# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Nassimbeni, Luigi R.' 'Su, Hong' _publ_contact_author_name 'Prof Luigi R Nassimbeni' _publ_contact_author_address ; Department of Chemistry University of Cape Town Rondebosch 7701 SOUTH AFRICA ; _publ_contact_author_email 'XRAYLUIG@SCIENCE.UCT.AC.ZA' _publ_section_title ; Inclusion compounds of binaphthol with xylidines: structures, selectivity and kinetics of desolvation ; data_bnp.35x _database_code_CSD 176345 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-dihydroxy-1,1'-binaphthyl 3,5-xylidine clathrate ; _chemical_name_common bnp.35x _chemical_melting_point '410K for guest release onset temp. and 489K for host melting temp.' _chemical_formula_moiety C20H14O2.C8H11N _chemical_formula_sum 'C28 H25 N O2' _chemical_formula_weight 407.49 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 #P1bar loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.907(2) _cell_length_b 8.956(3) _cell_length_c 13.887(2) _cell_angle_alpha 98.682(17) _cell_angle_beta 98.451(13) _cell_angle_gamma 94.255(19) _cell_volume 1077.9(5) _cell_formula_units_Z 2 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.255 _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.078 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1\%, 40s per \%, 2 iterations. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 4039 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3785 _reflns_number_gt 2596 _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_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^)+(0.0611P)^2^+0.1463P] 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 SHELXL _refine_ls_extinction_coef 0.020(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3785 _refine_ls_number_parameters 299 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.23673(17) 0.18869(18) 0.82795(11) 0.0423(4) Uani 1 1 d . . . C11 C 0.28548(17) 0.09652(17) 0.74073(11) 0.0420(4) Uani 1 1 d . . . C9 C 0.29360(18) 0.34498(18) 0.85601(11) 0.0436(4) Uani 1 1 d . . . O1 O 0.08509(16) -0.02304(16) 0.86576(11) 0.0708(4) Uani 1 1 d D . . C6G C -0.03324(19) -0.47433(19) 0.73482(12) 0.0498(4) Uani 1 1 d . . . H6G H 0.0241 -0.4820 0.7952 0.060 Uiso 1 1 calc R . . C10 C 0.2506(2) 0.4327(2) 0.93980(11) 0.0512(4) Uani 1 1 d . . . C2 C 0.14214(19) 0.1246(2) 0.88361(12) 0.0499(4) Uani 1 1 d . . . C19 C 0.42454(17) 0.02721(17) 0.75192(12) 0.0435(4) Uani 1 1 d . . . C1G C 0.01319(19) -0.36449(18) 0.68193(13) 0.0487(4) Uani 1 1 d . . . C8 C 0.39420(19) 0.41620(19) 0.80353(12) 0.0509(4) Uani 1 1 d . . . H8 H 0.4230 0.3608 0.7482 0.061 Uiso 1 1 calc R . . O2 O 0.06428(16) 0.14404(19) 0.63227(10) 0.0777(5) Uani 1 1 d D . . C20 C 0.4704(2) -0.05708(18) 0.66742(14) 0.0539(5) Uani 1 1 d . . . C2G C -0.0714(2) -0.3535(2) 0.59231(13) 0.0537(4) Uani 1 1 d . . . H2G H -0.0401 -0.2801 0.5567 0.064 Uiso 1 1 calc R . . C12 C 0.19855(19) 0.0806(2) 0.64931(12) 0.0520(4) Uani 1 1 d . . . C3 C 0.0990(2) 0.2130(2) 0.96684(13) 0.0599(5) Uani 1 1 d . . . H3 H 0.0337 0.1688 1.0034 0.072 Uiso 1 1 calc R . . C5G C -0.16289(19) -0.57211(19) 0.69937(13) 0.0502(4) Uani 1 1 d . . . C15 C 0.6084(2) -0.1244(2) 0.67948(18) 0.0711(6) Uani 1 1 d . . . H15 H 0.6387 -0.1804 0.6248 0.085 Uiso 1 1 calc R . . C3G C -0.2020(2) -0.4500(2) 0.55459(12) 0.0544(4) Uani 1 1 d . . . C18 C 0.52000(19) 0.0397(2) 0.84339(14) 0.0538(4) Uani 1 1 d . . . H18 H 0.4917 0.0936 0.8995 0.065 Uiso 1 1 calc R . . C14 C 0.3752(2) -0.0698(2) 0.57554(14) 0.0643(5) Uani 1 1 d . . . H14 H 0.4041 -0.1247 0.5200 0.077 Uiso 1 1 calc R . . C13 C 0.2424(2) -0.0039(2) 0.56586(13) 0.0645(5) Uani 1 1 d . . . H13 H 0.1809 -0.0146 0.5045 0.077 Uiso 1 1 calc R . . C4G C -0.2464(2) -0.5580(2) 0.60948(13) 0.0556(5) Uani 1 1 d . . . H4G H -0.3348 -0.6228 0.5852 0.067 Uiso 1 1 calc R . . C4 C 0.1519(2) 0.3612(2) 0.99348(13) 0.0599(5) Uani 1 1 d . . . H4 H 0.1227 0.4173 1.0485 0.072 Uiso 1 1 calc R . . C5 C 0.3095(3) 0.5871(2) 0.96629(14) 0.0684(6) Uani 1 1 d . . . H5 H 0.2808 0.6458 1.0205 0.082 Uiso 1 1 calc R . . C7 C 0.4501(2) 0.5648(2) 0.83235(14) 0.0657(5) Uani 1 1 d . . . H7 H 0.5174 0.6091 0.7972 0.079 Uiso 1 1 calc R . . C6 C 0.4067(3) 0.6509(2) 0.91444(15) 0.0765(6) Uani 1 1 d . . . H6 H 0.4447 0.7523 0.9335 0.092 Uiso 1 1 calc R . . C17 C 0.6535(2) -0.0262(2) 0.85107(17) 0.0712(6) Uani 1 1 d . . . H17 H 0.7158 -0.0152 0.9121 0.085 Uiso 1 1 calc R . . C16 C 0.6982(2) -0.1097(2) 0.7686(2) 0.0803(7) Uani 1 1 d . . . H16 H 0.7890 -0.1550 0.7748 0.096 Uiso 1 1 calc R . . N1G N 0.14443(19) -0.2619(2) 0.72165(15) 0.0666(5) Uani 1 1 d D . . C8G C -0.2121(3) -0.6921(3) 0.75628(17) 0.0752(6) Uani 1 1 d . . . H8G1 H -0.2979 -0.6624 0.7866 0.113 Uiso 1 1 calc R . . H8G2 H -0.1295 -0.7039 0.8064 0.113 Uiso 1 1 calc R . . H8G3 H -0.2406 -0.7867 0.7122 0.113 Uiso 1 1 calc R . . C7G C -0.2926(3) -0.4389(3) 0.45603(15) 0.0790(6) Uani 1 1 d . . . H7G3 H -0.3393 -0.3454 0.4606 0.118 Uiso 1 1 calc R . . H7G1 H -0.3703 -0.5228 0.4371 0.118 Uiso 1 1 calc R . . H7G2 H -0.2261 -0.4415 0.4075 0.118 Uiso 1 1 calc R . . H1G1 H 0.219(2) -0.305(3) 0.7614(16) 0.095(8) Uiso 1 1 d D . . H1 H 0.117(3) -0.088(2) 0.8128(15) 0.105(8) Uiso 1 1 d D . . H1G2 H 0.191(3) -0.224(3) 0.6716(15) 0.105(9) Uiso 1 1 d D . . H2 H 0.047(3) 0.207(3) 0.6916(16) 0.137(11) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0403(8) 0.0466(9) 0.0390(8) 0.0039(7) 0.0049(7) 0.0069(7) C11 0.0433(8) 0.0388(8) 0.0426(9) 0.0014(7) 0.0106(7) -0.0011(7) C9 0.0478(9) 0.0448(9) 0.0359(8) 0.0042(7) -0.0007(7) 0.0097(7) O1 0.0780(9) 0.0591(9) 0.0770(9) 0.0022(7) 0.0358(8) -0.0101(7) C6G 0.0492(9) 0.0516(10) 0.0482(9) 0.0044(8) 0.0073(7) 0.0122(8) C10 0.0640(11) 0.0513(10) 0.0366(9) 0.0037(7) 0.0010(8) 0.0161(8) C2 0.0479(9) 0.0529(10) 0.0492(9) 0.0064(8) 0.0110(7) 0.0044(8) C19 0.0442(9) 0.0321(8) 0.0541(9) 0.0054(7) 0.0133(7) -0.0038(7) C1G 0.0463(9) 0.0414(9) 0.0575(10) -0.0006(8) 0.0136(8) 0.0057(7) C8 0.0573(10) 0.0508(10) 0.0427(9) 0.0067(7) 0.0044(8) 0.0017(8) O2 0.0630(8) 0.1079(12) 0.0558(8) -0.0014(8) -0.0050(7) 0.0265(8) C20 0.0560(10) 0.0375(9) 0.0702(12) 0.0005(8) 0.0281(9) -0.0017(8) C2G 0.0609(11) 0.0473(10) 0.0565(10) 0.0109(8) 0.0173(9) 0.0091(8) C12 0.0517(10) 0.0570(11) 0.0441(9) 0.0013(8) 0.0061(8) 0.0022(8) C3 0.0616(11) 0.0730(13) 0.0509(10) 0.0116(9) 0.0228(9) 0.0123(10) C5G 0.0510(9) 0.0443(9) 0.0571(10) 0.0064(8) 0.0154(8) 0.0076(8) C15 0.0664(13) 0.0494(11) 0.1027(17) 0.0030(11) 0.0388(13) 0.0091(9) C3G 0.0589(11) 0.0558(10) 0.0477(10) 0.0013(8) 0.0086(8) 0.0150(9) C18 0.0504(10) 0.0487(10) 0.0628(11) 0.0122(8) 0.0081(8) 0.0034(8) C14 0.0775(13) 0.0557(11) 0.0577(11) -0.0098(9) 0.0285(10) -0.0030(10) C13 0.0733(13) 0.0709(13) 0.0433(10) -0.0046(9) 0.0095(9) -0.0041(10) C4G 0.0490(10) 0.0509(10) 0.0620(11) -0.0026(8) 0.0069(8) 0.0019(8) C4 0.0742(12) 0.0649(12) 0.0430(10) 0.0021(9) 0.0161(9) 0.0224(10) C5 0.1045(16) 0.0518(12) 0.0448(10) -0.0017(9) 0.0042(10) 0.0171(11) C7 0.0827(14) 0.0537(11) 0.0564(11) 0.0120(9) 0.0019(10) -0.0084(10) C6 0.1171(18) 0.0450(11) 0.0582(12) 0.0030(9) -0.0039(12) -0.0048(11) C17 0.0555(11) 0.0657(13) 0.0944(16) 0.0256(12) 0.0041(11) 0.0103(10) C16 0.0565(12) 0.0617(13) 0.130(2) 0.0201(14) 0.0261(14) 0.0203(10) N1G 0.0560(10) 0.0558(10) 0.0823(12) 0.0019(9) 0.0079(9) -0.0060(8) C8G 0.0750(13) 0.0709(14) 0.0868(15) 0.0276(12) 0.0229(12) 0.0039(11) C7G 0.0853(15) 0.0918(16) 0.0566(12) 0.0078(11) 0.0005(11) 0.0193(13) _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 C1 C2 1.375(2) . ? C1 C9 1.428(2) . ? C1 C11 1.498(2) . ? C11 C12 1.368(2) . ? C11 C19 1.425(2) . ? C9 C8 1.410(2) . ? C9 C10 1.420(2) . ? O1 C2 1.353(2) . ? O1 H1 0.957(13) . ? C6G C5G 1.377(2) . ? C6G C1G 1.388(2) . ? C6G H6G 0.9300 . ? C10 C4 1.411(3) . ? C10 C5 1.416(3) . ? C2 C3 1.418(2) . ? C19 C18 1.405(2) . ? C19 C20 1.426(2) . ? C1G C2G 1.378(2) . ? C1G N1G 1.419(2) . ? C8 C7 1.365(3) . ? C8 H8 0.9300 . ? O2 C12 1.366(2) . ? O2 H2 0.965(17) . ? C20 C14 1.408(3) . ? C20 C15 1.409(3) . ? C2G C3G 1.382(3) . ? C2G H2G 0.9300 . ? C12 C13 1.407(2) . ? C3 C4 1.352(3) . ? C3 H3 0.9300 . ? C5G C4G 1.384(2) . ? C5G C8G 1.504(3) . ? C15 C16 1.354(3) . ? C15 H15 0.9300 . ? C3G C4G 1.389(3) . ? C3G C7G 1.504(3) . ? C18 C17 1.364(3) . ? C18 H18 0.9300 . ? C14 C13 1.359(3) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C4G H4G 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.352(3) . ? C5 H5 0.9300 . ? C7 C6 1.397(3) . ? C7 H7 0.9300 . ? C6 H6 0.9300 . ? C17 C16 1.396(3) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? N1G H1G1 0.944(16) . ? N1G H1G2 0.951(17) . ? C8G H8G1 0.9600 . ? C8G H8G2 0.9600 . ? C8G H8G3 0.9600 . ? C7G H7G3 0.9600 . ? C7G H7G1 0.9600 . ? C7G H7G2 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 119.24(15) . . ? C2 C1 C11 121.27(15) . . ? C9 C1 C11 119.45(14) . . ? C12 C11 C19 119.41(15) . . ? C12 C11 C1 120.34(14) . . ? C19 C11 C1 120.23(14) . . ? C8 C9 C10 118.12(15) . . ? C8 C9 C1 121.93(14) . . ? C10 C9 C1 119.94(15) . . ? C2 O1 H1 117.5(15) . . ? C5G C6G C1G 121.04(16) . . ? C5G C6G H6G 119.5 . . ? C1G C6G H6G 119.5 . . ? C4 C10 C5 122.97(17) . . ? C4 C10 C9 118.30(16) . . ? C5 C10 C9 118.73(17) . . ? O1 C2 C1 124.40(15) . . ? O1 C2 C3 115.09(16) . . ? C1 C2 C3 120.51(16) . . ? C18 C19 C11 122.50(15) . . ? C18 C19 C20 118.26(16) . . ? C11 C19 C20 119.23(15) . . ? C2G C1G C6G 119.50(16) . . ? C2G C1G N1G 120.58(17) . . ? C6G C1G N1G 119.90(17) . . ? C7 C8 C9 121.31(17) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C12 O2 H2 110.1(18) . . ? C14 C20 C15 122.87(18) . . ? C14 C20 C19 118.50(16) . . ? C15 C20 C19 118.63(18) . . ? C1G C2G C3G 120.91(17) . . ? C1G C2G H2G 119.5 . . ? C3G C2G H2G 119.5 . . ? O2 C12 C11 123.04(16) . . ? O2 C12 C13 115.38(16) . . ? C11 C12 C13 121.58(17) . . ? C4 C3 C2 120.48(17) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C6G C5G C4G 118.33(17) . . ? C6G C5G C8G 120.97(17) . . ? C4G C5G C8G 120.70(17) . . ? C16 C15 C20 121.7(2) . . ? C16 C15 H15 119.2 . . ? C20 C15 H15 119.2 . . ? C2G C3G C4G 118.34(16) . . ? C2G C3G C7G 120.67(18) . . ? C4G C3G C7G 120.99(18) . . ? C17 C18 C19 120.90(19) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C13 C14 C20 121.74(17) . . ? C13 C14 H14 119.1 . . ? C20 C14 H14 119.1 . . ? C14 C13 C12 119.52(18) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C5G C4G C3G 121.88(16) . . ? C5G C4G H4G 119.1 . . ? C3G C4G H4G 119.1 . . ? C3 C4 C10 121.51(16) . . ? C3 C4 H4 119.2 . . ? C10 C4 H4 119.2 . . ? C6 C5 C10 121.34(19) . . ? C6 C5 H5 119.3 . . ? C10 C5 H5 119.3 . . ? C8 C7 C6 120.35(19) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C5 C6 C7 120.14(19) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C18 C17 C16 121.0(2) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C15 C16 C17 119.56(19) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C1G N1G H1G1 112.7(15) . . ? C1G N1G H1G2 112.1(15) . . ? H1G1 N1G H1G2 108(2) . . ? C5G C8G H8G1 109.5 . . ? C5G C8G H8G2 109.5 . . ? H8G1 C8G H8G2 109.5 . . ? C5G C8G H8G3 109.5 . . ? H8G1 C8G H8G3 109.5 . . ? H8G2 C8G H8G3 109.5 . . ? C3G C7G H7G3 109.5 . . ? C3G C7G H7G1 109.5 . . ? H7G3 C7G H7G1 109.5 . . ? C3G C7G H7G2 109.5 . . ? H7G3 C7G H7G2 109.5 . . ? H7G1 C7G H7G2 109.5 . . ? 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 C2 C1 C11 C12 88.3(2) . . . . ? C9 C1 C11 C12 -93.89(18) . . . . ? C2 C1 C11 C19 -93.03(19) . . . . ? C9 C1 C11 C19 84.80(19) . . . . ? C2 C1 C9 C8 178.27(15) . . . . ? C11 C1 C9 C8 0.4(2) . . . . ? C2 C1 C9 C10 -0.8(2) . . . . ? C11 C1 C9 C10 -178.72(13) . . . . ? C8 C9 C10 C4 -178.97(15) . . . . ? C1 C9 C10 C4 0.2(2) . . . . ? C8 C9 C10 C5 0.4(2) . . . . ? C1 C9 C10 C5 179.59(15) . . . . ? C9 C1 C2 O1 -178.02(15) . . . . ? C11 C1 C2 O1 -0.2(3) . . . . ? C9 C1 C2 C3 1.2(2) . . . . ? C11 C1 C2 C3 179.06(15) . . . . ? C12 C11 C19 C18 179.54(15) . . . . ? C1 C11 C19 C18 0.8(2) . . . . ? C12 C11 C19 C20 0.1(2) . . . . ? C1 C11 C19 C20 -178.56(14) . . . . ? C5G C6G C1G C2G -0.3(2) . . . . ? C5G C6G C1G N1G 177.91(15) . . . . ? C10 C9 C8 C7 0.5(2) . . . . ? C1 C9 C8 C7 -178.66(16) . . . . ? C18 C19 C20 C14 -179.92(16) . . . . ? C11 C19 C20 C14 -0.5(2) . . . . ? C18 C19 C20 C15 0.3(2) . . . . ? C11 C19 C20 C15 179.73(15) . . . . ? C6G C1G C2G C3G 0.2(2) . . . . ? N1G C1G C2G C3G -177.96(16) . . . . ? C19 C11 C12 O2 -179.68(16) . . . . ? C1 C11 C12 O2 -1.0(3) . . . . ? C19 C11 C12 C13 0.6(3) . . . . ? C1 C11 C12 C13 179.29(16) . . . . ? O1 C2 C3 C4 178.36(17) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? C1G C6G C5G C4G -0.2(2) . . . . ? C1G C6G C5G C8G 179.36(16) . . . . ? C14 C20 C15 C16 179.64(19) . . . . ? C19 C20 C15 C16 -0.6(3) . . . . ? C1G C2G C3G C4G 0.3(3) . . . . ? C1G C2G C3G C7G -179.09(17) . . . . ? C11 C19 C18 C17 -178.94(16) . . . . ? C20 C19 C18 C17 0.5(2) . . . . ? C15 C20 C14 C13 179.90(18) . . . . ? C19 C20 C14 C13 0.1(3) . . . . ? C20 C14 C13 C12 0.6(3) . . . . ? O2 C12 C13 C14 179.29(18) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C6G C5G C4G C3G 0.7(3) . . . . ? C8G C5G C4G C3G -178.85(17) . . . . ? C2G C3G C4G C5G -0.7(3) . . . . ? C7G C3G C4G C5G 178.63(17) . . . . ? C2 C3 C4 C10 0.3(3) . . . . ? C5 C10 C4 C3 -179.28(17) . . . . ? C9 C10 C4 C3 0.1(3) . . . . ? C4 C10 C5 C6 178.41(18) . . . . ? C9 C10 C5 C6 -1.0(3) . . . . ? C9 C8 C7 C6 -0.9(3) . . . . ? C10 C5 C6 C7 0.6(3) . . . . ? C8 C7 C6 C5 0.4(3) . . . . ? C19 C18 C17 C16 -1.0(3) . . . . ? C20 C15 C16 C17 0.1(3) . . . . ? C18 C17 C16 C15 0.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1G 0.957(13) 1.909(14) 2.837(2) 163(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.031 data_bnp.2(26x) _database_code_CSD 176346 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-dihydroxy-1,1'-binaphthyl bi-2,6-xylidine clathrate ; _chemical_name_common bnp.2(26x) _chemical_melting_point '384K for guest release onset temp. and 489K for host melting temp.' _chemical_formula_moiety C20H14O2.C16H22N2 _chemical_formula_sum 'C36 H36 N2 O2' _chemical_formula_weight 528.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.066(2) _cell_length_b 10.068(2) _cell_length_c 11.868(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.11(5) _cell_angle_gamma 90.00 _cell_volume 2943.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.193 _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.073 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 50mm; combination of \f and \w scans of 1\%, 60s per \%, 2 iterations. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 5323 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2574 _reflns_number_gt 1705 _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_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^)+(0.1232P)^2^+2.1800P] 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 SHELXL _refine_ls_extinction_coef 0.0014(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2574 _refine_ls_number_parameters 188 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.2198 _refine_ls_wR_factor_gt 0.1960 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.067 _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 0.02661(7) 0.1168(2) 0.63869(18) 0.0614(6) Uani 1 1 d D . . C1 C 0.03030(9) 0.2943(2) 0.7697(2) 0.0373(6) Uani 1 1 d . . . C10 C 0.11978(10) 0.3732(3) 0.8996(2) 0.0440(6) Uani 1 1 d . . . C9 C 0.06234(10) 0.3853(2) 0.8567(2) 0.0396(6) Uani 1 1 d . . . C3 C 0.11388(10) 0.1896(3) 0.7671(2) 0.0467(7) Uani 1 1 d . . . H3 H 0.1308 0.1251 0.7355 0.056 Uiso 1 1 calc R . . C4 C 0.14417(10) 0.2725(3) 0.8533(2) 0.0476(7) Uani 1 1 d . . . H4 H 0.1817 0.2624 0.8822 0.057 Uiso 1 1 calc R . . C2 C 0.05668(10) 0.2006(2) 0.7249(2) 0.0422(6) Uani 1 1 d . . . C8 C 0.03847(11) 0.4901(3) 0.9018(2) 0.0491(7) Uani 1 1 d . . . H8 H 0.0010 0.5015 0.8735 0.059 Uiso 1 1 calc R . . C5 C 0.15051(12) 0.4620(3) 0.9884(3) 0.0579(8) Uani 1 1 d . . . H5 H 0.1881 0.4530 1.0184 0.069 Uiso 1 1 calc R . . C1G C 0.13023(11) -0.0995(3) 0.6009(2) 0.0525(8) Uani 1 1 d . . . N1G N 0.08161(11) -0.0448(3) 0.5221(3) 0.0810(10) Uani 1 1 d D . . C7 C 0.06992(13) 0.5747(3) 0.9865(3) 0.0625(9) Uani 1 1 d . . . H7 H 0.0535 0.6430 1.0151 0.075 Uiso 1 1 calc R . . C6 C 0.12607(14) 0.5602(3) 1.0307(3) 0.0685(9) Uani 1 1 d . . . H6 H 0.1469 0.6178 1.0891 0.082 Uiso 1 1 calc R . . C2G C 0.18053(13) -0.0427(3) 0.5998(3) 0.0639(9) Uani 1 1 d . . . C6G C 0.13061(16) -0.1976(3) 0.6810(3) 0.0719(10) Uani 1 1 d . . . C3G C 0.22823(13) -0.0905(4) 0.6805(4) 0.0790(11) Uani 1 1 d . . . H3G H 0.2614 -0.0544 0.6828 0.095 Uiso 1 1 calc R . . C4G C 0.22659(17) -0.1885(5) 0.7553(4) 0.0957(13) Uani 1 1 d . . . H4G H 0.2591 -0.2200 0.8082 0.115 Uiso 1 1 calc R . . C7G C 0.18284(18) 0.0631(4) 0.5152(4) 0.0943(13) Uani 1 1 d . . . H7G1 H 0.2191 0.0975 0.5369 0.141 Uiso 1 1 calc R . . H7G2 H 0.1583 0.1333 0.5178 0.141 Uiso 1 1 calc R . . H7G3 H 0.1726 0.0273 0.4360 0.141 Uiso 1 1 calc R . . C5G C 0.1792(2) -0.2440(4) 0.7572(4) 0.0945(13) Uani 1 1 d . . . H5G H 0.1797 -0.3129 0.8097 0.113 Uiso 1 1 calc R . . C8G C 0.0762(2) -0.2543(6) 0.6802(5) 0.1215(19) Uani 1 1 d . . . H8G1 H 0.0516 -0.1828 0.6790 0.182 Uiso 1 1 calc R . . H8G2 H 0.0814 -0.3071 0.7505 0.182 Uiso 1 1 calc R . . H8G3 H 0.0612 -0.3087 0.6107 0.182 Uiso 1 1 calc R . . H1 H 0.0486(14) 0.067(3) 0.602(3) 0.095(12) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0396(10) 0.0637(13) 0.0697(13) -0.0283(11) 0.0027(9) 0.0062(9) C1 0.0340(13) 0.0395(13) 0.0378(12) 0.0032(10) 0.0110(10) -0.0001(10) C10 0.0398(13) 0.0484(15) 0.0434(13) 0.0040(12) 0.0129(11) -0.0083(11) C9 0.0412(13) 0.0398(13) 0.0391(13) 0.0036(10) 0.0150(11) -0.0047(10) C3 0.0377(14) 0.0500(15) 0.0503(15) 0.0002(12) 0.0115(12) 0.0067(11) C4 0.0347(13) 0.0552(16) 0.0507(15) 0.0046(13) 0.0110(11) -0.0020(12) C2 0.0379(13) 0.0427(14) 0.0430(13) -0.0023(11) 0.0090(11) 0.0008(11) C8 0.0504(15) 0.0470(15) 0.0537(16) -0.0070(12) 0.0223(13) -0.0064(12) C5 0.0454(15) 0.0639(19) 0.0601(18) -0.0068(15) 0.0114(13) -0.0177(14) C1G 0.0437(15) 0.0563(17) 0.0532(16) -0.0228(14) 0.0101(12) 0.0051(13) N1G 0.0517(15) 0.098(2) 0.0789(19) -0.0344(17) 0.0021(13) 0.0168(15) C7 0.070(2) 0.0556(18) 0.069(2) -0.0183(15) 0.0314(17) -0.0113(15) C6 0.071(2) 0.066(2) 0.066(2) -0.0219(16) 0.0181(17) -0.0273(17) C2G 0.065(2) 0.0584(18) 0.067(2) -0.0173(15) 0.0202(16) 0.0009(15) C6G 0.088(3) 0.064(2) 0.071(2) -0.0180(17) 0.0362(19) -0.0119(18) C3G 0.0441(18) 0.086(3) 0.101(3) -0.010(2) 0.0159(18) 0.0028(17) C4G 0.067(2) 0.096(3) 0.111(3) 0.002(3) 0.012(2) 0.009(2) C7G 0.103(3) 0.086(3) 0.101(3) -0.014(2) 0.042(3) -0.020(2) C5G 0.120(4) 0.076(3) 0.082(3) 0.004(2) 0.024(3) 0.014(3) C8G 0.127(4) 0.130(4) 0.129(4) -0.036(3) 0.072(3) -0.061(3) _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 C2 1.359(3) . ? O1 H1 0.962(14) . ? C1 C2 1.373(4) . ? C1 C9 1.428(3) . ? C1 C1 1.493(4) 2_556 ? C10 C4 1.401(4) . ? C10 C5 1.414(4) . ? C10 C9 1.420(3) . ? C9 C8 1.416(4) . ? C3 C4 1.356(4) . ? C3 C2 1.413(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C8 C7 1.367(4) . ? C8 H8 0.9300 . ? C5 C6 1.358(5) . ? C5 H5 0.9300 . ? C1G C6G 1.368(5) . ? C1G N1G 1.417(4) . ? C1G C2G 1.435(4) . ? C7 C6 1.391(5) . ? C7 H7 0.9300 . ? C6 H6 0.9300 . ? C2G C3G 1.384(5) . ? C2G C7G 1.479(5) . ? C6G C5G 1.374(6) . ? C6G C8G 1.527(5) . ? C3G C4G 1.337(6) . ? C3G H3G 0.9300 . ? C4G C5G 1.364(6) . ? C4G H4G 0.9300 . ? C7G H7G1 0.9600 . ? C7G H7G2 0.9600 . ? C7G H7G3 0.9600 . ? C5G H5G 0.9300 . ? C8G H8G1 0.9600 . ? C8G H8G2 0.9600 . ? C8G H8G3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 112(2) . . ? C2 C1 C9 118.2(2) . . ? C2 C1 C1 119.4(2) . 2_556 ? C9 C1 C1 122.4(2) . 2_556 ? C4 C10 C5 122.1(3) . . ? C4 C10 C9 118.8(2) . . ? C5 C10 C9 119.1(3) . . ? C8 C9 C10 118.1(2) . . ? C8 C9 C1 121.7(2) . . ? C10 C9 C1 120.2(2) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C10 121.0(2) . . ? C3 C4 H4 119.5 . . ? C10 C4 H4 119.5 . . ? O1 C2 C1 118.7(2) . . ? O1 C2 C3 120.0(2) . . ? C1 C2 C3 121.4(2) . . ? C7 C8 C9 120.7(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C6 C5 C10 121.0(3) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C6G C1G N1G 122.7(3) . . ? C6G C1G C2G 119.7(3) . . ? N1G C1G C2G 117.5(3) . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C3G C2G C1G 118.1(3) . . ? C3G C2G C7G 119.6(3) . . ? C1G C2G C7G 122.3(3) . . ? C1G C6G C5G 119.9(4) . . ? C1G C6G C8G 118.0(4) . . ? C5G C6G C8G 122.1(4) . . ? C4G C3G C2G 120.0(4) . . ? C4G C3G H3G 120.0 . . ? C2G C3G H3G 120.0 . . ? C3G C4G C5G 122.7(4) . . ? C3G C4G H4G 118.7 . . ? C5G C4G H4G 118.7 . . ? C2G C7G H7G1 109.5 . . ? C2G C7G H7G2 109.5 . . ? H7G1 C7G H7G2 109.5 . . ? C2G C7G H7G3 109.5 . . ? H7G1 C7G H7G3 109.5 . . ? H7G2 C7G H7G3 109.5 . . ? C4G C5G C6G 119.6(4) . . ? C4G C5G H5G 120.2 . . ? C6G C5G H5G 120.2 . . ? C6G C8G H8G1 109.5 . . ? C6G C8G H8G2 109.5 . . ? H8G1 C8G H8G2 109.5 . . ? C6G C8G H8G3 109.5 . . ? H8G1 C8G H8G3 109.5 . . ? H8G2 C8G H8G3 109.5 . . ? 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 C4 C10 C9 C8 -178.1(2) . . . . ? C5 C10 C9 C8 2.6(4) . . . . ? C4 C10 C9 C1 1.2(4) . . . . ? C5 C10 C9 C1 -178.1(2) . . . . ? C2 C1 C9 C8 175.9(2) . . . . ? C1 C1 C9 C8 -6.7(4) 2_556 . . . ? C2 C1 C9 C10 -3.4(3) . . . . ? C1 C1 C9 C10 174.0(2) 2_556 . . . ? C2 C3 C4 C10 -2.1(4) . . . . ? C5 C10 C4 C3 -179.2(3) . . . . ? C9 C10 C4 C3 1.5(4) . . . . ? C9 C1 C2 O1 -177.5(2) . . . . ? C1 C1 C2 O1 5.0(4) 2_556 . . . ? C9 C1 C2 C3 2.9(4) . . . . ? C1 C1 C2 C3 -174.6(2) 2_556 . . . ? C4 C3 C2 O1 -179.8(2) . . . . ? C4 C3 C2 C1 -0.2(4) . . . . ? C10 C9 C8 C7 -1.7(4) . . . . ? C1 C9 C8 C7 178.9(2) . . . . ? C4 C10 C5 C6 179.0(3) . . . . ? C9 C10 C5 C6 -1.8(4) . . . . ? C9 C8 C7 C6 0.0(5) . . . . ? C10 C5 C6 C7 0.0(5) . . . . ? C8 C7 C6 C5 0.9(5) . . . . ? C6G C1G C2G C3G 0.3(4) . . . . ? N1G C1G C2G C3G 176.7(3) . . . . ? C6G C1G C2G C7G 179.8(3) . . . . ? N1G C1G C2G C7G -3.8(4) . . . . ? N1G C1G C6G C5G -178.3(3) . . . . ? C2G C1G C6G C5G -2.1(5) . . . . ? N1G C1G C6G C8G 3.1(5) . . . . ? C2G C1G C6G C8G 179.3(3) . . . . ? C1G C2G C3G C4G 1.1(5) . . . . ? C7G C2G C3G C4G -178.3(4) . . . . ? C2G C3G C4G C5G -0.8(7) . . . . ? C3G C4G C5G C6G -0.9(7) . . . . ? C1G C6G C5G C4G 2.4(6) . . . . ? C8G C6G C5G C4G -179.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1G 0.962(14) 1.859(14) 2.814(3) 171(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.602 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.049 data_bnp.3(23x) _database_code_CSD 176347 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-dihydroxy-1,1'-binaphthyl tri-2,3-xylidine clathrate ; _chemical_name_common bnp.3(23x) _chemical_melting_point '489K for guest release onset temp. and 489K for host melting temp.' _chemical_formula_moiety 'C20H14O2.C24H33N3' _chemical_formula_sum 'C44 H47 N3 O2' _chemical_formula_weight 649.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 22.6340(10) _cell_length_b 10.4640(10) _cell_length_c 30.6890(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7268.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.188 _exptl_crystal_F_000 2784 _exptl_absorpt_coefficient_mu 0.073 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 55mm; combination of \f and \w scans of 1\%, 60s per \%, 2 iterations. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 24296 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0964 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 24.66 _reflns_number_total 5922 _reflns_number_gt 2847 _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_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^)+(0.1520P)^2^+7.4380P] 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 SHELXL _refine_ls_extinction_coef 0.0012(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5922 _refine_ls_number_parameters 447 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1879 _refine_ls_R_factor_gt 0.0926 _refine_ls_wR_factor_ref 0.3103 _refine_ls_wR_factor_gt 0.2539 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.023 _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 0.18163(14) 0.7014(3) 0.17916(10) 0.0455(9) Uani 1 1 d D . . C1 C 0.11252(18) 0.8691(4) 0.17805(13) 0.0291(11) Uani 1 1 d . . . O2 O 0.18533(14) 1.0353(3) 0.13188(10) 0.0436(9) Uani 1 1 d D . . C9 C 0.07544(19) 0.9566(4) 0.20136(14) 0.0319(11) Uani 1 1 d . . . C11 C 0.11474(18) 0.8695(4) 0.12964(13) 0.0297(11) Uani 1 1 d . . . C20 C 0.0837(2) 0.7822(4) 0.05842(14) 0.0344(11) Uani 1 1 d . . . C10 C 0.07388(19) 0.9542(4) 0.24751(14) 0.0351(11) Uani 1 1 d . . . C4 C 0.11038(19) 0.8644(4) 0.26988(14) 0.0348(12) Uani 1 1 d . . . H4 H 0.1101 0.8623 0.3008 0.042 Uiso 1 1 calc R . . C8 C 0.0393(2) 1.0469(4) 0.17984(15) 0.0415(12) Uani 1 1 d . . . H8 H 0.0391 1.0500 0.1489 0.050 Uiso 1 1 calc R . . C14 C 0.1225(2) 0.8690(4) 0.03789(14) 0.0360(12) Uani 1 1 d . . . H14 H 0.1258 0.8694 0.0070 0.043 Uiso 1 1 calc R . . C12 C 0.1518(2) 0.9530(4) 0.10820(14) 0.0340(11) Uani 1 1 d . . . C19 C 0.07858(19) 0.7849(4) 0.10479(14) 0.0329(11) Uani 1 1 d . . . C2 C 0.14674(19) 0.7845(4) 0.20160(14) 0.0328(11) Uani 1 1 d . . . C3 C 0.1456(2) 0.7818(4) 0.24769(14) 0.0361(12) Uani 1 1 d . . . H3 H 0.1694 0.7223 0.2631 0.043 Uiso 1 1 calc R . . C13 C 0.1550(2) 0.9518(4) 0.06193(14) 0.0371(12) Uani 1 1 d . . . H13 H 0.1805 1.0103 0.0475 0.045 Uiso 1 1 calc R . . C5 C 0.0373(2) 1.0410(5) 0.26995(16) 0.0477(14) Uani 1 1 d . . . H5 H 0.0361 1.0392 0.3009 0.057 Uiso 1 1 calc R . . C15 C 0.0483(2) 0.6958(5) 0.03450(15) 0.0435(13) Uani 1 1 d . . . H15 H 0.0519 0.6928 0.0037 0.052 Uiso 1 1 calc R . . C18 C 0.0372(2) 0.7026(5) 0.12449(16) 0.0484(14) Uani 1 1 d . . . H18 H 0.0330 0.7028 0.1553 0.058 Uiso 1 1 calc R . . N1GA N 0.2342(2) 1.0610(4) 0.22376(13) 0.0489(12) Uani 1 1 d D . . C7 C 0.0047(2) 1.1295(5) 0.20268(15) 0.0513(14) Uani 1 1 d . . . H7 H -0.0191 1.1898 0.1876 0.062 Uiso 1 1 calc R . . C17 C 0.0032(3) 0.6234(5) 0.10025(17) 0.0606(16) Uani 1 1 d . . . H17 H -0.0251 0.5709 0.1144 0.073 Uiso 1 1 calc R . . C6 C 0.0040(2) 1.1262(5) 0.24824(17) 0.0576(15) Uani 1 1 d . . . H6 H -0.0201 1.1845 0.2639 0.069 Uiso 1 1 calc R . . C16 C 0.0089(2) 0.6167(5) 0.05467(16) 0.0544(15) Uani 1 1 d . . . H16 H -0.0142 0.5582 0.0382 0.065 Uiso 1 1 calc R . . C1GA C 0.2079(2) 1.1167(5) 0.26091(16) 0.0499(14) Uani 1 1 d . . . C6GA C 0.2180(3) 1.0627(6) 0.30200(17) 0.0622(16) Uani 1 1 d . . . H6GA H 0.2426 0.9897 0.3049 0.075 Uiso 1 1 calc R . . C2GA C 0.1732(2) 1.2257(5) 0.2566(2) 0.0587(15) Uani 1 1 d . . . C7GA C 0.1628(3) 1.2797(6) 0.2109(2) 0.0766(19) Uani 1 1 d . . . H7A2 H 0.2002 1.2802 0.1948 0.115 Uiso 1 1 calc R . . H7A1 H 0.1477 1.3671 0.2132 0.115 Uiso 1 1 calc R . . H7A3 H 0.1340 1.2263 0.1955 0.115 Uiso 1 1 calc R . . C4GA C 0.1562(3) 1.2217(9) 0.3334(3) 0.092(2) Uani 1 1 d . . . H4GA H 0.1374 1.2560 0.3585 0.111 Uiso 1 1 calc R . . C5GA C 0.1919(3) 1.1163(8) 0.3380(2) 0.085(2) Uani 1 1 d . . . H5GA H 0.1985 1.0805 0.3661 0.102 Uiso 1 1 calc R . . C3GA C 0.1467(3) 1.2792(7) 0.2938(3) 0.0749(19) Uani 1 1 d . . . C8GA C 0.1068(3) 1.3918(8) 0.2911(3) 0.122(3) Uani 1 1 d . . . H8A3 H 0.0778 1.3783 0.2679 0.183 Uiso 1 1 calc R . . H8A1 H 0.1300 1.4685 0.2848 0.183 Uiso 1 1 calc R . . H8A2 H 0.0862 1.4027 0.3190 0.183 Uiso 1 1 calc R . . N1GB N 0.2244(2) 0.6540(4) 0.08863(14) 0.0557(12) Uani 1 1 d D . . C1GB C 0.19065(15) 0.5391(3) 0.07001(11) 0.084(2) Uani 1 1 d GD . . C2GB C 0.18805(12) 0.5204(3) 0.02521(11) 0.107(3) Uani 1 1 d G . . C3GB C 0.16045(17) 0.4124(4) 0.00843(11) 0.0692(19) Uani 1 1 d G . . C4GB C 0.13546(19) 0.3231(3) 0.03646(15) 0.089(2) Uani 1 1 d G . . C5GB C 0.13807(18) 0.3419(4) 0.08126(14) 0.106(3) Uani 1 1 d G . . C6GB C 0.16566(18) 0.4499(4) 0.09803(10) 0.0549(14) Uani 1 1 d G . . H6GB H 0.1674 0.4627 0.1286 0.066 Uiso 1 1 d G . . H5GB H 0.1210 0.2809 0.1004 0.066 Uiso 1 1 d G . . H4GB H 0.1166 0.2494 0.0250 0.066 Uiso 1 1 d G . . C7GB C 0.2162(2) 0.6218(4) -0.00501(16) 0.094(3) Uani 1 1 d G . . H7B1 H 0.2020 0.7069 0.0032 0.141 Uiso 1 1 calc R . . H7B2 H 0.2052 0.6039 -0.0353 0.141 Uiso 1 1 calc R . . H7B3 H 0.2593 0.6188 -0.0021 0.141 Uiso 1 1 calc R . . C8GB C 0.1592(4) 0.3929(9) -0.0401(2) 0.118(3) Uani 1 1 d . . . H8B1 H 0.1404 0.4667 -0.0540 0.177 Uiso 1 1 calc R . . H8B2 H 0.1368 0.3154 -0.0469 0.177 Uiso 1 1 calc R . . H8B3 H 0.1997 0.3841 -0.0510 0.177 Uiso 1 1 calc R . . N1GC N 0.1824(3) 0.7667(6) 0.37785(19) 0.103(2) Uani 1 1 d D . . C1GC C 0.12677(17) 0.7275(4) 0.39415(12) 0.0729(18) Uani 1 1 d GD . . C2GC C 0.11821(16) 0.6054(3) 0.41086(12) 0.080(2) Uani 1 1 d G . . C3GC C 0.06309(18) 0.5699(3) 0.42676(10) 0.0745(19) Uani 1 1 d G . . C4GC C 0.01654(16) 0.6565(4) 0.42595(12) 0.102(3) Uani 1 1 d G . . C5GC C 0.02510(19) 0.7786(4) 0.40923(13) 0.079(2) Uani 1 1 d G . . C6GC C 0.0802(2) 0.8141(3) 0.39334(12) 0.0694(17) Uani 1 1 d G . . H4GC H -0.0211 0.6323 0.4368 0.083 Uiso 1 1 d G . . H5GC H -0.0067 0.8378 0.4087 0.083 Uiso 1 1 d G . . H6GC H 0.0861 0.8975 0.3819 0.083 Uiso 1 1 d G . . C8GC C 0.0551(3) 0.4433(4) 0.44513(16) 0.103(3) Uani 1 1 d G . . H8C1 H 0.0201 0.4034 0.4322 0.155 Uiso 1 1 calc R . . H8C2 H 0.0499 0.4501 0.4768 0.155 Uiso 1 1 calc R . . H8C3 H 0.0900 0.3909 0.4388 0.155 Uiso 1 1 calc R . . H1A1 H 0.2089(18) 1.051(5) 0.1986(8) 0.069(17) Uiso 1 1 d D . . H1A2 H 0.242(2) 0.975(3) 0.2339(16) 0.073(19) Uiso 1 1 d D . . H2 H 0.2113(14) 1.088(4) 0.1146(12) 0.051(14) Uiso 1 1 d D . . H1 H 0.2082(18) 0.659(5) 0.1995(13) 0.080(19) Uiso 1 1 d D . . C7GC C 0.1708(4) 0.5185(7) 0.4117(3) 0.116(3) Uani 1 1 d . . . H7C1 H 0.1596 0.4365 0.4247 0.174 Uiso 1 1 calc R . . H7C2 H 0.2023 0.5577 0.4290 0.174 Uiso 1 1 calc R . . H7C3 H 0.1849 0.5045 0.3819 0.174 Uiso 1 1 calc R . . H1B1 H 0.199(2) 0.667(4) 0.1134(8) 0.139 Uiso 1 1 d D . . H1C1 H 0.1733(16) 0.842(4) 0.3603(19) 0.139 Uiso 1 1 d D . . H1C2 H 0.2092(17) 0.707(3) 0.3633(19) 0.139 Uiso 1 1 d D . . H1B2 H 0.232(3) 0.732(3) 0.0739(11) 0.139 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.052(2) 0.052(2) 0.0325(18) -0.0047(17) -0.0005(16) 0.0213(18) C1 0.032(3) 0.029(2) 0.026(2) -0.002(2) 0.001(2) -0.002(2) O2 0.049(2) 0.046(2) 0.0355(19) -0.0020(16) -0.0003(16) -0.0161(17) C9 0.031(3) 0.036(3) 0.029(3) 0.003(2) 0.002(2) -0.002(2) C11 0.032(3) 0.034(3) 0.023(2) 0.001(2) -0.002(2) 0.002(2) C20 0.038(3) 0.037(3) 0.029(3) 0.001(2) -0.007(2) 0.006(2) C10 0.035(3) 0.040(3) 0.030(3) -0.005(2) 0.000(2) -0.003(2) C4 0.038(3) 0.041(3) 0.025(2) -0.001(2) 0.002(2) -0.004(2) C8 0.050(3) 0.048(3) 0.027(2) 0.005(2) 0.000(2) 0.009(3) C14 0.039(3) 0.044(3) 0.025(2) 0.001(2) -0.002(2) 0.006(2) C12 0.039(3) 0.036(3) 0.027(2) -0.003(2) 0.000(2) 0.000(2) C19 0.035(3) 0.032(3) 0.031(3) 0.003(2) -0.001(2) -0.001(2) C2 0.034(3) 0.031(3) 0.033(3) -0.002(2) 0.002(2) 0.001(2) C3 0.039(3) 0.038(3) 0.031(3) 0.003(2) -0.004(2) 0.001(2) C13 0.040(3) 0.041(3) 0.030(3) 0.008(2) 0.001(2) -0.001(2) C5 0.050(3) 0.060(4) 0.033(3) -0.005(3) 0.002(2) 0.015(3) C15 0.054(3) 0.045(3) 0.031(3) -0.007(3) -0.005(2) 0.005(3) C18 0.063(4) 0.048(3) 0.033(3) -0.003(3) 0.000(3) -0.012(3) N1GA 0.061(3) 0.047(3) 0.039(3) -0.004(2) 0.006(2) -0.016(2) C7 0.061(4) 0.053(3) 0.040(3) 0.002(3) 0.000(3) 0.023(3) C17 0.070(4) 0.060(4) 0.052(4) -0.005(3) 0.004(3) -0.025(3) C6 0.063(4) 0.064(4) 0.046(3) -0.011(3) 0.004(3) 0.028(3) C16 0.065(4) 0.056(3) 0.042(3) -0.011(3) -0.007(3) -0.018(3) C1GA 0.049(3) 0.056(4) 0.045(3) -0.010(3) 0.006(3) -0.021(3) C6GA 0.062(4) 0.080(4) 0.044(3) 0.007(3) -0.002(3) -0.026(3) C2GA 0.051(3) 0.055(4) 0.070(4) -0.005(3) -0.005(3) -0.009(3) C7GA 0.074(4) 0.055(4) 0.100(5) -0.004(4) -0.013(4) -0.002(3) C4GA 0.069(5) 0.128(7) 0.079(6) -0.046(5) 0.013(4) -0.024(5) C5GA 0.082(5) 0.130(7) 0.043(4) -0.018(4) 0.009(4) -0.045(5) C3GA 0.054(4) 0.092(5) 0.079(5) -0.036(4) 0.001(4) -0.009(4) C8GA 0.084(5) 0.118(6) 0.165(8) -0.057(6) 0.006(5) 0.024(5) N1GB 0.064(3) 0.055(3) 0.048(3) -0.008(2) -0.008(2) 0.016(2) C1GB 0.059(4) 0.135(7) 0.057(4) 0.003(4) 0.005(3) 0.064(4) C2GB 0.069(5) 0.146(8) 0.106(6) 0.017(6) 0.007(4) 0.068(5) C3GB 0.046(4) 0.062(4) 0.099(5) -0.035(4) -0.023(3) -0.003(3) C4GB 0.101(6) 0.082(5) 0.085(5) 0.009(4) 0.023(4) 0.004(4) C5GB 0.109(6) 0.112(7) 0.096(6) 0.030(5) 0.021(5) -0.009(5) C6GB 0.061(4) 0.054(3) 0.050(3) 0.008(3) 0.006(3) -0.004(3) C7GB 0.059(4) 0.084(5) 0.138(6) 0.083(5) 0.057(4) 0.037(3) C8GB 0.100(6) 0.170(8) 0.083(5) 0.016(6) 0.002(5) 0.011(6) N1GC 0.101(5) 0.115(5) 0.095(5) 0.010(4) 0.010(4) 0.027(4) C1GC 0.078(5) 0.084(5) 0.057(4) -0.017(4) -0.013(3) 0.003(4) C2GC 0.108(6) 0.065(4) 0.068(4) -0.019(4) -0.043(4) 0.018(4) C3GC 0.086(5) 0.078(5) 0.059(4) -0.013(4) -0.028(4) -0.021(4) C4GC 0.115(6) 0.113(7) 0.078(5) -0.047(5) -0.052(5) 0.032(5) C5GC 0.104(6) 0.063(5) 0.069(4) -0.007(4) -0.016(4) 0.010(4) C6GC 0.082(5) 0.068(4) 0.058(4) -0.009(3) -0.017(3) 0.016(4) C8GC 0.148(7) 0.057(4) 0.104(6) 0.016(4) -0.057(5) -0.038(4) C7GC 0.115(7) 0.087(5) 0.146(7) -0.019(5) -0.052(5) 0.029(5) _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 C2 1.362(5) . ? O1 H1 0.972(16) . ? C1 C2 1.381(6) . ? C1 C9 1.433(6) . ? C1 C11 1.486(6) . ? O2 C12 1.358(5) . ? O2 H2 0.963(15) . ? C9 C8 1.414(6) . ? C9 C10 1.417(6) . ? C11 C12 1.379(6) . ? C11 C19 1.427(6) . ? C20 C14 1.412(6) . ? C20 C15 1.413(6) . ? C20 C19 1.428(6) . ? C10 C5 1.409(6) . ? C10 C4 1.428(6) . ? C4 C3 1.358(6) . ? C4 H4 0.9500 . ? C8 C7 1.360(6) . ? C8 H8 0.9500 . ? C14 C13 1.356(6) . ? C14 H14 0.9500 . ? C12 C13 1.422(6) . ? C19 C18 1.409(6) . ? C2 C3 1.415(6) . ? C3 H3 0.9500 . ? C13 H13 0.9500 . ? C5 C6 1.343(7) . ? C5 H5 0.9500 . ? C15 C16 1.364(7) . ? C15 H15 0.9500 . ? C18 C17 1.353(7) . ? C18 H18 0.9500 . ? N1GA C1GA 1.412(6) . ? N1GA H1A1 0.968(16) . ? N1GA H1A2 0.966(19) . ? C7 C6 1.398(7) . ? C7 H7 0.9500 . ? C17 C16 1.406(7) . ? C17 H17 0.9500 . ? C6 H6 0.9500 . ? C16 H16 0.9500 . ? C1GA C2GA 1.392(8) . ? C1GA C6GA 1.400(7) . ? C6GA C5GA 1.373(8) . ? C6GA H6GA 0.9500 . ? C2GA C3GA 1.406(8) . ? C2GA C7GA 1.529(8) . ? C7GA H7A2 0.9800 . ? C7GA H7A1 0.9800 . ? C7GA H7A3 0.9800 . ? C4GA C3GA 1.373(10) . ? C4GA C5GA 1.375(10) . ? C4GA H4GA 0.9500 . ? C5GA H5GA 0.9500 . ? C3GA C8GA 1.487(10) . ? C8GA H8A3 0.9800 . ? C8GA H8A1 0.9800 . ? C8GA H8A2 0.9800 . ? N1GB C1GB 1.534(6) . ? N1GB H1B1 0.958(18) . ? N1GB H1B2 0.947(18) . ? C1GB C2GB 1.3900 . ? C1GB C6GB 1.3900 . ? C2GB C3GB 1.3900 . ? C2GB C7GB 1.5464 . ? C3GB C4GB 1.3900 . ? C3GB C8GB 1.503(8) . ? C4GB C5GB 1.3900 . ? C4GB H4GB 0.9499 . ? C5GB C6GB 1.3900 . ? C5GB H5GB 0.9499 . ? C6GB H6GB 0.9499 . ? C7GB H7B1 0.9800 . ? C7GB H7B2 0.9800 . ? C7GB H7B3 0.9800 . ? C8GB H8B1 0.9800 . ? C8GB H8B2 0.9800 . ? C8GB H8B3 0.9800 . ? N1GC C1GC 1.416(7) . ? N1GC H1C1 0.974(19) . ? N1GC H1C2 0.981(18) . ? C1GC C2GC 1.3900 . ? C1GC C6GC 1.3900 . ? C2GC C3GC 1.3900 . ? C2GC C7GC 1.498(8) . ? C3GC C4GC 1.3900 . ? C3GC C8GC 1.4514 . ? C4GC C5GC 1.3900 . ? C4GC H4GC 0.9503 . ? C5GC C6GC 1.3900 . ? C5GC H5GC 0.9500 . ? C6GC H6GC 0.9500 . ? C8GC H8C1 0.9800 . ? C8GC H8C2 0.9800 . ? C8GC H8C3 0.9800 . ? C7GC H7C1 0.9800 . ? C7GC H7C2 0.9800 . ? C7GC H7C3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 109(3) . . ? C2 C1 C9 118.5(4) . . ? C2 C1 C11 120.4(4) . . ? C9 C1 C11 121.1(4) . . ? C12 O2 H2 114(3) . . ? C8 C9 C10 117.6(4) . . ? C8 C9 C1 122.2(4) . . ? C10 C9 C1 120.1(4) . . ? C12 C11 C19 119.2(4) . . ? C12 C11 C1 119.9(4) . . ? C19 C11 C1 120.9(4) . . ? C14 C20 C15 122.2(4) . . ? C14 C20 C19 118.8(4) . . ? C15 C20 C19 119.0(4) . . ? C5 C10 C9 119.5(4) . . ? C5 C10 C4 122.0(4) . . ? C9 C10 C4 118.6(4) . . ? C3 C4 C10 121.1(4) . . ? C3 C4 H4 119.4 . . ? C10 C4 H4 119.4 . . ? C7 C8 C9 121.1(4) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C13 C14 C20 120.4(4) . . ? C13 C14 H14 119.8 . . ? C20 C14 H14 119.8 . . ? O2 C12 C11 119.1(4) . . ? O2 C12 C13 120.8(4) . . ? C11 C12 C13 120.1(4) . . ? C18 C19 C11 122.1(4) . . ? C18 C19 C20 118.0(4) . . ? C11 C19 C20 119.9(4) . . ? O1 C2 C1 118.0(4) . . ? O1 C2 C3 120.3(4) . . ? C1 C2 C3 121.7(4) . . ? C4 C3 C2 120.0(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C14 C13 C12 121.5(4) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C6 C5 C10 121.0(4) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C16 C15 C20 121.5(4) . . ? C16 C15 H15 119.2 . . ? C20 C15 H15 119.2 . . ? C17 C18 C19 121.1(5) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C1GA N1GA H1A1 116(3) . . ? C1GA N1GA H1A2 102(3) . . ? H1A1 N1GA H1A2 106(5) . . ? C8 C7 C6 120.4(5) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C18 C17 C16 121.7(5) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C5 C6 C7 120.4(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C15 C16 C17 118.7(5) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C2GA C1GA C6GA 120.6(5) . . ? C2GA C1GA N1GA 120.0(5) . . ? C6GA C1GA N1GA 119.5(5) . . ? C5GA C6GA C1GA 119.3(6) . . ? C5GA C6GA H6GA 120.3 . . ? C1GA C6GA H6GA 120.3 . . ? C1GA C2GA C3GA 119.4(6) . . ? C1GA C2GA C7GA 118.5(5) . . ? C3GA C2GA C7GA 122.1(6) . . ? C2GA C7GA H7A2 109.5 . . ? C2GA C7GA H7A1 109.5 . . ? H7A2 C7GA H7A1 109.5 . . ? C2GA C7GA H7A3 109.5 . . ? H7A2 C7GA H7A3 109.5 . . ? H7A1 C7GA H7A3 109.5 . . ? C3GA C4GA C5GA 122.3(7) . . ? C3GA C4GA H4GA 118.9 . . ? C5GA C4GA H4GA 118.9 . . ? C6GA C5GA C4GA 119.9(7) . . ? C6GA C5GA H5GA 120.1 . . ? C4GA C5GA H5GA 120.1 . . ? C4GA C3GA C2GA 118.5(7) . . ? C4GA C3GA C8GA 119.4(7) . . ? C2GA C3GA C8GA 122.0(7) . . ? C3GA C8GA H8A3 109.5 . . ? C3GA C8GA H8A1 109.5 . . ? H8A3 C8GA H8A1 109.5 . . ? C3GA C8GA H8A2 109.5 . . ? H8A3 C8GA H8A2 109.5 . . ? H8A1 C8GA H8A2 109.5 . . ? C1GB N1GB H1B1 96.2(17) . . ? C1GB N1GB H1B2 126(2) . . ? H1B1 N1GB H1B2 111(3) . . ? C2GB C1GB C6GB 120.0 . . ? C2GB C1GB N1GB 120.0(3) . . ? C6GB C1GB N1GB 119.9(3) . . ? C3GB C2GB C1GB 120.0 . . ? C3GB C2GB C7GB 121.4 . . ? C1GB C2GB C7GB 118.6 . . ? C2GB C3GB C4GB 120.0 . . ? C2GB C3GB C8GB 119.0(4) . . ? C4GB C3GB C8GB 121.0(4) . . ? C3GB C4GB C5GB 120.0 . . ? C3GB C4GB H4GB 120.0 . . ? C5GB C4GB H4GB 120.0 . . ? C6GB C5GB C4GB 120.0 . . ? C6GB C5GB H5GB 120.0 . . ? C4GB C5GB H5GB 120.0 . . ? C5GB C6GB C1GB 120.0 . . ? C5GB C6GB H6GB 120.0 . . ? C1GB C6GB H6GB 120.0 . . ? C2GB C7GB H7B1 109.5 . . ? C2GB C7GB H7B2 109.5 . . ? H7B1 C7GB H7B2 109.5 . . ? C2GB C7GB H7B3 109.5 . . ? H7B1 C7GB H7B3 109.5 . . ? H7B2 C7GB H7B3 109.5 . . ? C3GB C8GB H8B1 109.5 . . ? C3GB C8GB H8B2 109.5 . . ? H8B1 C8GB H8B2 109.5 . . ? C3GB C8GB H8B3 109.5 . . ? H8B1 C8GB H8B3 109.5 . . ? H8B2 C8GB H8B3 109.5 . . ? C1GC N1GC H1C1 104.0(19) . . ? C1GC N1GC H1C2 122(2) . . ? H1C1 N1GC H1C2 113(3) . . ? C2GC C1GC C6GC 120.0 . . ? C2GC C1GC N1GC 121.4(4) . . ? C6GC C1GC N1GC 118.6(4) . . ? C1GC C2GC C3GC 120.0 . . ? C1GC C2GC C7GC 116.9(4) . . ? C3GC C2GC C7GC 123.0(4) . . ? C4GC C3GC C2GC 120.0 . . ? C4GC C3GC C8GC 120.5 . . ? C2GC C3GC C8GC 119.5 . . ? C3GC C4GC C5GC 120.0 . . ? C3GC C4GC H4GC 120.0 . . ? C5GC C4GC H4GC 120.0 . . ? C6GC C5GC C4GC 120.0 . . ? C6GC C5GC H5GC 120.0 . . ? C4GC C5GC H5GC 120.0 . . ? C5GC C6GC C1GC 120.0 . . ? C5GC C6GC H6GC 120.0 . . ? C1GC C6GC H6GC 120.0 . . ? C3GC C8GC H8C1 109.5 . . ? C3GC C8GC H8C2 109.5 . . ? H8C1 C8GC H8C2 109.5 . . ? C3GC C8GC H8C3 109.5 . . ? H8C1 C8GC H8C3 109.5 . . ? H8C2 C8GC H8C3 109.5 . . ? C2GC C7GC H7C1 109.5 . . ? C2GC C7GC H7C2 109.5 . . ? H7C1 C7GC H7C2 109.5 . . ? C2GC C7GC H7C3 109.5 . . ? H7C1 C7GC H7C3 109.5 . . ? H7C2 C7GC H7C3 109.5 . . ? 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 C2 C1 C9 C8 179.6(4) . . . . ? C11 C1 C9 C8 0.1(6) . . . . ? C2 C1 C9 C10 -0.7(6) . . . . ? C11 C1 C9 C10 179.8(4) . . . . ? C2 C1 C11 C12 -94.8(5) . . . . ? C9 C1 C11 C12 84.7(5) . . . . ? C2 C1 C11 C19 85.7(5) . . . . ? C9 C1 C11 C19 -94.8(5) . . . . ? C8 C9 C10 C5 -0.4(6) . . . . ? C1 C9 C10 C5 179.9(4) . . . . ? C8 C9 C10 C4 -179.5(4) . . . . ? C1 C9 C10 C4 0.8(6) . . . . ? C5 C10 C4 C3 -179.7(4) . . . . ? C9 C10 C4 C3 -0.6(6) . . . . ? C10 C9 C8 C7 0.7(7) . . . . ? C1 C9 C8 C7 -179.6(4) . . . . ? C15 C20 C14 C13 178.9(4) . . . . ? C19 C20 C14 C13 1.2(6) . . . . ? C19 C11 C12 O2 178.6(4) . . . . ? C1 C11 C12 O2 -0.9(6) . . . . ? C19 C11 C12 C13 -1.7(6) . . . . ? C1 C11 C12 C13 178.7(4) . . . . ? C12 C11 C19 C18 -176.1(4) . . . . ? C1 C11 C19 C18 3.4(6) . . . . ? C12 C11 C19 C20 3.7(6) . . . . ? C1 C11 C19 C20 -176.7(4) . . . . ? C14 C20 C19 C18 176.4(4) . . . . ? C15 C20 C19 C18 -1.4(6) . . . . ? C14 C20 C19 C11 -3.4(6) . . . . ? C15 C20 C19 C11 178.7(4) . . . . ? C9 C1 C2 O1 179.7(4) . . . . ? C11 C1 C2 O1 -0.8(6) . . . . ? C9 C1 C2 C3 0.5(6) . . . . ? C11 C1 C2 C3 -180.0(4) . . . . ? C10 C4 C3 C2 0.4(6) . . . . ? O1 C2 C3 C4 -179.6(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C20 C14 C13 C12 0.8(7) . . . . ? O2 C12 C13 C14 179.1(4) . . . . ? C11 C12 C13 C14 -0.5(7) . . . . ? C9 C10 C5 C6 -0.2(7) . . . . ? C4 C10 C5 C6 178.9(5) . . . . ? C14 C20 C15 C16 -176.8(5) . . . . ? C19 C20 C15 C16 0.9(7) . . . . ? C11 C19 C18 C17 179.9(5) . . . . ? C20 C19 C18 C17 0.0(7) . . . . ? C9 C8 C7 C6 -0.3(8) . . . . ? C19 C18 C17 C16 1.9(9) . . . . ? C10 C5 C6 C7 0.6(8) . . . . ? C8 C7 C6 C5 -0.3(9) . . . . ? C20 C15 C16 C17 1.0(8) . . . . ? C18 C17 C16 C15 -2.4(9) . . . . ? C2GA C1GA C6GA C5GA 1.8(8) . . . . ? N1GA C1GA C6GA C5GA -179.3(5) . . . . ? C6GA C1GA C2GA C3GA -1.9(8) . . . . ? N1GA C1GA C2GA C3GA 179.2(5) . . . . ? C6GA C1GA C2GA C7GA -179.1(5) . . . . ? N1GA C1GA C2GA C7GA 2.0(7) . . . . ? C1GA C6GA C5GA C4GA 0.2(9) . . . . ? C3GA C4GA C5GA C6GA -2.0(10) . . . . ? C5GA C4GA C3GA C2GA 1.9(10) . . . . ? C5GA C4GA C3GA C8GA 179.0(6) . . . . ? C1GA C2GA C3GA C4GA 0.1(8) . . . . ? C7GA C2GA C3GA C4GA 177.2(6) . . . . ? C1GA C2GA C3GA C8GA -177.0(6) . . . . ? C7GA C2GA C3GA C8GA 0.1(9) . . . . ? C6GB C1GB C2GB C3GB 0.0 . . . . ? N1GB C1GB C2GB C3GB 176.2(3) . . . . ? C6GB C1GB C2GB C7GB 179.9 . . . . ? N1GB C1GB C2GB C7GB -3.9(3) . . . . ? C1GB C2GB C3GB C4GB 0.0 . . . . ? C7GB C2GB C3GB C4GB -179.9 . . . . ? C1GB C2GB C3GB C8GB -178.8(5) . . . . ? C7GB C2GB C3GB C8GB 1.3(5) . . . . ? C2GB C3GB C4GB C5GB 0.0 . . . . ? C8GB C3GB C4GB C5GB 178.8(5) . . . . ? C3GB C4GB C5GB C6GB 0.0 . . . . ? C4GB C5GB C6GB C1GB 0.0 . . . . ? C2GB C1GB C6GB C5GB 0.0 . . . . ? N1GB C1GB C6GB C5GB -176.2(3) . . . . ? C6GC C1GC C2GC C3GC 0.0 . . . . ? N1GC C1GC C2GC C3GC 179.8(4) . . . . ? C6GC C1GC C2GC C7GC -178.5(4) . . . . ? N1GC C1GC C2GC C7GC 1.3(5) . . . . ? C1GC C2GC C3GC C4GC 0.0 . . . . ? C7GC C2GC C3GC C4GC 178.4(5) . . . . ? C1GC C2GC C3GC C8GC -178.5 . . . . ? C7GC C2GC C3GC C8GC 0.0(5) . . . . ? C2GC C3GC C4GC C5GC 0.0 . . . . ? C8GC C3GC C4GC C5GC 178.4 . . . . ? C3GC C4GC C5GC C6GC 0.0 . . . . ? C4GC C5GC C6GC C1GC 0.0 . . . . ? C2GC C1GC C6GC C5GC 0.0 . . . . ? N1GC C1GC C6GC C5GC -179.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1GA 0.972(16) 1.820(16) 2.767(5) 164(4) 7_655 O2 H2 N1GB 0.963(15) 1.798(16) 2.735(5) 163(4) 7_665 N1GA H1A1 O2 0.968(16) 2.123(17) 3.041(5) 158(4) . N1GB H1B1 O1 0.958(18) 2.089(16) 2.984(5) 155(4) . _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 24.66 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.968 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.064