# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Edwin Weber' _publ_contact_author_email EDWIN.WEBER@CHEMIE.TU-FREIBERG.DE _publ_section_title ; Rigid rod and tetrahedral hybrid compounds featuring nucleobase and nucleoside end-capped structures ; loop_ _publ_author_name 'Edwin Weber' 'Frank Eibmann' 'Diana Schindler' # Attachment 'schind_1.cif' data_schind_1 _database_code_depnum_ccdc_archive 'CCDC 722856' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Bis(pyrimidine-2,4-dione-5-yl)butadiyne ; _chemical_name_common 1,4-Bis(pyrimidine-2,4-dione-5-yl)butadiyne _chemical_melting_point ? _chemical_formula_moiety 'C12 H6 N4 O4, 2(C2 H6 O S)' _chemical_formula_sum 'C16 H18 N4 O6 S2' _chemical_formula_weight 426.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 17.635(3) _cell_length_b 11.989(3) _cell_length_c 9.298(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.961(13) _cell_angle_gamma 90.00 _cell_volume 1915.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 3278 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9566 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 Kappa APEXII CCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31536 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3370 _reflns_number_gt 2463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-NT (Bruker, 2004)' _computing_data_reduction 'SAINT-NT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0658P)^2^+0.1786P] 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 3370 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 -0.01845(11) 0.54124(16) 0.7920(2) 0.0278(5) Uani 1 1 d . . . O2 O 0.16428(11) 0.57666(16) 0.5199(2) 0.0271(5) Uani 1 1 d . . . O3 O 0.53646(12) 1.25377(16) 0.2488(2) 0.0355(6) Uani 1 1 d . . . O4 O 0.33854(11) 1.21544(16) 0.4853(2) 0.0279(5) Uani 1 1 d . . . N1 N 0.02909(13) 0.71595(19) 0.7641(2) 0.0191(5) Uani 1 1 d . . . N2 N 0.07506(12) 0.5610(2) 0.6608(3) 0.0206(5) Uani 1 1 d . . . N3 N 0.49068(13) 1.07884(19) 0.2734(3) 0.0220(6) Uani 1 1 d . . . N4 N 0.43830(13) 1.2315(2) 0.3685(3) 0.0247(6) Uani 1 1 d . . . C1 C 0.07736(14) 0.7836(2) 0.7080(3) 0.0202(6) Uani 1 1 d . . . H1 H 0.0773 0.8615 0.7265 0.024 Uiso 1 1 calc R . . C2 C 0.02537(16) 0.6018(2) 0.7423(3) 0.0212(6) Uani 1 1 d . . . C3 C 0.12450(15) 0.6234(2) 0.5953(3) 0.0189(6) Uani 1 1 d . . . C4 C 0.12546(15) 0.7421(2) 0.6262(3) 0.0189(6) Uani 1 1 d . . . C5 C 0.17648(15) 0.8109(2) 0.5650(3) 0.0207(6) Uani 1 1 d . . . C6 C 0.22328(16) 0.8638(2) 0.5157(3) 0.0207(6) Uani 1 1 d . . . C7 C 0.27871(16) 0.9256(2) 0.4678(3) 0.0225(7) Uani 1 1 d . . . C8 C 0.32930(16) 0.9799(2) 0.4344(3) 0.0203(6) Uani 1 1 d . . . C9 C 0.38572(15) 1.0498(2) 0.3914(3) 0.0210(6) Uani 1 1 d . . . C10 C 0.38411(15) 1.1694(2) 0.4215(3) 0.0211(6) Uani 1 1 d . . . C11 C 0.49150(15) 1.1927(2) 0.2935(3) 0.0243(7) Uani 1 1 d . . . C12 C 0.43950(15) 1.0106(2) 0.3198(3) 0.0211(6) Uani 1 1 d . . . H12 H 0.4414 0.9328 0.3016 0.025 Uiso 1 1 calc R . . H1N H -0.0028(16) 0.741(2) 0.819(3) 0.028(8) Uiso 1 1 d . . . H2N H 0.0697(16) 0.484(3) 0.631(3) 0.035(9) Uiso 1 1 d . . . H3N H 0.5268(18) 1.044(3) 0.218(3) 0.043(9) Uiso 1 1 d . . . H4N H 0.4373(17) 1.308(3) 0.383(3) 0.038(9) Uiso 1 1 d . . . S1 S 0.13209(4) 0.20356(6) 0.00994(7) 0.0187(2) Uani 1 1 d . . . O5 O 0.06368(10) 0.16956(15) 0.0753(2) 0.0200(4) Uani 1 1 d . . . C13 C 0.21593(15) 0.1757(2) 0.1522(3) 0.0234(7) Uani 1 1 d . . . H13A H 0.2092 0.2089 0.2449 0.035 Uiso 1 1 calc R . . H13B H 0.2619 0.2080 0.1254 0.035 Uiso 1 1 calc R . . H13C H 0.2228 0.0949 0.1647 0.035 Uiso 1 1 calc R . . C14 C 0.13405(16) 0.3526(2) 0.0138(3) 0.0237(7) Uani 1 1 d . . . H14A H 0.0899 0.3818 -0.0601 0.035 Uiso 1 1 calc R . . H14B H 0.1828 0.3791 -0.0083 0.035 Uiso 1 1 calc R . . H14C H 0.1305 0.3788 0.1120 0.035 Uiso 1 1 calc R . . S2 S 0.64836(4) -0.00038(6) 0.04569(8) 0.0260(2) Uani 1 1 d . . . O6 O 0.58041(11) -0.03390(17) 0.1116(2) 0.0311(5) Uani 1 1 d . . . C15 C 0.73191(16) -0.0462(2) 0.1761(3) 0.0259(7) Uani 1 1 d . . . H15A H 0.7287 -0.0215 0.2750 0.039 Uiso 1 1 calc R . . H15B H 0.7786 -0.0147 0.1513 0.039 Uiso 1 1 calc R . . H15C H 0.7346 -0.1279 0.1741 0.039 Uiso 1 1 calc R . . C16 C 0.66076(19) 0.1459(3) 0.0747(4) 0.0414(9) Uani 1 1 d . . . H16A H 0.6185 0.1857 0.0079 0.062 Uiso 1 1 calc R . . H16B H 0.7108 0.1688 0.0550 0.062 Uiso 1 1 calc R . . H16C H 0.6598 0.1637 0.1771 0.062 Uiso 1 1 calc R . . Cg1 C 0.1999 0.8374 0.5403 0.010 Uiso 0.00 1 d P . . Cg2 C 0.3040 0.9527 0.4511 0.010 Uiso 0.00 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 0.0303(11) 0.0192(11) 0.0405(12) 0.0006(9) 0.0223(10) -0.0033(9) O2 0.0317(11) 0.0212(11) 0.0347(12) -0.0011(9) 0.0211(10) 0.0012(9) O3 0.0340(12) 0.0215(12) 0.0595(15) 0.0012(10) 0.0285(11) -0.0058(10) O4 0.0315(11) 0.0225(11) 0.0352(12) -0.0007(9) 0.0189(10) 0.0033(9) N1 0.0213(12) 0.0170(13) 0.0231(13) -0.0012(10) 0.0133(11) 0.0010(10) N2 0.0223(13) 0.0143(13) 0.0265(13) 0.0018(11) 0.0083(11) 0.0009(10) N3 0.0212(13) 0.0186(14) 0.0305(14) 0.0004(11) 0.0148(11) 0.0002(10) N4 0.0261(13) 0.0156(14) 0.0352(15) 0.0004(11) 0.0129(11) -0.0012(11) C1 0.0213(14) 0.0172(15) 0.0228(15) -0.0006(12) 0.0062(12) 0.0001(12) C2 0.0225(15) 0.0178(15) 0.0250(16) 0.0018(13) 0.0090(13) 0.0024(12) C3 0.0210(15) 0.0203(16) 0.0170(15) 0.0022(12) 0.0074(12) -0.0008(12) C4 0.0209(14) 0.0172(15) 0.0192(14) -0.0012(12) 0.0058(12) -0.0033(11) C5 0.0227(15) 0.0195(15) 0.0214(15) -0.0016(12) 0.0084(12) 0.0022(12) C6 0.0235(15) 0.0169(15) 0.0228(15) -0.0018(12) 0.0077(13) 0.0011(12) C7 0.0270(16) 0.0181(16) 0.0238(16) -0.0029(12) 0.0083(13) 0.0040(13) C8 0.0226(15) 0.0174(15) 0.0247(15) -0.0019(12) 0.0130(13) -0.0016(12) C9 0.0208(15) 0.0200(15) 0.0228(15) 0.0025(12) 0.0066(12) 0.0015(12) C10 0.0196(15) 0.0222(16) 0.0233(15) -0.0030(12) 0.0088(13) -0.0011(12) C11 0.0204(15) 0.0194(16) 0.0351(17) 0.0004(13) 0.0107(13) -0.0011(12) C12 0.0203(15) 0.0162(15) 0.0273(16) 0.0025(12) 0.0066(12) -0.0014(12) S1 0.0194(4) 0.0167(4) 0.0224(4) -0.0004(3) 0.0098(3) -0.0009(3) O5 0.0190(10) 0.0159(10) 0.0286(11) 0.0000(8) 0.0129(8) 0.0000(8) C13 0.0228(15) 0.0230(16) 0.0262(16) -0.0017(13) 0.0095(13) -0.0025(12) C14 0.0226(15) 0.0183(16) 0.0323(17) 0.0024(13) 0.0110(13) -0.0005(12) S2 0.0266(4) 0.0256(4) 0.0278(4) 0.0061(3) 0.0107(3) 0.0055(3) O6 0.0251(11) 0.0236(12) 0.0479(13) 0.0007(10) 0.0151(10) 0.0047(9) C15 0.0275(16) 0.0234(17) 0.0280(16) 0.0040(13) 0.0089(13) 0.0020(13) C16 0.0375(19) 0.0242(18) 0.070(2) 0.0135(17) 0.0267(18) 0.0066(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.224(3) . ? O2 C3 1.232(3) . ? O3 C11 1.219(3) . ? O4 C10 1.231(3) . ? N1 C1 1.362(3) . ? N1 C2 1.383(4) . ? N1 H1N 0.89(3) . ? N2 C2 1.371(3) . ? N2 C3 1.389(3) . ? N2 H2N 0.96(3) . ? N3 C12 1.358(3) . ? N3 C11 1.377(4) . ? N3 H3N 1.00(3) . ? N4 C11 1.370(4) . ? N4 C10 1.386(3) . ? N4 H4N 0.93(3) . ? C1 C4 1.354(4) . ? C1 H1 0.9500 . ? C3 C4 1.451(4) . ? C4 C5 1.429(4) . ? C4 Cg1 2.033(3) . ? C5 Cg1 0.605(3) . ? C5 C6 1.210(4) . ? C6 Cg1 0.605(3) . ? C6 C7 1.377(4) . ? C6 Cg2 1.977(3) . ? C7 Cg2 0.600(3) . ? C7 C8 1.201(4) . ? C7 Cg1 1.981(3) . ? C8 Cg2 0.600(3) . ? C8 C9 1.425(4) . ? C9 C12 1.358(4) . ? C9 C10 1.463(4) . ? C9 Cg2 2.024(3) . ? C12 H12 0.9500 . ? S1 O5 1.5230(18) . ? S1 C13 1.780(3) . ? S1 C14 1.788(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? S2 O6 1.517(2) . ? S2 C15 1.772(3) . ? S2 C16 1.780(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.1(2) . . ? C1 N1 H1N 123.4(19) . . ? C2 N1 H1N 113.5(19) . . ? C2 N2 C3 126.3(2) . . ? C2 N2 H2N 118.0(17) . . ? C3 N2 H2N 114.8(17) . . ? C12 N3 C11 122.8(2) . . ? C12 N3 H3N 117.5(19) . . ? C11 N3 H3N 119.6(19) . . ? C11 N4 C10 127.2(3) . . ? C11 N4 H4N 116.6(19) . . ? C10 N4 H4N 116.3(19) . . ? C4 C1 N1 121.4(3) . . ? C4 C1 H1 119.3 . . ? N1 C1 H1 119.3 . . ? O1 C2 N2 122.2(3) . . ? O1 C2 N1 123.0(2) . . ? N2 C2 N1 114.8(2) . . ? O2 C3 N2 119.9(2) . . ? O2 C3 C4 125.2(2) . . ? N2 C3 C4 114.9(2) . . ? C1 C4 C5 122.7(3) . . ? C1 C4 C3 119.4(2) . . ? C5 C4 C3 117.9(2) . . ? C1 C4 Cg1 123.7(2) . . ? C5 C4 Cg1 1.26(11) . . ? C3 C4 Cg1 116.94(18) . . ? Cg1 C5 C6 0.0(3) . . ? Cg1 C5 C4 175.8(4) . . ? C6 C5 C4 175.8(3) . . ? Cg1 C6 C5 0.0(2) . . ? Cg1 C6 C7 176.7(4) . . ? C5 C6 C7 176.7(3) . . ? Cg1 C6 Cg2 175.6(3) . . ? C5 C6 Cg2 175.6(2) . . ? C7 C6 Cg2 1.14(12) . . ? Cg2 C7 C8 0.0(2) . . ? Cg2 C7 C6 176.2(4) . . ? C8 C7 C6 176.2(3) . . ? Cg2 C7 Cg1 175.2(3) . . ? C8 C7 Cg1 175.2(2) . . ? C6 C7 Cg1 1.01(12) . . ? Cg2 C8 C7 0.0(2) . . ? Cg2 C8 C9 176.3(4) . . ? C7 C8 C9 176.3(3) . . ? C12 C9 C8 122.9(3) . . ? C12 C9 C10 118.6(2) . . ? C8 C9 C10 118.6(2) . . ? C12 C9 Cg2 123.6(2) . . ? C8 C9 Cg2 1.09(12) . . ? C10 C9 Cg2 117.73(19) . . ? O4 C10 N4 120.5(3) . . ? O4 C10 C9 125.1(3) . . ? N4 C10 C9 114.4(2) . . ? O3 C11 N4 122.8(3) . . ? O3 C11 N3 122.5(3) . . ? N4 C11 N3 114.7(2) . . ? N3 C12 C9 122.3(3) . . ? N3 C12 H12 118.9 . . ? C9 C12 H12 118.9 . . ? O5 S1 C13 104.69(12) . . ? O5 S1 C14 105.84(11) . . ? C13 S1 C14 99.39(13) . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O6 S2 C15 104.61(12) . . ? O6 S2 C16 106.32(13) . . ? C15 S2 C16 98.45(15) . . ? S2 C15 H15A 109.5 . . ? S2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S2 C16 H16A 109.5 . . ? S2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 Cg1 C5 180.0(5) . . ? C6 Cg1 C7 2.3(3) . . ? C5 Cg1 C7 177.7(3) . . ? C6 Cg1 C4 177.0(3) . . ? C5 Cg1 C4 3.0(3) . . ? C7 Cg1 C4 175.81(11) . . ? C7 Cg2 C8 180.0(5) . . ? C7 Cg2 C6 2.6(3) . . ? C8 Cg2 C6 177.4(3) . . ? C7 Cg2 C9 177.4(3) . . ? C8 Cg2 C9 2.6(3) . . ? C6 Cg2 C9 177.23(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 C4 -0.1(4) . . . . ? C3 N2 C2 O1 177.3(3) . . . . ? C3 N2 C2 N1 -3.0(4) . . . . ? C1 N1 C2 O1 -179.5(3) . . . . ? C1 N1 C2 N2 0.8(4) . . . . ? C2 N2 C3 O2 -177.3(2) . . . . ? C2 N2 C3 C4 4.0(4) . . . . ? N1 C1 C4 C5 179.6(2) . . . . ? N1 C1 C4 C3 1.2(4) . . . . ? N1 C1 C4 Cg1 -179.37(18) . . . . ? O2 C3 C4 C1 178.4(3) . . . . ? N2 C3 C4 C1 -2.9(4) . . . . ? O2 C3 C4 C5 -0.1(4) . . . . ? N2 C3 C4 C5 178.6(2) . . . . ? O2 C3 C4 Cg1 -1.0(4) . . . . ? N2 C3 C4 Cg1 177.61(17) . . . . ? C1 C4 C5 Cg1 139(5) . . . . ? C3 C4 C5 Cg1 -42(5) . . . . ? C1 C4 C5 C6 139(4) . . . . ? C3 C4 C5 C6 -42(4) . . . . ? Cg1 C4 C5 C6 0(2) . . . . ? C4 C5 C6 Cg1 1(100) . . . . ? Cg1 C5 C6 C7 -76(100) . . . . ? C4 C5 C6 C7 -75(7) . . . . ? Cg1 C5 C6 Cg2 -74(100) . . . . ? C4 C5 C6 Cg2 -73(5) . . . . ? Cg1 C6 C7 Cg2 7(11) . . . . ? C5 C6 C7 Cg2 7(10) . . . . ? Cg1 C6 C7 C8 7(10) . . . . ? C5 C6 C7 C8 7(9) . . . . ? Cg2 C6 C7 C8 0(3) . . . . ? C5 C6 C7 Cg1 0(3) . . . . ? Cg2 C6 C7 Cg1 -7(11) . . . . ? C6 C7 C8 Cg2 -59(100) . . . . ? Cg1 C7 C8 Cg2 -58(100) . . . . ? Cg2 C7 C8 C9 -56(100) . . . . ? C6 C7 C8 C9 -116(5) . . . . ? Cg1 C7 C8 C9 -114(5) . . . . ? Cg2 C8 C9 C12 -137(6) . . . . ? C7 C8 C9 C12 -137(4) . . . . ? Cg2 C8 C9 C10 41(6) . . . . ? C7 C8 C9 C10 41(5) . . . . ? C7 C8 C9 Cg2 0(3) . . . . ? C11 N4 C10 O4 -178.8(3) . . . . ? C11 N4 C10 C9 -0.2(4) . . . . ? C12 C9 C10 O4 -179.9(3) . . . . ? C8 C9 C10 O4 1.9(4) . . . . ? Cg2 C9 C10 O4 2.7(4) . . . . ? C12 C9 C10 N4 1.6(4) . . . . ? C8 C9 C10 N4 -176.6(2) . . . . ? Cg2 C9 C10 N4 -175.75(18) . . . . ? C10 N4 C11 O3 178.9(3) . . . . ? C10 N4 C11 N3 -1.6(4) . . . . ? C12 N3 C11 O3 -178.4(3) . . . . ? C12 N3 C11 N4 2.1(4) . . . . ? C11 N3 C12 C9 -0.8(4) . . . . ? C8 C9 C12 N3 176.9(2) . . . . ? C10 C9 C12 N3 -1.1(4) . . . . ? Cg2 C9 C12 N3 176.01(19) . . . . ? C7 C6 Cg1 C5 104(100) . . . . ? Cg2 C6 Cg1 C5 106(100) . . . . ? C5 C6 Cg1 C7 -104(100) . . . . ? Cg2 C6 Cg1 C7 2(3) . . . . ? C5 C6 Cg1 C4 -179(100) . . . . ? C7 C6 Cg1 C4 -75(9) . . . . ? Cg2 C6 Cg1 C4 -73(7) . . . . ? C4 C5 Cg1 C6 -179(100) . . . . ? C6 C5 Cg1 C7 104(100) . . . . ? C4 C5 Cg1 C7 -75(9) . . . . ? C6 C5 Cg1 C4 179(100) . . . . ? Cg2 C7 Cg1 C6 -174(9) . . . . ? C8 C7 Cg1 C6 -174(8) . . . . ? Cg2 C7 Cg1 C5 6(9) . . . . ? C8 C7 Cg1 C5 6(8) . . . . ? C6 C7 Cg1 C5 -180(100) . . . . ? Cg2 C7 Cg1 C4 -38(5) . . . . ? C8 C7 Cg1 C4 -38(4) . . . . ? C6 C7 Cg1 C4 137(7) . . . . ? C1 C4 Cg1 C6 139(5) . . . . ? C5 C4 Cg1 C6 180(100) . . . . ? C3 C4 Cg1 C6 -42(5) . . . . ? C1 C4 Cg1 C5 -41(5) . . . . ? C3 C4 Cg1 C5 138(5) . . . . ? C1 C4 Cg1 C7 106.7(15) . . . . ? C5 C4 Cg1 C7 148(5) . . . . ? C3 C4 Cg1 C7 -73.9(15) . . . . ? C6 C7 Cg2 C8 121(100) . . . . ? Cg1 C7 Cg2 C8 122(100) . . . . ? C8 C7 Cg2 C6 -121(100) . . . . ? Cg1 C7 Cg2 C6 2(2) . . . . ? C8 C7 Cg2 C9 124(100) . . . . ? C6 C7 Cg2 C9 -116(7) . . . . ? Cg1 C7 Cg2 C9 -114(6) . . . . ? C9 C8 Cg2 C7 124(100) . . . . ? C7 C8 Cg2 C6 121(100) . . . . ? C9 C8 Cg2 C6 -116(7) . . . . ? C7 C8 Cg2 C9 -124(100) . . . . ? Cg1 C6 Cg2 C7 -175(8) . . . . ? C5 C6 Cg2 C7 -175(7) . . . . ? Cg1 C6 Cg2 C8 5(8) . . . . ? C5 C6 Cg2 C8 5(7) . . . . ? C7 C6 Cg2 C8 -180(100) . . . . ? Cg1 C6 Cg2 C9 -52(6) . . . . ? C5 C6 Cg2 C9 -52(4) . . . . ? C7 C6 Cg2 C9 123(6) . . . . ? C12 C9 Cg2 C7 -136(6) . . . . ? C8 C9 Cg2 C7 -180(100) . . . . ? C10 C9 Cg2 C7 41(6) . . . . ? C12 C9 Cg2 C8 44(6) . . . . ? C10 C9 Cg2 C8 -139(6) . . . . ? C12 C9 Cg2 C6 165(2) . . . . ? C8 C9 Cg2 C6 121(6) . . . . ? C10 C9 Cg2 C6 -18(2) . . . . ? 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 N1 H1N O5 0.89(3) 1.93(3) 2.808(3) 166(3) 3_566 N2 H2N O5 0.96(3) 1.91(3) 2.871(3) 177(3) 4_566 N3 H3N O6 1.00(3) 1.78(3) 2.768(3) 171(3) 1_565 N4 H4N O6 0.93(3) 1.92(3) 2.843(3) 171(3) 2_665 C1 H1 O1 0.95 2.38 3.259(3) 153.5 2_556 C15 H15B O2 0.98 2.34 3.216(3) 148.7 2_645 C12 H12 O3 0.95 2.25 3.192(3) 171.3 2_645 C13 H13B O4 0.98 2.27 3.208(3) 159.9 4_575 C16 H16A O3 0.98 2.62 3.529(4) 154.5 4_575 C15 H15A Cg2 0.98 2.86 3.829(3) 171.9 3_666 C16 H16B Cg1 0.98 2.82 3.692(3) 148.0 2_645 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.565 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.071