# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Ayesha Jacobs' 'Luigi R Nassimbeni' 'Gaelle Ramon' 'Baganetsi K. Sebogisi' _publ_contact_author_name 'Ayesha Jacobs' _publ_contact_author_email JACOBSA@CPUT.AC.ZA _publ_section_title ; Inclusion Compounds of Hydroxynaphthoic acids ; # Attachment 'ALL.cif' data_c:\H1DIOX _database_code_depnum_ccdc_archive 'CCDC 770706' #TrackingRef 'ALL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-hydroxy-2-naphthoic acid 1,4-dioxane solvate ; _chemical_formula_moiety C11H8O3.0.5(C4H8O2) _chemical_formula_sum 'C13 H8 O4' _chemical_formula_weight 228.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4451(4) _cell_length_b 5.9568(3) _cell_length_c 24.7267(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.3190(10) _cell_angle_gamma 90.00 _cell_volume 1089.94(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.104 _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_reflns_number 9402 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2692 _reflns_number_gt 2229 _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^)+(0.1179P)^2^+0.3795P] 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 2692 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4514(2) 0.4064(2) 0.06760(5) 0.0412(4) Uani 1 1 d . . . C1 C 0.46189(19) 0.5827(3) 0.17063(6) 0.0246(3) Uani 1 1 d . . . H1 H 0.4093 0.4391 0.1633 0.030 Uiso 1 1 calc R . . H11 H 0.446(4) 0.376(6) 0.0337(13) 0.076(9) Uiso 1 1 d . . . O2 O 0.57038(19) 0.7174(2) 0.03591(5) 0.0405(4) Uani 1 1 d . . . C2 C 0.52872(19) 0.7013(3) 0.12943(6) 0.0260(3) Uani 1 1 d . . . O3 O 0.50691(19) 0.9499(2) 0.37910(5) 0.0385(3) Uani 1 1 d . . . C3 C 0.6058(2) 0.9171(3) 0.13997(6) 0.0284(4) Uani 1 1 d . . . H3 H 0.6509 0.9992 0.1114 0.034 Uiso 1 1 calc R . . C4 C 0.6155(2) 1.0070(3) 0.19093(6) 0.0270(3) Uani 1 1 d . . . H4 H 0.6674 1.1515 0.1974 0.032 Uiso 1 1 calc R . . C5 C 0.55946(19) 0.9781(3) 0.28767(6) 0.0254(3) Uani 1 1 d . . . H5 H 0.6115 1.1220 0.2951 0.031 Uiso 1 1 calc R . . C6 C 0.4942(2) 0.8576(3) 0.32867(6) 0.0275(3) Uani 1 1 d . . . C7 C 0.4152(2) 0.6430(3) 0.31812(6) 0.0287(4) Uani 1 1 d . . . H7 H 0.3695 0.5615 0.3467 0.034 Uiso 1 1 calc R . . C8 C 0.40469(19) 0.5531(3) 0.26688(6) 0.0253(3) Uani 1 1 d . . . H8 H 0.3523 0.4089 0.2602 0.030 Uiso 1 1 calc R . . C9 C 0.47080(18) 0.6724(3) 0.22375(6) 0.0227(3) Uani 1 1 d . . . C10 C 0.54923(18) 0.8885(2) 0.23447(6) 0.0228(3) Uani 1 1 d . . . C11 C 0.5201(2) 0.6088(3) 0.07376(6) 0.0294(4) Uani 1 1 d . . . H12 H 0.473(4) 0.864(5) 0.3987(11) 0.058(8) Uiso 1 1 d . . . O1G O 0.44893(19) 0.6679(2) 0.46194(6) 0.0458(4) Uani 1 1 d . . . C2G C 0.3598(5) 0.4568(5) 0.46183(13) 0.0956(14) Uani 1 1 d . . . C3G C 0.5436(5) 0.7203(6) 0.51657(15) 0.0358(7) Uani 0.50 1 d P . . C4G C 0.6301(5) 0.6624(7) 0.49185(15) 0.0424(9) Uani 0.50 1 d P . . 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 0.0613(9) 0.0341(7) 0.0280(6) -0.0044(5) 0.0036(6) -0.0097(6) C1 0.0221(7) 0.0229(7) 0.0281(7) -0.0013(5) -0.0006(5) 0.0003(5) O2 0.0545(8) 0.0406(7) 0.0264(6) -0.0007(5) 0.0042(5) -0.0103(6) C2 0.0241(7) 0.0278(8) 0.0253(7) 0.0004(6) -0.0012(5) 0.0017(5) O3 0.0559(8) 0.0328(7) 0.0276(6) -0.0062(5) 0.0079(5) -0.0071(6) C3 0.0284(7) 0.0275(8) 0.0288(7) 0.0048(6) 0.0009(6) -0.0026(6) C4 0.0263(7) 0.0219(7) 0.0321(7) 0.0019(6) -0.0004(5) -0.0030(5) C5 0.0233(7) 0.0213(7) 0.0309(7) -0.0019(6) -0.0005(5) 0.0004(5) C6 0.0276(7) 0.0270(8) 0.0274(7) -0.0039(6) 0.0013(5) 0.0025(6) C7 0.0283(7) 0.0284(8) 0.0298(7) 0.0015(6) 0.0050(6) -0.0022(6) C8 0.0233(7) 0.0220(7) 0.0307(7) -0.0003(5) 0.0028(5) -0.0017(5) C9 0.0181(6) 0.0212(7) 0.0284(7) -0.0001(5) 0.0003(5) 0.0007(5) C10 0.0184(6) 0.0213(7) 0.0282(7) 0.0003(5) -0.0003(5) 0.0019(5) C11 0.0291(8) 0.0314(8) 0.0266(7) 0.0000(6) -0.0017(6) 0.0012(6) O1G 0.0496(8) 0.0394(8) 0.0435(7) 0.0139(6) -0.0164(6) -0.0119(6) C2G 0.116(2) 0.0612(16) 0.091(2) 0.0418(15) -0.0736(19) -0.0542(17) C3G 0.0408(18) 0.0336(18) 0.0324(16) -0.0094(14) 0.0020(14) -0.0049(14) C4G 0.0378(18) 0.050(2) 0.0373(18) 0.0135(17) -0.0061(16) -0.0107(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.312(2) . ? C1 C2 1.377(2) . ? C1 C9 1.413(2) . ? O2 C11 1.229(2) . ? C2 C3 1.420(2) . ? C2 C11 1.478(2) . ? O3 C6 1.3569(19) . ? C3 C4 1.364(2) . ? C4 C10 1.421(2) . ? C5 C6 1.374(2) . ? C5 C10 1.414(2) . ? C6 C7 1.419(2) . ? C7 C8 1.370(2) . ? C8 C9 1.414(2) . ? C9 C10 1.426(2) . ? O1G C2G 1.421(3) . ? O1G C4G 1.466(4) . ? O1G C3G 1.487(4) . ? C2G C4G 1.343(4) 3_666 ? C2G C3G 1.353(5) 3_666 ? C3G C4G 0.997(5) . ? C3G C2G 1.353(5) 3_666 ? C4G C2G 1.343(4) 3_666 ? 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 120.64(14) . . ? C1 C2 C3 120.04(14) . . ? C1 C2 C11 121.03(14) . . ? C3 C2 C11 118.93(14) . . ? C4 C3 C2 120.28(14) . . ? C3 C4 C10 121.17(14) . . ? C6 C5 C10 120.12(14) . . ? O3 C6 C5 118.15(15) . . ? O3 C6 C7 121.31(15) . . ? C5 C6 C7 120.54(14) . . ? C8 C7 C6 120.17(14) . . ? C7 C8 C9 120.79(14) . . ? C1 C9 C8 121.77(14) . . ? C1 C9 C10 119.38(13) . . ? C8 C9 C10 118.85(13) . . ? C5 C10 C4 121.98(14) . . ? C5 C10 C9 119.53(13) . . ? C4 C10 C9 118.49(13) . . ? O2 C11 O1 122.85(15) . . ? O2 C11 C2 121.84(15) . . ? O1 C11 C2 115.29(14) . . ? C2G O1G C4G 112.6(2) . . ? C2G O1G C3G 111.2(2) . . ? C4G O1G C3G 39.5(2) . . ? C4G C2G C3G 43.4(2) 3_666 3_666 ? C4G C2G O1G 118.9(3) 3_666 . ? C3G C2G O1G 117.5(3) 3_666 . ? C4G C3G C2G 67.7(4) . 3_666 ? C4G C3G O1G 69.1(3) . . ? C2G C3G O1G 111.9(3) 3_666 . ? C3G C4G C2G 68.9(4) . 3_666 ? C3G C4G O1G 71.4(3) . . ? C2G C4G O1G 113.8(3) 3_666 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.628 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.068 #===END data_c:\H1DMSO _database_code_depnum_ccdc_archive 'CCDC 770707' #TrackingRef 'ALL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-hydroxy-2-naphthoic acid dimethyl sulphoxide solvate ; _chemical_formula_moiety 2C11H8O3.C2H6SO _chemical_formula_sum 'C24 H14 O7 S' _chemical_formula_weight 446.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 9.4013(10) _cell_length_b 10.0069(11) _cell_length_c 12.2414(13) _cell_angle_alpha 95.150(2) _cell_angle_beta 109.037(2) _cell_angle_gamma 90.332(2) _cell_volume 1083.5(2) _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 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.193 _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 12271 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.60 _reflns_number_total 4861 _reflns_number_gt 3530 _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^)+(0.1004P)^2^+1.1938P] 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 4861 _refine_ls_number_parameters 285 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.2046 _refine_ls_wR_factor_gt 0.1843 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4082(2) 0.3291(2) 0.82293(19) 0.0359(5) Uani 1 1 d . . . C1 C 0.1453(3) 0.1726(3) 0.7051(2) 0.0265(5) Uani 1 1 d . . . H1 H 0.1579 0.2567 0.6784 0.032 Uiso 1 1 calc R . . O2 O 0.4749(2) 0.1850(2) 0.95763(18) 0.0393(5) Uani 1 1 d . . . C2 C 0.2549(3) 0.1313(3) 0.7983(2) 0.0273(6) Uani 1 1 d . . . O3 O -0.3804(2) -0.1388(2) 0.48336(19) 0.0392(5) Uani 1 1 d D . . C3 C 0.2396(3) 0.0042(3) 0.8373(3) 0.0333(6) Uani 1 1 d . . . H3 H 0.3170 -0.0252 0.9013 0.040 Uiso 1 1 calc R . . C4 C 0.1135(3) -0.0758(3) 0.7827(3) 0.0331(6) Uani 1 1 d . . . H4 H 0.1044 -0.1611 0.8087 0.040 Uiso 1 1 calc R . . C5 C -0.1382(3) -0.1126(3) 0.6319(2) 0.0308(6) Uani 1 1 d . . . H2 H -0.1510 -0.1970 0.6581 0.037 Uiso 1 1 calc R . . C6 C -0.2486(3) -0.0680(3) 0.5406(2) 0.0305(6) Uani 1 1 d . . . C7 C -0.2303(3) 0.0556(3) 0.4993(2) 0.0318(6) Uani 1 1 d . . . H7 H -0.3073 0.0847 0.4349 0.038 Uiso 1 1 calc R . . C8 C -0.1027(3) 0.1336(3) 0.5514(2) 0.0299(6) Uani 1 1 d . . . H8 H -0.0915 0.2167 0.5226 0.036 Uiso 1 1 calc R . . H12A H -0.5017 -0.0949 0.3403 0.050(11) Uiso 1 1 d RD . . C9 C 0.0130(3) 0.0926(3) 0.6474(2) 0.0253(5) Uani 1 1 d . . . C10 C -0.0039(3) -0.0329(3) 0.6879(2) 0.0270(5) Uani 1 1 d . . . C11 C 0.3874(3) 0.2206(3) 0.8621(2) 0.0272(6) Uani 1 1 d . . . H12 H -0.383(4) -0.208(3) 0.518(3) 0.055(12) Uiso 1 1 d D . . O1A O -1.3584(2) -0.5134(2) -0.05873(17) 0.0327(5) Uani 1 1 d . . . C1A C -1.0930(3) -0.3626(3) 0.0512(2) 0.0255(5) Uani 1 1 d . . . H1A H -1.1608 -0.3358 -0.0190 0.031 Uiso 1 1 calc R . . O2A O -1.2996(2) -0.6541(2) 0.07976(18) 0.0352(5) Uani 1 1 d . . . C2A C -1.1290(3) -0.4733(3) 0.0964(2) 0.0256(5) Uani 1 1 d . . . O3A O -0.5588(2) -0.0649(2) 0.27449(17) 0.0327(5) Uani 1 1 d D . . C3A C -1.0278(3) -0.5140(3) 0.2008(2) 0.0293(6) Uani 1 1 d . . . H3A H -1.0530 -0.5904 0.2325 0.035 Uiso 1 1 calc R . . C4A C -0.8948(3) -0.4447(3) 0.2563(2) 0.0301(6) Uani 1 1 d . . . H4A H -0.8280 -0.4736 0.3260 0.036 Uiso 1 1 calc R . . C5A C -0.7183(3) -0.2543(3) 0.2678(2) 0.0260(5) Uani 1 1 d . . . H5A H -0.6488 -0.2822 0.3368 0.031 Uiso 1 1 calc R . . C6A C -0.6868(3) -0.1421(3) 0.2235(2) 0.0261(5) Uani 1 1 d . . . C7A C -0.7874(3) -0.1005(3) 0.1197(2) 0.0303(6) Uani 1 1 d . . . H7A H -0.7631 -0.0229 0.0891 0.036 Uiso 1 1 calc R . . C8A C -0.9190(3) -0.1712(3) 0.0635(2) 0.0301(6) Uani 1 1 d . . . H8A H -0.9861 -0.1420 -0.0059 0.036 Uiso 1 1 calc R . . C9A C -0.9570(3) -0.2876(3) 0.1069(2) 0.0241(5) Uani 1 1 d . . . C10A C -0.8549(3) -0.3295(3) 0.2111(2) 0.0240(5) Uani 1 1 d . . . C11A C -1.2706(3) -0.5518(3) 0.0361(2) 0.0264(5) Uani 1 1 d . . . S1G S -0.53614(10) -0.59329(9) 0.33543(8) 0.0374(2) Uiso 0.85 1 d P . . O2G O -0.5739(4) -0.6422(3) 0.4341(3) 0.0687(9) Uani 1 1 d . . . C3G C -0.5658(5) -0.7372(5) 0.2304(4) 0.0637(11) Uiso 1 1 d . . . C4G C -0.3371(5) -0.5771(5) 0.3758(4) 0.0704(12) Uiso 1 1 d . . . S5G S -0.4485(9) -0.6757(8) 0.3747(7) 0.0689(19) Uiso 0.15 1 d P . . 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 0.0227(9) 0.0330(11) 0.0457(12) -0.0022(9) 0.0042(8) -0.0033(8) C1 0.0235(12) 0.0238(13) 0.0322(13) -0.0032(11) 0.0108(10) -0.0019(10) O2 0.0288(10) 0.0479(13) 0.0344(11) -0.0006(10) 0.0027(8) -0.0091(9) C2 0.0184(11) 0.0315(14) 0.0303(13) -0.0052(11) 0.0080(10) -0.0028(10) O3 0.0263(10) 0.0459(13) 0.0352(11) 0.0027(10) -0.0030(8) -0.0152(9) C3 0.0239(13) 0.0377(16) 0.0338(15) 0.0031(12) 0.0035(11) -0.0009(11) C4 0.0292(13) 0.0310(15) 0.0364(15) 0.0072(12) 0.0063(11) -0.0048(11) C5 0.0268(13) 0.0335(15) 0.0303(14) -0.0005(12) 0.0079(11) -0.0061(11) C6 0.0224(12) 0.0374(15) 0.0279(13) -0.0074(11) 0.0061(10) -0.0089(11) C7 0.0245(13) 0.0353(15) 0.0302(14) -0.0017(12) 0.0030(11) -0.0022(11) C8 0.0279(13) 0.0271(14) 0.0314(14) 0.0010(11) 0.0056(11) -0.0016(10) C9 0.0217(12) 0.0252(13) 0.0289(13) -0.0022(11) 0.0095(10) 0.0008(10) C10 0.0239(12) 0.0321(14) 0.0259(13) 0.0009(11) 0.0099(10) 0.0008(10) C11 0.0203(12) 0.0291(14) 0.0312(13) -0.0063(11) 0.0095(10) -0.0017(10) O1A 0.0247(9) 0.0350(11) 0.0321(10) 0.0006(8) 0.0016(8) -0.0052(8) C1A 0.0187(11) 0.0303(14) 0.0245(12) -0.0031(10) 0.0042(9) 0.0011(10) O2A 0.0272(10) 0.0329(11) 0.0391(11) 0.0009(9) 0.0029(8) -0.0078(8) C2A 0.0169(11) 0.0281(13) 0.0283(13) -0.0077(11) 0.0052(10) -0.0017(9) O3A 0.0221(9) 0.0355(11) 0.0349(11) -0.0018(9) 0.0032(8) -0.0087(8) C3A 0.0232(12) 0.0283(14) 0.0327(14) 0.0015(11) 0.0047(10) -0.0030(10) C4A 0.0214(12) 0.0337(15) 0.0297(14) 0.0013(11) 0.0013(10) 0.0001(10) C5A 0.0173(11) 0.0310(14) 0.0254(12) -0.0030(10) 0.0026(9) 0.0000(10) C6A 0.0189(11) 0.0293(14) 0.0278(13) -0.0070(11) 0.0070(10) -0.0026(10) C7A 0.0277(13) 0.0306(14) 0.0320(14) 0.0020(11) 0.0094(11) -0.0031(11) C8A 0.0244(13) 0.0350(15) 0.0279(13) 0.0024(11) 0.0044(10) 0.0005(11) C9A 0.0188(11) 0.0273(13) 0.0242(12) -0.0038(10) 0.0057(9) 0.0019(9) C10A 0.0196(11) 0.0252(13) 0.0258(12) -0.0023(10) 0.0068(10) 0.0010(9) C11A 0.0191(11) 0.0288(14) 0.0288(13) -0.0062(11) 0.0067(10) -0.0011(10) O2G 0.106(2) 0.0521(16) 0.0601(17) -0.0032(13) 0.0469(17) -0.0333(16) _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 C11 1.265(3) . ? C1 C2 1.363(4) . ? C1 C9 1.415(4) . ? O2 C11 1.273(3) . ? C2 C3 1.420(4) . ? C2 C11 1.480(4) . ? O3 C6 1.365(3) . ? C3 C4 1.367(4) . ? C4 C10 1.417(4) . ? C5 C6 1.365(4) . ? C5 C10 1.423(4) . ? C6 C7 1.408(4) . ? C7 C8 1.362(4) . ? C8 C9 1.412(4) . ? C9 C10 1.416(4) . ? O1A C11A 1.279(3) . ? C1A C2A 1.370(4) . ? C1A C9A 1.412(3) . ? O2A C11A 1.264(3) . ? C2A C3A 1.418(4) . ? C2A C11A 1.475(3) . ? O3A C6A 1.358(3) . ? C3A C4A 1.363(4) . ? C4A C10A 1.421(4) . ? C5A C6A 1.362(4) . ? C5A C10A 1.418(3) . ? C6A C7A 1.413(4) . ? C7A C8A 1.361(4) . ? C8A C9A 1.413(4) . ? C9A C10A 1.423(3) . ? S1G S5G 1.187(8) . ? S1G O2G 1.486(3) . ? S1G C4G 1.775(5) . ? S1G C3G 1.798(5) . ? O2G S5G 1.597(9) . ? C3G S5G 1.800(10) . ? C4G S5G 1.431(9) . ? 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 121.2(2) . . ? C1 C2 C3 120.1(2) . . ? C1 C2 C11 120.2(2) . . ? C3 C2 C11 119.7(2) . . ? C4 C3 C2 120.0(3) . . ? C3 C4 C10 120.7(3) . . ? C6 C5 C10 120.1(3) . . ? C5 C6 O3 123.2(3) . . ? C5 C6 C7 120.7(2) . . ? O3 C6 C7 116.1(2) . . ? C8 C7 C6 120.2(3) . . ? C7 C8 C9 120.9(3) . . ? C8 C9 C1 122.3(2) . . ? C8 C9 C10 119.0(2) . . ? C1 C9 C10 118.8(2) . . ? C9 C10 C4 119.2(2) . . ? C9 C10 C5 119.1(2) . . ? C4 C10 C5 121.8(3) . . ? O1 C11 O2 122.6(2) . . ? O1 C11 C2 120.1(2) . . ? O2 C11 C2 117.3(2) . . ? C2A C1A C9A 121.2(2) . . ? C1A C2A C3A 119.6(2) . . ? C1A C2A C11A 120.5(2) . . ? C3A C2A C11A 119.9(2) . . ? C4A C3A C2A 120.8(3) . . ? C3A C4A C10A 120.7(2) . . ? C6A C5A C10A 120.0(2) . . ? O3A C6A C5A 122.8(2) . . ? O3A C6A C7A 116.4(2) . . ? C5A C6A C7A 120.8(2) . . ? C8A C7A C6A 120.3(3) . . ? C7A C8A C9A 120.8(3) . . ? C1A C9A C8A 122.3(2) . . ? C1A C9A C10A 119.1(2) . . ? C8A C9A C10A 118.7(2) . . ? C5A C10A C4A 122.0(2) . . ? C5A C10A C9A 119.4(2) . . ? C4A C10A C9A 118.7(2) . . ? O2A C11A O1A 122.9(2) . . ? O2A C11A C2A 118.8(2) . . ? O1A C11A C2A 118.3(2) . . ? S5G S1G O2G 72.4(4) . . ? S5G S1G C4G 53.4(4) . . ? O2G S1G C4G 108.0(2) . . ? S5G S1G C3G 70.8(4) . . ? O2G S1G C3G 105.00(19) . . ? C4G S1G C3G 98.3(2) . . ? S1G O2G S5G 45.1(3) . . ? S1G C3G S5G 38.5(3) . . ? S5G C4G S1G 41.8(3) . . ? S1G S5G C4G 84.9(5) . . ? S1G S5G O2G 62.5(4) . . ? C4G S5G O2G 121.6(6) . . ? S1G S5G C3G 70.7(4) . . ? C4G S5G C3G 113.1(6) . . ? O2G S5G C3G 100.4(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 C9 C1 C2 C3 1.7(4) . . . . ? C9 C1 C2 C11 -175.8(2) . . . . ? C1 C2 C3 C4 -1.2(4) . . . . ? C11 C2 C3 C4 176.3(3) . . . . ? C2 C3 C4 C10 -0.6(4) . . . . ? C10 C5 C6 O3 -179.7(3) . . . . ? C10 C5 C6 C7 1.2(4) . . . . ? C5 C6 C7 C8 -1.1(4) . . . . ? O3 C6 C7 C8 179.7(3) . . . . ? C6 C7 C8 C9 -0.2(4) . . . . ? C7 C8 C9 C1 -178.5(3) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? C2 C1 C9 C8 179.5(2) . . . . ? C2 C1 C9 C10 -0.4(4) . . . . ? C8 C9 C10 C4 178.7(3) . . . . ? C1 C9 C10 C4 -1.5(4) . . . . ? C8 C9 C10 C5 -1.2(4) . . . . ? C1 C9 C10 C5 178.6(2) . . . . ? C3 C4 C10 C9 2.0(4) . . . . ? C3 C4 C10 C5 -178.1(3) . . . . ? C6 C5 C10 C9 0.0(4) . . . . ? C6 C5 C10 C4 -179.9(3) . . . . ? C1 C2 C11 O1 -8.1(4) . . . . ? C3 C2 C11 O1 174.4(2) . . . . ? C1 C2 C11 O2 170.2(2) . . . . ? C3 C2 C11 O2 -7.3(4) . . . . ? C9A C1A C2A C3A -0.3(4) . . . . ? C9A C1A C2A C11A -179.1(2) . . . . ? C1A C2A C3A C4A -0.4(4) . . . . ? C11A C2A C3A C4A 178.4(2) . . . . ? C2A C3A C4A C10A 0.4(4) . . . . ? C10A C5A C6A O3A 179.2(2) . . . . ? C10A C5A C6A C7A -1.3(4) . . . . ? O3A C6A C7A C8A -179.4(2) . . . . ? C5A C6A C7A C8A 1.1(4) . . . . ? C6A C7A C8A C9A -0.5(4) . . . . ? C2A C1A C9A C8A -178.5(2) . . . . ? C2A C1A C9A C10A 1.0(4) . . . . ? C7A C8A C9A C1A 179.5(2) . . . . ? C7A C8A C9A C10A 0.1(4) . . . . ? C6A C5A C10A C4A -177.9(2) . . . . ? C6A C5A C10A C9A 0.9(4) . . . . ? C3A C4A C10A C5A 179.1(3) . . . . ? C3A C4A C10A C9A 0.3(4) . . . . ? C1A C9A C10A C5A -179.8(2) . . . . ? C8A C9A C10A C5A -0.3(4) . . . . ? C1A C9A C10A C4A -0.9(4) . . . . ? C8A C9A C10A C4A 178.5(2) . . . . ? C1A C2A C11A O2A 179.4(2) . . . . ? C3A C2A C11A O2A 0.6(4) . . . . ? C1A C2A C11A O1A -0.3(4) . . . . ? C3A C2A C11A O1A -179.1(2) . . . . ? C4G S1G O2G S5G -40.4(5) . . . . ? C3G S1G O2G S5G 63.8(5) . . . . ? O2G S1G C3G S5G -64.9(5) . . . . ? C4G S1G C3G S5G 46.4(4) . . . . ? O2G S1G C4G S5G 50.3(5) . . . . ? C3G S1G C4G S5G -58.5(5) . . . . ? O2G S1G S5G C4G -129.8(5) . . . . ? C3G S1G S5G C4G 116.7(5) . . . . ? C4G S1G S5G O2G 129.8(5) . . . . ? C3G S1G S5G O2G -113.5(3) . . . . ? O2G S1G S5G C3G 113.5(3) . . . . ? C4G S1G S5G C3G -116.7(5) . . . . ? S1G C4G S5G O2G -53.1(5) . . . . ? S1G C4G S5G C3G 66.4(5) . . . . ? S1G O2G S5G C4G 63.9(6) . . . . ? S1G O2G S5G C3G -61.6(4) . . . . ? S1G C3G S5G C4G -75.3(6) . . . . ? S1G C3G S5G O2G 55.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.786 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.074 #===END data_c:\H1DABCO _database_code_depnum_ccdc_archive 'CCDC 770708' #TrackingRef 'ALL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-hydroxy-2-naphthoic acid 1,4-diazabicyclo[2.2.2]octane salt ; _chemical_formula_moiety 2C11H8O3.2C6H12N2.3H20 _chemical_formula_sum 'C34 H46 N4 O9' _chemical_formula_weight 654.75 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1880(18) _cell_length_b 10.003(2) _cell_length_c 35.207(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.23(3) _cell_angle_gamma 90.00 _cell_volume 3234.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.29 _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.098 _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 27354 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.38 _reflns_number_total 8082 _reflns_number_gt 5997 _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^)+(0.0907P)^2^+1.4251P] 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 8082 _refine_ls_number_parameters 464 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1526 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.06681(14) 0.13944(14) 0.25761(3) 0.0252(3) Uani 1 1 d . . . C7 C 0.15833(17) 0.33394(18) 0.15631(5) 0.0194(3) Uani 1 1 d . . . C9 C 0.15468(17) 0.19192(18) 0.15824(5) 0.0194(3) Uani 1 1 d . . . O11 O 0.2953(2) 0.31515(16) 0.02658(4) 0.0432(4) Uani 1 1 d . . . C12 C 0.10105(17) 0.20259(18) 0.22510(5) 0.0201(3) Uani 1 1 d . . . C13 C 0.10791(18) 0.34416(18) 0.22348(5) 0.0216(3) Uani 1 1 d . . . H13 H 0.0940 0.3953 0.2459 0.026 Uiso 1 1 calc R . . N14 N 0.30267(18) 0.43010(16) -0.03828(4) 0.0254(3) Uani 1 1 d D . . C15 C 0.18668(18) 0.39611(18) 0.12125(5) 0.0216(3) Uani 1 1 d . . . H15 H 0.1872 0.4909 0.1197 0.026 Uiso 1 1 calc R . . C18 C 0.12392(18) 0.12874(18) 0.19310(5) 0.0211(3) Uani 1 1 d . . . H18 H 0.1191 0.0340 0.1943 0.025 Uiso 1 1 calc R . . N20 N 0.30469(17) 0.53000(16) -0.10419(4) 0.0242(3) Uani 1 1 d . . . C21 C 0.13437(19) 0.40732(18) 0.18999(5) 0.0222(3) Uani 1 1 d . . . H21 H 0.1368 0.5022 0.1892 0.027 Uiso 1 1 calc R . . C22 C 0.21351(18) 0.32240(19) 0.08931(5) 0.0227(4) Uani 1 1 d . . . C26 C 0.2134(2) 0.18112(19) 0.09177(5) 0.0260(4) Uani 1 1 d . . . H26 H 0.2342 0.1296 0.0699 0.031 Uiso 1 1 calc R . . C30 C 0.2416(2) 0.3884(2) 0.05192(5) 0.0267(4) Uani 1 1 d . . . C31 C 0.1842(2) 0.11794(19) 0.12497(5) 0.0248(4) Uani 1 1 d . . . H31 H 0.1836 0.0230 0.1259 0.030 Uiso 1 1 calc R . . O36 O 0.2129(2) 0.50726(16) 0.04724(4) 0.0548(5) Uani 1 1 d . . . C41 C 0.3269(3) 0.6343(2) -0.07569(6) 0.0391(5) Uani 1 1 d . . . H41A H 0.2461 0.6997 -0.0775 0.047 Uiso 1 1 calc R . . H41B H 0.4189 0.6823 -0.0806 0.047 Uiso 1 1 calc R . . C42 C 0.4241(2) 0.4300(2) -0.09988(6) 0.0336(4) Uani 1 1 d . . . H42A H 0.5192 0.4748 -0.1030 0.040 Uiso 1 1 calc R . . H42B H 0.4135 0.3610 -0.1199 0.040 Uiso 1 1 calc R . . C43 C 0.4197(3) 0.3639(3) -0.06078(6) 0.0434(6) Uani 1 1 d . . . H43A H 0.3987 0.2672 -0.0636 0.052 Uiso 1 1 calc R . . H43B H 0.5151 0.3739 -0.0475 0.052 Uiso 1 1 calc R . . C44 C 0.1662(2) 0.4613(3) -0.09782(6) 0.0406(5) Uani 1 1 d . . . H44A H 0.1542 0.3873 -0.1163 0.049 Uiso 1 1 calc R . . H44B H 0.0846 0.5247 -0.1019 0.049 Uiso 1 1 calc R . . C45 C 0.1619(3) 0.4053(3) -0.05722(7) 0.0457(6) Uani 1 1 d . . . H45A H 0.0834 0.4494 -0.0430 0.055 Uiso 1 1 calc R . . H45B H 0.1418 0.3081 -0.0580 0.055 Uiso 1 1 calc R . . C47 C 0.3335(3) 0.5746(2) -0.03570(6) 0.0458(6) Uani 1 1 d . . . H47A H 0.4312 0.5891 -0.0241 0.055 Uiso 1 1 calc R . . H47B H 0.2608 0.6187 -0.0196 0.055 Uiso 1 1 calc R . . N5 N 0.33321(15) 0.65402(15) -0.17289(4) 0.0200(3) Uani 1 1 d D . . N10 N 0.36323(16) 0.77494(16) -0.23501(4) 0.0247(3) Uani 1 1 d . . . C28 C 0.2527(2) 0.78314(18) -0.17161(5) 0.0238(4) Uani 1 1 d . . . H28A H 0.2891 0.8380 -0.1500 0.029 Uiso 1 1 calc R . . H28B H 0.1475 0.7665 -0.1683 0.029 Uiso 1 1 calc R . . C35 C 0.2729(2) 0.56895(19) -0.20419(5) 0.0271(4) Uani 1 1 d . . . H35A H 0.1693 0.5483 -0.1997 0.033 Uiso 1 1 calc R . . H35B H 0.3274 0.4837 -0.2055 0.033 Uiso 1 1 calc R . . C37 C 0.2772(2) 0.85682(19) -0.20937(5) 0.0261(4) Uani 1 1 d . . . H37A H 0.1820 0.8778 -0.2216 0.031 Uiso 1 1 calc R . . H37B H 0.3286 0.9422 -0.2043 0.031 Uiso 1 1 calc R . . C38 C 0.49110(19) 0.6791(2) -0.17885(5) 0.0281(4) Uani 1 1 d . . . H38A H 0.5453 0.5936 -0.1787 0.034 Uiso 1 1 calc R . . H38B H 0.5315 0.7364 -0.1582 0.034 Uiso 1 1 calc R . . C40 C 0.2877(2) 0.6469(2) -0.24150(5) 0.0326(4) Uani 1 1 d . . . H40A H 0.3429 0.5925 -0.2598 0.039 Uiso 1 1 calc R . . H40B H 0.1898 0.6640 -0.2527 0.039 Uiso 1 1 calc R . . C46 C 0.5059(2) 0.7492(3) -0.21739(6) 0.0373(5) Uani 1 1 d . . . H46A H 0.5583 0.8349 -0.2137 0.045 Uiso 1 1 calc R . . H46B H 0.5638 0.6924 -0.2344 0.045 Uiso 1 1 calc R . . O2 O 0.40451(17) 0.84460(16) -0.31155(4) 0.0308(3) Uani 1 1 d . . . O5 O 0.67322(15) 0.72736(15) -0.30394(4) 0.0330(3) Uani 1 1 d . . . O6 O 0.90579(14) 0.71180(15) -0.31817(4) 0.0303(3) Uani 1 1 d . . . O3 O 0.17561(19) 0.72383(18) -0.35270(4) 0.0397(4) Uani 1 1 d . . . O4 O 0.65242(18) 0.33997(16) -0.52293(4) 0.0360(3) Uani 1 1 d . . . C6 C 0.7722(2) 0.68976(18) -0.32490(5) 0.0225(3) Uani 1 1 d . . . C17 C 0.64041(19) 0.48552(17) -0.42850(5) 0.0219(3) Uani 1 1 d . . . C8 C 0.6991(2) 0.39291(18) -0.48946(5) 0.0256(4) Uani 1 1 d . . . C19 C 0.58147(19) 0.58582(18) -0.36810(5) 0.0232(4) Uani 1 1 d . . . H19 H 0.5110 0.6100 -0.3500 0.028 Uiso 1 1 calc R . . C10 C 0.8915(2) 0.4714(2) -0.44789(5) 0.0294(4) Uani 1 1 d . . . H10 H 0.9923 0.4855 -0.4428 0.035 Uiso 1 1 calc R . . C11 C 0.83145(19) 0.57559(18) -0.38622(5) 0.0231(4) Uani 1 1 d . . . H11 H 0.9316 0.5928 -0.3810 0.028 Uiso 1 1 calc R . . C20 C 0.78906(19) 0.51034(18) -0.42059(5) 0.0222(4) Uani 1 1 d . . . C23 C 0.53779(19) 0.52443(19) -0.40104(5) 0.0248(4) Uani 1 1 d . . . H23 H 0.4372 0.5075 -0.4057 0.030 Uiso 1 1 calc R . . C14 C 0.5972(2) 0.42611(19) -0.46336(5) 0.0256(4) Uani 1 1 d . . . H14 H 0.4971 0.4092 -0.4687 0.031 Uiso 1 1 calc R . . C24 C 0.8480(2) 0.4139(2) -0.48141(5) 0.0289(4) Uani 1 1 d . . . H24 H 0.9184 0.3879 -0.4993 0.035 Uiso 1 1 calc R . . C16 C 0.72989(19) 0.61391(17) -0.36054(5) 0.0207(3) Uani 1 1 d . . . H16 H 0.726(3) 0.321(3) -0.5373(8) 0.049(8) Uiso 1 1 d . . . H1 H 0.075(3) 0.191(3) 0.2761(8) 0.048(8) Uiso 1 1 d . . . O7 O 0.85103(18) 0.25423(18) -0.57016(4) 0.0380(4) Uani 1 1 d . . . H4 H 0.478(3) 0.810(3) -0.3139(7) 0.041(7) Uiso 1 1 d . . . H12 H 0.383(3) 0.837(3) -0.2867(8) 0.042(7) Uiso 1 1 d . . . H7 H 0.244(4) 0.759(3) -0.3406(9) 0.061(9) Uiso 1 1 d . . . H2 H 0.091(4) 0.731(3) -0.3409(9) 0.064(9) Uiso 1 1 d . . . H3 H 0.838(3) 0.263(3) -0.5955(10) 0.066(9) Uiso 1 1 d . . . H5 H 0.844(3) 0.172(3) -0.5672(8) 0.051(8) Uiso 1 1 d . . . H6 H 0.324(3) 0.610(2) -0.1497(4) 0.039(6) Uiso 1 1 d D . . H8 H 0.296(3) 0.389(3) -0.0145(4) 0.057(8) 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 0.0347(7) 0.0256(7) 0.0153(6) 0.0023(5) -0.0003(5) -0.0048(5) C7 0.0150(7) 0.0221(9) 0.0211(7) 0.0014(6) 0.0004(6) -0.0006(6) C9 0.0163(7) 0.0218(8) 0.0202(7) 0.0002(6) 0.0009(6) 0.0000(6) O11 0.0696(11) 0.0361(8) 0.0248(7) 0.0084(6) 0.0183(7) 0.0131(8) C12 0.0164(7) 0.0255(9) 0.0182(7) 0.0032(6) -0.0023(6) -0.0032(6) C13 0.0210(8) 0.0237(9) 0.0199(7) -0.0019(7) 0.0001(6) -0.0013(7) N14 0.0360(8) 0.0230(8) 0.0173(7) 0.0021(6) 0.0019(6) -0.0021(6) C15 0.0198(8) 0.0212(8) 0.0238(8) 0.0033(7) 0.0014(6) -0.0006(6) C18 0.0225(8) 0.0196(8) 0.0213(8) 0.0020(6) 0.0001(6) -0.0008(6) N20 0.0295(8) 0.0237(8) 0.0192(7) 0.0011(6) -0.0030(6) 0.0011(6) C21 0.0232(8) 0.0197(8) 0.0239(8) -0.0007(7) 0.0013(6) -0.0018(7) C22 0.0197(8) 0.0272(9) 0.0213(8) 0.0039(7) 0.0025(6) -0.0002(7) C26 0.0300(9) 0.0255(9) 0.0228(8) -0.0025(7) 0.0049(7) 0.0026(7) C30 0.0298(9) 0.0295(10) 0.0208(8) 0.0041(7) 0.0027(7) -0.0019(8) C31 0.0291(9) 0.0204(9) 0.0249(8) -0.0001(7) 0.0034(7) 0.0016(7) O36 0.1088(16) 0.0277(8) 0.0289(7) 0.0066(6) 0.0234(9) 0.0097(9) C41 0.0635(15) 0.0268(11) 0.0270(10) -0.0017(8) -0.0009(9) -0.0005(10) C42 0.0362(11) 0.0361(11) 0.0285(9) 0.0018(8) 0.0022(8) 0.0043(9) C43 0.0494(13) 0.0474(14) 0.0337(11) 0.0104(10) 0.0081(9) 0.0209(11) C44 0.0335(11) 0.0489(14) 0.0392(11) 0.0011(10) -0.0076(9) -0.0001(10) C45 0.0371(12) 0.0581(16) 0.0418(12) 0.0035(11) 0.0016(9) -0.0110(11) C47 0.0808(18) 0.0318(12) 0.0247(10) -0.0011(8) 0.0009(10) -0.0115(12) N5 0.0205(7) 0.0210(7) 0.0184(6) 0.0004(6) -0.0021(5) 0.0012(6) N10 0.0231(7) 0.0313(8) 0.0198(7) 0.0011(6) 0.0018(6) 0.0008(6) C28 0.0265(9) 0.0223(9) 0.0230(8) -0.0003(7) 0.0045(7) 0.0047(7) C35 0.0310(9) 0.0235(9) 0.0266(9) -0.0035(7) -0.0054(7) -0.0023(7) C37 0.0300(9) 0.0233(9) 0.0250(8) 0.0033(7) 0.0022(7) 0.0039(7) C38 0.0176(8) 0.0373(11) 0.0290(9) 0.0014(8) -0.0044(7) 0.0017(7) C40 0.0457(12) 0.0306(10) 0.0213(8) -0.0055(8) -0.0041(8) -0.0005(9) C46 0.0200(9) 0.0582(14) 0.0339(10) 0.0113(10) 0.0037(8) 0.0036(9) O2 0.0305(8) 0.0378(8) 0.0243(7) 0.0021(6) 0.0039(6) 0.0027(6) O5 0.0265(7) 0.0457(9) 0.0271(7) -0.0121(6) 0.0032(5) 0.0017(6) O6 0.0253(7) 0.0442(8) 0.0216(6) -0.0072(6) 0.0012(5) -0.0051(6) O3 0.0356(8) 0.0538(10) 0.0299(7) -0.0115(7) 0.0069(7) -0.0101(8) O4 0.0411(8) 0.0426(9) 0.0240(7) -0.0125(6) -0.0059(6) 0.0043(7) C6 0.0274(9) 0.0214(8) 0.0186(7) 0.0010(6) -0.0002(6) -0.0004(7) C17 0.0273(9) 0.0178(8) 0.0207(8) 0.0017(6) -0.0018(6) 0.0003(7) C8 0.0354(10) 0.0217(9) 0.0196(8) -0.0012(7) -0.0038(7) 0.0011(7) C19 0.0240(8) 0.0239(9) 0.0218(8) 0.0005(7) 0.0029(6) -0.0007(7) C10 0.0265(9) 0.0379(11) 0.0236(8) -0.0026(8) 0.0017(7) -0.0015(8) C11 0.0227(8) 0.0264(9) 0.0202(8) -0.0006(7) 0.0003(6) -0.0024(7) C20 0.0257(9) 0.0227(9) 0.0181(7) 0.0008(6) 0.0012(6) -0.0011(7) C23 0.0223(8) 0.0266(9) 0.0254(8) -0.0012(7) -0.0007(7) -0.0020(7) C14 0.0279(9) 0.0251(9) 0.0236(8) -0.0013(7) -0.0053(7) 0.0005(7) C24 0.0316(10) 0.0343(11) 0.0211(8) -0.0027(7) 0.0053(7) 0.0014(8) C16 0.0254(8) 0.0189(8) 0.0179(7) 0.0012(6) -0.0003(6) -0.0015(6) O7 0.0507(10) 0.0366(9) 0.0268(7) -0.0033(7) 0.0050(6) -0.0080(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.350(2) . ? O1 H1 0.83(3) . ? C7 C15 1.411(2) . ? C7 C21 1.416(2) . ? C7 C9 1.423(2) . ? C9 C18 1.415(2) . ? C9 C31 1.417(2) . ? O11 C30 1.263(2) . ? C12 C18 1.367(2) . ? C12 C13 1.419(3) . ? C13 C21 1.364(2) . ? C13 H13 0.9500 . ? N14 C45 1.464(3) . ? N14 C47 1.475(3) . ? N14 C43 1.504(3) . ? N14 H8 0.935(10) . ? C15 C22 1.371(2) . ? C15 H15 0.9500 . ? C18 H18 0.9500 . ? N20 C41 1.459(3) . ? N20 C44 1.468(3) . ? N20 C42 1.490(3) . ? C21 H21 0.9500 . ? C22 C26 1.416(3) . ? C22 C30 1.500(2) . ? C26 C31 1.361(3) . ? C26 H26 0.9500 . ? C30 O36 1.228(3) . ? C31 H31 0.9500 . ? C41 C47 1.530(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.529(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.537(3) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? N5 C35 1.490(2) . ? N5 C28 1.490(2) . ? N5 C38 1.492(2) . ? N5 H6 0.930(10) . ? N10 C46 1.461(2) . ? N10 C37 1.463(2) . ? N10 C40 1.472(3) . ? C28 C37 1.541(2) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C35 C40 1.536(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C46 1.536(3) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? O2 H4 0.77(3) . ? O2 H12 0.90(3) . ? O5 C6 1.242(2) . ? O6 C6 1.265(2) . ? O3 H7 0.83(3) . ? O3 H2 0.89(3) . ? O4 C8 1.353(2) . ? O4 H16 0.88(3) . ? C6 C16 1.510(2) . ? C17 C20 1.410(2) . ? C17 C14 1.413(2) . ? C17 C23 1.419(2) . ? C8 C14 1.366(3) . ? C8 C24 1.407(3) . ? C19 C23 1.365(2) . ? C19 C16 1.412(2) . ? C19 H19 0.9500 . ? C10 C24 1.365(3) . ? C10 C20 1.415(2) . ? C10 H10 0.9500 . ? C11 C16 1.368(2) . ? C11 C20 1.422(2) . ? C11 H11 0.9500 . ? C23 H23 0.9500 . ? C14 H14 0.9500 . ? C24 H24 0.9500 . ? O7 H3 0.90(3) . ? O7 H5 0.83(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 H1 110.5(19) . . ? C15 C7 C21 122.62(16) . . ? C15 C7 C9 119.12(15) . . ? C21 C7 C9 118.26(15) . . ? C18 C9 C31 121.96(16) . . ? C18 C9 C7 119.53(15) . . ? C31 C9 C7 118.50(15) . . ? O1 C12 C18 119.23(16) . . ? O1 C12 C13 120.81(15) . . ? C18 C12 C13 119.91(15) . . ? C21 C13 C12 120.38(16) . . ? C21 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C45 N14 C47 111.14(19) . . ? C45 N14 C43 108.68(17) . . ? C47 N14 C43 109.01(18) . . ? C45 N14 H8 104.9(17) . . ? C47 N14 H8 113.1(18) . . ? C43 N14 H8 110.0(18) . . ? C22 C15 C7 121.34(17) . . ? C22 C15 H15 119.3 . . ? C7 C15 H15 119.3 . . ? C12 C18 C9 120.71(16) . . ? C12 C18 H18 119.6 . . ? C9 C18 H18 119.6 . . ? C41 N20 C44 109.80(17) . . ? C41 N20 C42 108.55(16) . . ? C44 N20 C42 108.01(16) . . ? C13 C21 C7 121.18(16) . . ? C13 C21 H21 119.4 . . ? C7 C21 H21 119.4 . . ? C15 C22 C26 119.09(16) . . ? C15 C22 C30 121.37(17) . . ? C26 C22 C30 119.54(16) . . ? C31 C26 C22 121.10(17) . . ? C31 C26 H26 119.4 . . ? C22 C26 H26 119.4 . . ? O36 C30 O11 123.54(17) . . ? O36 C30 C22 120.20(17) . . ? O11 C30 C22 116.25(17) . . ? C26 C31 C9 120.82(17) . . ? C26 C31 H31 119.6 . . ? C9 C31 H31 119.6 . . ? N20 C41 C47 110.85(17) . . ? N20 C41 H41A 109.5 . . ? C47 C41 H41A 109.5 . . ? N20 C41 H41B 109.5 . . ? C47 C41 H41B 109.5 . . ? H41A C41 H41B 108.1 . . ? N20 C42 C43 110.42(16) . . ? N20 C42 H42A 109.6 . . ? C43 C42 H42A 109.6 . . ? N20 C42 H42B 109.6 . . ? C43 C42 H42B 109.6 . . ? H42A C42 H42B 108.1 . . ? N14 C43 C42 108.45(17) . . ? N14 C43 H43A 110.0 . . ? C42 C43 H43A 110.0 . . ? N14 C43 H43B 110.0 . . ? C42 C43 H43B 110.0 . . ? H43A C43 H43B 108.4 . . ? N20 C44 C45 110.65(17) . . ? N20 C44 H44A 109.5 . . ? C45 C44 H44A 109.5 . . ? N20 C44 H44B 109.5 . . ? C45 C44 H44B 109.5 . . ? H44A C44 H44B 108.1 . . ? N14 C45 C44 108.78(17) . . ? N14 C45 H45A 109.9 . . ? C44 C45 H45A 109.9 . . ? N14 C45 H45B 109.9 . . ? C44 C45 H45B 109.9 . . ? H45A C45 H45B 108.3 . . ? N14 C47 C41 108.81(16) . . ? N14 C47 H47A 109.9 . . ? C41 C47 H47A 109.9 . . ? N14 C47 H47B 109.9 . . ? C41 C47 H47B 109.9 . . ? H47A C47 H47B 108.3 . . ? C35 N5 C28 109.91(14) . . ? C35 N5 C38 109.83(14) . . ? C28 N5 C38 110.09(14) . . ? C35 N5 H6 109.9(15) . . ? C28 N5 H6 108.9(15) . . ? C38 N5 H6 108.1(15) . . ? C46 N10 C37 109.17(15) . . ? C46 N10 C40 109.17(17) . . ? C37 N10 C40 108.90(15) . . ? N5 C28 C37 107.86(14) . . ? N5 C28 H28A 110.1 . . ? C37 C28 H28A 110.1 . . ? N5 C28 H28B 110.1 . . ? C37 C28 H28B 110.1 . . ? H28A C28 H28B 108.4 . . ? N5 C35 C40 107.73(15) . . ? N5 C35 H35A 110.2 . . ? C40 C35 H35A 110.2 . . ? N5 C35 H35B 110.2 . . ? C40 C35 H35B 110.2 . . ? H35A C35 H35B 108.5 . . ? N10 C37 C28 110.82(15) . . ? N10 C37 H37A 109.5 . . ? C28 C37 H37A 109.5 . . ? N10 C37 H37B 109.5 . . ? C28 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? N5 C38 C46 107.82(14) . . ? N5 C38 H38A 110.1 . . ? C46 C38 H38A 110.1 . . ? N5 C38 H38B 110.1 . . ? C46 C38 H38B 110.1 . . ? H38A C38 H38B 108.5 . . ? N10 C40 C35 111.03(15) . . ? N10 C40 H40A 109.4 . . ? C35 C40 H40A 109.4 . . ? N10 C40 H40B 109.4 . . ? C35 C40 H40B 109.4 . . ? H40A C40 H40B 108.0 . . ? N10 C46 C38 111.08(15) . . ? N10 C46 H46A 109.4 . . ? C38 C46 H46A 109.4 . . ? N10 C46 H46B 109.4 . . ? C38 C46 H46B 109.4 . . ? H46A C46 H46B 108.0 . . ? H4 O2 H12 106(2) . . ? H7 O3 H2 113(3) . . ? C8 O4 H16 110.6(18) . . ? O5 C6 O6 123.79(16) . . ? O5 C6 C16 117.87(16) . . ? O6 C6 C16 118.34(15) . . ? C20 C17 C14 119.91(16) . . ? C20 C17 C23 118.16(16) . . ? C14 C17 C23 121.92(17) . . ? O4 C8 C14 118.17(17) . . ? O4 C8 C24 121.47(17) . . ? C14 C8 C24 120.36(16) . . ? C23 C19 C16 120.99(16) . . ? C23 C19 H19 119.5 . . ? C16 C19 H19 119.5 . . ? C24 C10 C20 121.10(18) . . ? C24 C10 H10 119.4 . . ? C20 C10 H10 119.4 . . ? C16 C11 C20 120.85(16) . . ? C16 C11 H11 119.6 . . ? C20 C11 H11 119.6 . . ? C17 C20 C10 118.25(16) . . ? C17 C20 C11 119.70(16) . . ? C10 C20 C11 122.04(16) . . ? C19 C23 C17 120.97(17) . . ? C19 C23 H23 119.5 . . ? C17 C23 H23 119.5 . . ? C8 C14 C17 120.18(17) . . ? C8 C14 H14 119.9 . . ? C17 C14 H14 119.9 . . ? C10 C24 C8 120.16(17) . . ? C10 C24 H24 119.9 . . ? C8 C24 H24 119.9 . . ? C11 C16 C19 119.30(16) . . ? C11 C16 C6 121.54(16) . . ? C19 C16 C6 119.14(15) . . ? H3 O7 H5 102(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C7 C9 C18 -178.94(15) . . . . ? C21 C7 C9 C18 1.6(2) . . . . ? C15 C7 C9 C31 1.9(2) . . . . ? C21 C7 C9 C31 -177.57(15) . . . . ? O1 C12 C13 C21 -176.23(15) . . . . ? C18 C12 C13 C21 1.3(3) . . . . ? C21 C7 C15 C22 178.15(16) . . . . ? C9 C7 C15 C22 -1.3(2) . . . . ? O1 C12 C18 C9 177.66(15) . . . . ? C13 C12 C18 C9 0.1(2) . . . . ? C31 C9 C18 C12 177.59(16) . . . . ? C7 C9 C18 C12 -1.5(2) . . . . ? C12 C13 C21 C7 -1.2(3) . . . . ? C15 C7 C21 C13 -179.68(16) . . . . ? C9 C7 C21 C13 -0.2(2) . . . . ? C7 C15 C22 C26 -0.4(3) . . . . ? C7 C15 C22 C30 179.15(16) . . . . ? C15 C22 C26 C31 1.4(3) . . . . ? C30 C22 C26 C31 -178.09(17) . . . . ? C15 C22 C30 O36 -14.6(3) . . . . ? C26 C22 C30 O36 164.9(2) . . . . ? C15 C22 C30 O11 165.30(18) . . . . ? C26 C22 C30 O11 -15.2(3) . . . . ? C22 C26 C31 C9 -0.8(3) . . . . ? C18 C9 C31 C26 179.98(17) . . . . ? C7 C9 C31 C26 -0.9(3) . . . . ? C44 N20 C41 C47 61.0(2) . . . . ? C42 N20 C41 C47 -56.9(2) . . . . ? C41 N20 C42 C43 62.2(2) . . . . ? C44 N20 C42 C43 -56.8(2) . . . . ? C45 N14 C43 C42 63.7(2) . . . . ? C47 N14 C43 C42 -57.6(2) . . . . ? N20 C42 C43 N14 -4.5(3) . . . . ? C41 N20 C44 C45 -56.0(2) . . . . ? C42 N20 C44 C45 62.2(2) . . . . ? C47 N14 C45 C44 61.3(2) . . . . ? C43 N14 C45 C44 -58.7(2) . . . . ? N20 C44 C45 N14 -4.0(3) . . . . ? C45 N14 C47 C41 -56.6(3) . . . . ? C43 N14 C47 C41 63.2(2) . . . . ? N20 C41 C47 N14 -4.7(3) . . . . ? C35 N5 C28 C37 -62.68(18) . . . . ? C38 N5 C28 C37 58.42(18) . . . . ? C28 N5 C35 C40 58.72(19) . . . . ? C38 N5 C35 C40 -62.54(19) . . . . ? C46 N10 C37 C28 -61.6(2) . . . . ? C40 N10 C37 C28 57.55(19) . . . . ? N5 C28 C37 N10 3.2(2) . . . . ? C35 N5 C38 C46 59.2(2) . . . . ? C28 N5 C38 C46 -61.93(19) . . . . ? C46 N10 C40 C35 57.4(2) . . . . ? C37 N10 C40 C35 -61.7(2) . . . . ? N5 C35 C40 N10 3.4(2) . . . . ? C37 N10 C46 C38 58.0(2) . . . . ? C40 N10 C46 C38 -60.9(2) . . . . ? N5 C38 C46 N10 2.8(2) . . . . ? C14 C17 C20 C10 -1.5(3) . . . . ? C23 C17 C20 C10 179.88(17) . . . . ? C14 C17 C20 C11 177.18(16) . . . . ? C23 C17 C20 C11 -1.5(3) . . . . ? C24 C10 C20 C17 1.4(3) . . . . ? C24 C10 C20 C11 -177.25(19) . . . . ? C16 C11 C20 C17 0.5(3) . . . . ? C16 C11 C20 C10 179.05(18) . . . . ? C16 C19 C23 C17 0.8(3) . . . . ? C20 C17 C23 C19 0.9(3) . . . . ? C14 C17 C23 C19 -177.75(18) . . . . ? O4 C8 C14 C17 -178.02(17) . . . . ? C24 C8 C14 C17 1.9(3) . . . . ? C20 C17 C14 C8 -0.1(3) . . . . ? C23 C17 C14 C8 178.45(18) . . . . ? C20 C10 C24 C8 0.4(3) . . . . ? O4 C8 C24 C10 177.90(19) . . . . ? C14 C8 C24 C10 -2.0(3) . . . . ? C20 C11 C16 C19 1.2(3) . . . . ? C20 C11 C16 C6 -176.72(16) . . . . ? C23 C19 C16 C11 -1.8(3) . . . . ? C23 C19 C16 C6 176.15(16) . . . . ? O5 C6 C16 C11 176.24(17) . . . . ? O6 C6 C16 C11 -3.5(3) . . . . ? O5 C6 C16 C19 -1.7(2) . . . . ? O6 C6 C16 C19 178.63(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.930 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.058 #===END data_c:\H2DABCO _database_code_depnum_ccdc_archive 'CCDC 770709' #TrackingRef 'ALL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-hydroxy-2-naphthoic acid 1,4-diazabicyclo[2.2.2]octane salt ; _chemical_formula_moiety 2C11H8O3.C6H12N2 _chemical_formula_sum 'C28 H28 N2 O6' _chemical_formula_weight 488.52 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.768(2) _cell_length_b 24.064(5) _cell_length_c 9.5656(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.12(3) _cell_angle_gamma 90.00 _cell_volume 2440.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 'All data' _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.094 _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 'Bruker Apex duo' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 25972 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.46 _reflns_number_total 6001 _reflns_number_gt 4870 _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^)+(0.0560P)^2^+0.8323P] 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 6001 _refine_ls_number_parameters 345 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.18816(10) 0.46063(5) 0.62570(11) 0.0417(3) Uani 1 1 d . . . C1 C 0.18674(11) 0.38879(5) 0.85250(12) 0.0248(2) Uani 1 1 d . . . H1 H 0.3347(17) 0.4652(7) 0.4470(12) 0.056(5) Uiso 1 1 d D . . O2 O 0.38152(9) 0.43432(5) 0.60130(11) 0.0395(2) Uani 1 1 d . . . C2 C 0.29064(12) 0.39301(5) 0.78532(13) 0.0265(2) Uani 1 1 d . . . O3 O 0.08249(9) 0.41984(4) 0.81232(10) 0.0341(2) Uani 1 1 d . . . C3 C 0.39843(12) 0.36025(6) 0.83348(15) 0.0336(3) Uani 1 1 d . . . H3 H 0.4690 0.3628 0.7865 0.040 Uiso 1 1 calc R . . C4 C 0.40356(13) 0.32509(6) 0.94563(16) 0.0381(3) Uani 1 1 d . . . H4 H 0.4779 0.3041 0.9774 0.046 Uiso 1 1 calc R . . C5 C 0.29879(16) 0.28274(7) 1.13153(18) 0.0464(4) Uani 1 1 d . . . H5 H 0.3721 0.2614 1.1654 0.056 Uiso 1 1 calc R . . C6 C 0.19559(17) 0.27757(7) 1.19509(18) 0.0504(4) Uani 1 1 d . . . H6 H 0.1978 0.2526 1.2725 0.060 Uiso 1 1 calc R . . C7 C 0.08615(16) 0.30865(6) 1.14747(17) 0.0419(3) Uani 1 1 d . . . H7 H 0.0146 0.3045 1.1923 0.050 Uiso 1 1 calc R . . C8 C 0.08212(13) 0.34498(5) 1.03641(14) 0.0322(3) Uani 1 1 d . . . H8 H 0.0079 0.3661 1.0048 0.039 Uiso 1 1 calc R . . C9 C 0.18775(12) 0.35116(5) 0.96871(12) 0.0261(2) Uani 1 1 d . . . C10 C 0.29834(13) 0.31957(5) 1.01552(14) 0.0322(3) Uani 1 1 d . . . H10 H 0.215(4) 0.5391(15) 0.035(2) 0.047(10) Uiso 0.50 1 d PD . . H11 H 0.103(2) 0.4412(9) 0.736(2) 0.072(6) Uiso 1 1 d . . . C12 C 0.28671(13) 0.43197(5) 0.66319(13) 0.0306(3) Uani 1 1 d . . . C18 C 0.25087(13) 0.59170(5) -0.17640(13) 0.0317(3) Uani 1 1 d . . . O1A O 0.36337(10) 0.59017(5) -0.11588(11) 0.0446(3) Uani 1 1 d . . . C1A C 0.30797(12) 0.64642(5) -0.37551(13) 0.0256(2) Uani 1 1 d . . . O2A O 0.16017(10) 0.56926(4) -0.12473(10) 0.0395(2) Uani 1 1 d D . . C2A C 0.21629(12) 0.62057(5) -0.31481(13) 0.0280(3) Uani 1 1 d . . . O3A O 0.42932(9) 0.64833(4) -0.31146(11) 0.0355(2) Uani 1 1 d . . . C3A C 0.08847(13) 0.62152(6) -0.38617(14) 0.0345(3) Uani 1 1 d . . . H3A H 0.0254 0.6039 -0.3438 0.041 Uiso 1 1 calc R . . C4A C 0.05522(13) 0.64714(6) -0.51325(14) 0.0349(3) Uani 1 1 d . . . H4A H -0.0308 0.6479 -0.5581 0.042 Uiso 1 1 calc R . . C5A C 0.11716(14) 0.69853(5) -0.71514(14) 0.0324(3) Uani 1 1 d . . . H5A H 0.0318 0.6994 -0.7623 0.039 Uiso 1 1 calc R . . C6A C 0.20862(15) 0.72190(6) -0.77818(16) 0.0385(3) Uani 1 1 d . . . H6A H 0.1864 0.7388 -0.8688 0.046 Uiso 1 1 calc R . . C7A C 0.33499(15) 0.72117(6) -0.71065(17) 0.0410(3) Uani 1 1 d . . . H7A H 0.3977 0.7376 -0.7559 0.049 Uiso 1 1 calc R . . C8A C 0.36884(13) 0.69703(5) -0.58005(15) 0.0339(3) Uani 1 1 d . . . H8A H 0.4548 0.6968 -0.5350 0.041 Uiso 1 1 calc R . . C9A C 0.27615(12) 0.67252(4) -0.51195(13) 0.0258(2) Uani 1 1 d . . . C10A C 0.14809(12) 0.67291(5) -0.57979(13) 0.0274(3) Uani 1 1 d . . . H10A H 0.199(3) 0.5500(14) -0.034(2) 0.043(9) Uiso 0.50 1 d PD . . H11A H 0.430(2) 0.6287(10) -0.227(2) 0.076(7) Uiso 1 1 d . . . N1G N 0.24067(11) 0.52398(4) 0.11526(11) 0.0279(2) Uani 1 1 d D . . N2G N 0.30846(10) 0.48158(4) 0.35571(11) 0.0266(2) Uani 1 1 d D . . C3G C 0.25768(15) 0.56841(5) 0.22368(14) 0.0351(3) Uani 1 1 d . . . H31A H 0.1766 0.5879 0.2230 0.042 Uiso 1 1 calc R . . H31B H 0.3200 0.5958 0.2016 0.042 Uiso 1 1 calc R . . C4G C 0.30388(13) 0.54308(5) 0.37072(14) 0.0305(3) Uani 1 1 d . . . H25A H 0.3888 0.5575 0.4105 0.037 Uiso 1 1 calc R . . H25B H 0.2457 0.5532 0.4361 0.037 Uiso 1 1 calc R . . C5G C 0.14144(12) 0.48557(5) 0.14547(14) 0.0300(3) Uani 1 1 d . . . H21A H 0.1287 0.4555 0.0737 0.036 Uiso 1 1 calc R . . H21B H 0.0608 0.5059 0.1402 0.036 Uiso 1 1 calc R . . C6G C 0.18067(13) 0.46058(6) 0.29400(14) 0.0343(3) Uani 1 1 d . . . H23A H 0.1195 0.4714 0.3552 0.041 Uiso 1 1 calc R . . H23B H 0.1819 0.4195 0.2879 0.041 Uiso 1 1 calc R . . C7G C 0.36041(13) 0.49378(6) 0.11808(15) 0.0363(3) Uani 1 1 d . . . H33A H 0.4269 0.5200 0.1006 0.044 Uiso 1 1 calc R . . H33B H 0.3496 0.4653 0.0423 0.044 Uiso 1 1 calc R . . C8G C 0.39977(14) 0.46604(6) 0.26246(15) 0.0360(3) Uani 1 1 d . . . H26A H 0.4010 0.4252 0.2508 0.043 Uiso 1 1 calc R . . H26B H 0.4856 0.4783 0.3059 0.043 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 0.0431(6) 0.0501(6) 0.0338(5) 0.0148(4) 0.0122(4) 0.0129(5) C1 0.0264(6) 0.0262(5) 0.0212(5) -0.0029(4) 0.0026(4) 0.0007(4) O2 0.0337(5) 0.0526(6) 0.0341(5) 0.0121(4) 0.0108(4) -0.0017(4) C2 0.0279(6) 0.0287(6) 0.0227(5) -0.0008(4) 0.0040(5) -0.0015(5) O3 0.0328(5) 0.0398(5) 0.0319(5) 0.0079(4) 0.0116(4) 0.0106(4) C3 0.0250(6) 0.0393(7) 0.0371(7) 0.0034(5) 0.0072(5) 0.0001(5) C4 0.0270(7) 0.0410(7) 0.0444(8) 0.0099(6) 0.0011(6) 0.0045(5) C5 0.0427(8) 0.0458(8) 0.0480(9) 0.0205(7) 0.0005(7) -0.0004(7) C6 0.0567(10) 0.0495(9) 0.0443(9) 0.0206(7) 0.0071(8) -0.0065(7) C7 0.0486(9) 0.0408(7) 0.0400(8) 0.0038(6) 0.0177(7) -0.0094(6) C8 0.0360(7) 0.0305(6) 0.0315(6) -0.0013(5) 0.0096(5) -0.0025(5) C9 0.0306(6) 0.0247(5) 0.0224(5) -0.0031(4) 0.0029(5) -0.0042(5) C10 0.0324(7) 0.0308(6) 0.0313(6) 0.0046(5) -0.0002(5) -0.0032(5) C12 0.0339(7) 0.0343(6) 0.0241(6) 0.0012(5) 0.0067(5) -0.0029(5) C18 0.0384(7) 0.0334(6) 0.0239(6) 0.0000(5) 0.0065(5) -0.0003(5) O1A 0.0395(6) 0.0555(6) 0.0360(5) 0.0119(5) -0.0006(4) -0.0027(5) C1A 0.0270(6) 0.0216(5) 0.0289(6) -0.0033(4) 0.0063(5) 0.0015(4) O2A 0.0404(6) 0.0516(6) 0.0281(5) 0.0093(4) 0.0103(4) -0.0036(4) C2A 0.0337(7) 0.0283(6) 0.0230(6) -0.0013(4) 0.0080(5) -0.0015(5) O3A 0.0267(5) 0.0377(5) 0.0410(5) 0.0068(4) 0.0030(4) 0.0027(4) C3A 0.0321(7) 0.0442(7) 0.0286(6) 0.0011(5) 0.0092(5) -0.0096(6) C4A 0.0283(6) 0.0460(7) 0.0296(6) -0.0001(5) 0.0032(5) -0.0058(6) C5A 0.0373(7) 0.0277(6) 0.0313(6) 0.0000(5) 0.0033(5) 0.0021(5) C6A 0.0523(9) 0.0284(6) 0.0353(7) 0.0103(5) 0.0092(6) 0.0005(6) C7A 0.0458(8) 0.0324(7) 0.0486(8) 0.0105(6) 0.0193(7) -0.0045(6) C8A 0.0320(7) 0.0276(6) 0.0436(7) 0.0030(5) 0.0107(6) -0.0015(5) C9A 0.0327(6) 0.0175(5) 0.0285(6) -0.0020(4) 0.0088(5) 0.0013(4) C10A 0.0326(6) 0.0233(5) 0.0277(6) -0.0036(4) 0.0095(5) -0.0010(5) N1G 0.0336(6) 0.0290(5) 0.0224(5) 0.0014(4) 0.0085(4) 0.0000(4) N2G 0.0294(5) 0.0276(5) 0.0232(5) 0.0022(4) 0.0056(4) -0.0003(4) C3G 0.0477(8) 0.0243(6) 0.0327(7) -0.0010(5) 0.0056(6) -0.0025(5) C4G 0.0347(7) 0.0288(6) 0.0280(6) -0.0068(5) 0.0056(5) -0.0014(5) C5G 0.0278(6) 0.0328(6) 0.0289(6) -0.0016(5) 0.0037(5) -0.0018(5) C6G 0.0347(7) 0.0387(7) 0.0295(6) 0.0026(5) 0.0053(5) -0.0126(5) C7G 0.0315(7) 0.0490(8) 0.0314(7) -0.0013(6) 0.0137(6) 0.0046(6) C8G 0.0365(7) 0.0361(7) 0.0382(7) 0.0034(5) 0.0146(6) 0.0109(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 C12 1.2636(17) . ? C1 O3 1.3471(15) . ? C1 C2 1.3883(18) . ? C1 C9 1.4324(16) . ? O2 C12 1.2681(17) . ? C2 C3 1.4117(18) . ? C2 C12 1.4927(17) . ? O3 H11 0.95(2) . ? C3 C4 1.3598(19) . ? C3 H3 0.9500 . ? C4 C10 1.419(2) . ? C4 H4 0.9500 . ? C5 C6 1.363(2) . ? C5 C10 1.4195(19) . ? C5 H5 0.9500 . ? C6 C7 1.403(2) . ? C6 H6 0.9500 . ? C7 C8 1.3705(19) . ? C7 H7 0.9500 . ? C8 C9 1.4121(19) . ? C8 H8 0.9500 . ? C9 C10 1.4174(18) . ? C18 O1A 1.2479(17) . ? C18 O2A 1.2881(17) . ? C18 C2A 1.4836(17) . ? C1A O3A 1.3430(16) . ? C1A C2A 1.3784(18) . ? C1A C9A 1.4345(17) . ? O2A H10A 1.008(10) . ? C2A C3A 1.4249(19) . ? O3A H11A 0.93(2) . ? C3A C4A 1.3538(19) . ? C3A H3A 0.9500 . ? C4A C10A 1.4189(19) . ? C4A H4A 0.9500 . ? C5A C6A 1.363(2) . ? C5A C10A 1.4197(18) . ? C5A H5A 0.9500 . ? C6A C7A 1.400(2) . ? C6A H6A 0.9500 . ? C7A C8A 1.368(2) . ? C7A H7A 0.9500 . ? C8A C9A 1.4132(18) . ? C8A H8A 0.9500 . ? C9A C10A 1.4171(18) . ? N1G C7G 1.4761(17) . ? N1G C3G 1.4784(16) . ? N1G C5G 1.4791(17) . ? N1G H10 0.847(10) . ? N2G C8G 1.4868(17) . ? N2G C6G 1.4872(17) . ? N2G C4G 1.4885(16) . ? N2G H1 0.954(9) . ? C3G C4G 1.5333(19) . ? C3G H31A 0.9900 . ? C3G H31B 0.9900 . ? C4G H25A 0.9900 . ? C4G H25B 0.9900 . ? C5G C6G 1.5322(18) . ? C5G H21A 0.9900 . ? C5G H21B 0.9900 . ? C6G H23A 0.9900 . ? C6G H23B 0.9900 . ? C7G C8G 1.525(2) . ? C7G H33A 0.9900 . ? C7G H33B 0.9900 . ? C8G H26A 0.9900 . ? C8G H26B 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 O3 C1 C2 121.75(11) . . ? O3 C1 C9 117.67(11) . . ? C2 C1 C9 120.58(11) . . ? C1 C2 C3 119.42(11) . . ? C1 C2 C12 119.60(11) . . ? C3 C2 C12 120.98(12) . . ? C1 O3 H11 103.2(13) . . ? C4 C3 C2 121.47(13) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C10 120.32(13) . . ? C3 C4 H4 119.8 . . ? C10 C4 H4 119.8 . . ? C6 C5 C10 120.98(15) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C5 C6 C7 120.72(14) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.15(14) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.29(13) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 119.89(12) . . ? C8 C9 C1 121.71(12) . . ? C10 C9 C1 118.40(12) . . ? C9 C10 C4 119.79(12) . . ? C9 C10 C5 117.97(13) . . ? C4 C10 C5 122.24(13) . . ? O1 C12 O2 123.23(12) . . ? O1 C12 C2 118.15(12) . . ? O2 C12 C2 118.61(12) . . ? O1A C18 O2A 123.32(12) . . ? O1A C18 C2A 119.91(12) . . ? O2A C18 C2A 116.77(12) . . ? O3A C1A C2A 122.33(11) . . ? O3A C1A C9A 117.24(11) . . ? C2A C1A C9A 120.44(12) . . ? C18 O2A H10A 107(2) . . ? C1A C2A C3A 119.60(11) . . ? C1A C2A C18 120.08(12) . . ? C3A C2A C18 120.32(12) . . ? C1A O3A H11A 103.7(14) . . ? C4A C3A C2A 121.21(13) . . ? C4A C3A H3A 119.4 . . ? C2A C3A H3A 119.4 . . ? C3A C4A C10A 120.39(13) . . ? C3A C4A H4A 119.8 . . ? C10A C4A H4A 119.8 . . ? C6A C5A C10A 120.70(13) . . ? C6A C5A H5A 119.6 . . ? C10A C5A H5A 119.6 . . ? C5A C6A C7A 120.65(13) . . ? C5A C6A H6A 119.7 . . ? C7A C6A H6A 119.7 . . ? C8A C7A C6A 120.54(13) . . ? C8A C7A H7A 119.7 . . ? C6A C7A H7A 119.7 . . ? C7A C8A C9A 120.12(13) . . ? C7A C8A H8A 119.9 . . ? C9A C8A H8A 119.9 . . ? C8A C9A C10A 119.69(12) . . ? C8A C9A C1A 121.81(12) . . ? C10A C9A C1A 118.50(11) . . ? C9A C10A C4A 119.83(12) . . ? C9A C10A C5A 118.29(12) . . ? C4A C10A C5A 121.87(12) . . ? C7G N1G C3G 110.06(11) . . ? C7G N1G C5G 110.34(10) . . ? C3G N1G C5G 108.64(10) . . ? C7G N1G H10 112(3) . . ? C3G N1G H10 108(3) . . ? C5G N1G H10 108(3) . . ? C8G N2G C6G 109.86(11) . . ? C8G N2G C4G 110.16(10) . . ? C6G N2G C4G 109.39(10) . . ? C8G N2G H1 108.9(12) . . ? C6G N2G H1 109.1(12) . . ? C4G N2G H1 109.3(11) . . ? N1G C3G C4G 109.65(10) . . ? N1G C3G H31A 109.7 . . ? C4G C3G H31A 109.7 . . ? N1G C3G H31B 109.7 . . ? C4G C3G H31B 109.7 . . ? H31A C3G H31B 108.2 . . ? N2G C4G C3G 108.52(10) . . ? N2G C4G H25A 110.0 . . ? C3G C4G H25A 110.0 . . ? N2G C4G H25B 110.0 . . ? C3G C4G H25B 110.0 . . ? H25A C4G H25B 108.4 . . ? N1G C5G C6G 109.60(10) . . ? N1G C5G H21A 109.8 . . ? C6G C5G H21A 109.8 . . ? N1G C5G H21B 109.8 . . ? C6G C5G H21B 109.8 . . ? H21A C5G H21B 108.2 . . ? N2G C6G C5G 108.65(10) . . ? N2G C6G H23A 110.0 . . ? C5G C6G H23A 110.0 . . ? N2G C6G H23B 110.0 . . ? C5G C6G H23B 110.0 . . ? H23A C6G H23B 108.3 . . ? N1G C7G C8G 109.55(11) . . ? N1G C7G H33A 109.8 . . ? C8G C7G H33A 109.8 . . ? N1G C7G H33B 109.8 . . ? C8G C7G H33B 109.8 . . ? H33A C7G H33B 108.2 . . ? N2G C8G C7G 108.98(11) . . ? N2G C8G H26A 109.9 . . ? C7G C8G H26A 109.9 . . ? N2G C8G H26B 109.9 . . ? C7G C8G H26B 109.9 . . ? H26A C8G H26B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 C1 C2 C3 178.79(11) . . . . ? C9 C1 C2 C3 -0.69(18) . . . . ? O3 C1 C2 C12 -1.35(18) . . . . ? C9 C1 C2 C12 179.18(11) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C12 C2 C3 C4 179.25(13) . . . . ? C2 C3 C4 C10 1.4(2) . . . . ? C10 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C8 -0.4(3) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C10 0.15(19) . . . . ? C7 C8 C9 C1 -179.92(12) . . . . ? O3 C1 C9 C8 2.22(17) . . . . ? C2 C1 C9 C8 -178.29(11) . . . . ? O3 C1 C9 C10 -177.85(11) . . . . ? C2 C1 C9 C10 1.64(17) . . . . ? C8 C9 C10 C4 178.85(12) . . . . ? C1 C9 C10 C4 -1.09(18) . . . . ? C8 C9 C10 C5 -0.59(19) . . . . ? C1 C9 C10 C5 179.47(12) . . . . ? C3 C4 C10 C9 -0.4(2) . . . . ? C3 C4 C10 C5 178.99(14) . . . . ? C6 C5 C10 C9 0.6(2) . . . . ? C6 C5 C10 C4 -178.86(16) . . . . ? C1 C2 C12 O1 0.82(18) . . . . ? C3 C2 C12 O1 -179.32(13) . . . . ? C1 C2 C12 O2 -178.47(12) . . . . ? C3 C2 C12 O2 1.40(19) . . . . ? O3A C1A C2A C3A 178.01(12) . . . . ? C9A C1A C2A C3A -2.15(18) . . . . ? O3A C1A C2A C18 -2.34(18) . . . . ? C9A C1A C2A C18 177.50(11) . . . . ? O1A C18 C2A C1A -1.00(19) . . . . ? O2A C18 C2A C1A 178.86(11) . . . . ? O1A C18 C2A C3A 178.66(13) . . . . ? O2A C18 C2A C3A -1.49(18) . . . . ? C1A C2A C3A C4A 0.4(2) . . . . ? C18 C2A C3A C4A -179.29(13) . . . . ? C2A C3A C4A C10A 1.2(2) . . . . ? C10A C5A C6A C7A -0.1(2) . . . . ? C5A C6A C7A C8A -0.1(2) . . . . ? C6A C7A C8A C9A 0.0(2) . . . . ? C7A C8A C9A C10A 0.19(19) . . . . ? C7A C8A C9A C1A 179.50(12) . . . . ? O3A C1A C9A C8A 2.92(17) . . . . ? C2A C1A C9A C8A -176.93(11) . . . . ? O3A C1A C9A C10A -177.76(10) . . . . ? C2A C1A C9A C10A 2.39(16) . . . . ? C8A C9A C10A C4A 178.46(12) . . . . ? C1A C9A C10A C4A -0.88(17) . . . . ? C8A C9A C10A C5A -0.33(17) . . . . ? C1A C9A C10A C5A -179.67(10) . . . . ? C3A C4A C10A C9A -0.9(2) . . . . ? C3A C4A C10A C5A 177.87(13) . . . . ? C6A C5A C10A C9A 0.28(18) . . . . ? C6A C5A C10A C4A -178.50(13) . . . . ? C7G N1G C3G C4G -57.97(14) . . . . ? C5G N1G C3G C4G 62.94(14) . . . . ? C8G N2G C4G C3G 62.02(14) . . . . ? C6G N2G C4G C3G -58.83(14) . . . . ? N1G C3G C4G N2G -3.45(15) . . . . ? C7G N1G C5G C6G 61.29(14) . . . . ? C3G N1G C5G C6G -59.45(14) . . . . ? C8G N2G C6G C5G -58.73(14) . . . . ? C4G N2G C6G C5G 62.30(14) . . . . ? N1G C5G C6G N2G -2.42(15) . . . . ? C3G N1G C7G C8G 62.12(14) . . . . ? C5G N1G C7G C8G -57.76(14) . . . . ? C6G N2G C8G C7G 62.43(14) . . . . ? C4G N2G C8G C7G -58.14(14) . . . . ? N1G C7G C8G N2G -3.52(16) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.309 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.039 #===END data_c:\H3DABCO _database_code_depnum_ccdc_archive 'CCDC 770710' #TrackingRef 'ALL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-hydroxy-2-naphthoic acid 1,4-diazabicyclo[2.2.2]octane salt ; _chemical_name_common 2C11H8O3.C6H12N2 _chemical_formula_sum 'C28 H28 N2 O6' _chemical_formula_weight 488.52 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 8.6982(17) _cell_length_b 11.373(2) _cell_length_c 11.820(2) _cell_angle_alpha 85.52(3) _cell_angle_beta 81.69(3) _cell_angle_gamma 87.04(3) _cell_volume 1152.5(4) _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 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.100 _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 8875 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.1200 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.56 _reflns_number_total 5102 _reflns_number_gt 2499 _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^)+(0.0491P)^2^+0.7413P] 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 5102 _refine_ls_number_parameters 341 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1777 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.024 _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 0.8836(2) 0.44114(18) 0.21048(17) 0.0315(5) Uani 1 1 d D . . C1 C 0.7561(3) 0.2264(3) 0.2950(2) 0.0266(7) Uani 1 1 d . . . H1 H 0.7281 0.2628 0.2253 0.032 Uiso 1 1 calc R . . O2 O 0.9349(2) 0.47499(19) 0.38461(17) 0.0370(6) Uani 1 1 d . . . C2 C 0.8414(3) 0.2879(3) 0.3582(2) 0.0253(7) Uani 1 1 d . . . O3 O 0.9642(3) 0.2922(2) 0.53012(18) 0.0374(6) Uani 1 1 d . . . C3 C 0.8822(3) 0.2339(3) 0.4629(2) 0.0285(7) Uani 1 1 d . . . C4 C 0.8432(3) 0.1203(3) 0.4982(3) 0.0308(8) Uani 1 1 d . . . H4 H 0.8757 0.0838 0.5663 0.037 Uiso 1 1 calc R . . C5 C 0.7062(4) -0.0581(3) 0.4715(3) 0.0363(8) Uani 1 1 d . . . H5 H 0.7370 -0.0955 0.5398 0.044 Uiso 1 1 calc R . . C6 C 0.6157(4) -0.1159(3) 0.4108(3) 0.0394(9) Uani 1 1 d . . . H6 H 0.5827 -0.1925 0.4381 0.047 Uiso 1 1 calc R . . C7 C 0.5704(4) -0.0635(3) 0.3083(3) 0.0366(8) Uani 1 1 d . . . H7 H 0.5078 -0.1049 0.2666 0.044 Uiso 1 1 calc R . . C8 C 0.6168(3) 0.0471(3) 0.2687(3) 0.0321(8) Uani 1 1 d . . . H8 H 0.5870 0.0818 0.1990 0.039 Uiso 1 1 calc R . . C9 C 0.7090(3) 0.1107(3) 0.3306(2) 0.0259(7) Uani 1 1 d . . . C10 C 0.7548(3) 0.0571(3) 0.4337(2) 0.0283(7) Uani 1 1 d . . . C11 C 0.8898(3) 0.4088(3) 0.3191(3) 0.0291(7) Uani 1 1 d . . . H12 H 0.972(5) 0.368(4) 0.500(4) 0.080(15) Uiso 1 1 d . . . O1A O 1.1362(3) 1.0617(2) 0.2517(2) 0.0473(6) Uani 1 1 d . . . C1A C 1.2719(3) 1.2751(3) 0.2715(2) 0.0284(7) Uani 1 1 d . . . H1A H 1.1990 1.2445 0.3331 0.034 Uiso 1 1 calc R . . O2A O 1.2418(2) 1.05733(19) 0.06918(18) 0.0376(6) Uani 1 1 d . . . C2A C 1.2996(3) 1.2168(3) 0.1729(2) 0.0256(7) Uani 1 1 d . . . O3A O 1.4395(3) 1.2064(2) -0.01873(18) 0.0391(6) Uani 1 1 d . . . C3A C 1.4083(3) 1.2633(3) 0.0804(3) 0.0285(7) Uani 1 1 d . . . C4A C 1.4843(3) 1.3638(3) 0.0901(3) 0.0295(7) Uani 1 1 d . . . H4A H 1.5567 1.3933 0.0276 0.035 Uiso 1 1 calc R . . C5A C 1.5304(3) 1.5299(3) 0.2048(3) 0.0320(8) Uani 1 1 d . . . H5A H 1.6028 1.5619 0.1437 0.038 Uiso 1 1 calc R . . C6A C 1.4987(4) 1.5856(3) 0.3036(3) 0.0375(8) Uani 1 1 d . . . H6A H 1.5487 1.6566 0.3102 0.045 Uiso 1 1 calc R . . C7A C 1.3935(3) 1.5402(3) 0.3960(3) 0.0356(8) Uani 1 1 d . . . H7A H 1.3734 1.5803 0.4645 0.043 Uiso 1 1 calc R . . C8A C 1.3199(3) 1.4387(3) 0.3878(3) 0.0309(8) Uani 1 1 d . . . H8A H 1.2498 1.4077 0.4510 0.037 Uiso 1 1 calc R . . C9A C 1.3479(3) 1.3791(3) 0.2848(2) 0.0264(7) Uani 1 1 d . . . C10A C 1.4566(3) 1.4243(3) 0.1917(3) 0.0272(7) Uani 1 1 d . . . C11A C 1.2187(3) 1.1048(3) 0.1675(3) 0.0305(7) Uani 1 1 d . . . H11A H 1.161(3) 0.9321(16) 0.099(3) 0.057(11) Uiso 1 1 d D . . H12A H 1.364(5) 1.132(4) -0.003(4) 0.096(15) Uiso 1 1 d . . . N1G N 1.1058(3) 0.8499(2) 0.1149(2) 0.0292(6) Uani 1 1 d D . . N2G N 0.9882(3) 0.6498(2) 0.1536(2) 0.0263(6) Uani 1 1 d . . . C3G C 1.1025(4) 0.7959(3) 0.0038(3) 0.0353(8) Uani 1 1 d . . . H35A H 1.2097 0.7763 -0.0323 0.042 Uiso 1 1 calc R . . H35B H 1.0527 0.8521 -0.0495 0.042 Uiso 1 1 calc R . . C4G C 1.0095(4) 0.6834(3) 0.0292(2) 0.0342(8) Uani 1 1 d . . . H31A H 0.9068 0.6973 0.0027 0.041 Uiso 1 1 calc R . . H31B H 1.0657 0.6184 -0.0127 0.041 Uiso 1 1 calc R . . C5G C 1.2022(3) 0.7715(3) 0.1866(3) 0.0291(7) Uani 1 1 d . . . H27A H 1.1949 0.8005 0.2641 0.035 Uiso 1 1 calc R . . H27B H 1.3125 0.7710 0.1512 0.035 Uiso 1 1 calc R . . C6G C 1.1414(3) 0.6474(3) 0.1948(3) 0.0319(8) Uani 1 1 d . . . H36A H 1.2162 0.5959 0.1480 0.038 Uiso 1 1 calc R . . H36B H 1.1312 0.6142 0.2754 0.038 Uiso 1 1 calc R . . C7G C 0.9438(3) 0.8632(3) 0.1766(3) 0.0335(8) Uani 1 1 d . . . H33A H 0.8757 0.9060 0.1256 0.040 Uiso 1 1 calc R . . H33B H 0.9433 0.9087 0.2448 0.040 Uiso 1 1 calc R . . C8G C 0.8847(3) 0.7398(3) 0.2133(3) 0.0300(7) Uani 1 1 d . . . H26A H 0.8812 0.7244 0.2972 0.036 Uiso 1 1 calc R . . H26B H 0.7779 0.7350 0.1947 0.036 Uiso 1 1 calc R . . H11 H 0.929(4) 0.5351(14) 0.188(3) 0.060(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 O1 0.0430(13) 0.0259(13) 0.0260(12) 0.0019(10) -0.0055(9) -0.0074(10) C1 0.0304(16) 0.0257(19) 0.0233(16) 0.0005(14) -0.0041(13) 0.0014(14) O2 0.0513(14) 0.0328(14) 0.0285(12) -0.0061(11) -0.0056(10) -0.0121(11) C2 0.0271(16) 0.0251(18) 0.0234(16) -0.0036(14) -0.0006(13) -0.0023(14) O3 0.0508(15) 0.0354(16) 0.0290(13) -0.0013(12) -0.0132(11) -0.0099(12) C3 0.0325(17) 0.030(2) 0.0229(17) -0.0049(15) -0.0033(13) -0.0013(15) C4 0.0384(18) 0.029(2) 0.0254(17) -0.0029(15) -0.0057(14) 0.0028(15) C5 0.048(2) 0.029(2) 0.0298(18) -0.0016(16) 0.0008(15) -0.0024(16) C6 0.046(2) 0.0242(19) 0.047(2) -0.0042(17) 0.0030(17) -0.0068(16) C7 0.0386(19) 0.027(2) 0.044(2) -0.0042(17) -0.0055(16) -0.0033(16) C8 0.0273(17) 0.034(2) 0.0348(18) -0.0036(16) -0.0047(14) 0.0022(15) C9 0.0251(16) 0.0261(19) 0.0264(17) -0.0020(14) -0.0035(13) -0.0006(14) C10 0.0308(17) 0.0244(19) 0.0279(17) -0.0024(14) 0.0015(14) 0.0015(14) C11 0.0274(17) 0.031(2) 0.0276(18) -0.0027(16) -0.0003(13) 0.0001(14) O1A 0.0566(15) 0.0401(15) 0.0432(15) -0.0025(12) 0.0067(12) -0.0220(12) C1A 0.0289(16) 0.0289(19) 0.0257(17) 0.0060(14) -0.0028(13) -0.0004(14) O2A 0.0486(14) 0.0294(14) 0.0349(13) -0.0028(11) -0.0029(11) -0.0116(11) C2A 0.0263(16) 0.0232(18) 0.0272(17) 0.0023(14) -0.0047(13) -0.0038(13) O3A 0.0472(14) 0.0358(15) 0.0328(13) -0.0068(11) 0.0045(10) -0.0091(12) C3A 0.0318(17) 0.0235(18) 0.0301(18) -0.0012(14) -0.0060(14) 0.0030(14) C4A 0.0260(16) 0.0310(19) 0.0304(17) 0.0024(15) -0.0022(13) -0.0019(14) C5A 0.0309(17) 0.028(2) 0.0374(19) 0.0004(15) -0.0050(14) -0.0073(15) C6A 0.0367(19) 0.034(2) 0.043(2) -0.0041(17) -0.0087(16) -0.0065(16) C7A 0.0332(18) 0.038(2) 0.038(2) -0.0101(17) -0.0112(15) 0.0026(16) C8A 0.0308(17) 0.035(2) 0.0262(17) 0.0011(15) -0.0036(13) 0.0006(15) C9A 0.0264(16) 0.0242(18) 0.0290(17) 0.0013(14) -0.0075(13) 0.0014(14) C10A 0.0247(16) 0.0271(19) 0.0300(17) -0.0004(14) -0.0071(13) 0.0035(14) C11A 0.0304(17) 0.0246(19) 0.036(2) 0.0033(16) -0.0051(15) -0.0026(15) N1G 0.0294(14) 0.0270(16) 0.0310(15) -0.0020(12) -0.0021(11) -0.0049(12) N2G 0.0313(14) 0.0225(15) 0.0249(14) -0.0002(11) -0.0038(11) -0.0020(11) C3G 0.0412(19) 0.038(2) 0.0265(18) 0.0012(15) -0.0048(14) -0.0039(16) C4G 0.047(2) 0.031(2) 0.0246(17) -0.0010(15) -0.0058(14) -0.0051(16) C5G 0.0268(16) 0.031(2) 0.0297(17) 0.0008(15) -0.0070(13) -0.0039(14) C6G 0.0318(17) 0.029(2) 0.0339(18) 0.0021(15) -0.0053(14) 0.0001(15) C7G 0.0283(17) 0.031(2) 0.0404(19) -0.0056(16) 0.0010(14) -0.0016(15) C8G 0.0279(16) 0.0276(19) 0.0333(18) -0.0015(15) -0.0004(13) -0.0029(14) _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 C11 1.316(3) . ? O1 H11 1.156(10) . ? C1 C2 1.376(4) . ? C1 C9 1.413(4) . ? C1 H1 0.9500 . ? O2 C11 1.237(3) . ? C2 C3 1.421(4) . ? C2 C11 1.478(4) . ? O3 C3 1.370(3) . ? O3 H12 0.91(4) . ? C3 C4 1.370(4) . ? C4 C10 1.414(4) . ? C4 H4 0.9500 . ? C5 C6 1.362(4) . ? C5 C10 1.416(4) . ? C5 H5 0.9500 . ? C6 C7 1.407(5) . ? C6 H6 0.9500 . ? C7 C8 1.367(4) . ? C7 H7 0.9500 . ? C8 C9 1.419(4) . ? C8 H8 0.9500 . ? C9 C10 1.420(4) . ? O1A C11A 1.225(4) . ? C1A C2A 1.371(4) . ? C1A C9A 1.415(4) . ? C1A H1A 0.9500 . ? O2A C11A 1.304(3) . ? C2A C3A 1.426(4) . ? C2A C11A 1.497(4) . ? O3A C3A 1.368(3) . ? O3A H12A 1.09(5) . ? C3A C4A 1.370(4) . ? C4A C10A 1.415(4) . ? C4A H4A 0.9500 . ? C5A C6A 1.359(4) . ? C5A C10A 1.419(4) . ? C5A H5A 0.9500 . ? C6A C7A 1.403(5) . ? C6A H6A 0.9500 . ? C7A C8A 1.366(4) . ? C7A H7A 0.9500 . ? C8A C9A 1.424(4) . ? C8A H8A 0.9500 . ? C9A C10A 1.425(4) . ? N1G C5G 1.492(4) . ? N1G C7G 1.496(4) . ? N1G C3G 1.498(4) . ? N1G H11A 1.062(10) . ? N2G C4G 1.477(4) . ? N2G C8G 1.480(3) . ? N2G C6G 1.482(4) . ? N2G H11 1.434(11) . ? C3G C4G 1.535(4) . ? C3G H35A 0.9900 . ? C3G H35B 0.9900 . ? C4G H31A 0.9900 . ? C4G H31B 0.9900 . ? C5G C6G 1.524(4) . ? C5G H27A 0.9900 . ? C5G H27B 0.9900 . ? C6G H36A 0.9900 . ? C6G H36B 0.9900 . ? C7G C8G 1.528(4) . ? C7G H33A 0.9900 . ? C7G H33B 0.9900 . ? C8G H26A 0.9900 . ? C8G H26B 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 C11 O1 H11 110.7(16) . . ? C2 C1 C9 121.9(3) . . ? C2 C1 H1 119.0 . . ? C9 C1 H1 119.0 . . ? C1 C2 C3 119.1(3) . . ? C1 C2 C11 121.0(3) . . ? C3 C2 C11 119.9(3) . . ? C3 O3 H12 108(3) . . ? O3 C3 C4 118.0(3) . . ? O3 C3 C2 121.3(3) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C10 120.4(3) . . ? C3 C4 H4 119.8 . . ? C10 C4 H4 119.8 . . ? C6 C5 C10 120.7(3) . . ? C6 C5 H5 119.6 . . ? C10 C5 H5 119.6 . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.8(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C1 C9 C8 122.9(3) . . ? C1 C9 C10 118.1(3) . . ? C8 C9 C10 119.0(3) . . ? C4 C10 C5 121.4(3) . . ? C4 C10 C9 119.8(3) . . ? C5 C10 C9 118.7(3) . . ? O2 C11 O1 122.1(3) . . ? O2 C11 C2 121.8(3) . . ? O1 C11 C2 116.1(3) . . ? C2A C1A C9A 122.4(3) . . ? C2A C1A H1A 118.8 . . ? C9A C1A H1A 118.8 . . ? C1A C2A C3A 118.7(3) . . ? C1A C2A C11A 119.0(3) . . ? C3A C2A C11A 122.3(3) . . ? C3A O3A H12A 104(2) . . ? O3A C3A C4A 119.3(3) . . ? O3A C3A C2A 120.0(3) . . ? C4A C3A C2A 120.7(3) . . ? C3A C4A C10A 121.0(3) . . ? C3A C4A H4A 119.5 . . ? C10A C4A H4A 119.5 . . ? C6A C5A C10A 120.9(3) . . ? C6A C5A H5A 119.6 . . ? C10A C5A H5A 119.6 . . ? C5A C6A C7A 121.1(3) . . ? C5A C6A H6A 119.4 . . ? C7A C6A H6A 119.4 . . ? C8A C7A C6A 120.2(3) . . ? C8A C7A H7A 119.9 . . ? C6A C7A H7A 119.9 . . ? C7A C8A C9A 120.2(3) . . ? C7A C8A H8A 119.9 . . ? C9A C8A H8A 119.9 . . ? C1A C9A C8A 122.2(3) . . ? C1A C9A C10A 118.3(3) . . ? C8A C9A C10A 119.5(3) . . ? C4A C10A C5A 123.0(3) . . ? C4A C10A C9A 119.0(3) . . ? C5A C10A C9A 118.0(3) . . ? O1A C11A O2A 123.0(3) . . ? O1A C11A C2A 120.8(3) . . ? O2A C11A C2A 116.2(3) . . ? C5G N1G C7G 109.7(2) . . ? C5G N1G C3G 108.9(2) . . ? C7G N1G C3G 109.6(2) . . ? C5G N1G H11A 106.9(18) . . ? C7G N1G H11A 111.9(17) . . ? C3G N1G H11A 109.8(18) . . ? C4G N2G C8G 108.9(2) . . ? C4G N2G C6G 108.8(2) . . ? C8G N2G C6G 108.7(2) . . ? C4G N2G H11 115.9(13) . . ? C8G N2G H11 109.1(13) . . ? C6G N2G H11 105.2(13) . . ? N1G C3G C4G 108.0(2) . . ? N1G C3G H35A 110.1 . . ? C4G C3G H35A 110.1 . . ? N1G C3G H35B 110.1 . . ? C4G C3G H35B 110.1 . . ? H35A C3G H35B 108.4 . . ? N2G C4G C3G 109.9(2) . . ? N2G C4G H31A 109.7 . . ? C3G C4G H31A 109.7 . . ? N2G C4G H31B 109.7 . . ? C3G C4G H31B 109.7 . . ? H31A C4G H31B 108.2 . . ? N1G C5G C6G 108.1(2) . . ? N1G C5G H27A 110.1 . . ? C6G C5G H27A 110.1 . . ? N1G C5G H27B 110.1 . . ? C6G C5G H27B 110.1 . . ? H27A C5G H27B 108.4 . . ? N2G C6G C5G 110.4(2) . . ? N2G C6G H36A 109.6 . . ? C5G C6G H36A 109.6 . . ? N2G C6G H36B 109.6 . . ? C5G C6G H36B 109.6 . . ? H36A C6G H36B 108.1 . . ? N1G C7G C8G 108.1(2) . . ? N1G C7G H33A 110.1 . . ? C8G C7G H33A 110.1 . . ? N1G C7G H33B 110.1 . . ? C8G C7G H33B 110.1 . . ? H33A C7G H33B 108.4 . . ? N2G C8G C7G 110.2(2) . . ? N2G C8G H26A 109.6 . . ? C7G C8G H26A 109.6 . . ? N2G C8G H26B 109.6 . . ? C7G C8G H26B 109.6 . . ? H26A C8G H26B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -0.6(4) . . . . ? C9 C1 C2 C11 179.8(2) . . . . ? C1 C2 C3 O3 -178.7(2) . . . . ? C11 C2 C3 O3 0.9(4) . . . . ? C1 C2 C3 C4 2.8(4) . . . . ? C11 C2 C3 C4 -177.6(3) . . . . ? O3 C3 C4 C10 178.2(2) . . . . ? C2 C3 C4 C10 -3.2(4) . . . . ? C10 C5 C6 C7 1.1(5) . . . . ? C5 C6 C7 C8 -0.3(5) . . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? C2 C1 C9 C8 177.9(3) . . . . ? C2 C1 C9 C10 -1.2(4) . . . . ? C7 C8 C9 C1 -178.2(3) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? C3 C4 C10 C5 -176.7(3) . . . . ? C3 C4 C10 C9 1.4(4) . . . . ? C6 C5 C10 C4 177.3(3) . . . . ? C6 C5 C10 C9 -0.8(4) . . . . ? C1 C9 C10 C4 0.8(4) . . . . ? C8 C9 C10 C4 -178.3(3) . . . . ? C1 C9 C10 C5 178.9(2) . . . . ? C8 C9 C10 C5 -0.2(4) . . . . ? C1 C2 C11 O2 163.5(3) . . . . ? C3 C2 C11 O2 -16.0(4) . . . . ? C1 C2 C11 O1 -17.2(4) . . . . ? C3 C2 C11 O1 163.3(2) . . . . ? C9A C1A C2A C3A -0.3(4) . . . . ? C9A C1A C2A C11A 177.7(3) . . . . ? C1A C2A C3A O3A 179.4(2) . . . . ? C11A C2A C3A O3A 1.4(4) . . . . ? C1A C2A C3A C4A 0.3(4) . . . . ? C11A C2A C3A C4A -177.6(3) . . . . ? O3A C3A C4A C10A -179.3(3) . . . . ? C2A C3A C4A C10A -0.2(4) . . . . ? C10A C5A C6A C7A 0.6(5) . . . . ? C5A C6A C7A C8A -0.4(5) . . . . ? C6A C7A C8A C9A -0.9(4) . . . . ? C2A C1A C9A C8A -179.4(3) . . . . ? C2A C1A C9A C10A 0.2(4) . . . . ? C7A C8A C9A C1A -178.6(3) . . . . ? C7A C8A C9A C10A 1.8(4) . . . . ? C3A C4A C10A C5A -178.8(3) . . . . ? C3A C4A C10A C9A 0.1(4) . . . . ? C6A C5A C10A C4A 179.3(3) . . . . ? C6A C5A C10A C9A 0.3(4) . . . . ? C1A C9A C10A C4A -0.1(4) . . . . ? C8A C9A C10A C4A 179.5(3) . . . . ? C1A C9A C10A C5A 178.9(3) . . . . ? C8A C9A C10A C5A -1.5(4) . . . . ? C1A C2A C11A O1A -4.3(4) . . . . ? C3A C2A C11A O1A 173.6(3) . . . . ? C1A C2A C11A O2A 175.7(3) . . . . ? C3A C2A C11A O2A -6.3(4) . . . . ? C5G N1G C3G C4G 68.3(3) . . . . ? C7G N1G C3G C4G -51.7(3) . . . . ? C8G N2G C4G C3G 67.5(3) . . . . ? C6G N2G C4G C3G -50.7(3) . . . . ? N1G C3G C4G N2G -13.9(3) . . . . ? C7G N1G C5G C6G 67.4(3) . . . . ? C3G N1G C5G C6G -52.6(3) . . . . ? C4G N2G C6G C5G 67.1(3) . . . . ? C8G N2G C6G C5G -51.3(3) . . . . ? N1G C5G C6G N2G -13.0(3) . . . . ? C5G N1G C7G C8G -52.1(3) . . . . ? C3G N1G C7G C8G 67.5(3) . . . . ? C4G N2G C8G C7G -51.4(3) . . . . ? C6G N2G C8G C7G 66.9(3) . . . . ? N1G C7G C8G N2G -13.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.245 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.064 #===END