# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Binoy Krishna Saha' _publ_contact_author_address ;Assistant Professor Department of Chemistry Pondicherry University Puducherry-605 014 India ; _publ_contact_author_email binoypu@yahoo.co.in _publ_contact_author_phone '+91 4132654697' loop_ _publ_author_name _publ_author_address B.Saha ;Assistant Professor Department of Chemistry Pondicherry University Puducherry-605 014 India ; S.Bhattacharya ;Department of Chemistry Pondicherry University Puducherry-605 014 India ; _publ_section_title ; Inclusion of Chiral Guest in a Centrosymmetric Organic Host Lattice ; data_squeezed-r _database_code_depnum_ccdc_archive 'CCDC 822738' #TrackingRef '- combined-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-benzenetricarboxylic acid, 4,4'-bipyridine, (+/-) 2-methyl-1-butanol ; _chemical_name_common ; 2,4,6-triethyl-1,3,5-benzenetricarboxylic acid, 4,4'- bipyridine, (+/-) 2-methyl-1-butanol ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 O6, C10 H8 N2, C5 H12 O' _chemical_formula_sum 'C30 H38 N2 O7' _chemical_formula_weight 538.62 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0116(7) _cell_length_b 9.4080(6) _cell_length_c 18.0095(14) _cell_angle_alpha 83.760(6) _cell_angle_beta 76.517(7) _cell_angle_gamma 79.610(6) _cell_volume 1456.89(19) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4571 _cell_measurement_theta_min 2.8411 _cell_measurement_theta_max 29.2053 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11664 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 29.27 _reflns_number_total 6586 _reflns_number_gt 3877 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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. The 3 retrains have been used to refine the hydrogens attached to the oxygen atoms at a distance 0.85 and a nitrogen atom at a distance 0.91. The restaints are DFIX 0.85 0.01 O4 H4 DFIX 0.85 0.01 O5 H5 DFIX 0.91 0.01 N1 H1 SQUEEZE routine of PLATON was used to treat the residual electron density due to disordered guest molecules. ; _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^)+(0.1132P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6586 _refine_ls_number_parameters 310 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1785 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _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 C15 C 0.2000(3) -0.1721(2) 0.11922(14) 0.0621(6) Uani 1 1 d . . . H15A H 0.2200 -0.2406 0.0809 0.093 Uiso 1 1 calc R . . H15B H 0.1021 -0.1796 0.1533 0.093 Uiso 1 1 calc R . . H15C H 0.2802 -0.1924 0.1476 0.093 Uiso 1 1 calc R . . C11 C 0.4436(3) 0.4411(2) 0.16692(17) 0.0693(7) Uani 1 1 d . . . H11A H 0.5280 0.4744 0.1802 0.104 Uiso 1 1 calc R . . H11B H 0.3578 0.5187 0.1693 0.104 Uiso 1 1 calc R . . H11C H 0.4755 0.4091 0.1159 0.104 Uiso 1 1 calc R . . C13 C -0.2570(3) 0.2695(3) 0.32010(15) 0.0823(8) Uani 1 1 d . . . H13A H -0.3610 0.3178 0.3372 0.123 Uiso 1 1 calc R . . H13B H -0.1991 0.2714 0.3584 0.123 Uiso 1 1 calc R . . H13C H -0.2584 0.1709 0.3115 0.123 Uiso 1 1 calc R . . H4 H 0.057(4) 0.630(3) 0.2926(13) 0.119(12) Uiso 1 1 d D . . H5 H -0.254(3) 0.152(3) 0.0854(18) 0.112(12) Uiso 1 1 d D . . H1 H 0.633(3) -0.168(2) 0.1161(17) 0.129(12) Uiso 1 1 d D . . C2 C 0.2614(2) 0.25787(17) 0.20539(9) 0.0309(4) Uani 1 1 d . . . C6 C 0.1652(2) 0.09772(17) 0.13602(9) 0.0296(4) Uani 1 1 d . . . C3 C 0.1077(2) 0.32188(17) 0.23385(9) 0.0306(4) Uani 1 1 d . . . O2 O 0.54382(16) 0.12990(15) 0.08024(7) 0.0468(4) Uani 1 1 d . . . O1 O 0.48100(17) -0.05741(14) 0.16067(9) 0.0547(4) Uani 1 1 d . . . C1 C 0.28720(19) 0.14432(16) 0.15768(9) 0.0289(4) Uani 1 1 d . . . C4 C -0.0176(2) 0.27702(17) 0.21465(10) 0.0329(4) Uani 1 1 d . . . O4 O 0.0685(2) 0.56866(14) 0.25798(8) 0.0573(5) Uani 1 1 d D . . C8 C 0.0758(2) 0.43789(19) 0.28957(10) 0.0376(4) Uani 1 1 d . . . C5 C 0.0139(2) 0.16536(17) 0.16478(9) 0.0306(4) Uani 1 1 d . . . C7 C 0.4512(2) 0.06919(19) 0.12945(10) 0.0346(4) Uani 1 1 d . . . N1 N 0.7064(2) -0.24482(16) 0.09736(10) 0.0460(4) Uani 1 1 d D . . O5 O -0.1757(2) 0.18721(18) 0.09023(9) 0.0592(4) Uani 1 1 d D . . C9 C -0.1202(2) 0.1121(2) 0.14649(11) 0.0387(4) Uani 1 1 d . . . C14 C 0.1965(2) -0.02039(19) 0.08116(10) 0.0403(5) Uani 1 1 d . . . H14A H 0.2952 -0.0149 0.0460 0.048 Uiso 1 1 calc R . . H14B H 0.1174 -0.0024 0.0513 0.048 Uiso 1 1 calc R . . C10 C 0.3952(2) 0.3150(2) 0.22316(11) 0.0444(5) Uani 1 1 d . . . H10A H 0.4826 0.2373 0.2211 0.053 Uiso 1 1 calc R . . H10B H 0.3656 0.3471 0.2747 0.053 Uiso 1 1 calc R . . C18 C 0.9366(2) -0.44726(16) 0.02130(10) 0.0336(4) Uani 1 1 d . . . C12 C -0.1830(2) 0.3453(2) 0.24701(11) 0.0472(5) Uani 1 1 d . . . H12A H -0.1843 0.4453 0.2560 0.057 Uiso 1 1 calc R . . H12B H -0.2441 0.3453 0.2092 0.057 Uiso 1 1 calc R . . O3 O 0.0605(2) 0.40843(16) 0.35710(8) 0.0729(6) Uani 1 1 d . . . C19 C 0.9455(2) -0.3994(2) 0.08989(12) 0.0477(5) Uani 1 1 d . . . H19 H 1.0303 -0.4357 0.1114 0.057 Uiso 1 1 calc R . . N2 N 0.0405(3) 0.75845(19) 0.35703(10) 0.0646(6) Uani 1 1 d . . . O6 O -0.1725(2) 0.01035(18) 0.18101(11) 0.0734(5) Uani 1 1 d . . . C20 C 0.8290(3) -0.2982(2) 0.12634(13) 0.0541(6) Uani 1 1 d . . . H20 H 0.8364 -0.2666 0.1723 0.065 Uiso 1 1 calc R . . C23 C 0.0092(3) 0.9491(2) 0.46983(11) 0.0531(6) Uani 1 1 d . . . C17 C 0.8051(3) -0.3920(2) -0.00574(12) 0.0533(6) Uani 1 1 d . . . H17 H 0.7924 -0.4231 -0.0508 0.064 Uiso 1 1 calc R . . C16 C 0.6925(3) -0.2913(2) 0.03362(13) 0.0572(6) Uani 1 1 d . . . H16 H 0.6046 -0.2553 0.0146 0.069 Uiso 1 1 calc R . . C24 C 0.0356(4) 0.9937(2) 0.39387(12) 0.0757(9) Uani 1 1 d . . . H24 H 0.0442 1.0901 0.3785 0.091 Uiso 1 1 calc R . . C25 C 0.0494(4) 0.8962(2) 0.33994(12) 0.0834(10) Uani 1 1 d . . . H25 H 0.0660 0.9298 0.2886 0.100 Uiso 1 1 calc R . . C21 C 0.0182(4) 0.7141(3) 0.43008(13) 0.0888(11) Uani 1 1 d . . . H21 H 0.0130 0.6165 0.4435 0.107 Uiso 1 1 calc R . . C22 C 0.0021(4) 0.8043(2) 0.48758(13) 0.0891(11) Uani 1 1 d . . . H22 H -0.0136 0.7675 0.5384 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C15 0.0626(17) 0.0415(11) 0.0847(16) -0.0251(11) -0.0130(13) -0.0063(11) C11 0.0462(15) 0.0502(13) 0.120(2) -0.0078(13) -0.0291(14) -0.0142(11) C13 0.0453(16) 0.105(2) 0.0836(18) -0.0242(16) 0.0159(13) -0.0069(15) C2 0.0272(10) 0.0313(8) 0.0361(9) -0.0087(7) -0.0105(7) -0.0010(7) C6 0.0264(9) 0.0282(8) 0.0337(9) -0.0100(7) -0.0057(7) 0.0001(7) C3 0.0304(10) 0.0284(8) 0.0339(9) -0.0111(7) -0.0087(7) 0.0001(7) O2 0.0265(8) 0.0643(9) 0.0478(8) -0.0090(7) -0.0048(6) -0.0037(7) O1 0.0381(9) 0.0431(8) 0.0740(10) -0.0071(7) -0.0063(7) 0.0113(6) C1 0.0228(9) 0.0302(8) 0.0339(9) -0.0087(7) -0.0064(7) -0.0002(7) C4 0.0264(10) 0.0328(9) 0.0380(9) -0.0112(7) -0.0048(7) 0.0017(7) O4 0.0979(14) 0.0315(7) 0.0453(8) -0.0171(6) -0.0235(8) 0.0008(7) C8 0.0373(11) 0.0368(10) 0.0399(10) -0.0164(8) -0.0093(8) 0.0002(8) C5 0.0251(9) 0.0302(8) 0.0373(9) -0.0090(7) -0.0071(7) -0.0022(7) C7 0.0270(10) 0.0394(10) 0.0397(10) -0.0167(8) -0.0109(8) 0.0015(8) N1 0.0387(11) 0.0320(8) 0.0616(11) -0.0081(8) -0.0060(8) 0.0052(7) O5 0.0448(10) 0.0795(11) 0.0624(9) -0.0005(8) -0.0241(8) -0.0203(9) C9 0.0278(10) 0.0409(10) 0.0475(11) -0.0157(9) -0.0055(8) -0.0014(8) C14 0.0333(11) 0.0441(10) 0.0461(10) -0.0232(8) -0.0073(8) -0.0031(8) C10 0.0332(11) 0.0459(11) 0.0617(12) -0.0240(9) -0.0216(9) 0.0008(8) C18 0.0304(10) 0.0258(8) 0.0443(10) -0.0009(7) -0.0112(8) -0.0006(7) C12 0.0262(11) 0.0528(11) 0.0613(13) -0.0270(10) -0.0061(9) 0.0060(9) O3 0.1290(18) 0.0508(9) 0.0361(8) -0.0146(7) -0.0093(9) -0.0116(9) C19 0.0392(12) 0.0404(10) 0.0685(13) -0.0198(9) -0.0255(10) 0.0077(9) N2 0.1048(18) 0.0450(10) 0.0472(10) -0.0208(8) -0.0217(10) -0.0026(10) O6 0.0654(12) 0.0658(10) 0.1033(13) 0.0101(10) -0.0357(10) -0.0348(10) C20 0.0475(14) 0.0459(11) 0.0723(14) -0.0262(10) -0.0206(11) 0.0061(10) C23 0.0859(18) 0.0385(11) 0.0367(10) -0.0143(8) -0.0133(11) -0.0076(11) C17 0.0422(13) 0.0665(13) 0.0476(11) -0.0135(10) -0.0182(10) 0.0173(10) C16 0.0367(13) 0.0680(14) 0.0592(13) -0.0051(11) -0.0165(10) 0.0201(10) C24 0.145(3) 0.0404(12) 0.0396(12) -0.0123(9) -0.0189(14) -0.0052(14) C25 0.164(3) 0.0471(13) 0.0371(12) -0.0133(10) -0.0222(15) -0.0065(15) C21 0.174(4) 0.0448(13) 0.0520(14) -0.0162(11) -0.0173(17) -0.0306(16) C22 0.183(4) 0.0459(13) 0.0422(13) -0.0096(10) -0.0168(16) -0.0340(17) _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 C15 C14 1.513(3) . ? C11 C10 1.531(3) . ? C13 C12 1.498(3) . ? C2 C1 1.396(2) . ? C2 C3 1.406(2) . ? C2 C10 1.515(2) . ? C6 C5 1.400(2) . ? C6 C1 1.402(2) . ? C6 C14 1.512(2) . ? C3 C4 1.399(3) . ? C3 C8 1.507(2) . ? O2 C7 1.235(2) . ? O1 C7 1.271(2) . ? C1 C7 1.515(2) . ? C4 C5 1.403(2) . ? C4 C12 1.518(2) . ? O4 C8 1.295(2) . ? C8 O3 1.199(2) . ? C5 C9 1.503(3) . ? N1 C16 1.312(3) . ? N1 C20 1.325(3) . ? O5 C9 1.315(2) . ? C9 O6 1.192(2) . ? C18 C17 1.379(3) . ? C18 C19 1.384(3) . ? C18 C18 1.493(3) 2_745 ? C19 C20 1.376(3) . ? N2 C25 1.311(3) . ? N2 C21 1.316(3) . ? C23 C24 1.365(3) . ? C23 C22 1.374(3) . ? C23 C23 1.486(4) 2_576 ? C17 C16 1.376(3) . ? C24 C25 1.377(3) . ? C21 C22 1.375(3) . ? 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 C2 C3 118.09(16) . . ? C1 C2 C10 121.00(16) . . ? C3 C2 C10 120.86(15) . . ? C5 C6 C1 118.58(15) . . ? C5 C6 C14 120.72(16) . . ? C1 C6 C14 120.68(16) . . ? C4 C3 C2 122.07(15) . . ? C4 C3 C8 118.66(16) . . ? C2 C3 C8 119.21(16) . . ? C2 C1 C6 121.62(15) . . ? C2 C1 C7 118.92(15) . . ? C6 C1 C7 119.46(14) . . ? C3 C4 C5 117.95(16) . . ? C3 C4 C12 121.47(15) . . ? C5 C4 C12 120.58(17) . . ? O3 C8 O4 124.15(17) . . ? O3 C8 C3 121.54(16) . . ? O4 C8 C3 114.31(15) . . ? C6 C5 C4 121.65(16) . . ? C6 C5 C9 119.92(15) . . ? C4 C5 C9 118.31(15) . . ? O2 C7 O1 125.11(17) . . ? O2 C7 C1 120.83(16) . . ? O1 C7 C1 114.07(16) . . ? C16 N1 C20 119.88(18) . . ? O6 C9 O5 122.92(19) . . ? O6 C9 C5 122.28(18) . . ? O5 C9 C5 114.80(17) . . ? C6 C14 C15 114.45(16) . . ? C2 C10 C11 112.03(17) . . ? C17 C18 C19 116.64(17) . . ? C17 C18 C18 121.9(2) . 2_745 ? C19 C18 C18 121.5(2) . 2_745 ? C13 C12 C4 113.78(18) . . ? C20 C19 C18 120.04(19) . . ? C25 N2 C21 116.74(17) . . ? N1 C20 C19 121.4(2) . . ? C24 C23 C22 116.32(18) . . ? C24 C23 C23 122.0(2) . 2_576 ? C22 C23 C23 121.7(2) . 2_576 ? C16 C17 C18 120.4(2) . . ? N1 C16 C17 121.5(2) . . ? C23 C24 C25 120.1(2) . . ? N2 C25 C24 123.5(2) . . ? N2 C21 C22 123.5(2) . . ? C23 C22 C21 119.8(2) . . ? _diffrn_measured_fraction_theta_max 0.829 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.286 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.052 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.447 0.500 408 44 ' ' _platon_squeeze_details ; ; data_bks257-cg-p1 _database_code_depnum_ccdc_archive 'CCDC 822739' #TrackingRef '- combined-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-benzenetricarboxylic acid, 4,4'-bipyridine, (S)2-methyl-1-butanol ; _chemical_name_common ; 2,4,6-triethyl-1,3,5-benzenetricarboxylic acid, 4,4'- bipyridine, (S)2-methyl-1-butanol ; _chemical_melting_point ? _chemical_formula_moiety '2 C15 H18 O6, 2 C10 H8 N2, 2 C5 H12 O' _chemical_formula_sum 'C60 H76 N4 O14' _chemical_formula_weight 1077.25 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 triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.9857(2) _cell_length_b 9.4136(2) _cell_length_c 17.9866(4) _cell_angle_alpha 83.674(2) _cell_angle_beta 76.620(2) _cell_angle_gamma 79.597(2) _cell_volume 1452.09(6) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 21592 _cell_measurement_theta_min 2.8450 _cell_measurement_theta_max 29.2881 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9658 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51666 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 29.35 _reflns_number_total 14074 _reflns_number_gt 8854 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. The 9 retrains have been used to refine the hydrogens attached to the oxygen atoms at a distance 0.85 and a nitrogen atom at a distance 0.91. The restaints are DFIX 0.85 0.01 O4X H4X DFIX 0.85 0.01 O4 H4 DFIX 0.85 0.01 O5X H5X DFIX 0.91 0.01 N1 H1 DFIX 0.85 0.01 O1X H1X DFIX 0.85 0.01 O5 H5 DANG 1.8 0.02 C8 H4 DANG 1.81 0.02 C7X H1X DANG 1.81 0.02 C9 H5 SQUEEZE routine of PLATON was used to treat the residual electron density due to disordered guest molecules. H4 and H5 have been refined with Uiso(H) = 1.5Ueq(O/N) ; _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^)+(0.0987P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(11) _refine_ls_number_reflns 14074 _refine_ls_number_parameters 615 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _refine_ls_shift/su_max 0.002 _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 C10 C 0.4711(4) 0.6038(4) 0.1436(2) 0.0425(9) Uani 1 1 d . . . H10A H 0.5024 0.5711 0.0922 0.051 Uiso 1 1 calc R . . H10B H 0.3839 0.6817 0.1446 0.051 Uiso 1 1 calc R . . C11 C 0.4204(5) 0.4799(4) 0.1992(3) 0.0695(14) Uani 1 1 d . . . H11A H 0.3373 0.4463 0.1845 0.104 Uiso 1 1 calc R . . H11B H 0.3856 0.5126 0.2499 0.104 Uiso 1 1 calc R . . H11C H 0.5061 0.4023 0.1982 0.104 Uiso 1 1 calc R . . N2 N 0.8275(5) 0.1605(4) 0.0089(2) 0.0644(10) Uani 1 1 d . . . C23 C 0.8573(5) -0.0298(4) -0.1028(2) 0.0520(11) Uani 1 1 d . . . C24 C 0.8262(6) -0.0704(4) -0.0266(3) 0.0701(14) Uani 1 1 d . . . H24 H 0.8169 -0.1664 -0.0109 0.084 Uiso 1 1 calc R . . C25 C 0.8089(7) 0.0225(5) 0.0257(2) 0.0830(16) Uani 1 1 d . . . H25 H 0.7824 -0.0101 0.0770 0.100 Uiso 1 1 calc R . . C22 C 0.8627(7) 0.1128(4) -0.1218(2) 0.0871(18) Uani 1 1 d . . . H22 H 0.8727 0.1501 -0.1725 0.104 Uiso 1 1 calc R . . C21 C 0.8525(8) 0.2050(5) -0.0617(3) 0.098(2) Uani 1 1 d . . . H21 H 0.8647 0.3012 -0.0749 0.117 Uiso 1 1 calc R . . C6 C 0.7014(3) 0.8218(3) 0.23149(18) 0.0284(7) Uani 1 1 d . . . C1X C -0.8446(3) 2.0641(3) 0.52476(17) 0.0275(7) Uani 1 1 d . . . O2 O 0.3228(3) 0.7877(3) 0.28651(14) 0.0466(7) Uani 1 1 d . . . C6X C -0.9675(4) 2.0175(3) 0.50331(18) 0.0305(7) Uani 1 1 d . . . C4 C 0.8832(3) 0.6438(4) 0.15318(19) 0.0336(8) Uani 1 1 d . . . C2X C -0.8736(4) 2.1779(3) 0.5729(2) 0.0322(7) Uani 1 1 d . . . C3 C 0.7620(4) 0.5991(3) 0.1320(2) 0.0353(8) Uani 1 1 d . . . C2 C 0.6040(3) 0.6614(3) 0.16212(19) 0.0294(7) Uani 1 1 d . . . C1 C 0.5806(3) 0.7739(3) 0.20964(18) 0.0319(8) Uani 1 1 d . . . C3X C -1.0228(4) 2.2425(3) 0.59974(17) 0.0280(7) Uani 1 1 d . . . C5X C -1.1191(4) 2.0852(3) 0.53060(17) 0.0291(7) Uani 1 1 d . . . O1 O 0.3862(3) 0.9738(3) 0.20623(17) 0.0568(8) Uani 1 1 d . . . C4X C -1.1513(4) 2.1981(3) 0.58190(18) 0.0326(7) Uani 1 1 d . . . O1X O -0.6515(3) 1.8600(2) 0.52784(15) 0.0502(7) Uani 1 1 d D . . O2X O -0.5890(3) 2.0485(3) 0.44699(14) 0.0444(6) Uani 1 1 d . . . C7X C -0.6799(4) 1.9876(3) 0.49559(19) 0.0342(8) Uani 1 1 d D . . C5 C 0.8524(3) 0.7531(3) 0.20097(19) 0.0328(8) Uani 1 1 d . . . O4 O 0.7981(4) 0.3513(3) 0.10859(15) 0.0580(8) Uani 1 1 d D . . O4X O -1.0635(4) 2.4890(3) 0.62427(15) 0.0564(8) Uani 1 1 d D . . C8X C -1.0558(4) 2.3589(3) 0.6568(2) 0.0396(9) Uani 1 1 d . . . C7 C 0.4162(4) 0.8488(3) 0.2368(2) 0.0340(8) Uani 1 1 d . . . N1 N 0.1623(3) 1.1627(3) 0.2694(2) 0.0454(8) Uani 1 1 d D . . C9X C -1.2521(4) 2.0320(4) 0.5133(2) 0.0434(9) Uani 1 1 d . . . C8 C 0.7912(4) 0.4836(4) 0.0777(2) 0.0349(8) Uani 1 1 d D . . O5 O 1.0449(3) 0.7300(3) 0.27485(18) 0.0596(7) Uani 1 1 d D . . C14X C -0.9357(4) 1.8967(4) 0.4484(2) 0.0403(9) Uani 1 1 d . . . H14C H -1.0155 1.9140 0.4187 0.048 Uiso 1 1 calc R . . H14D H -0.8373 1.9026 0.4129 0.048 Uiso 1 1 calc R . . C18X C -0.1953(4) 1.4698(3) 0.3874(2) 0.0356(8) Uani 1 1 d . . . N1X N -0.4253(3) 1.6740(3) 0.46460(19) 0.0456(8) Uani 1 1 d . . . C18 C -0.0689(3) 1.3647(3) 0.3447(2) 0.0318(7) Uani 1 1 d . . . C9 C 0.9876(3) 0.8079(4) 0.22041(19) 0.0343(8) Uani 1 1 d D . . O5X O -1.3066(3) 2.1046(3) 0.45565(16) 0.0551(7) Uani 1 1 d D . . C10X C -0.7384(4) 2.2355(4) 0.5903(2) 0.0470(10) Uani 1 1 d . . . H10C H -0.6498 2.1586 0.5874 0.056 Uiso 1 1 calc R . . H10D H -0.7667 2.2673 0.6419 0.056 Uiso 1 1 calc R . . C14 C 0.6707(4) 0.9375(4) 0.2859(2) 0.0399(8) Uani 1 1 d . . . H14A H 0.7500 0.9192 0.3159 0.048 Uiso 1 1 calc R . . H14B H 0.5718 0.9322 0.3210 0.048 Uiso 1 1 calc R . . C16X C -0.4371(4) 1.6279(4) 0.3981(2) 0.0566(11) Uani 1 1 d . . . H16X H -0.5239 1.6651 0.3781 0.068 Uiso 1 1 calc R . . C19 C -0.0789(4) 1.3165(4) 0.2779(2) 0.0491(10) Uani 1 1 d . . . H19 H -0.1666 1.3508 0.2580 0.059 Uiso 1 1 calc R . . O3X O -1.0714(4) 2.3290(3) 0.72429(15) 0.0692(10) Uani 1 1 d . . . O3 O 0.8074(4) 0.5127(3) 0.01018(17) 0.0771(10) Uani 1 1 d . . . C12X C -1.3134(4) 2.2622(4) 0.6143(2) 0.0451(9) Uani 1 1 d . . . H12C H -1.3155 2.3626 0.6228 0.054 Uiso 1 1 calc R . . H12D H -1.3747 2.2614 0.5766 0.054 Uiso 1 1 calc R . . O6X O -1.3097(4) 1.9312(3) 0.54945(18) 0.0703(9) Uani 1 1 d . . . C12 C 1.0508(4) 0.5712(4) 0.1212(2) 0.0482(10) Uani 1 1 d . . . H12A H 1.0505 0.4719 0.1116 0.058 Uiso 1 1 calc R . . H12B H 1.1123 0.5695 0.1591 0.058 Uiso 1 1 calc R . . C19X C -0.1875(4) 1.5187(4) 0.4573(2) 0.0458(10) Uani 1 1 d . . . H19X H -0.1048 1.4810 0.4803 0.055 Uiso 1 1 calc R . . C13X C -1.3850(5) 2.1926(6) 0.6838(3) 0.0859(16) Uani 1 1 d . . . H13D H -1.4882 2.2431 0.7009 0.129 Uiso 1 1 calc R . . H13E H -1.3260 2.1930 0.7220 0.129 Uiso 1 1 calc R . . H13F H -1.3894 2.0945 0.6757 0.129 Uiso 1 1 calc R . . C20 C 0.0341(5) 1.2210(4) 0.2398(2) 0.0516(10) Uani 1 1 d . . . H20 H 0.0261 1.1937 0.1929 0.062 Uiso 1 1 calc R . . O6 O 1.0358(3) 0.9110(3) 0.1871(2) 0.0730(9) Uani 1 1 d . . . N2X N 0.9082(5) -0.3211(4) -0.27712(19) 0.0649(11) Uani 1 1 d . . . C20X C -0.3064(5) 1.6252(4) 0.4919(3) 0.0544(11) Uani 1 1 d . . . H20X H -0.2975 1.6613 0.5365 0.065 Uiso 1 1 calc R . . C17 C 0.0625(5) 1.3167(5) 0.3724(2) 0.0606(12) Uani 1 1 d . . . H17 H 0.0770 1.3519 0.4161 0.073 Uiso 1 1 calc R . . C21X C 0.8909(7) -0.3665(5) -0.2017(3) 0.0821(16) Uani 1 1 d . . . H21X H 0.8947 -0.4650 -0.1879 0.098 Uiso 1 1 calc R . . C23X C 0.8760(5) -0.1320(4) -0.1632(2) 0.0538(11) Uani 1 1 d . . . C15 C 0.6678(4) 1.0911(4) 0.2469(2) 0.0580(11) Uani 1 1 d . . . H15A H 0.6471 1.1598 0.2852 0.087 Uiso 1 1 calc R . . H15B H 0.5880 1.1111 0.2180 0.087 Uiso 1 1 calc R . . H15C H 0.7663 1.0984 0.2132 0.087 Uiso 1 1 calc R . . C15X C -0.9307(5) 1.7465(4) 0.4859(3) 0.0659(13) Uani 1 1 d . . . H15D H -0.9108 1.6783 0.4474 0.099 Uiso 1 1 calc R . . H15E H -1.0283 1.7381 0.5202 0.099 Uiso 1 1 calc R . . H15F H -0.8497 1.7265 0.5140 0.099 Uiso 1 1 calc R . . C22X C 0.8690(8) -0.2774(5) -0.1472(3) 0.095(2) Uani 1 1 d . . . H22X H 0.8482 -0.3138 -0.0963 0.114 Uiso 1 1 calc R . . C17X C -0.3288(4) 1.5314(4) 0.3609(2) 0.0463(9) Uani 1 1 d . . . H17X H -0.3415 1.5032 0.3151 0.056 Uiso 1 1 calc R . . C16 C 0.1770(4) 1.2096(4) 0.3310(2) 0.0535(11) Uani 1 1 d . . . H16 H 0.2655 1.1729 0.3498 0.064 Uiso 1 1 calc R . . C11X C -0.6938(5) 2.3637(4) 0.5327(3) 0.0675(13) Uani 1 1 d . . . H11D H -0.6080 2.3978 0.5444 0.101 Uiso 1 1 calc R . . H11E H -0.7807 2.4406 0.5363 0.101 Uiso 1 1 calc R . . H11F H -0.6651 2.3320 0.4816 0.101 Uiso 1 1 calc R . . C24X C 0.8983(7) -0.0820(4) -0.2397(2) 0.0781(16) Uani 1 1 d . . . H24X H 0.9073 0.0142 -0.2551 0.094 Uiso 1 1 calc R . . C13 C 1.1270(5) 0.6535(5) 0.0448(2) 0.0733(14) Uani 1 1 d . . . H13A H 1.2320 0.6072 0.0275 0.110 Uiso 1 1 calc R . . H13B H 1.1261 0.7522 0.0539 0.110 Uiso 1 1 calc R . . H13C H 1.0693 0.6511 0.0063 0.110 Uiso 1 1 calc R . . C25X C 0.9067(7) -0.1851(5) -0.2941(2) 0.0775(15) Uani 1 1 d . . . H25X H 0.9114 -0.1512 -0.3451 0.093 Uiso 1 1 calc R . . H5 H 1.1294 0.7512 0.2806 0.116 Uiso 0.17(7) 1 d PD . . H4X H -1.076(6) 2.547(3) 0.6605(15) 0.103(11) Uiso 1 1 d D . . H4 H 0.815(9) 0.290(2) 0.0743(15) 0.154 Uiso 1 1 d D . . H5X H -1.3930(14) 2.0763(17) 0.4530(9) 0.018(4) Uiso 1 1 d D . . H1X H -0.582(3) 1.803(2) 0.4984(13) 0.095(10) Uiso 1 1 d D . . H1 H 0.232(2) 1.0926(17) 0.2432(10) 0.037(5) 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 C10 0.0320(18) 0.043(2) 0.061(2) -0.0140(17) -0.0237(17) -0.0044(15) C11 0.044(2) 0.042(2) 0.132(4) -0.001(2) -0.040(2) -0.0066(17) N2 0.102(3) 0.0425(19) 0.048(2) -0.0227(16) -0.016(2) 0.0004(19) C23 0.074(3) 0.0350(19) 0.047(2) -0.0180(17) -0.007(2) -0.0069(18) C24 0.127(4) 0.0313(19) 0.050(3) -0.0024(17) -0.016(2) -0.012(2) C25 0.165(5) 0.045(2) 0.038(2) -0.0051(18) -0.014(3) -0.024(3) C22 0.194(6) 0.033(2) 0.040(2) -0.0113(17) -0.034(3) -0.017(3) C21 0.200(6) 0.052(2) 0.046(3) -0.029(2) -0.006(3) -0.046(3) C6 0.0182(13) 0.0319(16) 0.0351(17) -0.0049(13) -0.0052(12) -0.0028(12) C1X 0.0207(15) 0.0307(16) 0.0305(17) -0.0059(13) -0.0072(13) 0.0014(12) O2 0.0252(12) 0.0659(17) 0.0480(16) -0.0108(14) -0.0049(11) -0.0057(12) C6X 0.0348(17) 0.0228(15) 0.0340(17) -0.0134(13) -0.0066(14) 0.0008(12) C4 0.0121(12) 0.0454(18) 0.0390(18) -0.0111(14) 0.0000(12) 0.0044(12) C2X 0.0363(18) 0.0244(16) 0.0399(18) -0.0090(14) -0.0150(15) -0.0027(13) C3 0.0306(16) 0.0324(18) 0.0407(19) -0.0124(15) -0.0042(14) 0.0027(13) C2 0.0187(14) 0.0334(17) 0.0353(17) -0.0075(14) -0.0070(12) 0.0024(12) C1 0.0278(17) 0.0276(16) 0.039(2) -0.0098(14) -0.0054(15) 0.0004(13) C3X 0.0328(16) 0.0249(16) 0.0284(16) -0.0068(12) -0.0103(13) -0.0027(12) C5X 0.0292(16) 0.0292(16) 0.0279(16) -0.0075(13) -0.0051(13) -0.0005(13) O1 0.0368(15) 0.0451(16) 0.080(2) -0.0040(15) -0.0056(14) 0.0075(12) C4X 0.0436(18) 0.0181(13) 0.0381(18) -0.0099(12) -0.0119(15) -0.0011(12) O1X 0.0389(14) 0.0343(14) 0.0688(19) -0.0100(13) -0.0071(13) 0.0143(11) O2X 0.0279(12) 0.0563(16) 0.0465(15) -0.0060(13) -0.0061(12) -0.0012(11) C7X 0.0269(17) 0.0385(19) 0.0371(19) -0.0186(15) -0.0082(15) 0.0060(14) C5 0.0196(15) 0.0308(17) 0.050(2) -0.0110(15) -0.0082(14) -0.0043(13) O4 0.101(2) 0.0329(14) 0.0449(16) -0.0142(12) -0.0269(16) -0.0023(14) O4X 0.097(2) 0.0288(13) 0.0454(16) -0.0157(11) -0.0228(16) 0.0036(13) C8X 0.045(2) 0.0272(17) 0.047(2) -0.0177(15) -0.0072(17) -0.0041(14) C7 0.0244(16) 0.0371(19) 0.044(2) -0.0128(15) -0.0115(15) -0.0036(14) N1 0.0397(18) 0.0306(16) 0.061(2) -0.0098(15) -0.0080(15) 0.0079(13) C9X 0.0430(19) 0.0315(18) 0.051(2) -0.0147(16) -0.0087(17) 0.0110(15) C8 0.0311(17) 0.0419(19) 0.0320(18) -0.0122(15) -0.0107(14) 0.0039(14) O5 0.0518(16) 0.0677(18) 0.0697(18) 0.0066(15) -0.0294(14) -0.0228(14) C14X 0.0377(19) 0.0429(19) 0.0427(19) -0.0282(16) -0.0086(16) 0.0028(15) C18X 0.0389(18) 0.0271(16) 0.043(2) -0.0004(14) -0.0126(15) -0.0075(13) N1X 0.0390(18) 0.0310(16) 0.061(2) -0.0049(15) -0.0037(15) 0.0011(13) C18 0.0229(15) 0.0218(14) 0.045(2) -0.0002(13) -0.0061(14) 0.0077(12) C9 0.0164(13) 0.048(2) 0.044(2) -0.0164(16) -0.0052(13) -0.0130(13) O5X 0.0365(14) 0.0830(19) 0.0532(15) -0.0052(14) -0.0186(12) -0.0171(13) C10X 0.037(2) 0.045(2) 0.066(3) -0.0302(19) -0.0195(18) 0.0040(16) C14 0.0302(18) 0.0408(19) 0.050(2) -0.0162(16) -0.0042(16) -0.0074(14) C16X 0.047(2) 0.072(3) 0.047(2) -0.001(2) -0.0172(18) 0.007(2) C19 0.038(2) 0.043(2) 0.074(3) -0.027(2) -0.025(2) 0.0044(17) O3X 0.135(3) 0.0387(15) 0.0346(16) -0.0066(12) -0.0184(17) -0.0121(16) O3 0.127(3) 0.0586(19) 0.0417(17) -0.0185(14) -0.0051(17) -0.0125(18) C12X 0.0357(19) 0.044(2) 0.056(2) -0.0193(17) -0.0107(17) 0.0024(15) O6X 0.071(2) 0.072(2) 0.079(2) 0.0204(16) -0.0299(16) -0.0394(16) C12 0.0217(17) 0.056(2) 0.063(2) -0.0302(19) -0.0005(16) 0.0082(15) C19X 0.040(2) 0.0361(19) 0.063(3) -0.0115(18) -0.0236(19) 0.0100(16) C13X 0.050(3) 0.093(3) 0.105(4) -0.021(3) 0.000(3) 0.000(2) C20 0.053(2) 0.047(2) 0.060(2) -0.0165(17) -0.0257(18) 0.0041(17) O6 0.0528(17) 0.0540(17) 0.128(3) -0.0019(17) -0.0399(17) -0.0267(14) N2X 0.110(3) 0.0427(19) 0.046(2) -0.0169(16) -0.024(2) -0.007(2) C20X 0.043(2) 0.0385(19) 0.082(3) -0.0337(19) -0.0137(19) 0.0095(16) C17 0.051(2) 0.076(3) 0.045(2) -0.017(2) -0.0129(18) 0.026(2) C21X 0.154(5) 0.040(2) 0.058(3) -0.0023(19) -0.029(3) -0.022(3) C23X 0.091(3) 0.041(2) 0.0314(19) -0.0090(16) -0.020(2) -0.003(2) C15 0.050(2) 0.052(2) 0.076(3) -0.025(2) -0.020(2) 0.0012(18) C15X 0.079(3) 0.0287(18) 0.091(3) -0.0261(19) -0.007(2) -0.0145(18) C22X 0.182(6) 0.063(3) 0.042(3) -0.009(2) 0.002(3) -0.059(3) C17X 0.0381(19) 0.0509(19) 0.051(2) -0.0081(17) -0.0235(17) 0.0101(15) C16 0.0293(18) 0.053(2) 0.066(3) -0.005(2) -0.0118(17) 0.0256(17) C11X 0.049(2) 0.057(3) 0.105(4) -0.007(2) -0.019(2) -0.0246(19) C24X 0.160(5) 0.036(2) 0.033(2) -0.0164(16) -0.020(2) 0.004(2) C13 0.039(2) 0.102(3) 0.065(3) -0.019(2) 0.0277(19) -0.015(2) C25X 0.147(4) 0.047(2) 0.038(2) -0.0182(18) -0.033(2) 0.011(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 C10 C2 1.512(4) . ? C10 C11 1.514(6) . ? N2 C21 1.274(6) . ? N2 C25 1.333(5) . ? C23 C22 1.355(5) . ? C23 C24 1.360(6) . ? C23 C23X 1.490(2) . ? C24 C25 1.318(5) . ? C22 C21 1.436(5) . ? C6 C1 1.396(4) . ? C6 C5 1.406(4) . ? C6 C14 1.490(4) . ? C1X C2X 1.401(4) . ? C1X C6X 1.404(4) . ? C1X C7X 1.524(4) . ? O2 C7 1.245(4) . ? C6X C5X 1.396(4) . ? C6X C14X 1.533(4) . ? C4 C5 1.362(4) . ? C4 C3 1.379(4) . ? C4 C12 1.543(4) . ? C2X C3X 1.368(4) . ? C2X C10X 1.523(5) . ? C3 C2 1.438(4) . ? C3 C8 1.488(4) . ? C2 C1 1.390(4) . ? C1 C7 1.512(4) . ? C3X C4X 1.410(4) . ? C3X C8X 1.526(4) . ? C5X C4X 1.431(4) . ? C5X C9X 1.482(5) . ? O1 C7 1.253(4) . ? C4X C12X 1.481(4) . ? O1X C7X 1.284(4) . ? O2X C7X 1.220(4) . ? C5 C9 1.525(4) . ? O4 C8 1.304(4) . ? O4X C8X 1.296(4) . ? C8X O3X 1.197(5) . ? N1 C16 1.280(5) . ? N1 C20 1.379(5) . ? C9X O6X 1.216(4) . ? C9X O5X 1.319(4) . ? C8 O3 1.196(4) . ? O5 C9 1.304(4) . ? C14X C15X 1.496(5) . ? C18X C17X 1.398(4) . ? C18X C19X 1.407(5) . ? C18X C18 1.4882(19) . ? N1X C20X 1.268(5) . ? N1X C16X 1.349(5) . ? C18 C19 1.358(5) . ? C18 C17 1.370(5) . ? C9 O6 1.180(4) . ? C10X C11X 1.548(6) . ? C14 C15 1.534(5) . ? C16X C17X 1.316(5) . ? C19 C20 1.339(5) . ? C12X C13X 1.416(6) . ? C12 C13 1.575(6) . ? C19X C20X 1.406(4) . ? N2X C25X 1.281(5) . ? N2X C21X 1.358(6) . ? C17 C16 1.437(5) . ? C21X C22X 1.318(6) . ? C23X C22X 1.376(6) . ? C23X C24X 1.386(5) . ? C24X C25X 1.433(5) . ? 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 C10 C11 112.7(3) . . ? C21 N2 C25 117.0(4) . . ? C22 C23 C24 116.1(4) . . ? C22 C23 C23X 120.7(3) . . ? C24 C23 C23X 123.1(3) . . ? C25 C24 C23 122.0(4) . . ? C24 C25 N2 123.4(4) . . ? C23 C22 C21 118.3(4) . . ? N2 C21 C22 122.7(4) . . ? C1 C6 C5 116.6(3) . . ? C1 C6 C14 121.4(3) . . ? C5 C6 C14 122.0(3) . . ? C2X C1X C6X 120.4(3) . . ? C2X C1X C7X 120.8(3) . . ? C6X C1X C7X 118.9(3) . . ? C5X C6X C1X 119.4(3) . . ? C5X C6X C14X 120.1(3) . . ? C1X C6X C14X 120.5(3) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 C12 121.3(3) . . ? C3 C4 C12 119.4(3) . . ? C3X C2X C1X 119.7(3) . . ? C3X C2X C10X 120.4(3) . . ? C1X C2X C10X 119.7(3) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 C8 120.8(3) . . ? C2 C3 C8 118.1(3) . . ? C1 C2 C3 116.8(3) . . ? C1 C2 C10 122.4(3) . . ? C3 C2 C10 120.8(3) . . ? C2 C1 C6 123.1(3) . . ? C2 C1 C7 117.6(3) . . ? C6 C1 C7 119.3(3) . . ? C2X C3X C4X 122.6(3) . . ? C2X C3X C8X 119.8(3) . . ? C4X C3X C8X 117.4(3) . . ? C6X C5X C4X 121.0(3) . . ? C6X C5X C9X 120.7(3) . . ? C4X C5X C9X 118.1(3) . . ? C3X C4X C5X 116.9(3) . . ? C3X C4X C12X 122.8(3) . . ? C5X C4X C12X 120.3(3) . . ? O2X C7X O1X 126.3(3) . . ? O2X C7X C1X 120.4(3) . . ? O1X C7X C1X 113.3(3) . . ? C4 C5 C6 123.1(3) . . ? C4 C5 C9 118.9(3) . . ? C6 C5 C9 118.0(3) . . ? O3X C8X O4X 125.1(3) . . ? O3X C8X C3X 121.9(3) . . ? O4X C8X C3X 113.0(3) . . ? O2 C7 O1 124.8(3) . . ? O2 C7 C1 120.6(3) . . ? O1 C7 C1 114.6(3) . . ? C16 N1 C20 118.8(3) . . ? O6X C9X O5X 121.6(4) . . ? O6X C9X C5X 123.6(3) . . ? O5X C9X C5X 114.7(3) . . ? O3 C8 O4 123.1(3) . . ? O3 C8 C3 121.1(3) . . ? O4 C8 C3 115.8(3) . . ? C15X C14X C6X 115.2(3) . . ? C17X C18X C19X 114.3(3) . . ? C17X C18X C18 123.4(2) . . ? C19X C18X C18 122.2(2) . . ? C20X N1X C16X 119.6(3) . . ? C19 C18 C17 118.7(3) . . ? C19 C18 C18X 121.7(2) . . ? C17 C18 C18X 119.6(2) . . ? O6 C9 O5 124.1(3) . . ? O6 C9 C5 121.5(3) . . ? O5 C9 C5 114.4(3) . . ? C2X C10X C11X 110.8(3) . . ? C6 C14 C15 113.9(3) . . ? C17X C16X N1X 121.7(3) . . ? C20 C19 C18 121.7(3) . . ? C13X C12X C4X 115.6(3) . . ? C4 C12 C13 111.8(3) . . ? C20X C19X C18X 119.1(3) . . ? C19 C20 N1 120.7(4) . . ? C25X N2X C21X 116.7(4) . . ? N1X C20X C19X 122.6(4) . . ? C18 C17 C16 117.1(4) . . ? C22X C21X N2X 123.1(4) . . ? C22X C23X C24X 116.5(4) . . ? C22X C23X C23 123.2(3) . . ? C24X C23X C23 120.2(3) . . ? C21X C22X C23X 122.0(4) . . ? C16X C17X C18X 122.6(4) . . ? N1 C16 C17 122.7(3) . . ? C23X C24X C25X 117.1(4) . . ? N2X C25X C24X 124.2(4) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.275 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.051 # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.368 0.271 -0.134 408 44 ' ' _platon_squeeze_details ; ; data_bks258b-teb4-bpy-c_p21n _database_code_depnum_ccdc_archive 'CCDC 822740' #TrackingRef '- combined-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-benzenetricarboxylic acid, 4,4'-bipyridine, ; _chemical_name_common ;2,4,6-triethyl-1,3,5-benzenetricarboxylic acid, 4,4'- bipyridine, ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 O6, C10 H8 N2' _chemical_formula_sum 'C25 H26 N2 O6' _chemical_formula_weight 450.48 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4001(11) _cell_length_b 17.4597(16) _cell_length_c 11.6727(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.406(9) _cell_angle_gamma 90.00 _cell_volume 2277.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4359 _cell_measurement_theta_min 2.7827 _cell_measurement_theta_max 29.1722 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos' _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 15057 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 29.24 _reflns_number_total 5311 _reflns_number_gt 2970 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. The 5 retrains have been used to refine the hydrogens attached to the oxygen atoms at a distance 0.85 and a nitrogen atom at a distance 0.91. The restaints are DFIX 0.85 0.01 O2 H2 DFIX 0.91 0.01 N2 H2a DFIX 0.85 0.01 O4 H4 DANG 1.84 0.02 C8 H4 DFIX 0.85 0.01 O6 H6 SQUEEZE routine of PLATON was used to treat the residual electron density due to disordered guest molecules. H4 and H5 have been refined with Uiso(H) = 1.5Ueq(O/N) ; _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^)+(0.1087P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5311 _refine_ls_number_parameters 314 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1122 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1967 _refine_ls_wR_factor_gt 0.1799 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.049 _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 O5 O 0.71089(15) 0.14157(11) 0.72229(14) 0.0521(5) Uani 1 1 d . . . O6 O 0.60778(16) 0.05704(10) 0.60073(15) 0.0475(5) Uani 1 1 d D . . C5 C 0.49982(19) 0.15177(12) 0.67873(17) 0.0312(5) Uani 1 1 d . . . C7 C 0.3005(2) 0.17411(13) 0.90086(19) 0.0375(5) Uani 1 1 d . . . O2 O 0.24857(19) 0.10855(11) 0.90566(16) 0.0608(6) Uani 1 1 d D . . N2 N 0.71644(18) 0.53937(12) 0.00143(17) 0.0431(5) Uani 1 1 d D . . N1 N 0.3361(2) 0.58478(12) 0.40540(18) 0.0483(5) Uani 1 1 d . . . O1 O 0.3092(2) 0.22212(11) 0.97562(16) 0.0652(6) Uani 1 1 d . . . C4 C 0.4431(2) 0.19749(12) 0.58606(17) 0.0328(5) Uani 1 1 d . . . C2 C 0.2953(2) 0.23421(13) 0.70363(19) 0.0379(5) Uani 1 1 d . . . C23 C 0.56275(19) 0.55489(12) 0.15765(18) 0.0326(5) Uani 1 1 d . . . C9 C 0.6162(2) 0.11470(13) 0.66943(17) 0.0342(5) Uani 1 1 d . . . C6 C 0.45283(19) 0.14282(12) 0.78083(17) 0.0319(5) Uani 1 1 d . . . C17 C 0.4362(2) 0.63556(13) 0.2617(2) 0.0426(6) Uani 1 1 d . . . H17 H 0.4536 0.6781 0.2202 0.051 Uiso 1 1 calc R . . C18 C 0.4811(2) 0.56454(12) 0.24161(18) 0.0343(5) Uani 1 1 d . . . O4 O 0.2361(2) 0.26522(12) 0.41039(18) 0.0717(6) Uani 1 1 d D . . C1 C 0.3507(2) 0.18373(12) 0.79047(17) 0.0328(5) Uani 1 1 d . . . C16 C 0.3649(2) 0.64296(14) 0.3443(2) 0.0459(6) Uani 1 1 d . . . H16 H 0.3359 0.6913 0.3574 0.055 Uiso 1 1 calc R . . C14 C 0.5121(2) 0.08704(14) 0.87334(19) 0.0450(6) Uani 1 1 d . . . H14A H 0.5982 0.0932 0.8851 0.054 Uiso 1 1 calc R . . H14B H 0.4880 0.0990 0.9465 0.054 Uiso 1 1 calc R . . O3 O 0.3054(2) 0.36456(12) 0.5207(2) 0.0838(7) Uani 1 1 d . . . C3 C 0.3428(2) 0.23903(12) 0.60050(19) 0.0365(5) Uani 1 1 d . . . C25 C 0.6432(3) 0.59844(16) -0.0054(2) 0.0535(7) Uani 1 1 d . . . H25 H 0.6442 0.6351 -0.0629 0.064 Uiso 1 1 calc R . . C12 C 0.4912(2) 0.20208(14) 0.47371(19) 0.0445(6) Uani 1 1 d . . . H12A H 0.5773 0.1953 0.4918 0.053 Uiso 1 1 calc R . . H12B H 0.4745 0.2525 0.4395 0.053 Uiso 1 1 calc R . . C8 C 0.2921(2) 0.29658(17) 0.5064(2) 0.0534(7) Uani 1 1 d D . . C24 C 0.5655(2) 0.60758(15) 0.0700(2) 0.0516(7) Uani 1 1 d . . . H24 H 0.5143 0.6496 0.0618 0.062 Uiso 1 1 calc R . . C10 C 0.1866(2) 0.27934(16) 0.7166(2) 0.0533(7) Uani 1 1 d . . . H10A H 0.1894 0.2891 0.7989 0.064 Uiso 1 1 calc R . . H10B H 0.1882 0.3284 0.6780 0.064 Uiso 1 1 calc R . . C22 C 0.6401(2) 0.49394(15) 0.1634(2) 0.0543(7) Uani 1 1 d . . . H22 H 0.6417 0.4564 0.2202 0.065 Uiso 1 1 calc R . . C13 C 0.4359(3) 0.14161(16) 0.3850(2) 0.0623(8) Uani 1 1 d . . . H13A H 0.4684 0.1467 0.3155 0.093 Uiso 1 1 calc R . . H13B H 0.3507 0.1486 0.3659 0.093 Uiso 1 1 calc R . . H13C H 0.4538 0.0915 0.4177 0.093 Uiso 1 1 calc R . . C21 C 0.7152(3) 0.48865(16) 0.0850(2) 0.0574(7) Uani 1 1 d . . . H21 H 0.7676 0.4474 0.0911 0.069 Uiso 1 1 calc R . . C20 C 0.3761(3) 0.51613(16) 0.3838(3) 0.0663(9) Uani 1 1 d . . . H20 H 0.3552 0.4744 0.4250 0.080 Uiso 1 1 calc R . . C19 C 0.4472(3) 0.50398(15) 0.3032(2) 0.0598(8) Uani 1 1 d . . . H19 H 0.4724 0.4547 0.2902 0.072 Uiso 1 1 calc R . . C15 C 0.4805(3) 0.00504(15) 0.8416(3) 0.0702(9) Uani 1 1 d . . . H15A H 0.5201 -0.0280 0.9029 0.105 Uiso 1 1 calc R . . H15B H 0.5057 -0.0075 0.7701 0.105 Uiso 1 1 calc R . . H15C H 0.3955 -0.0017 0.8314 0.105 Uiso 1 1 calc R . . C11 C 0.0743(3) 0.2404(3) 0.6675(4) 0.1196(18) Uani 1 1 d . . . H11A H 0.0081 0.2718 0.6777 0.179 Uiso 1 1 calc R . . H11B H 0.0710 0.1924 0.7068 0.179 Uiso 1 1 calc R . . H11C H 0.0702 0.2313 0.5857 0.179 Uiso 1 1 calc R . . H2 H 0.224(3) 0.102(2) 0.9696(18) 0.104(12) Uiso 1 1 d D . . H6 H 0.667(3) 0.048(3) 0.569(5) 0.053(16) Uiso 0.50 1 d PD . . H4 H 0.215(6) 0.2991(15) 0.357(2) 0.26(4) Uiso 1 1 d D . . H2A H 0.771(3) 0.545(3) -0.045(3) 0.034(12) Uiso 0.50 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 O5 0.0403(10) 0.0730(13) 0.0438(10) -0.0165(9) 0.0102(8) 0.0020(9) O6 0.0500(11) 0.0455(10) 0.0551(11) -0.0128(8) 0.0302(9) -0.0029(8) C5 0.0366(13) 0.0323(11) 0.0271(10) -0.0021(9) 0.0119(9) -0.0043(9) C7 0.0430(14) 0.0412(13) 0.0334(12) -0.0008(10) 0.0200(10) 0.0006(11) O2 0.0912(15) 0.0574(12) 0.0470(11) -0.0130(9) 0.0456(10) -0.0283(11) N2 0.0423(12) 0.0545(13) 0.0368(10) 0.0054(9) 0.0187(9) 0.0016(10) N1 0.0590(14) 0.0484(13) 0.0454(12) -0.0056(10) 0.0298(10) -0.0038(11) O1 0.0997(16) 0.0576(12) 0.0498(11) -0.0175(9) 0.0426(11) -0.0185(10) C4 0.0426(13) 0.0313(12) 0.0271(10) 0.0014(9) 0.0134(9) -0.0046(10) C2 0.0382(13) 0.0403(13) 0.0366(12) 0.0030(10) 0.0112(10) 0.0019(11) C23 0.0339(12) 0.0368(12) 0.0292(10) -0.0011(9) 0.0109(9) -0.0043(10) C9 0.0400(14) 0.0391(13) 0.0271(10) 0.0007(9) 0.0152(9) -0.0003(11) C6 0.0406(13) 0.0323(12) 0.0252(10) 0.0020(9) 0.0126(9) -0.0010(10) C17 0.0516(15) 0.0388(14) 0.0429(13) 0.0051(11) 0.0223(11) 0.0012(11) C18 0.0397(13) 0.0376(13) 0.0277(10) -0.0006(9) 0.0118(9) -0.0054(10) O4 0.0987(17) 0.0621(13) 0.0464(11) 0.0017(10) -0.0051(11) 0.0083(12) C1 0.0393(13) 0.0348(12) 0.0279(10) -0.0009(9) 0.0158(9) -0.0037(10) C16 0.0549(16) 0.0415(14) 0.0462(14) -0.0062(11) 0.0217(12) 0.0012(12) C14 0.0533(15) 0.0552(15) 0.0302(11) 0.0128(11) 0.0173(10) 0.0121(12) O3 0.1098(19) 0.0495(13) 0.0796(16) 0.0189(11) -0.0111(13) -0.0087(12) C3 0.0432(14) 0.0342(12) 0.0332(11) 0.0060(9) 0.0101(10) 0.0002(10) C25 0.0669(18) 0.0588(17) 0.0423(14) 0.0183(12) 0.0287(13) 0.0097(15) C12 0.0585(16) 0.0476(14) 0.0329(12) 0.0089(10) 0.0225(11) 0.0007(12) C8 0.0578(18) 0.0510(17) 0.0499(16) 0.0025(13) 0.0073(13) 0.0075(14) C24 0.0659(18) 0.0491(15) 0.0476(14) 0.0138(12) 0.0303(13) 0.0186(13) C10 0.0495(16) 0.0648(18) 0.0484(15) 0.0016(13) 0.0164(12) 0.0139(14) C22 0.0641(17) 0.0543(16) 0.0535(15) 0.0241(13) 0.0332(13) 0.0173(14) C13 0.095(2) 0.0614(18) 0.0359(13) -0.0057(13) 0.0252(14) -0.0028(16) C21 0.0642(17) 0.0581(17) 0.0581(16) 0.0174(14) 0.0323(13) 0.0224(14) C20 0.102(2) 0.0435(15) 0.0723(19) 0.0013(14) 0.0638(18) -0.0065(16) C19 0.093(2) 0.0348(14) 0.0671(17) 0.0030(13) 0.0523(16) 0.0026(14) C15 0.124(3) 0.0459(16) 0.0474(15) 0.0155(13) 0.0323(16) 0.0144(17) C11 0.054(2) 0.154(4) 0.143(4) -0.087(3) 0.002(2) 0.015(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 O5 C9 1.226(3) . ? O6 C9 1.279(3) . ? C5 C4 1.396(3) . ? C5 C6 1.409(3) . ? C5 C9 1.499(3) . ? C7 O1 1.200(3) . ? C7 O2 1.295(3) . ? C7 C1 1.519(3) . ? N2 C25 1.319(3) . ? N2 C21 1.320(3) . ? N1 C16 1.319(3) . ? N1 C20 1.324(3) . ? C4 C3 1.392(3) . ? C4 C12 1.520(3) . ? C2 C1 1.397(3) . ? C2 C3 1.417(3) . ? C2 C10 1.501(3) . ? C23 C22 1.376(3) . ? C23 C24 1.381(3) . ? C23 C18 1.489(3) . ? C6 C1 1.389(3) . ? C6 C14 1.511(3) . ? C17 C18 1.379(3) . ? C17 C16 1.384(3) . ? C18 C19 1.376(3) . ? O4 C8 1.297(3) . ? C14 C15 1.505(4) . ? O3 C8 1.204(3) . ? C3 C8 1.516(3) . ? C25 C24 1.376(3) . ? C12 C13 1.525(3) . ? C10 C11 1.462(4) . ? C22 C21 1.373(3) . ? C20 C19 1.374(3) . ? 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 C4 C5 C6 121.6(2) . . ? C4 C5 C9 118.13(18) . . ? C6 C5 C9 120.22(19) . . ? O1 C7 O2 124.0(2) . . ? O1 C7 C1 123.3(2) . . ? O2 C7 C1 112.74(19) . . ? C25 N2 C21 118.0(2) . . ? C16 N1 C20 117.5(2) . . ? C3 C4 C5 118.01(19) . . ? C3 C4 C12 121.44(19) . . ? C5 C4 C12 120.5(2) . . ? C1 C2 C3 117.4(2) . . ? C1 C2 C10 121.5(2) . . ? C3 C2 C10 121.1(2) . . ? C22 C23 C24 116.3(2) . . ? C22 C23 C18 122.3(2) . . ? C24 C23 C18 121.4(2) . . ? O5 C9 O6 124.5(2) . . ? O5 C9 C5 120.14(19) . . ? O6 C9 C5 115.34(19) . . ? C1 C6 C5 118.45(19) . . ? C1 C6 C14 122.47(18) . . ? C5 C6 C14 119.03(19) . . ? C18 C17 C16 119.4(2) . . ? C19 C18 C17 116.7(2) . . ? C19 C18 C23 122.3(2) . . ? C17 C18 C23 121.0(2) . . ? C6 C1 C2 122.16(19) . . ? C6 C1 C7 118.31(19) . . ? C2 C1 C7 119.52(19) . . ? N1 C16 C17 123.2(2) . . ? C15 C14 C6 112.7(2) . . ? C4 C3 C2 122.2(2) . . ? C4 C3 C8 117.5(2) . . ? C2 C3 C8 120.0(2) . . ? N2 C25 C24 122.2(2) . . ? C4 C12 C13 112.2(2) . . ? O3 C8 O4 124.3(3) . . ? O3 C8 C3 122.2(2) . . ? O4 C8 C3 113.5(2) . . ? C25 C24 C23 120.5(2) . . ? C11 C10 C2 113.1(2) . . ? C21 C22 C23 119.8(2) . . ? N2 C21 C22 123.1(2) . . ? N1 C20 C19 122.8(2) . . ? C20 C19 C18 120.2(2) . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.794 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.051