# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Pantos, G.' _publ_contact_author_email gdp26@cam.ac.uk _publ_section_title ; The Sergeants-and-Soldiers Effect: Chiral Amplification in Naphthalenediimide Nanotubes ; loop_ _publ_author_name T.Anderson J.Sanders G.Pantos # Attachment '- 743751.txt' data_js0810 #TrackingRef '- 743751.txt' _database_code_depnum_ccdc_archive 'CCDC 743751' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 N2 O8, 3(C2 H6 O S)' _chemical_formula_sum 'C28 H32 N2 O11 S3' _chemical_formula_weight 668.74 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0612(2) _cell_length_b 11.8489(2) _cell_length_c 28.6964(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.513(1) _cell_angle_gamma 90.00 _cell_volume 3047.05(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20987 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; One of the DMSO molecules is disordered over two sites: a common isotropic displacement parameter was assigned to the C and O atoms of this moiety. The -COOH hydrogen atoms were NOT located but placed in chemically reasonable positions. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11900 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.81 _reflns_number_total 6197 _reflns_number_gt 5337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0906P)^2^+4.5561P] 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 6197 _refine_ls_number_parameters 406 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1676 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.058 _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 1.1028(2) 0.23610(15) 0.09713(6) 0.0251(4) Uani 1 1 d . . . N1 N 1.1721(2) 0.41871(17) 0.11319(7) 0.0173(4) Uani 1 1 d . . . C11 C 0.9592(3) 0.2902(2) 0.00520(8) 0.0188(5) Uani 1 1 d . . . H11 H 0.9581 0.2131 0.0143 0.023 Uiso 1 1 calc R . . O12 O 1.2862(2) 0.59034(16) 0.12219(6) 0.0260(4) Uani 1 1 d . . . C12 C 1.0325(3) 0.36878(19) 0.03589(8) 0.0165(5) Uani 1 1 d . . . C13 C 1.0368(3) 0.48301(19) 0.02235(7) 0.0147(4) Uani 1 1 d . . . C14 C 1.1136(3) 0.5645(2) 0.05267(8) 0.0168(5) Uani 1 1 d . . . C15 C 1.1136(3) 0.6766(2) 0.03930(8) 0.0202(5) Uani 1 1 d . . . H15 H 1.1630 0.7313 0.0603 0.024 Uiso 1 1 calc R . . C16 C 1.1026(3) 0.3336(2) 0.08357(8) 0.0184(5) Uani 1 1 d . . . C17 C 1.1986(3) 0.5285(2) 0.09855(8) 0.0182(5) Uani 1 1 d . . . O11' O 1.4281(2) 0.27232(17) 0.20202(6) 0.0264(4) Uani 1 1 d . . . H11' H 1.5078 0.2369 0.2008 0.032 Uiso 1 1 calc R . . C11' C 1.2379(3) 0.3826(2) 0.15985(8) 0.0191(5) Uani 1 1 d . . . O12' O 1.4428(2) 0.30820(18) 0.12605(7) 0.0304(4) Uani 1 1 d . . . C12' C 1.3804(3) 0.3177(2) 0.16038(9) 0.0212(5) Uani 1 1 d . . . C13' C 1.1323(3) 0.3513(2) 0.19386(9) 0.0264(6) Uani 1 1 d . . . H13A H 1.0239 0.3575 0.1827 0.032 Uiso 1 1 calc R . . H13B H 1.1613 0.2881 0.2159 0.032 Uiso 1 1 calc R . . C14' C 1.2202(3) 0.4580(2) 0.20112(9) 0.0263(6) Uani 1 1 d . . . H14A H 1.3034 0.4608 0.2277 0.032 Uiso 1 1 calc R . . H14B H 1.1660 0.5301 0.1944 0.032 Uiso 1 1 calc R . . C21 C 0.6345(3) 0.3223(2) 0.03013(9) 0.0206(5) Uani 1 1 d . . . H21 H 0.6905 0.2654 0.0482 0.025 Uiso 1 1 calc R . . N21 N 0.6645(2) 0.55678(18) 0.11666(7) 0.0184(4) Uani 1 1 d . . . O21 O 0.8050(2) 0.39760(16) 0.11585(6) 0.0261(4) Uani 1 1 d . . . C22 C 0.6227(3) 0.4283(2) 0.04900(8) 0.0165(5) Uani 1 1 d . . . O22 O 0.5724(2) 0.73596(16) 0.11031(6) 0.0255(4) Uani 1 1 d . . . C23 C 0.5353(3) 0.51209(19) 0.02317(8) 0.0159(4) Uani 1 1 d . . . C24 C 0.5174(3) 0.6200(2) 0.04235(8) 0.0174(5) Uani 1 1 d . . . C25 C 0.4357(3) 0.7020(2) 0.01570(9) 0.0207(5) Uani 1 1 d . . . H25 H 0.4270 0.7753 0.0285 0.025 Uiso 1 1 calc R . . C26 C 0.7053(3) 0.4567(2) 0.09610(8) 0.0189(5) Uani 1 1 d . . . C27 C 0.5840(3) 0.6452(2) 0.09165(8) 0.0186(5) Uani 1 1 d . . . C21' C 0.7326(3) 0.5822(2) 0.16430(8) 0.0211(5) Uani 1 1 d . . . O21' O 0.9315(2) 0.68696(19) 0.20736(7) 0.0343(5) Uani 1 1 d . . . C22' C 0.8689(3) 0.6544(2) 0.16916(9) 0.0238(5) Uani 1 1 d . . . O22' O 0.9128(2) 0.67886(18) 0.12852(7) 0.0287(4) Uani 1 1 d . . . H22' H 0.9895 0.7195 0.1333 0.034 Uiso 1 1 calc R . . C23' C 0.7244(3) 0.4937(3) 0.20170(9) 0.0290(6) Uani 1 1 d . . . H23A H 0.6745 0.4214 0.1918 0.035 Uiso 1 1 calc R . . H23B H 0.8102 0.4872 0.2273 0.035 Uiso 1 1 calc R . . C24' C 0.6293(3) 0.5970(3) 0.20070(9) 0.0297(6) Uani 1 1 d . . . H24A H 0.6564 0.6542 0.2256 0.036 Uiso 1 1 calc R . . H24B H 0.5208 0.5884 0.1902 0.036 Uiso 1 1 calc R . . S31 S 0.21330(9) 1.03464(6) 0.01016(3) 0.0340(2) Uani 1 1 d D . . O31 O 0.2553(3) 0.9214(2) -0.00570(14) 0.0731(11) Uani 1 1 d D . . C31 C 0.3789(5) 1.0887(4) 0.04414(15) 0.0631(12) Uani 1 1 d D . . H31B H 0.4020 1.0451 0.0733 0.095 Uiso 1 1 calc R . . H31C H 0.3638 1.1681 0.0518 0.095 Uiso 1 1 calc R . . H31D H 0.4620 1.0827 0.0260 0.095 Uiso 1 1 calc R . . C32 C 0.2156(5) 1.1254(4) -0.03980(14) 0.0531(10) Uani 1 1 d D . . H32A H 0.1281 1.1099 -0.0633 0.080 Uiso 1 1 calc R . . H32B H 0.3066 1.1116 -0.0536 0.080 Uiso 1 1 calc R . . H32C H 0.2135 1.2043 -0.0297 0.080 Uiso 1 1 calc R . . S41 S 0.68006(10) 1.07158(7) 0.15833(3) 0.0392(2) Uani 1 1 d . . . O41 O 0.6303(3) 1.1186(2) 0.20207(8) 0.0476(6) Uani 1 1 d . . . C41 C 0.8491(7) 1.1372(4) 0.1529(3) 0.120(3) Uani 1 1 d . . . H41B H 0.8297 1.2121 0.1389 0.180 Uiso 1 1 calc R . . H41C H 0.9037 1.0915 0.1326 0.180 Uiso 1 1 calc R . . H41D H 0.9090 1.1447 0.1841 0.180 Uiso 1 1 calc R . . C42 C 0.7532(4) 0.9360(3) 0.17389(13) 0.0426(8) Uani 1 1 d . . . H42A H 0.6731 0.8868 0.1815 0.064 Uiso 1 1 calc R . . H42B H 0.8309 0.9422 0.2014 0.064 Uiso 1 1 calc R . . H42C H 0.7961 0.9039 0.1474 0.064 Uiso 1 1 calc R . . S51 S 1.16632(11) 0.89789(8) 0.17680(3) 0.0274(2) Uani 0.70 1 d PD A 1 O51 O 1.0829(5) 0.8526(4) 0.13151(17) 0.0321(5) Uiso 0.70 1 d PD A 1 C51 C 1.2807(5) 1.0069(4) 0.15955(16) 0.0321(5) Uiso 0.70 1 d PD A 1 H51B H 1.2177 1.0677 0.1444 0.048 Uiso 0.70 1 calc PR A 1 H51C H 1.3431 0.9768 0.1374 0.048 Uiso 0.70 1 calc PR A 1 H51D H 1.3445 1.0367 0.1874 0.048 Uiso 0.70 1 calc PR A 1 C52 C 1.3165(5) 0.8021(4) 0.19647(18) 0.0321(5) Uiso 0.70 1 d PD A 1 H52A H 1.2770 0.7352 0.2105 0.048 Uiso 0.70 1 calc PR A 1 H52B H 1.3895 0.8395 0.2201 0.048 Uiso 0.70 1 calc PR A 1 H52C H 1.3650 0.7794 0.1696 0.048 Uiso 0.70 1 calc PR A 1 S61 S 1.2523(3) 0.8859(2) 0.14525(8) 0.0262(5) Uani 0.30 1 d PD B 2 O61 O 1.1004(10) 0.8464(10) 0.1271(4) 0.0321(5) Uiso 0.30 1 d PD B 2 C61 C 1.2355(13) 1.0232(7) 0.1720(4) 0.0321(5) Uiso 0.30 1 d PD B 2 H61B H 1.2322 1.0820 0.1478 0.048 Uiso 0.30 1 calc PR B 2 H61C H 1.3215 1.0360 0.1964 0.048 Uiso 0.30 1 calc PR B 2 H61D H 1.1436 1.0258 0.1862 0.048 Uiso 0.30 1 calc PR B 2 C62 C 1.2805(13) 0.8011(10) 0.2017(4) 0.0321(5) Uiso 0.30 1 d PD B 2 H62A H 1.3010 0.7222 0.1946 0.048 Uiso 0.30 1 calc PR B 2 H62B H 1.1901 0.8050 0.2167 0.048 Uiso 0.30 1 calc PR B 2 H62C H 1.3650 0.8320 0.2232 0.048 Uiso 0.30 1 calc PR B 2 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 0.0320(11) 0.0186(9) 0.0224(9) 0.0064(7) -0.0031(8) -0.0004(7) N1 0.0185(10) 0.0190(10) 0.0130(9) 0.0032(7) -0.0020(8) 0.0001(8) C11 0.0216(12) 0.0160(11) 0.0181(11) 0.0019(8) 0.0002(9) -0.0006(9) O12 0.0291(10) 0.0264(10) 0.0197(8) 0.0005(7) -0.0060(8) -0.0078(8) C12 0.0170(11) 0.0171(11) 0.0149(10) 0.0016(8) 0.0002(9) 0.0011(8) C13 0.0139(11) 0.0169(11) 0.0132(10) 0.0007(8) 0.0015(9) 0.0010(8) C14 0.0186(11) 0.0166(11) 0.0142(10) 0.0014(8) -0.0005(9) -0.0004(9) C15 0.0241(13) 0.0166(11) 0.0184(11) -0.0009(8) -0.0017(10) -0.0020(9) C16 0.0196(12) 0.0186(11) 0.0164(10) 0.0024(8) 0.0003(9) 0.0010(9) C17 0.0182(12) 0.0207(12) 0.0150(10) 0.0016(8) -0.0001(9) -0.0002(9) O11' 0.0249(10) 0.0327(10) 0.0200(9) 0.0058(7) -0.0025(8) 0.0082(8) C11' 0.0209(12) 0.0246(12) 0.0113(10) 0.0035(8) 0.0003(9) 0.0011(9) O12' 0.0266(10) 0.0417(12) 0.0235(9) 0.0054(8) 0.0057(8) 0.0066(8) C12' 0.0205(12) 0.0225(12) 0.0189(11) 0.0021(9) -0.0030(10) -0.0031(10) C13' 0.0238(13) 0.0365(15) 0.0187(11) 0.0072(10) 0.0020(10) 0.0020(11) C14' 0.0330(15) 0.0296(14) 0.0156(11) -0.0010(9) 0.0018(11) 0.0025(11) C21 0.0231(12) 0.0179(12) 0.0196(11) 0.0022(9) -0.0005(10) 0.0028(9) N21 0.0179(10) 0.0217(10) 0.0144(9) -0.0031(7) -0.0013(8) -0.0005(8) O21 0.0254(10) 0.0296(10) 0.0207(9) -0.0005(7) -0.0057(8) 0.0068(8) C22 0.0168(11) 0.0169(11) 0.0155(10) -0.0009(8) 0.0008(9) 0.0010(9) O22 0.0288(10) 0.0220(9) 0.0241(9) -0.0079(7) -0.0009(8) 0.0005(7) C23 0.0157(11) 0.0162(11) 0.0157(11) -0.0012(8) 0.0020(9) -0.0004(8) C24 0.0170(11) 0.0183(11) 0.0163(10) -0.0023(8) 0.0003(9) -0.0010(9) C25 0.0239(13) 0.0153(11) 0.0217(11) -0.0027(9) 0.0000(10) 0.0013(9) C26 0.0187(12) 0.0215(12) 0.0162(10) -0.0007(8) 0.0021(9) -0.0012(9) C27 0.0180(11) 0.0200(11) 0.0174(10) -0.0025(8) 0.0011(9) -0.0022(9) C21' 0.0229(12) 0.0262(13) 0.0135(10) -0.0025(9) 0.0004(10) 0.0013(10) O21' 0.0331(12) 0.0446(12) 0.0224(9) -0.0092(8) -0.0050(9) -0.0092(9) C22' 0.0203(12) 0.0280(13) 0.0217(12) -0.0055(10) -0.0020(10) 0.0026(10) O22' 0.0248(10) 0.0391(11) 0.0225(9) -0.0060(8) 0.0044(8) -0.0116(8) C23' 0.0334(15) 0.0368(15) 0.0159(11) 0.0032(10) 0.0005(11) -0.0028(12) C24' 0.0286(14) 0.0413(16) 0.0197(12) -0.0046(11) 0.0049(11) -0.0016(12) S31 0.0322(4) 0.0252(4) 0.0441(4) 0.0023(3) 0.0034(3) -0.0001(3) O31 0.0470(17) 0.0201(12) 0.151(4) -0.0059(15) 0.012(2) 0.0015(11) C31 0.051(2) 0.094(3) 0.045(2) -0.019(2) 0.0100(19) -0.022(2) C32 0.053(2) 0.059(2) 0.047(2) 0.0132(17) 0.0081(18) 0.0129(19) S41 0.0381(4) 0.0438(5) 0.0348(4) 0.0048(3) 0.0024(3) 0.0085(3) O41 0.0551(16) 0.0535(15) 0.0332(12) 0.0036(10) 0.0034(11) 0.0282(12) C41 0.084(4) 0.046(3) 0.244(9) 0.054(4) 0.072(5) -0.005(3) C42 0.059(2) 0.0288(16) 0.0416(17) -0.0053(13) 0.0121(17) 0.0009(15) S51 0.0269(5) 0.0273(5) 0.0265(5) -0.0039(4) -0.0004(4) -0.0039(4) S61 0.0251(11) 0.0313(11) 0.0216(9) -0.0031(8) 0.0014(9) -0.0023(9) _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 C16 1.218(3) . ? N1 C17 1.399(3) . ? N1 C16 1.406(3) . ? N1 C11' 1.447(3) . ? C11 C12 1.382(3) . ? C11 C15 1.405(3) 3_765 ? C11 H11 0.9500 . ? O12 C17 1.212(3) . ? C12 C13 1.410(3) . ? C12 C16 1.481(3) . ? C13 C14 1.413(3) . ? C13 C13 1.414(4) 3_765 ? C14 C15 1.382(3) . ? C14 C17 1.486(3) . ? C15 C11 1.405(3) 3_765 ? C15 H15 0.9500 . ? O11' C12' 1.323(3) . ? O11' H11' 0.8400 . ? C11' C12' 1.501(4) . ? C11' C13' 1.511(4) . ? C11' C14' 1.511(3) . ? O12' C12' 1.212(3) . ? C13' C14' 1.492(4) . ? C13' H13A 0.9900 . ? C13' H13B 0.9900 . ? C14' H14A 0.9900 . ? C14' H14B 0.9900 . ? C21 C22 1.379(3) . ? C21 C25 1.403(3) 3_665 ? C21 H21 0.9500 . ? N21 C26 1.398(3) . ? N21 C27 1.411(3) . ? N21 C21' 1.446(3) . ? O21 C26 1.215(3) . ? C22 C23 1.410(3) . ? C22 C26 1.483(3) . ? O22 C27 1.213(3) . ? C23 C24 1.411(3) . ? C23 C23 1.417(4) 3_665 ? C24 C25 1.382(3) . ? C24 C27 1.484(3) . ? C25 C21 1.403(3) 3_665 ? C25 H25 0.9500 . ? C21' C22' 1.492(4) . ? C21' C23' 1.510(4) . ? C21' C24' 1.513(4) . ? O21' C22' 1.220(3) . ? C22' O22' 1.319(3) . ? O22' H22' 0.8400 . ? C23' C24' 1.495(4) . ? C23' H23A 0.9900 . ? C23' H23B 0.9900 . ? C24' H24A 0.9900 . ? C24' H24B 0.9900 . ? S31 O31 1.485(3) . ? S31 C31 1.783(4) . ? S31 C32 1.795(4) . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C31 H31D 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? S41 O41 1.502(3) . ? S41 C41 1.745(5) . ? S41 C42 1.770(3) . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C41 H41D 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? S51 O51 1.502(5) . ? S51 C51 1.772(4) . ? S51 C52 1.798(5) . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C51 H51D 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? S61 O61 1.474(9) . ? S61 C61 1.815(9) . ? S61 C62 1.892(10) . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? C61 H61D 0.9800 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 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 C17 N1 C16 124.55(19) . . ? C17 N1 C11' 119.2(2) . . ? C16 N1 C11' 115.65(19) . . ? C12 C11 C15 120.4(2) . 3_765 ? C12 C11 H11 119.8 . . ? C15 C11 H11 119.8 3_765 . ? C11 C12 C13 120.1(2) . . ? C11 C12 C16 119.9(2) . . ? C13 C12 C16 120.0(2) . . ? C12 C13 C14 121.2(2) . . ? C12 C13 C13 119.7(3) . 3_765 ? C14 C13 C13 119.2(3) . 3_765 ? C15 C14 C13 120.4(2) . . ? C15 C14 C17 120.0(2) . . ? C13 C14 C17 119.5(2) . . ? C14 C15 C11 120.2(2) . 3_765 ? C14 C15 H15 119.9 . . ? C11 C15 H15 119.9 3_765 . ? O1 C16 N1 120.5(2) . . ? O1 C16 C12 122.8(2) . . ? N1 C16 C12 116.6(2) . . ? O12 C17 N1 121.5(2) . . ? O12 C17 C14 122.2(2) . . ? N1 C17 C14 116.3(2) . . ? C12' O11' H11' 109.5 . . ? N1 C11' C12' 113.4(2) . . ? N1 C11' C13' 117.2(2) . . ? C12' C11' C13' 119.6(2) . . ? N1 C11' C14' 118.2(2) . . ? C12' C11' C14' 119.1(2) . . ? C13' C11' C14' 59.20(18) . . ? O12' C12' O11' 124.6(2) . . ? O12' C12' C11' 122.9(2) . . ? O11' C12' C11' 112.5(2) . . ? C14' C13' C11' 60.42(17) . . ? C14' C13' H13A 117.7 . . ? C11' C13' H13A 117.7 . . ? C14' C13' H13B 117.7 . . ? C11' C13' H13B 117.7 . . ? H13A C13' H13B 114.9 . . ? C13' C14' C11' 60.38(17) . . ? C13' C14' H14A 117.7 . . ? C11' C14' H14A 117.7 . . ? C13' C14' H14B 117.7 . . ? C11' C14' H14B 117.7 . . ? H14A C14' H14B 114.9 . . ? C22 C21 C25 120.3(2) . 3_665 ? C22 C21 H21 119.9 . . ? C25 C21 H21 119.9 3_665 . ? C26 N21 C27 124.3(2) . . ? C26 N21 C21' 118.2(2) . . ? C27 N21 C21' 116.3(2) . . ? C21 C22 C23 120.4(2) . . ? C21 C22 C26 120.4(2) . . ? C23 C22 C26 119.2(2) . . ? C22 C23 C24 121.4(2) . . ? C22 C23 C23 119.5(3) . 3_665 ? C24 C23 C23 119.1(3) . 3_665 ? C25 C24 C23 120.3(2) . . ? C25 C24 C27 119.7(2) . . ? C23 C24 C27 120.0(2) . . ? C24 C25 C21 120.4(2) . 3_665 ? C24 C25 H25 119.8 . . ? C21 C25 H25 119.8 3_665 . ? O21 C26 N21 121.1(2) . . ? O21 C26 C22 122.3(2) . . ? N21 C26 C22 116.6(2) . . ? O22 C27 N21 120.4(2) . . ? O22 C27 C24 123.3(2) . . ? N21 C27 C24 116.3(2) . . ? N21 C21' C22' 116.1(2) . . ? N21 C21' C23' 117.9(2) . . ? C22' C21' C23' 117.3(2) . . ? N21 C21' C24' 117.1(2) . . ? C22' C21' C24' 117.2(2) . . ? C23' C21' C24' 59.28(19) . . ? O21' C22' O22' 124.4(3) . . ? O21' C22' C21' 122.2(3) . . ? O22' C22' C21' 113.4(2) . . ? C22' O22' H22' 109.5 . . ? C24' C23' C21' 60.46(18) . . ? C24' C23' H23A 117.7 . . ? C21' C23' H23A 117.7 . . ? C24' C23' H23B 117.7 . . ? C21' C23' H23B 117.7 . . ? H23A C23' H23B 114.8 . . ? C23' C24' C21' 60.26(18) . . ? C23' C24' H24A 117.7 . . ? C21' C24' H24A 117.7 . . ? C23' C24' H24B 117.7 . . ? C21' C24' H24B 117.7 . . ? H24A C24' H24B 114.9 . . ? O31 S31 C31 105.0(2) . . ? O31 S31 C32 105.2(2) . . ? C31 S31 C32 96.5(2) . . ? S31 C31 H31B 109.5 . . ? S31 C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? S31 C31 H31D 109.5 . . ? H31B C31 H31D 109.5 . . ? H31C C31 H31D 109.5 . . ? S31 C32 H32A 109.5 . . ? S31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? S31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O41 S41 C41 106.6(3) . . ? O41 S41 C42 105.84(15) . . ? C41 S41 C42 97.2(2) . . ? S41 C41 H41B 109.5 . . ? S41 C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? S41 C41 H41D 109.5 . . ? H41B C41 H41D 109.5 . . ? H41C C41 H41D 109.5 . . ? S41 C42 H42A 109.5 . . ? S41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? S41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O51 S51 C51 105.0(3) . . ? O51 S51 C52 107.9(3) . . ? C51 S51 C52 95.8(2) . . ? O61 S61 C61 107.5(6) . . ? O61 S61 C62 97.8(6) . . ? C61 S61 C62 97.1(5) . . ? S61 C61 H61B 109.5 . . ? S61 C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? S61 C61 H61D 109.5 . . ? H61B C61 H61D 109.5 . . ? H61C C61 H61D 109.5 . . ? S61 C62 H62A 109.5 . . ? S61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? S61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C11 C12 C13 -1.1(4) 3_765 . . . ? C15 C11 C12 C16 177.0(2) 3_765 . . . ? C11 C12 C13 C14 -178.6(2) . . . . ? C16 C12 C13 C14 3.2(3) . . . . ? C11 C12 C13 C13 1.3(4) . . . 3_765 ? C16 C12 C13 C13 -176.8(3) . . . 3_765 ? C12 C13 C14 C15 -178.4(2) . . . . ? C13 C13 C14 C15 1.7(4) 3_765 . . . ? C12 C13 C14 C17 3.5(3) . . . . ? C13 C13 C14 C17 -176.5(3) 3_765 . . . ? C13 C14 C15 C11 -1.9(4) . . . 3_765 ? C17 C14 C15 C11 176.2(2) . . . 3_765 ? C17 N1 C16 O1 169.3(2) . . . . ? C11' N1 C16 O1 -1.5(3) . . . . ? C17 N1 C16 C12 -10.1(3) . . . . ? C11' N1 C16 C12 179.1(2) . . . . ? C11 C12 C16 O1 2.1(4) . . . . ? C13 C12 C16 O1 -179.8(2) . . . . ? C11 C12 C16 N1 -178.5(2) . . . . ? C13 C12 C16 N1 -0.4(3) . . . . ? C16 N1 C17 O12 -163.5(2) . . . . ? C11' N1 C17 O12 7.0(4) . . . . ? C16 N1 C17 C14 16.5(3) . . . . ? C11' N1 C17 C14 -173.0(2) . . . . ? C15 C14 C17 O12 -10.9(4) . . . . ? C13 C14 C17 O12 167.3(2) . . . . ? C15 C14 C17 N1 169.1(2) . . . . ? C13 C14 C17 N1 -12.8(3) . . . . ? C17 N1 C11' C12' -97.2(3) . . . . ? C16 N1 C11' C12' 74.2(3) . . . . ? C17 N1 C11' C13' 117.0(3) . . . . ? C16 N1 C11' C13' -71.6(3) . . . . ? C17 N1 C11' C14' 49.2(3) . . . . ? C16 N1 C11' C14' -139.4(2) . . . . ? N1 C11' C12' O12' 8.2(4) . . . . ? C13' C11' C12' O12' 153.1(3) . . . . ? C14' C11' C12' O12' -137.9(3) . . . . ? N1 C11' C12' O11' -171.4(2) . . . . ? C13' C11' C12' O11' -26.5(3) . . . . ? C14' C11' C12' O11' 42.5(3) . . . . ? N1 C11' C13' C14' -108.2(2) . . . . ? C12' C11' C13' C14' 108.2(3) . . . . ? N1 C11' C14' C13' 106.5(3) . . . . ? C12' C11' C14' C13' -109.0(3) . . . . ? C25 C21 C22 C23 2.4(4) 3_665 . . . ? C25 C21 C22 C26 -175.7(2) 3_665 . . . ? C21 C22 C23 C24 177.8(2) . . . . ? C26 C22 C23 C24 -4.0(4) . . . . ? C21 C22 C23 C23 -2.6(4) . . . 3_665 ? C26 C22 C23 C23 175.6(3) . . . 3_665 ? C22 C23 C24 C25 177.6(2) . . . . ? C23 C23 C24 C25 -2.0(4) 3_665 . . . ? C22 C23 C24 C27 -3.5(4) . . . . ? C23 C23 C24 C27 176.9(3) 3_665 . . . ? C23 C24 C25 C21 2.2(4) . . . 3_665 ? C27 C24 C25 C21 -176.7(2) . . . 3_665 ? C27 N21 C26 O21 160.6(2) . . . . ? C21' N21 C26 O21 -6.7(4) . . . . ? C27 N21 C26 C22 -18.4(3) . . . . ? C21' N21 C26 C22 174.4(2) . . . . ? C21 C22 C26 O21 13.6(4) . . . . ? C23 C22 C26 O21 -164.6(2) . . . . ? C21 C22 C26 N21 -167.5(2) . . . . ? C23 C22 C26 N21 14.4(3) . . . . ? C26 N21 C27 O22 -168.7(2) . . . . ? C21' N21 C27 O22 -1.2(3) . . . . ? C26 N21 C27 C24 11.0(3) . . . . ? C21' N21 C27 C24 178.5(2) . . . . ? C25 C24 C27 O22 -0.9(4) . . . . ? C23 C24 C27 O22 -179.8(2) . . . . ? C25 C24 C27 N21 179.4(2) . . . . ? C23 C24 C27 N21 0.5(3) . . . . ? C26 N21 C21' C22' 93.7(3) . . . . ? C27 N21 C21' C22' -74.5(3) . . . . ? C26 N21 C21' C23' -53.2(3) . . . . ? C27 N21 C21' C23' 138.5(2) . . . . ? C26 N21 C21' C24' -121.0(3) . . . . ? C27 N21 C21' C24' 70.7(3) . . . . ? N21 C21' C22' O21' 175.8(3) . . . . ? C23' C21' C22' O21' -37.1(4) . . . . ? C24' C21' C22' O21' 30.5(4) . . . . ? N21 C21' C22' O22' -4.1(3) . . . . ? C23' C21' C22' O22' 143.1(2) . . . . ? C24' C21' C22' O22' -149.3(2) . . . . ? N21 C21' C23' C24' -106.5(3) . . . . ? C22' C21' C23' C24' 106.9(3) . . . . ? N21 C21' C24' C23' 107.9(3) . . . . ? C22' C21' C24' C23' -107.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.859 _refine_diff_density_max 0.956 _refine_diff_density_min -0.762 _refine_diff_density_rms 0.078