# Electronic Supplementary Material (ESI) for Medical Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1476 loop_ _publ_author_name 'Medda, Federico' 'Joseph, Thomas' 'Pirrie, Lisa' 'Higgins, Maureen' 'Slawin, Alexandra' 'Lain, Sonia' 'Verma, Chandra' 'Westwood, Nick' _publ_contact_author_name 'Westwood, Nick' _publ_contact_author_email njw3@st-andrews.ac.uk _publ_section_title ; N1-benzyl Substituted Cambinol Analogues as Isozyme Selective Inhibitors of the Sirtuin Family of Protein Deacetylases ; # Attachment '4iv.cif' data_4iv _database_code_depnum_ccdc_archive 'CCDC 809750' #TrackingRef '4iv.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 N2 O2 S' _chemical_formula_sum 'C29 H24 N2 O2 S' _chemical_formula_weight 464.56 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.002(2) _cell_length_b 10.640(3) _cell_length_c 12.1261(18) _cell_angle_alpha 78.20(3) _cell_angle_beta 67.70(2) _cell_angle_gamma 87.07(3) _cell_volume 1168.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4141 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.8 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.792 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7503 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4122 _reflns_number_gt 3376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The NH hydrogen atom was located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.0612P)^2^+0.1497P] 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 4122 _refine_ls_number_parameters 312 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 N1 N 0.69611(15) 0.25548(12) 0.17883(11) 0.0184(3) Uani 1 1 d . . . C2 C 0.76383(19) 0.21811(16) 0.06891(14) 0.0199(4) Uani 1 1 d . . . S2 S 0.73693(5) 0.28348(5) -0.05709(4) 0.03001(16) Uani 1 1 d . . . N3 N 0.85781(16) 0.12102(13) 0.06870(12) 0.0195(3) Uani 1 1 d D . . H3N H 0.908(2) 0.0922(18) -0.0035(15) 0.042(6) Uiso 1 1 d D . . C4 C 0.89558(18) 0.06047(15) 0.16433(14) 0.0183(4) Uani 1 1 d . . . O4 O 0.98632(14) -0.02380(11) 0.14864(10) 0.0262(3) Uani 1 1 d . . . C5 C 0.82147(18) 0.10335(15) 0.27861(14) 0.0172(4) Uani 1 1 d . . . C6 C 0.72328(18) 0.19671(15) 0.28298(14) 0.0171(4) Uani 1 1 d . . . C1' C 0.63411(19) 0.24038(15) 0.39831(14) 0.0179(4) Uani 1 1 d . . . C2' C 0.5024(2) 0.17716(17) 0.47254(15) 0.0251(4) Uani 1 1 d . . . H2'A H 0.4707 0.1072 0.4500 0.030 Uiso 1 1 calc R . . C3' C 0.4174(2) 0.21638(18) 0.57948(16) 0.0295(5) Uani 1 1 d . . . H3'A H 0.3270 0.1739 0.6294 0.035 Uiso 1 1 calc R . . C4' C 0.4639(2) 0.31701(17) 0.61361(15) 0.0272(5) Uani 1 1 d . . . H4'A H 0.4061 0.3430 0.6873 0.033 Uiso 1 1 calc R . . C5' C 0.5950(2) 0.37985(17) 0.53987(15) 0.0244(4) Uani 1 1 d . . . H5'A H 0.6267 0.4490 0.5634 0.029 Uiso 1 1 calc R . . C6' C 0.68026(19) 0.34281(16) 0.43213(15) 0.0221(4) Uani 1 1 d . . . H6'A H 0.7695 0.3869 0.3816 0.027 Uiso 1 1 calc R . . C1" C 0.85934(19) 0.03523(15) 0.38513(14) 0.0204(4) Uani 1 1 d . . . H1"A H 0.9481 -0.0133 0.3527 0.024 Uiso 1 1 calc R . . H1"B H 0.7807 -0.0285 0.4374 0.024 Uiso 1 1 calc R . . C1"A C 0.88376(19) 0.11671(15) 0.46524(14) 0.0189(4) Uani 1 1 d . . . C2" C 0.79983(19) 0.09459(15) 0.58887(14) 0.0190(4) Uani 1 1 d . . . O2" O 0.69349(14) -0.00017(11) 0.63145(10) 0.0271(3) Uani 1 1 d . . . C3" C 0.8224(2) 0.16618(16) 0.66614(15) 0.0232(4) Uani 1 1 d . . . H3"A H 0.7640 0.1490 0.7505 0.028 Uiso 1 1 calc R . . C4" C 0.9277(2) 0.26003(16) 0.62028(15) 0.0232(4) Uani 1 1 d . . . H4"A H 0.9423 0.3075 0.6734 0.028 Uiso 1 1 calc R . . C4"A C 1.01606(19) 0.28809(16) 0.49474(15) 0.0214(4) Uani 1 1 d . . . C5" C 1.1232(2) 0.38833(18) 0.44490(16) 0.0286(5) Uani 1 1 d . . . H5"A H 1.1395 0.4355 0.4974 0.034 Uiso 1 1 calc R . . C6" C 1.2032(2) 0.41832(19) 0.32313(17) 0.0313(5) Uani 1 1 d . . . H6"A H 1.2718 0.4880 0.2908 0.038 Uiso 1 1 calc R . . C7" C 1.1832(2) 0.34529(18) 0.24590(16) 0.0296(5) Uani 1 1 d . . . H7"A H 1.2393 0.3656 0.1611 0.036 Uiso 1 1 calc R . . C8" C 1.08444(19) 0.24564(17) 0.29108(15) 0.0234(4) Uani 1 1 d . . . H8"A H 1.0753 0.1960 0.2374 0.028 Uiso 1 1 calc R . . C8"A C 0.99469(18) 0.21435(15) 0.41691(14) 0.0191(4) Uani 1 1 d . . . C9" C 0.6039(2) -0.0232(2) 0.75818(16) 0.0391(6) Uani 1 1 d . . . H9"1 H 0.6644 -0.0446 0.8064 0.059 Uiso 1 1 calc R . . H9"2 H 0.5358 -0.0950 0.7771 0.059 Uiso 1 1 calc R . . H9"3 H 0.5500 0.0540 0.7778 0.059 Uiso 1 1 calc R . . C1'" C 0.59369(18) 0.36089(15) 0.18307(15) 0.0194(4) Uani 1 1 d . . . H1'A H 0.5263 0.3560 0.2684 0.023 Uiso 1 1 calc R . . H1'B H 0.5358 0.3487 0.1353 0.023 Uiso 1 1 calc R . . C1A C 0.66566(19) 0.49309(16) 0.13432(14) 0.0201(4) Uani 1 1 d . . . C2'" C 0.8030(2) 0.51977(17) 0.12941(15) 0.0257(4) Uani 1 1 d . . . H2'B H 0.8591 0.4519 0.1517 0.031 Uiso 1 1 calc R . . C3'" C 0.8585(2) 0.64558(18) 0.09186(17) 0.0317(5) Uani 1 1 d . . . H3'B H 0.9518 0.6634 0.0894 0.038 Uiso 1 1 calc R . . C4'" C 0.7780(2) 0.74421(18) 0.05829(16) 0.0313(5) Uani 1 1 d . . . H4'B H 0.8154 0.8301 0.0336 0.038 Uiso 1 1 calc R . . C5'" C 0.6424(2) 0.71799(17) 0.06055(15) 0.0289(5) Uani 1 1 d . . . H5'B H 0.5876 0.7857 0.0362 0.035 Uiso 1 1 calc R . . C6'" C 0.5870(2) 0.59300(16) 0.09828(14) 0.0234(4) Uani 1 1 d . . . H6'B H 0.4942 0.5755 0.0995 0.028 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 N1 0.0204(8) 0.0206(7) 0.0155(7) -0.0054(6) -0.0080(6) 0.0054(6) C2 0.0204(9) 0.0236(9) 0.0168(8) -0.0067(7) -0.0069(7) 0.0005(8) S2 0.0351(3) 0.0394(3) 0.0193(2) -0.0101(2) -0.0141(2) 0.0155(2) N3 0.0223(8) 0.0224(7) 0.0153(7) -0.0070(6) -0.0077(6) 0.0057(6) C4 0.0193(9) 0.0187(8) 0.0186(8) -0.0045(7) -0.0085(7) -0.0006(7) O4 0.0324(8) 0.0271(7) 0.0207(6) -0.0097(5) -0.0110(6) 0.0147(6) C5 0.0189(9) 0.0173(8) 0.0168(8) -0.0052(7) -0.0073(7) -0.0003(7) C6 0.0180(9) 0.0177(8) 0.0165(8) -0.0042(7) -0.0070(7) -0.0015(7) C1' 0.0224(9) 0.0160(8) 0.0165(8) -0.0032(6) -0.0094(7) 0.0059(7) C2' 0.0303(11) 0.0200(9) 0.0233(9) -0.0073(7) -0.0064(8) -0.0013(8) C3' 0.0302(11) 0.0306(10) 0.0211(9) -0.0059(8) -0.0016(8) -0.0034(9) C4' 0.0330(11) 0.0284(10) 0.0190(8) -0.0102(8) -0.0064(8) 0.0065(8) C5' 0.0294(10) 0.0238(9) 0.0253(9) -0.0122(8) -0.0127(8) 0.0047(8) C6' 0.0226(9) 0.0227(9) 0.0222(9) -0.0061(7) -0.0091(7) 0.0025(8) C1" 0.0250(10) 0.0186(9) 0.0189(8) -0.0064(7) -0.0091(7) 0.0046(8) C1"A 0.0221(9) 0.0187(8) 0.0197(8) -0.0059(7) -0.0119(7) 0.0063(7) C2" 0.0217(9) 0.0173(8) 0.0191(8) -0.0029(7) -0.0094(7) 0.0031(8) O2" 0.0315(7) 0.0282(7) 0.0176(6) -0.0026(5) -0.0052(5) -0.0058(6) C3" 0.0290(10) 0.0247(9) 0.0154(8) -0.0044(7) -0.0082(8) 0.0056(8) C4" 0.0300(10) 0.0232(9) 0.0210(9) -0.0101(7) -0.0122(8) 0.0046(8) C4"A 0.0230(9) 0.0217(9) 0.0235(9) -0.0073(7) -0.0124(8) 0.0055(8) C5" 0.0272(10) 0.0311(10) 0.0296(10) -0.0125(8) -0.0098(8) 0.0007(9) C6" 0.0249(10) 0.0330(11) 0.0326(10) -0.0083(8) -0.0056(8) -0.0029(9) C7" 0.0254(10) 0.0376(11) 0.0214(9) -0.0068(8) -0.0033(8) 0.0001(9) C8" 0.0223(10) 0.0287(10) 0.0217(9) -0.0095(7) -0.0090(7) 0.0031(8) C8"A 0.0185(9) 0.0202(9) 0.0192(8) -0.0044(7) -0.0082(7) 0.0062(7) C9" 0.0425(13) 0.0441(12) 0.0216(9) -0.0023(9) -0.0021(9) -0.0153(11) C1'" 0.0168(9) 0.0228(9) 0.0192(8) -0.0059(7) -0.0073(7) 0.0067(7) C1A 0.0224(9) 0.0237(9) 0.0128(8) -0.0055(7) -0.0044(7) 0.0035(8) C2'" 0.0241(10) 0.0276(10) 0.0231(9) -0.0047(7) -0.0069(8) 0.0033(8) C3'" 0.0262(11) 0.0349(11) 0.0305(10) -0.0057(8) -0.0063(8) -0.0054(9) C4'" 0.0371(12) 0.0241(10) 0.0246(9) -0.0030(8) -0.0032(9) -0.0035(9) C5'" 0.0365(11) 0.0248(10) 0.0215(9) -0.0035(7) -0.0082(8) 0.0084(9) C6'" 0.0263(10) 0.0253(10) 0.0184(8) -0.0051(7) -0.0083(7) 0.0062(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 N1 C2 1.378(2) . ? N1 C6 1.407(2) . ? N1 C1'" 1.475(2) . ? C2 N3 1.360(2) . ? C2 S2 1.6580(18) . ? N3 C4 1.380(2) . ? N3 H3N 0.935(15) . ? C4 O4 1.233(2) . ? C4 C5 1.457(2) . ? C5 C6 1.355(2) . ? C5 C1" 1.516(2) . ? C6 C1' 1.498(2) . ? C1' C2' 1.393(2) . ? C1' C6' 1.395(2) . ? C2' C3' 1.388(2) . ? C2' H2'A 0.9500 . ? C3' C4' 1.382(3) . ? C3' H3'A 0.9500 . ? C4' C5' 1.386(3) . ? C4' H4'A 0.9500 . ? C5' C6' 1.386(2) . ? C5' H5'A 0.9500 . ? C6' H6'A 0.9500 . ? C1" C1"A 1.517(2) . ? C1" H1"A 0.9900 . ? C1" H1"B 0.9900 . ? C1"A C2" 1.389(2) . ? C1"A C8"A 1.424(2) . ? C2" O2" 1.376(2) . ? C2" C3" 1.407(2) . ? O2" C9" 1.431(2) . ? C3" C4" 1.361(2) . ? C3" H3"A 0.9500 . ? C4" C4"A 1.417(2) . ? C4" H4"A 0.9500 . ? C4"A C5" 1.419(2) . ? C4"A C8"A 1.423(2) . ? C5" C6" 1.364(3) . ? C5" H5"A 0.9500 . ? C6" C7" 1.406(3) . ? C6" H6"A 0.9500 . ? C7" C8" 1.364(3) . ? C7" H7"A 0.9500 . ? C8" C8"A 1.424(2) . ? C8" H8"A 0.9500 . ? C9" H9"1 0.9800 . ? C9" H9"2 0.9800 . ? C9" H9"3 0.9800 . ? C1'" C1A 1.512(2) . ? C1'" H1'A 0.9900 . ? C1'" H1'B 0.9900 . ? C1A C6'" 1.388(3) . ? C1A C2'" 1.394(3) . ? C2'" C3'" 1.393(3) . ? C2'" H2'B 0.9500 . ? C3'" C4'" 1.380(3) . ? C3'" H3'B 0.9500 . ? C4'" C5'" 1.387(3) . ? C4'" H4'B 0.9500 . ? C5'" C6'" 1.385(2) . ? C5'" H5'B 0.9500 . ? C6'" H6'B 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 C2 N1 C6 121.85(15) . . ? C2 N1 C1'" 117.15(14) . . ? C6 N1 C1'" 120.99(13) . . ? N3 C2 N1 115.33(15) . . ? N3 C2 S2 120.42(12) . . ? N1 C2 S2 124.25(14) . . ? C2 N3 C4 127.21(14) . . ? C2 N3 H3N 119.4(14) . . ? C4 N3 H3N 113.3(14) . . ? O4 C4 N3 119.49(15) . . ? O4 C4 C5 125.05(16) . . ? N3 C4 C5 115.46(15) . . ? C6 C5 C4 118.74(16) . . ? C6 C5 C1" 125.30(15) . . ? C4 C5 C1" 115.93(15) . . ? C5 C6 N1 121.32(14) . . ? C5 C6 C1' 122.58(15) . . ? N1 C6 C1' 116.07(15) . . ? C2' C1' C6' 119.74(15) . . ? C2' C1' C6 118.95(14) . . ? C6' C1' C6 121.31(14) . . ? C3' C2' C1' 120.00(16) . . ? C3' C2' H2'A 120.0 . . ? C1' C2' H2'A 120.0 . . ? C4' C3' C2' 120.25(17) . . ? C4' C3' H3'A 119.9 . . ? C2' C3' H3'A 119.9 . . ? C3' C4' C5' 119.78(16) . . ? C3' C4' H4'A 120.1 . . ? C5' C4' H4'A 120.1 . . ? C6' C5' C4' 120.66(16) . . ? C6' C5' H5'A 119.7 . . ? C4' C5' H5'A 119.7 . . ? C5' C6' C1' 119.56(16) . . ? C5' C6' H6'A 120.2 . . ? C1' C6' H6'A 120.2 . . ? C5 C1" C1"A 117.76(13) . . ? C5 C1" H1"A 107.9 . . ? C1"A C1" H1"A 107.9 . . ? C5 C1" H1"B 107.9 . . ? C1"A C1" H1"B 107.9 . . ? H1"A C1" H1"B 107.2 . . ? C2" C1"A C8"A 118.63(15) . . ? C2" C1"A C1" 120.08(14) . . ? C8"A C1"A C1" 121.27(14) . . ? O2" C2" C1"A 116.63(15) . . ? O2" C2" C3" 121.92(14) . . ? C1"A C2" C3" 121.44(15) . . ? C2" O2" C9" 117.69(14) . . ? C4" C3" C2" 120.15(15) . . ? C4" C3" H3"A 119.9 . . ? C2" C3" H3"A 119.9 . . ? C3" C4" C4"A 121.12(16) . . ? C3" C4" H4"A 119.4 . . ? C4"A C4" H4"A 119.4 . . ? C4" C4"A C5" 121.79(16) . . ? C4" C4"A C8"A 118.72(15) . . ? C5" C4"A C8"A 119.49(15) . . ? C6" C5" C4"A 121.32(17) . . ? C6" C5" H5"A 119.3 . . ? C4"A C5" H5"A 119.3 . . ? C5" C6" C7" 119.41(17) . . ? C5" C6" H6"A 120.3 . . ? C7" C6" H6"A 120.3 . . ? C8" C7" C6" 120.87(16) . . ? C8" C7" H7"A 119.6 . . ? C6" C7" H7"A 119.6 . . ? C7" C8" C8"A 121.50(16) . . ? C7" C8" H8"A 119.3 . . ? C8"A C8" H8"A 119.3 . . ? C4"A C8"A C8" 117.32(15) . . ? C4"A C8"A C1"A 119.93(14) . . ? C8" C8"A C1"A 122.72(15) . . ? O2" C9" H9"1 109.5 . . ? O2" C9" H9"2 109.5 . . ? H9"1 C9" H9"2 109.5 . . ? O2" C9" H9"3 109.5 . . ? H9"1 C9" H9"3 109.5 . . ? H9"2 C9" H9"3 109.5 . . ? N1 C1'" C1A 113.80(14) . . ? N1 C1'" H1'A 108.8 . . ? C1A C1'" H1'A 108.8 . . ? N1 C1'" H1'B 108.8 . . ? C1A C1'" H1'B 108.8 . . ? H1'A C1'" H1'B 107.7 . . ? C6'" C1A C2'" 119.01(16) . . ? C6'" C1A C1'" 117.62(16) . . ? C2'" C1A C1'" 123.29(17) . . ? C3'" C2'" C1A 120.26(19) . . ? C3'" C2'" H2'B 119.9 . . ? C1A C2'" H2'B 119.9 . . ? C4'" C3'" C2'" 120.04(19) . . ? C4'" C3'" H3'B 120.0 . . ? C2'" C3'" H3'B 120.0 . . ? C3'" C4'" C5'" 120.00(18) . . ? C3'" C4'" H4'B 120.0 . . ? C5'" C4'" H4'B 120.0 . . ? C6'" C5'" C4'" 119.97(19) . . ? C6'" C5'" H5'B 120.0 . . ? C4'" C5'" H5'B 120.0 . . ? C5'" C6'" C1A 120.69(18) . . ? C5'" C6'" H6'B 119.7 . . ? C1A C6'" H6'B 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 N3 0.1(2) . . . . ? C1'" N1 C2 N3 179.76(13) . . . . ? C6 N1 C2 S2 -179.88(12) . . . . ? C1'" N1 C2 S2 -0.2(2) . . . . ? N1 C2 N3 C4 -2.6(2) . . . . ? S2 C2 N3 C4 177.40(13) . . . . ? C2 N3 C4 O4 -177.75(15) . . . . ? C2 N3 C4 C5 2.5(2) . . . . ? O4 C4 C5 C6 -179.63(15) . . . . ? N3 C4 C5 C6 0.1(2) . . . . ? O4 C4 C5 C1" -1.2(2) . . . . ? N3 C4 C5 C1" 178.54(13) . . . . ? C4 C5 C6 N1 -2.4(2) . . . . ? C1" C5 C6 N1 179.41(14) . . . . ? C4 C5 C6 C1' 175.51(14) . . . . ? C1" C5 C6 C1' -2.7(2) . . . . ? C2 N1 C6 C5 2.3(2) . . . . ? C1'" N1 C6 C5 -177.34(14) . . . . ? C2 N1 C6 C1' -175.68(14) . . . . ? C1'" N1 C6 C1' 4.7(2) . . . . ? C5 C6 C1' C2' -88.4(2) . . . . ? N1 C6 C1' C2' 89.54(19) . . . . ? C5 C6 C1' C6' 91.8(2) . . . . ? N1 C6 C1' C6' -90.2(2) . . . . ? C6' C1' C2' C3' 0.2(3) . . . . ? C6 C1' C2' C3' -179.61(18) . . . . ? C1' C2' C3' C4' -0.8(3) . . . . ? C2' C3' C4' C5' 0.8(3) . . . . ? C3' C4' C5' C6' 0.0(3) . . . . ? C4' C5' C6' C1' -0.6(3) . . . . ? C2' C1' C6' C5' 0.6(3) . . . . ? C6 C1' C6' C5' -179.66(17) . . . . ? C6 C5 C1" C1"A -45.3(2) . . . . ? C4 C5 C1" C1"A 136.46(15) . . . . ? C5 C1" C1"A C2" 121.57(18) . . . . ? C5 C1" C1"A C8"A -60.2(2) . . . . ? C8"A C1"A C2" O2" 179.68(15) . . . . ? C1" C1"A C2" O2" -2.0(2) . . . . ? C8"A C1"A C2" C3" 0.0(3) . . . . ? C1" C1"A C2" C3" 178.27(16) . . . . ? C1"A C2" O2" C9" -178.93(17) . . . . ? C3" C2" O2" C9" 0.8(3) . . . . ? O2" C2" C3" C4" -179.32(17) . . . . ? C1"A C2" C3" C4" 0.4(3) . . . . ? C2" C3" C4" C4"A 0.3(3) . . . . ? C3" C4" C4"A C5" 177.95(18) . . . . ? C3" C4" C4"A C8"A -1.2(3) . . . . ? C4" C4"A C5" C6" -177.03(19) . . . . ? C8"A C4"A C5" C6" 2.1(3) . . . . ? C4"A C5" C6" C7" -2.5(3) . . . . ? C5" C6" C7" C8" 0.4(3) . . . . ? C6" C7" C8" C8"A 2.1(3) . . . . ? C4" C4"A C8"A C8" 179.52(17) . . . . ? C5" C4"A C8"A C8" 0.3(3) . . . . ? C4" C4"A C8"A C1"A 1.5(3) . . . . ? C5" C4"A C8"A C1"A -177.64(17) . . . . ? C7" C8" C8"A C4"A -2.4(3) . . . . ? C7" C8" C8"A C1"A 175.50(18) . . . . ? C2" C1"A C8"A C4"A -0.9(3) . . . . ? C1" C1"A C8"A C4"A -179.21(15) . . . . ? C2" C1"A C8"A C8" -178.80(17) . . . . ? C1" C1"A C8"A C8" 2.9(3) . . . . ? C2 N1 C1'" C1A -80.41(18) . . . . ? C6 N1 C1'" C1A 99.28(17) . . . . ? N1 C1'" C1A C6'" 159.81(14) . . . . ? N1 C1'" C1A C2'" -23.3(2) . . . . ? C6'" C1A C2'" C3'" 1.7(2) . . . . ? C1'" C1A C2'" C3'" -175.19(15) . . . . ? C1A C2'" C3'" C4'" -0.6(3) . . . . ? C2'" C3'" C4'" C5'" -0.8(3) . . . . ? C3'" C4'" C5'" C6'" 1.0(3) . . . . ? C4'" C5'" C6'" C1A 0.1(2) . . . . ? C2'" C1A C6'" C5'" -1.5(2) . . . . ? C1'" C1A C6'" C5'" 175.59(14) . . . . ? 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 N3 H3N O4 0.935(15) 1.943(16) 2.8772(19) 177.1(19) 2_755 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.235 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.049