# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Nikolay Gerasimchuk' 'N. Kent Dalley' 'Andrey N. Esaulenko' 'Curtis Moore' _publ_contact_author_name 'Nikolay Gerasimchuk' _publ_contact_author_email NNGERASIMCHUK@MISSOURISTATE.EDU _publ_section_title ; 2-Cyano-2-isonitroso acetamide and its Ag(I) complexes. Silver(I) cyanoximate as nonelectric gas sensor. ; # Attachment 'ACO-system-CIFs-combined1.cif' data_HACO-1 _database_code_depnum_ccdc_archive 'CCDC 743057' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Cyan-2-isonitrosoacetamide ; _chemical_name_common 'Amide-cyanoxime, HACO' _chemical_melting_point '449 K' _chemical_formula_moiety 'C3 H3 N3 O2' _chemical_formula_sum 'C6 H6 N6 O4' _chemical_formula_weight 226.17 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.0010(17) _cell_length_b 6.3458(16) _cell_length_c 21.804(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.119(17) _cell_angle_gamma 90.00 _cell_volume 956.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 697 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 25.09 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _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 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 2186 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1689 _reflns_number_gt 1203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0484P)^2^+0.2635P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1689 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 C1A C 0.7477(3) 0.1553(4) 0.68247(9) 0.0315(5) Uani 1 1 d . . . C2A C 0.8204(4) 0.0549(4) 0.74064(11) 0.0399(6) Uani 1 1 d . . . C3A C 0.6522(3) 0.3650(4) 0.68284(10) 0.0347(5) Uani 1 1 d . . . C1B C 0.7479(3) 0.9534(3) 0.43071(9) 0.0313(5) Uani 1 1 d . . . C2B C 0.6811(3) 1.1160(4) 0.46789(10) 0.0367(5) Uani 1 1 d . . . C3B C 0.8495(3) 0.7661(3) 0.46148(9) 0.0330(5) Uani 1 1 d . . . N1A N 0.7573(3) 0.0729(3) 0.62970(8) 0.0365(5) Uani 1 1 d . . . N2A N 0.8773(3) -0.0251(4) 0.78622(10) 0.0583(7) Uani 1 1 d . . . N3A N 0.5985(3) 0.4542(3) 0.62842(9) 0.0451(5) Uani 1 1 d . . . H31A H 0.6160 0.3937 0.5898 0.054 Uiso 1 1 d R . . H32A H 0.5284 0.5913 0.6298 0.054 Uiso 1 1 d R . . N1B N 0.7299(3) 0.9659(3) 0.37153(8) 0.0359(5) Uani 1 1 d . . . N2B N 0.6259(3) 1.2492(4) 0.49532(9) 0.0534(6) Uani 1 1 d . . . N3B N 0.9012(3) 0.6203(3) 0.42483(8) 0.0415(5) Uani 1 1 d . . . H31B H 0.8667 0.6299 0.3802 0.050 Uiso 1 1 d R . . H32B H 0.9691 0.5050 0.4403 0.050 Uiso 1 1 d R . . O1A O 0.8406(3) -0.1203(3) 0.63339(8) 0.0479(5) Uani 1 1 d . . . H1A H 0.8470 -0.1641 0.5903 0.057 Uiso 1 1 d R . . O2A O 0.6249(3) 0.4446(3) 0.73207(7) 0.0488(5) Uani 1 1 d . . . O1B O 0.6430(2) 1.1440(3) 0.34771(7) 0.0430(4) Uani 1 1 d . . . H1B H 0.6395 1.1256 0.2997 0.052 Uiso 1 1 d R . . O2B O 0.8817(2) 0.7560(3) 0.51884(7) 0.0429(4) Uani 1 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 C1A 0.0368(12) 0.0304(12) 0.0270(11) -0.0002(9) 0.0042(8) -0.0010(10) C2A 0.0480(14) 0.0396(14) 0.0319(12) 0.0008(11) 0.0063(10) 0.0049(12) C3A 0.0412(12) 0.0298(12) 0.0318(12) -0.0013(10) 0.0021(9) -0.0053(10) C1B 0.0351(12) 0.0311(12) 0.0273(11) -0.0003(9) 0.0037(8) -0.0006(10) C2B 0.0436(13) 0.0353(13) 0.0310(12) 0.0062(10) 0.0049(10) 0.0044(11) C3B 0.0373(12) 0.0323(12) 0.0290(11) 0.0002(10) 0.0042(9) 0.0007(10) N1A 0.0430(11) 0.0324(11) 0.0344(10) -0.0014(8) 0.0075(8) -0.0010(9) N2A 0.0748(16) 0.0586(16) 0.0399(12) 0.0093(11) 0.0043(11) 0.0173(13) N3A 0.0676(14) 0.0335(12) 0.0321(10) 0.0012(8) 0.0011(9) 0.0085(10) N1B 0.0427(11) 0.0326(11) 0.0315(10) 0.0041(8) 0.0031(8) 0.0010(9) N2B 0.0718(16) 0.0447(13) 0.0444(12) 0.0008(11) 0.0119(11) 0.0163(12) N3B 0.0575(13) 0.0352(11) 0.0307(10) -0.0019(9) 0.0031(9) 0.0116(10) O1A 0.0663(12) 0.0372(10) 0.0420(9) -0.0034(8) 0.0143(8) 0.0105(9) O2A 0.0722(13) 0.0419(11) 0.0327(9) -0.0049(8) 0.0093(8) 0.0084(9) O1B 0.0592(10) 0.0379(10) 0.0321(8) 0.0099(7) 0.0076(7) 0.0074(9) O2B 0.0585(10) 0.0435(10) 0.0256(8) 0.0008(7) 0.0037(7) 0.0159(8) _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 C1A N1A 1.275(3) . ? C1A C2A 1.439(3) . ? C1A C3A 1.490(3) . ? C2A N2A 1.131(3) . ? C3A O2A 1.228(3) . ? C3A N3A 1.314(3) . ? C1B N1B 1.279(3) . ? C1B C2B 1.436(3) . ? C1B C3B 1.489(3) . ? C2B N2B 1.138(3) . ? C3B O2B 1.237(2) . ? C3B N3B 1.310(3) . ? N1A O1A 1.355(2) . ? N3A H31A 0.9515 . ? N3A H32A 1.0019 . ? N1B O1B 1.348(2) . ? N3B H31B 0.9671 . ? N3B H32B 0.9075 . ? O1A H1A 0.9881 . ? O1B H1B 1.0489 . ? 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 N1A C1A C2A 123.5(2) . . ? N1A C1A C3A 117.32(19) . . ? C2A C1A C3A 119.17(19) . . ? N2A C2A C1A 179.6(3) . . ? O2A C3A N3A 123.4(2) . . ? O2A C3A C1A 120.26(19) . . ? N3A C3A C1A 116.3(2) . . ? N1B C1B C2B 122.4(2) . . ? N1B C1B C3B 117.90(19) . . ? C2B C1B C3B 119.63(18) . . ? N2B C2B C1B 177.4(2) . . ? O2B C3B N3B 123.8(2) . . ? O2B C3B C1B 119.64(19) . . ? N3B C3B C1B 116.57(19) . . ? C1A N1A O1A 113.66(18) . . ? C3A N3A H31A 124.6 . . ? C3A N3A H32A 114.7 . . ? H31A N3A H32A 120.6 . . ? C1B N1B O1B 114.03(18) . . ? C3B N3B H31B 121.3 . . ? C3B N3B H32B 121.5 . . ? H31B N3B H32B 117.2 . . ? N1A O1A H1A 106.4 . . ? N1B O1B H1B 103.2 . . ? 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 N1A C1A C2A N2A -33(45) . . . . ? C3A C1A C2A N2A 146(45) . . . . ? N1A C1A C3A O2A 174.2(2) . . . . ? C2A C1A C3A O2A -4.6(3) . . . . ? N1A C1A C3A N3A -4.9(3) . . . . ? C2A C1A C3A N3A 176.3(2) . . . . ? N1B C1B C3B O2B 174.9(2) . . . . ? C2B C1B C3B O2B -2.7(3) . . . . ? N1B C1B C3B N3B -4.6(3) . . . . ? C2B C1B C3B N3B 177.9(2) . . . . ? C2A C1A N1A O1A 0.8(3) . . . . ? C3A C1A N1A O1A -178.00(18) . . . . ? C2B C1B N1B O1B -0.1(3) . . . . ? C3B C1B N1B O1B -177.56(18) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.152 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.042 #===END data_msu1 _database_code_depnum_ccdc_archive 'CCDC 743058' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Silver(I) 2-cyano-2-isonitroso-acetamide ; _chemical_name_common Ag(ACO) _chemical_melting_point 'decomposes upon heating to 146 C' _chemical_formula_moiety 'C3 H2 Ag N3 O2' _chemical_formula_sum 'C3 H2 Ag N3 O2' _chemical_formula_weight 219.95 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.735(3) _cell_length_b 6.8313(15) _cell_length_c 6.3756(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.654(3) _cell_angle_gamma 90.00 _cell_volume 508.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1472 _cell_measurement_theta_min 3.49 _cell_measurement_theta_max 31.88 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 3.869 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.4659 _exptl_absorpt_correction_T_max 0.7816 _exptl_absorpt_process_details twinabs _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 120(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 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 996 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.99 _reflns_number_total 996 _reflns_number_gt 928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0340P)^2^+1.9825P] 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_number_reflns 996 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.209 _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 Ag1 Ag -0.03509(3) 0.76381(5) 0.09800(7) 0.01139(15) Uani 1 1 d . . . C1 C 0.2378(4) 0.7834(7) 0.1854(8) 0.0089(10) Uani 1 1 d . . . C2 C 0.2147(4) 0.5698(8) 0.1798(9) 0.0110(11) Uani 1 1 d . . . C3 C 0.3516(4) 0.8632(7) 0.2134(8) 0.0120(11) Uani 1 1 d . . . N1 N 0.1488(4) 0.9004(6) 0.1653(7) 0.0123(9) Uani 1 1 d . . . N2 N 0.3024(4) 0.4475(6) 0.2030(8) 0.0138(10) Uani 1 1 d . . . H2A H 0.2907 0.3232 0.2003 0.017 Uiso 1 1 calc R . . H2B H 0.3712 0.4923 0.2208 0.017 Uiso 1 1 calc R . . N3 N 0.4429(4) 0.9263(7) 0.2364(8) 0.0206(11) Uani 1 1 d . . . O1 O 0.1667(3) 1.0893(5) 0.1716(6) 0.0127(8) Uani 1 1 d . . . O2 O 0.1135(3) 0.5109(5) 0.1537(6) 0.0118(8) Uani 1 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 0.0091(2) 0.0086(2) 0.0161(2) -0.00065(15) -0.00028(17) 0.00058(14) C1 0.007(2) 0.009(2) 0.010(3) 0.0006(19) 0.0023(19) -0.0025(18) C2 0.012(3) 0.011(2) 0.010(3) -0.0003(19) 0.001(2) -0.0023(19) C3 0.014(3) 0.008(2) 0.014(3) -0.0010(19) 0.003(2) 0.001(2) N1 0.015(2) 0.009(2) 0.012(2) 0.0009(17) -0.0018(18) -0.0028(17) N2 0.013(2) 0.0069(19) 0.021(3) -0.0002(17) -0.0014(19) -0.0026(17) N3 0.018(3) 0.014(2) 0.029(3) -0.0006(19) 0.002(2) 0.000(2) O1 0.0157(19) 0.0061(16) 0.016(2) -0.0007(14) 0.0005(16) -0.0001(14) O2 0.0130(18) 0.0074(15) 0.015(2) 0.0003(14) 0.0013(16) 0.0004(14) _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 N1 2.352(5) . ? Ag1 O1 2.414(4) 3_575 ? Ag1 O2 2.455(4) . ? Ag1 O1 2.532(4) 2_545 ? Ag1 O2 2.547(4) 2 ? Ag1 O2 2.579(4) 3_565 ? Ag1 Ag1 3.1934(8) 4_576 ? Ag1 Ag1 3.1934(8) 4_575 ? C1 N1 1.311(7) . ? C1 C3 1.437(7) . ? C1 C2 1.484(7) . ? C2 O2 1.250(6) . ? C2 N2 1.323(7) . ? C3 N3 1.151(7) . ? N1 O1 1.307(5) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? O1 Ag1 2.414(4) 3_575 ? O1 Ag1 2.532(4) 2 ? O2 Ag1 2.547(4) 2_545 ? O2 Ag1 2.579(4) 3_565 ? 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 Ag1 O1 118.45(14) . 3_575 ? N1 Ag1 O2 68.11(14) . . ? O1 Ag1 O2 142.29(12) 3_575 . ? N1 Ag1 O1 133.03(15) . 2_545 ? O1 Ag1 O1 102.98(15) 3_575 2_545 ? O2 Ag1 O1 92.86(12) . 2_545 ? N1 Ag1 O2 90.26(14) . 2 ? O1 Ag1 O2 85.54(12) 3_575 2 ? O2 Ag1 O2 132.15(5) . 2 ? O1 Ag1 O2 70.93(12) 2_545 2 ? N1 Ag1 O2 131.82(14) . 3_565 ? O1 Ag1 O2 72.27(12) 3_575 3_565 ? O2 Ag1 O2 77.43(13) . 3_565 ? O1 Ag1 O2 79.50(13) 2_545 3_565 ? O2 Ag1 O2 137.77(16) 2 3_565 ? N1 Ag1 Ag1 86.08(11) . 4_576 ? O1 Ag1 Ag1 132.27(9) 3_575 4_576 ? O2 Ag1 Ag1 83.33(9) . 4_576 ? O1 Ag1 Ag1 48.18(9) 2_545 4_576 ? O2 Ag1 Ag1 51.92(8) 2 4_576 ? O2 Ag1 Ag1 122.89(8) 3_565 4_576 ? N1 Ag1 Ag1 96.62(11) . 4_575 ? O1 Ag1 Ag1 51.43(9) 3_575 4_575 ? O2 Ag1 Ag1 91.89(9) . 4_575 ? O1 Ag1 Ag1 127.68(9) 2_545 4_575 ? O2 Ag1 Ag1 134.04(8) 2 4_575 ? O2 Ag1 Ag1 51.02(8) 3_565 4_575 ? Ag1 Ag1 Ag1 173.22(2) 4_576 4_575 ? N1 C1 C3 120.2(4) . . ? N1 C1 C2 117.1(4) . . ? C3 C1 C2 122.7(4) . . ? O2 C2 N2 122.0(5) . . ? O2 C2 C1 119.3(4) . . ? N2 C2 C1 118.7(5) . . ? N3 C3 C1 179.7(6) . . ? O1 N1 C1 118.3(4) . . ? O1 N1 Ag1 122.6(3) . . ? C1 N1 Ag1 118.9(3) . . ? C2 N2 H2A 120.0 . . ? C2 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 O1 Ag1 107.4(3) . 3_575 ? N1 O1 Ag1 112.1(3) . 2 ? Ag1 O1 Ag1 80.39(11) 3_575 2 ? C2 O2 Ag1 116.4(3) . . ? C2 O2 Ag1 121.8(3) . 2_545 ? Ag1 O2 Ag1 105.16(13) . 2_545 ? C2 O2 Ag1 126.4(3) . 3_565 ? Ag1 O2 Ag1 102.57(13) . 3_565 ? Ag1 O2 Ag1 77.06(10) 2_545 3_565 ? 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 N1 C1 C2 O2 1.0(8) . . . . ? C3 C1 C2 O2 -179.6(5) . . . . ? N1 C1 C2 N2 -178.9(5) . . . . ? C3 C1 C2 N2 0.5(8) . . . . ? N1 C1 C3 N3 149(100) . . . . ? C2 C1 C3 N3 -30(100) . . . . ? C3 C1 N1 O1 0.0(8) . . . . ? C2 C1 N1 O1 179.4(5) . . . . ? C3 C1 N1 Ag1 176.1(4) . . . . ? C2 C1 N1 Ag1 -4.5(7) . . . . ? O1 Ag1 N1 O1 41.4(5) 3_575 . . . ? O2 Ag1 N1 O1 -179.9(4) . . . . ? O1 Ag1 N1 O1 -107.4(4) 2_545 . . . ? O2 Ag1 N1 O1 -43.7(4) 2 . . . ? O2 Ag1 N1 O1 132.5(4) 3_565 . . . ? Ag1 Ag1 N1 O1 -95.5(4) 4_576 . . . ? Ag1 Ag1 N1 O1 90.8(4) 4_575 . . . ? O1 Ag1 N1 C1 -134.6(4) 3_575 . . . ? O2 Ag1 N1 C1 4.2(4) . . . . ? O1 Ag1 N1 C1 76.6(4) 2_545 . . . ? O2 Ag1 N1 C1 140.3(4) 2 . . . ? O2 Ag1 N1 C1 -43.4(5) 3_565 . . . ? Ag1 Ag1 N1 C1 88.5(4) 4_576 . . . ? Ag1 Ag1 N1 C1 -85.2(4) 4_575 . . . ? C1 N1 O1 Ag1 138.5(4) . . . 3_575 ? Ag1 N1 O1 Ag1 -37.5(4) . . . 3_575 ? C1 N1 O1 Ag1 -135.0(4) . . . 2 ? Ag1 N1 O1 Ag1 49.0(4) . . . 2 ? N2 C2 O2 Ag1 -177.3(4) . . . . ? C1 C2 O2 Ag1 2.8(6) . . . . ? N2 C2 O2 Ag1 52.1(7) . . . 2_545 ? C1 C2 O2 Ag1 -127.9(4) . . . 2_545 ? N2 C2 O2 Ag1 -45.4(7) . . . 3_565 ? C1 C2 O2 Ag1 134.6(4) . . . 3_565 ? N1 Ag1 O2 C2 -3.6(4) . . . . ? O1 Ag1 O2 C2 105.1(4) 3_575 . . . ? O1 Ag1 O2 C2 -139.3(4) 2_545 . . . ? O2 Ag1 O2 C2 -72.6(4) 2 . . . ? O2 Ag1 O2 C2 142.1(4) 3_565 . . . ? Ag1 Ag1 O2 C2 -92.0(4) 4_576 . . . ? Ag1 Ag1 O2 C2 92.8(4) 4_575 . . . ? N1 Ag1 O2 Ag1 134.53(18) . . . 2_545 ? O1 Ag1 O2 Ag1 -116.82(18) 3_575 . . 2_545 ? O1 Ag1 O2 Ag1 -1.21(14) 2_545 . . 2_545 ? O2 Ag1 O2 Ag1 65.5(2) 2 . . 2_545 ? O2 Ag1 O2 Ag1 -79.79(13) 3_565 . . 2_545 ? Ag1 Ag1 O2 Ag1 46.10(10) 4_576 . . 2_545 ? Ag1 Ag1 O2 Ag1 -129.09(11) 4_575 . . 2_545 ? N1 Ag1 O2 Ag1 -145.68(18) . . . 3_565 ? O1 Ag1 O2 Ag1 -37.0(2) 3_575 . . 3_565 ? O1 Ag1 O2 Ag1 78.58(14) 2_545 . . 3_565 ? O2 Ag1 O2 Ag1 145.24(14) 2 . . 3_565 ? O2 Ag1 O2 Ag1 0.0 3_565 . . 3_565 ? Ag1 Ag1 O2 Ag1 125.88(11) 4_576 . . 3_565 ? Ag1 Ag1 O2 Ag1 -49.30(11) 4_575 . . 3_565 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.047 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.171 #===END data_centro _database_code_depnum_ccdc_archive 'CCDC 743059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2-picolinate) of silver(I) 2-cyan-2-isonitrosoacetamide ; _chemical_name_common Silver(I)amidecyanoximate-bis(2-picolinate) _chemical_melting_point 'decomposes upon heating to 110 C' _chemical_formula_moiety 'C15 H16 Ag N5 O2' _chemical_formula_sum 'C15 H16 Ag N5 O2' _chemical_formula_weight 406.20 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.394(6) _cell_length_b 10.771(9) _cell_length_c 11.252(9) _cell_angle_alpha 90.187(9) _cell_angle_beta 106.037(8) _cell_angle_gamma 107.492(9) _cell_volume 817.8(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 203 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.11 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 1.249 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6016 _exptl_absorpt_correction_T_max 0.6364 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 296(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 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 8518 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3323 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0210P)^2^+0.5404P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0061(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3323 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0569 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.24204(3) 0.907627(17) 0.120591(16) 0.05330(9) Uani 1 1 d . . . C1 C 0.1567(3) 0.69186(19) 0.31196(18) 0.0370(4) Uani 1 1 d . . . C2 C 0.1875(3) 0.6029(2) 0.40435(19) 0.0391(4) Uani 1 1 d . . . C3 C -0.0337(3) 0.7195(2) 0.26871(19) 0.0408(4) Uani 1 1 d . . . C4 C 0.2929(3) 1.1607(2) 0.3011(2) 0.0490(5) Uani 1 1 d . . . C5 C 0.3311(4) 1.2916(3) 0.3346(3) 0.0642(7) Uani 1 1 d . . . C6 C 0.3416(5) 1.3794(3) 0.2469(4) 0.0750(9) Uani 1 1 d . . . C7 C 0.3097(5) 1.3354(3) 0.1272(3) 0.0724(8) Uani 1 1 d . . . C8 C 0.2702(4) 1.2042(3) 0.0992(2) 0.0579(6) Uani 1 1 d . . . C9 C 0.2815(6) 1.0624(4) 0.3945(3) 0.0714(8) Uani 1 1 d . . . C10 C 0.2206(3) 0.7486(2) -0.1306(2) 0.0481(5) Uani 1 1 d . . . C11 C 0.2070(4) 0.7284(3) -0.2550(3) 0.0620(7) Uani 1 1 d . . . C12 C 0.2271(4) 0.8308(3) -0.3268(3) 0.0637(7) Uani 1 1 d . . . C13 C 0.2615(4) 0.9533(3) -0.2739(2) 0.0596(6) Uani 1 1 d . . . C14 C 0.2735(4) 0.9671(3) -0.1510(2) 0.0562(6) Uani 1 1 d . . . C15 C 0.2026(7) 0.6390(3) -0.0494(4) 0.0780(10) Uani 1 1 d . . . H5 H 0.355(5) 1.318(3) 0.419(3) 0.081(10) Uiso 1 1 d . . . H6 H 0.370(5) 1.462(4) 0.268(3) 0.099(12) Uiso 1 1 d . . . H7 H 0.313(5) 1.386(3) 0.060(3) 0.091(11) Uiso 1 1 d . . . H8 H 0.247(4) 1.175(3) 0.018(3) 0.072(9) Uiso 1 1 d . . . H11 H 0.186(5) 0.647(3) -0.283(3) 0.075(9) Uiso 1 1 d . . . H12 H 0.215(5) 0.822(3) -0.411(3) 0.080(9) Uiso 1 1 d . . . H13 H 0.276(4) 1.026(3) -0.317(3) 0.076(9) Uiso 1 1 d . . . H14 H 0.297(5) 1.048(3) -0.116(3) 0.078(9) Uiso 1 1 d . . . H9A H 0.331(6) 1.106(4) 0.469(4) 0.123(15) Uiso 1 1 d . . . H15A H 0.114(6) 0.632(4) -0.011(4) 0.102(14) Uiso 1 1 d . . . H9B H 0.360(6) 1.014(4) 0.395(4) 0.110(14) Uiso 1 1 d . . . H15B H 0.323(6) 0.656(4) 0.017(4) 0.102(14) Uiso 1 1 d . . . H9C H 0.150(6) 1.004(4) 0.381(3) 0.103(13) Uiso 1 1 d . . . H15C H 0.190(6) 0.564(4) -0.090(4) 0.118(14) Uiso 1 1 d . . . H1N3 H -0.272(4) 0.682(3) 0.307(3) 0.060(8) Uiso 1 1 d . . . H2N3 H -0.152(3) 0.616(2) 0.383(2) 0.041(6) Uiso 1 1 d . . . N1 N 0.3017(3) 0.75349(18) 0.26548(17) 0.0443(4) Uani 1 1 d . . . N2 N 0.2081(3) 0.5318(2) 0.4772(2) 0.0571(5) Uani 1 1 d . . . N3 N -0.1707(3) 0.6646(2) 0.3254(2) 0.0574(6) Uani 1 1 d . . . N4 N 0.2640(3) 1.11692(18) 0.18346(17) 0.0461(4) Uani 1 1 d . . . N5 N 0.2516(3) 0.86766(18) -0.07844(17) 0.0469(4) Uani 1 1 d . . . O1 O 0.4664(2) 0.72948(18) 0.30453(18) 0.0606(5) Uani 1 1 d . . . O2 O -0.0633(2) 0.79061(18) 0.18519(16) 0.0577(4) Uani 1 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 0.07360(15) 0.04796(12) 0.05002(12) 0.01604(8) 0.03231(9) 0.02272(9) C1 0.0419(10) 0.0373(10) 0.0373(10) 0.0087(8) 0.0157(8) 0.0164(8) C2 0.0402(10) 0.0416(10) 0.0410(10) 0.0079(9) 0.0139(8) 0.0187(9) C3 0.0422(11) 0.0442(11) 0.0407(10) 0.0113(9) 0.0133(9) 0.0187(9) C4 0.0457(12) 0.0586(14) 0.0443(12) 0.0007(10) 0.0104(9) 0.0214(10) C5 0.0599(15) 0.0652(17) 0.0680(17) -0.0152(14) 0.0199(13) 0.0194(13) C6 0.0752(19) 0.0485(15) 0.112(3) -0.0040(17) 0.0410(18) 0.0218(14) C7 0.090(2) 0.0582(16) 0.092(2) 0.0283(16) 0.0432(18) 0.0411(15) C8 0.0783(17) 0.0584(15) 0.0486(13) 0.0147(11) 0.0197(12) 0.0369(13) C9 0.094(2) 0.084(2) 0.0419(14) 0.0118(14) 0.0197(15) 0.037(2) C10 0.0497(12) 0.0417(11) 0.0541(13) 0.0056(10) 0.0203(10) 0.0114(9) C11 0.0665(16) 0.0538(15) 0.0596(15) -0.0111(12) 0.0203(13) 0.0083(12) C12 0.0676(16) 0.0802(19) 0.0421(13) 0.0025(13) 0.0184(12) 0.0191(14) C13 0.0730(17) 0.0677(17) 0.0510(14) 0.0220(12) 0.0289(12) 0.0304(14) C14 0.0828(18) 0.0474(13) 0.0538(14) 0.0145(11) 0.0339(13) 0.0298(13) C15 0.116(3) 0.0445(15) 0.083(2) 0.0163(15) 0.047(2) 0.0221(17) N1 0.0441(10) 0.0481(10) 0.0501(10) 0.0126(8) 0.0206(8) 0.0217(8) N2 0.0621(12) 0.0623(13) 0.0589(12) 0.0275(10) 0.0236(10) 0.0310(10) N3 0.0470(11) 0.0727(14) 0.0712(14) 0.0397(12) 0.0306(10) 0.0330(11) N4 0.0538(11) 0.0473(10) 0.0398(9) 0.0053(8) 0.0098(8) 0.0229(8) N5 0.0602(11) 0.0428(10) 0.0463(10) 0.0093(8) 0.0253(9) 0.0194(8) O1 0.0459(9) 0.0661(11) 0.0861(13) 0.0268(9) 0.0304(9) 0.0305(8) O2 0.0557(9) 0.0717(11) 0.0564(10) 0.0370(9) 0.0206(8) 0.0309(8) _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 N5 2.303(3) . ? Ag1 N4 2.305(3) . ? Ag1 N1 2.381(2) . ? Ag1 O2 2.533(2) . ? C1 N1 1.322(3) . ? C1 C2 1.435(3) . ? C1 C3 1.477(3) . ? C2 N2 1.134(3) . ? C3 O2 1.229(3) . ? C3 N3 1.335(3) . ? C4 N4 1.342(3) . ? C4 C5 1.381(4) . ? C4 C9 1.494(4) . ? C5 C6 1.371(5) . ? C5 H5 0.94(3) . ? C6 C7 1.359(5) . ? C6 H6 0.87(4) . ? C7 C8 1.371(4) . ? C7 H7 0.94(4) . ? C8 N4 1.338(3) . ? C8 H8 0.92(3) . ? C9 H9A 0.89(5) . ? C9 H9B 0.88(4) . ? C9 H9C 0.96(4) . ? C10 N5 1.337(3) . ? C10 C11 1.386(4) . ? C10 C15 1.493(4) . ? C11 C12 1.365(4) . ? C11 H11 0.88(3) . ? C12 C13 1.367(4) . ? C12 H12 0.93(3) . ? C13 C14 1.366(4) . ? C13 H13 0.92(3) . ? C14 N5 1.347(3) . ? C14 H14 0.90(3) . ? C15 H15A 0.86(4) . ? C15 H15B 0.96(4) . ? C15 H15C 0.90(5) . ? N1 O1 1.279(2) . ? N3 H1N3 0.79(3) . ? N3 H2N3 0.84(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 N5 Ag1 N4 117.67(6) . . ? N5 Ag1 N1 118.08(8) . . ? N4 Ag1 N1 121.93(8) . . ? N5 Ag1 O2 120.14(7) . . ? N4 Ag1 O2 96.85(7) . . ? N1 Ag1 O2 67.98(7) . . ? N1 C1 C2 120.07(18) . . ? N1 C1 C3 118.44(18) . . ? C2 C1 C3 121.47(18) . . ? N2 C2 C1 178.7(2) . . ? O2 C3 N3 121.8(2) . . ? O2 C3 C1 121.35(19) . . ? N3 C3 C1 116.86(19) . . ? N4 C4 C5 121.2(2) . . ? N4 C4 C9 117.5(2) . . ? C5 C4 C9 121.3(3) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 122(2) . . ? C4 C5 H5 118(2) . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120(3) . . ? C5 C6 H6 120(3) . . ? C6 C7 C8 118.4(3) . . ? C6 C7 H7 127(2) . . ? C8 C7 H7 115(2) . . ? N4 C8 C7 123.7(3) . . ? N4 C8 H8 118.2(19) . . ? C7 C8 H8 118.2(19) . . ? C4 C9 H9A 107(3) . . ? C4 C9 H9B 113(3) . . ? H9A C9 H9B 103(4) . . ? C4 C9 H9C 112(2) . . ? H9A C9 H9C 113(4) . . ? H9B C9 H9C 108(4) . . ? N5 C10 C11 121.2(2) . . ? N5 C10 C15 117.2(2) . . ? C11 C10 C15 121.6(3) . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 124(2) . . ? C10 C11 H11 116(2) . . ? C11 C12 C13 118.9(3) . . ? C11 C12 H12 124(2) . . ? C13 C12 H12 117(2) . . ? C14 C13 C12 118.0(3) . . ? C14 C13 H13 119(2) . . ? C12 C13 H13 123(2) . . ? N5 C14 C13 124.3(3) . . ? N5 C14 H14 118(2) . . ? C13 C14 H14 118(2) . . ? C10 C15 H15A 114(3) . . ? C10 C15 H15B 110(2) . . ? H15A C15 H15B 103(3) . . ? C10 C15 H15C 112(3) . . ? H15A C15 H15C 113(4) . . ? H15B C15 H15C 104(3) . . ? O1 N1 C1 117.80(18) . . ? O1 N1 Ag1 124.52(13) . . ? C1 N1 Ag1 117.64(14) . . ? C3 N3 H1N3 119(2) . . ? C3 N3 H2N3 122.7(17) . . ? H1N3 N3 H2N3 118(3) . . ? C8 N4 C4 117.6(2) . . ? C8 N4 Ag1 117.37(17) . . ? C4 N4 Ag1 124.55(15) . . ? C10 N5 C14 117.2(2) . . ? C10 N5 Ag1 123.70(15) . . ? C14 N5 Ag1 118.90(16) . . ? C3 O2 Ag1 114.00(14) . . ? 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 N1 C1 C3 O2 5.2(3) . . . . ? C2 C1 C3 O2 -176.3(2) . . . . ? N1 C1 C3 N3 -174.2(2) . . . . ? C2 C1 C3 N3 4.3(3) . . . . ? N4 C4 C5 C6 -0.5(4) . . . . ? C9 C4 C5 C6 179.7(3) . . . . ? C4 C5 C6 C7 1.5(5) . . . . ? C5 C6 C7 C8 -0.7(5) . . . . ? C6 C7 C8 N4 -1.0(5) . . . . ? N5 C10 C11 C12 0.6(4) . . . . ? C15 C10 C11 C12 -179.0(3) . . . . ? C10 C11 C12 C13 0.3(4) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 N5 -0.7(4) . . . . ? C2 C1 N1 O1 0.9(3) . . . . ? C3 C1 N1 O1 179.42(19) . . . . ? C2 C1 N1 Ag1 -176.84(14) . . . . ? C3 C1 N1 Ag1 1.7(2) . . . . ? N5 Ag1 N1 O1 64.97(19) . . . . ? N4 Ag1 N1 O1 -97.33(18) . . . . ? O2 Ag1 N1 O1 178.43(19) . . . . ? N5 Ag1 N1 C1 -117.49(16) . . . . ? N4 Ag1 N1 C1 80.21(17) . . . . ? O2 Ag1 N1 C1 -4.03(15) . . . . ? C7 C8 N4 C4 1.9(4) . . . . ? C7 C8 N4 Ag1 -170.9(2) . . . . ? C5 C4 N4 C8 -1.1(3) . . . . ? C9 C4 N4 C8 178.7(3) . . . . ? C5 C4 N4 Ag1 171.16(18) . . . . ? C9 C4 N4 Ag1 -9.0(3) . . . . ? N5 Ag1 N4 C8 3.7(2) . . . . ? N1 Ag1 N4 C8 166.03(17) . . . . ? O2 Ag1 N4 C8 -125.70(19) . . . . ? N5 Ag1 N4 C4 -168.64(17) . . . . ? N1 Ag1 N4 C4 -6.3(2) . . . . ? O2 Ag1 N4 C4 62.01(19) . . . . ? C11 C10 N5 C14 -1.5(4) . . . . ? C15 C10 N5 C14 178.2(3) . . . . ? C11 C10 N5 Ag1 172.96(19) . . . . ? C15 C10 N5 Ag1 -7.4(3) . . . . ? C13 C14 N5 C10 1.5(4) . . . . ? C13 C14 N5 Ag1 -173.2(2) . . . . ? N4 Ag1 N5 C10 -173.07(17) . . . . ? N1 Ag1 N5 C10 23.9(2) . . . . ? O2 Ag1 N5 C10 -55.7(2) . . . . ? N4 Ag1 N5 C14 1.3(2) . . . . ? N1 Ag1 N5 C14 -161.79(18) . . . . ? O2 Ag1 N5 C14 118.67(19) . . . . ? N3 C3 O2 Ag1 170.75(19) . . . . ? C1 C3 O2 Ag1 -8.6(3) . . . . ? N5 Ag1 O2 C3 117.26(17) . . . . ? N4 Ag1 O2 C3 -115.10(17) . . . . ? N1 Ag1 O2 C3 6.63(16) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.858 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.047 #===END data_Ag-N4-ACO1 _database_code_depnum_ccdc_archive 'CCDC 743060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Silver(I)-ane[N4]-macrocyclic complex' _chemical_melting_point 'decomposes upon heating to 147 C' _chemical_formula_moiety 'C15 H26 Ag N4, C3 H2 N3 O2, C2 H3 N' _chemical_formula_sum 'C20 H31 Ag N8 O2' _chemical_formula_weight 523.40 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.604(2) _cell_length_b 11.354(2) _cell_length_c 17.447(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.800(10) _cell_angle_gamma 90.00 _cell_volume 2413.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 235 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 25.06 _exptl_crystal_description block _exptl_crystal_colour orange-brown _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.867 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _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 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 4476 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.06 _reflns_number_total 4268 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0346P)^2^+1.8285P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef none _refine_ls_number_reflns 4268 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 Ag Ag 0.20270(3) 0.10685(3) 0.15759(2) 0.04185(15) Uani 1 1 d . . . N1 N 0.1686(3) 0.2157(3) 0.0416(2) 0.0365(9) Uani 1 1 d . . . C2 C 0.2478(4) 0.2312(4) 0.0040(3) 0.0402(11) Uani 1 1 d . . . C3 C 0.2329(4) 0.3039(5) -0.0608(3) 0.0536(14) Uani 1 1 d . . . H3 H 0.2884 0.3136 -0.0865 0.064 Uiso 1 1 calc R . . C4 C 0.1349(5) 0.3621(5) -0.0869(3) 0.0679(17) Uani 1 1 d . . . H4 H 0.1230 0.4104 -0.1314 0.081 Uiso 1 1 calc R . . C5 C 0.0542(4) 0.3488(5) -0.0472(3) 0.0554(14) Uani 1 1 d . . . H5 H -0.0122 0.3887 -0.0638 0.066 Uiso 1 1 calc R . . C6 C 0.0737(4) 0.2756(4) 0.0173(3) 0.0408(11) Uani 1 1 d . . . C7 C -0.0085(4) 0.2535(4) 0.0659(3) 0.0430(12) Uani 1 1 d . . . H7 H -0.0633 0.3167 0.0550 0.052 Uiso 1 1 calc R . . C8 C -0.0672(4) 0.1360(5) 0.0433(4) 0.0629(16) Uani 1 1 d G . . H8A H -0.1160 0.1273 0.0772 0.094 Uiso 1 1 calc G . . H8B H -0.1088 0.1340 -0.0111 0.094 Uiso 1 1 calc G . . H8C H -0.0149 0.0729 0.0530 0.094 Uiso 1 1 calc G . . N9 N 0.0472(3) 0.2551(3) 0.1504(2) 0.0356(9) Uani 1 1 d . . . H9 H 0.0100 0.2080 0.1761 0.043 Uiso 1 1 d R . . C10 C 0.0730(4) 0.3738(4) 0.1820(3) 0.0446(12) Uani 1 1 d . . . H10A H 0.0057 0.4192 0.1727 0.053 Uiso 1 1 calc R . . H10B H 0.1206 0.4118 0.1538 0.053 Uiso 1 1 calc R . . C11 C 0.1286(4) 0.3744(4) 0.2700(3) 0.0484(13) Uani 1 1 d . . . H11A H 0.1207 0.4522 0.2908 0.058 Uiso 1 1 calc R . . H11B H 0.0906 0.3193 0.2962 0.058 Uiso 1 1 calc R . . C12 C 0.2488(4) 0.3429(4) 0.2911(3) 0.0418(11) Uani 1 1 d . . . H12A H 0.2720 0.3222 0.3469 0.050 Uiso 1 1 calc R . . H12B H 0.2596 0.2745 0.2607 0.050 Uiso 1 1 calc R . . N13 N 0.3171(3) 0.4403(3) 0.2753(2) 0.0354(8) Uani 1 1 d . . . H13 H 0.2980 0.4604 0.2197 0.043 Uiso 1 1 d R . . C14 C 0.4345(4) 0.4076(4) 0.2860(3) 0.0461(12) Uani 1 1 d . . . H14A H 0.4682 0.3993 0.3423 0.055 Uiso 1 1 calc R . . H14B H 0.4712 0.4720 0.2667 0.055 Uiso 1 1 calc R . . C15 C 0.4548(4) 0.2945(4) 0.2444(3) 0.0481(13) Uani 1 1 d . . . H15A H 0.5333 0.2815 0.2557 0.058 Uiso 1 1 calc R . . H15B H 0.4235 0.2291 0.2669 0.058 Uiso 1 1 calc R . . C16 C 0.4084(4) 0.2928(4) 0.1556(3) 0.0406(11) Uani 1 1 d . . . H16A H 0.3423 0.3403 0.1418 0.049 Uiso 1 1 calc R . . H16B H 0.4612 0.3273 0.1303 0.049 Uiso 1 1 calc R . . N17 N 0.3825(3) 0.1724(3) 0.1256(2) 0.0336(8) Uani 1 1 d . . . H17 H 0.4630 0.1431 0.1462 0.040 Uiso 1 1 d R . . C18 C 0.3543(4) 0.1660(4) 0.0388(3) 0.0409(11) Uani 1 1 d . . . H18 H 0.4133 0.2020 0.0195 0.049 Uiso 1 1 calc R . . C19 C 0.3432(5) 0.0351(5) 0.0145(3) 0.0600(15) Uani 1 1 d G . . H19A H 0.4091 -0.0069 0.0395 0.090 Uiso 1 1 calc G . . H19B H 0.2822 0.0010 0.0300 0.090 Uiso 1 1 calc G . . H19C H 0.3308 0.0302 -0.0420 0.090 Uiso 1 1 calc G . . O21 O 0.8993(3) 0.1812(3) 0.2483(2) 0.0604(10) Uani 1 1 d . . . N22 N 0.8366(3) 0.0930(4) 0.2530(3) 0.0503(10) Uani 1 1 d . . . C23 C 0.7363(4) 0.0939(4) 0.2055(3) 0.0429(11) Uani 1 1 d . . . C24 C 0.6959(4) 0.1841(5) 0.1485(3) 0.0511(12) Uani 1 1 d . . . N25 N 0.6635(5) 0.2564(5) 0.1031(3) 0.0817(16) Uani 1 1 d . . . C26 C 0.6616(4) -0.0052(4) 0.2083(3) 0.0486(12) Uani 1 1 d . . . O27 O 0.5678(3) -0.0060(3) 0.1656(2) 0.0681(11) Uani 1 1 d . . . N28 N 0.7019(4) -0.0904(4) 0.2582(3) 0.0840(17) Uani 1 1 d . . . H28A H 0.6681 -0.1446 0.2722 0.126 Uiso 1 1 d R . . H28B H 0.7723 -0.0798 0.2825 0.126 Uiso 1 1 d R . . C31 C 0.0602(6) 0.1295(8) 0.4265(4) 0.118(3) Uani 1 1 d . . . H31A H 0.0645 0.1670 0.4764 0.176 Uiso 1 1 d R . . H31B H 0.0265 0.0535 0.4257 0.176 Uiso 1 1 d R . . H31C H 0.0171 0.1771 0.3845 0.176 Uiso 1 1 d R . . C32 C 0.1636(6) 0.1021(6) 0.4100(4) 0.0718(17) Uani 1 1 d . . . N33 N 0.2421(6) 0.0798(5) 0.3945(4) 0.0912(18) Uani 1 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 Ag 0.0492(2) 0.03313(19) 0.0429(2) 0.00858(19) 0.01107(15) 0.0019(2) N1 0.033(2) 0.042(2) 0.034(2) 0.0074(17) 0.0098(17) 0.0075(18) C2 0.037(3) 0.049(3) 0.034(2) -0.002(2) 0.007(2) 0.001(2) C3 0.053(3) 0.071(4) 0.041(3) 0.011(3) 0.019(2) -0.002(3) C4 0.074(4) 0.079(4) 0.048(3) 0.032(3) 0.012(3) 0.009(3) C5 0.051(3) 0.062(3) 0.046(3) 0.010(3) 0.001(3) 0.012(3) C6 0.039(3) 0.044(3) 0.035(2) 0.003(2) 0.001(2) 0.004(2) C7 0.024(2) 0.055(3) 0.047(3) 0.003(2) 0.005(2) 0.008(2) C8 0.046(3) 0.080(4) 0.062(3) -0.017(3) 0.013(3) -0.016(3) N9 0.033(2) 0.0300(19) 0.043(2) 0.0023(17) 0.0091(17) -0.0012(17) C10 0.033(2) 0.033(3) 0.068(3) -0.002(2) 0.013(2) 0.001(2) C11 0.050(3) 0.042(3) 0.059(3) -0.017(2) 0.024(2) -0.012(2) C12 0.045(3) 0.036(2) 0.043(3) -0.004(2) 0.009(2) -0.005(2) N13 0.037(2) 0.0341(19) 0.035(2) -0.0056(16) 0.0097(17) -0.0056(17) C14 0.038(3) 0.050(3) 0.048(3) -0.015(2) 0.006(2) -0.001(2) C15 0.035(3) 0.055(3) 0.050(3) -0.010(2) 0.002(2) 0.009(2) C16 0.043(3) 0.033(2) 0.046(3) -0.002(2) 0.013(2) 0.004(2) N17 0.030(2) 0.034(2) 0.036(2) -0.0046(17) 0.0080(16) 0.0030(17) C18 0.037(3) 0.051(3) 0.039(3) -0.002(2) 0.018(2) 0.002(2) C19 0.056(4) 0.057(4) 0.064(4) -0.020(3) 0.011(3) 0.009(3) O21 0.042(2) 0.057(2) 0.084(3) 0.001(2) 0.0201(19) -0.0095(19) N22 0.037(2) 0.048(3) 0.068(3) -0.003(2) 0.016(2) -0.001(2) C23 0.040(3) 0.037(3) 0.052(3) -0.001(2) 0.012(2) 0.004(2) C24 0.051(3) 0.050(3) 0.052(3) -0.006(3) 0.013(3) -0.005(3) N25 0.102(4) 0.064(3) 0.068(3) 0.018(3) 0.002(3) 0.003(3) C26 0.037(3) 0.046(3) 0.065(3) 0.002(3) 0.017(3) -0.002(2) O27 0.036(2) 0.064(3) 0.096(3) 0.012(2) 0.002(2) -0.0038(19) N28 0.056(3) 0.063(3) 0.122(4) 0.039(3) 0.003(3) -0.006(3) C31 0.087(5) 0.192(10) 0.073(5) -0.028(6) 0.020(4) 0.001(6) C32 0.087(5) 0.062(4) 0.067(4) -0.008(3) 0.021(4) -0.004(4) N33 0.109(5) 0.068(4) 0.105(5) -0.004(3) 0.043(4) 0.003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag N13 2.271(3) 2_545 ? Ag N1 2.317(3) . ? Ag N9 2.562(3) . ? Ag N17 2.578(3) . ? N1 C2 1.337(5) . ? N1 C6 1.347(5) . ? C2 C3 1.374(6) . ? C2 C18 1.518(6) . ? C3 C4 1.371(7) . ? C3 H3 0.9300 . ? C4 C5 1.379(7) . ? C4 H4 0.9300 . ? C5 C6 1.369(6) . ? C5 H5 0.9300 . ? C6 C7 1.518(6) . ? C7 N9 1.463(6) . ? C7 C8 1.528(7) . ? C7 H7 0.9800 . ? C8 H8A 0.9604 . ? C8 H8B 0.9598 . ? C8 H8C 0.9599 . ? N9 C10 1.461(5) . ? N9 H9 0.9013 . ? C10 C11 1.516(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.508(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N13 1.470(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N13 C14 1.490(6) . ? N13 Ag 2.271(3) 2 ? N13 H13 0.9646 . ? C14 C15 1.529(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.510(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N17 1.470(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N17 C18 1.467(5) . ? N17 H17 1.0412 . ? C18 C19 1.542(7) . ? C18 H18 0.9800 . ? C19 H19A 0.9599 . ? C19 H19B 0.9600 . ? C19 H19C 0.9596 . ? O21 N22 1.291(5) . ? N22 C23 1.323(6) . ? C23 C24 1.426(7) . ? C23 C26 1.476(7) . ? C24 N25 1.142(6) . ? C26 O27 1.226(6) . ? C26 N28 1.313(6) . ? N28 H28A 0.8215 . ? N28 H28B 0.8879 . ? C31 C32 1.439(10) . ? C31 H31A 0.9590 . ? C31 H31B 0.9598 . ? C31 H31C 0.9598 . ? C32 N33 1.120(8) . ? 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 N13 Ag N1 150.98(13) 2_545 . ? N13 Ag N9 112.87(12) 2_545 . ? N1 Ag N9 68.78(12) . . ? N13 Ag N17 124.77(12) 2_545 . ? N1 Ag N17 68.54(12) . . ? N9 Ag N17 120.24(11) . . ? C2 N1 C6 119.6(4) . . ? C2 N1 Ag 120.2(3) . . ? C6 N1 Ag 119.7(3) . . ? N1 C2 C3 121.3(4) . . ? N1 C2 C18 115.8(4) . . ? C3 C2 C18 122.9(4) . . ? C4 C3 C2 119.1(5) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.8(5) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 118.7(5) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? N1 C6 C5 121.6(5) . . ? N1 C6 C7 114.8(4) . . ? C5 C6 C7 123.7(4) . . ? N9 C7 C6 109.9(4) . . ? N9 C7 C8 110.3(4) . . ? C6 C7 C8 110.8(4) . . ? N9 C7 H7 108.6 . . ? C6 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C7 C8 H8A 106.0 . . ? C7 C8 H8B 112.4 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.9 . . ? H8A C8 H8C 109.4 . . ? H8B C8 H8C 109.5 . . ? C10 N9 C7 113.3(4) . . ? C10 N9 Ag 119.6(3) . . ? C7 N9 Ag 101.9(3) . . ? C10 N9 H9 117.0 . . ? C7 N9 H9 108.5 . . ? Ag N9 H9 94.3 . . ? N9 C10 C11 112.8(4) . . ? N9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 114.9(4) . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? N13 C12 C11 112.0(4) . . ? N13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? N13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 N13 C14 113.5(4) . . ? C12 N13 Ag 112.5(3) . 2 ? C14 N13 Ag 112.3(3) . 2 ? C12 N13 H13 111.1 . . ? C14 N13 H13 99.7 . . ? Ag N13 H13 106.8 2 . ? N13 C14 C15 115.5(4) . . ? N13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? N13 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 115.5(4) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? N17 C16 C15 111.6(4) . . ? N17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? N17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C18 N17 C16 112.7(4) . . ? C18 N17 Ag 102.4(2) . . ? C16 N17 Ag 108.6(3) . . ? C18 N17 H17 107.3 . . ? C16 N17 H17 93.8 . . ? Ag N17 H17 131.9 . . ? N17 C18 C2 110.2(3) . . ? N17 C18 C19 108.2(4) . . ? C2 C18 C19 110.6(4) . . ? N17 C18 H18 109.3 . . ? C2 C18 H18 109.3 . . ? C19 C18 H18 109.3 . . ? C18 C19 H19A 110.3 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 108.6 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O21 N22 C23 117.2(4) . . ? N22 C23 C24 123.8(5) . . ? N22 C23 C26 119.3(4) . . ? C24 C23 C26 116.9(4) . . ? N25 C24 C23 179.8(7) . . ? O27 C26 N28 123.2(5) . . ? O27 C26 C23 120.6(5) . . ? N28 C26 C23 116.2(5) . . ? C26 N28 H28A 127.4 . . ? C26 N28 H28B 112.8 . . ? H28A N28 H28B 119.3 . . ? C32 C31 H31A 115.8 . . ? C32 C31 H31B 102.9 . . ? H31A C31 H31B 109.4 . . ? C32 C31 H31C 109.5 . . ? H31A C31 H31C 109.4 . . ? H31B C31 H31C 109.5 . . ? N33 C32 C31 177.5(8) . . ? 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 N13 Ag N1 C2 -106.1(4) 2_545 . . . ? N9 Ag N1 C2 154.8(4) . . . . ? N17 Ag N1 C2 17.6(3) . . . . ? N13 Ag N1 C6 82.3(4) 2_545 . . . ? N9 Ag N1 C6 -16.9(3) . . . . ? N17 Ag N1 C6 -154.1(4) . . . . ? C6 N1 C2 C3 -2.4(7) . . . . ? Ag N1 C2 C3 -174.1(4) . . . . ? C6 N1 C2 C18 176.2(4) . . . . ? Ag N1 C2 C18 4.6(5) . . . . ? N1 C2 C3 C4 0.4(8) . . . . ? C18 C2 C3 C4 -178.2(5) . . . . ? C2 C3 C4 C5 1.3(9) . . . . ? C3 C4 C5 C6 -1.0(9) . . . . ? C2 N1 C6 C5 2.7(7) . . . . ? Ag N1 C6 C5 174.4(4) . . . . ? C2 N1 C6 C7 -178.3(4) . . . . ? Ag N1 C6 C7 -6.6(5) . . . . ? C4 C5 C6 N1 -1.0(8) . . . . ? C4 C5 C6 C7 -179.9(5) . . . . ? N1 C6 C7 N9 44.1(5) . . . . ? C5 C6 C7 N9 -136.9(5) . . . . ? N1 C6 C7 C8 -78.0(5) . . . . ? C5 C6 C7 C8 100.9(6) . . . . ? C6 C7 N9 C10 77.0(5) . . . . ? C8 C7 N9 C10 -160.5(4) . . . . ? C6 C7 N9 Ag -52.7(4) . . . . ? C8 C7 N9 Ag 69.8(4) . . . . ? N13 Ag N9 C10 122.0(3) 2_545 . . . ? N1 Ag N9 C10 -89.3(3) . . . . ? N17 Ag N9 C10 -42.2(4) . . . . ? N13 Ag N9 C7 -112.3(3) 2_545 . . . ? N1 Ag N9 C7 36.4(3) . . . . ? N17 Ag N9 C7 83.5(3) . . . . ? C7 N9 C10 C11 178.8(4) . . . . ? Ag N9 C10 C11 -61.1(5) . . . . ? N9 C10 C11 C12 77.8(5) . . . . ? C10 C11 C12 N13 76.0(5) . . . . ? C11 C12 N13 C14 -172.9(4) . . . . ? C11 C12 N13 Ag 58.2(4) . . . 2 ? C12 N13 C14 C15 49.4(5) . . . . ? Ag N13 C14 C15 178.5(3) 2 . . . ? N13 C14 C15 C16 58.8(6) . . . . ? C14 C15 C16 N17 -152.2(4) . . . . ? C15 C16 N17 C18 -170.7(4) . . . . ? C15 C16 N17 Ag 76.6(4) . . . . ? N13 Ag N17 C18 115.0(3) 2_545 . . . ? N1 Ag N17 C18 -35.5(3) . . . . ? N9 Ag N17 C18 -82.7(3) . . . . ? N13 Ag N17 C16 -125.6(3) 2_545 . . . ? N1 Ag N17 C16 83.9(3) . . . . ? N9 Ag N17 C16 36.7(3) . . . . ? C16 N17 C18 C2 -66.1(5) . . . . ? Ag N17 C18 C2 50.4(4) . . . . ? C16 N17 C18 C19 172.9(4) . . . . ? Ag N17 C18 C19 -70.6(4) . . . . ? N1 C2 C18 N17 -41.3(6) . . . . ? C3 C2 C18 N17 137.3(5) . . . . ? N1 C2 C18 C19 78.3(5) . . . . ? C3 C2 C18 C19 -103.1(6) . . . . ? O21 N22 C23 C24 2.0(7) . . . . ? O21 N22 C23 C26 179.6(4) . . . . ? N22 C23 C24 N25 -97(100) . . . . ? C26 C23 C24 N25 85(100) . . . . ? N22 C23 C26 O27 179.1(5) . . . . ? C24 C23 C26 O27 -3.1(7) . . . . ? N22 C23 C26 N28 -1.1(7) . . . . ? C24 C23 C26 N28 176.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.541 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.081 #===END data_trial_4 _database_code_depnum_ccdc_archive 'CCDC 743061' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis-ammino, 2-cyano-2-oximino-acetamide silver(I) ; _chemical_name_common Ag(ACO)x2NH3 _chemical_melting_point 'decomposes on air at r.t.' _chemical_formula_moiety 'C3 H2 N3 O2, Ag N2 H6' _chemical_formula_sum 'C3 H8 Ag N5 O2' _chemical_formula_weight 254.01 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 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.8110(3) _cell_length_b 11.9184(9) _cell_length_c 8.7827(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.9910(10) _cell_angle_gamma 90.00 _cell_volume 397.95(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 107 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.595 _exptl_crystal_size_mid 0.276 _exptl_crystal_size_min 0.162 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 2.494 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7203 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 296(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 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5455 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2331 _reflns_number_gt 2197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0190P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(2) _refine_ls_number_reflns 2331 _refine_ls_number_parameters 132 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0191 _refine_ls_R_factor_gt 0.0175 _refine_ls_wR_factor_ref 0.0410 _refine_ls_wR_factor_gt 0.0399 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _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 0.48215(4) 0.733484(12) 0.699316(14) 0.05371(5) Uani 1 1 d . . . C1 C 0.9752(5) 0.76917(18) 0.2191(2) 0.0345(4) Uani 1 1 d . . . C2 C 0.9460(5) 0.79714(15) 0.3753(2) 0.0391(4) Uani 1 1 d . . . C3 C 1.0694(6) 0.65500(17) 0.1783(2) 0.0391(4) Uani 1 1 d . . . H3A H 1.105(6) 0.574(2) -0.009(2) 0.032(5) Uiso 1 1 d . . . H4A H 0.433(15) 0.518(7) 0.659(8) 0.15(2) Uiso 1 1 d . . . H5A H 0.557(12) 0.945(5) 0.787(5) 0.109(17) Uiso 1 1 d . . . H3B H 1.026(7) 0.682(2) -0.026(3) 0.046(7) Uiso 1 1 d . . . H4B H 0.726(14) 0.553(4) 0.635(6) 0.113(18) Uiso 1 1 d . . . H5B H 0.200(12) 0.915(3) 0.783(4) 0.087(12) Uiso 1 1 d . . . H4C H 0.407(18) 0.568(7) 0.501(9) 0.19(3) Uiso 1 1 d . . . H5C H 0.355(11) 0.881(4) 0.910(5) 0.096(12) Uiso 1 1 d . . . N1 N 0.9155(6) 0.84547(14) 0.1122(2) 0.0486(4) Uani 1 1 d . . . N2 N 0.9209(6) 0.8231(2) 0.4986(2) 0.0608(5) Uani 1 1 d . . . N3 N 1.0677(8) 0.63378(19) 0.0286(3) 0.0627(6) Uani 1 1 d . . . N4 N 0.5551(9) 0.5703(2) 0.6080(4) 0.0686(6) Uani 1 1 d . . . N5 N 0.3930(7) 0.88778(19) 0.8138(3) 0.0543(4) Uani 1 1 d . . . O1 O 0.8286(6) 0.94538(13) 0.1541(2) 0.0626(5) Uani 1 1 d . . . O2 O 1.1450(5) 0.58395(13) 0.27624(19) 0.0590(4) Uani 1 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 0.07068(9) 0.04190(7) 0.04844(8) 0.00138(11) 0.00346(6) -0.00356(11) C1 0.0470(10) 0.0245(8) 0.0321(8) 0.0032(6) 0.0042(7) -0.0019(6) C2 0.0467(10) 0.0326(8) 0.0380(9) 0.0054(7) 0.0042(7) -0.0007(7) C3 0.0502(10) 0.0269(9) 0.0396(10) -0.0011(7) 0.0005(8) -0.0011(8) N1 0.0772(13) 0.0326(8) 0.0367(8) 0.0055(7) 0.0086(9) 0.0059(8) N2 0.0778(13) 0.0681(13) 0.0375(9) -0.0024(9) 0.0103(8) 0.0014(11) N3 0.1101(19) 0.0350(10) 0.0434(10) -0.0034(9) 0.0082(11) 0.0104(10) N4 0.0739(16) 0.0410(10) 0.091(2) -0.0035(11) 0.0068(15) -0.0017(10) N5 0.0669(12) 0.0480(11) 0.0477(11) -0.0033(8) 0.0028(9) -0.0017(9) O1 0.1058(13) 0.0318(7) 0.0515(8) 0.0105(7) 0.0147(9) 0.0153(8) O2 0.0910(12) 0.0331(7) 0.0520(9) 0.0046(6) -0.0021(8) 0.0121(8) _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 N4 2.129(2) . ? Ag1 N5 2.134(2) . ? C1 N1 1.316(3) . ? C1 C2 1.424(3) . ? C1 C3 1.458(3) . ? C2 N2 1.136(3) . ? C3 O2 1.227(2) . ? C3 N3 1.339(3) . ? N1 O1 1.296(2) . ? N3 H3A 0.80(3) . ? N3 H3B 0.75(3) . ? N4 H4A 0.91(7) . ? N4 H4B 0.70(5) . ? N4 H4C 1.07(8) . ? N5 H5A 0.96(5) . ? N5 H5B 0.83(4) . ? N5 H5C 0.87(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 N4 Ag1 N5 173.52(11) . . ? N1 C1 C2 120.31(18) . . ? N1 C1 C3 120.18(17) . . ? C2 C1 C3 119.50(17) . . ? N2 C2 C1 177.7(2) . . ? O2 C3 N3 122.9(2) . . ? O2 C3 C1 121.44(19) . . ? N3 C3 C1 115.67(19) . . ? O1 N1 C1 117.85(17) . . ? C3 N3 H3A 126.0(16) . . ? C3 N3 H3B 118(2) . . ? H3A N3 H3B 116(3) . . ? Ag1 N4 H4A 111(4) . . ? Ag1 N4 H4B 106(4) . . ? H4A N4 H4B 98(6) . . ? Ag1 N4 H4C 107(4) . . ? H4A N4 H4C 99(5) . . ? H4B N4 H4C 135(5) . . ? Ag1 N5 H5A 111(3) . . ? Ag1 N5 H5B 110(3) . . ? H5A N5 H5B 103(4) . . ? Ag1 N5 H5C 115(3) . . ? H5A N5 H5C 117(4) . . ? H5B N5 H5C 98(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 N1 C1 C3 O2 176.0(2) . . . . ? C2 C1 C3 O2 -4.5(3) . . . . ? N1 C1 C3 N3 -4.0(3) . . . . ? C2 C1 C3 N3 175.6(2) . . . . ? C2 C1 N1 O1 -0.3(3) . . . . ? C3 C1 N1 O1 179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.274 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.064