# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Bing Gong.' 'Yu An.' 'Wen Feng.' 'Oksana Gerlitz' 'Lan He.' 'Kazuhiro Yamato' 'Lihua Yuan.' 'Chong Zheng.' _publ_contact_author_name 'Prof Bing Gong' _publ_contact_author_address ; Department of Chemistry State University of New York at Buffalo Natural Sciences Complex Buffalo NY 14260 UNITED STATES OF AMERICA ; _publ_contact_author_email BGONG@BUFFALO.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Macrocyclic aromatic tetrasulfonamides with a stable cone conformation ; data_4a _database_code_depnum_ccdc_archive 'CCDC 266730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H73 N7 O19 S4' _chemical_formula_weight 1192.38 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 32.684(3) _cell_length_b 20.741(2) _cell_length_c 8.9393(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.263(2) _cell_angle_gamma 90.00 _cell_volume 6034.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 294 _cell_measurement_theta_min -14 _cell_measurement_theta_max 14 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.590061 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD PLATFORM' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20841 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10243 _reflns_number_gt 9108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART and SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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. (1999). J. Appl. Cryst. 32, 115-119. Bruker (1999). SMART and SAINT. Data Collection and Reduction Software for the SMART System. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Sheldrick, G.M. (2000). SADABS. Program for Empirical Absorption Correction of Area Detector Data. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXTL. Version 5.1. Bruker Analytical X-Ray Systems, Madison, Wisconsin, USA. ; _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^)+(0.0271P)^2^+22.8573P] 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 SHELXL _refine_ls_extinction_coef 0.00000(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details '(Flack, 1983)' _refine_ls_abs_structure_Flack 0.43(18) _refine_ls_number_reflns 10243 _refine_ls_number_parameters 786 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0907 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1678 _refine_ls_goodness_of_fit_ref 1.262 _refine_ls_restrained_S_all 1.265 _refine_ls_shift/su_max 5.277 _refine_ls_shift/su_mean 0.105 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 0.85188(7) -0.01082(11) 0.1519(2) 0.0461(5) Uani 1 1 d . . . S2 S 0.85144(7) 0.25157(10) 0.1553(3) 0.0539(6) Uani 1 1 d . . . S3 S 0.66962(6) 0.25337(10) 0.2574(2) 0.0383(5) Uani 1 1 d . . . S4 S 0.67275(7) -0.00916(10) 0.2583(2) 0.0447(5) Uani 1 1 d . . . N1 N 0.8269(2) -0.0559(3) 0.0238(9) 0.0504(19) Uani 1 1 d . . . H1 H 0.8400 -0.0853 -0.0197 0.024(17) Uiso 1 1 calc R . . N2 N 0.8254(2) 0.3012(4) 0.0372(8) 0.0462(18) Uani 1 1 d . . . H2 H 0.8377 0.3350 0.0083 0.6(3) Uiso 1 1 calc R . . N3 N 0.6796(2) 0.3027(3) 0.1164(7) 0.0343(15) Uani 1 1 d . . . H3 H 0.6654 0.3375 0.1023 0.40(13) Uiso 1 1 calc R . . N4 N 0.6795(2) -0.0536(3) 0.1165(8) 0.0439(17) Uani 1 1 d . . . H4 H 0.6613 -0.0828 0.0934 0.05(3) Uiso 1 1 calc R . . C11 C 0.8612(2) 0.0618(4) 0.0702(8) 0.0323(16) Uani 1 1 d . . . O11 O 0.89087(19) -0.0409(3) 0.1975(8) 0.0593(18) Uani 1 1 d . . . C12 C 0.85109(15) 0.1161(5) 0.1230(6) 0.0382(15) Uani 1 1 d . . . H12 H 0.8373 0.1175 0.2094 0.064(18) Uiso 1 1 calc R . . O12 O 0.8271(2) 0.0056(4) 0.2713(7) 0.0620(19) Uani 1 1 d . . . C13 C 0.8612(3) 0.1769(5) 0.0479(11) 0.053(2) Uani 1 1 d . . . C14 C 0.88057(19) 0.1760(4) -0.0741(9) 0.038(2) Uani 1 1 d . . . C15 C 0.88861(18) 0.1193(5) -0.1412(6) 0.0531(18) Uani 1 1 d . . . H15 H 0.8997 0.1196 -0.2334 0.025(12) Uiso 1 1 calc R . . C16 C 0.8803(3) 0.0604(4) -0.0733(11) 0.057(3) Uani 1 1 d . . . C21 C 0.7832(2) 0.2913(3) -0.0201(9) 0.0288(16) Uani 1 1 d . . . C31 C 0.6481(2) 0.1794(3) 0.1855(8) 0.0358(18) Uani 1 1 d . . . O21 O 0.8896(2) 0.2832(4) 0.1784(9) 0.075(2) Uani 1 1 d . . . O22 O 0.8248(2) 0.2382(3) 0.2694(7) 0.0586(18) Uani 1 1 d . . . C22 C 0.7517(3) 0.2951(4) 0.0804(9) 0.051(2) Uani 1 1 d . . . H22 H 0.7581 0.3013 0.1830 0.004(12) Uiso 1 1 calc R . . C23 C 0.7111(3) 0.2891(4) 0.0182(12) 0.058(2) Uani 1 1 d . . . C24 C 0.6995(4) 0.2862(4) -0.1409(9) 0.064(3) Uani 1 1 d . . . C25 C 0.7302(2) 0.2868(3) -0.2318(10) 0.0358(18) Uani 1 1 d . . . H25 H 0.7242 0.2851 -0.3355 0.10(4) Uiso 1 1 calc R . . C26 C 0.7702(2) 0.2899(3) -0.1718(10) 0.0408(19) Uani 1 1 d . . . O31 O 0.63892(14) 0.2821(3) 0.3317(6) 0.0363(12) Uani 1 1 d . . . C32 C 0.6676(2) 0.1250(5) 0.2311(5) 0.051(2) Uani 1 1 d . . . H32 H 0.6912 0.1277 0.2971 0.015(11) Uiso 1 1 calc R . . O32 O 0.70893(17) 0.2400(3) 0.3408(6) 0.0468(15) Uani 1 1 d . . . C33 C 0.6534(2) 0.0644(5) 0.1823(8) 0.048(2) Uani 1 1 d . . . C34 C 0.6152(4) 0.0604(5) 0.0873(11) 0.080(3) Uani 1 1 d . . . C35 C 0.59756(17) 0.1252(5) 0.0338(6) 0.0413(14) Uani 1 1 d . . . H35 H 0.5742 0.1270 -0.0341 0.029(12) Uiso 1 1 calc R . . C36 C 0.61489(14) 0.1770(3) 0.0824(7) 0.0146(12) Uani 1 1 d . . . C41 C 0.7131(2) -0.0491(3) 0.0245(6) 0.0236(15) Uani 1 1 d . . . O41 O 0.6402(2) -0.0443(3) 0.3298(7) 0.073(2) Uani 1 1 d . . . C42 C 0.7539(2) -0.0493(3) 0.0742(8) 0.0298(16) Uani 1 1 d . . . H42 H 0.7611 -0.0503 0.1773 0.21(7) Uiso 1 1 calc R . . O42 O 0.71000(18) 0.0055(3) 0.3387(6) 0.0577(18) Uani 1 1 d . . . C43 C 0.7845(3) -0.0481(5) -0.0176(10) 0.054(2) Uani 1 1 d . . . C44 C 0.7751(3) -0.0429(4) -0.1777(7) 0.0396(19) Uani 1 1 d . . . C45 C 0.7339(3) -0.0416(5) -0.2298(8) 0.054(3) Uani 1 1 d . . . H45 H 0.7264 -0.0385 -0.3324 0.07(3) Uiso 1 1 calc R . . C46 C 0.70256(17) -0.0448(4) -0.1265(9) 0.0288(16) Uani 1 1 d . . . O141 O 0.8889(3) 0.2396(4) -0.1276(8) 0.076(2) Uani 1 1 d . . . C142 C 0.9047(3) 0.2482(5) -0.2609(10) 0.059(2) Uani 1 1 d . . . H14A H 0.8849 0.2340 -0.3416 0.10(4) Uiso 1 1 calc R . . H14B H 0.9293 0.2223 -0.2637 0.07(3) Uiso 1 1 calc R . . C143 C 0.9148(4) 0.3167(5) -0.2835(12) 0.069(3) Uani 1 1 d . . . H14C H 0.9349 0.3304 -0.2031 0.08(4) Uiso 1 1 calc R . . H14D H 0.8902 0.3425 -0.2780 0.19(8) Uiso 1 1 calc R . . C144 C 0.9324(4) 0.3293(6) -0.4376(13) 0.079(4) Uani 1 1 d . . . H14E H 0.9381 0.3744 -0.4473 0.27(11) Uiso 1 1 calc R . . H14F H 0.9126 0.3161 -0.5177 0.19(8) Uiso 1 1 calc R . . H14G H 0.9573 0.3051 -0.4423 0.15(6) Uiso 1 1 calc R . . O161 O 0.89077(18) 0.0065(2) -0.1226(7) 0.0440(14) Uani 1 1 d . . . C162 C 0.9062(3) 0.0025(5) -0.2761(12) 0.062(3) Uani 1 1 d . . . H16A H 0.9305 0.0288 -0.2815 0.015(14) Uiso 1 1 calc R . . H16B H 0.8853 0.0163 -0.3533 0.021(17) Uiso 1 1 calc R . . C163 C 0.9163(4) -0.0701(6) -0.2939(17) 0.085(4) Uani 1 1 d . . . H16C H 0.9348 -0.0836 -0.2086 0.16(8) Uiso 1 1 calc R . . H16D H 0.8912 -0.0948 -0.2924 0.09(4) Uiso 1 1 calc R . . C164 C 0.9343(6) -0.0842(9) -0.4257(19) 0.139(7) Uani 1 1 d . . . H16E H 0.9397 -0.1296 -0.4301 0.08(3) Uiso 1 1 calc R . . H16F H 0.9597 -0.0609 -0.4268 1.6(10) Uiso 1 1 calc R . . H16G H 0.9160 -0.0718 -0.5109 0.05(2) Uiso 1 1 calc R . . O241 O 0.65996(12) 0.2866(3) -0.1762(6) 0.0463(15) Uani 1 1 d . . . C242 C 0.6496(4) 0.2907(6) -0.3316(9) 0.075(3) Uani 1 1 d . . . H24A H 0.6202 0.2902 -0.3518 0.017(16) Uiso 1 1 calc R . . H24B H 0.6611 0.2546 -0.3804 0.12(5) Uiso 1 1 calc R . . H24C H 0.6603 0.3300 -0.3690 0.03(2) Uiso 1 1 calc R . . O261 O 0.80419(19) 0.2846(4) -0.2595(7) 0.0534(16) Uani 1 1 d . . . C262 C 0.7972(5) 0.3008(10) -0.4144(13) 0.108(5) Uani 1 1 d . . . H26A H 0.8227 0.2997 -0.4593 0.09(4) Uiso 1 1 calc R . . H26B H 0.7856 0.3433 -0.4243 0.20(9) Uiso 1 1 calc R . . H26C H 0.7785 0.2703 -0.4640 0.20(8) Uiso 1 1 calc R . . O341 O 0.5998(2) 0.0035(3) 0.0404(7) 0.0554(16) Uani 1 1 d . . . C342 C 0.5649(3) -0.0006(4) -0.0686(10) 0.051(2) Uani 1 1 d . . . H34A H 0.5703 0.0229 -0.1585 0.07(3) Uiso 1 1 calc R . . H34B H 0.5411 0.0185 -0.0286 0.004(13) Uiso 1 1 calc R . . C343 C 0.5565(3) -0.0697(4) -0.1066(13) 0.063(3) Uani 1 1 d . . . H34C H 0.5822 -0.0901 -0.1252 0.06(3) Uiso 1 1 calc R . . H34D H 0.5467 -0.0906 -0.0195 0.09(4) Uiso 1 1 calc R . . C344 C 0.5273(6) -0.0818(8) -0.234(2) 0.144(7) Uani 1 1 d . . . H34E H 0.5232 -0.1274 -0.2450 0.010(13) Uiso 1 1 calc R . . H34F H 0.5376 -0.0646 -0.3226 0.23(11) Uiso 1 1 calc R . . H34G H 0.5017 -0.0615 -0.2179 0.09(5) Uiso 1 1 calc R . . O361 O 0.59800(15) 0.2362(3) 0.0526(6) 0.0406(14) Uani 1 1 d . . . C362 C 0.5676(2) 0.2419(5) -0.0754(12) 0.058(3) Uani 1 1 d . . . H36A H 0.5427 0.2185 -0.0583 0.05(2) Uiso 1 1 calc R . . H36B H 0.5782 0.2257 -0.1660 0.08(3) Uiso 1 1 calc R . . C363 C 0.5595(3) 0.3152(6) -0.0863(11) 0.068(3) Uani 1 1 d . . . H36C H 0.5844 0.3378 -0.1066 0.09(4) Uiso 1 1 calc R . . H36D H 0.5506 0.3312 0.0075 0.04(2) Uiso 1 1 calc R . . C364 C 0.5244(4) 0.3266(5) -0.2197(14) 0.070(3) Uani 1 1 d . . . H36E H 0.5188 0.3719 -0.2295 0.31(12) Uiso 1 1 calc R . . H36F H 0.4999 0.3043 -0.1981 0.11(5) Uiso 1 1 calc R . . H36G H 0.5335 0.3106 -0.3118 0.10(4) Uiso 1 1 calc R . . O441 O 0.8055(2) -0.0464(4) -0.2641(7) 0.0601(18) Uani 1 1 d . . . C442 C 0.7961(3) -0.0600(6) -0.4208(10) 0.061(3) Uani 1 1 d . . . H44A H 0.8207 -0.0566 -0.4714 0.07(3) Uiso 1 1 calc R . . H44B H 0.7762 -0.0296 -0.4634 0.013(14) Uiso 1 1 calc R . . H44C H 0.7853 -0.1029 -0.4327 0.08(4) Uiso 1 1 calc R . . O461 O 0.6610(2) -0.0421(4) -0.1743(6) 0.071(2) Uani 1 1 d . . . C462 C 0.6467(3) -0.0483(8) -0.3336(12) 0.080(4) Uani 1 1 d . . . H46A H 0.6172 -0.0485 -0.3453 0.09(4) Uiso 1 1 calc R . . H46B H 0.6569 -0.0878 -0.3721 0.17(7) Uiso 1 1 calc R . . H46C H 0.6567 -0.0125 -0.3880 0.14(7) Uiso 1 1 calc R . . C5 C 0.6900(5) 0.1187(11) -0.256(2) 0.270(14) Uani 1 1 d D . . H5 H 0.6760 0.1127 -0.1713 2.0(12) Uiso 1 1 calc R . . N5 N 0.7313(3) 0.1205(6) -0.2402(8) 0.102(3) Uani 1 1 d D . . O5 O 0.6712(3) 0.1241(10) -0.3698(13) 0.198(5) Uani 1 1 d D . . C51 C 0.7417(6) 0.1235(9) -0.0908(12) 0.158(6) Uani 1 1 d D . . H51A H 0.7172 0.1249 -0.0392 0.41(15) Uiso 1 1 calc R . . H51B H 0.7577 0.1616 -0.0676 0.32(12) Uiso 1 1 calc R . . H51C H 0.7575 0.0861 -0.0592 0.05(2) Uiso 1 1 calc R . . C52 C 0.7572(7) 0.1265(9) -0.3378(17) 0.37(2) Uani 1 1 d D . . H52A H 0.7845 0.1201 -0.2906 0.11(3) Uiso 1 1 calc R . . H52B H 0.7550 0.1689 -0.3808 0.29(10) Uiso 1 1 calc R . . H52C H 0.7516 0.0949 -0.4154 0.027(16) Uiso 1 1 calc R . . C6 C 0.5225(4) 0.1017(11) 0.2884(13) 0.148(10) Uani 1 1 d D . . H6 H 0.5244 0.0576 0.2722 0.23(11) Uiso 1 1 calc R . . N6 N 0.5487(2) 0.1274(6) 0.3920(7) 0.080(2) Uani 1 1 d D . . O6 O 0.4975(3) 0.1297(10) 0.2162(10) 0.177(5) Uani 1 1 d D . . C61 C 0.5681(7) 0.0800(12) 0.470(2) 0.42(4) Uani 1 1 d D . . H61A H 0.5546 0.0398 0.4452 0.09(3) Uiso 1 1 calc R . . H61B H 0.5676 0.0882 0.5757 0.09(3) Uiso 1 1 calc R . . H61C H 0.5960 0.0778 0.4459 0.16(6) Uiso 1 1 calc R . . C62 C 0.5595(8) 0.1847(10) 0.426(3) 0.29(2) Uani 1 1 d D . . H62A H 0.5862 0.1842 0.4802 0.09(4) Uiso 1 1 calc R . . H62B H 0.5401 0.2035 0.4874 0.33(14) Uiso 1 1 calc R . . H62C H 0.5604 0.2096 0.3358 0.15(5) Uiso 1 1 calc R . . C7 C 0.9429(4) 0.1501(9) -0.5890(14) 0.134(6) Uani 1 1 d D . . H7 H 0.9371 0.1940 -0.5921 0.24(11) Uiso 1 1 calc R . . N7 N 0.9607(2) 0.1246(9) -0.7047(9) 0.115(4) Uani 1 1 d D . . O7 O 0.9340(3) 0.1207(9) -0.4832(10) 0.167(4) Uani 1 1 d D . . C71 C 0.9778(7) 0.1789(10) -0.755(3) 0.34(3) Uani 1 1 d D . . H71A H 0.9737 0.2138 -0.6876 0.5(2) Uiso 1 1 calc R . . H71B H 0.9650 0.1892 -0.8533 0.001(11) Uiso 1 1 calc R . . H71C H 1.0067 0.1721 -0.7605 0.39(17) Uiso 1 1 calc R . . C72 C 0.9706(4) 0.0716(10) -0.768(3) 0.222(13) Uani 1 1 d D . . H72A H 0.9998 0.0654 -0.7515 0.24(11) Uiso 1 1 calc R . . H72B H 0.9626 0.0738 -0.8737 0.13(5) Uiso 1 1 calc R . . H72C H 0.9568 0.0361 -0.7250 0.36(18) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0486(11) 0.0525(14) 0.0368(11) 0.0063(11) 0.0008(9) -0.0017(10) S2 0.0652(13) 0.0325(12) 0.0603(15) -0.0082(11) -0.0148(11) 0.0072(11) S3 0.0432(10) 0.0414(12) 0.0291(10) 0.0036(9) -0.0035(8) -0.0101(9) S4 0.0695(13) 0.0359(12) 0.0291(10) 0.0082(9) 0.0078(9) -0.0023(10) N1 0.064(4) 0.022(4) 0.062(5) -0.006(3) -0.011(4) -0.021(3) N2 0.059(4) 0.042(4) 0.041(4) -0.016(3) 0.022(3) -0.018(3) N3 0.062(4) 0.018(3) 0.021(3) -0.004(2) -0.002(3) 0.008(3) N4 0.050(4) 0.028(4) 0.055(4) -0.012(3) 0.017(3) 0.006(3) C11 0.056(4) 0.024(4) 0.017(3) 0.003(3) 0.006(3) -0.007(3) O11 0.061(4) 0.041(4) 0.070(4) 0.018(3) -0.024(3) -0.006(3) C12 0.034(3) 0.035(4) 0.044(3) 0.023(4) -0.004(2) 0.011(4) O12 0.070(4) 0.075(5) 0.043(4) 0.015(4) 0.014(3) 0.002(4) C13 0.042(4) 0.048(5) 0.067(6) -0.009(5) -0.013(4) -0.008(4) C14 0.015(3) 0.065(6) 0.039(4) 0.002(4) 0.024(3) -0.013(3) C15 0.051(4) 0.059(4) 0.051(3) 0.017(5) 0.015(3) 0.050(5) C16 0.085(6) 0.005(4) 0.076(6) -0.004(4) -0.020(5) -0.016(4) C21 0.040(4) 0.001(3) 0.043(4) 0.004(3) -0.008(3) 0.004(3) C31 0.064(5) 0.005(3) 0.036(4) 0.012(3) -0.009(3) 0.027(3) O21 0.058(4) 0.083(5) 0.078(5) -0.013(4) -0.018(3) -0.010(4) O22 0.090(5) 0.053(4) 0.034(3) 0.008(3) 0.006(3) 0.031(4) C22 0.080(6) 0.042(5) 0.030(4) -0.023(4) -0.003(4) -0.017(4) C23 0.066(5) 0.032(5) 0.078(7) 0.007(5) 0.020(5) -0.014(4) C24 0.146(9) 0.031(5) 0.015(4) 0.005(3) 0.003(5) -0.014(5) C25 0.038(4) 0.011(3) 0.057(5) 0.006(3) -0.004(3) -0.014(3) C26 0.046(4) 0.009(3) 0.070(6) -0.003(3) 0.018(4) -0.009(3) O31 0.025(2) 0.047(3) 0.037(3) -0.002(3) 0.001(2) 0.011(2) C32 0.078(5) 0.050(4) 0.025(3) -0.011(4) 0.009(3) -0.073(5) O32 0.060(3) 0.045(3) 0.036(3) 0.009(3) 0.011(2) -0.036(3) C33 0.041(4) 0.081(6) 0.024(4) 0.013(4) 0.022(3) 0.047(4) C34 0.151(10) 0.057(6) 0.036(5) -0.005(5) 0.030(6) 0.009(7) C35 0.046(3) 0.046(4) 0.031(3) 0.010(5) -0.001(2) 0.012(5) C36 0.000(2) 0.013(3) 0.030(3) 0.003(3) -0.005(2) 0.016(2) C41 0.047(4) 0.019(3) 0.003(3) 0.009(2) -0.011(3) -0.008(3) O41 0.132(6) 0.051(4) 0.043(3) 0.019(3) 0.040(4) 0.025(4) C42 0.043(4) 0.014(3) 0.034(4) -0.014(3) 0.008(3) -0.011(3) O42 0.066(4) 0.067(4) 0.033(3) 0.007(3) -0.033(3) -0.028(3) C43 0.068(6) 0.058(6) 0.038(5) 0.013(4) 0.007(4) 0.015(5) C44 0.060(5) 0.050(5) 0.010(3) 0.003(3) 0.011(3) -0.016(4) C45 0.080(6) 0.082(7) 0.002(3) 0.008(4) 0.009(3) -0.013(5) C46 0.004(2) 0.034(4) 0.047(4) 0.007(3) -0.003(3) 0.003(3) O141 0.096(5) 0.079(5) 0.055(4) 0.017(4) 0.021(4) -0.010(4) C142 0.085(6) 0.053(6) 0.038(4) 0.004(4) 0.005(4) -0.001(5) C143 0.117(10) 0.036(5) 0.053(6) 0.001(5) 0.002(6) -0.009(6) C144 0.113(10) 0.072(8) 0.055(7) 0.016(5) 0.028(7) 0.011(7) O161 0.049(3) 0.011(3) 0.075(4) 0.001(3) 0.025(3) -0.004(2) C162 0.051(5) 0.042(5) 0.101(8) -0.001(5) 0.047(5) -0.014(4) C163 0.086(8) 0.075(8) 0.100(10) -0.033(7) 0.041(8) 0.004(7) C164 0.172(15) 0.130(13) 0.112(12) -0.020(10) -0.011(10) 0.109(12) O241 0.0074(19) 0.080(4) 0.046(3) 0.008(3) -0.026(2) -0.004(2) C242 0.107(8) 0.101(9) 0.013(4) 0.020(5) -0.008(4) 0.010(7) O261 0.055(3) 0.064(4) 0.040(3) -0.007(3) 0.003(3) -0.014(3) C262 0.108(10) 0.175(17) 0.040(7) -0.001(8) 0.000(7) 0.019(11) O341 0.077(4) 0.036(4) 0.051(4) -0.001(3) -0.006(3) -0.012(3) C342 0.077(6) 0.038(5) 0.037(4) -0.001(4) -0.005(4) 0.007(4) C343 0.087(7) 0.022(4) 0.074(7) -0.014(4) -0.026(5) -0.001(4) C344 0.135(16) 0.145(14) 0.147(17) -0.077(13) -0.022(12) -0.066(13) O361 0.029(2) 0.054(4) 0.037(3) 0.007(3) -0.003(2) -0.006(2) C362 0.021(3) 0.076(7) 0.077(7) 0.012(6) -0.002(4) 0.028(4) C363 0.048(5) 0.108(9) 0.048(5) -0.008(5) 0.009(4) 0.024(5) C364 0.073(7) 0.052(6) 0.084(8) -0.002(5) 0.000(6) 0.004(5) O441 0.071(4) 0.068(5) 0.044(3) -0.002(3) 0.022(3) -0.022(4) C442 0.066(6) 0.079(8) 0.042(5) -0.007(5) 0.031(4) 0.024(6) O461 0.122(6) 0.072(5) 0.023(3) 0.010(3) 0.027(3) 0.015(4) C462 0.019(4) 0.144(12) 0.074(7) -0.002(8) -0.008(4) 0.027(6) C5 0.30(2) 0.075(9) 0.39(3) 0.05(2) -0.22(2) -0.095(17) N5 0.142(7) 0.061(5) 0.093(5) 0.018(7) -0.045(5) -0.060(7) O5 0.175(8) 0.150(8) 0.245(11) -0.017(17) -0.108(8) 0.021(14) C51 0.299(18) 0.057(6) 0.112(8) 0.023(10) -0.016(11) -0.072(14) C52 0.81(6) 0.045(9) 0.31(2) 0.060(16) 0.40(3) 0.13(2) C6 0.101(10) 0.25(3) 0.089(9) 0.019(12) 0.000(7) -0.027(13) N6 0.074(4) 0.100(6) 0.065(4) -0.007(6) -0.004(3) -0.054(6) O6 0.119(7) 0.265(14) 0.138(7) 0.031(13) -0.042(5) 0.059(12) C61 0.52(6) 0.55(8) 0.21(2) 0.19(3) 0.20(3) 0.45(6) C62 0.37(4) 0.27(3) 0.27(3) -0.16(3) 0.26(3) -0.18(3) C7 0.131(12) 0.17(2) 0.102(10) 0.022(10) 0.016(9) 0.018(10) N7 0.074(5) 0.183(11) 0.088(6) -0.069(9) 0.009(4) -0.028(9) O7 0.222(10) 0.163(8) 0.125(7) -0.029(11) 0.065(7) -0.093(12) C71 0.21(3) 0.21(3) 0.56(7) 0.17(4) -0.15(3) -0.13(2) C72 0.043(7) 0.24(3) 0.37(4) -0.14(2) -0.049(13) -0.016(11) _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 O12 1.439(7) . ? S1 O11 1.444(6) . ? S1 N1 1.637(7) . ? S1 C11 1.713(8) . ? S2 O21 1.407(7) . ? S2 O22 1.428(7) . ? S2 N2 1.654(8) . ? S2 C13 1.864(10) . ? S3 O31 1.387(5) . ? S3 O32 1.451(6) . ? S3 N3 1.679(7) . ? S3 C31 1.783(8) . ? S4 O42 1.389(6) . ? S4 O41 1.483(8) . ? S4 N4 1.598(7) . ? S4 C33 1.763(8) . ? N1 C43 1.411(11) . ? N2 C21 1.441(10) . ? N3 C23 1.440(12) . ? N4 C41 1.435(10) . ? C11 C12 1.276(12) . ? C11 C16 1.478(13) . ? C12 C13 1.480(13) . ? C13 C14 1.310(12) . ? C14 C15 1.357(13) . ? C14 O141 1.438(11) . ? C15 C16 1.402(13) . ? C16 O161 1.259(11) . ? C21 C26 1.383(12) . ? C21 C22 1.428(12) . ? C31 C32 1.339(12) . ? C31 C36 1.360(9) . ? C22 C23 1.398(13) . ? C23 C24 1.439(14) . ? C24 O241 1.303(13) . ? C24 C25 1.348(13) . ? C25 C26 1.369(11) . ? C26 O261 1.420(10) . ? C32 C33 1.396(13) . ? C33 C34 1.446(15) . ? C34 O341 1.335(13) . ? C34 C35 1.524(15) . ? C35 C36 1.272(12) . ? C36 O361 1.362(8) . ? C41 C46 1.366(10) . ? C41 C42 1.367(10) . ? C42 C43 1.350(11) . ? C43 C44 1.439(11) . ? C44 O441 1.313(10) . ? C44 C45 1.385(12) . ? C45 C46 1.443(10) . ? C46 O461 1.388(9) . ? O141 C142 1.353(12) . ? C142 C143 1.476(14) . ? C143 C144 1.562(16) . ? O161 C162 1.508(11) . ? C162 C163 1.551(15) . ? C163 C164 1.40(2) . ? O241 C242 1.402(9) . ? O261 C262 1.423(13) . ? O341 C342 1.433(10) . ? C342 C343 1.493(12) . ? C343 C344 1.435(17) . ? O361 C362 1.450(10) . ? C362 C363 1.545(15) . ? C363 C364 1.593(15) . ? O441 C442 1.435(11) . ? O461 C462 1.463(12) . ? C5 O5 1.141(13) . ? C5 N5 1.347(15) . ? N5 C52 1.275(12) . ? N5 C51 1.348(10) . ? C6 O6 1.151(15) . ? C6 N6 1.314(13) . ? N6 C62 1.268(16) . ? N6 C61 1.333(14) . ? C7 O7 1.183(13) . ? C7 N7 1.341(13) . ? N7 C72 1.292(15) . ? N7 C71 1.352(15) . ? 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 O12 S1 O11 115.8(4) . . ? O12 S1 N1 112.1(4) . . ? O11 S1 N1 108.8(4) . . ? O12 S1 C11 104.0(4) . . ? O11 S1 C11 108.3(4) . . ? N1 S1 C11 107.5(4) . . ? O21 S2 O22 125.1(5) . . ? O21 S2 N2 101.7(4) . . ? O22 S2 N2 105.3(4) . . ? O21 S2 C13 105.7(5) . . ? O22 S2 C13 110.6(4) . . ? N2 S2 C13 106.9(4) . . ? O31 S3 O32 118.8(3) . . ? O31 S3 N3 107.3(4) . . ? O32 S3 N3 106.1(3) . . ? O31 S3 C31 105.3(4) . . ? O32 S3 C31 108.8(3) . . ? N3 S3 C31 110.6(3) . . ? O42 S4 O41 120.9(4) . . ? O42 S4 N4 111.0(4) . . ? O41 S4 N4 102.4(4) . . ? O42 S4 C33 106.0(4) . . ? O41 S4 C33 110.2(4) . . ? N4 S4 C33 105.3(4) . . ? C43 N1 S1 122.3(7) . . ? C21 N2 S2 124.0(5) . . ? C23 N3 S3 122.5(6) . . ? C41 N4 S4 125.8(6) . . ? C12 C11 C16 118.9(7) . . ? C12 C11 S1 123.8(6) . . ? C16 C11 S1 117.3(6) . . ? C11 C12 C13 120.6(6) . . ? C14 C13 C12 120.7(9) . . ? C14 C13 S2 124.0(8) . . ? C12 C13 S2 114.7(7) . . ? C13 C14 C15 120.6(8) . . ? C13 C14 O141 112.6(8) . . ? C15 C14 O141 126.7(7) . . ? C14 C15 C16 120.7(6) . . ? O161 C16 C15 123.5(9) . . ? O161 C16 C11 118.1(7) . . ? C15 C16 C11 118.2(7) . . ? C26 C21 C22 116.5(6) . . ? C26 C21 N2 123.2(7) . . ? C22 C21 N2 119.2(7) . . ? C32 C31 C36 120.2(6) . . ? C32 C31 S3 117.1(5) . . ? C36 C31 S3 122.6(4) . . ? C23 C22 C21 117.2(8) . . ? C22 C23 N3 116.5(9) . . ? C22 C23 C24 123.4(9) . . ? N3 C23 C24 118.3(9) . . ? O241 C24 C25 129.1(8) . . ? O241 C24 C23 113.8(9) . . ? C25 C24 C23 117.0(10) . . ? C24 C25 C26 120.1(9) . . ? C25 C26 C21 125.5(8) . . ? C25 C26 O261 123.1(8) . . ? C21 C26 O261 111.0(7) . . ? C31 C32 C33 122.0(6) . . ? C32 C33 C34 118.6(8) . . ? C32 C33 S4 124.2(6) . . ? C34 C33 S4 115.8(8) . . ? O341 C34 C33 121.1(10) . . ? O341 C34 C35 124.1(10) . . ? C33 C34 C35 114.5(9) . . ? C36 C35 C34 119.6(6) . . ? C35 C36 C31 124.4(6) . . ? C35 C36 O361 122.3(5) . . ? C31 C36 O361 112.6(5) . . ? C46 C41 C42 118.1(6) . . ? C46 C41 N4 115.7(6) . . ? C42 C41 N4 126.1(6) . . ? C43 C42 C41 123.8(7) . . ? C42 C43 N1 127.0(8) . . ? C42 C43 C44 120.3(8) . . ? N1 C43 C44 112.5(8) . . ? O441 C44 C45 124.5(7) . . ? O441 C44 C43 118.6(8) . . ? C45 C44 C43 116.5(7) . . ? C44 C45 C46 120.7(6) . . ? C41 C46 O461 117.2(6) . . ? C41 C46 C45 120.4(6) . . ? O461 C46 C45 122.4(7) . . ? C142 O141 C14 120.9(8) . . ? O141 C142 C143 110.9(9) . . ? C142 C143 C144 112.8(9) . . ? C16 O161 C162 119.5(7) . . ? O161 C162 C163 103.9(8) . . ? C164 C163 C162 113.6(12) . . ? C24 O241 C242 112.7(7) . . ? C26 O261 C262 117.1(9) . . ? C34 O341 C342 121.4(8) . . ? O341 C342 C343 109.3(7) . . ? C344 C343 C342 116.3(10) . . ? C36 O361 C362 117.6(6) . . ? O361 C362 C363 103.4(8) . . ? C362 C363 C364 107.5(9) . . ? C44 O441 C442 118.8(7) . . ? C46 O461 C462 120.7(6) . . ? O5 C5 N5 123.0(19) . . ? C52 N5 C51 123.5(13) . . ? C52 N5 C5 130.6(13) . . ? C51 N5 C5 105.4(13) . . ? O6 C6 N6 125(2) . . ? C62 N6 C6 134.2(18) . . ? C62 N6 C61 117.2(14) . . ? C6 N6 C61 108.5(16) . . ? O7 C7 N7 124.7(18) . . ? C72 N7 C7 144.7(19) . . ? C72 N7 C71 115.8(14) . . ? C7 N7 C71 98.8(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.370 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.063