# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Ayesha Jacobs' 'L R Nassimbeni' 'Kanyisa L. Nohako' 'Gaelle Ramon' 'Jana H. Taljaard' _publ_contact_author_name 'Ayesha Jacobs' _publ_contact_author_email JACOBSA@CPUT.AC.ZA _publ_section_title ; Enclathration by a xanthenol host via solid-solid reactions: Structures and Kinetics ; # Attachment 'A1ACR_FINAL.CIF' data_c:\ctech_~1\a1acrid\a1acrid _database_code_depnum_ccdc_archive 'CCDC 736889' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol acridine clathrate ; _chemical_formula_moiety 'C20 H16 O3.C13 H9 N1' _chemical_formula_sum 'C33 H25 N O3' _chemical_formula_weight 483.54 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 10.607(2) _cell_length_b 11.247(2) _cell_length_c 11.967(2) _cell_angle_alpha 96.17(3) _cell_angle_beta 110.43(3) _cell_angle_gamma 111.08(3) _cell_volume 1203.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.27 _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 20116 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.71 _reflns_number_total 4553 _reflns_number_gt 3347 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _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^)+(0.0589P)^2^+0.1644P] 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 4553 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.006 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 0.14651(12) 0.12321(10) 0.61730(10) 0.0314(3) Uani 1 1 d . . . C1 C 0.28458(15) 0.00924(13) 0.72858(13) 0.0240(3) Uani 1 1 d . . . O2 O 0.27703(12) -0.00740(10) 0.92617(9) 0.0283(3) Uani 1 1 d . . . C2 C 0.40206(16) -0.02671(14) 0.74778(15) 0.0299(4) Uani 1 1 d . . . H2 H 0.4200 -0.0786 0.8039 0.036 Uiso 1 1 calc R . . O3 O -0.14469(13) -0.59267(10) 0.60533(11) 0.0412(3) Uani 1 1 d . . . C3 C 0.49256(17) 0.01208(15) 0.68636(16) 0.0355(4) Uani 1 1 d . . . H3 H 0.5723 -0.0128 0.7006 0.043 Uiso 1 1 calc R . . C4 C 0.46674(18) 0.08731(15) 0.60395(16) 0.0368(4) Uani 1 1 d . . . H4 H 0.5298 0.1150 0.5627 0.044 Uiso 1 1 calc R . . C5 C 0.34967(18) 0.12213(14) 0.58156(15) 0.0328(4) Uani 1 1 d . . . H5 H 0.3306 0.1722 0.5239 0.039 Uiso 1 1 calc R . . C6 C 0.25998(16) 0.08300(14) 0.64458(14) 0.0257(3) Uani 1 1 d . . . C7 C 0.08672(15) 0.03778(13) 0.77915(13) 0.0231(3) Uani 1 1 d . . . C8 C 0.00619(16) 0.03245(14) 0.85057(15) 0.0282(4) Uani 1 1 d . . . H8 H 0.0166 -0.0145 0.9121 0.034 Uiso 1 1 calc R . . C9 C -0.08822(17) 0.09385(14) 0.83397(17) 0.0334(4) Uani 1 1 d . . . H9 H -0.1409 0.0903 0.8844 0.040 Uiso 1 1 calc R . . C10 C -0.10550(17) 0.16101(15) 0.74265(16) 0.0338(4) Uani 1 1 d . . . H10 H -0.1717 0.2020 0.7297 0.041 Uiso 1 1 calc R . . C11 C -0.02735(17) 0.16835(14) 0.67120(15) 0.0315(4) Uani 1 1 d . . . H11 H -0.0388 0.2146 0.6091 0.038 Uiso 1 1 calc R . . C12 C 0.06898(16) 0.10728(13) 0.69067(14) 0.0248(3) Uani 1 1 d . . . C13 C 0.18687(15) -0.03408(13) 0.79783(13) 0.0230(3) Uani 1 1 d . . . C14 C 0.09245(15) -0.18422(13) 0.74785(14) 0.0222(3) Uani 1 1 d . . . C15 C 0.11246(17) -0.27070(14) 0.81926(15) 0.0295(4) Uani 1 1 d . . . H15 H 0.1826 -0.2370 0.9034 0.035 Uiso 1 1 calc R . . C16 C 0.03071(17) -0.40622(15) 0.76867(16) 0.0328(4) Uani 1 1 d . . . H16 H 0.0448 -0.4646 0.8186 0.039 Uiso 1 1 calc R . . C17 C -0.07108(16) -0.45696(14) 0.64617(15) 0.0283(4) Uani 1 1 d . . . C18 C -0.09283(16) -0.37180(14) 0.57363(15) 0.0279(4) Uani 1 1 d . . . H18 H -0.1625 -0.4056 0.4894 0.033 Uiso 1 1 calc R . . C19 C -0.01149(16) -0.23647(13) 0.62575(14) 0.0260(3) Uani 1 1 d . . . H19 H -0.0275 -0.1781 0.5764 0.031 Uiso 1 1 calc R . . C20 C -0.24275(19) -0.65025(15) 0.47751(17) 0.0423(5) Uani 1 1 d . . . H20B H -0.3260 -0.6254 0.4581 0.064 Uiso 1 1 calc R . . H20A H -0.2809 -0.7467 0.4595 0.064 Uiso 1 1 calc R . . H20C H -0.1888 -0.6182 0.4271 0.064 Uiso 1 1 calc R . . N1G N 0.49243(13) 0.27236(11) 1.05212(12) 0.0271(3) Uani 1 1 d . . . C2G C 0.46424(16) 0.31885(14) 1.14508(14) 0.0262(3) Uani 1 1 d . . . C3G C 0.35650(17) 0.22913(15) 1.17706(15) 0.0321(4) Uani 1 1 d . . . H3G H 0.3079 0.1380 1.1340 0.039 Uiso 1 1 calc R . . C4G C 0.32229(18) 0.27204(16) 1.26839(16) 0.0364(4) Uani 1 1 d . . . H4G H 0.2494 0.2107 1.2877 0.044 Uiso 1 1 calc R . . C5G C 0.39424(17) 0.40736(16) 1.33517(15) 0.0352(4) Uani 1 1 d . . . H5G H 0.3697 0.4361 1.3990 0.042 Uiso 1 1 calc R . . C6G C 0.49808(17) 0.49572(15) 1.30791(15) 0.0320(4) Uani 1 1 d . . . H6G H 0.5457 0.5861 1.3532 0.038 Uiso 1 1 calc R . . C7G C 0.53685(16) 0.45551(14) 1.21285(14) 0.0262(3) Uani 1 1 d . . . C8G C 0.63872(16) 0.54318(14) 1.17879(14) 0.0278(4) Uani 1 1 d . . . H8G H 0.6878 0.6344 1.2214 0.033 Uiso 1 1 calc R . . C9G C 0.66912(15) 0.49826(14) 1.08294(14) 0.0259(3) Uani 1 1 d . . . C10G C 0.77042(16) 0.58341(15) 1.04240(15) 0.0296(4) Uani 1 1 d . . . H10G H 0.8184 0.6758 1.0807 0.036 Uiso 1 1 calc R . . C11G C 0.79953(17) 0.53521(16) 0.95046(15) 0.0336(4) Uani 1 1 d . . . H11G H 0.8689 0.5932 0.9258 0.040 Uiso 1 1 calc R . . C12G C 0.72595(18) 0.39750(16) 0.89085(16) 0.0346(4) Uani 1 1 d . . . H12G H 0.7470 0.3642 0.8264 0.041 Uiso 1 1 calc R . . C13G C 0.62581(17) 0.31253(15) 0.92448(15) 0.0305(4) Uani 1 1 d . . . H13G H 0.5773 0.2210 0.8827 0.037 Uiso 1 1 calc R . . C14G C 0.59311(16) 0.35925(14) 1.02140(14) 0.0254(3) Uani 1 1 d . . . H1 H 0.346(2) 0.077(2) 0.9565(19) 0.057(6) Uiso 1 1 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 0.0380(6) 0.0388(6) 0.0286(6) 0.0164(5) 0.0183(5) 0.0219(5) C1 0.0238(7) 0.0183(7) 0.0230(8) -0.0008(6) 0.0085(6) 0.0050(6) O2 0.0298(6) 0.0264(6) 0.0215(6) 0.0043(4) 0.0063(5) 0.0091(5) C2 0.0277(8) 0.0245(8) 0.0338(9) 0.0026(6) 0.0117(7) 0.0099(6) O3 0.0428(7) 0.0195(5) 0.0467(8) 0.0055(5) 0.0086(6) 0.0086(5) C3 0.0292(8) 0.0305(8) 0.0434(11) -0.0020(7) 0.0173(8) 0.0105(7) C4 0.0377(9) 0.0307(8) 0.0404(11) -0.0015(7) 0.0271(8) 0.0056(7) C5 0.0423(9) 0.0265(8) 0.0274(9) 0.0044(6) 0.0193(8) 0.0088(7) C6 0.0274(8) 0.0224(7) 0.0247(8) 0.0020(6) 0.0113(7) 0.0088(6) C7 0.0227(7) 0.0181(7) 0.0233(8) 0.0017(6) 0.0080(6) 0.0060(6) C8 0.0307(8) 0.0237(7) 0.0325(9) 0.0088(6) 0.0171(7) 0.0100(6) C9 0.0291(8) 0.0262(8) 0.0450(11) 0.0040(7) 0.0211(8) 0.0079(7) C10 0.0251(8) 0.0271(8) 0.0450(11) 0.0034(7) 0.0117(8) 0.0112(7) C11 0.0296(8) 0.0285(8) 0.0332(10) 0.0084(7) 0.0084(7) 0.0135(7) C12 0.0250(8) 0.0232(7) 0.0224(8) 0.0038(6) 0.0091(7) 0.0075(6) C13 0.0237(7) 0.0228(7) 0.0202(8) 0.0045(6) 0.0076(6) 0.0094(6) C14 0.0220(7) 0.0220(7) 0.0251(8) 0.0069(6) 0.0116(6) 0.0100(6) C15 0.0293(8) 0.0285(8) 0.0263(9) 0.0082(6) 0.0070(7) 0.0119(7) C16 0.0357(9) 0.0268(8) 0.0374(10) 0.0158(7) 0.0126(8) 0.0155(7) C17 0.0256(8) 0.0209(7) 0.0374(10) 0.0069(6) 0.0129(7) 0.0093(6) C18 0.0265(8) 0.0267(8) 0.0258(9) 0.0039(6) 0.0082(7) 0.0098(6) C19 0.0297(8) 0.0234(7) 0.0258(8) 0.0097(6) 0.0111(7) 0.0121(6) C20 0.0362(9) 0.0255(8) 0.0502(12) -0.0019(7) 0.0099(9) 0.0084(7) N1G 0.0269(7) 0.0233(6) 0.0269(7) 0.0043(5) 0.0092(6) 0.0089(5) C2G 0.0255(8) 0.0259(8) 0.0238(8) 0.0051(6) 0.0074(7) 0.0106(6) C3G 0.0319(8) 0.0263(8) 0.0295(9) 0.0053(6) 0.0111(7) 0.0056(7) C4G 0.0326(9) 0.0401(9) 0.0301(10) 0.0082(7) 0.0145(8) 0.0078(7) C5G 0.0326(9) 0.0426(9) 0.0270(9) 0.0032(7) 0.0133(7) 0.0133(7) C6G 0.0297(8) 0.0309(8) 0.0281(9) 0.0011(7) 0.0076(7) 0.0113(7) C7G 0.0234(7) 0.0256(8) 0.0237(8) 0.0040(6) 0.0051(6) 0.0096(6) C8G 0.0248(8) 0.0223(7) 0.0280(9) 0.0025(6) 0.0057(7) 0.0076(6) C9G 0.0217(7) 0.0254(8) 0.0254(9) 0.0054(6) 0.0050(6) 0.0096(6) C10G 0.0242(8) 0.0272(8) 0.0304(9) 0.0080(6) 0.0071(7) 0.0075(6) C11G 0.0269(8) 0.0370(9) 0.0349(10) 0.0127(7) 0.0131(7) 0.0107(7) C12G 0.0352(9) 0.0420(9) 0.0309(10) 0.0094(7) 0.0155(8) 0.0196(7) C13G 0.0315(8) 0.0275(8) 0.0302(9) 0.0039(6) 0.0112(7) 0.0130(7) C14G 0.0226(7) 0.0250(8) 0.0254(8) 0.0063(6) 0.0063(6) 0.0103(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.3816(18) . ? O1 C12 1.3824(18) . ? C1 C6 1.385(2) . ? C1 C2 1.397(2) . ? C1 C13 1.524(2) . ? O2 C13 1.4258(19) . ? O2 H1 0.90(2) . ? C2 C3 1.383(2) . ? C2 H2 0.9500 . ? O3 C17 1.3764(19) . ? O3 C20 1.426(2) . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(2) . ? C4 H4 0.9500 . ? C5 C6 1.392(2) . ? C5 H5 0.9500 . ? C7 C12 1.383(2) . ? C7 C8 1.396(2) . ? C7 C13 1.524(2) . ? C8 C9 1.381(2) . ? C8 H8 0.9500 . ? C9 C10 1.391(2) . ? C9 H9 0.9500 . ? C10 C11 1.373(2) . ? C10 H10 0.9500 . ? C11 C12 1.394(2) . ? C11 H11 0.9500 . ? C13 C14 1.536(2) . ? C14 C19 1.386(2) . ? C14 C15 1.386(2) . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 C17 1.383(2) . ? C16 H16 0.9500 . ? C17 C18 1.386(2) . ? C18 C19 1.388(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20B 0.9800 . ? C20 H20A 0.9800 . ? C20 H20C 0.9800 . ? N1G C2G 1.349(2) . ? N1G C14G 1.3532(19) . ? C2G C3G 1.425(2) . ? C2G C7G 1.435(2) . ? C3G C4G 1.360(2) . ? C3G H3G 0.9500 . ? C4G C5G 1.419(2) . ? C4G H4G 0.9500 . ? C5G C6G 1.357(2) . ? C5G H5G 0.9500 . ? C6G C7G 1.420(2) . ? C6G H6G 0.9500 . ? C7G C8G 1.391(2) . ? C8G C9G 1.388(2) . ? C8G H8G 0.9500 . ? C9G C10G 1.425(2) . ? C9G C14G 1.438(2) . ? C10G C11G 1.352(2) . ? C10G H10G 0.9500 . ? C11G C12G 1.422(2) . ? C11G H11G 0.9500 . ? C12G C13G 1.362(2) . ? C12G H12G 0.9500 . ? C13G C14G 1.422(2) . ? C13G H13G 0.9500 . ? 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 C6 O1 C12 118.27(12) . . ? C6 C1 C2 117.97(14) . . ? C6 C1 C13 121.99(13) . . ? C2 C1 C13 120.04(14) . . ? C13 O2 H1 110.8(13) . . ? C3 C2 C1 120.99(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C17 O3 C20 117.83(14) . . ? C2 C3 C4 119.89(15) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.28(15) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.19(16) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? O1 C6 C1 123.10(13) . . ? O1 C6 C5 115.24(14) . . ? C1 C6 C5 121.66(14) . . ? C12 C7 C8 117.57(13) . . ? C12 C7 C13 122.27(13) . . ? C8 C7 C13 120.14(13) . . ? C9 C8 C7 121.59(15) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 119.37(15) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 120.36(15) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.33(15) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? O1 C12 C7 122.83(13) . . ? O1 C12 C11 115.41(14) . . ? C7 C12 C11 121.76(14) . . ? O2 C13 C1 110.13(11) . . ? O2 C13 C7 110.54(11) . . ? C1 C13 C7 109.62(12) . . ? O2 C13 C14 107.52(12) . . ? C1 C13 C14 108.75(11) . . ? C7 C13 C14 110.24(11) . . ? C19 C14 C15 118.39(13) . . ? C19 C14 C13 119.40(13) . . ? C15 C14 C13 122.14(13) . . ? C14 C15 C16 120.42(15) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.52(15) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? O3 C17 C16 115.63(14) . . ? O3 C17 C18 124.59(14) . . ? C16 C17 C18 119.78(14) . . ? C17 C18 C19 119.11(15) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C14 C19 C18 121.77(14) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? O3 C20 H20B 109.5 . . ? O3 C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? O3 C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? C2G N1G C14G 118.18(12) . . ? N1G C2G C3G 118.91(13) . . ? N1G C2G C7G 122.95(14) . . ? C3G C2G C7G 118.14(14) . . ? C4G C3G C2G 120.94(14) . . ? C4G C3G H3G 119.5 . . ? C2G C3G H3G 119.5 . . ? C3G C4G C5G 120.76(15) . . ? C3G C4G H4G 119.6 . . ? C5G C4G H4G 119.6 . . ? C6G C5G C4G 120.05(15) . . ? C6G C5G H5G 120.0 . . ? C4G C5G H5G 120.0 . . ? C5G C6G C7G 121.14(14) . . ? C5G C6G H6G 119.4 . . ? C7G C6G H6G 119.4 . . ? C8G C7G C6G 123.16(13) . . ? C8G C7G C2G 117.85(14) . . ? C6G C7G C2G 118.96(14) . . ? C9G C8G C7G 120.44(13) . . ? C9G C8G H8G 119.8 . . ? C7G C8G H8G 119.8 . . ? C8G C9G C10G 123.09(13) . . ? C8G C9G C14G 118.00(14) . . ? C10G C9G C14G 118.90(14) . . ? C11G C10G C9G 121.23(14) . . ? C11G C10G H10G 119.4 . . ? C9G C10G H10G 119.4 . . ? C10G C11G C12G 119.81(15) . . ? C10G C11G H11G 120.1 . . ? C12G C11G H11G 120.1 . . ? C13G C12G C11G 121.14(15) . . ? C13G C12G H12G 119.4 . . ? C11G C12G H12G 119.4 . . ? C12G C13G C14G 120.73(14) . . ? C12G C13G H13G 119.6 . . ? C14G C13G H13G 119.6 . . ? N1G C14G C13G 119.27(13) . . ? N1G C14G C9G 122.57(14) . . ? C13G C14G C9G 118.16(14) . . ? 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 C6 C1 C2 C3 1.1(2) . . . . ? C13 C1 C2 C3 -179.68(13) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C12 O1 C6 C1 10.5(2) . . . . ? C12 O1 C6 C5 -169.40(12) . . . . ? C2 C1 C6 O1 179.43(12) . . . . ? C13 C1 C6 O1 0.2(2) . . . . ? C2 C1 C6 C5 -0.7(2) . . . . ? C13 C1 C6 C5 -179.94(13) . . . . ? C4 C5 C6 O1 179.41(13) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C12 C7 C8 C9 0.1(2) . . . . ? C13 C7 C8 C9 -178.45(13) . . . . ? C7 C8 C9 C10 1.0(2) . . . . ? C8 C9 C10 C11 -1.2(2) . . . . ? C9 C10 C11 C12 0.3(2) . . . . ? C6 O1 C12 C7 -8.68(19) . . . . ? C6 O1 C12 C11 170.21(12) . . . . ? C8 C7 C12 O1 177.76(13) . . . . ? C13 C7 C12 O1 -3.7(2) . . . . ? C8 C7 C12 C11 -1.1(2) . . . . ? C13 C7 C12 C11 177.48(13) . . . . ? C10 C11 C12 O1 -178.04(13) . . . . ? C10 C11 C12 C7 0.9(2) . . . . ? C6 C1 C13 O2 -132.91(14) . . . . ? C2 C1 C13 O2 47.88(16) . . . . ? C6 C1 C13 C7 -11.09(18) . . . . ? C2 C1 C13 C7 169.71(12) . . . . ? C6 C1 C13 C14 109.50(15) . . . . ? C2 C1 C13 C14 -69.71(16) . . . . ? C12 C7 C13 O2 134.36(13) . . . . ? C8 C7 C13 O2 -47.14(17) . . . . ? C12 C7 C13 C1 12.78(18) . . . . ? C8 C7 C13 C1 -168.72(12) . . . . ? C12 C7 C13 C14 -106.90(15) . . . . ? C8 C7 C13 C14 71.60(17) . . . . ? O2 C13 C14 C19 176.69(12) . . . . ? C1 C13 C14 C19 -64.09(16) . . . . ? C7 C13 C14 C19 56.12(17) . . . . ? O2 C13 C14 C15 -6.49(18) . . . . ? C1 C13 C14 C15 112.74(15) . . . . ? C7 C13 C14 C15 -127.05(15) . . . . ? C19 C14 C15 C16 0.5(2) . . . . ? C13 C14 C15 C16 -176.38(13) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? C20 O3 C17 C16 -175.50(14) . . . . ? C20 O3 C17 C18 4.5(2) . . . . ? C15 C16 C17 O3 179.29(14) . . . . ? C15 C16 C17 C18 -0.7(2) . . . . ? O3 C17 C18 C19 -179.98(13) . . . . ? C16 C17 C18 C19 0.0(2) . . . . ? C15 C14 C19 C18 -1.2(2) . . . . ? C13 C14 C19 C18 175.76(13) . . . . ? C17 C18 C19 C14 1.0(2) . . . . ? C14G N1G C2G C3G 178.83(14) . . . . ? C14G N1G C2G C7G -0.5(2) . . . . ? N1G C2G C3G C4G -178.64(15) . . . . ? C7G C2G C3G C4G 0.7(2) . . . . ? C2G C3G C4G C5G -0.6(3) . . . . ? C3G C4G C5G C6G 0.3(3) . . . . ? C4G C5G C6G C7G 0.1(3) . . . . ? C5G C6G C7G C8G 177.69(15) . . . . ? C5G C6G C7G C2G 0.0(2) . . . . ? N1G C2G C7G C8G 1.1(2) . . . . ? C3G C2G C7G C8G -178.17(14) . . . . ? N1G C2G C7G C6G 178.92(14) . . . . ? C3G C2G C7G C6G -0.4(2) . . . . ? C6G C7G C8G C9G -178.34(14) . . . . ? C2G C7G C8G C9G -0.6(2) . . . . ? C7G C8G C9G C10G 178.94(14) . . . . ? C7G C8G C9G C14G -0.4(2) . . . . ? C8G C9G C10G C11G 178.46(15) . . . . ? C14G C9G C10G C11G -2.2(2) . . . . ? C9G C10G C11G C12G 1.3(2) . . . . ? C10G C11G C12G C13G 0.1(2) . . . . ? C11G C12G C13G C14G -0.6(2) . . . . ? C2G N1G C14G C13G 179.43(14) . . . . ? C2G N1G C14G C9G -0.7(2) . . . . ? C12G C13G C14G N1G 179.63(14) . . . . ? C12G C13G C14G C9G -0.3(2) . . . . ? C8G C9G C14G N1G 1.1(2) . . . . ? C10G C9G C14G N1G -178.25(14) . . . . ? C8G C9G C14G C13G -178.99(14) . . . . ? C10G C9G C14G C13G 1.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.71 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.168 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.049 # Attachment 'A1HQ_final.cif' data_c:\ctech_~1\a18hydrq\a18hydrq _database_code_depnum_ccdc_archive 'CCDC 736890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol 8-hydroxyquinoline clathrate ; _chemical_formula_moiety 'C20 H16 O3.C4 H3 N O0.5' _chemical_formula_sum 'C24 H18.50 N O3.50' _chemical_formula_weight 376.90 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 8.3982(17) _cell_length_b 8.9905(18) _cell_length_c 12.954(3) _cell_angle_alpha 96.36(3) _cell_angle_beta 91.64(3) _cell_angle_gamma 109.14(3) _cell_volume 916.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.29 _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 395 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 13605 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.64 _reflns_number_total 3435 _reflns_number_gt 2556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _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^)+(0.0723P)^2^+0.6952P] 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 N/A _refine_ls_number_reflns 3435 _refine_ls_number_parameters 268 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.009 _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 -0.08802(18) -0.01682(16) 0.61799(12) 0.0291(4) Uani 1 1 d . . . C1 C 0.2072(3) 0.1227(2) 0.67478(16) 0.0228(5) Uani 1 1 d . . . H1 H 0.200(2) 0.189(2) 0.4882(12) 0.054(8) Uiso 1 1 d D . . O2 O 0.27472(17) 0.27981(17) 0.53193(11) 0.0250(4) Uani 1 1 d D . . C2 C 0.3551(3) 0.1114(3) 0.71974(17) 0.0279(5) Uani 1 1 d . . . H2 H 0.4540 0.2026 0.7297 0.034 Uiso 1 1 calc R . . O3 O 0.6412(2) 0.81494(19) 0.89347(12) 0.0359(4) Uani 1 1 d . . . C3 C 0.3611(3) -0.0297(3) 0.75012(18) 0.0322(5) Uani 1 1 d . . . H3 H 0.4635 -0.0351 0.7797 0.039 Uiso 1 1 calc R . . C4 C 0.2166(3) -0.1632(3) 0.73714(19) 0.0341(6) Uani 1 1 d . . . H4 H 0.2201 -0.2600 0.7582 0.041 Uiso 1 1 calc R . . C5 C 0.0688(3) -0.1554(3) 0.69396(19) 0.0311(5) Uani 1 1 d . . . H5 H -0.0304 -0.2464 0.6854 0.037 Uiso 1 1 calc R . . C6 C 0.0656(3) -0.0131(3) 0.66292(16) 0.0251(5) Uani 1 1 d . . . C7 C 0.0224(3) 0.2700(2) 0.61885(16) 0.0226(5) Uani 1 1 d . . . C8 C -0.0170(3) 0.4061(3) 0.60713(17) 0.0276(5) Uani 1 1 d . . . H8 H 0.0702 0.5064 0.6179 0.033 Uiso 1 1 calc R . . C9 C -0.1809(3) 0.3990(3) 0.58011(18) 0.0315(5) Uani 1 1 d . . . H9 H -0.2045 0.4936 0.5723 0.038 Uiso 1 1 calc R . . C10 C -0.3098(3) 0.2536(3) 0.56448(18) 0.0314(5) Uani 1 1 d . . . H10 H -0.4213 0.2481 0.5440 0.038 Uiso 1 1 calc R . . C11 C -0.2757(3) 0.1164(3) 0.57873(18) 0.0292(5) Uani 1 1 d . . . H11 H -0.3638 0.0166 0.5701 0.035 Uiso 1 1 calc R . . C12 C -0.1108(3) 0.1267(2) 0.60588(16) 0.0237(5) Uani 1 1 d . . . C13 C 0.2042(2) 0.2742(2) 0.63295(16) 0.0217(4) Uani 1 1 d . . . C14 C 0.3175(2) 0.4216(2) 0.70214(16) 0.0212(4) Uani 1 1 d . . . C15 C 0.4512(3) 0.5347(2) 0.66425(17) 0.0251(5) Uani 1 1 d . . . H15 H 0.4711 0.5231 0.5925 0.030 Uiso 1 1 calc R . . C16 C 0.5564(3) 0.6647(3) 0.73015(18) 0.0273(5) Uani 1 1 d . . . H16 H 0.6471 0.7413 0.7030 0.033 Uiso 1 1 calc R . . C17 C 0.5295(3) 0.6832(2) 0.83529(17) 0.0257(5) Uani 1 1 d . . . C18 C 0.3947(3) 0.5727(3) 0.87429(17) 0.0275(5) Uani 1 1 d . . . H18 H 0.3742 0.5850 0.9459 0.033 Uiso 1 1 calc R . . C19 C 0.2898(3) 0.4435(2) 0.80704(17) 0.0263(5) Uani 1 1 d . . . H19 H 0.1971 0.3686 0.8337 0.032 Uiso 1 1 calc R . . C20 C 0.6177(4) 0.8378(3) 1.00219(19) 0.0432(6) Uani 1 1 d . . . H20B H 0.5071 0.8499 1.0117 0.065 Uiso 1 1 calc R . . H20A H 0.7066 0.9334 1.0353 0.065 Uiso 1 1 calc R . . H20C H 0.6233 0.7456 1.0341 0.065 Uiso 1 1 calc R . . O1G O 1.0017(6) 0.1740(6) 1.0295(4) 0.0732(13) Uani 0.50 1 d P . . H1G H 1.0712 0.2218 1.0800 0.088 Uiso 0.50 1 calc PR . . C2G C 0.9532(4) 0.2775(5) 0.9835(3) 0.0689(10) Uani 1 1 d . . . C3G C 1.1966(5) 0.6461(6) 1.1503(3) 0.0866(14) Uani 1 1 d . . . H3G H 1.2739 0.6798 1.2100 0.104 Uiso 1 1 calc R . . N4G N 1.1299(4) 0.4829(5) 1.1131(3) 0.0957(12) Uani 1 1 d . . . C5G C 1.0249(3) 0.4482(4) 1.0260(2) 0.0536(8) Uani 1 1 d . . . C6G C 0.8488(4) 0.2370(5) 0.8993(3) 0.0797(13) Uani 1 1 d . . . H6G H 0.8028 0.1284 0.8709 0.096 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 O1 0.0211(8) 0.0204(8) 0.0436(10) 0.0019(7) -0.0054(7) 0.0051(6) C1 0.0226(10) 0.0220(10) 0.0237(11) -0.0005(8) 0.0010(8) 0.0084(9) O2 0.0226(7) 0.0256(8) 0.0242(8) 0.0013(6) 0.0032(6) 0.0050(6) C2 0.0241(11) 0.0259(11) 0.0325(12) 0.0009(9) -0.0021(9) 0.0079(9) O3 0.0345(9) 0.0313(9) 0.0311(9) -0.0021(7) -0.0028(7) -0.0013(7) C3 0.0295(12) 0.0329(13) 0.0372(13) 0.0023(10) -0.0051(10) 0.0157(10) C4 0.0386(13) 0.0253(12) 0.0417(14) 0.0066(10) -0.0019(11) 0.0146(10) C5 0.0291(12) 0.0214(11) 0.0405(13) 0.0034(9) 0.0001(10) 0.0057(9) C6 0.0225(11) 0.0260(11) 0.0273(11) 0.0006(9) -0.0011(8) 0.0100(9) C7 0.0197(10) 0.0245(11) 0.0235(11) 0.0026(8) 0.0004(8) 0.0076(9) C8 0.0244(11) 0.0233(11) 0.0341(12) 0.0033(9) 0.0017(9) 0.0068(9) C9 0.0298(12) 0.0302(12) 0.0392(13) 0.0073(10) 0.0031(10) 0.0156(10) C10 0.0225(11) 0.0380(13) 0.0362(13) 0.0027(10) -0.0004(9) 0.0144(10) C11 0.0208(11) 0.0291(12) 0.0348(13) 0.0004(10) -0.0011(9) 0.0061(9) C12 0.0235(11) 0.0219(11) 0.0259(11) 0.0011(8) 0.0004(8) 0.0087(9) C13 0.0198(10) 0.0221(11) 0.0233(11) 0.0030(8) 0.0027(8) 0.0069(8) C14 0.0193(10) 0.0204(10) 0.0256(11) 0.0037(8) 0.0003(8) 0.0087(8) C15 0.0217(10) 0.0265(11) 0.0265(11) 0.0029(9) 0.0028(8) 0.0073(9) C16 0.0210(10) 0.0255(11) 0.0332(12) 0.0053(9) 0.0044(9) 0.0040(9) C17 0.0227(11) 0.0219(11) 0.0306(12) 0.0003(9) -0.0040(9) 0.0062(9) C18 0.0303(12) 0.0270(11) 0.0237(11) 0.0032(9) 0.0024(9) 0.0075(9) C19 0.0236(11) 0.0228(11) 0.0307(12) 0.0053(9) 0.0047(9) 0.0045(9) C20 0.0494(16) 0.0375(14) 0.0294(13) -0.0057(11) -0.0040(11) 0.0004(12) O1G 0.048(3) 0.095(4) 0.067(3) 0.009(3) 0.001(2) 0.012(3) C2G 0.055(2) 0.076(2) 0.062(2) 0.0079(19) 0.0269(18) 0.0016(18) C3G 0.061(2) 0.102(3) 0.052(2) -0.008(2) 0.0166(17) -0.030(2) N4G 0.0463(17) 0.164(4) 0.069(2) 0.032(2) 0.0169(15) 0.017(2) C5G 0.0344(14) 0.087(2) 0.0355(16) 0.0122(14) 0.0105(12) 0.0129(15) C6G 0.055(2) 0.091(3) 0.058(2) -0.010(2) 0.0291(18) -0.019(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 O1 C6 1.389(2) . ? O1 C12 1.390(2) . ? C1 C6 1.388(3) . ? C1 C2 1.395(3) . ? C1 C13 1.528(3) . ? O2 C13 1.451(2) . ? O2 H1 0.960(2) . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? O3 C17 1.373(3) . ? O3 C20 1.429(3) . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.373(3) . ? C4 H4 0.9500 . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C7 C8 1.390(3) . ? C7 C12 1.391(3) . ? C7 C13 1.521(3) . ? C8 C9 1.389(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C13 C14 1.525(3) . ? C14 C19 1.389(3) . ? C14 C15 1.389(3) . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C17 1.388(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C18 C19 1.394(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20B 0.9800 . ? C20 H20A 0.9800 . ? C20 H20C 0.9800 . ? O1G C2G 1.321(6) . ? O1G H1G 0.8400 . ? C2G C6G 1.319(5) . ? C2G C5G 1.486(5) . ? C3G N4G 1.411(6) . ? C3G C6G 1.435(6) 2_767 ? C3G H3G 0.9500 . ? N4G C5G 1.353(4) . ? C5G C5G 1.370(6) 2_767 ? C6G C3G 1.435(6) 2_767 ? C6G H6G 0.9500 . ? 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 C6 O1 C12 118.23(16) . . ? C6 C1 C2 117.15(19) . . ? C6 C1 C13 121.16(18) . . ? C2 C1 C13 121.55(19) . . ? C13 O2 H1 105.3(10) . . ? C3 C2 C1 121.5(2) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C17 O3 C20 117.22(19) . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 O1 122.33(18) . . ? C1 C6 C5 122.12(19) . . ? O1 C6 C5 115.54(19) . . ? C8 C7 C12 116.96(19) . . ? C8 C7 C13 121.71(18) . . ? C12 C7 C13 120.98(18) . . ? C9 C8 C7 121.6(2) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 119.9(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.1(2) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 O1 115.19(18) . . ? C11 C12 C7 122.49(19) . . ? O1 C12 C7 122.31(18) . . ? O2 C13 C7 108.32(16) . . ? O2 C13 C14 105.95(16) . . ? C7 C13 C14 113.26(16) . . ? O2 C13 C1 108.61(15) . . ? C7 C13 C1 109.35(16) . . ? C14 C13 C1 111.16(16) . . ? C19 C14 C15 118.21(19) . . ? C19 C14 C13 119.65(18) . . ? C15 C14 C13 122.12(18) . . ? C14 C15 C16 120.8(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 120.3(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? O3 C17 C16 115.62(19) . . ? O3 C17 C18 124.7(2) . . ? C16 C17 C18 119.7(2) . . ? C17 C18 C19 119.2(2) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C14 C19 C18 121.7(2) . . ? C14 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? O3 C20 H20B 109.5 . . ? O3 C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? O3 C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? C2G O1G H1G 109.5 . . ? C6G C2G O1G 122.9(4) . . ? C6G C2G C5G 118.5(4) . . ? O1G C2G C5G 118.5(4) . . ? N4G C3G C6G 122.1(4) . 2_767 ? N4G C3G H3G 119.0 . . ? C6G C3G H3G 119.0 2_767 . ? C5G N4G C3G 114.2(4) . . ? N4G C5G C5G 127.5(4) . 2_767 ? N4G C5G C2G 116.0(4) . . ? C5G C5G C2G 116.5(4) 2_767 . ? C2G C6G C3G 121.2(4) . 2_767 ? C2G C6G H6G 119.4 . . ? C3G C6G H6G 119.4 2_767 . ? 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 C6 C1 C2 C3 0.8(3) . . . . ? C13 C1 C2 C3 -174.8(2) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C2 C1 C6 O1 -179.14(18) . . . . ? C13 C1 C6 O1 -3.5(3) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C13 C1 C6 C5 175.50(19) . . . . ? C12 O1 C6 C1 -14.5(3) . . . . ? C12 O1 C6 C5 166.41(19) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C4 C5 C6 O1 178.7(2) . . . . ? C12 C7 C8 C9 -2.2(3) . . . . ? C13 C7 C8 C9 171.0(2) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 C11 1.8(3) . . . . ? C9 C10 C11 C12 -1.7(3) . . . . ? C10 C11 C12 O1 -179.64(19) . . . . ? C10 C11 C12 C7 -0.4(3) . . . . ? C6 O1 C12 C11 -168.60(19) . . . . ? C6 O1 C12 C7 12.1(3) . . . . ? C8 C7 C12 C11 2.3(3) . . . . ? C13 C7 C12 C11 -170.99(19) . . . . ? C8 C7 C12 O1 -178.48(19) . . . . ? C13 C7 C12 O1 8.2(3) . . . . ? C8 C7 C13 O2 -78.2(2) . . . . ? C12 C7 C13 O2 94.8(2) . . . . ? C8 C7 C13 C14 39.1(3) . . . . ? C12 C7 C13 C14 -147.98(19) . . . . ? C8 C7 C13 C1 163.64(19) . . . . ? C12 C7 C13 C1 -23.4(3) . . . . ? C6 C1 C13 O2 -96.8(2) . . . . ? C2 C1 C13 O2 78.6(2) . . . . ? C6 C1 C13 C7 21.2(3) . . . . ? C2 C1 C13 C7 -163.41(19) . . . . ? C6 C1 C13 C14 146.97(19) . . . . ? C2 C1 C13 C14 -37.6(3) . . . . ? O2 C13 C14 C19 -175.01(17) . . . . ? C7 C13 C14 C19 66.4(2) . . . . ? C1 C13 C14 C19 -57.2(2) . . . . ? O2 C13 C14 C15 3.6(2) . . . . ? C7 C13 C14 C15 -115.0(2) . . . . ? C1 C13 C14 C15 121.4(2) . . . . ? C19 C14 C15 C16 1.2(3) . . . . ? C13 C14 C15 C16 -177.44(18) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C20 O3 C17 C16 -179.9(2) . . . . ? C20 O3 C17 C18 1.1(3) . . . . ? C15 C16 C17 O3 179.57(18) . . . . ? C15 C16 C17 C18 -1.3(3) . . . . ? O3 C17 C18 C19 179.95(19) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? C15 C14 C19 C18 -1.6(3) . . . . ? C13 C14 C19 C18 177.07(18) . . . . ? C17 C18 C19 C14 0.6(3) . . . . ? C6G C3G N4G C5G 1.8(5) 2_767 . . . ? C3G N4G C5G C5G -1.9(5) . . . 2_767 ? C3G N4G C5G C2G 179.4(3) . . . . ? C6G C2G C5G N4G 179.4(3) . . . . ? O1G C2G C5G N4G -3.1(5) . . . . ? C6G C2G C5G C5G 0.5(5) . . . 2_767 ? O1G C2G C5G C5G 178.0(4) . . . 2_767 ? O1G C2G C6G C3G -177.9(4) . . . 2_767 ? C5G C2G C6G C3G -0.6(5) . . . 2_767 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.971 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.054 # Attachment 'A1NAPA_final.cif' data_c:\ctech_~1\kanyisa\a1ec6c~1\a1naphm _database_code_depnum_ccdc_archive 'CCDC 736891' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol 1-naphthylamine clathrate ; _chemical_formula_moiety 'C20 H16 O3.C5 H5 N0.5' _chemical_formula_sum 'C25 H20 N0.50 O3' _chemical_formula_weight 375.42 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 8.4231(17) _cell_length_b 9.0634(18) _cell_length_c 13.014(3) _cell_angle_alpha 96.60(3) _cell_angle_beta 91.87(3) _cell_angle_gamma 109.87(3) _cell_volume 925.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 395 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 15208 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.66 _reflns_number_total 3505 _reflns_number_gt 2418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _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^)+(0.2000P)^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 N/A _refine_ls_number_reflns 3505 _refine_ls_number_parameters 237 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1471 _refine_ls_R_factor_gt 0.1109 _refine_ls_wR_factor_ref 0.3939 _refine_ls_wR_factor_gt 0.3526 _refine_ls_goodness_of_fit_ref 1.583 _refine_ls_restrained_S_all 1.611 _refine_ls_shift/su_max 0.009 _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 0.0881(3) 0.0151(3) 0.8850(2) 0.0303(8) Uani 1 1 d . . . C1 C -0.0237(5) -0.2704(5) 0.8826(3) 0.0221(10) Uani 1 1 d . . . H1 H -0.223(4) -0.189(4) 1.016(4) 0.11(3) Uiso 1 1 d D . . O2 O -0.2771(3) -0.2834(3) 0.9682(2) 0.0270(8) Uani 1 1 d D . . C2 C 0.0148(5) -0.4059(5) 0.8930(3) 0.0291(10) Uani 1 1 d . . . H2 H -0.0728 -0.5064 0.8806 0.035 Uiso 1 1 calc R . . O3 O -0.6301(4) -0.8226(4) 0.6029(2) 0.0368(9) Uani 1 1 d . . . C3 C 0.1784(5) -0.3974(6) 0.9211(3) 0.0331(11) Uani 1 1 d . . . H3 H 0.2015 -0.4911 0.9297 0.040 Uiso 1 1 calc R . . C4 C 0.3087(5) -0.2509(6) 0.9366(3) 0.0316(11) Uani 1 1 d . . . H4 H 0.4207 -0.2443 0.9565 0.038 Uiso 1 1 calc R . . C5 C 0.2752(5) -0.1167(5) 0.9231(3) 0.0297(10) Uani 1 1 d . . . H5 H 0.3642 -0.0170 0.9319 0.036 Uiso 1 1 calc R . . C6 C 0.1100(5) -0.1269(5) 0.8964(3) 0.0245(10) Uani 1 1 d . . . C7 C -0.2077(5) -0.1259(5) 0.8271(3) 0.0238(10) Uani 1 1 d . . . C8 C -0.3564(5) -0.1160(5) 0.7813(3) 0.0282(10) Uani 1 1 d . . . H8 H -0.4556 -0.2077 0.7699 0.034 Uiso 1 1 calc R . . C9 C -0.3613(6) 0.0254(6) 0.7524(4) 0.0342(11) Uani 1 1 d . . . H9 H -0.4639 0.0310 0.7237 0.041 Uiso 1 1 calc R . . C10 C -0.2149(6) 0.1586(6) 0.7659(4) 0.0346(11) Uani 1 1 d . . . H10 H -0.2167 0.2551 0.7449 0.041 Uiso 1 1 calc R . . C11 C -0.0685(5) 0.1509(5) 0.8093(4) 0.0305(11) Uani 1 1 d . . . H11 H 0.0317 0.2417 0.8185 0.037 Uiso 1 1 calc R . . C12 C -0.0670(5) 0.0100(5) 0.8397(3) 0.0264(10) Uani 1 1 d . . . C13 C -0.2059(5) -0.2757(5) 0.8679(3) 0.0236(10) Uani 1 1 d . . . C14 C -0.3180(5) -0.4240(5) 0.7976(3) 0.0228(10) Uani 1 1 d . . . C15 C -0.4516(5) -0.5396(5) 0.8342(3) 0.0263(10) Uani 1 1 d . . . H15 H -0.4732 -0.5281 0.9054 0.032 Uiso 1 1 calc R . . C16 C -0.5539(5) -0.6720(5) 0.7675(3) 0.0291(10) Uani 1 1 d . . . H16 H -0.6443 -0.7509 0.7930 0.035 Uiso 1 1 calc R . . C17 C -0.5222(5) -0.6875(5) 0.6631(3) 0.0265(10) Uani 1 1 d . . . C18 C -0.3897(5) -0.5745(5) 0.6259(3) 0.0284(10) Uani 1 1 d . . . H18 H -0.3681 -0.5854 0.5548 0.034 Uiso 1 1 calc R . . C19 C -0.2882(5) -0.4443(5) 0.6939(3) 0.0262(10) Uani 1 1 d . . . H19 H -0.1959 -0.3672 0.6685 0.031 Uiso 1 1 calc R . . C20 C -0.6042(7) -0.8403(6) 0.4949(4) 0.0430(13) Uani 1 1 d . . . H20B H -0.6169 -0.7509 0.4640 0.065 Uiso 1 1 calc R . . H20C H -0.6879 -0.9393 0.4604 0.065 Uiso 1 1 calc R . . H20A H -0.4900 -0.8429 0.4862 0.065 Uiso 1 1 calc R . . N1G N 0.051(2) -0.1504(14) 0.5356(13) 0.154(7) Uiso 0.50 1 d PD . . H1G1 H 0.0997 -0.0624 0.5783 0.185 Uiso 0.50 1 calc PR . . H1G2 H -0.0151 -0.1511 0.4817 0.185 Uiso 0.50 1 calc PR . . C1G C -0.1217(11) -0.4291(12) 0.4059(7) 0.111(3) Uiso 1 1 d D . . H1G H -0.1326 -0.3320 0.3924 0.134 Uiso 1 1 calc R . . C2G C -0.0153(8) -0.4393(8) 0.4852(5) 0.0693(19) Uiso 1 1 d D . . C3G C 0.0784(12) -0.2864(11) 0.5531(7) 0.120(3) Uiso 1 1 d D . . C4G C 0.1821(10) -0.2935(10) 0.6373(6) 0.085(2) Uiso 1 1 d D . . H4G H 0.2344 -0.2012 0.6858 0.103 Uiso 1 1 calc R . . C5G C 0.2095(13) -0.4296(12) 0.6513(8) 0.125(4) Uiso 1 1 d D . . H5G H 0.2935 -0.4256 0.7032 0.150 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 O1 0.0225(16) 0.0228(17) 0.0424(19) 0.0015(14) -0.0090(13) 0.0056(12) C1 0.0180(19) 0.023(2) 0.023(2) 0.0026(17) -0.0019(15) 0.0050(16) O2 0.0264(15) 0.0295(18) 0.0239(16) 0.0009(13) 0.0001(12) 0.0092(13) C2 0.027(2) 0.024(2) 0.036(2) -0.0005(19) 0.0013(18) 0.0088(18) O3 0.0381(19) 0.0255(19) 0.0355(19) -0.0047(14) -0.0027(14) 0.0000(14) C3 0.035(2) 0.035(3) 0.036(3) 0.004(2) 0.0001(19) 0.020(2) C4 0.022(2) 0.040(3) 0.036(3) 0.005(2) -0.0004(18) 0.0145(19) C5 0.020(2) 0.031(3) 0.033(2) 0.0023(19) 0.0004(17) 0.0039(18) C6 0.025(2) 0.021(2) 0.028(2) 0.0014(17) 0.0010(17) 0.0084(17) C7 0.022(2) 0.025(2) 0.025(2) 0.0013(17) 0.0014(16) 0.0085(17) C8 0.026(2) 0.025(2) 0.033(2) 0.0022(18) -0.0014(18) 0.0098(18) C9 0.035(2) 0.034(3) 0.036(3) 0.000(2) -0.006(2) 0.017(2) C10 0.040(3) 0.029(3) 0.038(3) 0.007(2) -0.001(2) 0.015(2) C11 0.028(2) 0.019(2) 0.042(3) 0.0017(19) -0.0014(19) 0.0053(17) C12 0.023(2) 0.028(2) 0.028(2) 0.0002(18) -0.0018(17) 0.0099(18) C13 0.020(2) 0.024(2) 0.027(2) 0.0015(18) 0.0003(16) 0.0076(17) C14 0.021(2) 0.021(2) 0.026(2) 0.0011(17) -0.0025(16) 0.0086(17) C15 0.023(2) 0.026(2) 0.027(2) 0.0030(18) -0.0005(17) 0.0066(17) C16 0.023(2) 0.024(2) 0.036(2) 0.0046(19) 0.0032(18) 0.0031(18) C17 0.023(2) 0.024(2) 0.030(2) 0.0023(18) -0.0034(17) 0.0063(17) C18 0.030(2) 0.030(3) 0.025(2) 0.0015(18) 0.0028(17) 0.0113(18) C19 0.027(2) 0.024(2) 0.026(2) 0.0046(18) 0.0051(17) 0.0050(17) C20 0.048(3) 0.037(3) 0.033(3) -0.004(2) 0.002(2) 0.004(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 O1 C6 1.384(5) . ? O1 C12 1.400(5) . ? C1 C6 1.389(6) . ? C1 C2 1.392(6) . ? C1 C13 1.524(5) . ? O2 C13 1.453(5) . ? O2 H1 0.9600(5) . ? C2 C3 1.389(6) . ? C2 H2 0.9500 . ? O3 C17 1.384(5) . ? O3 C20 1.429(6) . ? C3 C4 1.393(7) . ? C3 H3 0.9500 . ? C4 C5 1.367(6) . ? C4 H4 0.9500 . ? C5 C6 1.393(6) . ? C5 H5 0.9500 . ? C7 C12 1.377(6) . ? C7 C8 1.405(6) . ? C7 C13 1.519(6) . ? C8 C9 1.389(6) . ? C8 H8 0.9500 . ? C9 C10 1.391(7) . ? C9 H9 0.9500 . ? C10 C11 1.367(6) . ? C10 H10 0.9500 . ? C11 C12 1.384(6) . ? C11 H11 0.9500 . ? C13 C14 1.528(6) . ? C14 C19 1.384(6) . ? C14 C15 1.392(6) . ? C15 C16 1.395(6) . ? C15 H15 0.9500 . ? C16 C17 1.394(6) . ? C16 H16 0.9500 . ? C17 C18 1.379(6) . ? C18 C19 1.390(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C20 H20A 0.9800 . ? N1G C3G 1.370(9) . ? N1G H1G1 0.8800 . ? N1G H1G2 0.8800 . ? C1G C5G 1.358(13) 2_546 ? C1G C2G 1.376(8) . ? C1G H1G 0.9500 . ? C2G C2G 1.308(12) 2_546 ? C2G C3G 1.501(8) . ? C3G C4G 1.400(8) . ? C4G C5G 1.361(8) . ? C4G H4G 0.9500 . ? C5G C1G 1.358(13) 2_546 ? C5G H5G 0.9500 . ? 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 C6 O1 C12 118.1(3) . . ? C6 C1 C2 117.2(4) . . ? C6 C1 C13 120.8(4) . . ? C2 C1 C13 121.8(4) . . ? C13 O2 H1 113(4) . . ? C3 C2 C1 121.5(4) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C17 O3 C20 116.8(4) . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? O1 C6 C1 122.4(4) . . ? O1 C6 C5 115.6(4) . . ? C1 C6 C5 122.0(4) . . ? C12 C7 C8 116.8(4) . . ? C12 C7 C13 121.6(4) . . ? C8 C7 C13 121.4(4) . . ? C9 C8 C7 121.3(4) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 119.5(4) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 122.8(4) . . ? C7 C12 O1 122.0(4) . . ? C11 C12 O1 115.2(4) . . ? O2 C13 C7 109.1(3) . . ? O2 C13 C1 108.3(3) . . ? C7 C13 C1 109.4(3) . . ? O2 C13 C14 106.0(3) . . ? C7 C13 C14 111.5(3) . . ? C1 C13 C14 112.4(3) . . ? C19 C14 C15 118.5(4) . . ? C19 C14 C13 119.4(4) . . ? C15 C14 C13 122.1(4) . . ? C14 C15 C16 120.7(4) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 119.4(4) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C18 C17 O3 124.1(4) . . ? C18 C17 C16 120.6(4) . . ? O3 C17 C16 115.3(4) . . ? C17 C18 C19 119.1(4) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C14 C19 C18 121.7(4) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? O3 C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? C3G N1G H1G1 120.0 . . ? C3G N1G H1G2 120.0 . . ? H1G1 N1G H1G2 120.0 . . ? C5G C1G C2G 113.9(9) 2_546 . ? C5G C1G H1G 123.1 2_546 . ? C2G C1G H1G 123.1 . . ? C2G C2G C1G 131.3(9) 2_546 . ? C2G C2G C3G 113.3(8) 2_546 . ? C1G C2G C3G 115.4(7) . . ? N1G C3G C4G 122.9(10) . . ? N1G C3G C2G 119.9(9) . . ? C4G C3G C2G 117.0(8) . . ? C5G C4G C3G 121.5(9) . . ? C5G C4G H4G 119.2 . . ? C3G C4G H4G 119.2 . . ? C1G C5G C4G 122.6(9) 2_546 . ? C1G C5G H5G 118.7 2_546 . ? C4G C5G H5G 118.7 . . ? 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 C6 C1 C2 C3 3.2(6) . . . . ? C13 C1 C2 C3 -170.6(4) . . . . ? C1 C2 C3 C4 -1.8(7) . . . . ? C2 C3 C4 C5 -0.7(7) . . . . ? C3 C4 C5 C6 1.6(7) . . . . ? C12 O1 C6 C1 -12.0(6) . . . . ? C12 O1 C6 C5 168.2(4) . . . . ? C2 C1 C6 O1 178.0(4) . . . . ? C13 C1 C6 O1 -8.1(6) . . . . ? C2 C1 C6 C5 -2.3(6) . . . . ? C13 C1 C6 C5 171.6(4) . . . . ? C4 C5 C6 O1 179.6(4) . . . . ? C4 C5 C6 C1 -0.1(7) . . . . ? C12 C7 C8 C9 -1.3(6) . . . . ? C13 C7 C8 C9 174.2(4) . . . . ? C7 C8 C9 C10 2.1(7) . . . . ? C8 C9 C10 C11 -1.4(7) . . . . ? C9 C10 C11 C12 0.0(7) . . . . ? C8 C7 C12 C11 -0.1(6) . . . . ? C13 C7 C12 C11 -175.7(4) . . . . ? C8 C7 C12 O1 179.5(4) . . . . ? C13 C7 C12 O1 4.0(6) . . . . ? C10 C11 C12 C7 0.8(7) . . . . ? C10 C11 C12 O1 -178.9(4) . . . . ? C6 O1 C12 C7 14.2(6) . . . . ? C6 O1 C12 C11 -166.1(4) . . . . ? C12 C7 C13 O2 96.8(4) . . . . ? C8 C7 C13 O2 -78.5(5) . . . . ? C12 C7 C13 C1 -21.4(5) . . . . ? C8 C7 C13 C1 163.2(4) . . . . ? C12 C7 C13 C14 -146.4(4) . . . . ? C8 C7 C13 C14 38.3(5) . . . . ? C6 C1 C13 O2 -95.4(4) . . . . ? C2 C1 C13 O2 78.2(5) . . . . ? C6 C1 C13 C7 23.4(5) . . . . ? C2 C1 C13 C7 -163.0(4) . . . . ? C6 C1 C13 C14 147.8(4) . . . . ? C2 C1 C13 C14 -38.6(5) . . . . ? O2 C13 C14 C19 175.6(3) . . . . ? C7 C13 C14 C19 57.0(5) . . . . ? C1 C13 C14 C19 -66.3(5) . . . . ? O2 C13 C14 C15 -3.7(5) . . . . ? C7 C13 C14 C15 -122.3(4) . . . . ? C1 C13 C14 C15 114.5(4) . . . . ? C19 C14 C15 C16 -0.6(6) . . . . ? C13 C14 C15 C16 178.6(4) . . . . ? C14 C15 C16 C17 -0.5(6) . . . . ? C20 O3 C17 C18 -2.5(6) . . . . ? C20 O3 C17 C16 178.4(4) . . . . ? C15 C16 C17 C18 0.9(6) . . . . ? C15 C16 C17 O3 -180.0(3) . . . . ? O3 C17 C18 C19 -179.2(4) . . . . ? C16 C17 C18 C19 -0.2(6) . . . . ? C15 C14 C19 C18 1.4(6) . . . . ? C13 C14 C19 C18 -177.9(3) . . . . ? C17 C18 C19 C14 -0.9(6) . . . . ? C5G C1G C2G C2G -0.1(14) 2_546 . . 2_546 ? C5G C1G C2G C3G -177.5(9) 2_546 . . . ? C2G C2G C3G N1G -176.0(12) 2_546 . . . ? C1G C2G C3G N1G 1.9(14) . . . . ? C2G C2G C3G C4G -0.6(12) 2_546 . . . ? C1G C2G C3G C4G 177.3(8) . . . . ? N1G C3G C4G C5G -178.6(12) . . . . ? C2G C3G C4G C5G 6.2(14) . . . . ? C3G C4G C5G C1G -9.3(16) . . . 2_546 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.466 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.121 # Attachment 'A1TEDA_final.cif' data_c:\ctech_~1\a1teda\a1teda _database_code_depnum_ccdc_archive 'CCDC 736892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9-(4-methoxyphenyl)-9H-xanthen-9-ol triethylenediamine clathrate ; _chemical_formula_moiety 'C20 H16 O3. C3 H6 N1' _chemical_formula_sum 'C23 H22 N O3' _chemical_formula_weight 360.42 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 9.0572(18) _cell_length_b 9.6751(19) _cell_length_c 10.501(2) _cell_angle_alpha 88.56(3) _cell_angle_beta 83.74(3) _cell_angle_gamma 85.45(3) _cell_volume 911.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 15587 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.66 _reflns_number_total 3431 _reflns_number_gt 2686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _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^)+(0.0517P)^2^+0.1519P] 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 3431 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.005 _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 0.54016(10) 0.72701(10) 0.09464(9) 0.0302(2) Uani 1 1 d . . . C1 C 0.29035(13) 0.84196(13) 0.11855(12) 0.0230(3) Uani 1 1 d . . . H1 H 0.327(2) 0.747(2) 0.3681(17) 0.057(5) Uiso 1 1 d . . . O2 O 0.25683(10) 0.81876(9) 0.34786(8) 0.0258(2) Uani 1 1 d . . . C2 C 0.15499(14) 0.86270(15) 0.06581(13) 0.0307(3) Uani 1 1 d . . . H2 H 0.0800 0.9278 0.1038 0.037 Uiso 1 1 calc R . . O3 O 0.01605(11) 1.44273(10) 0.31512(11) 0.0411(3) Uani 1 1 d . . . C3 C 0.12744(16) 0.79110(17) -0.04008(14) 0.0383(4) Uani 1 1 d . . . H3 H 0.0346 0.8074 -0.0743 0.046 Uiso 1 1 calc R . . C4 C 0.23523(17) 0.69567(18) -0.09622(15) 0.0412(4) Uani 1 1 d . . . H4 H 0.2155 0.6443 -0.1676 0.049 Uiso 1 1 calc R . . C5 C 0.37166(16) 0.67499(17) -0.04855(14) 0.0376(4) Uani 1 1 d . . . H5 H 0.4464 0.6101 -0.0872 0.045 Uiso 1 1 calc R . . C6 C 0.39836(14) 0.75002(14) 0.05635(12) 0.0264(3) Uani 1 1 d . . . C7 C 0.48289(13) 0.91125(13) 0.24945(12) 0.0218(3) Uani 1 1 d . . . C8 C 0.53897(15) 0.99831(14) 0.33257(13) 0.0291(3) Uani 1 1 d . . . H8 H 0.4721 1.0610 0.3829 0.035 Uiso 1 1 calc R . . C9 C 0.68978(15) 0.99579(15) 0.34378(15) 0.0351(3) Uani 1 1 d . . . H9 H 0.7257 1.0555 0.4019 0.042 Uiso 1 1 calc R . . C10 C 0.78830(15) 0.90576(16) 0.26976(14) 0.0350(4) Uani 1 1 d . . . H10 H 0.8920 0.9034 0.2774 0.042 Uiso 1 1 calc R . . C11 C 0.73628(14) 0.81973(16) 0.18526(13) 0.0323(3) Uani 1 1 d . . . H11 H 0.8039 0.7595 0.1330 0.039 Uiso 1 1 calc R . . C12 C 0.58387(13) 0.82160(13) 0.17691(12) 0.0239(3) Uani 1 1 d . . . C13 C 0.31608(13) 0.90596(13) 0.24459(12) 0.0206(3) Uani 1 1 d . . . C14 C 0.23498(13) 1.04983(13) 0.26168(12) 0.0211(3) Uani 1 1 d . . . C15 C 0.12551(13) 1.07849(14) 0.36269(13) 0.0259(3) Uani 1 1 d . . . H15 H 0.0986 1.0067 0.4221 0.031 Uiso 1 1 calc R . . C16 C 0.05484(15) 1.21031(14) 0.37817(14) 0.0303(3) Uani 1 1 d . . . H16 H -0.0197 1.2283 0.4479 0.036 Uiso 1 1 calc R . . C17 C 0.09281(14) 1.31620(13) 0.29194(13) 0.0283(3) Uani 1 1 d . . . C18 C 0.20187(14) 1.28941(14) 0.19036(13) 0.0289(3) Uani 1 1 d . . . H18 H 0.2286 1.3611 0.1308 0.035 Uiso 1 1 calc R . . C19 C 0.27162(14) 1.15675(14) 0.17653(13) 0.0263(3) Uani 1 1 d . . . H19 H 0.3464 1.1388 0.1069 0.032 Uiso 1 1 calc R . . C20 C 0.05220(18) 1.55479(16) 0.22990(19) 0.0497(5) Uani 1 1 d . . . H20A H 0.1587 1.5677 0.2271 0.075 Uiso 1 1 calc R . . H20B H -0.0058 1.6398 0.2601 0.075 Uiso 1 1 calc R . . H20C H 0.0285 1.5340 0.1439 0.075 Uiso 1 1 calc R . . N1G N 0.44202(12) 0.60286(11) 0.43748(11) 0.0304(3) Uani 1 1 d . . . C2G C 0.4151(4) 0.6234(3) 0.5809(3) 0.0470(8) Uani 0.50 1 d P . . H2G1 H 0.3065 0.6359 0.6070 0.056 Uiso 0.50 1 calc PR . . H2G2 H 0.4598 0.7086 0.6029 0.056 Uiso 0.50 1 calc PR . . C3G C 0.3212(3) 0.5327(4) 0.5123(4) 0.0462(9) Uani 0.50 1 d P . . H3G1 H 0.2562 0.4950 0.4539 0.055 Uiso 0.50 1 calc PR . . H3G2 H 0.2598 0.5995 0.5697 0.055 Uiso 0.50 1 calc PR . . C4G C 0.3828(4) 0.4740(3) 0.4132(4) 0.0467(8) Uani 0.50 1 d P . . H4G1 H 0.3963 0.4574 0.3199 0.056 Uiso 0.50 1 calc PR . . H4G2 H 0.2746 0.4807 0.4414 0.056 Uiso 0.50 1 calc PR . . C5G C 0.5174(4) 0.5011(3) 0.3446(3) 0.0421(8) Uani 0.50 1 d P . . H5G1 H 0.5970 0.5445 0.2890 0.050 Uiso 0.50 1 calc PR . . H5G2 H 0.4450 0.4696 0.2896 0.050 Uiso 0.50 1 calc PR . . C6G C 0.6077(3) 0.5862(4) 0.4079(4) 0.0477(9) Uani 0.50 1 d P . . H6G1 H 0.6501 0.6741 0.4258 0.057 Uiso 0.50 1 calc PR . . H6G2 H 0.6329 0.5669 0.3156 0.057 Uiso 0.50 1 calc PR . . C7G C 0.5414(4) 0.6503(3) 0.5169(4) 0.0481(9) Uani 0.50 1 d P . . H7G1 H 0.4869 0.7148 0.5806 0.058 Uiso 0.50 1 calc PR . . H7G2 H 0.6180 0.7011 0.4649 0.058 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0234(5) 0.0368(6) 0.0298(5) -0.0076(4) -0.0036(4) 0.0046(4) C1 0.0225(6) 0.0222(7) 0.0242(7) 0.0029(5) -0.0013(5) -0.0042(5) O2 0.0248(5) 0.0238(5) 0.0272(5) 0.0090(4) 0.0013(4) -0.0004(4) C2 0.0243(7) 0.0334(8) 0.0350(8) 0.0004(6) -0.0057(6) -0.0025(6) O3 0.0419(6) 0.0233(5) 0.0569(7) -0.0002(5) -0.0081(5) 0.0076(4) C3 0.0308(8) 0.0487(10) 0.0382(9) -0.0017(7) -0.0126(6) -0.0077(7) C4 0.0407(9) 0.0514(10) 0.0339(9) -0.0110(7) -0.0088(7) -0.0098(7) C5 0.0344(8) 0.0451(9) 0.0328(8) -0.0113(7) -0.0012(6) -0.0010(7) C6 0.0237(7) 0.0302(7) 0.0256(7) 0.0018(6) -0.0035(5) -0.0030(5) C7 0.0200(6) 0.0220(6) 0.0232(7) 0.0059(5) -0.0035(5) -0.0010(5) C8 0.0280(7) 0.0251(7) 0.0346(8) -0.0010(6) -0.0077(6) 0.0009(6) C9 0.0321(8) 0.0311(8) 0.0452(9) 0.0012(7) -0.0155(6) -0.0060(6) C10 0.0201(7) 0.0439(9) 0.0417(9) 0.0073(7) -0.0078(6) -0.0038(6) C11 0.0218(7) 0.0417(8) 0.0317(8) 0.0033(6) -0.0005(5) 0.0035(6) C12 0.0239(7) 0.0262(7) 0.0213(7) 0.0036(5) -0.0026(5) -0.0022(5) C13 0.0199(6) 0.0209(6) 0.0206(6) 0.0043(5) -0.0006(5) -0.0018(5) C14 0.0183(6) 0.0226(7) 0.0229(7) 0.0023(5) -0.0057(5) -0.0014(5) C15 0.0224(6) 0.0260(7) 0.0284(7) 0.0049(6) -0.0015(5) 0.0002(5) C16 0.0252(7) 0.0308(8) 0.0333(8) -0.0009(6) -0.0004(6) 0.0042(6) C17 0.0261(7) 0.0213(7) 0.0390(8) -0.0012(6) -0.0130(6) 0.0028(5) C18 0.0286(7) 0.0252(7) 0.0341(8) 0.0081(6) -0.0100(6) -0.0040(6) C19 0.0244(7) 0.0275(7) 0.0265(7) 0.0048(6) -0.0021(5) -0.0011(5) C20 0.0479(10) 0.0235(8) 0.0790(13) 0.0082(8) -0.0184(9) 0.0028(7) N1G 0.0329(6) 0.0248(6) 0.0314(7) 0.0057(5) 0.0001(5) 0.0044(5) C2G 0.072(2) 0.0299(17) 0.0353(18) 0.0008(14) 0.0006(16) 0.0123(16) C3G 0.0305(16) 0.051(2) 0.054(2) 0.0266(18) -0.0016(14) 0.0000(14) C4G 0.055(2) 0.0398(19) 0.050(2) 0.0015(16) -0.0246(17) -0.0058(15) C5G 0.059(2) 0.0379(17) 0.0266(16) 0.0005(13) -0.0034(14) 0.0134(15) C6G 0.0355(17) 0.047(2) 0.057(2) 0.0283(17) 0.0036(15) 0.0023(14) C7G 0.064(2) 0.0240(16) 0.061(2) -0.0010(15) -0.0252(19) -0.0051(15) _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 C12 1.3830(16) . ? O1 C6 1.3869(15) . ? C1 C6 1.3880(19) . ? C1 C2 1.3977(18) . ? C1 C13 1.5234(18) . ? O2 C13 1.4404(15) . ? O2 H1 0.94(2) . ? C2 C3 1.380(2) . ? C2 H2 0.9500 . ? O3 C17 1.3726(16) . ? O3 C20 1.4238(19) . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.381(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C7 C12 1.3872(19) . ? C7 C8 1.3896(19) . ? C7 C13 1.5222(16) . ? C8 C9 1.3820(19) . ? C8 H8 0.9500 . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C10 C11 1.376(2) . ? C10 H10 0.9500 . ? C11 C12 1.3914(18) . ? C11 H11 0.9500 . ? C13 C14 1.5267(17) . ? C14 C19 1.3866(18) . ? C14 C15 1.3881(18) . ? C15 C16 1.3859(19) . ? C15 H15 0.9500 . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 C18 1.387(2) . ? C18 C19 1.3886(19) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N1G C7G 1.402(3) . ? N1G C4G 1.435(4) . ? N1G C3G 1.476(3) . ? N1G C5G 1.478(3) . ? N1G C6G 1.496(3) . ? N1G C2G 1.515(3) . ? C2G C5G 1.542(4) 2_666 ? C2G C4G 1.997(5) 2_666 ? C2G H2G1 0.9900 . ? C2G H2G2 0.9900 . ? C3G C6G 1.547(4) 2_666 ? C3G H3G1 0.9900 . ? C3G H3G2 0.9900 . ? C4G C7G 1.545(4) 2_666 ? C4G C6G 1.962(5) 2_666 ? C4G C2G 1.997(5) 2_666 ? C4G H4G1 0.9900 . ? C4G H4G2 0.9900 . ? C5G C2G 1.542(4) 2_666 ? C5G H5G1 0.9900 . ? C5G H5G2 0.9900 . ? C6G C3G 1.547(4) 2_666 ? C6G C4G 1.962(5) 2_666 ? C6G H6G1 0.9900 . ? C6G H6G2 0.9900 . ? C7G C4G 1.545(4) 2_666 ? C7G H7G1 0.9900 . ? C7G H7G2 0.9900 . ? 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 C12 O1 C6 117.35(10) . . ? C6 C1 C2 116.86(12) . . ? C6 C1 C13 120.43(11) . . ? C2 C1 C13 122.50(12) . . ? C13 O2 H1 111.6(11) . . ? C3 C2 C1 121.71(13) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C17 O3 C20 117.73(12) . . ? C2 C3 C4 119.84(13) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.01(14) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.28(14) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? O1 C6 C5 115.47(12) . . ? O1 C6 C1 122.34(12) . . ? C5 C6 C1 122.18(12) . . ? C12 C7 C8 117.66(11) . . ? C12 C7 C13 120.63(11) . . ? C8 C7 C13 121.56(12) . . ? C9 C8 C7 121.55(13) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 119.61(14) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 120.16(13) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.52(13) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? O1 C12 C7 122.60(11) . . ? O1 C12 C11 115.91(12) . . ? C7 C12 C11 121.47(13) . . ? O2 C13 C7 109.34(10) . . ? O2 C13 C1 108.18(10) . . ? C7 C13 C1 108.83(10) . . ? O2 C13 C14 107.44(10) . . ? C7 C13 C14 111.13(10) . . ? C1 C13 C14 111.85(10) . . ? C19 C14 C15 118.16(12) . . ? C19 C14 C13 120.16(11) . . ? C15 C14 C13 121.68(11) . . ? C16 C15 C14 120.96(12) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 120.14(13) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? O3 C17 C18 124.58(13) . . ? O3 C17 C16 115.73(12) . . ? C18 C17 C16 119.69(12) . . ? C17 C18 C19 119.35(12) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C14 C19 C18 121.70(12) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C7G N1G C4G 137.3(2) . . ? C7G N1G C3G 111.5(2) . . ? C4G N1G C3G 50.9(2) . . ? C7G N1G C5G 111.6(2) . . ? C4G N1G C5G 56.9(2) . . ? C3G N1G C5G 106.6(2) . . ? C7G N1G C6G 56.4(2) . . ? C4G N1G C6G 108.5(2) . . ? C3G N1G C6G 139.41(18) . . ? C5G N1G C6G 57.5(2) . . ? C7G N1G C2G 52.9(2) . . ? C4G N1G C2G 106.4(2) . . ? C3G N1G C2G 60.9(2) . . ? C5G N1G C2G 139.65(17) . . ? C6G N1G C2G 105.2(2) . . ? N1G C2G C5G 111.6(2) . 2_666 ? N1G C2G C4G 85.63(19) . 2_666 ? C5G C2G C4G 43.84(18) 2_666 2_666 ? N1G C2G H2G1 109.3 . . ? C5G C2G H2G1 109.3 2_666 . ? C4G C2G H2G1 153.1 2_666 . ? N1G C2G H2G2 109.3 . . ? C5G C2G H2G2 109.3 2_666 . ? C4G C2G H2G2 86.7 2_666 . ? H2G1 C2G H2G2 108.0 . . ? N1G C3G C6G 108.3(2) . 2_666 ? N1G C3G H3G1 110.0 . . ? C6G C3G H3G1 110.0 2_666 . ? N1G C3G H3G2 110.0 . . ? C6G C3G H3G2 110.0 2_666 . ? H3G1 C3G H3G2 108.4 . . ? N1G C4G C7G 112.6(2) . 2_666 ? N1G C4G C6G 91.0(2) . 2_666 ? C7G C4G C6G 44.10(19) 2_666 2_666 ? N1G C4G C2G 89.7(2) . 2_666 ? C7G C4G C2G 40.73(19) 2_666 2_666 ? C6G C4G C2G 74.31(17) 2_666 2_666 ? N1G C4G H4G1 109.1 . . ? C7G C4G H4G1 109.1 2_666 . ? C6G C4G H4G1 152.5 2_666 . ? C2G C4G H4G1 86.8 2_666 . ? N1G C4G H4G2 109.1 . . ? C7G C4G H4G2 109.1 2_666 . ? C6G C4G H4G2 81.7 2_666 . ? C2G C4G H4G2 149.8 2_666 . ? H4G1 C4G H4G2 107.8 . . ? N1G C5G C2G 108.7(2) . 2_666 ? N1G C5G H5G1 110.0 . . ? C2G C5G H5G1 110.0 2_666 . ? N1G C5G H5G2 110.0 . . ? C2G C5G H5G2 110.0 2_666 . ? H5G1 C5G H5G2 108.3 . . ? N1G C6G C3G 112.0(2) . 2_666 ? N1G C6G C4G 87.4(2) . 2_666 ? C3G C6G C4G 39.66(18) 2_666 2_666 ? N1G C6G H6G1 109.2 . . ? C3G C6G H6G1 109.2 2_666 . ? C4G C6G H6G1 90.1 2_666 . ? N1G C6G H6G2 109.2 . . ? C3G C6G H6G2 109.2 2_666 . ? C4G C6G H6G2 148.8 2_666 . ? H6G1 C6G H6G2 107.9 . . ? N1G C7G C4G 109.8(2) . 2_666 ? N1G C7G H7G1 109.7 . . ? C4G C7G H7G1 109.7 2_666 . ? N1G C7G H7G2 109.7 . . ? C4G C7G H7G2 109.7 2_666 . ? H7G1 C7G H7G2 108.2 . . ? 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 C6 C1 C2 C3 2.5(2) . . . . ? C13 C1 C2 C3 -172.16(12) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C5 -1.8(2) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C12 O1 C6 C5 164.76(12) . . . . ? C12 O1 C6 C1 -15.18(17) . . . . ? C4 C5 C6 O1 -177.46(13) . . . . ? C4 C5 C6 C1 2.5(2) . . . . ? C2 C1 C6 O1 176.00(11) . . . . ? C13 C1 C6 O1 -9.17(19) . . . . ? C2 C1 C6 C5 -3.9(2) . . . . ? C13 C1 C6 C5 170.90(12) . . . . ? C12 C7 C8 C9 -0.38(19) . . . . ? C13 C7 C8 C9 175.17(12) . . . . ? C7 C8 C9 C10 0.7(2) . . . . ? C8 C9 C10 C11 0.2(2) . . . . ? C9 C10 C11 C12 -1.5(2) . . . . ? C6 O1 C12 C7 18.89(17) . . . . ? C6 O1 C12 C11 -162.55(11) . . . . ? C8 C7 C12 O1 177.59(11) . . . . ? C13 C7 C12 O1 2.01(18) . . . . ? C8 C7 C12 C11 -0.89(19) . . . . ? C13 C7 C12 C11 -176.48(11) . . . . ? C10 C11 C12 O1 -176.76(12) . . . . ? C10 C11 C12 C7 1.8(2) . . . . ? C12 C7 C13 O2 94.49(13) . . . . ? C8 C7 C13 O2 -80.93(14) . . . . ? C12 C7 C13 C1 -23.48(15) . . . . ? C8 C7 C13 C1 161.10(11) . . . . ? C12 C7 C13 C14 -147.08(11) . . . . ? C8 C7 C13 C14 37.51(15) . . . . ? C6 C1 C13 O2 -91.78(13) . . . . ? C2 C1 C13 O2 82.74(14) . . . . ? C6 C1 C13 C7 26.92(15) . . . . ? C2 C1 C13 C7 -158.56(12) . . . . ? C6 C1 C13 C14 150.09(11) . . . . ? C2 C1 C13 C14 -35.39(16) . . . . ? O2 C13 C14 C19 178.79(11) . . . . ? C7 C13 C14 C19 59.22(15) . . . . ? C1 C13 C14 C19 -62.63(14) . . . . ? O2 C13 C14 C15 -0.07(15) . . . . ? C7 C13 C14 C15 -119.64(13) . . . . ? C1 C13 C14 C15 118.51(13) . . . . ? C19 C14 C15 C16 -0.07(19) . . . . ? C13 C14 C15 C16 178.82(11) . . . . ? C14 C15 C16 C17 0.1(2) . . . . ? C20 O3 C17 C18 -0.84(19) . . . . ? C20 O3 C17 C16 179.42(12) . . . . ? C15 C16 C17 O3 179.69(11) . . . . ? C15 C16 C17 C18 -0.1(2) . . . . ? O3 C17 C18 C19 -179.77(12) . . . . ? C16 C17 C18 C19 0.0(2) . . . . ? C15 C14 C19 C18 -0.04(19) . . . . ? C13 C14 C19 C18 -178.94(11) . . . . ? C17 C18 C19 C14 0.1(2) . . . . ? C7G N1G C2G C5G -82.0(3) . . . 2_666 ? C4G N1G C2G C5G 55.5(3) . . . 2_666 ? C3G N1G C2G C5G 79.2(3) . . . 2_666 ? C5G N1G C2G C5G -2.2(6) . . . 2_666 ? C6G N1G C2G C5G -59.4(3) . . . 2_666 ? C7G N1G C2G C4G -46.0(2) . . . 2_666 ? C4G N1G C2G C4G 91.6(2) . . . 2_666 ? C3G N1G C2G C4G 115.2(2) . . . 2_666 ? C5G N1G C2G C4G 33.8(4) . . . 2_666 ? C6G N1G C2G C4G -23.4(2) . . . 2_666 ? C7G N1G C3G C6G -56.1(4) . . . 2_666 ? C4G N1G C3G C6G 78.2(3) . . . 2_666 ? C5G N1G C3G C6G 65.9(3) . . . 2_666 ? C6G N1G C3G C6G 6.9(6) . . . 2_666 ? C2G N1G C3G C6G -72.2(3) . . . 2_666 ? C7G N1G C4G C7G -7.4(6) . . . 2_666 ? C3G N1G C4G C7G -86.8(3) . . . 2_666 ? C5G N1G C4G C7G 79.2(3) . . . 2_666 ? C6G N1G C4G C7G 52.7(4) . . . 2_666 ? C2G N1G C4G C7G -60.0(4) . . . 2_666 ? C7G N1G C4G C6G 32.3(4) . . . 2_666 ? C3G N1G C4G C6G -47.1(2) . . . 2_666 ? C5G N1G C4G C6G 118.8(2) . . . 2_666 ? C6G N1G C4G C6G 92.3(2) . . . 2_666 ? C2G N1G C4G C6G -20.3(2) . . . 2_666 ? C7G N1G C4G C2G -42.0(4) . . . 2_666 ? C3G N1G C4G C2G -121.4(3) . . . 2_666 ? C5G N1G C4G C2G 44.52(18) . . . 2_666 ? C6G N1G C4G C2G 18.0(2) . . . 2_666 ? C2G N1G C4G C2G -94.6(2) . . . 2_666 ? C7G N1G C5G C2G 59.8(3) . . . 2_666 ? C4G N1G C5G C2G -73.5(3) . . . 2_666 ? C3G N1G C5G C2G -62.1(3) . . . 2_666 ? C6G N1G C5G C2G 76.4(3) . . . 2_666 ? C2G N1G C5G C2G 2.2(6) . . . 2_666 ? C7G N1G C6G C3G 77.3(3) . . . 2_666 ? C4G N1G C6G C3G -57.9(4) . . . 2_666 ? C3G N1G C6G C3G -7.0(6) . . . 2_666 ? C5G N1G C6G C3G -84.1(3) . . . 2_666 ? C2G N1G C6G C3G 55.7(3) . . . 2_666 ? C7G N1G C6G C4G 45.4(2) . . . 2_666 ? C4G N1G C6G C4G -89.7(2) . . . 2_666 ? C3G N1G C6G C4G -38.9(4) . . . 2_666 ? C5G N1G C6G C4G -116.0(2) . . . 2_666 ? C2G N1G C6G C4G 23.8(2) . . . 2_666 ? C4G N1G C7G C4G 7.3(6) . . . 2_666 ? C3G N1G C7G C4G 62.4(4) . . . 2_666 ? C5G N1G C7G C4G -56.8(4) . . . 2_666 ? C6G N1G C7G C4G -73.6(3) . . . 2_666 ? C2G N1G C7G C4G 80.0(3) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.192 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.041