Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_dqzhang _database_code_CSD 172993 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Ding, Liang' 'Fang, Decai' 'Hu, Huiming' 'Huang, Yuanhe' 'Xu, Wei' 'Zhang, Deqing' 'Zhu, Dao B.' _publ_contact_author_name Prof Deqing Zhang'' _publ_contact_author_address ; Prof Deqing Zhang Organic Solid Laboratory Institute of Chemcistry, Chinese Academy of Sciences Beijing 100080, China Beijing 100080 CHINA ; _publ_contact_author_email 'DQZHANG@INFOC3.ICAS.AC.CN' _publ_section_title ; The first 1D silver(I) complex of nitronyl nitroxide with strong spin-spin interaction through silver (I) ion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 Ag N5 O8' _chemical_formula_weight 481.20 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' '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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.278(6) _cell_length_b 7.0410(14) _cell_length_c 18.894(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.55(3) _cell_angle_gamma 90.00 _cell_volume 3474.3(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) cell_measurement_reflns_used 16047 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.48 _exptl_crystal_description ,Block' _exptl_crystal_colour 'Black' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.840 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 1.216 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.8805 _exptl_absorpt_correction_T_max 1.1038 _exptl_special_details ; ABSCOR by T.Higashi 8 March, 1995 ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method 'Oscillation' _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3956 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3956 _reflns_number_gt 3400 _reflns_threshold_expression >2sigma(I) computing_data_collection ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _computing_cell_refinement ; Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381 USA. ; _computing_data_reduction ; Sheldrick, G. M. (1997) SHELXS97, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_solution ; Sheldrick, G. M. (1997) SHELXS97, Program for the Solution of Crystal Structure, University of Gottingen, Germany. ; _computing_structure_refinement ; Sheldrick, G. M. (1997) SHELXL97, Program for the Refinement of Crystal Structure, University of Gottingen, Germany. ; _computing_molecular_graphics ; Interactive Molecular Graphics XP, Virsion 4.2 for MSDOS (1990), Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _computing_publication_material ; Sheldrick, G. M. (1997) SHELXL97, Program for the refinement of Crystal Structure, University of Gottingen, Germany. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+12.3141P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3956 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Ag1 Ag 0.144847(8) 0.85933(3) 0.071491(11) 0.01837(8) Uani 1 1 d . . . N1 N 0.11405(8) 1.2261(3) 0.15288(12) 0.0127(4) Uani 1 1 d . . . N2 N 0.08256(8) 1.5028(3) 0.10439(12) 0.0130(4) Uani 1 1 d . . . N3 N 0.24943(8) 1.3930(3) 0.11154(12) 0.0145(4) Uani 1 1 d . . . N11 N 0.25563(9) 0.8597(3) 0.16147(13) 0.0182(5) Uani 1 1 d . . . N21 N 0.10447(8) 1.0828(3) -0.06813(12) 0.0181(5) Uani 1 1 d . . . O1 O 0.14278(7) 1.0788(3) 0.17057(10) 0.0163(4) Uani 1 1 d . . . O2 O 0.07624(7) 1.6632(3) 0.06960(11) 0.0182(4) Uani 1 1 d . . . O11 O 0.23415(8) 0.9509(3) 0.09966(11) 0.0265(5) Uani 1 1 d . . . O12 O 0.22897(8) 0.7581(3) 0.18598(12) 0.0234(4) Uani 1 1 d . . . O13 O 0.30254(8) 0.8731(3) 0.19690(14) 0.0330(5) Uani 1 1 d . . . O21 O 0.13543(8) 0.9472(3) -0.06034(12) 0.0278(5) Uani 1 1 d . . . O22 O 0.08684(8) 1.1082(3) -0.01690(11) 0.0218(4) Uani 1 1 d . . . O23 O 0.09241(9) 1.1887(3) -0.12430(12) 0.0282(5) Uani 1 1 d . . . C1 C 0.16074(10) 1.4027(4) 0.08497(14) 0.0127(5) Uani 1 1 d . . . C2 C 0.21045(10) 1.3573(4) 0.13334(14) 0.0139(5) Uani 1 1 d . . . H2A H 0.2167 1.3021 0.1808 0.017 Uiso 1 1 calc R . . C3 C 0.24168(10) 1.4680(4) 0.04240(15) 0.0172(5) Uani 1 1 d . . . H3A H 0.2695 1.4903 0.0288 0.021 Uiso 1 1 calc R . . C4 C 0.19302(10) 1.5119(4) -0.00832(15) 0.0186(5) Uani 1 1 d . . . H4A H 0.1878 1.5614 -0.0564 0.022 Uiso 1 1 calc R . . C5 C 0.15171(10) 1.4811(4) 0.01335(14) 0.0157(5) Uani 1 1 d . . . H5A H 0.1186 1.5126 -0.0196 0.019 Uiso 1 1 calc R . . C6 C 0.30208(10) 1.3533(4) 0.16654(16) 0.0200(6) Uani 1 1 d . . . H6A H 0.3008 1.3008 0.2127 0.030 Uiso 1 1 calc R . . H6B H 0.3214 1.4692 0.1783 0.030 Uiso 1 1 calc R . . H6C H 0.3181 1.2642 0.1443 0.030 Uiso 1 1 calc R . . C7 C 0.11957(9) 1.3759(4) 0.11275(14) 0.0131(5) Uani 1 1 d . . . C8 C 0.05265(9) 1.4533(4) 0.15273(14) 0.0142(5) Uani 1 1 d . . . C9 C 0.06505(9) 1.2372(4) 0.16657(14) 0.0142(5) Uani 1 1 d . . . C10 C -0.00356(10) 1.4995(4) 0.10978(16) 0.0209(6) Uani 1 1 d . . . H10A H -0.0078 1.6346 0.1037 0.031 Uiso 1 1 calc R . . H10B H -0.0229 1.4530 0.1382 0.031 Uiso 1 1 calc R . . H10C H -0.0155 1.4403 0.0602 0.031 Uiso 1 1 calc R . . C11 C 0.07562(11) 1.5750(4) 0.22482(15) 0.0213(6) Uani 1 1 d . . . H11A H 0.0665 1.7056 0.2122 0.032 Uiso 1 1 calc R . . H11B H 0.1122 1.5624 0.2454 0.032 Uiso 1 1 calc R . . H11C H 0.0626 1.5334 0.2622 0.032 Uiso 1 1 calc R . . C12 C 0.02698(10) 1.1079(4) 0.10615(16) 0.0210(6) Uani 1 1 d . . . H12A H 0.0369 0.9777 0.1181 0.032 Uiso 1 1 calc R . . H12B H 0.0269 1.1381 0.0566 0.032 Uiso 1 1 calc R . . H12C H -0.0067 1.1270 0.1059 0.032 Uiso 1 1 calc R . . C13 C 0.07489(11) 1.1688(4) 0.24718(16) 0.0205(6) Uani 1 1 d . . . H13A H 0.0822 1.0352 0.2508 0.031 Uiso 1 1 calc R . . H13B H 0.0451 1.1919 0.2586 0.031 Uiso 1 1 calc R . . H13C H 0.1036 1.2361 0.2831 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 Ag1 0.01850(11) 0.01786(12) 0.01853(11) 0.00106(8) 0.00686(8) -0.00025(8) N1 0.0110(10) 0.0126(10) 0.0135(9) -0.0008(8) 0.0036(8) 0.0012(8) N2 0.0138(10) 0.0112(10) 0.0136(9) 0.0003(8) 0.0046(8) 0.0006(8) N3 0.0120(10) 0.0153(11) 0.0158(10) -0.0017(8) 0.0049(8) 0.0007(8) N11 0.0205(11) 0.0169(11) 0.0177(11) -0.0011(9) 0.0080(9) 0.0026(9) N21 0.0161(11) 0.0211(11) 0.0150(10) -0.0019(9) 0.0038(8) -0.0007(9) O1 0.0188(9) 0.0138(9) 0.0153(8) 0.0018(7) 0.0056(7) 0.0045(7) O2 0.0183(9) 0.0128(9) 0.0225(9) 0.0050(8) 0.0068(8) 0.0024(7) O11 0.0269(11) 0.0352(12) 0.0166(9) 0.0076(9) 0.0074(8) 0.0058(10) O12 0.0274(11) 0.0209(10) 0.0241(10) 0.0000(9) 0.0124(8) -0.0047(9) O13 0.0163(10) 0.0395(14) 0.0367(12) 0.0099(11) 0.0030(9) 0.0003(9) O21 0.0311(11) 0.0287(12) 0.0254(10) 0.0056(9) 0.0130(9) 0.0120(10) O22 0.0232(10) 0.0275(11) 0.0181(9) -0.0030(8) 0.0117(8) -0.0020(8) O23 0.0348(12) 0.0318(12) 0.0204(10) 0.0091(9) 0.0132(9) 0.0119(10) C1 0.0142(11) 0.0122(11) 0.0132(11) -0.0010(9) 0.0068(9) -0.0019(9) C2 0.0145(11) 0.0135(12) 0.0137(11) -0.0017(10) 0.0054(9) -0.0003(9) C3 0.0167(12) 0.0190(13) 0.0187(12) -0.0007(10) 0.0100(10) -0.0005(10) C4 0.0210(13) 0.0198(13) 0.0164(12) 0.0024(11) 0.0089(10) 0.0010(11) C5 0.0149(12) 0.0168(12) 0.0146(11) -0.0002(10) 0.0047(9) 0.0007(10) C6 0.0115(11) 0.0281(15) 0.0194(12) 0.0011(11) 0.0048(10) -0.0002(11) C7 0.0115(11) 0.0147(12) 0.0120(11) -0.0008(9) 0.0033(9) 0.0001(9) C8 0.0131(11) 0.0160(12) 0.0137(11) 0.0000(10) 0.0055(9) 0.0021(10) C9 0.0110(11) 0.0157(12) 0.0164(12) -0.0004(10) 0.0058(9) -0.0003(9) C10 0.0123(12) 0.0272(15) 0.0231(13) 0.0031(12) 0.0068(10) 0.0044(11) C11 0.0263(14) 0.0193(13) 0.0176(12) -0.0052(11) 0.0077(11) 0.0013(12) C12 0.0158(12) 0.0209(14) 0.0247(14) -0.0042(11) 0.0060(11) -0.0047(11) C13 0.0223(13) 0.0239(14) 0.0189(13) 0.0052(11) 0.0118(11) 0.0014(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 O2 2.3706(19) 1_545 ? Ag1 O1 2.4452(19) . ? Ag1 O11 2.459(2) . ? Ag1 O21 2.480(2) . ? Ag1 O22 2.540(2) . ? N1 O1 1.281(3) . ? N1 C7 1.342(3) . ? N1 C9 1.506(3) . ? N2 O2 1.284(3) . ? N2 C7 1.339(3) . ? N2 C8 1.504(3) . ? N3 C2 1.340(3) . ? N3 C3 1.347(3) . ? N3 C6 1.479(3) . ? N11 O13 1.239(3) . ? N11 O12 1.250(3) . ? N11 O11 1.265(3) . ? N21 O23 1.234(3) . ? N21 O22 1.260(3) . ? N21 O21 1.265(3) . ? O2 Ag1 2.3707(19) 1_565 ? C1 C2 1.389(4) . ? C1 C5 1.392(3) . ? C1 C7 1.461(3) . ? C3 C4 1.377(4) . ? C4 C5 1.395(4) . ? C8 C10 1.517(3) . ? C8 C11 1.527(4) . ? C8 C9 1.561(4) . ? C9 C13 1.518(4) . ? C9 C12 1.532(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 O2 Ag1 O1 96.89(7) 1_545 . ? O2 Ag1 O11 157.33(7) 1_545 . ? O1 Ag1 O11 89.58(7) . . ? O2 Ag1 O21 110.99(8) 1_545 . ? O1 Ag1 O21 125.91(7) . . ? O11 Ag1 O21 81.82(8) . . ? O2 Ag1 O22 94.23(7) 1_545 . ? O1 Ag1 O22 82.43(6) . . ? O11 Ag1 O22 108.19(7) . . ? O21 Ag1 O22 51.23(7) . . ? O1 N1 C7 125.7(2) . . ? O1 N1 C9 122.0(2) . . ? C7 N1 C9 111.8(2) . . ? O2 N2 C7 126.6(2) . . ? O2 N2 C8 120.9(2) . . ? C7 N2 C8 111.7(2) . . ? C2 N3 C3 121.6(2) . . ? C2 N3 C6 118.3(2) . . ? C3 N3 C6 120.1(2) . . ? O13 N11 O12 121.1(2) . . ? O13 N11 O11 119.7(2) . . ? O12 N11 O11 119.2(2) . . ? O23 N21 O22 121.0(2) . . ? O23 N21 O21 120.5(2) . . ? O22 N21 O21 118.6(2) . . ? N1 O1 Ag1 120.74(14) . . ? N2 O2 Ag1 123.51(15) . 1_565 ? N11 O11 Ag1 99.00(16) . . ? N21 O21 Ag1 96.21(15) . . ? N21 O22 Ag1 93.49(15) . . ? C2 C1 C5 119.6(2) . . ? C2 C1 C7 118.6(2) . . ? C5 C1 C7 121.7(2) . . ? N3 C2 C1 119.9(2) . . ? N3 C3 C4 120.7(2) . . ? C3 C4 C5 119.1(2) . . ? C1 C5 C4 119.0(2) . . ? N2 C7 N1 109.6(2) . . ? N2 C7 C1 124.5(2) . . ? N1 C7 C1 125.9(2) . . ? N2 C8 C10 110.1(2) . . ? N2 C8 C11 105.4(2) . . ? C10 C8 C11 110.9(2) . . ? N2 C8 C9 100.66(19) . . ? C10 C8 C9 114.9(2) . . ? C11 C8 C9 114.0(2) . . ? N1 C9 C13 109.2(2) . . ? N1 C9 C12 105.7(2) . . ? C13 C9 C12 111.4(2) . . ? N1 C9 C8 100.60(19) . . ? C13 C9 C8 114.8(2) . . ? C12 C9 C8 113.9(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.888 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.111