# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Tanaka, Koichi' 'Asami, Masaya' 'Scott, Janet L.' _publ_contact_author_name 'Prof Koichi Tanaka' _publ_contact_author_address ; Applied Chemistry Ehime University Department of Applied Chemistry, Fa Matsuyama Ehime 790-8577 JAPAN ; _publ_contact_author_email 'TANAKA@EN3.EHIME-U.AC.JP' _publ_section_title ; A novel chromogenic host compound which shows sensitive color change upon inclusion crystallization ; data_compound_1 _database_code_CSD 174130 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{4-[4-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl}-1,1-diphenyl- prop-2-yn-1-ol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H30 N2 O2' _chemical_formula_sum 'C42 H0 N2 O2' _chemical_formula_weight 594.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7388(2) _cell_length_b 8.7259(3) _cell_length_c 14.5005(6) _cell_angle_alpha 103.6430(10) _cell_angle_beta 94.729(2) _cell_angle_gamma 106.122(2) _cell_volume 785.96(5) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _exptl_crystal_description 'thin elongated plates' _exptl_crystal_colour 'dichroic yellow / amber' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details ? _exptl_special_details ; All non-hydrogen atoms were refined anisotropically. Hydrogen atoms, except that of the OH group, were inserted at geometrically determined positions with temperature factors fixed at 1.2 times that of the parent atom. The hydrogen bonded hydroxyl hydrogen atom was located in electron density difference maps and refined. ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 7755 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0851 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3796 _reflns_number_gt 2293 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0661P)^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 3796 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 N1 N -0.0052(2) 0.07093(16) -0.00150(10) 0.0237(3) Uani 1 1 d . . . O1 O 1.22368(17) 0.85341(13) 0.16769(8) 0.0264(3) Uani 1 1 d . . . C4 C 0.5359(2) 0.4760(2) 0.11906(12) 0.0248(4) Uani 1 1 d . . . C6 C 0.1645(3) 0.3615(2) 0.06445(12) 0.0250(4) Uani 1 1 d . . . H6 H 0.0316 0.3773 0.0533 0.030 Uiso 1 1 calc R . . C2 C 0.3785(2) 0.1802(2) 0.05258(12) 0.0270(4) Uani 1 1 d . . . H2 H 0.3917 0.0719 0.0347 0.032 Uiso 1 1 calc R . . C1 C 0.1825(2) 0.20254(19) 0.04017(11) 0.0221(4) Uani 1 1 d . . . C5 C 0.3393(3) 0.4968(2) 0.10474(12) 0.0261(4) Uani 1 1 d . . . H5 H 0.3251 0.6047 0.1228 0.031 Uiso 1 1 calc R . . C9 C 1.0773(2) 0.86209(19) 0.23384(12) 0.0235(4) Uani 1 1 d . . . C7 C 0.7212(3) 0.6148(2) 0.15960(12) 0.0271(4) Uani 1 1 d . . . C10 C 1.1654(2) 0.83163(19) 0.32642(12) 0.0238(4) Uani 1 1 d . . . C3 C 0.5535(3) 0.3151(2) 0.09075(13) 0.0280(4) Uani 1 1 d . . . H3 H 0.6873 0.2995 0.0980 0.034 Uiso 1 1 calc R . . C21 C 1.2285(3) 1.1703(2) 0.29201(13) 0.0298(4) Uani 1 1 d . . . H21 H 1.3604 1.1522 0.3018 0.036 Uiso 1 1 calc R . . C20 C 1.0490(2) 1.0352(2) 0.25574(12) 0.0237(4) Uani 1 1 d . . . C11 C 1.0457(3) 0.8303(2) 0.40006(13) 0.0300(4) Uani 1 1 d . . . H11 H 0.9147 0.8507 0.3924 0.036 Uiso 1 1 calc R . . C15 C 1.3578(3) 0.8055(2) 0.33875(13) 0.0280(4) Uani 1 1 d . . . H15 H 1.4418 0.8076 0.2893 0.034 Uiso 1 1 calc R . . C25 C 0.8571(3) 1.0625(2) 0.24236(13) 0.0296(4) Uani 1 1 d . . . H25 H 0.7332 0.9718 0.2173 0.035 Uiso 1 1 calc R . . C13 C 1.3066(3) 0.7714(2) 0.49602(13) 0.0338(4) Uani 1 1 d . . . H13 H 1.3543 0.7489 0.5534 0.041 Uiso 1 1 calc R . . C24 C 0.8475(3) 1.2251(2) 0.26614(13) 0.0361(5) Uani 1 1 d . . . H24 H 0.7159 1.2441 0.2577 0.043 Uiso 1 1 calc R . . C23 C 1.0256(3) 1.3576(2) 0.30152(14) 0.0386(5) Uani 1 1 d . . . H23 H 1.0169 1.4674 0.3173 0.046 Uiso 1 1 calc R . . C12 C 1.1150(3) 0.7997(2) 0.48449(13) 0.0352(5) Uani 1 1 d . . . H12 H 1.0316 0.7981 0.5342 0.042 Uiso 1 1 calc R . . C8 C 0.8763(3) 0.7280(2) 0.19221(12) 0.0273(4) Uani 1 1 d . . . C14 C 1.4280(3) 0.7760(2) 0.42432(13) 0.0336(4) Uani 1 1 d . . . H14 H 1.5607 0.7590 0.4331 0.040 Uiso 1 1 calc R . . C22 C 1.2170(3) 1.3305(2) 0.31393(14) 0.0369(5) Uani 1 1 d . . . H22 H 1.3409 1.4217 0.3375 0.044 Uiso 1 1 calc R . . H1O H 1.1846 0.8932 0.1162 0.071(7) Uiso 1 1 d 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 N1 0.0244(7) 0.0203(7) 0.0243(8) 0.0065(6) 0.0040(6) 0.0034(6) O1 0.0285(6) 0.0244(6) 0.0265(7) 0.0074(5) 0.0065(5) 0.0073(5) C4 0.0259(9) 0.0224(9) 0.0213(9) 0.0063(7) 0.0011(7) 0.0000(7) C6 0.0221(8) 0.0244(9) 0.0280(9) 0.0074(8) 0.0028(7) 0.0064(7) C2 0.0269(9) 0.0198(9) 0.0346(10) 0.0079(8) 0.0072(8) 0.0068(7) C1 0.0228(8) 0.0198(8) 0.0213(9) 0.0062(7) 0.0028(7) 0.0023(7) C5 0.0308(9) 0.0199(9) 0.0257(10) 0.0053(7) 0.0055(7) 0.0054(8) C9 0.0210(8) 0.0207(9) 0.0254(9) 0.0053(7) 0.0025(7) 0.0022(7) C7 0.0298(9) 0.0229(9) 0.0269(10) 0.0087(8) 0.0056(7) 0.0031(8) C10 0.0257(9) 0.0155(8) 0.0254(9) 0.0029(7) 0.0012(7) 0.0016(7) C3 0.0239(9) 0.0280(10) 0.0315(10) 0.0097(8) 0.0034(7) 0.0058(8) C21 0.0282(9) 0.0231(9) 0.0368(11) 0.0078(8) 0.0043(8) 0.0062(8) C20 0.0256(9) 0.0237(9) 0.0224(9) 0.0084(7) 0.0041(7) 0.0064(7) C11 0.0302(9) 0.0285(10) 0.0325(10) 0.0094(8) 0.0055(8) 0.0099(8) C15 0.0272(9) 0.0240(9) 0.0296(10) 0.0073(8) 0.0029(7) 0.0033(7) C25 0.0303(9) 0.0331(10) 0.0287(10) 0.0146(8) 0.0058(8) 0.0095(8) C13 0.0412(11) 0.0297(10) 0.0282(10) 0.0105(8) -0.0020(8) 0.0071(9) C24 0.0418(11) 0.0449(12) 0.0378(11) 0.0233(9) 0.0168(9) 0.0259(10) C23 0.0598(13) 0.0282(10) 0.0369(11) 0.0141(9) 0.0172(10) 0.0207(10) C12 0.0441(11) 0.0346(11) 0.0283(10) 0.0107(9) 0.0090(9) 0.0116(9) C8 0.0312(10) 0.0246(9) 0.0258(10) 0.0083(8) 0.0042(8) 0.0071(8) C14 0.0286(9) 0.0305(10) 0.0385(11) 0.0096(9) -0.0026(8) 0.0060(8) C22 0.0444(11) 0.0238(10) 0.0387(11) 0.0068(9) 0.0071(9) 0.0059(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N1 1.270(2) 2 ? N1 C1 1.423(2) . ? O1 C9 1.4358(19) . ? C4 C5 1.392(2) . ? C4 C3 1.408(2) . ? C4 C7 1.440(2) . ? C6 C5 1.382(2) . ? C6 C1 1.391(2) . ? C2 C3 1.377(2) . ? C2 C1 1.391(2) . ? C9 C8 1.490(2) . ? C9 C10 1.533(2) . ? C9 C20 1.538(2) . ? C7 C8 1.191(2) . ? C10 C15 1.382(2) . ? C10 C11 1.391(2) . ? C21 C22 1.384(2) . ? C21 C20 1.393(2) . ? C20 C25 1.385(2) . ? C11 C12 1.385(2) . ? C15 C14 1.397(2) . ? C25 C24 1.400(2) . ? C13 C14 1.376(3) . ? C13 C12 1.385(2) . ? C24 C23 1.374(3) . ? C23 C22 1.380(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 N1 N1 C1 114.09(17) 2 . ? C5 C4 C3 118.74(15) . . ? C5 C4 C7 121.75(15) . . ? C3 C4 C7 119.49(15) . . ? C5 C6 C1 120.27(15) . . ? C3 C2 C1 119.96(15) . . ? C6 C1 C2 119.82(15) . . ? C6 C1 N1 116.43(14) . . ? C2 C1 N1 123.67(14) . . ? C6 C5 C4 120.51(15) . . ? O1 C9 C8 109.39(13) . . ? O1 C9 C10 108.42(12) . . ? C8 C9 C10 107.81(13) . . ? O1 C9 C20 109.00(12) . . ? C8 C9 C20 112.19(13) . . ? C10 C9 C20 109.96(13) . . ? C8 C7 C4 178.85(19) . . ? C15 C10 C11 119.41(16) . . ? C15 C10 C9 122.37(15) . . ? C11 C10 C9 118.22(14) . . ? C2 C3 C4 120.63(15) . . ? C22 C21 C20 120.80(16) . . ? C25 C20 C21 119.27(15) . . ? C25 C20 C9 123.72(15) . . ? C21 C20 C9 117.00(14) . . ? C12 C11 C10 120.79(16) . . ? C10 C15 C14 119.64(16) . . ? C20 C25 C24 119.31(17) . . ? C14 C13 C12 119.96(17) . . ? C23 C24 C25 120.98(17) . . ? C24 C23 C22 119.68(16) . . ? C13 C12 C11 119.60(17) . . ? C7 C8 C9 176.41(17) . . ? C13 C14 C15 120.58(16) . . ? C23 C22 C21 119.94(18) . . ? 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 C6 C1 C2 -2.8(2) . . . . ? C5 C6 C1 N1 -179.59(15) . . . . ? C3 C2 C1 C6 1.4(2) . . . . ? C3 C2 C1 N1 177.90(15) . . . . ? N1 N1 C1 C6 -161.86(16) 2 . . . ? N1 N1 C1 C2 21.5(3) 2 . . . ? C1 C6 C5 C4 1.8(2) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C7 C4 C5 C6 179.09(16) . . . . ? C5 C4 C7 C8 -150(10) . . . . ? C3 C4 C7 C8 28(10) . . . . ? O1 C9 C10 C15 1.5(2) . . . . ? C8 C9 C10 C15 119.83(16) . . . . ? C20 C9 C10 C15 -117.57(16) . . . . ? O1 C9 C10 C11 -178.40(14) . . . . ? C8 C9 C10 C11 -60.08(18) . . . . ? C20 C9 C10 C11 62.52(18) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C5 C4 C3 C2 -2.2(2) . . . . ? C7 C4 C3 C2 179.42(16) . . . . ? C22 C21 C20 C25 -0.5(3) . . . . ? C22 C21 C20 C9 -179.83(15) . . . . ? O1 C9 C20 C25 124.09(16) . . . . ? C8 C9 C20 C25 2.8(2) . . . . ? C10 C9 C20 C25 -117.19(17) . . . . ? O1 C9 C20 C21 -56.63(19) . . . . ? C8 C9 C20 C21 -177.93(15) . . . . ? C10 C9 C20 C21 62.10(18) . . . . ? C15 C10 C11 C12 -1.4(2) . . . . ? C9 C10 C11 C12 178.52(15) . . . . ? C11 C10 C15 C14 0.9(2) . . . . ? C9 C10 C15 C14 -179.06(15) . . . . ? C21 C20 C25 C24 -0.4(2) . . . . ? C9 C20 C25 C24 178.87(15) . . . . ? C20 C25 C24 C23 0.7(3) . . . . ? C25 C24 C23 C22 0.0(3) . . . . ? C14 C13 C12 C11 0.8(3) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C4 C7 C8 C9 -43(12) . . . . ? O1 C9 C8 C7 69(3) . . . . ? C10 C9 C8 C7 -48(3) . . . . ? C20 C9 C8 C7 -170(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C10 C15 C14 C13 0.5(3) . . . . ? C24 C23 C22 C21 -0.9(3) . . . . ? C20 C21 C22 C23 1.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.208 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.055 #===END data_compound_2 _database_code_CSD 174131 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-{4-[4-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl}-1,1-diphenyl- prop-2-yn-1-ol DMF solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H30 O2 . 2(C3 H7 N O)' _chemical_formula_sum 'C48 H44 N4 O4' _chemical_formula_weight 740.87 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 8.83450(10) _cell_length_b 12.12230(10) _cell_length_c 19.11560(10) _cell_angle_alpha 102.6980(10) _cell_angle_beta 93.4710(10) _cell_angle_gamma 97.4730(10) _cell_volume 1971.72(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _exptl_crystal_description 'tabular crystals' _exptl_crystal_colour 'dichroic red / orange' _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_special_details ; All non-hydrogen atoms of the host (1) were refined anisotropically. Hydrogen atoms, except that of the OH group, were inserted at geometrically determined positions with temperature factors fixed at 1.2 times that of the parent atom except for methyl hydrogens which were modeled at 1.5 times that of the parent atom. The hydrogen bonded hydroxyl hydrogen atom was located in electron density difference maps and refined. One of the DMF guest molecules exhibits disorder of the carbonyl group. Three positions were modeled for the guest carbonyl oxygen atom: two minor positions (20% site occupancy) and a primary position (60% site occupancy). ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 19898 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.35 _reflns_number_total 9498 _reflns_number_gt 6076 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement '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^)+(0.0453P)^2^+0.7368P] 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 9498 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 O1' O 0.06525(15) 0.97013(11) 0.11830(7) 0.0245(3) Uani 1 1 d . . . O1 O -0.46478(16) 1.55674(12) 0.75434(7) 0.0263(3) Uani 1 1 d . . . N1 N -0.01027(17) 1.03705(13) 0.48232(9) 0.0234(3) Uani 1 1 d . . . N1' N -0.51289(18) 1.02153(14) 0.47356(8) 0.0257(4) Uani 1 1 d . . . C8 C -0.4138(2) 1.45636(16) 0.63855(10) 0.0237(4) Uani 1 1 d . . . C7 C -0.3490(2) 1.38188(16) 0.60745(10) 0.0239(4) Uani 1 1 d . . . C9 C -0.4767(2) 1.55670(15) 0.67961(10) 0.0209(4) Uani 1 1 d . . . C20' C -0.0986(2) 0.79133(15) 0.05957(10) 0.0211(4) Uani 1 1 d . . . C10' C 0.1479(2) 0.80206(15) 0.13866(10) 0.0217(4) Uani 1 1 d . . . C7' C -0.1620(2) 0.88972(16) 0.23959(10) 0.0236(4) Uani 1 1 d . . . C4' C -0.2566(2) 0.91717(16) 0.29811(10) 0.0233(4) Uani 1 1 d . . . C1 C -0.0925(2) 1.12363(15) 0.51745(10) 0.0211(4) Uani 1 1 d . . . C9' C 0.0056(2) 0.85876(15) 0.12637(10) 0.0206(4) Uani 1 1 d . . . C20 C -0.6447(2) 1.55703(16) 0.65346(10) 0.0217(4) Uani 1 1 d . . . C3 C -0.2317(2) 1.27684(16) 0.50340(10) 0.0242(4) Uani 1 1 d . . . H3 H -0.2696 1.3227 0.4739 0.029 Uiso 1 1 calc R . . C5 C -0.2062(2) 1.22570(16) 0.61811(11) 0.0274(4) Uani 1 1 d . . . H5 H -0.2256 1.2379 0.6674 0.033 Uiso 1 1 calc R . . C2' C -0.3629(2) 0.87950(17) 0.40562(10) 0.0254(4) Uani 1 1 d . . . H2' H -0.3753 0.8333 0.4397 0.031 Uiso 1 1 calc R . . C6 C -0.1218(2) 1.14131(16) 0.58950(11) 0.0279(4) Uani 1 1 d . . . H6 H -0.0837 1.0954 0.6189 0.033 Uiso 1 1 calc R . . C10 C -0.3737(2) 1.66367(15) 0.67037(10) 0.0214(4) Uani 1 1 d . . . C8' C -0.0845(2) 0.87130(16) 0.19044(10) 0.0235(4) Uani 1 1 d . . . C4 C -0.2637(2) 1.29362(15) 0.57517(10) 0.0224(4) Uani 1 1 d . . . C21' C -0.0780(2) 0.81818(17) -0.00685(10) 0.0283(4) Uani 1 1 d . . . H21' H -0.0044 0.8812 -0.0097 0.034 Uiso 1 1 calc R . . C3' C -0.2775(2) 0.84886(17) 0.34795(10) 0.0259(4) Uani 1 1 d . . . H3' H -0.2326 0.7807 0.3422 0.031 Uiso 1 1 calc R . . C14 C -0.2006(2) 1.83757(17) 0.72015(12) 0.0346(5) Uani 1 1 d . . . H14 H -0.1499 1.8922 0.7610 0.042 Uiso 1 1 calc R . . C1' C -0.4308(2) 0.97907(16) 0.41344(10) 0.0242(4) Uani 1 1 d . . . C11' C 0.2349(2) 0.83540(17) 0.20451(10) 0.0255(4) Uani 1 1 d . . . H11' H 0.2008 0.8879 0.2428 0.031 Uiso 1 1 calc R . . C2 C -0.1447(2) 1.19336(15) 0.47508(10) 0.0232(4) Uani 1 1 d . . . H2 H -0.1205 1.1836 0.4266 0.028 Uiso 1 1 calc R . . C15 C -0.2994(2) 1.74410(16) 0.72953(11) 0.0280(4) Uani 1 1 d . . . H15 H -0.3161 1.7353 0.7767 0.034 Uiso 1 1 calc R . . C6' C -0.4187(2) 1.04345(17) 0.36210(10) 0.0277(4) Uani 1 1 d . . . H6' H -0.4709 1.1079 0.3658 0.033 Uiso 1 1 calc R . . C11 C -0.3502(2) 1.67950(17) 0.60136(11) 0.0270(4) Uani 1 1 d . . . H11 H -0.4021 1.6260 0.5603 0.032 Uiso 1 1 calc R . . C5' C -0.3301(2) 1.01389(17) 0.30522(10) 0.0273(4) Uani 1 1 d . . . H5' H -0.3195 1.0597 0.2709 0.033 Uiso 1 1 calc R . . C25' C -0.2077(2) 0.69986(16) 0.06308(11) 0.0281(4) Uani 1 1 d . . . H25' H -0.2241 0.6814 0.1081 0.034 Uiso 1 1 calc R . . C12 C -0.2520(2) 1.77248(17) 0.59272(12) 0.0313(5) Uani 1 1 d . . . H12 H -0.2364 1.7825 0.5456 0.038 Uiso 1 1 calc R . . C15' C 0.1996(2) 0.72569(17) 0.08324(11) 0.0299(5) Uani 1 1 d . . . H15' H 0.1411 0.7012 0.0378 0.036 Uiso 1 1 calc R . . C13 C -0.1754(2) 1.85175(17) 0.65203(12) 0.0323(5) Uani 1 1 d . . . H13 H -0.1065 1.9151 0.6457 0.039 Uiso 1 1 calc R . . C21 C -0.7184(2) 1.64626(17) 0.68782(11) 0.0299(5) Uani 1 1 d . . . H21 H -0.6628 1.7068 0.7242 0.036 Uiso 1 1 calc R . . C25 C -0.7265(2) 1.47033(17) 0.60002(11) 0.0281(4) Uani 1 1 d . . . H25 H -0.6772 1.4096 0.5760 0.034 Uiso 1 1 calc R . . C23' C -0.2708(2) 0.66161(19) -0.06513(12) 0.0367(5) Uani 1 1 d . . . H23' H -0.3285 0.6167 -0.1077 0.044 Uiso 1 1 calc R . . C12' C 0.3710(2) 0.79355(18) 0.21553(12) 0.0308(5) Uani 1 1 d . . . H12' H 0.4284 0.8165 0.2613 0.037 Uiso 1 1 calc R . . C13' C 0.4233(2) 0.71815(18) 0.15981(12) 0.0336(5) Uani 1 1 d . . . H13' H 0.5171 0.6900 0.1669 0.040 Uiso 1 1 calc R . . C22' C -0.1640(2) 0.75367(19) -0.06847(11) 0.0349(5) Uani 1 1 d . . . H22' H -0.1496 0.7728 -0.1134 0.042 Uiso 1 1 calc R . . C14' C 0.3377(2) 0.68475(19) 0.09433(12) 0.0365(5) Uani 1 1 d . . . H14' H 0.3729 0.6331 0.0560 0.044 Uiso 1 1 calc R . . C24' C -0.2934(2) 0.63518(19) 0.00042(12) 0.0356(5) Uani 1 1 d . . . H24' H -0.3678 0.5724 0.0029 0.043 Uiso 1 1 calc R . . C24 C -0.8814(2) 1.4717(2) 0.58121(13) 0.0379(5) Uani 1 1 d . . . H24 H -0.9370 1.4120 0.5444 0.046 Uiso 1 1 calc R . . C22 C -0.8723(2) 1.6469(2) 0.66911(13) 0.0371(5) Uani 1 1 d . . . H22 H -0.9221 1.7076 0.6929 0.044 Uiso 1 1 calc R . . C23 C -0.9537(2) 1.5594(2) 0.61589(13) 0.0414(6) Uani 1 1 d . . . H23 H -1.0593 1.5598 0.6033 0.050 Uiso 1 1 calc R . . H1O H -0.541(3) 1.507(2) 0.7640(13) 0.045(7) Uiso 1 1 d . . . H1'O H -0.017(3) 1.008(2) 0.1150(14) 0.057(8) Uiso 1 1 d . . . O1B O 0.82496(16) 0.08435(13) 0.10873(10) 0.0453(4) Uani 1 1 d . . . N1B N 0.56756(19) 0.08052(16) 0.09658(11) 0.0392(5) Uani 1 1 d . . . C1B C 0.6935(2) 0.03662(19) 0.10877(12) 0.0351(5) Uani 1 1 d . . . H1B H 0.6813 -0.0376 0.1183 0.042 Uiso 1 1 calc R . . C2B C 0.4150(2) 0.0223(2) 0.10123(14) 0.0446(6) Uani 1 1 d . . . H2B1 H 0.4223 -0.0544 0.1085 0.067 Uiso 1 1 calc R . . H2B2 H 0.3509 0.0162 0.0565 0.067 Uiso 1 1 calc R . . H2B3 H 0.3689 0.0659 0.1418 0.067 Uiso 1 1 calc R . . C3B C 0.5783(3) 0.1932(2) 0.0809(2) 0.0695(10) Uani 1 1 d . . . H3B1 H 0.5588 0.2489 0.1238 0.104 Uiso 1 1 calc R . . H3B2 H 0.5021 0.1915 0.0411 0.104 Uiso 1 1 calc R . . H3B3 H 0.6812 0.2151 0.0674 0.104 Uiso 1 1 calc R . . C1A C -0.8455(3) 1.4311(2) 0.77179(14) 0.0430(6) Uani 1 1 d . A 1 H1A H -0.8814 1.3921 0.7237 0.052 Uiso 1 1 calc R A 1 C2A C -1.0983(2) 1.4853(2) 0.78188(12) 0.0362(5) Uani 1 1 d . A 1 H2A1 H -1.1147 1.4400 0.7321 0.054 Uiso 1 1 calc R A 1 H2A2 H -1.1144 1.5641 0.7829 0.054 Uiso 1 1 calc R A 1 H2A3 H -1.1710 1.4521 0.8111 0.054 Uiso 1 1 calc R A 1 C3A C -0.8998(4) 1.5491(2) 0.88462(17) 0.0740(10) Uani 1 1 d . A 1 H3A1 H -0.9674 1.5183 0.9168 0.111 Uiso 1 1 calc R A 1 H3A2 H -0.9097 1.6297 0.8882 0.111 Uiso 1 1 calc R A 1 H3A3 H -0.7934 1.5426 0.8986 0.111 Uiso 1 1 calc R A 1 N1A N -0.94292(19) 1.48481(14) 0.81081(10) 0.0327(4) Uani 1 1 d . A 1 O1A O -0.7119(4) 1.4269(3) 0.7921(2) 0.0283(9) Uiso 0.60 1 d P A 1 O1AB O -0.6937(8) 1.4601(7) 0.8127(4) 0.0203(19) Uiso 0.20 1 d P B 2 O1AA O -0.7217(9) 1.3983(7) 0.7704(4) 0.021(2) Uiso 0.20 1 d P C 3 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' 0.0199(7) 0.0243(7) 0.0304(8) 0.0075(6) 0.0041(5) 0.0046(6) O1 0.0279(7) 0.0309(8) 0.0214(7) 0.0090(6) 0.0022(6) 0.0043(6) N1 0.0209(8) 0.0220(8) 0.0289(9) 0.0068(7) 0.0043(7) 0.0063(7) N1' 0.0221(8) 0.0322(9) 0.0216(9) 0.0032(7) 0.0060(7) 0.0033(7) C8 0.0196(9) 0.0239(10) 0.0282(11) 0.0079(8) 0.0009(8) 0.0028(8) C7 0.0216(9) 0.0211(10) 0.0295(11) 0.0067(8) 0.0033(8) 0.0031(8) C9 0.0205(9) 0.0225(9) 0.0206(10) 0.0051(8) 0.0014(7) 0.0063(8) C20' 0.0176(9) 0.0248(10) 0.0216(10) 0.0041(8) 0.0036(7) 0.0074(8) C10' 0.0177(9) 0.0242(10) 0.0244(10) 0.0071(8) 0.0053(7) 0.0036(8) C7' 0.0204(9) 0.0286(10) 0.0211(10) 0.0038(8) 0.0015(8) 0.0050(8) C4' 0.0175(9) 0.0300(10) 0.0200(10) 0.0015(8) 0.0024(7) 0.0015(8) C1 0.0180(9) 0.0200(9) 0.0255(10) 0.0045(8) 0.0039(7) 0.0039(7) C9' 0.0192(9) 0.0234(9) 0.0204(10) 0.0054(8) 0.0055(7) 0.0054(8) C20 0.0178(9) 0.0254(10) 0.0249(10) 0.0104(8) 0.0041(7) 0.0051(8) C3 0.0214(9) 0.0240(10) 0.0284(11) 0.0075(8) 0.0008(8) 0.0065(8) C5 0.0320(11) 0.0264(10) 0.0266(11) 0.0077(8) 0.0084(8) 0.0091(9) C2' 0.0238(10) 0.0309(11) 0.0222(10) 0.0067(8) 0.0039(8) 0.0043(8) C6 0.0332(11) 0.0251(10) 0.0298(11) 0.0099(8) 0.0067(9) 0.0122(9) C10 0.0192(9) 0.0209(9) 0.0258(10) 0.0056(8) 0.0030(7) 0.0081(8) C8' 0.0197(9) 0.0281(10) 0.0232(10) 0.0067(8) 0.0012(8) 0.0046(8) C4 0.0174(9) 0.0198(9) 0.0297(11) 0.0036(8) 0.0041(8) 0.0039(7) C21' 0.0279(10) 0.0323(11) 0.0261(11) 0.0075(9) 0.0030(8) 0.0083(9) C3' 0.0216(9) 0.0336(11) 0.0231(10) 0.0039(8) 0.0043(8) 0.0094(8) C14 0.0344(11) 0.0259(11) 0.0396(13) 0.0022(9) 0.0000(10) 0.0009(9) C1' 0.0177(9) 0.0318(11) 0.0210(10) 0.0015(8) 0.0035(7) 0.0031(8) C11' 0.0220(9) 0.0308(11) 0.0247(10) 0.0076(8) 0.0040(8) 0.0048(8) C2 0.0222(9) 0.0242(10) 0.0235(10) 0.0061(8) 0.0022(8) 0.0039(8) C15 0.0295(10) 0.0268(10) 0.0266(11) 0.0042(8) 0.0015(8) 0.0045(9) C6' 0.0278(10) 0.0305(11) 0.0247(11) 0.0026(9) 0.0061(8) 0.0089(9) C11 0.0268(10) 0.0284(10) 0.0257(11) 0.0055(8) 0.0015(8) 0.0051(9) C5' 0.0291(10) 0.0310(11) 0.0229(10) 0.0067(8) 0.0070(8) 0.0058(9) C25' 0.0238(10) 0.0296(11) 0.0301(11) 0.0046(9) 0.0063(8) 0.0040(9) C12 0.0316(11) 0.0347(12) 0.0329(12) 0.0151(10) 0.0097(9) 0.0079(9) C15' 0.0245(10) 0.0349(11) 0.0292(11) 0.0025(9) 0.0019(8) 0.0094(9) C13 0.0265(10) 0.0250(11) 0.0481(14) 0.0125(10) 0.0094(9) 0.0041(9) C21 0.0279(10) 0.0307(11) 0.0345(12) 0.0102(9) 0.0065(9) 0.0103(9) C25 0.0245(10) 0.0324(11) 0.0286(11) 0.0102(9) 0.0032(8) 0.0033(9) C23' 0.0298(11) 0.0449(13) 0.0303(12) -0.0063(10) -0.0066(9) 0.0164(10) C12' 0.0209(10) 0.0418(12) 0.0323(12) 0.0155(10) 0.0000(8) 0.0030(9) C13' 0.0209(10) 0.0397(12) 0.0457(14) 0.0167(10) 0.0051(9) 0.0117(9) C22' 0.0387(12) 0.0445(13) 0.0222(11) 0.0059(9) -0.0023(9) 0.0140(11) C14' 0.0297(11) 0.0395(12) 0.0419(13) 0.0046(10) 0.0082(10) 0.0170(10) C24' 0.0227(10) 0.0331(12) 0.0457(14) -0.0021(10) 0.0033(9) 0.0034(9) C24 0.0255(11) 0.0488(14) 0.0396(13) 0.0175(11) -0.0058(9) -0.0027(10) C22 0.0301(11) 0.0450(13) 0.0485(14) 0.0258(11) 0.0152(10) 0.0201(10) C23 0.0194(10) 0.0597(16) 0.0546(15) 0.0328(13) 0.0030(10) 0.0075(11) O1B 0.0251(8) 0.0475(10) 0.0733(12) 0.0286(9) 0.0138(8) 0.0132(7) N1B 0.0244(9) 0.0448(11) 0.0608(13) 0.0310(10) 0.0159(9) 0.0131(8) C1B 0.0309(11) 0.0402(12) 0.0424(13) 0.0196(10) 0.0108(10) 0.0152(10) C2B 0.0262(11) 0.0571(15) 0.0556(16) 0.0219(13) 0.0105(11) 0.0064(11) C3B 0.0382(14) 0.0615(18) 0.135(3) 0.0631(19) 0.0316(17) 0.0247(13) C1A 0.0325(12) 0.0614(16) 0.0508(15) 0.0360(13) 0.0186(11) 0.0180(12) C2A 0.0234(10) 0.0443(13) 0.0399(13) 0.0077(10) 0.0019(9) 0.0056(10) C3A 0.0668(19) 0.0572(18) 0.081(2) -0.0209(16) -0.0344(17) 0.0272(15) N1A 0.0243(9) 0.0305(9) 0.0427(11) 0.0071(8) 0.0011(8) 0.0053(8) _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' C9' 1.429(2) . ? O1 C9 1.426(2) . ? N1 N1 1.262(3) 2_576 ? N1 C1 1.424(2) . ? N1' N1' 1.257(3) 2_476 ? N1' C1' 1.432(2) . ? C8 C7 1.198(3) . ? C8 C9 1.487(3) . ? C7 C4 1.439(2) . ? C9 C10 1.534(3) . ? C9 C20 1.539(2) . ? C20' C25' 1.388(3) . ? C20' C21' 1.395(3) . ? C20' C9' 1.532(3) . ? C10' C11' 1.385(3) . ? C10' C15' 1.388(3) . ? C10' C9' 1.539(2) . ? C7' C8' 1.194(3) . ? C7' C4' 1.443(3) . ? C4' C5' 1.398(3) . ? C4' C3' 1.398(3) . ? C1 C6 1.392(3) . ? C1 C2 1.393(2) . ? C9' C8' 1.491(2) . ? C20 C25 1.383(3) . ? C20 C21 1.395(3) . ? C3 C2 1.386(2) . ? C3 C4 1.394(3) . ? C5 C6 1.380(3) . ? C5 C4 1.402(3) . ? C2' C3' 1.384(3) . ? C2' C1' 1.400(3) . ? C10 C15 1.385(3) . ? C10 C11 1.398(3) . ? C21' C22' 1.382(3) . ? C14 C13 1.378(3) . ? C14 C15 1.389(3) . ? C1' C6' 1.383(3) . ? C11' C12' 1.386(3) . ? C6' C5' 1.388(3) . ? C11 C12 1.377(3) . ? C25' C24' 1.395(3) . ? C12 C13 1.388(3) . ? C15' C14' 1.398(3) . ? C21 C22 1.387(3) . ? C25 C24 1.396(3) . ? C23' C24' 1.379(3) . ? C23' C22' 1.380(3) . ? C12' C13' 1.387(3) . ? C13' C14' 1.373(3) . ? C24 C23 1.377(3) . ? C22 C23 1.384(3) . ? O1B C1B 1.228(3) . ? N1B C1B 1.324(3) . ? N1B C3B 1.454(3) . ? N1B C2B 1.456(3) . ? C1A O1A 1.230(4) . ? C1A N1A 1.316(3) . ? C2A N1A 1.450(3) . ? C3A N1A 1.455(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 N1 N1 C1 114.02(19) 2_576 . ? N1' N1' C1' 113.21(19) 2_476 . ? C7 C8 C9 173.5(2) . . ? C8 C7 C4 175.6(2) . . ? O1 C9 C8 109.50(14) . . ? O1 C9 C10 107.52(15) . . ? C8 C9 C10 106.75(14) . . ? O1 C9 C20 109.69(14) . . ? C8 C9 C20 112.04(15) . . ? C10 C9 C20 111.19(14) . . ? C25' C20' C21' 119.17(18) . . ? C25' C20' C9' 121.23(17) . . ? C21' C20' C9' 119.51(17) . . ? C11' C10' C15' 118.70(16) . . ? C11' C10' C9' 119.52(16) . . ? C15' C10' C9' 121.51(17) . . ? C8' C7' C4' 177.2(2) . . ? C5' C4' C3' 118.91(16) . . ? C5' C4' C7' 119.49(17) . . ? C3' C4' C7' 121.60(16) . . ? C6 C1 C2 119.89(16) . . ? C6 C1 N1 124.23(16) . . ? C2 C1 N1 115.88(16) . . ? O1' C9' C8' 108.58(14) . . ? O1' C9' C20' 111.17(14) . . ? C8' C9' C20' 109.24(15) . . ? O1' C9' C10' 104.87(14) . . ? C8' C9' C10' 110.88(15) . . ? C20' C9' C10' 112.01(14) . . ? C25 C20 C21 119.22(17) . . ? C25 C20 C9 122.68(16) . . ? C21 C20 C9 118.03(17) . . ? C2 C3 C4 120.03(17) . . ? C6 C5 C4 120.60(18) . . ? C3' C2' C1' 119.54(18) . . ? C5 C6 C1 119.84(17) . . ? C15 C10 C11 118.96(18) . . ? C15 C10 C9 121.04(17) . . ? C11 C10 C9 119.97(17) . . ? C7' C8' C9' 173.72(19) . . ? C3 C4 C5 119.29(16) . . ? C3 C4 C7 121.88(16) . . ? C5 C4 C7 118.78(17) . . ? C22' C21' C20' 120.4(2) . . ? C2' C3' C4' 120.71(17) . . ? C13 C14 C15 120.5(2) . . ? C6' C1' C2' 120.20(17) . . ? C6' C1' N1' 116.20(16) . . ? C2' C1' N1' 123.59(17) . . ? C10' C11' C12' 121.13(18) . . ? C3 C2 C1 120.28(18) . . ? C10 C15 C14 120.34(19) . . ? C1' C6' C5' 119.99(17) . . ? C12 C11 C10 120.18(19) . . ? C6' C5' C4' 120.46(18) . . ? C20' C25' C24' 119.87(19) . . ? C11 C12 C13 120.73(19) . . ? C10' C15' C14' 119.98(19) . . ? C14 C13 C12 119.23(19) . . ? C22 C21 C20 120.2(2) . . ? C20 C25 C24 120.28(19) . . ? C24' C23' C22' 119.6(2) . . ? C11' C12' C13' 120.06(19) . . ? C14' C13' C12' 119.17(18) . . ? C23' C22' C21' 120.4(2) . . ? C13' C14' C15' 120.95(19) . . ? C23' C24' C25' 120.5(2) . . ? C23 C24 C25 120.2(2) . . ? C23 C22 C21 120.2(2) . . ? C24 C23 C22 119.88(19) . . ? C1B N1B C3B 120.21(19) . . ? C1B N1B C2B 122.51(18) . . ? C3B N1B C2B 117.23(18) . . ? O1B C1B N1B 125.1(2) . . ? O1A C1A N1A 125.7(3) . . ? C1A N1A C2A 121.7(2) . . ? C1A N1A C3A 122.0(2) . . ? C2A N1A C3A 116.36(18) . . ? 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 C9 C8 C7 C4 50(4) . . . . ? C7 C8 C9 O1 -81.5(17) . . . . ? C7 C8 C9 C10 34.7(18) . . . . ? C7 C8 C9 C20 156.6(17) . . . . ? C8' C7' C4' C5' 7(4) . . . . ? C8' C7' C4' C3' -173(4) . . . . ? N1 N1 C1 C6 12.6(3) 2_576 . . . ? N1 N1 C1 C2 -167.5(2) 2_576 . . . ? C25' C20' C9' O1' -158.18(15) . . . . ? C21' C20' C9' O1' 25.4(2) . . . . ? C25' C20' C9' C8' -38.4(2) . . . . ? C21' C20' C9' C8' 145.15(16) . . . . ? C25' C20' C9' C10' 84.9(2) . . . . ? C21' C20' C9' C10' -91.61(19) . . . . ? C11' C10' C9' O1' 74.3(2) . . . . ? C15' C10' C9' O1' -99.7(2) . . . . ? C11' C10' C9' C8' -42.7(2) . . . . ? C15' C10' C9' C8' 143.29(18) . . . . ? C11' C10' C9' C20' -165.06(16) . . . . ? C15' C10' C9' C20' 21.0(2) . . . . ? O1 C9 C20 C25 -119.26(19) . . . . ? C8 C9 C20 C25 2.6(2) . . . . ? C10 C9 C20 C25 121.94(19) . . . . ? O1 C9 C20 C21 57.7(2) . . . . ? C8 C9 C20 C21 179.55(17) . . . . ? C10 C9 C20 C21 -61.1(2) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C2 C1 C6 C5 1.9(3) . . . . ? N1 C1 C6 C5 -178.27(18) . . . . ? O1 C9 C10 C15 -5.0(2) . . . . ? C8 C9 C10 C15 -122.38(18) . . . . ? C20 C9 C10 C15 115.14(18) . . . . ? O1 C9 C10 C11 173.20(15) . . . . ? C8 C9 C10 C11 55.8(2) . . . . ? C20 C9 C10 C11 -66.7(2) . . . . ? C4' C7' C8' C9' -14(6) . . . . ? O1' C9' C8' C7' 41.1(19) . . . . ? C20' C9' C8' C7' -80.2(19) . . . . ? C10' C9' C8' C7' 155.9(18) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 C7 177.82(18) . . . . ? C6 C5 C4 C3 -1.4(3) . . . . ? C6 C5 C4 C7 -179.01(18) . . . . ? C8 C7 C4 C3 -144(3) . . . . ? C8 C7 C4 C5 34(3) . . . . ? C25' C20' C21' C22' -0.7(3) . . . . ? C9' C20' C21' C22' 175.83(16) . . . . ? C1' C2' C3' C4' 0.9(3) . . . . ? C5' C4' C3' C2' -3.4(3) . . . . ? C7' C4' C3' C2' 176.98(18) . . . . ? C3' C2' C1' C6' 3.0(3) . . . . ? C3' C2' C1' N1' -175.94(17) . . . . ? N1' N1' C1' C6' -162.5(2) 2_476 . . . ? N1' N1' C1' C2' 16.5(3) 2_476 . . . ? C15' C10' C11' C12' -0.2(3) . . . . ? C9' C10' C11' C12' -174.36(17) . . . . ? C4 C3 C2 C1 1.9(3) . . . . ? C6 C1 C2 C3 -3.0(3) . . . . ? N1 C1 C2 C3 177.15(17) . . . . ? C11 C10 C15 C14 -1.4(3) . . . . ? C9 C10 C15 C14 176.80(16) . . . . ? C13 C14 C15 C10 0.2(3) . . . . ? C2' C1' C6' C5' -4.5(3) . . . . ? N1' C1' C6' C5' 174.56(18) . . . . ? C15 C10 C11 C12 1.4(3) . . . . ? C9 C10 C11 C12 -176.81(16) . . . . ? C1' C6' C5' C4' 2.0(3) . . . . ? C3' C4' C5' C6' 1.9(3) . . . . ? C7' C4' C5' C6' -178.43(18) . . . . ? C21' C20' C25' C24' 1.0(3) . . . . ? C9' C20' C25' C24' -175.50(16) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11' C10' C15' C14' -0.5(3) . . . . ? C9' C10' C15' C14' 173.48(18) . . . . ? C15 C14 C13 C12 1.1(3) . . . . ? C11 C12 C13 C14 -1.1(3) . . . . ? C25 C20 C21 C22 0.9(3) . . . . ? C9 C20 C21 C22 -176.23(18) . . . . ? C21 C20 C25 C24 -0.6(3) . . . . ? C9 C20 C25 C24 176.35(18) . . . . ? C10' C11' C12' C13' 0.9(3) . . . . ? C11' C12' C13' C14' -0.8(3) . . . . ? C24' C23' C22' C21' 1.1(3) . . . . ? C20' C21' C22' C23' -0.3(3) . . . . ? C12' C13' C14' C15' 0.1(3) . . . . ? C10' C15' C14' C13' 0.6(3) . . . . ? C22' C23' C24' C25' -0.8(3) . . . . ? C20' C25' C24' C23' -0.2(3) . . . . ? C20 C25 C24 C23 -0.1(3) . . . . ? C20 C21 C22 C23 -0.4(3) . . . . ? C25 C24 C23 C22 0.6(3) . . . . ? C21 C22 C23 C24 -0.3(3) . . . . ? C3B N1B C1B O1B 0.6(4) . . . . ? C2B N1B C1B O1B -176.6(2) . . . . ? O1A C1A N1A C2A 179.7(3) . . . . ? O1A C1A N1A C3A 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.297 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.054