Supplementary Material (ESI) for Metallomics # This journal is (c) The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mor300 _database_code_depnum_ccdc_archive 'CCDC 767525' #TrackingRef 'Compound_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3 (C6 H2 O2 Cl4), 2 (C12 H8 N2 O2)' _chemical_formula_sum 'C42 H22 N4 O10 Cl12' _chemical_formula_weight 1168.04 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3384(13) _cell_length_b 10.8469(15) _cell_length_c 12.0839(16) _cell_angle_alpha 99.180(3) _cell_angle_beta 104.737(3) _cell_angle_gamma 109.772(3) _cell_volume 1072.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3008 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.33 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7580 _exptl_absorpt_correction_T_max 0.9591 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.053 before and 0.020 after correction. The Ratio of minimum to maximum transmission is 0.790333. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; Hydrogen atoms attached to oxygen or nitrogen were located in the difference fourier map. Their isotropic thermal displacement parameters were fixed to be 1.5 times the equivalent one of the parent atom. O-H bond lengths were restrained to be 0.84 \%A, the N-H ones to be 0.91 \%A using DFIX. N-H bond distances are 0.90(2) \%A and 0.91(2) \%A, the O-H ones range from 80(2) \%A to 81(2) \%A. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9505 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.42 _reflns_number_total 4381 _reflns_number_gt 3579 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; 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^)+(0.0516P)^2^+0.4625P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4381 _refine_ls_number_parameters 323 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 O1 O 0.6354(2) 0.37630(18) 0.47329(15) 0.0214(4) Uani 1 1 d . . . C1 C 0.6787(3) 0.4945(3) 0.4411(2) 0.0168(5) Uani 1 1 d . . . C2 C 0.5660(3) 0.5075(3) 0.3382(2) 0.0141(5) Uani 1 1 d . . . C3 C 0.6141(3) 0.6315(3) 0.3065(2) 0.0161(5) Uani 1 1 d . . . H3 H 0.5445 0.6417 0.2393 0.019 Uiso 1 1 calc R . . C4 C 0.7580(3) 0.7366(3) 0.3700(2) 0.0164(5) Uani 1 1 d . . . N1 N 0.8112(3) 0.8567(2) 0.3465(2) 0.0221(5) Uani 1 1 d D . . H1N1 H 0.906(3) 0.923(2) 0.397(2) 0.033 Uiso 1 1 d D . . H2N1 H 0.742(3) 0.881(3) 0.297(2) 0.033 Uiso 1 1 d D . . C5 C 0.8725(3) 0.7209(3) 0.4734(2) 0.0187(6) Uani 1 1 d . . . O2 O 1.0043(2) 0.8164(2) 0.52940(16) 0.0267(4) Uani 1 1 d . . . C6 C 0.8232(3) 0.5946(3) 0.5030(2) 0.0212(6) Uani 1 1 d . . . H6 H 0.8937 0.5812 0.5675 0.025 Uiso 1 1 calc R . . N2 N 0.4250(2) 0.4082(2) 0.27880(17) 0.0140(4) Uani 1 1 d . . . C7 C 0.4855(3) 0.2745(3) 0.4137(2) 0.0182(5) Uani 1 1 d . . . C8 C 0.3811(3) 0.2906(3) 0.3170(2) 0.0150(5) Uani 1 1 d . . . C9 C 0.2294(3) 0.1856(3) 0.2595(2) 0.0190(5) Uani 1 1 d . . . H9 H 0.1564 0.1939 0.1930 0.023 Uiso 1 1 calc R . . C10 C 0.1842(3) 0.0695(3) 0.2984(2) 0.0221(6) Uani 1 1 d . . . H10 H 0.0804 -0.0015 0.2588 0.027 Uiso 1 1 calc R . . C11 C 0.2912(3) 0.0567(3) 0.3957(2) 0.0237(6) Uani 1 1 d . . . H11 H 0.2598 -0.0232 0.4221 0.028 Uiso 1 1 calc R . . C12 C 0.4410(3) 0.1582(3) 0.4533(2) 0.0232(6) Uani 1 1 d . . . H12 H 0.5136 0.1494 0.5195 0.028 Uiso 1 1 calc R . . C13 C 0.0237(3) 0.4123(2) -0.0822(2) 0.0115(5) Uani 1 1 d . . . Cl1 Cl 0.05549(7) 0.30443(6) -0.18538(5) 0.01591(15) Uani 1 1 d . . . C14 C 0.1138(3) 0.4429(2) 0.0372(2) 0.0117(5) Uani 1 1 d . . . O3 O 0.2191(2) 0.38367(18) 0.06522(14) 0.0146(4) Uani 1 1 d D . . H1O3 H 0.274(3) 0.408(3) 0.1339(16) 0.022 Uiso 1 1 d D . . C15 C 0.0876(3) 0.5317(2) 0.1181(2) 0.0113(5) Uani 1 1 d . . . Cl2 Cl 0.19651(7) 0.57175(6) 0.26728(5) 0.01393(14) Uani 1 1 d . . . C16 C 0.6276(3) 0.8654(2) 0.9730(2) 0.0141(5) Uani 1 1 d . . . O4 O 0.7413(2) 0.85430(19) 1.06244(16) 0.0204(4) Uani 1 1 d D . . H1O4 H 0.734(4) 0.777(2) 1.044(3) 0.031 Uiso 1 1 d D . . C17 C 0.4751(3) 0.7634(2) 0.9164(2) 0.0143(5) Uani 1 1 d . . . Cl3 Cl 0.42741(7) 0.61488(6) 0.95959(5) 0.01693(15) Uani 1 1 d . . . C18 C 0.3626(3) 0.7797(2) 0.8255(2) 0.0137(5) Uani 1 1 d . . . Cl4 Cl 0.17400(7) 0.65117(6) 0.75384(5) 0.01823(15) Uani 1 1 d . . . C19 C 0.3996(3) 0.8988(2) 0.7901(2) 0.0148(5) Uani 1 1 d . . . O5 O 0.2973(2) 0.92215(19) 0.70236(16) 0.0209(4) Uani 1 1 d D . . H1O5 H 0.213(3) 0.857(3) 0.666(3) 0.050(11) Uiso 1 1 d D . . C20 C 0.5526(3) 1.0019(2) 0.8480(2) 0.0147(5) Uani 1 1 d . . . Cl5 Cl 0.59977(7) 1.14961(6) 0.80328(5) 0.01923(15) Uani 1 1 d . . . C21 C 0.6651(3) 0.9854(2) 0.9381(2) 0.0154(5) Uani 1 1 d . . . Cl6 Cl 0.85541(7) 1.11200(6) 1.00590(5) 0.02071(16) 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 O1 0.0211(10) 0.0241(10) 0.0163(9) 0.0097(8) 0.0004(8) 0.0081(8) C1 0.0176(13) 0.0219(14) 0.0119(12) 0.0050(10) 0.0045(10) 0.0090(11) C2 0.0132(12) 0.0205(13) 0.0091(11) 0.0013(10) 0.0027(9) 0.0091(10) C3 0.0128(12) 0.0199(13) 0.0139(12) 0.0041(10) 0.0013(10) 0.0069(10) C4 0.0176(13) 0.0188(13) 0.0144(12) 0.0032(10) 0.0075(10) 0.0082(11) N1 0.0198(12) 0.0212(12) 0.0198(12) 0.0065(10) 0.0013(10) 0.0048(10) C5 0.0137(12) 0.0236(14) 0.0113(12) -0.0012(11) 0.0013(10) 0.0031(11) O2 0.0213(10) 0.0269(11) 0.0229(10) 0.0063(9) 0.0018(8) 0.0034(9) C6 0.0190(13) 0.0278(15) 0.0130(12) 0.0072(11) -0.0011(10) 0.0088(12) N2 0.0128(10) 0.0170(11) 0.0124(10) 0.0045(9) 0.0031(8) 0.0066(9) C7 0.0204(13) 0.0209(14) 0.0145(12) 0.0037(10) 0.0067(10) 0.0094(11) C8 0.0177(13) 0.0178(13) 0.0118(12) 0.0044(10) 0.0066(10) 0.0085(11) C9 0.0198(13) 0.0200(14) 0.0178(13) 0.0039(11) 0.0052(11) 0.0097(11) C10 0.0248(14) 0.0203(14) 0.0222(14) 0.0042(11) 0.0115(12) 0.0081(12) C11 0.0323(16) 0.0192(14) 0.0258(15) 0.0093(12) 0.0178(13) 0.0103(12) C12 0.0337(16) 0.0264(15) 0.0172(13) 0.0124(12) 0.0103(12) 0.0167(13) C13 0.0101(11) 0.0115(12) 0.0119(11) 0.0036(9) 0.0053(9) 0.0016(9) Cl1 0.0177(3) 0.0205(3) 0.0114(3) 0.0032(2) 0.0039(2) 0.0109(3) C14 0.0095(11) 0.0121(12) 0.0137(12) 0.0064(9) 0.0036(9) 0.0034(9) O3 0.0137(9) 0.0200(9) 0.0093(8) 0.0027(7) -0.0012(7) 0.0098(8) C15 0.0072(11) 0.0142(12) 0.0075(11) 0.0049(9) 0.0000(9) -0.0006(9) Cl2 0.0135(3) 0.0187(3) 0.0078(3) 0.0042(2) 0.0000(2) 0.0065(2) C16 0.0138(12) 0.0186(13) 0.0129(12) 0.0047(10) 0.0046(10) 0.0097(10) O4 0.0189(9) 0.0210(10) 0.0174(9) 0.0046(8) -0.0019(8) 0.0092(8) C17 0.0181(12) 0.0131(12) 0.0151(12) 0.0048(10) 0.0077(10) 0.0081(10) Cl3 0.0178(3) 0.0164(3) 0.0181(3) 0.0085(2) 0.0053(2) 0.0074(2) C18 0.0100(11) 0.0146(12) 0.0140(12) 0.0021(10) 0.0024(10) 0.0036(10) Cl4 0.0132(3) 0.0162(3) 0.0189(3) 0.0054(2) 0.0002(2) 0.0017(2) C19 0.0149(12) 0.0149(13) 0.0143(12) 0.0032(10) 0.0029(10) 0.0070(10) O5 0.0160(10) 0.0172(10) 0.0224(10) 0.0087(8) -0.0038(8) 0.0040(8) C20 0.0167(12) 0.0114(12) 0.0179(12) 0.0045(10) 0.0067(10) 0.0067(10) Cl5 0.0189(3) 0.0141(3) 0.0224(3) 0.0071(3) 0.0043(3) 0.0047(3) C21 0.0119(12) 0.0151(13) 0.0140(12) 0.0002(10) 0.0012(10) 0.0032(10) Cl6 0.0135(3) 0.0189(3) 0.0214(3) 0.0036(3) 0.0001(3) 0.0015(2) _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 C1 1.359(3) . ? O1 C7 1.373(3) . ? C1 C6 1.339(4) . ? C1 C2 1.471(3) . ? C2 N2 1.312(3) . ? C2 C3 1.415(3) . ? C3 C4 1.362(3) . ? C3 H3 0.9500 . ? C4 N1 1.333(3) . ? C4 C5 1.499(3) . ? N1 H1N1 0.911(18) . ? N1 H2N1 0.901(17) . ? C5 O2 1.239(3) . ? C5 C6 1.424(4) . ? C6 H6 0.9500 . ? N2 C8 1.392(3) . ? C7 C12 1.390(4) . ? C7 C8 1.395(3) . ? C8 C9 1.393(3) . ? C9 C10 1.384(4) . ? C9 H9 0.9500 . ? C10 C11 1.396(4) . ? C10 H10 0.9500 . ? C11 C12 1.368(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C15 1.386(3) 2_565 ? C13 C14 1.393(3) . ? C13 Cl1 1.723(2) . ? C14 O3 1.350(3) . ? C14 C15 1.387(3) . ? O3 H1O3 0.802(17) . ? C15 C13 1.386(3) 2_565 ? C15 Cl2 1.730(2) . ? C16 O4 1.362(3) . ? C16 C17 1.384(3) . ? C16 C21 1.392(3) . ? O4 H1O4 0.809(18) . ? C17 C18 1.394(3) . ? C17 Cl3 1.722(2) . ? C18 C19 1.385(3) . ? C18 Cl4 1.724(2) . ? C19 O5 1.354(3) . ? C19 C20 1.394(3) . ? O5 H1O5 0.811(18) . ? C20 C21 1.388(3) . ? C20 Cl5 1.725(2) . ? C21 Cl6 1.722(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 119.85(19) . . ? C6 C1 O1 119.0(2) . . ? C6 C1 C2 122.2(2) . . ? O1 C1 C2 118.8(2) . . ? N2 C2 C3 121.2(2) . . ? N2 C2 C1 121.2(2) . . ? C3 C2 C1 117.6(2) . . ? C4 C3 C2 121.5(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? N1 C4 C3 125.1(2) . . ? N1 C4 C5 114.8(2) . . ? C3 C4 C5 120.1(2) . . ? C4 N1 H1N1 118.8(19) . . ? C4 N1 H2N1 120(2) . . ? H1N1 N1 H2N1 119(3) . . ? O2 C5 C6 122.8(2) . . ? O2 C5 C4 119.6(2) . . ? C6 C5 C4 117.6(2) . . ? C1 C6 C5 120.9(2) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C2 N2 C8 118.7(2) . . ? O1 C7 C12 118.5(2) . . ? O1 C7 C8 119.8(2) . . ? C12 C7 C8 121.7(2) . . ? N2 C8 C9 120.3(2) . . ? N2 C8 C7 121.6(2) . . ? C9 C8 C7 118.1(2) . . ? C10 C9 C8 120.5(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 119.2(2) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? C15 C13 C14 121.1(2) 2_565 . ? C15 C13 Cl1 120.42(18) 2_565 . ? C14 C13 Cl1 118.50(18) . . ? O3 C14 C15 125.1(2) . . ? O3 C14 C13 117.6(2) . . ? C15 C14 C13 117.3(2) . . ? C14 O3 H1O3 115(2) . . ? C13 C15 C14 121.7(2) 2_565 . ? C13 C15 Cl2 119.67(19) 2_565 . ? C14 C15 Cl2 118.67(18) . . ? O4 C16 C17 122.9(2) . . ? O4 C16 C21 118.6(2) . . ? C17 C16 C21 118.4(2) . . ? C16 O4 H1O4 106(2) . . ? C16 C17 C18 120.8(2) . . ? C16 C17 Cl3 118.70(18) . . ? C18 C17 Cl3 120.52(19) . . ? C19 C18 C17 121.0(2) . . ? C19 C18 Cl4 118.48(18) . . ? C17 C18 Cl4 120.51(19) . . ? O5 C19 C18 124.5(2) . . ? O5 C19 C20 117.4(2) . . ? C18 C19 C20 118.1(2) . . ? C19 O5 H1O5 114(3) . . ? C21 C20 C19 121.0(2) . . ? C21 C20 Cl5 120.79(19) . . ? C19 C20 Cl5 118.22(18) . . ? C20 C21 C16 120.7(2) . . ? C20 C21 Cl6 120.34(19) . . ? C16 C21 Cl6 118.92(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C6 177.6(2) . . . . ? C7 O1 C1 C2 -3.3(3) . . . . ? C6 C1 C2 N2 -180.0(2) . . . . ? O1 C1 C2 N2 1.0(3) . . . . ? C6 C1 C2 C3 -0.9(4) . . . . ? O1 C1 C2 C3 -179.9(2) . . . . ? N2 C2 C3 C4 177.8(2) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 N1 -179.4(2) . . . . ? C2 C3 C4 C5 2.4(4) . . . . ? N1 C4 C5 O2 0.4(3) . . . . ? C3 C4 C5 O2 178.8(2) . . . . ? N1 C4 C5 C6 -179.8(2) . . . . ? C3 C4 C5 C6 -1.4(4) . . . . ? O1 C1 C6 C5 -179.1(2) . . . . ? C2 C1 C6 C5 1.9(4) . . . . ? O2 C5 C6 C1 179.1(2) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C3 C2 N2 C8 -177.3(2) . . . . ? C1 C2 N2 C8 1.8(3) . . . . ? C1 O1 C7 C12 -176.1(2) . . . . ? C1 O1 C7 C8 2.9(3) . . . . ? C2 N2 C8 C9 177.1(2) . . . . ? C2 N2 C8 C7 -2.3(3) . . . . ? O1 C7 C8 N2 0.0(4) . . . . ? C12 C7 C8 N2 178.9(2) . . . . ? O1 C7 C8 C9 -179.4(2) . . . . ? C12 C7 C8 C9 -0.5(4) . . . . ? N2 C8 C9 C10 -178.9(2) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C7 0.0(4) . . . . ? O1 C7 C12 C11 179.2(2) . . . . ? C8 C7 C12 C11 0.3(4) . . . . ? C15 C13 C14 O3 179.6(2) 2_565 . . . ? Cl1 C13 C14 O3 -1.2(3) . . . . ? C15 C13 C14 C15 -0.2(4) 2_565 . . . ? Cl1 C13 C14 C15 178.99(17) . . . . ? O3 C14 C15 C13 -179.6(2) . . . 2_565 ? C13 C14 C15 C13 0.2(4) . . . 2_565 ? O3 C14 C15 Cl2 0.0(3) . . . . ? C13 C14 C15 Cl2 179.78(16) . . . . ? O4 C16 C17 C18 179.8(2) . . . . ? C21 C16 C17 C18 0.9(4) . . . . ? O4 C16 C17 Cl3 -0.8(3) . . . . ? C21 C16 C17 Cl3 -179.66(18) . . . . ? C16 C17 C18 C19 -0.7(4) . . . . ? Cl3 C17 C18 C19 179.94(19) . . . . ? C16 C17 C18 Cl4 178.97(19) . . . . ? Cl3 C17 C18 Cl4 -0.4(3) . . . . ? C17 C18 C19 O5 179.7(2) . . . . ? Cl4 C18 C19 O5 0.1(3) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? Cl4 C18 C19 C20 -179.69(19) . . . . ? O5 C19 C20 C21 -179.3(2) . . . . ? C18 C19 C20 C21 0.5(4) . . . . ? O5 C19 C20 Cl5 -0.4(3) . . . . ? C18 C19 C20 Cl5 179.39(18) . . . . ? C19 C20 C21 C16 -0.2(4) . . . . ? Cl5 C20 C21 C16 -179.09(19) . . . . ? C19 C20 C21 Cl6 178.19(19) . . . . ? Cl5 C20 C21 Cl6 -0.7(3) . . . . ? O4 C16 C21 C20 -179.4(2) . . . . ? C17 C16 C21 C20 -0.5(4) . . . . ? O4 C16 C21 Cl6 2.2(3) . . . . ? C17 C16 C21 Cl6 -178.91(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H2N1 O5 0.901(17) 2.29(3) 2.987(3) 134(3) 2_676 O5 H1O5 O2 0.811(18) 2.07(3) 2.715(3) 136(3) 1_455 O4 H1O4 O3 0.809(18) 2.24(2) 2.974(3) 151(3) 2_666 O3 H1O3 N2 0.802(17) 1.948(19) 2.709(3) 158(3) . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.573 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.091 data_mor319 _database_code_depnum_ccdc_archive 'CCDC 767526' #TrackingRef 'mor319.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N3 O5 Ag' _chemical_formula_sum 'C12 H8 N3 O5 Ag' _chemical_formula_weight 382.08 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1653(6) _cell_length_b 10.3434(11) _cell_length_c 11.0739(12) _cell_angle_alpha 99.015(2) _cell_angle_beta 98.899(2) _cell_angle_gamma 91.963(2) _cell_volume 576.26(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6488 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 30.40 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 1.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8239 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.052 before and 0.025 after correction. The Ratio of minimum to maximum transmission is 0.868541. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; All hydrogen atoms were located in the difference fourier map and allowed to refine freely. N-H vary from 0.84(4) \%A to 0.87(4) \%A, C-H bond lengths from 90(4) \%A to 98(3) \%A. The highest residual electron density peak is located 0.77 \%A away from the silver atom. At that distance it cannot be any atom. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13379 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.48 _reflns_number_total 3469 _reflns_number_gt 3250 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; 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^)+(0.0440P)^2^+0.5833P] 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_number_reflns 3469 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.068 _refine_ls_shift/su_mean 0.004 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 O1 O 0.2460(3) 0.94756(16) 0.61592(16) 0.0158(3) Uani 1 1 d . . . C1 C 0.3726(4) 0.8357(2) 0.6226(2) 0.0141(4) Uani 1 1 d . . . C2 C 0.3249(4) 0.7559(2) 0.7164(2) 0.0139(4) Uani 1 1 d . . . C3 C 0.4596(5) 0.6398(2) 0.7214(2) 0.0164(4) Uani 1 1 d . . . H3 H 0.423(7) 0.581(3) 0.779(3) 0.021(8) Uiso 1 1 d . . . C4 C 0.6352(4) 0.6034(2) 0.6429(2) 0.0153(4) Uani 1 1 d . . . N1 N 0.7713(4) 0.4959(2) 0.6453(2) 0.0197(4) Uani 1 1 d . . . H1N1 H 0.891(8) 0.482(4) 0.602(4) 0.033(10) Uiso 1 1 d . . . H2N1 H 0.762(7) 0.456(4) 0.708(3) 0.024(8) Uiso 1 1 d . . . C5 C 0.6867(4) 0.6860(2) 0.5486(2) 0.0151(4) Uani 1 1 d . . . O2 O 0.8526(4) 0.65572(18) 0.48225(17) 0.0204(3) Uani 1 1 d . . . N2 N 0.1616(4) 0.79147(19) 0.79521(18) 0.0145(3) Uani 1 1 d . . . C6 C 0.5412(4) 0.8026(2) 0.5430(2) 0.0154(4) Uani 1 1 d . . . H6 H 0.573(6) 0.854(3) 0.485(3) 0.015(7) Uiso 1 1 d . . . C7 C 0.0769(4) 0.9842(2) 0.6975(2) 0.0146(4) Uani 1 1 d . . . C8 C 0.0319(4) 0.9059(2) 0.7851(2) 0.0143(4) Uani 1 1 d . . . C9 C -0.1530(4) 0.9447(2) 0.8619(2) 0.0160(4) Uani 1 1 d . . . H9 H -0.186(7) 0.886(3) 0.918(3) 0.020(8) Uiso 1 1 d . . . C10 C -0.2846(5) 1.0576(2) 0.8512(2) 0.0177(4) Uani 1 1 d . . . H10 H -0.406(7) 1.079(3) 0.904(3) 0.020(8) Uiso 1 1 d . . . C11 C -0.2310(5) 1.1356(2) 0.7640(2) 0.0188(4) Uani 1 1 d . . . H11 H -0.314(6) 1.211(3) 0.752(3) 0.006(6) Uiso 1 1 d . . . C12 C -0.0490(5) 1.0998(2) 0.6875(2) 0.0178(4) Uani 1 1 d . . . H12 H -0.018(7) 1.150(4) 0.632(3) 0.023(8) Uiso 1 1 d . . . Ag Ag 0.13411(3) 0.680533(18) 0.954085(17) 0.02019(7) Uani 1 1 d . . . N3 N -0.3170(4) 0.6282(2) 1.08195(19) 0.0159(4) Uani 1 1 d . . . O3 O -0.1163(4) 0.5717(2) 1.1177(2) 0.0316(5) Uani 1 1 d . . . O4 O -0.5353(4) 0.59983(19) 1.10996(19) 0.0243(4) Uani 1 1 d . . . O5 O -0.3032(4) 0.7123(2) 1.0135(2) 0.0287(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 O1 0.0176(7) 0.0143(7) 0.0169(7) 0.0054(6) 0.0034(6) 0.0032(6) C1 0.0149(9) 0.0120(9) 0.0149(9) 0.0035(7) -0.0004(7) -0.0009(7) C2 0.0143(9) 0.0131(9) 0.0140(9) 0.0044(7) -0.0001(7) -0.0008(7) C3 0.0180(10) 0.0151(10) 0.0172(10) 0.0057(8) 0.0035(8) 0.0019(8) C4 0.0150(9) 0.0126(9) 0.0181(10) 0.0046(8) 0.0003(8) 0.0000(7) N1 0.0216(10) 0.0174(9) 0.0234(10) 0.0082(8) 0.0075(8) 0.0066(7) C5 0.0134(9) 0.0153(10) 0.0161(10) 0.0037(8) 0.0005(7) -0.0010(7) O2 0.0184(8) 0.0217(8) 0.0241(8) 0.0073(7) 0.0080(7) 0.0045(6) N2 0.0137(8) 0.0141(8) 0.0160(8) 0.0044(7) 0.0014(7) 0.0009(6) C6 0.0160(10) 0.0150(10) 0.0165(10) 0.0065(8) 0.0022(8) 0.0012(8) C7 0.0148(9) 0.0138(9) 0.0146(9) 0.0026(7) 0.0007(7) 0.0007(7) C8 0.0141(9) 0.0132(9) 0.0149(9) 0.0024(7) 0.0002(7) -0.0002(7) C9 0.0158(10) 0.0160(10) 0.0158(10) 0.0024(8) 0.0016(8) -0.0002(8) C10 0.0171(10) 0.0172(10) 0.0173(10) -0.0007(8) 0.0016(8) 0.0012(8) C11 0.0187(10) 0.0159(10) 0.0206(11) 0.0018(8) 0.0007(8) 0.0034(8) C12 0.0205(11) 0.0143(10) 0.0181(10) 0.0038(8) 0.0005(8) 0.0019(8) Ag 0.01827(10) 0.02348(11) 0.02361(11) 0.01330(7) 0.00775(7) 0.00588(7) N3 0.0142(8) 0.0149(8) 0.0194(9) 0.0026(7) 0.0049(7) 0.0026(7) O3 0.0186(9) 0.0246(10) 0.0460(12) -0.0013(9) -0.0069(8) 0.0087(7) O4 0.0200(8) 0.0237(9) 0.0317(10) 0.0063(7) 0.0112(7) 0.0003(7) O5 0.0341(11) 0.0268(10) 0.0290(10) 0.0145(8) 0.0071(8) -0.0007(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 O1 C1 1.355(3) . ? O1 C7 1.371(3) . ? C1 C6 1.347(3) . ? C1 C2 1.468(3) . ? C2 N2 1.325(3) . ? C2 C3 1.413(3) . ? C3 C4 1.373(3) . ? C3 H3 0.98(3) . ? C4 N1 1.337(3) . ? C4 C5 1.497(3) . ? N1 H1N1 0.84(4) . ? N1 H2N1 0.87(4) . ? C5 O2 1.230(3) . ? C5 C6 1.447(3) . ? N2 C8 1.391(3) . ? N2 Ag 2.265(2) . ? C6 H6 0.92(3) . ? C7 C12 1.392(3) . ? C7 C8 1.398(3) . ? C8 C9 1.402(3) . ? C9 C10 1.383(3) . ? C9 H9 0.97(4) . ? C10 C11 1.405(4) . ? C10 H10 0.94(4) . ? C11 C12 1.382(3) . ? C11 H11 0.92(3) . ? C12 H12 0.90(4) . ? Ag O5 2.467(2) . ? Ag O4 2.496(2) 1_655 ? Ag O3 2.600(2) 2_567 ? Ag O3 2.737(3) . ? Ag O5 2.875(2) 1_655 ? N3 O5 1.248(3) . ? N3 O3 1.249(3) . ? N3 O4 1.252(3) . ? O3 Ag 2.600(2) 2_567 ? O4 Ag 2.496(2) 1_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 119.27(18) . . ? C6 C1 O1 118.3(2) . . ? C6 C1 C2 122.3(2) . . ? O1 C1 C2 119.3(2) . . ? N2 C2 C3 120.5(2) . . ? N2 C2 C1 121.3(2) . . ? C3 C2 C1 118.2(2) . . ? C4 C3 C2 121.3(2) . . ? C4 C3 H3 118(2) . . ? C2 C3 H3 120(2) . . ? N1 C4 C3 123.7(2) . . ? N1 C4 C5 115.9(2) . . ? C3 C4 C5 120.4(2) . . ? C4 N1 H1N1 121(3) . . ? C4 N1 H2N1 116(2) . . ? H1N1 N1 H2N1 121(4) . . ? O2 C5 C6 122.7(2) . . ? O2 C5 C4 120.0(2) . . ? C6 C5 C4 117.3(2) . . ? C2 N2 C8 118.0(2) . . ? C2 N2 Ag 120.10(15) . . ? C8 N2 Ag 121.53(15) . . ? C1 C6 C5 120.5(2) . . ? C1 C6 H6 122(2) . . ? C5 C6 H6 117(2) . . ? O1 C7 C12 117.4(2) . . ? O1 C7 C8 120.5(2) . . ? C12 C7 C8 122.1(2) . . ? N2 C8 C7 121.6(2) . . ? N2 C8 C9 120.4(2) . . ? C7 C8 C9 118.0(2) . . ? C10 C9 C8 120.6(2) . . ? C10 C9 H9 124(2) . . ? C8 C9 H9 116(2) . . ? C9 C10 C11 120.0(2) . . ? C9 C10 H10 117(2) . . ? C11 C10 H10 123(2) . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11 115.6(18) . . ? C10 C11 H11 123.9(18) . . ? C11 C12 C7 118.7(2) . . ? C11 C12 H12 119(2) . . ? C7 C12 H12 122(2) . . ? N2 Ag O5 107.40(7) . . ? N2 Ag O4 134.03(7) . 1_655 ? O5 Ag O4 115.52(6) . 1_655 ? N2 Ag O3 111.68(8) . 2_567 ? O5 Ag O3 102.00(7) . 2_567 ? O4 Ag O3 75.41(6) 1_655 2_567 ? N2 Ag O3 155.38(6) . . ? O5 Ag O3 48.66(6) . . ? O4 Ag O3 70.35(6) 1_655 . ? O3 Ag O3 73.98(8) 2_567 . ? N2 Ag O5 87.67(6) . 1_655 ? O5 Ag O5 150.36(9) . 1_655 ? O4 Ag O5 46.53(6) 1_655 1_655 ? O3 Ag O5 95.46(6) 2_567 1_655 ? O3 Ag O5 116.17(6) . 1_655 ? O5 N3 O3 119.6(2) . . ? O5 N3 O4 118.6(2) . . ? O3 N3 O4 121.7(2) . . ? N3 O3 Ag 116.07(15) . 2_567 ? N3 O3 Ag 88.77(16) . . ? Ag O3 Ag 106.02(8) 2_567 . ? N3 O4 Ag 105.25(15) . 1_455 ? N3 O5 Ag 101.80(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C6 -178.9(2) . . . . ? C7 O1 C1 C2 0.3(3) . . . . ? C6 C1 C2 N2 178.8(2) . . . . ? O1 C1 C2 N2 -0.4(3) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? O1 C1 C2 C3 -180.0(2) . . . . ? N2 C2 C3 C4 -178.1(2) . . . . ? C1 C2 C3 C4 1.5(3) . . . . ? C2 C3 C4 N1 178.7(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? N1 C4 C5 O2 -2.4(3) . . . . ? C3 C4 C5 O2 176.9(2) . . . . ? N1 C4 C5 C6 179.6(2) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C3 C2 N2 C8 -179.2(2) . . . . ? C1 C2 N2 C8 1.2(3) . . . . ? C3 C2 N2 Ag 7.6(3) . . . . ? C1 C2 N2 Ag -171.94(15) . . . . ? O1 C1 C6 C5 178.3(2) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? O2 C5 C6 C1 -176.1(2) . . . . ? C4 C5 C6 C1 1.9(3) . . . . ? C1 O1 C7 C12 180.0(2) . . . . ? C1 O1 C7 C8 -1.1(3) . . . . ? C2 N2 C8 C7 -2.0(3) . . . . ? Ag N2 C8 C7 171.04(16) . . . . ? C2 N2 C8 C9 176.7(2) . . . . ? Ag N2 C8 C9 -10.2(3) . . . . ? O1 C7 C8 N2 2.0(3) . . . . ? C12 C7 C8 N2 -179.1(2) . . . . ? O1 C7 C8 C9 -176.8(2) . . . . ? C12 C7 C8 C9 2.1(3) . . . . ? N2 C8 C9 C10 -179.2(2) . . . . ? C7 C8 C9 C10 -0.5(3) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C7 0.9(4) . . . . ? O1 C7 C12 C11 176.6(2) . . . . ? C8 C7 C12 C11 -2.3(3) . . . . ? C2 N2 Ag O5 -155.48(16) . . . . ? C8 N2 Ag O5 31.63(18) . . . . ? C2 N2 Ag O4 46.0(2) . . . 1_655 ? C8 N2 Ag O4 -126.92(16) . . . 1_655 ? C2 N2 Ag O3 -44.44(18) . . . 2_567 ? C8 N2 Ag O3 142.67(16) . . . 2_567 ? C2 N2 Ag O3 -143.34(17) . . . . ? C8 N2 Ag O3 43.8(3) . . . . ? C2 N2 Ag O5 50.51(17) . . . 1_655 ? C8 N2 Ag O5 -122.38(17) . . . 1_655 ? O5 N3 O3 Ag -117.4(2) . . . 2_567 ? O4 N3 O3 Ag 60.5(3) . . . 2_567 ? O5 N3 O3 Ag -10.1(2) . . . . ? O4 N3 O3 Ag 167.7(2) . . . . ? N2 Ag O3 N3 -9.6(2) . . . . ? O5 Ag O3 N3 5.91(13) . . . . ? O4 Ag O3 N3 163.31(15) 1_655 . . . ? O3 Ag O3 N3 -116.81(16) 2_567 . . . ? O5 Ag O3 N3 154.95(13) 1_655 . . . ? N2 Ag O3 Ag 107.22(15) . . . 2_567 ? O5 Ag O3 Ag 122.72(11) . . . 2_567 ? O4 Ag O3 Ag -79.88(7) 1_655 . . 2_567 ? O3 Ag O3 Ag 0.0 2_567 . . 2_567 ? O5 Ag O3 Ag -88.24(8) 1_655 . . 2_567 ? O5 N3 O4 Ag 18.0(2) . . . 1_455 ? O3 N3 O4 Ag -159.89(19) . . . 1_455 ? O3 N3 O5 Ag 11.5(2) . . . . ? O4 N3 O5 Ag -166.42(17) . . . . ? N2 Ag O5 N3 167.26(15) . . . . ? O4 Ag O5 N3 -29.69(17) 1_655 . . . ? O3 Ag O5 N3 49.72(16) 2_567 . . . ? O3 Ag O5 N3 -6.04(13) . . . . ? O5 Ag O5 N3 -75.1(2) 1_655 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N1 O2 0.84(4) 2.18(4) 2.931(3) 149(4) 2_766 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.038 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.140