# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2010src1081a #TrackingRef 'web_deposit_cif_file_0_GrahamJ.Tizzard_1355313337.2010src1081a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N8, 2(F6 P)' _chemical_formula_sum 'C16 H22 F12 N8 P2' _chemical_formula_weight 616.36 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9534(6) _cell_length_b 12.4354(3) _cell_length_c 15.5327(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.439(2) _cell_angle_gamma 90.00 _cell_volume 2468.14(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15697 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9026 _exptl_absorpt_correction_T_max 0.9550 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6621 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26765 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4343 _reflns_number_gt 2858 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0964P)^2^+5.0770P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4343 _refine_ls_number_parameters 410 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2144 _refine_ls_wR_factor_gt 0.1850 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _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 1.0328(3) 0.8036(3) -0.0547(3) 0.0389(10) Uani 1 1 d . . . H1 H 1.0582 0.8336 0.0010 0.047 Uiso 1 1 calc R . . C2 C 1.0005(4) 0.7767(4) -0.1970(3) 0.0531(13) Uani 1 1 d . . . H2 H 1.0000 0.7861 -0.2578 0.064 Uiso 1 1 calc R . . C3 C 0.9542(4) 0.6971(4) -0.1592(3) 0.0503(13) Uani 1 1 d . . . H3 H 0.9149 0.6394 -0.1883 0.060 Uiso 1 1 calc R . . C4 C 1.1101(4) 0.9397(4) -0.1424(4) 0.0561(14) Uani 1 1 d . . . H4A H 1.1401 0.9688 -0.0851 0.084 Uiso 1 1 calc R . . H4B H 1.0644 0.9936 -0.1751 0.084 Uiso 1 1 calc R . . H4C H 1.1667 0.9213 -0.1746 0.084 Uiso 1 1 calc R . . C5 C 0.9449(3) 0.6469(3) -0.0045(3) 0.0346(10) Uani 1 1 d . . . C6 C 0.8548(3) 0.5060(3) 0.0322(3) 0.0388(11) Uani 1 1 d . . . C7 C 0.9560(3) 0.6033(3) 0.1328(3) 0.0349(10) Uani 1 1 d . . . C8 C 0.7340(4) 0.4075(4) -0.0794(3) 0.0535(13) Uani 1 1 d . . . H8A H 0.7428 0.3324 -0.0981 0.064 Uiso 1 1 calc R . . H8B H 0.7630 0.4560 -0.1200 0.064 Uiso 1 1 calc R . . C9 C 0.6189(4) 0.4315(5) -0.0817(4) 0.0596(14) Uani 1 1 d . . . H9B H 0.5801 0.4157 -0.1407 0.071 Uiso 1 1 calc R . . H9A H 0.6100 0.5088 -0.0698 0.071 Uiso 1 1 calc R . . C10 C 0.5738(4) 0.3646(5) -0.0144(4) 0.0642(15) Uani 1 1 d . . . H10A H 0.5002 0.3859 -0.0143 0.077 Uiso 1 1 calc R . . H10B H 0.5746 0.2876 -0.0305 0.077 Uiso 1 1 calc R . . C11 C 0.6363(4) 0.3804(4) 0.0758(4) 0.0558(14) Uani 1 1 d . . . H11B H 0.6092 0.3319 0.1175 0.067 Uiso 1 1 calc R . . H11A H 0.6282 0.4554 0.0950 0.067 Uiso 1 1 calc R . . C12 C 0.7513(4) 0.3567(4) 0.0762(4) 0.0516(13) Uani 1 1 d . . . H12A H 0.7919 0.3728 0.1345 0.062 Uiso 1 1 calc R . . H12B H 0.7606 0.2797 0.0636 0.062 Uiso 1 1 calc R . . N1 N 1.0490(3) 0.8426(3) -0.1308(3) 0.0465(10) Uani 1 1 d . . . N2 N 0.9742(3) 0.7142(3) -0.0702(2) 0.0377(9) Uani 1 1 d . . . N3 N 0.8795(3) 0.5697(3) -0.0332(2) 0.0373(9) Uani 1 1 d . . . N4 N 0.8936(3) 0.5208(3) 0.1179(2) 0.0392(9) Uani 1 1 d . A . N5 N 0.9885(3) 0.6713(3) 0.0765(2) 0.0346(8) Uani 1 1 d . A . N6 N 0.7898(3) 0.4233(3) 0.0097(3) 0.0444(10) Uani 1 1 d . . . C13A C 1.0716(14) 0.6998(12) 0.2488(7) 0.032(3) Uani 0.647(8) 1 d PD A 1 H13A H 1.1044 0.7469 0.2134 0.039 Uiso 0.647(8) 1 calc PR A 1 C14A C 0.9701(19) 0.5744(18) 0.2921(11) 0.043(4) Uani 0.647(8) 1 d PD A 1 H14A H 0.9202 0.5182 0.2907 0.051 Uiso 0.647(8) 1 calc PR A 1 C15A C 1.0236(14) 0.6227(12) 0.3641(9) 0.041(4) Uani 0.647(8) 1 d PD A 1 H15A H 1.0191 0.6073 0.4233 0.049 Uiso 0.647(8) 1 calc PR A 1 C16A C 1.1624(7) 0.7645(6) 0.3895(5) 0.0514(18) Uani 0.647(8) 1 d PD A 1 H16A H 1.2145 0.7178 0.4240 0.077 Uiso 0.647(8) 1 calc PR A 1 H16B H 1.1267 0.8072 0.4288 0.077 Uiso 0.647(8) 1 calc PR A 1 H16C H 1.1973 0.8127 0.3535 0.077 Uiso 0.647(8) 1 calc PR A 1 N7A N 1.0030(10) 0.624(2) 0.2205(7) 0.029(3) Uani 0.647(8) 1 d PD A 1 N8A N 1.0861(9) 0.6988(10) 0.3335(5) 0.037(2) Uani 0.647(8) 1 d PD A 1 C13B C 0.954(4) 0.568(3) 0.2904(18) 0.032(3) Uani 0.353(8) 1 d PD A 2 H13B H 0.9062 0.5096 0.2847 0.039 Uiso 0.353(8) 1 calc PR A 2 C14B C 1.054(3) 0.702(3) 0.2598(17) 0.043(4) Uani 0.353(8) 1 d PD A 2 H14B H 1.0876 0.7532 0.2280 0.051 Uiso 0.353(8) 1 calc PR A 2 C15B C 1.068(2) 0.690(3) 0.3477(13) 0.041(4) Uani 0.353(8) 1 d PD A 2 H15B H 1.1116 0.7314 0.3901 0.049 Uiso 0.353(8) 1 calc PR A 2 C16B C 0.9981(13) 0.5661(11) 0.4503(8) 0.0514(18) Uani 0.353(8) 1 d PD A 2 H16D H 0.9716 0.6237 0.4839 0.077 Uiso 0.353(8) 1 calc PR A 2 H16E H 1.0677 0.5440 0.4797 0.077 Uiso 0.353(8) 1 calc PR A 2 H16F H 0.9504 0.5045 0.4462 0.077 Uiso 0.353(8) 1 calc PR A 2 N7B N 0.980(2) 0.625(4) 0.2256(14) 0.029(3) Uani 0.353(8) 1 d PD A 2 N8B N 1.005(3) 0.605(2) 0.3632(14) 0.037(2) Uani 0.353(8) 1 d PD A 2 F1A F 0.1941(3) 1.0979(3) 0.1733(3) 0.0706(13) Uani 0.812(4) 1 d PD B 1 F2A F 0.2104(4) 0.8478(3) 0.1389(4) 0.0833(16) Uani 0.812(4) 1 d PD B 1 F3A F 0.0988(3) 0.9777(4) 0.0857(3) 0.0705(13) Uani 0.812(4) 1 d PD B 1 F4A F 0.2716(3) 0.9951(4) 0.0826(2) 0.0745(13) Uani 0.812(4) 1 d PD B 1 F5A F 0.3076(3) 0.9736(4) 0.2272(3) 0.0669(12) Uani 0.812(4) 1 d PD B 1 F6A F 0.1344(4) 0.9505(4) 0.2305(3) 0.0674(12) Uani 0.812(4) 1 d PD B 1 P1A P 0.20422(19) 0.97372(16) 0.15636(16) 0.0397(5) Uani 0.812(4) 1 d PD B 1 F1B F 0.2028(14) 1.0673(11) 0.1169(13) 0.0706(13) Uani 0.188(4) 1 d PD B 2 F4B F 0.2550(13) 0.9067(16) 0.0665(9) 0.0745(13) Uani 0.188(4) 1 d PD B 2 F5B F 0.3390(11) 0.9720(17) 0.1907(12) 0.0669(12) Uani 0.188(4) 1 d PD B 2 F6B F 0.1776(15) 0.9897(15) 0.2372(11) 0.0674(12) Uani 0.188(4) 1 d PD B 2 F3B F 0.1065(11) 0.9118(16) 0.1156(12) 0.0705(13) Uani 0.188(4) 1 d PD B 2 F2B F 0.2435(16) 0.8338(11) 0.1989(15) 0.0833(16) Uani 0.188(4) 1 d PD B 2 P1B P 0.2231(9) 0.9480(9) 0.1533(8) 0.0397(5) Uani 0.188(4) 1 d PD B 2 F7A F 0.7277(8) 0.6990(6) 0.0861(6) 0.095(2) Uani 0.770(3) 1 d PD C 1 F8A F 0.7162(6) 0.8961(5) 0.2133(4) 0.083(2) Uani 0.770(3) 1 d PD C 1 F9A F 0.5953(3) 0.7918(4) 0.1307(3) 0.0815(14) Uani 0.770(3) 1 d PD C 1 F10A F 0.7258(4) 0.7181(4) 0.2293(3) 0.0936(16) Uani 0.770(3) 1 d PD C 1 F11A F 0.8429(3) 0.8040(3) 0.1689(3) 0.0676(11) Uani 0.770(3) 1 d PD C 1 F12A F 0.7165(5) 0.8796(4) 0.0723(3) 0.0919(16) Uani 0.770(3) 1 d PD C 1 P2A P 0.7191(3) 0.7968(4) 0.1491(3) 0.0435(7) Uani 0.770(3) 1 d PD C 1 F7B F 0.707(3) 0.677(2) 0.087(2) 0.095(2) Uani 0.230(3) 1 d PD C 2 F8B F 0.722(2) 0.9001(18) 0.1845(16) 0.083(2) Uani 0.230(3) 1 d PD C 2 F9B F 0.6307(10) 0.7522(14) 0.1963(10) 0.0815(14) Uani 0.230(3) 1 d PD C 2 F10B F 0.8073(14) 0.7421(14) 0.2098(10) 0.0936(16) Uani 0.230(3) 1 d PD C 2 F11B F 0.7991(10) 0.8252(11) 0.0829(9) 0.0676(11) Uani 0.230(3) 1 d PD C 2 F12B F 0.6258(13) 0.8331(13) 0.0670(10) 0.0919(16) Uani 0.230(3) 1 d PD C 2 P2B P 0.7152(12) 0.7862(15) 0.1391(10) 0.0435(7) Uani 0.230(3) 1 d PD C 2 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 0.041(3) 0.039(2) 0.037(2) 0.000(2) 0.008(2) 0.001(2) C2 0.071(4) 0.052(3) 0.035(3) 0.001(2) 0.003(2) 0.001(3) C3 0.067(3) 0.047(3) 0.035(3) -0.005(2) 0.001(2) 0.001(2) C4 0.065(4) 0.049(3) 0.058(3) 0.009(2) 0.020(3) -0.009(3) C5 0.034(2) 0.035(2) 0.036(2) -0.0023(19) 0.0091(19) 0.0054(19) C6 0.031(2) 0.036(2) 0.050(3) -0.007(2) 0.007(2) 0.0041(19) C7 0.032(2) 0.035(2) 0.038(2) -0.0001(19) 0.0069(19) 0.0036(19) C8 0.057(3) 0.041(3) 0.061(3) -0.016(2) 0.006(3) -0.008(2) C9 0.050(3) 0.059(3) 0.064(4) -0.003(3) -0.005(3) -0.010(3) C10 0.045(3) 0.066(4) 0.078(4) 0.000(3) -0.002(3) -0.014(3) C11 0.049(3) 0.051(3) 0.068(4) 0.005(3) 0.012(3) -0.008(2) C12 0.045(3) 0.040(3) 0.068(3) 0.003(2) 0.006(2) -0.005(2) N1 0.054(3) 0.044(2) 0.043(2) 0.0053(19) 0.0116(19) 0.0044(19) N2 0.041(2) 0.038(2) 0.034(2) -0.0016(16) 0.0074(16) 0.0019(17) N3 0.039(2) 0.0339(19) 0.039(2) -0.0043(16) 0.0075(17) -0.0017(17) N4 0.034(2) 0.038(2) 0.045(2) -0.0018(17) 0.0068(17) 0.0005(17) N5 0.0314(19) 0.0370(19) 0.035(2) 0.0005(16) 0.0054(16) 0.0020(16) N6 0.042(2) 0.043(2) 0.049(2) -0.0040(18) 0.0071(18) -0.0067(18) C13A 0.031(7) 0.036(4) 0.031(5) 0.004(4) 0.007(3) 0.003(4) C14A 0.032(8) 0.048(6) 0.049(6) 0.012(5) 0.010(5) -0.007(5) C15A 0.047(9) 0.045(8) 0.031(4) 0.002(4) 0.007(4) -0.008(5) C16A 0.071(5) 0.045(4) 0.034(4) 0.001(3) -0.002(3) -0.001(3) N7A 0.013(7) 0.036(2) 0.040(2) 0.001(2) 0.013(3) 0.002(6) N8A 0.043(5) 0.029(3) 0.042(5) 0.007(3) 0.012(3) -0.001(3) C13B 0.031(7) 0.036(4) 0.031(5) 0.004(4) 0.007(3) 0.003(4) C14B 0.032(8) 0.048(6) 0.049(6) 0.012(5) 0.010(5) -0.007(5) C15B 0.047(9) 0.045(8) 0.031(4) 0.002(4) 0.007(4) -0.008(5) C16B 0.071(5) 0.045(4) 0.034(4) 0.001(3) -0.002(3) -0.001(3) N7B 0.013(7) 0.036(2) 0.040(2) 0.001(2) 0.013(3) 0.002(6) N8B 0.043(5) 0.029(3) 0.042(5) 0.007(3) 0.012(3) -0.001(3) F1A 0.069(2) 0.033(2) 0.105(4) -0.007(2) -0.001(3) 0.0023(17) F2A 0.081(3) 0.036(2) 0.139(5) -0.017(3) 0.038(3) -0.004(2) F3A 0.057(2) 0.087(3) 0.060(3) -0.018(2) -0.0123(19) 0.002(2) F4A 0.073(3) 0.106(4) 0.048(2) -0.006(2) 0.0205(19) -0.030(3) F5A 0.059(3) 0.089(3) 0.047(3) 0.005(2) -0.0096(19) 0.015(2) F6A 0.074(3) 0.073(3) 0.061(2) 0.001(2) 0.028(2) -0.016(2) P1A 0.0465(12) 0.0302(13) 0.0407(8) -0.0041(8) 0.0026(8) -0.0001(8) F1B 0.069(2) 0.033(2) 0.105(4) -0.007(2) -0.001(3) 0.0023(17) F4B 0.073(3) 0.106(4) 0.048(2) -0.006(2) 0.0205(19) -0.030(3) F5B 0.059(3) 0.089(3) 0.047(3) 0.005(2) -0.0096(19) 0.015(2) F6B 0.074(3) 0.073(3) 0.061(2) 0.001(2) 0.028(2) -0.016(2) F3B 0.057(2) 0.087(3) 0.060(3) -0.018(2) -0.0123(19) 0.002(2) F2B 0.081(3) 0.036(2) 0.139(5) -0.017(3) 0.038(3) -0.004(2) P1B 0.0465(12) 0.0302(13) 0.0407(8) -0.0041(8) 0.0026(8) -0.0001(8) F7A 0.106(5) 0.087(4) 0.087(3) -0.044(3) -0.001(3) 0.021(3) F8A 0.076(3) 0.097(3) 0.069(5) -0.040(3) -0.005(3) 0.032(2) F9A 0.046(2) 0.105(4) 0.087(3) 0.004(3) -0.007(2) 0.008(2) F10A 0.108(4) 0.094(3) 0.078(3) 0.046(3) 0.013(3) -0.005(3) F11A 0.044(2) 0.072(3) 0.089(3) -0.002(2) 0.018(2) 0.0091(19) F12A 0.113(4) 0.082(3) 0.075(3) 0.036(3) -0.001(3) -0.005(3) P2A 0.0482(9) 0.0473(13) 0.0348(13) -0.0027(10) 0.0066(8) 0.0128(8) F7B 0.106(5) 0.087(4) 0.087(3) -0.044(3) -0.001(3) 0.021(3) F8B 0.076(3) 0.097(3) 0.069(5) -0.040(3) -0.005(3) 0.032(2) F9B 0.046(2) 0.105(4) 0.087(3) 0.004(3) -0.007(2) 0.008(2) F10B 0.108(4) 0.094(3) 0.078(3) 0.046(3) 0.013(3) -0.005(3) F11B 0.044(2) 0.072(3) 0.089(3) -0.002(2) 0.018(2) 0.0091(19) F12B 0.113(4) 0.082(3) 0.075(3) 0.036(3) -0.001(3) -0.005(3) P2B 0.0482(9) 0.0473(13) 0.0348(13) -0.0027(10) 0.0066(8) 0.0128(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.326(6) . ? C1 N2 1.345(6) . ? C1 H1 0.9500 . ? C2 C3 1.343(7) . ? C2 N1 1.382(6) . ? C2 H2 0.9500 . ? C3 N2 1.381(6) . ? C3 H3 0.9500 . ? C4 N1 1.471(6) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.308(6) . ? C5 N5 1.328(5) . ? C5 N2 1.419(5) . ? C6 N6 1.339(6) . ? C6 N4 1.355(6) . ? C6 N3 1.367(6) . ? C7 N4 1.304(5) . ? C7 N5 1.333(5) . ? C7 N7A 1.420(11) . ? C7 N7B 1.45(2) . ? C8 N6 1.466(6) . ? C8 C9 1.515(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.525(8) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C10 C11 1.513(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.517(7) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C12 N6 1.473(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13A N8A 1.298(13) . ? C13A N7A 1.325(18) . ? C13A H13A 0.9500 . ? C14A C15A 1.356(16) . ? C14A N7A 1.395(19) . ? C14A H14A 0.9500 . ? C15A N8A 1.379(10) . ? C15A H15A 0.9500 . ? C16A N8A 1.456(16) . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C13B N8B 1.30(2) . ? C13B N7B 1.32(3) . ? C13B H13B 0.9500 . ? C14B C15B 1.36(2) . ? C14B N7B 1.40(3) . ? C14B H14B 0.9500 . ? C15B N8B 1.374(16) . ? C15B H15B 0.9500 . ? C16B N8B 1.45(2) . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? F1A P1A 1.576(4) . ? F2A P1A 1.594(4) . ? F3A P1A 1.606(4) . ? F4A P1A 1.572(4) . ? F5A P1A 1.587(4) . ? F6A P1A 1.603(4) . ? F1B P1B 1.594(13) . ? F4B P1B 1.562(14) . ? F5B P1B 1.547(14) . ? F6B P1B 1.602(14) . ? F3B P1B 1.594(14) . ? F2B P1B 1.589(15) . ? F7A P2A 1.576(5) . ? F8A P2A 1.591(5) . ? F9A P2A 1.583(6) . ? F10A P2A 1.575(6) . ? F11A P2A 1.585(6) . ? F12A P2A 1.572(6) . ? F7B P2B 1.568(15) . ? F8B P2B 1.579(15) . ? F9B P2B 1.576(15) . ? F10B P2B 1.581(15) . ? F11B P2B 1.578(15) . ? F12B P2B 1.584(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 108.0(4) . . ? N1 C1 H1 126.0 . . ? N2 C1 H1 126.0 . . ? C3 C2 N1 107.0(4) . . ? C3 C2 H2 126.5 . . ? N1 C2 H2 126.5 . . ? C2 C3 N2 107.5(4) . . ? C2 C3 H3 126.3 . . ? N2 C3 H3 126.3 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N5 129.8(4) . . ? N3 C5 N2 115.0(4) . . ? N5 C5 N2 115.1(4) . . ? N6 C6 N4 118.5(4) . . ? N6 C6 N3 117.7(4) . . ? N4 C6 N3 123.8(4) . . ? N4 C7 N5 129.5(4) . . ? N4 C7 N7A 117.8(9) . . ? N5 C7 N7A 112.7(9) . . ? N4 C7 N7B 110.4(16) . . ? N5 C7 N7B 119.7(17) . . ? N7A C7 N7B 12.8(17) . . ? N6 C8 C9 109.1(4) . . ? N6 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? N6 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C8 C9 C10 111.3(5) . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? H9B C9 H9A 108.0 . . ? C11 C10 C9 110.9(4) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 110.8(5) . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? H11B C11 H11A 108.1 . . ? N6 C12 C11 109.5(4) . . ? N6 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? N6 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C1 N1 C2 109.2(4) . . ? C1 N1 C4 125.1(4) . . ? C2 N1 C4 125.7(4) . . ? C1 N2 C3 108.3(4) . . ? C1 N2 C5 124.7(4) . . ? C3 N2 C5 126.8(4) . . ? C5 N3 C6 112.9(4) . . ? C7 N4 C6 113.6(4) . . ? C5 N5 C7 110.3(4) . . ? C6 N6 C8 122.8(4) . . ? C6 N6 C12 121.3(4) . . ? C8 N6 C12 114.5(4) . . ? N8A C13A N7A 107.9(11) . . ? N8A C13A H13A 126.1 . . ? N7A C13A H13A 126.1 . . ? C15A C14A N7A 106.4(12) . . ? C15A C14A H14A 126.8 . . ? N7A C14A H14A 126.8 . . ? C14A C15A N8A 105.6(14) . . ? C14A C15A H15A 127.2 . . ? N8A C15A H15A 127.2 . . ? C13A N7A C14A 109.0(8) . . ? C13A N7A C7 127.1(14) . . ? C14A N7A C7 123.2(13) . . ? C13A N8A C15A 111.2(13) . . ? C13A N8A C16A 124.9(11) . . ? C15A N8A C16A 123.9(8) . . ? N8B C13B N7B 108(2) . . ? N8B C13B H13B 125.8 . . ? N7B C13B H13B 125.8 . . ? C15B C14B N7B 106(2) . . ? C15B C14B H14B 127.2 . . ? N7B C14B H14B 127.2 . . ? C14B C15B N8B 106(2) . . ? C14B C15B H15B 126.8 . . ? N8B C15B H15B 126.8 . . ? N8B C16B H16D 109.5 . . ? N8B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? N8B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C13B N7B C14B 108.9(14) . . ? C13B N7B C7 128(3) . . ? C14B N7B C7 122(2) . . ? C13B N8B C15B 111(2) . . ? C13B N8B C16B 126(2) . . ? C15B N8B C16B 123.1(16) . . ? F4A P1A F1A 91.6(3) . . ? F4A P1A F5A 89.9(3) . . ? F1A P1A F5A 88.2(2) . . ? F4A P1A F2A 89.6(3) . . ? F1A P1A F2A 178.1(3) . . ? F5A P1A F2A 93.2(3) . . ? F4A P1A F6A 179.1(3) . . ? F1A P1A F6A 89.1(3) . . ? F5A P1A F6A 90.7(3) . . ? F2A P1A F6A 89.7(3) . . ? F4A P1A F3A 90.5(3) . . ? F1A P1A F3A 89.9(2) . . ? F5A P1A F3A 178.1(3) . . ? F2A P1A F3A 88.6(3) . . ? F6A P1A F3A 88.8(3) . . ? F5B P1B F4B 90.6(11) . . ? F5B P1B F2B 85.7(11) . . ? F4B P1B F2B 92.5(11) . . ? F5B P1B F3B 174.7(12) . . ? F4B P1B F3B 87.6(10) . . ? F2B P1B F3B 89.4(11) . . ? F5B P1B F1B 92.7(11) . . ? F4B P1B F1B 92.9(11) . . ? F2B P1B F1B 174.4(13) . . ? F3B P1B F1B 92.3(11) . . ? F5B P1B F6B 95.5(11) . . ? F4B P1B F6B 173.8(12) . . ? F2B P1B F6B 89.1(11) . . ? F3B P1B F6B 86.4(10) . . ? F1B P1B F6B 85.7(11) . . ? F12A P2A F10A 176.9(4) . . ? F12A P2A F7A 91.7(5) . . ? F10A P2A F7A 90.6(5) . . ? F12A P2A F9A 89.6(4) . . ? F10A P2A F9A 92.4(4) . . ? F7A P2A F9A 91.7(4) . . ? F12A P2A F11A 90.3(4) . . ? F10A P2A F11A 87.7(3) . . ? F7A P2A F11A 89.5(4) . . ? F9A P2A F11A 178.7(4) . . ? F12A P2A F8A 88.1(4) . . ? F10A P2A F8A 89.5(4) . . ? F7A P2A F8A 177.3(5) . . ? F9A P2A F8A 90.9(4) . . ? F11A P2A F8A 87.8(4) . . ? F7B P2B F9B 93.7(16) . . ? F7B P2B F11B 88.5(15) . . ? F9B P2B F11B 177.6(15) . . ? F7B P2B F8B 175.8(18) . . ? F9B P2B F8B 89.0(14) . . ? F11B P2B F8B 88.7(13) . . ? F7B P2B F10B 91.9(15) . . ? F9B P2B F10B 91.7(11) . . ? F11B P2B F10B 88.9(11) . . ? F8B P2B F10B 91.1(14) . . ? F7B P2B F12B 88.7(15) . . ? F9B P2B F12B 90.2(11) . . ? F11B P2B F12B 89.1(11) . . ? F8B P2B F12B 88.1(13) . . ? F10B P2B F12B 177.9(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 0.1(6) . . . . ? N6 C8 C9 C10 -54.8(6) . . . . ? C8 C9 C10 C11 54.8(6) . . . . ? C9 C10 C11 C12 -54.7(6) . . . . ? C10 C11 C12 N6 55.1(6) . . . . ? N2 C1 N1 C2 -0.4(5) . . . . ? N2 C1 N1 C4 -179.6(4) . . . . ? C3 C2 N1 C1 0.2(6) . . . . ? C3 C2 N1 C4 179.4(5) . . . . ? N1 C1 N2 C3 0.5(5) . . . . ? N1 C1 N2 C5 176.8(4) . . . . ? C2 C3 N2 C1 -0.3(6) . . . . ? C2 C3 N2 C5 -176.6(4) . . . . ? N3 C5 N2 C1 173.8(4) . . . . ? N5 C5 N2 C1 -6.7(6) . . . . ? N3 C5 N2 C3 -10.6(6) . . . . ? N5 C5 N2 C3 169.0(4) . . . . ? N5 C5 N3 C6 -0.4(6) . . . . ? N2 C5 N3 C6 179.0(3) . . . . ? N6 C6 N3 C5 -178.8(4) . . . . ? N4 C6 N3 C5 0.0(6) . . . . ? N5 C7 N4 C6 -2.3(6) . . . . ? N7A C7 N4 C6 -178.2(9) . . . . ? N7B C7 N4 C6 170.2(18) . . . . ? N6 C6 N4 C7 180.0(4) . . . . ? N3 C6 N4 C7 1.2(6) . . . . ? N3 C5 N5 C7 -0.4(6) . . . . ? N2 C5 N5 C7 -179.9(3) . . . . ? N4 C7 N5 C5 2.0(6) . . . . ? N7A C7 N5 C5 178.0(9) . . . . ? N7B C7 N5 C5 -170.0(18) . . . . ? N4 C6 N6 C8 172.6(4) . . . . ? N3 C6 N6 C8 -8.5(6) . . . . ? N4 C6 N6 C12 6.9(6) . . . . ? N3 C6 N6 C12 -174.2(4) . . . . ? C9 C8 N6 C6 -108.5(5) . . . . ? C9 C8 N6 C12 58.1(5) . . . . ? C11 C12 N6 C6 108.3(5) . . . . ? C11 C12 N6 C8 -58.4(5) . . . . ? N7A C14A C15A N8A 0(2) . . . . ? N8A C13A N7A C14A 2(3) . . . . ? N8A C13A N7A C7 172.9(14) . . . . ? C15A C14A N7A C13A -1(3) . . . . ? C15A C14A N7A C7 -172.6(17) . . . . ? N4 C7 N7A C13A 176.9(15) . . . . ? N5 C7 N7A C13A 0(2) . . . . ? N7B C7 N7A C13A -125(15) . . . . ? N4 C7 N7A C14A -14(3) . . . . ? N5 C7 N7A C14A 170(2) . . . . ? N7B C7 N7A C14A 44(12) . . . . ? N7A C13A N8A C15A -2.0(17) . . . . ? N7A C13A N8A C16A 174.6(13) . . . . ? C14A C15A N8A C13A 1.1(15) . . . . ? C14A C15A N8A C16A -175.5(17) . . . . ? N7B C14B C15B N8B 2(4) . . . . ? N8B C13B N7B C14B 1(6) . . . . ? N8B C13B N7B C7 169(3) . . . . ? C15B C14B N7B C13B -2(5) . . . . ? C15B C14B N7B C7 -171(3) . . . . ? N4 C7 N7B C13B 6(5) . . . . ? N5 C7 N7B C13B 180(4) . . . . ? N7A C7 N7B C13B -121(17) . . . . ? N4 C7 N7B C14B 173(3) . . . . ? N5 C7 N7B C14B -13(4) . . . . ? N7A C7 N7B C14B 46(10) . . . . ? N7B C13B N8B C15B 0(5) . . . . ? N7B C13B N8B C16B 179(4) . . . . ? C14B C15B N8B C13B -1(3) . . . . ? C14B C15B N8B C16B 180(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.800 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 915430' ####################################################################### # # 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_2010src1064a #TrackingRef 'web_deposit_cif_file_1_GrahamJ.Tizzard_1355313337.2010src1064a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H25 Ag Cl N7' _chemical_formula_sum 'C17 H25 Ag Cl N7' _chemical_formula_weight 470.76 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' Cl Cl 0.1484 0.1585 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.5255(10) _cell_length_b 12.8841(3) _cell_length_c 9.4379(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.935(2) _cell_angle_gamma 90.00 _cell_volume 3854.70(19) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 36249 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 1.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8129 _exptl_absorpt_correction_T_max 0.9535 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 20932 reflections reduced R(int) from 0.0894 to 0.0520 Ratio of minimum to maximum apparent transmission: 0.839179 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 66.065 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22599 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4416 _reflns_number_gt 3725 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+24.6902P] 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 4416 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.71547(11) 0.4785(3) 1.0804(4) 0.0227(7) Uani 1 1 d . . . C2 C 0.74882(12) 0.6146(3) 1.2062(4) 0.0282(8) Uani 1 1 d . . . H2 H 0.7677 0.6526 1.2792 0.034 Uiso 1 1 calc R . . C3 C 0.72072(12) 0.6541(3) 1.0928(4) 0.0288(8) Uani 1 1 d . . . H3 H 0.7157 0.7255 1.0698 0.035 Uiso 1 1 calc R . . C4 C 0.77049(12) 0.4364(3) 1.3010(4) 0.0279(8) Uani 1 1 d . . . H4A H 0.7542 0.3734 1.3085 0.042 Uiso 1 1 calc R . . H4B H 0.7783 0.4701 1.3964 0.042 Uiso 1 1 calc R . . H4C H 0.7961 0.4180 1.2683 0.042 Uiso 1 1 calc R . . C5 C 0.66765(11) 0.5812(3) 0.8869(4) 0.0207(7) Uani 1 1 d . . . C6 C 0.62463(11) 0.6885(3) 0.7382(4) 0.0201(7) Uani 1 1 d . . . C7 C 0.62141(10) 0.5148(3) 0.6997(3) 0.0184(7) Uani 1 1 d . . . C8 C 0.63036(13) 0.8771(3) 0.7826(4) 0.0304(9) Uani 1 1 d . . . H8A H 0.6430 0.9191 0.7156 0.036 Uiso 1 1 calc R . . H8B H 0.6532 0.8552 0.8651 0.036 Uiso 1 1 calc R . . C9 C 0.59836(14) 0.9417(3) 0.8382(5) 0.0358(10) Uani 1 1 d . . . H9A H 0.6121 1.0055 0.8847 0.043 Uiso 1 1 calc R . . H9B H 0.5879 0.9018 0.9127 0.043 Uiso 1 1 calc R . . C10 C 0.56147(14) 0.9711(3) 0.7157(6) 0.0443(11) Uani 1 1 d . . . H10A H 0.5712 1.0186 0.6475 0.053 Uiso 1 1 calc R . . H10B H 0.5399 1.0079 0.7558 0.053 Uiso 1 1 calc R . . C11 C 0.54214(13) 0.8737(3) 0.6344(5) 0.0384(10) Uani 1 1 d . . . H11A H 0.5287 0.8315 0.6991 0.046 Uiso 1 1 calc R . . H11B H 0.5199 0.8944 0.5491 0.046 Uiso 1 1 calc R . . C12 C 0.57490(12) 0.8088(3) 0.5838(4) 0.0254(8) Uani 1 1 d . . . H12A H 0.5619 0.7433 0.5404 0.030 Uiso 1 1 calc R . . H12B H 0.5856 0.8470 0.5085 0.030 Uiso 1 1 calc R . . C13 C 0.56740(11) 0.4396(3) 0.5017(4) 0.0227(7) Uani 1 1 d . . . H13A H 0.5719 0.4037 0.4136 0.027 Uiso 1 1 calc R . . H13B H 0.5611 0.5134 0.4770 0.027 Uiso 1 1 calc R . . C14 C 0.53021(12) 0.3900(3) 0.5514(4) 0.0280(8) Uani 1 1 d . . . H14A H 0.5235 0.4316 0.6314 0.034 Uiso 1 1 calc R . . H14B H 0.5051 0.3899 0.4697 0.034 Uiso 1 1 calc R . . C15 C 0.54046(12) 0.2788(3) 0.6035(5) 0.0315(9) Uani 1 1 d . . . H15A H 0.5172 0.2510 0.6442 0.038 Uiso 1 1 calc R . . H15B H 0.5430 0.2347 0.5200 0.038 Uiso 1 1 calc R . . C16 C 0.58149(12) 0.2747(3) 0.7191(4) 0.0285(8) Uani 1 1 d . . . H16A H 0.5778 0.3113 0.8077 0.034 Uiso 1 1 calc R . . H16B H 0.5889 0.2016 0.7453 0.034 Uiso 1 1 calc R . . C17 C 0.61687(11) 0.3254(3) 0.6627(4) 0.0225(7) Uani 1 1 d . . . H17A H 0.6431 0.3253 0.7399 0.027 Uiso 1 1 calc R . . H17B H 0.6222 0.2853 0.5791 0.027 Uiso 1 1 calc R . . N1 N 0.74488(9) 0.5078(2) 1.1962(3) 0.0235(6) Uani 1 1 d . . . N2 N 0.70030(9) 0.5695(2) 1.0156(3) 0.0222(6) Uani 1 1 d . . . N3 N 0.65720(9) 0.6783(2) 0.8557(3) 0.0225(6) Uani 1 1 d . . . N4 N 0.60566(9) 0.6090(2) 0.6566(3) 0.0196(6) Uani 1 1 d . . . N5 N 0.65286(9) 0.4955(2) 0.8186(3) 0.0198(6) Uani 1 1 d . . . N6 N 0.60975(10) 0.7854(2) 0.7063(3) 0.0252(7) Uani 1 1 d . . . N7 N 0.60549(9) 0.4319(2) 0.6176(3) 0.0218(6) Uani 1 1 d . . . Cl1 Cl 0.67602(3) 0.15746(7) 0.95725(10) 0.0282(2) Uani 1 1 d . . . Ag1 Ag 0.695858(9) 0.32967(2) 1.01226(3) 0.02375(9) 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 0.0194(17) 0.0247(17) 0.0236(17) -0.0014(14) 0.0042(14) -0.0013(14) C2 0.0265(19) 0.0250(18) 0.030(2) -0.0049(15) 0.0003(16) -0.0051(15) C3 0.030(2) 0.0225(18) 0.031(2) -0.0055(15) 0.0014(16) -0.0093(15) C4 0.0245(19) 0.033(2) 0.0237(18) 0.0014(16) -0.0005(15) 0.0028(16) C5 0.0228(18) 0.0237(17) 0.0166(15) -0.0018(13) 0.0067(13) -0.0022(14) C6 0.0237(17) 0.0183(16) 0.0198(16) -0.0011(13) 0.0084(14) -0.0006(13) C7 0.0202(16) 0.0204(16) 0.0159(15) -0.0010(13) 0.0066(13) -0.0027(13) C8 0.038(2) 0.0172(17) 0.033(2) -0.0030(15) 0.0017(17) -0.0055(16) C9 0.050(3) 0.0232(19) 0.038(2) -0.0112(17) 0.019(2) -0.0120(18) C10 0.036(2) 0.026(2) 0.072(3) -0.020(2) 0.014(2) 0.0028(18) C11 0.033(2) 0.028(2) 0.056(3) -0.0117(19) 0.014(2) -0.0020(17) C12 0.031(2) 0.0200(17) 0.0230(18) -0.0003(14) 0.0007(15) 0.0010(14) C13 0.0250(18) 0.0217(17) 0.0198(16) -0.0018(14) 0.0017(14) 0.0010(14) C14 0.028(2) 0.0234(18) 0.033(2) -0.0020(15) 0.0075(16) 0.0010(15) C15 0.026(2) 0.0249(19) 0.044(2) 0.0037(17) 0.0092(17) -0.0059(16) C16 0.039(2) 0.0188(17) 0.0279(19) 0.0035(15) 0.0077(17) -0.0017(16) C17 0.0267(18) 0.0175(16) 0.0201(16) -0.0002(14) -0.0013(14) 0.0005(14) N1 0.0224(15) 0.0241(15) 0.0222(15) -0.0022(12) 0.0017(12) -0.0020(12) N2 0.0262(16) 0.0184(14) 0.0217(14) -0.0025(12) 0.0046(12) -0.0021(12) N3 0.0267(15) 0.0182(14) 0.0218(14) -0.0003(12) 0.0034(12) -0.0026(12) N4 0.0220(15) 0.0162(13) 0.0216(14) -0.0021(11) 0.0068(12) -0.0014(11) N5 0.0210(14) 0.0186(14) 0.0189(14) -0.0029(11) 0.0024(11) -0.0019(12) N6 0.0344(18) 0.0158(14) 0.0242(15) -0.0001(12) 0.0042(13) -0.0017(12) N7 0.0258(16) 0.0162(13) 0.0216(14) -0.0032(11) 0.0011(12) -0.0001(12) Cl1 0.0310(5) 0.0238(4) 0.0278(4) -0.0015(4) 0.0023(4) -0.0007(4) Ag1 0.02741(15) 0.01988(14) 0.02267(14) -0.00079(11) 0.00289(10) -0.00113(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.335(4) . ? C1 N2 1.363(4) . ? C1 Ag1 2.078(4) . ? C2 C3 1.343(5) . ? C2 N1 1.384(5) . ? C2 H2 0.9500 . ? C3 N2 1.394(4) . ? C3 H3 0.9500 . ? C4 N1 1.466(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.312(4) . ? C5 N5 1.314(4) . ? C5 N2 1.431(4) . ? C6 N4 1.345(4) . ? C6 N6 1.349(4) . ? C6 N3 1.358(4) . ? C7 N4 1.345(4) . ? C7 N7 1.352(4) . ? C7 N5 1.362(4) . ? C8 N6 1.465(4) . ? C8 C9 1.516(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.517(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.531(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.514(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N6 1.458(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N7 1.461(4) . ? C13 C14 1.531(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.527(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.524(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.520(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N7 1.460(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? Cl1 Ag1 2.3364(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 104.2(3) . . ? N1 C1 Ag1 128.9(3) . . ? N2 C1 Ag1 126.9(2) . . ? C3 C2 N1 106.7(3) . . ? C3 C2 H2 126.7 . . ? N1 C2 H2 126.7 . . ? C2 C3 N2 106.2(3) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N5 130.0(3) . . ? N3 C5 N2 113.3(3) . . ? N5 C5 N2 116.6(3) . . ? N4 C6 N6 118.8(3) . . ? N4 C6 N3 124.6(3) . . ? N6 C6 N3 116.5(3) . . ? N4 C7 N7 118.0(3) . . ? N4 C7 N5 125.4(3) . . ? N7 C7 N5 116.7(3) . . ? N6 C8 C9 109.8(3) . . ? N6 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N6 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C10 111.1(3) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 110.1(4) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 111.9(3) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N6 C12 C11 110.0(3) . . ? N6 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? N6 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N7 C13 C14 109.7(3) . . ? N7 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? N7 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 111.1(3) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C14 110.9(3) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 110.2(3) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N7 C17 C16 110.1(3) . . ? N7 C17 H17A 109.6 . . ? C16 C17 H17A 109.6 . . ? N7 C17 H17B 109.6 . . ? C16 C17 H17B 109.6 . . ? H17A C17 H17B 108.2 . . ? C1 N1 C2 112.0(3) . . ? C1 N1 C4 124.8(3) . . ? C2 N1 C4 123.2(3) . . ? C1 N2 C3 110.8(3) . . ? C1 N2 C5 126.7(3) . . ? C3 N2 C5 122.5(3) . . ? C5 N3 C6 113.0(3) . . ? C7 N4 C6 114.8(3) . . ? C5 N5 C7 112.1(3) . . ? C6 N6 C12 123.0(3) . . ? C6 N6 C8 122.3(3) . . ? C12 N6 C8 114.3(3) . . ? C7 N7 C17 122.4(3) . . ? C7 N7 C13 121.8(3) . . ? C17 N7 C13 113.5(3) . . ? C1 Ag1 Cl1 174.85(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 N1 C2 C3 N2 -0.2(4) . . . . ? N6 C8 C9 C10 -55.9(4) . . . . ? C8 C9 C10 C11 54.3(5) . . . . ? C9 C10 C11 C12 -53.5(5) . . . . ? C10 C11 C12 N6 53.8(5) . . . . ? N7 C13 C14 C15 -54.2(4) . . . . ? C13 C14 C15 C16 53.5(4) . . . . ? C14 C15 C16 C17 -54.4(4) . . . . ? C15 C16 C17 N7 56.7(4) . . . . ? N2 C1 N1 C2 -0.2(4) . . . . ? Ag1 C1 N1 C2 -179.5(3) . . . . ? N2 C1 N1 C4 -179.8(3) . . . . ? Ag1 C1 N1 C4 0.9(5) . . . . ? C3 C2 N1 C1 0.2(4) . . . . ? C3 C2 N1 C4 179.9(3) . . . . ? N1 C1 N2 C3 0.1(4) . . . . ? Ag1 C1 N2 C3 179.4(3) . . . . ? N1 C1 N2 C5 -179.4(3) . . . . ? Ag1 C1 N2 C5 0.0(5) . . . . ? C2 C3 N2 C1 0.1(4) . . . . ? C2 C3 N2 C5 179.5(3) . . . . ? N3 C5 N2 C1 174.9(3) . . . . ? N5 C5 N2 C1 -5.1(5) . . . . ? N3 C5 N2 C3 -4.4(5) . . . . ? N5 C5 N2 C3 175.6(3) . . . . ? N5 C5 N3 C6 3.5(5) . . . . ? N2 C5 N3 C6 -176.5(3) . . . . ? N4 C6 N3 C5 -2.7(5) . . . . ? N6 C6 N3 C5 174.8(3) . . . . ? N7 C7 N4 C6 -176.2(3) . . . . ? N5 C7 N4 C6 2.5(5) . . . . ? N6 C6 N4 C7 -177.4(3) . . . . ? N3 C6 N4 C7 0.0(5) . . . . ? N3 C5 N5 C7 -1.3(5) . . . . ? N2 C5 N5 C7 178.7(3) . . . . ? N4 C7 N5 C5 -2.0(5) . . . . ? N7 C7 N5 C5 176.8(3) . . . . ? N4 C6 N6 C12 -2.3(5) . . . . ? N3 C6 N6 C12 -179.9(3) . . . . ? N4 C6 N6 C8 -175.4(3) . . . . ? N3 C6 N6 C8 7.0(5) . . . . ? C11 C12 N6 C6 129.2(4) . . . . ? C11 C12 N6 C8 -57.1(4) . . . . ? C9 C8 N6 C6 -128.1(4) . . . . ? C9 C8 N6 C12 58.3(4) . . . . ? N4 C7 N7 C17 -173.0(3) . . . . ? N5 C7 N7 C17 8.1(5) . . . . ? N4 C7 N7 C13 -11.2(5) . . . . ? N5 C7 N7 C13 169.9(3) . . . . ? C16 C17 N7 C7 102.9(4) . . . . ? C16 C17 N7 C13 -60.3(4) . . . . ? C14 C13 N7 C7 -104.7(4) . . . . ? C14 C13 N7 C17 58.6(4) . . . . ? N1 C1 Ag1 Cl1 23.7(13) . . . . ? N2 C1 Ag1 Cl1 -155.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.533 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 915431' ####################################################################### # # 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_2011src0386a #TrackingRef 'web_deposit_cif_file_2_GrahamJ.Tizzard_1355313337.2011src0386a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H21 Ag Cl N7 O2' _chemical_formula_sum 'C15 H21 Ag Cl N7 O2' _chemical_formula_weight 474.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 6.9514(2) _cell_length_b 20.5662(3) _cell_length_c 12.5800(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.3100(10) _cell_angle_gamma 90.00 _cell_volume 1793.40(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11024 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9032 _exptl_absorpt_correction_T_max 0.9499 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6405 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21557 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4098 _reflns_number_gt 3384 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.7287P] 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 4098 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2894(4) 0.93580(15) -0.0917(2) 0.0164(6) Uani 1 1 d . . . C2 C 0.3464(4) 0.98270(15) -0.2490(2) 0.0174(6) Uani 1 1 d . . . H2 H 0.3722 0.9868 -0.3218 0.021 Uiso 1 1 calc R . . C3 C 0.3236(4) 1.03177(15) -0.1808(2) 0.0170(6) Uani 1 1 d . . . H3 H 0.3308 1.0770 -0.1952 0.020 Uiso 1 1 calc R . . C4 C 0.3395(5) 0.86037(15) -0.2425(3) 0.0222(7) Uani 1 1 d . . . H4A H 0.3075 0.8270 -0.1910 0.033 Uiso 1 1 calc R . . H4B H 0.4712 0.8534 -0.2629 0.033 Uiso 1 1 calc R . . H4C H 0.2490 0.8576 -0.3059 0.033 Uiso 1 1 calc R . . C5 C 0.2449(4) 1.03869(14) 0.0082(2) 0.0137(6) Uani 1 1 d . . . C6 C 0.1991(4) 1.13546(14) 0.0824(2) 0.0151(6) Uani 1 1 d . . . C7 C 0.1795(4) 1.04290(14) 0.1789(2) 0.0133(6) Uani 1 1 d . . . C8 C 0.2355(5) 1.23742(16) -0.0190(3) 0.0239(7) Uani 1 1 d . . . H8A H 0.1152 1.2517 -0.0595 0.029 Uiso 1 1 calc R . . H8B H 0.3089 1.2097 -0.0660 0.029 Uiso 1 1 calc R . . C9 C 0.3551(5) 1.29604(16) 0.0177(3) 0.0302(8) Uani 1 1 d . . . H9A H 0.4793 1.2810 0.0530 0.036 Uiso 1 1 calc R . . H9B H 0.3837 1.3223 -0.0452 0.036 Uiso 1 1 calc R . . C10 C 0.2257(5) 1.29899(16) 0.1839(3) 0.0279(8) Uani 1 1 d . . . H10A H 0.1613 1.3268 0.2347 0.033 Uiso 1 1 calc R . . H10B H 0.3510 1.2848 0.2189 0.033 Uiso 1 1 calc R . . C11 C 0.1019(5) 1.24020(15) 0.1566(3) 0.0233(7) Uani 1 1 d . . . H11A H 0.0888 1.2139 0.2216 0.028 Uiso 1 1 calc R . . H11B H -0.0285 1.2543 0.1290 0.028 Uiso 1 1 calc R . . C12 C 0.1205(5) 1.05016(15) 0.3692(2) 0.0177(7) Uani 1 1 d . . . H12A H -0.0155 1.0438 0.3853 0.021 Uiso 1 1 calc R . . H12B H 0.1413 1.0971 0.3572 0.021 Uiso 1 1 calc R . . C13 C 0.2526(5) 1.02708(15) 0.4615(2) 0.0190(7) Uani 1 1 d . . . H13A H 0.3874 1.0379 0.4480 0.023 Uiso 1 1 calc R . . H13B H 0.2209 1.0504 0.5269 0.023 Uiso 1 1 calc R . . C14 C 0.2794(5) 0.92256(15) 0.3850(3) 0.0190(7) Uani 1 1 d . . . H14A H 0.2622 0.8755 0.3979 0.023 Uiso 1 1 calc R . . H14B H 0.4158 0.9298 0.3705 0.023 Uiso 1 1 calc R . . C15 C 0.1498(5) 0.94292(14) 0.2882(3) 0.0184(7) Uani 1 1 d . . . H15A H 0.1913 0.9207 0.2239 0.022 Uiso 1 1 calc R . . H15B H 0.0152 0.9299 0.2979 0.022 Uiso 1 1 calc R . . N1 N 0.3255(4) 0.92496(12) -0.1940(2) 0.0158(5) Uani 1 1 d . . . N2 N 0.2871(3) 1.00258(12) -0.0841(2) 0.0139(5) Uani 1 1 d . . . N3 N 0.2426(4) 1.10240(12) -0.0061(2) 0.0160(5) Uani 1 1 d . . . N4 N 0.1678(4) 1.10788(12) 0.1766(2) 0.0152(5) Uani 1 1 d . . . N5 N 0.2148(4) 1.00438(11) 0.09427(19) 0.0142(5) Uani 1 1 d . . . N6 N 0.1895(4) 1.20064(12) 0.0760(2) 0.0203(6) Uani 1 1 d . . . N7 N 0.1592(4) 1.01360(12) 0.2735(2) 0.0158(5) Uani 1 1 d . . . O1 O 0.2587(4) 1.33594(11) 0.0901(2) 0.0312(6) Uani 1 1 d . . . O2 O 0.2375(3) 0.95828(10) 0.47874(17) 0.0192(5) Uani 1 1 d . . . Cl1 Cl 0.26986(13) 0.78855(4) 0.16124(7) 0.0297(2) Uani 1 1 d . . . Ag1 Ag 0.27063(3) 0.868622(11) 0.030018(19) 0.01874(9) 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 0.0157(15) 0.0168(15) 0.0162(16) -0.0028(13) -0.0018(12) -0.0004(12) C2 0.0168(15) 0.0215(16) 0.0141(15) 0.0013(13) 0.0031(12) 0.0020(12) C3 0.0184(16) 0.0181(15) 0.0143(15) 0.0031(13) -0.0001(12) -0.0030(12) C4 0.0273(18) 0.0208(17) 0.0186(17) -0.0086(14) 0.0029(14) 0.0022(13) C5 0.0091(14) 0.0178(15) 0.0139(15) -0.0007(12) 0.0000(12) -0.0014(11) C6 0.0165(15) 0.0132(14) 0.0156(15) -0.0033(12) 0.0004(12) -0.0013(11) C7 0.0112(14) 0.0143(14) 0.0143(15) -0.0003(12) 0.0004(12) 0.0015(11) C8 0.035(2) 0.0158(16) 0.0212(18) 0.0061(14) 0.0040(15) -0.0016(14) C9 0.034(2) 0.0203(18) 0.037(2) 0.0028(16) 0.0094(17) -0.0048(15) C10 0.037(2) 0.0181(17) 0.029(2) -0.0026(15) 0.0016(16) 0.0005(14) C11 0.0331(19) 0.0145(15) 0.0229(18) -0.0008(13) 0.0077(15) 0.0020(13) C12 0.0215(16) 0.0181(15) 0.0140(16) 0.0008(12) 0.0043(13) 0.0028(12) C13 0.0226(17) 0.0189(16) 0.0158(16) -0.0020(13) 0.0023(13) 0.0004(13) C14 0.0236(17) 0.0167(16) 0.0174(17) 0.0007(13) 0.0055(13) 0.0012(12) C15 0.0284(17) 0.0114(14) 0.0155(16) 0.0020(12) 0.0016(13) 0.0003(12) N1 0.0175(13) 0.0170(13) 0.0130(13) -0.0025(10) 0.0015(10) -0.0002(10) N2 0.0137(13) 0.0152(13) 0.0129(13) 0.0016(10) 0.0015(10) 0.0006(10) N3 0.0201(14) 0.0146(13) 0.0131(13) 0.0004(10) 0.0008(10) -0.0005(10) N4 0.0194(13) 0.0125(12) 0.0139(13) 0.0014(10) 0.0022(10) 0.0004(10) N5 0.0190(13) 0.0130(12) 0.0108(12) -0.0016(10) 0.0018(10) 0.0004(10) N6 0.0308(16) 0.0106(13) 0.0199(15) -0.0005(11) 0.0051(12) -0.0014(11) N7 0.0236(14) 0.0130(12) 0.0112(13) -0.0002(10) 0.0045(11) 0.0009(10) O1 0.0441(16) 0.0127(12) 0.0376(16) 0.0006(11) 0.0080(12) -0.0011(10) O2 0.0266(12) 0.0192(11) 0.0122(11) 0.0025(9) 0.0037(9) 0.0034(9) Cl1 0.0370(5) 0.0217(4) 0.0306(5) 0.0110(4) 0.0047(4) 0.0010(3) Ag1 0.02407(14) 0.01457(13) 0.01770(14) 0.00242(9) 0.00240(10) -0.00026(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.347(4) . ? C1 N2 1.377(4) . ? C1 Ag1 2.074(3) . ? C2 C3 1.342(4) . ? C2 N1 1.388(4) . ? C2 H2 0.9500 . ? C3 N2 1.396(4) . ? C3 H3 0.9500 . ? C4 N1 1.468(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.323(4) . ? C5 N5 1.322(4) . ? C5 N2 1.427(4) . ? C6 N6 1.344(4) . ? C6 N4 1.346(4) . ? C6 N3 1.358(4) . ? C7 N4 1.339(4) . ? C7 N7 1.351(4) . ? C7 N5 1.364(4) . ? C8 N6 1.470(4) . ? C8 C9 1.516(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.430(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O1 1.436(4) . ? C10 C11 1.509(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N6 1.468(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N7 1.461(4) . ? C12 C13 1.503(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O2 1.437(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O2 1.438(4) . ? C14 C15 1.518(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N7 1.467(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? Cl1 Ag1 2.3321(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 103.6(3) . . ? N1 C1 Ag1 128.4(2) . . ? N2 C1 Ag1 127.7(2) . . ? C3 C2 N1 107.6(3) . . ? C3 C2 H2 126.2 . . ? N1 C2 H2 126.2 . . ? C2 C3 N2 105.8(3) . . ? C2 C3 H3 127.1 . . ? N2 C3 H3 127.1 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N5 129.7(3) . . ? N3 C5 N2 113.9(3) . . ? N5 C5 N2 116.3(3) . . ? N6 C6 N4 117.5(3) . . ? N6 C6 N3 117.6(3) . . ? N4 C6 N3 124.9(3) . . ? N4 C7 N7 117.0(3) . . ? N4 C7 N5 125.2(3) . . ? N7 C7 N5 117.8(3) . . ? N6 C8 C9 108.0(3) . . ? N6 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N6 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? O1 C9 C8 112.2(3) . . ? O1 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? O1 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O1 C10 C11 111.2(3) . . ? O1 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? O1 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N6 C11 C10 110.0(3) . . ? N6 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N6 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N7 C12 C13 109.5(2) . . ? N7 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? N7 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? O2 C13 C12 112.3(3) . . ? O2 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? O2 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? O2 C14 C15 111.9(2) . . ? O2 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? O2 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N7 C15 C14 110.2(3) . . ? N7 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N7 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C1 N1 C2 111.6(2) . . ? C1 N1 C4 124.7(3) . . ? C2 N1 C4 123.7(3) . . ? C1 N2 C3 111.4(3) . . ? C1 N2 C5 125.4(2) . . ? C3 N2 C5 123.2(2) . . ? C5 N3 C6 112.7(2) . . ? C7 N4 C6 115.2(2) . . ? C5 N5 C7 112.2(2) . . ? C6 N6 C11 122.2(3) . . ? C6 N6 C8 123.3(3) . . ? C11 N6 C8 113.8(2) . . ? C7 N7 C12 122.3(2) . . ? C7 N7 C15 124.1(2) . . ? C12 N7 C15 113.2(2) . . ? C9 O1 C10 109.3(2) . . ? C13 O2 C14 111.0(2) . . ? C1 Ag1 Cl1 175.38(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.5(3) . . . . ? N6 C8 C9 O1 -56.9(4) . . . . ? O1 C10 C11 N6 55.4(4) . . . . ? N7 C12 C13 O2 -55.8(3) . . . . ? O2 C14 C15 N7 53.6(3) . . . . ? N2 C1 N1 C2 0.3(3) . . . . ? Ag1 C1 N1 C2 -173.8(2) . . . . ? N2 C1 N1 C4 -179.1(3) . . . . ? Ag1 C1 N1 C4 6.7(4) . . . . ? C3 C2 N1 C1 0.1(3) . . . . ? C3 C2 N1 C4 179.6(3) . . . . ? N1 C1 N2 C3 -0.6(3) . . . . ? Ag1 C1 N2 C3 173.6(2) . . . . ? N1 C1 N2 C5 176.8(3) . . . . ? Ag1 C1 N2 C5 -9.0(4) . . . . ? C2 C3 N2 C1 0.7(3) . . . . ? C2 C3 N2 C5 -176.8(3) . . . . ? N3 C5 N2 C1 -176.8(3) . . . . ? N5 C5 N2 C1 3.4(4) . . . . ? N3 C5 N2 C3 0.3(4) . . . . ? N5 C5 N2 C3 -179.6(3) . . . . ? N5 C5 N3 C6 -1.2(4) . . . . ? N2 C5 N3 C6 179.0(2) . . . . ? N6 C6 N3 C5 -178.8(3) . . . . ? N4 C6 N3 C5 2.2(4) . . . . ? N7 C7 N4 C6 176.5(3) . . . . ? N5 C7 N4 C6 -1.8(4) . . . . ? N6 C6 N4 C7 -179.8(3) . . . . ? N3 C6 N4 C7 -0.9(4) . . . . ? N3 C5 N5 C7 -1.1(4) . . . . ? N2 C5 N5 C7 178.7(2) . . . . ? N4 C7 N5 C5 2.6(4) . . . . ? N7 C7 N5 C5 -175.7(3) . . . . ? N4 C6 N6 C11 -15.3(5) . . . . ? N3 C6 N6 C11 165.7(3) . . . . ? N4 C6 N6 C8 175.0(3) . . . . ? N3 C6 N6 C8 -4.0(5) . . . . ? C10 C11 N6 C6 136.7(3) . . . . ? C10 C11 N6 C8 -52.7(4) . . . . ? C9 C8 N6 C6 -137.0(3) . . . . ? C9 C8 N6 C11 52.5(4) . . . . ? N4 C7 N7 C12 1.8(4) . . . . ? N5 C7 N7 C12 -179.8(3) . . . . ? N4 C7 N7 C15 174.0(3) . . . . ? N5 C7 N7 C15 -7.6(4) . . . . ? C13 C12 N7 C7 -133.2(3) . . . . ? C13 C12 N7 C15 53.8(3) . . . . ? C14 C15 N7 C7 134.2(3) . . . . ? C14 C15 N7 C12 -53.0(3) . . . . ? C8 C9 O1 C10 61.7(4) . . . . ? C11 C10 O1 C9 -60.2(4) . . . . ? C12 C13 O2 C14 57.9(3) . . . . ? C15 C14 O2 C13 -56.4(3) . . . . ? N1 C1 Ag1 Cl1 37.7(13) . . . . ? N2 C1 Ag1 Cl1 -135.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.483 _refine_diff_density_min -0.810 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 915432' ####################################################################### # # 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_2011ncs0503a #TrackingRef 'web_deposit_cif_file_3_GrahamJ.Tizzard_1355313337.2011ncs0503a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H25 Au Cl N7' _chemical_formula_sum 'C17 H25 Au Cl N7' _chemical_formula_weight 559.86 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.142(6) _cell_length_b 12.612(2) _cell_length_c 9.2699(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.990(7) _cell_angle_gamma 90.00 _cell_volume 3759.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13222 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.8 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.978 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 7.985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6049 _exptl_absorpt_correction_T_max 0.9244 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32275 _diffrn_reflns_av_R_equivalents 0.2412 _diffrn_reflns_av_sigmaI/netI 0.1369 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3305 _reflns_number_gt 2130 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0797P)^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 3305 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1668 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7153(4) 0.4732(11) 1.0690(15) 0.033(3) Uani 1 1 d . . . C2 C 0.7202(5) 0.6505(10) 1.0823(17) 0.043(4) Uani 1 1 d . . . H2 H 0.7147 0.7233 1.0596 0.052 Uiso 1 1 calc R . . C3 C 0.7479(5) 0.6144(10) 1.1941(17) 0.042(4) Uani 1 1 d . . . H3 H 0.7667 0.6550 1.2669 0.050 Uiso 1 1 calc R . . C4 C 0.7698(4) 0.4317(11) 1.2939(15) 0.040(4) Uani 1 1 d . . . H4A H 0.7585 0.3598 1.2765 0.060 Uiso 1 1 calc R . . H4B H 0.7695 0.4543 1.3947 0.060 Uiso 1 1 calc R . . H4C H 0.7985 0.4323 1.2828 0.060 Uiso 1 1 calc R . . C5 C 0.6673(5) 0.5787(11) 0.8720(17) 0.043(4) Uani 1 1 d . . . C6 C 0.6233(4) 0.6875(10) 0.7301(17) 0.038(4) Uani 1 1 d . . . C7 C 0.6210(4) 0.5123(10) 0.6806(15) 0.036(3) Uani 1 1 d . . . C8 C 0.6286(4) 0.8807(9) 0.7741(16) 0.039(4) Uani 1 1 d . . . H8A H 0.6394 0.9258 0.7042 0.046 Uiso 1 1 calc R . . H8B H 0.6524 0.8587 0.8556 0.046 Uiso 1 1 calc R . . C9 C 0.5972(5) 0.9430(10) 0.8373(18) 0.047(4) Uani 1 1 d . . . H9A H 0.5882 0.8994 0.9127 0.056 Uiso 1 1 calc R . . H9B H 0.6105 1.0080 0.8867 0.056 Uiso 1 1 calc R . . C10 C 0.5599(5) 0.9726(11) 0.716(2) 0.057(5) Uani 1 1 d . . . H10A H 0.5683 1.0234 0.6471 0.068 Uiso 1 1 calc R . . H10B H 0.5390 1.0076 0.7600 0.068 Uiso 1 1 calc R . . C11 C 0.5410(5) 0.8738(11) 0.631(2) 0.055(4) Uani 1 1 d . . . H11A H 0.5294 0.8281 0.6974 0.065 Uiso 1 1 calc R . . H11B H 0.5178 0.8956 0.5469 0.065 Uiso 1 1 calc R . . C12 C 0.5718(5) 0.8106(10) 0.5706(15) 0.036(3) Uani 1 1 d . . . H12A H 0.5588 0.7438 0.5256 0.044 Uiso 1 1 calc R . . H12B H 0.5809 0.8516 0.4931 0.044 Uiso 1 1 calc R . . C13 C 0.5651(5) 0.4358(10) 0.4871(15) 0.038(4) Uani 1 1 d . . . H13A H 0.5668 0.3966 0.3962 0.046 Uiso 1 1 calc R . . H13B H 0.5585 0.5108 0.4597 0.046 Uiso 1 1 calc R . . C14 C 0.5315(5) 0.3884(10) 0.5521(17) 0.044(4) Uani 1 1 d . . . H14A H 0.5277 0.4334 0.6352 0.053 Uiso 1 1 calc R . . H14B H 0.5050 0.3874 0.4751 0.053 Uiso 1 1 calc R . . C15 C 0.5422(5) 0.2775(10) 0.6079(15) 0.041(4) Uani 1 1 d . . . H15A H 0.5423 0.2300 0.5229 0.050 Uiso 1 1 calc R . . H15B H 0.5209 0.2514 0.6579 0.050 Uiso 1 1 calc R . . C16 C 0.5844(5) 0.2755(10) 0.7156(16) 0.042(4) Uani 1 1 d . . . H16A H 0.5836 0.3183 0.8044 0.051 Uiso 1 1 calc R . . H16B H 0.5916 0.2018 0.7483 0.051 Uiso 1 1 calc R . . C17 C 0.6167(5) 0.3192(9) 0.6435(17) 0.040(4) Uani 1 1 d . . . H17A H 0.6443 0.3184 0.7146 0.049 Uiso 1 1 calc R . . H17B H 0.6183 0.2756 0.5562 0.049 Uiso 1 1 calc R . . Au1 Au 0.696898(18) 0.32753(4) 1.01489(6) 0.0380(2) Uani 1 1 d . . . Cl1 Cl 0.67516(12) 0.1574(2) 0.9622(4) 0.0414(9) Uani 1 1 d . . . N1 N 0.7448(4) 0.5036(8) 1.1871(12) 0.038(3) Uani 1 1 d . . . N2 N 0.6999(4) 0.5664(8) 1.0011(11) 0.033(3) Uani 1 1 d . . . N3 N 0.6554(4) 0.6789(8) 0.8442(13) 0.039(3) Uani 1 1 d . . . N4 N 0.6040(4) 0.6083(8) 0.6448(13) 0.037(3) Uani 1 1 d . . . N5 N 0.6527(4) 0.4928(8) 0.7989(12) 0.036(3) Uani 1 1 d . . . N6 N 0.6079(4) 0.7869(8) 0.6963(13) 0.040(3) Uani 1 1 d . . . N7 N 0.6047(4) 0.4294(8) 0.5966(12) 0.035(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 C1 0.027(7) 0.039(8) 0.040(8) 0.009(7) 0.023(7) 0.004(6) C2 0.064(11) 0.019(7) 0.048(9) -0.010(6) 0.014(9) -0.005(7) C3 0.043(9) 0.023(7) 0.058(10) -0.008(7) 0.011(8) -0.009(7) C4 0.033(8) 0.044(8) 0.038(8) -0.001(7) 0.000(7) -0.001(7) C5 0.042(9) 0.035(8) 0.053(10) 0.002(7) 0.010(8) 0.008(7) C6 0.036(9) 0.029(8) 0.050(9) -0.004(7) 0.014(7) 0.000(6) C7 0.040(8) 0.023(7) 0.043(8) -0.001(6) 0.008(7) 0.000(6) C8 0.042(9) 0.019(7) 0.051(9) -0.013(6) 0.004(7) -0.003(6) C9 0.057(11) 0.023(7) 0.059(10) -0.007(7) 0.012(9) -0.012(7) C10 0.048(10) 0.032(8) 0.092(13) -0.021(9) 0.017(10) -0.005(7) C11 0.049(10) 0.032(8) 0.081(12) -0.009(8) 0.013(9) -0.006(7) C12 0.038(8) 0.032(7) 0.036(8) -0.001(6) 0.003(7) 0.002(6) C13 0.047(9) 0.025(7) 0.042(9) 0.003(6) 0.008(7) 0.000(6) C14 0.040(9) 0.037(8) 0.057(10) 0.007(7) 0.012(8) 0.001(7) C15 0.061(11) 0.031(7) 0.037(8) 0.009(6) 0.022(8) 0.000(7) C16 0.055(10) 0.024(7) 0.049(9) 0.002(7) 0.016(8) -0.001(7) C17 0.048(9) 0.017(6) 0.053(9) 0.008(6) 0.006(8) 0.003(6) Au1 0.0397(4) 0.0259(3) 0.0459(4) 0.0002(3) 0.0054(3) -0.0010(3) Cl1 0.046(2) 0.0225(17) 0.052(2) -0.0018(15) 0.0057(18) -0.0019(15) N1 0.040(7) 0.036(6) 0.035(6) 0.008(5) 0.006(6) 0.003(6) N2 0.039(7) 0.028(6) 0.033(6) 0.001(5) 0.007(6) -0.004(5) N3 0.047(8) 0.028(6) 0.042(7) -0.004(5) 0.011(6) -0.001(6) N4 0.038(7) 0.024(6) 0.048(7) 0.000(5) 0.005(6) -0.003(5) N5 0.043(7) 0.019(5) 0.044(7) -0.004(5) 0.006(6) -0.006(5) N6 0.044(8) 0.017(5) 0.053(8) -0.003(5) 0.000(6) 0.001(5) N7 0.042(7) 0.018(5) 0.043(7) -0.004(5) 0.007(6) -0.003(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.335(17) . ? C1 N2 1.373(16) . ? C1 Au1 1.962(14) . ? C2 C3 1.29(2) . ? C2 N2 1.378(16) . ? C2 H2 0.9500 . ? C3 N1 1.402(16) . ? C3 H3 0.9500 . ? C4 N1 1.447(16) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N5 1.306(17) . ? C5 N3 1.330(16) . ? C5 N2 1.415(17) . ? C6 N3 1.312(18) . ? C6 N4 1.336(16) . ? C6 N6 1.361(16) . ? C7 N7 1.337(15) . ? C7 N4 1.344(16) . ? C7 N5 1.345(16) . ? C8 N6 1.466(15) . ? C8 C9 1.53(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.50(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.527(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.50(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N6 1.486(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N7 1.454(17) . ? C13 C14 1.511(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.503(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.51(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.50(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N7 1.482(14) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? Au1 Cl1 2.278(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 104.3(11) . . ? N1 C1 Au1 126.8(10) . . ? N2 C1 Au1 128.8(10) . . ? C3 C2 N2 109.1(12) . . ? C3 C2 H2 125.5 . . ? N2 C2 H2 125.5 . . ? C2 C3 N1 106.5(12) . . ? C2 C3 H3 126.8 . . ? N1 C3 H3 126.8 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N5 C5 N3 129.3(14) . . ? N5 C5 N2 117.3(12) . . ? N3 C5 N2 113.4(13) . . ? N3 C6 N4 126.5(12) . . ? N3 C6 N6 116.6(12) . . ? N4 C6 N6 117.0(12) . . ? N7 C7 N4 118.3(12) . . ? N7 C7 N5 117.3(11) . . ? N4 C7 N5 124.4(12) . . ? N6 C8 C9 108.8(11) . . ? N6 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? N6 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C10 C9 C8 110.8(13) . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 110.1(12) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 113.3(13) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? N6 C12 C11 107.8(12) . . ? N6 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? N6 C12 H12B 110.1 . . ? C11 C12 H12B 110.1 . . ? H12A C12 H12B 108.5 . . ? N7 C13 C14 109.1(11) . . ? N7 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? N7 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C13 111.8(12) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C14 C15 C16 110.3(12) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 110.3(12) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N7 C17 C16 107.7(12) . . ? N7 C17 H17A 110.2 . . ? C16 C17 H17A 110.2 . . ? N7 C17 H17B 110.2 . . ? C16 C17 H17B 110.2 . . ? H17A C17 H17B 108.5 . . ? C1 Au1 Cl1 177.5(4) . . ? C1 N1 C3 110.8(11) . . ? C1 N1 C4 124.5(11) . . ? C3 N1 C4 124.7(11) . . ? C1 N2 C2 109.3(11) . . ? C1 N2 C5 127.2(11) . . ? C2 N2 C5 123.4(11) . . ? C6 N3 C5 112.3(12) . . ? C6 N4 C7 114.5(12) . . ? C5 N5 C7 112.9(11) . . ? C6 N6 C8 121.7(11) . . ? C6 N6 C12 123.4(11) . . ? C8 N6 C12 114.6(10) . . ? C7 N7 C13 122.3(11) . . ? C7 N7 C17 121.3(11) . . ? C13 N7 C17 113.0(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 N2 C2 C3 N1 -1.4(18) . . . . ? N6 C8 C9 C10 -56.9(15) . . . . ? C8 C9 C10 C11 54.7(18) . . . . ? C9 C10 C11 C12 -55(2) . . . . ? C10 C11 C12 N6 53.8(17) . . . . ? N7 C13 C14 C15 -54.5(15) . . . . ? C13 C14 C15 C16 54.0(16) . . . . ? C14 C15 C16 C17 -56.8(16) . . . . ? C15 C16 C17 N7 59.3(15) . . . . ? N1 C1 Au1 Cl1 51(10) . . . . ? N2 C1 Au1 Cl1 -125(9) . . . . ? N2 C1 N1 C3 0.3(15) . . . . ? Au1 C1 N1 C3 -176.7(10) . . . . ? N2 C1 N1 C4 179.7(12) . . . . ? Au1 C1 N1 C4 3(2) . . . . ? C2 C3 N1 C1 0.7(18) . . . . ? C2 C3 N1 C4 -178.7(14) . . . . ? N1 C1 N2 C2 -1.1(15) . . . . ? Au1 C1 N2 C2 175.8(11) . . . . ? N1 C1 N2 C5 -178.5(13) . . . . ? Au1 C1 N2 C5 -2(2) . . . . ? C3 C2 N2 C1 1.6(18) . . . . ? C3 C2 N2 C5 179.2(14) . . . . ? N5 C5 N2 C1 -8(2) . . . . ? N3 C5 N2 C1 171.2(13) . . . . ? N5 C5 N2 C2 175.0(14) . . . . ? N3 C5 N2 C2 -6(2) . . . . ? N4 C6 N3 C5 -2(2) . . . . ? N6 C6 N3 C5 177.7(13) . . . . ? N5 C5 N3 C6 3(2) . . . . ? N2 C5 N3 C6 -175.6(13) . . . . ? N3 C6 N4 C7 -2(2) . . . . ? N6 C6 N4 C7 178.4(13) . . . . ? N7 C7 N4 C6 -177.2(13) . . . . ? N5 C7 N4 C6 5(2) . . . . ? N3 C5 N5 C7 -1(2) . . . . ? N2 C5 N5 C7 178.2(13) . . . . ? N7 C7 N5 C5 178.5(13) . . . . ? N4 C7 N5 C5 -4(2) . . . . ? N3 C6 N6 C8 6(2) . . . . ? N4 C6 N6 C8 -174.8(13) . . . . ? N3 C6 N6 C12 179.9(13) . . . . ? N4 C6 N6 C12 -1(2) . . . . ? C9 C8 N6 C6 -125.4(14) . . . . ? C9 C8 N6 C12 59.9(16) . . . . ? C11 C12 N6 C6 127.6(14) . . . . ? C11 C12 N6 C8 -57.9(16) . . . . ? N4 C7 N7 C13 -12(2) . . . . ? N5 C7 N7 C13 166.1(13) . . . . ? N4 C7 N7 C17 -169.2(13) . . . . ? N5 C7 N7 C17 9(2) . . . . ? C14 C13 N7 C7 -99.9(15) . . . . ? C14 C13 N7 C17 59.4(15) . . . . ? C16 C17 N7 C7 97.2(15) . . . . ? C16 C17 N7 C13 -62.2(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.155 _refine_diff_density_min -2.991 _refine_diff_density_rms 0.275 _database_code_depnum_ccdc_archive 'CCDC 915433' ####################################################################### # # 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_2011ncs0190ba #TrackingRef 'web_deposit_cif_file_4_GrahamJ.Tizzard_1355313337.2011ncs0190ba.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H21 Au Cl N7 O2' _chemical_formula_sum 'C15 H21 Au Cl N7 O2' _chemical_formula_weight 563.80 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.0612(5) _cell_length_b 20.5399(16) _cell_length_c 12.4713(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.603(7) _cell_angle_gamma 90.00 _cell_volume 1800.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13846 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 8.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2861 _exptl_absorpt_correction_T_max 0.8508 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_source_power 2.0 _diffrn_source_voltage 50.0 _diffrn_source_current 40.0 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Mitegen _diffrn_detector RX _diffrn_measurement_device ; Crystal Goniometer ; _diffrn_measurement_device_type ; Rigaku RAXIS conversion ; _diffrn_detector_area_resol_mean 10.0000 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19537 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.46 _reflns_number_total 4105 _reflns_number_gt 3612 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. reflection -1 0 14 omitted from final refinement calculations ; _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^)+(0.0291P)^2^+2.1352P] 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 4105 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2862(5) 0.9331(2) -0.0898(3) 0.0163(8) Uani 1 1 d . . . C2 C 0.3473(5) 0.9797(2) -0.2467(3) 0.0190(9) Uani 1 1 d . . . H2 H 0.3738 0.9837 -0.3197 0.023 Uiso 1 1 calc R . . C3 C 0.3266(5) 1.0287(2) -0.1781(3) 0.0191(9) Uani 1 1 d . . . H3 H 0.3369 1.0739 -0.1922 0.023 Uiso 1 1 calc R . . C4 C 0.3330(6) 0.8575(2) -0.2417(4) 0.0239(10) Uani 1 1 d . . . H4A H 0.2789 0.8249 -0.1962 0.036 Uiso 1 1 calc R . . H4B H 0.4661 0.8466 -0.2494 0.036 Uiso 1 1 calc R . . H4C H 0.2607 0.8579 -0.3129 0.036 Uiso 1 1 calc R . . C5 C 0.2442(4) 1.0371(2) 0.0106(3) 0.0132(8) Uani 1 1 d . . . C6 C 0.2086(5) 1.1346(2) 0.0840(3) 0.0164(8) Uani 1 1 d . . . C7 C 0.1748(5) 1.0430(2) 0.1809(3) 0.0159(8) Uani 1 1 d . . . C8 C 0.2532(6) 1.2356(2) -0.0189(3) 0.0230(10) Uani 1 1 d . . . H8A H 0.1343 1.2492 -0.0617 0.028 Uiso 1 1 calc R . . H8B H 0.3253 1.2071 -0.0644 0.028 Uiso 1 1 calc R . . C9 C 0.3704(6) 1.2945(2) 0.0157(4) 0.0303(10) Uani 1 1 d . . . H9A H 0.4938 1.2802 0.0528 0.036 Uiso 1 1 calc R . . H9B H 0.3968 1.3197 -0.0488 0.036 Uiso 1 1 calc R . . C10 C 0.2430(7) 1.2997(2) 0.1822(4) 0.0301(10) Uani 1 1 d . . . H10A H 0.1801 1.3284 0.2317 0.036 Uiso 1 1 calc R . . H10B H 0.3667 1.2859 0.2193 0.036 Uiso 1 1 calc R . . C11 C 0.1214(6) 1.2410(2) 0.1565(3) 0.0243(9) Uani 1 1 d . . . H11A H 0.1095 1.2157 0.2231 0.029 Uiso 1 1 calc R . . H11B H -0.0076 1.2547 0.1268 0.029 Uiso 1 1 calc R . . C12 C 0.1164(5) 1.0502(2) 0.3719(3) 0.0178(8) Uani 1 1 d . . . H12A H -0.0154 1.0438 0.3906 0.021 Uiso 1 1 calc R . . H12B H 0.1357 1.0972 0.3591 0.021 Uiso 1 1 calc R . . C13 C 0.2562(5) 1.0269(2) 0.4633(3) 0.0204(9) Uani 1 1 d . . . H13A H 0.3869 1.0382 0.4474 0.025 Uiso 1 1 calc R . . H13B H 0.2308 1.0498 0.5303 0.025 Uiso 1 1 calc R . . C14 C 0.2766(5) 0.9229(2) 0.3837(3) 0.0200(9) Uani 1 1 d . . . H14A H 0.2625 0.8757 0.3967 0.024 Uiso 1 1 calc R . . H14B H 0.4083 0.9308 0.3659 0.024 Uiso 1 1 calc R . . C15 C 0.1382(6) 0.9433(2) 0.2897(3) 0.0208(9) Uani 1 1 d . . . H15A H 0.1706 0.9212 0.2234 0.025 Uiso 1 1 calc R . . H15B H 0.0076 0.9302 0.3031 0.025 Uiso 1 1 calc R . . Au1 Au 0.262932(19) 0.866372(8) 0.022990(12) 0.01710(6) Uani 1 1 d . . . Cl1 Cl 0.24978(16) 0.78864(6) 0.15374(9) 0.0303(3) Uani 1 1 d . . . N1 N 0.3230(4) 0.92183(17) -0.1919(2) 0.0159(7) Uani 1 1 d . . . N2 N 0.2867(4) 0.99973(17) -0.0810(2) 0.0138(7) Uani 1 1 d . . . N3 N 0.2490(4) 1.10040(19) -0.0050(3) 0.0160(7) Uani 1 1 d . . . N4 N 0.1730(4) 1.10801(18) 0.1784(3) 0.0170(7) Uani 1 1 d . . . N5 N 0.2082(4) 1.00340(18) 0.0963(2) 0.0165(7) Uani 1 1 d . . . N6 N 0.2080(5) 1.20009(18) 0.0772(3) 0.0200(7) Uani 1 1 d . . . N7 N 0.1458(5) 1.01336(18) 0.2751(2) 0.0178(7) Uani 1 1 d . . . O1 O 0.2754(4) 1.33556(17) 0.0866(3) 0.0335(8) Uani 1 1 d . . . O2 O 0.2447(4) 0.95827(16) 0.4800(2) 0.0210(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 C1 0.0102(16) 0.018(2) 0.0202(19) -0.0030(17) -0.0004(14) 0.0029(15) C2 0.0180(18) 0.024(3) 0.0153(18) -0.0008(18) 0.0032(15) -0.0008(16) C3 0.0182(18) 0.022(2) 0.0168(19) 0.0054(18) 0.0016(15) -0.0003(16) C4 0.028(2) 0.018(3) 0.025(2) -0.0052(19) -0.0005(17) 0.0025(17) C5 0.0107(16) 0.013(2) 0.0151(18) -0.0006(16) -0.0006(13) -0.0002(14) C6 0.0142(17) 0.018(2) 0.0166(19) 0.0002(16) 0.0003(14) 0.0011(15) C7 0.0144(16) 0.016(2) 0.0170(18) 0.0009(17) -0.0015(14) -0.0017(15) C8 0.034(2) 0.014(2) 0.021(2) 0.0026(18) 0.0052(17) -0.0007(17) C9 0.035(2) 0.019(3) 0.038(3) 0.000(2) 0.010(2) -0.003(2) C10 0.038(2) 0.019(3) 0.032(2) 0.000(2) -0.001(2) 0.005(2) C11 0.034(2) 0.014(2) 0.025(2) -0.0052(19) 0.0044(18) -0.0010(18) C12 0.0238(19) 0.015(2) 0.0146(18) 0.0000(16) 0.0025(15) 0.0003(16) C13 0.0226(19) 0.021(3) 0.0175(19) -0.0001(18) 0.0015(15) 0.0019(17) C14 0.0226(19) 0.016(2) 0.021(2) -0.0011(17) 0.0016(16) 0.0011(16) C15 0.031(2) 0.013(2) 0.0180(19) -0.0014(17) 0.0006(16) 0.0005(17) Au1 0.01908(9) 0.01328(11) 0.01881(10) 0.00094(6) 0.00122(6) 0.00012(6) Cl1 0.0369(6) 0.0202(6) 0.0339(6) 0.0113(5) 0.0034(5) -0.0004(5) N1 0.0174(15) 0.019(2) 0.0111(15) -0.0042(14) -0.0001(12) 0.0013(13) N2 0.0153(14) 0.0128(19) 0.0134(15) 0.0008(13) 0.0023(11) 0.0017(13) N3 0.0178(15) 0.0129(19) 0.0175(15) -0.0007(15) 0.0031(12) -0.0026(13) N4 0.0179(15) 0.016(2) 0.0172(16) 0.0031(15) 0.0007(12) -0.0024(14) N5 0.0186(15) 0.016(2) 0.0144(15) -0.0006(14) 0.0011(12) 0.0002(13) N6 0.0293(17) 0.011(2) 0.0208(17) -0.0012(15) 0.0064(14) -0.0007(14) N7 0.0289(17) 0.014(2) 0.0106(15) 0.0010(14) 0.0024(13) -0.0005(14) O1 0.0405(18) 0.0148(19) 0.046(2) -0.0024(16) 0.0053(15) -0.0027(14) O2 0.0292(15) 0.0197(19) 0.0140(14) 0.0013(12) 0.0017(11) 0.0028(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(5) . ? C1 N2 1.372(5) . ? C1 Au1 1.983(4) . ? C2 C3 1.338(6) . ? C2 N1 1.390(5) . ? C2 H2 0.9500 . ? C3 N2 1.402(5) . ? C3 H3 0.9500 . ? C4 N1 1.465(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.316(6) . ? C5 N5 1.318(5) . ? C5 N2 1.432(5) . ? C6 N4 1.343(5) . ? C6 N6 1.349(5) . ? C6 N3 1.367(5) . ? C7 N4 1.335(5) . ? C7 N7 1.356(5) . ? C7 N5 1.371(5) . ? C8 N6 1.464(5) . ? C8 C9 1.505(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.435(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O1 1.437(6) . ? C10 C11 1.497(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N6 1.475(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N7 1.457(5) . ? C12 C13 1.511(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O2 1.429(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O2 1.440(5) . ? C14 C15 1.511(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N7 1.452(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? Au1 Cl1 2.2905(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 104.4(3) . . ? N1 C1 Au1 126.1(3) . . ? N2 C1 Au1 129.2(3) . . ? C3 C2 N1 107.5(3) . . ? C3 C2 H2 126.2 . . ? N1 C2 H2 126.2 . . ? C2 C3 N2 106.1(4) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N5 130.4(4) . . ? N3 C5 N2 113.6(3) . . ? N5 C5 N2 115.9(4) . . ? N4 C6 N6 117.4(4) . . ? N4 C6 N3 125.1(4) . . ? N6 C6 N3 117.4(4) . . ? N4 C7 N7 117.9(4) . . ? N4 C7 N5 125.3(4) . . ? N7 C7 N5 116.8(4) . . ? N6 C8 C9 108.9(4) . . ? N6 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? N6 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O1 C9 C8 111.8(4) . . ? O1 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? O1 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O1 C10 C11 111.7(4) . . ? O1 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? O1 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? N6 C11 C10 109.6(4) . . ? N6 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N6 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N7 C12 C13 109.0(3) . . ? N7 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? N7 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? O2 C13 C12 112.4(3) . . ? O2 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? O2 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? O2 C14 C15 111.4(3) . . ? O2 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? O2 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N7 C15 C14 110.1(3) . . ? N7 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N7 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? C1 Au1 Cl1 177.56(10) . . ? C1 N1 C2 111.3(3) . . ? C1 N1 C4 125.4(4) . . ? C2 N1 C4 123.3(3) . . ? C1 N2 C3 110.6(3) . . ? C1 N2 C5 126.8(3) . . ? C3 N2 C5 122.5(4) . . ? C5 N3 C6 112.1(3) . . ? C7 N4 C6 115.1(4) . . ? C5 N5 C7 111.9(4) . . ? C6 N6 C8 123.3(4) . . ? C6 N6 C11 121.7(4) . . ? C8 N6 C11 113.8(4) . . ? C7 N7 C15 124.4(3) . . ? C7 N7 C12 122.0(4) . . ? C15 N7 C12 113.6(3) . . ? C9 O1 C10 109.4(4) . . ? C13 O2 C14 111.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.8(4) . . . . ? N6 C8 C9 O1 -56.5(5) . . . . ? O1 C10 C11 N6 55.3(5) . . . . ? N7 C12 C13 O2 -55.1(4) . . . . ? O2 C14 C15 N7 54.3(4) . . . . ? N1 C1 Au1 Cl1 73(3) . . . . ? N2 C1 Au1 Cl1 -101(3) . . . . ? N2 C1 N1 C2 0.3(4) . . . . ? Au1 C1 N1 C2 -174.4(2) . . . . ? N2 C1 N1 C4 -178.5(3) . . . . ? Au1 C1 N1 C4 6.8(5) . . . . ? C3 C2 N1 C1 0.3(4) . . . . ? C3 C2 N1 C4 179.2(3) . . . . ? N1 C1 N2 C3 -0.8(4) . . . . ? Au1 C1 N2 C3 173.7(3) . . . . ? N1 C1 N2 C5 176.3(3) . . . . ? Au1 C1 N2 C5 -9.2(5) . . . . ? C2 C3 N2 C1 1.1(4) . . . . ? C2 C3 N2 C5 -176.2(3) . . . . ? N3 C5 N2 C1 -177.7(3) . . . . ? N5 C5 N2 C1 2.8(5) . . . . ? N3 C5 N2 C3 -0.9(5) . . . . ? N5 C5 N2 C3 179.6(3) . . . . ? N5 C5 N3 C6 -0.3(5) . . . . ? N2 C5 N3 C6 -179.8(3) . . . . ? N4 C6 N3 C5 1.8(5) . . . . ? N6 C6 N3 C5 -179.5(3) . . . . ? N7 C7 N4 C6 177.9(3) . . . . ? N5 C7 N4 C6 -0.4(5) . . . . ? N6 C6 N4 C7 179.8(3) . . . . ? N3 C6 N4 C7 -1.5(5) . . . . ? N3 C5 N5 C7 -1.3(5) . . . . ? N2 C5 N5 C7 178.2(3) . . . . ? N4 C7 N5 C5 1.6(5) . . . . ? N7 C7 N5 C5 -176.7(3) . . . . ? N4 C6 N6 C8 177.0(3) . . . . ? N3 C6 N6 C8 -1.8(5) . . . . ? N4 C6 N6 C11 -16.6(5) . . . . ? N3 C6 N6 C11 164.6(3) . . . . ? C9 C8 N6 C6 -140.3(4) . . . . ? C9 C8 N6 C11 52.4(5) . . . . ? C10 C11 N6 C6 140.2(4) . . . . ? C10 C11 N6 C8 -52.2(5) . . . . ? N4 C7 N7 C15 178.2(3) . . . . ? N5 C7 N7 C15 -3.4(5) . . . . ? N4 C7 N7 C12 -0.9(5) . . . . ? N5 C7 N7 C12 177.5(3) . . . . ? C14 C15 N7 C7 126.6(4) . . . . ? C14 C15 N7 C12 -54.2(4) . . . . ? C13 C12 N7 C7 -126.8(4) . . . . ? C13 C12 N7 C15 54.0(4) . . . . ? C8 C9 O1 C10 61.0(5) . . . . ? C11 C10 O1 C9 -60.2(5) . . . . ? C12 C13 O2 C14 57.6(4) . . . . ? C15 C14 O2 C13 -56.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.261 _refine_diff_density_min -1.174 _refine_diff_density_rms 0.155 _database_code_depnum_ccdc_archive 'CCDC 915434' ####################################################################### # # 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_2011ncs0604r1a #TrackingRef 'web_deposit_cif_file_5_GrahamJ.Tizzard_1355313337.2011ncs0604r1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '0.75(C16 H23 Au1 Cl N7 O), 0.25(C16 H23 Ag1 Cl N7 O)' _chemical_formula_sum 'C16 H23 Ag0.25 Au0.75 Cl N7 O' _chemical_formula_weight 539.56 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.0421(7) _cell_length_b 20.089(2) _cell_length_c 13.0920(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.120(7) _cell_angle_gamma 90.00 _cell_volume 1847.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13976 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Platelet _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.940 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 6.412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8309 _exptl_absorpt_correction_T_max 0.9387 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19357 _diffrn_reflns_av_R_equivalents 0.1547 _diffrn_reflns_av_sigmaI/netI 0.1157 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3267 _reflns_number_gt 2206 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Occupancies of Au and Ag initially allowed to freely refine. Were found to be approximately 3:1 and so occupancies were then fixed. ; _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^)+(0.0626P)^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 3267 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0972 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 0.7046(15) 0.0651(6) 1.0943(9) 0.040(3) Uani 1 1 d . . . C2 C 0.6469(17) 0.0100(6) 1.2391(10) 0.045(3) Uani 1 1 d . . . H2 H 0.6195 0.0022 1.3080 0.054 Uiso 1 1 calc R A . C3 C 0.6751(17) -0.0359(7) 1.1685(9) 0.046(3) Uani 1 1 d . A . H3 H 0.6686 -0.0827 1.1777 0.055 Uiso 1 1 calc R . . C4 C 0.6478(19) 0.1341(6) 1.2448(10) 0.048(3) Uani 1 1 d . . . H4A H 0.7517 0.1386 1.2984 0.073 Uiso 1 1 calc R A . H4B H 0.5254 0.1359 1.2760 0.073 Uiso 1 1 calc R . . H4C H 0.6547 0.1706 1.1955 0.073 Uiso 1 1 calc R . . C5 C 0.7600(16) -0.0357(6) 0.9880(9) 0.041(3) Uani 1 1 d . . . C6 C 0.7989(17) -0.1319(6) 0.9076(10) 0.043(3) Uani 1 1 d . . . C7 C 0.8213(16) -0.0334(6) 0.8237(10) 0.039(3) Uani 1 1 d . . . C8 C 0.7803(19) -0.2386(7) 0.9959(11) 0.054(4) Uani 1 1 d . . . H8A H 0.7102 -0.2121 1.0448 0.065 Uiso 1 1 calc R A . H8B H 0.9054 -0.2510 1.0299 0.065 Uiso 1 1 calc R . . C9 C 0.669(2) -0.3006(6) 0.9656(11) 0.056(4) Uani 1 1 d . A . H9A H 0.6584 -0.3290 1.0268 0.067 Uiso 1 1 calc R . . H9B H 0.5386 -0.2879 0.9393 0.067 Uiso 1 1 calc R . . C10 C 0.771(2) -0.2972(7) 0.7980(11) 0.061(4) Uani 1 1 d . A . H10A H 0.6408 -0.2844 0.7716 0.073 Uiso 1 1 calc R . . H10B H 0.8295 -0.3229 0.7439 0.073 Uiso 1 1 calc R . . C11 C 0.884(2) -0.2364(6) 0.8208(10) 0.059(4) Uani 1 1 d . . . H11A H 1.0179 -0.2488 0.8402 0.070 Uiso 1 1 calc R A . H11B H 0.8826 -0.2082 0.7587 0.070 Uiso 1 1 calc R . . C12 C 0.884(2) -0.0324(7) 0.6405(9) 0.053(3) Uani 1 1 d . . . H12A H 0.8643 -0.0810 0.6468 0.064 Uiso 1 1 calc R A . H12B H 1.0182 -0.0246 0.6259 0.064 Uiso 1 1 calc R . . C13 C 0.7513(18) -0.0047(8) 0.5534(11) 0.057(4) Uani 1 1 d . A . H13A H 0.7860 -0.0240 0.4878 0.068 Uiso 1 1 calc R . . H13B H 0.6189 -0.0181 0.5639 0.068 Uiso 1 1 calc R . . C14 C 0.7616(19) 0.0698(7) 0.5474(10) 0.055(4) Uani 1 1 d . . . H14A H 0.6658 0.0859 0.4940 0.066 Uiso 1 1 calc R A . H14B H 0.8890 0.0830 0.5270 0.066 Uiso 1 1 calc R . . C15 C 0.7260(19) 0.1026(7) 0.6492(11) 0.060(4) Uani 1 1 d . A . H15A H 0.7482 0.1511 0.6446 0.072 Uiso 1 1 calc R . . H15B H 0.5919 0.0955 0.6647 0.072 Uiso 1 1 calc R . . C16 C 0.856(2) 0.0738(6) 0.7332(10) 0.053(3) Uani 1 1 d . . . H16A H 0.9883 0.0870 0.7228 0.063 Uiso 1 1 calc R A . H16B H 0.8220 0.0923 0.7996 0.063 Uiso 1 1 calc R . . Au1 Au 0.7133(4) 0.13850(19) 0.9955(3) 0.0322(4) Uani 0.75 1 d P A 1 Ag1 Ag 0.744(3) 0.1383(12) 0.9904(18) 0.0322(4) Uani 0.25 1 d P A 2 Cl1 Cl 0.7155(4) 0.22657(13) 0.8803(2) 0.0357(7) Uani 1 1 d . . . N1 N 0.6650(13) 0.0711(5) 1.1927(7) 0.041(2) Uani 1 1 d . A . N2 N 0.7159(13) -0.0033(5) 1.0789(8) 0.039(2) Uani 1 1 d . A . N3 N 0.7632(12) -0.1015(5) 0.9951(8) 0.042(3) Uani 1 1 d . A . N4 N 0.8323(13) -0.1001(5) 0.8188(7) 0.041(2) Uani 1 1 d . A . N5 N 0.7864(14) 0.0024(5) 0.9084(8) 0.042(2) Uani 1 1 d . A . N6 N 0.8078(15) -0.1989(5) 0.9039(8) 0.050(3) Uani 1 1 d . A . N7 N 0.8433(15) 0.0010(5) 0.7367(8) 0.048(3) Uani 1 1 d . A . O1 O 0.7595(14) -0.3386(5) 0.8871(8) 0.064(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 C1 0.028(6) 0.046(8) 0.047(8) -0.006(6) 0.008(6) -0.005(5) C2 0.053(8) 0.047(8) 0.036(7) 0.001(6) 0.009(6) -0.006(6) C3 0.049(8) 0.053(9) 0.039(7) 0.017(7) 0.023(6) 0.002(6) C4 0.057(9) 0.046(8) 0.042(7) -0.007(7) 0.003(6) 0.002(6) C5 0.041(8) 0.038(7) 0.045(8) -0.006(6) -0.003(6) 0.004(5) C6 0.046(8) 0.030(7) 0.055(8) -0.005(6) 0.011(6) -0.007(6) C7 0.032(7) 0.036(7) 0.048(8) 0.007(6) 0.005(6) 0.003(5) C8 0.056(9) 0.049(8) 0.058(9) -0.001(7) 0.010(7) -0.004(6) C9 0.074(10) 0.047(8) 0.051(9) 0.011(7) 0.019(7) -0.004(7) C10 0.091(11) 0.041(9) 0.051(9) 0.001(7) 0.007(8) 0.017(7) C11 0.092(11) 0.044(9) 0.040(8) -0.006(7) 0.001(8) 0.010(7) C12 0.065(9) 0.059(9) 0.036(7) 0.000(7) 0.008(7) -0.001(7) C13 0.044(8) 0.074(11) 0.052(9) -0.004(8) 0.008(7) 0.006(7) C14 0.061(9) 0.061(10) 0.041(8) -0.001(7) -0.003(7) -0.004(7) C15 0.053(9) 0.055(9) 0.071(10) 0.010(8) 0.001(8) -0.005(7) C16 0.068(9) 0.050(9) 0.041(7) -0.003(6) 0.015(7) 0.006(7) Au1 0.0331(11) 0.0294(3) 0.0346(5) 0.0009(3) 0.0060(7) 0.0002(7) Ag1 0.0331(11) 0.0294(3) 0.0346(5) 0.0009(3) 0.0060(7) 0.0002(7) Cl1 0.0433(17) 0.0250(15) 0.0386(16) 0.0117(12) 0.0014(13) -0.0022(12) N1 0.048(6) 0.041(6) 0.036(6) -0.008(5) 0.011(5) 0.010(5) N2 0.043(6) 0.034(6) 0.040(6) 0.004(5) 0.008(5) 0.008(4) N3 0.039(6) 0.040(6) 0.047(6) -0.011(5) 0.010(5) 0.000(4) N4 0.047(6) 0.040(6) 0.038(6) 0.009(5) 0.012(5) 0.000(5) N5 0.050(7) 0.037(6) 0.042(6) 0.008(5) 0.012(5) 0.004(5) N6 0.057(7) 0.046(7) 0.049(7) -0.009(5) 0.011(5) 0.000(5) N7 0.055(7) 0.045(7) 0.043(6) -0.003(5) 0.007(5) 0.000(5) O1 0.079(7) 0.053(6) 0.060(6) -0.010(5) 0.006(5) -0.001(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.343(14) . ? C1 N2 1.393(15) . ? C1 Au1 1.965(13) . ? C1 Ag1 2.04(3) . ? C2 C3 1.330(17) . ? C2 N1 1.379(15) . ? C2 H2 0.9500 . ? C3 N2 1.391(14) . ? C3 H3 0.9500 . ? C4 N1 1.448(14) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N5 1.317(15) . ? C5 N3 1.325(16) . ? C5 N2 1.410(15) . ? C6 N3 1.337(14) . ? C6 N6 1.348(14) . ? C6 N4 1.361(15) . ? C7 N4 1.344(14) . ? C7 N7 1.351(15) . ? C7 N5 1.358(15) . ? C8 N6 1.470(16) . ? C8 C9 1.510(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.463(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O1 1.439(15) . ? C10 C11 1.477(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N6 1.458(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N7 1.473(15) . ? C12 C13 1.526(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.501(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.524(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.494(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N7 1.466(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? Au1 Cl1 2.325(5) . ? Ag1 Cl1 2.29(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 N1 C1 N2 104.2(10) . . ? N1 C1 Au1 125.7(9) . . ? N2 C1 Au1 129.9(9) . . ? N1 C1 Ag1 128.6(11) . . ? N2 C1 Ag1 127.2(10) . . ? Au1 C1 Ag1 6.3(6) . . ? C3 C2 N1 106.7(11) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? C2 C3 N2 108.1(11) . . ? C2 C3 H3 126.0 . . ? N2 C3 H3 126.0 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N5 C5 N3 129.1(11) . . ? N5 C5 N2 117.0(11) . . ? N3 C5 N2 113.9(11) . . ? N3 C6 N6 119.9(11) . . ? N3 C6 N4 124.9(11) . . ? N6 C6 N4 115.2(11) . . ? N4 C7 N7 117.4(11) . . ? N4 C7 N5 125.5(11) . . ? N7 C7 N5 117.1(11) . . ? N6 C8 C9 109.2(11) . . ? N6 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? N6 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O1 C9 C8 111.7(11) . . ? O1 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? O1 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? O1 C10 C11 112.1(11) . . ? O1 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? O1 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N6 C11 C10 110.8(12) . . ? N6 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? N6 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N7 C12 C13 109.0(11) . . ? N7 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? N7 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C14 C13 C12 111.9(12) . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 111.9(12) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 110.2(12) . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N7 C16 C15 112.0(11) . . ? N7 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? N7 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C1 Au1 Cl1 178.3(4) . . ? C1 Ag1 Cl1 166.5(10) . . ? Ag1 Cl1 Au1 5.6(5) . . ? C1 N1 C2 112.0(10) . . ? C1 N1 C4 124.1(11) . . ? C2 N1 C4 123.9(10) . . ? C3 N2 C1 109.0(10) . . ? C3 N2 C5 124.5(11) . . ? C1 N2 C5 126.5(10) . . ? C5 N3 C6 113.5(11) . . ? C7 N4 C6 114.4(11) . . ? C5 N5 C7 112.6(10) . . ? C6 N6 C11 124.4(11) . . ? C6 N6 C8 120.2(11) . . ? C11 N6 C8 114.1(10) . . ? C7 N7 C16 123.2(10) . . ? C7 N7 C12 121.9(11) . . ? C16 N7 C12 114.3(10) . . ? C10 O1 C9 108.7(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 N1 C2 C3 N2 1.5(14) . . . . ? N6 C8 C9 O1 54.8(15) . . . . ? O1 C10 C11 N6 -56.0(15) . . . . ? N7 C12 C13 C14 53.8(15) . . . . ? C12 C13 C14 C15 -54.1(15) . . . . ? C13 C14 C15 C16 52.9(15) . . . . ? C14 C15 C16 N7 -53.3(15) . . . . ? N1 C1 Au1 Cl1 -44(15) . . . . ? N2 C1 Au1 Cl1 128(14) . . . . ? Ag1 C1 Au1 Cl1 -165(19) . . . . ? N1 C1 Ag1 Cl1 -62(6) . . . . ? N2 C1 Ag1 Cl1 119(5) . . . . ? Au1 C1 Ag1 Cl1 2(2) . . . . ? C1 Ag1 Cl1 Au1 -2(2) . . . . ? C1 Au1 Cl1 Ag1 165(19) . . . . ? N2 C1 N1 C2 -1.3(13) . . . . ? Au1 C1 N1 C2 172.6(8) . . . . ? Ag1 C1 N1 C2 179.5(11) . . . . ? N2 C1 N1 C4 177.3(10) . . . . ? Au1 C1 N1 C4 -8.7(16) . . . . ? Ag1 C1 N1 C4 -1.8(18) . . . . ? C3 C2 N1 C1 -0.1(14) . . . . ? C3 C2 N1 C4 -178.8(11) . . . . ? C2 C3 N2 C1 -2.4(13) . . . . ? C2 C3 N2 C5 177.9(10) . . . . ? N1 C1 N2 C3 2.2(12) . . . . ? Au1 C1 N2 C3 -171.3(9) . . . . ? Ag1 C1 N2 C3 -178.6(11) . . . . ? N1 C1 N2 C5 -178.1(10) . . . . ? Au1 C1 N2 C5 8.3(16) . . . . ? Ag1 C1 N2 C5 1.1(17) . . . . ? N5 C5 N2 C3 176.9(11) . . . . ? N3 C5 N2 C3 -1.2(16) . . . . ? N5 C5 N2 C1 -2.7(16) . . . . ? N3 C5 N2 C1 179.2(9) . . . . ? N5 C5 N3 C6 0.1(18) . . . . ? N2 C5 N3 C6 177.9(10) . . . . ? N6 C6 N3 C5 179.5(10) . . . . ? N4 C6 N3 C5 1.0(17) . . . . ? N7 C7 N4 C6 -176.7(10) . . . . ? N5 C7 N4 C6 2.0(17) . . . . ? N3 C6 N4 C7 -1.9(17) . . . . ? N6 C6 N4 C7 179.5(10) . . . . ? N3 C5 N5 C7 0.0(17) . . . . ? N2 C5 N5 C7 -177.8(10) . . . . ? N4 C7 N5 C5 -1.2(17) . . . . ? N7 C7 N5 C5 177.6(10) . . . . ? N3 C6 N6 C11 -166.5(11) . . . . ? N4 C6 N6 C11 12.2(17) . . . . ? N3 C6 N6 C8 -0.6(18) . . . . ? N4 C6 N6 C8 178.1(11) . . . . ? C10 C11 N6 C6 -141.7(12) . . . . ? C10 C11 N6 C8 51.6(15) . . . . ? C9 C8 N6 C6 142.0(12) . . . . ? C9 C8 N6 C11 -50.8(15) . . . . ? N4 C7 N7 C16 -173.1(10) . . . . ? N5 C7 N7 C16 8.1(17) . . . . ? N4 C7 N7 C12 -1.9(17) . . . . ? N5 C7 N7 C12 179.2(11) . . . . ? C15 C16 N7 C7 -131.3(12) . . . . ? C15 C16 N7 C12 56.9(15) . . . . ? C13 C12 N7 C7 132.6(12) . . . . ? C13 C12 N7 C16 -55.6(14) . . . . ? C11 C10 O1 C9 60.2(15) . . . . ? C8 C9 O1 C10 -59.9(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.958 _refine_diff_density_min -1.287 _refine_diff_density_rms 0.191 # start Validation Reply Form _vrf_PLAT973_ALERT_2_B ; PROBLEM: Large Calcd. Positive Residual Density on Au1 1.71 eA-3. RESPONSE: Not possible to face index crystal due to size, thus standard absorption correction used resulting in residual density above ; _database_code_depnum_ccdc_archive 'CCDC 915435' ####################################################################### # # 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_2011ncs0439a #TrackingRef 'web_deposit_cif_file_6_GrahamJ.Tizzard_1355313337.2011ncs0439a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N4 O2' _chemical_formula_sum 'C10 H16 N4 O2' _chemical_formula_weight 224.27 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' O O 0.0106 0.0060 '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' _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 7.3461(6) _cell_length_b 8.7159(8) _cell_length_c 8.8803(9) _cell_angle_alpha 91.820(7) _cell_angle_beta 102.865(7) _cell_angle_gamma 100.602(7) _cell_volume 543.28(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4277 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9892 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5038 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2470 _reflns_number_gt 1996 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0930P)^2^+0.7104P] 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 2470 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2163 _refine_ls_wR_factor_gt 0.2089 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.8314(3) 0.6777(3) -0.0012(3) 0.0175(5) Uani 1 1 d . . . C2 C 0.7539(3) 0.4293(3) 0.0581(3) 0.0153(5) Uani 1 1 d . . . C3 C 0.6292(3) 0.5046(3) -0.1760(3) 0.0172(5) Uani 1 1 d . . . C4 C 0.9148(4) 0.3444(3) 0.3062(3) 0.0206(5) Uani 1 1 d . . . H4A H 0.9700 0.4576 0.3269 0.025 Uiso 1 1 calc R . . H4B H 1.0186 0.2889 0.2981 0.025 Uiso 1 1 calc R . . C5 C 0.8290(4) 0.2863(3) 0.4398(3) 0.0206(5) Uani 1 1 d . . . H5A H 0.7345 0.3493 0.4551 0.025 Uiso 1 1 calc R . . H5B H 0.9305 0.2995 0.5363 0.025 Uiso 1 1 calc R . . C6 C 0.7325(4) 0.1138(3) 0.4065(3) 0.0197(5) Uani 1 1 d . . . H6A H 0.8286 0.0493 0.3996 0.024 Uiso 1 1 calc R . . H6B H 0.6716 0.0786 0.4916 0.024 Uiso 1 1 calc R . . C7 C 0.5824(4) 0.0934(3) 0.2537(3) 0.0220(5) Uani 1 1 d . . . H7A H 0.5249 -0.0191 0.2291 0.026 Uiso 1 1 calc R . . H7B H 0.4801 0.1495 0.2651 0.026 Uiso 1 1 calc R . . C8 C 0.6666(4) 0.1557(3) 0.1203(3) 0.0216(5) Uani 1 1 d . . . H8A H 0.7544 0.0892 0.0975 0.026 Uiso 1 1 calc R . . H8B H 0.5632 0.1510 0.0263 0.026 Uiso 1 1 calc R . . C9 C 1.0549(4) 0.8666(3) 0.1798(3) 0.0210(5) Uani 1 1 d . . . H9A H 0.9845 0.8523 0.2616 0.031 Uiso 1 1 calc R . . H9B H 1.1202 0.9761 0.1857 0.031 Uiso 1 1 calc R . . H9C H 1.1491 0.7987 0.1935 0.031 Uiso 1 1 calc R . . C10 C 0.4157(4) 0.3214(3) -0.3691(3) 0.0225(5) Uani 1 1 d . . . H10A H 0.5040 0.2489 -0.3624 0.034 Uiso 1 1 calc R . . H10B H 0.3423 0.3178 -0.4762 0.034 Uiso 1 1 calc R . . H10C H 0.3286 0.2909 -0.3013 0.034 Uiso 1 1 calc R . . O1 O 0.9248(3) 0.8266(2) 0.0313(2) 0.0217(4) Uani 1 1 d . . . O2 O 0.5211(3) 0.4772(2) -0.3213(2) 0.0221(4) Uani 1 1 d . . . N1 N 0.7209(3) 0.6531(2) -0.1446(2) 0.0197(5) Uani 1 1 d . . . N2 N 0.6351(3) 0.3877(2) -0.0839(2) 0.0169(4) Uani 1 1 d . . . N3 N 0.8576(3) 0.5755(2) 0.1049(2) 0.0170(5) Uani 1 1 d . . . N4 N 0.7705(3) 0.3181(2) 0.1595(2) 0.0184(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 C1 0.0210(11) 0.0144(11) 0.0186(12) 0.0048(9) 0.0074(9) 0.0029(9) C2 0.0181(11) 0.0147(11) 0.0135(11) 0.0022(8) 0.0046(9) 0.0030(8) C3 0.0206(11) 0.0186(12) 0.0132(11) 0.0034(8) 0.0047(9) 0.0047(9) C4 0.0241(12) 0.0169(11) 0.0162(11) 0.0045(9) -0.0002(10) -0.0019(9) C5 0.0280(12) 0.0165(11) 0.0140(11) 0.0027(8) 0.0009(9) 0.0009(9) C6 0.0271(12) 0.0149(11) 0.0154(11) 0.0050(8) 0.0033(9) 0.0013(9) C7 0.0252(12) 0.0156(11) 0.0212(12) 0.0035(9) 0.0014(10) -0.0021(9) C8 0.0322(13) 0.0126(11) 0.0148(11) 0.0016(8) -0.0004(10) -0.0019(10) C9 0.0243(12) 0.0146(11) 0.0200(12) 0.0028(9) 0.0009(10) -0.0015(9) C10 0.0270(13) 0.0222(13) 0.0151(11) 0.0022(9) 0.0013(10) 0.0008(10) O1 0.0289(9) 0.0141(9) 0.0182(9) 0.0053(6) 0.0009(7) -0.0010(7) O2 0.0296(10) 0.0191(9) 0.0149(9) 0.0044(6) 0.0010(7) 0.0027(7) N1 0.0251(11) 0.0177(10) 0.0161(10) 0.0058(8) 0.0040(8) 0.0040(8) N2 0.0217(10) 0.0156(10) 0.0124(9) 0.0033(7) 0.0025(8) 0.0026(8) N3 0.0218(10) 0.0140(10) 0.0148(9) 0.0034(7) 0.0039(8) 0.0021(8) N4 0.0252(10) 0.0122(9) 0.0136(10) 0.0032(7) 0.0000(8) -0.0022(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N3 1.325(3) . ? C1 N1 1.336(3) . ? C1 O1 1.340(3) . ? C2 N4 1.347(3) . ? C2 N3 1.359(3) . ? C2 N2 1.360(3) . ? C3 N2 1.328(3) . ? C3 N1 1.334(3) . ? C3 O2 1.344(3) . ? C4 N4 1.466(3) . ? C4 C5 1.521(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.528(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.525(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N4 1.470(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.436(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O2 1.433(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C1 N1 128.2(2) . . ? N3 C1 O1 119.4(2) . . ? N1 C1 O1 112.3(2) . . ? N4 C2 N3 117.6(2) . . ? N4 C2 N2 117.9(2) . . ? N3 C2 N2 124.5(2) . . ? N2 C3 N1 128.2(2) . . ? N2 C3 O2 119.2(2) . . ? N1 C3 O2 112.6(2) . . ? N4 C4 C5 111.1(2) . . ? N4 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N4 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 110.47(19) . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 109.21(19) . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C8 C7 C6 112.0(2) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N4 C8 C7 110.7(2) . . ? N4 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 O1 C9 117.73(18) . . ? C3 O2 C10 117.83(19) . . ? C3 N1 C1 111.9(2) . . ? C3 N2 C2 113.5(2) . . ? C1 N3 C2 113.6(2) . . ? C2 N4 C4 122.11(19) . . ? C2 N4 C8 122.1(2) . . ? C4 N4 C8 115.09(19) . . ? 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 N4 C4 C5 C6 55.8(3) . . . . ? C4 C5 C6 C7 -56.7(3) . . . . ? C5 C6 C7 C8 55.8(3) . . . . ? C6 C7 C8 N4 -53.1(3) . . . . ? N3 C1 O1 C9 2.1(3) . . . . ? N1 C1 O1 C9 -177.37(19) . . . . ? N2 C3 O2 C10 0.4(3) . . . . ? N1 C3 O2 C10 179.88(19) . . . . ? N2 C3 N1 C1 1.0(4) . . . . ? O2 C3 N1 C1 -178.43(18) . . . . ? N3 C1 N1 C3 0.4(4) . . . . ? O1 C1 N1 C3 179.72(19) . . . . ? N1 C3 N2 C2 -1.3(4) . . . . ? O2 C3 N2 C2 178.07(19) . . . . ? N4 C2 N2 C3 -179.6(2) . . . . ? N3 C2 N2 C3 0.4(3) . . . . ? N1 C1 N3 C2 -1.1(4) . . . . ? O1 C1 N3 C2 179.57(19) . . . . ? N4 C2 N3 C1 -179.4(2) . . . . ? N2 C2 N3 C1 0.7(3) . . . . ? N3 C2 N4 C4 -9.2(3) . . . . ? N2 C2 N4 C4 170.8(2) . . . . ? N3 C2 N4 C8 -179.3(2) . . . . ? N2 C2 N4 C8 0.7(3) . . . . ? C5 C4 N4 C2 134.5(2) . . . . ? C5 C4 N4 C8 -54.8(3) . . . . ? C7 C8 N4 C2 -136.4(2) . . . . ? C7 C8 N4 C4 52.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.679 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 915436' ####################################################################### # # 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_2012ncs0227r1a #TrackingRef 'web_deposit_cif_file_7_GrahamJ.Tizzard_1355313337.2012ncs0227r1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H21 Ag Cl N7, C H Cl3' _chemical_formula_sum 'C15 H22 Ag Cl4 N7' _chemical_formula_weight 550.07 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 6.6913(3) _cell_length_b 32.6023(17) _cell_length_c 9.7316(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.225(7) _cell_angle_gamma 90.00 _cell_volume 2117.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10813 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9300 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14274 _diffrn_reflns_av_R_equivalents 0.0802 _diffrn_reflns_av_sigmaI/netI 0.0992 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4842 _reflns_number_gt 3182 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Minor twin component indicated by CheckCIF cannot be resolved ; _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^)+(0.0596P)^2^+12.8379P] 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 4842 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.1801 _refine_ls_wR_factor_gt 0.1601 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.2783(10) 0.0433(2) 0.4614(7) 0.0192(14) Uani 1 1 d . . . C2 C 0.2736(11) 0.0416(3) 0.2268(8) 0.0291(18) Uani 1 1 d . . . H2 H 0.2779 0.0506 0.1343 0.035 Uiso 1 1 calc R . . C3 C 0.2502(11) 0.0029(2) 0.2704(8) 0.0268(17) Uani 1 1 d . . . H3 H 0.2343 -0.0208 0.2140 0.032 Uiso 1 1 calc R . . C4 C 0.3144(12) 0.1099(2) 0.3435(9) 0.0319(19) Uani 1 1 d . . . H4A H 0.3247 0.1203 0.4383 0.048 Uiso 1 1 calc R . . H4B H 0.1984 0.1225 0.2923 0.048 Uiso 1 1 calc R . . H4C H 0.4365 0.1169 0.2989 0.048 Uiso 1 1 calc R . . C5 C 0.2285(10) -0.0316(2) 0.4944(7) 0.0201(15) Uani 1 1 d . . . C6 C 0.1712(11) -0.0989(2) 0.5023(8) 0.0248(16) Uani 1 1 d . . . C7 C 0.2132(10) -0.0619(2) 0.6985(8) 0.0231(15) Uani 1 1 d . . . C8 C 0.1435(14) -0.1393(2) 0.2892(8) 0.036(2) Uani 1 1 d . . . H8A H 0.1662 -0.1121 0.2477 0.043 Uiso 1 1 calc R . . H8B H 0.0146 -0.1502 0.2478 0.043 Uiso 1 1 calc R . . C9 C 0.3100(16) -0.1678(3) 0.2586(10) 0.047(2) Uani 1 1 d . . . H9A H 0.4401 -0.1550 0.2890 0.057 Uiso 1 1 calc R . . H9B H 0.3075 -0.1723 0.1579 0.057 Uiso 1 1 calc R . . C10 C 0.2907(19) -0.2088(3) 0.3314(12) 0.063(3) Uani 1 1 d . . . H10A H 0.4086 -0.2261 0.3161 0.076 Uiso 1 1 calc R . . H10B H 0.1694 -0.2233 0.2923 0.076 Uiso 1 1 calc R . . C11 C 0.2762(14) -0.2024(3) 0.4869(10) 0.042(2) Uani 1 1 d . . . H11A H 0.2515 -0.2291 0.5314 0.050 Uiso 1 1 calc R . . H11B H 0.4043 -0.1912 0.5284 0.050 Uiso 1 1 calc R . . C12 C 0.1096(14) -0.1734(2) 0.5107(9) 0.038(2) Uani 1 1 d . . . H12A H -0.0198 -0.1861 0.4781 0.046 Uiso 1 1 calc R . . H12B H 0.1069 -0.1681 0.6106 0.046 Uiso 1 1 calc R . . C13 C 0.1890(12) -0.0959(2) 0.9226(8) 0.0303(18) Uani 1 1 d . . . H13A H 0.0638 -0.0913 0.9667 0.045 Uiso 1 1 calc R . . H13B H 0.2994 -0.0993 0.9935 0.045 Uiso 1 1 calc R . . H13C H 0.1764 -0.1206 0.8654 0.045 Uiso 1 1 calc R . . C14 C 0.2622(13) -0.0221(2) 0.9116(8) 0.0310(18) Uani 1 1 d . . . H14A H 0.3228 -0.0020 0.8524 0.046 Uiso 1 1 calc R . . H14B H 0.3521 -0.0269 0.9942 0.046 Uiso 1 1 calc R . . H14C H 0.1337 -0.0116 0.9387 0.046 Uiso 1 1 calc R . . N1 N 0.2900(9) 0.06563(19) 0.3451(6) 0.0234(13) Uani 1 1 d . . . N2 N 0.2538(9) 0.00400(18) 0.4135(6) 0.0192(12) Uani 1 1 d . . . N3 N 0.2001(9) -0.06545(18) 0.4214(6) 0.0252(13) Uani 1 1 d . . . N4 N 0.1780(9) -0.09895(18) 0.6408(6) 0.0239(14) Uani 1 1 d . . . N5 N 0.2389(9) -0.02621(18) 0.6301(6) 0.0222(13) Uani 1 1 d . . . N6 N 0.1334(11) -0.13488(19) 0.4390(7) 0.0336(17) Uani 1 1 d . . . N7 N 0.2295(9) -0.06063(18) 0.8363(6) 0.0253(13) Uani 1 1 d . . . Cl1 Cl 0.3074(3) 0.09006(6) 0.88900(19) 0.0311(4) Uani 1 1 d . . . C51 C 0.7426(13) -0.3082(3) 0.4974(9) 0.039(2) Uani 1 1 d . . . H51 H 0.7521 -0.3352 0.5460 0.047 Uiso 1 1 calc R . . Cl51 Cl 0.5249(4) -0.30815(7) 0.3841(3) 0.0513(6) Uani 1 1 d . . . Cl52 Cl 0.9555(4) -0.30203(8) 0.4053(3) 0.0631(8) Uani 1 1 d . . . Cl53 Cl 0.7310(4) -0.26934(8) 0.6208(3) 0.0538(7) Uani 1 1 d . . . Ag1 Ag 0.28869(9) 0.062987(17) 0.66427(6) 0.02464(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.014(3) 0.024(3) 0.020(3) 0.001(3) 0.005(3) 0.005(3) C2 0.024(4) 0.041(5) 0.022(4) 0.004(3) 0.005(3) 0.009(4) C3 0.031(4) 0.028(4) 0.022(4) -0.003(3) 0.003(3) -0.002(3) C4 0.034(5) 0.024(4) 0.037(5) 0.010(3) 0.003(4) -0.004(3) C5 0.017(4) 0.022(3) 0.021(3) 0.007(3) 0.005(3) 0.006(3) C6 0.023(4) 0.026(4) 0.026(4) -0.001(3) 0.000(3) 0.002(3) C7 0.016(3) 0.025(4) 0.028(4) -0.007(3) 0.005(3) -0.002(3) C8 0.058(6) 0.026(4) 0.024(4) 0.001(3) -0.003(4) 0.006(4) C9 0.069(7) 0.028(4) 0.046(6) 0.007(4) 0.016(5) 0.008(5) C10 0.093(9) 0.029(5) 0.074(8) 0.005(5) 0.045(7) 0.016(5) C11 0.044(5) 0.030(4) 0.053(6) 0.014(4) 0.011(4) 0.004(4) C12 0.049(6) 0.032(4) 0.034(5) -0.004(4) 0.005(4) -0.004(4) C13 0.035(5) 0.035(4) 0.021(4) 0.006(3) 0.001(3) -0.003(4) C14 0.038(5) 0.031(4) 0.024(4) -0.004(3) -0.001(4) -0.001(4) N1 0.020(3) 0.025(3) 0.025(3) 0.004(3) 0.004(2) 0.003(3) N2 0.019(3) 0.024(3) 0.015(3) 0.000(2) 0.005(2) 0.003(2) N3 0.031(4) 0.022(3) 0.023(3) -0.002(3) 0.004(3) 0.004(3) N4 0.027(4) 0.024(3) 0.021(3) 0.000(3) 0.004(3) 0.002(3) N5 0.024(3) 0.024(3) 0.019(3) 0.001(2) 0.002(2) -0.001(3) N6 0.058(5) 0.022(3) 0.021(3) -0.001(3) 0.000(3) 0.003(3) N7 0.034(4) 0.024(3) 0.018(3) 0.002(3) 0.003(3) 0.002(3) Cl1 0.0433(12) 0.0279(9) 0.0221(9) -0.0037(8) 0.0030(8) 0.0026(9) C51 0.044(5) 0.028(4) 0.047(5) 0.009(4) 0.015(4) 0.003(4) Cl51 0.0618(16) 0.0425(13) 0.0495(14) 0.0035(11) 0.0029(12) 0.0146(12) Cl52 0.0635(17) 0.0407(13) 0.091(2) -0.0018(13) 0.0437(16) 0.0016(12) Cl53 0.0629(17) 0.0436(13) 0.0567(15) -0.0108(11) 0.0164(13) -0.0009(12) Ag1 0.0282(3) 0.0239(3) 0.0219(3) -0.0019(2) 0.0022(2) 0.0020(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.353(9) . ? C1 N2 1.369(9) . ? C1 Ag1 2.073(7) . ? C2 C3 1.343(11) . ? C2 N1 1.391(10) . ? C2 H2 0.9500 . ? C3 N2 1.392(9) . ? C3 H3 0.9500 . ? C4 N1 1.454(9) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.318(9) . ? C5 N5 1.329(9) . ? C5 N2 1.420(9) . ? C6 N6 1.341(9) . ? C6 N4 1.345(9) . ? C6 N3 1.367(9) . ? C7 N7 1.338(9) . ? C7 N4 1.345(9) . ? C7 N5 1.358(9) . ? C8 N6 1.471(10) . ? C8 C9 1.497(12) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.525(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.537(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.494(12) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N6 1.451(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N7 1.460(9) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N7 1.462(9) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? Cl1 Ag1 2.3532(19) . ? C51 Cl52 1.750(9) . ? C51 Cl53 1.751(9) . ? C51 Cl51 1.761(9) . ? C51 H51 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 103.4(6) . . ? N1 C1 Ag1 129.1(5) . . ? N2 C1 Ag1 127.5(5) . . ? C3 C2 N1 105.8(7) . . ? C3 C2 H2 127.1 . . ? N1 C2 H2 127.1 . . ? C2 C3 N2 107.3(7) . . ? C2 C3 H3 126.3 . . ? N2 C3 H3 126.3 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N5 129.9(6) . . ? N3 C5 N2 113.8(6) . . ? N5 C5 N2 116.3(6) . . ? N6 C6 N4 116.8(7) . . ? N6 C6 N3 117.6(7) . . ? N4 C6 N3 125.6(7) . . ? N7 C7 N4 116.4(7) . . ? N7 C7 N5 117.4(6) . . ? N4 C7 N5 126.1(7) . . ? N6 C8 C9 110.3(7) . . ? N6 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N6 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 111.2(8) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 110.6(8) . . ? 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 . . ? C12 C11 C10 109.9(8) . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N6 C12 C11 111.3(7) . . ? N6 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? N6 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? N7 C13 H13A 109.5 . . ? N7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 H14A 109.5 . . ? N7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 N1 C2 112.5(6) . . ? C1 N1 C4 123.9(6) . . ? C2 N1 C4 123.6(6) . . ? C1 N2 C3 110.9(6) . . ? C1 N2 C5 126.4(6) . . ? C3 N2 C5 122.7(6) . . ? C5 N3 C6 112.2(6) . . ? C7 N4 C6 114.1(6) . . ? C5 N5 C7 111.9(6) . . ? C6 N6 C12 124.1(7) . . ? C6 N6 C8 121.3(7) . . ? C12 N6 C8 114.0(6) . . ? C7 N7 C13 123.2(6) . . ? C7 N7 C14 121.8(6) . . ? C13 N7 C14 114.5(6) . . ? Cl52 C51 Cl53 110.3(5) . . ? Cl52 C51 Cl51 110.2(5) . . ? Cl53 C51 Cl51 110.6(5) . . ? Cl52 C51 H51 108.5 . . ? Cl53 C51 H51 108.5 . . ? Cl51 C51 H51 108.5 . . ? C1 Ag1 Cl1 175.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N2 -0.3(8) . . . . ? N6 C8 C9 C10 54.1(11) . . . . ? C8 C9 C10 C11 -54.3(13) . . . . ? C9 C10 C11 C12 54.2(12) . . . . ? C10 C11 C12 N6 -55.4(10) . . . . ? N2 C1 N1 C2 0.0(8) . . . . ? Ag1 C1 N1 C2 -178.9(5) . . . . ? N2 C1 N1 C4 179.3(6) . . . . ? Ag1 C1 N1 C4 0.4(10) . . . . ? C3 C2 N1 C1 0.2(9) . . . . ? C3 C2 N1 C4 -179.1(7) . . . . ? N1 C1 N2 C3 -0.2(8) . . . . ? Ag1 C1 N2 C3 178.7(5) . . . . ? N1 C1 N2 C5 -178.3(6) . . . . ? Ag1 C1 N2 C5 0.6(10) . . . . ? C2 C3 N2 C1 0.3(8) . . . . ? C2 C3 N2 C5 178.5(6) . . . . ? N3 C5 N2 C1 177.5(6) . . . . ? N5 C5 N2 C1 -3.3(10) . . . . ? N3 C5 N2 C3 -0.5(10) . . . . ? N5 C5 N2 C3 178.8(6) . . . . ? N5 C5 N3 C6 2.4(11) . . . . ? N2 C5 N3 C6 -178.4(6) . . . . ? N6 C6 N3 C5 177.6(7) . . . . ? N4 C6 N3 C5 -2.6(11) . . . . ? N7 C7 N4 C6 -177.4(6) . . . . ? N5 C7 N4 C6 0.7(11) . . . . ? N6 C6 N4 C7 -179.0(7) . . . . ? N3 C6 N4 C7 1.2(11) . . . . ? N3 C5 N5 C7 -0.8(11) . . . . ? N2 C5 N5 C7 -179.9(6) . . . . ? N7 C7 N5 C5 177.1(6) . . . . ? N4 C7 N5 C5 -1.0(10) . . . . ? N4 C6 N6 C12 -3.0(12) . . . . ? N3 C6 N6 C12 176.8(7) . . . . ? N4 C6 N6 C8 -173.5(7) . . . . ? N3 C6 N6 C8 6.3(11) . . . . ? C11 C12 N6 C6 -113.2(9) . . . . ? C11 C12 N6 C8 57.9(10) . . . . ? C9 C8 N6 C6 114.8(9) . . . . ? C9 C8 N6 C12 -56.6(10) . . . . ? N4 C7 N7 C13 -7.0(10) . . . . ? N5 C7 N7 C13 174.7(7) . . . . ? N4 C7 N7 C14 -178.3(7) . . . . ? N5 C7 N7 C14 3.4(10) . . . . ? N1 C1 Ag1 Cl1 -10(3) . . . . ? N2 C1 Ag1 Cl1 171(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.203 _refine_diff_density_min -0.905 _refine_diff_density_rms 0.178 _database_code_depnum_ccdc_archive 'CCDC 915437' ####################################################################### # # 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_2011ncs0411a #TrackingRef 'web_deposit_cif_file_8_GrahamJ.Tizzard_1355313337.2011ncs0411a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H21 Au Cl N7' _chemical_formula_sum 'C14 H21 Au Cl N7' _chemical_formula_weight 519.79 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.627(6) _cell_length_b 9.6686(8) _cell_length_c 26.780(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.24(4) _cell_angle_gamma 90.00 _cell_volume 1705.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6799 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Blade _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 8.791 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3522 _exptl_absorpt_correction_T_max 0.9172 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7571 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3756 _reflns_number_gt 3216 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0016P)^2^+7.6072P] 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 3756 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 0.2757(7) 0.5283(5) 0.04541(17) 0.0139(10) Uani 1 1 d . . . C2 C 0.2465(8) 0.7166(5) -0.0045(2) 0.0208(11) Uani 1 1 d . . . H2 H 0.2298 0.7733 -0.0337 0.025 Uiso 1 1 calc R . . C3 C 0.2737(8) 0.7592(6) 0.0436(2) 0.0228(11) Uani 1 1 d . . . H3 H 0.2799 0.8524 0.0549 0.027 Uiso 1 1 calc R . . C4 C 0.3223(8) 0.6496(7) 0.12829(18) 0.0279(13) Uani 1 1 d . . . H4A H 0.3248 0.5556 0.1420 0.042 Uiso 1 1 calc R . . H4B H 0.2114 0.7020 0.1407 0.042 Uiso 1 1 calc R . . H4C H 0.4518 0.6956 0.1388 0.042 Uiso 1 1 calc R . . C5 C 0.2220(7) 0.4921(5) -0.04778(17) 0.0161(9) Uani 1 1 d . . . C6 C 0.1665(7) 0.4869(6) -0.13121(17) 0.0182(10) Uani 1 1 d . . . C7 C 0.2051(7) 0.2867(5) -0.08679(18) 0.0161(10) Uani 1 1 d . . . C8 C 0.1360(10) 0.7037(6) -0.1796(2) 0.0309(14) Uani 1 1 d . . . H8A H 0.1469 0.7449 -0.1455 0.037 Uiso 1 1 calc R . . H8B H 0.0105 0.7393 -0.1987 0.037 Uiso 1 1 calc R . . C9 C 0.3187(10) 0.7455(6) -0.2057(2) 0.0335(14) Uani 1 1 d . . . H9A H 0.4446 0.7233 -0.1838 0.040 Uiso 1 1 calc R . . H9B H 0.3157 0.8467 -0.2115 0.040 Uiso 1 1 calc R . . C10 C 0.3206(10) 0.6703(7) -0.2561(2) 0.0360(14) Uani 1 1 d . . . H10A H 0.2080 0.7055 -0.2801 0.043 Uiso 1 1 calc R . . H10B H 0.4496 0.6905 -0.2702 0.043 Uiso 1 1 calc R . . C11 C 0.2984(10) 0.5157(7) -0.2505(2) 0.0346(14) Uani 1 1 d . . . H11A H 0.4219 0.4779 -0.2312 0.041 Uiso 1 1 calc R . . H11B H 0.2837 0.4719 -0.2841 0.041 Uiso 1 1 calc R . . C12 C 0.1145(9) 0.4817(6) -0.22363(19) 0.0319(13) Uani 1 1 d . . . H12A H -0.0106 0.5089 -0.2450 0.038 Uiso 1 1 calc R . . H12B H 0.1091 0.3808 -0.2177 0.038 Uiso 1 1 calc R . . C13 C 0.1935(9) 0.0665(6) -0.13159(19) 0.0233(11) Uani 1 1 d . . . H13A H 0.0598 0.0221 -0.1353 0.035 Uiso 1 1 calc R . . H13B H 0.2995 -0.0046 -0.1298 0.035 Uiso 1 1 calc R . . H13C H 0.2062 0.1268 -0.1605 0.035 Uiso 1 1 calc R . . C14 C 0.2389(9) 0.0700(6) -0.03919(19) 0.0255(12) Uani 1 1 d . . . H14A H 0.2588 0.1341 -0.0107 0.038 Uiso 1 1 calc R . . H14B H 0.3568 0.0087 -0.0388 0.038 Uiso 1 1 calc R . . H14C H 0.1166 0.0147 -0.0366 0.038 Uiso 1 1 calc R . . Au1 Au 0.28544(3) 0.33378(2) 0.071363(7) 0.01759(6) Uani 1 1 d . . . Cl1 Cl 0.2914(2) 0.11195(14) 0.10226(5) 0.0256(3) Uani 1 1 d . . . N1 N 0.2908(6) 0.6433(4) 0.07328(15) 0.0194(9) Uani 1 1 d . . . N2 N 0.2479(6) 0.5731(4) -0.00289(15) 0.0156(8) Uani 1 1 d . . . N3 N 0.1934(6) 0.5670(4) -0.08909(15) 0.0174(9) Uani 1 1 d . . . N4 N 0.1716(6) 0.3497(4) -0.13214(14) 0.0165(8) Uani 1 1 d . . . N5 N 0.2293(6) 0.3559(4) -0.04228(14) 0.0163(9) Uani 1 1 d . . . N6 N 0.1247(8) 0.5546(5) -0.17577(16) 0.0273(11) Uani 1 1 d . . . N7 N 0.2159(7) 0.1482(4) -0.08586(15) 0.0208(9) 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 0.011(2) 0.012(2) 0.019(2) -0.0028(19) 0.0036(16) -0.0011(19) C2 0.023(3) 0.014(2) 0.026(3) -0.003(2) 0.003(2) -0.001(2) C3 0.025(3) 0.014(3) 0.030(3) -0.011(2) 0.005(2) -0.005(2) C4 0.026(3) 0.039(4) 0.018(2) -0.012(3) 0.0022(19) -0.002(3) C5 0.013(2) 0.015(2) 0.020(2) -0.001(2) 0.0043(16) -0.001(2) C6 0.020(2) 0.018(3) 0.018(2) 0.002(2) 0.0054(18) 0.000(2) C7 0.013(2) 0.016(2) 0.020(2) -0.0006(19) 0.0023(18) -0.001(2) C8 0.059(4) 0.014(3) 0.021(3) 0.007(2) 0.009(3) 0.006(3) C9 0.055(4) 0.021(3) 0.023(3) 0.002(2) 0.000(3) -0.008(3) C10 0.043(3) 0.043(4) 0.022(3) 0.004(3) 0.006(2) -0.007(3) C11 0.052(4) 0.036(4) 0.016(2) -0.001(3) 0.002(2) 0.004(3) C12 0.050(4) 0.026(3) 0.018(3) -0.001(2) -0.004(2) -0.001(3) C13 0.032(3) 0.015(3) 0.022(3) -0.005(2) 0.002(2) 0.000(2) C14 0.041(3) 0.015(3) 0.020(3) 0.007(2) 0.002(2) 0.003(3) Au1 0.01812(9) 0.01934(10) 0.01538(9) -0.00010(9) 0.00209(6) -0.00046(10) Cl1 0.0355(7) 0.0198(6) 0.0214(6) 0.0029(5) 0.0022(5) -0.0003(6) N1 0.0198(19) 0.021(2) 0.0179(19) -0.0052(19) 0.0027(15) -0.002(2) N2 0.019(2) 0.009(2) 0.019(2) -0.0021(17) 0.0025(16) -0.0012(17) N3 0.020(2) 0.016(2) 0.017(2) -0.0005(17) 0.0037(16) 0.0004(18) N4 0.021(2) 0.013(2) 0.0158(18) 0.0013(17) 0.0035(15) 0.0021(19) N5 0.020(2) 0.012(2) 0.018(2) -0.0029(16) 0.0025(15) -0.0007(18) N6 0.047(3) 0.019(2) 0.017(2) 0.0007(19) 0.0052(19) 0.000(2) N7 0.034(2) 0.009(2) 0.019(2) 0.0014(17) 0.0011(17) -0.002(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.337(6) . ? C1 N2 1.358(6) . ? C1 Au1 2.003(5) . ? C2 C3 1.346(7) . ? C2 N2 1.388(7) . ? C2 H2 0.9500 . ? C3 N1 1.371(7) . ? C3 H3 0.9500 . ? C4 N1 1.467(6) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.319(6) . ? C5 N5 1.325(7) . ? C5 N2 1.430(6) . ? C6 N4 1.327(7) . ? C6 N6 1.363(6) . ? C6 N3 1.364(6) . ? C7 N7 1.341(6) . ? C7 N4 1.355(6) . ? C7 N5 1.361(6) . ? C8 N6 1.448(7) . ? C8 C9 1.519(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.535(8) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.511(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N6 1.458(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N7 1.451(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N7 1.454(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? Au1 Cl1 2.2976(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 105.1(4) . . ? N1 C1 Au1 126.1(3) . . ? N2 C1 Au1 128.8(3) . . ? C3 C2 N2 106.0(5) . . ? C3 C2 H2 127.0 . . ? N2 C2 H2 127.0 . . ? C2 C3 N1 107.4(5) . . ? C2 C3 H3 126.3 . . ? N1 C3 H3 126.3 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 N5 129.7(5) . . ? N3 C5 N2 113.4(4) . . ? N5 C5 N2 116.8(4) . . ? N4 C6 N6 117.8(5) . . ? N4 C6 N3 125.6(5) . . ? N6 C6 N3 116.5(5) . . ? N7 C7 N4 117.9(4) . . ? N7 C7 N5 118.3(4) . . ? N4 C7 N5 123.8(5) . . ? N6 C8 C9 110.3(5) . . ? N6 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N6 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 111.3(5) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 111.7(5) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 110.7(5) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N6 C12 C11 110.4(5) . . ? N6 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N6 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N7 C13 H13A 109.5 . . ? N7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 H14A 109.5 . . ? N7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 Au1 Cl1 178.76(13) . . ? C1 N1 C3 111.1(4) . . ? C1 N1 C4 126.1(5) . . ? C3 N1 C4 122.8(4) . . ? C1 N2 C2 110.4(4) . . ? C1 N2 C5 128.1(4) . . ? C2 N2 C5 121.5(4) . . ? C5 N3 C6 112.1(4) . . ? C6 N4 C7 115.7(4) . . ? C5 N5 C7 113.1(4) . . ? C6 N6 C8 122.2(5) . . ? C6 N6 C12 121.5(5) . . ? C8 N6 C12 114.7(4) . . ? C7 N7 C13 121.8(4) . . ? C7 N7 C14 122.4(4) . . ? C13 N7 C14 115.7(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 N2 C2 C3 N1 0.0(6) . . . . ? N6 C8 C9 C10 52.6(7) . . . . ? C8 C9 C10 C11 -51.8(7) . . . . ? C9 C10 C11 C12 52.5(7) . . . . ? C10 C11 C12 N6 -54.5(6) . . . . ? N1 C1 Au1 Cl1 50(7) . . . . ? N2 C1 Au1 Cl1 -128(6) . . . . ? N2 C1 N1 C3 -0.2(5) . . . . ? Au1 C1 N1 C3 -178.7(4) . . . . ? N2 C1 N1 C4 -179.9(4) . . . . ? Au1 C1 N1 C4 1.5(7) . . . . ? C2 C3 N1 C1 0.1(6) . . . . ? C2 C3 N1 C4 179.9(4) . . . . ? N1 C1 N2 C2 0.1(5) . . . . ? Au1 C1 N2 C2 178.6(4) . . . . ? N1 C1 N2 C5 -179.7(4) . . . . ? Au1 C1 N2 C5 -1.2(7) . . . . ? C3 C2 N2 C1 -0.1(6) . . . . ? C3 C2 N2 C5 179.8(4) . . . . ? N3 C5 N2 C1 178.5(4) . . . . ? N5 C5 N2 C1 -1.4(7) . . . . ? N3 C5 N2 C2 -1.3(6) . . . . ? N5 C5 N2 C2 178.8(4) . . . . ? N5 C5 N3 C6 0.7(7) . . . . ? N2 C5 N3 C6 -179.2(4) . . . . ? N4 C6 N3 C5 -1.4(7) . . . . ? N6 C6 N3 C5 176.5(4) . . . . ? N6 C6 N4 C7 -177.3(4) . . . . ? N3 C6 N4 C7 0.6(7) . . . . ? N7 C7 N4 C6 -178.6(4) . . . . ? N5 C7 N4 C6 1.0(7) . . . . ? N3 C5 N5 C7 0.7(7) . . . . ? N2 C5 N5 C7 -179.5(4) . . . . ? N7 C7 N5 C5 178.0(4) . . . . ? N4 C7 N5 C5 -1.6(7) . . . . ? N4 C6 N6 C8 -173.5(5) . . . . ? N3 C6 N6 C8 8.4(8) . . . . ? N4 C6 N6 C12 -8.6(8) . . . . ? N3 C6 N6 C12 173.3(5) . . . . ? C9 C8 N6 C6 108.4(6) . . . . ? C9 C8 N6 C12 -57.4(7) . . . . ? C11 C12 N6 C6 -107.5(6) . . . . ? C11 C12 N6 C8 58.5(7) . . . . ? N4 C7 N7 C13 0.2(7) . . . . ? N5 C7 N7 C13 -179.5(4) . . . . ? N4 C7 N7 C14 -176.2(5) . . . . ? N5 C7 N7 C14 4.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.416 _refine_diff_density_min -0.941 _refine_diff_density_rms 0.150 _database_code_depnum_ccdc_archive 'CCDC 915438'