data_global _journal_name_full Metallomics _journal_coden_Cambridge 1400 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Tacke, Matthias' _publ_contact_author_email matthias.tacke@ucd.ie _publ_section_title ; Novel Benzyl-Substituted N-Heterocyclic Carbene-Silver Acetate Complexes: Synthesis, Cytotoxicity and Antibacterial Studies ; loop_ _publ_author_name S.Patil A.Deally B.Gleeson H.Muller-Bunz F.Paradisi M.Tacke # Attachment 'tac103pub.cif' data_tac103(3c) _database_code_depnum_ccdc_archive 'CCDC 777915' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 N3, H2 O, Br' _chemical_formula_sum 'C16 H16 N3 Br O' _chemical_formula_weight 346.23 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' Br Br -0.2901 2.4595 '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' _space_group_name_Hall '-P 2yn' 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 7.0820(2) _cell_length_b 15.9788(3) _cell_length_c 13.7653(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.326(2) _cell_angle_gamma 90.00 _cell_volume 1557.68(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11184 _cell_measurement_theta_min 3.46 _cell_measurement_theta_max 24.68 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4613 _exptl_absorpt_correction_T_max 0.6202 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.081 before and 0.024 after correction. The Ratio of minimum to maximum transmission is 0.743723. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; The hydrogen atoms of the water molecule were located in the difference fourier map. Their thermal displacement parameters were fixed to 1.5 times the equivalent one of the oxygen atom. Their positional parameters were refined, and the O-H bond lengths were restrained to be 0.84 \%A using DFIX. They refined to 0.82(2) \%A. The data collection was done at room temperature without temperature control. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22628 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 24.73 _reflns_number_total 2655 _reflns_number_gt 2369 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0287P)^2^+0.9378P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2655 _refine_ls_number_parameters 197 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Br Br 0.47714(3) 0.746357(14) 0.769528(19) 0.05250(11) Uani 1 1 d . . . C1 C 0.5481(3) 0.97239(13) 0.84866(15) 0.0412(5) Uani 1 1 d . . . H1 H 0.5885 0.9171 0.8455 0.049 Uiso 1 1 calc R . . C2 C 0.3813(3) 0.99144(14) 0.89561(16) 0.0454(5) Uani 1 1 d . . . H2 H 0.3101 0.9494 0.9243 0.055 Uiso 1 1 calc R . . C3 C 0.3216(3) 1.07386(14) 0.89934(15) 0.0425(5) Uani 1 1 d . . . C7 C 0.1525(4) 1.09523(16) 0.95215(18) 0.0547(6) Uani 1 1 d . . . N1 N 0.0221(3) 1.11159(16) 0.99638(19) 0.0768(7) Uani 1 1 d . . . C4 C 0.4257(3) 1.13638(14) 0.85514(18) 0.0514(6) Uani 1 1 d . . . H4 H 0.3834 1.1915 0.8564 0.062 Uiso 1 1 calc R . . C5 C 0.5929(3) 1.11650(13) 0.80910(17) 0.0460(5) Uani 1 1 d . . . H5 H 0.6637 1.1585 0.7799 0.055 Uiso 1 1 calc R . . C6 C 0.6554(3) 1.03476(12) 0.80628(13) 0.0331(4) Uani 1 1 d . . . C8 C 0.8385(3) 1.01299(13) 0.75581(14) 0.0369(5) Uani 1 1 d . . . H8A H 0.9120 1.0635 0.7463 0.044 Uiso 1 1 calc R . . H8B H 0.9116 0.9754 0.7966 0.044 Uiso 1 1 calc R . . N2 N 0.8027(2) 0.97294(10) 0.66111(11) 0.0316(4) Uani 1 1 d . . . C9 C 0.7821(3) 0.89109(12) 0.64703(14) 0.0353(4) Uani 1 1 d . . . H9 H 0.7918 0.8507 0.6954 0.042 Uiso 1 1 calc R . . C10 C 0.7772(3) 1.01320(12) 0.57233(13) 0.0319(4) Uani 1 1 d . . . C11 C 0.7426(3) 0.95082(13) 0.50432(14) 0.0340(4) Uani 1 1 d . . . C12 C 0.7138(3) 0.96900(16) 0.40659(16) 0.0476(6) Uani 1 1 d . . . H12 H 0.6924 0.9272 0.3608 0.057 Uiso 1 1 calc R . . C13 C 0.7187(3) 1.05192(18) 0.38147(17) 0.0551(6) Uani 1 1 d . . . H13 H 0.6990 1.0668 0.3169 0.066 Uiso 1 1 calc R . . C14 C 0.7523(3) 1.11455(16) 0.44955(19) 0.0541(6) Uani 1 1 d . . . H14 H 0.7537 1.1700 0.4290 0.065 Uiso 1 1 calc R . . C15 C 0.7838(3) 1.09717(14) 0.54690(17) 0.0433(5) Uani 1 1 d . . . H15 H 0.8078 1.1390 0.5922 0.052 Uiso 1 1 calc R . . N3 N 0.7462(2) 0.87538(10) 0.55440(12) 0.0369(4) Uani 1 1 d . . . C16 C 0.7145(4) 0.79221(15) 0.51232(18) 0.0568(6) Uani 1 1 d . . . H16A H 0.8195 0.7775 0.4720 0.085 Uiso 1 1 calc R . . H16B H 0.6010 0.7929 0.4739 0.085 Uiso 1 1 calc R . . H16C H 0.7022 0.7518 0.5635 0.085 Uiso 1 1 calc R . . O O 0.0446(3) 0.81716(18) 0.80175(16) 0.0857(7) Uani 1 1 d D . . H1O H 0.155(3) 0.802(3) 0.797(3) 0.129 Uiso 1 1 d D . . H2O H 0.018(6) 0.831(3) 0.8577(17) 0.129 Uiso 1 1 d 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 Br 0.04960(16) 0.04511(16) 0.06296(18) 0.00967(10) 0.01434(12) 0.00813(10) C1 0.0512(13) 0.0356(11) 0.0369(11) -0.0029(9) 0.0061(9) 0.0019(9) C2 0.0486(13) 0.0463(12) 0.0416(12) -0.0006(10) 0.0122(10) -0.0059(10) C3 0.0382(11) 0.0528(13) 0.0366(11) -0.0065(10) 0.0055(9) 0.0026(10) C7 0.0504(14) 0.0592(15) 0.0547(14) -0.0016(12) 0.0115(12) 0.0057(12) N1 0.0655(15) 0.0800(16) 0.0852(17) 0.0046(13) 0.0349(13) 0.0178(13) C4 0.0551(14) 0.0389(12) 0.0604(15) -0.0034(11) 0.0121(11) 0.0087(10) C5 0.0468(13) 0.0381(12) 0.0534(13) -0.0025(10) 0.0112(10) -0.0023(10) C6 0.0336(10) 0.0404(11) 0.0254(9) -0.0053(8) -0.0020(8) -0.0002(8) C8 0.0345(11) 0.0445(11) 0.0317(10) -0.0069(9) -0.0025(8) 0.0003(9) N2 0.0300(8) 0.0372(9) 0.0275(8) -0.0020(7) 0.0020(6) -0.0001(7) C9 0.0358(11) 0.0362(11) 0.0339(11) 0.0012(8) 0.0070(8) 0.0021(8) C10 0.0236(9) 0.0400(11) 0.0321(10) 0.0026(8) 0.0024(7) -0.0011(8) C11 0.0255(9) 0.0457(12) 0.0308(10) -0.0012(8) 0.0043(7) -0.0035(8) C12 0.0359(12) 0.0727(16) 0.0341(11) -0.0014(11) 0.0017(9) -0.0085(11) C13 0.0417(13) 0.0867(19) 0.0368(12) 0.0193(13) -0.0017(10) -0.0077(12) C14 0.0430(13) 0.0580(15) 0.0614(15) 0.0260(13) 0.0009(11) -0.0045(11) C15 0.0369(11) 0.0437(12) 0.0493(13) 0.0058(10) 0.0005(9) -0.0050(9) N3 0.0385(9) 0.0383(9) 0.0340(9) -0.0061(7) 0.0080(7) -0.0022(7) C16 0.0696(17) 0.0448(14) 0.0563(15) -0.0184(11) 0.0102(13) -0.0051(11) O 0.0695(13) 0.1201(19) 0.0674(13) 0.0048(13) -0.0043(11) 0.0402(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(3) . ? C1 C6 1.384(3) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.385(3) . ? C3 C7 1.445(3) . ? C7 N1 1.139(3) . ? C4 C5 1.383(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C8 1.515(3) . ? C8 N2 1.473(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? N2 C9 1.330(3) . ? N2 C10 1.392(2) . ? C9 N3 1.323(3) . ? C9 H9 0.9300 . ? C10 C15 1.388(3) . ? C10 C11 1.388(3) . ? C11 N3 1.389(3) . ? C11 C12 1.390(3) . ? C12 C13 1.370(4) . ? C12 H12 0.9300 . ? C13 C14 1.391(4) . ? C13 H13 0.9300 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N3 C16 1.466(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? O H1O 0.821(19) . ? O H2O 0.821(19) . ? 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 C2 C1 C6 120.72(19) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 120.4(2) . . ? C2 C3 C7 119.8(2) . . ? C4 C3 C7 119.7(2) . . ? N1 C7 C3 177.9(3) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.51(19) . . ? C5 C6 C8 120.39(19) . . ? C1 C6 C8 120.09(18) . . ? N2 C8 C6 111.21(15) . . ? N2 C8 H8A 109.4 . . ? C6 C8 H8A 109.4 . . ? N2 C8 H8B 109.4 . . ? C6 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C9 N2 C10 108.24(16) . . ? C9 N2 C8 125.06(16) . . ? C10 N2 C8 126.66(16) . . ? N3 C9 N2 110.33(17) . . ? N3 C9 H9 124.8 . . ? N2 C9 H9 124.8 . . ? C15 C10 C11 122.01(19) . . ? C15 C10 N2 131.62(19) . . ? C11 C10 N2 106.36(17) . . ? C10 C11 N3 106.60(16) . . ? C10 C11 C12 121.8(2) . . ? N3 C11 C12 131.6(2) . . ? C13 C12 C11 116.3(2) . . ? C13 C12 H12 121.9 . . ? C11 C12 H12 121.9 . . ? C12 C13 C14 122.0(2) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C13 122.2(2) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C10 115.6(2) . . ? C14 C15 H15 122.2 . . ? C10 C15 H15 122.2 . . ? C9 N3 C11 108.46(16) . . ? C9 N3 C16 125.52(19) . . ? C11 N3 C16 126.03(18) . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? H1O O H2O 112(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 C6 C1 C2 C3 0.4(3) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C1 C2 C3 C7 -177.0(2) . . . . ? C2 C3 C4 C5 -1.7(4) . . . . ? C7 C3 C4 C5 176.5(2) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C1 1.0(3) . . . . ? C4 C5 C6 C8 180.0(2) . . . . ? C2 C1 C6 C5 -1.5(3) . . . . ? C2 C1 C6 C8 179.52(19) . . . . ? C5 C6 C8 N2 -104.4(2) . . . . ? C1 C6 C8 N2 74.6(2) . . . . ? C6 C8 N2 C9 -89.4(2) . . . . ? C6 C8 N2 C10 88.0(2) . . . . ? C10 N2 C9 N3 0.4(2) . . . . ? C8 N2 C9 N3 178.20(16) . . . . ? C9 N2 C10 C15 -179.9(2) . . . . ? C8 N2 C10 C15 2.4(3) . . . . ? C9 N2 C10 C11 -0.7(2) . . . . ? C8 N2 C10 C11 -178.42(17) . . . . ? C15 C10 C11 N3 179.96(18) . . . . ? N2 C10 C11 N3 0.7(2) . . . . ? C15 C10 C11 C12 0.4(3) . . . . ? N2 C10 C11 C12 -178.85(18) . . . . ? C10 C11 C12 C13 -0.9(3) . . . . ? N3 C11 C12 C13 179.7(2) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C10 -0.8(3) . . . . ? C11 C10 C15 C14 0.4(3) . . . . ? N2 C10 C15 C14 179.5(2) . . . . ? N2 C9 N3 C11 0.0(2) . . . . ? N2 C9 N3 C16 -179.68(19) . . . . ? C10 C11 N3 C9 -0.4(2) . . . . ? C12 C11 N3 C9 179.0(2) . . . . ? C10 C11 N3 C16 179.25(19) . . . . ? C12 C11 N3 C16 -1.3(3) . . . . ? 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 O H1O Br 0.821(19) 2.48(2) 3.298(2) 174(4) . O H2O N1 0.821(19) 2.23(2) 3.042(3) 169(4) 3_577 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.73 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.425 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.045 #===END data_tac104(3e) _database_code_depnum_ccdc_archive 'CCDC 777916' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N2, H2 O, Br' _chemical_formula_sum 'C23 H25 N2 Br O' _chemical_formula_weight 425.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 9.9811(3) _cell_length_b 10.0794(4) _cell_length_c 11.7361(3) _cell_angle_alpha 67.423(3) _cell_angle_beta 82.718(3) _cell_angle_gamma 76.645(3) _cell_volume 1059.78(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19912 _cell_measurement_theta_min 4.0798 _cell_measurement_theta_max 76.2981 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2009 _exptl_crystal_size_mid 0.1821 _exptl_crystal_size_min 0.1689 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.743 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.747 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; The hydrogen atoms of the water molecule were located in the difference fourier map. Their isotropical thermal displacement parameter was fixed to be 1.5 times the equivalent one of the oxygen atom. O-H bond lengths were restrained to be 0.82 \%A using DFIX. O-H bond lengths refined to 0.81(2) \%A. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23699 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 76.49 _reflns_number_total 4420 _reflns_number_gt 4128 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0571P)^2^+0.2625P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4420 _refine_ls_number_parameters 252 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.003 _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 Br Br 0.17850(2) 0.17978(2) 0.50528(2) 0.06351(11) Uani 1 1 d . . . C1 C 0.8435(2) 0.4418(3) 0.8476(2) 0.0680(5) Uani 1 1 d . . . H1 H 0.7833 0.5301 0.8103 0.082 Uiso 1 1 calc R . . C2 C 0.8799(3) 0.4018(4) 0.9679(3) 0.0876(8) Uani 1 1 d . . . H2 H 0.8431 0.4632 1.0111 0.105 Uiso 1 1 calc R . . C3 C 0.9689(3) 0.2741(4) 1.0236(2) 0.0833(7) Uani 1 1 d . . . H3 H 0.9922 0.2479 1.1048 0.100 Uiso 1 1 calc R . . C4 C 1.0236(3) 0.1848(3) 0.9601(3) 0.0833(8) Uani 1 1 d . . . H4 H 1.0859 0.0982 0.9974 0.100 Uiso 1 1 calc R . . C5 C 0.9870(3) 0.2223(3) 0.8398(2) 0.0672(5) Uani 1 1 d . . . H5 H 1.0241 0.1600 0.7974 0.081 Uiso 1 1 calc R . . C6 C 0.89604(18) 0.3511(2) 0.78276(17) 0.0485(4) Uani 1 1 d . . . C7 C 0.85819(17) 0.3928(2) 0.65126(17) 0.0487(4) Uani 1 1 d . . . H7A H 0.8457 0.4983 0.6096 0.058 Uiso 1 1 calc R . . H7B H 0.9330 0.3480 0.6082 0.058 Uiso 1 1 calc R . . N1 N 0.73066(14) 0.34557(15) 0.64553(13) 0.0427(3) Uani 1 1 d . . . C8 C 0.72478(18) 0.21667(19) 0.64222(16) 0.0459(4) Uani 1 1 d . . . H8 H 0.8011 0.1451 0.6384 0.055 Uiso 1 1 calc R . . C9 C 0.59647(15) 0.42166(17) 0.65283(13) 0.0382(3) Uani 1 1 d . . . C10 C 0.54468(17) 0.55925(18) 0.65938(15) 0.0422(3) Uani 1 1 d . . . H10 H 0.6031 0.6200 0.6573 0.051 Uiso 1 1 calc R . . C11 C 0.40298(18) 0.60229(18) 0.66917(15) 0.0433(3) Uani 1 1 d . . . C15 C 0.3438(2) 0.7494(2) 0.6798(2) 0.0629(5) Uani 1 1 d . . . H15A H 0.4170 0.8002 0.6714 0.094 Uiso 1 1 calc R . . H15B H 0.2969 0.7352 0.7589 0.094 Uiso 1 1 calc R . . H15C H 0.2800 0.8064 0.6157 0.094 Uiso 1 1 calc R . . C12 C 0.31409(17) 0.51030(19) 0.66961(15) 0.0437(3) Uani 1 1 d . . . C16 C 0.1599(2) 0.5592(3) 0.6806(2) 0.0622(5) Uani 1 1 d . . . H16A H 0.1152 0.4904 0.6696 0.093 Uiso 1 1 calc R . . H16B H 0.1319 0.6543 0.6183 0.093 Uiso 1 1 calc R . . H16C H 0.1344 0.5639 0.7608 0.093 Uiso 1 1 calc R . . C13 C 0.36690(17) 0.37489(18) 0.66023(15) 0.0429(3) Uani 1 1 d . . . H13 H 0.3093 0.3150 0.6589 0.052 Uiso 1 1 calc R . . C14 C 0.50961(16) 0.33214(16) 0.65284(14) 0.0385(3) Uani 1 1 d . . . N2 N 0.59433(15) 0.20461(14) 0.64513(13) 0.0430(3) Uani 1 1 d . . . C17 C 0.5485(2) 0.07372(19) 0.64866(16) 0.0491(4) Uani 1 1 d . . . H17A H 0.6176 0.0223 0.6060 0.059 Uiso 1 1 calc R . . H17B H 0.4636 0.1045 0.6053 0.059 Uiso 1 1 calc R . . C18 C 0.5253(2) -0.02928(19) 0.77890(17) 0.0473(4) Uani 1 1 d . . . C19 C 0.3946(3) -0.0309(3) 0.8322(2) 0.0683(5) Uani 1 1 d . . . H19 H 0.3193 0.0336 0.7888 0.082 Uiso 1 1 calc R . . C20 C 0.3758(4) -0.1299(4) 0.9515(3) 0.0892(9) Uani 1 1 d . . . H20 H 0.2875 -0.1313 0.9879 0.107 Uiso 1 1 calc R . . C21 C 0.4861(4) -0.2248(4) 1.0156(2) 0.0938(9) Uani 1 1 d . . . H21 H 0.4727 -0.2920 1.0946 0.113 Uiso 1 1 calc R . . C22 C 0.6169(4) -0.2209(4) 0.9633(3) 0.1056(11) Uani 1 1 d . . . H22 H 0.6922 -0.2836 1.0079 0.127 Uiso 1 1 calc R . . C23 C 0.6370(3) -0.1243(3) 0.8448(2) 0.0790(7) Uani 1 1 d . . . H23 H 0.7256 -0.1230 0.8092 0.095 Uiso 1 1 calc R . . O O 0.03649(18) 0.0510(2) 0.33245(16) 0.0705(4) Uani 1 1 d D . . H1O H -0.025(3) 0.010(4) 0.371(3) 0.106 Uiso 1 1 d D . . H2O H 0.054(4) 0.085(4) 0.380(3) 0.106 Uiso 1 1 d 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 Br 0.05702(15) 0.05349(15) 0.08087(18) -0.02315(11) -0.01241(11) -0.01017(10) C1 0.0577(12) 0.0727(14) 0.0771(14) -0.0347(11) -0.0176(10) 0.0007(10) C2 0.0809(17) 0.111(2) 0.0858(17) -0.0555(17) -0.0179(14) -0.0066(16) C3 0.0869(18) 0.099(2) 0.0654(13) -0.0209(13) -0.0242(12) -0.0260(15) C4 0.0864(17) 0.0665(14) 0.0858(17) -0.0100(13) -0.0402(14) -0.0057(13) C5 0.0659(13) 0.0565(12) 0.0759(13) -0.0208(10) -0.0190(10) -0.0032(10) C6 0.0373(8) 0.0508(9) 0.0566(9) -0.0146(8) -0.0048(7) -0.0149(7) C7 0.0376(8) 0.0509(9) 0.0535(9) -0.0124(7) -0.0017(7) -0.0127(7) N1 0.0375(7) 0.0405(7) 0.0464(7) -0.0117(5) -0.0051(5) -0.0062(5) C8 0.0442(8) 0.0408(8) 0.0475(8) -0.0134(7) -0.0060(7) -0.0013(7) C9 0.0368(7) 0.0370(7) 0.0377(7) -0.0095(6) -0.0041(6) -0.0077(6) C10 0.0432(8) 0.0371(7) 0.0464(8) -0.0131(6) -0.0043(6) -0.0110(6) C11 0.0457(8) 0.0387(8) 0.0449(8) -0.0158(6) -0.0024(6) -0.0064(6) C15 0.0614(12) 0.0513(11) 0.0820(14) -0.0352(10) 0.0025(10) -0.0068(9) C12 0.0384(8) 0.0463(8) 0.0437(8) -0.0138(6) -0.0016(6) -0.0079(6) C16 0.0400(9) 0.0669(12) 0.0800(13) -0.0302(11) 0.0019(9) -0.0081(9) C13 0.0402(8) 0.0420(8) 0.0464(8) -0.0127(6) -0.0051(6) -0.0121(6) C14 0.0415(8) 0.0338(7) 0.0383(7) -0.0101(6) -0.0057(6) -0.0074(6) N2 0.0457(7) 0.0355(7) 0.0461(7) -0.0129(5) -0.0067(5) -0.0057(5) C17 0.0608(10) 0.0391(8) 0.0506(9) -0.0174(7) -0.0086(8) -0.0113(7) C18 0.0551(10) 0.0393(8) 0.0515(9) -0.0182(7) -0.0063(7) -0.0119(7) C19 0.0615(12) 0.0600(12) 0.0819(14) -0.0247(11) 0.0062(10) -0.0167(10) C20 0.097(2) 0.0915(19) 0.0855(18) -0.0367(15) 0.0332(16) -0.0437(17) C21 0.131(3) 0.093(2) 0.0538(12) -0.0107(12) 0.0027(15) -0.047(2) C22 0.106(2) 0.094(2) 0.0790(17) 0.0165(16) -0.0267(16) -0.0217(18) C23 0.0638(13) 0.0725(15) 0.0742(14) 0.0022(12) -0.0084(11) -0.0110(11) O 0.0656(10) 0.0726(10) 0.0715(10) -0.0295(8) -0.0010(8) -0.0057(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 C1 C6 1.379(3) . ? C1 C2 1.383(4) . ? C1 H1 0.9300 . ? C2 C3 1.359(4) . ? C2 H2 0.9300 . ? C3 C4 1.360(4) . ? C3 H3 0.9300 . ? C4 C5 1.388(4) . ? C4 H4 0.9300 . ? C5 C6 1.378(3) . ? C5 H5 0.9300 . ? C6 C7 1.509(3) . ? C7 N1 1.476(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N1 C8 1.330(2) . ? N1 C9 1.391(2) . ? C8 N2 1.330(2) . ? C8 H8 0.9300 . ? C9 C14 1.388(2) . ? C9 C10 1.392(2) . ? C10 C11 1.384(2) . ? C10 H10 0.9300 . ? C11 C12 1.422(2) . ? C11 C15 1.511(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C12 C13 1.386(2) . ? C12 C16 1.509(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C13 C14 1.391(2) . ? C13 H13 0.9300 . ? C14 N2 1.394(2) . ? N2 C17 1.477(2) . ? C17 C18 1.507(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.374(3) . ? C18 C23 1.383(3) . ? C19 C20 1.393(4) . ? C19 H19 0.9300 . ? C20 C21 1.365(5) . ? C20 H20 0.9300 . ? C21 C22 1.373(5) . ? C21 H21 0.9300 . ? C22 C23 1.379(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? O H1O 0.809(18) . ? O H2O 0.814(18) . ? 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 C6 C1 C2 120.2(2) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 120.9(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 118.5(2) . . ? C5 C6 C7 120.41(19) . . ? C1 C6 C7 121.08(18) . . ? N1 C7 C6 111.76(14) . . ? N1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C8 N1 C9 108.20(14) . . ? C8 N1 C7 125.23(15) . . ? C9 N1 C7 126.38(14) . . ? N1 C8 N2 110.39(15) . . ? N1 C8 H8 124.8 . . ? N2 C8 H8 124.8 . . ? C14 C9 N1 106.71(13) . . ? C14 C9 C10 121.46(14) . . ? N1 C9 C10 131.83(14) . . ? C11 C10 C9 117.50(15) . . ? C11 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? C10 C11 C12 120.99(15) . . ? C10 C11 C15 118.71(16) . . ? C12 C11 C15 120.30(16) . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C12 C11 120.94(15) . . ? C13 C12 C16 118.91(16) . . ? C11 C12 C16 120.15(16) . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C13 C14 117.31(15) . . ? C12 C13 H13 121.3 . . ? C14 C13 H13 121.3 . . ? C9 C14 C13 121.77(15) . . ? C9 C14 N2 106.48(14) . . ? C13 C14 N2 131.74(15) . . ? C8 N2 C14 108.20(14) . . ? C8 N2 C17 125.39(15) . . ? C14 N2 C17 126.28(14) . . ? N2 C17 C18 112.13(14) . . ? N2 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N2 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C23 119.8(2) . . ? C19 C18 C17 120.74(19) . . ? C23 C18 C17 119.47(19) . . ? C18 C19 C20 119.5(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 120.1(3) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? H1O O H2O 101(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 C6 C1 C2 C3 0.8(5) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? C2 C3 C4 C5 -1.2(5) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C4 C5 C6 C7 179.0(2) . . . . ? C2 C1 C6 C5 -1.2(4) . . . . ? C2 C1 C6 C7 -179.7(2) . . . . ? C5 C6 C7 N1 94.3(2) . . . . ? C1 C6 C7 N1 -87.2(2) . . . . ? C6 C7 N1 C8 -89.7(2) . . . . ? C6 C7 N1 C9 84.7(2) . . . . ? C9 N1 C8 N2 0.89(18) . . . . ? C7 N1 C8 N2 176.12(15) . . . . ? C8 N1 C9 C14 -0.41(17) . . . . ? C7 N1 C9 C14 -175.57(14) . . . . ? C8 N1 C9 C10 179.55(17) . . . . ? C7 N1 C9 C10 4.4(3) . . . . ? C14 C9 C10 C11 1.6(2) . . . . ? N1 C9 C10 C11 -178.32(16) . . . . ? C9 C10 C11 C12 -1.4(2) . . . . ? C9 C10 C11 C15 178.43(16) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C15 C11 C12 C13 -179.85(17) . . . . ? C10 C11 C12 C16 179.89(17) . . . . ? C15 C11 C12 C16 0.0(3) . . . . ? C11 C12 C13 C14 1.2(2) . . . . ? C16 C12 C13 C14 -178.69(16) . . . . ? N1 C9 C14 C13 179.52(14) . . . . ? C10 C9 C14 C13 -0.5(2) . . . . ? N1 C9 C14 N2 -0.18(16) . . . . ? C10 C9 C14 N2 179.85(14) . . . . ? C12 C13 C14 C9 -1.0(2) . . . . ? C12 C13 C14 N2 178.63(16) . . . . ? N1 C8 N2 C14 -1.01(18) . . . . ? N1 C8 N2 C17 -176.99(15) . . . . ? C9 C14 N2 C8 0.71(17) . . . . ? C13 C14 N2 C8 -178.94(17) . . . . ? C9 C14 N2 C17 176.65(14) . . . . ? C13 C14 N2 C17 -3.0(3) . . . . ? C8 N2 C17 C18 90.9(2) . . . . ? C14 N2 C17 C18 -84.4(2) . . . . ? N2 C17 C18 C19 100.4(2) . . . . ? N2 C17 C18 C23 -80.3(2) . . . . ? C23 C18 C19 C20 -0.9(3) . . . . ? C17 C18 C19 C20 178.3(2) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C19 C20 C21 C22 1.4(5) . . . . ? C20 C21 C22 C23 -1.9(6) . . . . ? C21 C22 C23 C18 1.0(6) . . . . ? C19 C18 C23 C22 0.4(4) . . . . ? C17 C18 C23 C22 -178.9(3) . . . . ? 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 O H2O Br 0.814(18) 2.59(2) 3.3773(19) 164(4) . O H1O Br 0.809(18) 2.60(2) 3.3930(19) 166(4) 2_556 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.605 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.051 #===END data_tac107(3d) _database_code_depnum_ccdc_archive 'CCDC 777917' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 N4, Br' _chemical_formula_sum 'C25 H21 Br N4' _chemical_formula_weight 457.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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' 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 7.26900(4) _cell_length_b 12.62118(6) _cell_length_c 23.4502(1) _cell_angle_alpha 90.00 _cell_angle_beta 97.0346(5) _cell_angle_gamma 90.00 _cell_volume 2135.205(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 31367 _cell_measurement_theta_min 3.4990 _cell_measurement_theta_max 76.6743 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1924 _exptl_crystal_size_mid 0.1119 _exptl_crystal_size_min 0.0597 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 2.764 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_T_max 0.882 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _exptl_special_details ; The hydrogen atom attachec to C9 was allowed to refine freely. This one was chosen because it is involved in hydrogen bonding to Br. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43690 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0089 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 76.88 _reflns_number_total 4494 _reflns_number_gt 4217 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0306P)^2^+1.1675P] 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 4494 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_ref 0.0601 _refine_ls_wR_factor_gt 0.0593 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.004 _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 Br Br 0.253418(19) -0.144569(11) 1.017808(6) 0.02171(6) Uani 1 1 d . . . C1 C 0.1492(2) 0.12980(11) 0.78198(6) 0.0212(3) Uani 1 1 d . . . H1 H 0.2635 0.1107 0.7712 0.025 Uiso 1 1 calc R . . C2 C -0.0072(2) 0.12838(11) 0.74160(6) 0.0222(3) Uani 1 1 d . . . H2 H 0.0014 0.1076 0.7040 0.027 Uiso 1 1 calc R . . C3 C -0.1777(2) 0.15852(11) 0.75821(6) 0.0219(3) Uani 1 1 d . . . C7 C -0.3424(2) 0.15853(12) 0.71708(6) 0.0260(3) Uani 1 1 d . . . N1 N -0.4748(2) 0.15788(12) 0.68518(6) 0.0350(3) Uani 1 1 d . . . C4 C -0.1909(2) 0.18937(13) 0.81451(6) 0.0266(3) Uani 1 1 d . . . H4 H -0.3046 0.2100 0.8252 0.032 Uiso 1 1 calc R . . C5 C -0.03371(19) 0.18926(12) 0.85466(6) 0.0240(3) Uani 1 1 d . . . H5 H -0.0426 0.2092 0.8924 0.029 Uiso 1 1 calc R . . C6 C 0.13647(19) 0.15961(10) 0.83875(6) 0.0183(3) Uani 1 1 d . . . C8 C 0.31183(19) 0.15925(11) 0.88126(6) 0.0200(3) Uani 1 1 d . . . H8A H 0.3672 0.0893 0.8819 0.024 Uiso 1 1 calc R . . H8B H 0.3998 0.2090 0.8684 0.024 Uiso 1 1 calc R . . N2 N 0.27771(15) 0.18751(9) 0.93934(5) 0.0178(2) Uani 1 1 d . . . C9 C 0.25312(17) 0.11846(12) 0.98063(6) 0.0191(3) Uani 1 1 d . . . H9 H 0.257(2) 0.0471(16) 0.9755(7) 0.024(4) Uiso 1 1 d . . . C10 C 0.26756(17) 0.28979(11) 0.96112(6) 0.0173(2) Uani 1 1 d . . . C11 C 0.23364(17) 0.27872(11) 1.01798(5) 0.0178(3) Uani 1 1 d . . . C12 C 0.21497(18) 0.36648(11) 1.05258(6) 0.0192(3) Uani 1 1 d . . . H12 H 0.1916 0.3587 1.0905 0.023 Uiso 1 1 calc R . . C13 C 0.23230(17) 0.46605(11) 1.02887(6) 0.0195(3) Uani 1 1 d . . . C16 C 0.2147(2) 0.56310(12) 1.06534(6) 0.0245(3) Uani 1 1 d . . . H16A H 0.1781 0.5423 1.1017 0.037 Uiso 1 1 calc R . . H16B H 0.1230 0.6098 1.0461 0.037 Uiso 1 1 calc R . . H16C H 0.3319 0.5990 1.0715 0.037 Uiso 1 1 calc R . . C14 C 0.26740(17) 0.47755(11) 0.97059(6) 0.0194(3) Uani 1 1 d . . . C17 C 0.28535(19) 0.58642(11) 0.94543(6) 0.0234(3) Uani 1 1 d . . . H17A H 0.3144 0.5801 0.9067 0.035 Uiso 1 1 calc R . . H17B H 0.3825 0.6246 0.9681 0.035 Uiso 1 1 calc R . . H17C H 0.1705 0.6240 0.9454 0.035 Uiso 1 1 calc R . . C15 C 0.28489(17) 0.38898(11) 0.93662(6) 0.0187(3) Uani 1 1 d . . . H15 H 0.3075 0.3958 0.8986 0.022 Uiso 1 1 calc R . . N3 N 0.22638(15) 0.17010(9) 1.02849(5) 0.0181(2) Uani 1 1 d . . . C18 C 0.18874(19) 0.11959(12) 1.08187(6) 0.0211(3) Uani 1 1 d . . . H18A H 0.1549 0.0462 1.0741 0.025 Uiso 1 1 calc R . . H18B H 0.0839 0.1545 1.0957 0.025 Uiso 1 1 calc R . . C19 C 0.35289(19) 0.12359(10) 1.12832(6) 0.0191(3) Uani 1 1 d . . . C20 C 0.5287(2) 0.15276(11) 1.11675(6) 0.0229(3) Uani 1 1 d . . . H20 H 0.5476 0.1718 1.0796 0.027 Uiso 1 1 calc R . . C21 C 0.6765(2) 0.15368(12) 1.16029(6) 0.0251(3) Uani 1 1 d . . . H21 H 0.7938 0.1740 1.1524 0.030 Uiso 1 1 calc R . . C22 C 0.6484(2) 0.12409(11) 1.21581(6) 0.0229(3) Uani 1 1 d . . . C25 C 0.8027(2) 0.12696(12) 1.26088(6) 0.0258(3) Uani 1 1 d . . . N4 N 0.9268(2) 0.12946(11) 1.29609(6) 0.0315(3) Uani 1 1 d . . . C23 C 0.4732(2) 0.09366(12) 1.22779(6) 0.0257(3) Uani 1 1 d . . . H23 H 0.4548 0.0734 1.2648 0.031 Uiso 1 1 calc R . . C24 C 0.3259(2) 0.09374(11) 1.18411(6) 0.0234(3) Uani 1 1 d . . . H24 H 0.2085 0.0738 1.1920 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.02176(8) 0.01994(8) 0.02387(9) 0.00186(5) 0.00454(6) 0.00049(5) C1 0.0219(7) 0.0205(6) 0.0216(7) -0.0017(5) 0.0040(5) 0.0029(5) C2 0.0270(7) 0.0222(7) 0.0175(6) -0.0022(5) 0.0028(5) 0.0008(5) C3 0.0224(7) 0.0235(7) 0.0191(6) 0.0008(5) -0.0005(5) -0.0021(5) C7 0.0265(7) 0.0316(8) 0.0199(7) -0.0016(6) 0.0030(6) -0.0006(6) N1 0.0278(7) 0.0519(9) 0.0239(6) -0.0046(6) -0.0016(5) 0.0013(6) C4 0.0182(6) 0.0397(9) 0.0220(7) -0.0021(6) 0.0028(5) 0.0006(6) C5 0.0213(7) 0.0343(8) 0.0165(6) -0.0032(5) 0.0029(5) -0.0012(6) C6 0.0198(6) 0.0167(6) 0.0182(6) 0.0004(5) 0.0010(5) -0.0004(5) C8 0.0187(6) 0.0231(7) 0.0181(6) -0.0017(5) 0.0017(5) 0.0025(5) N2 0.0176(5) 0.0182(5) 0.0169(5) -0.0001(4) -0.0005(4) 0.0007(4) C9 0.0169(6) 0.0195(7) 0.0199(6) 0.0004(5) -0.0012(5) 0.0005(5) C10 0.0132(6) 0.0200(6) 0.0179(6) -0.0006(5) -0.0012(5) 0.0011(5) C11 0.0138(6) 0.0198(7) 0.0191(6) 0.0018(5) -0.0008(5) -0.0010(5) C12 0.0146(6) 0.0251(7) 0.0174(6) -0.0013(5) 0.0003(5) 0.0004(5) C13 0.0130(6) 0.0222(7) 0.0225(6) -0.0018(5) -0.0013(5) 0.0003(5) C16 0.0216(7) 0.0244(7) 0.0274(7) -0.0049(6) 0.0023(5) 0.0005(5) C14 0.0130(6) 0.0209(7) 0.0234(6) 0.0015(5) -0.0011(5) 0.0004(5) C17 0.0206(6) 0.0208(7) 0.0281(7) 0.0027(5) 0.0006(5) 0.0000(5) C15 0.0143(6) 0.0222(7) 0.0192(6) 0.0023(5) 0.0003(5) 0.0001(5) N3 0.0175(5) 0.0192(5) 0.0172(5) 0.0020(4) -0.0003(4) -0.0005(4) C18 0.0202(6) 0.0235(7) 0.0194(6) 0.0041(5) 0.0023(5) -0.0028(5) C19 0.0224(7) 0.0160(6) 0.0187(6) 0.0006(5) 0.0014(5) 0.0017(5) C20 0.0234(7) 0.0281(7) 0.0170(6) 0.0015(5) 0.0025(5) 0.0011(5) C21 0.0224(7) 0.0304(8) 0.0219(7) -0.0007(6) 0.0009(6) 0.0012(6) C22 0.0285(7) 0.0193(6) 0.0195(6) -0.0017(5) -0.0029(5) 0.0037(5) C25 0.0324(8) 0.0226(7) 0.0217(7) -0.0012(5) 0.0010(6) 0.0036(6) N4 0.0359(7) 0.0325(7) 0.0240(6) -0.0031(5) -0.0050(6) 0.0042(6) C23 0.0346(8) 0.0242(7) 0.0182(6) 0.0041(5) 0.0027(6) 0.0001(6) C24 0.0263(7) 0.0226(7) 0.0215(7) 0.0030(5) 0.0036(5) -0.0030(5) _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 C1 C2 1.388(2) . ? C1 C6 1.3974(19) . ? C1 H1 0.9300 . ? C2 C3 1.396(2) . ? C2 H2 0.9300 . ? C3 C4 1.391(2) . ? C3 C7 1.442(2) . ? C7 N1 1.144(2) . ? C4 C5 1.389(2) . ? C4 H4 0.9300 . ? C5 C6 1.3864(19) . ? C5 H5 0.9300 . ? C6 C8 1.5189(18) . ? C8 N2 1.4583(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? N2 C9 1.3311(18) . ? N2 C10 1.3935(17) . ? C9 N3 1.3325(18) . ? C9 H9 0.91(2) . ? C10 C15 1.3896(19) . ? C10 C11 1.3923(18) . ? C11 C12 1.3895(19) . ? C11 N3 1.3950(18) . ? C12 C13 1.386(2) . ? C12 H12 0.9300 . ? C13 C14 1.4282(19) . ? C13 C16 1.5081(19) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C14 C15 1.388(2) . ? C14 C17 1.5074(19) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C15 H15 0.9300 . ? N3 C18 1.4601(17) . ? C18 C19 1.5148(18) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.388(2) . ? C19 C24 1.3980(19) . ? C20 C21 1.389(2) . ? C20 H20 0.9300 . ? C21 C22 1.393(2) . ? C21 H21 0.9300 . ? C22 C23 1.392(2) . ? C22 C25 1.444(2) . ? C25 N4 1.146(2) . ? C23 C24 1.388(2) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? 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 C2 C1 C6 120.62(13) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C1 C2 C3 119.15(13) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 120.50(13) . . ? C4 C3 C7 119.12(13) . . ? C2 C3 C7 120.38(13) . . ? N1 C7 C3 178.80(17) . . ? C5 C4 C3 119.78(13) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.33(13) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.61(13) . . ? C5 C6 C8 121.94(12) . . ? C1 C6 C8 118.45(12) . . ? N2 C8 C6 112.77(11) . . ? N2 C8 H8A 109.0 . . ? C6 C8 H8A 109.0 . . ? N2 C8 H8B 109.0 . . ? C6 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C9 N2 C10 108.78(11) . . ? C9 N2 C8 124.94(12) . . ? C10 N2 C8 126.27(11) . . ? N2 C9 N3 109.81(13) . . ? N2 C9 H9 122.8(11) . . ? N3 C9 H9 127.4(11) . . ? C15 C10 C11 121.47(12) . . ? C15 C10 N2 132.18(12) . . ? C11 C10 N2 106.36(11) . . ? C12 C11 C10 121.38(12) . . ? C12 C11 N3 132.19(12) . . ? C10 C11 N3 106.43(12) . . ? C13 C12 C11 117.93(12) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C12 C13 C14 120.77(13) . . ? C12 C13 C16 119.39(13) . . ? C14 C13 C16 119.84(13) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C14 C13 120.48(13) . . ? C15 C14 C17 119.42(13) . . ? C13 C14 C17 120.09(13) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C15 C10 117.97(12) . . ? C14 C15 H15 121.0 . . ? C10 C15 H15 121.0 . . ? C9 N3 C11 108.62(11) . . ? C9 N3 C18 124.78(12) . . ? C11 N3 C18 126.57(12) . . ? N3 C18 C19 112.84(11) . . ? N3 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? N3 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C24 119.49(13) . . ? C20 C19 C18 122.08(12) . . ? C24 C19 C18 118.40(12) . . ? C19 C20 C21 120.42(13) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 119.74(14) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C23 C22 C21 120.35(13) . . ? C23 C22 C25 120.46(13) . . ? C21 C22 C25 119.18(14) . . ? N4 C25 C22 179.03(18) . . ? C24 C23 C22 119.52(13) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C19 120.48(14) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? 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 C6 C1 C2 C3 0.8(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C1 C2 C3 C7 179.57(13) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C7 C3 C4 C5 179.68(14) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C4 C5 C6 C8 179.52(14) . . . . ? C2 C1 C6 C5 -0.8(2) . . . . ? C2 C1 C6 C8 179.71(13) . . . . ? C5 C6 C8 N2 2.97(19) . . . . ? C1 C6 C8 N2 -177.52(12) . . . . ? C6 C8 N2 C9 96.15(15) . . . . ? C6 C8 N2 C10 -84.67(16) . . . . ? C10 N2 C9 N3 0.29(14) . . . . ? C8 N2 C9 N3 179.60(12) . . . . ? C9 N2 C10 C15 179.40(13) . . . . ? C8 N2 C10 C15 0.1(2) . . . . ? C9 N2 C10 C11 -0.53(14) . . . . ? C8 N2 C10 C11 -179.83(11) . . . . ? C15 C10 C11 C12 0.24(19) . . . . ? N2 C10 C11 C12 -179.82(11) . . . . ? C15 C10 C11 N3 -179.38(11) . . . . ? N2 C10 C11 N3 0.55(14) . . . . ? C10 C11 C12 C13 -0.39(19) . . . . ? N3 C11 C12 C13 179.13(13) . . . . ? C11 C12 C13 C14 0.28(19) . . . . ? C11 C12 C13 C16 -179.40(12) . . . . ? C12 C13 C14 C15 -0.03(19) . . . . ? C16 C13 C14 C15 179.65(12) . . . . ? C12 C13 C14 C17 179.83(12) . . . . ? C16 C13 C14 C17 -0.48(18) . . . . ? C13 C14 C15 C10 -0.12(18) . . . . ? C17 C14 C15 C10 -179.99(12) . . . . ? C11 C10 C15 C14 0.02(18) . . . . ? N2 C10 C15 C14 -179.90(13) . . . . ? N2 C9 N3 C11 0.06(14) . . . . ? N2 C9 N3 C18 177.88(12) . . . . ? C12 C11 N3 C9 -179.96(13) . . . . ? C10 C11 N3 C9 -0.39(14) . . . . ? C12 C11 N3 C18 2.3(2) . . . . ? C10 C11 N3 C18 -178.16(12) . . . . ? C9 N3 C18 C19 106.68(15) . . . . ? C11 N3 C18 C19 -75.89(17) . . . . ? N3 C18 C19 C20 -12.22(19) . . . . ? N3 C18 C19 C24 169.72(12) . . . . ? C24 C19 C20 C21 -0.8(2) . . . . ? C18 C19 C20 C21 -178.85(13) . . . . ? C19 C20 C21 C22 0.6(2) . . . . ? C20 C21 C22 C23 0.0(2) . . . . ? C20 C21 C22 C25 -179.05(13) . . . . ? C21 C22 C23 C24 -0.5(2) . . . . ? C25 C22 C23 C24 178.56(14) . . . . ? C22 C23 C24 C19 0.3(2) . . . . ? C20 C19 C24 C23 0.3(2) . . . . ? C18 C19 C24 C23 178.44(13) . . . . ? 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 C9 H9 Br 0.91(2) 2.62(2) 3.4322(15) 149.6(14) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 76.88 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.311 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.050 #===END data_tac110(4b) _database_code_depnum_ccdc_archive 'CCDC 777918' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Ag Cl2 N3 O2' _chemical_formula_sum 'C14 H12 Ag Cl2 N3 O2' _chemical_formula_weight 433.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag 0.1306 4.2820 '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' 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 4.40268(4) _cell_length_b 16.7370(2) _cell_length_c 21.1545(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.612(1) _cell_angle_gamma 90.00 _cell_volume 1558.21(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11071 _cell_measurement_theta_min 3.3649 _cell_measurement_theta_max 76.1314 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3880 _exptl_crystal_size_mid 0.0694 _exptl_crystal_size_min 0.0443 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.846 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 13.624 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.129 _exptl_absorpt_correction_T_max 0.607 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13661 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 76.32 _reflns_number_total 3244 _reflns_number_gt 3158 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0249P)^2^+8.2557P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3244 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _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 0.22282(7) 1.030983(17) 0.159652(14) 0.02106(10) Uani 1 1 d . . . C1 C 0.8141(9) 1.0279(2) 0.30170(19) 0.0187(8) Uani 1 1 d . . . H1 H 0.7364 1.0500 0.2632 0.022 Uiso 1 1 calc R . . C2 C 1.0211(9) 1.0708(2) 0.33874(19) 0.0187(8) Uani 1 1 d . . . H2 H 1.0881 1.1219 0.3253 0.022 Uiso 1 1 calc R . . C3 C 1.1309(9) 1.0387(2) 0.39598(19) 0.0185(8) Uani 1 1 d . . . C7 C 1.3420(10) 1.0844(3) 0.4351(2) 0.0214(8) Uani 1 1 d . . . N1 N 1.5076(10) 1.1211(2) 0.46590(19) 0.0292(8) Uani 1 1 d . . . C4 C 1.0378(9) 0.9631(3) 0.41542(19) 0.0202(8) Uani 1 1 d . . . H4 H 1.1146 0.9410 0.4540 0.024 Uiso 1 1 calc R . . C5 C 0.8316(9) 0.9205(2) 0.37769(19) 0.0185(8) Uani 1 1 d . . . H5 H 0.7663 0.8691 0.3908 0.022 Uiso 1 1 calc R . . C6 C 0.7195(9) 0.9524(2) 0.32087(18) 0.0167(7) Uani 1 1 d . . . C8 C 0.4868(9) 0.9061(2) 0.28139(18) 0.0184(8) Uani 1 1 d . . . H8A H 0.4427 0.8551 0.3029 0.022 Uiso 1 1 calc R . . H8B H 0.2957 0.9373 0.2784 0.022 Uiso 1 1 calc R . . N2 N 0.5895(8) 0.88918(19) 0.21725(15) 0.0164(6) Uani 1 1 d . . . C9 C 0.5101(10) 0.9333(2) 0.16524(19) 0.0197(8) Uani 1 1 d . . . C10 C 0.7832(9) 0.8277(2) 0.20155(19) 0.0171(7) Uani 1 1 d . . . Cl1 Cl 0.9174(2) 0.75866(5) 0.25419(4) 0.01893(19) Uani 1 1 d . . . C11 C 0.8257(9) 0.8331(2) 0.13863(19) 0.0183(8) Uani 1 1 d . . . Cl2 Cl 1.0372(2) 0.77433(6) 0.09185(5) 0.0242(2) Uani 1 1 d . . . N3 N 0.6590(8) 0.8981(2) 0.11737(16) 0.0196(7) Uani 1 1 d . . . C12 C 0.6335(11) 0.9246(3) 0.05094(19) 0.0255(9) Uani 1 1 d . . . H12A H 0.8222 0.9120 0.0295 0.038 Uiso 1 1 calc R . . H12B H 0.5982 0.9824 0.0495 0.038 Uiso 1 1 calc R . . H12C H 0.4633 0.8969 0.0296 0.038 Uiso 1 1 calc R . . O1 O -0.0794(7) 1.13082(18) 0.16458(14) 0.0251(7) Uani 1 1 d . . . O2 O -0.0850(8) 1.1049(2) 0.06225(15) 0.0300(7) Uani 1 1 d . . . C13 C -0.1631(9) 1.1449(3) 0.1085(2) 0.0213(8) Uani 1 1 d . . . C14 C -0.3741(11) 1.2164(3) 0.0974(2) 0.0276(9) Uani 1 1 d . . . H14A H -0.4974 1.2079 0.0587 0.041 Uiso 1 1 calc R . . H14B H -0.2524 1.2650 0.0930 0.041 Uiso 1 1 calc R . . H14C H -0.5076 1.2222 0.1334 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag 0.02295(16) 0.01760(16) 0.02245(16) 0.00140(11) -0.00294(11) 0.00072(11) C1 0.0224(19) 0.0177(19) 0.0162(18) -0.0002(15) 0.0032(15) 0.0039(16) C2 0.022(2) 0.0161(18) 0.0187(19) -0.0005(15) 0.0057(15) 0.0020(15) C3 0.0165(18) 0.0211(19) 0.0181(19) -0.0034(15) 0.0042(15) 0.0003(16) C7 0.020(2) 0.023(2) 0.021(2) 0.0011(16) 0.0030(16) 0.0041(17) N1 0.032(2) 0.028(2) 0.027(2) -0.0035(16) -0.0044(16) -0.0009(17) C4 0.0205(19) 0.024(2) 0.0162(19) 0.0014(15) 0.0030(15) 0.0031(16) C5 0.0200(19) 0.0173(18) 0.0185(19) 0.0024(15) 0.0061(15) 0.0023(15) C6 0.0147(17) 0.0199(19) 0.0159(18) -0.0024(15) 0.0048(14) 0.0016(15) C8 0.0177(19) 0.0221(19) 0.0155(18) -0.0010(15) 0.0037(15) -0.0001(16) N2 0.0170(16) 0.0164(15) 0.0157(15) -0.0008(12) 0.0008(12) -0.0015(13) C9 0.025(2) 0.0154(18) 0.0182(19) -0.0010(15) -0.0023(16) -0.0003(16) C10 0.0183(18) 0.0153(18) 0.0176(18) 0.0012(14) -0.0006(15) -0.0012(15) Cl1 0.0233(4) 0.0170(4) 0.0165(4) 0.0016(3) -0.0002(3) 0.0015(3) C11 0.0199(19) 0.0177(18) 0.0172(19) -0.0007(15) 0.0002(15) -0.0041(15) Cl2 0.0307(5) 0.0227(5) 0.0195(5) -0.0045(4) 0.0072(4) -0.0029(4) N3 0.0235(18) 0.0186(16) 0.0166(16) 0.0025(13) -0.0040(13) -0.0050(14) C12 0.038(3) 0.025(2) 0.0129(19) 0.0011(16) -0.0026(17) -0.0041(19) O1 0.0331(17) 0.0203(14) 0.0217(15) -0.0026(12) -0.0015(13) 0.0057(13) O2 0.0371(18) 0.0319(17) 0.0213(15) -0.0048(13) 0.0038(13) 0.0053(14) C13 0.0168(19) 0.020(2) 0.027(2) -0.0070(16) 0.0027(16) -0.0043(16) C14 0.029(2) 0.025(2) 0.030(2) -0.0008(18) -0.0024(18) 0.0054(18) _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 C9 2.069(4) . ? Ag O1 2.140(3) . ? C1 C2 1.385(6) . ? C1 C6 1.396(6) . ? C1 H1 0.9500 . ? C2 C3 1.399(6) . ? C2 H2 0.9500 . ? C3 C4 1.395(6) . ? C3 C7 1.447(6) . ? C7 N1 1.142(6) . ? C4 C5 1.389(6) . ? C4 H4 0.9500 . ? C5 C6 1.393(6) . ? C5 H5 0.9500 . ? C6 C8 1.516(5) . ? C8 N2 1.470(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N2 C9 1.362(5) . ? N2 C10 1.383(5) . ? C9 N3 1.356(5) . ? C10 C11 1.352(6) . ? C10 Cl1 1.700(4) . ? C11 N3 1.382(5) . ? C11 Cl2 1.693(4) . ? N3 C12 1.474(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O1 C13 1.255(5) . ? O2 C13 1.241(5) . ? C13 C14 1.530(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C9 Ag O1 173.86(14) . . ? C2 C1 C6 120.1(4) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C1 C2 C3 119.8(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 120.4(4) . . ? C4 C3 C7 120.0(4) . . ? C2 C3 C7 119.6(4) . . ? N1 C7 C3 179.4(5) . . ? C5 C4 C3 119.3(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.6(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.8(4) . . ? C5 C6 C8 119.9(4) . . ? C1 C6 C8 120.3(4) . . ? N2 C8 C6 112.7(3) . . ? N2 C8 H8A 109.0 . . ? C6 C8 H8A 109.0 . . ? N2 C8 H8B 109.0 . . ? C6 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C9 N2 C10 110.8(3) . . ? C9 N2 C8 124.2(3) . . ? C10 N2 C8 125.0(3) . . ? N3 C9 N2 104.5(3) . . ? N3 C9 Ag 127.4(3) . . ? N2 C9 Ag 128.1(3) . . ? C11 C10 N2 106.9(3) . . ? C11 C10 Cl1 129.4(3) . . ? N2 C10 Cl1 123.6(3) . . ? C10 C11 N3 106.6(4) . . ? C10 C11 Cl2 129.1(3) . . ? N3 C11 Cl2 124.3(3) . . ? C9 N3 C11 111.2(3) . . ? C9 N3 C12 123.8(4) . . ? C11 N3 C12 124.9(4) . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 O1 Ag 105.5(3) . . ? O2 C13 O1 124.3(4) . . ? O2 C13 C14 118.8(4) . . ? O1 C13 C14 116.9(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 C6 C1 C2 C3 -1.1(6) . . . . ? C1 C2 C3 C4 1.2(6) . . . . ? C1 C2 C3 C7 -178.7(4) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C7 C3 C4 C5 179.1(4) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C4 C5 C6 C1 -0.3(6) . . . . ? C4 C5 C6 C8 -178.0(4) . . . . ? C2 C1 C6 C5 0.6(6) . . . . ? C2 C1 C6 C8 178.4(4) . . . . ? C5 C6 C8 N2 -121.7(4) . . . . ? C1 C6 C8 N2 60.6(5) . . . . ? C6 C8 N2 C9 -97.9(4) . . . . ? C6 C8 N2 C10 80.7(5) . . . . ? C10 N2 C9 N3 -0.2(4) . . . . ? C8 N2 C9 N3 178.6(3) . . . . ? C10 N2 C9 Ag 179.0(3) . . . . ? C8 N2 C9 Ag -2.1(6) . . . . ? C9 N2 C10 C11 -0.2(5) . . . . ? C8 N2 C10 C11 -179.0(4) . . . . ? C9 N2 C10 Cl1 -177.6(3) . . . . ? C8 N2 C10 Cl1 3.6(6) . . . . ? N2 C10 C11 N3 0.5(4) . . . . ? Cl1 C10 C11 N3 177.7(3) . . . . ? N2 C10 C11 Cl2 -179.5(3) . . . . ? Cl1 C10 C11 Cl2 -2.3(6) . . . . ? N2 C9 N3 C11 0.6(4) . . . . ? Ag C9 N3 C11 -178.7(3) . . . . ? N2 C9 N3 C12 178.1(4) . . . . ? Ag C9 N3 C12 -1.2(6) . . . . ? C10 C11 N3 C9 -0.7(5) . . . . ? Cl2 C11 N3 C9 179.4(3) . . . . ? C10 C11 N3 C12 -178.2(4) . . . . ? Cl2 C11 N3 C12 1.8(6) . . . . ? Ag O1 C13 O2 2.1(5) . . . . ? Ag O1 C13 C14 -177.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 76.32 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.310 _refine_diff_density_min -0.888 _refine_diff_density_rms 0.117 #===END data_tac112(4d) _database_code_depnum_ccdc_archive 'CCDC 777919' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H23 Ag N4 O2' _chemical_formula_sum 'C27 H23 Ag N4 O2' _chemical_formula_weight 543.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag 0.1306 4.2820 '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 2/n' _symmetry_space_group_name_Hall '-P 2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 15.3823(1) _cell_length_b 7.83949(7) _cell_length_c 19.8044(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.7996(7) _cell_angle_gamma 90.00 _cell_volume 2371.40(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22106 _cell_measurement_theta_min 3.4445 _cell_measurement_theta_max 76.5275 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1983 _exptl_crystal_size_mid 0.0912 _exptl_crystal_size_min 0.0700 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 7.075 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.521 _exptl_absorpt_correction_T_max 0.744 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31155 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 70.99 _reflns_number_total 4589 _reflns_number_gt 4225 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0723P)^2^+1.3852P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4589 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.004 _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 -0.023957(12) 0.30405(2) 0.507553(9) 0.02339(10) Uani 1 1 d . . . C1 C 0.1314(2) 0.1893(4) 0.26706(15) 0.0278(6) Uani 1 1 d . . . H1 H 0.1386 0.2974 0.2468 0.033 Uiso 1 1 calc R . . C2 C 0.1371(2) 0.0422(4) 0.22897(14) 0.0306(6) Uani 1 1 d . . . H2 H 0.1478 0.0495 0.1828 0.037 Uiso 1 1 calc R . . C3 C 0.12709(19) -0.1163(4) 0.25876(14) 0.0257(6) Uani 1 1 d . . . C7 C 0.1372(2) -0.2723(4) 0.22219(15) 0.0320(7) Uani 1 1 d . . . N1 N 0.1462(2) -0.3986(4) 0.19515(13) 0.0402(7) Uani 1 1 d . . . C4 C 0.1098(2) -0.1261(4) 0.32604(15) 0.0341(7) Uani 1 1 d . . . H4 H 0.1021 -0.2341 0.3463 0.041 Uiso 1 1 calc R . . C5 C 0.1037(2) 0.0213(4) 0.36342(14) 0.0324(6) Uani 1 1 d . . . H5 H 0.0915 0.0141 0.4093 0.039 Uiso 1 1 calc R . . C6 C 0.11528(19) 0.1807(3) 0.33434(14) 0.0220(6) Uani 1 1 d . . . C8 C 0.11130(19) 0.3409(4) 0.37704(13) 0.0223(5) Uani 1 1 d . . . H8A H 0.1415 0.4353 0.3561 0.027 Uiso 1 1 calc R . . H8B H 0.0494 0.3744 0.3781 0.027 Uiso 1 1 calc R . . N2 N 0.15250(16) 0.3131(3) 0.44628(12) 0.0187(5) Uani 1 1 d . . . C9 C 0.10778(18) 0.2890(3) 0.50032(15) 0.0188(5) Uani 1 1 d . . . C10 C 0.24197(19) 0.2976(3) 0.46424(14) 0.0198(6) Uani 1 1 d . . . C11 C 0.31235(19) 0.3124(3) 0.42696(14) 0.0202(6) Uani 1 1 d . . . H11 H 0.3039 0.3391 0.3799 0.024 Uiso 1 1 calc R . . C12 C 0.39616(19) 0.2868(3) 0.46097(14) 0.0223(6) Uani 1 1 d . . . C13 C 0.40760(17) 0.2457(4) 0.53131(13) 0.0215(5) Uani 1 1 d . . . C14 C 0.33627(18) 0.2351(4) 0.56821(13) 0.0218(5) Uani 1 1 d . . . H14 H 0.3438 0.2095 0.6154 0.026 Uiso 1 1 calc R . . C15 C 0.25349(18) 0.2632(4) 0.53344(13) 0.0202(5) Uani 1 1 d . . . N3 N 0.16985(15) 0.2585(3) 0.55366(11) 0.0209(4) Uani 1 1 d . . . C16 C 0.4750(2) 0.3010(4) 0.42239(15) 0.0262(6) Uani 1 1 d . . . H16A H 0.4565 0.3426 0.3763 0.039 Uiso 1 1 calc R . . H16B H 0.5024 0.1887 0.4200 0.039 Uiso 1 1 calc R . . H16C H 0.5173 0.3810 0.4459 0.039 Uiso 1 1 calc R . . C17 C 0.4980(2) 0.2117(4) 0.56732(15) 0.0276(6) Uani 1 1 d . . . H17A H 0.4933 0.1696 0.6134 0.041 Uiso 1 1 calc R . . H17B H 0.5322 0.3175 0.5700 0.041 Uiso 1 1 calc R . . H17C H 0.5273 0.1258 0.5420 0.041 Uiso 1 1 calc R . . C18 C 0.1502(2) 0.2224(4) 0.62238(14) 0.0236(6) Uani 1 1 d . . . H18A H 0.1981 0.1526 0.6461 0.028 Uiso 1 1 calc R . . H18B H 0.0956 0.1547 0.6199 0.028 Uiso 1 1 calc R . . C19 C 0.13948(17) 0.3827(4) 0.66359(13) 0.0210(5) Uani 1 1 d . . . C20 C 0.15902(19) 0.5423(4) 0.63944(14) 0.0271(6) Uani 1 1 d . . . H20 H 0.1800 0.5520 0.5964 0.033 Uiso 1 1 calc R . . C21 C 0.1484(2) 0.6877(4) 0.67707(16) 0.0284(6) Uani 1 1 d . . . H21 H 0.1624 0.7965 0.6601 0.034 Uiso 1 1 calc R . . C22 C 0.1171(2) 0.6738(4) 0.73997(15) 0.0276(6) Uani 1 1 d . . . C25 C 0.1070(2) 0.8286(4) 0.77817(16) 0.0339(7) Uani 1 1 d . . . N4 N 0.0995(2) 0.9537(4) 0.80590(15) 0.0455(7) Uani 1 1 d . . . C23 C 0.0966(2) 0.5146(4) 0.76463(15) 0.0357(7) Uani 1 1 d . . . H23 H 0.0751 0.5052 0.8075 0.043 Uiso 1 1 calc R . . C24 C 0.1076(2) 0.3698(4) 0.72661(14) 0.0307(6) Uani 1 1 d . . . H24 H 0.0934 0.2611 0.7434 0.037 Uiso 1 1 calc R . . O1 O -0.15346(14) 0.3201(3) 0.53261(11) 0.0258(5) Uani 1 1 d . . . O2 O -0.16890(15) 0.1102(3) 0.45689(11) 0.0330(5) Uani 1 1 d . . . C26 C -0.1986(2) 0.2067(4) 0.49813(16) 0.0269(6) Uani 1 1 d . . . C27 C -0.2930(2) 0.1941(5) 0.5112(2) 0.0438(9) Uani 1 1 d . . . H27A H -0.3236 0.1113 0.4798 0.066 Uiso 1 1 calc R . . H27B H -0.3211 0.3060 0.5041 0.066 Uiso 1 1 calc R . . H27C H -0.2958 0.1569 0.5581 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag 0.02286(15) 0.02106(16) 0.02750(14) 0.00047(6) 0.00813(9) 0.00061(6) C1 0.0416(17) 0.0191(16) 0.0223(14) 0.0028(10) 0.0015(12) -0.0012(11) C2 0.0452(16) 0.0250(16) 0.0215(13) -0.0006(11) 0.0039(11) 0.0009(13) C3 0.0324(14) 0.0217(15) 0.0222(12) -0.0028(10) -0.0009(10) 0.0008(11) C7 0.0465(18) 0.0247(16) 0.0230(13) 0.0009(12) -0.0028(12) 0.0004(14) N1 0.0652(19) 0.0254(14) 0.0288(13) -0.0041(11) 0.0007(12) 0.0045(13) C4 0.057(2) 0.0178(16) 0.0274(14) 0.0015(11) 0.0052(13) -0.0047(14) C5 0.0519(18) 0.0239(16) 0.0228(13) 0.0014(11) 0.0099(12) -0.0023(14) C6 0.0243(14) 0.0192(14) 0.0217(13) -0.0012(9) 0.0000(10) -0.0003(10) C8 0.0274(13) 0.0188(13) 0.0201(12) -0.0002(10) 0.0008(10) 0.0016(11) N2 0.0214(11) 0.0149(12) 0.0198(11) -0.0003(7) 0.0028(9) 0.0013(8) C9 0.0147(13) 0.0165(13) 0.0264(13) -0.0003(9) 0.0079(10) -0.0007(9) C10 0.0241(14) 0.0154(14) 0.0200(13) -0.0018(8) 0.0031(10) 0.0011(9) C11 0.0258(14) 0.0166(14) 0.0186(12) -0.0002(8) 0.0047(10) 0.0008(9) C12 0.0267(14) 0.0187(14) 0.0226(13) 0.0004(9) 0.0069(11) -0.0017(10) C13 0.0247(13) 0.0172(13) 0.0225(12) -0.0009(10) 0.0017(10) -0.0034(11) C14 0.0283(14) 0.0175(13) 0.0201(12) 0.0001(10) 0.0043(10) -0.0012(11) C15 0.0275(13) 0.0139(13) 0.0203(12) -0.0016(10) 0.0074(10) 0.0005(11) N3 0.0235(11) 0.0204(12) 0.0201(10) 0.0005(9) 0.0075(8) 0.0005(10) C16 0.0262(15) 0.0275(17) 0.0259(14) 0.0030(10) 0.0073(11) 0.0001(10) C17 0.0273(15) 0.0275(16) 0.0282(14) 0.0046(11) 0.0040(11) -0.0007(11) C18 0.0306(15) 0.0196(14) 0.0222(13) 0.0028(10) 0.0096(11) 0.0014(11) C19 0.0218(12) 0.0211(14) 0.0206(12) -0.0010(10) 0.0051(9) 0.0003(10) C20 0.0346(14) 0.0235(15) 0.0254(13) -0.0006(11) 0.0125(11) -0.0016(11) C21 0.0362(16) 0.0226(16) 0.0272(14) 0.0001(10) 0.0077(12) -0.0021(11) C22 0.0322(16) 0.0277(16) 0.0228(13) -0.0057(11) 0.0028(11) -0.0012(12) C25 0.0462(19) 0.0299(18) 0.0264(14) -0.0034(12) 0.0082(13) -0.0038(14) N4 0.069(2) 0.0320(16) 0.0381(14) -0.0130(12) 0.0158(13) -0.0057(14) C23 0.0550(19) 0.0312(18) 0.0235(13) -0.0009(12) 0.0151(12) 0.0002(15) C24 0.0458(17) 0.0230(16) 0.0250(13) 0.0021(11) 0.0112(12) -0.0026(13) O1 0.0200(10) 0.0247(11) 0.0340(11) -0.0021(8) 0.0090(8) 0.0006(7) O2 0.0407(12) 0.0258(12) 0.0355(11) -0.0035(8) 0.0162(9) -0.0027(9) C26 0.0306(16) 0.0209(15) 0.0304(15) 0.0040(10) 0.0086(12) 0.0001(11) C27 0.0323(18) 0.035(2) 0.066(3) -0.0126(15) 0.0132(17) -0.0057(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag C9 2.052(3) . ? Ag O1 2.113(2) . ? C1 C6 1.385(4) . ? C1 C2 1.387(4) . ? C1 H1 0.9500 . ? C2 C3 1.392(4) . ? C2 H2 0.9500 . ? C3 C4 1.391(4) . ? C3 C7 1.440(4) . ? C7 N1 1.142(4) . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.396(4) . ? C5 H5 0.9500 . ? C6 C8 1.520(4) . ? C8 N2 1.457(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N2 C9 1.352(4) . ? N2 C10 1.385(4) . ? C9 N3 1.359(4) . ? C10 C11 1.386(4) . ? C10 C15 1.387(4) . ? C11 C12 1.397(4) . ? C11 H11 0.9500 . ? C12 C13 1.420(4) . ? C12 C16 1.513(4) . ? C13 C14 1.391(4) . ? C13 C17 1.510(4) . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 N3 1.393(4) . ? N3 C18 1.456(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.518(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.385(4) . ? C19 C24 1.398(4) . ? C20 C21 1.382(4) . ? C20 H20 0.9500 . ? C21 C22 1.392(4) . ? C21 H21 0.9500 . ? C22 C23 1.390(5) . ? C22 C25 1.448(4) . ? C25 N4 1.137(4) . ? C23 C24 1.383(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? O1 C26 1.276(4) . ? O2 C26 1.239(4) . ? C26 C27 1.508(5) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 C9 Ag O1 170.49(10) . . ? C6 C1 C2 120.8(3) . . ? C6 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.6(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 119.9(3) . . ? C4 C3 C7 118.6(3) . . ? C2 C3 C7 121.4(3) . . ? N1 C7 C3 177.8(3) . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.1(2) . . ? C1 C6 C8 121.2(2) . . ? C5 C6 C8 119.6(2) . . ? N2 C8 C6 111.0(2) . . ? N2 C8 H8A 109.4 . . ? C6 C8 H8A 109.4 . . ? N2 C8 H8B 109.4 . . ? C6 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C9 N2 C10 111.6(2) . . ? C9 N2 C8 124.1(2) . . ? C10 N2 C8 124.2(2) . . ? N2 C9 N3 105.3(2) . . ? N2 C9 Ag 130.3(2) . . ? N3 C9 Ag 124.4(2) . . ? N2 C10 C11 132.1(3) . . ? N2 C10 C15 106.1(2) . . ? C11 C10 C15 121.7(3) . . ? C10 C11 C12 117.8(3) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C11 C12 C13 120.4(2) . . ? C11 C12 C16 119.7(3) . . ? C13 C12 C16 119.9(3) . . ? C14 C13 C12 121.0(2) . . ? C14 C13 C17 118.8(2) . . ? C12 C13 C17 120.2(2) . . ? C13 C14 C15 117.6(2) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C10 C15 C14 121.5(2) . . ? C10 C15 N3 106.0(2) . . ? C14 C15 N3 132.5(2) . . ? C9 N3 C15 111.1(2) . . ? C9 N3 C18 123.8(2) . . ? C15 N3 C18 125.1(2) . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 C19 112.9(2) . . ? N3 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? N3 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C24 119.2(3) . . ? C20 C19 C18 121.3(2) . . ? C24 C19 C18 119.5(3) . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 119.6(3) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C23 C22 C21 120.1(3) . . ? C23 C22 C25 121.7(3) . . ? C21 C22 C25 118.2(3) . . ? N4 C25 C22 177.2(4) . . ? C24 C23 C22 119.9(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C19 120.3(3) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C26 O1 Ag 107.55(19) . . ? O2 C26 O1 123.9(3) . . ? O2 C26 C27 120.7(3) . . ? O1 C26 C27 115.4(3) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 C6 C1 C2 C3 -0.4(5) . . . . ? C1 C2 C3 C4 1.2(5) . . . . ? C1 C2 C3 C7 -176.6(3) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? C7 C3 C4 C5 177.0(3) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C2 C1 C6 C5 -0.8(5) . . . . ? C2 C1 C6 C8 178.4(3) . . . . ? C4 C5 C6 C1 1.2(5) . . . . ? C4 C5 C6 C8 -178.0(3) . . . . ? C1 C6 C8 N2 -140.9(3) . . . . ? C5 C6 C8 N2 38.3(4) . . . . ? C6 C8 N2 C9 -103.6(3) . . . . ? C6 C8 N2 C10 72.3(3) . . . . ? C10 N2 C9 N3 0.3(3) . . . . ? C8 N2 C9 N3 176.6(2) . . . . ? C10 N2 C9 Ag 177.39(18) . . . . ? C8 N2 C9 Ag -6.3(4) . . . . ? C9 N2 C10 C11 -179.6(3) . . . . ? C8 N2 C10 C11 4.1(4) . . . . ? C9 N2 C10 C15 -0.5(3) . . . . ? C8 N2 C10 C15 -176.8(2) . . . . ? N2 C10 C11 C12 -179.2(3) . . . . ? C15 C10 C11 C12 1.8(4) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C10 C11 C12 C16 179.8(2) . . . . ? C11 C12 C13 C14 -1.9(4) . . . . ? C16 C12 C13 C14 178.7(3) . . . . ? C11 C12 C13 C17 177.7(3) . . . . ? C16 C12 C13 C17 -1.6(4) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? C17 C13 C14 C15 -178.6(3) . . . . ? N2 C10 C15 C14 178.1(3) . . . . ? C11 C10 C15 C14 -2.6(4) . . . . ? N2 C10 C15 N3 0.4(3) . . . . ? C11 C10 C15 N3 179.7(2) . . . . ? C13 C14 C15 C10 1.1(4) . . . . ? C13 C14 C15 N3 178.1(3) . . . . ? N2 C9 N3 C15 0.0(3) . . . . ? Ag C9 N3 C15 -177.32(19) . . . . ? N2 C9 N3 C18 -178.9(2) . . . . ? Ag C9 N3 C18 3.8(4) . . . . ? C10 C15 N3 C9 -0.3(3) . . . . ? C14 C15 N3 C9 -177.6(3) . . . . ? C10 C15 N3 C18 178.6(3) . . . . ? C14 C15 N3 C18 1.3(5) . . . . ? C9 N3 C18 C19 -85.8(3) . . . . ? C15 N3 C18 C19 95.4(3) . . . . ? N3 C18 C19 C20 -8.4(4) . . . . ? N3 C18 C19 C24 170.4(3) . . . . ? C24 C19 C20 C21 0.8(4) . . . . ? C18 C19 C20 C21 179.5(3) . . . . ? C19 C20 C21 C22 -0.4(5) . . . . ? C20 C21 C22 C23 -0.1(5) . . . . ? C20 C21 C22 C25 179.9(3) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C25 C22 C23 C24 -179.7(3) . . . . ? C22 C23 C24 C19 0.2(5) . . . . ? C20 C19 C24 C23 -0.7(5) . . . . ? C18 C19 C24 C23 -179.4(3) . . . . ? Ag O1 C26 O2 -1.4(4) . . . . ? Ag O1 C26 C27 177.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.171 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.100 #===END data_tac116(4f) _database_code_depnum_ccdc_archive 'CCDC 777920' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C62 H54 Ag2 N4 O4 ' _chemical_formula_sum 'C62 H54 Ag2 N4 O4 ' _chemical_formula_weight 1134.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.9368(7) _cell_length_b 9.5997(2) _cell_length_c 25.2845(7) _cell_angle_alpha 90.00 _cell_angle_beta 119.297(4) _cell_angle_gamma 90.00 _cell_volume 5066.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15516 _cell_measurement_theta_min 3.6907 _cell_measurement_theta_max 76.6904 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1491 _exptl_crystal_size_mid 0.0309 _exptl_crystal_size_min 0.0169 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 6.625 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.608 _exptl_absorpt_correction_T_max 0.905 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24441 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 76.89 _reflns_number_total 5254 _reflns_number_gt 4726 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0293P)^2^+4.4420P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5254 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0564 _refine_ls_wR_factor_gt 0.0551 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag Ag 0.463396(6) 0.097235(13) 0.015242(5) 0.01829(5) Uani 1 1 d . . . C1 C 0.70493(9) 0.2643(2) 0.22045(8) 0.0223(4) Uani 1 1 d . . . H1 H 0.7379 0.2047 0.2231 0.027 Uiso 1 1 calc R . . C2 C 0.71608(9) 0.3484(2) 0.26950(9) 0.0262(4) Uani 1 1 d . . . H2 H 0.7563 0.3449 0.3057 0.031 Uiso 1 1 calc R . . C3 C 0.66867(10) 0.4371(2) 0.26561(9) 0.0250(4) Uani 1 1 d . . . H3 H 0.6765 0.4964 0.2986 0.030 Uiso 1 1 calc R . . C4 C 0.60950(10) 0.4389(2) 0.21308(9) 0.0242(4) Uani 1 1 d . . . H4 H 0.5767 0.4990 0.2104 0.029 Uiso 1 1 calc R . . C5 C 0.59799(9) 0.3538(2) 0.16460(8) 0.0212(4) Uani 1 1 d . . . H5 H 0.5572 0.3550 0.1291 0.025 Uiso 1 1 calc R . . C6 C 0.64585(9) 0.26656(18) 0.16755(8) 0.0172(3) Uani 1 1 d . . . C7 C 0.63310(8) 0.17070(18) 0.11513(8) 0.0178(3) Uani 1 1 d . . . H7A H 0.6744 0.1353 0.1205 0.021 Uiso 1 1 calc R . . H7B H 0.6077 0.0898 0.1156 0.021 Uiso 1 1 calc R . . N1 N 0.52400(7) 0.30180(16) -0.03158(6) 0.0157(3) Uani 1 1 d . . . C8 C 0.53637(8) 0.21780(18) 0.01581(8) 0.0159(3) Uani 1 1 d . . . C9 C 0.62531(8) 0.34012(18) 0.03487(8) 0.0165(3) Uani 1 1 d . . . C11 C 0.69378(8) 0.37820(19) 0.06644(8) 0.0174(3) Uani 1 1 d . . . C12 C 0.71514(9) 0.50644(19) 0.09595(8) 0.0209(4) Uani 1 1 d . . . H12 H 0.6857 0.5694 0.0982 0.025 Uiso 1 1 calc R . . C13 C 0.77967(10) 0.5412(2) 0.12195(9) 0.0260(4) Uani 1 1 d . . . H13 H 0.7942 0.6283 0.1419 0.031 Uiso 1 1 calc R . . C14 C 0.82271(9) 0.4508(2) 0.11915(9) 0.0289(4) Uani 1 1 d . . . H14 H 0.8666 0.4758 0.1368 0.035 Uiso 1 1 calc R . . C15 C 0.80194(11) 0.3232(3) 0.09052(11) 0.0361(5) Uani 1 1 d . . . H15 H 0.8317 0.2600 0.0890 0.043 Uiso 1 1 calc R . . C16 C 0.73749(10) 0.2879(2) 0.06401(10) 0.0290(4) Uani 1 1 d . . . H16 H 0.7233 0.2007 0.0440 0.035 Uiso 1 1 calc R . . C10 C 0.57795(8) 0.37819(18) -0.02123(8) 0.0160(3) Uani 1 1 d . . . C17 C 0.58007(8) 0.47296(19) -0.06617(8) 0.0169(3) Uani 1 1 d . . . C18 C 0.60024(8) 0.61073(19) -0.05083(8) 0.0182(3) Uani 1 1 d . . . H18 H 0.6119 0.6443 -0.0114 0.022 Uiso 1 1 calc R . . C19 C 0.60346(9) 0.6993(2) -0.09284(9) 0.0222(4) Uani 1 1 d . . . H19 H 0.6172 0.7929 -0.0821 0.027 Uiso 1 1 calc R . . C20 C 0.58664(9) 0.6510(2) -0.15046(9) 0.0240(4) Uani 1 1 d . . . H20 H 0.5889 0.7114 -0.1791 0.029 Uiso 1 1 calc R . . C21 C 0.56653(9) 0.5145(2) -0.16616(8) 0.0243(4) Uani 1 1 d . . . H21 H 0.5549 0.4815 -0.2056 0.029 Uiso 1 1 calc R . . C22 C 0.56334(9) 0.4261(2) -0.12447(8) 0.0210(4) Uani 1 1 d . . . H22 H 0.5496 0.3326 -0.1356 0.025 Uiso 1 1 calc R . . N2 N 0.59847(7) 0.24094(15) 0.05630(6) 0.0157(3) Uani 1 1 d . . . C23 C 0.46122(8) 0.30821(19) -0.08600(8) 0.0176(3) Uani 1 1 d . . . H23A H 0.4569 0.3993 -0.1060 0.021 Uiso 1 1 calc R . . H23B H 0.4278 0.3032 -0.0738 0.021 Uiso 1 1 calc R . . C24 C 0.44929(8) 0.19354(18) -0.13151(8) 0.0170(3) Uani 1 1 d . . . C25 C 0.49591(9) 0.09840(19) -0.12550(8) 0.0194(3) Uani 1 1 d . . . H25 H 0.5380 0.1041 -0.0918 0.023 Uiso 1 1 calc R . . C26 C 0.48060(10) -0.0053(2) -0.16909(9) 0.0236(4) Uani 1 1 d . . . H26 H 0.5124 -0.0705 -0.1648 0.028 Uiso 1 1 calc R . . C27 C 0.41956(10) -0.0145(2) -0.21848(9) 0.0260(4) Uani 1 1 d . . . H27 H 0.4096 -0.0853 -0.2480 0.031 Uiso 1 1 calc R . . C28 C 0.37289(10) 0.0807(2) -0.22463(9) 0.0260(4) Uani 1 1 d . . . H28 H 0.3310 0.0753 -0.2585 0.031 Uiso 1 1 calc R . . C29 C 0.38776(9) 0.1838(2) -0.18110(8) 0.0214(4) Uani 1 1 d . . . H29 H 0.3557 0.2482 -0.1852 0.026 Uiso 1 1 calc R . . O1 O 0.37297(6) 0.02848(14) 0.00549(6) 0.0219(3) Uani 1 1 d . . . O2 O 0.33797(7) 0.16291(15) -0.07663(6) 0.0254(3) Uani 1 1 d . . . C30 C 0.32874(9) 0.09429(19) -0.03998(8) 0.0198(3) Uani 1 1 d . . . C31 C 0.26218(10) 0.0893(2) -0.04707(10) 0.0281(4) Uani 1 1 d . . . H31A H 0.2475 0.1843 -0.0464 0.042 Uiso 1 1 calc R . . H31B H 0.2632 0.0355 -0.0137 0.042 Uiso 1 1 calc R . . H31C H 0.2327 0.0449 -0.0858 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag 0.01342(7) 0.02061(8) 0.01936(7) 0.00104(5) 0.00687(5) -0.00093(4) C1 0.0142(9) 0.0291(10) 0.0190(8) -0.0010(7) 0.0046(7) 0.0014(7) C2 0.0158(9) 0.0384(11) 0.0172(8) -0.0038(8) 0.0024(7) -0.0014(8) C3 0.0262(10) 0.0308(10) 0.0179(8) -0.0034(7) 0.0108(8) -0.0019(8) C4 0.0231(9) 0.0296(10) 0.0196(8) 0.0026(7) 0.0102(8) 0.0068(8) C5 0.0162(9) 0.0281(9) 0.0138(8) 0.0035(7) 0.0031(7) 0.0029(7) C6 0.0165(8) 0.0186(8) 0.0142(7) 0.0016(6) 0.0058(7) -0.0012(6) C7 0.0158(8) 0.0180(8) 0.0143(7) 0.0018(6) 0.0032(7) 0.0017(6) N1 0.0123(7) 0.0183(7) 0.0137(6) -0.0008(5) 0.0042(6) -0.0017(5) C8 0.0143(8) 0.0166(8) 0.0149(7) -0.0018(6) 0.0057(6) -0.0013(6) C9 0.0156(8) 0.0175(8) 0.0148(7) -0.0014(6) 0.0062(7) -0.0010(6) C11 0.0147(8) 0.0202(8) 0.0140(7) 0.0015(6) 0.0044(7) -0.0007(6) C12 0.0176(9) 0.0189(8) 0.0200(8) 0.0004(7) 0.0044(7) 0.0001(7) C13 0.0223(10) 0.0267(10) 0.0202(9) 0.0001(7) 0.0035(8) -0.0070(7) C14 0.0140(9) 0.0446(12) 0.0221(9) 0.0019(8) 0.0042(8) -0.0073(8) C15 0.0201(10) 0.0455(13) 0.0419(12) -0.0089(10) 0.0146(10) 0.0028(9) C16 0.0198(10) 0.0303(10) 0.0332(10) -0.0106(8) 0.0100(9) -0.0021(8) C10 0.0141(8) 0.0162(8) 0.0153(7) -0.0015(6) 0.0053(7) -0.0007(6) C17 0.0106(8) 0.0223(9) 0.0150(7) 0.0014(6) 0.0042(6) 0.0000(6) C18 0.0158(8) 0.0195(8) 0.0181(8) 0.0005(6) 0.0073(7) 0.0018(6) C19 0.0200(9) 0.0207(9) 0.0259(9) 0.0047(7) 0.0113(8) 0.0020(7) C20 0.0195(9) 0.0315(10) 0.0205(9) 0.0093(7) 0.0094(8) 0.0025(7) C21 0.0200(9) 0.0359(11) 0.0153(8) -0.0005(7) 0.0074(7) -0.0026(8) C22 0.0172(9) 0.0257(9) 0.0180(8) -0.0011(7) 0.0069(7) -0.0028(7) N2 0.0131(7) 0.0170(7) 0.0135(6) -0.0001(5) 0.0038(6) -0.0002(5) C23 0.0125(8) 0.0209(8) 0.0139(7) 0.0012(6) 0.0021(7) 0.0002(6) C24 0.0153(8) 0.0186(8) 0.0144(7) 0.0025(6) 0.0051(7) -0.0014(6) C25 0.0157(8) 0.0225(9) 0.0157(8) 0.0030(6) 0.0043(7) 0.0001(7) C26 0.0243(10) 0.0223(9) 0.0237(9) 0.0022(7) 0.0112(8) 0.0028(7) C27 0.0300(11) 0.0256(10) 0.0186(8) -0.0051(7) 0.0090(8) -0.0023(8) C28 0.0202(9) 0.0337(10) 0.0169(8) -0.0039(7) 0.0035(7) -0.0033(8) C29 0.0150(9) 0.0259(9) 0.0184(8) -0.0005(7) 0.0043(7) 0.0007(7) O1 0.0127(6) 0.0249(7) 0.0251(6) 0.0044(5) 0.0068(5) -0.0003(5) O2 0.0228(7) 0.0289(7) 0.0226(6) 0.0033(5) 0.0095(6) 0.0005(5) C30 0.0171(9) 0.0184(8) 0.0206(8) -0.0039(6) 0.0067(7) -0.0007(6) C31 0.0173(9) 0.0343(11) 0.0309(10) 0.0028(8) 0.0105(8) 0.0027(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 Ag C8 2.0896(17) . ? Ag O1 2.1585(12) . ? Ag Ag 2.9107(3) 5_655 ? C1 C6 1.392(3) . ? C1 C2 1.392(3) . ? C1 H1 0.9500 . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C7 1.517(2) . ? C7 N2 1.465(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N1 C8 1.351(2) . ? N1 C10 1.394(2) . ? N1 C23 1.460(2) . ? C8 N2 1.348(2) . ? C9 C10 1.363(2) . ? C9 N2 1.398(2) . ? C9 C11 1.475(2) . ? C11 C16 1.383(3) . ? C11 C12 1.400(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C14 1.375(3) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C10 C17 1.476(2) . ? C17 C18 1.396(3) . ? C17 C22 1.399(2) . ? C18 C19 1.392(3) . ? C18 H18 0.9500 . ? C19 C20 1.388(3) . ? C19 H19 0.9500 . ? C20 C21 1.385(3) . ? C20 H20 0.9500 . ? C21 C22 1.384(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.515(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.392(3) . ? C24 C29 1.394(3) . ? C25 C26 1.395(3) . ? C25 H25 0.9500 . ? C26 C27 1.384(3) . ? C26 H26 0.9500 . ? C27 C28 1.392(3) . ? C27 H27 0.9500 . ? C28 C29 1.391(3) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? O1 C30 1.285(2) . ? O2 C30 1.242(2) . ? C30 C31 1.514(3) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? 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 C8 Ag O1 163.40(6) . . ? C8 Ag Ag 75.37(5) . 5_655 ? O1 Ag Ag 118.27(4) . 5_655 ? C6 C1 C2 120.56(18) . . ? C6 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 120.06(18) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.52(18) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.51(18) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.40(17) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 118.92(16) . . ? C5 C6 C7 120.67(16) . . ? C1 C6 C7 120.36(16) . . ? N2 C7 C6 112.32(14) . . ? N2 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? N2 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C8 N1 C10 111.51(14) . . ? C8 N1 C23 122.59(15) . . ? C10 N1 C23 125.90(14) . . ? N2 C8 N1 104.88(14) . . ? N2 C8 Ag 134.73(13) . . ? N1 C8 Ag 120.31(12) . . ? C10 C9 N2 106.27(15) . . ? C10 C9 C11 129.41(16) . . ? N2 C9 C11 123.96(15) . . ? C16 C11 C12 119.21(17) . . ? C16 C11 C9 119.00(17) . . ? C12 C11 C9 121.70(16) . . ? C13 C12 C11 119.61(18) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.72(19) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.91(19) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.8(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.7(2) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C9 C10 N1 106.06(15) . . ? C9 C10 C17 129.96(16) . . ? N1 C10 C17 123.89(15) . . ? C18 C17 C22 118.62(16) . . ? C18 C17 C10 120.50(16) . . ? C22 C17 C10 120.87(16) . . ? C19 C18 C17 120.49(17) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 120.06(18) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.92(17) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.16(17) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.75(18) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? C8 N2 C9 111.28(14) . . ? C8 N2 C7 124.12(15) . . ? C9 N2 C7 124.60(15) . . ? N1 C23 C24 114.18(15) . . ? N1 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? N1 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C25 C24 C29 119.49(17) . . ? C25 C24 C23 123.43(16) . . ? C29 C24 C23 117.07(16) . . ? C24 C25 C26 119.72(17) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C27 C26 C25 120.74(18) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 119.64(18) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C29 C28 C27 119.89(18) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C24 120.52(18) . . ? C28 C29 H29 119.7 . . ? C24 C29 H29 119.7 . . ? C30 O1 Ag 107.04(11) . . ? O2 C30 O1 124.00(17) . . ? O2 C30 C31 119.30(17) . . ? O1 C30 C31 116.68(17) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? 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 C6 C1 C2 C3 -1.1(3) . . . . ? C1 C2 C3 C4 1.6(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C1 1.3(3) . . . . ? C4 C5 C6 C7 178.64(17) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C2 C1 C6 C7 -177.68(17) . . . . ? C5 C6 C7 N2 44.5(2) . . . . ? C1 C6 C7 N2 -138.17(17) . . . . ? C10 N1 C8 N2 -0.11(19) . . . . ? C23 N1 C8 N2 179.81(15) . . . . ? C10 N1 C8 Ag 177.09(11) . . . . ? C23 N1 C8 Ag -3.0(2) . . . . ? O1 Ag C8 N2 131.3(2) . . . . ? Ag Ag C8 N2 -81.77(17) 5_655 . . . ? O1 Ag C8 N1 -44.9(3) . . . . ? Ag Ag C8 N1 102.05(13) 5_655 . . . ? C10 C9 C11 C16 -96.5(2) . . . . ? N2 C9 C11 C16 75.7(2) . . . . ? C10 C9 C11 C12 80.0(2) . . . . ? N2 C9 C11 C12 -107.8(2) . . . . ? C16 C11 C12 C13 0.4(3) . . . . ? C9 C11 C12 C13 -176.12(17) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C12 C11 C16 C15 0.1(3) . . . . ? C9 C11 C16 C15 176.7(2) . . . . ? C14 C15 C16 C11 -0.7(4) . . . . ? N2 C9 C10 N1 0.52(18) . . . . ? C11 C9 C10 N1 173.74(17) . . . . ? N2 C9 C10 C17 -176.04(17) . . . . ? C11 C9 C10 C17 -2.8(3) . . . . ? C8 N1 C10 C9 -0.3(2) . . . . ? C23 N1 C10 C9 179.82(16) . . . . ? C8 N1 C10 C17 176.55(16) . . . . ? C23 N1 C10 C17 -3.4(3) . . . . ? C9 C10 C17 C18 -57.0(3) . . . . ? N1 C10 C17 C18 126.97(18) . . . . ? C9 C10 C17 C22 121.5(2) . . . . ? N1 C10 C17 C22 -54.5(2) . . . . ? C22 C17 C18 C19 0.1(3) . . . . ? C10 C17 C18 C19 178.71(16) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 -0.2(3) . . . . ? C20 C21 C22 C17 0.2(3) . . . . ? C18 C17 C22 C21 -0.2(3) . . . . ? C10 C17 C22 C21 -178.77(17) . . . . ? N1 C8 N2 C9 0.44(19) . . . . ? Ag C8 N2 C9 -176.15(13) . . . . ? N1 C8 N2 C7 -179.51(15) . . . . ? Ag C8 N2 C7 3.9(3) . . . . ? C10 C9 N2 C8 -0.62(19) . . . . ? C11 C9 N2 C8 -174.31(16) . . . . ? C10 C9 N2 C7 179.33(15) . . . . ? C11 C9 N2 C7 5.6(3) . . . . ? C6 C7 N2 C8 -107.18(19) . . . . ? C6 C7 N2 C9 72.9(2) . . . . ? C8 N1 C23 C24 -82.3(2) . . . . ? C10 N1 C23 C24 97.6(2) . . . . ? N1 C23 C24 C25 -6.3(2) . . . . ? N1 C23 C24 C29 172.73(15) . . . . ? C29 C24 C25 C26 0.0(3) . . . . ? C23 C24 C25 C26 179.05(16) . . . . ? C24 C25 C26 C27 0.3(3) . . . . ? C25 C26 C27 C28 -0.2(3) . . . . ? C26 C27 C28 C29 -0.2(3) . . . . ? C27 C28 C29 C24 0.6(3) . . . . ? C25 C24 C29 C28 -0.5(3) . . . . ? C23 C24 C29 C28 -179.53(17) . . . . ? C8 Ag O1 C30 33.8(3) . . . . ? Ag Ag O1 C30 -109.34(11) 5_655 . . . ? Ag O1 C30 O2 12.0(2) . . . . ? Ag O1 C30 C31 -166.21(13) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.348 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.061 #===END data_tac117(4e) _database_code_depnum_ccdc_archive 'CCDC 777921' #TrackingRef 'tac103pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 Ag N2 O2' _chemical_formula_sum 'C25 H25 Ag N2 O2' _chemical_formula_weight 493.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag 0.1306 4.2820 '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' 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 11.7885(3) _cell_length_b 47.3901(8) _cell_length_c 7.8129(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.281(2) _cell_angle_gamma 90.00 _cell_volume 4307.60(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 23580 _cell_measurement_theta_min 3.7278 _cell_measurement_theta_max 76.7564 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2133 _exptl_crystal_size_mid 0.1538 _exptl_crystal_size_min 0.1219 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 7.692 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.367 _exptl_absorpt_correction_T_max 0.563 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; The highest residual electron density is 0.76 \%A away from Ag1 and thus certainly not an atom. We consider it likely to be part of the abortion ripples which are common around atoms as heavy as silver. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47192 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -59 _diffrn_reflns_limit_k_max 59 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 76.95 _reflns_number_total 9032 _reflns_number_gt 8691 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0001P)^2^+29.4623P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9032 _refine_ls_number_parameters 547 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.005 _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 0.98567(3) 0.849426(6) 0.81147(4) 0.02196(8) Uani 1 1 d . . . C1 C 0.8502(3) 0.89964(9) 0.3329(5) 0.0187(8) Uani 1 1 d . . . H1 H 0.9161 0.8887 0.3768 0.022 Uiso 1 1 calc R . . C2 C 0.8277(4) 0.90673(10) 0.1588(6) 0.0218(9) Uani 1 1 d . . . H2 H 0.8788 0.9008 0.0835 0.026 Uiso 1 1 calc R . . C3 C 0.7313(4) 0.92241(9) 0.0935(5) 0.0200(9) Uani 1 1 d . . . H3 H 0.7172 0.9274 -0.0259 0.024 Uiso 1 1 calc R . . C4 C 0.6558(4) 0.93080(9) 0.2013(6) 0.0207(9) Uani 1 1 d . . . H4 H 0.5886 0.9411 0.1561 0.025 Uiso 1 1 calc R . . C5 C 0.6788(4) 0.92401(9) 0.3772(5) 0.0190(8) Uani 1 1 d . . . H5 H 0.6276 0.9300 0.4522 0.023 Uiso 1 1 calc R . . C6 C 0.7758(3) 0.90854(8) 0.4430(5) 0.0158(8) Uani 1 1 d . . . C7 C 0.7991(3) 0.90097(9) 0.6338(5) 0.0172(8) Uani 1 1 d . . . H7A H 0.7396 0.9098 0.6925 0.021 Uiso 1 1 calc R . . H7B H 0.7929 0.8803 0.6461 0.021 Uiso 1 1 calc R . . N1 N 0.9128(3) 0.91012(7) 0.7200(4) 0.0138(6) Uani 1 1 d . . . C8 C 0.9998(4) 0.89285(8) 0.7906(5) 0.0149(8) Uani 1 1 d . . . C9 C 0.9467(3) 0.93833(8) 0.7358(5) 0.0151(8) Uani 1 1 d . . . C10 C 0.8887(4) 0.96327(9) 0.6854(5) 0.0205(9) Uani 1 1 d . . . H10 H 0.8108 0.9632 0.6303 0.025 Uiso 1 1 calc R . . C11 C 0.9495(4) 0.98838(9) 0.7189(6) 0.0236(9) Uani 1 1 d . . . C15 C 0.8900(5) 1.01589(10) 0.6657(6) 0.0334(12) Uani 1 1 d . . . H15A H 0.8112 1.0121 0.6083 0.050 Uiso 1 1 calc R . . H15B H 0.9319 1.0259 0.5854 0.050 Uiso 1 1 calc R . . H15C H 0.8881 1.0276 0.7687 0.050 Uiso 1 1 calc R . . C12 C 1.0658(4) 0.98833(9) 0.7999(5) 0.0222(9) Uani 1 1 d . . . C16 C 1.1302(5) 1.01572(10) 0.8334(6) 0.0326(11) Uani 1 1 d . . . H16A H 1.2081 1.0119 0.8941 0.049 Uiso 1 1 calc R . . H16B H 1.0901 1.0280 0.9051 0.049 Uiso 1 1 calc R . . H16C H 1.1344 1.0251 0.7228 0.049 Uiso 1 1 calc R . . C13 C 1.1222(4) 0.96313(9) 0.8511(5) 0.0196(8) Uani 1 1 d . . . H13 H 1.2001 0.9630 0.9062 0.023 Uiso 1 1 calc R . . C14 C 1.0603(4) 0.93821(8) 0.8187(5) 0.0153(8) Uani 1 1 d . . . N2 N 1.0892(3) 0.90998(7) 0.8514(4) 0.0130(6) Uani 1 1 d . . . C17 C 1.2010(3) 0.90094(9) 0.9432(5) 0.0168(8) Uani 1 1 d . . . H17A H 1.2619 0.9087 0.8831 0.020 Uiso 1 1 calc R . . H17B H 1.2055 0.8801 0.9386 0.020 Uiso 1 1 calc R . . C18 C 1.2233(3) 0.91030(8) 1.1309(5) 0.0143(8) Uani 1 1 d . . . C19 C 1.1451(3) 0.90400(8) 1.2412(5) 0.0165(8) Uani 1 1 d . . . H19 H 1.0769 0.8939 1.1984 0.020 Uiso 1 1 calc R . . C20 C 1.1664(4) 0.91246(9) 1.4136(5) 0.0179(8) Uani 1 1 d . . . H20 H 1.1121 0.9083 1.4877 0.021 Uiso 1 1 calc R . . C21 C 1.2665(4) 0.92696(9) 1.4784(5) 0.0190(8) Uani 1 1 d . . . H21 H 1.2812 0.9327 1.5964 0.023 Uiso 1 1 calc R . . C22 C 1.3449(4) 0.93294(9) 1.3685(6) 0.0218(9) Uani 1 1 d . . . H22 H 1.4139 0.9427 1.4121 0.026 Uiso 1 1 calc R . . C23 C 1.3236(4) 0.92481(9) 1.1961(6) 0.0211(9) Uani 1 1 d . . . H23 H 1.3776 0.9292 1.1220 0.025 Uiso 1 1 calc R . . O1 O 0.9305(3) 0.80675(7) 0.8567(4) 0.0280(7) Uani 1 1 d . . . O2 O 1.0693(3) 0.79902(8) 0.7053(5) 0.0380(9) Uani 1 1 d . . . C24 C 0.9927(4) 0.79033(9) 0.7826(5) 0.0205(9) Uani 1 1 d . . . C25 C 0.9729(7) 0.75925(11) 0.7951(8) 0.0494(16) Uani 1 1 d . . . H25A H 0.8917 0.7558 0.8014 0.074 Uiso 1 1 calc R . . H25B H 1.0207 0.7518 0.8996 0.074 Uiso 1 1 calc R . . H25C H 0.9932 0.7498 0.6926 0.074 Uiso 1 1 calc R . . Ag2 Ag 0.50549(3) 0.900413(6) 0.76662(4) 0.01814(8) Uani 1 1 d . . . C26 C 0.3426(3) 0.84754(9) 0.3361(5) 0.0176(8) Uani 1 1 d . . . H26 H 0.4124 0.8569 0.3809 0.021 Uiso 1 1 calc R . . C27 C 0.3218(4) 0.83924(9) 0.1635(5) 0.0196(8) Uani 1 1 d . . . H27 H 0.3779 0.8426 0.0913 0.024 Uiso 1 1 calc R . . C28 C 0.2194(4) 0.82609(9) 0.0965(5) 0.0192(8) Uani 1 1 d . . . H28 H 0.2052 0.8205 -0.0217 0.023 Uiso 1 1 calc R . . C29 C 0.1375(4) 0.82115(9) 0.2022(6) 0.0214(9) Uani 1 1 d . . . H29 H 0.0665 0.8124 0.1561 0.026 Uiso 1 1 calc R . . C30 C 0.1598(4) 0.82906(9) 0.3769(5) 0.0186(8) Uani 1 1 d . . . H30 H 0.1046 0.8253 0.4502 0.022 Uiso 1 1 calc R . . C31 C 0.2623(3) 0.84230(8) 0.4431(5) 0.0137(7) Uani 1 1 d . . . C32 C 0.2847(3) 0.85125(9) 0.6315(5) 0.0160(8) Uani 1 1 d . . . H32A H 0.2840 0.8721 0.6375 0.019 Uiso 1 1 calc R . . H32B H 0.2218 0.8441 0.6896 0.019 Uiso 1 1 calc R . . N3 N 0.3940(3) 0.84096(7) 0.7248(4) 0.0132(6) Uani 1 1 d . . . C33 C 0.4868(3) 0.85711(8) 0.7872(5) 0.0135(7) Uani 1 1 d . . . C34 C 0.4189(3) 0.81234(8) 0.7536(5) 0.0147(8) Uani 1 1 d . . . C35 C 0.3527(4) 0.78814(9) 0.7150(5) 0.0184(8) Uani 1 1 d . . . H35 H 0.2746 0.7893 0.6608 0.022 Uiso 1 1 calc R . . C36 C 0.4048(4) 0.76245(9) 0.7587(6) 0.0220(9) Uani 1 1 d . . . C40 C 0.3371(5) 0.73564(9) 0.7175(6) 0.0284(10) Uani 1 1 d . . . H40A H 0.2593 0.7403 0.6597 0.043 Uiso 1 1 calc R . . H40B H 0.3330 0.7254 0.8251 0.043 Uiso 1 1 calc R . . H40C H 0.3752 0.7238 0.6407 0.043 Uiso 1 1 calc R . . C37 C 0.5212(4) 0.76091(9) 0.8416(6) 0.0224(9) Uani 1 1 d . . . C41 C 0.5774(5) 0.73254(9) 0.8853(6) 0.0298(11) Uani 1 1 d . . . H41A H 0.6558 0.7354 0.9470 0.045 Uiso 1 1 calc R . . H41B H 0.5800 0.7220 0.7781 0.045 Uiso 1 1 calc R . . H41C H 0.5328 0.7219 0.9590 0.045 Uiso 1 1 calc R . . C38 C 0.5854(4) 0.78531(9) 0.8825(5) 0.0191(8) Uani 1 1 d . . . H38 H 0.6629 0.7844 0.9393 0.023 Uiso 1 1 calc R . . C39 C 0.5322(4) 0.81107(8) 0.8374(5) 0.0147(8) Uani 1 1 d . . . N4 N 0.5707(3) 0.83881(7) 0.8568(4) 0.0140(6) Uani 1 1 d . . . C42 C 0.6863(3) 0.84669(9) 0.9415(5) 0.0170(8) Uani 1 1 d . . . H42A H 0.6962 0.8673 0.9304 0.020 Uiso 1 1 calc R . . H42B H 0.7436 0.8372 0.8814 0.020 Uiso 1 1 calc R . . C43 C 0.7091(3) 0.83873(8) 1.1321(5) 0.0146(8) Uani 1 1 d . . . C44 C 0.6381(3) 0.84817(9) 1.2450(5) 0.0181(8) Uani 1 1 d . . . H44 H 0.5736 0.8597 1.2032 0.022 Uiso 1 1 calc R . . C45 C 0.6608(4) 0.84085(9) 1.4189(5) 0.0195(8) Uani 1 1 d . . . H45 H 0.6109 0.8471 1.4952 0.023 Uiso 1 1 calc R . . C46 C 0.7557(4) 0.82442(9) 1.4825(5) 0.0205(9) Uani 1 1 d . . . H46 H 0.7710 0.8194 1.6017 0.025 Uiso 1 1 calc R . . C47 C 0.8283(4) 0.81537(9) 1.3700(6) 0.0213(9) Uani 1 1 d . . . H47 H 0.8945 0.8045 1.4128 0.026 Uiso 1 1 calc R . . C48 C 0.8042(4) 0.82224(9) 1.1952(6) 0.0204(9) Uani 1 1 d . . . H48 H 0.8529 0.8156 1.1182 0.024 Uiso 1 1 calc R . . O3 O 0.5601(3) 0.94238(6) 0.7216(4) 0.0224(6) Uani 1 1 d . . . O4 O 0.4169(3) 0.95329(8) 0.8636(4) 0.0311(8) Uani 1 1 d . . . C49 C 0.4967(4) 0.96013(9) 0.7862(5) 0.0199(9) Uani 1 1 d . . . C50 C 0.5237(5) 0.99095(10) 0.7636(7) 0.0349(12) Uani 1 1 d . . . H50A H 0.4521 1.0013 0.7252 0.052 Uiso 1 1 calc R . . H50B H 0.5744 0.9929 0.6765 0.052 Uiso 1 1 calc R . . H50C H 0.5619 0.9987 0.8743 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.02371(16) 0.01510(15) 0.02430(17) 0.00138(11) -0.00449(12) -0.00183(11) C1 0.0144(19) 0.023(2) 0.018(2) -0.0025(16) -0.0005(15) 0.0007(16) C2 0.019(2) 0.031(2) 0.016(2) -0.0038(17) 0.0044(16) -0.0037(17) C3 0.022(2) 0.025(2) 0.0112(19) 0.0001(16) -0.0030(16) -0.0077(17) C4 0.018(2) 0.026(2) 0.018(2) -0.0001(17) -0.0005(16) -0.0009(17) C5 0.016(2) 0.026(2) 0.015(2) -0.0018(16) 0.0046(16) 0.0021(16) C6 0.0128(18) 0.0190(19) 0.015(2) -0.0006(15) -0.0008(15) -0.0039(15) C7 0.0138(19) 0.024(2) 0.0134(19) -0.0007(16) 0.0022(15) -0.0033(16) N1 0.0140(16) 0.0162(16) 0.0109(15) 0.0005(12) 0.0005(12) 0.0004(12) C8 0.021(2) 0.0161(19) 0.0078(17) 0.0002(14) 0.0029(15) -0.0019(15) C9 0.0177(19) 0.0181(19) 0.0089(18) 0.0003(14) 0.0002(15) 0.0000(15) C10 0.025(2) 0.021(2) 0.015(2) 0.0005(16) -0.0004(17) 0.0066(17) C11 0.038(3) 0.018(2) 0.013(2) -0.0001(16) 0.0004(18) 0.0059(18) C15 0.054(3) 0.020(2) 0.024(2) -0.0018(18) -0.001(2) 0.008(2) C12 0.035(2) 0.018(2) 0.014(2) -0.0017(16) 0.0038(18) -0.0041(18) C16 0.054(3) 0.020(2) 0.022(2) 0.0006(18) 0.001(2) -0.008(2) C13 0.025(2) 0.021(2) 0.0123(19) 0.0011(15) 0.0010(16) -0.0037(17) C14 0.022(2) 0.0149(19) 0.0086(18) 0.0001(14) 0.0010(15) 0.0034(15) N2 0.0160(16) 0.0150(16) 0.0078(15) 0.0001(12) 0.0013(12) 0.0005(12) C17 0.0137(18) 0.0198(19) 0.016(2) 0.0021(16) 0.0008(15) 0.0031(15) C18 0.0159(19) 0.0157(18) 0.0101(18) 0.0017(14) -0.0011(15) 0.0039(14) C19 0.0166(19) 0.0172(19) 0.0149(19) 0.0017(15) 0.0004(15) -0.0004(15) C20 0.020(2) 0.024(2) 0.0110(19) 0.0024(15) 0.0070(16) 0.0030(16) C21 0.025(2) 0.021(2) 0.0101(19) -0.0021(15) -0.0004(16) 0.0052(16) C22 0.019(2) 0.026(2) 0.019(2) 0.0001(17) -0.0015(17) -0.0029(17) C23 0.018(2) 0.025(2) 0.020(2) 0.0013(17) 0.0030(17) -0.0029(17) O1 0.0342(18) 0.0285(17) 0.0211(16) -0.0036(13) 0.0042(14) 0.0047(14) O2 0.033(2) 0.050(2) 0.031(2) 0.0114(17) 0.0054(16) -0.0069(17) C24 0.025(2) 0.020(2) 0.014(2) 0.0004(16) -0.0014(17) -0.0002(17) C25 0.091(5) 0.020(3) 0.039(3) -0.003(2) 0.016(3) -0.007(3) Ag2 0.01895(15) 0.01482(14) 0.01976(15) 0.00064(11) 0.00042(11) -0.00155(10) C26 0.0145(19) 0.021(2) 0.017(2) 0.0008(16) 0.0014(15) -0.0008(15) C27 0.018(2) 0.026(2) 0.016(2) 0.0024(16) 0.0051(16) 0.0031(16) C28 0.026(2) 0.019(2) 0.0105(19) -0.0003(15) -0.0008(16) 0.0034(16) C29 0.019(2) 0.026(2) 0.018(2) -0.0006(17) -0.0015(16) -0.0033(17) C30 0.017(2) 0.026(2) 0.013(2) 0.0011(16) 0.0038(16) -0.0015(16) C31 0.0147(18) 0.0145(18) 0.0114(18) 0.0026(14) 0.0001(14) 0.0036(14) C32 0.0182(19) 0.0179(19) 0.0121(19) 0.0011(15) 0.0034(15) 0.0028(15) N3 0.0137(16) 0.0138(16) 0.0115(16) 0.0003(12) 0.0000(12) 0.0006(12) C33 0.0147(18) 0.0185(19) 0.0072(17) -0.0005(14) 0.0015(14) -0.0004(14) C34 0.0179(19) 0.0145(18) 0.0107(18) 0.0010(14) -0.0012(15) 0.0016(15) C35 0.022(2) 0.020(2) 0.0126(19) -0.0010(15) 0.0005(16) -0.0040(16) C36 0.033(2) 0.017(2) 0.016(2) -0.0001(16) 0.0023(18) -0.0041(17) C40 0.041(3) 0.016(2) 0.026(2) -0.0012(17) 0.001(2) -0.0060(19) C37 0.033(2) 0.016(2) 0.017(2) 0.0009(16) 0.0000(18) 0.0050(17) C41 0.046(3) 0.017(2) 0.026(2) 0.0012(18) 0.001(2) 0.009(2) C38 0.024(2) 0.020(2) 0.0121(19) 0.0011(15) 0.0003(16) 0.0054(17) C39 0.020(2) 0.0155(19) 0.0091(18) -0.0017(14) 0.0029(15) -0.0017(15) N4 0.0153(16) 0.0164(16) 0.0100(15) 0.0000(12) 0.0009(12) 0.0003(13) C42 0.0147(19) 0.024(2) 0.0130(19) -0.0010(15) 0.0040(15) -0.0019(16) C43 0.0139(18) 0.0204(19) 0.0097(18) -0.0011(15) 0.0025(14) -0.0039(15) C44 0.0162(19) 0.023(2) 0.014(2) -0.0008(16) -0.0002(15) 0.0005(16) C45 0.017(2) 0.030(2) 0.013(2) -0.0056(16) 0.0070(16) -0.0030(17) C46 0.023(2) 0.025(2) 0.0116(19) -0.0002(16) -0.0017(16) -0.0075(17) C47 0.019(2) 0.025(2) 0.019(2) 0.0006(17) -0.0002(17) 0.0005(17) C48 0.016(2) 0.026(2) 0.018(2) -0.0020(17) -0.0004(16) 0.0017(16) O3 0.0270(16) 0.0185(15) 0.0209(16) -0.0014(12) 0.0011(13) -0.0004(12) O4 0.0294(18) 0.0386(19) 0.0273(18) 0.0017(15) 0.0105(14) -0.0026(15) C49 0.025(2) 0.019(2) 0.0127(19) 0.0008(15) -0.0044(16) 0.0001(16) C50 0.056(3) 0.022(2) 0.030(3) -0.004(2) 0.014(2) -0.003(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 Ag1 C8 2.073(4) . ? Ag1 O1 2.171(3) . ? C1 C2 1.384(6) . ? C1 C6 1.390(6) . ? C1 H1 0.9500 . ? C2 C3 1.384(6) . ? C2 H2 0.9500 . ? C3 C4 1.379(6) . ? C3 H3 0.9500 . ? C4 C5 1.395(6) . ? C4 H4 0.9500 . ? C5 C6 1.385(6) . ? C5 H5 0.9500 . ? C6 C7 1.515(5) . ? C7 N1 1.465(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N1 C8 1.358(5) . ? N1 C9 1.395(5) . ? C8 N2 1.354(5) . ? C9 C10 1.390(6) . ? C9 C14 1.391(6) . ? C10 C11 1.392(6) . ? C10 H10 0.9500 . ? C11 C12 1.415(7) . ? C11 C15 1.507(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C12 C13 1.393(6) . ? C12 C16 1.505(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C13 C14 1.389(6) . ? C13 H13 0.9500 . ? C14 N2 1.394(5) . ? N2 C17 1.459(5) . ? C17 C18 1.514(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C23 1.391(6) . ? C18 C19 1.392(6) . ? C19 C20 1.389(6) . ? C19 H19 0.9500 . ? C20 C21 1.389(6) . ? C20 H20 0.9500 . ? C21 C22 1.388(6) . ? C21 H21 0.9500 . ? C22 C23 1.385(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? O1 C24 1.271(5) . ? O2 C24 1.235(6) . ? C24 C25 1.497(6) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? Ag2 C33 2.073(4) . ? Ag2 O3 2.137(3) . ? C26 C31 1.383(6) . ? C26 C27 1.387(6) . ? C26 H26 0.9500 . ? C27 C28 1.384(6) . ? C27 H27 0.9500 . ? C28 C29 1.387(6) . ? C28 H28 0.9500 . ? C29 C30 1.399(6) . ? C29 H29 0.9500 . ? C30 C31 1.385(6) . ? C30 H30 0.9500 . ? C31 C32 1.513(5) . ? C32 N3 1.458(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? N3 C33 1.359(5) . ? N3 C34 1.398(5) . ? C33 N4 1.361(5) . ? C34 C39 1.390(6) . ? C34 C35 1.393(6) . ? C35 C36 1.382(6) . ? C35 H35 0.9500 . ? C36 C37 1.421(6) . ? C36 C40 1.507(6) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C37 C38 1.391(6) . ? C37 C41 1.513(6) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C38 C39 1.392(6) . ? C38 H38 0.9500 . ? C39 N4 1.391(5) . ? N4 C42 1.464(5) . ? C42 C43 1.517(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.385(6) . ? C43 C48 1.390(6) . ? C44 C45 1.385(6) . ? C44 H44 0.9500 . ? C45 C46 1.388(6) . ? C45 H45 0.9500 . ? C46 C47 1.389(6) . ? C46 H46 0.9500 . ? C47 C48 1.388(6) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? O3 C49 1.281(5) . ? O4 C49 1.242(6) . ? C49 C50 1.511(6) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? 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 C8 Ag1 O1 165.38(15) . . ? C2 C1 C6 119.7(4) . . ? C2 C1 H1 120.2 . . ? C6 C1 H1 120.2 . . ? C3 C2 C1 120.5(4) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.4(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.7(4) . . ? C5 C6 C7 119.9(4) . . ? C1 C6 C7 120.3(4) . . ? N1 C7 C6 112.9(3) . . ? N1 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C8 N1 C9 110.8(3) . . ? C8 N1 C7 125.7(3) . . ? C9 N1 C7 123.5(3) . . ? N2 C8 N1 106.0(3) . . ? N2 C8 Ag1 129.5(3) . . ? N1 C8 Ag1 124.4(3) . . ? C10 C9 C14 121.8(4) . . ? C10 C9 N1 132.0(4) . . ? C14 C9 N1 106.1(3) . . ? C9 C10 C11 117.4(4) . . ? C9 C10 H10 121.3 . . ? C11 C10 H10 121.3 . . ? C10 C11 C12 121.0(4) . . ? C10 C11 C15 119.0(4) . . ? C12 C11 C15 120.0(4) . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C12 C11 120.9(4) . . ? C13 C12 C16 119.0(4) . . ? C11 C12 C16 120.1(4) . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C13 C12 117.7(4) . . ? C14 C13 H13 121.2 . . ? C12 C13 H13 121.2 . . ? C13 C14 C9 121.3(4) . . ? C13 C14 N2 132.6(4) . . ? C9 C14 N2 106.1(3) . . ? C8 N2 C14 111.0(3) . . ? C8 N2 C17 125.9(3) . . ? C14 N2 C17 123.1(3) . . ? N2 C17 C18 113.1(3) . . ? N2 C17 H17A 109.0 . . ? C18 C17 H17A 109.0 . . ? N2 C17 H17B 109.0 . . ? C18 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C23 C18 C19 119.2(4) . . ? C23 C18 C17 120.3(4) . . ? C19 C18 C17 120.5(4) . . ? C20 C19 C18 120.3(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 119.1(4) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 120.7(4) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C18 120.3(4) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? C24 O1 Ag1 106.6(3) . . ? O2 C24 O1 122.7(4) . . ? O2 C24 C25 119.6(5) . . ? O1 C24 C25 117.7(5) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C33 Ag2 O3 166.60(14) . . ? C31 C26 C27 120.4(4) . . ? C31 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 120.1(4) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 119.9(4) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C28 C29 C30 119.7(4) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C31 C30 C29 120.1(4) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C26 C31 C30 119.7(4) . . ? C26 C31 C32 120.5(4) . . ? C30 C31 C32 119.7(4) . . ? N3 C32 C31 113.2(3) . . ? N3 C32 H32A 108.9 . . ? C31 C32 H32A 108.9 . . ? N3 C32 H32B 108.9 . . ? C31 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C33 N3 C34 110.7(3) . . ? C33 N3 C32 125.8(3) . . ? C34 N3 C32 123.4(3) . . ? N3 C33 N4 106.0(3) . . ? N3 C33 Ag2 128.3(3) . . ? N4 C33 Ag2 125.6(3) . . ? C39 C34 C35 121.9(4) . . ? C39 C34 N3 106.2(3) . . ? C35 C34 N3 131.9(4) . . ? C36 C35 C34 117.4(4) . . ? C36 C35 H35 121.3 . . ? C34 C35 H35 121.3 . . ? C35 C36 C37 121.1(4) . . ? C35 C36 C40 119.4(4) . . ? C37 C36 C40 119.5(4) . . ? C36 C40 H40A 109.5 . . ? C36 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C36 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C38 C37 C36 120.8(4) . . ? C38 C37 C41 119.0(4) . . ? C36 C37 C41 120.2(4) . . ? C37 C41 H41A 109.5 . . ? C37 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C37 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C37 C38 C39 117.7(4) . . ? C37 C38 H38 121.2 . . ? C39 C38 H38 121.2 . . ? C34 C39 N4 106.4(3) . . ? C34 C39 C38 121.1(4) . . ? N4 C39 C38 132.5(4) . . ? C33 N4 C39 110.8(3) . . ? C33 N4 C42 125.6(3) . . ? C39 N4 C42 123.6(3) . . ? N4 C42 C43 112.6(3) . . ? N4 C42 H42A 109.1 . . ? C43 C42 H42A 109.1 . . ? N4 C42 H42B 109.1 . . ? C43 C42 H42B 109.1 . . ? H42A C42 H42B 107.8 . . ? C44 C43 C48 119.4(4) . . ? C44 C43 C42 121.0(4) . . ? C48 C43 C42 119.5(4) . . ? C43 C44 C45 120.2(4) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? C44 C45 C46 120.6(4) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? C45 C46 C47 119.4(4) . . ? C45 C46 H46 120.3 . . ? C47 C46 H46 120.3 . . ? C48 C47 C46 120.0(4) . . ? C48 C47 H47 120.0 . . ? C46 C47 H47 120.0 . . ? C47 C48 C43 120.4(4) . . ? C47 C48 H48 119.8 . . ? C43 C48 H48 119.8 . . ? C49 O3 Ag2 109.7(3) . . ? O4 C49 O3 123.8(4) . . ? O4 C49 C50 119.9(4) . . ? O3 C49 C50 116.2(4) . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? 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 C6 C1 C2 C3 -0.5(6) . . . . ? C1 C2 C3 C4 -0.9(7) . . . . ? C2 C3 C4 C5 1.6(6) . . . . ? C3 C4 C5 C6 -1.0(6) . . . . ? C4 C5 C6 C1 -0.4(6) . . . . ? C4 C5 C6 C7 -179.2(4) . . . . ? C2 C1 C6 C5 1.1(6) . . . . ? C2 C1 C6 C7 180.0(4) . . . . ? C5 C6 C7 N1 -125.1(4) . . . . ? C1 C6 C7 N1 56.1(5) . . . . ? C6 C7 N1 C8 -115.4(4) . . . . ? C6 C7 N1 C9 62.8(5) . . . . ? C9 N1 C8 N2 0.0(4) . . . . ? C7 N1 C8 N2 178.3(3) . . . . ? C9 N1 C8 Ag1 175.8(3) . . . . ? C7 N1 C8 Ag1 -5.8(5) . . . . ? O1 Ag1 C8 N2 129.2(5) . . . . ? O1 Ag1 C8 N1 -45.6(7) . . . . ? C8 N1 C9 C10 -179.6(4) . . . . ? C7 N1 C9 C10 2.1(7) . . . . ? C8 N1 C9 C14 0.6(4) . . . . ? C7 N1 C9 C14 -177.8(3) . . . . ? C14 C9 C10 C11 0.9(6) . . . . ? N1 C9 C10 C11 -179.0(4) . . . . ? C9 C10 C11 C12 0.5(6) . . . . ? C9 C10 C11 C15 179.8(4) . . . . ? C10 C11 C12 C13 -1.1(7) . . . . ? C15 C11 C12 C13 179.6(4) . . . . ? C10 C11 C12 C16 179.4(4) . . . . ? C15 C11 C12 C16 0.2(7) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? C16 C12 C13 C14 179.9(4) . . . . ? C12 C13 C14 C9 0.9(6) . . . . ? C12 C13 C14 N2 179.8(4) . . . . ? C10 C9 C14 C13 -1.6(6) . . . . ? N1 C9 C14 C13 178.3(4) . . . . ? C10 C9 C14 N2 179.3(4) . . . . ? N1 C9 C14 N2 -0.9(4) . . . . ? N1 C8 N2 C14 -0.5(4) . . . . ? Ag1 C8 N2 C14 -176.1(3) . . . . ? N1 C8 N2 C17 178.0(3) . . . . ? Ag1 C8 N2 C17 2.4(6) . . . . ? C13 C14 N2 C8 -178.1(4) . . . . ? C9 C14 N2 C8 0.9(4) . . . . ? C13 C14 N2 C17 3.3(7) . . . . ? C9 C14 N2 C17 -177.7(3) . . . . ? C8 N2 C17 C18 -112.8(4) . . . . ? C14 N2 C17 C18 65.6(5) . . . . ? N2 C17 C18 C23 -127.5(4) . . . . ? N2 C17 C18 C19 53.8(5) . . . . ? C23 C18 C19 C20 0.9(6) . . . . ? C17 C18 C19 C20 179.6(4) . . . . ? C18 C19 C20 C21 -0.9(6) . . . . ? C19 C20 C21 C22 0.2(6) . . . . ? C20 C21 C22 C23 0.5(6) . . . . ? C21 C22 C23 C18 -0.5(7) . . . . ? C19 C18 C23 C22 -0.2(6) . . . . ? C17 C18 C23 C22 -178.9(4) . . . . ? C8 Ag1 O1 C24 166.6(5) . . . . ? Ag1 O1 C24 O2 1.2(5) . . . . ? Ag1 O1 C24 C25 179.5(4) . . . . ? C31 C26 C27 C28 1.2(6) . . . . ? C26 C27 C28 C29 -0.1(6) . . . . ? C27 C28 C29 C30 -1.1(6) . . . . ? C28 C29 C30 C31 1.3(6) . . . . ? C27 C26 C31 C30 -1.0(6) . . . . ? C27 C26 C31 C32 179.9(4) . . . . ? C29 C30 C31 C26 -0.3(6) . . . . ? C29 C30 C31 C32 178.9(4) . . . . ? C26 C31 C32 N3 -53.2(5) . . . . ? C30 C31 C32 N3 127.6(4) . . . . ? C31 C32 N3 C33 112.1(4) . . . . ? C31 C32 N3 C34 -64.2(5) . . . . ? C34 N3 C33 N4 -0.4(4) . . . . ? C32 N3 C33 N4 -177.1(3) . . . . ? C34 N3 C33 Ag2 175.2(3) . . . . ? C32 N3 C33 Ag2 -1.6(6) . . . . ? O3 Ag2 C33 N3 -126.8(5) . . . . ? O3 Ag2 C33 N4 47.9(8) . . . . ? C33 N3 C34 C39 0.0(4) . . . . ? C32 N3 C34 C39 176.8(3) . . . . ? C33 N3 C34 C35 179.4(4) . . . . ? C32 N3 C34 C35 -3.7(7) . . . . ? C39 C34 C35 C36 -1.9(6) . . . . ? N3 C34 C35 C36 178.7(4) . . . . ? C34 C35 C36 C37 0.7(6) . . . . ? C34 C35 C36 C40 -179.2(4) . . . . ? C35 C36 C37 C38 0.6(7) . . . . ? C40 C36 C37 C38 -179.5(4) . . . . ? C35 C36 C37 C41 -178.8(4) . . . . ? C40 C36 C37 C41 1.1(7) . . . . ? C36 C37 C38 C39 -0.8(6) . . . . ? C41 C37 C38 C39 178.6(4) . . . . ? C35 C34 C39 N4 -179.1(4) . . . . ? N3 C34 C39 N4 0.4(4) . . . . ? C35 C34 C39 C38 1.7(6) . . . . ? N3 C34 C39 C38 -178.8(4) . . . . ? C37 C38 C39 C34 -0.3(6) . . . . ? C37 C38 C39 N4 -179.2(4) . . . . ? N3 C33 N4 C39 0.6(4) . . . . ? Ag2 C33 N4 C39 -175.1(3) . . . . ? N3 C33 N4 C42 -179.3(3) . . . . ? Ag2 C33 N4 C42 5.0(5) . . . . ? C34 C39 N4 C33 -0.7(4) . . . . ? C38 C39 N4 C33 178.4(4) . . . . ? C34 C39 N4 C42 179.2(3) . . . . ? C38 C39 N4 C42 -1.7(7) . . . . ? C33 N4 C42 C43 116.0(4) . . . . ? C39 N4 C42 C43 -63.9(5) . . . . ? N4 C42 C43 C44 -56.0(5) . . . . ? N4 C42 C43 C48 125.4(4) . . . . ? C48 C43 C44 C45 -1.0(6) . . . . ? C42 C43 C44 C45 -179.5(4) . . . . ? C43 C44 C45 C46 1.1(6) . . . . ? C44 C45 C46 C47 0.1(6) . . . . ? C45 C46 C47 C48 -1.4(6) . . . . ? C46 C47 C48 C43 1.5(7) . . . . ? C44 C43 C48 C47 -0.3(6) . . . . ? C42 C43 C48 C47 178.2(4) . . . . ? C33 Ag2 O3 C49 -172.4(5) . . . . ? Ag2 O3 C49 O4 0.5(5) . . . . ? Ag2 O3 C49 C50 -179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 76.95 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 3.974 _refine_diff_density_min -2.735 _refine_diff_density_rms 0.112