# Electronic Supplementary Material (ESI) for CrystEngComm # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C22 H23 Ag N4 O4, F6 Sb' _chemical_formula_sum 'C22 H23 Ag F6 N4 O4 Sb' _chemical_formula_weight 751.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc ' 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 11.3040(2) _cell_length_b 19.5436(4) _cell_length_c 11.8709(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.3040(10) _cell_angle_gamma 90.00 _cell_volume 2620.41(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6525 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.22 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1468 _exptl_absorpt_coefficient_mu 1.857 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6539 _exptl_absorpt_correction_T_max 0.7681 _exptl_absorpt_process_details ' SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20288 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 30.39 _reflns_number_total 6903 _reflns_number_gt 4403 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.2000P] 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 0.0003(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6903 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1634 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Sb1 Sb 0.84016(3) 0.012043(18) 0.22033(3) 0.06703(16) Uani 1 1 d . . . Ag2 Ag 0.56040(3) 0.74346(2) 1.10905(3) 0.06070(15) Uani 1 1 d . . . O2 O -0.2230(3) 0.7281(2) 1.0173(3) 0.0667(9) Uani 1 1 d . . . O1 O 0.0925(3) 0.78773(18) 1.1741(3) 0.0615(8) Uani 1 1 d . . . C3 C 0.1448(4) 0.7240(2) 1.1538(4) 0.0531(10) Uani 1 1 d . . . H3 H 0.1111 0.6891 1.2025 0.064 Uiso 1 1 calc R . . C4 C -0.0467(4) 0.7685(2) 0.9344(4) 0.0529(10) Uani 1 1 d . . . H4 H -0.0604 0.7936 0.8636 0.064 Uiso 1 1 calc R . . O3 O 0.3722(6) 0.5059(2) 0.9316(4) 0.108(2) Uani 1 1 d . . . C6 C 0.2751(5) 0.7304(3) 1.1800(4) 0.0607(12) Uani 1 1 d . . . N1 N 0.6784(4) 0.7841(3) 1.2494(3) 0.0682(11) Uani 1 1 d . . . C8 C 0.1168(4) 0.7062(2) 1.0300(3) 0.0481(10) Uani 1 1 d . . . H8 H 0.1864 0.6872 0.9945 0.058 Uiso 1 1 calc R . . C9 C 0.0100(4) 0.6597(2) 1.0119(4) 0.0543(11) Uani 1 1 d . . . H9A H -0.0347 0.6572 1.0798 0.065 Uiso 1 1 calc R . . H9B H 0.0348 0.6139 0.9921 0.065 Uiso 1 1 calc R . . C10 C 0.6336(5) 0.9782(2) 0.8671(4) 0.0617(13) Uani 1 1 d . . . H10 H 0.6484 0.9710 0.9482 0.074 Uiso 1 1 calc R . . C11 C -0.1961(4) 0.6823(2) 0.9306(3) 0.0506(10) Uani 1 1 d . . . H11 H -0.2125 0.6353 0.9537 0.061 Uiso 1 1 calc R . . C12 C 0.7325(4) 0.8003(2) 1.3264(3) 0.0518(10) Uani 1 1 d . . . C13 C -0.0652(4) 0.6916(2) 0.9152(3) 0.0488(10) Uani 1 1 d . . . H13 H -0.0409 0.6766 0.8408 0.059 Uiso 1 1 calc R . . C14 C 0.0810(4) 0.7766(2) 0.9768(4) 0.0521(10) Uani 1 1 d . . . H14 H 0.1313 0.7869 0.9137 0.063 Uiso 1 1 calc R . . C15 C 0.5747(5) 1.0472(3) 0.8438(4) 0.0719(15) Uani 1 1 d . . . H15A H 0.4894 1.0420 0.8363 0.086 Uiso 1 1 calc R . . H15B H 0.5932 1.0789 0.9048 0.086 Uiso 1 1 calc R . . C16 C 0.1060(5) 0.8273(2) 1.0726(4) 0.0657(13) Uani 1 1 d . . . H16A H 0.1857 0.8455 1.0697 0.079 Uiso 1 1 calc R . . H16B H 0.0501 0.8650 1.0687 0.079 Uiso 1 1 calc R . . C17 C 0.6231(5) 1.0731(2) 0.7349(4) 0.0643(13) Uani 1 1 d . . . H17 H 0.6300 1.1230 0.7358 0.077 Uiso 1 1 calc R . . C18 C -0.1440(5) 0.7848(3) 1.0164(4) 0.0618(12) Uani 1 1 d . . . H18A H -0.1094 0.7926 1.0914 0.074 Uiso 1 1 calc R . . H18B H -0.1863 0.8259 0.9924 0.074 Uiso 1 1 calc R . . N3 N 0.3718(5) 0.7372(3) 1.1986(5) 0.0838(14) Uani 1 1 d . . . N2 N 0.5134(5) 0.6509(3) 0.9974(4) 0.0947(17) Uani 1 1 d . . . C28 C 0.5428(6) 0.8643(3) 0.8981(4) 0.0721(15) Uani 1 1 d . . . C21 C 0.4855(5) 0.6062(3) 0.9437(5) 0.0722(14) Uani 1 1 d . . . C24 C 0.7433(5) 1.0398(3) 0.7204(5) 0.0706(14) Uani 1 1 d . . . H24 H 0.8061 1.0728 0.7404 0.085 Uiso 1 1 calc R . . C22 C 0.4471(6) 0.5483(3) 0.8725(5) 0.0783(17) Uani 1 1 d . . . H22 H 0.5165 0.5222 0.8506 0.094 Uiso 1 1 calc R . . C25 C 0.7502(6) 0.9786(4) 0.8042(5) 0.094(2) Uani 1 1 d . . . H25 H 0.8187 0.9830 0.8570 0.112 Uiso 1 1 calc R . . C23 C 0.2545(8) 0.5247(3) 0.8982(5) 0.095(2) Uani 1 1 d . . . H23A H 0.2297 0.5645 0.9399 0.114 Uiso 1 1 calc R . . H23B H 0.2003 0.4874 0.9116 0.114 Uiso 1 1 calc R . . C27 C 0.5674(8) 0.9174(3) 0.8129(5) 0.102(3) Uani 1 1 d . . . F2 F 0.7786(6) 0.0761(3) 0.3220(5) 0.163(2) Uani 1 1 d . . . F5 F 0.9465(6) 0.0785(3) 0.1886(7) 0.206(3) Uani 1 1 d . . . F3 F 0.7328(6) -0.0487(3) 0.2729(9) 0.228(4) Uani 1 1 d . . . F1 F 0.7355(9) 0.0458(5) 0.1179(6) 0.237(4) Uani 1 1 d . . . F4 F 0.9011(10) -0.0476(4) 0.1300(10) 0.311(6) Uani 1 1 d . . . N4 N 0.5284(5) 0.8271(2) 0.9667(4) 0.0884(15) Uani 1 1 d . . . F6 F 0.9412(9) -0.0182(5) 0.3287(10) 0.280(6) Uani 1 1 d . . . C37 C 0.7393(11) 0.9028(6) 0.7558(9) 0.157(6) Uani 1 1 d . . . H37A H 0.7860 0.8979 0.6895 0.188 Uiso 1 1 calc R . . H37B H 0.7676 0.8701 0.8121 0.188 Uiso 1 1 calc R . . O4 O 0.6298(11) 0.8925(3) 0.7305(5) 0.200(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.0639(3) 0.0513(2) 0.0854(3) 0.00276(15) -0.00285(19) 0.00335(14) Ag2 0.0552(3) 0.0701(3) 0.0561(2) -0.00898(16) -0.00535(17) -0.01153(16) O2 0.057(2) 0.092(3) 0.0514(18) -0.0141(17) 0.0109(15) -0.0026(19) O1 0.059(2) 0.076(2) 0.0501(17) -0.0160(15) 0.0071(14) 0.0093(16) C3 0.051(3) 0.058(2) 0.050(2) 0.0018(19) -0.0004(19) -0.002(2) C4 0.065(3) 0.049(2) 0.045(2) 0.0094(18) 0.002(2) 0.008(2) O3 0.185(6) 0.051(2) 0.083(3) 0.0191(19) -0.053(3) -0.024(3) C6 0.051(3) 0.071(3) 0.059(3) 0.001(2) -0.002(2) -0.005(2) N1 0.061(3) 0.086(3) 0.056(2) -0.012(2) -0.0092(19) -0.013(2) C8 0.049(2) 0.051(2) 0.045(2) -0.0016(17) 0.0045(18) 0.0068(18) C9 0.056(3) 0.043(2) 0.062(3) 0.0018(18) -0.016(2) 0.0059(18) C10 0.085(4) 0.062(3) 0.037(2) -0.0010(19) -0.007(2) 0.001(2) C11 0.053(3) 0.058(2) 0.040(2) 0.0003(18) -0.0070(18) 0.002(2) C12 0.048(2) 0.060(3) 0.047(2) -0.0032(19) 0.0000(19) -0.0073(19) C13 0.052(2) 0.054(2) 0.0400(19) -0.0043(17) -0.0002(17) 0.0094(19) C14 0.059(3) 0.052(2) 0.046(2) 0.0079(18) 0.014(2) -0.003(2) C15 0.076(4) 0.071(3) 0.068(3) -0.026(3) -0.003(3) 0.016(3) C16 0.073(3) 0.048(2) 0.076(3) -0.005(2) 0.000(3) -0.001(2) C17 0.080(4) 0.045(2) 0.066(3) -0.007(2) -0.015(3) -0.007(2) C18 0.058(3) 0.057(3) 0.070(3) -0.012(2) 0.006(2) 0.012(2) N3 0.052(3) 0.111(4) 0.087(3) -0.009(3) -0.009(2) -0.008(3) N2 0.122(5) 0.063(3) 0.097(4) -0.014(3) -0.015(3) -0.011(3) C28 0.103(4) 0.056(3) 0.057(3) 0.006(2) -0.002(3) 0.011(3) C21 0.083(4) 0.060(3) 0.073(3) -0.008(3) -0.013(3) -0.003(3) C24 0.061(3) 0.075(3) 0.075(3) -0.012(3) 0.004(3) -0.026(3) C22 0.106(5) 0.057(3) 0.069(3) -0.020(2) -0.033(3) 0.021(3) C25 0.068(4) 0.142(6) 0.070(3) 0.012(4) -0.010(3) 0.038(4) C23 0.146(7) 0.068(4) 0.073(4) -0.006(3) 0.024(4) 0.006(4) C27 0.198(8) 0.058(3) 0.048(3) 0.003(2) -0.018(4) -0.015(4) F2 0.215(6) 0.133(4) 0.142(4) -0.038(3) 0.038(4) -0.010(4) F5 0.182(7) 0.122(4) 0.324(9) 0.011(5) 0.116(6) -0.038(4) F3 0.159(6) 0.107(4) 0.423(11) 0.016(6) 0.078(7) -0.055(4) F1 0.271(9) 0.264(9) 0.165(5) -0.007(6) -0.138(6) 0.053(8) F4 0.350(13) 0.169(6) 0.425(15) -0.132(8) 0.180(12) 0.059(8) N4 0.127(5) 0.063(3) 0.076(3) 0.011(2) 0.013(3) 0.013(3) F6 0.197(8) 0.283(10) 0.351(13) 0.181(10) -0.100(8) 0.025(7) C37 0.242(14) 0.132(9) 0.099(7) -0.003(6) 0.041(8) 0.135(10) O4 0.460(17) 0.077(4) 0.066(4) -0.006(3) 0.059(7) -0.040(7) _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 Sb1 F4 1.744(6) . ? Sb1 F6 1.787(6) . ? Sb1 F1 1.788(6) . ? Sb1 F5 1.819(5) . ? Sb1 F3 1.826(6) . ? Sb1 F2 1.890(5) . ? Ag2 N1 2.237(4) . ? Ag2 N2 2.292(5) . ? Ag2 N4 2.369(5) . ? Ag2 N3 2.423(6) . ? O2 C11 1.405(5) . ? O2 C18 1.424(6) . ? O1 C3 1.405(6) . ? O1 C16 1.445(6) . ? C3 C6 1.498(7) . ? C3 C8 1.531(6) . ? C3 H3 0.9800 . ? C4 C14 1.518(7) . ? C4 C18 1.531(7) . ? C4 C13 1.533(6) . ? C4 H4 0.9800 . ? O3 C22 1.394(9) . ? O3 C23 1.421(10) . ? C6 N3 1.115(7) . ? N1 C12 1.125(5) . ? C8 C9 1.519(6) . ? C8 C14 1.561(6) . ? C8 H8 0.9800 . ? C9 C13 1.534(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.524(7) . ? C10 C27 1.532(8) . ? C10 C25 1.541(9) . ? C10 H10 0.9800 . ? C11 C12 1.489(5) 4_475 ? C11 C13 1.509(6) . ? C11 H11 0.9800 . ? C12 C11 1.489(5) 4_676 ? C13 H13 0.9800 . ? C14 C16 1.527(6) . ? C14 H14 0.9800 . ? C15 C17 1.511(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C24 1.522(8) . ? C17 C22 1.552(6) 2_656 ? C17 H17 0.9800 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N2 C21 1.120(6) . ? C28 N4 1.107(6) . ? C28 C27 1.484(8) . ? C21 C22 1.467(7) . ? C24 C23 1.439(8) 2_656 ? C24 C25 1.556(9) . ? C24 H24 0.9800 . ? C22 C17 1.552(6) 2_646 ? C22 H22 0.9800 . ? C25 C37 1.592(13) . ? C25 H25 0.9800 . ? C23 C24 1.439(8) 2_646 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C27 O4 1.322(11) . ? C37 O4 1.278(14) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? 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 F4 Sb1 F6 88.0(6) . . ? F4 Sb1 F1 95.4(5) . . ? F6 Sb1 F1 176.6(5) . . ? F4 Sb1 F5 94.0(4) . . ? F6 Sb1 F5 88.7(4) . . ? F1 Sb1 F5 91.2(4) . . ? F4 Sb1 F3 93.4(5) . . ? F6 Sb1 F3 87.3(4) . . ? F1 Sb1 F3 92.4(5) . . ? F5 Sb1 F3 171.4(4) . . ? F4 Sb1 F2 178.0(5) . . ? F6 Sb1 F2 90.0(5) . . ? F1 Sb1 F2 86.6(4) . . ? F5 Sb1 F2 85.6(3) . . ? F3 Sb1 F2 86.9(3) . . ? N1 Ag2 N2 145.9(2) . . ? N1 Ag2 N4 110.85(19) . . ? N2 Ag2 N4 96.14(19) . . ? N1 Ag2 N3 101.51(17) . . ? N2 Ag2 N3 91.5(2) . . ? N4 Ag2 N3 103.6(2) . . ? C11 O2 C18 109.7(3) . . ? C3 O1 C16 105.8(3) . . ? O1 C3 C6 107.9(4) . . ? O1 C3 C8 107.1(3) . . ? C6 C3 C8 112.4(4) . . ? O1 C3 H3 109.8 . . ? C6 C3 H3 109.8 . . ? C8 C3 H3 109.8 . . ? C14 C4 C18 117.7(4) . . ? C14 C4 C13 105.9(3) . . ? C18 C4 C13 101.7(4) . . ? C14 C4 H4 110.4 . . ? C18 C4 H4 110.4 . . ? C13 C4 H4 110.4 . . ? C22 O3 C23 106.6(4) . . ? N3 C6 C3 177.8(6) . . ? C12 N1 Ag2 173.5(4) . . ? C9 C8 C3 113.8(4) . . ? C9 C8 C14 106.1(3) . . ? C3 C8 C14 103.2(3) . . ? C9 C8 H8 111.1 . . ? C3 C8 H8 111.1 . . ? C14 C8 H8 111.1 . . ? C8 C9 C13 106.1(3) . . ? C8 C9 H9A 110.5 . . ? C13 C9 H9A 110.5 . . ? C8 C9 H9B 110.5 . . ? C13 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C15 C10 C27 114.0(5) . . ? C15 C10 C25 106.5(5) . . ? C27 C10 C25 102.3(5) . . ? C15 C10 H10 111.2 . . ? C27 C10 H10 111.2 . . ? C25 C10 H10 111.2 . . ? O2 C11 C12 109.7(4) . 4_475 ? O2 C11 C13 104.7(3) . . ? C12 C11 C13 111.9(4) 4_475 . ? O2 C11 H11 110.1 . . ? C12 C11 H11 110.1 4_475 . ? C13 C11 H11 110.1 . . ? N1 C12 C11 176.8(5) . 4_676 ? C11 C13 C4 103.2(4) . . ? C11 C13 C9 112.1(4) . . ? C4 C13 C9 102.7(3) . . ? C11 C13 H13 112.7 . . ? C4 C13 H13 112.7 . . ? C9 C13 H13 112.7 . . ? C4 C14 C16 117.4(4) . . ? C4 C14 C8 105.7(4) . . ? C16 C14 C8 103.5(4) . . ? C4 C14 H14 109.9 . . ? C16 C14 H14 109.9 . . ? C8 C14 H14 109.9 . . ? C17 C15 C10 106.3(4) . . ? C17 C15 H15A 110.5 . . ? C10 C15 H15A 110.5 . . ? C17 C15 H15B 110.5 . . ? C10 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? O1 C16 C14 104.5(4) . . ? O1 C16 H16A 110.8 . . ? C14 C16 H16A 110.8 . . ? O1 C16 H16B 110.8 . . ? C14 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C15 C17 C24 108.1(4) . . ? C15 C17 C22 114.1(5) . 2_656 ? C24 C17 C22 101.7(4) . 2_656 ? C15 C17 H17 110.9 . . ? C24 C17 H17 110.9 . . ? C22 C17 H17 110.9 2_656 . ? O2 C18 C4 108.0(4) . . ? O2 C18 H18A 110.1 . . ? C4 C18 H18A 110.1 . . ? O2 C18 H18B 110.1 . . ? C4 C18 H18B 110.1 . . ? H18A C18 H18B 108.4 . . ? C6 N3 Ag2 142.4(5) . . ? C21 N2 Ag2 177.1(6) . . ? N4 C28 C27 175.5(6) . . ? N2 C21 C22 178.9(7) . . ? C23 C24 C17 104.4(5) 2_656 . ? C23 C24 C25 117.7(5) 2_656 . ? C17 C24 C25 106.1(4) . . ? C23 C24 H24 109.4 2_656 . ? C17 C24 H24 109.4 . . ? C25 C24 H24 109.4 . . ? O3 C22 C21 109.9(5) . . ? O3 C22 C17 107.3(5) . 2_646 ? C21 C22 C17 111.3(4) . 2_646 ? O3 C22 H22 109.4 . . ? C21 C22 H22 109.4 . . ? C17 C22 H22 109.4 2_646 . ? C10 C25 C24 107.0(5) . . ? C10 C25 C37 96.6(7) . . ? C24 C25 C37 118.9(6) . . ? C10 C25 H25 111.1 . . ? C24 C25 H25 111.1 . . ? C37 C25 H25 111.1 . . ? O3 C23 C24 105.9(6) . 2_646 ? O3 C23 H23A 110.6 . . ? C24 C23 H23A 110.6 2_646 . ? O3 C23 H23B 110.6 . . ? C24 C23 H23B 110.6 2_646 . ? H23A C23 H23B 108.7 . . ? O4 C27 C28 111.5(6) . . ? O4 C27 C10 109.3(8) . . ? C28 C27 C10 111.0(4) . . ? C28 N4 Ag2 162.6(6) . . ? O4 C37 C25 107.0(7) . . ? O4 C37 H37A 110.3 . . ? C25 C37 H37A 110.3 . . ? O4 C37 H37B 110.3 . . ? C25 C37 H37B 110.3 . . ? H37A C37 H37B 108.6 . . ? C37 O4 C27 107.9(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 O1 C3 C6 84.3(4) . . . . ? C16 O1 C3 C8 -37.0(5) . . . . ? O1 C3 C6 N3 -29(16) . . . . ? C8 C3 C6 N3 89(16) . . . . ? N2 Ag2 N1 C12 -67(4) . . . . ? N4 Ag2 N1 C12 153(4) . . . . ? N3 Ag2 N1 C12 43(4) . . . . ? O1 C3 C8 C9 -96.4(4) . . . . ? C6 C3 C8 C9 145.2(4) . . . . ? O1 C3 C8 C14 18.1(5) . . . . ? C6 C3 C8 C14 -100.3(4) . . . . ? C3 C8 C9 C13 133.2(4) . . . . ? C14 C8 C9 C13 20.4(4) . . . . ? C18 O2 C11 C12 -91.4(5) . . . 4_475 ? C18 O2 C11 C13 28.8(5) . . . . ? Ag2 N1 C12 C11 34(12) . . . 4_676 ? O2 C11 C13 C4 -36.3(4) . . . . ? C12 C11 C13 C4 82.4(4) 4_475 . . . ? O2 C11 C13 C9 73.4(4) . . . . ? C12 C11 C13 C9 -167.8(4) 4_475 . . . ? C14 C4 C13 C11 152.9(3) . . . . ? C18 C4 C13 C11 29.4(4) . . . . ? C14 C4 C13 C9 36.2(4) . . . . ? C18 C4 C13 C9 -87.3(4) . . . . ? C8 C9 C13 C11 -144.9(4) . . . . ? C8 C9 C13 C4 -34.8(4) . . . . ? C18 C4 C14 C16 -25.9(6) . . . . ? C13 C4 C14 C16 -138.7(4) . . . . ? C18 C4 C14 C8 88.9(4) . . . . ? C13 C4 C14 C8 -23.9(4) . . . . ? C9 C8 C14 C4 2.1(4) . . . . ? C3 C8 C14 C4 -117.9(4) . . . . ? C9 C8 C14 C16 126.1(4) . . . . ? C3 C8 C14 C16 6.2(5) . . . . ? C27 C10 C15 C17 -88.3(6) . . . . ? C25 C10 C15 C17 23.7(6) . . . . ? C3 O1 C16 C14 40.7(5) . . . . ? C4 C14 C16 O1 88.3(5) . . . . ? C8 C14 C16 O1 -27.7(5) . . . . ? C10 C15 C17 C24 -24.6(5) . . . . ? C10 C15 C17 C22 87.7(5) . . . 2_656 ? C11 O2 C18 C4 -9.5(5) . . . . ? C14 C4 C18 O2 -128.4(4) . . . . ? C13 C4 C18 O2 -13.3(5) . . . . ? C3 C6 N3 Ag2 -81(16) . . . . ? N1 Ag2 N3 C6 167.0(8) . . . . ? N2 Ag2 N3 C6 -44.7(8) . . . . ? N4 Ag2 N3 C6 51.9(8) . . . . ? N1 Ag2 N2 C21 134(10) . . . . ? N4 Ag2 N2 C21 -84(10) . . . . ? N3 Ag2 N2 C21 20(10) . . . . ? Ag2 N2 C21 C22 38(48) . . . . ? C15 C17 C24 C23 140.6(5) . . . 2_656 ? C22 C17 C24 C23 20.2(5) 2_656 . . 2_656 ? C15 C17 C24 C25 15.6(6) . . . . ? C22 C17 C24 C25 -104.8(5) 2_656 . . . ? C23 O3 C22 C21 97.4(5) . . . . ? C23 O3 C22 C17 -23.8(6) . . . 2_646 ? N2 C21 C22 O3 -90(41) . . . . ? N2 C21 C22 C17 29(42) . . . 2_646 ? C15 C10 C25 C24 -14.1(6) . . . . ? C27 C10 C25 C24 105.8(5) . . . . ? C15 C10 C25 C37 -137.1(5) . . . . ? C27 C10 C25 C37 -17.2(6) . . . . ? C23 C24 C25 C10 -117.1(7) 2_656 . . . ? C17 C24 C25 C10 -0.7(6) . . . . ? C23 C24 C25 C37 -9.3(10) 2_656 . . . ? C17 C24 C25 C37 107.1(7) . . . . ? C22 O3 C23 C24 37.9(6) . . . 2_646 ? N4 C28 C27 O4 118(9) . . . . ? N4 C28 C27 C10 -4(10) . . . . ? C15 C10 C27 O4 110.3(7) . . . . ? C25 C10 C27 O4 -4.2(7) . . . . ? C15 C10 C27 C28 -126.3(6) . . . . ? C25 C10 C27 C28 119.2(6) . . . . ? C27 C28 N4 Ag2 -68(10) . . . . ? N1 Ag2 N4 C28 63.4(16) . . . . ? N2 Ag2 N4 C28 -95.4(16) . . . . ? N3 Ag2 N4 C28 171.6(16) . . . . ? C10 C25 C37 O4 36.9(9) . . . . ? C24 C25 C37 O4 -76.6(11) . . . . ? C25 C37 O4 C27 -43.1(10) . . . . ? C28 C27 O4 C37 -92.8(9) . . . . ? C10 C27 O4 C37 30.3(10) . . . . ? _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.737 _refine_diff_density_min -0.714 _refine_diff_density_rms 0.090 _vrf_PLAT241_new ; PROBLEM: Check High Ueq as Compared to Neighbors for O4 RESPONSE: : This alarm is due to the elongated ADPs of Oxygen atom which suggest that these are probably disordered. In particular, the oxygen O4 in the five membered ring is disordered. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 942145' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 Ag N4 O4, F6 P' _chemical_formula_sum 'C22 H23 Ag F6 N4 O4 P' _chemical_formula_weight 660.28 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 11.2301(6) _cell_length_b 19.1920(11) _cell_length_c 11.8597(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.214(2) _cell_angle_gamma 90.00 _cell_volume 2554.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5891 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 25.67 _exptl_crystal_description Block _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1324 _exptl_absorpt_coefficient_mu 0.933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8354 _exptl_absorpt_correction_T_max 0.8963 _exptl_absorpt_process_details 'SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15074 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4169 _reflns_number_gt 3112 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0932P)^2^+8.2549P] 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 4169 _refine_ls_number_parameters 343 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1949 _refine_ls_wR_factor_gt 0.1737 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.44732(5) 0.74442(3) 0.38642(5) 0.0660(3) Uani 1 1 d . . . C1 C 0.5791(12) 0.4166(5) 0.8160(8) 0.158(7) Uani 1 1 d D . . H1 H 0.5084 0.4310 0.7709 0.189 Uiso 1 1 calc R . . C2 C 0.7790(13) 0.4136(8) 0.7845(17) 0.33(2) Uani 1 1 d D . . H2A H 0.8370 0.4104 0.7263 0.398 Uiso 1 1 calc R . . H2B H 0.8076 0.3874 0.8500 0.398 Uiso 1 1 calc R . . C3 C 0.7564(10) 0.4866(8) 0.8141(9) 0.133(5) Uani 1 1 d . . . C4 C 0.7458(8) 0.5416(5) 0.7244(8) 0.093(3) Uani 1 1 d . . . H4 H 0.8070 0.5772 0.7391 0.111 Uiso 1 1 calc R . . C5 C 0.7463(12) 0.5206(5) 0.6016(10) 0.110(4) Uani 1 1 d . . . H5A H 0.7693 0.5593 0.5547 0.132 Uiso 1 1 calc R . . H5B H 0.8005 0.4820 0.5907 0.132 Uiso 1 1 calc R . . C6 C 0.5574(10) 0.5481(5) 0.6274(8) 0.101(3) Uani 1 1 d . . . H6 H 0.4841 0.5246 0.6488 0.121 Uiso 1 1 calc R . . C7 C 0.6234(8) 0.5742(4) 0.7356(7) 0.078(2) Uani 1 1 d . . . H7 H 0.6288 0.6252 0.7358 0.093 Uiso 1 1 calc R . . C8 C 0.5750(8) 0.5483(4) 0.8430(7) 0.086(2) Uani 1 1 d . . . H8A H 0.4899 0.5399 0.8340 0.103 Uiso 1 1 calc R . . H8B H 0.5889 0.5820 0.9030 0.103 Uiso 1 1 calc R . . C9 C 0.6405(8) 0.4811(4) 0.8698(6) 0.078(2) Uani 1 1 d . . . H9 H 0.6527 0.4751 0.9514 0.093 Uiso 1 1 calc R . . C10 C 0.5246(9) 0.6063(5) 0.5497(8) 0.088(3) Uani 1 1 d . . . C11 C 0.7335(7) 0.7260(4) 0.3148(6) 0.0618(17) Uani 1 1 d . . . C12 C 0.8621(6) 0.7191(4) 0.3410(5) 0.0571(16) Uani 1 1 d . . . H12 H 0.8959 0.6833 0.2928 0.068 Uiso 1 1 calc R . . C13 C 0.8897(6) 0.7014(3) 0.4661(5) 0.0546(15) Uani 1 1 d . . . H13 H 0.8190 0.6827 0.5015 0.066 Uiso 1 1 calc R . . C14 C 0.9973(6) 0.6523(4) 0.4849(6) 0.0631(18) Uani 1 1 d . . . H14A H 0.9712 0.6059 0.5050 0.076 Uiso 1 1 calc R . . H14B H 1.0432 0.6493 0.4174 0.076 Uiso 1 1 calc R . . C15 C 1.0711(6) 0.6852(4) 0.5818(5) 0.0566(16) Uani 1 1 d . . . H15 H 1.0456 0.6703 0.6561 0.068 Uiso 1 1 calc R . . C16 C 1.2045(6) 0.6756(4) 0.5675(5) 0.0624(17) Uani 1 1 d . . . H16 H 1.2209 0.6276 0.5449 0.075 Uiso 1 1 calc R . . C17 C 1.1530(7) 0.7799(4) 0.4804(7) 0.071(2) Uani 1 1 d . . . H17A H 1.1187 0.7874 0.4050 0.086 Uiso 1 1 calc R . . H17B H 1.1951 0.8219 0.5041 0.086 Uiso 1 1 calc R . . C18 C 1.0547(6) 0.7638(3) 0.5617(6) 0.0586(17) Uani 1 1 d . . . H18 H 1.0681 0.7895 0.6325 0.070 Uiso 1 1 calc R . . C19 C 0.9263(6) 0.7721(3) 0.5182(6) 0.0580(16) Uani 1 1 d . . . H19 H 0.8752 0.7832 0.5809 0.070 Uiso 1 1 calc R . . C20 C 0.9049(7) 0.8241(4) 0.4228(7) 0.073(2) Uani 1 1 d . . . H20A H 0.8255 0.8437 0.4247 0.088 Uiso 1 1 calc R . . H20B H 0.9627 0.8616 0.4277 0.088 Uiso 1 1 calc R . . C21 C 0.4539(10) 0.8647(5) 0.6007(8) 0.091(3) Uani 1 1 d . . . C22 C 0.2757(6) 0.8068(4) 0.1721(6) 0.0599(17) Uani 1 1 d . . . F1 F 0.7482(11) 0.4601(6) 0.2658(16) 0.291(9) Uani 1 1 d . . . F2 F 0.7887(13) 0.5631(5) 0.3034(9) 0.236(6) Uani 1 1 d . . . F3 F 0.7445(14) 0.5393(9) 0.1376(10) 0.289(8) Uani 1 1 d . . . F4 F 0.9199(11) 0.5668(6) 0.1887(14) 0.271(7) Uani 1 1 d . . . F5 F 0.875(2) 0.4665(9) 0.1308(13) 0.367(11) Uani 1 1 d . . . F6 F 0.9238(11) 0.4778(9) 0.2884(17) 0.334(11) Uani 1 1 d . . . N1 N 0.4986(8) 0.6508(4) 0.4943(7) 0.103(3) Uani 1 1 d . . . N2 N 0.6359(7) 0.7351(4) 0.2965(7) 0.092(2) Uani 1 1 d . . . N3 N 0.4761(8) 0.8258(4) 0.5335(6) 0.094(2) Uani 1 1 d . . . N4 N 0.3310(6) 0.7903(4) 0.2486(5) 0.0750(17) Uani 1 1 d . . . O1 O 0.6659(15) 0.3889(5) 0.7446(9) 0.297(12) Uani 1 1 d D . . O2 O 0.6281(11) 0.5007(3) 0.5767(7) 0.147(4) Uani 1 1 d . . . O3 O 1.2341(5) 0.7219(3) 0.4801(4) 0.0751(14) Uani 1 1 d . . . O4 O 0.9186(5) 0.7839(3) 0.3222(4) 0.0730(14) Uani 1 1 d . . . P1 P 0.8337(2) 0.51057(13) 0.2174(2) 0.0902(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0611(4) 0.0758(4) 0.0606(4) 0.0083(3) -0.0065(3) 0.0095(3) C1 0.37(2) 0.056(5) 0.048(5) 0.003(5) -0.021(8) -0.018(8) C2 0.51(4) 0.29(3) 0.20(2) 0.090(19) 0.15(2) 0.36(3) C3 0.097(7) 0.216(15) 0.084(7) 0.018(8) -0.003(6) 0.073(9) C4 0.088(6) 0.089(6) 0.101(7) -0.018(5) 0.000(5) -0.034(5) C5 0.160(11) 0.061(5) 0.111(8) -0.013(5) 0.048(8) -0.017(6) C6 0.143(9) 0.066(5) 0.090(7) 0.017(5) -0.039(6) -0.026(6) C7 0.108(6) 0.043(4) 0.082(6) -0.004(4) -0.006(5) -0.003(4) C8 0.097(6) 0.068(5) 0.092(6) -0.031(5) 0.005(5) 0.010(4) C9 0.119(7) 0.072(5) 0.042(4) -0.011(4) 0.001(4) 0.003(5) C10 0.103(7) 0.068(5) 0.090(6) 0.010(5) -0.024(5) -0.013(5) C11 0.056(4) 0.069(4) 0.061(4) 0.002(3) -0.001(3) 0.004(3) C12 0.055(4) 0.068(4) 0.047(4) 0.001(3) 0.000(3) 0.007(3) C13 0.052(4) 0.062(4) 0.050(4) 0.005(3) 0.002(3) -0.012(3) C14 0.060(4) 0.057(4) 0.070(5) -0.002(3) -0.016(3) -0.007(3) C15 0.062(4) 0.063(4) 0.045(3) 0.001(3) 0.000(3) -0.008(3) C16 0.063(4) 0.075(4) 0.048(4) -0.009(3) -0.010(3) 0.000(3) C17 0.065(5) 0.074(5) 0.075(5) 0.005(4) -0.002(4) -0.021(4) C18 0.067(4) 0.058(4) 0.050(4) -0.015(3) 0.000(3) -0.009(3) C19 0.067(4) 0.056(4) 0.051(4) -0.006(3) 0.007(3) 0.000(3) C20 0.077(5) 0.059(4) 0.084(5) 0.006(4) -0.002(4) 0.000(4) C21 0.145(9) 0.060(5) 0.068(5) 0.001(4) -0.013(5) -0.009(5) C22 0.061(4) 0.066(4) 0.052(4) 0.000(3) -0.004(3) 0.006(3) F1 0.178(10) 0.138(8) 0.56(3) 0.035(12) 0.059(13) -0.046(7) F2 0.385(17) 0.153(8) 0.174(8) -0.041(7) 0.069(10) -0.022(10) F3 0.300(16) 0.358(18) 0.198(10) 0.007(12) -0.131(10) 0.106(14) F4 0.252(13) 0.146(8) 0.427(19) 0.034(10) 0.152(14) -0.030(8) F5 0.54(3) 0.308(18) 0.256(15) -0.151(14) 0.045(17) 0.17(2) F6 0.186(11) 0.335(18) 0.47(2) 0.249(18) -0.092(13) 0.025(10) N1 0.122(6) 0.071(5) 0.115(6) 0.026(5) -0.021(5) 0.005(4) N2 0.067(5) 0.114(6) 0.095(6) 0.013(4) -0.006(4) 0.007(4) N3 0.134(7) 0.074(4) 0.073(5) -0.007(4) 0.002(4) -0.009(4) N4 0.077(4) 0.089(5) 0.059(4) 0.012(3) -0.011(3) 0.014(3) O1 0.73(4) 0.068(5) 0.105(7) -0.028(5) 0.184(14) -0.026(11) O2 0.273(12) 0.051(3) 0.110(6) -0.021(4) -0.070(7) 0.015(5) O3 0.064(3) 0.108(4) 0.053(3) 0.011(3) 0.007(2) -0.002(3) O4 0.075(3) 0.088(4) 0.056(3) 0.023(3) 0.006(2) -0.015(3) P1 0.0933(17) 0.0705(14) 0.1053(19) -0.0055(13) -0.0155(14) 0.0034(12) _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 2.233(6) . ? Ag1 N1 2.267(8) . ? Ag1 N3 2.355(8) . ? Ag1 N2 2.414(8) . ? C1 O1 1.419(2) . ? C1 C21 1.460(14) 2_646 ? C1 C9 1.543(13) . ? C1 H1 0.9800 . ? C2 O1 1.419(2) . ? C2 C3 1.47(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C9 1.485(15) . ? C3 C4 1.500(16) . ? C4 C5 1.511(14) . ? C4 C7 1.520(13) . ? C4 H4 0.9800 . ? C5 O2 1.402(15) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.362(14) . ? C6 C10 1.485(12) . ? C6 C7 1.540(12) . ? C6 H6 0.9800 . ? C7 C8 1.490(11) . ? C7 H7 0.9800 . ? C8 C9 1.512(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9 0.9800 . ? C10 N1 1.110(10) . ? C11 N2 1.123(10) . ? C11 C12 1.472(10) . ? C12 O4 1.417(9) . ? C12 C13 1.542(9) . ? C12 H12 0.9800 . ? C13 C19 1.540(9) . ? C13 C14 1.542(9) . ? C13 H13 0.9800 . ? C14 C15 1.527(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.525(9) . ? C15 C18 1.536(9) . ? C15 H15 0.9800 . ? C16 O3 1.414(9) . ? C16 C22 1.489(9) 4_676 ? C16 H16 0.9800 . ? C17 O3 1.439(10) . ? C17 C18 1.526(10) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.521(10) . ? C18 H18 0.9800 . ? C19 C20 1.521(10) . ? C19 H19 0.9800 . ? C20 O4 1.433(9) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N3 1.127(11) . ? C21 C1 1.460(14) 2_656 ? C22 N4 1.125(8) . ? C22 C16 1.489(9) 4_475 ? F1 P1 1.494(11) . ? F2 P1 1.534(10) . ? F3 P1 1.459(10) . ? F4 P1 1.498(10) . ? F5 P1 1.421(10) . ? F6 P1 1.436(10) . ? 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 148.7(3) . . ? N4 Ag1 N3 109.9(3) . . ? N1 Ag1 N3 94.8(3) . . ? N4 Ag1 N2 101.8(3) . . ? N1 Ag1 N2 89.0(3) . . ? N3 Ag1 N2 106.2(3) . . ? O1 C1 C21 110.3(8) . 2_646 ? O1 C1 C9 103.9(8) . . ? C21 C1 C9 112.9(7) 2_646 . ? O1 C1 H1 109.9 . . ? C21 C1 H1 109.9 2_646 . ? C9 C1 H1 109.9 . . ? O1 C2 C3 103.8(9) . . ? O1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? O1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C2 C3 C9 101.6(13) . . ? C2 C3 C4 120.7(12) . . ? C9 C3 C4 108.6(8) . . ? C3 C4 C5 119.5(9) . . ? C3 C4 C7 105.9(8) . . ? C5 C4 C7 103.3(8) . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? C7 C4 H4 109.2 . . ? O2 C5 C4 103.7(8) . . ? O2 C5 H5A 111.0 . . ? C4 C5 H5A 111.0 . . ? O2 C5 H5B 111.0 . . ? C4 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? O2 C6 C10 111.3(9) . . ? O2 C6 C7 108.3(8) . . ? C10 C6 C7 111.9(7) . . ? O2 C6 H6 108.4 . . ? C10 C6 H6 108.4 . . ? C7 C6 H6 108.4 . . ? C8 C7 C4 107.4(7) . . ? C8 C7 C6 115.1(8) . . ? C4 C7 C6 101.6(7) . . ? C8 C7 H7 110.8 . . ? C4 C7 H7 110.8 . . ? C6 C7 H7 110.8 . . ? C7 C8 C9 105.8(7) . . ? C7 C8 H8A 110.6 . . ? C9 C8 H8A 110.6 . . ? C7 C8 H8B 110.6 . . ? C9 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? C3 C9 C8 105.9(8) . . ? C3 C9 C1 105.0(9) . . ? C8 C9 C1 113.0(8) . . ? C3 C9 H9 110.9 . . ? C8 C9 H9 110.9 . . ? C1 C9 H9 110.9 . . ? N1 C10 C6 177.9(12) . . ? N2 C11 C12 176.1(9) . . ? O4 C12 C11 109.2(6) . . ? O4 C12 C13 105.7(5) . . ? C11 C12 C13 112.5(6) . . ? O4 C12 H12 109.8 . . ? C11 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C19 C13 C12 103.5(5) . . ? C19 C13 C14 106.5(5) . . ? C12 C13 C14 113.7(6) . . ? C19 C13 H13 110.9 . . ? C12 C13 H13 110.9 . . ? C14 C13 H13 110.9 . . ? C15 C14 C13 104.8(5) . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14B 110.8 . . ? C13 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? C16 C15 C14 111.9(6) . . ? C16 C15 C18 102.3(5) . . ? C14 C15 C18 103.4(5) . . ? C16 C15 H15 112.8 . . ? C14 C15 H15 112.8 . . ? C18 C15 H15 112.8 . . ? O3 C16 C22 109.5(6) . 4_676 ? O3 C16 C15 105.4(6) . . ? C22 C16 C15 112.3(6) 4_676 . ? O3 C16 H16 109.8 . . ? C22 C16 H16 109.8 4_676 . ? C15 C16 H16 109.8 . . ? O3 C17 C18 108.5(6) . . ? O3 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O3 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? C19 C18 C17 117.6(6) . . ? C19 C18 C15 105.2(5) . . ? C17 C18 C15 102.3(6) . . ? C19 C18 H18 110.4 . . ? C17 C18 H18 110.4 . . ? C15 C18 H18 110.4 . . ? C18 C19 C20 116.2(6) . . ? C18 C19 C13 106.2(5) . . ? C20 C19 C13 104.3(6) . . ? C18 C19 H19 110.0 . . ? C20 C19 H19 110.0 . . ? C13 C19 H19 110.0 . . ? O4 C20 C19 104.4(6) . . ? O4 C20 H20A 110.9 . . ? C19 C20 H20A 110.9 . . ? O4 C20 H20B 110.9 . . ? C19 C20 H20B 110.9 . . ? H20A C20 H20B 108.9 . . ? N3 C21 C1 177.3(11) . 2_656 ? N4 C22 C16 176.3(8) . 4_475 ? C10 N1 Ag1 177.9(8) . . ? C11 N2 Ag1 142.4(7) . . ? C21 N3 Ag1 159.3(9) . . ? C22 N4 Ag1 172.0(6) . . ? C1 O1 C2 107.6(11) . . ? C6 O2 C5 106.8(7) . . ? C16 O3 C17 108.5(5) . . ? C12 O4 C20 106.1(5) . . ? F5 P1 F6 85.6(11) . . ? F5 P1 F3 89.3(10) . . ? F6 P1 F3 174.9(11) . . ? F5 P1 F1 97.0(11) . . ? F6 P1 F1 86.6(8) . . ? F3 P1 F1 93.3(9) . . ? F5 P1 F4 92.0(11) . . ? F6 P1 F4 90.1(8) . . ? F3 P1 F4 90.8(9) . . ? F1 P1 F4 170.1(9) . . ? F5 P1 F2 175.1(9) . . ? F6 P1 F2 98.1(11) . . ? F3 P1 F2 87.0(8) . . ? F1 P1 F2 86.4(7) . . ? F4 P1 F2 84.8(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C9 41.6(16) . . . . ? O1 C2 C3 C4 -78.4(18) . . . . ? C2 C3 C4 C5 6.0(16) . . . . ? C9 C3 C4 C5 -110.4(11) . . . . ? C2 C3 C4 C7 122.0(12) . . . . ? C9 C3 C4 C7 5.5(12) . . . . ? C3 C4 C5 O2 82.5(11) . . . . ? C7 C4 C5 O2 -34.7(9) . . . . ? C3 C4 C7 C8 10.7(10) . . . . ? C5 C4 C7 C8 137.2(7) . . . . ? C3 C4 C7 C6 -110.5(9) . . . . ? C5 C4 C7 C6 16.0(8) . . . . ? O2 C6 C7 C8 -107.6(9) . . . . ? C10 C6 C7 C8 129.4(9) . . . . ? O2 C6 C7 C4 8.1(9) . . . . ? C10 C6 C7 C4 -115.0(9) . . . . ? C4 C7 C8 C9 -22.5(9) . . . . ? C6 C7 C8 C9 89.8(9) . . . . ? C2 C3 C9 C8 -147.6(10) . . . . ? C4 C3 C9 C8 -19.3(12) . . . . ? C2 C3 C9 C1 -27.7(11) . . . . ? C4 C3 C9 C1 100.5(11) . . . . ? C7 C8 C9 C3 25.8(10) . . . . ? C7 C8 C9 C1 -88.7(9) . . . . ? O1 C1 C9 C3 4.5(10) . . . . ? C21 C1 C9 C3 124.0(10) 2_646 . . . ? O1 C1 C9 C8 119.5(9) . . . . ? C21 C1 C9 C8 -121.0(10) 2_646 . . . ? O2 C6 C10 N1 -171(29) . . . . ? C7 C6 C10 N1 -50(30) . . . . ? N2 C11 C12 O4 -30(13) . . . . ? N2 C11 C12 C13 87(13) . . . . ? O4 C12 C13 C19 18.7(7) . . . . ? C11 C12 C13 C19 -100.3(7) . . . . ? O4 C12 C13 C14 -96.4(6) . . . . ? C11 C12 C13 C14 144.5(6) . . . . ? C19 C13 C14 C15 20.5(7) . . . . ? C12 C13 C14 C15 133.8(6) . . . . ? C13 C14 C15 C16 -144.4(6) . . . . ? C13 C14 C15 C18 -35.1(7) . . . . ? C14 C15 C16 O3 73.5(7) . . . . ? C18 C15 C16 O3 -36.6(6) . . . . ? C14 C15 C16 C22 -167.3(6) . . . 4_676 ? C18 C15 C16 C22 82.6(7) . . . 4_676 ? O3 C17 C18 C19 -128.7(6) . . . . ? O3 C17 C18 C15 -14.2(7) . . . . ? C16 C15 C18 C19 153.2(5) . . . . ? C14 C15 C18 C19 36.8(7) . . . . ? C16 C15 C18 C17 29.8(6) . . . . ? C14 C15 C18 C17 -86.6(6) . . . . ? C17 C18 C19 C20 -26.4(9) . . . . ? C15 C18 C19 C20 -139.4(6) . . . . ? C17 C18 C19 C13 89.0(7) . . . . ? C15 C18 C19 C13 -24.0(7) . . . . ? C12 C13 C19 C18 -117.9(6) . . . . ? C14 C13 C19 C18 2.2(7) . . . . ? C12 C13 C19 C20 5.3(7) . . . . ? C14 C13 C19 C20 125.4(6) . . . . ? C18 C19 C20 O4 89.1(7) . . . . ? C13 C19 C20 O4 -27.4(7) . . . . ? C6 C10 N1 Ag1 36(50) . . . . ? N4 Ag1 N1 C10 -146(24) . . . . ? N3 Ag1 N1 C10 -4(25) . . . . ? N2 Ag1 N1 C10 103(25) . . . . ? C12 C11 N2 Ag1 -80(13) . . . . ? N4 Ag1 N2 C11 166.3(12) . . . . ? N1 Ag1 N2 C11 -43.4(12) . . . . ? N3 Ag1 N2 C11 51.3(12) . . . . ? C1 C21 N3 Ag1 -44(25) 2_656 . . . ? N4 Ag1 N3 C21 53(2) . . . . ? N1 Ag1 N3 C21 -108(2) . . . . ? N2 Ag1 N3 C21 162(2) . . . . ? C16 C22 N4 Ag1 6(16) 4_475 . . . ? N1 Ag1 N4 C22 -50(5) . . . . ? N3 Ag1 N4 C22 170(5) . . . . ? N2 Ag1 N4 C22 58(5) . . . . ? C21 C1 O1 C2 -99.3(14) 2_646 . . . ? C9 C1 O1 C2 21.9(14) . . . . ? C3 C2 O1 C1 -40.8(18) . . . . ? C10 C6 O2 C5 92.1(9) . . . . ? C7 C6 O2 C5 -31.3(10) . . . . ? C4 C5 O2 C6 41.5(10) . . . . ? C22 C16 O3 C17 -92.4(7) 4_676 . . . ? C15 C16 O3 C17 28.6(7) . . . . ? C18 C17 O3 C16 -8.8(8) . . . . ? C11 C12 O4 C20 83.7(6) . . . . ? C13 C12 O4 C20 -37.5(7) . . . . ? C19 C20 O4 C12 40.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.948 _refine_diff_density_min -0.714 _refine_diff_density_rms 0.095 _vrf_PLAT029_new ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.927 RESPONSE: Even though crystal data was collected up to 0.73 \%A resolution, the crystal (the largest available) still diffracted quite weakly at high angle. On repeated recrystallisation we could get only small sized crystals. ; _vrf_PLAT213_new ; PROBLEM: Atom C2 has ADP max/min Ratio ..... 6.1 prola RESPONSE: This alarm is due to the elongated ADPs of carbon atom C2 which suggest that these are probably disordered ; _vrf_PLAT234_new ; PROBLEM: Large Hirshfeld Difference O1 -- C2 .. 0.32 Ang. RESPONSE: This alarm is due to the elongated ADPs of carbon atom C2 which suggest that these are probably disordered ; _vrf_PLAT241_new ; PROBLEM: Check High Ueq as Compared to Neighbors for O1 RESPONSE: This alarm is due to the elongated ADPs of Oxygen atom O1 which suggest that these are probably disordered ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 942146' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C52 H55 Ag2 N8 O8, 2(F7 Sb)' _chemical_formula_sum 'C52 H55 Ag2 F14 N8 O8 Sb2' _chemical_formula_weight 1645.28 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' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall ' -P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.403(3) _cell_length_b 12.604(4) _cell_length_c 20.686(5) _cell_angle_alpha 89.498(15) _cell_angle_beta 89.662(15) _cell_angle_gamma 84.312(16) _cell_volume 2958.5(13) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6627 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 23.55 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1618 _exptl_absorpt_coefficient_mu 1.658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6819 _exptl_absorpt_correction_T_max 0.7890 _exptl_absorpt_process_details ' SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19280 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 0.98 _diffrn_reflns_theta_max 25.06 _reflns_number_total 10836 _reflns_number_gt 6469 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^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 10836 _refine_ls_number_parameters 775 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1956 _refine_ls_wR_factor_gt 0.1652 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.028 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 0.38421(5) 0.58570(5) 0.75421(3) 0.0579(2) Uani 1 1 d . . . Ag2 Ag 1.38400(5) 0.08580(5) 0.74562(3) 0.0584(2) Uani 1 1 d . . . C43 C 0.9601(6) 0.5077(6) 0.8376(3) 0.0496(19) Uani 1 1 d . . . H43A H 0.9513 0.4992 0.8839 0.059 Uiso 1 1 calc R . . H43B H 1.0041 0.5684 0.8291 0.059 Uiso 1 1 calc R . . C16 C 0.4139(7) 0.3654(6) 0.5149(3) 0.0488(19) Uani 1 1 d . . . H16 H 0.4868 0.3997 0.5195 0.059 Uiso 1 1 calc R . . C31 C 0.5867(7) 0.1342(6) 1.0150(3) 0.0478(18) Uani 1 1 d . . . H31 H 0.5136 0.1001 1.0203 0.057 Uiso 1 1 calc R . . C13 C -0.0160(6) 0.9127(6) 0.7628(4) 0.0486(18) Uani 1 1 d . . . H13 H -0.0198 0.8411 0.7811 0.058 Uiso 1 1 calc R . . C53 C 0.9835(7) 0.4132(6) 0.7368(4) 0.0498(18) Uani 1 1 d . . . H53 H 0.9801 0.3416 0.7193 0.060 Uiso 1 1 calc R . . O2 O 0.1691(4) 0.9857(4) 0.7455(3) 0.0556(14) Uani 1 1 d . . . C38 C 0.5609(6) 0.3255(6) 0.9807(4) 0.0498(18) Uani 1 1 d . . . H38 H 0.4890 0.3747 0.9842 0.060 Uiso 1 1 calc R . . O1 O -0.1593(4) 1.1661(4) 0.7669(3) 0.0562(14) Uani 1 1 d . . . O5 O 0.6988(5) 0.3572(5) 0.8982(3) 0.0729(16) Uani 1 1 d . . . O8 O 1.1692(4) 0.4853(4) 0.7544(3) 0.0577(14) Uani 1 1 d . . . C52 C 0.8591(6) 0.4749(6) 0.7375(3) 0.0467(18) Uani 1 1 d . . . H52 H 0.7994 0.4259 0.7292 0.056 Uiso 1 1 calc R . . O7 O 0.8409(4) 0.6652(4) 0.7329(3) 0.0548(13) Uani 1 1 d . . . O4 O 0.3005(5) 0.1442(5) 0.3969(3) 0.0746(17) Uani 1 1 d . . . C25 C 0.4285(6) 0.2488(7) 0.5414(4) 0.056(2) Uani 1 1 d . . . H25 H 0.5005 0.2376 0.5673 0.067 Uiso 1 1 calc R . . C30 C 0.6183(7) 0.1444(6) 0.9457(3) 0.055(2) Uani 1 1 d . . . H30A H 0.5946 0.0848 0.9212 0.066 Uiso 1 1 calc R . . H30B H 0.7025 0.1471 0.9404 0.066 Uiso 1 1 calc R . . C42 C 0.8405(6) 0.5231(6) 0.8052(3) 0.0467(18) Uani 1 1 d . . . H42 H 0.7824 0.4866 0.8298 0.056 Uiso 1 1 calc R . . C12 C -0.1404(6) 0.9748(6) 0.7635(4) 0.0467(18) Uani 1 1 d . . . H12 H -0.1999 0.9258 0.7731 0.056 Uiso 1 1 calc R . . O3 O 0.2468(5) 0.3378(5) 0.5742(3) 0.0736(17) Uani 1 1 d . . . C26 C 0.4393(6) 0.1742(7) 0.4821(4) 0.057(2) Uani 1 1 d . . . H26 H 0.5112 0.1251 0.4855 0.068 Uiso 1 1 calc R . . C41 C 0.7960(6) 0.6385(6) 0.7932(4) 0.0493(19) Uani 1 1 d . . . H41 H 0.8260 0.6833 0.8266 0.059 Uiso 1 1 calc R . . O6 O 0.7544(5) 0.1618(5) 1.0740(3) 0.0697(16) Uani 1 1 d . . . N8 N 1.2697(6) 0.2345(6) 0.7689(4) 0.0663(19) Uani 1 1 d . . . N1 N 0.2689(6) 0.7322(6) 0.7306(3) 0.0631(18) Uani 1 1 d . . . C3 C -0.1601(6) 1.0229(6) 0.6942(3) 0.0492(19) Uani 1 1 d . . . H3 H -0.2186 0.9869 0.6705 0.059 Uiso 1 1 calc R . . C39 C 0.5720(6) 0.2508(6) 1.0405(4) 0.0520(19) Uani 1 1 d . . . H39 H 0.4995 0.2616 1.0663 0.062 Uiso 1 1 calc R . . C2 C -0.2036(6) 1.1396(6) 0.7068(4) 0.0494(18) Uani 1 1 d . . . H2 H -0.1741 1.1850 0.6729 0.059 Uiso 1 1 calc R . . C7 C 0.2192(7) 0.8086(6) 0.7149(4) 0.0513(19) Uani 1 1 d . . . C18 C 0.4503(7) 0.2508(6) 0.4244(3) 0.0497(19) Uani 1 1 d . . . H18 H 0.5329 0.2602 0.4150 0.060 Uiso 1 1 calc R . . N6 N 1.5658(6) 0.1675(7) 0.7136(4) 0.083(2) Uani 1 1 d . . . C5 C 0.0220(6) 0.9050(5) 0.6931(3) 0.0463(18) Uani 1 1 d . . . H5 H 0.0014 0.8398 0.6724 0.056 Uiso 1 1 calc R . . C17 C 0.3813(7) 0.3569(6) 0.4448(3) 0.0527(19) Uani 1 1 d . . . H17A H 0.4056 0.4163 0.4197 0.063 Uiso 1 1 calc R . . H17B H 0.2971 0.3543 0.4399 0.063 Uiso 1 1 calc R . . C8 C 0.0866(6) 0.9673(6) 0.7954(3) 0.0517(19) Uani 1 1 d . . . H8 H 0.1254 0.9177 0.8271 0.062 Uiso 1 1 calc R . . C34 C 0.6792(8) 0.2571(7) 1.0849(4) 0.063(2) Uani 1 1 d . . . H34 H 0.6522 0.2575 1.1300 0.076 Uiso 1 1 calc R . . C46 C 1.2190(6) 0.3100(7) 0.7856(4) 0.055(2) Uani 1 1 d . . . C4 C -0.0402(6) 1.0067(7) 0.6623(3) 0.054(2) Uani 1 1 d . . . H4A H 0.0040 1.0672 0.6701 0.065 Uiso 1 1 calc R . . H4B H -0.0479 0.9981 0.6160 0.065 Uiso 1 1 calc R . . C19 C 0.3937(7) 0.1941(7) 0.3688(4) 0.062(2) Uani 1 1 d . . . C44 C 1.0232(6) 0.4062(6) 0.8078(4) 0.0488(18) Uani 1 1 d . . . H44 H 1.0031 0.3410 0.8296 0.059 Uiso 1 1 calc R . . N5 N 1.4516(8) -0.0479(7) 0.6796(4) 0.088(3) Uani 1 1 d . . . C6 C 0.1537(6) 0.9116(6) 0.6961(4) 0.0508(19) Uani 1 1 d . . . H6 H 0.1832 0.9369 0.6547 0.061 Uiso 1 1 calc R . . N4 N 0.5662(6) 0.6680(7) 0.7866(4) 0.088(3) Uani 1 1 d . . . C37 C 0.6662(8) 0.3881(7) 0.9643(4) 0.062(2) Uani 1 1 d . . . H37 H 0.6421 0.4649 0.9659 0.074 Uiso 1 1 calc R . . C32 C 0.6830(8) 0.0809(7) 1.0568(4) 0.066(2) Uani 1 1 d . . . H32 H 0.7299 0.0261 1.0317 0.079 Uiso 1 1 calc R . . C51 C 0.8389(6) 0.5741(7) 0.6927(3) 0.053(2) Uani 1 1 d . . . H51 H 0.7615 0.5752 0.6723 0.063 Uiso 1 1 calc R . . C9 C 0.0530(7) 1.0748(8) 0.8283(4) 0.073(3) Uani 1 1 d . . . H9A H 0.1103 1.0853 0.8615 0.088 Uiso 1 1 calc R . . H9B H 0.0554 1.1318 0.7966 0.088 Uiso 1 1 calc R . . C21 C 0.3344(8) 0.1113(7) 0.4657(4) 0.070(2) Uani 1 1 d . . . H21 H 0.3578 0.0344 0.4682 0.083 Uiso 1 1 calc R . . C48 C 1.0865(7) 0.4694(7) 0.7033(4) 0.057(2) Uani 1 1 d . . . H48 H 1.1256 0.4207 0.6715 0.068 Uiso 1 1 calc R . . C15 C 0.3169(8) 0.4188(7) 0.5558(4) 0.063(2) Uani 1 1 d . . . H15 H 0.2702 0.4737 0.5306 0.075 Uiso 1 1 calc R . . C24 C 0.3222(8) 0.2428(7) 0.5847(4) 0.062(2) Uani 1 1 d . . . H24 H 0.3478 0.2401 0.6299 0.075 Uiso 1 1 calc R . . C40 C 0.6652(7) 0.6556(6) 0.7916(4) 0.058(2) Uani 1 1 d . . . C29 C 0.5502(7) 0.2495(6) 0.9235(3) 0.053(2) Uani 1 1 d . . . H29 H 0.4677 0.2403 0.9142 0.063 Uiso 1 1 calc R . . C14 C 0.3676(9) 0.4673(8) 0.6138(5) 0.079(3) Uani 1 1 d . . . C28 C 0.6062(7) 0.3058(7) 0.8695(4) 0.059(2) Uani 1 1 d . . . H28 H 0.6378 0.2550 0.8366 0.071 Uiso 1 1 calc R . . N2 N 0.4093(9) 0.5035(7) 0.6562(4) 0.095(3) Uani 1 1 d . . . C10 C -0.0680(7) 1.0805(8) 0.8583(3) 0.069(3) Uani 1 1 d . . . H10A H -0.0837 1.1471 0.8813 0.082 Uiso 1 1 calc R . . H10B H -0.0714 1.0225 0.8891 0.082 Uiso 1 1 calc R . . C11 C -0.1608(6) 1.0733(7) 0.8067(4) 0.053(2) Uani 1 1 d . . . H11 H -0.2382 1.0739 0.8276 0.064 Uiso 1 1 calc R . . C49 C 1.0524(7) 0.5745(7) 0.6711(4) 0.064(2) Uani 1 1 d . . . H49A H 1.1098 0.5865 0.6377 0.076 Uiso 1 1 calc R . . H49B H 1.0537 0.6308 0.7027 0.076 Uiso 1 1 calc R . . C45 C 1.1539(6) 0.4133(6) 0.8039(4) 0.0520(19) Uani 1 1 d . . . H45 H 1.1834 0.4387 0.8448 0.062 Uiso 1 1 calc R . . C1 C -0.3355(7) 1.1554(6) 0.7092(4) 0.057(2) Uani 1 1 d . . . N3 N 0.4526(8) 0.4524(7) 0.8209(4) 0.088(3) Uani 1 1 d . . . C20 C 0.4815(9) 0.1103(8) 0.3410(4) 0.074(3) Uani 1 1 d . . . C27 C 0.5182(8) 0.3864(7) 0.8409(4) 0.064(2) Uani 1 1 d . . . C35 C 0.7497(11) 0.3524(9) 1.0738(5) 0.096(3) Uani 1 1 d . . . H35A H 0.7039 0.4171 1.0879 0.116 Uiso 1 1 calc R . . H35B H 0.8217 0.3433 1.0988 0.116 Uiso 1 1 calc R . . C50 C 0.9319(8) 0.5796(8) 0.6415(4) 0.067(2) Uani 1 1 d . . . H50A H 0.9168 0.6456 0.6171 0.080 Uiso 1 1 calc R . . H50B H 0.9288 0.5208 0.6118 0.080 Uiso 1 1 calc R . . Sb2 Sb 0.17561(5) 0.24689(7) 0.01330(3) 0.0869(3) Uani 1 1 d . . . F12 F 0.0877(9) 0.1428(13) -0.0181(6) 0.279(9) Uani 1 1 d . . . F8 F 0.2684(6) 0.3408(6) 0.0538(4) 0.129(3) Uani 1 1 d . . . F14 F 0.0782(9) 0.2529(10) 0.0800(5) 0.197(5) Uani 1 1 d . . . Sb1 Sb 0.17556(5) 0.74617(7) 0.48643(3) 0.0877(3) Uani 1 1 d . . . C33 C 0.6331(10) 0.0314(8) 1.1144(5) 0.075(3) Uani 1 1 d . . . N7 N 1.4094(9) 0.0031(8) 0.8431(5) 0.100(3) Uani 1 1 d . . . C23 C 0.2479(10) 0.1500(9) 0.5726(5) 0.098(4) Uani 1 1 d . . . H23A H 0.2900 0.0842 0.5882 0.118 Uiso 1 1 calc R . . H23B H 0.1745 0.1616 0.5967 0.118 Uiso 1 1 calc R . . C36 C 0.7785(9) 0.3611(9) 1.0045(5) 0.091(3) Uani 1 1 d . . . H36A H 0.8189 0.2942 0.9899 0.110 Uiso 1 1 calc R . . H36B H 0.8310 0.4163 0.9982 0.110 Uiso 1 1 calc R . . C22 C 0.2218(9) 0.1394(10) 0.5035(5) 0.100(4) Uani 1 1 d . . . H22A H 0.1825 0.2060 0.4872 0.120 Uiso 1 1 calc R . . H22B H 0.1693 0.0842 0.4979 0.120 Uiso 1 1 calc R . . F10 F 0.239(2) 0.3071(18) -0.0618(6) 0.372(13) Uani 1 1 d . . . F13 F 0.246(2) 0.1542(17) 0.0780(11) 0.384(14) Uani 1 1 d . . . F9 F 0.0763(12) 0.348(2) -0.0164(12) 0.417(17) Uani 1 1 d . . . F2 F 0.2667(7) 0.8425(6) 0.4468(4) 0.132(3) Uani 1 1 d . . . F3 F 0.0829(10) 0.7473(10) 0.4179(4) 0.206(5) Uani 1 1 d . . . F5 F 0.0893(10) 0.6428(13) 0.5175(6) 0.268(8) Uani 1 1 d . . . F6 F 0.2911(11) 0.6767(13) 0.5299(10) 0.274(9) Uani 1 1 d . . . F7 F 0.219(4) 0.8095(19) 0.5622(7) 0.54(3) Uani 1 1 d . . . F11 F 0.2944(10) 0.1677(9) -0.0190(11) 0.274(9) Uani 1 1 d . . . F1 F 0.0712(12) 0.851(2) 0.5117(13) 0.388(14) Uani 1 1 d . . . F4 F 0.2619(16) 0.6518(13) 0.4321(12) 0.346(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0607(4) 0.0552(4) 0.0543(4) 0.0011(3) -0.0103(3) 0.0118(3) Ag2 0.0602(4) 0.0573(5) 0.0541(4) -0.0008(3) 0.0111(3) 0.0118(3) C43 0.054(4) 0.061(5) 0.029(4) 0.003(3) 0.003(3) 0.016(4) C16 0.059(4) 0.048(5) 0.040(4) -0.010(4) 0.007(3) -0.007(3) C31 0.065(5) 0.046(5) 0.035(4) 0.013(3) -0.005(3) -0.015(4) C13 0.057(4) 0.030(4) 0.058(5) 0.012(3) -0.007(3) -0.003(3) C53 0.061(4) 0.033(4) 0.054(5) -0.011(3) 0.009(3) -0.002(3) O2 0.045(3) 0.060(4) 0.063(4) -0.010(3) 0.003(2) -0.009(2) C38 0.045(4) 0.043(5) 0.059(5) 0.008(4) 0.002(3) 0.006(3) O1 0.057(3) 0.045(3) 0.066(4) -0.007(3) -0.009(3) -0.002(2) O5 0.063(3) 0.094(5) 0.064(4) 0.020(3) 0.002(3) -0.022(3) O8 0.048(3) 0.055(4) 0.070(4) 0.013(3) 0.002(3) -0.007(2) C52 0.040(3) 0.051(5) 0.051(5) -0.004(4) 0.000(3) -0.015(3) O7 0.054(3) 0.046(3) 0.064(4) 0.003(3) 0.007(3) -0.007(2) O4 0.070(4) 0.080(4) 0.076(4) -0.026(3) -0.003(3) -0.019(3) C25 0.045(4) 0.068(6) 0.055(5) 0.004(4) -0.015(3) -0.002(4) C30 0.072(5) 0.049(5) 0.043(5) -0.005(4) -0.006(4) -0.004(4) C42 0.038(3) 0.054(5) 0.047(4) 0.002(4) 0.012(3) -0.002(3) C12 0.041(4) 0.047(5) 0.055(5) 0.003(4) 0.001(3) -0.017(3) O3 0.059(3) 0.084(5) 0.079(4) -0.012(3) 0.024(3) -0.008(3) C26 0.040(4) 0.066(6) 0.062(5) -0.010(4) -0.002(3) 0.006(3) C41 0.043(4) 0.053(5) 0.050(5) -0.003(4) 0.002(3) 0.005(3) O6 0.053(3) 0.086(5) 0.069(4) 0.014(3) -0.017(3) -0.003(3) N8 0.064(4) 0.051(5) 0.081(5) 0.011(4) 0.015(4) 0.008(3) N1 0.067(4) 0.038(4) 0.083(5) -0.006(4) -0.014(4) 0.004(3) C3 0.036(3) 0.067(5) 0.044(4) -0.005(4) -0.008(3) -0.002(3) C39 0.045(4) 0.063(6) 0.049(5) -0.001(4) 0.002(3) -0.005(3) C2 0.043(4) 0.057(5) 0.046(4) 0.001(4) 0.002(3) 0.005(3) C7 0.057(4) 0.018(5) 0.077(6) 0.000(4) -0.010(4) 0.008(3) C18 0.058(4) 0.048(5) 0.043(5) -0.006(4) 0.011(3) -0.004(3) N6 0.048(4) 0.108(7) 0.090(6) 0.008(5) 0.012(4) 0.006(4) C5 0.056(4) 0.025(4) 0.057(5) -0.010(3) -0.012(3) 0.003(3) C17 0.081(5) 0.038(5) 0.039(4) 0.000(3) 0.008(4) -0.008(4) C8 0.056(4) 0.070(6) 0.028(4) 0.004(4) -0.010(3) 0.001(4) C34 0.085(6) 0.069(6) 0.037(5) -0.002(4) -0.007(4) -0.011(5) C46 0.047(4) 0.042(5) 0.073(6) 0.002(4) 0.010(4) 0.009(3) C4 0.054(4) 0.066(6) 0.037(4) 0.002(4) 0.000(3) 0.015(4) C19 0.062(5) 0.072(6) 0.053(5) -0.022(4) 0.004(4) -0.007(4) C44 0.051(4) 0.043(5) 0.052(5) 0.011(4) 0.003(3) -0.002(3) N5 0.084(5) 0.090(6) 0.089(6) -0.042(5) 0.033(5) -0.002(5) C6 0.052(4) 0.026(4) 0.071(5) 0.000(4) 0.004(4) 0.008(3) N4 0.046(4) 0.091(6) 0.125(7) -0.001(5) -0.008(4) 0.006(4) C37 0.072(5) 0.057(6) 0.059(6) 0.006(4) -0.003(4) -0.020(4) C32 0.076(6) 0.066(6) 0.056(6) 0.012(5) -0.008(4) -0.004(5) C51 0.043(4) 0.073(6) 0.041(4) 0.013(4) -0.001(3) -0.001(4) C9 0.046(4) 0.110(8) 0.065(6) -0.043(5) -0.012(4) -0.007(4) C21 0.077(6) 0.059(6) 0.075(6) -0.015(5) 0.002(5) -0.014(4) C48 0.053(4) 0.072(6) 0.043(5) -0.003(4) 0.015(3) 0.002(4) C15 0.078(6) 0.051(5) 0.059(5) -0.012(4) 0.007(4) -0.005(4) C24 0.078(6) 0.063(6) 0.045(5) 0.011(4) 0.013(4) -0.004(5) C40 0.049(4) 0.047(5) 0.075(6) 0.002(4) 0.002(4) 0.005(3) C29 0.059(4) 0.059(5) 0.041(4) 0.005(4) -0.013(3) -0.007(4) C14 0.082(6) 0.083(7) 0.074(7) -0.031(6) 0.021(5) -0.018(5) C28 0.072(5) 0.053(5) 0.052(5) 0.015(4) -0.002(4) 0.001(4) N2 0.121(7) 0.114(7) 0.056(5) -0.039(5) 0.013(5) -0.036(6) C10 0.072(5) 0.109(8) 0.023(4) -0.012(4) 0.001(3) 0.004(5) C11 0.046(4) 0.066(6) 0.048(5) -0.007(4) 0.007(3) -0.003(4) C49 0.061(5) 0.070(6) 0.058(5) 0.037(5) 0.009(4) -0.005(4) C45 0.051(4) 0.041(5) 0.063(5) 0.003(4) -0.002(4) 0.002(3) C1 0.045(4) 0.058(5) 0.066(5) 0.001(4) 0.001(4) 0.003(3) N3 0.096(6) 0.069(6) 0.099(7) 0.038(5) -0.026(5) -0.003(5) C20 0.078(6) 0.091(8) 0.056(6) -0.022(5) 0.005(4) -0.018(5) C27 0.087(6) 0.060(6) 0.045(5) 0.019(4) -0.003(4) -0.008(5) C35 0.106(8) 0.099(9) 0.087(8) -0.013(6) -0.029(6) -0.024(7) C50 0.072(5) 0.089(7) 0.037(5) 0.017(4) 0.007(4) 0.001(5) Sb2 0.0531(3) 0.1391(7) 0.0666(4) -0.0442(4) -0.0020(3) 0.0039(4) F12 0.148(8) 0.48(2) 0.233(11) -0.248(14) 0.030(8) -0.120(11) F8 0.107(5) 0.130(6) 0.157(7) -0.030(5) 0.022(5) -0.042(4) F14 0.165(9) 0.296(13) 0.151(8) -0.114(8) 0.047(7) -0.117(9) Sb1 0.0533(3) 0.1389(7) 0.0675(5) 0.0445(4) 0.0032(3) 0.0037(4) C33 0.107(8) 0.063(7) 0.055(7) 0.027(5) -0.026(5) -0.012(5) N7 0.126(8) 0.118(8) 0.062(6) 0.047(6) -0.020(5) -0.038(6) C23 0.094(8) 0.107(9) 0.097(9) 0.007(7) 0.029(7) -0.032(7) C36 0.070(6) 0.121(9) 0.092(8) 0.013(6) -0.020(5) -0.049(6) C22 0.081(7) 0.153(11) 0.077(8) -0.011(7) 0.021(6) -0.068(7) F10 0.46(3) 0.52(3) 0.111(9) 0.045(13) 0.035(13) 0.08(3) F13 0.41(3) 0.36(3) 0.40(3) 0.17(2) -0.19(2) -0.13(2) F9 0.128(10) 0.56(3) 0.56(3) 0.39(3) -0.082(15) -0.013(15) F2 0.112(5) 0.116(6) 0.174(7) 0.028(5) -0.016(5) -0.041(4) F3 0.211(11) 0.294(13) 0.135(7) 0.096(8) -0.063(7) -0.146(10) F5 0.162(9) 0.43(2) 0.226(12) 0.227(14) -0.023(8) -0.122(11) F6 0.139(9) 0.284(18) 0.40(2) 0.165(17) -0.109(12) -0.051(10) F7 0.99(8) 0.41(3) 0.138(12) -0.071(14) -0.02(2) 0.32(4) F11 0.119(8) 0.140(9) 0.56(3) -0.096(13) 0.068(12) 0.011(6) F1 0.116(9) 0.54(3) 0.50(3) -0.27(3) 0.042(14) 0.034(14) F4 0.251(18) 0.225(15) 0.55(3) -0.058(18) 0.16(2) 0.048(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 Ag1 N1 2.211(7) . ? Ag1 N3 2.247(8) . ? Ag1 N2 2.288(7) . ? Ag1 N4 2.507(8) . ? Ag2 N8 2.228(7) . ? Ag2 N5 2.252(7) . ? Ag2 N7 2.269(9) . ? Ag2 N6 2.489(8) . ? C43 C42 1.516(10) . ? C43 C44 1.536(10) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C16 C15 1.498(10) . ? C16 C17 1.505(10) . ? C16 C25 1.559(11) . ? C16 H16 0.9800 . ? C31 C30 1.486(10) . ? C31 C32 1.502(11) . ? C31 C39 1.558(11) . ? C31 H31 0.9800 . ? C13 C5 1.506(10) . ? C13 C12 1.550(10) . ? C13 C8 1.573(10) . ? C13 H13 0.9800 . ? C53 C44 1.538(10) . ? C53 C52 1.548(10) . ? C53 C48 1.584(11) . ? C53 H53 0.9800 . ? O2 C6 1.413(9) . ? O2 C8 1.425(9) . ? C38 C37 1.536(11) . ? C38 C29 1.542(10) . ? C38 C39 1.546(11) . ? C38 H38 0.9800 . ? O1 C2 1.399(8) . ? O1 C11 1.427(10) . ? O5 C28 1.427(10) . ? O5 C37 1.461(10) . ? O8 C45 1.383(9) . ? O8 C48 1.448(9) . ? C52 C42 1.537(10) . ? C52 C51 1.549(11) . ? C52 H52 0.9800 . ? O7 C41 1.397(9) . ? O7 C51 1.425(9) . ? O4 C19 1.408(11) . ? O4 C21 1.520(11) . ? C25 C24 1.511(11) . ? C25 C26 1.550(11) . ? C25 H25 0.9800 . ? C30 C29 1.536(10) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C42 C41 1.512(10) . ? C42 H42 0.9800 . ? C12 C11 1.534(10) . ? C12 C3 1.561(10) . ? C12 H12 0.9800 . ? O3 C15 1.406(10) . ? O3 C24 1.419(10) . ? C26 C21 1.539(12) . ? C26 C18 1.541(11) . ? C26 H26 0.9800 . ? C41 C40 1.486(10) . ? C41 H41 0.9800 . ? O6 C32 1.415(11) . ? O6 C34 1.424(10) . ? N8 C46 1.120(9) . ? N1 C7 1.114(9) . ? C3 C4 1.512(10) . ? C3 C2 1.529(10) . ? C3 H3 0.9800 . ? C39 C34 1.543(11) . ? C39 H39 0.9800 . ? C2 C1 1.498(10) . ? C2 H2 0.9800 . ? C7 C6 1.482(10) . ? C18 C19 1.538(10) . ? C18 C17 1.543(10) . ? C18 H18 0.9800 . ? N6 C1 1.124(10) 1_745 ? C5 C6 1.515(10) . ? C5 C4 1.536(10) . ? C5 H5 0.9800 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C8 C9 1.535(11) . ? C8 H8 0.9800 . ? C34 C35 1.524(14) . ? C34 H34 0.9800 . ? C46 C45 1.484(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C19 C20 1.498(12) . ? C44 C45 1.504(10) . ? C44 H44 0.9800 . ? N5 C20 1.125(11) 2_756 ? C6 H6 0.9800 . ? N4 C40 1.129(10) . ? C37 C36 1.539(12) . ? C37 H37 0.9800 . ? C32 C33 1.478(15) . ? C32 H32 0.9800 . ? C51 C50 1.502(10) . ? C51 H51 0.9800 . ? C9 C10 1.504(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C21 C22 1.513(13) . ? C21 H21 0.9800 . ? C48 C49 1.495(11) . ? C48 H48 0.9800 . ? C15 C14 1.495(13) . ? C15 H15 0.9800 . ? C24 C23 1.534(13) . ? C24 H24 0.9800 . ? C29 C28 1.492(11) . ? C29 H29 0.9800 . ? C14 N2 1.122(11) . ? C28 C27 1.477(12) . ? C28 H28 0.9800 . ? C10 C11 1.516(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11 0.9800 . ? C49 C50 1.504(12) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C45 H45 0.9800 . ? C1 N6 1.124(10) 1_365 ? N3 C27 1.139(11) . ? C20 N5 1.125(11) 2_756 ? C35 C36 1.473(14) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? Sb2 F9 1.726(14) . ? Sb2 F11 1.735(9) . ? Sb2 F14 1.764(8) . ? Sb2 F12 1.852(10) . ? Sb2 F8 1.870(7) . ? Sb2 F10 1.896(17) . ? Sb2 F13 1.899(16) . ? Sb1 F6 1.756(10) . ? Sb1 F3 1.772(8) . ? Sb1 F7 1.86(2) . ? Sb1 F1 1.771(16) . ? Sb1 F5 1.820(10) . ? Sb1 F4 1.851(14) . ? Sb1 F2 1.857(7) . ? C33 N7 1.108(12) 2_757 ? N7 C33 1.108(12) 2_757 ? C23 C22 1.472(14) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 N3 153.0(3) . . ? N1 Ag1 N2 102.8(3) . . ? N3 Ag1 N2 100.7(4) . . ? N1 Ag1 N4 99.4(3) . . ? N3 Ag1 N4 84.3(3) . . ? N2 Ag1 N4 111.2(3) . . ? N8 Ag2 N5 153.1(3) . . ? N8 Ag2 N7 103.2(3) . . ? N5 Ag2 N7 100.3(4) . . ? N8 Ag2 N6 98.7(3) . . ? N5 Ag2 N6 85.1(3) . . ? N7 Ag2 N6 110.1(3) . . ? C42 C43 C44 105.5(6) . . ? C42 C43 H43A 110.6 . . ? C44 C43 H43A 110.6 . . ? C42 C43 H43B 110.6 . . ? C44 C43 H43B 110.6 . . ? H43A C43 H43B 108.8 . . ? C15 C16 C17 113.6(7) . . ? C15 C16 C25 103.5(6) . . ? C17 C16 C25 105.6(6) . . ? C15 C16 H16 111.2 . . ? C17 C16 H16 111.2 . . ? C25 C16 H16 111.2 . . ? C30 C31 C32 114.8(7) . . ? C30 C31 C39 104.8(6) . . ? C32 C31 C39 103.2(6) . . ? C30 C31 H31 111.2 . . ? C32 C31 H31 111.2 . . ? C39 C31 H31 111.2 . . ? C5 C13 C12 106.5(6) . . ? C5 C13 C8 102.9(6) . . ? C12 C13 C8 117.2(6) . . ? C5 C13 H13 109.9 . . ? C12 C13 H13 109.9 . . ? C8 C13 H13 109.9 . . ? C44 C53 C52 105.7(6) . . ? C44 C53 C48 102.1(6) . . ? C52 C53 C48 117.5(6) . . ? C44 C53 H53 110.3 . . ? C52 C53 H53 110.3 . . ? C48 C53 H53 110.3 . . ? C6 O2 C8 106.8(6) . . ? C37 C38 C29 105.6(6) . . ? C37 C38 C39 117.4(6) . . ? C29 C38 C39 104.1(6) . . ? C37 C38 H38 109.8 . . ? C29 C38 H38 109.8 . . ? C39 C38 H38 109.8 . . ? C2 O1 C11 106.3(6) . . ? C28 O5 C37 109.8(6) . . ? C45 O8 C48 108.8(6) . . ? C42 C52 C53 106.8(6) . . ? C42 C52 C51 102.6(6) . . ? C53 C52 C51 117.1(6) . . ? C42 C52 H52 110.0 . . ? C53 C52 H52 110.0 . . ? C51 C52 H52 110.0 . . ? C41 O7 C51 107.1(5) . . ? C19 O4 C21 108.5(6) . . ? C24 C25 C26 116.9(7) . . ? C24 C25 C16 103.8(6) . . ? C26 C25 C16 107.0(6) . . ? C24 C25 H25 109.6 . . ? C26 C25 H25 109.6 . . ? C16 C25 H25 109.6 . . ? C31 C30 C29 104.6(6) . . ? C31 C30 H30A 110.8 . . ? C29 C30 H30A 110.8 . . ? C31 C30 H30B 110.8 . . ? C29 C30 H30B 110.8 . . ? H30A C30 H30B 108.9 . . ? C41 C42 C43 113.9(6) . . ? C41 C42 C52 104.8(6) . . ? C43 C42 C52 105.6(5) . . ? C41 C42 H42 110.7 . . ? C43 C42 H42 110.7 . . ? C52 C42 H42 110.7 . . ? C11 C12 C13 118.2(6) . . ? C11 C12 C3 102.7(6) . . ? C13 C12 C3 106.1(6) . . ? C11 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C3 C12 H12 109.8 . . ? C15 O3 C24 108.1(6) . . ? C21 C26 C18 105.2(6) . . ? C21 C26 C25 118.5(6) . . ? C18 C26 C25 103.7(6) . . ? C21 C26 H26 109.6 . . ? C18 C26 H26 109.6 . . ? C25 C26 H26 109.6 . . ? O7 C41 C40 109.1(6) . . ? O7 C41 C42 106.1(5) . . ? C40 C41 C42 112.3(6) . . ? O7 C41 H41 109.7 . . ? C40 C41 H41 109.7 . . ? C42 C41 H41 109.7 . . ? C32 O6 C34 108.0(6) . . ? C46 N8 Ag2 173.3(7) . . ? C7 N1 Ag1 173.3(7) . . ? C4 C3 C2 114.2(7) . . ? C4 C3 C12 104.5(5) . . ? C2 C3 C12 103.4(6) . . ? C4 C3 H3 111.4 . . ? C2 C3 H3 111.4 . . ? C12 C3 H3 111.4 . . ? C34 C39 C38 117.6(7) . . ? C34 C39 C31 104.2(6) . . ? C38 C39 C31 107.1(6) . . ? C34 C39 H39 109.2 . . ? C38 C39 H39 109.2 . . ? C31 C39 H39 109.2 . . ? O1 C2 C1 108.9(6) . . ? O1 C2 C3 107.3(6) . . ? C1 C2 C3 111.0(6) . . ? O1 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? N1 C7 C6 178.1(8) . . ? C19 C18 C26 103.0(6) . . ? C19 C18 C17 114.3(6) . . ? C26 C18 C17 105.3(6) . . ? C19 C18 H18 111.3 . . ? C26 C18 H18 111.3 . . ? C17 C18 H18 111.3 . . ? C1 N6 Ag2 145.9(8) 1_745 . ? C13 C5 C6 103.4(6) . . ? C13 C5 C4 103.4(5) . . ? C6 C5 C4 110.6(6) . . ? C13 C5 H5 112.9 . . ? C6 C5 H5 112.9 . . ? C4 C5 H5 112.9 . . ? C16 C17 C18 102.8(6) . . ? C16 C17 H17A 111.2 . . ? C18 C17 H17A 111.2 . . ? C16 C17 H17B 111.2 . . ? C18 C17 H17B 111.2 . . ? H17A C17 H17B 109.1 . . ? O2 C8 C9 106.9(7) . . ? O2 C8 C13 106.8(5) . . ? C9 C8 C13 116.8(6) . . ? O2 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C13 C8 H8 108.7 . . ? O6 C34 C35 108.8(8) . . ? O6 C34 C39 105.8(6) . . ? C35 C34 C39 116.0(7) . . ? O6 C34 H34 108.7 . . ? C35 C34 H34 108.7 . . ? C39 C34 H34 108.7 . . ? N8 C46 C45 176.4(9) . . ? C3 C4 C5 105.8(6) . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4B 110.6 . . ? C5 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? O4 C19 C20 108.8(7) . . ? O4 C19 C18 105.8(6) . . ? C20 C19 C18 109.7(7) . . ? C45 C44 C43 110.8(6) . . ? C45 C44 C53 103.8(6) . . ? C43 C44 C53 103.2(5) . . ? C45 C44 H44 112.8 . . ? C43 C44 H44 112.8 . . ? C53 C44 H44 112.8 . . ? C20 N5 Ag2 156.2(8) 2_756 . ? O2 C6 C7 107.9(6) . . ? O2 C6 C5 105.1(5) . . ? C7 C6 C5 112.4(6) . . ? O2 C6 H6 110.5 . . ? C7 C6 H6 110.5 . . ? C5 C6 H6 110.5 . . ? C40 N4 Ag1 145.7(7) . . ? O5 C37 C38 104.6(6) . . ? O5 C37 C36 105.5(7) . . ? C38 C37 C36 116.5(7) . . ? O5 C37 H37 110.0 . . ? C38 C37 H37 110.0 . . ? C36 C37 H37 110.0 . . ? O6 C32 C33 111.6(7) . . ? O6 C32 C31 106.0(7) . . ? C33 C32 C31 110.7(8) . . ? O6 C32 H32 109.5 . . ? C33 C32 H32 109.5 . . ? C31 C32 H32 109.5 . . ? O7 C51 C50 108.0(7) . . ? O7 C51 C52 106.8(6) . . ? C50 C51 C52 113.8(6) . . ? O7 C51 H51 109.4 . . ? C50 C51 H51 109.4 . . ? C52 C51 H51 109.4 . . ? C10 C9 C8 111.9(8) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C22 C21 O4 103.2(8) . . ? C22 C21 C26 116.5(7) . . ? O4 C21 C26 105.3(7) . . ? C22 C21 H21 110.5 . . ? O4 C21 H21 110.5 . . ? C26 C21 H21 110.5 . . ? O8 C48 C49 108.4(7) . . ? O8 C48 C53 105.6(6) . . ? C49 C48 C53 116.5(6) . . ? O8 C48 H48 108.7 . . ? C49 C48 H48 108.7 . . ? C53 C48 H48 108.7 . . ? O3 C15 C14 111.0(7) . . ? O3 C15 C16 105.6(6) . . ? C14 C15 C16 110.0(7) . . ? O3 C15 H15 110.1 . . ? C14 C15 H15 110.1 . . ? C16 C15 H15 110.1 . . ? O3 C24 C25 107.0(6) . . ? O3 C24 C23 106.5(8) . . ? C25 C24 C23 116.3(7) . . ? O3 C24 H24 109.0 . . ? C25 C24 H24 108.9 . . ? C23 C24 H24 109.0 . . ? N4 C40 C41 176.0(10) . . ? C28 C29 C30 115.1(7) . . ? C28 C29 C38 102.4(7) . . ? C30 C29 C38 104.1(6) . . ? C28 C29 H29 111.5 . . ? C30 C29 H29 111.5 . . ? C38 C29 H29 111.5 . . ? N2 C14 C15 177.6(10) . . ? O5 C28 C27 109.8(7) . . ? O5 C28 C29 105.8(6) . . ? C27 C28 C29 109.2(7) . . ? O5 C28 H28 110.6 . . ? C27 C28 H28 110.6 . . ? C29 C28 H28 110.6 . . ? C14 N2 Ag1 147.8(9) . . ? C9 C10 C11 110.6(6) . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O1 C11 C10 106.8(7) . . ? O1 C11 C12 108.3(6) . . ? C10 C11 C12 114.5(6) . . ? O1 C11 H11 109.0 . . ? C10 C11 H11 109.0 . . ? C12 C11 H11 109.0 . . ? C48 C49 C50 112.1(7) . . ? C48 C49 H49A 109.2 . . ? C50 C49 H49A 109.2 . . ? C48 C49 H49B 109.2 . . ? C50 C49 H49B 109.2 . . ? H49A C49 H49B 107.9 . . ? O8 C45 C46 107.5(6) . . ? O8 C45 C44 105.3(6) . . ? C46 C45 C44 111.9(6) . . ? O8 C45 H45 110.6 . . ? C46 C45 H45 110.7 . . ? C44 C45 H45 110.6 . . ? N6 C1 C2 177.2(9) 1_365 . ? C27 N3 Ag1 157.0(9) . . ? N5 C20 C19 179.3(10) 2_756 . ? N3 C27 C28 176.4(10) . . ? C36 C35 C34 109.6(8) . . ? C36 C35 H35A 109.7 . . ? C34 C35 H35A 109.7 . . ? C36 C35 H35B 109.8 . . ? C34 C35 H35B 109.8 . . ? H35A C35 H35B 108.2 . . ? C51 C50 C49 110.8(6) . . ? C51 C50 H50A 109.5 . . ? C49 C50 H50A 109.5 . . ? C51 C50 H50B 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 108.1 . . ? F9 Sb2 F11 134.8(10) . . ? F9 Sb2 F14 83.1(9) . . ? F11 Sb2 F14 141.0(8) . . ? F9 Sb2 F12 91.8(10) . . ? F11 Sb2 F12 84.3(5) . . ? F14 Sb2 F12 85.9(4) . . ? F9 Sb2 F8 93.8(9) . . ? F11 Sb2 F8 94.7(5) . . ? F14 Sb2 F8 90.6(3) . . ? F12 Sb2 F8 172.9(6) . . ? F9 Sb2 F10 70.6(8) . . ? F11 Sb2 F10 67.0(8) . . ? F14 Sb2 F10 151.8(7) . . ? F12 Sb2 F10 104.3(8) . . ? F8 Sb2 F10 81.7(8) . . ? F9 Sb2 F13 155.2(12) . . ? F11 Sb2 F13 69.9(10) . . ? F14 Sb2 F13 72.9(9) . . ? F12 Sb2 F13 92.5(8) . . ? F8 Sb2 F13 80.5(7) . . ? F10 Sb2 F13 131.4(11) . . ? F6 Sb1 F3 146.4(9) . . ? F6 Sb1 F7 63.9(9) . . ? F3 Sb1 F7 149.7(9) . . ? F6 Sb1 F1 129.5(10) . . ? F3 Sb1 F1 83.0(9) . . ? F7 Sb1 F1 67.3(9) . . ? F6 Sb1 F5 84.2(5) . . ? F3 Sb1 F5 85.3(5) . . ? F7 Sb1 F5 101.7(12) . . ? F1 Sb1 F5 93.5(10) . . ? F6 Sb1 F4 70.5(9) . . ? F3 Sb1 F4 78.1(9) . . ? F7 Sb1 F4 130.2(12) . . ? F1 Sb1 F4 159.6(11) . . ? F5 Sb1 F4 92.3(8) . . ? F6 Sb1 F2 96.1(5) . . ? F3 Sb1 F2 91.1(4) . . ? F7 Sb1 F2 84.0(11) . . ? F1 Sb1 F2 91.1(10) . . ? F5 Sb1 F2 173.8(6) . . ? F4 Sb1 F2 82.0(6) . . ? N7 C33 C32 176.6(11) 2_757 . ? C33 N7 Ag2 146.8(9) 2_757 . ? C22 C23 C24 111.7(9) . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C35 C36 C37 111.0(9) . . ? C35 C36 H36A 109.4 . . ? C37 C36 H36A 109.4 . . ? C35 C36 H36B 109.5 . . ? C37 C36 H36B 109.5 . . ? H36A C36 H36B 108.0 . . ? C23 C22 C21 110.3(9) . . ? C23 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? C23 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C44 C53 C52 C42 12.1(8) . . . . ? C48 C53 C52 C42 -101.0(7) . . . . ? C44 C53 C52 C51 126.4(7) . . . . ? C48 C53 C52 C51 13.3(9) . . . . ? C15 C16 C25 C24 11.4(8) . . . . ? C17 C16 C25 C24 -108.3(7) . . . . ? C15 C16 C25 C26 135.6(6) . . . . ? C17 C16 C25 C26 15.9(8) . . . . ? C32 C31 C30 C29 -146.7(7) . . . . ? C39 C31 C30 C29 -34.1(8) . . . . ? C44 C43 C42 C41 -144.1(6) . . . . ? C44 C43 C42 C52 -29.7(8) . . . . ? C53 C52 C42 C41 131.3(6) . . . . ? C51 C52 C42 C41 7.6(7) . . . . ? C53 C52 C42 C43 10.7(8) . . . . ? C51 C52 C42 C43 -113.0(6) . . . . ? C5 C13 C12 C11 -126.4(7) . . . . ? C8 C13 C12 C11 -11.9(10) . . . . ? C5 C13 C12 C3 -11.8(7) . . . . ? C8 C13 C12 C3 102.7(7) . . . . ? C24 C25 C26 C21 8.4(11) . . . . ? C16 C25 C26 C21 -107.4(8) . . . . ? C24 C25 C26 C18 124.5(7) . . . . ? C16 C25 C26 C18 8.7(7) . . . . ? C51 O7 C41 C40 -84.2(7) . . . . ? C51 O7 C41 C42 37.0(7) . . . . ? C43 C42 C41 O7 87.9(7) . . . . ? C52 C42 C41 O7 -27.1(7) . . . . ? C43 C42 C41 C40 -152.9(6) . . . . ? C52 C42 C41 C40 92.1(7) . . . . ? N5 Ag2 N8 C46 -166(6) . . . . ? N7 Ag2 N8 C46 43(6) . . . . ? N6 Ag2 N8 C46 -70(6) . . . . ? N3 Ag1 N1 C7 149(5) . . . . ? N2 Ag1 N1 C7 -61(6) . . . . ? N4 Ag1 N1 C7 53(6) . . . . ? C11 C12 C3 C4 113.2(7) . . . . ? C13 C12 C3 C4 -11.5(8) . . . . ? C11 C12 C3 C2 -6.6(7) . . . . ? C13 C12 C3 C2 -131.3(6) . . . . ? C37 C38 C39 C34 9.0(10) . . . . ? C29 C38 C39 C34 125.2(7) . . . . ? C37 C38 C39 C31 -107.8(7) . . . . ? C29 C38 C39 C31 8.5(7) . . . . ? C30 C31 C39 C34 -109.4(7) . . . . ? C32 C31 C39 C34 11.1(8) . . . . ? C30 C31 C39 C38 15.9(8) . . . . ? C32 C31 C39 C38 136.4(6) . . . . ? C11 O1 C2 C1 84.2(7) . . . . ? C11 O1 C2 C3 -36.0(7) . . . . ? C4 C3 C2 O1 -86.9(7) . . . . ? C12 C3 C2 O1 26.0(7) . . . . ? C4 C3 C2 C1 154.1(6) . . . . ? C12 C3 C2 C1 -93.0(7) . . . . ? Ag1 N1 C7 C6 -108(27) . . . . ? C21 C26 C18 C19 -24.8(7) . . . . ? C25 C26 C18 C19 -149.9(6) . . . . ? C21 C26 C18 C17 95.3(7) . . . . ? C25 C26 C18 C17 -29.9(7) . . . . ? N8 Ag2 N6 C1 154.5(13) . . . 1_745 ? N5 Ag2 N6 C1 -52.2(13) . . . 1_745 ? N7 Ag2 N6 C1 46.9(14) . . . 1_745 ? C12 C13 C5 C6 145.5(6) . . . . ? C8 C13 C5 C6 21.6(7) . . . . ? C12 C13 C5 C4 30.1(7) . . . . ? C8 C13 C5 C4 -93.8(7) . . . . ? C15 C16 C17 C18 -146.8(7) . . . . ? C25 C16 C17 C18 -34.0(7) . . . . ? C19 C18 C17 C16 152.4(7) . . . . ? C26 C18 C17 C16 40.2(7) . . . . ? C6 O2 C8 C9 -149.7(6) . . . . ? C6 O2 C8 C13 -23.9(7) . . . . ? C5 C13 C8 O2 0.1(7) . . . . ? C12 C13 C8 O2 -116.3(7) . . . . ? C5 C13 C8 C9 119.8(7) . . . . ? C12 C13 C8 C9 3.3(10) . . . . ? C32 O6 C34 C35 -155.0(7) . . . . ? C32 O6 C34 C39 -29.7(8) . . . . ? C38 C39 C34 O6 -108.1(7) . . . . ? C31 C39 C34 O6 10.2(8) . . . . ? C38 C39 C34 C35 12.6(11) . . . . ? C31 C39 C34 C35 130.9(8) . . . . ? Ag2 N8 C46 C45 119(13) . . . . ? C2 C3 C4 C5 142.6(6) . . . . ? C12 C3 C4 C5 30.3(8) . . . . ? C13 C5 C4 C3 -38.0(7) . . . . ? C6 C5 C4 C3 -148.2(6) . . . . ? C21 O4 C19 C20 85.6(7) . . . . ? C21 O4 C19 C18 -32.2(8) . . . . ? C26 C18 C19 O4 35.4(8) . . . . ? C17 C18 C19 O4 -78.1(8) . . . . ? C26 C18 C19 C20 -81.8(8) . . . . ? C17 C18 C19 C20 164.6(7) . . . . ? C42 C43 C44 C45 147.6(7) . . . . ? C42 C43 C44 C53 37.0(8) . . . . ? C52 C53 C44 C45 -145.5(6) . . . . ? C48 C53 C44 C45 -22.0(7) . . . . ? C52 C53 C44 C43 -29.8(7) . . . . ? C48 C53 C44 C43 93.6(7) . . . . ? N8 Ag2 N5 C20 148(2) . . . 2_756 ? N7 Ag2 N5 C20 -61(2) . . . 2_756 ? N6 Ag2 N5 C20 49(2) . . . 2_756 ? C8 O2 C6 C7 -81.6(7) . . . . ? C8 O2 C6 C5 38.4(7) . . . . ? N1 C7 C6 O2 10(28) . . . . ? N1 C7 C6 C5 -105(27) . . . . ? C13 C5 C6 O2 -37.4(7) . . . . ? C4 C5 C6 O2 72.8(8) . . . . ? C13 C5 C6 C7 79.7(7) . . . . ? C4 C5 C6 C7 -170.2(6) . . . . ? N1 Ag1 N4 C40 -155.4(14) . . . . ? N3 Ag1 N4 C40 51.7(14) . . . . ? N2 Ag1 N4 C40 -47.6(15) . . . . ? C28 O5 C37 C38 14.8(8) . . . . ? C28 O5 C37 C36 138.2(7) . . . . ? C29 C38 C37 O5 7.2(8) . . . . ? C39 C38 C37 O5 122.6(7) . . . . ? C29 C38 C37 C36 -108.8(8) . . . . ? C39 C38 C37 C36 6.6(11) . . . . ? C34 O6 C32 C33 -82.8(8) . . . . ? C34 O6 C32 C31 37.9(8) . . . . ? C30 C31 C32 O6 84.3(8) . . . . ? C39 C31 C32 O6 -29.2(8) . . . . ? C30 C31 C32 C33 -154.6(7) . . . . ? C39 C31 C32 C33 91.9(8) . . . . ? C41 O7 C51 C50 -154.7(6) . . . . ? C41 O7 C51 C52 -31.9(7) . . . . ? C42 C52 C51 O7 13.6(7) . . . . ? C53 C52 C51 O7 -102.9(7) . . . . ? C42 C52 C51 C50 132.7(7) . . . . ? C53 C52 C51 C50 16.1(9) . . . . ? O2 C8 C9 C10 153.3(7) . . . . ? C13 C8 C9 C10 33.8(10) . . . . ? C19 O4 C21 C22 138.5(7) . . . . ? C19 O4 C21 C26 15.9(8) . . . . ? C18 C26 C21 C22 -106.8(9) . . . . ? C25 C26 C21 C22 8.5(13) . . . . ? C18 C26 C21 O4 6.8(8) . . . . ? C25 C26 C21 O4 122.1(7) . . . . ? C45 O8 C48 C49 148.2(6) . . . . ? C45 O8 C48 C53 22.7(7) . . . . ? C44 C53 C48 O8 1.1(7) . . . . ? C52 C53 C48 O8 116.2(7) . . . . ? C44 C53 C48 C49 -119.2(7) . . . . ? C52 C53 C48 C49 -4.1(10) . . . . ? C24 O3 C15 C14 -82.7(8) . . . . ? C24 O3 C15 C16 36.4(8) . . . . ? C17 C16 C15 O3 85.4(8) . . . . ? C25 C16 C15 O3 -28.6(8) . . . . ? C17 C16 C15 C14 -154.8(7) . . . . ? C25 C16 C15 C14 91.1(8) . . . . ? C15 O3 C24 C25 -28.7(8) . . . . ? C15 O3 C24 C23 -153.7(7) . . . . ? C26 C25 C24 O3 -108.2(8) . . . . ? C16 C25 C24 O3 9.4(8) . . . . ? C26 C25 C24 C23 10.6(11) . . . . ? C16 C25 C24 C23 128.2(8) . . . . ? Ag1 N4 C40 C41 64(14) . . . . ? O7 C41 C40 N4 24(14) . . . . ? C42 C41 C40 N4 -94(13) . . . . ? C31 C30 C29 C28 151.3(7) . . . . ? C31 C30 C29 C38 40.0(8) . . . . ? C37 C38 C29 C28 -25.0(7) . . . . ? C39 C38 C29 C28 -149.3(6) . . . . ? C37 C38 C29 C30 95.3(7) . . . . ? C39 C38 C29 C30 -29.0(7) . . . . ? O3 C15 C14 N2 133(29) . . . . ? C16 C15 C14 N2 17(30) . . . . ? C37 O5 C28 C27 85.9(8) . . . . ? C37 O5 C28 C29 -31.8(8) . . . . ? C30 C29 C28 O5 -77.9(8) . . . . ? C38 C29 C28 O5 34.3(8) . . . . ? C30 C29 C28 C27 163.9(7) . . . . ? C38 C29 C28 C27 -83.8(8) . . . . ? C15 C14 N2 Ag1 172(28) . . . . ? N1 Ag1 N2 C14 -59.9(18) . . . . ? N3 Ag1 N2 C14 106.6(18) . . . . ? N4 Ag1 N2 C14 -165.4(17) . . . . ? C8 C9 C10 C11 -63.5(10) . . . . ? C2 O1 C11 C10 155.3(6) . . . . ? C2 O1 C11 C12 31.6(7) . . . . ? C9 C10 C11 O1 -64.9(9) . . . . ? C9 C10 C11 C12 55.0(10) . . . . ? C13 C12 C11 O1 102.2(7) . . . . ? C3 C12 C11 O1 -14.2(7) . . . . ? C13 C12 C11 C10 -16.9(10) . . . . ? C3 C12 C11 C10 -133.2(7) . . . . ? O8 C48 C49 C50 -153.0(7) . . . . ? C53 C48 C49 C50 -34.2(10) . . . . ? C48 O8 C45 C46 81.6(7) . . . . ? C48 O8 C45 C44 -37.9(7) . . . . ? N8 C46 C45 O8 -2(14) . . . . ? N8 C46 C45 C44 113(14) . . . . ? C43 C44 C45 O8 -73.0(8) . . . . ? C53 C44 C45 O8 37.2(7) . . . . ? C43 C44 C45 C46 170.5(6) . . . . ? C53 C44 C45 C46 -79.3(8) . . . . ? O1 C2 C1 N6 -14(20) . . . 1_365 ? C3 C2 C1 N6 104(19) . . . 1_365 ? N1 Ag1 N3 C27 -155.6(19) . . . . ? N2 Ag1 N3 C27 54(2) . . . . ? N4 Ag1 N3 C27 -56(2) . . . . ? O4 C19 C20 N5 -140(100) . . . 2_756 ? C18 C19 C20 N5 -24(100) . . . 2_756 ? Ag1 N3 C27 C28 91(16) . . . . ? O5 C28 C27 N3 -20(17) . . . . ? C29 C28 C27 N3 95(16) . . . . ? O6 C34 C35 C36 68.9(10) . . . . ? C39 C34 C35 C36 -50.2(12) . . . . ? O7 C51 C50 C49 62.9(9) . . . . ? C52 C51 C50 C49 -55.5(10) . . . . ? C48 C49 C50 C51 65.4(10) . . . . ? O6 C32 C33 N7 106(19) . . . 2_757 ? C31 C32 C33 N7 -12(19) . . . 2_757 ? N8 Ag2 N7 C33 58.7(17) . . . 2_757 ? N5 Ag2 N7 C33 -108.2(17) . . . 2_757 ? N6 Ag2 N7 C33 163.3(16) . . . 2_757 ? O3 C24 C23 C22 71.4(10) . . . . ? C25 C24 C23 C22 -47.7(13) . . . . ? C34 C35 C36 C37 65.8(12) . . . . ? O5 C37 C36 C35 -160.1(8) . . . . ? C38 C37 C36 C35 -44.6(12) . . . . ? C24 C23 C22 C21 64.1(13) . . . . ? O4 C21 C22 C23 -159.3(8) . . . . ? C26 C21 C22 C23 -44.5(13) . . . . ? _diffrn_measured_fraction_theta_max 0.815 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.815 _refine_diff_density_max 0.912 _refine_diff_density_min -1.404 _refine_diff_density_rms 0.110 _vrf_PLAT029_new ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.815 RESPONSE: : Even though crystal data was collected up to 0.73 \%A resolution, the crystal (the largest available) still diffracted quite weakly at high angle. On repeated recrystallisation we could get only small sized crystals. ; _vrf_PLAT234_new ; PROBLEM: Large Hirshfeld Difference Sb1 -- F7 .. 0.44 Ang. RESPONSE: This alarm is due to the elongated ADPs of Sb atom and Fluorine (F7)which suggest that these are probably disordered. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 942147' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 Ag N4 O4, F6 P' _chemical_formula_sum 'C26 H28 Ag F6 N4 O4 P' _chemical_formula_weight 713.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 11.3548(5) _cell_length_b 20.4728(7) _cell_length_c 12.5381(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.9590(10) _cell_angle_gamma 90.00 _cell_volume 2898.91(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6647 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.59 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7603 _exptl_absorpt_correction_T_max 0.8518 _exptl_absorpt_process_details 'SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22780 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.42 _reflns_number_total 7005 _reflns_number_gt 4644 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1214P)^2^+2.2654P] 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 7005 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.2156 _refine_ls_wR_factor_gt 0.1916 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.052 _refine_ls_shift/su_mean 0.005 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 0.88910(4) 0.745347(17) 0.90356(3) 0.05925(18) Uani 1 1 d . . . C1 C 0.8876(5) 1.1296(2) 1.3138(4) 0.0637(13) Uani 1 1 d . . . H1 H 0.8585 1.1638 1.2631 0.076 Uiso 1 1 calc R . . C2 C 0.8213(5) 1.0321(3) 1.3841(4) 0.0684(14) Uani 1 1 d . . . H2 H 0.8413 1.0275 1.4617 0.082 Uiso 1 1 calc R . . C3 C 0.7107(6) 0.9925(3) 1.3493(7) 0.099(2) Uani 1 1 d . . . H3A H 0.6553 0.9969 1.4029 0.119 Uiso 1 1 calc R . . H3B H 0.6731 1.0099 1.2823 0.119 Uiso 1 1 calc R . . C4 C 0.7370(8) 0.9234(4) 1.3353(6) 0.106(3) Uani 1 1 d . . . H4A H 0.6637 0.8991 1.3220 0.128 Uiso 1 1 calc R . . H4B H 0.7801 0.9066 1.4003 0.128 Uiso 1 1 calc R . . C5 C 0.8084(6) 0.9145(3) 1.2445(5) 0.0737(16) Uani 1 1 d . . . H5 H 0.8332 0.8687 1.2437 0.088 Uiso 1 1 calc R . . C6 C 0.8161(5) 0.9474(2) 1.0690(4) 0.0595(12) Uani 1 1 d . . . H6 H 0.7746 0.9744 1.0126 0.071 Uiso 1 1 calc R . . C7 C 0.9124(4) 0.9870(2) 1.1332(3) 0.0505(10) Uani 1 1 d . . . H7 H 0.9883 0.9825 1.1031 0.061 Uiso 1 1 calc R . . C8 C 0.8816(4) 1.0582(2) 1.1470(3) 0.0510(11) Uani 1 1 d . . . H8A H 0.7968 1.0640 1.1468 0.061 Uiso 1 1 calc R . . H8B H 0.9093 1.0847 1.0906 0.061 Uiso 1 1 calc R . . C9 C 0.9463(4) 1.0758(2) 1.2559(4) 0.0529(11) Uani 1 1 d . . . H9 H 1.0302 1.0852 1.2508 0.063 Uiso 1 1 calc R . . C10 C 0.9303(4) 1.0154(2) 1.3262(4) 0.0524(10) Uani 1 1 d . . . H10 H 0.9999 1.0096 1.3785 0.063 Uiso 1 1 calc R . . C11 C 0.9190(5) 0.9570(2) 1.2467(4) 0.0564(11) Uani 1 1 d . . . H11 H 0.9897 0.9294 1.2588 0.068 Uiso 1 1 calc R . . C12 C 0.8676(6) 0.8893(3) 1.0215(5) 0.0782(17) Uani 1 1 d . . . C13 C 1.0267(6) 0.6574(3) 1.1005(5) 0.0733(15) Uani 1 1 d . . . C14 C 0.7271(4) 0.7912(3) 0.6800(4) 0.0572(11) Uani 1 1 d . . . C15 C 0.5929(5) 0.7089(2) 0.5196(4) 0.0583(12) Uani 1 1 d . . . H15 H 0.6322 0.6769 0.5694 0.070 Uiso 1 1 calc R . . C16 C 0.5587(5) 0.6757(3) 0.4124(5) 0.0721(15) Uani 1 1 d . . . H16A H 0.5606 0.7076 0.3554 0.086 Uiso 1 1 calc R . . H16B H 0.6165 0.6421 0.4015 0.086 Uiso 1 1 calc R . . C17 C 0.4377(5) 0.6454(3) 0.4056(5) 0.0758(16) Uani 1 1 d . . . H17A H 0.4343 0.6143 0.4636 0.091 Uiso 1 1 calc R . . H17B H 0.4223 0.6220 0.3383 0.091 Uiso 1 1 calc R . . C18 C 0.3446(4) 0.6974(2) 0.4127(4) 0.0575(12) Uani 1 1 d . . . H18 H 0.2668 0.6766 0.4115 0.069 Uiso 1 1 calc R . . C19 C 0.2991(4) 0.8006(2) 0.3470(4) 0.0510(10) Uani 1 1 d . . . H19 H 0.3279 0.8352 0.3023 0.061 Uiso 1 1 calc R . . C20 C 0.3440(4) 0.8122(2) 0.4655(3) 0.0475(10) Uani 1 1 d . . . H20 H 0.2860 0.8362 0.5030 0.057 Uiso 1 1 calc R . . C21 C 0.4658(4) 0.8448(2) 0.4801(4) 0.0543(11) Uani 1 1 d . . . H21A H 0.4582 0.8916 0.4891 0.065 Uiso 1 1 calc R . . H21B H 0.5091 0.8365 0.4187 0.065 Uiso 1 1 calc R . . C22 C 0.5284(4) 0.8135(2) 0.5816(4) 0.0503(10) Uani 1 1 d . . . H22 H 0.5078 0.8346 0.6473 0.060 Uiso 1 1 calc R . . C23 C 0.6613(4) 0.8100(2) 0.5762(3) 0.0525(10) Uani 1 1 d . . . H23 H 0.6911 0.8515 0.5507 0.063 Uiso 1 1 calc R . . C24 C 0.4891(5) 0.7418(2) 0.5738(4) 0.0495(10) Uani 1 1 d . . . H24 H 0.4851 0.7237 0.6457 0.059 Uiso 1 1 calc R . . C25 C 0.3640(4) 0.7426(2) 0.5109(4) 0.0506(11) Uani 1 1 d . . . H25 H 0.3046 0.7330 0.5601 0.061 Uiso 1 1 calc R . . C26 C 0.1676(5) 0.7972(3) 0.3305(4) 0.0613(12) Uani 1 1 d . . . F1 F 0.3880(7) -0.0593(3) 0.2490(8) 0.219(4) Uani 1 1 d . . . F2 F 0.2324(5) -0.0465(3) 0.3301(5) 0.153(2) Uani 1 1 d . . . F3 F 0.2104(6) 0.0059(8) 0.1815(6) 0.301(8) Uani 1 1 d . . . F4 F 0.2396(9) 0.0551(4) 0.3222(14) 0.311(7) Uani 1 1 d . . . F5 F 0.3988(8) 0.0154(9) 0.3504(13) 0.350(10) Uani 1 1 d . . . F7 F 0.3842(6) 0.0323(6) 0.1867(13) 0.337(9) Uani 1 1 d . . . N1 N 0.7783(4) 0.7720(3) 0.7556(4) 0.0689(12) Uani 1 1 d . . . N2 N 0.9098(5) 0.8450(3) 0.9869(5) 0.0941(18) Uani 1 1 d . . . N3 N 0.9588(5) 0.6762(3) 1.0347(4) 0.0945(18) Uani 1 1 d . . . N4 N 1.0692(5) 0.7102(3) 0.8174(5) 0.0872(15) Uani 1 1 d . . . O1 O 0.7939(3) 1.10062(19) 1.3584(3) 0.0744(10) Uani 1 1 d . . . O2 O 0.7376(3) 0.9282(2) 1.1437(4) 0.0780(12) Uani 1 1 d . . . O3 O 0.6755(3) 0.75987(17) 0.5022(3) 0.0588(9) Uani 1 1 d . . . O4 O 0.3457(3) 0.73962(16) 0.3195(3) 0.0594(9) Uani 1 1 d . . . P1 P 0.30847(17) -0.00268(10) 0.2625(2) 0.1085(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0625(3) 0.0559(3) 0.0556(3) 0.00301(15) -0.01189(19) 0.01099(16) C1 0.071(3) 0.051(3) 0.068(3) -0.012(2) 0.002(3) -0.002(2) C2 0.081(4) 0.075(3) 0.052(3) -0.008(2) 0.021(3) -0.006(3) C3 0.080(5) 0.094(5) 0.133(6) -0.008(4) 0.061(4) -0.013(4) C4 0.130(7) 0.090(5) 0.103(5) 0.009(4) 0.036(5) -0.047(5) C5 0.097(5) 0.050(3) 0.075(4) 0.004(2) 0.014(3) -0.019(3) C6 0.065(3) 0.058(3) 0.055(3) -0.011(2) 0.002(2) -0.008(2) C7 0.054(3) 0.049(2) 0.049(2) -0.0088(18) 0.010(2) -0.0070(19) C8 0.069(3) 0.042(2) 0.042(2) 0.0017(16) 0.006(2) -0.0073(19) C9 0.061(3) 0.048(2) 0.052(2) -0.0127(18) 0.014(2) -0.012(2) C10 0.047(3) 0.057(3) 0.051(2) -0.0016(19) -0.0038(19) 0.003(2) C11 0.058(3) 0.046(2) 0.065(3) 0.004(2) 0.004(2) 0.009(2) C12 0.084(4) 0.072(4) 0.081(4) -0.029(3) 0.018(3) -0.026(3) C13 0.084(4) 0.064(3) 0.072(3) 0.026(3) 0.009(3) 0.017(3) C14 0.049(3) 0.069(3) 0.051(3) -0.004(2) -0.004(2) 0.004(2) C15 0.063(3) 0.049(2) 0.061(3) -0.006(2) -0.003(2) 0.013(2) C16 0.052(3) 0.068(3) 0.094(4) -0.033(3) -0.001(3) 0.012(2) C17 0.072(4) 0.047(3) 0.106(5) -0.020(3) -0.005(3) 0.000(2) C18 0.044(3) 0.048(2) 0.080(3) -0.006(2) 0.003(2) -0.0088(19) C19 0.041(2) 0.055(2) 0.056(3) -0.003(2) 0.0002(19) -0.0018(19) C20 0.041(2) 0.047(2) 0.054(2) -0.0071(18) 0.0038(19) 0.0087(17) C21 0.052(3) 0.041(2) 0.066(3) 0.0017(19) -0.015(2) -0.0045(18) C22 0.052(3) 0.052(2) 0.047(2) -0.0041(18) 0.0008(19) 0.0060(19) C23 0.054(3) 0.060(3) 0.042(2) -0.0020(18) -0.0056(19) 0.003(2) C24 0.061(3) 0.048(2) 0.039(2) 0.0058(16) 0.003(2) 0.0041(19) C25 0.047(3) 0.053(2) 0.054(3) 0.0019(18) 0.018(2) -0.0023(18) C26 0.046(3) 0.066(3) 0.070(3) 0.002(2) -0.008(2) 0.000(2) F1 0.228(8) 0.124(5) 0.334(10) 0.033(6) 0.172(8) 0.001(5) F2 0.125(4) 0.145(5) 0.196(6) 0.028(4) 0.057(4) -0.014(3) F3 0.103(5) 0.68(2) 0.113(5) 0.084(8) -0.034(4) -0.044(8) F4 0.218(10) 0.133(6) 0.56(2) -0.043(9) -0.086(12) 0.054(6) F5 0.138(7) 0.49(2) 0.412(18) -0.245(18) -0.020(9) -0.020(10) F7 0.128(6) 0.329(12) 0.55(2) 0.344(15) 0.033(9) -0.024(7) N1 0.065(3) 0.085(3) 0.052(2) -0.001(2) -0.015(2) 0.013(2) N2 0.105(4) 0.066(3) 0.115(4) -0.043(3) 0.030(3) -0.013(3) N3 0.102(4) 0.098(4) 0.083(3) 0.041(3) 0.004(3) 0.038(3) N4 0.050(3) 0.098(4) 0.111(4) -0.008(3) -0.003(3) 0.006(3) O1 0.062(2) 0.070(2) 0.093(3) -0.030(2) 0.0185(19) -0.0063(18) O2 0.061(2) 0.077(3) 0.098(3) -0.024(2) 0.018(2) -0.0230(19) O3 0.049(2) 0.073(2) 0.0542(19) -0.0142(15) 0.0027(15) 0.0003(15) O4 0.054(2) 0.0620(19) 0.062(2) -0.0154(15) 0.0063(17) 0.0027(15) P1 0.0613(10) 0.0822(12) 0.175(2) 0.0650(13) -0.0216(12) -0.0100(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.200(4) . ? Ag1 N3 2.250(5) . ? Ag1 N2 2.292(5) . ? Ag1 N4 2.515(5) . ? C1 O1 1.385(6) . ? C1 C13 1.487(8) 2_757 ? C1 C9 1.511(6) . ? C1 H1 0.9800 . ? C2 O1 1.466(7) . ? C2 C3 1.520(9) . ? C2 C10 1.537(7) . ? C2 H2 0.9800 . ? C3 C4 1.460(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.475(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O2 1.453(7) . ? C5 C11 1.527(7) . ? C5 H5 0.9800 . ? C6 O2 1.415(6) . ? C6 C12 1.477(8) . ? C6 C7 1.524(6) . ? C6 H6 0.9800 . ? C7 C8 1.514(6) . ? C7 C11 1.544(6) . ? C7 H7 0.9800 . ? C8 C9 1.524(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.541(6) . ? C9 H9 0.9800 . ? C10 C11 1.552(6) . ? C10 H10 0.9800 . ? C11 H11 0.9800 . ? C12 N2 1.133(7) . ? C13 N3 1.136(7) . ? C13 C1 1.487(8) 2_747 ? C14 N1 1.130(6) . ? C14 C23 1.482(7) . ? C15 O3 1.434(6) . ? C15 C16 1.520(7) . ? C15 C24 1.572(7) . ? C15 H15 0.9800 . ? C16 C17 1.502(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.509(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 O4 1.456(6) . ? C18 C25 1.538(7) . ? C18 H18 0.9800 . ? C19 O4 1.413(5) . ? C19 C26 1.488(7) . ? C19 C20 1.539(6) . ? C19 H19 0.9800 . ? C20 C21 1.529(6) . ? C20 C25 1.541(6) . ? C20 H20 0.9800 . ? C21 C22 1.532(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.519(7) . ? C22 C24 1.534(6) . ? C22 H22 0.9800 . ? C23 O3 1.404(5) . ? C23 H23 0.9800 . ? C24 C25 1.551(7) . ? C24 H24 0.9800 . ? C25 H25 0.9800 . ? C26 N4 1.123(7) 4_475 ? F1 P1 1.490(7) . ? F2 P1 1.556(5) . ? F3 P1 1.438(6) . ? F4 P1 1.642(12) . ? F5 P1 1.473(10) . ? F7 P1 1.525(8) . ? N4 C26 1.123(7) 4_676 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 N3 154.1(2) . . ? N1 Ag1 N2 100.7(2) . . ? N3 Ag1 N2 102.4(2) . . ? N1 Ag1 N4 97.35(18) . . ? N3 Ag1 N4 83.9(2) . . ? N2 Ag1 N4 113.7(2) . . ? O1 C1 C13 110.2(5) . 2_757 ? O1 C1 C9 106.1(4) . . ? C13 C1 C9 109.8(5) 2_757 . ? O1 C1 H1 110.2 . . ? C13 C1 H1 110.2 2_757 . ? C9 C1 H1 110.2 . . ? O1 C2 C3 107.3(5) . . ? O1 C2 C10 105.8(4) . . ? C3 C2 C10 115.3(4) . . ? O1 C2 H2 109.4 . . ? C3 C2 H2 109.4 . . ? C10 C2 H2 109.4 . . ? C4 C3 C2 112.2(6) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 110.5(5) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O2 C5 C4 110.4(6) . . ? O2 C5 C11 106.6(4) . . ? C4 C5 C11 115.6(5) . . ? O2 C5 H5 108.0 . . ? C4 C5 H5 108.0 . . ? C11 C5 H5 108.0 . . ? O2 C6 C12 110.3(4) . . ? O2 C6 C7 105.4(4) . . ? C12 C6 C7 110.5(4) . . ? O2 C6 H6 110.2 . . ? C12 C6 H6 110.2 . . ? C7 C6 H6 110.2 . . ? C8 C7 C6 114.3(4) . . ? C8 C7 C11 105.5(3) . . ? C6 C7 C11 103.8(4) . . ? C8 C7 H7 110.9 . . ? C6 C7 H7 110.9 . . ? C11 C7 H7 110.9 . . ? C7 C8 C9 103.5(4) . . ? C7 C8 H8A 111.1 . . ? C9 C8 H8A 111.1 . . ? C7 C8 H8B 111.1 . . ? C9 C8 H8B 111.1 . . ? H8A C8 H8B 109.0 . . ? C1 C9 C8 114.0(4) . . ? C1 C9 C10 103.1(4) . . ? C8 C9 C10 104.4(3) . . ? C1 C9 H9 111.6 . . ? C8 C9 H9 111.6 . . ? C10 C9 H9 111.6 . . ? C2 C10 C9 103.9(4) . . ? C2 C10 C11 117.3(4) . . ? C9 C10 C11 104.9(4) . . ? C2 C10 H10 110.1 . . ? C9 C10 H10 110.1 . . ? C11 C10 H10 110.1 . . ? C5 C11 C7 104.4(4) . . ? C5 C11 C10 117.6(4) . . ? C7 C11 C10 106.2(4) . . ? C5 C11 H11 109.4 . . ? C7 C11 H11 109.4 . . ? C10 C11 H11 109.4 . . ? N2 C12 C6 178.2(7) . . ? N3 C13 C1 177.1(7) . 2_747 ? N1 C14 C23 174.4(6) . . ? O3 C15 C16 107.6(4) . . ? O3 C15 C24 106.6(3) . . ? C16 C15 C24 116.0(4) . . ? O3 C15 H15 108.8 . . ? C16 C15 H15 108.8 . . ? C24 C15 H15 108.8 . . ? C17 C16 C15 112.6(5) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C18 110.3(4) . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? C16 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? O4 C18 C17 107.9(4) . . ? O4 C18 C25 105.8(4) . . ? C17 C18 C25 115.4(4) . . ? O4 C18 H18 109.2 . . ? C17 C18 H18 109.2 . . ? C25 C18 H18 109.2 . . ? O4 C19 C26 108.7(4) . . ? O4 C19 C20 106.1(4) . . ? C26 C19 C20 111.6(4) . . ? O4 C19 H19 110.1 . . ? C26 C19 H19 110.1 . . ? C20 C19 H19 110.1 . . ? C21 C20 C19 112.8(4) . . ? C21 C20 C25 105.2(4) . . ? C19 C20 C25 103.6(3) . . ? C21 C20 H20 111.6 . . ? C19 C20 H20 111.6 . . ? C25 C20 H20 111.6 . . ? C20 C21 C22 104.6(4) . . ? C20 C21 H21A 110.8 . . ? C22 C21 H21A 110.8 . . ? C20 C21 H21B 110.8 . . ? C22 C21 H21B 110.8 . . ? H21A C21 H21B 108.9 . . ? C23 C22 C21 111.1(4) . . ? C23 C22 C24 103.6(4) . . ? C21 C22 C24 103.9(4) . . ? C23 C22 H22 112.5 . . ? C21 C22 H22 112.5 . . ? C24 C22 H22 112.5 . . ? O3 C23 C14 108.0(4) . . ? O3 C23 C22 104.2(4) . . ? C14 C23 C22 112.7(4) . . ? O3 C23 H23 110.6 . . ? C14 C23 H23 110.6 . . ? C22 C23 H23 110.6 . . ? C22 C24 C25 105.5(3) . . ? C22 C24 C15 102.2(4) . . ? C25 C24 C15 118.2(4) . . ? C22 C24 H24 110.1 . . ? C25 C24 H24 110.1 . . ? C15 C24 H24 110.1 . . ? C18 C25 C20 104.9(4) . . ? C18 C25 C24 116.6(4) . . ? C20 C25 C24 106.8(4) . . ? C18 C25 H25 109.4 . . ? C20 C25 H25 109.4 . . ? C24 C25 H25 109.4 . . ? N4 C26 C19 174.9(6) 4_475 . ? C14 N1 Ag1 173.4(5) . . ? C12 N2 Ag1 149.3(5) . . ? C13 N3 Ag1 154.7(6) . . ? C26 N4 Ag1 144.8(5) 4_676 . ? C1 O1 C2 110.1(4) . . ? C6 O2 C5 107.4(4) . . ? C23 O3 C15 108.1(4) . . ? C19 O4 C18 107.1(4) . . ? F3 P1 F5 157.8(10) . . ? F3 P1 F1 116.7(8) . . ? F5 P1 F1 84.1(7) . . ? F3 P1 F7 87.0(5) . . ? F5 P1 F7 87.4(8) . . ? F1 P1 F7 84.6(5) . . ? F3 P1 F2 91.3(5) . . ? F5 P1 F2 96.8(8) . . ? F1 P1 F2 89.5(3) . . ? F7 P1 F2 172.3(7) . . ? F3 P1 F4 82.1(7) . . ? F5 P1 F4 78.8(6) . . ? F1 P1 F4 159.3(7) . . ? F7 P1 F4 105.8(8) . . ? F2 P1 F4 81.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 159.8(5) . . . . ? C10 C2 C3 C4 42.2(8) . . . . ? C2 C3 C4 C5 -66.3(9) . . . . ? C3 C4 C5 O2 -69.7(8) . . . . ? C3 C4 C5 C11 51.4(9) . . . . ? O2 C6 C7 C8 -84.3(5) . . . . ? C12 C6 C7 C8 156.6(4) . . . . ? O2 C6 C7 C11 30.1(5) . . . . ? C12 C6 C7 C11 -89.0(5) . . . . ? C6 C7 C8 C9 148.5(4) . . . . ? C11 C7 C8 C9 35.1(5) . . . . ? O1 C1 C9 C8 78.8(5) . . . . ? C13 C1 C9 C8 -162.2(4) 2_757 . . . ? O1 C1 C9 C10 -33.7(5) . . . . ? C13 C1 C9 C10 85.3(5) 2_757 . . . ? C7 C8 C9 C1 -151.5(4) . . . . ? C7 C8 C9 C10 -39.8(5) . . . . ? O1 C2 C10 C9 -8.1(5) . . . . ? C3 C2 C10 C9 110.3(6) . . . . ? O1 C2 C10 C11 -123.2(4) . . . . ? C3 C2 C10 C11 -4.8(7) . . . . ? C1 C9 C10 C2 24.5(5) . . . . ? C8 C9 C10 C2 -94.8(4) . . . . ? C1 C9 C10 C11 148.2(4) . . . . ? C8 C9 C10 C11 28.8(5) . . . . ? O2 C5 C11 C7 -8.2(5) . . . . ? C4 C5 C11 C7 -131.2(6) . . . . ? O2 C5 C11 C10 109.2(5) . . . . ? C4 C5 C11 C10 -13.9(8) . . . . ? C8 C7 C11 C5 107.8(4) . . . . ? C6 C7 C11 C5 -12.7(5) . . . . ? C8 C7 C11 C10 -17.1(5) . . . . ? C6 C7 C11 C10 -137.7(4) . . . . ? C2 C10 C11 C5 -9.1(6) . . . . ? C9 C10 C11 C5 -123.7(5) . . . . ? C2 C10 C11 C7 107.3(5) . . . . ? C9 C10 C11 C7 -7.2(5) . . . . ? O2 C6 C12 N2 -100(22) . . . . ? C7 C6 C12 N2 16(22) . . . . ? O3 C15 C16 C17 -153.0(5) . . . . ? C24 C15 C16 C17 -33.8(7) . . . . ? C15 C16 C17 C18 63.6(7) . . . . ? C16 C17 C18 O4 64.1(6) . . . . ? C16 C17 C18 C25 -54.0(7) . . . . ? O4 C19 C20 C21 86.8(4) . . . . ? C26 C19 C20 C21 -155.0(4) . . . . ? O4 C19 C20 C25 -26.4(4) . . . . ? C26 C19 C20 C25 91.8(4) . . . . ? C19 C20 C21 C22 -143.7(4) . . . . ? C25 C20 C21 C22 -31.4(5) . . . . ? C20 C21 C22 C23 149.0(4) . . . . ? C20 C21 C22 C24 38.1(5) . . . . ? N1 C14 C23 O3 -10(6) . . . . ? N1 C14 C23 C22 105(6) . . . . ? C21 C22 C23 O3 -73.5(4) . . . . ? C24 C22 C23 O3 37.5(4) . . . . ? C21 C22 C23 C14 169.7(4) . . . . ? C24 C22 C23 C14 -79.3(4) . . . . ? C23 C22 C24 C25 -146.0(4) . . . . ? C21 C22 C24 C25 -29.8(5) . . . . ? C23 C22 C24 C15 -21.8(4) . . . . ? C21 C22 C24 C15 94.5(4) . . . . ? O3 C15 C24 C22 -0.1(5) . . . . ? C16 C15 C24 C22 -119.9(5) . . . . ? O3 C15 C24 C25 115.1(4) . . . . ? C16 C15 C24 C25 -4.7(6) . . . . ? O4 C18 C25 C20 13.9(5) . . . . ? C17 C18 C25 C20 133.1(5) . . . . ? O4 C18 C25 C24 -104.0(4) . . . . ? C17 C18 C25 C24 15.1(6) . . . . ? C21 C20 C25 C18 -111.6(4) . . . . ? C19 C20 C25 C18 7.0(5) . . . . ? C21 C20 C25 C24 12.8(5) . . . . ? C19 C20 C25 C24 131.4(4) . . . . ? C22 C24 C25 C18 127.5(4) . . . . ? C15 C24 C25 C18 14.1(6) . . . . ? C22 C24 C25 C20 10.6(5) . . . . ? C15 C24 C25 C20 -102.9(4) . . . . ? O4 C19 C26 N4 12(7) . . . 4_475 ? C20 C19 C26 N4 -104(7) . . . 4_475 ? C23 C14 N1 Ag1 137(5) . . . . ? N3 Ag1 N1 C14 -172(4) . . . . ? N2 Ag1 N1 C14 35(4) . . . . ? N4 Ag1 N1 C14 -81(4) . . . . ? C6 C12 N2 Ag1 152(21) . . . . ? N1 Ag1 N2 C12 58.4(12) . . . . ? N3 Ag1 N2 C12 -109.9(12) . . . . ? N4 Ag1 N2 C12 161.4(11) . . . . ? C1 C13 N3 Ag1 -162(12) 2_747 . . . ? N1 Ag1 N3 C13 154.8(11) . . . . ? N2 Ag1 N3 C13 -52.4(13) . . . . ? N4 Ag1 N3 C13 60.5(13) . . . . ? N1 Ag1 N4 C26 156.8(9) . . . 4_676 ? N3 Ag1 N4 C26 -49.3(9) . . . 4_676 ? N2 Ag1 N4 C26 51.6(9) . . . 4_676 ? C13 C1 O1 C2 -88.8(5) 2_757 . . . ? C9 C1 O1 C2 30.0(6) . . . . ? C3 C2 O1 C1 -137.1(5) . . . . ? C10 C2 O1 C1 -13.5(5) . . . . ? C12 C6 O2 C5 82.6(5) . . . . ? C7 C6 O2 C5 -36.6(5) . . . . ? C4 C5 O2 C6 154.4(5) . . . . ? C11 C5 O2 C6 28.1(5) . . . . ? C14 C23 O3 C15 81.1(5) . . . . ? C22 C23 O3 C15 -38.9(5) . . . . ? C16 C15 O3 C23 149.5(4) . . . . ? C24 C15 O3 C23 24.4(5) . . . . ? C26 C19 O4 C18 -83.5(4) . . . . ? C20 C19 O4 C18 36.7(5) . . . . ? C17 C18 O4 C19 -155.8(4) . . . . ? C25 C18 O4 C19 -31.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.310 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 942148' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C17 H14 Ag F6 N2 O2 Sb), 2(C0.50 H2 O0.50)' _chemical_formula_sum ' C35 H32 Ag2 F12 N4 O5 Sb2' _chemical_formula_weight 1275.91 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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' 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 P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4347(4) _cell_length_b 18.1183(10) _cell_length_c 15.1884(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.864(3) _cell_angle_gamma 90.00 _cell_volume 2035.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7253 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 29.93 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 2.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4919 _exptl_absorpt_correction_T_max 0.6758 _exptl_absorpt_process_details 'SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXIICCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12463 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3550 _reflns_number_gt 3116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII, Bruker,2004' _computing_cell_refinement 'APEXII/SAINT, Bruker,2004' _computing_data_reduction 'SAINT PLUS/XPREP, Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0480P)^2^+7.4449P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3550 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ag1 Ag -0.45695(5) 0.20521(3) -0.00562(3) 0.05551(17) Uani 1 1 d . . . C1 C 0.5717(6) 0.3944(3) 0.0561(3) 0.0361(11) Uani 1 1 d . . . C2 C 0.7237(8) 0.4189(3) 0.0174(4) 0.0470(13) Uani 1 1 d . . . H2 H 0.8270 0.4329 0.0533 0.056 Uiso 1 1 calc R . . C3 C 0.7221(9) 0.4227(3) -0.0734(4) 0.0537(15) Uani 1 1 d . . . H3 H 0.8254 0.4372 -0.0986 0.064 Uiso 1 1 calc R . . C4 C 0.5660(10) 0.4047(3) -0.1269(4) 0.0562(16) Uani 1 1 d . . . H4 H 0.5642 0.4079 -0.1881 0.067 Uiso 1 1 calc R . . C5 C 0.4126(9) 0.3818(3) -0.0896(4) 0.0492(13) Uani 1 1 d . . . H5 H 0.3077 0.3705 -0.1259 0.059 Uiso 1 1 calc R . . C6 C 0.4152(7) 0.3758(3) 0.0022(3) 0.0352(11) Uani 1 1 d . . . C7 C 0.2530(6) 0.3492(3) 0.0430(3) 0.0360(11) Uani 1 1 d . . . H7 H 0.1446 0.3585 0.0022 0.043 Uiso 1 1 calc R . . C8 C 0.1446(6) 0.2499(3) 0.1167(3) 0.0360(11) Uani 1 1 d . . . H8 H 0.1870 0.2065 0.1514 0.043 Uiso 1 1 calc R . . C9 C 0.1264(6) 0.3172(3) 0.1793(3) 0.0367(11) Uani 1 1 d . . . H9 H -0.0012 0.3297 0.1816 0.044 Uiso 1 1 calc R . . C10 C 0.2216(7) 0.3084(3) 0.2731(4) 0.0452(13) Uani 1 1 d . . . H10A H 0.1531 0.3330 0.3156 0.054 Uiso 1 1 calc R . . H10B H 0.2329 0.2566 0.2887 0.054 Uiso 1 1 calc R . . C11 C 0.4087(6) 0.3436(3) 0.2731(3) 0.0365(11) Uani 1 1 d . . . H11 H 0.4407 0.3701 0.3288 0.044 Uiso 1 1 calc R . . C12 C 0.5629(7) 0.2890(3) 0.2550(3) 0.0366(11) Uani 1 1 d . . . H12 H 0.5168 0.2384 0.2545 0.044 Uiso 1 1 calc R . . C13 C 0.5774(6) 0.3841(3) 0.1541(3) 0.0368(11) Uani 1 1 d . . . H13 H 0.6733 0.4149 0.1840 0.044 Uiso 1 1 calc R . . C14 C 0.4003(6) 0.3975(3) 0.1951(3) 0.0333(10) Uani 1 1 d . . . H14 H 0.3963 0.4484 0.2166 0.040 Uiso 1 1 calc R . . C15 C 0.2245(6) 0.3797(3) 0.1342(3) 0.0346(10) Uani 1 1 d . . . H15 H 0.1471 0.4236 0.1279 0.041 Uiso 1 1 calc R . . F1 F -0.6328(9) 0.1132(4) 0.2193(5) 0.155(3) Uani 1 1 d . . . F2 F -0.2887(7) 0.1191(3) 0.2029(3) 0.1057(17) Uani 1 1 d . . . F3 F -0.4290(7) 0.0144(3) 0.2979(3) 0.1002(16) Uani 1 1 d . . . F4 F -0.2795(11) -0.0165(4) 0.1597(5) 0.153(3) Uani 1 1 d . . . F5 F -0.6460(12) -0.0228(5) 0.1644(5) 0.194(4) Uani 1 1 d . . . F6 F -0.5120(10) 0.0827(4) 0.0639(4) 0.155(3) Uani 1 1 d . . . C21 C -0.0332(7) 0.2335(3) 0.0650(4) 0.0408(12) Uani 1 1 d . . . C20 C 0.7181(7) 0.2961(3) 0.3242(4) 0.0400(12) Uani 1 1 d . . . N5 N -0.6642(6) 0.1989(3) -0.1223(3) 0.0504(12) Uani 1 1 d . . . N4 N -0.1690(6) 0.2222(3) 0.0276(3) 0.0495(12) Uani 1 1 d . . . O1 O 0.2722(4) 0.26955(18) 0.0580(2) 0.0367(8) Uani 1 1 d . . . O2 O 0.6186(5) 0.3060(2) 0.1719(2) 0.0420(8) Uani 1 1 d . . . C17 C -0.0055(15) 0.0400(5) 0.0103(9) 0.040(2) Uani 0.50 1 d P A -1 H17A H -0.0076 0.0450 0.0732 0.060 Uiso 0.50 1 calc PR A -1 H17B H -0.0010 -0.0114 -0.0048 0.060 Uiso 0.50 1 calc PR A -1 H17C H -0.1127 0.0618 -0.0195 0.060 Uiso 0.50 1 calc PR A -1 O4 O 0.1248(16) 0.0707(6) -0.0120(8) 0.082(3) Uani 0.50 1 d P A -1 H4A H 0.1900 0.0406 -0.0336 0.122 Uiso 0.50 1 calc PR A -1 Sb1 Sb -0.47036(6) 0.04777(2) 0.18059(3) 0.04889(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0299(2) 0.0817(4) 0.0535(3) -0.0012(2) -0.00274(19) -0.0058(2) C1 0.033(2) 0.037(3) 0.039(3) 0.002(2) 0.007(2) 0.001(2) C2 0.045(3) 0.045(3) 0.052(3) 0.005(3) 0.010(3) -0.006(2) C3 0.068(4) 0.043(3) 0.055(4) 0.007(3) 0.028(3) -0.005(3) C4 0.088(5) 0.045(3) 0.039(3) 0.010(3) 0.023(3) -0.002(3) C5 0.062(4) 0.048(3) 0.037(3) 0.005(2) 0.001(3) -0.003(3) C6 0.040(3) 0.035(3) 0.031(3) 0.003(2) 0.005(2) 0.003(2) C7 0.033(2) 0.042(3) 0.032(3) 0.002(2) -0.004(2) 0.004(2) C8 0.029(2) 0.040(3) 0.039(3) -0.001(2) 0.003(2) -0.003(2) C9 0.023(2) 0.048(3) 0.039(3) -0.003(2) 0.007(2) 0.001(2) C10 0.036(3) 0.065(4) 0.035(3) -0.005(3) 0.010(2) -0.003(2) C11 0.033(2) 0.048(3) 0.029(3) -0.007(2) 0.003(2) 0.000(2) C12 0.034(3) 0.043(3) 0.033(3) 0.002(2) 0.003(2) 0.002(2) C13 0.026(2) 0.049(3) 0.035(3) -0.003(2) 0.0017(19) -0.003(2) C14 0.030(2) 0.034(2) 0.036(3) -0.009(2) 0.001(2) 0.0022(19) C15 0.027(2) 0.037(3) 0.039(3) -0.001(2) -0.0010(19) 0.0075(19) F1 0.156(6) 0.136(5) 0.190(7) 0.064(5) 0.102(5) 0.095(5) F2 0.107(4) 0.117(4) 0.087(3) 0.023(3) -0.016(3) -0.042(3) F3 0.091(3) 0.133(4) 0.078(3) 0.054(3) 0.014(2) 0.023(3) F4 0.201(7) 0.118(5) 0.159(6) 0.026(4) 0.110(6) 0.067(5) F5 0.230(8) 0.186(7) 0.149(6) 0.078(5) -0.057(6) -0.155(7) F6 0.196(7) 0.175(6) 0.084(4) 0.061(4) -0.036(4) -0.098(6) C21 0.037(3) 0.040(3) 0.046(3) -0.003(2) 0.009(2) -0.003(2) C20 0.035(3) 0.049(3) 0.036(3) 0.012(2) 0.007(2) 0.002(2) N5 0.040(3) 0.072(3) 0.038(3) -0.015(2) -0.001(2) 0.001(2) N4 0.032(2) 0.057(3) 0.058(3) -0.012(2) -0.001(2) -0.006(2) O1 0.0328(17) 0.0374(18) 0.041(2) -0.0068(15) 0.0093(14) -0.0035(14) O2 0.0400(19) 0.056(2) 0.0309(19) 0.0021(16) 0.0057(15) 0.0186(17) C17 0.030(5) 0.027(5) 0.064(7) -0.007(5) 0.014(5) 0.000(4) O4 0.096(8) 0.073(6) 0.074(7) -0.002(6) -0.001(6) 0.019(6) Sb1 0.0601(3) 0.0433(2) 0.0445(2) 0.00885(16) 0.01122(18) 0.00338(17) _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 2.171(5) . ? Ag1 N5 2.229(5) . ? Ag1 F6 2.510(6) . ? Ag1 O1 2.597(3) 1_455 ? C1 C6 1.394(7) . ? C1 C2 1.399(7) . ? C1 C13 1.495(7) . ? C2 C3 1.380(8) . ? C2 H2 0.9300 . ? C3 C4 1.386(9) . ? C3 H3 0.9300 . ? C4 C5 1.387(8) . ? C4 H4 0.9300 . ? C5 C6 1.398(7) . ? C5 H5 0.9300 . ? C6 C7 1.491(7) . ? C7 O1 1.465(6) . ? C7 C15 1.527(7) . ? C7 H7 0.9800 . ? C8 O1 1.412(6) . ? C8 C21 1.496(7) . ? C8 C9 1.561(7) . ? C8 H8 0.9800 . ? C9 C10 1.532(7) . ? C9 C15 1.545(7) . ? C9 H9 0.9800 . ? C10 C11 1.530(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C14 1.532(7) . ? C11 C12 1.560(7) . ? C11 H11 0.9800 . ? C12 O2 1.403(6) . ? C12 C20 1.485(7) . ? C12 H12 0.9800 . ? C13 O2 1.466(6) . ? C13 C14 1.533(6) . ? C13 H13 0.9800 . ? C14 C15 1.555(6) . ? C14 H14 0.9800 . ? C15 H15 0.9800 . ? F1 Sb1 1.831(5) . ? F2 Sb1 1.875(5) . ? F3 Sb1 1.877(4) . ? F4 Sb1 1.887(6) . ? F5 Sb1 1.826(6) . ? F6 Sb1 1.878(5) . ? C21 N4 1.125(7) . ? C20 N5 1.136(7) 4_766 ? N5 C20 1.136(7) 4_465 ? O1 Ag1 2.597(3) 1_655 ? C17 O4 1.196(15) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O4 H4A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ag1 N5 141.02(19) . . ? N4 Ag1 F6 103.1(2) . . ? N5 Ag1 F6 99.18(19) . . ? N4 Ag1 O1 129.30(15) . 1_455 ? N5 Ag1 O1 79.60(14) . 1_455 ? F6 Ag1 O1 94.3(2) . 1_455 ? C6 C1 C2 119.4(5) . . ? C6 C1 C13 119.4(4) . . ? C2 C1 C13 121.1(5) . . ? C3 C2 C1 120.7(5) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.7(5) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.3(5) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.1(6) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 119.6(5) . . ? C1 C6 C7 119.7(4) . . ? C5 C6 C7 120.7(5) . . ? O1 C7 C6 108.3(4) . . ? O1 C7 C15 103.7(4) . . ? C6 C7 C15 116.9(4) . . ? O1 C7 H7 109.2 . . ? C6 C7 H7 109.2 . . ? C15 C7 H7 109.2 . . ? O1 C8 C21 109.4(4) . . ? O1 C8 C9 107.0(4) . . ? C21 C8 C9 110.3(4) . . ? O1 C8 H8 110.0 . . ? C21 C8 H8 110.0 . . ? C9 C8 H8 110.0 . . ? C10 C9 C15 107.1(4) . . ? C10 C9 C8 115.2(4) . . ? C15 C9 C8 103.2(4) . . ? C10 C9 H9 110.4 . . ? C15 C9 H9 110.4 . . ? C8 C9 H9 110.4 . . ? C11 C10 C9 106.9(4) . . ? C11 C10 H10A 110.3 . . ? C9 C10 H10A 110.3 . . ? C11 C10 H10B 110.3 . . ? C9 C10 H10B 110.3 . . ? H10A C10 H10B 108.6 . . ? C10 C11 C14 107.5(4) . . ? C10 C11 C12 114.8(4) . . ? C14 C11 C12 103.9(4) . . ? C10 C11 H11 110.1 . . ? C14 C11 H11 110.1 . . ? C12 C11 H11 110.1 . . ? O2 C12 C20 109.8(4) . . ? O2 C12 C11 108.0(4) . . ? C20 C12 C11 110.6(4) . . ? O2 C12 H12 109.5 . . ? C20 C12 H12 109.5 . . ? C11 C12 H12 109.5 . . ? O2 C13 C1 106.7(4) . . ? O2 C13 C14 104.5(4) . . ? C1 C13 C14 116.5(4) . . ? O2 C13 H13 109.6 . . ? C1 C13 H13 109.6 . . ? C14 C13 H13 109.6 . . ? C11 C14 C13 104.1(4) . . ? C11 C14 C15 107.0(4) . . ? C13 C14 C15 115.5(4) . . ? C11 C14 H14 110.0 . . ? C13 C14 H14 110.0 . . ? C15 C14 H14 110.0 . . ? C7 C15 C9 104.6(4) . . ? C7 C15 C14 115.3(4) . . ? C9 C15 C14 107.2(4) . . ? C7 C15 H15 109.8 . . ? C9 C15 H15 109.8 . . ? C14 C15 H15 109.8 . . ? Sb1 F6 Ag1 132.6(3) . . ? N4 C21 C8 178.2(6) . . ? N5 C20 C12 179.2(6) 4_766 . ? C20 N5 Ag1 169.9(4) 4_465 . ? C21 N4 Ag1 162.9(5) . . ? C8 O1 C7 106.6(4) . . ? C8 O1 Ag1 135.9(3) . 1_655 ? C7 O1 Ag1 116.8(3) . 1_655 ? C12 O2 C13 107.6(4) . . ? F5 Sb1 F1 90.6(5) . . ? F5 Sb1 F2 177.3(3) . . ? F1 Sb1 F2 89.0(3) . . ? F5 Sb1 F3 87.0(3) . . ? F1 Sb1 F3 87.4(3) . . ? F2 Sb1 F3 90.3(2) . . ? F5 Sb1 F6 93.6(3) . . ? F1 Sb1 F6 92.0(4) . . ? F2 Sb1 F6 89.1(2) . . ? F3 Sb1 F6 179.1(3) . . ? F5 Sb1 F4 94.8(4) . . ? F1 Sb1 F4 170.1(4) . . ? F2 Sb1 F4 85.2(3) . . ? F3 Sb1 F4 84.7(3) . . ? F6 Sb1 F4 95.9(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.1(8) . . . . ? C13 C1 C2 C3 174.7(5) . . . . ? C1 C2 C3 C4 2.5(9) . . . . ? C2 C3 C4 C5 -1.0(9) . . . . ? C3 C4 C5 C6 -1.0(9) . . . . ? C2 C1 C6 C5 0.1(8) . . . . ? C13 C1 C6 C5 -176.7(5) . . . . ? C2 C1 C6 C7 179.6(5) . . . . ? C13 C1 C6 C7 2.8(7) . . . . ? C4 C5 C6 C1 1.4(8) . . . . ? C4 C5 C6 C7 -178.1(5) . . . . ? C1 C6 C7 O1 -85.1(5) . . . . ? C5 C6 C7 O1 94.4(5) . . . . ? C1 C6 C7 C15 31.5(6) . . . . ? C5 C6 C7 C15 -149.0(5) . . . . ? O1 C8 C9 C10 -104.2(5) . . . . ? C21 C8 C9 C10 136.8(4) . . . . ? O1 C8 C9 C15 12.1(5) . . . . ? C21 C8 C9 C15 -106.9(4) . . . . ? C15 C9 C10 C11 -19.7(5) . . . . ? C8 C9 C10 C11 94.4(5) . . . . ? C9 C10 C11 C14 21.2(6) . . . . ? C9 C10 C11 C12 -93.8(5) . . . . ? C10 C11 C12 O2 111.3(5) . . . . ? C14 C11 C12 O2 -5.8(5) . . . . ? C10 C11 C12 C20 -128.5(5) . . . . ? C14 C11 C12 C20 114.4(4) . . . . ? C6 C1 C13 O2 81.7(5) . . . . ? C2 C1 C13 O2 -95.1(5) . . . . ? C6 C1 C13 C14 -34.5(7) . . . . ? C2 C1 C13 C14 148.7(5) . . . . ? C10 C11 C14 C13 -137.2(4) . . . . ? C12 C11 C14 C13 -15.1(5) . . . . ? C10 C11 C14 C15 -14.5(5) . . . . ? C12 C11 C14 C15 107.6(4) . . . . ? O2 C13 C14 C11 30.4(5) . . . . ? C1 C13 C14 C11 147.9(4) . . . . ? O2 C13 C14 C15 -86.6(5) . . . . ? C1 C13 C14 C15 30.9(6) . . . . ? O1 C7 C15 C9 -30.8(4) . . . . ? C6 C7 C15 C9 -149.8(4) . . . . ? O1 C7 C15 C14 86.6(5) . . . . ? C6 C7 C15 C14 -32.4(6) . . . . ? C10 C9 C15 C7 133.6(4) . . . . ? C8 C9 C15 C7 11.7(5) . . . . ? C10 C9 C15 C14 10.7(5) . . . . ? C8 C9 C15 C14 -111.2(4) . . . . ? C11 C14 C15 C7 -113.7(4) . . . . ? C13 C14 C15 C7 1.7(6) . . . . ? C11 C14 C15 C9 2.3(5) . . . . ? C13 C14 C15 C9 117.7(4) . . . . ? N4 Ag1 F6 Sb1 57.1(6) . . . . ? N5 Ag1 F6 Sb1 -155.0(5) . . . . ? O1 Ag1 F6 Sb1 -74.9(6) 1_455 . . . ? O1 C8 C21 N4 -137(21) . . . . ? C9 C8 C21 N4 -19(21) . . . . ? O2 C12 C20 N5 -162(100) . . . 4_766 ? C11 C12 C20 N5 79(54) . . . 4_766 ? N4 Ag1 N5 C20 -123(3) . . . 4_465 ? F6 Ag1 N5 C20 113(3) . . . 4_465 ? O1 Ag1 N5 C20 20(3) 1_455 . . 4_465 ? C8 C21 N4 Ag1 -26(22) . . . . ? N5 Ag1 N4 C21 165.4(15) . . . . ? F6 Ag1 N4 C21 -71.3(16) . . . . ? O1 Ag1 N4 C21 35.6(17) 1_455 . . . ? C21 C8 O1 C7 86.9(5) . . . . ? C9 C8 O1 C7 -32.7(5) . . . . ? C21 C8 O1 Ag1 -103.5(4) . . . 1_655 ? C9 C8 O1 Ag1 136.9(3) . . . 1_655 ? C6 C7 O1 C8 164.8(4) . . . . ? C15 C7 O1 C8 40.0(4) . . . . ? C6 C7 O1 Ag1 -7.0(4) . . . 1_655 ? C15 C7 O1 Ag1 -131.9(3) . . . 1_655 ? C20 C12 O2 C13 -94.9(5) . . . . ? C11 C12 O2 C13 25.8(5) . . . . ? C1 C13 O2 C12 -159.4(4) . . . . ? C14 C13 O2 C12 -35.5(5) . . . . ? Ag1 F6 Sb1 F5 155.0(6) . . . . ? Ag1 F6 Sb1 F1 64.3(6) . . . . ? Ag1 F6 Sb1 F2 -24.7(6) . . . . ? Ag1 F6 Sb1 F3 26(18) . . . . ? Ag1 F6 Sb1 F4 -109.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.995 _refine_diff_density_min -0.913 _refine_diff_density_rms 0.112 _vrf_PLAT241_new ; PROBLEM: Check High Ueq as Compared to Neighbors for F6 RESPONSE: This alarm is due to the elongated ADPs of Fluorine atoms which suggest that these are probably disordered. ; _vrf_PLAT312_new ; PROBLEM: Strange C-O-H Geometry (C-O < 1.25 Ang) ..... O4 RESPONSE: This alarm is due to the disordered Carbon and oxygen atoms which suggest that these are in two orientations. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 942149' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 Ag N2 O3, F6 P' _chemical_formula_sum 'C17 H16 Ag F6 N2 O3 P' _chemical_formula_weight 549.16 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmna _symmetry_space_group_name_Hall '-P 2ac 2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y, -z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y, z' 'x-1/2, -y, z-1/2' _cell_length_a 13.5994(5) _cell_length_b 9.9972(5) _cell_length_c 14.0444(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1909.42(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4715 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 28.21 _exptl_crystal_description Block _exptl_crystal_colour white _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7503 _exptl_absorpt_correction_T_max 0.8382 _exptl_absorpt_process_details ' SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7551 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.46 _reflns_number_total 2348 _reflns_number_gt 1986 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0968P)^2^+3.3693P] 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 ? _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 2348 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1744 _refine_ls_wR_factor_gt 0.1682 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.005 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 Ag01 Ag 0.5000 0.33364(6) 0.93987(4) 0.0597(3) Uani 1 2 d S . . P1 P 0.2500 0.61670(17) 0.7500 0.0483(4) Uani 1 2 d S . . O1 O 0.14475(19) 0.1017(2) 0.90950(19) 0.0353(6) Uani 1 1 d . . . C4 C 0.1093(2) 0.1892(3) 0.8342(2) 0.0295(7) Uani 1 1 d . . . H4 H 0.1664 0.2255 0.8002 0.035 Uiso 1 1 calc R . . O2 O 0.5000 0.5665(6) 0.8855(4) 0.0632(13) Uani 1 2 d S . . C3 C 0.0566(2) 0.3052(3) 0.8841(2) 0.0284(7) Uani 1 1 d . . . H3 H 0.0806 0.3903 0.8584 0.034 Uiso 1 1 calc R . . F3 F 0.1355(3) 0.6135(5) 0.7711(3) 0.0975(13) Uani 1 1 d . . . C6 C 0.0514(2) 0.1048(3) 0.7659(2) 0.0309(7) Uani 1 1 d . . . C1 C 0.1709(3) 0.1876(3) 0.9857(3) 0.0340(7) Uani 1 1 d . . . H1 H 0.1726 0.1367 1.0453 0.041 Uiso 1 1 calc R . . C7 C 0.1011(3) 0.0231(5) 0.7027(3) 0.0488(10) Uani 1 1 d . . . H7 H 0.1695 0.0233 0.7021 0.059 Uiso 1 1 calc R . . C9 C 0.0000 0.2358(6) 1.0422(4) 0.0401(11) Uani 1 2 d S . . H9A H 0.0000 0.1388 1.0405 0.048 Uiso 1 2 calc SR . . H9B H 0.0000 0.2646 1.1082 0.048 Uiso 1 2 calc SR . . N1 N 0.3464(3) 0.2818(4) 0.9490(3) 0.0497(9) Uani 1 1 d . . . C10 C 0.2697(3) 0.2446(4) 0.9661(3) 0.0389(8) Uani 1 1 d . . . C2 C 0.0899(2) 0.2912(3) 0.9901(3) 0.0332(7) Uani 1 1 d . . . H2 H 0.1126 0.3763 1.0170 0.040 Uiso 1 1 calc R . . C8 C 0.0505(4) -0.0590(5) 0.6401(4) 0.0612(13) Uani 1 1 d . . . H8 H 0.0848 -0.1139 0.5982 0.073 Uiso 1 1 calc R . . F1 F 0.2632(5) 0.5119(10) 0.8214(8) 0.303(8) Uani 1 1 d . . . F2 F 0.2644(5) 0.7147(12) 0.8253(6) 0.246(6) Uani 1 1 d . . . H1O H 0.454(4) 0.580(6) 0.856(4) 0.055(15) 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 Ag01 0.0238(3) 0.0797(4) 0.0757(5) 0.0065(3) 0.000 0.000 P1 0.0419(9) 0.0535(8) 0.0496(8) 0.000 -0.0020(6) 0.000 O1 0.0312(13) 0.0307(11) 0.0439(14) -0.0021(10) -0.0097(11) 0.0041(9) C4 0.0185(15) 0.0359(15) 0.0341(16) 0.0020(12) 0.0002(12) -0.0008(11) O2 0.052(3) 0.076(3) 0.062(3) 0.015(3) 0.000 0.000 C3 0.0224(16) 0.0260(13) 0.0369(17) 0.0041(12) -0.0005(12) -0.0030(10) F3 0.0474(19) 0.143(4) 0.102(3) 0.000(3) 0.0048(19) -0.001(2) C6 0.0257(17) 0.0372(15) 0.0299(16) 0.0000(12) -0.0007(12) 0.0003(12) C1 0.0255(16) 0.0402(16) 0.0364(18) 0.0011(13) -0.0054(14) -0.0003(13) C7 0.0307(18) 0.068(3) 0.047(2) -0.0153(19) 0.0057(17) 0.0044(18) C9 0.030(3) 0.057(3) 0.033(2) -0.001(2) 0.000 0.000 N1 0.0231(17) 0.066(2) 0.060(2) -0.0017(17) -0.0045(14) -0.0029(15) C10 0.0253(18) 0.0447(18) 0.047(2) -0.0023(16) -0.0093(15) 0.0037(14) C2 0.0239(16) 0.0368(15) 0.0389(18) -0.0088(13) -0.0047(13) -0.0009(12) C8 0.053(3) 0.076(3) 0.054(3) -0.031(2) 0.007(2) 0.002(2) F1 0.115(5) 0.312(11) 0.483(19) 0.332(13) -0.018(8) -0.006(7) F2 0.136(6) 0.405(14) 0.198(7) -0.219(9) 0.078(5) -0.119(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag01 N1 2.156(4) 7_655 ? Ag01 N1 2.156(4) . ? Ag01 O2 2.450(6) . ? P1 F2 1.455(6) . ? P1 F2 1.455(6) 4_556 ? P1 F1 1.461(5) . ? P1 F1 1.461(5) 4_556 ? P1 F3 1.585(4) 4_556 ? P1 F3 1.585(4) . ? O1 C1 1.417(4) . ? O1 C4 1.455(4) . ? C4 C6 1.501(5) . ? C4 C3 1.533(4) . ? C4 H4 0.9800 . ? O2 H1O 0.77(5) . ? C3 C3 1.540(6) 7 ? C3 C2 1.562(5) . ? C3 H3 0.9800 . ? C6 C7 1.384(5) . ? C6 C6 1.397(7) 7 ? C1 C10 1.486(5) . ? C1 C2 1.514(5) . ? C1 H1 0.9800 . ? C7 C8 1.385(6) . ? C7 H7 0.9300 . ? C9 C2 1.529(5) 7 ? C9 C2 1.529(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N1 C10 1.133(5) . ? C2 H2 0.9800 . ? C8 C8 1.373(10) 7 ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag01 N1 151.3(2) 7_655 . ? N1 Ag01 O2 104.30(12) 7_655 . ? N1 Ag01 O2 104.30(12) . . ? F2 P1 F2 95.3(11) . 4_556 ? F2 P1 F1 88.2(7) . . ? F2 P1 F1 176.5(9) 4_556 . ? F2 P1 F1 176.5(8) . 4_556 ? F2 P1 F1 88.2(7) 4_556 4_556 ? F1 P1 F1 88.4(11) . 4_556 ? F2 P1 F3 91.0(3) . 4_556 ? F2 P1 F3 90.6(3) 4_556 4_556 ? F1 P1 F3 89.6(3) . 4_556 ? F1 P1 F3 88.8(3) 4_556 4_556 ? F2 P1 F3 90.6(3) . . ? F2 P1 F3 91.0(3) 4_556 . ? F1 P1 F3 88.8(3) . . ? F1 P1 F3 89.6(4) 4_556 . ? F3 P1 F3 177.7(4) 4_556 . ? C1 O1 C4 105.6(2) . . ? O1 C4 C6 107.5(2) . . ? O1 C4 C3 106.1(3) . . ? C6 C4 C3 118.2(3) . . ? O1 C4 H4 108.2 . . ? C6 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? Ag01 O2 H1O 109(4) . . ? C4 C3 C3 117.85(17) . 7 ? C4 C3 C2 103.5(2) . . ? C3 C3 C2 106.84(17) 7 . ? C4 C3 H3 109.4 . . ? C3 C3 H3 109.4 7 . ? C2 C3 H3 109.4 . . ? C7 C6 C6 119.3(2) . 7 ? C7 C6 C4 119.1(3) . . ? C6 C6 C4 121.67(18) 7 . ? O1 C1 C10 108.7(3) . . ? O1 C1 C2 105.2(3) . . ? C10 C1 C2 113.8(3) . . ? O1 C1 H1 109.7 . . ? C10 C1 H1 109.7 . . ? C2 C1 H1 109.7 . . ? C6 C7 C8 121.0(4) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C2 C9 C2 106.2(4) 7 . ? C2 C9 H9A 110.5 7 . ? C2 C9 H9A 110.5 . . ? C2 C9 H9B 110.5 7 . ? C2 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C10 N1 Ag01 169.5(4) . . ? N1 C10 C1 176.3(4) . . ? C1 C2 C9 110.7(3) . . ? C1 C2 C3 103.5(3) . . ? C9 C2 C3 104.9(3) . . ? C1 C2 H2 112.4 . . ? C9 C2 H2 112.4 . . ? C3 C2 H2 112.4 . . ? C8 C8 C7 119.8(3) 7 . ? C8 C8 H8 120.1 7 . ? C7 C8 H8 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C4 C6 -162.1(3) . . . . ? C1 O1 C4 C3 -34.7(3) . . . . ? O1 C4 C3 C3 -103.8(2) . . . 7 ? C6 C4 C3 C3 16.8(3) . . . 7 ? O1 C4 C3 C2 13.9(3) . . . . ? C6 C4 C3 C2 134.4(3) . . . . ? O1 C4 C6 C7 -76.4(4) . . . . ? C3 C4 C6 C7 163.7(3) . . . . ? O1 C4 C6 C6 102.4(2) . . . 7 ? C3 C4 C6 C6 -17.5(3) . . . 7 ? C4 O1 C1 C10 -80.5(3) . . . . ? C4 O1 C1 C2 41.8(3) . . . . ? C6 C6 C7 C8 -0.5(6) 7 . . . ? C4 C6 C7 C8 178.4(4) . . . . ? N1 Ag01 N1 C10 44(2) 7_655 . . . ? O2 Ag01 N1 C10 -140(2) . . . . ? Ag01 N1 C10 C1 -82(7) . . . . ? O1 C1 C10 N1 -35(7) . . . . ? C2 C1 C10 N1 -152(7) . . . . ? O1 C1 C2 C9 80.3(4) . . . . ? C10 C1 C2 C9 -160.8(3) . . . . ? O1 C1 C2 C3 -31.6(3) . . . . ? C10 C1 C2 C3 87.3(3) . . . . ? C2 C9 C2 C1 -142.4(3) 7 . . . ? C2 C9 C2 C3 -31.4(5) 7 . . . ? C4 C3 C2 C1 10.1(3) . . . . ? C3 C3 C2 C1 135.2(2) 7 . . . ? C4 C3 C2 C9 -106.0(3) . . . . ? C3 C3 C2 C9 19.1(3) 7 . . . ? C6 C7 C8 C8 0.5(6) . . . 7 ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.243 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 942150' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N2 O2' _chemical_formula_sum 'C11 H12 N2 O2' _chemical_formula_weight 204.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1344(2) _cell_length_b 9.0828(3) _cell_length_c 16.2936(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.446(2) _cell_angle_gamma 90.00 _cell_volume 1031.02(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3417 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.08 _exptl_crystal_description Block _exptl_crystal_colour white _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details 'Sadabs (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'Phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6013 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1694 _reflns_number_gt 1423 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1694 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _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 0.7740(2) 0.75645(16) -0.06721(9) 0.0402(4) Uani 1 1 d . . . H1 H 0.8756 0.8050 -0.0892 0.048 Uiso 1 1 calc R . . C2 C 0.8595(2) 0.68464(14) 0.01771(9) 0.0349(4) Uani 1 1 d . . . H2 H 0.8763 0.5785 0.0112 0.042 Uiso 1 1 calc R . . C3 C 1.0455(2) 0.75540(17) 0.06582(10) 0.0410(4) Uani 1 1 d . . . H3A H 1.0604 0.8537 0.0448 0.049 Uiso 1 1 calc R . . H3B H 1.1558 0.6966 0.0606 0.049 Uiso 1 1 calc R . . C4 C 1.0246(2) 0.76094(15) 0.15710(9) 0.0363(4) Uani 1 1 d . . . H4 H 1.0598 0.6674 0.1863 0.044 Uiso 1 1 calc R . . C5 C 1.1256(2) 0.89126(15) 0.20622(9) 0.0404(4) Uani 1 1 d . . . H5 H 1.2534 0.9046 0.1943 0.048 Uiso 1 1 calc R . . C6 C 0.8142(2) 0.96678(15) 0.14484(10) 0.0432(4) Uani 1 1 d . . . H6A H 0.7720 0.9992 0.0871 0.052 Uiso 1 1 calc R . . H6B H 0.7282 1.0077 0.1776 0.052 Uiso 1 1 calc R . . C7 C 0.8126(2) 0.79791(14) 0.14928(9) 0.0348(4) Uani 1 1 d . . . H7 H 0.7685 0.7648 0.1992 0.042 Uiso 1 1 calc R . . C8 C 0.70613(19) 0.71580(15) 0.07086(9) 0.0342(4) Uani 1 1 d . . . H8 H 0.6560 0.6225 0.0874 0.041 Uiso 1 1 calc R . . C9 C 0.5488(2) 0.79705(17) 0.01013(10) 0.0446(4) Uani 1 1 d . . . H9A H 0.4491 0.7293 -0.0166 0.053 Uiso 1 1 calc R . . H9B H 0.4916 0.8721 0.0393 0.053 Uiso 1 1 calc R . . C10 C 0.6749(2) 0.64544(19) -0.12884(10) 0.0481(5) Uani 1 1 d . . . C11 C 1.1402(2) 0.87218(15) 0.29776(11) 0.0400(4) Uani 1 1 d . . . N1 N 0.6008(2) 0.5588(2) -0.17497(11) 0.0722(5) Uani 1 1 d . . . N2 N 1.1440(2) 0.85968(15) 0.36782(9) 0.0529(4) Uani 1 1 d . . . O1 O 0.64069(16) 0.86287(11) -0.05119(7) 0.0486(4) Uani 1 1 d . . . O2 O 1.00820(15) 1.01537(11) 0.17821(7) 0.0492(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0437(9) 0.0404(8) 0.0379(10) 0.0017(6) 0.0116(7) 0.0053(6) C2 0.0402(8) 0.0298(7) 0.0355(9) -0.0001(6) 0.0101(7) 0.0058(6) C3 0.0360(8) 0.0469(8) 0.0416(10) -0.0027(6) 0.0119(7) 0.0056(6) C4 0.0386(8) 0.0320(7) 0.0368(10) 0.0028(6) 0.0047(7) 0.0033(5) C5 0.0403(8) 0.0395(8) 0.0402(10) 0.0020(6) 0.0062(7) -0.0008(6) C6 0.0462(9) 0.0345(8) 0.0476(10) -0.0030(6) 0.0070(7) 0.0062(6) C7 0.0404(8) 0.0340(8) 0.0321(8) 0.0022(5) 0.0125(6) 0.0008(5) C8 0.0368(8) 0.0319(7) 0.0350(9) 0.0002(5) 0.0100(7) -0.0003(5) C9 0.0387(9) 0.0496(9) 0.0457(10) -0.0045(6) 0.0096(7) 0.0087(6) C10 0.0446(9) 0.0648(11) 0.0358(10) -0.0016(8) 0.0105(8) 0.0065(7) C11 0.0395(9) 0.0352(8) 0.0422(11) -0.0022(6) 0.0021(8) -0.0032(5) N1 0.0642(11) 0.0954(14) 0.0564(11) -0.0272(9) 0.0118(8) -0.0077(9) N2 0.0589(10) 0.0521(9) 0.0445(10) -0.0014(6) 0.0040(8) -0.0067(6) O1 0.0565(7) 0.0446(6) 0.0446(7) 0.0085(4) 0.0104(6) 0.0171(5) O2 0.0583(7) 0.0306(6) 0.0537(8) 0.0067(4) 0.0011(6) -0.0051(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4190(18) . ? C1 C10 1.489(2) . ? C1 C2 1.532(2) . ? C1 H1 0.9800 . ? C2 C3 1.530(2) . ? C2 C8 1.561(2) . ? C2 H2 0.9800 . ? C3 C4 1.527(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.5207(19) . ? C4 C7 1.528(2) . ? C4 H4 0.9800 . ? C5 O2 1.4198(17) . ? C5 C11 1.483(2) . ? C5 H5 0.9800 . ? C6 O2 1.4426(19) . ? C6 C7 1.5356(19) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.5322(19) . ? C7 H7 0.9800 . ? C8 C9 1.518(2) . ? C8 H8 0.9800 . ? C9 O1 1.4382(19) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N1 1.137(2) . ? C11 N2 1.142(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C10 110.23(13) . . ? O1 C1 C2 106.02(12) . . ? C10 C1 C2 111.06(12) . . ? O1 C1 H1 109.8 . . ? C10 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? C3 C2 C1 114.61(12) . . ? C3 C2 C8 105.90(11) . . ? C1 C2 C8 103.51(11) . . ? C3 C2 H2 110.8 . . ? C1 C2 H2 110.8 . . ? C8 C2 H2 110.8 . . ? C2 C3 C4 104.88(12) . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3B 110.8 . . ? C4 C3 H3B 110.8 . . ? H3A C3 H3B 108.8 . . ? C5 C4 C3 113.80(12) . . ? C5 C4 C7 102.77(11) . . ? C3 C4 C7 103.22(11) . . ? C5 C4 H4 112.1 . . ? C3 C4 H4 112.1 . . ? C7 C4 H4 112.1 . . ? O2 C5 C11 108.96(12) . . ? O2 C5 C4 105.61(11) . . ? C11 C5 C4 111.17(12) . . ? O2 C5 H5 110.3 . . ? C11 C5 H5 110.3 . . ? C4 C5 H5 110.3 . . ? O2 C6 C7 107.70(11) . . ? O2 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? O2 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C4 C7 C8 105.46(11) . . ? C4 C7 C6 101.90(11) . . ? C8 C7 C6 117.02(11) . . ? C4 C7 H7 110.6 . . ? C8 C7 H7 110.6 . . ? C6 C7 H7 110.6 . . ? C9 C8 C7 118.10(11) . . ? C9 C8 C2 103.58(11) . . ? C7 C8 C2 105.67(11) . . ? C9 C8 H8 109.7 . . ? C7 C8 H8 109.7 . . ? C2 C8 H8 109.7 . . ? O1 C9 C8 105.72(12) . . ? O1 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? O1 C9 H9B 110.6 . . ? C8 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? N1 C10 C1 178.79(19) . . ? N2 C11 C5 177.17(16) . . ? C1 O1 C9 105.58(11) . . ? C5 O2 C6 109.26(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -93.04(14) . . . . ? C10 C1 C2 C3 147.22(13) . . . . ? O1 C1 C2 C8 21.79(14) . . . . ? C10 C1 C2 C8 -97.95(13) . . . . ? C1 C2 C3 C4 138.19(12) . . . . ? C8 C2 C3 C4 24.76(14) . . . . ? C2 C3 C4 C5 -148.43(12) . . . . ? C2 C3 C4 C7 -37.83(13) . . . . ? C3 C4 C5 O2 75.48(14) . . . . ? C7 C4 C5 O2 -35.39(14) . . . . ? C3 C4 C5 C11 -166.48(12) . . . . ? C7 C4 C5 C11 82.64(13) . . . . ? C5 C4 C7 C8 155.08(11) . . . . ? C3 C4 C7 C8 36.50(13) . . . . ? C5 C4 C7 C6 32.40(14) . . . . ? C3 C4 C7 C6 -86.18(12) . . . . ? O2 C6 C7 C4 -19.44(15) . . . . ? O2 C6 C7 C8 -133.86(13) . . . . ? C4 C7 C8 C9 -136.37(12) . . . . ? C6 C7 C8 C9 -23.96(18) . . . . ? C4 C7 C8 C2 -21.14(13) . . . . ? C6 C7 C8 C2 91.27(13) . . . . ? C3 C2 C8 C9 122.58(12) . . . . ? C1 C2 C8 C9 1.67(13) . . . . ? C3 C2 C8 C7 -2.24(14) . . . . ? C1 C2 C8 C7 -123.16(11) . . . . ? C7 C8 C9 O1 92.09(14) . . . . ? C2 C8 C9 O1 -24.27(14) . . . . ? O1 C1 C10 N1 -131(9) . . . . ? C2 C1 C10 N1 -14(9) . . . . ? O2 C5 C11 N2 33(3) . . . . ? C4 C5 C11 N2 -83(3) . . . . ? C10 C1 O1 C9 81.92(15) . . . . ? C2 C1 O1 C9 -38.36(15) . . . . ? C8 C9 O1 C1 39.58(15) . . . . ? C11 C5 O2 C6 -95.78(14) . . . . ? C4 C5 O2 C6 23.71(15) . . . . ? C7 C6 O2 C5 -2.40(16) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.218 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.032 _vrf_PLAT029_new ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.928 RESPONSE: Even though crystal data was collected up to 0.73 \%A resolution, the crystal (the largest available) still diffracted quite weakly at high angle. On repeated recrystallisation we could get only small sized crystals. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 942151' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O2 ' _chemical_formula_sum ' C13 H14 N2 O2 ' _chemical_formula_weight 230.26 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8137(7) _cell_length_b 11.8850(4) _cell_length_c 12.8820(4) _cell_angle_alpha 115.1300(10) _cell_angle_beta 102.974(2) _cell_angle_gamma 95.330(2) _cell_volume 1163.07(11) _cell_formula_units_Z 4 _cell_measurement_temperature 275(2) _cell_measurement_reflns_used 6203 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 31.88 _exptl_crystal_description Block _exptl_crystal_colour white _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ' SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 275(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15330 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 32.71 _reflns_number_total 6562 _reflns_number_gt 4401 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0663P)^2^+0.2372P] 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 6562 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.7451(2) 0.67540(18) 0.24123(18) 0.0607(4) Uani 1 1 d . . . H1A H 0.8224 0.7569 0.2855 0.073 Uiso 1 1 calc R . . C2A C 0.5827(2) 0.69672(17) 0.18977(16) 0.0563(4) Uani 1 1 d . . . H2A H 0.5661 0.6812 0.1066 0.068 Uiso 1 1 calc R . . C3A C 0.5547(2) 0.82640(17) 0.2670(2) 0.0646(5) Uani 1 1 d . . . H3A1 H 0.5836 0.8870 0.2391 0.078 Uiso 1 1 calc R . . H3A2 H 0.6165 0.8584 0.3501 0.078 Uiso 1 1 calc R . . C4A C 0.37681(19) 0.80345(15) 0.25334(15) 0.0497(4) Uani 1 1 d . . . H4A H 0.3145 0.8028 0.1797 0.060 Uiso 1 1 calc R . . C5A C 0.33441(19) 0.89373(16) 0.36191(16) 0.0530(4) Uani 1 1 d . . . H5A H 0.4042 0.9778 0.3965 0.064 Uiso 1 1 calc R . . C6A C 0.3471(2) 0.70700(16) 0.38142(16) 0.0550(4) Uani 1 1 d . . . H6A H 0.2461 0.6659 0.3825 0.066 Uiso 1 1 calc R . . C7A C 0.4853(3) 0.6715(2) 0.44933(16) 0.0682(5) Uani 1 1 d . . . H7A1 H 0.5820 0.7351 0.4769 0.082 Uiso 1 1 calc R . . H7A2 H 0.4621 0.6705 0.5191 0.082 Uiso 1 1 calc R . . C8A C 0.5108(2) 0.54291(19) 0.37038(19) 0.0657(5) Uani 1 1 d . . . H8A1 H 0.5895 0.5178 0.4175 0.079 Uiso 1 1 calc R . . H8A2 H 0.4119 0.4802 0.3373 0.079 Uiso 1 1 calc R . . C9A C 0.56649(18) 0.54774(16) 0.27155(16) 0.0520(4) Uani 1 1 d . . . H9A H 0.5727 0.4616 0.2171 0.062 Uiso 1 1 calc R . . C10A C 0.46310(18) 0.60075(14) 0.19875(13) 0.0460(3) Uani 1 1 d . . . H10A H 0.4087 0.5317 0.1182 0.055 Uiso 1 1 calc R . . C11A C 0.34001(17) 0.67355(14) 0.25086(14) 0.0442(3) Uani 1 1 d . . . H11A H 0.2322 0.6279 0.1981 0.053 Uiso 1 1 calc R . . C12A C 0.8037(2) 0.5846(2) 0.1454(2) 0.0672(5) Uani 1 1 d . . . C13A C 0.1659(2) 0.90523(19) 0.3316(2) 0.0732(6) Uani 1 1 d . . . C1B C 1.05695(19) 0.29331(17) 0.09287(16) 0.0540(4) Uani 1 1 d . . . H1B H 1.0100 0.3419 0.0535 0.065 Uiso 1 1 calc R . . C2B C 0.92861(17) 0.18561(16) 0.07471(14) 0.0491(4) Uani 1 1 d . . . H2B H 0.9141 0.1089 -0.0006 0.059 Uiso 1 1 calc R . . C3B C 0.77128(17) 0.22493(19) 0.08687(15) 0.0553(4) Uani 1 1 d . . . H3B1 H 0.7892 0.3139 0.1441 0.066 Uiso 1 1 calc R . . H3B2 H 0.7032 0.2112 0.0102 0.066 Uiso 1 1 calc R . . C4B C 0.69713(16) 0.13963(15) 0.13132(13) 0.0444(3) Uani 1 1 d . . . H4B H 0.6330 0.0588 0.0647 0.053 Uiso 1 1 calc R . . C5B C 0.60275(16) 0.20624(14) 0.21677(14) 0.0452(3) Uani 1 1 d . . . H5B H 0.5584 0.2685 0.1949 0.054 Uiso 1 1 calc R . . C6B C 0.82685(18) 0.19269(16) 0.33900(14) 0.0512(4) Uani 1 1 d . . . H6B H 0.7860 0.1326 0.3649 0.061 Uiso 1 1 calc R . . C7B C 0.9807(2) 0.2788(2) 0.43074(15) 0.0680(5) Uani 1 1 d . . . H7B1 H 1.0559 0.2279 0.4434 0.082 Uiso 1 1 calc R . . H7B2 H 0.9608 0.3289 0.5065 0.082 Uiso 1 1 calc R . . C8B C 1.0507(2) 0.36628(19) 0.38782(15) 0.0620(5) Uani 1 1 d . . . H8B1 H 0.9718 0.4117 0.3688 0.074 Uiso 1 1 calc R . . H8B2 H 1.1416 0.4284 0.4514 0.074 Uiso 1 1 calc R . . C9B C 1.10236(17) 0.29277(16) 0.27830(14) 0.0511(4) Uani 1 1 d . . . H9B H 1.2084 0.2776 0.3043 0.061 Uiso 1 1 calc R . . C10B C 0.98980(16) 0.16361(14) 0.18431(13) 0.0436(3) Uani 1 1 d . . . H10B H 1.0511 0.0966 0.1648 0.052 Uiso 1 1 calc R . . C11B C 0.83975(16) 0.11924(14) 0.21174(13) 0.0421(3) Uani 1 1 d . . . H11B H 0.8271 0.0285 0.1901 0.051 Uiso 1 1 calc R . . C12B C 1.19037(19) 0.24571(17) 0.04690(15) 0.0535(4) Uani 1 1 d . . . C13B C 0.47017(17) 0.11725(15) 0.21433(15) 0.0466(3) Uani 1 1 d . . . N1A N 0.8468(3) 0.5150(2) 0.0714(2) 0.0954(6) Uani 1 1 d . . . N2A N 0.0377(2) 0.9152(2) 0.3085(3) 0.1198(9) Uani 1 1 d . . . N1B N 1.29551(19) 0.21163(17) 0.01427(16) 0.0698(4) Uani 1 1 d . . . N2B N 0.36580(17) 0.05118(15) 0.21096(16) 0.0633(4) Uani 1 1 d . . . O1A O 0.72282(13) 0.62793(13) 0.32078(11) 0.0635(3) Uani 1 1 d . . . O2A O 0.36522(18) 0.84414(12) 0.44458(11) 0.0680(4) Uani 1 1 d . . . O1B O 1.11316(15) 0.37093(11) 0.21802(11) 0.0633(3) Uani 1 1 d . . . O2B O 0.71345(12) 0.27146(11) 0.33138(10) 0.0550(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0539(9) 0.0647(11) 0.0752(12) 0.0356(10) 0.0322(9) 0.0147(8) C2A 0.0662(10) 0.0685(11) 0.0618(10) 0.0426(9) 0.0376(8) 0.0295(9) C3A 0.0682(10) 0.0548(10) 0.1031(15) 0.0511(11) 0.0505(11) 0.0214(9) C4A 0.0564(8) 0.0521(9) 0.0548(9) 0.0332(8) 0.0216(7) 0.0197(7) C5A 0.0538(8) 0.0465(9) 0.0650(10) 0.0277(8) 0.0232(8) 0.0152(7) C6A 0.0656(10) 0.0522(10) 0.0631(10) 0.0324(9) 0.0348(8) 0.0147(8) C7A 0.0980(14) 0.0754(13) 0.0512(10) 0.0424(10) 0.0280(10) 0.0267(11) C8A 0.0640(10) 0.0756(12) 0.0862(13) 0.0589(12) 0.0278(10) 0.0214(9) C9A 0.0506(8) 0.0465(9) 0.0620(10) 0.0294(8) 0.0129(7) 0.0108(7) C10A 0.0500(8) 0.0423(8) 0.0382(7) 0.0140(7) 0.0079(6) 0.0111(6) C11A 0.0397(7) 0.0442(8) 0.0469(8) 0.0211(7) 0.0094(6) 0.0072(6) C12A 0.0652(11) 0.0856(14) 0.0833(13) 0.0542(12) 0.0421(10) 0.0355(10) C13A 0.0614(11) 0.0595(11) 0.1159(18) 0.0467(12) 0.0405(11) 0.0221(9) C1B 0.0466(8) 0.0613(10) 0.0586(10) 0.0277(9) 0.0227(7) 0.0128(7) C2B 0.0413(7) 0.0560(10) 0.0412(8) 0.0143(7) 0.0140(6) 0.0065(7) C3B 0.0390(7) 0.0830(12) 0.0542(9) 0.0414(9) 0.0122(7) 0.0136(8) C4B 0.0342(6) 0.0478(9) 0.0413(7) 0.0145(7) 0.0073(5) 0.0034(6) C5B 0.0368(6) 0.0422(8) 0.0587(9) 0.0245(7) 0.0150(6) 0.0084(6) C6B 0.0483(8) 0.0578(10) 0.0458(8) 0.0235(8) 0.0126(6) 0.0076(7) C7B 0.0543(9) 0.0922(15) 0.0394(8) 0.0192(9) 0.0074(7) 0.0041(9) C8B 0.0450(8) 0.0658(11) 0.0422(8) 0.0012(8) 0.0075(7) -0.0057(8) C9B 0.0352(6) 0.0546(9) 0.0479(8) 0.0121(8) 0.0082(6) 0.0059(6) C10B 0.0374(6) 0.0408(8) 0.0450(8) 0.0119(7) 0.0124(6) 0.0122(6) C11B 0.0400(7) 0.0355(7) 0.0461(8) 0.0151(6) 0.0111(6) 0.0085(6) C12B 0.0464(8) 0.0635(11) 0.0552(9) 0.0298(9) 0.0189(7) 0.0094(7) C13B 0.0398(7) 0.0461(8) 0.0583(9) 0.0266(8) 0.0152(6) 0.0131(6) N1A 0.1021(14) 0.1275(17) 0.1012(15) 0.0676(14) 0.0622(13) 0.0702(14) N2A 0.0655(11) 0.1079(17) 0.219(3) 0.095(2) 0.0540(15) 0.0345(12) N1B 0.0587(9) 0.0890(12) 0.0775(11) 0.0442(10) 0.0343(8) 0.0226(8) N2B 0.0502(7) 0.0627(9) 0.0907(12) 0.0462(9) 0.0240(8) 0.0099(7) O1A 0.0447(6) 0.0911(9) 0.0614(7) 0.0428(7) 0.0131(5) 0.0120(6) O2A 0.1014(10) 0.0572(7) 0.0567(7) 0.0269(6) 0.0367(7) 0.0308(7) O1B 0.0668(7) 0.0497(7) 0.0621(8) 0.0151(6) 0.0255(6) -0.0014(6) O2B 0.0447(5) 0.0499(6) 0.0535(6) 0.0069(5) 0.0184(5) 0.0077(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A O1A 1.403(2) . ? C1A C12A 1.487(3) . ? C1A C2A 1.529(2) . ? C1A H1A 0.9800 . ? C2A C3A 1.518(2) . ? C2A C10A 1.539(2) . ? C2A H2A 0.9800 . ? C3A C4A 1.523(2) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.511(2) . ? C4A C11A 1.533(2) . ? C4A H4A 0.9800 . ? C5A O2A 1.410(2) . ? C5A C13A 1.483(3) . ? C5A H5A 0.9800 . ? C6A O2A 1.453(2) . ? C6A C7A 1.536(3) . ? C6A C11A 1.540(2) . ? C6A H6A 0.9800 . ? C7A C8A 1.506(3) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C9A 1.484(2) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A O1A 1.435(2) . ? C9A C10A 1.527(2) . ? C9A H9A 0.9800 . ? C10A C11A 1.544(2) . ? C10A H10A 0.9800 . ? C11A H11A 0.9800 . ? C12A N1A 1.135(3) . ? C13A N2A 1.133(3) . ? C1B O1B 1.410(2) . ? C1B C12B 1.485(2) . ? C1B C2B 1.527(2) . ? C1B H1B 0.9800 . ? C2B C3B 1.524(2) . ? C2B C10B 1.533(2) . ? C2B H2B 0.9800 . ? C3B C4B 1.523(2) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.524(2) . ? C4B C11B 1.5483(19) . ? C4B H4B 0.9800 . ? C5B O2B 1.4047(19) . ? C5B C13B 1.487(2) . ? C5B H5B 0.9800 . ? C6B O2B 1.447(2) . ? C6B C7B 1.510(2) . ? C6B C11B 1.533(2) . ? C6B H6B 0.9800 . ? C7B C8B 1.513(3) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B C9B 1.509(2) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B O1B 1.451(2) . ? C9B C10B 1.551(2) . ? C9B H9B 0.9800 . ? C10B C11B 1.546(2) . ? C10B H10B 0.9800 . ? C11B H11B 0.9800 . ? C12B N1B 1.140(2) . ? C13B N2B 1.133(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1A C1A C12A 111.02(15) . . ? O1A C1A C2A 105.70(12) . . ? C12A C1A C2A 111.70(17) . . ? O1A C1A H1A 109.4 . . ? C12A C1A H1A 109.4 . . ? C2A C1A H1A 109.4 . . ? C3A C2A C1A 112.95(17) . . ? C3A C2A C10A 105.12(12) . . ? C1A C2A C10A 103.86(13) . . ? C3A C2A H2A 111.5 . . ? C1A C2A H2A 111.5 . . ? C10A C2A H2A 111.5 . . ? C2A C3A C4A 104.55(15) . . ? C2A C3A H3A1 110.8 . . ? C4A C3A H3A1 110.8 . . ? C2A C3A H3A2 110.8 . . ? C4A C3A H3A2 110.8 . . ? H3A1 C3A H3A2 108.9 . . ? C5A C4A C3A 113.40(15) . . ? C5A C4A C11A 104.26(12) . . ? C3A C4A C11A 103.85(12) . . ? C5A C4A H4A 111.6 . . ? C3A C4A H4A 111.6 . . ? C11A C4A H4A 111.6 . . ? O2A C5A C13A 111.45(15) . . ? O2A C5A C4A 105.72(12) . . ? C13A C5A C4A 112.00(16) . . ? O2A C5A H5A 109.2 . . ? C13A C5A H5A 109.2 . . ? C4A C5A H5A 109.2 . . ? O2A C6A C7A 107.56(15) . . ? O2A C6A C11A 106.56(12) . . ? C7A C6A C11A 115.51(14) . . ? O2A C6A H6A 109.0 . . ? C7A C6A H6A 109.0 . . ? C11A C6A H6A 109.0 . . ? C8A C7A C6A 111.06(16) . . ? C8A C7A H7A1 109.4 . . ? C6A C7A H7A1 109.4 . . ? C8A C7A H7A2 109.4 . . ? C6A C7A H7A2 109.4 . . ? H7A1 C7A H7A2 108.0 . . ? C9A C8A C7A 109.92(14) . . ? C9A C8A H8A1 109.7 . . ? C7A C8A H8A1 109.7 . . ? C9A C8A H8A2 109.7 . . ? C7A C8A H8A2 109.7 . . ? H8A1 C8A H8A2 108.2 . . ? O1A C9A C8A 109.08(15) . . ? O1A C9A C10A 106.44(12) . . ? C8A C9A C10A 115.22(14) . . ? O1A C9A H9A 108.6 . . ? C8A C9A H9A 108.6 . . ? C10A C9A H9A 108.6 . . ? C9A C10A C2A 104.40(12) . . ? C9A C10A C11A 118.22(13) . . ? C2A C10A C11A 106.48(12) . . ? C9A C10A H10A 109.1 . . ? C2A C10A H10A 109.1 . . ? C11A C10A H10A 109.1 . . ? C4A C11A C6A 103.83(13) . . ? C4A C11A C10A 105.73(12) . . ? C6A C11A C10A 117.82(12) . . ? C4A C11A H11A 109.7 . . ? C6A C11A H11A 109.7 . . ? C10A C11A H11A 109.7 . . ? N1A C12A C1A 179.3(2) . . ? N2A C13A C5A 179.3(2) . . ? O1B C1B C12B 109.80(14) . . ? O1B C1B C2B 105.05(13) . . ? C12B C1B C2B 112.13(14) . . ? O1B C1B H1B 109.9 . . ? C12B C1B H1B 109.9 . . ? C2B C1B H1B 109.9 . . ? C3B C2B C1B 113.21(14) . . ? C3B C2B C10B 103.57(12) . . ? C1B C2B C10B 103.83(12) . . ? C3B C2B H2B 111.9 . . ? C1B C2B H2B 111.9 . . ? C10B C2B H2B 111.9 . . ? C4B C3B C2B 104.35(13) . . ? C4B C3B H3B1 110.9 . . ? C2B C3B H3B1 110.9 . . ? C4B C3B H3B2 110.9 . . ? C2B C3B H3B2 110.9 . . ? H3B1 C3B H3B2 108.9 . . ? C3B C4B C5B 112.56(13) . . ? C3B C4B C11B 105.15(11) . . ? C5B C4B C11B 103.74(12) . . ? C3B C4B H4B 111.6 . . ? C5B C4B H4B 111.6 . . ? C11B C4B H4B 111.6 . . ? O2B C5B C13B 111.29(13) . . ? O2B C5B C4B 106.03(11) . . ? C13B C5B C4B 113.19(13) . . ? O2B C5B H5B 108.7 . . ? C13B C5B H5B 108.7 . . ? C4B C5B H5B 108.7 . . ? O2B C6B C7B 107.84(14) . . ? O2B C6B C11B 106.00(12) . . ? C7B C6B C11B 114.45(13) . . ? O2B C6B H6B 109.5 . . ? C7B C6B H6B 109.5 . . ? C11B C6B H6B 109.5 . . ? C6B C7B C8B 109.96(14) . . ? C6B C7B H7B1 109.7 . . ? C8B C7B H7B1 109.7 . . ? C6B C7B H7B2 109.7 . . ? C8B C7B H7B2 109.7 . . ? H7B1 C7B H7B2 108.2 . . ? C9B C8B C7B 111.26(16) . . ? C9B C8B H8B1 109.4 . . ? C7B C8B H8B1 109.4 . . ? C9B C8B H8B2 109.4 . . ? C7B C8B H8B2 109.4 . . ? H8B1 C8B H8B2 108.0 . . ? O1B C9B C8B 107.93(14) . . ? O1B C9B C10B 106.97(12) . . ? C8B C9B C10B 115.90(13) . . ? O1B C9B H9B 108.6 . . ? C8B C9B H9B 108.6 . . ? C10B C9B H9B 108.6 . . ? C2B C10B C11B 105.91(11) . . ? C2B C10B C9B 103.20(13) . . ? C11B C10B C9B 118.25(12) . . ? C2B C10B H10B 109.7 . . ? C11B C10B H10B 109.7 . . ? C9B C10B H10B 109.7 . . ? C6B C11B C10B 117.74(12) . . ? C6B C11B C4B 104.34(11) . . ? C10B C11B C4B 106.02(12) . . ? C6B C11B H11B 109.5 . . ? C10B C11B H11B 109.5 . . ? C4B C11B H11B 109.5 . . ? N1B C12B C1B 178.2(2) . . ? N2B C13B C5B 177.81(16) . . ? C1A O1A C9A 107.96(13) . . ? C5A O2A C6A 110.11(13) . . ? C1B O1B C9B 109.37(12) . . ? C5B O2B C6B 107.44(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A C2A C3A 86.75(17) . . . . ? C12A C1A C2A C3A -152.39(15) . . . . ? O1A C1A C2A C10A -26.59(18) . . . . ? C12A C1A C2A C10A 94.27(16) . . . . ? C1A C2A C3A C4A -145.84(14) . . . . ? C10A C2A C3A C4A -33.27(18) . . . . ? C2A C3A C4A C5A 150.85(14) . . . . ? C2A C3A C4A C11A 38.32(17) . . . . ? C3A C4A C5A O2A -80.97(16) . . . . ? C11A C4A C5A O2A 31.31(16) . . . . ? C3A C4A C5A C13A 157.47(15) . . . . ? C11A C4A C5A C13A -90.25(16) . . . . ? O2A C6A C7A C8A -160.00(15) . . . . ? C11A C6A C7A C8A -41.2(2) . . . . ? C6A C7A C8A C9A 66.3(2) . . . . ? C7A C8A C9A O1A 67.00(18) . . . . ? C7A C8A C9A C10A -52.6(2) . . . . ? O1A C9A C10A C2A 11.91(17) . . . . ? C8A C9A C10A C2A 132.95(16) . . . . ? O1A C9A C10A C11A -106.14(16) . . . . ? C8A C9A C10A C11A 14.9(2) . . . . ? C3A C2A C10A C9A -110.43(15) . . . . ? C1A C2A C10A C9A 8.43(17) . . . . ? C3A C2A C10A C11A 15.38(17) . . . . ? C1A C2A C10A C11A 134.24(13) . . . . ? C5A C4A C11A C6A -22.70(15) . . . . ? C3A C4A C11A C6A 96.29(15) . . . . ? C5A C4A C11A C10A -147.36(12) . . . . ? C3A C4A C11A C10A -28.37(17) . . . . ? O2A C6A C11A C4A 6.91(16) . . . . ? C7A C6A C11A C4A -112.47(16) . . . . ? O2A C6A C11A C10A 123.37(15) . . . . ? C7A C6A C11A C10A 4.0(2) . . . . ? C9A C10A C11A C4A 125.04(14) . . . . ? C2A C10A C11A C4A 8.10(16) . . . . ? C9A C10A C11A C6A 9.6(2) . . . . ? C2A C10A C11A C6A -107.33(15) . . . . ? O1A C1A C12A N1A 111(18) . . . . ? C2A C1A C12A N1A -7(18) . . . . ? O2A C5A C13A N2A 142(27) . . . . ? C4A C5A C13A N2A -100(27) . . . . ? O1B C1B C2B C3B 77.37(16) . . . . ? C12B C1B C2B C3B -163.43(14) . . . . ? O1B C1B C2B C10B -34.25(15) . . . . ? C12B C1B C2B C10B 84.96(16) . . . . ? C1B C2B C3B C4B -151.12(14) . . . . ? C10B C2B C3B C4B -39.34(16) . . . . ? C2B C3B C4B C5B 145.57(13) . . . . ? C2B C3B C4B C11B 33.31(16) . . . . ? C3B C4B C5B O2B -86.15(14) . . . . ? C11B C4B C5B O2B 26.98(15) . . . . ? C3B C4B C5B C13B 151.56(13) . . . . ? C11B C4B C5B C13B -95.30(14) . . . . ? O2B C6B C7B C8B -64.71(18) . . . . ? C11B C6B C7B C8B 53.0(2) . . . . ? C6B C7B C8B C9B -66.42(19) . . . . ? C7B C8B C9B O1B 159.85(13) . . . . ? C7B C8B C9B C10B 40.0(2) . . . . ? C3B C2B C10B C11B 30.10(15) . . . . ? C1B C2B C10B C11B 148.58(12) . . . . ? C3B C2B C10B C9B -94.81(14) . . . . ? C1B C2B C10B C9B 23.67(14) . . . . ? O1B C9B C10B C2B -5.95(14) . . . . ? C8B C9B C10B C2B 114.45(16) . . . . ? O1B C9B C10B C11B -122.41(13) . . . . ? C8B C9B C10B C11B -2.0(2) . . . . ? O2B C6B C11B C10B 104.00(14) . . . . ? C7B C6B C11B C10B -14.7(2) . . . . ? O2B C6B C11B C4B -13.14(15) . . . . ? C7B C6B C11B C4B -131.86(16) . . . . ? C2B C10B C11B C6B -125.97(14) . . . . ? C9B C10B C11B C6B -10.96(19) . . . . ? C2B C10B C11B C4B -9.73(15) . . . . ? C9B C10B C11B C4B 105.27(15) . . . . ? C3B C4B C11B C6B 110.59(14) . . . . ? C5B C4B C11B C6B -7.80(15) . . . . ? C3B C4B C11B C10B -14.39(15) . . . . ? C5B C4B C11B C10B -132.77(12) . . . . ? O1B C1B C12B N1B -18(6) . . . . ? C2B C1B C12B N1B -135(6) . . . . ? O2B C5B C13B N2B 127(5) . . . . ? C4B C5B C13B N2B -113(5) . . . . ? C12A C1A O1A C9A -85.59(17) . . . . ? C2A C1A O1A C9A 35.71(18) . . . . ? C8A C9A O1A C1A -154.99(14) . . . . ? C10A C9A O1A C1A -30.08(17) . . . . ? C13A C5A O2A C6A 93.89(17) . . . . ? C4A C5A O2A C6A -28.02(18) . . . . ? C7A C6A O2A C5A 137.50(14) . . . . ? C11A C6A O2A C5A 13.07(18) . . . . ? C12B C1B O1B C9B -89.18(15) . . . . ? C2B C1B O1B C9B 31.58(16) . . . . ? C8B C9B O1B C1B -141.43(13) . . . . ? C10B C9B O1B C1B -16.07(15) . . . . ? C13B C5B O2B C6B 86.58(14) . . . . ? C4B C5B O2B C6B -36.90(15) . . . . ? C7B C6B O2B C5B 154.44(13) . . . . ? C11B C6B O2B C5B 31.44(15) . . . . ? _diffrn_measured_fraction_theta_max 0.764 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.389 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 942152' ####################################################################### # # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 N2 O2' _chemical_formula_sum 'C17 H14 N2 O2' _chemical_formula_weight 278.30 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3570(6) _cell_length_b 9.7318(10) _cell_length_c 9.7501(5) _cell_angle_alpha 103.814(4) _cell_angle_beta 117.360(3) _cell_angle_gamma 104.070(4) _cell_volume 698.71(9) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4140 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details 'SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10370 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 32.50 _reflns_number_total 4400 _reflns_number_gt 3019 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0561P)^2^+0.0762P] 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 4400 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 1.27332(17) 0.97424(14) 0.77570(16) 0.0482(3) Uani 1 1 d . . . H1 H 1.3783 1.0206 0.7845 0.058 Uiso 1 1 calc R . . C2 C 1.27078(19) 1.00173(15) 0.91908(17) 0.0555(3) Uani 1 1 d . . . H2 H 1.3743 1.0642 1.0245 0.067 Uiso 1 1 calc R . . C3 C 1.1151(2) 0.93689(16) 0.90698(17) 0.0560(4) Uani 1 1 d . . . H3 H 1.1133 0.9552 1.0042 0.067 Uiso 1 1 calc R . . C4 C 0.96214(18) 0.84493(14) 0.75088(16) 0.0487(3) Uani 1 1 d . . . H4 H 0.8566 0.8037 0.7430 0.058 Uiso 1 1 calc R . . C5 C 0.96312(15) 0.81264(12) 0.60425(14) 0.0383(2) Uani 1 1 d . . . C6 C 0.79608(15) 0.69998(12) 0.43973(14) 0.0390(3) Uani 1 1 d . . . H6 H 0.6996 0.7284 0.4309 0.047 Uiso 1 1 calc R . . C7 C 0.65298(16) 0.43657(13) 0.28084(14) 0.0434(3) Uani 1 1 d . . . H7 H 0.6654 0.3388 0.2773 0.052 Uiso 1 1 calc R . . C8 C 0.72124(16) 0.50036(13) 0.18447(14) 0.0408(3) Uani 1 1 d . . . H8 H 0.6286 0.4614 0.0645 0.049 Uiso 1 1 calc R . . C9 C 0.88264(17) 0.47224(14) 0.20989(17) 0.0495(3) Uani 1 1 d . . . H9A H 0.8490 0.3772 0.1199 0.059 Uiso 1 1 calc R . . H9B H 0.9461 0.4647 0.3173 0.059 Uiso 1 1 calc R . . C10 C 0.99559(17) 0.61198(15) 0.20681(15) 0.0462(3) Uani 1 1 d . . . H10 H 0.9631 0.5972 0.0917 0.055 Uiso 1 1 calc R . . C11 C 1.19139(17) 0.65561(16) 0.32529(16) 0.0473(3) Uani 1 1 d . . . H11 H 1.2116 0.5613 0.3245 0.057 Uiso 1 1 calc R . . C12 C 1.13472(15) 0.83981(13) 0.46674(15) 0.0405(3) Uani 1 1 d . . . H12 H 1.2034 0.9364 0.4710 0.049 Uiso 1 1 calc R . . C13 C 1.12017(15) 0.87746(12) 0.61673(15) 0.0391(3) Uani 1 1 d . . . C14 C 0.79018(15) 0.67805(12) 0.27568(14) 0.0376(2) Uani 1 1 d . . . H14 H 0.7052 0.7141 0.2072 0.045 Uiso 1 1 calc R . . C15 C 0.96520(16) 0.74943(13) 0.28943(15) 0.0407(3) Uani 1 1 d . . . H15 H 0.9537 0.8151 0.2262 0.049 Uiso 1 1 calc R . . C16 C 0.46662(18) 0.41178(14) 0.21441(16) 0.0477(3) Uani 1 1 d . . . C17 C 1.3007(2) 0.7468(2) 0.2806(2) 0.0658(4) Uani 1 1 d . . . N1 N 1.3835(2) 0.8154(3) 0.2450(2) 0.1091(6) Uani 1 1 d . . . N2 N 0.32430(18) 0.39377(16) 0.16390(17) 0.0680(4) Uani 1 1 d . . . O1 O 1.23356(11) 0.74351(10) 0.48738(10) 0.0449(2) Uani 1 1 d . . . O2 O 0.76398(12) 0.54980(9) 0.44881(10) 0.0479(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0399(7) 0.0406(6) 0.0534(7) 0.0134(5) 0.0214(6) 0.0146(5) C2 0.0499(8) 0.0489(7) 0.0460(7) 0.0056(5) 0.0167(6) 0.0213(6) C3 0.0632(9) 0.0571(7) 0.0461(7) 0.0116(6) 0.0310(7) 0.0294(7) C4 0.0504(8) 0.0475(6) 0.0513(7) 0.0136(5) 0.0327(6) 0.0215(6) C5 0.0400(6) 0.0336(5) 0.0431(6) 0.0140(4) 0.0236(5) 0.0177(5) C6 0.0371(6) 0.0380(5) 0.0445(6) 0.0179(5) 0.0234(5) 0.0163(5) C7 0.0436(7) 0.0362(5) 0.0396(6) 0.0161(5) 0.0169(5) 0.0122(5) C8 0.0388(6) 0.0425(6) 0.0359(6) 0.0161(5) 0.0166(5) 0.0169(5) C9 0.0482(7) 0.0438(6) 0.0540(7) 0.0155(5) 0.0265(6) 0.0227(6) C10 0.0479(7) 0.0595(7) 0.0411(6) 0.0234(6) 0.0271(6) 0.0283(6) C11 0.0477(7) 0.0613(7) 0.0491(7) 0.0272(6) 0.0329(6) 0.0287(6) C12 0.0394(6) 0.0396(5) 0.0497(7) 0.0243(5) 0.0260(5) 0.0175(5) C13 0.0383(6) 0.0335(5) 0.0463(6) 0.0166(4) 0.0225(5) 0.0171(5) C14 0.0352(6) 0.0402(5) 0.0412(6) 0.0225(5) 0.0192(5) 0.0191(5) C15 0.0421(6) 0.0474(6) 0.0450(6) 0.0293(5) 0.0259(5) 0.0223(5) C16 0.0470(8) 0.0445(6) 0.0448(7) 0.0181(5) 0.0240(6) 0.0114(5) C17 0.0578(9) 0.0901(11) 0.0670(10) 0.0391(9) 0.0431(8) 0.0307(8) N1 0.0917(13) 0.1482(17) 0.1132(14) 0.0697(13) 0.0754(12) 0.0314(12) N2 0.0517(8) 0.0807(9) 0.0679(8) 0.0288(7) 0.0341(7) 0.0204(7) O1 0.0433(5) 0.0584(5) 0.0449(5) 0.0259(4) 0.0265(4) 0.0291(4) O2 0.0526(5) 0.0388(4) 0.0365(4) 0.0166(3) 0.0177(4) 0.0080(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3716(19) . ? C1 C13 1.3957(17) . ? C1 H1 0.9300 . ? C2 C3 1.376(2) . ? C2 H2 0.9300 . ? C3 C4 1.3748(19) . ? C3 H3 0.9300 . ? C4 C5 1.3934(17) . ? C4 H4 0.9300 . ? C5 C13 1.3858(16) . ? C5 C6 1.4969(16) . ? C6 O2 1.4516(13) . ? C6 C14 1.5353(16) . ? C6 H6 0.9800 . ? C7 O2 1.4119(14) . ? C7 C16 1.4836(19) . ? C7 C8 1.5211(17) . ? C7 H7 0.9800 . ? C8 C9 1.5187(17) . ? C8 C14 1.5470(16) . ? C8 H8 0.9800 . ? C9 C10 1.5221(18) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.5211(18) . ? C10 C15 1.5491(17) . ? C10 H10 0.9800 . ? C11 O1 1.4149(15) . ? C11 C17 1.4760(19) . ? C11 H11 0.9800 . ? C12 O1 1.4542(13) . ? C12 C13 1.4977(17) . ? C12 C15 1.5340(17) . ? C12 H12 0.9800 . ? C14 C15 1.5437(16) . ? C14 H14 0.9800 . ? C15 H15 0.9800 . ? C16 N2 1.1354(17) . ? C17 N1 1.128(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C13 120.78(13) . . ? C2 C1 H1 119.6 . . ? C13 C1 H1 119.6 . . ? C1 C2 C3 120.04(13) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.83(13) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.88(13) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C13 C5 C4 119.19(11) . . ? C13 C5 C6 122.29(10) . . ? C4 C5 C6 118.39(11) . . ? O2 C6 C5 106.03(9) . . ? O2 C6 C14 106.17(9) . . ? C5 C6 C14 118.60(10) . . ? O2 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? C14 C6 H6 108.6 . . ? O2 C7 C16 110.20(10) . . ? O2 C7 C8 104.75(9) . . ? C16 C7 C8 112.82(10) . . ? O2 C7 H7 109.6 . . ? C16 C7 H7 109.6 . . ? C8 C7 H7 109.6 . . ? C9 C8 C7 111.79(10) . . ? C9 C8 C14 104.93(9) . . ? C7 C8 C14 103.71(9) . . ? C9 C8 H8 112.0 . . ? C7 C8 H8 112.0 . . ? C14 C8 H8 112.0 . . ? C8 C9 C10 105.18(9) . . ? C8 C9 H9A 110.7 . . ? C10 C9 H9A 110.7 . . ? C8 C9 H9B 110.7 . . ? C10 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? C11 C10 C9 111.71(10) . . ? C11 C10 C15 103.92(10) . . ? C9 C10 C15 104.68(10) . . ? C11 C10 H10 112.0 . . ? C9 C10 H10 112.0 . . ? C15 C10 H10 112.0 . . ? O1 C11 C17 110.58(12) . . ? O1 C11 C10 104.91(9) . . ? C17 C11 C10 112.80(11) . . ? O1 C11 H11 109.5 . . ? C17 C11 H11 109.5 . . ? C10 C11 H11 109.5 . . ? O1 C12 C13 105.66(8) . . ? O1 C12 C15 106.06(9) . . ? C13 C12 C15 118.78(10) . . ? O1 C12 H12 108.6 . . ? C13 C12 H12 108.6 . . ? C15 C12 H12 108.6 . . ? C5 C13 C1 119.23(11) . . ? C5 C13 C12 122.40(10) . . ? C1 C13 C12 118.26(11) . . ? C6 C14 C15 118.22(9) . . ? C6 C14 C8 103.83(8) . . ? C15 C14 C8 106.23(9) . . ? C6 C14 H14 109.4 . . ? C15 C14 H14 109.4 . . ? C8 C14 H14 109.4 . . ? C12 C15 C14 117.91(9) . . ? C12 C15 C10 104.14(9) . . ? C14 C15 C10 106.48(9) . . ? C12 C15 H15 109.3 . . ? C14 C15 H15 109.3 . . ? C10 C15 H15 109.3 . . ? N2 C16 C7 179.57(13) . . ? N1 C17 C11 179.4(2) . . ? C11 O1 C12 107.44(8) . . ? C7 O2 C6 106.91(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 C1 C2 C3 -1.72(19) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 1.8(2) . . . . ? C3 C4 C5 C13 -1.51(18) . . . . ? C3 C4 C5 C6 174.34(11) . . . . ? C13 C5 C6 O2 107.87(11) . . . . ? C4 C5 C6 O2 -67.84(13) . . . . ? C13 C5 C6 C14 -11.24(15) . . . . ? C4 C5 C6 C14 173.05(10) . . . . ? O2 C7 C8 C9 80.22(12) . . . . ? C16 C7 C8 C9 -159.89(10) . . . . ? O2 C7 C8 C14 -32.31(12) . . . . ? C16 C7 C8 C14 87.57(11) . . . . ? C7 C8 C9 C10 -146.32(10) . . . . ? C14 C8 C9 C10 -34.54(12) . . . . ? C8 C9 C10 C11 146.10(10) . . . . ? C8 C9 C10 C15 34.26(12) . . . . ? C9 C10 C11 O1 -81.33(12) . . . . ? C15 C10 C11 O1 30.98(12) . . . . ? C9 C10 C11 C17 158.25(12) . . . . ? C15 C10 C11 C17 -89.44(13) . . . . ? C4 C5 C13 C1 -0.38(16) . . . . ? C6 C5 C13 C1 -176.06(10) . . . . ? C4 C5 C13 C12 175.68(10) . . . . ? C6 C5 C13 C12 0.01(16) . . . . ? C2 C1 C13 C5 1.99(17) . . . . ? C2 C1 C13 C12 -174.24(10) . . . . ? O1 C12 C13 C5 -107.89(12) . . . . ? C15 C12 C13 C5 10.92(15) . . . . ? O1 C12 C13 C1 68.21(12) . . . . ? C15 C12 C13 C1 -172.98(10) . . . . ? O2 C6 C14 C15 -107.92(10) . . . . ? C5 C6 C14 C15 11.12(14) . . . . ? O2 C6 C14 C8 9.39(11) . . . . ? C5 C6 C14 C8 128.43(10) . . . . ? C9 C8 C14 C6 -104.14(10) . . . . ? C7 C8 C14 C6 13.29(11) . . . . ? C9 C8 C14 C15 21.23(11) . . . . ? C7 C8 C14 C15 138.66(9) . . . . ? O1 C12 C15 C14 108.51(10) . . . . ? C13 C12 C15 C14 -10.09(14) . . . . ? O1 C12 C15 C10 -9.17(11) . . . . ? C13 C12 C15 C10 -127.76(10) . . . . ? C6 C14 C15 C12 -0.68(14) . . . . ? C8 C14 C15 C12 -116.71(10) . . . . ? C6 C14 C15 C10 115.74(10) . . . . ? C8 C14 C15 C10 -0.29(11) . . . . ? C11 C10 C15 C12 -12.69(11) . . . . ? C9 C10 C15 C12 104.62(10) . . . . ? C11 C10 C15 C14 -138.00(9) . . . . ? C9 C10 C15 C14 -20.69(12) . . . . ? O2 C7 C16 N2 50(18) . . . . ? C8 C7 C16 N2 -67(18) . . . . ? O1 C11 C17 N1 -179(100) . . . . ? C10 C11 C17 N1 -62(18) . . . . ? C17 C11 O1 C12 83.54(12) . . . . ? C10 C11 O1 C12 -38.35(12) . . . . ? C13 C12 O1 C11 156.81(9) . . . . ? C15 C12 O1 C11 29.87(11) . . . . ? C16 C7 O2 C6 -81.86(11) . . . . ? C8 C7 O2 C6 39.76(12) . . . . ? C5 C6 O2 C7 -157.89(9) . . . . ? C14 C6 O2 C7 -30.89(12) . . . . ? _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.209 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 942153'