# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 loop_ _publ_author_name _publ_author_address C.D.Antoniadis ; Section of Inorganic and Analytical Chemistry Department of Chemistry University of Ioannina 45110 Ioannina Greece ; S.K.Hadjikakou ; Section of Inorganic and Analytical Chemistry Department of Chemistry University of Ioannina 45110 Ioannina Greece ; N.Hadjiliadis ; Section of Inorganic and Analytical Chemistry Department of Chemistry University of Ioannina 45110 Ioannina Greece ; M.Kubicki ; Department of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Poznan Poland ; ; I.S.Butler ; ; Department of Chemistry McGill University 801 Sherbrooke, Montreal Quebec Canada H2A 2K6 ; _publ_contact_author_name 'ProfD Nick Hadjiliadis' _publ_contact_author_address ; Department of Chemistry University of Ioannina University Campus Ioannina 45110 GREECE ; _publ_contact_author_email NHADJIS@CC.UOI.GR _publ_section_title ; Synthesis, X-ray characterization and study of new ionic complexes of 2-pyridone, obtained by oxidation with I2. ; data_1 _database_code_depnum_ccdc_archive 'CCDC 230098' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tris(2-hydroxypyridine)-2-hydroxypyridinium triiodide ; _chemical_name_common 'tris(2-hydroxypyridine)-2-hydroxypyridinium triiodide' _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 N2 O2, 2(C5 H5 N O), I3' _chemical_formula_sum 'C20 H21 I3 N4 O4' _chemical_formula_weight 762.11 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' I I -0.4742 1.8119 '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 _symmetry_space_group_name_Hall '-C 2yc' 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 14.0652(11) _cell_length_b 15.6176(14) _cell_length_c 11.5015(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.635(7) _cell_angle_gamma 90.00 _cell_volume 2490.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 2983 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.032 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 3.797 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.529 _exptl_absorpt_correction_T_max 0.827 _exptl_absorpt_process_details 'SORTAV (Blessing, 1989)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(1) _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 'KUMA KM4CCD four-circle diffractometer' _diffrn_measurement_method '\w scan' _diffrn_reflns_number 8005 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 29.35 _reflns_number_total 3130 _reflns_number_gt 2150 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD v.169 (Oxford Diffraction, 2002a)' _computing_cell_refinement 'CrysAlisCCD v.169 (Oxford Diffraction, 2002a)' _computing_data_reduction 'CrysAlisRed v.169 (Oxford Diffraction, 2002b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3130 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _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 I1 I 0.5000 0.5000 0.5000 0.02633(15) Uani 1 2 d S . . I2 I 0.49688(3) 0.68493(3) 0.53228(4) 0.03340(14) Uani 1 1 d . . . N1A N 0.6779(3) 0.8653(3) 0.5920(4) 0.0234(10) Uani 1 1 d . . . H1A H 0.6503 0.8873 0.5243 0.028 Uiso 1 1 calc R . . C2A C 0.6256(4) 0.8611(3) 0.6816(4) 0.0205(11) Uani 1 1 d . . . O2A O 0.5399(3) 0.8913(2) 0.6632(3) 0.0235(8) Uani 1 1 d . . . H2A H 0.5146 0.8844 0.7238 0.028 Uiso 0.50 1 calc PR . . C3A C 0.6722(4) 0.8224(3) 0.7875(5) 0.0245(12) Uani 1 1 d . . . H3A H 0.6383 0.8150 0.8516 0.029 Uiso 1 1 calc R . . C4A C 0.7653(4) 0.7957(4) 0.7974(5) 0.0291(13) Uani 1 1 d . . . H4A H 0.7965 0.7717 0.8697 0.035 Uiso 1 1 calc R . . C5A C 0.8157(4) 0.8032(4) 0.7031(5) 0.0331(14) Uani 1 1 d . . . H5A H 0.8807 0.7846 0.7101 0.040 Uiso 1 1 calc R . . C6A C 0.7692(4) 0.8375(4) 0.6014(5) 0.0277(13) Uani 1 1 d . . . H6A H 0.8016 0.8421 0.5356 0.033 Uiso 1 1 calc R . . N1B N 0.5989(3) 0.9182(3) 0.1694(3) 0.0214(10) Uani 1 1 d . . . H1B H 0.5357 0.9139 0.1596 0.026 Uiso 1 1 calc R . . C2B C 0.6496(4) 0.9241(3) 0.2816(4) 0.0233(12) Uani 1 1 d . . . O2B O 0.6014(3) 0.9207(3) 0.3668(3) 0.0268(9) Uani 1 1 d . . . C3B C 0.7504(4) 0.9324(4) 0.2926(5) 0.0254(12) Uani 1 1 d . . . H3B H 0.7882 0.9390 0.3686 0.031 Uiso 1 1 calc R . . C4B C 0.7945(4) 0.9310(4) 0.1959(5) 0.0275(12) Uani 1 1 d . . . H4B H 0.8628 0.9343 0.2053 0.033 Uiso 1 1 calc R . . C5B C 0.7396(4) 0.9247(4) 0.0821(5) 0.0284(13) Uani 1 1 d . . . H5B H 0.7699 0.9247 0.0142 0.034 Uiso 1 1 calc R . . C6B C 0.6429(4) 0.9188(4) 0.0717(4) 0.0252(12) Uani 1 1 d . . . H6B H 0.6048 0.9149 -0.0045 0.030 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 I1 0.0187(3) 0.0302(3) 0.0297(3) -0.0103(2) 0.00294(19) -0.0017(2) I2 0.0252(2) 0.0296(2) 0.0456(3) -0.01160(16) 0.00651(16) -0.00179(17) N1A 0.024(2) 0.031(3) 0.017(2) 0.0019(19) 0.0054(17) -0.003(2) C2A 0.019(3) 0.020(3) 0.022(3) -0.003(2) 0.002(2) -0.006(2) O2A 0.022(2) 0.029(2) 0.0184(18) 0.0002(14) 0.0023(14) -0.0023(16) C3A 0.028(3) 0.026(3) 0.018(3) 0.004(2) 0.002(2) 0.000(2) C4A 0.030(3) 0.033(3) 0.023(3) 0.007(2) 0.000(2) 0.003(3) C5A 0.026(3) 0.036(4) 0.036(3) 0.004(3) 0.001(2) 0.003(3) C6A 0.022(3) 0.035(3) 0.028(3) 0.002(2) 0.008(2) -0.002(2) N1B 0.017(2) 0.032(3) 0.015(2) 0.0019(17) -0.0001(17) 0.0001(19) C2B 0.026(3) 0.025(3) 0.017(3) -0.001(2) 0.000(2) 0.000(2) O2B 0.020(2) 0.045(3) 0.0149(18) -0.0008(15) 0.0018(15) 0.0017(17) C3B 0.024(3) 0.035(3) 0.015(2) -0.002(2) -0.003(2) 0.000(3) C4B 0.025(3) 0.028(3) 0.029(3) -0.001(2) 0.002(2) -0.004(2) C5B 0.030(3) 0.039(3) 0.017(3) 0.003(2) 0.009(2) -0.001(3) C6B 0.031(3) 0.033(3) 0.011(2) 0.000(2) 0.002(2) -0.001(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 I1 I2 2.9132(5) 5_666 ? I1 I2 2.9132(5) . ? N1A C6A 1.341(7) . ? N1A C2A 1.365(6) . ? N1A H1A 0.8800 . ? C2A O2A 1.278(6) . ? C2A C3A 1.419(7) . ? O2A H2A 0.8400 . ? C3A C4A 1.361(8) . ? C3A H3A 0.9500 . ? C4A C5A 1.397(8) . ? C4A H4A 0.9500 . ? C5A C6A 1.352(8) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? N1B C2B 1.369(7) . ? N1B C6B 1.371(7) . ? N1B H1B 0.8800 . ? C2B O2B 1.282(6) . ? C2B C3B 1.408(8) . ? C3B C4B 1.361(8) . ? C3B H3B 0.9500 . ? C4B C5B 1.408(8) . ? C4B H4B 0.9500 . ? C5B C6B 1.347(8) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 I1 I2 180.0 5_666 . ? C6A N1A C2A 123.6(5) . . ? C6A N1A H1A 118.2 . . ? C2A N1A H1A 118.2 . . ? O2A C2A N1A 118.1(5) . . ? O2A C2A C3A 125.9(5) . . ? N1A C2A C3A 116.0(5) . . ? C2A O2A H2A 109.5 . . ? C4A C3A C2A 120.2(5) . . ? C4A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 . . ? C3A C4A C5A 121.0(5) . . ? C3A C4A H4A 119.5 . . ? C5A C4A H4A 119.5 . . ? C6A C5A C4A 118.0(6) . . ? C6A C5A H5A 121.0 . . ? C4A C5A H5A 121.0 . . ? N1A C6A C5A 121.1(5) . . ? N1A C6A H6A 119.5 . . ? C5A C6A H6A 119.5 . . ? C2B N1B C6B 122.5(5) . . ? C2B N1B H1B 118.8 . . ? C6B N1B H1B 118.8 . . ? O2B C2B N1B 117.3(5) . . ? O2B C2B C3B 126.0(5) . . ? N1B C2B C3B 116.6(5) . . ? C4B C3B C2B 121.0(5) . . ? C4B C3B H3B 119.5 . . ? C2B C3B H3B 119.5 . . ? C3B C4B C5B 120.4(5) . . ? C3B C4B H4B 119.8 . . ? C5B C4B H4B 119.8 . . ? C6B C5B C4B 118.4(5) . . ? C6B C5B H5B 120.8 . . ? C4B C5B H5B 120.8 . . ? C5B C6B N1B 121.0(5) . . ? C5B C6B H6B 119.5 . . ? N1B C6B H6B 119.5 . . ? 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 N1A H1A O2B 0.88 1.90 2.772(5) 170.6 . O2A H2A O2A 0.84 1.62 2.449(7) 168.4 2_656 C3A H3A I2 0.95 3.22 4.026(6) 143.7 2_656 C4A H4A I2 0.95 3.18 3.880(6) 131.6 8_566 C6A H6A I2 0.95 3.09 3.874(6) 140.7 7_666 N1B H1B O2B 0.88 1.90 2.778(6) 172.2 2_655 C3B H3B I1 0.95 3.25 4.041(5) 142.0 3 C4B H4B I1 0.95 3.45 4.095(6) 127.6 4_655 C5B H5B I1 0.95 3.47 4.105(6) 126.1 4_655 C6B H6B O2A 0.95 2.52 3.430(6) 160.0 2_655 _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.178 _refine_diff_density_min -1.816 _refine_diff_density_rms 0.238 data_2 _database_code_depnum_ccdc_archive 'CCDC 230099' _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexakis(2-hydroxypyridine)-bis(2-hydroxypyridinium) di-heptaiodide diiodine iodate ; _chemical_name_common ; hexakis(2-hydroxypyridine)-bis(2-hydroxypyridinium) di- heptaiodide diiodine iodate ; _chemical_melting_point ? _chemical_formula_moiety ; 2(C10 H11 N2 O2), 4(C5 H5 N O), 1.5(I7), 0.5(I5) ; _chemical_formula_sum 'C40 H42 I13 N8 O8' _chemical_formula_weight 2412.52 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' I I -0.4742 1.8119 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2119(16) _cell_length_b 12.6039(18) _cell_length_c 23.715(3) _cell_angle_alpha 78.545(12) _cell_angle_beta 76.688(12) _cell_angle_gamma 86.422(12) _cell_volume 3195.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2420 _cell_measurement_theta_min 3 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2182 _exptl_absorpt_coefficient_mu 6.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.32 _exptl_absorpt_correction_T_max 0.53 _exptl_absorpt_process_details 'SORTAV (Blessing, 1989)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'KUMA KM4CCD four-circle diffractometer' _diffrn_measurement_method '\w scan' _diffrn_reflns_number 26516 _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_sigmaI/netI 0.1829 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11040 _reflns_number_gt 3319 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisCCD v.169 (Oxford Diffraction, 2002a)' _computing_cell_refinement 'CrysAlisCCD v.169 (Oxford Diffraction, 2002a)' _computing_data_reduction 'CrysAlisRed v.169 (Oxford Diffraction, 2002b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 11040 _refine_ls_number_parameters 625 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.2058 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1576 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 0.772 _refine_ls_restrained_S_all 0.771 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.0000 0.0000 0.0000 0.0763(7) Uani 1 2 d S . . I2 I 0.07589(15) 0.10564(11) 0.08600(8) 0.0869(5) Uani 1 1 d . . . I3 I 0.00283(13) -0.09816(11) 0.18882(6) 0.0672(4) Uani 1 1 d . . . I4 I -0.05453(14) -0.28797(11) 0.27136(7) 0.0769(5) Uani 1 1 d . . . I5 I 0.39582(14) 0.38774(11) 0.39640(8) 0.0925(6) Uani 1 1 d . . . I6 I 0.30716(13) 0.31402(11) 0.31050(8) 0.0860(6) Uani 1 1 d . . . I7 I 0.18291(13) 0.21471(12) 0.21768(8) 0.0893(6) Uani 1 1 d . . . I8 I 0.42342(13) 0.13023(10) 0.16822(6) 0.0652(4) Uani 1 1 d . . . I9 I 0.66796(13) 0.04526(11) 0.12138(6) 0.0686(4) Uani 1 1 d . . . I10 I 0.57775(13) -0.18034(11) 0.21617(6) 0.0685(4) Uani 1 1 d . . . I11 I 0.50245(14) -0.36844(11) 0.29541(7) 0.0768(5) Uani 1 1 d . . . I12 I 0.5000 0.5000 0.5000 0.1035(9) Uani 1 2 d S . . I13 I 0.75930(17) 0.46359(12) 0.40473(9) 0.1035(6) Uani 1 1 d . . . I14 I 0.99334(16) 0.41113(12) 0.34684(7) 0.0918(6) Uani 1 1 d . . . N1A N 0.8181(13) 0.3601(9) 0.1185(6) 0.040(4) Uani 1 1 d U . . H1A H 0.8386 0.3459 0.0834 0.048 Uiso 1 1 d R . . C2A C 0.9044(18) 0.3946(13) 0.1390(10) 0.046(5) Uani 1 1 d U . . O2A O 1.0125(10) 0.4155(8) 0.1047(6) 0.053(3) Uani 1 1 d . . . C3A C 0.8706(17) 0.4144(16) 0.1973(9) 0.068(6) Uani 1 1 d . . . H3A H 0.9288 0.4474 0.2101 0.082 Uiso 1 1 d R . . C4A C 0.755(2) 0.4012(14) 0.2267(9) 0.062(6) Uani 1 1 d U . . H4A H 0.7348 0.4134 0.2652 0.074 Uiso 1 1 d R . . C5A C 0.6647(19) 0.3625(17) 0.2034(9) 0.073(7) Uani 1 1 d . . . H5A H 0.5830 0.3585 0.2236 0.088 Uiso 1 1 d R . . C6A C 0.7005(16) 0.3452(13) 0.1478(10) 0.056(6) Uani 1 1 d . . . H6BA H 0.6465 0.3075 0.1349 0.067 Uiso 1 1 d R . . N1B N 0.2190(14) 0.4926(11) 0.1276(7) 0.050(4) Uani 1 1 d . . . H1B H 0.1595 0.4637 0.1193 0.060 Uiso 1 1 d R . . C2B C 0.3303(19) 0.4669(15) 0.1012(9) 0.049(5) Uani 1 1 d U . . O2B O 0.3474(10) 0.4090(9) 0.0616(6) 0.064(4) Uani 1 1 d . . . H2B H 0.4209 0.4049 0.0470 0.076 Uiso 0.50 1 calc PR . . C3B C 0.4251(17) 0.5172(15) 0.1174(9) 0.059(6) Uani 1 1 d U . . H3B H 0.5063 0.4939 0.1083 0.071 Uiso 1 1 d R . . C4B C 0.403(2) 0.5797(18) 0.1562(11) 0.088(7) Uani 1 1 d U . . H4B H 0.4663 0.6233 0.1576 0.105 Uiso 1 1 d R . . C5B C 0.2781(19) 0.6021(16) 0.1858(10) 0.082(7) Uani 1 1 d . . . H5B H 0.2588 0.6434 0.2152 0.098 Uiso 1 1 d R . . C6B C 0.1906(18) 0.5592(16) 0.1661(9) 0.061(6) Uani 1 1 d . . . H6B H 0.1092 0.5698 0.1842 0.073 Uiso 1 1 d R . . N1C N 0.6845(13) 0.2408(11) 0.9756(6) 0.048(4) Uani 1 1 d . . . H1C H 0.7453 0.2760 0.9783 0.057 Uiso 1 1 d R . . C2C C 0.5694(16) 0.2701(13) 1.0021(8) 0.037(5) Uani 1 1 d . . . O2C O 0.5591(10) 0.3501(9) 1.0294(5) 0.051(3) Uani 1 1 d . . . H2C H 0.4851 0.3590 1.0409 0.061 Uiso 0.50 1 d PR . . C3C C 0.4667(17) 0.2198(14) 0.9930(8) 0.055(6) Uani 1 1 d . . . H3C H 0.3868 0.2356 1.0112 0.066 Uiso 1 1 d R . . C4C C 0.4939(19) 0.1390(14) 0.9626(9) 0.058(6) Uani 1 1 d . . . H4C H 0.4272 0.1042 0.9577 0.070 Uiso 1 1 d R . . C5C C 0.615(2) 0.1126(16) 0.9313(10) 0.076(7) Uani 1 1 d . . . H5C H 0.6227 0.0602 0.9081 0.092 Uiso 1 1 d R . . C6C C 0.7060(17) 0.1621(15) 0.9460(8) 0.052(5) Uani 1 1 d . . . H6C H 0.7848 0.1437 0.9275 0.062 Uiso 1 1 d R . . N1D N 0.0725(13) 0.3768(10) 0.9916(6) 0.041(4) Uani 1 1 d . . . H1D H 0.0510 0.3962 1.0254 0.049 Uiso 1 1 d R . . C2D C -0.018(2) 0.3403(14) 0.9689(9) 0.051(5) Uani 1 1 d . . . O2D O -0.1232(12) 0.3372(10) 0.9977(5) 0.060(4) Uani 1 1 d . . . C3D C 0.0245(18) 0.3053(14) 0.9138(9) 0.057(5) Uani 1 1 d U . . H3D H -0.0329 0.2703 0.9016 0.068 Uiso 1 1 d R . . C4D C 0.1432(18) 0.3094(17) 0.8869(9) 0.071(6) Uani 1 1 d . . . H4D H 0.1642 0.2992 0.8481 0.086 Uiso 1 1 d R . . C5D C 0.232(2) 0.3540(17) 0.9081(11) 0.085(7) Uani 1 1 d U . . H5D H 0.3141 0.3393 0.8938 0.102 Uiso 1 1 d R . . C6D C 0.1874(19) 0.3827(14) 0.9644(9) 0.057(5) Uani 1 1 d U . . H6D H 0.2424 0.4193 0.9772 0.068 Uiso 1 1 d R . . N1E N 0.6745(14) 0.1351(12) 0.3845(7) 0.051(4) Uani 1 1 d . . . H1E H 0.6566 0.1407 0.4211 0.080 Uiso 1 1 d R . . C2E C 0.5887(18) 0.1065(13) 0.3630(9) 0.040(5) Uani 1 1 d . . . O2E O 0.4832(11) 0.0844(9) 0.3953(5) 0.047(3) Uani 1 1 d . . . C3E C 0.6239(18) 0.0861(13) 0.3027(9) 0.051(5) Uani 1 1 d . . . H3E H 0.5701 0.0517 0.2880 0.062 Uiso 1 1 d R . . C4E C 0.742(2) 0.1061(15) 0.2758(9) 0.066(6) Uani 1 1 d U . . H4E H 0.7631 0.1089 0.2353 0.079 Uiso 1 1 d R . . C5E C 0.8326(18) 0.1365(16) 0.2973(10) 0.068(6) Uani 1 1 d . . . H5E H 0.9136 0.1493 0.2774 0.081 Uiso 1 1 d R . . C6E C 0.791(2) 0.1557(14) 0.3536(11) 0.066(6) Uani 1 1 d . . . H6E H 0.8510 0.1644 0.3733 0.080 Uiso 1 1 d R . . N1F N 0.2821(13) 0.0129(10) 0.3699(7) 0.044(4) Uani 1 1 d . . . H1F H 0.3415 0.0403 0.3791 0.080 Uiso 1 1 d R . . C2F C 0.166(2) 0.0341(15) 0.3975(9) 0.053(5) Uani 1 1 d . . . O2F O 0.1493(10) 0.0942(10) 0.4357(6) 0.056(4) Uani 1 1 d . . . H2F H 0.0905 0.1355 0.4324 0.067 Uiso 0.50 1 d PR . . C3F C 0.0700(16) -0.0123(14) 0.3810(9) 0.049(5) Uani 1 1 d . . . H3F H -0.0101 -0.0109 0.4030 0.059 Uiso 1 1 d R . . C4F C 0.101(2) -0.0798(16) 0.3410(10) 0.069(6) Uani 1 1 d . . . H4F H 0.0389 -0.1031 0.3264 0.082 Uiso 1 1 d R . . C5F C 0.224(2) -0.0961(15) 0.3129(9) 0.066(6) Uani 1 1 d . . . H5F H 0.2437 -0.1430 0.2863 0.079 Uiso 1 1 d R . . C6F C 0.3075(18) -0.0498(15) 0.3291(9) 0.054(5) Uani 1 1 d U . . H6F H 0.3879 -0.0560 0.3083 0.065 Uiso 1 1 d R . . N1G N 0.8140(14) 0.2480(11) 0.5294(6) 0.041(4) Uani 1 1 d . . . H1G H 0.7541 0.2104 0.5278 0.049 Uiso 1 1 d R . . C2G C 0.9249(17) 0.2222(15) 0.5014(8) 0.040(5) Uani 1 1 d . . . O2G O 0.9360(10) 0.1488(9) 0.4711(6) 0.058(4) Uani 1 1 d . . . H2G H 1.0089 0.1341 0.4595 0.080 Uiso 0.50 1 d PR . . C3G C 1.0202(19) 0.2792(15) 0.5110(9) 0.070(6) Uani 1 1 d . . . H3G H 1.1005 0.2594 0.4956 0.084 Uiso 1 1 d R . . C4G C 0.9992(18) 0.3540(15) 0.5465(10) 0.070(7) Uani 1 1 d . . . H4G H 1.0584 0.4018 0.5473 0.083 Uiso 1 1 d R . . C5G C 0.876(2) 0.3791(18) 0.5710(11) 0.089(8) Uani 1 1 d U . . H5G H 0.8604 0.4272 0.5969 0.107 Uiso 1 1 d R . . C6G C 0.788(2) 0.3283(17) 0.5595(11) 0.083(8) Uani 1 1 d . . . H6G H 0.7072 0.3451 0.5760 0.099 Uiso 1 1 d R . . N1H N 0.4204(13) 0.1265(10) 0.5109(6) 0.045(4) Uani 1 1 d . . . H1H H 0.4437 0.1085 0.4769 0.054 Uiso 1 1 d R . . C2H C 0.5047(19) 0.1578(14) 0.5344(9) 0.048(5) Uani 1 1 d . . . O2H O 0.6188(12) 0.1596(9) 0.5030(6) 0.060(4) Uani 1 1 d . . . C3H C 0.4696(18) 0.1939(13) 0.5864(9) 0.053(5) Uani 1 1 d U . . H3H H 0.5294 0.2139 0.6034 0.063 Uiso 1 1 d R . . C4H C 0.347(2) 0.1900(15) 0.6161(10) 0.075(7) Uani 1 1 d . . . H4H H 0.3216 0.2181 0.6503 0.090 Uiso 1 1 d R . . C5H C 0.2583(19) 0.1543(17) 0.5892(11) 0.089(8) Uani 1 1 d . . . H5H H 0.1760 0.1438 0.6075 0.106 Uiso 1 1 d R . . C6H C 0.300(2) 0.1203(15) 0.5378(10) 0.069(6) Uani 1 1 d U . . H6H H 0.2426 0.1050 0.5178 0.083 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0808(16) 0.0643(13) 0.0740(17) 0.0030(11) -0.0147(12) 0.0114(11) I2 0.1162(14) 0.0621(10) 0.0865(13) -0.0100(8) -0.0353(10) 0.0024(8) I3 0.0761(10) 0.0705(9) 0.0677(11) -0.0381(8) -0.0242(8) 0.0142(7) I4 0.0979(12) 0.0786(10) 0.0573(11) -0.0269(8) -0.0104(9) -0.0055(8) I5 0.0865(12) 0.0657(10) 0.1130(16) -0.0017(9) -0.0125(10) 0.0058(8) I6 0.0645(10) 0.0728(10) 0.1024(14) -0.0012(9) 0.0038(9) 0.0032(8) I7 0.0621(11) 0.0878(11) 0.1076(15) -0.0065(10) -0.0077(10) -0.0029(8) I8 0.0753(10) 0.0668(9) 0.0571(10) -0.0067(7) -0.0225(8) -0.0163(7) I9 0.0712(10) 0.0749(10) 0.0622(11) -0.0187(8) -0.0147(8) -0.0024(7) I10 0.0694(10) 0.0842(10) 0.0624(11) -0.0404(8) -0.0185(8) 0.0181(8) I11 0.1006(12) 0.0788(10) 0.0627(11) -0.0326(8) -0.0293(9) 0.0123(8) I12 0.0941(19) 0.1082(19) 0.098(2) -0.0195(15) -0.0075(15) 0.0192(14) I13 0.1297(15) 0.0756(11) 0.1265(17) -0.0058(10) -0.0808(13) -0.0112(9) I14 0.1258(15) 0.0936(12) 0.0611(12) -0.0125(9) -0.0219(10) -0.0435(10) N1A 0.039(7) 0.046(7) 0.046(8) -0.029(6) -0.016(6) -0.004(6) C2A 0.043(9) 0.042(8) 0.057(9) -0.013(7) -0.018(8) 0.001(7) O2A 0.044(9) 0.054(8) 0.069(10) -0.018(7) -0.022(7) -0.002(6) C3A 0.027(12) 0.119(18) 0.060(16) -0.007(13) -0.017(11) -0.018(11) C4A 0.070(10) 0.067(9) 0.050(9) -0.024(7) -0.007(8) -0.003(8) C5A 0.060(16) 0.117(19) 0.033(14) -0.026(13) 0.014(12) 0.018(13) C6A 0.032(13) 0.056(13) 0.077(18) -0.003(12) -0.013(12) -0.002(9) N1B 0.058(12) 0.057(10) 0.047(11) -0.035(8) -0.013(9) -0.007(8) C2B 0.053(9) 0.057(8) 0.042(9) -0.012(7) -0.022(7) 0.005(7) O2B 0.052(9) 0.065(9) 0.079(11) -0.037(8) -0.006(8) 0.005(6) C3B 0.044(9) 0.064(9) 0.069(10) -0.005(8) -0.016(8) -0.012(7) C4B 0.073(10) 0.106(11) 0.090(11) -0.023(9) -0.023(8) -0.014(8) C5B 0.072(17) 0.091(17) 0.11(2) -0.082(15) -0.021(15) -0.003(13) C6B 0.049(14) 0.090(16) 0.049(15) -0.023(12) -0.013(11) -0.001(11) N1C 0.047(11) 0.053(10) 0.043(11) -0.006(8) -0.014(8) -0.005(8) C2C 0.031(12) 0.036(11) 0.049(13) -0.012(9) -0.016(10) 0.007(9) O2C 0.047(8) 0.047(8) 0.062(10) -0.017(7) -0.011(7) 0.001(6) C3C 0.058(14) 0.052(12) 0.062(15) -0.034(11) 0.000(11) -0.035(10) C4C 0.058(15) 0.055(13) 0.077(17) -0.004(12) -0.049(13) -0.012(10) C5C 0.083(19) 0.071(15) 0.09(2) -0.039(14) -0.033(16) -0.009(13) C6C 0.057(14) 0.067(13) 0.034(13) -0.037(11) 0.009(10) 0.004(11) N1D 0.042(10) 0.047(9) 0.038(10) -0.012(7) -0.010(8) 0.001(7) C2D 0.060(15) 0.063(13) 0.041(14) -0.028(11) -0.019(12) -0.002(11) O2D 0.038(8) 0.104(11) 0.042(9) -0.033(8) -0.004(7) 0.007(7) C3D 0.058(9) 0.061(8) 0.061(9) -0.032(7) -0.016(8) 0.000(7) C4D 0.048(15) 0.134(19) 0.047(14) -0.050(13) -0.013(11) -0.003(13) C5D 0.079(10) 0.096(10) 0.089(11) -0.034(8) -0.024(8) 0.003(8) C6D 0.063(9) 0.062(9) 0.056(9) -0.024(7) -0.019(8) -0.015(7) N1E 0.021(10) 0.093(12) 0.046(11) -0.027(9) -0.010(9) 0.009(8) C2E 0.038(13) 0.035(10) 0.057(15) -0.022(10) -0.020(12) 0.007(9) O2E 0.036(8) 0.075(9) 0.043(8) -0.038(7) -0.009(7) 0.001(6) C3E 0.065(15) 0.043(11) 0.061(15) -0.015(10) -0.038(12) 0.000(10) C4E 0.069(10) 0.079(9) 0.051(9) -0.016(8) -0.014(8) 0.005(8) C5E 0.042(13) 0.116(18) 0.063(17) -0.047(14) -0.018(12) -0.015(12) C6E 0.063(17) 0.059(13) 0.09(2) -0.010(13) -0.041(15) -0.020(11) N1F 0.038(10) 0.057(10) 0.043(11) -0.014(8) -0.017(8) -0.002(8) C2F 0.071(17) 0.060(13) 0.034(13) -0.023(10) -0.012(12) -0.007(11) O2F 0.040(8) 0.081(9) 0.063(10) -0.041(8) -0.019(7) -0.001(6) C3F 0.035(12) 0.065(13) 0.048(14) -0.010(11) -0.008(10) -0.006(10) C4F 0.063(17) 0.081(16) 0.073(18) -0.016(13) -0.029(14) -0.035(12) C5F 0.082(18) 0.064(14) 0.061(16) -0.033(12) -0.022(14) 0.006(12) C6F 0.055(9) 0.065(9) 0.048(9) -0.019(8) -0.015(8) -0.006(7) N1G 0.040(11) 0.043(9) 0.043(11) 0.011(8) -0.028(8) -0.015(7) C2G 0.029(12) 0.059(13) 0.036(12) -0.010(10) -0.014(10) -0.013(10) O2G 0.055(9) 0.061(8) 0.072(11) -0.049(8) -0.011(7) -0.005(6) C3G 0.069(16) 0.061(14) 0.091(19) -0.045(13) -0.013(13) -0.014(11) C4G 0.052(15) 0.073(15) 0.11(2) -0.050(14) -0.042(13) 0.001(11) C5G 0.087(11) 0.096(11) 0.095(11) -0.040(8) -0.023(9) 0.009(9) C6G 0.066(17) 0.064(15) 0.13(2) -0.040(15) -0.040(16) 0.021(12) N1H 0.043(10) 0.063(10) 0.038(10) -0.032(8) -0.004(8) -0.017(8) C2H 0.054(15) 0.052(12) 0.041(14) -0.026(10) -0.002(11) -0.003(10) O2H 0.057(9) 0.071(9) 0.057(10) -0.017(7) -0.022(8) 0.002(7) C3H 0.059(9) 0.054(8) 0.052(9) -0.036(7) -0.003(7) -0.003(7) C4H 0.080(18) 0.067(14) 0.072(18) -0.041(12) 0.021(14) -0.002(12) C5H 0.045(15) 0.112(19) 0.11(2) -0.069(17) 0.023(15) -0.038(13) C6H 0.057(10) 0.079(9) 0.071(10) -0.018(8) -0.013(8) 0.005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9454(18) . ? I1 I2 2.9454(18) 2 ? I2 I3 3.173(2) . ? I3 I4 2.778(2) . ? I5 I6 2.793(3) . ? I6 I7 3.328(3) . ? I7 I8 2.909(2) . ? I8 I9 2.933(2) . ? I9 I10 3.307(2) . ? I10 I11 2.759(2) . ? I12 I13 3.315(2) . ? I13 I14 2.774(3) . ? N1A C2A 1.31(2) . ? N1A C6A 1.346(19) . ? C2A O2A 1.303(19) . ? C2A C3A 1.41(3) . ? C3A C4A 1.32(2) . ? C4A C5A 1.42(3) . ? C5A C6A 1.34(2) . ? N1B C2B 1.31(2) . ? N1B C6B 1.33(2) . ? C2B O2B 1.28(2) . ? C2B C3B 1.43(2) . ? C3B C4B 1.30(3) . ? C4B C5B 1.46(3) . ? C5B C6B 1.36(2) . ? N1C C6C 1.306(19) . ? N1C C2C 1.363(19) . ? C2C O2C 1.288(18) . ? C2C C3C 1.43(2) . ? C3C C4C 1.34(2) . ? C4C C5C 1.44(3) . ? C5C C6C 1.37(2) . ? N1D C6D 1.30(2) . ? N1D C2D 1.39(2) . ? C2D O2D 1.22(2) . ? C2D C3D 1.43(2) . ? C3D C4D 1.34(2) . ? C4D C5D 1.40(3) . ? C5D C6D 1.42(3) . ? N1E C2E 1.29(2) . ? N1E C6E 1.35(2) . ? C2E O2E 1.267(19) . ? C2E C3E 1.46(2) . ? C3E C4E 1.34(2) . ? C4E C5E 1.35(2) . ? C5E C6E 1.37(3) . ? N1F C6F 1.34(2) . ? N1F C2F 1.35(2) . ? C2F O2F 1.269(19) . ? C2F C3F 1.42(2) . ? C3F C4F 1.37(2) . ? C4F C5F 1.41(2) . ? C5F C6F 1.30(2) . ? N1G C2G 1.32(2) . ? N1G C6G 1.33(2) . ? C2G O2G 1.263(19) . ? C2G C3G 1.41(2) . ? C3G C4G 1.36(2) . ? C4G C5G 1.41(3) . ? C5G C6G 1.32(3) . ? N1H C2H 1.32(2) . ? N1H C6H 1.36(2) . ? C2H O2H 1.323(19) . ? C2H C3H 1.36(2) . ? C3H C4H 1.39(2) . ? C4H C5H 1.44(3) . ? C5H C6H 1.34(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 I2 I1 I2 180.00(4) . 2 ? I1 I2 I3 92.14(5) . . ? I4 I3 I2 174.93(7) . . ? I5 I6 I7 174.99(7) . . ? I8 I7 I6 88.86(6) . . ? I7 I8 I9 178.42(7) . . ? I8 I9 I10 85.17(5) . . ? I11 I10 I9 179.91(7) . . ? I14 I13 I12 167.52(7) . . ? C2A N1A C6A 125.2(18) . . ? O2A C2A N1A 119.8(19) . . ? O2A C2A C3A 123.5(18) . . ? N1A C2A C3A 116.6(18) . . ? C4A C3A C2A 119(2) . . ? C3A C4A C5A 123(2) . . ? C6A C5A C4A 116(2) . . ? C5A C6A N1A 120.1(19) . . ? C2B N1B C6B 125.7(17) . . ? O2B C2B N1B 120.7(18) . . ? O2B C2B C3B 125(2) . . ? N1B C2B C3B 114(2) . . ? C4B C3B C2B 123(2) . . ? C3B C4B C5B 121(2) . . ? C6B C5B C4B 114(2) . . ? N1B C6B C5B 121.9(19) . . ? C6C N1C C2C 122.9(16) . . ? O2C C2C N1C 117.4(15) . . ? O2C C2C C3C 123.2(16) . . ? N1C C2C C3C 119.0(17) . . ? C4C C3C C2C 115.5(18) . . ? C3C C4C C5C 125.1(18) . . ? C6C C5C C4C 113.0(19) . . ? N1C C6C C5C 122.8(19) . . ? C6D N1D C2D 123.2(17) . . ? O2D C2D N1D 118.5(18) . . ? O2D C2D C3D 126.3(18) . . ? N1D C2D C3D 115.2(18) . . ? C4D C3D C2D 121.0(19) . . ? C3D C4D C5D 123(2) . . ? C4D C5D C6D 114(2) . . ? N1D C6D C5D 122.9(19) . . ? C2E N1E C6E 124.2(19) . . ? O2E C2E N1E 120.6(19) . . ? O2E C2E C3E 122.0(17) . . ? N1E C2E C3E 116.8(18) . . ? C4E C3E C2E 114.8(18) . . ? C3E C4E C5E 129(2) . . ? C4E C5E C6E 112(2) . . ? N1E C6E C5E 122.7(18) . . ? C6F N1F C2F 122.3(16) . . ? O2F C2F N1F 118.4(18) . . ? O2F C2F C3F 124(2) . . ? N1F C2F C3F 117.2(18) . . ? C4F C3F C2F 118.3(18) . . ? C3F C4F C5F 121.3(18) . . ? C6F C5F C4F 117(2) . . ? C5F C6F N1F 123(2) . . ? C2G N1G C6G 125.1(17) . . ? O2G C2G N1G 118.7(16) . . ? O2G C2G C3G 126.9(18) . . ? N1G C2G C3G 114.3(18) . . ? C4G C3G C2G 122(2) . . ? C3G C4G C5G 117.6(19) . . ? C6G C5G C4G 119(2) . . ? C5G C6G N1G 121(2) . . ? C2H N1H C6H 123.6(18) . . ? N1H C2H O2H 116.7(17) . . ? N1H C2H C3H 119.2(18) . . ? O2H C2H C3H 123.9(19) . . ? C2H C3H C4H 120.0(19) . . ? C3H C4H C5H 119(2) . . ? C6H C5H C4H 118(2) . . ? C5H C6H N1H 120(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 I1 I2 I3 133(100) 2 . . . ? I1 I2 I3 I4 34.4(8) . . . . ? I5 I6 I7 I8 -126.4(7) . . . . ? I6 I7 I8 I9 22(2) . . . . ? I7 I8 I9 I10 72(2) . . . . ? I8 I9 I10 I11 -66(75) . . . . ? C6A N1A C2A O2A -173.7(14) . . . . ? C6A N1A C2A C3A 2(3) . . . . ? O2A C2A C3A C4A 173.1(16) . . . . ? N1A C2A C3A C4A -2(3) . . . . ? C2A C3A C4A C5A 3(3) . . . . ? C3A C4A C5A C6A -4(3) . . . . ? C4A C5A C6A N1A 3(3) . . . . ? C2A N1A C6A C5A -2(3) . . . . ? C6B N1B C2B O2B -174.4(17) . . . . ? C6B N1B C2B C3B 0(3) . . . . ? O2B C2B C3B C4B 177(2) . . . . ? N1B C2B C3B C4B 2(3) . . . . ? C2B C3B C4B C5B 0(3) . . . . ? C3B C4B C5B C6B -4(3) . . . . ? C2B N1B C6B C5B -5(3) . . . . ? C4B C5B C6B N1B 7(3) . . . . ? C6C N1C C2C O2C -179.0(15) . . . . ? C6C N1C C2C C3C -6(2) . . . . ? O2C C2C C3C C4C 178.7(17) . . . . ? N1C C2C C3C C4C 6(2) . . . . ? C2C C3C C4C C5C -11(3) . . . . ? C3C C4C C5C C6C 14(3) . . . . ? C2C N1C C6C C5C 10(3) . . . . ? C4C C5C C6C N1C -13(3) . . . . ? C6D N1D C2D O2D 179.6(16) . . . . ? C6D N1D C2D C3D 2(2) . . . . ? O2D C2D C3D C4D -177.8(18) . . . . ? N1D C2D C3D C4D -1(3) . . . . ? C2D C3D C4D C5D -4(3) . . . . ? C3D C4D C5D C6D 7(3) . . . . ? C2D N1D C6D C5D 1(3) . . . . ? C4D C5D C6D N1D -6(3) . . . . ? C6E N1E C2E O2E 177.2(15) . . . . ? C6E N1E C2E C3E 6(3) . . . . ? O2E C2E C3E C4E -175.1(15) . . . . ? N1E C2E C3E C4E -4(2) . . . . ? C2E C3E C4E C5E 4(3) . . . . ? C3E C4E C5E C6E -5(3) . . . . ? C2E N1E C6E C5E -7(3) . . . . ? C4E C5E C6E N1E 6(3) . . . . ? C6F N1F C2F O2F 179.8(16) . . . . ? C6F N1F C2F C3F -1(3) . . . . ? O2F C2F C3F C4F -177.0(18) . . . . ? N1F C2F C3F C4F 3(3) . . . . ? C2F C3F C4F C5F -5(3) . . . . ? C3F C4F C5F C6F 4(3) . . . . ? C4F C5F C6F N1F -1(3) . . . . ? C2F N1F C6F C5F 0(3) . . . . ? C6G N1G C2G O2G -175.2(17) . . . . ? C6G N1G C2G C3G 7(3) . . . . ? O2G C2G C3G C4G -177.2(19) . . . . ? N1G C2G C3G C4G 0(3) . . . . ? C2G C3G C4G C5G -4(3) . . . . ? C3G C4G C5G C6G 1(3) . . . . ? C4G C5G C6G N1G 6(4) . . . . ? C2G N1G C6G C5G -10(3) . . . . ? C6H N1H C2H O2H 179.9(15) . . . . ? C6H N1H C2H C3H -5(3) . . . . ? N1H C2H C3H C4H 5(3) . . . . ? O2H C2H C3H C4H 179.4(16) . . . . ? C2H C3H C4H C5H -4(3) . . . . ? C3H C4H C5H C6H 4(3) . . . . ? C4H C5H C6H N1H -4(3) . . . . ? C2H N1H C6H C5H 5(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 N1A H1A O2D 0.86 2.00 2.854(18) 170.8 1_654 C3A H3A I14 0.93 3.42 4.08(2) 130.0 . C4A H4A I13 0.93 3.56 4.46(2) 161.9 . C5A H5A I6 0.93 3.31 4.23(2) 171.1 . C6A H6BA I8 0.93 3.31 4.131(19) 148.3 . C6A H6BA I9 0.93 3.37 4.004(19) 127.3 . N1B H1B O2A 0.86 1.92 2.769(18) 171.9 1_455 O2B H2B O2C 0.82 1.65 2.437(15) 159.1 1_554 C4B H4B I10 0.93 3.49 4.33(2) 151.0 1_565 C4B H4B I11 0.93 3.41 3.90(3) 115.3 1_565 C5B H5B I4 0.93 3.58 4.11(2) 119.6 1_565 C6B H6B I4 0.93 3.19 3.95(2) 140.2 1_565 N1C H1C O2D 0.86 1.89 2.739(19) 169.7 1_655 O2C H2C O2B 0.82 1.64 2.437(16) 165.3 1_556 C4C H4C I9 0.93 3.28 4.084(19) 145.5 2_656 C5C H5C I8 0.93 3.41 4.32(2) 166.2 2_656 C6C H6C I1 0.93 3.49 4.092(19) 124.7 1_656 C6C H6C I2 0.93 3.46 4.132(18) 131.2 2_656 C6C H6C I3 0.93 3.32 4.173(17) 153.3 2_656 N1D H1D O2A 0.86 1.89 2.745(19) 170.5 1_456 C3D H3D I3 0.93 3.29 3.976(19) 132.0 2_556 C4D H4D I10 0.93 3.36 3.98(2) 126.3 2_656 C4D H4D I4 0.93 3.37 4.16(2) 144.6 2_556 C5D H5D I10 0.93 3.55 4.14(2) 123.8 2_656 C6D H6D O2B 0.93 2.52 3.30(2) 142.0 1_556 N1E H1E O2H 0.86 1.95 2.81(2) 177.6 . C3E H3E I8 0.93 3.55 4.241(18) 133.4 . C4E H4E I9 0.93 3.37 4.16(2) 143.5 . C5E H5E I7 0.93 3.11 4.04(2) 173.5 1_655 C6E H6E O2G 0.93 2.67 3.52(2) 152.4 . C6E H6E I14 0.93 3.46 4.012(18) 120.2 . N1F H1F O2E 0.86 1.86 2.712(18) 172.2 . O2F H2F O2G 0.82 1.78 2.449(16) 137.5 1_455 C4F H4F I3 0.93 3.37 4.06(2) 133.1 . C4F H4F I4 0.93 3.22 4.03(2) 147.0 . C6F H6F I10 0.93 3.25 4.06(2) 146.3 . N1G H1G O2H 0.86 1.93 2.764(18) 162.4 . O2G H2G O2F 0.82 1.63 2.449(16) 174.6 1_655 C4G H4G I13 0.93 3.26 4.152(19) 161.5 2_766 C5G H5G I14 0.93 3.34 4.10(3) 140.8 2_766 C6G H6G I11 0.93 3.45 4.25(2) 145.4 2_656 N1H H1H O2E 0.86 1.96 2.817(18) 172.1 . C3H H3H I11 0.93 3.32 3.967(18) 128.2 2_656 C4H H4H I4 0.93 3.31 4.024(19) 135.5 2_556 C4H H4H I11 0.93 3.43 4.03(2) 125.2 2_656 C4H H4H I10 0.93 3.54 4.23(2) 133.4 2_656 C6H H6H O2F 0.93 2.44 3.33(3) 159.6 . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.874 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.181