# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6chinolinaurea-ag_11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 Ag N7 O5' _chemical_formula_weight 696.47 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9856(7) _cell_length_b 16.9749(10) _cell_length_c 27.0605(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5964.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4455 _cell_measurement_theta_min 2.7439 _cell_measurement_theta_max 29.2877 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2832 _exptl_absorpt_coefficient_mu 0.730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93045 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25623 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_unetI/netI 0.0638 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 29.35 _reflns_number_total 7150 _reflns_number_gt 3643 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -51.00 28.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -38.0000 60.0000 79 #__ type_ start__ end____ width___ exp.time_ 2 omega 37.00 74.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 179.0000 0.0000 37 #__ type_ start__ end____ width___ exp.time_ 3 omega 44.00 82.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 179.0000 90.0000 38 #__ type_ start__ end____ width___ exp.time_ 4 omega -25.00 40.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 38.0000 -150.0000 65 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7150 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1418 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag 0.50639(2) 0.129380(18) 0.374160(11) 0.06200(13) Uani 1 1 d . . . O3 O 0.0318(2) 0.78070(18) 0.41312(10) 0.0772(9) Uani 1 1 d . . . O4 O 0.0035(2) 0.89099(17) 0.37576(13) 0.0901(10) Uani 1 1 d . . . O5 O -0.0224(2) 0.78023(18) 0.33868(10) 0.0727(8) Uani 1 1 d . . . N7 N 0.0046(2) 0.8176(2) 0.37582(15) 0.0587(8) Uani 1 1 d . . . O1 O 0.0763(2) -0.07948(16) 0.18871(9) 0.0705(9) Uani 1 1 d . . . C1 C 0.5138(3) 0.1289(2) 0.26131(14) 0.0537(10) Uani 1 1 d . . . H1 H 0.5734 0.1578 0.2674 0.064 Uiso 1 1 calc R . . C2 C 0.4886(3) 0.1120(3) 0.21278(15) 0.0623(12) Uani 1 1 d . . . H2 H 0.5300 0.1296 0.1870 0.075 Uiso 1 1 calc R . . C3 C 0.4022(3) 0.0692(2) 0.20341(13) 0.0590(11) Uani 1 1 d . . . H3 H 0.3852 0.0565 0.1710 0.071 Uiso 1 1 calc R . . C4 C 0.3384(3) 0.04412(19) 0.24232(12) 0.0444(9) Uani 1 1 d . . . C5 C 0.3707(3) 0.0640(2) 0.29068(12) 0.0427(9) Uani 1 1 d . . . C6 C 0.3084(3) 0.0399(2) 0.33040(13) 0.0565(11) Uani 1 1 d . . . H6 H 0.3276 0.0531 0.3625 0.068 Uiso 1 1 calc R . . C7 C 0.2215(3) -0.0017(2) 0.32297(13) 0.0570(11) Uani 1 1 d . . . H7 H 0.1816 -0.0165 0.3499 0.068 Uiso 1 1 calc R . . C8 C 0.1900(3) -0.0233(2) 0.27490(13) 0.0479(9) Uani 1 1 d . . . C9 C 0.2477(2) 0.00001(19) 0.23534(14) 0.0476(12) Uani 1 1 d . . . H9 H 0.2269 -0.0134 0.2035 0.057 Uiso 1 1 calc R . . C10 C 0.0497(3) -0.0946(2) 0.23068(15) 0.0494(10) Uani 1 1 d . . . C11 C -0.0892(3) -0.1870(2) 0.16204(15) 0.0701(12) Uani 1 1 d . . . H11 H -0.0294 -0.1687 0.1470 0.084 Uiso 1 1 calc R . . C12 C -0.1644(4) -0.2254(3) 0.13435(18) 0.0910(16) Uani 1 1 d . . . H12 H -0.1555 -0.2320 0.1005 0.109 Uiso 1 1 calc R . . C13 C -0.2516(4) -0.2537(3) 0.1568(2) 0.0886(19) Uani 1 1 d . . . H13 H -0.3008 -0.2802 0.1382 0.106 Uiso 1 1 calc R . . C14 C -0.2667(4) -0.2432(2) 0.2062(2) 0.0842(17) Uani 1 1 d . . . H14 H -0.3262 -0.2620 0.2212 0.101 Uiso 1 1 calc R . . C15 C -0.1934(3) -0.2046(2) 0.23342(16) 0.0658(12) Uani 1 1 d . . . H15 H -0.2038 -0.1973 0.2671 0.079 Uiso 1 1 calc R . . C16 C -0.1042(3) -0.1765(2) 0.21179(15) 0.0532(10) Uani 1 1 d . . . N1 N 0.4579(2) 0.10615(17) 0.29955(10) 0.0483(8) Uani 1 1 d . . . H2N H 0.071(3) -0.077(2) 0.2991(12) 0.073(14) Uiso 1 1 d . . . N2 N 0.1000(2) -0.0678(2) 0.27197(12) 0.0541(9) Uani 1 1 d . . . N3 N -0.0324(3) -0.1402(2) 0.24306(14) 0.0599(10) Uani 1 1 d . . . H3N H -0.044(3) -0.142(2) 0.2723(13) 0.062(14) Uiso 1 1 d . . . O2 O 0.9252(2) -0.08475(17) 0.56265(9) 0.0762(9) Uani 1 1 d . . . C17 C 0.4944(3) 0.1285(2) 0.48647(15) 0.0590(11) Uani 1 1 d . . . H17 H 0.4356 0.1580 0.4798 0.071 Uiso 1 1 calc R . . C18 C 0.5205(3) 0.1145(2) 0.53581(15) 0.0619(11) Uani 1 1 d . . . H18 H 0.4797 0.1339 0.5613 0.074 Uiso 1 1 calc R . . C19 C 0.6067(3) 0.0720(2) 0.54583(13) 0.0590(11) Uani 1 1 d . . . H19 H 0.6251 0.0622 0.5785 0.071 Uiso 1 1 calc R . . C20 C 0.6680(3) 0.0427(2) 0.50743(12) 0.0430(9) Uani 1 1 d . . . C21 C 0.6349(3) 0.0585(2) 0.45838(12) 0.0447(9) Uani 1 1 d . . . C22 C 0.6924(3) 0.0278(2) 0.41927(12) 0.0548(10) Uani 1 1 d . . . H22 H 0.6702 0.0359 0.3870 0.066 Uiso 1 1 calc R . . C23 C 0.7790(3) -0.0131(2) 0.42741(12) 0.0530(10) Uani 1 1 d . . . H23 H 0.8159 -0.0329 0.4007 0.064 Uiso 1 1 calc R . . C24 C 0.8155(3) -0.0268(2) 0.47601(12) 0.0431(9) Uani 1 1 d . . . C25 C 0.7585(3) -0.00008(19) 0.51516(13) 0.0462(11) Uani 1 1 d . . . H25 H 0.7802 -0.0105 0.5472 0.055 Uiso 1 1 calc R . . C26 C 0.9549(3) -0.0981(2) 0.52127(14) 0.0491(10) Uani 1 1 d . . . C27 C 1.1080(3) -0.1815(2) 0.54128(14) 0.0512(10) Uani 1 1 d . . . C28 C 1.0920(3) -0.1898(2) 0.59122(14) 0.0694(12) Uani 1 1 d . . . H28 H 1.0346 -0.1676 0.6063 0.083 Uiso 1 1 calc R . . C29 C 1.1629(4) -0.2318(3) 0.61844(18) 0.0901(15) Uani 1 1 d . . . H29 H 1.1522 -0.2378 0.6522 0.108 Uiso 1 1 calc R . . C30 C 1.2480(4) -0.2646(3) 0.5977(2) 0.0945(19) Uani 1 1 d . . . H30 H 1.2951 -0.2922 0.6169 0.113 Uiso 1 1 calc R . . C31 C 1.2627(4) -0.2561(3) 0.5483(2) 0.0848(17) Uani 1 1 d . . . H31 H 1.3201 -0.2790 0.5335 0.102 Uiso 1 1 calc R . . C32 C 1.1946(3) -0.2147(2) 0.51977(16) 0.0644(12) Uani 1 1 d . . . H32 H 1.2063 -0.2088 0.4861 0.077 Uiso 1 1 calc R . . N4 N 0.5490(2) 0.10187(17) 0.44882(10) 0.0490(8) Uani 1 1 d . . . N5 N 0.9075(3) -0.0685(2) 0.47971(12) 0.0508(9) Uani 1 1 d . . . H5N H 0.931(2) -0.0754(19) 0.4547(10) 0.035(11) Uiso 1 1 d . . . N6 N 1.0393(3) -0.1417(2) 0.50974(13) 0.0576(10) Uani 1 1 d . . . H6N H 1.050(3) -0.1464(19) 0.4820(11) 0.035(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0564(2) 0.0720(2) 0.05764(19) 0.0008(2) -0.02283(14) 0.00294(19) O3 0.099(2) 0.080(2) 0.0526(18) 0.0069(18) 0.0098(16) -0.007(2) O4 0.120(3) 0.0513(18) 0.098(2) -0.001(2) 0.0409(18) -0.0063(19) O5 0.088(2) 0.076(2) 0.0543(17) -0.0093(17) 0.0075(15) -0.0037(18) N7 0.059(2) 0.060(2) 0.057(2) 0.000(2) 0.0270(17) -0.007(2) O1 0.068(2) 0.091(2) 0.0527(16) 0.0066(16) -0.0057(14) -0.0333(18) C1 0.045(2) 0.047(2) 0.069(3) 0.002(2) -0.0107(19) -0.010(2) C2 0.057(3) 0.070(3) 0.059(3) 0.004(2) 0.0025(19) -0.012(2) C3 0.060(3) 0.069(3) 0.048(2) -0.002(2) 0.0001(19) -0.013(2) C4 0.048(2) 0.042(2) 0.044(2) 0.0041(18) -0.0036(17) -0.0002(19) C5 0.046(2) 0.034(2) 0.048(2) 0.0086(18) -0.0107(17) -0.0005(18) C6 0.071(3) 0.057(3) 0.041(2) 0.000(2) -0.0133(19) -0.011(2) C7 0.064(3) 0.064(3) 0.043(2) 0.006(2) 0.000(2) -0.012(2) C8 0.049(2) 0.043(2) 0.051(2) 0.0019(19) -0.0051(18) -0.003(2) C9 0.047(3) 0.053(3) 0.043(3) -0.0014(17) -0.0077(16) -0.012(2) C10 0.043(2) 0.045(2) 0.061(3) 0.005(2) -0.005(2) -0.002(2) C11 0.061(3) 0.075(3) 0.073(3) 0.009(3) -0.017(2) -0.022(3) C12 0.095(4) 0.090(4) 0.088(4) 0.019(3) -0.030(3) -0.026(3) C13 0.071(4) 0.067(4) 0.128(5) 0.010(3) -0.043(3) -0.023(3) C14 0.045(3) 0.059(3) 0.149(5) 0.009(3) -0.003(3) -0.011(2) C15 0.049(3) 0.050(3) 0.098(3) 0.002(2) 0.001(2) -0.009(2) C16 0.043(2) 0.039(2) 0.077(3) 0.005(2) -0.013(2) -0.0016(19) N1 0.0497(19) 0.0409(18) 0.0543(18) 0.0064(16) -0.0153(15) -0.0053(16) N2 0.050(2) 0.061(2) 0.051(2) 0.0023(19) 0.0005(17) -0.0144(18) N3 0.051(2) 0.071(3) 0.058(2) 0.003(2) -0.0020(18) -0.0174(19) O2 0.081(2) 0.102(2) 0.0463(16) 0.0033(16) -0.0006(14) 0.0413(19) C17 0.053(3) 0.054(3) 0.070(3) -0.005(2) -0.010(2) 0.010(2) C18 0.065(3) 0.063(3) 0.057(3) -0.005(2) 0.005(2) 0.012(2) C19 0.071(3) 0.059(3) 0.047(2) 0.000(2) 0.002(2) 0.015(2) C20 0.052(2) 0.034(2) 0.043(2) 0.0008(17) -0.0018(17) 0.0009(19) C21 0.046(2) 0.041(2) 0.047(2) -0.0005(19) -0.0078(17) 0.0002(19) C22 0.068(3) 0.062(3) 0.034(2) -0.004(2) -0.0078(18) 0.011(2) C23 0.063(3) 0.058(3) 0.038(2) -0.0006(19) 0.005(2) 0.015(2) C24 0.046(2) 0.039(2) 0.044(2) 0.0025(18) -0.0052(17) 0.0029(19) C25 0.057(3) 0.044(3) 0.037(2) 0.0008(17) -0.0049(15) 0.003(2) C26 0.041(2) 0.048(2) 0.058(3) 0.000(2) -0.0042(19) 0.004(2) C27 0.042(2) 0.043(2) 0.068(3) -0.008(2) -0.0129(19) -0.0003(19) C28 0.066(3) 0.078(3) 0.064(3) -0.006(3) -0.012(2) 0.023(3) C29 0.089(4) 0.099(4) 0.082(4) 0.010(3) -0.025(3) 0.025(3) C30 0.071(4) 0.087(4) 0.126(5) 0.011(4) -0.035(3) 0.023(3) C31 0.049(3) 0.071(4) 0.134(5) -0.008(3) -0.007(3) 0.012(2) C32 0.045(3) 0.055(3) 0.093(3) -0.006(2) -0.003(2) 0.002(2) N4 0.0497(19) 0.0446(18) 0.0526(18) -0.0055(16) -0.0091(15) 0.0034(16) N5 0.054(2) 0.057(2) 0.041(2) 0.0014(18) 0.0052(16) 0.0099(18) N6 0.053(2) 0.071(3) 0.049(2) -0.009(2) -0.0049(17) 0.014(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 N4 2.146(3) . ? Ag1 N1 2.151(3) . ? O3 N7 1.239(4) . ? O4 N7 1.246(4) . ? O5 N7 1.239(4) . ? O1 C10 1.215(4) . ? C1 N1 1.322(4) . ? C1 C2 1.384(5) . ? C2 C3 1.360(5) . ? C3 C4 1.406(4) . ? C4 C5 1.415(4) . ? C4 C9 1.408(4) . ? C5 N1 1.361(4) . ? C5 C6 1.406(4) . ? C6 C7 1.346(5) . ? C7 C8 1.412(4) . ? C8 C9 1.365(4) . ? C8 N2 1.395(4) . ? C10 N3 1.360(5) . ? C10 N2 1.372(4) . ? C11 C16 1.372(5) . ? C11 C12 1.394(5) . ? C12 C13 1.371(6) . ? C13 C14 1.362(6) . ? C14 C15 1.371(5) . ? C15 C16 1.383(5) . ? C16 N3 1.402(5) . ? O2 C26 1.206(4) . ? C17 N4 1.322(4) . ? C17 C18 1.398(5) . ? C18 C19 1.359(5) . ? C19 C20 1.400(4) . ? C20 C25 1.397(4) . ? C20 C21 1.420(4) . ? C21 N4 1.362(4) . ? C21 C22 1.396(4) . ? C22 C23 1.340(5) . ? C23 C24 1.417(4) . ? C24 C25 1.370(4) . ? C24 N5 1.392(4) . ? C26 N6 1.358(5) . ? C26 N5 1.377(4) . ? C27 C28 1.374(5) . ? C27 C32 1.385(5) . ? C27 N6 1.408(4) . ? C28 C29 1.378(5) . ? C29 C30 1.358(6) . ? C30 C31 1.359(6) . ? C31 C32 1.368(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ag1 N1 156.79(11) . . ? O5 N7 O3 118.9(3) . . ? O5 N7 O4 120.5(4) . . ? O3 N7 O4 120.6(4) . . ? N1 C1 C2 123.5(3) . . ? C3 C2 C1 118.9(4) . . ? C2 C3 C4 120.6(4) . . ? C3 C4 C5 116.4(3) . . ? C3 C4 C9 123.6(3) . . ? C5 C4 C9 119.9(3) . . ? N1 C5 C6 119.8(3) . . ? N1 C5 C4 122.4(3) . . ? C6 C5 C4 117.8(3) . . ? C7 C6 C5 121.4(3) . . ? C6 C7 C8 121.1(4) . . ? C9 C8 C7 119.2(4) . . ? C9 C8 N2 124.9(3) . . ? C7 C8 N2 115.9(3) . . ? C8 C9 C4 120.5(3) . . ? O1 C10 N3 125.0(4) . . ? O1 C10 N2 123.8(4) . . ? N3 C10 N2 111.2(3) . . ? C16 C11 C12 119.2(4) . . ? C13 C12 C11 120.3(5) . . ? C14 C13 C12 120.5(5) . . ? C15 C14 C13 119.4(5) . . ? C14 C15 C16 121.3(4) . . ? C11 C16 C15 119.3(4) . . ? C11 C16 N3 123.7(4) . . ? C15 C16 N3 117.0(4) . . ? C1 N1 C5 118.2(3) . . ? C1 N1 Ag1 121.3(2) . . ? C5 N1 Ag1 120.4(2) . . ? C10 N2 C8 128.7(3) . . ? C10 N3 C16 128.5(4) . . ? N4 C17 C18 123.2(4) . . ? C19 C18 C17 118.7(4) . . ? C18 C19 C20 120.6(3) . . ? C19 C20 C25 123.5(3) . . ? C19 C20 C21 117.1(3) . . ? C25 C20 C21 119.4(3) . . ? N4 C21 C22 119.7(3) . . ? N4 C21 C20 121.8(3) . . ? C22 C21 C20 118.5(3) . . ? C23 C22 C21 121.2(3) . . ? C22 C23 C24 121.2(3) . . ? C25 C24 N5 125.2(3) . . ? C25 C24 C23 118.9(3) . . ? N5 C24 C23 115.9(3) . . ? C24 C25 C20 120.7(3) . . ? O2 C26 N6 125.0(4) . . ? O2 C26 N5 123.1(4) . . ? N6 C26 N5 111.8(3) . . ? C28 C27 C32 119.6(4) . . ? C28 C27 N6 123.3(4) . . ? C32 C27 N6 117.1(4) . . ? C29 C28 C27 118.5(4) . . ? C30 C29 C28 122.3(5) . . ? C31 C30 C29 118.5(5) . . ? C30 C31 C32 121.2(5) . . ? C31 C32 C27 119.8(4) . . ? C17 N4 C21 118.6(3) . . ? C17 N4 Ag1 120.8(3) . . ? C21 N4 Ag1 120.5(2) . . ? C26 N5 C24 128.9(3) . . ? C26 N6 C27 129.3(4) . . ? _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.333 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 949683' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ag-pq6u-etoh_4_r1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 Ag N7 O5' _chemical_formula_weight 696.47 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4802(6) _cell_length_b 10.7958(10) _cell_length_c 15.5706(9) _cell_angle_alpha 86.193(6) _cell_angle_beta 85.546(6) _cell_angle_gamma 87.377(7) _cell_volume 1416.87(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1829 _cell_measurement_theta_min 2.6241 _cell_measurement_theta_max 32.7835 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.768 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99422 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16091 _diffrn_reflns_av_R_equivalents 0.0725 _diffrn_reflns_av_unetI/netI 0.1856 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 32.86 _reflns_number_total 9317 _reflns_number_gt 3082 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -32.00 44.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 -57.0000 150.0000 76 #__ type_ start__ end____ width___ exp.time_ 2 omega 47.00 104.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 179.0000 -180.0000 57 #__ type_ start__ end____ width___ exp.time_ 3 omega 14.00 67.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 -99.0000 -90.0000 53 #__ type_ start__ end____ width___ exp.time_ 4 omega 42.00 68.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 -99.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega -3.00 23.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 77.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega 9.00 93.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 57.0000 30.0000 84 #__ type_ start__ end____ width___ exp.time_ 7 omega -46.00 70.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 27.4081 -19.0000 -150.0000 116 ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0101P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00045(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9317 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2429 _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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 C1 C 1.0955(6) 0.6304(5) 0.2570(3) 0.0486(14) Uani 1 1 d . . . H1 H 1.0711 0.6348 0.3160 0.058 Uiso 1 1 calc R . . C2 C 1.2296(6) 0.5594(4) 0.2299(3) 0.0487(14) Uani 1 1 d . . . H2 H 1.2953 0.5216 0.2699 0.058 Uiso 1 1 calc R . . C3 C 1.2628(6) 0.5461(5) 0.1433(3) 0.0454(13) Uani 1 1 d . . . H3 H 1.3499 0.4971 0.1243 0.055 Uiso 1 1 calc R . . C4 C 1.1655(5) 0.6065(4) 0.0836(3) 0.0398(12) Uani 1 1 d . . . C5 C 1.0385(5) 0.6840(4) 0.1171(3) 0.0380(12) Uani 1 1 d . . . C6 C 0.9484(5) 0.7538(5) 0.0584(3) 0.0444(13) Uani 1 1 d . . . H6 H 0.8711 0.8107 0.0789 0.053 Uiso 1 1 calc R . . C7 C 0.9713(5) 0.7406(4) -0.0278(3) 0.0432(13) Uani 1 1 d . . . H7 H 0.9083 0.7873 -0.0653 0.052 Uiso 1 1 calc R . . C8 C 1.0901(6) 0.6564(4) -0.0612(3) 0.0407(13) Uani 1 1 d . . . C9 C 1.1869(6) 0.5929(4) -0.0061(3) 0.0424(13) Uani 1 1 d . . . H9 H 1.2678 0.5401 -0.0279 0.051 Uiso 1 1 calc R . . C10 C 1.2047(6) 0.5804(5) -0.2012(3) 0.0444(13) Uani 1 1 d . . . C11 C 1.2456(6) 0.5219(5) -0.3533(3) 0.0488(14) Uani 1 1 d . . . C12 C 1.3755(6) 0.4420(5) -0.3451(3) 0.0539(15) Uani 1 1 d . . . H12 H 1.4262 0.4354 -0.2941 0.065 Uiso 1 1 calc R . . C13 C 1.4312(7) 0.3707(5) -0.4137(4) 0.0669(18) Uani 1 1 d . . . H13 H 1.5182 0.3161 -0.4078 0.080 Uiso 1 1 calc R . . C14 C 1.3588(8) 0.3805(6) -0.4895(4) 0.073(2) Uani 1 1 d . . . H14 H 1.3951 0.3322 -0.5348 0.087 Uiso 1 1 calc R . . C15 C 1.2326(7) 0.4622(6) -0.4976(4) 0.079(2) Uani 1 1 d . . . H15 H 1.1838 0.4701 -0.5492 0.094 Uiso 1 1 calc R . . C16 C 1.1765(6) 0.5327(6) -0.4313(3) 0.0656(18) Uani 1 1 d . . . H16 H 1.0911 0.5886 -0.4386 0.079 Uiso 1 1 calc R . . C17 C 0.4181(6) 0.8897(5) 0.2715(3) 0.0479(14) Uani 1 1 d . . . H17 H 0.4453 0.8906 0.3281 0.058 Uiso 1 1 calc R . . C18 C 0.2812(6) 0.9569(5) 0.2483(3) 0.0462(14) Uani 1 1 d . . . H18 H 0.2165 0.9974 0.2896 0.055 Uiso 1 1 calc R . . C19 C 0.2442(6) 0.9623(4) 0.1650(3) 0.0440(13) Uani 1 1 d . . . H19 H 0.1548 1.0082 0.1486 0.053 Uiso 1 1 calc R . . C20 C 0.3411(5) 0.8984(4) 0.1030(3) 0.0365(12) Uani 1 1 d . . . C21 C 0.4709(5) 0.8254(4) 0.1337(3) 0.0374(12) Uani 1 1 d . . . C22 C 0.5622(5) 0.7519(5) 0.0753(3) 0.0441(13) Uani 1 1 d . . . H22 H 0.6424 0.6981 0.0948 0.053 Uiso 1 1 calc R . . C23 C 0.5329(6) 0.7599(4) -0.0092(3) 0.0440(13) Uani 1 1 d . . . H23 H 0.5948 0.7115 -0.0471 0.053 Uiso 1 1 calc R . . C24 C 0.4116(5) 0.8393(4) -0.0416(3) 0.0373(12) Uani 1 1 d . . . C25 C 0.3139(5) 0.9059(4) 0.0151(3) 0.0424(13) Uani 1 1 d . . . H25 H 0.2304 0.9557 -0.0049 0.051 Uiso 1 1 calc R . . C26 C 0.2957(6) 0.9091(5) -0.1802(3) 0.0445(13) Uani 1 1 d . . . C27 C 0.2562(6) 0.9572(5) -0.3350(3) 0.0439(13) Uani 1 1 d . . . C28 C 0.3253(7) 0.9433(6) -0.4174(3) 0.073(2) Uani 1 1 d . . . H28 H 0.4101 0.8864 -0.4254 0.088 Uiso 1 1 calc R . . C29 C 0.2720(7) 1.0108(7) -0.4871(4) 0.080(2) Uani 1 1 d . . . H29 H 0.3205 0.9988 -0.5417 0.095 Uiso 1 1 calc R . . C30 C 0.1484(7) 1.0959(6) -0.4782(3) 0.0687(18) Uani 1 1 d . . . H30 H 0.1143 1.1437 -0.5256 0.082 Uiso 1 1 calc R . . C31 C 0.0765(7) 1.1087(5) -0.3974(3) 0.0617(17) Uani 1 1 d . . . H31 H -0.0095 1.1647 -0.3905 0.074 Uiso 1 1 calc R . . C32 C 0.1278(6) 1.0410(5) -0.3258(3) 0.0524(15) Uani 1 1 d . . . H32 H 0.0765 1.0514 -0.2716 0.063 Uiso 1 1 calc R . . Ag1 Ag 0.75560(5) 0.75777(5) 0.24719(3) 0.06784(19) Uani 1 1 d . . . N1 N 1.0016(5) 0.6914(4) 0.2040(2) 0.0449(11) Uani 1 1 d . . . N2 N 1.0961(5) 0.6476(4) -0.1512(3) 0.0467(12) Uani 1 1 d . . . N3 N 1.1781(6) 0.5937(5) -0.2868(3) 0.0517(13) Uani 1 1 d . . . N4 N 0.5116(4) 0.8245(4) 0.2168(2) 0.0440(11) Uani 1 1 d . . . N5 N 0.4013(5) 0.8421(4) -0.1314(3) 0.0459(12) Uani 1 1 d . . . N6 N 0.3222(5) 0.8875(4) -0.2662(3) 0.0470(12) Uani 1 1 d . . . N7 N 0.2493(6) 0.2578(4) 0.2759(3) 0.0572(13) Uani 1 1 d . . . O1 O 1.3127(4) 0.5173(4) -0.1723(2) 0.0653(12) Uani 1 1 d . . . O2 O 0.1888(4) 0.9766(3) -0.14938(19) 0.0544(10) Uani 1 1 d . . . O3 O 0.3763(5) 0.2463(4) 0.3094(3) 0.0961(17) Uani 1 1 d . . . O4 O 0.2478(5) 0.2563(4) 0.1976(2) 0.0850(15) Uani 1 1 d . . . O5 O 0.1262(5) 0.2733(4) 0.3210(3) 0.0957(16) Uani 1 1 d . . . H2N H 1.026(5) 0.688(4) -0.175(3) 0.041(15) Uiso 1 1 d . . . H3N H 1.106(5) 0.637(4) -0.297(3) 0.033(15) Uiso 1 1 d . . . H5N H 0.470(6) 0.806(5) -0.157(3) 0.062(18) Uiso 1 1 d . . . H6N H 0.427(8) 0.838(6) -0.276(4) 0.15(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(3) 0.055(4) 0.046(3) -0.003(3) -0.008(3) -0.005(3) C2 0.044(3) 0.044(4) 0.058(3) 0.004(3) -0.011(3) 0.003(3) C3 0.039(3) 0.043(4) 0.054(3) -0.007(3) -0.001(3) 0.003(2) C4 0.037(3) 0.031(3) 0.052(3) -0.002(3) -0.005(2) -0.006(2) C5 0.038(3) 0.031(3) 0.045(3) -0.001(2) -0.001(2) -0.004(2) C6 0.037(3) 0.047(4) 0.049(3) -0.006(3) -0.001(2) 0.010(2) C7 0.038(3) 0.044(3) 0.047(3) 0.002(3) -0.006(2) 0.009(2) C8 0.039(3) 0.038(3) 0.045(3) -0.004(3) 0.000(2) 0.002(2) C9 0.038(3) 0.039(3) 0.050(3) -0.006(3) -0.003(2) -0.001(2) C10 0.046(3) 0.045(4) 0.042(3) -0.003(3) 0.000(3) -0.005(3) C11 0.048(3) 0.056(4) 0.043(3) -0.012(3) 0.005(3) -0.003(3) C12 0.050(4) 0.061(4) 0.048(3) 0.001(3) 0.004(3) 0.003(3) C13 0.074(4) 0.055(4) 0.067(4) -0.009(4) 0.019(4) 0.005(3) C14 0.091(5) 0.078(5) 0.049(4) -0.017(4) 0.015(4) -0.016(4) C15 0.068(5) 0.120(7) 0.048(4) -0.018(4) -0.003(3) -0.003(4) C16 0.055(4) 0.096(5) 0.046(3) -0.003(4) -0.006(3) 0.005(3) C17 0.048(3) 0.053(4) 0.043(3) -0.001(3) -0.002(3) -0.008(3) C18 0.045(3) 0.047(4) 0.045(3) -0.006(3) 0.003(3) 0.003(3) C19 0.038(3) 0.045(3) 0.048(3) -0.003(3) -0.004(2) 0.005(2) C20 0.032(3) 0.038(3) 0.040(3) -0.001(2) -0.002(2) -0.006(2) C21 0.032(3) 0.037(3) 0.044(3) -0.003(3) -0.002(2) -0.005(2) C22 0.035(3) 0.046(4) 0.051(3) -0.006(3) -0.008(2) 0.008(2) C23 0.042(3) 0.038(3) 0.052(3) -0.007(3) -0.006(3) 0.011(2) C24 0.032(3) 0.041(3) 0.039(3) -0.005(2) -0.001(2) -0.003(2) C25 0.040(3) 0.037(3) 0.049(3) 0.001(3) -0.007(2) 0.008(2) C26 0.044(3) 0.042(4) 0.048(3) -0.002(3) -0.003(3) -0.005(3) C27 0.039(3) 0.052(4) 0.042(3) -0.011(3) -0.008(2) -0.001(3) C28 0.068(4) 0.111(6) 0.040(3) -0.018(4) -0.006(3) 0.025(4) C29 0.072(5) 0.128(7) 0.038(3) -0.014(4) 0.001(3) 0.005(4) C30 0.071(5) 0.088(5) 0.046(4) 0.010(3) -0.010(3) -0.009(4) C31 0.059(4) 0.069(5) 0.058(4) -0.007(4) -0.016(3) 0.004(3) C32 0.051(4) 0.065(4) 0.041(3) -0.002(3) -0.005(3) -0.001(3) Ag1 0.0426(3) 0.1016(4) 0.0580(3) -0.0069(3) -0.0065(2) 0.0178(2) N1 0.040(3) 0.051(3) 0.043(2) -0.005(2) -0.002(2) 0.003(2) N2 0.050(3) 0.045(3) 0.045(3) -0.003(2) -0.006(2) 0.011(2) N3 0.045(3) 0.058(4) 0.051(3) -0.005(3) -0.009(2) 0.019(3) N4 0.037(2) 0.055(3) 0.041(2) -0.007(2) -0.004(2) 0.000(2) N5 0.043(3) 0.051(3) 0.043(3) -0.009(2) 0.000(2) 0.010(2) N6 0.046(3) 0.057(3) 0.037(2) -0.005(2) -0.005(2) 0.007(2) N7 0.058(3) 0.059(4) 0.054(3) -0.008(3) -0.006(3) 0.013(3) O1 0.063(3) 0.081(3) 0.049(2) -0.007(2) -0.008(2) 0.033(2) O2 0.056(2) 0.065(3) 0.041(2) -0.0076(19) -0.0047(18) 0.019(2) O3 0.065(3) 0.124(4) 0.105(3) -0.052(3) -0.032(3) 0.042(3) O4 0.138(4) 0.066(3) 0.051(2) -0.011(2) -0.014(3) 0.017(3) O5 0.066(3) 0.125(4) 0.083(3) 0.032(3) 0.020(3) 0.038(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.316(6) . ? C1 C2 1.395(6) . ? C2 C3 1.371(6) . ? C3 C4 1.400(7) . ? C4 C9 1.411(6) . ? C4 C5 1.421(6) . ? C5 N1 1.371(5) . ? C5 C6 1.397(6) . ? C6 C7 1.357(5) . ? C7 C8 1.418(5) . ? C8 C9 1.363(6) . ? C8 N2 1.408(6) . ? C10 O1 1.213(6) . ? C10 N3 1.365(6) . ? C10 N2 1.372(6) . ? C11 C12 1.376(7) . ? C11 C16 1.384(7) . ? C11 N3 1.406(6) . ? C12 C13 1.398(6) . ? C13 C14 1.368(7) . ? C14 C15 1.363(8) . ? C15 C16 1.366(6) . ? C17 N4 1.331(5) . ? C17 C18 1.399(6) . ? C18 C19 1.356(6) . ? C19 C20 1.413(5) . ? C20 C25 1.401(6) . ? C20 C21 1.419(6) . ? C21 N4 1.365(5) . ? C21 C22 1.409(5) . ? C22 C23 1.354(6) . ? C23 C24 1.410(6) . ? C24 C25 1.379(5) . ? C24 N5 1.406(6) . ? C26 O2 1.226(5) . ? C26 N5 1.369(6) . ? C26 N6 1.373(6) . ? C27 C32 1.388(6) . ? C27 C28 1.383(6) . ? C27 N6 1.405(6) . ? C28 C29 1.362(8) . ? C29 C30 1.367(7) . ? C30 C31 1.368(6) . ? C31 C32 1.380(7) . ? Ag1 N4 2.235(4) . ? Ag1 N1 2.242(4) . ? N7 O5 1.223(5) . ? N7 O4 1.222(5) . ? N7 O3 1.230(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.8(5) . . ? C3 C2 C1 119.0(5) . . ? C2 C3 C4 119.9(4) . . ? C3 C4 C9 123.5(4) . . ? C3 C4 C5 116.9(4) . . ? C9 C4 C5 119.6(5) . . ? N1 C5 C6 119.6(4) . . ? N1 C5 C4 122.5(5) . . ? C6 C5 C4 118.0(4) . . ? C7 C6 C5 121.5(4) . . ? C6 C7 C8 120.7(5) . . ? C9 C8 N2 126.0(4) . . ? C9 C8 C7 119.2(4) . . ? N2 C8 C7 114.8(5) . . ? C8 C9 C4 120.7(4) . . ? O1 C10 N3 124.1(5) . . ? O1 C10 N2 123.5(5) . . ? N3 C10 N2 112.5(5) . . ? C12 C11 C16 118.6(4) . . ? C12 C11 N3 123.8(5) . . ? C16 C11 N3 117.7(5) . . ? C11 C12 C13 119.9(5) . . ? C14 C13 C12 120.6(6) . . ? C13 C14 C15 118.9(5) . . ? C14 C15 C16 121.3(6) . . ? C15 C16 C11 120.6(6) . . ? N4 C17 C18 123.6(5) . . ? C19 C18 C17 119.1(4) . . ? C18 C19 C20 120.2(5) . . ? C25 C20 C19 122.8(4) . . ? C25 C20 C21 120.6(4) . . ? C19 C20 C21 116.6(4) . . ? N4 C21 C22 118.9(4) . . ? N4 C21 C20 122.8(4) . . ? C22 C21 C20 118.3(4) . . ? C23 C22 C21 119.9(4) . . ? C22 C23 C24 122.1(4) . . ? C25 C24 C23 119.1(4) . . ? C25 C24 N5 125.5(5) . . ? C23 C24 N5 115.5(4) . . ? C24 C25 C20 119.7(4) . . ? O2 C26 N5 123.2(5) . . ? O2 C26 N6 125.1(5) . . ? N5 C26 N6 111.6(4) . . ? C32 C27 C28 117.6(5) . . ? C32 C27 N6 124.4(4) . . ? C28 C27 N6 118.0(5) . . ? C29 C28 C27 121.5(6) . . ? C28 C29 C30 121.2(5) . . ? C31 C30 C29 118.0(6) . . ? C30 C31 C32 121.9(6) . . ? C31 C32 C27 119.8(5) . . ? N4 Ag1 N1 150.39(13) . . ? C1 N1 C5 117.6(4) . . ? C1 N1 Ag1 122.1(3) . . ? C5 N1 Ag1 117.8(3) . . ? C10 N2 C8 127.3(5) . . ? C10 N3 C11 127.5(5) . . ? C17 N4 C21 117.4(4) . . ? C17 N4 Ag1 121.7(3) . . ? C21 N4 Ag1 119.0(3) . . ? C26 N5 C24 128.3(4) . . ? C26 N6 C27 126.1(5) . . ? O5 N7 O4 120.6(5) . . ? O5 N7 O3 119.8(5) . . ? O4 N7 O3 119.5(5) . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.330 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 949684' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ag(pq6u)2no3_an_3r3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H29 Ag N8 O5' _chemical_formula_weight 737.52 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3672(2) _cell_length_b 9.0123(4) _cell_length_c 25.5246(8) _cell_angle_alpha 85.865(3) _cell_angle_beta 87.607(3) _cell_angle_gamma 69.359(3) _cell_volume 1581.56(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4561 _cell_measurement_theta_min 2.8124 _cell_measurement_theta_max 29.2736 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.694 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92832 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23963 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_unetI/netI 0.1098 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 29.34 _reflns_number_total 7541 _reflns_number_gt 4541 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -33.00 50.25 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -82.0000 129.0000 111 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 51.00 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 77.0000 120.0000 84 #__ type_ start__ end____ width___ exp.time_ 3 omega -12.00 87.00 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 77.0000 -90.0000 132 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 35.00 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -38.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 5 omega -7.00 87.50 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 38.0000 60.0000 126 #__ type_ start__ end____ width___ exp.time_ 6 omega 21.00 89.25 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 38.0000 -180.0000 91 #__ type_ start__ end____ width___ exp.time_ 7 omega -51.00 21.00 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -38.0000 -120.0000 96 #__ type_ start__ end____ width___ exp.time_ 8 omega 3.00 74.25 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -124.0000 26.0000 95 #__ type_ start__ end____ width___ exp.time_ 9 omega -82.00 -4.00 0.7500 25.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 134.0000 115.0000 104 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELTXL _computing_publication_material SHELTXL _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^ > 2\s(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^)+(0.0622P)^2^+0.2081P] 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 7541 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1654 _refine_ls_R_factor_gt 0.0966 _refine_ls_wR_factor_ref 0.1728 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 C1 C 1.8216(8) -0.1286(7) 0.3049(2) 0.0423(14) Uani 1 1 d . . . C2 C 1.9608(10) -0.2714(9) 0.3199(3) 0.0570(19) Uani 1 1 d . . . C3 C 1.8722(9) -0.0228(8) 0.2711(2) 0.0497(16) Uani 1 1 d . . . H3 H 1.7778 0.0724 0.2596 0.060 Uiso 1 1 calc R . . C4 C 0.0603(10) 0.9432(10) 0.2542(2) 0.0617(19) Uani 1 1 d . . . H4 H 0.0935 1.0165 0.2321 0.074 Uiso 1 1 calc R . . C5 C 0.1994(10) 0.8026(10) 0.2696(3) 0.067(2) Uani 1 1 d . . . H5 H 0.3271 0.7798 0.2579 0.081 Uiso 1 1 calc R . . C6 C 0.1504(9) 0.6954(9) 0.3023(3) 0.065(2) Uani 1 1 d . . . H6 H 0.2451 0.5993 0.3128 0.078 Uiso 1 1 calc R . . C7 C 1.5479(8) -0.1504(7) 0.3634(2) 0.0408(14) Uani 1 1 d . . . C8 C 1.2284(7) -0.1000(7) 0.40799(19) 0.0367(13) Uani 1 1 d . . . C9 C 1.2752(8) -0.2240(7) 0.4453(2) 0.0399(14) Uani 1 1 d . . . H9 H 1.4038 -0.2908 0.4488 0.048 Uiso 1 1 calc R . . C10 C 1.1305(8) -0.2513(7) 0.4784(2) 0.0382(13) Uani 1 1 d . . . C11 C 0.9353(8) -0.1486(7) 0.4730(2) 0.0366(13) Uani 1 1 d . . . C12 C 0.8892(7) -0.0227(7) 0.4348(2) 0.0398(14) Uani 1 1 d . . . H12 H 0.7613 0.0450 0.4308 0.048 Uiso 1 1 calc R . . C13 C 1.0313(8) 0.0007(7) 0.4034(2) 0.0421(14) Uani 1 1 d . . . H13 H 0.9986 0.0852 0.3782 0.051 Uiso 1 1 calc R . . C14 C 1.1701(9) -0.3746(7) 0.5181(2) 0.0527(16) Uani 1 1 d . . . H14 H 1.2962 -0.4457 0.5226 0.063 Uiso 1 1 calc R . . C15 C 1.0249(10) -0.3898(8) 0.5499(3) 0.0623(19) Uani 1 1 d . . . H15 H 1.0514 -0.4695 0.5768 0.075 Uiso 1 1 calc R . . C16 C 0.8376(9) -0.2867(8) 0.5421(2) 0.0527(16) Uani 1 1 d . . . H16 H 0.7395 -0.3009 0.5637 0.063 Uiso 1 1 calc R . . C17 C -0.0123(6) 0.7615(6) 0.03440(12) 0.0617(19) Uani 1 1 d G . . H17 H -0.0503 0.7788 -0.0005 0.074 Uiso 1 1 calc R . . C18 C 0.0831(6) 0.6078(5) 0.05515(13) 0.0503(16) Uani 1 1 d G . . H18 H 0.1088 0.5223 0.0342 0.060 Uiso 1 1 calc R . . C19 C 0.1400(5) 0.5819(4) 0.10726(14) 0.0406(14) Uani 1 1 d G . . C20 C 0.1015(6) 0.7098(5) 0.13862(11) 0.0483(15) Uani 1 1 d G . . H20 H 0.1395 0.6925 0.1735 0.058 Uiso 1 1 calc R . . C21 C 0.0061(6) 0.8635(4) 0.11787(17) 0.0591(18) Uani 1 1 d G . . H21 H -0.0196 0.9490 0.1388 0.071 Uiso 1 1 calc R . . C22 C -0.0507(6) 0.8893(4) 0.06576(18) 0.067(2) Uani 1 1 d G . . H22 H -0.1145 0.9922 0.0519 0.080 Uiso 1 1 calc R . . C23 C 0.3249(8) 0.2946(7) 0.1062(2) 0.0421(14) Uani 1 1 d . . . C24 C 0.4646(7) 0.8186(7) 0.0558(2) 0.0370(13) Uani 1 1 d . . . H24 H 0.4375 0.7999 0.0221 0.044 Uiso 1 1 calc R . . C25 C 0.4083(8) 0.9689(7) 0.0704(2) 0.0408(14) Uani 1 1 d . . . H25 H 0.3432 1.0525 0.0468 0.049 Uiso 1 1 calc R . . C26 C 0.4472(7) 1.0013(7) 0.1215(2) 0.0354(13) Uani 1 1 d . . . C27 C 0.5463(8) 0.8785(7) 0.1553(2) 0.0410(14) Uani 1 1 d . . . H27 H 0.5739 0.8995 0.1886 0.049 Uiso 1 1 calc R . . C28 C 0.6073(7) 0.7219(7) 0.14104(19) 0.0351(13) Uani 1 1 d . . . C29 C 0.5627(7) 0.6903(6) 0.09015(19) 0.0317(12) Uani 1 1 d . . . C30 C 0.7613(9) 0.4397(8) 0.1571(2) 0.0548(17) Uani 1 1 d . . . H30 H 0.8294 0.3522 0.1789 0.066 Uiso 1 1 calc R . . C31 C 0.7096(8) 0.4181(7) 0.1071(2) 0.0454(15) Uani 1 1 d . . . H31 H 0.7442 0.3152 0.0963 0.054 Uiso 1 1 calc R . . C32 C 0.7125(8) 0.5878(8) 0.1739(2) 0.0477(15) Uani 1 1 d . . . H32 H 0.7483 0.6019 0.2072 0.057 Uiso 1 1 calc R . . C33 C 0.6746(11) 0.4274(10) 0.3079(3) 0.082(2) Uani 1 1 d . . . H33A H 0.8138 0.3831 0.3069 0.123 Uiso 1 1 calc R . . H33B H 0.6338 0.5403 0.3104 0.123 Uiso 1 1 calc R . . H33C H 0.6247 0.4050 0.2764 0.123 Uiso 1 1 calc R . . C34 C 0.6030(10) 0.3590(9) 0.3523(3) 0.067(2) Uani 1 1 d . . . Ag1 Ag 0.5000 0.0000 0.5000 0.0534(2) Uani 1 2 d S . . Ag2 Ag 0.5000 0.5000 0.0000 0.0509(2) Uani 1 2 d S . . N1 N 0.7900(6) -0.1679(6) 0.50524(17) 0.0443(12) Uani 1 1 d . . . N2 N 1.3601(6) -0.0583(6) 0.37461(17) 0.0450(13) Uani 1 1 d . . . H2N H 1.3187 0.0356 0.3594 0.054 Uiso 1 1 calc R . . N3 N 1.6248(7) -0.0845(7) 0.32255(19) 0.0497(14) Uani 1 1 d . . . N4 N 0.6130(6) 0.5385(6) 0.07416(17) 0.0399(11) Uani 1 1 d . . . N5 N 0.3800(8) 1.1582(6) 0.1381(2) 0.0479(14) Uani 1 1 d . . . N6 N 0.2296(7) 0.4284(6) 0.13143(19) 0.0440(12) Uani 1 1 d . . . N7 N 0.2225(7) 0.2708(6) 0.27013(19) 0.0486(13) Uani 1 1 d . . . N8 N 0.5467(10) 0.3058(11) 0.3869(3) 0.125(3) Uani 1 1 d . . . O1 O 1.6345(5) -0.2740(5) 0.38718(17) 0.0589(12) Uani 1 1 d . . . O2 O 0.3596(7) 0.2940(5) 0.05886(15) 0.0595(12) Uani 1 1 d . . . O3 O 0.3850(6) 0.1881(6) 0.25296(16) 0.0684(14) Uani 1 1 d . . . O4 O 0.1764(6) 0.2526(6) 0.31634(16) 0.0677(14) Uani 1 1 d . . . O5 O 0.1092(7) 0.3710(6) 0.24003(16) 0.0763(15) Uani 1 1 d . . . H2 H 1.935(12) -0.330(10) 0.335(3) 0.092 Uiso 1 1 d . . . H3N H 1.560(7) -0.002(6) 0.3059(19) 0.031(15) Uiso 1 1 d . . . H5N H 0.382(7) 1.170(6) 0.170(2) 0.032(16) Uiso 1 1 d . . . H6N H 0.208(7) 0.415(7) 0.165(2) 0.045(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.031(3) 0.052(4) 0.041(3) -0.006(3) 0.002(2) -0.011(3) C2 0.043(4) 0.059(5) 0.061(5) -0.003(4) 0.010(3) -0.009(4) C3 0.051(4) 0.057(4) 0.042(3) 0.001(3) 0.000(3) -0.021(3) C4 0.060(4) 0.086(6) 0.053(4) -0.010(4) 0.012(3) -0.043(4) C5 0.044(4) 0.103(7) 0.062(5) -0.024(4) 0.016(3) -0.034(4) C6 0.041(4) 0.074(5) 0.072(5) -0.004(4) 0.009(3) -0.009(4) C7 0.038(3) 0.044(4) 0.037(3) -0.001(3) 0.003(3) -0.011(3) C8 0.034(3) 0.042(4) 0.032(3) -0.004(3) 0.001(2) -0.012(3) C9 0.036(3) 0.034(3) 0.043(3) 0.002(3) -0.001(3) -0.005(3) C10 0.043(3) 0.035(3) 0.035(3) -0.002(3) 0.000(3) -0.012(3) C11 0.037(3) 0.046(4) 0.028(3) -0.008(3) 0.002(2) -0.016(3) C12 0.029(3) 0.047(4) 0.035(3) -0.003(3) -0.001(2) -0.002(3) C13 0.042(3) 0.046(4) 0.032(3) 0.000(3) -0.003(3) -0.007(3) C14 0.048(4) 0.046(4) 0.054(4) 0.005(3) 0.004(3) -0.005(3) C15 0.067(5) 0.056(5) 0.057(4) 0.015(3) 0.000(3) -0.016(4) C16 0.053(4) 0.059(5) 0.050(4) -0.007(3) 0.015(3) -0.025(4) C17 0.051(4) 0.071(5) 0.058(4) 0.015(4) -0.017(3) -0.017(4) C18 0.048(4) 0.060(5) 0.042(4) -0.003(3) -0.006(3) -0.018(3) C19 0.033(3) 0.049(4) 0.041(3) -0.001(3) 0.004(2) -0.016(3) C20 0.050(4) 0.052(4) 0.042(3) -0.004(3) 0.006(3) -0.018(3) C21 0.056(4) 0.041(4) 0.076(5) -0.002(4) 0.009(4) -0.013(3) C22 0.053(4) 0.058(5) 0.087(5) 0.023(4) -0.006(4) -0.020(4) C23 0.052(4) 0.040(4) 0.040(3) -0.002(3) 0.005(3) -0.024(3) C24 0.038(3) 0.037(3) 0.034(3) -0.002(3) 0.001(2) -0.011(3) C25 0.040(3) 0.046(4) 0.030(3) 0.003(3) -0.004(2) -0.007(3) C26 0.041(3) 0.038(3) 0.030(3) -0.006(3) 0.007(2) -0.017(3) C27 0.049(3) 0.054(4) 0.025(3) 0.001(3) -0.001(2) -0.026(3) C28 0.040(3) 0.043(4) 0.026(3) 0.001(2) 0.000(2) -0.020(3) C29 0.027(3) 0.035(3) 0.034(3) -0.001(2) 0.004(2) -0.012(2) C30 0.064(4) 0.044(4) 0.053(4) 0.018(3) -0.013(3) -0.018(3) C31 0.049(3) 0.035(3) 0.049(4) 0.006(3) -0.005(3) -0.011(3) C32 0.056(4) 0.055(4) 0.031(3) 0.005(3) -0.010(3) -0.019(3) C33 0.079(5) 0.083(6) 0.080(5) -0.001(5) 0.017(4) -0.025(5) C34 0.046(4) 0.067(5) 0.080(5) 0.028(4) -0.014(4) -0.014(4) Ag1 0.0339(4) 0.0737(6) 0.0503(4) -0.0071(4) 0.0062(3) -0.0162(4) Ag2 0.0762(5) 0.0358(4) 0.0439(4) -0.0012(3) -0.0135(3) -0.0227(4) N1 0.045(3) 0.049(3) 0.039(3) -0.006(2) 0.004(2) -0.017(3) N2 0.038(3) 0.044(3) 0.040(3) 0.011(2) 0.008(2) -0.002(2) N3 0.035(3) 0.056(4) 0.046(3) 0.016(3) 0.001(2) -0.004(3) N4 0.046(3) 0.038(3) 0.039(3) -0.002(2) -0.003(2) -0.018(2) N5 0.068(4) 0.044(3) 0.028(3) -0.009(3) 0.003(3) -0.014(3) N6 0.056(3) 0.039(3) 0.031(3) -0.004(2) 0.007(2) -0.009(3) N7 0.051(3) 0.053(3) 0.038(3) 0.002(3) -0.005(3) -0.015(3) N8 0.071(5) 0.152(8) 0.132(7) 0.088(6) -0.015(4) -0.033(5) O1 0.040(2) 0.053(3) 0.069(3) 0.017(2) 0.010(2) -0.003(2) O2 0.100(3) 0.043(3) 0.036(2) -0.010(2) 0.022(2) -0.027(3) O3 0.047(3) 0.089(4) 0.047(3) -0.001(3) 0.002(2) 0.002(3) O4 0.074(3) 0.076(4) 0.036(2) 0.015(2) 0.004(2) -0.008(3) O5 0.067(3) 0.082(4) 0.050(3) 0.021(3) -0.004(2) 0.007(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.373(9) . ? C1 C3 1.379(8) . ? C1 N3 1.423(7) . ? C2 C6 1.384(9) 1_745 ? C3 C4 1.367(8) 1_745 ? C4 C5 1.363(10) . ? C4 C3 1.367(8) 1_365 ? C5 C6 1.366(10) . ? C6 C2 1.384(9) 1_365 ? C7 O1 1.205(6) . ? C7 N3 1.363(7) . ? C7 N2 1.370(7) . ? C8 C9 1.369(7) . ? C8 N2 1.397(7) . ? C8 C13 1.420(7) . ? C9 C10 1.412(7) . ? C10 C14 1.409(8) . ? C10 C11 1.415(7) . ? C11 N1 1.376(7) . ? C11 C12 1.396(7) . ? C12 C13 1.357(7) . ? C14 C15 1.354(8) . ? C15 C16 1.378(8) . ? C16 N1 1.332(7) . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? C19 N6 1.413(5) . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C23 O2 1.223(6) . ? C23 N6 1.357(7) . ? C23 N5 1.369(7) 1_545 ? C24 C25 1.346(7) . ? C24 C29 1.395(7) . ? C25 C26 1.419(7) . ? C26 C27 1.359(7) . ? C26 N5 1.415(7) . ? C27 C28 1.393(8) . ? C28 C32 1.418(8) . ? C28 C29 1.425(7) . ? C29 N4 1.373(7) . ? C30 C32 1.352(8) . ? C30 C31 1.392(8) . ? C31 N4 1.329(7) . ? C33 C34 1.422(10) . ? C34 N8 1.110(9) . ? Ag1 N1 2.141(5) 2_656 ? Ag1 N1 2.141(5) . ? Ag2 N4 2.197(4) 2_665 ? Ag2 N4 2.197(4) . ? N5 C23 1.369(7) 1_565 ? N7 O4 1.230(6) . ? N7 O5 1.235(6) . ? N7 O3 1.247(6) . ? 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 C3 119.2(5) . . ? C2 C1 N3 122.8(6) . . ? C3 C1 N3 118.0(5) . . ? C1 C2 C6 119.7(6) . 1_745 ? C4 C3 C1 120.4(6) 1_745 . ? C5 C4 C3 120.5(7) . 1_365 ? C4 C5 C6 119.6(6) . . ? C5 C6 C2 120.5(7) . 1_365 ? O1 C7 N3 124.3(5) . . ? O1 C7 N2 123.8(5) . . ? N3 C7 N2 111.9(5) . . ? C9 C8 N2 125.5(5) . . ? C9 C8 C13 118.6(5) . . ? N2 C8 C13 115.8(5) . . ? C8 C9 C10 120.7(5) . . ? C14 C10 C9 123.3(5) . . ? C14 C10 C11 117.3(5) . . ? C9 C10 C11 119.4(5) . . ? N1 C11 C12 119.0(5) . . ? N1 C11 C10 121.5(5) . . ? C12 C11 C10 119.4(5) . . ? C13 C12 C11 120.0(5) . . ? C12 C13 C8 121.9(5) . . ? C15 C14 C10 120.1(6) . . ? C14 C15 C16 119.6(6) . . ? N1 C16 C15 123.3(6) . . ? C18 C17 C22 120.0 . . ? C19 C18 C17 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 N6 122.9(3) . . ? C20 C19 N6 117.1(3) . . ? C21 C20 C19 120.0 . . ? C22 C21 C20 120.0 . . ? C21 C22 C17 120.0 . . ? O2 C23 N6 123.5(6) . . ? O2 C23 N5 122.2(6) . 1_545 ? N6 C23 N5 114.3(5) . 1_545 ? C25 C24 C29 121.2(5) . . ? C24 C25 C26 120.7(5) . . ? C27 C26 N5 119.8(5) . . ? C27 C26 C25 119.1(5) . . ? N5 C26 C25 121.1(5) . . ? C26 C27 C28 121.3(5) . . ? C27 C28 C32 124.6(5) . . ? C27 C28 C29 119.1(5) . . ? C32 C28 C29 116.3(5) . . ? N4 C29 C24 119.4(5) . . ? N4 C29 C28 122.2(5) . . ? C24 C29 C28 118.4(5) . . ? C32 C30 C31 120.0(6) . . ? N4 C31 C30 122.7(6) . . ? C30 C32 C28 120.4(5) . . ? N8 C34 C33 179.8(10) . . ? N1 Ag1 N1 180.0(2) 2_656 . ? N4 Ag2 N4 180.00(10) 2_665 . ? C16 N1 C11 118.1(5) . . ? C16 N1 Ag1 121.1(4) . . ? C11 N1 Ag1 120.6(4) . . ? C7 N2 C8 127.2(5) . . ? C7 N3 C1 128.8(5) . . ? C31 N4 C29 118.5(5) . . ? C31 N4 Ag2 121.7(4) . . ? C29 N4 Ag2 119.3(3) . . ? C23 N5 C26 126.1(5) 1_565 . ? C23 N6 C19 125.8(5) . . ? O4 N7 O5 120.7(5) . . ? O4 N7 O3 120.3(5) . . ? O5 N7 O3 119.0(5) . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.045 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 949685' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_s6_dmso- _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9.50 H7 N2 O0.50' _chemical_formula_weight 157.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P22121 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 4.593 _cell_length_b 11.696 _cell_length_c 13.723 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 737.2 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 570 _cell_measurement_theta_min 2.9632 _cell_measurement_theta_max 28.6860 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.087 _exptl_crystal_size_mid 0.074 _exptl_crystal_size_min 0.062 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.89804 _exptl_absorpt_correction_T_max 1.00000 _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) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method OMEGA-SCAN _diffrn_detector_area_resol_mean 16.1314 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2002 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_unetI/netI 0.1181 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.72 _reflns_number_total 1386 _reflns_number_gt 715 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 58.00 83.00 1.0000 170.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 179.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega 37.00 93.00 1.0000 170.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 179.0000 -150.0000 56 #__ type_ start__ end____ width___ exp.time_ 3 omega 35.00 63.00 1.0000 170.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 179.0000 -30.0000 28 #__ type_ start__ end____ width___ exp.time_ 4 omega -50.00 -18.00 1.0000 170.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 -38.0000 0.0000 32 ; _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 'SIR-2004 (GIACOVAZZO, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5(3) _refine_ls_number_reflns 1386 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _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 N1 N 0.1690(6) 0.7243(2) 0.39083(16) 0.0505(9) Uani 1 1 d . . . N2 N 0.1700(6) 0.5575(3) 0.06652(18) 0.0359(7) Uani 1 1 d . . . O1 O 0.5989(6) 0.5000 0.0000 0.0425(8) Uani 1 2 d S . . C1 C -0.0252(8) 0.6482(3) 0.4166(2) 0.0576(11) Uani 1 1 d . . . H1 H -0.0968 0.6522 0.4799 0.069 Uiso 1 1 calc R . . C2 C -0.1335(7) 0.5614(3) 0.3569(2) 0.0480(9) Uani 1 1 d . . . H2 H -0.2691 0.5090 0.3801 0.058 Uiso 1 1 calc R . . C3 C -0.0341(6) 0.5560(2) 0.26337(19) 0.0358(8) Uani 1 1 d . . . H3 H -0.1010 0.4990 0.2217 0.043 Uiso 1 1 calc R . . C4 C 0.1703(4) 0.63683(15) 0.22993(11) 0.0277(7) Uani 1 1 d G . . C5 C 0.2686(4) 0.71722(18) 0.29689(9) 0.0370(9) Uani 1 1 d G . . C6 C 0.4783(5) 0.79672(16) 0.26970(12) 0.0452(9) Uani 1 1 d G . . H6 H 0.5441 0.8505 0.3145 0.054 Uiso 1 1 calc R . . C7 C 0.5899(4) 0.79583(15) 0.17554(14) 0.0426(9) Uani 1 1 d G . . H7 H 0.7302 0.8490 0.1573 0.051 Uiso 1 1 calc R . . C8 C 0.4916(4) 0.71545(16) 0.10857(10) 0.0361(8) Uani 1 1 d G . . H8 H 0.5662 0.7149 0.0456 0.043 Uiso 1 1 calc R . . C9 C 0.2818(4) 0.63595(13) 0.13576(10) 0.0268(8) Uani 1 1 d G . . C10 C 0.3311(10) 0.5000 0.0000 0.0294(10) Uani 1 2 d S . . H2N H -0.022(6) 0.554(3) 0.0661(18) 0.042(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.051(2) 0.067(2) 0.0329(14) -0.0115(14) -0.0009(15) 0.007(2) N2 0.0187(16) 0.0542(16) 0.0347(13) -0.0196(13) 0.0035(13) -0.0011(18) O1 0.0158(18) 0.0533(19) 0.0585(19) -0.0207(16) 0.000 0.000 C1 0.058(3) 0.085(3) 0.030(2) -0.001(2) 0.0096(19) 0.011(3) C2 0.048(2) 0.052(2) 0.0439(18) 0.0006(16) 0.003(2) -0.001(2) C3 0.038(2) 0.0332(17) 0.0364(17) -0.0062(15) 0.0013(16) 0.0025(19) C4 0.0250(19) 0.0287(16) 0.0294(14) -0.0057(14) -0.0023(15) 0.0043(17) C5 0.036(2) 0.0379(18) 0.0371(16) -0.0058(15) -0.0096(16) 0.004(2) C6 0.043(2) 0.0393(19) 0.053(2) -0.0137(16) -0.0157(18) 0.002(2) C7 0.036(2) 0.0341(18) 0.0581(19) 0.0035(16) -0.0031(18) -0.0098(19) C8 0.034(2) 0.0409(17) 0.0336(15) -0.0001(15) -0.0043(15) 0.002(2) C9 0.021(2) 0.0291(16) 0.0300(15) -0.0030(12) -0.0048(14) 0.0040(17) C10 0.026(3) 0.035(2) 0.027(2) 0.000(2) 0.000 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C1 1.309(4) . ? N1 C5 1.370(2) . ? N2 C10 1.354(3) . ? N2 C9 1.417(3) . ? O1 C10 1.230(5) . ? C1 C2 1.396(4) . ? C2 C3 1.364(3) . ? C3 C4 1.410(3) . ? C4 C5 1.3900 . ? C4 C9 1.3900 . ? C5 C6 1.3900 . ? C6 C7 1.3900 . ? C7 C8 1.3900 . ? C8 C9 1.3900 . ? C10 N2 1.354(3) 3_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 116.1(3) . . ? C10 N2 C9 125.1(2) . . ? N1 C1 C2 125.4(3) . . ? C3 C2 C1 117.8(3) . . ? C2 C3 C4 119.9(2) . . ? C5 C4 C9 120.0 . . ? C5 C4 C3 117.06(15) . . ? C9 C4 C3 122.90(15) . . ? N1 C5 C4 123.68(19) . . ? N1 C5 C6 116.32(19) . . ? C4 C5 C6 120.0 . . ? C5 C6 C7 120.0 . . ? C8 C7 C6 120.0 . . ? C7 C8 C9 120.0 . . ? C8 C9 C4 120.0 . . ? C8 C9 N2 120.29(17) . . ? C4 C9 N2 119.64(17) . . ? O1 C10 N2 123.1(2) . 3_565 ? O1 C10 N2 123.1(2) . . ? N2 C10 N2 113.7(4) 3_565 . ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.197 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 949686' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_urea-11r3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N3 O' _chemical_formula_weight 263.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.0204(16) _cell_length_b 4.5893(3) _cell_length_c 11.8276(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.411(7) _cell_angle_gamma 90.00 _cell_volume 1295.68(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 784 _cell_measurement_theta_min 2.9210 _cell_measurement_theta_max 28.9490 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.061 _exptl_crystal_size_mid 0.051 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83783 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method graphite _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4414 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_unetI/netI 0.1064 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 29.01 _reflns_number_total 2641 _reflns_number_gt 1107 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -34.00 1.00 1.0000 310.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -38.0000 0.0000 35 #__ type_ start__ end____ width___ exp.time_ 2 omega -79.00 7.00 1.0000 310.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 -38.0000 -120.0000 86 #__ type_ start__ end____ width___ exp.time_ 3 omega -95.00 -37.00 1.0000 310.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 179.0000 30.0000 58 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0367P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2641 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1881 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1469 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 C1 C 0.39610(15) 0.1592(8) 0.2020(3) 0.0591(11) Uani 1 1 d . . . H1 H 0.3936 0.2315 0.1281 0.071 Uiso 1 1 calc R . . C2 C 0.35790(13) -0.0433(7) 0.2314(3) 0.0437(9) Uani 1 1 d . . . C3 C 0.36279(15) -0.1488(8) 0.3405(3) 0.0579(10) Uani 1 1 d . . . H3 H 0.3367 -0.2830 0.3611 0.069 Uiso 1 1 calc R . . C4 C 0.40554(18) -0.0596(10) 0.4200(3) 0.0756(12) Uani 1 1 d . . . H4 H 0.4093 -0.1381 0.4929 0.091 Uiso 1 1 calc R . . C5 C 0.44223(18) 0.1444(10) 0.3906(4) 0.0780(14) Uani 1 1 d . . . H5 H 0.4705 0.2103 0.4446 0.094 Uiso 1 1 calc R . . C6 C 0.43801(16) 0.2538(9) 0.2828(4) 0.0740(13) Uani 1 1 d . . . H6 H 0.4635 0.3929 0.2637 0.089 Uiso 1 1 calc R . . C7 C 0.05197(15) -0.0491(8) -0.1687(3) 0.0605(10) Uani 1 1 d . . . H7 H 0.0267 0.0294 -0.2259 0.073 Uiso 1 1 calc R . . C8 C 0.07017(15) -0.3408(8) -0.0143(3) 0.0610(11) Uani 1 1 d . . . H8 H 0.0572 -0.4666 0.0385 0.073 Uiso 1 1 calc R . . C9 C 0.12554(14) -0.2760(7) -0.0031(3) 0.0496(10) Uani 1 1 d . . . H9 H 0.1494 -0.3602 0.0552 0.060 Uiso 1 1 calc R . . C10 C 0.14713(13) -0.0828(7) -0.0791(3) 0.0384(8) Uani 1 1 d . . . C11 C 0.10850(13) 0.0384(7) -0.1647(3) 0.0437(8) Uani 1 1 d . . . C12 C 0.12620(15) 0.2428(7) -0.2425(3) 0.0523(10) Uani 1 1 d . . . H12 H 0.1005 0.3256 -0.2978 0.063 Uiso 1 1 calc R . . C13 C 0.18098(16) 0.3166(8) -0.2357(3) 0.0540(10) Uani 1 1 d . . . H13 H 0.1927 0.4527 -0.2863 0.065 Uiso 1 1 calc R . . C14 C 0.22007(14) 0.1917(7) -0.1539(3) 0.0507(10) Uani 1 1 d . . . H14 H 0.2576 0.2424 -0.1520 0.061 Uiso 1 1 calc R . . C15 C 0.20427(13) -0.0031(7) -0.0769(3) 0.0422(8) Uani 1 1 d . . . C16 C 0.28134(13) 0.0154(8) 0.0773(3) 0.0429(8) Uani 1 1 d . . . O1 O 0.28339(9) 0.2843(5) 0.07760(19) 0.0569(7) Uani 1 1 d . . . N1 N 0.03251(12) -0.2326(7) -0.0981(3) 0.0657(10) Uani 1 1 d . . . N2 N 0.31501(12) -0.1516(7) 0.1501(3) 0.0538(9) Uani 1 1 d . . . N3 N 0.24389(11) -0.1360(7) 0.0058(2) 0.0455(8) Uani 1 1 d . . . H2N H 0.3090(14) -0.334(8) 0.152(3) 0.067(13) Uiso 1 1 d . . . H3N H 0.2433(14) -0.331(8) 0.013(3) 0.074(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.049(2) 0.052(2) 0.075(3) 0.006(2) 0.002(2) -0.009(2) C2 0.0407(19) 0.0311(19) 0.057(3) -0.0059(18) -0.0027(17) 0.0045(18) C3 0.055(2) 0.059(3) 0.058(3) 0.003(2) 0.002(2) -0.004(2) C4 0.084(3) 0.081(3) 0.057(3) -0.008(2) -0.010(2) 0.003(3) C5 0.068(3) 0.068(3) 0.091(4) -0.016(3) -0.023(3) 0.008(3) C6 0.045(2) 0.059(3) 0.114(4) 0.002(3) -0.006(2) -0.013(2) C7 0.053(2) 0.061(3) 0.064(3) 0.001(2) -0.0120(19) 0.002(2) C8 0.056(2) 0.071(3) 0.055(3) 0.005(2) -0.0021(19) -0.015(2) C9 0.050(2) 0.050(2) 0.046(2) 0.0019(18) -0.0062(17) -0.0046(19) C10 0.0445(19) 0.030(2) 0.039(2) -0.0047(16) -0.0010(16) -0.0031(17) C11 0.048(2) 0.039(2) 0.043(2) -0.0023(18) -0.0031(17) -0.0010(19) C12 0.064(3) 0.048(2) 0.042(2) 0.0023(18) -0.0073(18) 0.007(2) C13 0.066(3) 0.046(2) 0.050(3) 0.0079(19) 0.010(2) -0.001(2) C14 0.047(2) 0.044(2) 0.062(3) 0.000(2) 0.0100(19) -0.0068(19) C15 0.045(2) 0.0313(19) 0.049(2) -0.0040(17) -0.0008(17) 0.0012(18) C16 0.0396(19) 0.032(2) 0.057(2) -0.0018(19) 0.0018(17) -0.0021(19) O1 0.0630(15) 0.0252(14) 0.0780(19) -0.0009(13) -0.0122(13) -0.0019(12) N1 0.0526(19) 0.074(3) 0.068(3) 0.0032(19) -0.0026(18) -0.0116(18) N2 0.0558(19) 0.0249(17) 0.074(2) 0.0036(17) -0.0215(16) -0.0006(17) N3 0.0419(17) 0.0260(18) 0.065(2) -0.0024(16) -0.0088(14) -0.0013(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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(5) . ? C1 C2 1.377(4) . ? C2 C3 1.371(4) . ? C2 N2 1.419(4) . ? C3 C4 1.375(5) . ? C4 C5 1.357(5) . ? C5 C6 1.363(5) . ? C7 N1 1.309(4) . ? C7 C11 1.412(4) . ? C8 C9 1.355(4) . ? C8 N1 1.359(4) . ? C9 C10 1.402(4) . ? C10 C11 1.409(4) . ? C10 C15 1.418(4) . ? C11 C12 1.412(4) . ? C12 C13 1.353(4) . ? C13 C14 1.394(4) . ? C14 C15 1.361(4) . ? C15 N3 1.423(4) . ? C16 O1 1.235(3) . ? C16 N2 1.352(4) . ? C16 N3 1.355(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.5(4) . . ? C3 C2 C1 119.1(3) . . ? C3 C2 N2 119.6(3) . . ? C1 C2 N2 121.3(4) . . ? C2 C3 C4 121.2(4) . . ? C5 C4 C3 119.1(4) . . ? C4 C5 C6 120.7(4) . . ? C5 C6 C1 120.3(4) . . ? N1 C7 C11 124.9(3) . . ? C9 C8 N1 123.9(4) . . ? C8 C9 C10 120.4(3) . . ? C9 C10 C11 116.7(3) . . ? C9 C10 C15 125.3(3) . . ? C11 C10 C15 118.0(3) . . ? C10 C11 C7 117.8(3) . . ? C10 C11 C12 120.6(3) . . ? C7 C11 C12 121.7(3) . . ? C13 C12 C11 119.3(3) . . ? C12 C13 C14 120.9(3) . . ? C15 C14 C13 121.2(3) . . ? C14 C15 C10 119.9(3) . . ? C14 C15 N3 121.8(3) . . ? C10 C15 N3 118.3(3) . . ? O1 C16 N2 122.9(3) . . ? O1 C16 N3 122.5(3) . . ? N2 C16 N3 114.5(3) . . ? C7 N1 C8 116.4(3) . . ? C16 N2 C2 124.8(3) . . ? C16 N3 C15 123.7(3) . . ? _diffrn_measured_fraction_theta_max 0.765 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.173 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 949687' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_PQ6U _chemical_name_systematic ; 1-phenyl-3-(quinolin-6-yl)urea ; _chemical_name_common 'quinolinil based ligand' _chemical_formula_moiety C16H13ON3' _chemical_formula_sum C16H13ON3' _chemical_formula_weight 263.29 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 19.5009(3) _cell_length_b 4.6309(7) _cell_length_c 14.8429(9) _cell_angle_alpha 90 _cell_angle_beta 99.0647(7) _cell_angle_gamma 90 _cell_volume 1323.70(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293.15 _exptl_crystal_colour 'white powder' _cell_special_details ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.686 _exptl_special_details ? _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a1 and K\a2' _diffrn_radiation_wavelength 1.54056 _diffrn_radiation_monochromator none _refine_special_details ; Panalytical X'pert in bragg-brentano geometry ; _computing_data_collection "EXPO2010 (Altomare, 2010)'" _computing_cell_refinement 'TOPAS (Coelho ,2007)' _computing_structure_solution 'EXPO2010 (Altomare, 2010)' _computing_structure_refinement 'TOPAS (Coelho ,2007)' _pd_proc_2theta_range_min 3 _pd_proc_2theta_range_max 60 _pd_proc_info_excluded_regions no _pd_proc_ls_background_function Chebyschev _pd_proc_ls_pref_orient_corr ; Spherical Harmonics ; _refine_ls_structure_factor_coef Fsqd _pd_proc_ls_prof_R_factor 0.05025 _pd_proc_ls_prof_wR_factor 0.0944 _pd_proc_ls_prof_wR_expected 0.03505 _refine_ls_number_parameters 34 _refine_ls_goodness_of_fit_all 2.69 _refine_ls_number_restraints 4 _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr _pd_spec_mount_mode reflection _pd_spec_mounting ; flat stage ; _pd_spec_shape cylinder loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv C1z C 0 0.3247732 0.2431797 0.4597891 1 8.82(37) C2z C 0 0.3752701 0.03813861 0.4933121 1 8.82(37) C3z C 0 0.4182295 -0.07760922 0.4361042 1 8.82(37) C4z C 0 0.4110239 0.009045115 0.3455775 1 8.82(37) C5z C 0 0.3602037 0.2140535 0.3116542 1 8.82(37) C6z C 0 0.3173233 0.330698 0.3693568 1 8.82(37) N7z N 0 0.3503239 0.3090447 0.2243959 1 8.82(37) C8z C 0 0.3579868 0.1423511 0.1436224 1 8.82(37) N9z N 0 0.35306 0.30027 0.05809 1 8.82(37) O10z O 0 0.3685133 -0.1247186 0.1452883 1 8.82(37) C11z C 0 0.358367 0.1681953 -0.0298192 1 8.82(37) C12z C 0 0.3110993 0.247862 -0.1083498 1 8.82(37) C13z C 0 0.3165511 0.1265685 -0.1928691 1 8.82(37) C14z C 0 0.3694364 -0.07478548 -0.2007286 1 8.82(37) C15z C 0 0.4183029 -0.1456775 -0.1236054 1 8.82(37) C16z C 0 0.4126092 -0.02198941 -0.03780823 1 8.82(37) N17z N 0 0.3750053 -0.1959758 -0.2858719 1 8.82(37) C18z C 0 0.4253934 -0.3850823 -0.2910736 1 8.82(37) C19z C 0 0.4765233 -0.456387 -0.2160642 1 8.82(37) C20z C 0 0.4725617 -0.3407275 -0.1328281 1 8.82(37) H1z H 0 0.2913224 0.3339787 0.5047961 1 10.59(44) H2z H 0 0.3808746 -0.03063909 0.5642542 1 10.59(44) H3z H 0 0.4575492 -0.2363401 0.4623511 1 10.59(44) H4z H 0 0.4446915 -0.08160815 0.3008268 1 10.59(44) H5z H 0 0.2780895 0.4901324 0.3434189 1 10.59(44) H6z H 0 0.3360594 0.5187826 0.2142646 1 10.59(44) H7z H 0 0.3454167 0.5168914 0.05967358 1 10.59(44) H8z H 0 0.2703423 0.4044754 -0.1026743 1 10.59(44) H9z H 0 0.2798588 0.1875673 -0.2529467 1 10.59(44) H10z H 0 0.4505267 -0.07525304 0.02187334 1 10.59(44) H11z H 0 0.4294151 -0.4792585 -0.3572656 1 10.59(44) H12z H 0 0.517838 -0.6075946 -0.2243667 1 10.59(44) H13z H 0 0.5107908 -0.3977419 -0.07386287 1 10.59(44) _vrf_GEOM001_I ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM003_I ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM006_I ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM007_I ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bonds and angles not calculated. ; _database_code_depnum_ccdc_archive 'CCDC 949688' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_s2-w_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 N6 O' _chemical_formula_weight 343.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1275(13) _cell_length_b 10.2052(9) _cell_length_c 16.4320(17) _cell_angle_alpha 90.00 _cell_angle_beta 105.398(11) _cell_angle_gamma 90.00 _cell_volume 1799.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2364 _cell_measurement_theta_min 2.7548 _cell_measurement_theta_max 28.7891 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90479 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7850 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_unetI/netI 0.0914 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.90 _reflns_number_total 4037 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 32.00 91.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.2205 38.0000 -180.0000 59 #__ type_ start__ end____ width___ exp.time_ 2 omega -39.00 77.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 18.2205 0.0000 -30.0000 116 #__ type_ start__ end____ width___ exp.time_ 3 omega -82.00 -34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -18.6892 179.0000 -120.0000 48 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_structure_solution 'SHELXs-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4037 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1313 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.895 _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 N1 N 0.22596(16) 0.56792(17) 0.25531(11) 0.0394(5) Uani 1 1 d . . . H1N H 0.2563(18) 0.6461(19) 0.2614(11) 0.036(6) Uiso 1 1 d . . . N2 N 0.39031(15) 0.53592(16) 0.20126(10) 0.0312(4) Uani 1 1 d . . . H2N H 0.3801(18) 0.6184(19) 0.1805(11) 0.049(7) Uiso 1 1 d . . . N3 N 0.46899(15) 0.45169(14) 0.17458(9) 0.0304(4) Uani 1 1 d . . . N4 N 0.26265(19) 0.48906(18) 0.02468(11) 0.0596(6) Uani 1 1 d . . . N5 N 0.55025(16) 0.31231(16) 0.10353(10) 0.0392(4) Uani 1 1 d . . . N6 N 0.62075(15) 0.31024(15) 0.18696(10) 0.0375(4) Uani 1 1 d . . . N7 N 0.64220(15) 0.30719(16) 0.36624(10) 0.0395(4) Uani 1 1 d . . . O1 O 0.28525(14) 0.35843(13) 0.23096(9) 0.0531(4) Uani 1 1 d . . . C1 C 0.13113(17) 0.5458(2) 0.29591(11) 0.0360(5) Uani 1 1 d . . . C2 C 0.0904(2) 0.4226(2) 0.31092(14) 0.0554(6) Uani 1 1 d . . . H2 H 0.1235 0.3482 0.2923 0.066 Uiso 1 1 calc R . . C3 C -0.0003(3) 0.4113(3) 0.35394(17) 0.0753(8) Uani 1 1 d . . . H3 H -0.0270 0.3283 0.3647 0.090 Uiso 1 1 calc R . . C4 C -0.0513(3) 0.5184(3) 0.38095(17) 0.0785(9) Uani 1 1 d . . . H4 H -0.1115 0.5089 0.4105 0.094 Uiso 1 1 calc R . . C5 C -0.0134(2) 0.6392(3) 0.36423(16) 0.0724(8) Uani 1 1 d . . . H5 H -0.0495 0.7130 0.3811 0.087 Uiso 1 1 calc R . . C6 C 0.0783(2) 0.6542(2) 0.32238(13) 0.0526(6) Uani 1 1 d . . . H6 H 0.1044 0.7376 0.3121 0.063 Uiso 1 1 calc R . . C7 C 0.29612(18) 0.47668(19) 0.22894(11) 0.0332(5) Uani 1 1 d . . . C8 C 0.57010(18) 0.39380(17) 0.22836(11) 0.0301(5) Uani 1 1 d . . . C9 C 0.4586(2) 0.39518(18) 0.09747(12) 0.0345(5) Uani 1 1 d . . . C10 C 0.3605(2) 0.41778(19) 0.01920(12) 0.0394(5) Uani 1 1 d . . . C11 C 0.3716(2) 0.3625(2) -0.05535(12) 0.0493(6) Uani 1 1 d . . . H11 H 0.4418 0.3137 -0.0563 0.059 Uiso 1 1 calc R . . C12 C 0.2780(3) 0.3804(2) -0.12782(15) 0.0660(8) Uani 1 1 d . . . H12 H 0.2833 0.3441 -0.1787 0.079 Uiso 1 1 calc R . . C13 C 0.1769(3) 0.4528(3) -0.12351(16) 0.0765(9) Uani 1 1 d . . . H13 H 0.1118 0.4666 -0.1716 0.092 Uiso 1 1 calc R . . C14 C 0.1721(3) 0.5053(3) -0.04718(17) 0.0794(9) Uani 1 1 d . . . H14 H 0.1025 0.5545 -0.0453 0.095 Uiso 1 1 calc R . . C15 C 0.60935(17) 0.41616(19) 0.32023(11) 0.0308(5) Uani 1 1 d . . . C16 C 0.6112(2) 0.5381(2) 0.35499(13) 0.0502(6) Uani 1 1 d . . . H16 H 0.5901 0.6119 0.3210 0.060 Uiso 1 1 calc R . . C17 C 0.6453(2) 0.5489(2) 0.44197(15) 0.0658(8) Uani 1 1 d . . . H17 H 0.6465 0.6303 0.4675 0.079 Uiso 1 1 calc R . . C18 C 0.6771(2) 0.4398(2) 0.48958(14) 0.0601(7) Uani 1 1 d . . . H18 H 0.6993 0.4449 0.5482 0.072 Uiso 1 1 calc R . . C19 C 0.6759(2) 0.3222(2) 0.45009(13) 0.0529(6) Uani 1 1 d . . . H19 H 0.6999 0.2481 0.4834 0.063 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 N1 0.0371(11) 0.0299(10) 0.0555(12) -0.0025(9) 0.0197(9) -0.0023(9) N2 0.0361(10) 0.0266(9) 0.0325(9) 0.0031(8) 0.0120(8) 0.0051(8) N3 0.0369(9) 0.0292(9) 0.0259(9) 0.0006(8) 0.0099(8) 0.0033(8) N4 0.0597(14) 0.0610(13) 0.0456(12) -0.0040(10) -0.0078(10) 0.0119(11) N5 0.0533(11) 0.0336(9) 0.0333(10) -0.0016(8) 0.0161(9) 0.0023(9) N6 0.0460(11) 0.0335(10) 0.0342(10) -0.0005(8) 0.0125(8) 0.0053(8) N7 0.0458(11) 0.0364(10) 0.0321(10) 0.0039(8) 0.0029(8) -0.0012(8) O1 0.0625(11) 0.0292(8) 0.0760(11) -0.0011(8) 0.0335(9) -0.0041(8) C1 0.0267(11) 0.0466(13) 0.0334(11) -0.0002(10) 0.0057(9) -0.0022(11) C2 0.0471(15) 0.0525(15) 0.0730(17) 0.0033(13) 0.0273(13) -0.0050(12) C3 0.0616(19) 0.084(2) 0.089(2) 0.0111(17) 0.0356(17) -0.0149(16) C4 0.0547(18) 0.116(3) 0.077(2) 0.0023(19) 0.0383(15) -0.0031(19) C5 0.0581(18) 0.091(2) 0.0781(19) -0.0126(17) 0.0349(16) 0.0097(17) C6 0.0468(15) 0.0552(15) 0.0582(15) -0.0044(12) 0.0183(12) 0.0047(12) C7 0.0356(12) 0.0313(12) 0.0306(11) 0.0004(10) 0.0054(9) 0.0010(10) C8 0.0360(12) 0.0234(10) 0.0322(11) 0.0021(9) 0.0113(10) 0.0013(9) C9 0.0479(13) 0.0247(11) 0.0318(11) 0.0012(9) 0.0121(10) -0.0015(10) C10 0.0508(15) 0.0286(11) 0.0353(12) 0.0037(10) 0.0052(10) -0.0074(11) C11 0.0692(17) 0.0456(13) 0.0306(12) -0.0011(11) 0.0089(12) -0.0110(12) C12 0.095(2) 0.0580(17) 0.0391(15) -0.0028(13) 0.0076(15) -0.0265(17) C13 0.090(2) 0.070(2) 0.0473(16) 0.0018(15) -0.0216(15) -0.0175(17) C14 0.075(2) 0.0727(19) 0.072(2) -0.0053(16) -0.0114(16) 0.0143(16) C15 0.0277(11) 0.0325(11) 0.0313(11) -0.0001(10) 0.0063(9) 0.0029(9) C16 0.0608(15) 0.0389(13) 0.0418(13) -0.0037(11) -0.0024(11) 0.0162(11) C17 0.0774(19) 0.0565(16) 0.0486(15) -0.0188(13) -0.0093(13) 0.0250(14) C18 0.0715(18) 0.0669(17) 0.0314(12) -0.0079(13) -0.0044(12) 0.0146(14) C19 0.0629(16) 0.0515(14) 0.0362(13) 0.0068(12) -0.0011(12) 0.0013(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 N1 C7 1.358(2) . ? N1 C1 1.409(2) . ? N2 N3 1.379(2) . ? N2 C7 1.387(2) . ? N3 C8 1.367(2) . ? N3 C9 1.369(2) . ? N4 C10 1.332(3) . ? N4 C14 1.344(3) . ? N5 C9 1.308(2) . ? N5 N6 1.3872(19) . ? N6 C8 1.308(2) . ? N7 C19 1.337(2) . ? N7 C15 1.340(2) . ? O1 C7 1.214(2) . ? C1 C6 1.376(3) . ? C1 C2 1.380(3) . ? C2 C3 1.382(3) . ? C3 C4 1.360(4) . ? C4 C5 1.355(4) . ? C5 C6 1.382(3) . ? C8 C15 1.474(2) . ? C9 C10 1.467(3) . ? C10 C11 1.384(3) . ? C11 C12 1.370(3) . ? C12 C13 1.363(4) . ? C13 C14 1.378(3) . ? C15 C16 1.367(3) . ? C16 C17 1.382(3) . ? C17 C18 1.352(3) . ? C18 C19 1.363(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 127.42(18) . . ? N3 N2 C7 115.55(15) . . ? C8 N3 C9 105.62(16) . . ? C8 N3 N2 123.17(15) . . ? C9 N3 N2 130.70(16) . . ? C10 N4 C14 116.3(2) . . ? C9 N5 N6 108.06(15) . . ? C8 N6 N5 107.18(15) . . ? C19 N7 C15 116.51(17) . . ? C6 C1 C2 119.2(2) . . ? C6 C1 N1 117.21(19) . . ? C2 C1 N1 123.6(2) . . ? C1 C2 C3 119.1(2) . . ? C4 C3 C2 121.7(3) . . ? C3 C4 C5 119.1(3) . . ? C4 C5 C6 120.8(3) . . ? C1 C6 C5 120.2(2) . . ? O1 C7 N1 127.1(2) . . ? O1 C7 N2 122.11(18) . . ? N1 C7 N2 110.75(17) . . ? N6 C8 N3 109.87(16) . . ? N6 C8 C15 125.61(17) . . ? N3 C8 C15 124.37(17) . . ? N5 C9 N3 109.22(17) . . ? N5 C9 C10 123.48(18) . . ? N3 C9 C10 127.28(19) . . ? N4 C10 C11 123.3(2) . . ? N4 C10 C9 117.23(19) . . ? C11 C10 C9 119.5(2) . . ? C12 C11 C10 119.3(2) . . ? C13 C12 C11 118.3(2) . . ? C12 C13 C14 119.3(3) . . ? N4 C14 C13 123.4(3) . . ? N7 C15 C16 123.25(18) . . ? N7 C15 C8 114.31(16) . . ? C16 C15 C8 122.44(18) . . ? C15 C16 C17 118.3(2) . . ? C18 C17 C16 119.4(2) . . ? C17 C18 C19 118.8(2) . . ? N7 C19 C18 123.8(2) . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.152 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 949689' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_s2w_cubetto_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 N7 O' _chemical_formula_weight 357.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.1197(4) _cell_length_b 8.0872(7) _cell_length_c 17.6755(13) _cell_angle_alpha 90.00 _cell_angle_beta 91.449(6) _cell_angle_gamma 90.00 _cell_volume 874.50(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1340 _cell_measurement_theta_min 2.7643 _cell_measurement_theta_max 28.5646 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.71386 _exptl_absorpt_correction_T_max 1.00000 _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) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_device '92mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4122 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_unetI/netI 0.1081 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.63 _reflns_number_total 2847 _reflns_number_gt 1501 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 9.00 54.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 38.0000 30.0000 45 #__ type_ start__ end____ width___ exp.time_ 2 omega 40.00 93.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 179.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 3 omega 12.00 42.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 18.0642 -38.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 4 omega -95.00 -34.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 179.0000 -30.0000 61 #__ type_ start__ end____ width___ exp.time_ 5 omega -72.00 -32.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - -18.5330 179.0000 90.0000 40 ; _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0203(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(2) _refine_ls_number_reflns 2847 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1258 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.907 _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 N1 N 0.1030(4) 0.5763(4) 0.18422(14) 0.0415(9) Uani 1 1 d . . . H1N H 0.205(4) 0.652(5) 0.2059(15) 0.042(10) Uiso 1 1 d . . . N2 N -0.0759(4) 0.6591(4) 0.28956(15) 0.0365(9) Uani 1 1 d . . . H2N H 0.051(4) 0.662(5) 0.3196(15) 0.052(11) Uiso 1 1 d . . . N3 N -0.2606(4) 0.6323(4) 0.33361(13) 0.0323(7) Uani 1 1 d . . . N4 N -0.5186(4) 0.5156(4) 0.39817(14) 0.0470(9) Uani 1 1 d . . . N5 N -0.6021(4) 0.6574(4) 0.36344(14) 0.0427(9) Uani 1 1 d . . . N6 N -0.6545(4) 0.8788(5) 0.23580(16) 0.0458(9) Uani 1 1 d . . . N7 N 0.0106(4) 0.3448(4) 0.36037(14) 0.0449(9) Uani 1 1 d . . . O1 O -0.2562(3) 0.5072(4) 0.19858(11) 0.0484(8) Uani 1 1 d . . . C1 C 0.3935(5) 0.5001(7) 0.0091(2) 0.0713(15) Uani 1 1 d . . . H1 H 0.5252 0.5307 -0.0120 0.086 Uiso 1 1 calc R . . C2 C 0.2503(6) 0.4008(7) -0.0302(2) 0.0804(17) Uani 1 1 d . . . H2 H 0.2838 0.3642 -0.0784 0.096 Uiso 1 1 calc R . . C3 C 0.0577(7) 0.3552(7) 0.0013(2) 0.0818(16) Uani 1 1 d . . . H3 H -0.0377 0.2853 -0.0252 0.098 Uiso 1 1 calc R . . C4 C 0.0038(6) 0.4121(6) 0.0719(2) 0.0647(14) Uani 1 1 d . . . H4 H -0.1291 0.3826 0.0924 0.078 Uiso 1 1 calc R . . C5 C 0.1453(5) 0.5117(5) 0.11191(17) 0.0398(10) Uani 1 1 d . . . C6 C 0.3417(5) 0.5548(5) 0.08043(17) 0.0506(13) Uani 1 1 d . . . H6 H 0.4399 0.6212 0.1075 0.061 Uiso 1 1 calc R . . C7 C -0.0877(5) 0.5724(5) 0.22135(17) 0.0337(10) Uani 1 1 d . . . C8 C -0.3153(5) 0.4986(6) 0.37727(17) 0.0366(9) Uani 1 1 d . . . C9 C -0.1763(5) 0.3572(6) 0.39688(16) 0.0352(10) Uani 1 1 d . . . C10 C -0.2420(5) 0.2456(5) 0.45029(19) 0.0465(12) Uani 1 1 d . . . H10 H -0.3730 0.2602 0.4750 0.056 Uiso 1 1 calc R . . C11 C -0.1104(6) 0.1118(6) 0.46658(19) 0.0606(13) Uani 1 1 d . . . H11 H -0.1520 0.0338 0.5021 0.073 Uiso 1 1 calc R . . C12 C 0.0836(5) 0.0948(6) 0.42970(19) 0.0553(12) Uani 1 1 d . . . H12 H 0.1759 0.0055 0.4394 0.066 Uiso 1 1 calc R . . C13 C 0.1369(6) 0.2151(5) 0.3776(2) 0.0468(11) Uani 1 1 d . . . H13 H 0.2689 0.2049 0.3531 0.056 Uiso 1 1 calc R . . C14 C -0.4449(5) 0.7252(5) 0.32469(18) 0.0325(9) Uani 1 1 d . . . C15 C -0.4674(5) 0.8730(5) 0.27668(17) 0.0350(10) Uani 1 1 d . . . C16 C -0.3117(6) 0.9927(6) 0.27314(19) 0.0502(11) Uani 1 1 d . . . H16 H -0.1807 0.9821 0.3005 0.060 Uiso 1 1 calc R . . C17 C -0.3501(7) 1.1295(6) 0.2287(2) 0.0626(13) Uani 1 1 d . . . H17 H -0.2470 1.2138 0.2266 0.075 Uiso 1 1 calc R . . C18 C -0.5405(7) 1.1402(6) 0.1878(2) 0.0636(13) Uani 1 1 d . . . H18 H -0.5711 1.2315 0.1574 0.076 Uiso 1 1 calc R . . C19 C -0.6849(6) 1.0132(7) 0.1929(2) 0.0597(12) Uani 1 1 d . . . H19 H -0.8144 1.0204 0.1644 0.072 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 N1 0.0342(17) 0.052(3) 0.0384(17) -0.0070(18) 0.0043(14) -0.0165(17) N2 0.0247(15) 0.052(3) 0.0330(16) -0.0003(17) 0.0019(13) -0.0107(17) N3 0.0282(14) 0.032(2) 0.0366(15) 0.0076(16) 0.0013(12) -0.0053(16) N4 0.0363(16) 0.054(3) 0.0506(17) 0.013(2) 0.0082(14) -0.0018(18) N5 0.0362(15) 0.043(3) 0.0494(18) 0.0118(18) 0.0076(13) -0.0015(18) N6 0.0391(16) 0.038(3) 0.060(2) 0.010(2) -0.0058(14) -0.0036(18) N7 0.0359(16) 0.047(3) 0.0523(18) 0.0043(19) 0.0038(14) -0.0027(18) O1 0.0383(13) 0.058(2) 0.0483(13) -0.0037(15) -0.0056(10) -0.0185(15) C1 0.052(2) 0.108(5) 0.054(3) -0.003(3) 0.0118(19) 0.009(3) C2 0.081(3) 0.105(5) 0.056(3) -0.024(3) 0.014(2) 0.014(3) C3 0.096(4) 0.076(4) 0.074(3) -0.032(3) 0.009(3) -0.022(3) C4 0.070(3) 0.061(4) 0.064(3) -0.016(3) 0.012(2) -0.019(3) C5 0.043(2) 0.042(3) 0.035(2) 0.004(2) -0.0018(15) 0.004(2) C6 0.041(2) 0.068(4) 0.043(2) -0.007(2) 0.0025(16) 0.000(2) C7 0.0374(19) 0.025(3) 0.039(2) 0.0083(18) -0.0008(16) -0.0008(18) C8 0.0354(18) 0.038(3) 0.0363(19) 0.004(2) 0.0047(15) -0.006(2) C9 0.0342(19) 0.041(3) 0.0304(18) 0.000(2) -0.0020(15) -0.002(2) C10 0.045(2) 0.050(3) 0.045(2) 0.010(2) 0.0097(18) 0.006(2) C11 0.067(2) 0.063(4) 0.052(3) 0.024(3) 0.004(2) -0.001(3) C12 0.054(2) 0.051(4) 0.061(2) 0.013(2) -0.0041(19) 0.012(2) C13 0.037(2) 0.045(3) 0.058(2) 0.003(2) 0.0024(18) 0.005(2) C14 0.0312(19) 0.023(3) 0.043(2) 0.0000(18) 0.0029(16) -0.0067(19) C15 0.0336(19) 0.029(3) 0.042(2) 0.000(2) 0.0052(16) -0.005(2) C16 0.052(2) 0.045(3) 0.053(2) 0.010(2) -0.0082(17) -0.003(3) C17 0.071(3) 0.045(4) 0.071(3) 0.003(3) 0.003(2) -0.018(3) C18 0.078(3) 0.042(4) 0.072(3) 0.021(3) 0.006(2) 0.009(3) C19 0.057(2) 0.054(4) 0.067(3) 0.013(3) -0.011(2) 0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.354(4) . ? N1 C5 1.411(4) . ? N2 C7 1.395(4) . ? N2 N3 1.406(3) . ? N3 C14 1.361(4) . ? N3 C8 1.374(5) . ? N4 C8 1.314(4) . ? N4 N5 1.392(4) . ? N5 C14 1.314(4) . ? N6 C15 1.339(3) . ? N6 C19 1.335(5) . ? N7 C9 1.331(3) . ? N7 C13 1.334(5) . ? O1 C7 1.217(3) . ? C1 C2 1.366(5) . ? C1 C6 1.380(4) . ? C2 C3 1.367(5) . ? C3 C4 1.379(5) . ? C4 C5 1.367(5) . ? C5 C6 1.382(4) . ? C8 C9 1.462(5) . ? C9 C10 1.373(5) . ? C10 C11 1.375(5) . ? C11 C12 1.376(4) . ? C12 C13 1.384(5) . ? C14 C15 1.470(5) . ? C15 C16 1.361(5) . ? C16 C17 1.373(6) . ? C17 C18 1.358(4) . ? C18 C19 1.360(6) . ? 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 C7 N1 C5 127.7(3) . . ? C7 N2 N3 112.1(3) . . ? C14 N3 C8 106.7(2) . . ? C14 N3 N2 121.7(3) . . ? C8 N3 N2 130.0(3) . . ? C8 N4 N5 107.6(3) . . ? C14 N5 N4 107.9(3) . . ? C15 N6 C19 116.1(4) . . ? C9 N7 C13 116.7(3) . . ? C2 C1 C6 119.6(4) . . ? C1 C2 C3 120.0(4) . . ? C2 C3 C4 120.5(4) . . ? C5 C4 C3 120.2(4) . . ? C4 C5 C6 119.1(3) . . ? C4 C5 N1 123.9(3) . . ? C6 C5 N1 117.0(3) . . ? C1 C6 C5 120.6(4) . . ? O1 C7 N1 125.7(3) . . ? O1 C7 N2 121.9(3) . . ? N1 C7 N2 112.4(3) . . ? N4 C8 N3 108.7(4) . . ? N4 C8 C9 124.4(4) . . ? N3 C8 C9 126.9(3) . . ? N7 C9 C10 123.6(4) . . ? N7 C9 C8 116.5(3) . . ? C10 C9 C8 119.9(3) . . ? C11 C10 C9 118.7(3) . . ? C10 C11 C12 119.2(4) . . ? C11 C12 C13 117.7(4) . . ? N7 C13 C12 124.0(3) . . ? N5 C14 N3 108.9(3) . . ? N5 C14 C15 125.5(3) . . ? N3 C14 C15 125.5(3) . . ? N6 C15 C16 122.7(4) . . ? N6 C15 C14 114.0(3) . . ? C16 C15 C14 123.3(3) . . ? C15 C16 C17 119.3(4) . . ? C16 C17 C18 119.2(5) . . ? C19 C18 C17 117.8(5) . . ? N6 C19 C18 124.8(3) . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.143 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 949690'