# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondence ; Dr. A.L. Spek ; _publ_contact_author_address # Address of author for correspondence ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; _publ_contact_author_email 'spea@chem.uu.nl' _publ_contact_author_fax '+31 30 2533940' _publ_contact_author_phone '+31 30 2532538' _publ_section_acknowledgements ; This work was supported in part by the Netherlands Foundation for Chemical Research (SON) with financial aid from the Netherlands Organization for Scientific Research (NWO) ; #=============================================================================== data_s1686a #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_moiety '2(C11 H17 N O2 S), 0.5(C6 H6)' _chemical_formula_sum 'C25 H37 N2 O4 S2' _chemical_formula_weight 493.70 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 5.0885(3) _cell_length_b 15.5224(17) _cell_length_c 16.5379(16) _cell_angle_alpha 102.839(8) _cell_angle_beta 95.947(6) _cell_angle_gamma 94.025(7) _cell_volume 1260.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 0.24 _exptl_absorpt_correction_type none #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite' _diffrn_measurement_device_type 'CAD4T' _diffrn_measurement_method 'omega-scan' # number of measured reflections (redundant set) _diffrn_reflns_number 7139 _diffrn_reflns_av_R_equivalents 0.1155 _diffrn_reflns_av_sigmaI/netI 0.1123 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 27.50 # number of unique reflections _reflns_number_total 5799 # number of observed reflections (> n sig(I)) _reflns_number_gt 3386 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Locally modified CAD4-Version 5 Software' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc ' _refine_ls_weighting_details 'CALC W=1/[^2^(FO^2^)+(0.1000P)^2^+4.6080P] WHERE P=(FO^2^+2FC^2^)/3' _refine_ls_hydrogen_treatment 'H-atom refinement: see text ' _refine_ls_extinction_method none _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack none _refine_ls_number_reflns 5799 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1689 _refine_ls_R_factor_gt 0.1010 _refine_ls_wR_factor_ref 0.2801 _refine_ls_wR_factor_gt 0.2367 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.006 _refine_diff_density_max 1.326 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.099 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv S1' S Uani 0.8130(3) 0.25987(9) 0.19739(9) 1.000 0.0322(4) O1 O Uani 0.2625(9) 0.7514(3) 0.5077(3) 1.000 0.0529(17) O1' O Uani 1.1120(7) 0.2643(3) 0.1982(2) 1.000 0.0353(11) N1 N Uani 0.2975(12) 0.7452(4) 0.4250(4) 1.000 0.060(2) C1 C Uani 0.4103(19) 0.6704(6) 0.4000(5) 1.000 0.076(3) C2 C Uani 0.493(2) 0.6020(6) 0.4462(5) 1.000 0.084(4) C2' C Uani 0.7619(10) 0.3037(4) 0.3041(3) 1.000 0.0314(17) C3 C Uani 0.7456(17) 0.5727(5) 0.4284(4) 1.000 0.062(3) C3' C Uani 0.9157(11) 0.3941(4) 0.3412(3) 1.000 0.0340(17) C4 C Uani 0.7622(16) 0.5434(4) 0.3351(4) 1.000 0.052(2) C4' C Uani 0.8360(11) 0.4650(4) 0.2972(3) 1.000 0.0337(17) C5 C Uani 0.6939(19) 0.6178(5) 0.2928(5) 1.000 0.072(3) C5' C Uani 0.8707(11) 0.4398(3) 0.2047(3) 1.000 0.0303(17) C6 C Uani 0.444(2) 0.6487(6) 0.3082(6) 1.000 0.088(4) C6' C Uani 0.7101(11) 0.3529(4) 0.1585(3) 1.000 0.0332(17) S11' S Uani 0.7733(3) -0.08750(10) 0.56513(9) 1.000 0.0361(4) O11 O Uani 0.2345(9) 0.1582(3) 1.0547(3) 1.000 0.0559(17) O11' O Uani 1.0705(7) -0.0919(3) 0.5680(2) 1.000 0.0375(11) N11 N Uani 0.2904(10) 0.2086(4) 0.9991(4) 1.000 0.051(2) C11 C Uani 0.3622(10) 0.1532(4) 0.9310(4) 1.000 0.0414(19) C12 C Uani 0.3917(11) 0.0576(4) 0.9159(4) 1.000 0.0398(19) C12' C Uani 0.6898(11) -0.1193(4) 0.6582(4) 1.000 0.0380(19) C13 C Uani 0.6772(11) 0.0402(4) 0.8957(4) 1.000 0.0384(19) C13' C Uani 0.8584(11) -0.0653(4) 0.7365(4) 1.000 0.0330(17) C14 C Uani 0.7404(10) 0.0787(4) 0.8234(3) 1.000 0.0304(16) C14' C Uani 0.8204(10) 0.0326(3) 0.7529(3) 1.000 0.0276(16) C15 C Uani 0.7111(10) 0.1775(4) 0.8423(4) 1.000 0.0362(17) C15' C Uani 0.8903(10) 0.0720(4) 0.6818(3) 1.000 0.0307(17) C16 C Uani 0.4329(11) 0.1976(4) 0.8643(4) 1.000 0.0406(17) C16' C Uani 0.7252(10) 0.0277(4) 0.5990(3) 1.000 0.0334(17) C20 C Uani 0.102(3) 0.5758(7) 0.0523(7) 1.000 0.093(4) C21 C Uani 0.118(3) 0.4255(8) -0.0006(8) 1.000 0.092(5) C22 C Uani 0.2182(16) 0.5008(12) 0.0513(7) 1.000 0.090(5) H1 H Uiso 0.14910 0.81800 0.53510 1.000 0.10 H2A H Uiso 0.50030 0.62680 0.50580 1.000 0.1010 H2B H Uiso 0.35980 0.55140 0.43130 1.000 0.1010 H3A H Uiso 0.77880 0.52360 0.45420 1.000 0.0750 H3B H Uiso 0.88300 0.62070 0.45280 1.000 0.0750 H5A H Uiso 0.83060 0.66710 0.31230 1.000 0.0860 H5B H Uiso 0.69430 0.59700 0.23300 1.000 0.0860 H6A H Uiso 0.30400 0.60370 0.27840 1.000 0.1060 H6B H Uiso 0.42420 0.70140 0.28660 1.000 0.1060 H21' H Uiso 0.57410 0.30910 0.30680 1.000 0.0380 H22' H Uiso 0.81640 0.26240 0.33730 1.000 0.0380 H31' H Uiso 0.88880 0.41260 0.39950 1.000 0.0410 H32' H Uiso 1.10360 0.38840 0.33900 1.000 0.0410 H51' H Uiso 1.05710 0.43440 0.19920 1.000 0.0370 H52' H Uiso 0.81660 0.48700 0.17880 1.000 0.0370 H61' H Uiso 0.72990 0.34260 0.09950 1.000 0.0400 H62' H Uiso 0.52370 0.35800 0.16430 1.000 0.0400 H11 H Uiso 0.12530 0.20640 1.09670 1.000 0.8(4) H12A H Uiso 0.26380 0.02570 0.86940 1.000 0.0480 H12B H Uiso 0.35740 0.03620 0.96500 1.000 0.0480 H12C H Uiso 0.50430 -0.11160 0.66350 1.000 0.0460 H12D H Uiso 0.71320 -0.18170 0.65310 1.000 0.0460 H13A H Uiso 0.81390 -0.08790 0.78400 1.000 0.0400 H13B H Uiso 1.04390 -0.07290 0.73110 1.000 0.0400 H13C H Uiso 0.80360 0.06690 0.94440 1.000 0.0460 H13D H Uiso 0.69220 -0.02320 0.88210 1.000 0.0460 H15A H Uiso 1.07660 0.06660 0.67590 1.000 0.0370 H15B H Uiso 0.86510 0.13470 0.69510 1.000 0.0370 H15C H Uiso 0.74530 0.20040 0.79400 1.000 0.0430 H15D H Uiso 0.84200 0.20750 0.88870 1.000 0.0430 H16A H Uiso 0.77200 0.05850 0.55670 1.000 0.0400 H16B H Uiso 0.53900 0.03330 0.60470 1.000 0.0400 H16C H Uiso 0.42830 0.26120 0.88320 1.000 0.0480 H16D H Uiso 0.30430 0.17690 0.81490 1.000 0.0480 H20 H Uiso 0.17390 0.62860 0.08900 1.000 0.1120 H21 H Uiso 0.19970 0.37370 -0.00090 1.000 0.1100 H22 H Uiso 0.37140 0.50180 0.08760 1.000 0.1080 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 S1' 0.0291(7) 0.0277(7) 0.0369(7) 0.0016(5) 0.0064(5) -0.0006(5) O1 0.053(3) 0.053(3) 0.051(3) 0.013(2) 0.006(2) -0.009(2) O1' 0.0263(18) 0.040(2) 0.039(2) 0.0023(18) 0.0108(16) 0.0112(16) N1 0.066(4) 0.071(4) 0.039(3) 0.007(3) 0.009(3) -0.013(3) C1 0.103(7) 0.064(5) 0.072(6) 0.017(4) 0.035(5) 0.050(5) C2 0.132(8) 0.084(6) 0.052(5) 0.018(4) 0.048(5) 0.054(6) C2' 0.029(3) 0.036(3) 0.034(3) 0.013(2) 0.013(2) 0.006(2) C3 0.097(6) 0.058(4) 0.036(4) 0.009(3) 0.021(4) 0.023(4) C3' 0.039(3) 0.034(3) 0.031(3) 0.007(2) 0.011(2) 0.009(2) C4 0.091(5) 0.039(3) 0.035(3) 0.014(3) 0.023(3) 0.022(3) C4' 0.045(3) 0.031(3) 0.027(3) 0.009(2) 0.007(2) 0.006(2) C5 0.125(8) 0.047(4) 0.056(5) 0.019(4) 0.033(5) 0.035(5) C5' 0.033(3) 0.029(3) 0.030(3) 0.005(2) 0.012(2) 0.004(2) C6 0.130(9) 0.080(6) 0.076(6) 0.033(5) 0.038(6) 0.069(6) C6' 0.031(3) 0.036(3) 0.032(3) 0.006(2) 0.006(2) 0.002(2) S11' 0.0268(7) 0.0416(8) 0.0345(7) -0.0028(6) 0.0070(5) -0.0013(6) O11 0.045(3) 0.053(3) 0.072(3) 0.017(3) 0.010(2) 0.009(2) O11' 0.0274(19) 0.041(2) 0.040(2) -0.0022(18) 0.0108(16) 0.0031(16) N11 0.032(3) 0.059(4) 0.067(4) 0.031(3) -0.004(3) -0.006(2) C11 0.023(3) 0.064(4) 0.031(3) -0.005(3) 0.003(2) 0.013(3) C12 0.030(3) 0.057(4) 0.035(3) 0.015(3) 0.009(2) 0.000(3) C12' 0.029(3) 0.034(3) 0.052(4) 0.007(3) 0.017(3) 0.001(2) C13 0.033(3) 0.053(4) 0.034(3) 0.014(3) 0.013(2) 0.012(3) C13' 0.033(3) 0.032(3) 0.037(3) 0.011(2) 0.010(2) 0.006(2) C14 0.022(2) 0.038(3) 0.032(3) 0.008(2) 0.005(2) 0.006(2) C14' 0.023(2) 0.033(3) 0.029(3) 0.010(2) 0.006(2) 0.004(2) C15 0.027(3) 0.039(3) 0.039(3) 0.000(2) 0.007(2) 0.003(2) C15' 0.032(3) 0.030(3) 0.030(3) 0.004(2) 0.010(2) 0.003(2) C16 0.031(3) 0.040(3) 0.047(3) -0.001(3) 0.008(2) 0.009(2) C16' 0.027(3) 0.044(3) 0.032(3) 0.011(2) 0.010(2) 0.006(2) C20 0.145(10) 0.050(5) 0.077(7) -0.006(5) 0.059(7) -0.047(6) C21 0.136(10) 0.086(7) 0.101(8) 0.068(7) 0.089(8) 0.076(7) C22 0.039(4) 0.171(12) 0.071(6) 0.049(8) 0.015(4) 0.003(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1' O1' 1.517(4) . . yes S1' C2' 1.798(5) . . yes S1' C6' 1.795(6) . . yes S11' C12' 1.799(7) . . yes S11' C16' 1.793(6) . . yes S11' O11' 1.515(4) . . yes O1 N1 1.381(8) . . yes O1 H1 1.2397 . . no O11 N11 1.372(8) . . yes O11 H11 1.1218 . . no N1 C1 1.333(11) . . yes N11 C11 1.357(9) . . yes C1 C2 1.498(13) . . no C1 C6 1.511(13) . . no C2 C3 1.431(13) . . no C2' C3' 1.524(8) . . no C3 C4 1.522(9) . . no C3' C4' 1.504(8) . . no C4 C5 1.520(10) . . no C4 C4' 1.337(9) . . no C4' C5' 1.524(7) . . no C5 C6 1.418(14) . . no C5' C6' 1.526(8) . . no C2 H2A 0.9710 . . no C2 H2B 0.9704 . . no C2' H22' 0.9691 . . no C2' H21' 0.9699 . . no C3 H3B 0.9704 . . no C3 H3A 0.9691 . . no C3' H32' 0.9700 . . no C3' H31' 0.9699 . . no C5 H5A 0.9709 . . no C5 H5B 0.9700 . . no C5' H51' 0.9698 . . no C5' H52' 0.9692 . . no C6 H6B 0.9700 . . no C6 H6A 0.9709 . . no C6' H62' 0.9701 . . no C6' H61' 0.9701 . . no C11 C12 1.470(9) . . no C11 C16 1.485(9) . . no C12 C13 1.553(8) . . no C12' C13' 1.517(9) . . no C13 C14 1.503(8) . . no C13' C14' 1.513(8) . . no C14 C14' 1.344(7) . . no C14 C15 1.517(9) . . no C14' C15' 1.503(7) . . no C15 C16 1.534(8) . . no C15' C16' 1.522(7) . . no C12 H12A 0.9705 . . no C12 H12B 0.9702 . . no C12' H12C 0.9702 . . no C12' H12D 0.9703 . . no C13 H13C 0.9701 . . no C13 H13D 0.9699 . . no C13' H13A 0.9693 . . no C13' H13B 0.9702 . . no C15 H15C 0.9701 . . no C15 H15D 0.9701 . . no C15' H15A 0.9705 . . no C15' H15B 0.9697 . . no C16 H16C 0.9698 . . no C16 H16D 0.9705 . . no C16' H16A 0.9705 . . no C16' H16B 0.9698 . . no C20 C22 1.34(2) . . no C20 C21 1.33(2) . 2_565 no C21 C22 1.32(2) . . no C20 H20 0.9299 . . no C21 H21 0.9300 . . no C22 H22 0.9303 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1' S1' C2' 105.0(2) . . . yes O1' S1' C6' 106.0(3) . . . yes C2' S1' C6' 96.3(3) . . . yes C12' S11' C16' 96.4(3) . . . yes O11' S11' C16' 106.1(3) . . . yes O11' S11' C12' 104.8(2) . . . yes N1 O1 H1 110.70 . . . no N11 O11 H11 98.87 . . . no O1 N1 C1 106.6(6) . . . yes O11 N11 C11 107.3(5) . . . yes C2 C1 C6 115.0(8) . . . no N1 C1 C2 130.9(7) . . . yes N1 C1 C6 114.0(8) . . . yes C1 C2 C3 112.7(8) . . . no S1' C2' C3' 112.6(4) . . . yes C2 C3 C4 112.6(7) . . . no C2' C3' C4' 113.7(4) . . . no C3 C4 C4' 124.6(6) . . . no C3 C4 C5 109.8(6) . . . no C4' C4 C5 125.5(6) . . . no C3' C4' C5' 111.7(5) . . . no C3' C4' C4 124.5(5) . . . no C4 C4' C5' 123.6(5) . . . no C4 C5 C6 113.5(8) . . . no C4' C5' C6' 112.9(4) . . . no C1 C6 C5 112.7(8) . . . no S1' C6' C5' 112.3(4) . . . yes C1 C2 H2B 108.97 . . . no C3 C2 H2A 109.18 . . . no C3 C2 H2B 109.19 . . . no C1 C2 H2A 108.96 . . . no H2A C2 H2B 107.72 . . . no S1' C2' H22' 109.04 . . . no C3' C2' H21' 109.02 . . . no S1' C2' H21' 109.01 . . . no C3' C2' H22' 109.12 . . . no H21' C2' H22' 107.95 . . . no C4 C3 H3B 108.97 . . . no H3A C3 H3B 107.92 . . . no C2 C3 H3A 109.11 . . . no C2 C3 H3B 109.06 . . . no C4 C3 H3A 109.10 . . . no C2' C3' H32' 108.87 . . . no C4' C3' H31' 108.81 . . . no C4' C3' H32' 108.79 . . . no C2' C3' H31' 108.78 . . . no H31' C3' H32' 107.71 . . . no H5A C5 H5B 107.71 . . . no C6 C5 H5A 108.82 . . . no C4 C5 H5A 108.86 . . . no C4 C5 H5B 108.94 . . . no C6 C5 H5B 108.87 . . . no H51' C5' H52' 107.82 . . . no C4' C5' H52' 108.93 . . . no C6' C5' H51' 108.99 . . . no C4' C5' H51' 109.03 . . . no C6' C5' H52' 109.02 . . . no C1 C6 H6B 109.00 . . . no C5 C6 H6A 109.21 . . . no C5 C6 H6B 109.24 . . . no H6A C6 H6B 107.61 . . . no C1 C6 H6A 108.98 . . . no C5' C6' H61' 109.12 . . . no C5' C6' H62' 109.12 . . . no S1' C6' H61' 109.17 . . . no S1' C6' H62' 109.14 . . . no H61' C6' H62' 107.91 . . . no N11 C11 C12 129.4(6) . . . yes N11 C11 C16 114.3(6) . . . yes C12 C11 C16 116.1(5) . . . no C11 C12 C13 109.8(5) . . . no S11' C12' C13' 112.5(4) . . . yes C12 C13 C14 110.4(5) . . . no C12' C13' C14' 112.9(5) . . . no C13 C14 C15 110.6(5) . . . no C14' C14 C15 124.6(5) . . . no C13 C14 C14' 124.7(5) . . . no C13' C14' C15' 111.6(4) . . . no C14 C14' C15' 124.5(5) . . . no C13' C14' C14 123.9(5) . . . no C14 C15 C16 111.8(5) . . . no C14' C15' C16' 113.1(5) . . . no C11 C16 C15 110.3(5) . . . no S11' C16' C15' 112.7(4) . . . yes C11 C12 H12A 109.69 . . . no C11 C12 H12B 109.73 . . . no C13 C12 H12A 109.64 . . . no C13 C12 H12B 109.74 . . . no H12A C12 H12B 108.21 . . . no S11' C12' H12C 109.09 . . . no S11' C12' H12D 109.14 . . . no C13' C12' H12C 109.02 . . . no C13' C12' H12D 109.10 . . . no H12C C12' H12D 107.88 . . . no C12 C13 H13C 109.53 . . . no C12 C13 H13D 109.54 . . . no C14 C13 H13C 109.58 . . . no C14 C13 H13D 109.65 . . . no H13C C13 H13D 108.10 . . . no C12' C13' H13A 108.99 . . . no C12' C13' H13B 108.98 . . . no C14' C13' H13A 109.06 . . . no C14' C13' H13B 109.06 . . . no H13A C13' H13B 107.73 . . . no C14 C15 H15C 109.21 . . . no C14 C15 H15D 109.22 . . . no C16 C15 H15C 109.30 . . . no C16 C15 H15D 109.24 . . . no H15C C15 H15D 107.98 . . . no C14' C15' H15A 108.90 . . . no C14' C15' H15B 108.93 . . . no C16' C15' H15A 108.92 . . . no C16' C15' H15B 109.02 . . . no H15A C15' H15B 107.81 . . . no C11 C16 H16C 109.60 . . . no C11 C16 H16D 109.71 . . . no C15 C16 H16C 109.59 . . . no C15 C16 H16D 109.58 . . . no H16C C16 H16D 108.05 . . . no S11' C16' H16A 109.12 . . . no S11' C16' H16B 109.12 . . . no C15' C16' H16A 108.98 . . . no C15' C16' H16B 109.03 . . . no H16A C16' H16B 107.77 . . . no C21 C20 C22 119.7(11) 2_565 . . no C20 C21 C22 119.5(13) 2_565 . . no C20 C22 C21 120.8(11) . . . no C22 C20 H20 120.29 . . . no C21 C20 H20 119.96 2_565 . . no C22 C21 H21 120.30 . . . no C20 C21 H21 120.24 2_565 . . no C20 C22 H22 119.61 . . . no C21 C22 H22 119.59 . . . no 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 O1' S1' C2' C3' 52.3(5) . . . . no C6' S1' C2' C3' -56.1(4) . . . . no O1' S1' C6' C5' -50.7(4) . . . . no C2' S1' C6' C5' 56.8(4) . . . . no C12' S11' C16' C15' 55.6(4) . . . . no O11' S11' C12' C13' 52.7(5) . . . . no C16' S11' C12' C13' -55.9(5) . . . . no O11' S11' C16' C15' -51.9(4) . . . . no O1 N1 C1 C2 -0.3(12) . . . . no O1 N1 C1 C6 175.4(7) . . . . no O11 N11 C11 C16 -179.4(5) . . . . no O11 N11 C11 C12 -2.6(8) . . . . no C6 C1 C2 C3 46.7(11) . . . . no C2 C1 C6 C5 -45.9(11) . . . . no N1 C1 C2 C3 -137.7(10) . . . . no N1 C1 C6 C5 137.7(8) . . . . no C1 C2 C3 C4 -51.7(9) . . . . no S1' C2' C3' C4' 61.9(5) . . . . no C2 C3 C4 C5 55.3(9) . . . . no C2 C3 C4 C4' -127.1(9) . . . . no C2' C3' C4' C5' -58.0(6) . . . . no C2' C3' C4' C4 126.6(7) . . . . no C3 C4 C5 C6 -55.0(9) . . . . no C4' C4 C5 C6 127.4(9) . . . . no C3 C4 C4' C5' -175.3(6) . . . . no C5 C4 C4' C5' 1.9(11) . . . . no C3 C4 C4' C3' -0.5(11) . . . . no C5 C4 C4' C3' 176.8(7) . . . . no C3' C4' C5' C6' 58.5(6) . . . . no C4 C4' C5' C6' -126.1(7) . . . . no C4 C5 C6 C1 50.4(10) . . . . no C4' C5' C6' S1' -62.9(5) . . . . no C16 C11 C12 C13 53.8(7) . . . . no N11 C11 C12 C13 -122.9(6) . . . . no N11 C11 C16 C15 125.1(6) . . . . no C12 C11 C16 C15 -52.1(7) . . . . no C11 C12 C13 C14 -55.3(7) . . . . no S11' C12' C13' C14' 62.6(6) . . . . no C12 C13 C14 C15 57.7(6) . . . . no C12 C13 C14 C14' -124.4(6) . . . . no C12' C13' C14' C14 122.0(6) . . . . no C12' C13' C14' C15' -59.5(6) . . . . no C13 C14 C14' C13' -0.1(8) . . . . no C13 C14 C14' C15' -178.3(5) . . . . no C13 C14 C15 C16 -56.5(6) . . . . no C14' C14 C15 C16 125.6(6) . . . . no C15 C14 C14' C13' 177.6(5) . . . . no C15 C14 C14' C15' -0.6(8) . . . . no C13' C14' C15' C16' 59.2(6) . . . . no C14 C14' C15' C16' -122.4(6) . . . . no C14 C15 C16 C11 51.7(7) . . . . no C14' C15' C16' S11' -62.3(5) . . . . no C21 C20 C22 C21 0.3(19) 2_565 . . . no C22 C20 C21 C22 0(2) . . 2_565 2_565 no C20 C21 C22 C20 0(2) 2_565 . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S11' O1 3.381(5) . 1_545 no S1' H11 2.4711 . 1_654 no S11' H1 2.5143 . 1_645 no O1 O11' 2.706(6) . 1_465 no O1 C12' 3.316(8) . 1_565 no O1 S11' 3.381(5) . 1_565 no O1 C2' 3.418(7) . 2_666 no O1' O11 2.729(6) . 1_654 no O11 O1' 2.729(6) . 1_456 no O11 C13 3.406(8) . 2_657 no O11' C16' 3.373(6) . 2_756 no O11' O1 2.706(6) . 1_645 no O1 H3B 2.6339 . 1_455 no O1 H2A 2.3485 . . no O1 H22' 2.6876 . 2_666 no O1' H32' 2.6783 . . no O1' H21' 2.7529 . 1_655 no O1' H11 1.7296 . 1_654 no O1' H51' 2.6711 . . no O1' H13A 2.8647 . 2_756 no O1' H62' 2.6451 . 1_655 no O11 H12B 2.2996 . . no O11 H13C 2.7802 . 1_455 no O11 H13D 2.5739 . 2_657 no O11' H12C 2.6547 . 1_655 no O11' H15A 2.6954 . . no O11' H16B 2.8903 . 1_655 no O11' H13B 2.6662 . . no O11' H16A 2.4338 . 2_756 no O11' H1 1.4824 . 1_645 no N1 H3B 2.9014 . 1_455 no N1 H5A 2.8744 . 1_455 no N11 H21 2.6357 . 1_556 no N11 H15D 2.7672 . 1_455 no C2' O1 3.418(7) . 2_666 no C5' C22 3.496(13) . 1_655 no C11 C14 3.453(8) . 1_455 no C11 C15 3.562(8) . 1_455 no C12 C14 3.571(8) . 1_455 no C12' O1 3.316(8) . 1_545 no C13 O11 3.406(8) . 2_657 no C14 C12 3.571(8) . 1_655 no C14 C11 3.453(8) . 1_655 no C15 C11 3.562(8) . 1_655 no C16' O11' 3.373(6) . 2_756 no C22 C22 3.479(13) . 2_665 no C22 C5' 3.496(13) . 1_455 no C1 H3B 3.0085 . 1_455 no C3 H31' 2.5950 . . no C3' H3A 2.6106 . . no C5 H52' 2.6052 . . no C5' H5B 2.6203 . . no C11 H15D 2.8980 . 1_455 no C12 H13C 3.0856 . 1_455 no C12 H12B 2.9401 . 2_657 no C13 H12B 2.8308 . 2_657 no C13 H13A 2.5842 . . no C13 H12A 3.0772 . 1_655 no C13' H13D 2.5963 . . no C13' H12A 2.8902 . 1_655 no C14 H12A 2.9180 . 1_655 no C14' H12A 2.8353 . 1_655 no C15 H20 2.9643 . 2_666 no C15 H15B 2.5945 . . no C15 H16D 3.0988 . 1_655 no C15' H15C 2.6089 . . no C15' H16D 2.9832 . 1_655 no C16 H15D 3.0848 . 1_455 no C21 H61' 3.0925 . 1_455 no C22 H51' 3.0223 . 1_455 no H1 O11' 1.4824 . 1_465 no H1 S11' 2.5143 . 1_465 no H2A O1 2.3485 . . no H2B H3A 2.5651 . 2_666 no H3A H2B 2.5651 . 2_666 no H3A C3' 2.6106 . . no H3A H31' 1.9100 . . no H3B N1 2.9014 . 1_655 no H3B H5A 2.5751 . . no H3B O1 2.6339 . 1_655 no H3B C1 3.0085 . 1_655 no H5A H3B 2.5751 . . no H5A N1 2.8744 . 1_655 no H5B C5' 2.6203 . . no H5B H52' 1.9211 . . no H6B H15C 2.3861 . 2_666 no H11 O1' 1.7296 . 1_456 no H11 S1' 2.4711 . 1_456 no H12A C13 3.0772 . 1_455 no H12A C13' 2.8902 . 1_455 no H12A H13B 2.5494 . 1_455 no H12A C14' 2.8353 . 1_455 no H12A C14 2.9180 . 1_455 no H12B H13C 2.5716 . 2_657 no H12B H12B 2.2734 . 2_657 no H12B O11 2.2996 . . no H12B C13 2.8308 . 2_657 no H12B C12 2.9401 . 2_657 no H12C O11' 2.6547 . 1_455 no H13A O1' 2.8647 . 2_756 no H13A C13 2.5842 . . no H13A H13D 1.8962 . . no H13B O11' 2.6662 . . no H13B H12A 2.5494 . 1_655 no H13B H15A 2.5317 . . no H13C C12 3.0856 . 1_655 no H13C O11 2.7802 . 1_655 no H13C H12B 2.5716 . 2_657 no H13C H15D 2.5536 . . no H13D O11 2.5739 . 2_657 no H13D C13' 2.5963 . . no H13D H13A 1.8962 . . no H15A O11' 2.6954 . . no H15A H13B 2.5317 . . no H15B C15 2.5945 . . no H15B H15C 1.9077 . . no H15C H15B 1.9077 . . no H15C H6B 2.3861 . 2_666 no H15C C15' 2.6089 . . no H15D N11 2.7672 . 1_655 no H15D C16 3.0848 . 1_655 no H15D C11 2.8980 . 1_655 no H15D H20 2.4966 . 2_666 no H15D H13C 2.5536 . . no H16A O11' 2.4338 . 2_756 no H16B O11' 2.8903 . 1_455 no H16C H20 2.4913 . 2_666 no H16D C15' 2.9832 . 1_455 no H16D C15 3.0988 . 1_455 no H20 H15D 2.4966 . 2_666 no H20 C15 2.9643 . 2_666 no H20 H16C 2.4913 . 2_666 no H21 N11 2.6357 . 1_554 no H21' O1' 2.7529 . 1_455 no H22' O1 2.6876 . 2_666 no H31' H3A 1.9100 . . no H31' C3 2.5950 . . no H32' O1' 2.6783 . . no H32' H51' 2.5603 . . no H51' O1' 2.6711 . . no H51' C22 3.0223 . 1_655 no H51' H32' 2.5603 . . no H52' H5B 1.9211 . . no H52' C5 2.6052 . . no H61' C21 3.0925 . 1_655 no H62' O1' 2.6451 . 1_455 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 S11' 1.2397 2.5143 3.696(5) 158.54 1_465 yes O1 H1 O11' 1.2397 1.4824 2.706(6) 167.54 1_465 yes O11 H11 S1' 1.1218 2.4711 3.540(5) 158.65 1_456 yes O11 H11 O1' 1.1218 1.7296 2.729(6) 145.46 1_456 yes C2 H2A O1 0.9710 2.3485 2.715(11) 101.52 . yes C12 H12B O11 0.9702 2.2996 2.704(8) 104.02 . yes C13 H13D O11 0.9699 2.5739 3.406(8) 143.89 2_657 yes C16' H16A O11' 0.9705 2.4338 3.373(6) 162.65 2_756 yes _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 1.000 # End of Crystallographic Information File