# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global # SUBMISSION DETAILS _publ_contact_author_name 'Dr A.J. Blake' _publ_contact_author_address ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD England UK ; _publ_contact_author_email A.J.Blake@nottingham.ac.uk _publ_contact_author_fax '0115 951 3563' _publ_contact_author_phone '0115 951 3488' _publ_requested_journal 'Chemistry - A European Journal' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Design and Synthesis of Functionalised Aza-Thioether Macrocycles for Heteroditopic Metal Extraction ; loop_ _publ_author_name 'Mark W. Glenny' 'Marie Lacombe' 'Jason B. Love' 'Alexander J. Blake' 'Leonard F. Lindoy' 'Robert C. Luckay' 'Karsten Gloe' 'Bianca Antonellic' 'Claire Wilson' 'Martin Schr\"oder' data_(1) #CDS3OP _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N2 O2 S3' _chemical_formula_sum 'C16 H22 N2 O2 S3' _chemical_formula_weight 370.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4753(10) _cell_length_b 12.7836(13) _cell_length_c 15.653(2) _cell_angle_alpha 73.346(2) _cell_angle_beta 81.158(2) _cell_angle_gamma 86.034(2) _cell_volume 1794.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1449 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.73 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.423 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10218 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.166 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.90 _reflns_number_total 7810 _reflns_number_gt 3814 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL; PLATON (Spek, 2001)' _refine_special_details ; ? ; _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^)+(0.0267P)^2^] 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 7809 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.131 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.105 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _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 S1 S 0.14422(11) 0.68018(8) 1.28928(6) 0.0273(3) Uani 1 1 d . . . O1 O 0.1343(3) 0.6635(2) 0.99121(15) 0.0245(6) Uani 1 1 d . . . N1 N 0.1709(3) 0.8247(2) 1.01679(18) 0.0181(7) Uani 1 1 d . . . C1 C 0.1046(4) 0.7818(3) 1.1110(2) 0.0216(9) Uani 1 1 d . . . H1A H 0.0202 0.7393 1.1128 0.026 Uiso 1 1 calc R . . H1B H 0.0712 0.8437 1.1358 0.026 Uiso 1 1 calc R . . O2 O 0.0953(2) 0.9575(2) 0.83502(15) 0.0224(6) Uani 1 1 d . . . N2 N 0.2307(3) 0.7991(2) 0.87170(18) 0.0198(7) Uani 1 1 d . . . H2A H 0.3041 0.7634 0.8505 0.024 Uiso 1 1 calc R . . S2 S 0.27570(11) 1.00383(8) 1.30123(6) 0.0271(3) Uani 1 1 d . . . C2 C 0.2077(4) 0.7091(3) 1.1698(2) 0.0250(9) Uani 1 1 d . . . H2B H 0.3008 0.7452 1.1569 0.030 Uiso 1 1 calc R . . H2C H 0.2235 0.6393 1.1538 0.030 Uiso 1 1 calc R . . S3 S 0.30329(11) 1.12906(8) 1.00272(6) 0.0251(2) Uani 1 1 d . . . C3 C 0.1374(4) 0.8148(3) 1.3077(2) 0.0260(9) Uani 1 1 d . . . H3A H 0.0798 0.8650 1.2647 0.031 Uiso 1 1 calc R . . H3B H 0.0882 0.8097 1.3693 0.031 Uiso 1 1 calc R . . C4 C 0.2838(4) 0.8633(3) 1.2967(2) 0.0264(9) Uani 1 1 d . . . H4A H 0.3379 0.8596 1.2383 0.032 Uiso 1 1 calc R . . H4B H 0.3369 0.8183 1.3449 0.032 Uiso 1 1 calc R . . C5 C 0.2323(4) 1.0750(3) 1.1895(2) 0.0241(9) Uani 1 1 d . . . H5A H 0.1517 1.0383 1.1776 0.029 Uiso 1 1 calc R . . H5B H 0.2002 1.1506 1.1884 0.029 Uiso 1 1 calc R . . C6 C 0.3563(4) 1.0789(3) 1.1145(2) 0.0213(9) Uani 1 1 d . . . H6A H 0.3995 1.0046 1.1218 0.026 Uiso 1 1 calc R . . H6B H 0.4302 1.1268 1.1200 0.026 Uiso 1 1 calc R . . C7 C 0.1845(4) 1.0242(3) 1.0026(2) 0.0199(9) Uani 1 1 d . . . H7A H 0.1145 1.0095 1.0582 0.024 Uiso 1 1 calc R . . H7B H 0.1309 1.0509 0.9506 0.024 Uiso 1 1 calc R . . C8 C 0.2646(4) 0.9186(3) 0.9971(2) 0.0194(9) Uani 1 1 d . . . H8A H 0.3185 0.9296 0.9359 0.023 Uiso 1 1 calc R . . H8B H 0.3348 0.9013 1.0403 0.023 Uiso 1 1 calc R . . C9 C 0.1752(4) 0.7588(3) 0.9642(2) 0.0188(8) Uani 1 1 d . . . C10 C 0.1782(4) 0.8900(3) 0.8124(2) 0.0191(8) Uani 1 1 d . . . C11 C 0.2326(4) 0.8964(3) 0.7162(2) 0.0176(8) Uani 1 1 d . . . C12 C 0.3759(4) 0.8764(3) 0.6890(2) 0.0215(9) Uani 1 1 d . . . H12A H 0.4414 0.8589 0.7316 0.026 Uiso 1 1 calc R . . C13 C 0.4236(4) 0.8820(3) 0.5993(2) 0.0305(10) Uani 1 1 d . . . H13A H 0.5217 0.8688 0.5805 0.037 Uiso 1 1 calc R . . C14 C 0.3282(5) 0.9068(4) 0.5376(3) 0.0374(11) Uani 1 1 d . . . H14A H 0.3608 0.9097 0.4764 0.045 Uiso 1 1 calc R . . C15 C 0.1860(5) 0.9274(4) 0.5641(3) 0.0416(12) Uani 1 1 d . . . H15A H 0.1210 0.9446 0.5212 0.050 Uiso 1 1 calc R . . C16 C 0.1374(4) 0.9232(3) 0.6534(2) 0.0301(10) Uani 1 1 d . . . H16A H 0.0396 0.9385 0.6715 0.036 Uiso 1 1 calc R . . S1' S 0.25428(12) 0.61081(9) 0.50475(6) 0.0321(3) Uani 1 1 d . . . O1' O 0.3147(3) 0.6376(2) 0.78928(15) 0.0245(6) Uani 1 1 d . . . N1' N 0.3258(3) 0.4721(2) 0.76707(18) 0.0197(7) Uani 1 1 d . . . C1' C 0.3560(4) 0.5244(3) 0.6699(2) 0.0232(9) Uani 1 1 d . . . H1'A H 0.4029 0.4699 0.6401 0.028 Uiso 1 1 calc R . . H1'B H 0.4239 0.5837 0.6592 0.028 Uiso 1 1 calc R . . O2' O 0.4534(3) 0.3691(2) 0.94310(15) 0.0262(6) Uani 1 1 d . . . N2' N 0.2690(3) 0.4949(2) 0.91400(18) 0.0188(7) Uani 1 1 d . . . H2'A H 0.1903 0.5211 0.9391 0.023 Uiso 1 1 calc R . . S2' S 0.23104(12) 0.26611(9) 0.49646(7) 0.0360(3) Uani 1 1 d . . . C2' C 0.2240(4) 0.5715(3) 0.6269(2) 0.0273(10) Uani 1 1 d . . . H2'B H 0.1888 0.6363 0.6473 0.033 Uiso 1 1 calc R . . H2'C H 0.1482 0.5166 0.6483 0.033 Uiso 1 1 calc R . . S3' S 0.33114(10) 0.14894(8) 0.77791(6) 0.0232(2) Uani 1 1 d . . . C3' C 0.2982(4) 0.4812(3) 0.4802(2) 0.0279(10) Uani 1 1 d . . . H3'A H 0.3283 0.4953 0.4146 0.033 Uiso 1 1 calc R . . H3'B H 0.3806 0.4469 0.5109 0.033 Uiso 1 1 calc R . . C4' C 0.1778(4) 0.4014(3) 0.5086(2) 0.0296(10) Uani 1 1 d . . . H4'A H 0.1003 0.4312 0.4719 0.035 Uiso 1 1 calc R . . H4'B H 0.1390 0.3944 0.5723 0.035 Uiso 1 1 calc R . . C5' C 0.3319(4) 0.2138(3) 0.5900(2) 0.0275(10) Uani 1 1 d . . . H5'A H 0.3868 0.1474 0.5828 0.033 Uiso 1 1 calc R . . H5'B H 0.4011 0.2690 0.5886 0.033 Uiso 1 1 calc R . . C6' C 0.2371(4) 0.1861(3) 0.6810(2) 0.0225(9) Uani 1 1 d . . . H6'A H 0.1761 0.1248 0.6844 0.027 Uiso 1 1 calc R . . H6'B H 0.1733 0.2499 0.6842 0.027 Uiso 1 1 calc R . . C7' C 0.3975(4) 0.2789(3) 0.7758(2) 0.0212(9) Uani 1 1 d . . . H7'A H 0.4622 0.2671 0.8219 0.025 Uiso 1 1 calc R . . H7'B H 0.4537 0.3110 0.7162 0.025 Uiso 1 1 calc R . . C8' C 0.2781(4) 0.3587(3) 0.7935(2) 0.0194(9) Uani 1 1 d . . . H8'A H 0.1996 0.3544 0.7596 0.023 Uiso 1 1 calc R . . H8'B H 0.2399 0.3373 0.8584 0.023 Uiso 1 1 calc R . . C9' C 0.3055(4) 0.5382(3) 0.8204(2) 0.0191(8) Uani 1 1 d . . . C10' C 0.3456(4) 0.4143(3) 0.9711(2) 0.0203(9) Uani 1 1 d . . . C11' C 0.2865(4) 0.3924(3) 1.0677(2) 0.0221(9) Uani 1 1 d . . . C12' C 0.1396(4) 0.3972(3) 1.0956(2) 0.0279(10) Uani 1 1 d . . . H12B H 0.0755 0.4173 1.0521 0.033 Uiso 1 1 calc R . . C13' C 0.0871(4) 0.3725(3) 1.1866(3) 0.0359(11) Uani 1 1 d . . . H13B H -0.0130 0.3735 1.2057 0.043 Uiso 1 1 calc R . . C14' C 0.1810(5) 0.3466(3) 1.2494(3) 0.0381(11) Uani 1 1 d . . . H14B H 0.1451 0.3318 1.3117 0.046 Uiso 1 1 calc R . . C15' C 0.3259(4) 0.3418(3) 1.2228(2) 0.0310(10) Uani 1 1 d . . . H15B H 0.3898 0.3245 1.2664 0.037 Uiso 1 1 calc R . . C16' C 0.3785(4) 0.3624(3) 1.1319(2) 0.0255(9) Uani 1 1 d . . . H16B H 0.4783 0.3559 1.1136 0.031 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 0.0352(7) 0.0246(6) 0.0192(5) -0.0020(4) -0.0032(4) -0.0004(5) O1 0.0329(17) 0.0176(16) 0.0232(15) -0.0061(12) -0.0019(12) -0.0046(12) N1 0.0193(18) 0.0194(18) 0.0165(16) -0.0062(14) 0.0013(13) -0.0088(14) C1 0.022(2) 0.024(2) 0.018(2) -0.0053(17) 0.0005(16) -0.0028(18) O2 0.0226(15) 0.0212(15) 0.0245(14) -0.0092(12) -0.0035(11) 0.0045(12) N2 0.0175(18) 0.0215(18) 0.0182(17) -0.0036(14) -0.0009(13) 0.0035(14) S2 0.0279(6) 0.0319(7) 0.0236(6) -0.0094(5) -0.0075(4) -0.0005(5) C2 0.027(2) 0.027(2) 0.021(2) -0.0069(18) -0.0021(17) 0.0027(18) S3 0.0315(6) 0.0205(6) 0.0236(5) -0.0049(5) -0.0042(4) -0.0065(5) C3 0.028(2) 0.031(2) 0.019(2) -0.0092(18) -0.0032(17) 0.0019(19) C4 0.023(2) 0.029(2) 0.026(2) -0.0051(19) -0.0058(17) 0.0021(18) C5 0.025(2) 0.024(2) 0.023(2) -0.0033(18) -0.0075(17) 0.0005(18) C6 0.024(2) 0.021(2) 0.020(2) -0.0067(17) -0.0042(16) -0.0041(17) C7 0.021(2) 0.020(2) 0.020(2) -0.0048(17) -0.0059(16) -0.0022(17) C8 0.015(2) 0.021(2) 0.021(2) -0.0052(17) 0.0013(16) -0.0057(17) C9 0.017(2) 0.023(2) 0.017(2) -0.0055(17) -0.0053(16) 0.0014(17) C10 0.014(2) 0.020(2) 0.026(2) -0.0088(18) -0.0049(16) -0.0057(17) C11 0.022(2) 0.014(2) 0.0165(19) -0.0047(16) -0.0008(16) -0.0009(16) C12 0.023(2) 0.019(2) 0.020(2) -0.0005(17) -0.0037(17) -0.0030(17) C13 0.025(2) 0.033(3) 0.029(2) -0.008(2) 0.0044(19) 0.0039(19) C14 0.039(3) 0.050(3) 0.021(2) -0.008(2) -0.003(2) 0.010(2) C15 0.043(3) 0.058(3) 0.031(3) -0.020(2) -0.019(2) 0.011(2) C16 0.026(2) 0.035(3) 0.033(2) -0.014(2) -0.0090(19) 0.008(2) S1' 0.0433(7) 0.0286(6) 0.0213(6) -0.0020(5) -0.0068(5) 0.0041(5) O1' 0.0358(17) 0.0147(15) 0.0215(14) -0.0039(12) -0.0022(12) 0.0000(12) N1' 0.0270(19) 0.0138(18) 0.0170(17) -0.0036(14) 0.0010(14) -0.0034(14) C1' 0.027(2) 0.023(2) 0.019(2) -0.0058(18) -0.0027(17) 0.0022(18) O2' 0.0226(16) 0.0292(17) 0.0271(15) -0.0079(13) -0.0055(12) 0.0014(13) N2' 0.0173(18) 0.0206(18) 0.0170(17) -0.0039(14) -0.0015(13) 0.0018(14) S2' 0.0481(8) 0.0355(7) 0.0283(6) -0.0134(5) -0.0135(5) 0.0088(6) C2' 0.034(3) 0.031(3) 0.018(2) -0.0090(18) -0.0034(18) 0.0050(19) S3' 0.0277(6) 0.0168(5) 0.0250(5) -0.0042(4) -0.0066(4) 0.0001(4) C3' 0.027(2) 0.036(3) 0.019(2) -0.0060(19) -0.0056(17) 0.006(2) C4' 0.027(2) 0.032(3) 0.027(2) -0.006(2) -0.0076(18) 0.011(2) C5' 0.030(2) 0.028(2) 0.023(2) -0.0055(18) -0.0058(18) 0.0074(19) C6' 0.030(2) 0.017(2) 0.023(2) -0.0084(17) -0.0060(17) 0.0018(17) C7' 0.025(2) 0.016(2) 0.024(2) -0.0076(17) -0.0053(17) -0.0030(17) C8' 0.021(2) 0.020(2) 0.019(2) -0.0082(17) -0.0050(16) 0.0008(17) C9' 0.014(2) 0.020(2) 0.023(2) -0.0058(18) -0.0030(16) 0.0007(17) C10' 0.022(2) 0.019(2) 0.025(2) -0.0117(18) -0.0045(17) -0.0058(18) C11' 0.024(2) 0.019(2) 0.023(2) -0.0056(18) -0.0019(17) -0.0012(17) C12' 0.028(2) 0.029(3) 0.027(2) -0.0070(19) -0.0095(18) 0.0039(19) C13' 0.023(3) 0.047(3) 0.034(3) -0.008(2) 0.001(2) 0.004(2) C14' 0.049(3) 0.043(3) 0.019(2) -0.005(2) -0.005(2) 0.001(2) C15' 0.032(3) 0.037(3) 0.026(2) -0.006(2) -0.0152(19) 0.001(2) C16' 0.022(2) 0.027(2) 0.030(2) -0.0097(19) -0.0090(18) 0.0014(18) 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 C1 1.473(4) . y N1 C8 1.475(4) . y N1 C9 1.331(4) . y N2 C9 1.420(4) . y N2 C10 1.379(4) . y O1 C9 1.239(4) . y O2 C10 1.217(4) . y S1 C2 1.812(3) . y S1 C3 1.821(4) . y S2 C4 1.814(4) . y S2 C5 1.820(3) . y S3 C6 1.819(3) . y S3 C7 1.810(3) . y C1 C2 1.526(5) . ? C3 C4 1.524(5) . ? C5 C6 1.520(4) . ? C7 C8 1.520(5) . ? C10 C11 1.496(4) . ? C11 C12 1.388(5) . ? C11 C16 1.391(5) . ? C12 C13 1.390(5) . ? C13 C14 1.380(5) . ? C14 C15 1.378(5) . ? C15 C16 1.390(5) . ? N1' C1' 1.467(4) . y N1' C8' 1.472(4) . y N1' C9' 1.335(4) . y N2' C10' 1.399(5) . y N2' C9' 1.406(4) . y O1' C9' 1.228(4) . y O2' C10' 1.222(4) . y S1' C2' 1.815(3) . y S1' C3' 1.812(4) . y S2' C4' 1.821(4) . y S2' C5' 1.812(4) . y S3' C6' 1.807(4) . y S3' C7' 1.806(3) . y C1' C2' 1.517(5) . ? C3' C4' 1.512(5) . ? C5' C6' 1.524(4) . ? C7' C8' 1.518(5) . ? C10' C11' 1.482(5) . ? C11' C16' 1.386(5) . ? C11' C12' 1.396(5) . ? C12' C13' 1.387(5) . ? C13' C14' 1.382(5) . ? C14' C15' 1.374(5) . ? C15' C16' 1.388(5) . ? 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 N1 C1 C2 112.3(3) . . ? N1 C8 C7 113.6(3) . . ? N1 C9 N2 118.5(3) . . ? N2 C10 C11 112.6(3) . . ? O1 C9 N1 123.9(3) . . ? O1 C9 N2 117.5(3) . . ? O2 C10 N2 124.3(3) . . ? O2 C10 C11 123.1(3) . . ? C1 N1 C8 116.5(3) . . y C1 N1 C9 116.7(3) . . y C9 N1 C8 123.8(3) . . y C10 N2 C9 125.0(3) . . y C2 S1 C3 102.61(17) . . y C4 S2 C5 100.83(17) . . y C7 S3 C6 101.94(16) . . y C1 C2 S1 113.2(2) . . ? C3 C4 S2 113.5(3) . . ? C4 C3 S1 113.8(3) . . ? C5 C6 S3 113.0(3) . . ? C6 C5 S2 113.8(3) . . ? C8 C7 S3 112.2(2) . . ? C11 C12 C13 120.0(3) . . ? C12 C11 C10 121.1(3) . . ? C12 C11 C16 119.9(3) . . ? C14 C13 C12 120.0(4) . . ? C14 C15 C16 120.2(4) . . ? C15 C14 C13 120.3(4) . . ? C15 C16 C11 119.6(4) . . ? C16 C11 C10 119.0(3) . . ? N1' C1' C2' 113.6(3) . . ? N1' C8' C7' 112.6(3) . . ? N1' C9' N2' 120.2(3) . . ? N2' C10' C11' 113.6(3) . . ? O1' C9' N1' 121.2(3) . . ? O1' C9' N2' 118.6(3) . . ? O2' C10' N2' 122.4(3) . . ? O2' C10' C11' 124.0(4) . . ? C1' N1' C8' 115.8(3) . . y C1' N1' C9' 116.7(3) . . y C9' N1' C8' 124.7(3) . . y C10' N2' C9' 126.4(3) . . y C2' S1' C3' 102.57(18) . . y C4' S2' C5' 100.81(18) . . y C7' S3' C6' 101.86(17) . . y C1' C2' S1' 113.8(2) . . ? C3' C4' S2' 113.8(3) . . ? C4' C3' S1' 114.7(3) . . ? C5' C6' S3' 115.3(2) . . ? C6' C5' S2' 112.8(2) . . ? C8' C7' S3' 112.4(2) . . ? C11' C12' C13' 120.1(4) . . ? C12' C11' C10' 121.4(3) . . ? C12' C11' C16' 119.2(3) . . ? C16' C11' C10' 119.3(3) . . ? C14' C13' C12' 119.7(4) . . ? C14' C15' C16' 119.7(4) . . ? C15' C14' C13' 120.7(4) . . ? C15' C16' C11' 120.5(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 C1 N1 C8 C7 -70.7(4) . . . . y C1 N1 C9 O1 -3.9(5) . . . . ? C1 N1 C9 N2 176.4(3) . . . . ? C2 S1 C3 C4 -68.0(3) . . . . y C3 S1 C2 C1 -63.7(3) . . . . y C4 S2 C5 C6 -73.1(3) . . . . y C5 S2 C4 C3 -77.0(3) . . . . y C6 S3 C7 C8 -72.1(3) . . . . y C7 S3 C6 C5 -64.4(3) . . . . y C8 N1 C1 C2 -79.1(4) . . . . y C8 N1 C9 O1 155.7(3) . . . . ? C8 N1 C9 N2 -23.9(5) . . . . ? C9 N1 C1 C2 82.1(4) . . . . ? C9 N1 C8 C7 129.7(4) . . . . ? C9 N2 C10 O2 13.6(5) . . . . ? C9 N2 C10 C11 -165.5(3) . . . . ? C10 N2 C9 N1 -58.0(5) . . . . ? C10 N2 C9 O1 122.3(4) . . . . ? C10 C11 C12 C13 179.5(3) . . . . ? C10 C11 C16 C15 -178.8(3) . . . . ? C11 C12 C13 C14 -0.4(6) . . . . ? C12 C11 C16 C15 1.4(6) . . . . ? C12 C13 C14 C15 0.8(7) . . . . ? C13 C14 C15 C16 -0.1(7) . . . . ? C14 C15 C16 C11 -1.0(6) . . . . ? C16 C11 C12 C13 -0.7(5) . . . . ? N1 C1 C2 S1 166.9(2) . . . . y N2 C10 C11 C12 -44.8(5) . . . . ? N2 C10 C11 C16 135.3(3) . . . . ? O2 C10 C11 C12 136.0(4) . . . . ? O2 C10 C11 C16 -43.8(5) . . . . ? S1 C3 C4 S2 172.71(18) . . . . y S2 C5 C6 S3 170.10(19) . . . . y S3 C7 C8 N1 167.3(2) . . . . y C1' N1' C8' C7' 71.6(4) . . . . y C1' N1' C9' O1' -1.5(5) . . . . ? C1' N1' C9' N2' 176.9(3) . . . . ? C2' S1' C3' C4' 65.2(3) . . . . y C3' S1' C2' C1' 64.5(3) . . . . y C4' S2' C5' C6' 72.3(3) . . . . y C5' S2' C4' C3' 73.8(3) . . . . y C6' S3' C7' C8' 66.1(3) . . . . y C7' S3' C6' C5' 72.4(3) . . . . y C8' N1' C1' C2' 82.8(4) . . . . y C8' N1' C9' O1' -161.7(3) . . . . ? C8' N1' C9' N2' 16.7(5) . . . . ? C9' N1' C1' C2' -79.1(4) . . . . ? C9' N1' C8' C7' -128.0(4) . . . . ? C9' N2' C10' O2' -2.9(6) . . . . ? C9' N2' C10' C11' 175.1(3) . . . . ? C10' N2' C9' N1' 55.8(5) . . . . ? C10' N2' C9' O1' -125.8(4) . . . . ? C10' C11' C12' C13' 177.7(3) . . . . ? C10' C11' C16' C15' 179.8(3) . . . . ? C11' C12' C13' C14' 2.0(6) . . . . ? C12' C13' C14' C15' -1.9(7) . . . . ? C12' C11' C16' C15' -2.7(6) . . . . ? C13' C14' C15' C16' -0.5(6) . . . . ? C14' C15' C16' C11' 2.9(6) . . . . ? C16' C11' C12' C13' 0.3(6) . . . . ? N1' C1' C2' S1' -168.1(2) . . . . y N2' C10' C11' C12' 35.4(5) . . . . ? N2' C10' C11' C16' -147.2(3) . . . . ? O2' C10' C11' C12' -146.6(4) . . . . ? O2' C10' C11' C16' 30.8(5) . . . . ? S1' C3' C4' S2' -172.56(19) . . . . y S2' C5' C6' S3' -172.95(19) . . . . y S3' C7' C8' N1' -163.8(2) . . . . y 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 N2 H2A O1' 0.88 2.08 2.746(4) 131 . N2' H2'A O1 0.88 2.20 2.893(4) 135 . _diffrn_measured_fraction_theta_max 0.827 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.48 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.08 #===END of CIF data_(2) #S3NOPH _exptl_special_details ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N2 O S4' _chemical_formula_sum 'C16 H22 N2 O S4' _chemical_formula_weight 386.60 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 'P 21/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 13.450(3) _cell_length_b 7.195(2) _cell_length_c 20.096(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.53(3) _cell_angle_gamma 90.00 _cell_volume 1864.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 12.6 _cell_measurement_theta_max 17.5 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.514 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details 'X-RED version 1.09 (Stoe, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-6.3' _diffrn_reflns_number 4071 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3666 _reflns_number_gt 3153 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'STADI-4 version 1.07 (Stoe, 1997a)' _computing_cell_refinement STADI-4 _computing_data_reduction 'X-RED version 1.09 (Stoe, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL; PLATON (Spek, 2000)' _refine_special_details ; ? ; _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^)+(0.0290P)^2^+1.9328P] 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 3666 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 S1 S 0.11555(4) 0.07058(8) 1.00679(3) 0.02069(14) Uani 1 1 d . . . O1 O -0.19952(11) 0.3485(2) 0.92882(8) 0.0195(3) Uani 1 1 d . . . N1 N -0.02993(13) 0.4670(3) 0.86501(9) 0.0163(4) Uani 1 1 d . . . C1 C 0.01020(17) 0.2840(3) 0.89428(11) 0.0176(4) Uani 1 1 d . . . H1B H 0.0693 0.2489 0.8767 0.021 Uiso 1 1 calc R . . H1C H -0.0448 0.1895 0.8777 0.021 Uiso 1 1 calc R . . N2 N -0.19745(14) 0.3485(3) 0.81571(9) 0.0191(4) Uani 1 1 d . . . H2A H -0.2200 0.2888 0.7760 0.023 Uiso 1 1 calc R . . S2 S 0.41059(4) 0.32994(9) 0.99728(3) 0.02407(15) Uani 1 1 d . . . C2 C 0.04575(16) 0.2814(3) 0.97358(11) 0.0172(4) Uani 1 1 d . . . H2B H -0.0155 0.2921 0.9914 0.021 Uiso 1 1 calc R . . H2C H 0.0911 0.3899 0.9906 0.021 Uiso 1 1 calc R . . S3 S 0.22643(4) 0.75483(8) 0.85105(3) 0.02083(14) Uani 1 1 d . . . C3 C 0.23617(16) 0.1081(3) 0.98553(12) 0.0197(5) Uani 1 1 d . . . H3A H 0.2775 -0.0078 0.9943 0.024 Uiso 1 1 calc R . . H3B H 0.2206 0.1373 0.9355 0.024 Uiso 1 1 calc R . . S4 S -0.15912(5) 0.67428(9) 0.76762(3) 0.03084(16) Uani 1 1 d . . . C4 C 0.30016(16) 0.2651(3) 1.02732(11) 0.0199(5) Uani 1 1 d . . . H4A H 0.3254 0.2267 1.0766 0.024 Uiso 1 1 calc R . . H4B H 0.2551 0.3752 1.0248 0.024 Uiso 1 1 calc R . . C5 C 0.34624(18) 0.4476(3) 0.91633(12) 0.0237(5) Uani 1 1 d . . . H5A H 0.3958 0.4622 0.8885 0.028 Uiso 1 1 calc R . . H5B H 0.2879 0.3700 0.8893 0.028 Uiso 1 1 calc R . . C6 C 0.30511(17) 0.6384(3) 0.92847(11) 0.0202(5) Uani 1 1 d . . . H6A H 0.3649 0.7192 0.9508 0.024 Uiso 1 1 calc R . . H6B H 0.2632 0.6243 0.9615 0.024 Uiso 1 1 calc R . . C7 C 0.11229(17) 0.6078(3) 0.82448(11) 0.0212(5) Uani 1 1 d . . . H7A H 0.0691 0.6474 0.7781 0.025 Uiso 1 1 calc R . . H7B H 0.1341 0.4777 0.8208 0.025 Uiso 1 1 calc R . . C8 C 0.04746(17) 0.6170(3) 0.87592(11) 0.0188(5) Uani 1 1 d . . . H8A H 0.0942 0.6088 0.9238 0.023 Uiso 1 1 calc R . . H8B H 0.0115 0.7385 0.8710 0.023 Uiso 1 1 calc R . . C9 C -0.12401(16) 0.4912(3) 0.81984(11) 0.0179(4) Uani 1 1 d . . . C10 C -0.23654(16) 0.2957(3) 0.86930(11) 0.0163(4) Uani 1 1 d . . . C11 C -0.32868(16) 0.1685(3) 0.84847(11) 0.0178(4) Uani 1 1 d . . . C12 C -0.40459(17) 0.1841(3) 0.88310(11) 0.0198(5) Uani 1 1 d . . . H12A H -0.3984 0.2763 0.9179 0.024 Uiso 1 1 calc R . . C13 C -0.48936(18) 0.0648(4) 0.86680(12) 0.0256(5) Uani 1 1 d . . . H13A H -0.5413 0.0759 0.8902 0.031 Uiso 1 1 calc R . . C14 C -0.49812(19) -0.0707(4) 0.81632(13) 0.0302(6) Uani 1 1 d . . . H14A H -0.5560 -0.1524 0.8053 0.036 Uiso 1 1 calc R . . C15 C -0.4227(2) -0.0870(4) 0.78190(13) 0.0311(6) Uani 1 1 d . . . H15A H -0.4289 -0.1801 0.7474 0.037 Uiso 1 1 calc R . . C16 C -0.33821(19) 0.0327(3) 0.79772(12) 0.0247(5) Uani 1 1 d . . . H16A H -0.2868 0.0219 0.7739 0.030 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 0.0177(3) 0.0165(3) 0.0269(3) 0.0061(2) 0.0049(2) -0.0013(2) O1 0.0186(7) 0.0223(9) 0.0177(8) -0.0039(7) 0.0052(6) -0.0021(7) N1 0.0172(9) 0.0134(9) 0.0187(9) 0.0011(7) 0.0057(7) -0.0002(7) C1 0.0170(10) 0.0146(11) 0.0212(11) -0.0005(9) 0.0055(8) 0.0015(9) N2 0.0198(9) 0.0221(10) 0.0144(9) -0.0037(8) 0.0034(7) -0.0032(8) S2 0.0153(3) 0.0275(3) 0.0296(3) 0.0040(3) 0.0067(2) -0.0001(2) C2 0.0149(10) 0.0169(11) 0.0198(11) 0.0023(9) 0.0050(8) 0.0014(9) S3 0.0220(3) 0.0236(3) 0.0181(3) 0.0021(2) 0.0075(2) -0.0047(2) C3 0.0165(10) 0.0171(12) 0.0241(11) -0.0005(9) 0.0037(9) 0.0012(9) S4 0.0301(3) 0.0248(3) 0.0343(3) 0.0124(3) 0.0038(3) 0.0035(3) C4 0.0174(10) 0.0223(12) 0.0207(11) 0.0005(9) 0.0069(9) 0.0004(9) C5 0.0234(11) 0.0284(14) 0.0211(11) -0.0004(10) 0.0093(9) -0.0008(10) C6 0.0202(11) 0.0246(13) 0.0157(10) -0.0009(9) 0.0049(8) -0.0018(9) C7 0.0201(11) 0.0275(13) 0.0168(10) -0.0015(9) 0.0066(9) -0.0055(10) C8 0.0208(11) 0.0174(11) 0.0192(11) 0.0000(9) 0.0075(9) -0.0034(9) C9 0.0204(11) 0.0171(11) 0.0176(10) 0.0000(9) 0.0075(8) 0.0017(9) C10 0.0145(10) 0.0158(11) 0.0179(10) -0.0001(9) 0.0038(8) 0.0040(9) C11 0.0172(10) 0.0187(12) 0.0161(10) 0.0028(9) 0.0026(8) 0.0005(9) C12 0.0194(10) 0.0206(12) 0.0181(10) 0.0002(9) 0.0032(8) 0.0025(9) C13 0.0192(11) 0.0279(14) 0.0293(12) 0.0063(11) 0.0063(9) 0.0008(10) C14 0.0241(12) 0.0297(14) 0.0314(13) 0.0015(11) -0.0008(10) -0.0093(11) C15 0.0391(14) 0.0262(14) 0.0254(12) -0.0080(11) 0.0048(11) -0.0085(12) C16 0.0297(12) 0.0237(13) 0.0214(11) -0.0029(10) 0.0087(10) -0.0023(10) 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 C2 1.809(2) . y S1 C3 1.812(2) . y S2 C4 1.816(2) . y S2 C5 1.820(2) . y S3 C6 1.818(2) . y S3 C7 1.815(2) . y S4 C9 1.667(2) . y O1 C10 1.218(3) . y N1 C1 1.480(3) . y N1 C8 1.472(3) . y N1 C9 1.342(3) . y N2 C9 1.411(3) . y N2 C10 1.379(3) . y C1 C2 1.528(3) . ? C3 C4 1.520(3) . ? C5 C6 1.525(3) . ? C7 C8 1.532(3) . ? C10 C11 1.501(3) . ? C11 C16 1.392(3) . ? C11 C12 1.394(3) . ? C12 C13 1.390(3) . ? C13 C14 1.387(4) . ? C14 C15 1.385(4) . ? C15 C16 1.389(3) . ? 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 C1 C2 S1 111.75(15) . . ? C2 S1 C3 101.16(10) . . y C3 C4 S2 113.28(15) . . ? C4 S2 C5 101.00(11) . . y C4 C3 S1 112.63(15) . . ? C5 C6 S3 115.29(16) . . ? C6 C5 S2 112.19(16) . . ? C7 S3 C6 102.75(11) . . y C8 C7 S3 111.86(15) . . ? C8 N1 C1 115.50(17) . . y C9 N1 C1 123.43(18) . . y C9 N1 C8 119.77(19) . . y C10 N2 C9 124.78(18) . . y C12 C11 C10 118.4(2) . . ? C13 C12 C11 120.1(2) . . ? C14 C13 C12 120.0(2) . . ? C14 C15 C16 120.1(2) . . ? C15 C16 C11 120.1(2) . . ? C15 C14 C13 120.2(2) . . ? C16 C11 C10 121.9(2) . . ? C16 C11 C12 119.6(2) . . ? N1 C1 C2 113.33(18) . . ? N1 C8 C7 112.45(18) . . ? N1 C9 N2 117.08(19) . . ? N1 C9 S4 124.87(17) . . ? N2 C9 S4 118.03(16) . . ? N2 C10 C11 114.70(18) . . ? O1 C10 N2 122.7(2) . . ? O1 C10 C11 122.56(19) . . ? 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 N2 H2A S3 0.88 2.54 3.331(2) 150 2_546 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.57 _refine_diff_density_min -0.48 _refine_diff_density_rms 0.06 #===END of CIF data_(3) #S2NOPH _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N2 O3 S2' _chemical_formula_sum 'C16 H22 N2 O3 S2' _chemical_formula_weight 354.48 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 'P 21/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 5.4621(4) _cell_length_b 19.6240(14) _cell_length_c 16.0384(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.023(2) _cell_angle_gamma 90.00 _cell_volume 1718.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6266 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.8 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17134 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.034 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.67 _reflns_number_total 4048 _reflns_number_gt 3044 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.01 (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXL97; PLATON (Spek, 2003)' _refine_special_details ; ? ; _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^)+(0.0424P)^2^+0.2091P] 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 4048 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags S1 S Uani 0.40793(8) 0.30683(2) 0.26192(3) 1.000 0.0296(1) . . S2 S Uani 0.48712(8) 0.56858(2) 0.37432(2) 1.000 0.0279(1) . . O1 O Uani 0.7485(2) 0.42431(5) 0.34838(6) 1.000 0.0252(3) . . O2 O Uani -0.0264(2) 0.46149(5) 0.10168(7) 1.000 0.0263(4) . . O3 O Uani -0.0268(2) 0.63735(6) 0.16927(7) 1.000 0.0286(4) . . N1 N Uani 0.2744(2) 0.50326(6) 0.18588(8) 1.000 0.0203(4) . . N2 N Uani 0.1278(2) 0.56671(6) 0.07033(8) 1.000 0.0222(4) . . C1 C Uani 0.2666(3) 0.44064(7) 0.23667(9) 1.000 0.0214(4) . . C2 C Uani 0.3990(3) 0.38180(8) 0.19559(10) 1.000 0.0244(5) . . C3 C Uani 0.7173(3) 0.30807(9) 0.30445(12) 1.000 0.0353(6) . . C4 C Uani 0.7682(4) 0.35551(9) 0.37614(11) 1.000 0.0361(6) . . C5 C Uani 0.8395(3) 0.47019(8) 0.40981(10) 1.000 0.0284(5) . . C6 C Uani 0.8061(3) 0.54234(8) 0.37941(11) 1.000 0.0280(5) . . C7 C Uani 0.4590(3) 0.60100(8) 0.26886(10) 1.000 0.0267(5) . . C8 C Uani 0.4836(3) 0.54911(8) 0.19874(10) 1.000 0.0233(5) . . C9 C Uani 0.1193(3) 0.50709(7) 0.12058(9) 1.000 0.0208(5) . . C10 C Uani 0.0360(3) 0.62779(8) 0.09743(10) 1.000 0.0226(5) . . C11 C Uani 0.0141(3) 0.68119(7) 0.03151(9) 1.000 0.0211(4) . . C12 C Uani -0.1855(3) 0.72509(8) 0.03249(11) 1.000 0.0284(5) . . C13 C Uani -0.2159(3) 0.77313(9) -0.03002(11) 1.000 0.0343(6) . . C14 C Uani -0.0442(3) 0.77892(8) -0.09180(11) 1.000 0.0327(5) . . C15 C Uani 0.1597(3) 0.73752(9) -0.09114(10) 1.000 0.0320(6) . . C16 C Uani 0.1867(3) 0.68758(8) -0.03033(10) 1.000 0.0273(5) . . H2A H Uiso 0.19330 0.56440 0.02070 1.000 0.0270 calc R H3A H Uiso 0.51130 0.57410 0.14610 1.000 0.0280 calc R H3B H Uiso 0.63100 0.52110 0.21030 1.000 0.0280 calc R H4A H Uiso 0.29740 0.62340 0.26260 1.000 0.0320 calc R H4B H Uiso 0.58540 0.63650 0.26150 1.000 0.0320 calc R H5A H Uiso 0.87690 0.54650 0.32320 1.000 0.0340 calc R H5B H Uiso 0.89760 0.57350 0.41720 1.000 0.0340 calc R H6A H Uiso 1.01540 0.46110 0.42100 1.000 0.0340 calc R H6B H Uiso 0.75040 0.46370 0.46240 1.000 0.0340 calc R H7A H Uiso 0.64950 0.34710 0.42090 1.000 0.0430 calc R H7B H Uiso 0.93490 0.34710 0.39910 1.000 0.0430 calc R H8A H Uiso 0.75940 0.26130 0.32270 1.000 0.0420 calc R H8B H Uiso 0.82920 0.32010 0.25890 1.000 0.0420 calc R H9A H Uiso 0.56840 0.39590 0.18300 1.000 0.0290 calc R H9B H Uiso 0.31490 0.37040 0.14220 1.000 0.0290 calc R H10A H Uiso 0.09380 0.42770 0.24540 1.000 0.0260 calc R H10B H Uiso 0.34310 0.44970 0.29200 1.000 0.0260 calc R H12A H Uiso -0.30090 0.72210 0.07600 1.000 0.0340 calc R H13A H Uiso -0.35500 0.80220 -0.03040 1.000 0.0410 calc R H14A H Uiso -0.06670 0.81160 -0.13500 1.000 0.0390 calc R H15A H Uiso 0.28140 0.74310 -0.13220 1.000 0.0380 calc R H16A H Uiso 0.32370 0.65780 -0.03110 1.000 0.0330 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 0.0305(2) 0.0228(2) 0.0353(2) 0.0066(2) -0.0037(2) -0.0018(2) S2 0.0285(2) 0.0319(2) 0.0233(2) -0.0063(2) -0.0010(2) -0.0012(2) O1 0.0281(6) 0.0257(6) 0.0215(6) 0.0008(4) -0.0054(5) -0.0012(5) O2 0.0308(7) 0.0242(6) 0.0237(6) -0.0008(4) -0.0076(5) -0.0060(5) O3 0.0334(7) 0.0287(6) 0.0238(6) -0.0005(5) 0.0017(5) 0.0040(5) N1 0.0225(7) 0.0197(6) 0.0186(6) 0.0001(5) -0.0032(5) -0.0024(5) N2 0.0292(7) 0.0208(7) 0.0165(6) -0.0009(5) -0.0010(5) 0.0004(5) C1 0.0246(8) 0.0210(8) 0.0186(7) 0.0016(6) -0.0014(6) -0.0014(6) C2 0.0279(9) 0.0232(8) 0.0221(8) 0.0028(6) -0.0005(7) 0.0014(6) C3 0.0380(11) 0.0262(9) 0.0412(10) 0.0024(8) -0.0130(8) 0.0059(8) C4 0.0474(12) 0.0294(9) 0.0312(10) 0.0057(7) -0.0114(8) 0.0030(8) C5 0.0305(9) 0.0337(9) 0.0207(8) -0.0014(7) -0.0066(7) -0.0011(7) C6 0.0269(9) 0.0319(9) 0.0250(8) -0.0016(7) -0.0072(7) -0.0041(7) C7 0.0290(9) 0.0227(8) 0.0280(9) -0.0004(6) -0.0071(7) -0.0031(6) C8 0.0225(8) 0.0253(8) 0.0220(8) 0.0018(6) -0.0029(6) -0.0052(6) C9 0.0239(8) 0.0199(8) 0.0186(8) -0.0026(6) -0.0005(6) 0.0016(6) C10 0.0202(8) 0.0219(8) 0.0256(8) -0.0016(6) -0.0046(7) -0.0022(6) C11 0.0240(8) 0.0174(7) 0.0217(8) -0.0027(6) -0.0051(6) -0.0016(6) C12 0.0272(9) 0.0269(9) 0.0311(9) -0.0022(7) -0.0014(7) 0.0016(7) C13 0.0368(10) 0.0245(9) 0.0412(11) 0.0013(7) -0.0102(8) 0.0053(7) C14 0.0481(11) 0.0219(8) 0.0277(9) 0.0028(7) -0.0093(8) -0.0026(8) C15 0.0423(11) 0.0285(9) 0.0253(9) 0.0016(7) 0.0014(8) -0.0053(8) C16 0.0286(9) 0.0240(8) 0.0292(9) -0.0013(7) -0.0007(7) 0.0008(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.8157(16) . . yes S1 C3 1.8111(17) . . yes S2 C6 1.8172(17) . . yes S2 C7 1.8111(16) . . yes O1 C4 1.425(2) . . yes O1 C5 1.4181(19) . . yes O2 C9 1.2318(18) . . yes O3 C10 1.223(2) . . yes N1 C1 1.4754(19) . . yes N1 C8 1.466(2) . . yes N1 C9 1.3374(19) . . yes N2 C9 1.4219(19) . . yes N2 C10 1.373(2) . . yes N2 H2A 0.8800 . . no C1 C2 1.519(2) . . no C3 C4 1.502(3) . . no C5 C6 1.508(2) . . no C7 C8 1.525(2) . . no C10 C11 1.492(2) . . no C11 C16 1.386(2) . . no C11 C12 1.390(2) . . no C12 C13 1.384(2) . . no C13 C14 1.381(2) . . no C14 C15 1.378(2) . . no C15 C16 1.389(2) . . no C1 H10A 0.9900 . . no C1 H10B 0.9900 . . no C2 H9A 0.9900 . . no C2 H9B 0.9900 . . no C3 H8A 0.9900 . . no C3 H8B 0.9900 . . no C4 H7A 0.9900 . . no C4 H7B 0.9900 . . no C5 H6A 0.9900 . . no C5 H6B 0.9900 . . no C6 H5A 0.9900 . . no C6 H5B 0.9900 . . no C7 H4A 0.9900 . . no C7 H4B 0.9900 . . no C8 H3A 0.9900 . . no C8 H3B 0.9900 . . no C12 H12A 0.9500 . . no C13 H13A 0.9500 . . no C14 H14A 0.9500 . . no C15 H15A 0.9500 . . no C16 H16A 0.9500 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C3 103.00(8) . . . yes C6 S2 C7 101.93(8) . . . yes C4 O1 C5 111.15(12) . . . yes C1 N1 C8 117.62(12) . . . yes C1 N1 C9 117.07(12) . . . yes C8 N1 C9 123.84(13) . . . yes C9 N2 C10 121.54(13) . . . yes C9 N2 H2A 119.00 . . . no C10 N2 H2A 119.00 . . . no N1 C1 C2 112.02(12) . . . yes S1 C2 C1 111.70(11) . . . yes S1 C3 C4 117.10(13) . . . yes O1 C4 C3 109.65(14) . . . yes O1 C5 C6 109.43(13) . . . yes S2 C6 C5 113.02(11) . . . yes S2 C7 C8 116.56(11) . . . yes N1 C8 C7 115.78(13) . . . yes N1 C9 N2 117.61(13) . . . yes O2 C9 N2 119.06(13) . . . yes O2 C9 N1 123.32(13) . . . yes O3 C10 N2 122.86(14) . . . yes O3 C10 C11 122.67(14) . . . yes N2 C10 C11 114.46(13) . . . yes C10 C11 C12 118.71(14) . . . no C12 C11 C16 119.71(14) . . . no C10 C11 C16 121.58(14) . . . no C11 C12 C13 119.87(15) . . . no C12 C13 C14 120.10(15) . . . no C13 C14 C15 120.33(16) . . . no C14 C15 C16 119.80(15) . . . no C11 C16 C15 120.09(15) . . . no N1 C1 H10A 109.00 . . . no N1 C1 H10B 109.00 . . . no C2 C1 H10A 109.00 . . . no C2 C1 H10B 109.00 . . . no H10A C1 H10B 108.00 . . . no S1 C2 H9A 109.00 . . . no S1 C2 H9B 109.00 . . . no C1 C2 H9A 109.00 . . . no C1 C2 H9B 109.00 . . . no H9A C2 H9B 108.00 . . . no S1 C3 H8A 108.00 . . . no S1 C3 H8B 108.00 . . . no C4 C3 H8A 108.00 . . . no C4 C3 H8B 108.00 . . . no H8A C3 H8B 107.00 . . . no O1 C4 H7A 110.00 . . . no O1 C4 H7B 110.00 . . . no C3 C4 H7A 110.00 . . . no C3 C4 H7B 110.00 . . . no H7A C4 H7B 108.00 . . . no O1 C5 H6A 110.00 . . . no O1 C5 H6B 110.00 . . . no C6 C5 H6A 110.00 . . . no C6 C5 H6B 110.00 . . . no H6A C5 H6B 108.00 . . . no S2 C6 H5A 109.00 . . . no S2 C6 H5B 109.00 . . . no C5 C6 H5A 109.00 . . . no C5 C6 H5B 109.00 . . . no H5A C6 H5B 108.00 . . . no S2 C7 H4A 108.00 . . . no S2 C7 H4B 108.00 . . . no C8 C7 H4A 108.00 . . . no C8 C7 H4B 108.00 . . . no H4A C7 H4B 107.00 . . . no N1 C8 H3A 108.00 . . . no N1 C8 H3B 108.00 . . . no C7 C8 H3A 108.00 . . . no C7 C8 H3B 108.00 . . . no H3A C8 H3B 107.00 . . . no C11 C12 H12A 120.00 . . . no C13 C12 H12A 120.00 . . . no C12 C13 H13A 120.00 . . . no C14 C13 H13A 120.00 . . . no C13 C14 H14A 120.00 . . . no C15 C14 H14A 120.00 . . . no C14 C15 H15A 120.00 . . . no C16 C15 H15A 120.00 . . . no C11 C16 H16A 120.00 . . . no C15 C16 H16A 120.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 S1 C2 C1 -102.21(12) . . . . no C2 S1 C3 C4 79.81(15) . . . . no C7 S2 C6 C5 -128.37(12) . . . . no C6 S2 C7 C8 66.74(13) . . . . no C5 O1 C4 C3 -168.99(14) . . . . no C4 O1 C5 C6 -177.76(14) . . . . no C8 N1 C1 C2 -88.45(16) . . . . no C9 N1 C1 C2 78.27(17) . . . . no C1 N1 C8 C7 -85.95(16) . . . . no C9 N1 C8 C7 108.31(16) . . . . no C1 N1 C9 O2 0.1(2) . . . . no C1 N1 C9 N2 -178.99(12) . . . . no C8 N1 C9 O2 165.87(14) . . . . no C8 N1 C9 N2 -13.2(2) . . . . no C10 N2 C9 O2 107.18(17) . . . . no C10 N2 C9 N1 -73.74(18) . . . . no C9 N2 C10 O3 10.3(2) . . . . no C9 N2 C10 C11 -168.43(13) . . . . no N1 C1 C2 S1 175.78(10) . . . . no S1 C3 C4 O1 -67.35(19) . . . . no O1 C5 C6 S2 69.41(15) . . . . no S2 C7 C8 N1 73.72(16) . . . . no O3 C10 C11 C12 -35.9(2) . . . . no O3 C10 C11 C16 144.47(16) . . . . no N2 C10 C11 C12 142.91(15) . . . . no N2 C10 C11 C16 -36.8(2) . . . . no C10 C11 C12 C13 -177.17(15) . . . . no C16 C11 C12 C13 2.5(2) . . . . no C10 C11 C16 C15 179.49(15) . . . . no C12 C11 C16 C15 -0.2(2) . . . . no C11 C12 C13 C14 -2.1(3) . . . . no C12 C13 C14 C15 -0.7(3) . . . . no C13 C14 C15 C16 3.1(3) . . . . no C14 C15 C16 C11 -2.6(2) . . . . no _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.52 _refine_diff_density_min -0.61 _refine_diff_density_rms 0.05 #===END of CIF data_(12) #S2NOTB _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H29 N3 O3 S2' _chemical_formula_sum 'C15 H29 N3 O3 S2' _chemical_formula_weight 363.53 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 'P 21/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 12.5943(8) _cell_length_b 14.8366(10) _cell_length_c 10.1311(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.462(1) _cell_angle_gamma 90.00 _cell_volume 1867.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3561 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.34 _exptl_crystal_description 'rectangular plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11916 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.83 _reflns_number_total 4539 _reflns_number_gt 3131 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; ? ; _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^)+(0.0483P)^2^] 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 ? _refine_ls_extinction_coef ? _refine_ls_number_reflns 4368 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _refine_ls_shift/su_max 0.000 _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 S1 S 0.30290(3) 0.17142(3) -0.15229(4) 0.02855(12) Uani 1 1 d . . . O1 O 0.24745(9) 0.04134(8) 0.08370(11) 0.0279(3) Uani 1 1 d . . . N1 N 0.53808(10) 0.14597(9) 0.18500(12) 0.0227(3) Uani 1 1 d . . . C1 C 0.48042(13) 0.13811(11) 0.04695(15) 0.0239(4) Uani 1 1 d . . . H1A H 0.4599 0.0742 0.0301 0.029 Uiso 1 1 calc R . . H1B H 0.5308 0.1542 -0.0147 0.029 Uiso 1 1 calc R . . S2 S 0.36356(4) -0.01978(3) 0.39364(4) 0.03047(12) Uani 1 1 d . . . O2 O 0.70182(9) 0.30512(8) 0.39376(12) 0.0309(3) Uani 1 1 d . . . N2 N 0.73661(11) 0.16199(9) 0.32964(13) 0.0272(3) Uani 1 1 d . . . H2A H 0.7089 0.1188 0.2750 0.033 Uiso 1 1 calc R . . C2 C 0.37882(13) 0.19628(11) 0.01177(15) 0.0250(4) Uani 1 1 d . . . H2B H 0.3999 0.2606 0.0150 0.030 Uiso 1 1 calc R . . H2C H 0.3320 0.1865 0.0800 0.030 Uiso 1 1 calc R . . N3 N 0.88412(10) 0.20996(9) 0.48127(13) 0.0251(3) Uani 1 1 d . . . H3C H 0.8498 0.2618 0.4736 0.030 Uiso 1 1 calc R . . O3 O 0.87104(10) 0.06400(8) 0.40733(13) 0.0375(3) Uani 1 1 d . . . C3 C 0.27305(14) 0.05232(11) -0.14596(16) 0.0275(4) Uani 1 1 d . . . H3A H 0.2405 0.0329 -0.2372 0.033 Uiso 1 1 calc R . . H3B H 0.3421 0.0196 -0.1222 0.033 Uiso 1 1 calc R . . C4 C 0.19927(14) 0.02239(12) -0.05045(16) 0.0298(4) Uani 1 1 d . . . H4A H 0.1296 0.0544 -0.0716 0.036 Uiso 1 1 calc R . . H4B H 0.1853 -0.0431 -0.0609 0.036 Uiso 1 1 calc R . . C5 C 0.19042(13) -0.00040(11) 0.17806(17) 0.0286(4) Uani 1 1 d . . . H5A H 0.1965 -0.0668 0.1722 0.034 Uiso 1 1 calc R . . H5B H 0.1132 0.0159 0.1577 0.034 Uiso 1 1 calc R . . C6 C 0.23723(13) 0.03079(12) 0.31742(16) 0.0291(4) Uani 1 1 d . . . H6A H 0.1834 0.0191 0.3765 0.035 Uiso 1 1 calc R . . H6B H 0.2477 0.0969 0.3147 0.035 Uiso 1 1 calc R . . C7 C 0.45527(13) 0.01317(11) 0.28210(16) 0.0252(4) Uani 1 1 d . . . H7A H 0.5244 -0.0190 0.3076 0.030 Uiso 1 1 calc R . . H7B H 0.4246 -0.0046 0.1894 0.030 Uiso 1 1 calc R . . C8 C 0.47566(13) 0.11423(10) 0.28702(15) 0.0234(4) Uani 1 1 d . . . H8A H 0.4056 0.1460 0.2744 0.028 Uiso 1 1 calc R . . H8B H 0.5149 0.1303 0.3768 0.028 Uiso 1 1 calc R . . C9 C 0.57750(13) 0.23730(11) 0.21670(16) 0.0262(4) Uani 1 1 d . . . H9A H 0.5200 0.2731 0.2477 0.031 Uiso 1 1 calc R . . H9B H 0.5945 0.2661 0.1345 0.031 Uiso 1 1 calc R . . C10 C 0.67698(13) 0.23877(11) 0.32359(16) 0.0243(4) Uani 1 1 d . . . C11 C 0.83675(13) 0.14069(11) 0.41054(16) 0.0262(4) Uani 1 1 d . . . C12 C 0.98919(13) 0.20718(11) 0.57129(15) 0.0242(4) Uani 1 1 d . . . C13 C 1.07773(14) 0.17356(13) 0.49695(18) 0.0362(4) Uani 1 1 d . . . H13A H 1.0817 0.2129 0.4202 0.054 Uiso 1 1 calc R . . H13B H 1.0613 0.1119 0.4654 0.054 Uiso 1 1 calc R . . H13C H 1.1469 0.1743 0.5575 0.054 Uiso 1 1 calc R . . C14 C 0.98197(15) 0.14668(12) 0.69095(17) 0.0341(4) Uani 1 1 d . . . H14A H 0.9250 0.1688 0.7379 0.051 Uiso 1 1 calc R . . H14B H 1.0509 0.1474 0.7520 0.051 Uiso 1 1 calc R . . H14C H 0.9653 0.0849 0.6599 0.051 Uiso 1 1 calc R . . C15 C 1.01214(14) 0.30414(12) 0.61659(17) 0.0335(4) Uani 1 1 d . . . H15A H 0.9552 0.3253 0.6642 0.050 Uiso 1 1 calc R . . H15B H 1.0144 0.3425 0.5383 0.050 Uiso 1 1 calc R . . H15C H 1.0816 0.3070 0.6764 0.050 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 0.0295(2) 0.0316(2) 0.0218(2) 0.00409(17) -0.00409(17) -0.00353(18) O1 0.0270(7) 0.0316(7) 0.0242(6) 0.0046(5) 0.0010(5) -0.0061(5) N1 0.0201(7) 0.0263(7) 0.0204(7) -0.0004(6) -0.0010(5) -0.0027(6) C1 0.0221(9) 0.0295(9) 0.0192(8) -0.0008(7) 0.0010(7) -0.0027(7) S2 0.0320(3) 0.0334(3) 0.0255(2) 0.00845(19) 0.00324(18) 0.00075(19) O2 0.0278(7) 0.0266(7) 0.0359(7) -0.0061(5) -0.0016(5) -0.0011(5) N2 0.0240(8) 0.0265(8) 0.0278(8) -0.0072(6) -0.0050(6) -0.0016(6) C2 0.0262(9) 0.0249(9) 0.0217(8) 0.0011(7) -0.0024(7) -0.0028(7) N3 0.0223(8) 0.0233(7) 0.0271(7) -0.0015(6) -0.0036(6) 0.0006(6) O3 0.0333(7) 0.0285(7) 0.0451(8) -0.0084(6) -0.0098(6) 0.0042(5) C3 0.0274(10) 0.0290(9) 0.0238(8) -0.0051(7) -0.0025(7) -0.0006(7) C4 0.0278(10) 0.0301(9) 0.0285(9) 0.0013(8) -0.0041(7) -0.0052(7) C5 0.0227(9) 0.0283(9) 0.0349(10) 0.0063(7) 0.0047(7) -0.0005(7) C6 0.0256(9) 0.0312(10) 0.0321(9) 0.0053(8) 0.0094(8) 0.0021(7) C7 0.0238(9) 0.0267(9) 0.0243(8) 0.0016(7) 0.0018(7) 0.0024(7) C8 0.0246(9) 0.0255(9) 0.0191(8) -0.0014(7) 0.0009(7) 0.0003(7) C9 0.0226(9) 0.0265(9) 0.0278(9) 0.0027(7) -0.0009(7) -0.0031(7) C10 0.0215(9) 0.0260(9) 0.0252(8) 0.0009(7) 0.0031(7) -0.0030(7) C11 0.0235(9) 0.0285(9) 0.0258(9) -0.0014(7) 0.0014(7) -0.0004(7) C12 0.0209(9) 0.0286(9) 0.0214(8) 0.0009(7) -0.0012(7) -0.0035(7) C13 0.0247(10) 0.0525(12) 0.0306(10) -0.0009(9) 0.0023(8) 0.0014(8) C14 0.0332(10) 0.0397(11) 0.0277(9) 0.0059(8) -0.0008(8) -0.0070(8) C15 0.0329(11) 0.0338(10) 0.0303(10) -0.0004(8) -0.0055(8) -0.0074(8) 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 C1 1.4707(19) . ? N1 C8 1.4748(19) . ? N1 C9 1.461(2) . ? N2 C10 1.360(2) . ? N2 C11 1.422(2) . ? N3 C11 1.336(2) . ? N3 C12 1.4790(19) . ? O1 C4 1.4223(19) . ? O1 C5 1.4279(19) . ? O2 C10 1.2243(19) . ? O3 C11 1.219(2) . ? S1 C2 1.8138(15) . ? S1 C3 1.8099(17) . ? S2 C6 1.8129(17) . ? S2 C7 1.8110(16) . ? C1 C2 1.536(2) . ? C3 C4 1.514(2) . ? C5 C6 1.510(2) . ? C7 C8 1.521(2) . ? C9 C10 1.515(2) . ? C12 C13 1.528(2) . ? C12 C14 1.523(2) . ? C12 C15 1.523(2) . ? 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 C1 C2 S1 113.07(11) . . ? C1 N1 C8 113.85(12) . . ? C3 S1 C2 104.32(8) . . ? C4 O1 C5 111.81(12) . . ? C4 C3 S1 117.50(12) . . ? C5 C6 S2 116.85(12) . . ? C7 S2 C6 103.15(8) . . ? C8 C7 S2 111.55(11) . . ? C9 N1 C1 112.30(12) . . ? C9 N1 C8 110.07(12) . . ? C10 N2 C11 130.00(14) . . ? C11 N3 C12 125.77(14) . . ? C14 C12 C13 110.11(15) . . ? C14 C12 C15 110.48(14) . . ? C15 C12 C13 109.82(14) . . ? N1 C1 C2 116.00(13) . . ? N1 C8 C7 113.48(12) . . ? N1 C9 C10 112.44(13) . . ? N2 C10 C9 113.93(14) . . ? N3 C11 N2 114.43(14) . . ? N3 C12 C13 110.89(13) . . ? N3 C12 C14 110.05(13) . . ? N3 C12 C15 105.40(13) . . ? O1 C4 C3 110.03(13) . . ? O1 C5 C6 109.33(13) . . ? O2 C10 N2 124.10(15) . . ? O2 C10 C9 121.93(15) . . ? O3 C11 N2 118.45(15) . . ? O3 C11 N3 127.10(16) . . ? 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 N2 H2A N1 0.88 2.23 2.6927(18) 112 . N3 H3C O2 0.88 2.01 2.7168(18) 136 . _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.346 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.050 #===END of CIF data_(15) #S2N2TB _refine_special_details ; The dichloromethane solvent was modelled over two sites which were found to be occupied in the ratio 80:20. A difference electron density peak of 1.46 e/A^3^ remains in the solvent region but this cannot sensibly be incorporated into the disorder model. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H46 N6 O5 S2, C H2 Cl2' _chemical_formula_sum 'C25 H48 Cl2 N6 O5 S2' _chemical_formula_weight 647.71 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' 0.00 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3080(7) _cell_length_b 10.3129(7) _cell_length_c 16.9116(11) _cell_angle_alpha 88.351(1) _cell_angle_beta 84.537(1) _cell_angle_gamma 72.061(1) _cell_volume 1702.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4754 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.39 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.354 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17399 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.015 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6625 _reflns_number_gt 5620 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.01 (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2003)' _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^)+(0.1041P)^2^+1.4976P] 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 6625 _refine_ls_number_parameters 369 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.180 _refine_ls_wR_factor_gt 0.171 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.048 _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 S1 S 0.70726(9) 0.57487(7) 0.39726(4) 0.0476(2) Uani 1 1 d U . . N1 N 0.6780(2) 0.68143(19) 0.75856(11) 0.0277(4) Uani 1 1 d U . . O1 O 0.7022(3) 0.8624(2) 0.47095(11) 0.0520(5) Uani 1 1 d U . . C1 C 0.6811(3) 0.8191(2) 0.73676(14) 0.0325(5) Uani 1 1 d U . . H1A H 0.7337 0.8503 0.7741 0.039 Uiso 1 1 calc R . . H1B H 0.5867 0.8828 0.7406 0.039 Uiso 1 1 calc R . . S2 S 0.75619(9) 0.99055(7) 0.63144(4) 0.0461(2) Uani 1 1 d U . . O2 O 0.5081(2) 0.86010(18) 0.89027(12) 0.0464(5) Uani 1 1 d U . . N2 N 0.7375(2) 0.4698(2) 0.63259(11) 0.0298(4) Uani 1 1 d U . . C2 C 0.7470(3) 0.8201(3) 0.65262(15) 0.0397(6) Uani 1 1 d U . . H2A H 0.6917 0.7947 0.6145 0.048 Uiso 1 1 calc R . . H2B H 0.8400 0.7536 0.6476 0.048 Uiso 1 1 calc R . . O3 O 0.3738(2) 0.61806(18) 1.05722(11) 0.0405(4) Uani 1 1 d U . . N3 N 0.5064(2) 0.6606(2) 0.95114(11) 0.0291(4) Uani 1 1 d U . . H3N H 0.5455 0.5719 0.9478 0.035 Uiso 1 1 calc R . . C3 C 0.8435(4) 0.9678(4) 0.53233(19) 0.0597(9) Uani 1 1 d U . . H3A H 0.8899 1.0386 0.5232 0.072 Uiso 1 1 calc R . . H3B H 0.9155 0.8782 0.5301 0.072 Uiso 1 1 calc R . . O4 O 1.0277(2) 0.21439(18) 0.70761(12) 0.0422(4) Uani 1 1 d U . . N4 N 0.3399(2) 0.8379(2) 1.01931(11) 0.0285(4) Uani 1 1 d U . . H4N H 0.3677 0.8919 0.9852 0.034 Uiso 1 1 calc R . . C4 C 0.7549(5) 0.9744(3) 0.46531(18) 0.0632(10) Uani 1 1 d U . . H4A H 0.6785 1.0608 0.4684 0.076 Uiso 1 1 calc R . . H4B H 0.8097 0.9717 0.4137 0.076 Uiso 1 1 calc R . . N5 N 0.9441(2) 0.4456(2) 0.72695(12) 0.0320(4) Uani 1 1 d U . . H5N H 0.8790 0.5179 0.7130 0.038 Uiso 1 1 calc R . . O5 O 1.0123(2) 0.58755(19) 0.80205(12) 0.0415(4) Uani 1 1 d U . . C5 C 0.6253(4) 0.8601(3) 0.40583(19) 0.0552(8) Uani 1 1 d U . . H5A H 0.6831 0.8564 0.3552 0.066 Uiso 1 1 calc R . . H5B H 0.5459 0.9439 0.4059 0.066 Uiso 1 1 calc R . . N6 N 1.1282(2) 0.3591(2) 0.80320(12) 0.0348(5) Uani 1 1 d U . . H6N H 1.1309 0.2802 0.7834 0.042 Uiso 1 1 calc R . . C6 C 0.5766(4) 0.7367(3) 0.41347(19) 0.0517(7) Uani 1 1 d U . . H6A H 0.5077 0.7455 0.3751 0.062 Uiso 1 1 calc R . . H6B H 0.5300 0.7365 0.4674 0.062 Uiso 1 1 calc R . . C7 C 0.7767(3) 0.5396(3) 0.49322(15) 0.0379(6) Uani 1 1 d U . . H7A H 0.8657 0.4665 0.4869 0.045 Uiso 1 1 calc R . . H7B H 0.7937 0.6223 0.5122 0.045 Uiso 1 1 calc R . . C8 C 0.6818(3) 0.4961(3) 0.55511(14) 0.0339(5) Uani 1 1 d U . . H8A H 0.5924 0.5685 0.5609 0.041 Uiso 1 1 calc R . . H8B H 0.6659 0.4125 0.5366 0.041 Uiso 1 1 calc R . . C9 C 0.6279(3) 0.4900(3) 0.69815(14) 0.0326(5) Uani 1 1 d U . . H9A H 0.6642 0.4332 0.7441 0.039 Uiso 1 1 calc R . . H9B H 0.5524 0.4602 0.6809 0.039 Uiso 1 1 calc R . . C10 C 0.5729(2) 0.6387(2) 0.72329(14) 0.0307(5) Uani 1 1 d U . . H10A H 0.5432 0.6963 0.6765 0.037 Uiso 1 1 calc R . . H10B H 0.4922 0.6516 0.7624 0.037 Uiso 1 1 calc R . . C11 C 0.6815(3) 0.6528(2) 0.84336(13) 0.0312(5) Uani 1 1 d U . . H11A H 0.7637 0.6695 0.8611 0.037 Uiso 1 1 calc R . . H11B H 0.6916 0.5549 0.8518 0.037 Uiso 1 1 calc R . . C12 C 0.5558(3) 0.7365(2) 0.89592(13) 0.0313(5) Uani 1 1 d U . . C13 C 0.4013(2) 0.7052(2) 1.01274(13) 0.0286(5) Uani 1 1 d U . . C14 C 0.2270(2) 0.9015(2) 1.08062(14) 0.0303(5) Uani 1 1 d U . . C15 C 0.2772(3) 0.8724(3) 1.16342(15) 0.0411(6) Uani 1 1 d U . . H15A H 0.3544 0.9078 1.1672 0.062 Uiso 1 1 calc R . . H15B H 0.3067 0.7738 1.1728 0.062 Uiso 1 1 calc R . . H15C H 0.2027 0.9170 1.2034 0.062 Uiso 1 1 calc R . . C16 C 0.1878(3) 1.0539(3) 1.06388(16) 0.0407(6) Uani 1 1 d U . . H16A H 0.1557 1.0719 1.0108 0.061 Uiso 1 1 calc R . . H16B H 0.2679 1.0853 1.0666 0.061 Uiso 1 1 calc R . . H16C H 0.1147 1.1026 1.1035 0.061 Uiso 1 1 calc R . . C17 C 0.1067(3) 0.8480(3) 1.0724(2) 0.0471(7) Uani 1 1 d U . . H17A H 0.0765 0.8679 1.0190 0.071 Uiso 1 1 calc R . . H17B H 0.0311 0.8924 1.1119 0.071 Uiso 1 1 calc R . . H17C H 0.1351 0.7493 1.0812 0.071 Uiso 1 1 calc R . . C18 C 0.8403(3) 0.3370(3) 0.63577(15) 0.0359(5) Uani 1 1 d U . . H18A H 0.8883 0.3144 0.5820 0.043 Uiso 1 1 calc R . . H18B H 0.7932 0.2680 0.6499 0.043 Uiso 1 1 calc R . . C19 C 0.9467(3) 0.3259(2) 0.69423(14) 0.0327(5) Uani 1 1 d U . . C20 C 1.0320(2) 0.4700(3) 0.78070(14) 0.0323(5) Uani 1 1 d U . . C21 C 1.2305(3) 0.3588(3) 0.85886(15) 0.0390(6) Uani 1 1 d U . . C22 C 1.3183(3) 0.2101(4) 0.8642(2) 0.0550(8) Uani 1 1 d U . . H22A H 1.3648 0.1788 0.8117 0.083 Uiso 1 1 calc R . . H22B H 1.2598 0.1539 0.8821 0.083 Uiso 1 1 calc R . . H22C H 1.3865 0.2021 0.9021 0.083 Uiso 1 1 calc R . . C23 C 1.3174(3) 0.4480(4) 0.8272(2) 0.0557(8) Uani 1 1 d U . . H23A H 1.2592 0.5428 0.8243 0.084 Uiso 1 1 calc R . . H23B H 1.3603 0.4166 0.7740 0.084 Uiso 1 1 calc R . . H23C H 1.3886 0.4418 0.8628 0.084 Uiso 1 1 calc R . . C24 C 1.1575(3) 0.4086(4) 0.94016(17) 0.0533(8) Uani 1 1 d U . . H24A H 1.1014 0.5040 0.9363 0.080 Uiso 1 1 calc R . . H24B H 1.2255 0.4009 0.9782 0.080 Uiso 1 1 calc R . . H24C H 1.0987 0.3528 0.9582 0.080 Uiso 1 1 calc R . . C1A C 0.0948(4) 0.8616(4) 0.7414(2) 0.0996(10) Uani 0.80 1 d PDU A 1 Cl1A Cl 0.17190(17) 0.76342(12) 0.65409(9) 0.0814(4) Uani 0.80 1 d PDU A 1 Cl2A Cl 0.21262(11) 0.87964(13) 0.80683(11) 0.0888(5) Uani 0.80 1 d PDU A 1 Cl1' Cl 0.1101(3) 0.7662(3) 0.60451(17) 0.0297(5) Uiso 0.20 1 d PDU B 2 C1' C 0.2305(13) 0.794(5) 0.6664(14) 0.17(2) Uiso 0.20 1 d PDU B 2 Cl2' Cl 0.0948(4) 0.8616(4) 0.7414(2) 0.0996(10) Uani 0.20 1 d PDU 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 S1 0.0696(5) 0.0405(4) 0.0293(3) -0.0045(3) -0.0069(3) -0.0110(3) N1 0.0322(10) 0.0269(10) 0.0249(9) -0.0023(7) 0.0007(7) -0.0113(8) O1 0.0888(16) 0.0426(11) 0.0319(10) 0.0005(8) 0.0000(10) -0.0325(11) C1 0.0406(13) 0.0284(12) 0.0299(12) -0.0038(9) 0.0020(10) -0.0137(10) S2 0.0735(5) 0.0381(4) 0.0355(4) -0.0043(3) 0.0064(3) -0.0330(4) O2 0.0581(12) 0.0276(9) 0.0427(10) 0.0017(8) 0.0183(9) -0.0043(8) N2 0.0325(10) 0.0290(10) 0.0284(10) -0.0034(8) -0.0024(8) -0.0098(8) C2 0.0581(17) 0.0327(13) 0.0338(13) -0.0045(10) 0.0087(11) -0.0251(12) O3 0.0473(11) 0.0263(9) 0.0420(10) -0.0016(7) 0.0153(8) -0.0082(8) N3 0.0341(10) 0.0233(9) 0.0281(9) -0.0031(7) 0.0030(8) -0.0077(8) C3 0.086(2) 0.0582(19) 0.0484(17) -0.0065(14) 0.0227(16) -0.0494(19) O4 0.0421(10) 0.0294(9) 0.0500(11) -0.0022(8) -0.0072(8) -0.0022(8) N4 0.0322(10) 0.0257(9) 0.0262(9) -0.0025(7) 0.0019(8) -0.0080(8) C4 0.116(3) 0.0478(18) 0.0346(15) -0.0021(12) 0.0160(16) -0.044(2) N5 0.0305(10) 0.0292(10) 0.0363(11) -0.0002(8) -0.0063(8) -0.0084(8) O5 0.0444(11) 0.0370(10) 0.0471(11) -0.0024(8) -0.0112(8) -0.0164(8) C5 0.084(2) 0.0407(16) 0.0396(15) 0.0037(12) -0.0090(15) -0.0158(15) N6 0.0304(10) 0.0400(12) 0.0337(11) 0.0016(9) -0.0045(8) -0.0103(9) C6 0.065(2) 0.0407(15) 0.0475(16) -0.0012(12) -0.0149(14) -0.0110(14) C7 0.0404(14) 0.0415(14) 0.0325(12) -0.0032(10) -0.0030(10) -0.0136(11) C8 0.0342(13) 0.0374(13) 0.0314(12) -0.0040(10) -0.0054(10) -0.0121(10) C9 0.0365(13) 0.0333(12) 0.0313(12) -0.0020(9) 0.0015(10) -0.0170(10) C10 0.0275(11) 0.0333(12) 0.0322(12) -0.0025(9) 0.0018(9) -0.0119(10) C11 0.0356(13) 0.0278(11) 0.0267(11) -0.0017(9) 0.0023(9) -0.0060(10) C12 0.0368(13) 0.0293(12) 0.0258(11) -0.0026(9) 0.0010(9) -0.0084(10) C13 0.0295(11) 0.0276(11) 0.0279(11) -0.0046(9) -0.0001(9) -0.0080(9) C14 0.0288(11) 0.0281(11) 0.0299(11) -0.0053(9) 0.0021(9) -0.0037(9) C15 0.0495(16) 0.0380(14) 0.0290(12) -0.0051(10) 0.0015(11) -0.0043(12) C16 0.0428(15) 0.0304(13) 0.0407(14) -0.0026(10) 0.0027(11) -0.0007(11) C17 0.0316(13) 0.0477(16) 0.0606(18) -0.0105(13) 0.0046(12) -0.0119(12) C18 0.0409(14) 0.0291(12) 0.0367(13) -0.0066(10) -0.0052(10) -0.0081(10) C19 0.0326(12) 0.0312(12) 0.0327(12) -0.0016(9) 0.0005(9) -0.0082(10) C20 0.0314(12) 0.0370(13) 0.0306(12) 0.0019(10) -0.0015(9) -0.0142(10) C21 0.0322(13) 0.0553(16) 0.0293(12) 0.0038(11) -0.0035(10) -0.0132(12) C22 0.0415(16) 0.064(2) 0.0509(17) 0.0025(15) -0.0134(13) -0.0018(14) C23 0.0449(16) 0.085(2) 0.0491(17) 0.0122(16) -0.0128(13) -0.0353(17) C24 0.0476(17) 0.075(2) 0.0313(14) -0.0008(13) -0.0013(12) -0.0098(15) C1A 0.095(2) 0.088(2) 0.109(2) -0.0161(17) 0.0120(18) -0.0234(17) Cl1A 0.0941(10) 0.0437(6) 0.0965(10) -0.0096(6) 0.0385(8) -0.0197(6) Cl2A 0.0411(6) 0.0544(6) 0.1615(14) -0.0472(8) -0.0194(7) 0.0064(5) Cl2' 0.095(2) 0.088(2) 0.109(2) -0.0161(17) 0.0120(18) -0.0234(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1' C1' 1.79(2) . . yes Cl1A C1A 1.790(4) . . yes Cl2' C1' 1.78(3) . . yes Cl2A C1A 1.772(4) . . yes S1 C6 1.802(3) . . yes S1 C7 1.818(3) . . yes S2 C3 1.811(3) . . yes S2 C2 1.813(3) . . yes O1 C4 1.417(5) . . yes O1 C5 1.422(4) . . yes O2 C12 1.221(3) . . yes O3 C13 1.237(3) . . yes O4 C19 1.225(3) . . yes O5 C20 1.225(3) . . yes N1 C10 1.468(3) . . yes N1 C11 1.457(3) . . yes N1 C1 1.466(3) . . yes N2 C8 1.465(3) . . yes N2 C9 1.476(3) . . yes N2 C18 1.454(4) . . yes N3 C13 1.406(3) . . yes N3 C12 1.363(3) . . yes N4 C13 1.322(3) . . yes N4 C14 1.483(3) . . yes N5 C20 1.422(3) . . yes N5 C19 1.359(3) . . yes N6 C20 1.336(3) . . yes N6 C21 1.478(4) . . yes N3 H3N 0.88 . . no N4 H4N 0.88 . . no N5 H5N 0.88 . . no N6 H6N 0.88 . . no C1 C2 1.519(4) . . no C3 C4 1.509(6) . . no C5 C6 1.503(5) . . no C7 C8 1.517(4) . . no C9 C10 1.520(4) . . no C11 C12 1.533(4) . . no C14 C16 1.523(4) . . no C14 C15 1.529(4) . . no C14 C17 1.523(4) . . no C18 C19 1.522(4) . . no C21 C23 1.524(5) . . no C21 C24 1.525(4) . . no C21 C22 1.527(5) . . no C1 H1B 0.99 . . no C1 H1A 0.99 . . no C2 H2A 0.99 . . no C2 H2B 0.99 . . no C3 H3A 0.99 . . no C3 H3B 0.99 . . no C4 H4A 0.99 . . no C4 H4B 0.99 . . no C5 H5B 0.99 . . no C5 H5A 0.99 . . no C6 H6A 0.99 . . no C6 H6B 0.99 . . no C7 H7B 0.99 . . no C7 H7A 0.99 . . no C8 H8A 0.99 . . no C8 H8B 0.99 . . no C9 H9B 0.99 . . no C9 H9A 0.99 . . no C10 H10A 0.99 . . no C10 H10B 0.99 . . no C11 H11A 0.99 . . no C11 H11B 0.99 . . no C15 H15A 0.98 . . no C15 H15C 0.98 . . no C15 H15B 0.98 . . no C16 H16A 0.98 . . no C16 H16B 0.98 . . no C16 H16C 0.98 . . no C17 H17C 0.98 . . no C17 H17A 0.98 . . no C17 H17B 0.98 . . no C18 H18B 0.99 . . no C18 H18A 0.99 . . no C22 H22A 0.98 . . no C22 H22B 0.98 . . no C22 H22C 0.98 . . no C23 H23A 0.98 . . no C23 H23B 0.98 . . no C23 H23C 0.98 . . no C24 H24B 0.98 . . no C24 H24C 0.98 . . no C24 H24A 0.98 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C7 102.73(14) . . . yes C2 S2 C3 100.98(15) . . . yes C4 O1 C5 111.1(2) . . . yes C1 N1 C10 114.78(19) . . . yes C1 N1 C11 114.01(18) . . . yes C10 N1 C11 112.9(2) . . . yes C8 N2 C9 111.6(2) . . . yes C8 N2 C18 112.1(2) . . . yes C9 N2 C18 112.3(2) . . . yes C12 N3 C13 128.62(19) . . . yes C13 N4 C14 124.11(19) . . . yes C19 N5 C20 128.9(2) . . . yes C20 N6 C21 125.0(2) . . . yes C13 N3 H3N 116. . . . no C12 N3 H3N 116. . . . no C14 N4 H4N 118. . . . no C13 N4 H4N 118. . . . no C19 N5 H5N 116. . . . no C20 N5 H5N 116. . . . no C20 N6 H6N 118. . . . no C21 N6 H6N 117. . . . no N1 C1 C2 110.29(19) . . . yes S2 C2 C1 108.03(18) . . . yes S2 C3 C4 116.0(3) . . . yes O1 C4 C3 109.4(3) . . . yes O1 C5 C6 108.7(3) . . . yes S1 C6 C5 115.7(3) . . . yes S1 C7 C8 112.6(2) . . . yes N2 C8 C7 112.3(2) . . . yes N2 C9 C10 111.1(2) . . . yes N1 C10 C9 110.82(19) . . . yes N1 C11 C12 115.3(2) . . . yes N3 C12 C11 113.59(18) . . . yes O2 C12 N3 123.6(2) . . . yes O2 C12 C11 122.8(2) . . . yes O3 C13 N4 124.8(2) . . . yes N3 C13 N4 117.32(19) . . . yes O3 C13 N3 117.92(19) . . . yes N4 C14 C15 110.08(19) . . . yes N4 C14 C17 109.6(2) . . . yes C15 C14 C16 109.9(2) . . . no N4 C14 C16 105.30(19) . . . yes C15 C14 C17 111.1(2) . . . no C16 C14 C17 110.7(2) . . . no N2 C18 C19 115.1(2) . . . yes O4 C19 N5 125.1(3) . . . yes O4 C19 C18 119.6(2) . . . yes N5 C19 C18 115.3(2) . . . yes O5 C20 N5 118.1(2) . . . yes N5 C20 N6 115.1(2) . . . yes O5 C20 N6 126.8(2) . . . yes N6 C21 C23 110.5(2) . . . yes N6 C21 C24 109.5(2) . . . yes N6 C21 C22 105.3(2) . . . yes C22 C21 C24 109.9(3) . . . no C23 C21 C24 110.8(3) . . . no C22 C21 C23 110.8(3) . . . no N1 C1 H1A 110. . . . no N1 C1 H1B 110. . . . no C2 C1 H1A 110. . . . no C2 C1 H1B 110. . . . no H1A C1 H1B 108. . . . no S2 C2 H2A 110. . . . no S2 C2 H2B 110. . . . no C1 C2 H2A 110. . . . no C1 C2 H2B 110. . . . no H2A C2 H2B 108. . . . no S2 C3 H3A 108. . . . no S2 C3 H3B 108. . . . no C4 C3 H3A 108. . . . no C4 C3 H3B 108. . . . no H3A C3 H3B 107. . . . no O1 C4 H4A 110. . . . no O1 C4 H4B 110. . . . no C3 C4 H4A 110. . . . no C3 C4 H4B 110. . . . no H4A C4 H4B 108. . . . no O1 C5 H5A 110. . . . no O1 C5 H5B 110. . . . no C6 C5 H5A 110. . . . no C6 C5 H5B 110. . . . no H5A C5 H5B 108. . . . no S1 C6 H6A 108. . . . no S1 C6 H6B 108. . . . no C5 C6 H6A 108. . . . no C5 C6 H6B 108. . . . no H6A C6 H6B 107. . . . no S1 C7 H7A 109. . . . no S1 C7 H7B 109. . . . no C8 C7 H7A 109. . . . no C8 C7 H7B 109. . . . no H7A C7 H7B 108. . . . no N2 C8 H8A 109. . . . no N2 C8 H8B 109. . . . no C7 C8 H8A 109. . . . no C7 C8 H8B 109. . . . no H8A C8 H8B 108. . . . no N2 C9 H9A 109. . . . no N2 C9 H9B 109. . . . no C10 C9 H9A 109. . . . no C10 C9 H9B 109. . . . no H9A C9 H9B 108. . . . no N1 C10 H10A 109. . . . no N1 C10 H10B 109. . . . no C9 C10 H10A 110. . . . no C9 C10 H10B 110. . . . no H10A C10 H10B 108. . . . no N1 C11 H11A 108. . . . no N1 C11 H11B 108. . . . no C12 C11 H11A 108. . . . no C12 C11 H11B 108. . . . no H11A C11 H11B 107. . . . no C14 C15 H15A 109. . . . no C14 C15 H15B 110. . . . no C14 C15 H15C 109. . . . no H15A C15 H15B 109. . . . no H15A C15 H15C 109. . . . no H15B C15 H15C 109. . . . no C14 C16 H16A 109. . . . no C14 C16 H16B 109. . . . no C14 C16 H16C 109. . . . no H16A C16 H16B 109. . . . no H16A C16 H16C 109. . . . no H16B C16 H16C 109. . . . no C14 C17 H17A 109. . . . no C14 C17 H17B 109. . . . no C14 C17 H17C 109. . . . no H17A C17 H17B 110. . . . no H17A C17 H17C 110. . . . no H17B C17 H17C 109. . . . no N2 C18 H18A 108. . . . no N2 C18 H18B 108. . . . no C19 C18 H18A 108. . . . no C19 C18 H18B 109. . . . no H18A C18 H18B 108. . . . no C21 C22 H22A 109. . . . no C21 C22 H22B 109. . . . no C21 C22 H22C 109. . . . no H22A C22 H22B 109. . . . no H22A C22 H22C 110. . . . no H22B C22 H22C 109. . . . no C21 C23 H23A 109. . . . no C21 C23 H23B 109. . . . no C21 C23 H23C 109. . . . no H23A C23 H23B 109. . . . no H23A C23 H23C 110. . . . no H23B C23 H23C 109. . . . no C21 C24 H24A 109. . . . no C21 C24 H24B 109. . . . no C21 C24 H24C 109. . . . no H24A C24 H24B 109. . . . no H24A C24 H24C 109. . . . no H24B C24 H24C 109. . . . no Cl1' C1' Cl2' 89.6(10) . . . yes Cl1A C1A Cl2A 114.5(2) . . . yes 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 C7 S1 C6 C5 82.8(3) . . . . no C6 S1 C7 C8 74.5(2) . . . . no C3 S2 C2 C1 177.4(2) . . . . no C2 S2 C3 C4 82.4(3) . . . . no C5 O1 C4 C3 -176.2(3) . . . . no C4 O1 C5 C6 178.0(3) . . . . no C10 N1 C1 C2 -75.9(3) . . . . no C11 N1 C1 C2 151.6(2) . . . . no C1 N1 C10 C9 140.6(2) . . . . no C11 N1 C10 C9 -86.5(2) . . . . no C1 N1 C11 C12 65.7(3) . . . . no C10 N1 C11 C12 -67.7(2) . . . . no C9 N2 C8 C7 153.8(2) . . . . no C18 N2 C8 C7 -79.1(3) . . . . no C8 N2 C9 C10 -85.4(3) . . . . no C18 N2 C9 C10 147.6(2) . . . . no C8 N2 C18 C19 153.0(2) . . . . no C9 N2 C18 C19 -80.3(3) . . . . no C13 N3 C12 O2 -3.6(4) . . . . no C13 N3 C12 C11 173.9(2) . . . . no C12 N3 C13 O3 -179.1(2) . . . . no C12 N3 C13 N4 0.3(4) . . . . no C14 N4 C13 O3 -1.0(4) . . . . no C14 N4 C13 N3 179.7(2) . . . . no C13 N4 C14 C15 62.7(3) . . . . no C13 N4 C14 C16 -178.9(2) . . . . no C13 N4 C14 C17 -59.7(3) . . . . no C20 N5 C19 O4 1.4(4) . . . . no C20 N5 C19 C18 -177.5(2) . . . . no C19 N5 C20 O5 179.0(2) . . . . no C19 N5 C20 N6 -1.6(4) . . . . no C21 N6 C20 O5 -0.3(4) . . . . no C21 N6 C20 N5 -179.6(2) . . . . no C20 N6 C21 C22 -178.9(2) . . . . no C20 N6 C21 C23 -59.2(3) . . . . no C20 N6 C21 C24 63.0(3) . . . . no N1 C1 C2 S2 -176.89(19) . . . . no S2 C3 C4 O1 -66.0(4) . . . . no O1 C5 C6 S1 -69.9(3) . . . . no S1 C7 C8 N2 -179.16(18) . . . . no N2 C9 C10 N1 -66.2(3) . . . . no N1 C11 C12 O2 -48.4(4) . . . . no N1 C11 C12 N3 134.0(2) . . . . no N2 C18 C19 O4 171.7(2) . . . . no N2 C18 C19 N5 -9.3(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N3 H3N O3 0.88 1.88 2.758(3) 179 2_667 yes N4 H4N O2 0.88 2.02 2.705(3) 134 . yes N5 H5N N1 0.88 2.31 3.068(3) 144 . yes N5 H5N N2 0.88 2.25 2.728(3) 114 . yes N6 H6N O4 0.88 2.00 2.706(3) 137 . yes _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.46 _refine_diff_density_min -0.55 _refine_diff_density_rms 0.07 #===END of CIF data_(23) #S3N2PH _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H36 N4 O2 S3' _chemical_formula_sum 'C26 H36 N4 O2 S3' _chemical_formula_weight 532.77 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 'P 21/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 17.049(3) _cell_length_b 10.189(2) _cell_length_c 17.316(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.526(3) _cell_angle_gamma 90.00 _cell_volume 2714(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1019 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 28.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 24574 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.029 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 28.93 _reflns_number_total 6866 _reflns_number_gt 5027 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2000)' _refine_special_details ; ? ; _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^)+(0.060P)^2^] 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 ? _refine_ls_extinction_coef ? _refine_ls_number_reflns 6494 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.101 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.06765(8) 0.03673(11) 0.33609(8) 0.0254(3) Uani 1 1 d . . . O1 O 1.01000(8) -0.19507(12) 0.46185(7) 0.0448(3) Uani 1 1 d . . . C1 C 1.09734(9) 0.17391(13) 0.35081(10) 0.0277(3) Uani 1 1 d . . . H1A H 1.1088 0.2048 0.3024 0.033 Uiso 1 1 calc R . . H1B H 1.1523 0.1797 0.4037 0.033 Uiso 1 1 calc R . . S1 S 0.97826(2) 0.52093(4) 0.19415(2) 0.03391(11) Uani 1 1 d . . . S2 S 0.88519(3) 0.33776(4) 0.00167(3) 0.03966(12) Uani 1 1 d . . . N2 N 1.05347(7) 0.40040(11) 0.36791(7) 0.0247(3) Uani 1 1 d . . . O2 O 1.24732(8) 0.56693(14) 0.51924(7) 0.0480(3) Uani 1 1 d . . . C2 C 1.02938(9) 0.26055(13) 0.35926(9) 0.0249(3) Uani 1 1 d . . . H2A H 0.9734 0.2488 0.3082 0.030 Uiso 1 1 calc R . . H2B H 1.0211 0.2327 0.4100 0.030 Uiso 1 1 calc R . . S3 S 0.96710(3) -0.04348(4) 0.13261(2) 0.03321(11) Uani 1 1 d . . . N3 N 0.93554(8) -0.11638(11) 0.32523(7) 0.0260(3) Uani 1 1 d . . . H3A H 0.9404 -0.0592 0.2895 0.031 Uiso 1 1 calc R . . C3 C 0.97669(10) 0.48408(15) 0.34809(9) 0.0304(3) Uani 1 1 d . . . H3B H 0.9961 0.5750 0.3667 0.036 Uiso 1 1 calc R . . H3C H 0.9449 0.4524 0.3807 0.036 Uiso 1 1 calc R . . N4 N 1.18107(8) 0.56447(12) 0.37313(7) 0.0270(3) Uani 1 1 d . . . H4A H 1.1375 0.5276 0.3299 0.032 Uiso 1 1 calc R . . C4 C 0.91552(9) 0.48439(15) 0.25329(10) 0.0301(3) Uani 1 1 d . . . H4B H 0.8697 0.5514 0.2411 0.036 Uiso 1 1 calc R . . H4C H 0.8872 0.3976 0.2360 0.036 Uiso 1 1 calc R . . C5 C 0.89456(11) 0.57271(16) 0.09246(10) 0.0376(4) Uani 1 1 d . . . H5A H 0.8589 0.6408 0.1030 0.045 Uiso 1 1 calc R . . H5B H 0.9227 0.6140 0.0591 0.045 Uiso 1 1 calc R . . C6 C 0.83435(10) 0.46429(16) 0.03834(11) 0.0384(4) Uani 1 1 d . . . H6A H 0.7873 0.5051 -0.0124 0.046 Uiso 1 1 calc R . . H6B H 0.8071 0.4220 0.0722 0.046 Uiso 1 1 calc R . . C7 C 0.91424(11) 0.21373(15) 0.08557(10) 0.0346(3) Uani 1 1 d . . . H7A H 0.9650 0.2437 0.1375 0.041 Uiso 1 1 calc R . . H7B H 0.8651 0.1996 0.1007 0.041 Uiso 1 1 calc R . . C8 C 0.93583(10) 0.08697(15) 0.05345(9) 0.0323(3) Uani 1 1 d . . . H8A H 0.9840 0.1031 0.0372 0.039 Uiso 1 1 calc R . . H8B H 0.8846 0.0583 0.0015 0.039 Uiso 1 1 calc R . . C9 C 1.07992(10) -0.00105(16) 0.19833(10) 0.0307(3) Uani 1 1 d . . . H9A H 1.1172 -0.0460 0.1757 0.037 Uiso 1 1 calc R . . H9B H 1.0876 0.0947 0.1948 0.037 Uiso 1 1 calc R . . C10 C 1.10902(10) -0.03976(15) 0.29175(10) 0.0304(3) Uani 1 1 d . . . H10A H 1.0959 -0.1339 0.2943 0.036 Uiso 1 1 calc R . . H10B H 1.1728 -0.0287 0.3225 0.036 Uiso 1 1 calc R . . C11 C 1.07738(10) -0.02889(14) 0.41479(9) 0.0301(3) Uani 1 1 d . . . H11A H 1.0808 0.0386 0.4573 0.036 Uiso 1 1 calc R . . H11B H 1.1329 -0.0779 0.4385 0.036 Uiso 1 1 calc R . . C12 C 1.00413(10) -0.12307(14) 0.40296(9) 0.0290(3) Uani 1 1 d . . . C13 C 0.85697(9) -0.18867(13) 0.29344(10) 0.0264(3) Uani 1 1 d . . . C14 C 0.83317(10) -0.26628(15) 0.34680(11) 0.0331(3) Uani 1 1 d . . . H14A H 0.8689 -0.2698 0.4067 0.040 Uiso 1 1 calc R . . C15 C 0.75647(11) -0.33793(15) 0.31065(12) 0.0388(4) Uani 1 1 d . . . H15A H 0.7404 -0.3923 0.3461 0.047 Uiso 1 1 calc R . . C16 C 0.70351(10) -0.33138(16) 0.22446(13) 0.0417(4) Uani 1 1 d . . . H16A H 0.6515 -0.3815 0.2007 0.050 Uiso 1 1 calc R . . C17 C 0.72590(10) -0.25156(15) 0.17192(11) 0.0362(4) Uani 1 1 d . . . H17A H 0.6886 -0.2456 0.1125 0.043 Uiso 1 1 calc R . . C18 C 0.80291(9) -0.18057(14) 0.20653(10) 0.0297(3) Uani 1 1 d . . . H18A H 0.8186 -0.1265 0.1707 0.036 Uiso 1 1 calc R . . C19 C 1.12264(10) 0.43153(15) 0.45220(9) 0.0302(3) Uani 1 1 d . . . H19A H 1.1528 0.3491 0.4791 0.036 Uiso 1 1 calc R . . H19B H 1.0959 0.4673 0.4884 0.036 Uiso 1 1 calc R . . C20 C 1.18979(10) 0.52901(14) 0.45163(9) 0.0284(3) Uani 1 1 d . . . C21 C 1.23182(9) 0.65205(13) 0.35060(9) 0.0243(3) Uani 1 1 d . . . C22 C 1.30594(9) 0.71433(14) 0.41048(9) 0.0286(3) Uani 1 1 d . . . H22A H 1.3251 0.6982 0.4699 0.034 Uiso 1 1 calc R . . C23 C 1.35160(10) 0.80058(15) 0.38214(10) 0.0320(3) Uani 1 1 d . . . H23A H 1.4023 0.8427 0.4227 0.038 Uiso 1 1 calc R . . C24 C 1.32433(10) 0.82549(14) 0.29639(10) 0.0308(3) Uani 1 1 d . . . H24A H 1.3555 0.8854 0.2780 0.037 Uiso 1 1 calc R . . C25 C 1.25092(9) 0.76263(14) 0.23668(10) 0.0289(3) Uani 1 1 d . . . H25A H 1.2322 0.7789 0.1773 0.035 Uiso 1 1 calc R . . C26 C 1.20521(9) 0.67681(14) 0.26335(9) 0.0263(3) Uani 1 1 d . . . H26A H 1.1551 0.6340 0.2222 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0266(6) 0.0227(6) 0.0264(6) 0.0032(5) 0.0110(5) -0.0005(5) O1 0.0523(7) 0.0478(7) 0.0308(6) 0.0137(5) 0.0147(5) -0.0083(6) C1 0.0260(7) 0.0242(7) 0.0341(8) 0.0013(6) 0.0140(6) -0.0035(6) S1 0.0267(2) 0.0468(2) 0.0250(2) 0.00308(16) 0.00809(15) 0.00074(16) S2 0.0467(2) 0.0400(2) 0.0269(2) 0.00380(17) 0.01072(18) 0.00742(18) N2 0.0276(6) 0.0241(6) 0.0217(6) -0.0012(5) 0.0101(5) -0.0021(5) O2 0.0431(7) 0.0719(9) 0.0214(6) -0.0031(5) 0.0067(5) -0.0225(6) C2 0.0251(7) 0.0240(7) 0.0269(7) 0.0022(6) 0.0125(6) -0.0027(5) S3 0.0386(2) 0.0290(2) 0.0302(2) -0.00009(15) 0.01324(17) -0.00749(16) N3 0.0291(6) 0.0230(6) 0.0281(6) 0.0055(5) 0.0145(5) -0.0009(5) C3 0.0391(8) 0.0265(7) 0.0295(8) -0.0019(6) 0.0184(7) 0.0022(6) N4 0.0286(6) 0.0295(6) 0.0196(6) -0.0032(5) 0.0072(5) -0.0074(5) C4 0.0290(7) 0.0288(8) 0.0338(8) 0.0015(6) 0.0146(6) 0.0046(6) C5 0.0400(9) 0.0358(9) 0.0295(8) 0.0061(7) 0.0078(7) 0.0062(7) C6 0.0303(8) 0.0415(9) 0.0321(9) 0.0041(7) 0.0028(7) 0.0075(7) C7 0.0386(9) 0.0363(9) 0.0297(8) 0.0054(7) 0.0156(7) 0.0068(7) C8 0.0366(8) 0.0320(8) 0.0260(8) 0.0000(6) 0.0113(7) -0.0028(6) C9 0.0294(8) 0.0320(8) 0.0339(8) 0.0020(6) 0.0165(7) 0.0029(6) C10 0.0288(8) 0.0286(8) 0.0339(8) 0.0036(6) 0.0136(6) 0.0060(6) C11 0.0334(8) 0.0284(8) 0.0251(7) 0.0044(6) 0.0095(6) -0.0009(6) C12 0.0368(8) 0.0255(7) 0.0274(7) 0.0025(6) 0.0163(6) 0.0020(6) C13 0.0277(7) 0.0203(7) 0.0360(8) 0.0024(6) 0.0182(6) 0.0032(5) C14 0.0390(9) 0.0266(8) 0.0426(9) 0.0046(7) 0.0261(7) 0.0021(6) C15 0.0406(9) 0.0285(8) 0.0614(11) 0.0061(7) 0.0353(9) 0.0017(7) C16 0.0268(8) 0.0276(8) 0.0743(13) -0.0001(8) 0.0251(9) -0.0011(6) C17 0.0275(8) 0.0289(8) 0.0469(10) 0.0000(7) 0.0109(7) 0.0025(6) C18 0.0276(7) 0.0242(7) 0.0385(8) 0.0033(6) 0.0151(7) 0.0024(6) C19 0.0388(8) 0.0312(8) 0.0200(7) -0.0017(6) 0.0121(6) -0.0065(6) C20 0.0302(7) 0.0307(8) 0.0227(7) -0.0008(6) 0.0098(6) -0.0006(6) C21 0.0256(7) 0.0213(7) 0.0270(7) -0.0013(5) 0.0123(6) 0.0007(5) C22 0.0294(7) 0.0294(8) 0.0259(7) -0.0034(6) 0.0108(6) -0.0010(6) C23 0.0279(7) 0.0293(8) 0.0393(9) -0.0082(6) 0.0151(7) -0.0043(6) C24 0.0331(8) 0.0248(7) 0.0415(9) -0.0010(6) 0.0228(7) 0.0000(6) C25 0.0324(8) 0.0276(7) 0.0313(8) 0.0020(6) 0.0181(6) 0.0047(6) C26 0.0257(7) 0.0271(7) 0.0248(7) -0.0026(6) 0.0096(6) 0.0009(6) 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 C1 1.4709(18) . y N1 C10 1.4702(19) . y N1 C11 1.4619(18) . y O1 C12 1.2247(18) . y S1 C4 1.8098(16) . y S1 C5 1.8028(16) . y S2 C6 1.8141(18) . y S2 C7 1.8256(15) . y N2 C2 1.4726(18) . y N2 C3 1.4735(18) . y N2 C19 1.4623(18) . y O2 C20 1.2216(17) . y S3 C9 1.8153(16) . y S3 C8 1.8166(15) . y N3 C12 1.3518(18) . y N3 C13 1.4158(18) . y N4 C20 1.3514(18) . y N4 C21 1.4099(18) . y C1 C2 1.5130(19) . ? C3 C4 1.519(2) . ? C5 C6 1.524(2) . ? C7 C8 1.513(2) . ? C9 C10 1.525(2) . ? C11 C12 1.517(2) . ? C13 C18 1.388(2) . ? C13 C14 1.402(2) . ? C14 C15 1.389(2) . ? C15 C16 1.373(3) . ? C16 C17 1.391(2) . ? C17 C18 1.389(2) . ? C19 C20 1.519(2) . ? C21 C22 1.3948(19) . ? C21 C26 1.400(2) . ? C22 C23 1.396(2) . ? C23 C24 1.375(2) . ? C24 C25 1.389(2) . ? C25 C26 1.377(2) . ? 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 N1 C1 C2 110.51(11) . . ? N1 C10 C9 114.00(12) . . ? N1 C11 C12 114.03(12) . . ? N2 C2 C1 112.51(11) . . ? N2 C3 C4 112.35(12) . . ? N2 C19 C20 114.91(12) . . ? N3 C12 C11 114.28(12) . . ? N4 C20 C19 115.14(12) . . ? O1 C12 N3 125.76(14) . . ? O1 C12 C11 119.95(14) . . ? O2 C20 N4 125.05(14) . . ? O2 C20 C19 119.78(13) . . ? C2 N2 C3 110.81(11) . . y C3 C4 S1 108.30(10) . . ? C5 S1 C4 101.59(8) . . y C5 C6 S2 115.69(12) . . ? C6 C5 S1 115.36(11) . . ? C6 S2 C7 102.71(8) . . y C7 C8 S3 112.70(10) . . ? C8 C7 S2 108.89(10) . . ? C9 S3 C8 100.72(7) . . y C10 N1 C1 112.80(12) . . y C10 C9 S3 112.08(11) . . ? C11 N1 C1 112.38(12) . . y C11 N1 C10 110.92(11) . . y C12 N3 C13 128.95(12) . . ? C13 C18 C17 119.99(14) . . ? C14 C13 N3 122.07(14) . . ? C15 C14 C13 118.87(15) . . ? C15 C16 C17 120.14(15) . . ? C16 C15 C14 120.98(15) . . ? C18 C13 C14 120.17(14) . . ? C18 C13 N3 117.76(13) . . ? C18 C17 C16 119.82(16) . . ? C19 N2 C2 112.40(11) . . y C19 N2 C3 111.13(11) . . y C20 N4 C21 129.26(12) . . y C21 C22 C23 119.28(13) . . ? C22 C21 C26 119.24(13) . . ? C22 C21 N4 123.36(13) . . ? C23 C24 C25 119.71(14) . . ? C24 C23 C22 121.03(14) . . ? C25 C26 C21 120.62(14) . . ? C26 C21 N4 117.41(12) . . ? C26 C25 C24 120.11(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A N1 0.88 2.19 2.6791(17) 115 . N3 H3A S3 0.88 2.95 3.6762(13) 142 . N4 H4A N2 0.88 2.23 2.7140(17) 114 . N4 H4A S1 0.88 2.72 3.5386(13) 155 . _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.33 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.05 #===END of CIF data_[18.Ag][NO3] #S3NTAG _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H28 Ag N2 O S3 +, N O3 -' _chemical_formula_sum 'C14 H28 Ag N3 O4 S3' _chemical_formula_weight 506.44 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' 'Ag' 'Ag' -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.967(2) _cell_length_b 20.985(4) _cell_length_c 7.750(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.036(3) _cell_angle_gamma 90.00 _cell_volume 1943.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3889 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.95 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.384 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.825 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15778 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.065 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.71 _reflns_number_total 4691 _reflns_number_gt 3130 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2000)' _refine_special_details ; ? ; _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^)+(0.0139P)^2^] 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 ? _refine_ls_extinction_coef ? _refine_ls_number_reflns 4558 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0442 _refine_ls_wR_factor_gt 0.0404 _refine_ls_goodness_of_fit_ref 0.833 _refine_ls_restrained_S_all 0.833 _refine_ls_shift/su_max 0.002 _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 Ag Ag 0.865339(16) 0.818511(9) 0.81726(3) 0.01963(5) Uani 1 1 d . . . S1 S 0.84022(6) 0.92792(3) 0.97014(9) 0.02035(15) Uani 1 1 d . . . O1A O 0.63326(16) 1.06898(10) 0.3182(3) 0.0421(6) Uani 1 1 d . . . N1A N 0.66345(19) 1.01320(11) 0.3573(3) 0.0246(5) Uani 1 1 d . . . N1 N 1.01191(16) 0.88282(9) 0.6814(2) 0.0148(4) Uani 1 1 d . . . C1 C 1.0209(2) 0.94439(11) 0.7722(3) 0.0180(6) Uani 1 1 d . . . H1A H 1.0632 0.9745 0.7020 0.022 Uiso 1 1 calc R . . H1B H 1.0640 0.9382 0.8835 0.022 Uiso 1 1 calc R . . O1 O 1.09213(14) 0.80357(8) 0.9764(2) 0.0253(4) Uani 1 1 d . . . S2 S 0.64148(5) 0.83429(3) 0.74332(8) 0.02067(15) Uani 1 1 d . . . O2A O 0.60080(18) 0.96777(10) 0.3223(3) 0.0413(5) Uani 1 1 d . . . N2 N 1.25765(16) 0.85329(9) 0.9329(3) 0.0160(5) Uani 1 1 d . . . H2A H 1.2914 0.8773 0.8585 0.019 Uiso 1 1 calc R . . C2 C 0.9083(2) 0.97376(11) 0.8071(3) 0.0176(6) Uani 1 1 d . . . H2B H 0.8603 0.9745 0.6990 0.021 Uiso 1 1 calc R . . H2C H 0.9191 1.0182 0.8473 0.021 Uiso 1 1 calc R . . S3 S 0.84807(5) 0.78598(3) 0.47778(8) 0.01618(14) Uani 1 1 d . . . O3A O 0.75669(15) 1.00449(9) 0.4345(3) 0.0331(5) Uani 1 1 d . . . C3 C 0.6936(2) 0.94483(12) 0.9214(3) 0.0237(6) Uani 1 1 d . . . H3A H 0.6504 0.9264 1.0149 0.028 Uiso 1 1 calc R . . H3B H 0.6833 0.9916 0.9249 0.028 Uiso 1 1 calc R . . C4 C 0.6427(2) 0.92088(11) 0.7507(3) 0.0231(6) Uani 1 1 d . . . H4A H 0.6862 0.9375 0.6554 0.028 Uiso 1 1 calc R . . H4B H 0.5651 0.9370 0.7340 0.028 Uiso 1 1 calc R . . C5 C 0.62468(19) 0.81838(13) 0.5142(3) 0.0229(6) Uani 1 1 d . . . H5A H 0.6043 0.7729 0.4985 0.027 Uiso 1 1 calc R . . H5B H 0.5609 0.8440 0.4662 0.027 Uiso 1 1 calc R . . C6 C 0.7255(2) 0.83203(12) 0.4083(3) 0.0206(6) Uani 1 1 d . . . H6A H 0.7439 0.8780 0.4171 0.025 Uiso 1 1 calc R . . H6B H 0.7058 0.8224 0.2853 0.025 Uiso 1 1 calc R . . C7 C 0.9577(2) 0.83378(11) 0.3938(3) 0.0174(6) Uani 1 1 d . . . H7A H 1.0268 0.8079 0.3923 0.021 Uiso 1 1 calc R . . H7B H 0.9360 0.8457 0.2730 0.021 Uiso 1 1 calc R . . C8 C 0.9824(2) 0.89392(11) 0.4971(3) 0.0164(5) Uani 1 1 d . . . H8A H 1.0449 0.9167 0.4456 0.020 Uiso 1 1 calc R . . H8B H 0.9159 0.9220 0.4872 0.020 Uiso 1 1 calc R . . C9 C 1.1199(2) 0.84920(11) 0.6987(3) 0.0176(6) Uani 1 1 d . . . H9A H 1.1784 0.8761 0.6497 0.021 Uiso 1 1 calc R . . H9B H 1.1146 0.8092 0.6310 0.021 Uiso 1 1 calc R . . C10 C 1.1544(2) 0.83348(11) 0.8851(3) 0.0178(6) Uani 1 1 d . . . C11 C 1.3214(2) 0.83905(11) 1.0978(3) 0.0177(6) Uani 1 1 d . . . C12 C 1.2596(2) 0.86350(14) 1.2504(3) 0.0325(7) Uani 1 1 d . . . H12A H 1.2484 0.9096 1.2390 0.049 Uiso 1 1 calc R . . H12B H 1.3037 0.8544 1.3578 0.049 Uiso 1 1 calc R . . H12C H 1.1868 0.8423 1.2530 0.049 Uiso 1 1 calc R . . C13 C 1.3419(2) 0.76781(12) 1.1106(4) 0.0268(7) Uani 1 1 d . . . H13A H 1.3820 0.7536 1.0105 0.040 Uiso 1 1 calc R . . H13B H 1.2700 0.7455 1.1126 0.040 Uiso 1 1 calc R . . H13C H 1.3868 0.7584 1.2169 0.040 Uiso 1 1 calc R . . C14 C 1.4333(2) 0.87336(12) 1.0878(3) 0.0251(6) Uani 1 1 d . . . H14A H 1.4725 0.8571 0.9890 0.038 Uiso 1 1 calc R . . H14B H 1.4791 0.8658 1.1945 0.038 Uiso 1 1 calc R . . H14C H 1.4202 0.9192 1.0736 0.038 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 Ag 0.02277(11) 0.01497(9) 0.02110(10) 0.00321(10) 0.00072(7) 0.00022(10) S1 0.0236(4) 0.0200(3) 0.0175(4) -0.0004(3) 0.0013(3) -0.0008(3) O1A 0.0269(12) 0.0371(13) 0.0624(16) 0.0313(11) 0.0050(11) 0.0024(10) N1A 0.0212(14) 0.0341(15) 0.0187(13) 0.0057(11) 0.0033(10) -0.0015(11) N1 0.0152(11) 0.0116(10) 0.0172(11) -0.0018(9) -0.0023(9) 0.0019(8) C1 0.0155(14) 0.0175(14) 0.0207(15) -0.0035(11) -0.0014(11) -0.0016(10) O1 0.0160(10) 0.0294(11) 0.0305(11) 0.0083(8) 0.0007(8) -0.0057(8) S2 0.0198(4) 0.0201(4) 0.0224(4) 0.0015(3) 0.0032(3) 0.0005(3) O2A 0.0429(14) 0.0374(13) 0.0427(14) -0.0057(11) -0.0047(11) -0.0105(11) N2 0.0143(11) 0.0195(11) 0.0142(11) 0.0040(9) 0.0001(9) -0.0013(9) C2 0.0205(14) 0.0138(13) 0.0187(14) -0.0011(10) 0.0014(11) -0.0007(10) S3 0.0159(3) 0.0155(3) 0.0169(4) -0.0028(3) -0.0003(3) -0.0004(3) O3A 0.0197(11) 0.0397(12) 0.0393(13) 0.0154(10) -0.0025(9) 0.0013(9) C3 0.0242(16) 0.0178(14) 0.0298(17) -0.0017(12) 0.0087(13) 0.0039(12) C4 0.0204(15) 0.0178(14) 0.0312(16) 0.0041(12) 0.0021(12) 0.0050(11) C5 0.0180(13) 0.0274(14) 0.0231(14) -0.0022(13) -0.0016(11) 0.0023(13) C6 0.0194(14) 0.0241(15) 0.0179(14) -0.0020(11) -0.0024(11) 0.0047(11) C7 0.0170(13) 0.0200(14) 0.0152(13) -0.0019(10) 0.0019(11) -0.0016(10) C8 0.0163(14) 0.0162(13) 0.0166(14) 0.0022(10) 0.0000(11) -0.0014(10) C9 0.0148(14) 0.0185(12) 0.0191(14) -0.0019(11) -0.0019(11) 0.0017(11) C10 0.0175(14) 0.0139(13) 0.0220(14) -0.0006(10) -0.0002(11) 0.0023(10) C11 0.0151(14) 0.0217(14) 0.0160(14) 0.0002(10) -0.0009(11) 0.0011(10) C12 0.0331(18) 0.0450(19) 0.0196(17) -0.0016(13) 0.0038(13) 0.0084(14) C13 0.0293(17) 0.0239(15) 0.0263(16) 0.0075(12) -0.0055(13) 0.0011(12) C14 0.0186(15) 0.0295(16) 0.0263(16) 0.0005(12) -0.0063(12) -0.0041(12) 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 Ag N1 2.490(2) . y Ag S1 2.6082(8) . y Ag S2 2.7299(8) . y Ag S3 2.7153(9) . y Ag S3 2.5349(8) 4_576 y N1 C1 1.472(3) . ? N1 C8 1.471(3) . ? N1 C9 1.472(3) . ? N2 C10 1.337(3) . ? N2 C11 1.484(3) . ? O1 C10 1.227(3) . ? S1 C2 1.815(2) . ? S1 C3 1.811(3) . ? S2 C4 1.818(2) . ? S2 C5 1.808(2) . ? S3 C6 1.814(2) . ? S3 C7 1.800(2) . ? C1 C2 1.519(3) . ? C3 C4 1.513(4) . ? C5 C6 1.522(3) . ? C7 C8 1.515(3) . ? C9 C10 1.518(3) . ? C11 C12 1.517(3) . ? C11 C13 1.517(3) . ? C11 C14 1.526(3) . ? N1A O1A 1.257(3) . ? N1A O2A 1.234(3) . ? N1A O3A 1.251(3) . ? 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 N1 Ag S1 79.39(5) . . y N1 Ag S2 123.42(5) . . y N1 Ag S3 75.27(5) . . y N1 Ag S3 138.92(5) . 4_576 y S1 Ag S3 131.05(2) . . y S1 Ag S2 81.55(2) . . y S3 Ag S1 121.61(3) 4_576 . y S3 Ag S2 78.68(2) . . y S3 Ag S2 95.93(2) 4_576 . y S3 Ag S3 104.717(17) 4_576 . y Ag S3 Ag 133.55(3) 4_575 . y C2 S1 Ag 94.79(8) . . ? C3 S1 Ag 102.21(8) . . ? C4 S2 Ag 96.24(9) . . ? C5 S2 Ag 103.92(8) . . ? C6 S3 Ag 99.94(8) . . ? C7 S3 Ag 100.99(8) . . ? C6 S3 Ag 113.62(8) . 4_575 ? C7 S3 Ag 102.99(8) . 4_575 ? C1 N1 Ag 107.98(14) . . ? C8 N1 Ag 110.98(14) . . ? C9 N1 Ag 109.65(14) . . ? C7 S3 C6 100.89(12) . . ? C8 N1 C9 109.20(19) . . ? C8 N1 C1 109.42(18) . . ? C9 N1 C1 109.59(18) . . ? N1 C1 C2 113.45(19) . . ? N1 C8 C7 114.27(19) . . ? N1 C9 C10 112.6(2) . . ? N2 C10 C9 113.4(2) . . ? N2 C11 C12 110.7(2) . . ? N2 C11 C13 109.2(2) . . ? N2 C11 C14 105.9(2) . . ? O1 C10 N2 125.5(2) . . ? O1 C10 C9 121.1(2) . . ? C1 C2 S1 110.10(17) . . ? C3 S1 C2 102.50(12) . . ? C3 C4 S2 111.21(18) . . ? C4 C3 S1 117.27(18) . . ? C5 C6 S3 113.03(17) . . ? C5 S2 C4 102.47(13) . . ? C6 C5 S2 116.41(17) . . ? C8 C7 S3 113.50(17) . . ? C10 N2 C11 127.0(2) . . ? C12 C11 C13 111.5(2) . . ? C12 C11 C14 110.2(2) . . ? C13 C11 C14 109.2(2) . . ? O2A N1A O3A 120.5(2) . . ? O2A N1A O1A 120.2(2) . . ? O3A N1A O1A 119.3(2) . . ? 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 N2 H2A O1A 0.88 2.02 2.901(3) 178 3_776 _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.60 _refine_diff_density_min -0.38 _refine_diff_density_rms 0.08 #===END of CIF