0.038(4) 0.027(4) 0.003(3) 0.003(3) 0.000(3) C10 0.033(4) 0.038(5) 0.032(4) -0.003(3) 0.006(3) 0.000(4) C11 0.031(4) 0.031(4) 0.030(4) 0.001(3) 0.004(3) -0.006(3) C12 0.024(4) 0.034(4) 0.025(4) -0.002(3) 0.001(3) -0.002(3) C13 0.025(4) 0.037(4) 0.031(4) -0.005(3) -0.002(3) 0.006(3) C14 0.036(4) 0.031(4) 0.041(5) -0.005(4) -0.002(4) 0.008(3) C15 0.022(3) 0.044(5) 0.029(4) 0.005(3) -0.003(3) 0.003(3) C16 0.031(4) 0.042(4) 0.022(3) -0.001(3) 0.001(3) 0.000(3) C17 0.034(4) 0.025(4) 0.032(4) 0.003(3) 0.000(3) -0.001(3) C18 0.031(4) 0.029(4) 0.033(4) -0.008(3) 0.003(3) 0.007(3) C19 0.036(6) 0.034(6) 0.028(6) -0.010(5) 0.000 0.000 C20 0.037(6) 0.034(6) 0.025(5) -0.006(4) 0.000 0.000 O1W 0.091(6) 0.127(7) 0.040(4) -0.029(4) -0.004(4) 0.036(5) O2W 0.045(4) 0.114(7) 0.203(10) -0.093(7) 0.005(6) -0.001(4) O3W 0.230(12) 0.067(5) 0.081(6) -0.014(5) 0.047(7) -0.011(6) O4W 0.063(5) 0.208(12) 0.154(9) -0.128(9) 0.026(6) 0.000(7) _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 C1 1.214(12) . ? O2 C3 1.210(12) . ? O3 C8 1.226(9) . ? O4 C6 1.250(9) . ? O5 C14 1.222(9) . ? O6 C12 1.208(9) . ? O7 C20 1.204(12) . ? O8 C19 1.259(13) . ? N1 C1 1.369(9) . ? N1 C5 1.449(10) . ? N1 C2 1.455(9) . ? N2 C3 1.382(9) . ? N2 C4 1.441(9) . ? N2 C2 1.445(9) . ? N3 C8 1.370(9) . ? N3 C4 1.448(10) . ? N3 C7 1.452(9) . ? N4 C6 1.353(9) . ? N4 C7 1.428(9) . ? N4 C5 1.449(9) . ? N5 C6 1.348(10) . ? N5 C9 1.441(9) . ? N5 C10 1.458(10) . ? N6 C8 1.353(9) . ? N6 C11 1.438(9) . ? N6 C9 1.454(9) . ? N7 C12 1.384(10) . ? N7 C11 1.440(9) . ? N7 C13 1.462(9) . ? N8 C14 1.380(9) . ? N8 C13 1.433(10) . ? N8 C10 1.458(10) . ? N9 C14 1.376(10) . ? N9 C18 1.444(9) . ? N9 C15 1.446(9) . ? N10 C12 1.373(9) . ? N10 C16 1.448(9) . ? N10 C15 1.462(9) . ? N11 C20 1.394(8) . ? N11 C17 1.437(9) . ? N11 C16 1.460(9) . ? N12 C19 1.348(8) . ? N12 C17 1.441(10) . ? N12 C18 1.452(9) . ? C1 N1 1.369(9) 4_655 ? C2 C2 1.558(14) 4_655 ? C2 H2 1.0000 . ? C3 N2 1.382(9) 4_655 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 C9 1.561(10) . ? C7 H7 1.0000 . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 C15 1.553(10) . ? C13 H13 1.0000 . ? C15 H15 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C17 1.567(14) 4_655 ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N12 1.348(8) 4_655 ? C20 N11 1.394(8) 4_655 ? C1E C2E 1.35(3) . ? C1E H1EA 0.9800 . ? C1E H1EB 0.9800 . ? C1E H1EC 0.9800 . ? C2E O3E 1.32(3) . ? C2E H2EA 0.9900 . ? C2E H2EB 0.9900 . ? O3E C4E 1.36(2) . ? C4E C5E 1.34(3) . ? C4E H4EA 0.9900 . ? C4E H4EB 0.9900 . ? C5E H5EA 0.9800 . ? C5E H5EB 0.9800 . ? C5E H5EC 0.9800 . ? O1W H11W 1.00(2) . ? O1W H12W 1.00(2) . ? O2W H21W 1.00(2) . ? O2W H22W 1.00(2) . ? O3W H31W 1.00(2) . ? O3W H32W 1.01(2) . ? O4W H41W 1.00(2) . ? O4W H42W 1.00(2) . ? 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 C1 N1 C5 123.2(6) . . ? C1 N1 C2 112.7(6) . . ? C5 N1 C2 121.6(6) . . ? C3 N2 C4 122.2(6) . . ? C3 N2 C2 112.7(6) . . ? C4 N2 C2 122.7(6) . . ? C8 N3 C4 122.7(6) . . ? C8 N3 C7 112.5(6) . . ? C4 N3 C7 123.1(6) . . ? C6 N4 C7 111.9(6) . . ? C6 N4 C5 123.6(6) . . ? C7 N4 C5 124.2(6) . . ? C6 N5 C9 111.7(6) . . ? C6 N5 C10 123.0(6) . . ? C9 N5 C10 123.3(6) . . ? C8 N6 C11 123.0(6) . . ? C8 N6 C9 112.5(6) . . ? C11 N6 C9 124.2(5) . . ? C12 N7 C11 121.5(6) . . ? C12 N7 C13 112.2(6) . . ? C11 N7 C13 124.4(6) . . ? C14 N8 C13 112.9(7) . . ? C14 N8 C10 122.9(7) . . ? C13 N8 C10 124.0(6) . . ? C14 N9 C18 120.7(6) . . ? C14 N9 C15 112.0(6) . . ? C18 N9 C15 124.2(6) . . ? C12 N10 C16 122.4(6) . . ? C12 N10 C15 113.0(6) . . ? C16 N10 C15 124.3(6) . . ? C20 N11 C17 112.9(6) . . ? C20 N11 C16 121.0(6) . . ? C17 N11 C16 122.4(6) . . ? C19 N12 C17 112.0(6) . . ? C19 N12 C18 124.8(6) . . ? C17 N12 C18 122.2(6) . . ? O1 C1 N1 126.0(4) . 4_655 ? O1 C1 N1 126.0(4) . . ? N1 C1 N1 108.1(9) 4_655 . ? N2 C2 N1 115.1(6) . . ? N2 C2 C2 103.2(4) . 4_655 ? N1 C2 C2 103.1(4) . 4_655 ? N2 C2 H2 111.6 . . ? N1 C2 H2 111.6 . . ? C2 C2 H2 111.6 4_655 . ? O2 C3 N2 126.5(4) . 4_655 ? O2 C3 N2 126.5(4) . . ? N2 C3 N2 106.9(9) 4_655 . ? N2 C4 N3 114.0(6) . . ? N2 C4 H4A 108.8 . . ? N3 C4 H4A 108.8 . . ? N2 C4 H4B 108.8 . . ? N3 C4 H4B 108.8 . . ? H4A C4 H4B 107.6 . . ? N4 C5 N1 113.8(6) . . ? N4 C5 H5A 108.8 . . ? N1 C5 H5A 108.8 . . ? N4 C5 H5B 108.8 . . ? N1 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? O4 C6 N5 125.2(7) . . ? O4 C6 N4 124.9(7) . . ? N5 C6 N4 109.8(6) . . ? N4 C7 N3 118.3(6) . . ? N4 C7 C9 103.4(6) . . ? N3 C7 C9 102.6(5) . . ? N4 C7 H7 110.6 . . ? N3 C7 H7 110.6 . . ? C9 C7 H7 110.6 . . ? O3 C8 N6 125.9(7) . . ? O3 C8 N3 125.5(6) . . ? N6 C8 N3 108.6(6) . . ? N5 C9 N6 115.5(6) . . ? N5 C9 C7 102.6(6) . . ? N6 C9 C7 103.2(6) . . ? N5 C9 H9 111.6 . . ? N6 C9 H9 111.6 . . ? C7 C9 H9 111.6 . . ? N8 C10 N5 113.6(6) . . ? N8 C10 H10A 108.8 . . ? N5 C10 H10A 108.8 . . ? N8 C10 H10B 108.8 . . ? N5 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? N6 C11 N7 114.0(6) . . ? N6 C11 H11A 108.7 . . ? N7 C11 H11A 108.7 . . ? N6 C11 H11B 108.7 . . ? N7 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O6 C12 N10 125.9(7) . . ? O6 C12 N7 126.4(6) . . ? N10 C12 N7 107.7(6) . . ? N8 C13 N7 114.7(6) . . ? N8 C13 C15 103.3(6) . . ? N7 C13 C15 103.5(6) . . ? N8 C13 H13 111.6 . . ? N7 C13 H13 111.6 . . ? C15 C13 H13 111.6 . . ? O5 C14 N9 125.9(7) . . ? O5 C14 N8 126.5(8) . . ? N9 C14 N8 107.6(7) . . ? N9 C15 N10 114.3(6) . . ? N9 C15 C13 103.5(6) . . ? N10 C15 C13 103.0(6) . . ? N9 C15 H15 111.8 . . ? N10 C15 H15 111.8 . . ? C13 C15 H15 111.8 . . ? N10 C16 N11 113.3(5) . . ? N10 C16 H16A 108.9 . . ? N11 C16 H16A 108.9 . . ? N10 C16 H16B 108.9 . . ? N11 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? N11 C17 N12 115.0(6) . . ? N11 C17 C17 103.4(4) . 4_655 ? N12 C17 C17 102.8(4) . 4_655 ? N11 C17 H17 111.7 . . ? N12 C17 H17 111.7 . . ? C17 C17 H17 111.7 4_655 . ? N9 C18 N12 113.7(6) . . ? N9 C18 H18A 108.8 . . ? N12 C18 H18A 108.8 . . ? N9 C18 H18B 108.8 . . ? N12 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? O8 C19 N12 125.0(4) . . ? O8 C19 N12 125.0(4) . 4_655 ? N12 C19 N12 110.0(9) . 4_655 ? O7 C20 N11 126.8(4) . 4_655 ? O7 C20 N11 126.8(4) . . ? N11 C20 N11 106.5(8) 4_655 . ? C2E C1E H1EA 109.5 . . ? C2E C1E H1EB 109.5 . . ? H1EA C1E H1EB 109.5 . . ? C2E C1E H1EC 109.4 . . ? H1EA C1E H1EC 109.5 . . ? H1EB C1E H1EC 109.5 . . ? O3E C2E C1E 117(2) . . ? O3E C2E H2EA 108.0 . . ? C1E C2E H2EA 108.0 . . ? O3E C2E H2EB 108.0 . . ? C1E C2E H2EB 108.0 . . ? H2EA C2E H2EB 107.3 . . ? C2E O3E C4E 112(2) . . ? C5E C4E O3E 114(2) . . ? C5E C4E H4EA 108.8 . . ? O3E C4E H4EA 108.8 . . ? C5E C4E H4EB 108.8 . . ? O3E C4E H4EB 108.8 . . ? H4EA C4E H4EB 107.7 . . ? C4E C5E H5EA 109.5 . . ? C4E C5E H5EB 109.5 . . ? H5EA C5E H5EB 109.5 . . ? C4E C5E H5EC 109.5 . . ? H5EA C5E H5EC 109.5 . . ? H5EB C5E H5EC 109.5 . . ? H11W O1W H12W 110(3) . . ? H21W O2W H22W 109(3) . . ? H31W O3W H32W 109(3) . . ? H41W O4W H42W 109(3) . . ? 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 C5 N1 C1 O1 10.7(14) . . . . ? C2 N1 C1 O1 173.0(9) . . . . ? C5 N1 C1 N1 -169.0(5) . . . 4_655 ? C2 N1 C1 N1 -6.6(11) . . . 4_655 ? C3 N2 C2 N1 -118.4(8) . . . . ? C4 N2 C2 N1 78.9(8) . . . . ? C3 N2 C2 C2 -6.9(7) . . . 4_655 ? C4 N2 C2 C2 -169.6(5) . . . 4_655 ? C1 N1 C2 N2 115.6(7) . . . . ? C5 N1 C2 N2 -81.7(8) . . . . ? C1 N1 C2 C2 4.0(6) . . . 4_655 ? C5 N1 C2 C2 166.7(5) . . . 4_655 ? C4 N2 C3 O2 -4.9(14) . . . . ? C2 N2 C3 O2 -167.7(9) . . . . ? C4 N2 C3 N2 174.1(5) . . . 4_655 ? C2 N2 C3 N2 11.3(11) . . . 4_655 ? C3 N2 C4 N3 112.8(8) . . . . ? C2 N2 C4 N3 -86.1(8) . . . . ? C8 N3 C4 N2 -110.2(7) . . . . ? C7 N3 C4 N2 85.8(8) . . . . ? C6 N4 C5 N1 103.8(8) . . . . ? C7 N4 C5 N1 -83.1(9) . . . . ? C1 N1 C5 N4 -110.5(8) . . . . ? C2 N1 C5 N4 88.7(8) . . . . ? C9 N5 C6 O4 170.1(7) . . . . ? C10 N5 C6 O4 5.5(12) . . . . ? C9 N5 C6 N4 -7.8(9) . . . . ? C10 N5 C6 N4 -172.4(6) . . . . ? C7 N4 C6 O4 -173.2(7) . . . . ? C5 N4 C6 O4 0.7(12) . . . . ? C7 N4 C6 N5 4.7(8) . . . . ? C5 N4 C6 N5 178.6(6) . . . . ? C6 N4 C7 N3 -112.6(7) . . . . ? C5 N4 C7 N3 73.5(9) . . . . ? C6 N4 C7 C9 -0.1(8) . . . . ? C5 N4 C7 C9 -174.0(6) . . . . ? C8 N3 C7 N4 118.4(7) . . . . ? C4 N3 C7 N4 -76.1(8) . . . . ? C8 N3 C7 C9 5.5(7) . . . . ? C4 N3 C7 C9 170.9(6) . . . . ? C11 N6 C8 O3 4.1(10) . . . . ? C9 N6 C8 O3 -169.7(6) . . . . ? C11 N6 C8 N3 -178.9(6) . . . . ? C9 N6 C8 N3 7.3(8) . . . . ? C4 N3 C8 O3 3.4(10) . . . . ? C7 N3 C8 O3 168.9(6) . . . . ? C4 N3 C8 N6 -173.6(6) . . . . ? C7 N3 C8 N6 -8.1(8) . . . . ? C6 N5 C9 N6 118.8(7) . . . . ? C10 N5 C9 N6 -76.6(9) . . . . ? C6 N5 C9 C7 7.3(8) . . . . ? C10 N5 C9 C7 171.9(6) . . . . ? C8 N6 C9 N5 -114.9(7) . . . . ? C11 N6 C9 N5 71.4(8) . . . . ? C8 N6 C9 C7 -3.8(7) . . . . ? C11 N6 C9 C7 -177.4(6) . . . . ? N4 C7 C9 N5 -4.1(7) . . . . ? N3 C7 C9 N5 119.4(6) . . . . ? N4 C7 C9 N6 -124.5(6) . . . . ? N3 C7 C9 N6 -1.0(7) . . . . ? C14 N8 C10 N5 99.5(8) . . . . ? C13 N8 C10 N5 -86.3(8) . . . . ? C6 N5 C10 N8 -106.0(8) . . . . ? C9 N5 C10 N8 91.1(8) . . . . ? C8 N6 C11 N7 102.2(7) . . . . ? C9 N6 C11 N7 -84.8(8) . . . . ? C12 N7 C11 N6 -106.2(8) . . . . ? C13 N7 C11 N6 90.8(8) . . . . ? C16 N10 C12 O6 -1.1(12) . . . . ? C15 N10 C12 O6 -175.1(7) . . . . ? C16 N10 C12 N7 -179.9(6) . . . . ? C15 N10 C12 N7 6.1(8) . . . . ? C11 N7 C12 O6 7.9(12) . . . . ? C13 N7 C12 O6 172.8(7) . . . . ? C11 N7 C12 N10 -173.2(6) . . . . ? C13 N7 C12 N10 -8.3(8) . . . . ? C14 N8 C13 N7 -113.5(7) . . . . ? C10 N8 C13 N7 71.8(8) . . . . ? C14 N8 C13 C15 -1.5(7) . . . . ? C10 N8 C13 C15 -176.2(6) . . . . ? C12 N7 C13 N8 118.9(7) . . . . ? C11 N7 C13 N8 -76.7(9) . . . . ? C12 N7 C13 C15 7.1(8) . . . . ? C11 N7 C13 C15 171.5(6) . . . . ? C18 N9 C14 O5 8.0(10) . . . . ? C15 N9 C14 O5 168.9(7) . . . . ? C18 N9 C14 N8 -170.1(6) . . . . ? C15 N9 C14 N8 -9.2(8) . . . . ? C13 N8 C14 O5 -171.5(7) . . . . ? C10 N8 C14 O5 3.2(11) . . . . ? C13 N8 C14 N9 6.5(8) . . . . ? C10 N8 C14 N9 -178.7(6) . . . . ? C14 N9 C15 N10 119.3(6) . . . . ? C18 N9 C15 N10 -80.6(8) . . . . ? C14 N9 C15 C13 8.0(7) . . . . ? C18 N9 C15 C13 168.1(6) . . . . ? C12 N10 C15 N9 -113.2(7) . . . . ? C16 N10 C15 N9 72.9(8) . . . . ? C12 N10 C15 C13 -1.7(8) . . . . ? C16 N10 C15 C13 -175.5(6) . . . . ? N8 C13 C15 N9 -3.7(7) . . . . ? N7 C13 C15 N9 116.2(6) . . . . ? N8 C13 C15 N10 -123.1(6) . . . . ? N7 C13 C15 N10 -3.1(7) . . . . ? C12 N10 C16 N11 104.5(7) . . . . ? C15 N10 C16 N11 -82.2(8) . . . . ? C20 N11 C16 N10 -112.5(8) . . . . ? C17 N11 C16 N10 90.7(8) . . . . ? C20 N11 C17 N12 117.5(7) . . . . ? C16 N11 C17 N12 -84.0(8) . . . . ? C20 N11 C17 C17 6.2(6) . . . 4_655 ? C16 N11 C17 C17 164.7(5) . . . 4_655 ? C19 N12 C17 N11 -114.6(8) . . . . ? C18 N12 C17 N11 76.5(9) . . . . ? C19 N12 C17 C17 -3.0(7) . . . 4_655 ? C18 N12 C17 C17 -171.9(6) . . . 4_655 ? C14 N9 C18 N12 -110.4(7) . . . . ? C15 N9 C18 N12 91.1(8) . . . . ? C19 N12 C18 N9 109.3(9) . . . . ? C17 N12 C18 N9 -83.2(8) . . . . ? C17 N12 C19 O8 -173.0(9) . . . . ? C18 N12 C19 O8 -4.3(15) . . . . ? C17 N12 C19 N12 5.1(12) . . . 4_655 ? C18 N12 C19 N12 173.7(5) . . . 4_655 ? C17 N11 C20 O7 168.9(9) . . . . ? C16 N11 C20 O7 10.1(14) . . . . ? C17 N11 C20 N11 -10.1(10) . . . 4_655 ? C16 N11 C20 N11 -169.0(5) . . . 4_655 ? C1E C2E O3E C4E 162(7) . . . . ? C2E O3E C4E C5E -105(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.427 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.068