# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Jonathan L Sessler' _publ_contact_author_address ; Department of Chemistry and Biochemistry and Institute for Cellular and Molecula The University of Texas at Austin 1 University Station-A5300, The Un Austin Texas 78712-0165 USA ; _publ_contact_author_email sessler@mail.utexas.edu _publ_section_title ; Straightforward synthesis of sulfur bridged oligopyrrolic macrocycles ; loop_ _publ_author_name 'Jonathan L. Sessler' 'Thomas Kohler' 'Vincent Lynch' 'David Sanchez-Garcia' 'Daniel Seidel' data_5a _database_code_depnum_ccdc_archive 'CCDC 260321' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H60 N4 O4 S8' _chemical_formula_weight 869.36 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.9670(3) _cell_length_b 19.1060(5) _cell_length_c 16.5190(4) _cell_angle_alpha 90.00 _cell_angle_beta 119.0531(11) _cell_angle_gamma 90.00 _cell_volume 4405.27(18) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17029 _diffrn_reflns_av_R_equivalents 0.0701 _diffrn_reflns_av_sigmaI/netI 0.1438 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.49 _reflns_number_total 9859 _reflns_number_gt 5809 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. There appeared to be four molecules of DMSO per asymmetric unit. Two molecules were H-bound to the macrocycle by way of the oxygen atom of the DMSO molecule and the pyrrole NH moieties. Both molecules of DMSO were disordered. These DMSO were disordered by inversion of the pyramidal molecule in such a way that the methyl carbon atom and the oygen atom positions were nearly unchanged in the two orientations. The disorder was modeled in the same fashion for both molecules. The geometry of the DMSO molecules was restrained to be equivalent throughout the refinement process. The site occupancy factor of the sulfur atom of the primary component of the disorder was assigned the variable x. The site occupancy of the minor component of the disordered DMSO molecule was assigned (1-x). A common isotropic displacement parameter was refined for both S atoms. The resulting site occupancy factors were assigned on the basis of this refinement. The site occupancy factor for the major component of the DMSO molecule, S1a, C1a, C2a and O1a refined to 90(2)%. Subsequent refinement of the disorder of this molecule revealed that the disordered involved only the sulfur atom and one methyl group. Therefore, the site occupancy factor for O1a and C1a were set to 100%. The second H-bound DMSO molecule was also disordered. The site occupancy factors for the two components of the disorder was determined as described for the first molecule. The site occupancy factor for the major component of the disorder refined to 92(2)%. For this molecule, it appeared that the sulfur atom and the two methyl groups were involved in the disorder so that the site occupancy for the oxygen atom, O1B, was reset to full occupancy in the final refinement model. In addition to the H-bound DMSO molecules, there appeared to be two other molecules of DMSO in the asymmetric unit. These molecules were located in a channel located along x, 1/2, 1/2. The molecules were badly disordered and could not be modeled satisfactorily. Therefore, the contribution to the scattering due to the electron density in this channel was removed by use of the utility SQUEEZE (Sluis and Spek, 1990) in PLATON98 (Spek, 1998). PLATON98 was used as incorporated in WinGX (Farrugia, 1999). ; _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^)+(0.0423P)^2^+5.1948P] 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 9859 _refine_ls_number_parameters 414 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.1770 _refine_ls_R_factor_gt 0.1004 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_restrained_S_all 1.293 _refine_ls_shift/su_max 0.416 _refine_ls_shift/su_mean 0.005 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 0.1556(2) 0.28314(18) 0.2718(2) 0.0210(8) Uani 1 1 d . . . H1N H 0.1237 0.3022 0.2970 0.025 Uiso 1 1 d R . . N2 N 0.0406(2) 0.16739(19) 0.2909(2) 0.0242(9) Uani 1 1 d . . . H2N H -0.0012 0.1978 0.2524 0.029 Uiso 1 1 d R . . N3 N -0.0964(3) 0.30045(18) 0.3111(2) 0.0234(8) Uani 1 1 d . . . H3N H -0.0348 0.2953 0.3305 0.028 Uiso 1 1 d R . . N4 N -0.0545(2) 0.37881(18) 0.1805(2) 0.0207(8) Uani 1 1 d . . . H4N H -0.0384 0.3351 0.1783 0.025 Uiso 1 1 d R . . C1 C 0.1974(3) 0.3191(2) 0.2274(3) 0.0249(10) Uani 1 1 d . . . C2 C 0.2421(3) 0.2702(2) 0.1999(3) 0.0262(11) Uani 1 1 d . . . C3 C 0.2275(3) 0.2036(2) 0.2272(3) 0.0250(10) Uani 1 1 d . . . C4 C 0.1738(3) 0.2131(2) 0.2714(3) 0.0225(10) Uani 1 1 d . . . C5 C 0.1342(3) 0.1623(2) 0.3111(3) 0.0211(10) Uani 1 1 d . . . C6 C 0.1758(3) 0.1082(2) 0.3728(3) 0.0249(10) Uani 1 1 d . . . C7 C 0.1053(3) 0.0798(2) 0.3917(3) 0.0267(11) Uani 1 1 d . . . C8 C 0.0222(3) 0.1172(2) 0.3388(3) 0.0257(11) Uani 1 1 d . . . S9 S -0.09072(9) 0.10644(7) 0.32922(9) 0.0350(3) Uani 1 1 d . . . S10 S -0.10132(9) 0.18717(7) 0.41043(9) 0.0353(3) Uani 1 1 d . . . C11 C -0.1513(3) 0.2572(2) 0.3339(3) 0.0274(11) Uani 1 1 d . . . C12 C -0.2444(3) 0.2813(2) 0.2891(3) 0.0271(11) Uani 1 1 d . . . C13 C -0.2455(3) 0.3423(2) 0.2396(3) 0.0266(11) Uani 1 1 d . . . C14 C -0.1531(3) 0.3515(2) 0.2537(3) 0.0216(10) Uani 1 1 d . . . C15 C -0.1135(3) 0.4018(2) 0.2139(3) 0.0226(10) Uani 1 1 d . . . C16 C -0.1189(3) 0.4741(2) 0.2074(3) 0.0217(10) Uani 1 1 d . . . C17 C -0.0620(3) 0.4961(2) 0.1668(3) 0.0212(10) Uani 1 1 d . . . C18 C -0.0225(3) 0.4359(2) 0.1529(3) 0.0205(10) Uani 1 1 d . . . S19 S 0.05112(8) 0.42773(6) 0.10270(8) 0.0242(3) Uani 1 1 d . . . S20 S 0.18909(8) 0.40946(6) 0.21513(8) 0.0268(3) Uani 1 1 d . . . C21 C 0.2931(3) 0.2855(3) 0.1451(3) 0.0349(12) Uani 1 1 d . . . H21A H 0.2756 0.3315 0.1186 0.042 Uiso 1 1 d R . . H21B H 0.2725 0.2524 0.0954 0.042 Uiso 1 1 d R . . C22 C 0.4028(4) 0.2817(3) 0.2050(4) 0.0552(17) Uani 1 1 d . . . H22A H 0.4332 0.2915 0.1684 0.083 Uiso 1 1 d R . . H22B H 0.4234 0.3153 0.2542 0.083 Uiso 1 1 d R . . H22C H 0.4203 0.2355 0.2308 0.083 Uiso 1 1 d R . . C23 C 0.2561(4) 0.1347(3) 0.2037(4) 0.0374(13) Uani 1 1 d . . . H23C H 0.2484 0.0980 0.2393 0.056 Uiso 1 1 d R . . H23A H 0.3217 0.1364 0.2170 0.056 Uiso 1 1 d R . . H23B H 0.2166 0.1251 0.1389 0.056 Uiso 1 1 d R . . C24 C 0.2802(3) 0.0873(3) 0.4184(3) 0.0383(13) Uani 1 1 d . . . H24A H 0.3119 0.1144 0.3924 0.057 Uiso 1 1 d R . . H24B H 0.3094 0.0961 0.4837 0.057 Uiso 1 1 d R . . H24C H 0.2857 0.0384 0.4082 0.057 Uiso 1 1 d R . . C25 C 0.1187(4) 0.0195(2) 0.4553(3) 0.0354(12) Uani 1 1 d . . . H25A H 0.0744 0.0242 0.4787 0.042 Uiso 1 1 d R . . H25B H 0.1825 0.0210 0.5067 0.042 Uiso 1 1 d R . . C26 C 0.1036(4) -0.0511(3) 0.4073(4) 0.0432(14) Uani 1 1 d . . . H26A H 0.1125 -0.0890 0.4489 0.065 Uiso 1 1 d R . . H26B H 0.0395 -0.0523 0.3562 0.065 Uiso 1 1 d R . . H26C H 0.1484 -0.0556 0.3845 0.065 Uiso 1 1 d R . . C27 C -0.3277(3) 0.2484(3) 0.2946(3) 0.0355(12) Uani 1 1 d . . . H27A H -0.3165 0.1992 0.3071 0.043 Uiso 1 1 d R . . H27B H -0.3841 0.2541 0.2355 0.043 Uiso 1 1 d R . . C28 C -0.3462(4) 0.2818(3) 0.3673(4) 0.0514(16) Uani 1 1 d . . . H28A H -0.4001 0.2610 0.3690 0.077 Uiso 1 1 d R . . H28B H -0.2897 0.2756 0.4262 0.077 Uiso 1 1 d R . . H28C H -0.3578 0.3309 0.3541 0.077 Uiso 1 1 d R . . C29 C -0.3327(3) 0.3845(3) 0.1779(4) 0.0399(13) Uani 1 1 d . . . H29C H -0.3895 0.3578 0.1623 0.060 Uiso 1 1 d R . . H29A H -0.3310 0.3974 0.1225 0.060 Uiso 1 1 d R . . H29B H -0.3328 0.4267 0.2094 0.060 Uiso 1 1 d R . . C30 C -0.1702(4) 0.5213(3) 0.2413(3) 0.0354(12) Uani 1 1 d . . . H30A H -0.2373 0.5223 0.1971 0.053 Uiso 1 1 d R . . H30B H -0.1442 0.5677 0.2502 0.053 Uiso 1 1 d R . . H30C H -0.1612 0.5046 0.2998 0.053 Uiso 1 1 d R . . C31 C -0.0473(3) 0.5697(2) 0.1461(3) 0.0284(11) Uani 1 1 d . . . H31A H 0.0062 0.5715 0.1348 0.034 Uiso 1 1 d R . . H31B H -0.0328 0.5984 0.1990 0.034 Uiso 1 1 d R . . C32 C -0.1359(3) 0.5993(2) 0.0610(3) 0.0314(11) Uani 1 1 d . . . H32A H -0.1247 0.6467 0.0494 0.047 Uiso 1 1 d R . . H32B H -0.1498 0.5709 0.0080 0.047 Uiso 1 1 d R . . H32C H -0.1892 0.5980 0.0727 0.047 Uiso 1 1 d R . . S1A S 0.17677(11) 0.32533(8) 0.50727(9) 0.0339(4) Uani 0.90 1 d PD A 1 O1A O 0.1029(2) 0.32886(17) 0.40655(19) 0.0330(8) Uani 1 1 d D A 1 C1A C 0.2053(4) 0.2346(3) 0.5319(3) 0.0440(14) Uani 1 1 d D A 1 H1AA H 0.2421 0.2191 0.5035 0.066 Uiso 1 1 d R A 1 H1AB H 0.2417 0.2278 0.5977 0.066 Uiso 1 1 d R A 1 H1AC H 0.1470 0.2080 0.5076 0.066 Uiso 1 1 d R A 1 C2A C 0.1111(5) 0.3351(4) 0.5691(4) 0.059(2) Uani 0.90 1 d PD A 1 H2AA H 0.0893 0.3826 0.5638 0.088 Uiso 0.90 1 d PR A 1 H2AB H 0.0570 0.3041 0.5432 0.088 Uiso 0.90 1 d PR A 1 H2AC H 0.1517 0.3238 0.6332 0.088 Uiso 0.90 1 d PR A 1 S1AA S 0.1262(13) 0.3032(9) 0.5043(7) 0.061(5) Uiso 0.10 1 d PGD B 2 C2AA C 0.222(3) 0.357(3) 0.5812(10) 0.08(2) Uiso 0.10 1 d PGD B 2 H2AD H 0.2622 0.3319 0.6368 0.119 Uiso 0.10 1 d PR B 2 H2AE H 0.2585 0.3720 0.5523 0.119 Uiso 0.10 1 d PR B 2 H2AF H 0.1965 0.3979 0.5964 0.119 Uiso 0.10 1 d PR B 2 S1B S -0.03126(9) 0.18764(7) 0.05986(9) 0.0301(3) Uani 0.92 1 d PD C 1 O1B O -0.0690(2) 0.23511(16) 0.1097(2) 0.0301(8) Uani 1 1 d D C 1 C1B C 0.0162(5) 0.2424(3) 0.0070(4) 0.0474(16) Uani 0.92 1 d PD C 1 H1BA H 0.0743 0.2633 0.0537 0.071 Uiso 0.92 1 d PR C 1 H1BB H 0.0297 0.2152 -0.0343 0.071 Uiso 0.92 1 d PR C 1 H1BC H -0.0292 0.2784 -0.0273 0.071 Uiso 0.92 1 d PR C 1 C2B C -0.1330(4) 0.1602(4) -0.0441(4) 0.0584(19) Uani 0.92 1 d PD C 1 H2BA H -0.1705 0.1285 -0.0297 0.088 Uiso 0.92 1 d PR C 1 H2BB H -0.1712 0.2002 -0.0760 0.088 Uiso 0.92 1 d PR C 1 H2BC H -0.1123 0.1371 -0.0830 0.088 Uiso 0.92 1 d PR C 1 S1BB S -0.1109(11) 0.2149(8) 0.0091(6) 0.038(4) Uiso 0.08 1 d PGD D 2 C1BA C -0.034(3) 0.246(3) -0.031(2) 0.06(3) Uiso 0.08 1 d PGD D 2 H1BD H -0.0383 0.2963 -0.0349 0.090 Uiso 0.08 1 d PR D 2 H1BE H 0.0303 0.2325 0.0116 0.090 Uiso 0.08 1 d PR D 2 H1BF H -0.0531 0.2269 -0.0908 0.090 Uiso 0.08 1 d PR D 2 C2BA C -0.083(4) 0.1253(11) 0.0069(19) 0.06(2) Uiso 0.08 1 d PGD D 2 H2BD H -0.1196 0.0974 0.0273 0.086 Uiso 0.08 1 d PR D 2 H2BE H -0.0997 0.1122 -0.0551 0.086 Uiso 0.08 1 d PR D 2 H2BF H -0.0163 0.1178 0.0473 0.086 Uiso 0.08 1 d PR D 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 N1 0.0200(19) 0.023(2) 0.022(2) 0.0047(17) 0.0119(17) 0.0045(16) N2 0.021(2) 0.023(2) 0.028(2) 0.0068(17) 0.0111(17) 0.0054(16) N3 0.023(2) 0.025(2) 0.027(2) 0.0062(18) 0.0157(18) 0.0059(17) N4 0.0226(19) 0.019(2) 0.0216(19) 0.0037(17) 0.0119(17) 0.0068(16) C1 0.020(2) 0.030(3) 0.024(2) 0.007(2) 0.010(2) 0.002(2) C2 0.021(2) 0.034(3) 0.024(2) 0.007(2) 0.011(2) 0.007(2) C3 0.021(2) 0.029(3) 0.027(3) 0.007(2) 0.013(2) 0.007(2) C4 0.017(2) 0.024(3) 0.025(2) 0.000(2) 0.008(2) 0.002(2) C5 0.020(2) 0.024(2) 0.021(2) 0.000(2) 0.010(2) 0.001(2) C6 0.026(2) 0.024(3) 0.024(2) 0.001(2) 0.012(2) 0.002(2) C7 0.034(3) 0.026(3) 0.023(2) 0.002(2) 0.016(2) 0.002(2) C8 0.027(3) 0.025(3) 0.029(3) 0.004(2) 0.017(2) 0.003(2) S9 0.0320(7) 0.0282(7) 0.0534(8) 0.0059(6) 0.0274(7) 0.0005(6) S10 0.0430(8) 0.0351(8) 0.0408(8) 0.0161(6) 0.0306(7) 0.0133(6) C11 0.035(3) 0.030(3) 0.029(3) 0.014(2) 0.024(2) 0.012(2) C12 0.030(3) 0.036(3) 0.024(2) 0.003(2) 0.020(2) 0.005(2) C13 0.026(2) 0.038(3) 0.020(2) 0.009(2) 0.014(2) 0.009(2) C14 0.026(2) 0.024(3) 0.020(2) 0.002(2) 0.015(2) 0.005(2) C15 0.021(2) 0.031(3) 0.018(2) 0.003(2) 0.012(2) 0.004(2) C16 0.024(2) 0.022(2) 0.019(2) -0.004(2) 0.011(2) 0.002(2) C17 0.018(2) 0.026(3) 0.018(2) 0.002(2) 0.0068(19) 0.001(2) C18 0.017(2) 0.025(3) 0.019(2) 0.002(2) 0.0087(19) 0.002(2) S19 0.0231(6) 0.0304(7) 0.0226(6) 0.0061(5) 0.0138(5) 0.0043(5) S20 0.0212(6) 0.0266(7) 0.0315(7) 0.0062(5) 0.0119(5) 0.0001(5) C21 0.035(3) 0.038(3) 0.041(3) 0.016(3) 0.027(3) 0.014(2) C22 0.031(3) 0.069(4) 0.074(4) 0.029(4) 0.032(3) 0.017(3) C23 0.041(3) 0.036(3) 0.048(3) 0.007(3) 0.030(3) 0.014(2) C24 0.035(3) 0.044(3) 0.032(3) 0.012(3) 0.013(2) 0.011(3) C25 0.040(3) 0.032(3) 0.037(3) 0.012(2) 0.021(3) 0.006(2) C26 0.051(3) 0.031(3) 0.044(3) 0.007(3) 0.020(3) -0.001(3) C27 0.032(3) 0.045(3) 0.038(3) 0.013(3) 0.024(3) 0.009(2) C28 0.052(4) 0.070(4) 0.050(4) -0.002(3) 0.038(3) -0.007(3) C29 0.035(3) 0.044(3) 0.047(3) 0.018(3) 0.025(3) 0.012(3) C30 0.041(3) 0.035(3) 0.037(3) -0.002(2) 0.024(3) 0.007(2) C31 0.030(3) 0.025(3) 0.034(3) -0.005(2) 0.018(2) -0.004(2) C32 0.041(3) 0.023(3) 0.035(3) 0.005(2) 0.022(2) 0.004(2) S1A 0.0373(8) 0.0359(9) 0.0262(7) -0.0031(7) 0.0137(6) -0.0045(7) O1A 0.0354(19) 0.044(2) 0.0231(17) 0.0036(16) 0.0167(15) 0.0038(16) C1A 0.040(3) 0.047(4) 0.037(3) 0.005(3) 0.013(3) 0.008(3) C2A 0.097(6) 0.058(4) 0.039(4) 0.001(3) 0.047(4) 0.012(4) S1B 0.0287(7) 0.0356(8) 0.0243(7) -0.0031(6) 0.0116(6) 0.0012(6) O1B 0.0288(18) 0.0338(19) 0.0251(17) -0.0021(15) 0.0111(15) 0.0007(15) C1B 0.051(5) 0.056(4) 0.045(4) -0.005(3) 0.031(4) -0.008(3) C2B 0.036(4) 0.085(5) 0.048(4) -0.037(4) 0.016(3) -0.011(4) _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 C4 1.371(5) . ? N1 C1 1.389(5) . ? N1 H1N 0.8799 . ? N2 C8 1.363(5) . ? N2 C5 1.368(5) . ? N2 H2N 0.8800 . ? N3 C14 1.355(5) . ? N3 C11 1.384(5) . ? N3 H3N 0.8799 . ? N4 C18 1.373(5) . ? N4 C15 1.375(5) . ? N4 H4N 0.8798 . ? C1 C2 1.379(6) . ? C1 S20 1.737(5) . ? C2 C3 1.406(6) . ? C2 C21 1.512(6) . ? C3 C4 1.381(6) . ? C3 C23 1.506(6) . ? C4 C5 1.474(6) . ? C5 C6 1.375(6) . ? C6 C7 1.415(6) . ? C6 C24 1.512(6) . ? C7 C8 1.381(6) . ? C7 C25 1.502(6) . ? C8 S9 1.744(4) . ? S9 S10 2.1042(18) . ? S10 C11 1.744(4) . ? C11 C12 1.380(6) . ? C12 C13 1.419(6) . ? C12 C27 1.512(6) . ? C13 C14 1.390(6) . ? C13 C29 1.499(6) . ? C14 C15 1.468(6) . ? C15 C16 1.386(6) . ? C16 C17 1.429(6) . ? C16 C30 1.498(6) . ? C17 C18 1.383(6) . ? C17 C31 1.493(6) . ? C18 S19 1.743(4) . ? S19 S20 2.1096(16) . ? C21 C22 1.539(7) . ? C21 H21A 0.9605 . ? C21 H21B 0.9596 . ? C22 H22A 0.9600 . ? C22 H22B 0.9597 . ? C22 H22C 0.9605 . ? C23 H23C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C24 H24A 0.9603 . ? C24 H24B 0.9599 . ? C24 H24C 0.9603 . ? C25 C26 1.523(7) . ? C25 H25A 0.9600 . ? C25 H25B 0.9601 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9601 . ? C27 C28 1.511(7) . ? C27 H27A 0.9600 . ? C27 H27B 0.9598 . ? C28 H28A 0.9598 . ? C28 H28B 0.9601 . ? C28 H28C 0.9603 . ? C29 H29C 0.9600 . ? C29 H29A 0.9601 . ? C29 H29B 0.9599 . ? C30 H30A 0.9600 . ? C30 H30B 0.9599 . ? C30 H30C 0.9601 . ? C31 C32 1.538(6) . ? C31 H31A 0.9599 . ? C31 H31B 0.9599 . ? C32 H32A 0.9602 . ? C32 H32B 0.9601 . ? C32 H32C 0.9595 . ? S1A O1A 1.503(3) . ? S1A C1A 1.789(5) . ? S1A C2A 1.793(6) . ? S1A H2AE 1.4514 . ? C1A H1AA 0.9599 . ? C1A H1AB 0.9600 . ? C1A H1AC 0.9601 . ? C2A H2AA 0.9601 . ? C2A H2AB 0.9599 . ? C2A H2AC 0.9600 . ? S1AA C2AA 1.7711 . ? S1AA H1AC 1.8437 . ? S1AA H2AB 1.5239 . ? C2AA H2AD 0.9600 . ? C2AA H2AE 0.9600 . ? C2AA H2AF 0.9599 . ? S1B O1B 1.531(3) . ? S1B C1B 1.754(5) . ? S1B C2B 1.776(5) . ? S1B H1BE 1.7613 . ? S1B H2BF 1.3882 . ? C1B H1BA 0.9600 . ? C1B H1BB 0.9599 . ? C1B H1BC 0.9600 . ? C1B H1BD 1.3092 . ? C1B H1BE 0.2739 . ? C1B H1BF 1.4781 . ? C2B H2BA 0.9601 . ? C2B H2BB 0.9601 . ? C2B H2BC 0.9600 . ? C2B H2BE 1.1192 . ? S1BB C1BA 1.7517 . ? S1BB C2BA 1.7709 . ? S1BB H2BB 1.2915 . ? C1BA H1BB 1.2065 . ? C1BA H1BC 0.6197 . ? C1BA H1BD 0.9601 . ? C1BA H1BE 0.9600 . ? C1BA H1BF 0.9600 . ? C2BA H2BA 1.2178 . ? C2BA H2BC 1.3428 . ? C2BA H2BD 0.9599 . ? C2BA H2BE 0.9601 . ? C2BA H2BF 0.9602 . ? 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 C4 N1 C1 108.8(4) . . ? C4 N1 H1N 125.5 . . ? C1 N1 H1N 125.7 . . ? C8 N2 C5 109.0(4) . . ? C8 N2 H2N 125.7 . . ? C5 N2 H2N 125.3 . . ? C14 N3 C11 109.0(4) . . ? C14 N3 H3N 125.7 . . ? C11 N3 H3N 125.3 . . ? C18 N4 C15 108.5(3) . . ? C18 N4 H4N 125.4 . . ? C15 N4 H4N 126.1 . . ? C2 C1 N1 107.3(4) . . ? C2 C1 S20 131.1(3) . . ? N1 C1 S20 121.6(3) . . ? C1 C2 C3 108.2(4) . . ? C1 C2 C21 125.6(4) . . ? C3 C2 C21 126.1(4) . . ? C4 C3 C2 107.1(4) . . ? C4 C3 C23 126.4(4) . . ? C2 C3 C23 126.1(4) . . ? N1 C4 C3 108.5(4) . . ? N1 C4 C5 120.2(4) . . ? C3 C4 C5 131.3(4) . . ? N2 C5 C6 108.1(4) . . ? N2 C5 C4 119.9(4) . . ? C6 C5 C4 131.9(4) . . ? C5 C6 C7 107.6(4) . . ? C5 C6 C24 125.9(4) . . ? C7 C6 C24 126.3(4) . . ? C8 C7 C6 106.6(4) . . ? C8 C7 C25 127.2(4) . . ? C6 C7 C25 126.2(4) . . ? N2 C8 C7 108.7(4) . . ? N2 C8 S9 122.3(3) . . ? C7 C8 S9 129.0(4) . . ? C8 S9 S10 104.82(16) . . ? C11 S10 S9 104.48(16) . . ? C12 C11 N3 108.3(4) . . ? C12 C11 S10 129.8(4) . . ? N3 C11 S10 121.9(3) . . ? C11 C12 C13 107.0(4) . . ? C11 C12 C27 125.3(4) . . ? C13 C12 C27 127.7(4) . . ? C14 C13 C12 107.0(4) . . ? C14 C13 C29 127.3(4) . . ? C12 C13 C29 125.5(4) . . ? N3 C14 C13 108.7(4) . . ? N3 C14 C15 119.8(4) . . ? C13 C14 C15 131.4(4) . . ? N4 C15 C16 108.5(4) . . ? N4 C15 C14 120.0(4) . . ? C16 C15 C14 131.5(4) . . ? C15 C16 C17 107.4(4) . . ? C15 C16 C30 126.6(4) . . ? C17 C16 C30 125.9(4) . . ? C18 C17 C16 106.3(4) . . ? C18 C17 C31 127.5(4) . . ? C16 C17 C31 126.2(4) . . ? N4 C18 C17 109.4(3) . . ? N4 C18 S19 122.1(3) . . ? C17 C18 S19 128.4(3) . . ? C18 S19 S20 104.67(15) . . ? C1 S20 S19 104.81(15) . . ? C2 C21 C22 112.4(4) . . ? C2 C21 H21A 109.1 . . ? C22 C21 H21A 109.0 . . ? C2 C21 H21B 108.9 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 108.1 . . ? C21 C22 H22A 110.5 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 108.9 . . ? H22A C22 H22C 109.4 . . ? H22B C22 H22C 109.5 . . ? C3 C23 H23C 109.6 . . ? C3 C23 H23A 110.1 . . ? H23C C23 H23A 109.5 . . ? C3 C23 H23B 109.7 . . ? H23C C23 H23B 109.5 . . ? H23A C23 H23B 108.3 . . ? C6 C24 H24A 109.1 . . ? C6 C24 H24B 109.3 . . ? H24A C24 H24B 109.5 . . ? C6 C24 H24C 110.0 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C7 C25 C26 112.4(4) . . ? C7 C25 H25A 109.1 . . ? C26 C25 H25A 109.4 . . ? C7 C25 H25B 109.0 . . ? C26 C25 H25B 108.5 . . ? H25A C25 H25B 108.3 . . ? C25 C26 H26A 111.3 . . ? C25 C26 H26B 108.1 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.0 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C12 112.9(4) . . ? C28 C27 H27A 109.2 . . ? C12 C27 H27A 110.0 . . ? C28 C27 H27B 108.1 . . ? C12 C27 H27B 108.1 . . ? H27A C27 H27B 108.3 . . ? C27 C28 H28A 112.0 . . ? C27 C28 H28B 107.6 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 108.8 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.4 . . ? C13 C29 H29C 110.0 . . ? C13 C29 H29A 109.8 . . ? H29C C29 H29A 109.9 . . ? C13 C29 H29B 109.1 . . ? H29C C29 H29B 109.9 . . ? H29A C29 H29B 108.1 . . ? C16 C30 H30A 109.7 . . ? C16 C30 H30B 109.8 . . ? H30A C30 H30B 109.8 . . ? C16 C30 H30C 109.5 . . ? H30A C30 H30C 109.8 . . ? H30B C30 H30C 108.2 . . ? C17 C31 C32 112.3(4) . . ? C17 C31 H31A 109.4 . . ? C32 C31 H31A 108.7 . . ? C17 C31 H31B 109.0 . . ? C32 C31 H31B 109.2 . . ? H31A C31 H31B 108.1 . . ? C31 C32 H32A 110.6 . . ? C31 C32 H32B 109.2 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 108.6 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O1A S1A C1A 105.8(2) . . ? O1A S1A C2A 105.3(3) . . ? C1A S1A C2A 97.2(3) . . ? O1A S1A H2AE 124.5 . . ? C1A S1A H2AE 114.3 . . ? C2A S1A H2AE 105.9 . . ? S1A C1A H1AA 109.6 . . ? S1A C1A H1AB 109.6 . . ? H1AA C1A H1AB 109.5 . . ? S1A C1A H1AC 109.2 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? S1A C2A H2AA 109.4 . . ? S1A C2A H2AB 109.3 . . ? H2AA C2A H2AB 109.5 . . ? S1A C2A H2AC 109.7 . . ? H2AA C2A H2AC 109.5 . . ? H2AB C2A H2AC 109.5 . . ? C2AA S1AA H1AC 118.4 . . ? C2AA S1AA H2AB 103.8 . . ? H1AC S1AA H2AB 99.0 . . ? S1AA C2AA H2AD 109.5 . . ? S1AA C2AA H2AE 109.5 . . ? H2AD C2AA H2AE 109.5 . . ? S1AA C2AA H2AF 109.5 . . ? H2AD C2AA H2AF 109.5 . . ? H2AE C2AA H2AF 109.5 . . ? O1B S1B C1B 107.0(2) . . ? O1B S1B C2B 106.3(2) . . ? C1B S1B C2B 96.2(3) . . ? O1B S1B H1BE 114.0 . . ? C1B S1B H1BE 8.9 . . ? C2B S1B H1BE 98.9 . . ? O1B S1B H2BF 142.3 . . ? C1B S1B H2BF 110.5 . . ? C2B S1B H2BF 73.5 . . ? H1BE S1B H2BF 103.0 . . ? S1B C1B H1BA 109.4 . . ? S1B C1B H1BB 109.4 . . ? H1BA C1B H1BB 109.5 . . ? S1B C1B H1BC 109.6 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? S1B C1B H1BD 113.3 . . ? H1BA C1B H1BD 103.4 . . ? H1BB C1B H1BD 111.8 . . ? H1BC C1B H1BD 6.2 . . ? S1B C1B H1BE 87.1 . . ? H1BA C1B H1BE 73.7 . . ? H1BB C1B H1BE 52.4 . . ? H1BC C1B H1BE 159.8 . . ? H1BD C1B H1BE 158.7 . . ? S1B C1B H1BF 98.6 . . ? H1BA C1B H1BF 151.7 . . ? H1BB C1B H1BF 54.8 . . ? H1BC C1B H1BF 63.2 . . ? H1BD C1B H1BF 68.1 . . ? H1BE C1B H1BF 104.2 . . ? S1B C2B H2BA 109.5 . . ? S1B C2B H2BB 109.5 . . ? H2BA C2B H2BB 109.5 . . ? S1B C2B H2BC 109.4 . . ? H2BA C2B H2BC 109.5 . . ? H2BB C2B H2BC 109.5 . . ? S1B C2B H2BE 96.6 . . ? H2BA C2B H2BE 85.7 . . ? H2BB C2B H2BE 142.2 . . ? H2BC C2B H2BE 33.8 . . ? C1BA S1BB C2BA 95.6 . . ? C1BA S1BB H2BB 87.3 . . ? C2BA S1BB H2BB 80.2 . . ? S1BB C1BA H1BB 127.8 . . ? S1BB C1BA H1BC 113.0 . . ? H1BB C1BA H1BC 114.4 . . ? S1BB C1BA H1BD 109.5 . . ? H1BB C1BA H1BD 120.9 . . ? H1BC C1BA H1BD 10.6 . . ? S1BB C1BA H1BE 109.5 . . ? H1BB C1BA H1BE 42.7 . . ? H1BC C1BA H1BE 98.9 . . ? H1BD C1BA H1BE 109.5 . . ? S1BB C1BA H1BF 109.5 . . ? H1BB C1BA H1BF 66.9 . . ? H1BC C1BA H1BF 115.9 . . ? H1BD C1BA H1BF 109.5 . . ? H1BE C1BA H1BF 109.5 . . ? S1BB C2BA H2BA 74.3 . . ? S1BB C2BA H2BC 84.6 . . ? H2BA C2BA H2BC 75.3 . . ? S1BB C2BA H2BD 109.5 . . ? H2BA C2BA H2BD 57.7 . . ? H2BC C2BA H2BD 122.7 . . ? S1BB C2BA H2BE 109.5 . . ? H2BA C2BA H2BE 80.3 . . ? H2BC C2BA H2BE 25.1 . . ? H2BD C2BA H2BE 109.5 . . ? S1BB C2BA H2BF 109.5 . . ? H2BA C2BA H2BF 166.6 . . ? H2BC C2BA H2BF 117.4 . . ? H2BD C2BA H2BF 109.5 . . ? H2BE C2BA H2BF 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 C4 N1 C1 C2 -0.3(5) . . . . ? C4 N1 C1 S20 -179.9(3) . . . . ? N1 C1 C2 C3 0.2(5) . . . . ? S20 C1 C2 C3 179.8(4) . . . . ? N1 C1 C2 C21 177.0(4) . . . . ? S20 C1 C2 C21 -3.4(7) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C21 C2 C3 C4 -176.9(4) . . . . ? C1 C2 C3 C23 174.1(4) . . . . ? C21 C2 C3 C23 -2.8(8) . . . . ? C1 N1 C4 C3 0.3(5) . . . . ? C1 N1 C4 C5 -177.6(4) . . . . ? C2 C3 C4 N1 -0.1(5) . . . . ? C23 C3 C4 N1 -174.2(4) . . . . ? C2 C3 C4 C5 177.4(4) . . . . ? C23 C3 C4 C5 3.4(8) . . . . ? C8 N2 C5 C6 -0.2(5) . . . . ? C8 N2 C5 C4 -177.1(4) . . . . ? N1 C4 C5 N2 45.2(6) . . . . ? C3 C4 C5 N2 -132.2(5) . . . . ? N1 C4 C5 C6 -130.9(5) . . . . ? C3 C4 C5 C6 51.7(8) . . . . ? N2 C5 C6 C7 -0.7(5) . . . . ? C4 C5 C6 C7 175.8(4) . . . . ? N2 C5 C6 C24 -175.7(4) . . . . ? C4 C5 C6 C24 0.8(8) . . . . ? C5 C6 C7 C8 1.2(5) . . . . ? C24 C6 C7 C8 176.2(4) . . . . ? C5 C6 C7 C25 179.8(4) . . . . ? C24 C6 C7 C25 -5.2(8) . . . . ? C5 N2 C8 C7 0.9(5) . . . . ? C5 N2 C8 S9 -178.9(3) . . . . ? C6 C7 C8 N2 -1.3(5) . . . . ? C25 C7 C8 N2 -179.9(4) . . . . ? C6 C7 C8 S9 178.5(4) . . . . ? C25 C7 C8 S9 0.0(7) . . . . ? N2 C8 S9 S10 -77.6(4) . . . . ? C7 C8 S9 S10 102.6(4) . . . . ? C8 S9 S10 C11 90.1(2) . . . . ? C14 N3 C11 C12 0.6(5) . . . . ? C14 N3 C11 S10 -177.6(3) . . . . ? S9 S10 C11 C12 101.0(4) . . . . ? S9 S10 C11 N3 -81.2(4) . . . . ? N3 C11 C12 C13 -1.7(5) . . . . ? S10 C11 C12 C13 176.3(4) . . . . ? N3 C11 C12 C27 179.3(4) . . . . ? S10 C11 C12 C27 -2.7(8) . . . . ? C11 C12 C13 C14 2.1(5) . . . . ? C27 C12 C13 C14 -178.9(4) . . . . ? C11 C12 C13 C29 177.5(5) . . . . ? C27 C12 C13 C29 -3.6(8) . . . . ? C11 N3 C14 C13 0.8(5) . . . . ? C11 N3 C14 C15 -175.7(4) . . . . ? C12 C13 C14 N3 -1.8(5) . . . . ? C29 C13 C14 N3 -177.0(4) . . . . ? C12 C13 C14 C15 174.2(4) . . . . ? C29 C13 C14 C15 -1.1(8) . . . . ? C18 N4 C15 C16 0.0(5) . . . . ? C18 N4 C15 C14 -176.2(4) . . . . ? N3 C14 C15 N4 42.8(6) . . . . ? C13 C14 C15 N4 -132.8(5) . . . . ? N3 C14 C15 C16 -132.4(5) . . . . ? C13 C14 C15 C16 52.0(8) . . . . ? N4 C15 C16 C17 1.0(5) . . . . ? C14 C15 C16 C17 176.6(4) . . . . ? N4 C15 C16 C30 -175.9(4) . . . . ? C14 C15 C16 C30 -0.3(8) . . . . ? C15 C16 C17 C18 -1.6(5) . . . . ? C30 C16 C17 C18 175.3(4) . . . . ? C15 C16 C17 C31 179.7(4) . . . . ? C30 C16 C17 C31 -3.5(7) . . . . ? C15 N4 C18 C17 -1.1(5) . . . . ? C15 N4 C18 S19 -177.8(3) . . . . ? C16 C17 C18 N4 1.6(5) . . . . ? C31 C17 C18 N4 -179.6(4) . . . . ? C16 C17 C18 S19 178.1(3) . . . . ? C31 C17 C18 S19 -3.2(7) . . . . ? N4 C18 S19 S20 -78.7(3) . . . . ? C17 C18 S19 S20 105.3(4) . . . . ? C2 C1 S20 S19 101.1(4) . . . . ? N1 C1 S20 S19 -79.4(3) . . . . ? C18 S19 S20 C1 90.0(2) . . . . ? C1 C2 C21 C22 106.0(5) . . . . ? C3 C2 C21 C22 -77.7(6) . . . . ? C8 C7 C25 C26 92.9(6) . . . . ? C6 C7 C25 C26 -85.4(6) . . . . ? C11 C12 C27 C28 95.0(6) . . . . ? C13 C12 C27 C28 -83.8(6) . . . . ? C18 C17 C31 C32 107.0(5) . . . . ? C16 C17 C31 C32 -74.5(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 N1 H1N O1A 0.88 2.06 2.872(4) 153.9 . N2 H2N O1B 0.88 2.18 2.934(5) 143.1 . N3 H3N O1A 0.88 2.03 2.834(5) 150.7 . N4 H4N O1B 0.88 2.15 2.949(5) 150.3 . _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.509 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.097 data_s6n3 _database_code_depnum_ccdc_archive 'CCDC 260322' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 N2 O S6' _chemical_formula_weight 506.82 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 18.6529(3) _cell_length_b 8.898(1) _cell_length_c 15.4412(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.589(1) _cell_angle_gamma 90.00 _cell_volume 2545.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.552 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4743 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2921 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0406P)^2^+1.4668P] 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 SHELXL _refine_ls_extinction_coef 0.0029(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2921 _refine_ls_number_parameters 155 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.114 _refine_ls_shift/su_mean 0.006 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 S1 S 0.38324(3) 0.20397(6) 0.08122(3) 0.04850(18) Uani 1 1 d . . . S2 S 0.46805(3) 0.32485(6) 0.04119(3) 0.04770(18) Uani 1 1 d . . . S3 S 0.56140(3) 0.19845(6) 0.06589(3) 0.05025(18) Uani 1 1 d . . . N1 N 0.41375(9) 0.1893(2) 0.25741(10) 0.0383(4) Uani 1 1 d . . . C1 C 0.39948(10) 0.2590(2) 0.33214(13) 0.0417(5) Uani 1 1 d . . . C2 C 0.35272(11) 0.3774(2) 0.31062(14) 0.0457(5) Uani 1 1 d . . . C3 C 0.33874(11) 0.3791(2) 0.21877(14) 0.0453(5) Uani 1 1 d . . . C4 C 0.37701(10) 0.2617(2) 0.18792(13) 0.0409(5) Uani 1 1 d . . . C5 C 0.32221(15) 0.4782(3) 0.37439(17) 0.0682(7) Uani 1 1 d . . . H5A H 0.3106 0.5729 0.3464 0.082 Uiso 1 1 d R . . H5B H 0.3581 0.4961 0.4230 0.082 Uiso 1 1 d R . . C6 C 0.25479(16) 0.4195(4) 0.40568(19) 0.0918(10) Uani 1 1 d . . . H6A H 0.2370 0.4889 0.4458 0.138 Uiso 1 1 d R . . H6B H 0.2184 0.4033 0.3574 0.138 Uiso 1 1 d R . . H6C H 0.2664 0.3257 0.4347 0.138 Uiso 1 1 d R . . C7 C 0.29062(13) 0.4856(3) 0.16382(16) 0.0619(6) Uani 1 1 d . . . H7A H 0.3122 0.5087 0.1119 0.074 Uiso 1 1 d R . . H7B H 0.2874 0.5770 0.1961 0.074 Uiso 1 1 d R . . C8 C 0.21502(13) 0.4263(3) 0.13981(18) 0.0729(8) Uani 1 1 d . . . H8A H 0.1863 0.4988 0.1054 0.109 Uiso 1 1 d R . . H8B H 0.2181 0.3357 0.1067 0.109 Uiso 1 1 d R . . H8C H 0.1931 0.4046 0.1917 0.109 Uiso 1 1 d R . . H1N H 0.4362(11) 0.113(2) 0.2558(13) 0.039(6) Uiso 1 1 d . . . O1A O 0.5000 -0.0783(2) 0.2500 0.0490(5) Uani 1 2 d SU . . C2A C 0.4782(7) -0.1711(19) 0.1704(10) 0.071(4) Uani 0.50 1 d PU . . H2AA H 0.5153 -0.1640 0.1322 0.086 Uiso 0.50 1 d PR . . H2AB H 0.4331 -0.1379 0.1403 0.086 Uiso 0.50 1 d PR . . C3A C 0.4738(7) -0.3175(13) 0.1997(10) 0.095(4) Uani 0.50 1 d PU . . H3AA H 0.5075 -0.3810 0.1746 0.114 Uiso 0.50 1 d PR . . H3AB H 0.4263 -0.3557 0.1819 0.114 Uiso 0.50 1 d PR . . C4A C 0.4880(7) -0.3254(15) 0.2909(10) 0.105(4) Uani 0.50 1 d PU . . H4AA H 0.5286 -0.3896 0.3079 0.126 Uiso 0.50 1 d PR . . H4AB H 0.4467 -0.3644 0.3152 0.126 Uiso 0.50 1 d PR . . C5A C 0.5007(7) -0.1736(15) 0.3224(7) 0.048(2) Uani 0.50 1 d PU . . H5AA H 0.4662 -0.1422 0.3604 0.058 Uiso 0.50 1 d PR . . H5AB H 0.5480 -0.1680 0.3541 0.058 Uiso 0.50 1 d PR . . 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 0.0544(3) 0.0592(4) 0.0303(3) -0.0036(2) -0.0020(2) -0.0051(2) S2 0.0579(3) 0.0539(3) 0.0308(3) 0.0097(2) 0.0028(2) 0.0042(2) S3 0.0566(3) 0.0644(4) 0.0293(3) -0.0054(2) 0.0032(2) 0.0084(3) N1 0.0426(9) 0.0408(10) 0.0313(9) 0.0006(7) 0.0030(7) 0.0044(8) C1 0.0464(11) 0.0470(11) 0.0318(11) -0.0017(9) 0.0047(8) -0.0039(9) C2 0.0499(12) 0.0429(11) 0.0443(12) -0.0051(10) 0.0054(9) -0.0015(9) C3 0.0489(11) 0.0425(11) 0.0431(12) 0.0016(9) -0.0002(9) 0.0010(9) C4 0.0444(11) 0.0452(11) 0.0322(11) 0.0022(9) 0.0004(8) -0.0005(9) C5 0.0863(18) 0.0590(15) 0.0593(16) -0.0173(12) 0.0091(13) 0.0145(13) C6 0.0799(19) 0.132(3) 0.0659(19) -0.0299(19) 0.0204(15) 0.0271(19) C7 0.0745(16) 0.0492(13) 0.0595(15) 0.0039(12) -0.0041(12) 0.0144(12) C8 0.0637(16) 0.0866(18) 0.0650(17) 0.0074(14) -0.0080(13) 0.0209(14) O1A 0.0809(14) 0.0334(10) 0.0314(11) 0.000 0.0002(10) 0.000 C2A 0.076(7) 0.063(5) 0.067(5) -0.034(4) -0.031(4) 0.011(4) C3A 0.163(10) 0.049(6) 0.074(6) -0.018(4) 0.018(8) -0.046(7) C4A 0.180(11) 0.047(5) 0.089(8) 0.011(4) 0.028(9) -0.025(7) C5A 0.074(6) 0.041(4) 0.027(3) 0.002(3) -0.005(4) 0.009(4) _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 S1 C4 1.742(2) . ? S1 S2 2.0655(8) . ? S2 S3 2.0712(8) . ? S3 C1 1.743(2) 2_655 ? N1 C1 1.363(3) . ? N1 C4 1.366(2) . ? N1 H1N 0.80(2) . ? C1 C2 1.383(3) . ? C1 S3 1.743(2) 2_655 ? C2 C3 1.412(3) . ? C2 C5 1.492(3) . ? C3 C4 1.381(3) . ? C3 C7 1.499(3) . ? C5 C6 1.492(4) . ? C5 H5A 0.9599 . ? C5 H5B 0.9601 . ? C6 H6A 0.9601 . ? C6 H6B 0.9601 . ? C6 H6C 0.9600 . ? C7 C8 1.511(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O1A C5A 1.402(14) . ? O1A C5A 1.402(14) 2_655 ? O1A C2A 1.497(16) 2_655 ? O1A C2A 1.497(16) . ? C2A C5A 0.40(2) 2_655 ? C2A C3A 1.384(19) . ? C2A C4A 1.60(2) 2_655 ? C2A H2AA 0.9600 . ? C2A H2AB 0.9601 . ? C3A C4A 0.713(18) 2_655 ? C3A C4A 1.405(9) . ? C3A C5A 1.421(18) 2_655 ? C3A C3A 1.74(3) 2_655 ? C3A H3AA 0.9599 . ? C3A H3AB 0.9601 . ? C4A C3A 0.713(18) 2_655 ? C4A C4A 1.39(3) 2_655 ? C4A C5A 1.446(17) . ? C4A C2A 1.60(2) 2_655 ? C4A H4AA 0.9600 . ? C4A H4AB 0.9601 . ? C5A C2A 0.40(2) 2_655 ? C5A C3A 1.421(18) 2_655 ? C5A H5AA 0.9600 . ? C5A H5AB 0.9599 . ? 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 C4 S1 S2 105.42(7) . . ? S1 S2 S3 108.58(3) . . ? C1 S3 S2 104.73(7) 2_655 . ? C1 N1 C4 108.75(18) . . ? C1 N1 H1N 124.5(15) . . ? C4 N1 H1N 126.4(15) . . ? N1 C1 C2 108.79(18) . . ? N1 C1 S3 121.45(16) . 2_655 ? C2 C1 S3 129.75(16) . 2_655 ? C1 C2 C3 106.75(18) . . ? C1 C2 C5 125.2(2) . . ? C3 C2 C5 128.0(2) . . ? C4 C3 C2 107.16(17) . . ? C4 C3 C7 125.6(2) . . ? C2 C3 C7 127.2(2) . . ? N1 C4 C3 108.55(17) . . ? N1 C4 S1 121.46(15) . . ? C3 C4 S1 129.99(16) . . ? C6 C5 C2 113.7(2) . . ? C6 C5 H5A 107.3 . . ? C2 C5 H5A 108.3 . . ? C6 C5 H5B 110.1 . . ? C2 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C5 C6 H6A 110.5 . . ? C5 C6 H6B 110.4 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 107.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 C8 113.6(2) . . ? C3 C7 H7A 109.1 . . ? C8 C7 H7A 109.8 . . ? C3 C7 H7B 108.1 . . ? C8 C7 H7B 108.1 . . ? H7A C7 H7B 108.0 . . ? C7 C8 H8A 110.3 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.9 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5A O1A C5A 105.6(8) . 2_655 ? C5A O1A C2A 15.3(9) . 2_655 ? C5A O1A C2A 107.3(4) 2_655 2_655 ? C5A O1A C2A 107.3(4) . . ? C5A O1A C2A 15.3(9) 2_655 . ? C2A O1A C2A 113.1(12) 2_655 . ? C5A C2A C3A 87(4) 2_655 . ? C5A C2A O1A 69(4) 2_655 . ? C3A C2A O1A 105.7(11) . . ? C5A C2A C4A 61(4) 2_655 2_655 ? C3A C2A C4A 26.5(7) . 2_655 ? O1A C2A C4A 96.3(9) . 2_655 ? C5A C2A H2AA 54.2 2_655 . ? C3A C2A H2AA 109.7 . . ? O1A C2A H2AA 108.7 . . ? C4A C2A H2AA 90.3 2_655 . ? C5A C2A H2AB 159.7 2_655 . ? C3A C2A H2AB 111.5 . . ? O1A C2A H2AB 111.6 . . ? C4A C2A H2AB 137.0 2_655 . ? H2AA C2A H2AB 109.5 . . ? C4A C3A C2A 94(2) 2_655 . ? C4A C3A C4A 74(3) 2_655 . ? C2A C3A C4A 111.3(13) . . ? C4A C3A C5A 78(2) 2_655 2_655 ? C2A C3A C5A 16.2(9) . 2_655 ? C4A C3A C5A 104.9(12) . 2_655 ? C4A C3A C3A 51.2(19) 2_655 2_655 ? C2A C3A C3A 104.1(8) . 2_655 ? C4A C3A C3A 23.3(8) . 2_655 ? C5A C3A C3A 92.6(8) 2_655 2_655 ? C4A C3A H3AA 48.6 2_655 . ? C2A C3A H3AA 110.8 . . ? C4A C3A H3AA 108.6 . . ? C5A C3A H3AA 100.4 2_655 . ? C3A C3A H3AA 92.0 2_655 . ? C4A C3A H3AB 152.9 2_655 . ? C2A C3A H3AB 109.1 . . ? C4A C3A H3AB 109.4 . . ? C5A C3A H3AB 125.0 2_655 . ? C3A C3A H3AB 131.5 2_655 . ? H3AA C3A H3AB 107.6 . . ? C3A C4A C4A 76(2) 2_655 2_655 ? C3A C4A C3A 105(3) 2_655 . ? C4A C4A C3A 29.6(8) 2_655 . ? C3A C4A C5A 74(2) 2_655 . ? C4A C4A C5A 104.4(9) 2_655 . ? C3A C4A C5A 107.2(13) . . ? C3A C4A C2A 59.9(19) 2_655 2_655 ? C4A C4A C2A 100.7(10) 2_655 2_655 ? C3A C4A C2A 110.6(13) . 2_655 ? C5A C4A C2A 13.9(9) . 2_655 ? C3A C4A H4AA 42.8 2_655 . ? C4A C4A H4AA 85.5 2_655 . ? C3A C4A H4AA 110.8 . . ? C5A C4A H4AA 111.8 . . ? C2A C4A H4AA 98.4 2_655 . ? C3A C4A H4AB 141.7 2_655 . ? C4A C4A H4AB 135.4 2_655 . ? C3A C4A H4AB 110.0 . . ? C5A C4A H4AB 108.3 . . ? C2A C4A H4AB 117.7 2_655 . ? H4AA C4A H4AB 108.8 . . ? C2A C5A O1A 96(5) 2_655 . ? C2A C5A C3A 77(4) 2_655 2_655 ? O1A C5A C3A 109.0(9) . 2_655 ? C2A C5A C4A 105(4) 2_655 . ? O1A C5A C4A 108.1(9) . . ? C3A C5A C4A 28.8(7) 2_655 . ? C2A C5A H5AA 121.7 2_655 . ? O1A C5A H5AA 111.4 . . ? C3A C5A H5AA 132.5 2_655 . ? C4A C5A H5AA 112.4 . . ? C2A C5A H5AB 14.3 2_655 . ? O1A C5A H5AB 107.4 . . ? C3A C5A H5AB 81.7 2_655 . ? C4A C5A H5AB 109.0 . . ? H5AA C5A H5AB 108.4 . . ? 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 C4 S1 S2 S3 92.96(8) . . . . ? S1 S2 S3 C1 -94.09(8) . . . 2_655 ? C4 N1 C1 C2 0.3(2) . . . . ? C4 N1 C1 S3 -178.96(14) . . . 2_655 ? N1 C1 C2 C3 -0.4(2) . . . . ? S3 C1 C2 C3 178.76(16) 2_655 . . . ? N1 C1 C2 C5 177.8(2) . . . . ? S3 C1 C2 C5 -3.0(3) 2_655 . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C5 C2 C3 C4 -177.8(2) . . . . ? C1 C2 C3 C7 179.4(2) . . . . ? C5 C2 C3 C7 1.2(4) . . . . ? C1 N1 C4 C3 0.0(2) . . . . ? C1 N1 C4 S1 179.38(14) . . . . ? C2 C3 C4 N1 -0.2(2) . . . . ? C7 C3 C4 N1 -179.23(19) . . . . ? C2 C3 C4 S1 -179.55(16) . . . . ? C7 C3 C4 S1 1.4(3) . . . . ? S2 S1 C4 N1 -90.65(16) . . . . ? S2 S1 C4 C3 88.6(2) . . . . ? C1 C2 C5 C6 -86.6(3) . . . . ? C3 C2 C5 C6 91.2(3) . . . . ? C4 C3 C7 C8 84.1(3) . . . . ? C2 C3 C7 C8 -94.7(3) . . . . ? C5A O1A C2A C5A -86(4) . . . 2_655 ? C2A O1A C2A C5A -71(4) 2_655 . . 2_655 ? C5A O1A C2A C3A -5.3(14) . . . . ? C5A O1A C2A C3A 80(4) 2_655 . . . ? C2A O1A C2A C3A 9.8(7) 2_655 . . . ? C5A O1A C2A C4A -30.5(13) . . . 2_655 ? C5A O1A C2A C4A 55(3) 2_655 . . 2_655 ? C2A O1A C2A C4A -15.4(6) 2_655 . . 2_655 ? C5A C2A C3A C4A -5(5) 2_655 . . 2_655 ? O1A C2A C3A C4A -72(3) . . . 2_655 ? C5A C2A C3A C4A 69(4) 2_655 . . . ? O1A C2A C3A C4A 2.3(15) . . . . ? C4A C2A C3A C4A 74(2) 2_655 . . . ? O1A C2A C3A C5A -67(4) . . . 2_655 ? C4A C2A C3A C5A 5(5) 2_655 . . 2_655 ? C5A C2A C3A C3A 46(4) 2_655 . . 2_655 ? O1A C2A C3A C3A -21.0(15) . . . 2_655 ? C4A C2A C3A C3A 50.9(18) 2_655 . . 2_655 ? C4A C3A C4A C3A 12(4) 2_655 . . 2_655 ? C2A C3A C4A C3A -76(3) . . . 2_655 ? C5A C3A C4A C3A -60(3) 2_655 . . 2_655 ? C2A C3A C4A C4A -87.6(18) . . . 2_655 ? C5A C3A C4A C4A -72.0(16) 2_655 . . 2_655 ? C3A C3A C4A C4A -12(4) 2_655 . . 2_655 ? C4A C3A C4A C5A 89(2) 2_655 . . . ? C2A C3A C4A C5A 1.4(15) . . . . ? C5A C3A C4A C5A 17.1(17) 2_655 . . . ? C3A C3A C4A C5A 77(2) 2_655 . . . ? C4A C3A C4A C2A 75(2) 2_655 . . 2_655 ? C2A C3A C4A C2A -12.8(19) . . . 2_655 ? C5A C3A C4A C2A 2.9(16) 2_655 . . 2_655 ? C3A C3A C4A C2A 63(2) 2_655 . . 2_655 ? C5A O1A C5A C2A 99(4) 2_655 . . 2_655 ? C2A O1A C5A C2A 115(4) . . . 2_655 ? C5A O1A C5A C3A 20.8(7) 2_655 . . 2_655 ? C2A O1A C5A C3A -78(4) 2_655 . . 2_655 ? C2A O1A C5A C3A 36.6(14) . . . 2_655 ? C5A O1A C5A C4A -9.6(7) 2_655 . . . ? C2A O1A C5A C4A -108(4) 2_655 . . . ? C2A O1A C5A C4A 6.2(14) . . . . ? C3A C4A C5A C2A -5(5) 2_655 . . 2_655 ? C4A C4A C5A C2A -76(5) 2_655 . . 2_655 ? C3A C4A C5A C2A -107(4) . . . 2_655 ? C3A C4A C5A O1A 97(2) 2_655 . . . ? C4A C4A C5A O1A 25.8(16) 2_655 . . . ? C3A C4A C5A O1A -4.9(14) . . . . ? C2A C4A C5A O1A 102(5) 2_655 . . . ? C4A C4A C5A C3A -71(2) 2_655 . . 2_655 ? C3A C4A C5A C3A -102(2) . . . 2_655 ? C2A C4A C5A C3A 5(5) 2_655 . . 2_655 ? 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 O1A 0.80(2) 2.09(2) 2.884(2) 177(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.242 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.048