# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Fedorov, Yuri V.' 'Fedorov, Olga A.' 'Andryukhina, Elena N.' 'Gromov, Sergey P.' 'Alfimov, Michael V.' 'Kuzmina, Lyudmila G.' 'Churakov, Andrei V.' 'Howard, Judith A. K.' 'Aaron, J.-J.' _publ_contact_author_name 'Prof Jean-Jacques Aaron' _publ_contact_author_address ; Institut de Topologie et de Dynamique des Systemes Universite Paris-7-Denis Did 1, rue Guy de la Brosse Paris 75005 FRANCE ; _publ_contact_author_email AARON@PARIS7.JUSSIEU.FR _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Ditopic complex formation of the crown-containing 2-styrylbenzothiazole. ; data_a _database_code_CSD 185189 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H25 N O5 S' _chemical_formula_weight 427.50 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0566(7) _cell_length_b 14.156(2) _cell_length_c 28.558(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.492(8) _cell_angle_gamma 90.00 _cell_volume 2040.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method ? _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type 'Empirical' _exptl_absorpt_correction_T_min 0.52652 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17287 _diffrn_reflns_av_R_equivalents 0.0921 _diffrn_reflns_av_sigmaI/netI 0.0928 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4934 _reflns_number_observed 2775 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 817 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0055(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4117 _refine_ls_number_parameters 410 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_obs 0.0522 _refine_ls_wR_factor_all 0.1372 _refine_ls_wR_factor_obs 0.1046 _refine_ls_goodness_of_fit_all 1.005 _refine_ls_goodness_of_fit_obs 1.116 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.116 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -1.6252(3) 0.46818(11) -0.22100(5) 0.0245(4) Uani 1 d . . O2 O -1.4569(3) 0.53920(11) -0.30775(6) 0.0272(4) Uani 1 d . . O3 O -1.9148(3) 0.67437(12) -0.33556(6) 0.0322(4) Uani 1 d . . O4 O -2.1164(3) 0.75635(11) -0.22251(6) 0.0279(4) Uani 1 d . . O5 O -1.9362(3) 0.57958(11) -0.17981(5) 0.0235(4) Uani 1 d . . C1 C -1.4209(5) 0.4244(2) -0.24666(9) 0.0244(6) Uani 1 d . . C2 C -1.4905(6) 0.4414(2) -0.29759(9) 0.0280(6) Uani 1 d . . C3 C -1.5544(6) 0.5663(2) -0.35384(9) 0.0339(6) Uani 1 d . . C4 C -1.8447(6) 0.5879(2) -0.35753(10) 0.0359(7) Uani 1 d . . C5 C -1.9222(5) 0.6695(2) -0.28585(9) 0.0246(6) Uani 1 d . . C6 C -2.1179(5) 0.7445(2) -0.27240(9) 0.0261(6) Uani 1 d . . C7 C -2.2748(5) 0.6893(2) -0.19904(9) 0.0257(6) Uani 1 d . . C8 C -2.1155(5) 0.6442(2) -0.15914(9) 0.0244(5) Uani 1 d . . C9 C -1.7642(4) 0.5296(2) -0.15049(8) 0.0210(5) Uani 1 d . . C10 C -1.5924(5) 0.4679(2) -0.17281(8) 0.0223(5) Uani 1 d . . C11 C -1.4114(5) 0.4138(2) -0.14650(9) 0.0276(6) Uani 1 d . . C12 C -1.3904(5) 0.4217(2) -0.09710(10) 0.0314(6) Uani 1 d . . C13 C -1.5575(5) 0.4833(2) -0.07550(10) 0.0314(6) Uani 1 d . . C14 C -1.7456(5) 0.5370(2) -0.10207(9) 0.0277(6) Uani 1 d . . S1 S -0.7316(10) 0.2067(3) -0.04739(11) 0.0241(7) Uani 0.511(5) d P 1 N1 N -0.7805(29) 0.2977(10) 0.0317(4) 0.030(3) Uani 0.511(5) d P 1 C15 C -1.1773(17) 0.3542(6) -0.0765(3) 0.021(2) Uani 0.511(5) d P 1 H15A H -1.1008(17) 0.3107(6) -0.0971(3) 0.025 Uiso 0.511(5) calc PR 1 C16 C -1.0933(9) 0.3529(3) -0.0316(2) 0.0229(12) Uani 0.511(5) d P 1 H16A H -1.1770(9) 0.3943(3) -0.0109(2) 0.027 Uiso 0.511(5) calc PR 1 C17 C -0.8821(10) 0.2928(4) -0.0119(2) 0.0199(11) Uani 0.511(5) d P 1 S1' S -0.8015(10) 0.3162(3) 0.01918(14) 0.0251(7) Uani 0.489(5) d P 2 N1' N -0.7030(34) 0.2001(13) -0.0461(5) 0.056(7) Uani 0.489(5) d P 2 C15' C -1.2102(20) 0.3787(6) -0.0621(3) 0.026(2) Uani 0.489(5) d P 2 H15B H -1.2159(20) 0.3987(6) -0.0304(3) 0.031 Uiso 0.489(5) calc PR 2 C16' C -1.0341(11) 0.3116(4) -0.0726(2) 0.0234(12) Uani 0.489(5) d P 2 H16B H -1.0311(11) 0.2909(4) -0.1042(2) 0.028 Uiso 0.489(5) calc PR 2 C17' C -0.8481(10) 0.2692(4) -0.0376(2) 0.0189(12) Uani 0.489(5) d P 2 C18 C -0.5305(5) 0.1747(2) -0.00329(9) 0.0273(6) Uani 1 d . . C19 C -0.5736(5) 0.2309(2) 0.03630(9) 0.0259(6) Uani 1 d . . C20 C -0.4244(5) 0.2159(2) 0.07858(10) 0.0307(6) Uani 1 d . . C21 C -0.2340(5) 0.1459(2) 0.08035(11) 0.0349(7) Uani 1 d . . C22 C -0.1905(6) 0.0907(2) 0.04169(11) 0.0424(8) Uani 1 d . . C23 C -0.3369(6) 0.1040(2) -0.00026(11) 0.0407(7) Uani 1 d . . H1A H -1.4231(44) 0.3556(17) -0.2403(8) 0.022(6) Uiso 1 d . . H1B H -1.2441(48) 0.4520(16) -0.2376(8) 0.020(6) Uiso 1 d . . H2A H -1.3718(49) 0.4029(17) -0.3173(9) 0.030(7) Uiso 1 d . . H2B H -1.6751(52) 0.4225(17) -0.3058(9) 0.029(7) Uiso 1 d . . H3A H -1.5287(48) 0.5116(17) -0.3787(9) 0.032(7) Uiso 1 d . . H3B H -1.4717(71) 0.6328(25) -0.3632(12) 0.081(12) Uiso 1 d . . H4A H -1.9113(60) 0.5983(20) -0.3940(12) 0.059(9) Uiso 1 d . . H4B H -1.9500(54) 0.5328(19) -0.3449(10) 0.043(8) Uiso 1 d . . H5A H -1.7418(47) 0.6835(15) -0.2690(8) 0.021(6) Uiso 1 d . . H5B H -1.9871(45) 0.6048(16) -0.2754(8) 0.024(6) Uiso 1 d . . H6A H -2.0611(45) 0.8045(17) -0.2850(8) 0.023(6) Uiso 1 d . . H6B H -2.3063(56) 0.7253(17) -0.2874(10) 0.037(7) Uiso 1 d . . H7A H -2.3545(43) 0.6426(16) -0.2206(8) 0.015(6) Uiso 1 d . . H7B H -2.4359(49) 0.7231(16) -0.1865(8) 0.027(7) Uiso 1 d . . H8A H -2.0106(48) 0.6917(17) -0.1399(9) 0.027(7) Uiso 1 d . . H8B H -2.2357(47) 0.6079(16) -0.1375(8) 0.023(6) Uiso 1 d . . H11A H -1.2943(50) 0.3707(17) -0.1609(9) 0.031(7) Uiso 1 d . . H13A H -1.5502(57) 0.4887(19) -0.0405(11) 0.051(9) Uiso 1 d . . H14A H -1.8592(50) 0.5808(17) -0.0859(9) 0.032(7) Uiso 1 d . . H20A H -0.4613(63) 0.2533(22) 0.1027(12) 0.058(10) Uiso 1 d . . H21A H -0.1264(54) 0.1383(19) 0.1097(10) 0.042(8) Uiso 1 d . . H22A H -0.0604(60) 0.0435(21) 0.0441(11) 0.054(9) Uiso 1 d . . H23A H -0.3108(54) 0.0621(19) -0.0269(10) 0.042(8) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0234(9) 0.0300(9) 0.0199(9) 0.0009(7) 0.0010(7) 0.0060(7) O2 0.0311(10) 0.0246(9) 0.0260(10) 0.0045(7) 0.0024(8) 0.0013(7) O3 0.0361(11) 0.0344(10) 0.0267(10) 0.0045(8) 0.0062(9) 0.0076(8) O4 0.0288(10) 0.0246(9) 0.0304(10) -0.0009(7) 0.0029(8) -0.0026(7) O5 0.0232(9) 0.0277(9) 0.0195(9) 0.0011(7) 0.0009(7) 0.0069(7) C1 0.0226(14) 0.0227(12) 0.0285(14) -0.0009(10) 0.0063(11) 0.0031(10) C2 0.032(2) 0.0253(12) 0.0278(14) -0.0045(10) 0.0078(13) -0.0013(11) C3 0.038(2) 0.042(2) 0.0219(14) 0.0028(12) 0.0057(13) 0.0067(13) C4 0.035(2) 0.045(2) 0.028(2) -0.0009(13) 0.0018(13) 0.0040(13) C5 0.0213(13) 0.0296(13) 0.0230(14) 0.0026(10) 0.0007(11) -0.0003(10) C6 0.0221(14) 0.0271(13) 0.0290(14) 0.0038(11) 0.0018(11) -0.0007(11) C7 0.0219(13) 0.0256(13) 0.0302(15) -0.0011(11) 0.0063(12) 0.0003(11) C8 0.0217(13) 0.0260(12) 0.0256(14) -0.0037(11) 0.0019(11) 0.0026(10) C9 0.0147(12) 0.0257(12) 0.0222(13) 0.0060(10) -0.0013(10) -0.0030(9) C10 0.0187(12) 0.0265(12) 0.0215(13) 0.0034(10) -0.0015(10) -0.0020(10) C11 0.0222(14) 0.0261(13) 0.034(2) 0.0056(11) -0.0008(12) -0.0009(11) C12 0.0191(13) 0.0379(15) 0.036(2) 0.0171(12) -0.0086(12) -0.0046(11) C13 0.0278(15) 0.046(2) 0.0192(14) 0.0077(11) -0.0067(12) -0.0115(12) C14 0.0262(14) 0.0345(14) 0.0219(14) 0.0007(11) -0.0013(11) -0.0057(11) S1 0.0241(11) 0.035(2) 0.0134(13) -0.0026(10) -0.0004(9) -0.0005(11) N1 0.027(4) 0.038(6) 0.024(6) -0.006(3) -0.002(4) 0.002(4) C15 0.019(4) 0.022(4) 0.022(4) 0.002(3) 0.000(3) 0.005(3) C16 0.020(3) 0.025(2) 0.024(3) 0.003(2) 0.001(2) 0.004(2) C17 0.023(3) 0.027(3) 0.010(3) -0.002(2) -0.002(3) -0.003(2) S1' 0.0242(10) 0.0292(13) 0.021(2) -0.0042(11) -0.0044(12) 0.0073(9) N1' 0.061(11) 0.050(9) 0.056(10) -0.009(6) 0.004(6) 0.005(6) C15' 0.025(4) 0.024(4) 0.028(5) -0.007(3) 0.003(4) 0.001(3) C16' 0.024(3) 0.026(3) 0.019(3) 0.001(2) -0.003(2) -0.003(2) C17' 0.017(3) 0.021(3) 0.018(3) -0.002(2) -0.001(2) -0.003(2) C18 0.0217(13) 0.0289(13) 0.0317(15) 0.0052(11) 0.0046(12) 0.0016(11) C19 0.0236(14) 0.0263(12) 0.0275(14) 0.0062(10) -0.0007(11) -0.0019(10) C20 0.0284(15) 0.0354(14) 0.0278(15) 0.0043(12) -0.0016(12) 0.0007(11) C21 0.0268(15) 0.041(2) 0.037(2) 0.0166(13) 0.0013(13) 0.0019(12) C22 0.035(2) 0.045(2) 0.048(2) 0.0172(14) 0.0118(15) 0.0197(14) C23 0.041(2) 0.042(2) 0.040(2) 0.0078(13) 0.0134(15) 0.0167(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.376(3) . ? O1 C1 1.442(3) . ? O2 C2 1.427(3) . ? O2 C3 1.430(3) . ? O3 C5 1.424(3) . ? O3 C4 1.430(3) . ? O4 C6 1.434(3) . ? O4 C7 1.434(3) . ? O5 C9 1.367(3) . ? O5 C8 1.440(3) . ? C1 C2 1.495(4) . ? C3 C4 1.497(4) . ? C5 C6 1.517(3) . ? C7 C8 1.497(3) . ? C9 C14 1.384(3) . ? C9 C10 1.411(3) . ? C10 C11 1.381(3) . ? C11 C12 1.413(4) . ? C12 C13 1.385(4) . ? C12 C15' 1.444(11) . ? C12 C15 1.530(9) . ? C13 C14 1.403(4) . ? S1 C18 1.634(5) . ? S1 C17 1.785(8) . ? N1 C17 1.320(11) . ? N1 C19 1.410(13) . ? C15 C16 1.327(10) . ? C16 C17 1.453(7) . ? S1' C19 1.719(4) . ? S1' C17' 1.757(8) . ? N1' C17' 1.26(2) . ? N1' C18 1.50(2) . ? C15' C16' 1.349(9) . ? C16' C17' 1.458(8) . ? C18 C23 1.399(4) . ? C18 C19 1.410(4) . ? C19 C20 1.400(4) . ? C20 C21 1.381(4) . ? C21 C22 1.381(4) . ? C22 C23 1.382(4) . ? 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 C10 O1 C1 117.4(2) . . ? C2 O2 C3 114.1(2) . . ? C5 O3 C4 114.7(2) . . ? C6 O4 C7 114.7(2) . . ? C9 O5 C8 118.1(2) . . ? O1 C1 C2 107.0(2) . . ? O2 C2 C1 109.2(2) . . ? O2 C3 C4 113.7(2) . . ? O3 C4 C3 114.3(2) . . ? O3 C5 C6 106.0(2) . . ? O4 C6 C5 111.7(2) . . ? O4 C7 C8 110.4(2) . . ? O5 C8 C7 106.4(2) . . ? O5 C9 C14 125.1(2) . . ? O5 C9 C10 115.4(2) . . ? C14 C9 C10 119.4(2) . . ? O1 C10 C11 125.5(2) . . ? O1 C10 C9 114.2(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 120.4(2) . . ? C13 C12 C11 118.9(2) . . ? C13 C12 C15' 109.5(4) . . ? C11 C12 C15' 131.5(4) . . ? C13 C12 C15 131.1(4) . . ? C11 C12 C15 110.0(4) . . ? C12 C13 C14 120.8(2) . . ? C9 C14 C13 120.1(2) . . ? C18 S1 C17 91.0(3) . . ? C17 N1 C19 107.2(10) . . ? C16 C15 C12 123.8(6) . . ? C15 C16 C17 124.6(5) . . ? N1 C17 C16 124.8(7) . . ? N1 C17 S1 114.7(7) . . ? C16 C17 S1 120.6(5) . . ? C19 S1' C17' 92.7(3) . . ? C17' N1' C18 110.2(11) . . ? C16' C15' C12 122.7(7) . . ? C15' C16' C17' 123.0(6) . . ? N1' C17' C16' 123.3(9) . . ? N1' C17' S1' 115.3(8) . . ? C16' C17' S1' 121.4(4) . . ? C23 C18 C19 119.7(3) . . ? C23 C18 N1' 126.2(7) . . ? C19 C18 N1' 114.1(7) . . ? C23 C18 S1 130.3(3) . . ? C19 C18 S1 110.0(2) . . ? C20 C19 N1 122.6(6) . . ? C20 C19 C18 120.3(2) . . ? N1 C19 C18 117.0(6) . . ? C20 C19 S1' 131.9(3) . . ? C18 C19 S1' 107.6(2) . . ? C21 C20 C19 118.6(3) . . ? C20 C21 C22 121.4(3) . . ? C23 C22 C21 120.8(3) . . ? C22 C23 C18 119.2(3) . . ? _refine_diff_density_max 0.489 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.056 data_abs _database_code_CSD 185190 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H28 Ag2 N4 O11 S' _chemical_formula_weight 808.31 _chemical_melting_point ? _chemical_compound_source ? 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 Triclinic _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4310(5) _cell_length_b 11.6540(6) _cell_length_c 13.4464(7) _cell_angle_alpha 88.270(3) _cell_angle_beta 81.119(3) _cell_angle_gamma 76.369(3) _cell_volume 1419.00(13) _cell_formula_units_Z 2 _cell_measurement_temperature 102(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.892 _exptl_crystal_density_method ? _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.521 _exptl_absorpt_correction_type 'Empirical' _exptl_absorpt_correction_T_min 0.74396 _exptl_absorpt_correction_T_max 0.84117 _exptl_special_details ; ? ; _diffrn_ambient_temperature 102.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16240 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_sigmaI/netI 0.1091 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.50 _reflns_number_total 7139 _reflns_number_observed 4419 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 880 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6259 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1080 _refine_ls_R_factor_obs 0.0550 _refine_ls_wR_factor_all 0.1278 _refine_ls_wR_factor_obs 0.1062 _refine_ls_goodness_of_fit_all 1.011 _refine_ls_goodness_of_fit_obs 1.116 _refine_ls_restrained_S_all 1.040 _refine_ls_restrained_S_obs 1.116 _refine_ls_shift/esd_max -2.141 _refine_ls_shift/esd_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ag1 Ag 0.00824(5) 0.86048(4) 0.41790(3) 0.02060(13) Uani 1 d . . Ag2 Ag -0.28880(6) 0.64503(4) -0.15041(4) 0.0310(2) Uani 1 d . . S1 S -0.3084(2) 0.28392(13) 0.02039(12) 0.0260(3) Uani 1 d . . O1 O 0.0575(4) 0.7632(3) 0.2332(3) 0.0180(8) Uani 1 d . . O2 O -0.0149(4) 1.0061(3) 0.2670(3) 0.0200(8) Uani 1 d . . O3 O 0.1851(4) 0.9827(3) 0.4106(3) 0.0237(9) Uani 1 d . . O4 O 0.2157(4) 0.7707(3) 0.5306(3) 0.0252(9) Uani 1 d . . O5 O 0.1770(4) 0.6396(3) 0.3717(3) 0.0170(8) Uani 1 d . . O6 O -0.1444(4) 0.7389(4) 0.4967(3) 0.0273(10) Uani 1 d . . O7 O -0.2605(5) 0.8482(4) 0.3887(3) 0.0318(10) Uani 1 d . . O8 O -0.3525(5) 0.7111(4) 0.4681(4) 0.0385(12) Uani 1 d . . O9 O -0.2571(5) 0.9415(4) 0.0054(3) 0.0324(10) Uani 1 d . . O10 O -0.1545(5) 0.7585(4) -0.0355(3) 0.0369(11) Uani 1 d . . O11 O -0.3424(5) 0.8502(4) -0.1038(3) 0.0394(12) Uani 1 d . . N1 N -0.3339(5) 0.4758(4) -0.0861(3) 0.0209(10) Uani 1 d . . N2 N -0.2540(5) 0.7653(4) 0.4506(4) 0.0215(11) Uani 1 d . . N3 N -0.2520(6) 0.8516(4) -0.0424(4) 0.0244(11) Uani 1 d . . N4 N -0.4516(7) 0.7255(5) -0.2750(4) 0.042(2) Uani 1 d . . C1 C -0.0222(6) 0.8429(4) 0.1661(4) 0.0175(12) Uani 1 d . . H1A H -0.1299(6) 0.8576(4) 0.1891(4) 0.021 Uiso 1 calc R . H1B H -0.0004(6) 0.8097(4) 0.0970(4) 0.021 Uiso 1 calc R . C2 C 0.0291(6) 0.9552(5) 0.1684(4) 0.0202(12) Uani 1 d . . H2A H 0.1379(6) 0.9384(5) 0.1508(4) 0.024 Uiso 1 calc R . H2B H -0.0146(6) 1.0113(5) 0.1185(4) 0.024 Uiso 1 calc R . C3 C 0.0583(7) 1.0952(5) 0.2864(5) 0.0236(13) Uani 1 d . . H3A H -0.0042(7) 1.1482(5) 0.3405(5) 0.028 Uiso 1 calc R . H3B H 0.0708(7) 1.1432(5) 0.2250(5) 0.028 Uiso 1 calc R . C4 C 0.2077(7) 1.0444(5) 0.3174(5) 0.0285(14) Uani 1 d . . H4B H 0.2706(7) 0.9894(5) 0.2649(5) 0.034 Uiso 1 calc R . H4C H 0.2575(7) 1.1085(5) 0.3263(5) 0.034 Uiso 1 calc R . C5 C 0.3239(6) 0.9226(6) 0.4416(5) 0.0275(14) Uani 1 d . . H5A H 0.3836(6) 0.9803(6) 0.4497(5) 0.033 Uiso 1 calc R . H5B H 0.3806(6) 0.8639(6) 0.3899(5) 0.033 Uiso 1 calc R . C6 C 0.2922(7) 0.8626(6) 0.5391(5) 0.031(2) Uani 1 d . . H6A H 0.3863(7) 0.8280(6) 0.5642(5) 0.037 Uiso 1 calc R . H6B H 0.2315(7) 0.9218(6) 0.5891(5) 0.037 Uiso 1 calc R . C7 C 0.3130(7) 0.6599(5) 0.5004(5) 0.0295(15) Uani 1 d . . H7A H 0.3567(7) 0.6214(5) 0.5589(5) 0.035 Uiso 1 calc R . H7B H 0.3943(7) 0.6724(5) 0.4483(5) 0.035 Uiso 1 calc R . C8 C 0.2292(6) 0.5815(5) 0.4590(4) 0.0221(13) Uani 1 d . . H8A H 0.2946(6) 0.5030(5) 0.4407(4) 0.027 Uiso 1 calc R . H8B H 0.1452(6) 0.5709(5) 0.5097(4) 0.027 Uiso 1 calc R . C9 C 0.1044(6) 0.5832(5) 0.3159(4) 0.0172(11) Uani 1 d . . C10 C 0.0364(6) 0.6514(4) 0.2400(4) 0.0168(11) Uani 1 d . . C11 C -0.0405(6) 0.6043(5) 0.1795(4) 0.0182(12) Uani 1 d . . H11A H -0.0862(6) 0.6515(5) 0.1291(4) 0.022 Uiso 1 calc R . C12 C -0.0520(6) 0.4853(5) 0.1921(4) 0.0189(12) Uani 1 d . . C13 C 0.0164(7) 0.4199(5) 0.2677(4) 0.0225(13) Uani 1 d . . H13A H 0.0096(7) 0.3401(5) 0.2772(4) 0.027 Uiso 1 calc R . C14 C 0.0940(7) 0.4673(5) 0.3295(4) 0.0222(13) Uani 1 d . . H14A H 0.1392(7) 0.4206(5) 0.3803(4) 0.027 Uiso 1 calc R . C15 C -0.1305(6) 0.4312(5) 0.1284(4) 0.0193(12) Uani 1 d . . H15A H -0.1362(6) 0.3522(5) 0.1437(4) 0.023 Uiso 1 calc R . C16 C -0.1952(6) 0.4807(5) 0.0510(4) 0.0189(12) Uani 1 d . . H16A H -0.1869(6) 0.5587(5) 0.0335(4) 0.023 Uiso 1 calc R . C17 C -0.2770(6) 0.4256(5) -0.0087(4) 0.0205(12) Uani 1 d . . C18 C -0.4060(7) 0.2945(6) -0.0799(4) 0.0272(14) Uani 1 d . . C19 C -0.4772(7) 0.2124(6) -0.1136(5) 0.034(2) Uani 1 d . . H19A H -0.4750(7) 0.1381(6) -0.0821(5) 0.041 Uiso 1 calc R . C20 C -0.5516(7) 0.2468(6) -0.1964(5) 0.036(2) Uani 1 d . . H20A H -0.6025(7) 0.1945(6) -0.2203(5) 0.043 Uiso 1 calc R . C21 C -0.5537(7) 0.3534(6) -0.2446(5) 0.034(2) Uani 1 d . . H21A H -0.6044(7) 0.3720(6) -0.3010(5) 0.041 Uiso 1 calc R . C22 C -0.4834(6) 0.4333(6) -0.2121(5) 0.0271(14) Uani 1 d . . H22A H -0.4844(6) 0.5063(6) -0.2457(5) 0.032 Uiso 1 calc R . C23 C -0.4099(6) 0.4040(5) -0.1277(4) 0.0239(13) Uani 1 d . . C24 C -0.5280(7) 0.8162(6) -0.2538(5) 0.032(2) Uani 1 d . . C25 C -0.6203(9) 0.9320(7) -0.2264(6) 0.035(2) Uani 1 d . . H25A H -0.7231(80) 0.9273(57) -0.2186(49) 0.037(19) Uiso 1 d . . H25B H -0.5829(81) 0.9742(64) -0.2643(56) 0.037(23) Uiso 1 d . . H25C H -0.6085(85) 0.9672(68) -0.1576(63) 0.063(24) Uiso 1 d . . 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 Ag1 0.0182(2) 0.0219(2) 0.0229(3) 0.0006(2) -0.0028(2) -0.0073(2) Ag2 0.0373(3) 0.0225(3) 0.0332(3) 0.0010(2) -0.0131(2) -0.0023(2) S1 0.0299(9) 0.0248(8) 0.0252(8) -0.0050(6) 0.0017(7) -0.0131(7) O1 0.022(2) 0.011(2) 0.023(2) 0.004(2) -0.011(2) -0.004(2) O2 0.022(2) 0.018(2) 0.021(2) -0.003(2) 0.002(2) -0.009(2) O3 0.019(2) 0.025(2) 0.027(2) -0.004(2) 0.001(2) -0.009(2) O4 0.020(2) 0.027(2) 0.028(2) -0.008(2) -0.003(2) -0.002(2) O5 0.014(2) 0.021(2) 0.016(2) 0.001(2) -0.004(2) -0.002(2) O6 0.022(2) 0.030(2) 0.030(2) 0.008(2) -0.011(2) -0.005(2) O7 0.038(3) 0.028(2) 0.031(3) 0.009(2) -0.010(2) -0.007(2) O8 0.025(3) 0.053(3) 0.045(3) 0.005(2) -0.006(2) -0.023(2) O9 0.038(3) 0.025(2) 0.033(3) -0.004(2) 0.002(2) -0.011(2) O10 0.043(3) 0.025(2) 0.038(3) -0.003(2) -0.006(2) 0.001(2) O11 0.029(3) 0.065(3) 0.028(3) 0.004(2) -0.016(2) -0.013(2) N1 0.015(3) 0.027(3) 0.020(3) -0.008(2) 0.001(2) -0.006(2) N2 0.017(3) 0.025(3) 0.022(3) -0.005(2) 0.000(2) -0.005(2) N3 0.028(3) 0.028(3) 0.016(3) -0.001(2) 0.003(2) -0.008(2) N4 0.045(4) 0.039(3) 0.033(3) 0.000(3) -0.009(3) 0.009(3) C1 0.023(3) 0.010(2) 0.019(3) 0.003(2) -0.005(2) -0.003(2) C2 0.021(3) 0.017(3) 0.021(3) 0.005(2) 0.003(2) -0.005(2) C3 0.030(4) 0.014(3) 0.026(3) 0.000(2) 0.004(3) -0.009(2) C4 0.028(4) 0.026(3) 0.034(4) -0.006(3) 0.003(3) -0.016(3) C5 0.017(3) 0.036(4) 0.033(4) -0.012(3) -0.005(3) -0.009(3) C6 0.022(3) 0.041(4) 0.031(4) -0.017(3) -0.004(3) -0.010(3) C7 0.028(4) 0.033(4) 0.026(3) -0.005(3) -0.013(3) 0.002(3) C8 0.022(3) 0.028(3) 0.013(3) 0.007(2) -0.007(2) 0.004(2) C9 0.016(3) 0.020(3) 0.013(3) -0.004(2) 0.001(2) 0.000(2) C10 0.023(3) 0.013(3) 0.014(3) -0.002(2) 0.003(2) -0.005(2) C11 0.020(3) 0.019(3) 0.017(3) -0.001(2) -0.005(2) -0.004(2) C12 0.017(3) 0.017(3) 0.022(3) -0.002(2) 0.003(2) -0.006(2) C13 0.030(3) 0.007(2) 0.029(3) 0.003(2) -0.004(3) -0.004(2) C14 0.028(3) 0.016(3) 0.020(3) 0.001(2) -0.005(3) 0.001(2) C15 0.023(3) 0.014(3) 0.022(3) -0.002(2) -0.002(2) -0.009(2) C16 0.021(3) 0.016(3) 0.021(3) -0.004(2) 0.004(2) -0.012(2) C17 0.016(3) 0.025(3) 0.021(3) -0.005(2) 0.002(2) -0.009(2) C18 0.022(3) 0.039(4) 0.021(3) -0.012(3) 0.006(3) -0.011(3) C19 0.024(4) 0.036(4) 0.041(4) -0.024(3) 0.013(3) -0.013(3) C20 0.026(4) 0.049(4) 0.034(4) -0.031(3) 0.010(3) -0.017(3) C21 0.018(3) 0.057(5) 0.025(3) -0.020(3) 0.006(3) -0.009(3) C22 0.020(3) 0.036(4) 0.024(3) -0.011(3) 0.007(3) -0.010(3) C23 0.015(3) 0.035(3) 0.019(3) -0.009(3) 0.004(2) -0.003(3) C24 0.028(4) 0.043(4) 0.024(3) -0.001(3) -0.006(3) -0.002(3) C25 0.033(4) 0.034(4) 0.037(4) -0.001(3) -0.009(3) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 O6 2.367(4) . ? Ag1 O3 2.426(4) . ? Ag1 O2 2.607(4) . ? Ag1 O4 2.659(4) . ? Ag1 O1 2.690(4) . ? Ag1 O5 2.721(4) . ? Ag1 O3 3.061(4) 2_576 ? Ag2 N1 2.236(5) . ? Ag2 O11 2.406(5) . ? Ag2 N4 2.462(5) . ? S1 C18 1.732(6) . ? S1 C17 1.767(6) . ? O1 C10 1.362(6) . ? O1 C1 1.439(6) . ? O2 C3 1.426(6) . ? O2 C2 1.430(6) . ? O3 C4 1.438(7) . ? O3 C5 1.448(7) . ? O4 C7 1.426(7) . ? O4 C6 1.441(7) . ? O5 C9 1.366(6) . ? O5 C8 1.433(6) . ? O6 N2 1.258(6) . ? O7 N2 1.252(6) . ? O8 N2 1.232(6) . ? O9 N3 1.234(6) . ? O10 N3 1.257(6) . ? O11 N3 1.278(6) . ? N1 C17 1.304(7) . ? N1 C23 1.401(7) . ? N4 C24 1.146(8) . ? C1 C2 1.501(7) . ? C3 C4 1.512(9) . ? C5 C6 1.490(9) . ? C7 C8 1.509(8) . ? C9 C14 1.381(8) . ? C9 C10 1.413(7) . ? C10 C11 1.374(7) . ? C11 C12 1.419(7) . ? C12 C13 1.398(8) . ? C12 C15 1.458(7) . ? C13 C14 1.392(8) . ? C15 C16 1.335(8) . ? C16 C17 1.452(7) . ? C18 C23 1.407(9) . ? C18 C19 1.413(8) . ? C19 C20 1.404(10) . ? C20 C21 1.382(10) . ? C21 C22 1.379(8) . ? C22 C23 1.412(8) . ? C24 C25 1.446(10) . ? 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 O6 Ag1 O3 155.39(14) . . ? O6 Ag1 O2 132.73(12) . . ? O3 Ag1 O2 69.30(12) . . ? O6 Ag1 O4 91.29(13) . . ? O3 Ag1 O4 69.12(13) . . ? O2 Ag1 O4 135.69(13) . . ? O6 Ag1 O1 96.92(13) . . ? O3 Ag1 O1 104.53(12) . . ? O2 Ag1 O1 63.43(11) . . ? O4 Ag1 O1 114.09(11) . . ? O6 Ag1 O5 77.61(13) . . ? O3 Ag1 O5 104.31(12) . . ? O2 Ag1 O5 115.36(11) . . ? O4 Ag1 O5 62.22(11) . . ? O1 Ag1 O5 56.38(10) . . ? O6 Ag1 O3 77.09(13) . 2_576 ? O3 Ag1 O3 88.79(12) . 2_576 ? O2 Ag1 O3 100.86(11) . 2_576 ? O4 Ag1 O3 92.90(11) . 2_576 ? O1 Ag1 O3 152.62(11) . 2_576 ? O5 Ag1 O3 143.77(11) . 2_576 ? N1 Ag2 O11 138.8(2) . . ? N1 Ag2 N4 111.3(2) . . ? O11 Ag2 N4 81.6(2) . . ? C18 S1 C17 89.4(3) . . ? C10 O1 C1 117.4(4) . . ? C10 O1 Ag1 109.8(3) . . ? C1 O1 Ag1 110.0(3) . . ? C3 O2 C2 114.4(4) . . ? C3 O2 Ag1 106.1(3) . . ? C2 O2 Ag1 116.7(3) . . ? C4 O3 C5 111.5(4) . . ? C4 O3 Ag1 115.0(3) . . ? C5 O3 Ag1 113.8(3) . . ? C7 O4 C6 113.0(5) . . ? C7 O4 Ag1 117.6(3) . . ? C6 O4 Ag1 105.6(3) . . ? C9 O5 C8 118.3(4) . . ? C9 O5 Ag1 108.7(3) . . ? C8 O5 Ag1 111.2(3) . . ? N2 O6 Ag1 102.4(3) . . ? N3 O11 Ag2 102.8(4) . . ? C17 N1 C23 111.3(5) . . ? C17 N1 Ag2 122.3(4) . . ? C23 N1 Ag2 126.0(4) . . ? O8 N2 O7 121.7(5) . . ? O8 N2 O6 119.9(5) . . ? O7 N2 O6 118.4(5) . . ? O9 N3 O10 121.5(5) . . ? O9 N3 O11 121.4(5) . . ? O10 N3 O11 117.0(5) . . ? C24 N4 Ag2 114.1(5) . . ? O1 C1 C2 105.9(4) . . ? O2 C2 C1 109.2(4) . . ? O2 C3 C4 112.5(4) . . ? O3 C4 C3 107.8(5) . . ? O3 C5 C6 108.6(5) . . ? O4 C6 C5 112.7(5) . . ? O4 C7 C8 109.7(5) . . ? O5 C8 C7 106.4(5) . . ? O5 C9 C14 124.6(5) . . ? O5 C9 C10 115.7(5) . . ? C14 C9 C10 119.7(5) . . ? O1 C10 C11 125.2(5) . . ? O1 C10 C9 113.8(4) . . ? C11 C10 C9 121.0(5) . . ? C10 C11 C12 120.1(5) . . ? C13 C12 C11 117.7(5) . . ? C13 C12 C15 120.4(5) . . ? C11 C12 C15 121.9(5) . . ? C12 C13 C14 122.4(5) . . ? C9 C14 C13 119.1(5) . . ? C16 C15 C12 127.1(5) . . ? C15 C16 C17 125.6(5) . . ? N1 C17 C16 123.5(5) . . ? N1 C17 S1 114.9(4) . . ? C16 C17 S1 121.5(4) . . ? C23 C18 C19 121.1(6) . . ? C23 C18 S1 109.8(4) . . ? C19 C18 S1 129.1(5) . . ? C20 C19 C18 116.3(6) . . ? C21 C20 C19 122.8(6) . . ? C20 C21 C22 121.0(6) . . ? C21 C22 C23 118.4(6) . . ? N1 C23 C18 114.6(5) . . ? N1 C23 C22 125.0(6) . . ? C18 C23 C22 120.4(5) . . ? N4 C24 C25 178.1(8) . . ? _refine_diff_density_max 1.120 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.155